Movatterモバイル変換

[0]ホーム
URL:

WO2011067184A1 - 3- (4, 5 -dihydroisoxazol- 5 -yl) benzoylpyrazole compounds and mixtures thereof with safeners - Google Patents

3- (4, 5 -dihydroisoxazol- 5 -yl) benzoylpyrazole compounds and mixtures thereof with safenersDownload PDF

Info

Publication number
WO2011067184A1
WO2011067184A1PCT/EP2010/068352EP2010068352WWO2011067184A1WO 2011067184 A1WO2011067184 A1WO 2011067184A1EP 2010068352 WEP2010068352 WEP 2010068352WWO 2011067184 A1WO2011067184 A1WO 2011067184A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
alkyl
methyl
hydrogen
ethyl
Prior art date
Application number
PCT/EP2010/068352
Other languages
German (de)
French (fr)
Inventor
Matthias Witschel
Bernd Sievernich
Ernst Baumann
Andree Van Der Kloet
Michael Rack
Rex Liebl
Original Assignee
Basf Se
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Basf SefiledCriticalBasf Se
Publication of WO2011067184A1publicationCriticalpatent/WO2011067184A1/en

Links

Classifications

Definitions

Landscapes

Abstract

1. The invention relates to a herbicidal mixture comprising a) a herbicidally-active amount of a benzoylpyrazole of formula (I), as component A, the variables being defined as follows: R1 represents halogen, C1-C4-alkyl, C1-C4-alkoxy; R2represents C1-C4-alkyl, C1-C4-halogenalkyl, C1-C4-alkoxy; R3 represents C1-C4-alkylsulfonyl; R4representshydrogen, C3-C6-alkinyl, C3-C6-halogenalkinyl; R5 represents C2-C4-alkyl, C3-C4-cycloalkyl; R6 represents hydrogen, C1-C4-alkyl; or the agriculturally suitable salts thereof; and b) an antidotally-active amount of a safener, as component B. 2. In addition, the invention relates to compounds of formula (I), the variables being defined as above except that R4 does not equal hydrogen.

Description

3 - (4 , 5 -DIHYDROISOXAZOL- 5 -YL) BENZOYLPYRAZOLVERBINDUNGEN UND IHRE MISCHUNGEN MIT SAFENERN3 - (4, 5 -DIHYDROISOXAZOLE-5-YL) BENZOYLPYRAZOL COMPOUNDS AND THEIR MIXTURES WITH SAFENERN
Beschreibungdescription
5 Die vorliegende Erfindung betrifft Mischungen herbizider Wirkstoffe und Safener.The present invention relates to mixtures of herbicidally active compounds and safeners.
Ein Teil der im chemischen Pflanzenschutz erfolgreich eingesetzten herbiziden Wirkstoffe beeinflusst die Carotinoidbiosynthese in Pflanzen, beispielsweise durch Hemmung des Enzyms 4-Hydroxy-Phenyl-Pyruvat-Dioxygenase (4-HPPD). Dadurch wirdPart of the herbicidal active ingredients successfully used in chemical crop protection influences carotenoid biosynthesis in plants, for example by inhibiting the enzyme 4-hydroxy-phenyl-pyruvate dioxygenase (4-HPPD). This will
10 die Biosynthese von Plastochinonen und indirekt von Carotinoiden unterbunden. Synthese und Funktion der Chloroplasten werden damit gestört. Als Folge kommt es zum oxidativen Abbau von Chlorophyll, was sich insbesondere in den Wachstumszonen der oberirdischen Pflanzenteile in Form deutlicher Ausbleichungen äußert.10 inhibited the biosynthesis of plastoquinones and indirectly of carotenoids. Synthesis and function of the chloroplasts are disturbed. As a result, it comes to the oxidative degradation of chlorophyll, which manifests itself in particular in the growth zones of the above-ground parts of plants in the form of significant fading.
4-HPPD-lnhibitoren und Verfahren zu ihrer Herstellung sind aus dem Stand der 4-HPPD inhibitors and processes for their preparation are known from the
15 Technik bekannt, beispielsweise aus der WO96/26206, W098/31681 , W098/31682, WO99/58509 oder WO01/46182.Known from, for example, WO96 / 26206, WO98 / 31681, WO98 / 31682, WO99 / 58509 or WO01 / 46182.
Die Kulturpflanzenverträglichkeit von 4-HPPD-lnhibitoren ist variabel. Je nach Kulturpflanze kann es daher empfehlenswert sein, 4-HPPD-lnhiboren in Kombination mit 20 sogenannten Safenern anzuwenden (W099/66795). Der Mechanismus über den ein Safener die phytotoxischen Effekte eines bestimmten Herbizids auf die Anbaupflanze verringert ist nicht immer genau bekannt.Crop compatibility of 4-HPPD inhibitors is variable. Depending on the crop, it may therefore be advisable to use 4-HPPD inhibitors in combination with 20 so-called safeners (W099 / 66795). The mechanism by which a safener reduces the phytotoxic effects of a given herbicide on the crop is not always well known.
Die Anforderungen an moderne Pflanzenschutzmittel hinsichtlich Wirksamkeit und Selektivität werden von den bekannten Herbiziden nicht umfassend erfüllt. The requirements for modern crop protection products in terms of effectiveness and selectivity are not fully met by the known herbicides.
25 25
Eine Aufgabe der vorliegenden Erfindung ist die Bereitstellung herbizider Mittel. Insbesondere sollen Mittel zur Verfügung gestellt werden, die eine hohe herbizide Wirkung aufweisen, auch bereits bei niedrigen Aufwandmengen, und deren Verträglichkeit gegenüber Kulturpflanzen für eine kommerzielle Verwertung hinreichend ist. An object of the present invention is to provide herbicidal agents. In particular, agents are to be provided which have a high herbicidal activity, even at low application rates, and their compatibility with crop plants is sufficient for commercial exploitation.
30 30
Diese und weitere Aufgaben wurden durch die im Folgenden beschriebenen herbiziden Mischungen und Verbindungen gelöst. These and other objects have been achieved by the herbicidal mixtures and compounds described below.
Die vorliegende Erfindung betrifft herbizide Mischungen, umfassendThe present invention relates to herbicidal mixtures comprising
35 a) als Komponente A eine herbizid wirksame Menge eines Benzoylpyrazols der 35 a) as component A, a herbicidally effective amount of a Benzoylpyrazols the
Formel I, Formula I,
O R1 O— N worin die Variablen folgende Bedeutungen haben:OR1 O-N wherein the variables have the following meanings:
R1 Halogen, Ci-C4-Alkyl, Ci-C4-Alkoxy;R1 is halogen, C1 -C4 -alkyl, C 1 -C4 -alkoxy;
R2 Ci-C4-Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy;R2Ci-C4-alkyl,Ci-C4-haloalkyl, Ci-C4 alkoxy;
R3 Ci-C4-Alkylsulfonyl;R3 is C 1 -C4 -alkylsulfonyl;
R4 Wasserstoff, C3-C6-Alkinyl, C3-C6-Halogenalkinyl;R4 is hydrogen, C3 -C 6 -alkynyl, C3 -C 6 -haloalkynyl;
R5 C2-C4-Alkyl, C3-C4-Cycloalkyl;R5 is C2 -C4 -alkyl, C3 -C4 -cycloalkyl;
R6 Wasserstoff, Ci-C4-Alkyl;R6 is hydrogen, C 1 -C4 -alkyl;
oder dessen landwirtschaftlich geeigneten Salzes; und or its agriculturally suitable salt; and
b) als Komponente B eine antidotisch wirksame Menge eines Safeners.b) as component B, an antidote effective amount of a safener.
Benzoylpyrazole der Formel I,Benzoylpyrazoles of the formula I,
Figure imgf000004_0001
Figure imgf000004_0001
worin die Variablen folgende Bedeutungen haben: wherein the variables have the following meanings:
R1 Halogen, Ci-C4-Alkyl, Ci-C4-Alkoxy;R1 is halogen, C1 -C4 -alkyl, C 1 -C4 -alkoxy;
R2 Ci-C4-Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy;R2Ci-C4-alkyl,Ci-C4-haloalkyl, Ci-C4 alkoxy;
R3 Ci-C4-Alkylsulfonyl;R3 is C 1 -C4 -alkylsulfonyl;
R4 C3-C6-Alkinyl, C3-C6-Halogenalkinyl;R4 is C3 -C6 alkynyl, C3 -C6 haloalkynyl;
R5 C2-C4-Alkyl, C3-C4-Cycloalkyl;R5 is C2 -C4 -alkyl, C3 -C4 -cycloalkyl;
R6 Wasserstoff, Ci-C4-Alkyl;R6 is hydrogen, C 1 -C4 -alkyl;
sind neu und weisen gegenüber den aus dem Stand der Technik bekannten Verbindungen verbesserte Eigenschaften auf.are new and have improved properties over the compounds known from the prior art.
Gegenstand der vorliegenden Erfindung sind daher auch Benzoylpyrazole der Formel I, worinThe present invention therefore also benzoylpyrazoles of the formula I, wherein
R1 Halogen, Ci-C4-Alkyl, Ci-C4-Alkoxy;R1 is halogen, C1 -C4 -alkyl, C 1 -C4 -alkoxy;
R2 Ci-C4-Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy;R2Ci-C4-alkyl,Ci-C4-haloalkyl, Ci-C4 alkoxy;
R3 Ci-C4-Alkylsulfonyl;R3 is C 1 -C4 -alkylsulfonyl;
R4 Cs-Ce-Alkinyl, C3-C6-Halogenalkinyl;R4 is Cs-Ce-alkynyl, C3 -C6 -haloalkynyl;
R5 C2-C4-Alkyl, C3-C4-Cycloalkyl; undR5 is C2 -C4 -alkyl, C3 -C4 -cycloalkyl; and
R6 Wasserstoff, Ci-C4-Alkyl bedeuten.R6 is hydrogen, Ci-C4 alkyl.
Außerdem betrifft die Erfindung Verfahren zur Herstellung der erfindungsgemäßen Benzoylpyrazole der Formel I und der erfindungsgemäßen Mischungen sowie Mittel, enthaltend eine erfindungsgemäße herbizide Mischung oder eine herbizid wirksame Menge eines Benzoylpyrazols der Formel I und für die Formulierung von Pflanzenschutzmitteln übliche Hilfsmittel. Des weiteren betrifft die Erfindung Verfahren zur Bekämpfung unerwünschten Pflanzenwuchses, bei dem man eine erfindungsgemäße herbizide Mischung oder eine her- bizid wirksame Menge eines Benzoylpyrazols der Formel I auf Pflanzen, deren Samen und/oder deren Lebensraum einwirken lässt.In addition, the invention relates to processes for the preparation of the benzoylpyrazoles of the formula I and the mixtures according to the invention and compositions comprising a herbicidal mixture according to the invention or a herbicidally effective amount of a benzoylpyrazole of the formula I and for the formulation of pesticides customary auxiliaries. The invention further relates to methods for controlling undesired plant growth, in which a herbicidal mixture according to the invention or a herbicidally effective amount of a benzoylpyrazole of the formula I is allowed to act on plants, their seeds and / or their habitat.
Weitere Ausführungsformen der vorliegenden Erfindung sind den Ansprüchen, der Beschreibung und den Beispielen zu entnehmen. Es versteht sich, dass die vorstehend genannten und die nachstehend noch zu erläuternden Merkmale des erfindungsgemäßen Gegenstandes nicht nur in der jeweils angegebenen Kombination, sondern auch in anderen Kombinationen verwendbar sind, ohne den Rahmen der Erfindung zu verlassen.Further embodiments of the present invention can be taken from the claims, the description and the examples. It is understood that the features mentioned above and those yet to be explained of the subject matter according to the invention can be used not only in the particular combination specified, but also in other combinations, without departing from the scope of the invention.
Die für die Substituenten der erfindungsgemäßen Verbindungen genannten organischen Molekülteile stellen Sammelbegriffe für individuelle Aufzählungen der einzelnen Gruppenmitglieder dar. Sämtliche Kohlenwasserstoffketten, wie Alkyl, Halo(gen)alkyl, Alkenyl, Alkinyl, sowie die Alkylteile und Alkenylteile in Alkoxy, Halo(gen)alkoxy, Alky- lamino, Dialkylamino, N-Alkylsulfonylamino, Alkenyloxy, Alkinyloxy, Alkoxyamino, Alkylaminosulfonylamino, Dialkylaminosulfonylamino, Alkenylamino, Alkinylamino, N- (Alkenyl)-N-(alkyl)-amino, N-(Alkinyl)-N-(alkyl)-amino, N-(Alkoxy)-N-(alkyl)-amino, N- (Alkenyl)-N-(alkoxy)-amino oder N-(Alkinyl)-N-(alkoxy)-amino können geradkettig oder verzweigt sein.The organic molecular moieties mentioned for the substituents of the compounds according to the invention are collective terms for individual listings of the individual group members. All hydrocarbon chains, such as alkyl, halo (gen) alkyl, alkenyl, alkynyl, and the alkyl moieties and alkenyl moieties in alkoxy, halo (gen) alkoxy, Alkylamino, dialkylamino, N-alkylsulfonylamino, alkenyloxy, alkynyloxy, alkoxyamino, alkylaminosulfonylamino, dialkylaminosulfonylamino, alkenylamino, alkynylamino, N- (alkenyl) -N- (alkyl) -amino, N- (alkynyl) -N- (alkyl) - amino, N- (alkoxy) -N- (alkyl) -amino, N- (alkenyl) -N- (alkoxy) -amino or N- (alkynyl) -N- (alkoxy) -amino can be straight-chain or branched.
Das Präfix Cn-Cm- gibt die jeweilige Kohlenstoffzahl der Kohlenwasserstoffeinheit an. Sofern nicht anders angegeben tragen halogenierte Substituenten vorzugsweise ein bis fünf gleiche oder verschiedene Halogenatome, insbesondere Fluoratome oder Chloratome.The prefix Cn -Cm - indicates the particular carbon number of the hydrocarbon moiety. Unless otherwise stated, halogenated substituents preferably carry one to five identical or different halogen atoms, in particular fluorine atoms or chlorine atoms.
Die Bedeutung Halogen steht jeweils für Fluor, Chlor, Brom oder lod. The meaning halogen in each case represents fluorine, chlorine, bromine or iodine.
Ferner bedeuten beispielsweise: Furthermore, for example:
Alkyl sowie die Alkylteile beispielsweise in Alkoxy, Alkylamino, Dialkylamino, N- Alkylsulfonylamino, Alkylsulfonyl, Alkylaminosulfonylamino, Dialkylaminosulfonylamino, N-(Alkenyl)-N-(alkyl)-amino, N-(Alkinyl)-N-(alkyl)-amino, N-(Alkoxy)-N-(alkyl)-amino: gesättigte, geradkettige oder verzweigte Kohlenwasserstoffreste mit einem oder mehr C-Atomen, z.B. 1 bis 2, 1 bis 4, 2 bis 4, oder 1 bis 6 Kohlenstoffatomen, z.B. C1-C6- Alkyl wie Methyl, Ethyl, Propyl, 1 -Methylethyl, Butyl, 1 -Methylpropyl, 2-Methylpropyl, 1 ,1 -Dimethylethyl, Pentyl, 1 -Methylbutyl, 2-Methyl butyl, 3-Methylbutyl, 2,2- Dimethylpropyl, 1 -Ethylpropyl, Hexyl, 1 ,1 -Dimethylpropyl, 1 ,2-Dimethylpropyl, 1 - Alkyl and the alkyl moieties, for example, in alkoxy, alkylamino, dialkylamino, N-alkylsulfonylamino, alkylsulfonyl, alkylaminosulfonylamino, dialkylaminosulfonylamino, N- (alkenyl) -N- (alkyl) -amino, N- (alkynyl) -N- (alkyl) -amino, N- (alkoxy) -N- (alkyl) -amino: saturated, straight-chain or branched hydrocarbon radicals having one or more C atoms, eg 1 to 2, 1 to 4, 2 to 4, or 1 to 6 carbon atoms, e.g. C 1 -C 6 -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2 Dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1 -
Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4-Methylpentyl, 1 ,1 -Dimethylbutyl, 1 ,2- Dimethylbutyl, 1 ,3-Dimethylbutyl, 2,2-Dimethylbutyl, 2,3-Dimethylbutyl, 3,3- Dimethylbutyl, 1 -Ethylbutyl, 2-Ethylbutyl, 1 ,1 ,2-Trimethylpropyl, 1 ,2,2-Trimethylpropyl, 1 -Ethyl-1 -methylpropyl, 1 -Ethyl-2-methylpropyl. In einer erfindungsgemäßen Ausfüh- rungsform steht Alkyl für kleine Alkylgruppen wie Ci-C4-Alkyl. In einer anderen erfindungsgemäßen Ausführungsform steht Alkyl für größere Alkylgruppen wie Cs-Ce-Alkyl. Halogenalkyl (auch als Haloalkyl bezeichnet): einen Alkylrest wie vorstehend genannt, dessen Wasserstoffatome partiell oder vollständig durch Halogenatome wie Fluor, Chlor, Brom und/oder lod substituiert sind, z.B. Chlormethyl, Dichlormethyl, Trichlormethyl, Fluormethyl, Difluormethyl, Trifluormethyl, Chlorfluormethyl, Dichlorflu- ormethyl, Chlordifluormethyl, 2-Fluorethyl, 2-Chlorethyl, 2-Bromethyl, 2-lodethyl, 2,2- Difluorethyl, 2,2,2-Trifluorethyl, 2-Chlor-2-fluorethyl, 2-Chlor-2,2-difluorethyl, 2,2- Dichlor-2-fluorethyl, 2,2,2-Trichlorethyl, Pentafluorethyl, 2-Fluorpropyl, 3-Fluorpropyl, 2,2-Difluorpropyl, 2,3-Difluorpropyl, 2-Chlorpropyl, 3-Chlorpropyl, 2,3-Dichlorpropyl, 2- Brompropyl, 3-Brompropyl, 3,3,3-Trifluorpropyl, 3,3,3-Trichlorpropyl, 2,2,3,3,3- Pentafluorpropyl, Heptafluorpropyl, 1 -(Fluormethyl)-2-fluorethyl, 1 -(Chlormethyl)-2- chlorethyl, 1 -(Brommethyl)-2-bromethyl, 4-Fluorbutyl, 4-Chlorbutyl, 4-Brombutyl und Nonafluorbutyl.Methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl. In one embodiment of the invention, alkyl is a small alkyl group such as C 1 -C 4 -alkyl. In another embodiment of the invention, alkyl is greater alkyl groups such as Cs-Ce-alkyl. Haloalkyl (also referred to as haloalkyl): an alkyl radical as mentioned above whose hydrogen atoms are partially or fully substituted by halogen atoms such as fluorine, chlorine, bromine and / or iodine, for example chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichloroflu - ormethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2 -difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl , 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1 - (fluoromethyl) 2-fluoroethyl, 1 - (chloromethyl) -2-chloroethyl, 1 - (bromomethyl) -2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl and nonafluorobutyl.
Cycloalkyl sowie die Cycloalkylteile beispielsweise in Cycloalkoxy oder Cycloalkyl- carbonyl: monocyclische, gesättigte Kohlenwasserstoffgruppen mit drei oder mehr C- Atomen, z.B. 3 bis 6 Kohlenstoffringgliedern, wie Cyclopropyl, Cyclobutyl, Cyclopentyl und Cyclohexyl. Cycloalkyl and the cycloalkyl moieties, for example, in cycloalkoxy or cycloalkylcarbonyl: monocyclic, saturated hydrocarbon groups having three or more C atoms, e.g. 3 to 6 carbon ring members such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
Alkenyl sowie Alkenylteile beispielsweise in Alkenylamino, Alkenyloxy, N-(Alkenyl)-N- (alkyl)-amino, N-(Alkenyl)-N-(alkoxy)-amino: einfach ungesättigte, geradkettige oder verzweigte Kohlenwasserstoffreste mit zwei oder mehr C-Atomen, z. B. 2 bis 4, 2 bis 6 oder 3 bis 6 Kohlenstoffatomen und einer Doppelbindung in einer beliebigen Position, z.B. C2-C6-Alkenyl wie Ethenyl, 1 -Propenyl, 2-Propenyl, 1 -Methylethenyl, 1 -Butenyl, 2- Butenyl, 3-Butenyl, 1 -Methyl-1 -propenyl, 2-Methyl-1 -propenyl, 1 -Methyl-2-propenyl, 2- Methyl-2-propenyl, 1 -Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1 -Methyl-1 -butenyl, 2-Methyl-1 -butenyl, 3-Methyl-1 -butenyl, 1 -Methyl-2-butenyl, 2-Methyl-2-butenyl, 3- Methyl-2-butenyl, 1 -Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3-butenyl, 1 ,1 -Di- methyl-2-propenyl, 1 ,2-Dimethyl-1 -propenyl, 1 ,2-Dimethyl-2-propenyl, 1 -Ethyl-1 - propenyl, 1 -Ethyl-2-propenyl, 1 -Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5-Hexenyl, 1 -Methyl-1 -pentenyl, 2-Methyl-1 -pentenyl, 3-Methyl-1 -pentenyl, 4-Methyl-1 -pentenyl, 1 - Methyl-2-pentenyl, 2-Methyl-2-pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, 1 - Methyl-3-pentenyl, 2-Methyl-3-pentenyl, 3-Methyl-3-pentenyl, 4-Methyl-3-pentenyl, 1 - Methyl-4-pentenyl, 2-Methyl-4-pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1 ,1 - Dimethyl-2-butenyl, 1 ,1 -Dimethyl-3-butenyl, 1 ,2-Dimethyl-1 -butenyl, 1 ,2-Dimethyl-2- butenyl, 1 ,2-Dimethyl-3-butenyl, 1 ,3-Dimethyl-1 -butenyl, 1 ,3-Dimethyl-2-butenyl, 1 ,3- Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3-Dimethyl-1 -butenyl, 2,3-Dimethyl-2- butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-1 -butenyl, 3,3-Dimethyl-2-butenyl, 1 - Ethyl-1 -butenyl, 1 -Ethyl-2-butenyl, 1 -Ethyl-3-butenyl, 2-Ethyl-1 -butenyl, 2-Ethyl-2- butenyl, 2-Ethyl-3-butenyl, 1 ,1 ,2-Trimethyl-2-propenyl, 1 -Ethyl-1 -methyl-2-propenyl, 1 - Ethyl-2-methyl-1 -propenyl, 1 -Ethyl-2-methyl-2-propenyl. Alkenyl and alkenyl moieties, for example, in alkenylamino, alkenyloxy, N- (alkenyl) -N- (alkyl) -amino, N- (alkenyl) -N- (alkoxy) -amino: monounsaturated, straight-chain or branched hydrocarbon radicals having two or more carbon atoms. Atoms, z. 2 to 4, 2 to 6 or 3 to 6 carbon atoms and a double bond in any position, e.g. C2-C6 alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1 - Methyl 2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl 1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3 butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1 -hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1 - pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1 - Dimethyl-2-butenyl, 1, 1-dimethyl 3-butenyl, 1, 2-dimethyl-1-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3-dimethyl-1-butenyl, 1, 3-dimethyl -2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl 3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2 Ethyl 1 -butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl 2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl.
Cycloalkenyl: monocyclische, einfach ungesättigte Kohlenwasserstoffgruppen mit 3 bis 6, vorzugsweise 5 bis 6 Kohlenstoffringgliedern, wie Cyclopenten-1 -yl, Cyclopen- ten-3-yl, Cyclohexen-1 -yl, Cyclohexen-3-yl, Cyclohexen-4-yl. Alkinyl sowie Alkinylteile beispielsweise in Alkinyloxy, Alkinylamino, N-(Alkinyl)-N- (alkyl)-amino oder N-(Alkinyl)-N-(alkoxy)-amino: geradkettige oder verzweigte Kohlenwasserstoffgruppen mit zwei oder mehr C-Atomen, z. B. 2 bis 4, 2 bis 6, oder 3 bis 6 Kohlenstoffatomen und einer Dreifachbindung in beliebiger Position, z.B. C2-C6-Alkinyl wie Ethinyl, 1 -Propinyl, 2-Propinyl, 1 -Butinyl, 2-Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, 1 -Pentinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, 1 -Methyl-2-butinyl, 1 -Methyl-3-butinyl, 2- Methyl-3-butinyl, 3-Methyl-1 -butinyl, 1 ,1 -Dimethyl-2-propinyl, 1 -Ethyl-2-propinyl, 1 - Hexinyl, 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5-Hexinyl, 1 -Methyl-2-pentinyl, 1 -Methyl-3- pentinyl, 1 -Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3-Methyl-1 - pentinyl, 3-Methyl-4-pentinyl, 4-Methyl-1 -pentinyl, 4-Methyl-2-pentinyl, 1 ,1 -Dimethyl-2- butinyl, 1 ,1 -Dimethyl-3-butinyl, 1 ,2-Dimethyl-3-butinyl, 2,2-Dimethyl-3-butinyl, 3,3- Dimethyl-1 -butinyl, 1 -Ethyl-2-butinyl, 1 -Ethyl-3-butinyl, 2-Ethyl-3-butinyl, 1 -Ethyl-1 - methyl-2-propinyl.Cycloalkenyl: monocyclic, monounsaturated hydrocarbon groups having 3 to 6, preferably 5 to 6 carbon ring members, such as cyclopentene-1-yl, cyclopentene-3-yl, cyclohexene-1-yl, cyclohexen-3-yl, cyclohexen-4-yl , Alkynyl and alkynyl moieties, for example, in alkynyloxy, alkynylamino, N- (alkynyl) -N- (alkyl) -amino or N- (alkynyl) -N- (alkoxy) -amino: straight-chain or branched hydrocarbon groups having two or more carbon atoms, eg , B. 2 to 4, 2 to 6, or 3 to 6 carbon atoms and a triple bond in any position, for example C 2 -C 6 alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl , 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3 -Methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2 pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl , 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2 -Dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2 propynyl.
Halogenalkinyl: Alkinyl, wie vorstehend definiert, das partiell oder vollständig durch Fluor, Chlor, Brom und/oder lod substituiert ist, insbesondere C3-C6-Halogenalkinyle wie 1 ,1 -Difluoroprop-2-yn-1 -yl, 3-lodoprop-2-yn-1 -yl, 4-Fluorobut-2-yn-1 -yl, 4- Chlorobut-2-yn-1 -yl, 1 ,1 -Difluorobut-2-yn-1 -yl, 4-lodobut-3-yn-1 -yl, 5-Fluoropent-3-yn-1 - yl, 5-lodopent-4-yn-1 -yl, 6-Fluorohex-4-yn-1 -yl oder 6-lodohex-5-yn-1 -yl. Haloalkynyl: alkynyl, as defined above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, in particular C 3 -C 6 -haloalkynyls, such as 1,1-difluoroprop-2-yn-1-yl, 3-iodopropylene 2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl, 4-iodobutyl 3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl, 6-fluoro-hex-4-yn-1-yl or 6-iodo-hex-5 yn-1-yl.
Alkoxy: Alkyl, wie vorstehend definiert, das über ein O-Atom gebunden ist: z. B. Me- thoxy, Ethoxy, n-Propoxy, 1 -Methylethoxy, Butoxy, 1 -Methylpropoxy, 2-Methylpropoxy oder 1 ,1 -Dimethylethoxy, Pentoxy, 1 -Methylbutoxy, 2-Methylbutoxy, 3-Methylbutoxy, 1 ,1 -Dimethylpropoxy, 1 ,2-Dimethylpropoxy, 2,2-Dimethylpropoxy, 1 -Ethylpropoxy, He- xoxy, 1 -Methylpentoxy, 2-Methylpentoxy, 3-Methylpentoxy, 4-Methylpentoxy, 1 ,1 - Dimethylbutoxy, 1 ,2-Dimethylbutoxy, 1 ,3-Dimethylbutoxy, 2,2-Dimethylbutoxy, 2,3- Dimethylbutoxy, 3,3-Dimethylbutoxy, 1 -Ethylbutoxy, 2-Ethyl butoxy, 1 ,1 ,2- Alkoxy: alkyl, as defined above, which is bonded via an oxygen atom: z. Methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1 - Dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2
Trimethylpropoxy, 1 ,2,2-Trimethylpropoxy, 1 -Ethyl-1 -methylpropoxy oder 1 -Ethyl-2- methylpropoxy.Trimethylpropoxy, 1, 2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy.
Aryl bezeichnet einen ein- bis dreikernigen aromatischen Carbocyclus mit 6 bis 14 Ringgliedern, beispielsweise Phenyl, Naphthyl und Anthracenyl. Aryl denotes a mono- to trinuclear aromatic carbocycle having 6 to 14 ring members, for example phenyl, naphthyl and anthracenyl.
Heteroaryl bezeichnet ein 5- oder 6-gliedriges aromatisches Ringsystem mit ein bis vier Stickstoffatomen oder mit ein bis drei Stickstoffatomen und einem Sauerstoff- oder Schwefelatom, oder mit einem Sauerstoff- oder Schwefelatom. Heteroaryl denotes a 5- or 6-membered aromatic ring system having one to four nitrogen atoms or having one to three nitrogen atoms and one oxygen or sulfur atom, or having one oxygen or sulfur atom.
Heterocyclyl bezeichnet einen gesättigten, partiell ungesättigten oder aromatischen heterocyclischer Ring mit drei oder mehr C-Atomen, z.B. 3-, 4-, 5- oder 6-gliedriger heterocyclischer Ring, der ein bis vier gleiche oder verschiedene Heteroatome, ausgewählt aus der Gruppe Sauerstoff, Schwefel und Stickstoff enthält, und über C oder N gebunden sein kann; wobei ein Schwefel im Heterocyclyl zu S=0 oder S(=0)2 oxidiert sein kann, und wobei mit einem ankondensierten Phenylring oder mit einem C3-C6- Carbocyclus oder mit einem weiteren 5- bis 6-gliedrigen Heterocyclus ein bicyclisches Ringsystem ausgebildet werden kann. Die Benzoylpyrazole der Formel I können, je nach Substitutionsmuster, ein oder mehrere Chiralitätszentren enthalten. Die erfindungsgemäßen Verbindungen können daher als reine Enantiomere oder Diastereomere oder als Enantiomeren- oder Diaste- reomerengemische vorliegen. Gegenstand der Erfindung sind sowohl die reinen Enantiomeren oder Diastereomeren als auch deren Gemische.Heterocyclyl denotes a saturated, partially unsaturated or aromatic heterocyclic ring having three or more C atoms, for example a 3-, 4-, 5- or 6-membered heterocyclic ring which contains one to four identical or different heteroatoms selected from the group consisting of oxygen, Containing sulfur and nitrogen, and may be bonded via C or N; wherein a sulfur in the heterocyclyl may be oxidized to S = O or S (= O) 2, and wherein a bicyclic ring system is formed with a fused-on phenyl ring or with a C3-C6 carbocycle or with another 5- to 6-membered heterocycle can. The benzoylpyrazoles of the formula I can, depending on the substitution pattern, contain one or more chiral centers. The compounds according to the invention can therefore be present as pure enantiomers or diastereomers or as mixtures of enantiomers or diastereomers. The invention relates to both the pure enantiomers or diastereomers and mixtures thereof.
Die Benzoylpyrazole der Formel I können auch in Form der N-Oxide und/oder ihrer landwirtschaftlich brauchbaren Salze vorliegen, wobei es auf die Art des Salzes in der Regel nicht ankommt. Im Allgemeinen kommen die Salze derjenigen Kationen oder die Säureadditionssalze derjenigen Säuren in Betracht, deren Kationen, beziehungsweise Anionen, die herbizide Wirkung der Benzoylpyrazole der Formel I nicht negativ beeinträchtigen. The benzoylpyrazoles of the formula I can also be present in the form of the N-oxides and / or their agriculturally useful salts, wherein the nature of the salt generally does not matter. In general, the salts of those cations or the acid addition salts of those acids come into consideration whose cations, or anions, do not adversely affect the herbicidal action of the benzoylpyrazoles of the formula I.
Es kommen als Kationen insbesondere Ionen der Alkalimetalle, vorzugsweise Lithium, Natrium oder Kalium, der Erdalkalimetalle, vorzugsweise Calcium oder Magnesium, und der Übergangsmetalle, vorzugsweise Mangan, Kupfer, Zink oder Eisen in Betracht. Ebenso kann als Kation Ammonium verwendet werden, wobei hier ge- wünschtenfalls ein bis vier Wasserstoffatome durch Ci-C4-Alkyl, Hydroxy-Ci-C4-alkyl, Ci-C4-Alkoxy-Ci-C4-alkyl, Hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, Phenyl oder Benzyl ersetzt sein können, vorzugsweise Ammonium, Dimethylammonium, Diisopropylammo- nium, Tetramethylammonium, Tetrabutylammonium, 2-(2-Hydroxyeth-1 -oxy)eth-1 - ylammonium, Di(2-hydroxyeth-1 -yl)ammonium, Tnmethylbenzylammonium. Des Weiteren kommen Phosphoniumionen, Sulfoniumionen, vorzugsweise Tri(Ci-C4- alkyl)sulfonium oder Sulfoxoniumionen, vorzugsweise Tri(Ci-C4-alkyl)sulfoxonium, in Betracht. In particular, ions of the alkali metals, preferably lithium, sodium or potassium, the alkaline earth metals, preferably calcium or magnesium, and the transition metals, preferably manganese, copper, zinc or iron are suitable as cations. It is likewise possible to use ammonium as cation, in which case one to four hydrogen atoms are optionally substituted by C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, hydroxyC 1 -C 4 -alkyl. alkoxy-C 1 -C 4 -alkyl, phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2- (2-hydroxyeth-1-oxy) eth-1-ylammonium, di (2-hydroxyeth -1 -yl) ammonium, methylbenzylammonium. Further suitable are phosphonium ions, sulfonium ions, preferably tri (C 1 -C 4 -alkyl) sulfonium or sulfoxonium ions, preferably tri (C 1 -C 4 -alkyl) sulfoxonium.
Anionen von brauchbaren Säureadditionsalzen sind in erster Linie Chlorid, Bromid, Fluorid, Hydrogensulfat, Sulfat, Dihydrogenphosphat, Hydrogenphosphat, Nitrat, Hydrogencarbonat, Carbonat, Hexafluorosilikat, Hexafluorophosphat, Benzoat sowie die Anionen von Ci-C4-Alkansäuren, vorzugsweise Formiat, Acetat, Propionat, Butyrat oder Trifluoracetat. Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate, Butyrate or trifluoroacetate.
Als Komponente A) der erfindungsgemäßen herbiziden Mischung eignen sich beispielsweise die Verbindungen der Formeln 1.1 (= Verbindungen der Formel I mit R3 = CH3SO2- und R6, R4 = Wasserstoff), insbesondere die Verbindungen 1.1.1 -1.1 .560, gemäß Tabelle 1 , wobei jede Zeile der Tabelle 1 einer Verbindung der Formel I entspricht.As component A) of the herbicidal mixture according to the invention are, for example, the compounds of formulas 1.1 (= compounds of formula I with R3 = CH3 SO 2 and R6 , R4 = hydrogen), in particular the compounds 1.1.1 -1.1 .560, according to Table 1, wherein each row of Table 1 corresponds to a compound of formula I.
O R O— N O R O-N
1.1 Tabelle 1:1.1 Table 1:
Figure imgf000009_0001
Figure imgf000010_0001
Figure imgf000011_0001
Nr. R R2 R5 *.101 CH3- CH3- (CH3)2CH-.102 CH3- C2H5- (CH3)2CH-.103 CH3- CH3CH2CH2- (CH3)2CH-.104 CH3- (CH3)2CH- (CH3)2CH-.105 CH3- C2H5CH2CH2- (CH3)2CH-.106 CH3- (CH3)2CHCH2- (CH3)2CH-.107 CH3- C2H5(CH3)CH- (CH3)2CH-.108 CH3- (CH3)3C- (CH3)2CH-.109 CH3- CFH2- (CH3)2CH-.1 10 CH3- CCIH2- (CH3)2CH-.1 1 1 CH3- CF2H- (CH3)2CH-.1 12 CH3- CC H- (CH3)2CH-.1 13 CH3- CH30- (CH3)2CH-.1 14 CH3- C2H50- (CH3)2CH-.1 15 CH3- CH3CH2CH20- (CH3)2CH-.1 16 CH3- (CH3)2CHO- (CH3)2CH-.1 17 CH3- C2H5CH2CH20- (CH3)2CH-.1 18 CH3- (CH3)2CHCH20- (CH3)2CH-.1 19 CH3- C2H5(CH3)CHO- (CH3)2CH-.120 CH3- (CH3)3CO- (CH3)2CH-.121 CH3- CH3- (CH3)3C-.122 CH3- C2H5- (CH3)3C-.123 CH3- CH3CH2CH2- (CH3)3C-.124 CH3- (CH3)2CH- (CH3)3C-.125 CH3- C2H5CH2CH2- (CH3)3C-.126 CH3- (CH3)2CHCH2- (CH3)3C-.127 CH3- C2H5(CH3)CH- (CH3)3C-.128 CH3- (CH3)3C- (CH3)3C-.129 CH3- CFH2- (CH3)3C-.130 CH3- CCIH2- (CH3)3C-.131 CH3- CF2H- (CH3)3C-.132 CH3- CC H- (CH3)3C-.133 CH3- CH30- (CH3)3C-.134 CH3- C2H50- (CH3)3C-
Figure imgf000013_0001
Figure imgf000014_0001
Figure imgf000015_0001
Nr. R R2 R5 *.237 C2H5- C2H5CH2CH20- C3H5-.238 C2H5- (CH3)2CHCH20- C3H5-.239 C2H5- C2H5(CH3)CHO- C3H5-.240 C2H5- (CH3)3CO- C3H5-.241 (CH3)2CH- CH3- C2H5-.242 (CH3)2CH- C2H5- C2H5-.243 (CH3)2CH- CH3CH2CH2- C2H5-.244 (CH3)2CH- (CH3)2CH- C2H5-.245 (CH3)2CH- C2H5CH2CH2- C2H5-.246 (CH3)2CH- (CH3)2CHCH2- C2H5-.247 (CH3)2CH- C2H5(CH3)CH- C2H5-.248 (CH3)2CH- (CH3)3C- C2H5-.249 (CH3)2CH- CFH2- C2H5-.250 (CH3)2CH- CCIH2- C2H5-.251 (CH3)2CH- CF2H- C2H5-.252 (CH3)2CH- CC H- C2H5-.253 (CH3)2CH- CH30- C2H5-.254 (CH3)2CH- C2H50- C2H5-.255 (CH3)2CH- CH3CH2CH20- C2H5-.256 (CH3)2CH- (CH3)2CHO- C2H5-.257 (CH3)2CH- C2H5CH2CH20- C2H5-.258 (CH3)2CH- (CH3)2CHCH20- C2H5-.259 (CH3)2CH- C2H5(CH3)CHO- C2H5-.260 (CH3)2CH- (CH3)3CO- C2H5-.261 (CH3)2CH- CH3- (CH3)2CH-.262 (CH3)2CH- C2H5- (CH3)2CH-.263 (CH3)2CH- CH3CH2CH2- (CH3)2CH-.264 (CH3)2CH- (CH3)2CH- (CH3)2CH-.265 (CH3)2CH- C2H5CH2CH2- (CH3)2CH-.266 (CH3)2CH- (CH3)2CHCH2- (CH3)2CH-.267 (CH3)2CH- C2H5(CH3)CH- (CH3)2CH-.268 (CH3)2CH- (CH3)3C- (CH3)2CH-.269 (CH3)2CH- CFH2- (CH3)2CH-.270 (CH3)2CH- CCIH2- (CH3)2CH- Nr. R R2 R5 *.271 (CH3)2CH- CF2H- (CH3)2CH-.272 (CH3)2CH- CCI2H- (CH3)2CH-.273 (CH3)2CH- CH30- (CH3)2CH-.274 (CH3)2CH- C2H50- (CH3)2CH-.275 (CH3)2CH- CH3CH2CH20- (CH3)2CH-.276 (CH3)2CH- (CH3)2CHO- (CH3)2CH-.277 (CH3)2CH- C2H5CH2CH20- (CH3)2CH-.278 (CH3)2CH- (CH3)2CHCH20- (CH3)2CH-.279 (CH3)2CH- C2H5(CH3)CHO- (CH3)2CH-.280 (CH3)2CH- (CH3)3CO- (CH3)2CH-.281 (CH3)2CH- CH3- (CH3)3C-.282 (CH3)2CH- C2H5- (CH3)3C-.283 (CH3)2CH- CH3CH2CH2- (CH3)3C-.284 (CH3)2CH- (CH3)2CH- (CH3)3C-.285 (CH3)2CH- C2H5CH2CH2- (CH3)3C-.286 (CH3)2CH- (CH3)2CHCH2- (CH3)3C-.287 (CH3)2CH- C2H5(CH3)CH- (CH3)3C-.288 (CH3)2CH- (CH3)3C- (CH3)3C-.289 (CH3)2CH- CFH2- (CH3)3C-.290 (CH3)2CH- CCIH2- (CH3)3C-.291 (CH3)2CH- CF2H- (CH3)3C-.292 (CH3)2CH- CCI2H- (CH3)3C-.293 (CH3)2CH- CH30- (CH3)3C-.294 (CH3)2CH- C2H50- (CH3)3C-.295 (CH3)2CH- CH3CH2CH20- (CH3)3C-.296 (CH3)2CH- (CH3)2CHO- (CH3)3C-.297 (CH3)2CH- C2H5CH2CH20- (CH3)3C-.298 (CH3)2CH- (CH3)2CHCH20- (CH3)3C-.299 (CH3)2CH- C2H5(CH3)CHO- (CH3)3C-.300 (CH3)2CH- (CH3)3CO- (CH3)3C-.301 (CH3)2CH- CH3- C3H5-.302 (CH3)2CH- C2H5- C3H5-.303 (CH3)2CH- CH3CH2CH2- C3H5-.304 (CH3)2CH- (CH3)2CH- C3H5-
Figure imgf000018_0001
Nr. R R2 R5 *.339 CHsO- C2H5(CH3)CHO- C2H5-.340 CHsO- (CH3)3CO- C2H5-.341 CHsO- CH3- (CH3)2CH-.342 CHsO- C2H5- (CH3)2CH-.343 CHsO- CH3CH2CH2- (CH3)2CH-.344 CHsO- (CH3)2CH- (CH3)2CH-.345 CHsO- C2H5CH2CH2- (CH3)2CH-.346 CHsO- (CH3)2CHCH2- (CH3)2CH-.347 CHsO- C2H5(CH3)CH- (CH3)2CH-.348 CHsO- (CH3)3C- (CH3)2CH-.349 CHsO- CFH2- (CH3)2CH-.350 CHsO- CCIH2- (CH3)2CH-.351 CHsO- CF2H- (CH3)2CH-.352 CHsO- CC H- (CH3)2CH-.353 CHsO- CH30- (CH3)2CH-.354 CHsO- C2H50- (CH3)2CH-.355 CHsO- CH3CH2CH20- (CH3)2CH-.356 CHsO- (CH3)2CHO- (CH3)2CH-.357 CHsO- C2H5CH2CH20- (CH3)2CH-.358 CHsO- (CH3)2CHCH20- (CH3)2CH-.359 CHsO- C2H5(CH3)CHO- (CH3)2CH-.360 CHsO- (CH3)3CO- (CH3)2CH-.361 CHsO- CH3- (CH3)3C-.362 CHsO- C2H5- (CH3)3C-.363 CHsO- CH3CH2CH2- (CH3)3C-.364 CHsO- (CH3)2CH- (CH3)3C-.365 CHsO- C2H5CH2CH2- (CH3)3C-.366 CHsO- (CH3)2CHCH2- (CH3)3C-.367 CHsO- C2H5(CH3)CH- (CH3)3C-.368 CHsO- (CH3)3C- (CH3)3C-.369 CHsO- CFH2- (CH3)3C-.370 CHsO- CCIH2- (CH3)3C-.371 CHsO- CF2H- (CH3)3C-.372 CHsO- CC H- (CH3)3C-
Figure imgf000020_0001
Figure imgf000021_0001
Figure imgf000022_0001
Nr. R R2 R5 *.475 C2H50- CH3CH2CH20- C3H5-.476 C2H50- (CH3)2CHO- C3H5-.477 C2H50- C2H5CH2CH20- C3H5-.478 C2H50- (CH3)2CHCH20- C3H5-.479 C2H50- C2H5(CH3)CHO- C3H5-.480 C2H50- (CH3)3CO- C3H5-.481 (CH3)2CHO- CH3- C2H5-.482 (CH3)2CHO- C2H5- C2H5-.483 (CH3)2CHO- CH3CH2CH2- C2H5-.484 (CH3)2CHO- (CH3)2CH- C2H5-.485 (CH3)2CHO- C2H5CH2CH2- C2H5-.486 (CH3)2CHO- (CH3)2CHCH2- C2H5-.487 (CH3)2CHO- C2H5(CH3)CH- C2H5-.488 (CH3)2CHO- (CH3)3C- C2H5-.489 (CH3)2CHO- CFH2- C2H5-.490 (CH3)2CHO- CCIH2- C2H5-.491 (CH3)2CHO- CF2H- C2H5-.492 (CH3)2CHO- CCI2H- C2H5-.493 (CH3)2CHO- CH30- C2H5-.494 (CH3)2CHO- C2H50- C2H5-.495 (CH3)2CHO- CH3CH2CH20- C2H5-.496 (CH3)2CHO- (CH3)2CHO- C2H5-.497 (CH3)2CHO- C2H5CH2CH20- C2H5-.498 (CH3)2CHO- (CH3)2CHCH20- C2H5-.499 (CH3)2CHO- C2H5(CH3)CHO- C2H5-.500 (CH3)2CHO- (CH3)3CO- C2H5-.501 (CH3)2CHO- CH3- (CH3)2CH-.502 (CH3)2CHO- C2H5- (CH3)2CH-.503 (CH3)2CHO- CH3CH2CH2- (CH3)2CH-.504 (CH3)2CHO- (CH3)2CH- (CH3)2CH-.505 (CH3)2CHO- C2H5CH2CH2- (CH3)2CH-.506 (CH3)2CHO- (CH3)2CHCH2- (CH3)2CH-.507 (CH3)2CHO- C2H5(CH3)CH- (CH3)2CH-.508 (CH3)2CHO- (CH3)3C- (CH3)2CH- Nr. R R2 R5 *.509 (CH3)2CHO- CFH2- (CH3)2CH-.510 (CH3)2CHO- CCIH2- (CH3)2CH-.51 1 (CH3)2CHO- CF2H- (CH3)2CH-.512 (CH3)2CHO- CCI2H- (CH3)2CH-.513 (CH3)2CHO- CH30- (CH3)2CH-.514 (CH3)2CHO- C2H50- (CH3)2CH-.515 (CH3)2CHO- CH3CH2CH20- (CH3)2CH-.516 (CH3)2CHO- (CH3)2CHO- (CH3)2CH-.517 (CH3)2CHO- C2H5CH2CH20- (CH3)2CH-.518 (CH3)2CHO- (CH3)2CHCH20- (CH3)2CH-.519 (CH3)2CHO- C2H5(CH3)CHO- (CH3)2CH-.520 (CH3)2CHO- (CH3)3CO- (CH3)2CH-.521 (CH3)2CHO- CH3- (CH3)3C-.522 (CH3)2CHO- C2H5- (CH3)3C-.523 (CH3)2CHO- CH3CH2CH2- (CH3)3C-.524 (CH3)2CHO- (CH3)2CH- (CH3)3C-.525 (CH3)2CHO- C2H5CH2CH2- (CH3)3C-.526 (CH3)2CHO- (CH3)2CHCH2- (CH3)3C-.527 (CH3)2CHO- C2H5(CH3)CH- (CH3)3C-.528 (CH3)2CHO- (CH3)3C- (CH3)3C-.529 (CH3)2CHO- CFH2- (CH3)3C-.530 (CH3)2CHO- CCIH2- (CH3)3C-.531 (CH3)2CHO- CF2H- (CH3)3C-.532 (CH3)2CHO- CCI2H- (CH3)3C-.533 (CH3)2CHO- CH30- (CH3)3C-.534 (CH3)2CHO- C2H50- (CH3)3C-.535 (CH3)2CHO- CH3CH2CH20- (CH3)3C-.536 (CH3)2CHO- (CH3)2CHO- (CH3)3C-.537 (CH3)2CHO- C2H5CH2CH20- (CH3)3C-.538 (CH3)2CHO- (CH3)2CHCH20- (CH3)3C-.539 (CH3)2CHO- C2H5(CH3)CHO- (CH3)3C-.540 (CH3)2CHO- (CH3)3CO- (CH3)3C-.541 (CH3)2CHO- CH3- C3H5-.542 (CH3)2CHO- C2H5- C3H5- Nr. R R2 R5 *
Figure imgf000009_0001
Figure imgf000010_0001
Figure imgf000011_0001
No. RR2 R5 * .101 CH3 -. CH3 - (CH3)2 CH-CH3 .102 - C2H5(CH3)2 CH-CH3 .103 - CH3CH2CH2-(CH3)2 CH- .104 CH3 - (CH3 )2 CH- (CH3 )2 CH-.105 CH3 --C2 H 5 CH2 CH2 - (CH3 )2 CH-.106 CH3 - (CH3 )2 CHCH2 - (CH3 )2 CH-.107 CH3 - C2 H5 (CH3 ) CH- (CH3 )2 CH-.108 CH3 - (CH3 )3 C- (CH3 )2 CH-.109 CH3 -CFH2 - (CH3)2 CH-CH 10 .13 - CCIH2- (CH3)2 CH-.1 1 1 CH3 - CF2H- (CH3)2 CH-CH 12 .13 - CC H- ( CH3 )2 CH-.1 13 CH3 - CH3 O- (CH3 )2 CH-.1 14 CH3 - C2 H5 O- (CH3 )2 CH-.1 15 CH3 -CH3 CH2 CH2 O- (CH3 )2 CH-. 1 CH3 - (CH3 )2 CHO- (CH3 )2 CH-. 1 17 CH3 --C2 H5 CH2 CH2 O- (CH3 )2 CH-.1 18 CH3 - (CH3 )2 CHCH2 O- (CH3 )2 CH-.1 19 CH3 - C2 H5 (CH3 ) CHO- (CH3 )2 CH-. 120 CH3 - (CH3 )3 CO- (CH3 )2 CH-.121 CH3 - CH3 - (CH3 )3 C-.122 CH3 --C 2 H 5 - (CH3 )3 C-.123 CH3 -CH3 CH2CH2-(CH3)3 C-.124 CH3 - (CH3)2 CH- (CH3)3 C-CH3 .125 - C2H5CH2CH2- (CH3)3 C-CH3 .126 - (CH3 )2 CHCH2 - (CH3 )3 C-.127 C H3 - C2 H5 (CH3) CH- (CH3)3 C-.128 CH3 - (CH3)3 C- (CH3)3 C-CH3 .129 - CFH2 - (CH3 )3 C-CH3 .130 - CCIH2- (CH3)3 C-CH3 .131 - CF2H- (CH3)3 C-CH3 .132 - CC H- (CH3)3 C-CH .1333 - CH3 O- (CH3 )3 C-.134 CH3 - C2 H5 O- (CH3 )3 C-
Figure imgf000013_0001
Figure imgf000014_0001
Figure imgf000015_0001
Nr. RR2 R5 * .237 C2H5 C2H5 CH2 CH2 0-C3 H5 .238 C2H5 (CH3)2 CHCH2 0-C3 H5 .239 C2H5 C2 H5 (CH3) CHO C3 H5-.240 C2H5(CH3)3 CO- C3 H5-.241 (CH3)2 CH- CH3 - C2H5-.242 (CH3)2 CH- C2H5 C2H5 .243 (CH3 )2 CH-CH3 CH2 CH2 -C2 H 5 -244 (CH3 )2 CH- (CH3 )2 CH-C2H5-.245 (CH3 )2 CH-C2H5CH2 CH 2 -C2 H 5 -246 (CH3)2 CH- (CH3)2 CHCH2 - C2H5-.247 (CH3)2 CH- C2 H5 (CH3) CH- C2H5-.248 (CH3)2 CH- (CH3)3 C- C2H5-.249 (CH3)2 CH- CFH2 - C2H5-.250 (CH3)2 CH- CCIH2- C2H5-.251 (CH3)2 CH- CF2 H C2H5-.252 (CH3)2 CH- H C2H5 CC-.253 (CH3)2 CH- CH3 0- C2H5-.254 (CH3)2 CH- C2 H5 0- C2H5-.255 (CH3)2 CH CH3 CH2 CH2 O-C2H5-.256 (CH3 )2 CH- (CH3 )2 CHO-C2 H5 -.257 (CH3 )2 CH-C2 H5 CH2 CH2 O-C2H5-.258 (CH3 )2 CH- (CH3 )2 CHCH2 O-C2H5-.259 (CH3 )2 CH- C2 H5 (CH3 ) CHO- C2 H5 -.260 (CH3 )2 CH- (CH2 Cl2 )3)3 CO- C2H5-.261 (CH3)2 CH- CH3 - (CH3)2 CH-.262 (CH3)2 CH- C2H5 (CH3)2 CH-.263 (CH3)2 CH-CH3 CH 2CH2- (CH3)2 CH-.264 (CH3)2 CH- (CH3)2 CH- (CH3)2 CH-.265 (CH3)2 CH- C2H5CH2CH2- (CH3)2 CH- .266 (CH3 )2 CH- (CH3 )2 CHCH2 - (CH3 )2 CH-.267 (CH3 )2 CH- C2 H5 (CH3 ) CH- (CH3 )2 CH- .268 (CH3 )2 CH- (CH3 )3 C- (CH3 )2 CH-.269 (CH3 )2 CH- CFH2 - (CH3 )2 CH-.270 (CH3 )2 CH CCIH2- (CH3 )2 CH- No. RR2 R5 * .271 (CH3 )2 CH-CF2 H- (CH3 )2 CH-.272 (CH3 )2 CH-CCI2 H- (CH3 )2 CH-.273 ( CH3 )2 CH-CH3 O- (CH3 )2 CH-.274 (CH3 )2 CH- C2 H5 O- (CH3 )2 CH-.755 (CH3 )2 CH- CH3 CH2 CH2 O- (CH3 )2 CH-.276 (CH3 )2 CH- (CH3 )2 CHO- (CH3 )2 CH-.277 (CH3 )2 CH- C2 H5 CH2 CH2 O- (CH3 )2 CH-.278 (CH3 )2 CH- (CH3 )2 CHCH2 O- (CH3 )2 CH-.279 (CH3 )2 CH- C2 H5 (CH3) CHO (CH3)2 CH-.280 (CH3)2 CH- (CH3)3 CO- (CH3)2 CH-.281 (CH3)2 CH- CH3 - (CH3 )3 C-.282 (CH3 )2 CH-C2 H 5 - (CH3 )3 C-.283 (CH3 )2 CH-CH3 CH2 CH2 - (CH3 )3 C-.284 (CH3)2 CH- (CH3)2 CH- (CH3)3 C-.285 (CH3)2 CH- C2 H5CH2 CH2 - (CH3)3 C-.286 (CH3)2 CH- (CH3 )2 CHCH2 - (CH3 )3 C-.287 (CH3 )2 CH- C2 H5 (CH3 ) CH- (CH3 )3 C-.288 (CH3 )2 CH- (CH3 )3 C- (CH3 )3 C-.289 (CH3 )2 CH- CFH2 - (CH3 )3 C-.290 (CH3 )2 CH- CCIH2 - (CH3 )3 C-.291 (CH3 )2 CH- CF2 H- (CH3 )3 C-.292 (CH3 )2 CH-CCI2 H- (CH3 )3 C- .293 (CH3 )2 CH-CH3 O- (CH3 )3 C-.294 (CH3 )2 CH- C2 H5 O- (CH3 )3 C-.295 (CH3 )2 CH CH3 CH2 CH2 O- (CH3 )3 C-.296 (CH3 )2 CH- (CH3 )2 CHO- (CH3 )3 C-.297 (CH3 )2 CH- C2 H5 CH2 CH2 O- (CH3 )3 C-.298 (CH3 )2 CH- (CH3 )2 CHCH2 O- (CH3 )3 C-.299 (CH3 )2 CH- C2 H5 (CH3 ) CHO- (CH3 )3 C-.300 (CH3 )2 CH- (CH3 )3 CO- (CH3 )3 C-.301 (CH3 )2 CH-CH3 - C3 H5-.302 (CH3)2 CH- C2 H5C3 H5-.303 (CH3)2 CH- CH3 CH2 CH2 - C3 H5-.304 (CH3)2 CH - (CH3 )2 CH- C3 H5-
Figure imgf000018_0001
No. RR2 R5 * .339 CHsO-C2 H5 (CH3 ) CHO-C2 H5 -.340 CHsO- (CH3 )3 CO-C2 H5 -.341 CHsO-CH3 - (CH3 )2 CH- .342 CHsO- C2H5 (CH3)2 CH-.343 CHsO-CH3 CH2CH2-(CH3)2 CH-.344 CHsO- (CH3)2 CH- (CH3)2 CH-.345 CHsO- C2H5CH2CH2- (CH3)2 CH-.346 CHsO- (CH3)2 CHCH2 - (CH3)2 CH-.347 CHsO- C2 H5 (CH3) CH- (CH3)2 CH-. 348 CHsO- (CH3)3 C- (CH3)2 CH-.349 CHsO- CFH2 - (CH3)2 CH-.350 CHsO- CCIH2- (CH3)2 CH-CF2 .351 CHsO- H- (CH3)2 CH-.352 CHsO- CC H- (CH3)2 CH-CH3 .353 CHsO- 0- (CH3)2 CH-.354 CHsO- C2 H5 0- (CH3)2 CH-.355 CHsO- CH3 CH2 CH2 0- (CH3)2 CH-.356 CHsO- (CH3)2 CHO (CH3)2 CH-CH2 .357 CHsO- C2H5 CH2 O- (CH3 )2 CH-.358 CH3 O- (CH3 )2 CHCH2 O- (CH3 )2 CH-.359 CH2 SO2 C5 H5 (CH3 ) CHO- (CH3 )2 CH-.360 CHsO- (CH3)3 CO- (CH3)2 CH-.361 CHsO- CH3 - (CH3)3 C-.362 CHsO- C2H5(CH3)3 C-.363 CHSO - CH3 CH2 CH2 - (CH3 )3 C-.364 CH3 O- (CH3 )2 CH- (CH3 )3 C-.365 CH3 O-C2 H 5 CH2 CH2 - (CH3 )3 C-.366 CH3 O- (CH3 )2 CHCH2 - (CH3 )3 C-.367 CH3 O-C2 H5 (CH3 ) CH- (CH3 )3 C-.368 CH3 O- (CH3 )3 C- (CH3 )3 C-.369 CHsO- CFH2 - (CH3)3 C-.370 CHsO- CCIH2- (CH3)3 C-.371 CHsO- CF2 H- (CH3)3 C-.372 CHsO- CC H - (CH3 )3 C-
Figure imgf000020_0001
Figure imgf000021_0001
Figure imgf000022_0001
No. RR2 R5 * .475 C2 H5 O-CH3 CH2 CH2 O-C3 H5-.476 C2 H5 O- (CH3 )2 CHO-C3 H5 -477 C2 H 0-5 C2 H5 CH2 CH2 0-C3 H5 .478 C2 H5 0- (CH3)2 CHCH2 0-C3 H5 .479 C2 H5 C2 H 0-5(CH3) CHO C3 H5-.480 C2 H5 0- (CH3)3 CO- C3 H5-.481 (CH3)2 CHO CH3 - C2 H5-.482 (CH3)2 CHO2 C H5C2 H5 .483 (CH3)2 CHO CH3 CH2 CH2 - C2 H5-.484 (CH3)2 CHO (CH3)2 CH- C2 H5-.485 (CH3 )2 CHO-C2 H 5 CH2 CH2 - C2 H 5-.486 (CH3 )2 CHO- (CH3 )2 CHCH2 - C2 H 5-.487 (CH3 )2 CHO- C2 H5 (CH3 ) CH- C2 H5- .488 (CH3 )2 CHO- (CH3 )3 C- C2 H5- .489 (CH3 )2 CHO- CFH2 - C2 H5-.490 (CH3)2 CHO CCIH2 - C2 H5-.491 (CH3)2 CHO CF2 H C2 H5-.492 (CH3)2 CHO- H-2 CCI C2 H5-.493 (CH3 )2 CHO-CH3 0-C2 H5-.494 (CH3 )2 CHO-C2 H5 O-C2 H5-.495 (CH3 )2 CHO-CH3 CH2 CH2 0- C2 H5- .496 (CH3 )2 CHO- (CH3 )2 CHO- C2 H5- .497 (CH3 )2 CHO- C2 H5 CH2 CH2 0- C2 H5-.498 (CH3)2 CHO (CH3)2 CHCH2 0-C2 H5 .499 (CH3 ) CHO2 C2 H5 (CH3) CHO-C2 H5 .500 (CH3)2 CHO (CH3)3 CO- C2 H5-.501 (CH3)2 CHO CH3 - (CH3)2 CH-'502 (CH3)2 CHO2 C H5 (CH3)2 CH-.503 (CH3)2 CHO CH3 CH2 CH2 - (CH3)2 CH- .504 (CH3)2 CHO (CH3)2 CH- (CH3)2 CH-.505 (CH3)2 CHO2 C H5CH2 CH2 - (CH3)2 CH-.506 (CH3 )2 CHO- (CH3 )2 CHCH2 - (CH3 )2 CH-.507 (CH3 )2 CHO-C2 H5 (CH3 ) CH- (CH3 )2 CH-.508 (CH3 )2 CHO- (CH3 )3 C- (CH3 )2 CH- No. RR2 R5 * .509 (CH3 )2 CHO-CFH2 - (CH3 )2 CH-.510 (CH3 )2 CHO-CCIH2 - (CH3 )2 CH-.51 1 (CH3 )2 CHO-CF2 H- (CH3 )2 CH-.512 (CH3 )2 CHO-CCI2 H- (CH3 )2 CH-.513 (CH3 )2 CHO-CH3 O- ( CH3 )2 CH-.514 (CH3 )2 CHO-C2 H5 O- (CH3 )2 CH-.515 (CH3 )2 CHO-CH3 CH2 CH2 O- (CH3 )2 CH-.516 (CH3 )2 CHO- (CH3 )2 CHO- (CH3 )2 CH-.517 (CH3 )2 CHO-C2 H5 CH2 CH2 O- (CH3 )2 CH -518 (CH3 )2 CHO- (CH3 )2 CHCH2 O- (CH3 )2 CH-.519 (CH3 )2 CHO-C2 H5 (CH3 ) CHO- (CH3 )2 CH-.520 (CH3 )2 CHO- (CH3 )3 CO- (CH3 )2 CH-.521 (CH3 )2 CHO-CH3 - (CH3 )3 C-.522 (CH3 )2 CHO-C2 H 5 - (CH3 )3 C-.523 (CH3 )2 CHO-CH3 CH2 CH2 - (CH3 )3 C-.524 (CH3 )2 CHO- (CH3 )2 CH- (CH3 )3 C-.525 (CH3 )2 CHO-C2 H 5 CH2 CH2 - (CH3 )3 C-.526 (CH3 )2 CHO- (CH3 )2 CHCH2 - (CH3 )3 C-.527 (CH3 )2 CHO-C2 H5 (CH3 ) CH- (CH3 )3 C-.528 (CH3 )2 CHO- (CH3 )3 C- ( CH3 )3 C-.529 (CH3 )2 CHO-CFH2 - (CH3 )3 C-.530 (CH3 )2 C HO-CCIH2 - (CH3 )3 C- .531 (CH3 )2 CHO- CF2 H- (CH3 )3 C-. 532 (CH3 )2 CHO- CCI2 H- (CH3 )3 C-.533 (CH3 )2 CHO-CH3 O- (CH3 )3 C-.534 (CH3 )2 CHO-C2 H5 O- (CH3 )3 C-.535 (CH3 )2 CHO CH3 CH2 CH2 0- (CH3)3 C-.536 (CH3)2 CHO (CH3)2 CHO (CH3)3 C-.537 (CH3)2 CHO- C2 H5 CH2 CH2 O- (CH3 )3 C-.538 (CH3 )2 CHO- (CH3 )2 CHCH2 O- (CH3 )3 C-.539 (CH3 )2 CHO C2 H5 (CH3 ) CHO- (CH3 )3 C-.540 (CH3 )2 CHO- (CH3 )3 CO- (CH3 )3 C-.541 (CH3 )2 CHO- CH3 - C3 H 5 .542 (CH3 )2 CHO - C2 H 5 - C3 H 5 - No. RR2 R5 *
.1.543 (CH3)2CHO- CH3CH2CH2- C3H5-.1.543 (CH3 )2 CHOCH3 CH2 CH2 - C3 H5-
.1.544 (CH3)2CHO- (CH3)2CH- C3H5-.1.544 (CH3)2 CHO (CH3)2 CH- C3 H5
.1.545 (CH3)2CHO- C2H5CH2CH2- C3H5-.1.545 (CH3)2 CHO2 C H5CH2 CH2 - C3 H5
.1.546 (CH3)2CHO- (CH3)2CHCH2- C3H5-.1.546 (CH3 )2 CHO- (CH3 )2 CHCH2 - C3 H5-
.1.547 (CH3)2CHO- C2H5(CH3)CH- C3H5-.1.547 (CH3 )2 CHO-C2 H5 (CH3 ) CH- C3 H5-
.1.548 (CH3)2CHO- (CH3)3C- C3H5-.1.548 (CH3 )2 CHO- (CH3 )3 C- C3 H5-
.1.549 (CH3)2CHO- CFH2- C3H5-.1.549 (CH3 )2 CHO- CFH2 - C3 H5-
.1.550 (CH3)2CHO- CCIH2- C3H5-.1.550 (CH3 )2 CHO-CCIH2 - C3 H5-
.1.551 (CH3)2CHO- CF2H- C3H5-.1.551 (CH3 )2 CHO- CF2 H- C3 H5-
.1.552 (CH3)2CHO- CCI2H- C3H5-.1.552 (CH3 )2 CHO- CCI2 H- C3 H5-
.1.553 (CH3)2CHO- CH30- C3H5-.1.553 (CH3 )2 CHOCH3 0- C3 H5-
.1.554 (CH3)2CHO- C2H50- C3H5-.1.554 (CH3 )2 CHO-C2 H5 O- C3 H5-
.1.555 (CH3)2CHO- CH3CH2CH20- C3H5-.1.555 (CH3 )2 CHOCH3 CH2 CH2 O- C3 H5-
.1.556 (CH3)2CHO- (CH3)2CHO- C3H5-.1.556 (CH3)2 CHO (CH3)2 CHOC3 H5
.1.557 (CH3)2CHO- C2H5CH2CH20- C3H5-.1.557 (CH3 )2 CHO-C2 H5 CH2 CH2 O- C3 H5-
.1.558 (CH3)2CHO- (CH3)2CHCH20- C3H5-.1.558 (CH3 )2 CHO- (CH3 )2 CHCH2 O- C3 H5-
.1.559 (CH3)2CHO- C2H5(CH3)CHO- C3H5-.1.559 (CH3 )2 CHO- C2 H5 (CH3 ) CHO- C3 H5-
.1.560 (CH3)2CHO- (CH3)3CO- C3H5-.1.560 (CH3)2 CHO (CH3)3 CO- C3 H5
* R5: C3H5- ist cyclopropyl;* R5 : C3 H5 - is cyclopropyl;
Außerdem sind folgende Benzoylpyrazole der Formel I als Komponente A) geeignet:In addition, the following benzoylpyrazoles of the formula I are suitable as component A):
Tabelle 2: die Verbindungen der Formel 1.2.1 -1.2.560, die sich von den Verbindungen der Formel 1.1 .1 -1.1 bedeutet.Table 2: the compounds of formula 1.2.1 -1.2.560, which is the compounds of formula 1.1 .1 -1.1.
Figure imgf000025_0001
Figure imgf000025_0001
Tabelle 3: die Verbindungen der Formel 1.3.1 -1.3.560, die sich von den Verbindungen der Formel 1.1 .1 -1.1 .560, dadurch unterscheiden, dass R4 HC= CCH2- bedeutet.
Figure imgf000026_0001
Table 3: the compounds of the formula 1.3.1 -1.3.560, which differ from the compounds of the formula 1.1 .1 -1.1 .560, in that R4 denotes HC = CCH2 -.
Figure imgf000026_0001
Tabelle 4: die Verbindungen der Formel 1.4.1-1.4.560, die sich von den Verbindungen der Formel 1.1.1-1.1.560, dadurch unterscheiden, dass R4 HC= CCH2- und R3Table 4: the compounds of the formula 1.4.1-1.4.560, which differ from the compounds of the formula 1.1.1-1.1.560, in that R4 is HC = CCH2 - and R3
CH3CH2SO2- bedeutet.CH3CH2SO2- means.
Figure imgf000026_0002
Figure imgf000026_0002
Tabelle 5: die Verbindungen der Formel 1.5.1-1.5.560, die sich von den Verbindungen der Formel 1.1.1-1.1.560, dadurch unterscheiden, dass R4 CIC= CCH2- bedeutet.Table 5: the compounds of the formula 1.5.1-1.5.560, which differ from the compounds of the formula 1.1.1-1.1.560, in that R4 is CIC = CCH 2 -.
Figure imgf000026_0003
Figure imgf000026_0003
Tabelle 6: die Verbindungen der Formel 1.6.1-1.6.560, die sich von den Verbindungen der Formel 1.1.1-1.1.560, dadurch unterscheiden, dass R4 CIC= CCH2- und R3Table 6: the compounds of the formula 1.6.1-1.6.560, which differ from the compounds of the formula 1.1.1-1.1.560, in that R4 is CIC = CCH2 - and R3
CH3CH2SO2- bedeutet.CH3CH2SO2- means.
Figure imgf000026_0004
Figure imgf000026_0004
Tabelle 7: die Verbindungen der Formel 1.7.1-1.7.560, die sich von den Verbindungen der Formel 1.1.1-1.1.560, dadurch unterscheiden, dass R4 BrC= CCH2- bedeutet.
Figure imgf000027_0001
Table 7: the compounds of the formula 1.7.1-1.7.560, which differ from the compounds of the formula 1.1.1-1.1.560, in that R4 is BrC = CCH 2 -.
Figure imgf000027_0001
Tabelle 8: die Verbindungen der Formel 1.8.1 -1.8.560, die sich von den Verbindungen der Formel 1.1 .1 -1.1 .560, dadurch unterscheiden, dass R4 BrC= CCH2- und R3Table 8: the compounds of the formula 1.8.1 -1.8.560, which differ from the compounds of the formula 1.1 .1 -1.1 .560, in that R4 is BrC = CCH2 - and R3
CH3CH2SO2- bedeutet.CH3CH2SO2- means.
Figure imgf000027_0002
Figure imgf000027_0002
Tabelle 9: die Verbindungen der Formel 1.9.1 -1.9.560, die sich von den Verbindungen der Formel 1.1 .1 -1.1 bedeutet. Table 9: the compounds of formula 1.9.1 -1.9.560, which is the compounds of formula 1.1 .1 -1.1.
Figure imgf000027_0003
Figure imgf000027_0003
Tabelle 10: die Verbindungen der Formel 1.10.1 -1.10.560, die sich von den Verbin- düngen der Formel 1.1 .1 -1.1 .560, dadurch unterscheiden, dass R4 HC= CCHF- und R3 CH3CH2SO2- bedeutet.Table 10: the compounds of the formula 1.10.1 -1.10.560, which differ from the compounds of the formula 1.1 .1 -1.1 .560, in that R4 is HC = CCHF- and R3 is CH3 CH 2 SO 2 -.
O— N O- N
1.10 1.10
S02CH2CH3 Tabelle 11 : die Verbindungen der Formel 1.11.1-1.11.560, die sich von den Verbindungen der Formel 1.1.1-1.1.560, dadurch unterscheiden, dass R4 HC= CCHCI- bedeutet.S02 CH2 CH3 Table 11: the compounds of the formula 1.11.1-1.11.560, which differ from the compounds of the formula 1.1.1-1.1.560, in that R4 denotes HC = CCHCl-.
Figure imgf000028_0001
Figure imgf000028_0001
Tabelle 12: die Verbindungen der Formel 1.12.1-1.12.560, die sich von den Verbindungen der Formel 1.1.1-1.1.560, dadurch unterscheiden, dass R4 HC= CCHCI- und R3 CH3CH2SO2- bedeutet.Table 12: the compounds of the formula 1.12.1-1.12.560, which differ from the compounds of the formula 1.1.1-1.1.560, in that R4 is HC = CCHCl and R3 is CH3 CH 2 SO 2 -.
Figure imgf000028_0002
Figure imgf000028_0002
Tabelle 13: die Verbindungen der Formel 1.13.1-1.13.560, die sich von den Verbindungen der Formel 1.1.1-1.1.560, dadurch unterscheiden, dass R4 HC= CCH(CH3)- bedeutet.Table 13: the compounds of the formula 1.13.1-1.13.560, which differ from the compounds of the formula 1.1.1-1.1.560, in that R4 denotes HC = CCH (CH 3) -.
Figure imgf000028_0003
Figure imgf000028_0003
Tabelle 14: die Verbindungen der Formel 1.14.1-1.14.560, die sich von den Verbindungen der Formel 1.1.1-1.1.560, dadurch unterscheiden, dass R4 HC= CCH(CH3)- und R3 CH3CH2SO2- bedeutet.Table 14: the compounds of formula 1.14.1-1.14.560, which differ from the compounds of formula 1.1.1-1.1.560, in that R4 is HC = CCH (CH 3) - and R3 is CH3 CH 2 SO 2 -.
O— N O- N
1.14 1.14
S02CH2CH3 Tabelle 15: die Verbindungen der Formel 1.15.1 -1.15.560, die sich von den Verbindungen der Formel 1.1 .1 -1.1 .560, dadurch unterscheiden, dass R4 H3C-C= CCH(CH3)- bedeutet.S02 CH2 CH3 Table 15: the compounds of the formula 1.15.1 -1.15.560, which differ from the compounds of the formula 1.1 .1 -1.1 .560, in that R4 is H3 CC = CCH (CH3 ) -.
Figure imgf000029_0001
Figure imgf000029_0001
Tabelle 16: die Verbindungen der Formel 1.16.1 -1.16.560, die sich von den Verbindungen der Formel 1.1 .1 -1.1 .560, dadurch unterscheiden, dass R4 H3C-C= CCH(CH3)- und R3 CH3CH2S02- bedeutet.Table 16: the compounds of formula 1.16.1 -1.16.560, which differ from the compounds of formula 1.1 .1 -1.1 .560, in that R4 H3 CC = CCH (CH3 ) - and R3 CH3 CH2 S02 - means.
Figure imgf000029_0002
Figure imgf000029_0002
Tabelle 17: die Verbindungen der Formel 1.17.1 -1.17.560, die sich von den Verbin- düngen der Fo deutet. Table 17: the compounds of the formula 1.17.1 -1.17.560, which is based on the compounds of the Fo.
Figure imgf000029_0003
Figure imgf000029_0003
Tabelle 18: die Verbindungen der Formel 1.18.1 -1.18.560, die sich von den Verbindungen der Formel 1.1 .1 -1.1 .560, dadurch unterscheiden, dass R6 CH3-und R3 CH3CH2S02- bedeutet.Table 18: the compounds of the formula 1.18.1 -1.18.560, which differ from the compounds of the formula 1.1 .1 -1.1 .560 in that R6 is CH3 and R3 is CH3 CH2 SO2 - ,
O R1 O— NOR1 O-N
1.18 Tabelle 19: die Verbindungen der Formel 1.19.1-1.19.560, die sich von den Verbindungen der Formel 1.1.1-1.1.560, dadurch unterscheiden, dass R6 CH3- und R41.18 Table 19: the compounds of the formula 1.19.1-1.19.560, which differ from the compounds of the formula 1.1.1-1.1.560, in that R6 is CH 3 - and R4
HO CCH2- bedeutet.HO CCH2 - means.
Figure imgf000030_0001
Figure imgf000030_0001
Tabelle 20: die Verbindungen der Formel 1.20.1-1.20.560, die sich von den Verbindungen der Formel 1.1.1-1.1.560, dadurch unterscheiden, dass R6 CH3-, R4 HC= CCH2- und R3 CH3CH2SO2- bedeutet.Table 20: the compounds of the formula 1.20.1-1.20.560, which differ from the compounds of the formula 1.1.1-1.1.560, in that R6 is CH3 -, R4 is HC = CCH2 - and R3 CH3CH2SO2- means.
Figure imgf000030_0002
Figure imgf000030_0002
Tabelle 21 : die Verbindungen der Formel 1.21.1-1.21.560, die sich von den Verbindungen der Formel 1.1.1-1.1.560, dadurch unterscheiden, dass R6 CH3- und R4Table 21: the compounds of the formula 1.21.1-1.21.560, which differ from the compounds of the formula 1.1.1-1.1.560, in that R6 is CH 3 - and R4
CIO CCH2- bedeutet.CIO CCH2 - means.
Figure imgf000030_0003
Figure imgf000030_0003
Tabelle 22: die Verbindungen der Formel 1.22.1-1.22.560, die sich von den Verbindungen der Formel 1.1.1-1.1.560, dadurch unterscheiden, dass R6 CH3-, R4 C\C= CCH2- und R3 CH3CH2SO2- bedeutet.
Figure imgf000031_0001
Table 22: the compounds of formula 1.22.1-1.22.560, which differ from the compounds of formula 1.1.1-1.1.560, in that R6 is CH3 -, R4 C \ C = CCH2 - and R3 is CH3 CH 2 SO 2 -.
Figure imgf000031_0001
Tabelle 23: die Verbindungen der Formel 1.23.1-1.23.560, die sich von den Verbindungen der Formel 1.1.1-1.1.560, dadurch unterscheiden, dass R6 CH3- und R4 BrC= CCH2- bedeutet.Table 23: the compounds of the formula 1.23.1-1.23.560, which differ from the compounds of the formula 1.1.1-1.1.560 in that R6 is CH 3 - and R4 is BrC = CCH 2 -.
Figure imgf000031_0002
Figure imgf000031_0002
Tabelle 24: die Verbindungen der Formel 1.24.1-1.24.560, die sich von den Verbindungen der Formel 1.1.1-1.1.560, dadurch unterscheiden, dass R6 CH3-, R4Table 24: the compounds of the formula 1.24.1-1.24.560, which differ from the compounds of the formula 1.1.1-1.1.560, in that R6 is CH 3 -, R4
BrO CCH2- und R3 CH3CH2SO2- bedeutet.BrO is CCH2 - and R3 is CH3 CH2 SO2 -.
Figure imgf000031_0003
Figure imgf000031_0003
Tabelle 25: die Verbindungen der Formel 1.25.1-1.25.560, die sich von den Verbin düngen der Formel 1.1.1-1.1.560, dadurch unterscheiden, dass R6 CH3- und R4 HC= CCHF- bedeutet.Table 25: the compounds of the formula 1.25.1-1.25.560, which are different from the compounds of the formula 1.1.1-1.1.560, in that R6 is CH 3 - and R4 is HC = CCHF-.
O— N O- N
I.25 I.25
S02CH3 Tabelle 26: die Verbindungen der Formel 1.26.1 -1.26.560, die sich von den Verbindungen der Formel 1.1 .1 -1.1 .560, dadurch unterscheiden, dass R6 CH3-, R4S02 CH3 Table 26: the compounds of the formula 1.26.1 -1.26.560, which differ from the compounds of the formula 1.1 .1 -1.1 .560, in that R6 is CH 3 -, R4
HO CCHF- und R3 CH3CH2SO2- bedeutet.HO is CCHF- and R3 is CH3 CH 2 SO 2 -.
Figure imgf000032_0001
Figure imgf000032_0001
Tabelle 27: die Verbindungen der Formel 1.27.1 -1.27.560, die sich von den Verbindungen der Formel 1.1 .1 -1.1 .560, dadurch unterscheiden, dass R6 CH3- und R4 HC= CCHCI- bedeutet.Table 27: the compounds of the formula 1.27.1 -1.27.560, which differ from the compounds of the formula 1.1 .1 -1.1 .560 in that R6 is CH 3 - and R4 is HC = CCHCl-.
Figure imgf000032_0002
Figure imgf000032_0002
Tabelle 28: die Verbindungen der Formel 1.28.1 -1.28.560, die sich von den Verbindungen der Formel 1.1 .1 -1.1 .560, dadurch unterscheiden, dass R6 CH3-, R4Table 28: the compounds of the formula 1.28.1 -1.28.560, which differ from the compounds of the formula 1.1 .1 -1.1 .560 in that R6 is CH 3 -, R4
HC= CCHCI- und R3 CH3CH2SO2- bedeutet.HC = CCHCl and R3 is CH3 CH 2 SO 2 -.
Figure imgf000032_0003
Figure imgf000032_0003
Tabelle 29: die Verbindungen der Formel 1.29.1 -1.29.560, die sich von den Verbindungen der Formel 1.1 .1 -1.1 .560, dadurch unterscheiden, dass R6 CH3- und R4 HC= CCH(CH3)- bedeutet.Table 29: the compounds of the formula 1.29.1 -1.29.560, which differ from the compounds of the formula 1.1 .1 -1.1 .560 in that R6 is CH3 - and R4 is HC = CCH (CH3 ) - ,
O— N O- N
I.29 I.29
S02CH3 Tabelle 30: die Verbindungen der Formel 1.30.1-1.30.560, die sich von den Verbindungen der Formel 1.1.1-1.1.560, dadurch unterscheiden, dass R6 CH3-, R4S02 CH3 Table 30: the compounds of the formula 1.30.1-1.30.560, which differ from the compounds of the formula 1.1.1-1.1.560, in that R6 is CH 3 -, R4
HO CCH(CHs)- und R3 CH3CH2SO2- bedeutet.HO is CCH (CHs) - and R3 is CH3 CH 2 SO 2 -.
Figure imgf000033_0001
Figure imgf000033_0001
Tabelle 31: die Verbindungen der Formel 1.31.1-1.31.560, die sich von den Verbindungen der Formel 1.1.1-1.1.560, dadurch unterscheiden, dass R6 CH3- und R4 H3C- O CCH(CHs)- bedeutet.Table 31: the compounds of the formula 1.31.1-1.31.560, which differ from the compounds of the formula 1.1.1-1.1.560 in that R6 is CH 3 - and R4 is H 3 C- O CCH (CH 3) - ,
Figure imgf000033_0002
Figure imgf000033_0002
Tabelle 32: die Verbindungen der Formel 1.32.1-1.32.560, die sich von den Verbin düngen der Formel 1.1.1-1.1.560, dadurch unterscheiden, dass R6 CH3-, R4 H3C- O CCH(CH3)- und R3 CH3CH2SO2- bedeutet.Table 32: the compounds of the formula 1.32.1-1.32.560, which are different from the compounds of the formula 1.1.1-1.1.560, in that R6 is CH3 -, R4 is H3 C- O C CH (CH3 ) - and R3 is CH3 CH 2 SO 2 -.
Figure imgf000033_0003
Figure imgf000033_0003
Die Verbindungen der Tabellen 1 bis 32, 1.1.1-1.1.560, 1.2.1-1.2.560, 1.3.1-1.3.560, 1.4.1 I.4.560, 1.5.1-1.5.560, 1.6.1-1.6.560, 1.7.1-1.7.560, 1.8.1-1.8.560, 1.9.1-1.9.560, 1.10.1- 1.10.560, 1.11.1-1.11.560, 1.12.1-1.12.560, 1.13.1-1.13.560, 1.14.1-1.14.560, 1.15.1- 1.15.560, 1.16.1-1.16.560, 1.17.1-1.17.560, 1.18.1-1.18.560, 1.19.1-1.19.560, 1.20.1- I.20.560, 1.21.1-1.21.560, 1.22.1-1.22.560, 1.23.1-1.23.560, 1.24.1-1.24.560, 1.25.1- I.25.560, 1.26.1-1.26.560, 1.27.1-1.27.560, 1.28.1-1.28.560, 1.29.1-1.29.560, 1.30.1- 1.30.560, 1.31.1 -1.31.560 und 1.32.1 -1.32.560 werden im Folgenden abkürzend als Verbindungen 1.1 .1 -1.32.560 bezeichnet.The compounds of Tables 1 to 32, 1.1.1-1.1.560, 1.2.1-1.2.560, 1.3.1-1.3.560, 1.4.1 I.4.560, 1.5.1-1.5.560, 1.6.1 -1.6.560, 1.7.1-1.7.560, 1.8.1-1.8.560, 1.9.1-1.9.560, 1.10.1- 1.10.560, 1.11.1-1.11.560, 1.12.1-1.12 .560, 1.13.1-1.13.560, 1.14.1-1.14.560, 1.15.1- 1.15.560, 1.16.1-1.16.560, 1.17.1-1.17.560, 1.18.1-1.18.560 , 1.19.1-1.19.560, 1.20.1- I.20.560, 1.21.1-1.21.560, 1.22.1-1.22.560, 1.23.1-1.23.560, 1.24.1-1.24.560, 1.25 .1- I.25.560, 1.26.1-1.26.560, 1.27.1-1.27.560, 1.28.1-1.28.560, 1.29.1-1.29.560, 1.30.1- 1.30.560, 1.31.1 -1.31.560 and 1.32.1 -1.32.560 are abbreviated to compounds 1.1 .1 -1.32.560.
In einer besonderen Ausführungsform der Erfindung umfasst die herbizide Mischung als Komponente A) eine herbizid wirksame Menge eines Benzoylpyrazols der Formel I, worin die Variablen folgende Bedeutungen haben:In a particular embodiment of the invention, the herbicidal mixture comprises, as component A), a herbicidally effective amount of a benzoylpyrazole of the formula I in which the variables have the following meanings:
R1 Ci-C4-Alkyl;R1 is C1 -C4 -alkyl;
R2 d-C4-Alkyl;R2 is dC4 alkyl;
R3 Ci-C4-Alkylsulfonyl;R3 is C 1 -C4 -alkylsulfonyl;
R4 Wasserstoff, Cs-Ce-Alkinyl;R4 is hydrogen, Cs-Ce-alkynyl;
R5 Ethyl, Propan-2-yl, Cyclopropyl;R5 is ethyl, propan-2-yl, cyclopropyl;
R6 Wasserstoff; oder dessen landwirtschaftlich geeigneten Salzes.R6 is hydrogen; or its agriculturally suitable salt.
In einer bevorzugten Ausführungsform der Erfindung umfasst die herbizide Mischung als Komponente A) eine herbizid wirksame Menge eines Benzoylpyrazols der Formel I, worin die Variablen folgende Bedeutungen haben:In a preferred embodiment of the invention, the herbicidal mixture comprises, as component A), a herbicidally effective amount of a benzoylpyrazole of the formula I in which the variables have the following meanings:
R1 Methyl;R1 is methyl;
R2 Methyl;R2 is methyl;
R3 Methylsulfonyl;R3 is methylsulfonyl;
R4 Wasserstoff, Prop-2-inyl;R4 is hydrogen, prop-2-ynyl;
R5 Ethyl, Propan-2-yl, Cyclopropyl;R5 is ethyl, propan-2-yl, cyclopropyl;
R6 Wasserstoff; oder dessen landwirtschaftlich geeigneten Salzes.R6 is hydrogen; or its agriculturally suitable salt.
Außerordentlich bevorzugt als Komponent A) der erfindungsgemäßen Mischung ist die Verbindung 1.3.81 , entsprechend der Verbindung der Formel I, worin die Variablen folgende Bedeutungen haben:Exceptionally preferred as component A) of the mixture according to the invention is the compound 1.3.81, corresponding to the compound of the formula I, in which the variables have the following meanings:
R1 Methyl;R1 is methyl;
R2 Methyl;R2 is methyl;
R3 Methylsulfonyl;R3 is methylsulfonyl;
R4 Prop-2-inyl;R4 is prop-2-ynyl;
R5 Ethyl;R5 is ethyl;
R6 Wasserstoff.R6 is hydrogen.
Ebenfalls außerordentlich bevorzugt als Komponent A) der erfindungsgemäßen Mi- schung ist die Verbindung 1.1 .81 entsprechend der Verbindung der Formel I, die Variablen folgende Bedeutungen haben:Likewise highly preferred as component A) of the mixture according to the invention is the compound 1.1.81 corresponding to the compound of the formula I, the variables having the following meanings:
R1 Methyl;R1 is methyl;
R2 Methyl;R2 is methyl;
R3 Methylsulfonyl;R3 is methylsulfonyl;
R4 Wasserstoff;R4 is hydrogen;
R5 Ethyl;R5 is ethyl;
R6 Wasserstoff; oder dessen landwirtschaftlich geeigneten Salzes. Aufgrund ihrer Eigenschaften bevorzugte Benzoylpyrazole der Formel I sind die Verbindungen mit R4 Wasserstoff, insbesondere die Verbindungen 1.3.1 -1.3.560, 1.4.1 - I.4.560, 1.5.1 -1.5.560, 1.6.1 -1.6.560, 1.7.1 -1.7.560, 1.8.1 -1.8.560, 1.9.1 -1.9.560, 1.10.1 - 1.10.560, 1.1 1.1 -1.1 1 .560, 1.12.1 -1.12.560, 1.13.1 -1.13.560, 1.14.1 -1.14.560, 1.15.1 - 1.15.560, 1.16.1 -1.16.560, 1.19.1 -1.19.560, 1.20.1 -1.20.560, 1.21.1 -1.21.560, 1.22.1 - I.22.560, 1.23.1 -1.23.560, 1.24.1 -1.24.560, 1.25.1 -1.25.560, 1.26.1 -1.26.560, 1.27.1 - I.27.560, 1.28.1 -1.28.560, 1.29.1 -1.29.560, 1.30.1 -1.30.560, 1.31.1 -1.31.560, 1.32.1 - I.32.560.R6 is hydrogen; or its agriculturally suitable salt. Benzoylpyrazoles of the formula I which are preferred by virtue of their properties are the compounds where R4 is hydrogen, in particular the compounds 1.3.1 -1.3.560, 1.4.1 - I.4.560, 1.5.1 -1.5.560, 1.6.1 -1.6.560 , 1.7.1 -1.7.560, 1.8.1 -1.8.560, 1.9.1 -1.9.560, 1.10.1 - 1.10.560, 1.1 1.1 -1.1 1 .560, 1.12.1 -1.12.560, 1.13 .1 -1.13.560, 1.14.1 -1.14.560, 1.15.1 - 1.15.560, 1.16.1 -1.16.560, 1.19.1 -1.19.560, 1.20.1 -1.20.560, 1.21.1 -1.21.560, 1.22.1 - I.22.560, 1.23.1 -1.23.560, 1.24.1 -1.24.560, 1.25.1 -1.25.560, 1.26.1 -1.26.560, 1.27.1 - I .27.560, 1.28.1 -1.28.560, 1.29.1 -1.29.560, 1.30.1 -1.30.560, 1.31.1 -1.31.560, 1.32.1 - I.32.560.
Eine besondere Ausführungsform der Erfindung sind Benzoylpyrazole der Formel I, worin die Variablen folgende Bedeutungen haben:A particular embodiment of the invention are benzoylpyrazoles of the formula I in which the variables have the following meanings:
R1 Ci-C4-Alkyl;R1 is C1 -C4 -alkyl;
R2 d-C4-Alkyl;R2 is dC4 alkyl;
R3 Ci-C4-Alkylsulfonyl;R3 is C 1 -C4 -alkylsulfonyl;
R4 Cs-Ce-Alkinyl;R4 is Cs-Ce-alkynyl;
R5 Ethyl, Propan-2-yl, Cyclopropyl;R5 is ethyl, propan-2-yl, cyclopropyl;
R6 Wasserstoff.R6 is hydrogen.
Eine bevorzugte Ausführungsform der Erfindung sind Benzoylpyrazole der Formel I, worin die Variablen folgende Bedeutungen haben:A preferred embodiment of the invention are benzoylpyrazoles of the formula I in which the variables have the following meanings:
R1 Ci-C2-Alkyl;R1 is C1 -C2 -alkyl;
R2 Ci-C2-Alkyl;R2 is C1 -C2 -alkyl;
R3 Ci-C2-Alkylsulfonyl;R3 is C1 -C2 -alkylsulfonyl;
R4 Cs-Ce-Alkinyl;R4 is Cs-Ce-alkynyl;
R5 Ethyl, Propan-2-yl, Cyclopropyl;R5 is ethyl, propan-2-yl, cyclopropyl;
R6 Wasserstoff.R6 is hydrogen.
Außerordentlich bevorzugt ist das Benzoylpyrazol der Formel 1.3.81 , worin die Variablen folgende Bedeutungen haben:Extraordinary preference is given to the benzoylpyrazole of the formula 1.3.81, in which the variables have the following meanings:
R1 Methyl;R1 is methyl;
R2 Methyl;R2 is methyl;
R3 Methylsulfonyl;R3 is methylsulfonyl;
R4 Prop-2-inyl;R4 is prop-2-ynyl;
R5 Ethyl;R5 is ethyl;
R6 Wasserstoff.R6 is hydrogen.
Die Benzoylpyrazole der Formel I sind auf verschiedene Art und Weise erhältlich, beispielsweise nach folgendem Verfahren:The benzoylpyrazoles of the formula I are obtainable in various ways, for example by the following process:
Verfahren A: Umsetzung von Pyrazolen der Formel II (mit R4 = H) mit einer aktivierten Benzoesäure lila oder einer Benzoesäure MIß, die vorzugsweise in situ aktiviert wird, zu dem Acylierungsprodukt der Formel IV und anschließende Umlagerung zu den erfindungsgemäßen Benzoylpyrazolen der Formel I.Method A: Reaction of pyrazoles of the formula II (where R4 = H) with an activated benzoic acid IIIa or a benzoic acid M 1β which preferably activates in situ to the acylation product of the formula IV and subsequent rearrangement to the benzoylpyrazoles of the formula I.
Figure imgf000036_0001
Figure imgf000036_0001
L1 steht für eine nucleophil verdrängbare Abgangsgruppe, wie Halogen, Hetaryl oder Carboxylat. Geeignete Halogengruppen sind beispielsweise Brom und Chlor. Als Heta- rylgruppen kommen beispielsweise Imidazolyl und Pyridyl in Betracht. Beispiele für Carboxylate sind Acetat und Trifluoracetat.L1 represents a nucleophilic displaceable leaving group, such as halogen, hetaryl or carboxylate. Suitable halogen groups are, for example, bromine and chlorine. As hetaryl groups are, for example, imidazolyl and pyridyl into consideration. Examples of carboxylates are acetate and trifluoroacetate.
Die aktivierte Benzoesäure kann direkt eingesetzt werden, wie im Fall der Benzoyl- halogenide oder in situ erzeugt werden, z. B. mit Dicyclohexylcarbodiimid, Triphe- nylphosphan/Azodicarbonsäureester, 2-Pyridindisulfid/Triphenylphosphan, Carbonyl- diimidazol etc.The activated benzoic acid can be used directly, as in the case of benzoyl halides or generated in situ, for. With dicyclohexylcarbodiimide, triphe nylphosphine / azodicarboxylic acid ester, 2-pyridine disulfide / triphenylphosphine, carbonyldiimidazole, etc.
Gegebenenfalls kann es von Vorteil sein, die Acylierungsreaktion in Gegenwart einer Base auszuführen. Die Reaktanden und die Hilfsbase werden dabei zweckmäßiger- weise in äquimolaren Mengen eingesetzt. Ein geringer Überschuß der Hilfsbase, z. B. 1 , 2 bis 1 , 5 Moläquivalente, bezogen auf die Verbindung der Formel II, kann unter Umständen vorteilhaft sein. Optionally, it may be advantageous to carry out the acylation reaction in the presence of a base. The reactants and the auxiliary base are expediently used in equimolar amounts. A slight excess of the auxiliary base, z. B. 1, 2 to 1, 5 molar equivalents, based on the compound of formula II, may be advantageous under certain circumstances.
Als Hilfsbasen eignen sich tertiäre Alkylamine, Pyridin oder Alkalimetallcarbonate. Als Lösungsmittel können beispielsweise chlorierte Kohlenwasserstoffe, wie Methy- lenchlorid, 1 , 2-Dichlorethan, aromatische Kohlenwasserstoffe, wie Toluol, Xylol, Suitable auxiliary bases are tertiary alkylamines, pyridine or alkali metal carbonates. Examples of suitable solvents are chlorinated hydrocarbons, such as methylene chloride, 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene,
Chlorbenzol, Ether, wie Diethylether, Methyl-tert.-butylether, Tetrahydrofuran, Dioxan, Dimethoxyethan, polare aprotische Lösungsmittel, wie Acetonitril, Dimethylformamid, Dimethylsulfoxid oder Ester wie Essigsäureethylester oder Gemische hiervon verwendet werden.Chlorobenzene, ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, dimethoxyethane, polar aprotic solvents such as acetonitrile, dimethylformamide, dimethyl sulfoxide or esters such as ethyl acetate or mixtures thereof may be used.
Werden Benzoylhalogenide als aktivierte Carbonsäurekomponente eingesetzt, so kann es zweckmäßig sein, bei Zugabe dieses Reaktionspartners die Reaktionsmischung auf 0-10°C abzukühlen. Anschließend rührt man bei 20-100°C, vorzugsweise bei 25-50°C, bis die Umsetzung vollständig ist. Die Aufarbeitung erfolgt in üblicher Weise, z. B. wird das Reaktionsgemisch auf Wasser gegossen, das Wertprodukt ext- rahiert. Als Lösungsmittel eignen sich hierfür besonders Methylenchlorid, Diethylether und Essigsäureethylester. If benzoyl halides are used as the activated carboxylic acid component, it may be expedient to cool the reaction mixture to 0-10 ° C. when adding this reaction partner. The mixture is then stirred at 20-100 ° C, preferably at 25-50 ° C until the reaction is complete. The workup is carried out in the usual manner, for. For example, the reaction mixture is poured onto water and the desired product extre- hiert. Particularly suitable solvents for this are methylene chloride, diethyl ether and ethyl acetate.
Nach Trocknen der organischen Phase und Entfernen des Lösungsmittels kann der rohe Ester ohne weitere Reinigung zur Umlagerung eingesetzt werden. After drying the organic phase and removing the solvent, the crude ester can be used without further purification for rearrangement.
Die Umlagerung der Ester zu den Benzoylpyrazolen der Formel I erfolgt zweckmäßi- gerweise bei Temperaturen von 20 bis 40°C in einem Lösungsmittel und in Gegenwart einer Base sowie gegebenenfalls mit Hilfe einer Cyanoverbindung als Katalysator. The rearrangement of the esters to give the benzoylpyrazoles of the formula I is expediently carried out at from 20.degree. To 40.degree. C. in a solvent and in the presence of a base and optionally with the aid of a cyano compound as catalyst.
Als Lösungsmittel können z. B. Acetonitril, Methylenchlorid, 1 , 2-Dichlorethan, Dioxan, Dimethoxyethan, Essigsäureethylester, Toluol oder Gemische hiervon verwendet werden. Bevorzugte Lösungsmittel sind Acetonitril, Dioxan und Dimethoxyethan.As a solvent, for. For example, acetonitrile, methylene chloride, 1, 2-dichloroethane, dioxane, dimethoxyethane, ethyl acetate, toluene or mixtures thereof may be used. Preferred solvents are acetonitrile, dioxane and dimethoxyethane.
Geeignete Basen sind tertiäre Amine wie Triethylamin, Pyridin oder Alkalicarbonate, wie Natriumcarbonat, Kaliumcarbonat, die vorzugsweise in äquimolarer Menge oder bis zu einem vierfachen Überschuß, bezogen auf den Ester, eingesetzt werden. Bevorzugt werden Triethylamin oder Alkalicarbonate verwendet, vorzugsweise in doppelt äquimolaren Verhältnis in Bezug auf den Ester. Suitable bases are tertiary amines such as triethylamine, pyridine or alkali metal carbonates, such as sodium carbonate, potassium carbonate, which are preferably used in an equimolar amount or up to a fourfold excess, based on the ester. Preferably, triethylamine or alkali carbonates are used, preferably in twice equimolar ratio with respect to the ester.
Als Cyanoverbindungen kommen anorganische Cyanide, wie Natriumcyanid, Kali- umcyanid und organische Cyanoverbindungen, wie Acetoncyanhydrin, Trimethylsilycy- anid in Betracht. Sie werden in einer Menge von 1 bis 50 Molprozent, bezogen auf den Ester, eingesetzt. Vorzugsweise werden Acetoncyanhydrin oder Trimethylsilylcyanid, beispielsweise in einer Menge von 5 bis 15, vorzugsweise 10 Molprozent, bezogen auf den Ester, eingesetzt. Suitable cyano compounds are inorganic cyanides, such as sodium cyanide, potassium cyanide and organic cyano compounds, such as acetone cyanohydrin, trimethylsilyl cyanide. They are used in an amount of 1 to 50 mole percent, based on the ester. Preferably, acetone cyanohydrin or trimethylsilyl cyanide, for example in an amount of 5 to 15, preferably 10 mole percent, based on the ester used.
Die Aufarbeitung kann in an sich bekannter Weise erfolgen. Das Reaktionsgemisch wird beispielsweise mit verdünnter Mineralsäure, wie 5 % ige Salzsäure oder Schwe- feisäure, angesäuert, mit einem organischen Lösungsmittel, beispielsweise Methylenchlorid, Essigsäureethylester extrahiert. Der organische Extrakt kann mit 5-10% iger Alkalicarbonatlösung, beispielsweise Natriumcarbonat-, Kaliumcarbonatlösung extrahiert werden. Die wäßrige Phase wird angesäuert und der sich bildende Niederschlag abgesaugt und/oder mit Methylenchlorid oder Essigsäureethylester extrahiert, getrocknet und eingeengt.The workup can be done in a conventional manner. The reaction mixture is treated, for example, with dilute mineral acid, such as 5% hydrochloric acid or sulfuric acid. ferric acid, acidified, extracted with an organic solvent, for example methylene chloride, ethyl acetate. The organic extract can be extracted with 5-10% alkali carbonate solution, for example sodium carbonate, potassium carbonate solution. The aqueous phase is acidified and the precipitate formed is filtered off with suction and / or extracted with methylene chloride or ethyl acetate, dried and concentrated.
Beispiele für die Darstellung von Estern von Hydroxypyrazolen und für die Umlage- rung der Ester sind z. B. in EP-A 282 944 und US 4 643 757 genannt. Examples of the preparation of esters of hydroxypyrazoles and for the rearrangement of the esters are, for. In EP-A 282 944 and US Pat. No. 4,643,757.
Es kann aber auch zweckmäßig sein, den rohen Ester in situ zu erzeugen und die Umlagerungsreaktion ohne Isolierung, Aufreinigung des Esters durchzuführen. However, it may also be expedient to generate the crude ester in situ and to carry out the rearrangement reaction without isolation, purification of the ester.
Verfahren B: Umsetzung von 3- (4, 5-Dihydroisoxazol-5-yl) benzoylpyrazol der Formel I (mit R4 = Wasserstoff) mit einer Verbindung der Formel V:Process B: Reaction of 3- (4, 5-dihydroisoxazol-5-yl) benzoylpyrazole of the formula I (where R4 = hydrogen) with a compound of the formula V:
I mit R4 = WasserstoffI with R4 = hydrogen
I mit R4 + Wasserstoff
Figure imgf000038_0001
I with R4 + hydrogen
Figure imgf000038_0001
L2 steht für eine nucleophil verdrängbare Abgangsgruppe, wie Halogen, z. B. Brom, Chlor, lod, oder Gruppen wie Methylsulfonyl, Toluolsulfonyl. R4 in der Verbindung der Formel V ist Wasserstoff.L2 is a nucleophilically displaceable leaving group, such as halogen, z. For example, bromine, chlorine, iodine, or groups such as methylsulfonyl, toluenesulfonyl. R4 in the compound of formula V is hydrogen.
Die Verbindungen der Formel V können direkt eingesetzt werden, wie z. B. im Fall der Halogene, oder in situ erzeugt werden, z. B. aktivierte Sulfonsäureester (aus dem Alkohol und einem Sulfonsäureanhydrid oder -halogenid). The compounds of formula V can be used directly, such as. B. in the case of halogens, or generated in situ, for. B. activated sulfonic acid esters (from the alcohol and a sulfonic anhydride or halide).
Die Ausgangsverbindungen werden in der Regel im äquimolaren Verhältnis eingesetzt. Es kann aber auch von Vorteil sein, die eine oder andere Komponente im Über- schuß einzusetzen. The starting compounds are usually used in equimolar ratio. However, it can also be advantageous to use one or the other component in excess.
Gegebenenfalls kann es von Vorteil sein, die Umsetzung in Gegenwart einer Base durchzuführen. Die Reaktanden und die Hilfsbase werden dabei zweckmäßigerweise in äquimolaren Mengen eingesetzt. Ein Überschuß der Hilfsbase, z. B. 1 .5 bis 3 Moläquivalente, bezogen auf die Verbindung der Formel II, kann unter Umständen vorteilhaft sein.Optionally, it may be advantageous to carry out the reaction in the presence of a base. The reactants and the auxiliary base are expediently used in equimolar amounts. An excess of the auxiliary base, z. B. 1 .5 to 3 molar equivalents, based on the compound of formula II, may be advantageous under certain circumstances.
Als Hilfsbasen eignen sich tertiäre Alkylamine, wie Triethylamin, Pyridin, Alkalime- tallcarbonate, z. B. Natriumcarbonat, Kaliumcarbonat und Alkalimetallhydride, z. B. Natriumhydrid. Bevorzugt verwendet werden Triethylamin und Pyridin. Suitable auxiliary bases are tertiary alkylamines, such as triethylamine, pyridine, alkali metal carbonates, eg. For example, sodium carbonate, potassium carbonate and alkali metal hydrides, eg. For example, sodium hydride. Preferably used are triethylamine and pyridine.
Als Lösungsmittel kommen z. B. chlorierte Kohlenwasserstoffe, wie Methylenchlorid, 1 , 2-Dichlorethan, aromatische Kohlenwasserstoffe, z. B. Toluol, Xylol, Chlorbenzol, Ether, wie Diethylether, Methyl-tert.-butylether, Tetrahydrofuran, Dioxan, polare aproti- sche Lösungsmittel, wie Acetonitril, Dimethylformamid, Dimethylsulfoxid oder Ester, wie Essigsäureethylester, oder Gemische hiervon in Betracht.As a solvent come z. As chlorinated hydrocarbons such as methylene chloride, 1, 2-dichloroethane, aromatic hydrocarbons, eg. As toluene, xylene, chlorobenzene, ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aprotic solvents such as acetonitrile, dimethylformamide, dimethyl sulfoxide or esters such as ethyl acetate, or mixtures thereof into consideration.
In der Regel liegt die Reaktionstemperatur im Bereich von 0°C bis zur Höhe des Siedepunktes des Reaktionsgemisches. In general, the reaction temperature is in the range of 0 ° C to the height of the boiling point of the reaction mixture.
Die Aufarbeitung kann in an sich bekannter Weise zum Produkt hin erfolgen. Die als Ausgangsmaterialien verwendeten Pyrazole der Formel II (mit R4 = Wasserstoff) sind bekannt oder können nach an sich bekannten Verfahren hergestellt werden (z. B. EP-A 240 001 und J. Prakt. Chem. 315, 383 (1973)).The workup can take place in a manner known per se for the product. The pyrazoles of the formula II (where R4 = hydrogen) used as starting materials are known or can be prepared by processes known per se (for example EP-A 240 001 and J. Prakt. Chem. 315, 383 (1973)). ,
Die Benzoylpyrazole der Formel I und deren landwirtschaftlich geeigneten Salze eig- nen sich - sowohl als Isomerengemische als auch in Form der reinen Isomeren - als Herbizide. Sie eignen sich als solche oder als entsprechend formuliertes Mittel. Die herbiziden Mittel, die die Verbindung I, insbesondere die bevorzugten Ausgestaltungen davon, enthalten, bekämpfen Pflanzenwuchs auf Nichtkulturflächen sehr gut, besonders bei hohen Aufwandmengen. In Kulturen wie Getreide, Reis, Mais, Soja, Baumwol- le, Raps und Zuckerrohr, insbesondere in Mais und Getreide wie Weizen, Roggen,The benzoylpyrazoles of the formula I and their agriculturally suitable salts are suitable as herbicides, both as mixtures of isomers and in the form of pure isomers. They are suitable as such or as appropriately formulated agent. The herbicidal compositions containing the compound I, in particular the preferred embodiments thereof, control plant growth on non-crop surfaces very well, especially at high application rates. In crops such as cereals, rice, maize, soya, cotton, canola and sugarcane, especially in maize and cereals such as wheat, rye,
Hafer, Gerste und Triticale wirken sie gegen Unkräuter und Schadgräser, ohne die Kulturpflanzen nennenswert zu schädigen. Dieser Effekt tritt vor allem bei niedrigen Aufwandmengen auf. Erfindungsgemäß können die Benzoylpyrazole der Formel I als solche und auch als Komponente A) einer herbiziden Mischung enthaltend die Komponenten A) und B) zur Bekämpfung unerwünschten Pflanzenwuchses eingesetzt werden.Oat, barley and triticale, they act against weeds and grass weeds, without damaging the crops significantly. This effect occurs especially at low application rates. According to the invention, the benzoylpyrazoles of the formula I can be used as such and also as component A) of a herbicidal mixture comprising the components A) and B) for controlling undesired plant growth.
Als Komponente B) umfasst die erfindungsgemäße herbizide Mischung eine antidotisch wirksame Menge eines Safeners. Safener sind chemische Verbindungen, die Schaden an Nutzpflanzen verhindern oder reduzieren, ohne die herbizide Wirkung der Benzoylpyrazole der Formel I auf unerwünschte Pflanzen wesentlich zu beeinflussen. Sie können sowohl vor der Aussaat (beispielsweise bei Saatgutbehandlungen, bei Stecklingen oder bei Setzlingen) als auch im Vor- oder Nachauflauf der Nutzpflanze verwendet werden. Die Safener und die Benzoylpyrazole der Formel I können gleich- zeitig oder nacheinander verwendet werden. Geeignete Safener sind beispielsweise (Chinolin-8-oxy)essigsäuren, 1 -Phenyl-5-haloalkyl-1 H-1 ,2,4-triazol-3-carbonsäuren, 1 - Phenyl-4,5-dihydro-5-alkyl-1 H-pyrazol-3,5-dicarbonsäuren, 4,5-Dihydro-5,5-diaryl-3- isoxazolcarbonsäuren, Dichloroacetamide, alpha-Oximinophenylacetonitrile, Ace- tophenonoxime, 4,6-Dihalo-2-phenylpyrimidine, N-[[4-(Aminocarbonyl)phenyl]sulfonyl]- 2-benzoesäureamide, 1 ,8-Naphthalsäureanhydrid, 2-Halo-4-(haloalkyl)-5- thiazolcarbonsäuren, Phosphorthiolate, N-Alkyl-O-phenylcarbamate und 2-Oxo- nicotinsäureamide sowie ihre landwirtschaftlich geeigneten Salze und, vorausgesetzt sie haben eine Säurefunktion, ihre landwirtschaftlich geeigneten Derivate, wie Amide, Ester und Thioester.As component B), the herbicidal mixture according to the invention comprises an antidote effective amount of a safener. Safeners are chemical compounds that prevent or reduce damage to crops without significantly affecting the herbicidal action of Benzoylpyrazole of formula I on undesirable plants. They can be used both before sowing (for example, in seed treatments, cuttings or seedlings) as well as in the pre- or post-emergence of the crop. The safeners and the benzoylpyrazoles of the formula I can be used be used early or in succession. Suitable safeners are, for example, (quinolin-8-oxy) acetic acids, 1-phenyl-5-haloalkyl-1H-1, 2,4-triazole-3-carboxylic acid, 1-phenyl-4,5-dihydro-5-alkyl 1 H-pyrazole-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenone oximes, 4,6-dihalo-2-phenylpyrimidines, N- [ [4- (Aminocarbonyl) phenyl] sulfonyl] -2-benzoic acid amides, 1,8-naphthalic anhydride, 2-halo-4- (haloalkyl) -5-thiazolecarboxylic acids, phosphorothiolates, N-alkyl-O-phenylcarbamates and 2-oxo-nicotinic acid amides and their agriculturally suitable salts and, provided they have an acid function, their agriculturally suitable derivatives such as amides, esters and thioesters.
In einer bevorzugten Ausführungsform der Erfindung ist die Komponente B) der her- biziden Mischung ausgewählt aus der Gruppe der Safener Benoxacor (B1 ), Cloquinto- cet (B2), Cyometrinil (B3), Cyprosulfamid (B4), Dichlormid (B5), Dicyclonon (B6), Dietholat (B7), Fenchlorazol (B8), Fenclorim (B9), Flurazol (B10), Fluxofenim (B1 1 ), Furilazol (B12), Isoxadifen (B13), Mefenpyr (B14), Mephenat (B15), Naphtalinsäurean- hydrid (B16), Oxabetrinil (B17), 4-(Dichloracetyl)-1 -oxa-4-azaspiro[4.5]decanIn a preferred embodiment of the invention, the component B) of the herbicidal mixture is selected from the group of safeners Benoxacor (B1), cloquintocet (B2), cyometrinil (B3), cyprosulfamide (B4), dichloromide (B5), dicyclonone (B6), dietholate (B7), fenchlorazole (B8), fenclorim (B9), flurazole (B10), fluxofenim (B1 1), furilazole (B12), isoxadifen (B13), mefenpyr (B14), mephenate (B15), Naphtalic anhydride (B16), oxabetrinil (B17), 4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane
(MON4660, CAS 71526-07-3) (B18) und 2,2,5-Trimethyl-3-(dichloracetyl)-1 ,3- oxazolidin (R-29148, CAS 52836-31 -4) (B19).(MON4660, CAS 71526-07-3) (B18) and 2,2,5-trimethyl-3- (dichloroacetyl) -1,3-oxazolidine (R-29148, CAS 52836-31 -4) (B19).
Beispiele für erfindungsgemäße Mischungen sind die Mischungen B1.1.1.1 - B19.I.32.560 gemäß Tabelle 33, die als Komponente A) jeweils ein Benzoylpyrazol der Formel I, ausgewählt aus den Tabellen 1 bis 32, dass heißt jeweils eine der Verbindungen 1.1 .1 -1.32.560, und als Komponente B) einen Safener enthalten, ausgewählt aus der Gruppe Benoxacor (B1 ), Cloquintocet (B2), Cyometrinil (B3), Cyprosulfamid (B4), Dichlormid (B5), Dicyclonon (B6), Dietholat (B7), Fenchlorazol (B8), Fenclorim (B9), Flurazol (B10), Fluxofenim (B1 1 ), Furilazol (B12), Isoxadifen (B13), Mefenpyr (B14), Mephenat (B15), Naphtalinsäureanhydrid (B16), Oxabetrinil (B17), 4- (Dichloracetyl)-1 -oxa-4-azaspiro[4.5]decan (MON4660, CAS 71526-07-3) (B18) und 2,2,5-Trimethyl-3-(dichloracetyl)-1 ,3-oxazolidin (R-29148, CAS 52836-31 -4) (B19):Examples of mixtures according to the invention are the mixtures B1.1.1.1 - B19.I.32.560 according to Table 33, which in each case as component A) a benzoylpyrazole of the formula I, selected from Tables 1 to 32, that is in each case one of the compounds 1.1. 1 -1.32.560, and as component B) contain a safener selected from the group Benoxacor (B1), Cloquintocet (B2), Cyometrinil (B3), Cyprosulfamid (B4), dichloromide (B5), dicyclonone (B6), dietholate (B7), fenchlorazole (B8), fenclorim (B9), flurazole (B10), fluxofenim (B1 1), furilazole (B12), isoxadifen (B13), mefenpyr (B14), mephenate (B15), naphthalic anhydride (B16), Oxabetrinil (B17), 4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane (MON4660, CAS 71526-07-3) (B18) and 2,2,5-trimethyl-3- (dichloroacetyl) - 1, 3-oxazolidine (R-29148, CAS 52836-31 -4) (B19):
Tabelle 33: herbizide Mischung Komponente A): Komponente B):Table 33: Herbicidal mixture Component A): Component B):
enthaltend A) und B)containing A) and B)
B1.1.1.1 - B1.I.32.560 1.1.1 -1.32.560 Benoxacor (B1 ) B1.1.1.1 - B1.I.32.560 1.1.1 -1.32.560 Benoxacor (B1)
B2.I.1.1 - B2.I.32.560 1.1.1 -1.32.560 Cloquintocet (B2) B2.I.1.1 - B2.I.32.560 1.1.1 -1.32.560 Cloquintocet (B2)
B3.I.1.1 - B3.I.32.560 1.1.1 -1.32.560 Cyometrinil (B3) B3.I.1.1 - B3.I.32.560 1.1.1 -1.32.560 Cyometrinil (B3)
B4.I.1.1 - B4.I.32.560 1.1.1 -1.32.560 Cyprosulfamid (B4) B4.I.1.1 - B4.I.32.560 1.1.1 -1.32.560 Cyprosulfamide (B4)
B5.I.1.1 - B5.I.32.560 1.1.1 -1.32.560 Dichlormid (B5), B5.I.1.1 - B5.I.32.560 1.1.1 -1.32.560 Dichloride (B5),
B6.I.1.1 - B6.I.32.560 1.1.1 -1.32.560 Dicyclonon (B6), B7.I.1.1 - B7.I.32.560 1.1.1 -1.32.560 Dietholat (B7)B6.I.1.1 - B6.I.32.560 1.1.1 -1.32.560 Dicyclonone (B6), B7.I.1.1 - B7.I.32.560 1.1.1 -1.32.560 Dietholate (B7)
B8.I.1.1 - B8.I.32.560 1.1.1 -1.32.560 Fenchlorazol (B8) B8.I.1.1 - B8.I.32.560 1.1.1 -1.32.560 Fenchlorazole (B8)
B9.I.1.1 - B9.I.32.560 1.1.1 -1.32.560 Fenclorim (B9), B9.I.1.1 - B9.I.32.560 1.1.1 -1.32.560 fenclorim (B9),
B10.I.1.1 - B10.I.32.560 1.1.1 -1.32.560 Flurazol (B10) B10.I.1.1 - B10.I.32.560 1.1.1 -1.32.560 Flurazole (B10)
B1 1 .I.1.1 - B1 1 .1.32.560 1.1.1 -1.32.560 Fluxofenim (B1 1 ) B1 1 .I.1.1 - B1 1 .1.32.560 1.1.1 -1.32.560 Fluxofenim (B1 1)
B12.I.1.1 - B12.I.32.560 1.1.1 -1.32.560 Furilazol (B12) B12.I.1.1 - B12.I.32.560 1.1.1 -1.32.560 Furilazole (B12)
B13.I.1.1 - B13.I.32.560 1.1.1 -1.32.560 Isoxadifen (B13) B13.I.1.1 - B13.I.32.560 1.1.1 -1.32.560 Isoxadifen (B13)
B14.I.1.1 - B14.I.32.560 1.1.1 -1.32.560 Mefenpyr (B14) B14.I.1.1 - B14.I.32.560 1.1.1 -1.32.560 Mefenpyr (B14)
B15.I.1.1 - B15.I.32.560 1.1.1 -1.32.560 Mephenat (B15) B15.I.1.1 - B15.I.32.560 1.1.1 -1.32.560 Mephenate (B15)
B16.I.1.1 - B16.I.32.560 1.1.1 -1.32.560 Naphtalinsäureanhydrid (B16) B16.I.1.1 - B16.I.32.560 1.1.1 -1.32.560 Naphtalic anhydride (B16)
B17.I.1.1 - B17.I.32.560 1.1.1 -1.32.560 Oxabetrinil (B17) B17.I.1.1 - B17.I.32.560 1.1.1 -1.32.560 Oxabetrinil (B17)
B18.I.1.1 - B18.I.32.560 1.1.1 -1.32.560 4-(Dichloracetyl)-1 -oxa-4- azaspiro[4.5]decan (B18) B18.I.1.1 - B18.I.32.560 1.1.1 -1.32.560 4- (Dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane (B18)
B19.I.1.1 - B19.I.32.560 1.1.1 -1.32.560 2,2,5-Trimethyl-3-(dichloracetyl)-1 ,3- oxazolidin (B19) B19.I.1.1 - B19.I.32.560 1.1.1 -1.32.560 2,2,5-Trimethyl-3- (dichloroacetyl) -1,3-oxazolidine (B19)
Die erfindungsgemäßen Mischungen der Tabelle 33, B1.I.1 .1 -B1.I.32.560, B2.I.1 .1 - B2.I.32.560, B3.I.1 .1 -B3.I.32.560, B4.I.1 .1 -B4.I.32.560, B5.I.1 .1 -B5.I.32.560, B6.I.1 .1 - B6.I.32.560, B7.I.1 .1 -B7.I.32.560, B8.I.1 .1 -B8.I.32.560, B9.I.1 .1 -B9.I.32.560, B10.I.1 .1 - B10.I.32.560, B1 1.1.1 .1 -B1 1 .I.32.560, B12.I.1 .1 -B12.I.32.560, B13.I.1 .1 -B13.1.32.560 B14.I.1 .1 -B14.I.32.560, B15.1.1.1 -B15.1.32.560, B16.I.1.1 -B16.I.32.560, B17.I.1.1 - B17.I.32.560, B18.I.1.1 -B18.I.32.560 und B19.I.1.1 -B19.I.32.560 werden im Folgenden abkürzend als Mischungen B1 .1.1 .1 - B19.I.32.560 bezeichnet. Beispiele für bevorzugte erfindungsgemäße Mischungen sind Mischungen, die als Komponente A) jeweils ein Benzoylpyrazol der Formel I, ausgewählt aus den Tabellen 1 bis 32, und als Komponente B) einen Safener enthalten, ausgewählt aus der Gruppe Cloquintocet (B2), Isoxadifen (B13) und Mefenpyr (B14). Beispiele für besonders bevorzugte erfindungsgemäße Mischungen sind Mischungen, die als Komponente A) das Benzoylpyrazol der Formel 1.1.81 , dass heißt die Verbindung der Formel I mitThe mixtures according to the invention of Table 33, B1.I.1.1 -B1.I.32.560, B2.I.1.1 -B2.I.32.560, B3.I.1.1 -B3.I.32.560, B4 .I.1 .1 -B4.I.32.560, B5.I.1 .1 -B5.I.32.560, B6.I.1 .1 - B6.I.32.560, B7.I.1 .1 -B7 .I.32.560, B8.I.1 .1 -B8.I.32.560, B9.I.1 .1 -B9.I.32.560, B10.I.1 .1 - B10.I.32.560, B1 1.1. 1 .1 -B1 1 .I.32.560, B12.I.1 .1 -B12.I.32.560, B13.I.1 .1 -B13.1.32.560 B14.I.1 .1 -B14.I. 32.560, B15.1.1.1 -B15.1.32.560, B16.I.1.1 -B16.I.32.560, B17.I.1.1 - B17.I.32.560, B18.I.1.1 -B18.I.32.560 and B19.I.1.1 -B19.I.32.560 are abbreviated hereafter as mixtures B1 .1.1 .1 - B19.I.32.560. Examples of preferred mixtures according to the invention are mixtures which contain as component A) in each case a benzoylpyrazole of the formula I selected from Tables 1 to 32, and as component B) a safener selected from the group Cloquintocet (B2), isoxadifen (B13) and Mefenpyr (B14). Examples of particularly preferred mixtures according to the invention are mixtures which contain, as component A), the benzoylpyrazole of the formula I.1.81, ie the compound of the formula I ## STR4 ## with
R1 Methyl;R1 is methyl;
R2 Methyl;R2 is methyl;
R3 Methylsulfonyl;R3 is methylsulfonyl;
R4 Wasserstoff;R4 is hydrogen;
R5 Ethyl;R5 is ethyl;
R6 Wasserstoff; oder dessen landwirtschaftlich geeignetes Salz,R6 is hydrogen; or its agriculturally suitable salt,
und als Komponente B) einen Safener enthalten, ausgewählt aus der Gruppe Benoxacor (B1 ), Cloquintocet (B2), Cyometrinil (B3), Cyprosulfamid (B4), Dichlormid (B5), Dicyclonon (B6), Dietholat (B7), Fenchlorazol (B8), Fenclorim (B9), Flurazol (B10), Fluxofenim (B11), Furilazol (B12), Isoxadifen (B13), Mefenpyr (B14), Mephenat (B15), Naphtalinsäureanhydrid (B16), Oxabetrinil (B17), 4-(Dichloracetyl)-1-oxa-4- azaspiro[4.5]decan (B18) und 2,2,5-Trimethyl-3-(dichloracetyl)-1,3-oxazolidin (B19), d.h.die Mischungen B1.I.1.81, B2.1.1.81, B3.1.1.81, B4.I.1.81, B5.I.1.81, B6.I.1.81, B7.I.1.81, B8.I.1.81, B9.1.1.81, B10.1.1.81, B11.1.1.81, B12.1.1.81, B13.1.1.81,and as component B) a safener selected from the group Benoxacor (B1), Cloquintocet (B2), Cyometrinil (B3), Cyprosulfamide (B4), Dichlormid (B5), Dicyclonone (B6), Dietholate (B7), Fenchlorazole ( B8), fenclorim (B9), flurazole (B10), Fluxofenim (B11), Furilazole (B12), Isoxadifen (B13), Mefenpyr (B14), Mephenate (B15), Naphtalic Acid Anhydride (B16), Oxabetrinil (B17), 4- (Dichloroacetyl) -1-oxa-4 azaspiro [4.5] decane (B18) and 2,2,5-trimethyl-3- (dichloroacetyl) -1,3-oxazolidine (B19), ie the mixtures B1.I.1.81, B2.1.1.81, B3.1.1 .81, B4.I.1.81, B5.I.1.81, B6.I.1.81, B7.I.1.81, B8.I.1.81, B9.1.1.81, B10.1.1.81, B11.1.1.81 , B12.1.1.81, B13.1.1.81,
B14.1.1.81, B15.I.1.81, B16.I.1.81, B17.I.1.81, B18.I.1.81 und B19.1.1.81.B14.1.1.81, B15.I.1.81, B16.I.1.81, B17.I.1.81, B18.I.1.81 and B19.1.1.81.
Weitere Beispiele für besonders bevorzugte erfindungsgemäße Mischungen sind Mischungen, die als Komponente A) das Benzoylpyrazol der Formel 1.3.81, dass heißt die Verbindung der Formel I mitFurther examples of particularly preferred mixtures according to the invention are mixtures which contain, as component A), the benzoylpyrazole of the formula 1.3.81, that is to say the compound of the formula I ## STR5 ## with
R1 Methyl;R1 is methyl;
R2 Methyl;R2 is methyl;
R3 Methylsulfonyl;R3 is methylsulfonyl;
R4 Prop-2-inyl;R4 is prop-2-ynyl;
R5 Ethyl;R5 is ethyl;
R6 Wasserstoff;R6 is hydrogen;
und als Komponente B) einen Safener enthalten, ausgewählt aus der Gruppe Benoxacor (B1), Cloquintocet (B2), Cyometrinil (B3), Cyprosulfamid (B4), Dichlormid (B5), Dicyclonon (B6), Dietholat (B7), Fenchlorazol (B8), Fenclorim (B9), Flurazol (B10), Fluxofenim (B11), Furilazol (B12), Isoxadifen (B13), Mefenpyr (B14), Mephenat (B15), Naphtalinsäureanhydrid (B16), Oxabetrinil (B17), 4-(Dichloracetyl)-1-oxa-4- azaspiro[4.5]decan (B18) und 2,2,5-Trimethyl-3-(dichloracetyl)-1,3-oxazolidin (B19), d.h.die Mischungen B1.1.3.81, B2.1.3.81, B3.1.3.81, B4.I.3.81, B5.I.3.81, B6.I.3.81, B7.I.3.81, B8.I.3.81, B9.1.3.81, B10.1.3.81, B11.1.3.81, B12.1.3.81, B13.1.3.81, and as component B) a safener selected from the group Benoxacor (B1), Cloquintocet (B2), Cyometrinil (B3), Cyprosulfamide (B4), Dichlormid (B5), Dicyclonone (B6), Dietholate (B7), Fenchlorazole ( B8), Fenclorim (B9), Flurazole (B10), Fluxofenim (B11), Furilazole (B12), Isoxadifen (B13), Mefenpyr (B14), Mephenate (B15), Naphtalic Acid Anhydride (B16), Oxabetrinil (B17), 4- (Dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane (B18) and 2,2,5-trimethyl-3- (dichloroacetyl) -1,3-oxazolidine (B19), ie mixtures B1.1.3.81 , B2.1.3.81, B3.1.3.81, B4.I.3.81, B5.I.3.81, B6.I.3.81, B7.I.3.81, B8.I.3.81, B9.1.3.81, B10 B.1.3.81, B11.1.3.81, B12.1.3.81, B13.1.3.81,
B14.1.3.81, B15.I.3.81, B16.I.3.81, B17.I.3.81, B18.I.3.81 und B19.I.3.81.B14.1.3.81, B15.I.3.81, B16.I.3.81, B17.I.3.81, B18.I.3.81 and B19.I.3.81.
Beispiele für außerordentlich bevorzugte Mischungen sind die Mischungen, die als Komponente A) die Verbindung 1.1.81 und als Komponente B) einen Safener enthalten, ausgewählt aus der Gruppe Cloquintocet (B2), Isoxadifen (B13) und Mefenpyr (B14), dass heisstdie Mischungen B2.1.1.81, B13.1.1.81 und B14.I.1.81.Examples of extraordinarily preferred mixtures are the mixtures containing as component A) the compound 1.1.81 and as component B) a safener selected from the group Cloquintocet (B2), isoxadifen (B13) and Mefenpyr (B14), ie the mixtures B2.1.1.81, B13.1.1.81 and B14.I.1.81.
Weitere Beispiele für außerordentlich bevorzugte Mischungen sind die Mischungen, die als Komponente A) die Verbindung 1.3.81 und als Komponente B) einen Safener enthält, ausgewählt aus der Gruppe Cloquintocet (B2), Isoxadifen (B13) und Mefenpyr (B14), dass heisst die Mischungen B2.1.3.81, B13.1.3.81 und B14.1.3.81.Further examples of extraordinarily preferred mixtures are the mixtures containing as component A) the compound 1.3.81 and as component B) a safener selected from the group Cloquintocet (B2), isoxadifen (B13) and Mefenpyr (B14), that is the mixtures B2.1.3.81, B13.1.3.81 and B14.1.3.81.
Zur Verbreiterung des Wirkungsspektrums und zur Erzielung synergistischer Effekte können die Benzoylpyrazole der Formel I mit zahlreichen Vertretern anderer herbizider oder wachstumsregulierender Wirkstoffgruppen und/oder mit Safenern gemischt und gemeinsam ausgebracht werden. Beispielsweise kommen als Mischungspartner 1,2,4- Thiadiazole, 1 ,3,4-Thiadiazole, Amide, Aminophosphorsäure und deren Derivate, Ami- notriazole, Anilide, Aryloxy-/Heteroaryloxyalkansäuren und deren Derivate, Benzoesäure und deren Derivate, Benzothiadiazinone, 2-(Hetaroyl/Aroyl)-1 ,3-cyclohexandione, Heteroaryl-Aryl-Ketone, Benzylisoxazolidinone, meta-CF3-Phenylderivate, Carbamate, Chinolincarbonsäure und deren Derivate, Chloracetanilide, Cyclohexenonoximetherde- rivate, Diazine, Dichlorpropionsäure und deren Derivate, Dihydrobenzofurane, Dihydro- furan-3-one, Dinitroaniline, Dinitrophenole, Diphenylether, Dipyridyle, Halogencarbonsäuren und deren Derivate, Harnstoffe, 3-Phenyluracile, Imidazole, Imidazolinone, N- Phenyl-3,4,5,6-tetrahydrophthalimide, Oxadiazole, Oxirane, Phenole, Aryloxy- und He- teroaryloxyphenoxypropionsäureester, Phenylessigsäure und deren Derivate, 2- Phenylpropionsäure und deren Derivate, Pyrazole, Phenylpyrazole, Pyridazine, Pyri- dincarbonsäure und deren Derivate, Pyrimidylether, Sulfonamide, Sulfonylharnstoffe, Triazine, Triazinone, Triazolinone, Triazolcarboxamide, Uracile sowie Phenylpyrazoline und Isoxazoline und deren Derivate in Betracht.To widen the spectrum of action and to achieve synergistic effects, the benzoylpyrazoles of the formula I can be mixed with numerous representatives of other herbicidal or growth-regulating active ingredient groups and / or with safeners and applied together. For example, 1,2,4-thiadiazoles, 1, 3,4-thiadiazoles, amides, aminophosphoric acid and their derivatives, amides, are used as mixing components. notriazoles, anilides, aryloxy / heteroaryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2- (hetaroyl / aroyl) -1, 3-cyclohexanediones, heteroaryl-aryl ketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinolinecarboxylic acid and their derivatives, chloroacetanilides, cyclohexenone oxime ether derivatives, diazines, dichloropropionic acid and derivatives thereof, dihydrobenzofurans, dihydro-furan-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and heteroaryloxyphenoxypropionic acid esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and derivatives thereof, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and their derivatives Derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides, uracils and Ph enylpyrazolines and isoxazolines and their derivatives.
Außerdem kann es von Nutzen sein, die Benzoylpyrazole der Formel I allein oder in Kombination mit anderen Herbiziden oder auch noch mit weiteren Pflanzenschutzmitteln gemischt, gemeinsam auszubringen, beispielsweise mit Mitteln zur Bekämpfung von Schädlingen oder phytopathogenen Pilzen bzw. Bakterien. Von Interesse ist ferner die Mischbarkeit mit Mineralsalzlösungen, welche zur Behebung von Ernährungs- und Spurenelementmängeln eingesetzt werden. Es können auch weitere Additive wie nicht phytotoxische Öle und Ölkonzentrate zugesetzt werden. In addition, it may be useful to use the benzoylpyrazoles of the formula I alone or in combination with other herbicides or mixed with other pesticides, together, for example, with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are used for the elimination of nutritional and trace element deficiencies. Other additives such as non-phytotoxic oils and oil concentrates may also be added.
Beispiele für Herbizide C), die in Kombination mit den Benzoylpyrazolen der Formel I gemäß der vorliegenden Erfindung verwendet werden können, sind: Examples of herbicides C) which can be used in combination with the benzoylpyrazoles of the formula I according to the present invention are:
C1 ) aus der Gruppe der Lipid-Biosynthese-Inhibitoren: C1) from the group of lipid biosynthesis inhibitors:
Alloxydim, Alloxyd im-sodium, Bensulide, Butroxydim, Clethodim, Clodinafop, Clodina- fop-propargyl, Cycloxydim, Cyhalofop, Cyhalofop-butyl, Diclofop, Diclofop-methyl, Fe- noxaprop, Fenoxaprop-ethyl, Fenoxaprop-P, Fenoxaprop-P-ethyl, Fluazifop, Fluazifop- butyl, Fluazifop-P, Fluazifop-P-butyl, Haloxyfop, Haloxyfop-methyl, Haloxyfop-P, Halo- xyfop-P-methyl, Metamifop, Pinoxaden, Profoxydim, Propaquizafop, Quizalofop, Quiza- lofop-ethyl, Quizalofop-tefuryl, Quizalofop-P, Quizalofop-P-ethyl, Quizalofop-P-tefuryl, Sethoxydim, Tepraloxydim, Tralkoxydim, Benfuresat, Butylat, Cycloat, Dalapon, Dime- piperat, EPTC, Esprocarb, Ethofumesat, Flupropanat, Molinat, Orbencarb, Pebulat, Prosulfocarb, TCA, Thiobencarb, Tiocarbazil, Triallate und Vernolat;Alloxydim, alloxide-in-sodium, bensulide, butroxydim, clethodim, clodinafop, clodina-fop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P -ethyl, fluazifop, fluazifopbutyl, fluazifop-P, fluazifop-p-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, halopropyl-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop -ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, benfuresate, butylate, cycloat, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate , Orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;
C2) aus der Gruppe der ALS-Inhibitoren: C2) from the group of ALS inhibitors:
Amidosulfuron, Azimsulfuron, Bensulfuron, Bensulfuron-methyl, Bispyribac, Bispyribac- sodium, Chlorimuron, Chlorimuron-ethyl, Chlorsulfuron, Cinosulfuron, Cloransulam,Amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, bispyribac, bispyribac-sodium, chlorimuron, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, cloransulam,
Cloransulam-methyl, Cyclosulfamuron, Diclosulam, Ethametsulfuron, Ethametsulfuron- methyl, Ethoxysulfuron, Flazasulfuron, Florasulam, Flucarbazone, Flucarbazone- sodium, Flucetosulfuron, Flumetsulam, Flupyrsulfuron, Flupyrsulfuron-methyl-sodium, Foramsulfuron, Halosulfuron, Halosulfuron-methyl, Imazamethabenz, Imazametha- benz-methyl, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, lodosulfuron, lodosulfuron-methyl-sodium, Mesosulfuron, Mesosulfuron-methyl, Meto- sulam, Metsulfuron, Metsulfuron-methyl, Nicosulfuron, Orthosulfamuron, Oxasulfuron, Penoxsulam, Primisulfuron, Primisulfuron-methyl, Propoxycarbazone, Propoxycarba- zone-sodium, Propyrisulfuron, Prosulfuron, Pyrazosulfuron, Pyrazosulfuron-ethyl, Pyri- bambenz-propyl, Pyribenzoxim, Pyrimisulfan, Pyriftalid, Pyriminobac, Pyriminobac- methyl, Pyrithiobac, Pyrithiobac-natrium, Pyroxsulam, Rimsulfuron, Sulfometuron, Sul- fometuron-methyl, Sulfosulfuron, Thiencarbazone, Thiencarbazone-methyl, Thifensul- furon, Thifensulfuron-methyl, Triasulfuron, Tribenuron, Tribenuron-methyl, Trifloxysulfu- ron, Triflusulfuron, Triflusulfuron-methyl und Tritosulfuron;Cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazamethabenz, imazametha- benz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, mesosulfuron, mesosulfuron-methyl, metosulam, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, Penoxsulam, primisulfuron, primisulfuron-methyl, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, pyribambenz-propyl, pyribenzoxime, pyrimisulfan, pyriftalid, pyriminobac, pyrimi- nobimethyl, pyrithiobac, pyrithiobac sodium, Pyroxsulam, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron;
C3) aus der Gruppe der Photosynthese-Inhibitoren: C3) from the group of photosynthesis inhibitors:
Ametryne, Amicarbazon, Atrazin, Bentazon, Bentazon-sodium, Bromacil, Bromofeno- xim, Bromoxynil, Chlorobromuron, Chloridazon, Chlortoluron, Chloroxuron, Cyanazin, Desmedipham, Desmetryn, Dimefuron, Dimethametryn, Diquat, Diquat-dibromid, Diu- ron, Ethidimuron, Fenuron, Fluometuron, Hexazinone, loxynil, Isoproturon, Isouron, Karbutilat, Lenacil, Linuron, Metamitron, Methabenzthiazuron, Metobenzuron, Me- tobromuron, Metoxuron, Metribuzin, Monolinuron, Neburon, Paraquat, Paraquat- dichlorid, Paraquat-dimetilsulfat, Pentanochlor, Phenmedipham, Phenmedipham-ethyl, Prometon, Prometryn, Propanil, Propazin, Pyridafol, Pyridat, Siduron, Simazin, Si- metryn, Tebuthiuron, Terbacil, Terbumeton, Terbuthylazin, Terbutryn, Thidiazuron und Trietazin;Ametryne, amicarbazone, atrazine, bentazone, bentazone-sodium, bromacil, bromofenoxime, bromoxynil, chlorobromuron, chloridazon, chlortoluron, chloroxuron, cyanazine, desmedipham, desmetryn, dimefuron, dimethametryn, diquat, diquat-dibromide, diuron, ethidimuron, Fenuron, fluometuron, hexazinone, loxynil, isoproturon, isourone, carbutilate, lenacil, linuron, metamitron, methabenzthiazuron, metobenzuron, mebromuron, metoxuron, metribuzin, monolinuron, neburon, paraquat, paraquat dichloride, paraquat-dimetilsulfate, pentanochlor, phenmedipham, Phenmedipham-ethyl, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, symmetry, tebuthiuron, terbacil, terbumetone, terbuthylazine, terbutryn, thidiazuron and trietazine;
C4) aus der Gruppe der Protoporphyrinogen-IX-Oxidase-lnhibitoren: C4) from the group of protoporphyrinogen IX oxidase inhibitors:
Acifluorfen, Acifluorfen-natrium, Azafenidin, Bencarbazon, Benzfendizon, Bifenox, Bu- tafenacil, Carfentrazone, Carfentrazone-ethyl, Chlomethoxyfen, Cinidon-ethyl, Fluazo- lat, Flufenpyr, Flufenpyr-ethyl, Flumiclorac, Flumiclorac-pentyl, Flumioxazin, Fluorogly- cofen, Fluoroglycofen-ethyl, Fluthiacet, Fluthiacet-methyl, Fomesafen, Halosafen, Lac- tofen, Oxadiargyl, Oxadiazon, Oxyfluorfen, Pentoxazon, Profluazol, Pyraclonil, Pyraflu- fen, Pyraflufen-ethyl, Saflufenacil, Sulfentrazone, Thidiazimin, 2-Chlor-5-[3,6-dihydro-3- methyl-2,6-dioxo-4-(trifluormethyl)-1 (2H)-pyrimidinyl]-4-fluor-N- [(isopropyl)methylsulfamoyl]benzamid (CAS 372137-35-4), [3-[2-Chlor-4-fluor-5-(1 - methyl-6-trifluormethyl-2,4-dioxo-1 ,2,3,4, -tetrahydropyrimidin-3-yl)phenoxy]-2- pyridyloxy]essigsäureethylester (CAS 353292-31 -6), N-Ethyl-3-(2,6-dichlor-4- trifluormethylphenoxy)-5-methyl-1 H-pyrazol-1 -carboxamid (CAS 452098-92-9), N- Tetrahydrofurfuryl-3-(2,6-dichlor-4-trifluormethylphenoxy)-5-methyl-1 H-pyrazol-1 - carboxamid (CAS 915396-43-9), N-Ethyl-3-(2-chlor-6-fluor-4-trifluormethylphenoxy)-5- methyl-1 H-pyrazol-1 -carboxamid (CAS 452099-05-7) und N-Tetrahydrofurfuryl-3-(2- chlor-6-fluor-4-trifluormethylphenoxy)-5-methyl-1 H-pyrazol-1 -carboxamid (CAS 45100- 03-7);Acifluorfen, acifluorfen sodium, azafenidine, bencarbazone, benzfendizone, bifenox, buafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazine, fluorogly- Fluoroglycofen-ethyl, Fluthiacet, Fluthiacet-methyl, Fomesafen, Halosafen, Lactofen, Oxadiargyl, Oxadiazon, Oxyfluorfen, Pentoxazone, Profluazol, Pyraclonil, Pyrafluene, Pyraflufen-ethyl, Saflufenacil, Sulfentrazone, Thidiazimin, 2-Chloro- 5- [3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl) -1 (2H) -pyrimidinyl] -4-fluoro-N- [(isopropyl) -methylsulfamoyl] -benzamide (CAS 372137- 35-4), [3- [2-chloro-4-fluoro-5- (1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl) -phenoxy ] -2-pyridyloxy] acetic acid ethyl ester (CAS 353292-31 -6), N-ethyl-3- (2,6-dichloro-4-trifluoromethylphenoxy) -5-methyl-1H-pyrazole-1-carboxamide (CAS 452098- 92-9), N-tetrahydrofurfuryl-3- (2,6-dichloro-4-trifluoromethylphenoxy) -5-methyl-1H-pyrazole-1 - carboxamide (CAS 915396-43-9), N-ethyl-3- (2-chloro-6-fluoro-4-trifluoromethylphenoxy) -5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7 ) and N-tetrahydrofurfuryl-3- (2-chloro-6-fluoro-4-trifluoromethylphenoxy) -5-methyl-1H-pyrazole-1-carboxamide (CAS 45100-3-7);
C5) aus der Gruppe der Bleacher-Herbizide: C5) from the group of bleacher herbicides:
Aclonifen, Amitrole, Beflubutamid, Benzobicyclon, Benzofenap, Clomazone, Diflufe- nican, Fluridon, Flurochloridone, Flurtamone, Isoxachlortole, Isoxaflutole, Mesotrione, Norflurazone, Picolinafen, Pyrasulfotole, Pyrazolynat, Pyrazoxyfen, Sulcotrione, Tefu- ryltrione, Tembotrione, Topramezone, 4-Hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6- (trifluormethyl)-3-pyridyl]carbonyl]bicyclo[3.2.1 ]oct-3-en-2-one (CAS 352010-68-5) und 4-(3-Trifluormethylphenoxy)-2-(4-trifluormethylphenyl)pyrimidin (CAS 180608-33-7); C6) aus der Gruppe der EPSP-Synthase-lnhibitoren:Aclonifen, Amitrole, Beflubutamid, Benzobicyclone, Benzofenap, Clomazone, Difluufanican, Fluridone, Flurochloridone, Flurtamone, Isoxachlortole, Isoxaflutole, Mesotrione, Norflurazone, Picolinafen, Pyrasulfotole, Pyrazolynate, Pyrazoxyfen, Sulcotrione, Tefuryltrione, Tembotrione, Topramezone, 4- Hydroxy-3 - [[2 - [(2-methoxyethoxy) methyl] -6- (trifluoromethyl) -3-pyridyl] carbonyl] bicyclo [3.2.1] oct-3-en-2-one (CAS 352010-68- 5) and 4- (3-trifluoromethylphenoxy) -2- (4-trifluoromethylphenyl) pyrimidine (CAS 180608-33-7); C6) from the group of EPSP synthase inhibitors:
Glyphosate, Glyphosate-isopropylammonium und Glyphosate-trimesium (Sulfosate);Glyphosate, glyphosate isopropylammonium and glyphosate trimesium (sulfosates);
C7) aus der Gruppe der Glutamin-Synthase-Inhibitoren:C7) from the group of glutamine synthase inhibitors:
Bilanaphos (Bialaphos), Bilanaphos-natrium, Glufosinate und Glufosinate-ammonium; C8) aus der Gruppe der DHP-Synthase-Inhibitoren: Asulam;Bilanaphos (bialaphos), bilanaphos-sodium, glufosinate and glufosinate-ammonium; C8) from the group of DHP synthase inhibitors: asulam;
C9) aus der Gruppe der Mitose-Inhibitoren: C9) from the group of mitosis inhibitors:
Amiprophos, Amiprophos-methyl, Benfluralin, Butamiphos, Butralin, Carbetamid, Chlorpropham, Chlorthal, Chlorthal-dimethyl, Dinitramin, Dithiopyr, Ethalfluralin, Fluch- loralin, Oryzalin, Pendimethalin, Prodiamin, Propham, Propyzamid, Tebutam, Thiazo- pyr und Trifluralin;Amiprophos, Amiprophos-methyl, Benfluralin, Butamiphos, Butraline, Carbetamide, Chlorpropham, Chlorthal, Chlorthal-dimethyl, Dinitramine, Dithiopyr, Ethalfluralin, Fluroralin, Oryzalin, Pendimethalin, Prodiamine, Propham, Propyzamide, Tebutam, Thiazopyr and Trifluralin;
C10) aus der Gruppe der VLCFA-Inhibitoren: C10) from the group of VLCFA inhibitors:
Acetochlor, Alachlor, Anilofos, Butachlor, Cafenstrole, Dimethachlor, Dimethenamid, Dimethenamid-P, Diphenamid, Fenoxasulfone, Fentrazamide, Flufenacet, Ipfencarba- zone, Mefenacet, Metazachlor, Metolachlor, S-Metolachlor, Naproanilid, Napropamid, Pethoxamid, Piperophos, Pretilachlor, Propachlor, Propisochlor, Pyroxasulfone und Thenylchlor;Acetochlor, Alachlor, Anilofos, Butachlor, Cafenstrole, Dimethachlor, Dimethenamid, Dimethenamid-P, Diphenamid, Fenoxasulfone, Fentrazamide, Flufenacet, Ipflcarba- zone, Mefenacet, Metazachlor, Metolachlor, S-Metolachlor, Naproanilide, Napropamide, Pethoxamide, Piperophos, Pretilachlor, Propachlor, Propisochlor, Pyroxasulfone and Thenylchlorine;
Verbindungen der Formel 2
Figure imgf000045_0001
Compounds of the formula 2
Figure imgf000045_0001
worin die Variablen folgende Bedeutungen haben:wherein the variables have the following meanings:
Y Phenyl oder 5- oder 6-gliedriges Heteroaryl wie eingangs definiert, welche ein- bis dreifach substituiert sein können; R21,R22,R23,R24 H, Halogen, oder Ci-C4-Alkyl; X O oder NH; n 0 oder 1 .Y is phenyl or 5- or 6-membered heteroaryl as defined above, which may be mono- to trisubstituted; R21 , R22 , R23 , R24 are H, halogen, or C 1 -C4 -alkyl; X is O or NH; n 0 or 1.
Verbindu auf:
Figure imgf000045_0002
Connect to:
Figure imgf000045_0002
wobei # die Bindung zu dem Molekülgerüst bedeutet; und where # is the bond to the molecular skeleton; and
R2ii R22R23R24H i C!i F 0der CH3; R25 Halogen, CrC4-Alkyl oder Ci-C4-Haloalkyl; R26 Ci-C4-Alkyl; R27 Halogen, Ci-C4-Alkoxy oder Ci-C4-Haloalkoxy; R28 H, Halogen, Ci-C4- Alkyl, Ci-C4-Haloalkyl oder Ci-C4-Haloalkoxy; m 0, 1 , 2 oder 3; X Sauerstoff;R 2ii R 22R 23R 24H i C! I F 0 of CH3 ; R25 is halogen, C 1 -C4 -alkyl or C 1 -C4 -haloalkyl; R26 is C 1 -C4 -alkyl; R27 is halogen, C 1 -C4 -alkoxy or C 1 -C4 -haloalkoxy; R28 is H, halogen, Ci-C4 - alkyl, Ci-C4 haloalkyl orCi-C4-haloalkoxy; m is 0, 1, 2 or 3; X oxygen;
n 0 oder 1 .n 0 or 1.
Figure imgf000045_0003
Figure imgf000045_0003
R2 H; R22, R23 F; R24 H oder F; X Sauerstoff; n 0 oder 1 .R2 H; R22, R23 F; R24 H or F; X oxygen; n 0 or 1.
Besonders bevorzugte Verbindungen der Formel 2 sind: 3-[5-(2,2-Difluor-ethoxy)-1 -methyl-3-trifluormethyl-1 H-pyrazol-4-ylmethansulfonyl]-4- fluor-5,5-dimethyl-4,5-dihydro-isoxazol (2-1 ); 3-{[5-(2,2-Difluor-ethoxy)-1 -methyl-3-tri- fluormethyl-1 H-pyrazol-4-yl]-fluor-methansulfonyl}-5,5-dimethyl-4,5-dihydro-isoxazol (2- 2); 4-(4-Fluor-5,5-dimethyl-4,5-dihydro-isoxazol-3-sulfonylmethyl)-2-methyl-5- trifluormethyl-2H-[1 ,2,3]triazol (2-3); 4-[(5,5-Dimethyl-4,5-dihydro-isoxazol-3-sulfonyl)- fluor-methyl]-2-methyl-5-trifluormethyl-2H-[1 ,2,3]triazol (2-4); 4-(5,5-Dimethyl-4,5- dihydro-isoxazol-3-sulfonylmethyl)-2-methyl-5-trifluormethyl-2H-[1 ,2,3]triazol (2-5); 3- {[5-(2,2-Difluor-ethoxy)-1 -methyl-3-trifluormethyl-1 H-pyrazol-4-yl]-difluor- methansulfonyl}-5,5-dimethyl-4,5-dihydro-isoxazol (2-6); 4-[(5,5-Dimethyl-4,5-dihydro- isoxazol-3-sulfonyl)-difluor-methyl]-2-methyl-5-trifluormethyl-2H-[1 ,2,3]triazol (2-7); 3- {[5-(2,2-Difluor-ethoxy)-1 -methyl-3-trifluormethyl-1 H-pyrazol-4-yl]-difluor- methansulfonyl}-4-fluor-5,5-dimethyl-4,5-dihydro-isoxazol (2-8); 4-[Difluor-(4-fluor-5,5- dimethyl-4,5-dihydro-isoxazol-3-sulfonyl)-methyl]-2-mParticularly preferred compounds of the formula 2 are: 3- [5- (2,2-Difluoroethoxy) -1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethanesulfonyl] -4-fluoro-5,5-dimethyl-4,5-dihydro-isoxazole (2-1); 3 - {[5- (2,2-Difluoroethoxy) -1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl] -fluoro-methanesulfonyl} -5,5-dimethyl-4,5 dihydro-isoxazole (2- 2); 4- (4-Fluoro-5,5-dimethyl-4,5-dihydroisoxazol-3-sulfonylmethyl) -2-methyl-5-trifluoromethyl-2H- [1,2,3] triazole (2-3); 4 - [(5,5-Dimethyl-4,5-dihydro-isoxazol-3-sulfonyl) -fluoro-methyl] -2-methyl-5-trifluoromethyl-2H- [1,2,3] triazole (2-4 ); 4- (5,5-dimethyl-4,5-dihydroisoxazol-3-sulfonylmethyl) -2-methyl-5-trifluoromethyl-2H- [1,2,3] triazole (2-5); 3- {[5- (2,2-Difluoroethoxy) -1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl] -difluoromethanesulfonyl} -5,5-dimethyl-4,5-dihydro -isoxazole (2-6); 4 - [(5,5-dimethyl-4,5-dihydroisoxazol-3-sulfonyl) -difluoromethyl] -2-methyl-5-trifluoromethyl-2H- [1,2,3] triazole (2-7 ); 3- {[5- (2,2-Difluoroethoxy) -1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl] -difluoromethanesulfonyl} -4-fluoro-5,5-dimethyl-4 , 5-dihydroisoxazole (2-8); 4- [Difluoro (4-fluoro-5,5-dimethyl-4,5-dihydro-isoxazol-3-sulfonyl) -methyl] -2-m
[1 ,2,3]triazol (2-9);[1,2,3] triazole (2-9);
C1 1 ) aus der Gruppe der Cellulose-Biosynthese-Inhibitoren: C1 1) from the group of cellulose biosynthesis inhibitors:
Chlorthiamid, Dichlobenil, Flupoxam und Isoxaben;Chlorthiamide, Dichlobenil, Flupoxam and Isoxaben;
C12) aus der Gruppe der Entkoppler-Herbizide: C12) from the group of decoupling herbicides:
Dinoseb, Dinoterb und DNOC;Dinoseb, Dinoterb and DNOC;
C13) aus der Gruppe der Auxin-Herbizide: C13) from the group of auxin herbicides:
2,4-D, 2,4-DB, Aminopyralid, Aminopyralid-tris(2-hydroxypropyl)ammonium, Benazo- lin, Benazolin-ethyl, Chloramben, Clomeprop, Clopyralid, Dicamba, Dichlorprop, Dich- lorprop-P, Fluroxypyr, Fluroxypyr-butometyl, Fluroxypyr-meptyl, MCPA, MCPA- thioethyl, MCPB, Mecoprop (CMPP), Mecoprop-P (CMPP-P), Picloram, Quinclorac, Quinmerac, TBA (2,3,6), Triclopyr, und 5,6-Dichlor-2-cyclopropyl-4- pyrimidincarbonsäure (CAS 858956-08-8); 2,4-D, 2,4-DB, aminopyralid, aminopyralid-tris (2-hydroxypropyl) ammonium, benazolin, benazolin-ethyl, Chloramben, Clomeprop, Clopyralid, Dicamba, dichlorprop, dichlorprop-P, fluroxypyr, Fluroxypyr-butometyl, fluroxypyr-meptyl, MCPA, MCPA-thioethyl, MCPB, mecoprop (CMPP), mecoprop-P (CMPP-P), picloram, quinclorac, quinmerac, TBA (2,3,6), triclopyr, and 5 6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (CAS 858956-08-8);
C14) aus der Gruppe der Auxin-Transport-Inhibitoren: Diflufenzopyr, Diflufenzopyr- sodium, Naptalam und Naptalam-sodium; C14) from the group of auxin transport inhibitors: diflufenzopyr, diflufenzopyr- none, naptalam and naptalam-sodium;
C15) aus der Gruppe der sonstigen Herbizide: Bromobutid, Chlorflurenol, Chlorflure- nol-methyl, Cinmethylin, Cumyluron, Dalapon, Dazomet, Difenzoquat, Difenzoquat- metilsulfate, Dimethipin, DSMA, Dymron, Endothal, Etobenzanid, Flamprop, Flamprop- isopropyl, Flamprop-methyl Flamprop-M-isopropyl, Flamprop-M-methyl, Flurenol, Flu- renol-butyl, Flurprimidol, Fosamin, Fosamine-ammonium, Indanofan, Maleinsäure- hydrazid, Mefluidid, Metam, Methiozolin, Methylazid, Methylbromid, Methyl-dymron, Methyliodid, MSMA, Ölsäure, Oxaziclomefone, Pelargonsäure, Pyributicarb, Quinocla- min, Triaziflam, Tridiphan und 6-Chlor-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3). C15) from the group of other herbicides: bromobutide, chlorofluorol, chlorofluorol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-methylsulfate, dimethipine, DSMA, dymron, endothal, etobenzanide, flamprop, flampropisopropyl, flamprop -methyl flamprop-M-isopropyl, flamprop-M-methyl, flurenol, fluorenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methiozoline, methyl azide, methyl bromide, methyl dymron, Methyl iodide, MSMA, oleic acid, oxaziclomefones, pelargonic acid, pyributicarb, quinoclamin, triaziflam, tridiphan and 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol (CAS 499223-49-3).
Die Herbizide der Gruppen C1 ) bis C15) können als solche oder in Form ihrer landwirtschaftlich geeigneten Salze oder, vorausgesetzt sie haben eine Säurefunktion, in Form ihrer landwirtschaftlich geeigneten Derivate, wie Amide, Ester und Thioester als Mischungspartner für die Benzoylpyrazole der Formel I verwendet werden. The herbicides of groups C1) to C15) can be used as such or in the form of their agriculturally suitable salts or, provided they have an acid function, in the form of their agriculturally suitable derivatives such as amides, esters and thioesters as mixing partners for the benzoylpyrazoles of the formula I. ,
Die Safener B und die Herbizide C der Gruppen C1 ) bis C15) sind bekannte Wirkstoffe, siehe z. B. The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); B. Hock, C. Fedtke, R. R. Schmidt, Herbizide, Georg Thieme Verlag, Stuttgart 1995. Weitere herbizide Wirkstoffe sind aus WO 96/26202, WO 97/41 1 16, WO 97/41 1 17, WO 97/41 1 18, WO 01/83459 und WO 2008/074991 sowie aus W. Krämer et al. (ed.) "Modern Crop Protection Compounds", Vol. 1 , Wiley VCH, 2007 und der darin zitierten Literatur bekannt.The safeners B and the herbicides C of the groups C1) to C15) are known active ingredients, see, for. B. The Compendium of Pesticide Common Names (Http://www.alanwood.net/pesticides/); B. Hock, C. Fedtke, RR Schmidt, herbicides, Georg Thieme Verlag, Stuttgart 1995. Further herbicidal active ingredients are known from WO 96/26202, WO 97/41 1 16, WO 97/41 1 17, WO 97/41 1 18 WO 01/83459 and WO 2008/074991 and W. Krämer et al. (ed.) "Modern Crop Protection Compounds", Vol. 1, Wiley VCH, 2007 and the literature cited therein.
Als Mischungspartner für die Verbindung der Formel 1.1 .81 bzw. für herbizide Mischungen enthaltend als Komponente A) die Verbindung der Formel 1.1 .81 und als Komponente B) einen Safener sind die oben genannten Herbizide C) besonders ge- eignet, insbesondere die in Tabelle 34 genannten Herbizide c1 bis c150.As the mixing partner for the compound of the formula 1.1 .81 or for herbicidal mixtures containing as component A) the compound of the formula 1.1 .81 and as component B) a safener, the abovementioned herbicides C) are particularly suitable, in particular those in Table 34 mentioned herbicides c1 to c150.
Ebenso als Mischungspartner für die Verbindung der Formel 1.3.81 bzw. für herbizide Mischungen enthaltend als Komponente A) die Verbindung der Formel 1.3.81 und als Komponente B) einen Safener sind die oben genannten Herbizide C) besonders ge- eignet, insbesondere die in Tabelle 34 genannten Herbizide c1 bis c150.Likewise, as a mixing partner for the compound of the formula 1.3.81 or for herbicidal mixtures containing as component A) the compound of the formula 1.3.81 and as component B) a safener are the above-mentioned herbicides C) are particularly suitable, in particular those in Table 34 herbicides c1 to c150.
Beispiele für erfindungsgemäße Mischungen sind die Mischungen c1 .1.1.1 bis c150.L32.560 gemäß Tabelle 34, die als Komponente A) jeweils ein Benzoylpyrazol der Formel I, ausgewählt aus den Tabellen 1 bis 32, dass heißt jeweils eine der Ver- bindungen 1.1.1 -1.32.560, und als Komponente C) ein weiteres Herbizid gemäß Tabelle 34 enthalten:Examples of mixtures according to the invention are the mixtures c1 .1.1.1 to c150.L32.560 according to Table 34, which in each case as component A) a benzoylpyrazole of the formula I, selected from Tables 1 to 32, that is in each case one of the compounds 1.1.1 -1.32.560, and as component C) contain a further herbicide according to Table 34:
Tabelle 34: herbizide Mischung Komponente A): Komponente C)Table 34: herbicidal mixture component A): component C)
enthaltend A) und C) Verbindung I Herbizidcontaining A) and C) compound I herbicide
d .i.1 .1 - d .l.32.560 1.1.1 -1.32.560 c1 : Clethodimd .i.1 .1 - d .l.32.560 1.1.1 -1.32.560 c1: Clethodim
c2.L1 .1 - c2.L32.560 1.1.1 -1.32.560 c2: Clodinafop-propargylc2.L1 .1 - c2.L32.560 1.1.1 -1.32.560 c2: Clodinafop-propargyl
c3.L1 .1 - c3.L32.560 1.1.1 -1.32.560 c3: Cycloxydimc3.L1 .1 - c3.L32.560 1.1.1 -1.32.560 c3: cycloxydim
c4.L1 .1 - c4.L32.560 1.1.1 -1.32.560 c4: Cyhalofop-butylc4.L1 .1 - c4.L32.560 1.1.1 -1.32.560 c4: Cyhalofop-butyl
c5.L1 .1 - c5.L32.560 1.1.1 -1.32.560 c5: Fenoxaprop-P-ethylc5.L1 .1 - c5.L32.560 1.1.1 -1.32.560 c5: fenoxaprop-P-ethyl
c6.L1 .1 - c6.L32.560 1.1.1 -1.32.560 c6: Metamifopc6.L1 .1 - c6.L32.560 1.1.1 -1.32.560 c6: Metamifop
c7.L1 .1 - c7.L32.560 1.1.1 -1.32.560 c7: Diclofop-methylc7.L1 .1 - c7.L32.560 1.1.1 -1.32.560 c7: Diclofop-methyl
c8.L1 .1 - c8.L32.560 1.1.1 -1.32.560 c8: Pinoxadenc8.L1 .1 - c8.L32.560 1.1.1 -1.32.560 c8: Pinoxaden
c9.L1 .1 - c9.L32.560 1.1.1 -1.32.560 c9: Profoxydimc9.L1 .1 - c9.L32.560 1.1.1 -1.32.560 c9: Profoxydim
c10.L1.1 - c10.L32.560 1.1.1 -1.32.560 c10 Sethoxydimc10.L1.1 - c10.L32.560 1.1.1 -1.32.560 c10 Sethoxydim
c1 1.L1.1 - c1 1 .L32.560 1.1.1 -1.32.560 c1 1 Tepraloxydimc1 1.L1.1 - c1 1 .L32.560 1.1.1 -1.32.560 c1 1 Tepraloxydim
c12.L1.1 - c12.L32.560 1.1.1 -1.32.560 c12 Tralkoxydimc12.L1.1 - c12.L32.560 1.1.1 -1.32.560 c12 tralkoximeim
c13.L1.1 - c13.L32.560 1.1.1 -1.32.560 c13 Esprocarbc13.L1.1 - c13.L32.560 1.1.1 -1.32.560 c13 Esprocarb
c14.L1.1 - c14.L32.560 1.1.1 -1.32.560 c14 Ethofumesatec14.L1.1 - c14.L32.560 1.1.1 -1.32.560 c14 Ethofumesate
c15.L1.1 - c15.L32.560 1.1.1 -1.32.560 c15 Pyrasulfotole herbizide Mischung Komponente A): Komponente C)c15.L1.1 - c15.L32.560 1.1.1 -1.32.560 c15 Pyrasulfotole herbicidal mixture component A): component C)
enthaltend A) und C) Verbindung I Herbizidcontaining A) and C) compound I herbicide
c16.L1.1 - c16.L32.560 1.1.1-1.32.560 c16 Prosulfocarbc16.L1.1 - c16.L32.560 1.1.1-1.32.560 c16 Prosulfocarb
c17.L1.1 - c17.L32.560 1.1.1-1.32.560 c17 Thiobencarbc17.L1.1 - c17.L32.560 1.1.1-1.32.560 c17 Thiobencarb
c18.L1.1 - c18.L32.560 1.1.1-1.32.560 c18 Triallatec18.L1.1 - c18.L32.560 1.1.1-1.32.560 c18 Triallates
c19.L1.1 - c19.L32.560 1.1.1-1.32.560 c19 Bensulfuron-methyl c20.L1.1 - c20.L32.560 1.1.1-1.32.560 c20 Bispyribac-sodium c21.L1.1 - c21.L32.560 1.1.1-1.32.560 c21 Cloransulam-methyl c22.L1.1 - c22.L32.560 1.1.1-1.32.560 c22 Chlorsulfuronc19.L1.1 - c19.L32.560 1.1.1-1.32.560 c19 Bensulfuron-methyl c20.L1.1 - c20.L32.560 1.1.1-1.32.560 c20 Bispyribac-sodium c21.L1.1 - c21.L32.560 1.1.1-1.32.560 c21 Cloransulam-methyl c22.L1.1 - c22.L32.560 1.1.1-1.32.560 c22 Chlorosulfuron
c23.L1.1 - c23.L32.560 1.1.1-1.32.560 c23 Chlorimuron-ethyl c24.L1.1 - c24.L32.560 1.1.1-1.32.560 c24 Cyclosulfamuronc23.L1.1 - c23.L32.560 1.1.1-1.32.560 c23 chlorimuron-ethyl c24.L1.1 - c24.L32.560 1.1.1-1.32.560 c24 cyclosulfamuron
c25.L1.1 - c25.L32.560 1.1.1-1.32.560 c25 Orthosulfamuronc25.L1.1 - c25.L32.560 1.1.1-1.32.560 c25 Orthosulfamuron
c26.L1.1 - c26.L32.560 1.1.1-1.32.560 c26 Diclosulamc26.L1.1 - c26.L32.560 1.1.1-1.32.560 c26 diclosulam
c27.L1.1 - c27.L32.560 1.1.1-1.32.560 c27 Florasulamc27.L1.1 - c27.L32.560 1.1.1-1.32.560 c27 Florasulam
c28.L1.1 - c28.L32.560 1.1.1-1.32.560 c28 Flucarbazone-sodium c29.L1.1 - c29.L32.560 1.1.1-1.32.560 c29 Flumetsulamc28.L1.1 - c28.L32.560 1.1.1-1.32.560 c28 Flucarbazone-sodium c29.L1.1 - c29.L32.560 1.1.1-1.32.560 c29 Flumetsulam
c30.L1.1 - c30.L32.560 1.1.1-1.32.560 c30 Flupyrsulfuron-methyl-sodium c31.L1.1 - c31.L32.560 1.1.1-1.32.560 c31 Foramsulfuronc30.L1.1 - c30.L32.560 1.1.1-1.32.560 c30 Flupyrsulfuron-methyl-sodium c31.L1.1 - c31.L32.560 1.1.1-1.32.560 c31 Foramsulfuron
c32.L1.1 - c32.L32.560 1.1.1-1.32.560 c32 I mazamethabenz-methyl c33.L1.1 - c33.L32.560 1.1.1-1.32.560 c33 Imazamoxc32.L1.1 - c32.L32.560 1.1.1-1.32.560 c32 I mazamethabenz-methyl c33.L1.1 - c33.L32.560 1.1.1-1.32.560 c33 imazamox
c34.L1.1 - c34.L32.560 1.1.1-1.32.560 c34 Imazapicc34.L1.1 - c34.L32.560 1.1.1-1.32.560 c34 Imazapic
c35.L1.1 - c35.L32.560 1.1.1-1.32.560 c35 Imazapyrc35.L1.1 - c35.L32.560 1.1.1-1.32.560 c35 Imazapyr
c36.L1.1 - c36.L32.560 1.1.1-1.32.560 c36 Imazaquinc36.L1.1 - c36.L32.560 1.1.1-1.32.560 c36 Imazaquin
c37.L1.1 - c37.L32.560 1.1.1-1.32.560 c37 Imazethapyrc37.L1.1 - c37.L32.560 1.1.1-1.32.560 c37 Imazethapyr
c38.L1.1 - c38.L32.560 1.1.1-1.32.560 c38 Imazosulfuronc38.L1.1 - c38.L32.560 1.1.1-1.32.560 c38 imazosulfuron
c39.L1.1 - c39.L32.560 1.1.1-1.32.560 c39 lodosulfuron-methyl-sodium c40.L1.1 - c40.L32.560 1.1.1-1.32.560 c40 Mesosulfuron-methyl c41.L1.1 - c41.L32.560 1.1.1-1.32.560 c41 Metazosulfuronc39.L1.1 - c39.L32.560 1.1.1-1.32.560 c39 iodosulfuron-methyl-sodium c40.L1.1 - c40.L32.560 1.1.1-1.32.560 c40 mesosulfuron-methyl c41.L1. 1 - c41.L32.560 1.1.1-1.32.560 c41 Metazosulfuron
c42.L1.1 - c42.L32.560 1.1.1-1.32.560 c42 Metsulfuron-methyl c43.L1.1 - c43.L32.560 1.1.1-1.32.560 c43 Metosulamc42.L1.1 - c42.L32.560 1.1.1-1.32.560 c42 Metsulfuron-methyl c43.L1.1 - c43.L32.560 1.1.1-1.32.560 c43 Metosulam
C44.I.1.1 - c44.L32.560 1.1.1-1.32.560 c44 Nicosulfuron C44.I.1.1 - c44.L32.560 1.1.1-1.32.560 c44 Nicosulfuron
c45.L1.1 - c45.L32.560 1.1.1-1.32.560 c45 Penoxsulamc45.L1.1 - c45.L32.560 1.1.1-1.32.560 c45 Penoxsulam
c46.L1.1 - c46.L32.560 1.1.1-1.32.560 c46 Propoxycarbazone-sodiumc46.L1.1 - c46.L32.560 1.1.1-1.32.560 c46 Propoxycarbazone-sodium
C47.I.1.1 - c47.L32.560 1.1.1-1.32.560 c47 Pyrazosulfuron-ethyl c48.L1.1 - c48.L32.560 1.1.1-1.32.560 c48 PyribenzoximC47.I.1.1 - c47.L32.560 1.1.1-1.32.560 c47 Pyrazosulfuron-ethyl c48.L1.1 - c48.L32.560 1.1.1-1.32.560 c48 Pyribenzoxime
c49.L1.1 - c49.L32.560 1.1.1-1.32.560 c49 Pyriftalidc49.L1.1 - c49.L32.560 1.1.1-1.32.560 c49 Pyriftalid
c50.L1.1 - c50.L32.560 1.1.1-1.32.560 c50 Pyroxsulamc50.L1.1 - c50.L32.560 1.1.1-1.32.560 c50 Pyroxsulam
c51.L1.1 - c51.L32.560 1.1.1-1.32.560 c51 Halosulfuron-methyl c52.L1.1 - c52.L32.560 1.1.1-1.32.560 c52 Primisulfuron-methyl c53.L1.1 - c53.L32.560 1.1.1-1.32.560 c53 Rrimsulfuron herbizide Mischung Komponente A): Komponente C) enthaltend A) und C) Verbindung I Herbizidc51.L1.1 - c51.L32.560 1.1.1-1.32.560 c51 halosulfuron-methyl c52.L1.1 - c52.L32.560 1.1.1-1.32.560 c52 primisulfuron-methyl c53.L1.1 - c53.L32.560 1.1.1-1.32.560 c53 rrimsulfuron herbicidal mixture component A): component C) containing A) and C) compound I herbicide
c54.L1.1 - c54.L32.560 1.1.1-1.32.560 c54 Sulfosulfuron c55.L1.1 - c55.L32.560 1.1.1-1.32.560 c55 Thiencarbazone-methyl c56.L1.1 - c56.L32.560 1.1.1-1.32.560 c56 Thifensulfuron-methyl c57.L1.1 - c57.L32.560 1.1.1-1.32.560 c57 Tribenuron-methyl c58.L1.1 - c58.L32.560 1.1.1-1.32.560 c58 Triasulfuronc54.L1.1 - c54.L32.560 1.1.1-1.32.560 c54 sulfosulfuron c55.L1.1 - c55.L32.560 1.1.1-1.32.560 c55 thiencarbazone-methyl c56.L1.1 - c56. L32.560 1.1.1-1.32.560 c56 thifensulfuron-methyl c57.L1.1 - c57.L32.560 1.1.1-1.32.560 c57 tribenuron-methyl c58.L1.1 - c58.L32.560 1.1.1 -1.32.560 c58 triasulfuron
c59.L1.1 - c59.L32.560 1.1.1-1.32.560 c59 Tritosulfuronc59.L1.1 - c59.L32.560 1.1.1-1.32.560 c59 Tritosulfuron
c60.L1.1 - c60.L32.560 1.1.1-1.32.560 c60 Ametrynec60.L1.1 - c60.L32.560 1.1.1-1.32.560 c60 Ametryne
c61.L1.1 - c61.L32.560 1.1.1-1.32.560 c61 Atrazinc61.L1.1 - c61.L32.560 1.1.1-1.32.560 c61 Atrazine
c62.L1.1 - c62.L32.560 1.1.1-1.32.560 c62 Bentazonc62.L1.1 - c62.L32.560 1.1.1-1.32.560 c62 Bentazone
c63.L1.1 - c63.L32.560 1.1.1-1.32.560 c63 Bromoxynilc63.L1.1 - c63.L32.560 1.1.1-1.32.560 c63 Bromoxynil
c64.L1.1 - c64.L32.560 1.1.1-1.32.560 c64 Chlortoluronc64.L1.1 - c64.L32.560 1.1.1-1.32.560 c64 Chlortoluron
c65.L1.1 - c65.L32.560 1.1.1-1.32.560 c65 Diuronc65.L1.1 - c65.L32.560 1.1.1-1.32.560 c65 Diuron
c66.L1.1 - c66.L32.560 1.1.1-1.32.560 c66 Fluometuron c67.L1.1 - c67.L32.560 1.1.1-1.32.560 c67 Hexazinonec66.L1.1 - c66.L32.560 1.1.1-1.32.560 c66 Fluometuron c67.L1.1 - c67.L32.560 1.1.1-1.32.560 c67 Hexazinone
c68.L1.1 - c68.L32.560 1.1.1-1.32.560 c68 loxynilc68.L1.1 - c68.L32.560 1.1.1-1.32.560 c68 loxynil
c69.L1.1 - c69.L32.560 1.1.1-1.32.560 c69 Isoproturonc69.L1.1 - c69.L32.560 1.1.1-1.32.560 c69 isoproturon
c70.L1.1 - c70.L32.560 1.1.1-1.32.560 c70 Pentanochlor c71.L1.1 - c71.L32.560 1.1.1-1.32.560 c71 Linuronc70.L1.1 - c70.L32.560 1.1.1-1.32.560 c70 Pentanochlor c71.L1.1 - c71.L32.560 1.1.1-1.32.560 c71 Linuron
c72.L1.1 - c72.L32.560 1.1.1-1.32.560 c72 Metamitronc72.L1.1 - c72.L32.560 1.1.1-1.32.560 c72 Metamitron
c73.L1.1 - c73.L32.560 1.1.1-1.32.560 c73 Metribuzinc73.L1.1 - c73.L32.560 1.1.1-1.32.560 c73 Metribuzin
C74.I.1.1 - c74.L32.560 1.1.1-1.32.560 c74 Propanil C74.I.1.1 - c74.L32.560 1.1.1-1.32.560 c74 Propanil
c75.L1.1 - c75.L32.560 1.1.1-1.32.560 c75 Pyridatc75.L1.1 - c75.L32.560 1.1.1-1.32.560 c75 pyridate
c76.L1.1 - c76.L32.560 1.1.1-1.32.560 c76 Simazinc76.L1.1 - c76.L32.560 1.1.1-1.32.560 c76 Simazine
c77.L1.1 - c77.L32.560 1.1.1-1.32.560 c77 Terbuthylazin c78.L1.1 - c78.L32.560 1.1.1-1.32.560 c78 Terbutrync77.L1.1 - c77.L32.560 1.1.1-1.32.560 c77 Terbuthylazine c78.L1.1 - c78.L32.560 1.1.1-1.32.560 c78 Terbutryn
c79.L1.1 - c79.L32.560 1.1.1-1.32.560 c79 Paraquat-dichlorid c80.L1.1 - c80.L32.560 1.1.1-1.32.560 c80 CMPP-Pc79.L1.1 - c79.L32.560 1.1.1-1.32.560 c79 Paraquat dichloride c80.L1.1 - c80.L32.560 1.1.1-1.32.560 c80 CMPP-P
c81.L1.1 - c81.L32.560 1.1.1-1.32.560 c81 Butafenacilc81.L1.1 - c81.L32.560 1.1.1-1.32.560 c81 butafenacil
c82.L1.1 - c82.L32.560 1.1.1-1.32.560 c82 Carfentrazone-ethyl c83.L1.1 - c83.L32.560 1.1.1-1.32.560 c83 Flumioxazinc82.L1.1 - c82.L32.560 1.1.1-1.32.560 c82 carfentrazone-ethyl c83.L1.1 - c83.L32.560 1.1.1-1.32.560 c83 flumioxazine
c84.L1.1 - c84.L32.560 1.1.1-1.32.560 c84 Fomesafenc84.L1.1 - c84.L32.560 1.1.1-1.32.560 c84 Fomesafen
c85.L1.1 - c85.L32.560 1.1.1-1.32.560 c85 Oxadiargylc85.L1.1 - c85.L32.560 1.1.1-1.32.560 c85 Oxadiargyl
c86.L1.1 - c86.L32.560 1.1.1-1.32.560 c86 Oxyfluorfenc86.L1.1 - c86.L32.560 1.1.1-1.32.560 c86 Oxyfluorfen
c87.L1.1 - c87.L32.560 1.1.1-1.32.560 c87 Saflufenacilc87.L1.1 - c87.L32.560 1.1.1-1.32.560 c87 Saflufenacil
c88.L1.1 - c88.L32.560 1.1.1-1.32.560 c88 Sulfentrazone herbizide Mischung Komponente A): Komponente C) enthaltend A) und C) Verbindung I Herbizidc88.L1.1 - c88.L32.560 1.1.1-1.32.560 c88 Sulfentrazone herbicidal mixture component A): component C) containing A) and C) compound I herbicide
c89.L1.1 - c89.L32.560 1.1.1-1.32.560 c89: [3-[2-chloro-4-fluoro-5-(1 -methyl-6- trifluoromethyl-2,4-dioxo-1, 2,3,4- tetrahydropyrimidin-3-yl)phenoxy]-2- pyridyloxy]acetat (CAS 353292-31- 6)c89.L1.1 - c89.L32.560 1.1.1-1.32.560 c89: [3- [2-chloro-4-fluoro-5- (1-methyl-6-trifluoromethyl-2,4-dioxo-1 , 2,3,4-tetrahydropyrimidin-3-yl) phenoxy] -2-pyridyloxy] acetate (CAS 353292-31-6)
c90.L1.1 - c90.L32.560 1.1.1-1.32.560 c90: 3-[7-fluoro-3-oxo-4-(prop-2-yn-yl)- 3,4-dihydro-2H-benzo[1,4]-oxazin-6- yl]-1 ,5-dimethyl-6-thi-oxo- [1 ,3,5]triazinan-2,4-dionc90.L1.1 - c90.L32.560 1.1.1-1.32.560 c90: 3- [7-fluoro-3-oxo-4- (prop-2-yn-yl) -3,4-dihydro-2H benzo [1,4] oxazine-6-yl] -1,5-dimethyl-6-thi-oxo [1,3,5] triazinane-2,4-dione
c91.L1.1 - c91.L32.560 1.1.1-1.32.560 c91 : 1 ,5-dimethyl-6-thioxo-3-(2,2,7- trifluoro-3-oxo-4-(prop-2-yn-yl)-3,4- dihydro-2H-benzo[b][1 ,4]-oxazin-6- yl)-1 ,3,5-triazinan-2,4-dion c92.L1.1 - c92.L32.560 1.1.1-1.32.560 c92 Benzobicyclonc91.L1.1 - c91.L32.560 1.1.1-1.32.560 c91: 1, 5-dimethyl-6-thioxo-3- (2,2,7-trifluoro-3-oxo-4- (propyl) 2-yn-yl) -3,4-dihydro-2H-benzo [b] [1,4] oxazin-6-yl) -1,3,5-triazinane-2,4-dione c92.L1.1 - c92.L32.560 1.1.1-1.32.560 c92 Benzobicyclone
c93.L1.1 - c93.L32.560 1.1.1-1.32.560 c93 Clomazonec93.L1.1 - c93.L32.560 1.1.1-1.32.560 c93 Clomazone
c94.L1.1 - c94.L32.560 1.1.1-1.32.560 c94 Diflufenicanc94.L1.1 - c94.L32.560 1.1.1-1.32.560 c94 Diflufenican
c95.L1.1 - c95.L32.560 1.1.1-1.32.560 c95 Flurochloridonec95.L1.1 - c95.L32.560 1.1.1-1.32.560 c95 fluorochloridones
c96.L1.1 - c96.L32.560 1.1.1-1.32.560 c96 Beflubutamidc96.L1.1 - c96.L32.560 1.1.1-1.32.560 c96 Beflubutamide
c97.L1.1 - c97.L32.560 1.1.1-1.32.560 c97 Flurtamonec97.L1.1 - c97.L32.560 1.1.1-1.32.560 c97 Flurtamone
c98.L1.1 - c98.L32.560 1.1.1-1.32.560 c98 Isoxaflutolec98.L1.1 - c98.L32.560 1.1.1-1.32.560 c98 Isoxaflutole
c99.L1.1 - c99.L32.560 1.1.1-1.32.560 c99 Mesotrionec99.L1.1 - c99.L32.560 1.1.1-1.32.560 c99 Mesotrione
c100.1.1.1 - c100.L32.560 1.1.1-1.32.560 c100: Norflurazonec100.1.1.1 - c100.L32.560 1.1.1-1.32.560 c100: Norflurazone
c101.1.1.1 - c101.L32.560 1.1.1-1.32.560 c101 : Picolinafenc101.1.1.1 - c101.L32.560 1.1.1-1.32.560 c101: Picolinafen
c102.1.1.1 - c102.L32.560 1.1.1-1.32.560 c102:Sulcotrionec102.1.1.1 - c102.L32.560 1.1.1-1.32.560 c102: Sulcotrione
c103.1.1.1 - c103.L32.560 1.1.1-1.32.560 c103:Tefuryltrionec103.1.1.1 - c103.L32.560 1.1.1-1.32.560 c103: Tefuryltrione
c104.1.1.1 - c104.L32.560 1.1.1-1.32.560 c104:Tembotrionec104.1.1.1 - c104.L32.560 1.1.1-1.32.560 c104: Tembotrione
C105.I.1.1 - c105.L32.560 1.1.1-1.32.560 c105: Topramezone C105.I.1.1 - c105.L32.560 1.1.1-1.32.560 c105: Toprame zone
C106.I.1.1 - c106.L32.560 1.1.1-1.32.560 c106: Bicyclopyrone C106.I.1.1 - c106.L32.560 1.1.1-1.32.560 c106: Bicyclopyrone
C107.I.1.1 - c107.L32.560 1.1.1-1.32.560 c107:Amitrole C107.I.1.1 - c107.L32.560 1.1.1-1.32.560 c107: Amitrole
C108.I.1.1 - c108.L32.560 1.1.1-1.32.560 c108: Fluometuron C108.I.1.1 - c108.L32.560 1.1.1-1.32.560 c108: Fluometuron
c109.1.1.1 - c109.L32.560 1.1.1-1.32.560 c109:Glyphosatec109.1.1.1 - c109.L32.560 1.1.1-1.32.560 c109: Glyphosate
c110.1.1.1 - c110.L32.560 1.1.1-1.32.560 c110: Glyphosate-isopropylammonium c111.1.1.1 - d 11.1.32.560 1.1.1-1.32.560 c111 : Glyphosate-trimesium (sulfosate) c112.1.1.1 - c112.L32.560 1.1.1-1.32.560 c112: Bialaphosc110.1.1.1 - c110.L32.560 1.1.1-1.32.560 c110: Glyphosate isopropylammonium c111.1.1.1 - d 11.1.32.560 1.1.1-1.32.560 c111: Glyphosate trimesium (sulfosate) c112. 1.1.1 - c112.L32.560 1.1.1-1.32.560 c112: Bialaphos
c113.1.1.1 - c113.L32.560 1.1.1-1.32.560 c113:Glufosinatec113.1.1.1 - c113.L32.560 1.1.1-1.32.560 c113: Glufosinate
c114.1.1.1 - c114.L32.560 1.1.1-1.32.560 c114:Glufosinate-Pc114.1.1.1 - c114.L32.560 1.1.1-1.32.560 c114: Glufosinate-P
c115.1.1.1 - c115.L32.560 1.1.1-1.32.560 c115: Glufosinate-ammoniumc115.1.1.1 - c115.L32.560 1.1.1-1.32.560 c115: glufosinate-ammonium
c116.1.1.1 - c116.L32.560 1.1.1-1.32.560 c116: Pendimethalinc116.1.1.1 - c116.L32.560 1.1.1-1.32.560 c116: pendimethalin
c117.1.1.1 - c117.L32.560 1.1.1-1.32.560 c117: Trifluralin herbizide Mischung Komponente A): Komponente C) enthaltend A) und C) Verbindung I Herbizidc117.1.1.1 - c117.L32.560 1.1.1-1.32.560 c117: trifluralin herbicidal mixture component A): component C) containing A) and C) compound I herbicide
c118.1.1.1 - c118.L32.560 1.1.1-1.32.560 c118:Acetochlorc118.1.1.1 - c118.L32.560 1.1.1-1.32.560 c118: acetochlor
c119.1.1.1 - c119.L32.560 1.1.1-1.32.560 c119:Butachlorc119.1.1.1 - c119.L32.560 1.1.1-1.32.560 c119: Butachlor
c120.1.1.1 - c120.L32.560 1.1.1-1.32.560 c120:Cafenstrolec120.1.1.1 - c120.L32.560 1.1.1-1.32.560 c120: Cafenstrole
c121.1.1.1 - c121.L32.560 1.1.1-1.32.560 c121 : Dimethenamid-Pc121.1.1.1 - c121.L32.560 1.1.1-1.32.560 c121: Dimethenamid-P
c122.1.1.1 - c122.L32.560 1.1.1-1.32.560 c122: Fentrazamidec122.1.1.1 - c122.L32.560 1.1.1-1.32.560 c122: Fentrazamide
c123.1.1.1 - c123.L32.560 1.1.1-1.32.560 c123:Flufenacetc123.1.1.1 - c123.L32.560 1.1.1-1.32.560 c123: Flufenacet
c124.1.1.1 - c124.L32.560 1.1.1-1.32.560 c124:Mefenacetc124.1.1.1 - c124.L32.560 1.1.1-1.32.560 c124: Mefenacet
C125.I.1.1 - c125.L32.560 1.1.1-1.32.560 c125:Metazachlor C125.I.1.1 - c125.L32.560 1.1.1-1.32.560 c125: metazachlor
C126.I.1.1 - c126.L32.560 1.1.1-1.32.560 c126:Metolachlor C126.I.1.1 - c126.L32.560 1.1.1-1.32.560 c126: Metolachlor
C127.I.1.1 - c127.L32.560 1.1.1-1.32.560 c127:S-Metolachlor C127.I.1.1 - c127.L32.560 1.1.1-1.32.560 c127: S-metolachlor
C128.I.1.1 - c128.L32.560 1.1.1-1.32.560 c128: Pethoxamid C128.I.1.1 - c128.L32.560 1.1.1-1.32.560 c128: Pethoxamide
c129.1.1.1 - c129.L32.560 1.1.1-1.32.560 c129:Pretilachlorc129.1.1.1 - c129.L32.560 1.1.1-1.32.560 c129: pretilachlor
c130.1.1.1 - c130.L32.560 1.1.1-1.32.560 c130: Fenoxasulfonec130.1.1.1 - c130.L32.560 1.1.1-1.32.560 c130: fenoxasulfones
c131.1.1.1 - c131.L32.560 1.1.1-1.32.560 c131 : Isoxabenc131.1.1.1 - c131.L32.560 1.1.1-1.32.560 c131: isoxaben
c132.1.1.1 - c132.L32.560 1.1.1-1.32.560 c132: Pyroxasulfonec132.1.1.1 - c132.L32.560 1.1.1-1.32.560 c132: Pyroxasulfones
c133.1.1.1 - c133.L32.560 1.1.1-1.32.560 c133:2,4-Dc133.1.1.1 - c133.L32.560 1.1.1-1.32.560 c133: 2,4-D
c134.1.1.1 - c134.L32.560 1.1.1-1.32.560 c134:Aminopyralidc134.1.1.1 - c134.L32.560 1.1.1-1.32.560 c134: aminopyralid
C135.I.1.1 - c135.L32.560 1.1.1-1.32.560 c135:Clopyralid C135.I.1.1 - c135.L32.560 1.1.1-1.32.560 c135: clopyralid
C136.I.1.1 - c136.L32.560 1.1.1-1.32.560 c136: Dicamba C136.I.1.1 - c136.L32.560 1.1.1-1.32.560 c136: Dicamba
C137.I.1.1 - c137.L32.560 1.1.1-1.32.560 c137: Fluroxypyr-meptyl C137.I.1.1 - c137.L32.560 1.1.1-1.32.560 c137: Fluroxypyr-meptyl
C138.I.1.1 - c138.L32.560 1.1.1-1.32.560 c138:MCPA C138.I.1.1 - c138.L32.560 1.1.1-1.32.560 c138: MCPA
c139.1.1.1 - c139.L32.560 1.1.1-1.32.560 c139:Quincloracc139.1.1.1 - c139.L32.560 1.1.1-1.32.560 c139: Quinclorac
c140.1.1.1 - c140.L32.560 1.1.1-1.32.560 c140:Quinmeracc140.1.1.1 - c140.L32.560 1.1.1-1.32.560 c140: Quinmerac
c141.1.1.1 - c141.L32.560 1.1.1-1.32.560 c141 :Aminocyclopyrachlor c142.1.1.1 - c142.L32.560 1.1.1-1.32.560 c142: Diflufenzopyrc141.1.1.1 - c141.L32.560 1.1.1-1.32.560 c141: Aminocyclopyrachlor c142.1.1.1 - c142.L32.560 1.1.1-1.32.560 c142: Diflufenzopyr
c143.1.1.1 - c143.L32.560 1.1.1-1.32.560 c143: Diflufenzopyr-sodium c144.1.1.1 - c144.L32.560 1.1.1-1.32.560 c144: Dymronc143.1.1.1 - c143.L32.560 1.1.1-1.32.560 c143: Diflufenzopyr-sodium c144.1.1.1 - c144.L32.560 1.1.1-1.32.560 c144: Dymron
C145.I.1.1 - c145.L32.560 1.1.1-1.32.560 c145: Indanofan C145.I.1.1 - c145.L32.560 1.1.1-1.32.560 c145: indanofan
C146.I.1.1 - c146.L32.560 1.1.1-1.32.560 c146: Indaziflam C146.I.1.1 - c146.L32.560 1.1.1-1.32.560 c146: Indaziflam
C147.I.1.1 - c147.L32.560 1.1.1-1.32.560 c147: Oxaziclomefone C147.I.1.1 - c147.L32.560 1.1.1-1.32.560 c147: oxaziclomefones
C148.I.1.1 - c148.L32.560 1.1.1-1.32.560 c148:Triaziflam C148.I.1.1 - c148.L32.560 1.1.1-1.32.560 c148: Triaziflam
c149.1.1.1 - c149.L32.560 1.1.1-1.32.560 c149: Flampropc149.1.1.1 - c149.L32.560 1.1.1-1.32.560 c149: Flamprop
c150.1.1.1 - c150.L32.560 1.1.1-1.32.560 c150: Dichlorprop-pc150.1.1.1 - c150.L32.560 1.1.1-1.32.560 c150: dichloroprop-p
Die erfindungsgemäßen Mischungen der Tabelle 34, werden im Folgenden abkürzend als Mischungen c1.l.1.1-c150.l.32.560 bezeichnet. Beispiele für besonders bevorzugte erfindungsgemäße Mischungen sind Mischungen, die zwei herbizide Wirkstoffe enthalten, nämlich als Komponente A) das Benzo- ylpyrazol der Formel 1.1.81 und als Komponente C) ein weiteres Herbizid C gemäß Tabelle 34, dass heisst die Mischungen d .1.1.81 , c2.l.1.81 , c3.l.1.81 , c4.l.1.81 , c5.L1.81, c6.l-1.81, c7.L1.81, c8.l.1.81 , c9.l.1.81 , c10.l.1.81 , c11.1.1.81 , c12.1.1.81, c13. .1.81, C14.I.1 81, c15. .1.81, C16.I 1.81, c17.L1.81, c18. 1.1.81, c19.L1.81, c20. .1.81, C21.I.1 .81, c22. .1.81, C23.I 1.81, c24.L1.81, c25. 1.1.81, c26.L1.81, c27. .1.81, C28.I.1 .81, c29. .1.81, C30.I 1.81, c31.L1.81, c32. 1.1.81, c33.L1.81, c34. .1.81, C35.I.1 .81, c36. .1.81, C37.I 1.81, c38.L1.81, c39. 1.1.81, c40.L1.81, c41. .1.81, C42.I.1 .81, c43. .1.81, C44.I 1.81, c45.L1.81, 46.I. 1.81, c47.L1.81, c48. .1.81, C49.I.1 .81, c50. .1.81, C51.I 1.81, c52.L1.81, c53. 1.1.81, c54.L1.81, c55. .1.81, C56.I.1 .81, c57. .1.81, C58.I 1.81, c59.L1.81, c60. 1.1.321, c61.1.1.81, c62. .1.81, C63.I.1 81, c64. .1.81, C65.I 1.81, c66.L1.81, c67. 1.1.81, c68.L1.81, c69. .1.81, C70.I.1 81, c71. .1.81, C72.I 1.81, c73.L1.81, c74. 1.1.81, c75.L1.81, c76. .1.81, C77.I.1 81, c78. .1.81, C79.I 1.81, c80.L1.81, c81. 1.1.81, c82.L1.81, c83. .1.81, C84.I.1 81, c85. .1.81, C86.I 1.81, c87.L1.81, c88. 1.1.81, c89.L1.81, c90. .1.81, C91.I.1 81, c92. .1.81, C93.I 1.81, c94.L1.81, c95. 1.1.81, c96.L1.81, c97. .1.81, C98.I.1 .81, c99. .1.81, c100 1.1.81, c101.L1.81, c102.L1.81, 103.1.1.81,The novel mixtures of Table 34 are abbreviated to mixtures c1.l.1.1-c150.l.32.560 hereinafter. Examples of particularly preferred mixtures according to the invention are mixtures which contain two herbicidal active substances, namely, as component A), the benzene ylpyrazole of the formula 1.1.81 and as component C) a further herbicide C according to Table 34, that is the mixtures d .1.1.81, c2.l.1.81, c3.l.1.81, c4.l.1.81, c5.L1 .81, c6.l-1.81, c7.L1.81, c8.l.1.81, c9.l.1.81, c10.l.1.81, c11.1.1.81, c12.1.1.81, c13. .1.81, C14.I.1 81, c15. .1.81, C16.I 1.81, c17.L1.81, c18. 1.1.81, c19.L1.81, c20. .1.81, C21.I.1.81, c22. .1.81, C23.I 1.81, c24.L1.81, c25. 1.1.81, c26.L1.81, c27. .1.81, C28.I.1.81, c29. .1.81, C30.I 1.81, c31.L1.81, c32. 1.1.81, c33.L1.81, c34. .1.81, C35.I.1.81, c36. .1.81, C37.I 1.81, c38.L1.81, c39. 1.1.81, c40.L1.81, c41. .1.81, C42.I.1.81, c43. .1.81, C44.I 1.81, c45.L1.81, 46.I. 1.81, c47.L1.81, c48. .1.81, C49.I.1.81, c50. .1.81, C51.I 1.81, c52.L1.81, c53. 1.1.81, c54.L1.81, c55. .1.81, C56.I.1.81, c57. .1.81, C58.I 1.81, c59.L1.81, c60. 1.1.321, c61.1.1.81, c62. .1.81, C63.I.1 81, c64. .1.81, C65.I 1.81, c66.L1.81, c67. 1.1.81, c68.L1.81, c69. .1.81, C70.I.1 81, c71. .1.81, C72.I 1.81, c73.L1.81, c74. 1.1.81, c75.L1.81, c76. .1.81, C77.I.1 81, c78. .1.81, C79.I 1.81, c80.L1.81, c81. 1.1.81, c82.L1.81, c83. .1.81, C84.I.1 81, c85. .1.81, C86.I 1.81, c87.L1.81, c88. 1.1.81, c89.L1.81, c90. .1.81, C91.I.1 81, c92. .1.81, C93.I 1.81, c94.L1.81, c95. 1.1.81, c96.L1.81, c97. .1.81, C98.I.1.81, c99. .1.81, c100 1.1.81, c101.L1.81, c102.L1.81, 103.1.1.81,
104. .1.81, 105.1.1 .81, c106.L1.81, c107l.1.81, c108.1.1.81, c109.L1.81, c110.1.1.81 , c111.1.1.81 , d 12.1.1.81 , d 13.1.1.81 , c114.1.1.81 , c115.1.1.81 , d 16.1.1.81 , c117.1.1.81 c118.1.1.81 , c119.1.1.81 , C120.I.1.81 , c121.1.1.81 , C122.I.1.81 , C123.I.1.81 , C124.I.1.81 c125.L1.81, c126.L1.81, C127.I.1.81, c128.l.1.81, c129.l.1.81, C130.I.1.81 , c131.1.1.81 c132.L1.81, c133.L1.81, c134.1.1.81, C135.I.1.81 , C136.I.1.81 , C137.I.1.81, C138.I.1.81 c139.L1.81, c140.L1.81, c141.1.1.81, C142.I.1.81 , C143.I.1.81 , C144.I.1.81, C145.I.1.81 c146.L1.81, c147.L1.81, c148.l.1.81, C149.I.1.81 , C150.I.1.81.104. .1.81, 105.1.1 .81, c106.L1.81, c107.1.81, c108.1.1.81, c109.L1.81, c110.1.1.81, c111.1.1.81, d.12.1.1.81, d 13.1.1.81, c114.1.1.81, c115.1.1.81, d 16.1.1.81, c117.1.1.81 c118.1.1.81, c119.1.1.81, C120.I.1.81, c121.1.1.81 , C122.I.1.81, C123.I.1.81, C124.I.1.81 c125.L1.81, c126.L1.81, C127.I.1.81, c128.l.1.81, c129.l.1.81, C130. I.1.81, C131.1.1.81 C132.L1.81, C133.L1.81, C134.1.1.81, C135.I.1.81, C136.I.1.81, C137.I.1.81, C138.I.1.81 c139.L1.81, c140.L1.81, c141.1.1.81, C142.I.1.81, C143.I.1.81, C144.I.1.81, C145.I.1.81 c146.L1.81, c147.L1 .81, c148.l.1.81, C149.I.1.81, C150.I.1.81.
Weitere Beispiele für besonders bevorzugte erfindungsgemäße Mischungen sind Mischungen, die zwei herbizide Wirkstoffe enthalten, nämlich als Komponente A) das Benzoylpyrazol der Formel 1.3.81 und als Komponente C) ein weiteres Herbizid C gemäß Tabelle 34, dass heisst die Mischungen d .1.3.81 , c2.1.3.81 , c3.1.3.81 , c4.1.3.81 , c5.l. 3.81, c6.L3.81, c7.L3.81 , c8.L3.81 , c9.1.3.81 , c10.1.3.81, d 1.1.3.81 , c12.l.3.81 , c13. 1.3.81, c14. .3.81, C15.I 3.81, C16.I .3.81, c17.L3.81, c18.L3.81, c19.L3.81, c20. 1.3.81, c21. .3.81, C22.I 3.81, C23.I .3.81, c24.L3.81, c25.L3.81, c26.L3.81, c27. 1.3.81, c28. .3.81, C29.I 3.81, C30.I .3.81, c31.1.3.81, c32.L3.81, c33.L3.81, c34. 1.3.81, c35. .3.81, C36.I 3.81, C37.I .3.81, c38.L3.81, c39.L3.81, c40.L3.81, c41. 1.3.81, c42. .3.81, C43.I 3.81, C44.I .3.81, c45.L3.81, c46.L3.81, c47.l.3.81, c48. 1.3.81, c49. .3.81, C50.I 3.81, C51.I .3.81, c52.1.3.81, c53.1.3.81, c54.L3.81, c55. 1.3.81, c56. .3.81, C57.I 3.81, C58.I .3.81, c59.L3.81, c60.L3.321, c61.1.3.81, c62. 1.3.81, c63. .3.81, C64.I 3.81, C65.I .3.81, c66.L3.81, c67.L3.81, c68.L3.81, c69. 1.3.81, c70. .3.81, C71.I 3.81, C72.I .3.81, c73.L3.81, c74.L3.81, c75.L3.81, c76. 1.3.81, c77. .3.81, C78.I 3.81, C79.I .3.81, c80.L3.81, c81.1.3.81, c82.L3.81, c83. 1.3.81, c84. .3.81, C85.I 3.81, C86.I .3.81, c87.L3.81, c88.L3.81, c89.L3.81, c90. 1.3.81, c91. .3.81, C92.I 3.81, C93.I .3.81, c94.1.3.81, c95.L3.81, c96.L3.81, c97. 1.3.81, c98. .3.81, C99.I 3.81, c100 .1.3.81, c101.1.3.81, c102.L3.81, 103.1.3.81, 104.1.3.81 , 105.1.3.81 , c106.l.3.81 , c107.L3.81 , c108.L3.81 , c109.L3.81 , c1 10.l.3.81 , c1 1 1.1.3.81 , c1 12.1.3.81 , c1 13.1.3.81 , d 14.1.3.81 , c1 15.1.3.81 , d 16.1.3.81 , c1 17.1.3.81 c1 18.1.3.81 , c1 19.1.3.81 , c120.l.3.81 , c121 .1.3.81 , C122.I.3.81 , c123.L3.81 , c124.1.3.81 C125.I.3.81 , c126.L3.81 , c127.L3.81 , c128.l.3.81 , c129.l.3.81 , c130.l.3.81 , c131 .1.3.81 C132.I.3.81 , c133.1.3.81 , C134.I.3.81 , c135.L3.81 , c136.L3.81 , c137.L3.81 , c138.L3.81 C139.I.3.81 , c140.L3.81 , c141.1.3.81 , c142.1.3.81 , c143.l.3.81 , c144.l.3.81 , c145.l.3.81 c146.L3.81 , c147.L3.81 , c148.l.3.81 , c149.l.3.81 , d 50.1.3.81 .Further examples of particularly preferred mixtures according to the invention are mixtures which contain two herbicidal active compounds, namely as component A) the benzoylpyrazole of the formula 1.3.81 and as component C) a further herbicide C according to Table 34, that is to say the mixtures d .1.3.81 , c2.1.3.81, c3.1.3.81, c4.1.3.81, c5.l. 3.81, c6.L3.81, c7.L3.81, c8.L3.81, c9.1.3.81, c10.1.3.81, d 1.1.3.81, c12.l.3.81, c13. 1.3.81, c14. .3.81, C15.I 3.81, C16.I.3.81, c17.L3.81, c18.L3.81, c19.L3.81, c20. 1.3.81, c21. .3.81, C22.I 3.81, C23.I.3.81, c24.L3.81, c25.L3.81, c26.L3.81, c27. 1.3.81, c28. .3.81, C29.I 3.81, C30.I.3.81, c31.1.3.81, c32.L3.81, c33.L3.81, c34. 1.3.81, c35. .3.81, C36.I 3.81, C37.I.3.81, c38.L3.81, c39.L3.81, c40.L3.81, c41. 1.3.81, c42. .3.81, C43.I 3.81, C44.I.3.81, c45.L3.81, c46.L3.81, c47.l.3.81, c48. 1.3.81, c49. .3.81, C50.I 3.81, C51.I.3.81, c52.1.3.81, c53.1.3.81, c54.L3.81, c55. 1.3.81, c56. .3.81, C57.I 3.81, C58.I.3.81, c59.L3.81, c60.L3.321, c61.1.3.81, c62. 1.3.81, c63. .3.81, C64.I 3.81, C65.I.3.81, c66.L3.81, c67.L3.81, c68.L3.81, c69. 1.3.81, c70. .3.81, C71.I 3.81, C72.I.3.81, c73.L3.81, c74.L3.81, c75.L3.81, c76. 1.3.81, c77. .3.81, C78.I 3.81, C79.I.3.81, c80.L3.81, c81.1.3.81, c82.L3.81, c83. 1.3.81, c84. .3.81, C85.I 3.81, C86.I.3.81, c87.L3.81, c88.L3.81, c89.L3.81, c90. 1.3.81, c91. .3.81, C92.I 3.81, C93.I.3.81, c94.1.3.81, c95.L3.81, c96.L3.81, c97. 1.3.81, c98. .3.81, C99.I 3.81, c100.1.3.81, c101.1.3.81, c102.L3.81, 103.1.3.81, 104.1.3.81, 105.1.3.81, c106.l.3.81, c107.L3.81, c108.L3.81, c109.L3.81, c1 10.l.3.81, c1 1 1.1.3.81, c1 12.1.3.81, c1 13.1.3.81, d 14.1.3.81, c1 15.1.3.81, d 16.1.3.81, c1 17.1.3.81 c1 18.1.3.81, c1 19.1.3.81, c120.l.3.81, c121 .1.3.81, C122.I. 3.81, c123.L3.81, c124.1.3.81 C125.I.3.81, c126.L3.81, c127.L3.81, c128.l.3.81, c129.l.3.81, c130.l.3.81, c131 .1.3.81 C132.I.3.81, c133.1.3.81, C134.I.3.81, c135.L3.81, c136.L3.81, c137.L3.81, c138.L3.81 C139.I.3.81 , c140.L3.81, c141.1.3.81, c142.1.3.81, c143.l.3.81, c144.l.3.81, c145.l.3.81 c146.L3.81, c147.L3.81, c148. l.3.81, c149.l.3.81, d 50.1.3.81.
Ganz besonders bevorzugt sind Mischungen gemäß der folgenden Tabelle 35, enthaltend als Komponente A) die Verbindung der Formel 1.3.81 , dass heißt das Benzoyl- pyrazol der Formel I mitVery particular preference is given to mixtures according to the following Table 35, containing as component A) the compound of the formula 1.3.81, that is to say the benzoylpyrazole of the formula I ## STR4 ## with
R1 Methyl;R1 is methyl;
R2 Methyl;R2 is methyl;
R3 Methylsulfonyl;R3 is methylsulfonyl;
R4 Prop-2-inyl;R4 is prop-2-ynyl;
R5 Ethyl;R5 is ethyl;
R6 Wasserstoff;R6 is hydrogen;
und zwei weitere Herbizide C, Ca und Cb, ausgewählt aus den Herbiziden gemäß Tabelle 34, c1 -c150:and two further herbicides C, Ca and Cb selected from the herbicides according to Table 34, c1-c150:
Mischung: 1.3.81 + O CbMixture: 1.3.81 + OCb
c1 16.c2.L3.81 c2.L3.81 (1.3.81 + Clodinafop-propargyl (c2)) Pendimethalin (c1 16) c132.c2.1.3.81 c2.L3.81 (1.3.81 + Clodinafop-propargyl (c2)) Pyroxasulfone (c132) c123.c2.L3.81 c2.L3.81 (1.3.81 + Clodinafop-propargyl (c2)) Flufenacet (c123)c1 16.c2.L3.81 c2.L3.81 (1.3.81 + clodinafop-propargyl (c2)) pendimethalin (c1 16) c132.c2.1.3.81 c2.L3.81 (1.3.81 + clodinafop-propargyl (c2)) pyroxasulfones (c132) c123.c2.L3.81 c2.L3.81 (1.3.81 + clodinafop-propargyl (c2)) flufenacet (c123)
C101 .C2.1.3.81 c2.L3.81 (1.3.81 + Clodinafop-propargyl (c2)) Picolinafen (c101 ) c94.c2.1.3.81 c2.L3.81 (1.3.81 + Clodinafop-propargyl (c2)) Diflufenican (c94) c96.c2.1.3.81 c2.L3.81 (1.3.81 + Clodinafop-propargyl (c2)) Beflubutamid (c96) c97.c2.1.3.81 c2.L3.81 (1.3.81 + Clodinafop-propargyl (c2)) Flurtamone (c97) c69.c2.1.3.81 c2.L3.81 (1.3.81 + Clodinafop-propargyl (c2)) Isoproturon (c69) c64.c2.1.3.81 c2.L3.81 (1.3.81 + Clodinafop-propargyl (c2)) Chlortoluron (c64) c63.c2.1.3.81 c2.L3.81 (1.3.81 + Clodinafop-propargyl (c2)) Bromoxynil (c63) c68.c2.1.3.81 c2.L3.81 (1.3.81 + Clodinafop-propargyl (c2)) loxynil (c68) c1 16.c5.L3.81 c5.L3.81 (1.3.81 + Fenoxaprop-P-ethyl (c5)) Pendimethalin (c1 16) c132.c5.L3.81 c5.L3.81 (1.3.81 + Fenoxaprop-P-ethyl (c5)) Pyroxasulfone (c132) c123.c5.L3.81 c5.L3.81 (1.3.81 + Fenoxaprop-P-ethyl (c5)) Flufenacet (c123) c101 .c5.L3.81 c5.L3.81 (1.3.81 + Fenoxaprop-P-ethyl (c5)) Picolinafen (c101 ) c94.c5.L3.81 c5.L3.81 (1.3.81 + Fenoxaprop-P-ethyl (c5)) Diflufenican (c94) c96.c5.L3.81 c5.L3.81 (1.3.81 + Fenoxaprop-P-ethyl (c5)) Beflubutamid (c96) c97.c5.L3.81 c5.L3.81 (1.3.81 + Fenoxaprop-P-ethyl (c5)) Flurtamone (c97) c69.c5.L3.81 c5.L3.81 (1.3.81 + Fenoxaprop-P-ethyl (c5)) Isoproturon (c69) c64.c5.L3.81 c5.L3.81 (1.3.81 + Fenoxaprop-P-ethyl (c5)) Chlortoluron (c64) c63.c5.L3.81 c5.L3.81 (1.3.81 + Fenoxaprop-P-ethyl (c5)) Bromoxynil (c63) c68.c5.L3.81 c5.L3.81 (1.3.81 + Fenoxaprop-P-ethyl (c5)) loxynil (c68) c1 16.c7.L3.81 c7.L3.81 (1.3.81 + Diclofop-methyl (c7)) Pendimethalin (c1 16) c132.c7.L3.81 c7.L3.81 (1.3.81 + Diclofop-methyl (c7)) Pyroxasulfone (c132) c123.c7.L3.81 c7.L3.81 (1.3.81 + Diclofop-methyl (c7)) Flufenacet (c123) c101 .c7.L3.81 c7.L3.81 (1.3.81 + Diclofop-methyl (c7)) Picolinafen (c101 ) c94.c7.L3.81 c7.L3.81 (1.3.81 + Diclofop-methyl (c7)) Diflufenican (c94) c96.c7.L3.81 c7.L3.81 (1.3.81 + Diclofop-methyl (c7)) Beflubutamid (c96) c97.c7.L3.81 c7.L3.81 (1.3.81 + Diclofop-methyl (c7)) Flurtamone (c97) c69.c7.L3.81 c7.L3.81 (1.3.81 + Diclofop-methyl (c7)) Isoproturon (c69) c64.c7.L3.81 c7.L3.81 (1.3.81 + Diclofop-methyl (c7)) Chlortoluron (c64) c63.c7.L3.81 c7.L3.81 (1.3.81 + Diclofop-methyl (c7)) Bromoxynil (c63) c68.c7.L3.81 c7.L3.81 (1.3.81 + Diclofop-methyl (c7)) loxynil (c68) c1 16.c12.L3.81 c12.L3.81 (1.3.81 + Tralkoxydim (c12)) Pendimethalin (c1 16) c132.c12.l.3.81 c12.L3.81 (1.3.81 + Tralkoxydim (d 2)) Pyroxasulfone (c132) c123.c12.L3.81 c12.L3.81 (1.3.81 + Tralkoxydim (d 2)) Flufenacet (c123) c101 .c12.L3.81 c12.L3.81 (1.3.81 + Tralkoxydim (d 2)) Picolinafen (c101 ) c94.c12.L3.81 c12.L3.81 (1.3.81 + Tralkoxydim (d 2)) Diflufenican (c94) c96.c12.L3.81 c12.L3.81 (1.3.81 + Tralkoxydim (d 2)) Beflubutamid (c96) c97.c12.L3.81 c12.L3.81 (1.3.81 + Tralkoxydim (d 2)) Flurtamone (c97) c69.c12.L3.81 c12.L3.81 (1.3.81 + Tralkoxydim (d 2)) Isoproturon (c69) c64.c12.L3.81 c12.L3.81 (1.3.81 + Tralkoxydim (c12)) Chlortoluron (c64) c63.c12.L3.81 c12.L3.81 (1.3.81 + Tralkoxydim (d 2)) Bromoxynil (c63) c68.c12.L3.81 c12.L3.81 (1.3.81 + Tralkoxydim (d 2)) loxynil (c68) c1 16.c8.L3.81 c8.L3.81 (1.3.81 + Pinoxaden (c8)) Pendimethalin (c1 16) c132.c8.L3.81 c8.L3.81 (1.3.81 + Pinoxaden (c8)) Pyroxasulfone (c132) c123.c8.L3.81 c8.L3.81 (1.3.81 + Pinoxaden (c8)) Flufenacet (c123) c101 .c8.L3.81 c8.L3.81 (1.3.81 + Pinoxaden (c8)) Picolinafen (c101 ) c94.c8.l.3.81 c8.L3.81 (1.3.81 + Pinoxaden (c8)) Diflufenican (c94) c96.c8.L3.81 c8.L3.81 (1.3.81 + Pinoxaden (c8)) Beflubutamid (c96) c97.c8.l.3.81 c8.L3.81 (1.3.81 + Pinoxaden (c8)) Flurtamone (c97) c69.c8.L3.81 c8.L3.81 (1.3.81 + Pinoxaden (c8)) Isoproturon (c69) c64.c8.l.3.81 c8.L3.81 (1.3.81 + Pinoxaden (c8)) Chlortoluron (c64) c63.c8.L3.81 c8.L3.81 (1.3.81 + Pinoxaden (c8)) Bromoxynil (c63) c68.c8.L3.81 c8.L3.81 (1.3.81 + Pinoxaden (c8)) loxynil (c68) c1 16.c40.L3.81 c40.L3.81 (1.3.81 + Mesosulfuron-m. (c40)) Pendimethalin (c1 16) c132.c40.L3.81 c40.L3.81 (1.3.81 + Mesosulfuron-m. (c40)) Pyroxasulfone (c132) c123.c40.L3.81 c40.L3.81 (1.3.81 + Mesosulfuron-m. (c40)) Flufenacet (c123) c101 .c40.L3.81 c40.L3.81 (1.3.81 + Mesosulfuron-m. (c40)) Picolinafen (c101 ) c94.c40.l.3.81 c40.L3.81 (1.3.81 + Mesosulfuron-m. (c40)) Diflufenican (c94) c96.c40.L3.81 c40.L3.81 (1.3.81 + Mesosulfuron-m. (c40)) Beflubutamid (c96) c97.c40.L3.81 c40.L3.81 (1.3.81 + Mesosulfuron-m. (c40)) Flurtamone (c97) c69.c40.L3.81 c40.L3.81 (1.3.81 + Mesosulfuron-m. (c40)) Isoproturon (c69) c64.c40.L3.81 c40.L3.81 (1.3.81 + Mesosulfuron-m. (c40)) Chlortoluron (c64) c63.c40.L3.81 c40.L3.81 (1.3.81 + Mesosulfuron-m. (c40)) Bromoxynil (c63) c68.c40.L3.81 c40.L3.81 (1.3.81 + Mesosulfuron-m. (c40)) loxynil (c68) c1 16.c30.L3.81 c30.L3.81 (1.3.81 + Flupyrsulfuron-m.-s. (c30)) Pendimethalin (c1 16) c132.c30.L3.81 c30.L3.81 (1.3.81 + Flupyrsulfuron-m.-s. (c30)) Pyroxasulfone (c132) c123.c30.L3.81 c30.L3.81 (1.3.81 + Flupyrsulfuron-m.-s. (c30)) Flufenacet (c123) c101 .c30.L3.81 c30.L3.81 (1.3.81 + Flupyrsulfuron-m.-s. (c30)) Picolinafen (c101 ) c94.c30.l.3.81 c30.L3.81 (1.3.81 + Flupyrsulfuron-m.-s. (c30)) Diflufenican (c94) c96.c30.L3.81 c30.L3.81 (1.3.81 + Flupyrsulfuron-m.-s. (c30)) Beflubutamid (c96) c97.c30.l.3.81 c30.L3.81 (1.3.81 + Flupyrsulfuron-m.-s. (c30)) Flurtamone (c97) c69.c30.L3.81 c30.L3.81 (1.3.81 + Flupyrsulfuron-m.-s. (c30)) Isoproturon (c69) c64.c30.l.3.81 c30.L3.81 (1.3.81 + Flupyrsulfuron-m.-s. (c30)) Chlortoluron (c64) c63.c30.L3.81 c30.L3.81 (1.3.81 + Flupyrsulfuron-m.-s. (c30)) Bromoxynil (c63) c68.c30.L3.81 c30.L3.81 (1.3.81 + Flupyrsulfuron-m.-s. (c30)) loxynil (c68) c1 16.c54.L3.81 c54.L3.81 (1.3.81 + Sulfosulfuron (c54)) Pendimethalin (c1 16) c132.c54.L3.81 c54.L3.81 (1.3.81 + Sulfosulfuron (c54)) Pyroxasulfone (c132) c123.c54.L3.81 c54.L3.81 (1.3.81 + Sulfosulfuron (c54)) Flufenacet (c123) c101 .c54.L3.81 c54.L3.81 (1.3.81 + Sulfosulfuron (c54)) Picolinafen (c101 ) c94.c54.L3.81 c54.L3.81 (1.3.81 + Sulfosulfuron (c54)) Diflufenican (c94) c96.c54.L3.81 c54.L3.81 (1.3.81 + Sulfosulfuron (c54)) Beflubutamid (c96) c97.c54.l.3.81 c54.L3.81 (1.3.81 + Sulfosulfuron (c54)) Flurtamone (c97) c69.c54.L3.81 c54.L3.81 (1.3.81 + Sulfosulfuron (c54)) Isoproturon (c69) c64.c54.L3.81 c54.L3.81 (1.3.81 + Sulfosulfuron (c54)) Chlortoluron (c64) c63.c54.L3.81 c54.L3.81 (1.3.81 + Sulfosulfuron (c54)) Bromoxynil (c63) c68.c54.L3.81 c54.L3.81 (1.3.81 + Sulfosulfuron (c54)) loxynil (c68) c1 16.c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron-m.-s. (c39)) Pendimethalin (c1 16) c132.c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron-m.-s. (c39)) Pyroxasulfone (c132) c123.c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron-m.-s. (c39)) Flufenacet (c123) c101 .c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron-m.-s. (c39)) Picolinafen (c101 ) c94.c39.l.3.81 c39.L3.81 (1.3.81 + lodosulfuron-m.-s. (c39)) Diflufenican (c94) c96.c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron-m.-s. (c39)) Beflubutamid (c96) c97.c39.l.3.81 c39.L3.81 (1.3.81 + lodosulfuron-m.-s. (c39)) Flurtamone (c97) c69.c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron-m.-s. (c39)) Isoproturon (c69) c64.c39.l.3.81 c39.L3.81 (1.3.81 + lodosulfuron-m.-s. (c39)) Chlortoluron (c64) c63.c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron-m.-s. (c39)) Bromoxynil (c63) c68.c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron-m.-s. (c39)) loxynil (c68) c1 16.c54.L3.81 c54.L3.81 (1.3.81 + Amidosulfuron (c54)) Pendimethalin (c1 16) c132.c54.L3.81 c54.L3.81 (1.3.81 + Amidosulfuron (c54)) Pyroxasulfone (c132) c123.c54.L3.81 c54.L3.81 (1.3.81 + Amidosulfuron (c54)) Flufenacet (c123) c101 .c54.L3.81 c54.L3.81 (1.3.81 + Amidosulfuron (c54)) Picolinafen (c101 ) c94.c54.L3.81 c54.L3.81 (1.3.81 + Amidosulfuron (c54)) Diflufenican (c94) c96.c54.L3.81 c54.L3.81 (1.3.81 + Amidosulfuron (c54)) Beflubutamid (c96) c97.c54.l.3.81 c54.L3.81 (1.3.81 + Amidosulfuron (c54)) Flurtamone (c97) c69.c54.L3.81 c54.L3.81 (1.3.81 + Amidosulfuron (c54)) Isoproturon (c69) c64.c54.L3.81 c54.L3.81 (1.3.81 + Amidosulfuron (c54)) Chlortoluron (c64) c63.c54.L3.81 c54.L3.81 (1.3.81 + Amidosulfuron (c54)) Bromoxynil (c63) c68.c54.L3.81 c54.L3.81 (1.3.81 + Amidosulfuron (c54)) loxynil (c68) c1 16.c42.L3.81 c42.L3.81 (1.3.81 + Metsulfuron-m. (c42)) Pendimethalin (c1 16) c132.c42.L3.81 c42.L3.81 (1.3.81 + Metsulfuron-m. (c42)) Pyroxasulfone (c132) c123.c42.L3.81 c42.L3.81 (1.3.81 + Metsulfuron-m. (c42)) Flufenacet (c123) c101 .c42.L3.81 c42.L3.81 (1.3.81 + Metsulfuron-m. (c42)) Picolinafen (c101 ) c94.c42.l.3.81 c42.L3.81 (1.3.81 + Metsulfuron-m. (c42)) Diflufenican (c94) c96.c42.L3.81 c42.L3.81 (1.3.81 + Metsulfuron-m. (c42)) Beflubutamid (c96) c97.c42.L3.81 c42.L3.81 (1.3.81 + Metsulfuron-m. (c42)) Flurtamone (c97) c69.c42.L3.81 c42.L3.81 (1.3.81 + Metsulfuron-m. (c42)) Isoproturon (c69) c64.c42.L3.81 c42.L3.81 (1.3.81 + Metsulfuron-m. (c42)) Chlortoluron (c64) c63.c42.L3.81 c42.L3.81 (1.3.81 + Metsulfuron-m. (c42)) Bromoxynil (c63) c68.c42.L3.81 c42.L3.81 (1.3.81 + Metsulfuron-m. (c42)) loxynil (c68) c1 16.c56.L3.81 c56.L3.81 (1.3.81 + Thifensulfuron-m. (c56)) Pendimethalin (c1 16) c132.c56.L3.81 c56.L3.81 (1.3.81 + Thifensulfuron-m. (c56)) Pyroxasulfone (c132) c123.c56.L3.81 c56.L3.81 (1.3.81 + Thifensulfuron-m. (c56)) Flufenacet (c123) c101 .c56.L3.81 c56.L3.81 (1.3.81 + Thifensulfuron-m. (c56)) Picolinafen (c101 ) c94.c56.L3.81 c56.L3.81 (1.3.81 + Thifensulfuron-m. (c56)) Diflufenican (c94) c96.c56.L3.81 c56.L3.81 (1.3.81 + Thifensulfuron-m. (c56)) Beflubutamid (c96) c97.c56.L3.81 c56.L3.81 (1.3.81 + Thifensulfuron-m. (c56)) Flurtamone (c97) c69.c56.L3.81 c56.L3.81 (1.3.81 + Thifensulfuron-m. (c56)) Isoproturon (c69) c64.c56.L3.81 c56.L3.81 (1.3.81 + Thifensulfuron-m. (c56)) Chlortoluron (c64) c63.c56.L3.81 c56.L3.81 (1.3.81 + Thifensulfuron-m. (c56)) Bromoxynil (c63) c68.c56.L3.81 c56.L3.81 (1.3.81 + Thifensulfuron-m. (c56)) loxynil (c68) c1 16.c57.L3.81 c57.L3.81 (1.3.81 + Tribenuron-m. (c57)) Pendimethalin (c1 16) c132.c57.L3.81 c57.L3.81 (1.3.81 + Tribenuron-m. (c57)) Pyroxasulfone (c132) c123.c57.L3.81 c57.L3.81 (1.3.81 + Tribenuron-m. (c57)) Flufenacet (c123) c101 .c57.L3.81 c57.L3.81 (1.3.81 + Tribenuron-m. (c57)) Picolinafen (c101 ) c94.c57.L3.81 c57.L3.81 (1.3.81 + Tribenuron-m. (c57)) Diflufenican (c94) c96.c57.L3.81 c57.L3.81 (1.3.81 + Tribenuron-m. (c57)) Beflubutamid (c96) c97.c57.L3.81 c57.L3.81 (1.3.81 + Tribenuron-m. (c57)) Flurtamone (c97) c69.c57.L3.81 c57.L3.81 (1.3.81 + Tribenuron-m. (c57)) Isoproturon (c69) c64.c57.L3.81 c57.L3.81 (1.3.81 + Tribenuron-m. (c57)) Chlortoluron (c64) c63.c57.L3.81 c57.L3.81 (1.3.81 + Tribenuron-m. (c57)) Bromoxynil (c63) c68.c57.L3.81 c57.L3.81 (1.3.81 + Tribenuron-m. (c57)) loxynil (c68) c1 16.c59.L3.81 c59.L3.81 (1.3.81 + Tritosulfuron (c59)) Pendimethalin (c1 16) c132.c59.L3.81 c59.L3.81 (1.3.81 + Tritosulfuron (c59)) Pyroxasulfone (c132) c123.c59.L3.81 c59.L3.81 (1.3.81 + Tritosulfuron (c59)) Flufenacet (c123) c101 .c59.L3.81 c59.L3.81 (1.3.81 + Tritosulfuron (c59)) Picolinafen (c101 ) c94.c59.L3.81 c59.L3.81 (1.3.81 + Tritosulfuron (c59)) Diflufenican (c94) c96.c59.L3.81 c59.L3.81 (1.3.81 + Tritosulfuron (c59)) Beflubutamid (c96) c97.c59.l.3.81 c59.L3.81 (1.3.81 + Tritosulfuron (c59)) Flurtamone (c97) c69.c59.L3.81 c59.L3.81 (1.3.81 + Tritosulfuron (c59)) Isoproturon (c69) c64.c59.L3.81 c59.L3.81 (1.3.81 + Tritosulfuron (c59)) Chlortoluron (c64) c63.c59.L3.81 c59.L3.81 (1.3.81 + Tritosulfuron (c59)) Bromoxynil (c63) c68.c59.L3.81 c59.L3.81 (1.3.81 + Tritosulfuron (c59)) loxynil (c68) c1 16.c25.L3.81 c25.L3.81 (1.3.81 + Orthosulfamuron (c25)) Pendimethalin (c1 16) c132.c25.L3.81 c25.L3.81 (1.3.81 + Orthosulfamuron (c25)) Pyroxasulfone (c132) c123.c25.L3.81 c25.L3.81 (1.3.81 + Orthosulfamuron (c25)) Flufenacet (c123) c101 .c25.L3.81 c25.L3.81 (1.3.81 + Orthosulfamuron (c25)) Picolinafen (c101 ) c94.c25.l.3.81 c25.L3.81 (1.3.81 + Orthosulfamuron (c25)) Diflufenican (c94) c96.c25.L3.81 c25.L3.81 (1.3.81 + Orthosulfamuron (c25)) Beflubutamid (c96) c97.c25.l.3.81 c25.L3.81 (1.3.81 + Orthosulfamuron (c25)) Flurtamone (c97) c69.c25.L3.81 c25.L3.81 (1.3.81 + Orthosulfamuron (c25)) Isoproturon (c69) c64.c25.l.3.81 c25.L3.81 (1.3.81 + Orthosulfamuron (c25)) Chlortoluron (c64) c63.c25.L3.81 c25.L3.81 (1.3.81 + Orthosulfamuron (c25)) Bromoxynil (c63) c68.c25.L3.81 c25.L3.81 (1.3.81 + Orthosulfamuron (c25)) loxynil (c68) c1 16.c50.L3.81 c50.L3.81 (1.3.81 + Pyroxsulam (c50)) Pendimethalin (c1 16) c132.c50.L3.81 c50.L3.81 (1.3.81 + Pyroxsulam (c50)) Pyroxasulfone (c132) c123.c50.L3.81 c50.L3.81 (1.3.81 + Pyroxsulam (c50)) Flufenacet (c123) c101 .c50.L3.81 c50.L3.81 (1.3.81 + Pyroxsulam (c50)) Picolinafen (c101 ) c94.c50.L3.81 c50.L3.81 (1.3.81 + Pyroxsulam (c50)) Diflufenican (c94) c96.c50.L3.81 c50.L3.81 (1.3.81 + Pyroxsulam (c50)) Beflubutamid (c96) c97.c50.l.3.81 c50.L3.81 (1.3.81 + Pyroxsulam (c50)) Flurtamone (c97) c69.c50.L3.81 c50.L3.81 (1.3.81 + Pyroxsulam (c50)) Isoproturon (c69) c64.c50.L3.81 c50.L3.81 (1.3.81 + Pyroxsulam (c50)) Chlortoluron (c64) c63.c50.L3.81 c50.L3.81 (1.3.81 + Pyroxsulam (c50)) Bromoxynil (c63) c68.c50.L3.81 c50.L3.81 (1.3.81 + Pyroxsulam (c50)) loxynil (c68) c1 16.c45.L3.81 c45.L3.81 (1.3.81 + Penoxsulam (c45)) Pendimethalin (c1 16) c132.c45.L3.81 c45.L3.81 (1.3.81 + Penoxsulam (c45)) Pyroxasulfone (c132) c123.c45.L3.81 c45.L3.81 (1.3.81 + Penoxsulam (c45)) Flufenacet (c123) c101 .c45.L3.81 c45.L3.81 (1.3.81 + Penoxsulam (c45)) Picolinafen (c101 ) c94.c45.L3.81 c45.L3.81 (1.3.81 + Penoxsulam (c45)) Diflufenican (c94) c96.c45.L3.81 c45.L3.81 (1.3.81 + Penoxsulam (c45)) Beflubutamid (c96) c97.c45.L3.81 c45.L3.81 (1.3.81 + Penoxsulam (c45)) Flurtamone (c97) c69.c45.L3.81 c45.L3.81 (1.3.81 + Penoxsulam (c45)) Isoproturon (c69) c64.c45.L3.81 c45.L3.81 (1.3.81 + Penoxsulam (c45)) Chlortoluron (c64) c63.c45.L3.81 c45.L3.81 (1.3.81 + Penoxsulam (c45)) Bromoxynil (c63) c68.c45.L3.81 c45.L3.81 (1.3.81 + Penoxsulam (c45)) loxynil (c68) c1 16.c27.L3.81 c27.L3.81 (1.3.81 + Florasulam (c27)) Pendimethalin (c1 16) c132.c27.L3.81 c27.L3.81 (1.3.81 + Florasulam (c27)) Pyroxasulfone (c132) c123.c27.L3.81 c27.L3.81 (1.3.81 + Florasulam (c27)) Flufenacet (c123) c101 .c27.L3.81 c27.L3.81 (1.3.81 + Florasulam (c27)) Picolinafen (c101 ) c94.c27.l.3.81 c27.L3.81 (1.3.81 + Florasulam (c27)) Diflufenican (c94) c96.c27.L3.81 c27.L3.81 (1.3.81 + Florasulam (c27)) Beflubutamid (c96) c97.c27.l.3.81 c27.L3.81 (1.3.81 + Florasulam (c27)) Flurtamone (c97) c69.c27.L3.81 c27.L3.81 (1.3.81 + Florasulam (c27)) Isoproturon (c69) c64.c27.l.3.81 c27.L3.81 (1.3.81 + Florasulam (c27)) Chlortoluron (c64) c63.c27.L3.81 c27.L3.81 (1.3.81 + Florasulam (c27)) Bromoxynil (c63) c68.c27.L3.81 c27.L3.81 (1.3.81 + Florasulam (c27)) loxynil (c68) c1 16.c46.L3.81 c46.L3.81 (1.3.81 + Propoxy-carbazon (c46)) Pendimethalin (c1 16) c132.c46.L3.81 c46.L3.81 (1.3.81 + Propoxy-carbazon (c46)) Pyroxasulfone (c132) c123.c46.L3.81 c46.L3.81 (1.3.81 + Propoxy-carbazon (c46)) Flufenacet (c123) c101 .c46.L3.81 c46.L3.81 (1.3.81 + Propoxy-carbazon (c46)) Picolinafen (c101 ) c94.c46.L3.81 c46.L3.81 (1.3.81 + Propoxy-carbazon (c46)) Diflufenican (c94) c96.c46.L3.81 c46.L3.81 (1.3.81 + Propoxy-carbazon (c46)) Beflubutamid (c96) c97.c46.L3.81 c46.L3.81 (1.3.81 + Propoxy-carbazon (c46)) Flurtamone (c97) c69.c46.L3.81 c46.L3.81 (1.3.81 + Propoxy-carbazon (c46)) Isoproturon (c69) c64.c46.L3.81 c46.L3.81 (1.3.81 + Propoxy-carbazon (c46)) Chlortoluron (c64) c63.c46.L3.81 c46.L3.81 (1.3.81 + Propoxy-carbazon (c46)) Bromoxynil (c63) c68.c46.L3.81 c46.L3.81 (1.3.81 + Propoxy-carbazon (c46)) loxynil (c68) c1 16.c28.L3.81 c28.L3.81 (1.3.81 + Flucarbazone-s. (c28)) Pendimethalin (c1 16) c132.c28.L3.81 c28.L3.81 (1.3.81 + Flucarbazone-s. (c28)) Pyroxasulfone (c132) c123.c28.L3.81 c28.L3.81 (1.3.81 + Flucarbazone-s. (c28)) Flufenacet (c123) c101 .c28.L3.81 c28.L3.81 (1.3.81 + Flucarbazone-s. (c28)) Picolinafen (c101 ) c94.c28.l.3.81 c28.L3.81 (1.3.81 + Flucarbazone-s. (c28)) Diflufenican (c94) c96.c28.L3.81 c28.L3.81 (1.3.81 + Flucarbazone-s. (c28)) Beflubutamid (c96) c97.c28.l.3.81 c28.L3.81 (1.3.81 + Flucarbazone-s. (c28)) Flurtamone (c97) c69.c28.L3.81 c28.L3.81 (1.3.81 + Flucarbazone-s. (c28)) Isoproturon (c69) c64.c28.l.3.81 c28.L3.81 (1.3.81 + Flucarbazone-s. (c28)) Chlortoluron (c64) c63.c28.L3.81 c28.L3.81 (1.3.81 + Flucarbazone-s. (c28)) Bromoxynil (c63) c68.c28.L3.81 c28.L3.81 (1.3.81 + Flucarbazone-s. (c28)) loxynil (c68) c1 16.c55.L3.81 c55.1.3.81 (1.3.81 + Thiencarbazon-m. (c55)) Pendimethalin (c1 16) c132.c55.L3.81 c55.1.3.81 (1.3.81 + Thiencarbazon-m. (c55)) Pyroxasulfone (c132) c123.c55.L3.81 c55.1.3.81 (1.3.81 + Thiencarbazon-m. (c55)) Flufenacet (c123) c101 .c55.L3.81 c55.1.3.81 (1.3.81 + Thiencarbazon-m. (c55)) Picolinafen (c101 ) c94.c55.L3.81 c55.1.3.81 (1.3.81 + Thiencarbazon-m. (c55)) Diflufenican (c94) c96.c55.L3.81 c55.1.3.81 (1.3.81 + Thiencarbazon-m. (c55)) Beflubutamid (c96) c97.c55.L3.81 c55.1.3.81 (1.3.81 + Thiencarbazon-m. (c55)) Flurtamone (c97) c69.c55.L3.81 c55.1.3.81 (1.3.81 + Thiencarbazon-m. (c55)) Isoproturon (c69) c64.c55.L3.81 c55.1.3.81 (1.3.81 + Thiencarbazon-m. (c55)) Chlortoluron (c64) c63.c55.L3.81 c55.1.3.81 (1.3.81 + Thiencarbazon-m. (c55)) Bromoxynil (c63) c68.c55.L3.81 c55.1.3.81 (1.3.81 + Thiencarbazon-m. (c55)) loxynil (c68) c1 16.c33.L3.81 c33.L3.81 (1.3.81 + Imazamox (c33)) Pendimethalin (c1 16) c132.c33.l.3.81 c33.L3.81 (1.3.81 + Imazamox (c33)) Pyroxasulfone (c132) c123.c33.L3.81 c33.L3.81 (1.3.81 + Imazamox (c33)) Flufenacet (c123) c101 .c33.L3.81 c33.L3.81 (1.3.81 + Imazamox (c33)) Picolinafen (c101 ) c94.c33.l.3.81 c33.L3.81 (1.3.81 + Imazamox (c33)) Diflufenican (c94) c96.c33.L3.81 c33.L3.81 (1.3.81 + Imazamox (c33)) Beflubutamid (c96) c97.c33.l.3.81 c33.L3.81 (1.3.81 + Imazamox (c33)) Flurtamone (c97) c69.c33.L3.81 c33.L3.81 (1.3.81 + Imazamox (c33)) Isoproturon (c69) c64.c33.l.3.81 c33.L3.81 (1.3.81 + Imazamox (c33)) Chlortoluron (c64) c63.c33.L3.81 c33.L3.81 (1.3.81 + Imazamox (c33)) Bromoxynil (c63) c68.c33.L3.81 c33.L3.81 (1.3.81 + Imazamox (c33)) loxynil (c68) c1 16.c32.L3.81 c32.L3.81 (1.3.81 + Imazamethabenz-m. Pendimethalin (c1 16)C101 .C2.1.3.81 c2.L3.81 (1.3.81 + clodinafop-propargyl (c2)) picolinafen (c101) c94.c2.1.3.81 c2.L3.81 (1.3.81 + clodinafop-propargyl (c2 )) Diflufenican (c94) c96.c2.1.3.81 c2.L3.81 (1.3.81 + Clodinafop-propargyl (c2)) Beflubutamide (c96) c97.c2.1.3.81 c2.L3.81 (1.3.81 + Clodinafop-propargyl (c2)) flurtamone (c97) c69.c2.1.3.81 c2.L3.81 (1.3.81 + clodinafop-propargyl (c2)) isoproturon (c69) c64.c2.1.3.81 c2.L3 .81 (1.3.81 + clodinafop-propargyl (c2)) chlortoluron (c64) c63.c2.1.3.81 c2.L3.81 (1.3.81 + clodinafop-propargyl (c2)) bromoxynil (c63) c68.c2. 1.3.81 c2.L3.81 (1.3.81 + clodinafop-propargyl (c2)) loxynil (c68) c1 16.c5.L3.81 c5.L3.81 (1.3.81 + fenoxaprop-P-ethyl (c5) ) Pendimethalin (c1 16) c132.c5.L3.81 c5.L3.81 (1.3.81 + fenoxaprop-P-ethyl (c5)) pyroxasulfones (c132) c123.c5.L3.81 c5.L3.81 (1.3 .81 + fenoxaprop-P-ethyl (c5)) flufenacet (c123) c101 .c5.L3.81 c5.L3.81 (1.3.81 + fenoxaprop-P-ethyl (c5)) picolinafen (c101) c94.c5. L3.81 c5.L3.81 (1.3.81 + fenoxaprop-P-ethyl (c5)) Dif lufenican (c94) c96.c5.L3.81 c5.L3.81 (1.3.81 + fenoxaprop-P-ethyl (c5)) beflubutamide (c96) c97.c5.L3.81 c5.L3.81 (1.3.81 + Fenoxaprop-P-ethyl (c5)) flurtamone (c97) c69.c5.L3.81 c5.L3.81 (1.3.81 + fenoxaprop-P-ethyl (c5)) isoproturon (c69) c64.c5.L3.81 c5.L3.81 (1.3.81 + fenoxaprop-P-ethyl (c5)) chlorotoluron (c64) c63.c5.L3.81 c5.L3.81 (1.3.81 + fenoxaprop-P -ethyl (c5)) bromoxynil (c63) c68.c5.L3.81 c5.L3.81 (1.3.81 + fenoxaprop-P-ethyl (c5)) loxynil (c68) c1 16.c7.L3.81 c7. L3.81 (1.3.81 + diclofop-methyl (c7)) pendimethalin (c1 16) c132.c7.L3.81 c7.L3.81 (1.3.81 + diclofop-methyl (c7)) pyroxasulfones (c132) c123. c7.L3.81 c7.L3.81 (1.3.81 + diclofop-methyl (c7)) flufenacet (c123) c101 .c7.L3.81 c7.L3.81 (1.3.81 + diclofop-methyl (c7)) Picolinafen (c101) c94.c7.L3.81 c7.L3.81 (1.3.81 + diclofopmethyl (c7)) diflufenican (c94) c96.c7.L3.81 c7.L3.81 (1.3.81 + diclofop -methyl (c7)) Beflubutamide (c96) c97.c7.L3.81 c7.L3.81 (1.3.81 + Diclofop-methyl (c7)) Flurtamone (c97) c69.c7.L3.81 c7.L3.81 (1.3.81 + diclofop-methyl (c7)) isoproturon (c69) c64.c7.L3.81 c7.L3.81 (1.3.81 + diclofop-methyl (c7)) chlorotoluron (c64) c63.c7.L3. 81 c7.L3.81 (1.3.81 + diclofop-methyl (c7)) bromoxynil (c63) c68.c7.L3.81 c7.L3.81 (1.3.81 + diclofop-me thyl (c7)) loxynil (c68) c1 16.c12.L3.81 c12.L3.81 (1.3.81 + tralkoxydim (c12)) pendimethalin (c1 16) c132.c12.l.3.81 c12.L3.81 ( 1.3.81 + tralkoxydim (d2)) pyroxasulfones (c132) c123.c12.L3.81 c12.L3.81 (1.3.81 + tralkoxydim (d2)) flufenacet (c123) c101 .c12.L3.81 c12. L3.81 (1.3.81 + tralkoxydim (d2)) picolinafen (c101) c94.c12.L3.81 c12.L3.81 (1.3.81 + tralkoxydim (d2)) diflufenican (c94) c96.c12.L3 .81 c12.L3.81 (1.3.81 + tralkoxydim (d2)) beflubutamide (c96) c97.c12.L3.81 c12.L3.81 (1.3.81 + tralkoxydim (d2)) flurtamone (c97) c69 .c12.L3.81 c12.L3.81 (1.3.81 + tralkoxydim (d2)) isoproturon (c69) c64.c12.L3.81 c12.L3.81 (1.3.81 + tralkoxydim (c12)) chlorotoluron ( c64) c63.c12.L3.81 c12.L3.81 (1.3.81 + tralkoxydim (d 2)) bromoxynil (c63) c68.c12.L3.81 c12.L3.81 (1.3.81 + tralkoxydim (d 2 )) loxynil (c68) c1 16.c8.L3.81 c8.L3.81 (1.3.81 + pinoxaden (c8)) pendimethalin (c1 16) c132.c8.L3.81 c8.L3.81 (1.3.81 + Pinoxaden (c8)) Pyroxasulfone (c132) c123.c8.L3.81 c8.L3.81 (1.3.81 + Pinoxa the (c8)) flufenacet (c123) c101 .c8.L3.81 c8.L3.81 (1.3.81 + pinoxaden (c8)) picolinafen (c101) c94.c8.l.3.81 c8.L3.81 (1.3. 81 + pinoxaden (c8)) diflufenican (c94) c96.c8.L3.81 c8.L3.81 (1.3.81 + pinoxaden (c8)) beflubutamide (c96) c97.c8.l.3.81 c8.L3.81 ( 1.3.81 + Pinoxaden (c8)) Flurtamone (c97) c69.c8.L3.81 c8.L3.81 (1.3.81 + Pinoxaden (c8)) Isoproturon (c69) c64.c8.l.3.81 c8.L3. 81 (1.3.81 + Pinoxaden (c8)) Chlortoluron (c64) c63.c8.L3.81 c8.L3.81 (1.3.81 + Pinoxaden (c8)) Bromoxynil (c63) c68.c8.L3.81 c8. L3.81 (1.3.81 + pinoxaden (c8)) loxynil (c68) c1 16.c40.L3.81 c40.L3.81 (1.3.81 + mesosulfuron-m. (c40)) pendimethalin (c1 16) c132.c40.L3.81 c40.L3.81 (1.3.81 + mesosulfuron-m. (c40)) pyroxasulfones (c132) c123.c40.L3.81 c40.L3.81 (1.3.81 + mesosulfuron-m. (C40)) flufenacet (c123) c101 .c40.L3.81 c40.L3.81 (1.3.81 + mesosulfuron-m. (C40)) picolinafen (c101) c94.c40.l.3.81 c40.L3.81 (1.3.81 + mesosulfuron-m. (c40)) diflufenican (c94) c96.c40.L3.81 c40.L3.81 (1.3.81 + mesosulfuron-m. (c40)) Beflubutamide (c96) c97.c40.L3.81 c40.L3.81 (1.3.81 + mesosulfuron-m. (c40)) Flurtamone (c97) c69.c40.L3.81 c40.L3.81 ( 1.3.81 + mesosulfuron-m. (C40)) isoproturon (c69) c64.c40.L3.81 c40.L3.81 (1.3.81 + mesosulfuron-m. (C40)) chlorotoluron (c64) c63.c40.L3 .81 c40.L3.81 (1.3.81 + mesosulfuron-m. (C40)) bromoxynil (c63) c68.c40.L3.81 c40.L3.81 (1.3.81 + mesosulfuron-m. (C40)) loxynil (c68) c1 16.c30.L3.81 c30.L3.81 (1.3.81 + flupyrsulfuron-m.-s. (c30)) pendimethalin (c1 16) c132.c30.L3.81 c30.L3.81 ( 1.3.81 + flupyrsulfuron-m.-s (c30)) pyroxasulfones (c132) c123.c30.L3.81 c30.L3.81 (1.3.81 + flupyrsulfuron-m.-s. (C30)) flufenacetate (c123 ) c101 .c30.L3.81 c30.L3.81 (1.3.81 + flupyrsulfuron-m.-s. (c30)) picolinafen (c101) c94.c30.l.3.81 c30.L3.81 (1.3.81 + Flupyrsulfuron-m.-s (c30)) diflufenican (c94) c96.c30.L3.81 c30.L3.81 (1.3.81 + flupyrsulfuron-m.-s. (C30) ) Beflubutamide (c96) c97.c30.l.3.81 c30.L3.81 (1.3.81 + flupyrsulfuron-m.-s. (c30)) Flurtamone (c97) c69.c30.L3.81 c30.L3.81 (1.3.81 + flupyrsulfuron-m.-s. (c30)) isoproturon (c69) c64.c30.l.3.81 c30.L3 .81 (1.3.81 + flupyrsulfuron-m.-s. (C30)) chlorotoluron (c64) c63.c30.L3.81 c30.L3.81 (1.3.81 + flupyrsulfuron-m.-s. (C30)) Bromoxynil (c63) c68.c30.L3.81 c30.L3.81 (1.3.81 + flupyrsulfuron-m.-s. (C30)) loxynil (c68) c1 16.c54.L3.81 c54.L3.81 ( 1.3.81 + sulfosulfuron (c54)) pendimethalin (c1 16) c132.c54.L3.81 c54.L3.81 (1.3.81 + sulfosulfuron (c54)) pyroxasulfones (c132) c123.c54.L3.81 c54.L3 .81 (1.3.81 + sulfosulfuron (c54)) flufenacet (c123) c101 .c54.L3.81 c54.L3.81 (1.3.81 + sulfosulfuron (c54)) picolinafen (c101) c94.c54.L3.81 c54 .L3.81 (1.3.81 + sulfosulfuron (c54)) diflufenican (c94) c96.c54.L3.81 c54.L3.81 (1.3.81 + sulfosulfuron (c54)) beflubutamide (c96) c97.c54.l. 3.81 c54.L3.81 (1.3.81 + sulfosulfuron (c54)) flurtamone (c97) c69.c54.L3.81 c54.L3.81 (1.3.81 + sulfosulfuron (c54)) isoproturon (c69) c64.c54. L3.81 c54.L3.81 (1.3.81 + sulfosulfuron (c54)) Chl ortoluron (c64) c63.c54.L3.81 c54.L3.81 (1.3.81 + sulfosulfuron (c54)) bromoxynil (c63) c68.c54.L3.81 c54.L3.81 (1.3.81 + sulfosulfuron (c54 )) loxynil (c68) c1 16.c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron-m.-s. (c39)) pendimethalin (c1 16) c132.c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron-m.-s. (c39)) pyroxasulfones (c132) c123.c39.L3.81 c39. L3.81 (1.3.81 + lodosulfuron-m.-s. (C39)) flufenacet (c123) c101 .c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron-m.-s. (C39) ) Picolinafen (c101) c94.c39.l.3.81 c39.L3.81 (1.3.81 + lodosulfuron-m.-s. (C39)) Diflufenican (c94) c96.c39.L3.81 c39.L3.81 ( 1.3.81 + lodosulfuron-m.-s. (C39)) Beflubutamide (c96) c97.c39.l.3.81 c39.L3.81 (1.3.81 + lodosulfuron-m.-s. (C39)) Flurtamone (c97 ) c69.c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron-m.-s. (c39)) isoproturon (c69) c64.c39.l.3.81 c39.L3.81 (1.3.81 + iodosulfuron-m.-s. (c39)) Chlorotoluron (c64) c63.c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron-m.-s. (c39)) Bromoxynil (c63) c68.c39 .L3.81 c39.L3.81 (1.3.81 + lodosulfuron-m.-s. (C39)) loxynil (c68) c1 16.c54.L3.81 c54.L3.81 (1.3.81 + amidosulfuron (c54)) pendimethalin (c1 16) c132.c54.L3.81 c54.L3.81 (1.3.81 + amidosulfuron (c54)) Pyroxasulfones (c132) c123.c54.L3.81 c54.L3.81 (1.3.81 + Amidosulfuron (c54)) Flufenacet (c123) c101 .c54.L3.81 c54.L3.81 (1.3.81 + Amidosulfuron (c54 )) Picolinafen (c101) c94.c54.L3.81 c54.L3.81 (1.3.81 + Amidosulfuron (c54)) Diflufenican (c94) c96.c54.L3.81 c54.L3.81 (1.3.81 + Amidosulfuron (c54)) Beflubutamide (c96) c97.c54.l.3.81 c54.L3.81 (1.3.81 + Amidosulfuron (c54)) Flurtamone (c97) c69.c54.L3.81 c54.L3.81 (1.3.81 + Amidosulfuron (c54)) isoproturon (c69) c64.c54.L3.81 c54.L3.81 (1.3.81 + amidosulfuron (c54)) chlorotoluron (c64) c63.c54.L3.81 c54.L3.81 (1.3 .81 + amidosulfuron (c54)) bromoxynil (c63) c68.c54.L3.81 c54.L3.81 (1.3.81 + amidosulfuron (c54)) loxynil (c68) c1 16.c42.L3.81 c42.L3. 81 (1.3.81 + metsulfuron-m. (C42)) pendimethalin (c1 16) c132.c42.L3.81 c42.L3.81 (1.3.81 + metsulfuron-m. (C42)) pyroxasulfones (c132) c123. c42.L3.81 c42.L3.81 ( 1.3.81 + metsulfuron-m. (c42)) flufenacet (c123) c101 .c42.L3.81 c42.L3.81 (1.3.81 + metsulfuron-m. (c42)) picolinafen (c101) c94.c42.l.3.81 c42.L3.81 ( 1.3.81 + metsulfuron-m. (C42)) diflufenican (c94) c96.c42.L3.81 c42.L3.81 (1.3.81 + metsulfuron-m. (C42)) beflubutamide (c96) c97.c42.L3 .81 c42.L3.81 (1.3.81 + metsulfuron-m. (C42)) flurtamone (c97) c69.c42.L3.81 c42.L3.81 (1.3.81 + metsulfuron-m. (C42)) isoproturon (c69) c64.c42.L3.81 c42.L3.81 (1.3.81 + metsulfuron-m. (c42)) chlorotoluron (c64) c63.c42.L3.81 c42.L3.81 (1.3.81 + metsulfuron -m. (c42)) Bromoxynil (c63) c68.c42.L3.81 c42.L3.81 (1.3.81 + metsulfuron-m. (c42)) loxynil (c68) c1 16.c56.L3.81 c56. L3.81 (1.3.81 + thifensulfuron-m. (C56)) pendimethalin (c1 16) c132.c56.L3.81 c56.L3.81 (1.3.81 + thifensulfuron-m. (C56)) pyroxasulfones (c132) c123.c56.L3.81 c56.L3.81 (1.3.81 + thifensulfuron-m. (c56)) flufenacet (c123) c101 .c56.L3.81 c56.L3.81 (1.3.81 + thifensulfuron-m. (c56)) picolinafen (c101) c94.c56.L3.81 c56.L3.81 (1.3.81 + thifensulfuron-m. (c56)) Diflufenican (c94) c96.c56.L3.81 c56.L3.81 (1.3.81 + Thifensulfuron-m. (c56)) Beflubutamide (c96) c97.c56.L3.81 c56.L3.81 (1.3.81 + thifensulfuron-m. (c56)) Flurtamone (c97) c69.c56.L3.81 c56.L3.81 ( 1.3.81 + thifensulfuron-m. (C56)) isoproturon (c69) c64.c56.L3.81 c56.L3.81 (1.3.81 + thifensulfuron-m. (C56)) chlorotoluron (c64) c63.c56.L3 .81 c56.L3.81 (1.3.81 + thifensulfuron-m. (C56)) bromoxynil (c63) c68.c56.L3.81 c56.L3.81 (1.3.81 + thifensulfuron-m. (C56)) loxynil (c68) c1 16.c57.L3.81 c57.L3.81 (1.3.81 + tribenuron-m. (c57)) pendimethalin (c1 16) c132.c57.L3.81 c57.L3.81 (1.3.81 + Tribenuron-m. (C57)) pyroxasulfones (c132) c123.c57.L3.81 c57.L3.81 (1.3.81 + tribenuron-m. (C57)) flufenacet (c123) c101 .c57.L3.81 c57 .L3.81 (1.3.81 + tribenuron-m. (C57)) picolinafen (c101) c94.c57.L3.81 c57.L3.81 (1.3.81 + tribenuron-m. (C57)) diflufenican (c94) c96.c57.L3.81 c57.L3.81 (1.3.81 + tribenuron-m. (c57)) beflubutamide (c96) c97.c57.L3.81 c57.L3.81 (1.3.81 + tribenuron-m. (c57)) Flurtamone (c97) c69.c57.L3.81 c57.L3.81 (1.3.81 + tribenuron-m. (c57)) isoproturon (c69) c64.c57.L3.81 c57.L3.81 (1.3.81 + tribenuron-m. (c57)) Chlortoluron (c64) c63.c57.L3.81 c57.L3.81 (1.3.81 + tribenuron-m. (c57)) Bromoxynil (c63) c68.c57.L3.81 c57.L3.81 ( 1.3.81 + tribenuron-m. (C57)) loxynil (c68) c1 16.c59.L3.81 c59.L3.81 (1.3.81 + tritosulfuron (c59)) pendimethalin (c1 16) c132.c59.L3. 81 c59.L3.81 (1.3.81 + tritosulfuron (c59)) pyroxasulfones (c132) c123.c59.L3.81 c59.L3.81 (1.3.81 + tritosulfuron (c59)) flufenacet (c123) c101.c59. L3.81 c59.L3.81 (1.3.81 + tritosulfuron (c59)) picolinafen (c101) c94.c59.L3.81 c59.L3.81 (1.3.81 + tritosulfuron (c59)) diflufenican (c94) c96. c59.L3.81 c59.L3.81 (1.3.81 + tritosulfuron (c59)) Beflubutamide (c96) c97.c59.l.3.81 c59.L3.81 (1.3.81 + tritosulfuron (c59)) Flurtamone (c97) c69.c59.L3.81 c59.L3.81 (1.3.81 + tritosulfuron (c59)) isoproturon (c69) c64.c59.L3.81 c59.L3.81 (1.3.81 + tritosulfuron (c59)) chlortoluron ( c64) c63.c59.L3.81 c59.L3.81 (1.3.81 + Tri tosulfuron (c59)) Bromoxynil (c63) c68.c59.L3.81 c59.L3.81 (1.3.81 + tritosulfuron (c59)) loxynil (c68) c1 16.c25.L3.81 c25.L3.81 (1.3 .81 + orthosulfamuron (c25)) pendimethalin (c1 16) c132.c25.L3.81 c25.L3.81 (1.3.81 + orthosulfamuron (c25)) pyroxasulfones (c132) c123.c25.L3.81 c25.L3. 81 (1.3.81 + Orthosulfamuron (c25)) Flufenacet (c123) c101 .c25.L3.81 c25.L3.81 (1.3.81 + Orthosulfamuron (c25)) Picolinafen (c101) c94.c25.l.3.81 c25. L3.81 (1.3.81 + Orthosulfamuron (c25)) Diflufenican (c94) c96.c25.L3.81 c25.L3.81 (1.3.81 + Orthosulfamuron (c25)) Beflubutamide (c96) c97.c25.l.3.81 c25.L3.81 (1.3.81 + Orthosulfamuron (c25)) Flurtamone (c97) c69.c25.L3.81 c25.L3.81 (1.3.81 + Orthosulfamuron (c25)) Isoproturon (c69) c64.c25.l .3.81 c25.L3.81 (1.3.81 + orthosulfamuron (c25)) chlortoluron (c64) c63.c25.L3.81 c25.L3.81 (1.3.81 + orthosulfamuron (c25)) bromoxynil (c63) c68.c25 .L3.81 c25.L3.81 (1.3.81 + orthosulfamuron (c25)) loxynil (c68) c1 16.c50.L3.81 c50.L3.81 (1.3.81 + pyroxsulam (c50)) Pe ndimethalin (c1 16) c132.c50.L3.81 c50.L3.81 (1.3.81 + pyroxsulam (c50)) pyroxasulfones (c132) c123.c50.L3.81 c50.L3.81 (1.3.81 + pyroxsulam ( c50)) flufenacet (c123) c101 .c50.L3.81 c50.L3.81 (1.3.81 + pyroxsulam (c50)) picolinafen (c101) c94.c50.L3.81 c50.L3.81 (1.3.81 + Pyroxsulam (c50)) Diflufenican (c94) c96.c50.L3.81 c50.L3.81 (1.3.81 + pyroxsulam (c50)) Beflubutamide (c96) c97.c50.l.3.81 c50.L3.81 (1.3. 81 + pyroxsulam (c50)) flurtamone (c97) c69.c50.L3.81 c50.L3.81 (1.3.81 + pyroxsulam (c50)) isoproturon (c69) c64.c50.L3.81 c50.L3.81 ( 1.3.81 + pyroxsulam (c50)) chlortoluron (c64) c63.c50.L3.81 c50.L3.81 (1.3.81 + pyroxsulam (c50)) bromoxynil (c63) c68.c50.L3.81 c50.L3. 81 (1.3.81 + pyroxsulam (c50)) loxynil (c68) c1 16.c45.L3.81 c45.L3.81 (1.3.81 + penoxsulam (c45)) pendimethalin (c1 16) c132.c45.L3.81 c45.L3.81 (1.3.81 + penoxsulam (c45)) pyroxasulfones (c132) c123.c45.L3.81 c45.L3.81 (1.3.81 + penoxsulam (c45)) flufenacet (c123) c101 .c45.L3.81 c45.L3.81 (1.3.81 + penoxsulam (c45)) picolinafen (c101) c94.c45.L3.81 c45.L3.81 (1.3.81 + penoxsulam (c45)) diflufenican ( c94) c96.c45.L3.81 c45.L3.81 (1.3.81 + penoxsulam (c45)) beflubutamide (c96) c97.c45.L3.81 c45.L3.81 (1.3.81 + penoxsulam (c45)) Flurtamone (c97) c69.c45.L3.81 c45.L3.81 (1.3.81 + penoxsulam (c45)) isoproturon (c69) c64.c45.L3.81 c45.L3.81 (1.3.81 + penoxsulam (c45 )) Chlortoluron (c64) c63.c45.L3.81 c45.L3.81 (1.3.81 + Penoxsulam (c45)) Bromoxynil (c63) c68.c45.L3.81 c45.L3.81 (1.3.81 + Penoxsulam (c45)) loxynil (c68) c1 16.c27.L3.81 c27.L3.81 (1.3.81 + florasulam (c27)) pendimethalin (c1 16) c132.c27.L3.81 c27.L3.81 (1.3 .81 + florasulam (c27)) pyroxasulfones (c132) c123.c27.L3.81 c27.L3.81 (1.3.81 + florasulam (c27)) flufenacet (c123) c101 .c27.L3.81 c27.L3.81 (1.3.81 + florasulam (c27)) picolinafen (c101) c94.c27.l.3.81 c27.L3.81 (1.3.81 + florasulam (c27)) diflufenican (c94) c96.c27.L3.81 c27.L3 .81 (1.3.81 + florasulam (c27)) Beflubutamide (c96) c 97.c27.l.3.81 c27.L3.81 (1.3.81 + florasulam (c27)) flurtamone (c97) c69.c27.L3.81 c27.L3.81 (1.3.81 + florasulam (c27)) isoproturon ( c69) c64.c27.l.3.81 c27.L3.81 (1.3.81 + florasulam (c27)) chlorotoluron (c64) c63.c27.L3.81 c27.L3.81 (1.3.81 + florasulam (c27)) Bromoxynil (c63) c68.c27.L3.81 c27.L3.81 (1.3.81 + florasulam (c27)) loxynil (c68) c1 16.c46.L3.81 c46.L3.81 (1.3.81 + propoxy) carbazon (c46)) pendimethalin (c1 16) c132.c46.L3.81 c46.L3.81 (1.3.81 + propoxy-carbazone (c46)) pyroxasulfones (c132) c123.c46.L3.81 c46.L3.81 (1.3.81 + propoxy-carbazone (c46)) flufenacet (c123) c101 .c46.L3.81 c46.L3.81 (1.3.81 + propoxy-carbazone (c46)) picolinafen (c101) c94.c46.L3. 81 c46.L3.81 (1.3.81 + propoxy-carbazone (c46)) diflufenican (c94) c96.c46.L3.81 c46.L3.81 (1.3.81 + propoxy-carbazone (c46)) Beflubutamide (c96) c97.c46.L3.81 c46.L3.81 (1.3.81 + propoxy-carbazone (c46)) flurtamone (c97) c69.c46.L3.81 c46.L3.81 (1.3.81 + propoxy-carbazone (c46 )) Isoproturon (c69) c64.c46.L3.81 c46.L3.81 (1.3.8 1 + propoxy-carbazone (c46)) chlorotoluron (c64) c63.c46.L3.81 c46.L3.81 (1.3.81 + propoxy-carbazone (c46)) bromoxynil (c63) c68.c46.L3.81 c46. L3.81 (1.3.81 + propoxy-carbazone (c46)) loxynil (c68) c1 16.c28.L3.81 c28.L3.81 (1.3.81 + flucarbazone-s. (c28)) pendimethalin (c1 16) c132.c28.L3.81 c28.L3.81 (1.3.81 + flucarbazone-s. (c28)) pyroxasulfones (c132) c123.c28.L3.81 c28.L3.81 (1.3.81 + flucarbazone-s. (C28)) flufenacet (c123) c101 .c28.L3.81 c28.L3.81 (1.3.81 + flucarbazone-s. (C28)) picolinafen (c101) c94.c28. l.3.81 c28.L3.81 (1.3.81 + flucarbazone-s. (c28)) diflufenican (c94) c96.c28.L3.81 c28.L3.81 (1.3.81 + flucarbazone-s. (c28)) Beflubutamide (c96) c97.c28.l.3.81 c28.L3.81 (1.3.81 + flucarbazone-s. (C28)) Flurtamone (c97) c69.c28.L3.81 c28.L3.81 (1.3.81 + Flucarbazone-s. (C28)) isoproturon (c69) c64.c28.l.3.81 c28.L3.81 (1.3.81 + flucarbazone-s. (C28)) chlortoluron (c64) c63.c28.L3.81 c28. L3.81 (1.3.81 + flucarbazone-s. (C28)) bromoxynil (c63) c68.c28.L3.81 c28.L3.81 (1.3.81 + flucarbazone-s. (c28)) loxynil (c68) c1 16.c55.L3.81 c55.1.3.81 (1.3.81 + thiencarbazone-m (c55)) pendimethalin (c1 16) c132.c55.L3.81 c55.1.3.81 (1.3.81 + thiencarbazone-m. (c55)) pyroxasulfones (c132) c123.c55.L3.81 c55.1.3. 81 (1.3.81 + thiencarbazone-m. (C55)) flufenacet (c123) c101 .c55.L3.81 c55.1.3.81 (1.3.81 + thiencarbazone-m. (C55)) picolinafen (c101) c94.c55 .L3.81 c55.1.3.81 (1.3.81 + thiencarbazone-m. (C55)) diflufenican (c94) c96.c55.L3.81 c55.1.3.81 (1.3.81 + thiencarbazone-m. (C55) ) Beflubutamide (c96) c97.c55.L3.81 c55.1.3.81 (1.3.81 + Thiencarbazone-m. (C55)) Flurtamone (c97) c69.c55.L3.81 c55.1.3.81 (1.3.81 + Thiencarbazone-m. (C55)) isoproturon (c69) c64.c55.L3.81 c55.1.3.81 (1.3.81 + thiencarbazone-m. (C55)) chlorotoluron (c64) c63.c55.L3.81 c55 .1.3.81 (1.3.81 + thiencarbazone-m. (C55)) bromoxynil (c63) c68.c55.L3.81 c55.1.3.81 (1.3.81 + thiencarbazone-m. (C55)) loxynil (c68) c1 16.c33.L3.81 c33.L3.81 (1.3.81 + imazamox (c33)) pendimethalin (c1 16) c132.c33.l.3.81 c33.L3.81 (1.3.81 + imazamox (c33)) pyroxasulfones (c132) c123.c33.L3.81 c33.L3.81 (1.3.81 + imazamox (c33)) Flufenacet (c123) c101 .c33.L3.81 c33.L3.81 (1.3.81 + imazamox (c33)) picolinafen (c101) c94.c33.l.3.81 c33.L3.81 (1.3.81 + imazamox (c33 )) Diflufenican (c94) c96.c33.L3.81 c33.L3.81 (1.3.81 + Imazamox (c33)) Beflubutamide (c96) c97.c33.l.3.81 c33.L3.81 (1.3.81 + Imazamox (c33)) Flurtamone (c97) c69.c33.L3.81 c33.L3.81 (1.3.81 + imazamox (c33)) isoproturon (c69) c64.c33.l.3.81 c33.L3.81 (1.3.81 + Imazamox (c33)) chlorotoluron (c64) c63.c33.L3.81 c33.L3.81 (1.3.81 + imazamox (c33)) bromoxynil (c63) c68.c33.L3.81 c33.L3.81 (1.3 .81 + imazamox (c33)) loxynil (c68) c1 16.c32.L3.81 c32.L3.81 (1.3.81 + imazamethabenz-m. Pendimethalin (c1 16)
(c32)) (C32))
c132.c32.l.3.81 c32.L3.81 (1.3.81 + Imazamethabenz-m. Pyroxasulfone (c132)c132.c32.l.3.81 c32.L3.81 (1.3.81 + imazamethabenz-m, pyroxasulfones (c132)
(c32)) (C32))
c123.c32.L3.81 c32.L3.81 (1.3.81 + Imazamethabenz-m. Flufenacet (c123)c123.c32.L3.81 c32.L3.81 (1.3.81 + imazamethabenz-m, flufenacet (c123)
(c32)) (C32))
c101 .c32.L3.81 c32.L3.81 (1.3.81 + Imazamethabenz-m. Picolinafen (c101 )c101 .c32.L3.81 c32.L3.81 (1.3.81 + imazamethabenz-m, picolinafen (c101)
(c32)) (C32))
c94.c32.l.3.81 c32.L3.81 (1.3.81 + Imazamethabenz-m. Diflufenican (c94)c94.c32.l.3.81 c32.L3.81 (1.3.81 + imazamethabenz-m, diflufenican (c94)
(c32)) (C32))
c96.c32.L3.81 c32.L3.81 (1.3.81 + Imazamethabenz-m. Beflubutamid (c96)c96.c32.L3.81 c32.L3.81 (1.3.81 + imazamethabenz-m.beflubutamide (c96)
(c32)) (C32))
c97.c32.l.3.81 c32.L3.81 (1.3.81 + Imazamethabenz-m. Flurtamone (c97)c97.c32.l.3.81 c32.L3.81 (1.3.81 + imazamethabenz-m.flurtamone (c97)
(c32)) (C32))
c69.c32.L3.81 c32.L3.81 (1.3.81 + Imazamethabenz-m. Isoproturon (c69)c69.c32.L3.81 c32.L3.81 (1.3.81 + imazamethabenz-m, isoproturon (c69)
(c32)) (C32))
c64.c32.l.3.81 c32.L3.81 (1.3.81 + Imazamethabenz-m. Chlortoluron (c64)c64.c32.l.3.81 c32.L3.81 (1.3.81 + imazamethabenz-m, chlorotoluron (c64)
(c32)) c63.c32.L3.81 c32.L3.81 (1.3.81 + Imazamethabenz-m. Bromoxynil (c63) (c32))(C32)) c63.c32.L3.81 c32.L3.81 (1.3.81 + imazamethabenz-m, bromoxynil (c63) (c32))
c68.c32.L3.81 c32.L3.81 (1.3.81 + Imazamethabenz-m. loxynil (c68)c68.c32.L3.81 c32.L3.81 (1.3.81 + imazamethabenz-m-loxynil (c68)
(c32)) (C32))
c116.c149.L3.81 c149.L3.81 (1.3.81 + Flamprop (c149)) Pendimethalin (c116) c132.c149.1.3.81 c149.L3.81 (1.3.81 + Flamprop (c149)) Pyroxasulfone (c132)c116.c149.L3.81 c149.L3.81 (1.3.81 + Flamprop (c149)) pendimethalin (c116) c132.c149.1.3.81 c149.L3.81 (1.3.81 + Flamprop (c149)) pyroxasulfones ( c132)
C123.C149.1.3.81 c149.L3.81 (1.3.81 + Flamprop (c149)) Flufenacet (c123) c101.c149.L3.81 c149.L3.81 (1.3.81 + Flamprop (c149)) Picolinafen (c101) c94.c149.1.3.81 c149.L3.81 (1.3.81 + Flamprop (c149)) Diflufenican (c94) c96.c149.L3.81 c149.L3.81 (1.3.81 + Flamprop (c149)) Beflubutamid (c96) c97.c149.L3.81 c149.L3.81 (1.3.81 + Flamprop (c149)) Flurtamone (c97) c69.c149.L3.81 c149.L3.81 (1.3.81 + Flamprop (c149)) Isoproturon (c69) c64.c149.1.3.81 c149.L3.81 (1.3.81 + Flamprop (c149)) Chlortoluron (c64) c63.c149.L3.81 c149.L3.81 (1.3.81 + Flamprop (c149)) Bromoxynil (c63) c68.c149.L3.81 c149.L3.81 (1.3.81 + Flamprop (c149)) loxynil (c68) c116.c110.L3.81 d 10.1.3.81 (1.3.81 + Glyphosate-i. (c110)) Pendimethalin (c116) c132.c110.L3.81 d 10.1.3.81 (1.3.81 + Glyphosate-i. (c110)) Pyroxasulfone (c132) c123.c110.L3.81 d 10.1.3.81 (1.3.81 + Glyphosate-i. (c110)) Flufenacet (c123) c101.c110.L3.81 d 10.1.3.81 (1.3.81 + Glyphosate-i. (c110)) Picolinafen (c101) c94.c110.L3.81 d 10.1.3.81 (1.3.81 + Glyphosate-i. (c110)) Diflufenican (c94) c96.c110.L3.81 d 10.1.3.81 (1.3.81 + Glyphosate-i. (c110)) Beflubutamid (c96) c97.c110.1.3.81 d 10.1.3.81 (1.3.81 + Glyphosate-i. (c110)) Flurtamone (c97) c69.c110.L3.81 d 10.1.3.81 (1.3.81 + Glyphosate-i. (c110)) Isoproturon (c69) c64.c110.1.3.81 d 10.1.3.81 (1.3.81 + Glyphosate-i. (c110)) Chlortoluron (c64) c63.c110.L3.81 d 10.1.3.81 (1.3.81 + Glyphosate-i. (c110)) Bromoxynil (c63) c68.c110.1.3.81 d 10.1.3.81 (1.3.81 + Glyphosate-i. (c110)) loxynil (c68) c116.c111.L3.81 d 11.1.3.81 (1.3.81 + Glyphosate-t. (c111)) Pendimethalin (c116) c132.c111.l.3.81 d 11.1.3.81 (1.3.81 + Glyphosate-t. (c111)) Pyroxasulfone (c132) c123.c111.L3.81 d 11.1.3.81 (1.3.81 + Glyphosate-t. (c111)) Flufenacet (c123) c101.c111.L3.81 d 11.1.3.81 (1.3.81 + Glyphosate-t. (c111)) Picolinafen (c101) c94.c111.L3.81 d 11.1.3.81 (1.3.81 + Glyphosate-t. (c111)) Diflufenican (c94) c96.c111.L3.81 d 11.1.3.81 (1.3.81 + Glyphosate-t. (c111)) Beflubutamid (c96) c97.c111.L3.81 d 11.1.3.81 (1.3.81 + Glyphosate-t. (c111)) Flurtamone (c97) c69.c111.L3.81 d 11.1.3.81 (1.3.81 + Glyphosate-t. (c111)) Isoproturon (c69) c64.c111.L3.81 d 11.1.3.81 (1.3.81 + Glyphosate-t. (c111)) Chlortoluron (c64) c63.c111.L3.81 d 11.1.3.81 (1.3.81 + Glyphosate-t. (c111)) Bromoxynil (c63) c68.c111.L3.81 d 11.1.3.81 (1.3.81 + Glyphosate-t. (c111)) loxynil (c68) c116.c115.L3.81 d 15.1.3.81 (1.3.81 + Glufosinate-a. (d 15)) Pendimethalin (c116) c132.c115.L3.81 d 15.1.3.81 (1.3.81 + Glufosinate-a. (d 15)) Pyroxasulfone (c132) c123.c115.L3.81 d 15.1.3.81 (1.3.81 + Glufosinate-a. (d 15)) Flufenacet (c123) c101 .c1 15.L3.81 c1 15.L3.81 (1.3.81 + Glufosinate-a. (d 15)) Picolinafen (c101 ) c94.d 15.1.3.81 c1 15.L3.81 (1.3.81 + Glufosinate-a. (d 15)) Diflufenican (c94) c96.c1 15.L3.81 c1 15.L3.81 (1.3.81 + Glufosinate-a. (d 15)) Beflubutamid (c96) c97.c1 15.1.3.81 c1 15.L3.81 (1.3.81 + Glufosinate-a. (c1 15)) Flurtamone (c97) c69.c1 15.L3.81 c1 15.L3.81 (1.3.81 + Glufosinate-a. (d 15)) Isoproturon (c69) c64.c1 15.1.3.81 c1 15.L3.81 (1.3.81 + Glufosinate-a. (d 15)) Chlortoluron (c64) c63.c1 15.L3.81 c1 15.L3.81 (1.3.81 + Glufosinate-a. (d 15)) Bromoxynil (c63) c68.c1 15.1.3.81 c1 15.L3.81 (1.3.81 + Glufosinate-a. (d 15)) loxynil (c68)C123.C149.1.3.81 c149.L3.81 (1.3.81 + Flamprop (c149)) Flufenacet (c123) c101.c149.L3.81 c149.L3.81 (1.3.81 + Flamprop (c149)) Picolinafen ( c101) c94.c149.1.3.81 c149.L3.81 (1.3.81 + Flamprop (c149)) Diflufenican (c94) c96.c149.L3.81 c149.L3.81 (1.3.81 + Flamprop (c149)) Beflubutamide (c96) c97.c149.L3.81 c149.L3.81 (1.3.81 + Flamprop (c149)) Flurtamone (c97) c69.c149.L3.81 c149.L3.81 (1.3.81 + Flamprop (c149 )) Isoproturon (c69) c64.c149.1.3.81 c149.L3.81 (1.3.81 + Flamprop (c149)) Chlorotoluron (c64) c63.c149.L3.81 c149.L3.81 (1.3.81 + Flamprop (c149)) Bromoxynil (c63) c68.c149.L3.81 c149.L3.81 (1.3.81 + Flamprop (c149)) loxynil (c68) c116.c110.L3.81 d 10.1.3.81 (1.3.81 + Glyphosate-i (c110)) pendimethalin (c116) c132.c110.L3.81 d 10.1.3.81 (1.3.81 + glyphosate-i. (C110)) pyroxasulfones (c132) c123.c110.L3.81 d 10.1. 3.81 (1.3.81 + glyphosate-i. (C110)) flufenacet (c123) c101.c110.L3.81 d 10.1.3.81 (1.3.81 + glyphosate-i. (C110)) picolinafen (c101) c94.c110. L3.81 e 10.1.3.81 (1.3.81 + Eq yphosate-i. (c110)) Diflufenican (c94) c96.c110.L3.81 d 10.1.3.81 (1.3.81 + Glyphosate-i. (c110)) Beflubutamide (c96) c97.c110.1.3.81 e 10.1.3.81 (1.3. 81 + glyphosate-i. (C110)) flurtamone (c97) c69.c110.L3.81 d 10.1.3.81 (1.3.81 + glyphosate-i. (C110)) isoproturon (c69) c64.c110.1.3.81 d 10.1.3.81 (1.3.81 + glyphosate-i. (C110)) chlortoluron (c64) c63.c110.L3.81 d 10.1.3.81 (1.3.81 + glyphosate-i. (C110)) bromoxynil (c63) c68. c110.1.3.81 d 10.1.3.81 (1.3.81 + glyphosate-i. (c110)) loxynil (c68) c116.c111.L3.81 d 11.1.3.81 (1.3.81 + glyphosate-t. (c111)) Pendimethalin (c116) c132.c111.l.3.81 d 11.1.3.81 (1.3.81 + glyphosate-t. (C111)) pyroxasulfones (c132) c123.c111.L3.81 d 11.1.3.81 (1.3.81 + glyphosate- t (c111)) flufenacet (c123) c101.c111.L3.81 d 11.1.3.81 (1.3.81 + glyphosate-t. (c111)) picolinafen (c101) c94.c111.L3.81 d 11.1.3.81 ( 1.3.81 + glyphosate-t (c111)) diflufenican (c94) c96.c111.L3.81 d 11.1.3.81 (1.3.81 + glyphosate-t (c111)) beflubutamide (c96) c97.c111.L3. 81 d 11.1.3.81 (1.3.81 + Glyphosate-t. (c111)) Flurtamone (c97) c69.c111.L3.81 d 11.1.3.81 (1.3.81 + glyphosate-t. (c111)) isoproturon (c69) c64.c111.L3.81 d 11.1.3.81 (1.3. 81 + glyphosate-t (c111)) chlorotoluron (c64) c63.c111.L3.81 d 11.1.3.81 (1.3.81 + glyphosate-t (c111)) bromoxynil (c63) c68.c111.L3.81 d 11.1.3.81 (1.3.81 + glyphosate-t. (C111)) loxynil (c68) c116.c115.L3.81 d 15.1.3.81 (1.3.81 + glufosinate-a. (D 15)) pendimethalin (c116) c132 .c115.L3.81 d 15.1.3.81 (1.3.81 + glufosinate-a. (d 15)) pyroxasulfones (c132) c123.c115.L3.81 d 15.1.3.81 (1.3.81 + glufosinate-a. (d 15)) Flufenacet (c123) c101 .c1 15.L3.81 c1 15.L3.81 (1.3.81 + glufosinate-a. (d 15)) picolinafen (c101) c94.d 15.1.3.81 c1 15.L3.81 (1.3.81 + glufosinate -a. (d 15)) Diflufenican (c94) c96.c1 15.L3.81 c1 15.L3.81 (1.3.81 + Glufosinate-a. (d 15)) Beflubutamide (c96) c97.c1 15.1.3.81 c1 15.L3.81 (1.3.81 + glufosinate-a. (c1 15)) flurtamone (c97) c69.c1 15.L3.81 c1 15.L3.81 (1.3.81 + glufosinate-a. (d 15 )) Isoproturon (c69) c64.c1 15.1.3.81 c1 15.L3.81 (1.3.81 + glufosinate-a. (D 15)) chlorotoluron (c64) c63.c1 15.L3.81 c1 15.L3.81 (1.3.81 + glufosinate-a. (D 15)) bromoxynil (c63) c68.c1 15.1.3.81 c1 15.L3.81 (1.3.81 + glufosinate-a. (D 15)) loxynil (c68)
C1 16.C1 12.1.3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c1 12)) Pendimethalin (c1 16) c132.c1 12.l.3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c1 12)) Pyroxasulfone (c132) c123.c1 12.L3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c1 12)) Flufenacet (c123) c101 .c1 12.L3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c1 12)) Picolinafen (c101 ) c94.c1 12.1.3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c1 12)) Diflufenican (c94) c96.c1 12.L3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c1 12)) Beflubutamid (c96) c97.c1 12.1.3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c1 12)) Flurtamone (c97) c69.c1 12.L3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c1 12)) Isoproturon (c69) c64.c1 12.1.3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c1 12)) Chlortoluron (c64) c63.c1 12.L3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c1 12)) Bromoxynil (c63) c68.c1 12.1.3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c1 12)) loxynil (c68) c1 16.c132.L3.81 d 32.1.3.81 (1.3.81 + Pyroxasulfon (c132)) Pendimethalin (c1 16) c101 .c132.L3.81 d 32.1.3.81 (1.3.81 + Pyroxasulfon (c132)) Picolinafen (c101 ) c94.c132.1.3.81 d 32.1.3.81 (1.3.81 + Pyroxasulfon (c132)) Diflufenican (c94) c96.c132.1.3.81 d 32.1.3.81 (1.3.81 + Pyroxasulfon (c132)) Beflubutamid (c96) c69.c132.L3.81 d 32.1.3.81 (1.3.81 + Pyroxasulfon (c132)) Isoproturon (c69) c64.c132.1.3.81 d 32.1.3.81 (1.3.81 + Pyroxasulfon (c132)) Chlortoluron (c64) c63.c132.1.3.81 d 32.1.3.81 (1.3.81 + Pyroxasulfon (c132)) Bromoxynil (c63) c68.c132.1.3.81 d 32.1.3.81 (1.3.81 + Pyroxasulfon (c132)) loxynil (c68) c1 16.c123.L3.81 c123.L3.81 (1.3.81 + Flufenacet (c123)) Pendimethalin (c1 16) c101 .c123.L3.81 c123.L3.81 (1.3.81 + Flufenacet (d 23)) Picolinafen (c101 ) c94.c123.L3.81 c123.L3.81 (1.3.81 + Flufenacet (d 23)) Diflufenican (c94) c96.c123.L3.81 c123.L3.81 (1.3.81 + Flufenacet (d 23)) Beflubutamid (c96) c69.c123.L3.81 c123.L3.81 (1.3.81 + Flufenacet (d 23)) Isoproturon (c69) c64.c123.L3.81 c123.L3.81 (1.3.81 + Flufenacet (d 23)) Chlortoluron (c64) c63.c123.L3.81 c123.L3.81 (1.3.81 + Flufenacet (d 23)) Bromoxynil (c63) c68.c123.L3.81 c123.L3.81 (1.3.81 + Flufenacet (d 23)) loxynil (c68) c1 16.c16.L3.81 c16.L3.81 (1.3.81 + Prosulfocarb (c16)) Pendimethalin (c1 16) c101 .c16.L3.81 c16.L3.81 (1.3.81 + Prosulfocarb (c16)) Picolinafen (c101 ) c94.c16.L3.81 c16.L3.81 (1.3.81 + Prosulfocarb (c16)) Diflufenican (c94) c96.c16.L3.81 c16.L3.81 (1.3.81 + Prosulfocarb (c16)) Beflubutamid (c96) c69.c16.1.3.81 c16.L3.81 (1.3.81 + Prosulfocarb (c16)) Isoproturon (c69) c64.c16.l.3.81 c16.L3.81 (1.3.81 + Prosulfocarb (c16)) Chlortoluron (c64) c63.c16.L3.81 c16.L3.81 (1.3.81 + Prosulfocarb (c16)) Bromoxynil (c63) c68.c16.L3.81 c16.L3.81 (1.3.81 + Prosulfocarb (c16)) loxynil (c68) c101 .c1 16.L3.81 d 16.1.3.81 (1.3.81 + Pendimethalin (c1 16)) Picolinafen (c101 ) c94.c1 16.L3.81 d 16.1.3.81 (1.3.81 + Pendimethalin (c1 16)) Diflufenican (c94) c96.c1 16.L3.81 d 16.1.3.81 (1.3.81 + Pendimethalin (c1 16)) Beflubutamid (c96) c69.c1 16.L3.81 d 16.1.3.81 (1.3.81 + Pendimethalin (c1 16)) Isoproturon (c69) c64.d 16.1.3.81 d 16.1.3.81 (1.3.81 + Pendimethalin (c1 16)) Chlortoluron (c64) c63.c1 16.L3.81 d 16.1.3.81 (1.3.81 + Pendimethalin (c1 16)) Bromoxynil (c63) c68.c1 16.L3.81 d 16.1.3.81 (1.3.81 + Pendimethalin (c1 16)) loxynil (c68) c69.c133.L3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) Isoproturon (c69) c64.c133.1.3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) Chlortoluron (c64) c63.c133.1.3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) Bromoxynil (c63) c68.c133.1.3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) loxynil (c68) c59.c133.1.3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) Tritosulfuron (c59) c27.c133.1.3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) Florasulam (c27) c57.c133.1.3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) Tribenuron (c57) c39.c133.1.3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) lodosulfuron (c39) c42.c133.1.3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) Metsulfuron-m. (c42) c69.c138.L3.81 c138.L3.81 (1.3.81 + MCPA (c138)) Isoproturon (c69) c64.c138.1.3.81 c138.L3.81 (1.3.81 + MCPA (c138)) Chlortoluron (c64) c63.c138.1.3.81 c138.L3.81 (1.3.81 + MCPA (c138)) Bromoxynil (c63) c68.c138.1.3.81 c138.L3.81 (1.3.81 + MCPA (c138)) loxynil (c68) c59.c138.L3.81 c138.L3.81 (1.3.81 + MCPA (c138)) Tritosulfuron (c59) c27.c138.1.3.81 c138.L3.81 (1.3.81 + MCPA (c138)) Florasulam (c27) c57.c138.L3.81 c138.L3.81 (1.3.81 + MCPA (c138)) Tribenuron (c57) c39.c138.1.3.81 c138.L3.81 (1.3.81 + MCPA (c138)) lodosulfuron (c39) c42.c138.1.3.81 c138.L3.81 (1.3.81 + MCPA (c138)) Metsulfuron-m. (c42) c69.c150.1.3.81 c150.L3.81 (1.3.81 + 2,4-DP (c150)) Isoproturon (c69) c64.c150.1.3.81 c150.L3.81 (1.3.81 + 2,4-DP (c150)) Chlortoluron (c64) c63.c150.1.3.81 c150.L3.81 (1.3.81 + 2,4-DP (c150)) Bromoxynil (c63) c68.c150.1.3.81 c150.L3.81 (1.3.81 + 2,4-DP (c150)) loxynil (c68) c59.c150.1.3.81 c150.L3.81 (1.3.81 + 2,4-DP (c150)) Tritosulfuron (c59) c27.c150.1.3.81 c150.L3.81 (1.3.81 + 2,4-DP (c150)) Florasulam (c27) c57.c150.1.3.81 c150.L3.81 (1.3.81 + 2,4-DP (c150)) Tribenuron (c57) c39.c150.1.3.81 c150.L3.81 (1.3.81 + 2,4-DP (c150)) lodosulfuron (c39) c42.c150.1.3.81 c150.L3.81 (1.3.81 + 2,4-DP (c150)) Metsulfuron-m. (c42) c69.c70.L3.81 c70.L3.81 (1.3.81 + CMPP-P (c70)) Isoproturon (c69) c64.c70.L3.81 c70.L3.81 (1.3.81 + CMPP-P (c70)) Chlortoluron (c64) c63.c70.L3.81 c70.L3.81 (1.3.81 + CMPP-P (c70)) Bromoxynil (c63) c68.c70.L3.81 c70.L3.81 (1.3.81 + CMPP-P (c70)) loxynil (c68) c59.c70.L3.81 c70.L3.81 (1.3.81 + CMPP-P (c70)) Tritosulfuron (c59) c27.c70.l.3.81 c70.L3.81 (1.3.81 + CMPP-P (c70)) Florasulam (c27) c57.c70.L3.81 c70.L3.81 (1.3.81 + CMPP-P (c70)) Tribenuron (c57) c39.c70.L3.81 c70.L3.81 (1.3.81 + CMPP-P (c70)) lodosulfuron (c39) c42.c70.L3.81 c70.L3.81 (1.3.81 + CMPP-P (c70)) Metsulfuron-m. (c42) c69.c136.L3.81 c136.L3.81 (1.3.81 + Dicamba (c136)) Isoproturon (c69) c64.c136.1.3.81 c136.L3.81 (1.3.81 + Dicamba (c136)) Chlortoluron (c64) c63.c136.1.3.81 c136.L3.81 (1.3.81 + Dicamba (c136)) Bromoxynil (c63) c68.c136.1.3.81 c136.L3.81 (1.3.81 + Dicamba (c136)) loxynil (c68) c59.c136.L3.81 c136.L3.81 (1.3.81 + Dicamba (c136)) Tritosulfuron (c59) c27.c136.1.3.81 c136.L3.81 (1.3.81 + Dicamba (c136)) Florasulam (c27) c57.c136.L3.81 c136.L3.81 (1.3.81 + Dicamba (c136)) Tribenuron (c57) c39.c136.1.3.81 c136.L3.81 (1.3.81 + Dicamba (c136)) lodosulfuron (c39) c42.c136.1.3.81 c136.L3.81 (1.3.81 + Dicamba (c136)) Metsulfuron-m. (c42) c69.c134.L3.81 c134.L3.81 (1.3.81 + Aminopyralid (c134)) Isoproturon (c69) c64.c134.1.3.81 c134.L3.81 (1.3.81 + Aminopyralid (c134)) Chlortoluron (c64) c63.c134.1.3.81 c134.L3.81 (1.3.81 + Aminopyralid (c134)) Bromoxynil (c63) c68.c134.1.3.81 c134.L3.81 (1.3.81 + Aminopyralid (c134)) loxynil (c68) c59.c134.1.3.81 c134.L3.81 (1.3.81 + Aminopyralid (c134)) Tritosulfuron (c59) c27.c134.1.3.81 c134.L3.81 (1.3.81 + Aminopyralid (c134)) Florasulam (c27) c57.c134.1.3.81 c134.L3.81 (1.3.81 + Aminopyralid (c134)) Tribenuron (c57) c39.c134.1.3.81 c134.L3.81 (1.3.81 + Aminopyralid (c134)) lodosulfuron (c39) c42.c134.1.3.81 c134.L3.81 (1.3.81 + Aminopyralid (c134)) Metsulfuron-m. (c42) c69.c135.1.3.81 d 35.1.3.81 (1.3.81 + Clopyralid (c135)) Isoproturon (c69) c64.c135.1.3.81 d 35.1.3.81 (1.3.81 + Clopyralid (c135)) Chlortoluron (c64) c63.c135.1.3.81 d 35.1.3.81 (1.3.81 + Clopyralid (c135)) Bromoxynil (c63) c68.c135.1.3.81 d 35.1.3.81 (1.3.81 + Clopyralid (c135)) loxynil (c68) c59.c135.L3.81 d 35.1.3.81 (1.3.81 + Clopyralid (c135)) Tritosulfuron (c59) c27.c135.1.3.81 d 35.1.3.81 (1.3.81 + Clopyralid (c135)) Florasulam (c27) c57.c135.L3.81 d 35.1.3.81 (1.3.81 + Clopyralid (c135)) Tribenuron (c57) c39.c135.1.3.81 d 35.1.3.81 (1.3.81 + Clopyralid (c135)) lodosulfuron (c39) c42.c135.1.3.81 d 35.1.3.81 (1.3.81 + Clopyralid (c135)) Metsulfuron-m. (c42) c69.c137.L3.81 d 37.1.3.81 (1.3.81 + Fluroxypyr-m. (c137)) Isoproturon (c69) c64.c137.1.3.81 d 37.1.3.81 (1.3.81 + Fluroxypyr-m. (c137)) Chlortoluron (c64) c63.c137.1.3.81 d 37.1.3.81 (1.3.81 + Fluroxypyr-m. (c137)) Bromoxynil (c63) c68.c137.1.3.81 d 37.1.3.81 (1.3.81 + Fluroxypyr-m. (c137)) loxynil (c68) c59.c137.L3.81 d 37.1.3.81 (1.3.81 + Fluroxypyr-m. (c137)) Tritosulfuron (c59) c27.c137.1.3.81 d 37.1.3.81 (1.3.81 + Fluroxypyr-m. (c137)) Florasulam (c27) c57.c137.L3.81 d 37.1.3.81 (1.3.81 + Fluroxypyr-m. (c137)) Tribenuron (c57) c39.c137.L3.81 d 37.1.3.81 (1.3.81 + Fluroxypyr-m. (c137)) lodosulfuron (c39) c42.c137.1.3.81 d 37.1.3.81 (1.3.81 + Fluroxypyr-m. (c137)) Metsulfuron-m. (c42) c69.c141.L3.81 c141 .1.3.81 (1.3.81 + Aminocyclopyrachlor Isoproturon (c69)C1 16.C1 12.1.3.81 d 12.1.3.81 (1.3.81 + bialaphos (c1 12)) pendimethalin (c1 16) c132.c1 12.l.3.81 d 12.1.3.81 (1.3.81 + bialaphos (c1 12)) Pyroxasulfones (c132) c123.c1 12.L3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c1 12)) Flufenacet (c123) c101 .c1 12.L3.81 d 12.1.3.81 (1.3.81 + Bialaphos ( c1 12)) Picolinafen (c101) c94.c1 12.1.3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c1 12)) Diflufenican (c94) c96.c1 12.L3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c1 12)) Beflubutamide (c96) c97.c1 12.1.3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c1 12)) Flurtamone (c97) c69.c1 12.L3.81 d 12.1.3.81 (1.3. 81 + bialaphos (c1 12)) isoproturon (c69) c64.c1 12.1.3.81 d 12.1.3.81 (1.3.81 + bialaphos (c1 12)) chlorotoluron (c64) c63.c1 12.L3.81 d 12.1.3.81 ( 1.3.81 + Bialaphos (c1 12)) Bromoxynil (c63) c68.c1 12.1.3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c1 12)) loxynil (c68) c1 16.c132.L3.81 d 32.1. 3.81 (1.3.81 + pyroxasulfone (c132)) pendimethalin (c1 16) c101 .c132.L3.81 d 32.1.3.81 (1.3.81 + pyroxasulfone (c132)) picolinafen (c1 01) c94.c132.1.3.81 d 32.1.3.81 (1.3.81 + pyroxasulfone (c132)) diflufenican (c94) c96.c132.1.3.81 d 32.1.3.81 (1.3.81 + pyroxasulfone (c132)) Beflubutamide ( c96) c69.c132.L3.81 d 32.1.3.81 (1.3.81 + pyroxasulfone (c132)) isoproturon (c69) c64.c132.1.3.81 d 32.1.3.81 (1.3.81 + pyroxasulfone (c132)) chlorotoluron ( c64) c63.c132.1.3.81 d 32.1.3.81 (1.3.81 + pyroxasulfone (c132)) bromoxynil (c63) c68.c132.1.3.81 d 32.1.3.81 (1.3.81 + pyroxasulfone (c132)) loxynil ( c68) c1 16.c123.L3.81 c123.L3.81 (1.3.81 + flufenacet (c123)) pendimethalin (c1 16) c101 .c123.L3.81 c123.L3.81 (1.3.81 + flufenacet (d 23)) picolinafen (c101) c94.c123.L3.81 c123.L3.81 (1.3.81 + flufenacet (d23)) diflufenican (c94) c96.c123.L3.81 c123.L3.81 (1.3.81 + Flufenacet (d 23)) beflubutamide (c96) c69.c123.L3.81 c123.L3.81 (1.3.81 + flufenacet (d 23)) isoproturon (c69) c64.c123.L3.81 c123.L3.81 (1.3.81 + flufenacet (d 23)) chlortoluron (c64) c63.c123.L3.81 c123.L3.81 (1.3.81 + flufenacet (d 23)) bromoxynil (c63) c68.c123.L3.8 1 c123.L3.81 (1.3.81 + flufenacet (d23)) loxynil (c68) c1 16.c16.L3.81 c16.L3.81 (1.3.81 + prosulfocarb (c16)) pendimethalin (c1 16) c101 .c16.L3.81 c16.L3.81 (1.3.81 + prosulfocarb (c16)) picolinafen (c101) c94.c16.L3.81 c16.L3.81 (1.3.81 + prosulfocarb (c16)) diflufenican (c94 ) c96.c16.L3.81 c16.L3.81 (1.3.81 + prosulfocarb (c16)) beflubutamide (c96) c69.c16.1.3.81 c16.L3.81 (1.3.81 + prosulfocarb (c16)) isoproturon (c69) c64.c16.l.3.81 c16.L3.81 (1.3.81 + prosulfocarb (c16)) chlorotoluron (c64) c63.c16.L3.81 c16.L3.81 (1.3.81 + prosulfocarb (c16)) bromoxynil ( c63) c68.c16.L3.81 c16.L3.81 (1.3.81 + prosulfocarb (c16)) loxynil (c68) c101 .c1 16.L3.81 d 16.1.3.81 (1.3.81 + pendimethalin (c1 16) ) Picolinafen (c101) c94.c1 16.L3.81 d 16.1.3.81 (1.3.81 + pendimethalin (c1 16)) diflufenican (c94) c96.c1 16.L3.81 d 16.1.3.81 (1.3.81 + pendimethalin (c1 16)) Beflubutamide (c96) c69.c1 16.L3.81 d 16.1.3.81 (1.3.81 + pendimethalin (c1 16)) isoproturon (c69) c64.d 16.1.3.81 d 16.1.3.81 (1.3.81 + Pendimethalin (c1 16)) chlorotoluron (c64) c63.c1 16.L3.81 d 16.1.3.81 (1.3.81 + pendimethalin (c1 16)) bromoxynil (c63) c68.c1 16.L3.81 d 16.1.3.81 (1.3.81 + pendimethalin (c1 16)) loxynil (c68) c69.c133.L3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) isoproturon (c69) c64.c133.1.3 .81 c133.L3.81 (1.3.81 + 2,4-D (c133)) chlorotoluron (c64) c63.c133.1.3.81 c133.L3.81 (1.3.81 + 2,4-D (c133) ) Bromoxynil (c63) c68.c133.1.3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) loxynil (c68) c59.c133.1.3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) tritosulfuron (c59) c27. c133.1.3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) florasulam (c27) c57.c133.1.3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) tribenuron (c57) c39.c133.1.3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) lodosulfuron (c39) c42.c133.1.3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) metsulfuron-m. (c42) c69.c138.L3.81 c138.L3.81 (1.3.81 + MCPA (c138)) isoproturon (c69) c64.c138.1.3.81 c138.L3.81 (1.3.81 + MCPA (c138) ) Chlorotoluron (c64) c63.c138.1.3.81 c138.L3.81 (1.3.81 + MCPA (c138)) Bromoxynil (c63) c68.c138.1.3.81 c138.L3.81 (1.3.81 + MCPA ( c138)) loxynil (c68) c59.c138.L3.81 c138.L3.81 (1.3.81 + MCPA (c138)) tritosulfuron (c59) c27.c138.1.3.81 c138.L3.81 (1.3.81 + MCPA (c138)) florasulam (c27) c57.c138.L3.81 c138.L3.81 (1.3.81 + MCPA (c138)) tribenuron (c57) c39.c138.1.3.81 c138.L3.81 (1.3. 81 + MCPA (c138)) lodosulfuron (c39) c42.c138.1.3.81 c138.L3.81 (1.3.81 + MCPA (c138)) metsulfuron-m. (c42) c69.c150.1.3.81 c150.L3.81 (1.3.81 + 2,4-DP (c150)) isoproturon (c69) c64.c150.1.3.81 c150.L3.81 (1.3.81 + 2,4-DP (c150)) Chlorotoluron (c64) c63.c150.1.3.81 c150.L3.81 (1.3.81 + 2,4-DP (c150)) Bromoxynil (c63) c68.c150.1.3.81 c150.L3.81 (1.3.81 + 2,4-DP (c150)) loxynil (c68) c59.c150.1.3.81 c150.L3.81 (1.3.81 + 2,4-DP (c150)) tritosulfuron (c59) c27.c150.1.3.81 c150.L3.81 (1.3.81 + 2.4-DP (c150)) florasulam (c27) c57.c150.1.3.81 c150.L3.81 (1.3.81 + 2,4-DP (c150)) tribenuron (c57) c39.c150.1.3.81 c150.L3.81 (1.3.81 + 2,4-DP (c150)) iodosulfuron (c39) c42.c150.1.3.81 c150.L3.81 (1.3.81 + 2.4-DP (c150)) metsulfuron-m. (c42) c69.c70.L3.81 c70.L3.81 (1.3.81 + CMPP-P (c70)) isoproturon (c69) c64.c70.L3.81 c70.L3.81 (1.3.81 + CMPP- P (c70)) Chlortoluron (c64) c63.c70.L3.81 c70.L3.81 (1.3.81 + CMPP-P (c70)) Bromoxynil (c63) c68.c70.L3.81 c70.L3.81 (1.3.81 + CMPP-P (c70)) loxynil (c68) c59.c70.L3.81 c70.L3.81 (1.3.81 + CMPP-P (c70 )) Tritosulfuron (c59) c27.c70.l.3.81 c70.L3.81 (1.3.81 + CMPP-P (c70)) florasulam (c27) c57.c70.L3.81 c70.L3.81 (1.3.81 + CMPP-P (c70)) tribenuron (c57) c39.c70.L3.81 c70.L3.81 (1.3.81 + CMPP-P (c70)) lodosulfuron (c39) c42.c70.L3.81 c70.L3 .81 (1.3.81 + CMPP-P (c70)) metsulfuron-m. (c42) c69.c136.L3.81 c136.L3.81 (1.3.81 + dicamba (c136)) isoproturon (c69) c64.c136.1.3.81 c136.L3.81 (1.3.81 + dicamba (c136) ) Chlorotoluron (c64) c63.c136.1.3.81 c136.L3.81 (1.3.81 + Dicamba (c136)) Bromoxynil (c63) c68.c136.1.3.81 c136.L3.81 (1.3.81 + Dicamba ( c136)) loxynil (c68) c59.c136.L3.81 c136.L3.81 (1.3.81 + Dicamba (c136)) tritosulfuron (c59) c27.c136.1.3.81 c136.L3.81 (1.3.81 + Dicamba (c136)) florasulam (c27) c57.c136.L3.81 c136.L3.81 (1.3.81 + dicamba (c136)) tribenuron (c57) c39.c136.1.3.81 c136.L3.81 (1.3. 81 + Dicamba (c136)) lodosulfuron (c39) c42.c136.1.3.81 c136.L3.81 (1.3.81 + dicamba (c136)) metsulfuron-m. (c42) c69.c134.L3.81 c134.L3.81 (1.3.81 + aminopyralid (c134)) isoproturon (c69) c64.c134.1.3.81 c134.L3.81 (1.3.81 + aminopyralid (c134) ) Chlorotoluron (c64) c63.c134.1.3.81 c134.L3.81 (1.3.81 + aminopyralid (c134)) bromoxynil (c63) c68.c134.1.3.81 c134.L3.81 (1.3.81 + aminopyralid ( c134)) loxynil (c68) c59.c134.1.3.81 c134.L3.81 (1.3.81 + aminopyralid (c134)) tritosulfuron (c59) c27.c134.1.3.81 c134.L3.81 (1.3.81 + Aminopyralid (c134)) florasulam (c27) c57.c134.1.3.81 c134.L3.81 (1.3.81 + aminopyralid (c134)) tribenuron (c57) c39.c134.1.3.81 c134.L3.81 (1.3. 81 + aminopyralid (c134)) iodosulfuron (c39) c42.c134.1.3.81 c134.L3.81 (1.3.81 + aminopyralid (c134)) metsulfuron-m. (c42) c69.c135.1.3.81 d 35.1.3.81 (1.3.81 + clopyralid (c135)) isoproturon (c69) c64.c135.1.3.81 d 35.1.3.81 (1.3.81 + clopyralid (c135)) chlortoluron (c64) c63.c135.1.3.81 d 35.1.3.81 (1.3.81 + clopyralid (c135)) bromoxynil (c63) c68.c135.1.3.81 d 35.1.3.81 (1.3.81 + clopyralid (c135)) loxynil (c68) c59.c135.L3.81 d 35.1.3.81 (1.3.81 + clopyralid (c135)) tritosulfuron (c59) c27.c135.1.3.81 d 35.1.3.81 (1.3.81 + clopyralid (c135)) florasulam (c27) c57.c135.L3.81 d 35.1.3.81 (1.3.81 + clopyralid (c135)) tribenuron (c57) c39.c135.1.3.81 d 35.1.3.81 (1.3.81 + clopyralid (c135)) iodosulfuron (c39) c42.c135.1.3.81 d 35.1.3.81 (1.3.81 + clopyralid (c135)) metsulfuron-m. (c42) c69.c137.L3.81 d 37.1.3.81 (1.3.81 + fluroxypyr-m. (c137)) isoproturon (c69) c64.c137.1.3.81 d 37.1.3.81 (1.3.81 + fluroxypyr-m (c137)) Chlortoluron (c64) c63.c137.1.3.81 d 37.1.3.81 (1.3.81 + Fluroxypyr-m. (c137)) Bromoxynil (c63) c68.c137.1.3.81 d 37.1.3.81 (1.3 .81 + fluroxypyr-m. (C137)) loxynil (c68) c59.c137.L3.81 d 37.1.3.81 (1.3.81 + fluroxypyr-m. (C137)) tritosulfuron (c59) c27.c137.1.3.81 d 37.1.3.81 (1.3.81 + fluroxypyr-m. (c137)) florasulam (c27) c57.c137.L3.81 d 37.1.3.81 (1.3.81 + fluroxypyr-m. (c137)) tribenuron (c57) c39.c137.L3.81 d 37.1.3.81 (1.3.81 + fluroxypyr-m. (c137)) lodosulfuron (c39) c42.c137.1.3.81 d 37.1.3.81 (1.3.81 + fluroxypyr-m. (c137 )) Metsulfuron-m. (c42) c69.c141.L3.81 c141 .1.3.81 (1.3.81 + aminocyclopyrachlor isoproturon (c69)
(c141 )) (c141))
c64.c141 .1.3.81 c141 .1.3.81 (1.3.81 + Aminocyclopyrachlor Chlortoluron (c64)c64.c141 .1.3.81 c141 .1.3.81 (1.3.81 + aminocyclopyrachloro chlorotoluron (c64)
(c141 )) (c141))
c63.c141 .L3.81 c141 .1.3.81 (1.3.81 + Aminocyclopyrachlor Bromoxynil (c63)c63.c141 .L3.81 c141 .1.3.81 (1.3.81 + aminocyclopyrachlor Bromoxynil (c63)
(c141 )) (c141))
C68.C141 .1.3.81 c141 .1.3.81 (1.3.81 + Aminocyclopyrachlor loxynil (c68) C68.C141 .1.3.81 c141 .1.3.81 (1.3.81 + aminocyclopyrachloro loxynil (c68)
(c141 )) (c141))
C59.C141 .1.3.81 c141 .1.3.81 (1.3.81 + Aminocyclopyrachlor Tritosulfuron (c59) C59.C141 .1.3.81 c141 .1.3.81 (1.3.81 + aminocyclopyrachloro tritosulfuron (c59)
(c141 )) (c141))
c27.c141 .1.3.81 c141 .1.3.81 (1.3.81 + Aminocyclopyrachlor Florasulam (c27)c27.c141 .1.3.81 c141 .1.3.81 (1.3.81 + aminocyclopyrachlorofluasulam (c27)
(c141 )) (c141))
c57.c141 .1.3.81 c141 .1.3.81 (1.3.81 + Aminocyclopyrachlor Tribenuron (c57)c57.c141 .1.3.81 c141 .1.3.81 (1.3.81 + aminocyclopyrachloro tribenuron (c57)
(c141 )) (c141))
c39.c141 .L3.81 c141 .1.3.81 (1.3.81 + Aminocyclopyrachlor lodosulfuron (c39)c39.c141 .L3.81 c141 .1.3.81 (1.3.81 + aminocyclopyrachloro-iodosulfuron (c39)
(c141 )) (c141))
c42.c141 .1.3.81 c141 .1.3.81 (1.3.81 + Aminocyclopyrachlor Metsulfuron-m. (c42)c42.c141 .1.3.81 c141 .1.3.81 (1.3.81 + aminocyclopyrachlor metsulfuron-m. (c42)
(c141 )) (c141))
Tabelle 36: In einer bevorzugten Ausgestaltungsform der Erfindung enthalten die Mischungen gemäß Tabelle 35 jeweils zusätzlich eine Komponente B, ausgewählt aus der Gruppe Cloquintocet, Mefenpyr, Fenchlorazol, Isoxadifen, und Cyprosulfamid.Table 36: In a preferred embodiment of the invention, the mixtures according to Table 35 each additionally contain a component B selected from the group cloquintocet, mefenpyr, fenchlorazole, isoxadifen, and cyprosulfamide.
Tabelle 37: In einer besonders bevorzugten Ausgestaltungsform der Erfindung enthalten die Mischungen gemäß Tabelle 35 jeweils zusätzlich als Komponente B Cloquintocet (B2). Tabelle 38: In einer weiteren besonders bevorzugten Ausgestaltungsform der Erfindung enthalten die Mischungen gemäß Tabelle 35 jeweils zusätzlich als Komponente B Mefenpyr (B14).Table 37: In a particularly preferred embodiment of the invention, the mixtures according to Table 35 each additionally contain, as component B, cloquintocet (B2). Table 38: In a further particularly preferred embodiment of the invention, the mixtures according to Table 35 each additionally contain, as component B, Mefenpyr (B14).
Tabelle 39: In einer weiteren besonders bevorzugten Ausgestaltungsform der Erfin- dung enthalten die Mischungen gemäß Tabelle 35 jeweils zusätzlich als Komponente B Isoxadifen (B13).Table 39: In a further particularly preferred embodiment of the invention, the mixtures according to Table 35 additionally contain, as component B, isoxadifen (B13).
Tabelle 40: Ein weiterer bevorzugter Gegenstand der vorliegenden Erfindung sind Mischungen, die sich von den Mischungen gemäß den Tabellen 35 bis 39, dadurch unterscheiden, dass sie als Komponente A) der Mischung das Benzoylpyrazol der Formel 1.1.81 , dass heißt die Verbindung der Formel I mit R1 Methyl;Table 40: Another preferred subject matter of the present invention are mixtures which differ from the mixtures according to Tables 35 to 39 in that as component A) of the mixture, the benzoylpyrazole of the formula 1.1.81, that is the compound of the formula I with R1 is methyl;
R2 Methyl;R2 is methyl;
R3 Methylsulfonyl;R3 is methylsulfonyl;
R4 Wasserstoff;R4 is hydrogen;
R5 Ethyl;R5 is ethyl;
R6 Wasserstoff; oder dessen landwirtschaftlich geeignetes Salz, enthalten.R6 is hydrogen; or its agriculturally suitable salt.
Die Mischungen gemäß den Tabellen 35 bis 40 eignen sich insbesondere für die Bekämpfung von Schadpflanzen in Getreidekulturen, wie beispielsweise Weizen, Rog- gen, Hafer, Gerste und Triticale.The mixtures according to Tables 35 to 40 are particularly suitable for combating harmful plants in cereal crops, such as wheat, rye, oats, barley and triticale.
Ebenfalls besonders bevorzugt sind Mischungen gemäß der folgenden Tabelle 41 , enthaltend als Komponente A) die Verbindung der Formel 1.3.81 , dass heißt das Ben- zoylpyrazol der Formel I mitLikewise particularly preferred are mixtures according to the following Table 41, containing as component A) the compound of the formula 1.3.81, that is to say the benzoylpyrazole of the formula I ## STR4 ## with
R1 Methyl;R1 is methyl;
R2 Methyl;R2 is methyl;
R3 Methylsulfonyl;R3 is methylsulfonyl;
R4 Prop-2-inyl;R4 is prop-2-ynyl;
R5 Ethyl;R5 is ethyl;
R6 Wasserstoff;R6 is hydrogen;
und zwei weitere Herbizide C, Ca und Cb, ausgewählt aus den Herbiziden gemäß Tabelle 34, d -c150:and two further herbicides C, Ca and Cb selected from the herbicides according to Table 34, d -c150:
Tabelle 41 :Table 41:
Mischung: 1.3.81 + O CbMixture: 1.3.81 + OCb
c61.c31.L3.81 c31 .L3.81 (1.3.81 + Foramsulfuron (c31 )) Atrazin (c61 ) c77.c31.1.3.81 c31 .L3.81 (1.3.81 + Foramsulfuron (c31 )) Terbuthylazin (c77)c61.c31.L3.81 c31 .L3.81 (1.3.81 + foramsulfuron (c31)) atrazine (c61) c77.c31.1.3.81 c31 .L3.81 (1.3.81 + foramsulfuron (c31)) terbuthylazine ( c77)
C63.C31.1.3.81 c31 .L3.81 (1.3.81 + Foramsulfuron (c31 )) Bromoxynil (c63)C63.C31.1.3.81 c31 .L3.81 (1.3.81 + foramsulfuron (c31)) Bromoxynil (c63)
C75.C31.1.3.81 c31 .L3.81 (1.3.81 + Foramsulfuron (c31 )) Pyridat (c75) c62.c31.1.3.81 c31 .L3.81 (1.3.81 + Foramsulfuron (c31 )) Bentazon (c62)C75.C31.1.3.81 c31 .L3.81 (1.3.81 + foramsulfuron (c31)) pyridate (c75) c62.c31.1.3.81 c31.L3.81 (1.3.81 + foramsulfuron (c31)) bentazone ( c62)
C73.C31.1.3.81 c31 .L3.81 (1.3.81 + Foramsulfuron (c31 )) Metribuzin (c73) c1 16.c31 .L3.81 c31 .L3.81 (1.3.81 + Foramsulfuron (c31 )) Pendimethalin (c1 16) c61.c51 .L3.81 c51 .L3.81 (1.3.81 + Halosulfuron-m. (c51 )) Atrazin (c61 ) C73.C31.1.3.81 c31 .L3.81 (1.3.81 + foramsulfuron (c31)) metribuzin (c73) c1 16.c31.L3.81 c31.L3.81 (1.3.81 + foramsulfuron (c31)) pendimethalin (c1 16) c61.c51 .L3.81 c51 .L3.81 (1.3.81 + halosulfuron-m. (c51)) atrazine (c61)
C77.C51.1.3.81 c51 .L3.81 (1.3.81 + Halosulfuron-m. (c51 )) Terbuthylazin (c77) C77.C51.1.3.81 c51 .L3.81 (1.3.81 + halosulfuron-m. (C51)) terbuthylazine (c77)
C63.C51.1.3.81 c51 .L3.81 (1.3.81 + Halosulfuron-m. (c51 )) Bromoxynil (c63)C63.C51.1.3.81 c51 .L3.81 (1.3.81 + halosulfuron-m. (C51)) bromoxynil (c63)
C75.C51.1.3.81 c51 .L3.81 (1.3.81 + Halosulfuron-m. (c51 )) Pyridat (c75)C75.C51.1.3.81 c51 .L3.81 (1.3.81 + halosulfuron-m. (C51)) pyridate (c75)
C62.C51.1.3.81 c51 .L3.81 (1.3.81 + Halosulfuron-m. (c51 )) Bentazon (c62) C62.C51.1.3.81 c51 .L3.81 (1.3.81 + halosulfuron-m. (C51)) bentazone (c62)
C73.C51.1.3.81 c51 .L3.81 (1.3.81 + Halosulfuron-m. (c51 )) Metribuzin (c73) c1 16.c51 .L3.81 c51 .L3.81 (1.3.81 + Halosulfuron-m. (c51 )) Pendimethalin (c1 16) c61.c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron (c39)) Atrazin (c61 ) c77.c39.l.3.81 c39.L3.81 (1.3.81 + lodosulfuron (c39)) Terbuthylazin (c77) c63.c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron (c39)) Bromoxynil (c63) c75.c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron (c39)) Pyridat (c75) c62.c39.l.3.81 c39.L3.81 (1.3.81 + lodosulfuron (c39)) Bentazon (c62) c73.c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron (c39)) Metribuzin (c73) c1 16.c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron (c39)) Pendimethalin (c1 16) c61.c44.L3.81 c44.L3.81 (1.3.81 + Nicosulfuron (c44)) Atrazin (c61 ) c77.c44.L3.81 c44.L3.81 (1.3.81 + Nicosulfuron (c44)) Terbuthylazin (c77) c63.c44.L3.81 c44.L3.81 (1.3.81 + Nicosulfuron (c44)) Bromoxynil (c63) c75.c44.L3.81 c44.L3.81 (1.3.81 + Nicosulfuron (c44)) Pyridat (c75) c62.c44.L3.81 c44.L3.81 (1.3.81 + Nicosulfuron (c44)) Bentazon (c62) c73.c44.L3.81 c44.L3.81 (1.3.81 + Nicosulfuron (c44)) Metribuzin (c73) c1 16.c44.L3.81 c44.L3.81 (1.3.81 + Nicosulfuron (c44)) Pendimethalin (c1 16) c61.c52.L3.81 c52.L3.81 (1.3.81 + Primisulfuron-m. (c52)) Atrazin (c61 ) c77.c52.L3.81 c52.L3.81 (1.3.81 + Primisulfuron-m. (c52)) Terbuthylazin (c77) c63.c52.L3.81 c52.L3.81 (1.3.81 + Primisulfuron-m. (c52)) Bromoxynil (c63) c75.c52.L3.81 c52.L3.81 (1.3.81 + Primisulfuron-m. (c52)) Pyridat (c75) c62.c52.l.3.81 c52.L3.81 (1.3.81 + Primisulfuron-m. (c52)) Bentazon (c62) c73.c52.L3.81 c52.L3.81 (1.3.81 + Primisulfuron-m. (c52)) Metribuzin (c73) c1 16.c52.L3.81 c52.L3.81 (1.3.81 + Primisulfuron-m. (c52)) Pendimethalin (c1 16) c61.c53.L3.81 c53.L3.81 (1.3.81 + Rimsulfuron (c53)) Atrazin (c61 ) c77.c53.L3.81 c53.L3.81 (1.3.81 + Rimsulfuron (c53)) Terbuthylazin (c77) c63.c53.L3.81 c53.L3.81 (1.3.81 + Rimsulfuron (c53)) Bromoxynil (c63) c75.c53.L3.81 c53.L3.81 (1.3.81 + Rimsulfuron (c53)) Pyridat (c75) c62.c53.l.3.81 c53.L3.81 (1.3.81 + Rimsulfuron (c53)) Bentazon (c62) c73.c53.L3.81 c53.L3.81 (1.3.81 + Rimsulfuron (c53)) Metribuzin (c73) c1 16.c53.L3.81 c53.L3.81 (1.3.81 + Rimsulfuron (c53)) Pendimethalin (c1 16) c61 .c56.L3.81 c56.L3.81 (1.3.81 + Thifensulfuron (c56)) Atrazin (c61 ) c77.c56.L3.81 c56.L3.81 (1.3.81 + Thifensulfuron (c56)) Terbuthylazin (c77) c63.c56.L3.81 c56.L3.81 (1.3.81 + Thifensulfuron (c56)) Bromoxynil (c63) c75.c56.L3.81 c56.L3.81 (1.3.81 + Thifensulfuron (c56)) Pyridat (c75) c62.c56.L3.81 c56.L3.81 (1.3.81 + Thifensulfuron (c56)) Bentazon (c62) c73.c56.L3.81 c56.L3.81 (1.3.81 + Thifensulfuron (c56)) Metribuzin (c73) c1 16.c56.L3.81 c56.L3.81 (1.3.81 + Thifensulfuron (c56)) Pendimethalin (c1 16) c61.c58.L3.81 c58.L3.81 (1.3.81 + Triasulfuron (c58)) Atrazin (c61 ) c77.c58.L3.81 c58.L3.81 (1.3.81 + Triasulfuron (c58)) Terbuthylazin (c77) c63.c58.L3.81 c58.L3.81 (1.3.81 + Triasulfuron (c58)) Bromoxynil (c63) c75.c58.L3.81 c58.L3.81 (1.3.81 + Triasulfuron (c58)) Pyridat (c75) c62.c58.L3.81 c58.L3.81 (1.3.81 + Triasulfuron (c58)) Bentazon (c62) c73.c58.L3.81 c58.L3.81 (1.3.81 + Triasulfuron (c58)) Metribuzin (c73) c1 16.c58.L3.81 c58.L3.81 (1.3.81 + Triasulfuron (c58)) Pendimethalin (c1 16) c61.c59.L3.81 c59.L3.81 (1.3.81 + Tritosulfuron (c59)) Atrazin (c61 ) c77.c59.L3.81 c59.L3.81 (1.3.81 + Tritosulfuron (c59)) Terbuthylazin (c77) c63.c59.L3.81 c59.L3.81 (1.3.81 + Tritosulfuron (c59)) Bromoxynil (c63) c75.c59.L3.81 c59.L3.81 (1.3.81 + Tritosulfuron (c59)) Pyridat (c75) c62.c59.l.3.81 c59.L3.81 (1.3.81 + Tritosulfuron (c59)) Bentazon (c62) c73.c59.L3.81 c59.L3.81 (1.3.81 + Tritosulfuron (c59)) Metribuzin (c73) c1 16.c59.L3.81 c59.L3.81 (1.3.81 + Tritosulfuron (c59)) Pendimethalin (c1 16) c61.c43.L3.81 c43.L3.81 (1.3.81 + Metosulam (c43)) Atrazin (c61 ) c77.c43.L3.81 c43.L3.81 (1.3.81 + Metosulam (c43)) Terbuthylazin (c77) c63.c43.L3.81 c43.L3.81 (1.3.81 + Metosulam (c43)) Bromoxynil (c63) c75.c43.L3.81 c43.L3.81 (1.3.81 + Metosulam (c43)) Pyridat (c75) c62.c43.L3.81 c43.L3.81 (1.3.81 + Metosulam (c43)) Bentazon (c62) c73.c43.L3.81 c43.L3.81 (1.3.81 + Metosulam (c43)) Metribuzin (c73) c1 16.c43.L3.81 c43.L3.81 (1.3.81 + Metosulam (c43)) Pendimethalin (c1 16) c61.c29.L3.81 c29.L3.81 (1.3.81 + Flumetsulam (c29)) Atrazin (c61 ) c77.c29.l.3.81 c29.L3.81 (1.3.81 + Flumetsulam (c29)) Terbuthylazin (c77) c63.c29.L3.81 c29.L3.81 (1.3.81 + Flumetsulam (c29)) Bromoxynil (c63) c75.c29.L3.81 c29.L3.81 (1.3.81 + Flumetsulam (c29)) Pyridat (c75) c62.c29.l.3.81 c29.L3.81 (1.3.81 + Flumetsulam (c29)) Bentazon (c62) c73.c29.L3.81 c29.L3.81 (1.3.81 + Flumetsulam (c29)) Metribuzin (c73) c1 16.c29.L3.81 c29.L3.81 (1.3.81 + Flumetsulam (c29)) Pendimethalin (c1 16) c61.c27.L3.81 c27.L3.81 (1.3.81 + Florasulam (c27)) Atrazin (c61 ) c77.c27.l.3.81 c27.L3.81 (1.3.81 + Florasulam (c27)) Terbuthylazin (c77) c63.c27.L3.81 c27.L3.81 (1.3.81 + Florasulam (c27)) Bromoxynil (c63) c75.c27.L3.81 c27.L3.81 (1.3.81 + Florasulam (c27)) Pyridat (c75) c62.c27.l.3.81 c27.L3.81 (1.3.81 + Florasulam (c27)) Bentazon (c62) c73.c27.L3.81 c27.L3.81 (1.3.81 + Florasulam (c27)) Metribuzin (c73) c1 16.c27.L3.81 c27.L3.81 (1.3.81 + Florasulam (c27)) Pendimethalin (c1 16) c61 .c55.L3.81 c55.L3.81 (1.3.81 + Thiencarbazon (c55)) Atrazin (c61 ) c77.c55.L3.81 c55.L3.81 (1.3.81 + Thiencarbazon (c55)) Terbuthylazin (c77) c63.c55.L3.81 c55.L3.81 (1.3.81 + Thiencarbazon (c55)) Bromoxynil (c63) c75.c55.L3.81 c55.L3.81 (1.3.81 + Thiencarbazon (c55)) Pyridat (c75) c62.c55.L3.81 c55.L3.81 (1.3.81 + Thiencarbazon (c55)) Bentazon (c62) c73.c55.L3.81 c55.L3.81 (1.3.81 + Thiencarbazon (c55)) Metribuzin (c73) c1 16.c55.L3.81 c55.L3.81 (1.3.81 + Thiencarbazon (c55)) Pendimethalin (c1 16) c61.c33.L3.81 c33.L3.81 (1.3.81 + Imazamox (c33)) Atrazin (c61 ) c77.c33.l.3.81 c33.L3.81 (1.3.81 + Imazamox (c33)) Terbuthylazin (c77) c63.c33.L3.81 c33.L3.81 (1.3.81 + Imazamox (c33)) Bromoxynil (c63) c75.c33.L3.81 c33.L3.81 (1.3.81 + Imazamox (c33)) Pyridat (c75) c62.c33.l.3.81 c33.L3.81 (1.3.81 + Imazamox (c33)) Bentazon (c62) c73.c33.L3.81 c33.L3.81 (1.3.81 + Imazamox (c33)) Metribuzin (c73) c1 16.c33.L3.81 c33.L3.81 (1.3.81 + Imazamox (c33)) Pendimethalin (c1 16) c61.c35.L3.81 c35.L3.81 (1.3.81 + Imazapyr (c35)) Atrazin (c61 ) c77.c35.l.3.81 c35.L3.81 (1.3.81 + Imazapyr (c35)) Terbuthylazin (c77) c63.c35.L3.81 c35.L3.81 (1.3.81 + Imazapyr (c35)) Bromoxynil (c63) c75.c35.L3.81 c35.L3.81 (1.3.81 + Imazapyr (c35)) Pyridat (c75) c62.c35.l.3.81 c35.L3.81 (1.3.81 + Imazapyr (c35)) Bentazon (c62) c73.c35.L3.81 c35.L3.81 (1.3.81 + Imazapyr (c35)) Metribuzin (c73) c1 16.c35.L3.81 c35.L3.81 (1.3.81 + Imazapyr (c35)) Pendimethalin (c1 16) c61 .c37.L3.81 c37.L3.81 (1.3.81 + Imazethapyr (c37)) Atrazin (c61 ) c77.c37.L3.81 c37.L3.81 (1.3.81 + Imazethapyr (c37)) Terbuthylazin (c77) c63.c37.L3.81 c37.L3.81 (1.3.81 + Imazethapyr (c37)) Bromoxynil (c63) c75.c37.L3.81 c37.L3.81 (1.3.81 + Imazethapyr (c37)) Pyridat (c75) c62.c37.L3.81 c37.L3.81 (1.3.81 + Imazethapyr (c37)) Bentazon (c62) c73.c37.L3.81 c37.L3.81 (1.3.81 + Imazethapyr (c37)) Metribuzin (c73) c1 16.c37.L3.81 c37.L3.81 (1.3.81 + Imazethapyr (c37)) Pendimethalin (c1 16) c61 .c34.L3.81 c34.L3.81 (1.3.81 + Imazapic (c34)) Atrazin (c61 ) c77.c34.l.3.81 c34.L3.81 (1.3.81 + Imazapic (c34)) Terbuthylazin (c77) c63.c34.L3.81 c34.L3.81 (1.3.81 + Imazapic (c34)) Bromoxynil (c63) c75.c34.L3.81 c34.L3.81 (1.3.81 + Imazapic (c34)) Pyridat (c75) c62.c34.l.3.81 c34.L3.81 (1.3.81 + Imazapic (c34)) Bentazon (c62) c73.c34.L3.81 c34.L3.81 (1.3.81 + Imazapic (c34)) Metribuzin (c73) c1 16.c34.L3.81 c34.L3.81 (1.3.81 + Imazapic (c34)) Pendimethalin (c1 16) c61.c99.L3.81 c99.L3.81 (1.3.81 + Mesotrione (c99)) Atrazin (c61 ) c77.c99.l.3.81 c99.L3.81 (1.3.81 + Mesotrione (c99)) Terbuthylazin (c77) c63.c99.L3.81 c99.L3.81 (1.3.81 + Mesotrione (c99)) Bromoxynil (c63) c75.c99.L3.81 c99.L3.81 (1.3.81 + Mesotrione (c99)) Pyridat (c75) c62.c99.l.3.81 c99.L3.81 (1.3.81 + Mesotrione (c99)) Bentazon (c62) c73.c99.L3.81 c99.L3.81 (1.3.81 + Mesotrione (c99)) Metribuzin (c73) c1 16.c99.L3.81 c99.L3.81 (1.3.81 + Mesotrione (c99)) Pendimethalin (c1 16) c61.d 02.1.3.81 c102.L3.81 (1.3.81 + Sulcotrione (c102)) Atrazin (c61 ) c77.d 02.1.3.81 c102.L3.81 (1.3.81 + Sulcotrione (c102)) Terbuthylazin (c77) c63.c102.1.3.81 c102.L3.81 (1.3.81 + Sulcotrione (c102)) Bromoxynil (c63) c75.c102.1.3.81 c102.L3.81 (1.3.81 + Sulcotrione (c102)) Pyridat (c75) c62.c102.1.3.81 c102.L3.81 (1.3.81 + Sulcotrione (c102)) Bentazon (c62) c73.c102.1.3.81 c102.L3.81 (1.3.81 + Sulcotrione (c102)) Metribuzin (c73) c1 16.c102.L3.81 c102.L3.81 (1.3.81 + Sulcotrione (c102)) Pendimethalin (c1 16) c61.c104.1.3.81 c104.L3.81 (1.3.81 + Tembotrione (c104)) Atrazin (c61 ) c77.c104.1.3.81 c104.L3.81 (1.3.81 + Tembotrione (c104)) Terbuthylazin (c77) c63.c104.1.3.81 c104.L3.81 (1.3.81 + Tembotrione (c104)) Bromoxynil (c63) c75.c104.1.3.81 c104.L3.81 (1.3.81 + Tembotrione (c104)) Pyridat (c75) c62.c104.1.3.81 c104.L3.81 (1.3.81 + Tembotrione (c104)) Bentazon (c62) c73.c104.1.3.81 c104.L3.81 (1.3.81 + Tembotrione (c104)) Metribuzin (c73) c1 16.c104.L3.81 c104.L3.81 (1.3.81 + Tembotrione (c104)) Pendimethalin (c1 16) c61 .c98.L3.81 c98.L3.81 (1.3.81 + Isoxaflutole (c98)) Atrazin (c61 ) c77.c98.L3.81 c98.L3.81 (1.3.81 + Isoxaflutole (c98)) Terbuthylazin (c77) c63.c98.L3.81 c98.L3.81 (1.3.81 + Isoxaflutole (c98)) Bromoxynil (c63) c75.c98.L3.81 c98.L3.81 (1.3.81 + Isoxaflutole (c98)) Pyridat (c75) c62.c98.l.3.81 c98.L3.81 (1.3.81 + Isoxaflutole (c98)) Bentazon (c62) c73.c98.L3.81 c98.L3.81 (1.3.81 + Isoxaflutole (c98)) Metribuzin (c73) c1 16.c98.L3.81 c98.L3.81 (1.3.81 + Isoxaflutole (c98)) Pendimethalin (c1 16) c61.c105.1.3.81 c105.L3.81 (1.3.81 + Topramezone (c105)) Atrazin (c61 ) c77.c105.L3.81 c105.L3.81 (1.3.81 + Topramezone (c105)) Terbuthylazin (c77) c63.c105.1.3.81 c105.L3.81 (1.3.81 + Topramezone (c105)) Bromoxynil (c63) c75.c105.L3.81 c105.L3.81 (1.3.81 + Topramezone (c105)) Pyridat (c75) c62.c105.1.3.81 c105.L3.81 (1.3.81 + Topramezone (c105)) Bentazon (c62) c73.c105.L3.81 c105.L3.81 (1.3.81 + Topramezone (c105)) Metribuzin (c73) c1 16.c105.L3.81 c105.L3.81 (1.3.81 + Topramezone (c105)) Pendimethalin (c1 16) c61.c106.1.3.81 c106.L3.81 (1.3.81 + Bicyclopyrone (c106)) Atrazin (c61 ) c77.c106.L3.81 c106.L3.81 (1.3.81 + Bicyclopyrone (c106)) Terbuthylazin (c77) c63.c106.1.3.81 c106.L3.81 (1.3.81 + Bicyclopyrone (c106)) Bromoxynil (c63) c75.c106.L3.81 c106.L3.81 (1.3.81 + Bicyclopyrone (c106)) Pyridat (c75) c62.c106.1.3.81 c106.L3.81 (1.3.81 + Bicyclopyrone (c106)) Bentazon (c62) c73.c106.L3.81 c106.L3.81 (1.3.81 + Bicyclopyrone (c106)) Metribuzin (c73) c1 16.c106.L3.81 c106.L3.81 (1.3.81 + Bicyclopyrone (c106)) Pendimethalin (c1 16) c61.c132.L3.81 c132.L3.81 (1.3.81 + Pyroxasulfone (c132)) Atrazin (c61 ) c77.c132.1.3.81 c132.L3.81 (1.3.81 + Pyroxasulfone (c132)) Terbuthylazin (c77) c63.c132.1.3.81 c132.L3.81 (1.3.81 + Pyroxasulfone (c132)) Bromoxynil (c63) c75.c132.1.3.81 c132.L3.81 (1.3.81 + Pyroxasulfone (c132)) Pyridat (c75) c62.c132.1.3.81 c132.L3.81 (1.3.81 + Pyroxasulfone (c132)) Bentazon (c62) c73.c132.1.3.81 c132.L3.81 (1.3.81 + Pyroxasulfone (c132)) Metribuzin (c73) c1 16.c132.L3.81 c132.L3.81 (1.3.81 + Pyroxasulfone (c132)) Pendimethalin (c1 16) c61 .c1 18.L3.81 d 18.1.3.81 (1.3.81 + Acetochlor (d 18)) Atrazin (c61 ) c77.c1 18.1.3.81 d 18.1.3.81 (1.3.81 + Acetochlor (d 18)) Terbuthylazin (c77) c63.c1 18.L3.81 d 18.1.3.81 (1.3.81 + Acetochlor (d 18)) Bromoxynil (c63) c75.c1 18.1.3.81 d 18.1.3.81 (1.3.81 + Acetochlor (d 18)) Pyridat (c75) c62.c1 18.1.3.81 d 18.1.3.81 (1.3.81 + Acetochlor (d 18)) Bentazon (c62) c73.c1 18.1.3.81 d 18.1.3.81 (1.3.81 + Acetochlor (d 18)) Metribuzin (c73) c1 16.c1 18.L3.81 d 18.1.3.81 (1.3.81 + Acetochlor (d 18)) Pendimethalin (c1 16) c61.c121 .L3.81 c121 .L3.81 (1.3.81 + Dimethenamid-P Atrazin (c61 ) (C121 ))C73.C51.1.3.81 c51 .L3.81 (1.3.81 + halosulfuron-m. (C51)) metribuzin (c73) c1 16.c51 .L3.81 c51 .L3.81 (1.3.81 + halosulfuron-m (c51)) pendimethalin (c1 16) c61.c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron (c39)) atrazine (c61) c77.c39.l.3.81 c39.L3.81 (1.3.81 + lodosulfuron (c39)) terbuthylazine (c77) c63.c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron (c39)) bromoxynil ( c63) c75.c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron (c39)) pyridate (c75) c62.c39.l.3.81 c39.L3.81 (1.3.81 + lodosulfuron (c39)) Bentazone (c62) c73.c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron (c39)) metribuzin (c73) c1 16.c39.L3.81 c39.L3.81 (1.3.81 + lodosulfuron ( c39)) pendimethalin (c1 16) c61.c44.L3.81 c44.L3.81 (1.3.81 + nicosulfuron (c44)) atrazine (c61) c77.c44.L3.81 c44.L3.81 (1.3.81 + Nicosulfuron (c44)) terbuthylazine (c77) c63.c44.L3.81 c44.L3.81 (1.3.81 + nicosulfuron (c44)) bromoxynil (c63) c75.c44.L3.81 c44.L3.81 (1.3 .81 + nicosulfuron (c44)) pyridate (c75) c62.c44.L3.81 c44.L3.81 (1.3.81 + nicosulfuron (c44)) bentazone (c62) c73.c44.L3.81 c44.L3.81 (1.3.81 + nicosulfuron (c44)) metribuzin (c73) c1 16.c44.L3.81 c44.L3.81 (1.3.81 + nicosulfuron (c44)) pendimethalin (c1 16) c61.c52.L3.81 c52 .L3.81 (1.3.81 + primisulfuron-m. (C52)) atrazine ( c61) c77.c52.L3.81 c52.L3.81 (1.3.81 + primisulfuron-m. (c52)) terbuthylazine (c77) c63.c52.L3.81 c52.L3.81 (1.3.81 + primisulfuron-m. (c52)) bromoxynil (c63) c75.c52.L3.81 c52.L3.81 ( 1.3.81 + primisulfuron-m. (C52)) pyridate (c75) c62.c52.l.3.81 c52.L3.81 (1.3.81 + primisulfuron-m. (C52)) bentazone (c62) c73.c52.L3 .81 c52.L3.81 (1.3.81 + primisulfuron-m. (C52)) metribuzin (c73) c1 16.c52.L3.81 c52.L3.81 (1.3.81 + primisulfuron-m. (C52)) Pendimethalin (c1 16) c61.c53.L3.81 c53.L3.81 (1.3.81 + rimsulfuron (c53)) atrazine (c61) c77.c53.L3.81 c53.L3.81 (1.3.81 + rimsulfuron ( c53)) terbuthylazine (c77) c63.c53.L3.81 c53.L3.81 (1.3.81 + rimsulfuron (c53)) bromoxynil (c63) c75.c53.L3.81 c53.L3.81 (1.3.81 + Rimsulfuron (c53)) pyridate (c75) c62.c53.l.3.81 c53.L3.81 (1.3.81 + rimsulfuron (c53)) bentazone (c62) c73.c53.L3.81 c53.L3.81 (1.3. 81 + rimsulfuron (c53)) metribuzin (c73) c1 16.c53.L3.81 c53.L3.81 (1.3.81 + rimsulfuron (c53)) pendimethalin (c1 16) c61 .c56.L3.81 c56.L3. 81 (1.3.81 + thifensulfuron (c56)) atrazine (c61) c77.c56.L3.81 c56.L3.81 (1.3. 81 + thifensulfuron (c56)) terbuthylazine (c77) c63.c56.L3.81 c56.L3.81 (1.3.81 + thifensulfuron (c56)) bromoxynil (c63) c75.c56.L3.81 c56.L3.81 ( 1.3.81 + thifensulfuron (c56)) pyridate (c75) c62.c56.L3.81 c56.L3.81 (1.3.81 + thifensulfuron (c56)) bentazone (c62) c73.c56.L3.81 c56.L3. 81 (1.3.81 + thifensulfuron (c56)) metribuzin (c73) c1 16.c56.L3.81 c56.L3.81 (1.3.81 + thifensulfuron (c56)) pendimethalin (c1 16) c61.c58.L3.81 c58.L3.81 (1.3.81 + triasulfuron (c58)) atrazine (c61) c77.c58.L3.81 c58.L3.81 (1.3.81 + triasulfuron (c58)) terbuthylazine (c77) c63.c58.L3 .81 c58.L3.81 (1.3.81 + triasulfuron (c58)) bromoxynil (c63) c75.c58.L3.81 c58.L3.81 (1.3.81 + triasulfuron (c58)) pyridate (c75) c62.c58 .L3.81 c58.L3.81 (1.3.81 + triasulfuron (c58)) bentazone (c62) c73.c58.L3.81 c58.L3.81 (1.3.81 + triasulfuron (c58)) metribuzin (c73) c1 16.c58.L3.81 c58.L3.81 (1.3.81 + triasulfuron (c58)) pendimethalin (c1 16) c61.c59.L3.81 c59.L3.81 (1.3.81 + tritosulfuron (c59)) Atrazine (c61) c77.c59.L3.81 c59.L3.81 (1.3.81 + tritosulfuron (c59)) terbuthylazine (c77) c63.c59.L3.81 c59.L3.81 (1.3.81 + tritosulfuron (c59 )) Bromoxynil (c63) c75.c59.L3.81 c59.L3.81 (1.3.81 + tritosulfuron (c59)) pyridate (c75) c62.c59.l.3.81 c59.L3.81 (1.3.81 + tritosulfuron (c59)) Bentazone (c62) c73.c59.L3.81 c59.L3.81 (1.3.81 + tritosulfuron (c59)) metribuzin (c73) c1 16.c59.L3.81 c59.L3.81 (1.3. 81 + tritosulfuron (c59)) pendimethalin (c1 16) c61.c43.L3.81 c43.L3.81 (1.3.81 + metosulam (c43)) atrazine (c61) c77.c43.L3.81 c43.L3.81 (1.3.81 + metosulam (c43)) terbuthylazine (c77) c63.c43.L3.81 c43.L3.81 (1.3.81 + metosulam (c43)) bromoxynil (c63) c75.c43.L3.81 c43.L3 .81 (1.3.81 + metosulam (c43)) pyridate (c75) c62.c43.L3.81 c43.L3.81 (1.3.81 + metosulam (c43)) bentazone (c62) c73.c43.L3.81 c43 .L3.81 (1.3.81 + metosulam (c43)) metribuzin (c73) c1 16.c43. L3.81 c43.L3.81 (1.3.81 + metosulam (c43)) pendimethalin (c1 16) c61.c29.L3.81 c29.L3.81 (1.3.81 + flumetsulam (c29)) atrazine (c61) c77 .c29.l.3.81 c29.L3.81 (1.3.81 + flumetsulam (c29)) terbuthylazine (c77) c63.c29.L3.81 c29.L3.81 (1.3.81 + flumetsulam (c29)) bromoxynil (c63 ) c75.c29.L3.81 c29.L3.81 (1.3.81 + flumetsulam (c29)) pyridate (c75) c62.c29.l.3.81 c29.L3.81 (1.3.81 + flumetsulam (c29)) Bentazone (c62) c73.c29.L3.81 c29.L3.81 (1.3.81 + flumetsulam (c29)) metribuzin (c73) c1 16.c29.L3.81 c29.L3.81 (1.3.81 + flumetsulam (c29 )) Pendimethalin (c1 16) c61.c27.L3.81 c27.L3.81 (1.3.81 + florasulam (c27)) atrazine (c61) c77.c27.l.3.81 c27.L3.81 (1.3.81 + Florasulam (c27)) terbuthylazine (c77) c63.c27.L3.81 c27.L3.81 (1.3.81 + florasulam (c27)) bromoxynil (c63) c75.c27.L3.81 c27.L3.81 (1.3. 81 + florasulam (c27)) pyridate (c75) c62.c27.l.3.81 c27.L3.81 (1.3.81 + florasulam (c27)) bentazone (c62) c73.c27.L3.81 c27.L3.81 ( 1.3.81 + florasulam (c27)) metribuzin (c73) c1 16.c27.L3.81 c27.L3.81 (1 .3.81 + florasulam (c27)) pendimethalin (c1 16) c61 .c55.L3.81 c55.L3.81 (1.3.81 + thiencarbazone (c55)) atrazine (c61) c77.c55.L3.81 c55.L3. 81 (1.3.81 + thiencarbazone (c55)) terbuthylazine (c77) c63.c55.L3.81 c55.L3.81 (1.3.81 + thiencarbazone (c55)) bromoxynil (c63) c75.c55.L3.81 c55. L3.81 (1.3.81 + thiencarbazone (c55)) pyridate (c75) c62.c55.L3.81 c55.L3.81 (1.3.81 + thiencarbazone (c55)) bentazone (c62) c73.c55.L3.81 c55.L3.81 (1.3.81 + thiencarbazone (c55)) metribuzin (c73) c1 16.c55.L3.81 c55.L3.81 (1.3.81 + thiencarbazone (c55)) pendimethalin (c1 16) c61.c33 .L3.81 c33.L3.81 (1.3.81 + imazamox (c33)) atrazine (c61) c77.c33.l.3.81 c33.L3.81 (1.3.81 + imazamox (c33)) terbuthylazine (c77) c63 .c33.L3.81 c33.L3.81 (1.3.81 + imazamox (c33)) bromoxynil (c63) c75.c33.L3.81 c33.L3.81 (1.3.81 + imazamox (c33)) pyridate (c75 ) c62.c33.l.3.81 c33.L3.81 (1.3.81 + imazamox (c33)) bentazone (c62) c73.c33.L3.81 c33.L3.81 (1.3.81 + imazamox (c33)) metribuzin ( c73) c1 16.c33.L3.81 c33.L3.81 (1.3.81 + imazamox (c33)) pendimethalin (c1 16) c61.c35.L3.81 c35.L3.81 (1.3.81 + imazapyr (c35 ) Atrazine (c61) c77.c35.l.3.81 c35.L3.81 (1.3.81 + imazapyr (c35)) terbuthylazine (c77) c63.c35.L3.81 c35.L3.81 (1.3.81 + imazapyr (c35)) Bromoxynil (c63) c75.c35.L3.81 c35.L3.81 (1.3.81 + imazapyr (c35)) pyridate (c75) c62.c35.l.3.81 c35.L3.81 (1.3.81 + Imazapyr (c35)) bentazone (c62) c73.c35.L3.81 c35.L3.81 (1.3.81 + imazapyr (c35)) metribuzin (c73) c1 16.c35.L3.81 c35.L3.81 ( 1.3.81 + imazapyr (c35)) pendimethalin (c1 16) c61 .c37.L3.81 c37.L3.81 (1.3.81 + imazethapyr (c37)) atrazine (c61) c77.c37.L3.81 c37.L3 .81 (1.3.81 + imazethapyr (c37)) terbuthylazine (c77) c63.c37.L3.81 c37.L3.81 (1.3.81 + imazethapyr (c37)) bromoxynil (c63) c75.c37.L3.81 c37 .L3.81 (1.3.81 + imazethapyr (c37)) pyridate (c75) c62.c37.L3.81 c37.L3.81 (1.3.81 + Imazet hapyr (c37)) Bentazone (c62) c73.c37.L3.81 c37.L3.81 (1.3.81 + imazethapyr (c37)) metribuzin (c73) c1 16.c37.L3.81 c37.L3.81 (1.3 .81 + imazethapyr (c37)) pendimethalin (c1 16) c61 .c34.L3.81 c34.L3.81 (1.3.81 + imazapic (c34)) atrazine (c61) c77.c34.l.3.81 c34.L3. 81 (1.3.81 + imazapic (c34)) terbuthylazine (c77) c63.c34.L3.81 c34.L3.81 (1.3.81 + imazapic (c34)) bromoxynil (c63) c75.c34.L3.81 c34. L3.81 (1.3.81 + imazapic (c34)) pyridate (c75) c62.c34.l.3.81 c34.L3.81 (1.3.81 + imazapic (c34)) bentazone (c62) c73.c34.L3.81 c34.L3.81 (1.3.81 + imazapic (c34)) metribuzin (c73) c1 16.c34.L3.81 c34.L3.81 (1.3.81 + imazapic (c34)) pendimethalin (c1 16) c61.c99 .L3.81 c99.L3.81 (1.3.81 + mesotrione (c99)) atrazine (c61) c77.c99.l.3.81 c99.L3.81 (1.3.81 + mesotrione (c99)) terbuthylazine (c77) c63 .c99.L3.81 c99.L3.81 (1.3.81 + mesotrione (c99)) bromoxynil (c63) c75.c99.L3.81 c99.L3.81 (1.3.81 + mesotrione (c99)) pyridate (c75 ) c62.c99.l.3.81 c99.L3.81 (1.3.81 + mesotrione (c99)) bentazone (c62) c73.c99 .L3.81 c99.L3.81 (1.3.81 + mesotrione (c99)) metribuzin (c73) c1 16.c99.L3.81 c99.L3.81 (1.3.81 + mesotrione (c99)) pendimethalin (c1 16 ) c61.d 02.1.3.81 c102.L3.81 (1.3.81 + sulcotrione (c102)) atrazine (c61) c77.d 02.1.3.81 c102.L3.81 (1.3.81 + sulcotrione (c102)) terbuthylazine (c77 ) c63.c102.1.3.81 c102.L3.81 (1.3.81 + sulcotrione (c102)) bromoxynil (c63) c75.c102.1.3.81 c102.L3.81 (1.3.81 + sulcotrione (c102)) pyridate (c75) c62.c102.1.3.81 c102.L3.81 (1.3.81 + sulcotrione (c102)) bentazone (c62) c73.c102.1.3.81 c102.L3.81 (1.3.81 + sulcotrione (c102) ) Metribuzin (c73) c1 16.c102.L3.81 c102.L3.81 (1.3.81 + sulcotrione (c102)) pendimethalin (c1 16) c61.c104.1.3.81 c104.L3.81 (1.3.81 + Tembotrione (c104)) atrazine (c61) c77.c104.1.3.81 c104.L3.81 (1.3.81 + tembotrione (c104)) terbuthylazine (c77) c63.c104.1.3.81 c104.L3.81 (1.3.81 + tembotrione (c104)) bromoxynil (c63) c75.c104.1.3.81 c104.L3.81 (1.3.81 + tembotrione (c104)) pyridate ( c75) c62.c104.1.3.81 c104.L3.81 (1.3.81 + tembotrione (c104)) bentazone (c62) c73.c104.1.3.81 c104.L3.81 (1.3.81 + tembotrione (c104)) Metribuzin (c73) c1 16.c104.L3.81 c104.L3.81 (1.3.81 + tembotrione (c104)) pendimethalin (c1 16) c61 .c98.L3.81 c98.L3.81 (1.3.81 + isoxaflutole (c98)) atrazine (c61) c77.c98.L3.81 c98.L3.81 (1.3.81 + isoxaflutole (c98)) terbuthylazine (c77) c63.c98.L3.81 c98.L3.81 (1.3.81 + Isoxaflutole (c98)) bromoxynil (c63) c75.c98.L3.81 c98.L3.81 (1.3.81 + isoxaflutole (c98)) pyridate (c75) c62.c98.l.3.81 c98.L3.81 (1.3 .81 + isoxaflutole (c98)) bentazone (c62) c73.c98.L3.81 c98.L3.81 (1.3.81 + isoxaflutole (c98)) metribuzin (c73) c1 16.c98.L3.81 c98.L3. 81 (1.3.81 + isoxaflutole (c98)) pendimethalin (c1 16) c61.c105.1.3.81 c105.L3.81 (1.3.81 + toprame zone (c105)) atrazine (c61) c77.c105.L3.81 c105 .L3.81 (1.3.81 + toprame zone (c105)) Terbuthylazine (c77) c63.c105.1.3.81 c105.L3.81 (1.3.81 + Toprame zone (c105)) Bromoxynil (c63) c75.c105.L3.81 c105.L3.81 (1.3.81 + Toprame zone (c105 )) Pyridate (c75) c62.c105.1.3.81 c105.L3.81 (1.3.81 + toprame zone (c105)) bentazone (c62) c73.c105.L3.81 c105.L3.81 (1.3.81 + toprame zone (c105)) metribuzin (c73) c1 16.c105.L3.81 c105.L3.81 (1.3.81 + topram zone (c105)) pendimethalin (c1 16) c61.c106.1.3.81 c106.L3.81 (1.3 .81 + bicyclopyrone (c106)) atrazine (c61) c77.c106.L3.81 c106.L3.81 (1.3.81 + bicyclopyrone (c106)) terbuthylazine (c77) c63.c106.1.3.81 c106.L3.81 (1.3.81 + Bicyclopyrone (c106)) Bromoxynil (c63) c75.c106.L3.81 c106.L3.81 (1.3.81 + bicyclopyrone (c106)) pyridate (c75) c62.c106.1.3.81 c106.L3 .81 (1.3.81 + bicyclopyrone (c106)) bentazone (c62) c73.c106.L3.81 c106.L3.81 (1.3.81 + bicyclopyrone (c106)) metribuzin (c73) c1 16.c106.L3.81 c106.L3.81 (1.3.81 + bicyclopyrone (c106)) pendimethalin (c1 16) c61.c132.L3.81 c132.L3.81 (1.3.81 + pyroxasulfone (c132)) atrazine (c61) c77.c1 32.1.3.81 c132.L3.81 (1.3.81 + pyroxasulfones (c132)) terbuthylazine (c77) c63.c132.1.3.81 c132.L3.81 (1.3.81 + pyroxasulfones (c132)) bromoxynil (c63) c75. c132.1.3.81 c132.L3.81 (1.3.81 + pyroxasulfones (c132)) pyridate (c75) c62.c132.1.3.81 c132.L3.81 (1.3.81 + pyroxasulfones (c132)) bentazone (c62) c73.c132.1.3.81 c132.L3.81 (1.3.81 + pyroxasulfones (c132)) metribuzin (c73) c1 16.c132.L3.81 c132.L3.81 (1.3.81 + pyroxasulfones (c132)) pendimethalin (c1 16) c61 .c1 18.L3.81 d 18.1.3.81 (1.3.81 + acetochlor (d 18)) atrazine (c61) c77.c1 18.1.3.81 d 18.1.3.81 (1.3.81 + acetochlor (d )) Terbuthylazine (c77) c63.c1 18.L3.81 d 18.1.3.81 (1.3.81 + acetochlor (d 18)) Bromoxynil (c63) c75.c1 18.1.3.81 d 18.1.3.81 (1.3.81 + acetochloro) d 18)) pyridate (c75) c62.c1 18.1.3.81 d 18.1.3.81 (1.3.81 + acetochlor (d 18)) bentazone (c62) c73.c1 18.1.3.81 d 18.1.3.81 (1.3.81 + acetochloro) d 18)) metribuzin (c73) c1 16.c1 18.L3.81 d 18.1.3.81 (1.3.81 + acetochlor (d 18)) pendimethalin (c1 16) c61.c121 .L3.81 c121 .L3.81 (1.3.81 + dimethenamid-P atrazine (c61) (C121))
c77.c121 .1.3.81 c121 .L3.81 (1.3.81 + Dimethenamid-P Terbuthylazin (c77)c77.c121 .1.3.81 c121 .L3.81 (1.3.81 + dimethenamid-P terbuthylazine (c77)
(C121 )) (C121))
c63.c121 .L3.81 c121 .L3.81 (1.3.81 + Dimethenamid-P Bromoxynil (c63)c63.c121 .L3.81 c121 .L3.81 (1.3.81 + dimethenamid-P bromoxynil (c63)
(C121 )) (C121))
C75.C121 .1.3.81 c121 .L3.81 (1.3.81 + Dimethenamid-P Pyridat (c75) C75.C121 .1.3.81 c121 .L3.81 (1.3.81 + dimethenamid-P pyridate (c75)
(C121 )) (C121))
c62.c121 .1.3.81 c121 .L3.81 (1.3.81 + Dimethenamid-P Bentazon (c62)c62.c121 .1.3.81 c121 .L3.81 (1.3.81 + dimethenamid-P bentazone (c62)
(C121 )) (C121))
C73.C121 .1.3.81 c121 .L3.81 (1.3.81 + Dimethenamid-P Metribuzin (c73) C73.C121 .1.3.81 c121 .L3.81 (1.3.81 + dimethenamid-P metribuzin (c73)
(C121 )) (C121))
c1 16.c121 .L3.81 c121 .L3.81 (1.3.81 + Dimethenamid-P Pendimethalin (c1 16)c1 16.c121 .L3.81 c121 .L3.81 (1.3.81 + dimethenamid-P pendimethalin (c1 16)
(C121 )) (C121))
c61 .c127.L3.81 c127.L3.81 (1.3.81 + S-Metolachlor (c127)) Atrazin (c61 ) c77.c127.l.3.81 c127.L3.81 (1.3.81 + S-Metolachlor (d 27)) Terbuthylazin (c77) c63.c127.L3.81 c127.L3.81 (1.3.81 + S-Metolachlor (d 27)) Bromoxynil (c63) c75.c127.L3.81 c127.L3.81 (1.3.81 + S-Metolachlor (d 27)) Pyridat (c75) c62.c127.l.3.81 c127.L3.81 (1.3.81 + S-Metolachlor (d 27)) Bentazon (c62) c73.c127.L3.81 c127.L3.81 (1.3.81 + S-Metolachlor (d 27)) Metribuzin (c73) c1 16.c127.L3.81 c127.L3.81 (1.3.81 + S-Metolachlor (d 27)) Pendimethalin (c1 16) c61.c128.L3.81 c128.L3.81 (1.3.81 + Pethoxamid (c128)) Atrazin (c61 ) c77.c128.L3.81 c128.L3.81 (1.3.81 + Pethoxamid (c128)) Terbuthylazin (c77) c63.c128.L3.81 c128.L3.81 (1.3.81 + Pethoxamid (c128)) Bromoxynil (c63) c75.c128.L3.81 c128.L3.81 (1.3.81 + Pethoxamid (c128)) Pyridat (c75) c62.c128.L3.81 c128.L3.81 (1.3.81 + Pethoxamid (c128)) Bentazon (c62) c73.c128.L3.81 c128.L3.81 (1.3.81 + Pethoxamid (c128)) Metribuzin (c73) c1 16.c128.L3.81 c128.L3.81 (1.3.81 + Pethoxamid (c128)) Pendimethalin (c1 16) c61.c123.L3.81 c123.L3.81 (1.3.81 + Flufenacet (c123)) Atrazin (c61 ) c77.c123.1.3.81 c123.L3.81 (1.3.81 + Flufenacet (d 23)) Terbuthylazin (c77) c63.c123.L3.81 c123.L3.81 (1.3.81 + Flufenacet (d 23)) Bromoxynil (c63) c75.c123.L3.81 c123.L3.81 (1.3.81 + Flufenacet (d 23)) Pyridat (c75) c62.c123.L3.81 c123.L3.81 (1.3.81 + Flufenacet (d 23)) Bentazon (c62) c73.c123.L3.81 c123.L3.81 (1.3.81 + Flufenacet (d 23)) Metribuzin (c73) c1 16.c123.L3.81 c123.L3.81 (1.3.81 + Flufenacet (d 23)) Pendimethalin (c1 16) c61 .c1 10.L3.81 d 10.1.3.81 (1.3.81 + Glyphosate-i. (c1 10)) Atrazin (c61 ) c77.c1 10.1.3.81 d 10.1.3.81 (1.3.81 + Glyphosate-i. (c1 10)) Terbuthylazin (c77) c63.c1 10.L3.81 d 10.1.3.81 (1.3.81 + Glyphosate-i. (c1 10)) Bromoxynil (c63) c75.c1 10.1.3.81 d 10.1.3.81 (1.3.81 + Glyphosate-i. (c1 10)) Pyridat (c75) c62.c1 10.1.3.81 d 10.1.3.81 (1.3.81 + Glyphosate-i. (c1 10)) Bentazon (c62) c73.c1 10.1.3.81 d 10.1.3.81 (1.3.81 + Glyphosate-i. (c1 10)) Metribuzin (c73) c116.c110.L3.81 d 10.1.3.81 (1.3.81 + Glyphosate-i. (c110)) Pendimethalin (c116) c61.c111.L3.81 d 11.1.3.81 (1.3.81 + Glyphosate-t. (c111)) Atrazin (c61) c77.c111.L3.81 d 11.1.3.81 (1.3.81 + Glyphosate-t. (c111)) Terbuthylazin (c77) c63.c111.L3.81 d 11.1.3.81 (1.3.81 + Glyphosate-t. (c111)) Bromoxynil (c63) c75.c111.L3.81 d 11.1.3.81 (1.3.81 + Glyphosate-t. (c111)) Pyridat (c75) c62.c111.l.3.81 d 11.1.3.81 (1.3.81 + Glyphosate-t. (c111)) Bentazon (c62) c73.c111.L3.81 d 11.1.3.81 (1.3.81 + Glyphosate-t. (c111)) Metribuzin (c73) c116.c111.L3.81 d 11.1.3.81 (1.3.81 + Glyphosate-t. (c111)) Pendimethalin (c116) c61.c115.L3.81 c115.L3.81 (1.3.81 + Glufosinate-a. (d 15)) Atrazin (c61) c77.c115.1.3.81 c115.L3.81 (1.3.81 + Glufosinate-a. (d 15)) Terbuthylazin (c77) c63.c115.L3.81 c115.L3.81 (1.3.81 + Glufosinate-a. (d 15)) Bromoxynil (c63) c75.c115.1.3.81 c115.L3.81 (1.3.81 + Glufosinate-a. (d 15)) Pyridat (c75) c62.c115.1.3.81 c115.L3.81 (1.3.81 + Glufosinate-a. (d 15)) Bentazon (c62) c73.c115.1.3.81 c115.L3.81 (1.3.81 + Glufosinate-a. (d 15)) Metribuzin (c73) c116.c115.L3.81 c115.L3.81 (1.3.81 + Glufosinate-a. (d 15)) Pendimethalin (c116) c61.c112.L3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c112)) Atrazin (c61) c77.c112.1.3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c112)) Terbuthylazin (c77) c63.c112.L3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c112)) Bromoxynil (c63) c75.c112.1.3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c112)) Pyridat (c75) c62.c112.1.3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c112)) Bentazon (c62) c73.c112.1.3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c112)) Metribuzin (c73) c116.c112.L3.81 d 12.1.3.81 (1.3.81 + Bialaphos (c112)) Pendimethalin (c116) c61.c133.L3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) Atrazin (c61) c77.c133.1.3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) Terbuthylazin (c77) c142.c133.1.3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) Diflufenzopyr (c142) c116.c133.L3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) Pendimethalin (c116) c61.c138.L3.81 c138.L3.81 (1.3.81 + MCPA (c138)) Atrazin (c61) c77.c138.L3.81 c138.L3.81 (1.3.81 + MCPA (c138)) Terbuthylazin (c77) c142.c138.1.3.81 c138.L3.81 (1.3.81 + MCPA (c138)) Diflufenzopyr (c142) c116.c138.L3.81 c138.L3.81 (1.3.81 + MCPA(c138)) Pendimethalin (c116) c61.c136.L3.81 c136.L3.81 (1.3.81 + Dicamba (c136)) Atrazin (c61) c77.c136.L3.81 c136.L3.81 (1.3.81 + Dicamba (c136)) Terbuthylazin (c77) c142.c136.1.3.81 c136.L3.81 (1.3.81 + Dicamba (c136)) Diflufenzopyr (c142) c116.c136.L3.81 c136.L3.81 (1.3.81 + Dicamba (c136)) Pendimethalin (c116) c61.c135.L3.81 d 35.1.3.81 (1.3.81 + Clopyralid (c135)) Atrazin (c61) c77.c135.L3.81 d 35.1.3.81 (1.3.81 + Clopyralid (c135)) Terbuthylazin (c77) c142.c135.1.3.81 d 35.1.3.81 (1.3.81 + Clopyralid (c135)) Diflufenzopyr (c142) c116.c135.L3.81 d 35.1.3.81 (1.3.81 + Clopyralid (c135)) Pendimethalin (c116) c61.c137.1.3.81 c137.L3.81 (1.3.81 + Fluroxypyr (c137)) Atrazin (c61) c77.c137.1.3.81 c137.L3.81 (1.3.81 + Fluroxypyr (d 37)) Terbuthylazin (c77) c142.c137.1.3.81 c137.L3.81 (1.3.81 + Fluroxypyr (c137)) Diflufenzopyr (c142) c1 16.c137.L3.81 c137.L3.81 (1.3.81 + Fluroxypyr (d 37)) Pendimethalin (c1 16) c61 .c141 .L3.81 c141 .1.3.81 (1.3.81 + Aminocyclopyrachlor Atrazin (c61 )c61 .c127.L3.81 c127.L3.81 (1.3.81 + S-metolachlor (c127)) atrazine (c61) c77.c127.l.3.81 c127.L3.81 (1.3.81 + S-metolachlor (d 27)) Terbuthylazine (c77) c63.c127.L3.81 c127.L3.81 (1.3.81 + S-metolachlor (d27)) Bromoxynil (c63) c75.c127.L3.81 c127.L3.81 (1.3 .81 + S-metolachlor (d27)) pyridate (c75) c62.c127.l.3.81 c127.L3.81 (1.3.81 + S-metolachlor (d27)) bentazone (c62) c73.c127.L3. 81 c127.L3.81 (1.3.81 + S-metolachlor (d27)) metribuzin (c73) c1 16.c127.L3.81 c127.L3.81 (1.3.81 + S-metolachlor (d27)) pendimethalin (c1 16) c61.c128.L3.81 c128.L3.81 (1.3.81 + pethoxamide (c128)) atrazine (c61) c77.c128.L3.81 c128.L3.81 (1.3.81 + pethoxamide (c128 )) Terbuthylazine (c77) c63.c128.L3.81 c128.L3.81 (1.3.81 + pethoxamide (c128)) Bromoxynil (c63) c75.c128.L3.81 c128.L3.81 (1.3.81 + pethoxamide (c128)) pyridate (c75) c62.c128.L3.81 c128.L3.81 (1.3.81 + pethoxamide (c128)) bentazone (c62) c73.c128.L3.81 c128.L3.81 (1.3.81 + Pethoxamide (c128)) metribuzin (c73) c1 16.c128.L3.81 c128.L3.81 (1.3.81 + Pet hoxamide (c128)) pendimethalin (c1 16) c61.c123.L3.81 c123.L3.81 (1.3.81 + flufenacet (c123)) atrazine (c61) c77.c123.1.3.81 c123.L3.81 (1.3 .81 + flufenacet (d23)) terbuthylazine (c77) c63.c123.L3.81 c123.L3.81 (1.3.81 + flufenacet (d23)) bromoxynil (c63) c75.c123.L3.81 c123.L3 .81 (1.3.81 + flufenacet (d 23)) pyridate (c75) c62.c123.L3.81 c123.L3.81 (1.3.81 + flufenacet (d 23)) bentazone (c62) c73.c123.L3. 81 c123.L3.81 (1.3.81 + flufenacet (d 23)) metribuzin (c73) c1 16.c123.L3.81 c123.L3.81 (1.3.81 + flufenacet (d 23)) pendimethalin (c1 16) c61 .c1 10.L3.81 e 10.1.3.81 (1.3.81 + glyphosate-i. (c1 10)) atrazine (c61) c77.c1 10.1.3.81 d 10.1.3.81 (1.3.81 + glyphosate-i. (c1 10)) terbuthylazine (c77) c63.c1 10.L3.81 d 10.1.3.81 ( 1.3.81 + glyphosate-i. (C1 10)) bromoxynil (c63) c75.c1 10.1.3.81 d 10.1.3.81 (1.3.81 + glyphosate-i. (C1 10)) pyridate (c75) c62.c1 10.1. 3.81 d 10.1.3.81 (1.3.81 + glyphosate-i. (C1 10)) bentazone (c62) c73.c1 10.1.3.81 d 10.1.3.81 (1.3.81 + glyphosate-i. (C1 10)) metribuzin (c73 ) c116.c110.L3.81 d 10.1.3.81 (1.3.81 + glyphosate-i. (c110)) pendimethalin (c116) c61.c111.L3.81 d 11.1.3.81 (1.3.81 + glyphosate-t. (c111 ) Atrazine (c61) c77.c111.L3.81 d 11.1.3.81 (1.3.81 + Glyphosate-t (c111)) Terbuthylazine (c77) c63.c111.L3.81 d 11.1.3.81 (1.3.81 + Glyphosate-t (c111)) bromoxynil (c63) c75.c111.L3.81 d 11.1.3.81 (1.3.81 + glyphosate-t (c111)) pyridate (c75) c62.c111.l.3.81 d 11.1. 3.81 (1.3.81 + glyphosate-t. (C111)) bentazone (c62) c73.c111.L3.81 d 11.1.3.81 (1.3.81 + glyphosate-t. (C111)) metribuzin (c73) c116.c111. L3.81 d 11.1.3.81 (1.3.81 + glyphosate-t. (C111)) pendimethalin (c116) c61.c115.L3.81 c115.L3.81 (1.3.81 + glufosinate-a. (D 15)) Atrazine (c61) c77.c115.1.3.81 c115.L3.81 (1.3.81 + glufosinate-a. (D 15)) terbuthylazine (c77) c63.c115.L3.81 c115.L3.81 (1.3.81 + Glufosinate-a. (D 15)) bromoxynil (c63) c75.c115.1.3.81 c115.L3.81 (1.3.81 + glufosinate-a. (D 15)) pyridate (c75) c62.c115.1.3. 81 c115.L3.81 (1.3.81 + glufosinate-a. (D 15)) bentazone (c62) c73.c115 .1.3.81 c115.L3.81 (1.3.81 + glufosinate-a. (d 15)) metribuzin (c73) c116.c115.L3.81 c115.L3.81 (1.3.81 + glufosinate-a. (d 15)) pendimethalin (c116) c61.c112.L3.81 d 12.1.3.81 (1.3.81 + bialaphos (c112)) atrazine (c61) c77.c112.1.3.81 d 12.1.3.81 (1.3.81 + bialaphos (c112)) terbuthylazine (c77) c63.c112.L3.81 d 12.1.3.81 (1.3.81 + bialaphos (c112)) bromoxynil (c63) c75.c112.1.3.81 d 12.1.3.81 (1.3.81 + bialaphos (c112)) pyridate (c75) c62.c112.1.3.81 d 12.1.3.81 (1.3.81 + bialaphos (c112)) bentazone (c62) c73.c112.1.3.81 d 12.1.3.81 (1.3.81 + bialaphos (c112)) metribuzin (c73) c116.c112.L3.81 d 12.1.3.81 (1.3.81 + bialaphos (c112)) pendimethalin (c116) c61.c133.L3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) atrazine (c61) c77.c133.1.3. 81 c133.L3.81 (1.3.81 + 2,4-D (c133)) terbuthylazine (c77) c142.c133.1.3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) Diflufenzopyr (c142) c116.c133.L3.81 c133.L3.81 (1.3.81 + 2,4-D (c133)) pendimethalin (c116) c61.c138.L3.81 c138.L3.81 (1.3.81 + MCPA (c138)) atrazine (c61) c77.c138.L3.81 c138.L3.81 (1.3.81 + MCPA (c 138)) Terbuthylazine (c77) c142.c138.1.3.81 c138.L3.81 (1.3.81 + MCPA (c138)) Diflufenzopyr (c142) c116.c138.L3.81 c138.L3.81 (1.3.81 + MCPA (c138)) pendimethalin (c116) c61.c136.L3.81 c136.L3.81 (1.3.81 + Dicamba (c136)) atrazine (c61) c77.c136.L3.81 c136.L3.81 (1.3. 81 + Dicamba (c136)) Terbuthylazine (c77) c142.c136.1.3.81 c136.L3.81 (1.3.81 + Dicamba (c136)) Diflufenzopyr (c142) c116.c136.L3.81 c136.L3.81 ( 1.3.81 + dicamba (c136)) pendimethalin (c116) c61.c135.L3.81 d 35.1.3.81 (1.3.81 + clopyralid (c135)) atrazine (c61) c77.c135.L3.81 d 35.1.3.81 ( 1.3.81 + clopyralid (c135)) terbuthylazine (c77) c142.c135.1.3.81 d 35.1.3.81 (1.3.81 + clopyralid (c135)) diflufenzopyr (c142) c116.c135.L3.81 d 35.1.3.81 ( 1.3.81 + clopyralid (c135)) pendimethalin (c116) c61.c137.1.3.81 c137.L3.81 (1.3.81 + fluroxypyr (c137)) atrazine (c61) c77.c137.1.3.81 c137.L3. 81 (1.3.81 + fluroxypyr (d 37)) terbuthylazine (c77) c142.c137.1.3.81 c137.L3.81 (1.3.81 + fluroxypyr (c137)) diflufenzopyr (c142) c1 16.c137.L3.81 c137.L3.81 (1.3.81 + fluroxypyr (d 37)) Pendimethalin (c1 16) c61 .c141 .L3.81 c141 .1.3.81 (1.3.81 + aminocyclopyrachloro-atrazine (c61)
(c141 )) (c141))
c77.c141 .1.3.81 c141 .1.3.81 (1.3.81 + Aminocyclopyrachlor Terbuthylazin (c77)c77.c141 .1.3.81 c141 .1.3.81 (1.3.81 + aminocyclopyrachloroterbuthylazine (c77)
(c141 )) (c141))
c142.c141 .L3.81 c141 .1.3.81 (1.3.81 + Aminocyclopyrachlor Diflufenzopyr (c142)c142.c141 .L3.81 c141 .1.3.81 (1.3.81 + aminocyclopyrachlor diflufenzopyr (c142)
(c141 )) (c141))
c1 16.c141 .L3.81 c141 .1.3.81 (1.3.81 + Aminocyclopyrachlor Pendimethalin (c1 16)c1 16.c141 .L3.81 c141 .1.3.81 (1.3.81 + aminocyclopyrachlor pendimethalin (c1 16)
(c141 )) (c141))
Tabelle 42: In einer bevorzugten Ausgestaltungsform der Erfindung enthalten die Mischungen gemäß Tabelle 41 jeweils zusätzlich eine Komponente B, ausgewählt aus der Gruppe Cloquintocet, Mefenpyr, Fenchlorazol, Isoxadifen, Cyprosulfamid, Benoxa- cor, Dichlormid, Furilazol und 4-(Dichloracetyl)-1 -oxa-4-azaspiro[4.5]decan.Table 42: In a preferred embodiment of the invention, the mixtures according to Table 41 each additionally contain a component B selected from the group cloquintocet, mefenpyr, fenchlorazole, isoxadifen, cyprosulfamide, benoxa cor, dichloromide, furilazole and 4- (dichloroacetyl) -1 oxa-4-azaspiro [4.5] decane.
Tabelle 43: In einer besonders bevorzugten Ausgestaltungsform der Erfindung enthalten die Mischungen gemäß Tabelle 41 jeweils zusätzlich als Komponente B Cloquintocet (B2).Table 43: In a particularly preferred embodiment of the invention, the mixtures according to Table 41 each additionally contain, as component B, cloquintocet (B2).
Tabelle 44: In einer weiteren besonders bevorzugten Ausgestaltungsform der Erfindung enthalten die Mischungen gemäß Tabelle 41 jeweils zusätzlich als Komponente B Mefenpyr (B14). Tabelle 45: In einer weiteren besonders bevorzugten Ausgestaltungsform der Erfindung enthalten die Mischungen gemäß Tabelle 41 jeweils zusätzlich als Komponente B Isoxadifen (B13).Table 44: In a further particularly preferred embodiment of the invention, the mixtures according to Table 41 each additionally contain, as component B, Mefenpyr (B14). Table 45: In a further particularly preferred embodiment of the invention, the mixtures according to Table 41 each additionally contain, as component B, isoxadifen (B13).
Tabelle 46: Ein weiterer bevorzugter Gegenstand der vorliegenden Erfindung sind Mischungen, die sich von den Mischungen gemäß den Tabellen 41 bis 45, dadurch unterscheiden, dass sie als Komponente A) der Mischung das Benzoylpyrazol der Formel 1.1.81 , dass heißt die Verbindung der Formel I mitTable 46: Another preferred subject matter of the present invention are mixtures which differ from the mixtures according to Tables 41 to 45 in that as component A) of the mixture it is the benzoylpyrazole of the formula 1.1.81, that is the compound of the formula I with
R1 Methyl;R1 is methyl;
R2 Methyl;R2 is methyl;
R3 Methylsulfonyl;R3 is methylsulfonyl;
R4 Wasserstoff;R4 is hydrogen;
R5 Ethyl;R5 is ethyl;
R6 Wasserstoff; oder dessen landwirtschaftlich geeignetes Salz, enthalten.R6 is hydrogen; or its agriculturally suitable salt.
Tabelle 47: Die Mischungen gemäß den Tabellen 41 bis 46 eignen sich insbesondere für die Bekämpfung von Schadpflanzen in Maiskulturen.Table 47: The mixtures according to Tables 41 to 46 are particularly suitable for combating harmful plants in maize crops.
Die Komponenten der erfindungsgemäßen Mischung können gemeinsam, aber auch getrennt formuliert werden und/oder gemeinsam oder getrennt auf die Pflanzen, deren Lebensraum und/oder Samen ausgebracht werden. Bevorzugt werden die Wirkstoffe gleichzeitig appliziert. Es ist aber auch möglich, diese getrennt auszubringen.The components of the mixture according to the invention can be formulated together, but also separately, and / or applied together or separately to the plants, their habitat and / or seeds. Preferably, the active ingredients are applied simultaneously. But it is also possible to deploy them separately.
Die Erfindung betrifft auch Zusammensetzungen in Form eines als 1 - Komponentenzusammensetzung formulierten Pflanzenschutzmittels, enthaltend eine Wirkstoffkombination, die wenigstens ein Benzoylpyrazol der Formel I und wenigstens einen weiteren Wirkstoff und wenigstens einen festen oder flüssigen Träger und/oder eine oder mehrere grenzflächenaktive Substanzen und gewünschtenfalls einen oder mehrere für Pflanzenschutzmittel übliche weitere Hilfsstoffe.The invention also relates to compositions in the form of a plant protection composition formulated as a 1-component composition comprising a combination of active substances comprising at least one benzoylpyrazole of the formula I and at least one further active ingredient and at least one solid or liquid carrier and / or one or more surface-active substances and, if desired, one or more several other auxiliaries customary for pesticides.
Die Erfindung betrifft auch Zusammensetzungen in Form eines als 2- The invention also relates to compositions in the form of a 2-
Komponentenzusammensetzung formulierten Pflanzenschutzmittels, umfassend eine erste Komponente, enthaltend wenigstens ein Benzoylpyrazol der Formel I, einen festen oder flüssigen Träger und/oder eine oder mehrere grenzflächenaktive Substanzen, und eine zweite Komponente, enthaltend wenigstens einen weiteren Wirkstoff, einem festen oder flüssigen Träger und/oder eine oder mehrere grenzflächenaktive Substanzen, wobei zusätzlich beide Komponenten auch weitere, für Pflanzenschutzmittel üblichen Hilfsmittel enthalten können.Component composition formulated crop protection agent comprising a first component containing at least one Benzoylpyrazol of formula I, a solid or liquid carrier and / or one or more surfactants, and a second component containing at least one further active ingredient, a solid or liquid carrier and / or one or more surface-active substances, wherein in addition both components may also contain other, customary for crop protection agents.
In Zusammensetzungen, die wenigstens ein Benzoylpyrazol der Formel I als Kom- ponente A und wenigstens einen Safener B enthalten, liegt das Gewichtsverhältnis der Wirkstoffe A:B in der Regel im Bereich von 1 :1000 bis 1000:1 , vorzugsweise im Bereich von 1 :500 bis 500:1 , insbesondere im Bereich von 1 :250 bis 250:1 und besonders bevorzugt im Bereich von 1 :75 bis 75:1 . In Zusammensetzungen, die wenigstens ein Benzoylpyrazol der Formel I als Komponente A und wenigstens ein Herbizid C enthalten, liegt das Gewichtsverhältnis der Wirkstoffe A:C in der Regel im Bereich von 1 :1000 bis 1000:1 , vorzugsweise im Bereich von 1 :500 bis 500:1 , insbesondere im Bereich von 1 :250 bis 250:1 und besonders bevorzugt im Bereich von 1 :75 bis 75:1 .In compositions containing at least one benzoylpyrazole of the formula I as component A and at least one safener B, the weight ratio of the active compounds A: B is generally in the range from 1: 1000 to 1000: 1, preferably in the range from 1: 500 to 500: 1, in particular in the range of 1: 250 to 250: 1 and more preferably in the range of 1: 75 to 75: 1. In compositions containing at least one benzoylpyrazole of the formula I as component A and at least one herbicide C, the weight ratio of the active compounds A: C is generally in the range from 1: 1000 to 1000: 1, preferably in the range from 1: 500 to 500: 1, in particular in the range of 1: 250 to 250: 1 and more preferably in the range of 1: 75 to 75: 1.
In Zusammensetzungen, die sowohl wenigstens ein Benzoylpyrazol der Formel I als Komponente A, wenigstens einen Safener B und wenigstens ein Herbizid C enthalten, liegen die relativen Gewichtsanteile der Komponenten A:B in der Regel im Bereich von 1 :1000 bis 1000:1 , vorzugsweise im Bereich von 1 :500 bis 500:1 , insbesondere im Bereich von 1 :250 bis 250:1 und besonders bevorzugt im Bereich von 1 :75 bis 75:1 , das Gewichtsverhältnis der Komponente A:C in der Regel im Bereich von 1 :1000 bis 1000:1 , vorzugsweise im Bereich von 1 :500 bis 500:1 , insbesondere im Bereich von 1 :250 bis 250:1 und besonders bevorzugt im Bereich von 1 :75 bis 75:1 , und das Gewichtsverhältnis der Komponenten B:C in der Regel im Bereich von 1 :1000 bis 1000:1 , vorzugsweise im Bereich von 1 :500 bis 500:1 , insbesondere im Bereich von 1 :250 bis 250:1 und besonders bevorzugt im Bereich von 1 :75 bis 75:1 . Vorzugsweise liegt das Gewichtsverhältnis der Komponenten A + B zur Komponente C im Bereich von 1 :500 bis 500:1 , insbesondere im Bereich von 1 :250 bis 250:1 und besonders bevorzugt im Bereich von 1 :75 bis 75:1 .In compositions containing both at least one benzoylpyrazole of the formula I as component A, at least one safener B and at least one herbicide C, the relative proportions by weight of the components A: B are generally in the range from 1: 1000 to 1000: 1, preferably in the range from 1: 500 to 500: 1, in particular in the range from 1: 250 to 250: 1 and more preferably in the range from 1: 75 to 75: 1, the weight ratio of component A: C is generally in the range of 1 : 1000 to 1000: 1, preferably in the range of 1: 500 to 500: 1, in particular in the range of 1: 250 to 250: 1 and more preferably in the range of 1: 75 to 75: 1, and the weight ratio of the components B: C usually in the range of 1: 1000 to 1000: 1, preferably in the range of 1: 500 to 500: 1, in particular in the range of 1: 250 to 250: 1 and particularly preferably in the range of 1: 75 to 75: 1. The weight ratio of components A + B to component C is preferably in the range from 1: 500 to 500: 1, in particular in the range from 1: 250 to 250: 1 and particularly preferably in the range from 1: 75 to 75: 1.
In Zusammensetzungen, die wenigstens ein Benzoylpyrazol der Formel I als Kom- ponente A und zwei Herbizide C (Ca und Cb) enthalten, liegt das Gewichtsverhältnis der Wirkstoffe A:Ca und A:Cb in der Regel unabhängig voneinander jeweils im Bereich von 1 :1000 bis 1000:1 , vorzugsweise im Bereich von 1 :500 bis 500:1 , insbesondere im Bereich von 1 :250 bis 250:1 und besonders bevorzugt im Bereich von 1 :75 bis 75:1. Die Wirkstoffe in den beschriebenen Zusammensetzungen liegen jeweils vorzugsweise in synergistisch wirksamen Mengen vor.In compositions which comprise at least one benzoylpyrazole of the formula I as component A and two herbicides C (Ca and Cb ), the weight ratio of the active compounds A: Ca and A: Cb is generally in the range independently of one another from 1: 1000 to 1000: 1, preferably in the range of 1: 500 to 500: 1, in particular in the range of 1: 250 to 250: 1 and more preferably in the range of 1: 75 to 75: 1. The active ingredients in the described compositions are each preferably present in synergistically effective amounts.
Die Benzoylpyrazole der Formel I und die erfindungsgemäßen Mischungen können auch eine pflanzenstärkende Wirkung aufweisen. Sie eigenen sich daher zu Mobilisie- rung pflanzeneigener Abwehrkräfte gegen Befall durch unerwünschte Mikroorganismen, wie Schadpilze, aber auch Viren und Bakterien. Unter pflanzenstärkenden (resistenzinduzierenden) Stoffen sind in diesem Zusammenhang solche Substanzen zu verstehen, die in der Lage sind, das Abwehrsystem von behandelten Pflanzen so zu stimulieren, dass diese bei nachfolgender Inokulation mit unerwünschten Mikroorganis- men weitgehende Resistenz gegen diese Mikroorganismen entfalten.The benzoylpyrazoles of the formula I and the mixtures according to the invention may also have a plant-strengthening effect. They are therefore suitable for mobilizing plant-specific defenses against attack by undesired microorganisms, such as harmful fungi, but also viruses and bacteria. In this context, plant-strengthening (resistance-inducing) substances are to be understood as meaning those substances which are capable of stimulating the defense system of treated plants in such a way that they develop extensive resistance to these microorganisms during subsequent inoculation with undesired microorganisms.
Die Benzoylpyrazole der Formel I und die erfindungsgemäßen Mischungen können eingesetzt werden, um Pflanzen innerhalb eines gewissen Zeitraumes nach der Behandlung gegen den Befall durch unerwünschte Mikroorganismen zu schützen. Der Zeitraum, innerhalb dessen Schutz herbeigeführt wird, erstreckt sich im Allgemeinen auf 1 bis 28 Tage, vorzugsweise 1 bis 14 Tage nach der Behandlung der Pflanzen mit den Benzoylpyrazole der Formel I bzw. nach Behandlung des Saatguts, auf bis zu 9 Monate nach Aussaat. The benzoylpyrazoles of the formula I and the mixtures according to the invention can be used to protect plants against attack by undesired microorganisms within a certain period of time after the treatment. The period within which protection is provided generally extends to 1 to 28 days, preferably 1 to 14 days after the treatment of the plants with the benzoylpyrazoles of the formula I or after treatment of the seed, for up to 9 months after sowing.
Die Benzoylpyrazole der Formel I und die erfindungsgemäßen Mischungen eignen sich auch zur Steigerung des Ernteertrages. The benzoylpyrazoles of the formula I and the mixtures according to the invention are also suitable for increasing the crop yield.
Sie sind außerdem mindertoxisch und weisen eine gute Pflanzenverträglichkeit auf. They are also low toxicity and have good plant tolerance.
In Abhängigkeit von der jeweiligen Applikationsmethode können die Benzoylpyrazole der Formel I und die erfindungsgemäßen Mischungen, insbesondere die bevorzugten Ausgestaltungen davon, bzw. sie enthaltende Mittel noch in einer weiteren Zahl von Kulturpflanzen zur Beseitigung unerwünschter Pflanzen eingesetzt werden. In Betracht kommen beispielsweise folgende Kulturen: Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus li- mon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sa- tivus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Manihot esculenta, Medicago sativa, Musa spec, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis und pru- nus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Seeale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.Depending on the particular application method, the benzoylpyrazoles of the formula I and the mixtures according to the invention, in particular the preferred embodiments thereof, or agents containing them, can be used in a further number of crop plants for the removal of undesired plants. For example, the following cultures may be considered: Allium cepa, pineapple comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapeseed, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus lichen, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea Liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Seeale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.
Der Begriff Kulturpflanzen schließt auch solche ein, die durch Züchtung, Mutagenese oder gentechnische Methoden verändert wurden. Gentechnisch veränderte Pflanzen sind Pflanzen, deren genetisches Material in einer Weise verändert worden ist, wie sie unter natürlichen Bedingungen durch Kreuzen, Mutationen oder natürliche Rekombination (d.h. Neuzusammenstellung der Erbinformation) nicht vorkommt. Dabei werden in der Regel ein oder mehrere Gene in das Erbgut der Pflanze integriert, um die Eigen- Schäften der Pflanze zu verbessern.The term crops also includes those that have been modified by breeding, mutagenesis or genetic engineering methods. Genetically engineered plants are plants whose genetic material has been altered in a manner that does not occur under natural conditions by crossing, mutations or natural recombination (i.e., rearrangement of genetic information). As a rule, one or more genes are integrated into the genome of the plant in order to improve the properties of the plant.
Der Begriff Kulturpflanzen umfasst somit auch Pflanzen, die durch züchterische und gentechnische Maßnahmen eine Toleranz gegen bestimmter Herbizidklassen, wie Hydroxyphenylpyruvat-Dioxygenase (HPPD)-Inhibitoren, Acetolactat-Synthase (ALS)- Inhibitoren, wie z.B. Sulfonylharnstoffe (EP-A-0257993, US5,013,659) oder Imidazoli- none (siehe z.B. US6,222,100, WO01/82685, WO00/26390, W097/41218, The term crops thus also encompasses plants which, by breeding and genetic engineering measures, tolerate certain classes of herbicides, such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) inhibitors, e.g. Sulfonylureas (EP-A-0257993, US5,013,659) or imidazolinones (see for example US6,222,100, WO01 / 82685, WO00 / 26390, WO97 / 41218,
WO98/02526, WO98/02527, WO04/106529, WO05/20673, WO03/14357,WO98 / 02526, WO98 / 02527, WO04 / 106529, WO05 / 20673, WO03 / 14357,
WO03/13225, WO03/14356, WO04/16073), Enolpyruvylshikimat-3-Phosphat-Synthase (EPSPS)-lnhibitoren wie z.B. Glyphosate (siehe z.B. WO92/00377), Glutaminsyntheta- se (GS)-lnhibitoren wie z.B. Glufosinat (siehe z.B. EP-A-0242236, EP-A-242246) oder Oxynil-Herbizide (siehe z.B. US5,559,024) erworben haben.WO03 / 13225, WO03 / 14356, WO04 / 16073), enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, e.g. Glyphosate (see, for example, WO92 / 00377), glutamine synthetase (GS) inhibitors, e.g. Glufosinate (see, e.g., EP-A-0242236, EP-A-242246) or oxynil herbicides (see, e.g., U.S. 5,559,024).
Mit Hilfe klassischer Züchtungsmethoden (Mutagenese) wurden zahlreiche Kulturpflanzen, z.B. Clearfield®-Raps, erzeugt, die eine Toleranz gegen Imidazolinone, z.B. Imazamox, haben. Mit Hilfe gentechnischer Methoden wurden Kulturpflanzen, wie Soja, Baumwolle, Mais, Rüben und Raps, erzeugt, die resistent gegen Glyphosate oder Glufosinat sind, erzeugt, welche unter den Handelsnamen RoudupReady® (Glyphosate) und Liberty Link® (Glufosinate) erhältlich sind. Der Begriff Kulturpflanzen umfasst somit auch Pflanzen, die mit Hilfe gentechnischer Maßnahmen ein oder mehrere Toxine, z.B. solche aus dem Bakterienstamm Bacillus ssp., produzieren. Toxine, die durch solche gentechnisch veränderten Pflanzen hergestellt werden, umfassen z.B. Insektizide Proteine von Bacillus spp., insbesondere von B. thuringiensis, wie die Endotoxine CrylAb, CrylAc, Cryl F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 , Cry9c, Cry34Ab1 oder Cry35Ab1 ; oder vegetative Insektizide Proteine (VIPs), z.B. VIP1 , VIP2, VIP3, oder VIP3A; Insektizide Proteine von Nematoden- kolonisierenden Bakterien, z.B. Photorhabdus spp. oder Xenorhabdus spp.; Toxine aus tierischen Organismen, z.B. Wespen-, Spinnen- oder Skorpionstoxine; pilzliche Toxine, z.B. aus Streptomyceten; pflanzliche Lektine, z.B. aus Erbse oder Gerste; Agglutinine; Proteinase-Inhibitoren, z.B. Trypsin-Inhibitoren, Serinprotease-Inhibitoren, Patatin, Cystatin oder Papain-Inhibitoren; Ribosomen-inaktivierende Proteine (RIPs), z.B. Ricin, Mais-RIP, Abrin, Luffin, Saporin oder Bryodin; Steroid-metabolisierende Enzyme, z.B. 3-Hydroxysteroid-Oxidase, Ecdysteroid-IDP-Glycosyl-Transferase, Cholesterinoxidase, Ecdyson-Inhibitoren oder HMG-CoA-Reduktase; lonenkanalblocker, z.B. Inhibitoren von Natrium- oder Calziumkanalen; Juvenilhormon-Esterase; Rezeptoren für das diure- tischen Hormon (Helicokininrezeptoren); Stilbensynthase, Bibenzylsynthase, Chitin- asen und Glucanasen. Diese Toxine können in den Pflanzen auch als Prätoxine, Hybridproteine, verkürzte oder anderweitig modifizierte Proteine produziert werden. Hyb- ridproteine zeichnen sich durch eine neue Kombination von verschiedenen Proteindomänen aus (siehe z.B. WO2002/015701 ). Weitere Beispiele für derartige Toxine oder gentechnisch veränderte Pflanzen, die diese Toxine produzieren, sind in EP-A374753, WO93/007278, W095/34656, EP-A427529, EP-A451878, WO03/018810 undUsing classical breeding methods (mutagenesis) were produced numerous crops, including Clearfield® canola, which have a tolerance to imidazolinones, eg imazamox. With Crop plants were as soybeans, cotton, corn, beets and oilseed rape were generated which are resistant to glyphosate or glufosinate, and sold under the trade name RoudupReady® (glyphosate) and Liberty Link® (glufosinate) are available. The term crops thus also includes plants which produce one or more toxins, for example those from the bacterial strain Bacillus ssp., By means of genetic engineering. Toxins produced by such genetically modified plants include, for example, insecticides proteins of Bacillus spp., In particular B. thuringiensis, such as the endotoxins CrylAb, CrylAc, Cryl F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9c, Cry34Ab1 or Cry35Ab1 ; or vegetative insecticidal proteins (VIPs), eg VIP1, VIP2, VIP3, or VIP3A; Insecticidal proteins of nematode-colonizing bacteria, eg, Photorhabdus spp. or Xenorhabdus spp .; Toxins from animal organisms, eg wasp, spider or scorpion toxins; fungal toxins, eg from streptomycetes; vegetable lectins, for example from pea or barley; agglutinins; Proteinase inhibitors, eg trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; Ribosome-inactivating proteins (RIPs), eg ricin, maize RIP, abrin, luffin, saporin or bryodin; Steroid metabolizing enzymes, eg 3-hydroxysteroid oxidase, ecdysteroid IDP glycosyltransferase, cholesterol oxidase, ecdysone inhibitors or HMG-CoA reductase; ion channel blockers, eg inhibitors of sodium or calcium channels; Juvenile hormone esterase; Receptors for the diuretic hormone (helicokinin receptors); Stilbene synthase, bibenzyl synthase, chitinases and glucanases. These toxins can also be produced in the plants as proteoxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are distinguished by a novel combination of different protein domains (see, for example, WO2002 / 015701). Further examples of such toxins or genetically engineered plants that produce these toxins are described in EP-A374753, WO93 / 007278, WO95 / 34656, EP-A-427529, EP-A451878, WO03 / 018810 and EP-A-0 438 9
WO03/052073 offenbart. Die Methoden zur Herstellung dieser gentechnisch veränder- ten Pflanzen sind dem Fachmann bekannt und z.B. in den oben erwähnten Publikationen dargelegt. Zahlreiche der zuvor genannten Toxine verleihen den Pflanzen, die diese produzieren, eine Toleranz gegen Schädlinge aus allen taxonomischen Arthropo- denklassen, insbesondere gegen Käfer (Coleoptera), Zweiflügler (Diptera) undWO03 / 052073. The methods for the production of these genetically modified plants are known to the person skilled in the art and are described e.g. in the publications mentioned above. Numerous of the abovementioned toxins confer on the plants which produce them a tolerance to pests of all taxonomic arthropod classes, in particular to beetles (Coleoptera), diptera (Diptera) and
Schmetterlinge (Lepidoptera) und gegen Nematoden (Nematoda).Butterflies (Lepidoptera) and nematodes (Nematoda).
Gentechnisch veränderte Pflanzen, die ein oder mehrere Gene, die für Insektizide Toxine kodieren, produzieren sind z.B. in den oben erwähnten Publikationen beschrieben und zum Teil kommerziell erhältlich, wie z.B. YieldGard® (Maissorten, die das Toxin CrylAb produzieren), YieldGard® Plus (Maissorten, die die Toxine CrylAb und Cry3Bb1 produzieren), Starlink® (Maissorten, die das Toxin Cry9c produzieren), Hercu- lex® RW (Maissorten, die die Toxine Cry34Ab1 , Cry35Ab1 und das Enzym Phosphi- nothricin-N-Acetyltransferase [PAT] produzieren); NuCOTN® 33B (Baumwollsorten, die das Toxin CrylAc produzieren), Bollgard® I (Baumwollsorten, die das Toxin CrylAc produzieren), Bollgard® II (Baumwollsorten, die die Toxine CrylAc und Cry2Ab2 produzieren); VIPCOT® (Baumwollsorten, die ein VIP-Toxin produzieren); NewLeaf® (Kartof- felsorten, die das Toxin Cry3A produzieren); Bt-Xtra®, NatureGard®, KnockOut®, Bite- Gard®, Protecta®, Bt1 1 (z. B. Agrisure® CB) und Bt176 von Syngenta Seeds SAS, Frankreich, (Maissorten, die das Toxin CrylAb und das PAT-Enyzm produzieren), MIR604 von Syngenta Seeds SAS, Frankreich (Maissorten, die ein modifizierte Version des Toxins Cry3A produzieren, siehe hierzu WO03/018810), MON863 von Monsanto Europe S.A., Belgien (Maissorten, die das Toxin Cry3Bb1 produzieren), IPC531 von Monsanto Europe S.A., Belgien (Baumwollsorten, die eine modifizierte Version des Toxins CrylAc produzieren) und 1507 von Pioneer Overseas Corporation, Belgien (Maissorten, die das Toxin Cryl F und das PAT-Enyzm produzieren).Genetically engineered plants which have one or more genes that encode toxins of insecticides which produce, for example, described in the above mentioned publications and some are commercially available such as YieldGard® (corn cultivars producing the toxin CrylAb), YieldGard® Plus (corn varieties that produce the toxins CrylAb and Cry3Bb1), StarLink® (corn cultivars producing the toxin Cry9c), which produce the toxins Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin nothricin-N-acetyltransferase [PAT] Hercu- lex® RW (corn cultivars ); NuCOTN® 33B (cotton cultivars producing the toxin CrylAc), Bollgard® I (cotton cultivars producing the toxin CrylAc), Bollgard® II (cotton cultivars producing the toxins CrylAc and Cry2Ab2); VIPCOT® (cotton varieties that produce a VIP toxin); NewLeaf® (potato rock cultivars producing the Cry3A toxin); Bt Xtra®, NatureGard®®, KnockOut®, BITE Gard®, Protecta®, Bt1 1 (z. B. Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France (corn varieties which the toxin CrylAb and the PAT Produce enzyme), MIR604 from Syngenta Seeds SAS, France (maize varieties producing a modified version of the toxin Cry3A, see WO03 / 018810), MON863 from Monsanto Europe SA, Belgium (maize varieties producing the toxin Cry3Bb1), IPC531 from Monsanto Europe SA, Belgium (Cotton varieties that produce a modified version of the toxin CrylAc) and 1507 from Pioneer Overseas Corporation, Belgium (maize varieties that produce the toxin Cryl F and the PAT enzyme).
Der Begriff Kulturpflanzen umfasst somit auch Pflanzen, die mit Hilfe gentechnischer Maßnahmen ein oder mehrere Proteine produzieren, die eine erhöhte Resistenz oder Widerstandfähigkeit gegen bakterielle, virale oder pilzliche Pathogene bewirken, wie z.B. sogenannte Pathogenesis-related-Proteine (PR-Proteine, siehe EP-A0392225), Resistenzproteine (z.B. Kartoffelsorten, die zwei Resistenzgene gegen Phytophthora infestans aus der mexikanischen Wildkartoffel Solanum bulbocastanum produzieren) oder T4-Lysozym (z.B. Kartoffelsorten, die durch die Produktion diese Proteins resistent gegen Bakterien wie Erwinia amylvora ist). The term crops thus also encompasses plants which, by means of genetic engineering, produce one or more proteins which bring about increased resistance or resistance to bacterial, viral or fungal pathogens, e.g. so-called pathogenesis-related proteins (PR proteins, see EP-A0392225), resistance proteins (eg potato varieties that produce two resistance genes against Phytophthora infestans from the Mexican wild potato Solanum bulbocastanum) or T4 lysozyme (eg potato varieties produced by the production of this protein resistant to bacteria such as Erwinia amylvora).
Der Begriff Kulturpflanzen umfasst somit auch Pflanzen, deren Produktivität mit Hilfe gentechnischer Methoden verbessert wurde, indem z.B. die Ertragsfähigkeit (z.B. Biomasse, Kornertrag, Stärke-, Öl- oder Proteingehalt), die Toleranz gegenüber Trockenheit, Salz oder anderen begrenzenden Umweltfaktoren oder die Widerstandsfähigkeit gegenüber Schädlingen und pilzlichen, bakteriellen und viralen Pathogenen gesteigert wird. The term crops thus also includes plants whose productivity has been improved by genetic engineering methods, e.g. productivity (e.g., biomass, grain yield, starch, oil or protein content), tolerance to drought, salt or other limiting environmental factors or resistance to pests and fungal, bacterial and viral pathogens is increased.
Der Begriff Kulturpflanzen umfasst auch Pflanzen, deren Inhaltsstoffe insbesondere zur Verbesserung der menschlichen oder tierischen Ernährung mit Hilfe gentechnischer Methoden verändert wurden, indem z.B. Ölpflanzen gesundheitsfördernde lang- kettige Omega-3-Fettsäuren oder einfach ungesättigte Omega-9-Fettsäuren (z.B. Ne- xera®-Raps) produzieren.The term crop plants also includes plants whose ingredients particular to improve human or animal nutrition using genetic engineering methods have been changed by, for example oil plants producing health long-chain omega-3 fatty acids or monounsaturated omega-9 fatty acids (eg Ne xera® Oilseed rape).
Der Begriff Kulturpflanzen umfasst auch Pflanzen, die zur verbesserten Produktion von Rohstoffen mit Hilfe gentechnischer Methoden verändert wurden, indem z.B. der Amylopektin-Gehalt von Kartoffeln (Amflora®-Kartoffel) erhöht wurde.The term also includes crop plants that have been modified for improved production of raw materials with the aid of recombinant methods by, for example, the amylopectin content of potatoes (Amflora® potato) increased.
Des Weiteren wurde gefunden, dass die Benzoylpyrazole der Formel I und die erfin- dungsgemäßen Mischungen auch zur Defoliation und/oder Desikkation von Pflanzenteilen geeignet ist, wofür Kulturpflanzen wie Baumwolle, Kartoffel, Raps, Sonnenblume, Sojabohne oder Ackerbohnen, insbesondere Baumwolle, in Betracht kommen. Diesbezüglich wurden Mittel zur Desikkation und /oder Defoliation von Pflanzen, Verfahren zur Herstellung dieser Mittel und Verfahren zur Desikkation und/oder Defoliation von Pflan- zen mit den Benzoylpyrazolen der Formel I gefunden. Furthermore, it has been found that the benzoylpyrazoles of the formula I and the mixtures according to the invention are also suitable for the defoliation and / or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, come into consideration , In this regard, there have been found compositions for the desiccation and / or defoliation of plants, processes for the preparation of these compositions and processes for the desiccation and / or defoliation of plants with the benzoylpyrazoles of the formula I.
Als Desikkantien eignen sich die Benzoylpyrazole der Formel I und die erfindungsgemäßen Mischungen insbesondere zur Austrocknung der oberirdischen Teile von Kulturpflanzen wie Kartoffel, Raps, Sonnenblume und Sojabohne aber auch Getreide. Damit wird ein vollständig mechanisches Beernten dieser wichtigen Kulturpflanzen ermöglicht. Von wirtschaftlichem Interesse ist ferner die Ernteerleichterung, die durch das zeitlich konzentrierte Abfallen oder Vermindern der Haftfestigkeit am Baum bei Zitrusfrüchten, Oliven oder bei anderen Arten und Sorten von Kern-, Stein- und Schalenobst ermöglicht wird. Derselbe Mechanismus, d.h., die Förderung der Ausbildung von Trenn- gewebe zwischen Frucht- oder Blatt- und Sprossteil der Pflanzen ist auch für ein gut kontrollierbares Entblättern von Nutzpflanzen, insbesondere Baumwolle, wesentlich.Suitable desiccants are the benzoylpyrazoles of the formula I and the mixtures according to the invention, in particular for dehydration of the aerial parts of crop plants such as potato, rape, sunflower and soybean, but also cereals. This allows a completely mechanical harvesting of these important crops. Of economic interest is also the harvest relief, which is made possible by the time-concentrated dropping or reducing the adhesion to the tree in citrus fruits, olives or other types and varieties of pome, stone and peel fruit. The same mechanism, ie the promotion of the formation of separating tissue between fruit or leaf and shoot part of the plants is also essential for a well controllable defoliation of crops, especially cotton.
Außerdem führt die Verkürzung des Zeitintervalls, in dem die einzelnen Baumwollpflanzen reif werden, zu einer erhöhten Qualität der Faser nach der Ernte. Die Benzoylpyrazole der Formel I und die erfindungsgemäßen Mischungen bzw. die sie enthaltenden herbiziden Mittel können beispielsweise in Form von direkt versprühbaren wäßrigen Lösungen, Pulvern, Suspensionen, auch hochprozentigen wäßrigen, öligen oder sonstigen Suspensionen oder Dispersionen, Emulsionen, Öldispersionen, Pasten, Stäubemitteln, Streumitteln oder Granulaten durch Versprühen, Vernebeln, Verstäuben, Verstreuen, Gießen oder Behandlung des Saatgutes bzw. Mischen mit dem Saatgut angewendet werden. Die Anwendungsformen richten sich nach den Verwendungszwecken; sie sollten in jedem Fall möglichst die feinste Verteilung der erfindungsgemäßen Wirkstoffe gewährleisten.In addition, shortening the time interval in which the individual cotton plants ripen results in increased fiber quality after harvest. The benzoylpyrazoles of the formula I and the mixtures according to the invention or the herbicidal compositions containing them can be used, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, even high-percentage aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents or granules are applied by spraying, atomizing, dusting, scattering, pouring or treatment of the seed or mixing with the seed. The forms of application depend on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.
Die herbiziden Mittel enthalten eine herbizid wirksame Menge mindestens eines Benzoylpyrazoles der Formel I oder eines landwirtschaftlich brauchbaren Salzes von I oder die erfindungsgemäßen Mischungen und für die Formulierung von Pflanzenschutzmitteln übliche Hilfsstoffe. The herbicidal compositions contain a herbicidally effective amount of at least one Benzoylpyrazoles of formula I or an agriculturally useful salt of I or the mixtures according to the invention and for the formulation of pesticides usual excipients.
Beispiele für die Formulierung von Pflanzenschutzmitteln übliche Hilfsmittel sind i- nerte Hilfsstoffe, feste Trägerstoffe, oberflächenaktive Stoffe (wie Dispergiermittel Schutzkolloide, Emulgatoren, Netzmittel und Haftmittel), organische und anorganische Verdicker, Bakterizide, Frostschutzmittel, Entschäumer ggf. Farbstoffe und für Saatgutformulierungen Kleber. Examples of the Formulation of Pesticides Commonly used auxiliaries are preferred auxiliaries, solid carriers, surface-active substances (such as dispersants, protective colloids, emulsifiers, wetting agents and adhesives), organic and inorganic thickeners, bactericides, antifreeze agents, defoamers, if necessary, dyes and for seed formulations adhesives.
Beispiele für Verdicker (d.h. Verbindungen, die der Formulierung ein modifiziertes Fließverhalten verleihen, d.h. hohe Viskosität im Ruhezustand und niedrige Viskosität im bewegten Zustand) sind Polysaccharide wie Xanthan Gum (Kelzan® der Fa. Kelco), Rhodopol® 23 (Rhone Poulenc) oder Veegum® (Firma R.T. Vanderbilt) sowie organische und anorganische Schichtmineralien wie Attaclay® (Firma Engelhardt). Examples of thickeners (ie, compounds which impart modified flowability to the formulation, ie, high-level at low viscosity and low viscosity in the agitated state) are polysaccharides such as xanthan gum (Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum ® (company RT Vanderbilt) and organic and inorganic layer minerals such as Attaclay® (Engelhardt).
Beispiele für Antischaummittel sind Silikonemulsionen (wie z.Bsp. Silikon® SRE, Firma Wacker oder Rhodorsil® der Firma Rhodia ), langkettige Alkohole, Fettsäuren, Salze von Fettsäuren, fluororganische Verbindungen und deren Gemische. Examples of antifoams are silicone emulsions (such as, for example, Silikon® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.
Bakterizide können zur Stabilisierung der wäßrigen Herbizid-Formulierung zugesetzt werden. Beispiele für Bakterizide sind Bakterizide basierend auf Diclorophen und Ben- zylalkoholhemiformal (Proxel® der Fa. ICI oder Acticide® RS der Fa. Thor Chemie und Kathon® MK der Firma Rohm & Haas) sowie Isothiazolinonderivaten wie Alkylisothia- zolinonen und Benzisothiazolinonen (Acticide MBS der Fa. Thor Chemie) Bactericides may be added to stabilize the aqueous herbicidal formulation. Examples of bactericides are bactericides based on diclorophene and benzyl alcohol hemiformal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas) and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS der Fa. Thor Chemie)
Beispiele für Frostschutzmittel sind Ethylenglycol, Propylenglycol, Harnstoff oder Glycerin. Beispiele für Farbmittel sind sowohl in Wasser wenig lösliche Pigmente als auch in Wasser lösliche Farbstoffe. Als Beispiele genannt seien die unter den Bezeichnungen Rhodamin B, C.l. Pigment Red 1 12 und C.l. Solvent Red 1 bekannten Farbstoffe, sowie pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pig- ment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 1 12, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.Examples of antifreeze agents are ethylene glycol, propylene glycol, urea or glycerol. Examples of colorants are both water-insoluble pigments and water-soluble dyes. Examples which may be mentioned are the dyes known under the names Rhodamine B, Cl Pigment Red 1 12 and Cl Solvent Red 1, and pigment blue 15: 4, pigment blue 15: 3, pigment blue 15: 2, pigment blue 15: 1, pig pigment blue 1, pigment red 1, pigment red 48: 2, pigment red 48: 1, pigment red 57: 1, pigment red 53: 1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
Beispiele für Kleber sind Polyvinylpyrrolidon, Polyvinylacetat, Polyvinylalkohol und Tylose. Examples of adhesives are polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
Als inerte Zusatzstoffe kommen beispielsweise in Betracht:Suitable inert additives are, for example:
Mineralölfraktionen von mittlerem bis hohem Siedepunkt, wie Kerosin oder Dieselöl, ferner Kohlenteeröle sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aromatische Kohlenwasserstoffe, z.B. Paraffin, Tetrahydronaphthalin, alkylierte Naphthaline oder deren Derivate, alkylierte Benzole oder deren Derivate, Alkohole wie Methanol, Ethanol, Propanol, Butanol, Cyclohexanol, Ketone wie Cyclo- hexanon oder stark polare Lösungsmittel, z. B. Amine wie N-Methylpyrrolidon oder Wasser. Mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol, cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, eg. As amines such as N-methylpyrrolidone or water.
Feste Trägerstoffe sind Mineralerden wie Kieselsäuren, Kieselgele, Silikate, Talkum, Kaolin, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, Düngemittel, wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Pro- dukte wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver oder andere feste Trägerstoffe. Solid carriers are mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
Als oberflächenaktive Stoffe (Adjuvantien, Netz-, Haft-, Dispergier- sowie Emulgiermittel) kommen die Alkali-, Erdalkali-, Ammoniumsalze von aromatischen Sulfonsäu- ren, z.B. Ligninsulfonsäuren (z.B. Borrespers-Typen, Borregaard), Phenolsulfonsäuren, Naphthalinsulfonsäuren (Morwet-Typen, Akzo Nobel) und Dibutylnaphthalinsulfonsäure (Nekal-Typen, BASF SE), sowie von Fettsäuren, Alkyl- und Alkylarylsulfonaten, Alkyl-, Laurylether- und Fettalkoholsulfaten, sowie Salze sulfatierter Hexa-, Hepta- und Octa- decanolen sowie von Fettalkoholglykolether, Kondensationsprodukte von sulfoniertem Naphthalin und seiner Derivate mit Formaldehyd, Kondensationsprodukte des Naph- thalins bzw. der Naphthalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxyethyle- noctylphenolether, ethoxyliertes Isooctyl-, Octyl- oder Nonylphenol, Alkylphenyl-, Tribu- tylphenylpolyglykolether, Alkylarylpolyetheralkohole, Isotridecylalkohol, Fettalkoholethy- lenoxid-Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylenalkylether oder Polyo- xypropylenalkylether, Laurylalkoholpolyglykoletheracetat, Sorbitester, Lignin- Sulfitablaugen sowie Proteine, denaturierte Proteine, Polysaccharide (z.B. Methylcellu- lose), hydrophob modifizierte Stärken, Polyvinylalkohol (Mowiol Typen Clariant), Poly- carboxylate (BASF SE, Sokalan-Typen), Polyalkoxylate, Polyvinylamin (BASF SE, Lu- pamin-Typen), Polyethylenimin (BASF SE, Lupasol-Typen), Polyvinylpyrrolidon und deren Copolymere in Betracht.As surface-active substances (adjuvants, wetting agents, adhesives, dispersants and emulsifiers), the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, eg lignosulfonic acids (eg Borrespers types, Borregaard), phenolsulfonic acids, naphthalenesulfonic acids (Morwet types , Akzo Nobel) and dibutylnaphthalenesulfonic acid (Nekal types, BASF SE), as well as fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethyl toctylphenol ethers, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, tributylphenyl polyglycol ethers, alkylarylpolyether alcohols, isotridecyl alcohol, fatty alcohol ethylenoxide Condensates, ethoxylated castor oil, polyoxyethyleneal alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin liquors and proteins, denatured proteins, polysaccharides (eg methyl cellulose), hydrophobically modified starches, polyvinyl alcohol (Mowiol types Clariant), polycarboxylates (BASF SE, Sokalan types), Polyalkoxylates, polyvinylamine (BASF SE, Lu pamin types), polyethylenimine (BASF SE, Lupasol types), polyvinylpyrrolidone and copolymers thereof.
Pulver-, Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermählen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden. Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
Granulate, z.B. Umhüllungs-, Imprägnierungs- und Homogengranulate können durch Bindung der Wirkstoffe an feste Trägerstoffe hergestellt werden. Granules, e.g. Coating, impregnation and homogeneous granules can be prepared by binding the active compounds to solid carriers.
Wässrige Anwendungsformen können aus Emulsionskonzentraten, Suspensionen, Pasten, netzbaren Pulvern oder wasserdispergierbaren Granulaten durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Öldispersionen können die Verbindungen der Formel I als solche oder in einem Öl oder Lösungsmittel gelöst, mittels Netz-, Haft-, Dispergier- oder Emulgiermittel in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz, Netz-, Haft-, Dispergier- oder Emulgiermittel und eventuell Lösungsmittel oder Öl bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind. Aqueous application forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. For the preparation of emulsions, pastes or oil dispersions, the compounds of the formula I as such or dissolved in an oil or solvent, can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier. However, it is also possible to prepare concentrates consisting of active substance, wetting, adhesion, dispersing or emulsifying agent and possibly solvent or oil, which are suitable for dilution with water.
Die Konzentrationen der Benzoylpyrazole der Formel I in den anwendungsfertigen Zubereitungen können in weiten Bereichen variiert werden. Die Formulierungen enthalten im Allgemeinen 0,001 bis 98 Gew.-%, vorzugsweise 0,01 bis 95 Gew.-%, mindestens eines Wirkstoffs. Die Wirkstoffe werden dabei in einer Reinheit von 90% bis 100%, vorzugsweise 95% bis 100% (nach NMR-Spektrum) eingesetzt. The concentrations of the benzoylpyrazoles of the formula I in the ready-to-use formulations can be varied within wide limits. The formulations generally contain from 0.001 to 98% by weight, preferably from 0.01 to 95% by weight, of at least one active ingredient. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
Die erfindungsgemäßen Benzoylpyrazole der Formel I können beispielsweise wie folgt formuliert werden:The benzoylpyrazoles of the formula I according to the invention can be formulated, for example, as follows:
1. Produkte zur Verdünnung in Wasser 1. Products for dilution in water
A Wasserlösliche Konzentrate A Water-soluble concentrates
10 Gew.-Teile Wirkstoff werden mit 90 Gew.-Teilen Wasser oder einem wasserlöslichen Lösungsmittel gelöst. Alternativ werden Netzmittel oder andere Hilfsmittel zugefügt. Bei der Verdünnung in Wasser löst sich der Wirkstoff. Man erhält auf diese Weise eine Formulierung mit 10 Gew.-% Wirkstoffgehalt.10 parts by weight of active compound are dissolved with 90 parts by weight of water or a water-soluble solvent. Alternatively, wetting agents or other adjuvants are added. When diluted in water, the active ingredient dissolves. This gives a formulation with 10 wt .-% active ingredient content.
B Dispergierbare Konzentrate B Dispersible concentrates
20 Gew.-Teile Wirkstoff werden in 70 Gew.-Teilen Cyclohexanon unter Zusatz von 10 Gew.-Teilen eines Dispergiermittels z.B. Polyvinylpyrrolidon gelöst. Bei Verdünnung in Wasser ergibt sich eine Dispersion. Der Wirkstoffgehalt beträgt 20 Gew.-%20 parts by weight of active compound are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant, e.g. Polyvinylpyrrolidone dissolved. Dilution in water gives a dispersion. The active ingredient content is 20% by weight
C Emulgierbare Konzentrate C Emulsifiable concentrates
15 Gew.-Teile Wirkstoff werden in 75 Gew.-Teilen eines organisches Lösungsmittels (z.B. Alkylaromaten)-unter Zusatz von Ca-Dodecylbenzolsulfonat und Ricinusölethoxy- lat (jeweils 5 Gew.-Teile) gelöst. Bei der Verdünnung in Wasser ergibt sich eine Emulsion. Die Formulierung hat 15 Gew.-% Wirkstoffgehalt.15 parts by weight of active compound are dissolved in 75 parts by weight of an organic solvent (for example alkylaromatics) with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water results in an emulsion. The formulation has 15% by weight active ingredient content.
D Emulsionen D emulsions
25 Gew.-Teile Wirkstoff werden in 35 Gew.-Teilen eines organisches Lösungsmittels (z.B. Alkylaromaten) unter Zusatz von Ca-Dodecylbenzolsulfonat und Ricinusölethoxy- lat (jeweils 5 Gew.-Teile) gelöst. Diese Mischung wird mittels einer Emulgiermaschine (z.B. Ultraturax) in 30 Gew.Teile Wasser gegeben und zu einer homogenen Emulsion gebracht. Bei der Verdünnung in Wasser ergibt sich eine Emulsion. Die Formulierung hat einen Wirkstoffgehalt von 25 Gew.-%.25 parts by weight of active compound are dissolved in 35 parts by weight of an organic solvent (for example alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is added by means of an emulsifying machine (eg Ultraturax) in 30 parts by weight of water and a homogeneous emulsion brought. Dilution in water results in an emulsion. The formulation has an active ingredient content of 25% by weight.
E Suspensionen E suspensions
20 Gew.-Teile Wirkstoff werden unter Zusatz von 10 Gew.-Teilen Dispergier- und Netzmitteln und 70 Gew.-Teilen Wasser oder einem organischen Lösungsmittel in einer Rührwerkskugelmühle zu einer feinen Wirkstoffsuspension zerkleinert. Bei der Verdünnung in Wasser ergibt sich eine stabile Suspension des Wirkstoffs. Der Wirkstoffgehalt in der Formulierung beträgt 20 Gew.-% . 20 parts by weight of active compound are comminuted with the addition of 10 parts by weight dispersing and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine active substance suspension. Dilution in water results in a stable suspension of the active ingredient. The active ingredient content in the formulation is 20% by weight.
F Wasserdispergierbare und wasserlösliche Granulate F Water-dispersible and water-soluble granules
50 Gew.-Teile Wirkstoff werden unter Zusatz von 50 Gew-Teilen Dispergier- und Netzmitteln fein gemahlen und mittels technischer Geräte (z.B. Extrusion, Sprühturm, Wirbelschicht) als wasserdispergierbare oder wasserlösliche Granulate hergestellt. Bei der Verdünnung in Wasser ergibt sich eine stabile Dispersion oder Lösung des Wirkstoffs. Die Formulierung hat einen Wirkstoffgehalt von 50 Gew.-%.50 parts by weight of active compound are finely ground with the addition of 50 parts by weight of dispersants and wetting agents and prepared by means of industrial equipment (for example extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient. The formulation has an active ingredient content of 50% by weight.
G Wasserdispergierbare und wasserlösliche Pulver G Water-dispersible and water-soluble powders
75 Gew.-Teile Wirkstoff werden unter Zusatz von 25 Gew.-Teilen Dispergier- und Netzmitteln sowie Kieselsäuregel in einer Rotor-Strator Mühle vermählen. Bei der Verdünnung in Wasser ergibt sich eine stabile Dispersion oder Lösung des Wirkstoffs. Der Wirkstoffgehalt der Formulierung beträgt 75 Gew.-%. 75 parts by weight of active compound are ground with the addition of 25 parts by weight of dispersing and wetting agents and silica gel in a rotor-Strator mill. Dilution in water results in a stable dispersion or solution of the active ingredient. The active ingredient content of the formulation is 75% by weight.
H Gelformulierungen H gel formulations
In einer Kugelmühle werden 20 Gew.-Teile Wirkstoff, 10 Gew.-Teile Dispergiermittel, 1 Gew.-Teil Geliermittel und 70 Gew.-Teile Wasser oder eines organischen Lösungsmittels zu einer feinen Suspension vermählen. Bei der Verdünnung mit Wasser ergibt sich eine stabile Suspension mit 20 Gew.-% Wirkstoffgehalt. In a ball mill, 20 parts by weight of the active ingredient, 10 parts by weight of the dispersant, 1 part by weight of the gelling agent and 70 parts by weight of water or an organic solvent are ground to a fine suspension. Dilution with water results in a stable suspension with 20% by weight active ingredient content.
2. Produkte für die Direktapplikation2. Products for direct application
I Stäube I dusts
5 Gew.-Teile Wirkstoff werden fein gemahlen und mit 95 Gew.-Teilen feinteiligem Kaolin innig vermischt. Man erhält dadurch ein Stäubemittel mit 5 Gew.-% Wirkstoffgehalt. J Granulate (GR, FG, GG, MG) 5 parts by weight of active compound are finely ground and intimately mixed with 95 parts by weight of finely divided kaolin. This gives a dust with 5 wt .-% active ingredient content. J Granules (GR, FG, GG, MG)
0,5 Gew-Teile Wirkstoff werden fein gemahlen und mit 99,5 Gewichtsteilen Trägerstoffe verbunden. Gängige Verfahren sind dabei die Extrusion, die Sprühtrocknung oder die Wirbelschicht. Man erhält dadurch ein Granulat für die Direktapplikation mit 0,5 Gew.-% Wirkstoffgehalt. 0.5 parts by weight of active compound are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with 0.5 wt .-% active ingredient content.
K ULV- Lösungen (UL) K ULV solutions (UL)
10 Gew.-Teile Wirkstoff werden in 90 Gew.-Teilen eines organischen Lösungsmittels z.B. Xylol gelöst. Dadurch erhält man ein Produkt für die Direktapplikation mit 10 Gew.- % Wirkstoffgehalt. Die Applikation der Benzoylpyrazole der Formel I oder der sie enthaltenden herbizi- den Mittel kann im Vorauflauf-, im Nachauflaufverfahren oder zusammen mit dem Saatgut einer Kulturpflanze erfolgen. Es besteht auch die Möglichkeit, die herbiziden Mittel bzw. Wirkstoffe dadurch zu applizieren, dass mit den herbiziden Mitteln bzw. Wirkstoffen vorbehandeltes Saatgut einer Kulturpflanze ausgebracht wird. Sind die Wirkstoffe für gewisse Kulturpflanzen weniger verträglich, so können Ausbringungstechniken angewandt werden, bei welchen die herbiziden Mittel mit Hilfe der Spritzge- räte so gespritzt werden, dass die Blätter der empfindlichen Kulturpflanzen nach Möglichkeit nicht getroffen werden, während die Wirkstoffe auf die Blätter darunter wachsender unerwünschter Pflanzen oder die unbedeckte Bodenfläche gelangen (post- directed, lay-by). In einer weiteren Ausführungsform kann die Applikation der Benzoylpyrazole der Formel I oder der erfindungsgemäßen Mischungen bzw. der herbiziden Mittel durch Behandlung von Saatgut erfolgen.10 parts by weight of active compound are dissolved in 90 parts by weight of an organic solvent such as xylene. This gives a product for direct application with 10% by weight of active ingredient content. The application of the benzoylpyrazoles of the formula I or the herbicidal compositions containing them can be carried out in preemergence, postemergence or together with the seed of a crop. There is also the possibility of the herbicides Apply agents or active ingredients characterized in that with the herbicidal agents or active ingredients pretreated seed of a crop plant is applied. If the active substances are less compatible with certain crops, application techniques may be used in which the herbicidal agents are sprayed with the aid of the sprayers so that the leaves of the sensitive crops are not struck if possible, while the active ingredients on the leaves below grow unwanted plants or the uncovered soil surface (post-directed, lay-by). In a further embodiment, the application of the benzoylpyrazoles of the formula I or the mixtures according to the invention or the herbicidal agents can be carried out by treating seed.
Die Behandlung von Saatgut umfasst im Wesentlichen alle dem Fachmann geläufigen Techniken (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping, und seed pelleting) basierend auf den erfindungsgemäßen Benzoylpyrazolen der Formel I oder den erfindungsgemäßen Mischungen bzw. daraus hergestellten Mitteln. Hierbei können die herbiziden Mittel verdünnt oder unverdünnt aufgetragen werden. The treatment of seed comprises essentially all techniques familiar to the skilled worker (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed pelleting and seed pelleting) based on the benzoylpyrazoles of the formula according to the invention I or the mixtures according to the invention or agents produced therefrom. Here, the herbicidal agents can be diluted or applied undiluted.
Der Begriff Saatgut umfasst Saatgut aller Arten, wie z.B. Körner, Samen, Früchte, Knollen, Stecklinge und ähnliche Formen. Bevorzugt beschreibt der Begriff Saatgut hier Körner und Samen. The term seed includes seeds of all kinds, e.g. Grains, seeds, fruits, tubers, cuttings and similar forms. The term seed preferably describes grains and seeds here.
Als Saatgut kann Saatgut der oben erwähnten Nutzpflanzen aber auch das Saatgut transgener oder durch herkömmliche Züchtungsmethoden erhaltener Pflanzen eingesetzt werden. Seeds of the abovementioned crops but also the seeds of transgenic or obtained by conventional breeding methods plants can be used as seeds.
Die Aufwandmengen an Wirkstoff betragen je nach Bekämpfungsziel, Jahreszeit, Zielpflanzen und Wachstumsstadium 0.001 bis 3.0, vorzugsweise 0.01 bis 1.0 kg/ha aktive Substanz (a. S.). Zur Saatgutbehandlung werden die Benzoylpyrazole der Formel I üblicherweise in Mengen von 0,001 bis 10 kg pro 100 kg Saatgut eingesetzt.Depending on the control target, season, target plants and growth stage, the application rates of active ingredient are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a. S.). For seed treatment, the benzoylpyrazoles of the formula I are usually used in amounts of 0.001 to 10 kg per 100 kg of seed.
Im Folgenden wird die Herstellung von Benzoylpyrazolen der Formel I anhand von Beispielen erläutert ohne dabei den Gegenstand der vorliegenden Erfindung auf die gezeigten Beispiele zu begrenzen.In the following, the preparation of benzoylpyrazoles of the formula I is explained by way of examples without limiting the subject matter of the present invention to the examples shown.
Synthesebeispielesynthesis Examples
Die in den nachstehenden Synthesebeispielen wiedergegebenen Vorschriften wurden unter entsprechender Abwandlung der Ausgangsverbindungen zur Gewinnung weiterer Benzoylpyrazole der Formel I benutzt. Beispiel 1 : Herstellung von (1 -Ethyl-5-prop-2-ynyloxy-1 H-pyrazol-4-yl)-[4-methan- sulfonyl-2-methyl-3-(3-methyl-4,5-dihydro-isoxazol-5-yl)-phenyl]-methanonThe instructions given in the synthesis examples below were used with appropriate modification of the starting compounds to obtain further benzoylpyrazoles of the formula I. Example 1 Preparation of (1-ethyl-5-prop-2-ynyloxy-1H-pyrazol-4-yl) [4-methanesulfonyl-2-methyl-3- (3-methyl-4,5-) dihydro-isoxazol-5-yl) -phenyl] -methanone
Figure imgf000083_0001
Figure imgf000083_0001
1 .1 : 4-Methansulfonyl-2-methyl-3-(3-methyl-4,5-dihydro-isoxazol-5-yl)-benzoesäure- Chlorid
Figure imgf000083_0002
1: 1: 4-Methanesulfonyl-2-methyl-3- (3-methyl-4,5-dihydro-isoxazol-5-yl) -benzoic acid chloride
Figure imgf000083_0002
4-Methansulfonyl-2-methyl-3-(3-methyl-4,5-dihydro-isoxazol-5-yl)-benzoesäure (14,5 g, 48,8 mmol) wurde in Toluol (trocken, 160 ml_) unter Stickstoff vorgelegt. DMF (0,10 ml_) wurde zugegeben, und dann wurde Thionylchlorid (7,5 g, 63,4 mmol) zugetropft. Anschließend wurde 1 ,5 Stunden unter Rückfluss bei (120°C) gerührt. Die Reaktionsmischung wurde eingeengt, und das Rohprodukt (15,0 g) wurde ohne weitere Aufreinigung weiter umgesetzt. 4-Methanesulfonyl-2-methyl-3- (3-methyl-4,5-dihydro-isoxazol-5-yl) -benzoic acid (14.5 g, 48.8 mmol) was dissolved in toluene (dry, 160 mL) Nitrogen submitted. DMF (0.10 mL) was added and then thionyl chloride (7.5 g, 63.4 mmol) was added dropwise. It was then stirred for 1.5 hours under reflux at (120 ° C). The reaction mixture was concentrated and the crude product (15.0 g) was reacted further without further purification.
1 .2: 4-Methansulfonyl-2-methyl-3-(3-methyl-4,5-dihydro-isoxazol-5-yl)-benzoesäure 2- ethyl-2 H-pyrazol-3-yl-ester
Figure imgf000083_0003
1: 2: 4-Methanesulfonyl-2-methyl-3- (3-methyl-4,5-dihydro-isoxazol-5-yl) -benzoic acid 2-ethyl-2H-pyrazol-3-yl-ester
Figure imgf000083_0003
4-Methansulfonyl-2-methyl-3-(3-methyl-4,5-dihydro-isoxazol-5-yl)-benzoesäurechlorid (15,0 g, 47,5 mmol) wurde in Ethylenglykoldimethylether (DME) (125 ml_) vorgelegt. Kaliumcarbonat (8,2 g, 59,6 mmol) wurde zugegeben, und es wurde auf 0-5°C abgekühlt. Eine Lösung von 2-Ethyl-4-methyl-2H-pyrazol-3-ol (5,57 g, 49,7 mmol) in DME (125 ml_) wurde bei 0-5°C zugetropft. Die Kühlung wurde entfernt, und es wurde bei Raumtemperatur eine Stunde nachgerührt. Anschließend wurde nochmals Kaliumcarbonat (8,2 g, 59,6 mmol) zugegeben, und 24 Stunden lang unter Rückfluss erhitzt. Das Reaktionsgemisch wurde danach in Wasser eingerührt und dreimal mit Dichlormethan extrahiert. Die organische Phase wurde abgetrennt, über Natriumsulfat getrocknet, abfiltriert und unter Vakuum eingeengt. Das so erhaltene Rohprodukt (6,0 g) wurde ohne weitere Aufreinigung im nächsten Ansatz eingesetzt. 4-Methanesulfonyl-2-methyl-3- (3-methyl-4,5-dihydro-isoxazol-5-yl) -benzoic acid chloride (15.0 g, 47.5 mmol) was dissolved in ethylene glycol dimethyl ether (DME) (125 mL). submitted. Potassium carbonate (8.2 g, 59.6 mmol) was added and it was cooled to 0-5 ° C. A solution of 2-ethyl-4-methyl-2H-pyrazol-3-ol (5.57 g, 49.7 mmol) in DME (125 mL) was added dropwise at 0-5 ° C. The cooling was removed and stirring was continued at room temperature for one hour. Then potassium carbonate (8.2 g, 59.6 mmol) was added again and heated at reflux for 24 hours. The reaction mixture was then stirred into water and extracted three times with dichloromethane. The organic phase was separated, dried over sodium sulfate, filtered off and concentrated in vacuo. The resulting crude product (6.0 g) was used without further purification in the next batch.
1 .3: (1 -Ethyl-5-hydroxy-1 H-pyrazol-4-yl)-[4-methansulfonyl-2-methyl-3-(3-methyl-4,5- dihydro-isoxazol-5-yl)-phenyl]-methanon
Figure imgf000084_0001
1 .3: (1-Ethyl-5-hydroxy-1H-pyrazol-4-yl) - [4-methanesulfonyl-2-methyl-3- (3-methyl-4,5-dihydro-isoxazol-5-yl ) phenyl] -methanone
Figure imgf000084_0001
4-Methansulfonyl-2-methyl-3-(3-methyl-4,5-dihydro-isoxazol-5-yl)-benzoesäure-2-ethy^ 2H-pyrazol-3-yl-ester (6,0 g, Rohprodukt aus 1.2) wurde in Dioxan (50 mL vorgelegt, und Kaliumcarbonat (28,0 g, 203 mmol) wurde zugegeben. Nun wurde 2 Stunden lang unter Rückfluss erhitzt. Danach wurde das Reaktionsgemsich in Wasser eingerührt und dreimal mit Dichlormethan extrahiert. Die organische Phase wurde abgetrennt, über Natriumsulfat getrocknet, abfiltriert und unter Vakuum eingeengt. Das so erhaltene Rohprodukt (6,5 g) wurde ohne weitere Aufreinigung im nächsten Ansatz eingesetzt. 4-Methanesulfonyl-2-methyl-3- (3-methyl-4,5-dihydro-isoxazol-5-yl) -benzoic acid 2-ethyl ^ 2H-pyrazol-3-yl-ester (6.0 g, crude product from 1.2) was initially charged in dioxane (50 mL) and potassium carbonate (28.0 g, 203 mmol) was added, then refluxed for 2 hours, then the reaction mixture was stirred into water and extracted three times with dichloromethane was separated, dried over sodium sulfate, filtered off and concentrated in vacuo The crude product thus obtained (6.5 g) was used without further purification in the next batch.
'H-NMR (CDCIS): 1 ,5 (t, 3H), 2,1 (s, 3H), 2,4 (s, 3H), 3,2 (m, 1 H), 3,3 (s, 3H), 3,4 (m, 1 H), 4,1 (q, 2H), 5,2 (br s, 1 H), 6,4 (t 1 H), 7,3 (s, 1 H), 7,5 (d, 1 H), 8,1 (d, 1 H).1 H (CDCIS): 1.5 (t, 3H), 2.1 (s, 3H), 2.4 (s, 3H), 3.2 (m, 1H), 3.3 (s , 3H), 3.4 (m, 1H), 4.1 (q, 2H), 5.2 (br s, 1H), 6.4 (t 1 H), 7.3 (s, 1 H), 7.5 (d, 1H), 8.1 (d, 1H).
1 .4: (1 -Ethyl-5-prop-2-ynyloxy-1 H-pyrazol-4-yl)-[4-methansulfonyl-2-methyl-3-(3- methyl-4,5-dihydro-isoxazol-5-yl)-phenyl]-methanon1: 4: (1-Ethyl-5-prop-2-ynyloxy-1H-pyrazol-4-yl) - [4-methanesulfonyl-2-methyl-3- (3-methyl-4,5-dihydro-isoxazole -5-yl) -phenyl] -methanone
Figure imgf000084_0002
Figure imgf000084_0002
(1 -Ethyl-5-hydroxy-1 H-pyrazol-4-yl)-[4-methansulfonyl-2-methyl-3-(3-methyl-4,5- dihydro-isoxazol-5-yl)-phenyl]-methanon (6,5 g, 16,6 mmol) wurde in DMF (150 mL) bei Raumtemperatur vorgelegt. Kaliumcarbonat (2,8 g, 19,9 mmol) wurde zugegeben, und es wurde kurz nachgerührt. Anschließend wurde Propargylbromid (80%-ig in Toluol, 2,2 mL, 19,9 mmol) zugegeben, und es wurde über Nacht bei Raumtemperatur weiter gerührt. Das Reaktionsgemisch wurde in Wasser (ca. 1500 mL) eingerührt, danach wurde mit 10%-iger HCl angesäuert, und dreimal mit Methyl-t-Butyl Ether (MTBE) extrahiert. Die organische Phase wurde abgetrennt, einmal mit Wasser gewaschen, über Natriumsulfat getrocknet, und unter Vakuum eingeengt. Das Rohprodukt (4,0 g) wurde chromatographisch an Kieselgel greinigt (Essigester: Cyclohexan / 1 :1 ). Man erhielt 2,7g Produkt (38% Ausbeute).(1-Ethyl-5-hydroxy-1H-pyrazol-4-yl) - [4-methanesulfonyl-2-methyl-3- (3-methyl-4,5-dihydro-isoxazol-5-yl) -phenyl] -methanone (6.5 g, 16.6 mmol) was initially charged in DMF (150 mL) at room temperature. Potassium carbonate (2.8 g, 19.9 mmol) was added and stirred briefly. Subsequently, propargyl bromide (80% in toluene, 2.2 mL, 19.9 mmol) was added and stirring was continued overnight at room temperature. The reaction mixture was stirred into water (about 1500 mL), then acidified with 10% HCl and extracted three times with methyl t-butyl ether (MTBE). The organic phase was separated, washed once with water, dried over sodium sulfate, and concentrated in vacuo. The crude product (4.0 g) was purified by chromatography on silica gel (ethyl acetate: cyclohexane / 1: 1). This gave 2.7 g of product (38% yield).
'H-NMR (CDCIS): 1 ,5 (t, 3H), 2,1 (s, 3H), 2,3 (s, 3H), 2,5 (s, 1 H), 3,2 (m, 1 H), 3,3 (s, 3H), 3,4 (m, 1 H), 4,2 (q, 2H), 5,3 (s, 2H), 6,5 (t 1 H), 7,2 (s, 1 H), 7,4 (d, 1 H), 8,1 (d, 1 H). 1 H (CDCIS): 1.5 (t, 3H), 2.1 (s, 3H), 2.3 (s, 3H), 2.5 (s, 1H), 3.2 (m , 1H), 3.3 (s, 3H), 3.4 (m, 1H), 4.2 (q, 2H), 5.3 (s, 2H), 6.5 (t 1 H) , 7.2 (s, 1H), 7.4 (d, 1H), 8.1 (d, 1H).
O R O— N Nr. R R2 R4 R5 * Smp. RT* m/zORO-N No. RR2 R4 R5 * mp RT* m / z
[°C] [min] (M+H) [° C] [min] (M + H)
2 CH3 CHs HC= CCH2 C3H5- 68-71 - -2 CH3 CHs HC = CCH2 C3 H 5 68-71 -
3 Cl CHs HC= CCH2 (CH3)2CH- Harz 3,14 464,13 Cl CHs HC = CCH2 (CH3 )2 CH resin 3.14 464.1
4 Cl CHs HC= CCH2 C2Hs- Harz 2,92 450,14 Cl CHs HC = CCH2 C2 Hs resin 2.92 450.1
5 CHsO CHs HC= CCH2 C2Hs- Harz 2,82 446,15 CHsO CHs HC = CCH2 C2 Hs resin 2.82 446.1
6 Cl CHs H3CC= CCH2 (CH3)2CH- 85-105 - -6 Cl CHs H3 CC = CCH2 (CH3 )2 CH-85-105 - -
7 CHs CHs H3CC= CCH2 C2Hs- Harz 3,05 444,27 CHs CHs H3 CC = CCH2 C2 Hs resin 3.05 444.2
8 CHs CHF2 HC= CCH2 C2Hs- 135-142 - -8 CHs CHF2 HC = CCH2 C2 Hs-135-142 - -
9 CHs CHF2 HC= CCH2 (CH3)2CH- Öl 3,46 480,19 CHs CHF2 HC = CCH2 (CH3 )2 CH- oil 3.46 480.1
10 CHs CHsO HC= CCH2 C2Hs- 154 - -10 CHs CHsO HC = CCH2 C2 Hs 154 - -
1 1 CHs CHsO HC= CCH2 (CH3)2CH- 75-80 - -1 1 CHs CHsO HC = CCH2 (CH3 )2 CH- 75-80 - -
* R5: C3H5- ist cyclopropyl;* R5 : C3H5- is cyclopropyl;
* RP-18 Säule (Chromolith Speed ROD von Merck KgaA, Deutschland), 50*4,6 mm; Eluent: Acetonitril + 0,1 % Trifluoressigsäure (TFA)/ Wasser + 0,1 % TFA, mit einem Gradienten von 5 : 95 bis 100 : 0 in 5 Minuten bei 40°C, Fluss-rate 1 ,8 ml/min.* RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany), 50* 4.6 mm; Eluent: acetonitrile + 0.1% trifluoroacetic acid (TFA) / water + 0.1% TFA, with a gradient of 5:95 to 100: 0 in 5 minutes at 40 ° C, flow rate 1, 8 ml / min.
Anwendungsbeispieleapplications
Die herbizide Wirkung der erfindungsgemäßen Benzoylpyrazole der Formel I und Mischungen der Formel I ließ sich durch Gewächshausversuche zeigen: The herbicidal action of the inventive benzoylpyrazoles of the formula I and mixtures of the formula I was demonstrated by greenhouse experiments:
Als Kulturgefäße dienten Plastiktöpfe mit lehmigem Sand mit etwa 3%-5% Humus als Substrat. Die Samen der Testpflanzen wurden nach Arten getrennt eingesät.The culture vessels used were plastic pots with loamy sand with about 3% -5% humus as substrate. The seeds of the test plants were sown separately by species.
Bei Vorauflaufbehandlung wurden die in Wasser suspendierten oder emulgierten Wirkstoffe direkt nach Einsaat mittels fein verteilender Düsen aufgebracht. Die Gefäße wurden leicht beregnet, um Keimung und Wachstum zu fördern, und anschließend mit durchsichtigen Plastikhauben abgedeckt, bis die Pflanzen angewachsen waren. Diese Abdeckung bewirkt ein gleichmäßiges Keimen der Testpflanzen, sofern dies nicht durch die Wirkstoffe beeinträchtigt wurde. In pre-emergence treatment, the active ingredients suspended or emulsified in water were applied directly after sowing by means of finely distributing nozzles. The jars were lightly rained to promote germination and growth and then covered with clear plastic hoods until the plants had grown. This cover causes a uniform germination of the test plants, if it was not affected by the active ingredients.
Zum Zweck der Nachauflaufbehandlung wurden die Testpflanzen je nach Wuchsform erst bis zu einer Wuchshöhe von 3 bis 15 cm angezogen und dann mit den in Wasser suspendierten oder emulgierten Wirkstoffen behandelt. Die Testpflanzen wurden dafür entweder direkt gesät und in den gleichen Gefäßen aufgezogen oder sie wurden erst als Keimpflanzen getrennt angezogen und einige Tage vor der Behand- lung in die Versuchsgefäße verpflanzt. For the postemergence treatment, the test plants were grown depending on the growth form only to a height of from 3 to 15 cm and then treated with the suspended or emulsified in water agents. For this purpose, the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
Die Pflanzen wurden artenspezifisch bei Temperaturen von 10 - 25°C bzw. 20 - 35°C gehalten. Die Versuchsperiode erstreckte sich über 2 bis 4 Wochen. Während dieser Zeit wurden die Pflanzen gepflegt, und ihre Reaktion auf die einzelnen Behandlungen wurde ausgewertet.The plants were kept species-specific at temperatures of 10 - 25 ° C and 20 - 35 ° C, respectively. The trial period lasted for 2 to 4 weeks. During this Time the plants were cared for, and their response to each treatment was evaluated.
Bewertet wurde nach einer Skala von 0 bis 100. Dabei bedeutet 100 kein Aufgang der Pflanzen bzw. völlige Zerstörung zumindest der oberirdischen Teile und 0 keine Schädigung oder normaler Wachstumsverlauf. Eine gute herbizide Aktivität ist bei Werten von wenigstens 70 und eine sehr gute herbizide Aktivität ist bei Werten von wenigstens 85 gegeben. The rating was based on a scale of 0 to 100. 100 means no emergence of the plants or complete destruction of at least the above-ground parts and 0 no damage or normal growth course. A good herbicidal activity is at values of at least 70 and a very good herbicidal activity is given at values of at least 85.
Die in den Gewächshausversuchen verwendeten Pflanzen setzten sich aus folgen- den Arten zusammen:The plants used in the greenhouse experiments are composed of the following species:
Figure imgf000086_0002
Figure imgf000086_0002
Figure imgf000086_0001
Figure imgf000086_0001
Nr. R R2 R4 R5 *No. RR2 R4 R5 *
1 CH3 CHs HC= CCH2 C2H5-
Figure imgf000087_0001
1 CH3 CHs HC = CCH2 C2 H 5 -
Figure imgf000087_0001
* R5: C3H5- ist cyclopropyl;* R5 : C3H5- is cyclopropyl;
Nr. 1 2 3 4 5 6 7 8 9 10 1 1No. 1 2 3 4 5 6 7 8 9 10 1 1
[g/ha] 125 125 62.5 62.5 62.5 62.5 62.5 62.5 62.5 125 125[g / ha] 125 125 62.5 62.5 62.5 62.5 62.5 62.5 62.5 125 125
Schädigung in [%] Injury in [%]
CHEAL 100 100 100 100 100 100 100 100 100 98 98 CHEAL 100 100 100 100 100 100 100 100 100 98 98
SETFA 100 100 100 100 95 100 98 98 100 98 98SETFA 100 100 100 100 95 100 98 98 100 98 98
ECHCG 100 100 100 100 100 100 95 100 98 98 98ECHCG 100 100 100 100 100 100 95 100 98 98 98

Claims

Patentansprüche:claims:
1 . Herbizide Mischung umfassend1 . Comprising herbicidal mixture
a) als Komponente A eine herbizid wirksame Menge eines Benzoylpyrazols der Formel I , a) as component A, a herbicidally effective amount of a benzoylpyrazole of the formula I,
Figure imgf000088_0001
Figure imgf000088_0001
worin die Variablen folgende Bedeutungen haben: wherein the variables have the following meanings:
R1 Halogen, Ci-C4-Alkyl, Ci-C4-Alkoxy;R1 is halogen, C1 -C4 -alkyl, C 1 -C4 -alkoxy;
R2 Ci-C -Alkyl, Ci-C -Halogenalkyl, Ci-C4-Alkoxy;R2 is C 1 -C4 -alkyl, C 1 -C4 -haloalkyl, C 1 -C4 -alkoxy;
R3 Ci-C -Alkylsulfonyl;R3 is C 1 -C 4 alkylsulfonyl;
R4 Wasserstoff, C3-C6-Alkinyl, C3-C6-Halogenalkinyl;R4 is hydrogen, C3 -C6 -alkynyl, C3 -C6 -haloalkynyl;
R5 C2-C4-Alkyl, C3-C4-Cycloalkyl;R5 is C2 -C4 -alkyl, C3 -C4 -cycloalkyl;
R6 Wasserstoff, Ci-C4-Alkyl;R6 is hydrogen, C 1 -C4 -alkyl;
oder dessen landwirtschaftlich geeigneten Salzes; or its agriculturally suitable salt;
und and
b) als Komponente B eine antidotisch wirksame Menge eines Safeners. b) as component B, an antidote effective amount of a safener.
Herbizide Mischung gemäß Anspruch 1 , wobei die Komponente B ausgewählt ist aus den Safenerklassen der (Chinolin-8-oxy)essigsäuren, 1 -Phenyl-5-haloalkyl-1 H- 1 ,2,4-triazol-3-carbonsäuren, 1 -Phenyl-4,5-dihydro-5-alkyl-1 H-pyrazol-3,5- dicarbonsäuren, 4,5-Dihydro-5,5-diaryl-3-isoxazolcarbonsäuren, Dichloroacetamide, alpha-Oximinophenylacetonitrile, Acetophenonoxime, 4,6-Dihalo-2- phenylpyrimidine, N-[[4-(Aminocarbonyl)phenyl]sulfonyl]-2-benzoesäureamide, 1 ,8- Naphthalsäureanhydrid, 2-Halo-4-(haloalkyl)-5-thiazolcarbonsäuren, Phosphorthio- late, N-Alkyl-O-phenylcarbamate und 2-Oxo-nicotinsäureamide sowie deren landwirtschaftlich geeigneten Salze, und vorausgesetzt sie haben eine Säurefunktion, deren landwirtschaftlich geeigneten Derivate, wie Amide, Ester und Thioester.A herbicidal mixture according to claim 1, wherein component B is selected from safener classes of (quinoline-8-oxy) acetic acids, 1-phenyl-5-haloalkyl-1 H-1, 2,4-triazole-3-carboxylic acids, 1 - Phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenone oximes, 4,6 Dihalo-2-phenylpyrimidines, N - [[4- (aminocarbonyl) phenyl] sulfonyl] -2-benzoic acid amides, 1,8-naphthalic anhydride, 2-halo-4- (haloalkyl) -5-thiazolecarboxylic acids, phosphorothioate, N Alkyl-O-phenylcarbamate and 2-oxo-nicotinic acid amides and their agriculturally suitable salts, and provided they have an acid function, their agriculturally suitable derivatives, such as amides, esters and thioesters.
Herbizide Mischung gemäß Anspruch 1 , wobei die Komponente B ausgewählt ist aus der Gruppe der Safener Benoxacor, Cloquintocet, Cyometrinil, Cyprosulfamid, Dichlormid, Dicyclonon, Dietholat, Fenchlorazol, Fenclorim, Flurazol, Fluxofenim, Furilazol, Isoxadifen, Mefenpyr, Mephenat, Naphthalinsäureanhydrid, Oxabetrinil.A herbicidal mixture according to claim 1, wherein component B is selected from the group of safeners Benoxacor, Cloquintocet, Cyometrinil, Cyprosulfamide, Dichlormid, Dicyclonon, Dietholate, Fenchlorazole, Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen, Mefenpyr, Mephenate, Naphthalic Anhydride, Oxabetrinil ,
Herbizide Mischung gemäß einem der Ansprüche 1 bis 3, wobei die Komponente A ein Benzoylpyrazol der Formel I ist, worin die Variablen folgende Bedeutungen haben:A herbicidal mixture according to any one of claims 1 to 3, wherein the component A is a benzoylpyrazole of the formula I in which the variables have the following meanings:
R1 Ci-C4-Alkyl;R1 is C1 -C4 -alkyl;
R2 Ci-C4-Alkyl; R3 Ci-C4-Alkylsulfonyl;R2 is C 1 -C4 -alkyl; R3 is C 1 -C4 -alkylsulfonyl;
R4 Wasserstoff, C3-C6-Alkinyl;R4 is hydrogen, C3 -C6 -alkynyl;
R5 Ethyl, Propan-2-yl, Cyclopropyl;R5 is ethyl, propan-2-yl, cyclopropyl;
R6 Wasserstoff; oder dessen landwirtschaftlich geeignetes Salz.
Figure imgf000089_0001
Herbizide Mischung gemäß einem der Ansprüche 1 bis 3, wobei die Komponente A ein Benzoylpyrazol der Formel I ist, worin die Variablen folgende Bedeutungen haben:R6 is hydrogen; or its agriculturally suitable salt.
Figure imgf000089_0001
A herbicidal mixture according to any one of claims 1 to 3, wherein the component A is a benzoylpyrazole of the formula I in which the variables have the following meanings:
R1 Methyl;R1 is methyl;
R2 Methyl;R2 is methyl;
R3 Methylsulfonyl;R3 is methylsulfonyl;
R4 Wasserstoff, Prop-2-inyl;R4 is hydrogen, prop-2-ynyl;
R5 Ethyl, Propan-2-yl, Cyclopropyl;R5 is ethyl, propan-2-yl, cyclopropyl;
R6 Wasserstoff; oder dessen landwirtschaftlich geeignetes Salz.
Figure imgf000089_0002
Benzoylpyrazole der Formel I,R6 is hydrogen; or its agriculturally suitable salt.
Figure imgf000089_0002
Benzoylpyrazoles of the formula I,
Figure imgf000089_0003
Figure imgf000089_0003
worin die Variablen folgende Bedeutungen haben: wherein the variables have the following meanings:
R1 Halogen, Ci-C4-Alkyl, Ci-C4-Alkoxy;R1 is halogen, C1 -C4 -alkyl, C 1 -C4 -alkoxy;
R2 d-C4-Alkyl, Ci-C4-Halogenalkyl, Ci-C4-Alkoxy;R2 dC4 alkyl,Ci-C4-haloalkyl, Ci-C4 alkoxy;
R3 Ci-C4-Alkylsulfonyl;R3 is C 1 -C4 -alkylsulfonyl;
R4 Cs-Ce-Alkinyl, C3-C6-Halogenalkinyl;R4 is Cs-Ce-alkynyl, C3 -C6 -haloalkynyl;
R5 C2-C4-Alkyl, C3-C4-Cycloalkyl;R5 is C2 -C4 -alkyl, C3 -C4 -cycloalkyl;
R6 Wasserstoff, Ci-C4-Alkyl.
Figure imgf000089_0004
Benzoylpyrazole der Formel I gemäß Anspruch 6, worinR6 is hydrogen, C 1 -C4 -alkyl.
Figure imgf000089_0004
Benzoylpyrazoles of the formula I according to claim 6, wherein
R1 d-C4-Alkyl;R1 is dC4 alkyl;
R2 d-C4-Alkyl;R2 is dC4 alkyl;
R3 Ci-C4-Alkylsulfonyl;R3 is C 1 -C4 -alkylsulfonyl;
R4 Cs-Ce-Alkinyl;R4 is Cs-Ce-alkynyl;
R5 Ethyl, Propan-2-yl, Cyclopropyl;R5 is ethyl, propan-2-yl, cyclopropyl;
R6 Wasserstoff; bedeutet.R6 is hydrogen; means.
Benzoylpyrazole der Formel I gemäß Anspruch 6 oder 7,Benzoylpyrazoles of the formula I according to Claim 6 or 7,
Figure imgf000089_0005
R1 Ci-C2-Alkyl;
Figure imgf000089_0005
R1 is C1 -C2 -alkyl;
R2 Ci-C2-Alkyl;R2 is C1 -C2 -alkyl;
R3 Ci-C2-Alkylsulfonyl;R3 is C1 -C2 -alkylsulfonyl;
R4 Cs-Ce-Alkinyl; R5 Ethyl, Propan-2-yl, Cyclopropyl;R4 is Cs-Ce-alkynyl; R5 is ethyl, propan-2-yl, cyclopropyl;
R6 Wasserstoff; bedeutet.R6 is hydrogen; means.
9. Benzoylpyrazole der Formel I gemäß einem der Ansprüche 6 bis 8, worin9. Benzoylpyrazoles of the formula I according to any one of claims 6 to 8, wherein
R1 Methyl;R1 is methyl;
R2 Methyl;R2 is methyl;
R3 Methylsulfonyl;R3 is methylsulfonyl;
R4 Prop-2-inyl;R4 is prop-2-ynyl;
R5 Ethyl, Propan-2-yl, Cyclopropyl;R5 is ethyl, propan-2-yl, cyclopropyl;
R6 Wasserstoff; bedeutet.R6 is hydrogen; means.
10. Verfahren zur Herstellung von Benzoylpyrazolen der Formel I gemäß Anspruch 6, dadurch gekennzeichnet, dass Formel II,10. Process for the preparation of benzoylpyrazoles of the formula I according to claim 6, characterized in that formula II,
Figure imgf000090_0001
Figure imgf000090_0001
wobei die Variablen R5 und R6 die unter Anspruch 6 genannten Bedeutungen hawhere the variables R5 and R6 have the meanings mentioned under claim 6 ha
Figure imgf000090_0002
Figure imgf000090_0002
wobei die Variablen R1 bis R3 die unter Anspruch 6 genannten Bedeutungen haben und L1 für eine nucleophil verdrängbare Abgangsgruppe steht, acyliert und das Acy- lierungsprodukt, gegebenenfalls in Gegenwart eines Katalysators, zu den Benzoylpyrazolen der Formel I (mit R4 = H) umlagert und zur Herstellung von Benzoylpyrazolen der Formel I (mit R4 H) mit einer Verbindung der Formel V,wherein the variables R1 to R3 have the meanings mentioned under claim 6 and L1 is a nucleophilically displaceable leaving group acylated and the acylation lierungsprodukt, optionally in the presence of a catalyst, to the benzoylpyrazoles of formula I (with R4 = H ) and for the preparation of Benzoylpyrazolen of the formula I (with R4 H) with a compound of the formula V,
L2-R4 VL2 -R4 V
wobei R4 die unter Anspruch 6 genannte Bedeutung hat und L2 für eine nucleophil verdrängbare Abgangsgruppe steht, umsetzt.wherein R4 has the meaning given in claim 6 and L2 is a nucleophilically displaceable leaving group, is reacted.
1 1 . Mittel, enthaltend eine herbizide Mischung nach einem der Ansprüche 1 bis 5 oder eine herbizid wirksame Menge eines Benzoylpyrazols der Formel I nach einem der Ansprüche 6 bis 9 und für die Formulierung von Pflanzenschutzmitteln übliche Hilfsmittel.1 1. Agent comprising a herbicidal mixture according to one of claims 1 to 5 or a herbicidally effective amount of a benzoylpyrazole of the formula I according to any one of claims 6 to 9 and auxiliaries customary for the formulation of crop protection agents.
12. Mittel gemäß Anspruch 1 1 , enthaltend mindestens ein weiteres Herbizid.12. Composition according to claim 1 1, containing at least one further herbicide.
13. Mittel gemäß Anspruch 1 1 , enthaltend mindestens zwei weitere Herbizide.13. Composition according to claim 1 1, containing at least two further herbicides.
14. Verfahren zur Bekämpfung unerwünschten Pflanzenwuchses, dadurch gekennzeichnet, dass man eine herbizide Mischung nach einem der Ansprüche 1 bis 5 o- der eine herbizid wirksame Menge eines Benzoylpyrazols der Formel I nach einem der Ansprüche 6 bis 9 auf Pflanzen, deren Samen und/oder deren Lebensraum einwirken lässt.14. A method for controlling undesired plant growth, characterized in that a herbicidal mixture according to any one of claims 1 to 5 o- a herbicidally effective amount of a Benzoylpyrazols of formula I according to any one of claims 6 to 9 on plants whose seeds and / or whose habitat has an effect.
15. Verfahren gemäß Anspruch 14, dadurch gekennzeichnet, dass die Pflanze Mais oder Getreide, der Samen Mais- oder Getreidesaatgut und/oder der Lebensraum Mais- oder eine Getreideanbaufläche ist.15. The method according to claim 14, characterized in that the plant is maize or cereals, the seed maize or cereal seed and / or the habitat maize or a cereal cropping area.
PCT/EP2010/0683522009-12-012010-11-293- (4, 5 -dihydroisoxazol- 5 -yl) benzoylpyrazole compounds and mixtures thereof with safenersWO2011067184A1 (en)

Applications Claiming Priority (2)

Application NumberPriority DateFiling DateTitle
EP09177628.62009-12-01
EP091776282009-12-01

Publications (1)

Publication NumberPublication Date
WO2011067184A1true WO2011067184A1 (en)2011-06-09

Family

ID=43558034

Family Applications (1)

Application NumberTitlePriority DateFiling Date
PCT/EP2010/068352WO2011067184A1 (en)2009-12-012010-11-293- (4, 5 -dihydroisoxazol- 5 -yl) benzoylpyrazole compounds and mixtures thereof with safeners

Country Status (1)

CountryLink
WO (1)WO2011067184A1 (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication numberPriority datePublication dateAssigneeTitle
US8822377B2 (en)2011-02-112014-09-02Basf SeHerbicidal compositions comprising topramezone and pinoxaden
CN111285863A (en)*2018-12-072020-06-16青岛清原化合物有限公司4- (3-heterocyclyl-1-benzoyl) pyrazole compound or salt thereof, preparation method, herbicide composition and application
EP3829308A1 (en)*2018-07-312021-06-09Belchim Crop Protection NVSynergistically effective herbicide composition comprising pyridate and at least one defined 4-hppd inhibitor
RU2803120C2 (en)*2018-07-312023-09-06Белчим Кроп Протекшн НвSynergistically effective herbicide composition containing pyridate and mesotrione

Citations (41)

* Cited by examiner, † Cited by third party
Publication numberPriority datePublication dateAssigneeTitle
US4643757A (en)1985-05-201987-02-17Nissan Chemical Industries, Ltd.Herbicidal 4-benzoyl-1-methyl-5-hydroxypyrazoles
EP0240001A1 (en)1986-04-021987-10-07Nissan Chemical Industries Ltd.2-Pyrazolin-5-ones and a process for production thereof
EP0242236A1 (en)1986-03-111987-10-21Plant Genetic Systems N.V.Plant cells resistant to glutamine synthetase inhibitors, made by genetic engineering
EP0257993A2 (en)1986-08-261988-03-02E.I. Du Pont De Nemours And CompanyNucleic acid fragment encoding herbicide resistant plant acetolactate synthase
EP0282944A2 (en)1987-03-171988-09-21Nissan Chemical Industries Ltd.Pyrazole derivative and herbicide containing it
EP0374753A2 (en)1988-12-191990-06-27American Cyanamid CompanyInsecticidal toxines, genes coding therefor, antibodies binding them, transgenic plant cells and plants expressing these toxines
EP0392225A2 (en)1989-03-241990-10-17Ciba-Geigy AgDisease-resistant transgenic plants
US5013659A (en)1987-07-271991-05-07E. I. Du Pont De Nemours And CompanyNucleic acid fragment encoding herbicide resistant plant acetolactate synthase
EP0427529A1 (en)1989-11-071991-05-15Pioneer Hi-Bred International, Inc.Larvicidal lectins and plant insect resistance based thereon
EP0451878A1 (en)1985-01-181991-10-16Plant Genetic Systems, N.V.Modifying plants by genetic engineering to combat or control insects
WO1992000377A1 (en)1990-06-251992-01-09Monsanto CompanyGlyphosate tolerant plants
WO1993007278A1 (en)1991-10-041993-04-15Ciba-Geigy AgSynthetic dna sequence having enhanced insecticidal activity in maize
WO1995034656A1 (en)1994-06-101995-12-21Ciba-Geigy AgNovel bacillus thuringiensis genes coding toxins active against lepidopteran pests
WO1996026206A1 (en)1995-02-241996-08-29Basf AktiengesellschaftPyrazol-4-yl-benzoyl derivatives and their use as herbicides
WO1996026202A1 (en)1995-02-211996-08-29Degussa AktiengesellschaftProcess for producing thietanones
US5559024A (en)1988-03-231996-09-24Rhone-Poulenc AgrochimieChimeric nitrilase-encoding gene for herbicidal resistance
WO1997041118A1 (en)1996-04-261997-11-06Nippon Soda Co., Ltd.Benzene derivatives substituted by heterocycles and herbicides
WO1997041116A1 (en)1996-04-261997-11-06Nippon Soda Co., Ltd.Benzene derivatives substituted by heterocycles and herbicides
WO1997041218A1 (en)1996-04-291997-11-06Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical CollegeHerbicide resistant rice
WO1997041117A1 (en)1996-04-261997-11-06Nippon Soda Co., Ltd.Novel benzene derivatives substituted by heterocycles and herbicides
WO1998002526A1 (en)1996-07-171998-01-22Michigan State UniversityImidazolinone herbicide resistant sugar beet plants
WO1998002527A1 (en)1996-07-171998-01-22Michigan State UniversityImidazolinone herbicide resistant sugar beet plants
WO1998031682A1 (en)1997-01-171998-07-23Basf Aktiengesellschaft4-(3-heterocyclyl-1-benzoyl)pyrazoles and their use as herbicides
WO1998031681A1 (en)1997-01-171998-07-23Basf Aktiengesellschaft3-heterocyclyl-substituted benzoyl derivatives
WO1999058509A1 (en)1998-05-111999-11-18Basf AktiengesellschaftMethod for producing isoxazoline-3-yl-acyl benzene
WO1999066795A1 (en)1998-06-231999-12-29Aventis Cropscience GmbhCombination of herbicides and safeners
WO2000026390A2 (en)1998-10-292000-05-11American Cyanamid CompanyGenes and vectors for conferring herbicide resistance in plants
US6222100B1 (en)1984-03-062001-04-24Mgi Pharma, Inc.Herbicide resistance in plants
WO2001046182A1 (en)*1999-12-222001-06-28Basf Aktiengesellschaft3-(4,5-dihydroisoxazole-5-yl)benzoylpyrazole
WO2001082685A1 (en)2000-04-282001-11-08Basf AktiengesellschaftUse of the maize x112 mutant ahas 2 gene and imidazolinone herbicides for selection of transgenic monocots, maize, rice and wheat plants resistant to the imidazolinone herbicides
WO2001083459A2 (en)2000-05-042001-11-08Basf AktiengesellschaftUracil substituted phenyl sulfamoyl carboxamides
WO2002015701A2 (en)2000-08-252002-02-28Syngenta Participations AgBacillus thuringiensis crystal protein hybrids
WO2003014357A1 (en)2001-08-092003-02-20University Of SaskatchewanWheat plants having increased resistance to imidazolinone herbicides
WO2003013225A2 (en)2001-08-092003-02-20Northwest Plant Breeding CompanyWheat plants having increased resistance to imidazolinone herbicides
WO2003014356A1 (en)2001-08-092003-02-20University Of SaskatchewanWheat plants having increased resistance to imidazolinone herbicides
WO2003018810A2 (en)2001-08-312003-03-06Syngenta Participations AgModified cry3a toxins and nucleic acid sequences coding therefor
WO2003052073A2 (en)2001-12-172003-06-26Syngenta Participations AgNovel corn event
WO2004016073A2 (en)2002-07-102004-02-26The Department Of Agriculture, Western AustraliaWheat plants having increased resistance to imidazolinone herbicides
WO2004106529A2 (en)2003-05-282004-12-09Basf AktiengesellschaftWheat plants having increased tolerance to imidazolinone herbicides
WO2005020673A1 (en)2003-08-292005-03-10Instituto Nacional De Technologia AgropecuariaRice plants having increased tolerance to imidazolinone herbicides
WO2008074991A1 (en)2006-12-212008-06-26Syngenta LimitedNovel herbicides

Patent Citations (42)

* Cited by examiner, † Cited by third party
Publication numberPriority datePublication dateAssigneeTitle
US6222100B1 (en)1984-03-062001-04-24Mgi Pharma, Inc.Herbicide resistance in plants
EP0451878A1 (en)1985-01-181991-10-16Plant Genetic Systems, N.V.Modifying plants by genetic engineering to combat or control insects
US4643757A (en)1985-05-201987-02-17Nissan Chemical Industries, Ltd.Herbicidal 4-benzoyl-1-methyl-5-hydroxypyrazoles
EP0242236A1 (en)1986-03-111987-10-21Plant Genetic Systems N.V.Plant cells resistant to glutamine synthetase inhibitors, made by genetic engineering
EP0242246A1 (en)1986-03-111987-10-21Plant Genetic Systems N.V.Plant cells resistant to glutamine synthetase inhibitors, made by genetic engineering
EP0240001A1 (en)1986-04-021987-10-07Nissan Chemical Industries Ltd.2-Pyrazolin-5-ones and a process for production thereof
EP0257993A2 (en)1986-08-261988-03-02E.I. Du Pont De Nemours And CompanyNucleic acid fragment encoding herbicide resistant plant acetolactate synthase
EP0282944A2 (en)1987-03-171988-09-21Nissan Chemical Industries Ltd.Pyrazole derivative and herbicide containing it
US5013659A (en)1987-07-271991-05-07E. I. Du Pont De Nemours And CompanyNucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5559024A (en)1988-03-231996-09-24Rhone-Poulenc AgrochimieChimeric nitrilase-encoding gene for herbicidal resistance
EP0374753A2 (en)1988-12-191990-06-27American Cyanamid CompanyInsecticidal toxines, genes coding therefor, antibodies binding them, transgenic plant cells and plants expressing these toxines
EP0392225A2 (en)1989-03-241990-10-17Ciba-Geigy AgDisease-resistant transgenic plants
EP0427529A1 (en)1989-11-071991-05-15Pioneer Hi-Bred International, Inc.Larvicidal lectins and plant insect resistance based thereon
WO1992000377A1 (en)1990-06-251992-01-09Monsanto CompanyGlyphosate tolerant plants
WO1993007278A1 (en)1991-10-041993-04-15Ciba-Geigy AgSynthetic dna sequence having enhanced insecticidal activity in maize
WO1995034656A1 (en)1994-06-101995-12-21Ciba-Geigy AgNovel bacillus thuringiensis genes coding toxins active against lepidopteran pests
WO1996026202A1 (en)1995-02-211996-08-29Degussa AktiengesellschaftProcess for producing thietanones
WO1996026206A1 (en)1995-02-241996-08-29Basf AktiengesellschaftPyrazol-4-yl-benzoyl derivatives and their use as herbicides
WO1997041117A1 (en)1996-04-261997-11-06Nippon Soda Co., Ltd.Novel benzene derivatives substituted by heterocycles and herbicides
WO1997041116A1 (en)1996-04-261997-11-06Nippon Soda Co., Ltd.Benzene derivatives substituted by heterocycles and herbicides
WO1997041118A1 (en)1996-04-261997-11-06Nippon Soda Co., Ltd.Benzene derivatives substituted by heterocycles and herbicides
WO1997041218A1 (en)1996-04-291997-11-06Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical CollegeHerbicide resistant rice
WO1998002526A1 (en)1996-07-171998-01-22Michigan State UniversityImidazolinone herbicide resistant sugar beet plants
WO1998002527A1 (en)1996-07-171998-01-22Michigan State UniversityImidazolinone herbicide resistant sugar beet plants
WO1998031682A1 (en)1997-01-171998-07-23Basf Aktiengesellschaft4-(3-heterocyclyl-1-benzoyl)pyrazoles and their use as herbicides
WO1998031681A1 (en)1997-01-171998-07-23Basf Aktiengesellschaft3-heterocyclyl-substituted benzoyl derivatives
WO1999058509A1 (en)1998-05-111999-11-18Basf AktiengesellschaftMethod for producing isoxazoline-3-yl-acyl benzene
WO1999066795A1 (en)1998-06-231999-12-29Aventis Cropscience GmbhCombination of herbicides and safeners
WO2000026390A2 (en)1998-10-292000-05-11American Cyanamid CompanyGenes and vectors for conferring herbicide resistance in plants
WO2001046182A1 (en)*1999-12-222001-06-28Basf Aktiengesellschaft3-(4,5-dihydroisoxazole-5-yl)benzoylpyrazole
WO2001082685A1 (en)2000-04-282001-11-08Basf AktiengesellschaftUse of the maize x112 mutant ahas 2 gene and imidazolinone herbicides for selection of transgenic monocots, maize, rice and wheat plants resistant to the imidazolinone herbicides
WO2001083459A2 (en)2000-05-042001-11-08Basf AktiengesellschaftUracil substituted phenyl sulfamoyl carboxamides
WO2002015701A2 (en)2000-08-252002-02-28Syngenta Participations AgBacillus thuringiensis crystal protein hybrids
WO2003014357A1 (en)2001-08-092003-02-20University Of SaskatchewanWheat plants having increased resistance to imidazolinone herbicides
WO2003013225A2 (en)2001-08-092003-02-20Northwest Plant Breeding CompanyWheat plants having increased resistance to imidazolinone herbicides
WO2003014356A1 (en)2001-08-092003-02-20University Of SaskatchewanWheat plants having increased resistance to imidazolinone herbicides
WO2003018810A2 (en)2001-08-312003-03-06Syngenta Participations AgModified cry3a toxins and nucleic acid sequences coding therefor
WO2003052073A2 (en)2001-12-172003-06-26Syngenta Participations AgNovel corn event
WO2004016073A2 (en)2002-07-102004-02-26The Department Of Agriculture, Western AustraliaWheat plants having increased resistance to imidazolinone herbicides
WO2004106529A2 (en)2003-05-282004-12-09Basf AktiengesellschaftWheat plants having increased tolerance to imidazolinone herbicides
WO2005020673A1 (en)2003-08-292005-03-10Instituto Nacional De Technologia AgropecuariaRice plants having increased tolerance to imidazolinone herbicides
WO2008074991A1 (en)2006-12-212008-06-26Syngenta LimitedNovel herbicides

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
"Modern Crop Protection Compounds", vol. 1, 2007, WILEY VCH
B. HOCK; C. FEDTKE; R. R. SCHMIDT: "Herbizide", 1995, GEORG THIEME VERLAG
J. PRAKT. CHEM., vol. 315, 1973, pages 383

Cited By (5)

* Cited by examiner, † Cited by third party
Publication numberPriority datePublication dateAssigneeTitle
US8822377B2 (en)2011-02-112014-09-02Basf SeHerbicidal compositions comprising topramezone and pinoxaden
EP3829308A1 (en)*2018-07-312021-06-09Belchim Crop Protection NVSynergistically effective herbicide composition comprising pyridate and at least one defined 4-hppd inhibitor
RU2803120C2 (en)*2018-07-312023-09-06Белчим Кроп Протекшн НвSynergistically effective herbicide composition containing pyridate and mesotrione
CN111285863A (en)*2018-12-072020-06-16青岛清原化合物有限公司4- (3-heterocyclyl-1-benzoyl) pyrazole compound or salt thereof, preparation method, herbicide composition and application
CN111285863B (en)*2018-12-072022-04-26青岛清原化合物有限公司4- (3-heterocyclyl-1-benzoyl) pyrazole compound or salt thereof, preparation method, herbicide composition and application

Similar Documents

PublicationPublication DateTitle
EP2379503A1 (en)Heterocyclic diketone derivatives with herbicidal action
EP2350074A1 (en)Substituted pyridines having a herbicidal effect
DE102010042864A1 (en) Substituted thioamides with herbicidal activity
US9220268B2 (en)Herbicidal benzoxazinones
EP2325170B1 (en)Substituted quinolinones having herbicidal action
WO2011003776A2 (en)Substituted cyanobutyrates having a herbicidal effect
CN102762552B (en) 3-(3,4-Dihydro-2H-benzo[1,4]*azin-6-yl)-1H-pyrimidine-2,4-dione compounds as herbicides
CN103260412B (en)Herbicidal combinations
WO2011003775A2 (en)Substituted cyanobutyrates having a herbicidal effect
WO2011018486A2 (en)Herbicidally active composition comprising benzoxazinones
WO2011051212A1 (en)Use of heteroaromatic compounds as herbicides
WO2010139658A1 (en)Substituted pyridopyrazines with a herbicidal action
WO2011042378A1 (en)Substituted cyanobutyrates having herbicidal effect
HUE028210T2 (en)Substituted pyridines having herbicidal activity
WO2010066677A2 (en)Herbicidal mixtures
WO2011098417A1 (en)Substituted cyanobutyrates having herbicidal action
WO2011067184A1 (en)3- (4, 5 -dihydroisoxazol- 5 -yl) benzoylpyrazole compounds and mixtures thereof with safeners
EP2474226A1 (en)Herbicidally active composition comprising cyanobutyrates
DE102011080568A1 (en)New substituted cyanobutyrate compounds useful for combating weeds in culture plants e.g. cotton, rice, maize or wheat
DE102010042867A1 (en)Use of heterocyclic compounds as herbicides and for controlling undesirable plants in culture of useful plants e.g. wheat, barley, rye, oats, millet and rice

Legal Events

DateCodeTitleDescription
121Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number:10787364

Country of ref document:EP

Kind code of ref document:A1

NENPNon-entry into the national phase

Ref country code:DE

122Ep: pct application non-entry in european phase

Ref document number:10787364

Country of ref document:EP

Kind code of ref document:A1
[8]ページ先頭
©2009-2025 Movatter.jp