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AR115984A1 - 1,2-DITIOLONE COMPOUNDS AND THEIR USES - Google Patents

1,2-DITIOLONE COMPOUNDS AND THEIR USES

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Publication number
AR115984A1
AR115984A1ARP190102355AARP190102355AAR115984A1AR 115984 A1AR115984 A1AR 115984A1AR P190102355 AARP190102355 AAR P190102355AAR P190102355 AARP190102355 AAR P190102355AAR 115984 A1AR115984 A1AR 115984A1
Authority
AR
Argentina
Prior art keywords
alkyl
group
cycloalkyl
hydrogen
haloalkyl
Prior art date
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ARP190102355A
Other languages
Spanish (es)
Inventor
Alexander G M Klausener
Hagalavadi M Venkatesha
Santosh Shridhar Autkar
Ruchi Garg
Rupesh Kumar Mishra
Sankha Debnath
Sambhaji Shivnath Thok
Rohit Saxena
Sandip Appaji Pujari
Original Assignee
Pi Industries Ltd
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Application filed by Pi Industries LtdfiledCriticalPi Industries Ltd
Publication of AR115984A1publicationCriticalpatent/AR115984A1/en

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Abstract

Translated fromSpanish

La presente divulga compuestos de 1,2-ditiolina de la fórmula (1), en la que, A, Cy, R, R¹, R²ᵃ y R²ᵇ tienen los mismos significados que se definen en la descripción. La presente describe además métodos para su preparación y el uso de compuestos de 1,2-ditiolona de la fórmula (1) y/o composición de los mismos para la protección de cultivos contra microorganismos fitopatógenos no deseados. Reivindicación1: Un compuesto de la fórmula (1), en la que, R se selecciona del grupo que consiste en halógeno, hidroxilo, ciano, nitro, C₁₋₆-alquilo, C₁₋₆-haloalquilo, C₁₋₆-alcoxi, C₃₋₆-cicloalquilo, C(=O)R³, C(=O)OR³ y S(O)ₙR³; R¹ se selecciona del grupo que consiste en hidrógeno, hidroxilo, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₂₋₆-alquenilo-C₁₋₃-alquilo, C₂₋₆-alquinilo-C₁₋₃-alquilo, C₁₋₆-haloalquilo, C₂₋₈-haloalquenil, C₁₋₆-alcoxi, C₁₋₆-haloalcoxi, C₃₋₆-cicloalquilo, C₃₋₆-halocicloalquilo, C₃₋₆-cicloalquilo-C₁₋₃-alquilo, bencil, C(=O)R³, C(=O)OR³ y S(O)ₙR³; A representa O, NR¹ᵃ o S; R¹ᵃ se selecciona del grupo que consiste en hidrógeno, hidroxilo, C₁₋₆-alquilo, C₁₋₆-alcoxi, C₃₋₆-cicloalquilo, C₃₋₆-cicloalquilo-C₁₋₃-alquilo, bencil, C(=O)R³, C(=O)OR³ y S(O)ₙR³; R²ᵃ y R²ᵇ se seleccionan independientemente del grupo que consiste en hidrógeno, halógeno, hidroxilo, C₁₋₆-alquilo, C₁₋₆-alcoxi, C₃₋₆-cicloalquilo, C₃₋₆-cicloalquilo-C₁₋₃-alquilo, C(=O)R³, C(=O)OR³ y S(O)ₙR³; o R²ᵃ y R²ᵇ junto con el átomo al que están unidos o junto con otros átomos seleccionados del grupo que consiste en C, N, O y S, puede formar un anillo de tres a siete miembros, que por su parte puede estar sustituido por uno o más R³; R³ se selecciona del grupo que consiste en hidrógeno, hidroxilo, C₁₋₆-alquilo, C₁₋₆-haloalquilo, C₃₋₁₀-cicloalquilo, C₃₋₁₀-halocicloalquilo y N(R⁶R⁷); R⁶ y R⁷ se seleccionan independientemente del grupo que consiste en hidrógeno, hidroxilo, C₁₋₆-alquilo, C₁₋₆-haloalquilo, C₃₋₁₀-cicloalquilo y S(O)ₙR³; todos los grupos mencionados anteriormente definidos en R¹, R² y R³ pueden llevar uno, dos, tres o cuatro sustituyentes idénticos o diferentes seleccionados del grupo que consiste en halógeno, ciano, nitro, amino, hidroxilo, C₁₋₆-alquilo, C₁₋₆-haloalquilo, C₁₋₆-alcoxi y C₁₋₆-haloalcoxi; Cy representa C₃₋₁₀-carbociclilo fusionado o no fusionado o un grupo C₃₋₁₀-heterociclilo que opcionalmente puede estar sustituidos por uno o más grupos de R⁴; R⁴ se selecciona independientemente del grupo que consiste en hidrógeno, halógeno, hidroxilo, ciano, nitro, C₁₋₆-alquilo, C₂₋₈-alquenilo, C₂₋₈-alquinilo, C₁₋₆-haloalquilo, C₂₋₈-haloalquenil, C₁₋₆-alcoxi, C₂₋₈-alqueniloxi, C₂₋₈-alquiniloxi, C₁₋₆-haloalcoxi, C₂₋₈-haloalqueniloxi, C₂₋₈-haloalquiniloxi, C₁₋₆-alquiltio, C₂₋₈-alqueniltio, C₂₋₈-alquiniltio, C₁₋₆-haloalquiltio, C₂₋₈-haloalqueniltio, C₃₋₁₀-cicloalquilo, C₄₋₁₀-cicloalquenil, C₃₋₁₀-cicloalquiloxi, C₄₋₁₀-cicloalqueniloxi, C₃₋₁₀-cicloalquiltio, C₄₋₁₀-cicloalqueniltio, C₃₋₁₀-cicloalquilo-C₁₋₆-alquilo, C₃₋₁₀-cicloalquilo-C₁₋₆-alquiloxi, C₃₋₁₀-cicloalquilo-C₁₋₆-alquiltio, C₁₋₈-alquilo-S(O)ₙR³, N(R⁶R⁷), C(=O)R³, C(=O)OR³, S(O)ₙR³, OS(O)ₙR³, S(O)ₙ-C₆₋₁₀-arilo, S(O)ₙ-C₇₋₁₉-aralquilo, C₆₋₁₀-ariloxi, C₆₋₁₀-arilo y C₃₋₁₀-heterociclilo; todos los grupos mencionados anteriormente pueden estar sustituidos por uno o más grupos seleccionados del grupo que consiste en halógeno R’’, OR’’, SR’’, N(R’’)₂, Si(R’’)₃, COOR’’, CN, y CON(R’’)₂; o dos R⁴ junto con los átomos a los que están unidos o junto con otros átomos seleccionados del grupo que consiste en C, N, O, S y que incluyen opcionalmente de 1 a 3 miembros del anillo seleccionados del grupo que consiste en C(=O), C(=S), S(O)ₙ y Si(R’)₂, pueden formar un anillo de 3 a 7 miembros, que por su parte puede estar sustituido por uno o más R⁵; R⁵ se selecciona independientemente del grupo que consiste en hidrógeno, halógeno, ciano, nitro, C₁₋₆-alquilo, C₂₋₈-alquenilo, C₂₋₈-alquinilo, C₁₋₆-haloalquilo, C₂₋₈-haloalquenil, C₂₋₈-haloalquinil, C₃₋₆-cicloalquilo, C(=O)R’’, C(=O)OR’’, OR’’, N(R’’)₂ y S(O)ₙR’’; R’’ se selecciona del grupo que consiste en hidrógeno, C₁₋₆-alquilo, C₁₋₆-haloalquilo, C₃₋₈-cicloalquilo y N(R’)₂; en el que dichos grupos pueden estar opcionalmente sustituidos por uno o más grupos seleccionados del grupo que consiste en halógeno, R’, OR’, SR’, NR’₂, Si(R’)₃, COOR’, CN, CONR’₂ y C₅₋₁₂-arilo que están opcionalmente sustituidos por uno o más R’; R’ se selecciona del grupo que consiste en hidrógeno, halógeno, C₁₋₆-alquilo y C₃₋₆-cicloalquilo; n y m representan números enteros en los que n = 0 - 2, m = 1 - 2; o sus sales, isómeros / isómeros estructurales, estereoisómeros, diastereoisómeros, enantiómeros, tautómeros, polimorfos, complejos metálicos, S-óxido u N-óxidos agrícolamente aceptables; siempre que dicho compuesto de la fórmula (1) no sea 5-(bencilamino)-4-cloro-3H-1,2-ditiol-3-tiona.The present discloses 1,2-dithioline compounds of formula (1), wherein, A, Cy, R, R¹, R²ᵃ and R²ᵇ have the same meanings as defined in the description. The present further describes methods for their preparation and use of 1,2-dithiolone compounds of formula (1) and / or composition thereof for the protection of crops against unwanted phytopathogenic microorganisms. Claim 1: A compound of formula (1), wherein, R is selected from the group consisting of halogen, hydroxyl, cyano, nitro, C₁₋₆-alkyl, C₁₋₆-haloalkyl, C₁₋₆-alkoxy, C₃ ₋₆-cycloalkyl, C (= O) R³, C (= O) OR³ and S (O) ₙR³; R¹ is selected from the group consisting of hydrogen, hydroxyl, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkynyl, C₂₋₆-alkenyl-C₁₋₃-alkyl, C₂₋₆-alkynyl-C₁₋ ₃-alkyl, C₁₋₆-haloalkyl, C₂₋₈-haloalkenyl, C₁₋₆-alkoxy, C₁₋₆-haloalkoxy, C₃₋₆-cycloalkyl, C₃₋₆-halocycloalkyl, C₃₋₆-cycloalkyl-C₁₋₃- alkyl, benzyl, C (= O) R³, C (= O) OR³ and S (O) ₙR³; A represents O, NR¹ᵃ or S; R¹ᵃ is selected from the group consisting of hydrogen, hydroxyl, C₁₋₆-alkyl, C₁₋₆-alkoxy, C₃₋₆-cycloalkyl, C₃₋₆-cycloalkyl-C₁₋₃-alkyl, benzyl, C (= O) R³ , C (= O) OR³ and S (O) ₙR³; R²ᵃ and R²ᵇ are independently selected from the group consisting of hydrogen, halogen, hydroxyl, C₁₋₆-alkyl, C₁₋₆-alkoxy, C₃₋₆-cycloalkyl, C₃₋₆-cycloalkyl-C₁₋₃-alkyl, C (= O) R³, C (= O) OR³ and S (O) ₙR³; or R²ᵃ and R²ᵇ together with the atom to which they are attached or together with other atoms selected from the group consisting of C, N, O and S, can form a three to seven membered ring, which in turn can be substituted by one or more R³; R³ is selected from the group consisting of hydrogen, hydroxyl, C₁₋₆-alkyl, C₁₋₆-haloalkyl, C₃₋₁₀-cycloalkyl, C₃₋₁₀-halocycloalkyl, and N (R⁶R⁷); R⁶ and R⁷ are independently selected from the group consisting of hydrogen, hydroxyl, C₁₋₆-alkyl, C₁₋₆-haloalkyl, C₃₋₁₀-cycloalkyl, and S (O) ₙR³; all the aforementioned groups defined in R¹, R² and R³ may carry one, two, three or four identical or different substituents selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, C₁₋₆-alkyl, C₁₋₆ -haloalkyl, C₁₋₆-alkoxy and C₁₋₆-haloalkoxy; Cy represents fused or unfused C₃₋₁₀-carbocyclyl or a C₃₋₁₀-heterocyclyl group that may optionally be substituted by one or more R⁴ groups; R⁴ is independently selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, nitro, C₁₋₆-alkyl, C₂₋₈-alkenyl, C₂₋₈-alkynyl, C₁₋₆-haloalkyl, C₂₋₈-haloalkenyl, C₁ ₋₆-alkoxy, C₂₋₈-alkenyloxy, C₂₋₈-alkynyloxy, C₁₋₆-haloalkoxy, C₂₋₈-haloalkenyloxy, C₂₋₈-haloalkynyloxy, C₁₋₆-alkylthio, C₂₋₈-alkenylthio, C₂₋₈ -alkynylthio, C₁₋₆-haloalkylthio, C₂₋₈-haloalkenylthio, C₃₋₁₀-cycloalkyl, C₄₋₁₀-cycloalkenyl, C₃₋₁₀-cycloalkyloxy, C₄₋₁₀-cycloalkenyloxy, C₃₋₁₀-cycloalkylthio, C₄₋₁₀-cycloalkenylthio , C₃₋₁₀-cycloalkyl-C₁₋₆-alkyl, C₃₋₁₀-cycloalkyl-C₁₋₆-alkyloxy, C₃₋₁₀-cycloalkyl-C₁₋₆-alkylthio, C₁₋₈-alkyl-S (O) ₙR³, N (R⁶R⁷), C (= O) R³, C (= O) OR³, S (O) ₙR³, OS (O) ₙR³, S (O) ₙ-C₆₋₁₀-aryl, S (O) ₙ-C₇₋ ₁₉-aralkyl, C₆₋₁₀-aryloxy, C₆₋₁₀-aryl and C₃₋₁₀-heterocyclyl; all the groups mentioned above may be substituted by one or more groups selected from the group consisting of halogen R ", OR", SR ", N (R") ₂, Si (R ") ₃, COOR ' ', CN, and CON (R' ') ₂; or two R⁴ together with the atoms to which they are attached or together with other atoms selected from the group consisting of C, N, O, S and optionally including 1 to 3 ring members selected from the group consisting of C (= O), C (= S), S (O) ₙ and Si (R ') ₂, can form a ring with 3 to 7 members, which in turn can be substituted by one or more R⁵; R⁵ is independently selected from the group consisting of hydrogen, halogen, cyano, nitro, C₁₋₆-alkyl, C₂₋₈-alkenyl, C₂₋₈-alkynyl, C₁₋₆-haloalkyl, C₂₋₈-haloalkenyl, C₂₋₈ -haloalkynyl, C₃₋₆-cycloalkyl, C (= O) R ", C (= O) OR", OR ", N (R") ₂ and S (O) ₙR "; R '' is selected from the group consisting of hydrogen, C₁₋₆-alkyl, C₁₋₆-haloalkyl, C₃₋₈-cycloalkyl, and N (R ')'; wherein said groups may be optionally substituted by one or more groups selected from the group consisting of halogen, R ', OR', SR ', NR'₂, Si (R') ₃, COOR ', CN, CONR'₂ and C₅₋₁₂-aryl that are optionally substituted by one or more R '; R 'is selected from the group consisting of hydrogen, halogen, C₁₋₆-alkyl, and C₃₋₆-cycloalkyl; n and m represent integers where n = 0 - 2, m = 1 - 2; or their salts, isomers / structural isomers, stereoisomers, diastereoisomers, enantiomers, tautomers, polymorphs, metal complexes, S-oxide or N-oxides agriculturally acceptable; provided that said compound of formula (1) is not 5- (benzylamino) -4-chloro-3H-1,2-dithiol-3-thione.

ARP190102355A2018-08-172019-08-16 1,2-DITIOLONE COMPOUNDS AND THEIR USESAR115984A1 (en)

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