本発明は、殺虫活性を有する新規な化合物、その製造方法、生産菌株、及び、それを有効成分とする農園芸用殺虫剤に関する。 The present invention relates to a novel compound having insecticidal activity, a production method thereof, a production strain, and an agricultural and horticultural insecticide containing the same as an active ingredient.
従来、多くの農園芸用殺虫剤が知られているが、薬剤抵抗性や安全性などの問題から、より有効で安全に使える剤が必要とされている。
PF1364物質は、Austin系新規化合物である。類縁物質であるAustinは、アスペルギルス（Aspergillus）属の生産する代謝産物として（非特許文献１）、Dehydroaustinは、ぺニシリウム（Penicillium）属、及び、アスペルギルス（Aspergillus）属の生産する代謝産物として（非特許文献２）報告されている。
また、Austin類縁物質が、カイコに対して痙攣作用を有する化合物の、痙攣作用を増強する作用を有することが報告されているが（非特許文献３、非特許文献４、非特許文献５）、これらAustin類縁物質の農業害虫に対する殺虫活性については報告がない。さらに、Journal of the Brazilian Chemical Society, 2003, 14（5）, 722-727（非特許文献６）、Chemistry & Biodiversity, 2008, 5（2）, 341-345（非特許文献７）には、Austin類、とりわけDehydroaustinの、蚊の幼虫に対する活性が強いことが報告されているが、やはり農業害虫に対する殺虫活性についての報告はない。Conventionally, many agricultural and horticultural insecticides are known. However, due to problems such as drug resistance and safety, more effective and safer agents are required.
PF1364 substance is a new Austin compound. Austin, which is a related substance, is a metabolite produced by the genus Aspergillus (Non-patent Document 1), and Dehydroaustin is a metabolite produced by the genus Penicillium and the genus Aspergillus (non-patent document 1). Patent Document 2) has been reported.
Further, it has been reported that an Austin-related substance has an action of enhancing the convulsant action of a compound having a convulsant action on silkworms (Non-patent Document 3, Non-patent Document 4, Non-patent Document 5). There are no reports on the insecticidal activity of these Austin-related substances against agricultural pests. Furthermore, in the Journal of the Brazilian Chemical Society, 2003, 14 (5), 722-727 (Non-Patent Document 6), Chemistry & Biodiversity, 2008, 5 (2), 341-345 (Non-Patent Document 7), Austin It has been reported that Dehydroaustin, particularly mosquitoes, has strong activity against mosquito larvae, but there is no report on insecticidal activity against agricultural pests.
これまでに多くの農園芸用殺虫剤が報告されているが、いずれも薬剤抵抗性虫種や難防除虫種が認められ、新しい殺虫剤が望まれている。
本発明の目的は、殺虫活性を有する新規な化合物、その製造方法、生産菌株、及び、それを有効成分とする農園芸用殺虫剤を提供することである。Many agricultural and horticultural insecticides have been reported so far, and drug resistant insect species and difficult-to-control insect species have been recognized, and new insecticides are desired.
An object of the present invention is to provide a novel compound having insecticidal activity, a production method thereof, a production strain, and an agricultural and horticultural insecticide containing the same as an active ingredient.
本発明者らは、新規な農園芸用殺虫剤を鋭意探索した結果、Aspergillus sp.の生産する式（1）で示される新規なPF1364物質（以下、PF1364と称す）が農園芸用殺虫剤として有用な殺虫活性を示すことを見出した。 As a result of earnest search for a novel agricultural and horticultural insecticide, the present inventors have found that a novel PF1364 substance (hereinafter referred to as PF1364) represented by the formula (1) produced by Aspergillus sp. It has been found that it exhibits useful insecticidal activity.
すなわち、本発明は、下記式（1） That is, the present invention provides the following formula (1)
（1）
で表されるPF1364物質、そのエナンチオマー、それらの混合物、または、その溶媒和物に関するものである。(1)
The PF1364 substance represented by the formula, its enantiomer, a mixture thereof, or a solvate thereof.
また、本発明は前記の式（1）で示すPF1364物質、そのエナンチオマー、それらの混合物、または、その溶媒和物を有効成分として含んでなる農園芸用殺虫剤を提供するものである。 The present invention also provides an agricultural and horticultural insecticide comprising the PF1364 substance represented by the formula (1), an enantiomer thereof, a mixture thereof, or a solvate thereof as an active ingredient.
さらに、本発明はAspergillus属に属しPF1364物質を生産する能力を有する微生物を培養し、その培養物からPF1364物質を採取することを特徴とする、PF1364物質の製造方法に関するものであり、Aspergillus属に属しPF1364物質を生産する能力を有する微生物が、Aspergillus ustus、または、Aspergillus pseudodeflectusであるPF1364物質の製造方法、さらには、Aspergillus属に属しPF1364物質を生産する能力を有する微生物が、Aspergillus sp. PF1364菌株であるPF1364物質の製造方法を提供するものである。 Furthermore, the present invention relates to a method for producing a PF1364 substance, characterized by culturing a microorganism belonging to the genus Aspergillus and capable of producing a PF1364 substance, and collecting the PF1364 substance from the culture. A method for producing a PF1364 substance, wherein the microorganism having the ability to produce a PF1364 substance is Aspergillus ustus or Aspergillus pseudodeflectus, and further, a microorganism having the ability to produce a PF1364 substance belonging to the genus Aspergillus is an Aspergillus sp. PF1364 strain A method for producing the PF1364 substance is provided.
また、本発明の別の態様としては、前記の式（1）で示すPF1364物質を生産する能力を有するAspergillus属に属する微生物に関するものである。さらにはPF1364物質を生産する能力を有するAspergillus属に属する微生物がAspergillus ustus、または、Aspergillus pseudodeflectus、また、PF1364物質を生産する能力を有するAspergillus属に属する微生物がAspergillus sp. PF1364菌株、または、その変異株である微生物を提供するものである。 Another embodiment of the present invention relates to a microorganism belonging to the genus Aspergillus having the ability to produce the PF1364 substance represented by the above formula (1). Furthermore, the microorganism belonging to the genus Aspergillus having the ability to produce the PF1364 substance is Aspergillus ustus or Aspergillus pseudodeflectus, and the microorganism belonging to the genus Aspergillus having the ability to produce the PF1364 substance is an Aspergillus sp. PF1364 strain or a mutation thereof It provides microorganisms that are strains.
本発明のPF1364、その製造方法、生産菌株、を提供することで、優れた殺虫活性かつ安全な農薬園芸用殺虫剤を提供することが出来る。 By providing PF1364 of the present invention, its production method, and production strain, it is possible to provide an insecticidal horticultural insecticide with excellent insecticidal activity and safety.
PF1364の理化学的性状を以下に示す。なお、理化学的性状の測定方法は次のとおりである。
１．色および形状は外観から判断した。
２．マススペクトラムの測定はJMS-700質量分析器（日本電子）とZQ-4000（Waters）を用いた。
イオンの検出は、大気圧イオン化法のエレクトロンスプレー法（ES-MSと記す）、高速原子衝突法（FAB-MSと記す）で行った。
３．ＮＭＲスペクトラムの測定は、JNM-LA400（日本電子）を用いた。
４．紫外線吸収波長は島津紫外可視分光光度計UV-1800シリーズを用いて行った。The physicochemical properties of PF1364 are shown below. The method for measuring physicochemical properties is as follows.
1. The color and shape were judged from the appearance.
2. The mass spectrum was measured using a JMS-700 mass spectrometer (JEOL) and ZQ-4000 (Waters).
Ions were detected by the atmospheric pressure ionization electron spray method (ES-MS) and the fast atom collision method (FAB-MS).
3. The NMR spectrum was measured using JNM-LA400 (JEOL).
4). The ultraviolet absorption wavelength was measured using Shimadzu UV-Visible spectrophotometer UV-1800 series.
＜PF1364物質の理化学的性状＞
１）色および形状：白色粉末/結晶
２）マススペクトル：（ES-MS）M/Z 617(M+H)+、(FAB-MS）M/Z 617(M+H)+ M/Z 639(M+H+Na)+
３）分子式：C31H36O13
４）1H -NMRスペクトル（400MHz、CDCl3）
δ（ppm）：1.41（3H,s）、1.45（3H,s）、1.47（3H,s）、1.70〜1.94（8H,m）、2.08（3H,s）、2.29（1H,dd）、3.00（1H,dd）、4.30（1H,dd）、5.21（H,q）、5.50（1H,dd）、5.82（1H,d）、5.93（1H,s）、5.93（1H,d）、6.87（1H,m）
５）13C -NMRスペクトル（100MHz、CDCl3）
δ（ppm）：11.8、12.2、13.9、14.7、16.0、20.8、23.3、27.3、35.5、37.0、45.9、61.3、64.6、65.4、67.0、75.8、77.3、83.3、85.9、89.7、93.5、125.1、127.1、137.6、140.6、163.6、164.1、166.5、168.4、174.6、191.5
６）紫外線吸収スペクトル
λmax（MeOH）：218nm、202nm<Physical and chemical properties of PF1364>
1) Color and shape: white powder / crystal 2) Mass spectrum: (ES-MS) M / Z 617 (M + H)+ , (FAB-MS) M / Z 617 (M + H)+ M / Z 639 (M + H + Na)+
3) Molecular formula: C31 H36 O13
4)1 H -NMR spectrum (400 MHz, CDCl?)
δ (ppm): 1.41 (3H, s), 1.45 (3H, s), 1.47 (3H, s), 1.70 to 1.94 (8H, m), 2.08 (3H, s), 2.29 (1H, dd), 3.00 (1H, dd), 4.30 (1H, dd), 5.21 (H, q), 5.50 (1H, dd), 5.82 (1H, d), 5.93 (1H, s), 5.93 (1H, d), 6.87 ( 1H, m)
5)13 C-NMR spectrum (100 MHz, CDCl 3)
δ (ppm): 11.8, 12.2, 13.9, 14.7, 16.0, 20.8, 23.3, 27.3, 35.5, 37.0, 45.9, 61.3, 64.6, 65.4, 67.0, 75.8, 77.3, 83.3, 85.9, 89.7, 93.5, 125.1, 127.1 , 137.6, 140.6, 163.6, 164.1, 166.5, 168.4, 174.6, 191.5
6) UV absorption spectrum λmax (MeOH): 218 nm, 202 nm
式（1）で示されるPF1364は、PF1364の生産能を有する微生物を培養し、その培養物から採取することによって得ることができる。
従って本発明のもう一つの態様として、前記式（1）で示されるPF1364生産菌を培養し、その培養物よりPF1364を採取することを特徴とするPF1364の製造方法を提供するものである。
式（1）で示されるPF1364生産菌としては、Aspergillus属の微生物が挙げられる。さらに好ましくは、Aspergillusustus、または、Aspergillus pseudodeflectus などが挙げられる。一例としては、Aspergillus sp. PF1364株が挙げられる。PF1364株は独立行政法人産業技術総合研究所 特許生物寄託センターに寄託されており、その受領番号はＦＥＲＭ ＡＰ−２１５９７である。
上記新規物質PF1364は、Aspergillus sp. PF1364株を培養し、PF1364を生産・蓄積させて、この培養物よりPF1364を採取することにより得られる。PF1364の生産菌であるAspergillus sp. PF1364株は、長崎県五島列島で採集した土壌試料から新たに分離された菌株である。次の遺伝的、及び、菌学的性質を有する。PF1364 represented by the formula (1) can be obtained by culturing a microorganism capable of producing PF1364 and collecting it from the culture.
Therefore, as another embodiment of the present invention, there is provided a method for producing PF1364 characterized by culturing a PF1364-producing bacterium represented by the above formula (1) and collecting PF1364 from the culture.
Examples of the PF1364 producing bacterium represented by the formula (1) include microorganisms belonging to the genus Aspergillus. More preferably, Aspergillusustus, Aspergillus pseudodeflectus, etc. are mentioned. An example is Aspergillus sp. PF1364 strain. The PF1364 strain has been deposited with the Patent Organism Depositary, National Institute of Advanced Industrial Science and Technology, and its receipt number is FERM AP-21597.
The novel substance PF1364 can be obtained by culturing Aspergillus sp. PF1364 strain, producing and accumulating PF1364, and collecting PF1364 from this culture. Aspergillus sp. PF1364, a strain producing PF1364, is a newly isolated strain from a soil sample collected in the Goto Islands, Nagasaki Prefecture. Has the following genetic and mycological properties:
（１）PF1364株の遺伝情報による相同性検索結果
菌株の同定に必要な以下の２種類の遺伝情報の取得を実施した。
＜Aspergillus sp. PF1364の28S rDNA-D1/D2領域の塩基配列＞
GCATATCAATAAGCGGAGGAAAAGAAACCAACCGGGATTGCCTCAGTAACGGCGAGTGAAGCGGCAAGAGCTCAAATTTGAAATCTGGCCCCTCCGGGGTCCGAGTTGTAATTTGCAGAGGATGCTTCGGGTGCGGCCCCTGTCTAAGTGCCCTGGAACGGGCCATCAGAGAGGGTGAGAATCCCGTCTTGGGCAGGGTGCCCGTGCCCGTGTGAAGCTCCTTCGACGAGTCGAGTTGTTTGGGAATGCAGCTCTAAATGGGTGGTAAATTTCATCTAAAGCTAAATACCGGCCGGAGACCGATAGCGCACAAGTAGAGTGATCGAAAGATGAAAAGCACTTTGAAAAGAGAGTTAAACAGCACGTGAAATTGTTGAAaGGGAAGCGCTTGCGACCAGACTCGGCCCCGGGGTTCAGCCAGCACTCGTGCTGGTGTACTTCCCCGGGGGCGGGCCAGCGTCGGTTTGGGCGGCCGGTCAAAGGCCCCAGGAATGTGTCGCCCTCCGGGGCGTCTTATAGCCTGGGGTGCAATGCGGCCAGCCCGGACCGAGGAACGCGCTTCGGCACGGACGCTGGCGTAATGGTCGCAAACGACCCGTCTTGAAACACGGACC(1) Homology search result based on genetic information of PF1364 strain The following two types of genetic information necessary for identification of the strain were obtained.
<A base sequence of 28S rDNA-D1/D2 region of Aspergillus sp. PF1364>
GCATATCAATAAGCGGAGGAAAAGAAACCAACCGGGATTGCCTCAGTAACGGCGAGTGAAGCGGCAAGAGCTCAAATTTGAAATCTGGCCCCTCCGGGGTCCGAGTTGTAATTTGCAGAGGATGCTTCGGGTGCGGCCCCTGTCTAAGTGCCCTGGAACGGGCCATCAGAGAGGGTGAGAATCCCGTCTTGGGCAGGGTGCCCGTGCCCGTGTGAAGCTCCTTCGACGAGTCGAGTTGTTTGGGAATGCAGCTCTAAATGGGTGGTAAATTTCATCTAAAGCTAAATACCGGCCGGAGACCGATAGCGCACAAGTAGAGTGATCGAAAGATGAAAAGCACTTTGAAAAGAGAGTTAAACAGCACGTGAAATTGTTGAAaGGGAAGCGCTTGCGACCAGACTCGGCCCCGGGGTTCAGCCAGCACTCGTGCTGGTGTACTTCCCCGGGGGCGGGCCAGCGTCGGTTTGGGCGGCCGGTCAAAGGCCCCAGGAATGTGTCGCCCTCCGGGGCGTCTTATAGCCTGGGGTGCAATGCGGCCAGCCCGGACCGAGGAACGCGCTTCGGCACGGACGCTGGCGTAATGGTCGCAAACGACCCGTCTTGAAACACGGACC
一般的に属レベルで分類が可能とされる28SリボソームRNAの遺伝情報から相同性検索を実施（国際塩基配列データベースBLAST検索による）した結果、子のう菌類の一種であるAspergillus ustus UWFP546（アクセッション番号AY216676）、およびAspergillus pseudodeflectus NRRL6135（アクセッション番号AF433123）と99.8％の相同率を示した。相同性検索で得られた上位の塩基配列をもとに作成した系統樹において、Aspergillus sp. PF1364株の28S rDNA-D1/D2領域の塩基配列はAspergillus ustus およびAspergillus pseudodeflectusと同一の系統枝を形成した。 Aspergillus ustus UWFP546 (accession) as a result of homology search (by international base sequence database BLAST search) from genetic information of 28S ribosomal RNA that can generally be classified at the genus level No. AY216676) and Aspergillus pseudodeflectus NRRL6135 (Accession No. AF433123) showed a 99.8% homology. In the phylogenetic tree created based on the high-order base sequence obtained by homology search, the base sequence of 28S rDNA-D1 / D2 region of Aspergillus sp. PF1364 strain forms the same phylogenetic branch as Aspergillus ustus and Aspergillus pseudodeflectus did.
＜Aspergillus sp. PF1364のITS-5.8S rDNA領域の塩基配列＞
GGAAGTAAAAGTCGTAACAAGGTTTCCGTAGGTGAACCTGCGGAAGGATCATTACCGAGTGCAGGTCTGCCCCCGGGCAGGCCTAACCTCCCACCCGTGAATACCTGACCAACGTTGCTTCGGCGGTGCGCCCCCCCCCGGGGGTAGCCGCCGGAGACCACACCGAACCTCCTGTCTTTAGTGTTGTCTGAGCTTGATAGCAAACCTAtTAAAACTTTCAACAATGGATCTCTTGGTTCCGGCATCGATGAAGAACGCAGCGAACTGCGATAAGTAATGTGAATTGCAGAATTCAGTGAATCATCGAGTCTTTGAACGCACATTGCGCCCCCTGGCATTCCGGGGGGCATGCCTGTCCGAGCGTCATTGCTGCCCTTCAAGCCCGGCTTGTGTGTTGGGTCGTCGTCCCCCCCGGGGGACGGGCCCGAAAGGCAGCGGCGGCACCGCGTCCGGTCCTCGAGCGTATGGGGCTTTGTCACCCGCTCGATTAGGGCCGGCCGGGCGCCAGCCGGCGTCTCCAACCTTCTATTTTACCAGGtTGACCTCGGATCAGGTAGGGATACCCGCTGAACTTAAGCATATCAATAAGCGGAGGA<Base sequence of ITS-5.8S rDNA region of Aspergillus sp. PF1364>
GGAAGTAAAAGTCGTAACAAGGTTTCCGTAGGTGAACCTGCGGAAGGATCATTACCGAGTGCAGGTCTGCCCCCGGGCAGGCCTAACCTCCCACCCGTGAATACCTGACCAACGTTGCTTCGGCGGTGCGCCCCCCCCCGGGGGTAGCCGCCGGAGACCACACCGAACCTCCTGTCTTTAGTGTTGTCTGAGCTTGATAGCAAACCTAtTAAAACTTTCAACAATGGATCTCTTGGTTCCGGCATCGATGAAGAACGCAGCGAACTGCGATAAGTAATGTGAATTGCAGAATTCAGTGAATCATCGAGTCTTTGAACGCACATTGCGCCCCCTGGCATTCCGGGGGGCATGCCTGTCCGAGCGTCATTGCTGCCCTTCAAGCCCGGCTTGTGTGTTGGGTCGTCGTCCCCCCCGGGGGACGGGCCCGAAAGGCAGCGGCGGCACCGCGTCCGGTCCTCGAGCGTATGGGGCTTTGTCACCCGCTCGATTAGGGCCGGCCGGGCGCCAGCCGGCGTCTCCAACCTTCTATTTTACCAGGtTGACCTCGGATCAGGTAGGGATACCCGCTGAACTTAAGCATATCAATAAGCGGAGGA
一般的に種レベルで分類が可能とされるＩＴＳ１−５．８Ｓ−ＩＴＳ２領域のリボソームRNAの遺伝情報から相同性検索を実施（国際塩基配列データベースBLAST検索による）した結果、子のう菌類の一種であるAspergillus ustus UWFP546（アクセッション番号AF455532）、およびAspergillus pseudodeflectus NRRL6135（アクセッション番号DQ778908）と99.8％の相同率を示した。相同性検索で得られた上位の塩基配列をもとに作成した系統樹において、Aspergillus sp. PF1364株のITS-5.8S rDNA領域の塩基配列はAspergillus ustus およびAspergillus pseudodeflectusと同一の系統枝を形成した。
以上より、Aspergillus sp. PF1364株はAspergillus属Nidulantes亜属Usti節に属し、その中でもAspergillusustus またはAspergillus pseudodeflectus に近縁なAspergillus 属の一種（Aspergillus sp.）と推定された。As a result of homology search (by international base sequence database BLAST search) based on genetic information of ribosomal RNA in ITS1-5.8S-ITS2 region, which can generally be classified at the species level, Aspergillus ustus UWFP546 (accession number AF455532) and Aspergillus pseudodeflectus NRRL6135 (accession number DQ778908) showed a 99.8% homology rate. In the phylogenetic tree created based on the high-order base sequence obtained by homology search, the base sequence of ITS-5.8S rDNA region of Aspergillus sp. PF1364 strain formed the same phylogenetic branch as Aspergillus ustus and Aspergillus pseudodeflectus .
Based on the above, it was estimated that Aspergillus sp. PF1364 belongs to the Astigillus genus Nidulantes subgenus Usti section, and among them, it is a kind of Aspergillus genus (Aspergillus sp.) Closely related to Aspergillusustus or Aspergillus pseudodeflectus.
（２）PF1364株の菌学的性状
（２）−１ 生育状態
ポテトデキストロース寒天培地上で生育良く、２５℃、７日間の培養でコロニーの直径２３〜２７ｍｍに達する。淡赤色〜白色、ベルベット状、周辺部が盛り上がり、厚い菌糸層からなる。分生子は周縁部を除く全体に多数生じる。黄色の可溶性色素を産生する。裏面は暗黄色となる。
麦芽エキス寒天培地上で生育良く、２５℃、７日間の培養の培養でコロニーの直径１３〜１８ｍｍに達する。茶褐色から白色、ベルベット状、分生子は中心部に生じる。
オートミール寒天培地上で生育良く、２５℃、７日間の培養の培養でコロニーの直径３３〜３６ｍｍに達する。暗茶色、ベルベット状、平坦、薄い菌糸層からなり、分生子は全体に多数生じる。裏面は淡黄土色となる。
３７℃の培養での生育も確認されている。(2) Mycological properties of PF1364 strain
(2) -1 Growth state It grows well on a potato dextrose agar medium, and reaches a colony diameter of 23 to 27 mm after culturing at 25 ° C. for 7 days. Pale red to white, velvet shape, the peripheral part is raised, and consists of a thick mycelium layer. A large number of conidia occur throughout the whole area except the peripheral edge. It produces a yellow soluble pigment. The back side is dark yellow.
It grows well on malt extract agar medium and reaches a colony diameter of 13 to 18 mm after culturing at 25 ° C. for 7 days. Brown to white, velvet, conidia occur in the center.
It grows well on oatmeal agar medium and reaches a colony diameter of 33 to 36 mm after culturing at 25 ° C. for 7 days. It consists of dark brown, velvet-like, flat, and thin mycelium layers, and many conidia occur throughout. The back is light ocher.
Growth at 37 ° C. has also been confirmed.
（２）−２ 形態的特徴
分生子柄は１００〜２００× ３〜４．５μｍ、栄養菌糸から直立し、非分岐、無隔壁で、表面は平滑〜微棘状、無色〜茶褐色に着色している。柄の先端部が膨らみ球形〜亜球形の頂のう（８．０〜１３．０μｍ）の形成が認められ、頂のうの周縁上２/３から円筒形のメトレ（４．５〜７．５ × １．５〜２．５μｍ）が形成され、さらにその先端部から分生子形成細胞である首の短いアンプル型のフィアライド（５．０〜７．５× １．５〜２．５μｍ）が形成される２列アスペルジラムの構造を有する。分生子（２．５〜３．５μｍ）はフィアロ型で球形、1細胞、表面は微棘状〜粗面、明褐色〜茶褐色。(2) -2 Morphological features Conidial pattern is 100-200 × 3-4.5 μm, upright from vegetative mycelium, non-branching, no septum, surface is smooth to fine spine, colorless to brown Yes. The tip of the handle swells, and the formation of a spherical to sub-spherical apex (8.0 to 13.0 μm) is recognized. From 2/3 on the periphery of the apex, a cylindrical metre (4.5 to 7.7). 5 × 1.5 to 2.5 μm) is formed, and from the tip, an ampoule-type phialide (5.0 to 7.5 × 1.5 to 2.5 μm) having a short neck as conidia-forming cells is formed. It has the structure of the two-row asperdilam formed. The conidia (2.5-3.5 μm) are fiaro-type, spherical, 1 cell, the surface is fine spiny to rough, light brown to brown.
以上の菌学的性状より本菌株はAspergillus属Nidulantes亜属Usti節に属すると考えられる。本節に含まれる５種のうち、PF1364株の分生子が微棘状であることから、Aspergillus ustus またはAspergillus pseudodeflectusに絞られた。
以上の得られた遺伝情報、菌学的性状に矛盾はなく、それらの結果より、本菌株をAspergillus ustus またはAspergillus pseudodeflectusに近縁なAspergillus属Nidulantes亜属Usti節に属するアスペルギルス・スピーシーズ(Aspergillus sp.）PF1364株と呼称することにした。
Aspergillus sp. PF1364株は他のカビに見られるようにその性状が変化し易い。例えば、Aspergillus sp. PF1364株に由来する突然変異株（自然発生または誘発性）、形質接合体または遺伝子組換体であっても、PF1364を生産するものはすべて本発明に使用できる。Based on the above bacteriological properties, this strain is considered to belong to the Astigillus genus Nidulantes subgenus Usti section. Of the five species included in this section, the conidia of the PF1364 strain were microspinous, and thus were narrowed down to Aspergillus ustus or Aspergillus pseudodeflectus.
There is no contradiction in the genetic information and mycological properties obtained above, and based on these results, the strain was identified as Aspergillus sp. (Aspergillus sp. ) I decided to call it PF1364 strain.
Aspergillus sp. Strain PF1364 is susceptible to changes in its properties as seen in other molds. For example, any mutated strain (naturally occurring or inducible) derived from an Aspergillus sp. Strain PF1364, a zygote or a gene recombinant can be used in the present invention.
（３）PF1364菌株の培養方法、PF1364の精製方法
本技術の方法では、アスペルギルス・スピーシーズ(Aspergillus sp.）に属し、PF1364を生産する能力を有している菌として、例えばPF1364株を炭素源及び窒素源を含む栄養培地で培養する。
栄養源としては、従来カビの培養に利用されている公知のものが使用でき、使用する培地は天然培地または合成培地いずれでもよい。(3) Cultivation method of PF1364 strain, purification method of PF1364 In the method of the present technology, as a bacterium belonging to Aspergillus sp. And capable of producing PF1364, for example, PF1364 strain is used as a carbon source and Incubate in nutrient medium containing nitrogen source.
As the nutrient source, known ones conventionally used for mold cultivation can be used, and the medium to be used may be either a natural medium or a synthetic medium.
例えば、炭素源としては、グルコース、スクロース、水飴、デキストリン、澱粉、グリセロール、糖蜜、米、麦、コーングリッツなどの穀類等、動植物油等を使用し得る。また、窒素源としては、大豆粉、小麦胚芽、コーン・スティープ・リカー、綿実粕、肉エキス、ペプトン、酵母エキス、硫酸アンモニウム、硝酸ナトリウム、尿素等を使用し得る。その他必要に応じてナトリウム、カリウム、カルシウム、マグネシウム、コバルト、塩素、燐酸、硫酸及びその他のイオンを生成することができる無機塩類を添加することは有効である。また、菌の発育を助け、PF1364を生産するような有機物及び無機物を適当に添加することができる。さらに、培地には必要に応じて、本菌の生育やPF1364の生産を促進するビタミン類などの微量栄養素、発育促進物質、前駆物質などを適当に添加してもよい。 For example, as the carbon source, glucose, sucrose, starch syrup, dextrin, starch, glycerol, molasses, grains such as rice, wheat, corn grits, and animal and vegetable oils can be used. As the nitrogen source, soybean flour, wheat germ, corn steep liquor, cottonseed meal, meat extract, peptone, yeast extract, ammonium sulfate, sodium nitrate, urea, and the like can be used. In addition, it is effective to add inorganic salts capable of generating sodium, potassium, calcium, magnesium, cobalt, chlorine, phosphoric acid, sulfuric acid and other ions as necessary. In addition, organic substances and inorganic substances that assist the growth of bacteria and produce PF1364 can be appropriately added. Furthermore, micronutrients such as vitamins that promote the growth of this bacterium and the production of PF1364, growth promoting substances, precursors, and the like may be appropriately added to the medium as necessary.
培養は、静置培養、通常振とうまたは通気攪拌培養などの好気的条件下で行ってもよい。液体培養でのｐＨは中性付近で培養を行うのが好ましい。培養に適当な温度は２５〜４０℃であるが、多くの場合２５〜３０℃付近で培養する。PF1364の生産は、培地や培養条件によって異なるが、静置培養、振盪培養、タンク培養のいずれにおいても、通常２〜２０日間でその蓄積が最高に達する。培養物中、目的とするPF1364の蓄積が最高になった時に培養を停止する。これらの培地組成、培地の液性、培養温度、攪拌速度、通気量などの培養条件は使用する菌株の種類や外部の条件などに応じて好ましい結果が得られるように適宜調節、選択されることはいうまでもない。液体培養において、発泡があるときは、シリコン油、植物油、界面活性剤などの消泡剤を適宜使用できる。このようにして得られた培養物に蓄積されるPF1364は、菌体内および培養濾液中に含有されるので、培養物の溶媒抽出を行い、PF1364を採取するのが有利である。 The culture may be performed under aerobic conditions such as stationary culture, normal shaking, or aeration and agitation culture. It is preferable to perform the culture in the vicinity of neutral pH in liquid culture. The temperature suitable for the culture is 25 to 40 ° C., but in many cases, the culture is performed at around 25 to 30 ° C. The production of PF1364 varies depending on the culture medium and culture conditions, but in any of stationary culture, shaking culture and tank culture, the accumulation usually reaches its maximum in 2 to 20 days. The culture is stopped when the target accumulation of PF1364 reaches the maximum. The culture conditions such as medium composition, medium liquidity, culture temperature, stirring speed, and aeration rate should be adjusted and selected as appropriate according to the type of strain used and external conditions. Needless to say. In liquid culture, when there is foaming, an antifoaming agent such as silicone oil, vegetable oil, or surfactant can be used as appropriate. Since PF1364 accumulated in the culture thus obtained is contained in the cells and in the culture filtrate, it is advantageous to extract the PF1364 by solvent extraction of the culture.
培養物からの精製方法としては、例えば、培養物より適当な有機溶媒を用いて式（1）で示される化合物を抽出し、該抽出物について吸着剤を用いた吸脱着法、ゲル濾過剤を用いた分子分配法等を用いて精製することが挙げられる。より具体的には、有効成分を含む培養物を例えば酢酸エチルにより抽出し、抽出液を減圧濃縮し、該抽出物を少量のクロロホルムに溶解し、クロロホルムで平衡化したシリカゲルカラムを用いて、クロロホルム／メタノールの溶媒でクロマトグラフィーを行う。そして、活性物質を含む溶出画分を減圧濃縮し、これをメタノールに再溶解して、メタノールで平衡化したセファデックスＬＨ−２０（ファルマシアファインケミカルズ社製）によるゲル濾過、あるいはヘキサン／酢酸エチルの溶媒で平衡化したシリカゲルカラムを用いて、ヘキサン／酢酸エチルの溶媒でクロマトグラフィーを行い、得られた活性化合物群を、ＯＤＳカラムなどを用いた逆相系、あるいはシリカゲルカラムなどを用いた順相系で、高速液体クロマトグラフィーを行うなどにより目的とする化合物を得ることができる。 As a purification method from the culture, for example, a compound represented by the formula (1) is extracted from the culture using an appropriate organic solvent, and the extract is subjected to an adsorption / desorption method using an adsorbent, a gel filtration agent Purification may be performed using the molecular partitioning method used. More specifically, the culture containing the active ingredient is extracted with, for example, ethyl acetate, the extract is concentrated under reduced pressure, the extract is dissolved in a small amount of chloroform, and the mixture is equilibrated with chloroform. Chromatography with / methanol solvent. Then, the elution fraction containing the active substance is concentrated under reduced pressure, redissolved in methanol, gel filtration with Sephadex LH-20 (Pharmacia Fine Chemicals) equilibrated with methanol, or solvent of hexane / ethyl acetate. Chromatography with a hexane / ethyl acetate solvent using a silica gel column equilibrated in step 1), and the resulting active compound group is converted into a reverse phase system using an ODS column or the like, or a normal phase system using a silica gel column or the like. The target compound can be obtained by performing high performance liquid chromatography.
本発明化合物であるPF1364の溶媒和物の溶媒とは以下のものが挙げられる。
水、メタノール、エタノール、ｎ−プロパノール、ｉ−プロパノール、ｎ−ブタノール、２−ブタノール、イソブタノール、ｔｅｒｔ−ブタノール、アセトン、アセトニトリル、ｎ−ヘキサン、ｎ−ヘプタン、酢酸エチル、酢酸ブチル、クロロホルムなどである。
好ましい溶媒和物は、水和物、メタノール和物、エタノール和物、酢酸エチル和物などであり、さらに好ましくは水和物である。Examples of the solvent of the solvate of PF1364 which is the compound of the present invention include the following.
With water, methanol, ethanol, n-propanol, i-propanol, n-butanol, 2-butanol, isobutanol, tert-butanol, acetone, acetonitrile, n-hexane, n-heptane, ethyl acetate, butyl acetate, chloroform, etc. is there.
Preferred solvates are hydrates, methanol solvates, ethanol solvates, ethyl acetate solvates, and the like, more preferably hydrates.
本発明のPF1364は、各種の害虫に対して優れた防除効果（殺虫活性）を示し、農園芸用殺虫剤として利用することができる。PF1364が防除効果を示す虫種としては、鱗翅目害虫（例えば、ハスモンヨトウ、シロイチモジヨトウ、アワヨトウ、ヨトウガ、タマナヤガ、トリコプルシア属、ヘリオティス属、ヘリコベルパ属等のヤガ類、ニカメイガ、コブノメイガ、ヨーロピアンコーンボーラー、ハイマダラノメイガ、シバツトガ、ワタノメイガ、ノシメマダラノメイガ等のメイガ類、モンシロチョウ等のシロチョウ類、アドキソフィエス属、ナシヒメシンクイ、コドリンガ等のハマキガ類、モモシンクイガ等のシンクイガ類、リオネティア属等のハモグリガ類、リマントリア属、ユープロクティス属等のドクガ類、コナガ等のスガ類、ワタアカミムシ等のキバガ類、アメリカシロヒトリ等のヒトリガ類、イガ、コイガ等のヒロズコガ類等）、半翅目害虫（例えば、モモアカアブラムシ、ワタアブラムシ等のアブラムシ類、ヒメトビウンカ、トビイロウンカ、セジロウンカ等のウンカ類、ツマグロヨコバイ等のヨコバイ類、アカヒゲホソミドリカスミカメ、チャバネアオカメムシ、ミナミアオカメムシ、ホソヘリカメムシ等のカメムシ類、オンシツコナジラミ、タバココナジラミ等のコナジラミ類、クワシロカイガラムシ、クワコナカイガラムシ等のカイガラムシ類、グンバイムシ類、キジラミ類等）、鞘翅目害虫（例えば、メイズウィービル、イネミズゾウムシ、アズキゾウムシ等のゾウムシ類、チャイロコメノゴミムシダマシ等のゴミムシダマシ類、ドウガネブイブイ、ヒメコガネ等のコガネムシ類、キスジノミハムシ、ウリハムシ、コロラドポテトハムシ、ウェスタンコーンルートワーム、サザンコーンルートワーム等のハムシ類、イネドロオイムシ、アオバアリガタハネカクシ、シンクイムシ類、ニジュウヤホシテントウ等のエピラクナ類、カミキリムシ類等）、ダニ目（例えば、ナミハダニ、カンザワハダニ、ミカンハダニ、リンゴハダニ、オリゴニカス属等のハダニ類、トマトサビダニ、ミカンサビダニ、チャノサビダニ等のフシダニ類、チャノホコリダニ等のホコリダニ類、コナダニ類等）、膜翅目害虫（例えば、カブラハバチ等のハバチ類等）、直翅目害虫（例えば、バッタ類等）、双翅目害虫（例えばイエバエ類、イエカ類、ハマダラカ類、ユスリカ類、クロバエ類、ニクバエ類、ヒメイエバエ類、ハナバエ類、マメハモグリバエ、トマトハモグリバエ、ナスハモグリバエ等のハモグリバエ類、ミバエ類、ノミバエ類、ショウジョウバエ類、チョウバエ類、ブユ類、アブ類、サシバエ類等）、アザミウマ目害虫（例えば、ミナミキイロアザミウマ、ミカンキイロアザミウマ、ネギアザミウマ、ハナアザミウマ、チャノキイロアザミウマ、ヒラズハナアザミウマ、カキクダアザミウマ等）、植物寄生性線虫（例えば、ネコブセンチュウ類、ネグサレセンチュウ類、シストセンチュウ類、イネシンガレセンチュウ等のアフェレンコイデス類、マツノザイセンチュウ等） などである。好ましくは、半翅目、アザミウマ目害虫である。 PF1364 of the present invention exhibits an excellent control effect (insecticidal activity) against various pests and can be used as an agricultural and horticultural insecticide. Species of which PF1364 exhibits a controlling effect include lepidopterous insects (for example, Spodoptera litura, Shirochimojiyoto, Awayo, Yotoga, Tamanayaga, Trichopulsia, Heliotis, Helicoberpa, etc., Nikameiga, Konoumeiga, European corn borer, Common moth, Shibatatsuga, Watanogaiga, Noshimemadaranoga, etc. Species of the genus Kutis, Suga such as the longhorn beetle, Kibata such as the cotton beetle, Hitriga such as the white-faced starfish, Hirosukoga such as the moth and the common moth, etc., Hemiptera pests (for example, peach moa) Aphids such as aphids, cotton aphids, leafhoppers such as brown planthoppers, leafhoppers, white planthoppers, leafhoppers such as leafhoppers, red beetles, red beetles, chabaeokamushimushi, minamiokakamushi, horned beetles Whiteflies, stag beetles, scale insects such as stag beetles, staghorn beetles, pheasants, etc.), Coleopterous pests (for example, weeviles such as maizewevil, rice weevil, azuki beetle, and white-tailed beetles) Scarabaeidae, Scarabaeidae, Scarabae, etc., Beetle leaf beetle, cucumber potato beetle, Colorado potato beetle, Western corn rootworm, Southern cornle Worms such as worms, rice beetles, blue-spotted beetles, sinkworms, epilacunas such as Aedes aegypti, beetles, etc., ticks (for example, spider mites, spider mites, red spider mites, apple spider mites, oligonicas sp.), Tomatoes Flies mites such as rust mites, citrus mites, chano mites, dust mites such as chano mites, mites, etc., hymenoptera pests (eg, wasps such as wasps), straight insects (eg, grasshoppers), twins Lepidopterous pests (for example, houseflies, mosquitoes, anopheles, chironomids, black flies, mosquito flies, sand flies, sand flies, leguminous flies, tomato clover flies, leaf flies such as eggplant flies, fruit flies, fruit flies, flies Duck, butterflies, flyfish, flies, sand flies, etc.), thrips pests (for example, Thrips thrips, Thrips thrips, Thrips thrips, Thrips thrips, Thrips thrips, Thrips thrips) Nematodes (for example, root-knot nematodes, nectar nematodes, cyst nematodes, aferenchoides such as rice scented nematodes, pine wood nematodes, etc.). Preferred are Hemiptera and Thripidae pests.
本発明化合物であるPF1364を、農園芸用殺菌剤の有効成分として用いる場合は、そのまま用いても良いが、通常は適当な固体担体、液体担体、ガス状担体、界面活性剤、分散剤その他の製剤用補助剤と混合して乳剤、液剤、懸濁剤、水和剤、粉剤、粒剤、錠剤、油剤、エアゾール、フロワブル剤等の任意の剤型にして使用する。 When the compound PF1364 of the present invention is used as an active ingredient of an agricultural and horticultural fungicide, it may be used as it is, but usually a suitable solid carrier, liquid carrier, gaseous carrier, surfactant, dispersant and other It is mixed with formulation adjuvants and used in any dosage form such as emulsion, solution, suspension, wettable powder, powder, granule, tablet, oil, aerosol, flowable and the like.
固体担体としては、例えばタルク、ベンナイト、クレー、カオリン、ケイソウ土、バーミキュライト、ホワイトカーボン、炭酸カルシウム等があげられる。 Examples of the solid carrier include talc, bennite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate and the like.
液体担体としては、例えばメタノール、ｎ−ヘキサノール、エチレングリコール等のアルコール類、アセトン、メチルエチルケトン、シクロヘキサノン等のケトン類、ｎ−ヘキサン、ケロシン、灯油等の脂肪族炭化水素類、トルエン、キシレン、メチルナフタレン等の芳香族炭化水素類、ジエチルエーテル、ジオキサン、テトラヒドロフラン等のエーテル類、酢酸エチル等のエステル類、アセトニトリル、イソブチロニトリル等のニトリル類、ジメチルホルムアミド、ジメチルアセトアミド等の酸アミド類、ダイズ油、綿実油等の植物油類、ジメチルスルホキシド、水等があげられる。また、ガス担体としてはＬＰＧ、空気、窒素、炭酸ガス、ジメチルエーテル等があげられる。 Examples of the liquid carrier include alcohols such as methanol, n-hexanol and ethylene glycol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, aliphatic hydrocarbons such as n-hexane, kerosene and kerosene, toluene, xylene and methylnaphthalene. Aromatic hydrocarbons such as diethyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, nitriles such as acetonitrile and isobutyronitrile, acid amides such as dimethylformamide and dimethylacetamide, soybean oil , Vegetable oils such as cottonseed oil, dimethyl sulfoxide, water and the like. Examples of the gas carrier include LPG, air, nitrogen, carbon dioxide gas, dimethyl ether and the like.
乳化、分散、展着等のための界面活性剤、分散剤としては、例えばアルキル硫酸エステル類、アルキル（アリール）スルホン酸塩類、ポリオキシアルキレンアルキル（アリール）エーテル類、多価アルコールエステル類、リグニンスルホン酸塩等が用いられる。
更に、製剤の性状を改善するための補助剤としては、例えばカルボキシメチルセルロース、アラビアガム、ポリエチレングリコール、ステアリン酸カルシウム等が用いられる。
上記の担体、界面活性剤、分散剤、及び補助剤は、必要に応じて各々単独で、あるいは組み合わせて用いられる。
これらの製剤中の有効成分の含有量は、乳剤で通常１−７５重量％、粉剤では通常０．３−２５重量％、水和剤では通常１−９０重量％、粒剤では通常０．５−１０重量％が適当である。Surfactants and dispersants for emulsification, dispersion, spreading, etc. include, for example, alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters, lignin A sulfonate or the like is used.
Furthermore, as an auxiliary agent for improving the properties of the preparation, for example, carboxymethyl cellulose, gum arabic, polyethylene glycol, calcium stearate and the like are used.
The above carriers, surfactants, dispersants, and adjuvants may be used alone or in combination as necessary.
The content of the active ingredient in these preparations is usually 1-75% by weight for emulsions, usually 0.3-25% by weight for powders, 1-90% by weight for wettable powders, and usually 0.5% for granules. -10% by weight is suitable.
これらの製剤は、そのまま用いても良いが、場合によっては希釈して用いる。また、これらの製剤は他の殺菌剤、殺虫剤、殺ダニ剤、除草剤、植物成長調節剤、肥料等と混合して用いることもできる。 These preparations may be used as they are, but may be diluted in some cases. These preparations can also be used by mixing with other fungicides, insecticides, acaricides, herbicides, plant growth regulators, fertilizers and the like.
本明細書において、混合可能な他の有害生物防除剤とは、殺虫剤、殺菌剤、殺ダニ剤、除草剤、植物成長調節剤であり、具体的な薬剤としては、例えば、ペスティサイド マニュアル（The Pesticide Manual、第１３版 The British Crop Protection Council 発行）およびシブヤインデックス（SHIBUYA INDEX 第１０版、２００５年、SHIBUYA INDEX RESEARCH GROUP 発行）に記載のものが挙げられる。 In the present specification, other pesticides that can be mixed include insecticides, fungicides, acaricides, herbicides, plant growth regulators, and specific agents include, for example, the Pesticide Manual (The Pesticide Manual, 13th edition published by The British Crop Protection Council) and Shibuya Index (SHIBUYA INDEX 10th edition, 2005, published by SHIBUYA INDEX RESEARCH GROUP).
混合可能な他の有害生物防除剤の望ましい例としては、殺虫剤では、アセフェート（acephate）、ジクロルボス（dichlorvos）、EPN、フェニトロチオン（fenitothion）、フェナミホス（fenamifos）、プロチオホス（prothiofos）、プロフェノホス（profenofos）、ピラクロホス（pyraclofos）、クロルピリホスメチル（chlorpyrifos-methyl）、クロルフェンビンホス(chlorfenvinphos)、デメトン(demeton)、エチオン(ethion)、マラチオン(malathion)、クマホス(coumaphos)、イソキサチオン(isoxathion)、フェンチオン(fenthion)、ダイアジノン（diazinon）、チオジカルブ（thiodicarb）、アルジカルブ（aldicarb）、オキサミル（oxamyl）、プロポキスル（propoxur）、カルバリル(carbaryl)、フェノブカルブ(fenobucarb)、エチオフェンカルブ(ethiofencarb)、フェノチオカルブ(fenothiocarb)、ピリミカーブ(pirimicarb)、カルボフラン(carbofuran)、カルボスルファン(carbosulfan)、フラチオカルブ(furathiocarb)、ヒキンカルブ（hyquincarb）、アラニカルブ(alanycarb)、メソミル(methomyl)、ベンフラカルブ(benfuracarb)、カルタップ(cartap)、チオシクラム(thiocyclam)、ベンスルタップ(bensultap)、ジコホル(dicofol)、テトラジホン(tetradifon)、アクリナトリン(acrinathrin)、ビフェントリン(bifenthrin)、シクロプロトリン(cycloprothrin)、シフルトリン(cyfluthrin)、ジメフルトリン(dimefluthrin)、エンペントリン(empenthrin)、フェンフルトリン(fenfluthrin)、フェンプロパトリン(fenpropathrin)、イミプロトリン(imiprothrin)、メトフルトリン(metofluthrin)、ペルメトリン(permethrin)、フェノトリン(phenothrin)、レスメトリン(resmethrin)、テフルトリン(tefluthrin)、テトラメトリン(tetramethrin)、トラロメトリン(tralomethrin)、トランスフルトリン(transfluthrin)、シペルメトリン(cypermethrin)、デルタメトリン(deltamethrin)、シハロトリン(cyhalothrin)、フェンバレレート(fenvalerate)、フルバリネート(fluvalinate)、エトフェンプロックス(ethofenprox)、フルフェンプロックス(flufenprox)、ハルフェンプロックス(halfenprox)、シラフルオフェン(silafluofen)、シロマジン(cyromazine)、ジフルベンズロン(diflubenzuron)、テフルベンズロン(teflubenzuron)、フルシクロクスロン(flucycloxuron)、フルフェノクスロン(flufenoxuron)、ヘキサフルムロン(hexaflumuron)、ルフェヌロン(lufenuron)、ノバルロン(novaluron)、ペンフルロン(penfluron)、トリフルムロン(triflumuron)、クロルフルアズロン(chlorfluazuron)、ジアフェンチウロン(diafenthiuron)、メトプレン(methoprene)、フェノキシカルブ(fenoxycarb)、ピリプロキシフェン(pyriproxyfen)、ハロフェノジド(halofenozide)、テブフェノジド(tebufenozide)、メトキシフェノジド(methoxyfenozide)、クロマフェノジド(chromafenozide)、ジシクラニル(dicyclanil)、ブプロフェジン（buprofezin）、ヘキシチアゾクス（hexythiazox）、アミトラズ（amitraz）、クロルジメホルム（chlordimeform）、ピリダベン（pyridaben）、フェンピロキシメート（fenpyroxymate）、フルフェネリム(flufenerim)、ピリミジフェン（pyrimidifen）、テブフェンピラド（tebufenpyrad）、トルフェンピラド(tolfenpyrad)、フルアクリピリム（fluacrypyrim）、アセキノシル(acequinocyl)、シフルメトフェン（cyflumetofen）、フルベンジアミド（flubendiamide）、エチプロール（ethiprole）、フィプロニル（fipronil）、エトキサゾール（ethoxazole）、イミダクロプリド（imidacloprid）、ニテンピラム(nitenpyram)、クロチアニジン（c1othianidin）、アセタミプリド(acetamiprid)、ジノテフラン(dinotefuran)、チアクロプリド(thiacloprid)、チアメトキサム(thiamethoxam)、ピメトロジン（pymetrozine）、ビフェナゼート（bifenazate）、スピロジクロフェン（spirodiclofen）、スピロメシフェン（spiromesifen）、フロニカミド（flonicamid）、クロルフェナピル（chlorfenapyr）、ピリプロキシフェン（pyriproxyfene）、インドキサカルブ（indoxacarb）、ピリダリル（pyridalyl）、スピノサド（spinosad）、アベルメクチン（avermectin）、ミルベマイシン（milbemycin）、アザジラクチン(azadirachtin)、ニコチン(nicotine)、ロテノン(rotenone)、BT剤、昆虫病原ウイルス剤、エマメクチン安息香酸塩（emamectinbenzoate）、スピネトラム（spinetoram）、ピリフルキナゾン（pyrifluquinazon）、クロルアントラニリプロール（chlorantraniliprole）、シエノピラフェン（cyenopyrafen）、スピロテトラマット（spirotetramat）、レピメクチン（lepimectin）、メタフルミゾン（metaflumizone）、ピラフルプロール（pyrafluprole）、ピリプロール（pyriprole）、ジメフルスリン（dimefluthrin）、フェナザフロル(fenazaflor)、ヒドラメチルノン(hydramethylnon)、トリアザメート(triazamate)である。 Desirable examples of other pesticides that can be mixed include pesticides: acephate, dichlorvos, EPN, fenitrothion, fenamifos, prothiofos, profenofos , Pyraclofos, chlorpyrifos-methyl, chlorfenvinphos, demeton, ethion, malathion, coumaphos, isoxathion, fenthion ), Diazinon, thiodicarb, aldicarb, oxamyl, propoxur, carbaryl, fenobucarb, ethiofencarb, fenothiocarb, pirimicurve pirimi ) Carbofuran, carbosulfan, furathiocarb, hyquincarb, alanycarb, metomyl, benfuracarb, cartap, thiocyclam, bensultap ), Dicofol, tetradifon, acrinathrin, bifenthrin, cycloprothrin, cyfluthrin, dimefluthrin, empenthrin, fenthrin (fenthrin) , Fenpropathrin, imiprothrin, methfluthrin, permethrin, phenothrin, resmethrin, tefluthrin, tetramethrin, tramethrin, tramethrin, tramethrin Phosphorus (transfluthrin), cypermethrin (cypermethrin), deltamethrin (deltamethrin), cyhalothrin, fenvalerate, fluvalinate, etofenprox, flufenprox, halfenprox (halfenprox), silafluofen, cyromazine, diflubenzuron, teflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, lufenuron (lu) , Novaluron, penfluron, triflumuron, chlorfluazuron, diafenthiuron, metoprene, fenoxycarb, pyriproxyfen, Halofenozide , Tebufenozide, methoxyfenozide, chromafenozide, dicyclanil, buprofezin, hexythiazox, amitraz, chlordimeform, chlordimeform , Flufenerim, pyrimidifen, tebufenpyrad, tolfenpyrad, fluacrypyrim, acequinocyl, cyflumetofen, flubendiamide, flubendiamide, flubendiamide, flubendiamide ), Etoxazole, imidacloprid, nitenpyram, c1othianidin, acetamiprid (aceta) miprid), dinotefuran, thiacloprid, thiamethoxam, pymetrozine, bifenazate, spirodiclofen, spirodisifen, fenomeyr, flonicamid, flonicamid, flonicamid ), Pyriproxyfene, indoxacarb, pyridalyl, spinosad, avermectin, albamectin, milbemycin, azadirachtin, nicotine, rotenone , BT agents, entomopathogenic virus agents, emamectin benzoate, spinetoram, pyrifluquinazon, chlorantraniliprole, cyenopyrafen, spinopyrafen Tetramat, lepimectin, metaflumizone, pyrafluprole, pyriprole, dimefluthrin, fenazaflor, hydramethylnon, triazamate is there.
混合可能な殺菌剤の例としては、例えば、アゾキシストルビン(azoxystrobin)、クレソキシムメチル(kresoxym-methyl)、トリフロキシストロビン(trifloxystrobin)、オリザストロビン(orysastrobin)、ピコキシストロビン（picoxystrobin）、フロキサストロビン(fuoxastrobin)などのストロビルリン系化合物、メパニピリム（mepanipyrim）、ピリメサニル(pyrimethanil)、シプロジニル(cyprodinil)のようなアニリノピリミジン系化合物、トリアジメホン(triadimefon)、ビテルタノール(bitertanol)、トリフルミゾール(triflumizole)、エタコナゾール(etaconazole)、プロピコナゾール(propiconazole)、ペンコナゾール(penconazole)、フルシラゾール(flusilazole)、ミクロブタニル(myclobutanil)、シプロコナゾール(cyproconazole)、テブコナゾール(tebuconazole)、ヘキサコナゾール(hexaconazole)、プロクロラズ(prochloraz)、シメコナゾール(simeconazole)のようなアゾール系化合物、キノメチオネート(quinomethionate)のようなキノキサリン系化合物、マンネブ(maneb)、ジネブ(zineb)、マンコゼブ(mancozeb)、ポリカーバメート(polycarbamate)、プロビネブ(propineb)のようなジチオカーバメート系化合物、ジエトフェンカルブ(diethofencarb)のようなフェニルカーバメート系化合物、クロロタロニル(chlorothalonil)、キントゼン(quintozene)のような有機塩素系化合物、ベノミル(benomyl)、チオファネートメチル(thiophanate-methyl)、カーベンダジム(carbendazole)のようなベンズイミダゾール系化合物メタラキシル(metalaxyl)、オキサジキシル(oxadixyl)、オフラセ(ofurase)、ベナラキシル(benalaxyl)、フララキシル(furalaxyl)、シプロフラン(cyprofuram)のようなフェニルアミド系化合物、ジクロフルアニド(dichlofluanid)のようなスルフェン酸系化合物、水酸化第二銅(copperhydroxide)、オキシキノリン銅(oxine-copper)のような銅系化合物、ヒドロキシイソキサゾール(hydroxyisoxazole)のようなイソキサゾール系化合物、ホセチルアルミニウム(fosetyl-aluminium)、トルクロホス−メチル(tolclofos-methyl)のような有機リン系化合物、キャプタン(captan)、カプタホール(captafol)、フォルペット(folpet)のようなＮ−ハロゲノチオアルキル系化合物、プロシミドン(procymidone)、イプロジオン(iprodione)、ビンクロゾリン(vinchlozolin)のようなジカルボキシイミド系化合物、フルトラニル(flutolanil)、メプロニル(mepronil)のようなベンズアニリド系化合物、フェンプロピモルフ(fenpropimorph)、ジメトモルフ(dimethomorph)のようなモルフォリン系化合物、水酸化トリフェニルスズ(fenthinhydroxide)、酢酸トリフェニルスズ(fenthin acetate)のような有機スズ系化合物、フルジオキソニル(fludioxonil)、フェンピクロニル(fenpiclonil)のようなシアノピロール系化合物、その他フサライド(fthalide)、プロベナゾール(probenazole)、アシベンゾラルSメチル(acibenzolar-S-methyl)、チアジニル(tiadinil)、イソチアニル(isotianil)、カルプロパミド(carpropamid)、ジクロシメット(diclocymet)、フェノキサニル(fenoxanil)、トリシクラゾール(tricyclazole)、ピロキロン(pyroquilon)、フェリムゾン(ferimzone)、フルアジナム(fluazinam)、シモキサニル(cymoxanil)、トリホリン(triforine)、ピリフェノックス(pyrifenox)、フェナリモル(fenarimol)、フェンプロピディン(fenpropidin)、ペンシクロン(pencycuron)、シアゾファミド(cyazofamid)、シフルフェナミド(cyflufenamid)、ボスカリド(boscalid)、ペンチオピラド(penthiopyrad)、プロキナジド（proquinazid）、キノキシフェン(quinoxyfen)、ファモキサドン(famoxadone)、フェナミドン(fenamidone)、イプロバリカルブ(iprovalicarb)、ベンチアバリカルブイソプロピル(benthiavalicarb-isopropyl)、フルオピコリド(fluopicolide)、ピリベンカルブ(pyribencarb)、カスガマイシン(kasugamycin)、またはバリダマイシン(validamycin)が挙げられる。
Examples of mixable fungicides include, for example, azoxystrobin, kresoxym-methyl, trifloxystrobin, orysastrobin, picoxystrobin, Strobilurin compounds such as floxastrobin, mepanipyrim, pyrimethanil, anilinopyrimidine compounds such as cyprodinil, triadimefon, bitertanol, triflumizole ( triflumizole), etaconazole, etaconazole, propiconazole, penconazole, flusilazole, microbutanil, cyproconazole, tebuconazole, hexaconazole, proclorazol (prochloraz), shime Azole compounds such as simeconazole, quinoxaline compounds such as quinomethionate, maneb, zineb, mancozeb, polycarbamate, propineb, etc. Dithiocarbamate compounds, phenylcarbamate compounds such as diethofencarb, chlorothalonil, organochlorine compounds such as quintozene, benomyl, thiophanate-methyl, carbendazole Benzimidazole compounds such as metalaxyl, oxadixyl, ofurase, benalaxyl, furalaxyl, phenylamides such as cyprofuram, dichlofluanid Like sul Phenic acid compound, copper hydroxide (copperhydroxide), copper compound such as oxine-copper, isoxazole compound such as hydroxyisoxazole, fosetyl-aluminium , Organophosphorus compounds such as tolclofos-methyl, captan, captafol, N-halogenothioalkyl compounds such as folpet, procymidone, iprodione ( iprodione), dicarboximide compounds such as vinchlozolin, flutolanil, benzanilide compounds such as mepronil, morpholine compounds such as fenpropimorph, dimethomorph , Triphenyltin hydroxide, fenthin acetate Organotin compounds such as ate), cyanopyrrole compounds such as fludioxonil, fenpiclonil, other fthalide, probenazole, acibenzolar-S-methyl, thiazinyl (tiadinil), isotianil, carpropamid, diclocymet, phenoxanil, tricyclazole, pyroquilon, ferimzone, fluazinam, fluazinam, cymoxanil (triforine), pyrifenox, fenarimol, fenpropidin, pencicuron, cyazofamid, cyflufenamid, boscalid, penthiopyrad (prothiodrad) proquinazid), mushroom Fen (quinoxyfen), famoxadone, fenamidon (fenamidone), iprovalicarb, iventalicarb, benthiavalicarb-isopropyl, fluopicolide, pyribencarb, kasugamycin val, myida ).
以下、実施例を挙げて本発明を具体的に説明するが、本発明はこれらの実施例に限定されるものではない。 EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated concretely, this invention is not limited to these Examples.
製造例
製造例１ PF1364の製造
種培地として、でんぷん（スターチ）２．０％、ぶどう糖（グルコース）１．０％、ポリペプトン０．５％、小麦胚芽 ０．６％、酵母エキス ０．３％、大豆粕 ０．２％および炭酸カルシウム ０．２％ の組成からなる培地（殺菌前ｐＨ７．０）を用いた。また、生産培地としては、充分水を吸収させた米に、大豆粕０．３％を加えたものを用いた。
前記の種培地２０ｍＬを分注した１００ｍＬ容三角フラスコを１２０℃で２０分間殺菌し、これにPF1364株の斜面寒天培養の１白金耳を接種後、２５℃で３日間振とう培養することによって種培養液を得た。次いで、生産培地（米）４ｋｇずつを仕込んだ３１５×４３５×９８ｍｍの培養容器（ステンレス鋼製）を１２０℃で２０分間殺菌し、これに上記種培養液を１５０ｍＬずつ接種し、よく撹拌後、２５℃で１４日間静置培養した。
こうして得られた培養物１ｋｇに６７％アセトン水溶液を等量加えて目的物質を抽出しアセトンを減圧下留去し酢酸エチルを加えて抽出した。酢酸エチル層を減圧濃縮して１．０３ｇの粗抽出物を得た。これをＨＰ−２０のカラムにかけて８０％アセトン溶離部で活性成分を溶離し減圧下乾燥して２１０ｍｇの固形物を得た。この固形物を少量のメタノールに溶離後、ＴＬＣまたは高速液体クロマトグラフィー（CAPCELPAK・ODS（SHISEIDO）４．６φ×２００ｍｍ、水-アセトニトリル）にて分画操作を行うことにより、式（１）で示すPF1364を単離することが出来る。Production Example Production Example 1 Production of PF1364 As a seed medium, starch (starch) 2.0%, glucose (glucose) 1.0%, polypeptone 0.5%, wheat germ 0.6%, yeast extract 0.3%, A medium (pH 7.0 before sterilization) having a composition of 0.2% soybean meal and 0.2% calcium carbonate was used. Moreover, as a production medium, what added 0.3% of soybean meal to the rice which absorbed water enough was used.
The 100 mL Erlenmeyer flask into which 20 mL of the above seed medium was dispensed was sterilized at 120 ° C. for 20 minutes, and after inoculating one platinum loop of slant agar culture of PF1364 strain, the seed was cultured by shaking at 25 ° C. for 3 days. A culture broth was obtained. Next, a 315 × 435 × 98 mm culture vessel (made of stainless steel) charged with 4 kg of production medium (rice) was sterilized at 120 ° C. for 20 minutes, inoculated with 150 mL of the seed culture solution, and stirred well. Static culture was performed at 25 ° C. for 14 days.
An equivalent amount of 67% acetone aqueous solution was added to 1 kg of the thus obtained culture to extract the target substance, acetone was distilled off under reduced pressure, and ethyl acetate was added for extraction. The ethyl acetate layer was concentrated under reduced pressure to obtain 1.03 g of a crude extract. This was applied to a column of HP-20 and the active ingredient was eluted with an 80% acetone eluent and dried under reduced pressure to obtain 210 mg of a solid. This solid is eluted with a small amount of methanol, and then subjected to fractionation operation by TLC or high performance liquid chromatography (CAPCELPAK • ODS (SHISEIDO) 4.6φ × 200 mm, water-acetonitrile), thereby obtaining the formula (1). PF1364 can be isolated.
製剤例
製剤例１〔粒剤〕
PF1364 ３重量％
ベントナイト ４０重量％
タルク １０重量％
クレー ４５重量％
リグニンスルホン酸カルシウム ２重量％
上記成分を均一に粉砕混合し、水を加えてよく練合した後、造粒乾燥して粒剤を得た。Formulation Example Formulation Example 1 [Granule]
PF1364 3% by weight
Bentonite 40% by weight
Talc 10% by weight
45% by weight clay
2% by weight calcium lignin sulfonate
The above components were pulverized and mixed uniformly, kneaded well with water, and granulated and dried to obtain granules.
製剤例２〔水和剤〕
PF1364 ３０重量％
クレー ５０重量％
ホワイトカーボン ２重量％
ケイソウ土 １３重量％
リグニンスルホン酸カルシウム ４重量％
ラウリル硫酸ナトリウム １重量％
上記成分を均一に混合し、粉砕して水和剤を得た。Formulation Example 2 [wettable powder]
PF1364 30% by weight
50% by weight of clay
2% white carbon
Diatomaceous earth 13% by weight
Calcium lignin sulfonate 4% by weight
Sodium lauryl sulfate 1% by weight
The above ingredients were mixed uniformly and pulverized to obtain a wettable powder.
製剤例３〔顆粒水和剤〕
PF1364 ３０重量％
クレー ６０重量％
デキストリン ５重量％
アルキルマレイン酸共重合物 ４重量％
ラウリル硫酸ナトリウム １重量％
上記成分を均一に粉砕混合し、水を加えてよく練合した後、造粒乾燥して顆粒水和剤を得たFormulation Example 3 [Granule wettable powder]
PF1364 30% by weight
60% clay
Dextrin 5% by weight
Alkyl maleic acid copolymer 4% by weight
Sodium lauryl sulfate 1% by weight
The above ingredients were uniformly pulverized and mixed, mixed well with water, then granulated and dried to obtain a granulated wettable powder
製剤例４〔フロアブル剤〕
PF1364 ２５重量％
ＰＯＥポリスチリルフェニルエーテル硫酸塩 ５重量％
プロピレングリコール ６重量％
ベントナイト １重量％
キサンタンガム１％水溶液 ３重量％
ＰＲＯＮＡＬ ＥＸ−３００（東邦化学工業株式会社）０．０５重量％
ＡＤＤＡＣ ８２７（ケイ・アイ化成株式会社） ０．０２重量％
水 加えて１００重量％
上記配合からキサンタンガム１％水溶液と適当量の水を除いた全量を予備混合した後、湿式粉砕機にて粉砕した。その後、キサンタンガム１％水溶液と残りの水を加え１００重量％としてフロアブル剤を得た。Formulation Example 4 [Flowable Agent]
PF1364 25% by weight
POE polystyryl phenyl ether sulfate 5% by weight
Propylene glycol 6% by weight
Bentonite 1% by weight
Xanthan gum 1% aqueous solution 3% by weight
PRONAL EX-300 (Toho Chemical Co., Ltd.) 0.05% by weight
ADDAC 827 (Kay Kasei Co., Ltd.) 0.02% by weight
100% by weight of water
The total amount excluding the 1% aqueous solution of xanthan gum and an appropriate amount of water from the above blend was premixed and then pulverized with a wet pulverizer. Thereafter, 1% aqueous solution of xanthan gum and the remaining water were added to obtain a flowable agent at 100% by weight.
製剤例５〔乳剤〕
PF1364 １５重量％
Ｎ，Ｎ−ジメチルホルムアミド ２０重量％
ソルベッソ１５０（エクソンモービル有限会社） ５５重量％
ポリオキシエチレンアルキルアリールエーテル １０重量％
上記成分を均一に混合、溶解して乳剤を得た。Formulation Example 5 [Emulsion]
PF1364 15% by weight
N, N-dimethylformamide 20% by weight
Solvesso 150 (ExxonMobil Co., Ltd.) 55% by weight
10% by weight of polyoxyethylene alkyl aryl ether
The above ingredients were uniformly mixed and dissolved to obtain an emulsion.
製剤例６〔粉剤〕
PF1364 ２重量％
クレー ６０重量％
タルク ３７重量％
ステアリン酸カルシウム １重量％
上記成分を均一に混合して粉剤を得た。Formulation Example 6 [powder]
PF1364 2% by weight
60% clay
Talc 37% by weight
Calcium stearate 1% by weight
The said component was mixed uniformly and the powder agent was obtained.
製剤例７〔ＤＬ粉剤〕
PF1364 ２重量％
ＤＬクレー ９４．５重量％
ホワイトカーボン ２重量％
ステアリン酸カルシウム １重量％
軽質流動パラフィン ０．５重量％
上記成分を均一に混合して粉剤を得た。Formulation Example 7 [DL powder]
PF1364 2% by weight
DL clay 94.5% by weight
2% white carbon
Calcium stearate 1% by weight
Light liquid paraffin 0.5% by weight
The said component was mixed uniformly and the powder agent was obtained.
製剤例８〔微粒剤Ｆ〕
PF1364 ２重量％
キャリヤー ９４重量％
ホワイトカーボン ２重量％
ハイゾールＳＡＳ−２９６ ２重量％
上記成分を均一に混合して粉剤を得た。Formulation Example 8 [Fine Granule F]
PF1364 2% by weight
Carrier 94% by weight
2% white carbon
Hyzol SAS-296 2% by weight
The said component was mixed uniformly and the powder agent was obtained.
試験例
試験例１ ヒメトビウンカ防除試験
水耕栽培のコムギ苗根部に、１０％アセトン水にて所定濃度に調製した薬液を処理した（１０μｇ/苗）。３日間根部より薬剤を吸収させた後、これにヒメトビウンカ２令幼虫を１０頭放飼した。その後、２５℃の恒温室（１６時間明期一８時間暗期）に放置した。放飼３日後に虫の生死を観察し、次式に従って死虫率を算出した。２連制試験。
死虫率（％）＝{死亡虫数 ／（生存虫数十死亡虫数）}×１００
表１に示すように、PF1364の殺虫活性は、Austin類縁のDehydroaustinと比べて、極めて高いことが明らかである。
Test example Test example 1 Japanese black leafhopper control test Hydroponic wheat seedling roots were treated with a chemical solution prepared to a predetermined concentration with 10% acetone water (10 μg / seedling). After the drug was absorbed from the root for 3 days, 10 second-instar larvae were released. Thereafter, it was left in a constant temperature room at 25 ° C. (16 hours light period 18 hours dark period). The insects were observed for life and death 3 days after the release, and the death rate was calculated according to the following formula. Two-run test.
Mortality rate (%) = {Number of dead insects / (Number of living insects tens of dead insects)} x 100
As shown in Table 1, it is clear that the insecticidal activity of PF1364 is extremely high compared to Austin-related Dehydroaustin.
試験例２ アカヒゲホソミドリカスミカメ防除試験
ポット栽培のイネ苗に、１０％アセトン水にて２００ｐｐｍとなるように調製した薬液を茎葉散布処理した。風乾後、これに２令幼虫を放飼した。その後、２５℃の恒温室（１６時間明期一８時間暗期）に放置した。放飼３日後に虫の生死を観察し、次式に従って死虫率を算出した。２連制試験。
死虫率（％）＝{死亡虫数 ／（生存虫数十死亡虫数）}×１００
PF1364は、アカヒゲホソミドリカスミカメに対して、死虫率８０％以上の高い殺虫活性を示した。
Test Example 2 Akahigehosomidorikasikameka control test A potted rice seedling was sprayed with a chemical solution prepared to 200 ppm in 10% acetone water. After air drying, the 2nd instar larvae were released. Thereafter, it was left in a constant temperature room at 25 ° C. (16 hours light period 18 hours dark period). The insects were observed for life and death 3 days after the release, and the death rate was calculated according to the following formula. Two-run test.
Mortality rate (%) = {Number of dead insects / (Number of living insects tens of dead insects)} x 100
PF1364 showed a high insecticidal activity with a mortality rate of 80% or more against the red beetle.
試験例３ ワタアブラムシ防除試験
ポット栽培のキュウリから直径２．０ｃｍのリーフディスクを切り抜き、これに５０％アセトン水（０．０５％Tween２０加用）にて２００ｐｐｍとなるように調製した薬液を散布した。風乾後、これに１令幼虫を放飼した。その後、これを２５℃の恒温室（１６時間明期一８時間暗期）に放置した。放飼３日後に虫の生死を観察し、次式に従って死虫率を算出した。２連制試験。
死虫率（％）＝{死亡虫数 ／（生存虫数十死亡虫数）}×１００
PF1364は、ワタアブラムシに対して、死虫率８０％以上の高い殺虫活性を示した。
Test Example 3 Cotton Aphid Control Test A leaf disc having a diameter of 2.0 cm was cut out from a pot-grown cucumber and sprayed with a chemical solution adjusted to 200 ppm with 50% acetone water (added with 0.05% Tween 20). . After air drying, the first instar larvae were released. Thereafter, this was left in a constant temperature room at 25 ° C. (16 hours light period 18 hours dark period). The insects were observed for life and death 3 days after the release, and the death rate was calculated according to the following formula. Two-run test.
Mortality rate (%) = {Number of dead insects / (Number of living insects tens of dead insects)} x 100
PF1364 showed high insecticidal activity against cotton aphids with a mortality rate of 80% or more.
試験例４ ミカンキイロアザミウマ防除試験
ポット栽培のインゲンから直径２．８ｃｍのリーフディスクを切り抜き、これに５０％アセトン水（０．０５％Tween２０加用）にて２００ｐｐｍとなるように調製した薬液を散布した。風乾後、これに１令幼虫を放飼した。その後、これを２５℃の恒温室（１６時間明期一８時間暗期）に放置した。放飼３日後に虫の生死を観察し、次式に従って死虫率を算出した。２連制試験。
死虫率（％）＝{死亡虫数 ／（生存虫数十死亡虫数）}×１００
PF1364は、ミカンキイロアザミウマに対して、死虫率８０％以上の高い殺虫活性を示した。Test example 4 Citrus thrips control test A leaf disk with a diameter of 2.8 cm was cut out from a pot-grown bean and sprayed with a chemical solution adjusted to 200 ppm with 50% acetone water (added with 0.05% Tween 20). did. After air drying, the first instar larvae were released. Thereafter, this was left in a constant temperature room at 25 ° C. (16 hours light period 18 hours dark period). The insects were observed for life and death 3 days after the release, and the death rate was calculated according to the following formula. Two-run test.
Mortality rate (%) = {Number of dead insects / (Number of living insects tens of dead insects)} x 100
PF1364 showed a high insecticidal activity with a mortality rate of 80% or more against the orange thrips.
試験例５ ツマグロヨコバイ防除試験
ポット栽培のイネ苗に、１０％アセトン水にて２００ｐｐｍとなるように調製した薬液を茎葉散布処理した。風乾後、これに２令幼虫を放飼した。その後、２５℃の恒温室（１６時間明期一８時間暗期）に放置した。放飼３日後に虫の生死を観察し、次式に従って死虫率を算出した。２連制試験。
死虫率（％）＝{死亡虫数 ／（生存虫数十死亡虫数）}×１００
PF1364は、ツマグロヨコバイに対して、死虫率８０％以上の高い殺虫活性を示した。
Test Example 5 Leafhopper control test A potted rice seedling was sprayed with a chemical solution prepared to 200 ppm with 10% acetone water. After air drying, the 2nd instar larvae were released. Thereafter, it was left in a constant temperature room at 25 ° C. (16 hours light period 18 hours dark period). The insects were observed for life and death 3 days after the release, and the death rate was calculated according to the following formula. Two-run test.
Mortality rate (%) = {Number of dead insects / (Number of living insects tens of dead insects)} x 100
PF1364 showed a high insecticidal activity with a mortality rate of 80% or more against the leafhopper leafhopper.
試験例６ オンシツコナジラミ防除試験
ポット栽培のキュウリに、５０％アセトン水（０．０５％Tween２０加用）にて１００ｐｐｍとなるように調製した薬液を散布した。これにオンシツコナジラミ成虫を１０頭（／１株）ずつ放飼し、２日間産卵させた。放飼２日後、成虫を除き、ポットを２５℃の恒温室（１６時間明期一８時間暗期）に放置した。成虫放飼１５日後に中老令幼虫数を観察し、次式に従って密度指数を算出した。
密度指数＝（処理区の中老令幼虫数 ／ 無処理区の中老令幼虫数）×１００
PF1364は、オンシツコナジラミに対して、密度指数０の高い密度抑制効果を示した。Test Example 6 Onsite whitefly control test A potted cucumber was sprayed with a chemical solution prepared to 100 ppm with 50% acetone water (added with 0.05% Tween 20). To this, 10 adults (one strain) of the whitefly whitefly were released and allowed to lay eggs for 2 days. Two days after release, the adults were removed and the pots were left in a constant temperature room at 25 ° C. (16 hours light period, 18 hours dark period). The number of middle-aged larvae was observed 15 days after adult release, and the density index was calculated according to the following formula.
Density index = (number of middle-aged larvae in treated area / number of middle-aged larvae in untreated area) x 100
PF1364 showed a high density suppression effect with a density index of 0 against white fly whitefly.
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008182390AJP5268461B2 (en) | 2008-07-14 | 2008-07-14 | PF1364 substance, its production method, production strain, and agricultural and horticultural insecticide containing the same as an active ingredient |
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008182390AJP5268461B2 (en) | 2008-07-14 | 2008-07-14 | PF1364 substance, its production method, production strain, and agricultural and horticultural insecticide containing the same as an active ingredient |
| Publication Number | Publication Date |
|---|---|
| JP2010018586A JP2010018586A (en) | 2010-01-28 |
| JP5268461B2true JP5268461B2 (en) | 2013-08-21 |
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008182390AExpired - Fee RelatedJP5268461B2 (en) | 2008-07-14 | 2008-07-14 | PF1364 substance, its production method, production strain, and agricultural and horticultural insecticide containing the same as an active ingredient |
| Country | Link |
|---|---|
| JP (1) | JP5268461B2 (en) |
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