CN112930339B - (杂)芳基咪唑化合物及有害生物防除剂 - Google Patents
(杂)芳基咪唑化合物及有害生物防除剂 Download PDFInfo
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- CN112930339B CN112930339B CN201980071304.8A CN201980071304A CN112930339B CN 112930339 B CN112930339 B CN 112930339B CN 201980071304 A CN201980071304 A CN 201980071304A CN 112930339 B CN112930339 B CN 112930339B
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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Abstract
本发明的课题在于提供有害生物防除活性、其中尤其是杀虫活性和/或杀螨活性优异、安全性优异、并且能够在工业上有利地合成的(杂)芳基咪唑化合物。本发明的(杂)芳基咪唑化合物为式(I)所示的化合物、其N‑氧化物化合物、立体异构体、互变异构体、水合物或它们的盐。式(I)中,B1为氮原子或CH,X为取代或未取代的C3~8环烷基,R1为取代或未取代的C1~6烷基硫基、或者取代或未取代的C1~6烷基磺酰基,R2为取代或未取代的C1~6烷基,且R为取代或未取代的C2~6烯基。
Description
技术领域
本发明涉及(杂)芳基咪唑化合物及有害生物防除剂。更详细而言,本发明涉及具有优异的杀虫活性和/或杀螨活性、安全性优异且能够在工业上有利地合成的(杂)芳基咪唑化合物、以及含有该(杂)芳基咪唑化合物作为有效成分的有害生物防除剂。
本申请针对在2018年10月29日提出申请的日本专利申请第2018-202998号主张优先权,将其内容援引于本文。
背景技术
已经提出各种具有杀虫·杀螨活性的化合物。为了将这样的化合物作为农药进行实际应用,不仅要求效力充分高,而且还要求不易产生耐药性,不对植物造成药害,不引起土壤污染,对家畜、鱼类等的毒性低等。
其中,在专利文献1中公开了式(A)所示的化合物等。
[化学式1]
另外,在专利文献2中公开了式(B)所示的化合物等。
[化学式2]
现有技术文献
专利文献
专利文献1:WO2017/104741A
专利文献2:WO2016/121997A
发明内容
发明要解决的课题
本发明的课题在于提供有害生物防除活性、其中尤其是杀虫活性和/或杀螨活性优异、安全性优异、并且能够在工业上有利地合成的(杂)芳基咪唑化合物。本发明的另一课题在于提供含有(杂)芳基咪唑化合物作为有效成分的有害生物防除剂、杀虫或杀螨剂、体外寄生虫防除剂、或者体内寄生虫防除或驱除剂。此外,还提供含有(杂)芳基咪唑化合物作为有效成分的种子处理剂、营养繁殖器官处理剂、水稻育苗箱处理用农药粒状组合剂、土壤处理剂、饵剂、植物生长促进剂。
用于解决课题的手段
为了解决上述课题而进行了深入研究,结果完成了包含以下方式的本发明。
〔1〕式(I)所示的化合物、其N-氧化物化合物、立体异构体、互变异构体、水合物或它们的盐。
[化学式3]
式(I)中,
B1为氮原子或CH,
X为取代或未取代的C3~8环烷基,
R1为取代或未取代的C1~6烷基硫基、或者取代或未取代的C1~6烷基磺酰基,
R2为取代或未取代的C1~6烷基,且
R为取代或未取代的C2~6烯基。
〔2〕根据前述〔1〕所述的化合物、其N-氧化物化合物、立体异构体、互变异构体、水合物或它们的盐,其中,
式(I)为式(II)。
[化学式4]
式(II)中,
R1、R2及X表示与式(I)中的R1、R2及X同样的含义。
R3为氢原子或卤代基。
R4为C1~4卤代烷基。
式(II)中的碳-碳立体双键表示E体或Z体或者它们的混合物。
〔3〕式(III)~式(X)中的任一者所示的化合物、其N-氧化物化合物、立体异构体、互变异构体、水合物或它们的盐。
[化学式5]
[化学式6]
(式(IV)中的碳-碳立体双键表示E体或Z体或者它们的混合物。)
[化学式7]
[化学式8]
[化学式9]
(式(VII)中的碳-碳立体双键表示E体或Z体或者它们的混合物。)
[化学式10]
[化学式11]
[化学式12]
〔4〕有害生物防除剂,其含有选自由前述〔1〕~〔3〕中所述的化合物、其N-氧化物化合物、立体异构体、互变异构体、水合物及它们的盐组成的组中的至少1者作为有效成分。
〔5〕杀虫或杀螨剂,其含有选自由前述〔1〕~〔3〕中所述的化合物、其N-氧化物化合物、立体异构体、互变异构体、水合物及它们的盐组成的组中的至少1者作为有效成分。
〔6〕体外寄生虫防除剂,其含有选自由前述〔1〕~〔3〕中所述的化合物、其N-氧化物化合物、立体异构体、互变异构体、水合物及它们的盐组成的组中的至少1者作为有效成分。
〔7〕体内寄生虫防除剂或驱除剂,其含有选自由前述〔1〕~〔3〕中所述的化合物、其N-氧化物化合物、立体异构体、互变异构体、水合物及它们的盐组成的组中的至少1者作为有效成分。
〔8〕种子处理剂或营养繁殖器官处理剂,其含有选自由前述〔1〕~〔3〕中所述的化合物、其N-氧化物化合物、立体异构体、互变异构体、水合物及它们的盐组成的组中的至少1者作为有效成分。
〔9〕水稻育苗箱处理用农药粒状组合剂,其含有选自由前述〔1〕~〔3〕中所述的化合物、其N-氧化物化合物、立体异构体、互变异构体、水合物及它们的盐组成的组中的至少1者作为有效成分。
〔10〕土壤处理剂,其含有选自由前述〔1〕~〔3〕中所述的化合物、其N-氧化物化合物、立体异构体、互变异构体、水合物及它们的盐组成的组中的至少1者作为有效成分。
〔11〕饵剂,其含有选自由前述〔1〕~〔3〕中所述的化合物、其N-氧化物化合物、立体异构体、互变异构体、水合物及它们的盐组成的组中的至少1者作为有效成分。
〔12〕植物生长促进剂,其含有选自由前述〔1〕~〔3〕中所述的化合物、其N-氧化物化合物、立体异构体、互变异构体、水合物及它们的盐组成的组中的至少1者作为有效成分。
发明效果
本发明的(杂)芳基咪唑化合物能够防除在农作物、卫生方面成为问题的有害生物。尤其是能够以较低浓度有效地防除农业害虫及螨类。而且,能够有效地防除危害人畜的体外寄生虫及体内寄生虫。
另外,还能够作为种子处理剂或营养繁殖器官处理剂、水稻育苗箱处理用农药粒状组合剂、土壤处理剂、饵剂、植物生长促进剂使用。
具体实施方式
〔(杂)芳基咪唑化合物〕
本发明的(杂)芳基咪唑化合物为式(I)所示的化合物(以下有时记作化合物(I)。)、其N-氧化物化合物、立体异构体、互变异构体、水合物或它们的盐。式(I)所示的化合物包含镜像异构体或作为非对映异构体的全部的立体异构体。
[化学式13]
在本发明中,术语“未取代(unsubstituted)”是指仅为成为母核的基团。在仅记载成为母核的基团的名称而没有记载“取代”时,只要无特别说明,均是“未取代”的含义。
另一方面,术语“取代(substituted)”是指:成为母核的基团的任一氢原子被与母核相同或不同结构的基团(取代基)取代。因此,“取代基”是与成为母核的基团键合的其他基团。取代基可以为1个,也可以为2个以上。2个以上的取代基可以相同,也可以不同。
术语“C1~6”等表示成为母核的基团的碳原子数为1~6个等。该碳原子数不包括在取代基中存在的碳原子的数量。例如具有乙氧基作为取代基的丁基被分类为C2烷氧基C4烷基。
“取代基”只要为化学上所允许且具有本发明效果,则并无特别限制。以下,例示可成为“取代基”的基团。
甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、正己基等C1~6烷基;
乙烯基、1-丙烯基、2-丙烯基(烯丙基)、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基等C2~6烯基;
乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基等C2~6炔基;
环丙基、环丁基、环戊基、环己基、立方烷基(cubanyl group)等C3~8环烷基;
苯基、萘基等C6~10芳基;
苄基、苯乙基等C6~10芳基C1~6烷基;
3~6元杂环基;
3~6元杂环基C1~6烷基;
羟基;
甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基、叔丁氧基等C1~6烷氧基;
乙烯基氧基、烯丙基氧基、丙烯基氧基、丁烯基氧基等C2~6烯基氧基;
乙炔基氧基、炔丙基氧基等C2~6炔基氧基;
苯氧基、萘氧基等C6~10芳基氧基;
苄基氧基、苯乙基氧基等C6~10芳基C1~6烷氧基;
噻唑基氧基、吡啶基氧基等5~6元杂芳基氧基;
噻唑基甲基氧基、吡啶基甲基氧基等5~6元杂芳基C1~6烷基氧基;
甲酰基;
乙酰基、丙酰基等C1~6烷基羰基;
甲酰氧基;
乙酰基氧基、丙酰基氧基等C1~6烷基羰基氧基;
苯甲酰基等C6~10芳基羰基;
甲氧基羰基、乙氧基羰基、正丙氧基羰基、异丙氧基羰基、正丁氧基羰基、叔丁氧基羰基等C1~6烷氧基羰基;
甲氧基羰基氧基、乙氧基羰基氧基、正丙氧基羰基氧基、异丙氧基羰基氧基、正丁氧基羰基氧基、叔丁氧基羰基氧基等C1~6烷氧基羰基氧基;
羧基;
氟基、氯基、溴基、碘基等卤代基;
氟甲基、二氟甲基、三氟甲基、2,2,2-三氟乙基、五氟乙基、3,3,3-三氟丙基、2,2,3,3,3-五氟丙基、全氟丙基、2,2,2-三氟-1-三氟甲基乙基、全氟异丙基、4-氟丁基、2,2,3,3,4,4,4-七氟丁基、全氟丁基、全氟戊基、全氟己基、氯甲基、溴甲基、二氯甲基、二溴甲基、三氯甲基、三溴甲基、1-氯乙基、2,2,2-三氯乙基、4-氯丁基、全氯己基、2,4,6-三氯己基等C1~6卤代烷基;
2-氯-1-丙烯基、2-氟-1-丁烯基等C2~6卤代烯基;
4,4-二氯-1-丁炔基、4-氟-1-戊炔基、5-溴-2-戊炔基等C2~6卤代炔基;
三氟甲氧基、2-氯正丙氧基、2,3-二氯丁氧基、全氟丙氧基等C1~6卤代烷氧基;
2-氯丙烯基氧基、3-溴丁烯基氧基等C2~6卤代烯基氧基;
氯乙酰基、三氟乙酰基、三氯乙酰基等C1~6卤代烷基羰基;
氨基;
甲基氨基、二甲基氨基、二乙基氨基等C1~6烷基取代氨基;
苯胺基、萘基氨基等C6~10芳基氨基;
苄基氨基、苯乙基氨基等C6~10芳基C1~6烷基氨基;
甲酰氨基;
乙酰基氨基、丙酰基氨基、丁酰基氨基、异丙基羰基氨基等C1~6烷基羰基氨基;
甲氧基羰基氨基、乙氧基羰基氨基、正丙氧基羰基氨基、异丙氧基羰基氨基等C1~6烷氧基羰基氨基;
氨基羰基、二甲基氨基羰基、苯基氨基羰基、N-苯基-N-甲基氨基羰基等未取代或具有取代基的氨基羰基;
亚氨基甲基、(1-亚氨基)乙基、(1-亚氨基)正丙基等亚氨基C1~6烷基;
N-羟基-亚氨基甲基、(1-(N-羟基)-亚氨基)乙基、(1-(N-羟基)-亚氨基)丙基、N-甲氧基-亚氨基甲基、(1-(N-甲氧基)-亚氨基)乙基等取代或未取代的N-羟基亚氨基C1~6烷基;
甲氧基亚氨基、乙氧基亚氨基、正丙氧基亚氨基、异丙氧基亚氨基、正丁氧基亚氨基等C1~6烷氧基亚氨基;
氨基羰基氧基;
乙基氨基羰基氧基、二甲基氨基羰基氧基等C1~6烷基取代氨基羰基氧基;
巯基;
甲基硫基、乙基硫基、正丙基硫基、异丙基硫基、正丁基硫基、异丁基硫基、仲丁基硫基、叔丁基硫基等C1~6烷基硫基;
三氟甲基硫基、2,2,2-三氟乙基硫基等C1~6卤代烷基硫基;
苯基硫基、萘基硫基等C6~10芳基硫基;
噻唑基硫基、吡啶基硫基等5~6元杂芳基硫基;
甲基亚磺酰基、乙基亚磺酰基、叔丁基亚磺酰基等C1~6烷基亚磺酰基;
三氟甲基亚磺酰基、2,2,2-三氟乙基亚磺酰基等C1~6卤代烷基亚磺酰基;
苯基亚磺酰基等C6~10芳基亚磺酰基;
噻唑基亚磺酰基、吡啶基亚磺酰基等5~6元杂芳基亚磺酰基;
甲基磺酰基、乙基磺酰基、叔丁基磺酰基等C1~6烷基磺酰基;
三氟甲基磺酰基、2,2,2-三氟乙基磺酰基等C1~6卤代烷基磺酰基;
苯基磺酰基等C6~10芳基磺酰基;
噻唑基磺酰基、吡啶基磺酰基等5~6元杂芳基磺酰基;
甲基磺酰基氧基、乙基磺酰基氧基、叔丁基磺酰基氧基等C1~6烷基磺酰基氧基;
三氟甲基磺酰基氧基、2,2,2-三氟乙基磺酰基氧基等C1~6卤代烷基磺酰基氧基;
氨基硫羰基;
三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基等三C1~6烷基取代甲硅烷基;
三苯基甲硅烷基等三C6~10芳基取代甲硅烷基;
氰基;硝基;
另外,就这些“取代基”而言,该取代基中的任一氢原子可以被不同结构的基团取代。作为此时的“取代基”,可列举C1~6烷基、C1~6卤代烷基、C1~6烷氧基、C1~6卤代烷氧基、卤代基、氰基、硝基等。
另外,上述的“3~6元杂环基”是指包含选自由氮原子、氧原子及硫原子组成的组中的1~4个杂原子作为环的构成原子的基团。杂环基可以是单环及多环中的任一者。就多环杂环基而言,只要至少一个环为杂环,则其余的环可以是饱和脂环、不饱和脂环或芳香环中的任一者。作为“3~6元杂环基”,可列举3~6元饱和杂环基、5~6元杂芳基、5~6元部分不饱和杂环基等。
作为3~6元饱和杂环基,可列举氮丙啶基、环氧基、吡咯烷基、四氢呋喃基、噻唑烷基、哌啶基、哌嗪基、吗啉基、二氧杂环戊基、二氧杂环己基等。
作为5元杂芳基,可列举吡咯基、呋喃基、噻吩基、咪唑基、吡唑基、噁唑基、异噁唑基、噻唑基、异噻唑基、三唑基、噁二唑基、噻二唑基、四唑基等。
作为6元杂芳基,可列举吡啶基、吡嗪基、嘧啶基、哒嗪基、三嗪基等。
〔B1〕
式(I)中,B1为氮原子或CH。
即,式(I)所示的化合物为以下的式(I-1)或式(I-2)所示的化合物。
[化学式14]
[化学式15]
式(I-1)及式(I-2)中,X、R1、R2及R表示与式(I)中的X、R1、R2及R相同的含义。
B1优选为氮原子。
〔X〕
式(I)中,X为取代或未取代的C3~8环烷基。
作为X中的“C3~8环烷基”,可列举环丙基、环丁基、环戊基、环己基、立方烷基等。
作为X中的“取代C3~8环烷基”,可列举1-甲基环丙基、1-氰基环丙基、1-氨基羰基环丙基、1-氨基硫羰基环丙基、1-(吡啶-2-基)环丙基。
作为X中的“C3~8环烷基”上的取代基,可优选列举:氰基;氨基羰基;氨基硫羰基;甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、正己基等C1~6烷基;吡啶基、吡嗪基、嘧啶基、哒嗪基、三嗪基等6元杂芳基。
X优选为取代或未取代的环丙基,更优选为未取代的环丙基。
〔R1〕
式(I)中,R1为取代或未取代的C1~6烷基硫基、或者取代或未取代的C1~6烷基磺酰基。
作为R1中的“C1~6烷基硫基”,可列举甲基硫基、乙基硫基、正丙基硫基、异丙基硫基、正丁基硫基、异丁基硫基、仲丁基硫基、叔丁基硫基等。
作为R1中的“C1~6烷基磺酰基”,可列举甲基磺酰基、乙基磺酰基、叔丁基磺酰基等。
作为R1中的“C1~6烷基硫基”及“C1~6烷基磺酰基”上的取代基,可优选列举氟基、氯基、溴基、碘基等卤代基。
R1优选为C1~6烷基磺酰基,更优选为乙基磺酰基。
〔R2〕
式(I)中,R2为取代或未取代的C1~6烷基。
R2中的“C1~6烷基”可以为直链也可以为支链。作为“C1~6烷基”,可列举甲基、乙基、正丙基、正丁基、正戊基、正己基、异丙基、异丁基、仲丁基、叔丁基、异戊基、新戊基、2-甲基丁基、异己基等。
作为R2中的“C1~6烷基”上的取代基,可优选列举氟基、氯基、溴基、碘基等卤代基。
R2优选为未取代的C1~6烷基,更优选为甲基。
〔R〕
式(I)中,R为取代或未取代的C2~6烯基。
作为R中的“C2~6烯基”,可列举乙烯基、1-丙烯基、2-丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基等。
作为R中的“取代C2~6烯基”,可列举:2-氟-2-溴乙烯基、2,2-二氯乙烯基、2-氯-2-碘乙烯基、2-氯-1-丙烯基、2,3,3,3-四氟-1-丙烯基、3,3,3-三氟-1-丙烯基、2-氯-3,3,3-三氟-1-丙烯基、2-溴-3,3,3-三氟-1-丙烯基、3,3,3-三氟-2-三氟甲基-1-丙烯基、2-氟-1-丁烯基、3,3,4,4,4-五氟-1-丁烯基、2,3,3,4,4,4-六氟-1-丁烯基、2-氯-3,3,4,4,4-五氟-1-丁烯基、3,3,4,4,5,5,5-七氟-1-戊烯基、2-氯-3,3,4,4,5,5,5-七氟-1-戊烯基、2,3,3,4,4,5,5,5-八氟-1-戊烯基、3,3,4,4,5,5,6,6,6-九氟-1-己烯基等C2~6卤代烯基;1,2-二氟-2-三氟甲氧基乙烯基、1,2-二氟-2-全氟丙氧基乙烯基等C1~6卤代烷氧基C2~6卤代烯基。
作为R中的“取代C2~6烯基”上的取代基,可优选列举:氟基、氯基、溴基、碘基等卤代基;三氟甲氧基、2-氯-正丙氧基、2,3-二氯丁氧基、全氟丙氧基等C1~6卤代烷氧基。
R优选为C2~6卤代烯基。
化合物(I)的盐只要是农业园艺学上所允许的盐,则并无特别限制。作为化合物(I)的盐,可列举例如:盐酸、硫酸等无机酸的盐;乙酸、乳酸等有机酸的盐;锂、钠、钾等碱金属的盐;钙、镁等碱土金属的盐;铁、铜等过渡金属的盐;氨、三乙基胺、三丁基胺、吡啶、肼等有机碱的盐;等等。
〔式(II)所示的化合物〕
式(I)所示的化合物优选为式(II)所示的化合物。
[化学式16]
式(II)中,
式(II)中,
R1、R2及X表示与式(I)中的R1、R2及X同样的含义。
R3为氢原子或卤代基。
R4为C1~4卤代烷基。
式(II)中的碳-碳立体双键表示E体或Z体或者它们的混合物。
〔R3〕
作为R3中的“卤代基”,可列举氟基、氯基、溴基、碘基等。
〔R4〕
作为R4中的“C1~4卤代烷基”,可列举氟甲基、二氟甲基、三氟甲基、2,2,2-三氟乙基、五氟乙基、3,3,3-三氟丙基、2,2,3,3,3-五氟丙基、全氟丙基、2,2,2-三氟-1-三氟甲基乙基、全氟异丙基、4-氟丁基、2,2,3,3,4,4,4-七氟丁基、全氟丁基、氯甲基、溴甲基、二氯甲基、二溴甲基、三氯甲基、三溴甲基、1-氯乙基、2,2,2-三氯乙基、4-氯丁基等。
作为R4,优选氟甲基、二氟甲基、三氟甲基、2,2,2-三氟乙基、五氟乙基、3,3,3-三氟丙基、2,2,3,3,3-五氟丙基、全氟丙基、2,2,2-三氟-1-三氟甲基乙基、全氟异丙基、4-氟丁基、2,2,3,3,4,4,4-七氟丁基、全氟丁基等C1~4氟代烷基。
式(I)所示的化合物优选为以下的化合物。
[化学式17]
[化学式18]
(式(IV)中的碳-碳立体双键表示E体或Z体或者它们的混合物。)
[化学式19]
[化学式20]
[化学式21]
(式(VII)中的碳-碳立体双键表示E体或Z体或者它们的混合物。)
[化学式22]
[化学式23]
[化学式24]
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〔制造方法〕
本发明的(杂)芳基咪唑化合物并不受其制造方法的特别限定。例如,本发明的(杂)芳基咪唑化合物可以通过实施例等中记载的已知的制造方法来得到。另外,化合物(I)的N-氧化物化合物、盐等可以由化合物(I)通过已知的方法来得到。
本发明的(杂)芳基咪唑化合物例如可以通过以下所示的方法来制造。
(合成方法1)
[化学式25]
(式中,X、R1及R2为与前述的X、R1及R2相同的含义,Rf为氟甲基、二氟甲基、三氟甲基、2,2,2-三氟乙基、五氟乙基、3,3,3-三氟丙基、2,2,3,3,3-五氟丙基、全氟丙基、2,2,2-三氟-1-三氟甲基乙基、全氟异丙基、4-氟丁基、2,2,3,3,4,4,4-七氟丁基、全氟丁基等C1~4氟代烷基。)
(合成方法2)
[化学式26]
(式中,X、R1 R2及Rf为与前述的X、R1 R2及Rf相同的含义,R5为C1~6烷基。)
(合成方法3)
[化学式27]
(式中,X、R1 R2及Rf为与前述的X、R1 R2及Rf相同的含义。)
(合成方法4)
[化学式28]
(式中,X、R1 R2及Rf为与前述的X、R1 R2及Rf相同的含义。)
(合成方法5)
[化学式29]
(式中,X、R1 R2及Rf为与前述的X、R1 R2及Rf相同的含义。)
(合成方法6)
[化学式30]
(式中,X、R1 R2及Rf为与前述的X、R1 R2及Rf相同的含义。)
(合成方法7)
[化学式31]
(式中,X、R1 R2及Rf为与前述的X、R1 R2及Rf相同的含义。)
(合成方法8)
[化学式32]
(式中,X、R1 R2及Rf为与前述的X、R1 R2及Rf相同的含义。)
(合成方法9)
[化学式33]
(式中,X、R1 R2及Rf为与前述的X、R1 R2及Rf相同的含义。)
〔有害生物的防除效果〕
本发明的(杂)芳基咪唑化合物对影响植物生长的各种农业害虫及螨类等有害生物的防除效果优异。
另外,本发明的(杂)芳基咪唑化合物对作物的药害少,对鱼类、恒温动物的毒性低,因此为安全性高的物质。因此,作为杀虫剂或杀螨剂的有效成分是有用的。
此外,近年来,在小菜蛾、稻飞虱、叶蝉、蚜虫等许多害虫中发展出对各种现有药剂的抗性,产生这些药剂的效力不足的问题,期待对抗性品系的害虫也有效的药剂。本发明的(杂)芳基咪唑化合物不仅对敏感品系表现出优异的防除效果,而且对各种抗性品系的害虫以及杀螨剂抗性品系的螨类也表现出优异的防除效果。
本发明的(杂)芳基咪唑化合物对于危害人畜的体外寄生虫及体内寄生虫的防除效果优异。另外,对鱼类、恒温动物的毒性低,因此是安全性高的物质。因此,作为体外寄生虫及体内寄生虫的防除剂的有效成分是有用的。
另外,本发明的(杂)芳基咪唑化合物在作为防除对象的生物的整个生长阶段显示出效力,例如,对螨、昆虫等的卵、幼虫、幼虫、蛹、成虫显示出优异的防除效果。
〔有害生物防除剂〕
本发明的有害生物防除剂含有选自本发明的(杂)芳基咪唑化合物中的至少1者作为有效成分。本发明的有害生物防除剂中含有的(杂)芳基咪唑化合物的量只要表现出有害生物的防除效果就没有特别限制。有害生物防除剂为防除有害生物的制剂,包含杀虫或杀螨剂、体外寄生虫防除剂、或者体内寄生虫防除或驱除剂等。
本发明的有害生物防除剂也可以与杀菌剂、杀虫·杀螨剂、杀线虫剂、杀土壤害虫剂等其它有效成分;植物调节剂、增效剂、肥料、土壤改良剂、动物用饲料等混用或并用。
本发明的(杂)芳基咪唑化合物与其它有效成分的组合关于杀虫·杀螨·杀线虫活性可以期待协同效果。协同效果可以按照常规方法由Colby公式(Colby.S.R.;Calculating Synergisticand Antagonistic Responses of Herbicide Combin ations;Weeds 15,20-22页,1967)来确认。
以下示出可以与本发明的有害生物防除剂混用或并用的杀虫·杀螨剂、杀线虫剂、杀土壤害虫剂、驱虫剂等的具体例。
(1)乙酰胆碱酯酶抑制剂:
(a)氨基甲酸酯系:棉铃威(alanycarb)、涕灭威(aldicarb)、虫威(bendiocarb)、丙硫克百威(benfuracarb)、丁叉威(butocarboxim)、氧丁叉威(butoxycarboxim)、甲萘威(carbaryl)、克百威(carbofuran)、丁硫克百威(carbosulfan)、乙硫苯威(ethiofencarb)、仲丁威(fenobucarb)、伐虫脒(formetanate)、呋线威(furathiocarb)、异丙威(isoprocarb)、甲硫威(methiocarb)、灭多威(methomyl)、杀线威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、久效威(thiofanox)、唑蚜威(triazamate)、混杀威(trimetacarb)、XMC、灭杀威(xylylcarb);苯硫威(fenothiocarb)、MIPC、MPMC、MTMC、砜灭威(aldoxycarb)、除害威(allyxycarb)、灭害威(aminocarb)、合杀威(bufencarb)、除线威(cloethocarb)、威百亩钠(metam-sodium)、猛杀威(promecarb);
(b)有机磷系:乙酰甲胺磷(acephate)、甲基吡噁磷(azamethiphos)、乙基谷硫磷(azinphos-ethyl)、甲基谷硫磷(azinphos-methyl)、硫线磷(cadusafos)、氯氧磷(chlorethoxyphos)、毒虫畏(chlorfenvinphos)、氯甲磷(chlormephos)、氯吡硫磷(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、蝇毒磷(coumaphos)、杀螟腈(cyanophos)、甲基内吸磷(demeton-S-methyl)、二嗪磷(diazinon)、敌敌畏/DDVP(dichlorvos/DDVP)、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、乙拌磷(disulfoton)、EPN、乙硫磷(ethion)、丙线磷(ethoprophos)、氨磺磷(famphur)、苯线磷(fenamiphos)、杀螟硫磷(fenitrothion)、倍硫磷(fenthion)、噻唑硫磷(fosthiazate)、庚烯磷(heptenophos)、新烟磷(imicyafos)、异柳磷(isofenphos)、水胺硫磷(isocarbophos)、异唑磷(isoxathio)、马拉硫磷(malathion)、灭蚜磷(mecarbam)、甲胺磷(methamidophos)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧化乐果(omethoate)、砜吸磷(oxydemeton-methyl)、对硫磷(parathion)、甲基对硫磷(parathion-methyl)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀硫磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、辛硫磷(phoxim)、甲基嘧啶磷(pirimiphos-methyl)、丙溴磷(profenofos)、胺丙畏(propetamphos)、丙硫磷(prothiofos)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、喹硫磷(quinalphos)、治螟磷(sulfotep)、丁基嘧啶磷(tebupirimfos)、双硫磷(temephos)、特丁硫磷(terbufos)、杀虫威(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敌百虫(trichlorfon)、蚜灭多(vamidothion);乙基溴硫磷(bromophos ethyl)、BRP、三硫磷(carbophenothion)、苯腈膦(cyanofenphos)、CYAP、甲基内吸磷砜(demeton-S-methyl sulfone)、氯亚胺硫磷(dialifos)、除线磷(diclofenthion)、蔬果磷(dioxabenzofos)、乙嘧硫磷(etrimfos)、丰索磷(fensulfothion)、吡氟硫磷(flupyrazofos)、地虫硫磷(fonofos)、安果(formothion)、丁苯硫磷(fosmethilan)、氯唑磷(isazofos)、碘硫磷(jodfenphos)、虫螨畏(methacrifos)、乙基嘧啶磷(pyrimiphos-ethyl)、磷虫威(phosphocarb)、丙虫磷(propaphos)、发果(prothoate)、甲丙硫磷(sulprofos)。
(2)GABA-激动性氯离子通道拮抗剂:乙酰虫腈(acetoprole)、氯丹(chlordane)、硫丹(endosulfan)、乙虫腈(ethiprole)、氟虫腈(fipronil)、吡嗪氟虫腈(pyrafluprole)、吡啶氟虫腈(pyriprole);毒杀芬(camphechlor)、七氯(heptachlor)、除螨灵(dienochlor)。
(3)钠通道调节剂:氟丙菊酯(acrinathrin)、d-顺式-反式丙烯菊酯(d-cis-transallethrin)、d-反式丙烯菊酯(d-transarethrin)、联苯菊酯(bifenthrin)、生物丙烯菊酯(bioallethrin)、生物丙烯菊酯S-环戊基异构体(bioaresulin S-cyclopentylisomer)、生物苄呋菊酯(bioresmethrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、β-氟氯氰菊酯(β-cyfluthrin)、氯氟氰菊酯(cyhalothrin)、λ-氯氟氰菊酯(λ-cyhalothrin)、γ-氯氟氰菊酯(γ-cyhalothrin)、氯氰菊酯(cypermethrin)、α-氯氰菊酯(α-cypermethrin)、β-氯氰菊酯(β-cypermethrin)、θ-氯氰菊酯(θ-cypermethrin)、ζ-氯氰菊酯(ζ-cypermethrin)、苯氰菊酯[(1R)-反式异构体](cyphenothrin[(1R)-transisomer])、溴氰菊酯(deltamethrin)、烯炔菊酯[(EZ)-(1R)-异构体](empenthrin[(EZ)-(1R)-Isomer])、顺式氰戊菊酯(esfenvalerate)、醚菊酯(ethofenprox)、甲氰菊酯(fenpropathrine)、氰戊菊酯(fenvalerate)、氟氰戊菊酯(flucythrinate)、氟氯苯菊酯(flumethrin)、τ-氟胺氰菊酯(τ-fulvalinate)、苄螨醚(halfenprox)、炔咪菊酯(imiprothrin)、噻嗯菊酯(kadethrin)、氯菊酯(permethrin)、苯醚菊酯[(1R)-反式异构体](phenothrin[(1R)-trans isomer]、炔丙菊酯(prallethrin)、除虫菊(pyrethrum)、苄呋菊酯(resmethrin)、氟硅菊酯(silafluofen)、七氟菊酯(tefluthrin)、胺菊酯[(1R)-异构体](tetramethrin[(1R)-isomer])、四溴菊酯(tralomethrin)、四氟苯菊酯(transfluthrin);丙烯菊酯(allethrin)、除虫菊酯(pyrethrin)、除虫菊酯I(pyrethrinI)、除虫菊酯II(pyrethrin II)、丙氟菊酯(profluthrin)、四氟甲醚菊酯(dimefluthrin)、生物苄呋烯菊酯(bioethanomethrin)、生物氯菊酯(biopermethrin)、反式氯菊酯(transpermethrin)、芬氟司林(fenfluthrin)、氯氰吡菊酯(fenpirithrin)、溴氟菊酯(flubrocythrinate)、三氟醚菊酯(flufenprox)、甲氧苄氟菊酯(metofluthrin)、丙苯烃菊酯(protrifenbute)、反灭虫菊(pyresmethrin)、环戊烯丙菊酯(terallethrin)。
(4)烟碱型乙酰胆碱受体激动剂:啶虫脒(acetamiprid)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、烯啶虫胺(nitenpyram)、硝虫噻嗪(nithiazine)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)、氟啶虫胺腈(sulfoxaflor)、尼古丁(nicotine)、氟吡呋喃酮(flupyradifurone)、flupyrimin。
(5)烟碱型乙酰胆碱受体变构调节剂:乙基多杀菌素(spinetoram)、多杀菌素(spinosad)。
(6)氯离子通道活化剂:阿维菌素(abamectin)、甲氨基阿维菌素苯甲酸盐(emamectin-benzoate)、雷皮菌素(lepimectin)、密灭汀(milbemectin);伊维菌素(ivermectin)、塞拉菌素(selamectin)、多拉菌素(doramectin)、依普菌素(eprinomectin)、莫西菌素(moxidectin)、米尔倍霉素(milbemycin)、米尔贝霉素肟(milbemycin oxime)、奈马菌素(nemadectin)。
(7)保幼激素类似物:烯虫乙酯(hydroprene)、烯虫炔酯(kinoprene)、甲氧普烯(methoprene)、苯氧威(fenoxycarb)、吡丙醚(pyriproxyfen);苯虫醚(diofenolan)、保幼醚(epofenonane)、烯虫硫酯(triprene)。
(8)其它非特异性抑制剂:甲基溴(methyl bromide)、氯化苦(chloropicrin),硫酰氟(sulfuryl fluoride)、硼砂(borax)、吐酒石(tartar emetic)。
(9)同翅目选择性摄食抑制剂:氟啶虫酰胺(flonicamid)、吡蚜酮(pymetrozine)、新喹唑啉(pyrifluquinazon)。
(10)螨类生长抑制剂:四螨嗪(clofentezine)、氟螨嗪(diflovidazin)、噻螨酮(hexythiazox)、乙螨唑(etoxazole)。
(11)源自微生物的昆虫中肠内膜破坏剂:苏云金芽孢杆菌以色列亚种(bacillusthuringiensis subsp.Israelensis)、球形芽孢杆菌(bacillus sphaericus)、苏云金芽孢杆菌鲇泽亚种(bacillus thuringiensis subsp.aizawai)、苏云金芽孢杆菌库尔斯塔克亚种(bacillus thuringiensis subsp.kurstaki)、苏云金芽孢杆菌拟步行甲亚种(bacillusthuringiensis subsp.tenebrionis)、Bt作物蛋白质:Cry1Ab、Cry1Ac、Cry1Fa、Cry1A.105、Cry2Ab、Vip3A、mCry3A、Cry3Ab、Cry3Bb、Cry34Ab1/Cry35Ab1。
(12)线粒体ATP生物合成酶抑制剂:丁醚脲(diafenthiuron)、三唑锡(azocyclotin)、三环锡(cyhexatin)、苯丁锡(fenbutatin oxide)、克螨特(propargite)、三氯杀螨砜(tetradifon)。
(13)氧化磷酸化解偶联剂:溴虫腈(chlorfenapyr)、氟虫胺(sulfluramid)、DNOC;乐杀螨(binapacryl)、消螨通(dinobuton)、消螨普(dinocap)。
(14)烟碱型乙酰胆碱受体通道阻断剂:杀虫磺(bensultap)、杀螟丹盐酸盐(cartap hydrochloride);沙蚕毒素(nereistoxin);杀虫单(thiosultap-sodium)、杀虫环(thiocyclam)。
(15)壳多糖合成抑制剂:双三氟虫脲(bistrifluron)、氟啶脲(chlorfluazuron)、除虫脲(diflubenzuron)、氟环脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、虱螨脲(lufenuron)、双苯氟脲(novaluron)、多氟脲(noviflumuron)、伏虫隆(teflubenzuron)、杀铃脲(triflumuron)、噻螨酮(buprofezin)、吡虫隆(fluazuron)。
(16)双翅目蜕皮干扰剂:灭蝇胺(cyromazine)。
(17)蜕皮激素受体激动剂:环虫酰肼(chromafenozide)、氯虫酰肼(halofenozide)、甲氧虫酰肼(methoxyfenozide)、虫酰肼(tebufenozide)。
(18)章鱼胺受体激动剂:双甲脒(amitraz)、得米地曲(demiditraz)、杀虫脒(chlordimeform)。
(19)线粒体电子传递系统复合体III抑制剂:灭螨醌(acequinocyl)、嘧螨酯(fluacrylpyrim)、伏蚁腙(hydramethylnon)。
(20)线粒体电子传递系统复合体I抑制剂:喹螨醚(fenazaquin)、唑螨酯(fenpyroximate)、嘧螨醚(pyrimidifen)、哒螨灵(pyridaben)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad)、鱼藤酮(rotenone)。
(21)电压依赖性钠通道阻滞剂:茚虫威(indoxacarb)、氰氟虫腙(metaflumizone)。
(22)乙酰基CoA羧化酶抑制剂:螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)、螺虫乙酯(spirotetramat)。
(23)线粒体电子传递系统复合体IV抑制剂:磷化铝(aluminium phosphide)、磷化钙(calcium phosphide)、膦(phosphine)、磷化锌(zinc phosphide)、氰化物(cyanide)。
(24)线粒体电子传递系统复合体II抑制剂:腈吡螨酯(cyenopyrafen)、丁氟螨酯(cyflumetofen)、皮福鲁不米多(pyflubumide)。
(25)兰尼碱受体调节剂:氯虫酰胺(chlorantraniliprole)、溴氰虫酰胺(cyantraniliprole)、氟虫酰胺(fulbendiamide)、环溴虫酰胺(cyclaniliprole)、氟氰虫酰胺(tetraniliprole)。
(26)混合功能氧化酶抑制剂化合物:增效醚(piperonyl butoxide)。
(27)蛛毒素受体激动剂:缩酚酸肽(depsipeptide)、环状缩酚酸肽(cyclodepsipeptide)、24元环状缩酚酸肽(24membered cyclodepsipeptide)、艾莫德赛(emodepside)。
(28)其它药剂(作用机理未知):印楝素(azadirachtin)、苯螨特(benzoximate)、联苯肼酯(bifenazate)、溴螨酯(bromopropylate)、灭螨锰(quinomethionate)、冰晶石(cryolite)、三氯杀螨醇(dicofol)、啶虫丙醚(pyridalyl)、异噻虫唑(bencrothiaz)、硫(sulfur)、磺胺螨酯(amidoflu met)、1,3-二氯丙烯(1,3-dichloropropene)、DCIP、溴螨酯(phenisobrom olate)、苯螨特(benzomate)、四聚乙醛(metaldehyde)、乙酯杀螨醇(chlorbenzilate)、氯噻苯(clothiazoben)、环虫腈(dicyclanil)、氧嘧酰胺(fenoxacrim)、芳氟胺(fentrifanil)、氟螨噻(fulbenzimine)、氟奋乃静(fluphenazine)、诱虫十六酯(gossyplure)、日本金龟子性引诱剂(Japonilur e)、虫酮(methoxadiazone)、石油(oil)、油酸钾(potassium oleate)、杀螨好(tetrasul)、苯螨噻(trialathene);双丙环虫酯(afidopyropen)、氟麦托醌(flometoquin)、丁虫腈(flufiprole)、氟噻虫砜(fluenesulfone)、氯氟醚菊酯(meperfluthrin)、四氟醚菊酯(tetramethylfluthrin)、溴代吡咯腈(tralopyril)、四氟甲醚菊酯(dimefluthrin)、甲基新癸酰胺(methylneodecanamide);氟雷拉纳(fluralaner)、阿福拉纳(afoxolaner)、氟噁唑酰胺(fluxametamide)、5-[5-(3,5-二氯苯基)-5-三氟甲基-4,5-二氢异噁唑-3-基]-2-(1H-1,2,4-三唑-1-基)苯甲腈(CAS:943137-49-3)(5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-(1H-1,2,4-triazole-1-yl)benzonitrile(CAS:943137-49-3))、溴虫氟苯双酰胺(broflanilide)、以及间二酰胺类。
(29)驱虫剂:
(a)苯并咪唑系:芬苯达唑(fenbendazole)、阿苯达唑(albendazole)、三氯苯达唑(triclabendazole)、奥苯达唑(oxibendazole)、甲苯达唑(mebendazole)、奥芬达唑(oxfendazole)、帕苯达唑(perbendazole)、氟苯达唑(flubendazole);非班太尔(febantel)、奈韦拉平(netobimin)、托布津(thiophanate);噻苯咪唑(thiabendazole)、堪苯达唑(cambendazole);
(b)水杨酰苯胺类:氯氰碘柳胺(closantel)、五氯柳胺(oxyclozanide)、碘醚柳胺(rafoxanide)、氯硝柳胺(niclosamide);
(c)取代酚类:硝碘酚腈(nitroxinil)、硝硫氰酯(nitroscanate);
(d)嘧啶类:噻嘧啶(pyrantel)、甲噻吩嘧啶(morantel);
(e)咪唑并噻唑类:左旋咪唑(levamisole)、四咪唑(tetramisole);
(f)四氢嘧啶类:吡喹酮(praziquantel)、依西太尔(epsiprantel);
(g)其它驱虫药:环二烯(cyclodiene)、鱼尼丁(ryania)、氯舒隆(clorsulon)、甲硝唑(metronidazole)、得米地曲(demiditraz);哌嗪(piperazine)、乙胺嗪(diethylcarbamazine)、二氯芬(dichlorophen)、糠酸莫米松(monepantel)、三苯双脒(tribenzymidine)、阿米太尔(amidantel);硫乙胂胺(thiacetalsamide)、美拉索明(melarsomine)、硫乙胂胺(arsenamide)。
以下示出可以与本发明的有害生物防除剂混用或并用的杀菌剂的具体例。
(1)核酸生物合成抑制剂:
(a)RNA聚合酶I抑制剂:苯霜灵(benalaxyl)、精苯霜灵(benalaxyl-M)、呋霜灵(furalaxyl)、甲霜灵(metalaxyl)、精甲霜灵(metalaxyl-M);噁霜灵(oxadixyl);抑霉胺(clozylacon)、呋酰胺(ofurace);
(b)腺苷脱氨酶抑制剂:乙嘧酚磺酸酯(bupirimate)、甲菌定(dimethirimol)、乙嘧酚(ethirimol);
(c)DNA/RNA合成抑制剂:噁霉灵(hymexazol)、辛噻酮(octhilinone);
(d)DNA拓扑异构酶II抑制剂:噁喹酸(oxolinic acid)。
(2)有丝核分裂抑制剂及细胞分裂抑制剂:
(a)β-微管蛋白聚合抑制剂:苯菌灵(benomyl)、多菌灵(carbendazim)、苯咪唑菌(chlorfenazole)、麦穗宁(fuberidazole)、噻苯咪唑(thiabendazole);托布津(thiophanate)、甲基硫菌灵(thiophanate-methyl);乙霉威(diethofencarb);苯酰菌胺(zoxamide);噻唑菌胺(ethaboxam);
(b)细胞分裂抑制剂:戊菌隆(pencycuron);
(c)类血影蛋白(spectrin-like protein)的离域抑制剂:氟吡菌胺(fluopicolide)。
(3)呼吸抑制剂:
(a)复合体I NADH氧化还原酶抑制剂:氟嘧菌胺(diflumetorim);唑虫酰胺(tolfenpyrad);
(b)复合体II琥珀酸脱氢酶抑制剂:麦锈灵(benodanil)、氟酰胺(flutolanil)、灭锈胺(mepronil);异丙噻菌胺(isofetamide);氟吡菌酰胺(fluopyram);甲呋酰胺(fenfuram)、拌种胺(frumecyclox);萎锈灵(carboxin)、氧化萎锈灵(oxycarboxin);噻呋酰胺(tifluzamide);苯并烯氟菌唑(benzovindiflupyr)、联苯吡菌胺(bixafen)、氟唑菌酰胺(fluxapyroxad)、呋吡菌胺(furametpyr)、吡唑萘菌胺(isopyrazam)、戊苯吡菌胺(penflufen)、吡噻菌胺(penthiopyrad)、环苯吡菌胺(sedaxane);啶酰菌胺(boscalid);
(c)复合体III泛醌氧化酶Qo抑制剂:嘧菌脂(azoxystrobin)、丁香菌酯(cumoxystrobin)、甲香菌酯(cumethoxystrobin)、烯肟菌酯(enoxastrobin)、氟菌螨酯(flufenoxystrobin)、啶氧菌酯(picoxystrobin)、唑菌酯(pyraoxystrobin);吡唑醚菌酯(pyraclostrobin)、唑胺菌酯(pyrametostrobin)、氯啶菌酯(triclopyricarb);醚菌酯(kresoxim-methyl)、肟菌酯(trifloxystrobin);醚菌胺(dimoxystrobin)、烯肟菌胺(fenaminestrobin)、苯氧菌胺(metominostrobin)、肟醚菌胺(orysastrobin);噁唑菌酮(famoxadone);氟嘧菌酯(fluoxastrobin);咪唑菌酮(fenamidon);吡菌苯威(pyribencarb);
(d)复合体III泛醌还原酶Qi抑制剂:氰霜唑(cyazofamid);吲唑磺菌胺(amisulbrom);
(e)氧化磷酸化的解偶联剂:乐杀螨(binapacryl)、敌螨普(meptyldinocap)、消螨普(dinocap);氟啶胺(fluazinam);嘧菌腙(ferimzone);
(f)氧化磷酸化抑制剂(ATP合成酶的抑制剂):薯瘟锡(fentin acetate)、氯化三苯基锡(fentin chloride)、三苯基氢氧化锡(fentin hydroxide);
(g)ATP生成抑制剂:硅噻菌胺(silthiofam);
(h)复合体III:细胞色素bc1(泛醌还原酶)的Qx(未知)抑制剂:唑嘧菌胺(ametoctrazine)。
(4)氨基酸和蛋白质合成抑制剂
(a)蛋氨酸生物合成抑制剂:安朵普灵(andoprim)、嘧菌环胺(cyprodinil)、嘧菌胺(mepanipyrim)、嘧霉胺(pyrimethanil);
(b)蛋白质合成抑制剂:灭瘟素(blasticidin-S);春雷霉素(kasugamycin)、春雷霉素盐酸盐(kasugamycin hydrochloride);链霉素(streptomycin);土霉素(oxytetracycline)。
(5)信号传导抑制剂:
(a)信号传导抑制剂:喹氧灵(quinoxyfen)、丙氧喹啉(proquinazid);
(b)渗透压信号传导中的MAP·组氨酸激酶抑制剂:拌种咯(fenpiclonil)、咯菌腈(fludioxonil);乙菌利(chlozolinate)、异菌脲(iprodione)、腐霉利(procymidone)、乙烯菌核利(vinclozolin)。
(6)脂质和细胞膜合成抑制剂:
(a)磷脂生物合成、甲基转移酶抑制剂:克瘟散(edifenphos)、异稻瘟净(iprobenfos)、吡菌磷(pyrazophos);稻瘟灵(isoprothiolane);
(b)脂质的过氧化剂:联苯(biphenyl)、地茂散(chloroneb)、氯硝胺(dichloran)、五氯硝基苯(quintozene)、四氯硝基苯(tecnazene)、甲基立枯磷(tolclofos-methyl);土菌灵(etridiazole);
(c)作用于细胞膜的药剂:碘代丙炔基正丁氨基甲酸酯(iodocarb)、霜霉威(propamocarb)、霜霉威盐酸盐(propamocarb-hydrochloride)、霜霉威乙膦酸盐(propamocarb-focetylate)、硫菌威(prothiocarb);
(d)扰乱病原菌细胞膜的微生物:枯草芽孢杆菌(bacillus subtilis)、枯草芽孢杆菌QST713菌株(bacillus subtilis strain QST713)、枯草芽孢杆菌FZB24菌株(bacillus subtilis strain FZB24)、枯草芽孢杆菌MBI600菌株(bacillussubtilisstrain MBI600)、枯草芽孢杆菌D747菌株(bacillus subtilis strain D747);
(e)扰乱细胞膜的药剂:互生叶白千层(茶树)的提取物(melaleuca alternifolia(tea tree)extract)。
(7)细胞膜的甾醇生物合成抑制剂:
(a)甾醇生物合成中的C14位的脱甲基化抑制剂:嗪氨灵(triforine);啶斑肟(pyrifenox)、啶菌噁唑(pyrisoxazole);氯苯嘧啶醇(fenarimol)、呋嘧醇(flurprimidol)、氟苯嘧啶醇(nuarimol);抑霉唑(imazalil)、抑霉唑硫酸盐(imazalilsulfate)、噁咪唑(oxpoconazole)、稻瘟酯(pefurzoate)、咪鲜胺(prochloraz)、氟菌唑(triflumizole)、烯效唑(viniconazole);戊环唑(azaconazole)、双苯三唑醇(bitertanol)、糠菌唑(bromuconazole)、环唑醇(cyproconazole)、苄氯三唑醇(diclobutrazole)、苯醚甲环唑(difenoconazole)、烯唑醇(diniconazole)、烯唑醇-M(diniconazole-M)、氟环唑(epoxiconazole)、乙环唑(etaconazole)、腈苯唑(fenbuconazole)、氟喹唑(fluquinconazole)、氟硅唑(flusilazole)、粉唑醇(flutriafol)、氟康唑(fluconazole)、顺式氟康唑(fluconazole-cis)、己唑醇(hexaconazole)、亚胺唑(imibenconazole)、种菌唑(ipconazole)、叶菌唑(metconazole)、腈菌唑(myclobutanil)、戊菌唑(penconazole)、丙环唑(propiconazole)、喹康唑(fluquinconazole)、硅氟唑(simeconazole)、戊唑醇(tebuconazole)、氟醚唑(tetraconazole)、三唑酮(triadimefon)、三唑醇(triadimenol)、灭菌唑(triticonazole);丙硫菌唑(prothioconazole)、伏立康唑(voriconazole);
(b)甾醇生物合成中的Δ14还原酶及Δ8→Δ7-异构酶的抑制剂:十二吗啉(aldimorph)、十二环吗啉(dodemorph)、十二环吗啉乙酸盐(dodemorph acetate)、丁苯吗啉(fenpropimorph)、十三吗啉(tridemorph);苯锈啶(fenpropidin)、粉病灵(piperalin);螺环菌胺(spiroxamine);
(c)甾醇生物合成体系的C4位脱甲基化中的3-酮还原酶抑制剂:环酰菌胺(fenhexamid);胺苯吡菌酮(fenpyrazamine);
(d)甾醇生物合成体系的角鲨烯环氧酶抑制剂:稗草丹(pyribaticarb);萘替芬(naftifen)、特比萘芬(terbinafine)。
(8)细胞壁合成抑制
(a)海藻糖酶抑制剂:井冈霉素(validamycin);
(b)壳多糖合成酶抑制剂:多抗霉素(polyoxin)、多氧霉素(polyoxorim);
(c)纤维素合成酶抑制剂:烯酰吗啉(dimethomorph)、氟吗啉(flumorph)、丁吡吗啉(pyrimorph);苯噻菌胺(benthiavalicarb-isopropyl)、丙森锌(iprovalicarb)、tolprocarb、霜霉灭(valifenalate);双炔酰菌胺(mandipropamid)。
(9)黑色素生物合成抑制剂
(a)黑色素生物合成的还原酶抑制剂:四氯苯酞(fthalide);咯喹酮(pyroquilon);三环唑(tricyclazole);
(b)黑色素生物合成的脱水酶抑制剂:环丙酰菌胺(carpropamid);双氯氰菌胺(diclocymet);氰菌胺(fenoxanil)。
(10)宿主植物的抗性诱导剂:
(a)作用于水杨酸合成途径的药剂:阿拉酸式苯-S-甲基(acibenzolar-S-methyl);
(b)其它:烯丙苯噻唑(probenazole);噻酰菌胺(tiadinil);异噻菌胺(isotianil);昆布多糖(laminarin);大虎杖提取液(reynoutria sachalinensisextract)。
(11)作用机制不明的药剂:霜脲氰(cymoxanil)、三乙膦酸铝(fosetyl-aluminum)、磷酸(磷酸盐)(phosphoric acid(phosphate))、叶枯酞(tecloftalam)、咪唑嗪(triazoxide)、磺菌胺(flusulfamide)、哒菌清(diclomezine)、磺菌威(methasulfocarb)、环氟菌胺(cyflufenamid)、苯菌酮(metrafenone)、甲氧苯唳菌(pyriofenone)、多果定(dodine)、多果定游离碱(dodine free base)、氟噻菌净(flutianil)。
(12)具有多作用点的药剂:铜(铜盐)(copper(copper salt))、波尔多液(bordeaux mixture)、氢氧化铜(copper hydroxide)、萘二甲酸铜(copper naphthalate)、氧化铜(copper oxide)、氧氯化铜(copper oxychloride)、硫酸铜(copper sulfate)、硫(sulfur)、硫制品(sulfur product)、多硫化钙(calcium polysulfide);福美铁(ferbam)、代森锰锌(mancozeb)、代森锰(maneb)、代森锰铜(mancopper)、代森联(metiram)、代森福美锌(polycarbamate)、丙森锌(propineb)、福美双(thiram)、代森锌(zineb)、福美锌(ziram);克菌丹(captan)、敌菌丹(captahol)、灭菌丹(folpet);百菌清(chlorotalonil);抑菌灵(dichlofluanid)、对甲抑菌灵(tolylfluanid);双胍辛胺(guazatine)、双胍辛胺乙酸盐(iminoctadine triacetate)、双胍三辛烷基苯磺酸盐(iminoctadinetrialbesilate);敌菌灵(anilazine);二噻农(dithianon);灭螨猛(chinomethionate);唑呋草(fluorimide)。
(13)其它药剂:DBEDC、氟灭菌丹(fluorofolpet)、双胍辛乙酸盐(guazatineacetate)、双(8-羟基喹啉)铜(II)(bis(8-quinolinolato)copper(II))、丙烷脒(propamidine)、氯化苦(chloropicrin)、酯菌胺(cyprofuram)、农杆菌(agrobacterium)、贝斯氧杂嗪(bethoxazin)、二苯胺(diphenylamine),异硫氰酸甲酯(MITC)(methylisothiocyanate)、米多霉素(mildiomycin)、辣椒素(capsaicin)、硫杂灵(cufraneb)、环丙磺酰胺(cyprosulfamide)、棉隆(dazomet)、咪菌威(debacarb)、双氯酚(dichlorophen)、野燕枯(difenzoquat)、野燕枯甲基硫酸盐(difenzoquat methylsulfate)、氟联苯菌(flumetover)、乙膦钙(fosetyl-calcium)、乙膦钠(fosetyl-sodium)、人间霉素(irumamycin)、纳他霉素(natamycin)、酞菌酯(nitrothal isopropyl)、奥克斯莫卡宾(oxamocarb)、丙诺新钠盐(propanosine sodium)、硝吡咯菌素(pyrrolnitrin)、异丁乙氧喹啉(tebufloquin)、甲磺菌胺(tolnifanide)、氰菌胺(zaliramide)、阿尔古菲斯(Algophase)、拌种灵(amicarthiazol)、氟噻唑吡乙酮(oxathiapiprolin)、代森联锌(metiram zinc)、苯噻硫氰(benthiazol)、水杨菌胺(trichlamide)、优康唑(uniconazole)、灭粉霉素(mildiomycin)、氧代奋欣(oxyfenthiin)、四唑吡氨酯(picarbutrazox)。
以下示出可以与本发明的有害生物防除剂混用或并用的植物调节剂的具体例。
脱落酸(abscisic acid)、激动素(kinetin)、苄氨基嘌呤(Benzylaminopurine)、1,3-二苯基脲(1,3-diphenylurea)、氯吡脲(forchlorfenuron)、噻苯隆(thidiazuron)、氯吡苯脲(chlorfenuron)、二氢玉米素(dihydrozeatin)、赤霉素A(gibberellin A)、赤霉素A4(gibberellin A4)、赤霉素A7(gibberellin A7)、赤霉素A3(gibberellin A3)、1-甲基环丙烷(1-methylcyclopropane)、N-乙酰氨基乙氧基乙烯基甘氨酸(别名:艾维激素)(N-acetyl aminoethoxyvinyl glycine(aviglycine))、氨基氧乙酸(aminooxyacetate)、硝酸银(silver nitrate)、氯化钴(cobalt chloride)、IAA、4-CPA、调果酸(cloprop)、2,4-D、MCPB、吲哚-3-丁酸(indole-3-butyrate)、2,4-滴丙酸(dichlorprop)、酚硫杀(phenothiol)、1-萘乙酰胺(1-naphthyl acetamide)、吲熟酯(ethychlozate)、坐果酸(cloxyfonac)、马来酰肼(maleic acid hydrazide)、2,3,5-三碘苯甲酸(2,3,5-triiodobenzoic acid)、水杨酸(salicylic acid)、水杨酸甲酯(methyl salicylate)、(-)-茉莉酮酸((-)-jasmonic acid)、茉莉酮酸甲酯(methyl jasmonate)、(+)-独脚金醇((+)-strigol)、(+)-脱氧独脚金醇((+)-deoxystrigol)、(+)-列当醇((+)-orobanchol)、(+)-高粱内酯((+)-sorgolactone)、4-氧代-4-(2-苯乙基)氨基丁酸(4-oxo-4-(2-phenylethyl)aminobutyric acid)、乙烯利(ethephon)、矮壮素(chlormequat)、甲哌啶(mepiquat chloride)、苄基腺嘌呤(benzyladenine)、5-氨基乙酰丙酸(5-amino levulinic acid)。
〔杀虫或杀螨剂〕
本发明的杀虫或杀螨剂含有选自本发明的(杂)芳基咪唑化合物中的至少1者作为有效成分。本发明的杀虫或杀螨剂中含有的(杂)芳基咪唑化合物的量只要表现出杀虫或杀螨效果就没有特别限制。
本发明的杀虫或杀螨剂优选对谷物类;蔬菜类;根菜类;球茎类;花卉类;果树类;观叶植物、茶、咖啡、可可等树木类;牧草类;禾本类;棉花等植物使用。
在对植物的施用中,本发明的有害生物防除剂、或者杀虫或杀螨剂可以用于叶、茎、柄、花、蕾、果实、种子、芽、根、块茎、块根、幼苗、插条等中的任一部位。
另外,本发明的杀虫或杀螨剂不受所施用的植物的品种的特别限制。作为植物的品种,例如可举出原种、变种、改良品种、栽培品种、突变体、杂交体、转基因体(GMO)等。
为了防除各种农业害虫及螨类,本发明的杀虫或杀螨剂可以用于种子处理、茎叶散布、土壤施用、水面施用等。
以下示出可利用本发明的杀虫或杀螨剂来防除的各种农业害虫和螨类的具体例。
(1)鳞翅目(Lepidoptera)的蝶或蛾
(a)灯蛾科(Arctiidae)的蛾:例如,美国白蛾(Hyphantria cunea)、奇特望灯蛾(Lemyra imparilis);
(b)稜巢蛾科(Bucculatricidae)的蛾:例如,梨角折蛾(Bucculatrixpyrivorella);
(c)蛀果蛾科(Carposinidae):例如,桃蛀果蛾(Carposina sasakii);
(d)草螟科(Crambidae)的蛾:例如,绢野螟属(Diaphania spp.)的瓜绢野螟(Diaphania indica)、黄瓜绢野螟(Diaphania nitidalis);例如,秆野螟属(Ostriniaspp.)的亚洲玉米螟(Ostrinia furnacalis)、欧洲玉米螟(Ostrinia nubilalis)、麻田豆杆野螟(Ostrinia scapulalis);以及二化螟(Chilo suppressalis)、稻纵卷叶螟(Cnaphalocrocis medinalis)、桃蛀螟(Conogethes punctiferalis)、西南玉米螟(Diatraea grandiosella)、桑绢野螟(Glyphodes pyloalis)、菜螟(Hellula undalis)、早熟禾拟茎草螟(Parapediasia teterrella);
(e)麦蛾科(Gelechiidae)的蛾:例如,甘薯麦蛾(Helcystogrammatriannulella)、棉红铃虫(Pectinophora gossypiella)、马铃薯块茎蛾(Phthorimaeaoperculella)、麦蛾(Sitotroga cerealella);
(f)尺蛾科(Geometridae)的蛾:例如,大造桥虫(Ascotis selenaria);
(g)细蛾科(Gracillariidae)的蛾:例如,茶细蛾(Caloptilia theivora)、柑桔潜叶蛾(Phyllocnistis citrella)、金纹细蛾(Phyllonorycter ringoniella);
(h)弄蝶科(Hesperiidae)的蝶:例如,直纹稻弄蝶(Parnara guttata);
(i)枯叶蛾科(Lasiocampidae)的蛾:例如,天幕毛虫(Malacosoma neustria);
(j)毒蛾科(Lymantriidae)的蛾:例如,毒蛾属(Lymantria spp.)的舞毒蛾(Lymantria dispar)、模毒蛾(Lymantria monacha);其它的茶毛虫(Euproctispseudoconspersa)、旋古毒蛾(Orgyia thyellina);
(k)潜蛾科(Lyonetiidae)的蛾:例如,潜蛾属(Lyonetia spp.)的桃潜叶蛾(Lyonetia clerkella)、银纹潜叶蛾(Lyonetia prunifoliella malinella);
(l)夜蛾科(Noctuidae)的蛾:例如,灰翅夜蛾属(Spodoptera spp.)的淡剑袭夜蛾(Spodoptera depravata)、南部灰翅夜蛾(Spodoptera eridania)、甜菜夜蛾(Spodopteraexigua)、草地夜蛾(Spodoptera frugiperda)、非洲棉叶虫蛾(Spodoptera littoralis)、斜纹夜蛾(Spodoptera litura);例如,丫纹夜蛾属(Autographa spp.)的银纹夜蛾(Autographa gamma)、黑点丫纹夜蛾(Autographa nigrisigna);例如,地夜蛾属(Agrotisspp.)的小地老虎(Agrotis ipsilon)、芜菁夜蛾(Agrotis segetum);例如,铃夜蛾属(Helicoverpa spp.)的棉铃虫(Helicoverpa armigera)、烟夜蛾(Helicoverpa assulta)、谷实夜蛾(Helicoverpa zea);例如,实夜蛾属(Heliothis spp.)的棉铃虫(Heliothisarmigera)、烟芽夜蛾(Heliothis virescens);其它的白斑烦夜蛾(Aedia leucomelas)、银纹夜蛾(Ctenoplusia agnata)、枯叶夜蛾(Eudocima tyrannus)、甘蓝夜蛾(Mamestrabrassicae)、粘虫(Mythimna separata)、稻螟蛉(Naranga aenescens)、松切蛾(Panolisjaponica)、疆夜蛾(Peridroma saucia)、大豆夜蛾(Pseudoplusia includens)、粉纹夜蛾(Trichoplusia ni);
(m)瘤蛾科(Nolidae)的蛾:例如,棉斑实蛾(Earias insulana);
(n)粉蝶科(Pieridae)的蝶:例如,粉蝶属(Pieris spp.)的欧洲粉蝶(Pierisbrassicae)、纹白蝶(Pieris rapae crucivora);
(o)菜蛾科(Plutellidae)的蛾:例如,葱菜蛾属(Acrolepiopsis spp.)的葱菜蛾(Acrolepiopsis sapporensis)、铃木伪菜蛾(Acrolepiopsis suzukiella);以及小菜蛾(Plutella xylostella);
(p)螟蛾科(Pyralidae)的蛾:例如,粉斑螟蛾(Cadra cautella)、小玉米茎蛀虫(Elasmopalpus lignosellus)、豆荚斑螟(Etiella zinckenella)、大蜡螟(Galleriamellonella);
(q)天蛾科(Sphingidae)的蛾:例如,天蛾属(Manduca spp.)的番茄天蛾(Manducaquinquemaculata)、烟草天蛾(Manduca sexta);
(r)举肢蛾科(Stathmopodidae)的蛾:例如,柿举肢蛾(Stathmopoda masinissa);
(s)谷蛾科(Tineidae)的蛾:例如,衣蛾(Tinea translucens);
(t)卷蛾科(Tortricidae)的蛾:例如,褐带卷蛾属(Adoxophyes spp.)的茶小卷叶蛾(Adoxophyes honmai)、苹小卷叶蛾(Adoxophyes orana);例如,黄卷蛾属(Archipsspp.)的梨黄卷蛾(Archips breviplicanus)、苹果黄卷蛾(Archips fuscocupreanus);其它的云杉芽卷蛾(Choristoneura fumiferana)、苹果蠹蛾(Cydia pomonella)、女贞细卷蛾(Eupoecilia ambiguella)、梨小食心虫(Grapholitha molesta)、后黄卷叶蛾(Homonamagnanima)、大豆食心虫(Leguminivora glycinivorella)、葡萄花翅小卷蛾(Lobesiabotrana)、豆小卷叶蛾(Matsumuraeses phaseoli)、苹褐卷蛾(Pandemis heparana)、葡萄长须卷叶蛾(Sparganothis pilleriana);
(u)巢蛾科(Yponomeutidae)的蛾:例如,苹果银蛾(Argyresthia conjugella)。
(2)缨翅目(Thysanoptera)害虫
(a)管蓟马科(Phlaeothripidae)的:例如,柿管蓟马(Ponticulothripsdiospyrosi);
(b)蓟马科(Thripidae)的:例如,花蓟马属(Frankliniella spp.)的水稻花蓟马(Frankliniella intonsa)、西花蓟马(Frankliniella occidentalis);例如,蓟马属(Thrips spp.)的棕榈蓟马(Thrips palmi)、烟蓟马(Thrips tabaci);其它的温室蓟马(Heliothrips haemorrhoidalis)、茶黄蓟马(Scirtothrips dorsalis)。
(3)半翅目(Hemiptera)的害虫
(A)古喙亚目(Archaeorrhyncha)
(a)飞虱科(Delphacidae)的:例如,灰飞虱(Laodelphax striatella)、褐飞虱(Nilaparvata lugens)、甘蔗扁角飞虱(Perkinsiella saccharicida)、白背飞虱(Sogatella furcifera)。
(B)盾喙亚目(Clypeorrhyncha)
(a)叶蝉科(Cicadellidae)的:例如,小绿叶蝉属(Empoasca spp.)的马铃薯小绿叶蝉(Empoasca fabae)、日本小绿叶蝉(Empoasca nipponica)、小贯小绿叶蝉(Empoascaonukii)、板井小绿叶蝉(Empoasca sakaii);其它的葡萄斑叶蝉(Arboridia apicalis)、黑胸二室叶蝉(Balclutha saltuella)、二点大叶蝉(Epiacanthus stramineus)、黑额二叉叶蝉(Macrosteles striifrons)、黑尾叶蝉(Nephotettix cinctinceps)。
(C)异翅亚目(Heteroptera)
(a)蛛缘蝽科(Alydidae)的:例如,点蜂缘椿象(Riptortus clavatus);
(b)缘蝽科(Coreidae)的:例如,稻棘缘蝽(Cletus punctiger)、中稻缘蝽(Leptocorisa chinensis);
(c)长蝽科(Lygaeidae)的:例如,美洲谷长蝽(Blissusleucopterus)、甘蔗异背长蝽(Cavelerius saccharivorus)、葫芦长蝽(Togo hemipterus);
(d)盲蝽科(Miridae)的:例如,日本跳盲蝽(Halticus insularis)、美国牧草盲蝽(Lygus lineolaris)、棉盲蝽(Psuedatomoscelis seriatus)、西伯利亚狭盲蝽(Stenodemasibiricum)、赤条纤盲蝽(Stenotus rubrovittatus)、赤须盲蝽(Trigonotyluscaelestialium);
(e)蝽科(Pentatomidae)的:例如,绿蝽属(Nezara spp.)的黑须稻绿蝽(Nezaraantennata)、稻绿蝽(Nezara viridula);例如,二星蝽属(Eysarcoris spp.)的北二星蝽(Eysarcoris aeneus)、日本二星蝽(Eysarcoris lewisi)、广二星蝽(Eysarcorisventralis);其它的细毛蝽(Dolycoris baccarum)、皱纹菜蝽(Eurydema rugosum)、青蝽(Glaucias subpunctatus)、茶翅蝽(Halyomorpha halys)、璧蝽(Piezodorus hybneri)、珀蝽(Plautia crossota)、稻黑蝽(Scotinophora lurida);
(f)红蝽科(Pyrrhocoridae)的:例如,离斑棉红蝽(Dysdercus cingulatus);
(g)姬缘蝽科(Rhopalidae)的:例如,黄伊缘蝽(Rhopalus msculatus);
(h)盾蝽科(Scutelleridae)的:例如,麦扁盾蝽(Eurygasterintegriceps);
(i)网蝽科(Tingidae)的:例如,梨冠网蝽(Stephanitis nashi)。
(D)腹吻亚目(Sternorrhyncha)
(a)球蚜科(Adelgidae)的:例如,落叶松球蚜(Adelges laricis);
(b)粉虱科(Aleyrodidae)的:例如,小粉虱属(Bemisia spp.)的银叶粉虱(Bemisia argentifolii)、烟粉虱(Bemisia tabaci);其它的黑刺粉虱(Aleurocanthusspiniferus)、柑橘粉虱(Dialeurodes citri)、温室白粉虱(Trialeurodesvaporariorum);
(c)蚜科(Aphididae)的:例如,蚜属(Aphis spp.)的豆蚜(Aphis craccivora)、黑豆蚜(Aphis fabae)、草莓根蚜(Aphis forbesi)、棉蚜(Aphis gossypii)、苹蚜(Aphispomi)、接骨木蚜(Aphis sambuci)、绣线菊蚜(Aphis spiraecola);例如,缢管蚜属(Rhopalosiphum spp.)的玉米蚜(Rhopalosiphum maidis)、禾谷缢管蚜(Rhopalosiphumpadi);例如,西圆尾蚜属(Dysaphis spp.)的玫瑰苹果蚜(Dysaphis plantaginea)、居根西圆尾蚜(Dysaphis radicola);例如,长管蚜属(Macrosiphum spp.)的麦长管蚜(Macrosiphum avenae)、大戟长管蚜(Macrosiphum euphorbiae);例如,瘤蚜属(Myzusspp.)的李瘤蚜(Myzus cerasi)、桃蚜(Myzus persicae)、黄药子瘤蚜(Myzus varians);其它的豌豆蚜(Acyrthosiphon pisum)、茄沟无网蚜(Aulacorthum solani)、金盏菊李短尾蚜(Brachycaudus helichrysi)、甘蓝蚜(Brevicoryne brassicae)、草莓钉蚜(Chaetosiphonfragaefolii)、桃粉大尾蚜(Hyalopterus pruni)、茶藨苦菜超瘤蚜(Hyperomyzuslactucae)、萝卜蚜(Lipaphis erysimi)、巢菜修尾蚜(Megoura viciae)、麦无网长管蚜(Metopolophium dirhodum)、莴苣衲长管蚜(Nasonovia ribis-nigri)、指头蚜(Phorodonhumuli)、麦二叉蚜(Schizaphis graminum)、麦长管蚜(Sitobion avenae)、橘二叉蚜(Toxoptera aurantii);
(d)蜡蚧科(Coccidae)的:例如,蜡蚧属(Ceroplastes spp.)的角蜡蚧(Ceroplastes ceriferus)、红蜡蚧(Ceroplastes rubens);
(e)盾蚧科(Diaspididae)的:白盾蚧属(Pseudaulacaspis spp.)的桑白蚧(Pseudaulacaspis pentagona)、李白盾蚧(Pseudaulacaspis prunicola);例如,矢尖蚧属(Unaspis spp.)的卫矛矢尖蚧(Unaspis euonymi)、柑桔矢尖蚧(Unaspis yanonensis);其它的红圆蚧(Aonidiella aurantii)、圣琼斯康盾蚧(Comstockaspis perniciosa)、茶围盾蚧(Fiorinia theae)、牡丹网盾蚧(Pseudaonidia paeoniae);
(f)硕蚧科(Margarodidae)的:例如,草履蚧(Drosicha corpulenta)、吹绵蚧(Icerya purchasi);
(g)根瘤蚜科(Phylloxeridae)的:例如,葡萄根瘤蚜(Viteus vitifolii);
(h)粉蚧科(Pseudococcidae)的:例如,臀纹粉蚧属(Planococcus spp.)的柑桔粉蚧(Planococcus citri)、日本臀纹粉蚧(Planococcus kuraunhiae);其它的石蒜绵粉蚧(Phenacoccus solani)、康氏粉蚧(Pseudococcus comstocki);
(i)木虱科(Psyllidae)的:例如,木虱属(Psylla spp.)的苹木虱(Psylla mali)、梨木虱(Psylla pyrisuga);其它的柑橘木虱(Diaphorina citri)。
(4)多食亚目(Polyphaga)的害虫
(a)番死虫科(Anobiidae)的:例如,烟草甲(Lasioderma serricorne);
(b)卷象科(Attelabidae)的:例如,梨卷叶象甲(Byctiscus betulae)、日本苹虎(Rhynchites heros);
(c)长蠢科(Bostrichidae)的:例如,褐粉蠹(Lyctus brunneus);
(d)三锥象甲科(Brentidae)的:例如,甘薯蚁象(Cylas formicarius);
(e)吉丁科(Buprestidae)的:例如,梨窄吉丁(Agrilus sinuatus);
(f)天牛科(Cerambycidae)的:例如,白斑星天牛(Anoplophora malasiaca)、松墨天牛(Monochamus alternatus)、黄星天牛(Psacothea hilaris)、葡萄脊虎天牛(Xylotrechus pyrrhoderus);
(g)叶甲科(Chrysomelidae)的:例如,豆象属(Bruchus spp.)的豌豆象(Bruchuspisorum)、蚕豆象(Bruchus rufimanus);例如,叶甲属(Diabrotica spp.)的北方玉米根虫甲(Diabrotica barberi)、十一星黄瓜甲虫(Diabrotica undecimpunctata)、玉米根萤叶甲(Diabrotica virgifera);例如,黄条跳甲属(Phyllotreta spp.)的大豆淡足跳甲(Phyllotreta nemorum)、黄曲条跳甲(Phyllotreta striolata);其它的黄守瓜(Aulacophora femoralis)、绿豆象(Callosobruchus chinensis)、甜菜大龟甲(Cassidanebulosa)、甜菜跳甲(Chaetocnema concinna)、马铃薯甲虫(Leptinotarsadecemlineata)、水稻负泥虫(Oulema oryzae)、狭胸蚤跳甲(Psylliodes angusticollis);
(h)瓢虫科(Coccinellidae)的:例如,食植瓢虫属(Epilachna spp.)的墨西哥豆瓢虫(Epilachna varivestis)、二十八星瓢虫(Epilachna vigintioctopunctata);
(i)象甲科(Curculionidae)的:例如,花象属(Anthonomus spp.)的棉铃象甲虫(Anthonomus grandis)、梨花象(Anthonomus pomorum);例如,谷象属(Sitophilus spp.)的谷象(Sitophilus granarius)、玉米象(Sitophilus zeamais);其它的稻象甲(Echinocnemus squameus)、西印度甘薯象甲(Euscepes postfasciatus)、欧洲松树皮象(Hylobius abietis)、苜蓿叶象(Hypera postica)、稻水象甲(Lissohoptrusoryzophilus)、葡萄黑象甲(Otiorhynchus sulcatus)、豌豆根瘤象(Sitona lineatus)、猎食谷象(Sphenophorus venatus);
(j)叩甲科(Elateridae)的:例如,梳爪叩甲属(Melanotus spp.)的褐纹金针虫(Melanotus fortnumi)、栉叩头虫(Melanotus tamsuyensis);
(k)露尾甲科(Nitidulidae)的:例如,姬扁出尾虫(Epuraea domina);
(l)金龟子科(Scarabaeidae)的:例如,异丽金龟属(Anomala spp.)的赤铜丽金龟(Anomala cuprea)、红铜丽金龟(Anomala rufocuprea);其它的金花金龟(Cetoniaaurata)、小青花金龟(Gametis jucunda)、豆黄鳃金龟(Heptophylla picea)、大栗鳃角金龟(Melolontha melolontha)、日本金龟子(Popillia japonica);
(m)小蠹科(Scolytidae)的:例如,云杉八齿小蠹(Ips typographus);
(n)隐翅虫科(Staphylinidae)的:例如,红胸隐翅虫(Paederus fuscipes);
(o)拟步甲科(Tenebrionidae)的:例如,黄粉虫(Tenebrio molitor)、赤拟谷盗(Tribolium castaneum);
(p)谷盗科(Trogossitidae)的:例如,大谷盗(Tenebroides mauritanicus)。
(5)双翅目(Diptera)的害虫
(A)短角亚目(Brachycera)
(a)潜蝇科(Agromyzidae)的:例如,斑潜蝇属(Liriomyza spp.)的番茄斑潜蝇(Liriomyza bryoniae)、葱潜叶蝇(Liriomyza chinensis)、美洲斑潜蝇(Liriomyzasativae)、三叶斑潜蝇(Liriomyza trifolii);其它的豌豆潜叶蝇(Chromatomyiahorticola)、日本稻潜蝇(Agromyza oryzae);
(b)花蝇科(Anthomyiidae)的:例如,地种蝇属(Delia spp.)的种蝇(Deliaplatura)、甘蓝根蝇(Delia radicum);其它的油菜肖藜泉蝇(Pegomya cunicularia);
(c)果蝇科(Drosophilidae)的:例如,果蝇属(Drosophila spp.)的黑腹果蝇(Drosophila melanogaster)、斑翅果蝇(Drosophila suzukii);
(d)水蝇科(Ephydridae)的:例如,水稻潜叶蝇(Hydrellia griseola);
(e)茎蝇科(Psilidae)的:例如,胡萝卜茎蝇(Psila rosae);
(f)实蝇科(Tephritidae)的:例如,果实蝇属(Bactrocera spp.)的瓜实蝇(Bactrocera cucurbitae)、橘小实蝇(Bactrocera dorsalis);例如,绕实蝇属(Rhagoletis spp.)的樱桃绕实蝇(Rhagoletis cerasi)、苹果绕实蝇(Rhagoletispomonella);其它的地中海果蝇(Ceratitis capitata)、橄榄果蝇(Dacus oleae)。
(B)长角亚目(Nematocera)
(a)瘿蚊科(Cecidomyiidae)的:例如,大豆荚瘿蚊(Asphondylia yushimai)、高粱瘿蚊(Contarinia sorghicola)、黑森瘿蚊(Mayetiola destructor)、麦红吸浆虫(Sitodiplosis mosellana)。
(6)直翅目(Orthoptera)的害虫
(a)蝗科(Acrididae)的:例如,沙漠蝗属(Schistocerca spp.)的南美沙漠蝗(Schistocerca americana)、沙漠蝗(Schistocerca gregaria);其它的澳大利亚灾蝗(Chortoicetes terminifera)、摩洛哥戟纹蝗(Dociostaurus maroccanus)、东亚飞蝗(Locusta migratoria)、褐飞蝗(Locustana pardalina)、红翅蝗(Nomadacrisseptemfasciata)、小翅稻蝗(Oxya yezoensis);
(b)蟋蟀科(Gryllidae)的:例如,家蟋蟀(Acheta domestica)、黄脸油葫芦(Teleogryllus emma);
(c)蝼蛄科(Gryllotalpidae)的:例如,东方蝼蛄(Gryllotalpa orientalis);
(d)螽斯科(Tettigoniidae)的:例如,温室灶马(Tachycines asynamorus)。
(7)蜱螨亚纲类(Acari)
(A)无气门目(Astigmata)的粉螨亚目类(Acaridida)
(a)粉螨科(Acaridae)的螨:例如,根螨属(Rhizoglyphus spp.)的刺足根螨(Rhizoglyphus echinopus)、罗宾根螨(Rhizoglyphus robini);例如,食酪螨属(Tyrophagus spp.)的瓜食酪螨(Tyrophagus neiswanderi)、尘食酪螨(Tyrophagusperniciosus)、腐食酪螨(Tyrophagus putrescentiae)、似食酪螨(Tyrophagus similis);其它的粗脚粉螨(Acarus siro)、椭圆食粉螨(Aleuroglyphus ovatus)、菌食嗜菌螨(Mycetoglyphus fungivorus);
(B)前气门目(Prostigmata)的辐螨亚目类(Actinedida)
(a)叶螨科(Tetranychidae)的螨:例如,苔螨属(Bryobia spp.)的苜蓿苔螨(Bryobia praetiosa)、果苔螨(Bryobia rubrioculus);例如,始叶螨属(Eotetranychusspp.)的六点始叶螨(Eotetranychus asiaticus)、北始叶螨(Eotetranychus boreus)、朴始叶螨(Eotetranychus celtis)、膝状始叶螨(Eotetranychus geniculatus)、柑橘始叶螨(Eotetranychus kankitus)、李始叶螨(Eotetranychus pruni)、栲始叶螨(Eotetranychusshii)、史氏始叶螨(Eotetranychus smithi)、桑始叶螨(Eotetranychussuginamensis)、弯钩始叶螨(Eotetranychus uncatus);例如,小爪螨属(Oligonychusspp.)的柳杉小爪螨(Oligonychus hondoensis)、冬青小爪螨(Oligonychus ilicis)、落叶松小爪螨(Oligonychus karamatus)、芒果小爪螨(Oligonychus mangiferus)、甘蔗小爪螨(Oligonychus orthius)、鳄梨小爪螨(Oligonychus perseae)、虾夷云杉叶螨(Oligonychus pustulosus)、真梶小爪螨(Oligonychus shinkajii)、针叶小爪螨(Oligonychus ununguis);例如,全爪螨属(Panonychus spp.)的桔全爪螨(Panonychuscitri)、桑全爪螨(Panonychus mori)、苹果全爪螨(Panonychus ulmi);例如,叶螨属(Tetranychus spp.)的朱砂叶螨(Tetranychus cinnabarinus)、神泽氏叶螨(Tetranychuskanzawai)、卢氏叶螨(Tetranychus ludeni)、柞木叶螨(Tetranychus quercivorus)、豆叶螨(Tetranychus phaselus)、二斑叶螨(Tetranychus urticae)、山楂叶螨(Tetranychusviennensis)、伊氏叶螨(Tetranychus evansi);例如,例如,缺爪螨属(Aponychus spp.)的竹缺爪螨(Aponychus corpuzae)、梧桐缺爪螨(Aponychus firmianae);例如,绿叶螨属(Sasanychus spp.)的绿叶螨(Sasanychus akitanus)、姬绿叶螨(Sasanychus pusillus);例如,裂爪螨属(Shizotetranychus spp.)的嗜竹裂爪螨(Shizotetranychus celarius)、长肌裂爪螨(Shizotetranychus longus)、芒草裂爪螨(Shizotetranychus miscanthi)、勒氏裂爪螨(Shizotetranychus recki)、柳裂爪螨(Shizotetranychus schizopus);以及酢浆草如叶螨(Tetranychina harti)、孔雀杜克叶螨(Tuckerella pavoniformis)、札幌叶螨(Yezonychus sapporensis);
(b)细须螨科(Tenuipalpidae)的螨:例如,短须螨属(Brevipalpus spp.)的刘氏短须螨(Brevipalpus lewisi)、卵形短须螨(Brevipalpus obovatus)、紫红短须螨(Brevipalpus phoenicis)、仙人掌短须螨(Brevipalpus russulus)、加州短须螨(brevipalpus californicus);例如,细须螨属(Tenuipalpus spp.)的太平洋细须螨(Tenuipalpus pacificus)、柿细须螨(Tenuipalpus zhizhilashviliae);以及菠萝长叶螨(Dolichotetranychus floridanus);
(c)瘿螨科(Eriophyidae)的螨:例如,瘤瘿螨属(Aceria spp.)的柿子芽螨(Aceria diospyri)、无花果瘤瘿螨(Aceria ficus)、日本瘤瘿螨(Aceria japonica)、枸杞瘤瘿螨(Aceria kuko)、石竹瘤瘿螨(Aceria paradianthi)、枸杞叶潜瘤瘿螨(Aceriatiyingi)、郁金香瘤瘿螨(Aceria tulipae)、结缕草瘤瘿螨(Aceria zoysiea);例如,瘿螨属(Eriophyes spp.)的伪梨锈蜱(Eriophyes chibaensis)、梅瘿螨(Eriophyesemarginatae);例如,刺皮瘿螨属(Aculops spp.)的番茄刺皮瘿螨(Aculopslycopersici)、皮氏刺皮瘿螨(Aculops pelekassi);例如,刺瘿螨属(Aculus spp.)的佛氏刺瘿螨(Aculus fockeui)、苹果刺锈螨(Aculus schlechtendali);以及茶尖叶节蜱(Acaphylla theavagrans)、茶叶瘿螨(Calacarus carinatus)、葡萄缺节瘿螨(Colomerusvitis)、葡萄叶锈螨(Calepitrimerus vitis)、梨上瘿螨(Epitrimerus pyri)、菊花叶锈螨(Paraphytoptus kikus)、罗汉松副丽瘿螨(Paracalacarus podocarpi)、柑橘锈螨(Phyllocotruta citri);
(d)跗线螨科(Transonemidae)的螨,例如,跗线螨属(Tarsonemus spp.)的双叶跗线螨(Tarsonemus bilobatus)、韦氏跗线螨(Tarsonemus waitei);以及樱草植食螨(Phytonemus pallidus)、侧多食跗线螨(Polyphagotarsonemus latus);
(e)叶爪螨科(Penthaleidae)的螨:例如,叶爪螨属(Penthaleus spp.)的、白菜螨(Penthaleus erythrocephalus)、麦叶爪螨(Penthaleus major)。
〔体外寄生虫防除剂〕
本发明的体外寄生虫防除剂含有选自本发明的(杂)芳基咪唑化合物中的至少1者作为有效成分。本发明的体外寄生虫防除剂中含有的(杂)芳基咪唑化合物的量只要表现出体外寄生虫的防除效果就没有特别限制。
作为本发明的体外寄生虫防除剂的处理对象的宿主动物,可列举人、家畜哺乳动物(例如牛、马、猪、绵羊、山羊等)、实验动物(例如、小鼠、大鼠、沙鼠等)、宠物动物(例如仓鼠、豚鼠、狗、猫、马、松鼠、兔子、雪貂等)、野生和动物园的哺乳动物(猴子、狐狸、鹿、水牛等)、家禽(火鸡、鸭、鸡、鹌鹑、鹅等)、宠物鸟(鸽子、鹦鹉、鹩哥、文鸟、鹦哥、白腰文鸟、金丝雀等)等恒温动物;或者鲑鱼、鳟鱼、锦鲤等鱼类。此外,还可列举蜜蜂、锹形虫、独角仙。
本发明的体外寄生虫防除剂可以通过已知的兽医学方法(局部、口服、非口服或皮下给药)进行施用。作为该方法,可举出:通过片剂、胶囊、混入饲料等向动物口服给药的方法;通过浸渍液、栓剂、注射(肌内、皮下、静脉内、腹腔内等)等向动物给药的方法;通过喷雾、浇泼(pour on)、点涂(spot on)等将油性或水性液体制剂局部给药的方法;在树脂中混入体外寄生虫防除剂,将上述混炼物成型为项圈、耳标等合适的形状,将其佩戴在动物身上,从而局部给药的方法;等等。
体外寄生虫寄生于宿主动物、特别是恒温动物的体内和体表。详细而言,寄生在宿主动物的后背、腋下、下腹部、大腿的内侧部等而从动物获得血液或皮屑等营养源,从而得以生存。作为体外寄生虫,可举出螨类、虱类、蚤类、蚊子、角蝇、麻蝇等。以下示出可利用本发明的体外寄生虫防除剂来防除的体外寄生虫的具体例。
(1)螨类(Acari)
皮刺螨科(Dermanyssidae)的螨、巨刺螨科(Macronyssidae)的螨、厉螨科(Laelapidae)的螨、瓦螨科(Varroidae)的螨、软蜱科(Argasidae)的螨、硬蜱科(Ixodidae)的螨、痒螨科(Psoroptidae)的螨、疥螨科(Sarcoptidae)的螨、膝螨科(Knemidokoptidae)的螨、蠕形螨科(Demodixidae)的螨、恙螨科(Trombiculidae)的螨、锹形虫类等昆虫寄生性螨。
(2)虱目(Phthiraptera)
盲虱科(Haematopinidae)的虱、颚虱科(Linognathidae)的虱、短角鸟虱科(Menoponidae)的鸟虱、长角鸟虱科(Philopteridae)的鸟虱、兽鸟虱科(Trichodectidae)的鸟虱。
(3)将蚤目(Siphonaptera)
蚤科(Pulicidae)的蚤,例如,犬蚤属(Ctenocephalides spp.)的犬蚤(Ctenocephalides canis)、猫蚤(Ctenocephalides felis);
潜蚤科(Tungidae)的蚤、角叶蚤科(Ceratophyllidae)的蚤、细蚤科(Leptopsyllidae)的蚤。
(4)半翅目(Hemiptera)。
(5)双翅目(Diptera)的害虫
蚊科(Culicidae)的蚊、蚋科(Simuliidae)的蚋、蠓科(Ceratopogonidae)的蠓、虻科(Tabanidae)的虻、蝇科(Muscidae)的蝇、舌蝇科(Glossinidae)的舌蝇、麻蝇科的麻蝇、虱蝇科(Hippoboscidae)的蝇、丽蝇科(Calliphoridae)的蝇、狂蝇科(Oestridae)的蝇。
〔体内寄生虫防除或驱除剂〕
本发明的体内寄生虫防除或驱除剂含有选自本发明的(杂)芳基咪唑化合物中的至少1者作为有效成分。本发明的体内寄生虫防除或驱除剂中所含的(杂)芳基咪唑化合物的量只要表现出体内寄生虫的防除效果就没有特别限制。
作为本发明的体内寄生虫防除或驱除剂的对象的寄生虫寄生于宿主动物、特别是恒温动物、鱼类中(体内寄生虫)。作为本发明的体内寄生虫防除或驱除剂有效的宿主动物,可举出人、家畜哺乳动物(例如,牛、马、猪、绵羊、山羊等)、实验动物(例如,小鼠、大鼠、沙鼠等)、宠物动物(例如,仓鼠、豚鼠、狗、猫、马、松鼠、兔、雪貂等)、野生和动物园的哺乳动物(猴子、狐狸、鹿、水牛等)、家禽(火鸡、鸭子、鸡、鹌鹑、鹅等)、宠物鸟(鸽子、鹦鹉、鹩哥、文鸟、鹦哥、白腰文鸟、金丝雀等)等恒温动物;或者鲑鱼、鳟鱼、锦鲤等鱼类。通过防除和驱除寄生虫,能够预防或治疗寄生虫介导的寄生虫疾病。
作为防除或驱除对象的寄生虫,可举出以下的寄生虫。
(1)膨结虫目(Dioctophymatida)的线虫类
(a)膨结科(Dioctophymatidae)的肾膨结线虫:例如,膨结线虫属(Dioctophymaspp.)的肾膨结线虫(Dioctophyma renale);
(b)索氏膨结科(Soboliphymatidae)的肾膨结线虫:例如,芽结属(Soboliphymespp.)的阿贝芽结线虫(Soboliphyme abei)、巴氏芽结线虫(Soboliphyme baturini)。
(2)毛首目(Trichocephalida)的线虫类
(a)毛线虫科(Trichinellidae)的旋毛虫:例如,毛线虫属(Trichinella spp.)的旋毛虫(Trichinella spiralis);
(b)鞭虫科(Trichuridae)的鞭虫:例如,毛细线虫属(Capillaria spp.)的环首毛细线虫(Capillaria annulata)、捻转毛细线虫(Capillaria contorta)、肝毛细线虫(Capillaria hepatica)、穿孔毛细线虫(Capillaria perforans)、狐膀胱毛细线虫(Capillaria plica)、猪毛细线虫(Capillaria suis);鞭虫属(Trichuris spp.)的犬鞭虫(Trichuris vulpis)、牛鞭虫(Trichuris discolor)、羊鞭虫(Trichuris ovis)、斯氏鞭虫(Trichuris skrjabini)、猪鞭虫(Trichuris suis)。
(3)杆形线虫目(Rhabditida)的线虫类
类圆线虫科(Strongyloididae)的类圆线虫:例如,类圆线虫属(Strongyloidesspp.)的乳突类圆线虫(Strongyloides papillosus)、猫类圆线虫(Strongyloidesplaniceps)、兰氏类圆线虫(Strongyloides ransomi)、猪类圆线虫(Strongyloidessuis)、粪类圆线虫(Strongyloides stercoralis)、美国猫类圆线虫(Strongyloidestumefaciens)、鼠类圆线虫(Strongyloides ratti)。
(4)圆线虫目(Strongylida)的线虫类
钩口科(Ancylostomatidae)的钩虫:例如,钩口属(Ancylostoma spp.)的巴西钩口线虫(Ancylostoma braziliense)、犬钩虫(Ancylostoma caninum)、十二指肠钩虫(Ancylostoma duodenale)、猫钩虫(Ancylostoma tubaeforme);钩虫属(Uncinariastenocephala)的狭首钩刺线虫(Uncinaria stenocephala);仰口线虫属(Bunostomumspp.)的牛仰口线虫(Bunostomum phlebotomum)、羊仰口线虫(Bunostomumtrigonocephalum)。
(5)圆线虫目(Strongylida)的线虫类
(a)管圆线虫科(Angiostrongylidae)的线虫:例如,猫圆线虫属(Aelurostrongylus spp.)的猫圆线虫(Aelurostrongylus abstrusus);血管圆线虫属(Angiostrongylus spp.)的脉居管圆线虫(Angiostrongylus vasorum)、广州管圆线虫(Angiostrongylus cantonesis);
(b)锯体科(Crenosomatidae)的线虫:例如,环体线虫属(Crenosoma spp.)的肺毛细线虫(Crenosoma aerophila)、狐环体线虫(Crenosoma vulpis);
(c)类丝虫科(Filaroididae)的线虫:例如,类丝虫属(Filaroides spp.)的犬肺虫(Filaroides hirthi)、奥氏似丝线虫(Filaroides osleri);
(d)后圆线虫科(Metastrongylidae)的肺蠕虫:例如,后圆线虫属(Metastrongylus spp.)的猪圆线虫(Metastrongylus apri)、不对称后圆线虫(Metastrongylus asymmetricus)、复阴后圆形线虫(Metastrongylus pudendotectus)、萨氏后圆线虫(Metastrongylus salmi);
(e)比翼科(Syngamidae)的开嘴虫:例如,杯口线虫属(Cyathostoma spp.)的支气管杯口线虫(Cyathostoma bronchialis);比翼线虫属(Syngamus spp.)的斯氏比翼线虫(Syngamus skrjabinomorpha)、气管比翼线虫(Syngamus trachea)。
(6)圆形目(Strongylida)的线虫类
(a)莫林线虫科(Molineidae)的线虫:例如,细颈线虫属(Nematodirus spp.)的尖刺细颈线虫(Nematodirus filicollis)、钝刺细颈线虫(Nematodirus spathiger);
(b)网尾科(Dictyocaulidae)的线虫:例如,网尾属(Dictyocaulus spp.)的丝圆线虫(Dictyocaulus filaria)、胎生网尾线虫(Dictyocaulus viviparus);
(c)捻转血矛线虫科(Haemonchidae)的线虫:例如,血矛线虫属(Haemonchusspp.)的捻转血矛线虫(Haemonchus contortus);长刺属(Mecistocirrus spp.)的指形长刺线虫(Mecistocirrus digitatus);
(d)捻转胃虫科(Haemonchidae)的线虫:例如,奥斯脱线虫属(Ostertagia spp.)的奥斯特线虫(Ostertagia ostertagi);
(e)单绕线虫科(Heligmonellidae)的线虫,例如,钩虫属(Nippostrongylusspp.)的巴西日圆线虫(Nippostrongylus braziliensis);
(f)毛圆线虫科(Trichostrongylidae)的线虫:例如,毛圆线虫属(Trichostrongylus spp.)的艾氏毛圆线虫(Trichostrongylus axei)、蛇形毛圆线虫(Trichostrongylus colubriformis)、微细毛圆线虫(Trichostrongylus tenuis);猪圆属(Hyostrongylus spp.)的红色猪圆线虫(Hyostrongylus rubidus);尖柱线虫属(Obeliscoides spp.)的兔尖柱线虫(Obeliscoides cuniculi)。
(7)圆形目(Strongylida)的线虫类
(a)夏柏特科(Chabertiidae)的线虫:例如,夏伯特属(Chabertia spp.)的绵羊夏柏特线虫(Chabertia ovina);结节线虫属(Oesophagostomum spp.)的短尾结节线虫(Oesophagostomum brevicaudatum)、哥伦比亚结节线虫(Oesophagostomumcolumbianum)、有齿结节线虫(Oesophagostomum dentatum)、佐治亚食管口线虫(Oesophagostomumgeorgianum)、梅普尔斯通结节线虫(Oesophagostomum maplestonei)、四棘食道口线虫(Oesophagostomum quadrispinulatum)、辐射食道口线虫(Oesophagostomum radiatum)、微管结节线虫(Oesophagostomum venulosum)、华氏食道口线虫(Oesophagostomumwatanabei);
(b)肾线科(Stephanuridae)的线虫:例如,冠线虫属(Stephanurus spp.)的有齿冠尾线虫(Stephanurus dentatus);
(c)圆线虫科(Strongylidae)的线虫:例如,圆线虫属(Strongylus spp.)的,驴圆形线虫(Strongylus asini)、无齿圆形线虫(Strongylus edentatus)、马圆线虫(Strongylus equinus)、寻常圆线虫(Strongylus vulgaris)。
(8)尖尾目(Oxyurida)的线虫类
尖尾科(Oxyuridae)的线虫;例如,蛲虫属(Enterobius spp.)的黑猩猩蛲虫(Enterobius anthropopitheci)、蛲虫(Enterobius vermicularis);尖尾线虫属(Oxyurisspp.)的马尖尾线虫(Oxyuris equi);栓尾属(Passalurus spp.)的兔栓尾线虫(Passalurus ambiguus)。
(9)蛔虫目(Ascaridida)的线虫类
(a)禽蛔科科(Ascaridiidae)的线虫:例如,鸡蛔虫属(Ascaridia spp.)的鸡蛔虫(Ascaridia galli);
(b)异刺科(Heterakidae)的线虫:例如,异刺属(Heterakis spp.)的贝兰渡异刺线虫(Heterakis beramporia)、短刺异刺线虫(Heterakis brevispiculum)、鸡异刺线虫(Heterakis gallinarum)、小鸡异刺线虫(Heterakis pusilla)、南方异刺线虫(Heterakisputaustralis);
(c)异尖科(Anisakidae)的线虫:例如,异尖线虫属(Anisakis spp.)的单一异尖线虫(Anisakis simplex);
(d)蛔虫科(Ascarididae)的线虫:例如,蛔虫属(Ascaris spp.)的似蚓蛔线虫(Ascaris lumbricoides)、猪蛔虫(Ascaris suum);副蛔虫属(Parascaris spp.)的马蛔虫(Parascaris equorum);
(e)弓首科(Toxocaridae)的线虫:例如,弓首属(Toxocara spp.)的犬蛔虫(Toxocara canis)、犬小蛔虫(Toxocara leonina)、猪蛔虫(Toxocarasuum)、牛蛔虫(Toxocara vitulorum)、猫蛔虫(Toxocara cati)。
(10)旋尾目(Spirurida)的线虫类
(a)蟠尾丝虫科(Onchocercidae)的线虫:例如,布鲁线虫属(Brugia spp.)的马来布鲁线虫(Brugia malayi)、彭亨布鲁线虫(Brugia pahangi)、派特布鲁丝虫(Brugiapatei);棘唇线虫属(Dipetalonema spp.)的隐蔽棘唇线虫(Dipetalonema reconditum);恶丝虫属(Dirofilaria spp.)的犬恶丝虫(Dirofilaria immitis);丝虫属(Filariaspp.)的罗阿丝虫(Filaria oculi);盘尾属(Onchocerca spp.)的马颈盘尾丝虫(Onchocerca cervicalis)、氏盘尾丝虫(Onchocerca gibsoni)、喉瘤盘尾丝虫(Onchocerca gutturosa);
(b)丝状科(Setariidae)的线虫:例如,丝虫属(Setaria spp.)的指状丝状虫(Setaria digitata)、马腹腔丝虫(Setaria equina)、牛腹腔唇乳突丝虫(Setarialabiatopapillosa)、马氏丝虫(Setaria marshalli)、吴策线虫属(Wuchereria spp.)的班氏线虫(Wuchereria bancrofti);
(c)丝虫科(Filariidae)的线虫:例如,副丝虫属(Parafilaria spp.)的多乳突副丝虫(Parafilaria multipapillosa);冠丝虫属(Stephanofilaria spp.)的阿萨麦冠丝虫(Stephanofilaria assamensis)、德氏冠丝虫(Stephanofilaria dedoesi)、咖氏冠丝虫(Stephanofilaria kaeli)、冲绳丝虫(Stephanofilaria okinawaensis)、斯氏冠丝虫(Stephanofilaria stilesi)。
(11)旋尾目(Spirurida)的线虫类
(a)颚口科(Gnathostomatidae)的线虫:例如,颚口线虫属(Gnathostoma spp.)的多氏棘颚口线虫(Gnathostoma doloresi)、陶氏颚口线虫(Gnathostoma spinigerum);
(b)柔线科(Habronematidae)的线虫:例如,丽线虫属(Habronema spp.)的大柔线虫(Habronema majus)、小口柔线虫(Habronema microstoma)、蝇柔线虫(Habronemamuscae);德拉希线虫属(Draschia spp.)的大口德拉希线虫(Draschia megastoma);
(c)泡翼科(Physalopteridae)的线虫:例如,泡翼线虫属(Physaloptera spp.)的犬泡翼线虫(Physaloptera canis)、狐狸胃虫(Physaloptera cesticillata)、泡翼线虫(Physaloptera erdocyona)、猫胃虫(Physaloptera felidis)、埃及猫胃虫(Physalopteragemina)、高加索泡翼线虫(Physaloptera papilloradiata)、包皮泡翼线虫(Physalopterapraeputialis)、Physaloptera pseudopraerutialis、稀泡翼线虫(Physaloptera rara)、西伯利亚泡翼线虫(Physaloptera sibirica)、Physaloptera vulpineus;
(d)筒线科(Gongylonematidae)的线虫:例如,筒线属(Gongylonema spp.)的美丽筒线虫(Gongylonema pulchrum);
(e)尾旋科(Spirocercidae)的线虫:例如,斜环咽线虫属(Ascarops spp.)的圆形蛔状线虫(Ascarops strongylina);
(f)吸吮科(Thelaziidae)的线虫:例如,吸吮属(Thelazia spp.)的丽嫩吸吮线(Thelazia callipaeda)、大口结膜吸吮线虫(Thelazia gulosa)、泪管吸吮线虫(Thelazialacrymalis)、露德西吸吮线虫(Thelazia rhodesi)、斯氏吸吮线虫(Thelaziaskrjabini)。
〔其它有害生物的防除剂〕
此外,本发明的(杂)芳基咪唑化合物对具有毒针或毒液而对人畜有害的害虫、传播各种病原体、病原菌的害虫、给人带来不舒服感的害虫(有毒害虫、卫生害虫、令人不舒服的害虫等)的防除效果也优异。
以下示出其具体例。
(1)膜翅目(Hymenoptera)的害虫
三节叶蜂科(Argidae)的蜂、瘿蜂科(Cynipidae)的蜂、松叶蜂科(Diprionidae)的蜂、蚁科(Formicidae)的蚂蚁、蚁蜂科(Mutillidae)的蜂、胡蜂科(Vespidae)的蜂。
(2)其它害虫
蟑螂类(Blattodea)、白蚁类(termite)、蜘蛛类(Araneae)、蜈蚣类(cetipede)、马陆类(millipede)、甲壳类(crustacea)、温带臭虫(Cimex lectularius)。
〔种子处理剂或营养繁殖器官处理剂〕
本发明的种子处理剂或营养繁殖器官处理剂含有选自本发明的(杂)芳基咪唑化合物中的至少1者作为有效成分。本发明的种子处理剂或营养繁殖器官处理剂中含有的(杂)芳基咪唑化合物的量只要表现出防除效果就没有特别限制。
营养繁殖器官是指在植物的根、茎、叶等中将该部位从主体上切去而放置于土壤时具有生长能力的器官。作为营养繁殖器官,例如,可举出块根(tuberous root)、匍匐根(creeping root)、鳞茎(bulb)、球茎(corm或solid bulb)、块茎(tuber)、根茎(rhizome)、匍匐枝(stolon)、根托(rhizophore)、插条(cane cuttings)、繁殖枝(propagule)和插枝(vine cutting)。应予说明,匍匐枝有时也被称为走茎(runner),繁殖枝也被称为珠芽,可分为肉芽(broad bud)、鳞芽(bulbil)。插枝是指红薯或山药等的苗芽(叶和茎的通称,shoot)。也将鳞茎、球茎、块茎、根茎、插条、根托或块根统称为球根。例如,薯类的栽培通过将块茎种植于土壤而开始,使用的块茎一般被称为种薯。
本发明的种子处理剂或营养繁殖器官处理剂是指:以选自本发明的(杂)芳基咪唑化合物中的至少一者作为有效成分,混合适当的固体载体或液体载体,再根据需要添加表面活性剂、其他制剂用辅助剂,制成可湿性粉剂、颗粒可湿性粉剂、混悬剂或粉剂等的制剂。另外,本组合物可以含有粘合剂。作为含有粘合剂的本组合物,可列举种子处理专用的混悬剂(FS:Flowable concentrate for seed treatment)。
作为前述粘合剂,可使用对植物种子或营养繁殖器官无植物毒性影响的粘接性物质。具体而言,可使用选自由聚乙酸乙烯酯、聚乙烯醇、包含乙基纤维素、甲基纤维素、羟甲基纤维素、羟丙基纤维素及羧甲基纤维素的纤维素、聚乙烯基吡咯烷酮、包含淀粉、改性淀粉、糊精、麦芽糊精、海藻酸盐及脱乙酰壳多糖的多糖类、包含明胶及玉米蛋白的蛋白、阿拉伯胶、虫胶、木质素磺酸钙以及甲基丙烯酰胺单体组成的组中的至少1种。
通过对种芋施用选自本发明的(杂)芳基咪唑化合物中的至少一者,从而可有效地防除有害生物。作为对种芋施用(杂)芳基咪唑化合物的方法,可列举浸渍处理、粉衣处理或包衣处理等。另外,在用拖拉机种植种芋时,也可通过在拖拉机上喷洒含有(杂)芳基咪唑化合物的药液来对种芋进行处理。
〔水稻育苗箱处理用农药粒状组合物〕
本发明的水稻育苗箱处理用农药粒状组合物(以下称作“农药粒状组合物”)含有选自本发明的(杂)芳基咪唑化合物中的至少一者作为有效成分。本发明的农药粒状组合物中所含的(杂)芳基咪唑化合物的量只要显示防除效果,就没有特别限制。
农药粒状组合物可利用各种方法来得到,例如可通过将配合有1种以上的有效成分、和根据需要的表面活性剂、粘合剂及无机载体等的粉状组合物利用湿式造粒法进行挤出、造粒等来得到。更具体而言,将调整为规定粒度的有效成分和所需的表面活性剂、粘合剂及无机载体均匀混合后,添加适量的水,进行混炼,由开设有细孔的筛网进行挤出,再进行成型、干燥,制成农药粒状组合物。此时使用的细孔的大小通常优选为0.5mm~1.5mm。
如上述那样得到的农药粒状组合物的粒径并无特别限制,但平均粒径优选为0.5mm~1.5mm,特别优选为0.7mm~1.5mm。这样的粒径的造粒粒状物可通过造粒、干燥后筛分来得到。
农药粒状组合物可根据需要配合表面活性剂、粘合剂及无机载体。其中,作为表面活性剂,可列举例如:聚乙二醇高级脂肪酸酯、聚氧乙烯烷基醚、聚氧乙烯烷基芳基醚、聚氧乙烯芳基苯基醚、山梨糖醇酐单烷基化物等非离子性表面活性剂;烷基芳基磺酸盐、二烷基磺酸盐、烷基硫酸酯盐、烷基磷酸酯盐、烷基芳基硫酸酯盐、烷基芳基磷酸酯盐、聚氧乙烯烷基醚硫酸酯盐、萘磺酸盐及其缩合物、木质素磺酸盐、丙烯酸与衣康酸的共聚物或者甲基丙烯酸与衣康酸的共聚物、马来酸与苯乙烯的共聚物、马来酸与二异丁烯的共聚物及它们的碱金属盐等多元羧酸型高分子活性剂;聚氧乙烯芳基苯基醚磷酸酯盐;聚氧乙烯芳基苯基醚硫酸酯盐等阴离子性表面活性剂等。该表面活性剂的配合量通常为0.1重量份~5重量份,但并无特别限定。
作为在农药粒状组合物中配合的粘合剂,可列举例如羧甲基纤维素金属盐、聚乙烯醇、α化淀粉、糊精、黄原胶、瓜尔豆胶、蔗糖、聚乙烯基吡咯烷酮、聚丙烯酸金属盐等,通常所配合的量为0.1重量份~5重量份,但并无特别限定。而且,作为在造粒粒状物中配合的无机载体,并无特别限定,可列举例如粘土类、碳酸钙、滑石、硅藻土、沸石、绿坡缕石、石膏、陶石等。
〔土壤处理剂〕
本发明中的土壤处理是指例如下述方法:通过对要保护而免受有害生物摄食等侵害的植物的根区施用有效成分,从而直接防除有害生物,或者使有效成分从根部等渗透转移至植物体内部而防除有害生物。具体而言,可列举例如:植穴处理(植穴散布、植穴处理土壤混合)、植株根部处理(植株根部散布、植株根部土壤混合、植株根部灌注、育苗期后半植株根部处理)、植沟处理(植沟散布、植沟土壤混合)、播种沟处理(播种沟散布、播种沟土壤混合、生育期播种沟散布)、播种时播种沟处理(播种时播种沟散布、播种时播种沟土壤混合)、全面处理(全面土壤散布、全面土壤混合)、垄处理、水面处理(全面水面施用、边缘水面施用)、其他土壤散布处理(生育期粒剂叶面散布、树冠下或主干周边散布、土壤表面散布、土壤表面混合、播穴散布、畦部地表面散布、株间散布)、其他灌注处理(土壤灌注、育苗期灌注、药液注入处理、贴近地面部灌注、药液滴灌、化学灌溉)、育苗箱处理(育苗箱散布、育苗箱灌注、育苗箱药液湛水)苗床处理(苗床散布、苗床灌注、水秧田苗床散布)、苗浸渍、育苗培土混合处理(床土混合、覆土混合)、播种时覆土前散布、播种时覆土后散布、茎注入处理、树干注入处理、树干散布处理、其他处理(锄入、表土混合、雨水滴落部混合、栽植位置处理、粒剂花萼散布、糊状肥料混合)。
〔饵剂〕
本发明的饵剂含有选自本发明的(杂)芳基咪唑化合物中的至少一者作为有效成分。本发明的饵剂中所含的(杂)芳基咪唑化合物的量只要显示防除效果,就没有特别限制。
本发明的饵剂可根据需要含有糖、碳水化合物、乳成分等摄取性提高成分、增效剂、防误食剂、保存剂、香料、诱引剂等。本发明的饵剂通常可通过混合(杂)芳基咪唑化合物及水、根据需要的上述其他成分混合来调整。在本发明的饵剂的调整中,(杂)芳基咪唑化合物可以是(杂)芳基咪唑化合物本身,也可以是粉剂、可湿性粉剂、微囊剂、混悬剂等制剂形态。
作为可通过本发明的饵剂来有效地防除的有害生物,可列举:美洲大蠊(Peliplaneta americana)、德国小蠊(blattella germanica)、黑胸大蠊(Periplanetafuliginosa)等蜚蠊;Melanotus okinawensis等叩甲;黑腹小家蚁(Monomoriumintrudens)、日本黑褐蚁(Formica japonica)等蚁;烟草甲(Lasioderma serricorne)、药材甲(drugstore beetle)等窃蠹;面象虫(flour beetle)、杂拟谷盗(confused flourbeetle)等面象虫;锯谷盗(Oryzaephilus surinamensis)、锈赤扁谷盗(Cryptolestesferrugineus Stephens)等扁甲;家白蚁(Coptotermes formosanus)、栖北散白蚁(Reticulitermes speratus)等的蚁、家蝇、黄腹厕蝇(Fannia canicularis)、蚤蝇科、白蛉亚科科等蝇、尖音库蚊(culex pipiens)、白纹伊蚊(Aedes albopictus)、疟蚊(anopheles)、摇蚊(chironomid)等蚊。
作为本发明的饵剂的施用形态,可以直接是本发明的饵剂的状态,也可以是含浸于例如无纺布、海绵、脱脂棉等的状态。本水性饵剂、含浸有本饵剂的无纺布、海绵、脱脂棉等被放入例如杯、托盘、瓶等容器而供于害虫驱除。此时,如果制成覆盖装有本发明的饵剂的容器的外侧、具有可供害虫停留以摄取本发明的饵剂的一定程度空间的装置,则通常摄取性提高,是有效的。
〔植物生长促进剂〕
本发明的植物生长促进剂含有选自本发明的(杂)芳基咪唑化合物中的至少1者作为有效成分。本发明的植物生长促进剂中含有的(杂)芳基咪唑化合物的量只要呈现出植物生长促进效果就没有特别限制。
本发明的植物生长促进剂可以根据需要适当配合其他成分、载体等。
本发明的(杂)芳基咪唑化合物也能单独作为植物生长促进剂来使用,但通常可与以(杂)芳基咪唑化合物为有效成分的制剂中所使用的惯用的固体载体、液体载体、分散剂、稀释剂、乳化剂、展着剂及增稠剂等辅助剂混合而制成可湿性粉剂、液剂、油剂、粉剂、粒剂或溶胶剂(混悬剂)等剂型来使用。
作为固体载体或液体载体,可列举例如滑石、粘土、膨润土、高岭土、硅藻土、蒙脱石、云母、蛭石、石膏、碳酸钙、白炭、木粉、淀粉、氧化铝、硅酸盐、糖聚合物、蜡类、水、醇类(甲醇、乙醇、正丙醇、异丙醇、正丁醇、乙二醇、苄醇等)、石油溜分(石油醚、煤油、溶剂石脑油等)、脂肪族或脂环式烃类(正己烷、环己烷等)、芳香族烃类(苯、甲苯、二甲苯、乙基苯、氯苯、异丙苯、甲基萘等)、卤代烃类(氯仿、二氯甲烷等)、醚类(异丙基醚、环氧乙烷、四氢呋喃等)、酮类(丙酮、甲乙酮、环己酮、甲基异丁基酮等)、酯类(乙酸乙酯、乙酸丁酯、乙二醇乙酸酯、乙酸戊酯等)、酰胺类(二甲基甲酰胺、二甲基乙酰苯胺等)、腈类(乙腈、丙腈、丙烯腈等)、亚砜类(二甲基亚砜等)、醇醚类(乙二醇单甲基醚、乙二醇单乙基醚等)等。
作为辅助剂,可列举例如非离子型表面活性剂(聚氧乙烯烷基醚、聚氧乙烯烷基酯、聚氧乙烯烷基苯基醚、聚氧乙烯山梨糖醇酐烷基酯、山梨糖醇酐烷基酯等)、阴离子型表面活性剂(烷基苯磺酸酯、烷基磺基丁二酸酯、聚氧乙烯烷基硫酸酯、芳基磺酸酯等)、阳离子型表面活性剂(烷基胺类、聚氧乙烯烷基胺类、季铵盐类等)、两性型表面活性剂(烷基氨基乙基甘氨酸、烷基二甲基甜菜碱等)、聚乙烯醇、羟丙基纤维素、羧甲基纤维素、阿拉伯胶、黄蓍胶、黄原胶、聚乙酸乙烯基酯、明胶、酪朊、海藻酸钠等。
作为其他成分,可列举:前述的杀菌剂、杀虫·杀螨剂、杀线虫剂、杀土壤害虫剂等其他有效成分;植物调节剂、增效剂、肥料、土壤改良剂、动物用饲料等。
本发明的(杂)芳基咪唑化合物在植物生长促进剂中的含量根据制剂形态、施用方法、其他条件而各不相同,但优选为0.5~95重量%,特别优选为2~70重量%的范围。
就作为应用对象的植物而言,并无特别限定,可列举:例如水稻、大麦、小麦、稗子、玉米、谷子等禾本科的谷物类;南瓜、芜菁、卷心菜、萝卜、白菜、菠菜、青椒、番茄等蔬菜类;菊花、非洲菊、三色堇(pansy)、兰、芍药、郁金香等花卉类;小豆、扁豆、大豆、花生、蚕豆、豌豆等豆类;马铃薯、甘薯、香芋、山芋、芋头等薯类;葱、洋葱、薤等葱类等。
作为本发明的植物生长促进剂的施用方法,可以为对植物的施用(茎叶散布)、对植物的生长土壤的施用(土壤施用)、对田面水的施用(水面施用)、对种子的施用(种子处理)等。
关于本发明的植物生长促进剂的施用量,根据应用植物等不同也不同,但在茎叶散布的情况下,作为有效成分浓度,优选的是每10公亩施用1~10000ppm的范围、优选10~1000ppm的溶液50~300L,在土壤施用及水面施用的情况下,优选的是每10公亩以有效成分量计施用0.1~1000g、特别优选10~100g。另外,在种子处理的情况下,优选对种子1Kg施用0.001~50g的有效成分。
〔制剂处方〕
虽然示出若干本发明的有害生物防除剂、杀虫或杀螨剂、体外寄生虫防除剂或体内寄生虫防除或驱除剂的制剂处方,但添加物及添加比例不应受这些实施例限定,可使其在较广范围内进行变化。制剂处方中的份表示重量份。
以下示出农业园艺用和水稻用的制剂处方。
(制剂1:可湿性粉剂)
将本发明的(杂)芳基咪唑化合物40份、硅藻土53份、高级醇硫酸酯4份及烷基萘磺酸盐3份均匀混合并微细地粉碎,得到有效成分为40%的可湿性粉剂。
(制剂2:乳剂)
将本发明的(杂)芳基咪唑化合物30份、二甲苯33份、二甲基甲酰胺30份及聚氧乙烯烷基烯丙基醚7份混合溶解,得到有效成分为30%的乳剂。
(制剂3:粒剂)
将本发明的(杂)芳基咪唑化合物5份、滑石40份、粘土38份、膨润土10份及烷基硫酸钠7份均匀混合并微细地粉碎后,造粒成直径0.5~1.0mm的粒状,得到有效成分为5%的粒剂。
(制剂4:粒剂)
将本发明的(杂)芳基咪唑化合物5份、粘土73份、膨润土20份、琥珀酸二辛酯磺酸钠盐1份及磷酸钾1份充分粉碎混合,加入水并使其充分混炼,然后进行造粒干燥,得到有效成分为5%的粒剂。
(制剂5:悬浊剂)
将本发明的(杂)芳基咪唑化合物10份、聚氧乙烯烷基烯丙基醚4份、聚羧酸钠盐2份、甘油10份、黄原胶0.2份及水73.8份混合,湿式粉碎至粒度为3微米以下,得到有效成分为10%的悬浊剂。
以下示出体外寄生虫防除剂、或者体内寄生虫防除或驱除剂的制剂处方。
(制剂6:颗粒剂)
使本发明的(杂)芳基咪唑化合物5份溶解在有机溶剂中而得到溶液,将该溶液喷雾到高岭土94份及白炭1份上,接着,使溶剂在减压下蒸发。这种颗粒可以与动物的饵料混合。
(制剂7:注入剂)
将本发明的(杂)芳基咪唑化合物0.1~1份与花生油99~99.9份均匀混合,接着,利用灭菌过滤器进行过滤灭菌。
(制剂8:浇泼(pour-on)剂)
将本发明的(杂)芳基咪唑化合物5份、肉豆蔻酸酯10份及异丙醇85份均匀混合而得到浇泼剂。
(制剂9:喷滴(spot on)剂)
将本发明的(杂)芳基咪唑化合物10~15份、棕榈酸酯10份及异丙醇75~80份均匀混合而得到喷滴剂。
(制剂10:喷雾剂)
将本发明的(杂)芳基咪唑化合物1份、丙二醇10份及异丙醇89份均匀混合而得到喷雾剂。
接着,示出化合物实施例而对本发明进行更具体的说明。但是,本发明不受以下的化合物实施例的任何限制。
〔实施例1〕
2-(5-(2-氯-3,3,3-三氟丙-1-烯-1-基)-1-甲基-1H-咪唑-2-基)-5-环丙基-3-(乙基磺酰基)吡啶〔2-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-5-cyclopropyl-3-(ethylsulfonyl)pyridine〕(化合物编号d-2)的合成
(工序1)5-溴-3-(乙基硫基)氰基吡啶〔5-bromo-3-(ethylthio)picolinonitrile〕的合成
[化学式34]
在反应容器中,将5-溴-3-硝基氰基吡啶(1g)溶解于四氢呋喃(22ml),对该反应容器进行氮气置换。然后,冷却至-5℃并进行搅拌。向其中加入ca.60%氢化钠(0.2g),于-5℃搅拌5分钟。接着,滴加乙硫醇(0.27g),于-5℃搅拌30分钟。将得到的液体注入水中,用乙酸乙酯进行萃取。将得到的有机层用饱和食盐水进行清洗,用无水硫酸镁干燥并进行过滤。对滤液进行减压浓缩。将得到的浓缩物用硅胶柱色谱进行纯化,由此得到目标物0.90g(收率84%)。
将得到的目标物的1H-NMR示于以下。
1H-NMR(CDCl3)δ:8.50(1H,d),7.83(1H,d),3.07(2H,q),1.41(3H,t).
(工序2)5-溴-3-(乙基磺酰基)氰基吡啶〔5-bromo-3-(ethylsulfonyl)picolinonitrile〕的合成
[化学式35]
将5-溴-3-(乙基硫基)氰基吡啶(149g)溶解于二氯甲烷(1800ml),冷却至0℃并进行搅拌。向其中加入70%间氯过氧苯甲酸(333g),于室温搅拌一夜。将得到的液体注入饱和碳酸氢钠水溶液与饱和硫代硫酸钠水溶液的混合溶液,用二氯甲烷进行萃取。将得到的有机层用饱和食盐水清洗,用无水硫酸镁干燥并进行过滤。对滤液进行减压浓缩。将得到的浓缩物用硅胶柱色谱进行纯化,由此得到目标物167g(收率99%)。
将得到的目标物的1H-NMR示于以下。
1H-NMR(CDCl3)δ:9.26(1H,d),8.72(1H,d),3.60(2H,q),1.23(3H,t).
(工序3)2-(5-溴-3-(乙基磺酰基)吡啶-2-基)-1-甲基-1H-咪唑-5-甲醛〔2-(5-bromo-3-(ethylsulfonyl)pyridin-2-yl)-1-methyl-1H-imidazole-5-carbaldehyde〕的合成
[化学式36]
将5-溴-3-(乙基磺酰基)氰基吡啶(20g)溶解于甲醇(220ml),滴加ca.5M甲醇钠甲醇溶液(1.5ml),于室温搅拌一夜。向其中加入甲基胺盐酸盐(4.9g),加热回流下搅拌2小时。向其中加入三乙基胺(30ml),得到溶液A。
另外,将5-溴丙二醛(16.5g)与异丙醇(220ml)混合,于50℃搅拌1小时,得到溶液B。
将溶液B滴加到溶液A中,在加热回流下搅拌4小时。对得到的液体进行减压浓缩。向得到的残渣中加入水,用乙酸乙酯进行萃取。将得到的有机层用饱和食盐水清洗,用无水硫酸镁干燥并进行过滤。对滤液进行减压浓缩。将得到的浓缩物用硅胶柱色谱进行纯化,由此得到目标物12g(收率46%)。
将得到的目标物的1H-NMR示于以下。
1H-NMR(CDCl3)δ:9.86(1H,s),9.00(1H,d),8.62(1H,d),7.83(1H,s),3.89(3H,s),3.79(2H,q),1.36(3H,t).
(工序4)2-(5-环丙基-3-(乙基磺酰基)吡啶-2-基)-1-甲基-1H-咪唑-5-甲醛〔2-(5-cyclopropyl-3-(ethylsulfonyl)pyridin-2-yl)-1-methyl-1H-imidazole-5-carbaldehyde〕的合成
[化学式37]
在反应容器中,将2-(5-溴-3-(乙基磺酰基)吡啶-2-基)-1-甲基-1H-咪唑-5-甲醛(0.35g)溶解于二甲苯(4.3ml),对反应容器进行氩气置换。之后,于室温进行搅拌。向其中加入环丙基三氟硼酸钾(0.36g)、乙酸钯(II)(0.043g)、20%三环己基膦甲苯溶液(0.54g)、磷酸三钾(0.82g)及水(0.48ml),于110℃搅拌7小时。将得到的液体注入水中,用乙酸乙酯进行萃取。将得到的有机层用饱和食盐水清洗,用无水硫酸镁干燥并进行过滤。对滤液进行减压浓缩。将得到的浓缩物用硅胶柱色谱进行纯化,由此得到目标物0.27g(收率88%)。
将得到的目标物的1H-NMR示于以下。
1H-NMR(CDCl3)δ:9.84(1H,s),8.70(1H,d),8.02(1H,d),7.82(1H,s),3.84(3H,s),3.70(2H,q),2.12-2.06(1H,m),1.31(3H,t),1.28-1.23(2H,m),0.95-0.91(2H,m).
(工序5)2-(5-(2-氯-3,3,3-三氟丙-1-烯-1-基)-1-甲基-1H-咪唑-2-基)-5-环丙基-3-(乙基磺酰基)吡啶〔2-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-5-cyclopropyl-3-(ethylsulfonyl)pyridine〕的合成
[化学式38]
在反应容器中,将2-(5-环丙基-3-(乙基磺酰基)吡啶-2-基)-1-甲基-1H-咪唑-5-甲醛(0.3g)溶解于N,N-二甲基甲酰胺(13ml),于室温进行搅拌。向其中加入1,1,1-三氯-2,2,2-三氟乙烷(0.35g)、锌粉(0.31g)、乙酸酐(0.14g)及氯化铜(4.7mg),对反应容器内进行氩气置换,于60℃搅拌一夜。将得到的液体注入10%罗谢尔盐水溶液中,用乙酸乙酯进行萃取。将得到的有机层用饱和食盐水清洗,用无水硫酸镁干燥并进行过滤。对滤液进行减压浓缩。将得到的浓缩物用硅胶柱色谱进行纯化,由此得到目标物0.23g(E/Z=17:83,收率59%)。
将得到的目标物的1H-NMR及19F-NMR示于以下。
1H-NMR(400MHz,CDCl3)(E/Z混合物)δ:8.68(1H,d),8.04(1H,s),8.02(1H,d),7.15(1H,s),3.74(2H,q),3.57(3H,s),2.12-2.06(1H,m),1.31(3H,t),1.28-1.20(2H,m),0.94-0.89(2H,m);19F-NMR(376MHz,CDCl3-C6F6):(E)-异构体为δ-63.5(d),(Z)-异构体为-68.4(s).
〔实施例2〕
1-(6-(5-(2-氯-3,3,3-三氟丙-1-烯-1-基)-1-甲基-1H-咪唑-2-基)-5-(乙基磺酰基)吡啶-3-基)环丙烷-1-甲腈〔1-(6-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-5-(ethylsulfonyl)pyridin-3-yl)cyclopropane-1-carbonitrile〕(化合物编号d-15)的合成
(工序1)2-(5-(1,3-二氧戊环-2-基)-1-甲基-1H-咪唑-2-基)-5-溴-3-(乙基磺酰基)吡啶〔2-(5-(1,3-dioxolan-2-yl)-1-methyl-1H-imidazol-2-yl)-5-bromo-3-(ethylsulfonyl)pyridine〕的合成
[化学式39]
将2-(5-溴-3-(乙基磺酰基)吡啶-2-基)-1-甲基-1H-咪唑-5-甲醛(8.0g)溶解于甲苯(150ml),于室温进行搅拌。向其中加入乙二醇(17g)及对甲苯磺酸一水合物(0.84g),使用迪安-斯塔克装置在加热回流下搅拌一夜。将得到的液体注入饱和碳酸氢钠水溶液,用氯仿进行萃取。将得到的有机层用饱和食盐水清洗,用无水硫酸镁干燥并进行过滤。对滤液进行减压浓缩。将得到的浓缩物用硅胶柱色谱进行纯化,由此得到目标物8.5g(收率96%)。
将得到的目标物的1H-NMR示于以下。
1H-NMR(CDCl3)δ:8.94(1H,d),8.60(1H,d),7.19(1H,s),6.02(1H,s),4.17-4.00(4H,m),3.86(2H,q),3.64(3H,s),1.33(3H,t).
(工序2)2-(6-(5-(1,3-二氧戊环-2-基)-1-甲基-1H-咪唑-2-基)-5-(乙基磺酰基)吡啶-3-基)乙腈〔2-(6-(5-(1,3-dioxolan-2-yl)-1-methyl-1H-imidazol-2-yl)-5-(ethylsulfonyl)pyridin-3-yl)acetonitrile〕的合成
[化学式40]
在反应溶液中,使2-(5-(1,3-二氧戊环-2-基)-1-甲基-1H-咪唑-2-基)-5-溴-3-(乙基磺酰基)吡啶(1.75g)溶解于N,N-二甲基甲酰胺(23ml),对反应容器进行氩气置换。之后,于室温进行搅拌。向其中加入三甲基甲硅烷基乙腈(0.98g)、三(二亚苄基丙酮)二钯(0)(0.40g)、4,5-双(二苯基膦)-9,9-二甲基氧杂蒽(0.50g)及氟化锌(0.27g),于100℃搅拌3小时。将得到的液体注入饱和氯化铵水溶液,用乙酸乙酯进行萃取。将得到的有机层用饱和食盐水清洗,用无水硫酸镁干燥并进行过滤。对滤液进行减压浓缩。将得到的浓缩物用硅胶柱色谱进行纯化,由此得到目标物0.51g(收率42%)。
将得到的目标物的1H-NMR示于以下。
1H-NMR(CDCl3)δ:8.98-8.87(1H,m),8.46-8.39(1H,m),7.21(1H,s),6.03(1H,s),4.18-4.02(4H,m),3.96-3.93(2H,m),3.87(2H,q),3.65(3H,s),1.33(3H,t).
(工序3)1-(6-(5-(1,3-二氧戊环-2-基)-1-甲基-1H-咪唑-2-基)-5-(乙基磺酰基)吡啶-3-基)环丙烷-1-甲腈〔1-(6-(5-(1,3-dioxolan-2-yl)-1-methyl-1H-imidazol-2-yl)-5-(ethylsulfonyl)pyridin-3-yl)cyclopropane-1-carbonitrile〕的合成
[化学式41]
将2-(6-(5-(1,3-二氧戊环-2-基)-1-甲基-1H-咪唑-2-基)-5-(乙基磺酰基)吡啶-3-基)乙腈(0.50g)溶解于N,N-二甲基甲酰胺(5ml),于0℃进行搅拌。向其中加入碳酸铯(0.45g)。之后滴加1,2-二溴乙烷(0.52g),于0℃搅拌20分钟。向其中加入碳酸铯(0.90g),于室温搅拌3小时。将得到的液体注入水中,用乙酸乙酯进行萃取。将得到的有机层用饱和食盐水清洗,用无水硫酸镁干燥并进行过滤。对滤液进行减压浓缩。将得到的浓缩物用硅胶柱色谱进行纯化,由此得到目标物0.29g(收率54%)。
将得到的目标物的1H-NMR示于以下。
1H-NMR(CDCl3)δ:8.97(1H,d),8.17(1H,d),7.19(1H,s),6.02(1H,s),4.18-4.01(4H,m),3.85(2H,q),3.64(3H,s),1.97(2H,dd),1.61(2H,dd),1.31(3H,t).
(工序4)1-(5-(乙基磺酰基)-6-(5-甲酰基-1-甲基-1H-咪唑-2-基)吡啶-3-基)环丙烷-1-甲腈〔1-(5-(ethylsulfonyl)-6-(5-formyl-1-methyl-1H-imidazol-2-yl)pyridin-3-yl)cyclopropane-1-carbonitrile〕的合成
[化学式42]
将1-(6-(5-(1,3-二氧戊环-2-基)-1-甲基-1H-咪唑-2-基)-5-(乙基磺酰基)吡啶-3-基)环丙烷-1-甲腈(0.24g)溶解于四氢呋喃(10ml),于0℃进行搅拌。向其中加入10%盐酸(2ml),于室温搅拌3小时。将得到的液体注入饱和碳酸氢钠水溶液,用乙酸乙酯进行萃取。将得到的有机层用饱和食盐水清洗,用无水硫酸镁干燥并进行过滤。对滤液进行减压浓缩。将得到的浓缩物用硅胶柱色谱进行纯化,由此得到目标物0.23g(收率54%)。
将得到的目标物的1H-NMR示于以下。
1H-NMR(CDCl3)δ:9.86(1H,s),9.00(1H,d),8.20(1H,d),7.83(1H,s),3.88(3H,s),3.79(2H,dd),2.01(2H,dd),1.64(2H,dd),1.34(3H,t).
(工序5)1-(6-(5-(2-氯-3,3,3-三氟丙-1-烯-1-基)-1-甲基-1H-咪唑-2-基)-5-(乙基磺酰基)吡啶-3-基)环丙烷-1-甲腈〔1-(6-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-5-(ethylsulfonyl)pyridin-3-yl)cyclopropane-1-carbonitrile〕的合成
[化学式43]
在反应容器中,将1-(5-(乙基磺酰基)-6-(5-甲酰基-1-甲基-1H-咪唑-2-基)吡啶-3-基)环丙烷-1-甲腈(0.23g)溶解于N,N-二甲基甲酰胺(10ml),于室温进行搅拌。向其中加入1,1,1-三氯-2,2,2-三氟乙烷(3.1g)、锌粉(2.0g)、乙酸酐(1.0g)及氯化铜(3.0mg),对反应容器内进行氩气置换,于60℃搅拌一夜。将得到的液体注入饱和碳酸氢钠水溶液,用乙酸乙酯进行萃取。将得到的有机层用饱和食盐水清洗,用无水硫酸镁干燥并进行过滤。对滤液进行减压浓缩。将得到的浓缩物用硅胶柱色谱进行纯化,由此得到目标物0.09g(E/Z=18:82,收率30%)。
将得到的目标物的1H-NMR及19F-NMR示于以下。
1H-NMR(400MHz,CDCl3)(E/Z混合物)δ:8.99(1H,d),8.19(1H,d),8.05(1H,s),7.16(1H,s),3.85(2H,q),3.63(3H,s),2.00(2H,dd),1.63(2H,dd),1.34(3H,t);19F-NMR(376MHz,CDCl3-C6F6):(E)-异构体为δ-63.5(s),(Z)-异构体为-68.5(s).
将利用与前述的实施例同样的方法制造的本发明化合物的一部分示于表1~表2。表1示出式(I)所示的化合物的取代基。表中一并示出作为各化合物的物性的性状或熔点(m.p.)。
需要说明的是,表1中的Me表示甲基,Et表示乙基,cPr表示环丙基,cPen表示环戊基。
[化学式44]
[表1]
表1
[表2]
表2
关于表1所示的化合物中的、物性为粘性油或无定形的化合物,将1H-NMR数据示于以下。
化合物编号d-6:1H-NMR(400MHz,CDCl3):d 8.08(s,1H),7.48(s,1H),7.23(d,1H),7.15(d,1H),6.94(dd,1H),3.47(s,3H),3.42(s,3H),2.79(q,2H),1.98-1.90(m,1H),1.22(t,3H),1.21(t,3H),1.07-1.02(m,2H),0.78-0.84(m,2H).
化合物编号d-16:1H-NMR(400MHz,CDCl3):d 8.99(d,1H),8.19(d,1H),7.47(s,1H),7.05-6.98(m,1H),6.22-6.13(m,1H),3.86(q,3H),3.62(s,3H),2.01-1.97(m,2H),1.64-1.60(m,2H),1.34(t,3H).
〔生物试验〕
通过以下的试验例来示出本发明的(杂)芳基咪唑化合物作为有害生物防除剂及体外寄生虫防除剂的有效成分是有用的。需要说明的是,“份”为重量基准。
(试验用乳剂的制备)
将本发明(杂)芳基咪唑化合物5份、二甲基甲酰胺93.6份及聚氧乙烯烷基芳基醚1.4份混合溶解,制备有效成分为5%的乳剂(I)。
为了对照,将二甲基甲酰胺98.5份及聚氧乙烯烷基芳基醚1.5份混合溶解而制备乳剂(II)。
杀虫率根据下式来算出。
杀虫率(%)=(死亡虫数/供试虫数)×100
(试验例1)对粘虫的效力试验
将市售的人工饲料(Insecta LFS,日本农产工业公司制)0.8g和乳剂(I)1μl充分混合,得到试验用饲料。
在塑料制试验容器(容积1.4ml)中,对各处理区分别填装0.2g的试验用饲料。接着,对各处理区分别接种2只粘虫2龄幼虫。将塑料制的盖以不使粘虫2龄幼虫逃出的方式放置于试验容器上。将其置于25℃的恒温室内,在第5天调查了杀虫率和摄食量。试验反复进行2次。
作为对照区,将乳剂(I)变更为乳剂(II),除此以外,利用与试验例1同样的方法调查了杀虫率和摄食量。
针对化合物编号d-1、d-2、d-3、d-4、d-5、d-6、d-7、d-8、d-11、d-12、d-13、d-14、d-15、d-16、d-18、d-19、d-20、d-21、d-22、d-23、d-24、d-27、d-28、d-29、d-30、d-32、d-33、d-34、d-35、d-36、d-37、e-1及e-4的化合物,进行了对粘虫的效力试验。对于任一化合物而言,粘虫的杀虫率均为100%或摄食量以相对于对照区之比来计均为10%以下。可见本发明(杂)芳基咪唑化合物对粘虫有效。
(试验例2)对粘虫的效力试验
以使本发明化合物的浓度成为125ppm的方式将乳剂(I)用水进行稀释。将玉米叶片在前述稀释液中浸渍30秒。将该玉米叶片放入培养皿中,投放5只粘虫2龄幼虫。将培养皿置于温度25℃、湿度60%的恒温室内。在从放虫起经过6天时进行生死判定,算出杀虫率。试验反复进行2次。
针对化合物编号d-1、d-2及d-15的化合物,进行了对粘虫的效力试验。任一化合物均对粘虫显示出80%以上的杀虫率。
(试验例3)对小菜蛾的效力试验
以使本发明化合物的浓度成为125ppm的方式将乳剂(I)用水进行稀释。将卷心菜叶在前述稀释液中浸渍30秒。将该卷心菜叶放入培养皿中。向其中投放5只小菜蛾2龄幼虫。将培养皿置于温度25℃、湿度60%的恒温室内中。在从放虫起经过3天时进行生死判定,算出杀虫率。试验反复进行2次。
针对化合物编号d-1、d-2、d-4、d-7、d-9、d-10、d-12、d-13、d-15、d-18、d-20、d-21、d-22、d-23、d-24、d-25、d-26、d-27、d-28、d-29、d-30、d-31、d-33及d-34的化合物,进行对小菜蛾的效力试验。任一化合物均对小菜蛾显示出80%以上的杀虫率。
(试验例4)对斜纹夜蛾的效力试验
以使本发明化合物的浓度成为125ppm的方式将乳剂(I)用水进行稀释。将卷心菜叶在前述稀释液中浸渍30秒。将该卷心菜叶放入培养皿组中,投放5只斜纹夜蛾2龄幼虫。将培养皿置于温度25℃、湿度60%的恒温室内。在从放虫起经过6天时进行生死判定,算出杀虫率。试验反复进行2次。
针对化合物d-2、d-12及d-15的化合物,进行对斜纹夜蛾的效力试验。任一化合物均对斜纹夜蛾显示80%以上的杀虫率。
(试验例5)对豆蚜的效力试验
在3寸钵中对豇豆进行育苗,在初生叶上接种豆蚜幼虫。以使本发明化合物成为125ppm的方式将乳剂(I)用水稀释,向豆蚜幼虫寄生的豇豆中散布前述稀释液。将该豇豆置于温度25℃、湿度60%的恒温室内。在从散布起经过4天时进行豆蚜的生死判定,算出杀虫率。试验反复进行2次。
针对化合物编号d-1、d-2、d-3、d-4、d-5、d-6、d-7、d-8、d-11、d-12、d-13、d-15、d-16、d-17、d-18、d-20、d-21、d-22、d-23、d-24、d-25、d-27、d-29、d-30、d-32、d-34、d-35、d-36、d-37及e-1的化合物,进行对豆蚜的效力试验。任一化合物均对豆蚜显示80%以上的杀虫率。
(试验例6)对黄曲条跳甲的效力试验
以使本发明化合物成为125ppm的方式将乳剂(I)用水进行稀释,制备试验用药液。向种植于3寸钵的青梗菜(Brassica rapa var.chinensis)苗(第7片叶展开期)散布前述试验用药液。使青梗菜苗风干,接着,放入塑料杯中。向其中投放10只黄曲条跳甲(Phyllotreta striolata)成虫。在温度25℃、湿度65%的恒温室内保存,在从放虫起7天后进行生死判定,算出杀虫率。试验反复进行2次。
针对化合物编号d-1、d-2、d-4、d-9、d-10、d-12、d-13、d-15、d-18、d-20、d-22、d-23、d-25、d-26、d-27、d-29、d-31、d-33、d-34及e-2的化合物,进行对黄曲条跳甲成虫的效力试验。任一化合物均对黄曲条跳甲成虫显示80%以上的杀虫率。
(试验例7)对褐飞虱的效力试验
以使本发明化合物的浓度成为125ppm的方式将乳剂(I)用水进行稀释。将稻幼苗在该稀释液中浸渍30秒。使稻幼苗风干,接着,放入塑料盒中。向其中投放5只褐飞虱2龄幼虫。在温度25℃、湿度65%的恒温室内保存,在从接种起7天后进行生死判定,算出杀虫率。试验反复进行2次。
针对化合物编号d-1、d-2、d-9、d-13、d-15、d-18、d-22、d-23、d-25、d-26、d-30及d-31的化合物,进行对褐飞虱的效力试验。任一化合物均对褐飞虱显示出80%以上的杀虫率。
(试验例8)对家蝇的效力试验
将本发明化合物用丙酮稀释,将该稀释液滴到1g的方糖上,使得本发明化合物达到100ppm。将该方糖放入塑料杯中,投放10只家蝇(Musca domestica)雌成虫,改上盖子。于25℃保存,在从放虫起24小时后进行生死判定,算出杀虫率。试验反复进行2次。
针对化合物编号d-2的化合物,进行对家蝇的效力试验。任一化合物均对家蝇显示出80%以上的杀虫率。
(试验例9)对棉蚜的效力试验
将在3寸钵中育苗后的黄瓜从3寸钵中拔起,用自来水冲洗附着于根部的土壤,将根部浸渍在自来水中,进行水培。向黄瓜苗接种棉蚜幼虫。将乳剂(I)用水稀释,得到本发明化合物的浓度为31ppm的稀释液。将自来水更换为前述稀释液,在温度25℃、湿度60%的恒温室内继续用前述稀释液进行水培。从用前述稀释液开始水培起经过6天时,进行棉蚜的生死判定,算出杀虫率。试验反复进行2次。
针对化合物编号d-1、d-2、d-9、d-15、d-18、d-26、d-27及d-33的化合物,进行对棉蚜的效力试验。任一化合物均对棉蚜显示出80%以上的杀虫率。
(试验例10)对黄曲条跳甲的效力试验
以使本发明化合物成为31ppm的方式将乳剂(I)用水稀释,制备试验用药液。向种植于3寸钵的青梗菜苗(第7片叶展开期)散布前述试验用药液。使青梗菜苗风干,接着,放入塑料杯中。向其中投放10只黄曲条跳甲(Phyllotreta striolata)成虫。在温度25℃、湿度65%的恒温室内保存,在从放虫起7天后进行生死判定,算出杀虫率。试验反复进行2次。
针对化合物编号d-1、d-2、d-4、d-9、d-10、d-12、d-13、d-15、d-18、d-20、d-22、d-23、d-25、d-26、d-27、d-29、d-33、d-34及e-2的化合物,进行对黄曲条跳甲成虫的效力试验。任一化合物均对黄曲条跳甲成虫显示80%以上的杀虫率。
从本发明的(杂)芳基咪唑化合物中随机选择的化合物均发挥如上所述的效果,因此可理解为本发明的(杂)芳基咪唑化合物包括未尽数例示的化合物,为具有防除有害生物、尤其是杀螨、杀虫等效果的化合物。另外,可理解为对于体外寄生虫等对人畜有害的寄生虫也具有效果的化合物。
Claims (11)
1.式(II)所示的化合物、其立体异构体、互变异构体或它们的盐,
式(II)中,
X为可以被氰基或C1-6烷基取代的C3~8环烷基,
R1为C1~6烷基硫基、或者C1~6烷基磺酰基,
R2为C1~6烷基,
R3为氢原子或卤代基;
R4为C1~4卤代烷基;
碳-碳立体双键表示E体或Z体或者它们的混合物。
2.式(III)~式(X)中的任一者所示的化合物、其立体异构体、互变异构体或它们的盐,
式(IV)中的碳-碳立体双键表示E体或Z体或者它们的混合物,
式(VII)中的碳-碳立体双键表示E体或Z体或者它们的混合物,
3.有害生物防除剂,其含有选自由权利要求1或2所述的化合物、其立体异构体、互变异构体及它们的盐组成的组中的至少1者作为有效成分。
4.杀虫或杀螨剂,其含有选自由权利要求1或2所述的化合物、其立体异构体、互变异构体及它们的盐组成的组中的至少1者作为有效成分。
5.体外寄生虫防除剂,其含有选自由权利要求1或2所述的化合物、其立体异构体、互变异构体及它们的盐组成的组中的至少1者作为有效成分。
6.体内寄生虫防除剂或驱除剂,其含有选自由权利要求1或2所述的化合物、其立体异构体、互变异构体及它们的盐组成的组中的至少1者作为有效成分。
7.种子处理剂或营养繁殖器官处理剂,其含有选自由权利要求1或2所述的化合物、其立体异构体、互变异构体及它们的盐组成的组中的至少1者作为有效成分。
8.水稻育苗箱处理用农药粒状组合剂,其含有选自由权利要求1或2所述的化合物、其立体异构体、互变异构体及它们的盐组成的组中的至少1者作为有效成分。
9.土壤处理剂,其含有选自由权利要求1或2所述的化合物、其立体异构体、互变异构体及它们的盐组成的组中的至少1者作为有效成分。
10.饵剂,其含有选自由权利要求1或2所述的化合物、其立体异构体、互变异构体及它们的盐组成的组中的至少1者作为有效成分。
11.植物生长促进剂,其含有选自由权利要求1或2所述的化合物、其立体异构体、互变异构体及它们的盐组成的组中的至少1者作为有效成分。
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CA3115968A1 (en) | 2020-05-07 |
MA54184A (fr) | 2022-02-09 |
WO2020090585A1 (ja) | 2020-05-07 |
KR20210084457A (ko) | 2021-07-07 |
EP3878842A1 (en) | 2021-09-15 |
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US20210380554A1 (en) | 2021-12-09 |
IL282553B1 (en) | 2024-02-01 |
BR112021006860A2 (pt) | 2021-08-10 |
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AU2019371591B2 (en) | 2024-05-02 |
PE20211502A1 (es) | 2021-08-11 |
JP7296397B2 (ja) | 2023-06-22 |
AU2019371591A1 (en) | 2021-04-15 |
TWI742454B (zh) | 2021-10-11 |
CL2021001079A1 (es) | 2021-10-01 |
JPWO2020090585A1 (ja) | 2021-10-14 |
TW202024054A (zh) | 2020-07-01 |
IL282553A (en) | 2021-06-30 |
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