CN102378754B - 3-氨基乙二酰基氨基苯甲酰胺衍生物及以其作为有效成分的杀虫、杀螨剂 - Google Patents
3-氨基乙二酰基氨基苯甲酰胺衍生物及以其作为有效成分的杀虫、杀螨剂 Download PDFInfo
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- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
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- General Health & Medical Sciences (AREA)
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- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明提供用于杀虫、杀螨剂的3-氨基乙二酰基氨基苯甲酰胺衍生物。该3-氨基乙二酰基氨基苯甲酰胺衍生物如下式所示。(式[1]中,R1和R2例如表示C1~C3烷氧基、C1~C3卤代烷氧基,R3和R4例如表示C1~C8烷基、C1~C8卤代烷基,R5表示C1~C5卤代烷基,R6和R7例如表示氢原子、C1~C5烷基,Y例如表示氢原子、卤原子,Z例如表示氢原子等。n表示0~4的整数,m表示0~2的整数)。
Description
技术领域
本发明涉及新的3-氨基乙二酰基氨基苯甲酰胺衍生物以及含有其作为有效成分的杀虫、杀螨剂。
背景技术
公知3-酰基氨基苯甲酰胺类等作为杀虫剂是有用的(例如专利文献1~24)。
进一步地,还公知以下的化合物A、B所示的3-酰基氨基苯甲酰胺类作为杀虫剂是有用的(例如专利文献25)。
但是,专利文献25中公开的化合物为3-酰基氨基部分具有烷氧基乙二酰基氨基结构的化合物,对于具有氨基乙二酰基氨基结构的化合物没有特别公开。
现有技术文献
专利文献
专利文献1:WO2005-021488号公报
专利文献2:WO2005-073165号公报
专利文献3:WO2006-137376号公报
专利文献4:WO2006-137395号公报
专利文献5:日本特开2006-225340号公报
专利文献6:WO2007-013150号公报
专利文献7:WO2007-013332号公报
专利文献8:WO2007-017075号公报
专利文献9:日本特开2007-099761号公报
专利文献10:WO2007-128410号公报
专利文献11:日本特开2007-119416号公报
专利文献12:日本特开2007-302617号公报
专利文献13:WO2008-000438号公报
专利文献14:WO2008-012027号公报
专利文献15:WO2008-074427号公报
专利文献16:WO2008-075453号公报
专利文献17:WO2008-075454号公报
专利文献18:WO2008-075459号公报
专利文献19:WO2008-075465号公报
专利文献20:WO2008-107091号公报
专利文献21:WO2009-049844号公报
专利文献22:WO2009-049845号公报
专利文献23:WO2009-080203号公报
专利文献24:日本特开2009-209090号公报
专利文献25:日本特开2006-306771号公报。
发明内容
本发明的目的在于,提供对各种害虫和螨表现出高的效果、具有氨基乙二酰基氨基结构的化合物。
本发明人为了解决上述课题进行了深入研究,结果发现,下式所示的具有氨基乙二酰基氨基结构的化合物为具有上述特征的有用的化合物,从而完成了本发明。
即,本发明涉及下式[1]表示的3-氨基乙二酰基氨基苯甲酰胺衍生物(以下简称为“本发明的化合物”),以及含有该衍生物作为有效成分的杀虫、杀螨剂(以下简称为“本发明的杀虫、杀螨剂”)。
(式中,R1和R2分别独立地表示氢原子、C1~C3烷氧基、C1~C3卤代烷氧基、卤原子、C1~C5烷基。
R3和R4分别独立地表示氢原子、C1~C8烷基、C1~C8卤代烷基、烯丙基、C3~C8环烷基、C3~C6环烷基C1~C4烷基。其中,R3和R4可以相互键合形成C3~C6亚烷基键,R5表示C1~C5卤代烷基,
R6和R7分别独立地表示氢原子、C1~C5烷基、C3~C8环烷基、C1~C5卤代烷基、C1~C3烷氧基C1~C4烷基、C2~C6烯基、C2~C6卤代烯基、C1~C4烷基羰基、C1~C4卤代烷基羰基、C1~C4烷基磺酰基、C1~C4卤代烷基磺酰基、C1~C3烷氧基羰基或C1~C3卤代烷氧基羰基,
Y分别独立地表示氢原子、卤原子、羟基、硝基、氰基、C1~C5烷基、C1~C5卤代烷基、C1~C3烷基氨基、二C1~C3烷基氨基、C1~C3烷氧基或C1~C3卤代烷氧基,
Z分别独立地表示氢原子、卤原子、羟基、硝基、氰基、C1~C5烷基、C1~C5卤代烷基、C1~C3烷氧基或C1~C3卤代烷氧基,
n表示0~4的整数,m表示0~2的整数。)
本发明的化合物对害虫和螨表现出优异的效果。
具体实施方式
以下对本发明进行具体的说明。
式[1]中,R1和R2分别独立地表示氢原子、C1~C3烷氧基、C1~C3卤代烷氧基、卤原子或C1~C5烷基。
其中,C1~C3烷氧基可以具有支链,C1~C3烷氧基可以优选举出例如甲氧基、乙氧基、异丙氧基等。C1~C3卤代烷氧基可以具有支链,作为C1~C3卤代烷氧基,可以优选举出例如三氟甲氧基、2,2,2-三氟乙氧基等。作为卤原子,可以优选举出例如氟原子、氯原子、溴原子、碘原子。作为C1~C5烷基,为直链状或可以具有支链的烷基,可以优选举出例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、2-戊基、3-戊基、新戊基、叔戊基等。特别是作为R1,优选为甲基、乙基、异丙基、甲氧基、三氟甲氧基。作为R2,优选为氢原子、甲基、乙基、氯原子、溴原子、碘原子。
R3和R4分别独立地表示氢原子、C1~C8烷基、C1~C8的卤代烷基、烯丙基、C3~C8环烷基或C3~C6环烷基C1~C4烷基。
其中,作为C1~C8烷基,为直链状或可以具有支链的烷基,可以优选举出例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、2-戊基、3-戊基、新戊基、叔戊基、正己基、叔辛基、正辛基等。作为C1~C8烷基,优选为C1~C6烷基。
作为C1~C6烷基,为直链状或可以具有支链的烷基,可以优选举出例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、2-戊基、3-戊基、新戊基、叔戊基、正己基等。
C1~C8卤代烷基为直链状或可以具有支链的卤代烷基,可以优选举出例如单氟甲基、二氟甲基、三氟甲基、单氯甲基、二氯甲基、三氯甲基、单溴甲基、二溴甲基、三溴甲基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2,2-二氟乙基、1-氯乙基、2-氯乙基、2,2-二氯乙基、2,2,2-三氯乙基、1-溴乙基、2-溴乙基、2,2-二溴乙基、2,2,2-三溴乙基、2-碘乙基、五氟乙基、2-氯-1,1,2,2-四氟乙基、2-溴-1,1,2,2-四氟乙基、2-碘-1,1,2,2-四氟乙基、3-氟丙基、3-氯丙基、3-溴丙基、1,3-二氟-2-丙基、3,3-二氟丙基、3,3,3-三氟丙基,
3,3,3-三氯丙基、1,3-二氯-2-丙基、1,1,1-三氟-2-丙基、1-氯-3-氟-2-丙基、1,1,1,3,3,3-六氟-2-丙基、1,1,1,3,3,3-六氟-2-氯-2-丙基、2-溴-1,1,1,3,3,3-六氟-2-丙基、2,2,3,3,3-五氟丙基、七氟异丙基、七氟正丙基、1-氯-1,1,2,3,3,3-六氟-2-丙基、1-溴-1,1,2,3,3,3-六氟-2-丙基、2-氯-1,1,2,3,3,3-六氟正丙基、2-溴-1,1,2,3,3,3-六氟正丙基、4-氟丁基、4,4,4-三氟丁基、九氟正丁基、九氟-2-丁基、4,4,5,5,5-五氟戊基、3,3,4,4,5,5,5-七氟戊基、十一氟-2-戊基、十一氟-3-戊基、十一氟正戊基、6,6,6-三氟己基、1H,1H-十五氟辛基等。作为C1~C8卤代烷基,优选举出C1~C6卤代烷基。
C1~C6卤代烷基为直链状或可以具有支链的卤代烷基,可以优选举出例如单氟甲基、二氟甲基、三氟甲基、单氯甲基、二氯甲基、三氯甲基、单溴甲基、二溴甲基、三溴甲基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2,2-二氟乙基、1-氯乙基、2-氯乙基、2,2-二氯乙基、2,2,2-三氯乙基、1-溴乙基、2-溴乙基、2,2-二溴乙基、2,2,2-三溴乙基、2-碘乙基、五氟乙基、2-氯-1,1,2,2-四氟乙基、2-溴-1,1,2,2-四氟乙基、2-碘-1,1,2,2-四氟乙基、3-氟丙基、3-氯丙基、3-溴丙基、1,3-二氟-2-丙基、3,3-二氟丙基、3,3,3-三氟丙基,
3,3,3-三氯丙基、1,3-二氯-2-丙基、1,1,1-三氟-2-丙基、1-氯-3-氟-2-丙基、1,1,1,3,3,3-六氟-2-丙基、1,1,1,3,3,3-六氟-2-氯-2-丙基、2-溴-1,1,1,3,3,3-六氟-2-丙基、2,2,3,3,3-五氟丙基、七氟异丙基、七氟正丙基、1-氯-1,1,2,3,3,3-六氟-2-丙基、1-溴-1,1,2,3,3,3-六氟-2-丙基、2-氯-1,1,2,3,3,3-六氟正丙基、2-溴-1,1,2,3,3,3-六氟正丙基、4-氟丁基、4,4,4-三氟丁基、九氟正丁基、九氟-2-丁基、4,4,5,5,5-五氟戊基、3,3,4,4,5,5,5-七氟戊基、十一氟-2-戊基、十一氟-3-戊基、十一氟正戊基、6,6,6-三氟己基等。
作为C3~C8环烷基,可以具有支链,可以优选举出例如环丙基、1-甲基环丙基、2-甲基环丙基、环丁基、环戊基、环己基等。作为C3~C8环烷基,可以优选举出C3~C6环烷基。
作为C3~C6环烷基C1~C4烷基,可以具有支链,可以优选举出例如环丙基甲基、1-环丙基乙基、环丁基甲基等。
R3和R4可以相互键合形成C3~C8亚烷基键,作为C3~C8亚烷基键,可以优选举出例如(CH2)3、(CH2)4、(CH2)5、(CH2)6等。作为C3~C8亚烷基键,可以优选举出C3~C6亚烷基键。
特别是作为R3,优选为甲基、乙基。作为R4,优选为甲基、乙基、正丙基、异丙基、环丙基、叔丁基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基。
R5表示C1~C5卤代烷基。
其中,C1~C5卤代烷基为直链状或可以具有支链的卤代烷基,可以优选举出例如单氟甲基、二氟甲基、三氟甲基、单氯甲基、二氯甲基、三氯甲基、单溴甲基、二溴甲基、三溴甲基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2,2-二氟乙基、1-氯乙基、2-氯乙基、2,2-二氯乙基、2,2,2-三氯乙基、1-溴乙基、2-溴乙基、2,2-二溴乙基、2,2,2-三溴乙基、2-碘乙基、五氟乙基、2-氯-1,1,2,2-四氟乙基、2-溴-1,1,2,2-四氟乙基、2-碘-1,1,2,2-四氟乙基、3-氟丙基、3-氯丙基、3-溴丙基、1,3-二氟-2-丙基、3,3-二氟丙基、3,3,3-三氟丙基、3,3,3-三氯丙基、1,3-二氯-2-丙基、1,1,1-三氟-2-丙基、1-氯-3-氟-2-丙基、1,1,1,3,3,3-六氟-2-丙基、1,1,1,3,3,3-六氟-2-氯-2-丙基,
2-溴-1,1,1,3,3,3-六氟-2-丙基、2,2,3,3,3-五氟丙基、七氟异丙基、七氟正丙基、1-氯-1,1,2,3,3,3-六氟-2-丙基、1-溴-1,1,2,3,3,3-六氟-2-丙基、2-氯-1,1,2,3,3,3-六氟正丙基、2-溴-1,1,2,3,3,3-六氟正丙基、4-氟丁基、4,4,4-三氟丁基、九氟正丁基、九氟-2-丁基、4,4,5,5,5-五氟戊基、3,3,4,4,5,5,5-七氟戊基、十一氟-2-戊基、十一氟-3-戊基、十一氟正戊基等。
R6和R7分别独立地表示氢原子、C1~C5烷基、C3~C8环烷基、C1~C5卤代烷基、C1~C3烷氧基C1~C4烷基、C2~C6烯基、C2~C6卤代烯基、C1~C4烷基羰基、C1~C4卤代烷基羰基、C1~C4烷基磺酰基、C1~C4卤代烷基磺酰基、C1~C3烷氧基羰基或C1~C3卤代烷氧基羰基。
其中,C1~C5烷基、C3~C8环烷基和C1~C5卤代烷基与上述说明的C1~C5烷基、C3~C8环烷基和C1~C5卤代烷基相同。
作为C1~C3烷氧基C1~C4烷基,为直链状或可以具有支链的烷氧基烷基,可以优选举出例如甲氧基甲基、乙氧基甲基、2-甲氧基乙基等。
作为C2~C6烯基,为直链状或可以具有支链的烯基,可以优选举出例如乙烯基、烯丙基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、2-丁烯基、3-丁烯基等。
作为C2~C6卤代烯基,为直链状或可以具有支链的卤代烯基,可以优选举出例如2-氯-2-丙烯基、3-氯-2-丙烯基、2-溴-2-丙烯基、3-溴-2-丙烯基、3,3-二氟-2-丙烯基、3,3-二氯-2-丙烯基、3,3-二溴-2-丙烯基、2,3-二溴-2-丙烯基、4,4-二氟-3-丁烯基、3,4,4-三溴-3-丁烯基等。
作为C1~C4烷基羰基,为直链状、环状或可以具有支链的烷基羰基,可以优选举出例如乙酰基、丙酰基、异丙基羰基、环丙基羰基等。
作为C1~C4卤代烷基羰基,为直链状或可以具有支链的卤代烷基羰基,可以优选举出例如三氟乙酰基、五氟丙酰基、三氯乙酰基、氯乙酰基、溴乙酰基、3-氯丙酰基等。
作为C1~C4烷基磺酰基,为直链状、环状或可以具有支链的烷基磺酰基,可以优选举出例如甲基磺酰基、乙基磺酰基、正丙基磺酰基、异丙基磺酰基、环丙基磺酰基、正丁基磺酰基、异丁基磺酰基、仲丁基磺酰基、叔丁基磺酰基等。
作为C1~C4卤代烷基磺酰基,为直链状或可以具有支链的卤代烷基磺酰基,可以优选举出例如三氟甲基磺酰基、五氟乙基磺酰基、2,2,2-三氟乙基磺酰基、七氟正丙基磺酰基、七氟异丙基磺酰基、九氟正丁基磺酰基、九氟仲丁基磺酰基等。
作为C1~C3烷氧基羰基,为直链状或可以具有支链的烷氧基羰基,可以优选举出例如甲氧基羰基、乙氧基羰基、异丙氧基羰基等。
作为C1~C3卤代烷氧基羰基,为直链状或可以具有支链的卤代烷氧基羰基,可以优选举出例如氯甲氧基羰基、2,2,2-三氟乙氧基羰基、3,3,3-三氟丙氧基羰基、3,3,3-三氯丙氧基羰基等。
特别是作为R6,优选为氢原子、甲基。作为R7,优选为氢原子、甲基。
Y分别独立地表示氢原子、卤原子、羟基、硝基、氰基、C1~C5烷基(优选为C1~C3烷基)、C1~C5卤代烷基(优选为C1~C3卤代烷基)、C1~C3烷基氨基、二C1~C3烷基氨基、C1~C3烷氧基或C1~C3卤代烷氧基。
其中,作为C1~C3烷基,为直链状或可以具有支链的烷基,可以优选举出例如甲基、乙基、正丙基、异丙基等。
作为C1~C3卤代烷基,为直链状或可以具有支链的卤代烷基,可以优选举出例如二氟甲基、三氟甲基、五氟乙基等。
作为C1~C3烷基氨基,为直链状、环状或可以具有支链的烷基氨基,可以优选举出例如甲基氨基、乙基氨基、正丙基氨基、异丙基氨基、环丙基氨基等。
作为二C1~C3烷基氨基,为直链状、环状或可以具有支链的二烷基氨基,可以优选举出例如二甲基氨基、甲基乙基氨基、二乙基氨基、二正丙基氨基、二异丙基氨基等。
其它基团的定义如上述定义所述。
特别是作为Y,优选为氢原子、卤原子。
Z分别独立地表示氢原子、卤原子、羟基、硝基、氰基、C1~C5烷基(优选为C1~C3烷基)、C1~C5卤代烷基、C1~C3烷氧基或C1~C3卤代烷氧基。
其它基团的定义如上述所定义。
特别是作为Z,优选为氢原子。
n表示0~4的整数。
m表示0~2的整数。
本发明的化合物中,根据取代基的种类有时存在构象异构体,本发明包含以任意的比率含有构象异构体的混合物。此外,本发明的化合物中,有时存在起因于不对称碳原子的光学异构体,本发明包含全部以任意的比率含有光学活性体的混合物。
本发明的化合物为新化合物,例如可以按照下述合成方案1~3来制备。
方案1
(式中,R1、R2、R3、R4、R5、R6、R7、n、m、Y和Z如式[1]中所定义,R8表示低级烷基。低级烷基例如为碳原子数为1~5左右的烷基。)
(1) 通式[4]的化合物的制备
化合物[4]通过使化合物[2]与化合物[3]反应来得到。该反应可以在溶剂和碱的存在下、或非存在下进行。
作为溶剂,若为不直接参与本反应的溶剂则不特别限定,可以举出例如苯、甲苯、二甲苯等芳烃类,丙酮、甲乙酮、甲基异丁基酮等酮类,氯仿、二氯甲烷等卤代烃类,乙酸甲酯、乙酸乙酯等酯类,四氢呋喃、二烷、二乙醚、1,2-二甲氧基乙烷等醚类,水,乙腈、N,N-二甲基甲酰胺、N-甲基吡咯烷酮、二甲基亚砜等极性溶剂类或上述溶剂的混合溶剂。
作为碱,可以举出三乙胺、吡啶、1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)、4-二甲基氨基吡啶等有机碱,氢氧化钠、氢氧化钾等碱金属氢氧化物,氢氧化钙等碱土类金属氢氧化物,碳酸钠、碳酸钾等碱金属碳酸盐,碳酸钙等碱土类金属碳酸盐,碳酸氢钠等碱金属碳酸氢盐,甲醇钠、乙醇钾等金属醇盐。反应温度例如为-30℃~150℃,优选为-5℃~80℃。反应结束后,目的物可以通过常规方法从反应体系分离,根据需要通过利用溶剂进行的洗涤、重结晶、柱色谱等纯化,可以制备目的物。此外,还可以不从反应体系分离目的物来用于以下的步骤中。
化合物[2]为公知的化合物。作为本反应的原料化合物的通式[3]表示的苯胺衍生物,可以按照WO2005-021488号公报或WO2005-073165号公报中公开的制备方法来制备。
(2) 通式[1]的化合物的制备
通过使上述化合物[4]与化合物[5]反应,得到化合物[1]。该反应可以在溶剂和碱的存在下、或非存在下进行。
作为溶剂,若为不直接参与本反应的溶剂则不特别限定,可以举出例如苯、甲苯、二甲苯等芳烃类,丙酮、甲乙酮、甲基异丁基酮等酮类,氯仿、二氯甲烷等卤代烃类,乙酸甲酯、乙酸乙酯等酯类,四氢呋喃、二烷、二乙醚、1,2-二甲氧基乙烷等醚类,水,乙腈、N,N-二甲基甲酰胺、N-甲基吡咯烷酮、二甲基亚砜等极性溶剂类,甲醇、乙醇、异丙醇等醇类或上述溶剂的混合溶剂。
作为碱,可以举出三乙胺、吡啶、1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)、4-二甲基氨基吡啶等有机碱,氢氧化钠、氢氧化钾等碱金属氢氧化物,氢氧化钙等碱土类金属氢氧化物,碳酸钠、碳酸钾等碱金属碳酸盐,碳酸钙等碱土类金属碳酸盐,碳酸氢钠等碱金属碳酸氢盐,甲醇钠、乙醇钾等金属醇盐。反应温度例如为-30℃~150℃,优选为-5℃~80℃。反应结束后,目的物可以通过常规方法从反应体系分离,根据需要通过利用溶剂进行的洗涤、重结晶、柱色谱等纯化,可以制备目的物。
方案2
(式中,R1、R2、R3、R4、R5、R6、R7、n、m、Y和Z如式[1]中所定义。)
方案2的反应可以在缩合剂的存在下,溶剂及碱的存在下、或非存在下进行。作为溶剂,可以举出例如苯、甲苯、二甲苯等芳烃类,丙酮、甲乙酮、甲基异丁基酮等酮类,氯仿、二氯甲烷等卤代烃类,水,乙酸甲酯、乙酸乙酯等酯类,或四氢呋喃、二烷、二乙醚、1,2-二甲氧基乙烷等醚类,水,乙腈、N,N-二甲基甲酰胺、N-甲基吡咯烷酮、二甲基亚砜等极性溶剂类,甲醇、乙醇、异丙醇等醇类或上述溶剂的混合溶剂。
作为碱,可以举出三乙胺、吡啶、1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)、4-二甲基氨基吡啶等有机碱,氢氧化钠、氢氧化钾等碱金属氢氧化物,氢氧化钙等碱土类金属氢氧化物,碳酸钠、碳酸钾等碱金属碳酸盐,碳酸钙等碱土类金属碳酸盐,碳酸氢钠等碱金属碳酸氢盐,甲醇钠、乙醇钾等金属醇盐。
作为反应中使用的缩合剂,可以举出例如1,3-二环己基碳二亚胺(DCC)、2-氯-1-甲基吡啶碘化物、羰基二咪唑(CDI)、三氟乙酸酐等。反应温度例如为-30℃~150℃,优选为-5℃~80℃。反应结束后,目的物可以通过常规方法从反应体系分离,根据需要通过利用溶剂进行的洗涤、重结晶、柱色谱等纯化,可以制备目的物。
方案3
(式中,R1、R2、R3、R4、R5、R6、R7、n、m、Y和Z如式[1]中所定义,X表示卤原子)
方案3的反应可以在溶剂及碱的存在下、或非存在下进行。
作为溶剂,若为不直接参与本反应的溶剂则不特别限定,可以举出例如苯、甲苯、二甲苯等芳烃类,丙酮、甲乙酮、甲基异丁基酮等酮类,氯仿、二氯甲烷等卤代烃类,乙酸甲酯、乙酸乙酯等酯类,四氢呋喃、二烷、二乙醚、1,2-二甲氧基乙烷等醚类,水,乙腈、N,N-二甲基甲酰胺、N-甲基吡咯烷酮、二甲基亚砜等极性溶剂类或上述溶剂的混合溶剂。
作为碱,可以举出三乙胺、吡啶、1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)、4-二甲基氨基吡啶等有机碱,氢氧化钠、氢氧化钾等碱金属氢氧化物,氢氧化钙等碱土类金属氢氧化物,碳酸钠、碳酸钾等碱金属碳酸盐,碳酸钙等碱土类金属碳酸盐,碳酸氢钠等碱金属碳酸氢盐,甲醇钠、乙醇钾等金属醇盐。反应温度例如为-30℃~150℃,优选为-5℃~80℃。反应结束后,目的物可以通过常规方法从反应体系分离,根据需要通过利用溶剂进行的洗涤、重结晶、柱色谱等纯化,可以制备目的物。
含有式[1]所示的本发明的化合物作为有效成分的本发明的杀虫、杀螨剂,在农业、室内、森林、家畜、卫生等场所下,可以用于预防、驱除带来灾害的生物的。以下示出具体的使用场所、对象有害生物、使用方法,但是本发明的内容不被它们所限定。
本发明的化合物可以用于对农作物,例如食用作物(稻、大麦、小麦、黑麦、燕麦等麦类,玉米、马铃薯、甘薯、芋头、大豆、小豆、蚕豆、豌豆、菜豆、花生等豆类等)、蔬菜(圆白菜、白菜、萝卜、芜菁、花椰菜、菜花、油菜等十字花科作物,南瓜、黄瓜、西瓜、甜瓜、香瓜等瓜类,茄子、西红柿、青椒、胡椒、秋葵、菠菜、莴苣、藕、胡萝卜、牛蒡、蒜、洋葱、葱等葱类等)、果树·果实类(苹果、柑桔类、梨、葡萄、桃、梅、樱桃、胡桃、栗、杏仁、香蕉、草莓等)、香料等鉴赏作物(薰衣草、迷迭香、百里香、荷兰芹、胡椒、生姜等)、经济作物(烟、茶、甜菜、甘蔗、蛇麻草、棉、麻、橄榄、橡胶、咖啡等)、牧草·饲料用作物(梯牧草、三叶草、苜蓿、玉米、高粱类、鸭茅、禾本科牧草、豆科牧草等)、草皮类(朝鲜草皮、糠穗草等)、林木(冷杉类、虾夷松类、松类、罗汉柏、杉、扁柏等)或观赏植物(菊、蔷薇、康乃馨、兰等草本·花卉类,银杏、樱花类、珊瑚木等庭木等)带来损害的节肢动物类、软体动物类、线虫类等有害生物的防除。
作为具体的有害生物,为节肢动物门昆虫纲的鳞翅目(Lepidoptera),例如夜蛾科的棉铃虫(Helicoverpa armigera)、夜蛾属(Heliothis spp.)、黄地老虎(Agrotis segetum)、显银纹夜蛾(Autographa nigrisigna) 、粉纹夜蛾(Trichoplusia ni)、甘蓝菜蛾(Mamestra brassicae)、甜菜夜蛾(Spodoptera exigua)、斜纹夜蛾(Spodoptera litura)等,巢蛾科的小菜蛾(Plutella xylostella)等,卷蛾科的小黄卷叶蛾(Adoxophyes orana fasciata)、茶小卷叶蛾(Adoxophyes honmai)、杏黄卷蛾(Archips fuscocupreanus)、茶长卷叶蛾(Homona magnanima)、茶细蛾(Caloptilia theivora)、梨小食心虫(Grapholita molesta)等,蓑蛾科的茶大蓑蛾(Eumeta minuscule)等,潜蛾科的银纹潜叶蛾(Lyonetia prunifoliella malinella)、桃潜叶蛾(Lyonetia clerkella)等,叶潜蛾科的柑桔潜叶蛾(Phyllocnistis citrella) 等、细蛾科的金纹小潜细蛾(Phyllonorycter ringoniella)等,
伪菜蛾科的葱菜蛾(Acrolepiopsis sapporensis)等,透翅蛾科的栎小透翅蛾(Synanthedon quercus)等,展足蛾科的柿蒂虫(Stathmopoda masinissa)等,麦蛾科的棉红铃虫(Pectinophora gossypiella)等,蛀果蛾科的桃小食心虫(Carposina niponensis)等,刺蛾科的黄刺蛾(Monema flavecens)、丽绿刺蛾(Parasa lepida)、背刺蛾(Scopelodes contracus)等,草螟科的二化螟(Chilo suppressalis)、三化螟(Scirpophaga incertulas)、稻纵卷叶螟(Cnaphalocrocis medinalis)、菜螟(Hellulla undalis)、桃蛀螟(Conogethes punctiferlis)、瓜绢野螟(Diaphania indica)、草地毛虫(Parapediasia teterrella)等,弄蝶科的稻弄蝶(Parnara guttata)等,凤蝶科的柑桔凤蝶(Papilio xuthus)等,粉蝶科的纹白蝶(Pieris rapae crucivora)等,灰蝶科的亮灰蝶(Lampides boeticus)等,尺蛾科的大造桥虫(Ascotis selenaria)等,天蛾科的甘薯天蛾(Agrius convolvuli)等,舟蛾科的苹掌舟蛾(Phalera flavescens)等,毒蛾科的茶毛虫(Euproctis pseudoconspersa)、旋古毒蛾(Orygia recens approximans)等,灯蛾科的黄领麻纹灯蛾(Spilosoma imparilis)、美国白蛾(Hyphantria cunea)等,女贞细卷蛾(Endopiza viteana)、苹果蠹蛾(Laspeyresia pomonella)等的成虫、幼虫及卵;
鞘翅目(Coleoptera),例如金龟子科的大绿丽金龟(Anomala cuprea)、日本豆金龟(Popillia japonica)、小青花金龟(Oxycetonia jucunda)、黄绿丽金龟(Anomala geniculata)等,吉丁科的柑桔窄吉丁(Agrilus auriventris)等,叩头虫科的红薯梳爪叩甲(Melanotus fortnumi)等,瓢虫科的茄二十八星瓢虫(Epilachna vigintioctopunctata)等,天牛科的星天牛(Anoplophora malasiaca)、葡萄虎天牛(Xylotrechus pyrrhoderus)等,叶甲科黄守瓜(Aulacophora femoralis)、玉米根虫(Diabrotica spp.)、黄曲条跳甲(Phyllotreta striolata)、甜菜大龟甲(Cassida nebulosa)、小猿叶虫(Phaedon brassicae)、水稻负泥虫(Oulema oryzae)、墨西哥豆瓢虫(Epilachna varivestis)、马铃薯甲虫(Leptinotarsa decemlineata)等,卷象科的梨虎(Rhynchites heros)等,三锥象虫科的甘薯象虫(Cylas formicarius)等,象甲科的板栗象甲(Curculio sikkimensis)、稻水象甲(Lissorhoptrus oryzophilus)、墨西哥棉铃象虫(Anthonomus gradis grandis) 、シバオサゾウムシ(Sphenophrus venatus vestitus)等,露尾甲科的ヒメヒラタケシキスイ(Epuraea domina)等的成虫、幼虫及卵;
半翅目(Hemiptera)的异翅亚目(Heteroptera),例如蝽科的皱纹菜蝽(Eurydema rugosum)、二星蝽(Eysarcoris lewisi)、白星蝽(Eysarcoris parvus)、稻绿蝽(Nezara viridula)、小珀椿象(Plautia stali)、茶翅蝽(Halymorpha mista)等,异蝽科的梨蝽象(Urochela luteovoria)等,长蝽科的コバネヒョウタンナガカメムシ(Togo hemipterus)等,缘蝽科的点蜂缘椿象(Riptortus clavatus)、稻棘缘椿(Cletus punctiger)等,蛛缘蝽科的中华稻缘蝽(Leptocorisa chinensis)等,红蝽科的棉红椿(Dysdeercus cingulatus)等,网蝽科的梨网蝽(Stephanitis nashi)、杜鹃网蝽(Stephanitis pyrioides)等,盲蝽科的后丽盲蝽(Apolygus spinolai)、赤条纤盲蝽(Stenotus rubrovittalus)、条赤须盲蝽(Trigonotylus coelestialium)等,龟蝽科的臭蝽(Megacopta punctatissimum)等的成虫、幼虫及卵;
半翅目(Hemiptera)的同翅亚目(Homoptera),例如蝉科的蟪蛄(Platypleura kaempferi)等,叶蝉科的葡萄阿小叶蝉(Arboridia apicalis)、大贯小绿叶蝉(Empoasca onukii)、黑尾叶蝉(Nephotettix cincticeps)、二点黑尾叶蝉(Nephotettix virescens)等,飞虱科的灰飞虱(Laodelphax striatellus)、褐飞虱(Nilaparvata lugens)、白背飞虱(Sogatella furcifera)等,蛾蜡蝉科的碧蛾蜡蝉(Geisha distinctissima)等,木虱科的梨木虱(Psylla pyrisuga)、柑桔木虱(Diaphorina citri)等,粉虱科的黑刺粉虱(Aleurocanthus spiniferus)、银叶粉虱(Bemisia argentifolii)、烟粉虱(Bemisia tabaci)的各种生物型、柑桔粉虱(Dialeurodes citri)、温室白粉虱(Trialeurodes vaporariorum)等,
根瘤蚜科的葡萄根瘤蚜(Viteus vitifolii)等,蚜科的绣线菊蚜(Aphis citricola)、豆蚜(Aphis craccivora)、棉蚜(Aphis gossypii)、茄沟无网蚜(Aulacorthum solani)、甘蓝蚜(Brevicoryne brassicae)、茶蚜(Toxoptera aurantii)、桔蚜(Toxoptera citricidus)、木兰沟无网蚜(Aulacorthum magnoliae)、梨二叉蚜(Schizaphis piricola)、梨绿蚜(Nippolachnus piri)、萝卜蚜(Lipaphis erysimi)、桃大尾蚜(Hyalopterus pruni)、キククギケアブラムシ(Pleotrichophorus chrysanthemi)、菊小长管蚜(Macrosiphoniella sanborni)、豌豆修尾蚜(Megoura crassicauda)、玫瑰蚜(Sitobion ibarae)、马铃薯长管蚜(Macrosiphum euphorbiae)、桃纵卷叶蚜(Myzus varians)、桃蚜(Myzus persicae)、红腹缢管蚜(Rhopalosiphum rufiabdominalis)、禾谷缢管蚜(Rhopalosiphum padi)、麦长管蚜(Sitobion akebiae)、苹果绵蚜(Eriosoma lanigerum)等,绵蚧科的吹绵蚧(Icerya purchasi)等,粉蚧科的康氏粉蚧(Pseudococcus comstocki)、ミカンコナカイガラムシ(Phenacoccus viburnae)、フジコナカイガラム(Phenacoccus kraunhiae)等,蚧科的角蜡蚧(Ceroplastes ceriferus)、红蜡蚧(Ceroplastes rubens)等,盾蚧科的红圆蚧(Aonidiella aurantii)、梨圆蚧(Comstockaspis perniciosa)、桑白蚧(Pseudaulacaspis pentagoa) 、矢尖盾蚧(Unaspis yanonensis)等的成虫、幼虫及卵;
缨翅目(Thysanoptera),例如蓟马科的茶黄蓟马(Scirtothrips dorsalis)、棕榈蓟马(Thrips palmi)、烟蓟马(Thrips tabaci) 、粗毛蓟马(Thrips setosus)、花蓟马(Frankliniella intonsa)、西花蓟马(Frankliniella occidentalis)、温室蓟马(Heliothrips haemorrhoidalis)等,管蓟马科的カキクダアザミウマ(Ponticulothrips diospyrosi)、稻管蓟马(Haplothrips aculeatus)等的成虫、幼虫及卵;
膜翅目(Hymenoptera),例如叶蜂科的芜菁叶蜂(Athalia rosae ruficornis)、月季叶蜂(Arge pagana)等,三节叶蜂科的苹果三节叶蜂(Arge mali)等,瘿蜂科的板栗瘿蜂(Dryocsmus kuriphilus)等,切叶峰科的月季切叶峰(Megachile nipponica nipponica)等,蚁科的日本褐蚁(Formica japonica)等的成虫、幼虫及卵;
双翅目(Diptera),例如瘿蚊科的ダイズサヤタマバエ(Asphondylia yushimai)等,实蝇科的日本樱桃实蝇(Rhacochlaena japonica)、瓜实蝇(Bactrocera cucurbitae)等,水蝇科的稻小毛眼水蝇(Hydrellia griseola)等,果蝇科的樱桃果蝇(Drosophila suzukii)等,潜蝇科的三叶斑潜蝇(Liriomyza trifolii)、豌豆彩潜蝇(Chromatomyia horticola)、稻潜蝇(Agromyza oryzae)、瓜斑潜蝇(Liriomyza bryoniae)等,花蝇科的种蝇(Delia platura)、葱蝇(Delia antiqua)等的成虫、幼虫及卵;
直翅目(Orthoptera),例如螽斯科的黑胫钩额草螽(Ruspolia lineosa)等,蟋蟀科的梨片蟋(Truljalia hibinonis)等,蝼蛄科的东方蝼蛄(Gryllotalpa orientalis)等,蝗科的小翅稻蝗(Oxya yezoensis)等的成虫、幼虫及卵;
等翅目(Isoptera),例如白蚁科的黑翅土白蚁(Odontotermes formosanus)等的成虫、幼虫及卵;
革翅目(Dermaptera),例如蠼螋科的蠼螋(Labidura riparia)等的成虫、幼虫及卵;
节肢动物门缺尾纲的弹尾目(Collembola),例如圆跳虫科的绿圆跳虫(Sminthurus viridis)等,棘跳科的マツモトシロトビムシ(Onychiurus matsumotoi)等的成虫、幼虫及卵;
节肢动物门甲壳纲的等足目(Isopada),例如ダンゴムシ科的鼠妇(Armadillidium vulgare)等的成虫、幼虫及卵;
节肢动物门蛛形纲的蜱螨目(Acari),例如跗线螨科的侧多食跗线螨(Polyphagotarsonemus latus)、樱草植食螨(Phytonemus pallidus)等,走螨科的麦圆叶爪螨(Penthaleus major)等,细须螨科的葡萄短须螨(Brevipalpus lewisi)、紫红短须螨(Brevipalpus phoenicis)等,叶螨科的柑桔叶螨(Panonychus citri)、苹果全爪螨(Panonychus ulmi)、二斑叶螨(Tetranychus urticae)、神泽氏叶螨(Tetranychus kanzawai)、山楂叶螨(Tetranychus viennensis)、针叶小爪螨(Oligonychus ununguis)、桔始叶螨(Eotetranychus kankitus)、苜蓿苔螨(Bryobia praetiosa)等,瘿螨科的皮氏刺皮瘿螨(Aculops pelekassi)、ニセナシサビダニ(Eriophyes chibaensis)、曲叶螨(Aceria tulipae)、葡萄缺节瘿螨(Colomerus vitis)、佛氏刺瘿螨(Aculus fockeui)、茶叶瘿螨(Calacarus carinatus)等,螨科的腐食酪螨(Tyrophagus putrescentiae) 、罗宾根螨(Rhizoglyphus robini)等的成虫、幼虫及卵;
软体动物门腹足纲的主扭舌目(Architaenioglossa),例如球螺科的福寿螺(Pomacea canaliculata)等,肺螺目(Plumonata),例如非洲蜗牛科的非洲大蜗牛(Achatina fulica)、嗜粘液蛞蝓科的双线嗜粘液蛞蝓(Meghimatium bilineatum)、小蛞蝓科的ニワコウラナメクジ(Milax gagates)、蛞蝓科的瓦伦西亚列蛞蝓(Lehmannina valentiana)、巴蜗牛科的蜗牛(Acusta despecta sieboldiana)等,
线虫动物门胞管肾纲的垫刃目(Tylenchida),例如粒科的马铃薯茎线虫(Ditylenchus destructor)等,矮化线虫科的克莱顿矮化线虫(Tylenchorhynchus claytoni)等,短体线虫科的穿刺短体线虫(Pratylenchus penetrans)、咖啡短体线虫(Pratylenchus coffeae)等,纽带线虫科的双宫螺旋线虫(Helicotylenchus dihystera)等,异皮线虫科的马铃薯金线虫(Globodera rostochiensis)等,根结科的南方根结线虫(Meloidogyne incognita)等,环线虫科的ワセンチュウ(Criconema jaejuense)等,粒线虫科的草莓不正茎线虫(Nothotylenchus acris)等,滑刃线虫科的草莓芽线虫(Aphelecchoides fragarriae)等,
无侧尾腺口纲的矛线目,例如长针线虫科的剑线虫属(Xiphinema sp.)、毛刺线虫科的毛刺线虫属(Trichodorus sp.)等。
本发明的化合物还可以用于在包括一般房屋的建筑物的屋内活动、加害木材及作为其加工品的木制家具类、贮藏食品、衣服、书籍等,对我们的生活带来损害的害虫的防除。作为具体的有害生物,可以举出节肢动物门昆虫纲的等翅目,例如鼻白蚁科的栖北散白蚁(Reticulitermes speratus)、台湾乳白蚁(Coptotermes formosanus)等,木白蚁科的截头堆砂白蚁(Cryptotermes domesticus)的成虫、幼虫及卵;
鞘翅目,例如隐颏象亚科的玉米象(Sitophilus zeamais)、玉米象(Sitophilus zeamais)等,豆象科的绿豆象(Callosobruchus chinensis)、豌豆象(Bruchus pisorum)、蚕豆象(Bruchus rufimanus)等,拟步行虫科的赤拟谷盗(Tribolium castaneum)、杂拟谷盗(Tribolium confusum)等,锯谷盗科的锯谷盗(Oryzaephilus surinamensis)、长角扁谷盗(Cryptolestes pusillus)等,窃蠹科的烟草甲(Lasioderma serricorne)、药材甲(Stegobium paniceum)等,皮蠹科的黑毛皮蠹(Attagenus unicolor japonicus)、小圆皮蠹(Anthrenus verbasci)、白腹皮蠹(Dermestes maculatus)等,蛛甲科的拟裸蛛甲(Gibbium aequinnoctiale)等,长蠹科的竹长蠹(Dinoderus minutus)、谷蠹(Rhizopertha dominica)等,粉蠹科的褐粉蠹(Lyctus brunneus)等的成虫、幼虫及卵;
鳞翅目,例如螟蛾科的干果斑螟(Cadra cautella)、地中海斑螟(Ephestia kuehniella)、印度谷斑螟(Plodia interpunctella)等,麦蛾科的麦蛾(Sitotroga cerealella)等,谷蛾科的衣蛾(Tinea translucens)、幕衣蛾(Tineola bisselliella)等的成虫、幼虫及卵;
啮虫目,例如窃啮科的米虱(Lepinotus reticulatus)等,虱啮科的嗜卷书虱(Liposcelis bostrychophilus)等的成虫、幼虫及卵;
蜚蠊目,例如姬蜚蠊科的德国姬蠊(Blattella germanica)等,蜚蠊科的黑胸大蠊(Periplaneta fuliginosa)、日本大蠊(Periplaneta japonica)等的成虫、幼虫及卵;
缨尾目,例如衣鱼科的毛衣鱼(Ctenolepisma villosa)、西洋衣鱼(Lepisma saccharina)等的成虫、幼虫及卵;
双翅目,例如果蝇科的黑腹果蝇(Drosophila melangogaster)等,酪蝇科的酪蝇(Piophila casei)等的成虫、幼虫及卵;
节肢动物门蛛形纲的蜱螨目,例如螨科的腐食酪螨(Tyrophagus putrescentiae)、河野脂螨(Lardoglyphus konoi)等,果螨科的甜果螨(Carpoglyphus lactis)等的成虫、幼虫及卵。
本发明的化合物还可以用于加害天然林、人工林、都市绿地的树木或减弱树势的有害生物的防除。作为具体的有害生物,可以举出节肢动物门昆虫纲的鳞翅目,例如毒蛾科的杉毒蛾(Calliteara argentata)、茶毛虫(Euproctis pseudoconspersa)、ヒメシロモンドクガ(Orygia recens approximans)、东方毒蛾(Euproctis subflava)、舞毒蛾(Lymantria dispar)等,枯叶蛾科的天幕毛虫(Malacosoma neustria testacea)、赤松毛虫(Dendrolimus spectabilis)、落叶松毛虫(Dendrolimus superans)等,螟蛾科的斜纹隐斑螟(Crytoblabes loxiella)等,夜蛾科的黄地老虎(Agrotis segetum)等,卷蛾科的カラマツイトヒキハマキ(Ptycholoma lecheana circumclusana)、栗白小卷蛾(Cydia kurokoi)、スギカサガ(Cydia cryptomeriae)等,灯蛾科的黄领麻纹灯蛾(Spilosoma imparilis)、美国白蛾(Hyphantria cunea)等,微蛾科的シイモグリチビガ(Stigmella castanopsiella)等,刺蛾科的丽绿刺蛾(Parasa lepida)、球须刺蛾(Scopelodes contracus)、长须小刺蛾(Microleon longipalpis)等的成虫、幼虫及卵;
鞘翅目,例如金龟子科的红铜丽金龟(Anomala rufocuprea)、黑七鳃金龟(Heptophylla picea)等,吉丁科的白蜡窄吉丁(Agrilus spinipennis)等,天牛科的松墨天牛(Monochamus alternatus)等,叶甲科的肖钝角胸肖叶甲(Basilepta pallidula)等,象甲科的锈赤芦形象甲(Scepticus griseus)、马尾松角胫象(Shirahoshizo insidiosus)等,オサゾウムシ科(Dryophthoridae)的大褐象鼻虫(Sipalinus gigas)等,小蠹科的纵坑切梢小蠹(Tomicus piniperda)、イタヤノキクイムシ(Indocryphalus aceris)等,长蠢科的谷蠹(Rhizopertha dominica)等的成虫、幼虫及卵;
半翅目,例如蚜科的枞大蚜(Cinara todocola)等,球蚜科的鱼鳞云杉球蚜(Adelges japonicus)等,盾蚧科的柳杉圆盾蚧(Aspidiotus cryptomeriae)等,介壳虫科的角蜡蚧(Ceroplastes ceriferus)等的成虫、幼虫及卵;
膜翅目,例如叶蜂科的伊藤厚丝叶蜂(Pachynematus itoi)等,松叶蜂科的松黄叶蜂(Neodiprion sertifer)等,瘿蜂科的板栗瘿蜂(Dryocosmus kuriohilus)等的成虫、幼虫及卵;
双翅目,例如大蚊科的稻大蚊(Tipula aino)等,花蝇科的落叶松球果花蝇(Strobilomyia laricicola)等,瘿蚊科的柳杉瘿蚊(Contarinia inouyei)、マツシントメタマバエ(Contarinia matsusintome)等的成虫、幼虫及卵;
节肢动物门蛛形纲的蜱螨目,例如スギノハダニ(Oligonichus hondoensis)、针叶小爪螨(Oligonichus ununguis)等的成虫、幼虫及卵;
线虫动物门胞管肾纲垫刃目(Tylenchida),例如滑刃线虫科的松材线虫(Bursaphelenchus xylophilus)等。
本发明的化合物还可以用于内在地或外在地寄生于脊椎动物特别是恒温脊椎动物的牛、羊、山羊、马、猪、家禽、狗、猫、鱼等家畜或宠物的节肢动物类,线虫类,吸虫类,绦虫类,原生动物类的预防、治疗或防除。此外,作为成为对象的动物种类,除了上述之外,还包括小鼠、大鼠、仓鼠、松鼠等啮齿类,雪貂等食肉目,鸭、鸽子等禽类的宠物或实验动物等。作为具体的有害生物,可以举出节肢动物门昆虫纲的双翅目,例如虻科的ヤマトアブ(Tabanus rufidens)、金色虻(Tabanus chrysurus)等,蝇科的北栖家蝇(Musca bezzii)、家蝇(Musca domestica)、厩螫蝇(Stomoxys calcitrans)等,胃蝇科的肠胃蝇(Gasterophilus intestinalis)等,皮蝇科的牛皮蝇(Hypoderma bovis)等,狂蝇科的羊狂蝇(Oestrus ovis)等,丽蝇科的巨尾阿丽蝇(Aldrichina grahami)等,蚤蝇科的东亚异蚤蝇(Megaselia spiracularis)等,
鼓翅绳科的螫斑鼓翅蝇(Sepsis punctum)等,白蛉亚科的白斑蛾蚋(Telmatoscopus albipunctatus)、星斑蛾蚋(Psychoda alternata)等,蚊科的骚扰库蚊(Culex pipiens molestus)、淡色库蚊(Culex pipiens pallens)、中华按蚊(Anopheles sinensis)、コガタアカイエカ(Culex pipiens triaeniorhynchus summorosus)、白纹伊蚊(Ades albopictus)等,蚋科的一洼短蚋(Simulium iwatense)、キアシオオブユ(Prosimulium yezoense)等,蠓科的尖喙库蠓(Culicoides schulzei)、荒川库蠓(Culicoides arakawae)等的成虫、幼虫及卵;
隐翅目,例如蚤科的致痒蚤(Pulex irritans)、犬栉首蚤(Ctenocephalides canis)等的成虫、幼虫及卵;
虱目,例如海兽虱科的猪虱(Haematopinidae suis)、肉牛血虱(Haematopinidae eurysternus)等,啮毛虱科的牛毛虱(Damalinia bovis)等,毛虱科的牛颚虱(Linognathus vituli)等,短角鸟虱科的鸡虱(Menopon gallinae)等的成虫、幼虫及卵;
节肢动物门蛛形纲的蜱螨目,例如瓦螨科的雅氏瓦螨(Varroa jacobsoni),硬蜱科的长角血蜱(Haemaphysalis longicornis)、卵形硬蜱(Ixodes ovatus)、微小牛蜱(Boophilus microplus)、龟甲形钝眼蜱(Amblyomma testudinarium)等,巨刺螨科的トリサシダニ(Ornithonyssus sylvialum)等,皮刺螨科的鸡皮刺螨(Dermanyssus gallinae)等,蠕形螨科的猪蠕形螨(Demodex phylloides)等,疥螨科的牛疥螨(Sarcoptes scabiei bovis)、突变膝螨(Knemidocoptes mutans)等,痒螨科的耳痒螨(Otodectes cynotis)、羊痒螨(Psoroptes communis)等的成虫、幼虫及卵;
线虫动物门尾感器纲的圆线虫目,例如牛钩虫、猪肾虫、猪肺虫、毛圆线虫、辐射结节线虫等;
蛔虫目,例如猪蛔虫、鸡蛔虫等;
扁形动物门吸虫纲,例如日本血吸虫、肝片吸虫、鹿前后盘吸虫、卫氏并殖吸虫、日本卵圆前殖吸虫等;
原生动物门鞭毛虫纲的根足鞭毛虫目,例如组织滴虫属(Histomonas)等、原鞭毛虫目,例如利什曼虫(Leishmania)、锥虫属(Trypanosoma)等,多鞭毛虫目,例如贾第鞭毛虫属(Giardia)等,毛滴虫目,例如毛滴虫属(Trichomonas)等;
肉足虫纲的变形目,例如内变形属(Entamoeba)等;
孢子虫纲的焦虫亚纲,例如泰来虫属(Theilaria)、巴贝虫属(Babesia)等,晚生孢子虫亚纲,例如艾美虫属(Eimeria)、疟原虫属(Plasmodium)、弓形体属(Toxoplasma)等。
本发明的化合物还可以用于驱除对人体带来直接的危害或不快感的有害生物、或维持对于进行病原体的搬运或传播的有害生物的公共卫生状态。作为具体的有害生物,可以举出节肢动物门昆虫纲的鳞翅目,例如毒蛾科的モンシロドクガ(Sphrageidus similis)等,枯叶蛾科的波纹杂枯叶蛾(Kunugia undans)等,刺蛾科的褐边绿刺蛾(Parasa consocia)等,斑蛾科的马汀氏竹斑蛾(Artona martini)等,
鞘翅目,例如拟天牛科的沃黄拟天牛(Xanthochroa waterhousei)等,芫菁科的豆芫菁(Epicauta gorhani)等,隐翅虫科的毒隐翅虫(Paederus fuscipes)等,
膜翅目,例如胡蜂科的キイロスズメバチ(Vespa simillima xanthoptera)等,蚁科的中华短猛蚁(Brachyponera chinensis)等,蛛蜂科的环棒带蛛蜂(Batozonellus annulatus)等,
双翅目,例如蚊科的骚扰阿蚊(Armigeres subalbatus)等,蠓科的日本库蠓(Culicoides nipponensis)等,摇蚊科的羽摇蚊(Chironomus yoshimatsui)等,蚋科的樱花蚋(Simulium nikkoense)等,虻科的アオコアブ(Hirosia humilis)等,蝇科的家蝇(Musca domestica)等,厕蝇科的夏厕蝇(Fannia canicularis)等,丽蝇科的黑花蝇(Phormia regina)等,麻蝇科的褐尾麻蝇(Sarcophaga peregrina)等的成虫、幼虫及卵;
隐翅目,例如蚤科的致痒蚤(Pulex irritans)等的成虫、幼虫及卵;
蜚蠊目,例如姬蜚蠊科的德国小蠊(Blattella germanica)等,蜚蠊科的美洲大蠊(Periplaneta americana)、黑胸大蠊(Periplaneta fuliginosa)、日本大蠊(Periplaneta japonica)等的成虫、幼虫及卵;
直翅目(Orthoptera),例如蟋螽科的突灶螽(Diestrammena japonica)、カマドウマ(Diestrammena apicalis)等的成虫、幼虫及卵;
虱目,例如人虱科的体虱(Pediculus humanus humanus)等、阴虱科的阴虱(Phthirius pubis)等的成虫、幼虫及卵;
半翅目,例如臭虫科的温带臭虫(Cimex lectularius)等,猎蝽科的褐菱猎蝽(Isyndus obscurus)的成虫、幼虫及卵;
节肢动物门缺尾纲的弹尾目(Collembola),例如紫跳虫科的紫跳虫(Hypogastrura communis)等的成虫、幼虫及卵;
节肢动物门蛛形纲的蜱螨目,例如硬蜱科的全沟硬蜱(Ixodes persulcatus)等,巨刺螨科的柏氏禽刺螨(Ornithonyssus bacoti)等,肉食螨科的南爪螨(Chelacaropsis moorei)等,蒲螨科的球腹蒲螨(Pyemotes ventricosus)等、蠕形螨科的毛囊蠕形螨(Demodex folliculorum)等,蚍螨科的屋尘螨(Dermotophagoides pteronyssinus)等,疥螨科的疥螨(Sarcoptes scabiei)等,恙螨科的红恙螨(Trombicula akamushi)等的成虫、幼虫及卵;
蜘蛛目,例如管巢蛛科的日本红螯蛛(Chiracanthium japonicum)等,巨蟹蛛科的白额巨蟹蛛(Heteropoda venatoria)等,幽灵蛛科的广六眼幽灵蛛(Spermophora senoculata)、家幽灵蛛(Pholcus phalangioides)等,壁线蛛科的华南壁钱(Uroctea compactilis)等,跳蛛科的黑色蝇虎(Plexippus paykulli)、ミスジハエトリ(Plexippus adansoni)等的成虫、幼虫及卵;
蝎目,例如钳蝎科的黄斑蝎(Isometrus europaeus)等的成虫、幼虫及卵;
节肢动物门唇足纲的蜈蚣目,例如蜈蚣科的少棘蜈蚣(Scolopendra subspinipes mutilans)、日本棘蜈蚣(Scolopendra subspinipes japonica)等的成虫、幼虫及卵;
蚰蜒目,例如蚰蜓科的蚰蜓(Thereuronema hilgendofi)等的成虫、幼虫及卵;
节肢动物门倍足纲的带马陆目,例如奇马陆科的温室马陆(Oxidus gracilis)等的成虫、幼虫及卵;
节肢动物门甲壳纲的等足目,例如鼠妇科的鼠妇虫(Porcellio scaber)等的成虫、幼虫及卵;
环节动物门蛭纲的颚蛭目,例如山蛭科的日本山蛭(Haemadipsa zeylanica japonica)等。
本发明的化合物对于防除对农作物、天然林、人工林以及都市绿地的树木或观赏植物带来损害的有害生物,例如节肢动物类、腹足类、线虫类特别有价值。这种情况下,本发明的化合物可以以它们的商业制剂及通过这些制剂制备的使用形态,以与其它的活性化合物,例如杀虫剂、杀螨剂、杀线虫剂、杀菌剂、增效剂、植物调整剂、毒饵或除草剂的混合剂方式存在。
作为使用形态,可以采用可湿性粉剂、颗粒可湿性粉剂、水溶剂、乳剂、液体剂、水中悬浮剂·水中乳浊剂等易流动剂(flowable agent)、胶囊剂、粉剂、颗粒剂、饵剂、气雾剂等。这些制剂中,本发明的化合物的总含量通常为0.001~95质量%、优选为0.1~60质量%。
为了防除节肢动物类、腹足类、线虫类,通常对由于这些有害生物而产生灾害的场所或有可能产生灾害的场所,除了对植物的茎叶部撒布之外,还可以进行土壤全层混合、垄沟施用、床土混合、穴盘苗()处理、植穴处理、根部()处理、施顶肥、稻箱处理、水面施用等对土壤等进行处理而从根吸收来使用。此外,还可以通过种子浸渍在药剂中、拌种()、过氧化钙处理()等种子处理,培养液(水栽)栽培中的对培养液的施用、烟熏或注入树干等来使用。
根据使用的情况、有害生物的种类、发生量及成为对象的作物·树木的种类或栽培形态·生长状态不同而不同,通常每10公亩以本发明的化合物量计施用0.1~1000g、优选1~100g。对其处理时,对于可湿性粉剂、颗粒可湿性粉剂、水溶剂、乳剂、液体剂、水中悬浮剂·水中乳浊剂等易流动剂、胶囊剂等,用水进行稀释,虽然根据对象植物的种类或栽培形态·生长状态不同而不同,但是通常以每10公亩10~1000升的施用量对作物等进行撕布即可。此外,对于粉剂或气雾剂,以其制剂的状态对作物等进行处理即可。
作为成为对象的有害生物主要在土壤中加害植物的情况、从根部吸收药剂来防除成为对象的有害生物的情况的施用方法,可以举出例如,将制剂稀释在水中或不稀释来对植物体的根部或育苗用苗床等施用的方法,将颗粒剂撕布到植物体的根部或育苗用苗床等的方法,在播种前或移植前撕布粉剂、可湿性粉剂、颗粒可湿性粉剂、颗粒剂等而与全部土壤混合的方法,在播种前或种植植物体前,向植穴、垄沟等撕布粉剂、可湿性粉剂、颗粒可湿性粉剂、颗粒剂等的方法等。
对于可湿性粉剂、颗粒可湿性粉剂、水溶剂、乳剂、液体剂、水中悬浮剂·水中乳浊剂等易流动剂、胶囊剂等,用水稀释,通常以每10公亩5~500升的施用量,对处理的全部区域均匀地对土壤表面进行撕布或向土壤中灌注,对于粉剂、颗粒剂或饵剂等,以该制剂的状态,对处理的全部区域均匀地撕布到土壤表面即可。撕布或灌注还可以在要保护的种子或作物·树木的周围进行。此外,还可以在撕布中或撕布后进行耕耘,机械性地分散有效成分。
作为对水稻的育苗箱的施用方法,剂型根据播种时施用、绿化期施用、移植时施用等施用时期不同而有可能不同,例如可以以粉剂、颗粒可湿性粉剂、颗粒剂等剂型施用。还可以通过与培土混合来施用,培土与粉剂、颗粒可湿性粉剂或颗粒剂等的混合,例如可以进行床土混合、覆土混合、对全部培土的混合等。此外,还可以使培土和各种制剂交替形成层状来施用。
作为对水田的施用方法,通常将大粒剂()、袋剂、颗粒剂、颗粒可湿性粉剂等固体制剂,易流动剂、乳剂等液体状制剂撕布到积水状态的水田中。此外,插秧()时,还可以将适当的制剂直接或与肥料等混合来撕布、注入到土壤中。此外,在水口或灌溉装置等水向水田流入的流入源利用乳剂、易流动剂等药液,由此可以伴随着水的供给来省力地施用。
作为种子处理的方法,可以举出例如,将液态或固体状的制剂稀释或不稀释地以液体状态浸渍种子来附着、浸渗药剂的方法,将固体制剂或液态制剂与种子混合、进行拌种处理来附着在种子的表面上的方法,与树脂、聚合物等附着性的载体混合来对种子进行涂布的方法,栽插的同时撕布到种子附近的方法等。进行该种子处理的“种子”指的是在植物的繁殖中使用的栽培初期的植物体,除了种子之外,还可以举出例如球根、块茎、种薯、珠芽、鳞芽、鳞茎或插枝栽培用的营养繁殖用植物体。此外,施用时的植物的“土壤”或“栽培载体”表示用于栽培作物的支撑体、特别是使根生长的支撑体,对材质不特别限定,若为植物可以生长的材质即可,可以为所谓的土壤、育苗垫、水等,作为具体的原材料,可以举出例如砂、浮石、蛭石、硅藻土、琼脂、凝胶状物质、高分子物质、岩棉、玻璃棉、木材屑、树皮等。
作为进行移植的栽培植物的播种、育苗期的处理,除了对种子的直接处理之外,优选对育苗用苗床进行液态药剂的灌注处理或颗粒剂的撕布处理。此外,定植时使用颗粒剂对植穴进行处理或与移植场所附近的栽培载体混合也为优选的处理。
本发明的化合物对于保护木材(立木、倒树、加工木材、贮藏木材或结构木材)不受白蚁类或甲虫类等的加害来说也具有价值。这种情况下,可以通过对木材或其周围的土壤等进行油剂、乳剂、可湿性粉剂、凝胶剂的撕布·注入·灌注·涂布,粉剂、颗粒剂等的撕布等方法来防除。此外,本情况下使用的油剂、乳剂、可湿性粉剂、粉剂等还可以以与其它的活性化合物,例如杀虫剂、杀螨剂、杀线虫剂、杀菌剂、忌避剂或增效剂的混合剂方式存在,这些制剂中,本发明的化合物的总含量为0.0001~95质量%,对于油剂、粉剂或颗粒剂,优选含有0.005~10质量%,对于乳剂、可湿性粉剂及凝胶剂,优选含有0.01~50质量%。防除白蚁类或甲虫类时,以每1m2有效成分化合物量为0.01~100g来撕布在土壤或木材表面上。
本发明的化合物,将谷类、果实、树木的果实、香辣料及烟等制品以其原来的状态、形成粉末的状态或混入到制品中的状态贮藏时,可以保护它们不受鳞翅目类、甲虫类、蜱螨类的加害。此外,将动物制品(皮、毛、羊毛和羽毛等)或植物制品(棉、纸等)以天然或转化的状态贮藏时,也可以保护它们不受鳞翅目类、甲虫类、蠹虫类或蟑螂类等的攻击,进而贮藏肉或鱼等食品时可以保护它们不受鳞翅目类、甲虫类、双翅类、蜱螨类等的攻击。这种情况下,可以通过油剂、乳剂、可湿性粉剂、粉剂等的撕布,树脂蒸散剂等的设置,薰剂或烟雾剂的处理,颗粒、片剂和毒饵的设置,气雾剂的喷雾等方法来进行防除。此外,这些制剂还可以以与其它的活性化合物,例如杀虫剂、杀螨剂、杀线虫剂、杀菌剂、忌避剂或增效剂的混合剂方式存在,这些制剂中,本发明的化合物的总含量可以为0.0001~95质量%。
本发明的化合物对于寄生于人及家畜的体表、摄食皮肤或吸血等有直接危害的节肢动物类,使人及家畜的疾病蔓延、作为这种疾病的传播者的节肢动物类、线虫类、吸虫类、绦虫类、原生动物类,给人类带来不快感的节肢动物类的驱除或预防有价值。这种情况下,本发明的化合物可以少量混入到食物或饲料等中,以可以适当地经口摄取的配制药剂组合物等,例如含有可药用的载体、包衣物质的片剂、丸剂、胶囊剂、糊、凝胶、饮料、药用饲料、药用饮料水、药用追饵()、缓释性大粒丸剂、其它使得保留在胃肠道内的缓释性装置等方式经口给药,或以喷雾、粉末、油脂、乳膏、软膏、乳剂、洗剂、喷滴剂(spot-on)、浇泼剂(pour-on)、洗发剂等方式经皮给药。为了达成这种效果,通常本发明的化合物可以给予0.0001~0.1质量%,优选为0.001~0.01质量%。而且,作为经皮给药、局部给药的方法,还可以利用安装到动物上的装置(例如项圈、徽章或耳标等)以局部性地或全身性地防除节肢动物。
对使用本发明的化合物作为对于家畜、宠物等动物或人的驱虫剂时的具体的经口给药方法及经皮给药方法进行说明,但是未必限于此。
以药用饮料水方式经口给药时,饮料为与普通膨润土等悬浮剂、润湿剂或其它的赋型剂一起在适当的非毒性的溶剂或水中的溶解、悬浮液或分散液。通常饮料还含有消泡剂。饮料处方通常可以含有本发明的化合物0.01~1.0质量%,优选含有0.01~0.1质量%。
希望以干燥的个体的单元使用形态口服给药时,使用含有通常规定量的有效成分的胶囊、丸剂或片剂。这些使用形态通过与适当地将活性成分细粉碎的稀释剂、填充剂、崩解剂和/或粘合剂,例如淀粉、乳糖、滑石、硬脂酸镁、植物性橡胶等均质混合来制备。这种单元使用处方可以根据治疗的宿主动物的种类、感染的程度以及寄生虫的种类及宿主的体重在宽的范围内改变驱虫剂的质量和含量。
通过动物饲料给药时,可以以颗粒方式将其均质分散在饲料中、或用作顶肥来使用。为了达成一般优选的抗寄生虫效果,最终饲料中还可以含有本发明的化合物例如0.0001~0.05质量%、优选0.0005~0.01质量%。
溶解或分散在液体载体赋型剂中而成的药剂可以通过前胃内、肌肉内、气管内或皮下注射非经口地给予动物。为了非经口给予,活性化合物优选与花生油、棉籽油等适当的植物油混合。这种处方通常可以含有本发明的化合物0.05~50质量%、优选0.1~5.0质量%。
此外,可以通过与二甲基亚砜、烃溶剂等适当的载体混合来局部给药。该制剂通过喷雾或直接注加来直接适用于动物的外部表面。
此外,本发明的化合物,也可以作为产生直接危害的节肢动物类或作为疾病的传播者的节肢动物类等的驱虫剂,对于这些有害生物可能潜在的周围环境,通过油剂、乳剂、可湿性粉剂等的撕布·注入·灌注·涂布,粉剂等的撕布,薰蒸剂、蚊香·自燃烧型薰烟剂、化学反应型烟雾剂等加热烟雾剂,雾化剂等薰烟剂,ULV剂等的处理,颗粒、片剂和毒饵的设置,或漂浮的粉剂、颗粒剂等向水路、井、贮水池、贮水槽及其它的流水或停留水中的滴加等方法利用。进一步地,农业、森林害虫中,对于一些毒蛾等,可以与上述方法同样地防除,对于蝇类等,混入到家畜的饲料中并混入到粪中的方法是有效的,对于蚊类等,在电蚊香器等中挥散到空中的方法等是有效的。而且,这些使用形态的制剂,还可以以与其它的活性化合物,例如杀虫剂、杀螨剂、杀线虫剂、杀菌剂、忌避剂或增效剂的混合剂方式存在,这些制剂中,本发明的化合物的总含量例如为0.0001~95质量%是适当的。
本发明的化合物还可以以与其它的活性化合物的混合剂方式存在。特别是通过与具有杀虫活性、杀螨活性或杀线虫活性的化合物(杀虫剂)混合来使用,对于对植物带来损害的节肢动物类、腹足类、线虫类等有害生物的防除,可以扩大防除对象病害虫,还可以期待药量的降低等协同效果等。作为该具体例的活性化合物,可以举出有机磷剂,例如谷硫磷(azinphos-methyl)、乙酰甲胺磷(acephate)、毒死蜱(chlorpyrifos)、二嗪磷(daizinon)、敌敌畏(dichlorvos)、甲基内吸磷(dimeton-S-methyl)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、乙拌磷(disulfoton)、乙硫磷(ethion)、杀螟松(fenitrothion)、倍硫磷(fenthion)、异唑磷(isoxathion)、马拉硫磷(malathion)、甲胺磷(methamidophos)、杀扑磷(methidathion)、久效磷(monocrotophos)、二溴磷(naled)、オキシデプロホス(oxideprofos)、对硫磷(parathion)、稻丰散(phenthoate)、伏杀磷(phosalone)、甲嘧硫磷(pirimiphos-methyl)、哒嗪硫磷(piridafenthion)、丙溴磷(profenofos)、丙硫磷(prothiofos)、丙虫磷(propaphos)、吡唑硫磷(pyraclofos)、水杨硫磷(salithion)、硫丙磷(sulprofos)、甲基乙拌磷(thiometon)、杀虫畏(tetrachlorvinfos)、敌百虫(trichlorphon)、蚜灭多(vamidothion)等;
氨基甲酸酯剂,例如棉铃威(alanycarb)、恶虫威(bendiocarb)、丙硫克百威(benfuracarb)、甲萘威(carbaryl)、虫螨威(carbofuran)、呋喃威(carbosulfan)、杀虫丹(ethiofencarb)、仲丁威(fenobucarb)、呋线威(furathiocarb)、异丙威(isoprocarb)、灭多虫(methomyl)、速灭威(metolcarb)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)等;
有机氯剂,例如艾氏剂(aldrin)、氯丹(chlordane)、DDT(p,p’-DDT)、硫丹(endosulfan)、林丹(lindane)等;
拟除虫菊酯剂,例如氟丙菊酯(acrinathrin)、丙烯菊酯(allethrin)、联苯菊酯(bifenthrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、三氟氯氰菊酯(cyhalothrin)、苯醚氰菊酯(cyphenothrin)、氯氰菊酯(cypermethrin)、溴氰菊酯(deltamethrin)、醚菊酯(ethofenprox)、甲氰菊酯(fenpropathrin)、氰戊菊酯(fenvalerate)、氟氰戊菊酯(flucythrinate)、三氟醚菊酯(flufenprox)、氟胺氰戊菊酯(fluvalinate)、炔呋菊酯(furamethrin)、苄螨醚(halfenprox)、炔醚菊酯(imiprothrin)、苄氯菊酯(permethrin)、苯醚菊酯(phenothrin)、炔丙菊酯(prallethrin)、除虫菊酯(pyrethrins)、苄呋菊酯(resmethrin)、氟硅菊酯(silafluofen)、七氟菊酯(tefluthrin)、四溴菊酯(tralomethrin)、四氯菊酯(transfluthrin)等;
新烟碱剂,例如啶虫脒(acetamiprid)、可尼丁(clothianidin)、呋虫胺(dinotefran)、吡虫啉(imidacloprid)、烯啶虫胺(nitenpyram)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)等;
苯基苯甲酰脲剂等的昆虫成长控制剂,例如定虫隆(chlorfluazuron)、除虫脲(diflubenzuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、氯芬奴隆(lufenuron)、氟酰脲(novaluron)、氟苯脲(teflubenzuron)、杀铃脲(triflumuron)、稻虱净(buprofezin)、环虫酰肼(chromafenozide)、氯虫酰肼(halofenozide)、甲氧虫酰肼(methoxyfenozide)、虫酰肼(tebufenozide)、环丙氨嗪(cyromazine)等;
保幼激素剂,例如苯虫醚(diofenolan)、苯氧威(fenoxycarb)、烯虫乙酯(hydroprene)、烯虫酯(methoprene)、吡丙醚(pyriproxyfen)等;
由微生物产生的杀虫性物质等,例如阿巴克丁(abamectin)、甲氨基阿维菌素(emamectin-benzoate)、双氢除虫菌素(ivermectin)、レピメクチン(lepimectin)、密灭汀(milbemectin)、奈马克丁(nemadectin)、日光霉素(Nikkomycin)、スピネトラム(spinetram)、多杀菌素(spinosad)、BT剂等;
来自天然物的杀虫性物质等,例如新烟碱(anabasine)、印楝素(azadiractin)、鱼藤素(deguelin)、辛癸酸甘油酯(decanolyoctanoylglycerol)、羟丙基淀粉(hydroxypropylstarch)、大豆卵磷脂(lecithin)、レピメクチン(lepimectin)、烟碱(nicotine)、降烟碱(nornicotine)、油酸钠(oreic acid sodium salt)、石油油料(petroleum oil)、丙二醇单月桂酸酯(propylene glycol monolaurate)、菜油(rape oil)、鱼藤酮(rotenone)等;
其它的杀虫剂,例如乙酰虫腈(acetoprole)、杀虫磺(bensultap)、巴丹(cartap)、杀虫环(chiocyclam)、氯虫酰胺(chlorantraniliprore)、溴虫腈(chlorfenapyr)、丁醚脲(diafenthiuron)、乙虫清(ethiprole)、氟虫腈(fipronil)、氟啶虫酰胺(flonicamid)、氟虫双酰胺(flubenziamid)、氟蚁腙(hydramethylnon)、茚虫威(indoxacarb)、氰氟虫腙(metaflumizone)、聚乙醛(metaldehyde)、硫酸烟碱(nicotin sulfate)、吡蚜酮(pymetrozine)、啶虫丙醚(pyridalyl)、ピリフルキナゾン(pyrifluquinqzon)、螺虫乙酯(spirotetramat)、唑虫酰胺(tolfenpyrad)、唑蚜威(triazamate)等;
杀螨剂,例如灭螨醌(acequinocyl)、阿米曲拉(amitraz)、三唑锡(azocyclotin)、苯螨特(benzoximate)、联苯肼酯(bifenazate)、乐杀螨(binapacryl)、溴螨酯(bromopropylate)、灭螨猛(chinomethionat)、四螨嗪(clofentezine)、杀螨剂(cyenopyrafen)、丁氟螨酯(cyflumetofen)、三环锡(cyhexatin)、三氯杀满醇(dicofol)、除螨灵(dienochlor)、乙螨唑(ethoxazole)、抗螨唑(fenazaflor)、喹螨醚(fenazaquin)、六苯丁锡氧(fenbutatin oxide)、苯硫威(fenothiocarb)、唑螨酯(fenpyroximate)、嘧螨酯(fluacrypyrim)、噻螨酮(hexythiazox)、ピリミジフェン(pirimidifen)、ポリナクチン複合体(polynactins)、克螨特(propargite)、达蟥酮(pyridaben)、螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)、吡螨胺(tebufenpyrad)、三氯杀螨砜(tetradifon)等;
杀线虫剂,例如磷化铝(aluminium phosphide)、ベンクロトラズ(benclothiaz)、硫线磷(cadusafos)、灭线磷(ethoprophos)、噻唑磷(fosthiazate)、新烟碱类(imicyafos)、盐酸左旋咪唑(levamisol hydrochloride)、倍硫磷亚砜(mesulfenfos)、安百亩(metam-ammonium)、甲基异硫氰酸甲酯(methyl isothiocyanate)、酒石酸モランテル(moranteltartarate)、杀线威(oxamyl)等;
毒饵,例如氯鼠酮(chlorphacinone)、杀鼠迷(coumatetralyl)、敌鼠(diphacinone)、氟乙酸钠(sodium fluoracetate)、杀鼠灵(warfarin)等。
本发明的化合物还可以以与具有杀虫活性、杀螨活性或杀线虫活性的化合物以外的其它活性化合物的混合剂方式存在。为了防除在使用时期同时产生的病害和/或杂草,通过与具有杀菌活性、除草活性或植物成长调整活性的化合物混合来使用,防除劳力降低的同时还可以期待药量的降低等协同效果。此外,通过与忌避剂或增效剂等混合来使用,可以期待协同效果等更有效的防除效果。
作为这种活性化合物,具体地说,可以举出杀菌剂,例如D-D(1,3-二氯丙烯、1,3-dichloropropene)、苯并噻二唑(acibenzolar-S-methyl)、吲唑磺菌胺(amisulbrom)、敌菌灵(anilazine)、嘧菌酯(azoxystrobin)、碱式硫酸铜(basic copper sulfate)、苯菌灵(benomyl)、苯噻菌胺(benthiavalicarb-isopropyl)、苯噻硫氰(benthiazole)、联苯三唑醇(bitertanol)、杀稻瘟菌素S (blasticidin S)、啶酰菌胺(boscalid)、糠菌唑(bromuconazole)、碳酸钙(calcium carbonate)、石硫合剂(calcium polysulfide)、克菌丹(captan)、多菌灵(carbendazim)、环丙酰亚胺(carpropamid)、灭螨猛(chinomethionat)、地茂散(chloroneb)、三氯硝基甲(chloropicrin)、百菌清(chlorothalonil)、DBEDC(胺磺铜、complex of bis(ethylenediamine)copper-bis-(dodecylbenzenesulfonic acid))、氢氧化铜(copper hydroxide)、壬基苯酚磺酸铜(copper nonylphenol sulfonate)、碱式氯化铜(copper oxychloride)、氰霜唑(cyazofamid)、环氟菌胺(cyflufenamid)、霜脲氰(cymoxanil),
环唑醇(cyproconazole)、嘧菌环胺(cyprodinil)、棉隆(dazomet)、抑菌灵(dichlofluanid)、双氯氰菌胺(diclocymet)、哒菌酮(diclomezine)、乙霉威(diethofencarb)、苯醚甲环唑(difenoconazole)、二氟林(diflumetorim)、烯酰吗啉(dimethomorph)、代森铵(dithane-stainless)、二噻农(dithianon)、多果定(dodine)、氯唑灵(echlomezole)、克瘟散(edifenphos)、蘑菇提取物(extract from mushroom)、咪唑菌酮(fenamidone)、氯苯嘧啶醇(fenarimol)、腈苯唑(fenbuconazole)、环酰菌胺(fenhexamid)、氰菌胺(fenoxanol)、嘧菌腙(ferimzone)、氟啶胺(fluazinam)、氟酰菌胺(flumetover)、氟吡菌胺(fluopicolide),
氟酰亚胺(fluoroimide)、氟喹唑(fluquinconazole)、磺菌胺(flusulfamide)、氟酰胺(flutolanil)、三乙膦酸铝(fosetyl-AL)、四氯苯酞(fthalide)、咯菌腈(fuldioxonil)、呋吡菌胺(furametpyr)、呋菌唑(furconazole)、己唑醇(hexaconazole)、ヒドロキシイソキサゾール(hydroxyioxazole)、恶霉灵(hymexazol)、酰胺唑(imibenconazole)、双胍辛酸三乙酸酯(iminoctadine acetate)、双胍辛胺-DBS(iminoctadine-DBS)、种菌唑(ipconazole)、IBP(异稻瘟净、iprobenfos)、异菌脲(iprodione)、异丙菌胺(iprovalicarb)、稻瘟灵(isoprothiolane)、春日霉素(kasugamycin)、醚菌酯(kresoxim-methyl)、代森锰锌(mancozeb)、代森锰(maneb)、代森锰锌(manzeb)、嘧菌胺(mepanipyrim),
担菌宁(mepronil)、甲霜灵(metalaxyl)、安百亩(metam-ammonium)、威百亩(metam-sodium)、叶菌唑(metconazole)、磺菌威(methasulfocarb)、溴甲烷(methyl bromide)、异硫氰酸甲酯(methylisothiocyanate)、苯氧菌胺(metominostrobin)、灭粉霉素(mildiomycin)、腈菌唑(myclobutanil)、福美镍(nickel dimethyldithiocarbamate)、肟醚菌胺(orysastrobin)、霜灵(oxadixyl)、喹啉铜(oxine-copper)、奥索利酸(oxolinic acid)、咪唑富马酸盐(oxpoconazole fumarate)、氧化萎锈灵(oxycarboxin)、土霉素(oxytetracycline)、克草猛(pebulate)、稻瘟酯(pefurazoate)、戊菌隆(pencycuron)、吡噻菌胺(penthiopyrad)、代森福美锌(polycarbamate)、多抗霉素B(polyoxin-B),
多氧霉素类(polyoxins)、碳酸氢钾(potassium hydrogen carbonate)、噻菌灵(probenazole)、咪鲜安(prochloraz)、腐霉利(procymidone)、霜霉威(propamocarb)、丙环唑(propiconazole)、甲基代森锌(propineb)、吡唑醚菌酯(pyraclostrobin)、吡菌磷(pyrazophos)、啶斑肟(pyrifenox)、嘧霉胺(pyrimethanil)、咯奎酮(pyroquilon)、五氯硝基苯(quintozene)、银(silver)、硅氟唑(simeconazole)、碳酸氢钠(sodium hydrogen carbonate)、次氯酸钠(sodium hypochlorite)、葚孢菌素(spiroxamine)、链霉素(streptomycin)、硫(sulfur)、戊唑醇(tebuconazole)、叶枯酞(tecloftalam)、氟醚唑(tetraconazole)、噻菌灵(thiabendazole)、代森环(thiadiazin)、噻氟菌胺(thifluzamide)、托布津(thiophanate)、甲基硫菌灵(thiophanate-methyl)、福美双(thiram)、噻酰菌胺(tiadinil)、甲基立枯磷(tolclofos-methyl)、对甲抑菌灵(tolylfluanid)、三唑酮(triadimefon)、三唑醇(triadimenol)、三环唑(tricyclazole)、肟菌酯(trifloxystrobin),
氟菌唑(triflumizole)、嗪胺灵(triforine)、灭菌唑(triticonazole)、井冈霉素(validamycin(-A))、烯菌酮(vinclozolin)、硫酸锌(zinc sulfate)、代森锌(zineb)、福美锌(ziram)等。
作为具有除草活性的化合物,可以举出例如苯草醚(aclonifen)、三氟羧草醚钠盐(acifluofe n-sodium)、甲草胺(alachlor)、禾草灭(alloxydim)、氨唑草酮(amicarbazone) 、酰嘧磺隆(amidosulfuron)、莎稗磷(anilofos)、黄草灵(asulam)、莠去津(atrazine)、四唑嘧磺隆(azimsulfuron)、呋草黄(benfuresate)、苄嘧磺隆(bensulfuron-methyl)、噻草平(bentazone)、杀草丹(benthiocarb)、苯并双环酮(benzobicyclon)、吡草酮(benzofenap)、双丙氨膦(bialaphos) 、治草醚(bifenox) 、溴丁酰草胺(bromobutide)、溴苯腈(bromoxynil)、抑草磷(butamifos)、苯酮唑(cafenstrole)、过氧化钙(calcium peroxide)、长杀草(carbetamide)、醚磺隆(cinosulfuron)、氯甲酰草胺(clomeprop)、环丙嘧磺隆(cyclosulfamuron)、氰氟草酯(cyhalofop-butyl)、杀草隆(daimuron)、甜菜安(desmedipham)、禾草灵(diclofop-methyl),
吡氟草胺(diflufenican)、唑隆(dimefuron)、异戊乙净(dimethametryn)、特乐酚(dinoterb)、敌草快(diquat)、敌草隆(diuron)、禾草畏(esprocarb)、乙嗪草酮(ethiozin)、乙呋草黄(ethofumesate)、乙氧嘧磺隆(ethoxysulfuron)、乙氧苯草胺(etobenzanid)、精唑禾草灵(fenoxaprop-P-ethyl)、四唑草胺(fentrazamide)、氟酮磺隆(flucarbazone)、氟噻草胺(flufenacet)、呋草酮(flurtamone)、嗪草酸甲酯(fluthiacet-methyl) 、甲酰胺磺隆(foramsulfuron)、草铵膦(glufosinate-ammonium)、草甘膦异丙胺盐(glyphosate-isopropyl amine)、草甘膦三甲基硫盐(glyphosate-trimesium)、灭草烟(imazapyr)、咪唑磺隆(imazosulfuron),
茚草酮(indanofan)、碘磺隆(iodosufluron)、辛酰碘苯腈(ioxynil-octanoate)、异丙隆(isoproturon)、双苯唑酸(isoxadifen)、异唑草酮(isoxaflutole)、乳氟禾草灵(lactofen)、利谷隆(linuron) 、苯噻草胺(mefenacet)、磺胺磺隆(mesosulfuron)、苯嗪草酮(metamitron)、噻唑隆(methabenzthiazuron)、磺草唑胺(metosulam)、嗪草酮(metribuzin)、敌草胺(napropamide)、草不隆(neburon)、炔草酮(oxadiargyl)、草酮(oxadiazon)、嗪草酮(oxaziclomefone)、百草枯(paraquat)、二甲戊乐灵(pendimethalin)、环戊草酮(pentoxazone)、苯敌草(phenmedipham)、丙草胺(pretilachlor)、丙苯磺隆(propoxycarbazone)、苄草丹(prosulfocarb)、双唑草腈(pyraclonil)、吡草醚(pyraflufe n-ethyl)、吡唑特(pyrazolate)、吡嘧磺隆(pyrazosulfuro n-ethyl)、稗草畏(pyributicarb)、环酯草醚(pyriftalid)、嘧草醚(pyriminobac-methyl)、喹禾灵(quizalofop-ethyl)、稀禾定(sethoxydim)、西玛津(simazine)、磺草酮(sulcotrion)、磺酰唑草酮(sulfentrazone)、甲氧噻草胺(thenylchlor)、三嗪氟草胺(triaziflam)、脱叶磷(tribufos)等。
此外,作为具有植物成长调节作用的化合物,例如可以与1-萘基乙酰胺(1-naphthylacetic acid)、4-CPA(4-CPA)、6-苄氨基嘌呤(6-benzylaminopurine)、丁乐灵(butralin)、氯化钙(calcium chloride)、甲酸钙(calcium formate)、过氧化钙(calcium peroxide)、硫酸钙(calcium sulfate)、矮壮素(chlormequat chloride)、胆碱(choline)、氨腈(cyanamide)、环丙酰胺(cyclanilide)、丁酰肼(daminozide)、癸醇(decyl alcohol)、滴丙酸(dichjoprop)、乙烯磷(ethephon)、吲唑酯(ethychlozate)、呋嘧醇(flurprimidol)、吡效隆(forclorfenuron)、赤霉酸(gibberellic acid)、吲哚丁酸(indolebutyric acid)、马来酰肼钾盐(maleic hydrazide potassium salt)、吡唑解草酯(mefenpyr)、甲哌啶(mepiquat chloride)、8-羟基喹啉硫酸盐(oxine sulfate, 8-hydroxyquinoline sulfate)、多效唑(paclobutrazol)、石蜡(paraffin)、调环酸钙盐(prohexadione-calcium)、茉莉酮(prohydrojasmon)、噻苯隆(thidiazuron)、抗倒酯(trinexapac)、烯效唑P(uniconazole-P)、蜡(wax)等混合来使用。
忌避剂,可以举出例如辣椒素(capsaicin)、蒈烷-3,4-二醇(carane-3,4-diol)、香茅醛(citronellal)、避蚊胺(deet)、邻苯二甲酸二甲酯(dimethyl phthalate)、日扁柏素(hinokitiol)、柠檬烯(limonene)、芳樟醇(linalool)、薄荷醇(menthol)、薄荷酮(menthone)、萘(naphthalene)、二硫四甲秋兰姆(thiram)等;
增效剂,可以举出例如亚甲基二羟基萘(methylenedioxynaphthalene)、萘基丙炔基醚(naphthyl propynyl ether)、硝基苄基硫氰酸酯(nitrobenzyl thiocyanate)、八氯二丙醚(octachlorodipropyl ether)、戊炔基邻苯二甲酰亚胺(pentynyl phthalimide)、フェニル·サリオクソン(phenyl salioxon)、胡椒基丁醚(piperonil butoxide)、黄樟油精(safrole)、增效菊(sesamex)、芝麻素(sesamin)、亚砜(sulfoxide)、磷酸三苯脂(triphenyl phosphate)、增效炔醚(verbutin)等。
本发明中,例如通过与质型多角体病毒(Cytoplasmic polyhedrosis virus、CPV)或、昆虫痘病毒(Entomopox virus、EPV)、颗粒体症病毒(Granulosis virus、GV) 、核型多角体病毒(Nuclear polyhedrosis virus、NPV)等的病毒制剂,球孢白僵菌(Beauveria bassiana)、布氏白僵菌(Beauveria brongniartii)、瘤捕单顶孢(Monacrosporium phymatophagum)、玫烟色拟青霉(Paecilomyces fumosoroseus)、穿刺巴氏杆菌(Pasteuria penetrans)、虫生线虫(Steinernema carpocapsae)、格氏线虫(Steinernema glaseri)、斯氏线虫(Steinernema kushidai)、蜡蚧轮枝菌(Verticillium lecanii)等作为杀虫或杀线虫剂使用的微生物农药,放射形土壤杆菌(Agrobacterium radiobactor)、枯草芽胞杆菌(Bacillus subtilis)、胡萝卜软腐欧文菌(Erwinia carotovora)、非病原性尖孢镰刀菌(Fusarium oxysporum)、假单胞菌属CAB-02(Pseudomonas CAB-02)、荧光假单胞菌(Pseudomonas fluorescens)、踝节菌属(Talaromyces)、深绿木霉(Trichoderma atroviride)、木素木霉(Trichoderma lignorum)等作为杀菌剂使用的微生物农药,野油菜黄单胞菌(Xanthomonas campestris)等作为除草剂使用的生物农药等混合来使用,可以期待同样的效果。
进一步地,作为生物农药,例如还可以与加州钝绥螨(Amblyseius californicus)、黄瓜钝绥螨(Amblyseius cucumeris)、不纯钝绥螨(Amblyseius degenerans)、科曼尼蚜茧蜂(Aphidius colemani)、食蚜瘿蚊(Aphidoletes aphidimyza)、草蛉(Chrysoperia carnea)、西伯利亚离颚茧蜂(Dacnusa sibirica)、潜蝇姬小蜂(Diglyphus isaea)、丽蚜小蜂(Encarsia formosa)、浆角蚜小蜂(Eretmocerus eremicus)、细腰凶蓟马(Franklinothrips vespiformis)、异色瓢虫(Harmonia axyridis)、异角亨姬小蜂(Hemiptarsenus varicornis)、丽潜蝇姬小蜂(Neochrysocharis formosa)、东亚小花蝽(Orius sauteri)、南方小花蝽(Orius strigicollis)、智利小植绥螨(Phytoseiulus persimilis)、泛束盲蝽(Pilophorus typicus)、オオメカメムシ(Piocoris varius)等天敌生物,反式-8-反式-10-十二碳二烯-1-醇(codlelure)、诱蝇酮(cuelure)、香叶醇(geraniol)、舞毒蛾醇(gyptol)、リブルア(liblure)、粉纹夜蛾性诱剂(looplure)、甲基丁香酚(methyl eugenol)、オリフルア(orfralure)、ピーチフルア(peachflure)、フィシルア(phycilure)、14-甲基-1-十八碳烯(pyrimalure)、松节油(turpentine)等信息素并用。
[实施例]
以下通过实施例、制剂例和试验例对本发明进行更具体的说明,但是本发明的范围不被这些实施例、制剂例和试验例所限定。
参考例1(对应于方案1的化合物[4]的化合物的制备)
3-甲氧基乙二酰基氨基-N-(2-乙基-4-七氟异丙基-6-甲基)苯基苯甲酰胺的合成
将3-氨基-N-(2-乙基-4-七氟异丙基-6-甲基)苯基苯甲酰胺8.45g溶解在四氢呋喃80ml中,加入三乙胺3.4ml、4-二甲基氨基吡啶0.3g,在冰冷却下,10℃以下,滴加将甲氧基草酰氯2.45g用四氢呋喃10ml稀释而成的稀释液。然后,将反应液倒入稀盐酸中,将析出的结晶过滤、水洗、干燥得到粗产物。进一步用己烷和乙醇的混合溶剂(5:1)洗涤,得到本发明的化合物的中间体8.53g。熔点为160~163℃
实施例1(对应于方案1的化合物[1]的化合物的制备)
3-(N,N-二甲基氨基乙二酰基氨基)-N-(2-乙基-4-七氟异丙基-6-甲基) 苯基苯甲酰胺(化合物No.1-37)的合成
将3-甲氧基乙二酰基氨基-N-(2-乙基-4-七氟异丙基-6-甲基)苯基苯甲酰胺0.76g和二甲基胺盐酸盐0.25g悬浮在甲醇7ml中,滴加28%甲醇钠甲醇溶液,室温下搅拌整夜,向反应液中加入水,将析出的沉淀过滤、水洗、干燥得到表1记载的化合物(No.1-37)0.78g(无定形)。
实施例2(方案1)
3-(N-环丙基氨基乙二酰基氨基)-N-(2,6-二甲基-4-七氟异丙基)苯基苯甲酰胺(化合物No.1-6)的合成
将3-甲氧基乙二酰基氨基-N-(2,6-二甲基-4-七氟异丙基-)苯基苯甲酰胺0.99g悬浮在甲醇6ml中,滴加将环丙基胺0.25g用甲醇2ml稀释而成的稀释液,室温下搅拌整夜,向反应液中加入水,将析出的沉淀过滤、水洗、干燥得到表1记载的化合物(No.1-6)1.01g。熔点204~206℃
实施例3(方案2)
3-(N,N-二乙基氨基乙二酰基氨基)-N-(2-乙基-4-七氟异丙基-6-甲基)苯基苯甲酰胺(化合物No.1-49)的合成
使3-氨基-N-(2-乙基-4-七氟异丙基-6-甲基)苯基苯甲酰胺0.63g、N,N-二乙基氨基草氨酸0.22g和2-氯-1-甲基吡啶碘化物0.38g悬浮在四氢呋喃7ml中,加入三乙胺0.63ml加热回流2小时后,向反应液中加入水,用乙酸乙酯萃取,水洗、用氯化钠水溶液洗涤后,用硫酸镁干燥后,减压下用蒸发器蒸馏除去溶剂,得到表1记载的化合物(No.1-49)0.81g(无定形)。
实施例4(方案1)
3-(N-乙基氨基乙二酰基氨基)-N-(2-乙基-4-七氟异丙基-6-甲基)苯基苯甲酰胺(化合物No.1-35)的合成
使3-甲氧基乙二酰基氨基-N-(2-乙基-4-七氟异丙基-6-甲基)苯基苯甲酰胺0.76g悬浮在甲醇7ml中,滴加乙胺70%水溶液0.16g,在室温下搅拌整夜,向反应液中加入水,将析出的沉淀过滤、水洗、干燥,得到表1记载的化合物(No.1-35)0.78g。熔点220~222℃
实施例5(方案3)
3-(N-甲基-N-环己基氨基乙二酰基氨基)-N-(2-乙基-4-七氟异丙基-6-甲基)苯基苯甲酰胺(化合物No.1-48)的合成
使3-氨基-N-(2-乙基-4-七氟异丙基-6-甲基)苯基苯甲酰胺0.63g和吡啶0.24g悬浮在四氢呋喃7ml中,冰冷却下滴加将N-甲基-N-环己基氨基草酰氯0.35g用四氢呋喃2ml稀释而成稀释液,然后在室温下搅拌整夜,向反应液中加入稀盐酸,用乙酸乙酯萃取,水洗、用氯化钠水溶液洗涤后,用硫酸镁干燥后,减压下用蒸发器蒸馏除去溶剂,得到表1记载的化合物(No.1-48)0.87g(无定形)。
实施例6(方案1)
3-(吡咯烷-1-基乙二酰基氨基)-N-(2,6-二甲基-4-七氟异丙基-)苯基苯甲酰胺(化合物No.1-33)的合成
使3-甲氧基乙二酰基氨基-N-(2,6-二甲基-4-七氟异丙基)苯基苯甲酰胺0.99g悬浮在甲醇8ml中,滴加吡咯烷0.21g,在室温下搅拌整夜,向反应液中加入水,将析出的沉淀过滤、水洗、干燥,得到表1记载的化合物(No.1-33)1.04g(无定形)。
实施例7
3-(N-(叔丁基)-N-甲基氨基乙二酰基氨基)-N-(2-氯-4-七氟异丙基-6-甲基)苯基苯甲酰胺(化合物No.1-61)的合成
实施例7-(1)
N-(叔丁基)-N-甲基-乙氧基乙二酰胺的合成
用叔丁基甲基醚200ml稀释叔丁基甲基胺15.08g,加入三乙胺27.4ml,在冰冷却下滴加将乙基乙二酰氯24.85g用叔丁基甲基醚40ml稀释而成的稀释液,滴加结束后向反应液中加入稀盐酸进行分液,有机层用碳酸氢钠水、饱和食盐水洗涤后,用硫酸镁干燥,蒸馏除去叔丁基甲基醚,得到目的化合物N-(叔丁基)-N-甲基-乙氧基乙二酰胺30.25g(收率93.4%,油状)。
实施例7-(2)
N-(叔丁基)-N-甲基氨基草氨酸的合成
使N-(叔丁基)-N-甲基-乙氧基乙二酰胺20.0g悬浮在甲醇30ml、水50ml中,冰冷却下,滴加50%氢氧化钠水溶液9.42g,搅拌1小时。加入浓盐酸成为酸性,加入叔丁基甲基醚进行分液,将有机层水洗,用硫酸镁干燥后,蒸馏除去叔丁基甲基醚,得到目的化合物N-(叔丁基)-N-甲基氨基草氨酸12.37g(收率73%,固体)。
实施例7-(3)(方案2)
3-(N-(叔丁基)-N-甲基氨基乙二酰基氨基)-N-(2-氯-4-七氟异丙基-6-甲基)苯基苯甲酰胺(化合物No.1-61)的合成
使3-氨基-N-(2-氯-4-七氟异丙基-6-甲基)苯基苯甲酰胺0.43g、N-(叔丁基)-N-甲基草氨酸0.18g和2-氯-1-甲基吡啶碘化物0.28g悬浮在四氢呋喃6ml中,加入三乙胺0.46ml,室温下搅拌整夜后,从反应液减压下蒸馏除去溶剂等后,残渣用硅胶柱色谱(己烷:乙酸乙酯=1.5:1)纯化,得到表1记载的化合物(No.1-61)0.53g(无定形)。
实施例8
3-(N-(2-氟乙基)-N-甲基氨基乙二酰基氨基)-N-(2-乙基-4-七氟异丙基-6-甲基)苯基苯甲酰胺(化合物No.1-103)的合成
实施例8-(1)
N-(2-氟乙基)-甲氧基乙二酰胺的合成
将草酸二甲酯14.17g和2-氟乙胺盐酸盐10.00g溶解在甲醇130ml中,冰冷却下加入用甲醇30ml稀释28%甲醇钠的甲醇溶液19.30g而成的稀释液。滴加结束后使反应液为室温,过滤反应液中析出的结晶。减压下浓缩滤液,向残渣中加入二乙醚,再次过滤析出的结晶,从滤液蒸馏除去二乙醚,得到目的化合物N-(2-氟乙基)-甲氧基乙二酰胺10.63g(收率79.3%,油状物)。
实施例8-(2)
N-(2-氟乙基)-N-甲基-甲氧基乙二酰胺的合成
向N-(2-氟乙基)-甲氧基乙二酰胺3.00g中加入N,N-二甲基甲酰胺25ml、二甲氧基乙烷5ml和碘甲烷4ml。冰冷却下,添加氢化钠(油中60%)0.96g。使反应液为室温,加入稀盐酸和乙酸乙酯进行分液,将有机层水洗,用硫酸镁干燥后,蒸馏除去乙酸乙酯,得到的粗产物用己烷洗涤,得到目的化合物N-(2-氟乙基)-N-甲基-甲氧基乙二酰胺1.66g(收率50.9%,油状物)。
实施例8-(3)
N-(2-氟乙基)-N-甲基草氨酸的合成
使N-(2-氟乙基)-N-甲基-甲氧基乙二酰胺1.56g悬浮在甲醇6ml、水5ml中,冰冷却下滴加15%氢氧化钠水溶液3.2g,搅拌1小时,加入浓盐酸,加入乙酸乙酯进行分液,将有机层水洗,用硫酸镁干燥后,蒸馏除去乙酸乙酯,得到目的化合物N-(2-氟乙基)-N-甲基氨基草氨酸0.94g(收率66%,固体)。
实施例8-(4)(方案2)
3-(N-(2-氟乙基)-N-甲基氨基乙二酰基氨基)-N-(2-乙基-4-七氟异丙基-6-甲基)苯基苯甲酰胺(化合物No.1-103)的合成
使3-氨基-N-(2-乙基-4-七氟异丙基-6-甲基)苯基苯甲酰胺0.42g、N-(2-氟乙基)-N-甲基草氨酸0.18g和2-氯-1-甲基吡啶碘化物0.31g悬浮在四氢呋喃7ml中,加入三乙胺0.51ml,在室温下搅拌5小时后,从反应液蒸馏除去溶剂等后,残渣用硅胶柱色谱(己烷:乙酸乙酯=1:1)纯化,得到表1记载的化合物(No.1-103)0.47g(无定形)。
实施例9
3-(N-(2,2,2-三氟乙基)-N-甲基氨基乙二酰基氨基)-N-(2-溴-4-七氟异丙基-6-甲基)苯基苯甲酰胺(化合物No.1-90)的合成
实施例9-(1)
N-(2,2,2-三氟乙基)-乙氧基乙二酰胺的合成
用叔丁基甲基醚150ml稀释2,2,2-三氟乙胺25g,加入水200ml和碳酸氢钠33.6g,在冰冷却下搅拌的同时,用叔丁基甲基醚40ml稀释乙基乙二酰氯24.85g并滴加。滴加结束后将反应液分液,有机层用稀盐酸水、饱和食盐水洗涤后,用硫酸镁干燥,蒸馏除去叔丁基甲基醚,得到目的化合物N-(2,2,2-三氟乙基)-乙氧基乙二酰胺40.28g(收率80%,结晶)。
实施例9-(2)
N-(2,2,2-三氟乙基)-N-甲基-乙氧基乙二酰胺的合成
将60%氢化钠4.48g用己烷洗涤,悬浮在N,N-二甲基甲酰胺80ml中,冰冷却下,添加N-(2,2,2-三氟乙基)-乙氧基乙二酰胺20.26g。发泡结束后,用N,N-二甲基甲酰胺20ml稀释碘甲烷17.0g并加入。50℃下搅拌约2小时,向反应液中加入稀盐酸、叔丁基甲基醚,进行分液,有机层用水、饱和食盐水洗涤,用硫酸镁干燥后,蒸馏除去叔丁基甲基醚,得到目的化合物N-(2,2,2-三氟乙基)-N-甲基-乙氧基乙二酰胺16.9g(收率78%,油状物)。
实施例9-(3)
N-(2,2,2-三氟乙基)-N-甲基氨基草氨酸的合成
使N-(2,2,2-三氟乙基)-N-甲基-乙氧基乙二酰胺16.92g悬浮在甲醇20ml和水30ml中,冰冷却下,滴加50%氢氧化钠水溶液7.00g,搅拌1小时。加入浓盐酸使反应液为酸性,加入叔丁基甲基醚进行分液,将有机层水洗,用硫酸镁干燥后,蒸馏除去叔丁基甲基醚,得到目的化合物N-(2,2,2-三氟乙基)-N-甲基氨基草氨酸11.16g(收率80%,固体)。
实施例9-(4)(方案2)
3-(N-(2,2,2-三氟乙基)-N-甲基氨基乙二酰基氨基)-N-(2-溴-4-七氟异丙基-6-甲基)苯基苯甲酰胺(化合物No.1-90)的合成
使3-氨基-N-(2-溴-4-七氟异丙基-6-甲基)苯基苯甲酰胺0.57g、N-(2,2,2-三氟乙基)-N-甲基草氨酸0.26g和2-氯-1-甲基吡啶碘化物0.34g悬浮在四氢呋喃6ml中,加入三乙胺0.55ml,在室温下搅拌整夜后,减压下从反应液蒸馏除去溶剂等后,残渣用硅胶柱色谱(己烷:乙酸乙酯=2:1)纯化,得到表1记载的化合物(No.1-90)0.61g(无定形)。
实施例10
与实施例1~9同样地制备本发明的化合物。以下表1中记载通过实施例制备的本发明的化合物的代表性的化合物,但是本发明不限于它们。
而且,表中,Me表示甲基,Et表示乙基,Pr表示丙基,Bul表示丁基,“n-”表示正,“t-”表示叔,“s-”表示仲,“i-”表示异,“c-”表示环。
表1
表2
表3
化合物No. | R1 | R2 | R3 | R4 | R6 | R7 | Yn | 熔点(℃) |
3-1 | Me | Et | Me | t-Bu | Me | H | H | 无定形 |
3-2 | Me | Et | Me | CH2CF3 | Me | H | H | 无定形 |
3-3 | Me | Et | Me | CH2CF3 | H | Me | H | 无定形 |
3-4 | Me | Et | Me | Et | H | H | 6-F | 无定形 |
3-5 | Me | Et | Me | CH2CF3 | H | H | 6-F | 无定形 |
下表4示出由表1~表3记载的化合物中物性为无定形的化合物的1H-NMR得到的物性值。
表4
接着对制剂例进行说明。而且,份表示质量份。
制剂例1 乳剂
将本发明的化合物(10份)、二甲苯(60份)、N-甲基-2-吡咯烷酮(20份)和ソルポール3005X(非离子型表面活性剂与阴离子型表面活性剂的混合物、东邦化学工业株式会社、商品名)(10份)均一地混合溶解,得到乳剂。
制剂例2 可湿性粉剂-1
将本发明的化合物(20份)、ニップシールNS-K(白炭黑、东ソー·シリカ株式会社、商品名)(20份)、カオリンクレー(高岭土、竹原化学工业株式会社、商品名)(20份)、サンエキスP-252(木质素磺酸钠、日本制纸ケミカル株式会社、商品名)(5份)和ルノックスP-65L(烷基烯丙基磺酸盐、东邦化学工业株式会社、商品名)(5份)用气流磨均一地混合粉碎,得到可湿性粉剂。
制剂例3 可湿性粉剂-2
将本发明的化合物(20份)、ニップシールNS-K(20份)、カオリンクレー(50份)、ルノックス1000C(萘磺酸盐缩合物、东邦化学工业株式会社、商品名)(5份)和ソルポール5276(非离子型表面活性剂、东邦化学工业株式会社、商品名)(5份)用气流磨均一地混合粉碎,得到可湿性粉剂。
制剂例4 溶胶剂(易流动剂)-1
使本发明的化合物(20份)分散在预先混合的丙二醇(5份)、ソルポール7933(阴离子型表面活性剂、东邦化学工业株式会社、商品名)(5份)、水(50份)中,形成浆状混合物,接着将该浆状混合物用戴诺磨(シンマルエンタープライゼス社)湿式粉碎后,添加预先将黄原胶(0.2份)良好地混合分散在水(19.8份)中而成的分散液,得到溶胶剂(易流动剂)。
制剂例5溶胶剂(易流动剂)-2
将本发明的化合物(20份)、ニューカルゲンFS-26(二辛基磺基琥珀酸酯与聚氧乙烯三苯乙烯基苯基醚的混合物、竹本油脂株式会社、商品名)(5份)、丙二醇(8份)、水(50份)预先混合,将该浆状混合物用戴诺磨(シンマルエンタープライゼス社)湿式粉碎。接着使黄原胶(0.2份)良好地混合分散在水(16.8份)中,制成凝胶状物,与进行了粉碎的浆充分混合,得到溶胶剂(易流动剂)。
接着,举出具体的实施例对本发明的化合物的作用效果和有用性进行说明。
试验例1:对小菜蛾幼虫的杀虫效果
将白菜的种子播种到苗钵(jiffy pot)后育苗3周。对该钵种植的植物的叶部,将按照制剂例1制备的乳剂的水稀释液使用喷枪充分撕布到茎叶部(1浓度、1反复)。将药液风干后,保持在25℃的恒温室内,放虫5天后调查幼虫的生死以及痛苦,将痛苦虫作为死亡来求得杀虫率(%)。而且,作为比较化合物,使用日本特开2006-306771号公报(专利文献25)记载的化合物A和B。
上述试验的结果,本发明的化合物No.1-1、1-3~7、1-9~19、1-21~57、1-59~60、1-62、1-64~67、1-69~71、1-73~78、1-80、1-83~105、1-109、1-111~116、2-1~3、2-13~18、3-4~5的化合物在500ppm的浓度下表现出100%的杀虫率。另一方面,比较化合物A和B都未表现出杀虫活性。
此外,进行低浓度试验,结果本发明的化合物No.1-4~7、1-9~13、1-19、1-21~28、1-30、1-32~33、1-35~45、1-47、1-49~51、1-53、1-56~57、1-59~60、1-62、1-64~67、1-69~71、1-73~78、1-83、1-85~97、1-99~105、1-109、1-112、1-114~116、2-1~3、2-13~18、3-4~5的化合物在50ppm的浓度下表现出100%的杀虫率。
此外,在12.5ppm或5ppm下进行低浓度试验,结果本发明的化合物No.1-45、1-62、1-64~65、1-69~71、1-88~94、1-96、1-99~101、1-103~105、1-109、1-112、1-114~116、2-3、2-13~18、3-4的化合物在12.5ppm的浓度下表现出100%的杀虫率。本发明的化合物No.1-22~25、1-28、1-37~38、1-44、1-57、1-59~60、1-75、1-86~87的化合物在5ppm的浓度下表现出100%的杀虫率。
试验例2:对二斑叶螨的杀成虫试验
在加入有水的430ml容量的聚乙烯杯上盖上中央开孔(直径约5mm)的盖。在直径6.5cm的圆形滤纸上形成宽度5mm左右的切口,从盖的孔插入向下方垂下的长方形的部分以浸渍在杯内的水中,在该滤纸上载置脱脂棉。如此,在不断补给杯内的水的状态的脱脂棉上载置2块由菜豆初生叶制成的叶盘(leaf disk)(2cm×5cm),在该叶盘上接种二斑叶螨雌成虫10只。将该杯置于高50cm、10cm直径的丙烯酸制圆筒内,使用喷枪以每1杯1.35ml撕布(1浓度、1反复)按照制剂例1制备的乳剂的水稀释液。撕布后保持在25℃的恒温室内。处理4天后在双目镜下调查成虫的生死以及痛苦,将痛苦虫作为死亡来求得杀螨率(%)。而且,作为比较化合物,使用日本特开2006-306771号公报记载的化合物A和B。
上述试验的结果,本发明的化合物No. 1-21~23、1-26~28、1-37~47、1-49~50、1-56~57、1-59~60、1-64~65、1-69~71、1-74、1-78、1-86~97、1-100~101、1-103~105、1-109、1-112,1-114~116、2-1~3、2-13~18的化合物在50ppm的浓度下表现出100%的杀成虫率。另一方面,比较化合物A和B都未表现出杀虫活性。
此外,在12.5ppm或5ppm下进行低浓度试验,结果本发明的化合物No. 1-46、1-50、1-64~65、1-69~71、1-88~94、1-96、1-100、1-103、1-109、1-115~116、2-1~3、2-13~18的化合物在12.5ppm的浓度下表现出100%的杀成虫率。本发明的化合物No. 1-28、1-40、1-44、1-86~87的化合物在5ppm的浓度下表现出100%的杀成虫率。
试验例3:对桃蚜幼虫的杀虫效果
在切成3cm×4cm的白菜叶片上接种3只桃蚜成虫,在25℃的恒温室内让其产仔48小时。除去成虫后,将叶片在按照制剂例1制备的乳剂的水稀释液中进行5秒钟浸渍处理,保持在25℃的恒温室内。处理后第7天调查若虫的生死以及痛苦,将痛苦虫作为死亡来求得杀虫率(%)。而且,作为比较化合物,使用日本特开2006-306771号公报记载的化合物A和B。
上述试验的结果,本发明的化合物No. 1-21、1-24、1-28、1-33、1-37~42、1-44、1-47、1-56~57、1-64~65、1-69~71、1-87、1-89~96、1-103~104、1-109、1-115~116、2-2~3、2~13~18的化合物在50ppm的浓度下表现出100%的杀虫率。另一方面,比较化合物A和B都未表现出杀虫活性。
此外,在12.5ppm或5ppm下进行低浓度试验,结果本发明的化合物No. 1-65、1-69~71、1-89~94、1-97、1-103~104、1-109、1-115、2-2、2-15、1-17~18的化合物在12.5ppm的浓度下表现出100%的杀虫率。本发明的化合物No. 1-38~39、1-87的化合物在5ppm的浓度下表现出100%的杀虫率。
Claims (8)
1.3-氨基乙二酰基氨基苯甲酰胺衍生物,其特征在于,以下式[1]表示,
式中,R1和R2分别独立地表示氢原子、C1~C3烷氧基、C1~C3卤代烷氧基、卤原子或C1~C5烷基,
R3和R4分别独立地表示氢原子、C1~C8烷基、C1~C8卤代烷基、烯丙基、C3~C8环烷基或C3~C6环烷基C1~C4烷基,或者R3和R4可以相互键合形成C3~C8亚烷基键,
R5表示C1~C5卤代烷基,
R6和R7分别独立地表示氢原子,
Y分别独立地表示氢原子、卤原子、羟基、硝基、氰基、C1~C5烷基、C1~C5卤代烷基、C1~C3烷基氨基、二C1~C3烷基氨基、C1~C3烷氧基或C1~C3卤代烷氧基,
Z分别独立地表示氢原子、卤原子、羟基、硝基、氰基、C1~C5烷基、C1~C5卤代烷基、C1~C3烷氧基或C1~C3卤代烷氧基,
n表示0~4的整数,m表示0~2的整数。
2.如权利要求1所述的3-氨基乙二酰基氨基苯甲酰胺衍生物,其中,上式[1]中,
R1和R2分别独立地表示C1~C3烷氧基、C1~C3卤代烷氧基、卤原子或C1~C5烷基,
R3和R4分别独立地表示氢原子、C1~C6烷基、C1~C6卤代烷基、烯丙基、C3~C6环烷基或C3~C6环烷基C1~C4烷基,或者R3和R4可以相互键合形成C3~C6亚烷基键,
R5表示C1~C5卤代烷基,
R6和R7分别独立地表示氢原子,
Y分别独立地表示氢原子、卤原子、氰基、C1~C3烷基或C1~C3卤代烷基,
Z分别独立地表示氢原子、卤原子或C1~C3烷基,
n表示0~4的整数,m表示0~2的整数。
3.如权利要求2所述的3-氨基乙二酰基氨基苯甲酰胺衍生物,其中,上式[1]中,R1为甲氧基、三氟甲氧基、甲基、乙基或异丙基,R2为氯原子、溴原子、碘原子、甲基或乙基。
4.如权利要求2所述的3-氨基乙二酰基氨基苯甲酰胺衍生物,其中,上式[1]中,R3为甲基或乙基,R4为C1~C6烷基、C1~C6卤代烷基、烯丙基、C3~C6环烷基或C3~C6环烷基C1~C4烷基,或者R3和R4可以相互键合形成C3~C6亚烷基键。
5.制备权利要求1所述化合物的方法,其中,使式[4]所示的化合物与式[5]所示的化合物反应,
式[4]中,R8为碳原子数1~5的烷基,
R1和R2分别独立地表示氢原子、C1~C3烷氧基、C1~C3卤代烷氧基、卤原子或C1~C5烷基,
R5表示C1~C5卤代烷基,
R6和R7分别独立地表示氢原子,
Y分别独立地表示氢原子、卤原子、羟基、硝基、氰基、C1~C5烷基、C1~C5卤代烷基、C1~C3烷基氨基、二C1~C3烷基氨基、C1~C3烷氧基或C1~C3卤代烷氧基,
Z分别独立地表示氢原子、卤原子、羟基、硝基、氰基、C1~C5烷基、C1~C5卤代烷基、C1~C3烷氧基或C1~C3卤代烷氧基,
n表示0~4的整数,m表示0~2的整数,
式[5]中,R3和R4分别独立地表示氢原子、C1~C8烷基、C1~C8卤代烷基、烯丙基、C3~C8环烷基或C3~C6环烷基C1~C4烷基,或者R3和R4可以相互键合形成C3~C8亚烷基键。
6.制备权利要求1所述化合物的方法,其中,使式[3]所示的化合物与式[6]所示的化合物反应,
式[3]中,
R1和R2分别独立地表示氢原子、C1~C3烷氧基、C1~C3卤代烷氧基、卤原子或C1~C5烷基,
R5表示C1~C5卤代烷基,
R6和R7分别独立地表示氢原子,
Y分别独立地表示氢原子、卤原子、羟基、硝基、氰基、C1~C5烷基、C1~C5卤代烷基、C1~C3烷基氨基、二C1~C3烷基氨基、C1~C3烷氧基或C1~C3卤代烷氧基,
Z分别独立地表示氢原子、卤原子、羟基、硝基、氰基、C1~C5烷基、C1~C5卤代烷基、C1~C3烷氧基或C1~C3卤代烷氧基,
n表示0~4的整数,m表示0~2的整数,
式[6]中,R3和R4分别独立地表示氢原子、C1~C8烷基、C1~C8卤代烷基、烯丙基、C3~C8环烷基或C3~C6环烷基C1~C4烷基,或者R3和R4可以相互键合形成C3~C8亚烷基键。
7.制备权利要求1所述化合物的方法,其中,使式[3]所示的化合物与式[7]所示的化合物反应,
式[3]中,
R1和R2分别独立地表示氢原子、C1~C3烷氧基、C1~C3卤代烷氧基、卤原子或C1~C5烷基,
R5表示C1~C5卤代烷基,
R6和R7分别独立地表示氢原子,
Y分别独立地表示氢原子、卤原子、羟基、硝基、氰基、C1~C5烷基、C1~C5卤代烷基、C1~C3烷基氨基、二C1~C3烷基氨基、C1~C3烷氧基或C1~C3卤代烷氧基,
Z分别独立地表示氢原子、卤原子、羟基、硝基、氰基、C1~C5烷基、C1~C5卤代烷基、C1~C3烷氧基或C1~C3卤代烷氧基,
n表示0~4的整数,m表示0~2的整数,
式[7]中,R3和R4分别独立地表示氢原子、C1~C8烷基、C1~C8卤代烷基、烯丙基、C3~C8环烷基或C3~C6环烷基C1~C4烷基,或者R3和R4可以相互键合形成C3~C8亚烷基键,X为卤原子。
8.杀虫、杀螨剂,其特征在于,含有权利要求1~4中任意一项所述的3-氨基乙二酰基氨基苯甲酰胺衍生物作为有效成分。
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