CN106749129A - 杀虫化合物 - Google Patents

杀虫化合物 Download PDF

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Publication number
CN106749129A
CN106749129A CN201710079573.1A CN201710079573A CN106749129A CN 106749129 A CN106749129 A CN 106749129A CN 201710079573 A CN201710079573 A CN 201710079573A CN 106749129 A CN106749129 A CN 106749129A
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CN
China
Prior art keywords
phenyl
compound
alkyl
formula
methyl
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Pending
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CN201710079573.1A
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English (en)
Inventor
P·梅恩菲什
C·R·A·古德弗雷
P·J·M·容
O·F·休特
P·雷诺
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Syngenta Participations AG
Syngenta Crop Protection LLC
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Syngenta Participations AG
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Priority claimed from GB0907824A external-priority patent/GB0907824D0/en
Application filed by Syngenta Participations AG filed Critical Syngenta Participations AG
Publication of CN106749129A publication Critical patent/CN106749129A/zh
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • 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
    • C07C237/44—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 carbon atoms of carboxamide groups, amino groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • 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
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
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    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
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    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract

本发明涉及式(I)的双酰胺衍生物，制备它们的方法和中间体，还涉及利用它们防除害虫如昆虫、蜱螨、线虫和软体动物害虫的方法以及包含这些衍生物的杀昆虫的、杀螨的、杀线虫的和杀软体动物的组合物。

Description

杀虫化合物
本申请是母案为中国发明专利申请201080019742.9的分案申请。
本发明涉及双酰胺衍生物，制备它们的方法和中间体，还涉及利用它们除害虫如昆虫、蜱螨、线虫和软体动物害虫的方法以及包含这些衍生物的杀昆虫的、杀螨的、杀线虫的和杀软体动物的组合物。
具有杀虫性质的化合物还揭示于EP 1,714,958,JP 2006/306771,WO 2006/137376,EP 1,916,236,WO 2007/017075,WO 2008/000438,WO 2008/074427和WO 2009/049845中。但还缺乏防除害虫的替代方法。优选地，新型化合物可能具有更高的杀虫特性，如更高的杀虫功效，更高的选择性，更低的毒性和倾向性，以产生针对更广泛害虫的抗性或活性。这些化合物可更方便地制得且在施用点的施用和保留更为有效，或者说更容易生物降解。
现令人惊奇地发现被芳基全氟丁基取代的特定双酰胺衍生物具有非常有益的特性，因此特别适合用作杀虫剂。
本发明因此提供式(I)化合物:
其中
Q1是芳基或杂杂环基，其每个可选地由1-5个相同或相异的R3取代基取代；
Q2选自：
2-乙基-6-甲基-4-(九氟丁-2-基)苯基,
2-溴-6-氯-4-(九氟丁-2-基)苯基,
2,6-二氯-4-(九氟-丁-2-基)苯基,
2,6-二甲基-4-(九氟-丁-2-基)苯基,
2-氯-6-甲氧基甲基-4-(九氟丁-2-基)苯基,和
2溴-6-甲氧基甲基-4-(九氟丁-2-基)苯基；
R1选自氢，C1-C8烷基，C1-C8烷基羰基，C1-C8烷氧基羰基及C1-C4烷基-C(O)NH2；
R2选自氢，C1-C8烷基，C1-C8烷基羰基，C1-C8烷氧基羰基及C1-C4烷基-C(O)NH2；和
R3选自氰基，硝基，卤素，羟基，乙酸基，C1-C4烷基，C1-C4卤代烷基，C1-C4氧烷基，C1-C4卤代氧烷基，C1-C4烷硫基，C1-C4氧烷基-C1-C4烷基，C1-C4氧烷基-C1-C4氧烷基，CN-C1-C4烷基，C1-C4烷基-C(O)O，C1-C4烷基-S(O)2,NH2，C1-C4烷基NH，(C1-C4烷基)2N，(C1-C4烷基O)2P(O)O，苯基以及含有1-3个独立选自氮，氧和硫的5-6元单环杂环基；
或农业化学可接受的盐或其N-氧化物。
式(I)化合物可以不同几何或光学异构体(对映异构体和/或非对映异构体)或互变异构体的形式存在。本发明涵盖所有这样的异构体和互变异构体及其以全部比例的混合物，以及如氘化化合物的同位素形式。
除非另有说明，烷基，无论作为其本身或是作为如烷氧基，烷基羰基或烷氧基羰基等其它基团中的一部分，它既可以是直链也可以是支链并且优选地包含1-6碳原子，更优选为1-4个，最优选为1-3个。烷基的实例包括甲基，乙基，正丙基，异丙基，正丁基，仲丁基，异丁基和叔丁基。
卤素是指氟、氯、溴或碘。
卤代烷基基团可含有一个多或多个相同或不同的卤素原子，且包括如三氟甲基，氯二氟甲基，2,2,2-三氟乙基或2,2二氟乙基。全氟烷基基团是用氟原子完全取代的烷基基团且包括如三氟甲基，五氟乙基，七氟丙-2-基和九氟-丁-2-基。
芳基包括苯基，萘基，蒽基，茚基，菲基和联苯基，优选为苯基。
杂芳基是指含3-14个，优选4-10个，更有选4-7个，最优选5-6个环原子且包括1-6个，优选1-4个，更有选1,2或3个独立选自氮，氧和硫的杂原子的单-，双-或三环芳香烃。实例包括呋喃基，噻吩基，吡咯基，咪唑基，吡唑基，噻唑基，异噻唑基，恶唑基，异恶唑基，恶二唑基，噻二唑基，三唑基，四唑基，吡啶基，哒嗪基，嘧啶碱基，吡嗪基，三嗪基，四唑基，吲哚基，苯并噻吩基，苯并呋喃基，苯并咪唑基，苯并噻二唑基，吲唑基，苯并三唑基，苯并噻唑基，苯并恶唑基，喹啉基，异喹啉基，酞嗪基，喹喔啉基，间二氮杂萘基，噌嗪基和萘啶基。优选为包括1,2或3个独立选自氮，氧和硫的杂原子的含4-7个，优选地5-6个环原子的单环杂芳基基团。
如这里所说的杂环基包括杂芳基，另外也可以是饱和或部分不饱和的、包括含有1-6个，优选1-4个，更有选1,2或3个独立选自氮、氧和硫的杂原子的3-10个环原子。非芳族杂环基基团的实例为环氧乙烷基，氮杂环丁烷基，四氢呋喃基，硫羟烷基，吡咯烷基，吡咯啉基，咪唑烷基，咪唑啉基，噻吩烷基，二氧杂环烷基，二氢吡喃基，四氢吡喃基，呱啶基，吡唑啉基，吡唑烷基，1,3二氧杂环己基，1,4二氧杂环己基，吗啉基，二噻烷基，硫代吗啉基，哌嗪基，吖庚因基，恶吖庚因基，噻吖庚因基，噻唑啉基，二氮杂环庚烷基，2,3-二氢苯并呋喃基，3,4-二氢-2H-苯并[b][1,4]二恶烷乙恶二酮，苯并[1,3]二氧杂环烷基以及2,3二氢苯并[1,4]特戊酰基。
Q1,Q2,R1,R2和R3在任何组合中的优选值如下所述。
优选地，Q1为芳基或杂芳基；每个可选地被1-5个相同或不同的R3取代基取代。
更优选地，Q1选自苯基，联苯基和一个包含1,2或3个独立选自氮，氧和硫的杂原子的5-6元单环杂芳基基团；其每个可选地被1-5个相同或不同的R3取代基取代。
还更优选地，Q1选自苯基，联苯基，呋喃基，噻吩基，吡咯基，咪唑基，吡唑基，噻唑基，异噻唑基，恶唑基，异恶唑基，恶二唑基，噻二唑基，三唑基，四唑基，吡啶基，哒嗪基，嘧啶碱基，吡嗪基，三嗪基，四唑基，吲哚基，苯并噻吩基，苯并呋喃基，苯并咪唑基，苯并噻二唑基，吲唑基，苯并三唑基，苯并噻唑基，苯并恶唑基，喹啉基，异喹啉基，酞嗪基，喹喔啉基，间二氮杂萘基，噌嗪基和萘啶基。每个可选地被1-5个R3，更优选地被1-3个相同或不同的R3取代基取代。
更为优选地，Q1选自苯基，联苯基，呋喃基，吡啶基，噻吩基，噻二唑基，恶唑基，异恶唑基，噻唑基，异噻唑基，吡唑基和嘧啶碱基；每个可选地被1-3个相同或不同的R3取代基取代。
优选地，R3选自氰基，硝基，氟，氯，溴，碘，羟基，乙酸基，C1-C4烷基，C1-C4卤代烷基，C1-C4氧烷基，C1-C4卤代氧烷基，C1-C4烷硫基，C1-C4氧烷基-C1-C4烷基，C1-C4氧烷基-C1-C4氧烷基，CH2-CN，C(O)OCH3，S(O)2CH3，NH2，N(CH3)2，OP(O)(CH2CH3)2，苯基，N-吡咯基，噻二唑基和吡啶基。
更优选地，R3选自氰基，硝基，氟，氯，溴，碘，羟基，乙酸基，甲基，乙基，异丙基，叔丁基，二氟甲基，三氟甲基，甲氧基，乙氧基，二氟甲氧基，三氟甲氧基，甲硫基，异丙硫基，3-乙氧基-正-丙基，甲氧基甲基，2-甲氧基乙氧基，CH2CN，C(O)OCH3，S(O)2CH3，NH2，N(CH3)2，OP(O)(CH2CH3)2，苯基，N-吡咯基，噻二唑基和吡啶基。
最优选地，R3选自氰基，硝基，溴，氯，氟，甲基，乙基，三氟甲基，甲氧基和三氟甲氧基。
Q1最优选为如此处所述实例和表A-M中的化合物。
优选地，Q2选自
2乙基-6-甲基-4-(九氟-丁-2-基)苯基，
2-溴-6-氯-4-(九氟-丁-2-基)苯基，及
2,6-二氯-4-(九氟-丁-2-基)苯基。
优选地，R1选自氢。优选地，R2选自氢
在第一个优选方面，本发明提供一种式(I)的化合物，其中Q2为2-乙基-6-甲基-4-(九氟-丁-2-基)苯基；且Q1，R1，R2和R3如此处所定义。
在第一个优选方面的一个优选实施例中，本发明提供一种式(I)的化合物，其中
Q2是2-乙基-6-甲基-4-(九氟-丁-2-基)苯基；
Q1选自苯基，联苯基，呋喃基，噻吩基，吡咯基，咪唑基，吡唑基，噻唑基，异噻唑基，恶唑基，异恶唑基，恶二唑基，噻二唑基，三唑基，四唑基，吡啶基，哒嗪基，嘧啶碱基，吡嗪基，三嗪基，四唑基，吲哚基，苯并噻吩基，苯并呋喃基，苯并咪唑基，苯并噻二唑基，吲唑基，苯并三唑基，苯并噻唑基，苯并恶唑基，喹啉基，异喹啉基，酞嗪基，喹喔啉基，间二氮杂萘基，噌嗪基和萘啶基。每个可选地被1-3个相同或不同的R3取代基取代。
R1和R2均为氢；和
R3选自氰基，硝基，氟，氯，溴，碘，羟基，乙酸基，甲基，乙基，异丙基，叔丁基，二氟甲基，三氟甲基，甲氧基，乙氧基，二氟甲氧基，三氟甲氧基，甲硫基，异丙硫基，3-乙氧基-正-丙基，甲氧基甲基，2-甲氧基乙氧基，CH2-CN，C(O)OCH3，S(O)2CH3，NH2，N(CH3)2，OP(O)(CH2CH3)2，苯基，N-吡咯基，噻二唑基和吡啶基。
在第一个优选方面的一个更优选实施例中，本发明提供一种式(I)的化合物，其中
Q2是2-乙基-6-甲基-4-(九氟-丁-2-基)苯基；
Q1选自苯基，联苯基，呋喃基，吡啶基，噻吩基，噻二唑基，恶唑基，异恶唑基，噻唑基，异噻唑基，吡唑基和嘧啶碱基；每个可选地被1-3个相同或不同的R3取代基取代。
R1和R2均为氢；和
R3选自氰基，硝基，溴，氯，氟，甲基，乙基，三氟甲基，甲氧基和三氟甲氧基。
在第二个优选方面，本发明提供一种式(I)的化合物，其中Q2是2-溴-6-氯-4-(九氟-丁-2-基)苯基；Q1,R1,R2和R3如此处所定义。
在第二个优选方面的一个优选实施例中，本发明提供一种式(I)的化合物，其中
Q2是2-溴-6-氯-4-(九氟-丁-2-基)苯基；
Q1选自苯基，联苯基，呋喃基，噻吩基，吡咯基，咪唑基，吡唑基，噻唑基，异噻唑基，恶唑基，异恶唑基，恶二唑基，噻二唑基，三唑基，四唑基，吡啶基，哒嗪基，嘧啶碱基，吡嗪基，三嗪基，四唑基，吲哚基，苯并噻吩基，苯并呋喃基，苯并咪唑基，苯并噻二唑基，吲唑基，苯并三唑基，苯并噻唑基，苯并恶唑基，喹啉基，异喹啉基，酞嗪基，喹喔啉基，间二氮杂萘基，噌嗪基和萘啶基。每个可选地被1-3个相同或不同的R3取代基取代。
R1和R2均为氢；和
R3选自氰基，硝基，氟，氯，溴，碘，羟基，乙酸基，甲基，乙基，异丙基，叔丁基，二氟甲基，三氟甲基，甲氧基，乙氧基，二氟甲氧基，三氟甲氧基，甲硫基，异丙硫基，3-乙氧基-正-丙基，甲氧基甲基，2-甲氧基乙氧基，CH2-CN，C(O)OCH3，S(O)2CH3，NH2，N(CH3)2，OP(O)(CH2CH3)2，苯基，N-吡咯基，噻二唑基和吡啶基。
在第二个优选方面的一个更优选实施例中，本发明提供一种式(I)的化合物，其中
Q2是2-溴-6-氯-4-(九氟-丁-2-基)苯基
Q1选自苯基，联苯基，呋喃基，吡啶基，噻吩基，噻二唑基，恶唑基，异恶唑基，噻唑基，异噻唑基，吡唑基和嘧啶碱基；每个可选地被1-3个相同或不同的R3取代基取代。
R1和R2均为氢；和
R3选自氰基，硝基，溴，氯，氟，甲基，乙基，三氟甲基，甲氧基和三氟甲氧基。
在第三个优选方面，本发明提供一种式(I)的化合物，其中Q2是2,6-二氯-4-(九氟-丁-2-基)苯基；Q1,R1,R2和R3如其中所定义。
在第三个优选方面的一个优选实施例中，本发明提供一种式(I)的化合物，其中
Q2是2,6-二氯-4-(九氟-丁-2-基)苯基；
Q1选自苯基，联苯基，呋喃基，噻吩基，吡咯基，咪唑基，吡唑基，噻唑基，异噻唑基，恶唑基，异恶唑基，恶二唑基，噻二唑基，三唑基，四唑基，吡啶基，哒嗪基，嘧啶碱基，吡嗪基，三嗪基，四唑基，吲哚基，苯并噻吩基，苯并呋喃基，苯并咪唑基，苯并噻二唑基，吲唑基，苯并三唑基，苯并噻唑基，苯并恶唑基，喹啉基，异喹啉基，酞嗪基，喹喔啉基，间二氮杂萘基，噌嗪基和萘啶基。每个可选地被1-3个相同或不同的R3取代基取代。
R1和R2均为氢；和
R3选自氰基，硝基，氟，氯，溴，碘，羟基，乙酸基，甲基，乙基，异丙基，叔丁基，二氟甲基，三氟甲基，甲氧基，乙氧基，二氟甲氧基，三氟甲氧基，甲硫基，异丙硫基，3-乙氧基-正-丙基，甲氧基甲基，2-甲氧基乙氧基，CH2-CN，C(O)OCH3，S(O)2CH3，NH2，N(CH3)2，OP(O)(CH2CH3)2，苯基，N-吡咯基，噻二唑基和吡啶基。
在第三个优选方面的一个更优选实施例中，本发明提供一种式(I)的化合物，其中
Q2是2,6-二氯-4-(九氟-丁-2-基)苯基；
Q1选自苯基，联苯基，呋喃基，吡啶基，噻吩基，噻二唑基，恶唑基，异恶唑基，噻唑基，异噻唑基，吡唑基和嘧啶碱基；每个可选地被1-3个相同或不同的R3取代基取代。
R1和R2均为氢；和
R3选自氰基，硝基，溴，氯，氟，甲基，乙基，三氟甲基，甲氧基和三氟甲氧基。
最有选的式(I)的化合物选自：
N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基-苯基]-3-(4-氰基-2-甲基苯甲酰氨基)-2-甲氧基苯甲酰胺(表A中A5号化合物)；
N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基苯基]-3-(4-氟-2-氯苯甲酰氨基)-2-甲氧基苯甲酰胺(表A中A3号化合物)；
N-[2-溴-6-氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)苯基]-3-(4-氟-2-氯苯甲酰氨基)-2-甲氧基苯甲酰胺(表B中B2号化合物)；
N-[2-溴-6-氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-苯基]-3-(4-氰基-2-甲基苯甲酰氨基)-2-甲氧基苯甲酰胺(表B中B1号化合物)；
N-[2,6-二氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)苯基]-3-(4-氟-2-氯苯甲酰氨基)-2-甲氧基苯甲酰胺(表C中C1号化合物)；
N-[2,6-二氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)苯基]-3-(4-氰基-2-甲基苯甲酰氨基)-2-甲氧基苯甲酰胺(表C中C2号化合物)；
N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基苯基]-3-(4-氟苯甲酰氨基)-2-甲氧基苯甲酰胺(表A中A1号化合物)；
N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基-苯基]-3-(4-氰基苯甲酰氨基)-2-甲氧基苯甲酰胺(表A中A4号化合物)；
N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基苯基]-3-(2-甲基-3-硝基苯甲酰氨基)-2-甲氧基苯甲酰胺(表A中A2号化合物)；及
N-{3-[2-溴-6-氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-苯氨羰基]-2-甲氧基苯基}-2,4,6-三氟苯甲酰胺(表B中B189号化合物)。
在另外一方面，本发明提供一种式(II)的化合物，
其中Q1，R1，R2和R3如式(I)以及与式(I)中Q1，R1，R2和R3相对应的优选实施例所定义；和
Q2选自：
2-乙基-6-甲基-4-(全氟异丙基)苯基，
2-溴-6-氯-4-(全氟异丙基)苯基，
2,6-二氯-4-(全氟异丙基)苯基，
2,6二甲基-4-(全氟异丙基)苯基，和
2-甲基-6-甲氧基甲基-4-(全氟异丙基)苯基。
在一个优选实施例中，本发明提供一种式(II)的化合物，其中
Q1选自苯基，联苯基，呋喃基，吡啶基，噻吩基，噻二唑基，恶唑基，异恶唑基，噻唑基，异噻唑基，吡唑基和嘧啶碱基；每个可选地被1-3个相同或不同的R3取代基取代。
R1和R2均为氢；和
R3选自氰基，硝基，溴，氯，氟，甲基，乙基，三氟甲基，甲氧基和三氟甲氧基；且
Q2选自
2-乙基-6-甲基-4-(全氟异丙基)苯基，
2-溴-6-氯-4-(全氟异丙基)苯基，
2,6-二氯-4-(全氟异丙基)苯基，
2,6二甲基-4-(全氟异丙基)苯基，和
2-甲基-6-甲氧基甲基-4-(全氟异丙基)苯基；
或农业上可接受的盐或其N-氧化物。
最优选的式(II)化合物为表E，G，J，K和L中化合物。
本发明化合物可通过多种方法制得，例如WO 08/000438中公开的方法。
1)式(I)化合物可利用式NHR2Q2的胺类来处理式(V)化合物制得，其中R是OH，C1-C6烷氧基，氯，氟或溴。如果R是OH，这些反应可以在一种耦合剂如DCC(N,N'-二环己基碳二亚胺)，EDC(1-乙基-3-[3-二甲基氨基-丙基]碳二亚胺盐酸盐)，或BOP-Cl(二(2-氧代-3-恶唑烷基)膦酰氯)的存在下，且在一种碱如吡啶，三乙胺，4-(二甲氨基)吡啶或二异丙基乙胺的存在下，以及可选地在一种亲核催化剂如羟基苯并三唑的存在下进行。若R是氯，这些反应可以在碱性条件下进行，例如在吡啶4-(二甲氨基)吡啶或二异丙基乙胺的存在下，且可选地在一种亲核催化剂的存在下进行。可替换地，本反应可以在包含一种有机溶剂优选为乙酸乙酯和一种水相溶剂优选为碳酸氢钠的两相系统中进行。若R是C1-C6烷氧基，可通过热法一起加热酯类和胺类物质，使酯直接转化成酰胺。
2)式(V)的酸性卤化物，其中R是氯，氟或溴，可从式(V)的羧酸中制得，其中R是用亚硫酰氯或乙二酰氯处理的OH。
3)其中R是OH的式(V)羧酸可形成于式(V)的酯类，其中R是经一种碱金属类氢氧化物如氢氧化钠在例如乙醇的溶剂中处理酯类物产生的C1-C6烷氧基。
4)其中R是C1-C6烷氧基的式(V)酯类，可在如1)中所述标准条件下经过处理式(IV)化合物而制得，其中R是用式Q1-COOH的羧酸或式Q1-COHal的酸性卤化物经酰化而成的C1-C6烷氧基，其中Hal是氯，氟或溴。
5)其中R是C1-C6烷氧基的式(IV)化合物，可用一种醇R-OH(在酸性条件下然后形成N-R1键)来顺序处理式(VI)化合物而制得。例如，可用醛或酮及例如氰基硼氢化钠的还原剂来对胺进行处理以实现还原性胺化。可替换地，可用一种烷化剂如卤代烷(可选地在碱的存在下)来对胺进行处理以实现烷化。可替换地，可用一种卤代芳烃或磺酸盐，在一种适宜的催化剂/配体系统(通常为钯(0)络合物)的存在下，对胺进行处理以实现芳化。
6)可替换地，其中R是C1-C6烷氧基的式(IV)化合物可从式(VII)化合物中通过用式R1-NH2的胺或其它亚胺类似物取代离去基团并随后用金属催化剂进行水解的方式制得，其中R是C1-C6烷氧基且LG是一个离去基团，如氟，氯或磺酸盐。可参考如ChemicalCommunications(2009),(14),1891-1893或Journal of Organic Chemistry(2000),65(8),2612-2614。
式(VII)化合物和式R1-NH2的胺类可为已知化合物，也可以是本领域技术人员可通过熟知的方法制得的化合物。
7)可替换地，式(I)化合物，可在如1)中所述标准条件下，通过用式Q1-COOH的羧酸或式Q1-COHal的酸性卤化物来处理式(IX)化合物制得，其中Hal是氯，氟或溴。
8)式(IX)化合物，可在如1)中所述标准条件下，从式(VIII)化合物中通过用式NHR2Q2的胺来形成酰胺键且随后去除保护基团P的方式制得，其中P是一种适宜的保护基团且R是OH，氯或C1-C6烷氧基。
9)其中R是OH或C1-C6烷氧基的式(VIII)化合物可在式(IV)化合物中胺类官能的保护下制得，其中R是OH或C1-C6烷氧基。适宜的保护基团包括氨基甲酸盐(如叔丁氧羰基，烯丙氧羰基和苄氧羰基)，三烷基甲硅烷基基团(如叔丁基二甲基硅烷)和酰基基团(如乙酰基)。
10)对于式(VIII)和式(IV)化合物，其中R是C1-C6烷氧基的酯类，可通过碱金属类氢氧化物如氢氧化钠在例如乙醇的溶剂中处理从而被水解成酸，其中R是OH。所述酸可通过如2)和3)中所述的亚硫酰氯或乙二酰氯来处理从而被转化成酸性氯化物，其中R是氯。
11)可替换地，其中R为OH，氯，氟，溴或C1-C6烷氧基的式(IV)化合物可在如1)所述的标准条件下通过式NHR2Q2的胺直接转化成式(IX)的化合物。
12)可替换地，式(IX)化合物可从式(XI)化合物中通过用式R1-NH2的化合物或其它亚胺类似物取代离去基团并随后用金属催化剂进行水解的方式制得，其中LG是一个离去基团，如碘，溴，氯或磺酸盐。可参考如Chemical Communications(2009),(14),1891-1893或Journal of Organic Chemistry(2000),65(8),2612-2614。
13)式(XI)化合物，可在如1)所述的标准条件下，通过形成酰胺键从式(X)化合物中制得，其中R是氯或OH且LG是如12)所述的离去基团。式(X)和(IV)中化合物可为已知化合物，也可以是本领域技术人员可通过熟知的方法制得的化合物。
14)其中R1是氢的式(IX)化合物的别种合成，可通过还原式(XIII)的硝基化合物实现，如在酸性条件下通过氯化锡来处理，或利用贵金属如钯炭催化剂进行氢化。
15)式(XIII)化合物，可在如1)所述的标准条件下，通过式NHR2Q2中胺来酰化的方式从式(XII)化合物中衍生，其中R是OH,Cl,或者C1-C6烷氧基。
16)对于式(XII)化合物，其中R是C1-C6烷氧基的酯类，可通过碱金属类氢氧化物如氢氧化钠在例如3)中所述的乙醇溶剂中处理从而被水解成酸，其中R是OH。所述酸可通过如2)中所述的亚硫酰氯或乙二酰氯来处理从而被转化成酸性氯化物，其中R是氯。式(XII)中化合物可为已知化合物，也可以是本领域技术人员可通过熟知的方法制得的化合物。
17)式(XII)化合物，可在碱(如NaH)的存在下从式(XIV)化合物与甲醇反应中制得，其中LG是卤素，如氟或氯。
也可用氧亲核试剂代替式(XIII)中间产物的卤素。
所述式(I)化合物可以用于对抗和防除虫害如鳞翅目(Lepidoptera)、双翅目(Diptera)、半翅目(Hemiptera)、缨翅目(Thysanoptera)、直翅目(Orthoptera)、网翅目(Dictyoptera)、鞘翅目(Coleoptera)、蚤目(Siphonaptera)、膜翅目(Hymenoptera)和等翅目(Isoptera)和还有其它无脊椎动物害虫例如蜱螨、线虫和软体动物害虫的侵染。昆虫、蜱螨、线虫和软体动物在下文统称为害虫。通过使用本发明化合物可以对抗和防除的害虫包括与农业(该术语包括用于食物和纤维产品的农作物的生长)、园艺学和畜牧业、陪伴动物、林业和植物来源产品(如果实、谷物和木材)的储藏相关的那些害虫；与人造建筑的损坏和任何动物疾病的传播相关的那些害虫；还有公害害虫(如蝇)。
可通过式(I)化合物防除的害虫物种的实例包括：桃蚜(Myzus persicae)(蚜虫)、棉蚜(Aphis gossypii)(蚜虫)、黑豆蚜(Aphis fabae)(蚜虫)、草盲蝽属(Lygus spp.)(盲蝽科)、棉红蝽属(Dysdercus spp.)(盲蝽科)、褐飞虱(Nilaparvata lugens)(飞虱)、黑尾叶蝉(Nephotettixc incticeps)(叶蝉)、绿蝽属(Nezara spp.)(蝽)、美洲蝽属(Euschistus spp.)(蝽)、稻缘蝽属(Leptocorisa spp.)(蝽)、西花蓟马(Frankliniellaoccidentalis)(蓟马)、蓟马属(Thrips spp.)(蓟马)、马铃薯叶甲(Leptinotarsadecemlineata)(科罗拉多薯虫)、棉铃象(Anthonomus grandis)(棉铃象鼻虫)、肾圆盾蛤属(Aonidietta spp.)(蛤)、粉虱属(Triateurodes spp.)(粉虱)、甘薯粉虱(Bemisiatabaci)(粉虱)、欧洲玉米螟(Ostrinia nubitatis)(玉米螟)、棉贪夜蛾(Spodopteralittoratis)(斜纹夜蛾)、烟芽夜蛾(Heliothis virescens)(烟青虫属)、美洲棉铃虫(Helicoverpa armigera)(棉铃虫)、谷实夜蛾(Helicoverpa zea)(棉铃虫)、棉卷叶野螟(Sylepta derogata)(棉卷叶螟)、欧洲粉蝶(Pieris brassicae)(粉蝶)、小菜蛾(Plutellaxylostella)(菜蛾)、地夜蛾属(Agrotis spp.)(切根虫)、二化螟(Chilo suppressalis)(水稻螟虫)、飞蝗(Locusta migratoria)(蝗虫)、澳洲草栖蝗(Chortiocetesterminifera)(蝗虫)、叶甲属(Diabrotica spp.)(根虫类)、苹果全爪螨(Panonychusulmi)(欧洲红蜘蛛)、柑橘全爪螨(Panonychus citri)(柑桔红蜘蛛)、二斑叶螨(Tetranychus urticae)(叶螨)、朱砂叶螨(Tetranychus cinnabarinus)(叶螨)、柑橘皱叶刺瘦螨(Phyllocoptruta oleivora)(柑橘锈螨)、侧多食跄线螨(Polyphagotarsonemuslatus)(广明螨)、短须螨属(Brevipalpus spp.)(螨属)、微小牛蜱(Boophilus microplus)(牛蚤)、变异革蜱(Dermacentor variabilis)(美洲犬蜱)、猫栉首蚤(Ctenocephalidesfelis)(猫蚤)、斑潜蝇属(Liriomyza spp.)(潜叶虫)、家蝇(Musca domestica)(家蝇)、埃及伊蚊(Aedes aegypti)(蚊子)、按蚊属(Anopheles spp.)(蚊子类)、库蚊属(Culex spp.)(蚊子类)、绿蝇属(Lucillias pp.)(丽蝇)、德国小蠊(Blattella germanica)(蜚蠊)、美洲大蠊(Periplaneta americana)(蜚蠊)、东方蜚蠊(Blatta orientalis)(蜚蠊)、澳白蚁科白蚁(Mastotermitidae)(例如澳白蚁属)(Mastotermes spp.)、木白蚁科(Kalotermitidae)(例如新白蚁属)(Neotermes spp.)、鼻白蚁科(Rhinotermitidae)(例如台湾乳白蚁(Coptotermes formosanus)、欧美散白蚁(Reticulitermes flavipes)、栖北散白蚁(R.speratu)、美小黑散白蚁(R.virginicus)、西美散白蚁(R.hesperus)、和桑特散白蚁(R.santonensis))及自蚁科(Termitidae)(例如黄球白蚁)(Globitermes sulfureus)、火蚁(Solenopsis geminata)(火蚁)、小家蚁(Monomorium pharaonis)(厨蚁)、畜虱属(Damalinia spp.)和长颚虱属(Linognathus spp.)(咬虱和吸血虱)、根结线虫属(Meloidogyne spp.)(根结线虫)、球异皮线虫属(Globodera spp.)和异皮线虫属(Heterodera spp.)(包曩线虫)、短体线虫属(Pratylenchus spp.)(根斑线虫)、粉褶菌属(Rhodopholus spp.)(香蕉穿孔线虫)、小垫刀线虫属(Tylenchulus spp.)(柑橘线虫)、捻转血茅线虫(Haemonchus contortus)(管圆线虫)、秀丽隐杆线虫(Caenorhabditiselegans)(醋线虫)、毛圆线虫属(Trichostrongylus spp.)(胃肠道线虫)和网纹野蛞蝓(Deroceras reticulatum)(蛞蝓)。
本发明因此提供对抗和防除昆虫、蜱螨、线虫或软体动物的方法，其包括施用杀昆虫、杀螨、杀线虫或杀软体动物有效量的式(I)化合物或包含式(I)化合物的组合物至害虫、害虫所在处(优选植物)或施用至易受害虫侵染的植物，所述式(I)化合物优选用于对抗昆虫或蜱螨。
在此使用的所述术语“植物”包括幼苗、灌木和树。
农作物被理解为还包括由常规育种方法或基因工程使之耐受除草剂或除草剂类别(例如ALS-、GS-、EPSPS-、PPO-和HPPD抑制剂)的那些农作物。通过常规的育种方法使之耐受咪唑啉酮类例如甲氧咪草烟的农作物的实例是夏播油菜(油菜)。通过基因工程方法使之耐受除草剂的农作物的实例包括以商品名称和市售的草甘膦-和草铵膦-抗性玉米品种。
农作物还被理解为是通过基因工程方法使之抗有害昆虫的那些，例如Bt玉米(抗欧洲玉米螟)、Bt棉花(抗棉铃象)和Bt马铃薯(抗马铃薯叶甲)。Bt玉米的实例是(Syngenta种子)的Bt 176玉米杂交种。包含一个或多个编码杀昆虫剂抗性的基因并表达一个或多个毒素的转基因植物的实例是(玉米)、Yield(玉米)、(棉花)、(棉花)、(马铃薯)、和
植物农作物或其种子材料可以同时是抗除草剂和抗昆虫取食的(“叠加的”转基因事件)。例如种子可以具有表达杀昆虫的Cry3蛋白质的能力，同时是耐受草甘膦的。
农作物还被理解为是通过常规的育种方法或基因工程所获得并包含所谓的产出性状(例如提高的储藏稳定性、较高的营养值和改善的香味)的那些。
为了将作为杀昆虫剂、杀螨剂、杀线虫剂或杀软体动物剂的式(I)化合物施用至害虫、害虫所在处，或施用至易受害虫侵染的植物，通常将式(I)化合物配制成组合物，其除所述式(I)化合物之外，包括适宜的惰性稀释剂或载体和可选地包括表面活性剂(SFA)。SFA是能够通过降低界面张力改变界面(例如液体/固体、液体/空气或液体/液体界面)的性质并经此导致其它性质(例如分散、乳化和润湿)的改变的化学品。优选的是，所有组合物(固体和液体配制剂这两者)包含基于重量的0.0001-95％，更优选1-85％，例如5-60％的式(I)化合物。所述组合物通常如此用于害虫的防除，将式(I)化合物以0.lg-l0kg每公顷，优选1g-6kg每公顷，更优选1g-1kg每公顷的量施用。
如果用于种衣剂，式(I)化合物以每公斤种子0.0001g-10g(例如0.001g或0.05g)，优选0.0058-10g，更优选0.0058-4g的量使用。
在另一方面，本发明提供杀昆虫的、杀螨的、杀线虫的或杀软体动物的组合物，其包含杀昆虫、杀螨、杀线虫或杀软体动物有效量的式(I)化合物和为此的适宜的载体或稀释剂。所述组合物优选是杀昆虫的、杀螨的、杀线虫的或杀软体动物的组合物。
所述组合物可选自大量配制剂类型，包括粉剂(DP)、可溶性粉剂(SP)、水溶性粒剂(SG)、水分散粒剂((WG)、可湿性粉剂(WP)、颗粒剂(GR)(缓释或速释)、可溶性浓缩物(SL)、油剂(OL)、超低容量液剂(UL)、乳油(EC)、可分散液剂(DC)、乳液(水包油(EW)和油包水(EO))、微乳剂(ME)、悬浮剂(SC)、气雾剂、发雾/发烟配制剂、微囊悬浮剂(CS)和种子处理配制剂。所选择的配制剂类型在任何情况下都取决于所面临的具体目的和所述式(I)化合物的物理、化学和生物性质。
粉剂(DP)的制备可以如下进行，即通过将式(I)化合物与一种或多种固体稀释剂(例如天然粘土、高岭土、叶蜡石、膨润土、矾土、蒙脱土、硅藻土、白奎、硅藻土、磷酸钙、碳酸钙和碳酸镁、硫、石灰、面粉、滑石粉和其它有机的和无机的固体载体)混合并机械研磨该混合物至细粉。
可溶性粉剂(SP)的制备可以如下进行，即通过将式(I)化合物与一种或多种水溶性无机盐(如碳酸氢钠、碳酸钠或硫酸镁)或一种或多种水溶性有机固体(如多糖类)和，可选地，一种或多种润湿剂、一种或多种分散剂或所述试剂的混合物混合，以提高水分散性/溶解性。然后将所述混合物研磨至细粉末。还可以粒化相似的组合物以形成水溶性粒剂(SG)。
可湿性粉剂(WP)的制备可以如下进行，即通过将式(I)化合物与一种或多种固体稀释剂或载体、一种或多种润湿剂和优选一种或多种分散剂和可选地促进在液体中的分散的一种或多种防沉降剂混合。然后将所述混合物研磨至细粉末。还可以粒化相似的组合物以形成水分散粒剂(WG)。
颗粒剂(GR)的形成可以通过粒化式(I)化合物与一种或多种粉末化的固体稀释剂或载体的混合物进行，或者由预成型的空白颗粒通过将式(I)化合物(或其在适宜试剂中的溶液)吸入多孔粒状材料(如浮石、绿坡缕石粘土、漂白土、硅藻土、硅藻土或磨碎的玉米轴)中或通过将式(I)化合物(或其在适宜试剂中的溶液)吸附在硬质核心的材料(如细砂、硅酸盐、矿物碳酸盐、硫酸盐或磷酸盐)上并按需要进行干燥。常用于帮助吸收或吸附的试剂包括溶剂(如脂族和芳族的石油溶剂、醇、醚、酮和酯)和粘着剂(如聚乙酸乙烯酯、聚乙烯醇、糊精、糖和植物油)。一种或多种其它添加剂也可以被包含于颗粒剂中(例如乳化剂、润湿剂或分散剂)。
可分散液剂(DC)的制备可以通过将式(I)化合物溶解于水或有机溶剂如酮、醇或乙二醇醚中进行。这些溶液可以包含表面活性剂(例如用以在喷雾桶中提高水稀释性或避免结晶)。
乳油(EC)或水包油乳液(EW)的制备可以通过将式(I)化合物溶解于有机溶剂(可选地包含一种或多种润湿剂、一种或多种乳化剂或所述试剂的混合物)进行。对于在EC中使用的适宜的有机溶剂包括芳族烃类(如烷基苯或烷基萘，示例为SOLVESSO100、SOLVESSO150和SOLVESSO 200；SOLVESSO为注册商标)，酮类(如环己酮或甲基环己酮)和醇类(如苯甲醇、糠醇或丁醇)，N-烷基吡咯烷酮类(如N-甲基吡咯烷酮或N-辛基吡咯烷酮)，脂肪酸的二甲基酰胺(如C8-C10脂肪酸二甲酰胺)和氯代烃类。在添加水的情况下，EC产品可以自发地乳化产生具有足够稳定性的乳液以允许通过适当的设备喷雾施用。EW的制备涉及获取呈液体(如果其在室温下不是液体，可以熔融于合理温度下，典型地低于70℃)或在溶液中(通过将其溶解于适当的溶剂中)的式(I)化合物，然后在高剪切力下将所获得的液体或溶液乳化入含一种或多种SFA的水中，产生乳液。在EW中使用的适宜的溶剂包括植物油、氯代烃(如氯苯)，芳族的溶剂(如烷基苯或烷基萘)和在水中具有低溶解度的其它适当的有机溶剂。
微乳剂(ME)的制备可以通过将水和一种或多种溶剂与一种或多种SFA的共混物混合自发产生热动力学稳定的各向同性的液体配制剂而进行。式(I)化合物起初存在于水或溶剂/SFA共混物中。在ME中使用的适宜的溶剂包括此前描述于EC或EW中使用的那些。ME可以是水包油或油包水体系(存在哪种体系可由导电率测量来确定)并且可以适用于在同一配制剂中混合水溶和油溶的农药。ME适用于稀释进水中，保持为微乳剂或形成传统的水包油乳液。
悬浮剂(SC)可以包括式(I)化合物的细分散的不溶固体颗粒的含水或无水悬浮液。SC的制备可以通过在适宜的介质、可选地和一种或多种分散剂中球磨或珠磨固体式(I)化合物进行以产生所述化合物的细粒悬浮液。一种或多种润湿剂可以包含于所述组合物中并且可以包含防沉降剂以降低颗粒沉降率。可替代地，可以干磨式(I)化合物并加至包含此前所述的试剂的水中，以产生所希望的终产品。
气雾配制剂包含式(I)化合物和适宜的推进剂(例如正-丁烷)。式(I)化合物还可以溶解于或分散于适宜的介质中(例如水或水可混的液体，如正-丙醇)以提供在非加压的、手动的喷雾泵中使用的组合物。
式(I)化合物可以在干燥状态下与烟火混合物混合以形成适用于在封闭空间内产生包含所述化合物的烟雾的组合物。
微囊悬浮剂(CS)可以以相似于EW配制剂的方式制备但具有额外的聚合反应阶段以获得小油滴的水性分散液，其中每个小油滴被聚合物壳包囊并包含式(I)化合物和可选地其载体或稀释剂。所述聚合物壳可以由界面缩聚反应或通过凝聚过程制备。所述组合物可提供控释的所述式(I)化合物并且它们可以用于种子处理。式(I)化合物还可以配制在生物可降解的聚合物基质中以提供缓控释的化合物。
组合物可以包含一种或多种添加剂以提高所述组合物的生物性能(例如通过提高在表面上的润湿性、滞留或分布；经处理的表面上的耐雨性；式(I)化合物的吸收和流动性)。这样的添加剂包括表面活性剂、油基的喷雾添加剂，例如特定的矿油或天然植物油(如大豆和油菜籽油)，和它们与其它生物一强化佐剂(可有助于或改变式(I)化合物的活性的成分)的混合物。
式(I)化合物还可以配制为用作种子处理剂，例如作为粉末组合物，包括干拌种剂(DS)、水溶性粉剂(SS)或种子处理可分散性粉剂(WS)，或作为液体组合物，包括悬浮种衣剂(FS)、种衣用溶液(LS)或微囊悬浮剂(CS)。DS、SS、WS、FS和LS组合物的制备分别很相似于以上描述的DP、SP、WP、SC和DC组合物。用于处理种子的组合物可以包含用于协助将所述组合物粘附到种子上的试剂(例如矿油或成膜阻隔剂)。
润湿剂、分散剂和乳化剂可以是阳离子型、阴离子型、两性型或非离子型的SFA。
适宜的阳离子型SFA包括季胺化合物(例如鲸蜡基三甲基铵溴化物)、咪唑啉和胺盐。
适宜的阴离子型SFA包括脂肪酸的碱金属盐、硫酸的脂族单酯盐(例如月桂基硫酸钠)、磺酸化芳族化合物的盐(例如十二烷基苯磺酸钠、十二烷基苯磺酸钙、丁基萘磺酸盐和二-异丙基-与三-异丙基-萘磺酸钠的混合物)、醚硫酸盐、醇醚硫酸盐(例如月桂醇聚醚-3-硫酸钠)、醚羧酸盐(例如月桂醇聚醚-3-羧酸钠)、磷酸酯盐(由一种或多种脂肪醇与磷酸反应的产物(主要是单酯)或与五氧化二磷反应的产物(主要是二酯)，例如月桂醇与四磷酸的反应；此外这些产物可以是乙氧基化的)、磺基琥珀酰胺酸盐、烷烃或烯烃磺酸盐、牛磺酸盐和木质素磺酸盐。
适宜的两性型SFA包括甜菜碱、丙酸类和甘氨酸类。
适宜的非离子型SFA包括环氧烷烃如环氧乙烷、环氧丙烷、环氧丁烷或它们的混合物与脂肪醇(如油醇或鲸蜡醇)或者与烷基酚类(如辛基酚、壬基酚或辛基甲酚)的缩合产物；衍生自长链脂肪酸或己糖醇配的偏酯；所述偏酯与环氧乙烷的缩合产物；嵌段聚合物(包含环氧乙烷和环氧丙烷)；烷醇酰胺；简单酯类(例如脂肪酸聚乙二醇酯)；氧化胺(例如月桂基二甲基氧化胺)；和卵磷脂。
适宜的防沉降剂包括亲水胶体(如多糖类，聚乙烯基吡咯烷酮或羧甲基纤维素钠)和膨胀性粘土(如膨润土或绿坡缕石)。
式(I)化合物可以通过任何已知的施用杀虫化合物的手段进行施用。例如可以经配制或不经配制地施用到害虫或害虫的所在地(如害虫的栖息地、或易受害虫侵染的生长中的植物)或植物的任何部分，包括叶、茎干、枝权或根，在种植前施用到种子或其中植物生长或待种植的其它介质(如根周围的土壤、一般性土壤、水稻用水或溶液栽培体系)中，或者可以喷雾、喷粉、通过浸渍施用、作为霜剂或糊剂配制剂施用、作为蒸汽施用或通过将组合物(如粒状组合物或装入水溶性袋的组合物)分布或引入土壤或水环境中施用。
式(I)化合物还可以注入植物中或用电动喷雾技术或其它低容量方法喷雾到植被上，或通过土地灌溉或空中灌溉系统施用。
用作含水制剂(水溶液或分散液)的组合物通常以浓缩物的形式提供，所述浓缩物包含高比例的活性成分，所述浓缩物在使用前加入水中。这些可包括DC、SC、EC、EW、ME、SG、SP、WP、WG和CS的浓缩物，经常被要求能经受住旷日持久的储存，并且在这样的储存后能够加入水中以形成保持均质足够时间的含水制剂以使得它们能够通过传统的喷雾设备施用。取决于它们待使用的目的，这样的含水制剂可以包含变化量的式(I)化合物(例如0.0001-10重量％)。
式(I)化合物可以在与肥料(例如含氮、钾或磷的肥料)的混合物中使用。适宜的配制剂类型包括肥料的颗粒剂。所述混合物优选包含直至25重量％的所述式(I)化合物。
因此本发明还提供包含肥料和式(I)化合物的肥料组合物。
本发明的所述组合物可以包含具有生物活性的其它化合物，例如微量营养素或具有杀真菌活性的化合物或者具有植物生长调节的、除草的、杀昆虫的、杀线虫的或杀螨虫的活性的化合物。
所述式(I)化合物可以是所述组合物的唯一活性成分或者适当时可以与一种或多种额外的活性成分如杀虫剂、杀真菌剂、增效剂、除草剂或植物生长调节剂混合。额外的活性成分可以：提供对于处所具有较宽活性谱或增加持久性的组合物；增效或补充所述式(I)化合物活性(例如通过增加起效速度或克服排斥性)；或者协助克服或防止对单个组分的抗性发展。具体的额外活性成分将取决于所述组合物的目标用途。适宜杀虫剂的实例包括：
a)拟除虫菊酯，如氯菊酯、氯氰菊酯、氰戊菊酯、S-氰戊菊酯、溴氰菊酯、氯氟氰菊酯(特别是入一氯氟氰菊酯)、联苯菊酯、甲氰菊酯、氟氯氰菊酯、七氟菊酯、对鱼类无害的拟除虫菊酯(例如醚菊酯)、天然的除虫菊酯、胺菊酯,S-生物烯丙菊酯、芬氟司林、右旋炔丙菊酯或5-节基-3-呋喃基甲基-(E)-(1R,3R)-2,2-二甲基-3-(2-氧代硫杂环戊烷-3-亚基甲基)环丙烷羧酸酯；
b)有机磷酸盐，如丙溴磷、硫丙磷、乙酰甲胺磷、甲基对硫磷、保棉磷、甲基内吸磷、庚烯磷、甲基乙拌磷、苯线磷、久效磷、丙溴磷、三唑磷、甲胺磷、乐果、磷胺、马拉硫磷、毒死蜱、伏杀硫磷、特丁磷、丰索磷、地虫硫磷、甲拌磷、辛硫磷、甲基嘧啶磷、乙基嘧啶磷、杀螟硫磷、噻唑磷或二嗪磷；
c)氨基甲酸酯(包括芳基氨基甲酸酯)，如抗蚜威、唑蚜威、除线威、克百威、呋线威、乙硫苯威、涕灭威、久效威、丁硫克百威、恶虫威、仲丁威、残杀威、灭多威或草氨酰；
d)苯甲酰脲类，如除虫脲、杀铃脲、氟铃脲、氟虫脲或氟啶脲；
e)有机锡化合物，如三环锡、苯丁锡或三唑锡；
f)吡唑类，如吡螨胺和唑螨酯；
g)大环内酯类，如除虫菌素类或米尔倍霉素类，例如阿巴克丁、埃玛菌素、伊维菌素、米尔倍霉素、多杀菌素、印楝素或乙基多杀菌素；
h)激素类或信息素类；
i)有机氯化合物如硫丹(特别是α-硫丹)、六六六、DDT、氯丹或狄氏剂；
j)脒类，如杀虫脒或阿米曲士；
k)熏剂类，如氯化苦、二氯丙烷、溴甲烷或威百亩
l)新烟碱类化合物如吡虫啉、噻虫啉、啶虫脒、尼藤吡蓝、呋虫胺、噻虫嗪、噻虫胺、硝虫噻嗪或氟啶虫酰胺
m)二酰基类，如虫酰肼、环虫酰肼或甲氧虫酰肼；
n)二苯醚类，如苯虫醚或吡丙醚
o)茚虫威；
p)溴虫腈；
q)吡蚜酮；
r)螺虫乙酯、螺螨酯或螺甲螨酯；或者
s)二酰氨类，如氟虫酰胺，氯虫酰胺或氰虫酰胺；
t)氟啶虫胺腈；或
u)氰氟虫腙。
除上述所列的主要化学类别的杀虫剂之外，如果适合于所述组合物的目的用途，其它具有特定标靶的杀虫剂可以用于所述组合物中。例如，用于特定农作物的选择性杀昆虫剂，例如可以采用钻心虫特效杀昆虫剂(如杀螟丹)或跳虫特效杀昆虫剂(如噻嗪酮)用于稻谷。可替代地，针对特定昆虫种类/阶段的杀昆虫剂或杀螨虫剂特效也可以包括于所述组合物中(例如杀螨虫的杀卵-杀幼虫剂，如四螨嗪、氟螨噻、噻螨酮或三氯杀螨砜；杀螨虫的抑虫剂，如三氯杀螨醇或炔螨特；杀螨虫剂，如溴螨酯或乙酯杀螨醇；或生长调节剂，如氟蚁踪、灭蝇胺、烯虫酯、氟啶脲或除虫脲)。
可以包括于本发明的所述组合物的杀真菌的化合物的实例是(E)-N-甲基-2-[2-(2,5-二甲基苯氧基甲基)苯基-2-甲氧基-亚氨基乙酰胺(SSF-129)，4-嗅-2-氰基-N,N-二甲基-6-三氟甲基苯并咪唑-1-磺酰胺，α-[N-(3-氯-2,6-二甲基苯基)-2-甲氧基乙酰氨基]-γ-丁内酯，4-氯-2-氰基-N,N-二甲基-5-p-甲基苯基咪唑-1-磺酰胺(IKF-916，氰唑磺菌胺)，3,5-二氯-N-(3-氯-1-乙基-1-甲基-2-氧代丙基)-4-甲基苯甲酰胺(RH-7281，苯酰菌胺)，N-烯丙基-4,5-二甲基-2-三甲基甲硅烷基噻吩-3-甲酰胺(MON65500)，N-(1-氰基-1,2-二甲基丙基)-2-(2,4-二氯苯氧基)丙酰胺(AC382042)，N-(2甲氧基5吡啶基)环丙烷甲酰胺，活化酯(CGA245704)，棉铃威，杀螟丹，敌菌灵，阿扎康唑，嘧菌酯，苯霜灵，苯菌灵，双苯三唑醇，联苯三唑醇，灭瘟素，糠菌唑，乙嘧酚磺酸酯，敌菌丹，克菌丹，多菌灵，多菌灵盐酸盐，萎锈灵，环丙酰菌胺，香芹酮，CGA41396,CGA41397，灭螨猛，百菌清，乙菌利，外消旋杀真菌剂，含铜化合物如王铜，羟基喹啉铜，硫酸铜，妥尔铜和波尔多液，霜脲氰，环丙唑醇，嘧菌环胺，咪菌威，二-2-酰啶基二硫化物1,1-二氧化物，苯氟磺胺，哒菌酮，氯硝胺，乙霉威，苯醚甲环唑，野燕枯，氟嘧菌胺，O,O-二-异-丙基-S-苄基硫代磷酸酯，二甲基噻唑，恶醚唑，烯酰吗啉，二甲嘧酚，烯唑醇，二硝巴豆酸酯，二氰蒽醌，十二烷基二甲基氯化胺，十二环吗啉，多果定，多果定，敌瘟磷，氟环唑，乙嘧酚，(Z)-N-苄基-N([甲基(甲基-硫代亚乙基氨基氧基羰基)氨基]硫代)-β-氨基丙酸乙酯，土菌灵，恶唑菌酮，咪唑菌酮(RPA407213)，氯苯嘧啶醇，腈苯唑，甲呋酰胺，环酰菌胺(KBR2738)，拌种咯，苯锈啶，丁苯吗啉，三苯基乙酸锡，三苯基氢氧化锡，福美铁，嘧菌腙，氟啶胺，咯菌腈，氟酰菌胺，氟氯菌核利，氟喹唑，氟硅唑，氟酰胺，粉唑醇，灭菌丹，麦穗宁，呋霜灵，呋吡菌胺，双胍辛乙酸盐，己唑醇，羟基异恶唑，恶霉灵，抑霉唑，亚胺唑，双胍辛胺，双胍辛胺乙酸盐，种菌唑，异稻瘟净，异菌脲，异丙菌胺(SZX0722)，异丙基丁基氨基甲酸酯，稻瘟灵，春雷霉素，醚菌酯，LY186054，LY211795，LY248908，代森锰锌，代森锰，精甲霜灵，嘧菌胺，灭锈胺，甲霜灵，叶菌唑，代森联，代森联-锌，苯氧菌胺，腈菌唑，田安，二甲氨基二硫代甲酸镍，酰菌酯，氟苯嘧啶醇，呋酰胺，有机汞化合物，恶霜灵，环氧嘧磺隆，喹菌酮，恶咪唑，氧化萎锈灵，稻瘟酯，戊菌唑，戊菌隆，叶枯净，乙磷铝，亚磷酸类，四氯苯酰，啶氧菌酯(ZA1963)，多抗霉素D，代森联，烯丙苯噻唑，咪酰胺，腐霉利，霜霉威，丙环唑，丙森锌，丙酸，吡菌磷，啶斑肟，嘧霉胺，咯喹酮，氯吡呋醚，吡咯尼群，季铵化合物，灭螨猛，苯氧喹啉，五氯硝基苯，菌唑(F-155)，五氯酚钠，螺环菌胺，链霉素，硫，戊唑醇，叶枯酰，四氯硝基苯，四氟醚唑，噻菌灵，噻氟菌胺，2-(氰硫基甲硫基)苯并噻唑，甲基硫菌灵，塞仑，酰胺唑，甲基立枯磷，甲苯氟磺胺，三唑酮，三唑醇，叶锈特，咪唑嗪，三环唑，十三吗啉，肟菌酯(CGA279202)，嗪氨灵，氟菌唑，灭菌唑，有效霉素A，威百亩，乙烯菌核利，代森锌和福美锌。
所述式(I)化合物可以与土壤、泥煤或其它生根介质混合用于保护植物对抗种子传播的、土壤传播的或叶的真菌疾病。
用于所述组合物的适宜的增效剂的实例包括增效醚，增效菊，增效散和十二烷基咪唑。
包含于所述组合物中的适宜的除草剂和植物--生长调节剂将取决于指定目标和所要求的效果。
可以被包含在内的稻谷选择性除草剂的实例是敌稗。用于棉花的植物生长调节剂的实例是PIXTM。
某些混合物可以包含具有显著不同的物理、化学或生物性质的活性成分，以致它们不易于使得它们本身成为同一传统的配制剂类型。在这些情况下，可以制备其它配制剂类型。例如，在其中一种活性成分为水不溶性的固体而另一种是水不溶性的液体的情况下，尽管如此仍可以使每种活性成分分散在同一连续水相是可能的，即通过将固体活性成分分散为悬浮液(使用相似于SC的制备)而将液体活性成分分散为乳液(使用相似于EW的制备)。所得到的组合物为悬乳剂(SE)配制剂。
实例
本节所用的缩写的意思如下所列：s＝单态；bs＝宽单态；d＝双态；dd＝双重双态；dt＝双重三态；t＝三态，tt＝三重三态，q＝四态，sept＝七态；m＝多态；Me＝甲基；Et＝乙基；Pr＝丙基；Bu＝丁基；M.p.＝熔点；RT＝保留时间，MH+＝分子氧离子(如所测分子量)。
实例I1:N-[2-溴-6-氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)苯基]-2-氟-3- 硝基苯甲酰胺
向2-溴-6-氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)苯胺(实例I6)(20g,47.1mmol)和2-氟-3-硝基苯甲酸(17.4g,94.2mmol)在二氯甲烷(230ml)的溶液中加入三乙胺(19.7ml,141mmol)和双(2-氧代-3-恶唑烷基)膦酰氯(“BOP-Cl”)(23.98g,94mmol)。将反应混合物加热回流6小时。待冷却至环境温度后加入盐酸水溶液(1N)淬火。然后用二氯甲烷萃取该混合物三次。用饱和的碳酸氢钠溶液来洗涤有机萃取物，再用硫化钠进行干燥并浓缩。残余物通过柱色谱法在硅胶上纯化(洗脱液：环己烷/乙酸乙酯7:3)，获得N-[2-溴-6-氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)苯基]-2-氟-3-硝基苯甲酰胺(12g,43％产率)。1H NMR(CDCl3,400MHz):8.48(t,1H),8.30(t,1H),8.18(db,1H),7.86(s,1H),7.75(s,1H),7.54(t,1H)ppm.
通过同样的方法制得下列化合物：
N-[2,6-二氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)苯基]-2-氟-3-硝基-苯甲 酰胺
1H NMR(CDCl3,400MHz):8.48(t,1H),8.28(t,1H),8.14(db,1H),7.68(s,2H),7.54(t,1H)ppm.
实例I2:N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基-苯基]-2- 氟-3-硝基苯甲酰胺
在环境温度下，向2-氟-3-硝基苯甲酸(6.3g,34mmol)在二氯甲烷(20ml)的悬浮液中加入乙二酰氯(4.3ml)，随后加入N,N二甲基甲酰胺(0.2ml)。于环境温度下搅拌反应混合物1小时后加热回流3小时。将反应混合物冷却至环境温度后浓缩。残余物悬浮在四氢呋喃(50ml)中。将2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基苯胺(其制备如WO08/074427中所述)(10g,28.3mmol)溶解于四氢呋喃(50ml)中，并加入吡啶(6.8ml,84.9mmol)进行反应。于环境温度下搅拌反应混合物3小时，然后再回流3小时。加入饱和的碳酸氢钠溶液(100ml)淬火，并用乙酸乙酯(2x 200ml)萃取混合物两次。用硫酸钠干燥所述有机萃取物并浓缩。残余物通过柱色谱法在硅胶上纯化(洗脱液：环己烷/乙酸乙酯4:1to0:1)，获得N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基-苯基]-2-氟-3-硝基苯甲酰胺(6.32g,43％产率)。
1H NMR(CDCl3,400MHz):8.34(m,1H),8.22(m,1H),8.02(bs,1H),7.45(t,1H),7.48(s,2H),2.70(q,2H),1.22(t,3H).
实例I3:N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基-苯基]-2- 溴-3-硝基苯甲酰胺
在环境温度下，向2-溴-3-硝基苯甲酸(2.870g,0.0117mol)在甲苯(29ml)的悬浮液中加入N,N-二甲基酰胺(90μl)，随后缓慢加入亚硫酰氯(1.69ml,0.02332mol)。于100℃搅拌反应混合物1小时。将其冷却至环境温度且蒸发掉甲苯。将适量酰基氯溶解于THF中，无需额外净化。
在0到5℃温度下，向2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基苯胺(其制备如WO 08/074427中所述)(106mg,0.3mmol)在四氢呋喃(0.5ml)溶液中添加吡啶(72.6μl,0.9mmol)。再向四氢呋喃(0.5ml)中添加2-溴-3-硝基苯甲酰氯(87mg,0.33mmol)溶液。于环境温度下搅拌反应混合物3小时，然后回流15小时。回流过后反应并未完成，继续添加N,N-二甲基乙酰胺(“DMA”)(0.1当量)以及更多的2-溴-3-硝基苯甲酰氯。于环境温度下搅拌反应混合物41小时。之后，加入饱和的碳酸氢铵溶液(10ml)淬火，并用乙酸乙酯(2x20ml)萃取混合物两次。用硫酸钠干燥所述有机萃取物并浓缩。残余物通过柱色谱法在硅胶上纯化(洗脱液：环己烷/乙酸乙酯6:1)，获得N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基-苯基]-2-溴-3-硝基苯甲酰胺(0.133g,76％产率)。
1H NMR(CDCl3,400MHz):7.78(dd,1H),7.72(dd,1H),7.53(t,1H),7.32(s,2H),7.17(bs,1H),2.71(q,2H),2.40(s,3H),1.19(t,3H).
实例I4:N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基-苯基]-2- 甲氧基-3-硝基苯甲酰胺
在环境温度下，向N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基苯基-2-氟-3-硝基苯甲酰胺(实例I2)(5g,9.6mmol)在甲醇(195ml)的溶液中添加碳酸钾(2.6g,16.2mmol)。在环境温度下搅拌反应混合物16小时。浓缩反应混合物并将残余物溶解于二氯甲烷中。用水洗涤有机相，且用硫酸钠干燥并浓缩。残余物通过柱色谱法在硅胶上纯化(洗脱液：环己烷/乙酸乙酯3:1)，获得N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基-苯基]-2-甲氧基-3-硝基苯甲酰胺(5.1g,99％产率)。1H NMR(400MHz,CDCl3):8.90(bs,1H),8.32(d,1H),7.97(d,1H),7.38(m,3H),4.19(s,3H),2.70(q,2H),2.24(s,3H),1.20(t,3H)ppm.
通过同样的方法制得下列化合物：
N-[2-溴-6-氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)苯基]-2-甲氧基-3-硝基 苯甲酰胺
1H NMR(400MHz,CDCl3):9.23(bs,1H),8.45(dd,1H),8.07(dd,1H),7.84(s,1H),7.71(s,1H),7.46(t,1H),4.18(s,3H)ppm.
N-[2,6-二氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)苯基]-2-甲氧基-3-硝基 苯甲酰胺
1H NMR(400MHz,CDCl3):9.22(bs,1H),8.42(d,1H),8.07(d,1H),7.68(s,2H),7.44(t,1H),4.15(s,3H)ppm.
类似的方法用于经N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基苯基]-2-溴-3-硝基苯甲酰胺(Example I3)来制备N[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基苯基]-2-甲氧基-3-硝基苯甲酰胺(92％产率)
实例I5:3-氨基-N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基苯 基]-2-甲氧基苯甲酰胺
在环境温度下，向N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基苯基]-2-甲氧基-3-硝基苯甲酰胺(实例I4)(5.1g,9.57mmol)在异丙醇(50ml)的溶液中添加氯化物(6.5g,34.5mmol)。将混合物冷却至0℃并缓慢加入浓缩的盐酸溶液(10ml)。在80℃下搅拌反应混合物半小时。蒸发掉三分之一体积的异丙醇。向浓缩混合物中加入水(100ml)并加入氢氧化钠水溶液(4N)调节其pH值至7至8。用乙酸乙酯(3x 200ml)萃取水相三次。用硫酸钠干燥有机相萃取物并浓缩。残余物通过柱色谱法在硅胶上纯化(洗脱液：环己烷/乙酸乙酯2:1至1:1)，获得3-氨基-N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基苯基]-2-甲氧基苯甲酰胺(2.3g,48％产率)。
1H NMR(400MHz,CDCl3):9.12(bs,1H),7.37(dd,1H),7.26(s,2H),6.91(t,1H),6.80(dd,1H),3.90(bs,2H),3.80(s,3H),2.60(q,2H),2.24(s,3H),1.11(t,3H)ppm.
通过同样的方法制得下列化合物：
3-氨基-N-[2-溴-6-氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-苯基]-2-甲氧 基苯甲酰胺
1H NMR(400MHz,CDCl3):7.73(bs,1H),7.61(s,1H),7.47(dd,1H),6.98(t,1H),6.88(dd,1H),3.91(s,3H),3.85(bs,2H)ppm.
3-氨基-N-[2,6-二氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-苯基]-2-甲氧基 苯甲酰胺
1H NMR(400MHz,CDCl3):7.65(s,2H),7.54(d,1H),7.10(t,1H),6.98(d,1H),3.98(s,3H),3.93(bs,2H)ppm.
实例I6:2-溴-6-氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-苯胺
将4-(1,2,2,3,3,3-六氟-1-三氟甲基乙基)苯胺(根据EP 1,006,102中方法制备)(175.8g,565mmol)溶解于乙腈(1000ml)中并添加N-氯-琥珀酰亚胺(“NCS”)(76.2g,570.7mmol)。加热回流反应混合物90分钟。在真空中浓缩反应混合物，残余物悬浮于乙醚中并过滤掉固体。浓缩滤液，残余物通过柱色谱法在硅胶上纯化(洗脱液：环己烷/二氯甲烷9:1)，获得2-氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-苯胺。将N溴代琥珀酰亚胺(“NBS”)(100.5g,565mmol)用作反应试剂，再重复一遍该程序。将这次的残余物通过柱色谱法在硅胶上纯化(洗脱液：环己烷/二氯甲烷2:1)，获得2-溴-6-氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-苯胺(143.3g,59.7％产率)。1H NMR(400MHz,CDCl3):7.70(s,1H),7.42(s,1H),4.82(s,2H)ppm.
实例I7:4-氰基-2-甲基苯甲酸甲酯
在氮气氛下，向4-溴-2-甲基苯甲酸(108g,471mmol)在N,N二甲基甲酰胺(4L)的溶液中添加氰化锌(II)(88.5g,753.6mmol)和四(三苯基膦)钯(65g,56.60mmol)。在100℃下搅拌反应混合物16小时。用甲苯稀释反应混合物且分离相。经甲苯萃取液相两次。再经盐水和氢氧化铵溶液洗涤有机相，用硫酸钠干燥并浓缩。残余物通过柱色谱法在硅胶上纯化(洗脱液：乙酸乙酯/环己烷1:5)，获得4-氰基-2-甲基苯甲酸甲酯(73g,89％产率)。1H NMR(400MHz,CDCl3):7.78(d,1H),7.52(m,2H),3.92(s,3H),2.62(s,3H)ppm.
实例I8:4-氰基-2-甲基苯甲酸
向4-氰基-2-甲基苯甲酸(实例I7)(61g,348mmol)在水(0.360ml)和四氢呋喃(1.4l)混合物的溶液中添加氢氧化锂水合物(31.4g,748.2mmol)。在环境温度下搅拌反应混合物3小时。再浓缩反应混合物。添加盐酸溶液(1N)进行酸化并通过甲醇和氯仿(5:95)的混合物进行萃取。用硫酸钠干燥有机相并浓缩。将残余物在乙酸乙酯和环己烷的混合物中结晶，获得4-氰基-2-甲基苯甲酸(55.5g,99％产率)。1H NMR(400MHz,CDCl3):7.89(d,1H),7.80(s,1H),7.72(d,1H),2.51(s,3H)ppm.
实例P1:N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基-苯基]-3- (4-氰基-2-甲基苯甲酰氨基)-2-甲氧基苯甲酰胺(表A中A5号化合物)
在氮气氛下，向4-溴-2-甲基苯甲酸(实例I8)(0.141g,0.8mmol)和N,N-二甲基甲酰胺(2滴)在二氯甲烷(5ml)的溶液中添加乙二酰氯(0.074ml,0.88mmol)。在环境温度下搅拌反应混合物1小时，然后在60℃下搅拌1.5小时。浓缩反应混合物并将残余物溶解于四氢呋喃(10ml)中。将该溶液逐滴地添加到3-氨基-N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基-丙基)-6-甲基苯基]-2-甲氧基苯甲酰胺(实例I5)(0.37g,0.73mmol)和吡啶(0.12ml,1.46mmol)在四氢呋喃(10ml)的溶液中。在环境温度下搅拌反应混合物16小时。将反应混合物倾倒进碳酸氢钠溶液(1M)中，并用乙酸乙酯萃取该混合物三次。用硫酸钠干燥有机相并浓缩。残余物通过柱色谱法在硅胶上纯化(洗脱液：乙酸乙酯/环己烷1:3)，获得表A中A5号化合物(0.240g,51％产率)。M.p.104-105℃.1H NMR(400MHz,CDCl3):8.68(d,1H),8.62(s,1H),8.01(s,1H),7.92(d,1H),7.66(m,3H),7.41(m,3H),4.00(s,3H),2.72(q,2H),2.62(s,3H),2.39(s,3H),1.25(t,3H)ppm.
通过同样的方法制得下列化合物：
N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基苯基]-3-(4-氟-2- 氯苯甲酰氨基)-2-甲氧基苯甲酰胺(表A中A3号化合物)
1H NMR(400MHz,CDCl3):8.76(m,2H),8.71(d,1H),7.98(m,1H),7.71(dd,1H),7.39(m,3H),7.27(dd,1H),7.18(m,1H),4.03(s,3H),2.73(q,2H),2.39(s,3H),1.25(t,3H)ppm.
N-[2-溴-6-氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)苯基]-3-(4-氟-2-氯苯 甲酰氨基)-2-甲氧基苯甲酰胺(表B中B2号化合物)
M.p.178-179℃.1H NMR(400MHz,CDCl3):9.12(bs,1H),8.79(bs,1H),8.73(d,1H),7.79-7.72(m,2H),7.84(s,1H),7.72(s,1H),7.38(t,1H),7.25(m,1H),7.17(m,1H),4.07(s,3H)ppm.
N-[2-溴-6-氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)苯基]-3-(4-氰基-2-甲 基苯甲酰氨基)-2-甲氧基苯甲酰胺(表B中B1号化合物)
M.p.109-110℃.1H NMR(400MHz,CDCl3):9.04(bs,1H),8.69(d,1H),8.10(s,1H),7.93(dd,1H),7.84(s,1H),7.72(s,1H),7.63(m,3H),7.40(t,1H),4.04(s,3H),2.61(s,3H)ppm.
N-[2,6-二氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)苯基]-3-(4-氟-2-氯苯甲 酰氨基)-2-甲氧基苯甲酰胺(表C中C1号化合物)
1H NMR(400MHz,CDCl3):9.12(bs,1H),8.79-8.72(m,2H),7.97(m,1H),7.91(dd,1H),7.68(s,2H),7.48(t,1H),7.25(m,1H),7.16(m,1H),4.04(s,3H)ppm.
N-[2,6-二氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)苯基]-3-(4-氰基-2-甲基 苯甲酰氨基)-2-甲氧基苯甲酰胺(表C中C2号化合物)
1H NMR(400MHz,CDCl3):8.99(bs,1H),8.70(d,1H),8.02(s,1H),7.92(dd,1H),7.68(s,2H),7.62(s,3H),7.40(t,1H),4.02(s,3H),2.60(s,3H)ppm.
除了直接用酰基氯，以及用三乙胺来替代吡啶之外，制备下列化合物的方法基本相同：
N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基苯基]-3-(4-氟苯甲 酰氨基)-2-甲氧基苯甲酰胺(表A中A1号化合物)
1H NMR(400MHz,CDCl3):8.68(s,1H),8.57(d,1H),8.30(s,1H),7.89(m,2H),7.80(dd,1H),7.30(m,3H),7.17(m,2H),3.94(s,3H),2.66(q,2H),2.32(s,3H),1.15(t,3H).
实例P2:N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基-苯基]-3- (4-氰基苯甲酰氨基)-2-甲氧基苯甲酰胺
(表A中A4号化合物)
向3-氨基-N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基-丙基)-6-甲基苯基]-2-甲氧基苯甲酰胺(实例I5)(30mg,0.06mmol)在四氢呋喃(1.2ml)的溶液中添加三乙胺(25μl,0.18mmol)。再添加4-氰基苯甲酸(17.6mg,0.12mmol)和双(2-氧代-3-恶唑烷基)膦酰氯(“BOP-Cl”)(30.4mg,0.12mmol)。将反应混合物加热回流6小时。冷却至环境温度并浓缩。将残余物溶解于二氯甲烷中并用盐酸溶液(1N)和碳酸氢钠水溶液(饱和的)洗涤。用硫酸钠干燥有机萃取物并浓缩。残余物通过柱色谱法在硅胶上纯化(洗脱液：环己烷/乙酸乙酯5:3)，获得表A中A4号化合物(35mg,93％产率)。1H NMR(400MHz,CDCl3):8.56(m,2H),8.48(bs,1H),7.97(m,2H),7.82(d,1H),7.78(d,2H),7.30(m,3H),3.94(s,3H),2.65(q,2H),2.30(s,3H),1.13(t,3H)ppm.
用同种方法制得下列化合物：
N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基苯基]-3-(2-甲基- 3-硝基苯甲酰氨基)-2-甲氧基苯甲酰胺(表A中A2号化合物)
1H NMR(400MHz,CDCl3):8.62(d,1H),8.53(s,1H),7.91(m,2H),7.86(d,1H),7.67(d,1H),7.42(t,1H),7.30(m,3H),3.91(s,3H),2.64(q,2H),2.59(s,3H),2.31(s,3H),1.14(t,3H)ppm.
实例P3:N-{3-[2-溴-6-氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-苯氨羰基]- 2-甲氧基苯基}-2,4,6-三氟苯甲酰胺
在氮气氛下，向2,4,6-三氟苯甲酸(8.114g,46.08mmol)和N,N二甲基甲酰胺(数滴)在二氯甲烷(50ml)的溶液中添加乙二酰氯(4.55mL,53.76mmol)。于环境温度下搅拌反应混合物1小时，然后于60℃下搅拌1.5小时。浓缩反应混合物，并将残余物溶解于四氢呋喃(200ml)。将该溶液逐滴地添加到3-氨基-N-[2-溴-6-氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)苯基]-2-甲氧基苯甲酰胺(实例I5)(22.03g,38.40mmol)和吡啶(6.18ml,76.80mmol)在四氢呋喃(200ml)的溶液中。在环境温度下搅拌反应混合物2小时。将反应混合物倾倒进碳酸氢钠溶液(1M)中，并用乙酸乙酯萃取该混合物三次。用硫酸钠干燥有机相并浓缩。残余物通过在硅胶上过滤纯化获得表B中B189号化合物(28.0g,99％产率)。M.p.179℃.1H NMR(400MHz,CDCl3):9.14(s,1H),8.72(d,1H),8.28(s,1H),7.97(q,1H),7.85(s,1H),7.74(s,1H),7.41(t,1H),6.88(t,1H),4.08(s,3H)ppm.
实例P4:经并行合成法从酸性氯化物中制备苯甲酰胺
对于表B中的B3号化合物，可通过将氨基衍生物(0.78mmol)，如3-氨基-N-[2-氯-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-溴苯基]-2-甲氧基苯甲酰胺(实例I5)，溶解于甲苯(15.6ml)来制备溶液A。对于表B中的B3号化合物，可通过将酸性氯化物(45μmol)，如2-氟苯甲酰氯，溶解于甲苯(0.36ml)来制备溶液B。将溶液A(0.6ml,30μmol)放入到一个反应井中，然后再相继将溶液B(0.36ml,45μmol)和二异丙基乙胺(“Hunig's Base”)(30μl,150μmol)加到该反应井中。在80℃下搅拌反应混合物16小时。蒸发掉溶剂并用乙腈(0.6ml)和N,N二甲基乙酰胺(0.2ml)的混合物将其稀释，然后用高性能液体色谱法将其纯化，获得所需的化合物。
这种方法用于并行合成多种化合物。
实例P5:经并行合成法从羧酸中制备苯甲酰胺
对于表A中的A9号化合物，可通过将氨基衍生物(0.65mmol)，如3-氨基-N-[2-乙基-4-(1,2,2,3,3,3-六氟-1-三氟甲基丙基)-6-甲基苯基]-2-甲氧基苯甲酰胺(实例I5)，溶解于N,N-二甲基乙酰胺(“DMA”)(9.6ml)来制备溶液A。对于表A中的A9号化合物，可通过将羧酸(37.5μmol)，如2-氯苯甲酸，溶解于N,N-二甲基乙酰胺(“DMA”)(0.38ml)来制备溶液B。可通过将(2-氧代-3-恶唑烷基)次磷酰氯(“BOP-Cl”)(1.95mmol)溶解于N,N-二甲基乙酰胺(“DMA”)(7.8ml)来制备溶液C。将溶液A(0.4ml,0.025mmol)放入到一个反应井中，然后再相继将溶液B(0.38ml,37.5μmol)，溶液C(0.2mL,50μmol)和二异丙基乙胺(“Hunig'sBase”)(40μl,200μmol)加到该反应井中。在100℃下搅拌反应混合物16小时。蒸发掉溶剂并用乙腈(0.6ml)和N,N二甲基乙酰胺(0.2ml)的混合物将其稀释，然后用高效液相色谱(HPLC)将其纯化，获得所需的化合物。
这种方法用于并行合成多种化合物。
通过下列HPLC-MS方法分析表A至L的化合物：
方法1:
方法2:
方法3:
方法4:
表A:
表B:
表C:
表D:
表E:
表F:
表G:
表H:
表I:
表J:
表K:
表L:
表M:
生物实施例
这些实施例阐明式(I)化合物的杀虫/杀昆虫的性质。进行了如下测试：
棉贪夜蛾(Spodoptera littoralis)(斜纹夜蛾)：
将棉花叶盘置于24-孔微量滴定板中的琼脂上并喷以200ppm施用量的测试溶液。干燥后，用5只L1幼虫侵染该叶盘。处理3天后(DAT)检测样品的死亡率、摄食行为和生长调节。
下列化合物对棉贪夜蛾(Spodoptera littoralis)的防除率在80％以上：A1到A22,B202到B207,B188,B187,B186,B185,B159,B158,B152,B151,B150,B166,B148,B147,B146,B144,B142,B141,B139,B138,B137,B135,B134,B131,B130,B128,B127,B126,B124,B120,B117,B116,B115,B114,B113,B112,B111,B110,B109,B105,B104,B102,B101,B100,B99,B98,B97,B96,B95,B94,B93,B92,B89,B88,B87,B86,B85,B84,B82,B81,B83,B80,B77,B74,B73,B72,B71,B70,B69,B68,B67,B66,B65,B64,B62,B61,B58,B56,B55,B54,B52,B48,B45,B44,B42,B39,B37,B36,B32,B31,B30,B28,B27,B26,B25,B175,B174,B176,B170,B169,B168,B167,B154,B172,B153,B180,B179,B178,B182,B184,B183,B156,B195,B194,B193,B155,B192,B191,B190,B189,B157,B198,B197,B196,B24,B23,B22,B21,B20,B19,B18,B17,B16,B15,B14,B13,B12,B11,B10,B9,B8,B7,B6,B5,B4,B3,B2,B1,C1到C15,C18到C23,C25到C36,D1到D13,D15,D17,D20,D23,D22,D26到D30,D32到D36,D39到D42,D44到D49,E1到E22,E24,E25到E29,F1到F9,F12,F13,F15到F30,G1到G5,K1到K4,M1,M2.
烟芽夜蛾(Heliothis virescens)(烟青虫)：
将卵(0-24时龄)置于24-孔微量滴定板中的人工食料上并通过移液用200ppm(在孔中浓度为18ppm)施用量的测试溶液处理。在4天的孵育期后，检查样品的卵死亡率、幼虫死亡率和生长调节。
下列化合物对烟芽夜蛾(Heliothis virescens)的防除率在80％以上：A1,A4,A6到A21,B202到B207,B188,B185,B163,B162,B161,B159,B158,B152,B151,B150,B166,B148,B146,B144,B141,B139,B138,B137,B135,B134,B131,B130,B128,B127,B126,B125,B124,B120,B117,B116,B115,B114,B113,B112,B111,B110,B109,B104,B102,B101,B100,B99,B98,B97,B96,B95,B94,B93,B89,B88,B87,B86,B85,B84,B82,B81,B83,B80,B77,B74,B73,B72,B70,B69,B68,B67,B66,B65,B64,B62,B61,B58,B56,B55,B52,B48,B45,B44,B42,B39,B36,B32,B31,B30,B27,B26,B25,B175,B174,B176,B171,B170,B169,B168,B167,B172,B153,B180,B179,B178,B182,B184,B183,B156,B195,B194,B193,B155,B192,B191,B190,B189,B157,B198,B197,B23,B22,B21,B20,B19,B18,B17,B15,B13,B12,B11,B10,B9,B8,B7,B6,B5,B4,B3,B2,B1,C1到C23,C25到C29,C31到C35,D1到D7,D10到D13,D15,D16,D20,D22到D24,D26,D28到D30,D32,D35,D36,D39到D42,D44到D49,E1到E24,E25到E29,F1到F9,F12,F13,F15到F30,G1到G5,H1,H2,H25,I1,I2,I25,J2到J4,J27,K1到K4,M1,M2.
小菜蛾(Plutella xylostella)(小菜蛾)：
通过移液用200ppm(在孔中浓度为18ppm)施用量的测试溶液处理具有人工食料的24-孔微量滴定板(MTP)。干燥后，将MTP用L2幼虫(7-12只每孔)侵染。在6天的孵育期后，检查样品的幼虫死亡率和生长调节。
下列化合物对小菜蛾(Plutella xylostella)的防除率在80％以上：A1,A2,A4到A22,B202到B207,B187,B185,B164,B163,B162,B161,B160,B159,B158,B152,B151,B150,B166,B148,B146,B144,B141,B139,B138,B137,B135,B134,B131,B130,B128,B127,B126,B125,B124,B120,B117,B116,B115,B114,B113,B112,B111,B110,B109,B105,B104,B102,B101,B100,B99,B98,B97,B96,B95,B94,B93,B89,B88,B87,B86,B85,B84,B82,B81,B83,B80,B77,B74,B73,B72,B71,B69,B67,B66,B65,B64,B62,B61,B58,B57,B56,B55,B54,B52,B48,B45,B44,B42,B39,B37,B36,B32,B31,B28,B27,B26,B25,B175,B174,B176,B171,B170,B169,B168,B154,B172,B153,B180,B179,B178,B182,B184,B183,B156,B195,B194,B193,B155,B192,B191,B190,B189,B198,B197,B196,B23,B22,B21,B20,B19,B18,B16,B15,B14,B13,B12,B11,B10,B9,B8,B7,B6,B5,B4,B3,B2,B1,C1到C9,C11到C13,C15,C18到C23,C25到C29,C31到C35,D1到D13,D15,D16,D20,D22到D24,D26到D30,D32,D36,D39到D42,D44到D49,E4到E22,E24,E25到E29,F1到F9,F11,F15到F27,F29,F30,G1到G5,H1,H2,H25,I1,I2,I25,J1到J4,J27,K1到K4,M1,M2.
巴西玉米根虫(Diabrotica balteata)(玉米根虫)：
通过移液用200ppm(在孔中浓度为18ppm)施用量的测试溶液处理具有人工食料的24-孔微量滴定板(MTP)。干燥后，将MTP用L2幼虫(6-10只每孔)侵染。在5天的孵育期后，检查样品的幼虫死亡率和生长调节。
下列化合物对巴西玉米根虫(Diabrotica balteata)的防除率在80％以上：A1,A3到A13,A15到A20,A22,B202到B206,B187,B185,B163,B162,B161,B159,B158,B151,B150,B166,B146,B144,B137,B135,B134,B131,B130,B128,B127,B126,B125,B120,B117,B116,B115,B113,B112,B111,B110,B109,B101,B100,B98,B97,B96,B93,B92,B89,B87,B86,B85,B84,B82,B81,B83,B80,B74,B73,B72,B69,B67,B66,B64,B62,B61,B58,B56,B55,B54,B52,B45,B44,B42,B37,B36,B32,B30,B28,B27,B26,B25,B174,B170,B169,B168,B167,B154,B153,B180,B179,B178,B181,B184,B183,B156,B194,B155,B192,B22,B21,B20,B18,B9,B5,B4,B3,C1到C13,D15,C19到C23,C25到C29,C31到C36,D1到D13,D15到D17,D20到D23,D26到D30,D32,D36,D39,D42,D41,D44到D49,E1到E7,E8,E9,E11,E13,E16到E22,E24,E25到E29,F1,F3,F7到F9,F12,F15到F23,F24到F30,G1到G5,H2,H25,I1,I2,I25,J1到J4,J27,K1到K4,M2.
棉蓟马(Thrips tabaci)(洋葱蓟马)：
将向日葵叶盘置于24-孔微量滴定板中的琼脂上并喷以200ppm施用量的测试溶液。干燥后，用混龄的蚜虫群侵染该叶盘。在7天的孵育期后，检测样品的死亡率。
下列化合物对棉蓟马(Thrips tabaci)的防除率在80％以上：A2到A13,A17到A20,A22,B202,B204,B163,B162,B161,B151,B150,B146,B137,B135,B134,B127,B124,B115,B113,B112,B111,B110,B109,B101,B97,B93,B92,B89,B87,B82,B81,B80,B74,B73,B67,B66,B65,B64,B58,B55,B54,B52,B49,B46,B45,B44,B42,B37,B36,B28,B27,B26,B25,B175,B174,B176,B169,B168,B167,B154,B172,B153,B180,B178,B184,B183,B156,B155,B192,B191,B190,B21,B20,B9,B4,B1,C1到C9,C11,C13,C15,C18,C19,C20到C23,C25,C26,C29,C31,C33,D1到D5,D9,D12,D15,D17,D20,D22,D23,D26到D30,D32到D36,D44到D49,E1到E7,E9,E11,E12,E13,E16到E22,E25,E27到E29,F3,F7,F8,F20,F21,F29,F30,H25,I2,I25,J27,K1,K2,M1.
二斑叶螨(Tetranychus urticae)(二斑叶螨)：
将豆叶盘置于24-孔微量滴定板中的琼脂上并喷以200ppm施用量的测试溶液。干燥后，用混龄的叶螨群侵染该叶盘。8天后，分别检测叶盘上卵、幼虫及成虫的死亡率。
下列化合物对二斑叶螨(Tetranychus urticae)的防除率在80％以上：A2到A7,A10,A11,A16到A18,A22,B202,B204,B159,B158,B151,B150,B139,B138,B135,B134,B128,B127,B113,B111,B110,B109,B106,B104,B101,B98,B97,B96,B93,B82,B81,B80,B74,B73,B69,B67,B66,B65,B64,B61,B55,B54,B42,B36,B28,B26,B174,B176,B171,B170,B169,B168,B154,B172,B153,B180,B179,B178,B184,B183,B156,B195,B194,B193,B155,B192,B191,B190,B189,B198,B197,B196,B23,B21,B19,B15,B13,B11,B9,B8,B7,B6,B5,B4,B2,B1,C2,C4到C9,C11,C12,C13,C15,C19到C23,C25,C26,C29,C33,D2到D6,D8,D11,D13,D20,D22,D32,D39,D44到D49,E4,E5,E7,E9,E12,E13,E17,E19,E20,E24,E25,E27到E29,F21,F18,F15,F7,F5,F1,F28,F27,F25,F24,F29,F30,G1到G5,J2,J27,K1到K4,M1.
桃蚜(Myzus persicae)(绿桃蚜)：
将向日葵叶盘置于24-孔微量滴定板中的琼脂上并喷以200ppm施用量的测试溶液。干燥后，用混龄的桃蚜群侵染该叶盘。在6天(DAT)的孵育期后，检测样品的死亡率。下列化合物对桃蚜(Myzus persicae)的防除率在80％以上：A3,A4,A10,A11,A13,A17,A18,A22,B204,B151,B150,B137,B124,B111,B106,B98,B93,B89,B82,B80,B66,B55,B54,B45,B44,B42,B37,B36,B28,B26,B174,B168,B153,B156,B155,B189,B19,B18,B15,B8,B7,B6,B5,B4,B2,C1,C4到C6,C8,C18,C19,D1到D4,D20,D21,D39,D45,D48,D49,E1,E2,E4到E6,E9,E11,E12,E13,E16,E17,E21,E25,E27到E29,F7,F30,G3,G4,G5,H1,H25,I2,I25,J27,K2,K27.

Claims (10)

1.一种式(I)的化合物：
其中
Q1是芳基或杂环基，每个可选地被1-5个相同或不同的R3取代基取代；
Q2选自：
2-乙基-6-甲基-4-(九氟丁-2-基)苯基，
2-溴-6-氯-4-(九氟丁-2-基)苯基，
2,6-二氯-4-(九氟丁-2-基)苯基，
2,6-二甲基-4-(九氟丁-2-基)苯基，
2-氯-6-甲氧基甲基-4-(九氟丁-2-基)苯基，和
2溴-6-甲氧基甲基-4-(九氟丁-2-基)苯基；
R1选自氢，C1-C8烷基，C1-C8烷基羰基，C1-C8烷氧基羰基和C1C4烷基-C(O)NH2；
R2选自氢，C1-C8烷基，C1-C8烷基羰基，C1-C8烷氧基羰基和C1C4烷基-C(O)NH2；和
R3选自氰基，硝基，卤素，羟基，乙酸基，C1-C4烷基，C1-C4卤代烷基，C1-C4烷氧基，C1-C4卤代烷氧基，C1-C4烷硫基，C1-C4氧烷基-C1-C4烷基，C1-C4氧烷基-C1-C4氧烷基，CN-C1-C4烷基，C1-C4烷基-C(O)O，C1-C4烷基-S(O)2,NH2，C1-C4烷基NH，(C1-C4烷基)2N，(C1-C4烷基O)2P(O)O，苯基以及含有1-3个独立选自氮，氧和硫的5-6元单环杂环基；
或一种农业上可接受的盐或其N-氧化物。
2.根据权利要求1所述的化合物，其中Q1选自苯基，联苯基和含有1,2或3个独立选自氮，氧和硫的5-6元单环杂芳基基团；每个可选地被1-5个相同或不同的R3取代基取代。
3.根据权利要求2所述的化合物，其中Q1选自苯基，联苯基，呋喃基，吡啶基，噻吩基，噻二唑基，恶唑基，异恶唑基，噻唑基，异噻唑基，吡唑基和嘧啶碱基；每个可选地被1-3个相同或不同的R3取代基取代。
4.根据权利要求1-3中任一项所述的化合物，其中R3选自氰基，硝基，氟，氯，溴，碘，羟基，乙酸基，甲基，乙基，异丙基，叔丁基，二氟甲基，三氟甲基，甲氧基，乙氧基，二氟甲氧基，三氟甲氧基，甲硫基，异丙硫基，3-乙氧基-正-丙基，甲氧基甲基，2-甲氧基乙氧基，CH2CN，C(O)OCH3，S(O)2CH3，NH2，N(CH3)2，OP(O)(CH2CH3)2，苯基，N-吡咯基，噻二唑基和吡啶基。
5.根据权利要求4所述的化合物，其中R3选自氰基，硝基，溴，氯，氟，甲基，乙基，三氟甲基，甲氧基和三氟甲氧基。
6.根据权利要求1-5中任一项所述的化合物，其中R1和R2均为氢。
7.根据权利要求1-6中任一项所述的化合物，其中Q2选自
2-乙基-6-甲基-4-(九氟-丁-2-基)苯基，
2-溴-6-氯-4-(九氟-丁-2-基)苯基和
2,6-二氯-4-(九氟-丁-2-基)苯基。
8.一种防除昆虫、蜱螨、线虫或软体动物的方法，其包括将杀昆虫、杀螨、杀线虫或杀软体动物有效量的如权利要求1-7中任一项定义的式(I)化合物施用至害虫、害虫所在地、或易受害虫侵染的植物。
9.一种杀昆虫的、杀螨的、杀线虫的和杀软体动物的组合物，其包含杀昆虫、杀螨、杀线虫的和杀软体动物有效量的如权利要求1-7中任一项定义的式(I)化合物以及一种农业上可接受的稀释剂或载体。
10.根据权利要求9所述的组合物，其进一步额外地包括一种或多种杀昆虫的、杀螨的、杀线虫的和杀软体动物的化合物。
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Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
UA112556C2 (uk) 2011-10-03 2016-09-26 Сінгента Партісіпейшнс Аг Інсектицидні похідні 2-метоксибензамідів
WO2013092942A1 (en) 2011-12-21 2013-06-27 Syngenta Participations Ag Use of aminobenzamide derivatives for controlling animal parasites
US20150336881A1 (en) * 2012-06-22 2015-11-26 Sumitomo Chemical Company, Limited Amide compound and use thereof for pest control
AU2013339584A1 (en) 2012-10-31 2015-04-09 Syngenta Participations Ag Insecticidal compounds
WO2014161850A1 (en) 2013-04-02 2014-10-09 Syngenta Participations Ag Process for the preparation of amides from hindered anilines containing a perhaloalkyl group
CN105102433B (zh) 2013-04-02 2017-12-15 先正达参股股份有限公司 杀虫化合物
JP6505080B2 (ja) * 2013-04-02 2019-04-24 シンジェンタ パーティシペーションズ アーゲー 殺虫性化合物
BR112016014774B1 (pt) * 2013-12-23 2021-08-10 Syngenta Participations Ag Compostos inseticidas
MX2017012646A (es) * 2015-04-17 2018-01-24 Dow Agrosciences Llc Moleculas que tienen utilidad plaguicida, e intermediarios, composiciones y procesos, relacionados con ellas.
US10647660B2 (en) * 2015-12-18 2020-05-12 Mitsui Chemicals Agro, Inc. Method of producing aromatic amide derivative
BR112019006746B8 (pt) * 2016-10-12 2022-09-06 Dow Agrosciences Llc Molécula apresentando utilidade pesticida, composição, e processos para controle de pragas
CA3099870C (en) 2018-05-11 2023-03-07 Shenyang University Of Chemical Technology Benzamide compound and use thereof
WO2020200290A1 (zh) * 2019-04-02 2020-10-08 沈阳化工大学 一种间二酰胺类化合物及其应用
AU2023219153A1 (en) * 2022-02-14 2024-06-06 Exxonmobil Chemical Patents Inc. Agricultural chemical formulation

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008000438A1 (en) * 2006-06-27 2008-01-03 Syngenta Participations Ag Insecticidal compounds

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU731777B2 (en) 1998-11-30 2001-04-05 Nihon Nohyaku Co., Ltd. Aniline derivative and process for producing the same
US8158814B2 (en) * 2003-08-29 2012-04-17 Mitsui Chemicals, Inc. Insecticide for agricultural or horticultural use and method of use thereof
CN101906053B (zh) 2004-01-28 2012-11-21 三井化学株式会社 酰胺衍生物
JP2006306771A (ja) 2005-04-28 2006-11-09 Mitsui Chemicals Inc 農園芸用殺虫剤
KR20090130887A (ko) 2005-06-21 2009-12-24 미쓰이 가가쿠 가부시키가이샤 아미드 유도체 및 이 화합물을 함유하는 살충제
BRPI0611697A2 (pt) 2005-06-23 2010-09-28 Mitsui Chemicals Inc derivado de amida, inseticida contendo o mesmo e método para aplicação do mesmo como inseticida
JP4580836B2 (ja) * 2005-07-25 2010-11-17 三井化学アグロ株式会社 殺虫殺菌組成物
JP2007031395A (ja) 2005-07-29 2007-02-08 Bayer Cropscience Ag 殺虫性３−アシルアミノベンズアニリド類
BRPI0719126B1 (pt) * 2006-12-21 2016-10-18 Syngenta Participations Ag composto, método para combater e controlar insetos, acarinos, nematódeos ou moluscos, e, composição inseticida, acaricida ou nematicida
GB0720320D0 (en) 2007-10-17 2007-11-28 Syngenta Participations Ag Insecticidal compounds
EP2072501A1 (en) * 2007-12-21 2009-06-24 Bayer CropScience AG Aminobenzamide derivatives as useful agents for controlling animal parasites
EP2319830B1 (en) * 2008-08-13 2016-11-02 Mitsui Chemicals Agro, Inc. Amide derivative, pest control agent containing the amide derivative, and use of the pest control agent

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008000438A1 (en) * 2006-06-27 2008-01-03 Syngenta Participations Ag Insecticidal compounds

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