TWI381805B - Anthranilamide insecticides - Google Patents

Anthranilamide insecticides Download PDF

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TWI381805B
TWI381805B TW095115833A TW95115833A TWI381805B TW I381805 B TWI381805 B TW I381805B TW 095115833 A TW095115833 A TW 095115833A TW 95115833 A TW95115833 A TW 95115833A TW I381805 B TWI381805 B TW I381805B
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group
compound
halogen
alkyl
chloro
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TW095115833A
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TW200721977A (en
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George Philip Lahm
Thomas Paul Selby
Thomas Martin Stevenson
Andrew Edmund Taggi
James Francis Bereznak
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Du Pont
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鄰胺苯甲醯胺殺蟲劑O-amine benzamide insecticide

本發明係關於適於農藝及非農藝用途之特定鄰胺苯甲醯胺，其N －氧化物、鹽及組合物，及其用於在農藝及非農藝環境中控制諸如節肢動物之無脊椎害蟲之方法。The present invention relates to specific o-amine benzamides suitable for agronomic and non-agronomic uses, N -oxides, salts and compositions thereof, and their use for controlling invertebrate pests such as arthropods in agronomic and non-agronomic environments The method.

為達成農作物生產之高效率，無脊椎害蟲之控制極其重要。無脊椎害蟲對於生長與儲存之農作物的危害可引起產量的顯著下降且因而導致消費者成本增加。在森林、溫室農作物、觀賞植物、苗圃農作物、儲存食物與纖維產品、牲畜、家庭、草坪、木產品及公共與動物衛生中無脊椎害蟲之控制亦重要。可購得多種產品用於此等目的，但仍需要更有效、更廉價、更小毒性、對環境更安全或具有不同作用模式之新穎化合物。In order to achieve high efficiency in crop production, the control of invertebrate pests is extremely important. The hazards of invertebrate pests to growing and storing crops can cause a significant drop in yield and thus lead to increased consumer costs. Control of invertebrate pests in forests, greenhouse crops, ornamental plants, nursery crops, stored food and fiber products, livestock, households, lawns, wood products and public and animal health is also important. A variety of products are commercially available for these purposes, but still require novel compounds that are more effective, less expensive, less toxic, safer to the environment, or have different modes of action.

PCT專利公開案WO 03/015518揭示式I之N －醯基鄰胺苯甲酸衍生物作為殺節肢動物劑： 其中，尤其A及B獨立為O或S；R1 為H、C1 －C6 烷基、C2 －C6 烷氧基羰基或C2 －C6 烷基羰基；R2 為H或C1 －C6 烷基；且R3 為H或視情況經取代的C1 －C6 烷基、C2 －C6 烯基、C2 －C6 炔基或C3 －C6 環烷基。PCT Patent Publication WO 03/015518 discloses N -mercapto-o-amine benzoic acid derivatives of formula I as arthropodicides: Wherein, in particular, A and B are independently O or S; R 1 is H, C 1 -C 6 alkyl, C 2 -C 6 alkoxycarbonyl or C 2 -C 6 alkylcarbonyl; R 2 is H or C 1 -C 6 alkyl; and R 3 is H or optionally substituted C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl .

本發明係針對式1 之化合物，包括其所有幾何及立體異構體、N －氧化物及農藝學或非農藝學鹽，含有其之農業及非農業組合物及其用於控制無脊椎害蟲之用途： 其中：J為視情況經1至4個獨立選自R5 之取代基取代的苯基；或J為選自由以下物質組成之群之雜環： R1 a 為C1 －C6 烷基、C2 －C6 烯基、C2 －C6 炔基、C3 －C6 環烷基、C1 －C6 鹵烷基、C2 －C6 鹵烯基、C2 －C6 鹵炔基、C3 －C6 鹵環烷基、鹵素、CN、CHO、NO2 、C1 －C4 烷氧基、C1 －C4 鹵烷氧基、C1 －C4 烷基硫基、C1 －C4 烷基亞磺醯基、C1 －C4 烷基磺醯基、C1 －C4 鹵烷基硫基、C1 －C4 鹵烷基亞磺醯基、C1 －C4 鹵烷基磺醯基、C2 －C4 烷基羰基、C2 －C4 烷氧基羰基、C2 －C4 烷基胺基羰基、C3 －C5 二烷基胺基羰基、C1 －C4 烷基胺基或C2 －C6 二烷基胺基；R1 b 為H、C1 －C6 烷基、C2 －C6 烯基、C2 －C6 炔基、C3 －C6 環烷基、C1 －C6 鹵烷基、C2 －C6 鹵烯基、C2 －C6 鹵炔基、C3 －C6 鹵環烷基、鹵素、CN、CHO、NO2 、C1 －C4 烷氧基、C1 －C4 鹵烷氧基、C1 －C4 烷基硫基、C1 －C4 烷基亞磺醯基、C1 －C4 烷基磺醯基、C1 －C4 鹵烷基硫基、C1 －C4 鹵烷基亞磺醯基、C1 －C4 鹵烷基磺醯基、C2 －C4 烷基羰基、C2 －C4 烷氧基羰基、C2 －C4 烷基胺基羰基、C3 －C5 二烷基胺基羰基、C1 －C4 烷基胺基或C2 －C6 二烷基胺基；R2 為H；或C1 －C6 烷基、C2 －C6 烯基、C2 －C6 炔基或C3 －C6 環烷基，各視情況經一或多個選自由鹵素、CN、NO2 、羥基、C1 －C4 烷基、C1 －C4 烷氧基、C1 －C4 烷基硫基、C1 －C4 烷基亞磺醯基、C1 －C4 烷基磺醯基、C2 －C4 烷氧基羰基、C1 －C4 烷基胺基、C2 －C8 二烷基胺基及C3 －C6 環烷基胺基組成之群之取代基取代；或R2 為C2 －C6 烷基羰基、C2 －C6 烷氧基羰基、C2 －C6 烷基胺基羰基或C3 －C8 二烷基胺基羰基；R3 為H、C1 －C6 烷基、C2 －C6 烯基、C2 －C6 炔基、C3 －C6 環烷基、C1 －C4 烷氧基、C1 －C4 烷基胺基、C2 －C8 二烷基胺基、C3 －C6 環烷基胺基、C2 －C6 烷氧基羰基或C2 －C6 烷基羰基；R4 為C4 －C1 2 烷基環烷基、C5 －C1 2 烯基環烷基、C5 －C1 2 炔基環烷基、C4 －C1 2 環烷基烷基、C5 －C1 2 環烷基烯基、C5 －C1 2 環烷基炔基、C4 －C1 2 環烯基烷基或C4 －C1 2 烷基環烯基，各視情況經1至6個選自CH3 及鹵素之取代基取代；或R4 為C3 －C5 環氧乙烷基烷基、C3 －C5 硫雜環丙烷基烷基、C4 －C6 環氧丙烷基烷基、C4 －C6 硫雜環丁烷基烷基、3－環氧丙烷基或3－硫雜環丁烷基，各視情況經1至5個獨立選自C1 －C3 烷基、C1 －C3 鹵烷基、鹵素、CN、C2 －C4 烷氧基羰基及C2 －C4 鹵烷氧基羰基之取代基取代；或R4 為C3 －C5 吖丙啶基烷基、C4 －C6 吖丁啶基烷基或3－吖丁啶基，經連接至氮原子之R1 0 取代，且視情況在碳原子上經1至5個獨立選自C1 －C3 烷基、C1 －C3 鹵烷基、鹵素、CN、C2 －C4 烷氧基羰基及C2 －C4 鹵烷氧基羰基之取代基取代；各R5 獨立為C1 －C6 烷基、C3 －C6 環烷基、C1 －C6 鹵烷基、鹵素、CN、C1 －C4 烷氧基、C1 －C4 烷基硫基、C1 －C4 鹵烷氧基、C1 －C4 鹵烷基硫基、C1 －C4 鹵烷基亞磺醯基或C1 －C4 鹵烷基磺醯基；或各R5 獨立為視情況經1至3個R9 取代之苯基或吡啶基；各R6 獨立選自由H、C1 －C6 烷基、C3 －C6 環烷基、C1 －C6 鹵烷基、鹵素、CN、C1 －C4 烷氧基、C2 －C4 烷氧基羰基、C1 －C4 烷基硫基、C1 －C4 鹵烷氧基、C1 －C4 鹵烷基硫基、C1 －C4 鹵烷基亞磺醯基及C1 －C4 鹵烷基磺醯基組成之群；R7 為視情況經一或多個選自由鹵素、CN、NO2 、羥基、C1 －C4 烷氧基、C1 －C4 烷基硫基、C1 －C4 烷基亞磺醯基、C1 －C4 烷基磺醯基、C2 －C4 烷氧基羰基、C1 －C4 烷基胺基、C2 －C8 二烷基胺基及C3 －C6 環烷基胺基組成之群之取代基取代的C1 －C6 烷基；或視情況經1至3個選自R9 之取代基取代的苯基；或R7 為 R8 為H、C1 －C6 烷基、C1 －C6 鹵烷基、C3 －C6 烯基、C3 －C6 鹵烯基、C3 －C6 炔基或C3 －C6 鹵炔基；各R9 獨立為C1 －C6 烷基、C3 －C6 環烷基、C1 －C6 鹵烷基、鹵素、CN、C1 －C4 烷氧基、C1 －C4 烷基硫基、C1 －C4 鹵烷氧基、C1 －C4 鹵烷基硫基、C1 －C4 鹵烷基亞磺醯基或C1 －C4 鹵烷基磺醯基；R1 0 為H、C1 －C3 烷基、C1 －C3 鹵烷基、C2 －C4 烷基羰基、C2 －C4 鹵烷基羰基、C2 －C4 烷氧基羰基或C1 －C3 烷基磺醯基；且s為0、1或2；其限制條件為：(i)式1 化合物不為N －[2－氯－6－[[(1－甲基環丙基)胺基]羰基]苯基]－1－(3－氯－2－吡啶基)－3－(三氟甲基)－1H －吡唑－5－甲醯胺；且(ii)式1 化合物不為3－溴－1－(3－氯－2－吡啶基)－N －[4－氰基－2－[[(環丙基甲基)胺基]羰基]－6－甲基苯基]－1H －吡唑－5－甲醯胺。The present invention is directed to a compound of formula 1 , including all geometric and stereoisomers thereof, N -oxides and agronomic or non-agronomic salts, agricultural and non-agricultural compositions containing the same, and their use for controlling invertebrate pests use: Wherein: J is a phenyl group optionally substituted with 1 to 4 substituents independently selected from R 5 ; or J is a heterocyclic ring selected from the group consisting of: R 1 a is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, CN, CHO, NO 2, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy , C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4- haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkoxycarbonyl, C 2 -C 4 alkylaminocarbonyl , C 3 -C 5 dialkylaminocarbonyl, C 1 -C 4 alkylamino or C 2 -C 6 dialkylamino; R 1 b is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, CN, CHO, NO 2 , C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 alkylsulfinyl -C 4 acyl, C 1 -C 4 alkylsulfonyl group, C 1 -C 4 haloalkyl thio, C 1 -C 4 alkylsulfinyl acyl halide , C 1 -C 4 alkylsulfonyl group halogen, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkoxycarbonyl, C 2 -C 4 alkyl aminocarbonyl, C 3 -C 5 dioxane Aminocarbonyl, C 1 -C 4 alkylamino or C 2 -C 6 dialkylamino; R 2 is H; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl, each optionally selected from halo, CN, NO 2 , hydroxy, C 1 -C 4 alkyl, C 1 -C 4 alkoxy , C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkoxycarbonyl, C 1 -C 4 alkane Substituted with a substituent of a group consisting of a C 2 -C 8 dialkylamino group and a C 3 -C 6 cycloalkylamine group; or R 2 is a C 2 -C 6 alkylcarbonyl group, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl or C 3 -C 8 dialkylaminocarbonyl; R 3 is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylamino, C 2 -C 8 dialkylamino, C 3 - C 6 cycloalkyl group, C 2 -C 6 alkoxycarbonyl or C 2 -C 6 alkylcarbonyl R 4 is C 4 -C 1 2 alkyl cycloalkyl, C 5 -C 1 2 alkenyl cycloalkyl, C 5 -C 1 2 alkynyl cycloalkyl, C 4 -C 1 2 cycloalkylalkyl , C 5 -C 1 2 alkenyl, cycloalkyl, C 5 -C 1 2 alkynyl cycloalkyl, C 4 -C 1 2 alkyl or cycloalkenyl C 4 -C 1 2 alkyl group cycloalkenyl group, each of Optionally substituted with 1 to 6 substituents selected from CH 3 and halogen; or R 4 is C 3 -C 5 oxiranylalkyl, C 3 -C 5 thicycloalkylalkyl, C 4 -C 6 propylene oxide alkyl, C 4 -C 6 thietane alkyl, 3-epoxypropane or 3-thietyl, each optionally selected from 1 to 5 Substituted from a substituent of a C 1 -C 3 alkyl group, a C 1 -C 3 haloalkyl group, a halogen, a CN, a C 2 -C 4 alkoxycarbonyl group, and a C 2 -C 4 haloalkoxycarbonyl group; or R 4 Is C 3 -C 5 aziridinylalkyl, C 4 -C 6 azetidinylalkyl or 3-azetidinyl, substituted by R 1 0 attached to a nitrogen atom, and optionally 1 to 5 on a carbon atom Substituent independently selected from C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, halogen, CN, C 2 -C 4 alkoxycarbonyl and C 2 -C 4 haloalkoxycarbonyl; Each R 5 is independent C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, halogen, CN, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl or C 1 -C 4 haloalkylsulfonyl; or each R 5 independent a phenyl or pyridyl group substituted by 1 to 3 R 9 as appropriate ; each R 6 is independently selected from H, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 halo Base, halogen, CN, C 1 -C 4 alkoxy, C 2 -C 4 alkoxycarbonyl, C 1 -C 4 alkylthio, C 1 -C 4 haloalkoxy, C 1 -C 4 a group consisting of a haloalkylthio group, a C 1 -C 4 haloalkylsulfinyl group, and a C 1 -C 4 haloalkylsulfonyl group; R 7 is optionally selected from the group consisting of halogen, CN, NO 2 , hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 - the group consisting of unsubstituted C 4 alkoxycarbonyl, C 1 -C 4 alkylamino, C 2 -C 8 dialkylamino and C 3 -C 6 cycloalkyl group substituted with a C 1 -C group 6 alkyl; or optionally substituted with 1 to 3 substituents selected from the substituent group R 9 Substituted phenyl; or R 7 is R 8 is H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl or C 3 - C 6 haloalkynyl; each R 9 is independently C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, halogen, CN, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl or C 1 -C 4 halo Alkylsulfonyl; R 1 0 is H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl, C 2 -C 4 alkoxycarbonyl or C 1 -C 3 alkylsulfonyl; and s is 0, 1 or 2; the limitation is that: (i) the compound of formula 1 is not N- [2-chloro-6- [[(1-Methylcyclopropyl)amino]carbonyl]phenyl]-1-(3-chloro-2-pyridyl)-3-(trifluoromethyl)-1 H -pyrazole-5- a Amides; and compound (ii) formula 1 is not 3-bromo-1- (3-chloro-2-pyridinyl) - N - [4- cyano-2 - [[(cyclopropylmethyl) amine Alkyl]carbonyl]-6-methylphenyl]-1 H -pyrazole-5-formamide.

本發明亦提供一種包含式1 化合物及至少一種選自由界面活性劑、固體稀釋劑及液體稀釋劑組成之群的額外組份之組合物，該組合物視情況另外包含至少一種額外之生物活性化合物或藥劑。The invention also provides a composition comprising a compound of formula 1 and at least one additional component selected from the group consisting of surfactants, solid diluents, and liquid diluents, optionally comprising at least one additional biologically active compound Or pharmacy.

本發明亦提供一種用於控制無脊椎害蟲之組合物，其包含生物有效量之式1 化合物及至少一種選自由界面活性劑、固體稀釋劑及液體稀釋劑組成之群的額外組份，該組合物視情況另外包含生物有效量之至少一種額外之生物活性化合物或藥劑。The invention also provides a composition for controlling an invertebrate pest comprising a biologically effective amount of a compound of formula 1 and at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, the combination The subject matter additionally comprises a biologically effective amount of at least one additional biologically active compound or agent.

本發明另外提供一種用於控制無脊椎害蟲之噴霧組合物，其包含生物有效量之式1 化合物或上述組合物及推進劑。本發明亦提供一種用於控制無脊椎害蟲之誘餌組合物，其包含生物有效量之式1 化合物或上述組合物、一或多種食物材料、視情況之引誘劑及視情況之保濕劑。The invention further provides a spray composition for controlling an invertebrate pest comprising a biologically effective amount of a compound of formula 1 or a composition as described above and a propellant. The present invention also provides a bait composition for controlling an invertebrate pest comprising a biologically effective amount of a compound of formula 1 or a composition as described above, one or more food materials, optionally an attractant, and optionally a humectant.

本發明另外提供一種用於控制無脊椎害蟲之捕獲裝置，其包含該誘餌組合物與適合容納該誘餌組合物之外殼，其中該外殼具有至少一開口，其尺寸允許無脊椎害蟲穿過該開口從而該無脊椎害蟲可自外殼外之位置得以接近該誘餌組合物，且其中該外殼另外適合置放於或靠近潛在或已知的無脊椎害蟲活躍地點。The present invention further provides a capture device for controlling an invertebrate pest comprising the bait composition and an outer casing adapted to receive the bait composition, wherein the outer casing has at least one opening sized to allow an invertebrate pest to pass through the opening The invertebrate pest can be accessed from the location outside the outer casing, and wherein the outer casing is otherwise adapted to be placed at or near an active or known active location of the invertebrate pest.

本發明亦提供一種用於控制無脊椎害蟲之方法，其包含使該無脊椎害蟲或其環境與生物有效量之式1 化合物(例如以本文所述組合物之形式)接觸。本發明亦係關於其中使該無脊椎害蟲或其環境與包含生物有效量之式1 化合物及至少一種選自由界面活性劑、固體稀釋劑及液體稀釋劑組成之群的額外組份之組合物接觸之該方法，該組合物視情況另外包含生物有效量之至少一種額外之生物活性化合物或藥劑。The invention also provides a method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of formula 1 (e.g., in the form of a composition described herein). The invention is also directed to contacting the invertebrate pest or its environment with a composition comprising a biologically effective amount of a compound of formula 1 and at least one additional component selected from the group consisting of surfactants, solid diluents, and liquid diluents. In this method, the composition additionally comprises a biologically effective amount of at least one additional biologically active compound or agent, as appropriate.

本發明亦係關於式10 之醯胺： 其中R1 a 、R1 b 、R2 、R3 及R4 係如針對式1 所定義，其可用作製備式1 化合物之中間物。The invention also relates to the indoleamine of formula 10 : Wherein R 1 a , R 1 b , R 2 , R 3 and R 4 are as defined for formula 1 and are useful as intermediates in the preparation of compounds of formula 1 .

如本文所用之術語"包含"、"包括"、"具有"、"含有"或其任何變體意欲覆蓋不排外之包括。例如，包含一系列要素之組合物、混合物、製程、方法、物件或設備不必僅限於此等要素，而可包括其他未明顯列出或固有的組合物、混合物、製程、方法、物件或設備之要素。另外，除非陳述明顯相反，"或"係指包括之"或"且非排他性之"或"。例如，條件A或B滿足於下列任何一情況：A正確(或存在)且B錯誤(或不存在)，A錯誤(或不存在)且B正確(或存在)及A與B皆正確(或存在)。The terms "comprising," "comprising," "having," "having," For example, a composition, mixture, process, method, article, or device that comprises a plurality of elements is not necessarily limited to such elements, but may include other compositions, mixtures, processes, methods, articles, or devices that are not explicitly listed or inherent. Elements. In addition, unless expressly stated to the contrary, "or" is meant to include the "or" and the non-exclusive "or". For example, condition A or B is satisfied in any of the following cases: A is correct (or exists) and B is wrong (or does not exist), A is wrong (or does not exist) and B is correct (or exists) and both A and B are correct (or presence).

同樣，在本發明之元素或組份前之不定冠詞"一"意欲關於元素或組份之實例(例如存在)之數目為非限制性的。因此應認為"一"包括一個或至少一個，且除非該數目明顯意謂單數，否則元素或組份之單數形式亦包括複數形式。Also, the indefinite article "a" or "an" or "an" The singular forms "a" or "an"

在以上敍述中，單獨使用或以諸如"烷基硫基"或"鹵烷基"之複合詞使用之術語"烷基"包括直鏈或支鏈烷基，例如甲基、乙基、正丙基、異丙基或不同的丁基、戊基或己基異構體。"烯基"包括直鏈或支鏈烯烴，例如乙烯基、1－丙烯基、2－丙烯基及不同的丁烯基、戊烯基及己烯基異構體。"烯基"亦包括諸如1,2－丙二烯基及2,4－己二烯基之多烯。"炔基"包括直鏈或支鏈炔烴，例如乙炔基、1－丙炔基、2－丙炔基及不同的丁炔基、戊炔基及己炔基異構體。"炔基"亦可包括包含多個三鍵之部分，例如2,5－己二炔。In the above description, the term "alkyl" used alone or in combination with a compound such as "alkylthio" or "haloalkyl" includes straight-chain or branched alkyl groups such as methyl, ethyl, n-propyl. , isopropyl or a different butyl, pentyl or hexyl isomer. "Alkenyl" includes straight-chain or branched olefins such as ethenyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers. "Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. "Alkynyl" includes straight-chain or branched alkyne such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. "Alkynyl" may also include moieties comprising a plurality of triple bonds, such as 2,5-hexadiyne.

"烷氧基"包括(例如)甲氧基、乙氧基、正丙氧基、異丙氧基及不同的丁氧基、戊氧基及己氧基異構體。"烷基硫基"包括支鏈或直鏈烷基硫基部分，例如甲基硫基、乙基硫基及不同的丙基硫基、丁基硫基、戊基硫基及己基硫基異構體。"烷基亞磺醯基"包括烷基亞磺醯基的兩種鏡像異構體。"烷基亞磺醯基"之實例包括CH3 S(O)－、CH3 CH2 S(O)－、CH3 CH2 CH2 S(O)－、(CH3 )2 CHS(O)－及不同的丁基亞磺醯基、戊基亞磺醯基及己基亞磺醯基異構體。"烷基磺醯基"之實例包括CH3 S(O)2 －、CH3 CH2 S(O)2 －、CH3 CH2 CH2 S(O)2 －、(CH3 )2 CHS(O)2 －及不同的丁基磺醯基、戊基磺醯基及己基磺醯基異構體。"烷基胺基"、"二烷基胺基"及其類似基團類似於以上實例定義。"環烷基"包括(例如)環丙基、環丁基、環戊基及環己基。術語"環烷基胺基"包括經由氮原子連接之相同基團，例如環戊基胺基及環己基胺基。術語"(烷基)環烷基胺基"表示鍵結至氮原子之支鏈或直鏈烷基及另外之環烷基，例如甲基環戊基胺基及乙基環己基胺基。"Alkoxy" includes, for example, methoxy, ethoxy, n-propoxy, isopropoxy and the different butoxy, pentyloxy and hexyloxy isomers. "Alkylthio" includes branched or straight chain alkylthio moieties such as methylthio, ethylthio and different propylthio, butylthio, pentylthio and hexylthio Structure. "Alkylsulfinyl" includes two mirror image isomers of an alkylsulfinyl group. Examples of "alkylsulfinyl" include CH 3 S(O)-, CH 3 CH 2 S(O)-, CH 3 CH 2 CH 2 S(O)-, (CH 3 ) 2 CHS(O) - and different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers. Examples of "alkylsulfonyl" include CH 3 S(O) 2 -, CH 3 CH 2 S(O) 2 -, CH 3 CH 2 CH 2 S(O) 2 -, (CH 3 ) 2 CHS ( O) 2 - and different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. "Alkylamino", "dialkylamino" and the like are defined analogously to the above examples. "Cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term "cycloalkylamino" includes the same groups attached through a nitrogen atom, such as cyclopentylamino and cyclohexylamino. The term "(alkyl)cycloalkylamino" denotes a branched or straight-chain alkyl group bonded to a nitrogen atom and another cycloalkyl group such as methylcyclopentylamino and ethylcyclohexylamino.

術語"烷基環烷基"表示環烷基部分上之烷基取代且包括(例如)乙基環丙基、異丙基環丁基、3－甲基環戊基及4－甲基環己基。"烯基環烷基"、"炔基環烷基"及其類似基團類似於以上實例定義。術語"環烷基烷基"表在烷基部分上之環烷基取代。"環烷基烷基"之實例包括環丙基甲基、環戊基乙基，及鍵結至直鏈或支鏈烷基上之其他環烷基部分。"環烷基烯基"、"環烷基炔基"及其類似基團類似於以上實例定義。"環烯基"包括諸如環戊烯基及環己烯基之基團以及諸如1,3－及1,4－環己二烯基之具有一個以上雙鍵之基團。術語"環烯基烷基"表示烷基部分上之環烯基取代且包括(例如)環戊烯基甲基及1－環己烯基乙基。術語"烷基環烯基"表示環烯基部分上之烷基取代且包括(例如)甲基環戊烯基及5－乙基－3－環己烯基。The term "alkylcycloalkyl" denotes an alkyl group substituted on the cycloalkyl moiety and includes, for example, ethylcyclopropyl, isopropylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. . "Alkenylcycloalkyl", "alkynylcycloalkyl" and the like are defined analogously to the above examples. The term "cycloalkylalkyl" is substituted by a cycloalkyl group on the alkyl moiety. Examples of "cycloalkylalkyl" include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to a straight or branched alkyl group. "Cycloalkylalkenyl", "cycloalkylalkynyl" and the like are defined analogously to the above examples. "Cycloalkenyl" includes groups such as cyclopentenyl and cyclohexenyl, and groups having one or more double bonds such as 1,3- and 1,4-cyclohexadienyl. The term "cycloalkenylalkyl" denotes a cycloalkenyl group on the alkyl moiety and includes, for example, cyclopentenylmethyl and 1-cyclohexenylethyl. The term "alkylcycloalkenyl" denotes an alkyl group substituted on the cycloalkenyl moiety and includes, for example, methylcyclopentenyl and 5-ethyl-3-cyclohexenyl.

術語"芳環系統"表示其中多環系統為芳族(其中芳族指示對於該環系統而言滿足休克爾(Hckel)規則)之完全不飽和碳環及雜環。與芳環基團有關之術語"視情況經取代"係指未經取代或具有至少一個非氫取代基之基團。通常，視情況取代基(若存在)之數目在1至4範圍內。The term "aromatic ring system" means wherein the polycyclic system is aromatic (where the aromatic indicates that the Heckel is satisfied for the ring system (H) Ckel) rules) fully unsaturated carbocyclic rings and heterocyclic rings. The term "optionally substituted" in relation to an aromatic ring group refers to a group which is unsubstituted or has at least one non-hydrogen substituent. Typically, the number of substituents, if any, is optionally in the range of 1 to 4.

單獨使用或以諸如"鹵烷基"之複合詞使用之術語"鹵素"包括氟、氯、溴或碘。此外，當用於諸如"鹵烷基"之複合詞中時，該烷基可部分或完全經可相同或不同的鹵原子取代。"鹵烷基"之實例包括F3 C－、ClCH2 －、CF3 CH2 －及CF3 CCl2 －。術語"鹵烯基"、"鹵炔基"、"鹵環烷基"、"鹵烷氧基"、"鹵烷基硫基"及其類似基團類似於術語"鹵烷基"定義。"鹵烯基"之實例包括(Cl)2 C＝CHCH2 －及CF3 CH2 CH＝CHCH2 －。"鹵炔基"之實例包括HC≡CCHCl－、CF3 C≡C－、CCl3 C≡C－及FCH2 C≡CCH2 －。"鹵烷氧基"之實例包括CF3 O－、CCl3 CH2 O－、HCF2 CH2 CH2 O－及CF3 CH2 O－。"鹵烷基硫基"之實例包括CCl3 S－、CF3 S－、CCl3 CH2 S－及ClCH2 CH2 CH2 S－。"鹵烷基亞磺醯基"之實例包括CF3 S(O)－、CCl3 S(O)－、CF3 CH2 S(O)－及CF3 CF2 S(O)－。"鹵烷基磺醯基"之實例包括CF3 S(O)2 －、CCl3 S(O)2 －、CF3 CH2 S(O)2 －及CF3 CF2 S(O)2 －。The term "halogen" used alone or in conjunction with a compound such as "haloalkyl" includes fluoro, chloro, bromo or iodo. Further, when used in a compound such as "haloalkyl", the alkyl group may be partially or completely substituted with the same or different halogen atoms. Examples of "haloalkyl" include F 3 C-, ClCH 2 -, CF 3 CH 2 -, and CF 3 CCl 2 -. The terms "haloalkenyl", "haloalkynyl", "halocycloalkyl", "haloalkoxy", "haloalkylthio" and the like are analogous to the term "haloalkyl". Examples of "haloalkenyl" include (Cl) 2 C=CHCH 2 - and CF 3 CH 2 CH=CHCH 2 -. Examples of "haloalkynyl" include HC≡CCHCl-, CF 3 C≡C-, CCl 3 C≡C-, and FCH 2 C≡CCH 2 -. Examples of "haloalkoxy" include CF 3 O-, CCl 3 CH 2 O-, HCF 2 CH 2 CH 2 O-, and CF 3 CH 2 O-. Examples of "haloalkylthio" include CCl 3 S-, CF 3 S-, CCl 3 CH 2 S-, and ClCH 2 CH 2 CH 2 S-. Examples of "haloalkylsulfinyl" include CF 3 S(O)-, CCl 3 S(O)-, CF 3 CH 2 S(O)-, and CF 3 CF 2 S(O)-. Examples of "haloalkylsulfonyl" include CF 3 S(O) 2 -, CCl 3 S(O) 2 -, CF 3 CH 2 S(O) 2 - and CF 3 CF 2 S(O) 2 - .

"烷基羰基"表示鍵結至C(＝O)部分之直鏈或支鏈烷基部分。"烷基羰基"之實例包括CH3 C(＝O)－、CH3 CH2 CH2 C(＝O)－及(CH3 )2 CHC(＝O)－。"烷氧基羰基"之實例包括CH3 OC(＝O)－、CH3 CH2 OC(＝O)、CH3 CH2 CH2 OC(＝O)－、(CH3 )2 CHOC(＝O)－及不同的丁氧基－或戊氧基羰基異構體。"烷基胺基羰基"之實例包括CH3 NHC(＝O)－、CH3 CH2 NHC(＝O)－、CH3 CH2 CH2 NHC(＝O)－、(CH3 )2 CHNHC(＝O)－及不同的丁基胺基－或戊基胺基羰基異構體。"二烷基胺基羰基"之實例包括(CH3 )2 NC(＝O)－、(CH3 CH2 )2 NC(＝O)－、CH3 CH2 (CH3 )NC(＝O)－、(CH3 )2 CHN(CH3 )C(＝O)－及CH3 CH2 CH2 (CH3 )NC(＝O)－。"Alkylcarbonyl" means a straight or branched alkyl moiety bonded to the C(=O) moiety. Examples of "alkylcarbonyl" include CH 3 C(=O)-, CH 3 CH 2 CH 2 C(=O)-, and (CH 3 ) 2 CHC(=O)-. Examples of "alkoxycarbonyl" include CH 3 OC(=O)-, CH 3 CH 2 OC(=O), CH 3 CH 2 CH 2 OC(=O)-, (CH 3 ) 2 CHOC(=O )- and different butoxy- or pentoxycarbonyl isomers. Examples of "alkylaminocarbonyl" include CH 3 NHC(=O)-, CH 3 CH 2 NHC(=O)-, CH 3 CH 2 CH 2 NHC(=O)-, (CH 3 ) 2 CHNHC ( =O)- and different butylamino- or pentylaminocarbonyl isomers. Examples of "dialkylaminocarbonyl" include (CH 3 ) 2 NC(=O)-, (CH 3 CH 2 ) 2 NC(=O)-, CH 3 CH 2 (CH 3 )NC(=O) -, (CH 3 ) 2 CHN(CH 3 )C(=O)- and CH 3 CH 2 CH 2 (CH 3 )NC(=O)-.

"三烷基矽烷基"包括連接至矽原子及經由矽原子連接的三個支鏈及/或直鏈烷基，例如三甲基矽烷基、三乙基矽烷基及第三丁基二甲基矽烷基。"Trialkylalkylalkyl" includes three branched and/or straight-chain alkyl groups attached to a ruthenium atom and attached via a ruthenium atom, such as trimethyl decyl, triethyl decyl, and tert-butyl dimethyl矽alkyl.

在取代基中碳原子總數目由前綴"Ci －Cj "指示，其中i及j為2至8的數字。舉例而言，C1 －C4 烷基磺醯基表示甲基磺醯基至丁基磺醯基；C2 烷氧基烷基表示CH3 OCH2 ；C3 烷氧基烷基表示(例如)CH3 CH(OCH3 )、CH3 OCH2 CH2 或CH3 CH2 OCH2 ；且C4 烷氧基烷基表示含有總共四個碳原子的經烷氧基取代之烷基的各種異構體，實例包括CH3 CH2 CH2 OCH2 及CH3 CH2 OCH2 CH2 。The total number of carbon atoms in the substituent is indicated by the prefix "C i -C j ", where i and j are numbers from 2 to 8. For example, C 1 -C 4 alkylsulfonyl refers to methylsulfonyl to butylsulfonyl; C 2 alkoxyalkyl denotes CH 3 OCH 2 ; C 3 alkoxyalkyl represents (eg CH 3 CH(OCH 3 ), CH 3 OCH 2 CH 2 or CH 3 CH 2 OCH 2 ; and C 4 alkoxyalkyl represents a variety of alkoxy-substituted alkyl groups containing a total of four carbon atoms Constructs, examples include CH 3 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .

當化合物經取代基取代且取代基帶有指示該等取代基之數目可超過1之下標時，該等取代基(當其超過1時)各自獨立選自由所定義取代基組成之群，例如(R9 )s ，s為0、1或2。當基團含有可為氫之取代基，例如R2 或R9 時，則當將此取代基視為氫時，認為此等價於該基團未經取代。When a compound is substituted with a substituent and the substituent bears a number indicating that the number of such substituents may exceed 1 or less, the substituents (when it exceeds 1) are each independently selected from the group consisting of the substituents defined, for example ( R 9 ) s , s is 0, 1 or 2. When a group contains a substituent which may be hydrogen, such as R 2 or R 9 , then when the substituent is considered to be hydrogen, it is considered equivalent to the group being unsubstituted.

本發明之化合物可以一或多種立體異構體之形式存在。各種立體異構體包括鏡像異構體、非鏡像異構體、滯轉異構體及幾何異構體。熟習此項技術者將瞭解當一種立體異構體相對於其他立體異構體富集時或當與其他立體異構體分離時可更具活性且/或展示有益作用。另外，熟習此項技術者瞭解如何分離、富集且/或選擇性製備該等立體異構體。因此，本發明包含選自式1 、其N －氧化物及農藝學及非農藝學適當鹽之化合物。本發明之化合物可以立體異構體之混合物、個別立體異構體之形式或以光學活性形式存在。The compounds of the invention may exist in the form of one or more stereoisomers. The various stereoisomers include the mirror image isomers, the non-image isomers, the stagnation isomers, and the geometric isomers. Those skilled in the art will appreciate that one stereoisomer may be more active and/or exhibit a beneficial effect when enriched relative to other stereoisomers or when separated from other stereoisomers. Additionally, those skilled in the art will understand how to isolate, enrich, and/or selectively prepare such stereoisomers. Accordingly, the present invention comprises a compound selected from the group consisting of Formula 1 , its N -oxides, and agrochemical and non-agronomically suitable salts. The compounds of the invention may exist as mixtures of stereoisomers, as individual stereoisomers or in optically active forms.

熟習此項技術者將瞭解並非所有含氮雜環皆可形成N －氧化物，因為氮需要可用的孤電子對用於氧化形成氧化物；熟習此項技術者可認別可形成N －氧化物之彼等含氮雜環。熟習此項技術者同樣可認識到三級胺可形成N －氧化物。熟習此項技術者非常熟知製備雜環及三級胺之N －氧化物之合成方法，包括以諸如過氧乙酸及間氯過苯甲酸(MCPBA)之過氧酸、過氧化氫、諸如氫過氧化第三丁基之氫過氧化烷基、過硼酸鈉及諸如二甲基二環氧乙烷之二環氧乙烷來氧化雜環及三級胺。製備N －氧化物之此等方法詳盡描述及綜述於文獻中，例如參見：T.L.Gilchrist在S.V.Ley，編輯，Pergamon press之Comprehensive Organic Synthesis ，第7卷，第748－750頁中；M.Tisler及B.Stanovnik在A.J.Boulton及A.McKillop編輯，Pergamon press之Comprehensive Heterocyclic Chemistry，第 3卷，第18－20頁中；M.R.Grimmett及B.R.T.Keene在A.R.Katritzky編輯，Academic Press之Advances in Heterocyclic Chemistry，第 43卷，第149－161頁中；M.Tisler及B.Stanovnik在A.R.Katritzky及A.J.Boulton編輯，Academic Press之Advances in Heterocyclic Chemistry，第 9卷，第285－291頁中；及G.W.H.Cheeseman及E.S.G.Werstiuk在A.R.Katritzky及A.J.Boulton編輯，Academic Press之Advances in Heterocyclic Chemistry，第 22卷，第390－392頁中。Those skilled in the art will appreciate that not all nitrogen-containing heterocycles can form N -oxides because nitrogen requires the use of a lone pair of electrons for oxidation to form oxides; those skilled in the art will recognize N -oxides. They are nitrogen-containing heterocycles. Those skilled in the art will also recognize that tertiary amines can form N -oxides. Methods of synthesizing N -oxides for the preparation of heterocyclic and tertiary amines, including peroxyacids such as peroxyacetic acid and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, such as hydrogen, are well known to those skilled in the art. The tertiary butyl hydroperoxyalkyl group, sodium perborate, and diethylene oxide such as dimethyldioxirane are oxidized to oxidize the heterocyclic ring and the tertiary amine. These methods for the preparation of N -oxides are described and reviewed in detail in the literature, see, for example, TLGilchrist, SVLey, ed., Pergamon Press, Comprehensive Organic Synthesis , Vol. 7, pp. 748-750; M. Tisler and B. Stanovnik, edited by AJ Boulton and A. McKillop, Pergamon press, Comprehensive Heterocyclic Chemistry, Vol. 3, pp. 18-20; MRGrimmett and BRT Keene, edited by ARKatritzky, Academic Press, Advances in Heterocyclic Chemistry, Vol. 43, pp. 149-161 Page; M. Tisler and B. Stanovnik, edited by ARKatritzky and AJ Boulton, Advances in Heterocyclic Chemistry , Academic Press , Vol. 9, pp. 285-291; and GWH Cheeseman and ESGWerstiuk, edited by ARKatritzky and AJ Boulton, Advances in Academic Press Heterocyclic Chemistry, Vol. 22, pp. 390-392.

本發明化合物之鹽包括與無機或有機酸之酸加成鹽，該等酸例如氫溴酸、鹽酸、硝酸、磷酸、硫酸、乙酸、丁酸、反丁烯二酸、乳酸、順丁烯二酸、丙二酸、草酸、丙酸、水楊酸、酒石酸、4－甲苯磺酸或戊酸。本發明化合物之鹽亦包括當該化合物含有諸如羧酸或酚之酸性基團時其與有機鹼(例如吡啶、氨或三乙胺)或無機鹼(例如鈉、鉀、鋰、鈣、鎂或鋇之氫化物、氫氧化物或碳酸鹽)形成的鹽。Salts of the compounds of the invention include acid addition salts with inorganic or organic acids such as hydrobromic acid, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, acetic acid, butyric acid, fumaric acid, lactic acid, butylene Acid, malonic acid, oxalic acid, propionic acid, salicylic acid, tartaric acid, 4-toluenesulfonic acid or valeric acid. The salt of the compound of the present invention also includes an organic base (for example, pyridine, ammonia or triethylamine) or an inorganic base (for example, sodium, potassium, lithium, calcium, magnesium or the like when the compound contains an acidic group such as a carboxylic acid or a phenol. a salt formed from a hydride, hydroxide or carbonate of hydrazine.

如發明內容中所描述本發明之實施例包括：實施例1A式1 之化合物，其中R1 a 為C1 －C4 烷基、C1 －C4 鹵烷基、鹵素、CN、NO2 、C1 －C4 烷氧基、C1 －C4 鹵烷氧基、C1 －C4 烷基硫基、C1 －C4 烷基亞磺醯基、C1 －C4 烷基磺醯基、C1 －C4 鹵烷基硫基、C1 －C4 鹵烷基亞磺醯基或C1 －C4 鹵烷基磺醯基。SUMMARY The embodiments of the present invention in the described invention include: the compound of Example 1 of the embodiment of Formula 1A, wherein R 1 a is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halo, CN, NO 2, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl a C 1 -C 4 haloalkylthio group, a C 1 -C 4 haloalkylsulfinyl group or a C 1 -C 4 haloalkylsulfonyl group.

實施例1B式1 之化合物，其中R1 a 為CH3 、CF3 、OCF3 、OCHF2 、S(O)n CF3 、S(O)n CHF2 、CN或鹵素；且n為0、1或2。Embodiment 1B Compound of Formula 1 , wherein R 1 a is CH 3 , CF 3 , OCF 3 , OCHF 2 , S(O) n CF 3 , S(O) n CHF 2 , CN or halogen; and n is 0, 1 or 2.

實施例1C式1 之化合物，其中R1 a 為CH3 、F、Cl、Br或I。Embodiment 1C A compound of Formula 1 wherein R 1 a is CH 3 , F, Cl, Br or I.

實施例1D式1 之化合物，其中R1 a 為CH3 、Cl、Br或I。Embodiment 1D A compound of Formula 1 wherein R 1 a is CH 3 , Cl, Br or I.

實施例1E式1 之化合物，其中R1 a 為CH3 或Cl。Embodiment 1E A compound of Formula 1 wherein R 1 a is CH 3 or Cl.

實施例2A式1 之化合物，其中R1 b 為 H、C1 －C4 烷基、C1 －C4 鹵烷基、鹵素、CN、NO2 、C1 －C4 烷氧基、C1 －C4 鹵烷氧基、C1 －C4 烷基硫基、C1 －C4 烷基亞磺醯基、C1 －C4 烷基磺醯基、C1 －C4 鹵烷基硫基、C1 －C4 鹵烷基亞磺醯基或C1 －C4 鹵烷基磺醯基。Embodiment 2A A compound of Formula 1 , wherein R 1 b is H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halogen, CN, NO 2 , C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkyl sulfide a C 1 -C 4 haloalkylsulfinyl group or a C 1 -C 4 haloalkylsulfonyl group.

實施例2B式1 之化合物，其中R1 b 為H、CH3 、CF3 、OCF3 、OCHF2 、S(O)p CF3 、S(O)p CHF2 、CN或鹵素；且p為0、1或2。Embodiment 2B The compound of Formula 1 , wherein R 1 b is H, CH 3 , CF 3 , OCF 3 , OCHF 2 , S(O) p CF 3 , S(O) p CHF 2 , CN or halogen; and p is 0, 1 or 2.

實施例2C式1 之化合物，其中R1 b 為CH3 、CF3 、OCF3 、OCHF2 、S(O)p CF3 、S(O)p CHF2 、CN或鹵素。Embodiment 2C A compound of formula 1 wherein R 1 b is CH 3 , CF 3 , OCF 3 , OCHF 2 , S(O) p CF 3 , S(O) p CHF 2 , CN or halogen.

實施例2D式1 之化合物，其中R1 b 為H、CH3 、CF3 、CN、F、Cl、Br或I。Embodiment 2D A compound of Formula 1 wherein R 1 b is H, CH 3 , CF 3 , CN, F, Cl, Br or I.

實施例2E式1 之化合物，其中R1 b 為CH3 、CF3 、CN、F、Cl、Br或I。Embodiment 2E A compound of Formula 1 wherein R 1 b is CH 3 , CF 3 , CN, F, Cl, Br or I.

實施例2F式1 之化合物，其中R1 b 為CN、F、Cl、Br或I。Embodiment 2F A compound of formula 1 wherein R 1 b is CN, F, Cl, Br or I.

實施例2G式1 之化合物，其中R1 b 為Cl、Br或CN。Embodiment 2G A compound of formula 1 wherein R 1 b is Cl, Br or CN.

實施例2H式1 之化合物，其中R1 b 為Cl或Br。Embodiment 2H A compound of formula 1 wherein R 1 b is Cl or Br.

實施例2I式1 之化合物，其中R1 b 為CN。Embodiment 2 is a compound of Formula 1 , wherein R 1 b is CN.

實施例2J式1 之化合物，其中R1 b 不為H。Embodiment 2J The compound of Formula 1 , wherein R 1 b is not H.

實施例2K式1 之化合物，其中R1 b 不為CN。Embodiment 2K A compound of formula 1 wherein R 1 b is not CN.

實施例3A式1 之化合物，其中R2 為H、C1 －C4 烷基、C2 －C4 烯基、C2 －C4 炔基、C3 －C6 環烷基、C2 －C6 烷基羰基或C2 －C6 烷氧基羰基。Embodiment 3A Compound of Formula 1 , wherein R 2 is H, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 2 - C 6 alkylcarbonyl or C 2 -C 6 alkoxycarbonyl.

實施例3B式1 之化合物，其中R2 為H。Embodiment 3B Compound of Formula 1 wherein R 2 is H.

實施例4A式1 之化合物，其中R3 為H、C1 －C4 烷基、C2 －C4 烯基、C2 －C4 炔基、C3 －C6 環烷基、C2 －C6 烷基羰基或C2 －C6 烷氧基羰基。Embodiment 4A A compound of Formula 1 wherein R 3 is H, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 2 - C 6 alkylcarbonyl or C 2 -C 6 alkoxycarbonyl.

實施例4B式1 之化合物，其中R3 為H。Embodiment 4B A compound of formula 1 wherein R 3 is H.

實施例5A式1 之化合物，其中R4 為視情況經1至6個選自CH3 及鹵素之取代基取代之C4 －C1 1 烷基環烷基。Embodiment 5A A compound of Formula 1 wherein R 4 is C 4 -C 1 1 alkylcycloalkyl optionally substituted with 1 to 6 substituents selected from CH 3 and halogen.

實施例5B式1 之化合物，其中R4 為視情況經1至6個選自CH3 及鹵素之取代基取代之1－甲基環烷基。Embodiment 5B A compound of formula 1 wherein R 4 is 1-methylcycloalkyl optionally substituted with from 1 to 6 substituents selected from CH 3 and halo.

實施例5C式1 之化合物，其中R4 為視情況經1至4個選自CH3 及鹵素之取代基取代之1－甲基環丙基。Embodiment 5C A compound of formula 1 wherein R 4 is 1-methylcyclopropyl optionally substituted with from 1 to 4 substituents selected from CH 3 and halo.

實施例5D式1 之化合物，其中R4 為視情況經1至4個選自CH3 及鹵素之取代基取代之1－甲基環丁基。Examples of compounds of formula 5D embodiment 1, wherein R 4 is optionally substituted with 1 to 4 heteroatoms selected from CH 3 and a halogen substituent of the substituted 1-methyl-cyclobutyl group.

實施例5E式1 之化合物，其中R4 為視情況經1至6個選自CH3 及鹵素之取代基取代之(C1 －C8 烷基)(C3 －C4 環烷基)。Embodiment 5E A compound of formula 1 wherein R 4 is (C 1 -C 8 alkyl) (C 3 -C 4 cycloalkyl) optionally substituted with from 1 to 6 substituents selected from CH 3 and halo.

實施例5F式1 之化合物，其中R4 為 視情況經1至6個選自CH3 及鹵素之取代基取代之(C2 －C8 烯基)(C3 －C4 環烷基)。Embodiment 5F A compound of formula 1 wherein R 4 is (C 2 -C 8 alkenyl) (C 3 -C 4 cycloalkyl) optionally substituted with from 1 to 6 substituents selected from CH 3 and halo.

實施例5G式1 之化合物，其中R4 為視情況經1至6個選自CH3 及鹵素之取代基取代之(C2 －C8 炔基)(C3 －C4 環烷基)。Embodiment 5G The compound of Formula 1 , wherein R 4 is (C 2 -C 8 alkynyl) (C 3 -C 4 cycloalkyl) substituted with 1 to 6 substituents selected from CH 3 and halogen, as appropriate.

實施例5H式1 之化合物，其中R4 為視情況經1至6個選自CH3 及鹵素之取代基取代之(C1 －C8 烷基)(C3 －C4 環烯基)。Embodiment 5H A compound of formula 1 wherein R 4 is (C 1 -C 8 alkyl) (C 3 -C 4 cycloalkenyl) optionally substituted with from 1 to 6 substituents selected from CH 3 and halogen.

實施例6A式1 之化合物，其中R4 為 視情況經1至6個選自CH3 及鹵素之取代基取代之C4 －C1 2 環烷基烷基。Embodiment 6A Compound of Formula 1 wherein R 4 is C 4 -C 1 2 cycloalkylalkyl optionally substituted with 1 to 6 substituents selected from CH 3 and halogen.

實施例6B式1 之化合物，其中R4 為環丙基甲基或環丁基甲基；各視情況經1至6個選自CH3 及鹵素之取代基取代。Embodiment 6B A compound of formula 1 wherein R 4 is cyclopropylmethyl or cyclobutylmethyl; each of which is optionally substituted with from 1 to 6 substituents selected from CH 3 and halogen.

實施例6C式1 之化合物，其中R4 為視情況經1至6個選自CH3 及鹵素之取代基取代之(C3 －C4 環烷基)(C1 －C8 烷基)。Embodiment 6C A compound of formula 1 wherein R 4 is (C 3 -C 4 cycloalkyl)(C 1 -C 8 alkyl) optionally substituted with from 1 to 6 substituents selected from CH 3 and halo.

實施例6D式1 之化合物，其中R4 為視情況經1至6個選自CH3 及鹵素之取代基取代之(C3 －C4 環烷基)(C2 －C8 烯基)。Embodiment 6D A compound of formula 1 wherein R 4 is (C 3 -C 4 cycloalkyl) (C 2 -C 8 alkenyl) optionally substituted with from 1 to 6 substituents selected from CH 3 and halo.

實施例6E式1 之化合物，其中R4 為視情況經1至6個選自CH3 及鹵素之取代基取代之(C3 －C4 環烷基)(C2 －C8 炔基)。Embodiment 6E A compound of formula 1 wherein R 4 is (C 3 -C 4 cycloalkyl) (C 2 -C 8 alkynyl) optionally substituted with from 1 to 6 substituents selected from CH 3 and halo.

實施例6F式1 之化合物，其中R4 為視情況經1至6個選自CH3 及鹵素之取代基取代之(C3 －C4 環烯基)(C1 －C8 烷基)。Embodiment 6F A compound of formula 1 wherein R 4 is (C 3 -C 4 cycloalkenyl) (C 1 -C 8 alkyl) optionally substituted with 1 to 6 substituents selected from CH 3 and halogen.

實施例6G式1 之化合物，其中R4 不為視情況經取代的C4 －C6 環烷基烷基。Embodiment 6G A compound of Formula 1 wherein R 4 is not optionally substituted C 4 -C 6 cycloalkylalkyl.

實施例6H式1 之化合物，其中R4 不為視情況經取代的(C3 －C4 環烷基)(C1 －C6 烷基)。Embodiment 6H A compound of formula 1 wherein R 4 is not optionally substituted (C 3 -C 4 cycloalkyl) (C 1 -C 6 alkyl).

實施例6I式1 之化合物，其中R4 不為環丙基甲基。Examples of the compound of Formula 6I embodiment 1, wherein R 4 is not cyclopropylmethyl.

實施例6J式1 之化合物，其中R4 不為1－環丙基乙基。Embodiment 6J A compound of formula 1 wherein R 4 is not 1-cyclopropylethyl.

實施例6K式1 之化合物，其中R4 不為(2－甲基環丙基)甲基。Embodiment 6K A compound of formula 1 wherein R 4 is not (2-methylcyclopropyl)methyl.

實施例6L式1 之化合物，其中R4 不為(2,2－二氯－1－甲基環丙基)甲基。Examples of compounds of formula 6L embodiment 1, wherein R 4 is not (2,2-dichloro-1-methylcyclopropyl) methyl.

實施例6M式1 之化合物，其中R4 不為(1－甲基環丙基)甲基。Embodiment 6M A compound of Formula 1 wherein R 4 is not (1-methylcyclopropyl)methyl.

實施例6N式1 之化合物，其中R4 不為1－環丁基乙基。Embodiment 6 N The compound of Formula 1 , wherein R 4 is not 1-cyclobutylethyl.

實施例7A式1 之化合物，其中R4 為1－甲基環丙基、環丙基甲基或1－環丙基乙基，各視情況在環丙基上經1至2個鹵素取代。Embodiment 7A A compound of formula 1 wherein R 4 is 1-methylcyclopropyl, cyclopropylmethyl or 1-cyclopropylethyl, each optionally substituted with 1 to 2 halogens on the cyclopropyl group.

實施例7B式1 之化合物，其中R4 為1－甲基環丙基、環丙基甲基或1－環丙基乙基。Embodiment 7B A compound of formula 1 wherein R 4 is 1-methylcyclopropyl, cyclopropylmethyl or 1-cyclopropylethyl.

實施例7C式1 之化合物，其中R4 為1－甲基環丙基、環丙基甲基或1－環丙基乙基，各在環丙基上經兩個鹵素取代。Embodiment 7C A compound of formula 1 wherein R 4 is 1-methylcyclopropyl, cyclopropylmethyl or 1-cyclopropylethyl, each substituted on the cyclopropyl by two halogens.

實施例7D式1 之化合物，其中R4 為1－甲基環丙基，其視情況在環丙基上經1至2個鹵素取代。Example 7D of the compound of Formula embodiment 1, wherein R 4 is 1-methyl-cyclopropyl, which are optionally substituted with 1 to 2 halogen substituents on the cyclopropyl.

實施例7E式1 之化合物，其中R4 為1－甲基環丙基。Embodiment 7E A compound of Formula 1 wherein R 4 is 1-methylcyclopropyl.

實施例7F式1 之化合物，其中R4 為環丙基甲基或1－環丙基乙基，各視情況在環丙基上經1至2個鹵素取代。Embodiment 7F A compound of formula 1 wherein R 4 is cyclopropylmethyl or 1-cyclopropylethyl, each optionally substituted with 1 to 2 halogens on the cyclopropyl group.

實施例7G式1 之化合物，其中R4 為環丙基甲基或1－環丙基乙基。Embodiment 7G A compound of formula 1 wherein R 4 is cyclopropylmethyl or 1-cyclopropylethyl.

實施例7H式1 之化合物，其中R4 為環丙基甲基，其視情況在環丙基上經1至2個鹵素取代。Embodiment 7H A compound of formula 1 wherein R 4 is cyclopropylmethyl, optionally substituted with 1 to 2 halogens on the cyclopropyl group.

實施例7I式1 之化合物，其中R4 為環丙基甲基。Embodiment 7 Formula 1 Formula 1 wherein R 4 is cyclopropylmethyl.

實施例7J式1 之化合物，其中R4 為1－環丙基乙基，其視情況在環丙基上經1至2個鹵素取代。Embodiment 7J A compound of formula 1 wherein R 4 is 1-cyclopropylethyl optionally substituted with 1 to 2 halogens on the cyclopropyl group.

實施例7K式1 之化合物，其中R4 為1－環丙基乙基。Embodiment 7K A compound of formula 1 wherein R 4 is 1-cyclopropylethyl.

實施例7L式1 之化合物，其中R4 不為1－甲基環丙基。Examples of the compound of Formula 7L embodiment 1, wherein R 4 is not a 1-methylcyclopropyl.

實施例7M式1 之化合物，其中R4 不為視情況經取代之1－甲基環丙基。Embodiment 7M A compound of Formula 1 wherein R 4 is not optionally substituted 1-methylcyclopropyl.

實施例7N式1 之化合物，其中R4 不為視情況經取代之C4 －C1 2 烷基環烷基。Embodiment 7 N A compound of formula 1 wherein R 4 is not optionally substituted C 4 -C 1 2 alkylcycloalkyl.

實施例7O式1 之化合物，其中R4 不為視情況經取代之C5 －C1 2 烯基環烷基。Embodiment 7O A compound of Formula 1 wherein R 4 is not optionally substituted C 5 -C 1 2 alkenylcycloalkyl.

實施例7P式1 之化合物，其中R4 不為視情況經取代之C5 －C1 2 炔基環烷基。Embodiment 7P A compound of formula 1 wherein R 4 is not optionally substituted C 5 -C 1 2 alkynylcycloalkyl.

實施例7Q式1 之化合物，其中R4 不為視情況經取代之C4 －C1 2 環烷基烷基。Embodiment 7Q A compound of Formula 1 wherein R 4 is not optionally substituted C 4 -C 1 2 cycloalkylalkyl.

實施例7R式1 之化合物，其中R4 不為視情況經取代之C5 －C1 2 環烷基烯基。Embodiment 7R A compound of formula 1 wherein R 4 is not optionally substituted C 5 -C 1 2 cycloalkylalkenyl.

實施例7S式1 之化合物，其中R4 不為視情況經取代之C5 －C1 2 環烷基炔基。Embodiment 7S A compound of Formula 1 , wherein R 4 is not optionally substituted C 5 -C 1 2 cycloalkylalkynyl.

實施例7T式1 之化合物，其中R4 不為視情況經取代之C4 －C1 2 環烯基烷基。Embodiment 7T A compound of formula 1 wherein R 4 is not optionally substituted C 4 -C 1 2 cycloalkenylalkyl.

實施例7U式1 之化合物，其中R4 不為視情況經取代之C4 －C1 2 烷基環烯基。Examples of the compound of Formula 7U embodiment 1, wherein R 4 is not optionally substituted the C 4 -C 1 2 alkyl cycloalkenyl.

實施例7V式1 之化合物，其中R4 不為1－甲基環丙基，且R1 b 不為H。Examples of the compound of Formula 1 7V embodiment, wherein R 4 is not a 1-methylcyclopropyl, and R 1 b is not H.

實施例8A式1 之化合物，其中R4 為C3 －C5 環氧乙烷基烷基、C4 －C6 環氧丙烷基烷基或3－環氧丙烷基，各視情況經1至2個獨立選自CH3 、CF3 、鹵素、CN及C(O)OCH3 之取代基取代。Embodiment 8A A compound of Formula 1 wherein R 4 is C 3 -C 5 oxiranylalkyl, C 4 -C 6 epoxypropanealkyl or 3-epoxypropenyl, each optionally 1 through Two substituents independently selected from the group consisting of CH 3 , CF 3 , halogen, CN, and C(O)OCH 3 are substituted.

實施例8B式1 之化合物，其中R4 為環氧乙烷基甲基、2－環氧丙烷基甲基、3－環氧丙烷基甲基或3－環氧丙烷基，各視情況經1至2個CH3 取代。Embodiment 8B A compound of formula 1 wherein R 4 is oxiranylmethyl, 2-epoxypropanylmethyl, 3-epoxypropanylmethyl or 3-epoxypropane, each optionally Up to 2 CH 3 substitutions.

實施例8C式1 之化合物，其中R4 為環氧乙烷基甲基。Embodiment 8C A compound of formula 1 wherein R 4 is oxiranylmethyl.

實施例8D式1 之化合物，其中R4 為2－環氧丙烷基甲基。Embodiment 8D A compound of formula 1 wherein R 4 is 2-epoxypropanylmethyl.

實施例8E式1 之化合物，其中R4 為3－環氧丙烷基甲基。Embodiment 8E A compound of Formula 1 wherein R 4 is 3-epoxypropanylmethyl.

實施例8F式1 之化合物，其中R4 為3－環氧丙烷基。Embodiment 8F A compound of formula 1 wherein R 4 is 3-epoxypropane.

實施例8G式1 之化合物，其中R4 不為視情況經取代之環氧乙烷基甲基。Embodiment 8G A compound of formula 1 wherein R 4 is not an optionally substituted oxiranylmethyl group.

實施例8H式1 之化合物，其中R4 不為視情況經取代之2－環氧丙烷基甲基。Embodiment 8H A compound of formula 1 wherein R 4 is not optionally substituted 2-epoxypropanylmethyl.

實施例8I式1 之化合物，其中R4 不為視情況經取代之3－環氧丙烷基甲基。Embodiment 8 Formula I Formula 1 wherein R 4 is not optionally substituted 3-epoxypropanylmethyl.

實施例8J式1 之化合物，其中R4 不為視情況經取代之C3 －C5 環氧乙烷基烷基、C3 －C5 硫雜環丙烷基烷基、C4 －C6 環氧丙烷基烷基、C4 －C6 硫雜環丁烷基烷基、3－環氧丙烷基或3－硫雜環丁烷基。Embodiment 8J The compound of Formula 1 , wherein R 4 is not optionally substituted C 3 -C 5 oxiranylalkyl, C 3 -C 5 thiacyclopropylalkyl, C 4 -C 6 ring Oxypropanylalkyl, C 4 -C 6 thietanealkyl, 3-epoxypropane or 3-thietyl.

實施例8K式1 之化合物，其中R4 不為視情況經取代之C3 －C5 吖丙啶基烷基、C4 －C6 吖丁啶基烷基或3－吖丁啶基。Embodiment 8K A compound of formula 1 wherein R 4 is not optionally substituted C 3 -C 5 aziridinylalkyl, C 4 -C 6 azetidinylalkyl or 3-azetidinyl.

實施例9A式1 之化合物，其中R4 為吖丙啶基甲基、2－吖丁啶基甲基、3－吖丁啶基甲基或3－吖丁啶基，各具有R1 0 連接至氮原子，且視情況在碳原子上經1至2個獨立選自CH3 、CF3 、鹵素、CN及C(O)OCH3 之取代基取代。Embodiment 9A Compound of Formula 1 , wherein R 4 is aziridinylmethyl, 2-azetidinylmethyl, 3-azetidinylmethyl or 3-azetidinyl, each having R 1 0 attached to a nitrogen atom, and The case is substituted on the carbon atom with 1 to 2 substituents independently selected from CH 3 , CF 3 , halogen, CN and C(O)OCH 3 .

實施例9B式1 之化合物，其中R4 為吖丙啶基甲基、2－吖丁啶基甲基、3－吖丁啶基甲基或3－吖丁啶基，各具有R1 0 連接至氮原子，且視情況在碳原子上經1至2個CH3 取代。Embodiment 9B A compound of formula 1 wherein R 4 is aziridinylmethyl, 2-azetidinylmethyl, 3-azetidinylmethyl or 3-azetidinyl, each having R 1 0 attached to a nitrogen atom, and The situation is substituted with 1 to 2 CH 3 on the carbon atom.

實施例9C式1 之化合物，其中R1 0 為H或C1 －C3 烷基。Embodiment 9C A compound of formula 1 wherein R 1 0 is H or C 1 -C 3 alkyl.

實施例10A式1 之化合物，其中各R6 係獨立選自由H、CH3 、CF3 、CH2 CF3 、CHF2 、OCH2 CF3 、OCHF2 及鹵素組成之群。Example 10A Compound of Formula embodiment 1, wherein each R 6 is independently selected from the group consisting of line H, CH 3, CF 3, CH 2 CF 3, CHF 2, OCH 2 CF 3, OCHF 2 and the group consisting of halo.

實施例10B式1 之化合物，其中各R6 獨立為鹵素、OCH2 CF3 、OCHF2 或CF3 。Embodiment 10B A compound of formula 1 wherein each R 6 is independently halogen, OCH 2 CF 3 , OCHF 2 or CF 3 .

實施例10C式1 之化合物，其中各R6 獨立為Cl、Br、OCH2 CF3 或CF3 。Embodiment 10C A compound of formula 1 wherein each R 6 is independently Cl, Br, OCH 2 CF 3 or CF 3 .

實施例10D式1 之化合物，其中各R6 為Cl、Br、CF3 或C1 －C2 氟烷氧基。Embodiment 10D A compound of Formula 1 wherein each R 6 is Cl, Br, CF 3 or C 1 -C 2 fluoroalkoxy.

實施例11A式1 之化合物，其中R7 為視情況經1至3個選自R9 之取代基取代之苯環。Example 11A Compound of Formula 1 embodiment, wherein R 7 is optionally substituted with 1-3 substituents selected from the substituent R 9 group of the phenyl ring.

實施例11B式1 之化合物，其中各R9 獨立為H、C1 －C4 烷基、C1 －C4 鹵烷基、鹵素或CN。Embodiment 11B A compound of formula 1 wherein each R 9 is independently H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halo or CN.

實施例11C式1 之化合物，其中R7 為 Embodiment 11C Compound of Formula 1 , wherein R 7 is

實施例11D式1 之化合物，其中各R9 獨立為H、CH3 、CF3 、CN或鹵素。Embodiment 11D A compound of Formula 1 wherein each R 9 is independently H, CH 3 , CF 3 , CN or halogen.

實施例12A式1 之化合物，其中R7 為 Embodiment 12A Compound of formula 1 wherein R 7 is

實施例12B式1 之化合物，其中各R9 獨立為C1 －C4 烷基、C1 －C4 鹵烷基、鹵素或CN；且s為0、1或2。Embodiment 12B Compound of Formula 1 wherein each R 9 is independently C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halo or CN; and s is 0, 1 or 2.

實施例12C式1 之化合物，其中R7 為 Embodiment 12C Compound of formula 1 wherein R 7 is

實施例12D式1 之化合物，其中各R9 獨立為H、CH3 、CF3 、CN或鹵素。Embodiment 12D A compound of Formula 1 wherein each R 9 is independently H, CH 3 , CF 3 , CN or halogen.

實施例13A式1 之化合物，其中R8 為C1 －C4 烷基或C1 －C4 鹵烷基。Embodiment 13A A compound of Formula 1 wherein R 8 is C 1 -C 4 alkyl or C 1 -C 4 haloalkyl.

實施例13B式1 之化合物，其中R8 為CH2 CF3 或CHF2 。Embodiment 13B Compound of Formula 1 wherein R 8 is CH 2 CF 3 or CHF 2 .

實施例14A式1 之化合物，其中J為視情況經1至4個R5 取代之苯基。Embodiment 14A Compound of Formula 1 wherein J is phenyl substituted with from 1 to 4 R 5 as appropriate.

實施例14B式1 之化合物，其中各R5 獨立為C1 －C4 烷基、C1 －C4 鹵烷基、C1 －C2 鹵烷氧基、鹵素或CN。Embodiment 14B A compound of formula 1 wherein each R 5 is independently C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 2 haloalkoxy, halo or CN.

實施例15A式1 之化合物，其中J為選自由J－1、J－2、J－3、J－4、J－5、J－6、J－7及J－8組成之群之雜環。The compound of the formula 1 wherein R is a heterocyclic ring selected from the group consisting of J-1, J-2, J-3, J-4, J-5, J-6, J-7 and J-8. .

實施例15B式1 之化合物，其中J為J－1、J－2、J－4、J－7或J－8。Embodiment 15B A compound of formula 1 wherein J is J-1, J-2, J-4, J-7 or J-8.

實施例15C式1 之化合物，其中J為J－1、J－2或J－4。Embodiment 15C A compound of formula 1 wherein J is J-1, J-2 or J-4.

實施例15D式1 之化合物，其中J為J－7或J－8。Embodiment 15D A compound of Formula 1 wherein J is J-7 or J-8.

實施例15E式1 之化合物，其中J為J－1。Embodiment 15E A compound of formula 1 wherein J is J-1.

實施例15F式1 之化合物，其中J為J－2。Embodiment 15F A compound of formula 1 wherein J is J-2.

實施例15G式1 之化合物，其中J為J－3。Embodiment 15G A compound of formula 1 wherein J is J-3.

實施例15H式1 之化合物，其中J為J－4。Embodiment 15H A compound of formula 1 wherein J is J-4.

實施例15I式1 之化合物，其中J為J－5。Embodiment 15I Compound of formula 1 wherein J is J-5.

實施例15J式1 之化合物，其中J為J－6。Embodiment 15J Compound of formula 1 wherein J is J-6.

實施例15K式1 之化合物，其中J為J－7。Embodiment 15K Compound of Formula 1 , wherein J is J-7.

實施例15L式1 之化合物，其中J為J－8。Embodiment 15 L Compound of Formula 1 , wherein J is J-8.

本發明之實施例，包括以上實施例1A－15L以及本文所描述之任何其他實施例，可以任何方式組合，且該等實施例中變數的說明不僅適合式1 之化合物而且適合可用於製備式1 化合物之起始化合物及中間化合物，包括式10 化合物。另外，本發明之實施例，包括以上實施例1A－15L以及本文所描述之任何其他實施例及其任何組合適合於本發明之組合物、混合物及方法，其可包含該實施例及其任何組合中所描述的化合物。Embodiments of the present invention, including the above Examples 1A-15L and any other embodiments described herein, may be combined in any manner, and the description of the variables in the Examples is not only suitable for the compound of Formula 1 but also suitable for the preparation of Formula 1 Starting compounds and intermediate compounds of the compounds, including compounds of formula 10 . Additionally, embodiments of the invention, including the above Examples 1A-15L, and any other embodiments described herein, and any combination thereof, are suitable for the compositions, mixtures and methods of the invention, which may comprise the embodiment and any combination thereof The compounds described in the above.

實施例1A－15L之組合之實例包括：實施例A式1 之化合物，其中：R1 a 為C1 －C4 烷基、C1 －C4 鹵烷基、鹵素、CN、NO2 、C1 －C4 烷氧基、C1 －C4 鹵烷氧基、C1 －C4 烷基硫基、C1 －C4 烷基亞磺醯基、C1 －C4 烷基磺醯基、C1 －C4 鹵烷基硫基、C1 －C4 鹵烷基亞磺醯基或C1 －C4 鹵烷基磺醯基；R1 b 為H、C1 －C4 烷基、C1 －C4 鹵烷基、鹵素、CN、NO2 、C1 －C4 烷氧基、C1 －C4 鹵烷氧基、C1 －C4 烷基硫基、C1 －C4 烷基亞磺醯基、C1 －C4 烷基磺醯基、C1 －C4 鹵烷基硫基、C1 －C4 鹵烷基亞磺醯基或C1 －C4 鹵烷基磺醯基；R2 及R3 各自獨立為H、C1 －C4 烷基、C2 －C4 烯基、C2 －C4 炔基、C3 －C6 環烷基、C2 －C6 烷基羰基或C2 －C6 烷氧基羰基；且R4 為C4 －C1 2 烷基環烷基或C4 －C1 2 環烷基烷基，各視情況經1至6個選自CH3 及鹵素之取代基取代；或R4 為C3 －C5 環氧乙烷基烷基、C4 －C6 環氧丙烷基烷基或3－環氧丙烷基，各視情況經1至2個獨立選自CH3 、CF3 、鹵素、CN及C(O)OCH3 之取代基取代。Examples 1A-15L compositions of the embodiments include: A compound of Formula 1 of Example Embodiment, wherein: R 1 a is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halo, CN, NO 2, C 1- C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl , C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl or C 1 -C 4 haloalkylsulfonyl; R 1 b is H, C 1 -C 4 alkyl , C 1 -C 4 haloalkyl, halogen, CN, NO 2 , C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl or C 1 -C 4 halo Alkylsulfonyl; R 2 and R 3 are each independently H, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkylcarbonyl or C 2 -C 6 alkoxycarbonyl; and R 4 is C 4 -C 1 2 alkylcycloalkyl or C 4 -C 1 2 cycloalkylalkyl, each optionally to 6 selected from CH 3 and the halo substituents; or R 4 is C 3 -C 5 ethylene oxide Alkyl, C 4 -C 6 alkyl group, or 3-propylene oxide propylene oxide group, each optionally substituted with 1 to 2 substituents independently selected from CH 3, CF 3, halo, CN and C (O) OCH 3 of Substituent substitution.

實施例A1式1 之化合物，其中：R1 a 為C1 －C4 烷基、C1 －C4 鹵烷基、鹵素、CN、NO2 、C1 －C4 烷氧基、C1 －C4 鹵烷氧基、C1 －C4 烷基硫基、C1 －C4 烷基亞磺醯基、C1 －C4 烷基磺醯基、C1 －C4 鹵烷基硫基、C1 －C4 鹵烷基亞磺醯基或C1 －C4 鹵烷基磺醯基；R1 b 為H、C1 －C4 烷基、C1 －C4 鹵烷基、鹵素、CN、NO2 、C1 －C4 烷氧基、C1 －C4 鹵烷氧基、C1 －C4 烷基硫基、C1 －C4 烷基亞磺醯基、C1 －C4 烷基磺醯基、C1 －C4 鹵烷基硫基、C1 －C4 鹵烷基亞磺醯基或C1 －C4 鹵烷基磺醯基；R2 及R3 各自獨立為H、C1 －C4 烷基、C2 －C4 烯基、C2 －C4 炔基、C3 －C6 環烷基、C2 －C6 烷基羰基或C2 －C6 烷氧基羰基；且R4 為(C1 －C8 )烷基(C3 －C4 )環烷基或(C3 －C4 )環烷基(C1 －C8 )烷基，各視情況經1至6個選自CH3 及鹵素之取代基取代；或R4 為C3 －C5 環氧乙烷基烷基、C4 －C6 環氧丙烷基烷基或3－環氧丙烷基，各視情況經1至2個獨立選自CH3 、CF3 、鹵素、CN及C(O)OCH3 之取代基取代。The compound of formula 1 of embodiment example A1, wherein: R 1 a is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halo, CN, NO 2, C 1 -C 4 alkoxy, C 1 - C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio , C 1 -C 4 haloalkylsulfinyl or C 1 -C 4 haloalkylsulfonyl; R 1 b is H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halogen , CN, NO 2 , C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 - C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl or C 1 -C 4 haloalkylsulfonyl; each of R 2 and R 3 Independently H, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkylcarbonyl or C 2 -C 6 alkoxycarbonyl; and R 4 is (C 1 -C 8 )alkyl(C 3 -C 4 )cycloalkyl or (C 3 -C 4 )cycloalkyl(C 1 -C 8 )alkyl, Each optionally substituted with 1 to 6 substituents selected from CH 3 and halogen; or R 4 is C 3 -C 5 oxiranylalkyl, C 4 -C 6 propylene oxide alkyl or 3-epoxypropane group, each optionally substituted with 1 to 2 substituents independently selected from CH 3 , CF 3 , halogen, CN and C(O)OCH 3 .

實施例B實施例A或A1之化合物，其中：R1 a 為CH3 、CF3 、OCF3 、OCHF2 、S(O)n CF3 、S(O)n CHF2 、CN或鹵素；R1 b 為H、CH3 、CF3 、OCF3 、OCHF2 、S(O)p CF3 、S(O)p CHF2 、CN或鹵素；R2 及R3 為H；n為0、1或2；且p為0、1或2。Embodiment B The compound of Embodiment A or A1, wherein: R 1 a is CH 3 , CF 3 , OCF 3 , OCHF 2 , S(O) n CF 3 , S(O) n CHF 2 , CN or halogen; 1 b is H, CH 3 , CF 3 , OCF 3 , OCHF 2 , S(O) p CF 3 , S(O) p CHF 2 , CN or halogen; R 2 and R 3 are H; n is 0, 1 Or 2; and p is 0, 1, or 2.

實施例C實施例B之化合物，其中：各R5 獨立為C1 －C4 烷基、C1 －C4 鹵烷基、C1 －C2 鹵烷氧基、鹵素或CN；各R6 獨立為H、CH3 、CF3 、CH2 CF3 、CHF2 、OCH2 CF3 、OCHF2 或鹵素；R7 為視情況經1至3個選自R9 之取代基取代之苯基；或R7 為 各R9 獨立為C1 －C4 烷基、C1 －C4 鹵烷基、鹵素或CN；R8 為CH2 CF3 或CHF2 ；且s為0、1或2。Embodiment C The compound of Embodiment B wherein: each R 5 is independently C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 2 haloalkoxy, halogen or CN; each R 6 Independently H, CH 3 , CF 3 , CH 2 CF 3 , CHF 2 , OCH 2 CF 3 , OCHF 2 or halogen; R 7 is a phenyl group optionally substituted with 1 to 3 substituents selected from R 9 ; Or R 7 is Each R 9 is independently C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halogen or CN; R 8 is CH 2 CF 3 or CHF 2 ; and s is 0, 1 or 2.

實施例D實施例C之化合物，其中：各R6 獨立為鹵素、OCH2 CF3 、OCHF2 或CF3 ；R7 為或；且各R9 獨立為H、CH3 、CF3 、CN或鹵素。Embodiment D The compound of Embodiment C wherein: each R 6 is independently halogen, OCH 2 CF 3 , OCHF 2 or CF 3 ; R 7 is or And each R 9 is independently H, CH 3 , CF 3 , CN or halogen.

實施例E式D之化合物，其中J為J－1、J－2、J－4、J－7或J－8。Embodiment E Compound of Formula D wherein J is J-1, J-2, J-4, J-7 or J-8.

實施例F實施例E之化合物，其中：R1 a 為CH3 、F、Cl、Br或I；R1 b 為H、CH3 、CF3 、CN、F、Cl、Br或I；且各R6 獨立為Cl、Br、OCH2 CF3 或CF3 。Embodiment F The compound of Embodiment E wherein: R 1 a is CH 3 , F, Cl, Br or I; R 1 b is H, CH 3 , CF 3 , CN, F, Cl, Br or I; R 6 is independently Cl, Br, OCH 2 CF 3 or CF 3 .

實施例G實施例F之化合物，其中：J為J－2、J－4、J－7或J－8；且R4 為1－甲基環丙基、1－甲基環丁基、環丙基甲基或環丁基甲基；各視情況經1至4個CH3 或鹵素取代；或R4 為環氧乙烷基甲基、2－環氧丙烷基甲基、3－環氧丙烷基甲基或3－環氧丙烷基，各視情況經1至2個CH3 取代。Embodiment G The compound of Embodiment F, wherein: J is J-2, J-4, J-7 or J-8; and R 4 is 1-methylcyclopropyl, 1-methylcyclobutyl, ring Propylmethyl or cyclobutylmethyl; each optionally substituted with 1 to 4 CH 3 or halogen; or R 4 is oxiranylmethyl, 2-epoxypropanemethyl, 3-epoxypropanyl Methyl or 3-epoxypropane groups, each optionally substituted with 1 to 2 CH 3 .

實施例H實施例F之化合物，其中：J為J－1；且R4 為1－甲基環丙基、1－甲基環丁基、環丙基甲基或環丁基甲基；各視情況經1至4個CH3 或鹵素取代；或R4 為環氧乙烷基甲基、2－環氧丙烷基甲基、3－環氧丙烷基甲基或3－環氧丙烷基，各視情況經1至2個CH3 取代；其限制條件為當R4 為1－甲基環丙基時，則R1 b 不為H。Embodiment H The compound of Embodiment F wherein: J is J-1; and R 4 is 1-methylcyclopropyl, 1-methylcyclobutyl, cyclopropylmethyl or cyclobutylmethyl; Substituted with 1 to 4 CH 3 or halogen; or R 4 is oxiranylmethyl, 2-epoxypropanemethyl, 3-epoxypropanemethyl or 3-epoxypropenyl, each The case is substituted with 1 to 2 CH 3 ; the restriction is that when R 4 is 1-methylcyclopropyl, then R 1 b is not H.

特定實施例包括選自以下物質組成之群之式1 化合物：1－(3－氯－2－吡啶基)－N －[4－氰基－2－[[(環丙基甲基)胺基]羰基]－6－甲基苯基]－3－(三氟甲基)－1H －吡唑－5－甲醯胺；3－溴－N －[4－氯－2－[[(環丙基甲基)胺基]羰基]－6－甲基苯基]－1－(3－氯－2－吡啶基)－1H －吡唑－5－甲醯胺；3－溴－1－(3－氯－2－吡啶基)－N －[2,4－二氯－6－[[(2－環氧丙烷基甲基)胺基]羰基]苯基]－1H －吡唑－5－甲醯胺；3－溴－N －[4－氯－2－甲基－6－[[(2－環氧丙烷基甲基)胺基]羰基]苯基]－1－(3－氯－2－吡啶基)－1H －吡唑－5－甲醯胺；3－氯－1－(3－氯－2－吡啶基)－N －[2,4－二氯－6－[[(2－環氧丙烷基甲基)胺基]羰基]苯基]－1H －吡唑－5－甲醯胺；1－(2－氯苯基)－N －[4－氰基－2－甲基－6－[[(2－環氧丙烷基甲基)胺基]羰基]苯基]－3－(三氟甲基)－1H －吡唑－5－甲醯胺；3－溴－1－(3－氯－2－吡啶基)－N －[4－氰基－2－甲基－6－[[(2－環氧丙烷基甲基)胺基]羰基]苯基]－1H －吡唑－5－甲醯胺；3－溴－N －[4－氯－2－甲基－6－[[(1－甲基環丙基)胺基]羰基]苯基]－1－(3－氯－2－吡啶基)－1H －吡唑－5－甲醯胺；3－溴－1－(3－氯－2－吡啶基)－N －[2,4－二氯－6－[[(1－甲基環丙基)胺基]羰基]苯基]－1H －吡唑－5－甲醯胺；3－溴－1－(3－氯－2－吡啶基)－N －[4－氰基－2－甲基－6－[[(1－甲基環丙基)胺基]羰基]苯基]－1H －吡唑－5－甲醯胺；3－溴－1－(2－氯苯基)－N －[4－氰基－2－[[(環丙基甲基)胺基]羰基]－6－甲基苯基]－1H －吡唑－5－甲醯胺；3－溴－N －[4－氯－2－[[(環丙基甲基)胺基]羰基]－6－甲基苯基]－1－(2－氯苯基)－1H －吡唑－5－甲醯胺；3－溴－N －[4－氯－2－[[(1－環丙基乙基)胺基]羰基]－6－甲基苯基]－1－(3－氯－2－吡啶基)－1H －吡唑－5－甲醯胺；3－溴－N －[4－氯－2－[[(1－環丙基乙基)胺基]羰基]－6－甲基苯基]－1－(2－氯苯基)－1H －吡唑－5－甲醯胺；及3－溴－1－(3－氯－2－吡啶基)－N －[4－氰基－2－[[(1－環丙基乙基)胺基]羰基]－6－甲基苯基]－1H －吡唑－5－甲醯胺。Particular embodiments include the composition of the group of compounds of formula selected from the following 1: 1- (3-chloro-2-pyridinyl) - N - [4- cyano-2 - [[(cyclopropylmethyl) amino ]carbonyl]-6-methylphenyl]-3-(trifluoromethyl)-1 H -pyrazole-5-carboxamide; 3-bromo- N- [4-chloro-2-[[( Propylmethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridyl)-1 H -pyrazole-5-formamide; 3-bromo-1- (3-chloro-2-pyridinyl) - N - [2,4- dichloro-6 - [[(2-oxetanylmethyl) amino] carbonyl] phenyl] -1 H - pyrazol - 5-carbamide; 3-bromo- N- [4-chloro-2-methyl-6-[[(2-epoxypropenylmethyl)amino]carbonyl]phenyl]-1-(3- chloro-2-pyridinyl) -1 H - pyrazole-5-acyl-amine; 3-chloro-1- (3-chloro-2-pyridinyl) - N - [2,4- dichloro-6- [ [(2-oxetanylmethyl) amino] carbonyl] phenyl] -1 H - pyrazole-5-acyl-amine; 1- (2-chlorophenyl) - N - [4- cyano - 2- methyl-6 - [[(2-oxetanylmethyl) amino] carbonyl] phenyl] -3- (trifluoromethyl) -1 H - pyrazol 5-Amides; 3-bromo-1- (3-chloro-2-pyridinyl) - N - [4- cyano-2-methyl-6 - [[(2-oxetanylmethyl) Amino]carbonyl]phenyl]-1 H -pyrazole-5-formamide; 3-bromo- N- [4-chloro-2-methyl-6-[[(1-methylcyclopropyl)) Amino]carbonyl]phenyl]-1-(3-chloro-2-pyridyl)-1 H -pyrazole-5-formamide; 3-bromo-1-(3-chloro-2-pyridyl) - N -[2,4-Dichloro-6-[[(1-methylcyclopropyl)amino]carbonyl]phenyl]-1 H -pyrazole-5-carboxamide; 3-bromo-1 - (3-chloro-2-pyridinyl) - N - [4- cyano-2-methyl-6 - [[(1-methylcyclopropyl) amino] carbonyl] phenyl] -1 H - pyrazole-5-acyl-amine; 3-bromo-1- (2-chlorophenyl) - N - [4- cyano-2 - [[(cyclopropylmethyl) amino] carbonyl] -6- Methylphenyl]-1 H -pyrazole-5-formamide; 3-bromo- N- [4-chloro-2-[[(cyclopropylmethyl)amino]carbonyl]-6-methyl Phenyl]-1-(2-chlorophenyl)-1 H -pyrazole-5-carboxamide; 3-bromo- N- [4-chloro-2-[[(1-cyclopropylethyl)) Amino]carbonyl]-6 Methylphenyl] -1- (3-chloro-2-pyridinyl) -1 H - pyrazole-5-acyl-amine; 3-Bromo - N - [4- chloro-2 - [[(1- Propylethyl)amino]carbonyl]-6-methylphenyl]-1-(2-chlorophenyl)-1 H -pyrazole-5-carboxamide; and 3-bromo-1-(3) - chloro-2-pyridinyl) - N - [4- cyano-2 - [[(1-cyclopropylethyl) amino] carbonyl] -6-methylphenyl] -1 H - pyrazol - 5-carbamamine.

另外特定實施例包括選自緊接上文之群組之式1 化合物的任何組合。Further specific embodiments include any combination of compounds of formula 1 selected from the group immediately preceding.

作為本發明之實施例同樣值得關注的為包含任何前述實施例以及本文所述任何其他實施例之化合物及其任何組合以及至少一種選自由界面活性劑、固體稀釋劑及液體稀釋劑組成之群之額外組份的組合物，該組合物視情況另外包含至少一種額外的生物活性化合物或藥劑。Also of interest as an embodiment of the present invention are compounds comprising any of the foregoing examples, and any other embodiments described herein, and any combination thereof, and at least one selected from the group consisting of surfactants, solid diluents, and liquid diluents. An additional component of the composition, which optionally comprises at least one additional biologically active compound or agent.

作為本發明之實施例同樣值得關注的為用於控制無脊椎害蟲之組合物，其包含生物有效量的任何前述實施例以及本文所述任何其他實施例之化合物及其任何組合以及至少一種選自由界面活性劑、固體稀釋劑及液體稀釋劑組成之群之額外組份，該組合物視情況另外包含生物有效量的至少一種額外的生物活性化合物或藥劑。本發明之實施例另外包括用於控制無脊椎害蟲之方法，其包含使該無脊椎害蟲或其環境與生物有效量的任何前述實施例以及本文所述任何其他實施例之化合物及其任何組合(例如以本文所述組合物之形式)接觸。Also of interest as an embodiment of the present invention is a composition for controlling an invertebrate pest comprising a biologically effective amount of any of the foregoing embodiments, and any other embodiments of the compounds described herein, and any combination thereof, and at least one selected from the group consisting of An additional component of the group consisting of a surfactant, a solid diluent, and a liquid diluent, the composition optionally further comprising a biologically effective amount of at least one additional bioactive compound or agent. Embodiments of the invention additionally include methods for controlling an invertebrate pest comprising any of the foregoing embodiments of the invertebrate pest or an environmentally and biologically effective amount thereof, and any other embodiments of the compounds described herein, and any combination thereof ( Contact, for example, in the form of a composition described herein.

本發明之實施例亦包括土壤浸潤液體調配物形式之組合物，其包含任何前述實施例以及本文所述任何其他實施例之化合物及其任何組合。本發明之實施例另外包括用於控制無脊椎害蟲之方法，其包含使土壤接觸土壤浸潤形式之液體組合物，其包含生物有效量的任何前述實施例以及本文所述任何其他實施例之化合物及其任何組合。Embodiments of the invention also include compositions in the form of a soil infiltrating liquid formulation comprising any of the foregoing examples, as well as compounds of any of the other embodiments described herein, and any combination thereof. Embodiments of the invention additionally include a method for controlling an invertebrate pest comprising a liquid composition in contact with soil in a soil infiltrated form, comprising a biologically effective amount of any of the foregoing embodiments, and compounds of any of the other embodiments described herein and Any combination of them.

本發明之實施例亦包括一種用於控制無脊椎害蟲之噴霧組合物，其包含生物有效量的任何前述實施例以及本文所述任何其他實施例之化合物及其任何組合及推進劑。本發明之實施例另外包括一種用於控制無脊椎害蟲之誘餌組合物，其包含生物有效量的任何前述實施例以及本文所述任何其他實施例之化合物及其任何組合、一或多種食物材料、視情況之引誘劑及視情況之保濕劑。本發明之實施例亦包括一種用於控制無脊椎害蟲之裝置，其包含該誘餌組合物及適合容納該誘餌組合物之外殼，其中該外殼具有至少一開口，其尺寸允許該無脊椎害蟲穿過該開口使該無脊椎害蟲可自外殼外之位置得以接近該誘餌組合物，且其中該外殼另外適合置放於或靠近無脊椎害蟲潛在或已知的活躍地點。Embodiments of the invention also include a spray composition for controlling an invertebrate pest comprising a biologically effective amount of any of the foregoing examples, as well as compounds of any of the other embodiments described herein, and any combination thereof and propellant. Embodiments of the invention additionally include a bait composition for controlling an invertebrate pest comprising a biologically effective amount of any of the foregoing embodiments, and any other embodiments of the compounds described herein, and any combination thereof, one or more food materials, Depending on the attractant and humectant as appropriate. Embodiments of the invention also include a device for controlling an invertebrate pest comprising the bait composition and an outer casing adapted to receive the bait composition, wherein the outer casing has at least one opening sized to allow the invertebrate pest to pass through The opening allows the invertebrate pest to access the bait composition from a location outside the outer casing, and wherein the outer casing is additionally adapted to be placed at or near an active or known active location of the invertebrate pest.

應注意R4 取代基之環烷基或環烯基部分為C3 －C4 碳環之式1 化合物。因此在該化合物之R4 中，"C4 －C1 2 烷基環烷基係由"(C1 －C8 烷基)(C3 －C4 環烷基)"組成"，"C5 －C1 2 烯基環烷基"係由"(C2 －C8 烯基)(C3 －C4 環烷基)"組成，"C5 －C1 2 炔基環烷基"係由"(C2 －C8 炔基)(C3 －C4 環烷基)"組成，"C4 －C1 2 環烷基烷基"係由"(C3 －C4 環烷基)(C1 －C8 烷基)"組成，"C5 －C1 2 環烷基烯基"係由"(C3 －C4 環烷基)(C2 －C8 烯基)"組成，"C5 －C1 2 環烷基炔基"係由"(C3 －C4 環烷基)(C2 －C8 炔基)"組成，"C4 －C1 2 環烯基烷基"係由"(C3 －C4 環烯基)(C1 －C8 烷基)"組成且"C4 －C1 2 烷基環烯基"係由"(C1 －C8 烷基)(C3 －C4 環烯基)"組成。It should be noted that the cycloalkyl or cycloalkenyl moiety of the R 4 substituent is a C 3 -C 4 carbocyclic compound of formula 1 . Thus, in R 4 of the compound, "C 4 -C 1 2 alkylcycloalkyl" is composed of "(C 1 -C 8 alkyl)(C 3 -C 4 cycloalkyl)","C 5 -C 1 2 alkenylcycloalkyl" consists of "(C 2 -C 8 alkenyl)(C 3 -C 4 cycloalkyl)", "C 5 -C 1 2 alkynylcycloalkyl""(C 2 -C 8 alkynyl)(C 3 -C 4 cycloalkyl)" composition, "C 4 -C 1 2 cycloalkylalkyl" is derived from "(C 3 -C 4 cycloalkyl)""C 1 -C 8 alkyl"" composition, "C 5 -C 1 2 cycloalkylalkenyl" is composed of "(C 3 -C 4 cycloalkyl)(C 2 -C 8 alkenyl)"," C 5 -C 1 2 cycloalkylalkynyl"" consists of "(C 3 -C 4 cycloalkyl)(C 2 -C 8 alkynyl)", "C 4 -C 1 2 cycloalkenylalkyl" Department of "(C 3 -C 4 cycloalkenyl) (C 1 -C 8 alkyl)" component and "C 4 -C 1 2 alkyl cycloalkenyl" line of "(C 1 -C 8 alkyl) (C 3 -C 4 cycloalkenyl)" composition.

應注意除3－溴－N －[4－氯－2－[[(環丙基甲基)胺基]羰基]－6－甲基苯基]－1－(3－氯－2－吡啶基)－1H －吡唑－5－甲醯胺以外之式1 化合物。It should be noted that 3-bromo- N- [4-chloro-2-[[(cyclopropylmethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridyl) a compound of formula 1 other than -1 H -pyrazole-5-carbamamine.

應注意包含3－溴－N －4－氯－2－[[(環丙基甲基)胺基]－羰基]－6－甲基苯基]－1－(3－氯－2－吡啶基)－1H －吡唑－5－甲醯胺及至少一種額外的生物活性化合物或藥劑之混合物。尤其應注意包含3－溴－N －[4－氯－2－[[(環丙基甲基)胺基]－羰基]－6－甲基苯基]－1－(3－氯－2－吡啶基)－1H －吡唑－5－甲醯胺及至少一種額外的生物活性化合物或藥劑之增效混合物。應另外注意包含3－溴－N －[4－氯－2－[[(環丙基甲基)胺基]－羰基]－6－甲基苯基]－1－(3－氯－2－吡啶基)－1H －吡唑－5－甲醯胺及益達胺(imidacloprid)或噻蟲嗪(thiamethoxam)之增效混合物。It should be noted that 3-bromo- N- 4-chloro-2-[[(cyclopropylmethyl)amino]-carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridyl) is included. a mixture of -1 H -pyrazole-5-carbamamine and at least one additional biologically active compound or agent. Particular attention should be paid to the inclusion of 3-bromo- N- [4-chloro-2-[[(cyclopropylmethyl)amino]-carbonyl]-6-methylphenyl]-1-(3-chloro-2- A synergistic mixture of pyridyl)-1 H -pyrazole-5-formamide and at least one additional biologically active compound or agent. Additional attention should be paid to the inclusion of 3-bromo- N- [4-chloro-2-[[(cyclopropylmethyl)amino]-carbonyl]-6-methylphenyl]-1-(3-chloro-2- A synergistic mixture of pyridyl)-1 H -pyrazole-5-formamide and imidacloprid or thiamethoxam.

應注意除3－溴－N －[4－氯－2－[[(1－環丙基乙基)胺基]羰基]－6－甲基苯基]－1－(3－氯－2－吡啶基)－1H －吡唑－5－甲醯胺以外之式1 化合物。It should be noted that in addition to 3-bromo- N- [4-chloro-2-[[(1-cyclopropylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2- A compound of formula 1 other than pyridyl)-1 H -pyrazole-5-formamide.

應注意包含3－溴－N －[4－氯－2－[[(1－環丙基乙基)胺基]－羰基]－6－甲基苯基]－1－(3－氯－2－吡啶基)－1H －吡唑－5－甲醯胺及至少一種額外的生物活性化合物或藥劑之混合物。It should be noted that 3-bromo- N- [4-chloro-2-[[(1-cyclopropylethyl)amino]-carbonyl]-6-methylphenyl]-1-(3-chloro-2) a mixture of -pyridyl)-1 H -pyrazole-5-formamide and at least one additional biologically active compound or agent.

應注意其中當J為J－1,R6 為CF3 ,R7 為3－氯－2－吡啶基，R2 及R3 為H,R1 a 為Me且R1 b 為H或Cl時，則R4 不為環丙基甲基之式1 化合物或其N －氧化物。It should be noted that when J is J-1, R 6 is CF 3 , R 7 is 3-chloro-2-pyridyl, R 2 and R 3 are H, R 1 a is Me and R 1 b is H or Cl. , wherein R 4 is not a cyclopropylmethyl compound of formula 1 or an N -oxide thereof.

應注意包含其中J為J－1,R6 為CF3 ,R7 為3－氯－2－吡啶基，R2 及R3 為H,R1 a 為Me,R1 b 為H或Cl時且R4 為環丙基甲基之式1 化合物或其N －氧化物及至少一種額外的生物活性化合物或藥劑之混合物。It should be noted that where J is J-1, R 6 is CF 3 , R 7 is 3-chloro-2-pyridyl, R 2 and R 3 are H, R 1 a is Me, and R 1 b is H or Cl. And R 4 is a cyclopropylmethyl compound of formula 1 or an N -oxide thereof and a mixture of at least one additional biologically active compound or agent.

應注意其中當J為J－1,R6 為CF3 ,R7 為3－氯－2－吡啶基，R2 及R3 為H,R1 a 為Me且R1 b 為Cl時，則R4 不為(2－甲基環丙基)甲基、(2,2－二氯－1－甲基環丙基)甲基、(1－甲基－環丙基)甲基或1－環丁基乙基之式1 化合物。It should be noted that when J is J-1, R 6 is CF 3 , R 7 is 3-chloro-2-pyridyl, R 2 and R 3 are H, R 1 a is Me and R 1 b is Cl. R 4 is not (2-methylcyclopropyl)methyl, (2,2-dichloro-1-methylcyclopropyl)methyl, (1-methyl-cyclopropyl)methyl or 1- A compound of formula 1 of cyclobutylethyl.

應注意包含其中J為J－1,R6 為CF3 ,R7 為3－氯－2－吡啶基，R2 及R3 為H,R1 a 為Me,R1 b 為Cl且R4 為(2－甲基環丙基)甲基、(2,2－二氯－1－甲基環丙基)甲基、(1－甲基－環丙基)甲基或1－環丁基乙基之式1 化合物及至少一種額外的生物活性化合物或藥劑之混合物。It should be noted that J is J-1, R 6 is CF 3 , R 7 is 3-chloro-2-pyridyl, R 2 and R 3 are H, R 1 a is Me, R 1 b is Cl and R 4 Is (2-methylcyclopropyl)methyl, (2,2-dichloro-1-methylcyclopropyl)methyl, (1-methyl-cyclopropyl)methyl or 1-cyclobutyl A mixture of a compound of formula 1 of ethyl and at least one additional biologically active compound or agent.

應注意其中當J為J－1,R6 為Br、Cl、CF3 或OCH2 CF3 ,R7 為在吡啶基環之3及/或5位置視情況經鹵素取代之2－吡啶基，R2 及R3 為H,R4 為1－環丙基乙基且R1 a 為Me、Et、鹵素、CF3 、CHF2 或OCHF2 時，則R1 b 不為H、鹵素、CF3 、CHF2 、NO2 、OMe、CH＝CH2 、CH＝CCl2 、C≡CH、C≡CI、C(O)CH3 、C(O)CF3 、C(O)OMe或C(O)Oi－Pr之式1 化合物。It should be noted that when J is J-1, R 6 is Br, Cl, CF 3 or OCH 2 CF 3 , and R 7 is a 2-pyridyl group optionally substituted by halogen at the 3 and/or 5 positions of the pyridyl ring. When R 2 and R 3 are H, R 4 is 1-cyclopropylethyl and R 1 a is Me, Et, halogen, CF 3 , CHF 2 or OCHF 2 , then R 1 b is not H, halogen, CF 3 , CHF 2 , NO 2 , OMe, CH=CH 2 , CH=CCl 2 , C≡CH, C≡CI, C(O)CH 3 , C(O)CF 3 , C(O)OMe or C( O) A compound of formula 1 of Oi-Pr.

應注意包含其中J為J－1,R6 為Br、Cl、CF3 或OCH2 CF3 ,R7 為在吡啶基環之3及/或5位置視情況經鹵素取代之2－吡啶基，R2 及R3 為H，R4 為1－環丙基乙基，R1 a 為Me、Et、鹵素、CF3 、CHF2 或OCHF2 且R1 b 為 H、鹵素、CF3 、CHF2 、NO2 、OMe、CH＝CH2 、CH＝CCl2 、C≡CH、C≡CI、C(O)CH3 、C(O)CF3 、C(O)OMe或C(O)Oi－Pr之式1 化合物及至少一種額外的生物活性化合物或藥劑之混合物。It should be noted that wherein J is J-1, R 6 is Br, Cl, CF 3 or OCH 2 CF 3 , and R 7 is a 2-pyridyl group optionally substituted by halogen at the 3 and/or 5 positions of the pyridyl ring. R 2 and R 3 are H, R 4 is 1-cyclopropylethyl, R 1 a is Me, Et, halogen, CF 3 , CHF 2 or OCHF 2 and R 1 b is H, halogen, CF 3 , CHF 2 , NO 2 , OMe, CH=CH 2 , CH=CCl 2 , C≡CH, C≡CI, C(O)CH 3 , C(O)CF 3 , C(O)OMe or C(O)Oi -Pr compound of formula 1 and at least one additional biologically active compound or mixture of agents.

應注意其中當J為J－1,R7 為視情況經取代的2－吡啶基，R1 a 為Me、Et、鹵素、CF3 、CHF2 或OCHF2 且R2 及R3 為H時，則R4 不為環丙基甲基、1－環丙基乙基、(2－甲基－環丙基)甲基、(2,2－二氯－1－甲基環丙基)甲基、(1－甲基環丙基)－甲基或1－環丁基乙基之式1 化合物或其N －氧化物。It should be noted that where J is J-1, R 7 is optionally substituted 2-pyridyl, R 1 a is Me, Et, halogen, CF 3 , CHF 2 or OCHF 2 and R 2 and R 3 are H , R 4 is not cyclopropylmethyl, 1-cyclopropylethyl, (2-methyl-cyclopropyl)methyl, (2,2-dichloro-1-methylcyclopropyl) A A compound of formula 1 or its N -oxide, (1-methylcyclopropyl)-methyl or 1-cyclobutylethyl.

應注意包含其中J為J－1,R7 為視情況經取代的2－吡啶基，R1 a 為Me、Et、鹵素、CF3 、CHF2 或OCHF2 ，R2 及R3 為H且R4 為環丙基甲基、1－環丙基乙基、(2－甲基－環丙基)甲基、(2,2－二氯－1－甲基環丙基)甲基、(1－甲基環丙基)－甲基或1－環丁基乙基之式1 化合物或其N －氧化物及至少一種額外的生物活性化合物或藥劑之混合物。It should be noted that wherein J is J-1, R 7 is optionally substituted 2-pyridyl, R 1 a is Me, Et, halogen, CF 3 , CHF 2 or OCHF 2 , and R 2 and R 3 are H and R 4 is cyclopropylmethyl, 1-cyclopropylethyl, (2-methyl-cyclopropyl)methyl, (2,2-dichloro-1-methylcyclopropyl)methyl, ( A compound of formula 1 or a N -oxide of 1-methylcyclopropyl)-methyl or 1-cyclobutylethyl and at least one additional biologically active compound or mixture of agents.

應注意其中當J為J－1,R7 為視情況經取代之2－吡啶基且R2 及R3 為H時，則R4 不為環丙基甲基、1－環丙基乙基(2－甲基環丙基)甲基、(2,2－二氯－1－甲基環丙基)甲基、(1－甲基環丙基)甲基或1－環丁基乙基之式1 化合物或其N －氧化物。It should be noted that when J is J-1, R 7 is an optionally substituted 2-pyridyl group and R 2 and R 3 are H, then R 4 is not a cyclopropylmethyl group or a 1-cyclopropylethyl group. (2-methylcyclopropyl)methyl, (2,2-dichloro-1-methylcyclopropyl)methyl, (1-methylcyclopropyl)methyl or 1-cyclobutylethyl A compound of formula 1 or an N -oxide thereof.

應注意包含其中J為J－1,R7 為視情況經取代之2－吡啶基，R2 及R3 為H且R4 為環丙基甲基、1－環丙基乙基(2－甲基環丙基)甲基、(2,2－二氯－1－甲基環丙基)甲基、(1－甲基環丙基)甲基或1－環丁基乙基之式1 化合物或其N －氧化物及至少一種額外的生物活性化合物或藥劑之混合物。It should be noted that wherein J is J-1, R 7 is optionally substituted 2-pyridyl, R 2 and R 3 are H and R 4 is cyclopropylmethyl, 1-cyclopropylethyl (2- Formula 1 of methylcyclopropyl)methyl, (2,2-dichloro-1-methylcyclopropyl)methyl, (1-methylcyclopropyl)methyl or 1-cyclobutylethyl A mixture of a compound or an N -oxide thereof and at least one additional biologically active compound or agent.

應注意其中當J為J－1,R7 為視情況經取代之2－吡啶基且R2 及R3 為H時，則R4 不為視情況經取代的(C3 －C4 環烷基)(C1 －C6 烷基)之式1 化合物或其N －氧化物。It should be noted that where J is J-1, R 7 is optionally substituted 2-pyridyl and R 2 and R 3 are H, then R 4 is not optionally substituted (C 3 -C 4 naphthenic) a compound of formula 1 (C 1 -C 6 alkyl) or an N -oxide thereof.

應注意包含其中J為J－1,R7 為視情況經取代之2－吡啶基，R2 及R3 為H且R4 為視情況經取代的(C3 －C4 環烷基)(C1 －C6 烷基)之式1 化合物或其N －氧化物及至少一種額外的生物活性化合物或藥劑之混合物。It should be noted that R is a compound wherein J is J-1, R 7 is optionally substituted 2-pyridine, R 2 and R 3 are H and R 4 is optionally substituted (C 3 -C 4 cycloalkyl) A compound of formula 1 or a N -oxide thereof of C 1 -C 6 alkyl) and at least one additional biologically active compound or agent.

應注意包含3－溴－1－(3－氯－2－吡啶基)－N －[4－氰基－2－[[(環丙基甲基)胺基]－羰基]－6－甲基苯基]－1H －吡唑－5－甲醯胺及至少一種額外的生物活性化合物或藥劑之混合物。應尤其注意包含3－溴－1－(3－氯－2－吡啶基)－N －[4－氰基－2－[[(環丙基甲基)胺基]－羰基]－6－甲基苯基]－1H －吡唑－5－甲醯胺及至少一種額外的生物活性化合物或藥劑之增效混合物。應另外注意包含3－溴－1－(3－氯－2－吡啶基)－N －[4－氰基－2－[[(環丙基甲基)－胺基]羰基]－6－甲基苯基]－1H －吡唑－5－甲醯胺及益達胺或噻蟲嗪之增效混合物。It should be noted containing 3-bromo-1- (3-chloro-2-pyridinyl) - N - [4- cyano-2 - [[(cyclopropylmethyl) amino] - carbonyl] -6-methyl A mixture of phenyl]-1 H -pyrazole-5-formamide and at least one additional biologically active compound or agent. Particular attention should comprise 3-bromo-1- (3-chloro-2-pyridinyl) - N - [4- cyano-2 - [[(cyclopropylmethyl) amino] - carbonyl] -6- A synergistic mixture of phenyl]-1 H -pyrazole-5-formamide and at least one additional biologically active compound or agent. Also note should contain 3-bromo-1- (3-chloro-2-pyridinyl) - N - [4- cyano-2 - [[(cyclopropylmethyl) - amino] carbonyl] -6- A synergistic mixture of phenyl]-1 H -pyrazole-5-metholamine and etadamine or thiamethoxam.

應注意其中當R1 a 為Me、Cl、Br或F，R1 b 為CN,R2 為H，R3 為H或Me，J為J－1，R6 為F、Cl、Br、C1 －C4 鹵烷基或C1 －C4 鹵烷氧基，R7 為在吡啶基環之3位置經F、Cl或Br(作為R9 a )取代且在5位置未經取代或在5位置經F或Cl(作為R9 b )取代的2－吡啶基時，則R4 不為C4 －C6 環烷基烷基之式1 化合物。It should be noted that when R 1 a is Me, Cl, Br or F, R 1 b is CN, R 2 is H, R 3 is H or Me, J is J-1, and R 6 is F, Cl, Br, C. 1 -C 4 haloalkyl or C 1 -C 4 haloalkoxy, R 7 is substituted at the 3 position of the pyridyl ring by F, Cl or Br (as R 9 a ) and is unsubstituted at the 5 position or When the 5-position is substituted with a 2-pyridyl group of F or Cl (as R 9 b ), then R 4 is not a compound of formula 1 of a C 4 -C 6 cycloalkylalkyl group.

應注意其中當R1 b 為CN，J為J－1，R7 為視情況經取代之2－吡啶基，R2 為H且R3 為H或Me時，則R4 不為C4 －C6 環烷基烷基之式1 化合物。It should be noted that when R 1 b is CN, J is J-1, R 7 is an optionally substituted 2-pyridyl group, R 2 is H and R 3 is H or Me, then R 4 is not C 4 - A compound of formula 1 wherein a C 6 cycloalkylalkyl group.

應注意其中當R1 b 為CN,J為J－1且R7 為視情況經取代之2－吡啶基時，則R4 不為C4 －C6 環烷基烷基之式1 化合物。It should be noted that where R 1 b is CN, J is J-1 and R 7 is optionally substituted 2-pyridyl, then R 4 is not a C 4 -C 6 cycloalkylalkyl compound of formula 1 .

應注意實例1A至2J、3A至5D、6A－6B、7A－7U、10A－10D、11A－11D、12A－12D、13A－13B、14A－14B、15A－15L之化合物及前述實施例8J及/或實施例8K之化合物的任何組合。同樣應注意實施例8J及8K之化合物與化合物3－溴－1－(3－氯－2吡啶基)－N －[4－氰基－2－[[環丙基甲基)胺基]羰基]－6－甲基苯基]－1H －吡唑－5－甲醯胺之組合。It should be noted that the compounds of Examples 1A to 2J, 3A to 5D, 6A-6B, 7A-7U, 10A-10D, 11A-11D, 12A-12D, 13A-13B, 14A-14B, 15A-15L and the foregoing Example 8J and / or any combination of the compounds of Example 8K. It should also be noted that the compound of Example 8J, and 8K of the compound 3-bromo-1- (3-chloro-2-pyridinyl) - N - [4- cyano-2 - [[cyclopropylmethyl) amino] carbonyl a combination of -6-methylphenyl]-1 H -pyrazole-5-formamide.

式1 化合物可藉由流程1－8中所描述之一或多種以下方法及變體來製備。在下式1－11 之化合物中J、R1 a 、R1 b 、R2 、R3 及R4 之定義係如以上發明內容中所定義。式3a 為式3 之子集，同樣式10a 為式10 之子集且式1a 為式1 之子集。The compound of formula 1 can be prepared by one or more of the following methods and variants as described in Schemes 1-8. The definitions of J, R 1 a , R 1 b , R 2 , R 3 and R 4 in the compounds of the following formula 1-11 are as defined in the above summary. Equation 3a is a subset of Equation 3 , and Equation 10a is a subset of Equation 10 and Equation 1a is a subset of Equation 1 .

式1 之化合物可藉由如流程1中所概述之式2 之苯幷噁嗪酮與式3 之胺反應來製備。The compound of formula 1 can be prepared by reacting a benzoxazinone of formula 2 as outlined in Scheme 1 with an amine of formula 3 .

可在無溶劑狀況下或在包括四氫呋喃、二乙醚、二氯甲烷、氯仿或諸如甲醇或乙醇之低碳醇之各種適當溶劑中運行該反應，其中最適溫度在室溫至溶劑回流溫度之範圍內。苯幷噁嗪酮與胺產生鄰胺苯甲醯胺之通用反應詳細記錄於化學文獻中。關於苯幷噁嗪酮化學之綜述參見Jakobsen等人，Bioorganic and Medicinal Chemistry 2000, 8 , 2095－2103及其中引用之參考文獻。同樣參見G.M.Coppola,J.Heterocyclic Chemistry 1999, 36, 563－588。The reaction can be carried out in the absence of a solvent or in various suitable solvents including tetrahydrofuran, diethyl ether, dichloromethane, chloroform or a lower alcohol such as methanol or ethanol, wherein the optimum temperature is in the range from room temperature to the reflux temperature of the solvent. . The general reaction of benzoxazinone with an amine to produce o-amine benzamide is detailed in the chemical literature. For a review of benzoxazinone chemistry, see Jakobsen et al, Bioorganic and Medicinal Chemistry 2000, 8 , 2095-2103 and references cited therein. See also GM Coppola, J. Heterocyclic Chemistry 1999, 36, 563-588.

式2 之苯幷噁嗪酮可藉由多種方法製備。尤其可使用的三種方法詳細敍述於流程2－4中。在流程2中，式2 之苯幷噁嗪酮直接經由使式4 之羧酸與式5 之鄰胺苯甲酸偶合來製備。The benzoxazinone of formula 2 can be prepared by a variety of methods. The three methods that can be used in particular are described in detail in Schemes 2-4. In Scheme 2, the benzoxazinone of Formula 2 is prepared directly by coupling a carboxylic acid of Formula 4 with an o-amine benzoic acid of Formula 5 .

此涉及在諸如三乙胺之三級胺存在下將甲磺醯氯相繼加入式4之吡唑羧酸中，接著加入式5之鄰胺苯甲酸，接著第二次加入三乙胺與甲磺醯氯。此方法通常提供苯幷噁嗪酮之良好產率。This involves the sequential addition of methanesulfonyl chloride to the pyrazole carboxylic acid of formula 4 in the presence of a tertiary amine such as triethylamine, followed by the addition of the o-amine benzoic acid of formula 5 followed by the second addition of triethylamine and methanesulfonate. Chlorine. This method generally provides good yields of benzoxazinone.

流程3描述式2之苯幷噁嗪酮之替代製備方法，其涉及使式7之酸氯化物與式6之靛紅酸酐偶合以直接提供式2苯幷噁嗪酮。諸如吡啶或吡啶/乙腈之溶劑適用於此反應。式7之酸氯化物可藉由諸如以亞硫醯氯或乙二醯氯氯化之已知方法自式4之對應酸獲得。Scheme 3 describes an alternative method of preparing benzoxazinone of Formula 2 which involves coupling an acid chloride of Formula 7 with a isatoic anhydride of Formula 6 to provide a benzoxazinone of Formula 2 directly. A solvent such as pyridine or pyridine/acetonitrile is suitable for this reaction. The acid chloride of formula 7 can be obtained from the corresponding acid of formula 4 by known methods such as chlorination with sulfinium chloride or ethylene chloride.

在流程4中，式2之苯幷噁嗪酮直接經由使式4之羧酸與式5之鄰胺苯甲酸偶合來製備。此涉及將諸如3－甲啶之吡啶鹼相繼加入式4之吡唑羧酸與式5之鄰胺苯甲酸之混合物中，接著加入甲磺醯氯。此方法提供苯幷噁嗪酮非常良好之產率。對於與製備式2之代表性苯幷噁嗪酮相關之另外參考文獻，可參見PCT專利公開案WO 2003/015519、2004/011447及2004/067528。式5之鄰胺苯甲酸可購得或可藉由多種已知方法獲得。In Scheme 4, the benzoxazinone of Formula 2 is prepared directly by coupling a carboxylic acid of Formula 4 with an o-amine benzoic acid of Formula 5. This involves the sequential addition of a pyridine base such as 3-methylpyridine to a mixture of the pyrazole carboxylic acid of formula 4 and the o-amine benzoic acid of formula 5, followed by the addition of methotrexate chloride. This method provides very good yields of benzoxazinone. For additional references relating to the preparation of the representative benzoxazinone of formula 2, see PCT Patent Publications WO 2003/015519, 2004/011447 and 2004/067528. The ortho-amine benzoic acid of the formula 5 is commercially available or can be obtained by various known methods.

在流程1中，當式3之胺為一級胺(R3 為H)且不可購得，例如為2－環氧丙烷基甲基胺時，式3之胺可藉由Mitsunobu反應使式8之對應醇與鄰苯二甲醯亞胺反應以產生式9之化合物來製備(流程5)。於高溫下在諸如乙醇之質子溶劑中以水合肼進行處理來產生式3a之胺。對於此項技術中已知的製備胺之範圍廣泛之方法的一般綜述，可參見Mitsunobu,O.Comprehensive Organic Synthesis；Trost,B.M.,Fleming,I.，編輯；Pergamon：Oxford,1991；第6卷，第65－101頁。對於描述製備二級胺之方法之一般綜述，可參見Salvatore,R.N.等人，Tetrahedron 2001,57,7785－7811。In Scheme 1, when the amine of formula 3 is a primary amine (R 3 is H) and is not commercially available, for example, 2-epoxypropanemethylamine, the amine of formula 3 can be subjected to the Mitsunobu reaction to give Formula 8 The corresponding alcohol is reacted with phthalimide to produce a compound of formula 9 (Scheme 5). Treatment with hydrazine hydrate in a protic solvent such as ethanol at elevated temperature produces the amine of formula 3a. For a general review of a wide range of methods for the preparation of amines known in the art, see Mitsunobu, O. Comprehensive Organic Synthesis; Trost, BM, Fleming, I., ed.; Pergamon: Oxford, 1991; Vol. 6, Pages 65-101. For a general review describing methods for preparing secondary amines, see Salvatore, RN et al, Tetrahedron 2001, 57, 7785-7811.

製備式1化合物之替代方法描述於流程6中。在此方法中，式10之醯胺直接與式4之酸偶合以產生式1之鄰胺苯甲醯胺。此方法涉及將兩當量或兩當量以上的諸如吡啶或甲啶之胺鹼加入式4之酸中，接著加入諸如甲磺醯氯之磺醯鹵。接著添加式10之醯胺導致直接偶合以產生式1之鄰胺苯甲醯胺。An alternative method of preparing a compound of formula 1 is described in Scheme 6. In this method, the indoleamine of formula 10 is directly coupled with an acid of formula 4 to produce the o-amine benzamide of formula 1. This method involves adding two or more equivalents of an amine base such as pyridine or acridine to the acid of formula 4, followed by the addition of a sulfonium halide such as methanesulfonate. Subsequent addition of the decylamine of formula 10 results in direct coupling to produce the o-amine benzylamine of formula 1.

在流程6所述之程序之後，如流程7所示，可使用一組較佳之式10a之醯胺製備一組較佳之式1a之鄰胺苯甲醯胺。Following the procedure described in Scheme 6, as shown in Scheme 7, a preferred group of o-amine benzamides of Formula 1a can be prepared using a preferred group of the amines of Formula 10a.

式10之醯胺可如流程8中所示藉由已知方法製備，該等方法涉及使式3之胺與式11之靛紅酸酐反應。The guanamine of formula 10 can be prepared by known methods as shown in Scheme 8, which involves reacting the amine of formula 3 with the isatoic anhydride of formula 11.

應認識到以上描述用於製備式1化合物之一些試劑及反應條件可能與中間物中存在的某些官能基不相容。在此等實例中，在合成中併入保護/去保護程序或官能基互換將有助於獲得所要的產物。對於熟習化學合成之技術者而言，保護基之使用及選擇為顯而易見的(例如參見Greene,T.W.；Wuts,P.G.M.Protective Groups in Organic Synthesis，第2版；Wiley：New York,1991)。熟習此項技術者將認識到在一些狀況中，如任何個別流程中所描述引入給定試劑後，可能需要執行未詳細描述的額外常規合成步驟以完成式1化合物之合成。熟習此項技術者將同樣認識到可能需要以與呈現之特定程序所示不同之次序來執行以上流程中所說明之步驟之組合以製備式1化合物。It will be appreciated that some of the reagents and reaction conditions described above for the preparation of the compounds of Formula 1 may be incompatible with certain functional groups present in the intermediate. In such instances, incorporation of a protection/deprotection procedure or functional interchange in the synthesis will aid in obtaining the desired product. The use and selection of protecting groups is apparent to those skilled in the art of chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). Those skilled in the art will recognize that in some situations, after introduction of a given reagent as described in any of the individual schemes, additional conventional synthetic procedures not described in detail may be required to complete the synthesis of the compound of Formula 1. Those skilled in the art will recognize that a combination of the steps illustrated in the above schemes may be performed in a different order than that shown for the particular procedure presented to prepare a compound of formula 1.

熟習此項技術者將同樣認識到本文描述之式1化合物及其中間物可經歷各種親電子、親核、自由基、有機金屬、氧化及還原反應以添加取代基或改質已存在之取代基。Those skilled in the art will likewise recognize that the compounds of Formula 1 and intermediates thereof described herein can undergo various electrophilic, nucleophilic, free radical, organometallic, oxidative, and reduction reactions to add substituents or to modify existing substituents. .

無需另外詳細描述，據信熟習此項技術者使用前述說明可最大程度利用本發明。因而下列實例應解釋為僅具有說明性，並非以任何方式限制本揭示內容。以四甲基矽烷之低磁場之ppm為單位報導1 H NMR光譜；"s"意謂單峰，"d"意謂雙重峰，"t"意謂三重峰，"q"意謂四重峰，"m"意謂多重峰，"dd"意謂兩組雙重峰，"dt"意謂兩組三重峰，"br s"意謂寬單峰且"br t"意謂寬三重峰。Without further elaboration, it is believed that those skilled in the <RTIgt; The following examples are therefore to be construed as illustrative only and not in any way limiting. The 1 H NMR spectrum is reported in ppm of the low magnetic field of tetramethylnonane; "s" means a single peak, "d" means a double peak, "t" means a triplet, and "q" means a quadruple peak. "m" means multiple peaks, "dd" means two sets of double peaks, "dt" means two sets of triplets, "br s" means wide single peaks and "br t" means wide triplets.

實例1Example 1

1－(3－氯－2－吡啶基)－N －[4－氰基－2－[[(環丙基甲基)胺基]羰基]－6－甲基苯基]－3－(三氟甲基)－1H －吡唑－5－甲醯胺之製備 將於乙腈(10 mL)中藉由PCT專利公開案WO2004/067528中所描述之程序製備之2－[1－(3－氯－2－吡啶基)－3－(三氟甲基)－1H－吡唑－5－基]－8－甲基－4－氧代－4H－3,1－苯幷噁嗪－6－腈(150 mg,0.35 mmol)與鹽酸環丙基甲基胺(112 mg,1.0 mmol)及三乙胺(0.145 mL,1.0 mmol)組合。將所得溶液回流加熱若干分鐘接著於周圍溫度攪拌15分鐘。添加水(10 mL)且使混合物冷卻至0℃以使固體沉澱。過濾收集固體且相繼以水及醚/己烷洗滌以提供呈白色固體狀的標題化合物(139 mg)，熔點235－236℃。 1- (3-chloro-pyridyl) - N - [4- cyano-2 - [[(cyclopropylmethyl) amino] carbonyl] -6-methylphenyl] -3- (three Preparation of fluoromethyl)-1 H -pyrazole-5-carboxamide A 2-[1-(3-) prepared in acetonitrile (10 mL) by the procedure described in PCT Patent Publication No. WO 2004/067528 Chloro-2-pyridyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-8-methyl-4-oxo-4H-3,1-phenyloxazin-6- The nitrile (150 mg, 0.35 mmol) was combined with cyclopropylmethylamine hydrochloride (112 mg, 1.0 mmol) and triethylamine (0.145 mL, 1.0 mmol). The resulting solution was heated under reflux for several minutes and then stirred at ambient temperature for 15 minutes. Water (10 mL) was added and the mixture was cooled to 0 ° C to precipitate a solid. The solid was collected by EtOAc (EtOAc) elute

1 H NMR(CDCl3 )δ 10.7(br s,1H),8.50(d,1H),7.90(d,1H),7.63(s,1H),7.61(s,1H)7.43(dd,1H),7.28(s,1H),6.35(br t,1H),3.29(dd,2H),2.26(s,3H),1.04(m,1H),0.60(m,2H),0.28(m,2H)。 1 H NMR (CDCl 3 ) δ 10.7 (br s, 1H), 8.50 (d, 1H), 7.90 (d, 1H), 7.63 (s, 1H), 7.61 (s, 1H) 7.43 (dd, 1H), 7.28 (s, 1H), 6.35 (br t, 1H), 3.29 (dd, 2H), 2.26 (s, 3H), 1.04 (m, 1H), 0.60 (m, 2H), 0.28 (m, 2H).

實例2Example 2

3－溴－N －[4－氯－2－[[(環丙基甲基)胺基]羰基]－6－甲基苯基]－1－(3－氯－2－吡啶基)－1H －吡唑－5－甲醯胺之製備 將於乙腈(10 mL)中藉由PCT專利公開案WO2003/015519中所描述之程序製備之2－[3－溴－1－(3－氯－2－吡啶基)－1H－吡唑－5－基]－6－氯－8－甲基－4H－3,1－苯幷噁嗪－4－酮(157 mg,0.35 mmol)與鹽酸環丙基甲基胺(112 mg,1.0 mmol)及三乙胺(0.145 mL,1.0 mmol)組合。將所得溶液回流加熱若干分鐘接著於周圍溫度攪拌15分鐘。添加水(10 mL)且使混合物冷卻至0℃以使固體沉澱。過濾收集固體且相繼以水及醚/己烷洗滌以提供170 mg呈白色固體狀的標題化合物，熔點172－173℃。 3-bromo- N- [4-chloro-2-[[(cyclopropylmethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-1 Preparation of H -pyrazole-5-carboxamide A 2-[3-bromo-1-(3-chloro-) prepared by the procedure described in PCT Patent Publication No. WO2003/015519 in acetonitrile (10 mL) 2-pyridyl)-1H-pyrazol-5-yl]-6-chloro-8-methyl-4H-3,1-phenyloxazin-4-one (157 mg, 0.35 mmol) and cyclopropane hydrochloride A combination of methylamine (112 mg, 1.0 mmol) and triethylamine (0.145 mL, 1.0 mmol). The resulting solution was heated under reflux for several minutes and then stirred at ambient temperature for 15 minutes. Water (10 mL) was added and the mixture was cooled to 0 ° C to precipitate a solid. The solid was collected by EtOAc (EtOAc m.)

1 H NMR(CDCl3 )δ 10.1(br s,1H),8.46(d,1H),7.85(d,1H),7.40(dd,1H),7.26(s,2H)7.07(s,1H),6.23(br t,1H),3.25(dd,2H),2.19(s,3H),1.0(m,1H),0.58(m,2H),0.26(m,2H)。 1 H NMR (CDCl 3 ) δ 10.1 (br s, 1H), 8.46 (d, 1H), 7.85 (d, 1H), 7.40 (dd, 1H), 7.26 (s, 2H) 7.07 (s, 1H), 6.23 (br t,1H), 3.25 (dd, 2H), 2.19 (s, 3H), 1.0 (m, 1H), 0.58 (m, 2H), 0.26 (m, 2H).

實例3Example 3

3－溴－N－[4－氯－2－甲基－6－[[(2－環氧丙烷基甲基)胺基]羰基]苯基]－1－(3－氯－2－吡啶基)－1H－吡唑－5－甲醯胺之製備步驟A：2－(2－環氧丙烷基甲基)－1H－異吲哚－1,3(2H)－二酮之製備 將2－羥甲基環氧丙烷(0.250 g,2.84 mmol)、鄰苯二甲醯亞胺(0.501 g,3.4 mmol)及三苯膦(0.892 g,3.4 mmol)溶解於四氫呋喃中。接著經約5分鐘添加偶氮二甲酸二異丙酯(0.659 mL,3.4 mmol)，且將溶液於室溫下攪拌兩小時。將反應混合物減壓濃縮且經由中壓液相層析(乙酸乙酯/己烷梯度)純化以提供呈淺黃色固體狀的標題化合物(0.485 g)。 3-bromo-N-[4-chloro-2-methyl-6-[[(2-epoxypropenylmethyl)amino]carbonyl]phenyl]-1-(3-chloro-2-pyridyl) Preparation of -1H-pyrazole-5-carboxamide A: Preparation of 2-(2-epoxypropenylmethyl)-1H-isoindole-1,3(2H)-dione 2- Hydroxymethyl propylene oxide (0.250 g, 2.84 mmol), phthalimide (0.501 g, 3.4 mmol) and triphenylphosphine (0.892 g, 3.4 mmol) were dissolved in tetrahydrofuran. Diisopropyl azodicarboxylate (0.659 mL, 3.4 mmol) was then added over ca. 5 min and the solution was stirred at room temperature for two hours. The reaction mixture was concentrated with EtOAc EtOAc m.

1 H NMR(CDCl3 )δ 7.86(m 2H),7.72(m 2H),5.06(m,1H),4.62(m,2H),4.08(m 1H),3.92(m 1H),2.73(m,1H),2.54(m,1H)。 1 H NMR (CDCl 3 ) δ 7.86 (m 2H), 7.72 (m 2H), 5.06 (m, 1H), 4.62 (m, 2H), 4.08 (m 1H), 3.92 (m 1H), 2.73 (m, 1H), 2.54 (m, 1H).

步驟B：3－溴－N－[4－氯－2－甲基－6－[[(2－環氧丙烷基甲基)胺基]羧基]苯基]－1－(3－氯－2－吡啶基)－1H－吡唑－5－甲醯胺之製備 向2－(2－環氧丙烷基甲基)－1H －異吲哚－1,3(2H )－二酮(意即步驟A之產物)(0.150 g,0.691 mmol)之乙醇(10 mL)溶液中添加水合肼(0.035 g,0.691 mmol)。使反應混合物回流16小時。將所得混合物經由燒結玻璃粉漏斗直接過濾至含有藉由PCT公開案WO2003/015519中所描述之程序製備的2－[3－溴－1－(3－氯－2－吡啶基)－1H －吡唑－5－基]－6－氯－8－甲基－4H －3,1－苯幷噁嗪－4－酮(0.312 g,0.691 mmol)之二氯甲烷(10 mL)溶液的燒瓶中。於室溫將反應混合物攪拌24小時。將反應物減壓濃縮且將粗產物藉由矽膠中壓液相層析(以乙酸乙酯－己烷梯度溶離)純化以提供呈白色固體狀的標題化合物(0.196 g)，即本發明之化合物，熔點95－97℃。 Step B: 3-bromo-N-[4-chloro-2-methyl-6-[[(2-epoxypropenylmethyl)amino]carboxy]phenyl]-1-(3-chloro-2 Preparation of -pyridyl)-1H-pyrazole-5-carboxamide to 2-(2-epoxypropenylmethyl)-1 H -isoindole-1,3(2 H )-dione To a solution of the product of Step A) (0.150 g, 0.691 mmol) in ethanol (10 mL), EtOAc (0.035 g, 0.6. The reaction mixture was refluxed for 16 hours. The resulting mixture was directly filtered through a sintered glass frit funnel to 2-[3-bromo-1-(3-chloro-2-pyridinyl)-1 H - which was prepared by the procedure described in PCT Publication No. WO 2003/015519. Flask of a solution of pyrazol-5-yl]-6-chloro-8-methyl- 4H- 3,1-phenyloxazin-4-one (0.312 g, 0.691 mmol) in dichloromethane (10 mL) in. The reaction mixture was stirred at room temperature for 24 hours. The reaction was concentrated under reduced pressure and the title compound was purified eluted eluted elut elut elut elut elut elut elut , melting point 95-97 ° C.

1 H NMR(CDCl3 )δ 10.1(br s,1H),8.43(m 1H),7.82(m 1H),7.35(m 1H),7.23(m,2H),7.09(br s,1H),6.84(m 1H),4.92(m,1H),4.64(m 1H),4.44(m,1H),3.67(m,1H),3.53(m,1H),2.65(m,1H),2.41(m,1H),2.14(s,3H)。 1 H NMR (CDCl 3 ) δ 10.1 (br s, 1H), 8.43 (m 1H), 7.82 (m 1H), 7.35 (m 1H), 7.23 (m, 2H), 7.09 (br s, 1H), 6.84 (m 1H), 4.92 (m, 1H), 4.64 (m 1H), 4.44 (m, 1H), 3.67 (m, 1H), 3.53 (m, 1H), 2.65 (m, 1H), 2.41 (m, 1H), 2.14 (s, 3H).

實例4Example 4

3－溴－N－[4－氯－2－[[(環丙基甲基)胺基]羰基]－6－甲基苯基]－1－(3－氯－2－吡啶基)－1H－吡唑－5－甲醯胺之替代製備方法步驟A：2－胺基－5－氯－N－(環丙基甲基)－3－甲基苯甲醯胺之製備 將藉由PCT專利公開案WO2003/015519中所描述之程序製備之6－氯－8－甲基－2H－3,1－苯幷噁嗪－2,4(1H)－二酮(1.0 g,4.74 mmol)之乙酸乙酯(300 mL)溶液加熱至回流以溶解大部分固體。使所得溶液冷卻至室溫且添加環丙基甲基胺(0.61 mL,7.1 mmol)。將混合物於室溫下攪拌隔夜。過濾且除去沉澱固體。將濾液濃縮至乾燥。將殘餘固體以己烷沖洗，過濾收集且乾燥以提供呈白色固體狀的標題化合物(0.74 g)，熔點127－128℃。 3-bromo-N-[4-chloro-2-[[(cyclopropylmethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridyl)-1H -Alternative preparation of pyrazole-5-formamide Step A: Preparation of 2-amino-5-chloro-N-(cyclopropylmethyl)-3-methylbenzamide will be patented by PCT 6-Chloro-8-methyl-2H-3,1-phenyloxazin-2,4(1H)-dione (1.0 g, 4.74 mmol) of acetic acid prepared by the procedure described in WO2003/015519 The ethyl ester (300 mL) solution was heated to reflux to dissolve most of the solid. The resulting solution was cooled to room temperature and cyclopropylmethylamine (0.61 mL, 7.1 mmol). The mixture was stirred overnight at room temperature. The precipitated solid was filtered and removed. The filtrate was concentrated to dryness. The residual solid was washed with EtOAc (EtOAc m.)

1 H NMR(DMSO－d6 )δ 8.46(br t,1H),7.43(s,1H),7.12(s,1H),6.33(b s,2H),3.08(t,2H)2.08(s,3H),1.00(m,1H),0.42(dd,2H),0.21(dd,2H)。 1 H NMR (DMSO-d 6 ) δ 8.46 (br t, 1 H), 7.43 (s, 1H), 7.12 (s, 1H), 6.33 (bs, 2H), 3.08 (t, 2H) 2.08 (s, 3H) ), 1.00 (m, 1H), 0.42 (dd, 2H), 0.21 (dd, 2H).

步驟B：3－溴－N－[4－氯－2－[[(環丙基甲基)胺基]－羰基]－6－甲基苯基]－1－(3－氯－2－吡啶基)－1H－吡唑－5－甲醯胺之製備 向藉由PCT專利公開案WO2003/015519中所描述之程序製備之3－溴－1－(3－氯－2－吡啶基)－1H －吡唑－5－羧酸(0.2 g,0.66 mmol)之乙腈(20 mL)溶液中添加3－甲啶(0.161 mL,1.66 mmol)接著添加甲磺醯氯(0.054 mL,0.70 mmol)，接著將混合物於室溫下攪拌10分鐘。此時間後添加2－胺基－5－氯－N －(環丙基甲基)－3－甲基苯甲醯胺(0.158 g,0.66 mmol)且將混合物於室溫下攪拌2小時。將反應混合物以乙酸乙酯稀釋且以1 N HCl接著以飽和NaCl水溶液洗滌。將有機相經硫酸鎂乾燥且濃縮。將殘餘固體經矽膠層析純化以提供呈白色固體狀的標題化合物(0.100 g)，即本發明之化合物，熔點166－168℃。光譜資料與實例2一致。 Step B: 3-Bromo-N-[4-chloro-2-[[(cyclopropylmethyl)amino]-carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridine Preparation of -1H-pyrazole-5-carboxamide A 3-bromo-1-(3-chloro-2-pyridyl)-1 prepared by the procedure described in PCT Patent Publication No. WO2003/015519 Add 3-methylpyridine (0.161 mL, 1.66 mmol) to a solution of H -pyrazole-5-carboxylic acid (0.2 g, 0.66 mmol) in EtOAc (20 mL). The mixture was then stirred at room temperature for 10 minutes. After this time, 2-amino-5-chloro- N- (cyclopropylmethyl)-3-methylbenzamide (0.158 g, 0.66 mmol) was added and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate and washed with 1N EtOAc then brine. The organic phase was dried over magnesium sulfate and concentrated. The residue was purified by EtOAc EtOAc (EtOAc) The spectral data is consistent with Example 2.

實例5Example 5

3－溴－N－[4－氯－2－[[(1－環丙基乙基)胺基]羰基]－6－甲基苯基]－1－(3－氯－2－吡啶基)－1H－吡唑－5－甲醯胺之製備步驟A：1－環丙基乙酮肟之製備 將1－環丙基乙酮(Aldrich,6.55 g,78 mmol)、鹽酸羥胺(7.86 g,113.1 mmol)及乙酸鈉(9.92 g,121.7 mmol)於乙醇(50 mL)中之混合物回流加熱16小時。接著將反應物在碳酸氫鈉水溶液與乙酸乙酯之間分溶。將有機溶液以水洗滌，經硫酸鎂乾燥且過濾。濃縮濾液以提供呈澄清無色油狀的標題化合物(5.8 g)。1 H NMR指示其為E 及Z 異構體之混合物。1 H NMR(CDCl3 )δ 8.9(br s,1H),2.44及1.60(2 m,1H),1.72及1.55(2 s,3H),0.85及0.74(2 m,4H)。 3-bromo-N-[4-chloro-2-[[(1-cyclopropylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl) Preparation of -1H-pyrazole-5-carboxamide A: Preparation of 1-cyclopropylethanone oxime 1-Cyclopropylethanone (Aldrich, 6.55 g, 78 mmol), hydroxylamine hydrochloride (7.86 g, A mixture of 113.1 mmol) and sodium acetate (9.92 g, 121.7 mmol) in ethanol (50 mL) The reaction was then partitioned between aqueous sodium bicarbonate and ethyl acetate. The organic solution was washed with water, dried over magnesium sulfate and filtered. The filtrate was concentrated to give the title compound (5.8 g). 1 H NMR indicated it was a mixture of the E and Z isomers. 1 H NMR (CDCl 3 ) δ 8.9 (br s, 1H), 2.44 and 1.60 (2 m, 1H), 1.72 and 1.55 (2 s, 3H), 0.85 and 0.74 (2 m, 4H).

步驟B：α－甲基環丙烷甲胺之製備 向1－環丙基乙酮肟(意即步驟A之產物，0.5 g,5.0 mmol)之二乙醚(10 mL)溶液中添加1.0 M氫化鋰鋁之二乙醚(5.0 mL,5.0 mmol)溶液，且將反應混合物於室溫下攪拌30分鐘。接著將混合物加熱至回流歷經額外8小時。使反應混合物冷卻且藉由相繼逐滴添加水(1.0 mL)、15% NaOH水溶液(1.0 mL)及水(3.0 mL)來終止反應。將醚層自水層傾析，且將水層另外以二乙醚萃取兩次。將醚萃取物經硫酸鎂乾燥且過濾以提供16 mL標題胺於醚中之儲備溶液，其直接用於步驟C中。 Step B: Preparation of α-Methylcyclopropane Methylamine To a solution of 1-cyclopropylethanone oxime (meaning product of Step A, 0.5 g, 5.0 mmol) in diethyl ether (10 mL) A solution of aluminum diethyl ether (5.0 mL, 5.0 mmol) was obtained and the mixture was stirred at room temperature for 30 min. The mixture was then heated to reflux for an additional 8 hours. The reaction mixture was cooled and the reaction was quenched by successively water (1.0 mL), 15% aqueous NaOH (1.0 mL) and water (3.0 mL). The ether layer was decanted from the aqueous layer and the aqueous layer was extracted twice with diethyl ether. The ether extract was dried over MgSO.sub.4 and filtered to afford 16 <RTIgt;

步驟C：3－溴－N－[4－氯－2－[[(1－環丙基乙基)胺基]羰基]－6－甲基苯基]－1－(3－氯－2－吡啶基)－1H－吡唑－5－甲醯胺之製備 將藉由PCT專利公開案WO2003/015519中所描述之程序製備之2－[3－溴－1－(3－氯－2－吡啶基)－1H －吡唑－5－基]－6－氯－8－甲基－4H －3,1－苯幷噁嗪－4－酮(0.080 g,0.18 mmol)之乙腈(5 mL)溶液與含有過量α－甲基環丙烷甲胺(意即步驟B之產物)之醚溶液(6 mL)組合。將所得混合物加熱至回流歷經若干分鐘接著於室溫下攪拌隔夜。將反應混合物濃縮，且將固體經矽膠層析純化以提供呈白色固體狀的標題化合物(0.027 g)，即本發明之化合物，熔點182－183℃。 Step C: 3-Bromo-N-[4-chloro-2-[[(1-cyclopropylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2- Preparation of pyridyl)-1H-pyrazole-5-carboxamide A 2-[3-bromo-1-(3-chloro-2-pyridine) prepared by the procedure described in PCT Patent Publication WO2003/015519 yl) -1 H - pyrazol-5-yl] -6-chloro-8-methyl-phenyl -4 H -3,1- Bing oxazin-4-one (0.080 g, 0.18 mmol) of acetonitrile (5 mL The solution was combined with an ether solution (6 mL) containing an excess of α-methylcyclopropane methylamine (ie, the product of Step B). The resulting mixture was heated to reflux for several minutes then stirred at room temperature overnight. The reaction mixture was concentrated, and EtOAc EtOAc m.

1 H NMR(CDCl3 )δ 10.15(s,1H),8.48(d,1H),7.83(d,1H),7.38(m,1H),7.26(m,2H)7.03(s,1H),6.08(d,1H),3.50(m,1H),2.19(s,3H),1.27(d,3H),0.88(m,1H),0.57(m,1H),0.46(m,1H),0.37(m,1H),0.27(m,1H)。 1 H NMR (CDCl 3 ) δ 10.15 (s, 1H), 8.48 (d, 1H), 7.83 (d, 1H), 7.38 (m, 1H), 7.26 (m, 2H) 7.03 (s, 1H), 6.08 (d, 1H), 3.50 (m, 1H), 2.19 (s, 3H), 1.27 (d, 3H), 0.88 (m, 1H), 0.57 (m, 1H), 0.46 (m, 1H), 0.37 ( m, 1H), 0.27 (m, 1H).

實例6Example 6

3－溴－1－(3－氯－2－吡啶基)－N－[4－氰基－2－[[(1－環丙基乙基)胺基]羰基]－6－甲基苯基]－1H－吡唑－5－甲醯胺之製備 將藉由PCT專利公開案WO2004/067528中所描述之程序製備之2－[3－溴－1－(3－氯－2－吡啶基)－1H －吡唑－5－基]－8－甲基－4－氧代－4H －3,1－苯幷噁嗪－6－腈(0.200 g,0.45 mmol)於乙腈(25 mL)中之混合物加溫以形成均質溶液，接著將其與含有過量α－甲基環丙烷甲胺(意即實例5步驟B之產物)之醚溶液(4 mL)組合。將所得混合物於周圍溫度下攪拌20分鐘。將反應混合物濃縮，且將固體殘餘物懸浮於二乙醚中，且過濾收集以提供呈固體狀的標題化合物(0.099 g)，即本發明之化合物，熔點244－245℃。 3-bromo-1-(3-chloro-2-pyridyl)-N-[4-cyano-2-[[(1-cyclopropylethyl)amino]carbonyl]-6-methylphenyl Preparation of -1H-pyrazole-5-carboxamide A 2-[3-bromo-1-(3-chloro-2-pyridyl) prepared by the procedure described in PCT Patent Publication No. WO 2004/067528 -1 H -pyrazol-5-yl]-8-methyl-4-oxo-4 H -3,1-phenyloxazin-6-carbonitrile (0.200 g, 0.45 mmol) in acetonitrile (25 mL) The mixture was warmed to form a homogeneous solution which was then combined with an ethereal solution (4 mL) containing an excess of &lt;RTI ID=0.0&gt;&gt; The resulting mixture was stirred at ambient temperature for 20 minutes. The reaction mixture was concentrated, and the title compound was crystalljjjjjjjjjjjj

1 H NMR(CDCl3 )δ 10.06(s,1H),8.48(d,1H),7.86(m,1H),7.60(d,2H),7.41(m,1H),7.05(s,1H),6.20(d,1H),3.49(m,1H),2.24(s,3H),1.31(d,3H),0.89(m,1H),0.60(m,1H),0.50(m,1H),0.38(m,1H),0.32(m,1H)。 1 H NMR (CDCl 3 ) δ 10.06 (s, 1H), 8.48 (d, 1H), 7.86 (m, 1H), 7.60 (d, 2H), 7.41 (m, 1H), 7.05 (s, 1H), 6.20(d,1H), 3.49(m,1H), 2.24(s,3H), 1.31(d,3H),0.89(m,1H),0.60(m,1H),0.50(m,1H),0.38 (m, 1H), 0.32 (m, 1H).

實例7Example 7

3－溴－N－[4－氯－2－[[(1－環丙基乙基)胺基]羰基]－6－甲基苯基]－1－(2－氯苯基)－1H－吡唑－5－甲醯胺之製備步驟A：[(2E)－[(2－氯苯基)亞肼基]乙酸之製備 於室溫向鹽酸2－氯苯肼(18.8 g,0.105 mol)之水(300 mL)溶液中添加濃鹽酸(13.2 g,0.136 mol)，接著經20分鐘逐滴添加50%乙醛酸(17.1 g,0.115 mol)以形成濃稠沉澱。接著將反應混合物攪拌30分鐘。過濾分離產物，以水洗滌接著將其溶解於乙酸乙酯(400 mL)中。將所得溶液經乾燥(MgSO4 )且減壓濃縮以提供呈棕褐色固體狀的標題產物(20.5 g)。 3-bromo-N-[4-chloro-2-[[(1-cyclopropylethyl)amino]carbonyl]-6-methylphenyl]-1-(2-chlorophenyl)-1H- Preparation of pyrazole-5-formamide A: Preparation of [(2E)-[(2-chlorophenyl)indenyl]acetic acid to 2-chlorophenylhydrazine hydrochloride (18.8 g, 0.105 mol) at room temperature Concentrated hydrochloric acid (13.2 g, 0.136 mol) was added to the solution of water (300 mL), followed by dropwise addition of 50% glyoxylic acid (17.1 g, 0.115 mol) over 20 minutes to form a thick precipitate. The reaction mixture was then stirred for 30 minutes. The product was isolated by filtration, washed with water then ethyl acetate (400 mL). The resulting solution was dried (MgSO 4) and concentrated under reduced pressure to provide a tan solid title product (20.5 g).

1 H NMR(DMSO－d6 )δ 12.45(s,1H),10.7(s,1H),7.59(d,1H),7.54(s,1H),7.40(d,1H),7.23(t,1H),6.98(t,1H)。 1 H NMR (DMSO-d 6 ) δ 12.45 (s, 1H), 10.7 (s, 1H), 7.59 (d, 1H), 7.54 (s, 1H), 7.40 (d, 1H), 7.23 (t, 1H) ), 6.98 (t, 1H).

步驟B：(2－氯苯基)甲醯亞肼醯二溴之製備 於0℃向(2E )－[(2－氯苯基)亞肼基]乙酸(意即步驟A之產物)(20.5 g,0.103 mol)之N ,N －二甲基甲醯胺(188 mL)溶液中經30分鐘逐份添加N －溴代丁二醯亞胺(35.7 g,0.206 mol)。將所得混合物於周圍溫度下攪拌隔夜。將反應混合物以水(150 mL)稀釋且以二乙醚(3×200 mL)萃取。將經組合有機萃取物乾燥(MgSO4 )且經矽膠層析純化以提供呈紅色油狀的標題化合物(12.0 g)。 Step B: Preparation of (2-chlorophenyl)carboxamidine dibromide to ( 2E )-[(2-chlorophenyl)indenyl]acetic acid (meaning the product of Step A) at 0 °C ( 20.5 g, 0.103 mol) of N , N -dimethylformamide (188 mL) was added N -bromosuccinimide (35.7 g, 0.206 mol) portionwise over 30 min. The resulting mixture was stirred overnight at ambient temperature. The reaction mixture was diluted with water (150 mL) andEtOAcEtOAc. The combined organic extracts were dried (MgSO 4) and purified by chromatography on silica gel to provide the title compound as a red oil (12.0 g).

1 H NMR(CDCl3 )δ 8.15(br d,1H),7.41(d,1H),7.31(d,1H),7.21(d,1H),6.90(d,1H)。 1 H NMR (CDCl 3 ) δ 8.15 (brd, 1H), 7.41 (d, 1H), 7.31 (d, 1H), 7.21. (d, 1H), 6.90 (d, 1H).

步驟C：3－溴－1－(2－氯苯基)－4.5－二氫－1H－吡唑－5－甲酸甲酯之製備 向(2－氯苯基)甲醯亞肼醯二溴(意即步驟B之產物)(12.0 g,38.5 mmol)之N ,N －二甲基甲醯胺(110 mL)溶液中添加1份丙烯酸甲酯(13.85 mL,153.8 mmol)，接著經15分鐘逐滴添加N ,N －二異丙基乙胺(7.38 mL,42.3 mmol)。接著將反應混合物於周圍溫度下攪拌1 h。將反應混合物以水(200 mL)稀釋且以二乙醚(2×200 mL)萃取。將經組合萃取物以水及鹽水洗滌。將醚萃取物乾燥(MgSO4 )且減壓濃縮以提供標題化合物(12.2 g)。 Step C: Preparation of methyl 3-bromo-1-(2-chlorophenyl)-4.5-dihydro-1H-pyrazole-5-carboxylate to (2-chlorophenyl)carboxamidine dibromide ( Add 1 part of methyl acrylate (13.85 mL, 153.8 mmol) to a solution of N , N -dimethylformamide (110 mL) in the product of Step B) (12.0 g, 38.5 mmol), followed by 15 min. N , N -Diisopropylethylamine (7.38 mL, 42.3 mmol) was added dropwise. The reaction mixture was then stirred at ambient temperature for 1 h. The reaction mixture was diluted with water (200 mL) andEtOAcEtOAc. The combined extracts were washed with water and brine. The ether extracts were dried (MgSO 4), and to afford the title compound (12.2 g) and concentrated under reduced pressure.

1 H NMR(CDCl3 )δ 7.4(t,1H),7.34(d,1H),7.21(d,1H),7.1(t,1H),5.2(m,1H),3.55(s,3H),3.4(m,1H)。 1 H NMR (CDCl 3 ) δ 7.4 (t, 1H), 7.34 (d, 1H), 7.21 (d, 1H), 7.1 (t, 1H), 5.2 (m, 1H), 3.55 (s, 3H), 3.4 (m, 1H).

步驟D：3－溴－1－(2－氯苯基)－1H－吡唑－5－甲酸甲酯之製備 向3－溴－1－(2－氯苯基)－4,5－二氫－1H －吡唑－5－甲酸甲酯(意即步驟C之產物)(12.2 g,38.4 mmol)之丙酮(400 mL)溶液中以每10分鐘約1－公克之部分添加高錳酸鉀(24.2 g,153.6 mmol)，同時維持反應溫度低於40℃。接著將反應混合物於周圍溫度下攪拌隔夜。將反應混合物經由Celite矽藻土助濾劑過濾以移除固體，接著以二乙醚(4×100 mL)洗滌。移除溶劑後，將粗產物經由矽膠層析純化以提供呈油狀的標題化合物(5.8 g)，使其靜置固化。 Step D: Preparation of methyl 3-bromo-1-(2-chlorophenyl)-1H-pyrazole-5-carboxylate to 3-bromo-1-(2-chlorophenyl)-4,5-dihydro -1 H -pyrazole-5-carboxylic acid methyl ester (meaning product of step C) (12.2 g, 38.4 mmol) in acetone (400 mL) was added potassium permanganate in a portion of about 1-g every 10 minutes. (24.2 g, 153.6 mmol) while maintaining the reaction temperature below 40 °C. The reaction mixture was then stirred overnight at ambient temperature. Pass the reaction mixture through Celite The diatomaceous earth filter aid was filtered to remove the solid, followed by washing with diethyl ether (4 x 100 mL). After the solvent was removed, the crude material was purified eluting eluting eluting eluting eluting

1 H NMR(CDCl3 )δ 7.5(d,1H),7.4－7.5(m,3H),7.01(s,1H),3.784(s,3H)。 1 H NMR (CDCl 3 ) δ 7.5 (d, 1H), 7.4-7.5 (m, 3H), 7.01 (s, 1H), 3.784 (s, 3H).

步驟E：3－溴－1－(2－氯苯基)－1H－吡唑－5－甲酸之製備 向3－溴－1－(2－氯苯基)－1H －吡唑－5－甲酸甲酯(意即步驟D之產物)(5.8 g,18.4 mmol)之甲醇(40 mL)溶液中添加12%氫氧化鈉水溶液(8.8 g,30.5 mmol)。於周圍溫度下將反應混合物攪拌2 h。接著將反應混合物以水(100 mL)稀釋且以二乙醚(2×75 mL)洗滌。將水溶液以濃鹽酸酸化至pH 2接著以乙酸乙酯(3×150 mL)萃取。將經組合乙酸乙酯萃取物乾燥(MgSO4 )且減壓濃縮以提供標題化合物(5.8 g)。 Step E: Preparation of 3-bromo-1-(2-chlorophenyl)-1H-pyrazole-5-carboxylic acid To 3-bromo-1-(2-chlorophenyl)-1 H -pyrazole-5- A solution of methyl formate (i.e., the product of Step D) (5.8 g, 18.4 mmol) in methanol (40 mL). The reaction mixture was stirred at ambient temperature for 2 h. The reaction mixture was then diluted with water (100 mL) andEtOAc. The aqueous solution was acidified to pH 2 with cone. EtOAc then EtOAc (EtOAc) The combined ethyl acetate extracts were dried (MgSO 4), and to afford the title compound (5.8 g) and concentrated under reduced pressure.

1 H NMR(CDCl3 )δ 7.4－7.55(m,4H),7.1(s,1H)。 1 H NMR (CDCl 3 ) δ 7.4-7.55 (m, 4H), 7.1 (s, 1H).

步驟F：2－[3－溴－1－(2－氯苯基)－1H－吡唑－5－基]－6－氯－8－甲基－4H－3,1－苯幷噁嗪－4－酮之製備 將3－溴－1－(2－氯苯基)－1H －吡唑－5－甲酸(意即步驟E之產物)(0.165 g,0.55 mmol)、2－胺基－3－甲基－5－氯苯甲酸(0.101 g,0.55 mmol)及3－甲啶(0.277 mL,2.8 mmol)與乙腈(10 mL)組合且冷卻至－10℃。接著逐滴添加甲磺醯氯(0.11 mL,1.4 mmol)之乙腈(5 mL)溶液，且於周圍溫度下將反應混合物攪拌隔夜。向混合物中逐滴添加水(10 mL)以使固體沉澱。過濾收集固體，相繼以水及己烷洗滌，接著在氮氣下乾燥以提供呈白色固體狀的標題化合物(0.216 g)。 Step F: 2-[3-Bromo-1-(2-chlorophenyl)-1H-pyrazol-5-yl]-6-chloro-8-methyl-4H-3,1-phenyloxazin- Preparation of 4-ketone 3-Bromo-1-(2-chlorophenyl)-1 H -pyrazole-5-carboxylic acid (meaning the product of Step E) (0.165 g, 0.55 mmol), 2-amino- 3-Methyl-5-chlorobenzoic acid (0.101 g, 0.55 mmol) and 3-methylpyridine (0.277 mL, 2.8 mmol) were combined with acetonitrile (10 mL) and cooled to -10 °C. A solution of methanesulfonium chloride (0.11 mL, 1.4 mmol) in EtOAc (5 mL) was then evaporated, and the mixture was stirred overnight at ambient temperature. Water (10 mL) was added dropwise to the mixture to precipitate a solid. The solid was collected by EtOAc (EtOAc)EtOAc.

1 H NMR(DMSO－d6 )δ 7.90(d,1H),7.73(m,2H),7.6(m,3H),7.48(s,1H),1.73(s,3H)。 1 H NMR (DMSO-d 6 ) δ 7.90 (d, 1H), 7.73 (m, 2H), 7.6 (m, 3H), 7.48 (s, 1H), 1.73 (s, 3H).

步驟G：3－溴－N－[4－氯－2－[[(1－環丙基乙基)胺基]羰基]－6－甲基苯基]－1－(2－氯苯基)－1H－吡唑－5－甲醯胺之製備 將2－[3－溴－1－(2－氯苯基)－1H －吡唑－5－基]－6－氯－8－甲基－4H －3,1－苯幷噁嗪－4－酮(意即步驟F之產物)(0.080 g,0.18 mmol)之乙腈(20 mL)溶液與含有過量α－甲基環丙烷甲胺(意即實例5步驟B之產物)之醚溶液(5 mL)組合。將所得混合物加熱至回流歷經若干分鐘接著於室溫下攪拌隔夜。將反應混合物濃縮，且將固體殘餘物懸浮於二乙醚中，且過濾收集以提供呈固體狀的標題化合物(0.035 g)，即本發明之化合物，熔點180－181℃。 Step G: 3-Bromo-N-[4-chloro-2-[[(1-cyclopropylethyl)amino]carbonyl]-6-methylphenyl]-1-(2-chlorophenyl) Preparation of -1H-pyrazole-5-carboxamide A 2-[3-bromo-1-(2-chlorophenyl)-1 H -pyrazol-5-yl]-6-chloro-8-methyl group a solution of -4 H -3,1-phenyloxazin-4-one (meaning the product of Step F) (0.080 g, 0.18 mmol) in acetonitrile (20 mL) with excess of &lt;RTI ID=0.0&gt; This is the combination of the ether solution (5 mL) of the product of Example 5, Step B). The resulting mixture was heated to reflux for several minutes then stirred at room temperature overnight. The reaction mixture was concentrated, and the title compound was crystalljjjjjjjjjjjjjjjj

1 H NMR(CDCl3 )δ 10.03(s,1H),7.49(m,1H),7.42(m,1H),7.381(m,2H),7.26(s,1H),7.23(s,1H),7.041(s,1H),6.10(d,1H),3.47(m,1H),2.184(s,3H),1.27(d,3H),0.84(m,1H),0.54(m,1H),0.46(m,1H),0.35(m,1H),0.29(m,1H)。 1 H NMR (CDCl 3 ) δ 10.03 (s, 1H), 7.49 (m, 1H), 7.42 (m, 1H), 7.381 (m, 2H), 7.26 (s, 1H), 7.23 (s, 1H), 7.041(s,1H),6.10(d,1H), 3.47(m,1H), 2.184(s,3H), 1.27(d,3H),0.84(m,1H),0.54(m,1H),0.46 (m, 1H), 0.35 (m, 1H), 0.29 (m, 1H).

實例8Example 8

3－溴－N－[4－氯－2－甲基－6－[[(1－甲基環丙基)胺基]羰基]－苯基]－1－(3－氯－2－吡啶基)－1H－吡唑－5－甲醯胺之製備 將(1－甲基環丙基)胺基甲酸1,1－二甲基乙酯(0.300 g,1.75 mmol)與0.5 mL三氟乙酸之混合物於室溫下攪拌隔夜。向混合物中添加乙腈(15 mL)，接著添加2－[3－溴－1－(3－氯－2－吡啶基)－1H －吡唑－5－基]－6－氯－8－甲基－4H －3,1－苯幷噁嗪－4－酮(0.200 g,0.44 mmol)及三乙胺(0.400 mL,2.86 mmol)。接著將反應混合物回流加熱2 h接著冷卻至室溫。過濾收集沉澱固體，且以二乙醚及己烷洗滌以提供呈固體狀的標題化合物(0.056 g)，即本發明之化合物，熔點大於250℃。 3-bromo-N-[4-chloro-2-methyl-6-[[(1-methylcyclopropyl)amino]carbonyl]-phenyl]-1-(3-chloro-2-pyridyl) Preparation of -1H-pyrazole-5-carboxamide A 1,1-dimethylethyl (1-methylcyclopropyl)carbamate (0.300 g, 1.75 mmol) and 0.5 mL of trifluoroacetic acid The mixture was stirred overnight at room temperature. To the mixture was added acetonitrile (15 mL) followed by 2-[3-bromo-1-(3-chloro-2-pyridyl)-1 H -pyrazol-5-yl]-6-chloro-8- Base- 4H- 3, 1-phenyloxazin-4-one (0.200 g, 0.44 mmol) and triethylamine (0.400 mL, 2.86 mmol). The reaction mixture was then heated at reflux for 2 h then cooled to room temperature. The precipitated solid was collected by EtOAc (EtOAc) elute

1 H NMR(CDCl3 )δ 10.15(s,1H),8.45(d,1H),7.83(d,1H),7.39(m,1H),7.20(d,1H),7.12(d,1H),6.43(s,1H),2.16(s,3H),1.42(s,3H),0.78(m,2H),0.75(m,2H)。 1 H NMR (CDCl 3 ) δ 10.15 (s, 1H), 8.45 (d, 1H), 7.83 (d, 1H), 7.39 (m, 1H), 7.20 (d, 1H), 7.12 (d, 1H), 6.43 (s, 1H), 2.16 (s, 3H), 1.42 (s, 3H), 0.78 (m, 2H), 0.75 (m, 2H).

可藉由本文描述之程序連同此項技術中已知的方法，製備表1至10中之以下化合物。如下表中使用以下縮寫：CN意謂氰基，2－Cl－Ph意謂2－氯苯基且3－Cl－2－Py意謂3－氯－2－吡啶基。The following compounds in Tables 1 to 10 can be prepared by the procedures described herein in conjunction with methods known in the art. The following abbreviations are used in the following tables: CN means cyano, 2-Cl-Ph means 2-chlorophenyl and 3-Cl-2-Py means 3-chloro-2-pyridyl.

J係選自由以下物質組成之群： The J series is selected from the group consisting of:

J係選自由以下物質組成之群： The J series is selected from the group consisting of:

J係選自由以下物質組成之群： The J series is selected from the group consisting of:

J係選自由以下物質組成之群： The J series is selected from the group consisting of:

J係選自由以下物質組成之群： The J series is selected from the group consisting of:

J係選自由以下物質組成之群： The J series is selected from the group consisting of:

表10列出特定之式10 之醯胺，根據流程6及7之方法其可用作製備式1 及1a 化合物之中間物。Table 10 lists specific indoleamines of formula 10 which can be used as intermediates in the preparation of compounds of formula 1 and 1a according to the procedures of Schemes 6 and 7.

調配物/用途Formulation / use

本發明之化合物一般而言可以具有適於農藝或非農藝用途之載劑之調配物或組合物的形式使用，其包含液體稀釋劑、固體稀釋劑或界面活性劑中至少一者。調配物或組合物成份係經過選擇以使其與活性成份之物理性質、應用模式及諸如土壤類型、濕度及溫度之環境因素一致。可用的調配物包括諸如溶液(包括可乳化濃縮物)、懸浮液、乳液(包括微粒乳液及/或懸浮乳液)及其類似物之液體，其視情況可增稠為凝膠。可用的調配物亦包括諸如粉劑、散劑、顆粒、丸劑、錠劑、薄膜(包括種子處理)及其類似物之固體，其可分散於水("可濕的")或可溶於水。活性成份可經(微)封囊且另外形成為懸浮液或固體調配物；或活性成份之整體調配物可經封囊(或"經包衣包覆")。封囊可控制或延緩活性成份之釋放。本發明之組合物視情況亦可包含植物營養素，例如一種肥料組合物，其包含至少一種選自氮、磷、鉀、硫、鈣、鎂、鐵、銅、硼、錳、鋅及鉬之植物營養素。應注意包含至少一種肥料組合物(其至少包含一種選自氮、磷、鉀、硫、鈣及鎂之植物營養素)之組合物。另包含至少一種植物營養素之本發明之組合物可呈液體或固體形式。應注意呈顆粒、小桿或錠劑形式之固體調配物。包含肥料組合物之固體調配物可如下般製得：藉由將含有肥料組合物之本發明化合物或組合物與調配物成份混合，然後藉由諸如顆粒化或擠壓之方法製備調配物。或者固體調配物可藉由將溶於揮發性溶劑中之本發明化合物或組合物的溶液或懸浮液噴霧至預先製得呈空間穩定混合物形式之肥料組合物(諸如顆粒、小桿或錠劑)上，然後蒸發溶劑的方式來製備。可將可噴霧之調配物擴散於合適介質中且以每公頃約一至數百升之噴霧體積使用之。高濃度組合物主要可用作另外調配物之中間物。The compounds of the present invention can generally be used in the form of a formulation or composition having a carrier suitable for agronomic or non-agronomic use, comprising at least one of a liquid diluent, a solid diluent or a surfactant. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, the mode of application, and environmental factors such as soil type, humidity, and temperature. Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions), and the like, which may optionally be thickened into a gel. Useful formulations also include solids such as powders, powders, granules, pills, troches, films (including seed treatments) and the like, which may be dispersed in water ("wettable") or soluble in water. The active ingredient may be (micro)encapsulated and additionally formed into a suspension or solid formulation; or the overall formulation of the active ingredient may be encapsulated (or "coated"). The capsule can control or delay the release of the active ingredient. The composition of the invention may optionally also comprise a phytonutrient, such as a fertilizer composition comprising at least one plant selected from the group consisting of nitrogen, phosphorus, potassium, sulfur, calcium, magnesium, iron, copper, boron, manganese, zinc and molybdenum. Nutrients. Attention should be directed to compositions comprising at least one fertilizer composition comprising at least one phytonutrient selected from the group consisting of nitrogen, phosphorus, potassium, sulfur, calcium and magnesium. Compositions of the invention further comprising at least one phytonutrient may be in liquid or solid form. Attention should be paid to solid formulations in the form of granules, sticks or lozenges. A solid formulation comprising a fertilizer composition can be prepared by mixing a compound or composition of the invention comprising a fertilizer composition with a formulation and then preparing the formulation by methods such as granulation or extrusion. Or a solid formulation may be prepared by spraying a solution or suspension of a compound or composition of the invention dissolved in a volatile solvent to a fertilizer composition (such as a granule, pellet or lozenge) previously prepared in the form of a sterically stable mixture. It is prepared by evaporating the solvent. The sprayable formulation can be dispersed in a suitable medium and used in a spray volume of from about one to several hundred liters per hectare. High concentration compositions are primarily useful as intermediates in additional formulations.

該等調配物一般將含有以下大致範圍內(合計100重量%)之有效劑量之活性成份、稀釋劑及界面活性劑。These formulations will generally contain an effective amount of the active ingredient, diluent and surfactant in the broad range (100% by weight in total).

典型的固體稀釋劑係描述於Watkins等人，Handbook of Insecticide Dust Diluents and Carriers ，第2版，Dorland Books,Caldwell,New Jersey中。典型的液體稀釋劑係描述於Marsden,Solvents Guide ，第2版，Interscience,New York,1950與McCutcheon's Detergents and Emulsifiers Annual ,Allured Publ.Corp.,Ridgewood,New Jersey中，同時於Sisely與wood,Encyclopedia of Surface Active Agents ,Chemical Publ.Co.,Inc.,New York,1964中列出界面活性劑且推薦用途。所有調配物可含有少量添加劑以減少泡沫、結塊、腐蝕、微生物生長及其類似情況，或含有增稠劑以增加黏度。Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers , 2nd Edition, Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide , 2nd Edition, Interscience, New York, 1950 and McCutcheon's Detergents and Emulsifiers Annual , Allured Publ. Corp., Ridgewood, New Jersey, and Sisely and Wood, Encyclopedia of Surfactants are listed in Surface Active Agents , Chemical Publ. Co., Inc., New York, 1964 and are recommended for use. All formulations may contain small amounts of additives to reduce foaming, caking, corrosion, microbial growth and the like, or thickeners to increase viscosity.

界面活性劑包括(例如)聚乙氧基化醇、聚乙氧基化烷基酚、聚乙氧基化山梨糖醇脂肪酸酯、磺基琥珀酸二烷基酯、烷基硫酸酯、苯磺酸烷基酯、有機聚矽氧、N,N－二烷基牛磺酸酯、磺酸木質素、萘磺酸甲醛縮合物、聚羧酸酯、甘油酯、聚氧乙烯/聚氧丙稀嵌段共聚物及烷基多糖苷，其葡萄糖單位數量(係指聚合程度(D.P.))可在1至3之範圍內且烷基單位可在C6 －C1 4 之範圍內(見Pure and Applied Chemistry 72 ,1255－1264)。固體稀釋劑包括(例如)諸如膨潤土、微晶高嶺石、矽鎂土及高嶺土之黏土、澱粉、蔗糖、矽膠、滑石、矽藻土、尿素、碳酸鈣、碳酸鈉及重碳酸鈉及硫酸鈉。液體稀釋劑包括(例如)水、N,N－二甲基羧醯胺、二甲亞碸、N－烷基吡咯啶酮、乙二醇、聚丙二醇、石蠟、烷基苯、烷基萘、丙三醇、三乙酸甘油酯、橄欖油、蓖麻油、亞麻子油、桐油、芝麻油、玉米油、花生油、棉子油、大豆油、油菜粉油及椰子油、脂肪酸酯、諸如環己酮、2－庚酮、異佛爾酮及4－羥基－4－甲基－2－戊酮之酮、乙酸酯及諸如甲醇、環己醇、癸醇及四氫糠醇之醇。Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkyl phenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, benzenes Alkyl sulfonate, organopolyfluorene oxide, N,N-dialkyl taurate, sulfonic acid lignin, naphthalenesulfonic acid formaldehyde condensate, polycarboxylate, glyceride, polyoxyethylene/polyoxypropylene Dilute block copolymers and alkyl polyglycosides, the unit number of glucose (referred to as the degree of polymerization (DP)) may be in the range of 1 to 3 and the alkyl unit may be in the range of C 6 -C 1 4 (see Pure) And Applied Chemistry 72 , 1255-1264). Solid diluents include, for example, clays such as bentonite, microcrystalline kaolinite, attapulgite, and kaolin, starch, sucrose, silicone, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate, and sodium bicarbonate and sodium sulfate. Liquid diluents include, for example, water, N,N-dimethylcarboxamide, dimethyl hydrazine, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffin, alkylbenzene, alkylnaphthalene, Glycerol, triacetin, olive oil, castor oil, linseed oil, tung oil, sesame oil, corn oil, peanut oil, cottonseed oil, soybean oil, canola oil and coconut oil, fatty acid esters, such as cyclohexanone , 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone ketone, acetate and alcohols such as methanol, cyclohexanol, decyl alcohol and tetrahydrofurfuryl alcohol.

本發明之有用調配物亦可含有稱為調配物助劑之材料，其包括防沫劑、成膜劑及染料，且為熟習此項技術者所熟知。Useful formulations of the present invention may also contain materials known as formulation auxiliaries, including antifoaming agents, film formers, and dyes, and are well known to those skilled in the art.

防沫劑可包括含有諸如Rhodorsil416之聚有機矽氧烷之水分散性液體。成膜劑可包括聚乙酸乙烯酯、聚乙酸乙烯酯共聚物、聚乙烯吡咯啶酮－乙烯乙酸酯共聚物、聚乙烯醇、聚乙烯醇共聚物及蠟。染料可包括諸如Pro－lzed著色劑紅之水分散性液體染料組合物。熟習此項技術者應瞭解此為調配物助劑之非詳盡性清單。調配物助劑之合適實例包括本文中列出之調配物助劑與在McCutcheon之2001，第2卷：Functional Materials，由MC出版公司出版與PCT公開案WO 03/024222中列出之調配物助劑。Antifoaming agents may include such as Rhodorsil A water-dispersible liquid of 416 polyorganosiloxane. Film formers may include polyvinyl acetate, polyvinyl acetate copolymers, polyvinylpyrrolidone-ethylene acetate copolymers, polyvinyl alcohol, polyvinyl alcohol copolymers, and waxes. Dyes can include such as Pro-lzed Colorant Red Water Dispersible Liquid Dye Composition. Those skilled in the art should be aware that this is a non-exhaustive list of formulation auxiliaries. Suitable examples of formulation auxiliaries include the formulation auxiliaries listed herein and the formulations listed in McCutcheon 2001, Volume 2: Functional Materials, published by MC Publishing Company and PCT Publication WO 03/024222 Agent.

包括可乳濃縮物之溶液可藉由簡單混合該等成份來製備。粉劑與散劑可藉由摻合且通常在錘式粉碎機或水力粉碎機中碾磨來製備。懸浮液通常藉由濕磨法製備；參見(例如)U.S.3,060,084。顆粒與丸劑可藉由將活性材料噴霧至預成形之顆粒載劑或藉由結塊技術製備。參見Browning,"Agglomeration",Chemical Engineering ,1967年12月4日，第147－48頁，Perry's Chemical Engineer's Handbook ，第4版，McGraw－Hill，New York，1963，第8－57頁與其後頁及WO 91/13546。丸劑可藉由如U.S.4,172,714中之描述製備。水分散性或水溶性顆粒可藉由如U.S.4,144,050、U.S.3,920,442與DE 3,246,493中之教示製備。錠劑可藉由如U.S.5,180,587、U.S.5,232,701與U.S.5,208,030中之教示製備。薄膜可藉由如GB 2,095,558與U.S.3,299,566中之教示製備。A solution comprising a milk concentrate can be prepared by simply mixing the ingredients. Powders and powders can be prepared by blending and usually milling in a hammer mill or a hydraulic mill. Suspensions are usually prepared by wet milling; see, for example, US 3,060,084. Granules and pellets can be prepared by spraying the active material onto a preformed particulate carrier or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering , December 4, 1967, pp. 147-48, Perry's Chemical Engineer's Handbook , 4th Ed., McGraw-Hill, New York, 1963, pp. 8-57 and subsequent pages. WO 91/13546. Pellets can be prepared as described in U.S. Patent 4,172,714. The water-dispersible or water-soluble granules can be prepared by the teachings of U.S. Patent No. 4,144,050, U.S. Patent No. 3,920,442, the disclosure of which is incorporated herein. Lozenges can be prepared by the teachings of US 5,180,587, US 5,232,701 and US 5,208,030. Films can be prepared by the teachings of GB 2,095,558 and US 3,299,566.

關於調配物技術之另外資訊，參見T.Brooks及T.R.Roberts，編輯之Pesticide Chemistry and Bioscience,The Food－Environment Challenge ,Proceedings of the 9th International Congress on Pesticide Chemistry,The Royal Society of Chemistry,Cambridge,1999，第120－133頁中之T.S.Woods,"The Formulator's Toolbox－Product Forms for Modern Agriculture"。亦可參見U.S.3,235,361，第6行，第16列至第7行，第19列與實例10－41；U.S.3,309,192，第5行，第43列至第7行，第62列與實例8、12、15、39、41、52、53、58、132、138－140、162－164、166、167及169－182；U.S.2,891,855，第3行，第66列至第5行，第17列與實例1－4；Klingman，Weed Control as a Science ，John Wiley與Sons，Inc.，New York，1961，81－96頁；及Hance等人，Weed Control Handbook ，第8版，Blackwell Scientific Publications,Oxford,1989；及Developments in formulation technology，PJB Publications,Richmond,UK,2000。For additional information on formulation technology, see T. Brooks and TR Roberts, edited by Pesticide Chemistry and Bioscience, The Food-Environment Challenge , Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, 120th - TSWoods, "The Formulator's Toolbox-Product Forms for Modern Agriculture" on page 133. See also US 3,235,361, line 6, column 16 to line 7, column 19 and example 10-41; US 3,309,192, line 5, column 43 to line 7, column 62 and example 8 , 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167, and 169-182; US 2,891,855, line 3, column 66 to line 5, Columns 17 and 1-4; Klingman, Weed Control as a Science , John Wiley and Sons, Inc., New York, 1961, pages 81-96; and Hance et al, Weed Control Handbook , 8th edition, Blackwell Scientific Publications , Oxford, 1989; and Developments in formulation technology, PJB Publications, Richmond, UK, 2000.

在如下實例中，所有百分比按重量計且所有調配物以習知方法製備。化合物編號係指索引表A中之化合物。無需另外詳細描述，據信熟習此項技術者使用如上說明內容可最大程度應用本發明。因而如下實例僅為說明而建構，且不以任何方式限制於本揭示內容。除非另外說明，百分比按重量計。In the following examples, all percentages are by weight and all formulations are prepared in a conventional manner. The compound number refers to the compound in the index table A. Without further elaboration, it is believed that those skilled in the art will <RTIgt; The following examples are therefore merely illustrative and are not intended to be limiting in any way. The percentages are by weight unless otherwise stated.

實例A可濕性散劑 化合物1 65.0%十二烷基苯酚聚乙二醇醚 2.0%木質素磺酸鈉 4.0%矽鋁酸鈉 6.0%微晶高嶺石石(煅燒) 23.0% Example A Wettable Powder Compound 1 65.0% Dodecylphenol Polyglycol Ether 2.0% Sodium Lignosulfonate 4.0% Sodium Aluminate 6.0% Microcrystalline Kaolinite (Calcined) 23.0%

實例B顆粒Example B particle

實例C經擠壓丸劑 化合物5 25.0%無水硫酸鈉 10.0%粗木質素磺酸鈣 5.0%烷基萘磺酸鈉 1.0%鈣/鎂膨潤土 59.0% Example C Squeezed Pill Compound 5 25.0% anhydrous sodium sulfate 10.0% crude calcium lignosulfonate 5.0% sodium alkylnaphthalene sulfonate 1.0% calcium/magnesium bentonite 59.0%

實例D可乳化濃縮物 化合物9 20.0%油溶性磺酸酯及聚氧乙烯醚之摻合物 10.0%異佛爾酮 70.0% Example D emulsifiable concentrate Compound 9 20.0% blend of oil-soluble sulfonate and polyoxyethylene ether 10.0% isophorone 70.0%

實例E微乳液 化合物30 5.0%聚乙烯基吡咯啶酮－乙酸乙烯酯共聚物 30.0%烷基多醣苷 30.0%甘油單油酸酯 15.0%水 20.0% Example E Microemulsion Compound 30 5.0% polyvinylpyrrolidone-vinyl acetate copolymer 30.0% alkylpolyglycoside 30.0% glycerol monooleate 15.0% water 20.0%

實例F種子處理 化合物31 20.00%聚乙烯吡咯啶酮－乙酸乙烯酯共聚物 5.00%褐煤酸蠟 5.00%木質素磺酸鈣 1.00%聚氧乙烯/聚氧丙烯嵌段共聚物 1.00%硬脂醇(POE20) 2.00%聚有機矽烷 0.20%著色劑紅染料 0.05%水 65.75% Example F Seed Treatment Compound 31 20.00% polyvinylpyrrolidone-vinyl acetate copolymer 5.00% montanic acid wax 5.00% calcium lignosulfonate 1.00% polyoxyethylene/polyoxypropylene block copolymer 1.00% stearyl alcohol ( POE20) 2.00% polyorganodecane 0.20% colorant red dye 0.05% water 65.75%

實例G肥料棒Example G fertilizer rod

本發明之化合物藉由有利代謝及/或土壤殘留圖案來表徵且展示出控制一系列農藝與非農藝無脊椎害蟲之活性。本發明之化合物亦由展示移位作用以保護未直接與包含本發明化合物之無脊椎害蟲控制組合物接觸的葉及其他植物部分的植物中有利之葉及/或土壤施加系統性(soil－applied systemicity)來表徵。在本揭示內容之範圍內，"無脊椎害蟲控制"意謂抑制無脊椎害蟲之發展(包括死亡、進食減少及/或交配混亂)且導致無脊椎害蟲食用或傷害農作物或引起對建築結構的損壞顯著減少；相關表述類似定義。The compounds of the invention are characterized by advantageous metabolism and/or soil residual patterns and exhibit activity to control a range of agronomic and non-agronomic invertebrate pests. The compounds of the present invention are also systemically (soil-applied) by plants that exhibit a translocation action to protect leaves and other plant parts that are not directly in contact with the invertebrate pest control composition comprising the compound of the invention. Systemicity) to characterize. Within the scope of the present disclosure, "invertebrate pest control" means inhibiting the development of invertebrate pests (including death, reduced feeding and/or mating disorder) and causing invertebrate pests to eat or injure crops or cause damage to building structures. Significantly reduced; related expressions are similarly defined.

術語"農藝的"係指諸如用於食物及纖維之田間作物之生產且包括玉米、大豆及其他豆類、稻、穀(例如小麥、燕麥、大麥、黑麥、稻、玉米)、葉菜(例如萵苣、甘藍及其他油菜作物)、果菜(例如番茄、胡椒、茄子、十字花科植物及葫蘆)、馬鈴薯、甘薯、葡萄、棉花、樹果(例如梨果、核果及柑橘類)、小果(漿果、櫻桃)及其他特產作物(例如菜籽、向日葵及橄欖)之種植。術語"農藝的"亦係指含有由基因工程(例如轉基因)引入或藉由突變作用經修飾的遺傳物質以提供有利特性之該等作物的生產。該等特性之實例包括除草劑耐受性、對植食性害蟲(例如昆蟲、蟎、蚜蟲、蜘蛛、線蟲、蝸牛、植物致病性真菌、細菌及病毒)的抗性、改良的植物生長、對諸如高溫及低溫、低或高土壤水份及高鹽度之不利生長條件增加的耐受性、增加的開花或結果、更大的收穫產量、更快速的成熟、收穫產物更高的品質及/或營養價值及對所收穫產物改良的儲存或加工性質。轉基因植物可經修飾而表現多種特性。含有由基因工程或突變作用提供的特性之植物的實例包括諸如YIELD GARD、KNOCKOUT、STARLINK、BOLLGARD、NuCOTN及NEWLEAF之表現殺蟲蘇力菌(Bacillus thuringiensis )毒素之玉米、棉花、大豆及馬鈴薯變異體及諸如ROUNDUP READY、LIBERTY LINK、IMI、STS及CLEARFIELD之玉米、棉花、大豆及油菜籽的耐除草劑變異體，以及表現N－乙醯基轉移酶(GAT)以提供草甘膦除草劑抗性之作物，或含有HRA基因以提供對抑制乙醯乙酸酯合酶(ALS)之除草劑之抗性的作物。The term "agronomic" refers to the production of field crops such as for food and fiber and includes corn, soybeans and other legumes, rice, cereals (eg wheat, oats, barley, rye, rice, corn), leafy vegetables (eg Lettuce, kale and other canola crops), fruits and vegetables (eg tomato, pepper, eggplant, cruciferous and gourd), potatoes, sweet potatoes, grapes, cotton, tree fruits (eg pear fruit, stone fruit and citrus), small fruit (berry , cherry) and other specialty crops (such as rapeseed, sunflower and olive). The term "agronomic" also refers to the production of such crops containing genetic material that has been introduced by genetic engineering (eg, a transgene) or modified by mutation to provide advantageous properties. Examples of such properties include herbicide tolerance, resistance to herbivorous pests such as insects, mites, mites, spiders, nematodes, snails, phytopathogenic fungi, bacteria and viruses, improved plant growth, Increased tolerance to adverse growth conditions such as high and low temperatures, low or high soil moisture and high salinity, increased flowering or results, greater harvest yield, faster maturation, higher quality of harvested products and/or Or nutritional value and improved storage or processing properties of the harvested product. Transgenic plants can be modified to exhibit a variety of properties. Examples of plants containing properties provided by genetic engineering or mutation include, for example, YIELD GARD KNOCKOUT , STARLINK , BOLLGARD , NuCOTN And NEWLEAF Bacillus thuringiensis toxins of corn, cotton, soybean and potato variants and such as ROUNDUP READY , LIBERTY LINK IMI , STS And CLEARFIELD Herbicide-tolerant variants of corn, cotton, soybean and rapeseed, and crops that exhibit N-acetyltransferase (GAT) to provide glyphosate herbicide resistance, or contain HRA genes to provide inhibition of acetamidine A herbicide resistant crop of acetate synthase (ALS).

術語"非農藝的"係指其他園藝作物(例如非田間生長之溫室、苗圃或觀賞植物)、城市及工業環境中之住宅與商業結構、草坪(商業、高爾夫、住宅、娛樂等)、木材產品、儲存產品、農林及植被管理、公共衛生(人類)及動物衛生(家養動物、寵物、家畜、家禽、例如野生動物之非家養動物)應用。出於無脊椎害蟲控制範圍及經濟重要性之原因，藉由控制無脊椎害蟲來保護農作物不受由無脊椎動物引起的損害或傷害為本發明之實施例。The term "non-agronomic" refers to other horticultural crops (eg greenhouses, nurseries or ornamental plants that are not grown in the field), residential and commercial structures in urban and industrial environments, lawns (commercial, golf, residential, recreational, etc.), wood products. , storage products, agriculture, forestry and vegetation management, public health (human) and animal health (domestic animals, pets, livestock, poultry, non-domestic animals such as wild animals) applications. Protecting crops from damage or injury caused by invertebrates by controlling invertebrate pests is an embodiment of the invention for reasons of invertebrate pest control and economic importance.

如本揭示內容中所述，術語"無脊椎害蟲"包括經濟重要性害蟲中之節肢動物、腹足動物及線蟲。術語"節肢動物"包括昆蟲、蟎、蜘蛛、蠍子、蜈蚣、千足蟲、球潮蟲及結合綱。術語"腹足動物"包括蝸牛、蛞蝓及其他有柱腹足目動物(Stylommatophora)。術語"線蟲"包括所有蠕蟲，例如蛔蟲、犬惡絲蟲及植食性線蟲(Nematoda)、吸蟲(Tematoda)、棘頭綱(Acanthocephala)及絛蟲(Cestoda)。本發明之化合物展示出對抗範圍廣泛之食葉、食果、食莖或根、食籽、水棲及土棲性無脊椎害蟲之活性，該等害蟲為農作物、森林、溫室作物、觀賞植物、苗圃作物之生長及儲存、儲存食物及纖維產品、家畜、家庭、公共衛生及動物衛生的害蟲。熟習此項技術者將瞭解並非所有化合物具有對抗所有害蟲之所有生長階段的同等功效。As described in this disclosure, the term "invertebrate pest" includes arthropods, gastropods, and nematodes among economically important pests. The term "arthropod" includes insects, mites, spiders, scorpions, scorpions, millipedes, ball worms, and combinations. The term "gastropod" includes snails, snails and other Stylommatophora. The term "nematode" includes all helminths such as aphids, canines and Nematoda, Tematoda, Acanthocephala and Cestoda. The compounds of the present invention exhibit activity against a wide range of leaf, fruit, stem or root, foodseed, aquatic and soil invertebrate pests, such as crops, forests, greenhouse crops, ornamental plants, nurseries Crop growth and storage, storage of food and fiber products, livestock, household, public health and animal health pests. Those skilled in the art will appreciate that not all compounds have the same efficacy against all stages of growth of all pests.

農業或非農業害蟲包括鱗翅目之卵、幼蟲及成蟲，諸如夜蛾科中之黏蟲、夜盜蟲、尺蠖及heliothines(例如秋黏蟲(夜盜蟲(Spodoptera fugiperda J.E.Smith))、甜菜黏蟲(甜菜夜蛾(Spodoptera exigua Hbner)、黑夜盜蟲(球菜夜蛾(Agrotis ipsilon Hufnagel))、甘藍尺獲(擬尺蠖(Trichoplusia ni Hbner))、煙草食心蟲(煙芽夜蛾(Heliothis virescens Fabricius))；螟蛾科之蛀蟲、鞘蛾幼蟲、結網毛蟲、錐形蟲、卷葉菜蟲及雕葉蟲(例如歐洲玉米螟(歐洲玉米螟(Ostrinia nubilalis Hbner))、臍橙蟲(Amyelois transitella Walker)、玉米根結毛網蟲(Crambus caliginosellus Clemens)、諸如草地結毛網蟲(Herpetogramma licarsisalis Walker)之草地結毛網蟲(螟蛾：草螟科(Pyralidae：Crambinae )))；卷蛾科之卷葉蟲、食心蟲、種子蠕蟲及果實蠕蟲(例如小蘋果蛾(蘋果蠹蛾(Cydia pomonella Linnaeus))、葡萄漿果蛾(葡萄果實蛀蟲(Endopiza viteana Clemens))、東方果蛾(東方果實蛾(Grapholita molesta Busck)))；及多種其他經濟上重要之鱗翅(例如菱背蛾(小菜蛾(Plutella xylostella Linnaeus))、棉紅鈴蟲(棉紅鈴蟲(Pectinophora gossypiella Saunders))、舞毒蛾(舞毒蛾(Lymantria dispar Linnaeus)))；蜚蠊目之卵、若蟲與成蟲，包括姬蜚蠊科與蜚蠊科之蟑螂(例如東方蟑螂(東方蜚蠊(Blatta orientalis Linnaeus))、亞洲蟑螂(亞洲蟑螂(Blatella asahinai Mizukubo))、德國蟑螂(德國蜚蠊(Blattella germanica Linnaeus))、棕帶蟑螂(棕帶蜚蠊(Supella longipalpa Fabricius))、美洲蟑螂(美洲蜚蠊(Periplaneta americana Linnaeus))、棕色蟑螂(棕色蜚蠊(Periplaneta brunnea Burmeister))、馬得拉蟑螂(馬得拉蜚蠊(Leucophaea maderae Fabricius))、煙棕蟑螂(煙褐蜚蠊(Periplaneta fuliginosa Service))、澳大利亞蟑螂(澳洲蜚蠊(Periplaneta australasiae Fabr.))、龍蝦紅蟑螂(灰色蟑螂(Nauphoeta cinerea Olivier))及平滑蟑螂(Symploce pallens Stephens))；鞘翅目之卵、食葉、食果、食根、食籽及食泡沫組織之幼蟲與成蟲，包括長角象蟲科、豆象科及象蟲科之象鼻蟲(例如棉籽象鼻蟲(棉鈴象甲(Anthonomus grandis Boheman))、稻水象鼻蟲(水稻水象鼻蟲(Lissorhoptrus oryzophilus Kuschel))、穀象(穀象(Sitophilus granarius Linnaeus))、稻象(米象(Sitophilus oryzae Linnaeus))、一年生藍草象鼻蟲(Listronotus maculicollis Dietz)、藍草穀象(Sphenophorus parvulus Gyllenhal)、獵穀象(Sphenophorus venatus vestitus)、丹佛穀象(Sphenophorus cicatristriatus Fahraeus))；葉甲科之蚤甲蟲、黃瓜甲蟲、食蟲、葉甲蟲、馬鈴薯甲蟲及斑潛蠅(例如科羅拉多馬鈴薯甲蟲(馬鈴薯甲蟲(Leptinotarsa decemlineata Say))、西玉米食蟲(玉米根蟲(Diabrotica virgifera virgifera LeConte)))；Scaribaeidae科之金龜子與其他甲蟲(例如日本甲蟲(日本金龜子(Popillia japonica Newman))、東方甲蟲(Anomala orientalis Waterhouse)、北方面罩金龜子(Cyclocephala borealis Arrow)、南方面罩金龜子(Cyclocephala immaculata Olivier)、黑絨金龜(黑絨金龜(Ataenius spretulus Haldeman))、綠六月甲蟲(Cotinis nitida Linnaeus)、亞洲花園甲蟲(栗瑪絨金龜(Maladera castanea Arrow))、五月/六月甲蟲(金龜子(Phyllophaga spp.))、及歐洲金龜子(歐洲鰓金龜(Rhizotrogus majalis Razoumowsky)))；皮蠹科之地毯甲蟲；叩頭蟲科之鐵線蟲；長小蠹科之樹皮甲蟲及擬步行蟲科之麵粉甲蟲。另外，農藝與非農藝害蟲包括：革翅目之卵、成蟲與幼蟲，其包括球螋科之地蜈蚣(例如歐洲地蜈蚣(Forficula auricularia Linnaeus)、黑地蜈蚣(Chelisoches morio Fabricius))；半翅目與同翅目之卵、未成熟個體、成蟲與若蟲，諸如盲蝽科之植物臭蟲、蟬科之蟬、大葉蟬科之葉蟬(例如小綠葉蟬(Empoasca spp.))、Fulgoroidae科與飛虱科之飛虱、角蟬科之樹蚤、木虱科之木虱、粉虱科之粉虱科、蚜科之蚜蟲、葡萄根瘤蚜科之葡萄根瘤蚜、假介殼蟲科之粉蚧、介殼蟲科、珠綿蚧亞科、盾蚧科之介殼蟲、網蝽科之花編蟲、蝽象科之臭蝽、長蝽科之臭蟲(例如多毛臭蟲(Blissus leucopterus hirtus Montandon)與南方臭蟲(Blissus insularis Barber))與其他種子臭蟲、沫蟬科之沫蟬、緣蝽科之南瓜蟲及紅蝽科之紅蝽與棉蝽。亦包括蟎目(蟎)之卵、幼蟲、若蟲及成蟲，諸如葉蟎科之蛛蟎與紅蟎(例如歐洲紅蟎(歐洲葉蟎(Panonychus ulmi Koch))、二點蛛蟎(二點葉蟎(Tetranychus urticae Koch))、麥克丹尼爾蟎(邁葉蟎(Tetranychus mcdanieli McGregor)))；偽葉蟎科之扁平蟎(例如柑桔扁平蟎(葡萄紅蜘蛛(Brevipalpus lewisi McGregor)))；癭蟎科之鏽蟎與芽蟎及其他食葉蟎及在人類與動物衛生方面重要之蟎類，Epidermoptidae科之塵蟎、蠕形蟎科之毛囊蟲、食甜蟎科之穀蟎、蜱目之扁虱(例如鹿虱(胛硬蜱(Ixodes scapularis Say))、澳大利亞麻痺虱(全環硬蜱)Ixodes holocyclus Neumann))、美洲狗虱(變異革蜱(Dermacentor variabitis Say))、孤星虱(美洲花蜱(Amblyomma americanum Linnaeus)))及癢蟎科、蒲蟎科(Pyemotidae)及疥蟎科之痂蟎與疥蟎；直翅目之卵、成蟲與未成熟個體，其包括蚱蜢、蝗蟲及蟋蟀(例如遷徙蝗蟲(例如血黑蝗(Melanoplus sanguinipes Fabricius)、M.differentialis Thomas)、美洲蝗蟲(Schistocerca americana Drury)、沙漠蝗蟲(沙漠飛蝗(Schistocerca gregaria Forskal))、遷徙蝗蟲(飛蝗(Locusta migratoria Linnaeus))、灌木蝗蟲(Zonocerus spp.)、家蟋蟀(蟋蟀(Acheta domesticus Linnaeus))、蛄螻(例如茶色蛄螻(褐色蛄螻(Scapteriscus vicinus Scudder))與南方蛄螻(南方蛄螻(Scapteriscus borellii Giglio－Tos)))；雙翅目之卵、成蟲與未成熟個體，包括潛葉蛾、蚊類、果蠅(實蠅科)、釉蠅(例如瑞典稈蠅(Oscinella frit Linnaeus))、土壤食肉蠅、家蠅(例如家蠅(Musca domestica Linnaeus))、小家蠅(例如夏廁蠅(Fannia canicularis Linnaeus)、F.femoralis Stein)、螯蠅(例如廄螯蠅(Stomoxys calcitrans Linnaeus))、面蠅、角蠅、麗蠅(例如金蠅(Chrysomya spp.)、麗蠅(Phormia spp.))、及其他苔蘚蠅害蟲、馬蠅(例如馬蠅(Tabanus spp.))、斑點蠅(例如馬蠅屬(Gastrophilus spp.)、牛虻屬(Oestrus spp))、牛皮蠅(例如皮蠅屬(Hypoderma spp.))、鹿蠅(例如斑虻屬(Chrysops spp.))、羊蜱蠅(例如綿羊虱蠅(Melophagus ovinus Linnaeus))及其他短角亞目、蚊類(例如伊蚊屬(Aedes spp.)、瘧蚊屬(Anopheles spp.)、家蚊屬(Culex spp.))、黑蠅(例如原蚋屬(Prosimulium spp.)、蚋屬(Simulium spp.))、刺蚊、沙蠅、尖眼蕈蚊及其他長角亞目；纓翅目之卵、未成熟個體及成蟲，包括洋蔥薊馬(蔥薊馬(Thrips tabaci Lindeman))、花薊馬(花薊馬屬(Frankliniella spp.))及其他食葉薊馬；膜翅目之昆蟲害蟲包括螞蟻(例如紅匠蟻(Camponotus ferrugineus Fabricius)、黑匠蟻(木蟻(Camponotus pennsylvanicus De Geer))、法老蟻(小黃家蟻(Monomorium pharaonis Linnaeus))、小火蟻(火蟻(Wasmannia auropunctata Roger))、火蟻(Solenopsis geminata Fabricius)、入侵紅火蟻(入侵紅火蟻(Solenopsis invicta Buren))、阿根廷蟻(Iridomyrmex humilis Mayr)、瘋蟻(狂蟻(Paratrechina longicornis Latreille))、行道蟻(灰黑皺家蟻(Tetramorium caespitum Linnaeus))、玉米田蟻(Lasius alienus Frster)、臭家蟻(臭家蟻(Tapinoma sessile Say))、蜜蜂(包括木蜂)、大黃蜂、鮮黃色胡蜂、黃蜂及葉蜂(葉蜂屬(Neodiprion spp.)、莖蜂屬(Cephus spp.))；蟻科之昆蟲害蟲包括佛羅里達木匠蟻(木蟻(Camponotus floridanus Buckley))、白足蟻(Technomyrmex albipes fr.Smith)、大頭蟻(大頭家蟻屬(Pheidole sp.))及幽靈蟻(黑頭慌蟻(Tapinoma melanocephalum Fabricius))；等翅目之昆蟲害蟲包括白蟻科(例如大白蟻屬(Macrotermes sp.))、木白蟻科(例如堆砂白蟻屬(Cryptotermes sp.))及犀白蟻科(例如散白蟻屬(Reticulitermes sp.)、家白蟻屬(Coptotermes sp.))之白蟻、東部地下白蟻(黃肢散白蟻(Reticulitermes flavipes Kollar))、西部地下白蟻(Reticulitermes hesperus Banks)、臺灣地下白蟻(臺灣家白蟻(Coptotermes formosanus Shiraki))、西印度乾木白蟻(Incisitermes immigrans Snyder)、粉桿白蟻(Cryptotermes brevis Walker)、乾木白蟻(Incisitermes snyderi Light)、東南地下白蟻(Reticulitermes virginicus Banks)、西部乾木白蟻(小楹白蟻(Incisitermes minor Hagen))、諸如象白蟻屬之樹棲白蟻及其他經濟上重要之白蟻；諸如蠹魚(衣魚(Lepisma saccharina Linnaeus))與家衣魚(小灶衣魚(Thermobia domestica Packard))之纓尾目昆蟲害蟲；食毛目與包括攻擊人類及動物之頭蝨(頭蝨(Pediculus humanus capitis De Geer))、體虱(體虱(Pediculus humanus Linnaeus))、雞體虱(Menacanthus stramineus Nitszch)、狗刺虱(犬食毛虱(Trichodectes canis De Geer))、毛虱(Goniocotes gallinae De Geer)、綿羊體虱(Bovicola ovis Schrank)、短鼻牛虱(牛虱(Haematopinus eurysternus Nitzsch))、長鼻牛虱(Linognathus vituli Linnaeus)及其他嚼吸式寄生虱類之昆蟲害蟲；蚤目之昆蟲害蟲包括影響哺乳動物及鳥類之東方鼠蚤(印度鼠蚤(Xenopsylla cheopis Rothscbild))、貓蚤(貓蚤(Ctenocephalides felis Bouche))、狗蚤(狗蚤(Ctenocephalides canis Curtis))、雞蚤(Ceratophyllus gallinae Schrank)、黏貼蚤(雞貼蚤(Echidnophaga gallinacea Westwood))、人蚤(人蚤(Pulex irritans Linnaeus))及其他蚤類。另外覆蓋之節肢動物害蟲包括：蜘蛛目之蜘蛛，諸如棕色隱蜘蛛(褐絲蛛(Loxosceles reclusa Gertsch & Mulaik))與黑寡婦蜘蛛(黑寡婦蜘蛛(Latrodectus mactans Fabricius))及蚰蜓目之蜈蚣，諸如家蜈蚣(Scutigera coleoptrata Linnaeus)。本發明之化合物亦對線蟲綱、多節絛蟲綱、吸蟲綱及棘頭綱之成員有效，其成員包括圓線蟲目、蛔目、尖尾目、小桿目、旋尾目及刺嘴目經濟上重要之成員，諸如(但不限於)經濟上重要之農業害蟲(即根結線蟲屬(Meloidogyne )之根癌線蟲、根腐線蟲屬(Pratylenchus )之腐蝕線蟲、殘根線蟲屬(Trichodorus )之殘根線蟲等)與動物與人之衛生害蟲(即所有經濟上重要之吸蟲、絛蟲及蛔蟲，諸如馬之普通圓形線蟲(Strongylus vulgaris )、狗之犬蛔蟲(Toxocara canis )、綿羊之綿羊線蟲(Haemonchus contortus )、狗之犬心絲蟲(Dirofilaria immitis Leidy)、馬之葉狀裸頭絛蟲(Anoplocephala perfoliata )、反芻類之肝吸蟲(Fasciola hepatica Linnaeus)等)。Agricultural or non-agricultural pests include lepidopteran eggs, larvae and adults, such as the armyworm, night larvae, ticks and heliothines (eg, Spodoptera fugiperda JESmith), beet armyworm (Beetworm moth ( Spodoptera exigua H Bner), night worm ( Agrotis ipsilon Hufnagel), cabbage stalk ( Trichoplusia ni H Bner)), tobacco borer ( Heliothis virescens Fabricius); locust moth, sheath moth larvae, netted caterpillar, cone-shaped worm, leaf-leaf worm and leaf-cutting worm (eg European corn borer ( European Corn Borer ( Ostrinia nubilalis H Bner)), Amyelois transitella Walker, Crambus caliginosellus Clemens, Grasshopper worms such as Herpetogramma licarsisalis Walker (Pyralidae: Crambinae ) )); leaf curler, heartworm, seed worm, and fruit worm (such as Cydia pomonella Linnaeus), grape berry moth ( Endopiza viteana Clemens), Oriental fruit moth ( Grapholita molesta Busck); and a variety of other economically important lepidoptera (eg, Plutella xylostella Linnaeus), cotton bollworm ( Pectinophora gossypiella) Saunders)), Gypsy moth ( Lymantria dispar Linnaeus)); eggs of the eye, nymphs and adults, including the genus Aphididae and the genus Polygonaceae (eg Oriental 蟑螂 ( Batta orientalis Linnaeus) )), Asian 蟑螂 ( Blatella asahinai Mizukubo), German 蟑螂 ( Battella germanica Linnaeus), brown belt 棕 (Brown belt 蜚蠊 ( Supella l Ongipalpa Fabricius)), Periplaneta americana Linnaeus, Periplaneta brunnea Burmeister, Leucophaea maderae Fabricius, Burmese Periplaneta fuliginosa Service, Australian Periplaneta australasiae Fabr., Nauphoeta cinerea Olivier and Symploce pallens Stephens; Coleoptera Larvae and adult larvae of eggs, leaf, fruit, roots, seeds, and foams, including weevils of the genus Corydalis, the genus Bean, and the genus Iridae (such as cottonseed weevil (cotton) Anthonomus grandis Boheman, rice water weevil ( Lissorhoptrus oryzophilus Kuschel), valley elephant ( Sitophilus granarius Linnaeus), rice elephant ( Sitophilus oryzae Linnaeus) , annual blue weevil ( Listronotus maculicollis Dietz), Sphenophorus parvulus Gyllenhal, Sphenophorus venatus vestitus, Denver Valley Elephant ( S Phenophorus cicatristriatus Fahraeus)); locust beetle, cucumber beetle, insectivore, leaf beetle, potato beetle and zebrafish (such as the Colorado potato beetle ( Leptinotarsa decemlineata Say)), western corn worm (corn rootworm) Diabrotica virgifera virgifera LeConte))); scarab of Scaribaeidae family and other beetles (eg Japanese beetle ( Papiillia japonica Newman), Oriental beetle ( Anomala orientalis Waterhouse), Cyclocephala borealis Arrow, South side cover chafer ( Cyclocephala immaculata Olivier), Ataenius spretulus Haldeman, Cotinis nitida Linnaeus, Asian garden beetle ( Maadera castanea Arrow), May/June beetle ( Phyllophaga spp.) and the European chafer ( Rhozotrogus majalis Razoumowsky); the carpet beetle of the dermatology; the worm of the genus Trichomonas; the bark beetle and the genus Pseudomonas Flour beetle. In addition, agronomic and non-agronomic pests include: eggs of the genus Hydatid , adults and larvae, including mantles of the genus Corydalis (eg, Forficula auricularia Linnaeus, Chelisoches morio Fabricius); Eggs of the order Homoptera, immature individuals, adults and nymphs, such as plant bugs of the genus Aphididae, cockroaches of the genus Polygonaceae, leaf mites of the genus Euphorbiaceae (eg Empoasca spp.), Fulgoroidae虱 之 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱 虱, scale insects, subfamily of the genus Aphididae, the genus of the genus Shield, the flower worm of the genus Aphididae , the skunk of the genus Aphididae , and the bedbug of the genus Longiaceae (such as Blissus leucopterus hirtus Montandon) and the south Blissus insularis (Barber) and other seed bugs, the mites of the genus Moss , the pumpkin worms of the genus Polygonaceae, and the red mites and cotton aphids of the red carp family. Also included are eggs (larvae), larvae, nymphs, and adults, such as spider mites and red dragonflies (such as the European red pheasant ( Panonychus ulmi Koch), two-pointed spider mites (two-point leaf) Tetranychus urticae Koch), Tetranychus mcdanieli McGregor); flat warts of the genus Pseudostellariae ( eg Brevipalpus lewisi McGregor); Branches of rust and buds and other leafhoppers and important mites in human and animal health, the dust mites of the Epidermoptidae family, the hairy worms of the genus Demodex, the glutinous stalks of the family, the scorpion虱 (eg Ixodes scapularis Say), Australian cockroach ( Ixodes holocyclus Neumann), American cockroach ( Dermacentor variabitis Say), Lone Star 虱 (American Amblyomma americanum Linnaeus) and ticks, Pyemotidae and medlars; Orthoptera eggs, adult and immature individuals, including mites, mites and mites (eg migratory mites (eg Melanoplus sanguinipes Fabr Icius), M.differentialis Thomas), Schistocerca americana Drury, desert locust ( Schistocerca gregaria Forskal), migratory locust ( Locusta migratoria Linnaeus), shrub locust ( Zenocerus spp.), family carp ( Acheta domesticus Linnaeus), 蛄蝼 (eg, Scapteriscus vicinus Scudder and Scapteriscus borellii Giglio-Tos); eggs of the order Diptera, Adult and immature individuals, including leaf miners, mosquitoes, fruit flies (Tephritidae), glaze flies (eg Oscinella frit Linnaeus), soil carnivores, house flies (eg Musca domestica Linnaeus) )), Musca domestica (such as Fannia canicularis Linnaeus, F. femoralis Stein), larvae (such as Stomoxys calcitrans Linnaeus), face flies, horn flies, flies (such as gold flies ( Chrysomya spp.), Phormia spp., and other moss fly pests, horse flies (eg, Tabanus spp.), spotted flies (eg, Gastrophilus spp., Arctium ( Oestrus) Spp)), leather fly (eg Hypoderma spp.), deer flies (eg Chrysops spp.), sheep flies (eg Melophagus ovinus Linnaeus) and other short-horned suborders, mosquitoes ( For example, Aedes spp., Anopheles spp., Culex spp., black flies (eg Prosimulium spp., Simulium spp.) , Anopheles mosquitoes, sand flies, sharp-eyed mosquitoes and other longhorned suborders; eggs of the order Thyme, immature individuals and adults, including onion thrips ( Thrips tabaci Lindeman), flower thrips (flowers) Frankliniella spp.) and other leaf-eating thrips; insects of the Hymenoptera include ants (eg Camponotus ferrugineus Fabricius, Camponotus pennsylvanicus De Geer), Pharaoh Ants ( monomorium pharaonis Linnaeus), small fire ants ( Wasmannia auropunctata Roger), fire ants ( Solenopsis geminata Fabricius), invasive red fire ants ( Solenopsis invicta Buren), Argentine ants (Iridomyrmex humilis Mayr), crazy ant (crazy ant (Paratrechina longicornis Latreille)) Way street ant (dark gray wrinkle house ant (Tetramorium caespitum Linnaeus)), cornfield ant (Lasius alienus F Rster ), snail ( Tapiinoma sessile Say), bees (including wood bees), bumblebee, fresh yellow wasps, wasps and leaf bees (Lepidoptera ( Neodiprion spp.), Stem ( Sphingus) Spp.)); insect pests of the family Antaceae include Florida carpenter ants ( Camponotus floridanus Buckley), white ants ( Technomyrmex albipes fr. Smith), big-headed ants ( Pheidole sp.) and ghosts Ant ( Talinoma melanocephalum Fabricius); Isoptera insect pests include termites (eg Macrotermes sp.), wood termites (eg Cryptotermes sp.) and rhinoceros Termites (eg, termites of Reticulitermes sp., Coptotermes sp.), eastern termites ( Reticulitermes flavipes Kollar), western termites ( Reticulitermes hesperus Banks), Taiwan subterranean termites (Taiwan termite (Coptotermes formosanus Shiraki)), the West Indian dry wood termites (Incisitermes immigrans Snyder), powder rod termites (Cryptotermes brevis Walker), dry wood termites (Incisitermes snyderi Light), East Subterranean termite (Reticulitermes virginicus Banks), western dry wood termites (termite small Ying (Incisitermes minor Hagen)), such as the importance of the arboreal termite termite termite genus and other economic; such as silverfish (Silverfish (Lepisma saccharina Linnaeus) ) and the insect-infested pest of the family fish ( Thermobia domestica Packard); the genus of the genus and the head mites ( Pediculus humanus capitis De Geer), body lice (body 虱) ( Pediculus humanus Linnaeus)), Menacanthus stramineus Nitszch, Dog Hedgehog ( Trichodectes canis De Geer), Goniocotes gallinae De Geer, Bovicola ovis Schrank, Short nose Burdock ( Haematopinus eurysternus Nitzsch), Linognathus vituli Linnaeus and other insect pests of the chewing parasitic mites ; the insect pests of the order include the oriental squirrel affecting mammals and birds (India) rat flea (Xenopsylla cheopis Rothscbild)), cat flea (cat flea (Ctenocephalides felis Bouche)), dog flea (dog flea (Ctenocephalides canis Curtis)), chicken (Ceratophyllus gallinae Schrank), adhesive flea (flea chicken paste (Echidnophaga gallinacea Westwood)), human flea (human flea (Pulex irritans Linnaeus)) and other fleas. Also covered arthropod pests include: spiders of the spider eye, such as the brown hidden spider ( Loxosceles reclusa Gertsch & Mulaik) and the black widow spider ( Latrodectus mactans Fabricius) and the eye of the eye, Such as the family ( Scutigera coleoptrata Linnaeus). The compounds of the present invention are also effective against members of the nematode, the polychaete, the trematode, and the scorpion, and the members thereof include the genus A. elegans, the genus Aphididae, the scutellaria, the snail, the snail, and the spurs. Important members such as, but not limited to, economically important agricultural pests (ie, root worms of the genus Meloidogyne , rot nematodes of the genus Pratylenchus , and genus of the genus Trichodorus ) Root-worm, etc.) and animal-to-human hygiene pests (ie all economically important flukes, mites and mites, such as the strong worm ( Strongylus vulgaris ), the dog toad mites ( Toxocara canis ), the sheep nematode ( Haemonchus contortus ), Dirofilaria immitis Leidy, Anoplocephala perfoliata , Fasciola hepatica Linnaeus, etc.

本發明之化合物尤其顯示出針對下列害蟲之高活性，鱗翅目中之害蟲(例如Alabama argillacea Hbner(棉葉波紋葉蛾)、Archips argyrospila Walker(果樹黃卷蛾)、A.rosana Linnaeus(歐洲卷葉蛾(European leaf roller))及其他蛾(Archips )種，Chilo suppressalis Walker(二化螟)、Cnaphalocrosis medinalis Guenee(稻縱卷葉螟)、Crambus caliginosellus Clemens(玉米根草螟)、Crambus teterrellus Zincken(早熟禾草螟)、Cydia pomonella Linnaeus(蘋果蠹蛾)、Earias insulana Boisduval(埃及金剛鑽)、Earias vittella Fabricius(斑點螟蛉(spotted bollworm))、Helicoverpa armigera Hbner(番茄夜蛾)、Helicoverpa zea Boddie(歐洲玉米穗蟲)、Heliothis virescens Fabricius(美洲煙葉蛾)、Herpetogramma licarsisalis Walker(草地螟蟲(sod webworm))、Lobesia botrana Denis & Schiffermller(葡萄漿果小卷蛾)、Pectinophora gossypiella Saunders(紅鈴蟲)、Phyllocnistis citrella Stainton(橘細潛蛾)、Pieris brassicae Linnaeus(大菜粉蛾)、Pieris rapae Linnaeus(小菜粉蝶)、Plutella xylostella Linnaeus(小菜蛾)、Spodoptera exigua Hbner(甜菜夜蛾)、Spodoptera litura Fabricius(斜紋夜蛾、烏秋蟲)、Spodoptera frugiperda J.E.Smith(草地黏蟲)、Trichoplusia ni Hbner(粉紋夜蛾)及Tuta absoluta Meyrick(西紅柿潛夜蛾))。The compounds of the invention in particular exhibit high activity against the following pests, pests of the order Lepidoptera (eg Alabama argillacea H bner (cotton leaf corrugated leaf miners), Archips argyrospila Walker (yellow fruit moth), A.rosana Linnaeus (European leaf roller (European leaf roller)) and other moth (Archips) species, Chilo suppressalis Walker (rice stem borer) , Cnaphalocrosis medinalis Guenee (rice leaf roller), Crambus caliginosellus Clemens (corn borer blades of grass), Crambus teterrellus Zincken (bluegrass webworm), Cydia pomonella Linnaeus (codling moth), Earias insulana Boisduval (Egypt diamond), Earias Vittella Fabricius (spotted bollworm), Helicoverpa armigera H Bner ( T. californica), Helicoverpa zea Boddie (European corn ear worm), Heliothis virescens Fabricius (American tobacco leaf moth), Herpetogramma licarsisalis Walker (sod webworm), Lobesia botrana Denis & Schifferm Ller ( P. berry), Pectinophora gossypiella Saunders, Phyllocnistis citrella Stainton, Pieris brassicae Linnaeus, Pieris rapae Linnaeus, Plutella xylostella Linnaeus Moth), Spodoptera exigua H Bner (Beet armyworm), Spodoptera litura Fabricius (Striata, Uygur), Spodoptera frugiperda JESmith (Grassworm), Trichoplusia ni H Bner ( Turnosum ) and Tuta absoluta Meyrick (Tomato).

本發明之化合物亦對下害蟲具有顯著之活性，同翅目之成員，包括：Acyrthisiphon pisum Harris(豌豆蚜)、Aphis craccivora Koch(豆蚜)、Aphis fabae Scopoli(蠶豆蚜)、Aphis gossypii Glover(棉蚜、瓜蚜)、Aphis pomi De Geer(蘋果蚜)、Aphis spiraecola Patch(繡線菊蚜)、Aulacorthum solani Kaltenbach(馬鈴薯長須蚜)、Chaetosiphon fragaefolii Cockerell(草莓毛管蚜)、Diuraphis noxia Kurdjumov/Mordvilko(俄羅斯麥雙尾蚜)、Dysaphis plantaginea Paaserini(蘋粉紅劣蚜)、Eriosoma lanigerum Hausmann(蘋果棉蚜)、Hyalopterus pruni Geoffroy(梅大尾蚜)、Lipaphis erysimi Kaltenbach(偽菜蚜)、Metopolophium dirrhodum Walker(穀蚜)、Macrosipum euphorbiae Thomas(茄長管蚜)、Myzus persicae Sulzer(桃蚜、青苔)、Nasonovia ribisnigri Mosley(萵苣蚜)、Pemphigus spp.(根蚜屬及癭棉蚜屬)、Rhopalosiphum maidis Fitch(玉米縊管蚜)、Rhopalosiphum padi Linnaeus(粟縊管蚜)、Schizaphis graminum Rondani(麥二叉蚜)、Sitobion avenae Fabricius(麥長管蚜)、Therioaphis maculata Buckton(苜蓿彩斑蚜)、Toxoptera aurantii Boyer de Fonscolombe(橘二岔蚜)、及Toxoptera citricida Kirkaldy(大桔蚜)，Adelges spp.(球蚜屬)，Phylloxera devastatrix Pergande(美核桃根瘤蚜)，Bemisia tabaci Gennadius(煙草粉虱、棉粉虱)、Bemisia argentifolii Bellows & Perring(銀葉粉虱)、Dialeurodes citri Ashmead(柑桔粉虱)及Trialeurodes vaporariorum Westwood(溫室白粉虱)，Empoasca fabae Harris(蠶豆微葉蟬)、Laodelphax striatellus Fallen(斑飛虱)、Macrolestes quadrilineatus Forbes(紫莞葉蟬)、Nephotettix cinticeps Uhler(大青葉蟬)、Nephotettix nigropictus Stl(黑尾葉蟬)、Nilaparvata lugens Stl(褐稻虱)、Peregrinus maidis Ashmead(玉米飛虱)、Sogatella furcifera Horvath(白背飛虱)、Sogatodes orizicola Muir(美洲稻飛蝨)、Typhlocyba pomaria McAtee蘋白小葉蟬、Erythroneoura spp.(斑葉蟬屬)，Magicidada septendecim Linnaeus(週期蟬)，Icerya purchasi Maskell(吹綿介殼蟲)、Quadraspidiotus perniciosus Comstock(梨圓盾蚧)，Planococcus citri Risso(柑桔粉介殼蟲)，Pseudococcus spp.(其他粉蚧複合體)，Cacopsylla pyricola Foerster(木虱)、Trioza diospyri Ashmead(柿木虱)。The compounds of the invention also have significant activity against lower pests, members of the order Homoptera, including: Acyrthisiphon pisum Harris (pea peas), Aphis craccivora Koch (bean meal ), Aphis fabae Scopoli (broad bean mites), Aphis gossypii Glover (cotton) Aphis pomi De Geer, Aphis spiraecola Patch, Aulacorthum solani Kaltenbach, Chaetosiphon fragaefolii Cockerell, Diuraphis noxia Kurdjumov/Mordvilko (Russia) Wheat double-tailed owl), Dysaphis plantaginea Paaserini, Eriosoma lanigerum Hausmann, Hyalopterus pruni Geoffroy, Lipaphis erysimi Kaltenbach, Metopolophium dirrhodum Walker ), Macrosipum euphorbiae Thomas, Myzus persicae Sulzer, peach, moss, Nasonovia ribisnigri Mosley, Pemphigus spp., Rhopalosiphum maidis Fitch Piper ), Rhopalosiphum padi Linnaeus, Millaphis graminum Rondan i ( Mc bifurcation), Sitobion avenae Fabricius, Therioaphis maculata Buckton, Toxoptera aurantii Boyer de Fonscolombe, and Toxoptera citricida Kirkaldy Adelges spp., Phylloxera devastatrix Pergande, Bemisia tabaci Gennadius, Tomisia argentifolii Bellows & Perring, Dialeurodes citri Ashmead Whitefly) and Trialeurodes vaporariorum Westwood (Greenhouse Whitefly), Empoasca fabae Harris (Lepidoptera), Laodelphax striatellus Fallen, Macrolestes quadrilineatus Forbes, Nephotettix cinticeps Uhler , Nephotettix nigropictus St l (black-tailed spider owl ), Nilaparvata lugens St l (Brown Rice), Peregrinus maidis Ashmead, Sogatella furcifera Horvath, Sogatodes orizicola Muir, Typhlocyba pomaria McAtee, Erythroneoura spp. Id ), Magicidada septendecim Linnaeus (cycle 蝉 ), Icerya purchasi Maskell (Blowing Scale ), Quadraspidiotus perniciosus Comstock (Pear Shield), Planococcus citri Risso ( Purple Powder Scale ), Pseudococcus spp. Complex), Cacopsylla pyricola Foerster, Trioza diospyri Ashmead.

本發明之化合物亦具有針對下列害蟲之活性，半翅目中之成員，包括：Acrosternum hilare Say(喜綠蝽)、Anasa tristis De Geer(番瓜綠椿)、Blissus leucopterus leucopterus Say(多毛長蝽)、Corythuca gossypii Fabricius(棉帶蝽(cotton lace bug))、Cyrtopeltis modesta Distant(西紅柿蝽(tomato bug))、Dysdercus suturellus Herrich－Schffer(棉蝽象)、Euchistus servus Say(褐臭蝽)、Euchistus variolarius Palisot de Beauvois(一點蝽象(one－spotted stink bug))、Graptosthetus spp.(種蝽之複合體)、Leptoglossus corculus Say(葉足松種蝽(leaf－footed pine seed bug))、Lygus lineolaris Palisot de Beauvois(牧草盲蝽)、Nezara viridula Linnaeus(稻綠蝽)、Oebalus pugnax Fabricius(美洲稻盾蝽)、Oncopeltus fasciatus Dallas(大馬利筋蝽(large milkweed bug))、Pseudatomoscelis seriatus Reuter(棉盲蝽(cotton fleahopper))。其他本發明之化合物可控制之昆蟲目包括纓翅目(例如Frankliniella occidentalis Pergande(苜蓿薊馬)、Scirthothrips citri Moulton(柑橘薊馬(citrus thrip))、Sericothrips variabilis Beach(大豆薊馬(soybean thrip))、及Thrips tabaci Lindeman(煙薊馬))，及鞘翅目(例如Leptinotarsa decemlineata Say(馬鈴薯甲蟲)、Epilachna varivestis Mulsant(墨西哥豆瓢蟲)及叩甲屬(Agriotes )、Athous 屬或金針蟲屬(Limonius )之金針蟲)。The compounds of the present invention also have activity against the following pests, members of the Hemiptera, including: Acrosternum hilare Say, Anasa tristis De Geer, Blissus leucopterus leucopterus Say (polychaete) , Corythuca gossypii Fabricius (cotton lace bug), Cyrtopeltis modesta Distant (tomato bug), Dysdercus suturellus Herrich-Sch Wer (cotton), Euchistus servus Say, Euchistus variolarius Palisot de Beauvois (one-spotted stink bug), Graptosthetus spp. ( Leptoglossus corculus Say) Leaf -footed pine seed bug, Lygus lineolaris Palisot de Beauvois, Nezara viridula Linnaeus, Oebalus pugnax Fabricius, Oncopeltus fasciatus Dallas (Malaysia) Large milkweed bug), Pseudatomoscelis seriatus Reuter (cotton fleahopper). Other insect control species of the present invention include Thysanoptera (e.g. Frankliniella occidentalis Pergande, Scirthothrips citri Moulton (citrus thrip), Sericothrips variabilis Beach (soybean thrip) And Thrips tabaci Lindeman, and Coleoptera (eg Leptinotarsa decemlineata Say), Epilachna varivestis Mulsant, and Agriotes , Athous or Golden Needles ( Limonius) ) Golden Needle).

應注意本發明之化合物用於控制銀葉粉虱之用途。應注意本發明之化合物用於控制蠶豆微葉蟬之用途。應注意本發明之化合物用於控制玉米飛虱之用途。應注意本發明之化合物用於控制棉蚜之用途。應注意本發明之化合物用於控制桃蚜之用途。應注意本發明之化合物用於控制小菜蛾之用途。應注意本發明之化合物用於控制草地黏蟲之用途。It should be noted that the compounds of the invention are useful for controlling silver leaf whitefly. It should be noted that the compounds of the present invention are useful for controlling the broadleaf of broad bean. It should be noted that the compounds of the invention are useful for controlling corn planthoppers. It should be noted that the compounds of the invention are useful for controlling cotton aphid. It should be noted that the compounds of the invention are useful for controlling peach aphid. It should be noted that the compounds of the invention are useful for controlling Plutella xylostella. Attention should be paid to the use of the compounds of the invention for controlling grass worms.

本發明之化合物亦可與一或多種其他生物活性化合物或藥劑混合，其包括殺蟲劑、殺真菌劑、殺線蟲劑、殺菌劑、殺蟎劑、除草劑，諸如根促進劑、化學滅菌劑、化學信息素、拒避劑、引誘劑、外激素、進食促進劑之生長調節劑，其他生物活性化合物或昆蟲致病細菌、病毒或真菌，從而形成多組份殺蟲劑以提供更廣泛範圍之農藝或非農藝用途。因此本發明亦係關於一種包含生物有效量的式1 化合物及有效量的至少一種額外生物活性化合物或藥劑且可另外包含至少一種界面活性劑、固體稀釋劑或液體稀釋劑之組合物。其他生物活性化合物或藥劑可以包含至少一種界面活性劑、固體或液體稀釋劑之組合物來調配。對於本發明之混合物而言，其他生物活性化合物或藥劑可與包括式1 化合物之本發明化合物一起調配以形成預混合物，或其他生物活性化合物或藥劑可與包括式1 化合物之本發明化合物分別進行調配，且在施用前(例如在噴霧槽中)將兩種調配物組合在一起或者相繼施用。The compounds of the invention may also be combined with one or more other biologically active compounds or agents, including insecticides, fungicides, nematicides, bactericides, acaricides, herbicides, such as root promoters, chemical sterilants , chemical pheromones, repellents, attractants, pheromones, growth regulators for food-promoting agents, other biologically active compounds or insect-borne bacteria, viruses or fungi to form multi-component pesticides to provide a wider range Agronomic or non-agricultural use. The invention is therefore also directed to a composition comprising a biologically effective amount of a compound of formula 1 and an effective amount of at least one additional biologically active compound or agent and which may additionally comprise at least one surfactant, solid diluent or liquid diluent. Other biologically active compounds or agents may be formulated with a combination of at least one surfactant, solid or liquid diluent. For the mixtures of the invention, other biologically active compounds or agents may be formulated with a compound of the invention comprising a compound of formula 1 to form a premix, or other biologically active compound or agent may be separately reacted with a compound of the invention comprising a compound of formula 1 Formulation, and the two formulations are combined together or sequentially prior to administration (eg, in a spray tank).

可與本發明之化合物調配之該等生物活性化合物或藥劑的實例為：殺蟲劑，例如阿巴汀(abamectin)、歐殺松(acephate)、亞滅培(acetamiprid)、胺氟滅(amidoflumet，S－1955)、阿維菌素(avermectin)、印苦楝子素(azadirachtin)、穀硫磷(azinphos－methyl)、畢芬寧(bifenthrin)、畢芬載(bifenazate)、布芬淨(buprofezin)、加保扶(carbofuran)、培丹(cartap)、克芬那比(chlorfenapyr)、克福隆(chlorfluazuron)、陶斯松(chlorpyrifos)、甲基陶斯松(chlorpyrifos－methyl)、環蟲醯肼(chromafenozide)、可尼丁(clothianidin)、西福托芬(cyflumetofen)、賽扶寧(cyfluthrin)、β－賽扶寧、賽洛寧(cyhalothrin)、λ－賽洛寧、賽滅寧(cypermethrin)、賽滅淨(cyromazine)、第滅寧(deltamethrin)、戴芬西隆(diafenthiuron)、二嗪農(diazinon)、地特靈(dieldrin)、二福隆(diflubenzuron)、四氟甲醚菊酯(dimefluthrin)、樂果(dimethoate)、呋蟲胺(dinotefuran)、戴芬蘭(diofenolan)、伊曼美丁(emamectin)、安殺番(endosulfan)、益化利(esfenvalerate)、伊希普(ethiprole)、苯硫威(fenothiocarb)、芬諾西克(fenoxycarb)、芬普寧(fenpropathrin)、芬化利(fenvalerate)、費普尼(fipronil)、氟啶蟲醯胺(flonicamid)、氟苯二醯胺(flubendiamide)、護賽寧(flucythrinate)、福化利(tau－fluvalinate)、氟魯芬(flufenerim，UR－50701)、氟芬隆(flufenoxuron)、氟諾斯(fonophos)、鹵芬載(halofenozide)、六伏隆(hexaflumuron)、伏蟻腙(hydramethylnon)、益達胺、茚蟲威(indoxacarb)、亞芬松(isofenphos)、祿芬隆(lufenuron)、馬拉硫磷(malathion)、麥特氟米腙(metaflumizone)、聚乙醛(metaldehyde)、甲胺磷(methamidophos)、殺撲磷(methidathion)、滅多蟲(methomyl)、美賜年(methoprene)、甲氧氯(methoxychlor)、甲氧苄氟菊酯(metofluthrin)、久效磷(monocrotophos)、甲氧芬載(methoxyfenozide)、烯啶蟲胺(nitenpyram)、尼賽新(nithiazine)、諾華隆(novaluron)、諾氟隆(noviflumuron，XDE－007)、歐殺滅(oxamyl)、對硫磷(parathion)、甲基對硫磷(parathion－methyl)、百滅寧(permethrin)、甲拌磷(phorate)、伏殺磷(phosalone)、亞胺硫磷(phosmet)、磷胺(phosphamidon)、抗蚜威(pirimicarb)、丙溴磷(profenofos)、丙氟菊酯(profluthrin)、吡蚜酮(pymetrozine)、派福若(pyrafluprole)、除蟲菊素(pyrethrin)、啶蟲丙醚(pyridalyl)、吡普若(pyriprole)、比普西芬(pyriproxyfen)、魚藤酮(rotenone)、蘭尼定(ryanodine)、賜諾殺(spinosad)、螺二克芬(spirodiclofen)、螺甲蟎酯(spiromesifen，BSN 2060)、螺泰曲美(spifotetramat)、硫丙磷(sulprofos)、得布芬載(tebufenozide)、得福隆(teflubenzuron)、七氟菊酯(tefluthrin)、託福松(terbufos)、殺蟲畏(tetrachlorvinphos)、噻蟲啉(thiacloprid)、噻蟲嗪、硫雙威(thiodicarb)、硫殺太鈉(thiosultap－sodium)、泰滅寧(tralomethrin)、唑蚜威(triazamate)、三氯磷酸酯(trichlorfon)及殺蟲隆(triflumuron)；殺真菌劑，例如酸化苯幷噻二唑(acibenzolar)、吲唑磺菌胺(amisulbrom)、亞托敏(azoxystrobin)、免賴得(benomyl)、殺稻瘟菌素－S(blasticidin)、波爾多(Bordeaux)混合物(硫酸三銅)、博克利(boscalid)、溴克座(bromuconazole)、加普胺(carpropamid)、四氯丹(captafol)、蓋普丹(captan)、貝芬替(carbendazim)、地茂散(chloroneb)、四氯異苯腈(chlorothalonil)、氯氧化銅、銅鹽、噻芬胺(cyflufenamid)、霜脲氰(cymoxanil)、環克座(cyproconazole)、賽普洛(cyprodinil)、(S)－3,5－二氯－N －(3－氯－1－乙基－1－甲基－2－氧丙基)－4－甲基苯甲醯胺(RH 7281)、二氯西莫(S－2900)、噠菌清、氯硝胺、苯醚甲環唑、(S)－3,5－二氫－5－甲基－2－(甲硫基)－5－苯基－3－(苯基胺基)－4H－咪唑－4－酮(RP 407213)、達滅芬、二甲氧菌胺(dimoxystrobin)、達克利、M－達克利、多寧、護粒松、氟環唑、噁唑菌酮、咪唑菌酮、芬瑞莫、芬克座、芬克咪(fencaramid)(SZX0722)、拌種咯、苯鏽啶、粉鏽啉、三苯醋錫、三苯氫氧化錫(fentin hydroxide)、扶吉胺、護汰寧、氟美醯胺(RPA 403397)、氟莫呋/氟莫啉(flumorf/flumorlin)(SYP－L190)、氟氧菌胺(HEC 5725)、氟啶醯菌胺(fluopicolide)氟喹唑(fluquinconazole)、護矽得(flusilazole)、氟多寧(flutolanil)、護汰芬(flutriafol)、福爾培(folpet)、乙磷鋁(fosetyl－aluminum)、呋霜靈(furalaxyl)、福安他吡(furametapyr，S－82658)、己唑醇(hexaconazole)、依普克唑(ipconazole)、丙基喜樂松(iprobenfos)、依普酮(iprodione)、亞賜圃(isoprothiolane)、春日黴素(kasugamycin)、克收欣(kresoxim－methyl)、錳粉克(mancozeb)、雙炔醯菌胺(mandipropamid)、錳乃浦(maneb)、高效甲霜靈(mefenoxam)、滅鏽胺(mepronil)、滅達樂(metalaxyl)、葉菌唑(metconazole)、苯氧菌胺/芬敏特羅賓(metominostrobin/fenominostrobin，SSF－126)、米特拉芬諾(metrafenone，AC375839)、邁克尼(myclobutanil)、甲胂鐵銨(neoasozin，鐵甲胂酸銨)、尼克吡芬(nicobifen，BAS 510)、奧瑞菌胺(orysastrobin)、歐殺斯(oxadixyl)、平克座(penconazol)、賓克隆(pencycuron)、噻菌靈(probenazole)、吡噻菌胺(penthiopyrad)、咪醯胺(prochloraz)、霜黴威(propamocarb)、普克利(propiconazole)、普羅喹那(proquinazid，DPX－KQ926)、丙硫醇克唑(prothioconazole，JAU 6476)、比芬諾(pyrifenox)、百克敏(pyraclostrobin)、派美尼(pyrimethanil)、百快隆(pyroquilon)、快諾芬(quinoxyfen)、司比羅胺(spiroxamine)、硫磺、得克利(tebuconazole)、氟醚唑(tetraconazole)、噻苯咪唑(thiabendazole)、塞氟滅(thifluzamide)、甲基多保淨(thiophanate－methyl)、得恩地(thiram)、汰敵寧(tiadinil)、三泰芬(triadimefon)、三泰隆(triadimenol)、三賽唑(tricyclazoles)、三氟敏(trifloxystrobin)、環菌唑(triticonazol)、維利微素(validamycin)及免克寧(vinclozolin)；殺線蟲劑，例如得滅克(aldicarb)、歐殺滅(oxamyl)及芬滅松(fenamiphos)；殺菌劑，例如鏈黴素(streptomycin)；殺蟎劑，例如三亞蟎(amitraz)、滅蟎猛(chinomethionat)、殺蟎酯(chlorobenzilate)、環己錫(cyhexatin)、開樂散(dicofol)、得氯蟎(dienochlor)、伊妥咢坐(etoxazole)、芬那劄奎(fenazaquin)、芬布賜(fenbutatin oxide)、芬普寧、芬普蟎(fenpyroximate)、合賽多(hexythiazox)、克蟎特(propargite)、噠蟎靈(pyridaben)及吡蟎胺(tebufenpyrad)；及生物藥劑，包括昆蟲致病細菌，例如蘇力菌亞莎華(aizawai )亞種、蘇力菌卻氏卡奇(kurstaki )亞種及蘇力菌封囊δ內毒素(例如，Cellcap、MPV、MPVII)；昆蟲致病真菌，例如綠僵病真菌(green muscardine fungus)；及昆蟲致病病毒，包括桿狀病毒、諸如HzNPV、AfNPV之核多角體病毒(NPV)；及諸如CpGV之顆粒病毒。Examples of such biologically active compounds or agents which may be formulated with the compounds of the invention are: insecticides such as abamectin, acephate, acetamiprid, amidoflumet , S-1955), avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate, buprofezin, Carbofuran, cartap, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, Clothianidin, cyflumetofen, cyfluthrin, β-saiconing, cyhalothrin, λ-cylonin, cypermethrin, 赛灭净(cyromazine), deltamethrin, diafenthiuron, diazinon, dieldrin, diflubenzuron, dimefluthrin, Dimethoate, dinotefuran, diofenolan, iman beauty (emamectin), endosulfan, esfenvalerate, ethiprole, fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate ), fipronil, flonicamid, flubendiamide, flucythrinate, tau-fluvalinate, flufenerim, UR -50701), flufenoxuron, fonophos, hafenofozide, hexaflumuron, hydramethylnon, idadamine, indoxacarb, Isofenphos, lufenuron, malathion, metaflumizone, metaldehyde, methamidophos, methidathion ), methodom, metopor, methoxychlor, metofluthrin, monocrotophos, methoxyfenozide, acetamiprid Amine (nitenpyram), nithiazine, novaluron, novolonuron (XDE-007), Oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, imipenem (phosmet), phosphamidon, pirimicarb, profenofos, profluthrin, pymetrozine, pyrafluprole, pyrethrin (pyrethrin), pyridalyl, pyriprol, pyriproxyfen, rotenone, ryanodine, spinosad, spirulina (spirodiclofen), spiromesifen (BSN 2060), spifotetramat, sulprofos, tebufenozide, teflubenzuron, tefluthrin ( Tefluthrin), terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin , triazamate, trichlorfon and triflumuron; fungicides such as acidified benzothiazole (a Cibenzolar), amisulbrom, azoxystrobin, benomyl, blasticidin, Bordeaux mixture (tripper copper sulfate), bokley (boscalid), bromuconazole, carpropamid, captafol, captan, carbendazim, chloroneb, tetrachloroisobenzene Nitrothalonil, copper oxychloride, copper salt, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, (S)-3,5-dichloro - N- (3-Chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide (RH 7281), dichlorocarb (S-2900), sputum Clear, chloramine, difenoconazole, (S)-3,5-dihydro-5-methyl-2-(methylthio)-5-phenyl-3-(phenylamino)- 4H-imidazol-4-one (RP 407213), damethacin, dimoxystrobin, Dakli, M-Dakli, Donin, Pleurotus, epoxiconazole, famoxadone, imidazole Ketone, fenrexone, fenkelic, fencaramid (SZX0722), seed dressing Benzodiazepine, powder rust, triphenylacetate, fentin hydroxide, chlordiazepide, chloramphenicol, flumethalin (RPA 403397), flumofur/flumorf (flumorf/ Flumorlin) (SYP-L190), fluoxetamine (HEC 5725), fluopicolide fluquinconazole, flusilazole, flutolanil, defoliation Flutriafol), folfet, fosetyl-aluminum, furalaxyl, furametapyr (S-82658), hexaconazole, ipconazole ), iprobenfos, iprodione, isoprothiolane, kasugamycin, kresoxim-methyl, mancozeb, diacetylene Mandipropamid, manebole, mefenoxam, mepronil, metalaxyl, metconazole, phenoxybenzamine/phentermine Robin (metominostrobin/fenominostrobin, SSF-126), metrafenone (AC375839), myclobutanil, neoamozin, iron armor Ammonium), niclofen (BAS 510), oresastrobin, oxadixyl, penconazol, pencycuron, probenazole, pyrithione Penthiopyrad, prochloraz, propamocarb, propiconazole, proquinazid (DPX-KQ926), prothioconazole (JAU 6476), ratio Pyrifenox, pyraclostrobin, pyrimethanil, pyroquilon, quinoxyfen, spiroxamine, sulphur, tebuconazole, fluoroether Tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, triadimefon, Triadimenol, tricyclazoles, trifloxystrobin, triticonazol, validamycin, and vinclozolin; nematicides, such as dexamethasone (aldicarb), oxamyl and fenamiphos; fungicides, Such as streptomycin; acaricides, such as amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, chloranil (dienochlor), etoxazole, fenazaquin, fenbutatin oxide, fenprozin, fenpyroximate, hexythiazox, propargite ), pyridaben and tebufenpyrad; and biological agents, including insect-borne bacteria, such as the subspecies of Aizawai, Suricus , and kurstaki And S. cerevisiae δ endotoxin (eg, Cellcap, MPV, MPVII); insect pathogenic fungi, such as green muscardine fungus; and insect pathogenic viruses, including baculovirus, such as HzNPV, Nuclear polyhedrosis virus (NPV) of AfNPV; and particulate virus such as CpGV.

本發明之化合物及其組合物可施用於經基因轉型而表現對無脊椎害蟲具有毒性之蛋白質(例如蘇力菌δ內毒素)的植物。外部施用的本發明之無脊椎害蟲控制化合物之效應可與所表現之毒素蛋白形成增效。The compounds of the present invention and compositions thereof can be administered to plants which have been genetically engineered to exhibit a protein which is toxic to invertebrate pests, such as S. faecalis delta endotoxin. The effect of the externally administered invertebrate pest control compound of the present invention can be synergistic with the expressed toxin protein.

此等農業保護劑(意即殺蟲劑、殺真菌劑、殺線蟲劑、殺蟎劑、除草劑及生物藥劑)之一般參考文獻包括：The Pesticide Manual，第13版， C.D.S.Tomlin，編輯，British Crop Protection Council,Farnham,Surrey,U.K.,2003及The BioPesticide Manual，第2版， L.G.Copping，編輯，British Crop Protection Council,Farnham,Surrey,U.K.,2001。General references for such agricultural protective agents (ie, insecticides, fungicides, nematicides, acaricides, herbicides, and biologics) include: The Pesticide Manual, 13th Edition, CDSTomlin, ed., British Crop Protection Council, Farnham, Surrey, UK, 2003 and The BioPesticide Manual, 2nd edition, LGCopping, ed., British Crop Protection Council, Farnham, Surrey, UK, 2001.

在某些實例中，與具有類似控制範圍但作用模式不同之其他殺節肢動物劑的組合對於抗性管理而言將為尤其有利的。因此，本發明之組合物可另外包含生物有效量的至少一種額外的具有類似控制範圍但作用模式不同之無脊椎害蟲控制化合物或藥劑。使經基因修飾而表現植物保護性化合物(例如蛋白質)之植物或該植物之地點與生物有效量的本發明之化合物接觸亦可提供較寬範圍的植物保護且對於抗性管理而言係有利的。In certain instances, combinations with other arthropodicides having similar control ranges but different modes of action would be particularly advantageous for resistance management. Thus, the compositions of the present invention may additionally comprise a biologically effective amount of at least one additional invertebrate pest control compound or agent having a similar control range but different modes of action. Contacting a plant genetically modified to exhibit a plant protective compound (eg, a protein) or the location of the plant with a biologically effective amount of a compound of the invention may also provide a wide range of plant protection and is advantageous for resistance management. .

在某些實例中，本發明之化合物與其他無脊椎害蟲控制化合物或藥劑的組合可產生大於相加(意即增效)之效果及/或小於相加之效果(意即拮抗)。總是需要減少釋放於環境中的化學藥劑的量同時確保有效的害蟲控制。當於提供農藝學滿意程度的害蟲控制之施用率下出現無脊椎害蟲控制藥劑之增效作用時，該等組合可有利地用於降低作物生產成本且降低環境負擔。In certain instances, combinations of the compounds of the invention with other invertebrate pest control compounds or agents can produce greater than additive (i.e., synergistic) effects and/or less than additive effects (i.e., antagonistic). There is always a need to reduce the amount of chemicals released into the environment while ensuring effective pest control. When synergistic effects of invertebrate pest control agents occur at an application rate of pest control that provides agronomic satisfaction, such combinations can be advantageously used to reduce crop production costs and reduce environmental burden.

表A列出式1 化合物與其他無脊椎害蟲控制藥劑之特定組合以說明本發明之混合物、組合物及方法。表A之第一行列出特定無脊椎害蟲控制藥劑(例如第一列的"阿巴汀")。表A之第二行列出該無脊椎害蟲控制藥劑之作用模式(若已知)。表A之第三行列出該無脊椎害蟲控制藥劑相對於式1 化合物、其N －氧化物或鹽之施用率之重量比範圍的實施例(例如以重量計，阿巴汀相對於式1 化合物為"50：1至1：50")。因此，舉例而言，表A之第一列特定揭示可以介於50：1至1：50之間的重量比施用的式1 化合物與阿巴汀之組合。表A之其餘列應類似進行理解。另外應注意表A列出式1 化合物與其他無脊椎害蟲控制藥劑之特定組合以說明本發明之混合物、組合物及方法且包括施用率之重量比範圍的額外實施例，其中一些特定混合物顯示出值得關注的增效作用。Table A lists specific combinations of the compounds of Formula 1 with other invertebrate pest control agents to illustrate the mixtures, compositions, and methods of the present invention. The first row of Table A lists specific invertebrate pest control agents (eg, the first column of "Abartin"). The second row of Table A lists the mode of action (if known) of the invertebrate pest control agent. The third row of Table A lists examples of the weight ratio range of the application rate of the invertebrate pest control agent relative to the compound of formula 1 , its N -oxide or salt (for example, by weight, abatatin relative to the compound of formula 1 ) It is "50:1 to 1:50"). Thus, for example, the first column of Table A specifically discloses a combination of a compound of Formula 1 and abatatin that can be applied in a weight ratio between 50:1 and 1:50. The remaining columns of Table A should be similarly understood. Additionally, it should be noted that Table A lists additional combinations of compounds of Formula 1 with other invertebrate pest control agents to illustrate the mixtures, compositions, and methods of the present invention and that include a range of weight ratios of application rates, with some specific mixtures showing A synergy that deserves attention.

用於與本發明之化合物混合之殺蟲劑及殺蟎劑之一實施例包括：鈉通道調節劑類，例如賽滅寧、賽洛寧、賽扶寧、β－賽扶寧、益化利、芬化利、茚蟲威及泰滅寧；膽鹼酯酶抑制劑，例如滅多蟲、歐殺滅及硫雙威；新煙鹼類似物，例如亞滅培、可尼丁、益達胺、噻蟲啉及噻蟲嗪；神經元鈉通道阻斷劑類，例如茚蟲威；殺蟲大環內酯類，例如賜諾殺、阿巴汀、阿維菌素及伊曼美丁；GABA(γ－胺基丁酸)調節之氯通道阻斷劑，例如安殺番、伊希普及費普尼；幾丁質合成抑制劑類，例如氟芬隆及殺蟲隆；保幼激素模擬物，例如戴芬蘭及比普西芬；章魚胺受體配位體類，例如三亞蟎；蛻皮激素促效劑類，例如甲氧芬載及得布芬載；蘭尼定受體配位體類，例如蘭尼定、鄰胺苯甲醯胺及氟苯二醯胺；苯硫威；氟啶蟲醯胺；麥特氟米腙；啶蟲丙醚；及吡蚜酮。用於與本發明之化合物混合之生物藥劑之一實施例包括蘇力菌及蘇力菌δ內毒素以及天然存在及經基因修飾之病毒殺蟲劑，包括桿狀病毒科的成員以及昆蟲致病真菌。Examples of insecticides and acaricides for use in combination with the compounds of the present invention include: sodium channel modulating agents such as cyprodin, saronin, savonon, beta-syrene, and yihuali , Fenhua Li, Indoxacarb and Tetrin; cholinesterase inhibitors, such as chlorpyrifos, chlorpyrifos and thiodicarb; neonicotinoid analogues such as arsenic, cotinine, edamine , thiacloprid and thiamethoxam; neuronal sodium channel blockers, such as indoxacarb; insecticidal macrolides, such as spinosad, abatatin, avermectin and immanmetine; GABA (gamma-aminobutyric acid)-regulated chloride channel blockers, such as amphibians, Ishi universal Fipney; chitin synthesis inhibitors, such as flufensulfonate and insecticide; juvenile hormone simulation Such as Daifon and bepivoxil; octopamine receptor ligands, such as triterpenoids; ecdysone agonists, such as methoxyfen and debufen; lanidine receptors Classes such as lanidine, o-amine benzylamine and fluorobenzamide; phenylthiocarb; fluramide; metefluzamide; acetamiprid; and pymetrozine. Examples of biological agents for use in combination with a compound of the invention include Suribacter and S. faecalis delta endotoxin and naturally occurring and genetically modified viral insecticides, including members of the baculoviridae and insect pathogenicity Fungus.

包括式1 化合物、其N －氧化物或鹽之化合物與額外無脊椎害蟲控制藥劑之重量比通常為介於1000：1與1：1000之間，其中一實施例為介於500：1與1：500之間，另一實施例為介於250：1與1：200之間且另一實施例為介於100：1與1：50之間。The weight ratio of the compound comprising the compound of Formula 1 , its N -oxide or salt to the additional invertebrate pest control agent is typically between 1000:1 and 1:1000, wherein one embodiment is between 500:1 and 1 Between 500, another embodiment is between 250:1 and 1:200 and another embodiment is between 100:1 and 1:50.

下表B中列出包含本發明之混合物及/或式1 化合物(化合物編號係指索引表A中之化合物)及額外無脊椎害蟲控制藥劑之特定組合物的實施例。Examples of specific compositions comprising a mixture of the invention and/or a compound of formula 1 (compound number refers to a compound in index table A) and an additional invertebrate pest control agent are listed in Table B below.

表B中列出之特定混合物通常將式1 之化合物及/或索引表A中列出之化合物與其他無脊椎害蟲藥劑以表A中指出的比率組合。The particular mixtures listed in Table B typically combine the compounds of Formula 1 and/or the compounds listed in Index Table A with other invertebrate pest agents at the ratios indicated in Table A.

在農藝與非農藝應用中如下控制無脊椎害蟲：將生物有效劑量的包含本發明之化合物的組合物施用至害蟲之環境(包括受侵染之農藝及/或非農藝地點)、至待保護之區域或直接施用至待控制之害蟲上。農藝應用包括一般藉由將本發明之組合物或混合物施用至農作物種子(種植之前)、至農作物植物之葉、莖、花及/或果實，或在農作物種植之前或之後施用至土壤或其他生長介質以保護田間作物不受無脊椎害蟲侵害。非農藝應用係指非農作物種植田地之區域中的無脊椎害蟲控制。非農藝應用包括在儲存之穀物、豆類及其他糧食中，及在諸如衣服與地毯之紡織品中控制無脊椎害蟲。非農藝應用亦包括在觀賞性植物、森林、院落、道路沿線及鐵路沿線中，及在諸如草坪、高爾夫球道及牧場上控制無脊椎害蟲。非農藝應用亦包括在房屋中及其他可由人類及/或同伴佔用之建築物中、農場、大牧場、動物園或其他動物中控制害蟲。非農藝應用亦包括控制諸如白蟻之可損害木材或其他建築中所用結構材料之害蟲。Controlling invertebrate pests in agronomic and non-agronomic applications by applying a biologically effective amount of a composition comprising a compound of the invention to a pest environment (including infested agronomic and/or non-agronomic sites) to be protected The area is applied directly to the pest to be controlled. Agronomic applications include application to soil or other growth generally by applying the composition or mixture of the invention to crop seeds (before planting), to the leaves, stems, flowers and/or fruits of crop plants, or before or after crop planting Medium to protect field crops from invertebrate pests. Non-agronomic applications refer to invertebrate pest control in areas where non-agricultural crops are grown. Non-agronomic applications include controlling invertebrate pests in stored grains, beans and other foodstuffs, and in textiles such as clothing and carpets. Non-agronomic applications also include ornamental plants, forests, yards, along roads and along railways, and invertebrate pests such as lawns, golf courses and pastures. Non-agronomic applications also include controlling pests in houses and other buildings that can be occupied by humans and/or peers, farms, ranch, zoos or other animals. Non-agronomic applications also include controlling pests such as termites that can damage structural materials used in wood or other buildings.

非農藝應用亦包括藉由控制寄生性或傳染感染性疾病的無脊椎害蟲保護人類及動物健康。控制動物寄生蟲包括控制寄生於宿主動物體表(例如肩部、腋窩、腹部、腿內部)之外部寄生蟲及寄生於宿主動物體內(例如胃、腸、肺、血管、皮下、淋巴組織)之內部寄生蟲。外部寄生或傳染疾病的害蟲包括(例如)恙蟎、壁虱、虱、蚊子、蠅、疥、蟎及跳蚤。內部寄生蟲包括犬惡絲蟲、鉤蟲及蠕蟲。本發明之化合物及組合物尤其適於對抗外部寄生性或傳染疾病的害蟲。Non-agronomic applications also include the protection of human and animal health by invertebrate pests that control parasitic or infectious infectious diseases. Controlling animal parasites includes controlling external parasites that are parasitic on the surface of the host animal (eg, shoulders, armpits, abdomen, legs) and parasitic in host animals (eg, stomach, intestine, lung, blood vessels, subcutaneous, lymphoid tissue). Internal parasite. Pests of external parasitic or infectious diseases include, for example, ticks, ticks, ticks, mosquitoes, flies, ticks, ticks and fleas. Internal parasites include Dirofilaria, hookworms and helminths. The compounds and compositions of the present invention are particularly suitable for combating pests of external parasitic or infectious diseases.

本發明之化合物及組合物適於對抗侵擾以下動物之寄生蟲：農業勞動動物，諸如牛、綿羊、山羊、馬、豬、驢、駱駝、水牛、兔、母雞、火雞、鴨、鵝及蜂；寵物及家養動物，諸如狗、貓、寵物鳥類及觀賞魚；以及所謂的實驗動物，諸如倉鼠、豚鼠、大鼠及小鼠。藉由對抗此等寄生蟲，(在肉、奶/毛、絲、蛋、蜜等方面)死亡率及效能降低將減少，因此施用包含本發明之化合物的組合物使得可更經濟且更簡單地飼養動物。The compounds and compositions of the present invention are suitable for combating parasites that infest the following animals: agricultural labor animals such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, hens, turkeys, ducks, geese and Bees; pets and domestic animals such as dogs, cats, pet birds and ornamental fish; and so-called experimental animals such as hamsters, guinea pigs, rats and mice. By combating these parasites, the mortality and potency reduction (in terms of meat, milk/hair, silk, eggs, honey, etc.) will be reduced, so applying a composition comprising a compound of the invention makes it more economical and simpler Raise animals.

獸醫行業中之非農藝應用以已知方式進行，藉由以(例如)錠劑、膠囊、飲劑、浸潤製劑、顆粒、糊劑、boli、經由飼料程序、栓劑之形式經腸投藥；藉由諸如注射(包括肌肉內、皮下、靜脈內、腹膜內)、植入之非經腸投藥；藉由經鼻投藥；藉由以(例如)浸入或浸漬、噴霧、灌注、洗滌、以散劑塗覆及經由包含本發明之化合物或組合物之諸如頸圈、耳印、尾印、量肢卷尺(limb measuring tape)或韁繩之有形裝置的形式經皮投藥。Non-agronomic applications in the veterinary industry are carried out in a known manner by intestine administration in the form of, for example, tablets, capsules, concentrates, infiltrates, granules, pastes, boli, via a feed procedure, suppositories; Such as injection (including intramuscular, subcutaneous, intravenous, intraperitoneal), parenteral administration by implantation; by nasal administration; by, for example, immersion or dipping, spraying, infusing, washing, spraying with a powder And transdermal administration via the form of a tangible device comprising a compound or composition of the invention such as a collar, ear print, tail print, limb measuring tape or reins.

因此，本發明另外包含一種用於在農藝學及/或非農藝學應用中控制無脊椎害蟲之方法，其包含使該無脊椎害蟲或其環境與生物有效量的一或多種本發明之化合物或與包含至少一種該化合物之組合物或包含至少一種該化合物及生物有效量的至少一種額外生物活性化合物或藥劑之組合物接觸。包含本發明之組合物及生物有效量的至少一種額外生物活性化合物或藥劑之適當組合物之實例包括其中額外活性組合物與本發明之化合物存在於相同顆粒上或與本發明之化合物存在於獨立顆粒上之顆粒組合物。Accordingly, the present invention further comprises a method for controlling an invertebrate pest in an agronomic and/or non-agronomic application comprising the invertebrate pest or an environmentally and biologically effective amount thereof, one or more compounds of the invention or Contact with a composition comprising at least one such compound or a composition comprising at least one such compound and a biologically effective amount of at least one additional biologically active compound or agent. Examples of suitable compositions comprising a composition of the invention and a biologically effective amount of at least one additional biologically active compound or agent include wherein the additional active composition is present on the same particle as the compound of the invention or is present in isolation from the compound of the invention a particulate composition on the granules.

接觸方法之一實施例係藉由噴霧。或者可將包含本發明之化合物之顆粒組合物施用至植物葉或土壤。本發明之化合物亦可藉由使植物與包含本發明之化合物之組合物接觸經植物吸收來有效輸送，該組合物以土壤浸潤液之液體調配物、用於土壤之顆粒調配物、育苗盒處理或移植浸漬之形式來施用。應注意土壤浸潤液體調配物形式之本發明之組合物。亦應注意一種用於控制無脊椎害蟲之方法，其包含使生物有效劑量的本發明之化合物與無脊椎害蟲之土壤環境接觸。另外應注意本發明之化合物經由局部施用至感染位點亦有效。另一種接觸方法包括藉由直接及殘留噴霧、航空噴霧、凝膠、種子塗佈、微封囊、系統吸收、誘餌、耳簽、團塊、噴霧器、熏劑、氣溶膠、粉劑及數種其他方法施用本發明之化合物。接觸方法之一實施例為包含本發明之混合物或組合物之空間穩定性肥料顆粒、桿或錠劑。本發明之化合物亦可注入用於製造無脊椎動物控制裝置(例如昆蟲網)之材料中。種子塗佈可適用於所有類型的種子，包括經基因轉型而表現特性之植物由其萌發之種子。代表性實例包括其表現對無脊椎害蟲有毒性之蛋白質(諸如蘇力菌毒素)之植物種子或其表現除草劑抗性(諸如"抗農達"種子)之植物種子。One embodiment of the contacting method is by spraying. Alternatively, the particulate composition comprising the compound of the invention can be applied to plant leaves or soil. The compound of the present invention can also be efficiently delivered by contacting a plant with a composition comprising the compound of the present invention by a plant absorption, the composition being treated with a liquid formulation of a soil infiltration solution, a granular preparation for soil, and a seedling box treatment. Or in the form of a transplant impregnation. Attention should be paid to compositions of the invention in the form of soil infiltrated liquid formulations. Attention should also be directed to a method for controlling an invertebrate pest comprising contacting a biologically effective amount of a compound of the invention with a soil environment of an invertebrate pest. It should also be noted that the compounds of the invention are also effective by topical administration to the site of infection. Another method of contact includes direct and residual spray, aerial spray, gel, seed coating, microencapsulation, system absorption, bait, ear tags, pellets, sprays, fumigants, aerosols, powders and several others. Methods The compounds of the invention are administered. One embodiment of the contacting method is a sterically stabilized fertilizer granule, rod or lozenge comprising a mixture or composition of the invention. The compounds of the invention may also be infused into materials for the manufacture of invertebrate control devices, such as insect nets. Seed coating can be applied to all types of seeds, including seeds from which plants that have been genetically engineered to characterize their germination. Representative examples include plant seeds which exhibit proteins which are toxic to invertebrate pests, such as sulphotoxin, or plant seeds which exhibit herbicide resistance, such as "anti-Ronda" seeds.

可將本發明之化合物併入誘餌組合物，其由無脊椎害蟲進食或用於諸如誘捕器、毒餌站及其類似物之裝置中。該誘餌組合物可為顆粒之形式，其包含(a)活性成份，意即生物有效量的式1之化合物、其N－氧化物或鹽；(b)一或多種食物材料；視情況之(c)引誘劑；及視情況之(d)一或多種保濕劑。應注意包含約0.001－5%之間之活性成份，約40－99%之食物材料及/或引誘劑及視情況之約0.05－10%之保濕劑的顆粒或誘餌組合物，其以非常低之施用率，尤其在藉由攝取而非直接接觸致死之活性成份劑量下有效於控制土壤無脊椎害蟲。一些食物材料可同時起到食物來源與引誘劑之功能。食物材料包括碳水化合物、蛋白質及脂類。食物材料之實例為蔬菜粉、蔗糖、澱粉、動物脂肪、植物油、酵母萃取物及乳固體。引誘劑之實例為添味劑與食用香料，諸如水果或植物萃取物、香料、或其他動物或植物組份、信息素或其他已知引誘目標無脊椎害蟲之試劑。保濕劑(即濕度保持劑)之實例為乙二醇及其他多羥基化合物、甘油及山梨糖醇。應注意用於控制至少一種選自由螞蟻類、白蟻類及蟑螂類組成之群之無脊椎害蟲的誘餌組合物(及使用該誘餌組合物之方法)。一種用於控制無脊椎害蟲之裝置可包含誘餌組合物與適合容納誘餌組合物之外殼，其中該外殼具有至少一開口，其尺寸允許無脊椎害蟲穿過該開口從而無脊椎害蟲可自外殼外之位置得以接近誘餌組合物，且其中該外殼另外適合置放於或靠近潛在或已知的無脊椎害蟲活躍地點。The compounds of the invention may be incorporated into a bait composition that is eaten by invertebrate pests or used in devices such as traps, bait stations, and the like. The bait composition may be in the form of granules comprising (a) an active ingredient, meaning a biologically effective amount of a compound of formula 1, an N-oxide or a salt thereof; (b) one or more food materials; as the case may be ( c) an attractant; and optionally (d) one or more humectants. It should be noted that the granule or bait composition comprising between about 0.001% to about 5% of the active ingredient, from about 40% to about 99% of the food material and/or the attractant and, optionally, from about 0.05% to about 10% of the humectant, is very low The rate of application, especially at doses of the active ingredient that is lethal by ingestion rather than direct contact, is effective in controlling soil invertebrate pests. Some food materials can function as both a food source and an attractant. Food materials include carbohydrates, proteins and lipids. Examples of food materials are vegetable powder, sucrose, starch, animal fat, vegetable oil, yeast extract and milk solids. Examples of attractants are odorants and flavorants, such as fruit or plant extracts, flavors, or other animal or plant components, pheromones or other agents known to attract target invertebrate pests. Examples of humectants (i.e., moisture retaining agents) are ethylene glycol and other polyhydroxy compounds, glycerin and sorbitol. Attention should be paid to a bait composition (and a method of using the same) for controlling at least one invertebrate pest selected from the group consisting of ants, termites and mites. A device for controlling an invertebrate pest can comprise a bait composition and an outer casing adapted to receive a bait composition, wherein the outer casing has at least one opening sized to allow an invertebrate pest to pass through the opening such that the invertebrate pest can be external to the outer shell The location is accessible to the bait composition, and wherein the outer shell is additionally adapted to be placed at or near an active or known active location of the invertebrate pest.

本發明之化合物可無需其他佐劑而施用，但最常見之施用方法為調配物，其包含一或多種活性成份與合適的載劑、稀釋劑及界面活性劑且可能視最終用途與食物組合。一種施用方法涉及噴霧本發明之化合物之水分散液或精製油溶液。與噴霧油、噴霧油濃縮物、黏展劑、佐劑、其他溶劑及增效劑(諸如胡椒基丁醚)組合通常增強化合物之功效。在非農藝用途中，該等噴霧可自諸如罐、瓶或其他容器之噴霧容器，藉助泵或藉由密閉式容器(例如密閉式氣溶膠噴霧罐)將其釋放來施用。該等噴霧組合物可具有多種形式，例如噴霧、薄霧、泡沫、煙氣或霧。因此該等噴霧組合物視情況可進一步包含推進劑、發泡劑等。應注意包含生物有效量的本發明之化合物或組合物及載劑的噴霧組合物。該噴霧組合物之一實施例包含生物有效量的本發明之化合物或組合物及推進劑。代表性推進劑包括(但不限於)甲烷、乙烷、丙烷、丁烷、異丁烷、丁烯、戊烷、異戊烷、新戊烷、戊烯、氫氟碳化物、氯氟碳化物、二甲醚及前述之混合物。應注意用於控制至少一種選自由蚊子、黑蠅、螯蠅、鹿蠅、馬蠅、黃蜂、胡蜂、大黃蜂、壁虱、蜘蛛、螞蟻、蠓蟲及其類似動物組成之群之無脊椎害蟲(包括單獨或組合)的噴霧組合物(及使用自噴霧容器中分配之該噴霧組合物之方法)。The compounds of the present invention can be administered without the need for additional adjuvants, but the most common method of administration is a formulation comprising one or more active ingredients in association with suitable carriers, diluents and surfactants, and possibly in combination with the end use and food. One method of application involves spraying an aqueous dispersion or refined oil solution of a compound of the invention. Combinations with spray oils, spray oil concentrates, binders, adjuvants, other solvents, and synergists such as piperonyl butoxide typically enhance the efficacy of the compound. In non-agronomic applications, such sprays can be applied from a spray container such as a can, bottle or other container by means of a pump or by means of a closed container such as a closed aerosol spray can. The spray compositions can take a variety of forms such as sprays, mists, foams, fumes or mists. Accordingly, such spray compositions may further comprise a propellant, a blowing agent, and the like, as appropriate. Attention should be directed to a spray composition comprising a biologically effective amount of a compound or composition of the invention and a carrier. An embodiment of the spray composition comprises a biologically effective amount of a compound or composition of the invention and a propellant. Representative propellants include, but are not limited to, methane, ethane, propane, butane, isobutane, butene, pentane, isopentane, neopentane, pentene, hydrofluorocarbons, chlorofluorocarbons , dimethyl ether and mixtures of the foregoing. Attention should be paid to controlling at least one invertebrate pest selected from the group consisting of mosquitoes, black flies, larvae, deer flies, horse flies, wasps, wasps, bumblebees, ticks, spiders, ants, locusts and the like. (including singly or in combination) spray compositions (and methods of using the spray compositions dispensed from a spray container).

有效控制(意即"生物有效劑量")所需之施用率將視如待控制之無脊椎動物之種類、害蟲之生命週期、生命階段、其尺寸、地點、一年中之時間、宿主作物或動物、進食行為、交配行為、環境濕度、溫度及其類似因素而定。在正常情形下，每公頃約0.01至2 kg活性成份之施用率足夠控制農藝生態系統中之害蟲，但少至0.0001 kg/公頃亦可足夠或多至8 kg/公頃亦可能需要。對於農藝應用，有效使用率在約1.0至50 mg/平方米之範圍但少至0.1 mg/平方公尺亦可足夠或多至150 mg/平方公尺亦可能需要。熟習此項技術者可容易確定用於所要無脊椎害蟲控制水平需要之生物有效劑量。The rate of application required for effective control (ie "biologically effective dose") will depend on the species of invertebrate to be controlled, the life cycle of the pest, the life stage, its size, location, time of year, host crop or Animals, eating behavior, mating behavior, environmental humidity, temperature, and the like. Under normal conditions, an application rate of about 0.01 to 2 kg of active ingredient per hectare is sufficient to control pests in the agronomic ecosystem, but as little as 0.0001 kg/ha may be sufficient or as much as 8 kg/ha. For agronomic applications, effective use rates in the range of about 1.0 to 50 mg/m2 but as little as 0.1 mg/m2 may be sufficient or as much as 150 mg/m2. Those skilled in the art can readily determine the biologically effective dose required for the level of control of the desired invertebrate pest.

將增效作用描述為"混合物中兩種組份之協作效應，從而總體效應比兩種(或更多)單獨使用之效應之總和更大或更加延長"(參見P.M.L.Tames,Neth.J.Plant Pathology 1964,70,73－80)。兩種活性成份之間之增效效應之存在藉助Colby方程確立(參見S.R.Colby,"Calculating Synergistic and Antagonistic Responses of Herbicide Combinations",Weeds,1967,15,20－22)： Synergism is described as "the synergistic effect of the two components in the mixture, so that the overall effect is greater or longer than the sum of the effects of the two (or more) separate uses" (see PMLTames, Neth. J. Plant Pathology) 1964, 70, 73-80). The synergistic effect between the two active ingredients is established by the Colby equation (see SRColby, "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weeds, 1967, 15, 20-22):

使用Colby之方法，兩種活性成份間之增效相互作用之存在藉由首先基於單獨施用兩種組份之活性來計算混合物之預測活性p來確定。若p低於實驗確定效應，即出現增效作用。若p等於或高於實驗確定效應，則兩種成份間之相互作用定性為僅為相加或拮抗作用。在上述方程中，A為比率x下一種組份單獨施用之觀察結果。B項為率y下第二組份施用之觀察結果。該方程估算出p值，比率x之A與比率y之B之混合物的觀察結果(若其效應為精確相加且未出現相互作用)。為使用Colby方程，將混合物之活性成份在測試中獨立施用且組合施用。Using Colby's method, the presence of a synergistic interaction between the two active ingredients was determined by first calculating the predicted activity p of the mixture based on the activity of the two components administered separately. If p is lower than the experimentally determined effect, synergism occurs. If p is equal to or higher than the experimentally determined effect, the interaction between the two components is characterized only by addition or antagonism. In the above equation, A is the observation that the single component of the ratio x is administered alone. Item B is the observation of the application of the second component at rate y. This equation estimates the observation of a p-value, a mixture of the ratio x of A and the ratio y of B (if the effects are exactly additive and no interaction occurs). To use the Colby equation, the active ingredients of the mixture were applied separately in the test and administered in combination.

以下測試證明本發明之化合物、混合物或組合物對特定害蟲之控制功效。然而由該等化合物、混合物或組合物提供的害蟲控制保護作用不限於此等種類。在某些實例中，發現本發明之化合物與其他無脊椎害蟲控制化合物或藥劑之組合展示出對抗某些重要無脊椎害蟲的增效作用。The following tests demonstrate the control efficacy of the compounds, mixtures or compositions of the invention against particular pests. However, the pest control protection provided by such compounds, mixtures or compositions is not limited to such species. In certain instances, it has been discovered that the compounds of the invention in combination with other invertebrate pest control compounds or agents exhibit synergistic effects against certain important invertebrate pests.

該等混合物或組合物間之增效作用或拮抗作用的分析使用Colby方程來確定。將單獨測試化合物之平均死亡率%資料代入Colby方程中。若所觀察(obs)平均死亡率%高於"p"(預期死亡率%)，則該混合物或組合物具有增效作用。若所觀察平均死亡率%等於或低於預期死亡率，則該混合物或組合物不具有增效作用或具有拮抗作用。關於化合物說明參見索引表A。以下縮寫用於如下索引表中：Me為甲基且CN為氰基。縮寫"Ex."表示"實例"且後接一數字表示該化合物在哪一實例中製備。Analysis of synergism or antagonism between such mixtures or compositions was determined using the Colby equation. The average mortality % data for individual test compounds was substituted into the Colby equation. If the observed mean (obs) mean mortality is higher than "p" (expected mortality %), the mixture or composition has a synergistic effect. If the observed mean mortality % is equal to or lower than the expected mortality, the mixture or composition does not have a synergistic effect or has an antagonistic effect. See Index Table A for a description of the compounds. The following abbreviations are used in the following index tables: Me is methyl and CN is cyano. The abbreviation "Ex." means "instance" and followed by a number indicating in which instance the compound was prepared.

索引表B 化合物編號1 H NMR資料(除非另外指出否則均為CDCl3 溶液)a 4 δ 9.76(s,1H),8.42(m,1H),7.81(m,1H),7.32(m,1H),7.24(m,2H),7.17(s,1H),6.97(m,1H),4.89(m,1H),4.61(m,1H),4.41(m,1H),3.60(m,1H),3.49(m,1H),2.62(m,1H),2.41(m,1H)。5 δ 10.1(br s,1H),8.43(m,1H),7.82(m,1H),7.35(m,1H),7.23(m,2H),7.09(br s,1H),6.84(m,1H),4.92(m,1H),4.64(m,1H),4.44(m,1H),3.67(m,1H),3.53(m,1H),2.65(m,1H),2.41(m,1H),2.14(s,3H). 6 δ 9.75(s,1H),8.41(m,1H),7.80(m,1H),7.31(m,1H),7.21(s,2H),7.05(m,2H),4.88(m,1H),4.61(m,1H),4.41(m,1H),3.59(m,1H),3.48(m,1H)2.62(m,1H),2.41(m,1H)。7 δ 10.6(s,1H),7.65(br s,1H),7.57(br s,1H),7.51(m,1H),7.43(m,3H),7.29(br s,1H),7.04(m,1H),4.95(m,1H),4.67(m,1H),4.48(m,1H),3.68(m,1H),3.58(m,1H),2.68(m,1H),2.43(m,1H),2.49(s,3H). 8 δ 10.5(s,1H),8.44(m,1H),7.84(m,1H),7.64(m,1H),7.56(m,1H),7.37(m,1H),7.05(m,2H),4.95(m,1H),4.66(m,1H),4.48(m,1H),3.70(m,1H),3.58(m,1H),2.69(m,1H),2.43(m,1H),2.23(s,3H).a 1 H NMR資料以四甲基矽烷之低磁場ppm為單位。偶合由(s)－單峰，(d)－雙重峰，(t)－三重峰，(q)－四重峰，(m)－多重峰，(dd)－兩組雙重峰，(dt)－兩組三重峰，(br s)－寬單峰指定。 Index Table B Compound No. 1 H NMR data (both CDCl 3 solution unless otherwise indicated) a 4 δ 9.76 (s, 1H), 8.42 (m, 1H), 7.81 (m, 1H), 7.32 (m, 1H) , 7.24 (m, 2H), 7.17 (s, 1H), 6.97 (m, 1H), 4.89 (m, 1H), 4.61 (m, 1H), 4.41 (m, 1H), 3.60 (m, 1H), 3.49 (m, 1H), 2.62 (m, 1H), 2.41 (m, 1H). 5 δ 10.1(br s,1H), 8.43 (m,1H), 7.82 (m,1H), 7.35 (m,1H), 7.23 (m,2H), 7.09 (br s,1H), 6.84 (m, 1H), 4.92 (m, 1H), 4.64 (m, 1H), 4.44 (m, 1H), 3.67 (m, 1H), 3.53 (m, 1H), 2.65 (m, 1H), 2.41 (m, 1H) ), 2.14(s,3H). 6 δ 9.75(s,1H), 8.41(m,1H), 7.80(m,1H), 7.31(m,1H),7.21(s,2H),7.05(m, 2H), 4.88 (m, 1H), 4.61 (m, 1H), 4.41 (m, 1H), 3.59 (m, 1H), 3.48 (m, 1H), 2.62 (m, 1H), 2.41 (m, 1H) . 7 δ 10.6(s,1H), 7.65(br s,1H), 7.57(br s,1H),7.51(m,1H),7.43(m,3H), 7.29(br s,1H),7.04(m , 1H), 4.95 (m, 1H), 4.67 (m, 1H), 4.48 (m, 1H), 3.68 (m, 1H), 3.58 (m, 1H), 2.68 (m, 1H), 2.43 (m, 1H), 2.49(s, 3H). 8 δ 10.5(s, 1H), 8.44 (m, 1H), 7.84 (m, 1H), 7.64 (m, 1H), 7.56 (m, 1H), 7.37 (m) , 1H), 7.05 (m, 2H), 4.95 (m, 1H), 4.66 (m, 1H), 4.48 (m, 1H), 3.70 (m, 1H), 3.58 (m, 1H), 2.69 (m, 1H), 2.43 (m, 1H), 2.23 (s, 3H). The a 1 H NMR data is in the low magnetic field ppm of tetramethyl decane. Coupling consists of (s)-single peak, (d)-doublet, (t)-triplet, (q)-quadruple, (m)-multiplet, (dd)-two sets of doublet, (dt) - Two sets of triplet, (br s) - wide single peak designation.

本發明之生物學實例Biological example of the invention

測試A 對於評估對小菜蛾(Plutella xylostella )之控制，測試單元由其內具有12－14日齡之蘿蔔植株的小開口容器組成。用一片昆蟲餌料上之10－15個新生幼蟲來預侵擾此測試單元，其藉由下列過程來完成：使用岩心取樣器將一塞自一片具有許多生長於其上之幼蟲的硬化昆蟲餌料中移除且將含有幼蟲及餌料之塞轉移至測試單元。當餌料塞變乾時幼蟲轉移至測試植株上。 Test A For the evaluation of control of Plutella xylostella , the test unit consisted of a small open container with radish plants of 12-14 days old. The test unit is pre-infested with 10-15 newborn larvae on a piece of insect bait by the following process: using a core sampler to move a plug from a hardened insect bait with many larvae grown thereon In addition to transferring the plug containing the larvae and bait to the test unit. The larvae were transferred to the test plants as the bait plugs dry.

使用含有10%丙酮、90%水之溶液及含有烷基芳基聚氧乙烯、游離脂肪酸、乙二醇及2－丙醇之300 ppm X－77T M Spreader Lo－Foam Formula非離子界面活性劑(Loveland Industries，Inc.Greeley,Colorado,USA)來調配測試化合物或混合物。經由位於各自測試單元頂部之上1.27厘米(0.5英吋)處的具有1/8 JJ慣體(custom body)之SUJ2霧化噴嘴(Spraying Systems Co.Wheaton,Illinois,USA)以1 mL液體來施用經調配之化合物或混合物。以10 ppm噴霧此等測試中之所有實驗化合物，重複3次。對於此等測試中之實驗混合物而言，為獲得所要的各化合物之混合物濃度，將兩倍所要濃度之各兩種混合搭配化合物以相等體容混合在一起。300 ppm X-77 T M Spreader Lo-Foam Formula nonionic surfactant containing 10% acetone, 90% water and alkyl aryl polyoxyethylene, free fatty acid, ethylene glycol and 2-propanol (Loveland Industries, Inc. Greeley, Colorado, USA) to formulate test compounds or mixtures. Application was carried out with 1 mL of liquid via a SUJ2 atomizing nozzle (Spraying Systems Co. Wheaton, Illinois, USA) with 1/8 JJ custom body at 1.27 cm (0.5 inch) above the top of the respective test unit. A compound or mixture that is formulated. All test compounds in these tests were sprayed at 10 ppm and repeated 3 times. For the experimental mixtures in these tests, in order to obtain the desired mixture concentration of each compound, two mixed compoundes of twice the desired concentration were mixed together in an equal body.

在噴霧經調配之測試化合物或混合物後，允許各測試單元乾燥1小時且接著將黑色遮蔽蓋置放於其上。將測試單元保持於25℃及70%相對濕度之生長箱中持續6天。接著基於被食用之葉片來目測評定植株的給食損害。After spraying the formulated test compound or mixture, each test unit was allowed to dry for 1 hour and then a black mask was placed thereon. The test unit was kept in a growth chamber at 25 ° C and 70% relative humidity for 6 days. The feeding damage of the plants was then assessed visually based on the leaves being eaten.

在經測試之式1化合物中，下列提供極佳至優秀的植株保護水平(20%或更低之給食損害)：1、2及3。Among the compounds of formula 1 tested, the following provides excellent to excellent plant protection levels (feed damage of 20% or less): 1, 2 and 3.

對於所測試混合物之結果列於表A1中。"＊ "指示所觀察保護%高於由Colby方程所計算之保護%。The results for the tested mixtures are listed in Table A1. " * " indicates that the % of protection observed is higher than the % of protection calculated by the Colby equation.

測試B 對於評估對草地黏蟲(Spodoptera frugiperda )之控制，測試單元由其內具有4－5日齡之穀物(玉米)植株的小開口容器組成。用一片昆蟲餌料上之10－15個1日齡之幼蟲來預侵擾(使用岩心取樣器)此測試單元。 Test B For the evaluation of control of the grass worm ( Spodoptera frugiperda ), the test unit consisted of a small open container with 4-5 day old grain (corn) plants. The test unit was pre-infested (using a core sampler) with 10-15 1 day old larvae on a piece of insect bait.

如測試A所述調配測試化合物1、2及3且以10 ppm進行噴霧。重複施用3次。如測試A所述在噴霧之後，將測試單元維持於生長箱中且接著進行目測評定。Test compounds 1, 2 and 3 were formulated as described in Test A and sprayed at 10 ppm. Repeat the application 3 times. After the spray as described in Test A, the test unit was maintained in a growth chamber and then visually assessed.

在經測試之式1化合物中，下列提供極佳至優秀的植株保護水平(20%或更低之給食損害)：1、2、3、4、5、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24、25、26、27、28、29、30及31。Among the compounds of formula 1 tested, the following provides excellent to excellent plant protection levels (feed damage of 20% or less): 1, 2, 3, 4, 5, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, and 31.

測試C 對於經由接觸及/或系統方法來評估對桃蚜(Myzus persicae )之控制，測試單元由其內具有12至15日齡之蘿蔔植株的小開口容器組成。藉由將一片切離自培養植株之葉片上的30－40個幼蟲置放於測試植株之葉片上來預侵擾此測試單元(切葉方法)。當葉片乾燥時幼蟲轉移至測試植株上。在預侵擾之後，以沙層來覆蓋測試單元之土壤。 Test C For the control of Myzus persicae via a contact and/or system approach, the test unit consisted of a small open container with radish plants of 12 to 15 days old. The test unit was pre-infested by placing a piece of 30-40 larvae cut off from the leaves of the cultured plants on the leaves of the test plants (cutting method). The larvae were transferred to the test plants as the leaves dried. After the pre-infestation, the soil of the test unit is covered with a sand layer.

如測試A所述調配所有測試化合物且以50 ppm進行噴霧且重複3次。如測試A所述調配測試混合物且重複3次。在噴霧經調配之測試化合物或混合物後，允許各自測試單元乾燥1小時且接著將黑色遮蔽蓋置放於其上。將測試單元保持於19－21℃及50－70%相對濕度之生長箱中持續6天。計數各測試單元中蚜蟲之死亡數目及總數目以確定死亡百分率。All test compounds were formulated as described in Test A and sprayed at 50 ppm and repeated 3 times. The test mixture was formulated as described in Test A and repeated 3 times. After spraying the formulated test compound or mixture, the respective test units were allowed to dry for 1 hour and then the black masking cover was placed thereon. The test unit was maintained in a growth chamber at 19-21 ° C and 50-70% relative humidity for 6 days. The number and total number of mites in each test unit were counted to determine the percentage of death.

在經測試之式1 化合物中，下列導致至少80%之死亡率：1、3、4、6、8、9、10、11及12。In the compounds of formula 1 tested, the following resulted in at least 80% mortality: 1, 3, 4, 6, 8, 9, 10, 11 and 12.

對於所測試混合物之結果列於表C1中。"＊ "指示所觀察死亡率%高於由Colby方程所計算之死亡率%。The results for the tested mixtures are listed in Table C1. " * " indicates that the observed mortality % is higher than the % mortality calculated by the Colby equation.

測試D 為經由接觸及/或系統方法來評估對蠶豆微葉蟬(Empoasca fabae )之控制，測試單元由其內具有5至6日齡之Longio豆植株(出現首葉)的小開口容器組成。將白沙施加於土壤之上，且在施用前切離一片首葉。如測試A所述調配測試化合物且以50 ppm進行噴霧且重複3次。噴霧後，允許測試單元乾燥1小時且接著以5隻蠶豆微葉蟬(18至21日齡成蟲)後侵擾。將黑色遮蔽蓋置放於圓柱之上。將測試單元保持於19－21℃及50－70%相對濕度之生長箱中持續6天。接著對各測試單元目測評估昆蟲死亡率。 Test D is a control of the control of the broad bean mites (Eposoca fabae ) via a contact and/or system method consisting of a small open container having 5 to 6 day old Longio bean plants (with apical leaves). White sand was applied to the soil and one of the first leaves was cut off prior to application. Test compounds were formulated as described in Test A and sprayed at 50 ppm and repeated 3 times. After spraying, the test unit was allowed to dry for 1 hour and then infested with 5 broad bean microlobules (18 to 21 day old adults). Place the black shade cover over the cylinder. The test unit was maintained in a growth chamber at 19-21 ° C and 50-70% relative humidity for 6 days. The insect mortality was then visually assessed for each test unit.

在所測試之式1化合物中，下列導致至少80%之死亡率：2、3、9、10及11。Among the compounds of formula 1 tested, the following resulted in at least 80% mortality: 2, 3, 9, 10 and 11.

測試E 為經由接觸及/或系統方法來評估對棉蚜(Aphis gossypii )之控制，測試單元由其中具有6至7日齡之棉花植株的小開口容器組成。根據測試C所述之切葉法以一片葉上之30－40隻昆蟲來預侵擾此測試單元，且將測試單元之土壤用一層沙覆蓋。如測試A所述調配測試化合物且以50 ppm進行噴霧。該等施用重複3次。如測試A所述，噴霧後將測試單元維持於生長箱中接著目測評定等級。 Test E is the evaluation of control of cotton aphid ( Aphis gossypii ) via a contact and/or system method consisting of a small open container having 6 to 7 day old cotton plants therein. The test unit was pre-infested with 30-40 insects on one leaf according to the leaf cutting method described in Test C, and the soil of the test unit was covered with a layer of sand. Test compounds were formulated as described in Test A and sprayed at 50 ppm. These applications were repeated 3 times. As described in Test A, the test unit was maintained in the growth chamber after spraying and then visually rated.

在所測試之式1化合物中，下列導致至少80%之死亡率：1、2、3、4、5、6、8、9、10及11。Of the compounds of formula 1 tested, the following resulted in at least 80% mortality: 1, 2, 3, 4, 5, 6, 8, 9, 10 and 11.

測試F 為經由接觸及/或系統方法來評估對對玉米飛虱(Peregrinus maidis )之控制，測試單元由其內具有3至4日齡之穀物(玉米)植株(穗)的小開口圓柱容器組成。在施用前將白沙添加至土壤之上。如測試A所述調配測試混合物且進行噴霧，重複3次。噴霧後，允許測試單元乾燥1小時且接著藉由以鹽瓶將10至20隻玉米飛虱(18至20日齡若蟲)撒於沙上來用其進行後侵擾。將黑色遮蔽蓋置放於各容器之上。將測試單元保持於19－21℃及50－70%相對濕度之生長箱中持續6天。計數各測試單元中玉米飛虱之死亡數目及總數目以確定死亡百分率。 Test F is the evaluation of control of the corn borer ( Peregrinus maidis ) via a contact and/or system method consisting of a small open cylindrical container having 3 to 4 day old grain (corn) plants (ears) . White sand was added to the soil prior to application. The test mixture was formulated as described in Test A and sprayed, repeated 3 times. After spraying, the test unit was allowed to dry for 1 hour and then post-infestation was carried out by sprinkling 10 to 20 corn planthoppers (18 to 20 day old nymphs) on sand with a salt shaker. Place the black shade cover over each container. The test unit was maintained in a growth chamber at 19-21 ° C and 50-70% relative humidity for 6 days. The number and total number of deaths of corn locusts in each test unit were counted to determine the percentage of death.

對於所測試混合物之結果列於表F1中。"＊ "指示所觀察死亡率%高於由Colby方程所計算之死亡率%。The results for the tested mixtures are listed in Table F1. " * " indicates that the observed mortality % is higher than the % mortality calculated by the Colby equation.

測試G 為經由接觸及/或系統方法來評估對苜蓿薊馬(Frankliniella occidentalis Pergande)之控制，各測試單元由其內具有5至7日齡之豆(var.Soleil)植株的小開口容器組成。 Test G is the control of the control of the scorpion ( Frankliniella occidentalis Pergande) by contact and/or system methods, each test unit consisting of a small open container having 5 to 7 day old beans (var. Soleil) plants.

如測試A所述調配測試混合物且進行噴霧，重複3次。噴霧後，允許測試單元乾燥1小時，將22至27隻薊馬成蟲添加至各單元且接著將黑色遮蔽蓋置放於其上。將測試單元保持於25℃及45－55%相對濕度下持續7天。評定各測試單元之植株受損量以確定植物保護百分率。The test mixture was formulated as described in Test A and sprayed, repeated 3 times. After spraying, the test unit was allowed to dry for 1 hour, 22 to 27 adult thrips were added to each unit and then a black mask was placed thereon. The test unit was maintained at 25 ° C and 45-55% relative humidity for 7 days. The amount of plant damage per test unit was assessed to determine the percentage of plant protection.

對於所測試混合物之結果列於表G1中。"＊ "指示所觀察保護%高於由Colby方程所計算之保護%。The results for the tested mixtures are listed in Table G1. " * " indicates that the % of protection observed is higher than the % of protection calculated by the Colby equation.

Claims (33)

一種式1 之化合物、其N -氧化物或鹽， 其中：J 為： R1a 為C1 -C6 烷基、C2 -C6 烯基、C2 -C6 炔基、C3 -C6 環烷基、C1 -C6 鹵烷基、C2 -C6 鹵烯基、C2 -C6 鹵炔基、C3 -C6 鹵環烷基、鹵素、CN、CHO、NO2 、C1 -C4 烷氧基、C1 -C4 鹵烷氧基、C1 -C4 烷基硫基、C1 -C4 烷基亞磺醯基、C1 -C4 烷基磺醯基、C1 -C4 鹵烷基硫基、C1 -C4 鹵烷基亞磺醯基、C1 -C4 鹵烷基磺醯基、C2 -C4 烷基羰基、C2 -C4 烷氧基羰基、C2 -C4 烷基胺基羰基、C3 -C5 二烷基胺基羰基、C1 -C4 烷基胺基或C2 -C6 二烷基胺基；R1b 為H、C1 -C6 烷基、C2 -C6 烯基、C2 -C6 炔基、C3 -C6 環烷基、C1 -C6 鹵烷基、C2 -C6 鹵烯基、C2 -C6 鹵炔基、C3 -C6 鹵環烷基、鹵素、CN、CHO、NO2 、C1 -C4 烷氧基、C1 -C4 鹵烷氧基、C1 -C4 烷基硫基、C1 -C4 烷基亞磺醯基、C1 -C4 烷基磺醯基、C1 -C4 鹵烷基硫基、C1 -C4 鹵烷基亞磺醯基、C1 -C4 鹵烷基磺醯基、C2 -C4 烷基羰基、C2 -C4 烷氧基羰基、C2 -C4 烷基胺基羰基、C3 -C5 二烷基胺基羰基、C1 -C4 烷基胺基或C2 -C6 二烷基胺基；R2 為H；或C1 -C6 烷基、C2 -C6 烯基、C2 -C6 炔基或C3 -C6 環烷基，各視情況經一或多個選自由鹵素、CN、NO2 、羥基、C1 -C4 烷基、C1 -C4 烷氧基、C1 -C4 烷基硫基、C1 -C4 烷基亞磺醯基、C1 -C4 烷基磺醯基、C2 -C4 烷氧基羰基、C1 -C4 烷基胺基、C2 -C8 二烷基胺基及C3 -C6 環烷基胺基組成之群之取代基取代；或R2 為C2 -C6 烷基羰基、C2 -C6 烷氧基羰基、C2 -C6 烷基胺基羰基或C3 -C8 二烷基胺基羰基；R3 為H、C1 -C6 烷基、C2 -C6 烯基、C2 -C6 炔基、C3 -C6 環烷基、C1 -C4 烷氧基、C1 -C4 烷基胺基、C2 -C8 二烷基胺基、C3 -C6 環烷基胺基、C2 -C6 烷氧基羰基或C2 -C6 烷基羰基；R4 為C5 -C12 烯基環烷基、C5 -C12 炔基環烷基、C4 -C12 環烷基烷基、C5 -C12 環烷基烯基、C5 -C12 環烷基炔基、C4 -C12 環烯基烷基或C4 -C12 烷基環烯基，各視情況經1至6個選自CH3 及鹵素之取代基取代；或R4 為C3 -C5 環氧乙烷基烷基、C3 -C5 硫雜環丙烷基烷基、C4 -C6 環氧丙烷基烷基、C4 -C6 硫雜環丁烷基烷基、3- 環氧丙烷基或3-硫雜環丁烷基，各視情況經1至5個獨立選自C1 -C3 烷基、C1 -C3 鹵烷基、鹵素、CN、C2 -C4 烷氧基羰基及C2 -C4 鹵烷氧基羰基之取代基取代；或R4 為C3 -C5 吖丙啶基烷基、C4 -C6 吖丁啶基烷基或3-吖丁啶基，其經連接至氮原子之R10 取代，且視情況在碳原子上經1至5個獨立選自C1 -C3 烷基、C1 -C3 鹵烷基、鹵素、CN、C2 -C4 烷氧基羰基及C2 -C4 鹵烷氧基羰基之取代基取代；R6 獨立選自由H、C1 -C6 烷基、C3 -C6 環烷基、C1 -C6 鹵烷基、鹵素、CN、C1 -C4 烷氧基、C2 -C4 烷氧基羰基、C1 -C4 烷基硫基、C1 -C4 鹵烷氧基、C1 -C4 鹵烷基硫基、C1 -C4 鹵烷基亞磺醯基及C1 -C4 鹵烷基磺醯基組成之群；R7 為視情況經一或多個選自由鹵素、CN、NO2 、羥基、C1 -C4 烷氧基、C1 -C4 烷基硫基、C1 -C4 烷基亞磺醯基、C1 -C4 烷基磺醯基、C2 -C4 烷氧基羰基、C1 -C4 烷基胺基、C2 -C8 二烷基胺基及C3 -C6 環烷基胺基組成之群之取代基取代的C1 -C6 烷基；或視情況經1至3個選自R9 之取代基取代的苯基；或R7 為 各R9 獨立為C1 -C6 烷基、C3 -C6 環烷基、C1 -C6 鹵烷基、鹵素、CN、C1 -C4 烷氧基、C1 -C4 烷基硫基、C1 -C4 鹵烷 氧基、C1 -C4 鹵烷基硫基、C1 -C4 鹵烷基亞磺醯基或C1 -C4 鹵烷基磺醯基；R10 為H、C1 -C3 烷基、C1 -C3 鹵烷基、C2 -C4 烷基羰基、C2 -C4 鹵烷基羰基、C2 -C4 烷氧基羰基或C1 -C3 烷基磺醯基；且s為0、1或2；限制條件為：式1 之化合物不為3-溴-1-(3-氯-2-吡啶基)-N -[4-氰基-2-[[(環丙基甲基)胺基]羰基]-6-甲基苯基]-1H -吡唑-5-甲醯胺。a compound of formula 1 , an N -oxide or a salt thereof, Where: J is: R 1a is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 Haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, CN, CHO, NO 2 , C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy , C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 Haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkoxycarbonyl, C 2 -C 4 alkylaminocarbonyl, C 3 -C 5 dialkylaminocarbonyl, C 1 -C 4 alkylamino or C 2 -C 6 dialkylamino; R 1b is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, CN, CHO, NO 2 , C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 halo Sulfosyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkoxycarbonyl a C 2 -C 4 alkylaminocarbonyl group, a C 3 -C 5 dialkylaminocarbonyl group, a C 1 -C 4 alkylamino group or a C 2 -C 6 dialkylamino group; R 2 is H Or a C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group or a C 3 -C 6 cycloalkyl group, each optionally selected from the group consisting of halogen, CN, NO 2 , hydroxy, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkyl Substitution of a group consisting of a sulfonyl group, a C 2 -C 4 alkoxycarbonyl group, a C 1 -C 4 alkylamino group, a C 2 -C 8 dialkylamino group, and a C 3 -C 6 cycloalkylamine group Substituted; or R 2 is C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl or C 3 -C 8 dialkylaminocarbonyl; R 3 is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 1 -C a 4- alkylamino group, a C 2 -C 8 dialkylamino group, a C 3 -C 6 cycloalkylamino group, a C 2 -C 6 alkoxycarbonyl group or a C 2 -C 6 alkylcarbonyl group; R 4 is C 5 -C 12 alkenylcycloalkyl, C 5 -C 12 alkynylcycloalkyl, C 4 -C 12 cycloalkylalkyl, C 5 -C 12 cycloalkylalkenyl, C 5 -C 12 ring Alkynyl group, C 4- C 12 cycloalkenylalkyl or C 4 -C 12 alkylcycloalkenyl, each optionally substituted with 1 to 6 substituents selected from CH 3 and halogen; or R 4 is C 3 -C 5 ring Oxyethanealkyl, C 3 -C 5 thicyclopropylalkyl, C 4 -C 6 epoxypropanealkyl, C 4 -C 6 thietanealkyl, 3-epoxy Propane or 3-thietane, each optionally 1 to 5 independently selected from C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, halogen, CN, C 2 -C 4 alkane Substituted with a substituent of an oxycarbonyl group and a C 2 -C 4 haloalkoxycarbonyl group; or R 4 is a C 3 -C 5 aziridinylalkyl group, a C 4 -C 6 azetidinylalkyl group or a 3-azetidinyl group, It is substituted by R 10 attached to a nitrogen atom, and optionally from 1 to 5 independently selected from C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, halogen, CN, C 2 - on the carbon atom. Substituted with a C 4 alkoxycarbonyl group and a C 2 -C 4 haloalkoxycarbonyl group; R 6 is independently selected from H, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, halogen, CN, C 1 -C 4 alkoxy, C 2 -C 4 alkoxycarbonyl, C 1 -C 4 alkylthio, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkyl thio, C 1 -C 4 alkylsulfinyl acyl halide Group C 1 -C 4 haloalkyl group consisting of sulfo acyl; R 7 is optionally substituted with one or more selected from the group consisting of halogen, CN, NO 2, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 Alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkoxycarbonyl, C 1 -C 4 alkylamino, C 2 a C 1 -C 6 alkyl group substituted with a substituent of a group consisting of a C 8 dialkylamino group and a C 3 -C 6 cycloalkylamino group; or optionally 1 to 3 substituents selected from R 9 Substituted phenyl; or R 7 is Each R 9 is independently C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, halogen, CN, C 1 -C 4 alkoxy, C 1 -C 4 alkane Thiothio, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl or C 1 -C 4 haloalkylsulfonyl; R 10 is H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 haloalkylcarbonyl, C 2 -C 4 alkoxycarbonyl Or C 1 -C 3 alkylsulfonyl; and s is 0, 1 or 2; the restriction is that the compound of formula 1 is not 3-bromo-1-(3-chloro-2-pyridyl) -N - [4-Cyano-2-[[(cyclopropylmethyl)amino]carbonyl]-6-methylphenyl]-1 H -pyrazole-5-carboxamide. 如請求項1之化合物，其中：R1a 為C1 -C4 烷基、C1 -C4 鹵烷基、鹵素、CN、NO2 、C1 -C4 烷氧基、C1 -C4 鹵烷氧基、C1 -C4 烷基硫基、C1 -C4 烷基亞磺醯基、C1 -C4 烷基磺醯基、C1 -C4 鹵烷基硫基、C1 -C4 鹵烷基亞磺醯基或C1 -C4 鹵烷基磺醯基；R1b 為H、C1 -C4 烷基、C1 -C4 鹵烷基、鹵素、CN、NO2 、C1 -C4 烷氧基、C1 -C4 鹵烷氧基、C1 -C4 烷基硫基、C1 -C4 烷基亞磺醯基、C1 -C4 烷基磺醯基、C1 -C4 鹵烷基硫基、C1 -C4 鹵烷基亞磺醯基或C1 -C4 鹵烷基磺醯基；R2 及R3 各自獨立為H、C1 -C4 烷基、C2 -C4 烯基、C2 -C4 炔基、C3 -C6 環烷基、C2 -C6 烷基羰基或C2 -C6烷氧基羰基；且R4 為C4 -C12 環烷基烷基，各視情況經1至6個選自CH3 及鹵素之取代基取代；或R4 為C3 -C5 環氧乙烷基烷基、C4 -C6 環氧丙烷基烷基或3-環 氧丙烷基，各視情況經1至2個獨立選自CH3 、CF3 、鹵素、CN及C(O)OCH3 之取代基取代。The compound of claim 1, wherein: R 1a is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halogen, CN, NO 2 , C 1 -C 4 alkoxy, C 1 -C 4 Haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl or C 1 -C 4 haloalkylsulfonyl; R 1b is H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halogen, CN, NO 2 , C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkane Sulfosyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl or C 1 -C 4 haloalkylsulfonyl; R 2 and R 3 are each independently H , C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkylcarbonyl or C 2 -C6 alkoxy a carbonyl group; and R 4 is a C 4 -C 12 cycloalkylalkyl group, each optionally substituted with 1 to 6 substituents selected from CH 3 and halogen; or R 4 is a C 3 -C 5 oxiranyl group An alkyl group, a C 4 -C 6 epoxypropenylalkyl group or a 3-epoxypropane group, optionally 1 to 2 independently selected from the group consisting of CH 3 , CF 3 , halogen, CN and C(O)OCH 3 of substituents. 如請求項2之化合物，其中：R1a 為CH3 、CF3 、OCF3 、OCHF2 、S(O)n CF3 、S(O)n CHF2 、CN或鹵素；R1b 為H、CH3 、CF3 、OCF3 、OCHF2 、S(O)p CF3 、S(O)p CHF2 、CN或鹵素；R2 及R3 為H；n為0、1或2；且p為0、1或2。The compound of claim 2, wherein: R 1a is CH 3 , CF 3 , OCF 3 , OCHF 2 , S(O) n CF 3 , S(O) n CHF 2 , CN or halogen; R 1b is H, CH 3 , CF 3 , OCF 3 , OCHF 2 , S(O) p CF 3 , S(O) p CHF 2 , CN or halogen; R 2 and R 3 are H; n is 0, 1 or 2; and p is 0, 1 or 2. 如請求項3之化合物，其中：R6 獨立為H、CH3 、CF3 、CH2 CF3 、CHF2 、OCH2 CF3 、OCHF2 或鹵素；R7 為視情況經1至3個選自R9 之取代基取代之苯基；或R7 為 各R9 獨立為C1 -C4 烷基、C1 -C4 鹵烷基、鹵素或CN；且s為0、1或2。The compound of claim 3, wherein: R 6 is independently H, CH 3 , CF 3 , CH 2 CF 3 , CHF 2 , OCH 2 CF 3 , OCHF 2 or halogen; R 7 is optionally selected from 1 to 3 a phenyl group substituted with a substituent of R 9 ; or R 7 is Each R 9 is independently C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halogen or CN; and s is 0, 1 or 2. 如請求項4之化合物，其中：R6 獨立為鹵素、OCH2 CF3 、OCHF2 或CF3 ；R7 為或；且各R9 獨立為H、CH3 、CF3 、CN或鹵素。The compound of claim 4, wherein: R 6 is independently halogen, OCH 2 CF 3 , OCHF 2 or CF 3 ; R 7 is or And each R 9 is independently H, CH 3 , CF 3 , CN or halogen. 如請求項5之化合物，其中：R1a 為CH3 、F、Cl、Br或I；R1b 為H、CH3 、CF3 、CN、F、Cl、Br或I；且各R6 獨立為Cl、Br、OCH2 CF3 或CF3 。The compound of claim 5, wherein: R 1a is CH 3 , F, Cl, Br or I; R 1b is H, CH 3 , CF 3 , CN, F, Cl, Br or I; and each R 6 is independently Cl, Br, OCH 2 CF 3 or CF 3 . 如請求項6之化合物，其中：R4 為環丙基甲基或環丁基甲基；各視情況經1至4個CH3 或鹵素取代；或R4 為環氧乙烷基甲基、2-環氧丙烷基甲基、3-環氧丙烷基甲基或3-環氧丙烷基，各視情況經1至2個CH3 取代。The compound of claim 6, wherein: R 4 is cyclopropylmethyl or cyclobutylmethyl; each optionally substituted with 1 to 4 CH 3 or halogen; or R 4 is oxiranylmethyl, 2- A propylene oxide methyl group, a 3-epoxypropanemethyl group or a 3-epoxypropane group, each optionally substituted with 1 to 2 CH 3 . 如請求項1之化合物，其係選自由以下化合物組成之群：1-(3-氯-2-吡啶基)-N -[4-氰基-2-[[(環丙基甲基)胺基]羰基]-6-甲基苯基]-3-(三氟甲基)-1H -吡唑-5-甲醯胺；3-溴-N -[4-氯-2-[[(環丙基甲基)胺基]羰基]-6-甲基苯基]-1-(3-氯-2-吡啶基)-1H -吡唑-5-甲醯胺；3-溴-1-(3-氯-2-吡啶基)-N -[2,4-二氯-6-[[(2-環氧丙烷基甲基)胺基]羰基]苯基]-1H -吡唑-5-甲醯胺；3-溴-N -[4-氯-2-甲基-6-[[(2-環氧丙烷基甲基)胺基]羰基]苯基]-1-(3-氯-2-吡啶基)-1H -吡唑-5-甲醯胺；3-氯-1-(3-氯-2-吡啶基)-N -[2,4-二氯-6-[[(2-環氧丙烷 基甲基)胺基]羰基]苯基]-1H -吡唑-5-甲醯胺；1-(2-氯苯基)-N -[4-氰基-2-甲基-6-[[(2-環氧丙烷基甲基)胺基]羰基]苯基]-3-(三氟甲基)-1H -吡唑-5-甲醯胺；3-溴-1-(3-氯-2-吡啶基)-N -[4-氰基-2-甲基-6-[[(2-環氧丙烷基甲基)胺基]羰基]苯基]-1H -吡唑-5-甲醯胺；3-溴-N -[4-氯-2-甲基-6-[[(1-甲基環丙基)胺基]羰基]苯基]-1-(3-氯-2-吡啶基)-1H -吡唑-5-甲醯胺；3-溴-1-(2-氯苯基)-N -[4-氰基-2-[[(環丙基甲基)胺基]羰基]-6-甲基苯基]-1H -吡唑-5-甲醯胺；3-溴-N -[4-氯-2-[[(環丙基甲基)胺基]羰基]-6-甲基苯基]-1-(2-氯苯基)-1N -吡唑-5-甲醯胺；3-溴-N -[4-氯-2-[[(1-環丙基乙基)胺基]羰基]-6-甲基苯基]-1-(3-氯-2-吡啶基)-1H -吡唑-5-甲醯胺；3-溴-N -[4-氯-2-[[(1-環丙基乙基)胺基]羰基]-6-甲基苯基]-1-(2-氯苯基)-1H -吡唑-5-甲醯胺；及3-溴-1-(3-氯-2-吡啶基)-N -[4-氰基-2-[[(1-環丙基乙基)胺基]羰基]-6-甲基苯基]-1H -吡唑-5-甲醯胺。The compound of the requested item 1, the composition of the group selected from the group consisting of the following compound which is: 1- (3-chloro-2-pyridinyl) - N - [4- cyano-2 - [[(cyclopropylmethyl) amine (carbonyl)-6-methylphenyl]-3-(trifluoromethyl)-1 H -pyrazole-5-carboxamide; 3-bromo- N- [4-chloro-2-[[( Cyclopropylmethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridyl)-1 H -pyrazole-5-carboxamide; 3-bromo-1 - (3-chloro-2-pyridinyl) - N - [2,4- dichloro-6 - [[(2-oxetanylmethyl) amino] carbonyl] phenyl] -1 H - pyrazol -5-carbamide; 3-bromo- N- [4-chloro-2-methyl-6-[[(2-epoxypropenylmethyl)amino]carbonyl]phenyl]-1-(3) - chloro-2-pyridinyl) -1 H - pyrazole-5-acyl-amine; 3-chloro-1- (3-chloro-2-pyridinyl) - N - [2,4- dichloro-6- [[(2-oxetanylmethyl) amino] carbonyl] phenyl] -1 H - pyrazole-5-acyl-amine; 1- (2-chlorophenyl) - N - [4- cyano -2-methyl-6-[[(2-epoxypropenylmethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1 H -pyrazole-5-carboxamide; 3-bromo-1- (3-chloro-2-pyridinyl) - N - [4- cyano-2-methyl-6 - [[(2-oxetanylmethyl) amino] carbonyl] benzene yl] -1 H - pyrazole-5-acyl-amine; 3-bromo - N - [4- chloro-2-methyl-6 - [[(1-methylcyclopropyl) Yl] carbonyl] phenyl] -1- (3-chloro-2-pyridinyl) -1 H - pyrazole-5-acyl-amine; 3-Bromo-1- (2-chlorophenyl) - N - [ 4-cyano-2-[[(cyclopropylmethyl)amino]carbonyl]-6-methylphenyl]-1 H -pyrazole-5-carboxamide; 3-bromo- N- [4 -Chloro-2-[[(cyclopropylmethyl)amino]carbonyl]-6-methylphenyl]-1-(2-chlorophenyl)-1 N -pyrazole-5-carboxamide; 3-bromo- N- [4-chloro-2-[[(1-cyclopropylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl) -1 H -pyrazole-5-carbamidamine; 3-bromo- N- [4-chloro-2-[[(1-cyclopropylethyl)amino]carbonyl]-6-methylphenyl] 1- (2-chlorophenyl) -1 H - pyrazole-5-acyl-amine; and 3-bromo-1- (3-chloro-2-pyridinyl) - N - [4- cyano-2 -[[(1-Cyclopropylethyl)amino]carbonyl]-6-methylphenyl]-1 H -pyrazole-5-carboxamide. 一種包含請求項1之化合物及至少一選自由界面活性劑、固體稀釋劑及液體稀釋劑組成之群的額外組份之組合物，該組合物視情況另外包含至少一額外生物活性化合物或藥劑。 A composition comprising the compound of claim 1 and at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, the composition optionally further comprising at least one additional biologically active compound or agent. 一種用於控制一無脊椎害蟲之組合物，其包含生物有效量的請求項1之化合物及至少一選自由界面活性劑、固體稀釋劑及液體稀釋劑組成之群的額外組份，該組合物視 情況另外包含生物有效量的至少一額外生物活性化合物或藥劑。 A composition for controlling an invertebrate pest comprising a biologically effective amount of a compound of claim 1 and at least one additional component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, the composition Vision The condition additionally comprises a biologically effective amount of at least one additional biologically active compound or agent. 如請求項10之組合物，其中至少一額外生物活性化合物或藥劑係選自由以下殺蟲劑組成之群：合成除蟲菊酯、胺基甲酸酯、新煙鹼類似物、神經元鈉通道阻斷劑、殺昆蟲大環內酯、γ-胺基丁酸(GABA)拮抗劑、殺昆蟲脲及保幼激素模擬物、蘇力菌屬(Bacillus thuringiensis )之成員、蘇力菌δ-內毒素及天然存在或經基因修飾之病毒殺蟲劑。The composition of claim 10, wherein the at least one additional bioactive compound or agent is selected from the group consisting of pyrethroids, urethanes, neonicotinoids, neuronal sodium channels Blockers, insecticidal macrolides, gamma-aminobutyric acid (GABA) antagonists, insecticidal ureas and juvenile hormone mimetics, members of Bacillus thuringiensis , sulphate δ- Toxins and naturally occurring or genetically modified viral insecticides. 如請求項11之組合物，其中該至少一額外生物活性化合物或藥劑係選自由以下物質組成之群：阿巴汀(abamectin)、歐殺松(acephate)、亞滅培(acetamiprid)、乙醯普洛(acetoprole)、胺氟滅(amidoflumet，S-1955)、阿維菌素(avermectin)、印苦楝子素(azadirachtin)、穀硫磷(azinphos-methyl)、畢芬寧(bifenthrin)、畢芬載(bifenazate)、雙三氟蟲脲(bistrifluron)、布芬淨(buprofezin)、加保扶(carbofuran)、培丹(cartap)、克芬那比(chlorfenapyr)、克福隆(chlorfluazuron)、陶斯松(chlorpyrifos)、甲基陶斯松、環蟲醯肼(chromafenozide)、可尼丁(clothianidin)、賽扶寧(cyfluthrin)、β-賽扶寧(beta-cyfluthrin)、賽洛寧(cyhalothrin)、λ-賽洛寧(lambda-cyhalothrin)、賽滅寧(cypermethrin)、賽滅淨(cyromazine)、第滅寧(deltamethrin)、戴芬西隆(diafenthiuron)、二嗪農(diazinon)、地特靈(dieldrin)、二福隆(diflubenzuron)、樂果(dimethoate)、呋 蟲胺(dinotefuran)、戴芬蘭(diofenolan)、伊曼美丁(emamectin)、安殺番(endosulfan)、益化利(esfenvalerate)、伊希普(ethiprole)、苯硫威(fenothiocarb)、芬諾西克(fenoxycarb)、芬普寧(fenpropathrin)、芬化利(fenvalerate)、費普尼(fipronil)、氟啶蟲醯胺(flonicamid)、氟苯二醯胺(flubendiamide)、護賽寧(flucythrinate)、福化利(tau-fluvalinate)、氟魯芬(flufenerim，UR-50701)、氟芬隆(flufenoxuron)、γ-賽洛寧(gamma-cyhalothrin)、鹵芬載(halofenozide)、六伏隆(hexaflumuron)、伏蟻腙(hydramethylnon)、益達胺(imidacloprid)、茚蟲威(indoxacarb)、亞芬松(isofenphos)、祿芬隆(lufenuron)、馬拉硫磷(malathion)、麥特氟米腙(metaflumizone)、聚乙醛(metaldehyde)、甲胺磷(methamidophos)、殺撲磷(methidathion)、滅多蟲(methomyl)、美賜年(methoprene)、甲氧氯(methoxychlor)、甲氧芬載(methoxyfenozide)、甲氧苄氟菊酯(metofluthrin)、久效磷(monocrotophos)、甲氧芬載(methoxyfenozide)、烯啶蟲胺(nitenpyram)、尼賽新(nithiazine)、諾華隆(novaluron)、諾氟隆(noviflumuron，XDE-007)、歐殺滅(oxamyl)、對硫磷(parathion)、甲基對硫磷(parathion-methyl)、百滅寧(permethrin)、甲拌磷(phorate)、伏殺磷(phosalone)、亞胺硫磷(phosmet)、磷胺(phosphamidon)、抗蚜威(pirimicarb)、丙溴磷(profenofos)、丙氟菊酯(profluthrin)、普曲芬布(protrifenbute)、吡蚜酮(pymetrozine)、除蟲菊素(pyrethrin)、啶蟲丙醚(pyridalyl)、 比普西芬(pyriproxyfen)、魚藤酮(rotenone)、蘭尼定(ryanodine)、S1812(Valent)、賜諾殺(spinosad)、螺二克芬(spirodiclofen)、螺甲蟎酯(spiromesifen、BSN 2060)、硫丙磷(sulprofos)、得布芬載(tebufenozide)、得福隆(teflubenzuron)、七氟菊酯(tefluthrin)、託福松(terbufos)、殺蟲畏(tetrachlorvinphos)、噻蟲啉(thiacloprid)、噻蟲嗪(thiamethoxam)、硫雙威(thiodicarb)、硫殺太鈉(thiosultap-sodium)、唑蟲醯胺(tolfenpyrad)、泰滅寧(tralomethrin)、唑蚜威(triazamate)、三氯磷酸酯(trichlorfon)、殺蟲隆(triflumuron)、得滅克(aldicarb)、芬滅松(fenamiphos)、三亞蟎(amitraz)、滅蟎猛(chinomethionat)、殺蟎酯(chlorobenzilate)、環己錫(cyhexatin)、開樂散(dicofol)、得氯蟎(dienochlor)、伊妥咢坐(etoxazole)、芬那劄奎(fenazaquin)、芬布賜(fenbutatin oxide)、芬普蟎(fenpyroximate)、合賽多(hexythiazox)、克蟎特(propargite)、噠蟎靈(pyridaben)、吡蟎胺(tebufenpyrad)、蘇力菌亞莎華(aizawai )亞種、蘇力菌卻氏卡奇(kurstaki )亞種、蘇力菌δ內毒素、桿狀病毒、昆蟲致病細菌、昆蟲致病病毒及昆蟲致病真菌。The composition of claim 11, wherein the at least one additional biologically active compound or agent is selected from the group consisting of abamectin, acephate, acetamiprid, acetamidine Acetoprole, amidoflumet (S-1955), avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifen (bifenazate), bistrifluron, buprofezin, carbofuran, cartap, chlorfenapyr, chlorfluazuron, tausson ( Chlorpyrifos), methyl tausson, chromafenozide, clothianidin, cyfluthrin, beta-cyfluthrin, cyhalothrin, λ-race Lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dieldrin , diflubenzuron, dimethoate, dinotefuran, difino Lan), emamectin, endosulfan, esfenvalerate, ethiprole, fenothiocarb, fenoxycarb, fenpropathrin ), fenvalerate, fipronil, flonicamid, flubendiamide, flucythrinate, tau-fluvalinate, Flufenerim (UR-50701), flufenoxuron, gamma-cyhalothrin, halofenozide, hexaflumuron, hydramethylnon, Imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaflumizone, polyacetaldehyde ), methamidophos, methidathion, methomyl, metheprene, methoxychlor, methoxyfenozide, trimethoprim (metofluthrin), monocrotophos, methoxyfenozide, nitenpyram, niesin (nit Hiazine), novaluron, novolonuron (XDE-007), oxamyl, parathion, parathion-methyl, permethrin ), phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin ), protrifenbute, pymetrozine, pyrethrin, pyridalyl, pyriproxyfen, rotenone, lanidine ( Ryanodine), S1812 (Valent), spinosad, spirodiclofen, spiromesifen (BSN 2060), sulprofos, tebufenozide, Teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiophene Thiosultap-sodium, tolfenpyrad, tralmethrin, triazamate, trichlor Fon), triflumuron, aldicarb, fenamiphos, amitraz, chinomethionat, chlorobenzilate, cyhexatin , dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpyroximate, cycad ( Hexythiazox), propargite, pyridaben, tebufenpyrad, azawai subspecies, sulphide kurstaki subspecies, su δ endotoxin, baculovirus, insect pathogenic bacteria, insect pathogenic viruses and insect pathogenic fungi. 如請求項12之組合物，其中該至少一額外生物活性化合物或藥劑係選自由以下物質組成之群：賽滅甯、賽洛寧、賽扶寧及β-賽扶寧、益化利、芬化利、泰滅寧、苯硫威、滅多蟲、歐殺滅、硫雙威、亞滅培、可尼丁、益達胺、噻蟲嗪、噻蟲啉、茚蟲威、賜諾殺、阿巴汀、阿維菌素、 伊曼美丁、安殺番、伊希普、費普尼、氟芬隆、殺蟲隆、戴芬蘭、比普西芬、吡蚜酮、三亞蟎、蘇力菌亞莎華亞種、蘇力菌卻氏卡奇亞種、蘇力菌δ內毒素及昆蟲致病真菌。 The composition of claim 12, wherein the at least one additional biologically active compound or agent is selected from the group consisting of Sai-Ning, Xelonine, Sai-Fanning, and β-赛福宁, Yihua Li, Fen Huali, Taining, phenylthiocarb, chlorpyrifos, chlorpyrifos, thiodicarb, arsenic, cotinine, edetamine, thiamethoxam, thiacloprid, indoxacarb, chlorhexidine, Abatatin, avermectin, Imanmeiding, Anzufen, Ishipu, Fapreni, Flufenolone, Insecticidal, Daifon, Pipoxifene, Pyridoxine, Sanya, Sulawia, Yashahua, Su Bacillus subtilis, serotonin delta endotoxin and insect pathogenic fungi. 如請求項10之組合物，其係呈土壤浸潤液體調配物形式。 The composition of claim 10 which is in the form of a soil infiltrating liquid formulation. 一種用於控制一無脊椎害蟲之噴霧組合物，其包含：(a)生物有效量的如請求項1之化合物或如請求項10之組合物；及(b)推進劑。 A spray composition for controlling an invertebrate pest comprising: (a) a biologically effective amount of a compound of claim 1 or a composition of claim 10; and (b) a propellant. 一種用於控制一無脊椎害蟲之誘餌組合物，其包含：(a)生物有效量的如請求項1之化合物或如請求項10之組合物；及(b)一或多種食物材料；(c)視情況之引誘劑；及(d)視情況之保濕劑。 A bait composition for controlling an invertebrate pest comprising: (a) a biologically effective amount of a compound of claim 1 or a composition of claim 10; and (b) one or more food materials; ) an attractant as appropriate; and (d) a moisturizer as appropriate. 一種用於控制一無脊椎害蟲之捕獲裝置，其包含：(a)如請求項16之誘餌組合物；及(b)適合容納該誘餌組合物之一外殼，其中該外殼具有至少一開口，其尺寸允許該無脊椎害蟲穿過該開口而使該無脊椎害蟲可自該外殼外之位置得以接近該誘餌組合物，且其中該外殼另外適合置放於或靠近該無脊椎害蟲之潛在或已知活躍地點。 A capture device for controlling an invertebrate pest, comprising: (a) the bait composition of claim 16; and (b) an outer casing adapted to receive the bait composition, wherein the outer casing has at least one opening Dimensions allow the invertebrate pest to pass through the opening such that the invertebrate pest can access the bait composition from a location outside the outer casing, and wherein the outer casing is otherwise adapted to be placed in or near the potential or known of the invertebrate pest Active location. 一種用於控制一無脊椎害蟲之方法，其包含使該無脊椎害蟲或其環境與生物有效量的如請求項1之化合物接觸。 A method for controlling an invertebrate pest comprising contacting the invertebrate pest or an environment thereof with a biologically effective amount of a compound of claim 1. 一種用於控制一無脊椎害蟲之方法，其包含使該無脊椎害蟲或其環境與如請求項10之組合物接觸。 A method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a composition as claimed in claim 10. 如請求項19之方法，其中該環境為土壤且該組合物係以土壤浸潤調配物形式施用至該土壤上。 The method of claim 19, wherein the environment is soil and the composition is applied to the soil in the form of a soil infiltration formulation. 一種用於控制蟑螂、螞蟻或白蟻之方法，其包含使蟑螂、螞蟻或白蟻與如請求項17之捕獲裝置中的該誘餌組合物接觸。 A method for controlling cockroaches, ants or termites comprising contacting a cockroach, ant or termite with the bait composition as in the capture device of claim 17. 一種用於控制蚊子、黑蠅、螯蠅、鹿蠅、馬蜂、黃蜂、胡蜂、大黃蜂、壁虱、蜘蛛、螞蟻或蠓蟲之方法，其包含使蚊子、黑蠅、螯蠅、鹿蠅、馬蜂、黃蜂、胡蜂、大黃蜂、壁虱、蜘蛛、螞蟻或蠓蟲與自一噴霧容器中分配之如請求項15之噴霧組合物接觸。 A method for controlling mosquitoes, black flies, larvae, deer flies, wasps, wasps, wasps, bumblebees, ticks, spiders, ants or mites, which comprises making mosquitoes, black flies, larvae, deer flies, The wasp, wasp, wasp, bumblebee, ticks, spiders, ants or mites are in contact with the spray composition of claim 15 dispensed from a spray container. 一種式10 之化合物或其鹽， 其中：R1a 為C1 -C6 烷基、C2 -C6 烯基、C2 -C6 炔基、C3 -C6 環烷基、C1 -C6 鹵烷基、C2 -C6 鹵烯基、C2 -C6 鹵炔基、C3 -C6 鹵環烷基、鹵素、CN、CHO、NO2 、C1 -C4 烷氧基、C1 -C4 鹵烷氧基、C1 -C4 烷基硫基、C1 -C4 烷基亞磺醯基、C1 -C4 烷基磺醯基、C1 -C4 鹵烷基硫基、C1 -C4 鹵烷基亞磺醯 基、C1 -C4 鹵烷基磺醯基、C2 -C4 烷基羰基、C2 -C4 烷氧基羰基、C2 -C4 烷基胺基羰基、C3 -C5 二烷基胺基羰基、C1 -C4 烷基胺基或C2 -C6 二烷基胺基；R1b 為H、C1 -C6 烷基、C2 -C6 烯基、C2 -C6 炔基、C3 -C6 環烷基、C1 -C6 鹵烷基、C2 -C6 鹵烯基、C2 -C6 鹵炔基、C3 -C6 鹵環烷基、鹵素、CN、CHO、NO2 、C1 -C4 烷氧基、C1 -C4 鹵烷氧基、C1 -C4 烷基硫基、C1 -C4 烷基亞磺醯基、C1 -C4 烷基磺醯基、C1 -C4 鹵烷基硫基、C1 -C4 鹵烷基亞磺醯基、C1 -C4 鹵烷基磺醯基、C2 -C4 烷基羰基、C2 -C4 烷氧基羰基、C2 -C4 烷基胺基羰基、C3 -C5 二烷基胺基羰基、C1 -C4 烷基胺基或C2 -C6 二烷基胺基；R2 為H；或C1 -C6 烷基、C2 -C6 烯基、C2 -C6 炔基或C3 -C6 環烷基，各視情況經一或多個選自由鹵素、CN、NO2 、羥基、C1 -C4 烷基、C1 -C4 烷氧基、C1 -C4 烷基硫基、C1 -C4 烷基亞磺醯基、C1 -C4 烷基磺醯基、C2 -C4 烷氧基羰基、C1 -C4 烷基胺基、C2 -C8 二烷基胺基及C3 -C6 環烷基胺基組成之群之取代基取代；或R2 為C2 -C6 烷基羰基、C2 -C6 烷氧基羰基、C2 -C6 烷基胺基羰基或C3 -C8 二烷基胺基羰基；R3 為H、C1 -C6 烷基、C2 -C6 烯基、C2 -C6 炔基、C3 -C6 環烷基、C1 -C4 烷氧基、C1 -C4 烷基胺基、C2 -C8 二烷基胺基、C3 -C6 環烷基胺基、C2 -C6 烷氧基羰基或C2 -C6 烷基羰基；且R4 為C5 -C12 烯基環烷基、C5 -C12 炔基環烷基、C4 -C12 環烷 基烷基、C5 -C12 環烷基烯基、C5 -C12 環烷基炔基、C4 -C12 環烯基烷基或C4 -C12 烷基環烯基，各視情況經1至6個選自CH3 及鹵素之取代基取代；或R4 為C3 -C5 環氧乙烷基烷基、C3 -C5 硫雜環丙烷基烷基、C4 -C6 環氧丙烷基烷基、C4 -C6 硫雜環丁烷基烷基、3-環氧丙烷基或3-硫雜環丁烷基，各視情況經1至5個獨立選自C1 -C3 烷基、C1 -C3 鹵烷基、鹵素、CN、C2 -C4 烷氧基羰基及C2 -C4 鹵烷氧基羰基之取代基取代；或R4 為C3 -C5 吖丙啶基烷基、C4 -C6 吖丁啶基烷基或3-吖丁啶基，其經連接至氮原子R10 取代，且視情況在碳原子上經1至5個獨立選自C1 -C3 烷基、C1 -C3 鹵烷基、鹵素、CN、C2 -C4 烷氧基羰基及C2 -C4 鹵烷氧基羰基之取代基取代。a compound of the formula 10 or a salt thereof, Wherein: R 1a is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 - C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, CN, CHO, NO 2 , C 1 -C 4 alkoxy, C 1 -C 4 halo Oxyl, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 - C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkoxycarbonyl, C 2 -C 4 alkylamino Carbonyl, C 3 -C 5 dialkylaminocarbonyl, C 1 -C 4 alkylamino or C 2 -C 6 dialkylamino; R 1b is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, CN, CHO, NO 2 , C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 Haloalkylsulfonyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkane Oxycarbonyl, C 2 -C 4 alkylaminocarbonyl, C 3 -C 5 dialkylaminocarbonyl, C 1 -C 4 alkylamino or C 2 -C 6 dialkylamino; R 2 Is H; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl, each optionally selected from halogen, CN by one or more , NO 2 , hydroxy, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 a group consisting of an alkylsulfonyl group, a C 2 -C 4 alkoxycarbonyl group, a C 1 -C 4 alkylamino group, a C 2 -C 8 dialkylamino group, and a C 3 -C 6 cycloalkylamine group Substituted by a substituent; or R 2 is C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl or C 3 -C 8 dialkylaminocarbonyl ; R 3 is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 1 a -C 4 alkylamino group, a C 2 -C 8 dialkylamino group, a C 3 -C 6 cycloalkylamino group, a C 2 -C 6 alkoxycarbonyl group or a C 2 -C 6 alkylcarbonyl group; R 4 is C 5 -C 12 alkenylcycloalkyl, C 5 -C 12 alkynylcycloalkyl, C 4 -C 12 cycloalkylalkyl, C 5 -C 12 cycloalkylalkenyl, C 5 - C 12 cycloalkyl Alkynyl group, C 4 -C 12 cycloalkenylalkyl or C 4 -C 12 cycloalkenyl group, each optionally substituted with 1-6 halogen selected from CH 3 and the substituents; R 4 is C 3 or -C 5 oxiranylalkyl, C 3 -C 5 thicyclopropylalkyl, C 4 -C 6 epoxypropanealkyl, C 4 -C 6 thietanealkyl, 3-epoxypropane or 3-thietyl, each optionally 1 to 5 independently selected from C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, halogen, CN, C 2 Substituted with a substituent of -C 4 alkoxycarbonyl and C 2 -C 4 haloalkoxycarbonyl; or R 4 is C 3 -C 5 aziridinylalkyl, C 4 -C 6 azetidinylalkyl or 3 Azetidinyl, which is substituted by a nitrogen atom R 10 and, as the case may be, 1 to 5 independently selected from C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, halogen, CN, on a carbon atom Substituted with a C 2 -C 4 alkoxycarbonyl group and a C 2 -C 4 haloalkoxycarbonyl group. 如請求項23之化合物，其中：R1a 為C1 -C4 烷基、C1 -C4 鹵烷基、鹵素、CN、NO2 、C1 -C4 烷氧基、C1 -C4 鹵烷氧基、C1 -C4 烷基硫基、C1 -C4 烷基亞磺醯基、C1 -C4 烷基磺醯基、C1 -C4 鹵烷基硫基、C1 -C4 鹵烷基亞磺醯基或C1 -C4 鹵烷基磺醯基；R1b 為H、C1 -C4 烷基、C1 -C4 鹵烷基、鹵素、CN、NO2 、C1 -C4 烷氧基、C1 -C4 鹵烷氧基、C1 -C4 烷基硫基、C1 -C4 烷基亞磺醯基、C1 -C4 烷基磺醯基、C1 -C4 鹵烷基硫基、C1 -C4 鹵烷基亞磺醯基或C1 -C4 鹵烷基磺醯基；R2 及R3 各自獨立為H、C1 -C4 烷基、C2 -C4 烯基、C2 -C4 炔基、C3 -C6 環烷基、C2 -C6 烷基羰基或C2 -C6 烷氧基羰基；且 R4 為(C3 -C4 )環烷基(C1 -C8 )烷基，各視情況經1至6個選自CH3 及鹵素之取代基取代；或R4 為C3 -C5 環氧乙烷基烷基、C4 -C6 環氧丙烷基烷基或3-環氧丙烷基，各視情況經1至2個獨立選自CH3 、CF3 、鹵素、CN及C(O)OCH3 之取代基取代。The compound of claim 23, wherein: R 1a is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halogen, CN, NO 2 , C 1 -C 4 alkoxy, C 1 -C 4 Haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl or C 1 -C 4 haloalkylsulfonyl; R 1b is H, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halogen, CN, NO 2 , C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkane Sulfosyl, C 1 -C 4 haloalkylthio, C 1 -C 4 haloalkylsulfinyl or C 1 -C 4 haloalkylsulfonyl; R 2 and R 3 are each independently H , C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkylcarbonyl or C 2 -C 6 alkoxy a carbonyl group; and R 4 is a (C 3 -C 4 )cycloalkyl(C 1 -C 8 )alkyl group, each optionally substituted with 1 to 6 substituents selected from CH 3 and halogen; or R 4 is C 3 -C 5 oxiranylalkyl, C 4 -C 6 propylene oxide alkyl or 3-epoxypropane, each optionally 1 to 2 independently selected from CH 3 , CF 3 , halogen Substituting substituents for CN and C(O)OCH 3 . 如請求項24之化合物，其中：R1a 為CH3 、CF3 、OCF3 、OCHF2 、S(O)n CF3 、S(O)n CHF2 、CN或鹵素；R1b 為H、CH3 、CF3 、OCF3 、OCHF2 、S(O)p CF3 、S(O)p CHF2 、CN或鹵素；R2 及R3 為H；n為0、1或2；且p為0、1或2。The compound of claim 24, wherein: R 1a is CH 3 , CF 3 , OCF 3 , OCHF 2 , S(O) n CF 3 , S(O) n CHF 2 , CN or halogen; R 1b is H, CH 3 , CF 3 , OCF 3 , OCHF 2 , S(O) p CF 3 , S(O) p CHF 2 , CN or halogen; R 2 and R 3 are H; n is 0, 1 or 2; and p is 0, 1 or 2. 一種化合物，其為2-胺基-5-氯-N -(環丙基甲基)-3-甲基苯甲醯胺。A compound which is 2-amino-5-chloro- N- (cyclopropylmethyl)-3-methylbenzamide. 一種化合物，其為2-胺基-5-溴-N -(環丙基甲基)-3-甲基苯甲醯胺。A compound which is 2-amino-5-bromo- N- (cyclopropylmethyl)-3-methylbenzamide. 一種化合物，其為2-胺基-3,5-二氯-N -(環丙基甲基)-苯甲醯胺。A compound which is 2-amino-3,5-dichloro- N- (cyclopropylmethyl)-benzamide. 一種化合物，其為2-胺基-3,5-二溴-N -(環丙基甲基)-苯甲醯胺。A compound which is 2-amino-3,5-dibromo- N- (cyclopropylmethyl)-benzamide. 一種化合物，其為2-胺基-5-氯-N -(環丙基乙基)-3-甲基苯甲醯胺。A compound which is 2-amino-5-chloro- N- (cyclopropylethyl)-3-methylbenzamide. 一種化合物，其為2-胺基-5-溴-N -(1-環丙基乙基)-3-甲基苯甲醯胺。A compound which is 2-amino-5-bromo- N- (1-cyclopropylethyl)-3-methylbenzamide. 一種化合物，其為2-胺基-3,5-二氯-N -(1-環丙基乙基)- 苯甲醯胺。A compound which is 2-amino-3,5-dichloro- N- (1-cyclopropylethyl)-benzamide. 一種化合物，其為2-胺基-3,5-二溴-N -(1-環丙基乙基)-苯甲醯胺。A compound which is 2-amino-3,5-dibromo- N- (1-cyclopropylethyl)-benzamide.
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WO2001070671A2 (en) * 2000-03-22 2001-09-27 E.I. Du Pont De Nemours And Company Insecticidal anthranilamides
WO2003015518A1 (en) * 2001-08-13 2003-02-27 E.I. Du Pont De Nemours And Company Method for controlling particular insect pests by applying anthranilamide compounds

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001070671A2 (en) * 2000-03-22 2001-09-27 E.I. Du Pont De Nemours And Company Insecticidal anthranilamides
WO2003015518A1 (en) * 2001-08-13 2003-02-27 E.I. Du Pont De Nemours And Company Method for controlling particular insect pests by applying anthranilamide compounds

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