TW201348207A - 含新穎亞胺吡啶衍生物之有害生物防治用組成物 - Google Patents
含新穎亞胺吡啶衍生物之有害生物防治用組成物 Download PDFInfo
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- TW201348207A TW201348207A TW102106998A TW102106998A TW201348207A TW 201348207 A TW201348207 A TW 201348207A TW 102106998 A TW102106998 A TW 102106998A TW 102106998 A TW102106998 A TW 102106998A TW 201348207 A TW201348207 A TW 201348207A
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- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 91
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
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- 239000004480 active ingredient Substances 0.000 claims description 23
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 22
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- HOKKPVIRMVDYPB-UVTDQMKNSA-N (Z)-thiacloprid Chemical compound C1=NC(Cl)=CC=C1CN1C(=N/C#N)/SCC1 HOKKPVIRMVDYPB-UVTDQMKNSA-N 0.000 claims description 8
- AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 claims description 8
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 claims description 8
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- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 claims description 8
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- YXWCBRDRVXHABN-JCMHNJIXSA-N [cyano-(4-fluoro-3-phenoxyphenyl)methyl] 3-[(z)-2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropane-1-carboxylate Chemical compound C=1C=C(F)C(OC=2C=CC=CC=2)=CC=1C(C#N)OC(=O)C1C(C)(C)C1\C=C(/Cl)C1=CC=C(Cl)C=C1 YXWCBRDRVXHABN-JCMHNJIXSA-N 0.000 claims description 6
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/14—Ethers
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
-
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- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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Abstract
本發明係提供一種含有下述式(I)所示之亞胺基吡啶衍生物與其他有害生物防治劑之至少1種所成之有害生物防治用組成物,□〔式中,Ar表示可經取代的5-6員之雜環、A表示含1個以上氮原子之5-10員具不飽和鍵結的雜環,且存在環上之氮原子的鄰接位上具有被R基所取代之亞胺基、Y表示氫、鹵素等、R表示下述之式(a)~(e)、(y)及(z)所示之基的任一者□
Description
本發明係關於含有新穎亞胺基吡啶衍生物與其他有害生物防治劑之至少1種所成的有害生物防治用組成物。
至今為止,雖以發現多數的有害生物防治劑,但從藥劑感受性降低的問題、效果持續性的課題、作業者的安全性或在環境影響面的安全性等來看,至今仍需要更具高安全性的新穎藥劑。再者,農業中,為求病害蟲防治作業的省力化,一般乃混合有害生物防治用藥劑之複數成分,處理於種子或育苗期的作物,如此情況下,具有浸透移行性的長期殘效型藥劑之使用備受期望。又,藉由種子處理或育苗期處理,亦可解決對農地以外之周邊環境的藥劑飛散、防治者的被曝等。
專利文獻1中雖揭示具有與式(I)所示之化合物同樣環構造的複數化合物,但該用途為除草劑,並未記載有關有害生物之防治。
專利文獻2中,雖揭示有N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙醯胺之構
造式(專利文獻2之第1表化合物編號3),但其製造方法並無任何的揭示,且並未包含於被認定具有害生物防治活性之化合物群的表列中(專利文獻2之第2表、第3表)。
專利文獻3中,雖揭示有N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙醯胺之構造式(專利文獻3之表7的實施例編號12),但其製造方法並無任何的揭示,實施例中並未舉出具有害生物防治活性的化合物之例。
非專利文獻1中,雖揭示有具與後述式(I)所示之化合物類似之環構造的複數化合物,但只不過揭示了合成中間體。
專利文獻4中,雖揭示了具有與式(I)所示之化合物類似的環構造之複數的化合物,但有關具有三氟醋酸亞胺基構造之化合物,並沒有任何的揭示或教示。
再者,此等文獻中,有關混合本發明之新穎亞胺基吡啶衍生物與其他有害生物防治劑混合時的有害生物防治活性,並無任何的記載。
〔專利文獻1〕歐洲公開公報432600號
〔專利文獻2〕特開平5-78323
〔專利文獻3〕歐洲公開公報268915號
〔專利文獻4〕歐洲公開公報259738號
〔非專利文獻1〕Chemische Berichte (1955)、88, 1103-8
本發明的課題在於,藉由提供一種新穎的有害生物防治劑,而得以解決有害生物防治區域中,藥劑感受性的降低、效果的持續性、使用時的安全性等之既存藥劑所具有的問題。
為解決上述課題而專致於一再檢討的結果,本發明者們發現,式(I)所示之新穎亞胺基吡啶衍生物對有害生物具有優異的防治效果,進而發現,藉由含有此等新穎亞胺基吡啶衍生物與其他有害生物防治劑的至少1種,可顯示出較單劑使用更為優異之防治效果的組成物及其使用方法。本發明乃基於此見解所完成者。
因此,本發明之目的在於提供一種有害生物防治用組成物,其係含有下述之式(I)所示之新穎亞胺基吡啶衍生物、或該等之酸加成鹽的至少1種與其他有害生物防治劑的至少1種所成,其係對廣泛的有害生物而言,係可以低藥量即顯示出優異的防治效果之有害生物防治用組成物。
(1)提供一種有害生物防治用組成物,其係含有作為有效成分之次式(I)所示之新穎亞胺基吡啶衍生物、或該等之酸加成鹽的至少1種與其他有害生物防治劑的至少1種而成者,
〔式中,Ar表示可經取代之苯基、可經取代之5~6員之雜環、或4~10員之雜環烷基、A表示具有含1個以上氮原子的5~10員不飽和鍵結之雜環,且存在環上之氮原子的鄰接位上具有被R基所取代之亞胺基、Y表示氫原子、鹵素原子、羥基、可經鹵素原子取代之C1~C6烷基、可經鹵素原子取代之C1~C6烷基氧基、氰基或硝基、R表示下述之式(a)~(e)、(y)及(z)所示之基的任一者、
在此,R1表示氫原子、已經取代之C1~C6烷基、可經鹵素原子取代之C2~C6烯基、可經鹵素原子取代之C2~C6炔基、五氟苯基、R2表示已經鹵素原子取代之C1~C6烷基、無取代C3~C6分支或環狀烷基、可經鹵素原子取代之C2~C6烯基、可經鹵素原子取代之C2~C6炔基、取代或無取代之(C6~C10)芳基、取代或無取代5~10員雜環、取代或無取代之苯甲基、R3表示可經鹵素原子取代之C1~C6烷基、可經鹵素原子取代之C2~C6烯基、可經鹵素原子取代之C2~C6炔基、取代或無取代之(C6~C10)芳基、取代或無取代之(C6~C10)芳基(C1~C6)烷基、取代或無取代之(C6~C10)芳基(C2~C6)烯基、取代或無取代之(C6~C10)芳基(C2~C6)炔基、取代或無取代之苯氧基(C1~C6)烷基、取代或無取代之苯氧基(C2~C6)烯基、取代或無取代之苯氧基(C2~C6)炔基、取代或無取代之5~10員雜環、取代或無取代之5~10員雜環(C1~C6)烷基、取代或無取代之5~10員雜環(C2~C6)烯基、取代或無取代之5~10員雜環(C2~C6)炔基、(C1~C4)烷氧基(C1~C5)烷基、(C1~C4)烷氧基(C2~C5)烯基、(C1~C4)烷氧基(C2~C5)炔基、(C1~C4)烷硫基(C1~C5)烷基、(C1~C4)烷硫基(C2~C5)烯基、(C1~C4)烷硫基(C2~C5)炔基、R4表示氫原子、甲醯基、可經取代之C1~C18烷
基、可經鹵素原子取代之C2~C6烯基、可經鹵素原子取代之C2~C6炔基、取代或無取代之(C6~C10)芳基、取代或無取代之(C6~C10)芳基(C1~C6)烷基、取代或無取代之(C6~C10)芳基(C2~C6)烯基、取代或無取代之(C6~C10)芳基(C2~C6)炔基、取代或無取代之苯氧基(C1~C6)烷基、取代或無取代之苯氧基(C2~C6)烯基、取代或無取代之苯氧基(C2~C6)炔基、取代或無取代之5~10員雜環、取代或無取代之5~10員雜環(C1~C6)烷基、取代或無取代之5~10員雜環(C2~C6)烯基、取代或無取代之5~10員雜環(C2~C6)炔基、(C1~C4)烷氧基(C1~C5)烷基、(C1~C4)烷氧基(C2~C5)烯基、(C1~C4)烷氧基(C2~C5)炔基、(C1~C4)烷硫基(C1~C5)烷基、(C1~C4)烷硫基(C2~C5)烯基、(C1~C4)烷硫基(C2~C5)炔基、及下述之式(f)~(n)所示之基的任一者、
在此,R4a、R4b、R4c表示可經鹵素原子取代之C1~C6烷基、可經鹵素原子取代之C2~C6烯基、可經鹵素
原子取代之C2~C6炔基、取代或無取代之(C6~C10)芳基、取代或無取代之(C6~C10)芳基(C1~C6)烷基、取代或無取代之(C6~C10)芳基(C2~C6)烯基、取代或無取代之(C6~C10)芳基(C2~C6)炔基、取代或無取代之苯氧基(C1~C6)烷基、取代或無取代之苯氧基(C2~C6)烯基、取代或無取代之苯氧基(C2~C6)炔基、取代或無取代之5~10員雜環、取代或無取代之5~10員雜環(C1~C6)烷基、取代或無取代之5~10員雜環(C2~C6)烯基、取代或無取代之5~10員雜環(C2~C6)炔基、(C1~C4)烷氧基(C1~C5)烷基、(C1~C4)烷氧基(C2~C5)烯基、(C1~C4)烷氧基(C2~C5)炔基、(C1~C4)烷硫基(C1~C5)烷基、(C1~C4)烷硫基(C2~C5)烯基、(C1~C4)烷硫基(C2~C5)炔基、R4d表示可經鹵素原子取代之C1~C6烷基、可經鹵素原子取代之C2~C6烯基、可經鹵素原子取代之C2~C6炔基、取代或無取代之(C6~C10)芳基、取代或無取代之5~10員雜環、R4e、R4f互相獨立地表示氫原子、可經鹵素原子取代之C1~C6烷基、可經鹵素原子取代之C2~C6烯基、可經鹵素原子取代之C2~C6炔基、取代或無取代之(C6~C10)芳基、取代或無取代之5~10員雜環)、R5表示可經鹵素原子取代之C1~C6烷基、可經鹵素原子取代之C2~C6烯基、可經鹵素原子取代之C2~C6
炔基、取代或無取代之(C6~C10)芳基、取代或無取代之(C6~C10)芳基(C1~C6)烷基、取代或無取代之(C6~C10)芳基(C2~C6)烯基、取代或無取代之(C6~C10)芳基(C2~C6)炔基、取代或無取代之苯氧基(C1~C6)烷基、取代或無取代之苯氧基(C2~C6)烯基、取代或無取代之苯氧基(C2~C6)炔基、取代或無取代之5~10員雜環、取代或無取代之5~10員雜環(C1~C6)烷基、取代或無取代之5~10員雜環(C2~C6)烯基、取代或無取代之5~10員雜環(C2~C6)炔基、(C1~C4)烷氧基(C1~C5)烷基、(C1~C4)烷氧基(C2~C5)烯基、(C1~C4)烷氧基(C2~C5)炔基、(C1~C4)烷硫基(C1~C5)烷基、(C1~C4)烷硫基(C2~C5)烯基、(C1~C4)烷硫基(C2~C5)炔基、R6表示氫原子、甲醯基、O,O’-C1~C4烷基磷氧基、可經取代之C1~C18烷基、可經鹵素原子取代之C2~C6烯基、可經鹵素原子取代之C2~C6炔基、取代或無取代之(C6~C10)芳基、取代或無取代之(C6~C10)芳基(C1~C6)烷基、取代或無取代之(C6~C10)芳基(C2~C6)烯基、取代或無取代之(C6~C10)芳基(C2~C6)炔基、取代或無取代之苯氧基(C1~C6)烷基、取代或無取代之苯氧基(C2~C6)烯基、取代或無取代之苯氧基(C2~C6)炔基、取代或無取代之5~10員雜環、取代或無取代之5~10員雜環(C1~C6)烷基、取代或無取代之5~10員雜環(C2~C6)烯基、取代或無
取代之5~10員雜環(C2~C6)炔基、(C1~C4)烷氧基(C1~C5)烷基、(C1~C4)烷氧基(C2~C5)烯基、(C1~C4)烷氧基(C2~C5)炔基、(C1~C4)烷硫基(C1~C5)烷基、(C1~C4)烷硫基(C2~C5)烯基、(C1~C4)烷硫基(C2~C5)炔基、及下述之式(o)~(x)所示之基的任一者、
在此,R6a、R6b、R6c表示可經鹵素原子取代之C1~C6烷基、可經鹵素原子取代之C2~C6烯基、可經鹵素原子取代之C2~C6炔基、取代或無取代之(C6~C10)芳基、取代或無取代之(C6~C10)芳基(C1~C6)烷基、取代或無取代之(C6~C10)芳基(C2~C6)烯基、取代或無取代之(C6~C10)芳基(C2~C6)炔基、取代或無取代之苯氧基(C1~C6)烷基、取代或無取代之苯氧基(C2~C6)烯基、取代或無取代之苯氧基(C2~C6)炔基、取代或無取代之5~10員雜環、取代或無取代之5~10員雜環(C1~C6)烷基、取代或無取代之5~10員雜環(C2~C6)烯基、取代或無取代之5~10員雜環
(C2~C6)炔基、(C1~C4)烷氧基(C1~C5)烷基、(C1~C4)烷氧基(C2~C5)烯基、(C1~C4)烷氧基(C2~C5)炔基、(C1~C4)烷硫基(C1~C5)烷基、(C1~C4)烷硫基(C2~C5)烯基、(C1~C4)烷硫基(C2~C5)炔基、R6d表示可經鹵素原子取代之C1~C6烷基、可藉由鹵素原子所經取代的C2~C6烯基、可經鹵素原子取代之C2~C6炔基、取代或無取代之(C6~C10)芳基、取代或無取代之5~10員雜環、R6e、R6f互相獨立地表示氫原子、可經鹵素原子取代之C1~C6烷基、可經鹵素原子取代之C2~C6烯基、可經鹵素原子取代之C2~C6炔基、(C1~C4)烷氧基(C1~C5)烷基、(C1~C4)烷硫基(C1~C5)烷基、取代或無取代之(C6~C10)芳基、取代或無取代之(C6~C10)芳基(C1~C6)烷基、取代或無取代之5~10員雜環、R6g、R6h互相獨立地表示氫原子、可經鹵素原子取代之C1~C6烷基、可經鹵素原子取代之C2~C6烯基、可經鹵素原子取代之C2~C6炔基、取代或無取代之(C6~C10)芳基、取代或無取代之5~10員雜環、R6i、R6j、R6k互相獨立地表示氫原子、可經鹵素原子取代之C1~C6烷基、可經鹵素原子取代之C2~C6烯基、可經鹵素原子取代之C2~C6炔基、取代或無取代之(C6~C10)芳基)、
R7表示可經鹵素原子取代之C1~C6烷基、可經鹵素原子取代之C1~C6烯基、可經鹵素原子取代之C2~C6炔基、取代或無取代之(C6~C10)芳基、取代或無取代之(C6~C10)芳基(C1~C6)烷基、取代或無取代之(C6~C10)芳基(C2~C6)烯基、取代或無取代之(C6~C10)芳基(C2~C6)炔基、取代或無取代之苯氧基(C1~C6)烷基、取代或無取代之苯氧基(C2~C6)烯基、取代或無取代之苯氧基(C2~C6)炔基、取代或無取代之5~10員雜環、取代或無取代之5~10員雜環(C1~C6)烷基、取代或無取代之5~10員雜環(C2~C6)烯基、取代或無取代之5~10員雜環(C2~C6)炔基、(C1~C4)烷氧基(C1~C5)烷基、(C1~C4)烷氧基(C2~C5)烯基、(C1~C4)烷氧基(C2~C5)炔基、(C1~C4)烷硫基(C1~C5)烷基、(C1~C4)烷硫基(C2~C5)烯基、(C1~C4)烷硫基(C2~C5)炔基、Y1及Y2可互為相同或相異,表示氧原子或硫原子、Ry表示可經鹵素原子取代之C1~C6烷基、可經鹵素原子取代之C2~C6烯基、可經鹵素原子取代之C2~C6炔基、取代或無取代之(C6~C10)芳基、取代或無取代之(C6~C10)芳基(C1~C6)烷基、取代或無取代之(C6~C10)芳基(C2~C6)烯基、取代或無取代之(C6~C10)芳基(C2~C6)炔基、取代或無取代之苯氧基(C1~C6)烷基、取代或無取代之苯氧基(C2~C6)烯基、取代或無取代之苯氧基(C2~C6)炔基、取代或無取代
之5~10員雜環、取代或無取代之5~10員雜環(C1~C6)烷基、取代或無取代之5~10員雜環(C2~C6)烯基、取代或無取代之5~10員雜環(C2~C6)炔基、Rz表示可經鹵素原子取代之C1~C6烷基、可經鹵素原子取代之C2~C6烯基、可經鹵素原子取代之C2~C6炔基、取代或無取代之(C6~C10)芳基、取代或無取代之(C6~C10)芳基(C1~C6)烷基、取代或無取代之(C6~C10)芳基(C2~C6)烯基、取代或無取代之(C6~C10)芳基(C2~C6)炔基、取代或無取代之苯氧基(C1~C6)烷基、取代或無取代之苯氧基(C2~C6)烯基、取代或無取代之苯氧基(C2~C6)炔基、取代或無取代之5~10員雜環、取代或無取代之5~10員雜環(C1~C6)烷基、取代或無取代之5~10員雜環(C2~C6)烯基、取代或無取代之5~10員雜環(C2~C6)炔基、(C1~C4)烷氧基(C1~C5)烷基、(C1~C4)烷氧基(C2~C5)烯基、(C1~C4)烷氧基(C2~C5)炔基、(C1~C4)烷硫基(C1~C5)烷基、(C1~C4)烷硫基(C2~C5)烯基、(C1~C4)烷硫基(C2~C5)炔基、n表示1或2〕。
(2)提供一種有害生物防治用組成物,其係含有作為有效成分之次式(Ia)所示之胺衍生物、或該等之酸加成鹽的至少1種與其他有害生物防治劑的至少1種所成。
〔在此,Ar表示可以鹵素原子、羥基、可經鹵素原子取代之C1~C6烷基、可經鹵素原子取代之C1~C6烷基氧基、氰基或硝基所取代之吡啶基、或可以鹵素原子、可經鹵素原子取代之C1~C4烷基、可經鹵素原子取代之烷基氧基、羥基、氰基或硝基所取代之嘧啶基、Y表示氫原子、鹵素原子、羥基、可經鹵素原子取代之C1~C6烷基、可經鹵素原子取代之C1~C6烷基氧基、氰基或硝基、R1表示已經鹵素取代之C1~C6烷基。〕
(3)提供如(1)中記載之有害生物防治用組成物,其中,Ar係6-氯-3-吡啶基、6-氯-5-氟-3-吡啶基、6-氟-3-吡啶基、6-溴-3-吡啶基、2-氯-5-嘧啶基。
(4)提供如(1)或(3)中記載之有害生物防治用組成物,其中,式(I)中之A係次式(A-1):
Y係氫原子、鹵素原子、氰基。
(5)提供如(1)、或(3)~(4)中記載之有害生物防治用組成物,其中,式(I)中之R係式(c)之基
(6)提供如(1)、或(3)~(4)中記載之有害生物防治用組成物,其中,式(I)中之R係式(a)之基
(7)提供如(1)、或(3)~(4)中記載之有害生物防治用組成物,其中,式(I)中之R係式(d)之基
R4表示可經取代之C1~C18烷基、可經鹵素原子取代之C2~C6烯基、可經鹵素原子取代之C2~C6炔基、取代或無取代之(C6~C10)芳基、取代或無取代之(C6~C10)芳基(C1~C6)烷基、取代或無取代之(C6~C10)芳基(C2~C6)烯基、取代或無取代之(C6~C10)芳基(C2~C6)炔基、取代或無取代之苯氧基(C1~C6)烷基、取代或無取代之苯氧基(C2~C6)烯基、取代或無取代之苯氧基(C2~C6)炔基、取代或無取代之5~10員雜環、取代或無取代之5~10員雜環(C1~C6)烷基、取代或無取代之5~10員雜環(C2~C6)烯基、取代或無取代之5~10員雜環(C2~C6)炔基、(C1~C4)烷氧基(C1~C5)烷基、(C1~C4)烷氧基(C2~C5)烯基、(C1~C4)烷氧基(C2~C5)炔基、(C1~C4)烷硫基(C1~C5)烷基、(C1~C4)烷硫基(C2~C5)烯基、(C1~C4)烷硫基(C2~C5)炔基、R5表示可經鹵素原子取代之C1~C6烷基、可經鹵素原子取代之C2~C6烯基、可經鹵素原子取代之C2~C6炔基。
(8)提供如(1)中記載之有害生物防治用組成物,
其中,亞胺基吡啶衍生物係N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙醯胺、N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙硫醯胺、或N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟-N’-異丙基乙脒。
(9)提供一種自有害生物保護有用植物或動物之方法,其係含有將前述有害生物防治用組成物的有效量,對作為施用對象之有害生物、有用植物、有用植物的種子、土壤、栽培擔體、或動物進行處理所成者。
(10)提供一種組合物,其係含有前述式(I)所示之亞胺基吡啶衍生物與其他有害生物防治劑的至少1種所成。
(11)提供一種自有害生物保護有用植物或動物用的前述有害生物防治用組成物的使用。
藉由使用本發明之新穎亞胺基吡啶衍生物,係可更有效地進行小菜蛾、斜紋夜盗蛾、蚜蟲類、飛蝨類、葉蟬類、薊馬類、其他多數的有害生物的防治。
式(I)所示之新穎亞胺基吡啶衍生物,係可以下述之方法製造。
係使次式(II-1)所示之化合物與ArCH2X〔Ar、A、Y、R1的定義係與前述同義,X表示鹵素原子或OTs、OMs等〕所示之化合物在鹼存在下或非存在下反應。
在鹼存在下進行反應時,鹼方面,可使用例如氫化鈉等之鹼金屬氫化物、碳酸鉀或碳酸鈉等之碳酸鹽、氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物、三乙基胺、1,8-二氮雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲基胺基吡啶等之無取代或具有取代基之吡啶類。
反應係無溶媒或可使用對反應不影響之溶媒來進行,使用溶媒時,例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等之芳香族烴類、甲醇、乙醇、丙醇、異丙基醇等之醇類、丙酮、甲基乙基酮等之酮
類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類等之溶媒,可使用1種類或組合2種類以上使用,其中以使用N,N-二甲基甲醯胺等為佳。
反應通常可於0~200℃下進行,於20~40℃下加入試劑,於60~80℃下進行反應者為佳。
上述式(II-1)所示之化合物,係使後述之式(III)所示之化合物與R1-C(=O)X、R1-C(=O)OC(=O)R1、R1C(=O)OR’〔X表示鹵素原子或OTs、OMs等、R’表示C1~C6烷基、R1、A、Y、的定義表示與前述同義〕等所示之化合物在鹼存在下或非存在下反應。
在鹼存在下進行反應時,鹼方面,可使用例如氫化鈉等之鹼金屬氫化物、碳酸鉀或碳酸鈉等之碳酸鹽、氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物、三乙基胺、1,8-二氮雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲基胺基吡啶等之無取代或具有取代基之吡啶類。
反應係可無溶媒或使用對反應不影響之溶媒。使用溶媒時,例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯
類、苯、二甲苯、甲苯等之芳香族烴類、甲醇、乙醇、丙醇等之醇類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類、水等之溶媒,可使用1種類或組合2種類以上,但以使用甲苯、N,N-二甲基甲醯胺、乙腈、醚類、二氯甲烷、氯仿等者為佳。
反應通常可於-80~100℃下進行,較佳為於20~50℃之範圍下進行。
上述式(II-1)所示之化合物,係使上述式(III)所示之化合物與R1-COOH〔R1的定義表示與前述同義〕所示之羧酸,在鹼存在下或非存在下,使用脫水縮合劑來反應而得,或在鹼非存在下,使用五氧化磷、硫酸、聚磷酸、亞硫醯氯、氧氯化磷、草醯氯來反應而得。
脫水縮合劑方面,可使用二環己基碳二醯亞胺、1-乙基-3-(3-二甲基胺基丙基)碳二醯亞胺鹽酸鹽等之碳二醯亞胺系化合物等。
在鹼存在下進行反應時,鹼方面,可使用例如碳酸鉀或碳酸鈉等之碳酸鹽、三乙基胺、1,8-二氮雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲基胺基吡啶等之無取代或具有取代基之吡啶類等。
反應係以使用溶媒來進行者為佳,例如,N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等
之芳香族烴類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類,可使用1種類或組合2種類以上,但以使用二氯甲烷、氯仿等較佳。
反應通常可於-80~100℃下進行,較佳為於20~50℃之範圍下進行。
上述式(I-1)所示之化合物,係對次式(IV)所示之化合物使R1-C(=O)X、R1-C(=O)OC(=O)R1、R1C(=O)OR’〔X表示鹵素原子或OTs、OMs等、R’表示C1~C6烷基、Ar、A、Y、R1的定義表示與前述同義〕等所示之化合物在鹼存在下或非存在下反應。
在鹼存在下進行反應時,鹼方面,可使用例如氫化鈉等之鹼金屬氫化物、碳酸鉀或碳酸鈉等之碳酸鹽、氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物、三乙基胺、1,8-二氮雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲基胺基吡啶等之無取代或具有取代基之吡啶類。
反應係可無溶媒或使用對反應不影響之溶媒。使用溶媒時,例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯
類、苯、二甲苯、甲苯等之芳香族烴類、甲醇、乙醇、丙醇等之醇類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類、水等之溶媒,可使用1種類或組合2種類以上,但以使用甲苯、N,N-二甲基甲醯胺、乙腈、醚類、二氯甲烷、氯仿等者為佳。
反應通常可於-80~100℃下進行,較佳為於20~50℃之範圍下進行。
上述式(I-1)所示之化合物,係使前述式(IV)所示之化合物與R1-COOH〔R1-的定義表示與前述同義〕所示之羧酸,在鹼存在下或非存在下,使用脫水縮合劑反應而得,或在鹼非存在下,使用五氧化磷、硫酸、聚磷酸、亞硫醯氯、氧氯化磷、草醯氯來反應而得。
脫水縮合劑方面,可使用二環己基碳二醯亞胺、1-乙基-3-(3-二甲基胺基丙基)碳二醯亞胺鹽酸鹽等之碳二醯亞胺系化合物等。
在鹼存在下進行反應時,鹼方面,可使用例如碳酸鉀或碳酸鈉等之碳酸鹽、三乙基胺、1,8-二氮雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲基胺基吡啶等之無取代或具有取代基之吡啶類等。
反應係以使用溶媒來進行者為佳,例如,N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等
之芳香族烴類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類,可使用1種類或組合2種類以上,但以使用二氯甲烷、氯仿等較佳。
反應通常可於-80~100℃下進行,較佳為於20~50℃之範圍下進行。
上述式(IV)所示之化合物,係使前述式(III)所示之化合物與ArCH2X〔Ar、X的定義表示與前述同義〕所示之化合物,在鹼存在下或非存在下反應而得。
在鹼存在下進行反應時,鹼方面,可使用例如氫化鈉等之鹼金屬氫化物、碳酸鉀或碳酸鈉等之碳酸鹽、氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物、三乙基胺、1,8-二氮雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲基胺基吡啶等之無取代或具有取代基之吡啶類。
反應係可無溶媒或使用對反應不影響之溶媒。使用溶媒時,例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等之芳香族烴類、甲醇、乙醇、丙醇等之醇類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類、水等之溶媒,可使用1種類或組合2種類以上,但以使用N,N-二甲基甲醯胺、乙腈、醚類、二氯甲烷、氯仿等者較佳。
反應通常可於-80~100℃下進行,較佳係於20~80℃之範圍下進行者為佳。
自式(III)所示之化合物經式(II-1)來合成式(I-1)時,或是自式(III)所示之化合物經式(IV)來合成式(I-1)時,並不取出式(II-1)或是式(IV),而可連續地反應,又可自式(III)至式(I-1)為止於同一容器內同時進行。
上述式(I-2)所示之化合物,係使下述式(I-2a)所示之化合物與ArCH2X〔Ar、A、Y、R2的定義係與前述同義,X表示鹵素原子或OTs、OMs等〕所示之化合物,在鹼存在下或非存在下反應而得。
在鹼存在下進行反應時,鹼方面,可使用例如氫化鈉等之鹼金屬氫化物、碳酸鉀或碳酸鈉等之碳酸鹽、氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物、三乙基胺、1,8-二氮雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲
基胺基吡啶等之無取代或具有取代基之吡啶類。
反應係無溶媒或可使用對反應不影響之溶媒來進行,使用溶媒時,例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等之芳香族烴類、甲醇、乙醇、丙醇、異丙基醇等之醇類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類等之溶媒,可使用1種類或組合2種類以上使用,其中以使用N,N-二甲基甲醯胺等為佳。
反應通常可於0~200℃下進行,於20~40℃下加入試劑,於60~80℃下進行反應者為佳。
式(I-2a)所示之化合物,係使前述式(III)所示之化合物與R2OC(=O)X(R2、X的定義表示與前述同義)、或下述式(I-2b)所示之化合物,在鹼存在下或非存在下反應而得。
在鹼存在下進行反應時,鹼方面,可使用例如氫化鈉等之鹼金屬氫化物、碳酸鉀或碳酸鈉等之碳酸鹽、氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物、三乙基胺、1,8-二氮
雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲基胺基吡啶等之無取代或具有取代基之吡啶類。
反應係無溶媒或可使用對反應不影響之溶媒來進行,使用溶媒時,例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等之芳香族烴類、甲醇、乙醇、丙醇、異丙基醇等之醇類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類等之溶媒,可使用1種類或組合2種類以上,但以使用乙腈或二氯甲烷等者為佳。
反應通常可於0~200℃下進行,以20~80℃下進行反應者為佳。
式(I-2)所示之化合物,係使前述式(IV)所示之化合物與R2OC(=O)X(R2、X的定義表示與前述同義)、或前述式(I-2b)所示之化合物,在鹼存在下或非存在下反應而得。
在鹼存在下進行反應時,鹼方面,可使用例如氫化鈉等之鹼金屬氫化物、碳酸鉀或碳酸鈉等之碳酸鹽、氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物、三乙基胺、1,8-二氮雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲基胺基吡啶等之無取代或具有取代基之吡啶類。
反應係無溶媒或可使用對反應不影響之溶媒來進行,使用溶媒時,例如N,N-二甲基甲醯胺、N,N-二甲基乙醯
胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等之芳香族烴類、甲醇、乙醇、丙醇、異丙基醇等之醇類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類等之溶媒,可使用1種類或組合2種類以上,但以使用乙腈或二氯甲烷等者為佳。
反應通常可於0~200℃下進行,以20~80℃下進行反應者為佳。
上述式(I-3)所示之化合物,係對可與式(I-1)中記載之方法同樣地合成之下述式(II-3a)所示之化合物(Ar、A、Y、R3的定義表示與前述同義),在鹼存在下或非存在化下,使硫化試劑作用來合成。
在鹼存在下進行反應時,鹼方面,雖可使用例如氫化鈉等之鹼金屬氫化物、碳酸鉀或碳酸鈉等之碳酸鹽、氫氧
化鉀、氫氧化鈉等之鹼金屬氫氧化物、三乙基胺、1,8-二氮雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲基胺基吡啶等之無取代或具有取代基之吡啶類等,但以使用碳酸鉀或碳酸鈉等者為佳。
硫化試劑方面,可使用五硫化二磷、勞森試劑、硫化氫等。
反應係無溶媒或可使用對反應不影響之溶媒來進行,使用溶媒時,例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等之芳香族烴類、甲醇、乙醇、丙醇等之醇類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類等之溶媒,可使用1種類或組合2種類以上,但以使用甲苯、四氫呋喃等者為佳。
反應通常可於-80~100℃下進行,較佳係於20~80℃之範圍下進行者為佳。
式(I-3)所示之化合物,係使次式(II-3b)所示之化合物與ArCH2X〔Ar、A、Y、R3的定義係與前述同義,X表示鹵素原子或OTs、OMs等〕所示之化合物在鹼存在下或非存在下反應。
在鹼存在下進行反應時,鹼方面,可使用例如氫化鈉等之鹼金屬氫化物、碳酸鉀或碳酸鈉等之碳酸鹽、氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物、三乙基胺、1,8-二氮雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲基胺基吡啶等之無取代或具有取代基之吡啶類。
反應係無溶媒或可使用對反應不影響之溶媒來進行,使用溶媒時,例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等之芳香族烴類、甲醇、乙醇、丙醇、異丙基醇等之醇類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類等之溶媒,可使用1種類或組合2種類以上使用,其中以使用N,N-二甲基甲醯胺等為佳。
反應通常可於0~200℃下進行,於20~40℃下加入試劑,於60~80℃下進行反應者為佳。
上述式(II-3b)所示之化合物,係對可與式(II-1)中記載之方法同樣地合成之式(II-3c)所示之化合物
(A、Y、R3的定義表示與前述同義),在鹼存在下或非存在化下,使硫化試劑作用來合成。
在鹼存在下進行反應時,鹼方面,雖可使用例如氫化鈉等之鹼金屬氫化物、碳酸鉀或碳酸鈉等之碳酸鹽、氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物、三乙基胺、1,8-二氮雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲基胺基吡啶等之無取代或具有取代基之吡啶類等,但以使用碳酸鉀或碳酸鈉等者為佳。
硫化試劑方面,可使用五硫化二磷、勞森試劑、硫化氫等。
反應係無溶媒或可使用對反應不影響之溶媒來進行,使用溶媒時,例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等之芳香族烴類、甲醇、乙醇、丙醇等之醇類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類等之溶媒,可使用1種類或組合2種類以上,但以使用甲苯、四氫呋喃等者為佳。
反應通常可於-80~100℃下進行,較佳係於20~80℃之範圍下進行者為佳。
上述式(I-4)所示之化合物,係可使以式(I-3)中記載之方法可合成之下述式(II-4a)所示之化合物與R4-NH2(Ar、A、Y、R4、R5的定義表示與前述同義)所示之化合物反應而得。
反應係無溶媒或可使用對反應不影響之溶媒來進行,使用溶媒時,例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等之芳香族烴類、甲醇、乙醇、丙醇等之醇類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類等之溶媒,可使用1種類或組合2種類以
上,但以使用甲醇、乙醇等的醇類者為佳。
反應若於碳酸銀、碳酸銅等的存在下可快速進行,若無亦可進行。
反應通常可於-80~100℃下進行,較佳係於20~80℃之範圍下進行者為佳。
式(I-4)所示之化合物,係使下述式(I-4b)所示之化合物或其鹽與R4-X、R4-O-R4、R4-OR’(R4、R’、Ar、A、Y、R5的定義係與前述同義,X表示鹵素原子),在鹼存在下或非存在下反應而得。
在鹼存在下進行反應時,鹼方面,可使用例如氫化鈉等之鹼金屬氫化物、碳酸鉀或碳酸鈉等之碳酸鹽、氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物、三乙基胺、1,8-二氮雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲基胺基吡啶等之無取代或具有取代基之吡啶類。
反應係可無溶媒或使用對反應不影響之溶媒。使用溶媒時,例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等之芳香族烴類、甲醇、乙醇、丙醇等之醇類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、
辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類、水等之溶媒,可使用1種類或組合2種類以上,但以使用甲苯、二甲基甲醯胺、乙腈、醚類、二氯甲烷、氯仿等者為佳。
反應通常可於-80~100℃下進行,較佳為於20~50℃之範圍下進行。
式(I-4b)所示之化合物係可使式(II-4a)所示之化合物與氨或其醇溶液、氯化銨等反應而得。
反應係可無溶媒或使用對反應不影響之溶媒。使用溶媒時,例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等之芳香族烴類、甲醇、乙醇、丙醇等之醇類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類、水等之溶媒,可使用1種類或組合2種類以上,但以使用甲醇、乙醇等的醇類者為佳。
反應通常可於-80~100℃下進行,較佳為於20~50℃之範圍下進行。
上述式(I-5)所示之化合物,係使下述式(II-5b)
所示之化合物與R6-X(Ar、A、Y、R6、R7的定義係與前述同義,X表示鹵素原子)、R6-O-R6、或R6-OR’(R’的定義表示與前述同義),在鹼存在下或非存在下反應而得。
在鹼存在下進行反應時,鹼方面,可使用例如氫化鈉等之鹼金屬氫化物、碳酸鉀或碳酸鈉等之碳酸鹽、氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物、三乙基胺、1,8-二氮雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲基胺基吡啶等之無取代或具有取代基之吡啶類。
反應係可無溶媒或使用對反應不影響之溶媒。使用溶媒時,例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等之芳香族烴類、甲醇、乙醇、丙醇等之醇類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類、水等之溶媒,可使用1種類或組合2種類以上,但以使用甲苯、N,N-二甲基甲醯胺、乙腈、醚類、二氯甲烷、氯仿等者為佳。
反應通常可於-80~100℃下進行,較佳為於20~50℃之範圍下進行。
R6表示-C(=O)R6a(R6a表示與前述同義)時,式(I-5)所示之化合物,係使式(II-5b)所示之化合物與R6a-C(=O)OH(R6a的定義表示與前述同義)所示之羧酸,在鹼存在下或非存在下,使用脫水縮合劑反應而得,或在鹼非存在下,使用五氧化磷、硫酸、聚磷酸、亞硫醯氯、氧氯化磷、草醯氯來反應而得。
脫水縮合劑方面,可使用二環己基碳二醯亞胺、1-乙基-3-(3-二甲基胺基丙基)碳二醯亞胺鹽酸鹽等之碳二醯亞胺系化合物等。
在鹼存在下進行反應時,鹼方面,可使用例如碳酸鉀或碳酸鈉等之碳酸鹽、三乙基胺、1,8-二氮雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲基胺基吡啶等之無取代或具有取代基之吡啶類等。
反應係以使用溶媒來進行者為佳,例如,N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等之芳香族烴類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類,可使用1種類或組合2種類以上,但以使用二氯甲烷、氯仿等較佳。
反應通常可於-80~100℃下進行,較佳為於20~50℃
之範圍下進行。
R6表示CONR6eR6f(R6e、R6f的定義係與前述同義,R6e或R6f中任一者表示氫原子)或CSNR6gR6h(R6g、R6h的定義係與前述同義,R6g或R6h中任一者表示氫原子)時,式(I-5)之化合物係於式(II-5b)中使R”N=C=O(R”表示可藉由鹵素原子所經取代的C1~C6烷基、可藉由鹵素原子所經取代的C2~C6烯基、可藉由鹵素原子所經取代的C2~C6炔基、(C1~C4)烷氧基(C1~C5)烷基、(C1~C4)烷硫基(C1~C5)烷基、取代或無取代之(C6~C10)芳基、取代或無取代之5~10員雜環)所示之化合物,在鹼存在下或非存在下反應而得。
在鹼存在下進行反應時,鹼方面,可使用例如氫化鈉等之鹼金屬氫化物、碳酸鉀或碳酸鈉等之碳酸鹽、氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物、三乙基胺、1,8-二氮雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲基胺基吡啶等之無取代或具有取代基之吡啶類。
反應係以使用溶媒來進行者為佳,例如,N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等之芳香族烴類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類,可使用1種類或組合2種類以上,但以使
用乙腈等之腈類者為佳。
反應通常可於-80~100℃下進行,較佳係於20~80℃之範圍下進行者為佳。
R6表示CONR6eR6f(R6e、R6f的定義表示與前述同義)時,式(I-5)之化合物,係使前述式(II-5b)所示之化合物與下述式(II-5c)所示之化合物,在鹼存在下或非存在下反應而得。
在鹼存在下進行反應時,鹼方面,可使用例如氫化鈉等之鹼金屬氫化物、碳酸鉀或碳酸鈉等之碳酸鹽、氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物、三乙基胺、1,8-二氮雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲基胺基吡啶等之無取代或具有取代基之吡啶類。
反應係以使用溶媒來進行者為佳,例如,N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等之芳香族烴類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類,可使用1種類或組合2種類以上,但以使用乙腈等之腈類者為佳。
反應通常可於-80~100℃下進行,較佳係於20~80℃之範圍下進行者為佳。
式(II-5b)所示之化合物,係使可以與式(I-3)中記載之方法同樣地合成之式(II-5a)所示之化合物(Ar、A、Y、R7的定義表示與前述同義)與羥基胺或其鹽,在鹼存在下或非存在下反應而得。
在鹼存在下進行反應時,鹼方面,可使用例如氫化鈉等之鹼金屬氫化物、碳酸鉀或碳酸鈉等之碳酸鹽、氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物、三乙基胺、1,8-二氮雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲基胺基吡啶等之無取代或具有取代基之吡啶類。
反應係可無溶媒或使用對反應不影響之溶媒。使用溶媒時,例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等之芳香族烴類、甲醇、乙醇、丙醇等之醇類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類、水等之溶媒,可使用1種類或組合2種類以
上,但以使用甲苯、N,N-二甲基甲醯胺、乙腈、醚類、二氯甲烷、氯仿等者為佳。
反應通常可於-80~100℃下進行,較佳係於20~80℃之範圍下進行者為佳。
式(I-5)所示之化合物,係使式(II-5a)所示之化合物與R6-ONH2所示之化合物或其鹽,在鹼存在下或非存在下反應而得。
在鹼存在下進行反應時,鹼方面,可使用例如氫化鈉等之鹼金屬氫化物、碳酸鉀或碳酸鈉等之碳酸鹽、氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物、三乙基胺、1,8-二氮雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲基胺基吡啶等之無取代或具有取代基之吡啶類。
反應係可無溶媒或使用對反應不影響之溶媒。使用溶媒時,例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等之芳香族烴類、甲醇、乙醇、丙醇等之醇類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類、水等之溶媒,可使用1種類或組合2種類以上,但以使用甲醇、乙醇等的醇類者為佳。
反應通常可於-80~100℃下進行,較佳係於20~80℃之範圍下進行者為佳。
反應若於碳酸銀、碳酸銅等的存在下可快速進行,若
無亦可進行。
上述式(I-6)所示之化合物〔Ar、A、Y、Ry、Y1、Y2的定義表示與前述同義〕係可依據“Phosphorus,sulfur,and silicon and the related elements”,(2006)181,2337-2344中記載之方法來合成。
上述式(I-7)所示之化合物〔Ar、A、Y、Rz、n的定義表示與前述同義〕係使下述式(II-7a)〔A、Y、Rz、n的定義表示與前述同義〕所示之化合物與ArCH2X〔Ar的定義係與前述同義,X表示鹵素原子或OTs、OMs等〕所示之化合物在鹼存在下或非存在下反應。
在鹼存在下進行反應時,鹼方面,可使用例如氫化鈉等之鹼金屬氫化物、碳酸鉀或碳酸鈉等之碳酸鹽、氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物、三乙基胺、1,8-二氮雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲基胺基吡啶等之無取代或具有取代基之吡啶類。
反應係無溶媒或可使用對反應不影響之溶媒來進行,使用溶媒時,例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等之芳香族烴類、甲醇、乙醇、丙醇、異丙基醇等之醇類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類等之溶媒,可使用1種類或組合2種類以上使用,其中以使用N,N-二甲基甲醯胺等為佳。
反應通常可於0~200℃下進行,於20~40℃下加入試劑,於60~80℃下進行反應者為佳。
又,式(II-7a)所示之化合物,係使前述式(III)所示之化合物與式(II-7b)(Rz、n的定義係與前述相同、
X表示鹵素原子)所示之化合物,在鹼存在下或非存在下反應而得。
在鹼存在下進行反應時,鹼方面,可使用例如氫化鈉等之鹼金屬氫化物、碳酸鉀或碳酸鈉等之碳酸鹽、氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物、三乙基胺、1,8-二氮雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲基胺基吡啶等之無取代或具有取代基之吡啶類。
反應係無溶媒或可使用對反應不影響之溶媒來進行,使用溶媒時,例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等之芳香族烴類、甲醇、乙醇、丙醇、異丙基醇等之醇類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類等之溶媒,可使用1種類或組合2種類以上使用,其中以使用N,N-二甲基甲醯胺等為佳。
反應通常可於0~200℃下進行,於20~40℃下加入試劑,於60~80℃下進行反應者為佳。
式(I-7)所示之化合物,係使前述式(IV)所示之化合物與式(II-7b)所示之化合物,在鹼存在下或非存在
下反應而得。
在鹼存在下進行反應時,鹼方面,可使用例如氫化鈉等之鹼金屬氫化物、碳酸鉀或碳酸鈉等之碳酸鹽、氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物、三乙基胺、1,8-二氮雜雙環〔4.3.0〕壬-5-烯等之第3級胺類、吡啶、4-二甲基胺基吡啶等之無取代或具有取代基之吡啶類。
反應係無溶媒或可使用對反應不影響之溶媒來進行,使用溶媒時,例如N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類、乙腈等之腈類、二甲基亞碸等之亞碸類、二乙基醚、四氫呋喃等之醚類、醋酸乙基酯、醋酸丁基酯等之酯類、苯、二甲苯、甲苯等之芳香族烴類、甲醇、乙醇、丙醇、異丙基醇等之醇類、丙酮、甲基乙基酮等之酮類、己烷、庚烷、辛烷等之脂肪族烴類、二氯甲烷、氯仿、氯苯、二氯苯等之鹵烴類等之溶媒,可使用1種類或組合2種類以上使用,其中以使用N,N-二甲基甲醯胺等為佳。
反應通常可於0~200℃下進行,於0~80℃下進行反應者為佳。
Ar表示之「可經取代之苯基」、「可經取代之5~6員之雜環」之可經取代之取代基方面,可舉出鹵素原子、可經鹵素原子取代之C1~C4烷基、可經鹵素原子取代之C1~C4烷基氧基、羥基、氰基、硝基等,較佳為鹵素原子、三氟甲基、氰基,特佳為鹵素原子。
式(I)所示之具有2-亞胺基之含氮雜環衍生物化合
物的Ar表示之「可經取代之苯基」的具體例方面,苯基、3-氰基苯基。
式(I)所示之具有2-亞胺基之含氮雜環衍生物化合物的Ar表示之「可經取代之5~6員之雜環」,表示含有1個~2個的氧原子、硫原子、或氮原子等雜原子之芳香族5~6員雜環,具體而言,可舉出吡啶環、吡嗪環、嘧啶環、嗒嗪環、噻唑環、噁唑環等,較佳樣態方面,係6-氯-3-吡啶基、6-氯-5-氟-3-吡啶基、6-溴-3-吡啶基、6-氟-3-吡啶基、6-三氟甲基-3-吡啶基、6-氯-3-吡嗪基、5-氯-2-吡嗪基、2-氯-5-嘧啶基、2-氯-5-噻唑基、2-氯-4-吡啶基,更佳為6-氯-3-吡啶基、6-氟-3-吡啶基、6-氯-5-氟-3-吡啶基、6-溴-3-吡啶基、2-氯-5-嘧啶基。
式(I)所示之具有2-亞胺基之含氮雜環衍生物的Ar所示之「4~10員之雜環烷基」,具體而言,可舉出2-四氫呋喃基、3-四氫呋喃基等,較佳為3-四氫呋喃基。
式(I)所示之具有2-亞胺基之含氮雜環衍生物的A表示之「含1個以上氮原子之5~10員具不飽和鍵結之雜環」,是謂式(I)中之
表示下述各式A-1~A-40所示之任一的環。各式中,雙鍵的先端為氮原子的取代位置。
較佳為上式A-1、A-13、A-14、A-15、A-16、A-23、A-25、A-38、A-39之環,更佳為上式A-1之環。
Y表示之「可經鹵素原子取代之C1~C6烷基」,是謂鏈狀、分支狀、環狀或該等的組合之碳數1~6之烷基、可經取代之鹵素原子的數目之上限,為烷基所有氫原子之數。含有分支狀或環狀之烷基時,已知碳數為3以上。
Y表示之「可經鹵素原子取代之C1~C6烷基氧基」,具體而言,可舉出甲氧基、乙氧基、三氟甲基氧基、二氟甲基氧基。
Y的較佳樣態方面係氫原子、或鹵素原子,更佳為氫原子。
R的較佳樣態方面,可舉出前述式(a)或式(c)所示之基,且式(I)中,R1表示之「已經取代之C1~C6烷基」,是謂鏈狀、分支狀、環狀或該等的組合之碳數1~6之烷基,且已經取代之取代基的數目之上限,為烷基所有氫原子之數。已經取代之取代基方面,可舉出鹵素原子、羥基、氰基、硝基、苯基(此苯基係可以可經鹵素所取代之C1~C4烷基、可經鹵素所取代之C1~C4烷氧基、羥基、鹵素原子等所取代)、苯氧基(此苯基係可以可經鹵素所取代之C1~C4烷基、可經鹵素所取代之C1~C4烷氧基、羥基、鹵素原子等所取代)、苯甲基氧基(此苯甲基氧基中之苯基係可以可經鹵素所取代之C1~C4烷基、可經鹵素所取代之C1~C4烷氧基、羥基、鹵素原子等所取代)等。具體而言,可舉出1,1,1-三氟乙基、三氟甲基、三氯甲基、二氟氯甲基、二氟甲基、二氯甲基、二溴甲基、氯甲基、二氟乙基、二氯乙基、2,2,2-三氟乙基、五氟乙基、二氟環丙基、2-氰基乙基、2-硝基乙基等。較佳為1,1,1-三氟乙基、三氟甲基、二氟氯甲基、二氟甲基、五氟乙基,更佳為三氟甲基、二氟氯甲基、二氟甲基、五氟乙基,特佳為三氟甲基。
式(I)中,R3、R5、R7、Ry、Rz表示之「可經鹵素原子取代之C1~C6烷基」,是謂鏈狀、分支狀、環狀或該等的組合之碳數1~6之烷基,且已經取代之鹵素原子的數目之上限,為烷基所有氫原子之數。含有分支狀或環狀之烷基時,已知碳數為3以上。具體而言,可舉出甲基、乙基、n-丙基、異丙基、n-丁基、t-丁基、環丙基、環戊基、環己基、三氟甲基、三氯甲基、二氟氯甲基、二氟甲基、二氯甲基、二溴甲基、氯甲基、二氟乙基、二氯乙基、2,2,2-三氟乙基、五氟乙基、二氟環丙基、三氟異丙基、六氟異丙基等。
R3較佳為乙基、異丙基、環丙基、三氟甲基、二氟氯甲基、二氟甲基、五氟乙基,更佳為三氟甲基、二氟氯甲基、二氟甲基、五氟乙基,特佳為三氟甲基。R5較佳為三氟甲基、三氯甲基、二氯甲基、二氟甲基、二氟氯甲基、氯甲基、五氟乙基,更佳為三氟甲基、二氟甲基、二氟氯甲基、五氟乙基,特佳為三氟甲基。R7較佳為三氟甲基、三氯甲基、二氯甲基、二氟甲基、二氟氯甲基、氯甲基、五氟乙基,更佳為三氟甲基、二氟甲基、二氟氯甲基、五氟乙基,特佳為三氟甲基。Ry較佳為甲基、乙基、丙基、異丙基。Rz較佳為甲基、三氟甲基。
R2表示之「已經鹵素原子取代之C1~C6烷基」,是謂鏈狀、分支狀、環狀或該等的組合之碳數1~6之烷基,且已經取代之鹵素原子的數目之上限,為烷基所有氫原子之數。含有分支狀或環狀之烷基時,已知碳數為3以
上。具體而言,可舉出三氟甲基、三氯甲基、二氟氯甲基、二氟甲基、二氯甲基、二溴甲基、氯甲基、二氟乙基、二氯乙基、2,2,2-三氟乙基、五氟乙基、二氟環丙基、1-(三氟甲基)乙基、1-三氟甲基-2,2,2-三氟乙基等,較佳為2,2,2-三氟乙基、1-(三氟甲基)乙基、1-三氟甲基-2,2,2-三氟乙基、五氟乙基、二氟環丙基等。在此較佳的烷基為2,2,2-三氟乙基、1-(三氟甲基)乙基、1-三氟甲基-2,2,2-三氟乙基。
R4、R6表示之「可經取代之C1~C18烷基」,是謂鏈狀、分支狀、環狀或該等的組合之碳數1~18之烷基、可經取代的取代基的數目之上限,為烷基所有氫原子之數。
含有分支狀或環狀之烷基時,已知碳數為3以上。可經取代的取代基方面,可舉出鹵素原子、羥基、氰基、硝基等。具體而言,可舉出甲基、乙基、n-丙基、異丙基、n-丁基、s-丁基、t-丁基、3-甲基-2-丁基、3-戊基、4-庚基、環丙基、環丁基、環戊基、環己基、n-辛基、n-十三基、n-十六基、n-十八基、三氟甲基、三氯甲基、二氟氯甲基、二氟甲基、二氯甲基、二溴甲基、氯甲基、二氟乙基、二氯乙基、2,2,2-三氟乙基、五氟乙基、二氟環丙基、2-羥基乙基、2-羥基-n-丙基、3-羥基-n-丙基、2,3-二羥基-n-丙基、氰基甲基、2-氰基乙基、2-硝基乙基等。
R4較佳為甲基、乙基、2,2,2-三氟乙基、2,2-二氟乙基、n-丙基、異丙基、環丙基、t-丁基、環丁基、環戊
基、環己基、2-羥基乙基,更佳為甲基、乙基、異丙基、n-丙基、環丙基、環丁基、環戊基、環己基。R6較佳為甲基、乙基、異丙基、環丙基、t-丁基、氰基甲基,更佳為甲基、乙基、環丙基、t-丁基。
R4a、R4b、R4c、R4d、R4e、R4f、R6a、R6b、R6c、R6d、R6e、R6f、R6g、R6h、R6i、R6j、R6k表示之「可經鹵素原子取代之C1~C6烷基」,是謂鏈狀、分支狀、環狀或該等的組合之碳數1~6之烷基,且已經取代之鹵素原子的數目之上限,為烷基所有氫原子之數。含有分支狀或環狀之烷基時,已知碳數為3以上。具體而言,可舉出甲基、乙基、n-丙基、異丙基、n-丁基、t-丁基、環丙基、環戊基、環己基、三氟甲基、三氯甲基、二氟氯甲基、二氟甲基、二氯甲基、二溴甲基、氯甲基、二氟乙基、2-氯乙基、二氯乙基、2,2,2-三氟乙基、五氟乙基、二氟環丙基等。R6a較佳為甲基、乙基、異丙基、環丙基。R6b較佳為甲基。
R1、R2、R3、R4、R4a、R4b、R4c、R4d、R4e、R4f、R5、R6、R6a、R6b、R6c、R6d、R6e、R6f、R6g、R6h、R6i、R6j、R6k、R7、Ry、Rz表示之「可經鹵素原子取代之C2~C6烯基」,是謂鏈狀、分支狀、環狀或該等的組合之碳數2~6之烯基,且已經取代之鹵素原子的數目之上限係烯基所有氫原子之數。含有分支狀或環狀之烯基時,已知碳數為3以上。具體而言,可舉出乙烯基、1-丙烯基、2-丙烯基、2-氟-1-丙烯基、2-甲基-1-丙烯基
等,較佳為乙烯基。
R1、R2、R3、R4、R4a、R4b、R4c、R4d、R4e、R4f、R5、R6、R6a、R6b、R6c、R6d、R6e、R6f、R6g、R6h、R6i、R6j、R6k、R7、Ry、Rz表示之「可經鹵素原子取代之C2~C6炔基」,是謂鏈狀、分支狀、或該等的組合之碳數2~6之炔基,且已經取代之鹵素原子的數目之上限係炔基所有氫原子之數。含有分支狀或環狀之炔基時,已知碳數為3以上。具體而言,可舉出1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、1-戊炔基、2-戊炔基、3-戊炔基等,較佳為1-丙炔基、2-丙炔基、2-丁炔基。
R2、R3、R4、R4a、R4b、R4c、R5、R6、R6a、R6b、R6c、R7、Ry、Rz表示之「取代或無取代之(C6~C10)芳基、取代或無取代之(C6~C10)芳基(C1~C6)烷基、取代或無取代之(C6~C10)芳基(C2~C6)烯基、取代或無取代之(C6~C10)芳基(C2~C6)炔基」之(C6~C10)芳基,具體而言,表示苯基、萘基,且(C1~C6)烷基、(C2~C6)烯基、(C2~C6)炔基亦可具有直鏈、分支或環。芳基上可取代的取代基方面,可舉出鹵素原子、可經鹵素所取代的C1~C4烷基、可經鹵素所取代的C1~C4烷基氧基、C3~C6之環狀烷基、甲基磺醯基、甲氧基、硝基、氰基等。具體而言,可舉出苯基、苯甲基、2-苯基乙基、2-苯基乙烯基、2-苯基乙炔基、4-甲基苯基、2-氰基苯基、3-氯苯基、4-甲氧基苯基、3-氰基苯基、1,1-二苯基甲基、萘基乙基、萘基丙基
等,較佳為苯甲基、2-苯基乙基、萘基乙基、萘基丙炔基。
R3、R4、R4a、R4b、R4c、R5、R6、R6a、R6b、R6c、R7、Ry、Rz表示之「取代或無取代之苯氧基(C1~C6)烷基、取代或無取代之苯氧基(C2~C6)烯基、取代或無取代之苯氧基(C2~C6)炔基」之(C1~C6)烷基、(C2~C6)烯基、(C2~C6)烯基亦可具有直鏈、分支或環。苯氧基上可取代的取代基方面,可舉出鹵素原子、可經鹵素所取代的C1~C4烷基、可經鹵素所取代的C1~C4烷基氧基、C3~C6之環狀烷基、甲基磺醯基、甲氧基、硝基、氰基等。具體而言,可舉出苯氧基、苯氧基甲基、2-苯氧基乙基、2-苯氧基乙烯基、2-苯氧基乙炔基、4-氯苯氧基、2-甲基苯氧基等,較佳為2-苯氧基乙基。
R2、R3、R4、R4a、R4b、R4c、R5、R6、R6a、R6b、R6c、R7、Ry、Rz表示之「取代或無取代之5~10員雜環、取代或無取代之5~10員雜環(C1~C6)烷基、取代或無取代之5~10員雜環(C2~C6)烯基、取代或無取代之5~10員雜環(C2~C6)炔基」之5~10員雜環,是謂構成環之原子方面,表示含1個~4個氧原子、硫原子或氮原子等的雜原子之環,可舉例如呋喃基、噻吩基、吡啶基、吡咯啶基、哌啶基、哌嗪基、嘧啶基、嗎啉基、噻唑基、咪唑基、三唑基、四氫呋喃基、喹啉基等。雜環上可取代的取代基方面,可舉出鹵素原子、可經
鹵素所取代的C1~C4烷基、可經鹵素所取代的C1~C4烷基氧基、C3~C6之環狀烷基、甲基磺醯基、甲氧基、硝基、氰基等。(C1~C6)烷基、(C2~C6)烯基、(C2~C6)烯基亦可具有直鏈、分支或環。具體而言,可舉出2-吡啶基、3-吡啶基、4-吡啶基、2-吡啶基甲基、3-吡啶基甲基、4-吡啶基甲基、2-(4-吡啶基)乙烯基、2-(4-吡啶基)乙炔基、2-呋喃基甲基、2-噻吩基甲基、2-四氫呋喃基甲基等,較佳為2-吡啶基甲基、3-吡啶基甲基、4-吡啶基甲基、2-呋喃基甲基、2-噻吩基甲基、2-四氫呋喃基甲基。
R3、R4、R4a、R4b、R4c、R5、R6、R6a、R6b、R6c、R6e、R6f、R7、Rz表示之「(C1~C4)烷氧基(C1~C5)烷基、(C1~C4)烷氧基(C2~C5)烯基、(C1~C4)烷氧基(C2~C5)炔基」之(C1~C4)烷氧基,表示具有直鏈、分支或環之(C1~C4)烷基氧基、烯基氧基、炔基氧基。具體而言,為甲氧基甲基、2-甲氧基乙基、乙氧基甲基、2-乙氧基乙基、3-甲氧基-2-丙烯基、3-甲氧基-2-丙炔基等,R4較佳為2-甲氧基乙基。
R3、R4、R4a、R4b、R4c、R5、R6、R6a、R6b、R6c、R6e、R6f、R7、Rz表示之「(C1~C4)烷硫基(C1~C5)烷基、(C1~C4)烷硫基(C2~C5)烯基、(C1~C4)烷硫基(C2~C5)炔基」之(C1~C4)烷硫基,表示具有直鏈、分支或環之(C1~C4)烷硫基、烯硫基、炔硫基。具體而言,為甲硫基甲基、2-甲硫基乙
基、乙硫基甲基、2-乙硫基乙基、3-甲硫基-2-丙烯基、3-甲硫基-2-丙炔基等,R4較佳為2-甲硫基乙基。
R2、R4d、R4e、R4f、R6d、R6e、R6f、R6g、R6h、R6i、R6j、R6k表示之「取代或無取代之(C6~C10)芳基」之(C6~C10)芳基,具體而言,表示苯基、萘基,且(C1~C6)烷基、(C2~C6)烯基、(C2~C6)烯基亦可具有直鏈、分支或環。芳基上可取代的取代基方面,可舉出鹵素原子、可經鹵素所取代的C1~C4烷基、可經鹵素所取代的C1~C4烷基氧基、C3~C6之環狀烷基、甲基磺醯基、甲氧基、硝基、氰基等。具體而言,可舉出苯基、2-甲基苯基、3-甲氧基苯基、4-硝基苯基、4-氰基苯基等。
R2、R4d、R4e、R4f、R6d、R6e、R6f、R6g、R6h表示之「取代或無取代之5~10員雜環」之5~10員雜環,在構成環之原子方面,表示含1個~4個氧原子、硫原子或氮原子等的雜原子之環,可舉例如呋喃基、噻吩基、吡啶基、吡咯啶基、哌啶基、哌嗪基、嘧啶基、嗎啉基、噻唑基、咪唑基、三唑基、四氫呋喃基、喹啉基等。雜環上可取代的取代基方面,可舉出鹵素原子、可經鹵素所取代的C1~C4烷基、可經鹵素所取代的C1~C4烷基氧基、C3~C6之環狀烷基、甲基磺醯基、甲氧基、硝基、氰基等。具體而言,可舉出2-吡啶基、3-吡啶基、4-吡啶基、2-呋喃基、2-噻吩基、2-四氫呋喃基等。
式(I)所示之化合物的較佳樣態方面,係
R表示下述之式(a)
Ar表示6-氯-3-吡啶基、2-氯-5-噻唑基、6-氯-5-氟-3-吡啶基、6-氟-3-吡啶基、6-溴-3-吡啶基、2-氯-5-嘧啶基、6-三氟甲基-3-吡啶基、2-氯-5-嘧啶基、A表示A-1、A-13、A-14、A-15、A-16、A-23、A-38所示之環、Y表示氫原子、3-氰基、R1表示三氟甲基、二氟甲基、氯二氟甲基、五氟乙基、三氟乙基、乙烯基、2-丙炔基。
式(I)所示之化合物的別的較佳樣態方面,係R表示下述之式(c)
Ar表示6-氯-3-吡啶基、2-氯-5-噻唑基、6-氯-5-氟-3-吡啶基、6-氟-3-吡啶基、6-溴-3-吡啶基、2-氯-5-嘧啶基、6-三氟甲基-3-吡啶基、A表示A-1所示之環、Y表示氫原子、R3表示三氟甲基、二氟甲基、氯二氟甲基、五氟乙基。
式(I)所示之化合物的別的較佳樣態方面,係R表示下述之式(d)
Ar表示6-氯-3-吡啶基、6-氯-5-氟-3-吡啶基、6-氟-3-吡啶基、6-溴-3-吡啶基、2-氯-5-嘧啶基、A表示A-1所示之環、Y表示氫原子、R4表示氫原子、甲基、乙基、n-丙基、異丙基、環丙基、環丁基、環戊基、環己基、R5表示三氟甲基、二氟甲基、氯二氟甲基、五氟乙基。
式(I)所示之化合物的別的較佳樣態方面,係R表示下述之式(e)
Ar表示6-氯-3-吡啶基、6-氯-5-氟-3-吡啶基、6-氟-3-吡啶基、6-溴-3-吡啶基、2-氯-5-嘧啶基、A表示A-1所示之環、Y表示氫原子、
R6表示氫原子、甲基、乙基、2-丙烯基、甲基羰基、乙基羰基、環丙基羰基、乙烯基羰基、2-丙炔基羰基、苯甲醯基、3-吡啶基羰基、甲基氧基羰基、苯基氧基羰基、R7表示三氟甲基、二氟甲基、氯二氟甲基、五氟乙基。
式(I)之化合物的具體例方面,可舉出以下述之表A及表B的組合所示的化合物。
較佳之式(I)之化合物的例方面,可舉出下述表中所示之化合物。
更佳的化合物可舉出N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙醯胺(化合物P212)、N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞
基〕-2,2,2-三氟乙硫醯胺(化合物1-20)、N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟-N’-異丙基乙脒(化合物1-45)。
又,本發明中,亦可利用式(I)所示之新穎亞胺基吡啶衍生物的酸加成鹽(較佳為農畜藥上可容許之酸加成鹽),該例子方面,可舉出鹽酸鹽、硝酸鹽、硫酸鹽、磷酸鹽、或醋酸鹽等之酸加成鹽。
式(I)所示之新穎亞胺基吡啶衍生物,本身即對害蟲顯示出優異的防治效果,亦可藉由與其他有害生物防治劑混合使用,而顯示出較單劑使用更為優異之防治效果。因此,根據本發明,係可提供含有式(I)所示之新穎亞胺基吡啶衍生物的至少1種與其他有害生物防治劑的至少1種所成之有害生物防治用組成物。
再根據本發明,係可提供含有式(I)所示之新穎亞胺基吡啶衍生物的至少1種與其他的殺蟲劑及/或殺菌劑的至少1種所成之優異的有害生物防治用組成物。
藉由本發明所提供的有害生物防治用組成物方面,可舉例如農園藝用有害生物防治劑、動物寄生性害蟲防治劑、衛生害蟲防治劑、噁心害蟲防治劑、貯穀.貯蔵食品害蟲防治劑、家屋害蟲防治劑等,較佳為農園藝用有害生物防治劑、動物寄生性害蟲防治劑。
含有式(I)所示之新穎亞胺基吡啶衍生物、或該等之酸加成鹽的至少1種與其他有害生物防治劑的至少1種所成之有害生物防治用組成物,其能顯示出防治效果的蟲
種方面,可舉出鱗翅目害蟲(例如,斜紋夜盗蛾、夜盗蛾、黏蟲、螟蛉、小菜蛾、甜菜夜蛾、二化螟、瘤野螟、捲葉蛾、果蛀蛾、萊氏蛾、毒蛾、球菜夜蛾屬害蟲(Agrotis spp)、玉米穗夜蛾屬害蟲(Helicoverpa spp)、棉鈴蟲屬害蟲(Heliothis spp)等)、半翅目害蟲(例如,桃蚜、棉蚜、Aphis fabae、玉米蚜蟲、豌豆蚜、馬鈴薯蚜、小豆蚜蟲、鬱金香根蚜、Macrosiphum avenae、Methopolophium dirhodum、稻麥蚜、麥二叉蚜、菜蚜、偽菜蚜、梨綠蚜蟲、紅蘋果蚜、蘋果綿蚜、小橘蚜、大橘黑蚜等之蚜蟲類(Aphididae,Adelgidae,Phylloxeridae)、黑尾葉蟬、茶小綠葉蟬等之葉蟬類、斑飛蝨、鳶色飛蝨、白背飛蝨等之飛蝨類、白星椿象、南方綠椿象、紅鬚細綠蝽等之椿象類、銀葉粉蝨、煙草粉蝨、溫室粉蝨等之粉蝨類(Aleyrodidae)、康氏粉介殼蟲、柑橘粉介殼蟲、桑白介殼蟲、紅圓介殼蟲等之介殼蟲類(Diaspididae,Margarodidae,Ortheziidae,Aclerdiae,Dactylopiidae,Kerridae,Pseudococcidae,Coccidae,Eriococcidae,Asterolecaniidae,Beesonidae,Lecanodiaspididae,Cerococcidae等)、鞘翅目害蟲(例如,水稻水象鼻蟲、豆象、大黃粉蟲、西方玉米根蟲、南方玉米根蟲、赤腳銅金龜、紅銅麗金龜、黃條葉蚤、瓜葉蟲、科羅拉多金花蟲、稻負泥蟲、食芯蟲類、天牛類等)、壁蝨目(例如,二點葉蟎、神澤葉蟎、柑橘葉蟎等)、膜翅目害蟲(例如廣腰亞目)、直翅目害蟲(例
如,蝗蟲類)、雙翅目害蟲(例如,潛葉蠅類)、薊馬目害蟲(例如,南黃薊馬、柑橘黃薊馬等)、植物寄生性線蟲(例如,根瘤線蟲、根腐線蟲、稻芯枯線蟲、松材線蟲等)等,動物的寄生蟲方面,可舉出血蜱類(例如,孤星美洲血蜱、墨西哥灣岸血蜱、牛血蜱、落磯山脈森林血蜱、西海岸血蜱、美洲犬蜱、何氏血蜱、褐黃血蜱、長角血蜱、巨棘血蜱、篦麻硬蜱、卵形硬蜱、西部黑腳壁蝨、全溝血蜱、綿羊硬蜱、黑腳壁蝨、鳥壁蝨、鐮形扇隻蜱)、爪蟎類(例如,貓爪蟎、犬爪蟎)、毛囊蟎類(例如,犬毛囊蟎、貓毛囊蟎)、慅蟎類(例如,牛慅蟎)、疥癬蟎類(例如,牛食皮疥癬蟎、犬耳疥癬蟎)、禽刺蟎類(例如,鳥刺蟎)、雞皮刺蟎類、羽蟎類(例如,雞羽蟎、鈍翅蟎)、恙蟲類(例如,宮川恙蟲、赤恙蟲)、蚤類(例如,貓蚤、人蚤、印度鼠蚤、鼠蚤)、羽蝨類(例如,犬羽蝨、雞羽蝨)、虱類(例如,豬虱、犬虱、隻虱、人虱、毛虱、床虱)、蠅類(例如,家蠅類、牛蠅類、刺蠅類、馬蠅類)、蝶蠅類(例如,白蛉)、采采蠅、虻類、斑蚊類(例如,白線斑蚊、熱帶斑蚊)、赤家蚊類(例如,赤家蚊)、瘧蚊類、糠蚊類等)、蚋類、糠蚊類、刺椿象類、小黃家蟻、線蟲類(例如,糞線蟲類、鈎蟲類、圓蟲類(例如,捻轉胃蟲、鼠圓蟲)、毛樣線蟲類、變圓蟲類(例如,豚肺蟲、廣東住血線蟲、貓肺蟲)、蟯蟲類、盲腸蟲類(例如,雞蛔蟲)、蛔蟲類(例如,胃黏膜蛔蟲、豚蛔蟲、馬蛔蟲、犬蛔蟲、貓蛔蟲)、
旋尾線蟲類(例如,錐尾科類、有棘顎口蟲、貓胃蟲、類圓豚胃蟲、大口馬胃蟲、雞胃蟲麥金那蟲)、絲狀蟲類(例如,犬絲狀蟲、淋巴系絲狀蟲、回旋絲狀蟲、螺絲狀蟲)、腎蟲類、旋毛蟲類(例如,犬鞭蟲、旋毛蟲))、吸蟲類(例如,日本住血吸蟲、肝蛭)、鉤隻蟲類、條蟲類(例如,疑葉類(例如,曼氏裂隻條蟲)、圓葉類(例如,瓜實條蟲))、原蟲類等等,衛生害蟲方面,可舉出蜚蠊類(例如,德國蜚蠊)、粉壁蝨類(例如,長毛粉壁蝨),甚至是白蟻類(例如,住家白蟻)。此等之中,施用本發明之有害生物防治劑的蟲種,較佳的有鱗翅目害蟲、半翅目害蟲、薊馬目害蟲、雙翅目害蟲、鞘翅目害蟲、動物寄生性之蚤類或壁蝨類、犬絲狀蟲、蜚蠊類、白蟻類(例如,小菜蛾、斜紋夜盗蛾、棉蚜、桃蚜、斑飛蝨、鳶色飛蝨、白背飛蝨、黑尾葉蟬、柑橘黃薊馬、瓜葉蟲、稻負泥蟲、水稻水象鼻蟲、紅鬚細綠蝽、家蠅、長角血蜱、犬絲條蟲、德國蜚蠊、及、住家白蟻所成之群選出的至少1個蟲種),特佳為、小菜蛾、棉蚜、桃蚜、斑飛蝨、鳶色飛蝨、白背飛蝨、黑尾葉蟬、瓜葉蟲、稻負泥蟲、水稻水象鼻蟲、紅鬚細綠蝽、家蠅、長角血蜱。
本說明書中,可於式(I)所示之新穎亞胺基吡啶衍生物中混合的其他有害生物防治劑方面,可舉出殺蟲劑、殺菌劑、殺壁蝨劑、除草劑、植物成長調節劑、動物寄生蟲防治劑,具體的藥劑方面,可舉例如農藥手冊(The Pesticide Manual、第13版The British Crop Protection
Council發行)及SHIBUYA INDEX(第15版、2010年、SHIBUYA INDEX RESEARCH GROUP發行)中所記載的。
可於式(I)所示之新穎亞胺基吡啶衍生物中混合的其他有害生物防治劑方面,較佳可舉出殺蟲劑、殺菌劑、除草劑、動物寄生性害蟲防治劑,亦可舉出殺蟲劑中進一步混合殺菌劑者。
可於式(I)所示之新穎亞胺基吡啶衍生物中混合的其他有害生物防治劑之較佳之例方面,殺蟲劑可舉出有機磷酸酯系化合物、胺基甲酸酯系化合物、沙蠶毒素衍生物、有機氯系化合物、除蟲菊酯系化合物、苯甲醯基尿素系化合物、保幼激素樣化合物、脫皮激素樣化合物、新菸鹼系化合物、神經細胞的鈉通道阻滯劑、殺蟲性大環狀內酯、γ-胺基酪酸(GABA)拮抗劑、萊恩素受體(ryanodine receptors)作用性化合物、殺蟲性尿素類、BT劑、昆蟲病原病毒劑等,更佳的具體例方面,可舉出包含歐殺松(acephate)、二氯松(dichlorvos)、EPN、撲滅松(fenitrothion)、芬滅松(fenamifos)、普硫松(prothiofos)、佈飛松(profenofos)、白克松(pyraclofos)、甲基毒死蜱(chlorpyrifos-methyl)、大利松(diazinon)、三氯松(trichlorfon)、四氯乙烯磷(tetrachlorvinphos)、溴酚磷(bromofenofos)、賽硫磷(cythioate)之有機磷酸酯系化合物、包含納乃得(methomy1)、硫敵克(thiodicarb)、得滅克
(aldicarb)、毆殺滅(oxamyl)、安丹(propoxur)、加保利(carbaryl)、丁基滅必蝨(fenobucarb)、乙硫甲威(ethiofencarb)、芬硫克(fenothiocarb)、比加普(pirimicarb)、加保扶(carbofuran)、免扶克(benfuracarb)之胺基甲酸酯系化合物、包含培丹(cartap)、硫賜安(thiocyclam)之沙蠶毒素衍生物、包含大克蟎(dicofol)、得脫蟎(tetradifon)之有機氯系化合物、包含丙烯菊酯(allethrin)、d.d-T-丙烯菊酯(d.d-T-allethrin)、dl.d-T80丙烯菊酯(dl.d-T80 allethrin)、除蟲菊酯(pyrethrins)、苯醚菊酯(phenothrin)、氟氯苯菊酯(flumethrin)、氟氯氰菊酯(cyfluthrin)、d.d-T80丙炔菊酯(d.d-T80 prarethrin)、胺菊酯(phthalthrin)、四氟苯菊酯(transfluthrin)、苄呋菊酯(resmethrin)、苯醚氰菊酯(cyphenothrin)、除蟲菊萃取物(pyrethrum extract)、協力靈222(synepirin222)、協力靈500(synepirin 500)、百滅寧(permethrin)、七氟菊酯(tefluthrin)、賽滅寧(cypermethrin)、第滅寧(deltamethrin)、賽洛寧(cyhalothrin)、芬化利(fenvalerate)、福化利(fluvalinate)、依芬寧(ethofenprox)、矽護芬(silafluofen)之除蟲菊酯系化合物、包含二福隆(diflubenzuron)、得福隆(teflubenzuron)、氟芬隆(flufenoxuron)、克福隆(chlorfluazuron)、祿芬隆(lufenuron)之苯甲醯基尿素系化合物、包含烯蟲丙酯
(methoprene)之保幼激素樣化合物、包含可芬諾之脫皮激素樣化合物。再者,其他化合物方面,可舉出布芬淨(buprofezin)、合賽多(hexythiazox)、三亞蟎(amitraz)、克死蟎(chlordimeform)、畢達本(pyridaben)、芬普蟎(fenpyroxymate)、畢汰芬(pyrimidifen)、得芬瑞(tebufenpyrad)、脫芬瑞(tolfenpyrad)、亞醌蟎(acequinocyl)、賽芬蟎(cyflumetofen)、氟大滅(flubendizmide)、益斯普(ethiprole)、芬普尼(fipronil)、乙蟎唑(etoxazole)、益達胺(imidacloprid)、可尼丁(clothianidin)、賽速安(thiamethoxam)、亞滅培(acetamiprid)、烯啶蟲胺(nitenpyram)、賽果培(thiacloprid)、達特南(dinotefuran)、派滅淨(pymetrozine)、必芬蟎(bifenazate)、賜派芬(spirodiclofen)、螺甲蟎酯(spiromesifen)、賜派滅(spirotetramat)、氟尼胺(flonicamid)、克凡派(chlorfenapyr)、百利普芬(pyriproxyfen)、因得克(indoxacarb)、三氟甲吡醚(pyridalyl)、賜諾殺(spinosad)、賜諾特(spinetoram)、阿巴汀(avermectin)、倍脈心(milbemycin)、吡唑殺蟎(pyflubumide)、賽必芬蟎(cyenopyrafen)、百利氟松(pyrifluquinazon)、剋安勃(chlorantraniliprole)、氰蟲醯胺(cyantraniliprole)、雷皮菌素(lepimectin)、美氟綜(metaflumizone)、必拉氟勃(pyrafluprole)、必
利勃(pyriprole)、愛美松(hydramethylnon)、唑蚜威(triazamate)、氟啶蟲胺腈(sulfoxaflor)、氟比拉二福隆(flupyradifurone)、氟奎因(flometoquin)、害獲滅(ivermectin)、司拉克丁(selamectin)、莫昔克丁(moxidectin)、多拉克丁(doramectin)、依普立諾克丁(eprinomectin)、倍脈心肟(milbemycin oxime)、避蚊胺(deet)、噁蟲酮(metoxadiazone)、賽滅淨(cyromazine)、氟幼靈(triflumuron)、大茴香油(star anise oil)、三氯苯達唑(triclabendazole)、氟苯達唑(flubendazole)、芬苯達唑(fenbendazole)、葡萄糖酸銻鈉(antimony sodium gluconate)、鹽酸左旋咪唑(levamisole hydrochloride)、雙硫酸醇(bithionol)、二氯酚(dichlorophen)、酚噻嗪(phenothiazine)、二硫化碳哌嗪(piperazine carbon disulfide)、磷酸哌嗪(piperazine phosphate)、己二酸哌嗪(piperazine adipate)、檸檬酸哌嗪(piperazine citrate)、美拉索明二鹽酸鹽(melarsomine dihydrochloride)、美替立啶(metyridine)、茴蒿素(santonin)、羥萘酸吡喃泰(pyrantel pamoate)、吡喃泰(pyrantel)、帕芝奎(praziquantel)、苯硫胍(febantel)、艾默德斯(emodepside)、因滅汀安息香酸鹽(emamectin benzoate)、環氧蟲啶(Cycloxaprid)、1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido〔1,2-a〕pyrimidin-1-ium-2-olate、有機金屬系化合物、
二硝基系化合物、有機硫化合物、尿素系化合物、三嗪系化合物、聯胺系化合物、及次式(II)所示之化合物、或該等之農畜藥上可容許之酸加成鹽。該等之酸加成鹽方面,可舉出鹽酸鹽、硝酸鹽、硫酸鹽、磷酸鹽、或醋酸鹽等。
〔式中,Het1表示3-吡啶基、R1表示羥基、R2、R3表示環丙基羰基氧基、R4表示羥基〕
可於式(I)所示之新穎亞胺基吡啶衍生物中混合的其他殺蟲劑之更佳的例方面,可舉出亞滅培(acetamiprid)、益達胺(imidacloprid)、烯啶蟲胺(nitenpyram)、可尼丁(clothianidin)、亞滅培(acetamiprid)、達特南(dinotefuran)、賽果培(thiacloprid)、賽速安(thiamethoxam)、派滅淨(pymetrozine)、賜諾殺(spinosad)、賜諾特(spinetram)、芬普尼(fipronil)、剋安勃(chloranthraniliprole)、氰蟲醯胺(cyantraniliprole)、
培丹(cartap)、硫賜安(thiocyclam)、免扶克(benfuracarb)、布芬淨(buprofezin)、依芬寧(ethofenprox)、矽護芬(silafluofen)、益斯普(ethiprole)、氟尼胺(flonicamid)、氟啶蟲胺腈(sulfoxaflor)、氟比拉二福隆(flupyradifurone)、氟奎因(flometoquin)、因滅汀安息香酸鹽(emamectin benzoate)、環氧蟲啶(Cycloxaprid)、1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido〔1,2-a〕pyrimidin-1-ium-2-olate、及阿啡多片(afidopyropen)、前述式(II)所示之化合物、或該等之農畜藥上可容許之酸加成鹽。再者,特佳之例方面,可舉出百滅寧(permethrin)、亞滅培(acetamiprid)、益達胺(imidacloprid)、可尼丁(clothianidin)、達特南(dinotefuran)、賽果培(thiacloprid)、賽速安(thiamethoxam)、派滅淨(pymetrozine)、賜諾殺(spinosad)、賜諾特(spinetram)、芬普尼(fipronil)、剋安勃(chloranthraniliprole)、氰蟲醯胺(cyantraniliprole)、三亞蟎(amitraz)、依芬寧(ethofenprox)、矽護芬(silafluofen)、益斯普(ethiprole)、氟尼胺(flonicamid)、氟啶蟲胺腈(sulfoxaflor)、氟比拉二福隆(flupyradifurone)、氟奎因(flometoquin)、害獲滅(ivermectin)、莫昔克丁(moxidectin)、因滅汀安息香酸鹽(emamectin benzoate)、環氧蟲啶(cycloxaprid)、1-((6-
chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido〔1,2-a〕pyrimidin-1-ium-2-olate、及阿啡多片(afidopyropen)、或該等之農畜藥上可容許之酸加成鹽。
式(I)所示之新穎亞胺基吡啶衍生物亦可與BT劑、昆蟲病原病毒劑等之微生物農藥混用或併用。
可於式(I)所示之新穎亞胺基吡啶衍生物中混合的殺菌劑之例方面,可舉例如包含亞托敏(azoxystrobin)、肟醚菌胺(orysastrobin)、克收欣(kresoxym-methyl)、三氟敏(trifloxystrobin)等之甲氧丙烯酸酯系化合物、滅派林(mepanipyrim)、派美尼(pyrimethanil)、賽普洛(cyprodinil)之苯胺嘧啶系化合物、包含三泰芬(triadimefon)、比多農(bitertanol)、三氟菌唑(triflumizole)、乙環唑(etaconazole)、普克利(propiconazole)、平克唑(penconazole)、護矽得(flusilazole)、腈菌唑(myclobutanil)、環唑醇(cyproconazole)、戊唑醇(tebuconazole)、菲克利(hexaconazole)、撲克拉(prochloraz)、矽氟唑(simeconazole)之唑系化合物、包含滅蟎猛(quinomethionate)之喹喔啉系化合物、包含代森錳(maneb)、代森鋅(zineb)、代森錳鋅(mancozeb)、聚胺基甲酸酯(polycarbamate)、丙森鋅(propineb)之二硫代胺基甲酸酯系化合物、包含乙霉威(diethofencarb)之苯基胺基甲酸酯系化合物、包含四氯
異苯腈(chlorothalonil)、五氯硝基苯(quintozene)之有機氯系化合物、包含免賴得(benomyl)、甲基多保淨(thiophanate-methyl)、卡苯達唑(carbendazole)之苯咪唑系化合物、包含滅達樂(metalaxyl)、毆殺斯(oxadixyl)、歐呋醯胺(ofurase)、本達樂(benalaxyl)、呋霜靈(furalaxyl)、酯菌胺(cyprofuram)之苯基醯胺系化合物、包含苯氟磺胺(dichlofluanid)之次磺酸系化合物、包含氫氧化銅(II)(copper hydroxide)、羥基喹啉銅(oxine-copper)之銅系化合物、包含羥基異噁唑(hydroxyisoxazole)之異噁唑系化合物、包含三乙膦酸鋁(fosetyl-aluminium)、甲基立枯磷(tolclofos-methyl)之有機磷系化合物、包含卡丹(captan)、四氯丹(captafol)、滅菌丹(folpet)之N-鹵基硫代烷基系化合物、包含撲滅寧(procymidone)、依普同(iprodione)、免克寧(vinchlozolin)之二羧基醯亞胺系化合物、包含賽氟滅粒劑(thifluzamide)、福拉比(furametpyr)、福多寧(flutolanil)、滅普寧(mepronil)之苯甲醯苯胺系化合物、包含芬普福(fenpropimorph)、達滅芬(dimethomorph)之嗎啉系化合物、包含氫氧化三苯基錫(fenthin hydroxide)、醋酸三苯基錫(fenthin acetate)之有機錫系化合物、包含護汰寧(fludioxonil)、拌種咯(fenpiclonil)之氰基吡咯系化合物、包含苯并噻二唑S甲基(acibenzolar-S-
methyl)、異噻菌胺(isotianil)、噻醯菌胺(tiadinil)、加普胺(carpropamid)、雙氯氰菌胺(diclocymet)、芬諾尼(fenoxanil)、三賽唑(tricyclazole)、百快隆(pyroquilon)、富米綜(ferimzone)、熱必斯(fthalide)、扶吉胺(fluazinam)、克絕(cymoxanil)、賽福寧(triforine)、比芬諾(pyrifenox)、烯丙苯噻唑(probenazole)、芬瑞莫(fenarimol)、苯鏽啶(fenpropidin)、戊菌隆(pencycuron)、賽座滅(cyazofamid)、異丙菌胺(iprovalicarb)、替伏素(tebufloquin)、異丙基苯噻菌胺(benthiavalicarb-isopropyl)、脫普洛卡(tolprocarb)、維利黴素(validamycin)、春雷黴素(Kasugamycin)、鏈黴素(Streptomycin)、UK-2A類之9員環二內酯化合物、次式(III)所示之特開2009-078991記載之化合物、次式(IV)所示之再公表WO08/066148記載之化合物、及次式(V)所示之再公表WO09/028280記載之化合物、或該等之農畜藥上可容許之酸加成鹽。
〔式中,R1及R2表示氫原子或碳數1~6之鹵烷基等(惟,R1及R2的至少1個表示碳數1~6之鹵烷
基)、R3表示氫原子等、A表示OR4、SR5、NR6R7或NR8NR9R10、R4表示碳數8~12之烷基等、R5表示碳數1~12之烷基等、R6及R7表示氫原子或碳數8~12之烷基等、R8、R9及R10表示氫原子或碳數1~12之烷基等〕
〔式中,R1、R2表示C1~C6烷基、芳基、雜芳基、芳烷基、R3、R4表示氫原子、C1~C6烷基、鹵素原子、C1~C6烷氧基、X表示鹵素原子、C1~C6烷基、C2~C6烯基、C2~C6炔基、芳基、雜芳基、C1~C6烷氧基、Y表示鹵素原子、C1~C6烷基、C1~C6烷氧基、羥基、n表示0~4、m表示0~6〕。
〔式中,R1表示烷基等、R2及R3各自獨立地表示氫原子、鹵烷基等(惟,R2及R3的至少1個為碳數1~6之鹵烷基)。A表示-OR4、-SR5、-NR6R7或-NR8NR9R10、R4表示碳數3~12之烷基等、R5表示碳數
1~12之烷基等、R6表示氫原子等、R7表示碳數5~12之烷基等、R8、R9及R10表示碳數1~12之烷基等〕
可於式(I)所示之新穎亞胺基吡啶衍生物中混合的其他殺菌劑之更佳的例方面,可舉出亞托敏(azoxystrobin)、肟醚菌胺(orysastrobin)、賽氟滅粒劑(thifluzamide)、福拉比(furametpyr)、熱必斯(fthalide)、烯丙苯噻唑(probenazole)、苯并噻二唑S甲基(acibenzolar-S-methyl)、噻醯菌胺(tiadinil)、異噻菌胺(isotianil)、加普胺(carpropamid)、雙氯氰菌胺(diclocymet)、芬諾尼(fenoxanil)、三賽唑(tricyclazole)、百快隆(pyroquilon)、富米綜(ferimzone)、替伏素(tebufloquin)、矽氟唑(simeconazole)、維利黴素(validamycin)、春雷黴素(Kasugamycin)、戊菌隆(pencycuron),再特佳之例方面,可舉出烯丙苯噻唑(probenazole)、替伏素(tebufloquin)。
可於式(I)所示之新穎亞胺基吡啶衍生物中混合的其他有害生物防治劑之較佳之例方面,除草劑可舉出脂質合成阻礙劑、乙醯乳酸合成阻礙劑、光合成阻礙劑、原卟啉原氧化酶Ⅸ氧化阻礙劑、白化除草劑、胺基酸合成阻礙劑、二氫蝶酸合成酵素阻礙劑、細胞分裂阻礙劑、超長鏈脂肪酸合成阻礙劑、纖維素生合成阻礙劑、去共軛劑、生長素樣除草劑、生長素輸送阻礙劑等。具體而言,可舉出亞汰草(alloxydim)、亞汰草鈉(alloxydim-sodium)、
丁苯草酮(butroxydim)、剋草同(clethodim)、炔草酸(clodinafop)、丙炔草酯(clodinafop-propargyl)、噻草酮(cycloxydim)、賽伏草(cyhalofop)、丁基賽伏草(cyhalofop-butyl)、禾草靈(diclofop)、甲基禾草靈(diclofop-methyl)、芬殺草(fenoxaprop)、乙基芬殺草(fenoxaprop-ethyl)、芬殺草-P(fenoxaprop-P)、乙基芬殺草-P(fenoxaprop-P-ethyl)、吡氟禾草靈(fluazifop)、丁基吡氟禾草靈(fluazifop-butyl)、精吡氟禾草靈(fluazifop-P)、丁基精吡氟禾草靈(fluazifop-P-butyl)、氯氟乙禾靈(haloxyfop)、甲基氯氟乙禾靈-P(haloxyfop-methyl)、氯氟乙禾靈-P(haloxyfop-P)、甲基氯氟乙禾靈-P酯(haloxyfop-P-methylester)、噁唑醯草胺(metamifop)、唑啉草酯(pinoxaden)、氯苯噻草酮(profoxydim)、喔草酯(propaquizafop)、喹禾靈(quizalofop)、乙基喹禾靈(quizalofop-ethyl)、喹禾靈四氫糠基酯(quizalofop-tefuryl)、喹禾靈-P(quizalofop-P)、乙基喹禾靈-P(quizalofop-P-ethyl)、喹禾靈-P-四氫糠基酯(quizalofop-P-tefuryl)、稀禾定(sethoxydim)、吡喃草酮(tepraloxydim)、肟草酮(tralkoxydim)、呋草黃(benfuresate)、丁酸酯(butylate)、環草特(cycloate)、達拉朋(dalapon)、哌草丹(dimepiperate)、乙基二丙基硫胺甲酸酯(S-ethyl dipropylthiocarbamat:EPTC)、戊草丹(esprocarb)、乙呋草黃(ethofumesate)、氟丙酸鹽
(flupropanate)、草達滅(molinate)、坪草丹(orbencarb)、克草猛(pebulate)、苄草丹(prosulfocarb)、三氯醋酸(trichloroacetic acid:TCA)、禾草丹(thiobencarb)、仲草丹(tiocarbazil)、野麥畏(triallate)、滅草猛(vernolate)、磺醯基尿素(sulfonylureas):醯嘧磺隆(amidosulfuron)、四唑嘧磺隆(azimsulfuron)、苄嘧磺隆(bensulfuron)、甲基苄嘧磺隆(bensulfuron-methyl)、氯嘧磺隆(chlorimuron)、乙基氯嘧磺隆(chlorimuron-ethyl)、氯磺隆(chlorsulfuron)、醚磺隆(cinosulfuron)、環磺隆(cyclosulfamuron)、胺苯磺隆(ethametsulfuron)、胺苯磺隆甲基鹽(ethametsulfuron-methyl)、乙氧嘧磺隆(ethoxysulfuron)、嘧啶磺隆(flazasulfuron)、氟吡磺隆(flucetosulfuron)、氟啶嘧磺隆(flupyrsulfuron)、氟啶嘧磺隆甲基鈉(flupyrsulfuron-methyl-sodium)、甲醯胺磺隆(foramsulfuron)、氯吡嘧磺隆(halosulfuron)、氯吡嘧磺隆甲基鹽(halosulfuron-methyl)、唑吡嘧磺隆(imazosulfuron)、碘磺隆(iodosulfuron)、碘磺隆甲基鈉(iodosulfuron-methylsodium)、甲磺胺磺隆(mesosulfuron)、嗪吡嘧磺隆(metazosulfuron)、甲磺隆(metsulfuron)、甲磺隆甲基鹽(metsulfuron-methyl)、煙嘧磺隆(nicosulfuron)、嘧苯胺磺隆(orthosulfamuron)、環氧嘧磺隆(oxasulfuron)、氟嘧
磺隆(primisulfuron)、氟嘧磺隆甲基鹽(primisulfuron-methyl)、嗪咪唑嘧磺隆(propyrisulfuron)、氟磺隆(prosulfuron)、吡嘧磺隆(pyrazosulfuron)、吡嘧磺隆乙基鹽(pyrazosulfuron-ethyl)、玉嘧磺隆(rimsulfuron)、甲嘧磺隆(sulfometuron)、甲嘧磺隆甲基鹽(sulfometuron-methyl)、磺醯磺隆(sulfosulfuron)、噻磺隆(thifensulfuron)、噻磺隆甲基鹽(thifensulfuron-methyl)、醚苯磺隆(triasulfuron)、苯磺隆(tribenuron)、苯磺隆甲基鹽(tribenuron-methyl)、三氟啶磺隆(trifloxysulfuron)、氟胺磺隆(triflusulfuron)、氟胺磺隆甲基(triflusulfuron-methyl)、三氟甲磺隆(tritosulfuron)、咪草酸(imazamethabenz)、咪草酸甲基酯(imazamethabenz-methyl)、甲氧咪草煙(imazamox)、甲咪唑煙酸(imazapic)、咪唑煙酸(imazapyr)、咪唑喹啉酸(imazaquin)、咪草煙(imazethapyr)、三唑并嘧啶系除草劑(triazolopyrimidine herbicides):氯酯磺草胺(cloransulam)、氯酯磺草胺甲基鹽(cloransulam-methyl)、雙氯磺草胺(diclosulam)、唑嘧磺草胺(flumetsulam)、雙氟磺草胺(florasulam)、磺草唑胺(metosulam)、五氟磺草胺(penoxsulam)、嘧啶硫泛(pyrimisulfan)、啶磺草胺(pyroxsulam)、雙草醚(bispyribac)、雙草醚鈉(bispyribac-sodium)、嘧啶肟
草醚(pyribenzoxim)、環酯草醚(pyriftalid)、嘧草醚(pyriminobac)、嘧草醚甲基鹽(pyriminobac-methyl)、嘧草硫醚(pyrithiobac)、嘧草硫醚鈉(pyrithiobac-sodium)、氟唑磺隆(flucarbazone)、氟唑磺隆鈉(flucarbazone-sodium)、丙苯磺隆(propoxycarbazone)、丙苯磺隆鈉(propoxycarbazone-sodium)、噻酮磺隆(thiencarbazone)、噻酮磺隆甲基(thiencarbazone-methyl)、三嗪系除草劑(triazine herbicides):氯三嗪(chlorotriazine)、三嗪酮(triazinones)、三嗪二酮(triazindiones)、甲硫基三嗪(methylthiotriazines)、噠嗪酮(pyridazinones)(例如,草殺淨(ametryn)、草脫淨(atrazine)、氯草敏(chloridazone)、氰草津(cyanazine)、敵草淨(desmetryn)、異戊乙淨(dimethametryn)、環嗪酮(hexazinone)、嗪草酮(metribuzin)、扑草通(prometon)、扑草净(prometryn)、扑滅津(propazin)、西瑪津(simazin)、西瑪津(simetryn)、特丁通(terbumeton)、特丁津(terbuthylazin)、特丁淨(terbutryn)、草達津(trietazin))、烯丙基尿素系(aryl ureas)(例如,氯溴隆(chlorobromuron)、氯麥隆(chlorotoluron)、枯草隆(chloroxuron)、噁唑隆(dimefuron)、敵草隆(diuron)、伏草隆(fluometuron)、異丙隆(isoproturon)、愛速隆(isouron)、利谷隆
(linuron)、苯嗪草酮(metamitron)、甲基苯噻隆(methabenzthiazuron)、甲氧苯草隆(metobenzuron)、甲氧隆(metoxuron)、綠谷隆(monolinuron)、草不隆(neburon)、環草隆(siduron)、特丁噻草隆(tebuthiuron)、噻苯隆(thiadiazuron))、苯基胺甲酸酯系(phenyl carbamates)(例如,甜菜安(desmedipham)、特安靈(karbutilate)、甜菜寧(phenmedipham)、甜菜寧乙基(phenmedipham-ethyl))、腈系除草劑(nitrile herbicides)(例如,溴酚肟(bromofenoxim)、溴苯腈(bromoxynil)或其鹽及酯、碘苯腈(ioxynil)或其鹽及酯)、尿嘧啶系(uraciles)(例如,除草定(bromacil)、環草定(lenacil)、特草定(terbacil))、本達隆(bentazon)、本達隆鈉(bentazon-sodium)、必汰草(pyridate)、必汰福(pyridafol)、甲氯醯草胺(pentanochlor)、除草靈(propanil)、光合成阻礙系(photosynthesis inhibtors)(例如,敵草快(diquat)、敵草快二溴化物(diquat-dibromide)、對草快(paraquat)、對草快二氯化物(paraquatdichloride)、對草快二甲基硫酸酯(paraquat-dimethylsulfate)、亞喜芬(acifluorfen)、亞喜芬鈉(acifluorfen-sodium)、草芬定(azafenidin)、苯卡巴胂(bencarbazone)、雙苯嘧草酮(benzfendizone)、甲酯除草醚(bifenox)、氟丙嘧草酯(butafenacil)、唑草酮(carfentrazone)、唑草酮
乙基酯(carfentrazone-ethyl)、甲氧基護谷(chlomethoxyfen)、吲哚酮草酯(cinidon-ethyl)、異丙吡草酯(fluazolate)、氟噠嗪草酯(flufenpyr)、氟噠嗪草酯乙基(flufenpyr-ethyl)、氟烯草酸(flumiclorac)、氟胺草酯(flumiclorac-Pentyl)、丙炔氟草胺(flumioxazin)、乙羧氟草醚(fluoroglycofen)、乙羧氟草醚乙基酯(fluoroglycofen-ethyl)、氟噻草酯(fluthiacet)、氟噻甲草酯(fluthiacet-methyl)、氟磺胺草醚(fomesafen)、鹵殺芬(halosafen)、乳氟禾草靈(lactofen)、丙炔噁草酮(oxadiargyl)、噁草酮(oxadiazon)、乙氧氟草醚(oxyfluorfen)、環戊噁草酮(pentoxazone)、氟唑草胺(profluazol)、雙唑草腈(pyraclonil)、吡草醚(pyraflufen)、吡草醚乙基酯(pyraflufen-ethyl)、苯嘧磺草胺(saflufenacil)、甲磺草胺(sulfentrazone)、噻二唑草胺(thidiazimin)、氟丁醯草胺(beflubutamid)、吡氟醯草胺(diflufenican)、氟啶酮(fluridone)、氟氯啶酮(flurochloridone)、呋草酮(flurtamone)、氟草敏(norflurazon)、吡唑特(pyrazolate)、氟吡醯草胺(picolinafen)、苯草醚(aclonifen)、胺基三唑(amitrole)、異噁草松(clomazone)、伏草隆(flumeturon)、嘉磷塞(glyphosate)及其鹽,雙丙氨磷(bialaphos)、雙丙氨磷鈉(bialaphos-sodium)、草胺膦(glufosinate)、草胺膦-P(glufosinate-P)、草胺膦銨
(glufosinate-ammonium)、磺草靈(asulam)、二硝基苯胺系(dinitroanilines)(例如,氟草胺(benfluralin)、地禾胺(butralin)、敵樂胺(dinitramine)、乙丁烯氟靈(ethalfluralin)、氟消草(fluchloralin)、胺磺禾靈(oryzalin)、硝草胺(pendimethalin)、氨基丙氟靈(prodiamine)、三氟樂靈(trifluralin))、磷醯胺系除草劑(phosphoramidate herbicide)(例如,胺草磷(amiprophos)、胺草磷甲基酯(amiprophos-methyl)、抑草磷(butamifos))、安息香酸系除草劑(benzoic acid herbicides)(例如,氯酞酸(chlorthal)、氯酞酸二甲基酯(chlorthal-dimethyl))、吡啶系(pyridines)(例如,氟硫草定(dithiopyr)、噻草定(thiazopyr)、苯并醯胺系(benzamides)(例如,炔苯醯草胺(propyzamide)、牧草胺(tebutam))、氯乙醯胺系(chloroacetamides)(例如,乙草胺(acetochlor)、甲草胺(alachlor)、丁草胺(butachlor)、二甲草胺(dimethachlor)、二甲吩草胺(dimethenamid)、二甲吩草胺-P(dimethenamid-P)、滅草胺(metazachlor)、異丙甲草胺(metolachlor)、異丙甲草胺-S(metolachlor-S)、烯草胺(pethoxamid)、丙草胺(pretilachlor)、毒草胺(propachlor)、異丙草胺(propisochlor)、噻吩草胺(thenylchlor))、氧基乙醯苯胺系(oxyacetanilides)(例如,氟噻草胺(flufenacet)、苯噻醯草胺
(mefenacet))、乙醯苯胺系(acetanilides)(例如,雙苯醯草胺(diphenamid)、萘丙胺(naproanilide)、萘氧丙草胺(napropamide))、四唑啉酮系(tetrazolinones)(例如,四唑醯草胺(fentrazamide))、莎稗磷(anilofos)、唑草胺(cafenstrole)、芬諾殺草碸(fenoxasulfone)、異匍芬卡綜(ipfencarbazone)、哌草磷(piperophos)、派羅克殺草碸(pyroxasulfone))、氯硫醯草胺(chlorthiamid)、二氯苯腈(dichlobenil)、氟胺草唑(flupoxam)、異噁草胺(isoxaben)、地樂吩(dinoseb)、特樂吩(dinoterb),4,6-二硝基鄰甲酚(4,6-dinitro-o-cresol:DNOC)及其鹽,2,4-D及其鹽或酯、2,4-DB及其鹽或酯、氯氨吡啶酸(aminopyralid)及其鹽(例如,氯氨吡啶酸-參(2-羥基丙基)銨(aminopyralid-tris(2-hydroxypropyl)ammonium)及其酯、草除靈(benazolin)、草除靈乙基酯(benazolin-ethyl)、草滅平(chloramben)及其鹽或酯、克普草(clomeprop)、畢克草(clopyralid)及其鹽或酯、百草敵(dicamba)及其鹽或酯、二氯苯氧基丙酸(dichlorprop)及其鹽或酯、二氯苯氧基丙酸-P(dichlorprop-P)及其鹽或酯、氟草煙(fluroxypyr)及其鹽或酯,2-甲基-4-氯苯氧基醋酸(2-methyl-4-chlorophenoxyacetic acid:MCPA)及其鹽或酯、MCPA硫代乙基酯(MCPA-thioethyl)、4-(2-甲基-4-氯苯氧基)
酪酸(MCPB)及其鹽或酯、氯苯氧丙酸(mecoprop)及其鹽或酯、氯苯氧丙酸-P(mecoprop-P)及其鹽或酯、氨氯砒碇酸(picloram)及其鹽或酯、快克草(quinclorac)、氯甲喹啉酸(quinmerac),2,3,6-三氯安息香酸(TBA(2,3,6))及其鹽或酯、三氯比(triclopyr)及其鹽或酯、環丙嘧啶酸(aminocyclopyrachlor)及其鹽或酯、氟吡草腙(diflufenzopyr)及其鹽、奈草胺(naptalam)及其鹽、溴丁醯草胺(bromobutide)、氯芴素(chlorflurenol)、氯芴素甲基酯(chlorflurenol-methyl)、環庚草醚(cinmethylin)、苄草隆(cumyluron)、達拉朋(dalapon)、棉隆(dazomet)、雙苯唑快(difenzoquat)、雙苯唑快甲基硫酸酯(difenzoquat-methylsulfate)、噻節因(dimethipin)、甲胂二鈉(DSMA)、殺草隆(dymron)、棉脫葉劑(endothal)及其鹽、乙氧苯草胺(etobenzanid)、麥草伏(flamprop)、麥草伏異丙基酯(flamprop-isopropyl)、麥草伏甲基酯(flamprop-methyl)、麥草伏-M-異丙基酯(flamprop-M-isopropyl)、麥草伏-M-甲基酯(flamprop-M-methyl)、芴醇(flurenol)、芴醇丁基酯(flurenol-butyl)、氟嘧醇(flurprimidol)、殺木膦(fosamine)、殺木膦銨(fosamine-ammonium)、茚草酮(indanofan)、三嗪茚草胺(indaziflam)、順丁烯二醯肼(maleic hydrazide)、氟磺醯草胺(mefluidide)、美
坦(metam)、甲硫除草靈(methiozolin)、疊氮化甲基酯(methyl azide)、溴化甲基酯(methyl bromide)、甲基殺草隆(methyl-dymron)、碘化甲烷(methyl iodide)、MSMA、油酸(oleic acid)、噁嗪草酮(oxaziclomefone)、天竺葵酸(pelargonic acid)、稗草畏(pyributicarb)、滅藻醌(quinoclamine)、三嗪氟草胺(triaziflam)、滅草環(tridiphane)、6-氯-3-(2-環丙基-6-甲基苯氧基)-4-吡嗪醇(6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol:CAS 499223-49-3)及其鹽或酯。
可於式(I)所示之新穎亞胺基吡啶衍生物中混合之動物寄生性害蟲防治劑方面,可舉出有機磷酸酯系化合物、胺基甲酸酯系化合物、沙蠶毒素衍生物、有機氯系化合物、除蟲菊酯系化合物、苯甲醯基尿素系化合物、保幼激素樣化合物、脫皮激素樣化合物、新菸鹼系化合物、神經細胞的鈉通道阻滯劑、殺蟲性大環狀內酯、γ-胺基酪酸(GABA)拮抗劑、萊恩素受體(ryanodine receptors)作用性化合物、殺蟲性尿素類等。更佳的具體例方面,可舉出包含二氯松(dichlorvos)、EPN、撲滅松(fenitrothion)、芬滅松(fenamifos)、普硫松(prothiofos)、佈飛松(profenofos)、白克松(pyraclofos)、甲基毒死蜱(chlorpyrifos-methyl)、大利松(diazinon)、三氯松(trichlorfon)、四氯乙烯磷(tetrachlorvinphos)、溴酚磷(bromofenofos)、賽硫磷
(cythioate)、芬殺松(fenthion)之有機磷酸酯系化合物、包含納乃得(methomy1)、硫敵克(thiodicarb)、得滅克(aldicarb)、毆殺滅(oxamyl)、安丹(propoxur)、加保利(carbaryl)、丁基滅必蝨(fenobucarb)、乙硫甲威(ethiofencarb)、芬硫克(fenothiocarb)、比加普(pirimicarb)、加保扶(carbofuran)、免扶克(benfuracarb)之胺基甲酸酯系化合物、包含培丹(cartap)、硫賜安(thiocyclam)之沙蠶毒素衍生物、大克蟎(dicofol)、得脫蟎(tetradifon)之有機氯系化合物、包含丙烯菊酯(allethrin)、d.d-T-丙烯菊酯(d.d-T-allethrin)、dl.d-T80丙烯菊酯(dl.d-T80 allethrin)、除蟲菊酯(pyrethrins)、苯醚菊酯(phenothrin)、氟氯苯菊酯(flumethrin)、氟氯氰菊酯(cyfluthrin)、d.d-T80丙炔菊酯(d.d-T80 prarethrin)、胺菊酯(phthalthrin)、四氟苯菊酯(transfluthrin)、苄呋菊酯(resmethrin)、苯醚氰菊酯(cyphenothrin)、除蟲菊萃取物(pyrethrum extract)、協力靈222(synepirin222)協力靈500(synepirin 500)、百滅寧(permethrin)、七氟菊酯(tefluthrin)、賽滅寧(cypermethrin)、第滅寧(deltamethrin)、賽洛寧(cyhalothrin)、芬化利(fenvalerate)、福化利(fluvalinate)、依芬寧(ethofenprox)、矽護芬(silafluofen)之除蟲菊酯系化合物、包含二福隆(diflubenzuron)、得福隆(teflubenzuron)、氟芬隆
(flufenoxuron)、克福隆(chlorfluazuron)、祿芬隆(lufenuron)之苯甲醯基尿素系化合物、包含烯蟲丙酯(methoprene)之保幼激素樣化合物、包含可芬諾之脫皮激素樣化合物。再者,其他化合物方面,可舉出三亞蟎(amitraz)、克死蟎(chlordimeform)、芬普尼(fipronil)、乙蟎唑(etoxazole)、益達胺(imidacloprid)、可尼丁(clothianidin)、賽速安(thiamethoxam)、亞滅培(acetamiprid)、烯啶蟲胺(nitenpyram)、賽果培(thiacloprid)、達特南(dinotefuran)、賜派芬(spirodiclofen)、百利普芬(pyriproxyfen)、因得克(indoxacarb)、賜諾殺(spinosad)、賜諾特(spinetoram)、阿巴汀(avermectin)、倍脈心(milbemycin)、美氟綜(metaflumizone)、必拉氟勃(pyrafluprole)、必利勃(pyriprole)、愛美松(hydramethylnon)、唑蚜威(triazamate)、氟啶蟲胺腈(sulfoxaflor)、氟比拉二福隆(flupyradifurone)、害獲滅(ivermectin)、司拉克丁(selamectin)、莫昔克丁(moxidectin)、多拉克丁(doramectin)、依普立諾克丁(eprinomectin)、倍脈心肟(milbemycin oxime)、檸檬酸二乙碳醯嗪(diethylcarbamazine citrate)避蚊胺(deet)、噁蟲酮(metoxadiazone)、賽滅淨(cyromazine)、氟幼靈(triflumuron)、大茴香油(star anise oil)、三氯苯達唑(triclabendazole)、氟苯達唑(flubendazole)、芬苯
達唑(fenbendazole)、葡萄糖酸銻鈉(antimony sodium gluconate)、鹽酸左旋咪唑(levamisole hydrochloride)、雙硫酸醇(bithionol)、二氯酚(dichlorophen)、酚噻嗪(phenothiazine)、二硫化碳哌嗪(piperazine carbon disulfide)、磷酸哌嗪(piperazine phosphate)、己二酸哌嗪(piperazine adipate)、檸檬酸哌嗪(piperazine citrate)、美拉索明二鹽酸鹽(melarsomine dihydrochloride)、美替立啶(metyridine)、茴蒿素(santonin)、羥萘酸吡喃泰(pyrantel pamoate)、吡喃泰(pyrantel)、帕芝奎(praziquantel)、苯硫胍(febantel)、艾默德斯(emodepside)、得曲恩特(derquantel)、蒙內龐特(monepantel)、因滅汀安息香酸鹽(emamectin benzoate)、環氧蟲啶(Cycloxaprid)、及次式(VI)所示之化合物、或該等之農畜藥上可容許之酸加成鹽。該等之酸加成鹽方面,可舉出鹽酸鹽、硝酸鹽、硫酸鹽、磷酸鹽、或醋酸鹽等。
更佳的例方面,可舉出氟氯苯菊酯(flumethrin)、百滅寧(permethrin)、芬普尼(fipronil)、必利勃(pyriprole)、益達胺(imidacloprid)、賽速安(thiamethoxam)、亞滅培(acetamiprid)、達特南(dinotefuran)、三亞蟎(amitraz)、美氟綜(metaflumizon)、百利普芬(pyriproxyfen)、撲滅松(fenitrothion)、祿芬隆(lufenuron)、乙蟎唑
(ethoxazole)、賜諾殺(spinosad)、賜諾特(spinetoram)、艾默德斯(emodepside)、因滅汀安息香酸鹽、害獲滅(ivermectin)、司拉克丁(selamectin)、莫昔克丁(moxidectin)、多拉克丁(doramectin)、依普立諾克丁(eprinomectin)、得曲恩特(derquantel)、蒙內龐特(monepantel)等。
本發明中,特佳之例方面,有害生物防治用組成物為農園藝用有害生物防治劑時,式(I)所示之新穎亞胺基吡啶衍生物係選自N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙醯胺(化合物P212)、N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙硫醯胺(化合物1-20)或N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟-N’-異丙基乙脒(化合物1-45)之1種以上的化合物,其他有害生物防治劑係含有1種以上選自亞滅培(acetamiprid)、益達胺(imidacloprid)、可尼丁(clothianidin)、達特南(dinotefuran)、賽果培(thiacloprid)、芬普尼(fipronil)、賽速安(thiamethoxam)、派滅淨(pymetrozine)、氟尼胺(flonicamid)、賜諾殺(spinosad)、氰蟲醯胺(cyantraniliprole)、剋安勃(chlorantraniliprole)、依芬寧(ethofenprox)、矽護芬(silafluofen)、益斯普(ethiprole)、氟啶蟲胺腈(sulfoxaflor)、氟比拉二福隆(flupyradifurone)、氟奎因(flometoquin)、因滅汀安息香酸鹽(emamectin
benzoate)、環氧蟲啶(cycloxaprid)、1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido〔1,2-a〕pyrimidin-1-ium-2-olate、及阿啡多片(afidopyropen)、肟醚菌胺(orysastrobin)、賽氟滅粒劑(thifluzamide)、福拉比(furametpyr)、熱必斯(fthalide)、烯丙苯噻唑(probenazole)、苯并噻二唑S甲基酯(acibenzolar-S-methyl)、噻醯菌胺(tiadinil)、異噻菌胺(isotianil)、加普胺(carpropamid)、雙氯氰菌胺(diclocymet)、芬諾尼(fenoxanil)、三賽唑(tricyclazole)、百快隆(pyroquilon)、富米綜(ferimzone)、替伏素(tebufloquin)、亞托敏(azoxystrobin)、矽氟唑(simeconazole)、維利黴素(validamycin)、賽氟滅粒劑(thifluzamide)、福拉比(furametpyr)、戊菌隆(pencycuron)之殺蟲劑或殺菌劑所成的有害生物防治用組成物。
本發明之有害生物防治用組成物,除了式(I)所示之新穎亞胺基吡啶衍生物、其他的殺蟲劑、殺菌劑、除草劑、動物寄生蟲防治劑之外,亦可使用農畜藥上可容許之擔體(固體擔體、液體擔體、氣體狀擔體、界面活性劑、分散劑等其他製劑用補助劑)來調製。
本發明之有害生物防治用組成物為農園藝用有害生物防治劑時,通常可與農園藝上可容許之擔體(固體擔體、
液體擔體、氣體狀擔體、界面活性劑、分散劑等其他製劑用補助劑),而以乳劑、液劑、懸濁劑、水合劑、流性膠狀劑、粉劑、粒劑、錠劑、油劑、氣溶膠、薫煙劑等之任意的劑型來提供。
固體擔體方面,可舉例如滑石、膨潤土、黏土、高嶺土、矽藻土、蛭石、白碳、碳酸鈣等。
液體擔體方面,可舉例如甲醇、n-己醇、乙二醇等之醇類、丙酮、甲基乙基酮、環己酮等之酮類、n-己烷、煤油、燈油等之脂肪族烴類、甲苯、二甲苯、甲基萘等之芳香族烴類、二乙基醚、二氧陸圜、四氫呋喃等之醚類、醋酸乙基酯等之酯類、乙腈、異丁腈等之腈類、二甲基甲醯胺、二甲基乙醯胺等之酸醯胺類、大豆油、綿實油等之植物油類、二甲基亞碸、水等。
又,氣體狀擔體方面,可舉出LPG、空気、氮氣、碳酸氣體、二甲基醚等。
乳化、分散、展開附著等用之界面活性劑或分散劑方面,可使用例如烷基硫酸酯類、烷基(芳基)磺酸鹽類、聚氧烯基烷基(芳基)醚類、多元醇酯類、木質素磺酸鹽等。
又,改善製劑性狀用之補助劑方面,可使用例如羧基甲基纖維素、阿拉伯膠、聚乙二醇、硬脂酸鈣等。
上述之固體擔體、液體擔體、氣體狀擔體、界面活性劑、分散劑及補助劑,可因應需要而各自單獨使用或組合使用。
上述製劑中之有效成分的含量,並無特別限定,通常,在乳劑中為1~75重量%、在粉劑中為0.3~25重量%、在水合劑中為1~90重量%、在粒劑中為0.5~10重量%。
式(I)所示之新穎亞胺基吡啶衍生物、含此等之製劑、以及該等與其他有害生物防治劑之混合劑,可施用於有害昆蟲、植物、植物繁殖體(plant propagation materials;例如,種子、植物莖葉部、根部、土壤、水面、栽培用資材)以及必須防止害蟲侵入的房間等。此等之施用,係可於害蟲侵入之前及後進行。
含至少1種以式(I)所示之新穎亞胺基吡啶衍生物的有害生物防治劑,亦可施用於基因轉殖作物等。
較佳之態樣中,進一步包含農園藝上可容許之擔體的有害生物防治用組成物方面,可舉出(1)含有式(I)所示之新穎亞胺基吡啶衍生物0.1~80重量%、作為其他有害生物防治劑之殺蟲劑0.1~80重量%、潤濕劑及分散劑0.6~30重量%、增量劑20~95重量%所成的水合劑形態(wettable powder)之組成物、(2)含有式(I)所示之新穎亞胺基吡啶衍生物0.1~80重量%、作為其他有害生物防治劑之殺蟲劑0.1~80重量%、潤濕劑、分散劑及結合劑0.6~30重量%、增量劑20~95重量%所成的水合劑形態(water dispersible granule)之組成物、(3)含有式(I)所示之新穎亞胺基吡啶衍生物0.1
~80重量%、作為其他有害生物防治劑之殺蟲劑0.1~80重量%、分散劑、增黏劑、抗凍劑、防腐劑及消泡劑5~40重量%、水20~94重量%所成的流性膠狀劑形態(flowable)之組成物、(4)含有式(I)所示之新穎亞胺基吡啶衍生物0.1~80重量%、作為其他有害生物防治劑之殺蟲劑0.1~80重量%、乳化劑及乳化安定劑1~30重量%、有機溶媒20~97重量%所成的乳劑形態(emulsifiable concentrate)之組成物、(5)含有式(I)所示之新穎亞胺基吡啶衍生物0.1~80重量%、作為其他有害生物防治劑之殺蟲劑0.1~80重量%、增量劑70~99.8重量%所成的粉劑形態(dust)之組成物、(6)含有式(I)所示之新穎亞胺基吡啶衍生物0.1~80重量%、作為其他有害生物防治劑之殺蟲劑0.1~80重量%、增量劑70~99.8重量%所成的DL粉劑形態(low drift dust)之組成物、(7)含有式(I)所示之新穎亞胺基吡啶衍生物0.1~80重量%、作為其他有害生物防治劑之殺蟲劑0.1~80重量%、溶劑或結合劑0.2~10重量%、增量劑70~99.6重量%所成的微粒劑F形態(micro granule fine)之組成物、(8)含有式(I)所示之新穎亞胺基吡啶衍生物0.1~80重量%、作為其他有害生物防治劑之殺蟲劑0.1~80
重量%、造粒輔助劑(界面活性劑)及結合劑0.5~30重量%、增量劑20~98重量%所成的粒劑形態(granule)之組成物、(9)含有式(I)所示之新穎亞胺基吡啶衍生物0.1~80重量%、作為其他有害生物防治劑之殺蟲劑0.1~80重量%、被覆劑、乳化劑、分散劑及防腐劑1~50重量%、水20~98重量%所成的微膠囊劑形態(micro capsule)之組成物。較佳為(2)、(3)、(6)、(8)之組成物。
本發明之有害生物防治劑為動物寄生性害蟲防治劑時,可以液劑、乳劑、液化滴劑、噴霧劑、泡狀製劑、顆粒劑、細粒劑、粉劑、膠囊劑、丸劑、錠劑、嚼錠劑、注射劑、座劑、乳霜劑、洗髮精劑、潤洗劑、樹脂劑、燻煙劑、毒餌劑等之劑型來提供,但以液劑、液化滴劑所提供之劑型特別佳。此等之劑型,係可使用下述製藥學上所容許之擔體來製造。
液劑中,亦可再摻合一般的乳化劑、分散劑、展開附著劑、濕潤劑、懸濁化劑、保存劑、噴射劑等之製劑用補助劑等,再者,亦可摻合一般的塗膜形成劑。乳化、分散、展開附著等用之界面活性劑方面,可使用例如肥皂類、聚氧烯基烷基(芳基)醚類、聚氧乙烯烷基烯丙基醚類、聚氧乙烯脂肪酸酯、高級醇類、烷基芳基磺酸鹽等。
分散劑方面,可舉例如酪蛋白、明膠、多糖類、木質素衍生物、糖類、合成水溶性高分子等。展開附著.濕潤劑方面,可舉例如甘油、聚乙二醇等。懸濁化劑方面,可舉例如酪蛋白、明膠、羥基丙基纖維素、阿拉伯膠等。安定化劑方面,可舉例如苯酚系抗氧化劑(BHT、BHA等)、胺系抗氧化劑(二苯基胺等)、有機硫系抗氧化劑等。保存劑方面,可舉例如對羥基安息香酸甲基酯、對羥基安息香酸乙基酯、對羥基安息香酸丙基酯、對羥基安息香酸丁基酯等。上述之擔體、界面活性劑、分散劑及補助劑,可因應需要而各自單獨使用或組合使用。尚可再進一步含有香料、增效劑等。本發明之有害生物防治劑中之有效成分的含量,在液劑中通常以1~75重量%為宜。
用以調製乳霜劑之擔體方面,可舉例如非揮發性烴類(流動石蠟等)、羊毛脂氫化油脂類、高級脂肪酸、脂肪酸酯、動植物油、矽酮油、水。再者,乳化劑、保濕劑、抗氧化劑、香料、硼砂、紫外線吸收劑,亦可視其需要而各自單獨使用或組合使用。乳化劑方面,可舉例如脂肪酸山梨醇酐、聚氧乙烯烷基醚、脂肪酸聚氧乙烯等。本發明之有害生物防治劑中之有效成分的含量,若為乳霜劑一般以0.5~70重量%為適。
膠囊劑、丸劑或錠劑,乃將本發明之組成物中之有效成分與澱粉、乳糖、滑石等之擔體混合,再加入硬脂酸鎂等之崩壞劑及/或結合劑,視需要而可打錠使用。
用以調製注射劑之擔體方面,雖必須調製成無菌溶
液,但其中亦可含有其他物質,例如使該溶液與血液呈等張用之充分的鹽或葡萄糖。可用於調製注射劑之擔體方面,可舉出甘油酯、安息香酸苯甲基酯、肉豆蔻酸異丙基酯及丙二醇的脂肪酸衍生物等之酯、N-甲基吡咯啶酮、甘油縮甲醛般的有機溶媒。本發明之有害生物防治劑中之有效成分的含量,若為注射劑則一般以0.01~10重量%為適。
用以調製樹脂劑之擔體方面,可舉例如氯化乙烯基系聚合物、聚胺基甲酸酯等。此等之基材中,可視需要而添加鄰苯二甲酸酯類、已二酸酯類、硬脂酸等之可塑劑。於該基材中混練真有效成分後,可藉由射出成型、押出成型、加壓成型等來予以成型。再者,經過適當宣染、成型、裁斷等之步驟,亦可作為動物用耳標、動物用防蟲項圈。
毒餌劑用之擔體方面,可舉出餌物質及誘引物質(小麥粉、玉米粉等之穀粉、玉米澱粉、馬鈴薯澱粉等之澱粉、特級白砂糖、麥芽糖、蜂蜜等之糖類、甘油、洋蔥香料、牛奶香料等之食品香料、蛹粉、魚粉等之動物性粉末、各種費洛蒙等)。本發明之有害生物防治劑中有效成分的含量,若為毒餌劑一般以0.0001~90重量%為適。
本發明之有害生物防治用組成物,係可預先調製各自單獨含有作為該組成物中之有效成分之式(I)所示之新穎亞胺基吡啶衍生物、或該等之酸加成鹽的至少1種與其他有害生物防治劑的至少1種所成的製劑形態,並於使用
時,再將此等當場混合使用。
因此,根據本發明之別的態樣,係可提供含有作為有效成分之式(I)所示之新穎亞胺基吡啶衍生物、或該等之酸加成鹽的至少1種與其他有害生物防治劑的至少1種所成的組合物。
根據本發明之別的較佳樣態,係可提供前述組合物中,含有以式(I)所示之新穎亞胺基吡啶衍生物、或該等之酸加成鹽作為有效成分所成的第1組成物,以及含有以其他有害生物防治劑作為有效成分所成的第2組成物。此時,第1組成物與第2組成物,係與前述有害生物防治用組成物的情況相同,可併用適當的擔體或補助劑而為任意的劑型。該組合物亦可以藥劑組般的形態提供。
又根據本發明之其他態樣,係可提供一種自有害生物保護有用植物或動物之方法,其係含有將作為有效成分之式(I)所示之新穎亞胺基吡啶衍生物、其鏡像異構物、該等之混合物、或該等之酸加成鹽的至少1種與其他有害生物防治劑的至少1種,同時或個別施用於應處理之區域(較佳為將各成分同時施用)所成之方法。
此方法中,「同時」施用係包含,將式(I)所示之新穎亞胺基吡啶衍生物、或該等之酸加成鹽的至少1種與其他有害生物防治劑的至少1種對應處理之區域施用之前予以混合,而施用該混合物。「個別」施用則不將該等預先混合,而是包含使式(I)所示之新穎亞胺基吡啶衍生物、或該等之酸加成鹽較其他成分先予以施用、使式
(I)所示之新穎亞胺基吡啶衍生物、或該等之酸加成鹽較其他成分後予以施用。
又再根據本發明之別的較佳樣態,係可提供一種自有害生物保護有用植物或動物之方法,其係含有將(1)含有式(I)所示之新穎亞胺基吡啶衍生物、或該等之酸加成鹽的至少1種作為有效成分所成之第1組成物、與(2)含有其他有害生物防治劑的至少1種作為有效成分所成之第2組成物
施用於應處理之區域所成者。
根據本發明之別的態樣,係可提供一種自有害生物保護有用植物之方法,乃是含有將本發明之組成物或組合物以直接或是經稀釋後施用於作為施用對象之有害生物、有用植物、有用植物的種子、土壤、栽培擔體或動物,較佳為施用於有用植物、土壤或動物所成者。
根據本發明之別的態樣,係可提供一種本發明之組成物或組合物的使用,其係用以自有害生物保護有用植物或動物之使用。
又,在將本發明之組成物或組合物施用於作為施用對象之有害生物、有用植物、有用植物的種子、土壤或栽培擔體的手法方面,較佳可舉出散佈處理、水面處理、土壤處理(混入、灌注等)、育苗箱處理、表面處理(塗佈、粉衣、被覆)、或薫蒸處理(土壤注入後,於以聚薄膜覆蓋土壤所密閉而成的空間中之處理)等,更佳可舉出水面
處理、土壤處理、育苗箱處理、或表面處理。
以對植物進行散佈處理而施用時的處理量,在本發明之組成物中之有效成分量方面,係以耕地每10公畝施用0.1g~10kg,較佳為1g~1kg為宜。
又,處理植物的種子、根、塊莖、球根或根莖之方法方面,例如,對種子而言,係有浸漬法、粉衣法、塗沫法、吹附法、壓粒法、皮膜法、薫蒸法。
浸漬法係將種子浸漬於液狀藥劑液中之方法,粉衣法中,則有使粉狀的藥劑附著於乾燥狀的種子之乾粉衣法以及使粉狀的藥劑附著於輕浸過水中的種子之濕粉衣法。又有將懸濁狀的藥劑在混練機內塗佈於種子之表面的塗沫法、吹附於種子表面之吹附法。再者,使種子與填充劑一起壓粒化成一定大小形狀時,於填充物中混入藥劑來進行處理之壓粒法、或是將含藥劑之薄膜包覆於種子之皮膜法、於密閉容器內藉由經氣體化之藥劑消毒種子之薫蒸法。
本發明之組成物的較佳之處理法方面,可舉出浸漬法、粉衣法、塗沫法、吹附法、壓粒法、皮膜法。
又,種子以外,亦可施用於發芽後或自土壤出芽後所移植、已發芽之植物以及幼苗植物。藉由以浸漬所為之全體或部分之處理,係可在移植之前保護此等植物。
施用於植物的種子時之處理量,並無特別限定,作為本發明之組成物中的有效成分量,係以種子每100kg施用1g~10kg為佳,更佳為100g~1kg。
又,本發明之組成物的土壤施用方法方面,並無特別限定,較佳可舉出下述之方法。
可舉出將含本發明之組成物的粒劑施用於土壤中或土壤上。特佳之土壤施用方法係散佈、帶、溝、及插秧穴施用法。
又有,藉由將已乳化或溶解於水中的本發明之組成物所成的溶液灌注於土壤中而施用之較佳的土壤施用方法。
此等以外,較佳之土壤施用方法的例子方面,可舉出蔬菜及花卉類生產用的水耕栽培及砂耕、NFT(Nutrient Film Technique)、岩綿耕等之固形培養基耕栽培般的養液栽培系統中之養液中的使用、或者是稻米育苗用之育苗箱中的施用(床土混和等)。亦可直接施用於含蛭石之人工培土及含育苗用人工地墊之固形培養基。
水面、育苗箱或土壤中之本發明組成物的處理量,並無特別限定,有效成分方面,係以耕地每10公畝為0.1g~10kg,較佳為1g~1kg。又,將本發明之組成物或組合物施用於施用生物的手法方面,係有將本發明之有害生物防治組成物藉由經口或注射而投予到施用生物的體內、投予至施用動物的體表全體或部分、或將經製劑化成樹脂製劑或薄片製劑之本防治劑裝附於施用生物上而得以防治有害生物。又,可藉由於預想有害蟲侵入、寄生、移動的場所被覆本發明之有害生物組成物,而得以防治有害生物。
本發明之有害生物組成物,雖可直接使用,但須視情況而可於水、液狀之擔體、市售之洗髮精、潤洗、餌、飼
養舍地墊等稀釋使用。
本有害生物防治組成物稀釋於乳劑、流性膠狀劑、水合劑等的稀釋液(水)來使用時,並無特別限制,但可藉由使有效成分之濃度成10~10000ppm來稀釋於水中進行散佈來施用。又,將本有害生物防治組成物投予至對象生物時,該投予量並無特別限定,經皮投予時,對象生物的體重每1kg係投予本組成物的量0.01~500mg之範圍內。經口投予時,對象生物的體重每1kg係投予本組成物的量0.01~100mg之範圍內。將樹脂製劑裝附於對象生物時,樹脂製劑中所含本組成物的量,較佳為每單位樹脂製劑重量為0.01~50重量%之範圍內。
以下列舉實施例來具體地說明本發明,本發明並不受限於此等的實施例。
(1)將2-胺基吡啶25g(270mmol)溶解於無水二氯甲烷200ml中,並加入三乙基胺41ml(30g,300mmol)後,冷卻至0℃。於其中,花15分鐘滴下無水三氟醋酸38ml(57g,270mmol),在室溫下攪拌2小時。反應終了後,將反應液注入約100ml的冰水中,攪拌10分鐘。移至分液漏斗中進行分液,將有機層以150ml的水洗淨2次、以150ml的1%HCL水溶液洗淨2次後,以無水硫酸
鎂予以乾燥,減壓濃縮而得2,2,2-三氟-N-(吡啶-2(1H)-亞基)乙醯胺36g(產率71%)。
1H-NMR(CDCl3,δ,ppm):7.20(1H,ddd)、7.83(1H,td)、8.20(1H,d)、8.35(1H,d),10.07(1H,brs)
13C-NMR(CDCl3,δ,ppm):115.3,115.5(q),121.6,139.1,147.9,149.5,155.3(q)
MS:m/z=191(M+H)
(2)將2-氯-5-氯甲基吡啶20g(126mmol)溶解於無水乙腈200ml中,加入以前述方法所得之2,2,2-三氟-N-(吡啶-2(1H)-亞基)乙醯胺24g(126mmol)、碳酸鉀21g(151mmol),加熱迴流6小時後,在室溫攪拌10小時。反應終了後,過濾反應液,並減壓濃縮濾液。於其中加入二乙基醚予以結晶化,濾取所得之結晶,以二乙基醚與水充分地洗淨。將所得之結晶以60℃減壓乾燥1小時,得到目的物。產量26g(產率66%)。
1H-NMR(CDCl3,δ,ppm):5.57(2H,s)、6.92(1H,td)、7.31(1H,d)、7.80(1H,td)、7.87(1H,dd)、7.99(1H,dd)、8.48(2H,m)
13C-NMR(CDCl3,δ,ppm):53.8,115.5,117.2(q),122.1,124.7,130.0,139.2,140.0,142.5,149.7,151.8,158.9,163.5(q)
MS:m/z=316(M+H)
(3)粉末X線結晶解析
粉末X線繞射中,係以下述之條件進行測定。
裝置名:RINT-2200(股份公司理學(Rigaku))
X線:Cu-Kα(40kV、20mA)
掃瞄範圍:4~40°採樣幅度:0.02°掃瞄速度:1°/分
結果係如下所示。
繞射角(2θ)8.7°、14.2°、17.5°、18.3°、19.8°、22.4°、30.9°、35.3°
(4)差示掃瞄熱量分析(DSC)
差示掃瞄熱量分析中,係以下述之條件進行測定。
裝置名:DSC-60
試料槽:鋁
溫度範圍:50℃~250℃(昇溫:10℃/分)
結果顯示,融點為155~158℃。
合成例P1之別法
將2-氯-5-氯甲基吡啶3.00g(18.6mmol)溶解於無水DMF20ml中,加入2-胺基吡啶1.75g(18.6mmol)後,在80℃攪拌8小時、在室溫攪拌5小時。反應終了後,減壓餾去DMF,加入乙腈後即刻有固體析出,濾取,並以乙腈充分地洗淨後予以乾燥,得到1-〔(6-氯吡啶-3-基)甲基〕吡啶-2(1H)-亞胺鹽酸鹽2.07g(產率44%)。
1H-NMR(DMSO-d6,δ,ppm):5.65(2H,s)、6.96(1H,t)、7.23(1H,m)、7.57(1H,d)、7.80(1H,m)、7.91(1H,m)、8.28(1H,m)、8.49(1H,d)、9.13(2H,brs)
將以前述方法所得之1-〔(6-氯吡啶-3-基)甲基〕吡啶-2(1H)-亞胺鹽酸鹽50mg(0.20mmol)溶解於無水二氯甲烷5ml中,在冰冷下依序加入DMAP 122mg(1.00mmol)、無水三氟醋酸50mg(0.24mmol),在室溫攪拌1小時。反應終了後,將反應液以二氯甲烷稀釋,並以1%鹽酸洗淨後,以無水硫酸鎂進行乾燥。減壓餾去二氯甲烷,得到目的物。產量42mg(產率67%)。NMR係與前述方法者一致。
將合成例P1之別法中記載之方法所得的1-〔(6-氯吡啶-3-基)甲基〕吡啶-2(1H)-亞胺鹽酸鹽200mg(0.78mmol)、DMAP238mg(1.95mmol)、EDC-HCl224mg(1.17mmol)溶解於無水二氯甲烷10ml中,加入二溴醋酸101μl(202mg,1.17mmol)後在室溫攪拌一晚。反應終了後,以二氯甲烷稀釋反應液,以水洗淨1次、以1%HCl水溶液洗淨2次後,以無水硫酸鎂予以乾燥,減壓濃縮後得到目的物。產量50mg(產率15%)
1H-NMR(CDCl3,δ,ppm):5.56(2H,s),5.99(1H,s)、6.78(1H,td)、7.33(1H,d)、7.69(1H,td)、7.76(1H,dd)、7.93(1H,dd)、8.39(1H,d)、8.50(1H,d)
13C-NMR(CDCl3,δ,ppm):44.6,53.1,113.7,121.9,124.8,130.1,138.2,139.7,141.2,149.5,
152.0,159.4,172.2
MS:m/z=418(M+H)
將2-氯-3-氟-5-甲基吡啶4.00g(27.6mmol)溶解於四氯化碳80ml中,加入N-溴琥珀醯亞胺7.37g(41.4mmol)、過氧化苯甲醯20mg,加熱迴流一晚。反應終了後,將反應液恢復至室溫後予以減壓濃縮,以二氧化矽膠體層析(己烷:醋酸乙基酯=19:1)予以純化,得到5-(溴甲基)-2-氯-3-氟吡啶3.06g(產率51%)。
1H-NMR(CDCl3,δ,ppm):4.45(2H,s)、7.54(1H,dd)、8.23(1H,s)
將以上述方法所得之5-(溴甲基)-2-氯-3-氟吡啶50mg(0.22mmol)溶解於無水乙腈5ml中,依序加入參考例1之(1)中記載之方法所得的2,2,2-三氟-N-(吡啶-2(1H)-亞基)乙醯胺42mg(0.22mmol)、碳酸鉀36mg(0.26mmol),加熱迴流7小時。反應終了後,將反應液恢復至室溫後過濾不溶物,將濾液減壓濃縮。於其中加入二乙基醚後即刻有固體析出,將其濾取,以二乙基醚洗淨後,以真空乾燥器減壓乾燥而得目的物。產量29mg(產率40%)。
1H-NMR(CDCl3,δ,ppm):5.54(2H,s)、6.89(1H,td)、7.76(1H,dd)、7.80(1H,td)、7.85(1H,d)、8.29(1H,d)、8.57(1H,d)
MS:m/z=334(M+H)
將2-氟-5-甲基吡啶500mg(4.50mmol)溶解於四氯化碳50ml中,加入N-溴琥珀醯亞胺1.20g(6.76mmol)、過氧化苯甲醯20mg,加熱迴流2.5小時。反應終了後,將反應液恢復至室溫,減壓餾去溶媒,以二氧化矽膠體層析(己烷:醋酸乙基酯=19:1)予以純化,得到5-溴甲基-2-氟吡啶300mg(產率35%)。
將以上述方法所得之5-溴甲基-2-氟吡啶57mg(0.30mmol)溶解於無水乙腈10ml中,依序加入以合成例P1之(1)中記載之方法合成的2,2,2-三氟-N-(吡啶-2(1H)-亞基)乙醯胺57mg(0.30mmol)、碳酸鉀69mg(0.50mmol),加熱迴流6小時。反應終了後,將反應液恢復至室溫後過濾不溶物,將濾液減壓濃縮。以二氧化矽膠體層析(己烷:醋酸乙基酯=1:1→3:1)純化,得到目的物。產量21mg(產率23%)。
1H-NMR(CDCl3,δ,ppm):5.56(2H,s)、6.89(1H,td)、6.94(1H,d)、7.79(1H,td)、7.87(1H,d)、8.03(1H,m)、8.31(1H,s)、8.54(1H,d)
MS:m/z=300(M+H)
將2-溴-5-甲基吡啶500mg(2.92mmol)溶解於四氯
化碳15ml中,加入N-溴琥珀醯亞胺623mg(3.50mmol)、過氧化苯甲醯10mg,加熱迴流19小時。反應終了後,將反應液恢復至室溫後予以減壓濃縮,以二氧化矽膠體層析(己烷;醋酸乙基酯=19:1)予以純化,得到2-溴-5-溴甲基吡啶143mg(產率20%)。
1H-NMR(CDCl3,δ,ppm):4.42(2H,s)、7.47(1H,d)、7.59(1H,dd)、8.38(1H,d)
將以上述方法所得之2-溴-5-溴甲基吡啶70mg(0.28mmol)溶解於無水乙腈10ml中,依序加入以合成例P1之(1)中記載之方法合成的2,2,2-三氟-N-(吡啶-2(1H)-亞基)乙醯胺54mg(0.28mmol)、碳酸鉀46mg(0.34mmol),加熱迴流6小時。反應終了後,將反應液恢復至室溫後過濾不溶物,將濾液減壓濃縮。於其中加入二乙基醚後即刻有固體析出,將其濾取,以二乙基醚洗淨後以真空乾燥器減壓乾燥而得目的物。產量81mg(產率82%)。
1H-NMR(CDCl3,δ,ppm):5.52(2H,s)、6.88(1H,t)、7.48(1H,d)、7.78(2H,m)、7.84(1H,d)、8.44(1H,d)、8.53(1H,d)
MS:m/z=360(M+H)
將合成例P1之別法中記載之方法所得的1-〔(6-氯吡啶-3-基)甲基〕吡啶-2(1H)-亞胺鹽酸鹽70mg
(0.27mmol)溶解於無水二氯甲烷4ml中,依序加入DMAP 82mg(0.67mmol)、氯醋酸25mg(0.27mmol)、EDC-HCl 62mg(0.32mmol),在室溫攪拌一晚。反應終了後,加入二氯甲烷予以稀釋,以水、1%之HCl aq.予以洗淨,以無水硫酸鎂進行乾燥後,減壓濃縮後得到目的物。產量4mg(產率5%)。
1H-NMR(CDCl3,δ,ppm):4.17(2H,s),5.46(2H,s)、6.64(1H,td)、7.31(1H,d)、7.60(1H,td)、7.64(1H,dd)、7.80(1H,dd)、8.32(1H,d)、8.45(1H,d)
MS:m/z=296(M+H)
將2-胺基吡啶400mg(4.26mmol)溶解於無水二氯甲烷10ml中,加入二氟醋酸322μl(490mg、5.11mmol)、EDC-HCl982mg(5.10mmol)、DMAP 622mg(5.11mmol),在室溫攪拌61小時。反應終了後,以二氯甲烷稀釋反應液,以水洗淨1次、以1%HCl aq.洗淨2次後,以無水硫酸鎂予以乾燥,減壓濃縮而得2,2-二氟-N-(吡啶-2(1H)-亞基)乙醯胺102mg(產率14%)。
1H-NMR(CDCl3,δ,ppm):6.03(1H,t)、7.15(1H,m)、7.78(1H,td)、8.20(1H,d)、8.34(1H,dd)、8.72(1H,brs)
將以上述方法所得之2,2-二氟-N-(吡啶-2(1H)-亞
基)乙醯胺100mg(0.58mmol)溶解於無水乙腈10ml中,將2-氯-5-氯甲基吡啶94mg(0.58mmol)溶解於無水乙腈5ml後加入,接著加入碳酸鉀84mg(0.63mmol),加熱迴流140分鐘。反應終了後,將反應液恢復至室溫,濾取不溶物並去除,再予減壓濃縮。於其中加入醚即有固體析出,將其濾取,充分地乾燥後得到目的物。產量63mg(產率37%)。
1H-NMR(CDCl3,δ,ppm):5.52(2H,s),5.90(1H,t)、6.79(1H,td)、7.33(1H,d)、7.71(1H,m)、7.77(1H,dd)、7.85(1H,dd)、8.45(1H,d)、8.50(1H,d)
13C-NMR(DMSO-d6,δ,ppm):53.0,111.0(t),115.2,120.7,124.7,131.7,140.6,141.6,143.2,150.4,150.9,158.3,169.4(t)
MS:m/z=298(M+H)
將2-胺基吡啶200mg(2.13mmol)溶解於二氯甲烷5ml中,依序加入EDC-HCl 491mg(2.55mmol)、DMAP 311mg(2.55mmol)、氯二氟醋酸187μl(2.23mmol、290mg),攪拌一晚。反應終了後,以二氯甲烷稀釋反應液,以水、1%鹽酸洗淨後,以無水硫酸鎂進行乾燥後,得到2-氯-2,2-二氟-N-(吡啶-2(1H)-亞基)乙醯胺105mg(產率24%)。
1H-NMR(CDCl3,δ,ppm):7.19(1H,dd)、7.82(1H,m)、8.18(1H,d)、8.36(1H,d)、9.35(1H,brs)
於以上述方法合成之2-氯-2,2-二氟-N-(吡啶-2(1H)-亞基)乙醯胺68mg(0.33mmol)中,加入已溶解於無水乙腈6ml之2-氯-5-氯甲基吡啶53mg(0.33mmol),接著加入碳酸鉀50mg(0.36mmol),加熱迴流1小時。反應終了後,將反應液恢復至室溫之後進行減壓濃縮。於其中加入二乙基醚後即有固體析出,將其濾取,藉由乾燥而得目的物。產量49mg(產率45%)。
1H-NMR(CDCl3,δ,ppm):5.56(2H,s)、6.92(1H,t)、7.33(1H,d)、7.82(1H,m)、7.91(1H,dd)、8.02(1H,d)、8.45(1H,d)、8.48(1H,d)
13C-NMR(CDCl3,δ,ppm):53.8,115.2,120.1(t),122.1,124.8,139.0,140.0,142.3,150.0,151.9,159.1,159.1,165.8(t)
MS:m/z=332(M+H)
將合成例P1之別法中記載之方法所得的1-〔(6-氯吡啶-3-基)甲基〕吡啶-2(1H)-亞胺鹽酸鹽70mg(0.27mmol)溶解於無水二氯甲烷4ml中,依序加入三乙基胺94μl(0.68mmol、68mg)、三氯乙醯氯33μg(0.27mmol、49mg),在室溫攪拌1小時。反應終了
後,加入水而反應停止,以二氯甲烷與水進行分液。將有機層以水洗淨1次、以1%鹽酸洗淨2次後,以無水硫酸鎂予以乾燥,並減壓濃縮。於其中加入二乙基醚後,即有固體析出,將其濾取,並予以乾燥而得目的物。產量61mg(產率62%)。
1H-NMR(CDCl3,δ,ppm):5.59(2H,s)、6.86(1H,t)、7.32(1H,d)、7.78(1H,td)、7.91(2H,m)、8.43(1H,d)、8.50(1H,d)
MS:m/z=364(M+H)
將2-胺基吡啶300mg(3.19mmol)溶解於無水二氯甲烷15ml中,依序加入EDC-HCl 919mg(4.78mmol)、DMAP 583mg(4.78mmol)、五氟戊酸397μl(628mg、3.83mmol),在室溫攪拌一晚。反應終了後,以二氯甲烷稀釋反應液,以水洗淨1次、以1%鹽酸洗淨2次後,以無水硫酸鎂予以乾燥,減壓濃縮而得2,2,3,3,3-五氟-N-(吡啶-2(1H)-亞基)戊炔草胺85mg(產率11%)。
於以上述方法所得之2,2,3,3,3-五氟-N-(吡啶-2(1H)-亞基)戊炔草胺77mg(0.32mmol)中,加入已溶解於無水乙腈8ml的2-氯-5-氯甲基吡啶52mg(0.32mmol)、碳酸鉀49mg(0.35mmol),加熱迴流11小時。反應終了後,將反應液恢復至室溫後過濾不溶物,將濾液減壓濃縮。以二氧化矽膠體層析(己烷:醋酸乙基
酯=1:3)純化,得到目的物。產量12mg(產率10%)。
1H-NMR(CDCl3,δ,ppm):5.56(2H,s)、6.90(1H,td)、7.32(1H,d)、7.79(2H,m)、7.84(1H,d)、8.43(1H,d)、8.56(1H,d)
MS:m/z=366(M+H)
將2-氯-5-甲基嘧啶1.04g(8.13mmol)溶解於四氯化碳30ml中,加入N-溴琥珀醯亞胺1.73g(9.75mmol)、過氧化苯甲醯20mg,加熱迴流6小時。反應終了後,將反應液恢復至室溫後予以減壓濃縮,以二氧化矽膠體層析(己烷:醋酸乙基酯=3:1)予以純化而得5-溴甲基-2-氯吡啶641mg(產率38%)。
1H-NMR(CDCl3,δ,ppm):4.42(2H,s)、8.66(2H,s)
將以上述方法所得之5-溴甲基-2-氯吡啶104mg(0.50mmol)溶解於無水乙腈6ml中,加入合成例P1之(1)中記載之方法所得的2,2,2-三氟-N-(吡啶-2(1H)-亞基)乙醯胺96mg(0.50mmol)、碳酸鉀76mg(0.55mmol),加熱迴流1小時。反應終了後,將反應液恢復至室溫,過濾不溶物後去除,將濾液減壓濃縮。於其中加入二乙基醚後即刻有固體析出,將其濾取,以二乙基醚洗淨後置入真空乾燥器中予以減壓乾燥而得目的物。產
量92mg(產率58%)。
1H-NMR(CDCl3,δ,ppm):5.54(2H,s)、6.98(1H,m)、7.87(1H,m)、8.18(1H,m)、8.48(1H,m)、8.83(2H,m)
13C-NMR(CDCl3,δ,ppm):60.0,115.6,117.1(q),122.1,127.5,139.2,142.9,158.8,160.3(2C),161.4,163.8(q)
MS:m/z=317(M+H)
以依據合成例P1~P11之方法,合成下述表中所示之P213~P226、P228、P230、P232~P234、P240、P244的化合物。
(1)將2-胺基吡啶400mg(4.26mmol)溶解於無水二氯甲烷10ml中,加入二氟醋酸322μl(490mg、5.11mmol)、EDC-HCl 982mg(5.10mmol)、DMAP 622mg(5.11mmol),在室溫攪拌61小時。反應終了後,以二氯甲烷稀釋反應液,以水洗淨1次、以1%HCl aq.洗淨2次後,以無水硫酸鎂予以乾燥,減壓濃縮而得2,2-二氟-N-(吡啶-2(1H)-亞基)乙醯胺102mg(產率14%)。
1H-NMR(CDCl3,δ,ppm):6.03(1H,t)、7.15(1H,m)、7.78(1H,td)、8.20(1H,d)、8.34(1H,dd)、8.72(1H,brs)
(2)將5-溴甲基-2-氟吡啶128mg(0.75mmol)溶解於無水DMF 3ml中,將2,2-二氟-N-〔吡啶-2(1H)-亞基〕乙醯胺116mg(0.68mmol)溶解於無水DMF 3ml中後加入,接著加入碳酸鉀103mg(0.75mmol),在65℃攪拌2小時。反應終了後,將反應液恢復至室溫,加入醋酸乙基酯與水進行分液。將有機層以1%鹽酸洗淨後,以無水硫酸鎂予以乾燥,並減壓濃縮。於其中加入少量的己烷與二乙基醚時,即有結晶析出,將其濾取,予以乾燥而得目的物。產量50mg(產率26%)。
(1)將2-氯-5-氯甲基吡啶300mg(1.86mmol)溶解於無水DMF6ml中,加入2-胺基嘧啶118mg(1.24mmol),在80℃攪拌8小時。反應終了後,將反應液恢復至室溫,減壓餾去DMF。於其中加入二乙基醚時,於茄形燒瓶之壁面發生結晶化。將二乙基醚以傾析法去除,充分地乾燥而得1-((6-氯吡啶-3-基)甲基)嘧啶-2(1H)-亞胺鹽酸鹽。產量107mg(產率34%)
(2)將以上述方法所得之1-((6-氯吡啶-3-基)甲基)嘧啶-2(1H)-亞胺鹽酸鹽71mg(0.27mmol)懸濁於無水二氯甲烷5ml中,依序加入三乙基胺114μl(0.83mmol,83mg)、三氟醋酸酐53μl(0.38mmol),在室溫攪拌2小時。反應終了後,於反應液中加入二氯甲烷與水進行分液,將有機層以無水硫酸鎂進行乾燥後予以減壓濃縮。於其中加入少量的二乙基醚時,即有結晶析出,將其濾取,以少量的二乙基醚洗淨後,予以乾燥而得目的物。產量24mg(產率28%)。
(1)將2-氯-5-氯甲基吡啶3.00g(18.6mmol)溶解於無水DMF20ml中,加入2-胺基吡啶1.75g(18.6mmol)後,在80℃攪拌8小時、在室溫攪拌5小時。反應終了後,減壓餾去DMF,加入乙腈後即刻有固體析出,濾取,並以乙腈充分地洗淨後予以乾燥,得到1-〔(6-氯吡啶-3-基)甲基〕吡啶-2(1H)-亞胺鹽酸鹽2.07g(產率44%)。
1H-NMR(DMSO-d6,δ,ppm):5.65(2H,s)、6.96(1H,t)、7.23(1H,m)、7.57(1H,d)、7.80(1H,m)、7.91(1H,m)、8.28(1H,m)、8.49(1H,d)
(2)於以前述方法所得之1-〔(6-氯吡啶-3-基)甲基〕吡啶-2(1H)-亞胺鹽酸鹽150mg(0.66mmol)中加入無水乙腈10ml,加入4-硝基苯基(2,2,2-三氟乙基)胺基甲酸酯177mg(0.66mmol)、碳酸鉀200mg(1.46mmol),在50℃攪拌2小時。反應終了後,將反應液恢復至室溫,濾取不溶物並去除,再予減壓濃縮。於其中加入二氯甲烷與水進行分液,將有機層以1%鹽酸洗淨後,以無水硫酸鎂予以乾燥,並減壓濃縮。
於其中加入少量的二乙基醚時,即有結晶析出,將其濾取,充分地乾燥後得到目的物。產量48mg(產率
21%)。
(1)將2-胺基吡啶25g(270mmol)溶解於無水二氯甲烷200ml中,並加入三乙基胺41ml(30g,300mmol)後,冷卻至0℃。於其中,花15分鐘滴下無水三氟醋酸38ml(57g,270mmol),在室溫下攪拌2小時。反應終了後,將反應液注入約100ml的冰水中,攪拌10分鐘。移至分液漏斗中進行分液,將有機層以150ml的水洗淨2次、以150ml的1%HCL水溶液洗淨2次後,以無水硫酸鎂予以乾燥,減壓濃縮而得2,2,2-三氟-N-(吡啶-2(1H)-亞基)乙醯胺36g(產率71%)。
1H-NMR(CDCl3,δ,ppm):7.20(1H,m)、7.83(1H,m)、8.20(1H,d)、8.35(1H,d),10.07(1H,brs)
13C-NMR(CDCl3,δ,ppm):115.3,115.5(q),121.6,139.1,147.9,149.5,155.3(q)
(2)將2-氯-5-氯甲基吡啶20g(126mmol)溶解於無水乙腈200ml中,加入以前述方法所得之2,2,2-三氟-N-(吡啶-2(1H)-亞基)乙醯胺24g(126mmol)、碳酸鉀21g(151mmol),加熱迴流6小時後,在室溫攪拌10小
時。反應終了後,過濾反應液,並減壓濃縮濾液。於其中加入二乙基醚予以結晶化,濾取所得之結晶,以二乙基醚與水充分地洗淨。將所得之結晶以60℃減壓乾燥1小時,得到N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙醯胺(P212)。產量26g(產率66%)。
1H-NMR(CDCl3,δ,ppm):5.57(2H,s)、6.92(1H,td)、7.31(1H,d)、7.80(1H,td)、7.87(1H,dd)、7.99(1H,dd)、8.48(2H,m)
13C-NMR(CDCl3,δ,ppm):53.8,115.5,117.2(q),122.1,124.7,130.0,139.2,140.0,142.5,149.7,151.8,158.9,163.5(q)
MS:m/z=316(M+H)
(3)於五硫化二磷16.3g(36.7mmol)中加入甲苯180ml,加入碳酸鈉6.72g(63.4mmol)後,在室溫攪拌5分鐘。於其中,加入以前述方法所得之N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙醯胺20.0g(63.4mmol),在50℃攪拌19小時。於反應液中加入醋酸乙基酯150ml,在50℃攪拌10分鐘後,過濾不溶物後去除,使用醋酸乙基酯250ml充分清洗。將其移至分液漏斗中,以飽和碳酸氫鈉水300ml、飽和食鹽水200ml洗淨後,減壓濃縮。於其中加入水200ml時,即有結晶析出。
在室溫攪拌1小時後,濾取結晶,以水150ml洗淨2
次、以己烷150ml進行2次淤漿洗淨,在60℃減壓乾燥2小時而得目的物。產量19.5g(產率94%)。
1H-NMR(CDCl3,δ,ppm):5.48(2H,s)、7.12(1H,td)、7.34(1H,d)、7.77(1H,dd)、7.96(1H,m)、8.05(1H,dd)、8.45(1H,d)、8.56(1H,d)
MS:m/z=332(M+H)
將以合成例4之方法合成的N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙硫醯胺(1-20)150mg(0.45mmol)溶解於甲醇5ml中,加入甲基胺(40%甲醇溶液)105μl(42mg,1.36mmol)、碳酸銀124mg(0.45mmol),在50℃攪拌1小時。反應終了後,將反應液恢復至室溫,使用矽藻土以真空抽吸過濾以去除不溶物。於其中加入醋酸乙基酯與水後進行分液,將有機層以無水硫酸鎂進行乾燥後,予以減壓濃縮,以二氧化矽膠體層析(己烷:醋酸乙基酯=1:1)純化,得到目的物。產量81mg(產率56%)。
將以合成例4之方法合成的N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙硫醯胺(1-20)30mg(0.09mmol)溶解於乙醇5ml中,加入O-烯丙基羥基胺鹽酸鹽50mg(0.45mmol)、三乙基胺62μl(0.45mmol、45mg)、碳酸銀25mg(0.09mmol),在50℃攪拌5小時20分鐘。反應終了後,將反應液恢復至室溫,過濾不溶物後予以去除。將濾液減壓濃縮,以醋酸乙基酯與1%鹽酸進行分液後,將醋酸乙基酯層以飽和食鹽水洗淨,以無水硫酸鎂進行乾燥後,減壓濃縮。將此以TLC薄層層析板(0.5mm薄層層析板1片、以己烷:醋酸乙基酯=1:1展開)純化,得到目的物。產量15mg(產率45%)。
於以合成例4之方法合成的N-〔1-((6-氯吡啶-3-
基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙硫醯胺(1-20)1.00g(3.00mmol)中加入乙醇25ml,依序加入羥基胺鹽酸鹽1.04g(15.0mmol)、三乙基胺2.00ml(1.50g,15.0mmol),在50℃攪拌21小時30分鐘。反應終了後,於反應液中加入醋酸乙基酯與1%鹽酸來進行分液,將有機層以水洗淨後,以無水硫酸鎂予以乾燥,並減壓濃縮。將此以二氧化矽膠體層析(己烷:醋酸乙基酯=1:1)純化,得到目的物。產量625mg(產率63%)。
將以合成例7之方法合成的N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟-N’-羥基乙脒(1-499)30mg(0.09mmol)溶解於無水乙腈3ml中,依序加入三乙基胺24μl(17mg,0.17mmol)、鹽化苯甲醯基20μg(22mg,0.17mmol),在室溫攪拌10分鐘。反應終了後,於反應液中加入醋酸乙基酯與1%鹽酸來進行分液,將有機層以水洗淨後,以無水硫酸鎂進行乾燥,並予以減壓濃縮。將此以TLC薄層層析板(0.5mm薄層層析板1
片、以己烷:醋酸乙基酯=1:1展開)純化,得到目的物。產量26mg(產率67%)。
於正丙基異氰酸酯11mg(0.13mmol)中加入無水乙腈5ml,加入以合成例7之方法合成的N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟-N’-羥基乙脒(1-499)40mg(0.12mmol)、鉀-t-丁氧化物4mg(0.04mmol),在室溫攪拌1小時。反應終了後,將反應液予以減壓濃縮,加入醋酸乙基酯與飽和食鹽水來進行分液。將醋酸乙基酯層以無水硫酸鎂進行乾燥後,予以減壓濃縮,以TLC薄層層析板(0.5mm薄層層析板1片、己烷:醋酸乙基酯=1:3展開)純化,得到目的物。產量16mg(產率32%)
將以前述方法所得之1-〔(6-氯吡啶-3-基)甲基〕吡啶-2(1H)-亞胺鹽酸鹽4.0g(15.7mmol)懸濁於二氯甲烷24.6ml中,於冰冷下將三鹽化磷1.35ml花約10分鐘滴下,接著滴下已溶解於二氯甲烷37ml中之三乙基胺3.16g(31.2mmol)。恢復至室溫後攪拌約2小時,之後,加入硫499mg(15.6mmol),在室溫攪拌一晚。接著冰冷反應液,依序滴下三乙基胺3.16g(31.2mmol)、已溶解於二氯甲烷10ml中之2-丙硫醇2.38g(31.2mmol),在室溫攪拌1日。反應終了後,將反應液予以減壓濃縮,以二乙基醚100ml萃取2次,減壓濃縮而得含目的物之粗生成物2.49g。將其中之186mg以TLC薄層層析板(0.5mm薄層層析板5片、100%醋酸乙基酯)純化,分別得到化合物(1-702)47mg(產率9%)及1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基磷醯胺硫代酸二氯化物19mg(產率5%)。
(1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基)磷醯胺硫代酸二氯化物
於三氟甲烷磺酸鈉330mg(2mmol)中加入醋酸乙基酯2ml並予以攪拌,加入氧氯化磷154mg(1mmol),在室溫攪拌5分鐘。接著加入以前述之方法合成的1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞胺鹽酸鹽220mg(0.86mmol),並攪拌2小時。將反應溶液以二氧化矽膠體層析(醋酸乙基酯:己烷=1:1展開)純化,得到目的物。產量115mg(產率39%)
以依據合成例1~11之方法製造下述表中所示之化合物。
此外,表中之合成法記錄於下。
A:與合成例1同樣的方法
B:與合成例2同樣的方法
C:與合成例3同樣的方法
D:與合成例4同樣的方法
E:與合成例5同樣的方法
F:與合成例6同樣的方法
G:與合成例7、8同樣的方法
H:與合成例9同樣的方法
將上述成分均一地混合,予以粉碎後得到水合劑。
化合物P212 10重量%
將上述成分均一地粉碎混合,加入水充分地混練後,予以造粒乾燥而得顆粒水合劑。
將上述摻合除了三仙膠1%水溶液與適當量的水外之全量先預備混合後,以濕式粉碎機粉碎。之後,之後,加入三仙膠1%水溶液與殘餘量的水,得到100重量%之流性膠狀劑。
將上述成分均一地混合、溶解而得乳劑。
將上述成分均一地混合而得粉劑。
將上述成分均一地混合而得粉劑。
將上述成分均一地混合而得粉劑。
將上述成分均一地粉碎混合,加入水充分地混練後,予以造粒乾燥而得粒劑。
以上述成分藉由界面聚合法而於化學式(I)所示之化合物粒子與益達胺粒子之表面形成胺基甲酸酯樹脂皮膜,得到微膠囊劑。
將上述成分均一地粉碎混合,加入水充分地混練後,予以造粒乾燥而得粒劑。
將上述成分均一地粉碎混合,加入水充分地混練後,予以造粒乾燥而得粒劑。
將上述成分均一地攪拌、溶解而得液化滴劑。
將上述成分均一地混合而得液化滴劑。
將上述成分溶解,加入聚氧乙烯苯乙烯基苯基醚14重量%、十二烷基苯磺酸鈣6%,充分攪拌混合後得10%
乳劑。
於上述成分中適量地加入單油酸山梨醇酐或單月桂酸山梨醇酐或正辛酸單甘油酯或異硬脂酸單甘油酯或單正辛酸丙二醇,並加入醇或碳酸丙烯或N-甲基-2-吡咯啶酮或水,得到100重量%之液化適劑。
從盆栽栽培之結球萵苣切除直徑5.0cm之葉盤,於其中,散佈調製成50%丙酮水(加用0.05%Tween20)之規定濃度的式(I)之化合物的藥液。風乾後,於其中放飼2齡幼蟲。之後,將此置於25℃之恆溫室(16小時明期-8小時暗期)。放飼3日後觀察蟲的生死,再以下式算出死蟲率。實施2連制試驗。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
其結果顯示,藉由100ppm之莖葉處理,化合物
P212、1-20具有死蟲率80%以上的殺蟲活性。
從盆栽栽培之結球萵苣切除直徑5.0cm之葉盤,於其中,散佈調製成50%丙酮水(加用0.05%Tween20)之規定濃度的式(I)之化合物的藥液。風乾後,於其中放飼3齡幼蟲。之後,將此置於25℃之恆溫室(16小時明期-8小時暗期)。放飼3日後觀察蟲的生死,再以下式算出死蟲率。實施2連制試驗。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
其結果顯示出,藉由500ppm的莖葉處理,化合物P212、1-20具有死蟲率80%以上的殺蟲活性。
從盆栽栽培之小黃瓜切出直徑2.0cm之葉盤,於其中,散佈調製成50%丙酮水(加用0.05%Tween20)之規定濃度的式(I)之化合物的藥液。風乾後,於其中放飼1齡幼蟲。之後,將此置於25℃之恆溫室(16小時明期-8小時暗期)。放飼3日後觀察蟲的生死,再以下式算出死蟲率。實施2連制試驗。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
其結果顯示,藉由100ppm之莖葉處理,化合物
P212、1-20具有死蟲率80%以上的殺蟲活性。
對盆栽栽培之稻苗,以調製成50%丙酮水(加用0.05% Tween 20)之規定濃度的式(I)之化合物的藥液予以莖葉散佈處理。風乾後,於其中放飼2齡幼蟲。之後,置於25℃之恆溫室(16小時明期-8小時暗期)。放飼3日後觀察蟲的生死,再以下式算出死蟲率。實施2連制試驗。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
其結果顯示,藉由100ppm之莖葉處理,化合物P212、1-20具有死蟲率80%以上的殺蟲活性。
對盆栽栽培之稻苗,以調製成50%丙酮水(加用0.05% Tween 20)之規定濃度的式(I)之化合物的藥液予以莖葉散佈處理。風乾後,於其中放飼2齡幼蟲。之後,置於25℃之恆溫室(16小時明期-8小時暗期)。放飼6日後觀察蟲的生死,再以下式算出死蟲率。實施2連制試驗。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
其結果顯示,藉由100ppm之莖葉處理,化合物
P212、1-20具有死蟲率80%以上的殺蟲活性。
對盆栽栽培之稻苗,以調製成50%丙酮水(加用0.05% Tween 20)之規定濃度的式(I)之化合物的藥液予以莖葉散佈處理。風乾後,於其中放飼2齡幼蟲。之後,置於25℃之恆溫室(16小時明期-8小時暗期)。放飼4日後觀察蟲的生死,再以下式算出死蟲率。實施2連制試驗。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
其結果顯示,藉由100ppm之莖葉處理,化合物P212、1-20具有死蟲率80%以上的殺蟲活性。
對盆栽栽培之稻苗,以調製成50%丙酮水(加用0.05% Tween 20)之規定濃度的式(I)之化合物的藥液予以莖葉散佈處理。風乾後,於其中放飼2齡幼蟲。之後,置於25℃之恆溫室(16小時明期-8小時暗期)。放飼4日後觀察蟲的生死,再以下式算出死蟲率。實施2連制試驗。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
其結果顯示,藉由100ppm之莖葉處理,化合物P212
具有死蟲率80%以上的殺蟲活性。
在盆栽栽培之小黃瓜上放飼溫室粉蝨成蟲1晚,使其產卵。產卵開始1日後,去除成蟲,將此放置於25℃的恆溫室(16小時明期-8小時暗期)中。產卵結束3日後,從小黃瓜切出直徑2.0cm之葉盤,確認產卵後,於其中,散佈調製成50%丙酮水(加用0.05%Tween20)之規定濃度的式(I)之化合物的藥液。散佈後,將此放置於25℃的恆溫室(16小時明期-8小時暗期)中。散佈14日後觀察蟲的生死,再以下式算出死蟲率。實施2連制試驗。
死蟲率(%)={(產卵數-生存蟲數)/產卵數}×100
其結果顯示,藉由100ppm之莖葉處理,化合物P212具有死蟲率80%以上的高殺蟲活性。
從盆栽栽培之豌豆切出直徑2.8cm之葉盤,於其中,散佈調製成50%丙酮水(加用0.05%Tween20)之規定濃度的式(I)之化合物的藥液。風乾後,於其中放飼1齡幼蟲。之後,將此置於25℃之恆溫室(16小時明期-8小時暗期)。放飼3日後觀察蟲的生死,再以下式算出死蟲率。實施2連制試驗。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
其結果顯示出,藉由500ppm的莖葉處理,化合物P212、1-20具有死蟲率80%以上的高殺蟲活性。
於已調製成50%丙酮水(加用0.05% Tween 20)的規定濃度之式(I)之化合物的藥液中,將播種4日後的小麥苗莖葉部浸漬30秒鐘。風乾後,將此置入玻璃筒,再者,在相同的玻璃筒中放飼2隻紅鬚細綠蝽2齡幼蟲。放蟲後,於筒上蓋上蓋子,置於25℃之恆溫室。試驗中為了對小麥供水,乃從玻璃筒下供水給小麥吸。處理3日後觀察幼蟲的生死,再以下式算出死蟲率。3連制試驗。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
其結果顯示,藉由浸漬50ppm的藥液處理,化合物P212、1-20具有死蟲率80%以上的殺蟲活性。
對野外採集的蘋果幼果,散佈調製成50%丙酮水(加用0.05% Tween20)之規定濃度的式(I)之化合物的藥液。風乾後,將此置入塑膠杯中,再放飼珀椿成蟲2隻。放飼6日後觀察成蟲的生死,再以下式算出死蟲率。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
其結果顯示,藉由50ppm之莖葉處理,化合物P212
具有死蟲率80%以上的殺蟲活性。
於野外採集之成蟲背面,將以丙酮調製成規定濃度之式(I)之化合物的藥劑液1μL(/1隻)藉由微量注射器進行局部施用處理。藥劑處理後,以每1株有5隻地來將成蟲移至稻米苗,放置於25℃的恆溫室。處理48小時後,觀察成蟲的生死,再以下式算出死蟲率。實施2連制試驗。
死蟲率(%)={死亡蟲數/(生存蟲數+死亡蟲數)}×100
其結果顯示,0.5μg/隻之處理量中,化合物P212具有死蟲率80%以上的高殺蟲效果。
於在室內飼養的雌成蟲背面,將以丙酮調製成規定濃度之式(I)之化合物的藥劑液以1μL(/1隻)進行處理。藥劑處理後,以每1杯有5隻地將成蟲移往塑膠杯,放置於25℃的恆溫室。處理24小時後,觀察成蟲的苦悶狀況,並根據下式算出苦悶蟲率。實施2連制試驗。
死蟲率(%)={死蟲數/(生存蟲+死蟲數)}×100
其結果顯示,2μg/隻之處理量中,化合物P212、1-20具有死蟲率80%以上的高殺蟲效果。
對盆栽栽培之稻苗,以調製成10%丙酮水規定濃度之式(I)化合物的藥液進行土壤灌注處理。處理3日後,於其中,逐一放飼10隻斑飛蝨2齡幼蟲。之後,置於25℃之恆溫室(16小時明期-8小時暗期)。放飼3日後觀察蟲的生死,再以下式算出死蟲率。實施2連制試驗。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
其結果顯示,0.05mg/苗之處理量中,化合物P212、1-20具有死蟲率80%以上的高殺蟲活性。
對盆栽栽培之稻苗,以調製成10%丙酮水的規定濃度之式(I)化合物的藥液進行土壤灌注處理。處理3日後,於其中,逐一放飼10隻白背飛蝨2齡幼蟲。之後,置於25℃之恆溫室(16小時明期-8小時暗期)。放飼3日後觀察蟲的生死,再以下式算出死蟲率。實施2連制試驗。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
其結果顯示,0.05mg/苗之處理量中,化合物P212、1-20具有死蟲率80%以上的高殺蟲活性。
對盆栽栽培之稻苗,以調製成10%丙酮水之式(I)化合物的藥液進行土壤灌注處理。處理3日後,於其中,逐一放飼10隻鳶色飛蝨2齡幼蟲。之後,置於25℃之恆溫室(16小時明期-8小時暗期)。放飼3日後觀察蟲的生死,再以下式算出死蟲率。實施2連制試驗。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
其結果顯示,0.05mg/苗之處理量中,化合物P212、1-20具有死蟲率80%以上的高殺蟲活性。
對盆栽栽培之稻苗,以調製成10%丙酮水之式(I)化合物的藥液進行土壤灌注處理。處理2日後,於其中,逐一放飼水稻水象鼻蟲成蟲5隻。之後,置於25℃之恆溫室(16小時明期-8小時暗期)。放飼3日後觀察蟲的生死,再以下式算出死蟲率。實施2連制試驗。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
其結果顯示,0.1mg/苗之處理量中,化合物P212具有死蟲率80%以上的高殺蟲活性。
使播種48小時後的小麥苗根部,以調製成10%丙酮
水的規定濃度之本發明化合物的藥液予以處理。使其從根部吸收藥劑72小時後,於其中,逐一放飼斑飛蝨2齡幼蟲10隻。之後,置於25℃之恆溫室(16小時明期-8小時暗期)。放飼4日後觀察蟲的生死,再以下式算出死蟲率。試驗乃實施2連制。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
其結果顯示,20μg/苗之處理量中,化合物P212、1-20具有死蟲率80%以上的殺蟲活性。
參考試驗例1、3、18之結果顯示於下述之表中。
對盆栽栽培之稻苗,以調製成10%丙酮水之式(I)化合物的藥液進行土壤灌注處理。處理3日後,於稻米苗中,逐一地放飼採集自野外並於室內增殖之鳶色飛蝨2齡幼蟲10隻。之後,置於25℃之恆溫室(16小時明期-8小時暗期)。放飼6日後觀察蟲的生死,再以下式算出死蟲率。實施2連制試驗。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
又,為了比較,藉由以與上述同樣的方法對對益達胺感受性高系統的鳶色飛蝨進行試驗,表45中係顯示其結果。如表45所示,化合物P212、1-20,對感受性系統、抗藥性系統之鳶色飛蝨而言,顯示出高殺蟲效果,0.005mg/苗中之死蟲率各別為(感受性系統)100%、100%、(抗藥性系統I)95%、77%、(抗藥性系統II)100%、85%。另一方面,0.05mg/苗中之益達胺的死蟲率為(感受性系統)100%、(抗藥性系統I)38%、(抗藥性系統II)69%,即使在高藥量下,其殺蟲效果也低。由以上的結果可知,化合物P212、1-20即使是對對益達胺顯示出抗藥性之鳶色飛蝨,也具有高殺蟲效果。
此外,試驗害蟲的來源方面,抗藥性系統的鳶色飛蝨係使用2007年熊本縣內(I)及2005年福岡縣內(II)野外採集的蟲,又,益達胺感受性系統的鳶色飛蝨係使用在
鹿兒島縣內採集後,於室內長期累代飼養的蟲。
對盆栽栽培之稻苗,以調製成10%丙酮水的規定濃度之式(I)之化合物或由式(I)之化合物及下述記載的殺蟲劑所成混合物的藥液進行土壤灌注處理。放置3日後,於其中放飼2齡幼蟲。之後,置於25℃之恆溫室(16小時明期-8小時暗期)。放飼3日後觀察蟲的生死,再以下式算出死蟲率。試驗係藉由2連制來進行。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
又,藉由以下所示之科比方程式來算出沒有協同效果時的理論值,並將結果顯示於表中。
科比方程式:理論值(%)=100-(A×B)/100
(A:100-(僅只以化合物P212、化合物1-20處理時的死蟲率)
B:100-(僅只各以益達胺、芬普尼、剋安勃、賜諾殺、可尼丁、達特南、氟啶蟲胺腈、派滅淨、賽速安、氟比拉二福隆、環氧蟲啶處理時的死蟲率))
(協同效果判定方法)
與他劑混合時對斑飛蝨之殺蟲率,當超過科比方程式之理論值的情況時,判定有協同效果。
化合物P212與供試的殺蟲劑之益達胺、芬普尼、剋安勃、賜諾殺、可尼丁、達特南、氟啶蟲胺腈、派滅淨、賽速安、氟比拉二福隆、環氧蟲啶的混合劑,均顯示出超過理論值的死蟲率,可例證具有協同效果。
又,化合物1-20與供試的殺蟲劑之益達胺、芬普尼所成的混合劑,均顯示出超過理論值的死蟲率,可例證具有協同效果。
再者,化合物P212與供試的殺菌劑之烯丙苯噻唑、異噻菌胺、噻醯菌胺、肟醚菌胺的混合劑,均顯示出與單獨以化合物P212處理時同等以上的殺蟲效果,可例證能與殺菌劑進行混合處理。同樣地,化合物1-20與供試的殺菌劑烯丙苯噻唑的混合劑係顯示出與單獨以化合物1-20處理時同等以上的殺蟲效果,可例證能與殺菌劑進行混合處理。
對盆栽栽培之稻苗,以調製成50%丙酮水(加用0.05%Tween20)之規定濃度的式(I)之化合物或由式(I)之化合物及下述記載的殺蟲劑所成混合物的藥液進行莖葉散佈處理。風乾後,於其中放飼2齡幼蟲。之後,置於25℃之恆溫室(16小時明期-8小時暗期)。放飼3日後觀察蟲的生死,再以下式算出死蟲率。試驗係藉由2連制來進行。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲
數)}×100
又,藉由以下所示之科比方程式來算出沒有協同效果時的理論值,並將結果顯示於表中。
科比方程式:理論值(%)=100-(A×B)/100
(A:100-(僅只以化合物P212、化合物1-20處理時的死蟲率)
B:100-(僅只各以依芬寧、矽護芬處理時的死蟲率))
(協同效果判定方法)
與他劑混合時對斑飛蝨之殺蟲率,當超過科比方程式之理論值的情況時,判定有協同效果。
化合物P212、化合物1-20與供試的殺蟲劑之依芬寧、矽護芬的混合劑,均顯示出與理論值同等程度的死蟲率,莖葉處理的使用法中,亦可例證能與殺蟲劑混合。
從盆栽栽培之小黃瓜切出直徑2.0cm之葉盤,於其中,散佈調製成50%丙酮水(加用0.05%Tween20)之規定濃度的式(I)之化合物或由式(I)之化合物及下述記載的殺蟲劑所成混合物的藥液。風乾後,於其中放飼1齡幼蟲。之後,將此置於25℃之恆溫室(16小時明期-8小時暗期)。放飼3日後觀察蟲的生死,再以下式算出死蟲率。試驗係藉由2連制來進行。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
又,藉由以下所示之科比方程式來算出沒有協同效果時的理論值,並將結果顯示於表中。
科比方程式:理論值(%)=100-(A×B)/100
(A:100-(僅只以化合物P212、化合物1-20處理時的死蟲率)
B:100-(僅只以阿啡多片處理時的死蟲率))
(協同效果判定方法)
與他劑混合時對棉蚜的殺蟲率,當超過科比方程式之理論值的情況時,判定有協同效果。
化合物P212、化合物1-20與供試的式(II)之化合物的混合劑均顯示出超過理論值之死蟲率,可例證具有協同效果。
從盆栽栽培之結球萵苣切除直徑5.0cm之葉盤,於其中,散佈調製成50%丙酮水(加用0.05%Tween20)之規定濃度的式(I)之化合物或由式(I)之化合物及下述記載的殺蟲劑所成混合物的藥液。風乾後,於其中放飼2齡
幼蟲。之後,將此置於25℃之恆溫室(16小時明期-8小時暗期)。放飼3日後觀察蟲的生死,再以下式算出死蟲率。試驗係藉由2連制來進行。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
又,藉由以下所示之科比方程式來算出沒有協同效果時的理論值,並將結果顯示於表中。
科比方程式:理論值(%)=100-(A×B)/100
(A:100-(僅只以化合物P212處理時的死蟲率)
B:100-(僅只以氟奎因、賜諾殺、芬普尼、剋安勃、1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido〔1,2-a〕pyrimidin-1-ium-2-olate、阿啡多片處理時的死蟲率))
(協同效果判定方法)
與他劑混合時對小菜蛾的殺蟲率,當超過科比方程式之理論值的情況時,判定有協同效果。
化合物P212與供試的殺蟲劑氟奎因所成的混合劑,顯示出超過理論值之死蟲率,可例證具有協同效果。
從盆栽栽培之結球萵苣切除直徑5.0cm之葉盤,於其中,散佈調製成50%丙酮水(加用0.05%Tween20)之規定濃度的式(I)之化合物或由式(I)之化合物及下述記載的殺蟲劑所成混合物的藥液。風乾後,於其中放飼3齡幼蟲。之後,將此置於25℃之恆溫室(16小時明期-8小時暗期)。放飼3日後觀察蟲的生死,再以下式算出死蟲率。試驗係藉由2連制來進行。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
又,藉由以下所示之科比方程式來算出沒有協同效果時的理論值,並將結果顯示於表中。
科比方程式:理論值(%)=100-(A×B)/100
(A:100-(僅只以化合物P212處理時的死蟲率)
B:100-(僅只以殺蟲劑之剋安勃、因滅汀安息香酸
鹽、氟奎因或阿啡多片處理時的死蟲率))
(協同效果判定方法)
與他劑混合時對斜紋夜盗蛾的殺蟲率,當超過科比方程式之理論值的情況時,判定有協同效果。
化合物P212與供試的殺蟲劑剋安勃、因滅汀安息香酸鹽、氟奎因或阿啡多片的混合劑,顯示出超過理論值之死蟲率,可例證具有協同效果。
從盆栽栽培之豌豆切出直徑2.8cm之葉盤,於其中,散佈調製成50%丙酮水(加用0.05%Tween20)之規定濃度的式(I)之化合物或由式(I)之化合物及下述記載的殺蟲劑所成混合物的藥液。風乾後,於其中放飼1齡幼蟲。之後,將此置於25℃之恆溫室(16小時明期-8小時暗期)。放飼3日後觀察蟲的生死,再以下式算出死蟲率。試驗係藉由2連制來進行。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
又,藉由以下所示之科比方程式來算出沒有協同效果時的理論值,並將結果顯示於表中。
科比方程式:理論值(%)=100-(A×B)/100
(A:100-(僅只以化合物P212處理時的死蟲率)
B:100-(僅只以殺蟲劑之益達胺或達特南處理時的死蟲率))
(協同效果判定方法)
與他劑混合時對柑橘黃薊馬之殺蟲率,當超過科比方程式之理論值的情況時,判定有協同效果。
化合物P212與供試的殺蟲劑之益達胺或達特南的混合劑,顯示出超過理論值之死蟲率,可例證具有協同效果。
對盆栽栽培之稻苗,以調製成10%丙酮水的規定濃度之式(I)之化合物或由式(I)之化合物及下述記載的殺蟲劑所成混合物的藥液進行土壤灌注處理。放置3日後,於其中放飼2齡幼蟲。之後,置於25℃之恆溫室(16小時明期-8小時暗期)。放飼6日後觀察蟲的生死,再以下式算出死蟲率。試驗係藉由2連制來進行。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
又,藉由以下所示之科比方程式來算出沒有協同效果時的理論值,並將結果顯示於表中。
科比方程式:理論值(%)=100-(A×B)/100
(A:100-(僅只以化合物P212處理時的死蟲率)
B:100-(僅只以殺蟲劑之氰蟲醯胺、芬普尼或賜諾殺處理時的死蟲率))
(協同效果判定方法)
與他劑混合時對二化螟蟲之殺蟲效果(表),當超過
以表中所示之根據科比方程式之理論值時,判定有協同效果。
化合物P212與供試的殺蟲劑之氰蟲醯胺、芬普尼或賜諾殺的混合劑,均顯示出超過理論值的死蟲率,可例證具有協同效果。
對盆栽栽培之稻苗,以調製成10%丙酮水的規定濃度之式(I)之化合物或由式(I)之化合物及下述記載的殺蟲劑所成混合物的藥液進行土壤灌注處理。放置3日後,於其中放飼1齡幼蟲。之後,置於25℃之恆溫室(16小時明期-8小時暗期)。放飼5日後觀察蟲的生死,再以下式算出死蟲率。試驗係藉由2連制來進行。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲
數)}×100
又,藉由以下所示之科比方程式來算出沒有協同效果時的理論值,並將結果顯示於表中。
科比方程式:理論值(%)=100-(A×B)/100
(A:100-(僅只以化合物P212處理時的死蟲率)
B:100-(僅只以殺蟲劑之賜諾殺或芬普尼處理時的死蟲率))
(協同效果判定方法)
與他劑混合時對雙帶小夜蛾之殺蟲率,當超過科比方程式之理論值的情況時,判定有協同效果。
化合物P212與供試的殺蟲劑之賜諾殺或芬普尼的混合劑,均顯示出超過理論值的死蟲率,可例證具有協同效果。
將以丙酮調製成規定濃度之式(I)之化合物及下述記載的殺蟲劑,分別地局部施用處理於相同豆象成蟲的背面。之後,將豆象置入塑膠杯,放置於25℃的恆溫室(16小時明期-8小時暗期)中。放飼1日後觀察蟲的生死,再以下式算出死蟲率。試驗係藉由2連制來進行。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
又,藉由以下所示之科比方程式來算出沒有協同效果時的理論值,並將結果顯示於表中。
科比方程式:理論值(%)=100-(A×B)/100
(A:100-(僅只以化合物P212處理時的死蟲率)
B:100-(僅只以殺蟲劑芬普尼或益達胺處理時的死蟲率))
(協同效果判定方法)
與他劑混合時對豆象之殺蟲率,當超過科比方程式之
理論值的情況時,判定有協同效果。
化合物P212與供試的殺蟲劑芬普尼或益達胺之共同處理均顯示出超過理論值之死蟲率,可例證具有協同效果。
對盆栽栽培之稻苗,以藉由10%丙酮水調製成規定濃度之式(I)之化合物或由式(I)之化合物與下述記載之殺菌劑所成之混合物的藥液進行土壤灌注處理。處理3日後,於其中,噴霧接種稻熱病菌之胞子懸濁液(2×105個/mL、0.05%Tween加用),於濕室中放置24小時以促進感染。之後,置於25℃之恆溫室(16小時明期-8小時暗期)。接種7日後計測病斑數,藉由次式算出防治價。試驗係藉由3連制來進行。
防治價={(無處理區的病斑數-處理區的病斑數)/(無處理區的病斑數)}×100
其結果顯示,烯丙苯噻唑0.125mg/苗之處理量中,化合物P212、化合物1-20的任一混合劑均顯示出與以烯丙苯噻唑單獨處理時同等的殺菌效果,可例證能與殺菌劑進行混合處理。
對稻米種子,以藉由10%丙酮水調製成規定濃度之式(I)之化合物或由式(I)之化合物與下述記載之殺菌劑所成之混合物的藥液進行葉面散佈處理。處理後,於其中噴霧接種稻熱病菌之胞子懸濁液(1.5×105個/mL、0.05%Tween加用),之後,置於25℃之恆溫室(16小時明期-8小時暗期)。接種14日後計測病斑數,藉由次式算出防治價。試驗係藉由3連制來進行。
防治價={(無處理區的病斑數-處理區的病斑數)/(無處理區的病斑數)}×100
其結果顯示,0.5ppm之處理量中,化合物P212之混合劑亦顯示出與以噻醯菌胺、異噻菌胺、肟醚菌胺、三賽唑、雙氯氰菌胺、替伏素、亞托敏、春雷黴素單獨處理時同等的殺菌效果,可例證能與殺菌劑進行混合處理。
對播種6週後的稻米苗,以藉由10%丙酮水調製成規定濃度之式(I)之化合物或由式(I)之化合物與下述記載之殺菌劑所成之混合物的藥液進行莖葉散佈處理。風乾後,於其中將稻紋枯病菌之菌叢(每1.0cm2見方之寒天)靜置於稻米植株基部。之後,放置於恆溫室(晝30℃-夜25℃、16小時明期-8小時暗期)。接種6日後計測病斑高,藉由次式算出防治價。試驗乃實施2連制。
防治價={(無處理區的病斑高-處理區的病斑高)/(無處理區的病斑高)}×100
其結果顯示,在賽氟滅粒劑、福拉比、戊菌隆、亞托敏、矽氟唑、維利黴素、肟醚菌胺之5ppm的處理濃度中,與50ppm之化合物P212所成的混合劑亦顯示出與以各賽氟滅粒劑、福拉比、戊菌隆、亞托敏、矽氟唑、維利黴素、肟醚菌胺之單獨處理時同等的殺菌效果,可例證能與殺菌劑進行混合處理。
於育苗箱中播種稻米,30℃下3日進行催芽後,將育苗箱移至25℃的玻璃溫室中。於播種5日後的綠化期,以既定量的烯丙苯噻唑0.24mg/mg(24%)與化合物P212 0.02mg/mg(2%)所成之混合粒劑,對育苗箱進行處理。於播種22日後,將稻米苗移植到1/5000a之瓦氏盆中,並使其於25℃的溫室內生育。移植至瓦氏盆13、26、38日後,放飼斑飛蝨之2齡幼蟲,之後,放置於25℃之玻璃
溫室內。放飼5日後觀察蟲的生死,再以下式算出死蟲率。試驗係藉由2連制來進行。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
其結果顯示,由烯丙苯噻唑與化合物P212所成的混合粒劑,具有死蟲率100%的高殺蟲效果,可例證顯示實用的防治效果。
對盆栽栽培之稻苗,以調製成10%丙酮水的規定濃度之式(I)之化合物或由式(I)之化合物與下述記載之水稻除草劑所成之混合物的藥液進行土壤處理。放置3日後,於其中放飼2齡幼蟲。之後,置於25℃之恆溫室(16小時明期-8小時暗期)。放飼5日後觀察蟲的生死,再以下式算出死蟲率。試驗係藉由2連制來進行。
死蟲率(%)={死亡蟲數/(生存蟲數十死亡蟲數)}×100
化合物P212與供試的除草劑之唑吡嘧磺隆、唑草胺、丁基賽伏草、殺草隆、吡唑特的混合劑,均顯示出與單獨以化合物P212處理時同等以上的殺蟲效果,可例證能與除草劑進行混合處理。
於小鼠背中面黏著直徑2cm、高度2cm之膠囊。將式(I)之化合物、害獲滅、莫昔克丁、百滅寧、三亞蟎、芬普尼、賜諾特、益達胺或達特南、由式(I)之化合物與殺蟲劑之混合物,以表中所示之濃度溶解於乙醇中,再各自滴到膠囊內的小鼠體表。使其充分地乾燥後,放飼8隻長角血蜱小壁蝨,膠囊上部係蓋上蓋子予以密閉。小鼠係飼養於籠子中、25℃、12小時明期-12小時暗期之條件下。放飼5日後,取下膠囊,計測小壁蝨之生死、吸血個體數,根據次式來算出死、苦悶蟲率。
死、苦悶蟲率(%)={死、苦悶蟲數/(生存蟲數十死、苦悶蟲數)}×100
又,藉由以下所示之科比方程式來算出沒有協同效果時的理論值,並將結果顯示於表中。
科比方程式:理論值(%)=100-(A×B)/100
(A:100-(僅只以化合物P212處理時的死蟲率)
B:100-(僅只以殺蟲劑害獲滅、莫昔克丁、百滅寧、三亞蟎、芬普尼、賜諾特、益達胺或達特南處理時的死蟲率))
(協同效果判定方法)
與他劑混合時對長角血蜱之殺蟲率,當超過科比方程式之理論值的情況時,判定有協同效果。
其結果顯示,以害獲滅、莫昔克丁、百滅寧、賜諾特與化合物P212所成的任一混合劑亦顯示出與單獨處理時同等的殺壁蝨效果,可例證能與害獲滅、莫昔克丁、百滅寧或賜諾特所成的混合處理。
又,化合物P212與供試的殺蟲劑之三亞蟎、芬普尼、百利普芬、賜諾殺、益達胺或達特南之共同處理均顯示出超過理論值之死蟲率,可例證具有協同效果。
Claims (28)
- 一種有害生物防治用組成物,其係含有作為有效成分之次式(I)所示之新穎亞胺基吡啶衍生物、或該等之酸加成鹽的至少1種與其他有害生物防治劑的至少1種所成者,
- 如請求項1中記載之有害生物防治用組成物,其係含有作為有效成分之次式(Ia)所示之胺衍生物、或該等之酸加成鹽的至少1種與其他有害生物防治劑的至少1種所成者,
- 如請求項1中記載之有害生物防治用組成物,其中,Ar係6-氯-3-吡啶基、6-氯-5-氟-3-吡啶基、6-氟-3-吡啶基、6-溴-3-吡啶基、2-氯-5-嘧啶基。
- 如請求項1或3中記載之有害生物防治用組成物,其中,式(I)中之A係次式(A-1),且Y係氫原子、鹵素原子、氰基,
- 如請求項1、或3~4中任一項記載之有害生物防治用組成物,其中,式(I)中之R係式(c)之基,
- 如請求項1、或3~4中任一項記載之有害生物防治用組成物,其中,式(I)中之R係式(a)之基,
- 如請求項1、或3~4中任一項記載之有害生物防治用組成物,其中,式(I)中之R係式(d)之基,
- 如請求項1中記載之有害生物防治用組成物,其 中,亞胺基吡啶衍生物係N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙醯胺、N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙硫醯胺、或N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟-N’-異丙基乙脒。
- 如請求項1~8中任一項記載之組成物,其係進一步含有農畜藥上可容許之擔體。
- 如請求項1~8中任一項記載之組成物,其中,其他有害生物防治劑係殺蟲劑及/或殺菌劑。
- 如請求項1~8中任一項記載之組成物,其中,其他有害生物防治劑係殺蟲劑。
- 如請求項1~9中任一項記載之組成物,其中,其他有害生物防治劑係殺蟲劑,且由包含歐殺松(acephate)、二氯松(dichlorvos)、EPN、撲滅松(fenitrothion)、芬滅松(fenamifos)、普硫松(prothiofos)、佈飛松(profenofos)、白克松(pyraclofos)、甲基毒死蜱(chlorpyrifos-methyl)、大利松(diazinon)、三氯松(trichlorfon)、四氯乙烯磷(tetrachlorvinphos)、溴酚磷(bromofenofos)、賽硫磷(cythioate)之有機磷酸酯系化合物、包含納乃得(methomy1)、硫敵克(thiodicarb)、得滅克(aldicarb)、毆殺滅(oxamyl)、安丹(propoxur)、加保利(carbaryl)、丁基滅必蝨(fenobucarb)、乙硫甲威(ethiofencarb)、芬硫克(fenothiocarb)、比加普 (pirimicarb)、加保扶(carbofuran)、免扶克(benfuracarb)之胺基甲酸酯系化合物、包含培丹(cartap)、硫賜安(thiocyclam)之沙蠶毒素衍生物、包含大克蟎(dicofol)、得脫蟎(tetradifon)之有機氯系化合物、包含丙烯菊酯(allethrin)、d.d-T-丙烯菊酯(d.d-T-allethrin)、dl.d-T80丙烯菊酯(dl.d-T80 allethrin)、除蟲菊酯(pyrethrins)、苯醚菊酯(phenothrin)、氟氯苯菊酯(flumethrin)、氟氯氰菊酯(cyfluthrin)、d.d-T80丙炔菊酯(d.d-T80 prarethrin)、胺菊酯(phthalthrin)、四氟苯菊酯(transfluthrin)、苄呋菊酯(resmethrin)、苯醚氰菊酯(cyphenothrin)、除蟲菊萃取物(pyrethrum extract)、協力靈222(synepirin222)、協力靈500(synepirin 500)、百滅寧(permethrin)、七氟菊酯(tefluthrin)、賽滅寧(cypermethrin)、第滅寧(deltamethrin)、賽洛寧(cyhalothrin)、芬化利(fenvalerate)、福化利(fluvalinate)、依芬寧(ethofenprox)、矽護芬(silafluofen)之除蟲菊酯系化合物、包含二福隆(diflubenzuron)、得福隆(teflubenzuron)、氟芬隆(flufenoxuron)、克福隆(chlorfluazuron)、祿芬隆(lufenuron)之苯甲醯基尿素系化合物、包含烯蟲丙酯(methoprene)之保幼激素樣化合物、包含可芬諾之脫皮激素樣化合物、布芬淨(buprofezin)、合賽多(hexythiazox)、三亞蟎(amitraz)、克死蟎 (chlordimeform)、畢達本(pyridaben)、芬普蟎(fenpyroxymate)、畢汰芬(pyrimidifen)、得芬瑞(tebufenpyrad)、脫芬瑞(tolfenpyrad)、亞醌蟎(acequinocyl)、賽芬蟎(cyflumetofen)、氟大滅(flubendizmide)、益斯普(ethiprole)、芬普尼(fipronil)、乙蟎唑(etoxazole)、益達胺(imidacloprid)、可尼丁(clothianidin)、賽速安(thiamethoxam)、亞滅培(acetamiprid)、烯啶蟲胺(nitenpyram)、賽果培(thiacloprid)、達特南(dinotefuran)、派滅淨(pymetrozine)、必芬蟎(bifenazate)、賜派芬(spirodiclofen)、螺甲蟎酯(spiromesifen)、賜派滅(spirotetramat)、氟尼胺(flonicamid)、克凡派(chlorfenapyr)、百利普芬(pyriproxyfen)、因得克(indoxacarb)、三氟甲吡醚(pyridalyl)、賜諾殺(spinosad)、賜諾特(spinetoram)、阿巴汀(avermectin)、倍脈心(milbemycin)、吡唑殺蟎(pyflubumide)、賽必芬蟎(cyenopyrafen)、百利氟松(pyrifluquinazon)、剋安勃(chlorantraniliprole)、氰蟲醯胺(cyantraniliprole)、雷皮菌素(lepimectin)、美氟綜(metaflumizone)、必拉氟勃(pyrafluprole)、必利勃(pyriprole)、愛美松(hydramethylnon)、唑蚜威(triazamate)、氟啶蟲胺腈(sulfoxaflor)、氟比拉二福隆(flupyradifurone)、氟奎因(flometoquin)、害獲滅 (ivermectin)、司拉克丁(selamectin)、莫昔克丁(moxidectin)、多拉克丁(doramectin)、依普立諾克丁(eprinomectin)、倍脈心肟(milbemycin oxime)、避蚊胺(deet)、噁蟲酮(metoxadiazone)、賽滅淨(cyromazine)、氟幼靈(triflumuron)、大茴香油(star anise oil)、三氯苯達唑(triclabendazole)、氟苯達唑(flubendazole)、芬苯達唑(fenbendazole)、葡萄糖酸銻鈉(antimony sodium gluconate)、鹽酸左旋咪唑(levamisole hydrochloride)、雙硫酸醇(bithionol)、二氯酚(dichlorophen)、酚噻嗪(phenothiazine)、二硫化碳哌嗪(piperazine carbon disulfide)、磷酸哌嗪(piperazine phosphate)、己二酸哌嗪(piperazine adipate)、檸檬酸哌嗪(piperazine citrate)、美拉索明二鹽酸鹽(melarsomine dihydrochloride)、美替立啶(metyridine)、茴蒿素(santonin)、羥萘酸吡喃泰(pyrantel pamoate)、吡喃泰(pyrantel)、帕芝奎(praziquantel)、苯硫胍(febantel)、艾默德斯(emodepside)、因滅汀安息香酸鹽(emamectin benzoate)、環氧蟲啶(Cycloxaprid)、1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido〔1,2-a〕pyrimidin-1-ium-2-olate、有機金屬系化合物、二硝基系化合物、有機硫化合物、尿素系化合物、三嗪系化合物、聯胺系化合物、及次式(II)所示之化合物、或該等之農畜藥上可容許之酸加成鹽所成之群選出的殺蟲 劑,
- 如請求項1~9中任一項記載之組成物,其中,其他有害生物防治劑係殺菌劑,且由包含亞托敏(azoxystrobin)、肟醚菌胺(orysastrobin)、克收欣(kresoxym-methyl)、三氟敏(trifloxystrobin)之甲氧丙烯酸酯系化合物、包含滅派林(mepanipyrim)、派美尼(pyrimethanil)、賽普洛(cyprodinil)之苯胺嘧啶系化合物、包含三泰芬(triadimefon)、比多農(bitertanol)、三氟菌唑(triflumizole)、乙環唑(etaconazole)、普克利(propiconazole)、平克唑(penconazole)、護矽得(flusilazole)、腈菌唑(myclobutanil)、環唑醇(cyproconazole)、戊唑醇(tebuconazole)、菲克利(hexaconazole)、撲克拉(prochloraz)、矽氟唑(simeconazole)之唑系化合物、 包含滅蟎猛(quinomethionate)之喹喔啉系化合物、包含代森錳(maneb)、代森鋅(zineb)、代森錳鋅(mancozeb)、聚胺基甲酸酯(polycarbamate)、丙森鋅(propineb)之二硫代胺基甲酸酯系化合物、包含乙霉威(diethofencarb)之苯基胺基甲酸酯系化合物、包含四氯異苯腈(chlorothalonil)、五氯硝基苯(quintozene)之有機氯系化合物、包含免賴得(benomyl)、甲基多保淨(thiophanate-methyl)、卡苯達唑(carbendazole)之苯咪唑系化合物、包含滅達樂(metalaxyl)、毆殺斯(oxadixyl)、歐呋醯胺(ofurase)、本達樂(benalaxyl)、呋霜靈(furalaxyl)、酯菌胺(cyprofuram)之苯基醯胺系化合物、包含苯氟磺胺(dichlofluanid)之次磺酸系化合物、包含氫氧化銅(II)(copper hydroxide)、羥基喹啉銅(oxine-copper)之銅系化合物、包含羥基異噁唑(hydroxyisoxazole)之異噁唑系化合物、包含三乙膦酸鋁(fosetyl-aluminium)、甲基立枯磷(tolclofos-methyl)之有機磷系化合物、包含卡丹(captan)、四氯丹(captafol)、滅菌丹(folpet)之N-鹵基硫代烷基系化合物、包含撲滅寧(procymidone)、依普同(iprodione)、免克寧(vinchlozolin)之二羧基醯亞胺系化合物、包含賽氟滅粒劑(thifluzamide)、福拉比(furametpyr)、福多寧(flutolanil)、滅普寧(mepronil)之苯甲醯苯胺系化合物、包含芬普福 (fenpropimorph)、達滅芬(dimethomorph)之嗎啉系化合物、包含氫氧化三苯基錫(fenthin hydroxide)、醋酸三苯基錫(fenthin acetate)之有機錫系化合物、包含護汰寧(fludioxonil)、拌種咯(fenpiclonil)之氰基吡咯系化合物、包含苯并噻二唑S甲基(acibenzolar-S-methyl)、異噻菌胺(isotianil)、噻醯菌胺(tiadinil)、加普胺(carpropamid)、雙氯氰菌胺(diclocymet)、芬諾尼(fenoxanil)、三賽唑(tricyclazole)、百快隆(pyroquilon)、富米綜(ferimzone)、熱必斯(fthalide)、扶吉胺(fluazinam)、克絕(cymoxanil)、賽福寧(triforine)、比芬諾(pyrifenox)、烯丙苯噻唑(probenazole)、芬瑞莫(fenarimol)、苯鏽啶(fenpropidin)、戊菌隆(pencycuron)、賽座滅(cyazofamid)、異丙菌胺(iprovalicarb)、替伏素(tebufloquin)、異丙基苯噻菌胺(benthiavalicarb-isopropyl)、脫普洛卡(tolprocarb)、維利黴素(validamycin)、春雷黴素(Kasugamycin)、鏈黴素(Streptomycin)、UK-2A類之9員環二內酯化合物、次式(III)所示之化合物、次式(IV)所示之化合物、及次式(V)所示之化合物、或該等之農畜藥上可容許之酸加成鹽所成之群選出的殺菌劑,
- 如請求項1~9中任一項記載之組成物,其中,其他有害生物防治劑係殺蟲劑,且為百滅寧(permethrin)、益達胺(imidacloprid)、可尼丁(clothianidin)、達特南(dinotefuran)、賽果培(thiacloprid)、賽速安(thiamethoxam)、派滅淨(pymetrozine)、賜諾殺(spinosad)、賜諾特(spinetoram)、芬普尼(fipronil)、剋安勃(chlorantraniliprole)、氰蟲醯胺(cyantraniliprole)、依芬寧(ethofenprox)、矽護芬(silafluofen)、三亞蟎(amitraz)、益斯普(ethiprole)、氟尼胺(flonicamid)、氟啶蟲胺腈(sulfoxaflor)、氟比拉二福隆(flupyradifurone)、氟奎因(flometoquin)、害獲滅(ivermectin)、莫昔克丁(moxidectin)、因滅汀安息香酸鹽(emamectin benzoate)、環氧蟲啶 (Cycloxaprid)、1-((6-chloropyridin-3-yl)methyl)-4-oxo-3-phenyl-4H-pyrido〔1,2-a〕pyrimidin-1-ium-2-olate、及阿啡多片(afidopyropen)、或該等之農畜藥上可容許之酸加成鹽所成之群選出的殺蟲劑。
- 如請求項1~9中任一項記載之組成物,其中,其他有害生物防治劑係殺菌劑,且為亞托敏(azoxystrobin)、肟醚菌胺(orysastrobin)、賽氟滅粒劑(thifluzamide)、福拉比(furametpyr)、熱必斯(fthalide)、烯丙苯噻唑(probenazole)、苯并噻二唑S甲基(acibenzolar-S-methyl)、噻醯菌胺(tiadinil)、異噻菌胺(isotianil)、加普胺(carpropamid)、雙氯氰菌胺(diclocymet)、芬諾尼(fenoxanil)、三賽唑(tricyclazole)、百快隆(pyroquilon)、富米綜(ferimzone)、替伏素(tebufloquin)、矽氟唑(simeconazole)、維利黴素(validamycin)、春雷黴素(Kasugamycin)、戊菌隆(pencycuron)所成之群選出的殺菌劑。
- 一種組合物,其係含有N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙醯胺或其酸加成鹽、N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙硫醯胺或其酸加成鹽、或N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟-N’-異丙基乙脒或其酸加成鹽之亞胺基 吡啶衍生物與其他有害生物防治劑的至少1種所成者。
- 一種自有害生物保護有用植物或動物之方法,其係將N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙醯胺或其酸加成鹽、N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙硫醯胺或其酸加成鹽、或N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟-N’-異丙基乙脒或其酸加成鹽之亞胺基吡啶衍生物與其他有害生物防治劑的至少1種,同時或各別地施用於應處理之區域所成者。
- 一種自有害生物保護有用植物或動物之方法,其係將如請求項1~15中任一項記載之有害生物防治用組成物的有效量處理至作為施用對象之有害生物、有用植物、有用植物的種子、土壤、栽培擔體或動物。
- 一種自有害生物保護有用植物或動物之方法,其係將如請求項16中記載之組合物施用於作為施用對象之有害生物、有用植物、有用植物的種子、土壤、栽培擔體或動物。
- 一種如請求項1~15中任一項記載之有害生物防治用組成物的使用,其係為了自有害生物保護有用植物之使用。
- 一種如請求項16中記載之組合物的使用,其係為了自有害生物保護有用植物之使用。
- 如請求項1~8中任一項記載之組成物,其中,其他有害生物防治劑係動物寄生性害蟲防治劑。
- 如請求項22中記載之組成物,其中,其他有害生物防治劑係動物寄生性害蟲防治劑,且為包含二氯松(dichlorvos)、EPN、撲滅松(fenitrothion)、芬滅松(fenamifos)、普硫松(prothiofos)、佈飛松(profenofos)、白克松(pyraclofos)、甲基毒死蜱(chlorpyrifos-methyl)、大利松(diazinon)、三氯松(trichlorfon)、四氯乙烯磷(tetrachlorvinphos)、溴酚磷(bromofenofos)、賽硫磷(cythioate)、芬殺松(fenthion)之有機磷酸酯系化合物、包含納乃得(methomy1)、硫敵克(thiodicarb)、得滅克(aldicarb)、毆殺滅(oxamyl)、安丹(propoxur)、加保利(carbaryl)、丁基滅必蝨(fenobucarb)、乙硫甲威(ethiofencarb)、芬硫克(fenothiocarb)、比加普(pirimicarb)、加保扶(carbofuran)、免扶克(benfuracarb)之胺基甲酸酯系化合物、包含培丹(cartap)、硫賜安(thiocyclam)之沙蠶毒素衍生物、包含大克蟎(dicofol)、得脫蟎(tetradifon)之有機氯系化合物、包含丙烯菊酯(allethrin)、d.d-T-丙烯菊酯(d.d-T-allethrin)、dl.d-T80丙烯菊酯(dl.d-T80 allethrin)、除蟲菊酯(pyrethrins)、苯醚菊酯(phenothrin)、氟氯苯菊酯(flumethrin)、氟氯氰菊酯(cyfluthrin)、d.d-T80丙炔菊酯(d.d-T80 prarethrin)、胺菊酯(phthalthrin)、四氟苯菊酯(transfluthrin)、苄呋菊酯(resmethrin)、苯醚氰菊酯(cyphenothrin)、除蟲菊萃取物(pyrethrum extract)、協力靈222(synepirin222)、協力靈500(synepirin 500)、百滅寧(permethrin)、七氟菊酯(tefluthrin)、賽滅寧(cypermethrin)、第滅寧(deltamethrin)、賽洛寧(cyhalothrin)、芬化利(fenvalerate)、福化利(fluvalinate)、依芬寧(ethofenprox)、矽護芬(silafluofen)之除蟲菊酯系化合物、包含二福隆(diflubenzuron)、得福隆(teflubenzuron)、氟芬隆(flufenoxuron)、克福隆(chlorfluazuron)、祿芬隆(lufenuron)之苯甲醯基尿素系化合物、包含烯蟲丙酯(methoprene)之保幼激素樣化合物、包含可芬諾之脫皮激素樣化合物、三亞蟎(amitraz)、克死蟎(chlordimeform)、芬普尼(fipronil)、乙蟎唑(etoxazole)、益達胺(imidacloprid)、可尼丁(clothianidin)、賽速安(thiamethoxam)、亞滅培(acetamiprid)、烯啶蟲胺(nitenpyram)、賽果培(thiacloprid)、達特南(dinotefuran)、賜派芬(spirodiclofen)、百利普芬(pyriproxyfen)、因得克(indoxacarb)、賜諾殺(spinosad)、賜諾特(spinetoram)、阿巴汀(avermectin)、倍脈心(milbemycin)、美氟綜(metaflumizone)、必拉氟勃(pyrafluprole)、必利勃(pyriprole)、愛美松 (hydramethylnon)、唑蚜威(triazamate)、氟啶蟲胺腈(sulfoxaflor)、氟比拉二福隆(flupyradifurone)、害獲滅(ivermectin)、司拉克丁(selamectin)、莫昔克丁(moxidectin)、多拉克丁(doramectin)、依普立諾克丁(eprinomectin)、倍脈心肟(milbemycin oxime)、檸檬酸二乙碳醯嗪(diethylcarbamazine citrate)、避蚊胺(deet)、噁蟲酮(metoxadiazone)、賽滅淨(cyromazine)、氟幼靈(triflumuron)、大茴香油(star anise oil)、三氯苯達唑(triclabendazole)、氟苯達唑(flubendazole)、芬苯達唑(fenbendazole)、葡萄糖酸銻鈉(antimony sodium gluconate)、鹽酸左旋咪唑(levamisole hydrochloride)、雙硫酸醇(bithionol)、二氯酚(dichlorophen)、酚噻嗪(phenothiazine)、二硫化碳哌嗪(piperazine carbon disulfide)、磷酸哌嗪(piperazine phosphate)、己二酸哌嗪(piperazine adipate)、檸檬酸哌嗪(piperazine citrate)、美拉索明二鹽酸鹽(melarsomine dihydrochloride)、美替立啶(metyridine)、茴蒿素(santonin)、羥萘酸吡喃泰(pyrantel pamoate)、吡喃泰(pyrantel)、帕芝奎(praziquantel)、苯硫胍(febantel)、艾默德斯(emodepside)、得曲恩特(derquantel)、蒙內龐特(monepantel)、因滅汀安息香酸鹽(emamectin benzoate)、環氧蟲啶(Cycloxaprid)、或該等之農畜藥上可容許之酸加成鹽所成之群選出的動物寄生性害蟲防治 劑。
- 如請求項22或23中記載之組成物,其中,其他有害生物防治劑係動物寄生性害蟲防治劑,且為氟氯苯菊酯(flumethrin)、百滅寧(permethrin)、芬普尼(fipronil)、必利勃(pyriprole)、益達胺(imidacloprid)、賽速安(thiamethoxam)、亞滅培(acetamiprid)、達特南(dinotefuran)、三亞蟎(amitraz)、美氟綜(metaflumizon)、百利普芬(pyriproxyfen)、撲滅松(fenitrothion)、祿芬隆(lufenuron)、乙蟎唑(ethoxazol)、賜諾殺(spinosad)、賜諾特(spinetoram)、艾默德斯(emodepside)、因滅汀安息香酸鹽、害獲滅(ivermectin)、司拉克丁(selamectin)、莫昔克丁(moxidectin)、多拉克丁(doramectin)、依普立諾克丁(eprinomectin)、得曲恩特(derquantel)、蒙內龐特(monepantel)、或該等之農畜藥上可容許之酸加成鹽所成之群選出的動物寄生性害蟲防治劑。
- 一種組合物,其係含有N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙醯胺或其酸加成鹽、N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙硫醯胺或其酸加成鹽、或N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟-N’-異丙基乙脒或其酸加成鹽之亞胺基 吡啶衍生物與其他動物寄生性害蟲防治劑的至少1種所成者。
- 一種自有害生物保護動物之方法,其係含有將N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙醯胺或其酸加成鹽、N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟乙硫醯胺或其酸加成鹽、或N-〔1-((6-氯吡啶-3-基)甲基)吡啶-2(1H)-亞基〕-2,2,2-三氟-N’-異丙基乙脒或其酸加成鹽之亞胺基吡啶衍生物與其他動物寄生性害蟲防治劑的至少1種同時或各別地施用於應處理之區域。
- 一種如請求項1~15及請求項22~24中任一項記載之有害生物防治用組成物的使用,其係為了自有害生物保護動物之使用。
- 一種如請求項25中記載之組合物的使用,其係為了自有害生物保護動物之使用。
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