TWI821664B - 雜芳基唑化合物及有害生物防除劑 - Google Patents
雜芳基唑化合物及有害生物防除劑 Download PDFInfo
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- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000003744 tubulin modulator Substances 0.000 description 1
- 229940040064 ubiquinol Drugs 0.000 description 1
- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 239000002435 venom Substances 0.000 description 1
- 210000001048 venom Anatomy 0.000 description 1
- 231100000611 venom Toxicity 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 description 1
- 229960004740 voriconazole Drugs 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000005019 zein Substances 0.000 description 1
- 229940093612 zein Drugs 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
- HANCUBNDHABGSE-UHFFFAOYSA-L zinc;oxolane;dichloride Chemical compound [Cl-].[Cl-].[Zn+2].C1CCOC1 HANCUBNDHABGSE-UHFFFAOYSA-L 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
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- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/12—Powders or granules
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P7/00—Arthropodicides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
本發明之課題在於提供一種有害生物防除活性、其中尤其殺蟲活性及/或殺蟎活性優異,安全性優異,且工業上可有利地合成之雜芳基唑化合物。
本發明之化合物係式(I)所表示之化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物或該等之鹽。
式(I)中,
A為CH或氮原子;
B1
為CX1
或氮原子;
X1
、X2
及X3
分別獨立為氫原子、經取代或未經取代之C1~6烷基、經取代或未經取代之C2~6烯基等;
R1
為經取代或未經取代之C1~6烷基硫基、經取代或未經取代之C1~6烷基亞磺醯基等;
R2
為經取代或未經取代之C1~6烷基;
R為經取代或未經取代之C1~6烷基。
Description
本發明係關於一種雜芳基唑化合物及有害生物防除劑。更詳細而言,本發明係關於一種具有優異之殺蟲活性及/或殺蟎活性、安全性優異、且工業上可有利地合成之雜芳基唑化合物以及含有其作為有效成分之有害生物防除劑。本申請案係對於2018年10月2日提出申請之日本專利申請第2018-187675號、及於2018年10月29日提出申請之日本專利申請第2018-202997號主張優先權,並將其內容援用至本文中。
已提出有各種具有殺蟲、殺蟎活性之化合物。為了將此種化合物實際用作農藥,不僅要求效力充分高,並且要求不易產生抗藥性,不會對植物產生藥害或引起土壤污染,及對家畜或魚類等之毒性較低等。
且說,專利文獻1中揭示有式(A)或(B)所表示之化合物等。
[化1]
[化2]
又,專利文獻2中揭示有式(C)所表示之化合物等。
[化3]
[先前技術文獻]
[專利文獻]
專利文獻1:WO2017/104741A
專利文獻2:WO2018/052035A
[發明所欲解決之問題]
本發明之課題在於提供一種有害生物防除活性、其中尤其是殺蟲活性及/或殺蟎活性優異,安全性優異,且工業上可有利地合成之雜芳基唑化合物。本發明之另一課題在於提供一種含有雜芳基唑化合物作為有效成分之有害生物防除劑、殺蟲或殺蟎劑、外部寄生蟲防除劑、或者內部寄生蟲防除或驅除劑。
[解決問題之技術手段]
為了解決上述課題,經過努力研究,最終完成包含以下形態之本發明。
[1]一種化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物或該等之鹽,該化合物係以式(I)表示。
[化4]
式(I)中,
A為CH或氮原子。
B1
為CX1
或氮原子。
X1
、X2
及X3
分別獨立為氫原子、經取代或未經取代之C1~6烷基、經取代或未經取代之C2~6烯基、經取代或未經取代之C2~6炔基、羥基、經取代或未經取代之C1~6烷氧基、經取代或未經取代之C1~6烷氧基羰基、甲醯基、經取代或未經取代之C1~6烷基硫基、經取代或未經取代之C1~6烷基亞磺醯基、經取代或未經取代之C1~6烷基磺醯基、經取代或未經取代之C3~8環烷基、經取代或未經取代之C6~10芳基、經取代或未經取代之3~6員雜環基、經取代或未經取代之C6~10芳氧基、經取代或未經取代之5~6員雜芳氧基、經取代或未經取代之胺基、經取代或未經取代之胺基羰基、經取代或未經取代之肼基、硝基、氰基、鹵素基、式:-CR3
=N-OR4
所表示之基、式:-N=CHNR5
R6
所表示之基、或式:-N=S(O)q
R7
R8
所表示之基。
R3
及R4
分別獨立為氫原子、C1~6烷基、或C1~6鹵烷基。
R5
、R6
、R7
及R8
為C1~6烷基。
q為0或1。
R1
為經取代或未經取代之C1~6烷基硫基、經取代或未經取代之C1~6烷基亞磺醯基、或者經取代或未經取代之C1~6烷基磺醯基。
R2
為經取代或未經取代之C1~6烷基。
R為經取代或未經取代之C1~6烷基。
[2]如上述[1]記載之化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物或該等之鹽,其中式(I)為式(II)。
[化5]
式(II)中,
R1
、R2
及R表示與式(I)中之該等相同之含義。
X為經取代或未經取代之C1~6烷基、經取代或未經取代之C2~6烯基、經取代或未經取代之C2~6炔基、羥基、經取代或未經取代之C1~6烷氧基、經取代或未經取代之C1~6烷氧基羰基、甲醯基、經取代或未經取代之C1~6烷基硫基、經取代或未經取代之C1~6烷基亞磺醯基、經取代或未經取代之C1~6烷基磺醯基、經取代或未經取代之C3~8環烷基、經取代或未經取代之C6~10芳基、經取代或未經取代之3~6員雜環基、經取代或未經取代之C6~10芳氧基、經取代或未經取代之5~6員雜芳氧基、經取代或未經取代之胺基、經取代或未經取代之胺基羰基、經取代或未經取代之肼基、硝基、氰基、鹵素基、式:-CR3
=N-OR4
所表示之基、式:-N=CHNR5
R6
所表示之基、或式:-N=S(O)q
R7
R8
所表示之基。
R3
及R4
分別獨立為氫原子、C1~6烷基、或C1~6鹵烷基。
R5
、R6
、R7
及R8
為C1~6烷基。
q為0或1。
n表示化學上容許之X之個數,且為0~3之任一整數,n為2以上時X相互可相同亦可不同。
[3]如上述[1]記載之化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物或該等之鹽,其中式(I)為式(III)。
[化6]
式(III)中,
A、R1
、R2
及R表示與式(I)中之該等相同之含義。
X表示與式(II)中之該等相同之含義。
[4]如上述[1]記載之化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物或該等之鹽,其中於式(I)中,R為C1~6鹵烷基。
[5]一種有害生物防除劑,其含有選自由如上述[1]至[4]記載之化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物及該等之鹽所組成之群中之至少一種作為有效成分。
[6]一種殺蟲或殺蟎劑,其含有選自由如上述[1]至[4]記載之化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物及該等之鹽所組成之群中之至少一種作為有效成分。
[7]一種外部寄生蟲防除劑,其含有選自由如上述[1]至[4]記載之化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物及該等之鹽所組成之群中之至少一種作為有效成分。
[8]一種內部寄生蟲防除劑或驅除劑,其含有選自由如上述[1]至[4]記載之化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物及該等之鹽所組成之群中之至少一種作為有效成分。
[9]一種種子處理劑或營養繁殖器官處理劑,其含有選自由如上述[1]至[4]記載之化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物及該等之鹽所組成之群中之至少一種作為有效成分。
[10]一種水稻育苗箱處理用農藥粒狀組成劑,其含有選自由如上述[1]至[4]記載之化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物及該等之鹽所組成之群中之至少一種作為有效成分。
[11]一種土壤處理劑,其含有選自由如上述[1]至[4]記載之化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物及該等之鹽所組成之群中之至少一種作為有效成分。
[12]一種餌劑,其含有選自由如上述[1]至[4]記載之化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物及該等之鹽所組成之群中之至少一種作為有效成分。
[13]一種植物生長促進劑,其含有選自由如上述[1]至[4]記載之化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物及該等之鹽所組成之群中之至少一種作為有效成分。
[發明之效果]
本發明之雜芳基唑化合物可防除於農作物或衛生方面成為問題之有害生物。尤其可以更低濃度有效地防除農業害蟲及蟎類。進而,可有效地防除危害人畜之外部寄生蟲及內部寄生蟲。
[雜芳基唑化合物]
本發明之雜芳基唑化合物係式(I)所表示之化合物(以下有時記為化合物(I))、其N-氧化物化合物、立體異構物、互變異構物、水合物或該等之鹽。式(I)所表示之化合物包括作為鏡像異構物或非鏡像異構物之全部之立體異構物。
[化7]
於本發明中,用語「未經取代(unsubstituted)」意指僅為成為母核之基。於僅記載成為母核之基之名稱而無「經取代」之記載時,只要無特別說明,則意指「未經取代」。
另一方面,用語「經取代(substituted)」意指成為母核之基之任一氫原子被結構與母核相同或不同之基(取代基)取代。因此,「取代基」係鍵結於成為母核之基上之其他基。取代基可為1個,亦可為2個以上。2個以上之取代基可相同亦可不同。
用語「C1~6」等表示成為母核之基之碳原子數為1~6個等。該碳原子數不包括取代基中所存在之碳原子之數。例如具有乙氧基作為取代基之丁基屬於C2烷氧基C4烷基。
「取代基」只要為化學上所容許且具有本發明之效果,則並無特別限制。以下,例示可成為「取代基」之基。
甲基、乙基、正丙基、異丙基、正丁基、第二丁基、異丁基、第三丁基、正戊基、正己基等C1~6烷基;
乙烯基、1-丙烯基、2-丙烯基(烯丙基)、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基等C2~6烯基;
乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基等C2~6炔基;
環丙基、環丁基、環戊基、環己基、立方烷基(cubanyl group)等C3~8環烷基;
苯基、萘基等C6~10芳基;
苄基、苯乙基等C6~10芳基C1~6烷基;
3~6員雜環基;
3~6員雜環基C1~6烷基;
羥基;
甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、第二丁氧基、異丁氧基、第三丁氧基等C1~6烷氧基;
乙烯氧基、烯丙氧基、丙烯氧基、丁烯氧基等C2~6烯氧基;
乙炔氧基、炔丙氧基等C2~6炔氧基;
苯氧基、萘氧基等C6~10芳氧基;
苄氧基、苯乙氧基等C6~10芳基C1~6烷氧基;
噻唑氧基、吡啶氧基等5~6員雜芳氧基;
噻唑基甲氧基、吡啶基甲氧基等5~6員雜芳基C1~6烷氧基;
甲醯基;
乙醯基、丙醯基等C1~6烷基羰基;
甲醯氧基;
乙醯氧基、丙醯氧基等C1~6烷基羰氧基;
苯甲醯基等C6~10芳基羰基;
甲氧基羰基、乙氧基羰基、正丙氧基羰基、異丙氧基羰基、正丁氧基羰基、第三丁氧基羰基等C1~6烷氧基羰基;
甲氧基羰氧基、乙氧基羰氧基、正丙氧基羰氧基、異丙氧基羰氧基、正丁氧基羰氧基、第三丁氧基羰氧基等C1~6烷氧基羰氧基;
羧基;
氟基、氯基、溴基、碘基等鹵素基;
氟甲基、二氟甲基、三氟甲基、2,2,2-三氟乙基、五氟乙基、3,3,3-三氟丙基、2,2,3,3,3-五氟丙基、全氟丙基、2,2,2-三氟-1-三氟甲基乙基、全氟異丙基、4-氟丁基、2,2,3,3,4,4,4-七氟丁基、全氟丁基、全氟戊基、全氟己基、氯甲基、溴甲基、二氯甲基、二溴甲基、三氯甲基、三溴甲基、1-氯乙基、2,2,2-三氯乙基、4-氯丁基、全氯己基、2,4,6-三氯己基等C1~6鹵烷基;
2-氯-1-丙烯基、2-氟-1-丁烯基等C2~6鹵烯基;
4,4-二氯-1-丁炔基、4-氟-1-戊炔基、5-溴-2-戊炔基等C2~6鹵炔基;
三氟甲氧基、2-氯正丙氧基、2,3-二氯丁氧基等C1~6鹵烷氧基;
2-氯丙烯氧基、3-溴丁烯氧基等C2~6鹵烯氧基;
氯乙醯基、三氟乙醯基、三氯乙醯基等C1~6鹵烷基羰基;
胺基;
甲基胺基、二甲基胺基、二乙基胺基等C1~6烷基取代胺基;
苯胺基、萘基胺基等C6~10芳基胺基;
苄基胺基、苯乙基胺基等C6~10芳基C1~6烷基胺基;
甲醯基胺基;
乙醯基胺基、丙醯基胺基、丁醯基胺基、異丙基羰基胺基等C1~6烷基羰基胺基;
甲氧基羰基胺基、乙氧基羰基胺基、正丙氧基羰基胺基、異丙氧基羰基胺基等C1~6烷氧基羰基胺基;
胺基羰基、二甲基胺基羰基、苯基胺基羰基、N-苯基-N-甲基胺基羰基等未經取代或具有取代基之胺基羰基;
亞胺基甲基、(1-亞胺基)乙基、(1-亞胺基)正丙基等亞胺基C1~6烷基;
N-羥基亞胺基甲基、(1-(N-羥基)亞胺基)乙基、(1-(N-羥基)亞胺基)丙基、N-甲氧基亞胺基甲基、(1-(N-甲氧基)亞胺基)乙基等經取代或未經取代之N-羥基亞胺基C1~6烷基;
甲氧基亞胺基、乙氧基亞胺基、正丙氧基亞胺基、異丙氧基亞胺基、正丁氧基亞胺基等C1~6烷氧基亞胺基;
胺基羰氧基;
乙基胺基羰氧基、二甲基胺基羰氧基等C1~6烷基取代胺基羰氧基;
巰基;
甲基硫基、乙基硫基、正丙基硫基、異丙基硫基、正丁基硫基、異丁基硫基、第二丁基硫基、第三丁基硫基等C1~6烷基硫基;
三氟甲基硫基、2,2,2-三氟乙基硫基等C1~6鹵烷基硫基;
苯基硫基、萘基硫基等C6~10芳基硫基;
噻唑基硫基、吡啶基硫基等5~6員雜芳基硫基;
甲基亞磺醯基、乙基亞磺醯基、第三丁基亞磺醯基等C1~6烷基亞磺醯基;
三氟甲基亞磺醯基、2,2,2-三氟乙基亞磺醯基等C1~6鹵烷基亞磺醯基;
苯基亞磺醯基等C6~10芳基亞磺醯基;
噻唑基亞磺醯基、吡啶基亞磺醯基等5~6員雜芳基亞磺醯基;
甲基磺醯基、乙基磺醯基、第三丁基磺醯基等C1~6烷基磺醯基;
三氟甲基磺醯基、2,2,2-三氟乙基磺醯基等C1~6鹵烷基磺醯基;
苯基磺醯基等C6~10芳基磺醯基;
噻唑基磺醯基、吡啶基磺醯基等5~6員雜芳基磺醯基;
甲基磺醯氧基、乙基磺醯氧基、第三丁基磺醯氧基等C1~6烷基磺醯氧基;
三氟甲基磺醯氧基、2,2,2-三氟乙基磺醯氧基等C1~6鹵烷基磺醯氧基;
三甲基矽烷基、三乙基矽烷基、第三丁基二甲基矽烷基等三C1~6烷基取代矽烷基;
三苯基矽烷基等三C6~10芳基取代矽烷基;
氰基;硝基;
又,關於該等「取代基」,該取代基中之任一個氫原子亦可被不同結構之基取代。作為該情形時之「取代基」,可列舉:C1~6烷基、C1~6鹵烷基、C1~6烷氧基、C1~6鹵烷氧基、鹵素基、氰基、硝基等。
又,上述所謂「3~6員雜環基」係包含選自由氮原子、氧原子及硫原子所組成之群中之1~4個雜原子作為環之構成原子者。雜環基可為單環及多環中之任意者。多環雜環基只要至少一個環為雜環,其餘環可為飽和脂環、不飽和脂環或芳香環中之任意者。作為「3~6員雜環基」,可列舉:3~6員飽和雜環基、5~6員雜芳基、5~6員部分不飽和雜環基等。
作為3~6員飽和雜環基,可列舉:氮丙啶基、環氧基、吡咯啶基、四氫呋喃基、四氫噻唑基、哌啶基、哌𠯤基、嗎啉基、二氧雜環戊基、二氧雜環己基等。
作為5員雜芳基,可列舉:吡咯基、呋喃基、噻吩基、咪唑基、吡唑基、㗁唑基、異㗁唑基、噻唑基、異噻唑基、三唑基、㗁二唑基、噻二唑基、四唑基等。
作為6員雜芳基,可列舉:吡啶基、吡𠯤基、嘧啶基、嗒𠯤基、三𠯤基等。
[A]
式(I)中,A為CH或氮原子。
即,式(I)所表示之化合物為式(I-1)或式(I-2)所表示之化合物。
[化8]
[化9]
式(I-1)及式(I-2)中,B1
、R1
、R2
、R、X2
及X3
表示與式(I)中之該等相同之含義。
[B1
]
式(I)中,B1
為CX1
或氮原子。
即,式(I)所表示之化合物為式(I-3)或式(I-4)所表示之化合物。
[化10]
[化11]
式(I-3)及式(1-4)中,A、R1
、R2
、R、X2
及X3
表示與式(I)中之該等相同之含義。
式(I-3)中,X1
為氫原子、經取代或未經取代之C1~6烷基、經取代或未經取代之C2~6烯基、經取代或未經取代之C2~6炔基、羥基、經取代或未經取代之C1~6烷氧基、經取代或未經取代之C1~6烷氧基羰基、甲醯基、經取代或未經取代之C1~6烷基硫基、經取代或未經取代之C1~6烷基亞磺醯基、經取代或未經取代之C1~6烷基磺醯基、經取代或未經取代之C3~8環烷基、經取代或未經取代之C6~10芳基、經取代或未經取代之3~6員雜環基、經取代或未經取代之C6~10芳氧基、經取代或未經取代之5~6員雜芳氧基、經取代或未經取代之胺基、經取代或未經取代之胺基羰基、經取代或未經取代之肼基、硝基、氰基、鹵素基、式:-CR3
=N-OR4
所表示之基、式:-N=CHNR5
R6
所表示之基、或式:-N=S(O)q
R7
R8
所表示之基。此處,R3
及R4
分別獨立為氫原子、C1~6烷基、或C1~6鹵烷基,R5
、R6
、R7
及R8
為C1~6烷基,q為0或1。
X1
中之「C1~6烷基」可為直鏈,亦可為支鏈。作為「C1~6烷基」,可列舉:甲基、乙基、正丙基、正丁基、正戊基、正己基、異丙基、異丁基、第二丁基、第三丁基、異戊基、新戊基、2-甲基丁基、異己基等。
作為X1
中之「C1~6烷基」上之取代基,可較佳地列舉:氟基、氯基、溴基、碘基等鹵素基;氰基;乙氧基羰基等烷氧基羰基等。
作為X1
中之「C2~6烯基」,可列舉:乙烯基、1-丙烯基、2-丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基等。
作為X1
中之「C2~6炔基」,可列舉:乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、2-甲基-3-丁炔基、1-戊炔基、2-戊炔基、3-戊炔基、4-戊炔基、1-甲基-2-丁炔基、2-甲基-3-戊炔基、1-己炔基、1,1-二甲基-2-丁炔基等。
作為X1
中之「C1~6烷氧基」,可列舉:甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、第二丁氧基、異丁氧基、第三丁氧基等。
作為X1
中之「C1~6烷氧基羰基」,可列舉:甲氧基羰基、乙氧基羰基、正丙氧基羰基、異丙氧基羰基、正丁氧基羰基、第三丁氧基羰基等。
作為X1
中之「C1~6烷基硫基」,可列舉:甲基硫基、乙基硫基、正丙基硫基、正丁基硫基、正戊基硫基、正己基硫基、異丙基硫基、異丁基硫基等。
作為X1
中之「C1~6烷基亞磺醯基」,可列舉:甲基亞磺醯基、乙基亞磺醯基、第三丁基亞磺醯基等。
作為X1
中之「C1~6烷基磺醯基」,可列舉:甲基磺醯基、乙基磺醯基、第三丁基磺醯基等。
作為X1
中之「C2~6烯基」、「C2~6炔基」、「C1~6烷氧基」、「C1~6烷基硫基」、「C1~6烷基亞磺醯基」及「C1~6烷基磺醯基」上之取代基,可較佳地列舉:氟基、氯基、溴基、碘基等鹵素基;甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、第二丁氧基、異丁氧基、第三丁氧基等C1~6烷氧基。
作為X1
中之「C3~8環烷基」,可列舉:環丙基、環丁基、環戊基、環己基、立方烷基等。
作為X1
中之「C6~10芳基」,可列舉:苯基、萘基、茚基、二氫茚基、四氫萘基等。
X1
中之所謂「3~6員雜環基」係包含選自由氮原子、氧原子及硫原子所組成之群中之1~4個雜原子作為環之構成原子者。雜環基可為單環及多環中之任意者。多環雜環基只要至少一個環為雜環,其餘環可為飽和脂環、不飽和脂環或芳香環中之任意者。作為「3~6員雜環基」,可列舉:3~6員飽和雜環基、5~6員雜芳基、5~6員部分不飽和雜環基等。
作為3~6員飽和雜環基,可列舉:氮丙啶基、環氧基、吡咯啶基、四氫呋喃基、四氫噻唑基、哌啶基、哌𠯤基、嗎啉基、二氧雜環戊基、二氧雜環己基等。
作為5~6員部分不飽和雜環基,可列舉:2-氧基吡啶-1(2H)-基等。
作為5員雜芳基,可列舉:吡咯基、呋喃基、噻吩基、咪唑基、吡唑基、㗁唑基、異㗁唑基、噻唑基、異噻唑基、三唑基、㗁二唑基、噻二唑基、四唑基等。
作為6員雜芳基,可列舉:吡啶基、吡𠯤基、嘧啶基、嗒𠯤基、三𠯤基等。
作為X1
中之「C6~10芳氧基」,可列舉:苯氧基、萘氧基等。
作為X1
中之「5~6員雜芳氧基」,可列舉:吡啶氧基、嘧啶氧基等。
作為X1
中之「C3~8環烷基」、「C6~10芳基」、「3~6員雜環基」、「C6~10芳氧基」、「5~6員雜芳氧基」上之取代基,可較佳地列舉:氟基、氯基、溴基、碘基等鹵素基;甲基、乙基、正丙基、異丙基、正丁基、第二丁基、異丁基、第三丁基、正戊基、正己基等C1~6烷基;氟甲基、二氟甲基、三氟甲基、2,2,2-三氟乙基、五氟乙基、3,3,3-三氟丙基、2,2,3,3,3-五氟丙基、全氟丙基、2,2,2-三氟-1-三氟甲基乙基、全氟異丙基、4-氟丁基、2,2,3,3,4,4,4-七氟丁基、全氟丁基、全氟戊基、全氟己基、氯甲基、溴甲基、二氯甲基、二溴甲基、三氯甲基、三溴甲基、1-氯乙基、2,2,2-三氯乙基、4-氯丁基、全氯己基、2,4,6-三氯己基等C1~6鹵烷基;甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、第二丁氧基、異丁氧基、第三丁氧基等C1~6烷氧基;2-氯-正丙氧基、2,3-二氯丁氧基、三氟甲氧基等C1~6鹵烷氧基;胺基。
X1
中之「經取代或未經取代之胺基」為「-NRa
Rb
」所表示之基等。式中,Ra
及Rb
分別獨立為氫原子、C1~6烷基、C3~8環烷基、甲醯基、C1~6烷基羰基、C3~8環烷基羰基、或者經取代或未經取代之胺基羰基。
作為Ra
及Rb
中之「C1~6烷基」,可列舉與上述X1
中例示之該等相同者。
作為Ra
及Rb
中之「C3~8環烷基」,可列舉與上述X1
中例示之該等相同者。
作為Ra
及Rb
中之「C1~6烷基羰基」,可列舉:乙醯基、丙醯基等。
作為Ra
及Rb
中之「C3~8環烷基羰基」,可列舉:環丙基羰基、環丁基羰基、環戊基羰基等。
作為Ra
及Rb
中之「經取代或未經取代之胺基羰基」,可列舉:胺基羰基、甲基胺基羰基、乙基胺基羰基、二甲基胺基羰基等。
作為X1
中之「經取代或未經取代之胺基羰基」,可列舉與上述Ra
及Rb
中例示之該等相同者。
X1
中之「經取代或未經取代之肼基」為式(a)所表示之基等。
[化12]
式(a)中,*為鍵結位置,Rc
、Rd
及Re
分別獨立為氫原子、C1~6烷基、或者經取代或未經取代之苯基磺醯基等。
作為Rc
、Rd
及Re
中之「C1~6烷基」,可列舉與上述X1
中例示之該等相同者。
作為Rc
、Rd
及Re
中之「取代苯基磺醯基」,可列舉:對甲苯磺醯基等。
作為X1
中之「鹵素基」,可列舉:氟基、氯基、溴基、碘基等。
作為X1
中之「式:-CR3
=N-OR4
所表示之基」、「式:-N=CHNR5
R6
所表示之基」及「式:-N=S(O)q
R7
R8
所表示之基」之R3
、R4
、R5
、R6
、R7
及R8
中之「C1~6烷基」,可列舉與上述X1
中例示之該等相同者。
作為R3
及R4
中之「C1~6鹵烷基」,可列舉:氟甲基、二氟甲基、三氟甲基、2,2,2-三氟乙基、五氟乙基、3,3,3-三氟丙基、2,2,3,3,3-五氟丙基、全氟丙基、2,2,2-三氟-1-三氟甲基乙基、全氟異丙基、4-氟丁基、2,2,3,3,4,4,4-七氟丁基、全氟丁基、全氟戊基、全氟己基、氯甲基、溴甲基、二氯甲基、二溴甲基、三氯甲基、三溴甲基、1-氯乙基、2,2,2-三氯乙基、4-氯丁基、全氯己基、2,4,6-三氯己基等C1~6鹵烷基等。
即,式(I)所表示之化合物為式(I-5)、式(I-6)、式(I-7)或式(I-8)所表示之化合物。
[化13]
[化14]
[化15]
[化16]
式(I-5)、式(I-6)、式(I-7)及式(I-8)中,R1
、R2
、R、X2
及X3
表示與式(I)中之該等相同之含義。
式(I-5)及式(I-6)中,X1
表示與式(I-3)中之該等相同之含義。
[X2
、X3
]
X2
及X3
分別獨立為氫原子、經取代或未經取代之C1~6烷基、經取代或未經取代之C2~6烯基、經取代或未經取代之C2~6炔基、羥基、經取代或未經取代之C1~6烷氧基、經取代或未經取代之C1~6烷氧基羰基、甲醯基、經取代或未經取代之C1~6烷基硫基、經取代或未經取代之C1~6烷基亞磺醯基、經取代或未經取代之C1~6烷基磺醯基、經取代或未經取代之C3~8環烷基、經取代或未經取代之C6~10芳基、經取代或未經取代之3~6員雜環基、經取代或未經取代之C6~10芳氧基、經取代或未經取代之5~6員雜芳氧基、經取代或未經取代之胺基、經取代或未經取代之胺基羰基、經取代或未經取代之肼基、硝基、氰基、鹵素基、式:-CR3
=N-OR4
所表示之基、式:-N=CHNR5
R6
所表示之基、或式:-N=S(O)q
R7
R8
所表示之基。此處,R3
及R4
分別獨立為氫原子、C1~6烷基、或C1~6鹵烷基,R5
、R6
、R7
及R8
為C1~6烷基,q為0或1。
作為X2
及X3
中之「經取代或未經取代之C1~6烷基」、「經取代或未經取代之C2~6烯基」、「經取代或未經取代之C2~6炔基」、「經取代或未經取代之C1~6烷氧基」、「經取代或未經取代之C1~6烷氧基羰基」、「經取代或未經取代之C1~6烷基硫基」、「經取代或未經取代之C1~6烷基亞磺醯基」、「經取代或未經取代之C1~6烷基磺醯基」、「經取代或未經取代之C3~8環烷基」、「經取代或未經取代之C6~10芳基」、「經取代或未經取代之3~6員雜環基」、「經取代或未經取代之C6~10芳氧基」、「經取代或未經取代之5~6員雜芳氧基」、「經取代或未經取代之胺基」、「經取代或未經取代之胺基羰基」、「經取代或未經取代之肼基」及「鹵素基」,可列舉與上述X1
中例示之該等相同者。
式:-CR3
=N-OR4
中之R3
及R4
中之「C1~6烷基」及「C1~6鹵烷基」表示與已例示者相同之含義。
式:-N=CHNR5
R6
中之R5
及R6
中之「C1~6烷基」表示與已例示者相同之含義。
式:-N=S(O)q
R7
R8
中之R7
及R8
中之「C1~6烷基」表示與已例示者相同之含義。
[R1
]
式(I)中,R1
為經取代或未經取代之C1~6烷基硫基、經取代或未經取代之C1~6烷基亞磺醯基、或者經取代或未經取代之C1~6烷基磺醯基。
作為R1
中之「C1~6烷基硫基」、「C1~6烷基亞磺醯基」及「C1~6烷基磺醯基」,可列舉與上述X1
中例示之該等相同者。
作為R1
中之「C1~6烷基硫基」、「C1~6烷基亞磺醯基」及「C1~6烷基磺醯基」上之取代基,可較佳地列舉:氟基、氯基、溴基、碘基等鹵素基。
[R2
]
式(I)中,R2
為經取代或未經取代之C1~6烷基。
作為R2
中之「C1~6烷基」,可列舉與上述X1
中例示之該等相同者。
作為R2
中之「C1~6烷基」上之取代基,可較佳地列舉:氟基、氯基、溴基、碘基等鹵素基。
[R]
式(I)中,R為經取代或未經取代之C1~6烷基。
作為R中之「C1~6烷基」,可列舉與上述X1
中例示之該等相同者。
作為R中之「取代C1~6烷基」,可列舉:氟甲基、二氟甲基、三氟甲基、2,2,2-三氟乙基、五氟乙基、3,3,3-三氟丙基、2,2,3,3,3-五氟丙基、1-氯-2,2,3,3,3-五氟丙基、1,2,2,3,3,3-六氟丙基、全氟丙基、2,2,2-三氟-1-三氟甲基乙基、全氟異丙基、4-氟丁基、1,4,4,4-四氟丁基、2,2,3,3,4,4,4-七氟丁基、1,2,2,3,3,4,4,4-八氟丁基、全氟丁基、3,3,3-三氟-2-三氟甲基丙基、1-氯-2,3,3,3-四氟-2-三氟甲基丙基、1,2,3,3,3-五氟-2-三氟甲基丙基、2,2,3,3,4,4,5,5,5-九氟戊基、1-氯-2,2,3,3,4,4,5,5,5-九氟戊基、1,2,2,3,3,4,4,5,5,5-十氟戊基、全氟戊基、全氟己基、氯甲基、溴甲基、二氯甲基、二溴甲基、三氯甲基、三溴甲基、1-氯乙基、2,2,2-三氯乙基、4-氯丁基、全氯己基、2,4,6-三氯己基等C1~6鹵烷基;1-羥基-2,2,3,3,4,4,5,5,5-九氟戊基等羥基取代C1~6鹵烷基;1-乙醯氧基-2,2,3,3,4,4,5,5,5-九氟戊基等C1~6烷基羰氧基取代C1~6鹵烷基;(2,2,3,3,3-五氟丙氧基)甲基、(2,2,3,3,4,4,4-七氟丁氧基)甲基等C1~6鹵烷氧基C1~6烷基;((1,1,2-三氟-2-(三氟甲氧基)乙氧基)甲基等C1~6鹵烷氧基C1~6鹵烷氧基C1~6烷基。
作為R中之「C1~6烷基」上之取代基,可較佳地列舉:氟基、氯基、溴基、碘基等鹵素基;羥基;三氟甲氧基、2-氯-正丙氧基、2,3-二氯丁氧基、2,2,3,3,3-五氟丙氧基、2,2,3,3,4,4,4-七氟丁氧基等C1~6鹵烷氧基;乙醯氧基等C1~6烷基羰氧基。
[鹽]
化合物(I)之鹽只要為農園藝學上容許之鹽,則並無特別限制。作為化合物(I)之鹽,例如可列舉:鹽酸、硫酸等無機酸之鹽;乙酸、乳酸等有機酸之鹽;鋰、鈉、鉀等鹼金屬之鹽;鈣、鎂等鹼土金屬之鹽;鐵、銅等過渡金屬之鹽;三乙基胺、三丁基胺、吡啶、肼等有機鹼之鹽;銨鹽等。
[製造方法]
化合物(I)、N-氧化物化合物、立體異構物、互變異構物、水合物或該等之鹽其製造方法並無特別限定。例如該等可藉由實施例等中記載之公知之製造方法獲得。又,化合物(I)之N-氧化物化合物或鹽等可由化合物(I)藉由公知方法獲得。
[式(II)所表示之化合物]
式(I)所表示之化合物較佳為式(II)所表示之化合物。
[化17]
式(II)中,
R1
、R2
及R表示與式(I)中之該等相同之含義。
X為經取代或未經取代之C1~6烷基、經取代或未經取代之C2~6烯基、經取代或未經取代之C2~6炔基、羥基、經取代或未經取代之C1~6烷氧基、經取代或未經取代之C1~6烷氧基羰基、甲醯基、經取代或未經取代之C1~6烷基硫基、經取代或未經取代之C1~6烷基亞磺醯基、經取代或未經取代之C1~6烷基磺醯基、經取代或未經取代之C3~8環烷基、經取代或未經取代之C6~10芳基、經取代或未經取代之3~6員雜環基、經取代或未經取代之C6~10芳氧基、經取代或未經取代之5~6員雜芳氧基、經取代或未經取代之胺基、經取代或未經取代之胺基羰基、經取代或未經取代之肼基、硝基、氰基、鹵素基、式:-CR3
=N-OR4
所表示之基、式:-N=CHNR5
R6
所表示之基、或式:-N=S(O)q
R7
R8
所表示之基。
n表示化學上容許之X之個數,且為0~3之任一整數,n為2以上時X相互可相同亦可不同。
作為X中之「經取代或未經取代之C1~6烷基」、「經取代或未經取代之C2~6烯基」、「經取代或未經取代之C2~6炔基」、「經取代或未經取代之C1~6烷氧基」、「經取代或未經取代之C1~6烷氧基羰基」、「經取代或未經取代之C1~6烷基硫基」、「經取代或未經取代之C1~6烷基亞磺醯基」、「經取代或未經取代之C1~6烷基磺醯基」、「經取代或未經取代之C3~8環烷基」、「經取代或未經取代之C6~10芳基」、「經取代或未經取代之3~6員雜環基」、「經取代或未經取代之C6~10芳氧基」、「經取代或未經取代之5~6員雜芳氧基」、「經取代或未經取代之胺基」、「經取代或未經取代之胺基羰基」、「經取代或未經取代之肼基」及「鹵素基」,可列舉與上述X1
中例示之該等相同者。
式:-CR3
=N-OR4
中之R3
及R4
中之「C1~6烷基」及「C1~6鹵烷基」表示與已例示者相同之含義。
式:-N=CHNR5
R6
中之R5
及R6
中之「C1~6烷基」表示與已例示者相同之含義。
式:-N=S(O)q
R7
R8
中之R7
及R8
中之「C1~6烷基」表示與已例示者相同之含義。
式(II)中,R1
較佳為C1~6烷基磺醯基,R2
較佳為C1~6烷基。
式(II)中,R較佳為氟甲基、二氟甲基、三氟甲基、2,2,2-三氟乙基、五氟乙基、3,3,3-三氟丙基、2,2,3,3,3-五氟丙基、1-氯-2,2,3,3,3-五氟丙基、1,2,2,3,3,3-六氟丙基、全氟丙基、2,2,2-三氟-1-三氟甲基乙基、全氟異丙基、4-氟丁基、1,4,4,4-四氟丁基、2,2,3,3,4,4,4-七氟丁基、1,2,2,3,3,4,4,4-八氟丁基、全氟丁基、3,3,3-三氟-2-三氟甲基丙基、1-氯-2,3,3,3-四氟-2-三氟甲基丙基、1,2,3,3,3-五氟-2-三氟甲基丙基、2,2,3,3,4,4,5,5,5-九氟戊基、1-氯-2,2,3,3,4,4,5,5,5-九氟戊基、1,2,2,3,3,4,4,5,5,5-十氟戊基、全氟戊基、全氟己基、氯甲基、溴甲基、二氯甲基、二溴甲基、三氯甲基、三溴甲基、1-氯乙基、2,2,2-三氯乙基、4-氯丁基、全氯己基、2,4,6-三氯己基等C1~6鹵烷基,更佳為二氟甲基、三氟甲基、2,2,2-三氟乙基、五氟乙基、3,3,3-三氟丙基、2,2,3,3,3-五氟丙基、1,2,2,3,3,3-六氟丙基、全氟丙基、2,2,2-三氟-1-三氟甲基乙基、全氟異丙基、4-氟丁基、1,4,4,4-四氟丁基、2,2,3,3,4,4,4-七氟丁基、1,2,2,3,3,4,4,4-八氟丁基、全氟丁基、3,3,3-三氟-2-三氟甲基丙基、1,2,3,3,3-五氟-2-三氟甲基丙基、2,2,3,3,4,4,5,5,5-九氟戊基、1,2,2,3,3,4,4,5,5,5-十氟戊基、全氟戊基、全氟己基等C1~6氟烷基。
式(II)中,X較佳為鹵素基、經取代或未經取代之C1~6烷基、經取代或未經取代之C1~6烷氧基、甲醯基、C3~8環烷基、經取代或未經取代之C6~10芳基、經取代或未經取代之3~6員雜環基、經取代或未經取代之5~6員雜芳氧基、經取代或未經取代之胺基、或式:「-CR3
=N-OR4
」所表示之基,更佳為經取代或未經取代之C1~6烷基、C3~8環烷基、經取代或未經取代之苯基、或者經取代或未經取代之6員雜芳基,尤佳為C3~8環烷基、經取代或未經取代之苯基、或者經取代或未經取代之6員雜芳基。
式(II)中,n較佳為1。
[式(III)所表示之化合物]
式(I)所表示之化合物較佳為式(III)所表示之化合物。
[化18]
式(III)中,
A、R1
、R2
及R表示與式(I)中之該等相同之含義。
X表示與式(II)中之該等相同之含義。
式(III)中,R1
較佳為C1~6烷基磺醯基,R2
較佳為C1~6烷基,R較佳為C1~6氟烷基,X較佳為經取代或未經取代之5~6員雜芳基,更佳為經取代或未經取代之5員雜芳基。
式(I)所表示之化合物較佳為以下之化合物。
[化19]
[化20]
[化21]
[化22]
[化23]
[化24]
[化25]
[化26]
[化27]
[化28]
[化29]
[化30]
[化31]
[化32]
[化33]
[化34]
[化35]
[化36]
[化37]
[化38]
[化39]
[化40]
本發明之雜芳基唑化合物對影響植物生長之各種農業害蟲及蟎類等有害生物之防除效果優異。
又,本發明之雜芳基唑化合物由於對作物之藥害較小、且對魚類或恆溫動物之毒性低,故為安全性高之物質。因此,可用作殺蟲劑或殺蟎劑之有效成分。
進而,近年來,小菜蛾(Plutella xylostella)、浮塵子、葉蟬、油蟲等較多害蟲對各種現有藥劑之抵抗性發達,而產生該等藥劑之效力不足之問題,業界期望對於抵抗性品系之害蟲亦有效之藥劑。本發明之雜芳基唑化合物不僅對敏感性品系之害蟲有效,亦對各種抵抗性品系之害蟲、或進而殺蟎劑抵抗性品系之蟎類顯示出優異之防除效果。
本發明之雜芳基唑化合物對危害人獸之外部寄生蟲及內部寄生蟲之防除效果優異。又,由於對魚類或恆溫動物之毒性低,故為安全性高之物質。因此,可用作外部寄生蟲及內部寄生蟲之防除劑之有效成分。
又,本發明之雜芳基唑化合物於成為防除對象之生物之全部成長階段均顯示出效力,例如對蟎、昆蟲等之卵、若蟲、幼蟲、蛹、成蟲顯示出優異之防除效果。
[有害生物防除劑]
本發明之有害生物防除劑含有選自本發明之雜芳基唑化合物中之至少一種作為有效成分。關於本發明之有害生物防除劑所含之雜芳基唑化合物之量,只要顯示出有害生物之防除效果,則並無特別限制。有害生物防除劑係防除有害生物之劑,包括殺蟲或殺蟎劑、外部寄生蟲防除劑、或者內部寄生蟲防除或驅除劑等。
[殺蟲或殺蟎劑]
本發明之殺蟲或殺蟎劑含有選自本發明之雜芳基唑化合物中之至少一種作為有效成分。關於本發明之殺蟲或殺蟎劑所含之雜芳基唑化合物之量,只要顯示出殺蟲或殺蟎效果,則並無特別限制。
本發明之有害生物防除劑、或者殺蟲或殺蟎劑較佳為用於:穀物類;蔬菜類;根菜類;薯類;花卉類;果樹類;觀葉植物、茶、咖啡、可可等樹木類;牧草類;芝類;棉等植物。
於對植物施用時,本發明之有害生物防除劑、或者殺蟲或殺蟎劑可用於葉、莖、柄、花、蕾、果實、種子、芽、根、塊莖、塊根、枝條、插枝等任意部位。
又,本發明之有害生物防除劑、或者殺蟲或殺蟎劑並不特別地受所施用之植物品種限制。作為植物之品種,例如可列舉:原種、變種、改良品種、栽培品種、突變體、雜交體、基改生物(GMO)等。
本發明之有害生物防除劑可為了防除各種農業害蟲及蟎類,而用於種子處理、莖葉散佈、土壤施用、水面施用等。
以下,揭示可藉由本發明之有害生物防除劑進行防除之各種農業害蟲及蟎類之具體例。
(1)鱗翅目(Lepidoptera)之蝶或蛾
(a)燈蛾科(Arctiidae)之蛾,例如美國白蛾(Hyphantria cunea)、暗點燈蛾(Lemyra imparilis);
(b)稜巢蛾科(Bucculatricidae)之蛾,例如梨稜巢蛾(Bucculatrix pyrivorella);
(c)蛀果蛾科(Carposinidae),例如桃蛀果蛾(Carposina sasakii);
(d)草螟科(Crambidae)之蛾,例如絹野螟屬(Diaphania spp.)之棉瓜絹野螟(Diaphania indica)、黃瓜絹野螟(Diaphania nitidalis);例如稈野螟屬(Ostrinia spp.)之亞洲玉米螟(Ostrinia furnacalis)、歐洲玉米螟(Ostrinia nubilalis)、紫玉米螟(Ostrinia scapulalis);其他之水稻二化螟(Chilo suppressalis)、稻縱捲葉螟(Cnaphalocrocis medinalis)、桃蛀螟(Conogethes punctiferalis)、巨座玉米螟(Diatraea grandiosella)、桑絹絲野螟(Glyphodes pyloalis)、菜心螟(Hellula undalis)、早熟禾擬莖草螟(Parapediasia teterrella);
(e)麥蛾科(Gelechiidae)之蛾,例如甘薯麥蛾(Helcystogramma triannulella)、棉紅鈴蟲(Pectinophora gossypiella)、馬鈴薯麥蛾(Phthorimaea operculella)、麥蛾(Sitotroga cerealella);
(f)尺蛾科(Geometridae)之蛾,例如大造橋蟲(Ascotis selenaria);
(g)細蛾科(Gracillariidae)之蛾,例如茶細蛾(Caloptilia theivora)、柑橘潛葉蛾(Phyllocnistis citrella)、金紋細蛾(Phyllonorycter ringoniella);
(h)弄蝶科(Hesperiidae)之蝶,例如稻弄蝶(Parnara guttata);
(i)枯葉蛾科(Lasiocampidae)之蛾,例如天幕毛蟲(Malacosoma neustria);
(j)毒蛾科(Lymantriidae)之蛾,例如毒蛾屬(Lymantria spp.)之舞毒蛾(Lymantria dispar)、松針毒蛾(Lymantria monacha);其他之茶毒蛾(Euproctis pseudoconspersa)、旋古毒蛾(Orgyia thyellina);
(k)潛蛾科(Lyonetiidae)之蛾,例如潛蛾屬(Lyonetia spp.)之桃潛葉蛾(Lyonetia clerkella)、銀紋潛葉蛾(Lyonetia prunifoliella malinella);
(l)夜蛾科(Noctuidae)之蛾,例如斜紋夜蛾屬(Spodoptera spp.)之淡劍襲夜蛾(Spodoptera depravata)、南方灰翅夜蛾(Spodoptera eridania)、甜菜夜蛾(Spodoptera exigua)、草地貪夜蛾(Spodoptera frugiperda)、非洲棉葉蟲蛾(Spodoptera littoralis)、斜紋夜蛾(Spodoptera litura);例如苜蓿銀紋夜蛾屬(Autographa spp.)之丫紋夜蛾(Autographa gamma)、黑點銀紋夜蛾(Autographa nigrisigna);例如地老虎屬(Agrotis spp.)之小地老虎(Agrotis ipsilon)、黃地老虎(Agrotis segetum);例如棉鈴蟲屬(Helicoverpa spp.)之棉鈴蟲(Helicoverpa armigera)、煙夜蛾(Helicoverpa assulta)、玉米穗蟲(Helicoverpa zea);例如實夜蛾屬(Heliothis spp.)之棉麥蛾(Heliothis armigera)、煙芽夜蛾(Heliothis virescens);其他之白斑煩夜蛾(Aedia leucomelas)、銀紋夜蛾(Ctenoplusia agnata)、枯豔葉夜蛾(Eudocima tyrannus)、甘藍夜蛾(Mamestra brassicae)、黏夜蛾(Mythimna separata)、稻螟蛉(Naranga aenescens)、日本小眼夜蛾(Panolis japonica)、疆夜蛾(Peridroma saucia)、大豆尺夜蛾(Pseudoplusia includens)、粉紋夜蛾(Trichoplusia ni);
(m)瘤蛾科(Nolidae)之蛾,例如埃及鑽夜蛾(Earias insulana);
(n)粉蝶科(Pieridae)之蝶,例如粉蝶屬(Pieris spp.)之大菜粉蝶(Pieris brassicae)、日本紋白蝶(Pieris rapae crucivora);
(o)菜蛾科(Plutellidae)之蛾,例如蔥菜蛾屬(Acrolepiopsis spp.)之蔥菜蛾(Acrolepiopsis sapporensis)、鈴木蔥菜蛾(Acrolepiopsis suzukiella);其他之小菜蛾(Plutella xylostella);
(p)螟蛾科(Pyralidae)之蛾,例如粉斑螟蛾(Cadra cautella)、南美玉米苗斑螟(Elasmopalpus lignosellus)、豆莢螟(Etiella zinckenella)、大蠟螟(Galleria mellonella);
(q)天蛾科(Sphingidae)之蛾,例如煙草天蛾屬(Manduca spp.)之番茄天蛾(Manduca quinquemaculata)、煙草天蛾(Manduca sexta);
(r)展足蛾科(Stathmopodidae)之蛾,例如柿展足蛾(Stathmopoda masinissa);
(s)蕈蛾科(Tineidae)之蛾,例如衣蛾(Tinea translucens);
(t)捲蛾科(Tortricidae)之蛾,例如褐帶捲蛾屬(Adoxophyes spp.)之茶小捲葉蛾(Adoxophyes honmai)、蘋果小捲葉蛾(Adoxophyes orana);例如黃捲蛾屬(Archips spp.)之梨黃捲蛾(Archips breviplicanus)、蘋果捲葉蛾(Archips fuscocupreanus);其他之雲杉捲葉蛾(Choristoneura fumiferana)、蘋果小捲蛾(Cydia pomonella)、女貞細捲蛾(Eupoecilia ambiguella)、梨小實心蟲(Grapholitha molesta)、後黃捲葉蛾(Homona magnanima)、大豆食心蟲(Leguminivora glycinivorella)、葡萄花翅小捲蛾(Lobesia botrana)、豆小捲葉蛾(Matsumuraeses phaseoli)、蘋褐捲蛾(Pandemis heparana)、葡萄長鬚捲葉蛾(Sparganothis pilleriana);
(u)巢蛾科(Yponomeutidae)之蛾,例如蛀果蛾(Argyresthia conjugella)。
(2)纓翅目(Thysanoptera)害蟲
(a)管薊馬科(Phlaeothripidae)之例如柿管薊馬(Ponticulothrips diospyrosi);
(b)纓翅科(Thripidae)之例如花薊馬屬(Frankliniella spp.)之臺灣花薊馬(Frankliniella intonsa)、西方花薊馬(Frankliniella occidentalis);例如薊馬屬(Thrips spp.)之棕櫚薊馬(Thrips palmi)、蔥薊馬(Thrips tabaci);其他溫室薊馬(Heliothrips haemorrhoidalis)、茶黃薊馬(Scirtothrips dorsalis)。
(3)半翅目(Hemiptera)之害蟲
(A)古喙亞目(Archaeorrhyncha)
(a)飛虱科(Delphacidae)之例如灰飛虱(Laodelphax striatella)、褐飛虱(Nilaparvata lugens)、甘蔗扁角飛虱(Perkinsiella saccharicida)、白背飛虱(Sogatella furcifera)。
(B)盾喙亞目(Clypeorrhyncha)
(a)葉蟬科(Cicadellidae)之例如小綠葉蟬屬(Empoasca spp.)之馬鈴薯小綠葉蟬(Empoasca fabae)、小綠葉蟬(Empoasca nipponica)、小貫小綠葉蟬(Empoasca onukii)、板井小綠葉蟬(Empoasca sakaii);其他之葡萄葉蟬(Arboridia apicalis)、黑胸二室葉蟬(Balclutha saltuella)、二點大葉蟬(Epiacanthus stramineus)、介體昆蟲葉蟬(Macrosteles striifrons)、黑尾葉蟬(Nephotettix cinctinceps)。
(C)半翅亞目(Heteroptera)
(a)蛛緣蝽科(Alydidae)之例如豆蜂緣蝽(Riptortus clavatus);
(b)緣蝽科(Coreidae)之例如稻棘緣蝽(Cletus punctiger)、中華稻緣蝽(Leptocorisa chinensis);
(c)長蝽科(Lygaeidae)之例如麥長蝽(Blissus leucopterus)、甘蔗長蝽(Cavelerius saccharivorus)、小翅瓢簞長亀蟲(Togo hemipterus);
(d)盲蝽科(Miridae)之例如Halticus insularis、美洲牧草盲蝽(Lygus lineolaris)、棉盲蝽(Psuedatomoscelis seriatus)、西伯利亞狹盲蝽(Stenodema sibiricum)、赤條纖盲蝽(Stenotus rubrovittatus)、赤鬚盲蝽(Trigonotylus caelestialium);
(e)蝽科(Pentatomidae)之例如稻綠蝽屬(Nezara spp.)之黑鬚稻綠蝽(Nezara antennata)、稻綠蝽(Nezara viridula);例如北二星蝽屬(Eysarcoris spp.)之北二星蝽(Eysarcoris aeneus)、日本二星蝽(Eysarcoris lewisi)、廣二星蝽(Eysarcoris ventralis)、其他之斑鬚蝽(Dolycoris baccarum)、皺紋菜蝽(Eurydema rugosum)、綠豔椿象(Glaucias subpunctatus)、茶翅蝽(Halyomorpha halys)、壁蝽(Piezodorus hybneri)、珀椿象(Plautia crossota)、稻黑蝽(Scotinophora lurida);
(f)紅蝽科(Pyrrhocoridae)之例如棉紅蝽(Dysdercus cingulatus);
(g)姬緣蝽科(Rhopalidae)之例如黃伊緣蝽(Rhopalus msculatus);
(h)盾背蝽科(Scutelleridae)之例如麥扁盾蝽(Eurygasterintegriceps);
(i)綱蝽科(Tingidae)之例如梨冠網蝽(Stephanitis nashi)。
(D)胸喙亞目(Sternorrhyncha)
(a)球蚜科(Adelgidae)之例如落葉松球蚜(Adelges laricis);
(b)粉虱科(Aleyrodidae)例如小粉虱屬(Bemisia spp.)之銀葉粉虱(Bemisia argentifolii)、煙粉虱(Bemisia tabaci);其他黑刺粉虱(Aleurocanthus spiniferus)、柑橘粉虱(Dialeurodes citri)、溫室粉虱(Trialeurodes vaporariorum);
(c)蚜科(Aphididae)例如蚜蟲屬(Aphis spp.)之豆蚜(Aphis craccivora)、蠶豆蚜(Aphis fabae)、草螟根蚜(Aphis forbesi)、棉蚜(Aphis gossypii)、蘋蚜(Aphis pomi)、接骨木蚜(Aphis sambuci)、捲葉蟲蚜(Aphis spiraecola);例如縊管蚜屬(Rhopalosiphum spp.)之玉米蚜(Rhopalosiphum maidis)、稻麥蚜(Rhopalosiphum padi);例如西圓尾蚜屬(Dysaphis spp.)之車前圓尾蚜(Dysaphis plantaginea)、羊蹄根瘤蚜(Dysaphis radicola);例如麥芽管蚜屬(Macrosiphum spp.)之麥長管蚜(Macrosiphum avenae)、馬鈴薯長管蚜(Macrosiphum euphorbiae);例如瘤蚜屬(Myzus spp.)之李瘤蚜(Myzus cerasi)、桃蚜(Myzus persicae)、黃藥子瘤蚜(Myzus varians);其他之豌豆長管蚜(Acyrthosiphon pisum)、茄溝無網蚜(Aulacorthum solani)、李短尾蚜(Brachycaudus helichrysi)、甘藍蚜(Brevicoryne brassicae)、草莓毛管蚜(Chaetosiphon fragaefolii)、大尾蟲蚜(Hyalopterus pruni)、刺菜超瘤蚜(Hyperomyzus lactucae)、菜縊管蚜(Lipaphis erysimi)、巢菜修尾蚜(Megoura viciae)、麥無網長管蚜(Metopolophium dirhodum)、萵苣蚜(Nasonovia ribis-nigri)、忽布疣蚜(Phorodon humuli)、麥二叉蚜(Schizaphis graminum)、麥長管蚜(Sitobion avenae)、桔二叉蚜(Toxoptera aurantii);
(d)介殼蟲科(Coccidae)之例如蠟蚧屬(Ceroplastes spp.)之角蠟蚧(Ceroplastes ceriferus)、紅蠟蚧(Ceroplastes rubens);
(e)盾蚧科(Diaspididae)之白盾蚧屬(Pseudaulacaspis spp.)之桑盾蚧(Pseudaulacaspis pentagona)、李白盾蚧(Pseudaulacaspis prunicola);例如尖盾蚧屬(Unaspis spp.)之康片盾蚧(Unaspis euonymi)、矢尖蚧(Unaspis yanonensis);其他之紅圓蚧(Aonidiella aurantii)、梨盾蚧(Comstockaspis perniciosa)、茶單盾蚧(Fiorinia theae)、牡丹網盾蚧(Pseudaonidia paeoniae);
(f)綿蚧科(Margarodidae)之例如草覆蚧(Drosicha corpulenta)、吹綿蚧(Icerya purchasi);
(g)根瘤蚜科(Phylloxeridae)之例如葡萄根瘤蚜(Viteus vitifolii);
(h)粉蚧科(Pseudococcidae)之例如臀紋粉蚧屬(Planococcus spp.)之柑橘粉蚧(Planococcus citri)、富士粉蚧(Planococcus kuraunhiae);其他之根粉蚧(Phenacoccus solani)、康氏粉蚧(Pseudococcus comstocki);
(i)木虱科(Psyllidae)之例如木虱屬(Psylla spp.)之蘋果木虱(Psylla mali)、梨木虱(Psylla pyrisuga);其他之柑橘木虱(Diaphorina citri)。
(4)多食亞目(Polyphaga)之害蟲
(a)竊蟲科(Anobiidae)之例如煙竊蟲(Lasioderma serricorne);
(b)捲葉象科(Attelabidae)之例如金綠捲象(Byctiscus betulae)、梨虎象(Rhynchites heros);
(c)長蟲科(Bostrichidae)之例如粉蟲(Lyctus brunneus);
(d)三錐象鼻蟲科(Brentidae)之例如甘薯蟻象(Cylas formicarius);
(e)吉丁蟲科(Buprestidae)之例如梨窄吉丁(Agrilus sinuatus);
(f)天牛科(Cerambycidae)之例如星天牛(Anoplophora malasiaca)、松褐天牛(Monochamus alternatus)、黃星桑天牛(Psacothea hilaris)、虎天牛(Xylotrechus pyrrhoderus);
(g)葉甲科(Chrysomelidae)之例如豆象屬(Bruchus spp.)之豌豆象(Bruchus pisorum)、蠶豆象(Bruchus rufimanus);例如玉米根蟲屬(Diabrotica spp.)之長角葉甲(Diabrotica barberi)、黃瓜甲蟲(Diabrotica undecimpunctata)、玉米根螢葉甲(Diabrotica virgifera);例如條跳甲屬(Phyllotreta spp.)之菁淡足跳甲(Phyllotreta nemorum)、黃條葉蚤(Phyllotreta striolata);其他之黃守瓜(Aulacophora femoralis)、綠豆象(Callosobruchus chinensis)、甜菜大龜甲(Cassida nebulosa)、甜菜跳甲(Chaetocnema concinna)、馬鈴薯葉甲(Leptinotarsa decemlineata)、水稻負泥蟲(Oulema oryzae)、茄窄胸跳甲(Psylliodes angusticollis);
(h)瓢蟲科(Coccinellidae)之例如食植瓢蟲屬(Epilachna spp.)之墨西哥豆瓢蟲(Epilachna varivestis)、酸醬瓢蟲(Epilachna vigintioctopunctata);
(i)象鼻蟲科(Curculionidae)之例如花象屬(Anthonomus spp.)之墨西哥棉鈴象(Anthonomus grandis)、梨花象(Anthonomus pomorum);例如象蟲屬(Sitophilus spp.)之穀象(Sitophilus granarius)、玉米象(Sitophilus zeamais);其他之稻象甲(Echinocnemus squameus)、西印度甘薯象甲(Euscepes postfasciatus)、松樹皮象(Hylobius abietis)、苜蓿葉象甲(Hypera postica)、稻水象甲(Lissohoptrus oryzophilus)、葡萄黑象甲(Otiorhynchus sulcatus)、豌豆根瘤象(Sitona lineatus)、尖隱喙象(Sphenophorus venatus);
(j)叩甲科(Elateridae)之例如紋叩甲屬(Melanotus spp.)之褐紋金針蟲(Melanotus fortnumi)、甘蔗櫛叩頭蟲(Melanotus tamsuyensis);
(k)露尾甲科(Nitidulidae)之例如突露尾甲(Epuraea domina);
(l)金龜子科(Scarabaeidae)之例如麗金龜屬(Anomala spp.)之大綠麗金龜(Anomala cuprea)、紅銅麗金龜(Anomala rufocuprea);其他之金花金龜(Cetonia aurata)、小綠花金龜(Gametis jucunda)、小栗鰓金龜(Heptophylla picea)、大栗鰓角金龜(Melolontha melolontha)、日本麗金龜(Popillia japonica);
(m)小蠹科(Scolytidae)之例如雲杉八齒小蠹(Ips typographus);
(n)隱翅蟲科(Staphylinidae)之例如毒隱翅蟲(Paederus fuscipes);
(o)擬步甲科(Tenebrionidae)之例如黃粉蟲(Tenebrio molitor)、赤擬穀盜(Tribolium castaneum);
(p)穀盜蟲科(Trogossitidae)之例如大穀盜(Tenebroides mauritanicus)。
(5)雙翅目(Diptera)之害蟲
(A)雙翅亞目(Brachycera)
(a)潛蠅科(Agromyzidae)之例如斑潛蠅屬(Liriomyza spp.)之瓜斑潛蠅(Liriomyza bryoniae)、蔥斑潛蠅(Liriomyza chinensis)、美洲斑潛蠅(Liriomyza sativae)、三葉斑潛蠅(Liriomyza trifolii);其他之豌豆彩潛蠅(Chromatomyia horticola)、日本稻潛蠅(Agromyza oryzae);
(b)花蠅科(Anthomyiidae)之例如地種蠅屬(Delia spp.)之灰地種蠅(Delia platura)、甘藍地種蠅(Delia radicum);其他之肖藜泉蠅(Pegomya cunicularia);
(c)果蠅科(Drosophilidae)之例如果蠅屬(Drosophila spp.)之黑腹果蠅(Drosophila melanogaster)、斑翅果蠅(Drosophila suzukii);
(d)水蠅科(Ephydridae)之例如稻潛葉蠅(Hydrellia griseola);
(e)莖蠅科(Psilidae)之例如蘿蔔莖蠅(Psila rosae);
(f)實蠅科(Tephritidae)之例如果實蠅屬(Bactrocera spp.)之瓜實蠅(Bactrocera cucurbitae)、桔小實蠅(Bactrocera dorsalis);例如繞實蠅屬(Rhagoletis spp.)之櫻桃繞實蠅(Rhagoletis cerasi)、蘋果繞實蠅(Rhagoletis pomonella);其他之地中海實蠅(Ceratitis capitata)、橄欖實蠅(Dacus oleae)。
(B)長角亞目(Nematocera)
(a)癭蚊科(Cecidomyiidae)之例如大豆癭蚊(Asphondylia yushimai)、高粱癭蚊(Contarinia sorghicola)、黑森癭蚊(Mayetiola destructor)、麥紅吸漿蟲(Sitodiplosis mosellana)。
(6)直翅目(Orthoptera)之害蟲
(a)蝗科(Acrididae)之例如沙漠蝗屬(Schistocerca spp.)之美國沙漠蝗(Schistocerca americana)、沙漠蝗(Schistocerca gregaria);其他之澳大利亞災蝗(Chortoicetes terminifera)、摩洛哥戟紋蝗(Dociostaurus maroccanus)、東亞飛蝗(Locusta migratoria)、褐蝗(Locustana pardalina)、紅翅蝗(Nomadacris septemfasciata)、小翅稻蝗(Oxya yezoensis);
(b)蟋蟀科(Gryllidae)之例如家蟋蟀(Acheta domestica)、黃臉油葫蘆(Teleogryllus emma);
(c)螻蛄科(Gryllotalpidae)之例如螻蛄(Gryllotalpa orientalis);
(d)蟲斯科(Tettigoniidae)之例如溫室灶馬(Tachycines asynamorus)。
(7)蟎類(Acari)
(A)無氣門目(Astigmata)之粉蟎亞目(Acaridida)
(a)粉蟎科(Acaridae)之蟎,例如根蟎屬(Rhizoglyphus spp.)之刺足根蟎(Rhizoglyphus echinopus)、羅賓根蟎(Rhizoglyphus robini);例如食酪蟎屬(Tyrophagus spp.)之溫室食酪蟎(Tyrophagus neiswanderi)、塵食酪蟎(Tyrophagus perniciosus)、腐食酪蟎(Tyrophagus putrescentiae)、似食酪蟎(Tyrophagus similis);其他之粗腳粉蟎(Acarus siro)、橢圓食粉蟎(Aleuroglyphus ovatus)、菌食嗜菌蟎(Mycetoglyphus fungivorus);
(B)前氣門目(Prostigmata)之蝠蟎亞目(Actinedida)
(a)葉蟎科(Tetranychidae)之蟎,例如苔蟎屬(Bryobia spp.)之苜蓿苔蟎(Bryobia praetiosa)、果苔蟎(Bryobia rubrioculus);例如始葉蟎屬(Eotetranychus spp.)之柑橘始葉蟎(Eotetranychus asiaticus)、北始葉蟎(Eotetranychus boreus)、樸始葉蟎(Eotetranychus celtis)、膝狀始葉蟎(Eotetranychus geniculatus)、柑橘始葉蟎(Eotetranychus kankitus)、李始葉蟎(Eotetranychus pruni)、木始葉蟎(Eotetranychus shii)、史氏始葉蟎(Eotetranychus smithi)、桑始葉蟎(Eotetranychus suginamensis)、彎鉤始葉蟎(Eotetranychus uncatus);例如小爪蟎屬(Oligonychus spp.)之本島小爪蟎(Oligonychus hondoensis)、咖啡小爪蟎(Oligonychus ilicis)、落葉松小爪蟎(Oligonychus karamatus)、芒果小爪蟎(Oligonychus mangiferus)、水杉小爪蟎(Oligonychus orthius)、鱷梨小爪蟎(Oligonychus perseae)、蝦夷松小爪蟎(Oligonychus pustulosus)、稻小爪蟎(Oligonychus shinkajii)、針葉小爪蟎(Oligonychus ununguis);例如全爪蟎屬(Panonychus spp.)之柑橘全爪蟎(Panonychus citri)、桑全爪蟎(Panonychus mori)、蘋果全爪蟎(Panonychus ulmi);例如葉蟎屬(Tetranychus spp.)之朱砂葉蟎(Tetranychus cinnabarinus)、神澤氏葉蟎(Tetranychus kanzawai)、盧氏葉蟎(Tetranychus ludeni)、山楂葉蟎(Tetranychus quercivorus)、豆葉蟎(Tetranychus phaselus)、二斑葉蟎(Tetranychus urticae)、斑翅葉蟎(Tetranychus viennensis)、伊凡氏葉蟎(Tetranychus evansi);例如缺爪蟎屬(Aponychus spp.)之竹缺爪蟎(Aponychus corpuzae)梧桐缺爪蟎(Aponychus firmianae);例如綠葉蟎屬(Sasanychus spp.)之綠葉蟎(Sasanychus akitanus)、姬綠葉蟎(Sasanychus pusillus);例如裂爪蟎屬(Shizotetranychus spp.)之嗜竹裂爪蟎(Shizotetranychus celarius)、長裂爪蟎(Shizotetranychus longus)、芒草裂爪蟎(Shizotetranychus miscanthi)、列氏裂爪蟎(Shizotetranychus recki)、原列爪蟎(Shizotetranychus schizopus);其他之酢醬草如葉蟎(Tetranychina harti)、孔雀杜克蟎(Tuckerella pavoniformis)、Yezonychus sapporensis;
(b)細鬚蟎科(Tenuipalpidae)之蟎,例如短鬚蟎屬(Brevipalpus spp.)之葡萄細鬚蟎(Brevipalpus lewisi)、卵形短鬚蟎(Brevipalpus obovatus)、紫紅短鬚蟎(Brevipalpus phoenicis)、仙人掌短鬚蟎(Brevipalpus russulus)、溫室細鬚蟎(Brevipalpus californicus);例如細鬚蟎屬(Tenuipalpus spp.)之太平洋細鬚蟎(Tenuipalpus pacificus)、柿細鬚蟎(Tenuipalpus zhizhilashviliae);其他之菠蘿長葉蟎(Dolichotetranychus floridanus);
(c)癭蟎科(Eriophyidae)之蟎,例如癭蟎屬(Aceria spp.)之柿癭蟎(Aceria diospyri)、榕癭蟎(Aceria ficus)、日本癭蟎(Aceria japonica)、枸杞癭蟎(Aceria kuko)、香石竹癭蟎(Aceria paradianthi)、Aceria tiyingi、鬱金香癭蟎(Aceria tulipae)、Aceria zoysiea;例如癭蟎屬(Eriophyes spp.)之千葉癭蟎(Eriophyes chibaensis)、梅鏽蟎(Eriophyes emarginatae);例如刺皮癭蟎屬(Aculops spp.)之番茄刺皮癭蟎(Aculops lycopersici)、皮氏刺皮癭蟎(Aculops pelekassi);例如真刺癭蟎屬(Aculus spp.)之福氏真刺癭蟎(Aculus fockeui)、斯氏真刺癭蟎(Aculus schlechtendali);其他之茶橙癭蟎(Acaphylla theavagrans)、茶葉癭蟎(Calacarus carinatus)、葡萄癭蟎(Colomerus vitis)、葡萄葉鏽蟎(Calepitrimerus vitis)、棗葉鏽蟎(Epitrimerus pyri)、金木植羽癭蟎(Paraphytoptus kikus)、羅漢松植羽癭蟎(Paracalacarus podocarpi)、柑橘鏽蟎(Phyllocotruta citri);
(d)線蟎科(Transonemidae)之蟎,例如跗線蟎屬(Tarsonemus spp.)之雙葉跗線蟎(Tarsonemus bilobatus)、細腳跗線蟎(Tarsonemus waitei);其他之櫻草植食蟎(Phytonemus pallidus)、茶跗線蟎(Polyphagotarsonemus latus);
(e)葉爪蟎科(Penthaleidae)之蟎,例如葉爪蟎屬(Penthaleus spp.)之紅頭葉爪蟎(Penthaleus erythrocephalus)、麥圓食蜱蟎(Penthaleus major)。
本發明之有害生物防除劑可與殺菌劑、殺蟲/殺蟎劑、殺線蟲劑、殺土壤害蟲劑等之其他有效成分、植物調節劑、協力劑、肥料、土壤改良劑、動物用飼料等混用或併用。
對於本發明之雜芳基唑化合物與其他有效成分之組合,可期待關於殺蟲、殺蟎、殺線蟲活性之協同效果。協同效果可依據慣例,根據Colby式(Colby.S.R.;Calculating Synergistic and Antagonistic Responses of Herbicide Combinations;Weeds 15,第20~22頁,1967)進行確認。
以下,揭示可與本發明之有害生物防除劑混用或併用之殺蟲/殺蟎劑、殺線蟲劑、殺土壤害蟲劑、驅蟲劑等之具體例。
(1)乙醯膽鹼酯酶抑制劑:
(a)胺甲酸酯系:棉靈威(alanycarb)、得滅克(aldicarb)、免敵克(bendiocarb)、免扶克(benfuracarb)、丁酮威(butocarboxim)、丁酮碸威(butoxycarboxim)、加保利(carbaryl)、加保扶(carbofuran)、丁基加保扶(carbosulfan)、愛芬克(ethiofencarb)、丁基滅必虱(fenobucarb)、覆滅蟎(formetanate)、呋線威(furathiocarb)、異丙威(isoprocarb)、滅賜克(methiocarb)、納乃得(methomyl)、歐殺滅(oxamyl)、比加普(pirimicarb)、安丹(propoxur)、硫敵克(thiodicarb)、久效威(thiofanox)、唑蚜威(triazamate)、混殺威(trimethacarb)、一氯代二甲苯(XMC,Xylene Monochloride)、滅爾虱(xylylcarb);芬硫克(fenothiocarb)、滅必虱(MIPC)、滅爾蝨(MPMC)、速滅威(MTMC,M Tolyl Methyl Carbamate)、碸滅威(aldoxycarb)、除害威(allyxycarb)、安美加(aminocarb)、必克虱(bufencarb)、除線威(cloethocarb)、斯美地(metam-sodium)、普滅克(promecarb);
(b)有機磷系:歐殺松(acephate)、亞滅松(azamethiphos)、乙基穀速松(azinphos ethyl)、甲基穀速松(azinphos methyl)、硫線磷(cadusafos)、氯氧磷(chlorethoxyfos)、克芬松(chlorfenvinphos)、氯甲磷(chlormephos)、陶斯松(chlorpyrifos)、甲基陶斯松、牛壁逃(coumaphos)、氰乃松(cyanophos)、滅賜松(demeton-S-methyl)、大利松(diazinon)、二氯松(dichlorvos)/磷酸2,2-二氯乙烯基二甲基酯(DDVP,Dimethyl Dichloro Vinyl Phosphate)、雙特松(dicrotophos)、大滅松(dimethoate)、甲基毒蟲畏(dimethylvinphos)、二硫松(disulfoton)、一品松(EPN,Ethyl P-Nitrophenyl)、愛殺松(ethion)、普伏松(ethoprophos)、胺磺磷(famphur)、芬滅松(fenamiphos)、撲滅松(fenitrothion)、芬殺松(fenthion)、福賽絕(fosthiazate)、飛達松(heptenophos)、菸鹼硫磷(imicyafos)、亞芬松(isofenphos)、水胺硫磷(isocarbophos)、加福松(isoxathio)、馬拉松(malathion)、滅加松(mecarbam)、達馬松(methamidophos)、滅大松(methidathion)、美文松(mevinphos)、亞素靈(monocrotophos)、乃力松(naled)、歐滅松(omethoate)、滅多松(oxydemeton-methyl)、巴拉松(parathion)、甲基巴拉松、賽達松(phenthoate)、福瑞松(phorate)、裕必松(phosalone)、益滅松(phosmet)、福賜米松(phosphamidon)、辛硫磷(phoxim)、亞特松(pirimiphos-methyl)、布飛松(profenofos)、撲達松(propetamphos)、普硫松(prothiofos)、白克松(pyraclofos)、必芬松(pyridaphenthion)、拜裕松(quinalphos)、硫特普(sulfotep)、嘧丙磷(tebupirimfos)、亞培松(temephos)、託福松(terbufos)、樂本松(tetrachlorvinphos)、硫滅松(thiometon)、三落松(triazophos)、三氯松(trichlorfon)、繁米松(vamidothion);乙基溴磷松(bromophos-ethyl)、二溴磷(BRP)、加芬松(carbophenothion)、施力松(cyanofenphos)、殺螟腈(CYAP)、滅賜松碸(demeton-S-methylsulfone)、得拉松(dialifos)、氯線磷(dichlofenthion)、殺力松(dioxabenzofos)、益多松(etrimfos)、繁福松(fensulfothion)、吡氟硫磷(flupyrazofos)、大福松(fonofos)、安果(formothion)、甲基異柳磷(phosmethylan)、依殺松(isazofos)、阿發松(iodofenphos)、滅克松(methacrifos)、乙基亞特松(pirimiphos-ethyl)、磷蟲威(phosphocarb)、丙蟲磷(propaphos)、飛克松(prothoate)、乙丙硫磷(sulprofos)。
(2)GABA(Gamma Aminobutyric Acid,γ-胺基丁酸)-功能性氯離子通道拮抗劑:乙醯蟲腈(acetoprole)、氯丹(chlordane)、安殺番(endosulfan)、乙蟲清(ethiprole)、芬普尼(fipronil)、氟蟲腈(pyrafluprole)、派瑞樂(pyriprole);毒殺芬(camphechlor)、飛布達(heptachlor)、得氯蟎(dienochlor)。
(3)鈉離子通道調節劑:阿納寧(acrinathrin)、右旋亞列寧(d-cis-trans allethrin)、右旋反式亞列寧、畢芬寧(bifenthrin)、百亞列寧(bioallethrin)、百亞列寧S-環戊基異構物、百列滅寧(bioresmethrin)、乙氰菊酯(cycloprothrin)、賽扶寧(cyfluthrin)、β-賽扶寧(beta-cyfluthrin)、賽洛寧(cyhalothrin)、λ-賽洛寧、γ-賽洛寧、賽滅寧(cypermethrin)、亞滅寧(alphacypermethrin)、β-賽滅寧、θ-賽滅寧、ζ-賽滅寧、賽酚寧(cyphenothrin)[(1R)-反式異構物]、第滅寧(deltamethrin)、益避寧(empenthrin)[(EZ)-(1R)-異構物]、益化利(esfenvalerate)、依芬寧(ethofenprox)、芬普寧(fenpropathrin)、芬化利(fenvalerate)、護賽寧(flucythrinate)、氟氯苯菊酯(flumethrin)、τ-福化利(taufluvalinate)、合芬寧(halfenprox)、依普寧(imiprothrin)、克特寧(kadethrin)、百滅寧(permethrin)、酚丁滅虱(phenothrin)[(1R)-反式異構物]、普亞列寧(prallethrin)、除蟲菊酯(pyrethrum)、列滅寧(resmethrin)、矽護芬(silafluofen)、七氟菊酯(tefluthrin)、治滅寧(tetramethrin)[(1R)-異構物]、泰滅寧(tralomethrin)、拜富寧(transfluthrin);亞列寧(allethrin)、除蟲菊精(pyrethrin)、除蟲菊精I、除蟲菊精II、丙氟菊酯(profluthrin)、四氟甲醚菊酯(dimefluthrin)、生物環呋菊酯(bioethanomethrin)、生物氯菊酯(biopermethrin)、反式百滅寧(trans-permethrin)、五氟苯菊酯(fenfluthrin)、吡氯氰菊酯(fenpirithrin)、溴氟菊酯(flubrocythrinate)、三氟醚菊酯(flufenprox)、美特寧(metofluthrin)、丙三苯醚菊酯(protrifenbute)、皮苄呋菊酯(pyresmethrin)、環戊烯丙菊酯(terallethrin)。
(4)菸鹼性乙醯膽鹼受體促效劑:亞滅培(acetamiprid)、可尼丁(clothianidin)、達特南(dinotefuran)、益達胺(imidacloprid)、烯啶蟲胺(nitenpyram)、硝蟲噻𠯤(nithiazine)、賽果培(thiacloprid)、賽滅速殺(thiamethoxam)、氟啶蟲胺腈(sulfoxaflor)、菸鹼、4-[(6-氯-3-吡啶基甲基)(2,2-二氟乙基)胺基]呋喃-2(5H)-酮(flupyradifurone)。
(5)菸鹼性乙醯膽鹼受體異位調節劑(allosteric modulator):賜諾特(spinetoram)、賜諾殺(spinosad)。
(6)氯化物通道活化劑:阿巴汀(abamectin)、因滅汀(emamectin 苯并ate)、林皮沒丁(lepimectin)、密滅汀(milbemectin);害獲滅(ivermectin)、色拉菌素(selamectin)、多拉菌素(doramectin)、依普菌素(eprinomectin)、莫西菌素(moxidectin)、殺蟎菌素(milbemycin)、殺蟎菌素肟(milbemycin oxime)、奈馬克丁(nemadectin)。
(7)保幼激素類似物:烯蟲乙酯(hydroprene)、烯蟲炔酯(kinoprene)、美賜平(methoprene)、芬諾克(fenoxycarb)、百利普芬(pyriproxyfen);苯蟲醚(diofenolan)、保幼醚(epofenonane)、烯蟲硫酯(triprene)。
(8)其他非特異性抑制劑:溴甲烷、氯化苦(chloropicrin)、磺醯氟(sulfuryl fluoride)、硼砂、吐酒石。
(9)同翅目選擇性拒食劑:氟尼尼胺(flonicamid)、派滅淨(pymetrozine)、新喹唑啉(pyrifluquinazon)。
(10)蟎類生育抑制劑:克芬蟎(clofentezine)、氟蟎𠯤(diflovidazin)、合賽多(hexythiazox)、依殺蟎(etoxazole)。
(11)微生物源昆蟲中腸內膜破壞劑:蘇力菌以色列亞種(Bacillus thuringiensis subsp. Israelensis)、球形桿菌(Bacillus sphaericus)、蘇力菌鯰澤亞種(Bacillus thuringiensis subsp. Aizawai)、蘇力菌庫斯克亞種(Bacillus thuringiensis subsp. Kurstaki)、蘇力菌擬步行亞種(Bacillus thuringiensis subsp. Tenebrionis)、Bt作物蛋白質:Cry1Ab、Cry1Ac、Cry1Fa、Cry1A.105、Cry2Ab、Vip3A、mCry3A、Cry3Ab、Cry3Bb、Cry34Ab1/Cry35Ab1。
(12)粒線體ATP生合成酵素抑制劑:汰芬諾克(diafenthiuron)、亞環錫(azocyclotin)、錫蟎丹(cyhexatin)、芬布錫(fenbutatin oxide)、歐蟎多(propargite)、得脫蟎(tetradifon)。
(13)氧化磷酸化解偶聯劑(uncoupling agent):克凡派(chlorfenapyr)、氟蟲胺(sulfluramid)、二硝甲酚(DNOC);百蟎克、大脫蟎(dinobuton)、白粉克。
(14)菸鹼性乙醯膽鹼受體通道阻斷劑:免速達(bensultap)、培丹鹽酸鹽(cartap hydrochloride);沙蠶毒素(nereistoxin);殺蟲單(thiosultap-monosodium)、硫賜安(thiocyclam)。
(15)甲殼素合成抑制劑:雙三氟蟲脲(bistrifluron)、克福隆(chlorfluazuron)、二福隆(diflubenzuron)、氟環脲(flucycloxuron)、氟芬隆(flufenoxuron)、六福隆(hexaflumuron)、祿芬隆(lufenuron)、諾伐隆(novaluron)、諾福隆(noviflumuron)、得福隆(teflubenzuron)、三福隆(triflumuron)、布芬淨(buprofezin)、氟佐隆(fluazuron)。
(16)雙翅目蛻皮干擾劑:賽滅淨(cyromazine)。
(17)蛻皮激素受體促效劑:可芬諾(chromafenozide)、合芬隆(halofenozide)、滅芬諾(methoxyfenozide)、得芬諾(tebufenozide)。
(18)章魚胺受體促效劑:三亞蟎(amitraz)、得米地曲(demiditraz)、殺蟲脒(chlordimeform)。
(19)粒線體電子傳遞系統複合體III抑制劑:亞醌蟎(acequinocyl)、嘧蟎酯(fluacrypyrim)、愛美松(hydramethylnon)。
(20)粒線體電子傳遞系統複合體I抑制劑:芬殺蟎(fenazaquin)、芬普蟎(fenpyroximate)、畢汰芬(pyrimidifen)、比達本(pyridaben)、得芬瑞(tebufenpyrad)、脫芬瑞(Tolfenpyrad)、魚藤酮(rotenone)。
(21)電位依賴性鈉離子通道阻斷劑:因得克(indoxacarb)、美氟綜(metaflumizone)。
(22)乙醯輔酶A羧化酶抑制劑:賜派芬(spirodiclofen)、螺甲蟎酯(spiromesifen)、賜派滅(spirotetramat)。
(23)粒線體電子傳遞系統複合體IV抑制劑:好達勝(Aluminium phosphide)、磷化鈣、磷化氫(phosphine)、磷化鋅、氰化物。
(24)粒線體電子傳遞系統複合體II抑制劑:唑蟎氰(cyenopyrafen)、丁氟蟎酯(cyflumetofen)、pyflubumide。
(25)利阿諾定(Ryanodine)受體調節劑:克安勃(chlorantraniliprole)、氰蟲醯胺(cyantraniliprole)、氟苯蟲醯胺(flubendiamide)、cyclaniliprole、tetraniliprole。
(26)混合功能氧化酶抑制劑化合物:協力精(piperonyl butoxide)。
(27)蛛毒素(latrophilin)受體作用藥:酯肽(depsipeptide)、環狀酯肽、24員環狀酯肽、艾莫德斯(emodepside)。
(28)其他藥劑(作用機制未知):印楝素(azadirachtin)、西脫蟎(benzoximate)、必芬蟎(bifenazate)、新殺蟎(bromopropylate)、滅蟎猛(chinomethionat)、冰晶石(cryolite)、大克蟎(dicofol)、啶蟲丙醚(pyridalyl);苯氯噻𠯤(benclothiaz)、硫、磺胺蟎酯(amidoflumet)、1,3-二氯丙烯、二氯異丙醚(DCIP,dichlorodiisopropylether)、溴蟎酯(phenisobromolate)、苯蟎特(苯并mate)、聚乙醛(metaldehyde)、克氯苯(chlorobenzilate)、氯噻唑(clothiazoben)、環蟲腈(dicyclanil)、fenoxacrim、氟硝二苯胺(fentrifanil)、氟苯滅(flubenzimin)、氟芬那辛(fluphenazine)、紅鈴蟲性誘素(gossyplure)、金龜子性誘素(japonilure)、㗁蟲酮(metoxadiazone)、石油、油酸鈉、殺蟎好(tetrasul)、苯蟎噻(triarathene);afidopyropen、flometoquin、丁烯氟蟲腈(flufiprole)、氟碸靈(fluensulfone)、氯氟醚菊酯(meperfluthrin)、四氟醚菊酯(tetramethylfluthrin)、溴代吡咯腈(tralopyril)、四氟甲醚菊酯(dimefluthrin)、甲基新癸醯胺(methylneodecanamide);fluralaner、afoxolaner、fluxametamide、5-[5-(3,5-二氯苯基)-5-三氟甲基-4,5-二氫異㗁唑-3-基]-2-(1H-1,2,4-三唑-1-基)苯甲腈(CAS:943137-49-3)、broflanilide、其他間位二醯胺類(meta-diamide)。
(29)驅蟲劑:
(a)苯并咪唑系:芬苯達唑(fenbendazole)、阿苯達唑(albendazole)、三氯苯達唑(triclabendazole)、奧苯達唑(oxibendazole)、甲苯達唑(mebendazole)、奧芬達唑(oxfendazole)、帕苯達唑(parbendazole)、氟苯達唑(flubendazole);苯硫胍(febantel)、奈托比胺(netobimin)、多保淨(thiophanate);腐絕(thiabendazole)、坎苯達唑(cambendazole);
(b)柳醯胺苯系:氯氰磺柳胺(closantel)、氯羥柳胺(oxyclozanide)、碘醚柳胺(rafoxanide)、氯硝柳胺(niclosamide);
(c)取代苯酚系:硝羥碘苄腈(nitroxynil)、硝異硫氰二苯醚(nitroscanate);
(d)嘧啶系:抗蟲靈(pyrantel)、摩朗得(morantel);
(e)咪唑并噻唑系:左旋咪唑(levamisole)、四咪唑(tetramisole);
(f)四氫嘧啶系:吡喹酮(praziquantel)、依西太爾(epsiprantel);
(g)其他驅蟲藥:環戊二烯類(cyclodiene)、雷雅尼雅(ryania)、氯舒隆(clorsulon)、甲硝噠唑(metronidazole)、得米地曲(demiditraz);
哌𠯤、乙胺𠯤(diethylcarbamazine)、雙氯酚(dichlorophen)、monepantel、tribenzymidine、阿米登太(amidantel);thiacetalsamide、merolsamine、硫乙胂胺酸(arsenamide)。
以下,揭示可與本發明之有害生物防除劑混用或併用之殺菌劑之具體例。
(1)核酸生合成抑制劑:
(a)RNA聚合酶I抑制劑:本達樂(benalaxyl)、右本達樂(benalaxyl-M);呋霜靈(furalaxyl);滅達樂(metalaxyl)、右滅達樂、歐殺斯(oxadixyl)、克拉康(clozylacon)、呋醯胺(ofurace);
(b)腺苷脫胺酶(adenosine deaminase)抑制劑:福拉比(bupirimate)、二甲嘧酚(dimethirimol)、乙嘧酚(ethirimol);
(c)DNA/RNA合成抑制劑:殺紋寧(hymexazol);辛噻酮(octhilinone);
(d)DNA拓樸異構酶II抑制劑:歐索林酸(oxolinic acid)。
(2)有絲核分裂抑制劑及細胞分裂抑制劑:
(a)β-微管蛋白聚合抑制劑:免賴得(benomyl)、貝芬替(carbendazim)、苯咪唑菌(chlorfenazole)、麥穗寧(fuberidazole)、涕必靈(thiabendazole);多保淨(thiophanate)、甲基多保淨(thiophanate-methyl);乙黴威(diethofencarb);座賽胺(zoxamide);噻唑菌胺(ethaboxam);
(b)細胞分裂抑制劑:賓克隆(pencycuron);
(c)類血影蛋白(spectrin)蛋白質之非定域化抑制劑:氟吡菌胺(fluopicolide)。
(3)呼吸抑制劑:
(a)複合體I NADH氧化還原酵素抑制劑:二氟林(diflumetorim);脫芬瑞(tolfenpyrad);
(b)複合體II琥珀酸脫氫酵素抑制劑:麥鏽靈(benodanil)、福多寧(flutolanil)、滅普寧(mepronil);艾索非他滅(isofetamid);氟吡菌醯胺(fluopyram);甲呋醯胺(fenfuram)、茂穀樂(furmecyclox);萎鏽靈(carboxin)、嘉保信(oxycarboxin);賽氟滅(thifluzamide);苯并烯氟菌唑(benzovindiflupyr)、必殺芬(bixafen)、氟唑菌醯胺(fluxapyroxad)、福拉比(furametpyr)、吡唑萘菌胺(isopyrazam)、噴福芬(penflufen)、吡噻菌胺(penthiopyrad)、氟唑環菌胺(sedaxane);白克列(boscalid);
(c)複合體III還原型輔酶(Ubiquinol)氧化酶Qo抑制劑:亞托敏(azoxystrobin)、丁香菌酯(coumoxystrobin)、甲香菌酯(coumethoxystrobin)、烯肟菌酯(enoxastrobin)、氟菌蟎酯(flufenoxystrobin)、啶氧菌酯(picoxystrobin)、唑菌酯(pyraoxystrobin);百克敏(pyraclostrobin)、唑胺菌酯(pyrametostrobin)、三環吡菌威(triclopyricarb);克收欣(kresoxim-methyl)、三氟敏(trifloxystrobin);醚菌胺(dimoxystrobin)、烯肟菌胺(fenaminstrobin)、苯氧菌胺(metominostrobin)、肟醚菌胺(orysastrobin);凡殺同(famoxadone);氟嘧菌酯(fluoxastrobin);咪唑菌酮(fenamidone);吡菌苯威(pyribencarb);
(d)複合體III還原型輔酶還原酵素Qi抑制劑:賽座滅(cyazofamid);安美速(amisulbrom);
(e)氧化性磷酸化解偶聯劑:百蟎克(binapacryl)、消蟎多(meptyldinocap)、白粉克(dinocap);扶吉胺(fluazinam);富米綜(ferimzone);
(f)氧化磷酸化抑制劑(ATP合成酵素之抑制劑):三苯醋錫、三苯氯錫、三苯羥錫;
(g)ATP生產抑制劑:硫矽菌胺(silthiofam);
(h)複合體III:細胞色素bcl(泛醌還原酵素)之Qx(未知)抑制劑:辛唑嘧菌胺(ametoctradin)。
(4)胺基酸及蛋白質合成抑制劑
(a)甲硫胺酸生合成抑制劑:胺撲滅(andoprim)、賽普洛(cyprodinil)、滅派林(mepanipyrim)、派美尼(pyrimethanil);
(b)蛋白質合成抑制劑:殺稻瘟菌素(blasticidin)-S;嘉賜黴素(kasugamycin)、鹽酸嘉賜黴素;鏈黴素(streptomycin);土黴素(oxytetracycline)。
(5)訊號傳遞抑制劑:
(a)訊號傳遞抑制劑:快諾芬(quinoxyfen)、丙氧喹啉(proquinazid);
(b)滲透壓訊號傳遞中之MAP/組胺酸激酶抑制劑:拌種咯(fenpiclonil)、護汰寧(fludioxonil)、克氯得(chlozolinate)、依普同(iprodione)、撲滅寧(procymidone)、免克寧(vinclozolin)。
(6)脂質及細胞膜合成抑制劑:
(a)磷脂質生合成、甲基轉移酶抑制劑:護粒松(edifenphos)、丙基喜樂松(iprobenfos)、白粉松(pyrazophos);亞賜圃(isoprothiolane);
(b)脂質之過氧化劑:聯苯、地茂散(chloroneb)、大克爛(dicloran)、五氯硝基苯(quintozene)、四氯硝基苯(tecnazene)、脫克松(tolclofos-methyl);依得利(etridiazole);
(c)作用於細胞膜之藥劑:碘代丙炔基丁基甲胺酸酯(iodocarb)、霜黴威(propamocarb)、鹽酸霜黴威、乙膦酸霜黴威(propamocarb fosetylate)、胺丙威(prothiocarb);
(d)干擾病原菌細胞膜之微生物:枯草桿菌、枯草桿菌QST713株、枯草桿菌FZB24株、枯草桿菌MBI600株、枯草桿菌D747株;
(e)干擾細胞膜之藥劑:互生葉白千層(melaleuca alternifolia)(茶樹)之萃取物。
(7)細胞膜之固醇生合成抑制劑:
(a)固醇生合成中之C14位之去甲基化抑制劑:賽福寧(triforine);比芬諾(pyrifenox)、啶菌㗁唑(pyrisoxazole);芬瑞莫(fenarimol)、呋嘧醇(Flurprimidol)、尼瑞莫(nuarimol);依滅列(imazalil)、硫酸依滅列、㗁咪唑(oxpoconazole)、稻瘟酯(pefurazoate)、撲克拉(prochloraz)、賽福座(triflumizole)、烯霜苄唑(viniconazole);
阿紮康唑(azaconazole)、比多農(bitertanol)、溴克座(bromuconazole)、環克座(cyproconazole)、苄氯三唑醇(diclobutrazole)、待克利(difenoconazole)、達克利(diniconazole)、右達克利、依普座(epoxiconazole)、乙環唑(etaconazole)、芬克座(fenbuconazole)、氟喹唑(fluquinconazole)、護矽得(flusilazole)、護汰芬(flutriafol)、呋菌唑(fluconazole)、順式呋菌唑、菲克利(hexaconazole)、易胺座(imibenconazole)、種菌唑(ipconazole)、滅特座(metconazole)、邁克尼(myclobutanil)、平克座(penconazole)、普克利(propiconazole)、氟喹唑(fluquinconazole)、矽氟唑(simeconazole)、得克利(tebuconazole)、四克利(tetraconazole)、三泰芬(triadimefon)、三泰隆(triadimenol)、滅菌唑(triticonazole);丙硫菌唑(prothioconazole)、伏立康唑(voriconazole);
(b)固醇生合成中之Δ14還原酵素及Δ8→Δ7-異構酶之抑制劑:
十二嗎啉(aldimorph)、嗎菌靈(dodemorph)、嗎菌靈乙酸鹽、芬普福(fenpropimorph)、三得芬(tridemorph);苯鏽啶(fenpropidin)、粉病靈(piperalin);葚孢菌素(spiroxamine);
(c)固醇生合成系之C4位去甲基化中之3-酮還原酵素抑制劑:環醯菌胺(fenhexamid);胺苯吡菌酮(fenpyrazamine);
(d)固醇生合成系之角鯊烯環氧酶抑制劑:稗草畏(pyributicarb);萘替芬(naftifine)、特比萘芬(terbinafine)。
(8)細胞壁合成抑制
(a)海藻糖酶(trehalase)抑制劑:維利黴素(validamycin);
(b)甲殼素合成酵素抑制劑:多氧菌素(polyoxin)、保粒黴素丁(polyoxorim);
(c)纖維素合成酵素抑制劑:達滅芬(dimethomorph)、氟嗎啉(flumorph)、丁吡嗎啉(pyrimorph);苯噻菌胺(benthiavalicarb)、纈黴威(iprovalicarb)、托普洛卡(tolprocarb)、維利芬那(valifenalate);曼普胺(mandipropamid)。
(9)黑色素生合成抑制劑
(a)黑色素生合成之還原酵素抑制劑:四氯苯酞(fthalide);百快隆(pyroquilon);三賽唑(tricyclazole);
(b)黑色素生合成之脫水酵素抑制劑:加普胺(carpropamid);二氯西莫(diclocymet);芬諾尼(fenoxanil)。
(10)宿主植物之抗性誘導劑:
(a)作用於水楊酸合成路徑之藥劑:酸化苯并噻二唑-S-甲酯。
(b)其他:撲殺熱(probenazole);噻醯菌胺(tiadinil);異噻菌胺(isotianil);昆布醣(laminarin);大虎杖(giant knotweed)萃取液。
(11)作用性不明之藥劑:克絕(cymoxanil)、三乙膦酸鋁(fosetyl-aluminium)、磷酸(磷酸鹽)、克枯爛(tecloftalam)、咪唑𠯤(triazoxide)、氟硫滅(flusulfamide)、達滅淨(diclomezine)、滅速克(methasulfocarb)、環氟菌胺(cyflufenamid)、滅芬農(metrafenone)、哌瑞芬酮(pyriofenone)、多果定(dozine)、多果定自由鹼、氟替尼(flutianil)。
(12)具有多作用點之劑:銅(銅鹽)、波爾多液、氫氧化銅、萘二甲酸銅、氧化銅、氧氯化銅、硫酸銅、硫、硫製品、多硫化鈣;福美鐵(ferbam)、代森鋅錳(mancozeb)、錳乃浦(maneb)、銅錳乃浦(mancopper)、免得爛(metiram)、代森福美鋅(polycarbamate)、甲基鋅乃浦(propineb)、得恩地(thiram)、鋅乃浦(zineb)、福美鋅(ziram);蓋普丹(captan)、四氯丹(captafol)、福爾培(folpet);四氯異苯(chlorothalonil);益發靈(dichlofluanid)、託福寧(tolylfluanid);克熱淨(guazatine)、克熱淨乙酸鹽(iminoctadine triacetate)、克熱淨烷苯磺酸鹽(iminoctadine trialbesilate);敵菌靈(anilazine);腈硫醌(dithianon);甲基克殺蟎(chinomethionate);氟美地(fluoroimide)。
(13)其他藥劑: DBEDC、氟佛配特(fluorfolpet)、雙胍乙酸鹽、雙(8-羥基喹啉)銅(II)、普羅帕脒(propamidine)、氯化苦(chloropicrin)、酯菌胺(cyprofuram)、農桿菌(agrobacterium)、3-苯并[b]噻吩-2-基-5,6-二氫-1,4,2-噻𠯤4-氧化物(bethoxazine)、二苯胺、異硫氰酸甲酯(MITC)、滅粉黴素(mildiomycin)、辣椒鹼(capsaicin)、硫雜靈(cufraneb)、噻普磺醯胺(cyprosulfamide)、邁隆(dazomet)、咪菌威(debacarb)、二氯酚(dichlorophen)、野燕枯(difenzoquat)、野燕枯甲基磺酸鹽、氟美醯胺(flumetover)、三乙膦酸鈣(fosetyl calcium)、三乙膦酸鈉(fosetyl natrium)、人間黴素(irumamycin)、遊黴素(natamycin)、異丙消(nitrothal isopropyl)、惡莫克(oxamocarb)、丙醇菌素鈉(propanosine sodium)、硝吡咯菌素(pyrrolnitrin)、喹啉類殺真菌劑(tebufloquin)、甲磺菌胺(tolnifanide)、氰菌胺(zarilamide)、Algophase、拌種靈(Amicarthiazol)、奧賽普林(Oxathiapiprolin)、代森聯鋅(metiram zinc)、苯噻唑(benthiazol)、水楊菌胺(trichlamide)、烯效唑(uniconazole)、滅粉黴素(mildiomycin)、氧代奮欣(Oxyfenthiin)、皮卡布西(picarbutrazox)。
以下,揭示可與本發明之有害生物防除劑混用或併用之植物調節劑之具體例。
脫落酸、激動素、苄基胺基嘌呤、1,3-二苯基脲、福芬素(forchlorfenuron)、噻苯隆(thidiazuron)、chlorfenuron、二氫玉米素、吉貝素A、吉貝素A4、吉貝素A7、吉貝素A3、1-甲基環丙烷、N-乙醯基胺基乙氧基乙烯基甘胺酸(別名:四烯雌酮、aviglycine)、胺氧基乙酸、硝酸銀、氯化鈷、IAA、4-CPA、果美生長素(cloprop)、2,4-D、MCPB、吲哚-3-丁酸、2,4-滴丙酸(dichlorprop)、酚硫殺(phenothiol)、1-萘基乙醯胺、吲熟酯(ethychlozate)、座果酸(cloxyfonac)、順丁烯二醯肼、2,3,5-三碘苯甲酸、水楊酸、水楊酸甲酯、(-)-茉莉酸(jasmonic acid)、茉莉酸甲酯、(+)-獨腳金醇(strigol)、(+)-脫氧獨腳金醇、(+)-列當醇(orobanchol)、(+)-高粱內酯(sorgolactone)、4-側氧基-4-(2-苯基乙基)胺基丁酸;益收生長素(ethephon)、克美素(chlormequat)、縮節胺(mepiquat chloride)、苄基腺嘌呤、5-胺乙醯丙酸。
[外部寄生蟲防除劑]
本發明之外部寄生蟲防除劑含有選自本發明之雜芳基唑化合物中之至少一種作為有效成分。關於本發明之外部寄生蟲防除劑所含之雜芳基唑化合物之量,只要顯示出外部寄生蟲之防除效果,則並無特別限制。
作為成為本發明之外部寄生蟲防除劑之處理對象的宿主動物,可列舉:人類、家畜哺乳動物(例如牛、馬、豬、綿羊、山羊等)、實驗動物(例如小鼠、大鼠、長爪沙鼠等)、寵物動物(例如倉鼠、豚鼠、狗、貓、馬、松鼠、兔、白鼬等)、野生及動物園之哺乳動物(猴、狐狸、鹿、野牛等)、家禽(火雞、鴨、雞、鵪鶉、蛾蝶等)、寵物鳥(鴿、鸚鵡、鷯哥、文鳥、小鸚鵡、白腰文鳥、金絲雀等)等恆溫動物;或鮭魚、鱒魚、錦鯉等魚類。此外,亦可列舉:蜜蜂、鍬形蟲、獨角仙。
本發明之外部寄生蟲防除劑可藉由公知之獸醫學方法(局部、經口、非經口或皮下投予)施用。作為該方法,可列舉:藉由錠劑、膠囊、飼料混入等對動物進行經口投予之方法;藉由浸漬液、栓劑、注射(肌內、皮下、靜脈內、腹腔內等)等對動物進行投予之方法;藉由噴霧、澆潑劑(pour-on)、滴劑(spot-on)等將油性或水性液劑進行局部投予之方法;將外部寄生蟲防除劑混入樹脂中,將上述混練物成形為項圈、耳環等適當形狀,並將該等佩戴於動物身體上而進行局部投予之方法等。
外部寄生蟲係寄生於宿主動物、尤其是恆溫動物之中及上。詳細而言,外部寄生蟲係寄生於宿主動物之背部、腋下、下腹部、腿內側部等並自動物獲取血液或膚皮等營養源以生息。作為外部寄生蟲,可列舉:蟎類、蝨子類、跳蚤類、蚊、刺繩、麻蠅等。以下,揭示可藉由本發明之外部寄生蟲防除劑進行防除之外部寄生蟲之具體例。
(1)蟎類(Acari)
皮刺蟎科(Dermanyssidae)之蟎、巨刺蟎科(Macronyssidae)之蟎、厲蟎科(Laelapidae)之蟎、瓦蟎科(Varroidae)之蟎、軟蜱科(Argasidae)之蟎、硬蜱科(Ixodidae)之蟎、癢蟎科(Psoroptidae)之蟎、疥蟎科(Sarcoptidae)之蟎、鳥腳蟎科(Knemidokoptidae)之蟎、蠕形蟎科(Demodixidae)之蟎、毛壁蝨科(Trombiculidae)之蟎、Coleopterophagus類等昆蟲寄生性之蟎。
(2)虱目(Phthiraptera)
血虱科(Haematopinidae)之虱、顎虱科(Linognathidae)之虱、短角鳥虱科(Menoponidae)之羽虱、長角鳥虱科(Philopteridae)之羽虱、獸羽虱科(Trichodectidae)之羽虱。
(3)蚤目(Siphonaptera)
蚤科(Pulicidae)之跳蚤,例如櫛首蚤屬(Ctenocephalides spp.)之跳蚤、犬櫛首蚤(Ctenocephalides canis)、貓櫛首蚤(Ctenocephalides felis);
潛蚤科(Tungidae)之跳蚤、角葉蚤科(Ceratophyllidae)之跳蚤、細蚤科(Leptopsyllidae)之跳蚤。
(4)半翅目(Hemiptera)。
(5)雙翅目(Diptera)之害蟲
蚊科(Culicidae)之蚊、蚋科(Simuliidae)之蚋、蠓科(Ceratopogonidae)之蠓、虻科(Tabanidae)之虻、家蠅科(Muscidae)之蠅、舌蠅科(Glossinidae)之舌蠅、麻蠅科之麻蠅、虱蠅科(Hippoboscidae)之蠅、麗蠅科(Calliphoridae)之蠅、狂蠅科(Oestridae)之蠅。
[內部寄生蟲防除或驅除劑]
本發明之內部寄生蟲防除或驅除劑含有選自本發明之雜芳基唑化合物中之至少一種作為有效成分。關於本發明之內部寄生蟲防除或驅除劑所含之雜芳基唑化合物之量,只要顯示出內部寄生蟲之防除效果,則並無特別限制。
成為本發明之內部寄生蟲防除劑或驅除劑之對象的寄生蟲係寄生於宿主動物尤其是恆溫動物或魚類之中(內部寄生蟲)。作為本發明之寄生蟲防除或驅除劑有效之宿主動物,可列舉:人類、家畜哺乳動物(例如牛、馬、豬、綿羊、山羊等)、實驗動物(例如小鼠、大鼠、長爪沙鼠等)、寵物動物(例如倉鼠、豚鼠、狗、貓、馬、松鼠、兔、白鼬等)、野生及動物園之哺乳動物(猴、狐狸、鹿、野牛等)、家禽(火雞、鴨、雞、鵪鶉、蛾蝶等)、寵物鳥(鴿、鸚鵡、鷯哥、文鳥、小鸚鵡、白腰文鳥、金絲雀等)等恆溫動物;或鮭魚、鱒魚、錦鯉等魚類。藉由防除及驅除寄生蟲,可預防或治療寄生蟲媒介之寄生蟲疾病。
作為防除或驅除對象之寄生蟲,可列舉以下者。
(1)膨結蟲目(Dioctophymatida)之線蟲類
(a)膨結蟲科(Dioctophymatidae)之膨結蟲,例如腎蟲屬(Dioctophyma spp.)之膨結蟲(Dioctophyma renale);
(b)紫貂胃蟲科(Soboliphymatidae)之膨結蟲,例如紫貂胃蟲屬(Soboliphyme spp.)之Soboliphyme abei、Soboliphyme baturini。
(2)毛首目(Trichocephalida)之線蟲類
(a)旋毛蟲科(Trichinellidae)之旋毛蟲,例如旋毛蟲屬(Trichinella spp.)之旋毛蟲(Trichinella spiralis);
(b)鞭蟲科(Trichuridae)之鞭蟲,例如即毛細線蟲屬(Capillaria spp.)之有環毛細線蟲(Capillaria annulata)、鳥食道毛細線蟲(Capillaria contorta)、肝毛細線蟲(Capillaria hepatica)、穿通毛細線蟲(Capillaria perforans)、狐膀胱毛細線蟲(Capillaria plica)、豬毛細線蟲(Capillaria suis);鞭蟲屬(Trichuris spp.)之犬鞭蟲(Trichuris vulpis)、牛鞭蟲(Trichuris discolor)、羊鞭蟲(Trichuris ovis)、斯氏鞭蟲(Trichuris skrjabini)、豬鞭蟲(Trichuris suis)。
(3)小桿線蟲目(Rhabditida)之線蟲類
類圓線蟲科(Strongyloididae)之類圓線蟲,例如類圓線蟲屬(Strongyloides spp.)之乳頭類圓線蟲(Strongyloides papillosus)、貓糞類圓線蟲(Strongyloides planiceps)、豬蘭氏類圓線蟲(Strongyloides ransomi)、豬糞類圓線蟲(Strongyloides suis)、糞類圓線蟲(Strongyloides stercoralis)、腫脹類圓線蟲(Strongyloides tumefaciens)、鼠糞類圓線蟲(Strongyloides ratti)。
(4)圓線蟲目(Strongylida)之線蟲類
鉤蟲科(Ancylostomatidae)之鉤蟲,例如鉤口線蟲屬(Ancylostoma spp.)之貓鉤口線蟲(Ancylostoma braziliense)、犬鉤口線蟲(Ancylostoma caninum)、十二指腸鉤口線蟲(Ancylostoma duodenale)、管形鉤口線蟲(Ancylostoma tubaeforme);彎口線蟲屬(Uncinaria stenocephala)之狹首彎口線蟲(Uncinaria stenocephala);仰口線蟲屬(Bunostomum spp.)之牛仰口線蟲(Bunostomum phlebotomum)、羊仰口線蟲(Bunostomum trigonocephalum)。
(5)圓線蟲目(Strongylida)之線蟲類
(a)管圓線蟲科(Angiostrongylidae)之線蟲,例如貓圓線蟲屬(Aelurostrongylus spp.)之貓肺蟲(Aelurostrongylus abstrusus);管圓線蟲屬(Angiostrongylus spp.)之血管圓線蟲(Angiostrongylus vasorum)、廣州管圓線蟲(Angiostrongylus cantonesis);
(b)環體線蟲科(Crenosomatidae)之線蟲,例如環體線蟲屬(Crenosoma spp.)之肺環體線蟲(Crenosoma aerophila)、狐環體線蟲(Crenosoma vulpis);
(c)似絲蟲科(Filaroididae)之線蟲,例如似絲蟲屬(Filaroides spp.)之肺似絲蟲(Filaroides hirthi)、歐氏似絲蟲(Filaroides osleri);
(d)後圓線蟲科(Metastrongylidae)之後圓線蟲,例如後圓線蟲屬(Metastrongylus spp.)之豬後圓線蟲(Metastrongylus apri)、Metastrongylus asymmetricus、複陰後圓形線蟲(Metastrongylus pudendotectus)、薩姆氏後圓線蟲(Metastrongylus salmi);
(e)比翼線蟲科(Syngamidae)之比翼線蟲,例如杯口線蟲屬(Cyathostoma spp.)之水鳥杯口線蟲(Cyathostoma bronchialis);比翼線蟲屬(Syngamus spp.)之斯氏比翼線蟲(Syngamus skrjabinomorpha)、氣管比翼線蟲(Syngamus trachea)。
(6)圓線蟲目(Strongylida)之線蟲類
(a)縱溝紐蟲科(Molineidae)之線蟲,例如細頸線蟲屬(Nematodirus spp.)之尖刺細頸線蟲(Nematodirus filicollis)、鈍刺細頸線蟲(Nematodirus spathiger);
(b)網尾線蟲科(Dictyocaulidae)之線蟲,例如網尾線蟲屬(Dictyocaulus spp.)之絲狀網尾線蟲(Dictyocaulus filaria)、胎生網尾線蟲(Dictyocaulus viviparus);
(c)撚轉胃蟲科(Haemonchidae)之線蟲,例如撚轉胃蟲屬(Haemonchus spp.)之撚轉血矛線蟲(Haemonchus contortus);長刺線蟲屬(Mecistocirrus spp.)之指形長刺線蟲(Mecistocirrus digitatus);
(d)撚轉胃蟲科(Haemonchidae)之線蟲,例如奧氏線蟲屬(Ostertagia spp.)之奧氏線蟲(Ostertagia ostertagi);
(e)似繞線蟲科(Heligmonellidae)之線蟲,例如日圓線蟲屬(Nippostrongylus spp.)之巴西日圓線蟲(Nippostrongylus braziliensis);
(f)毛圓線蟲科(Trichostrongylidae)之線蟲,例如毛圓線蟲屬(Trichostrongylus spp.)之艾氏毛圓線蟲(Trichostrongylus axei)、蛇形毛圓線蟲(Trichostrongylus colubriformis)、微細毛圓線蟲(Trichostrongylus tenuis);豬圓線蟲屬(Hyostrongylus spp.)之淡紅豬圓線蟲(Hyostrongylus rubidus);尖柱線蟲屬(Obeliscoides spp.)之穴兔尖柱線蟲(Obeliscoides cuniculi)。
(7)圓線蟲目(Strongylida)之線蟲類
(a)夏柏特線蟲科(Chabertiidae)之線蟲,例如夏柏特線蟲屬(Chabertia spp.)之綿羊夏柏特線蟲(Chabertia ovina);結節線蟲屬(Oesophagostomum spp.)之豬結節線蟲(Oesophagostomum brevicaudatum)、哥倫比亞結節線蟲(Oesophagostomum columbianum)、豬腸結節蟲(Oesophagostomum dentatum)、喬奇亞結節線蟲(Oesophagostomum georgianum)、結節線蟲(Oesophagostomum maplestonei)、長尾結節線蟲(Oesophagostomum quadrispinulatum)、牛結節線蟲(Oesophagostomum radiatum)、山羊結節線蟲(Oesophagostomum venulosum)、野豬結節線蟲(Oesophagostomum watanabei);
(b)腎線蟲科(Stephanuridae)之線蟲,例如腎線蟲屬(Stephanurus spp.)之有齒腎線蟲(Stephanurus dentatus);
(c)圓線蟲科(Strongylidae)之線蟲,例如圓線蟲屬(Strongylus spp.)之驢圓線蟲(Strongylus asini)、無齒圓線蟲(Strongylus edentatus)、馬圓線蟲(Strongylus equinus)、普通圓線蟲(Strongylus vulgaris)。
(8)蟯蟲目(Oxyurida)之線蟲類
蟯蟲科(Oxyuridae)之線蟲,例如蟯蟲屬(Enterobius spp.)之黑猩猩蟯蟲(Enterobius anthropopitheci)、蠕形住腸線蟲(Enterobius vermicularis);尖尾線蟲屬(Oxyuris spp.)之馬尖尾線蟲(Oxyuris equi);栓尾線蟲屬(Passalurus spp.)之安比瓜栓尾線蟲(Passalurus ambiguus)。
(9)蛔蟲目(Ascaridida)之線蟲類
(a)禽蛔蟲科(Ascaridiidae)之線蟲,例如禽蛔蟲屬(Ascaridia spp.)之雞蛔蟲(Ascaridia galli);
(b)異刺線蟲科(Heterakidae)之線蟲,例如異刺線蟲屬(Heterakis spp.)之貝拉異刺線蟲(Heterakis beramporia)、短刺異刺線蟲(Heterakis brevispiculum)、雞異刺線蟲(Heterakis gallinarum)、羊異刺線蟲(Heterakis pusilla)、雞異刺線蟲(Heterakis putaustralis);
(c)異尖線蟲科(Anisakidae)之線蟲,例如異尖線蟲屬(Anisakis spp.)之簡單異尖線蟲(Anisakis simplex);
(d)蛔蟲科(Ascarididae)之線蟲,例如蛔蟲屬(Ascaris spp.)之人類蛔蟲(Ascaris lumbricoides)、豬蛔蟲(Ascaris suum);副蛔蟲屬(Parascaris spp.)之馬副蛔蟲(Parascaris equorum);
(e)弓首線蟲科(Toxocaridae)之線蟲,例如弓首線蟲屬(Toxocara spp.)之犬弓首線蟲(Toxocara canis)、獅弓首線蟲(Toxocara leonina)、豬弓首線蟲(Toxocarasuum)、牛弓首線蟲(Toxocara vitulorum)、貓弓首線蟲(Toxocara cati)。
(10)旋尾線蟲目(Spirurida)之線蟲類
(a)盤尾絲蟲科(Onchocercidae)之線蟲,例如布魯絲蟲屬(Brugia spp.)之馬來布魯絲蟲(Brugia malayi)、彭亨布魯絲蟲(Brugia pahangi)、派特布魯絲蟲(Brugia patei);棘唇絲蟲屬(Dipetalonema spp.)之隱形棘唇絲蟲(Dipetalonema reconditum);惡絲蟲屬(Dirofilaria spp.)之犬惡絲蟲(Dirofilaria immitis);絲蟲屬(Filaria spp.)之羅阿絲蟲(Filaria oculi);盤尾絲蟲屬(Onchocerca spp.)之頸盤尾絲蟲(Onchocerca cervicalis)、牛盤尾絲蟲(Onchocerca gibsoni)、喉瘤盤尾絲蟲(Onchocerca gutturosa);
(b)絲狀線蟲科(Setariidae)之線蟲,例如絲狀線蟲屬(Setaria spp.)之指狀絲狀線蟲(Setaria digitata)馬絲狀線蟲(Setaria equina)、牛唇乳絲狀線蟲(Setaria labiatopapillosa)、馬氏絲狀線蟲(Setaria marshalli);吳策線蟲屬(Wuchereria spp.)之班氏吳策線蟲(Wuchereria bancrofti);
(c)絲狀線蟲科(Filariidae)之線蟲,例如副絲蟲屬(Parafilaria spp.)之多乳頭絲狀線蟲(Parafilaria multipapillosa);冠絲蟲屬(Stephanofilaria spp.)之艾氏冠絲蟲(Stephanofilaria assamensis)、德氏冠絲蟲(Stephanofilaria dedoesi)、Stephanofilaria kaeli、沖繩冠絲蟲(Stephanofilaria okinawaensis)、斯氏冠絲蟲(Stephanofilaria stilesi)。
(11)旋尾線蟲目(Spirurida)之線蟲類
(a)顎口線蟲科(Gnathostomatidae)之線蟲,例如顎口線蟲屬(Gnathostoma spp.)之陶氏顎口線蟲(Gnathostoma doloresi)、棘顎口線蟲(Gnathostoma spinigerum);
(b)柔線蟲科(Habronematidae)之線蟲,例如柔線蟲屬(Habronema spp.)之小口胃線蟲(Habronema majus)、小口胃線蟲(Habronema microstoma)、蠅胃線蟲(Habronema muscae);德拉希線蟲屬(Draschia spp.)之大口德拉希線蟲(Draschia megastoma);
(c)泡翼線蟲科(Physalopteridae)之線蟲,例如泡翼線蟲屬(Physaloptera spp.)之犬泡翼線蟲(Physaloptera canis)、狐泡翼線蟲(Physaloptera cesticillata)、Physaloptera erdocyona、獅泡翼線蟲(Physaloptera felidis)、成雙泡翼線蟲(Physaloptera gemina)、Physaloptera papilloradiata、貓泡翼線蟲(Physaloptera praeputialis)、Physaloptera pseudopraerutialis、稀泡翼線蟲(Physaloptera rara)、西伯利亞線蟲(Physaloptera sibirica)、Physaloptera vulpineus;
(d)筒線蟲科(Gongylonematidae)之線蟲,例如筒線蟲屬(Gongylonema spp.)之美麗筒線蟲(Gongylonema pulchrum);
(e)尾旋線蟲科(Spirocercidae)之線蟲,例如旋翼線蟲屬(Ascarops spp.)之圓形旋翼線蟲(Ascarops strongylina);
(f)吸吮線蟲科(Thelaziidae)之線蟲,例如吸吮線蟲屬(Thelazia spp.)之結膜吸吮線蟲(Thelazia callipaeda)、大口結膜吸吮線蟲(Thelazia gulosa)、淚管吸吮線蟲(Thelazia lacrymalis)、露德西吸吮線蟲(Thelazia rhodesi)、斯克里亞賓吸吮線蟲(Thelazia skrjabini)。
[針對其他有害生物之防除劑]
此外,本發明之雜芳基唑化合物於帶有毒針或毒液且對人獸施害之害蟲、作為各種病原體、病原菌之媒介之害蟲、對人造成不快感之害蟲(有毒害蟲、衛生害蟲、不快害蟲等)之防除效果方面亦優異。
以下,揭示其具體例。
(1)膜翅目(Hymenoptera)之害蟲
叉角葉蜂科(Argidae)之蜂、癭蜂科(Cynipidae)之蜂、松葉蜂科(Diprionidae)之蜂、蟻科(Formicidae)之蟻、蟻蜂科(Mutillidae)之蜂、胡蜂科(Vespidae)之蜂。
(2)其他害蟲
蜚蠊類(Blattodea)、白蟻類(termite)、蜘蛛類(Araneae)、蜈蚣類(Cetipede)、千足蟲類(millipede)、甲殼類(Crustacea)、溫帶臭蟲(Cimex lectularius)。
[種子處理劑或營養繁殖器官處理劑]
本發明之種子處理劑或營養繁殖器官處理劑含有選自本發明之雜芳基唑化合物中之至少一種作為有效成分。關於本發明之種子處理劑或營養繁殖器官處理劑所含之雜芳基唑化合物之量,只要顯示出防除效果,則並無特別限制。
所謂營養繁殖器官,意指植物之根、莖、葉等中之將該部位自本體切離後設置於土壤中之情形時具有生長能力者。作為營養繁殖器官,例如可列舉:塊根(tuberous root)、匍匐根(creeping root)、鱗莖(bulb)、球莖(corm或solid bulb)、塊莖(tuber)、根莖(rhizome)、匍匐枝(stolon)、擔根體(rhizophore)、莖段(cane cuttings)、繁殖體(propagule)及藤段(vine cutting)。再者,匍匐枝有時亦稱作走莖(runner),繁殖體亦稱作珠芽,分為肉芽(broad bud)及鱗芽(bulbil)。所謂藤段,意指甘薯或山藥等之苗條(葉及莖之統稱,shoot)。亦將鱗莖、球莖、塊莖、根莖、莖段、擔根體或塊根統稱作球根。薯類之栽培係藉由將塊莖種植於土壤中而開始,所使用之塊莖一般稱作種芋。
本發明之種子處理劑或營養繁殖器官處理劑係指以選自本發明之雜芳基唑化合物中之至少一種作為有效成分,混合適宜之固體載體或液體載體,視需要添加界面活性劑或其他製劑用輔助劑,製成水合劑、顆粒水合劑、懸浮劑或粉劑等形態之劑。本組合物通常與黏合劑混合使用。又,本組合物亦可含有黏合劑。作為含有黏合劑之本組合物,可列舉種子處理專用之懸浮劑(FS:Flowable concentrate for seed treatment)。
作為上述黏合劑,使用對植物種子或營養繁殖器官無植物毒性影響之接著性物質。具體而言,可使用選自由聚乙酸乙烯酯、聚乙烯醇、包含乙基纖維素、甲基纖維素、羥甲基纖維素、羥丙基纖維素及羧甲基纖維素之纖維素、聚乙烯吡咯啶酮、澱粉、改性澱粉、糊精、麥芽糊精、海藻酸鹽及包含聚葡萄胺糖之多糖類、明膠及包含玉米蛋白之蛋白質、阿拉伯膠、蟲膠、木質素磺酸鈣、以及甲基丙烯醯胺單體所組成之群中之至少1種。
藉由對種芋實施選自本發明之雜芳基唑化合物中之至少一種之處理,可有效率地防除有害生物。作為對種芋實施雜芳基唑化合物之處理之方法,可列舉:浸漬處理、粉衣處理或包衣處理等。又,於使用拖拉機種植種芋時,亦可藉由在拖拉機上噴灑含有雜芳基唑化合物之藥液而對種芋進行處理。
[水稻育苗箱處理用農藥粒狀組合物]
本發明之水稻育苗箱處理用農藥粒狀組合物(以下稱為「農藥粒狀組合物」)含有選自本發明之雜芳基唑化合物中之至少一種作為有效成分。關於本發明之農藥粒狀組合物所含之雜芳基唑化合物之量,只要顯示出防除效果,則並無特別限制。
農藥粒狀組合物可藉由各種方法獲得,例如藉由將調配有1種以上之有效成分與視需要之界面活性劑、黏合劑及無機載體等之粉狀組合物利用濕式造粒法進行擠出造粒等而獲得。更具體而言,將調整為特定粒度之有效成分與必要之界面活性劑、黏合劑及無機載體均勻地混合後,添加適量水進行混練,經由細孔篩網擠出成型,加以乾燥而製成農藥粒狀組合物。此時使用之細孔之大小通常較佳為0.5 mm~1.5 mm。
藉由如上方式獲得之農藥粒狀組合物之粒徑並無特別限制,平均粒徑較佳為0.5 mm~1.5 mm,尤佳為0.7 mm~1.5 mm。此種粒徑之造粒粒狀物可藉由造粒、乾燥後篩分而獲得。
視需要於農藥粒狀組合物中調配界面活性劑、黏合劑及無機載體。其中,作為界面活性劑,例如可列舉:聚乙二醇高級脂肪酸酯、聚氧乙烯烷基醚、聚氧乙烯烷基芳基醚、聚氧乙烯芳基苯基醚、山梨醇酐單烷化物等非離子性界面活性劑;烷基芳基磺酸鹽、二烷基磺酸鹽、烷基硫酸酯鹽、烷基磷酸酯鹽、烷基芳基硫酸酯鹽、烷基芳基磷酸酯鹽、聚氧乙烯烷基醚硫酸酯鹽、萘磺酸鹽及其縮合物、木質素磺酸鹽、丙烯酸與伊康酸之共聚物或甲基丙烯酸與伊康酸之共聚物、順丁烯二酸與苯乙烯之共聚物、順丁烯二酸與二異丁烯之共聚物及該等之鹼金屬鹽等多羧酸型高分子活性劑;聚氧乙烯芳基苯基醚磷酸酯鹽;聚氧乙烯芳基苯基醚硫酸酯鹽等陰離子性界面活性劑等。該界面活性劑之調配量通常為0.1重量份~5重量份,並無特別限定。
作為農藥粒狀組合物中調配之黏合劑,例如可列舉:羧甲基纖維素金屬鹽、聚乙烯醇、α化澱粉、糊精、三仙膠、瓜爾豆膠(guar seed gum)、蔗糖、聚乙烯吡咯啶酮、聚丙烯酸金屬鹽等,調配量通常為0.1重量份~5重量份,並無特別限定。進而,作為上述農藥粒狀組合物中調配之無機載體,並無特別限定,例如可列舉:黏土類、碳酸鈣、滑石、矽藻土、沸石、厄帖浦石、石膏、陶石等。
[土壤處理劑]
本發明中之所謂土壤處理,例如於欲實施保護免受有害生物之攝食等侵害之植物之根圈施用有效成分,藉此直接防除有害生物,或使有效成分自根部等滲透轉移至植物體內部而防除有害生物之方法,具體而言,例如可列舉:植穴處理(植穴散佈、植穴處理土壤混合)、植株根部處理(植株根部散佈、植株根部土壤混合、植株根部灌注、育苗後半期植株根部處理)、植溝處理(植溝散佈、植溝土壤混合)、作條處理(作條散佈、作條土壤混合、生育期作條散佈)、播種時作條處理(播種時作條散佈、播種時作條土壤混合)、全面處理(全面土壤散佈、全面土壤混合)、側條處理、水面處理(全面水面施用、邊緣水面施用)、其他土壤散佈處理(生育期粒劑葉面散佈、樹冠下或主幹周邊散佈、土壤表面散佈、土壤表面混合、播穴散佈、畦部地表面散佈、株間散佈)、其他灌注處理(土壤灌注、育苗期灌注、藥液注入處理、地際部灌注、藥液滴灌、化學灌溉)、育苗箱處理(育苗箱散佈、育苗箱灌注、育苗箱藥液湛水)、苗床處理(苗床散佈、苗床灌注、水秧田苗床散佈)、苗浸漬、育苗培土混合處理(床土混合、覆土混合)、播種時覆土前散佈、播種時覆土後散佈、莖注入處理、樹幹注入處理、樹幹散佈處理、其他處理(鋤入、表土混合、雨水滴落部混合、栽植地處理、粒劑花萼散佈、糊狀肥料混合)。
所謂水耕液處理,例如對水耕液等施用有效成分以使有效成分自欲實施保護免受有害生物攝食等侵害之植物之根部等滲透轉移至植物體內部,藉此保護該植物免受有害生物侵害之方法,具體而言,例如可列舉:水耕液混合、水耕液混入等。
又,亦可藉由將利用浸漬、含浸、塗佈、混入等方法使片狀或繩狀、帶狀、網狀之樹脂、紙、布等載體包含本發明組合物而成之製劑纏繞於植物上、於植物附近拉網、鋪於植株根部土壤上、覆於植物之栽培域等方法施用。
[餌劑]
本發明之餌劑含有選自本發明之雜芳基唑化合物中之至少一種作為有效成分。關於本發明之餌劑所含之雜芳基唑化合物之量,只要顯示出防除效果,則並無特別限制。
本發明之餌劑亦可視需要含有糖、碳水化合物、乳成分等攝取性提高成分、協力劑、防誤食劑、保存劑、香料、誘引劑等。本發明之餌劑通常可藉由將雜芳基唑化合物及水、視需要之上述其他成分加以混合而製備。於製備本發明之餌劑時,雜芳基唑化合物可為雜芳基唑化合物其本身,亦可為粉劑、水合劑、微膠囊劑、懸浮劑等製劑形態。
作為可藉由本發明之餌劑而有效地防除之有害生物,可列舉:輪紋蜚蠊、茶翅蜚蠊、黑蜚蠊等蜚蠊,Melanotus okinawensis等叩甲,日本小蟻、日本山蟻等蟻,煙草甲、藥材甲等竊蟲,赤擬榖盜、扁擬榖盜等擬榖盜,鋸扁蟲、角胸扁蟲等扁蟲,家白蟻、大和白蟻等白蟻,家蠅、黃腹廄蠅、蚤蠅、蝶蠅等蠅,赤家蚊、白線斑蚊、羽斑蚊、揺蚊等蚊。
作為本發明之餌劑之施用形態,可為本發明之餌劑本身形態,亦可為例如含浸於不織布、海綿、脫脂棉等中之狀態。將本水性餌劑或含浸有本餌劑之不織布、海綿、脫脂棉等置於例如杯、盤、瓶等容器內供驅除害蟲。此時,若製成包覆裝有本發明之餌劑之容器之外側,具有可供害蟲停留以攝取本發明之餌劑之一定程度之空間的裝置,則一般而言攝取性提高,有效果。
[植物生長促進劑]
本發明之植物生長促進劑含有選自本發明之雜芳基唑化合物中之至少一種作為有效成分。關於本發明之植物生長促進劑所含之雜芳基唑化合物之量,只要顯示出植物生長促進效果,則並無特別限制。
本發明之植物生長促進劑可視需要適當調配其他成分或載體等。
本發明之雜芳基唑化合物亦可單獨地作為植物生長促進劑而使用,但通常可與以雜芳基唑化合物作為有效成分之製劑中所慣用之固體載體、液體載體、分散劑、稀釋劑、乳化劑、展布劑及增黏劑等輔助劑進行混合,製成水合劑、液劑、油劑、粉劑、粒劑或溶膠劑(懸浮)等劑型而使用。
作為固體載體或液體載體,例如可列舉:滑石、黏土、膨潤土、高嶺土、矽藻土、蒙脫石、雲母、蛭石、石膏、碳酸鈣、白碳、木粉、澱粉、氧化鋁、矽酸鹽、糖聚合物、蠟類、水、醇類(甲醇、乙醇、正丙醇、異丙醇、正丁醇、乙二醇、苄醇等)、石油餾分(石油醚、煤油、溶劑石腦油等)、脂肪族或脂環式烴類(正己烷、環己烷等)、芳香族烴類(苯、甲苯、二甲苯、乙基苯、氯苯、異丙苯、甲基萘等)、鹵化烴類(氯仿、二氯甲烷等)、醚類(異丙醚、環氧乙烷、四氫呋喃等)、酮類(丙酮、甲基乙基酮、環己酮、甲基異丁基酮等)、酯類(乙酸乙酯、乙酸丁酯、乙二醇乙酸酯、乙酸戊酯等)、酸醯胺類(二甲基甲醯胺、二甲基乙醯苯胺等)、腈類(乙腈、丙腈、丙烯腈等)、亞碸類(二甲基亞碸等)、醇醚類(乙二醇單甲醚、乙二醇單乙醚等)等。
作為輔助劑,例如可列舉:非離子型界面活性劑(聚氧乙烯烷基醚、聚氧乙烯烷基酯、聚氧乙烯烷基苯基醚、聚氧乙烯山梨醇酐烷基酯、山梨醇酐烷基酯等)、陰離子型界面活性劑(烷基苯磺酸酯、烷基磺基丁二酸酯、聚氧乙烯烷基硫酸酯、芳基磺酸酯等)、陽離子型界面活性劑(烷基胺類、聚氧乙烯烷基胺類、四級銨鹽類等)、兩性型界面活性劑(烷基胺基乙基甘胺酸、烷基二甲基甜菜鹼等)、聚乙烯醇、羥丙基纖維素、羧甲基纖維素、阿拉伯膠、黃耆膠、三仙膠、聚乙酸乙烯酯、明膠、酪蛋白、海藻酸鈉等。
作為其他成分,可列舉:上述殺菌劑、殺蟲/殺蟎劑、殺線蟲劑、殺土壤害蟲劑等其他有效成分;植物調節劑、協力劑、肥料、土壤改良劑、動物用飼料等。
本發明之雜芳基唑化合物於植物生長促進劑中之含量根據製劑形態、施用方法、其他條件而各有不同,較佳為0.5~95質量%,尤佳為2~70質量%之範圍。
作為成為適用對象之植物,並無特別限定,例如可列舉:稻、大麥、小麥、稗、玉米、穀子等禾本科之穀物類;南瓜、蕪菁、甘藍、蘿蔔、白菜、菠菜、甜椒、蕃茄等蔬菜類;菊花、非洲菊、三色堇、蘭花、芍藥、鬱金香等花卉類;紅豆、菜豆、大豆、花生、蠶豆、豌豆等豆類;馬鈴薯、甘薯、芋頭、山芋、黑芋等薯類;蔥、洋蔥、藠頭等蔥類等。
作為本發明之植物生長促進劑之施用方法,可對植物施用(莖葉散佈)、可對植物之生長土壤施用(土壤施用)、可對田面水施用(水面施用)、可對種子施用(種子處理)等。
本發明之植物生長促進劑之施用量根據適用植物等而異,於莖葉散佈之情形時,較佳為每10公畝施用以有效成分濃度計1~10000 ppm之範圍、較佳為10~1000 ppm之溶液50~300 L,於土壤施用及水面施用之情形時,較佳為每10公畝以有效成分量計施用0.1~1000 g、尤佳為10~100 g。又,於種子處理之情形時,較佳為對1 Kg種子施用0.001~50 g之有效成分。
[製劑配方]
揭示若干本發明之有害生物防除劑、殺蟲或殺蟎劑、外部寄生蟲防除劑或者內部寄生蟲防除或驅除劑之製劑配方,但添加物及添加比率不應限定於該等實施例,可於較廣範圍內進行變化。製劑配方中之份表示重量份。
以下揭示農園藝用及水稻用之製劑配方。
(製劑1:水合劑)
將本發明之雜芳基唑化合物40份、矽藻土53份、高級醇硫酸酯4份、及烷基萘磺酸鹽3份均勻地混合並微細地粉碎,而獲得有效成分40%之水合劑。
(製劑2:乳劑)
將本發明之雜芳基唑化合物30份、二甲苯33份、二甲基甲醯胺30份、及聚氧乙烯烷基烯丙基醚7份進行混合溶解,而獲得有效成分30%之乳劑。
(製劑3:粒劑)
將本發明之雜芳基唑化合物5份、滑石40份、黏土38份、膨潤土10份、及烷基硫酸鈉7份均勻地混合並微細地粉碎後,造粒成直徑0.5~1.0 mm之粒狀,而獲得有效成分5%之粒劑。
(製劑4:粒劑)
將本發明之雜芳基唑化合物5份、黏土73份、膨潤土20份、磺琥珀酸二辛酯鈉鹽1份、及磷酸鉀1份充分地粉碎混合,添加水並將該等充分捏合後,進行造粒乾燥,而獲得有效成分5%之粒劑。
(製劑5:懸浮劑)
將本發明之雜芳基唑化合物10份、聚氧乙烯烷基烯丙基醚4份、聚羧酸鈉鹽2份、甘油10份、三仙膠0.2份、及水73.8份加以混合,進行濕式粉碎直至粒度成為3微米以下,而獲得有效成分10%之懸浮劑。
以下揭示外部寄生蟲防除劑、或者內部寄生蟲防除或驅除劑之製劑配方。
(製劑6:顆粒劑)
使本發明之雜芳基唑化合物5份溶解於有機溶劑中而獲得溶液,將上述溶液霧狀噴出至高嶺土94份及白碳1份之上,繼而使溶劑於減壓下蒸發。此種顆粒可與動物之餌食混合。
(製劑7:注入劑)
將本發明之雜芳基唑化合物0.1~1份與花生油99〜99.9份均勻地混合,繼而藉由殺菌過濾器進行過濾殺菌。
(製劑8:澆潑(pour−on)劑)
將本發明之雜芳基唑化合物5份、肉豆蔻酸酯10份、及異丙醇85份均勻地混合,而獲得澆潑劑。
(製劑9:滴(spot on)劑)
將本發明之雜芳基唑化合物10~15份、棕櫚酸酯10份、及異丙醇75~80份均勻地混合,而獲得滴劑。
(製劑10:噴霧劑)
將本發明之雜芳基唑化合物1份、丙二醇10份、及異丙醇89份均勻地混合,而獲得噴霧劑。
其次,揭示化合物之實施例而更具體地說明本發明。但本發明並不受以下之化合物實施例之任何限制。
[實施例1]
2-(5-(乙基磺醯基)-6-(1-甲基-5-(全氟丙基)-1H-咪唑-2-基)吡啶-3-基)嘧啶[2-(5-(ethylsulfonyl)-6-(1-methyl-5-(perfluoropropyl)-1H-imidazol-2-yl)pyridin-3-yl)pyrimidine]之合成(化合物編號b-19)之合成
(步驟1)2-溴-5-氯-3-(乙基硫基)吡啶[2-bromo-5-chloro-3-(ethylthio)pyridine]之合成
[化41]
使3-胺基-2-溴-5-氯吡啶(40.0 g)、及二乙基二硫醚(16.5 g)溶解於1,2-二氯乙烷(770 ml),將所獲得之溶液於室溫下攪拌。於其中添加亞硝酸第三丁酯(29.8 g),於50℃下加熱一晩。將所獲得之液體注入至水中,利用氯仿進行萃取。將所獲得之有機層利用飽和鹽水洗淨,經無水硫酸鎂乾燥並進行過濾。對濾液進行減壓濃縮。藉由矽膠管柱層析法對所獲得之濃縮物進行精製而獲得目標物30.0 g(產率62%)。
所獲得之目標物之1
H-NMR如下所示。1
H-NMR (CDCl3
) δ: 8.08 (1H, d), 7.37 (1H, d), 2.96 (2H, q), 1.42 (3H, t).
(步驟2)5-氯-3-(乙基硫基)-2-(1-甲基-1H-咪唑-2-基)吡啶[5-chloro-3-(ethylthio)-2-(1-methyl-1H-imidazol-2-yl)pyridine]之合成
[化42]
於反應容器中使1-甲基-1H-咪唑(4.0 g)溶解於四氫呋喃(200 ml),對反應容器進行氮氣置換。其後,冷卻至-70℃。於其中滴加2.65M正丁基鋰正己烷溶液(21 ml),於-70℃下攪拌30分鐘。於其中添加1M氯化鋅四氫呋喃溶液(83 ml),升溫至室溫,攪拌1小時。其後,添加2-溴-5-氯-3-(乙基硫基)吡啶(10.4 g)、及四(三苯基膦)鈀(2.4 g),對反應容器進行氮氣置換。其後,於加熱回流下攪拌一晩。將所獲得之液體注入至羅謝耳鹽水溶液中,利用乙酸乙酯進行萃取。將所獲得之有機層利用氫氧化鈉水溶液及飽和鹽水洗淨,經無水硫酸鎂乾燥並進行過濾。對濾液進行減壓濃縮。藉由矽膠管柱層析法對所獲得之濃縮物進行精製而獲得目標物9.65 g(產率92%)。
所獲得之目標物之1
H-NMR如下所示。1
H-NMR (CDCl3
) δ: 8.31 (1H, d), 7.59 (1H, d), 7.21 (1H, d), 6.99 (1H, d), 3.85 (3H, s), 2.92 (2H, q), 1.37 (3H, t).
(步驟3)5-氯-3-(乙基磺醯基)-2-(1-甲基-1H-咪唑-2-基)吡啶[5-chloro-3-(ethylsulfonyl)-2-(1-methyl-1H-imidazol-2-yl)pyridine]之合成
[化43]
使5-氯-3-(乙基硫基)-2-(1-甲基-1H-咪唑-2-基)吡啶(0.80 g)溶解於二氯甲烷(20 ml),冷卻至0℃。於其中添加70%間氯過苯甲酸(1.71 g),於室溫下攪拌5小時。將所獲得之液體注入至飽和碳酸氫鈉水溶液與飽和硫代硫酸鈉水溶液之混合溶液中,利用二氯甲烷進行萃取。將所獲得之有機層利用飽和鹽水洗淨,經無水硫酸鎂乾燥並進行過濾。對濾液進行減壓濃縮。藉由矽膠管柱層析法對所獲得之濃縮物進行精製而獲得目標物0.84 g(產率93%)。
所獲得之目標物之1
H-NMR如下所示。1
H-NMR (CDCl3
) δ: 8.83 (1H, d), 8.46 (1H, d), 7.14 (1H, d), 7.05 (1H, d), 3.93 (2H, q), 3.68 (3H, s), 1.34 (3H, t).
(步驟4)2-(5-溴-1-甲基-1H-咪唑-2-基)-5-氯-3-(乙基磺醯基)吡啶[2-(5-bromo-1-methyl-1H-imidazol-2-yl)-5-chloro-3-(ethylsulfonyl)pyridine]之合成
[化44]
使5-氯-3-(乙基磺醯基)-2-(1-甲基-1H-咪唑-2-基)吡啶(0.84 g)溶解於二氯甲烷(30 ml),冷卻至0℃。於其中添加N-溴丁二醯亞胺(0.50 g),於室溫下攪拌3小時。將所獲得之液體注入至水中,利用二氯甲烷進行萃取。將所獲得之有機層利用飽和鹽水洗淨,經無水硫酸鎂乾燥並進行過濾。對濾液進行減壓濃縮,藉由矽膠管柱層析法對所獲得之濃縮物進行精製而獲得目標物0.93 g(產率89%)。
所獲得之目標物之1
H-NMR如下所示。1
H-NMR (CDCl3
) δ: 8.83 (1H, d), 8.46 (1H, d), 7.13 (1H, s), 3.88 (2H, q), 3.62 (3H, s), 1.35 (3H, t).
(步驟5)5-氯-3-(乙基磺醯基)-2-(5-碘-1-甲基-1H-咪唑-2-基)吡啶[5-chloro-3-(ethylsulfonyl)-2-(5-iodo-1-methyl-1H-imidazol-2-yl)pyridine]之合成
[化45]
於反應容器中使2-(5-溴-1-甲基-1H-咪唑-2-基)-5-氯-3-(乙基磺醯基)吡啶(0.93 g)溶解於二㗁烷(26 ml),對反應容器進行氬氣置換。其後,於室溫下攪拌。於其中添加碘化鈉(1.92 g)、碘化銅(0.1 g)、及反式-N,N'-二甲基環己烷-1,2-二胺(0.15 g),於加熱回流下攪拌一晩。將所獲得之液體注入至水中,利用二氯甲烷進行萃取。將所獲得之有機層利用飽和鹽水洗淨,經無水硫酸鎂乾燥並進行過濾。對濾液進行減壓濃縮,藉由矽膠管柱層析法對所獲得之濃縮物進行精製而獲得目標物0.93 g(產率89%)。
所獲得之目標物之1
H-NMR如下所示。1
H-NMR (CDCl3
) δ: 8.84 (1H, d), 8.46 (1H, d), 7.23 (1H, s), 3.87 (2H, q), 3.62 (3H, s), 1.34 (3H, t).
(步驟6)5-氯-3-(乙基磺醯基)-2-(1-甲基-5-(全氟丙基)-1H-咪唑-2-基)吡啶[5-chloro-3-(ethylsulfonyl)-2-(1-methyl-5-(perfluoropropyl)-1H-imidazol-2-yl)pyridine]之合成
[化46]
於反應容器中使5-氯-3-(乙基磺醯基)-2-(5-碘-1-甲基-1H-咪唑-2-基)吡啶(0.68 g)溶解於N,N'-二甲基伸丙基脲(3 ml),對反應容器進行氬氣置換。其後,於室溫下攪拌。於其中添加碘化銅(0.57 g)、及雙(正全氟丙基)鋅-DMPU錯合物(1.96 g),於120℃下攪拌一晩。將所獲得之液體注入至飽和羅謝耳鹽水溶液中,利用乙酸乙酯進行萃取。將所獲得之有機層利用水及飽和鹽水洗淨,經無水硫酸鎂乾燥並進行過濾。對濾液進行減壓濃縮,藉由矽膠管柱層析法對所獲得之濃縮物進行精製而獲得目標物0.61 g(產率82%)。
所獲得之目標物之1
H-NMR如下所示。1
H-NMR (CDCl3
) δ: 8.89 (1H, d), 8.47 (1H, d), 7.50 (1H, s), 3.73 (2H, q), 3.65 (3H, s), 1.34 (3H, t).
(步驟7)2-(5-(乙基磺醯基)-6-(1-甲基-5-(全氟丙基)-1H-咪唑-2-基)吡啶-3-基)嘧啶[2-(5-(ethylsulfonyl)-6-(1-methyl-5-(perfluoropropyl)-1H-imidazol-2-yl)pyridin-3-yl)pyrimidine]之合成
[化47]
於反應容器中使5-氯-3-(乙基磺醯基)-2-(1-甲基-5-(全氟丙基)-1H-咪唑-2-基)吡啶(0.29 g)溶解於二㗁烷(10 ml),對反應容器進行氮氣置換。其後,於室溫下攪拌。於其中添加2-(三丁基錫烷基)嘧啶(0.35 g)、乙酸鈀(II)(0.03 g)、18%三環己基膦甲苯溶液(0.36 g)、及氟化銫(0.22 g),於加熱回流下攪拌一晩。將所獲得之液體注入至10%氟化鉀水溶液中,利用乙酸乙酯進行萃取。將所獲得之有機層利用水及飽和鹽水洗淨,經無水硫酸鎂乾燥並進行過濾。對濾液進行減壓濃縮,藉由矽膠管柱層析法對所獲得之濃縮物進行精製而獲得目標物0.10 g(產率31%)。
所獲得之目標物之1
H-NMR及19
F-NMR如下所示。1
H-NMR (CDCl3
) δ: 9.94 (1H, d), 9.48 (1H, d), 8.92 (2H, d), 7.52 (1H, s), 7.38 (1H, t), 3.75 (2H, q), 3.70 (3H, s), 1.37 (3H, t);19
F-NMR (376 MHz, CDCl3
-C6
F6
): δ -80.41 (3H, t), -107.20 (2H, q), -125.60--125.68 (2H, m).
[實施例2]
5-(乙基磺醯基)-2-(1-甲基-1H-1,2,4-三唑-3-基)-4-(1-甲基-5-(全氟丁基)-1H-咪唑-2-基)嘧啶[5-(ethylsulfonyl)-2-(1-methyl-1H-1,2,4-triazol-3-yl)-4-(1-methyl-5-(perfluorobutyl)-1H-imidazol-2-yl)pyrimidine](化合物編號a-2)之合成
(步驟1)2-氯-1-(5-碘-1-甲基-1H-咪唑-2-基)乙烷-1-酮[2-chloro-1-(5-iodo-1-methyl-1H-imidazol-2-yl)ethan-1-one]之合成
[化48]
於反應容器中使2,5-二碘-1-甲基-1H-咪唑(34.6 g)溶解於四氫呋喃(1130 ml),對反應容器進行氮氣置換,其後,冷卻至-70℃。於其中滴加正丁基鋰(2.65M,正己烷溶液,42 ml),於-70℃下攪拌30分鐘。於其中添加2-氯-N-甲氧基-N-甲基乙醯胺(17.0 g),於-70℃下攪拌1小時。將所獲得之液體注入至飽和氯化銨水溶液中,利用乙酸乙酯進行萃取。將所獲得之有機層利用飽和鹽水洗淨,經無水硫酸鎂乾燥並進行過濾。對濾液進行減壓濃縮而獲得濃縮物。
(步驟2)2-(乙基硫基)-1-(5-碘-1-甲基-1H-咪唑-2-基)乙烷-1-酮[2-(ethylthio)-1-(5-iodo-1-methyl-1H-imidazol-2-yl)ethan-1-one]之合成
[化49]
使步驟1中獲得之濃縮物(未精製之2-氯-1-(5-碘-1-甲基-1H-咪唑-2-基)乙烷-1-酮)溶解於N,N-二甲基甲醯胺(100 ml)與四氫呋喃(100 ml)之混合溶劑,將所獲得之溶液於0℃下攪拌。於其中添加乙基硫醇鈉(10.0 g,80%),於室溫下攪拌一晩。將所獲得之液體注入至水中,利用乙酸乙酯進行萃取。將所獲得之有機層利用飽和鹽水洗淨,經無水硫酸鎂乾燥並進行過濾。對濾液進行減壓濃縮,藉由矽膠管柱層析法對濃縮物進行精製而獲得目標物5.74 g(產率18%,兩步驟)。
所獲得之目標物之1
H-NMR如下所示。1
H-NMR (400 MHz, CDCl3
): δ 7.28 (1H, s), 4.01 (3H, s), 3.94 (2H, s), 2.64 (2H, q), 1.28 (3H, t).
(步驟3)2-(乙基磺醯基)-1-(5-碘-1-甲基-1H-咪唑-2-基)乙烷-1-酮[2-(ethylsulfonyl)-1-(5-iodo-1-methyl-1H-imidazol-2-yl)ethan-1-one]之合成
[化50]
使2-(乙基硫基)-1-(5-碘-1-甲基-1H-咪唑-2-基)乙烷-1-酮(5.7 g)溶解於二氯甲烷(190 ml),將所獲得之溶液於0℃下攪拌。於其中添加間氯過苯甲酸(70%,10 g),於室溫下攪拌5小時。將所獲得之液體注入至飽和碳酸氫鈉水溶液與飽和硫代硫酸鈉水溶液之混合溶液中,利用二氯甲烷進行萃取。將所獲得之有機層利用飽和鹽水洗淨,經無水硫酸鎂乾燥並進行過濾。對濾液進行減壓濃縮,藉由矽膠管柱層析法對濃縮物進行精製而獲得目標物5.2 g(產率81%)。
所獲得之目標物之1
H-NMR如下所示。1
H-NMR (400 MHz, CDCl3
): δ 7.35 (1H, s), 4.81 (2H, s), 4.02 (3H, s), 3.28 (2H, q), 1.46 (3H, t).
(步驟4)3-(二甲基胺基)-2-(乙基磺醯基)-1-(5-碘-1-甲基-1H-咪唑-2-基)丙-2-烯-1-酮[3-(dimethylamino) -2-(ethylsulfonyl) -1- (5-iodo -1-methyl -1H-imidazol-2-yl) prop-2-en-1-one]之合成
[化51]
使2-(乙基磺醯基)-1-(5-碘-1-甲基-1H-咪唑-2-基)乙烷-1-酮(0.34 g)溶解於四氫呋喃(5 ml),將所獲得之溶液於室溫下攪拌。於其中添加N,N-二甲基甲醯胺二甲基縮醛(0.23 g),於加熱回流下攪拌4小時。對所獲得之液進行減壓濃縮。
(步驟5)5-(乙基磺醯基)-4-(5-碘-1-甲基-1H-咪唑-2-基)-2-(1-甲基-1H-1,2,4-三唑-3-基)嘧啶[5- (ethylsulfonyl) -4-(5-iodo-1- methyl- 1H-imidazol-2-yl)-2-(1-methyl-1H-1,2,4-triazol-3-yl)pyrimidine]之合成
[化52]
使步驟4中獲得之濃縮物(未精製之3-(二甲基胺基)-2-(乙基磺醯基)-1-(5-碘-1-甲基-1H-咪唑-2-基)丙-2-烯-1-酮)溶解於乙醇(10 ml),於室溫下攪拌。於其中添加三乙基胺(0.30 g)與1-甲基-1H-1,2,4-三唑-3-羧基醯亞胺醯胺鹽酸鹽(0.20 g),於加熱回流下攪拌5小時。將所獲得之液體注入至飽和氯化銨水溶液中,利用二氯甲烷進行萃取。將所獲得之有機層利用飽和鹽水洗淨,經無水硫酸鎂乾燥並進行過濾。對濾液進行減壓濃縮,藉由矽膠管柱層析法對所獲得之濃縮物進行精製而獲得目標物0.44 g(產率95%,兩步驟)。
所獲得之目標物之1
H-NMR如下所示。1
H-NMR (400 MHz, CDCl3
): δ 9.50 (1H, s), 8.25 (1H, s), 7.31 (1H, s), 4.11 (3H, s), 4.07 (2H, q), 3.94 (3H, s), 1.41 (3H, t).
(步驟6)5-(乙基磺醯基)-2-(1-甲基-1H-1,2,4-三唑-3-基)-4-(1-甲基-5-(全氟丁基)-1H-咪唑-2-基)嘧啶[5- (ethylsulfonyl) -2-(1-methyl -1H-1,2,4-triazol-3-yl)-4-(1-methyl-5-(perfluorobutyl)-1H-imidazol-2-yl)pyrimidine]之合成
[化53]
於反應容器中使5-(乙基磺醯基)-4-(5碘-1-甲基-1H-咪唑-2-基)-2-(1-甲基-1H-1,2,4-三唑-3-基)嘧啶(0.2 g)溶解於N,N'-二甲基伸丙基脲(3 ml),對反應容器進行氬氣置換,繼而於室溫下攪拌。於其中添加碘化銅(0.17 g)與參考Chem. Eur. J. 2015, 21, 96-100.中記載之方法所合成之雙(正全氟丁基)鋅-DMPU錯合物(0.66 g),於110℃下攪拌3小時。將所獲得之液體注入至飽和羅謝耳鹽水溶液中,利用乙酸乙酯進行萃取。將所獲得之有機層利用水及飽和鹽水洗淨,經無水硫酸鎂乾燥並進行過濾。對濾液進行減壓濃縮,藉由矽膠管柱層析法對所獲得之濃縮物進行精製而獲得目標物0.06 g(產率25%)。
所獲得之目標物之1
H-NMR及19
F-NMR如下所示。1
H-NMR (400 MHz, CDCl3
): δ 9.53 (1H, s), 8.27 (1H, s), 7.54 (1H, s), 4.12 (3H, s), 3.89 (3H, s), 3.88 (2H, q), 1.40 (3H, t);19
F-NMR (376 MHz, CDCl3
-C6
F6
): δ -81.3(s, 3F), -106.3(s, 2F), -121.8(s, 2F), -126.0(s, 2F).
[實施例3]
5-(乙基磺醯基)-4-(4-甲基-5-(九氟丁基)-4H-1,2,4-三唑-3-基)-2,2'-聯嘧啶[5-(ethylsulfonyl)-4-(4-methyl-5-(nonafluorobutyl)-4H-1,2,4-triazol-3-yl)-2,2'-bipyrimidine](化合物編號a-5)之合成
(步驟1)2,2,3,3,4,4,5,5,5-九氟戊醯肼[2,2,3,3,4,4,5,5,5- nonafluoropentanehydrazide]之合成
[化54]
使2,2,3,3,4,4,5,5,5-九氟戊酸乙酯(15.8 g)溶解於甲醇(108 ml),於室溫下攪拌。於其中滴加肼一水合物(2.7 g),於室溫下攪拌30分鐘。對所獲得之液進行減壓濃縮。
(步驟2)N-甲基-2-(2,2,3,3,4,4,5,5,5-九氟戊醯基)肼-1-硫代碳醯胺[N-methyl-2-(2,2,3,3,4,4,5,5,5-nonafluoropentanoyl)hydrazine-1-carbothioamide]之合成
[化55]
使步驟1中獲得之濃縮物(未精製之2,2,3,3,4,4,5,5,5-九氟戊醯肼)16.4 g溶解於甲醇(54 ml),於0℃下攪拌。於其中滴加異硫氰酸甲酯(3.95 g)之甲醇溶液(54 mL),於0℃下攪拌10分鐘。其後,於加熱回流下攪拌3小時。將所獲得之液靜置冷卻至室溫,繼而進行減壓濃縮。
(步驟3)4-甲基-5-(九氟丁基)-2,4-二氫-3H-1,2,4-三唑-3-硫酮[4-methyl-5- (nonafluorobutyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione]之合成
[化56]
使步驟2中獲得之濃縮物(含有未精製之N-甲基-2-(2,2,3,3,4,4,5,5,5-九氟戊醯基)肼-1-硫代碳醯胺)23.5 g懸浮於水(270 ml)中,於室溫下攪拌。於其中添加碳酸氫鈉(45.5 g),於加熱回流下攪拌4小時。將所獲得之液靜置冷卻至室溫,其後,利用濃鹽酸將pH值調整至2,利用乙酸乙酯進行萃取。將所獲得之有機層利用飽和鹽水洗淨,經無水硫酸鎂乾燥並進行過濾。對濾液進行減壓濃縮。
(步驟4)4-甲基-3-(九氟丁基)-4H-1,2,4-三唑[4-methyl-3- (nonafluorobutyl) -4H-1,2,4-triazole]之合成
[化57]
使步驟3中獲得之濃縮物(含有4-甲基-5-(九氟丁基)-2,4-二氫-3H-1,2,4-三唑-3-硫酮)15.7 g懸浮於水(424 ml)中,於室溫下攪拌。於其中添加硝酸(47 ml),於加熱回流下攪拌4小時。將所獲得之液靜置冷卻至室溫,繼而於冰浴冷卻下利用30%氫氧化鈉水溶液將pH值調整至12,利用氯仿進行萃取。將所獲得之有機層利用經無水硫酸鎂乾燥並進行過濾。對濾液進行減壓濃縮,藉由矽膠管柱層析法對所獲得之濃縮物進行精製而獲得目標物10.5 g(產率75%,四步驟)。
所獲得之目標物之1
H-NMR如下所示。1
H-NMR (400 MHz, CDCl3
): δ 8.25 (s, 1H), 3.86 (s, 3H).
(步驟5)3-溴-4-甲基-5-(九氟丁基)-4H-1,2,4-三唑[3-bromo-4-methyl-5- (nonafluorobutyl)-4H-1,2,4-triazole]之合成
[化58]
使4-甲基-3-(九氟丁基)-4H-1,2,4-三唑(3.44 g)溶解於四氯化碳(114 mL),於室溫下攪拌。於其中添加N-溴丁二醯亞胺(2.24 g),於加熱回流下攪拌20小時。將所獲得之液靜置冷卻至室溫,繼而進行減壓濃縮。藉由矽膠管柱層析法對所獲得之濃縮物進行精製而獲得目標物2.49 g(產率57%)。
所獲得之目標物之1
H-NMR如下所示。1
H-NMR (400 MHz, CDCl3
): δ 3.79 (s, 3H).
(步驟6)2-氯-1-(4-甲基-5-(九氟丁基)-4H-1,2,4-三唑-3-基)乙烷-1-酮[2-chloro-1-(4-methyl-5-(nonafluorobutyl)-4H-1,2,4-triazol-3-yl)ethan-1-one]之合成
[化59]
使3-溴-4-甲基-5-(九氟丁基)-4H-1,2,4-三唑(1.50 g)溶解於四氫呋喃(16 ml),將反應系內進行氮氣置換後,冷卻至-72℃。於其中滴加正丁基鋰(2.76M,正己烷溶液,1.70 ml),於-72℃下攪拌30分鐘。於其中滴加2-氯-N-甲氧基-N-甲基乙醯胺(0.652 g)之四氫呋喃溶液(4 ml),於-72℃下攪拌1小時。將所獲得之液體注入至飽和氯化銨水溶液中,利用乙酸乙酯進行萃取。將所獲得之有機層利用飽和鹽水洗淨,經無水硫酸鎂乾燥並進行過濾。對濾液進行減壓濃縮,藉由矽膠管柱層析法對所獲得之濃縮物進行精製而獲得目標物0.90 g(產率60%)。
所獲得之目標物之1
H-NMR如下所示。1
H-NMR (400 MHz, CDCl3
): δ 5.04 (s, 2H), 4.13 (s, 3H).
(步驟7)2-(乙基硫基)-1-(4-甲基-5-(九氟丁基)-4H-1,2,4-三唑-3-基)乙烷-1-酮[2-(ethylthio) -1-(4-methyl-5- (nonafluorobutyl) -4H-1,2,4-triazol -3-yl)ethan-1-one]之合成
[化60]
使2-氯-1-(4-甲基-5-(九氟丁基)-4H-1,2,4-三唑-3-基)乙烷-1-酮(0.90 g)溶解於四氫呋喃(24 ml),於室溫下攪拌。於其中添加乙基硫醇鈉(90%,0.245 g),於室溫下攪拌6小時。於其中追加乙基硫醇鈉(90%,0.245 g),於室溫下攪拌1小時。將所獲得之液體注入至飽和氯化銨水溶液中,利用乙酸乙酯進行萃取。將所獲得之有機層利用飽和鹽水洗淨,經無水硫酸鎂乾燥並進行過濾。對濾液進行減壓濃縮。
(步驟8)2-(乙基磺醯基)-1-(4-甲基-5-(九氟丁基)-4H-1,2,4-三唑-3-基)乙烷-1-酮[2-(ethylsulfonyl) -1-(4-methyl-5- (nonafluorobutyl) -4H-1,2,4 -triazol-3-yl)ethan-1-one]之合成
[化61]
使步驟7中獲得之濃縮物(含有2-(乙基硫基)-1-(4-甲基-5-(九氟丁基)-4H-1,2,4-三唑-3-基)乙烷-1-酮)0.98 g溶解於二氯甲烷(24 ml),於0℃下攪拌。於其中添加間氯過苯甲酸(70%,1.32 g),於室溫下攪拌3小時。將所獲得之液體注入至飽和碳酸氫鈉水溶液與飽和硫代硫酸鈉水溶液之混合溶液中,利用氯仿進行萃取。將所獲得之有機層利用經無水硫酸鎂乾燥並進行過濾。對濾液進行減壓濃縮。藉由矽膠管柱層析法對所獲得之濃縮物進行精製而獲得目標物0.807 g(產率78%,兩步驟)。
所獲得之目標物之1
H-NMR如下所示。1
H-NMR (400 MHz, CDCl3
): δ 4.92 (s, 2H), 4.11 (s, 3H), 3.31 (q, 2H), 1.48 (t, 3H).
(步驟9)3-(二甲基胺基)-2-(乙基磺醯基)-1-(4-甲基-5-(九氟丁基)-4H- 1,2,4-三唑-3-基)丙-2-烯-1-酮[3-(dimethylamino)-2- (ethylsulfonyl) -1-(4-methyl-5-(nonafluorobutyl)-4H-1,2,4-triazol-3-yl)prop-2-en-1-one]之合成
[化62]
使2-(乙基磺醯基)-1-(4-甲基-5-(九氟丁基)-4H-1,2,4-三唑-3-基)乙烷-1-酮(0.20 g)溶解於四氫呋喃(2.3 ml),於室溫下攪拌。於其中添加N,N-二甲基甲醯胺二甲基縮醛(0.274 g),於加熱回流下攪拌1.5小時。對所獲得之液進行減壓濃縮。
(步驟10)5-(乙基磺醯基)-4-(4-甲基-5-(九氟丁基)-4H-1,2,4-三唑-3-基)-2,2'-聯嘧啶[5- (ethylsulfonyl) -4-(4-methyl-5- (nonafluorobutyl)-4H -1,2,4-triazol-3-yl)-2,2'-bipyrimidine]之合成
[化63]
使步驟9中獲得之濃縮物(含有3-(二甲基胺基)-2-(乙基磺醯基)-1-(4-甲基-5-(九氟丁基)-4H-1,2,4-三唑-3-基)丙-2-烯-1-酮)0.27 g溶解於乙醇(2.3 ml),於室溫下攪拌。於其中添加三乙基胺(0.209 g)與2-脒基嘧啶鹽酸鹽(0.109 g),於加熱回流下攪拌1小時。將所獲得之液體注入至飽和氯化銨水溶液中,利用氯仿進行萃取。將所獲得之有機層利用經無水硫酸鎂乾燥並進行過濾。對濾液進行減壓濃縮,藉由矽膠管柱層析法對所獲得之濃縮物進行精製而獲得目標物0.10 g(產率40%,兩步驟)。
所獲得之目標物之1
H-NMR及19
F-NMR如下所示。1
H-NMR (400 MHz, CDCl3
): δ 9.70 (s, 1H), 9.09 (d, 2H), 7.56 (t, 1H), 3.92 (s, 3H), 3.83 (q, 2H), 1.42 (t, 3H);19
F-NMR (376 MHz, CDCl3
-C6
F6
): δ -81.28 (t, 3F), -109.73 (t, 2F), -122.00 - -122.09 (m, 2F), -125.72 - -125.81 (m, 2F).
將藉由與上述實施例相同之方法所製造之本發明化合物之一部分示於表1~表3。表1中顯示式(I)所表示之化合物之取代基。於表中一併顯示作為各化合物之物性的性狀、熔點(m.p.)或折射率(nD
)。
再者,表中之Me表示甲基、Et表示乙基、c
Pr表示環丙基、Ac表示乙醯基。
[表1]
[化64]
[表2]
化合物編號 | (X)n | R1 | R2 | R | 物性 |
b-1 | 5-c Pr | SO2 Et | Me | CF2 CF2 CF2 CF3 | m.p.:138-140(℃) |
b-2 | - | SEt | Me | CF2 CF2 CF2 CF3 | nd(20.8℃):1.4817 |
b-3 | - | SO2 Et | Me | CF2 CF2 CF2 CF3 | m.p.:83-85(℃) |
b-4 | 5-( 嘧啶-2-基) | SO2 Et | Me | CF2 CF2 CF2 CF3 | m.p.:114-116(℃) |
b-5 | 6-(1H-1,2,4-三唑-1-基) | SO2 Et | Me | CH(OAc)CF2 CF2 CF2 CF3 | m.p.:183-185(℃) |
b-6 | 6-(1H-1,2,4-三唑-1-基) | SO2 Et | Me | CH(OH)CF2 CF2 CF2 CF3 | m.p.:179-181(℃) |
b-7 | 5-CF3 | SO2 Et | Me | CF2 CF2 CF2 CF3 | m.p.:88-90(℃) |
b-8 | 6-(1H-1,2,4-三唑-1-基) | SO2 Et | Me | CF2 CF2 CF2 CF3 | m.p.:129-131(℃) |
b-9 | 6-( 嘧啶-2-基) | SO2 Et | Me | CF2 CF2 CF2 CF3 | m.p.:125-127(℃) |
b-10 | 6-(1H-1,2,4- 三唑-1-基) | SO2 Et | Me | CHFCF2 CF2 CF2 CF3 | m.p.:143-145(℃) |
b-11 | - | SO2 Et | Me | CHFCF2 CF2 CF2 CF3 | m.p.:78-80(℃) |
b-12 | 6-NH2 | SO2 Et | Me | CF2 CF2 CF2 CF3 | m.p.:53-55(℃) |
b-13 | 6-(1H-1,2,4-三唑-1-基) | SO2 Et | Me | CCIHCF2 CF2 CF2 CF3 | m.p.:162-164(℃) |
b-14 | - | SO2 Et | Me | CCIHCF2 CF2 CF2 CF3 | m.p.:94-96(℃) |
b-15 | 5-CF3 | SO2 Et | Me | CF2 CF2 CF3 | m.p.:109-110(℃) |
b-16 | 6-(1H-1,2,4-三唑-1-基) | SO2 Et | Me | CF2 CF2 CF3 | m.p.:147-149(℃) |
b-17 | 6-(1H-1,2,4-三唑-1-基) | SO2 Et | Me | CF2 CF3 | m.p.:151-152(℃) |
b-18 | 5-c Pr | SO2 Et | Me | CHFCF2 CF2 CF3 | m.p.:106-108(℃) |
b-19 | 5-( 嘧啶-2-基) | SO2 Et | Me | CF2 CF2 CF3 | m.p.:133-135(℃) |
b-20 | 5-c Pr | SO2 Et | Me | CF2 CF2 CF3 | m.p.:118-120(℃) |
b-21 | 5-(嘧啶-2-基) | SO2 Et | Me | CHFCF2 CF2 CF3 | m.p.:164-167(℃) |
b-22 | 5-(嘧啶-2-基) | SO2 Et | Me | CF2 CF3 | m.p.:148-150(℃) |
b-23 | 5-Br | SO2 Et | Me | CHFCF2 CF3 | m.p.:177-180(℃) |
b-24 | 5-(嘧啶- 2-基) | SO2 Et | Me | CHFCF2 CF3 | m.p.:170-173(℃) |
b-25 | 5-c Pr | SO2 Et | Me | CHFCF2 CF3 | m.p.:130-132(℃) |
b-26 | 5-c Pr | SO2 Et | Me | CF2 CF3 | m.p.:148-150(℃) |
b-27 | 5-( 吡啶-2-基) | SO2 Et | Me | CHFCF2 CF3 | m.p.:128-131(℃) |
b-28 | 5-(1H-1,2,4-三唑-1-基) | SO2 Et | Me | CHFCF2 CF3 | 非晶形 |
b-29 | 5-(吡啶-2-基) | SO2 Et | Me | CF2 CF2 CF3 | m.p.:116-118(℃) |
b-30 | 5-(1-CN-2-OEt-2-側氧基乙基) | SO2 Et | Me | CF2 CF2 CF3 | m.p.:164-166(℃) |
b-31 | 5-( 嘧啶-2-基) | SO2 Et | Me | CHFCF(CF3 )2 | 白色固體 |
b-32 | 5-(嘧啶-2-基) | SO2 Et | Me | CHCICF2 CF3 | m.p.:149-151(℃) |
b-33 | 5-(噻唑-2-基) | SO2 Et | Me | CHFCF2 CF3 | m.p.:138-141(℃) |
b-34 | 5-(3,5-F2 -苯基) | SO2 Et | Me | CHFCF2 CF3 | m.p.:134-136(℃) |
b-35 | 5-(嘧啶-5-基) | SO2 Et | Me | CHFCF2 CF3 | m.p.:128-131(℃) |
b-36 | 5-(3-CF3 -1H-吡唑-1-基) | SO2 Et | Me | CF2 CF2 CF3 | m.p.:111-113(℃) |
b-37 | 5-( 吡啶-2-基氧基) | SO2 Et | Me | CF2 CF2 CF3 | 稠油 |
b-38 | 5-(2-側氧基吡啶-1(2H)-基) | SO2 Et | Me | CF2 CF2 CF3 | m.p.:147-150(℃) |
b-39 | 5-乙烯基 | SO2 Et | Me | CHFCF2 CF3 | m.p.:128-130(℃) |
b-40 | 5-甲醯基 | SO2 Et | Me | CHFCF2 CF3 | 稠油 |
b-41 | 5-(NHCOc Pr) | SO2 Et | Me | CF2 CF2 CF3 | m.p.:215-217(℃) |
b-42 | 5-(2-CN- 丙-2-基) | SO2 Et | Me | CF2 CF2 CF3 | m.p.:138-140(℃) |
b-43 | 5-( 吡啶-2-基) | SO2 Et | Me | CHFCF(CF3 )2 | m.p.:141-143(℃) |
b-44 | 5-(吡啶-2-基) | SO2 Et | Me | CHCICF(CF3 )2 | m.p.:160-162(℃) |
b-45 | 5-(1H-1,2,4-三唑-1-基) | SO2 Et | Me | CF2 CF2 CF3 | m.p.:145-147(℃) |
b-46 | 6-(嘧啶-2-基) | SO2 Et | Me | CHFCF(CF3 )2 | m.p.:145-147(℃) |
b-47 | 6-(1H-1,2,4-三唑-1-基) | SO2 Et | Me | CHFCF(CF3 )2 | m.p.:141-143(℃) |
b-48 | 5-(嘧啶-2-基) | SO2 Et | Me | CH2 CH(CF3 )2 | m.p.:184-187(℃) |
b-49 | 5-CF3 | SO2 Et | Me | CHFCF(CF3 )2 | m.p.:122-124(℃) |
b-50 | - | SO2 Et | Me | CHFCF(CF3 )2 | m.p.:94-97(℃) |
b-51 | 5-(1-CN-c Pr) | SO2 Et | Me | CF2 CF2 CF3 | m.p.:158-160(℃) |
b-52 | 5-c Pr | SO2 Et | Me | CHFCF(CF3 )2 | m.p.:125-127(℃) |
b-53 | 5-c Pr | SO2 Et | Me | CHCICF(CF3 )2 | m.p.:123-125(℃) |
b-54 | 5-(3-CN-吡啶-2-基) | SO2 Et | Me | CF2 CF2 CF3 | m.p.:118-120(℃) |
b-55 | 5-(3-F-吡啶-2-基) | SO2 Et | Me | CF2 CF2 CF3 | m.p.:161-163(℃) |
b-56 | 5-(1-CN-c Pr) | SO2 Et | Me | CHFCF(CF3 )2 | 非晶形 |
b-57 | 5-(1-(吡啶-2-基)-c Pr) | SO2 Et | Me | CHFCF(CF3 )2 | m.p.:71-75(℃) |
b-58 | 5-(2-F-苯基) | SO2 Et | Me | CF2 CF2 CF3 | m.p.:128-130(℃) |
b-59 | 5-(吡啶-2-基) | SO2 Et | Me | CF2 CF2 CF2 CF3 | m.p.:90-92(℃) |
b-60 | 5-(3,5-F2 -苯基) | SO2 Et | Me | CF2 CF2 CF3 | m.p.:133-135(℃) |
b-61 | 5-(3-F-吡啶-2-基) | SO2 Et | Me | CF2 CF2 CF2 CF3 | m.p.:124-126(℃) |
b-62 | 5-(3-Cl-吡啶-2-基) | SO2 Et | Me | CF2 CF2 CF3 | m.p.:138-140(℃) |
b-63 | 5-c Pr | SO2 Et | Me | CHFCF2 CF2 CF2 CF3 | m.p.:135-138(℃) |
b-64 | 5-(嘧啶-2-基) | SO2 Et | Me | CHFCF2 CF2 CF2 CF3 | m.p.:170-172(℃) |
b-65 | 5-c Pr | SO2 Et | Me | CH2 CH(CF3 )2 | 稠油 |
b-66 | 5-(吡啶-2-基) | SO2 Et | Me | CHFCF2 CF2 CF2 CF3 | m.p.:71-75(℃) |
b-67 | 5-(嘧啶-2-基) | SO2 Et | Me | CHFCH2 CH2 CF3 | 白色固體 |
b-68 | 5-(OCH2 CF2 CF3 ) | SO2 Et | Me | CHFCF(CF3 )2 | nD (21.6℃)1.4513 |
b-69 | 5-(OCMe2 CF3 ) | SO2 Et | Me | CHFCF(CF3 )2 | m.p.:71-75(℃) |
b-70 | 5-c Pr | SO2 Et | Me | CH2 OCH2 CF2 CF3 | m.p.:71-75(℃) |
b-71 | 5-c Pr | SO2 Et | Me | CH2 OCH2 CF2 CF2 CF3 | m.p.:71-75(℃) |
b-72 | 5-c Pr | SO2 Et | Me | CH2 OCF2 CHFOCF3 | 稠油 |
[表3]
關於表1~表3所示之化合物中之稠油(viscous oil)、非晶形(amorphous)或白色固體(white solid)之性狀之化合物,將1
H-NMR資料示於以下。
化合物編號a-10:1
H-NMR (CDCl3
) δ: 9.55 (1H, s), 8.10 (1H, s), 7.56 (1H, s), 4.44 (3H, s), 3.93 (2H, q), 3.91 (3H, s), 1.42 (3H, t).
化合物編號b-28:1
H-NMR (400 MHz, CDCl3
) δ: 9.37 (d, 1H), 8.80 (s, 1H), 8.78 (d, 1H), 8.25 (s, 1H), 7.44 (d, 1H), 5.92 (ddd, 1H), 3.88 (q, 2H), 3.70 (s, 3H), 1.38 (t, 3H).
化合物編號b-31:1
H-NMR (400 MHz, CDCl3
) δ: 9.93 (d, 1H), 9.47 (d, 1H), 8.91 (d, 2H), 7.40 (dd, 1H), 7.37 (t, 1H), 6.10 (ddd, 1H), 3.80 (q, 2H), 3.67 (d, 3H), 1.37 (t, 3H).
化合物編號b-37:1
H-NMR (400 MHz, CDCl3
) δ: 8.83 (d, 1H), 8.31 (d, 1H), 8.19 (dd, 2H), 7.83 (dt, 1H), 7.50 (s, 1H), 7.16 (dd, 1H), 7.12 (d, 1H), 3.70 (q, 2H), 3.67 (s, 3H), 1.33 (t, 3H).
化合物編號b-40:1
H-NMR (400 MHz, CDCl3
) δ: 10.28 (s, 1H), 9.35 (d, 1H), 8.92 (d, 1H), 7.45 (d, 1H), 5.90 (ddd, 1H), 3.96-3.86 (m, 2H), 3.74 (s, 3H), 1.37 (t, 3H).
化合物編號b-56:1
H-NMR (400 MHz, CDCl3
) δ: 8.99 (1H, d), 8.19 (1H, d), 7.37 (1H, dd), 6.08 (1H, dd), 3.76 (2H, q), 3.62 (3H, s), 2.00 (2H, dd), 1.63 (2H, dd), 1.31 (3H, t).
化合物編號b-65:1
H-NMR (400 MHz, CDCl3
) δ: 8.67 (1H, d), 8.01 (1H, d), 7.01 (1H, s), 3.71 (2H, q), 3.49 (3H, s), 3.30-3.17 (3H, m), 2.10-2.03 (1H, m), 1.28 (3H, t), 1.24-1.19 (2H, m), 0.93-0.88 (2H, m).
化合物編號b-67:1
H-NMR (400 MHz, CDCl3
) δ: 9.91 (1H, d), 9.47 (1H, d), 8.91 (2H, d), 7.36 (1H, t), 7.23 (1H, d), 5.59 (1H, ddd), 3.92-3.80 (2H, m), 3.69 (3H, s), 2.56-2.33 (4H, m), 1.38 (3H, t).
化合物編號b-72:1
H-NMR (400 MHz, CDCl3
) δ: 8.68 (1H, d), 8.02 (1H, d), 7.21 (1H, s), 5.76 (1H, dt), 5.09 (2H, s), 3.74 (2H, q), 3.55 (3H, s), 2.11-2.05 (1H, m), 1.30 (3H, t), 1.25-1.16 (2H, m), 0.96-0.89 (2H, m).
化合物編號c-2:1
H-NMR (400 MHz, CDCl3
) δ: 9.31 (d, 1H), 8.89 (d, 1H), 7.58 (s, 1H), 7.43 (d, 1H), 5.91 (ddd, 1H), 4.79 (t, 2H), 3.89-3.78 (m, 2H), 3.71 (s, 3H), 1.34 (t, 3H).
[生物試驗]
藉由以下之試驗例表明本發明之雜芳基唑化合物作為有害生物防除劑及外部寄生蟲防除劑之有效成分有用。再者,「份」為重量基準。
(試驗用乳劑之製備)
將本發明雜芳基唑化合物5份、二甲基甲醯胺93.6份及聚氧乙烯烷基芳基醚1.4份進行混合溶解,而製備有效成分5%之乳劑(I)。
作為對照,將二甲基甲醯胺98.5份及聚氧乙烯烷基芳基醚1.5份進行混合溶解,而製備乳劑(II)。
藉由下式計算殺蟲率。
殺蟲率(%)=(死亡蟲數/試驗蟲數)×100
(試驗例1)對黏夜蛾之效力試驗
將市售之人工飼料(Insecta LFS,日本農產工業公司製造)0.8 g與乳劑(I)1 μl充分混合而獲得試驗用飼料。
於塑膠製試驗容器(容積1.4 ml)中,每處理區各裝0.2 g之試驗用飼料。繼而,每處理區各接種2隻黏夜蛾二齡幼蟲。對試驗容器蓋上塑膠製之蓋子以防黏夜蛾二齡幼蟲逃跑。將其置於25℃之恆溫室內,於第5天調查殺蟲率與攝食量。反覆進行2次試驗。
作為對照區,將乳劑(I)變為乳劑(II),除此以外,藉由與試驗例1相同之方法調查殺蟲率與攝食量。
針對化合物編號a-1、a-2、a-6、a-8、a-9、b-1、b-2、b-3、b-4、b-7、b-8、b-9、b-10、b-11、b-12、b-13、b-15、b-16、b-17、b-18、b-20、b-22、b-23、b-24、b-25、b-26、b-27、b-29、b-32、b-34、b-35、b-36、b-39、b-41、b-42、b-43、b-44、b-45、b-52、b-53、b-54、b-55、b-57、b-58、b-59、b-60、b-61、b-62、b-63、b-64、b-66、b-68、b-69、c-1、c-5及c-8之化合物,進行對黏夜蛾之效力試驗。各化合物均對黏夜蛾之殺蟲率為100%、或攝食量相對於對照區為10%以下。可知本發明雜芳基唑化合物對黏夜蛾有效。
(試驗例2)對黏夜蛾之效力試驗
用水稀釋乳劑(I)以使本發明化合物之濃度成為125 ppm。將玉米葉於上述稀釋液中浸漬30秒。將該玉米葉放入培養皿中,投放5隻黏夜蛾二齡幼蟲。將培養皿置於溫度25℃、濕度60%之恆溫室內。於放蟲後經過6天時判定生死,算出殺蟲率。反覆進行2次試驗。
針對化合物編號a-2、b-4、b-18、b-19及b-21之化合物,進行對黏夜蛾之效力試驗。各化合物均對黏夜蛾顯示出80%以上之殺蟲率。
(試驗例3)對小菜蛾之效力試驗
用水稀釋乳劑(I)以使本發明化合物之濃度成為125 ppm。將甘藍葉於上述稀釋液中浸漬30秒。將該甘藍葉放入培養皿中。於其中投放5隻小菜蛾二齡幼蟲。將培養皿置於溫度25℃、濕度60%之恆溫室內。於放蟲後經過3天時判定生死,算出殺蟲率。反覆進行2次試驗。
針對化合物編號a-1、a-2、a-4、a-5、a-6、a-10、b-1、b-4、b-8、b-9、b-10、b-13、b-15、b-16、b-18、b-19、b-20、b-21、b-22、b-24、b-25、b-27、b-29、b-31、b-34、b-36、b-37、b-41、b-42、b-43、b-44、b-45、b-47、b-48、b-51、b-52、b-54、b-55、b-56、b-58、b-60、b-61、b-62、b-64、b-67、b-69、c-1、c-4及c-5之化合物,進行對小菜蛾之效力試驗。各化合物均對小菜蛾顯示出80%以上之殺蟲率。
(試驗例4)對斜紋夜蛾之效力試驗
用水稀釋乳劑(I)以使本發明化合物之濃度成為125 ppm。將甘藍葉於上述稀釋液中浸漬30秒。將該甘藍葉放入培養皿中。於其中投放5隻斜紋夜蛾二齡幼蟲。將培養皿置於溫度25℃、濕度60%之恆溫室內。於放蟲後經過6天時判定生死,算出殺蟲率。反覆進行2次試驗。
針對化合物b-18、b-20、b-21及b-51之化合物,進行對斜紋夜蛾之效力試驗。各化合物均對斜紋夜蛾顯示出80%以上之殺蟲率。
(試驗例5)對豆蚜之效力試驗
於3寸缽中培育豇豆幼苗,對初生葉上接種豆蚜若蟲。用水稀釋乳劑(I)以使本發明化合物之濃度成為125 ppm,在豆蚜若蟲所寄生之豇豆上散佈上述稀釋液。將該豇豆置於溫度25℃、濕度60%之恆溫室內。於散佈後經過4天時判定豆蚜之生死,算出殺蟲率。反覆進行2次試驗。
針對化合物編號a-1、a-2、a-6、a-9、b-1、b-2、b-3、b-4、b-7、b-8、b-9、b-11、b-12、b-15、b-16、b-17、b-18、b-20、b-22、b-23、b-24、b-25、b-26、b-27、b-29、b-32、b-35、b-36、b-38、b-40、b-41、b-42、b-43、b-44、b-45、b-52、b-53、b-54、b-55、b-57、b-58、b-59、b-60、b-61、b-62、b-63、b-64、b-66、b-69、b-70、b-71、c-7及c-8之化合物,進行對豆蚜之效力試驗。各化合物均對豆蚜顯示出80%以上之殺蟲率。
(試驗例6)對黃條葉蚤之效力試驗
用水稀釋乳劑(I)以使本發明化合物之濃度成為125 ppm,而製備試驗用藥液。對種植於3寸缽中之青梗菜苗(第7片葉展開期)散佈上述試驗用藥液。風乾後,將青梗菜苗放入塑膠杯中。於其中投放10隻黃條葉蚤(Phyllotreta striolata)成蟲。於溫度25℃、濕度65%之恆溫室內保管,放蟲7天後判定生死,算出殺蟲率。反覆進行2次試驗。
針對化合物編號a-1、a-2、a-6、b-1、b-4、b-8、b-9、b-18、b-19、b-21、b-22、b-24、b-29、b-31、b-34、b-37、b-43、b-48、b-52、b-55、b-58、b-59、b-61、b-62、b-69、c-1、c-2及c-5之化合物,進行對黃條葉蚤成蟲之效力試驗。各化合物均對黃條葉蚤成蟲顯示出80%以上之殺蟲率。
(試驗例7)對黃條葉蚤之效力試驗
用水稀釋乳劑(I)以使本發明化合物之濃度成為2 ppm,而製備試驗用藥液。對種植於3寸缽中之青梗菜苗(第7片葉展開期)散佈上述試驗用藥液。風乾後,將青梗菜苗放入塑膠杯中。於其中投放10隻黃條葉蚤(Phyllotreta striolata)成蟲。於溫度25℃、濕度65%之恆溫室內保管,放蟲7天後判定生死,算出殺蟲率。反覆進行2次試驗。
針對化合物編號a-1、a-2、a-6、b-1、b-4、b-8、b-18、b-19、b-21、b-24、b-29、b-31、b-34、b-43、b-48、b-52、b-55、b-58、b-59、b-61、b-62及c-1之化合物,進行對黃條葉蚤成蟲之效力試驗。各化合物均對黃條葉蚤成蟲顯示出80%以上之殺蟲率。
(試驗例8)對褐飛虱之效力試驗
用水稀釋乳劑(I)以使本發明化合物之濃度成為125 ppm。將稻幼苗於該稀釋液中浸漬30秒。風乾後,將稻幼苗放入塑膠箱中。於其中投放5隻褐飛虱二齡幼蟲。於溫度25℃、濕度65%之恆溫室內保管,接種7天後判定生死,算出殺蟲率。反覆進行2次試驗。
針對化合物編號a-1、a-2、a-3、a-4、a-9、b-3、b-4、b-7、b-9、b-15、b-17、b-19、b-28、b-34、b-46、b-47、b-48、b-51及b-67之化合物,進行對褐飛虱之效力試驗。各化合物均對褐飛虱顯示出80%以上之殺蟲率。
(試驗例9)對家蠅之效力試驗
用丙酮稀釋本發明化合物後滴至1 g方糖上,使濃度成為100 ppm。將該方糖放入塑膠杯中,投放10隻家蠅(Musca domestica)雌成蟲,蓋上蓋子。於25℃下保管,放蟲24小時後判定生死,算出殺蟲率。反覆進行2次試驗。
針對化合物編號b-4之化合物,進行對家蠅之效力試驗。各化合物均對家蠅顯示出80%以上之殺蟲率。
自本發明之雜芳基唑化合物之中隨機選擇者均發揮如上所述之效果,由此可理解本發明之雜芳基唑化合物包括未盡數例示之化合物在內為具備有害生物防除、尤其是殺蟎、殺蟲等效果之化合物。又,可理解為亦對外部寄生蟲等危害人畜之寄生蟲有效果之化合物。
Claims (10)
- 一種有害生物防除劑,其含有選自由如請求項1之化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物及該等之鹽所組成之群中之至少一種作為有效成分。
- 一種殺蟲或殺蟎劑,其含有選自由如請求項1之化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物及該等之鹽所組成之群中之至 少一種作為有效成分。
- 一種外部寄生蟲防除劑,其含有選自由如請求項1之化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物及該等之鹽所組成之群中之至少一種作為有效成分。
- 一種內部寄生蟲防除劑或驅除劑,其含有選自由如請求項1之化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物及該等之鹽所組成之群中之至少一種作為有效成分。
- 一種種子處理劑或營養繁殖器官處理劑,其含有選自由如請求項1之化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物及該等之鹽所組成之群中之至少一種作為有效成分。
- 一種水稻育苗箱處理用農藥粒狀組成劑,其含有選自由如請求項1之化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物及該等之鹽所組成之群中之至少一種作為有效成分。
- 一種土壤處理劑,其含有選自由如請求項1之化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物及該等之鹽所組成之群中之至少一種作為有效成分。
- 一種餌劑,其含有選自由如請求項1之化合物、其N-氧化物化合物、 立體異構物、互變異構物、水合物及該等之鹽所組成之群中之至少一種作為有效成分。
- 一種植物生長促進劑,其含有選自由如請求項1之化合物、其N-氧化物化合物、立體異構物、互變異構物、水合物及該等之鹽所組成之群中之至少一種作為有效成分。
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