JP5069679B2 - カルボキサミド類 - Google Patents
カルボキサミド類 Download PDFInfo
- Publication number
- JP5069679B2 JP5069679B2 JP2008515089A JP2008515089A JP5069679B2 JP 5069679 B2 JP5069679 B2 JP 5069679B2 JP 2008515089 A JP2008515089 A JP 2008515089A JP 2008515089 A JP2008515089 A JP 2008515089A JP 5069679 B2 JP5069679 B2 JP 5069679B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- carboxamide
- trifluoromethyl
- alkyl
- pyrazole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000003857 carboxamides Chemical class 0.000 title claims description 18
- 244000068988 Glycine max Species 0.000 claims description 16
- 241000682645 Phakopsora pachyrhizi Species 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 230000009261 transgenic effect Effects 0.000 claims description 6
- GZNCWLFUAXRBFQ-UHFFFAOYSA-N 1-methyl-n-[2-(4-methylpentan-2-yl)phenyl]-4-(trifluoromethyl)pyrrole-3-carboxamide Chemical compound CC(C)CC(C)C1=CC=CC=C1NC(=O)C1=CN(C)C=C1C(F)(F)F GZNCWLFUAXRBFQ-UHFFFAOYSA-N 0.000 claims description 3
- VNBSGTZYDLJUTQ-UHFFFAOYSA-N 5-chloro-1,3-dimethyl-n-[2-(4-methylpentan-2-yl)phenyl]pyrazole-4-carboxamide Chemical compound CC(C)CC(C)C1=CC=CC=C1NC(=O)C1=C(Cl)N(C)N=C1C VNBSGTZYDLJUTQ-UHFFFAOYSA-N 0.000 claims description 3
- GOFJDXZZHFNFLV-UHFFFAOYSA-N 5-fluoro-1,3-dimethyl-N-[2-(4-methylpentan-2-yl)phenyl]pyrazole-4-carboxamide Chemical compound CC(C)CC(C)C1=CC=CC=C1NC(=O)C1=C(F)N(C)N=C1C GOFJDXZZHFNFLV-UHFFFAOYSA-N 0.000 claims description 3
- OCQFSYGUABRLOC-UHFFFAOYSA-N 5-fluoro-1-methyl-n-[2-(4-methylpentan-2-yl)phenyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound CC(C)CC(C)C1=CC=CC=C1NC(=O)C1=C(F)N(C)N=C1C(F)(F)F OCQFSYGUABRLOC-UHFFFAOYSA-N 0.000 claims description 3
- LDLMOOXUCMHBMZ-UHFFFAOYSA-N bixafen Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=C(F)C=C1C1=CC=C(Cl)C(Cl)=C1 LDLMOOXUCMHBMZ-UHFFFAOYSA-N 0.000 claims description 3
- HEQWTZGQCWAMBQ-UHFFFAOYSA-N n-[2-(4-chloro-3-fluorophenyl)phenyl]-2-methyl-4-(trifluoromethyl)-1,3-thiazole-5-carboxamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=CC=CC=C1C1=CC=C(Cl)C(F)=C1 HEQWTZGQCWAMBQ-UHFFFAOYSA-N 0.000 claims description 3
- JHPLCHZJZZSZGU-KIBLKLHPSA-N n-[2-[3-fluoro-4-[(e)-methoxyiminomethyl]phenyl]phenyl]-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1=C(F)C(/C=N/OC)=CC=C1C1=CC=CC=C1NC(=O)C1=CN(C)N=C1C(F)(F)F JHPLCHZJZZSZGU-KIBLKLHPSA-N 0.000 claims description 3
- RLOWEOUQZWVGBV-UHFFFAOYSA-N 1,3-dimethyl-n-[2-(4-methylpentan-2-yl)phenyl]pyrazole-4-carboxamide Chemical compound CC(C)CC(C)C1=CC=CC=C1NC(=O)C1=CN(C)N=C1C RLOWEOUQZWVGBV-UHFFFAOYSA-N 0.000 claims description 2
- PFFIDZXUXFLSSR-UHFFFAOYSA-N 1-methyl-N-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound S1C=CC(NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)=C1C(C)CC(C)C PFFIDZXUXFLSSR-UHFFFAOYSA-N 0.000 claims description 2
- KKJAYAKCRSKZKO-UHFFFAOYSA-N 1-methyl-n-[3-(4-methylphenyl)thiophen-2-yl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1=CC(C)=CC=C1C1=C(NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)SC=C1 KKJAYAKCRSKZKO-UHFFFAOYSA-N 0.000 claims description 2
- IKOOGXUHKYHAEJ-UHFFFAOYSA-N 3-(difluoromethyl)-1-methyl-n-[2-(4-methylpentan-2-yl)phenyl]pyrazole-4-carboxamide Chemical compound CC(C)CC(C)C1=CC=CC=C1NC(=O)C1=CN(C)N=C1C(F)F IKOOGXUHKYHAEJ-UHFFFAOYSA-N 0.000 claims description 2
- MVKCRDFUMXKDAJ-UHFFFAOYSA-N 3-(difluoromethyl)-n-[2-(3,3-dimethylbutyl)phenyl]-1-methylpyrazole-4-carboxamide Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1CCC(C)(C)C MVKCRDFUMXKDAJ-UHFFFAOYSA-N 0.000 claims description 2
- OFPFYODEDAVXNF-UHFFFAOYSA-N 3-(difluoromethyl)-n-[2-(4,4-dimethylpentan-2-yl)phenyl]-1-methylpyrazole-4-carboxamide Chemical compound CC(C)(C)CC(C)C1=CC=CC=C1NC(=O)C1=CN(C)N=C1C(F)F OFPFYODEDAVXNF-UHFFFAOYSA-N 0.000 claims description 2
- YINRVYFMJRYHQS-YSURURNPSA-N 3-(difluoromethyl)-n-[2-[3-fluoro-4-[(e)-methoxyiminomethyl]phenyl]phenyl]-1-methylpyrazole-4-carboxamide Chemical compound C1=C(F)C(/C=N/OC)=CC=C1C1=CC=CC=C1NC(=O)C1=CN(C)N=C1C(F)F YINRVYFMJRYHQS-YSURURNPSA-N 0.000 claims description 2
- ZGRRUJYVXGOCKO-UHFFFAOYSA-N 3-(difluoromethyl)-n-[4-fluoro-2-(4-methylpentan-2-yl)phenyl]-1-methylpyrazole-4-carboxamide Chemical compound CC(C)CC(C)C1=CC(F)=CC=C1NC(=O)C1=CN(C)N=C1C(F)F ZGRRUJYVXGOCKO-UHFFFAOYSA-N 0.000 claims description 2
- KAUKOYNNWCIDEO-UHFFFAOYSA-N 4-(difluoromethyl)-2-methyl-n-[2-(2-trimethylsilylethyl)thiophen-3-yl]-1,3-thiazole-5-carboxamide Chemical compound S1C(C)=NC(C(F)F)=C1C(=O)NC1=C(CC[Si](C)(C)C)SC=C1 KAUKOYNNWCIDEO-UHFFFAOYSA-N 0.000 claims description 2
- WQMVTGCKCKMBSJ-UHFFFAOYSA-N 4-(difluoromethyl)-2-methyl-n-[2-[4-(trifluoromethyl)phenyl]phenyl]-1,3-thiazole-5-carboxamide Chemical compound S1C(C)=NC(C(F)F)=C1C(=O)NC1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 WQMVTGCKCKMBSJ-UHFFFAOYSA-N 0.000 claims description 2
- OIOYSPTZGQFWPR-UHFFFAOYSA-N 4-(difluoromethyl)-n-[2-(4-iodophenyl)phenyl]-2-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C)=NC(C(F)F)=C1C(=O)NC1=CC=CC=C1C1=CC=C(I)C=C1 OIOYSPTZGQFWPR-UHFFFAOYSA-N 0.000 claims description 2
- VJCAQEXOCSZRFR-UHFFFAOYSA-N 4-(difluoromethyl)-n-[2-[3-fluoro-4-(trifluoromethyl)phenyl]phenyl]-2-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C)=NC(C(F)F)=C1C(=O)NC1=CC=CC=C1C1=CC=C(C(F)(F)F)C(F)=C1 VJCAQEXOCSZRFR-UHFFFAOYSA-N 0.000 claims description 2
- XCAKAGIKDKEPNI-UHFFFAOYSA-N 5-chloro-1-methyl-n-[2-(4-methylpentan-2-yl)phenyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound CC(C)CC(C)C1=CC=CC=C1NC(=O)C1=C(Cl)N(C)N=C1C(F)(F)F XCAKAGIKDKEPNI-UHFFFAOYSA-N 0.000 claims description 2
- KFLBOWOXKLIDCJ-UHFFFAOYSA-N 5-chloro-n-[2-(4,4-dimethylpentan-2-yl)phenyl]-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound CC(C)(C)CC(C)C1=CC=CC=C1NC(=O)C1=C(Cl)N(C)N=C1C(F)(F)F KFLBOWOXKLIDCJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005816 Penthiopyrad Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- SOLFVXJETDYRNS-UHFFFAOYSA-N n-[2-(3,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethylpyrazole-4-carboxamide Chemical compound CC1=NN(C)C(F)=C1C(=O)NC1=CC=CC=C1CCC(C)(C)C SOLFVXJETDYRNS-UHFFFAOYSA-N 0.000 claims description 2
- USOYHKJIXXCBHH-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)phenyl]-5-fluoro-1,3-dimethylpyrazole-4-carboxamide Chemical compound CC1=NN(C)C(F)=C1C(=O)NC1=CC=CC=C1C1=CC=C(Cl)C(Cl)=C1 USOYHKJIXXCBHH-UHFFFAOYSA-N 0.000 claims description 2
- PDORXAFPTBEINT-UHFFFAOYSA-N n-[2-(4,4-dimethylpentan-2-yl)phenyl]-1,3-dimethylpyrazole-4-carboxamide Chemical compound CC(C)(C)CC(C)C1=CC=CC=C1NC(=O)C1=CN(C)N=C1C PDORXAFPTBEINT-UHFFFAOYSA-N 0.000 claims description 2
- AZFODUAPUZFYJX-UHFFFAOYSA-N n-[2-(4,4-dimethylpentan-2-yl)phenyl]-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound CC(C)(C)CC(C)C1=CC=CC=C1NC(=O)C1=CN(C)N=C1C(F)(F)F AZFODUAPUZFYJX-UHFFFAOYSA-N 0.000 claims description 2
- FLZOYGGRUBRZKQ-UHFFFAOYSA-N n-[2-(4,4-dimethylpentan-2-yl)phenyl]-5-fluoro-1,3-dimethylpyrazole-4-carboxamide Chemical compound CC(C)(C)CC(C)C1=CC=CC=C1NC(=O)C1=C(F)N(C)N=C1C FLZOYGGRUBRZKQ-UHFFFAOYSA-N 0.000 claims description 2
- LBWGCYNZIUGHGN-UHFFFAOYSA-N n-[2-(4,4-dimethylpentan-2-yl)phenyl]-5-fluoro-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound CC(C)(C)CC(C)C1=CC=CC=C1NC(=O)C1=C(F)N(C)N=C1C(F)(F)F LBWGCYNZIUGHGN-UHFFFAOYSA-N 0.000 claims description 2
- NOTMCFVPRDIUAV-UHFFFAOYSA-N n-[2-(4-bromophenyl)phenyl]-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C)=NC(C(F)F)=C1C(=O)NC1=CC=CC=C1C1=CC=C(Br)C=C1 NOTMCFVPRDIUAV-UHFFFAOYSA-N 0.000 claims description 2
- AYVPXJFRSYHRJX-UHFFFAOYSA-N n-[2-(4-chloro-3-fluorophenyl)phenyl]-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C)=NC(C(F)F)=C1C(=O)NC1=CC=CC=C1C1=CC=C(Cl)C(F)=C1 AYVPXJFRSYHRJX-UHFFFAOYSA-N 0.000 claims description 2
- YVXPNONPUCCDRY-UHFFFAOYSA-N n-[2-(4-chlorophenyl)phenyl]-3-iodo-1-methylpyrazole-4-carboxamide Chemical compound IC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(Cl)C=C1 YVXPNONPUCCDRY-UHFFFAOYSA-N 0.000 claims description 2
- ZBCYASQOTTWDIV-UHFFFAOYSA-N n-[2-(4-chlorophenyl)phenyl]-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C)=NC(C(F)F)=C1C(=O)NC1=CC=CC=C1C1=CC=C(Cl)C=C1 ZBCYASQOTTWDIV-UHFFFAOYSA-N 0.000 claims description 2
- UAOTVYDWYTYXJN-UHFFFAOYSA-N n-[2-[3-fluoro-4-(trifluoromethyl)phenyl]phenyl]-3-iodo-1-methylpyrazole-4-carboxamide Chemical compound IC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(C(F)(F)F)C(F)=C1 UAOTVYDWYTYXJN-UHFFFAOYSA-N 0.000 claims description 2
- 241000255925 Diptera Species 0.000 claims 1
- -1 ethylsulfinyl Chemical group 0.000 description 154
- 239000000460 chlorine Substances 0.000 description 124
- 229910052801 chlorine Inorganic materials 0.000 description 124
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 122
- 235000019000 fluorine Nutrition 0.000 description 120
- 239000011737 fluorine Substances 0.000 description 119
- 229910052731 fluorine Inorganic materials 0.000 description 119
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 118
- 239000001257 hydrogen Substances 0.000 description 109
- 229910052739 hydrogen Inorganic materials 0.000 description 109
- 150000002431 hydrogen Chemical class 0.000 description 97
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 93
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 74
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 73
- 229910052794 bromium Inorganic materials 0.000 description 73
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 71
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- 125000005843 halogen group Chemical group 0.000 description 41
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- 125000001424 substituent group Chemical group 0.000 description 28
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- 125000000623 heterocyclic group Chemical group 0.000 description 18
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- 229940074152 thuringiensin Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A 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-CSLFJTBJSA-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
- 238000009834 vaporization Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene 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
- 150000003751 zinc Chemical class 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
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
- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Aは、場合により置換されていてもよいアリール又は芳香族若しくは非芳香族の5員若しくは6員の炭素環式環若しくはヘテロ環式環(該ヘテロ環式環は、O、N又はSであり得る1から3個のヘテロ原子を有する)を表し(該炭素環又はヘテロ環は、アルキル、ハロゲン、ハロアルキル、アルキルチオ、アルキルスルフィニル及びアルキルスルホニルからなる群から選択される1、2又は3の置換基を有し得る);
R1は、水素、C1−C8−アルキル、C1−C6−アルキルスルフィニル、C1−C6−アルキルスルホニル、C1−C4−アルコキシ−C1−C4−アルキル若しくはC3−C8−シクロアルキル;いずれの場合も1から9個のフッ素、塩素及び/若しくは臭素原子を有するC1−C6−ハロアルキル、C1−C4−ハロアルキルチオ、C1−C4−ハロアルキルスルフィニル、C1−C4−ハロアルキルスルホニル、ハロ−C1−C4−アルコキシ−C1−C4−アルキル若しくはC3−C8−ハロシクロアルキル;ホルミル、ホルミル−C1−C3−アルキル、(C1−C3−アルキル)カルボニル−C1−C3−アルキル若しくは(C1−C3−アルコキシ)カルボニル−C1−C3−アルキル;いずれの場合も1から13個のフッ素、塩素及び/若しくは臭素原子を有するハロ−(C1−C3−アルキル)カルボニル−C1−C3−アルキル若しくはハロ−(C1−C3−アルコキシ)カルボニル−C1−C3−アルキル;(C1−C8−アルキル)カルボニル、(C1−C8−アルコキシ)カルボニル、(C1−C8−アルキルチオ)カルボニル、(C1−C4−アルコキシ−C1−C4−アルキル)カルボニル、(C3−C6−アルケニルオキシ)カルボニル、(C3−C6−アルキニルオキシ)カルボニル若しくは(C3−C8−シクロアルキル)カルボニル;いずれの場合も1から9個のフッ素、塩素及び/若しくは臭素原子を有する(C1−C6−ハロアルキル)カルボニル、(C1−C6−ハロアルコキシ)カルボニル、(C1−C6−ハロアルキルチオ)カルボニル、(ハロ−C1−C4−アルコキシ−C1−C4−アルキル)カルボニル、(C3−C6−ハロアルケニルオキシ)カルボニル、(C3−C6−ハロアルキニルオキシ)カルボニル若しくは(C3−C8−ハロシクロアルキル)カルボニル;−CH2−C≡C−R1−A、−CH2−CH=CH−R1−A、−CH=C=CH−R1−A、−C(=O)C(=O)R2、−CONR3R4若しくは−CH2NR5R6を表し;
R1−Aは、水素、C1−C6−アルキル、C1−C6−ハロアルキル、C2−C6−アルケニル、C2−C6−アルキニル、C3−C7−シクロアルキル、(C1−C4−アルコキシ)カルボニル、(C3−C6−アルケニルオキシ)カルボニル、(C3−C6−アルキニルオキシ)カルボニル又はシアノを表し;
R2は、水素、C1−C8−アルキル、C1−C8−アルコキシ、C1−C4−アルコキシ−C1−C4−アルキル若しくはC3−C8−シクロアルキル;いずれの場合も1から9個のフッ素、塩素及び/若しくは臭素原子を有するC1−C6−ハロアルキル、C1−C6−ハロアルコキシ、ハロ−C1−C4−アルコキシ−C1−C4−アルキル若しくはC3−C8−ハロシクロアルキルを表し;
R3及びR4は、互いに独立して、それぞれ、水素、C1−C8−アルキル、C1−C4−アルコキシ−C1−C4−アルキル若しくはC3−C8−シクロアルキル;いずれの場合も1から9個のフッ素、塩素及び/若しくは臭素原子を有するC1−C8−ハロアルキル、ハロ−C1−C4−アルコキシ−C1−C4−アルキル若しくはC3−C8−ハロシクロアルキルを表し;
R3とR4は、さらにまた、それらが結合している窒素原子と一緒になって、飽和ヘテロ環(該飽和ヘテロ環は、ハロゲン及びC1−C4−アルキルからなる群からの同一であるか又は異なっている置換基で場合により1置換又は多置換されていてもよく、また、該飽和ヘテロ環は、5から8個の環原子を有し、その際、該ヘテロ環は、酸素、硫黄及びNR7からなる群からの1個又は2個の非隣接のさらなるヘテロ原子を含み得る)を形成し;
R5及びR6は、互いに独立して、水素、C1−C8−アルキル若しくはC3−C8−シクロアルキル;いずれの場合も1から9個のフッ素、塩素及び/若しくは臭素原子を有するC1−C8−ハロアルキル若しくはC3−C8−ハロシクロアルキルを表し;
R5とR6は、さらにまた、それらが結合している窒素原子と一緒になって、飽和ヘテロ環(該飽和ヘテロ環は、ハロゲン及びC1−C4−アルキルからなる群からの同一であるか又は異なっている置換基で場合により1置換又は多置換されていてもよく、また、該飽和ヘテロ環は、5から8個の環原子を有し、その際、該ヘテロ環は、酸素、硫黄及びNR7からなる群からの1個又は2個の非隣接のさらなるヘテロ原子を含み得る)を表し;
R7は、水素又はC1−C6−アルキルを表し;
Mは、フェニル環若しくはチオフェン環(これらは、それぞれ、R8で1置換されている)を表すか、又は、置換C3−C6−シクロアルキル若しくはC3−C6−シクロアルケニル(これらは、それぞれ、R8−Bで1置換から4置換されている)を表し;
R8は、水素、フッ素、塩素、メチル、イソプロピル、メチルチオ又はトリフルオロメチルを表し;
R8−Bは、水素、フッ素、塩素、C1−C4−アルキル又はC1−C4−ハロアルキルを表し;
Qは、直接結合、C1−C4−アルキレン、C2−C4−アルケニレン、O、S、SO、SO2又はNR9を表し;
R9は、水素、C1−C8−アルキル、C1−C4−アルコキシ−C1−C4−アルキル、C1−C4−アルキルチオ−C1−C4−アルキル、C2−C8−アルケニル、C2−C8−アルキニル、C1−C6−ハロアルキル、C2−C6−ハロアルケニル、C2−C6−ハロアルキニル又はC3−C6−シクロアルキルを表し;
Rは、いずれの場合も場合により置換されていてもよいフェニル、シクロアルキル若しくはビシクロアルキルを表すか、又は、非置換C2−C20−アルキルを表すか、又は、場合により置換されていてもよいC1−C20−アルキルを表す]
のカルボキサミド類を用いることができるということが見いだされた。
R12は、水素、シアノ、ハロゲン、ニトロ、C1−C4−アルキル、C1−C4−アルコキシ、C1−C4−アルキルチオ若しくはC3−C6−シクロアルキルを表すか、又は、いずれの場合も1から5個のハロゲン原子を有するC1−C4−ハロアルキル、C1−C4−ハロアルコキシ若しくはC1−C4−ハロアルキルチオを表すか、又は、アミノカルボニル若しくはアミノカルボニル−C1−C4−アルキルを表し;
R13は、水素、ハロゲン、シアノ、C1−C4−アルキル、C1−C4−アルコキシ又はC1−C4−アルキルチオを表し;
R14は、水素、C1−C4−アルキル、ヒドロキシ−C1−C4−アルキル、C2−C6−アルケニル、C3−C6−シクロアルキル、C1−C4−アルキルチオ−C1−C4−アルキル若しくはC1−C4−アルコキシ−C1−C4−アルキルを表すか、又は、いずれの場合も1から5個のハロゲン原子を有するC1−C4−ハロアルキル、C1−C4−ハロアルキルチオ−C1−C4−アルキル若しくはC1−C4−ハロアルコキシ−C1−C4−アルキルを表すか、又は、フェニルを表し;
R15及びR16は、互いに独立して、水素、ハロゲン、C1−C4−アルキル又は1から5個のハロゲン原子を有するC1−C4−ハロアルキルを表し;
R17は、ハロゲン、シアノ若しくはC1−C4−アルキルを表すか、又は、いずれの場合も1から5個のハロゲン原子を有するC1−C4−ハロアルキル若しくはC1−C4−ハロアルコキシを表し;
R18及びR19は、互いに独立して、水素、ハロゲン、C1−C4−アルキル又は1から5個のハロゲン原子を有するC1−C4−ハロアルキルを表し;
R20は、水素、ハロゲン、C1−C4−アルキル又は1から5個のハロゲン原子を有するC1−C4−ハロアルキルを表し;
R21は、水素、ハロゲン、ヒドロキシル、シアノ若しくはC1−C6−アルキルを表すか、又は、いずれの場合も1から5個のハロゲン原子を有するC1−C4−ハロアルキル、C1−C4−ハロアルコキシ若しくはC1−C4−ハロアルキルチオを表し;
R22は、ハロゲン、ヒドロキシル、シアノ、C1−C4−アルキル、C1−C4−アルコキシ若しくはC1−C4−アルキルチオを表すか、又は、いずれの場合も1から5個のハロゲン原子を有するC1−C4−ハロアルキル、C1−C4−ハロアルキルチオ若しくはC1−C4−ハロアルコキシを表し;
R23は、水素、ハロゲン、シアノ、C1−C4−アルキル、C1−C4−アルコキシ若しくはC1−C4−アルキルチオを表すか、又は、いずれの場合も1から5個のハロゲン原子を有するC1−C4−ハロアルキル若しくはC1−C4−ハロアルコキシを表すか、又は、C1−C4−アルキルスルフィニル若しくはC1−C4−アルキルスルホニルを表し;
R24は、C1−C4−アルキル又は1から5個のハロゲン原子を有するC1−C4−ハロアルキルを表し;
R25は、C1−C4−アルキルを表し;
Q1は、S(硫黄)、SO、SO2又はCH2を表し;
pは、0、1又は2を表し、そこで、pが2を表す場合は、R25が同一であるか又は異なった基を表し;
R26は、C1−C4−アルキル又は1から5個のハロゲン原子を有するC1−C4−ハロアルキルを表し;
R27は、C1−C4−アルキル又は1から5個のハロゲン原子を有するC1−C4−ハロアルキルを表し;
R28及びR29は、互いに独立して、水素、ハロゲン、アミノ、C1−C4−アルキル又は1から5個のハロゲン原子を有するC1−C4−ハロアルキルを表し;
R30は、水素、ハロゲン、C1−C4−アルキル又は1から5個のハロゲン原子を有するC1−C4−ハロアルキルを表し;
R31及びR32は、互いに独立して、水素、ハロゲン、アミノ、ニトロ、C1−C4−アルキル又は1から5個のハロゲン原子を有するC1−C4−ハロアルキルを表し;
R33は、水素、ハロゲン、C1−C4−アルキル又は1から5個のハロゲン原子を有するC1−C4−ハロアルキルを表し;
R34は、水素、ハロゲン、アミノ、C1−C4−アルキルアミノ、ジ(C1−C4−アルキル)アミノ、シアノ、C1−C4−アルキル又は1から5個のハロゲン原子を有するC1−C4−ハロアルキルを表し;
R35は、ハロゲン、C1−C4−アルキル又は1から5個のハロゲン原子を有するC1−C4−ハロアルキルを表し;
R36は、水素、ハロゲン、アミノ、C1−C4−アルキルアミノ、ジ(C1−C4−アルキル)アミノ、シアノ、C1−C4−アルキル又は1から5個のハロゲン原子を有するC1−C4−ハロアルキルを表し;
R37は、ハロゲン、C1−C4−アルキル又は1から5個のハロゲン原子を有するC1−C4−ハロアルキルを表し;
R38は、ハロゲン、C1−C4−アルキル又は1から5個のハロゲン原子を有するC1−C4−ハロアルキルを表し;
R39は、水素又はC1−C4−アルキルを表し;
R40は、ハロゲン又はC1−C4−アルキルを表し;
R41は、C1−C4−アルキル又は1から5個のハロゲン原子を有するC1−C4−ハロアルキルを表し;
R42は、水素、ハロゲン、C1−C4−アルキル又は1から5個のハロゲン原子を有するC1−C4−ハロアルキルを表し;
R43は、ハロゲン、ヒドロキシル、C1−C4−アルキル、C1−C4−アルコキシ若しくはC1−C4−アルキルチオを表すか、又は、いずれの場合も1から5個のハロゲン原子を有するC1−C4−ハロアルキル、C1−C4−ハロアルキルチオ若しくはC1−C4−ハロアルコキシを表し;
R44は、水素、シアノ、C1−C4−アルキル、1から5個のハロゲン原子を有するC1−C4−ハロアルキル、C1−C4−アルコキシ−C1−C4−アルキル、ヒドロキシ−C1−C4−アルキル、C1−C4−アルキルスルホニル、ジ(C1−C4−アルキル)アミノスルホニル若しくはC1−C6−アルキルカルボニルを表すか、又は、いずれの場合も場合により置換されていてもよいフェニルスルホニル若しくはベンゾイルを表し;
R45は、水素、ハロゲン、C1−C4−アルキル又は1から5個のハロゲン原子を有するC1−C4−ハロアルキルを表し;
R46は、水素、ハロゲン、シアノ、C1−C4−アルキル又は1から5個のハロゲン原子を有するC1−C4−ハロアルキルを表し;
R47は、水素、ハロゲン、C1−C4−アルキル又は1から5個のハロゲン原子を有するC1−C4−ハロアルキルを表し;
R48は、C1−C4−アルキルを表す。
いずれの場合も1から8個の炭素原子を有していて、いずれの場合も直鎖若しくは分枝鎖であるアルキル、ヒドロキシアルキル、オキソアルキル、アルコキシ、アルコキシアルキル、アルキルチオアルキル、ジアルコキシアルキル、アルキルチオ、アルキルスルフィニル若しくはアルキルスルホニル;
いずれの場合も2から6個の炭素原子を有していて、いずれの場合も直鎖若しくは分枝鎖であるアルケニル若しくはアルケニルオキシ;
いずれの場合も1から6個の炭素原子及び同一であるか若しくは異なっている1から13個のハロゲン原子を有していて、いずれの場合も直鎖若しくは分枝鎖であるハロアルキル、ハロアルコキシ、ハロアルキルチオ、ハロアルキルスルフィニル若しくはハロアルキルスルホニル;
いずれの場合も2から6個の炭素原子及び同一であるか若しくは異なっている1から11個のハロゲン原子を有していて、いずれの場合も直鎖若しくは分枝鎖であるハロアルケニル若しくはハロアルケニルオキシ;
いずれの場合も直鎖若しくは分枝鎖であり、それぞれの炭化水素鎖内に1から6個の炭素原子を有するアルキルアミノ、ジアルキルアミノ、アルキルカルボニル、アルキルカルボニルオキシ、アルコキシカルボニル、アルキルアミノカルボニル、ジアルキルアミノカルボニル、アリールアルキルアミノカルボニル若しくはジアルキルアミノカルボニルオキシ、それぞれの炭化水素鎖内に2から6個の炭素原子を有するアルケニルカルボニル若しくはアルキニルカルボニルを表すか;又は
いずれの場合も3から6個の炭素原子を有するシクロアルキル若しくはシクロアルキルオキシを表すか;又は
いずれの場合も二重に結合している、3個若しくは4個の炭素原子を有するアルキレン、2個若しくは3個の炭素原子を有するオキシアルキレン、若しくは、1個若しくは2個の炭素原子を有するジオキシアルキレン(これら基は、それぞれ、フッ素、塩素、オキソ、メチル、トリフルオロメチル及びエチルからなる群からの同一であるか又は異なっている置換基で場合により1置換から4置換されていてもよい);
基−C(Q1)=N−Q2[ここで、
Q1は、水素、ヒドロキシル、1から4個の炭素原子を有するアルキル、1から4個の炭素原子及び同一であるか若しくは異なっている1から9個のハロゲン原子を有するハロアルキル、又は、1から6個の炭素原子を有するシクロアルキルを表し;及び、
Q2は、ヒドロキシル、アミノ、メチルアミノ、フェニル若しくはベンジルを表すか、又は、1から4個の炭素原子を有していて、いずれの場合もハロゲン−、シアノ−、ヒドロキシル−、アルコキシ−、アルキルチオ−、アルキルアミノ−、ジアルキルアミノ−若しくはフェニル−で場合により置換されていてもよいアルキル若しくはアルコキシを表すか、又は、いずれの場合も2から4個の炭素原子を有するアルケニルオキシ若しくはアルキニルオキシを表し;Q2は、さらにまた、以下のものを表す:フェニル、フェノキシ、フェニルチオ、ベンゾイル、ベンゾイルエテニル、シンナモイル若しくはヘテロシクリル、又は、いずれの場合もそれぞれのアルキル部分内に1から3個の炭素原子を有するフェニルアルキル、フェニルアルキルオキシ、フェニルアルキルチオ若しくはヘテロシクリルアルキル(これら基は、それぞれ、環状部分においてハロゲン及び/又は直鎖若しくは分枝鎖の1から4個の炭素原子を有するアルキル若しくはアルコキシで場合により1置換から3置換されていてもよい)]を表す。
Q1は、水素、メチル、エチル、トリフルオロメチル又はシクロプロピルを表し;及び
Q2は、ヒドロキシル、メトキシ、エトキシ、プロポキシ又はイソプロポキシを表す]
を表す。
(1) 式
(6) 式
(7) 式
(12) 式
(22) 式
(23) 式
(24) 式
(26) 式
(29) 式
(31) 式
(35) 式
(38) 式
(39) 式
アルタナリア斑点病(alternaria leaf spot)(Alternaria spec. atrans tenuissima)、炭疽病(Colletotrichum gloeosporoides dematium var. truncatum)、褐紋病(brown spot)(Septoria glycines)、紫斑病(cercospora leaf spot and blight)(Cercospora kikuchii)、コアネホラ葉枯病(choanephora leaf blight)(Choanephora infundibulifera trispora(syn.))、ダクツリオホラ斑点病(dactuliophora leaf spot)(Dactuliophora glycines)、べと病(Peronospora manshurica)、ドレクスレラ胴枯病(drechslera blight)(Drechslera glycini)、斑点病(frogeye leaf spot)(Cercospora sojina)、そばかす病(leptosphaerulina leaf spot)(Leptosphaerulina trifolii)、灰星病(phyllostica leaf spot)(Phyllosticta sojaecola)、うどんこ病(Microsphaera diffusa)、ピレノカエタ斑点病(pyrenochaeta leaf spot)(Pyrenochaeta glycines)、葉腐病(rhizoctonia aerial, foliage, and web blight)(Rhizoctonia solani)、さび病(Phakopsora pachyrhizi)、黒とう病(Sphaceloma glycines)、ステムフィリウム葉枯病(stemphylium leaf blight)(Stemphylium botryosum)、褐色輪紋病(Corynespora cassiicola)、黒根腐病(Calonectria crotalariae)、炭腐病(Macrophomina phaseolina)、赤かび病(fusarium blight or wilt, root rot, and pod and collar rot)(Fusarium oxysporum、Fusarium orthoceras、Fusarium semitectum、Fusarium equiseti)、ミコレプトジスクス根腐病(mycoleptodiscus root rot)(Mycoleptodiscus terrestris)、根腐病(neocosmospora)(Neocosmopspora vasinfecta)、黒点病(Diaporthe phaseolorum)、茎腐爛病(stem canker)(Diaporthe phaseolorum var. caulivora)、茎疫病(phytophthora rot)(Phytophthora megasperma)、落葉病(brown stem rot)(Phialophora gregata)、根茎腐敗病(pythium rot)(Pythium aphanidermatum、Pythium irregulare、Pythium debaryanum、Pythium myriotylum、Pythium ultimum)、リゾクトニア根腐病(rhizoctonia root rot, stem decay, and damping−off)(Rhizoctonia solani)、菌核病(sclerotinia stem decay)(Sclerotinia sclerotiorum)、スクレロチニアサウザンブライト病(sclerotinia southern blight)(Sclerotinia rolfsii)、チエラビオプシス根腐病(thielaviopsis root rot)(Thielaviopsis basicola)。特に好ましくは、ファコプソラ・パキリジ(Phakopsora pachyrhizi)を防除するために式(I)のカルボキサミド類を使用する。
2−フェニルフェノール;8−ヒドロキシキノリンスルフェート;アシベンゾラル−S−メチル;アルジモルフ;アミドフルメト;アンプロピルホス;アンプロピルホス−カリウム;アンドプリム;アニラジン;アザコナゾール;アゾキシストロビン;ベナラキシル;ベノダニル;ベノミル;ベンチアバリカルブ−イソプロピル;ベンザマクリル;ベンザマクリル−イソブチル;ビラナホス;ビナパクリル;ビフェニル;ビテルタノール;ブラストサイジン−S;ボスカリド;ブロムコナゾール;ブピリメート;ブチオベート;ブチルアミン;多硫化カルシウム;カプシマイシン(capsimycin);キャプタホール;キャプタン;カルベンダジム;カルボキシン;カルプロパミド;カルボン;キノメチオネート;クロベンチアゾン;クロルフェナゾール;クロロネブ;クロロタロニル;クロゾリネート;クロジラコン;シアゾファミド;シフルフェナミド;シモキサニル;シプロコナゾール;シプロジニル;シプロフラム;Dagger G;デバカルブ;ジクロフルアニド;ジクロン;ジクロロフェン;ジクロシメット;ジクロメジン;ジクロラン;ジエトフェンカルブ;ジフェノコナゾール;ジフルメトリム;ジメチリモール;ジメトモルフ;ジモキシストロビン;ジニコナゾール;ジニコナゾール−M;ジノカップ;ジフェニルアミン;ジピリチオン;ジタリムホス;ジチアノン;ドジン;ドラゾクソロン;エジフェンホス;エポキシコナゾール;エタボキサム;エチリモール;エトリジアゾール;ファモキサドン;フェンアミドン;フェナパニル;フェナリモール;フェンブコナゾール;フェンフラム;フェンヘキサミド;フェニトロパン;フェノキサニル;フェンピクロニル;フェンプロピジン;フェンプロピモルフ;ファーバム;フルアジナム;フルベンジミン;フルジオキソニル;フルメトベル(flumetover);フルモルフ;フルオロイミド(fluoromide);フルオキサストロビン;フルキンコナゾール;フルルプリミドール;フルシラゾール;フルスルファミド;フルトラニル;フルトリアホール;ホルペット;ホセチル−Al;ホセチル−ナトリウム;フベリダゾール;フララキシル;フラメトピル;フルカルバニル;フルメシクロックス;グアザチン;ヘキサクロロベンゼン;ヘキサコナゾール;ヒメキサゾール;イマザリル;イミベンコナゾール;イミノクタジン三酢酸塩;イミノクタジントリス(アルベシル酸塩);ヨードカルブ;イプコナゾール;イプロベンホス;イプロジオン;イプロバリカルブ;イルママイシン;イソプロチオラン;イソバレジオン;カスガマイシン;クレソキシム−メチル;マンゼブ;マンネブ;メフェリムゾン;メパニピリム;メプロニル;メタラキシル;メタラキシル−M;メトコナゾール;メタスルホカルブ;メトフロキサム;メチラム;メトミノストロビン;メトスルフォバックス;ミルディオマイシン;ミクロブタニル;ミクロゾリン;ナタマイシン;ニコビフェン;ニトロタル−イソプロピル;ノビフルムロン;ヌアリモール;オフラセ;オリサストロビン;オキサジキシル;オキソリン酸;オキシポコナゾール;オキシカルボキシン;オキシフェンチイン(oxyfenthiin);パクロブトラゾール;ペフラゾエート;ペンコナゾール;ペンシクロン;ホスダイフェン;フタリド;ピコキシストロビン;ピペラリン;ポリオキシン;ポリオキソリム;プロベナゾール;プロクロラズ;プロシミドン;プロパモカルブ;プロパノシン−ナトリウム(propanosine−sodium);プロピコナゾール;プロピネブ;プロキナジド;プロチオコナゾール;ピラクロストロビン;ピラゾホス;ピリフェノックス;ピリメタニル;ピロキロン;ピロキシフル;ピロルニトリン;キンコナゾール;キノキシフェン;キントゼン;シメコナゾール;スピロキサミン;硫黄;テブコナゾール;テクロフタラム;テクナゼン;テトシクラシス;テトラコナゾール;チアベンダゾール;チシオフェン;チフルザミド;チオファネート−メチル;チウラム;チオキシミド;トルクロホス−メチル;トリルフルアニド;トリアジメホン;トリアジメノール;トリアズブチル;トリアゾキシド;トリシクラミド;トリシクラゾール;トリデモルフ;トリフロキシストロビン;トリフルミゾール;トリホリン;トリチコナゾール;ウニコナゾール;バリダマイシンA;ビンクロゾリン;ジネブ;ジラム;ゾキサミド;(2S)−N−[2−[4−[[3−(4−クロロフェニル)−2−プロピニル]オキシ]−3−メトキシフェニル]エチル]−3−メチル−2−[(メチルスルホニル)アミノ]ブタンアミド;1−(1−ナフタレニル)−1H−ピロール−2,5−ジオン;2,3,5,6−テトラクロロ−4−(メチルスルホニル)ピリジン;2−アミノ−4−メチル−N−フェニル−5−チアゾールカルボキサミド;2−クロロ−N−(2,3−ジヒドロ−1,1,3−トリメチル−1H−インデン−4−イル)−3−ピリジンカルボキサミド;3,4,5−トリクロロ−2,6−ピリジンジカルボニトリル;アクチノベート(actinovate);シス−1−(4−クロロフェニル)−2−(1H−1,2,4−トリアゾール−1−イル)シクロヘプタノール;1−(2,3−ジヒドロ−2,2−ジメチル−1H−インデン−1−イル)−1H−イミダゾール−5−カルボン酸メチル;炭酸一カリウム(monopotassium carbonate);N−(6−メトキシ−3−ピリジニル)シクロプロパンカルボキサミド;N−ブチル−8−(1,1−ジメチルエチル)−1−オキサスピロ[4.5]デカン−3−アミン;四チオ炭酸ナトリウム(sodium tetrathiocarbonate);並びに、銅塩及び銅調製物、例えば、ボルドー液;水酸化銅;ナフテン酸銅;塩基性塩化銅;硫酸銅;クフラネブ;酸化銅;マンカッパー;オキシン銅。
ブロノポール、ジクロロフェン、ニトラピリン、ジメチルジチオカルバミン酸ニッケル、カスガマイシン、オクチリノン、フランカルボン酸、オキシテトラサイクリン、プロベナゾール、ストレプトマイシン、テクロフタラム、硫酸銅及び別の銅剤。
1. アセチルコリンエステラーゼ(AChE)阻害薬
1.1 カーバメート系(例えば、アラニカルブ、アルジカルブ、アルドキシカルブ、アリキシカルブ、アミノカルブ、アザメチホス、ベンジオカルブ、ベンフラカルブ、ブフェンカルブ、ブタカルブ、ブトカルボキシム、ブトキシカルボキシム、カルバリル、カルボフラン、カルボスルファン、クロエトカルブ、クマホス、シアノフェンホス、シアノホス、ジメチラン、エチオフェンカルブ、フェノブカルブ、フェノチオカルブ、ホルメタネート、フラチオカルブ、イソプロカルブ、メタム−ナトリウム、メチオカルブ、メソミル、メトルカルブ、オキサミル、ピリミカーブ、プロメカルブ、プロポクスル、チオジカルブ、チオファノックス、トリアザメート、トリメタカルブ、XMC、キシリルカルブ);
1.2 有機リン酸エステル系(例えば、アセフェート、アザメチホス、アジンホス(−メチル,−エチル)、ブロモホス−エチル、ブロムフェンビンホス(−メチル)、ブタチオホス、カズサホス、カルボフェノチオン、クロルエトキシホス、クロルフェンビンホス、クロルメホス、クロルピリホス(−メチル/−エチル)、クマホス、シアノフェンホス、シアノホス、クロルフェンビンホス、ジメトン−S−メチル、ジメトン−S−メチルスルホン、ジアリホス、ダイアジノン、ジクロフェンチオン、ジクロルボス/DDVP、ジクロトホス、ジメトエート、ジメチルビンホス、ジオキサベンゾホス、ダイスルホトン、EPN、エチオン、エトプロホス、エトリムホス、ファムフール、フェナミホス、フェニトロチオン、フェンスルホチオン、フェンチオン、フルピラゾホス、ホノホス、ホルモチオン、ホスメチラン、ホスチアゼート、ヘプテノホス、ヨードフェンホス、イプロベンホス、イサゾホス、イソフェンホス、O−サリチル酸イソプロピル、イソキサチオン、マラチオン、メカルバム、メタクリホス、メタミドホス、メチダチオン、メビンホス、モノクロトホス、ナレド、オメトエート、オキシジメトン−メチル、パラチオン(−メチル/−エチル)、フェントエート、ホレート、ホサロン、ホスメット、ホスファミドン、ホスホカルブ、ホキシム、ピリミホス(−メチル/−エチル)、プロフェノホス、プロパホス、プロペタムホス、プロチオホス、プロトエート、ピラクロホス、ピリダフェンチオン、ピリダチオン(pyridathion)、キナルホス、セブホス(sebufos)、スルホテップ、スルプロホス、テブピリムホス、テメホス、テルブホス、テトラクロロビンホス、チオメトン、トリアゾホス、トリクロルホン、バミドチオン);
2. ナトリウムチャンネルモジュレーター/電位依存性ナトリウムチャンネル遮断薬
2.1 ピレスロイド系(例えば、アクリナトリン、アレスリン(d−シス−トランス,d−トランス)、ベータ−シフルトリン、ビフェントリン、ビオアレスリン、ビオアレスリン−S−シクロペンチル異性体、ビオエタノメトリン(bioethanomethrin)、ビオペルメトリン、ビオレスメトリン、クロバポルトリン(chlovaporthrin)、シス−シペルメトリン、シス−レスメトリン、シス−ペルメトリン、クロシトリン(clocythrin)、シクロプロトリン、シフルトリン、シハロトリン、シペルメトリン(アルファ−,ベータ−,シータ−,ゼータ−)、シフェノトリン、DDT、デルタメトリン、エムペントリン(1R異性体)、エスフェンバレレート、エトフェンプロックス、フェンフルトリン(fenfluthrin)、フェンプロパトリン、フェンピリトリン、フェンバレレート、フルブロシトリネート(flubrocythrinate)、フルシトリネート、フルフェンプロックス、フルメトリン、フルバリネート、フブフェンプロックス(fubfenprox)、ガンマ−シハロトリン、イミプロトリン、カデトリン、ラムダ−シハロトリン、メトフルトリン、ペルメトリン(シス−,トランス−)、フェノトリン(1Rトランス異性体)、プラレトリン、プロフルトリン、プロトリフェンブト(protrifenbute)、ピレスメトリン、レスメトリン、RU 15525、シラフルオフェン、タウ−フルバリネート、テフルトリン、テラレトリン、テトラメトリン(1R異性体)、トラロメトリン、トランスフルトリン、ZXI 8901、ピレトリン類(除虫菊(pyrethrum)));
2.2 オキサジアジン系(例えば、インドキサカルブ);
3. アセチルコリン受容体作動薬/拮抗薬
3.1 クロロニコチニル系/ネオニコチノイド系(例えば、アセタミプリド、クロチアニジン、ジノテフラン、イミダクロプリド、ニテンピラム、ニチアジン、チアクロプリド、チアメトキサム);
3.2 ニコチン、ベンスルタップ、カルタップ;
4. アセチルコリン受容体モジュレーター
4.1 スピノシン系(例えば、スピノサド);
5. GABA制御塩化物チャンネル拮抗薬
5.1 シクロジエン有機塩素系(例えば、カンフェクロル、クロルダン、エンドスルファン、ガンマ−HCH、HCH、ヘプタクロル、リンダン、メトキシクロル);
5.2 フィプロール系(例えば、アセトプロール、エチプロール、フィプロニル、バニリプロール(vaniliprole));
6. 塩化物チャンネル活性化剤
6.1 メクチン系(例えば、アバメクチン、アベルメクチン、エマメクチン、エマメクチン安息香酸塩、イベルメクチン、ミルベメクチン、ミルベマイシン);
7. 幼若ホルモンミメティクス
(例えば、ジオフェノラン、エポフェノナン、フェノキシカルブ、ハイドロプレン、キノプレン、メトプレン、ピリプロキシフェン、トリプレン(triprene));
8. エクジソン作動薬/ディスラプター
8.1 ジアシルヒドラジン系(例えば、クロマフェノジド、ハロフェノジド、メトキシフェノジド、テブフェノジド);
9. キチン生合成阻害薬
9.1 ベンゾイル尿素系(例えば、ビストリフルロン、クロルフルアズロン(chlofluazuron)、ジフルベンズロン、フルアズロン、フルシクロクスロン、フルフェノクスロン、ヘキサフルムロン、ルフェヌロン、ノバルロン、ノビフルムロン、ペンフルロン(penfluron)、テフルベンズロン、トリフルムロン);
9.2 ブプロフェジン;
9.3 シロマジン;
10. 酸化的リン酸化阻害薬、ATPディスラプター
10.1 ジアフェンチウロン;
10.2 有機スズ系(例えば、アゾシクロチン、シヘキサチン、酸化フェンブタスズ);
11. H−プロトン勾配を遮断することによる酸化的リン酸化の脱共役剤
11.1 ピロール系(例えば、クロルフェナピル);
11.2 ジニトロフェノール系(例えば、ビナパクリル、ジノブトン、ジノカップ、DNOC);
12. Site−I 電子伝達阻害薬
12.1 METI系(例えば、フェナザキン、フェンピロキシメート、ピリミジフェン、ピリダベン、テブフェンピラド、トルフェンピラド);
12.2 ヒドラメチルノン;
12.3 ジコホル;
13. Site−II 電子伝達阻害薬
13.1 ロテノン;
14. Site−III 電子伝達阻害薬
14.1 アセキノシル、フルアクリピリム;
15. 昆虫消化管膜の微生物ディスラプター
バシルス・ツリンギエンシス(Bacillus thuringiensis)株
16. 脂肪合成阻害薬
16.1 テトロン酸系(例えば、スピロジクロフェン、スピロメシフェン);
16.2 テトラミン酸系[例えば、3−(2,5−ジメチルフェニル)−8−メトキシ−2−オキソ−1−アザスピロ[4.5]デク−3−エン−4−イルエチルカルボナート(別名:炭酸3−(2,5−ジメチルフェニル)−8−メトキシ−2−オキソ−1−アザスピロ[4.5]デク−3−エン−4−イルエチルエステル、CAS Reg.No.382608−10−8)、及び、炭酸シス−3−(2,5−ジメチルフェニル)−8−メトキシ−2−オキソ−1−アザスピロ[4.5]デク−3−エン−4−イルエチルエステル(CAS Reg.No.203313−25−1)];
17. カルボキサミド系
(例えば、フロニカミド);
18. オクトパミン作用薬
(例えば、アミトラズ);
19. マグネシウム刺激ATPアーゼの阻害薬
(例えば、プロパルギット);
20. フタルアミド系
(例えば、N2−[1,1−ジメチル−2−(メチルスルホニル)エチル]−3−ヨード−N1−[2−メチル−4−[1,2,2,2−テトラフルオロ−1−(トリフルオロメチル)エチル]フェニル]−1,2−ベンゼンジカルボキサミド(CAS−Reg.No.:272451−65−7));
21. ネライストキシン類似体
(例えば、チオシクラムシュウ酸水素塩(thiocyclam hydrogen oxalate)、チオスルタップ−ナトリウム(thiosultap−sodium));
22. 生物学的薬剤、ホルモン又はフェロモン
(例えば、アザジラクチン、バシルス属種(Bacillus spec.)、ベアウベリア属種(Beauveria spec.)、コドレモン(codlemone)、メタリジウム属種(Metarrhizium spec.)、パエシロマイセス属種(Paecilomyces spec.)、チューリンギエンシン(thuringiensin)、ベルチシリウム属種(Verticillium spec.));
23. 作用機序が知られていないか又は特定されていない活性化合物
23.1 燻蒸剤(例えば、リン化アルミニウム、臭化メチル、フッ化スルフリル);
23.2 選択的摂食阻害薬(例えば、氷晶石(cryolite)、フロニカミド、ピメトロジン);
23.3 ダニ成長阻害薬(例えば、クロフェンテジン、エトキサゾール、ヘキシチアゾクス);
23.4 アミドフルメト、ベンクロチアズ、ベンゾキシメート、ビフェナゼート、ブロモプロピレート、ブプロフェジン、キノメチオネート、クロルジメホルム、クロロベンジレート、クロロピクリン、クロチアゾベン(clothiazoben)、シクロプレン(cycloprene)、ジシクラニル、フェノキサクリム、フェントリファニル(fentrifanil)、フルベンジミン、フルフェネリム、フルテンジン(flutenzin)、ゴシプルレ(gossyplure)、ヒドラメチルノン、ジャポニルレ(japonilure)、メトキサジアゾン、石油、ピペロニルブトキシド、オレイン酸カリウム、ピリダリル、スルフルラミド、テトラジホン、テトラスル、トリアラセン、ベルブチン(verbutin);
さらに、化合物プロピルカルバミン酸3−メチルフェニル(ツマサイドZ)、化合物3−(5−クロロ−3−ピリジニル)−8−(2,2,2−トリフルオロエチル)−8−アザビシクロ[3.2.1]オクタン−3−カルボニトリル(CAS Reg.No.185982−80−3)及び対応する3−エンド異性体(CAS Reg.No.185984−60−5)(cf. WO 96/37494、WO 98/25923);
並びに、殺虫活性を有する植物抽出物、線虫類、菌類又はウイルス類を含んでいる調製物。
実施例A
大豆さび病防除試験/散布施用
5重量部の式(I)のカルボキサミド、142.4重量部のアセトン及び7.5重量部の乳化剤(ポリオキシエチレンアルキルフェニルエーテル)を混合させ、水を用いて所望の濃度に調製した。
直径7.5cmのプラスチック製容器内で、ダイズ(品種:Enrei)を栽培した。いずれの場合も3つの容器内で、2.3葉期に達した実生に、6mLの被験物質(上記調製物)を散布した。散布の1日後、その葉に、ファコプソラ・パキリジ(Phakopsora pachyrhizi)の夏胞子懸濁液(1×105夏胞子/mL)を用いて接種した。その接種をしてから14日後、各容器について、感染の程度を評価し、効力を計算した。薬害についても、モニターした。
Claims (4)
- ファコプソラ・パキリジ(Phakopsora pachyrhizi)を防除するための、
(1) N−[2−(1,3−ジメチルブチル)フェニル]−1,3−ジメチル−1H−ピラゾール−4−カルボキサミド;
(2) N−[2−(1,3−ジメチルブチル)フェニル]−5−フルオロ−1,3−ジメチル−1H−ピラゾール−4−カルボキサミド;
(3) N−[2−(1,3−ジメチルブチル)フェニル]−5−クロロ−1,3−ジメチル−1H−ピラゾール−4−カルボキサミド;
(4) 3−(ジフルオロメチル)−N−[2−(1,3−ジメチルブチル)フェニル]−1−メチル−1H−ピラゾール−4−カルボキサミド;
(5) 3−(トリフルオロメチル)−N−[2−(1,3−ジメチルブチル)フェニル]−5−フルオロ−1−メチル−1H−ピラゾール−4−カルボキサミド;
(6) 3−(トリフルオロメチル)−N−[2−(1,3−ジメチルブチル)フェニル]−5−クロロ−1−メチル−1H−ピラゾール−4−カルボキサミド;
(7) 1,3−ジメチル−N−[2−(1,3,3−トリメチルブチル)フェニル]−1H−ピラゾール−4−カルボキサミド;
(8) 5−フルオロ−1,3−ジメチル−N−[2−(1,3,3−トリメチルブチル)フェニル]−1H−ピラゾール−4−カルボキサミド;
(9) 3−(ジフルオロメチル)−1−メチル−N−[2−(1,3,3−トリメチルブチル)フェニル]−1H−ピラゾール−4−カルボキサミド;
(10) 3−(トリフルオロメチル)−1−メチル−N−[2−(1,3,3−トリメチルブチル)フェニル]−1H−ピラゾール−4−カルボキサミド;
(11) 3−(トリフルオロメチル)−5−フルオロ−1−メチル−N−[2−(1,3,3−トリメチルブチル)フェニル]−1H−ピラゾール−4−カルボキサミド;
(12) 3−(トリフルオロメチル)−5−クロロ−1−メチル−N−[2−(1,3,3−トリメチルブチル)フェニル]−1H−ピラゾール−4−カルボキサミド;
(18) N−(3−p−トリルチオフェン−2−イル)−1−メチル−3−トリフルオロメチル−1H−ピラゾール−4−カルボキサミド;
(19) ペンチオピラド;
(21) N−(3’,4’−ジクロロ−5−フルオロ−1,1’−ビフェニル−2−イル)−3−(ジフルオロメチル)−1−メチル−1H−ピラゾール−4−カルボキサミド;
(22) 3−(ジフルオロメチル)−N−{3’−フルオロ−4’−[(E)−(メトキシイミノ)メチル]−1,1’−ビフェニル−2−イル}−1−メチル−1H−ピラゾール−4−カルボキサミド;
(23) 3−(トリフルオロメチル)−N−{3’−フルオロ−4’−[(E)−(メトキシイミノ)メチル]−1,1’−ビフェニル−2−イル}−1−メチル−1H−ピラゾール−4−カルボキサミド;
(24) N−(3’,4’−ジクロロ−1,1’−ビフェニル−2−イル)−5−フルオロ−1,3−ジメチル−1H−ピラゾール−4−カルボキサミド;
(25) N−(4’−クロロ−3’−フルオロ−1,1’−ビフェニル−2−イル)−2−メチル−4−(トリフルオロメチル)−1,3−チアゾール−5−カルボキサミド;
(26) N−(4’−クロロ−1,1’−ビフェニル−2−イル)−4−(ジフルオロメチル)−2−メチル−1,3−チアゾール−5−カルボキサミド;
(27) N−(4’−ブロモ−1,1’−ビフェニル−2−イル)−4−(ジフルオロメチル)−2−メチル−1,3−チアゾール−5−カルボキサミド;
(28) 4−(ジフルオロメチル)−2−メチル−N−[4’−(トリフルオロメチル)−1,1’−ビフェニル−2−イル]−1,3−チアゾール−5−カルボキサミド;
(29) N−(4’−ヨード−1,1’−ビフェニル−2−イル)−4−(ジフルオロメチル)−2−メチル−1,3−チアゾール−5−カルボキサミド;
(30) N−(4’−クロロ−3’−フルオロ−1,1’−ビフェニル−2−イル)−2−メチル−4−(ジフルオロメチル)−1,3−チアゾール−5−カルボキサミド;
(32) N−[2−(1,3−ジメチルブチル)フェニル]−1−メチル−4−(トリフルオロメチル)−1H−ピロール−3−カルボキサミド;
(33) N−(4’−クロロビフェニル−2−イル)−3−ヨード−1−メチル−1H−ピラゾール−4−カルボキサミド;
(34) 4−(ジフルオロメチル)−N−[3’−フルオロ−4’−(トリフルオロメチル)ビフェニル−2−イル]−2−メチル−1,3−チアゾール−5−カルボキサミド;
(35) 3−(ジフルオロメチル)−N−[2−(3,3−ジメチルブチル)フェニル]−1−メチル−1H−ピラゾール−4−カルボキサミド;
(36) N−[2−(3,3−ジメチルブチル)フェニル]−5−フルオロ−1,3−ジメチル−1H−ピラゾール−4−カルボキサミド;
(37) N−[3’−フルオロ−4’−(トリフルオロメチル)ビフェニル−2−イル]−3−ヨード−1−メチル−1H−ピラゾール−4−カルボキサミド;
(38) 3−(ジフルオロメチル)−N−[2−(1,3−ジメチルブチル)−4−フルオロフェニル]−1−メチル−1H−ピラゾール−4−カルボキサミド;
(39) 4−(ジフルオロメチル)−2−メチル−N−{2−[2−(トリメチルシリル)エチル]−3−チエニル}−1,3−チアゾール−5−カルボキサミド;
からなる群から選択されるカルボキサミド類の使用。 - ファコプソラ・パキリジ(Phakopsora pachyrhizi)を防除するための、
(2) N−[2−(1,3−ジメチルブチル)フェニル]−5−フルオロ−1,3−ジメチル−1H−ピラゾール−4−カルボキサミド;及び
(21) N−(3’,4’−ジクロロ−5−フルオロ−1,1’−ビフェニル−2−イル)−3−(ジフルオロメチル)−1−メチル−1H−ピラゾール−4−カルボキサミド;
からなる群から選択される、請求項1に記載のカルボキサミド類の使用。 - ダイズ植物中のファコプソラ・パキリジ(Phakopsora pachyrhizi)を防除する方法であって、該ダイズ植物を請求項1又は2に記載のカルボキサミド類で処理することを特徴とする、前記方法。
- トランスジェニックダイズ植物の病害を防除するための、請求項3に記載の方法。
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DE102005025989A DE102005025989A1 (de) | 2005-06-07 | 2005-06-07 | Carboxamide |
DE102005025989.8 | 2005-06-07 | ||
PCT/EP2006/005070 WO2006131221A2 (de) | 2005-06-07 | 2006-05-26 | Carboxamide |
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-
2005
- 2005-06-07 DE DE102005025989A patent/DE102005025989A1/de not_active Withdrawn
-
2006
- 2006-05-26 KR KR1020077030454A patent/KR20080018912A/ko not_active Application Discontinuation
- 2006-05-26 WO PCT/EP2006/005070 patent/WO2006131221A2/de active Application Filing
- 2006-05-26 CN CN2006800203758A patent/CN101212899B/zh not_active Expired - Fee Related
- 2006-05-26 US US11/916,436 patent/US8431600B2/en active Active
- 2006-05-26 BR BRPI0613488A patent/BRPI0613488B1/pt active IP Right Grant
- 2006-05-26 EP EP06743073A patent/EP1890540A2/de not_active Withdrawn
- 2006-05-26 JP JP2008515089A patent/JP5069679B2/ja not_active Expired - Fee Related
- 2006-06-05 AR AR20060102336A patent/AR054280A1/es unknown
- 2006-06-06 TW TW095119939A patent/TW200715967A/zh unknown
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- 2013-03-13 US US13/799,237 patent/US20130190375A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
CN101212899B (zh) | 2012-11-21 |
KR20080018912A (ko) | 2008-02-28 |
WO2006131221A3 (de) | 2007-08-23 |
US8431600B2 (en) | 2013-04-30 |
TW200715967A (en) | 2007-05-01 |
WO2006131221A2 (de) | 2006-12-14 |
BRPI0613488B1 (pt) | 2016-04-12 |
JP2008545763A (ja) | 2008-12-18 |
US20130190375A1 (en) | 2013-07-25 |
US20090105311A1 (en) | 2009-04-23 |
EP1890540A2 (de) | 2008-02-27 |
BRPI0613488A2 (pt) | 2011-01-11 |
DE102005025989A1 (de) | 2007-01-11 |
AR054280A1 (es) | 2007-06-13 |
CN101212899A (zh) | 2008-07-02 |
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