JP2006515366A - 置換環式ジカルボニラル化合物及び薬害軽減剤を主成分とする選択性除草剤 - Google Patents
置換環式ジカルボニラル化合物及び薬害軽減剤を主成分とする選択性除草剤 Download PDFInfo
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- JP2006515366A JP2006515366A JP2006500521A JP2006500521A JP2006515366A JP 2006515366 A JP2006515366 A JP 2006515366A JP 2006500521 A JP2006500521 A JP 2006500521A JP 2006500521 A JP2006500521 A JP 2006500521A JP 2006515366 A JP2006515366 A JP 2006515366A
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- Prior art keywords
- alkyl
- substituted
- optionally
- alkoxy
- halogen
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- 150000001875 compounds Chemical class 0.000 title claims description 119
- 239000004009 herbicide Substances 0.000 title abstract description 15
- 125000004122 cyclic group Chemical group 0.000 title description 3
- -1 cyclic dicarbonyl compound Chemical class 0.000 claims abstract description 177
- 239000000203 mixture Substances 0.000 claims abstract description 47
- 238000000034 method Methods 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 191
- 229910052739 hydrogen Inorganic materials 0.000 claims description 130
- 239000001257 hydrogen Substances 0.000 claims description 130
- 150000002431 hydrogen Chemical class 0.000 claims description 75
- 125000003545 alkoxy group Chemical group 0.000 claims description 71
- 239000000460 chlorine Substances 0.000 claims description 65
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 63
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 53
- 229910052801 chlorine Inorganic materials 0.000 claims description 53
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 49
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical class [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 46
- 229910052736 halogen Inorganic materials 0.000 claims description 46
- 150000002367 halogens Chemical class 0.000 claims description 45
- 229910052760 oxygen Inorganic materials 0.000 claims description 40
- 239000001301 oxygen Substances 0.000 claims description 40
- 229910052794 bromium Inorganic materials 0.000 claims description 39
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 38
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 37
- 229910052717 sulfur Chemical group 0.000 claims description 35
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 34
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 32
- 239000011593 sulfur Chemical group 0.000 claims description 32
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 239000011737 fluorine Substances 0.000 claims description 28
- 229910052731 fluorine Inorganic materials 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000001188 haloalkyl group Chemical group 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 21
- 125000006413 ring segment Chemical group 0.000 claims description 21
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 20
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 20
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 19
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical compound CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 9
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- QWWHRELOCZEQNZ-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC11CCCCC1 QWWHRELOCZEQNZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- VYNOULHXXDFBLU-UHFFFAOYSA-N Cumyluron Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)NCC1=CC=CC=C1Cl VYNOULHXXDFBLU-UHFFFAOYSA-N 0.000 claims description 6
- GMBRUAIJEFRHFQ-UHFFFAOYSA-N Fenchlorazole-ethyl Chemical compound N1=C(C(=O)OCC)N=C(C(Cl)(Cl)Cl)N1C1=CC=C(Cl)C=C1Cl GMBRUAIJEFRHFQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 5
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- FOMHMPJALXOZGZ-UHFFFAOYSA-N 2,2-dichloro-1-(2,2-dimethyl-1,3-oxazolidin-3-yl)ethanone Chemical compound CC1(C)OCCN1C(=O)C(Cl)Cl FOMHMPJALXOZGZ-UHFFFAOYSA-N 0.000 claims description 4
- MCNOFYBITGAAGM-UHFFFAOYSA-N 2,2-dichloro-1-[5-(furan-2-yl)-2,2-dimethyl-1,3-oxazolidin-3-yl]ethanone Chemical compound C1N(C(=O)C(Cl)Cl)C(C)(C)OC1C1=CC=CO1 MCNOFYBITGAAGM-UHFFFAOYSA-N 0.000 claims description 4
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 claims description 4
- 239000002794 2,4-DB Substances 0.000 claims description 4
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 4
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 claims description 4
- OHXLAOJLJWLEIP-UHFFFAOYSA-N 2-(dichloromethyl)-2-methyl-1,3-dioxolane Chemical compound ClC(Cl)C1(C)OCCO1 OHXLAOJLJWLEIP-UHFFFAOYSA-N 0.000 claims description 4
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 claims description 4
- YNQSILKYZQZHFJ-UHFFFAOYSA-N R-29148 Chemical compound CC1CN(C(=O)C(Cl)Cl)C(C)(C)O1 YNQSILKYZQZHFJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- MKQSWTQPLLCSOB-UHFFFAOYSA-N benzyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate Chemical compound N1=C(Cl)SC(C(=O)OCC=2C=CC=CC=2)=C1C(F)(F)F MKQSWTQPLLCSOB-UHFFFAOYSA-N 0.000 claims description 4
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 4
- LPVVTHQFIVXMEZ-UHFFFAOYSA-N diethyl 2-(5-chloroquinolin-8-yl)oxypropanedioate Chemical compound C1=CN=C2C(OC(C(=O)OCC)C(=O)OCC)=CC=C(Cl)C2=C1 LPVVTHQFIVXMEZ-UHFFFAOYSA-N 0.000 claims description 4
- JCHMGYRXQDASJE-UHFFFAOYSA-N metcamifen Chemical compound C1=CC(NC(=O)NC)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1OC JCHMGYRXQDASJE-UHFFFAOYSA-N 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical compound C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- MYINVIIJFQKURV-UHFFFAOYSA-N (2-chlorophenyl) 3-phenyl-1H-pyrazole-5-carboxylate Chemical compound ClC1=C(C=CC=C1)OC(=O)C1=NNC(=C1)C1=CC=CC=C1 MYINVIIJFQKURV-UHFFFAOYSA-N 0.000 claims description 2
- SODPIMGUZLOIPE-UHFFFAOYSA-N (4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 claims description 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 2
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 2
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 2
- VXJKYWLPNZBSMY-UHFFFAOYSA-N 1,1-dimethyl-3-[4-(naphthalen-1-ylsulfamoyl)phenyl]urea Chemical compound C1=CC(NC(=O)N(C)C)=CC=C1S(=O)(=O)NC1=CC=CC2=CC=CC=C12 VXJKYWLPNZBSMY-UHFFFAOYSA-N 0.000 claims description 2
- MHULQDZDXMHODA-UHFFFAOYSA-N 1-(2,2-dichloroacetyl)-3,3,8a-trimethyl-2,4,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-6-one Chemical compound C1C(C)(C)CN(C(=O)C(Cl)Cl)C2(C)N1C(=O)CC2 MHULQDZDXMHODA-UHFFFAOYSA-N 0.000 claims description 2
- AHXUVTKVCMOKIX-UHFFFAOYSA-N 1-bromo-4-(chloromethylsulfonyl)benzene Chemical compound ClCS(=O)(=O)C1=CC=C(Br)C=C1 AHXUVTKVCMOKIX-UHFFFAOYSA-N 0.000 claims description 2
- ZAWPDPLWGKAAHU-UHFFFAOYSA-N 2,2-dichloro-n-[2-oxo-2-(prop-2-enylamino)ethyl]-n-prop-2-enylacetamide Chemical compound ClC(Cl)C(=O)N(CC=C)CC(=O)NCC=C ZAWPDPLWGKAAHU-UHFFFAOYSA-N 0.000 claims description 2
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 claims description 2
- AXHCGXRBOHBEQA-UHFFFAOYSA-N 2-(5-chloro-2-methylphenoxy)acetic acid Chemical compound CC1=CC=C(Cl)C=C1OCC(O)=O AXHCGXRBOHBEQA-UHFFFAOYSA-N 0.000 claims description 2
- KWGQOJWITMQEOT-UHFFFAOYSA-N 2-benzhydryloxyacetic acid Chemical compound C=1C=CC=CC=1C(OCC(=O)O)C1=CC=CC=C1 KWGQOJWITMQEOT-UHFFFAOYSA-N 0.000 claims description 2
- LOHXCLHVVJGTLU-UHFFFAOYSA-N 2-oxopropyl 2-(5-chloroquinolin-8-yl)oxyacetate Chemical compound C1=CN=C2C(OCC(=O)OCC(=O)C)=CC=C(Cl)C2=C1 LOHXCLHVVJGTLU-UHFFFAOYSA-N 0.000 claims description 2
- OMKXSWYZPVQWRO-UHFFFAOYSA-N 2-prop-1-enyl-1-oxa-4-azaspiro[4.5]decane-4-carbodithioic acid Chemical compound CC=CC1CN(C2(O1)CCCCC2)C(=S)S OMKXSWYZPVQWRO-UHFFFAOYSA-N 0.000 claims description 2
- SIYAHZSHQIPQLY-UHFFFAOYSA-N 4-(4-chlorophenoxy)butanoic acid Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1 SIYAHZSHQIPQLY-UHFFFAOYSA-N 0.000 claims description 2
- YJJIKUFGJJZYIX-UHFFFAOYSA-N 4-(5-chloro-2-methylphenyl)butanoic acid Chemical compound CC1=CC=C(Cl)C=C1CCCC(O)=O YJJIKUFGJJZYIX-UHFFFAOYSA-N 0.000 claims description 2
- ZAYKVYVNMLEAMI-UHFFFAOYSA-N 4-(carboxymethyl)-2,3-dihydrochromene-4-carboxylic acid Chemical compound C1=CC=C2C(CC(=O)O)(C(O)=O)CCOC2=C1 ZAYKVYVNMLEAMI-UHFFFAOYSA-N 0.000 claims description 2
- QMNWXSUXINMZIM-UHFFFAOYSA-N 4-methylpentan-2-yl 2-(5-chloroquinolin-8-yl)oxyacetate Chemical compound C1=CN=C2C(OCC(=O)OC(C)CC(C)C)=CC=C(Cl)C2=C1 QMNWXSUXINMZIM-UHFFFAOYSA-N 0.000 claims description 2
- PFJJMJDEVDLPNE-UHFFFAOYSA-N Benoxacor Chemical compound C1=CC=C2N(C(=O)C(Cl)Cl)C(C)COC2=C1 PFJJMJDEVDLPNE-UHFFFAOYSA-N 0.000 claims description 2
- PYKLUAIDKVVEOS-UHFFFAOYSA-N Cyometrinil Chemical compound N#CCON=C(C#N)C1=CC=CC=C1 PYKLUAIDKVVEOS-UHFFFAOYSA-N 0.000 claims description 2
- NNYRZQHKCHEXSD-UHFFFAOYSA-N Daimuron Chemical compound C1=CC(C)=CC=C1NC(=O)NC(C)(C)C1=CC=CC=C1 NNYRZQHKCHEXSD-UHFFFAOYSA-N 0.000 claims description 2
- 239000005504 Dicamba Substances 0.000 claims description 2
- NRFQZTCQAYEXEE-UHFFFAOYSA-N Fenclorim Chemical compound ClC1=CC(Cl)=NC(C=2C=CC=CC=2)=N1 NRFQZTCQAYEXEE-UHFFFAOYSA-N 0.000 claims description 2
- 239000005574 MCPA Substances 0.000 claims description 2
- BWPYBAJTDILQPY-UHFFFAOYSA-N Methoxyphenone Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1=CC=CC(C)=C1 BWPYBAJTDILQPY-UHFFFAOYSA-N 0.000 claims description 2
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- ICJSJAJWTWPSBD-UHFFFAOYSA-N cloquintocet Chemical compound C1=CN=C2C(OCC(=O)O)=CC=C(Cl)C2=C1 ICJSJAJWTWPSBD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 2
- IVEMKPKJNOWXSK-UHFFFAOYSA-N ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate Chemical compound N1=C(C(=O)OCC)C=C(C)N1C1=CC=C(Cl)C=C1Cl IVEMKPKJNOWXSK-UHFFFAOYSA-N 0.000 claims description 2
- XORSBWXSVBDCCX-UHFFFAOYSA-N ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate Chemical compound C=1C=C(Cl)C=C(Cl)C=1N1N=C(C(=O)OCC)C=C1C1=CC=CC=C1 XORSBWXSVBDCCX-UHFFFAOYSA-N 0.000 claims description 2
- XQTFGOSTLPHBRA-UHFFFAOYSA-N ethyl 1-(2,4-dichlorophenyl)-5-propan-2-ylpyrazole-3-carboxylate Chemical compound N1=C(C(=O)OCC)C=C(C(C)C)N1C1=CC=C(Cl)C=C1Cl XQTFGOSTLPHBRA-UHFFFAOYSA-N 0.000 claims description 2
- JEMXUSHXYOXNFL-UHFFFAOYSA-N ethyl 2-(5-chloroquinolin-8-yl)oxyacetate Chemical compound C1=CN=C2C(OCC(=O)OCC)=CC=C(Cl)C2=C1 JEMXUSHXYOXNFL-UHFFFAOYSA-N 0.000 claims description 2
- VZZVOKHLRXJIEP-UHFFFAOYSA-N ethyl 2-benzhydryloxyacetate Chemical compound C=1C=CC=CC=1C(OCC(=O)OCC)C1=CC=CC=C1 VZZVOKHLRXJIEP-UHFFFAOYSA-N 0.000 claims description 2
- SQFPMCDRPGJOQH-UHFFFAOYSA-N ethyl 5-(4-fluorophenyl)-5-phenyl-4h-1,2-oxazole-3-carboxylate Chemical compound C1C(C(=O)OCC)=NOC1(C=1C=CC(F)=CC=1)C1=CC=CC=C1 SQFPMCDRPGJOQH-UHFFFAOYSA-N 0.000 claims description 2
- ZKDUJUNNBWZZCO-UHFFFAOYSA-N ethyl 5-[(2,4-dichlorophenyl)methyl]-4,5-dihydro-1,2-oxazole-3-carboxylate Chemical compound C1C(C(=O)OCC)=NOC1CC1=CC=C(Cl)C=C1Cl ZKDUJUNNBWZZCO-UHFFFAOYSA-N 0.000 claims description 2
- YNZGZAJXHXGDBF-UHFFFAOYSA-N ethyl 5-phenyl-4,5-dihydro-1,2-oxazole-3-carboxylate Chemical compound C1C(C(=O)OCC)=NOC1C1=CC=CC=C1 YNZGZAJXHXGDBF-UHFFFAOYSA-N 0.000 claims description 2
- WWHBBYNEFXJGME-UHFFFAOYSA-N ethyl 5-tert-butyl-1-(2,4-dichlorophenyl)pyrazole-3-carboxylate Chemical compound N1=C(C(=O)OCC)C=C(C(C)(C)C)N1C1=CC=C(Cl)C=C1Cl WWHBBYNEFXJGME-UHFFFAOYSA-N 0.000 claims description 2
- COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical compound C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims description 2
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims description 2
- RMIODHQZRUFFFF-UHFFFAOYSA-M methoxyacetate Chemical compound COCC([O-])=O RMIODHQZRUFFFF-UHFFFAOYSA-M 0.000 claims description 2
- NDQZMBNEHYSVPL-UHFFFAOYSA-N methyl 2-(5-chloroquinolin-8-yl)oxyacetate Chemical compound C1=CN=C2C(OCC(=O)OC)=CC=C(Cl)C2=C1 NDQZMBNEHYSVPL-UHFFFAOYSA-N 0.000 claims description 2
- WFVUIONFJOAYPK-UHFFFAOYSA-N n-(1,3-dioxolan-2-ylmethoxy)benzenecarboximidoyl cyanide Chemical compound C=1C=CC=CC=1C(C#N)=NOCC1OCCO1 WFVUIONFJOAYPK-UHFFFAOYSA-N 0.000 claims description 2
- NYDKNJDNBUFWRJ-UHFFFAOYSA-N n-[4-(dimethylcarbamoylamino)phenyl]sulfonyl-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)C1=CC=C(NC(=O)N(C)C)C=C1 NYDKNJDNBUFWRJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 12
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- ITGSCCPVERXFGN-UHFFFAOYSA-N isoxadifen Chemical compound C1C(C(=O)O)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 ITGSCCPVERXFGN-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
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- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000000280 phytoalexin Substances 0.000 description 1
- 150000001857 phytoalexin derivatives Chemical class 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 238000003976 plant breeding Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
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- 239000003531 protein hydrolysate Substances 0.000 description 1
- 210000001938 protoplast Anatomy 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
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- 230000001850 reproductive effect Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 150000003463 sulfur Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002025 wood fiber Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10301806A DE10301806A1 (de) | 2003-01-20 | 2003-01-20 | Selektive Herbizide auf Basis von substituierten, cyclischen Dicarbonylverbindungen und Safenern |
| PCT/EP2004/000038 WO2004064520A1 (de) | 2003-01-20 | 2004-01-07 | Selektive herbizide auf basis von substituierten, cyclischen dicarbonylverbindungen und safenern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006515366A true JP2006515366A (ja) | 2006-05-25 |
| JP2006515366A5 JP2006515366A5 (enExample) | 2007-03-01 |
Family
ID=32602705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006500521A Pending JP2006515366A (ja) | 2003-01-20 | 2004-01-07 | 置換環式ジカルボニラル化合物及び薬害軽減剤を主成分とする選択性除草剤 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US20060160703A1 (enExample) |
| EP (1) | EP1587367B1 (enExample) |
| JP (1) | JP2006515366A (enExample) |
| KR (1) | KR20050094441A (enExample) |
| CN (1) | CN100591208C (enExample) |
| AR (1) | AR043689A1 (enExample) |
| AT (1) | ATE362703T1 (enExample) |
| AU (1) | AU2004206721B9 (enExample) |
| BR (1) | BRPI0406825A (enExample) |
| CA (1) | CA2513510C (enExample) |
| DE (2) | DE10301806A1 (enExample) |
| ES (1) | ES2286591T3 (enExample) |
| MX (1) | MXPA05007656A (enExample) |
| PL (1) | PL208294B1 (enExample) |
| PT (1) | PT1587367E (enExample) |
| UA (1) | UA81461C2 (enExample) |
| WO (1) | WO2004064520A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008506739A (ja) * | 2004-07-20 | 2008-03-06 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 置換環状ジカルボニル化合物および薬害軽減剤に基づく選択的殺虫剤および／または殺ダニ剤 |
| WO2008096398A1 (ja) * | 2007-02-02 | 2008-08-14 | Kumiai Chemical Industry Co., Ltd. | 除草剤組成物 |
| JP2011527293A (ja) * | 2008-07-09 | 2011-10-27 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 植物成長調節剤 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10337496A1 (de) * | 2003-08-14 | 2005-04-14 | Bayer Cropscience Ag | 4-Biphenylsubstituierte-4-substituierte-pyrazolidin-3,5-dione |
| US20080200499A1 (en) * | 2004-07-20 | 2008-08-21 | Reiner Fischer | Selective Insecticides and/or Acaricides Based on Substituted Cyclic Dicarbonyl Compounds and Safeners |
| DE102004044827A1 (de) * | 2004-09-16 | 2006-03-23 | Bayer Cropscience Ag | Jod-phenylsubstituierte cyclische Ketoenole |
| DE102005059471A1 (de) * | 2005-12-13 | 2007-07-12 | Bayer Cropscience Ag | Herbizide Zusammensetzungen mit verbesserter Wirkung |
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| WO2001017351A1 (en) * | 1999-09-07 | 2001-03-15 | Syngenta Participations Ag | Herbicidal composition |
| JP2001510144A (ja) * | 1997-07-16 | 2001-07-31 | ゼネカ・リミテッド | テトラゾリノン除草剤およびそれに対する解毒剤の除草組成物 |
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| JP2002540104A (ja) * | 1999-03-20 | 2002-11-26 | アベンティス・クロップサイエンス・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | ２，４−ジアミノ−１，３，５−トリアジン、その調製方法および除草剤および植物成長調節剤としてのその使用 |
| JP2005508928A (ja) * | 2001-09-24 | 2005-04-07 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | スピロ環状３−フェニル−３−置換４−ケトラクタム類および４−ケトラクトン類 |
| JP2005516906A (ja) * | 2001-11-29 | 2005-06-09 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | ３−ビフェニル−置換−３−置換−４−ケトラクタムおよびケトラクトンならびにそれらの農薬としての利用 |
| JP2006503882A (ja) * | 2002-10-22 | 2006-02-02 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 農薬としての２−フェニル−２−置換−１，３−ジケトン類 |
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2003
- 2003-01-20 DE DE10301806A patent/DE10301806A1/de not_active Withdrawn
-
2004
- 2004-01-07 AT AT04700451T patent/ATE362703T1/de not_active IP Right Cessation
- 2004-01-07 BR BR0406825-4A patent/BRPI0406825A/pt not_active Application Discontinuation
- 2004-01-07 AU AU2004206721A patent/AU2004206721B9/en not_active Ceased
- 2004-01-07 PL PL377900A patent/PL208294B1/pl not_active IP Right Cessation
- 2004-01-07 ES ES04700451T patent/ES2286591T3/es not_active Expired - Lifetime
- 2004-01-07 CN CN200480007513A patent/CN100591208C/zh not_active Expired - Fee Related
- 2004-01-07 KR KR1020057013249A patent/KR20050094441A/ko not_active Ceased
- 2004-01-07 US US10/542,513 patent/US20060160703A1/en not_active Abandoned
- 2004-01-07 EP EP04700451A patent/EP1587367B1/de not_active Expired - Lifetime
- 2004-01-07 MX MXPA05007656A patent/MXPA05007656A/es active IP Right Grant
- 2004-01-07 PT PT04700451T patent/PT1587367E/pt unknown
- 2004-01-07 WO PCT/EP2004/000038 patent/WO2004064520A1/de not_active Ceased
- 2004-01-07 CA CA2513510A patent/CA2513510C/en not_active Expired - Fee Related
- 2004-01-07 DE DE502004003879T patent/DE502004003879D1/de not_active Expired - Lifetime
- 2004-01-07 JP JP2006500521A patent/JP2006515366A/ja active Pending
- 2004-01-07 UA UAA200508165A patent/UA81461C2/xx unknown
- 2004-01-20 AR ARP040100150A patent/AR043689A1/es unknown
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| JP2001510144A (ja) * | 1997-07-16 | 2001-07-31 | ゼネカ・リミテッド | テトラゾリノン除草剤およびそれに対する解毒剤の除草組成物 |
| WO1999020610A1 (en) * | 1997-10-21 | 1999-04-29 | Otsuka Kagaku Kabushiki Kaisha | 4-aryl-4-substituted pyrazolidine-3,5-dione derivatives |
| JP2000086628A (ja) * | 1998-09-11 | 2000-03-28 | Otsuka Chem Co Ltd | ３−アリール−３−置換−２，４−ジオン−５員環化合物、その製造法及び該化合物を含有する殺虫、殺ダニ剤 |
| JP2002540104A (ja) * | 1999-03-20 | 2002-11-26 | アベンティス・クロップサイエンス・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | ２，４−ジアミノ−１，３，５−トリアジン、その調製方法および除草剤および植物成長調節剤としてのその使用 |
| JP2003506352A (ja) * | 1999-07-30 | 2003-02-18 | バイエル アクチェンゲゼルシャフト | 有害生物防除剤としてのビフェニル−置換された環式ケトエノール類 |
| WO2001009092A1 (de) * | 1999-07-30 | 2001-02-08 | Bayer Aktiengesellschaft | Biphenylsubstituierte cyclische ketoenole als schädlingsbekämpfungsmittel |
| WO2001017351A1 (en) * | 1999-09-07 | 2001-03-15 | Syngenta Participations Ag | Herbicidal composition |
| WO2002063957A2 (de) * | 2001-02-12 | 2002-08-22 | Bayer Cropscience Ag | Selektive herbizide auf basis von substituierten arylketonen und safenern |
| JP2004529094A (ja) * | 2001-02-12 | 2004-09-24 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 置換アリールケトン及び薬害軽減剤に基づく選択的除草剤 |
| JP2005508928A (ja) * | 2001-09-24 | 2005-04-07 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | スピロ環状３−フェニル−３−置換４−ケトラクタム類および４−ケトラクトン類 |
| JP2005516906A (ja) * | 2001-11-29 | 2005-06-09 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | ３−ビフェニル−置換−３−置換−４−ケトラクタムおよびケトラクトンならびにそれらの農薬としての利用 |
| JP2006503882A (ja) * | 2002-10-22 | 2006-02-02 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 農薬としての２−フェニル−２−置換−１，３−ジケトン類 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008506739A (ja) * | 2004-07-20 | 2008-03-06 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 置換環状ジカルボニル化合物および薬害軽減剤に基づく選択的殺虫剤および／または殺ダニ剤 |
| WO2008096398A1 (ja) * | 2007-02-02 | 2008-08-14 | Kumiai Chemical Industry Co., Ltd. | 除草剤組成物 |
| JP2011527293A (ja) * | 2008-07-09 | 2011-10-27 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 植物成長調節剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2004206721B2 (en) | 2010-05-06 |
| ES2286591T3 (es) | 2007-12-01 |
| KR20050094441A (ko) | 2005-09-27 |
| DE502004003879D1 (de) | 2007-07-05 |
| US20060160703A1 (en) | 2006-07-20 |
| PT1587367E (pt) | 2007-08-03 |
| AU2004206721B9 (en) | 2010-06-10 |
| EP1587367B1 (de) | 2007-05-23 |
| DE10301806A1 (de) | 2004-07-29 |
| ATE362703T1 (de) | 2007-06-15 |
| UA81461C2 (en) | 2008-01-10 |
| PL208294B1 (pl) | 2011-04-29 |
| CN100591208C (zh) | 2010-02-24 |
| CN1761396A (zh) | 2006-04-19 |
| PL377900A1 (pl) | 2006-02-20 |
| AR043689A1 (es) | 2005-08-10 |
| EP1587367A1 (de) | 2005-10-26 |
| WO2004064520A1 (de) | 2004-08-05 |
| CA2513510C (en) | 2011-05-10 |
| AU2004206721A1 (en) | 2004-08-05 |
| BRPI0406825A (pt) | 2005-12-27 |
| CA2513510A1 (en) | 2004-08-05 |
| MXPA05007656A (es) | 2005-09-30 |
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