WO2008075743A1 - 除草剤組成物 - Google Patents
除草剤組成物 Download PDFInfo
- Publication number
- WO2008075743A1 WO2008075743A1 PCT/JP2007/074569 JP2007074569W WO2008075743A1 WO 2008075743 A1 WO2008075743 A1 WO 2008075743A1 JP 2007074569 W JP2007074569 W JP 2007074569W WO 2008075743 A1 WO2008075743 A1 WO 2008075743A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- component
- optionally substituted
- substituted
- alkyl
- Prior art date
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- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 104
- 239000000203 mixture Substances 0.000 title claims abstract description 96
- 239000004009 herbicide Substances 0.000 title claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 74
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 43
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 38
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 38
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 33
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 21
- 239000004480 active ingredient Substances 0.000 claims abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 13
- 239000005618 Sulcotrione Substances 0.000 claims abstract description 9
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000002547 isoxazolines Chemical class 0.000 claims abstract description 8
- NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 8
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 8
- CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000005981 Imazaquin Substances 0.000 claims abstract description 7
- JLYFCTQDENRSOL-VIFPVBQESA-N dimethenamid-P Chemical compound COC[C@H](C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-VIFPVBQESA-N 0.000 claims abstract description 7
- 230000035784 germination Effects 0.000 claims abstract description 7
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000005510 Diuron Substances 0.000 claims abstract description 5
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000005499 Clomazone Substances 0.000 claims abstract description 4
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000005603 Prosulfocarb Substances 0.000 claims abstract description 3
- 239000005625 Tri-allate Substances 0.000 claims abstract description 3
- MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical compound CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 claims abstract description 3
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 claims abstract description 3
- -1 may be substituted Chemical group 0.000 claims description 201
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 39
- 125000001424 substituent group Chemical group 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 22
- 125000002252 acyl group Chemical group 0.000 claims description 21
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 15
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 14
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims description 13
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 239000011734 sodium Substances 0.000 claims description 11
- 229910052708 sodium Inorganic materials 0.000 claims description 11
- 159000000000 sodium salts Chemical class 0.000 claims description 11
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
- 239000004094 surface-active agent Substances 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 10
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 125000006823 (C1-C6) acyl group Chemical group 0.000 claims description 7
- 239000005562 Glyphosate Substances 0.000 claims description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- IIPZYDQGBIWLBU-UHFFFAOYSA-N Dinoterb Chemical compound CC(C)(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O IIPZYDQGBIWLBU-UHFFFAOYSA-N 0.000 claims description 6
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 5
- JLYFCTQDENRSOL-UHFFFAOYSA-N 2-chloro-N-(2,4-dimethylthiophen-3-yl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound COCC(C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-UHFFFAOYSA-N 0.000 claims description 5
- 239000005476 Bentazone Substances 0.000 claims description 5
- 239000005614 Quizalofop-P-ethyl Substances 0.000 claims description 5
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 5
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 5
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 5
- 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
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- WGVWLKXZBUVUAM-UHFFFAOYSA-N Pentanochlor Chemical compound CCCC(C)C(=O)NC1=CC=C(C)C(Cl)=C1 WGVWLKXZBUVUAM-UHFFFAOYSA-N 0.000 claims description 4
- UNLYSVIDNRIVFJ-UHFFFAOYSA-N Piperophos Chemical compound CCCOP(=S)(OCCC)SCC(=O)N1CCCCC1C UNLYSVIDNRIVFJ-UHFFFAOYSA-N 0.000 claims description 4
- CNILNQMBAHKMFS-UHFFFAOYSA-M Pyrithiobac-sodium Chemical compound [Na+].COC1=CC(OC)=NC(SC=2C(=C(Cl)C=CC=2)C([O-])=O)=N1 CNILNQMBAHKMFS-UHFFFAOYSA-M 0.000 claims description 4
- YIJZJEYQBAAWRJ-UHFFFAOYSA-N Thiazopyr Chemical compound N1=C(C(F)F)C(C(=O)OC)=C(CC(C)C)C(C=2SCCN=2)=C1C(F)(F)F YIJZJEYQBAAWRJ-UHFFFAOYSA-N 0.000 claims description 4
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 claims description 4
- OSUHJPCHFDQAIT-UHFFFAOYSA-N ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-UHFFFAOYSA-N 0.000 claims description 4
- 229940097068 glyphosate Drugs 0.000 claims description 4
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- OSUHJPCHFDQAIT-GFCCVEGCSA-N quizalofop-P-ethyl Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-GFCCVEGCSA-N 0.000 claims description 4
- 125000003003 spiro group Chemical group 0.000 claims description 4
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 3
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 3
- MZHCENGPTKEIGP-RXMQYKEDSA-N (R)-dichlorprop Chemical compound OC(=O)[C@@H](C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-RXMQYKEDSA-N 0.000 claims description 3
- HKELWJONQIFBPO-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-(trichloromethyl)-1,2,4-triazole-3-carboxylic acid Chemical compound N1=C(C(=O)O)N=C(C(Cl)(Cl)Cl)N1C1=CC=C(Cl)C=C1Cl HKELWJONQIFBPO-UHFFFAOYSA-N 0.000 claims description 3
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 claims description 3
- ABOOPXYCKNFDNJ-UHFFFAOYSA-N 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-UHFFFAOYSA-N 0.000 claims description 3
- NEKULYKCZPJMMJ-UHFFFAOYSA-N 5-chloro-N-{1-[4-(difluoromethoxy)phenyl]propyl}-6-methylpyrimidin-4-amine Chemical compound C=1C=C(OC(F)F)C=CC=1C(CC)NC1=NC=NC(C)=C1Cl NEKULYKCZPJMMJ-UHFFFAOYSA-N 0.000 claims description 3
- PVSGXWMWNRGTKE-UHFFFAOYSA-N 5-methyl-2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=C(C)C=C1C(O)=O PVSGXWMWNRGTKE-UHFFFAOYSA-N 0.000 claims description 3
- HZKBYBNLTLVSPX-UHFFFAOYSA-N 6-[(6,6-dimethyl-5,7-dihydropyrrolo[2,1-c][1,2,4]thiadiazol-3-ylidene)amino]-7-fluoro-4-prop-2-ynyl-1,4-benzoxazin-3-one Chemical compound C#CCN1C(=O)COC(C=C2F)=C1C=C2N=C1SN=C2CC(C)(C)CN21 HZKBYBNLTLVSPX-UHFFFAOYSA-N 0.000 claims description 3
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 claims description 3
- JDWQITFHZOBBFE-UHFFFAOYSA-N Benzofenap Chemical compound C=1C=C(Cl)C(C)=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=C(C)C=C1 JDWQITFHZOBBFE-UHFFFAOYSA-N 0.000 claims description 3
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 3
- YUBJPYNSGLJZPQ-UHFFFAOYSA-N Dithiopyr Chemical compound CSC(=O)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=O)SC)=C1CC(C)C YUBJPYNSGLJZPQ-UHFFFAOYSA-N 0.000 claims description 3
- NRFQZTCQAYEXEE-UHFFFAOYSA-N Fenclorim Chemical compound ClC1=CC(Cl)=NC(C=2C=CC=CC=2)=N1 NRFQZTCQAYEXEE-UHFFFAOYSA-N 0.000 claims description 3
- 239000005570 Isoxaben Substances 0.000 claims description 3
- 239000005578 Mesotrione Substances 0.000 claims description 3
- 239000005579 Metamitron Substances 0.000 claims description 3
- LKJPSUCKSLORMF-UHFFFAOYSA-N Monolinuron Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C=C1 LKJPSUCKSLORMF-UHFFFAOYSA-N 0.000 claims description 3
- 239000005600 Propaquizafop Substances 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims description 3
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 3
- RUCAXVJJQQJZGU-UHFFFAOYSA-M hydron;2-(phosphonatomethylamino)acetate;trimethylsulfanium Chemical compound C[S+](C)C.OP(O)(=O)CNCC([O-])=O RUCAXVJJQQJZGU-UHFFFAOYSA-M 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 3
- PMHURSZHKKJGBM-UHFFFAOYSA-N isoxaben Chemical compound O1N=C(C(C)(CC)CC)C=C1NC(=O)C1=C(OC)C=CC=C1OC PMHURSZHKKJGBM-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 claims description 3
- KPUREKXXPHOJQT-UHFFFAOYSA-N mesotrione Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O KPUREKXXPHOJQT-UHFFFAOYSA-N 0.000 claims description 3
- VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 claims description 3
- 229960002939 metizoline Drugs 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 claims description 3
- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 claims description 3
- IPPAUTOBDWNELX-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical group C1=C([N+]([O-])=O)C(C(=O)OCC(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 IPPAUTOBDWNELX-UHFFFAOYSA-N 0.000 claims description 2
- LNGRZPZKVUBWQV-UHFFFAOYSA-N (4-chloro-2-methylsulfonylphenyl)-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CS(=O)(=O)C1=CC(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 LNGRZPZKVUBWQV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- DARPYRSDRJYGIF-PTNGSMBKSA-N (Z)-3-ethoxy-2-naphthalen-2-ylsulfonylprop-2-enenitrile Chemical compound C1=CC=CC2=CC(S(=O)(=O)C(\C#N)=C/OCC)=CC=C21 DARPYRSDRJYGIF-PTNGSMBKSA-N 0.000 claims description 2
- BXKKQFGRMSOANI-UHFFFAOYSA-N 1-methoxy-3-[4-[(2-methoxy-2,4,4-trimethyl-3h-chromen-7-yl)oxy]phenyl]-1-methylurea Chemical compound C1=CC(NC(=O)N(C)OC)=CC=C1OC1=CC=C2C(C)(C)CC(C)(OC)OC2=C1 BXKKQFGRMSOANI-UHFFFAOYSA-N 0.000 claims description 2
- GOCUAJYOYBLQRH-UHFFFAOYSA-N 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-UHFFFAOYSA-N 0.000 claims description 2
- KRQUFUKTQHISJB-YYADALCUSA-N 2-[(E)-N-[2-(4-chlorophenoxy)propoxy]-C-propylcarbonimidoyl]-3-hydroxy-5-(thian-3-yl)cyclohex-2-en-1-one Chemical compound CCC\C(=N/OCC(C)OC1=CC=C(Cl)C=C1)C1=C(O)CC(CC1=O)C1CCCSC1 KRQUFUKTQHISJB-YYADALCUSA-N 0.000 claims description 2
- IRJQWZWMQCVOLA-ZBKNUEDVSA-N 2-[(z)-n-[(3,5-difluorophenyl)carbamoylamino]-c-methylcarbonimidoyl]pyridine-3-carboxylic acid Chemical compound N=1C=CC=C(C(O)=O)C=1C(/C)=N\NC(=O)NC1=CC(F)=CC(F)=C1 IRJQWZWMQCVOLA-ZBKNUEDVSA-N 0.000 claims description 2
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 claims description 2
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 claims description 2
- KZNDFYDURHAESM-UHFFFAOYSA-N 2-chloro-n-(2-ethyl-6-methylphenyl)-n-(propan-2-yloxymethyl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(COC(C)C)C(=O)CCl KZNDFYDURHAESM-UHFFFAOYSA-N 0.000 claims description 2
- LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 claims description 2
- CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 claims description 2
- ZUSHSDOEVHPTCU-UHFFFAOYSA-N 6-chloro-3-phenyl-1h-pyridazin-4-one Chemical compound N1C(Cl)=CC(=O)C(C=2C=CC=CC=2)=N1 ZUSHSDOEVHPTCU-UHFFFAOYSA-N 0.000 claims description 2
- 239000005470 Beflubutamid Substances 0.000 claims description 2
- QGQSRQPXXMTJCM-UHFFFAOYSA-N Benfuresate Chemical compound CCS(=O)(=O)OC1=CC=C2OCC(C)(C)C2=C1 QGQSRQPXXMTJCM-UHFFFAOYSA-N 0.000 claims description 2
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- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
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- 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
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- 235000011178 triphosphate Nutrition 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 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
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- 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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- 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
- A01N43/80—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 1,2
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
-
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
- A01N39/04—Aryloxy-acetic acids; Derivatives thereof
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
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- 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
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- 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
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
- A01N43/70—Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom
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- 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
- A01N43/82—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 three ring hetero atoms
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- 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
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
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- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
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- 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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
Definitions
- the present invention relates to a novel herbicidal composition.
- the compound consisting of an isoxazoline derivative or a salt thereof, which is [Component A] contained in the herbicidal composition of the present invention is rice, wheat, barley, corn, grain sorghum, diz, soybean, sugar beet.
- Patent Document 1 describes that it is safe for turf, fruit trees, etc. and has an excellent herbicidal effect by itself.
- the compound of [Component B] and [Component C] described later contained in the herbicidal composition of the present invention is a known compound having herbicidal activity, for example, non-patent documents; Are listed.
- Patent Document 2 describes an example in which a compound represented by the formula [I] and a known herbicide compound can be mixed.
- herbicides used for useful crops are applied to soil or foliage, exhibiting low herbage and sufficient herbicidal effects on a wide range of weed species, and exhibiting high selectivity between crops and weeds. It is desirable that it be a drug.
- Patent Document 1 WO2002 / 062770
- Patent Document 2 WO2004 / 014138
- Non-Patent Document 1 Pesticide Manual 13th edition, British Crop Council
- Non-Patent Document 2 Shibuya Index 12th Edition, 11th Edition (SHIBUYA INDEX 10th Edition, 11th Edition, Publisher: SHIBUYA INDEX Study Group)
- Non-Patent Document 3 Monthly Fine Chemicals, Volume 35, Issue 7 (2006) (CMC Publishing) Disclosure of Invention
- An object of the present invention is to provide a herbicidal composition comprising an isoxazoline derivative represented by the following formula [I] or a salt thereof for controlling unwanted weeds in the cultivation of useful crops or useful plants. It is in.
- the present inventors by combining two or more kinds of drugs, expanded the herbicidal spectrum as compared with the range of herbicidal application with each single agent, and at the same time, achieved the herbicidal effect at an early stage, and sustained the effect.
- the present inventors In addition to exerting a sufficient effect at a dose lower than that of a single agent, safety against rice, wheat, barley, corn, grain sorghum, soybeans, ivy, sugar beet, turf, fruit trees, etc. is also ensured.
- the inventors have found that a sufficient herbicidal effect can be achieved by a single treatment, and have completed the present invention.
- the present invention is characterized by having the following gist.
- Component A which is one or more compounds selected from the group force consisting of an isoxazoline derivative represented by the formula [I] described below and a salt thereof, and [Component A described below] And B] as an active ingredient.
- R 1 and R 2 independently represent a hydrogen atom, a C1-C10 alkyl group, a C3-C8 cycloalkyl group or a C3-C8 cycloalkyl C1-C3 alkyl group, or R 1 and R 2 Taken together, together with these bonded carbon atoms, shows a C3-C7 spiro ring;
- R 3 and R 4 independently represent a hydrogen atom, a C1-C10 alkyl group or a C3-C8 cycloalkyl group, or R 3 and R 4 together, together with these bonded carbon atoms C 3 to C 7 spiro ring; R 2 , R 3 and R 4 can form a 5- to 8-membered ring with these bonded carbon atoms,
- R 5 and R 6 independently represent a hydrogen atom or a C1-C10 alkyl group
- Y represents a 5- to 6-membered aromatic heterocyclic group or aromatic heterocyclic group having an arbitrary hetero atom selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom.
- the cyclic group may be substituted with 0 to 6 identical or different groups selected from the substituent group ⁇ , and adjacent alkyl groups, alkoxy groups, alkyl groups and alkoxy groups, alkyl groups.
- a group and an alkylthio group, an alkyl group and an alkylsulfonyl group, an alkyl group and a monoalkylamino group, or two alkyl groups and a dialkylamino group may be bonded to each other and substituted with 1 to 4 halogen atoms.
- a member ring may be formed, and when the hetero atom of these hetero ring groups is a nitrogen atom, it may be oxidized to become an oxyoxide.
- ⁇ represents an integer of 0-2.
- C3-C8 cycloalkyl group (this group may be substituted with a halogen atom or an alkyl group), C1-C10 alkoxy group, C1-C10 alkylthio group, C1-C10 alkyl sulfonyl group, C1-C10 alkoxycarbonyl group Group, C2-C6 haloalkenyl group, amino group (the nitrogen atom of the group is independently C1-C10 alkyl group, C1-C6 acyl group, C1-C4 neuroalkylcarbonyl group, C1-C10 alkylsulfonyl group) , A C1-C4 haloalkyl sulfonyl group may be substituted), a strong rubamoyl group (the nitrogen atom of the group may be independently substituted with a C1-C10 alkyl group), a C1-C6 acyl group, A C1-C4 haloalkylcarbony
- Clonnahop (clodinafop—propargyl), Nnoro Hoff 'Pychinole (cyhalofop-butyl), Diclohop-methinole (diclofop-methyl), Phenooxaprop-P-ethyl, fenoxaprop-P-ethyl, fenoxaprop-ethyl, fluazifop-but yl, funaleadihop ⁇ ⁇ (fluazifop- P-butyl), noroxyhop (haloxyfop), noroxyhop ⁇ ⁇ (haloxyfop- P), noroxyhop ⁇ ⁇ methinore (haloxyfop- P-methyl), metamihop (m etamifop ;, propaquizafop), salohop 'etenore, quizalofop-ethyl), quizalofop' P quizalofop-P) quizalofop-quizalof
- Amidosulibron azimsulforon, bensulfuron-methyl, chlorimuron-ethyl, chronoresnorefurono, chlorsulruron, cinosulfuron, cinosulfuron cyclosu lfamuron), etamethos noreflon 'methinole (ethametsulforon- methyl), ethoxy noreflon (ethoxysulfuron), flazas noreflon (flazasulfuron), funorepinores noreflon (flupyrsulfuron on), ios noreflon uodosulfulon — — Sodium, mesosus urefon methenore, mesosulf uron-methyl, methos no leflon.
- Imazamethabenz methyl, imazamox, imazapic (imazapic), imazaquin
- chloroxuron dimefuron, diuron, etizimron, ethidimuron, fenuron, fluometuron, isoproturon, isouron, methabenzthiazuron (methabenzthiazuron) m etobromuron, metoxuron, monolinuron, monolinuron, i, neb uron, siduron, tebuthiuron
- Cinidon ethyl
- funole microlac pentyl
- Phenylrubiazole compounds Pilafnorefen-ethyl, fluazolate
- Canolebetamid (carbetamide), Chronoleph Mouth Fam (chlorpropham), Profam (proph am j
- Acetochlor alachlor, butachlor, dimethachlor, dimethenamid, dimethenamid, metazac hlor, petoxamid, pretilachlor, proptilachlor pr opachlor), propisoclonole (propisochlor), S-metolaclonole (S— metolachlor), tennole crecronole (thenylchlorj)
- Difenzoquat framprop-M, bromobutide, oxaziclomefone, cinmethylin, etho Benzanide (etobenzanid), fosamine, cumyluron, diimron (d aimuron), menanore thyron, methy ⁇ dimuroru, inta, indanofan, piributicarb, pyrimisolephan (pyrimisulfan) , HC—252, Honorecronoreunuron (forchiorfenuron), Chinazuron (tnidiazuron), Hifusnorehotoronore, pyrasulfotole), Maleic hydrazide, diflumetorim, diflumetorim, fenclorim, ⁇ 1 ⁇ , ancymidol), ⁇ norepri ⁇ ⁇ nore (flurprimidol), kuronoremekoto (chiormequaU, mepiquatchloride),
- a herbicidal composition comprising:
- Component A is a 5-membered or 6-membered aromatic having a heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom in the formula [I] 2.
- Component A is represented by the formula [I], wherein Y is a thiophene 3-yl group, a pyrazonol 4-yl group, a pyrazole-5-yl group, an isoxazole-4-yl group, an isothiazole-4 2.
- the herbicidal composition according to 1 above which is a compound represented by an alkyl group, a pyridine-3-yl group, or a pyrimidine-5-yl group.
- Y is a pyrazole-4-yl group
- the substituent group ⁇ is hydrogen at the 3-position and 5-position and further at the 1-position of the pyrazole ring.
- the nitrogen atom is independently a C1-C10 alkyl group or an optionally substituted phenyl group, an amino group (the nitrogen atom of the group is independently a C1-C10 alkyl group, substituted Optionally substituted phenyl group, acyl group, C1-C4 haloalkylcarbonyl group, optionally substituted benzylcarbonyl group, optionally substituted benzoyl group, C1-C10 aralkylsulfonyl group, C1- C4 haloalkylsulfonyl group, optionally substituted benzylsulfonyl group or substituted! /, May! /, Substituted with phenylsulfonyl group! /! Must be substituted 2.
- the herbicidal composition according to 1 is independently a C1-C10 alkyl group or an optionally substituted phenyl group, an amino group (the nitrogen atom of the group is independently a C1-
- Component A is a compound represented by the formula [I], wherein Y is a pyrazole-5-yl group, the substituent group ⁇ is at the 4-position of the pyrazole ring, and further at the 1-position, C1 ⁇ C10 alkyl group, C1-C10 alkyl group, C1-C4 haloalkyl group, C3-C8 cycloalkyl group, C2-C6 alkenyl group, C2-C6 alkenyl group, mono-substituted with any group selected from the substituent group ⁇ Alkino group, C1-C10 alkylsulfinyl group, C1-C10 alkylsulfonyl group, C1-C10 alkylsulfonyl group monosubstituted with any group selected from substituent group ⁇ , C1-C4 haloalkylsulfonyl Group, an optionally substituted phenyl group, an optionally substituted aromatic heterocyclic group
- the nitrogen atom is independently a C1-C10 alkyl group or an optionally substituted phenyl group, an amino group (the nitrogen atom of the group is independently a C1-C10 alkyl group, substituted Optionally substituted phenyl group, acyl group, C1-C4 haloalkylcarbonyl group, optionally substituted benzylcarbonyl group, optionally substituted benzoyl group, C1-C10 alkylsulfonyl group, C1- C4 haloalkylsulfonyl group, which may be substituted! /, Benzylsulfonyl group or substituted! /, May! /, Substituted with phenylsulfonyl group! /, May! /, 2.
- the herbicidal composition according to 1 above which is necessarily a substituted compound
- R1 and R2 are methyl groups
- R3 and R4 are hydrogen atoms
- Y is a pyrazole-4-yl group
- the herbicidal composition according to 1, wherein the 5-position is independently a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 haloalkoxy group.
- Component A is 3 — [(5-Difluoromethoxy-1-methyl 3-trifluoromethylvirazole-4-ynole) methylsulfonyl] 4,5-dihydro-5,5-dimethylisoxazol 2.
- Component B is quizalofop-ethyl, quizalofop-p-ethyl, cetoxydim, pyrithiobac. Sodium salt, bispyribac. Sodium salt, pyrimisulphan, imazetapyr, imazaquin, chlorimlone echinore, duron, bentazone , Noraquat, Snorefentrazone, Flutiaset'Methyl, Sulcotrione, Norflurazon, Cromazone, Bialafos, Ashram, Furfenacet, Dimethenamid-P, Prosulfocalp, Thiobencalp, 2, 4-D, Cloviralide, Amethrin, Isoprolone A herbicide composition according to any one of the above;! To 8, which is one or more compounds selected from the group consisting of picolinaphene, trifnorelarin, acetoclonole, trialate, salts thereof, and analogs object.
- Component B is imazaquin, diuron, sulfentrazone, sulcotrione, norflurazon, clomazone, dimethenamide-P, prosulfocarp, isoprollone, trifluralin or triarate.
- a herbicidal composition comprising the herbicidal composition according to any one of 1 to 10 above and the following [Component C] as active ingredients. [0023] [Component C]:
- a herbicidal composition comprising the herbicidal composition according to any one of 1 to 10 above and the following [Component D] as active ingredients.
- a herbicidal composition comprising the above compound as an active ingredient.
- [0025] 13 It comprises the herbicidal composition as described in 11 above and one or more compounds selected from [Component D] as described in 12 above as active ingredients. Herbicide composition object. 14. [Component A]: [Component B] is contained in a weight ratio of 1: 0.001;
- herbicidal composition comprising at least one surfactant.
- the herbicidal composition of the present invention is not limited to a simple total of the activities obtained with each individual component, but synergistically exerts herbicidal and phytotoxicity-reducing effects, thus reducing the agricultural chemical application rate.
- the power to do S is suitable for various kinds of weeds in paddy fields, upland fields, non-agricultural fields, etc. that are highly safe for useful crops! Can be controlled.
- the notation such as C1 to C10 in this case indicates that the number of carbon atoms of the subsequent substituent is 1 to 10;
- a halogen atom shows a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
- a C1-C10 alkyl group means a straight or branched alkyl group having a carbon number;!
- -10 unless otherwise limited, and includes, for example, a methyl group, an ethyl group, an n-propyl group, an isopropylinole group, n --Butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, 3,3-dimethylbutyl, heptyl, Or an octyl group etc. can be mentioned.
- the C3 to C8 cycloalkyl group means a cycloalkyl group having 3 to 8 carbon atoms, for example, a force S that includes a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group.
- C3-C8 cycloalkyl C1-C3 alkyl group (this group may be substituted with a halogen atom or an alkyl group) is independently substituted with a halogen atom 1-4 or a C1-C3 alkyl group, unless otherwise limited
- a C1-C3 alkyl group substituted by a C3-C8 cycloalkyl group which may be, for example, a cyclopropylmethyl group, a 1-cyclopropylethyl group, a 2-cyclopropylethyl group, a 1-cyclopropylpropyl group; 2-cyclopropylpropynole group, 3-cyclopropylpropyl group, cyclobutylmethyl group, cyclopentylmethyl group, cyclohexylmethyl group, 2-chlorocyclopropylmethyl group, 2,2-dichlorocyclopropylmethyl group, 2- Examples include fluorocyclopropylmethyl group, 2,2-d
- the C1-C3 alkyl group refers to an alkyl group having 1 to 3 carbon atoms substituted by a cycloalkyl group having 3 to 8 carbon atoms, such as a cyclopropylmethyl group, a pill group, and 2-cyclopropyl. Examples thereof include a propyl group, a 3-cyclopropylpropyl group, a cyclobutylmethyl group, a cyclopentylmethyl group, and a cyclohexylmethyl group.
- a C1-C4 haloalkyl group independently represents a linear or branched alkyl group having 1 to 4 carbon atoms, which is substituted with a halogen atom 1 to 9, unless specifically limited.
- a fluoromethyl group, chloro examples thereof include a methyl group, a bromomethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, and a pentafluoroethyl group.
- the C2-C6 alkenyl group refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms, such as an ethyl group, a 1-propenyl group, a 2-propenyl group, and an isopropenyl group.
- a group S 1-Butul group, 2-Butul group, 3-Butul group, or 2-Pentul group etc.
- the C2-C6 alkynyl group means a straight-chain or branched alkynyl group having 2 to 6 carbon atoms, such as an ethur group, 2-propynyl group, 1-methyl-2-propynyl group, 2-butynyl group, 3 A butul group, a 2-methyl-3 butul group, etc. can be mentioned.
- the C2-C6 haloalkenyl group is independently a straight-chain or branched alkenyl group having 2 to 6 carbon atoms and substituted with a halogen atom;! To 4 unless otherwise specified, for example, 3 chloro- Examples thereof include 2-propenyl group and 2-chloro-2-propenyl group.
- the C1-C10 alkoxy group means an (alkyl) O- group in which the alkyl part has the above-mentioned meaning, for example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, tert-butoxy group, n-butoxy group Group, sec butoxy group, isobutoxy group and the like.
- C1-C4 haloalkoxy group means a (haloalkyl) O group in which the haloalkyl moiety has the above meaning, for example, a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, or 2 , 2,2-trifluoroethoxy group and the like.
- C3-C8 cycloalkyloxy group means (cycloalkyl) O group in which the cycloalkyl part has the above meaning, for example, cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group, or cyclo Examples include a hexyloxy group.
- the C1-C3 alkyloxy group means a (cycloalkylalkyl) O group in which the cycloalkylalkyl part has the above-mentioned meaning, for example, cyclopropylmethoxy group, 1-cyclopropylethoxy group, 2-cyclopropyl Examples thereof include an ethoxy group, a 1-hydroxy group, a cyclobutylmethoxy group, a cyclopentylmethoxy group, and a cyclohexylmethoxy group.
- C2-C6 alkenyloxy group and C2-C6 alkynyloxy group are alkenyl or Represents an (alkenyl) o- group or an (alkynyl) o- group in which the alkynyl moiety has the above-mentioned meaning.
- a 2-propenyloxy group, a 2-propynyloxy group, or the like can be used.
- C1 to C10 alkylthio group, 1 to 10 alkyl sulfinyl group and 1 to 10 alkyl sulfonyl group are (alkyl) S group, (alkyl) SO group, Alkyl) -S02- group, for example, methylthio group, ethylthio group, n-propylthio group, isopropylthio group, methylsulfifer group, methylsulfonanol group, ethylsulfonyl group, n-propylsulfonyl group, or isopropylsulfonyl group That power S.
- the C1-C10 alkylsulfonyloxy group means an (alkylsulfonyl) 2 O group in which the alkylsulfonyl moiety has the above meaning, and examples thereof include a methylsulfonyloxy group or an ethylsulfonyloxy group. .
- C1-C10 alkoxycarbonyl group means (alkoxy) -CO group in which the alkoxy moiety has the above meaning, for example, methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, etc. Can be mentioned.
- the C1-C6 acyl group represents a linear or branched aliphatic acyl group having from 6 to 6 carbon atoms, and includes, for example, a formyl group, a acetyl group, a propionyl group, an isopropionyl group, a butyryl group, or A bivaloyl group etc. can be mentioned.
- the C1-C10 acyloxy group represents a (acyl) O group in which the acyl moiety has the above-mentioned meaning, and examples thereof include an acetoxy group, a propionyloxy group, an isopropionyloxy group, and a bivalyloxy group. .
- C1-C4 haloalkylcarbonyl group, C1-C4 haloalkylthio group and C1-C4 noble alkylsulfonyl group have the same meaning as described above for (haloalkyl) — CO 2 group, (haloalkyl) 1 S group, (haloalkyl) 1 S02— represents, for example, chloroacetyl group, trifluoroacetyl group, pentafluoropropionyl group, difluoro group Examples thereof include a methylthio group, a trifluoromethylthio group, a chloromethylsulfonyl group, a difluoromethylsulfonyl group, and a trifluoromethylsulfonyl group.
- C1-C4 noroalkylcarbonyloxy group and C1-C4 haloalkylsulfonyloxy group are haloalkylcarbonyl moiety and haloalkylsulfonyl moiety as defined above (nozzle alkylcarbonyl) -O- group, (haloalkyl) (Sulfonyl) -O sulfonylsulfonyloxy group, trifluoromethylsulfonyloxy group, and the like.
- a phenyl group (which may be substituted), an aromatic heterocyclic group (which may be substituted), a (substituted), a phenoxy group, (a substituted! /, May! /) Aromatic heterocyclic group (optionally substituted), phenylthio group (optionally substituted), aromatic heterocyclic group (optionally substituted), (substituted) (Optionally) phenylsulfonyl group, (optionally substituted) phenylsulfonyloxy group, (substituted! /, May!
- Aromatic heterocyclic sulfonyl group (substituted) Benzylenocarbonyl group (optionally substituted), benzylcarbonyloxy group (optionally substituted), benzylsulfonyl group (optionally substituted), benzoyl group (optionally substituted), (substituted) Benzoyloxy group (may be substituted! /) ! /)) Benzyloxycarbonyl group or (substituted! /, May!
- Optionally substituted group” in the sulfonyl group is, for example, halogen atom, C1-C10 alkynole group C1-C4 haloalkyl group, C1-C10 alkoxyalkyl group, C1-C10 alkoxy group, C1-C10 alkylthio group, C1-C10 alkylsulfonyl group, C1-C6 acyl group, C1-C10 alkoxycarbonyl group, A cyano group, a strong rubamoyl group (the nitrogen atom of the group may be independently substituted with a C1-C10 alkyl group), a nitro group, or an amino group (the nitrogen atom of the group is independently C1 ⁇ C10 alkyl group, C1 to C6 acyl group, C1 to C4 haloalkylcarbonyl group, C1 to C10 alkylsulfonyl group, or C1 to C4 haloal
- a 5-membered, 6-membered aromatic heterocyclic group having a heteroatom arbitrarily selected from a nitrogen atom, an oxygen atom and a sulfur atom is, for example, furyl having 1 to 3 heteroatoms.
- the aromatic hetero-fused ring group refers to a group having 1 to 3 heteroatoms arbitrarily selected from a nitrogen atom, an oxygen atom and a sulfur atom, such as a benzofuryl group, a benzocenyl group, an indolyl group, Benzoxazolyl group, benzothiazolyl group, benzimidazolyl group, benzoisoxazolyl group, benzisothiazolyl group, indazolyl group, quinolyl group, isoquinolyl group, fusarajur group, quinoxalinyl group, quinazolinyl group, cinnolinyl group An azotriazolyl group can be mentioned.
- Aromatic heterocyclic group (Substituted! /, May! /,) Aromatic heterocyclic group, (Substituted! /, May! /,) Aromatic heterocyclic group, (Substituted ! /, May! /) Aromatic heterocyclic group or aromatic heterocyclic sulfonyl group (which may be substituted!
- /) May be nitrogen atom, oxygen atom And a 5- to 6-membered group having from 3 to 6 heteroatoms arbitrarily selected from sulfur atoms, such as furyl, chenyl, pyrrolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxazolyl A group, a thiazolyl group, an imidazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidyl group, a pyrazyl group, a triazinyl group, a triazolyl group, an oxadiazolyl group or a thiadiazolyl group.
- sulfur atoms such as furyl, chenyl, pyrrolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxazolyl A group, a thiazolyl group, an imidazolyl group, a pyrid
- a pharmacologically acceptable salt is a salt of a compound having the formula [I] and a metal or an organic base, when a hydroxyl group, a carboxynole group, an amino group or the like is present in the structure, or It is a salt with a mineral acid or an organic acid.
- the metal include an alkali metal such as sodium or potassium, or an alkaline earth metal such as magnesium or calcium.
- the organic base include triethylamine or diisopropylamine.
- mineral acids include hydrochloric acid and sulfuric acid
- examples of organic acids include acetic acid, methanesulfonic acid, and p-toluenesulfonic acid.
- Pr n propyl group
- Pr-i isopropyl group
- Pr- C Cyclopropyl group
- Bu n Butinole group
- Bu- -i iso Butinole group
- Bu— s sec Butinole group
- Bu- -t tert Butinole group: Cycloputinole group
- Pen n Pentinole group
- Pen— c Cyclopentyl group
- Hex n Hexinole group
- Hex—c Cyclohexenole group
- (4 Cl) Ph represents a 4-chloro 1-port phenyl group
- 3-Hex represents a 3-hexyl group
- this invention compound contains a hydroxyl group as a substituent, there exists a compound which has a ketoeenol tautomer, However, Any isomer and its mixture are also contained in this invention compound.
- R1 and R2 are independently a methyl group or an ethyl group
- R3, R4, R5 and R6 are hydrogen atoms, n is an integer of 2;
- Y is a thiophene 3yl group (wherein the 2-position and 4-position of the group are a halogen atom, an alkyl group, a haloalkyl group, an alkoxyalkyl group, a cycloalkyl group, an alkoxy group, a haloalkoxy group, an acyl group, a haloalkylcarbonyl group) , An alkoxycarbonyl group, a cyano group or a strong rubamoyl group (the nitrogen atom of the group may be independently substituted with an alkyl group).
- Pyrazole-4-yl group (wherein the 3-position and 5-position of the group are a halogen atom, an alkyl group, a neuroalkyl group, an alkoxyalkyl group, a cycloalkyl group, an alkoxy group, a normal group, A alkoxy group, a cycloalkylalkyloxy group, an optionally substituted phenoxy group, an alkylthio group, an alkylsulfonyl group, an acyl group, a haloalkylcarbonyl group, an alkoxycarbonyl group, a cyano group, or a strong rubamoyl group (of the group).
- a nitrogen atom may be independently substituted with an alkyl group), but in addition, a hydrogen atom, an alkyl group, an alkyl group monosubstituted with an arbitrary group selected from the substituent group ⁇ , a haloalkyl group at the 1-position ,
- Pyrazole-5-yl group (wherein the 4-position of the group is a halogen atom, an ano- quinole group, a haloalkino group, an alkoxyalkyl group, a haloalkoxy group, an acyl group, a haloalkylcarbonyl group, an alkoxycarbonyl group, a cyano group or a force)
- Rubamoyl group (the nitrogen atom of the group may be independently substituted with an alkyl group).
- the 1-position is mono-substituted with an arbitrary group selected from a hydrogen atom, an alkyl group, and a substituent group ⁇ .
- An alkyl group, a haloalkyl group, a cycloalkyl group or an optionally substituted phenyl group must be substituted.
- An isoxazole-4-yl group (the 3-position and 5-position of the group are a halogen atom, an alkyl group) , Haloalkyl group, alkoxyalkyl group, cycloalkyl group, alkoxy group, haloalkoxy group, alkylthio group, alkylsulfonyl group, Group, haloalkyl Cal Boniru group, an alkoxycarbonyl group, Shiano group or force Rubamoiru group (the nitrogen atom of said group may be substituted with an alkyl group independently) is always replaced).;
- Isothiazole-4-yl group (the 3-position and 5-position of the group are a halogen atom, an alkyl group, a haloalkyl group, an alkoxyalkyl group, a cycloalkyl group, an alkoxy group, a nitroalkoxy group, an optionally substituted phenoxy group, Alkylthio group, alkylsulfonyl group A group, an acyl group, a haloalkylcarbonyl group, an alkoxycarbonyl group, a cyano group, a carbamoyl group (the nitrogen atom of the group is independently substituted with an alkyl group! /, May! /). );
- Pyridine 3yl group (the 2-position and 4-position of the group are a halogen atom, an alkyl group, a haloalkino group, an alkoxyalkyl group, a cycloalkyl group, an alkoxy group, a haloalkoxy group, an alkylthio group, an alkylsulfonyl group, an acyl group) , A haloalkylcarbonyl group, an alkoxycarbonyl group, a cyano group, or a strong rubamoyl group (the nitrogen atom of the group may be independently substituted with an alkyl group), or
- Pyrimidine 5-yl group (the 4- and 6-positions of the group are a halogen atom, an alkyl group, a halo alkenyl group, an alkoxyalkyl group, a cycloalkyl group, an alkoxy group, a haloalkoxy group, an alkylthio group, an alkylsulfonyl group, an acyl A group, a haloalkylcarbonyl group, an alkoxycarbonyl group, a cyano group or a strong rubamoyl group (the nitrogen atom of the group is independently substituted with an alkyl group! /, May! /). Isoxazoline derivative or a salt thereof.
- herbicide compounds as [Component A] are compound Nos. 3-0054.
- the compound represented by the formula [I] can be produced by the method described in Patent Document 1 or a method analogous thereto.
- Preferred herbicide compounds as [Component B] are quizalofop-P-ethyl, cetoxydim, pirithiobac sodium, bispyrivacnatrim, pyrimylsulfan, imazetapyr, imazaquin, chlorimlone ethinore, deyuron, bentazone. , Noraquat, Snorefentrazone, Flutiaset methyl, Sulcotrione, Norflurazon, Cromazone, Bialaphos, Ashram, Fluenaset, Dimethenamide P, Sulfentrazone, Tiobencalp, 2, 4 D and Cloviralide and their salts, Analogs such as acids, esters and amides
- the herbicidal composition of the present invention is generally as follows, although it depends on the relative activity of each component.
- [Component A] is from 0.001 to 100 parts by weight, preferably from 0.01 to 50 parts by weight, more preferably from 0.05 to 30 parts by weight, based on 1 part by weight of [Component A].
- Min D] is 0.0;! To 100 parts by weight, preferably 0.05 to 30 parts by weight.
- [Component B] is 0.001 to 100 parts by weight, preferably 0.0;! To 50 parts by weight, more preferably 0.05 to 30 parts by weight with respect to 1 part by weight of [Component A].
- Parts, [Component C] force SO. 001 to 100 parts by weight, preferably 0.0;! To 50 parts by weight, more preferably 0.05 to 30 parts by weight.
- [Component D] is 0.00;! To 100 parts by weight, preferably 0.01 to; 100 parts by weight, more preferably 0.05 to 30 parts by weight.
- the herbicidal composition of the present invention includes a force S that contains an additive component usually used in an agrochemical formulation as necessary.
- the additive component examples include a carrier such as a solid carrier or a liquid carrier, a surfactant, a binder, a tackifier, a thickener, a colorant, a spreading agent, a spreading agent, an antifreezing agent, an anti-caking agent, Examples include disintegrants and decomposition inhibitors.
- preservatives, plant pieces and the like may be used as additive components, and these additive components may be used alone or in combination of two or more.
- solid carriers include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, tark, bentonite, acid clay, attapulgite, zeolite, diatomaceous earth, etc .; calcium carbonate, ammonium sulfate, sodium sulfate, potassium chloride, etc.
- liquid carrier examples include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, glycerin, and the like.
- the surfactant is not particularly limited! /, But preferably exhibits the ability to gel in water or swell.
- sorbitan fatty acid ester polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl Ether, polyoxyethylene diolenoquineno phenenole etherenole, polyoxyethylene anoleno quineno phenino reater, formalin condensate, polyoxyethylene polyoxypropylene block polymer, anolequinole polyoxypropylene block polymer ethereno, poly Chichetylene alkylamines, polyoxyethylene fatty acid amides, polyoxyethylene fatty acid bisphenylenoate, polyanoleic Benzeno-Reno-Eno-Rye Tenole, Polyoxynoalkyl
- binders and tackifiers include carboxymethylcellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polybulphine redidone, gum arabic, polybulal alcohol, polybutylacetate, poly (polyacetate).
- examples thereof include sodium acrylate, polyethylene glycolol having an average molecular weight of 6,000 to 20,000, polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, natural phospholipids (for example, cefalic acid, lecithin and the like).
- Examples of the thickener include water-soluble polymers such as xanthan gum, guar gum, carboxymethyl cellulose, polybutylpyrrolidone, carboxybutyl polymer, acrylic polymer, starch derivative, polysaccharide; high-purity bentonite, Inorganic fine powder such as white carbon.
- water-soluble polymers such as xanthan gum, guar gum, carboxymethyl cellulose, polybutylpyrrolidone, carboxybutyl polymer, acrylic polymer, starch derivative, polysaccharide; high-purity bentonite, Inorganic fine powder such as white carbon.
- the colorant examples include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue; organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes.
- organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes.
- Examples of the spreading agent include various surfactants such as sodium dialkylsulfosuccinate, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene fatty acid ester, norafine, terpene, polyamide resin, Examples thereof include polyacrylate, polyoxyethylene, wax, polyalkyl alkyl ether, alkylphenol formalin condensate, and synthetic resin emulsion.
- Examples of the antifreezing agent include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
- anti-caking agent examples include polysaccharides such as starch, alginic acid, mannose, and galactose, polybulurpyrrolidone, white carbon, ester gum, and petroleum resin.
- Disintegrants include, for example, sodium tripolyphosphate, sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylic acid ester copolymer, polybutylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene 'isobutylene' anhydrous Examples include maleic acid copolymer and starch 'polyacrylonitrile graft copolymer.
- Examples of the decomposition inhibitor include desiccants such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenol, amine, sulfur, and phosphate; ultraviolet rays such as salicylic acid and benzophenone. An absorbent etc. are mentioned.
- preservative examples include potassium sorbate, 1,2-benzthiazoline 1-3-one, and the like.
- plant pieces examples include sawdust, palm, corn cob, tobacco stem and the like.
- the content ratio is usually 5 to 95%, preferably 20 to 90% for the carrier and usually 0 for the surfactant on the weight basis.
- 1% to 30%, preferably 0.5 to 10%, and other additives are usually selected in the range of 0.5 ;! to 30%, preferably 0.5 to 10%.
- the herbicidal composition of the present invention may be any solution, emulsion, wettable powder, powder, oil, granule wettable powder, floor violet, milk suspension, granule, jumbo drug, sausage emulsion, etc. It is formulated into a dosage form of and used. At the time of formulation, with at least one other pesticide, such as other herbicides, herbicidal microorganisms (Drechslera monoceras, Xanthomonas campestns v. Poae, etc.), insecticides, fungicides, plant growth regulators, fertilizers, etc. It can also be set as a mixed composition.
- bactericidal compounds that can be mixed or used together are exemplified below.
- insecticide compound which can be mixed or used together is illustrated below.
- Metonorecanolev (metolcarb), Mevinphos, monocrotophos, lambda—cyhalothrin, linaxypyr, lufenuron, resmethrin, resmethrin, lepimectin ), Roanone, CL900167, cryolite, DCIP, EPN, MEP, pyrifluquinazon, RU15525, spinetoram, XMC, ZXI8901.
- active ingredients may be used directly, or a composition containing the desired active ingredient is formulated, or each active ingredient is formulated and then mixed. May be.
- each active ingredient of the composition of the present invention may be applied separately or simultaneously.
- the composition of the present invention can be used by diluting with a liquid such as water or fertilizer, or adhering to or spraying on a solid fertilizer, a carrier such as sand or soil, a plant seed, or a tuber. As an application scene, it can be applied to places where weeds will be generated in the future and to the plants themselves.
- the herbicidal composition of the present invention is a variety of weeds that are problematic in fields, non-tillage cultivated land, or non-agricultural land such as roads, parks, slopes, gardens, and forests, such as Broad-leafed weeds, such as sorghum, suzumata katabira, johnsongrass, suzumenotetsupo, wild genital grasses, grasshoppers, aobu, shiroza, chickweed, ichibi, kingfisher deer, staghorn, ragweed, morning glory, etc. It exhibits excellent herbicidal effect at low doses over a wide range of growth periods from perennial and annual perennial weeds such as hamasuge, yellow-headed geese, yellow tag, cricket, and white-eared cricket.
- Broad-leafed weeds such as sorghum, suzumata katabira, johnsongrass, suzumenotetsupo, wild genital grasses, grass
- the major weeds in the field such as buckwheat, Sanaetade, Suberuhi, Shiroza, Aogateto, Noharagarashi, Amanosanemu, Yebisudasa, Ichibi, American kingfish force, American morning glory, Malva asagao, Crested morning glory, Dicotyledonous plants such as cypresses, red fir tree, castor tree, cypress cypress, diptera, cinnamon dungosa, ragweed, etc. It can be effectively weeded.
- the herbicidal composition of the present invention is a rice, wheat, barley, corn, grain sorghum, soybean, soybean, sugar beet, rapeseed, sugarcane, turf, tea, which is highly safe for useful crops and plants. It can be used for useful crops and plants such as fruit trees, vegetables, flowers, and trees.
- the useful crops and useful plants mentioned here are transformed by genetic techniques and are resistant to herbicides, pests, diseases, etc.
- the total amount of [Component A] and [Component B] or the total amount of [Component A], [Component B] and [Component C] is preferably 0.5 to 90. It is preferred to apply in formulations containing% by weight, more preferably;
- the power of the composition of the present invention which can be applied as it is Emulsions, wettable powders, suspensions and the like are applied after diluting a predetermined amount thereof with usually 10 to 2000 liters of water per hectare.
- the application amount of the composition of the present invention may vary depending on the mixing ratio, weather conditions, formulation form, application time, application method, application location, weeds to be controlled, target crops, [Component A] and [Component B] or [Component A], [Component B] and [Component C] are preferably in total amount from 1 lg per lha (hexa); 10,000 g, preferably 5 g to 4000 g, more preferably 10 g ; OOOg is preferred.
- the following components are mixed, and the resulting mixture is pulverized to obtain a wettable powder.
- the following ingredients are mixed, kneaded and granulated.
- the obtained granular material is dried with a fluid bed dryer to obtain a granulated wettable powder.
- 3-0054 represents Compound No. 3-0054.
- TRZAW Italian ryegrass
- LMU Hakobe
- STME Hakobe
- Shiroza C
- the wettable powder prepared according to Formulation Example 1 was weighed so that the active ingredient would be a predetermined amount, diluted with water, and evenly sprayed on the soil surface using a sprayer with a spraying water volume of 200 liters per hectare. . Thereafter, the herbicidal effect and phytotoxicity were investigated on the 60th day of treatment according to the criteria in Table 15. The results are shown in Table 20.
- IBUBI seeds were sown and covered with soil.
- the wettable powder prepared according to Formulation Example 1 is weighed so that the effective component becomes a predetermined amount, diluted with water, and sprayed at 500 liters per hectare. A small sprayer was used to spread evenly on the soil surface. Then, it was grown in a greenhouse and the herbicidal effect and phytotoxicity were investigated according to the criteria in Table 15 on the 21st day of treatment. The results are shown in Table 21.
- a field pot was filled with 11 cm plastic pots of length, width and depth, and seeds of corn (ZEAMX) were sown and covered.
- Various wettable powders prepared according to Formulation Example 1 are weighed so that the active ingredient is in the prescribed amount, diluted with water, and evenly applied to the soil surface using a small sprayer with a spraying amount of 500 liters per hectare. Scattered.
- the plants were then grown in the greenhouse and examined for phytotoxicity on corn according to the criteria in Table 15 on the 21st day of treatment. The results are shown in Table 22.
- the herbicidal composition of the present invention is a variety of weeds that are problematic in paddy fields, upland fields, non-agricultural fields, etc., which are highly safe for useful crops! Can be controlled over a range.
- the entire contents of the specification, claims and abstract of Japanese Patent Application No. 2006-344409 filed on December 21, 2006 are hereby incorporated by reference. It is something that is incorporated.
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Abstract
Description
Claims
Priority Applications (38)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA2671150A CA2671150C (en) | 2006-12-21 | 2007-12-20 | Herbicidal composition comprising an isoxazoline derivative and an additional herbicide |
EP07850994.0A EP2123158B1 (en) | 2006-12-21 | 2007-12-20 | Herbicide composition |
BR122016000025A BR122016000025B1 (pt) | 2006-12-21 | 2007-12-20 | composição herbicida e métodos para preparar a referida composição herbicida e para controlar plantas indesejadas |
BR122016000032A BR122016000032B1 (pt) | 2006-12-21 | 2007-12-20 | composição herbicida e métodos para preparar a referida composição herbicida e para controlar plantas indesejadas |
BR122016000061A BR122016000061B1 (pt) | 2006-12-21 | 2007-12-20 | composição herbicida e métodos para preparar a referida composição herbicida e para controlar plantas indesejadas |
BR122016000063A BR122016000063B1 (pt) | 2006-12-21 | 2007-12-20 | composição herbicida e métodos para preparar a referida composição herbicida e para controlar plantas indesejadas |
UAA200906366A UA97383C2 (ru) | 2006-12-21 | 2007-12-20 | Гербицидные композиции, способ получения и способ борьбы с нежелательными растениями |
EA200970599A EA017352B1 (ru) | 2006-12-21 | 2007-12-20 | Гербицидная композиция |
BR122016000030A BR122016000030B1 (pt) | 2006-12-21 | 2007-12-20 | composição herbicida e métodos para preparar a referida composição herbicida e para controlar plantas indesejadas |
BR122016000042A BR122016000042B1 (pt) | 2006-12-21 | 2007-12-20 | composição herbicida e métodos para preparar a referida composição herbicida e para controlar plantas indesejadas |
BR122016000027A BR122016000027B1 (pt) | 2006-12-21 | 2007-12-20 | composição herbicida e métodos para preparar a referida composição herbicida e para controlar plantas indesejadas |
BR122016000051A BR122016000051B1 (pt) | 2006-12-21 | 2007-12-20 | composição herbicida e métodos para preparar a referida composição herbicida e para controlar plantas indesejadas |
BR122016000031A BR122016000031B1 (pt) | 2006-12-21 | 2007-12-20 | composição herbicida e métodos para preparar a referida composição herbicida e para controlar plantas indesejadas |
SI200731714T SI2123158T1 (sl) | 2006-12-21 | 2007-12-20 | Herbicidni sestavek |
BR122016000071A BR122016000071B1 (pt) | 2006-12-21 | 2007-12-20 | composição herbicida e métodos para preparar a referida composição herbicida e para controlar plantas indesejadas |
JP2008550184A JP5322656B2 (ja) | 2006-12-21 | 2007-12-20 | 除草剤組成物 |
RS20150765A RS54441B1 (en) | 2006-12-21 | 2007-12-20 | HERBICIDE COMPOSITION |
CN200780046590XA CN101562976B (zh) | 2006-12-21 | 2007-12-20 | 除草剂组合物 |
BR122016000076A BR122016000076B1 (pt) | 2006-12-21 | 2007-12-20 | composição herbicida e métodos para preparar a referida composição herbicida e para controlar plantas indesejadas |
NZ576518A NZ576518A (en) | 2006-12-21 | 2007-12-20 | Herbicide composition comprising isoxazoline derivatives |
ES07850994.0T ES2550224T3 (es) | 2006-12-21 | 2007-12-20 | Composición herbicida |
BR122016000062A BR122016000062B1 (pt) | 2006-12-21 | 2007-12-20 | composição herbicida e métodos para preparar a referida composição herbicida e para controlar plantas indesejadas |
MX2009006890A MX2009006890A (es) | 2006-12-21 | 2007-12-20 | Composicion herbicida. |
BR122016000028A BR122016000028B1 (pt) | 2006-12-21 | 2007-12-20 | composição herbicida e métodos para preparar a referida composição herbicida e para controlar plantas indesejadas |
BR122016000044A BR122016000044B1 (pt) | 2006-12-21 | 2007-12-20 | composição herbicida e métodos para preparar a referida composição herbicida e para controlar plantas indesejadas |
PL07850994T PL2123158T3 (pl) | 2006-12-21 | 2007-12-20 | Kompozycja chwastobójcza |
BR122016000068A BR122016000068B1 (pt) | 2006-12-21 | 2007-12-20 | composição herbicida e métodos para preparar a referida composição herbicida e para controlar plantas indesejadas |
BR122016000046A BR122016000046B1 (pt) | 2006-12-21 | 2007-12-20 | composição herbicida e métodos para preparar a referida composição herbicida e para controlar plantas indesejadas |
DK07850994.0T DK2123158T3 (en) | 2006-12-21 | 2007-12-20 | herbicidal |
AU2007335387A AU2007335387B2 (en) | 2006-12-21 | 2007-12-20 | Herbicide composition |
BRPI0721047A BRPI0721047B1 (pt) | 2006-12-21 | 2007-12-20 | composição herbicida e métodos para preparar a referida composição herbicida e para controlar plantas indesejadas |
BR122016000023A BR122016000023B1 (pt) | 2006-12-21 | 2007-12-20 | composição herbicida e métodos para preparar a referida composição herbicida e para controlar plantas indesejadas |
BR122016000040A BR122016000040B1 (pt) | 2006-12-21 | 2007-12-20 | composição herbicida e métodos para preparar a referida composição herbicida e para controlar plantas indesejadas |
BR122016000073A BR122016000073B1 (pt) | 2006-12-21 | 2007-12-20 | composição herbicida e métodos para preparar a referida composição herbicida e para controlar plantas indesejadas |
IL199110A IL199110A (en) | 2006-12-21 | 2009-06-02 | An herbicide containing isoxazole derivative |
EC2009009437A ECSP099437A (es) | 2006-12-21 | 2009-06-17 | Composición herbicida |
AU2010100642A AU2010100642A4 (en) | 2006-12-21 | 2010-06-21 | Herbicidal composition |
HRP20151113TT HRP20151113T1 (en) | 2006-12-21 | 2015-10-22 | Herbicide composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP2006344409 | 2006-12-21 | ||
JP2006-344409 | 2006-12-21 |
Publications (1)
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WO2008075743A1 true WO2008075743A1 (ja) | 2008-06-26 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/JP2007/074569 WO2008075743A1 (ja) | 2006-12-21 | 2007-12-20 | 除草剤組成物 |
Country Status (29)
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US (2) | US8110530B2 (ja) |
EP (1) | EP2123158B1 (ja) |
JP (1) | JP5322656B2 (ja) |
KR (1) | KR101469137B1 (ja) |
CN (8) | CN103250708B (ja) |
AR (1) | AR064606A1 (ja) |
AU (2) | AU2007335387B2 (ja) |
BR (20) | BR122016000030B1 (ja) |
CA (2) | CA2671150C (ja) |
CL (8) | CL2007003725A1 (ja) |
CO (1) | CO6220878A2 (ja) |
CR (1) | CR10876A (ja) |
CY (1) | CY1116813T1 (ja) |
DK (1) | DK2123158T3 (ja) |
EA (7) | EA021235B1 (ja) |
EC (1) | ECSP099437A (ja) |
ES (1) | ES2550224T3 (ja) |
HR (1) | HRP20151113T1 (ja) |
HU (1) | HUE026078T2 (ja) |
IL (1) | IL199110A (ja) |
IN (1) | IN2009DN04070A (ja) |
MX (1) | MX2009006890A (ja) |
NZ (7) | NZ598103A (ja) |
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