JP2023500189A - Herbicidal composition containing N-(1,3,4-oxadiazol-2-yl)arylformamide compound and use thereof - Google Patents
Herbicidal composition containing N-(1,3,4-oxadiazol-2-yl)arylformamide compound and use thereof Download PDFInfo
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- JP2023500189A JP2023500189A JP2022520325A JP2022520325A JP2023500189A JP 2023500189 A JP2023500189 A JP 2023500189A JP 2022520325 A JP2022520325 A JP 2022520325A JP 2022520325 A JP2022520325 A JP 2022520325A JP 2023500189 A JP2023500189 A JP 2023500189A
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- methyl
- herbicidal composition
- ethyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 54
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 40
- 150000001875 compounds Chemical class 0.000 title claims description 59
- 241000196324 Embryophyta Species 0.000 claims abstract description 54
- 239000003112 inhibitor Substances 0.000 claims abstract description 36
- 239000004480 active ingredient Substances 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 150000002148 esters Chemical class 0.000 claims abstract description 10
- 102000029749 Microtubule Human genes 0.000 claims abstract description 5
- 108091022875 Microtubule Proteins 0.000 claims abstract description 5
- 210000004688 microtubule Anatomy 0.000 claims abstract description 5
- AJPADPZSRRUGHI-RFZPGFLSSA-N 1-deoxy-D-xylulose 5-phosphate Chemical compound CC(=O)[C@@H](O)[C@H](O)COP(O)(O)=O AJPADPZSRRUGHI-RFZPGFLSSA-N 0.000 claims abstract description 3
- 101100339555 Zymoseptoria tritici HPPD gene Proteins 0.000 claims abstract description 3
- -1 benzovicilone Chemical compound 0.000 claims description 144
- 239000012053 oil suspension Substances 0.000 claims description 58
- 239000000725 suspension Substances 0.000 claims description 15
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 12
- 239000005574 MCPA Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 239000005562 Glyphosate Substances 0.000 claims description 10
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 claims description 9
- 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 9
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 claims description 8
- ZBMRKNMTMPPMMK-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid;azane Chemical compound [NH4+].CP(O)(=O)CCC(N)C([O-])=O ZBMRKNMTMPPMMK-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- NXQDBZGWYSEGFL-UHFFFAOYSA-N Anilofos Chemical compound COP(=S)(OC)SCC(=O)N(C(C)C)C1=CC=C(Cl)C=C1 NXQDBZGWYSEGFL-UHFFFAOYSA-N 0.000 claims description 8
- 239000005499 Clomazone Substances 0.000 claims description 8
- 239000005578 Mesotrione Substances 0.000 claims description 8
- CHNUNORXWHYHNE-UHFFFAOYSA-N Oxadiazon Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(OC(=N2)C(C)(C)C)=O)=C1Cl CHNUNORXWHYHNE-UHFFFAOYSA-N 0.000 claims description 8
- SYJGKVOENHZYMQ-UHFFFAOYSA-N Penoxsulam Chemical compound N1=C2C(OC)=CN=C(OC)N2N=C1NS(=O)(=O)C1=C(OCC(F)F)C=CC=C1C(F)(F)F SYJGKVOENHZYMQ-UHFFFAOYSA-N 0.000 claims description 8
- YLPGTOIOYRQOHV-UHFFFAOYSA-N Pretilachlor Chemical compound CCCOCCN(C(=O)CCl)C1=C(CC)C=CC=C1CC YLPGTOIOYRQOHV-UHFFFAOYSA-N 0.000 claims description 8
- BGNQYGRXEXDAIQ-UHFFFAOYSA-N Pyrazosulfuron-ethyl Chemical group C1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OCC BGNQYGRXEXDAIQ-UHFFFAOYSA-N 0.000 claims description 8
- NWBFHIJKEYFVND-UHFFFAOYSA-N [4-[2-chloro-4-methylsulfonyl-3-(2,2,2-trifluoroethoxymethyl)benzoyl]-2-ethylpyrazol-3-yl] 1,3-dimethylpyrazole-4-carboxylate Chemical compound N1(C=C(C(=O)OC=2N(CC)N=CC=2C(=O)C2=C(C(=C(S(=O)(=O)C)C=C2)COCC(F)(F)F)Cl)C(C)=N1)C NWBFHIJKEYFVND-UHFFFAOYSA-N 0.000 claims description 8
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- FUHMZYWBSHTEDZ-UHFFFAOYSA-M bispyribac-sodium Chemical compound [Na+].COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C([O-])=O)=N1 FUHMZYWBSHTEDZ-UHFFFAOYSA-M 0.000 claims description 8
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 claims description 8
- SILSDTWXNBZOGF-JWGBMQLESA-N clethodim Chemical compound CCSC(C)CC1CC(O)=C(C(CC)=NOC\C=C\Cl)C(=O)C1 SILSDTWXNBZOGF-JWGBMQLESA-N 0.000 claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 8
- OYIKARCXOQLFHF-UHFFFAOYSA-N isoxaflutole Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OYIKARCXOQLFHF-UHFFFAOYSA-N 0.000 claims description 8
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 claims description 8
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 claims description 8
- DVOODWOZJVJKQR-UHFFFAOYSA-N 5-tert-butyl-3-(2,4-dichloro-5-prop-2-ynoxyphenyl)-1,3,4-oxadiazol-2-one Chemical group O=C1OC(C(C)(C)C)=NN1C1=CC(OCC#C)=C(Cl)C=C1Cl DVOODWOZJVJKQR-UHFFFAOYSA-N 0.000 claims description 7
- 239000005476 Bentazone Substances 0.000 claims description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 7
- 239000005497 Clethodim Substances 0.000 claims description 7
- 239000005566 Imazamox Substances 0.000 claims description 7
- 239000005571 Isoxaflutole Substances 0.000 claims description 7
- 239000005591 Pendimethalin Substances 0.000 claims description 7
- 239000005592 Penoxsulam Substances 0.000 claims description 7
- CSPPKDPQLUUTND-NBVRZTHBSA-N Sethoxydim Chemical compound CCO\N=C(/CCC)C1=C(O)CC(CC(C)SCC)CC1=O CSPPKDPQLUUTND-NBVRZTHBSA-N 0.000 claims description 7
- 239000005621 Terbuthylazine Substances 0.000 claims description 7
- LALGZGDVRILFNW-UHFFFAOYSA-N [2,5-dimethyl-4-[2-methylsulfonyl-4-(trifluoromethyl)benzoyl]pyrazol-3-yl] 1,3-dimethylpyrazole-4-carboxylate Chemical compound CN1N=C(C(=C1)C(=O)OC1=C(C(=NN1C)C)C(C1=C(C=C(C=C1)C(F)(F)F)S(=O)(=O)C)=O)C LALGZGDVRILFNW-UHFFFAOYSA-N 0.000 claims description 7
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 claims description 7
- 229940097068 glyphosate Drugs 0.000 claims description 7
- 229940088649 isoxaflutole Drugs 0.000 claims description 7
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 claims description 7
- 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 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
- 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 6
- 239000007900 aqueous suspension Substances 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 6
- BWUPSGJXXPATLU-UHFFFAOYSA-N dimepiperate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=O)N1CCCCC1 BWUPSGJXXPATLU-UHFFFAOYSA-N 0.000 claims description 6
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 claims description 6
- COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical group C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 claims description 6
- 238000003786 synthesis reaction Methods 0.000 claims description 6
- AZHZOGYUMMIAOF-UHFFFAOYSA-N trifludimoxazin Chemical compound O=C1N(C)C(=S)N(C)C(=O)N1C(C(=C1)F)=CC2=C1OC(F)(F)C(=O)N2CC#C AZHZOGYUMMIAOF-UHFFFAOYSA-N 0.000 claims description 6
- 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 5
- SPNQRCTZKIBOAX-UHFFFAOYSA-N Butralin Chemical compound CCC(C)NC1=C([N+]([O-])=O)C=C(C(C)(C)C)C=C1[N+]([O-])=O SPNQRCTZKIBOAX-UHFFFAOYSA-N 0.000 claims description 5
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- HBPDKDSFLXWOAE-UHFFFAOYSA-N Tebuthiuron Chemical compound CNC(=O)N(C)C1=NN=C(C(C)(C)C)S1 HBPDKDSFLXWOAE-UHFFFAOYSA-N 0.000 claims description 5
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 claims description 5
- OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical group CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 claims description 5
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- ZCNQYNHDVRPZIH-UHFFFAOYSA-N fluthiacet-methyl Chemical group C1=C(Cl)C(SCC(=O)OC)=CC(N=C2N3CCCCN3C(=O)S2)=C1F ZCNQYNHDVRPZIH-UHFFFAOYSA-N 0.000 claims description 5
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- CLQMBPJKHLGMQK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-UHFFFAOYSA-N 0.000 claims description 4
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- ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 description 1
- FKLQIONHGSFYJY-UHFFFAOYSA-N propan-2-yl 5-[4-bromo-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]-2-chloro-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(C=2C(=C(N(C)N=2)C(F)(F)F)Br)=C1F FKLQIONHGSFYJY-UHFFFAOYSA-N 0.000 description 1
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- ZHYPDEKPSXOZKN-UHFFFAOYSA-N propyl 4-[[2-(4,6-dimethoxypyrimidin-2-yl)oxyphenyl]methylamino]benzoate Chemical group C1=CC(C(=O)OCCC)=CC=C1NCC1=CC=CC=C1OC1=NC(OC)=CC(OC)=N1 ZHYPDEKPSXOZKN-UHFFFAOYSA-N 0.000 description 1
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- FKERUJTUOYLBKB-UHFFFAOYSA-N pyrazoxyfen Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 FKERUJTUOYLBKB-UHFFFAOYSA-N 0.000 description 1
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- BUHNESFUCHPWED-UHFFFAOYSA-N s-[(4-methoxyphenyl)methyl] n,n-diethylcarbamothioate Chemical compound CCN(CC)C(=O)SCC1=CC=C(OC)C=C1 BUHNESFUCHPWED-UHFFFAOYSA-N 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229940010115 simetone Drugs 0.000 description 1
- RTWIRLHWLMNVCC-WQYNNSOESA-M sodium (2S)-2-[[(2S)-2-[[(2S)-2-amino-4-[hydroxy(methyl)phosphoryl]butanoyl]amino]propanoyl]amino]propanoate Chemical compound [Na+].[O-]C(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCP(C)(O)=O RTWIRLHWLMNVCC-WQYNNSOESA-M 0.000 description 1
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- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- RFOHRSIAXQACDB-UHFFFAOYSA-M sodium;2-(2,4-dichlorophenoxy)acetate Chemical compound [Na+].[O-]C(=O)COC1=CC=C(Cl)C=C1Cl RFOHRSIAXQACDB-UHFFFAOYSA-M 0.000 description 1
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- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
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- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- VLCQZHSMCYCDJL-UHFFFAOYSA-N tribenuron methyl Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 VLCQZHSMCYCDJL-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- PIHCREFCPDWIPY-UHFFFAOYSA-N tris[2-(2,4-dichlorophenoxy)ethyl] phosphite Chemical compound ClC1=CC(Cl)=CC=C1OCCOP(OCCOC=1C(=CC(Cl)=CC=1)Cl)OCCOC1=CC=C(Cl)C=C1Cl PIHCREFCPDWIPY-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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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- A01N33/20—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
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- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
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- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
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- 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
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- 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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- 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
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- 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<
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- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
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- 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
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- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
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Abstract
N-(1,3,4-オキサジアゾール-2-イル)アリールカルボキサミド化合物を含む除草用組成物およびその用途が開示される。前記除草用組成物は、有効成分Aおよび有効成分Bを除草有効量で含み、前記有効成分Aは【化1】JPEG2023500189000122.jpg49165またはそれらの塩であり、前記有効成分Bは、以下のHPPD阻害剤、PDS阻害剤、DOXP阻害剤、ALS阻害剤、ACCase阻害剤、PPO阻害剤、PSII阻害剤、微小管集合阻害剤等の1種以上の化合物またはその塩もしくはエステルから選択される。前記組成物は、農地におけるシペルス・ディフォルミス(Cyperus difformis)、シペルス・イリア(Cyperus iria)、シルプス・ジュンコイデス(Scirpus juncoides)等のカヤツリグサ科(cyperaceae)の雑草;エキノクロア・フィロポゴン(Echinochloa phyllopogon)、ディジタリア・サングイナリス(Digitaria sanguinalis)、エキノクロア・クルス-ガリ(Echinochloa crus-galli)、レプトクロア・キネンシス(Leptochloa chinensis)等のイネ科の雑草;およびモノコリア・バジナリス(Monochoria vaginalis)、サジタリア・トリフォリア(Sagittaria trifolia)、ルードヴィヒア・プロストレート(Ludwigia prostrate)、アリスマ・プラントアゴ-アクアティカ(Alisma plantago-aquatica)等の広葉雑草を効果的に防除することができ;かつ下記の利点を有する:広範囲の雑草防除を示し、低用量で用いられ、相乗効果をもたらして耐性雑草を除去することができる。Disclosed are herbicidal compositions comprising N-(1,3,4-oxadiazol-2-yl)arylcarboxamide compounds and uses thereof. The herbicidal composition contains an active ingredient A and an active ingredient B in herbicidally effective amounts, wherein the active ingredient A is [Formula 1] JPEG2023500189000122.jpg49165 or a salt thereof, and the active ingredient B is the following HPPD inhibitor agents, PDS inhibitors, DOXP inhibitors, ALS inhibitors, ACCase inhibitors, PPO inhibitors, PSII inhibitors, microtubule assembly inhibitors, etc. or salts or esters thereof. Said composition can be used in farmland on weeds of the cyperaceae family such as Cyperus difformis, Cyperus iria, Scirpus juncoides; Echinochloa phyllopogon, Digitalia Grass weeds such as Digitaria sanguinalis, Echinochloa crus-galli, Leptochloa chinensis; and Monochoria vaginalis, Sagittaria trifolia, Can effectively control broadleaf weeds such as Ludwigia prostrate, Alisma plantago-aquatica; and has the following advantages: Exhibits broad spectrum weed control; , used at low doses, can produce a synergistic effect to eliminate resistant weeds.
Description
本発明は、殺虫剤の技術分野に属し、特にN-(1,3,4-オキサジアゾール-2-イル)アリールカルボキサミド化合物を含む除草用組成物およびその用途に関する。 The present invention belongs to the technical field of insecticides, and particularly relates to herbicidal compositions containing N-(1,3,4-oxadiazol-2-yl)arylcarboxamide compounds and uses thereof.
雑草の化学的防除は、農地の雑草を防除するための最も経済的かつ効果的な手段であるが、単一の化学除草剤または単一の機能的メカニズムを有する複数の化学除草剤を高用量で長期間継続して使用すると、薬剤に対する雑草の抵抗性および耐性に関連する問題が発生する可能性がある。除草用化合物の十分な錯化または配合は、以下の:広範囲の雑草防除を示し、雑草防除効果を改善させ、かつ薬剤に対する雑草の抵抗性および耐性の発生および発達を遅らせるという利点を達成することができることから、上記の問題を解決するための最も効果的な手段の1つである。例えば、特許CN103596946Aには、N-(1,3,4-オキサジアゾール-2-イル)アリールカルボキサミドおよびその除草剤としての使用が開示されている。しかしながら、安全性が高く、雑草防除スペクトルが広く、かつ相乗効果をもたらして耐性雑草を除去することができる除草用組成物が生産において望まれている。 Chemical weed control is the most economical and effective means of controlling weeds on agricultural land, but high doses of a single chemical herbicide or multiple chemical herbicides with a single functional mechanism are often used. Problems related to weed resistance and tolerance to the pesticides can occur with long-term and continuous use in pesticides. Sufficient complexation or formulation of herbicidal compounds achieves the following advantages: exhibiting broad spectrum weed control, improving weed control efficacy, and delaying the emergence and development of weed resistance and tolerance to chemicals. is one of the most effective means for solving the above problems. For example, patent CN103596946A discloses N-(1,3,4-oxadiazol-2-yl)arylcarboxamides and their use as herbicides. However, there is a desire in production for herbicidal compositions that are safe, have a broad spectrum of weed control, and can provide a synergistic effect to eliminate resistant weeds.
従来技術における上記の既存の問題を解決するために、本発明は、N-(1,3,4-オキサジアゾール-2-イル)アリールカルボキサミド化合物を含む除草用組成物およびその用途を提供する。この組成物は、シペルス・ディフォルミス(Cyperus difformis)、シペルス・イリア(Cyperus iria)、シルプス・ジュンコイデス(Scirpus juncoides)等のカヤツリグサ科(cyperaceae)の雑草;エキノクロア・フィロポゴン(Echinochloa phyllopogon)、ディジタリア・サングイナリス(Digitaria sanguinalis)、エキノクロア・クルス-ガリ(Echinochloa crus-galli)、レプトクロア・キネンシス(Leptochloa chinensis)等のイネ科の雑草;およびモノコリア・バジナリス(Monochoria vaginalis)、サジタリア・トリフォリア(Sagittaria trifolia)、ルードヴィヒア・プロストレート(Ludwigia prostrate)、アリスマ・プラントアゴ-アクアティカ(Alisma plantago-aquatica)等の広葉雑草を効果的に防除することができ;かつ下記の利点を有する:広範囲の雑草防除を示し、低用量で用いられ、相乗効果をもたらして耐性雑草を除去することができる。 In order to solve the above existing problems in the prior art, the present invention provides herbicidal compositions containing N-(1,3,4-oxadiazol-2-yl)arylcarboxamide compounds and uses thereof. . This composition contains weeds of the cyperaceae family such as Cyperus difformis, Cyperus iria, Scirpus juncoides; grass weeds such as Digitaria sanguinalis, Echinochloa crus-galli, Leptochloa chinensis; and Monochoria vaginalis, Sagittaria trifolia, Ludwigia Can effectively control broadleaf weeds such as Ludwigia prostrate, Alisma plantago-aquatica; and has the following advantages: exhibits broad spectrum weed control, low Used in doses, they can produce a synergistic effect to eliminate resistant weeds.
N-(1,3,4-オキサジアゾール-2-イル)アリールカルボキサミド化合物を含む除草用組成物であって、有効成分Aおよび有効成分Bを除草有効量で含み、
前記有効成分Aは
前記有効成分Bは、以下の1種以上の化合物またはその塩もしくはエステルから選択される:
(1)例えば、スルコトリオン(CAS番号:99105-77-8)、メソトリオン(CAS番号:104206-82-8)、トプラメゾン(CAS番号:210631-68-8)、テンボトリオン(CAS番号:335104-84-2)、ビシクロピロン(CAS番号:352010-68-5)、テフリルトリオン(CAS番号:473278-76-1)、ベンゾビシロン(CAS番号:156963-66-5)、ビピラゾン(CAS番号:1622908-18-2)、シピラフルオン(CAS番号:1855929-45-1)、トリピラスルホン(CAS番号:1911613-97-2)、フェンピラゾン(CAS番号:1992017-55-6)、ピラスルホトール(CAS番号:365400-11-9)、ピラゾリネート(CAS番号:58011-68-0)、ベンゾフェナプ(CAS番号:82692-44-2)、トルピラレート(CAS番号:1101132-67-5)、フェンキノトリオン(CAS番号:1342891-70-6)、イソキサフルトール(CAS番号:141112-29-0)、ピラゾキシフェン(CAS番号:71561-11-0)および
(2)例えば、フルロクロリドン(CAS番号:61213-25-0)、フルルタモン(CAS番号:96525-23-4)、ジフルフェニカン(CAS番号:83164-33-4)、ピコリナフェン(CAS番号:137641-05-5)、ベフルブタミド(CAS番号:113614-08-7)、ノルフルラゾン(CAS番号:27314-13-2)およびフルリドン(CAS番号:59756-60-4)から選択されるPDS阻害剤;
(3)例えば、クロマゾン(CAS番号:81777-89-1)およびビクスロゾン(CAS番号:81777-95-9)から選択されるDOXP阻害剤;
(4)例えば、トリベヌロン-メチル(CAS番号:101200-48-0)、チフェンスルフロンメチル(CAS番号:79277-27-3)、ベンスルフロンメチル(CAS番号:83055-99-6)、ピラゾスルフロン-エチル(CAS番号:93697-74-6)、チエンカルバゾン-メチル(CAS番号:317815-83-1)、ハロスルフロンメチル(CAS番号:100784-20-1)、プロピリスルフロン(CAS番号:570415-88-2)、メタゾスルフロン(CAS番号:868680-84-6)、リムスルフロン(CAS番号:122931-48-0)、エトキシスルフロン(CAS番号:126801-58-9)、オルトスルファムロン(CAS番号:213464-77-8)、フルカルバゾン-ナトリウム(CAS番号:181274-17-9)、メソスルフロン-メチル(CAS番号:208465-21-8)、ニコスルフロン(CAS番号:111991-09-4)、フォラムスルフロン(CAS番号:173159-57-4)、フルメツラム(CAS番号:98967-40-9)、トリアファモン(CAS番号:874195-61-6)、ペノキススラム(CAS番号:219714-96-2)、クロランスラム-メチル(CAS番号:147150-35-4)、ピロキススラム(CAS番号:422556-08-9)、イマザモックス(CAS番号:114311-32-9)、イマザピック(CAS番号:104098-48-8)、イマザピル(CAS番号:81334-34-1)、ピリミノバック-メチル(CAS番号:147411-69-6)、フロラスラム(CAS番号:145701-23-1)、ピリフタリド(CAS番号:135186-78-6)、ピリベンゾキシム(CAS番号:168088-61-7)、プロカルバゾンナトリウム(CAS番号:181274-15-7)、イマゼタピル(CAS番号:81335-77-5)、クロルスルフロン(CAS番号:64902-72-3)、シノスルフロン(CAS番号:94593-91-6)、シクロスルファムロン(CAS番号:136849-15-5)、アミドスルフロン(CAS番号:120923-37-7)、トリアスルフロン(CAS番号:82097-50-5)、ヨードスルフロンメチルナトリウム(CAS番号:144550-36-7)、フルピルスルフロン-メチルナトリウム(CAS番号:144740-54-5)、フルセトスルフロン(CAS番号:412928-75-7)、メトスルフロンメチル(CAS番号:74223-64-6)、トリトスルフロン(CAS番号:142469-14-5)、スルホスルフロン(CAS番号:141776-32-1)、イマゾスルフロン(CAS番号:122548-33-8)、ビスピリバック-ナトリウム(CAS番号:125401-92-5)およびメトスラム(CAS番号:139528-85-1)から選択されるALS阻害剤;
(5)例えば、クロジナホップ-プロパルギル(CAS番号:105512-06-9)、ピノキサデン(CAS番号:243973-20-8)、クレトジム(CAS番号:99129-21-2)、セトキシジム(CAS番号:74051-80-2)、キザロホップ-P-メチル(CAS番号:100646-51-3)、トラルコキシジム(CAS番号:87820-88-0)、フルアジホップ-ブチル(CAS番号:69806-50-4)、ハロキシホップ-P-メチル(CAS番号:72619-32-0)、ジクロホップ-メチル(CAS番号:51338-27-3)、フェノキサプロップ-P-エチル(CAS番号:71283-80-2)、シハロホップ-ブチル(CAS番号:122008-85-9)、プロホキシジム(CAS番号:139001-49-3)、メタミホップ(CAS番号:256412-89-2)およびプロパキザホップ(CAS番号:111479-05-1)から選択されるACCase阻害剤;
(6)例えば、オキシフルオルフェン(CAS番号:42874-03-3)、フォメサフェン(CAS番号:72178-02-0)、オキサジアゾン(CAS番号:19666-30-9)、オキサジアルギル(CAS番号:39807-15-3)、スルフェントラゾン(CAS番号:122836-35-5)、ピラクロニル(CAS番号:158353-15-2)、フルミオキサジン(CAS番号:103361-09-7)、ペントキサゾン(CAS番号:110956-75-7)、チアフェナシル(CAS番号:1220411-29-9)、サフルフェナシル(CAS番号:372137-35-4)、ピラフルフェン-エチル(CAS番号:129630-19-9)、カルフェントラゾン-エチル(CAS番号:128639-02-1)、ブタフェナシル(CAS番号:134605-64-4)、エトキシフェン-エチル(CAS番号:131086-42-5)、フルオログリコフェン(CAS番号:77501-60-1)、アシフルオルフェン-ナトリウム(CAS番号:62476-59-9)、トリフルジモキサジン(CAS番号:1258836-72-4)、フルチアセット-メチル(CAS番号:117337-19-6)およびエピリフェナシル(CAS番号:353292-31-6)から選択されるPPO阻害剤;
(7)例えば、アトラジン(CAS番号:1912-24-9)、プロミトリン(CAS番号:7287-19-6)、シメトリン(CAS番号:1014-70-6)、テルブチラジン(CAS番号:5915-41-3)、テルブトリン(CAS番号:886-50-0)、アメトリン(CAS番号:834-12-8)、ジプロペトリン(CAS番号:4147-51-7)、ランバスト(CAS番号:845-52-3)、デスメトリン(CAS番号:1014-69-3)、シマジン(CAS番号:122-34-9)、メトリブジン(CAS番号:21087-64-9)、エチオジン(CAS番号:64529-56-2)、アミカルバゾン(CAS番号:129909-90-6)、メタミトロン(CAS番号:41394-05-2)、シアナジン(CAS番号:21725-46-2)、クロロトルロン(CAS番号:15545-48-9)、イソプロツロン(CAS番号:34123-59-6)、ジウロン(CAS番号:330-54-1)、フルオメツロン(CAS番号:2164-17-2)、リヌロン(CAS番号:330-55-2)、テブチウロン(CAS番号:34014-18-1)、ダイムロン(CAS番号:42609-52-9)、モノリヌロン(CAS番号:1746-81-2)、メトブロムロン(CAS番号:3060-89-7)、ネブロン(CAS番号:555-37-3)、ピリダフォル(CAS番号:40020-01-7)、ヘキサジノン(CAS番号:51235-04-2)、ジメタメトリン(CAS番号:22936-75-0)、トリエタジン(CAS番号:1912-26-1)、ブロマシル(CAS番号:314-40-9)、レナシル(CAS番号:2164-08-1)、テルバシル(CAS番号:5902-51-2)、メタベンズチアズロン(CAS番号:18691-97-9)、シズロン(CAS番号:1982-49-6)、イソウロン(CAS番号:55861-78-4)、メトクスロン(CAS番号:19937-59-8)、クロロクスロン(CAS番号:1982-47-4)、トリフルジモキサジン(CAS番号:1258836-72-4)、シクロピリモレート(CAS番号:499231-24-2)、プロパニル(CAS番号:709-98-8)、ピリデート(CAS番号:55512-33-9)、デスメジファム(CAS番号:13684-56-5)、フェンメジファム(CAS番号:13684-63-4)、ベンタゾン(CAS番号:25057-89-0)、オクタン酸ブロモキシニル(CAS番号:1689-99-2)、ブロモキシニル(CAS番号:1689-84-5)およびイオキシニル(CAS番号:1689-83-4)から選択されるPSII阻害剤;
(8)例えば、トリフルラリン(CAS番号:1582-09-8)、ブトラリン(CAS番号:33629-47-9)、ペンジメタリン(CAS番号:40487-42-1)、ジチオピル(CAS番号:97886-45-8)、エタルフルラリン(CAS番号:55283-68-6)、オリザリン(CAS番号:19044-88-3)、ベンフルラリン(CAS番号:1861-40-1)、チアゾピル(CAS番号:117718-60-2)、プロピザミド(CAS番号:23950-58-5)、ダクタール(CAS番号:1861-32-1)、ブタミホス(CAS番号:36335-67-8)から選択される微小管集合阻害剤;
(9)微小管組織化阻害剤:例えば、カルベタミド(CAS番号:16118-49-3);
(10)例えば、アセトクロール(CAS番号:34256-82-1)、ブタクロール(CAS番号:23184-66-9)、プレチラクロール(CAS番号:51218-49-6)、メトラクロール(CAS番号:51218-45-2)、メフェナセット(CAS番号:73250-68-7)、s-メトラクロール(CAS番号:87392-12-9)、フルフェナセット(CAS番号:142459-58-3)、ナプロパミド(CAS番号:15299-99-7)、ピロキサスルホン(CAS番号:447399-55-5)、アニロホス(CAS番号:64249-01-0)、ジメテナミド(CAS番号:87674-68-8)、フェントラザミド(CAS番号:158237-07-1)、イプフェンカルバゾン(CAS番号:212201-70-2)、カフェントロール(CAS番号:125306-83-4)、ピペロホス(CAS番号:24151-93-7)、プロピソクロール(CAS番号:86763-47-5)、アラクロール(CAS番号:15972-60-8)、メタザクロール(CAS番号:67129-08-2)、プロパクロール(CAS番号:1918-16-7)、ペトキサミド(CAS番号:106700-29-2)、ジメスルファゼット(CAS番号:1215111-77-5)およびフェノキサスルホン(CAS番号:639826-16-7)から選択されるVLCFA阻害剤;
(11)例えば、プロスルホカルブ(CAS番号:52888-80-9)、モリネート(CAS番号:2212-67-1)、ベンチオカルブ(CAS番号:28249-77-6)、ベンフレセート(CAS番号:68505-69-1)、エトフメセート(CAS番号:26225-79-6)、トリアレート(CAS番号:2303-17-5)、ベルノレート(CAS番号:1929-77-7)、ブチレート(CAS番号:2008-41-5)、シクロエート(CAS番号:1134-23-2)、ジメピペレート(CAS番号:61432-55-1)およびエスプロカルブ(CAS番号:85785-20-2)から選択される脂質合成(非アセチルCoAカルボキシラーゼ)阻害剤;
(12)例えば、キンクロラック(CAS番号:84087-01-4)、フルロキシピル(CAS番号:69377-81-7)、フルロキシピルメプチル(CAS番号:81406-37-3)、ハロキシフェン-メチル(CAS番号:943831-98-9)、トリクロピル(CAS番号:55335-06-3)、クロピラリド(CAS番号:1702-17-6)、ピクロラム(CAS番号:1918-02-1)、アミノピラリド(CAS番号:150114-71-9)、ジカンバ(CAS番号:1918-00-9)、フロルピラキシフェンベンジル(CAS番号:1390661-72-9)、MCPA(CAS番号:94-74-6)、MCPA-チオエチル(CAS番号:25319-90-8)、MCPB(CAS番号:94-81-5)、2-(2-メチル-4-クロロフェノキシ)プロピオン酸(CAS番号:93-65-2)、2-(4-クロロ-2-メチルフェノキシ)酢酸ナトリウム(CAS番号:3653-48-3)、(2-メチル-4-クロロフェノキシ)酢酸イソオクチル(CAS番号:26544-20-7)、2,4-ジクロロフェノキシ酢酸ブチル(CAS番号:94-80-4)、2,4-ジクロロフェノキシ酢酸イソオクチル(CAS番号:25168-26-7)、2,4-ジクロロフェノキシ酢酸(CAS番号:94-75-7)、キンメラック(CAS番号:90717-03-6)、MCPAジメチルアンモニウム塩(CAS番号:2039-46-5)、2-(2,4-ジクロロフェノキシル)プロピオン酸(CAS番号:120-36-5)、2,4-ジクロロフェノキシ酪酸(CAS番号:94-82-6)、ベナゾリン-エチル(CAS番号:25059-80-7)、アミノシクロピラクロール(CAS番号:858956-08-8)、
(13)例えば、グリホセート(CAS番号:1071-83-6)およびスルホセート(CAS番号:81591-81-3)から選択されるEPSPS阻害剤;
(14)例えば、グルホシネートアンモニウム(CAS番号:77182-82-2)、ビアラホス(CAS番号:35597-43-4)およびグルホシネート-P-アンモニウム(CAS番号:73777-50-1))から選択されるGS阻害剤;
(15)例えば、パラコート二塩化物(CAS番号:1910-42-5)およびジクワット二臭化物一水和物(CAS番号:6385-62-2)から選択されるPSI阻害剤;
(16)DHP阻害剤:例えば、アスラム(CAS番号:3337-71-1);
(17)例えば、トリアジフラム(CAS番号:131475-57-5)およびインダジフラム(CAS番号:950782-86-2)から選択されるセルロース合成阻害剤;
(18)例えば、オキサジクロメフォン(CAS番号:153197-14-9)、シンメチリン(CAS番号:87818-31-3)、インダノファン(CAS番号:133220-30-1)、ジクロロキノリノン(CAS番号:1350901-36-8)、クイカオトン(CAS番号:1639426-14-4)、クミルロン(CAS番号:99485-76-4)、モヌロン(CAS番号:150-68-5)およびテトフルピロリメット(CAS番号:2053901-33-8)から選択されるその他のもの。
A herbicidal composition comprising an N-(1,3,4-oxadiazol-2-yl)arylcarboxamide compound, comprising active ingredient A and active ingredient B in herbicidally effective amounts,
The active ingredient A is
Said active ingredient B is selected from one or more of the following compounds or salts or esters thereof:
(1) For example, sulcotrione (CAS number: 99105-77-8), mesotrione (CAS number: 104206-82-8), topramezone (CAS number: 210631-68-8), tembotrione (CAS number: 335104-84) -2), bicyclopyrone (CAS number: 352010-68-5), tefuryltrione (CAS number: 473278-76-1), benzovicilone (CAS number: 156963-66-5), bipyrazone (CAS number: 1622908- 18-2), sipirafluon (CAS number: 1855929-45-1), tripyrasulfone (CAS number: 1911613-97-2), fenpyrazone (CAS number: 1992017-55-6), pyrasulfotole (CAS number: 365400-11-9), pyrazolinate (CAS number: 58011-68-0), benzofenap (CAS number: 82692-44-2), tolpiralate (CAS number: 1101132-67-5), fenquinotrione (CAS number : 1342891-70-6), isoxaflutole (CAS number: 141112-29-0), pyrazoxifene (CAS number: 71561-11-0) and
(2) For example, flurochloridone (CAS number: 61213-25-0), flulutamone (CAS number: 96525-23-4), diflufenican (CAS number: 83164-33-4), picolinafen (CAS number: 137641- 05-5), beflubutamide (CAS number: 113614-08-7), norflurazone (CAS number: 27314-13-2) and fluridone (CAS number: 59756-60-4);
(3) DOXP inhibitors selected, for example, from clomazone (CAS number: 81777-89-1) and bixrozone (CAS number: 81777-95-9);
(4) For example, tribenuron-methyl (CAS number: 101200-48-0), thifensulfuron-methyl (CAS number: 79277-27-3), bensulfuron-methyl (CAS number: 83055-99-6), pyrazosulfuron- ethyl (CAS number: 93697-74-6), thiencarbazone-methyl (CAS number: 317815-83-1), halosulfuron methyl (CAS number: 100784-20-1), propyrisulfuron (CAS number: 570415-88 -2), metazosulfuron (CAS number: 868680-84-6), rimsulfuron (CAS number: 122931-48-0), ethoxysulfuron (CAS number: 126801-58-9), orthosulfamuron (CAS number) : 213464-77-8), flucarbazone-sodium (CAS number: 181274-17-9), mesosulfuron-methyl (CAS number: 208465-21-8), nicosulfuron (CAS number: 111991-09-4), forum sulfuron (CAS number: 173159-57-4), flumetsulam (CAS number: 98967-40-9), triafamone (CAS number: 874195-61-6), penoxsulam (CAS number: 219714-96-2), cloransulam -methyl (CAS number: 147150-35-4), piroxsulam (CAS number: 422556-08-9), imazamox (CAS number: 114311-32-9), imazapic (CAS number: 104098-48-8), imazapyr (CAS number: 81334-34-1), pyriminobac-methyl (CAS number: 147411-69-6), florasulam (CAS number: 145701-23-1), pyriftalide (CAS number: 135186-78-6), pyribenzoxime (CAS number: 168088-61-7), procarbazone sodium (CAS number: 181274-15-7), imazethapyr (CAS number: 81335-77-5), chlorsulfuron (CAS number: 64902-72-3) ), cinosulfuron (CAS number: 94593-91-6), cyclosulfamuron (CAS number: 136849-15-5), amidosulfuron (CAS number: 120923-37-7), triasulfuron (CAS number: 82097 -50-5), iodosulfuron methyl sodium (CAS number: 1445 50-36-7), flupyrsulfuron-methyl sodium (CAS number: 144740-54-5), flucetosulfuron (CAS number: 412928-75-7), metsulfuron methyl (CAS number: 74223-64-6) ), tritosulfuron (CAS number: 142469-14-5), sulfosulfuron (CAS number: 141776-32-1), imazosulfuron (CAS number: 122548-33-8), bispyribac-sodium (CAS number: 125401 -92-5) and Methoslam (CAS Number: 139528-85-1);
(5) For example, clodinafop-propargyl (CAS number: 105512-06-9), pinoxaden (CAS number: 243973-20-8), clethodim (CAS number: 99129-21-2), sethoxydim (CAS number: 74051- 80-2), Quizalofop-P-methyl (CAS number: 100646-51-3), Tralkoxydim (CAS number: 87820-88-0), Fluazifop-butyl (CAS number: 69806-50-4), Haloxyfop-P -methyl (CAS number: 72619-32-0), diclofop-methyl (CAS number: 51338-27-3), fenoxaprop-p-ethyl (CAS number: 71283-80-2), cyhalofop-butyl (CAS No.: 122008-85-9), propoxydim (CAS No.: 139001-49-3), metamifop (CAS No.: 256412-89-2) and propaxafop (CAS No.: 111479-05-1) an ACCase inhibitor;
(6) For example, oxyfluorfen (CAS number: 42874-03-3), fomesafen (CAS number: 72178-02-0), oxadiazone (CAS number: 19666-30-9), oxadiargyl (CAS number: 39807-15) -3), sulfentrazone (CAS number: 122836-35-5), pyraclonil (CAS number: 158353-15-2), flumioxazin (CAS number: 103361-09-7), pentoxazone (CAS number: 110956) -75-7), thiaphenacil (CAS number: 1220411-29-9), saflufenacil (CAS number: 372137-35-4), pyraflufen-ethyl (CAS number: 129630-19-9), carfentrazone-ethyl (CAS number: 128639-02-1), butaphenacyl (CAS number: 134605-64-4), ethoxyphene-ethyl (CAS number: 131086-42-5), fluoroglycophene (CAS number: 77501-60-1) ), acifluorfen-sodium (CAS number: 62476-59-9), trifludimoxazine (CAS number: 1258836-72-4), fluthiacet-methyl (CAS number: 117337-19-6) and epirifenacil ( CAS Number: 353292-31-6);
(7) For example, atrazine (CAS number: 1912-24-9), promitrin (CAS number: 7287-19-6), simetryn (CAS number: 1014-70-6), terbuthylazine (CAS number: 5915-41- 3), terbutryn (CAS number: 886-50-0), ametrine (CAS number: 834-12-8), dipropethrin (CAS number: 4147-51-7), lambast (CAS number: 845-52-3) , desmethrin (CAS number: 1014-69-3), simazine (CAS number: 122-34-9), metribuzine (CAS number: 21087-64-9), ethiodine (CAS number: 64529-56-2), amicarbazone (CAS number: 129909-90-6), metamitron (CAS number: 41394-05-2), cyanazine (CAS number: 21725-46-2), chlorotoluron (CAS number: 15545-48-9), isoproturon (CAS number: number: 34123-59-6), diuron (CAS number: 330-54-1), fluometuron (CAS number: 2164-17-2), linuron (CAS number: 330-55-2), tebuthiuron (CAS number: 34014-18-1), Daimuron (CAS Number: 42609-52-9), Monolinuron (CAS Number: 1746-81-2), Metobromuron (CAS Number: 3060-89-7), Nevron (CAS Number: 555- 37-3), pyridafol (CAS number: 40020-01-7), hexazinone (CAS number: 51235-04-2), dimethamethrin (CAS number: 22936-75-0), trietadine (CAS number: 1912-26- 1), bromacil (CAS number: 314-40-9), renacil (CAS number: 2164-08-1), terbacil (CAS number: 5902-51-2), metabenzthiazuron (CAS number: 18691- 97-9), Cizuron (CAS Number: 1982-49-6), Isouron (CAS Number: 55861-78-4), Metoxuron (CAS Number: 19937-59-8), Chloroxuron (CAS Number: 1982-47- 4), trifludimoxazine (CAS number: 1258836-72-4), cyclopyrimolate (CAS number: 499231-24-2), propanyl (CAS number: 709-98-8), pyridate (CAS number: 55512-33-9), desmedifam (CAS number: 13684-56-5), phenmedifam (CAS number: 13684-63-4), bentazone (CAS number: 25057-89-0), bromoxynil octanoate (CAS number: 1689-99-2 ), bromoxynil (CAS number: 1689-84-5) and ioxynil (CAS number: 1689-83-4);
(8) For example, trifluralin (CAS number: 1582-09-8), butralin (CAS number: 33629-47-9), pendimethalin (CAS number: 40487-42-1), dithiopyr (CAS number: 97886-45- 8), ethalfluralin (CAS number: 55283-68-6), oryzalin (CAS number: 19044-88-3), benfluralin (CAS number: 1861-40-1), thiazopir (CAS number: 117718-60- 2) a microtubule assembly inhibitor selected from propyzamide (CAS number: 23950-58-5), Ductal (CAS number: 1861-32-1), butamiphos (CAS number: 36335-67-8);
(9) microtubule assembly inhibitors: such as carbetaamide (CAS number: 16118-49-3);
(10) For example, acetochlor (CAS number: 34256-82-1), butachlor (CAS number: 23184-66-9), pretilachlor (CAS number: 51218-49-6), metolachlor (CAS number: 51218- 45-2), mefenacet (CAS number: 73250-68-7), s-metolachlor (CAS number: 87392-12-9), flufenacet (CAS number: 142459-58-3), napropamide (CAS number : 15299-99-7), pyroxasulfone (CAS number: 447399-55-5), anilophos (CAS number: 64249-01-0), dimethenamide (CAS number: 87674-68-8), fentrazamide (CAS number : 158237-07-1), ipfencarbazone (CAS number: 212201-70-2), caffethrol (CAS number: 125306-83-4), piperophos (CAS number: 24151-93-7), propiso Chlor (CAS number: 86763-47-5), alachlor (CAS number: 15972-60-8), metazachlor (CAS number: 67129-08-2), propachlor (CAS number: 1918-16-7) , petoxamide (CAS number: 106700-29-2), dimesulfazet (CAS number: 1215111-77-5) and phenoxasulfone (CAS number: 639826-16-7);
(11) For example, prosulfocarb (CAS number: 52888-80-9), molinate (CAS number: 2212-67-1), benchocarb (CAS number: 28249-77-6), benfuresate (CAS number: 68505- 69-1), ethofumesate (CAS number: 26225-79-6), trialate (CAS number: 2303-17-5), vernolate (CAS number: 1929-77-7), butyrate (CAS number: 2008- 41-5), cycloate (CAS number: 1134-23-2), dimepiperate (CAS number: 61432-55-1) and esprocarb (CAS number: 85785-20-2) for lipid synthesis (non-acetyl CoA carboxylase) inhibitors;
(12) For example, quinclolac (CAS number: 84087-01-4), fluroxypyr (CAS number: 69377-81-7), fluroxypyrmeptyl (CAS number: 81406-37-3), haloxifene-methyl ( CAS number: 943831-98-9), triclopyr (CAS number: 55335-06-3), clopyralid (CAS number: 1702-17-6), picloram (CAS number: 1918-02-1), aminopyralid (CAS number : 150114-71-9), dicamba (CAS number: 1918-00-9), florpyraxifene benzyl (CAS number: 1390661-72-9), MCPA (CAS number: 94-74-6), MCPA- Thioethyl (CAS number: 25319-90-8), MCPB (CAS number: 94-81-5), 2-(2-methyl-4-chlorophenoxy) propionic acid (CAS number: 93-65-2), 2 -(4-chloro-2-methylphenoxy) sodium acetate (CAS number: 3653-48-3), (2-methyl-4-chlorophenoxy) isooctyl acetate (CAS number: 26544-20-7), 2,4 -butyl dichlorophenoxyacetate (CAS number: 94-80-4), isooctyl 2,4-dichlorophenoxyacetate (CAS number: 25168-26-7), 2,4-dichlorophenoxyacetic acid (CAS number: 94-75- 7), quinmerac (CAS number: 90717-03-6), MCPA dimethylammonium salt (CAS number: 2039-46-5), 2-(2,4-dichlorophenoxyl) propionic acid (CAS number: 120- 36-5), 2,4-dichlorophenoxybutyric acid (CAS number: 94-82-6), benazolin-ethyl (CAS number: 25059-80-7), aminocyclopyrachlor (CAS number: 858956-08-8) ),
(13) EPSPS inhibitors selected, for example, from glyphosate (CAS number: 1071-83-6) and sulfosate (CAS number: 81591-81-3);
(14) selected from, for example, glufosinate-ammonium (CAS number: 77182-82-2), bialaphos (CAS number: 35597-43-4) and glufosinate-P-ammonium (CAS number: 73777-50-1)) GS inhibitor;
(15) PSI inhibitors selected, for example, from paraquat dichloride (CAS number: 1910-42-5) and diquat dibromide monohydrate (CAS number: 6385-62-2);
(16) DHP inhibitors: such as Aslam (CAS Number: 3337-71-1);
(17) cellulose synthesis inhibitors selected, for example, from triaziflam (CAS number: 131475-57-5) and indaziflam (CAS number: 950782-86-2);
(18) For example, oxadiclomefone (CAS number: 153197-14-9), cymmethylin (CAS number: 87818-31-3), indanophan (CAS number: 133220-30-1), dichloroquinolinone (CAS number : 1350901-36-8), cuikaoton (CAS number: 1639426-14-4), cumyluron (CAS number: 99485-76-4), monuron (CAS number: 150-68-5) and tetoflupyrrolimet (CAS No.: 2053901-33-8).
本明細書の文脈において、活性化合物の一般名の略語が用いられる場合、それは、それぞれの場合において、エステルおよび塩等のすべての慣習的な誘導体、ならびに異性体、特に光学異性体、特に1種以上の市販されている形態を含む。一般名がエステルまたは塩を示す場合、それは、それぞれの場合において、他のエステルおよび塩、遊離酸および中性化合物等の他のすべての慣用される誘導体、ならびに異性体、特に光学異性体、特に1種以上の市販されている形態も含む。化合物に付けられた化学名は、一般名に含まれる少なくとも1つの化合物、および一般的に好ましい化合物を意味する。スルホニル尿素等のスルホンアミドの場合、塩には、スルホンアミド基において水素原子との陽イオンとの交換によって形成される塩も含まれる。例えば、2-メチル-4-クロロ誘導体としては、限定されないが、2-メチル-4-クロロナトリウム塩、-カリウム塩、-ジメチルアンモニウム塩、-イソプロピルアミン塩等、ならびに2-メチル-4-クロロメチルエステル、-エチルエステル、-イソオクチルエステル、-チオエチル等が挙げられ;2,4-D誘導体としては、限定されないが、ナトリウム塩、カリウム塩、ジメチルアンモニウム塩、トリエタノールアンモニウム塩、イソプロピルアミン塩、コリン等の2,4-D塩、およびメチルエステル、エチルエステル、ブチルエステル、イソオクチルエステル等の2,4-Dエステルが挙げられる。 In the context of the present specification, when abbreviations of common names of active compounds are used, it means in each case all customary derivatives, such as esters and salts, and isomers, especially optical isomers, especially one Including the commercially available forms of the above. Where a generic name designates an ester or salt, it is in each case other esters and salts, all other customary derivatives such as free acids and neutral compounds, and isomers, especially optical isomers, especially It also includes one or more commercially available forms. A chemical name given to a compound means at least one of the compounds included in the generic name, and generally preferred compounds. In the case of sulfonamides, such as sulfonylureas, salts also include salts formed by exchange of a hydrogen atom with a cation at the sulfonamide group. For example, 2-methyl-4-chloro derivatives include, but are not limited to, 2-methyl-4-chloro sodium salt, -potassium salt, -dimethylammonium salt, -isopropylamine salt and the like, as well as 2-methyl-4-chloro methyl esters, -ethyl esters, -isooctyl esters, -thioethyl and the like; 2,4-D derivatives include, but are not limited to, sodium salts, potassium salts, dimethylammonium salts, triethanolammonium salts, isopropylamine salts. , 2,4-D salts such as choline, and 2,4-D esters such as methyl ester, ethyl ester, butyl ester, isooctyl ester and the like.
いくつかの実施形態において、有効成分Aと有効成分Bとが、1:600~200:1または1:500~100:1、好ましくは1:300~80:1または1:200~60:1、より好ましくは1:150~50:1または1:120~30:1、より一層好ましくは1:100~20:1または1:80~15:1、さらにより一層好ましくは1:50~10:1、1:30~5:1、1:10~4:1または1:5~1:1の重量比である。 In some embodiments, the ratio of active ingredient A to active ingredient B is 1:600-200:1 or 1:500-100:1, preferably 1:300-80:1 or 1:200-60:1. , more preferably 1:150-50:1 or 1:120-30:1, even more preferably 1:100-20:1 or 1:80-15:1, even more preferably 1:50-10 :1, 1:30 to 5:1, 1:10 to 4:1 or 1:5 to 1:1 weight ratio.
特定の実施形態において、本発明はまた、成分Aおよび成分Bの以下の特定の組み合わせを列挙する。
別の特定の実施形態において、上記表の成分Aは、対応する塩で置き換えられている。 In another specific embodiment, component A in the table above is replaced with the corresponding salt.
本発明の文脈において、化合物の塩は、好ましくは、それぞれのアルカリ金属塩、アルカリ土類金属塩またはアンモニウム塩(例えば、ジメチルアミン塩、トリエタノールアミン塩、イソプロピルアミン塩、コリンアミン塩等)の形態であり、好ましくはそれぞれのアルカリ金属塩の形態であり、より好ましくはそれぞれのナトリウムまたはカリウム塩の形態であり、最も好ましくはそれぞれのナトリウム塩の形態である。 In the context of the present invention, the salts of the compounds are preferably in the form of their respective alkali metal, alkaline earth metal or ammonium salts (e.g. dimethylamine salts, triethanolamine salts, isopropylamine salts, cholineamine salts etc.). , preferably in the form of the respective alkali metal salts, more preferably in the form of the respective sodium or potassium salts, most preferably in the form of the respective sodium salts.
いくつかの実施形態において、有効成分AおよびBは、合計で、除草用組成物の総重量の1~95%、好ましくは10~80%を占める。 In some embodiments, active ingredients A and B together constitute 1-95%, preferably 10-80%, of the total weight of the herbicidal composition.
除草用組成物は、慣用されるアジュバントを含み得、慣用されるアジュバントは、例えば、担体および/または界面活性剤を含む。 Herbicidal compositions may contain conventional adjuvants, which include, for example, carriers and/or surfactants.
本明細書における「担体」という用語は、有効成分の適用を容易にする有機または無機、天然または合成の物質を指す。一般に、担体は不活性であり、農業的に許容可能でなければならず、特に処理される植物において許容可能でなければならない。担体は、粘土、天然または合成ケイ酸塩、シリカ、樹脂、ワックス、固体肥料等の固体;または、水、アルコール、ケトン、石油留分、芳香族系またはパラフィン系炭化水素、クロロ炭化水素、液化ガス等の液体であり得る。 The term "carrier" as used herein refers to an organic or inorganic substance, natural or synthetic, that facilitates the application of the active ingredient. In general, the carrier should be inert and agriculturally acceptable, especially in the plants being treated. Carriers can be solids such as clays, natural or synthetic silicates, silica, resins, waxes, solid fertilizers; or water, alcohols, ketones, petroleum fractions, aromatic or paraffinic hydrocarbons, chlorohydrocarbons, liquefied It can be a liquid such as a gas.
イオン性または非イオン性であり得る界面活性剤は、乳化剤、分散剤または湿潤剤を含むことができる。言及され得る例は、ポリアクリル酸の塩、リグノスルホン酸の塩、フェノールスルホン酸またはナフタレンスルホン酸の塩、脂肪族アルコールまたは脂肪酸または脂肪族アミンまたは置換フェノール(特に、アルキルフェノールまたはアリールフェノール)とエチレンオキシドとの重合体、スルホコハク酸塩、タウリン誘導体(特にタウリン酸アルキル)、およびアルコールまたはポリヒドロキシエチル化フェノールのリン酸エステル、スルホン酸アルキル、スルホン酸アルキルアリール、硫酸アルキル、ラウリルエーテル硫酸塩、脂肪アルコール硫酸塩、硫酸化されたヘキサデカノール、ヘプタデカノールおよびオクタデカノール、および硫酸化された脂肪アルコールポリグリコールエーテルであり得、さらに、ナフタレンまたはナフタレンスルホン酸とフェノールおよびホルムアルデヒド、ポリオキシエチレンオクチルフェニルエーテル、エトキシル化イソオクチルフェノール、オクチルフェノールまたはノニルフェノールとの縮合物、ポリエチレングリコールアルキルフェニルエーテル、ポリエチレングリコールトリブチルフェニルエーテル、ポリエチレングリコールトリステアリルフェニルエーテル、アルキルアリールポリエーテルアルコール、アルコールおよび脂肪アルコール/エチレンオキシド縮合物、エトキシル化ヒマシ油、ポリオキシエチレンアルキルエーテル、エトキシル化ポリオキシプロピレン、ラウリルアルコールポリグリコールエーテルアセタール、ソルビトールエステル、リグニンサルファイト廃液、タンパク質、変性タンパク質、多糖類(例えば、メチルセルロース)、疎水性修飾デンプン、ポリビニルアルコール、ポリカルボキシレート、ポリアルコキシレート、ポリビニルアミン、ポリビニルピロリドン、およびそれらのコポリマーが挙げられる。有効成分の水中への分散および植物への適切な適用を容易にするために、少なくとも1つの界面活性剤が必要とされ得る。 Surfactants, which may be ionic or nonionic, may include emulsifying agents, dispersing agents or wetting agents. Examples which may be mentioned are salts of polyacrylic acids, salts of lignosulfonic acids, salts of phenolsulfonic acids or naphthalenesulfonic acids, fatty alcohols or fatty acids or fatty amines or substituted phenols (especially alkylphenols or arylphenols) and ethylene oxide. sulfosuccinates, taurine derivatives (especially alkyl taurates), and phosphate esters of alcohols or polyhydroxyethylated phenols, alkyl sulfonates, alkylaryl sulfonates, alkyl sulfates, lauryl ether sulfates, fatty alcohols sulfates, sulfated hexadecanol, heptadecanol and octadecanol, and sulfated fatty alcohol polyglycol ethers, and also naphthalene or naphthalenesulfonic acids with phenols and formaldehyde, polyoxyethylene octylphenyl Condensates with ethers, ethoxylated isooctylphenols, octylphenols or nonylphenols, polyethylene glycol alkylphenyl ethers, polyethylene glycol tributylphenyl ethers, polyethylene glycol tristearylphenyl ethers, alkylaryl polyether alcohols, alcohol and fatty alcohol/ethylene oxide condensates, ethoxyl castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol ester, lignin sulfite waste liquid, protein, denatured protein, polysaccharides (e.g. methylcellulose), hydrophobically modified starch, polyvinyl Alcohols, polycarboxylates, polyalkoxylates, polyvinylamines, polyvinylpyrrolidone, and copolymers thereof. At least one surfactant may be required to facilitate dispersion of the active ingredient in water and proper application to the plant.
組成物はまた、保護コロイド、接着剤、増粘剤、チキソトロピー剤、浸透剤、安定剤、キレート剤、染料、着色剤またはポリマー等の様々な他の成分を含むことができる。 The compositions can also include various other ingredients such as protective colloids, adhesives, thickeners, thixotropic agents, penetrants, stabilizers, chelating agents, dyes, colorants or polymers.
さらに、例えば、活性化合物と組み合わせることができる組成物は、例えば、World Herbicide New Product Technology Handbook, China Agricultural Science and Farming Techniques Press, 2010.9およびそこに引用されている文献に記載されている既知の活性化合物である。例えば、以下の活性化合物が除草剤として言及される場合がある(注:これらの化合物は、国際標準化機構(ISO)に従って「一般名」で命名されるか、適切な場合は通常のコード番号とともに化学名で命名される。):アセトクロール、ブタクロール、アラクロール、プロピソクロール、メトラクロール、s-メトラクロール、プレチラクロール、プロパクロール、エタクロール、ナプロパミド、R-左回り(R-left handed)ナプロパミド、プロパニル、メフェナセット、ジフェナミド、ジフルフェニカン、エタプロクロール、ベフルブタミド、ブロモブチド、ジメテナミド、ジメテナミド-P、エトベンザニド、フルフェナセット、テニルクロール、メタザクロール、イソキサベン、フラムプロップ-M-メチル、フラムプロップ-M-プロピル、アリドクロール、ペトキサミド、クロラノクリル、シプラジン、メフルイジド、モナリド、デラクロール、プリナクロール、テルブクロール、キシラクロール、ジメタクロール、シサニリド、トリメキサクロール、クロメプロップ、プロピザミド、ペンタノクロール、カルベタミド、ベンゾイルプロプ-エチル、シプラゾール、ブテナクロール、テブタム、ベンジプラム、モグルトン、ジクロフルアニド、ナプロアニリド、ジエタチル-エチル、ナプタラム、フルフエナセット、ベンザドックス、クロルチアミド、クロロフタルイミド、イソカルバミド、ピコリナフェン、アトラジン、シマジン、プロメトリン、シアナトリン、シメトリン、アメトリン、プロパジン、ジプロペトリン、SSH-108、テルブトリン、テルブチラジン、トリアジフラム、シプラジン、プログリナジン、トリエタジン、プロメトン、シメトン、アジプロトリン、デスメトリン、ジメタメトリン、プロシアジン、メソプラジン、セブチラジン、セクブメトン、テルブメトン、メトプロトリン、シアナトリン、イパジン、クロラジン、アトラトン、ペンジメタリン、エグ
リナジン、シアヌル酸、インダジフラム、クロルスルフロン、メトスルフロン-メチル、ベンスルフロンメチル、クロリムロン-エチル、トリベヌロン-メチル、チフェンスルフロン-メチル、ピラゾスルフロン-エチル、メソスルフロン、ヨードスルフロン-メチルナトリウム、ホラムスルフロン、シノスルフロン、トリアスルフロン、スルホメツロンメチル、ニコスルフロン、エタメトスルフロン-メチル、アミドスルフロン、エトキシスルフロン、シクロスルファムロン、リムスルフロン、アジムスルフロン、フラザスルフロン、モノスルフロン、モノスルフロン-エステル、フルカルバゾン-ナトリウム、フルピルスルフロン-メチル、ハロスルフロン-メチル、オキサスルフロン、イマゾスルフロン、プリミスルフロン、プロポキシカルバゾン、プロスルフロン、スルホスルフロン、トリフロキシスルフロン、トリフルスルフロン-メチル、トリトスルフロン、メトスルフロンメチルナトリウム、フルセトスルフロン、HNPC-C、オルトスルファムロン、プロピリスルフロン、メタゾスルフロン、アシフルオルフェン、ホメサフェン、ラクトフェン、フルオログリコフェン、オキシフルオルフェン、クロルニトロフェン、アクロニフェン、エトキシフェン-エチル、ビフェノックス、ニトロフルオルフェン、クロメトキシフェン、フルオロジフェン、フルオロニトロフェン、フリロキシフェン、ニトロフェン、TOPE、DMNP、PPG1013、AKH-7088、ハロサフェン、クロルトルロン、イソプロツロン、リヌロン、ジウロン、ダイムロン、フルオメツロン、ベンズチアズロン、メタベンズチアズロン、クミルロン、エチジムロン、イソウロン、テブチウロン、ブツロン、クロルブロムロン、メチルダイムロン、フェノベンズロン、SK-85、メトブロムロン、メトクスロン、モノリヌロン、モヌロン、シズロン、フェヌロン、フルオチウロン、ネブロン、クロロクスロン、ノルロン、イソノルロン、3-シクロオクチル-1、チアズフルロン、テブチウロン、ジフェノクスロン、パラフルロン、メチルアミン、トリブニル、カルブチレート、トリメツロン、ジメフロン、モニソウロン、アニスロン、メチウロン、クロレツロン、テトラフルロン、フェンメジファム、フェンメジファム-エチル、デスメジファム、アスラム、テルブカルブ、バルバン、プロファム、クロルプロファム、ロウメート、スウェップ、クロルブファム、カルボキサゾール、クロルプロカルブ、フェナスラム、BCPC、CPPC、カルバスラム、ブチレート、ベンチオカルブ、ベルノレート、モリネート、トリアレート、ジメピペレート、エスプロカルブ、ピリブチカルブ、シクロエート、アバデックス、EPTC、エチオレート、オルベンカルブ、ペブレート、プロスルホカルブ、チオカルバジル、CDEC、ジメキサノ、イソポリネート、メチオベンカルブ、2,4-Dブチルエステル、MCPA-Na、2,4-Dイソオクチルエステル、MCPAイソオクチルエステル、2,4-Dナトリウム塩、2,4-Dジメチルアミン塩、MCPA-チオエチル、MCPA、2,4-Dプロピオン酸、高2,4-Dプロピオン酸塩、2,4-D酪酸、MCPAプロピオン酸、MCPAプロピオン酸塩、MCPA酪酸、2,4,5-D、2,4,5-Dプロピオン酸、2,4,5-D酪酸、MCPAアミン塩、ジカンバ、エルボン、クロルフェナク、セゾン、TBA、クロラムベン、メトキシ-TBA、ジクロホップ-メチル、フルアジホップ-ブチル、フルアジホップ-p-ブチル、ハロキシホップ-メチル、ハロキシホップ-P、キザロホップ-エチル、キザロホップ-p-エチル、フェノキサプロップ-エチル、フェノキサプロップ-p-エチル、プロパキザホップ、シハロホップ-ブチル、メタミホップ、クロジナホップ-プロパルギル、フェンチアプロップ-エチル、クロロアジホップ-プロピニル、ポッペネート-メチル、トリホプシム、イソキサピリホップ、パラコート、ジクワット、オリザリン、エタルフルラリン、イソプロパリン、ニトラリン、プロフルラリン、プロジナミン、ベンフルラリン、フルクロラリン、ジニトラミナ、ジプロパリン、クロルニジン、メタルプロパリン、ジノプロップ、グリホセート、アニロホス、グルホシネートアンモニウム、アミプロホス-メチル、スルホセート、ピペロホス、ビアラホス-ナトリウム、ベンスリド、ブタミホス、ホカルブ、2,4-DEP、H-9201、ザイトロン、イマザピル、イマゼタピル、イマザキン、イマザモックス、イマザモックスアンモニウム塩、イマザピック、イマザメタベンズ-メチル、フルロキシピル、フルロキシピルメプチル、クロピラリド、ピクロラム、トリクロピル、ジチオピル、ハロキシジン、3,5,6-トリクロロ-2-ピリジノール、チアゾピル、フルリドン、アミノピラリド、ジフルフェンゾピル、トリクロピル-ブトチル、クリオジネート、セトキシジム、クレトジム、シクロキシジム、アロキシジム、プロホキシジム、ブトロキシジム、トラルコキシジム、テプラロキシジム、ブチダゾール、メトリブジン、ヘキサジノン、メタミトロン、エチオジン、アメトリジオン、アミブジン、ブロモキシニル、オクタン酸ブロモキシニル、オクタン酸イオキシニル、イオキシニル、ジクロベニル、ジフェナトリル、ピラクロニル、クロロキシニル、ヨードボニル、フルメツラム、フロラスラム、ペノキススラム、メトスラム、クロランスラム-メチル、ジクロスラム、ピロキススラム、ベンフレセート、ビスピリバック-ナトリウム、ピリベンゾキシム、ピリフタリド、ピリミノバック-メチル、ピリチオバック-ナトリウム、ベンゾビシロン、メソトリオン、スルコトリオン、テンボトリオン、テフリルトリオン、ビシクロピロン、ケトドピラドックス、イソキサフルトール、クロマゾン、フェノキサスルホン、メチオゾリン、フルアゾレート、ピラフルフェン-エチル、ピラゾリネート、ジフェンゾコート、ピラゾキシフェン、ベンゾフェナップ、ニピラクロフェン、ピラスルホトール、トプラメゾン、ピロキサスルホン、カフェンストロール、フルポキサム、アミノトリアゾール、アミノカルバゾン、アザフェニジン、カフェントラゾン-エチル、スルフェントラゾン、ベンカルバゾン、ベンズフェンジゾン、ブタフェナシル、ブロマシル、イソシル、レナシル、テルバシル、フルプロパシル、シニドン-エチル、フルミクロラック-ペンチル、フルミオキサジン、プロピザミド、MK-129、フルメジン、ペンタクロロフェノール、ジノセブ、ジノテルブ、酢酸ジノテルブ、ジノサム、DNOC、クロロニトロフェン、酢酸メジテルブ、ジノフェネート、オキサジアルギル、オキサジアゾン、ペントキサゾン、フルフェナセット、フルチアセット-メチル、フェントラザミド、フルフェンピル-エチル、ピラゾン、ブロムピラゾン、メトフルラゾン、クサキラ、ジミダゾン、オキサピラゾン、ノルフルラゾン、ピリダフォル、キンクロラック、キンメラック、ベンタゾン、ピリデート、オキサジクロメフォン、ベナゾリン、クロマゾン、シンメチリン、ZJ0702、ピリバンベンズ-プロピル、インダノファン、塩素酸ナトリウム、ダラポン、トリクロロ酢酸、モノクロロ酢酸、ヘキサクロロアセトン、フルプロパネート、シペルコート、ブロモクロフェノキシム、エプロナズ、メタゾール、フルルタモン、ベンフレセート、エトフメセート、チオクロリム、クロルタール、フルオロクロリドン、タブロン、アクロレイン、ベントラニル、トリジファン、クロルフェンプロプメチル、チジアリゾナイミン、フェニソファム、ブソキシノン、メトキシフェノン、サフルフェナシル、クラシフォス、クロロポン、アロラック、ジエタムコート、エトニプロミド、イプリミダム、イプフェンカルバゾン、チエンカルバゾン-メチル、ピリミスルファン、クロルフルラゾール、トリプロピンダン、サルグリカピン、プロスルファリン、カムベンジクロール、アミノシクロピラクロール、ロデタニル、ベノキサコール、フェノクロリム、フルラゾール、フェンクロラゾール-エチル、クロキントセット-メキシル、オキサベトリニル、MG/91、シオメトリニル、DKA-24、メフェンピル-ジエチル、フリラゾール、フルキソフェニル、イソキサジフェン-エチル、ジクロルミド、ハロキシフェン-メチル(halauxifen-methyl)、DOWフロルピラキシフェン、UBH-509、D489、LS82-556、KPP-300、NC-324、NC-330、KH-218、DPX-N8189、SC-0744、DOWCO535、DK-8910、V-53482、PP-600、MBH-001、KIH-9201、ET-751、KIH-6127およびKIH-2023。
Furthermore, compositions which can be combined with, for example, active compounds are known active compounds described, for example, in World Herbicide New Product Technology Handbook, China Agricultural Science and Farming Techniques Press, 2010.9 and the literature cited therein. is. For example, the following active compounds may be referred to as herbicides (note: these compounds are named according to the International Organization for Standardization (ISO) by their "common names" or, where appropriate, with their usual code numbers named by their chemical names): acetochlor, butachlor, alachlor, propisochlor, metolachlor, s-metolachlor, pretilachlor, propachlor, etachlor, napropamide, R-left handed napropamide, Propanil, Mefenacet, Difenamide, Diflufenican, Etaprochlor, Beflubutamide, Bromobutide, Dimethenamid, Dimethenamid-P, Etobenzanide, Flufenacet, Thenylchlor, Metazachlor, Isoxaben, Flamprop-M-methyl, Furamprop-M-propyl, Alidochlor , petoxamide, chloranocryl, cyprazine, mefluidide, monalide, delaclor, plinachlor, terbuchlor, xylachlor, dimethachlor, cisanilide, trimexachlor, clomeprop, propyzamide, pentanochlor, carbetaamide, benzoylprop-ethyl, ciprazole, butenachlor, tebutam , benzipram, moglutone, diclofluanid, naproanilide, diethyl-ethyl, naptalam, flufenacet, benzadox, chlorthiamid, chlorophthalimide, isocarbamide, picolinafen, atrazine, simazine, prometryn, cyanatrin, simetryne, ametrine, propazine, dipropethrin, SSH-108, terbutryn, terbuthylazine, triaziflam, cyprazine, proglinazine, trietadine, prometone, simetone, adiprothrin, desmethrin, dimethamethrin, procyanazine, mesoprazine, sebthylazine, secbumetone, terbumetone, metoprothrin, cyanatrin, ipadine, chlorazine, atraton, pendimethalin, eglinazine , cyanuric acid, indazifuram, chlorsulfuron, metsulfuron-methyl, bensulfuron-methyl, chlorimuron-ethyl, tribenuron-methyl, thifensulfuron-methyl, pyrazosulfuron-ethyl, mesosulfuron, iodosulfuron-methylsodium, foramsulfuron, cinosulfuron , triasulfuron, sulfometuron-methyl, nicosulfuron, etamethsulfuron-methyl le, amidosulfuron, ethoxysulfuron, cyclosulfamuron, rimsulfuron, azimsulfuron, flazasulfuron, monosulfuron, monosulfuron-ester, flucarbazone-sodium, flupyrsulfuron-methyl, halosulfuron-methyl, oxasulfuron, imazosulfuron, primisulfuron, propoxycarbazone, prosulfuron, sulfosulfuron, trifloxysulfuron, triflusulfuron-methyl, tritosulfuron, metsulfuron methyl sodium, flucetosulfuron, HNPC-C, orthosulfamuron, propyrisulfuron, metazosulfuron, acifluorfen, fomesafen, lactofen, fluoroglycofen, oxyfluorfen, chlornitrofen, acronifene, ethoxyfen-ethyl, bifenox, nitrofluorfen, clomethoxyphene, fluorodiphene, fluoronitrofen, furiloxyfen , nitrophen, TOPE, DMNP, PPG1013, AKH-7088, halosaphen, chlortoluron, isoproturon, linuron, diuron, daimuron, fluometuron, benzthiazuron, metabenzthiazuron, cumyluron, ethidimuron, isouron, tebuthiuron, buturon, chlorbromuron, methyl Daimuron, Fenobenzuron, SK-85, Metobromuron, Metoxuron, Monolinuron, Monuron, Cizuron, Fenuron, Fluothiuron, Nebulon, Chloroxuron, Noruron, Isonoron, 3-Cyclooctyl-1, Thiazflurone, Tebuthiuron, Difenoxuron, Parafluron, Methylamine, Tribunil, carbutyrate, trimetulon, dimeflon, monisouron, anisuron, methiuron, chlorethuron, tetraflurone, phenmedifam, phenmedifam-ethyl, desmedifam, aslam, terbucarb, barban, propham, chlorpropham, rowmate, swep, chlorbufam, carboxa Sol, Chlorprocarb, Fenasulam, BCPC, CPPC, Carbaslam, Butyrate, Bentocarb, Vernolate, Molinate, Trialate, Dimepiperate, Esprocarb, Piributicarb, Cycloate, Abadex, EPTC, Ethiolate, Orbencarb, Pevrate, Prosulfocarb, Thiocarbadil, CDEC, Jimeki Sano, isopolynate, methiobencarb, 2,4-D butyl ester, MCPA-Na, 2,4-D isooctyl ester, MCPA isooctyl ester, 2,4-D sodium salt, 2,4-D dimethylamine salt, MCPA-thioethyl, MCPA, 2,4-D propionic acid, high 2,4-D propionate, 2,4-D butyric acid, MCPA propionic acid, MCPA propionate, MCPA butyric acid, 2,4,5-D , 2,4,5-D propionic acid, 2,4,5-D butyric acid, MCPA amine salt, dicamba, Elvone, chlorfenac, saison, TBA, chloramben, methoxy-TBA, diclofop-methyl, fluazifop-butyl, fluazifop- p-butyl, haloxyfop-methyl, haloxyfop-P, quizalofop-ethyl, quizalofop-p-ethyl, fenoxaprop-ethyl, fenoxaprop-p-ethyl, propaxafop, cyhalofop-butyl, metamifop, clodinafop-propargyl, fenchiaprop-ethyl, chloroazifop-propynyl, poppenate-methyl, trifopsim, isoxapyrifop, paraquat, diquat, oryzarin, ethalfluralin, isopropaline, nitraline, profluralin, prodinamin, benfluralin, fluchlorarin, dinitramina, dipropaline, Chlornidin, metalpropaline, dinoprop, glyphosate, anilophos, glufosinate-ammonium, amiprophos-methyl, sulfosate, piperophos, bialaphos-sodium, benzulide, butamiphos, focarb, 2,4-DEP, H-9201, zytron, imazapyr, imazethapyr, imazaquin , imazamox, imazamox ammonium salt, imazapic, imazamethabenz-methyl, fluroxypyr, fluroxypyrmeptyl, clopyralid, picloram, triclopyr, dithiopyr, haloxydine, 3,5,6-trichloro-2-pyridinol, thiazopyr, fluridone, aminopyralid , diflufenzopyr, triclopyr-butotyl, cliodinate, sethoxydim, clethodim, cycloxydim, alloxydim, profoxydim, butroxydim, tralkoxydim, tepraloxydim, butidazole, metribuzine, hexazinone, metamitron, ethiozine, ametridione, amivudine, bromoxynil, bromoxynil octanoate, ioxynil octanoate, ioxynil, dichlobenil, diphenatril, pyraclonil, chloroxynil, iodobonil, flumetsulam, florasulam, penoxsulam, metosulam, cloransulam-methyl, diclosulam, pyroxsulam, benfuresate, bispyribac-sodium, pyribenzoxime, pyriftalide, pyriminobac-methyl, pyrithiobac-sodium, benzovicilone, mesotrione, sulcotrione, tembotrione, tefuryltrione, bicyclopyrone, ketodopyradox, isoxaflutole, clomazone, phenoxasulfone, methiozoline, fluazolate, pyraflufen-ethyl, pyrazolinate, difenzocort, pyrazoxifene, benzofenap, nipiraclofen, pyrasulfotol, topramezone, pyroxasulfone, caffenstrol, flupoxam, aminotriazole, aminocarbazone, azaphenidine, caffethrazone-ethyl, sulfentrazone, bencarbazone, benzfendizone, butaphenacil, bromacil, isocil, renacil , terbacil, flupropasil, sinidone-ethyl, flumicrolac-pentyl, flumioxazin, propyzamide, MK-129, flumedine, pentachlorophenol, dinoceb, dinoterb, dinoterb acetate, dinosum, DNOC, chloronitrophene, meziterb acetate, dinophenate, oxadiargyl , oxadiazone, pentoxazone, flufenacet, fluthiacet-methyl, fentrazamide, flufenpyra-ethyl, pyrazone, brompyrazone, methoflurazone, kusakira, dimidazone, oxapyrazone, norflurazone, pyridafol, quinclolac, quinmerac, bentazone, pyridate, oxadiclomefone , benzoline, clomazone, cymmethylin, ZJ0702, pyribambenz-propyl, indanophan, sodium chlorate, dalapon, trichloroacetic acid, monochloroacetic acid, hexachloroacetone, flupropanate, cyperquat, bromclofenoxime, apronaz, metazol, flulutamon, benfuresate, ethofumesate , thiochlorim, chlorthal, fluorochloridone, tabulone, acrolein, bentranil, tridiphane, chlorfenpropmethyl, thidiarizonaimine, phenisofam, busoxinone, methoxy phenone, saflufenacil, clasifos, chloropone, arolac, dietamcort, etonipromide, iprimidum, ipfencarbazone, thiencarbazone-methyl, pyrimisulphane, chlorflurazole, tripropindane, sarglycapine, prosulfarin, cambendichlor, aminocyclopyra Chlor, Rhodetanil, Benoxacol, Fenochlorim, Flurazole, Fenchlorazole-ethyl, Cloquintocet-mexyl, Oxabetrinil, MG/91, Xiometrinil, DKA-24, Mefenpyr-diethyl, Furilazole, Fluxophenyl, Isoxadifen-ethyl, Dichlormide , halauxifen-methyl, DOW Florpyraxifene, UBH-509, D489, LS82-556, KPP-300, NC-324, NC-330, KH-218, DPX-N8189, SC-0744, DOWCO 535, DK-8910, V-53482, PP-600, MBH-001, KIH-9201, ET-751, KIH-6127 and KIH-2023.
除草用組成物は、毒性緩和剤をさらに含んでもよく、それは、
a)ジクロロフェニルピラゾリン-3-カルボン酸(S1)タイプの化合物、好ましくは1-(2,4-ジクロロフェニル)-5-(エトキシカルボニル)-5-メチル-2-ピラゾリン-3-カルボン酸エチル(S1-1、メフェンピル-ジエチル、PM、pp.594-595)、および、例えばWO91/07874およびPM(pp.594-595)に記載されている関連化合物等の化合物;
b)ジクロロフェニルピラゾールカルボン酸誘導体、好ましくは1-(2,4-ジクロロフェニル)-5-メチルピラゾール-3-カルボン酸エチル(S1-2)、1-(2,4-ジクロロフェニル)-5-イソプロピルピラゾール-3-カルボン酸エチル(S1-3)、1-(2,4-ジクロロフェニル)-5-(1,1-ジメチル-エチル)ピラゾール-3-カルボン酸エチル(S1-4)、1-(2,4-ジクロロフェニル)-5-フェニルピラゾール-3-カルボン酸エチル(S1-5)、ならびにEP-A-333131およびEP-A-269806に記載されている関連化合物等の化合物;
c)トリアゾールカルボン酸(S1)タイプの化合物、好ましくはフェンクロラゾール等の化合物、すなわち1-(2,4-ジクロロフェニル)-5-トリクロロメチル-(1H)-1,2,4-トリアゾール-3-カルボン酸エチル(S1-6)および関連化合物(EP-A-174562およびEP-A-346620を参照されたい);
d)5-ベンジル-または5-フェニル-2-イソキサゾリン-3-カルボン酸タイプまたは5,5-ジフェニル-2-イソキサゾリン-3-カルボン酸タイプの化合物、好ましくは5-(2,4-ジクロロベンジル)-2-イソキサゾリン-3-カルボン酸エチル(S1-7)または5-フェニル-2-イソキサゾリン-3-カルボン酸エチル(S1-8)およびWO91/08202に記載されている関連化合物、または5,5-ジフェニル-2-イソキサゾリン-3-カルボン酸エチル(S1-9、イソキサジフェン-エチル)または5,5-ジフェニル-2-イソキサゾリン-3-カルボン酸n-プロピル(S1-10)または5-(4-フルオロフェニル)-5-フェニル-2-イソキサゾリン-3-カルボン酸エチル(S1-11)、特許出願(WO-A-95/07897)に記載されている関連化合物;
e)8-キノリンオキシ酢酸(S2)タイプの化合物、好ましくは1-メチルヘキサ-1-イル(5-クロロ-8-キノリノキシ)アセテート(S2-1、クロキントセット-メキシル、例えばPM(pp.195-196)、(1,3-ジメチルブト-1-イル)(5-クロロ-8-キノリノキシ)アセテート(S2-2)、4-アリルオキシブチル(5-クロロ-8-キノリノキシ)アセテート(S2-3)、1-アリルオキシプロプ-2-イル(5-クロロ-8-キノリノキシ)アセテート(S2-4)、(5-クロロ-8-キノリノキシ)酢酸エチル(S2-5)、(5-クロロ-8-キノリノキシ)酢酸メチル(S2-6)、(5-クロロ-8-キノリノキシ)酢酸アリル(S2-7)、2-(2-プロピリデンイミノオキシ)-1-エチル(5-クロロ-8-キノリノキシ)アセテート(S2-8)、2-オキソプロプ-1-イル(5-クロロ-8-キノリノキシ)アセテート(S2-9)およびEP-A-86750、EP-A-94349およびEP-A-191736またはEP-A-0492366に記載されている関連化合物;
f)(5-クロロ-8-キノリノキシ)マロン酸タイプの化合物、好ましくは(5-クロロ-8-キノリノキシ)マロン酸ジエチル、(5-クロロ-8-キノリノキシ)マロン酸ジアリル、(5-クロロ-8-キノリノキシ)-マロン酸メチルエチルEP-A-0582198に記載されているおよび関連化合物;
g)フェノキシ酢酸、フェノキシプロピオン酸または芳香族カルボン酸タイプの活性化合物、例えば2,4-ジクロロフェノキシ酢酸(およびエステル)(2,4-D)、2-(2-メチル-4-クロロフェノキシ)プロピオン酸エステル(メコプロップ)、MCPAまたは3,6-ジクロロ-2-メトキシ安息香酸(およびエステル)(ジカンバ)等;
h)ピリミジンタイプの活性化合物、例えば「フェンクロリム」(PM、pp.386-387)(=4,6-ジクロロ-2-フェニルピリミジン)等;
i)発芽前毒性緩和剤(土壌作用毒性緩和剤)として頻用されるジクロロアセトアミドタイプの活性化合物、例えば「ジクロロミド」(PM、pp.270-271)(=N,N-ジアリル-2,2-ジクロロアセトアミド)、「AR-29148」(=Stauffer製の3-ジクロロアセチル-2,2,5-トリメチル-1,3-オキサゾリドン)、“ベノキサコール”(PM、pp.74-75)(=4-ジクロロアセチル-3,4-ジヒドロ-3-メチル-2H-1,4-ベンゾオキサジン)、“APPG-1292”=PPG Industries製のN-アリル-N[(1,3-ジオキソラン-2-イル)-メチル]ジクロロアセトアミド)、「ADK-24」(=Sagro-Chem製のN-アリル-N-[(アリルアミノカルボニル)-メチル]-ジクロロアセトアミド)、「AAD-67」または「AMON4660」(=NirrokemiaまたはMonsanto製の3-ジクロロアセリル-1-オキサ-3-アザ-スピロ[4,5]デカン)、「ジクロノン」または「ABAS145138」または「ALAB145138」(=(=BASF製の3-ジクロロアセチル-2,5,5-トリメチル-1,3-ジアザビシクロ[4.3.0]ノナン)および「フリラゾール」または「AMON13900」(PM、482-483を参照されたい)(=(RS)-3-ジクロロアセチル-5-(2-フリル)-2,2-ジメチルオキサゾリドン)等;
j)ジクロロアセトン誘導体タイプの活性化合物、例えば「AMG191」(CAS登録番号96420-72-3)(=Nitrokemia製の2-ジクロロメチル-2-メチル-1,3-ジオキソラン)等;
k)シードドレッシング材料として知られているオキシイミノ化合物タイプの活性化合物、例えばメトラクロール損傷を防ぐためのシードドレッシングの毒性緩和剤として知られている「オキサベトリニル」(PM、p.689)(=(Z)-1,3-ジオキソラン-2-イルメトキシイミノ(フェニル)アセトニトリル)、メトラクロール損傷を防ぐためにシードドレッシングにおける毒性緩和剤として知られている「フルキソフェニム」(PM、pp.467-468)(=1-(4-クロロフェニル)-2,2,2-トリフルオロ-1-エタノンO-(1,3-ジオキソラン-2-イルメチル)-オキシム、およびメトラクロール損傷を防ぐためのシードドレッシングにおける毒性緩和剤として知られている「シオメトリニル」または「A-CGA-43089」(PM、p.983)(=(Z)-シアノメトキシイミノ(フェニル)アセトニトリル)等;
l)シードドレッシング材料として知られているチアゾールカルボン酸エステルタイプの活性化合物、例えばアラクロール損傷およびメトラクロール損傷を防ぐためのシードドレッシングにおける毒性緩和剤として知られている「フルラゾール」(PM、pp.450-451)(=2-クロロ-4-トリフルオロメチル-1,3-チアゾール-5-カルボン酸ベンジル)等;
m)シードドレッシング剤として知られているナフタレンジカルボン酸誘導体タイプの活性化合物、例えばチオカルバメート系除草剤損傷を防ぐためのシードドレッシングにおけるトウモロコシの毒性緩和剤として知られている「ナフタリン酸無水物」(PM、pp.1009-1010)(=1,8-ナフタレンジカルボン酸無水物)等;
n)クロマン酢酸誘導体タイプの活性化合物、例えばAmerican Cyanamid製の「ACL304415」(CAS登録番号31541-57-8)(=2-84-カルボキシクロマン-4-イル)酢酸等;
o)有害植物に対する除草作用に加えて、作物植物に対する毒性緩和剤作用を有する活性化合物、例えば「ジメピペレート」または「AMY-93」(PM、pp.302-303)(=S-1-メチル-1-フェニルエチルピペリジン-1-カルボチオエート)、「ダイムロン」または「ASK23」(PM、p.247)(=1-(1-メチル-1-フェニルエチル)-3-p-トリル尿素)、「クミルロン」=「AJC-940」(=3-(2-クロロフェニルメチル)-1-(1-メチル-1-フェニル-エチル)尿素、JP-A-60087254を参照されたい)、「メトキシフェノン」または「ANK049」(=3,3’-ジメチル-4-メトキシ-ベンゾフェノン)、「CSB」(=1-ブロモ-4-(クロロメチルスルホニル)ベンゼン)(Kumiai製のCAS登録番号54091-06-4)等
から選択される1種以上の化合物である。
The herbicidal composition may further comprise safeners, which are
a) compounds of the dichlorophenylpyrazoline-3-carboxylic acid (S1) type, preferably ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate ( S1-1, mefenpyr-diethyl, PM, pp.594-595) and related compounds such as those described in WO91/07874 and PM (pp.594-595);
b) dichlorophenylpyrazolecarboxylic acid derivatives, preferably ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), 1-(2,4-dichlorophenyl)-5-isopropylpyrazole -3-Ethyl carboxylate (S1-3), 1-(2,4-dichlorophenyl)-5-(1,1-dimethyl-ethyl)pyrazole-3-carboxylate (S1-4), 1-(2 ,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5) and related compounds described in EP-A-333131 and EP-A-269806;
c) compounds of the triazole carboxylic acid (S1) type, preferably compounds such as fenchlorazole, i.e. 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3 - ethyl carboxylates (S1-6) and related compounds (see EP-A-174562 and EP-A-346620);
d) 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid type or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid type compounds, preferably 5-(2,4-dichlorobenzyl )-ethyl 2-isoxazoline-3-carboxylate (S1-7) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-8) and related compounds described in WO 91/08202, or 5, Ethyl 5-diphenyl-2-isoxazoline-3-carboxylate (S1-9, isoxadifen-ethyl) or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-10) or 5-(4 -fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-11), a related compound described in patent application (WO-A-95/07897);
e) 8-quinolineoxyacetic acid (S2) type compounds, preferably 1-methylhex-1-yl(5-chloro-8-quinolinoxy)acetate (S2-1, cloquintocet-mexyl, eg PM (pp. 195 -196), (1,3-dimethylbut-1-yl)(5-chloro-8-quinolinoxy)acetate (S2-2), 4-allyloxybutyl (5-chloro-8-quinolinoxy)acetate (S2-3 ), 1-allyloxyprop-2-yl(5-chloro-8-quinolinoxy)acetate (S2-4), ethyl (5-chloro-8-quinolinoxy)acetate (S2-5), (5-chloro-8 -quinolinoxy)methyl acetate (S2-6), (5-chloro-8-quinolinoxy)allyl acetate (S2-7), 2-(2-propylideneiminoxy)-1-ethyl (5-chloro-8-quinolinoxy) ) acetate (S2-8), 2-oxoprop-1-yl(5-chloro-8-quinolinoxy)acetate (S2-9) and EP-A-86750, EP-A-94349 and EP-A-191736 or EP - related compounds described in A-0492366;
f) (5-chloro-8-quinolinoxy)malonic acid type compounds, preferably (5-chloro-8-quinolinoxy)malonate diethyl, (5-chloro-8-quinolinoxy)malonate diallyl, (5-chloro- 8-Quinolinoxy)-methylethyl malonate and related compounds described in EP-A-0582198;
g) active compounds of the phenoxyacetic acid, phenoxypropionic acid or aromatic carboxylic acid type, such as 2,4-dichlorophenoxyacetic acid (and esters) (2,4-D), 2-(2-methyl-4-chlorophenoxy) propionate (mecoprop), MCPA or 3,6-dichloro-2-methoxybenzoic acid (and esters) (dicamba), etc.;
h) active compounds of the pyrimidine type, such as "phenclolim" (PM, pp.386-387) (=4,6-dichloro-2-phenylpyrimidine);
i) active compounds of the dichloroacetamide type frequently used as preemergence safeners (soil safeners), such as "dichloromide" (PM, pp. 270-271) (=N,N-diallyl-2,2- dichloroacetamide), "AR-29148" (=3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidone from Stauffer), "Benoxacol" (PM, pp.74-75) (=4- dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine), "APPG-1292" = N-allyl-N [(1,3-dioxolan-2-yl) from PPG Industries -methyl]dichloroacetamide), "ADK-24" (=N-allyl-N-[(allylaminocarbonyl)-methyl]-dichloroacetamide from Sagro-Chem), "AAD-67" or "AMON4660" (= 3-dichloroaceryl-1-oxa-3-aza-spiro[4,5]decane from Nirrokemia or Monsanto), "Dichlonone" or "ABAS145138" or "ALAB145138" (=(=3-dichloroacetyl from BASF -2,5,5-trimethyl-1,3-diazabicyclo[4.3.0]nonane) and "furilazole" or "AMON 13900" (see PM, 482-483) (=(RS)-3- dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidone) and the like;
j) active compounds of the dichloroacetone derivative type, such as "AMG191" (CAS Registry Number 96420-72-3) (=2-dichloromethyl-2-methyl-1,3-dioxolane from Nitrokemia);
k) Active compounds of the oximino compound type known as seed dressing materials, e.g. "oxabetrinyl" (PM, p. 689), known as a safener in seed dressings to prevent metolachlor damage (=(Z )-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile), “fluxofenim” (PM, pp. 467-468), known as a safener in seed dressing to prevent metolachlor damage (= 1-(4-Chlorophenyl)-2,2,2-trifluoro-1-ethanone O-(1,3-dioxolan-2-ylmethyl)-oxime and safener in seed dressing to prevent metolachlor damage known as "Xiometrinyl" or "A-CGA-43089" (PM, p.983) (=(Z)-cyanomethoxyimino(phenyl)acetonitrile);
l) active compounds of the thiazole carboxylate type known as seed dressing materials, e.g. "flurazole" (PM, pp. 450-451) (=benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) and the like;
m) Active compounds of the naphthalene dicarboxylic acid derivative type known as seed dressing agents, e.g. "naphthalic anhydride", known as a safener of maize in seed dressings to prevent thiocarbamate herbicide damage ( PM, pp.1009-1010) (= 1,8-naphthalenedicarboxylic anhydride) and the like;
n) active compounds of the chromanacetic acid derivative type, such as "ACL304415" (CAS registry number 31541-57-8) (=2-84-carboxychroman-4-yl)acetic acid from American Cyanamid;
o) active compounds which, in addition to herbicidal action on harmful plants, have a safener action on crop plants, such as "dimepiperate" or "AMY-93" (PM, pp. 302-303) (=S-1-methyl- 1-phenylethylpiperidine-1-carbothioate), "Daimuron" or "ASK23" (PM, p.247) (= 1-(1-methyl-1-phenylethyl)-3-p-tolylurea), "cumyluron" = "AJC-940" (= 3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenyl-ethyl)urea, see JP-A-60087254), "methoxyphenone" or "ANK049"(=3,3'-dimethyl-4-methoxy-benzophenone),"CSB" (=1-bromo-4-(chloromethylsulfonyl)benzene) (CAS registration number 54091-06-4 manufactured by Kumiai ) and the like.
好ましい実施形態において、毒性緩和剤は、例えば、イソキサジフェン-エチル(CAS番号:163520-33-0)、シプロスルファミド(CAS番号:221667-31-8)、メフェンピル-ジエチル(CAS番号:135590-91-9)、クロキントセット-メキシル(CAS番号:99607-70-2)、ジベレリン酸(CAS番号:77-06-5)、フリラゾール(CAS番号:121776-33-8)およびメトカミフェン(CAS番号:129531-12-0)から選択される1種以上の化合物である。 In preferred embodiments, safeners are, for example, isoxadifen-ethyl (CAS number: 163520-33-0), cyprosulfamide (CAS number: 221667-31-8), mefenpyr-diethyl (CAS number: 135590- 91-9), cloquintocet-mexyl (CAS number: 99607-70-2), gibberellic acid (CAS number: 77-06-5), furilazole (CAS number: 121776-33-8) and metcamifene (CAS number: : 129531-12-0).
本発明の組成物は、使用者によって使用前に希釈されるか、またはそのまま使用され得る。組成物は、従来の処理方法、すなわち活性成分を液体溶媒または固体担体と混合し、次いで分散剤等の界面活性剤、安定剤、湿潤剤、接着剤、消泡剤の1種以上を添加することによって調製することができる。 The compositions of the present invention may be diluted prior to use by the user or used as is. The compositions are prepared by conventional processing, i.e. mixing the active ingredient with a liquid solvent or solid carrier and then adding one or more surfactants such as dispersing agents, stabilizers, wetting agents, adhesives, antifoaming agents. can be prepared by
除草用組成物は、分散性油懸濁液、水懸濁液、懸濁エマルジョン、水和剤、乳化性濃縮物、水分散性顆粒(乾燥懸濁液)、水性エマルジョンおよびマイクロエマルジョンから選択される剤形であり得る。 The herbicidal composition is selected from dispersible oil suspensions, water suspensions, suspension emulsions, wettable powders, emulsifiable concentrates, water dispersible granules (dry suspensions), aqueous emulsions and microemulsions. It can be a dosage form.
端的には、本発明の組成物は、従来技術の配合物において従来用いられている固体および液体の添加剤と混合することができる。外的条件が変化すると、用いられる有効成分の量も異なる。外部条件は、例えば、温度、湿度、用いられる除草剤の性質等である。それは、例えば、0.001~1.0kg/ha、またはより好ましくは0.005~750g/ha、特に0.005~500g/haの大きな変動範囲を有し得る。 Briefly, the compositions of the present invention can be mixed with solid and liquid additives conventionally used in prior art formulations. When the external conditions change, the amount of active ingredient used also varies. External conditions are, for example, temperature, humidity, properties of herbicides used, and the like. It can have a wide range of variation, for example from 0.001 to 1.0 kg/ha, or more preferably from 0.005 to 750 g/ha, especially from 0.005 to 500 g/ha.
本発明によれば、雑草を防除するための除草用組成物の使用も提供され;除草用組成物を植物、植物部分、植物種子または植物の栽培地域に適用することを含む、望ましくない植物の成長を制御するための方法が提供される。 According to the present invention there is also provided the use of the herbicidal composition for controlling weeds; Methods are provided for controlling growth.
さらに、本発明の組成物は、処理される植物の葉に噴霧することができ、すなわち、本発明の組成物は、雑草、特に雑草、および特に雑草が作物に侵入する、または侵入する可能性が高い雑草の表面に適用することができる。 In addition, the compositions of the invention can be sprayed onto the foliage of the plants to be treated, i.e. the compositions of the invention prevent weeds, in particular weeds, and in particular weeds from invading crops or the potential to infest crops. can be applied to surfaces with high weeds.
本発明の除草用組成物を適用すると、予想外の相乗効果が達成され、その除草活性は、各除草剤の単一または予測される活性の合計よりも大きい。相乗効果は、適用量の減少、より広い雑草防除スペクトル、およびより速くより耐久性のある除草作用によって明らかになり、これらはすべて雑草防除の実践に必要とされるものである。記載された特性に関して、組成物は、当技術分野における既存の除草剤よりも著しく優れている。組成物が当技術分野の既存の除草剤よりも少ない量で用いられるので、それはより環境に優しい。 When applying the herbicidal compositions of the present invention, an unexpected synergistic effect is achieved, the herbicidal activity being greater than the single or the sum of the expected activities of each herbicide. The synergistic effect is manifested by reduced application rates, broader weed control spectrum, and faster and more durable herbicidal action, all of which are required for weed control practice. With respect to the properties described, the compositions are significantly superior to existing herbicides in the art. Because the composition is used in lower amounts than existing herbicides in the art, it is more environmentally friendly.
本発明の相乗的除草用組成物はまた、以下の利点を有する:
(1)本発明の組成物は環境に優しく、環境中で容易に分解される;
(2)本発明の除草用組成物は、低コストで使用に便利であり、その普及および適用のために大きな経済的および社会的利益を有する。
The synergistic herbicidal compositions of the invention also have the following advantages:
(1) the composition of the present invention is environmentally friendly and easily degraded in the environment;
(2) The herbicidal composition of the present invention is low cost, convenient to use, and has great economic and social benefits due to its widespread use and application.
以下の実施例は、本発明を限定することを意図するものではなく、単に本発明がどのように実施されるかを説明することを意図するものである。これらの実施例は、特定の雑草に対して特に重要な効果を示す。実施例は次のとおりである。 The following examples are not intended to limit the invention, but merely to illustrate how the invention may be carried out. These examples show particularly important effects on certain weeds. Examples are as follows.
A)実施例
1.A1+メソトリオンの分散性油懸濁液(4+1:4%A1+1%メソトリオンを表す。以下同様である。)
A1+メソトリオン+0.3%クエン酸+5%ドデシルベンゼンスルホン酸カルシウム+8%ポリオキシエチレン脂肪アルコールエーテル+6%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+5%100#溶媒油+残余分のオレイン酸メチル
2.A1+トプラメゾン(3+1)の分散性油懸濁液
A1+トプラメゾン+5%ドデシルベンゼンスルホン酸カルシウム+6%ポリオキシエチレン脂肪アルコールエーテル+8%カルダノールポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+5%100#溶媒油+残余分のオレイン酸メチル
3.A1+ビピラゾン(3+1)の分散性油懸濁液
A1+ビピラゾン+0.2%クエン酸+5%ドデシルベンゼンスルホン酸カルシウム+6%ポリオキシエチレン脂肪アルコールエーテル+6%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+5%100#溶媒油+残余分のオレイン酸メチル
4.A1+フェンピラゾン(4+4)の分散性油懸濁液
A1+フェンピラゾン+5%ドデシルベンゼンスルホン酸カルシウム+8%ポリオキシエチレン脂肪アルコールエーテル+6%カルダノールポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+5%100#溶剤油+残余分のオレイン酸メチル
5.A1+イソキサフルトール(4+4)の分散性油懸濁液
A1+イソキサフルトール+0.2%クエン酸+5%ドデシルベンゼンスルホン酸カルシウム+8%ポリオキシエチレン脂肪アルコールエーテル+6%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+5%100#溶媒油+残余分のオレイン酸メチル
6.A1+クロマゾン(4+4)の分散性油懸濁液
A1+クロマゾン+4%ドデシルベンゼンスルホン酸カルシウム+6%カルダノールポリオキシエチレンエーテル+8%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+5%100#溶媒油+残余分のオレイン酸メチル
7.A1+ピラゾスルフロン-エチル(4+2)の分散性油懸濁液
A1+ピラゾスルフロン-エチル+0.5%尿素+5%ドデシルベンゼンスルホン酸カルシウム+8%ポリオキシエチレン脂肪アルコールエーテル+5%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+5%100#溶媒油+残余分のオレイン酸メチル
8.A1+ペノキススラム(4+1)の分散性油懸濁液
A1+ペノキススラム+5%ドデシルベンゼンスルホン酸カルシウム+6%脱水ソルビトールモノオレイン酸ポリオキシエチレンエーテル+5%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+5%100#溶媒油+残余分のオレイン酸メチル
9.A1+イマザモックス(4+1)の分散性油懸濁液
A1+イマザモックス+5%ドデシルベンゼンスルホン酸カルシウム+8%ポリオキシエチレン脂肪アルコールエーテル+6%カルダノールポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+5%100#溶剤油+残余分のオレイン酸メチル
10.A1+イマザピック(4+1)の分散性油懸濁液
A1+イマザピック+5%ドデシルベンゼンスルホン酸カルシウム+8%ポリオキシエチレン脂肪アルコールエーテル+6%カルダノールポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+5%100#溶媒油+残余分のオレイン酸メチル
11.A1+ビスピリバック-ナトリウム(4+1)の分散性油懸濁液
A1+ビスピリバック-ナトリウム+5%ドデシルベンゼンスルホン酸カルシウム+8%ポリオキシエチレン脂肪アルコールエーテル+5%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+5%100#溶媒油+残余分のオレイン酸メチル
12.A1+クレトジム(4+2)の分散性油懸濁液
A1+クレトジム+5%ドデシルベンゼンスルホン酸カルシウム+8%脱水ソルビトールモノオレイン酸ポリオキシエチレンエーテル+6%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+20%100#溶媒油+残余分のオレイン酸メチル
13.A1+セトキシジム(4+2)の分散性油懸濁液
A1+セトキシジム+5%ドデシルベンゼンスルホン酸カルシウム+8%脱水ソルビトールモノオレイン酸ポリオキシエチレンエーテル+7%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+6%100#溶媒油+残余分のオレイン酸メチル
14.A1+キザロホップ-P-メチル(4+2)の分散性油懸濁液
A1+キザロホップ-P-メチル+5%ドデシルベンゼンスルホン酸カルシウム+8%ポリオキシエチレン脂肪アルコールエーテル+5%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+10%100#溶媒油+残余分のオレイン酸メチル
15.A1+オキシフルオルフェン(3+1)の分散性油懸濁液
A1+オキシフルオルフェン+5%ドデシルベンゼンスルホン酸カルシウム+8%ポリオキシエチレン脂肪アルコールエーテル+6%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+20%100#溶剤油+残余分のオレイン酸メチル
16.A1+オキサジアゾン(3+1)の分散性油懸濁液
A1+オキサジアゾン+5%ドデシルベンゼンスルホン酸カルシウム+8%カルダノールポリオキシエチレンエーテル+6%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+5%100#溶媒油+残余分のオレイン酸メチル
17.A1+オキサジアルギル(3+1)の分散性油懸濁液
A1+オキサジアルギル+5%ドデシルベンゼンスルホン酸カルシウム+8%ポリオキシエチレン脂肪アルコールエーテル+6%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+15%100#溶剤油+残余分のオレイン酸メチル
18.A1+アトラジン(3+5)の水懸濁液
A1+アトラジン+5%ポリカルボキシレート+2%フェニルエチルフェノールポリオキシエチレンエーテルホスフェートトリエタノールアミン塩+0.25%キサンタンガム+2.5%ケイ酸アルミニウムマグネシウム+0.1%脱泡剤+3%エチレングリコール+残余分の水
19.A1+テルブチラジン(3+3)の水懸濁液
A1+テルブチラジン+5%ポリカルボキシレート+2%フェニルエチルフェノールポリオキシエチレンエーテルホスフェートトリエタノールアミン塩+0.25%キサンタンガム+2.5%ケイ酸アルミニウムマグネシウム+0.1%脱泡剤+3%エチレングリコール+残余分の水
20.A1+プロパニル(2+20)の水懸濁液
A1+プロパニル+5%ポリカルボキシレート+2%フェニルエチルフェノールポリオキシエチレンエーテルホスフェートトリエタノールアミン塩+0.16%キサンタンガム+1.6%ケイ酸アルミニウムマグネシウム+0.1%脱泡剤+3%エチレングリコール+残余分の水
21.A1+ベンタゾン(4+30)の水懸濁液
A1+ベンタゾン+5%ポリカルボキシレート+2%フェニルエチルフェノールポリオキシエチレンエーテルホスフェートトリエタノールアミン塩+0.1%キサンタンガム+1.2%ケイ酸アルミニウムマグネシウム+0.1%脱泡剤+3%エチレングリコール+残余分の水
22.A1+ブトラリン(4+21)の分散性油懸濁液
A1+ブトラリン+10%デカナミド+5%ドデシルベンゼンスルホン酸カルシウム+8%ポリオキシエチレン脂肪アルコールエーテル+7%ヒマシ油ポリオキシエチレンエーテル+1%オルガノベントナイト+1%ヒュームドシリカ+15%100#溶剤油+残余分のオレイン酸メチル
23.A1+ペンジメタリン(4+21)の分散性油懸濁液
A1+ペンジメタリン+10%デカナミド+6%ドデシルベンゼンスルホン酸カルシウム+8%ポリオキシエチレン脂肪アルコールエーテル+5%ヒマシ油ポリオキシエチレンエーテル+1%オルガノベントナイト+1%ヒュームドシリカ+10%100#溶媒油+残余分のオレイン酸メチル
24.A1+ブタクロール(4+6)の分散性油懸濁液
A1+ブタクロール+6%ドデシルベンゼンスルホン酸カルシウム+6%ポリオキシエチレン脂肪アルコールエーテル+8%カルダノールポリオキシエチレンエーテル+3%オルガノベントナイト+3%ヒュームドシリカ+残余分のオレイン酸メチル
25.A1+プレチラクロール(2+4)の分散性油懸濁液
A1+プレチラクロール+5%ドデシルベンゼンスルホン酸カルシウム+6%ポリオキシエチレン脂肪アルコールエーテル+8%カルダノールポリオキシエチレンエーテル+3%オルガノベントナイト+3%ヒュームドシリカ+残余分のオレイン酸メチル
26.A1+アニロホス(4+2)の分散性油懸濁液
A1+アニロホス+5%ドデシルベンゼンスルホン酸カルシウム+8%カルダノールポリオキシエチレンエーテル+7%ヒマシ油ポリオキシエチレンエーテル+3%オルガノベントナイト+3%ヒュームドシリカ+12%100#溶剤油+残余分のオレイン酸メチル
27.A1+キンクロラック(2+10)の分散性油懸濁液
A1+キンクロラック+5%ドデシルベンゼンスルホン酸カルシウム+8%ポリオキシエチレン脂肪アルコールエーテル+6%ヒマシ油ポリオキシエチレンエーテル+2.0%オルガノベントナイト+2.0%ヒュームドシリカ+10%100#溶剤油+残余分のオレイン酸メチル
28.A1+フルオロキシピル(2+3)の分散性油懸濁液
A1+フルオロキシピル+5%ドデシルベンゼンスルホン酸カルシウム+8%フェニルエチルフェノールポリオキシエチレンエーテル+6%ヒマシ油ポリオキシエチレンエーテル+3%オルガノベントナイト+3%ヒュームドシリカ+10%100#溶剤油+残余分のオレイン酸メチル
29.A1+フロルピラキシフェンベンジル(3+1)の分散性油懸濁液
A1+フロルピロキシフェンベンジル+5%ドデシルベンゼンスルホン酸カルシウム+8%ポリオキシエチレン脂肪アルコールエーテル+6%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+残余分のオレイン酸メチル
30.A1+MCPA(3+10)の分散性油懸濁液
A1+MCPA+6%ドデシルベンゼンスルホン酸カルシウム+8%カルダノールポリオキシエチレンエーテル+6%ヒマシ油ポリオキシエチレンエーテル+2%オルガノベントナイト+2.5%ヒュームドシリカ+12%100#溶剤油+残余分のオレイン酸メチル
31.A1+グリホサート(4+16)の水懸濁液
A1+グリホセート+5%ポリカルボキシレート+2%フェニルエチルフェノールポリオキシエチレンエーテルホスフェートトリエタノールアミン塩+3%プロピレングリコールブロックポリエーテル+0.2%耐塩性キサンタンガム+2.0%ケイ酸アルミニウムマグネシウム+0.1%脱泡剤+3%エチレングリコール+残余分の水
32.A1+グルホシネートアンモニウム(3+15)の水懸濁液
A1+グルホシネートアンモニウム+5%ポリカルボキシレート+2%フェニルエチルフェノールポリオキシエチレンエーテルホスフェートトリエタノールアミン塩+3%プロピレングリコールブロックポリエーテル+0.2%耐塩性キサンタンガム+2.0%ケイ酸アルミニウムマグネシウム+0.1%脱泡剤+3%エチレングリコール+残余分の水
33.A1+二臭化二臭化二水和物(4+15)の水懸濁液
A1+二臭化ジクワット一水和物+5%ポリカルボキシレート+2%フェニルエチルフェノールポリオキシエチレンエーテルホスフェートトリエタノールアミン塩+3%プロピレングリコールブロックポリエーテル+0.2%耐塩性キサンタンガム+2.0%ケイ酸アルミニウムマグネシウム+0.1%脱泡剤+3%エチレングリコール+残余分の水
34.A1+シンメチリン(4+1)の分散性油懸濁液
A1+シンメチリン+5%ドデシルベンゼンスルホン酸カルシウム+8%ポリオキシエチレン脂肪アルコールエーテル+6%ヒマシ油ポリオキシエチレンエーテル+3%オルガノベントナイト+2%ヒュームドシリカ+12%100#溶剤油+残余分のオレイン酸メチル
35.A2+メソトリオン(4+1)の分散性油懸濁液
A2+メソトリオン+0.2%クエン酸+5%ドデシルベンゼンスルホン酸カルシウム+8%ポリオキシエチレン脂肪アルコールエーテル+6%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+5%100#溶媒油+残余分のオレイン酸メチル
36.A2+トプラメゾン(3+1)の分散性油懸濁液
A2+トプラメゾン+5%ドデシルベンゼンスルホン酸カルシウム+8%ポリオキシエチレン脂肪アルコールエーテル+7%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+5%100#溶剤油+残余分のオレイン酸メチル
37.A2+ビピラゾン(3+1)の分散性油懸濁液
A2+ビピラゾン+0.2%クエン酸+5%ドデシルベンゼンスルホン酸カルシウム+9%ポリオキシエチレン脂肪アルコールエーテル+6%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+5%100#溶剤油+残余分のオレイン酸メチル
38.A2+フェンピラゾン(4+4)の分散性油懸濁液
A2+フェンピラゾン+0.2%クエン酸+5%ドデシルベンゼンスルホン酸カルシウム+9%カルダノールポリオキシエチレンエーテル+6%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+5%100#溶媒油+残余分のオレイン酸メチル
39.A2+イソキサフルトール(4+4)の分散性油懸濁液
A2+イソキサフルトール+0.3%クエン酸+5%ドデシルベンゼンスルホン酸カルシウム+9%ポリオキシエチレン脂肪アルコールエーテル+6%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+5%100#溶媒油+残余分のオレイン酸メチル
40.A2+クロマゾン(4+4)の分散性油懸濁液
A2+クロマゾン+6%ドデシルベンゼンスルホン酸カルシウム+8%ポリオキシエチレン脂肪アルコールエーテル+7%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+10%100#溶媒油+残余分のオレイン酸メチル
41.A2+ピラゾスルフロン-エチル(4+2)の分散性油懸濁液
A2+ピラゾスルフロン-エチル+0.5%尿素+5%ドデシルベンゼンスルホン酸カルシウム+7%ポリオキシエチレン脂肪アルコールエーテル+8%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+5%100#溶媒油+残余分のオレイン酸メチル
42.A2+ペノキススラム(4+1)の分散性油懸濁液
A2+ペノキススラム+5%ドデシルベンゼンスルホン酸カルシウム+9%脱水ソルビトールモノオレイン酸ポリオキシエチレンエーテル+5%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+5%100#溶媒油+残余分のオレイン酸メチル
43.A2+イマザモックス(4+1)の分散性油懸濁液
A2+イマザモックス+5%ドデシルベンゼンスルホン酸カルシウム+9%ポリオキシエチレン脂肪アルコールエーテル+5%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+5%100#溶剤油+残余分のオレイン酸メチル
44.A2+イマザピック(4+1)の分散性油懸濁液
A2+イマザピック+5%ドデシルベンゼンスルホン酸カルシウム+9%ポリオキシエチレン脂肪アルコールエーテル+5%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+5%100#溶剤油+残余分のオレイン酸メチル
45.A2+ビスピリバック-ナトリウム(4+1)の分散性油懸濁液
A2+ビスピリバック-ナトリウム+5%ドデシルベンゼンスルホン酸カルシウム+9%ポリオキシエチレン脂肪アルコールエーテル+5%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+5%100#溶剤油+残余分のオレイン酸メチル
46.A2+クレトジム(4+2)の分散性油懸濁液
A2+クレトジム+5%ドデシルベンゼンスルホン酸カルシウム+9%ポリオキシエチレン脂肪アルコールエーテル+6%ヒマシ油ポリオキシエチレンエーテル+3%オルガノベントナイト+2%ヒュームドシリカ+20%100#溶剤油+残余分のオレイン酸メチル
47.A2+セトキシジム(4+2)の分散性油懸濁液
A2+セトキシジム+5%ドデシルベンゼンスルホン酸カルシウム+9%ポリオキシエチレン脂肪アルコールエーテル+7%ヒマシ油ポリオキシエチレンエーテル+3%オルガノベントナイト+2%ヒュームドシリカ+6%100#溶媒油+残余分のオレイン酸メチル
48.A2+キザロホップ-P-メチル(4+2)の分散性油懸濁液
A2+キザロホップ-P-メチル+5%ドデシルベンゼンスルホン酸カルシウム+8%ポリオキシエチレン脂肪アルコールエーテル+8%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+6%100#溶剤油+残余分のオレイン酸メチル
49.A2+オキシフルオルフェン(3+1)の分散性油懸濁液
A2+オキシフルオルフェン+5%ドデシルベンゼンスルホン酸カルシウム+8%カルダノールポリオキシエチレンエーテル+6%ヒマシ油ポリオキシエチレンエーテル+3%オルガノベントナイト+2%ヒュームドシリカ+20%100#溶剤油+残余分のオレイン酸メチル
50.A2+オキサジアゾン(3+1)の分散性油懸濁液
A2+オキサジアゾン+5%ドデシルベンゼンスルホン酸カルシウム+8%ポリオキシエチレン脂肪アルコールエーテル+6%ヒマシ油ポリオキシエチレンエーテル+3%オルガノベントナイト+5%100#溶媒油+残余分のオレイン酸メチル
51.A2+オキサジアルギル(3+1)の分散性油懸濁液
A2+オキサジアルギル+5%ドデシルベンゼンスルホン酸カルシウム+8%ポリオキシエチレン脂肪アルコールエーテル+6%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+2%ヒュームドシリカ+15%100#溶媒油+残余分のオレイン酸メチル
52.A2+アトラジン(3+5)の水懸濁液
A2+アトラジン+5%ポリカルボキシレート+2%フェニルエチルフェノールポリオキシエチレンエーテルホスフェートトリエタノールアミン塩+0.22%キサンタンガム+2.2%ケイ酸アルミニウムマグネシウム+0.1%脱泡剤+3%エチレングリコール+残余分の水
53.A2+テルブチラジン(3+3)の水懸濁液
A2+テルブチラジン+5%ポリカルボキシレート+2%フェニルエチルフェノールポリオキシエチレンエーテルホスフェートトリエタノールアミン塩+0.26%キサンタンガム+2.2%ケイ酸アルミニウムマグネシウム+0.1%脱泡剤+3%エチレングリコール+残余分の水
54.A2+プロパニル(2+20)の水懸濁液
A2+プロパニル+5%ポリカルボキシレート+2%フェニルエチルフェノールポリオキシエチレンエーテルホスフェートトリエタノールアミン塩+0.18%キサンタンガム+1.8%ケイ酸アルミニウムマグネシウム+0.1%脱泡剤+3%エチレングリコール+残余分の水
55.A2+ベンタゾン(4+30)の水懸濁液
A2+ベンタゾン+5%ポリカルボキシレート+2%フェニルエチルフェノールポリオキシエチレンエーテルホスフェートトリエタノールアミン塩+0.12%キサンタンガム+1.5%ケイ酸アルミニウムマグネシウム+0.1%脱泡剤+3%エチレングリコール+残余分の水
56.A2+ブトラリン(4+21)の分散性油懸濁液
A2+ブトラリン+10%デカナミド+5%ドデシルベンゼンスルホン酸カルシウム+9%ポリオキシエチレン脂肪アルコールエーテル+7%ヒマシ油ポリオキシエチレンエーテル+1%オルガノベントナイト+1%ヒュームドシリカ+10%100#溶媒油+残余分のオレイン酸メチル
57.A2+ペンジメタリン(4+21)の分散性油懸濁液
A2+ペンジメタリン+10%デカナミド+6%ドデシルベンゼンスルホン酸カルシウム+9%ポリオキシエチレン脂肪アルコールエーテル+5%ヒマシ油ポリオキシエチレンエーテル+1%オルガノベントナイト+1%ヒュームドシリカ+10%100#溶媒油+残余分のオレイン酸メチル
58.A2+ブタクロール(4+6)の分散性油懸濁液
A2+ブタクロール+6%ドデシルベンゼンスルホン酸カルシウム+9%カルダノールポリオキシエチレンエーテル+7%ヒマシ油ポリオキシエチレンエーテル+3%オルガノベントナイト+2%ヒュームドシリカ+残余分のオレイン酸メチル
59.A2+プレチラクロール(2+4)の分散性油懸濁液
A2+プレチラクロール+5%ドデシルベンゼンスルホン酸カルシウム+9%カルダノールポリオキシエチレンエーテル+7%ヒマシ油ポリオキシエチレンエーテル+3%オルガノベントナイト+2%ヒュームドシリカ+残余分のオレイン酸メチル
60.A2+アニロホス(4+2)の分散性油懸濁液
A2+アニロホス+5%ドデシルベンゼンスルホン酸カルシウム+9%ポリオキシエチレン脂肪アルコールエーテル+7%ヒマシ油ポリオキシエチレンエーテル+3%オルガノベントナイト+2%ヒュームドシリカ+12%100#溶媒油+残余分のオレイン酸メチル
61.A2+キンクロラック(2+10)の分散性油懸濁液
A2+キンクロラック+5%ドデシルベンゼンスルホン酸カルシウム+9%ポリオキシエチレン脂肪アルコールエーテル+6%ヒマシ油ポリオキシエチレンエーテル+2.5%オルガノベントナイト+10%100#溶媒油+残余分のオレイン酸メチル
62.A2+フルオロキシピル(2+3)の分散性油懸濁液
A2+フルオロキシピル+5%ドデシルベンゼンスルホン酸カルシウム+9%フェニルエチルフェノールポリオキシエチレンエーテル+6%ヒマシ油ポリオキシエチレンエーテル+3%オルガノベントナイト+3%ヒュームドシリカ+10%100#溶媒油+残余分のオレイン酸メチル
63.A2+フロルピラキシフェンベンジル(3+1)の分散性油懸濁液
A2+フロルピロキシフェンベンジル+5%ドデシルベンゼンスルホン酸カルシウム+9%ポリオキシエチレン脂肪アルコールエーテル+6%ヒマシ油ポリオキシエチレンエーテル+3%オルガノベントナイト+2%ヒュームドシリカ+12%100#溶剤油+残余分のオレイン酸メチル
64.A2+MCPA(3+10)の分散性油懸濁液
A2+MCPA+6%ドデシルベンゼンスルホン酸カルシウム+9%ポリオキシエチレン脂肪アルコールエーテル+6%ヒマシ油ポリオキシエチレンエーテル+2%オルガノベントナイト+1%ヒュームドシリカ+12%100#溶媒油+残余分のオレイン酸メチル
65.A2+グリホサート(4+16)の水懸濁液
A2+グリホセート+5%ポリカルボキシレート+2%フェニルエチルフェノールポリオキシエチレンエーテルホスフェートトリエタノールアミン塩+3%プロピレングリコールブロックポリエーテル+0.2%耐塩性キサンタンガム+1%ケイ酸アルミニウムマグネシウム+0.1%脱泡剤+3%エチレングリコール+残余分の水
66.A2+グルホシネートアンモニウム(3+15)の水懸濁液
A2+グルホシネートアンモニウム+5%ポリカルボキシレート+2%フェニルエチルフェノールポリオキシエチレンエーテルホスフェートトリエタノールアミン塩+3%プロピレングリコールブロックポリエーテル+0.2%耐塩性キサンタンガム+1%ケイ酸アルミニウムマグネシウム+0.1%脱泡剤+3%エチレングリコール+残余分の水
67.A2+二臭化二臭化二水和物(4+15)の水懸濁液
A2+ジクワットジブロミド一水和物+5%ポリカルボキシレート+2%フェニルエチルフェノールポリオキシエチレンエーテルホスフェートトリエタノールアミン塩+3%プロピレングリコールブロックポリエーテル+0.2%耐塩性キサンタンガム+1%ケイ酸アルミニウムマグネシウム+0.1%脱泡剤+3%エチレングリコール+残余分の水
68.A2+シンメチリン(4+1)の分散性油懸濁液
A2+シンメチリン+5%ドデシルベンゼンスルホン酸カルシウム+9%ポリオキシエチレン脂肪アルコールエーテル+6%ヒマシ油ポリオキシエチレンエーテル+3%オルガノベントナイト+2%ヒュームドシリカ+10%100#溶媒油+残余分のオレイン酸メチル。
A) Example 1. Dispersible oil suspension of A1 + mesotrione (4 + 1: represents 4% A1 + 1% mesotrione, and so on.)
A1 + mesotrione + 0.3% citric acid + 5% calcium dodecylbenzenesulfonate + 8% polyoxyethylene fatty alcohol ether + 6% castor oil polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 100# solvent oil + balance min methyl oleate 2 . A1 + dispersible oil suspension of topramezone (3+1) A1 + topramezone + 5% calcium dodecylbenzenesulfonate + 6% polyoxyethylene fatty alcohol ether + 8% cardanol polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 3. 100# solvent oil + residual methyl oleate. A1 + dispersible oil suspension of bipyrazone (3+1) A1 + bipyrazone + 0.2% citric acid + 5% calcium dodecylbenzenesulfonate + 6% polyoxyethylene fatty alcohol ether + 6% castor oil polyoxyethylene ether + 2.5% organobentonite + 2 % fumed silica + 5% 100# solvent oil + balance methyl oleate 4. A1 + Dispersible Oil Suspension of Fenpyrazone (4+4) A1 + Fenpyrazone + 5% calcium dodecylbenzenesulfonate + 8% polyoxyethylene fatty alcohol ether + 6% cardanol polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 5. 100# solvent oil + residual methyl oleate. A1 + dispersible oil suspension of isoxaflutole (4+4) A1 + isoxaflutole + 0.2% citric acid + 5% calcium dodecylbenzenesulfonate + 8% polyoxyethylene fatty alcohol ether + 6% castor oil polyoxyethylene ether + 2 5% organobentonite + 2% fumed silica + 5% 100# solvent oil + balance methyl oleate 6. A1 + dispersible oil suspension of clomazone (4+4) A1 + clomazone + 4% calcium dodecylbenzene sulfonate + 6% cardanol polyoxyethylene ether + 8% castor oil polyoxyethylene ether + 2.5% organobentonite + 5% 100# solvent oil + 6. residual methyl oleate; Dispersible oil suspension of A1 + pyrazosulfuron-ethyl (4+2) A1 + pyrazosulfuron-ethyl + 0.5% urea + 5% calcium dodecylbenzenesulfonate + 8% polyoxyethylene fatty alcohol ether + 5% castor oil polyoxyethylene ether + 2.5% Organo bentonite + 2% fumed silica + 5% 100# solvent oil + balance methyl oleate 8. A1 + Dispersible Oil Suspension of Penoxsulam (4+1) A1 + Penoxsulam + 5% Calcium Dodecylbenzene Sulfonate + 6% Dehydrated Sorbitol Monooleate Polyoxyethylene Ether + 5% Castor Oil Polyoxyethylene Ether + 2.5% Organobentonite + 2% Fumed Silica + 5% 100# solvent oil + balance methyl oleate 9. A1 + dispersible oil suspension of imazamox (4+1) A1 + imazamox + 5% calcium dodecylbenzenesulfonate + 8% polyoxyethylene fatty alcohol ether + 6% cardanol polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 100# solvent oil + residual methyl oleate 10. A1 + dispersible oil suspension of imazapic (4+1) A1 + imazapic + 5% calcium dodecylbenzenesulfonate + 8% polyoxyethylene fatty alcohol ether + 6% cardanol polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 100# solvent oil + residual methyl oleate 11. A1 + bispyribac-sodium (4+1) dispersible oil suspension A1 + bispyribac-sodium + 5% calcium dodecylbenzenesulfonate + 8% polyoxyethylene fatty alcohol ether + 5% castor oil polyoxyethylene ether + 2.5% organobentonite + 2% fume silica + 5% 100# solvent oil + balance methyl oleate 12. A1 + dispersible oil suspension of clethodim (4+2) A1 + clethodim + 5% calcium dodecylbenzenesulfonate + 8% dehydrated sorbitol monooleate polyoxyethylene ether + 6% castor oil polyoxyethylene ether + 2.5% organobentonite + 2% fumed Silica + 20% 100# solvent oil + balance methyl oleate 13. A1 + dispersible oil suspension of sethoxydim (4+2) A1 + sethoxydim + 5% calcium dodecylbenzenesulfonate + 8% dehydrated sorbitol monooleate polyoxyethylene ether + 7% castor oil polyoxyethylene ether + 2.5% organobentonite + 2% fumed Silica + 6% 100# solvent oil + balance methyl oleate 14. Dispersible oil suspension of A1 + quizalofop-P-methyl (4+2) A1 + quizalofop-P-methyl + 5% calcium dodecylbenzenesulfonate + 8% polyoxyethylene fatty alcohol ether + 5% castor oil polyoxyethylene ether + 2.5% organo Bentonite + 2% fumed silica + 10% 100# solvent oil + balance methyl oleate 15. A1 + dispersible oil suspension of oxyfluorphen (3+1) A1 + oxyfluorphen + 5% calcium dodecylbenzene sulfonate + 8% polyoxyethylene fatty alcohol ether + 6% castor oil polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 20% 100# solvent oil + residual methyl oleate 16. A1 + Dispersible Oil Suspension of Oxadiazone (3+1) A1 + Oxadiazone + 5% calcium dodecylbenzenesulfonate + 8% cardanol polyoxyethylene ether + 6% castor oil polyoxyethylene ether + 2.5% organobentonite + 5% 100# solvent oil + residual methyl oleate 17 . A1 + dispersible oil suspension of oxadiargyl (3+1) A1 + oxadiargyl + 5% calcium dodecylbenzenesulfonate + 8% polyoxyethylene fatty alcohol ether + 6% castor oil polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 15% 100# solvent oil + residual methyl oleate 18. A1 + suspension of atrazine (3+5) in water A1 + atrazine + 5% polycarboxylate + 2% phenylethylphenol polyoxyethylene ether phosphate triethanolamine salt + 0.25% xanthan gum + 2.5% magnesium aluminum silicate + 0.1% defoaming agent + 3% ethylene glycol + balance water 19. A1 + terbuthylazine (3+3) suspension in water A1 + terbuthylazine + 5% polycarboxylate + 2% phenylethylphenol polyoxyethylene ether phosphate triethanolamine salt + 0.25% xanthan gum + 2.5% aluminum magnesium silicate + 0.1% defoaming agent + 3% ethylene glycol + balance water 20. A1 + propanyl (2+20) suspension in water A1 + propanyl + 5% polycarboxylate + 2% phenylethylphenol polyoxyethylene ether phosphate triethanolamine salt + 0.16% xanthan gum + 1.6% aluminum magnesium silicate + 0.1% defoaming agent + 3% ethylene glycol + balance water 21. A1 + suspension of bentazone (4+30) in water A1 + bentazone + 5% polycarboxylate + 2% phenylethylphenol polyoxyethylene ether phosphate triethanolamine salt + 0.1% xanthan gum + 1.2% aluminum magnesium silicate + 0.1% defoaming agent + 3% ethylene glycol + balance water 22. A1 + dispersible oil suspension of butaline (4+21) A1 + butaline + 10% decanamide + 5% calcium dodecylbenzenesulfonate + 8% polyoxyethylene fatty alcohol ether + 7% castor oil polyoxyethylene ether + 1% organobentonite + 1% fumed silica + 15 % 100# solvent oil + balance methyl oleate 23. A1 + dispersible oil suspension of pendimethalin (4+21) A1 + pendimethalin + 10% decanamide + 6% calcium dodecylbenzenesulfonate + 8% polyoxyethylene fatty alcohol ether + 5% castor oil polyoxyethylene ether + 1% organobentonite + 1% fumed silica + 10 % 100# solvent oil + balance methyl oleate 24. A1 + dispersible oil suspension of butachlor (4+6) A1 + butachlor + 6% calcium dodecylbenzene sulfonate + 6% polyoxyethylene fatty alcohol ether + 8% cardanol polyoxyethylene ether + 3% organobentonite + 3% fumed silica + balance of Methyl oleate 25 . A1 + dispersible oil suspension of pretilachlor (2+4) A1 + pretilachlor + 5% calcium dodecylbenzene sulfonate + 6% polyoxyethylene fatty alcohol ether + 8% cardanol polyoxyethylene ether + 3% organobentonite + 3% fumed silica + balance Methyl oleate 26 . Dispersible Oil Suspension of A1 + Anilophos (4+2) A1 + Anilophos + 5% calcium dodecylbenzenesulfonate + 8% cardanol polyoxyethylene ether + 7% castor oil polyoxyethylene ether + 3% organobentonite + 3% fumed silica + 12% 100# Solvent oil + residual methyl oleate 27 . A1 + dispersible oil suspension of quinclolac (2+10) A1 + quinclolac + 5% calcium dodecylbenzenesulfonate + 8% polyoxyethylene fatty alcohol ether + 6% castor oil polyoxyethylene ether + 2.0% organobentonite + 2.0% fume silica + 10% 100# solvent oil + residual methyl oleate 28. A1 + Dispersible Oil Suspension of Fluoroxypyr (2+3) A1 + Fluoroxypyr + 5% calcium dodecylbenzenesulfonate + 8% phenylethylphenol polyoxyethylene ether + 6% castor oil polyoxyethylene ether + 3% organobentonite + 3% fumed Silica + 10% 100# solvent oil + balance methyl oleate 29. A1 + Dispersible Oil Suspension of Florpyraxifene Benzyl (3+1) A1 + Florpyroxifene Benzyl + 5% Calcium Dodecylbenzene Sulfonate + 8% Polyoxyethylene Fatty Alcohol Ether + 6% Castor Oil Polyoxyethylene Ether + 2.5% Organo Bentonite + 2% fumed silica + balance methyl oleate 30. Dispersible Oil Suspension of A1 + MCPA (3+10) A1 + MCPA + 6% calcium dodecylbenzene sulfonate + 8% cardanol polyoxyethylene ether + 6% castor oil polyoxyethylene ether + 2% organobentonite + 2.5% fumed silica + 12% 100# solvent Oil + residual methyl oleate 31 . A1 + suspension of glyphosate (4+16) in water A1 + glyphosate + 5% polycarboxylate + 2% phenylethylphenol polyoxyethylene ether phosphate triethanolamine salt + 3% propylene glycol block polyether + 0.2% salt tolerant xanthan gum + 2.0% silica Magnesium aluminum acid + 0.1% defoamer + 3% ethylene glycol + balance water 32 . A1 + Aqueous Suspension of Glufosinate Ammonium (3+15) A1 + Glufosinate Ammonium + 5% Polycarboxylate + 2% Phenylethylphenol Polyoxyethylene Ether Phosphate Triethanolamine Salt + 3% Propylene Glycol Block Polyether + 0.2% Salt Tolerant Xanthan Gum + 2.0 % magnesium aluminum silicate + 0.1% defoamer + 3% ethylene glycol + balance water 33 . A1 + dibromide dibromide dihydrate (4+15) suspension in water A1 + dibromide diquat monohydrate + 5% polycarboxylate + 2% phenylethylphenol polyoxyethylene ether phosphate triethanolamine salt + 3% propylene 34. Glycol block polyether + 0.2% salt tolerant xanthan gum + 2.0% magnesium aluminum silicate + 0.1% defoamer + 3% ethylene glycol + balance water. A1 + dispersible oil suspension of cymmethylin (4+1) A1 + cymmethylin + 5% calcium dodecylbenzene sulfonate + 8% polyoxyethylene fatty alcohol ether + 6% castor oil polyoxyethylene ether + 3% organobentonite + 2% fumed silica + 12% 100# Solvent oil + residual methyl oleate 35 . A2 + dispersible oil suspension of mesotrione (4+1) A2 + mesotrione + 0.2% citric acid + 5% calcium dodecylbenzenesulfonate + 8% polyoxyethylene fatty alcohol ether + 6% castor oil polyoxyethylene ether + 2.5% organobentonite + 2 % fumed silica + 5% 100# solvent oil + balance methyl oleate 36. A2 + dispersible oil suspension of topramezone (3+1) A2 + topramezone + 5% calcium dodecylbenzene sulfonate + 8% polyoxyethylene fatty alcohol ether + 7% castor oil polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 37. 100# solvent oil + residual methyl oleate. A2 + dispersible oil suspension of bipyrazone (3+1) A2 + bipyrazone + 0.2% citric acid + 5% calcium dodecylbenzenesulfonate + 9% polyoxyethylene fatty alcohol ether + 6% castor oil polyoxyethylene ether + 2.5% organobentonite + 2 % fumed silica + 5% 100# solvent oil + balance methyl oleate 38. A2 + Dispersible Oil Suspension of Fenpyrazone (4+4) A2 + Fenpyrazone + 0.2% Citric Acid + 5% Calcium Dodecylbenzene Sulfonate + 9% Cardanol Polyoxyethylene Ether + 6% Castor Oil Polyoxyethylene Ether + 2.5% Organobentonite + 2 % fumed silica + 5% 100# solvent oil + balance methyl oleate 39. A2 + dispersible oil suspension of isoxaflutole (4+4) A2 + isoxaflutole + 0.3% citric acid + 5% calcium dodecylbenzenesulfonate + 9% polyoxyethylene fatty alcohol ether + 6% castor oil polyoxyethylene ether + 2 .5% organobentonite + 2% fumed silica + 5% 100# solvent oil + balance methyl oleate 40. A2+ dispersible oil suspension of clomazone (4+4) A2+ clomazone + 6% calcium dodecylbenzene sulfonate + 8% polyoxyethylene fatty alcohol ether + 7% castor oil polyoxyethylene ether + 2.5% organobentonite + 10% 100# solvent oil + residual methyl oleate 41 . Dispersible oil suspension of A2 + pyrazosulfuron-ethyl (4+2) A2 + pyrazosulfuron-ethyl + 0.5% urea + 5% calcium dodecylbenzenesulfonate + 7% polyoxyethylene fatty alcohol ether + 8% castor oil polyoxyethylene ether + 2.5% Organo bentonite + 2% fumed silica + 5% 100# solvent oil + balance methyl oleate 42. A2 + Dispersible Oil Suspension of Penoxsulam (4+1) A2 + Penoxsulam + 5% calcium dodecylbenzene sulfonate + 9% dehydrated sorbitol monooleate polyoxyethylene ether + 5% castor oil polyoxyethylene ether + 2.5% organobentonite + 2% fumed Silica + 5% 100# solvent oil + balance methyl oleate 43. A2 + dispersible oil suspension of imazamox (4+1) A2 + imazamox + 5% calcium dodecylbenzenesulfonate + 9% polyoxyethylene fatty alcohol ether + 5% castor oil polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 44. 100# solvent oil + residual methyl oleate. A2 + dispersible oil suspension of imazapic (4+1) A2 + imazapic + 5% calcium dodecylbenzenesulfonate + 9% polyoxyethylene fatty alcohol ether + 5% castor oil polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 5% 45. 100# solvent oil + residual methyl oleate. A2 + bispyribac-sodium (4+1) dispersible oil suspension A2 + bispyribac-sodium + 5% calcium dodecylbenzenesulfonate + 9% polyoxyethylene fatty alcohol ether + 5% castor oil polyoxyethylene ether + 2.5% organobentonite + 2% fume silica + 5% 100# solvent oil + residual methyl oleate 46. A2+ dispersible oil suspension of clethodim (4+2) A2+ clethodim + 5% calcium dodecylbenzene sulfonate + 9% polyoxyethylene fatty alcohol ether + 6% castor oil polyoxyethylene ether + 3% organobentonite + 2% fumed silica + 20% 100# Solvent oil + residual methyl oleate 47 . A2 + Dispersible Oil Suspension of Sethoxydim (4+2) A2 + Sethoxydim + 5% Calcium Dodecylbenzene Sulfonate + 9% Polyoxyethylene Fatty Alcohol Ether + 7% Castor Oil Polyoxyethylene Ether + 3% Organobentonite + 2% Fumed Silica + 6% 100# Solvent oil + residual methyl oleate 48 . Dispersible oil suspension of A2 + quizalofop-P-methyl (4+2) A2 + quizalofop-P-methyl + 5% calcium dodecylbenzenesulfonate + 8% polyoxyethylene fatty alcohol ether + 8% castor oil polyoxyethylene ether + 2.5% organo Bentonite + 2% fumed silica + 6% 100# solvent oil + residual methyl oleate 49. A2 + dispersible oil suspension of oxyfluorphen (3+1) A2 + oxyfluorphen + 5% calcium dodecylbenzene sulfonate + 8% cardanol polyoxyethylene ether + 6% castor oil polyoxyethylene ether + 3% organobentonite + 2% fumed silica + 20% 50. 100# solvent oil + residual methyl oleate. A2 + Dispersible Oil Suspension of Oxadiazone (3+1) A2 + Oxadiazone + 5% calcium dodecylbenzene sulfonate + 8% polyoxyethylene fatty alcohol ether + 6% castor oil polyoxyethylene ether + 3% organobentonite + 5% 100# solvent oil + balance of methyl oleate 51 . Dispersible oil suspension of A2 + oxadiargyl (3+1) A2 + oxadiargyl + 5% calcium dodecylbenzenesulfonate + 8% polyoxyethylene fatty alcohol ether + 6% castor oil polyoxyethylene ether + 2.5% organobentonite + 2% fumed silica + 15% 100# solvent oil + balance methyl oleate 52. A2 + suspension of atrazine (3+5) in water A2 + atrazine + 5% polycarboxylate + 2% phenylethylphenol polyoxyethylene ether phosphate triethanolamine salt + 0.22% xanthan gum + 2.2% magnesium aluminum silicate + 0.1% defoaming agent + 3% ethylene glycol + balance water 53. A2 + terbuthylazine (3+3) suspension in water A2 + terbuthylazine + 5% polycarboxylate + 2% phenylethylphenol polyoxyethylene ether phosphate triethanolamine salt + 0.26% xanthan gum + 2.2% aluminum magnesium silicate + 0.1% defoaming agent + 3% ethylene glycol + balance water 54. A2 + propanyl (2+20) suspension in water A2 + propanyl + 5% polycarboxylate + 2% phenylethylphenol polyoxyethylene ether phosphate triethanolamine salt + 0.18% xanthan gum + 1.8% magnesium aluminum silicate + 0.1% defoaming agent + 3% ethylene glycol + balance water 55. A2 + suspension of bentazone (4+30) in water A2 + bentazone + 5% polycarboxylate + 2% phenylethylphenol polyoxyethylene ether phosphate triethanolamine salt + 0.12% xanthan gum + 1.5% magnesium aluminum silicate + 0.1% defoaming agent + 3% ethylene glycol + balance water 56. A2 + Dispersible Oil Suspension of Butralin (4+21) A2 + Butralin + 10% Decanamide + 5% Calcium Dodecyl Benzene Sulfonate + 9% Polyoxyethylene Fatty Alcohol Ether + 7% Castor Oil Polyoxyethylene Ether + 1% Organobentonite + 1% Fumed Silica + 10 % 100# solvent oil + balance methyl oleate 57. A2 + dispersible oil suspension of pendimethalin (4+21) A2 + pendimethalin + 10% decanamide + 6% calcium dodecylbenzenesulfonate + 9% polyoxyethylene fatty alcohol ether + 5% castor oil polyoxyethylene ether + 1% organobentonite + 1% fumed silica + 10 % 100# solvent oil + balance methyl oleate 58. A2 + dispersible oil suspension of butachlor (4+6) A2 + butachlor + 6% calcium dodecylbenzene sulfonate + 9% cardanol polyoxyethylene ether + 7% castor oil polyoxyethylene ether + 3% organobentonite + 2% fumed silica + balance methyl oleate 59 . A2 + Dispersible Oil Suspension of Pretilachlor (2+4) A2 + Pretilachlor + 5% Calcium Dodecylbenzene Sulfonate + 9% Cardanol Polyoxyethylene Ether + 7% Castor Oil Polyoxyethylene Ether + 3% Organobentonite + 2% Fumed Silica + Remainder Methyl oleate 60 . Dispersible Oil Suspension of A2 + Anilophos (4+2) A2 + Anilophos + 5% calcium dodecylbenzene sulfonate + 9% polyoxyethylene fatty alcohol ether + 7% castor oil polyoxyethylene ether + 3% organobentonite + 2% fumed silica + 12% 100# Solvent oil + residual methyl oleate 61 . A2 + Dispersible Oil Suspension of Quinclolac (2+10) A2 + Quinclolac + 5% Calcium Dodecylbenzene Sulfonate + 9% Polyoxyethylene Fatty Alcohol Ether + 6% Castor Oil Polyoxyethylene Ether + 2.5% Organobentonite + 10% 100# Solvent Oil + residual methyl oleate 62 . A2 + Dispersible Oil Suspension of Fluoroxypyr (2+3) A2 + Fluoroxypyr + 5% Calcium Dodecylbenzene Sulfonate + 9% Phenylethylphenol Polyoxyethylene Ether + 6% Castor Oil Polyoxyethylene Ether + 3% Organobentonite + 3% Fumed Silica + 10% 100# solvent oil + balance methyl oleate 63. A2 + Dispersible Oil Suspension of Florpyraxifene Benzyl (3+1) A2 + Florpyroxifene Benzyl + 5% Calcium Dodecyl Benzene Sulfonate + 9% Polyoxyethylene Fatty Alcohol Ether + 6% Castor Oil Polyoxyethylene Ether + 3% Organobentonite + 2 % fumed silica + 12% 100# solvent oil + balance methyl oleate 64. Dispersible oil suspension of A2 + MCPA (3+10) A2 + MCPA + 6% calcium dodecylbenzene sulfonate + 9% polyoxyethylene fatty alcohol ether + 6% castor oil polyoxyethylene ether + 2% organobentonite + 1% fumed silica + 12% 100# solvent oil + residual methyl oleate 65 . A2 + Glyphosate (4+16) Suspension in Water A2 + Glyphosate + 5% Polycarboxylate + 2% Phenylethylphenol Polyoxyethylene Ether Phosphate Triethanolamine Salt + 3% Propylene Glycol Block Polyether + 0.2% Salt Tolerant Xanthan Gum + 1% Aluminum Silicate Magnesium + 0.1% defoamer + 3% ethylene glycol + balance water 66. A2 + Aqueous Suspension of Glufosinate Ammonium (3+15) A2 + Glufosinate Ammonium + 5% Polycarboxylate + 2% Phenylethylphenol Polyoxyethylene Ether Phosphate Triethanolamine Salt + 3% Propylene Glycol Block Polyether + 0.2% Salt Tolerant Xanthan Gum + 1% Silica 66. Magnesium aluminum acid + 0.1% defoamer + 3% ethylene glycol + balance water. A2 + dibromide dibromide dihydrate (4+15) suspension in water A2 + diquat dibromide monohydrate + 5% polycarboxylate + 2% phenylethylphenol polyoxyethylene ether phosphate triethanolamine salt + 3% propylene glycol 68. Block polyether + 0.2% salt tolerant xanthan gum + 1% magnesium aluminum silicate + 0.1% defoamer + 3% ethylene glycol + balance water. A2 + Dispersible Oil Suspension of Symmethylin (4+1) A2 + Symmethylin + 5% calcium dodecylbenzene sulfonate + 9% polyoxyethylene fatty alcohol ether + 6% castor oil polyoxyethylene ether + 3% organobentonite + 2% fumed silica + 10% 100# Solvent oil + residual methyl oleate.
上記の水懸濁液を処理するための装置:混合タンク、コロイドミル、サンドミルおよび剪断機等。 Equipment for processing the above water suspensions: mixing tanks, colloid mills, sand mills and shears, etc.
上記の水懸濁液を処理するためのプロセス:すべての材料を混合タンクに供給し、攪拌しながら混合し、コロイドミルに導入し、次いでサンドミルで3グレードの粉砕を行い、最後に剪断機で均一に剪断し、検査に合格した後、貯蔵タンクに移す。 Process for processing the above water suspension: All materials are fed into a mixing tank, mixed with stirring, introduced into a colloid mill, then sand milled to 3 grades, and finally sheared After it has been uniformly sheared and passed inspection, it is transferred to a storage tank.
上記の分散性油懸濁液を処理するための装置:混合タンク、コロイドミル、サンドミル、および剪断機等。 Equipment for processing the above dispersible oil suspensions: mixing tanks, colloid mills, sand mills, shears and the like.
上記の分散性油懸濁液を処理するプロセス:すべての材料を混合タンクに供給し、攪拌しながら混合し、コロイドミルに導入し、次いでサンドミルで3グレードの粉砕を行い、最後に剪断機で均一に剪断し、検査に合格した後、貯蔵タンクに移す。 Process of processing above dispersible oil suspension: All materials are fed into mixing tank, mixed with stirring, introduced into colloid mill, then sand milled to 3 grades, and finally sheared After it has been uniformly sheared and passed inspection, it is transferred to a storage tank.
B)有効性アッセイ
葉面散布による発芽後処理
1)実験条件
1.1)試験対象
シペルス・ディフォルミス(Cyperus difformis)は湖北省の荊州市で収集され、シペルス・イリア(Cyperus iria)は江西省の上饒市で収集され、モノコリア・バジナリス(Monochoria vaginalis)は湖南省の長沙市で収集され、エキノクロア・フィロポゴン(Echinochloa phyllopogon)は黒竜江省の撫遠市で収集され、サジタリア・トリフォリア(Sagittaria trifolia)は遼寧省の営口市で収集され、シルプス・ジュンコイデス(Scirpus juncoides)は黒竜江省の虎林市で収集され、ルードヴィヒア・プロストレート(Ludwigia prostrate)は湖南省の長沙市で採集され、ディジタリア・サングイナリス(Digitaria sanguinalis)は安徽省の天長市で収集され、アリスマ・プラントアゴ-アクアティカ(Alisma plantago-aquatica)は遼寧省の瀋陽市で収集された。上記の雑草を鉢植栽培法で栽培した。畑からの4/5の表土を含む180×140mmのプラスチック製の栄養ボウル(nutritional bowl)を、土壌を風乾してふるいにかけ、初期含水率を20%にしたエナメル製のパンに配置した。完全で均一な雑草の種子を選び、25℃の温水に6時間浸し、28℃の生化学的インキュベーター(暗闇)で発芽させた。発芽したばかりの雑草の種子を土の表面に均等に置き、趣旨の大きさに応じて0.5~1cmの土で覆った。
B) Efficacy assay Post-emergence treatment by foliar spraying 1) Experimental conditions 1.1) Test object Collected in Shangrao City, Monochoria vaginalis was collected in Changsha City, Hunan Province, Echinochloa phyllopogon was collected in Fuyuan City, Heilongjiang Province, and Sagittaria trifolia was collected in Liaoning Province. was collected in Yingkou, province, Scirpus juncoides was collected in Hulin, Heilongjiang, Ludwigia prostrate was collected in Changsha, Hunan, and Digitalia sanguinalis ( Digitaria sanguinalis was collected in Tianchang City, Anhui Province, and Alisma plantago-aquatica was collected in Shenyang City, Liaoning Province. The above weeds were cultivated by the pot culture method. A 180 x 140 mm plastic nutritional bowl containing 4/5 topsoil from the field was placed in an enamel pan where the soil was air dried, sieved and brought to an initial moisture content of 20%. Whole and uniform weed seeds were selected, soaked in warm water at 25°C for 6 hours and allowed to germinate in a biochemical incubator at 28°C (dark). Freshly germinated weed seeds were placed evenly on the surface of the soil and covered with 0.5-1 cm of soil depending on the intended size.
1.2)栽培条件
栽培は、制御可能な日光温室内、20~30℃、自然光および相対湿度57~72%で行った。土壌は、有機物含有量1.63%、pH値7.1、アルカリ加水分解性窒素84.3mg/kg、直ちに利用可能なリン38.5mg/kg、および直ちに利用可能なカリウム82.1mg/kgのロームであった。
1.2) Cultivation conditions Cultivation was carried out in a controlled sunlight greenhouse at 20-30°C, natural light and 57-72% relative humidity. The soil has an organic matter content of 1.63%, a pH value of 7.1, an alkaline hydrolyzable nitrogen of 84.3 mg/kg, a readily available phosphorus of 38.5 mg/kg and a readily available potassium of 82.1 mg/kg. was the ROHM of
1.3)機器および装置
3WP-2000型Walking Spray Tower(南京農業機械研究所、農業省);GA10型の10,000分の1電子天びん(ドイツ);ZDR2000型Intelligent Data Recorder(杭州ゼダインスツルメント製作所);およびSPXタイプのIntelligent Biochemical Incubator(寧波江南計器製作所)。
1.3) Instruments and Devices 3WP-2000 type Walking Spray Tower (Nanjing Agricultural Machinery Research Institute, Ministry of Agriculture); GA10 type 1/10,000 electronic balance (Germany); ZDR2000 type Intelligent Data Recorder (Hangzhou Zeda Instruments and SPX type Intelligent Biochemical Incubator (Ningbo Jiangnan Instrument Factory).
2)実験計画
2.1)試薬
必要な有効成分Aは特許CN201911014193.5に記載されているものであり、その具体的な調製プロセスは次のとおりである。
2) Experimental plan 2.1) Reagents The required active ingredient A is described in patent CN201911014193.5, and its specific preparation process is as follows.
(1)化合物A1の合成
(1.1)化合物1(3g、16mmol、1.0当量)、NaOH(0.72g、18mmol、1.1当量)を30mlのDMFに順次添加し、次いで化合物2(1.28g、16.8mmol、1.05当量)を0℃で滴下し、反応溶液を0℃で1時間攪拌した。LCMS試験で出発物質の反応がおおむね完了したことが示された時点で、1つの大きな新しいピークがあった。反応液を30mlの水に注ぎ、混合物を分離し、水相を50mlの酢酸エチルで1回抽出し、得られた有機相を飽和食塩水(50ml)で3回洗浄し、乾燥させ、減圧下で蒸発乾固し、カラムクロマトグラフィーにより分離して、化合物3(3.6g、91%の収率)(無色の油)を得た。
(1.2)化合物3(3.1g、13mmol、1.0当量)を30mlのTHFに添加し、次いでn-BuLi(6.42ml、2.5M、16mmol、1.2当量)を-78℃でゆっくりと添加し、次いで反応溶液を-78℃で0.5時間攪拌し、CO2を10分間ゆっくりと供給し、次いで反応溶液をゆっくりと室温に温めた。生成物をLCMSによって検出した。反応溶液に水20mlを注ぎ、混合物を分離し、水相を酢酸エチル30mlで1回抽出し、得られた水相を濃塩酸で徐々にpH=4~5に調整し、濾過し、乾燥させて化合物4(3.2g、87%収率)(白色固体)を得た。
(1.3)化合物4(3.1g、11mmol、1.0当量)、化合物5(1.66g、16.8mmol、1.5当量)、DMAP(0.13g、1.1mmol、0.1当量)を30mlのピリジンに順次添加した。次いで、SOCl2(2.0g、16.8mmol、1.5当量)を0℃でゆっくりと添加し、反応溶液を室温で3時間攪拌した。生成物をLCMSによって検出した。ピリジンを濃縮除去した後、30mlの水を反応液に注ぎ、混合物を分離した。水相を酢酸エチル30mlで3回抽出し、得られた有機相を飽和食塩水(50ml)で3回洗浄し、乾燥し、減圧下で蒸発乾固し、カラムクロマトグラフィーで分離して化合物6(2.5g、63%収率)(白色固体)を得た。
(1.4)化合物6(1g、2.8mmol、1.0当量)およびm-CPBA(0.54g、3.1mmol、1.1当量)を10mLのジクロロメタンに順次添加した。次いで、反応溶液を室温で1時間攪拌した。生成物をLCMSで検出し、原料の反応をおおむね完了させた。反応溶液を10mlの水に注ぎ、亜硫酸水素ナトリウムで反応を停止させ、混合物を分離した。水相をジクロロメタン30mlで3回抽出し、得られた有機相を飽和食塩水(30ml)で1回洗浄し、乾燥し、減圧下で蒸発乾固し、カラムクロマトグラフィーで分離して化合物A1(0.85g、82%収率)(灰白色の固体)を得た。
1H NMR (500 MHz, DMSO-d6) 12.57 (s, 1H), 8.07 (dd, J = 8.0, 7.0 Hz, 1H), 7.82 (d, J = 8.0 Hz, 1H), 3.57-3.47 (m, 2H), 2.48 (s, 3H), 1.70-1.52 (m, 2H), 1.08-0.93 (m, 3H).
1 H NMR (500 MHz, DMSO-d 6 ) 12.57 (s, 1H), 8.07 (dd, J = 8.0, 7.0 Hz, 1H), 7.82 (d, J = 8.0 Hz, 1H), 3.57-3.47 (m , 2H), 2.48 (s, 3H), 1.70-1.52 (m, 2H), 1.08-0.93 (m, 3H).
(2)化合物A2の合成
化合物A1(0.5g、純度98%)をキラルHPLC(カラム:CHIRALPAK IG;カラムサイズ:3cm×25cm、5μm;注入:3.0ml;移動相:Hex(0.2%FA):IPA=50:50;流量:28ml/分;波長:UV254nm;温度:25℃;サンプル溶液:EtOH/DCM中70mg/ml;分析時間=60分)を通して分離した後、濃縮して、単結晶回折により確認される化合物A2(R-配置)を白色固体として得た(0.16g、Rt=10.51分、100% ee、純度98%)。
有効成分B、例えばシピラフルオン、ビピラゾン、フェンピラゾン、トリピラスルホン、
ここで、
(1)化合物a(0.5g、2.13mmol)、化合物b(313mg、2.55mmol)、触媒量のTBAB(10mg)およびDMF(10mL)を丸底フラスコに入れ、室温15℃で24時間攪拌した。LC-MS検出により少量の出発物質が残っている場合、さらなる処理を行った。反応溶液を50mLの水に注ぎ、メチルtert-ブチルエーテルで2回抽出した(50mL×2)。有機相を乾燥させ、濃縮し、カラムクロマトグラフィーにより分離して、化合物c(300mg、収率50%)を白色の固体として得た。
(2)化合物c(0.3g、1.06mmol)、メタノール(20mL)を100mLシングルポートフラスコに入れ、水酸化リチウム(44.5mg、1.06mmol)を2mLの水に溶解し、室温で12時間シングルポートフラスコにゆっくりと滴下し、次いで室温で12時間攪拌した。LC-MS検出により出発物質の反応が完了した後、反応溶液を0.5M希HClでpH=5~6に調整し、濃縮し、次いで水および酢酸エチルで抽出した。有機相を乾燥し、濃縮して、化合物d(200mg、収率70%)を白色の固体として得た。
(3)化合物d(200mg、0.74mmol)、化合物e(75mg、0.74mmol)、DCC(152mg、0.74mmol)、無水DCM(20mL)を100mL丸底フラスコに入れ、室温で12時間反応させた。LC-MS検出による出発物質の反応が完了した後、反応溶液を濃縮し、カラムクロマトグラフィーによって分離して、標的化合物(200mg、収率77%)を白色固体として得た。
2.2)実験的処理
2.2.1)用量の決定
各グループにおける有効成分Aと有効成分Bとの比率およびそれらの量は、2つの薬剤の特性および毒性、ならびに対応する製剤の主な用途による。この研究の事前試験に基づいて、単独および組み合わせで適用された有効成分AおよびBの用量を表に示す。上記のグループと同じ溶媒および乳化剤を含むが、薬剤を含まない水をブランク対照として用いた。
2.2) Experimental Treatment 2.2.1) Dose Determination Depends on usage. The doses of active ingredients A and B applied alone and in combination, based on pre-tests for this study, are shown in the table. Water containing the same solvent and emulsifier as the above group, but without drug was used as a blank control.
2.2.2)実験の反復
ポットあたり20個の雑草種子を含む3個のポットを、1回の処理につき4回の複製で処理した。すなわち、1回の処理で合計60の雑草が処理された。
2.2.2) Replicate experiment Three pots containing 20 weed seeds per pot were treated with four replications per treatment. Thus, a total of 60 weeds were treated in one treatment.
2.3)処理方法
2.3.1)処理のタイミングおよび頻度
実験では、薬剤は1回だけ用いられた。1~1.5葉の雑草の段階では、雑草を間引いて1ポットあたり15雑草、各処理で45雑草を維持し、次いで2~3葉の段階まで栽培して処理した。
2.3) Treatment method 2.3.1) Timing and frequency of treatment In the experiment, the drug was used only once. At the 1-1.5 leaf weed stage, the weeds were thinned to maintain 15 weeds per pot, 45 weeds per treatment, then grown to the 2-3 leaf stage and treated.
2.3.2)薬剤を適用するための機器および方法
十分に栽培された雑草を面積0.5m2の台に均等に置き、3WP-2000型Walking Spray Towerにより450kg/haの用量および0.3MPaのスプレー圧力で薬剤溶液を茎および葉に噴霧した。すべての溶液が噴霧された後、バルブを閉じた。30秒後、スプレー塔の扉を開き、栄養ボウルを取り出した。次いで、バルブを開き、50mlの水を噴霧してスプレーチューブを洗浄した。
2.3.2) Equipment and Methods for Applying the Agents Well cultivated weeds were placed evenly on a platform with an area of 0.5 m 2 and sprayed with a 3WP-2000 type Walking Spray Tower at a dosage of 450 kg/ha and 0.5 m 2 . The drug solution was sprayed onto the stems and leaves with a spray pressure of 3 MPa. After all the solution was nebulized, the valve was closed. After 30 seconds, the spray tower door was opened and the nutrition bowl was removed. The valve was then opened and 50 ml of water was sprayed to clean the spray tube.
3)実験方法
鉢植栽培法により行った。雑草の栽培については、1.1)の項および“Pesticide guidelines for laboratory bioactivity tests - herbicides”を参照されたい。薬剤の適用方法については、2.3.2)の項、すなわち葉面処理を参照されたい。処理後、雑草を温室で通常の通りに栽培した。
3) Experimental method It was carried out by the pot culture method. For weed cultivation see section 1.1) and “Pesticide guidelines for laboratory bioactivity tests - herbicides”. For the method of applying the drug, see section 2.3.2), foliar treatment. After treatment, weeds were grown as usual in the greenhouse.
4)データ調査および統計分析
4.1)調査方法
絶対数を調べる方法が用いられ、生存雑草の実生全体を土壌表面に沿って刃で切り取り、雑草の新鮮重量を分析天秤で秤量した。枯れた雑草の場合、その新鮮重量はゼロとした。
4) Data Survey and Statistical Analysis 4.1) Survey Method A method of determining absolute numbers was used, whole seedlings of surviving weeds were cut along the soil surface with a blade and the fresh weight of the weeds was weighed on an analytical balance. For dead weeds, the fresh weight was taken as zero.
4.2)調査のタイミングおよび頻度
調査は、15日間の処理後に1回だけ行った。
4.2) Timing and Frequency of Surveys Surveys were performed only once after 15 days of treatment.
4.3)データの統計分析
各グループの2つの有効成分の組み合わせの理論上の新鮮重量抑制率をGowing法(E0=X+Y-X*Y/100)で計算し、次いで、実際に測定された抑制率(E)と比較して、雑草に対する組み合わせの効果(以下、組み合わせ効果という)を評価した:E-E0の値が10%を超える場合は相乗効果に対応し、E-E0の値が-10%未満の場合は拮抗効果に対応し、E-E0の値が-10~10%の場合は不可的効果に対応するものとした。2つの有効成分の最適な比率は、実際の防除効果、除草剤の特性、および対応する処方のバランスによって決定された。ここで、式において、Xは、Pの用量における有効成分Aの新鮮重量阻害率を表し、Yは、Qの用量における有効成分Bの新鮮重量阻害率を表す。
4.3) Statistical Analysis of Data The theoretical fresh weight inhibition rate of each group of two active ingredient combinations was calculated by the Gowing method (E0=X+Y−X*Y/100) and then measured in practice. The effect of the combination on weeds (hereinafter referred to as combination effect) was evaluated in comparison with the control rate (E): E-E0 values greater than 10% corresponded to synergistic effects, E-E0 values A value of less than -10% corresponded to an antagonistic effect, and an E-E0 value of -10 to 10% corresponded to an unfavorable effect. The optimum ratio of the two active ingredients was determined by a balance of actual control efficacy, herbicide properties and corresponding formulations. where X represents the fresh weight inhibition rate of active ingredient A at P dose and Y represents the fresh weight inhibition rate of active ingredient B at Q dose.
統計結果を以下の表1~223に示す。 The statistical results are shown in Tables 1-223 below.
C)試験用地
実施例1~68で調製された除草用組成物を用いて野外の雑草を防除した試験である。
C) Test site This is a test in which the herbicidal compositions prepared in Examples 1-68 were used to control weeds in the field.
2017年には、江西省の番陽県(Poyang City)の試験用地において、実証普及試験(demonstration popularization test)が行われた。畑の雑草には、主にエキノクロア・クルス-ガリ(Echinochloa crus-galli)、レプトクロア・キネンシス(Leptochloa chinensis)、モノコリア・バジナリス(Monochoria vaginalis)、シペルス・ディフォルミス(Cyperus difformis)、ルードヴィヒア・プロストレート(Ludwigia prostrate)等が含まれていた。 In 2017, a demonstration popularization test was conducted at a pilot site in Poyang City, Jiangxi Province. Field weeds mainly include Echinochloa crus-galli, Leptochloa chinensis, Monochoria vaginalis, Cyperus difformis, Ludwigia prostrate ( Ludwigia prostrate) and others were included.
実験方法:
葉面処理:雑草の葉が2~3枚葉の段階で、手動噴霧器を用いて薬剤を茎および葉に均等に噴霧し、添加水量は30kg/667m2とした。
experimental method:
Foliar treatment: When the weeds had 2 to 3 leaves, the chemicals were evenly sprayed on the stems and leaves using a manual sprayer, and the amount of water added was 30 kg/667 m 2 .
具体的な試験薬剤およびその投与量を表224に示す。試験用地の面積は20平方メートルであり、各処理を3回繰り返した。20日間の適用後の雑草の防除効率を表224に示す。 Specific study agents and their dosages are shown in Table 224. The area of the test site was 20 square meters and each treatment was repeated three times. The weed control efficiency after 20 days of application is shown in Table 224.
広範な実験および調査を行った結果、本発明者らは、本発明の組成物が、シペルス・ディフォルミス(Cyperus difformis)、シペルス・イリア(Cyperus iria)、モノコリア・バジナリス(Monochoria vaginalis)、エキノクロア・フィロポゴン(Echinochloa phyllopogon)、サジタリア・トリフォリア(Sagittaria trifolia)、シルプス・ジュンコイデス(Scirpus juncoides)、ルードヴィヒア・プロストレート(Ludwigia prostrate)、ディジタリア・サングイナリス(Digitaria sanguinalis)、アリスマ・プラントアゴ-アクアティカ(Alisma plantago-aquatica)、エキノクロア・クルス-ガリ(Echinochloa crus-galli)、レプトクロア・キネンシス(Leptochloa chinensis)等の雑草を防除するために用いられること、驚くべき予期せぬ相乗効果が達成されること、低用量でも相乗効果が特に顕著であること、それによって適用量が低減され、環境汚染が低減されることを、合理的な配合により農業コストが削減され、ALSおよびACCaseの阻害剤に対して抵抗性の雑草を極めて高い防除がもたらされることを予期せず見出した。本発明の組成物は、良好な適用可能性を有している。同時に、本発明の組成物が、コムギ畑、トウモロコシ畑およびコメ畑等の畑において、ならびにピーナッツ、サトウキビ、ソルガム、キビ、ジャガイモ、ナタネ、ダイズ、ワタ、野菜、一年生のブルーグラス、ヒロハノウシノケグサおよびゾシア・ジャポニカ(Zoysia japonica)等の作物に対して良好な選択性および優れた相乗効果を奏すること、および幅広い市場価値を有する除草剤配合物に開発され得ることが実験によって示された。 After extensive experiments and investigations, the inventors have found that the compositions of the present invention are effective against Cyperus difformis, Cyperus iria, Monochoria vaginalis, Echinoclora filopogon (Echinochloa phyllopogon), Sagittaria trifolia, Scirpus juncoides, Ludwigia prostrate, Digitaria sanguinalis, Alisma plantago -aquatica), Echinochloa crus-galli, Leptochloa chinensis, etc. Surprising and unexpected synergistic effect achieved, low dosage However, the synergistic effect is particularly pronounced, resulting in reduced dosage and reduced environmental pollution, rational formulation reduces agricultural costs, and resistance to inhibitors of ALS and ACCase. It has been unexpectedly found that very high control of weeds is provided. The composition of the invention has good applicability. At the same time, the compositions of the present invention can be used in fields such as wheat fields, corn fields and rice fields, as well as peanuts, sugar cane, sorghum, millet, potatoes, rapeseed, soybeans, cotton, vegetables, annual bluegrass, fescue and Experiments have shown that it has good selectivity and good synergistic effect on crops such as Zoysia japonica and can be developed into herbicide formulations with broad market value.
Claims (10)
前記有効成分Aが
前記有効成分Bが、以下の1種以上の化合物またはその塩もしくはエステルから選択される、前記除草用組成物:
(1)スルコトリオン、メソトリオン、トプラメゾン、テンボトリオン、ビシクロピロン、テフリルトリオン、ベンゾビシロン、ビピラゾン、シピラフルオン、トリピラスルホン、フェンピラゾン、ピラスルホトール、ピラゾリネート、ベンゾフェナプ、トルピラレート、フェンキノトリオン、イソキサフルトール、ピラゾキシフェンおよび
(2)フルロクロリドン、フルルタモン、ジフルフェニカン、ピコリナフェン、ベフルブタミド、ノルフルラゾンおよびフルリドンから選択されるPDS阻害剤;
(3)クロマゾンおよびビクスロゾンから選択されるDOXP阻害剤;
(4)トリベヌロン-メチル、チフェンスルフロンメチル、ベンスルフロンメチル、ピラゾスルフロン-エチル、チエンカルバゾン-メチル、ハロスルフロンメチル、プロピリスルフロン、メタゾスルフロン、リムスルフロン、エトキシスルフロン、オルトスルファムロン、フルカルバゾン-ナトリウム、メソスルフロン-メチル、ニコスルフロン、ホラムスルフロン、フルメツラム、トリアファモン、ペノキススラム、クロランスラム-メチル、ピロキススラム、イマザモックス、イマザピック、イマザピル、ピリミノバック-メチル、フロラスラム、ピリフタリド、ピリベンゾキシム、プロカルバゾンナトリウム、イマゼタピル、クロルスルフロン、シノスルフロン、シクロスルファムロン、アミドスルフロン、トリアスルフロン、ヨードスルフロンメチルナトリウム、フルピルスルフロン-メチルナトリウム、フルセトスルフロン、メツルフロンメチル、トリトスルフロン、スルホスルフロン、イマゾスルフロン、ビスピリバック-ナトリウムおよびメトスラムから選択されるALS阻害剤;
(5)クロジナホップ-プロパルギル、ピノキサデン、クレトジム、セトキシジム、キザロホップ-P-メチル、トラルコキシジム、フルアジホップ-ブチル、ハロキシホップ-P-メチル、ジクロホップ-メチル、フェノキサプロップ-P-エチル、シハロホップ-ブチル、プロホキシジム、メタミホップおよびプロパキザホップから選択されるACCase阻害剤;
(6)オキシフルオルフェン、フォメサフェン、オキサジアゾン、オキサジアルギル、スルフェントラゾン、ピラクロニル、フルミオキサジン、ペントキサゾン、チアフェナシル、サフルフェナシル、ピラフルフェン-エチル、カルフェントラゾン-エチル、ブタフェナシル、エトキシフェン-エチル、フルオログリコフェン、アシフルオルフェン-ナトリウム、トリフルジモキサジン、フルチアセット-メチルおよびエピリフェナシルから選択されるPPO阻害剤;
(7)アトラジン、プロミトリン、シメトリン、テルブチラジン、テルブトリン、アメトリン、ジプロペトリン、ランバスト、デスメトリン、シマジン、メトリブジン、エチオジン、アミカルバゾン、メタミトロン、シアナジン、クロロトルロン、イソプロツロン、ジウロン、フルオメツロン、リヌロン、テブチウロン、ダイムロン、モノリヌロン、メトブロムロン、ネブロン、ピリダフォル、ヘキサジノン、ジメタメトリン、トリエタジン、ブロマシル、レナシル、テルバシル、メタベンズチアズロン、シズロン、イソウロン、メトクスロン、クロロクスロン、トリフルジモキサジン、シクロピリモレート、プロパニル、ピリデート、デスメジファム、フェンメジファム、ベンタゾン、オクタン酸ブロモキシニル、ブロモキシニルおよびイソキシニルから選択されるPSII阻害剤;
(8)トリフルラリン、ブトラリン、ペンジメタリン、ジチオピル、エタルフルラリン、オリザリン、ベンフルラリン、チアゾピル、プロピザミド、ダクタールおよびブタミホスから選択される微小管集合阻害剤;
(9)微小管組織化阻害剤であるカルベタミド;
(10)アセトクロール、ブタクロール、プレチラクロール、メトラクロール、メフェナセット、s-メトラクロール、フルフェナセット、ナプロパミド、ピロキサスルホン、アニロホス、ジメテナミド、フェントラザミド、イプフェンカルバゾン、カフェントロール、ピペロホス、プロピソクロール、アラクロール、メタザクロール、プロパクロール、ペトキサミド、ジメスルファゼットおよびフェノキサスルホンから選択されるVLCFA阻害剤;
(11)プロスルホカルブ、モリネート、ベンチオカルブ、ベンフレセート、エトフメセート、トリアレート、ベルノレート、ブチレート、シクロエート、ジメピペレートおよびエスプロカルブから選択される脂質合成(非アセチルCoAカルボキシラーゼ)阻害剤;
(12)キンクロラック、フルロキシピル、フルロキシピルメプチル、ハロキシフェン-メチル、トリクロピル、クロピラリド、ピクロラム、アミノピラリド、ジカンバ、フロルピラキシフェンベンジル、MCPA、MCPA-チオエチル、MCPB、2-(2-メチル-4-クロロフェノキシ)プロピオン酸、2-(4-クロロ-2-メチルフェノキシ)酢酸ナトリウム、(2-メチル-4-クロロフェノキシ)酢酸イソオクチル、2,4-ジクロロフェノキシ酢酸ブチル、2,4-ジクロロフェノキシ酢酸イソオクチル、2,4-ジクロロフェノキシ酢酸、キンメラック、MCPAジメチルアンモニウム塩、2-(2,4-ジクロロフェノキシル)プロピオン酸、2,4-ジクロロフェノキシ酪酸、ベナゾリン-エチル、アミノシクロピラクロール、
(13)グリホセートおよびスルホセートから選択されるEPSPS阻害剤;
(14)グルホシネートアンモニウム、ビアラホスおよびグルホシネート-P-アンモニウムから選択されるGS阻害剤;
(15)パラコート二塩化物およびジクワットジブロミド一水和物から選択されるPSI阻害剤;
(16)DHP阻害剤であるアスラム;
(17)トリアジフラムおよびインダジフラムから選択されるセルロース合成阻害剤;
(18)オキサジクロメフォン、シンメチリン、インダノファン、ジクロロキノリノン、クイカオトン、クミルロン、モヌロンおよびテトフルピロリメットから選択されるその他のもの。 A herbicidal composition comprising an N-(1,3,4-oxadiazol-2-yl)arylcarboxamide compound, comprising active ingredient A and active ingredient B in herbicidally effective amounts,
The active ingredient A is
The herbicidal composition, wherein the active ingredient B is selected from one or more of the following compounds or salts or esters thereof:
(1) sulcotrione, mesotrione, topramezone, tembotrione, bicyclopyrone, tefuryltrione, benzovicilone, bipyrazone, cipirafluone, tripyrasulfone, fenpyrazone, pyrasulfotole, pyrazolinate, benzofenap, tolpiralate, fenquinotrione, isoxaflutole , pyrazoxifene and
(2) a PDS inhibitor selected from flurochloridone, flurutamone, diflufenican, picolinafen, beflubutamide, norflurazone and fluridone;
(3) a DOXP inhibitor selected from clomazone and bixrozone;
(4) tribenuron-methyl, thifensulfuron-methyl, bensulfuron-methyl, pyrazosulfuron-ethyl, thiencarbazone-methyl, halosulfuron-methyl, propyrisulfuron, metazosulfuron, rimsulfuron, ethoxysulfuron, orthosulfamuron, flucarbazone-sodium, mesosulfuron-methyl, nicosulfuron, foramsulfuron, flumetsulam, triafamone, penoxsulam, cloransulam-methyl, piroxsulam, imazamox, imazapic, imazapyr, pyriminobac-methyl, florasulam, pyriftalide, pyribenzoxime, procarbazone sodium, imazethapyr, chlorsulfuron, Cinosulfuron, cyclosulfamuron, amidosulfuron, triasulfuron, iodosulfuron-methyl sodium, flupyrsulfuron-methyl sodium, flucetosulfuron, metsulfuron-methyl, tritosulfuron, sulfosulfuron, imazosulfuron, bispyribac-sodium and metsulam an ALS inhibitor selected from;
(5) clodinafop-propargyl, pinoxaden, clethodim, sethoxydim, quizalofop-P-methyl, tralcoxydim, fluazifop-butyl, haloxyfop-P-methyl, diclofop-methyl, fenoxaprop-P-ethyl, cyhalofop-butyl, profoxydim, metamifop and an ACCase inhibitor selected from propaquizafop;
(6) oxyfluorfen, fomesafen, oxadiazone, oxadiargyl, sulfentrazone, pyraclonil, flumioxazin, pentoxazone, thiaphenacil, saflufenacil, pyraflufen-ethyl, carfentrazone-ethyl, butaphenacil, ethoxyfen-ethyl, fluoroglycofen, a PPO inhibitor selected from acifluorfen-sodium, trifludimoxazine, fluthiacet-methyl and epirifenacil;
(7) atrazine, promitrin, simetryn, terbuthylazine, terbutrin, ametrine, dipropethrin, lambast, desmethrin, simazine, metribuzine, ethiodine, amicarbazone, metamitron, cyanazine, chlorotoluron, isoproturon, diuron, fluomethuron, linuron, tebuthiuron, daimuron, monolinuron, metobromuron , nevron, pyridafol, hexazinone, dimethamethrin, trietadine, bromacil, renacil, terbacil, metabenzthiazuron, cizuron, isouron, metoxuron, chloroxuron, trifludimoxazine, cyclopyrimolate, propanil, pyridate, desmedifam, fenmedifam , bentazone, bromoxynil octanoate, bromoxynil and isoxynil;
(8) microtubule assembly inhibitors selected from trifluralin, butralin, pendimethalin, dithiopyr, ethalfluralin, oryzalin, benfluralin, thiazopyr, propyzamide, dactal and butamifos;
(9) Carbetaamide, a microtubule assembly inhibitor;
(10) acetochlor, butachlor, pretilachlor, metolachlor, mefenacet, s-metolachlor, flufenacet, napropamide, pyroxasulfone, anilophos, dimethenamide, fentrazamide, ipfencarbazone, caffenchol, piperophos, propisochlor, a VLCFA inhibitor selected from alachlor, metazachlor, propachlor, petoxamide, dimesulfazet and phenoxasulfone;
(11) lipid synthesis (non-acetyl CoA carboxylase) inhibitors selected from prosulfocarb, molinate, benchocarb, benfuresate, ethofumesate, trialate, vernolate, butyrate, cycloate, dimepiperate and esprocarb;
(12) quinclolac, fluroxypyr, fluroxypyrmeptyl, haloxifene-methyl, triclopyr, clopyralid, picloram, aminopyralid, dicamba, florpyraxifenebenzyl, MCPA, MCPA-thioethyl, MCPB, 2-(2-methyl-4) -chlorophenoxy)propionic acid, sodium 2-(4-chloro-2-methylphenoxy)acetate, isooctyl (2-methyl-4-chlorophenoxy)acetate, butyl 2,4-dichlorophenoxyacetate, 2,4-dichlorophenoxy isooctyl acetate, 2,4-dichlorophenoxyacetic acid, quinmerac, MCPA dimethylammonium salt, 2-(2,4-dichlorophenoxyl)propionic acid, 2,4-dichlorophenoxybutyric acid, benazolin-ethyl, aminocyclopyrachlor,
(13) an EPSPS inhibitor selected from glyphosate and sulfosate;
(14) a GS inhibitor selected from glufosinate-ammonium, bialaphos and glufosinate-P-ammonium;
(15) a PSI inhibitor selected from paraquat dichloride and diquat dibromide monohydrate;
(16) Aslam, a DHP inhibitor;
(17) a cellulose synthesis inhibitor selected from triaziflam and indaziflam;
(18) Others selected from oxadichromefone, cymmethylin, indanophane, dichloroquinolinone, quicaotone, cumyluron, monuron and tetoflupyrrolimet.
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CN201911045226.2 | 2019-10-30 | ||
CN202010953693.1A CN112741097B (en) | 2019-10-30 | 2020-09-11 | Herbicidal compositions comprising N- (1, 3, 4-oxadiazol-2-yl) arylcarboxamides and their use |
CN202010953693.1 | 2020-09-11 | ||
PCT/CN2020/124587 WO2021083245A1 (en) | 2019-10-30 | 2020-10-29 | Herbicidal composition comprising n-(1,3,4-oxadiazole-2-yl)arylformamide compound and use thereof |
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CN113615694A (en) * | 2021-08-24 | 2021-11-09 | 青岛恒宁生物科技有限公司 | Weeding composition containing protoporphyrinogen oxidase inhibitor and application thereof |
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UA116532C2 (en) * | 2011-12-13 | 2018-04-10 | Байєр Інтеллектуал Проперті Гмбх | N-(1,2,5-oxadiazol-3-yl)-, n-(1,3,4-oxadiazol-2-yl)-, n-(tetrazol-5-yl)- und n-(triazol-5-yl)-arylcarbonsaureamide und ihre verwendung als herbizide |
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