CZ303977B6 - Herbicidní prostredek s acylovanými aminofenylsulfonylmocovinami a zpusob hubení skodlivých rostlin - Google Patents
Herbicidní prostredek s acylovanými aminofenylsulfonylmocovinami a zpusob hubení skodlivých rostlin Download PDFInfo
- Publication number
- CZ303977B6 CZ303977B6 CZ20010557A CZ2001557A CZ303977B6 CZ 303977 B6 CZ303977 B6 CZ 303977B6 CZ 20010557 A CZ20010557 A CZ 20010557A CZ 2001557 A CZ2001557 A CZ 2001557A CZ 303977 B6 CZ303977 B6 CZ 303977B6
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- CZ
- Czechia
- Prior art keywords
- plants
- methyl
- compounds
- group
- herbicides
- Prior art date
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- 239000004009 herbicide Substances 0.000 title claims abstract description 67
- 238000000034 method Methods 0.000 title claims abstract description 26
- -1 aminophenylsulfonyl ureas Chemical class 0.000 title description 72
- 235000013877 carbamide Nutrition 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 98
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 97
- 150000003839 salts Chemical class 0.000 claims abstract description 71
- 241000196324 Embryophyta Species 0.000 claims description 137
- 239000013543 active substance Substances 0.000 claims description 94
- 239000000203 mixture Substances 0.000 claims description 60
- 240000008042 Zea mays Species 0.000 claims description 58
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 58
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 55
- 235000009973 maize Nutrition 0.000 claims description 55
- 238000009472 formulation Methods 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 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 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 235000013339 cereals Nutrition 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 7
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000005574 MCPA Substances 0.000 claims description 6
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 claims description 6
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 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
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 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 6
- PFJJMJDEVDLPNE-UHFFFAOYSA-N Benoxacor Chemical compound C1=CC=C2N(C(=O)C(Cl)Cl)C(C)COC2=C1 PFJJMJDEVDLPNE-UHFFFAOYSA-N 0.000 claims description 5
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 claims description 4
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 claims description 4
- 239000005476 Bentazone Substances 0.000 claims description 4
- 239000005504 Dicamba Substances 0.000 claims description 4
- YLPGTOIOYRQOHV-UHFFFAOYSA-N Pretilachlor Chemical compound CCCOCCN(C(=O)CCl)C1=C(CC)C=CC=C1CC YLPGTOIOYRQOHV-UHFFFAOYSA-N 0.000 claims description 4
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 claims description 4
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 claims description 4
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 claims description 4
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 4
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- LNGRZPZKVUBWQV-UHFFFAOYSA-N (4-chloro-2-methylsulfonylphenyl)-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CS(=O)(=O)C1=CC(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 LNGRZPZKVUBWQV-UHFFFAOYSA-N 0.000 claims description 3
- RBSXHDIPCIWOMG-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea Chemical compound CCS(=O)(=O)C=1N=C2C=CC=CN2C=1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 RBSXHDIPCIWOMG-UHFFFAOYSA-N 0.000 claims description 3
- GOCUAJYOYBLQRH-UHFFFAOYSA-N 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-UHFFFAOYSA-N 0.000 claims description 3
- JLYFCTQDENRSOL-UHFFFAOYSA-N 2-chloro-N-(2,4-dimethylthiophen-3-yl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound COCC(C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-UHFFFAOYSA-N 0.000 claims description 3
- ABOOPXYCKNFDNJ-UHFFFAOYSA-N 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 claims description 3
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 claims description 3
- 239000003666 Amidosulfuron Substances 0.000 claims description 3
- CTTHWASMBLQOFR-UHFFFAOYSA-N Amidosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)N(C)S(C)(=O)=O)=N1 CTTHWASMBLQOFR-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 239000005489 Bromoxynil Substances 0.000 claims description 3
- WMLPCIHUFDKWJU-UHFFFAOYSA-N Cinosulfuron Chemical compound COCCOC1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=NC(OC)=N1 WMLPCIHUFDKWJU-UHFFFAOYSA-N 0.000 claims description 3
- 239000005500 Clopyralid Substances 0.000 claims description 3
- BXEHUCNTIZGSOJ-UHFFFAOYSA-N Esprocarb Chemical compound CC(C)C(C)N(CC)C(=O)SCC1=CC=CC=C1 BXEHUCNTIZGSOJ-UHFFFAOYSA-N 0.000 claims description 3
- UWVKRNOCDUPIDM-UHFFFAOYSA-N Ethoxysulfuron Chemical compound CCOC1=CC=CC=C1OS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 UWVKRNOCDUPIDM-UHFFFAOYSA-N 0.000 claims description 3
- QZXATCCPQKOEIH-UHFFFAOYSA-N Florasulam Chemical compound N=1N2C(OC)=NC=C(F)C2=NC=1S(=O)(=O)NC1=C(F)C=CC=C1F QZXATCCPQKOEIH-UHFFFAOYSA-N 0.000 claims description 3
- 239000005561 Glufosinate Substances 0.000 claims description 3
- 239000005562 Glyphosate Substances 0.000 claims description 3
- LXKOADMMGWXPJQ-UHFFFAOYSA-N Halosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=C(Cl)C=2C(O)=O)C)=N1 LXKOADMMGWXPJQ-UHFFFAOYSA-N 0.000 claims description 3
- XVOKUMIPKHGGTN-UHFFFAOYSA-N Imazethapyr Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 XVOKUMIPKHGGTN-UHFFFAOYSA-N 0.000 claims description 3
- 239000005567 Imazosulfuron Substances 0.000 claims description 3
- NAGRVUXEKKZNHT-UHFFFAOYSA-N Imazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N3C=CC=CC3=NC=2Cl)=N1 NAGRVUXEKKZNHT-UHFFFAOYSA-N 0.000 claims description 3
- SUSRORUBZHMPCO-UHFFFAOYSA-N MC-4379 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 SUSRORUBZHMPCO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005578 Mesotrione Substances 0.000 claims description 3
- 239000005583 Metribuzin Substances 0.000 claims description 3
- 239000005586 Nicosulfuron Substances 0.000 claims description 3
- 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 3
- 239000005591 Pendimethalin Substances 0.000 claims description 3
- LTUNNEGNEKBSEH-UHFFFAOYSA-N Prosulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)CCC(F)(F)F)=N1 LTUNNEGNEKBSEH-UHFFFAOYSA-N 0.000 claims description 3
- 239000005606 Pyridate Substances 0.000 claims description 3
- JTZCTMAVMHRNTR-UHFFFAOYSA-N Pyridate Chemical compound CCCCCCCCSC(=O)OC1=CC(Cl)=NN=C1C1=CC=CC=C1 JTZCTMAVMHRNTR-UHFFFAOYSA-N 0.000 claims description 3
- 239000005616 Rimsulfuron Substances 0.000 claims description 3
- 239000005618 Sulcotrione Substances 0.000 claims description 3
- 239000005627 Triclopyr Substances 0.000 claims description 3
- HFEJHAAIJZXXRE-UHFFFAOYSA-N cafenstrole Chemical compound CCN(CC)C(=O)N1C=NC(S(=O)(=O)C=2C(=CC(C)=CC=2C)C)=N1 HFEJHAAIJZXXRE-UHFFFAOYSA-N 0.000 claims description 3
- VJYIFXVZLXQVHO-UHFFFAOYSA-N chlorsulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 claims description 3
- YUIKUTLBPMDDNQ-MRVPVSSYSA-N clodinafop Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=NC=C(Cl)C=C1F YUIKUTLBPMDDNQ-MRVPVSSYSA-N 0.000 claims description 3
- YIANBKOBVRMNPR-UHFFFAOYSA-N cloransulam Chemical compound N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1C(O)=O YIANBKOBVRMNPR-UHFFFAOYSA-N 0.000 claims description 3
- MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical compound NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 claims description 3
- 229940097068 glyphosate Drugs 0.000 claims description 3
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 claims description 3
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 claims description 3
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 claims description 3
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 claims description 3
- JZPKLLLUDLHCEL-UHFFFAOYSA-N pentoxazone Chemical compound O=C1C(=C(C)C)OC(=O)N1C1=CC(OC2CCCC2)=C(Cl)C=C1F JZPKLLLUDLHCEL-UHFFFAOYSA-N 0.000 claims description 3
- CSWIKHNSBZVWNQ-UHFFFAOYSA-N pethoxamide Chemical compound CCOCCN(C(=O)CCl)C(=C(C)C)C1=CC=CC=C1 CSWIKHNSBZVWNQ-UHFFFAOYSA-N 0.000 claims description 3
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 claims description 3
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 claims description 3
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 claims description 3
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 claims description 3
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 claims description 3
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 claims description 3
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 claims description 3
- ROBSGBGTWRRYSK-SNVBAGLBSA-N (2r)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CC=C(C#N)C=C1F ROBSGBGTWRRYSK-SNVBAGLBSA-N 0.000 claims description 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- MZHCENGPTKEIGP-RXMQYKEDSA-N (R)-dichlorprop Chemical compound OC(=O)[C@@H](C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-RXMQYKEDSA-N 0.000 claims description 2
- MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- YUVKUEAFAVKILW-UHFFFAOYSA-N 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 YUVKUEAFAVKILW-UHFFFAOYSA-N 0.000 claims description 2
- HCNBYBFTNHEQQJ-UHFFFAOYSA-N 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-6-(trifluoromethyl)pyridine-3-carboxylic acid Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(N=2)C(F)(F)F)C(O)=O)=N1 HCNBYBFTNHEQQJ-UHFFFAOYSA-N 0.000 claims description 2
- KRQUFUKTQHISJB-YYADALCUSA-N 2-[(E)-N-[2-(4-chlorophenoxy)propoxy]-C-propylcarbonimidoyl]-3-hydroxy-5-(thian-3-yl)cyclohex-2-en-1-one Chemical compound CCC\C(=N/OCC(C)OC1=CC=C(Cl)C=C1)C1=C(O)CC(CC1=O)C1CCCSC1 KRQUFUKTQHISJB-YYADALCUSA-N 0.000 claims description 2
- OOLBCHYXZDXLDS-UHFFFAOYSA-N 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1Cl OOLBCHYXZDXLDS-UHFFFAOYSA-N 0.000 claims description 2
- CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 claims description 2
- YHKBGVDUSSWOAB-UHFFFAOYSA-N 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoic acid Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(CC(Cl)C(O)=O)=C(Cl)C=C1F YHKBGVDUSSWOAB-UHFFFAOYSA-N 0.000 claims description 2
- MBFHUWCOCCICOK-UHFFFAOYSA-N 4-iodo-2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoic acid Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(I)C=2)C(O)=O)=N1 MBFHUWCOCCICOK-UHFFFAOYSA-N 0.000 claims description 2
- NYRMIJKDBAQCHC-UHFFFAOYSA-N 5-(methylamino)-2-phenyl-4-[3-(trifluoromethyl)phenyl]furan-3(2H)-one Chemical compound O1C(NC)=C(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C1C1=CC=CC=C1 NYRMIJKDBAQCHC-UHFFFAOYSA-N 0.000 claims description 2
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- 230000014616 translation Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19836725A DE19836725A1 (de) | 1998-08-13 | 1998-08-13 | Herbizide Mittel mit acylierten Aminophenylsulfonylharnstoffen |
| DE1999119853 DE19919853A1 (de) | 1999-04-30 | 1999-04-30 | Herbizide Mittel mit acylierten Aminophenylsulfonylharnstoffen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ2001557A3 CZ2001557A3 (en) | 2001-06-13 |
| CZ303977B6 true CZ303977B6 (cs) | 2013-07-31 |
Family
ID=26048133
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ20010557A CZ303977B6 (cs) | 1998-08-13 | 1999-08-10 | Herbicidní prostredek s acylovanými aminofenylsulfonylmocovinami a zpusob hubení skodlivých rostlin |
Country Status (31)
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19520839A1 (de) * | 1995-06-08 | 1996-12-12 | Hoechst Schering Agrevo Gmbh | Herbizide Mittel mit 4-Iodo-2-[3- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) ureidosulfonyl] -benzoesäureestern |
| CN100518511C (zh) * | 1998-08-13 | 2009-07-29 | 拜尔作物科学股份公司 | 含有酰化氨基苯基磺酰脲类的除草用组合物 |
| DE19853827A1 (de) * | 1998-11-21 | 2000-05-25 | Aventis Cropscience Gmbh | Kombinationen aus Herbiziden und Safenern |
| US6689719B2 (en) | 1999-08-11 | 2004-02-10 | Monsanto Technology Llc | Coformulation of carfentrazone-ethyl and glyphasate |
| US6713433B2 (en) | 1999-08-11 | 2004-03-30 | Monsanto Technology, Llc | Coformulation of an oil-soluble herbicide and a water-soluble herbicide |
| CN1679396A (zh) * | 2000-04-04 | 2005-10-12 | 巴斯福股份公司 | 增效除草混合物 |
| US6967188B2 (en) * | 2000-05-22 | 2005-11-22 | Bayer Cropscience Ag | Selective heteroaryloxy- acetamides-based herbicides |
| SI1315420T1 (sl) * | 2000-08-31 | 2006-10-31 | Basf Ag | Herbicidne zmesi |
| BR0206799B1 (pt) * | 2001-01-31 | 2013-05-28 | combinaÇço de herbicida-protetor À base de protetores de carboxilato de isoxazolina e mÉtodos de combate Às ervas daninhas e para reduzir a fitotoxicidade de um herbicida. | |
| GB0114198D0 (en) * | 2001-06-11 | 2001-08-01 | Syngenta Ltd | Herbicidal composition |
| DE10135641A1 (de) * | 2001-07-21 | 2003-02-06 | Bayer Cropscience Gmbh | Herbizid-Kombinationen mit speziellen Sulfonylharnstoffen |
| AR036546A1 (es) * | 2001-09-20 | 2004-09-15 | Syngenta Participations Ag | Composicion herbicida |
| WO2003028450A2 (en) * | 2001-09-27 | 2003-04-10 | Syngenta Participations Ag | Herbicidal composition |
| DE10160139A1 (de) | 2001-12-07 | 2003-06-18 | Bayer Cropscience Gmbh | Synergistische herbizide Mittel enthaltend bestimmte Herbizide aus der Gruppe der Benzoylcylohexandione |
| TW200401610A (en) * | 2002-07-08 | 2004-02-01 | Basf Ag | Synergistically acting herbicidal mixtures |
| US7214825B2 (en) | 2003-10-17 | 2007-05-08 | Honeywell International Inc. | O-(3-chloropropenyl) hydroxylamine free base |
| JP2006257063A (ja) * | 2005-03-17 | 2006-09-28 | Maruwa Biochemical Co Ltd | 保存安定性を向上させた油性懸濁除草製剤。 |
| RU2288581C1 (ru) * | 2005-08-23 | 2006-12-10 | Закрытое акционерное общество Фирма "Август" | Синергетическая гербицидная композиция и способ борьбы с сорными растениями |
| JP5173172B2 (ja) * | 2005-09-28 | 2013-03-27 | 石原産業株式会社 | 除草組成物 |
| US8138122B2 (en) * | 2006-04-28 | 2012-03-20 | Sumitomo Chemical Company, Limited | Herbicidal composition |
| RU2351133C1 (ru) * | 2007-08-02 | 2009-04-10 | Закрытое акционерное общество Фирма "Август" | Гербицидная композиция и способ борьбы с сорными растениями в посевах кукурузы |
| US20110118120A1 (en) * | 2009-11-13 | 2011-05-19 | Dow Agrosciences Llc | Synergistic herbicidal composition containing aminopyralid and sulfonylureas |
| WO2011082956A2 (de) | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
| PT2515658T (pt) | 2009-12-17 | 2016-09-13 | Bayer Ip Gmbh | Composições herbicidas contendo flufenacet |
| EP2512249B1 (de) | 2009-12-17 | 2016-06-01 | Bayer Intellectual Property GmbH | Herbizide mittel enthaltend flufenacet |
| WO2011082959A2 (de) * | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
| WO2011082964A1 (de) | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
| WO2011082968A2 (de) * | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
| WO2011082953A2 (de) | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
| WO2011082955A2 (de) | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
| WO2011082957A2 (de) | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
| WO2011082954A2 (de) | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
| HUE030350T2 (en) | 2009-12-17 | 2017-05-29 | Bayer Ip Gmbh | Herbicidal preparations containing flufenacet |
| CN101953373A (zh) * | 2010-10-22 | 2011-01-26 | 吉林金秋农药有限公司 | 一种除草剂组合物及其制作方法和用途 |
| JP5875924B2 (ja) * | 2011-04-14 | 2016-03-02 | 石原産業株式会社 | 除草組成物 |
| PL2708124T3 (pl) * | 2011-11-10 | 2018-09-28 | Rotam Agrochem International Co., Ltd | Kompozycja chwastobójcza i sposób jej stosowania |
| IN2014DN07418A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2012-03-09 | 2015-04-24 | Ishihara Sangyo Kaisha | |
| WO2014001357A1 (de) | 2012-06-27 | 2014-01-03 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
| DK2866560T3 (en) | 2012-06-27 | 2019-04-01 | Bayer Cropscience Ag | HERBICIDE AGENTS CONTAINING FLUFENACET |
| WO2014001248A1 (de) | 2012-06-27 | 2014-01-03 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
| WO2014001361A1 (de) | 2012-06-27 | 2014-01-03 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
| CN103300039A (zh) * | 2013-07-12 | 2013-09-18 | 安徽丰乐农化有限责任公司 | 一种玉米苗后复配除草剂 |
| CN103392724B (zh) * | 2013-08-07 | 2015-07-15 | 广西壮族自治区农业科学院植物保护研究所 | 一种木薯田除草剂组合物用于防治香附子的用途 |
| US9072298B2 (en) * | 2013-11-01 | 2015-07-07 | Rotam Agrochem Intrnational Company Limited | Synergistic herbicidal composition |
| EP2936983A1 (de) | 2014-04-25 | 2015-10-28 | Bayer CropScience AG | Wirkstoffe zur Ertragssteigerung in Baumwollkulturen |
| UA119191C2 (uk) | 2014-12-15 | 2019-05-10 | Байєр Кропсайєнс Акцієнгезелльшафт | Кристалічні форми мононатрієвої солі форамсульфурону |
| CN104642366A (zh) * | 2015-02-16 | 2015-05-27 | 河北博嘉农业有限公司 | 一种增效除草组合物 |
| CN104686557A (zh) * | 2015-03-26 | 2015-06-10 | 河北博嘉农业有限公司 | 一种含有甲酰氨基嘧磺隆的增效除草组合物 |
| CN105360150B (zh) * | 2015-12-20 | 2018-04-17 | 安徽蓝田农业开发有限公司 | 一种含唑草胺除草剂组合物 |
| GB2545732B (en) * | 2015-12-23 | 2019-11-13 | Rotam Agrochem Int Co Ltd | Herbicidal composition and use thereof |
| CA3130265A1 (en) | 2019-02-19 | 2020-08-27 | Gowan Company, L.L.C. | Stable liquid compositions and methods of using the same |
| US11576381B2 (en) | 2019-02-25 | 2023-02-14 | Albaugh, Llc | Composition and a method of using the composition to increase wheat yield |
| CN114277080B (zh) * | 2021-12-22 | 2023-10-03 | 河北威远生物化工有限公司 | 一种酶拆分法制备l-草铵膦的工艺 |
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|---|---|---|---|---|
| WO1994010154A1 (de) * | 1992-10-31 | 1994-05-11 | Hoechst Schering Agrevo Gmbh | Neue phenylsulfonylharnstoffe, ihre darstellung und ihre verwendung als herbizide und pflanzenwachstumsregulatoren |
| DE19520839A1 (de) * | 1995-06-08 | 1996-12-12 | Hoechst Schering Agrevo Gmbh | Herbizide Mittel mit 4-Iodo-2-[3- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) ureidosulfonyl] -benzoesäureestern |
| WO1997010714A1 (de) * | 1995-09-20 | 1997-03-27 | Basf Aktiengesellschaft | Herbizide mischungen mit synergistischer wirkung |
| DE19642082A1 (de) * | 1996-10-04 | 1998-04-09 | Hoechst Schering Agrevo Gmbh | Herbizide Mittel mit synergistischer Wirkung |
| DE19650955A1 (de) * | 1996-12-07 | 1998-06-10 | Hoechst Schering Agrevo Gmbh | Herbizide Mittel mit N- [(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl] -5-methylsulfonamidomethyl-2-alkoxycarbonylbenzolsulfonamiden |
| EP1104239B1 (de) * | 1998-08-13 | 2004-02-18 | Bayer CropScience GmbH | Herbizide mittel mit acylierten aminophenylsulfonylharnstoffen |
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| DE4435373A1 (de) * | 1994-09-22 | 1996-03-28 | Hoechst Schering Agrevo Gmbh | Substituierte Pyrazolyl-pyrazolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Mittel mit herbizider Wirkung |
| DE4440354A1 (de) * | 1994-11-11 | 1996-05-15 | Hoechst Schering Agrevo Gmbh | Kombinationen aus Phenylsulfonylharnstoff-Herbiziden und Safenern |
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1999
- 1999-08-10 CN CNB998096148A patent/CN100518511C/zh not_active Expired - Lifetime
- 1999-08-10 ID IDW20010340A patent/ID28990A/id unknown
- 1999-08-10 JP JP2000564446A patent/JP4480890B2/ja not_active Expired - Lifetime
- 1999-08-10 ES ES99942833T patent/ES2216559T3/es not_active Expired - Lifetime
- 1999-08-10 PT PT99942833T patent/PT1104239E/pt unknown
- 1999-08-10 TR TR2001/00458T patent/TR200100458T2/xx unknown
- 1999-08-10 SK SK214-2001A patent/SK286487B6/sk not_active IP Right Cessation
- 1999-08-10 US US09/371,355 patent/US6486096B1/en not_active Expired - Lifetime
- 1999-08-10 KR KR20017001896A patent/KR100682203B1/ko not_active Expired - Lifetime
- 1999-08-10 RU RU2001107015/04A patent/RU2245621C2/ru active Protection Beyond IP Right Term
- 1999-08-10 BR BRPI9913641-4A patent/BRPI9913641B1/pt active IP Right Grant
- 1999-08-10 RS YUP-111/01A patent/RS49989B/sr unknown
- 1999-08-10 PL PL346048A patent/PL196990B1/pl unknown
- 1999-08-10 AU AU56207/99A patent/AU5620799A/en not_active Abandoned
- 1999-08-10 EP EP99942833A patent/EP1104239B1/de not_active Expired - Lifetime
- 1999-08-10 DE DE59908594T patent/DE59908594D1/de not_active Expired - Lifetime
- 1999-08-10 HU HU0103676A patent/HU228523B1/hu unknown
- 1999-08-10 WO PCT/EP1999/005800 patent/WO2000008932A1/de active IP Right Grant
- 1999-08-10 SI SI9930552T patent/SI1104239T1/xx unknown
- 1999-08-10 CA CA2340241A patent/CA2340241C/en not_active Expired - Lifetime
- 1999-08-10 CZ CZ20010557A patent/CZ303977B6/cs not_active IP Right Cessation
- 1999-08-10 AT AT99942833T patent/ATE259594T1/de active
- 1999-08-10 DK DK99942833T patent/DK1104239T3/da active
- 1999-08-10 HR HR20010104A patent/HRP20010104B1/xx not_active IP Right Cessation
- 1999-08-11 AR ARP990104019A patent/AR020164A1/es active IP Right Grant
- 1999-08-11 TW TW088113753A patent/TW584542B/zh not_active IP Right Cessation
- 1999-08-12 MY MYPI99003458A patent/MY124065A/en unknown
- 1999-08-12 PH PH11999002051A patent/PH11999002051B1/en unknown
- 1999-10-08 UA UA2001031683A patent/UA71568C2/uk unknown
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2001
- 2001-02-08 IN IN188CH2001 patent/IN2001CH00188A/en unknown
- 2001-02-13 MX MXPA01001645 patent/MXPA01001645A/es unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994010154A1 (de) * | 1992-10-31 | 1994-05-11 | Hoechst Schering Agrevo Gmbh | Neue phenylsulfonylharnstoffe, ihre darstellung und ihre verwendung als herbizide und pflanzenwachstumsregulatoren |
| DE19520839A1 (de) * | 1995-06-08 | 1996-12-12 | Hoechst Schering Agrevo Gmbh | Herbizide Mittel mit 4-Iodo-2-[3- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) ureidosulfonyl] -benzoesäureestern |
| WO1997010714A1 (de) * | 1995-09-20 | 1997-03-27 | Basf Aktiengesellschaft | Herbizide mischungen mit synergistischer wirkung |
| DE19642082A1 (de) * | 1996-10-04 | 1998-04-09 | Hoechst Schering Agrevo Gmbh | Herbizide Mittel mit synergistischer Wirkung |
| DE19650955A1 (de) * | 1996-12-07 | 1998-06-10 | Hoechst Schering Agrevo Gmbh | Herbizide Mittel mit N- [(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl] -5-methylsulfonamidomethyl-2-alkoxycarbonylbenzolsulfonamiden |
| EP1104239B1 (de) * | 1998-08-13 | 2004-02-18 | Bayer CropScience GmbH | Herbizide mittel mit acylierten aminophenylsulfonylharnstoffen |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Patent expired |
Effective date: 20190810 |