BRPI0111008B1 - agentes herbicidas seletivos à base de heteroarilóxi acetamidas, seu emprego e seu processo de preparação, bem como processo para o combate de plantas indesejadas - Google Patents
agentes herbicidas seletivos à base de heteroarilóxi acetamidas, seu emprego e seu processo de preparação, bem como processo para o combate de plantas indesejadas Download PDFInfo
- Publication number
- BRPI0111008B1 BRPI0111008B1 BRPI0111008A BR0111008A BRPI0111008B1 BR PI0111008 B1 BRPI0111008 B1 BR PI0111008B1 BR PI0111008 A BRPI0111008 A BR PI0111008A BR 0111008 A BR0111008 A BR 0111008A BR PI0111008 B1 BRPI0111008 B1 BR PI0111008B1
- Authority
- BR
- Brazil
- Prior art keywords
- methyl
- ethyl
- phenyl
- chloro
- sodium
- Prior art date
Links
- -1 heteroaryl acetamide Chemical compound 0.000 title claims abstract description 42
- 239000004009 herbicide Substances 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 title claims description 11
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 title abstract description 7
- 238000002360 preparation method Methods 0.000 title description 4
- 239000013543 active substance Substances 0.000 claims abstract description 67
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 239000005531 Flufenacet Substances 0.000 claims description 35
- 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 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 150000004702 methyl esters Chemical class 0.000 claims description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- NNKKTZOEKDFTBU-YBEGLDIGSA-N cinidon ethyl Chemical compound C1=C(Cl)C(/C=C(\Cl)C(=O)OCC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1 NNKKTZOEKDFTBU-YBEGLDIGSA-N 0.000 claims description 6
- JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;n-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical compound [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 claims description 6
- 239000005529 Florasulam Substances 0.000 claims description 5
- 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 5
- SMDHCQAYESWHAE-UHFFFAOYSA-N benfluralin Chemical compound CCCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O SMDHCQAYESWHAE-UHFFFAOYSA-N 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 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 4
- 239000005471 Benfluralin Substances 0.000 claims description 3
- UOUXAYAIONPXDH-UHFFFAOYSA-M flucarbazone-sodium Chemical compound [Na+].O=C1N(C)C(OC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1OC(F)(F)F UOUXAYAIONPXDH-UHFFFAOYSA-M 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- KKCLIBMLUMCTMZ-UHFFFAOYSA-N 3-methoxy-4-methyl-5-oxo-n-[2-(trifluoromethoxy)phenyl]sulfonyl-1,2,4-triazole-1-carboxamide;sodium Chemical compound [Na].O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1OC(F)(F)F KKCLIBMLUMCTMZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- 239000005578 Mesotrione Substances 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000004604 Blowing Agent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 abstract description 36
- 230000002363 herbicidal effect Effects 0.000 abstract description 15
- 244000038559 crop plants Species 0.000 abstract description 13
- 230000002195 synergetic effect Effects 0.000 abstract description 9
- 239000000203 mixture Substances 0.000 description 13
- 238000009472 formulation Methods 0.000 description 10
- 239000000460 chlorine Chemical group 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 239000011737 fluorine Substances 0.000 description 8
- 125000001153 fluoro group Chemical group F* 0.000 description 8
- YNQSILKYZQZHFJ-UHFFFAOYSA-N R-29148 Chemical compound CC1CN(C(=O)C(Cl)Cl)C(C)(C)O1 YNQSILKYZQZHFJ-UHFFFAOYSA-N 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 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 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- QWWHRELOCZEQNZ-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC11CCCCC1 QWWHRELOCZEQNZ-UHFFFAOYSA-N 0.000 description 5
- 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 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- CAQWNKXTMBFBGI-UHFFFAOYSA-N C.[Na] Chemical compound C.[Na] CAQWNKXTMBFBGI-UHFFFAOYSA-N 0.000 description 5
- 239000005566 Imazamox Substances 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical compound C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 5
- 241000894007 species Species 0.000 description 5
- FOMHMPJALXOZGZ-UHFFFAOYSA-N 2,2-dichloro-1-(2,2-dimethyl-1,3-oxazolidin-3-yl)ethanone Chemical compound CC1(C)OCCN1C(=O)C(Cl)Cl FOMHMPJALXOZGZ-UHFFFAOYSA-N 0.000 description 4
- MCNOFYBITGAAGM-UHFFFAOYSA-N 2,2-dichloro-1-[5-(furan-2-yl)-2,2-dimethyl-1,3-oxazolidin-3-yl]ethanone Chemical compound C1N(C(=O)C(Cl)Cl)C(C)(C)OC1C1=CC=CO1 MCNOFYBITGAAGM-UHFFFAOYSA-N 0.000 description 4
- QNXAVFXEJCPCJO-UHFFFAOYSA-N Diclosulam Chemical compound N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1Cl QNXAVFXEJCPCJO-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JUJFQMPKBJPSFZ-UHFFFAOYSA-M Iodosulfuron-methyl-sodium Chemical compound [Na+].COC(=O)C1=CC=C(I)C=C1S(=O)(=O)[N-]C(=O)NC1=NC(C)=NC(OC)=N1 JUJFQMPKBJPSFZ-UHFFFAOYSA-M 0.000 description 4
- 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 description 4
- PQKBPHSEKWERTG-LLVKDONJSA-N ethyl (2r)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoate Chemical compound C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-LLVKDONJSA-N 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000011734 sodium Chemical class 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 3
- MHULQDZDXMHODA-UHFFFAOYSA-N 1-(2,2-dichloroacetyl)-3,3,8a-trimethyl-2,4,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-6-one Chemical compound C1C(C)(C)CN(C(=O)C(Cl)Cl)C2(C)N1C(=O)CC2 MHULQDZDXMHODA-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 3
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000209219 Hordeum Species 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000209094 Oryza Species 0.000 description 3
- CNILNQMBAHKMFS-UHFFFAOYSA-M Pyrithiobac-sodium Chemical compound [Na+].COC1=CC(OC)=NC(SC=2C(=C(Cl)C=CC=2)C([O-])=O)=N1 CNILNQMBAHKMFS-UHFFFAOYSA-M 0.000 description 3
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- XOEMATDHVZOBSG-UHFFFAOYSA-N azafenidin Chemical compound C1=C(OCC#C)C(Cl)=CC(Cl)=C1N1C(=O)N2CCCCC2=N1 XOEMATDHVZOBSG-UHFFFAOYSA-N 0.000 description 3
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- FOUWCSDKDDHKQP-UHFFFAOYSA-N flumioxazin Chemical compound FC1=CC=2OCC(=O)N(CC#C)C=2C=C1N(C1=O)C(=O)C2=C1CCCC2 FOUWCSDKDDHKQP-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
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- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- JSYGRUBHOCKMGQ-UHFFFAOYSA-N dichloramine Chemical compound ClNCl JSYGRUBHOCKMGQ-UHFFFAOYSA-N 0.000 description 1
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- 150000002191 fatty alcohols Chemical class 0.000 description 1
- DNUAYCRATWAJQE-UHFFFAOYSA-N flufenpyr-ethyl Chemical compound C1=C(Cl)C(OCC(=O)OCC)=CC(N2C(C(C)=C(C=N2)C(F)(F)F)=O)=C1F DNUAYCRATWAJQE-UHFFFAOYSA-N 0.000 description 1
- PXDNXJSDGQBLKS-UHFFFAOYSA-N foramsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(NC=O)C=2)C(=O)N(C)C)=N1 PXDNXJSDGQBLKS-UHFFFAOYSA-N 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
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- 235000021021 grapes Nutrition 0.000 description 1
- MFSWTRQUCLNFOM-SECBINFHSA-N haloxyfop-P-methyl Chemical group C1=CC(O[C@H](C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-SECBINFHSA-N 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
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- 229920000126 latex Polymers 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- JCHMGYRXQDASJE-UHFFFAOYSA-N metcamifen Chemical compound C1=CC(NC(=O)NC)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1OC JCHMGYRXQDASJE-UHFFFAOYSA-N 0.000 description 1
- VSKPNJHIWOZOCQ-UHFFFAOYSA-N methyl 2-(4,6-dimethoxypyrimidin-2-yl)oxybenzoate Chemical compound COC(=O)C1=CC=CC=C1OC1=NC(OC)=CC(OC)=N1 VSKPNJHIWOZOCQ-UHFFFAOYSA-N 0.000 description 1
- XVPAYLVQXRJFBG-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-6-(trifluoromethyl)pyridine-3-carboxylate;sodium Chemical compound [Na].COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XVPAYLVQXRJFBG-UHFFFAOYSA-N 0.000 description 1
- LYPWWQLKWQNQKV-UHFFFAOYSA-N methyl 2-[5-ethyl-2-[[4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]methyl]phenoxy]propanoate Chemical compound COC(=O)C(C)OC1=CC(CC)=CC=C1COC1=CC=C(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)C=C1 LYPWWQLKWQNQKV-UHFFFAOYSA-N 0.000 description 1
- BEPNBXQVLQBNNS-UHFFFAOYSA-N methyl 4-iodo-2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoate;sodium Chemical compound [Na].COC(=O)C1=CC=C(I)C=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 BEPNBXQVLQBNNS-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
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- 229910052750 molybdenum Inorganic materials 0.000 description 1
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- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- CSWIKHNSBZVWNQ-UHFFFAOYSA-N pethoxamide Chemical compound CCOCCN(C(=O)CCl)C(=C(C)C)C1=CC=CC=C1 CSWIKHNSBZVWNQ-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
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- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 230000001737 promoting effect Effects 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
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- 150000003254 radicals Chemical class 0.000 description 1
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- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
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- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—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
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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10025306 | 2000-05-22 | ||
| DE10041619A DE10041619A1 (de) | 2000-05-22 | 2000-08-24 | Selektive Herbizide auf Basis von Heteroaryloxyacetamiden |
| PCT/EP2001/005242 WO2001089301A1 (de) | 2000-05-22 | 2001-05-09 | Selektive herbizide auf basis von heteroaryloxy-acetamiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR0111008A BR0111008A (pt) | 2003-04-08 |
| BRPI0111008B1 true BRPI0111008B1 (pt) | 2015-12-15 |
Family
ID=26005781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0111008A BRPI0111008B1 (pt) | 2000-05-22 | 2001-05-09 | agentes herbicidas seletivos à base de heteroarilóxi acetamidas, seu emprego e seu processo de preparação, bem como processo para o combate de plantas indesejadas |
Country Status (15)
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|---|---|
| US (2) | US6967188B2 (enExample) |
| EP (1) | EP1298996A1 (enExample) |
| JP (1) | JP2003533545A (enExample) |
| KR (1) | KR100781758B1 (enExample) |
| CN (1) | CN1430471A (enExample) |
| AU (2) | AU2001265936B2 (enExample) |
| BR (1) | BRPI0111008B1 (enExample) |
| CA (1) | CA2409215A1 (enExample) |
| CZ (1) | CZ301614B6 (enExample) |
| HR (1) | HRP20021022A2 (enExample) |
| HU (1) | HU230428B1 (enExample) |
| MX (1) | MXPA02011468A (enExample) |
| PL (1) | PL218432B1 (enExample) |
| SK (1) | SK287461B6 (enExample) |
| WO (1) | WO2001089301A1 (enExample) |
Families Citing this family (41)
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| US6962894B1 (en) * | 1999-09-07 | 2005-11-08 | Syngenta Crop Protection, Inc. | Herbicidal composition |
| GB0022833D0 (en) | 2000-09-18 | 2000-11-01 | Aventis Cropscience Sa | New herbicidal composition |
| AR036047A1 (es) * | 2001-06-13 | 2004-08-04 | Syngenta Participations Ag | Composicion herbicida selectiva y metodo para controlar selectivamente malezas y pastos en cultivos de plantas utiles |
| DE10135642A1 (de) | 2001-07-21 | 2003-02-27 | Bayer Cropscience Gmbh | Herbizid-Kombinationen mit speziellen Sulfonylharnstoffen |
| DE10209478A1 (de) * | 2002-03-05 | 2003-09-18 | Bayer Cropscience Gmbh | Herbizid-Kombinationen mit speziellen Sulfonylharnstoffen |
| EP1484974A1 (en) * | 2002-03-21 | 2004-12-15 | Syngenta Participations AG | Herbicidal composition |
| MY141982A (en) * | 2004-12-21 | 2010-08-16 | Syngenta Participations Ag | Herbicidal composition |
| US20100285959A1 (en) * | 2006-04-10 | 2010-11-11 | Gregory Russell Armel | Herbicidal mixtures |
| EP1974609A1 (de) * | 2007-03-29 | 2008-10-01 | Bayer CropScience GmbH | Verfahren zur Herstellung von wasserdispergierbaren Granulaten (WG) |
| AR069022A1 (es) * | 2007-10-26 | 2009-12-23 | Kumiai Chemical Industry Co | Agente para incrementar el contenido de azucar de la caña de azucar asi como metodo para acelerar la maduracion de la caña de azucar utilizando el mismo |
| EP2057898A1 (de) * | 2007-11-06 | 2009-05-13 | Bayer CropScience AG | Homogene und lagerstabile Mischungen unterschiedlicher Pflanzenchutzmittel-Wirkstoff-Granulatpartikel |
| US20090215625A1 (en) * | 2008-01-07 | 2009-08-27 | Auburn University | Combinations of Herbicides and Safeners |
| RU2010134763A (ru) * | 2008-02-12 | 2012-03-20 | Ариста Лайфсайенс Норс Америка, Ллс (Us) | Способ контроля нежелательной вегетации |
| JP5563773B2 (ja) * | 2008-12-17 | 2014-07-30 | バイエル・クロップサイエンス・アーゲー | 除草剤組成物 |
| DE102008062905A1 (de) * | 2008-12-23 | 2010-06-24 | Saltigo Gmbh | Verfahren zur Herstellung von Acylamid-Verbindungen |
| WO2011082954A2 (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 |
| WO2011082957A2 (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 |
| DK2515658T3 (en) * | 2009-12-17 | 2016-09-12 | Bayer Ip Gmbh | HERBICIDE AGENTS CONTAINING FLUFENACET |
| EP2512248B1 (de) * | 2009-12-17 | 2016-08-10 | Bayer Intellectual Property GmbH | Herbizide mittel enthaltend flufenacet |
| WO2011082956A2 (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 |
| WO2011082959A2 (de) * | 2009-12-17 | 2011-07-14 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
| ES2589047T3 (es) | 2009-12-17 | 2016-11-08 | Bayer Intellectual Property Gmbh | Agentes herbicidas que contienen flufenacet |
| CN102239854A (zh) * | 2011-05-18 | 2011-11-16 | 利尔化学股份有限公司 | 除草农药组合物 |
| HRP20190490T1 (hr) | 2012-06-27 | 2019-05-03 | Bayer Cropscience Ag | Herbicidna sredstva koja sadrže flufenacet |
| WO2014001357A1 (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 |
| WO2014001248A1 (de) | 2012-06-27 | 2014-01-03 | Bayer Cropscience Ag | Herbizide mittel enthaltend flufenacet |
| EA026809B1 (ru) | 2012-12-21 | 2017-05-31 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Термостабильные водные композиции клоквинтосет-мексила |
| US9717244B2 (en) | 2013-02-25 | 2017-08-01 | Dow Agrosciences Llc | Methods of weed control in pineapple |
| CA2902437A1 (en) | 2013-03-15 | 2014-09-25 | Dow Agrosciences Llc | Synergistic weed control from applications of penoxsulam and pethoxamid |
| EP2936983A1 (de) | 2014-04-25 | 2015-10-28 | Bayer CropScience AG | Wirkstoffe zur Ertragssteigerung in Baumwollkulturen |
| CN104365628A (zh) * | 2014-11-06 | 2015-02-25 | 江苏省农用激素工程技术研究中心有限公司 | 用于防治大豆田杂草的除草组合物 |
| GB2532217B (en) * | 2014-11-11 | 2019-05-15 | Rotam Agrochem Int Co Ltd | Herbicidal composition and method for controlling plant growth |
| CN105454266A (zh) * | 2015-12-23 | 2016-04-06 | 汤云鹤 | 一种含氟噻草胺、异丙隆和双氟磺草胺的农药组合物及其在防治小麦田杂草中的应用 |
| CN106689141A (zh) * | 2017-03-10 | 2017-05-24 | 合肥星宇化学有限责任公司 | 丙酯草醚和喹禾糠酯复配除草组合物及其制剂和应用 |
| CN107751226B (zh) * | 2017-11-27 | 2020-11-13 | 浙江永太药业有限公司 | 一种含哒草特和氟噻草胺的除草剂组合物 |
| CN114208833B (zh) * | 2021-12-30 | 2024-03-29 | 青岛润农化工有限公司 | 含氟草烟异辛酯和双氯磺草胺的农药组合物及其制备方法和应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0005501B1 (de) | 1978-05-20 | 1981-11-25 | Bayer Ag | Heteroaryl-oxyessigsäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide |
| DE3060330D1 (en) | 1979-04-06 | 1982-06-09 | Bayer Ag | Azolyloxy-acetamides, process for their preparation and their use as herbicides |
| DE2946524A1 (de) | 1979-11-17 | 1981-06-11 | Bayer Ag, 5090 Leverkusen | Azolyloxy-carbonsaeure-n-oxy-amide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE3218482A1 (de) | 1982-05-15 | 1983-11-17 | Bayer Ag, 5090 Leverkusen | Substituierte 5-trifluormethyl-1,3,4-thiadiazol-2-yloxyessigsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE3228147A1 (de) | 1982-07-28 | 1984-02-09 | Bayer Ag, 5090 Leverkusen | Substituierte 3-trihalogenmethyl-1,2,4-thiadiazol-5-yl-oxyessigsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE3228131A1 (de) | 1982-07-28 | 1984-02-02 | Bayer Ag, 5090 Leverkusen | Substituierte 3-trichlormethyl-1,2,4-thiadiazol-5-yl-oxyessigsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE3418168A1 (de) | 1984-05-16 | 1985-11-21 | Bayer Ag, 5090 Leverkusen | 6-chlorbenzazolyloxyacetamide |
| DE3418167A1 (de) | 1984-05-16 | 1985-11-21 | Bayer Ag, 5090 Leverkusen | Verwendung von amiden zur verbesserung der kulturpflanzen-vertraeglichkeit von herbizid wirksamen heteroaryloxyacetamiden |
| US4585899A (en) * | 1985-01-22 | 1986-04-29 | Chem Systems Inc. | Hydrogenation of carboxylic acid compounds to aldehydes using MnO2 on gamma alumina as catalyst |
| DE3505902A1 (de) | 1985-02-21 | 1986-08-21 | Bayer Ag, 5090 Leverkusen | 4,5-disubstituierte 1,3-thiazol-2-yloxyacetamide |
| DE3811446A1 (de) * | 1988-04-06 | 1989-10-19 | Bodenseewerk Perkin Elmer Co | Einrichtung zur erzeugung eines magnetfeldes in einem atomabsorptions-spektrometer |
| DE3821597A1 (de) | 1988-06-27 | 1989-12-28 | Bayer Ag | 5-difluormethyl-1,3,4-thiadiazol-2-yl- oxyessigsaeureamide, verfahren und 5-difluormethyl-2- methylsulfonyl- bzw. 2- methylthio-1,3,4-thiadiazol als zwischenprodukte zu ihrer herstellung und ihre verwendung als selektivherbizide |
| DE3821600A1 (de) | 1988-06-27 | 1989-12-28 | Bayer Ag | Heteroaryloxyessigsaeure-n-isopropylanilide |
| US5529976A (en) | 1990-01-10 | 1996-06-25 | Hoechst Aktiengesellschaft | Pyridyl sulphonyl ureas as herbicides and plant growth regulators |
| DE4223465A1 (de) * | 1992-07-16 | 1994-01-20 | Bayer Ag | Herbizide Mittel auf Basis von Heteroaryloxyacetamiden |
| DE4431219A1 (de) | 1994-09-02 | 1996-03-07 | Bayer Ag | Selektive Herbizide auf Basis von Aryluracilen |
| DE4437049A1 (de) * | 1994-10-17 | 1996-04-18 | Bayer Ag | Selektive Herbizide auf Basis von Carbamoyltriazolinonen und Heteroaryloxyacetamiden |
| US5912206A (en) | 1994-12-09 | 1999-06-15 | Rhone-Poulenc Agrochimie | Herbicidal compositions |
| DE19546751B4 (de) * | 1994-12-23 | 2005-02-17 | Bayer Cropscience Ag | Selektive Herbizide auf Basis von Heteroaryloxy-acetamiden |
| ES2128984B1 (es) * | 1996-05-24 | 2000-02-01 | Bayer Ag | Herbicidas a base de heteroariloxi-acetamidas para el empleo en el cultivo de arroz. |
| US5985797A (en) | 1996-07-17 | 1999-11-16 | Bayer Aktiengesellschaft | Herbicidal compositions based on N-isopropyl-N-(4-fluorophenyl) (5-trifluoromethyl-1,3,4-thiadiazol-2-yloxy)acetamide |
| DE19728568B4 (de) * | 1996-07-17 | 2007-06-14 | Bayer Cropscience Ag | Herbizide Mittel auf Basis von (5-Trifluormethyl-1,3,4-thiadiazol-2-yl-oxy)-essigsäure-N-isopropyl-N-(4fluorphenyl)-amid |
| DE19634701A1 (de) | 1996-08-28 | 1998-03-05 | Bayer Ag | Herbizide Mittel auf Basis von 4-Brom-l-methyl-5-trifluormethyl-3-(2-fluor-4-chlor-5-isopropoxycarbonsylphenyl)pyrazol |
| JPH10306007A (ja) * | 1997-05-06 | 1998-11-17 | Sumitomo Chem Co Ltd | 除草剤組成物 |
| AR012651A1 (es) * | 1997-05-06 | 2000-11-08 | Sumitomo Chemical Co | COMPOSICIoN HERBICIDA Y METODO DE DESMALEZADO UTILIZANDO LA MISMA. |
| TR200100101T2 (tr) * | 1998-07-16 | 2001-06-21 | Aventis Cropscience Gmbh | Herbisit ilaçlar. |
| DE19832017A1 (de) | 1998-07-16 | 2000-01-27 | Hoechst Schering Agrevo Gmbh | Herbizide Mittel mit substituierten Phenylsulfonylharnstoffen zur Unkrautbekämpfung in Reis |
| CA2340241C (en) * | 1998-08-13 | 2011-10-04 | Aventis Cropscience Gmbh | Herbicidal compositions with acylated aminophenylsulfonylureas |
| JP4200559B2 (ja) * | 1998-10-23 | 2008-12-24 | 住友化学株式会社 | 除草剤組成物 |
-
2001
- 2001-05-09 CA CA002409215A patent/CA2409215A1/en not_active Abandoned
- 2001-05-09 CZ CZ20023822A patent/CZ301614B6/cs not_active IP Right Cessation
- 2001-05-09 WO PCT/EP2001/005242 patent/WO2001089301A1/de not_active Ceased
- 2001-05-09 BR BRPI0111008A patent/BRPI0111008B1/pt active IP Right Grant
- 2001-05-09 KR KR1020027014810A patent/KR100781758B1/ko not_active Expired - Lifetime
- 2001-05-09 CN CN01809989A patent/CN1430471A/zh active Pending
- 2001-05-09 HU HU0302069A patent/HU230428B1/hu unknown
- 2001-05-09 JP JP2001585555A patent/JP2003533545A/ja active Pending
- 2001-05-09 HR HR20021022A patent/HRP20021022A2/xx not_active Application Discontinuation
- 2001-05-09 PL PL359033A patent/PL218432B1/pl not_active IP Right Cessation
- 2001-05-09 AU AU2001265936A patent/AU2001265936B2/en not_active Expired
- 2001-05-09 US US10/296,006 patent/US6967188B2/en not_active Expired - Lifetime
- 2001-05-09 AU AU6593601A patent/AU6593601A/xx active Pending
- 2001-05-09 EP EP01943335A patent/EP1298996A1/de not_active Withdrawn
- 2001-05-09 SK SK1626-2002A patent/SK287461B6/sk not_active IP Right Cessation
- 2001-05-09 MX MXPA02011468A patent/MXPA02011468A/es active IP Right Grant
-
2005
- 2005-08-10 US US11/200,639 patent/US20060009359A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US6967188B2 (en) | 2005-11-22 |
| SK16262002A3 (sk) | 2003-09-11 |
| HUP0302069A3 (en) | 2005-11-28 |
| HUP0302069A2 (hu) | 2003-09-29 |
| US20040102321A1 (en) | 2004-05-27 |
| PL218432B1 (pl) | 2014-12-31 |
| AU2001265936B2 (en) | 2006-04-06 |
| CN1430471A (zh) | 2003-07-16 |
| KR100781758B1 (ko) | 2007-12-04 |
| JP2003533545A (ja) | 2003-11-11 |
| AU6593601A (en) | 2001-12-03 |
| SK287461B6 (sk) | 2010-10-07 |
| CA2409215A1 (en) | 2002-11-19 |
| US20060009359A1 (en) | 2006-01-12 |
| CZ301614B6 (cs) | 2010-05-05 |
| HRP20021022A2 (en) | 2005-02-28 |
| PL359033A1 (en) | 2004-08-23 |
| EP1298996A1 (de) | 2003-04-09 |
| BR0111008A (pt) | 2003-04-08 |
| CZ20023822A3 (cs) | 2003-04-16 |
| KR20030027890A (ko) | 2003-04-07 |
| WO2001089301A1 (de) | 2001-11-29 |
| HU230428B1 (hu) | 2016-06-28 |
| MXPA02011468A (es) | 2004-08-12 |
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