BR0313241B1 - composição herbicida - Google Patents
composição herbicidaInfo
- Publication number
- BR0313241B1 BR0313241B1 BRPI0313241A BR0313241A BR0313241B1 BR 0313241 B1 BR0313241 B1 BR 0313241B1 BR PI0313241 A BRPI0313241 A BR PI0313241A BR 0313241 A BR0313241 A BR 0313241A BR 0313241 B1 BR0313241 B1 BR 0313241B1
- Authority
- BR
- Brazil
- Prior art keywords
- group
- groups
- optionally substituted
- alkyl
- component
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 200
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 82
- 150000001875 compounds Chemical class 0.000 claims abstract description 101
- 150000002547 isoxazolines Chemical class 0.000 claims abstract description 17
- -1 triphenylsulfuron Chemical compound 0.000 claims description 122
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 claims description 88
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 11
- 239000005562 Glyphosate Substances 0.000 claims description 9
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 claims description 7
- RXCPQSJAVKGONC-UHFFFAOYSA-N Flumetsulam Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(F)C=CC=C1F RXCPQSJAVKGONC-UHFFFAOYSA-N 0.000 claims description 7
- 239000005573 Linuron Substances 0.000 claims description 7
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 7
- 229940097068 glyphosate Drugs 0.000 claims description 7
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 6
- 239000003905 agrochemical Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000005578 Mesotrione Substances 0.000 claims description 4
- 239000005591 Pendimethalin Substances 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
- 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
- 239000005507 Diflufenican Substances 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 230000002195 synergetic effect Effects 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 abstract description 20
- 239000000243 solution Substances 0.000 description 329
- 238000006243 chemical reaction Methods 0.000 description 216
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 202
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 180
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 178
- 239000002904 solvent Substances 0.000 description 161
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 122
- 239000000460 chlorine Substances 0.000 description 116
- 238000005292 vacuum distillation Methods 0.000 description 115
- 238000004519 manufacturing process Methods 0.000 description 110
- 239000011541 reaction mixture Substances 0.000 description 105
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 104
- 239000012044 organic layer Substances 0.000 description 101
- 239000011780 sodium chloride Substances 0.000 description 101
- 238000000605 extraction Methods 0.000 description 95
- 238000005160 1H NMR spectroscopy Methods 0.000 description 79
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 77
- 239000007864 aqueous solution Substances 0.000 description 68
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 54
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 53
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 238000002360 preparation method Methods 0.000 description 50
- 125000000217 alkyl group Chemical group 0.000 description 49
- 238000010898 silica gel chromatography Methods 0.000 description 49
- 238000002844 melting Methods 0.000 description 48
- 230000008018 melting Effects 0.000 description 48
- 238000001816 cooling Methods 0.000 description 47
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 41
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 40
- 238000011161 development Methods 0.000 description 35
- 230000018109 developmental process Effects 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 32
- 239000013078 crystal Substances 0.000 description 31
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 31
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 30
- 125000001424 substituent group Chemical group 0.000 description 30
- 125000000753 cycloalkyl group Chemical group 0.000 description 29
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 28
- 229910052757 nitrogen Inorganic materials 0.000 description 28
- 125000003545 alkoxy group Chemical group 0.000 description 27
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 27
- 235000017557 sodium bicarbonate Nutrition 0.000 description 27
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 27
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 26
- 239000000843 powder Substances 0.000 description 25
- 125000002252 acyl group Chemical group 0.000 description 24
- 229910052739 hydrogen Inorganic materials 0.000 description 24
- 239000000126 substance Substances 0.000 description 23
- 241000196324 Embryophyta Species 0.000 description 22
- 125000001188 haloalkyl group Chemical group 0.000 description 22
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 description 22
- 239000012046 mixed solvent Substances 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 21
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 21
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 21
- 125000005843 halogen group Chemical group 0.000 description 20
- 150000002829 nitrogen Chemical class 0.000 description 20
- 229910000027 potassium carbonate Inorganic materials 0.000 description 20
- 235000011181 potassium carbonates Nutrition 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 16
- 231100000674 Phytotoxicity Toxicity 0.000 description 15
- 240000008042 Zea mays Species 0.000 description 15
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 15
- 125000004414 alkyl thio group Chemical group 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 14
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 235000005822 corn Nutrition 0.000 description 13
- 240000006995 Abutilon theophrasti Species 0.000 description 11
- 244000025254 Cannabis sativa Species 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 11
- 125000004438 haloalkoxy group Chemical group 0.000 description 11
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 11
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 239000004009 herbicide Substances 0.000 description 10
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 10
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 240000006122 Chenopodium album Species 0.000 description 9
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 9
- 125000000304 alkynyl group Chemical group 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 235000002248 Setaria viridis Nutrition 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 235000009344 Chenopodium album Nutrition 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- ZNKXTIAQRUWLRL-UHFFFAOYSA-M sodium;sulfane;hydroxide Chemical compound O.[Na+].[SH-] ZNKXTIAQRUWLRL-UHFFFAOYSA-M 0.000 description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- INCOVWJZVJYEAC-UHFFFAOYSA-N 5,5-dimethyl-3-methylsulfonyl-4h-1,2-oxazole Chemical compound CC1(C)CC(S(C)(=O)=O)=NO1 INCOVWJZVJYEAC-UHFFFAOYSA-N 0.000 description 6
- 235000003403 Limnocharis flava Nutrition 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 240000007594 Oryza sativa Species 0.000 description 6
- 235000007164 Oryza sativa Nutrition 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 240000002439 Sorghum halepense Species 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- 235000009566 rice Nutrition 0.000 description 6
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 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 description 5
- YMCWJQIZJIKFHO-UHFFFAOYSA-N 3-chloro-5,5-dimethyl-4h-1,2-oxazole Chemical compound CC1(C)CC(Cl)=NO1 YMCWJQIZJIKFHO-UHFFFAOYSA-N 0.000 description 5
- UTTVVZLFAXQNEP-UHFFFAOYSA-N 4-methoxy-6-(trifluoromethyl)pyrimidine-5-carbaldehyde Chemical compound COC1=NC=NC(C(F)(F)F)=C1C=O UTTVVZLFAXQNEP-UHFFFAOYSA-N 0.000 description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 239000005561 Glufosinate Substances 0.000 description 5
- 235000010469 Glycine max Nutrition 0.000 description 5
- 240000003461 Setaria viridis Species 0.000 description 5
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 5
- 244000062793 Sorghum vulgare Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 5
- 125000003226 pyrazolyl group Chemical group 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 5
- 125000004434 sulfur atom Chemical group 0.000 description 5
- UYGXIUVQGMFJNI-UHFFFAOYSA-N 2-tert-butyl-5-(trifluoromethyl)-1h-pyrazol-3-one Chemical compound CC(C)(C)N1NC(C(F)(F)F)=CC1=O UYGXIUVQGMFJNI-UHFFFAOYSA-N 0.000 description 4
- SAZSJTDSJGQWSZ-UHFFFAOYSA-N 3-[[3-chloro-1-(difluoromethyl)-5-(trifluoromethyl)pyrazol-4-yl]methylsulfanyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound O1C(C)(C)CC(SCC2=C(N(C(F)F)N=C2Cl)C(F)(F)F)=N1 SAZSJTDSJGQWSZ-UHFFFAOYSA-N 0.000 description 4
- SGTXWXKKONGNQJ-UHFFFAOYSA-N 3-[[5-chloro-1-(difluoromethyl)-3-(trifluoromethyl)pyrazol-4-yl]methylsulfanyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound O1C(C)(C)CC(SCC=2C(=NN(C=2Cl)C(F)F)C(F)(F)F)=N1 SGTXWXKKONGNQJ-UHFFFAOYSA-N 0.000 description 4
- ZFGOKCZHPVPBKY-UHFFFAOYSA-N 3-[[5-fluoro-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfanyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CN1N=C(C(F)(F)F)C(CSC=2CC(C)(C)ON=2)=C1F ZFGOKCZHPVPBKY-UHFFFAOYSA-N 0.000 description 4
- KHYCFJGUSXBDJZ-UHFFFAOYSA-N 4-(bromomethyl)-1-tert-butyl-5-chloro-3-(trifluoromethyl)pyrazole Chemical compound CC(C)(C)N1N=C(C(F)(F)F)C(CBr)=C1Cl KHYCFJGUSXBDJZ-UHFFFAOYSA-N 0.000 description 4
- JFRNHGWPQJPTCO-UHFFFAOYSA-N 5-bromo-4-chloro-6-(trifluoromethyl)pyrimidine Chemical compound FC(F)(F)C1=NC=NC(Cl)=C1Br JFRNHGWPQJPTCO-UHFFFAOYSA-N 0.000 description 4
- PNZXJYMLKBWYNE-UHFFFAOYSA-N 5-bromo-4-methoxy-6-(trifluoromethyl)pyrimidine Chemical compound COC1=NC=NC(C(F)(F)F)=C1Br PNZXJYMLKBWYNE-UHFFFAOYSA-N 0.000 description 4
- OPWVMJDFQNRXIG-UHFFFAOYSA-N 5-chloro-1-phenyl-3-(trifluoromethyl)pyrazole-4-carbaldehyde Chemical compound ClC1=C(C=O)C(C(F)(F)F)=NN1C1=CC=CC=C1 OPWVMJDFQNRXIG-UHFFFAOYSA-N 0.000 description 4
- 241001621841 Alopecurus myosuroides Species 0.000 description 4
- 235000004135 Amaranthus viridis Nutrition 0.000 description 4
- 244000055702 Amaranthus viridis Species 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 235000007320 Avena fatua Nutrition 0.000 description 4
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- 240000005979 Hordeum vulgare Species 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 241000533293 Sesbania emerus Species 0.000 description 4
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 description 4
- 238000012790 confirmation Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 125000000842 isoxazolyl group Chemical group 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000007774 longterm Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- XUPZIEHQZDPOFO-UHFFFAOYSA-N (5-chloro-3-methyl-1,2-thiazol-4-yl)methanol Chemical compound CC1=NSC(Cl)=C1CO XUPZIEHQZDPOFO-UHFFFAOYSA-N 0.000 description 3
- CPOIHVJSPQWRRN-UHFFFAOYSA-N 3-(bromomethyl)-4-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=NC=C1CBr CPOIHVJSPQWRRN-UHFFFAOYSA-N 0.000 description 3
- IOWBZFBCKKSZRD-UHFFFAOYSA-N 3-[(2,6-difluorophenyl)methylsulfinyl]-5-ethyl-5-methyl-4h-1,2-oxazole Chemical compound O1C(CC)(C)CC(S(=O)CC=2C(=CC=CC=2F)F)=N1 IOWBZFBCKKSZRD-UHFFFAOYSA-N 0.000 description 3
- RRMOQGLBISUPSX-UHFFFAOYSA-N 3-[(3,5-dichloro-1-ethylpyrazol-4-yl)methylsulfanyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CCN1N=C(Cl)C(CSC=2CC(C)(C)ON=2)=C1Cl RRMOQGLBISUPSX-UHFFFAOYSA-N 0.000 description 3
- IAQGHFFZDUCHPA-UHFFFAOYSA-N 3-[(5-chloro-3-methyl-1,2-thiazol-4-yl)methylsulfanyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CC1=NSC(Cl)=C1CSC1=NOC(C)(C)C1 IAQGHFFZDUCHPA-UHFFFAOYSA-N 0.000 description 3
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- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000004500 isothiazol-4-yl group Chemical group S1N=CC(=C1)* 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- RJQVQDYEBIHZKH-UHFFFAOYSA-N methyl 2-chloro-4-methylpyridine-3-carboxylate Chemical compound COC(=O)C1=C(C)C=CN=C1Cl RJQVQDYEBIHZKH-UHFFFAOYSA-N 0.000 description 1
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 description 1
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DDPWVABNMBRBFI-UHFFFAOYSA-N tert-butylhydrazine;hydron;chloride Chemical compound Cl.CC(C)(C)NN DDPWVABNMBRBFI-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 244000277848 tiririca Species 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000009736 wetting Methods 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002230028 | 2002-08-07 | ||
| PCT/JP2003/010073 WO2004014138A1 (ja) | 2002-08-07 | 2003-08-07 | 除草剤組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR0313241A BR0313241A (pt) | 2005-08-09 |
| BR0313241B1 true BR0313241B1 (pt) | 2018-01-09 |
Family
ID=31711670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0313241A BR0313241B1 (pt) | 2002-08-07 | 2003-08-07 | composição herbicida |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7833939B2 (enExample) |
| JP (1) | JP4789101B2 (enExample) |
| AR (1) | AR040809A1 (enExample) |
| AU (1) | AU2003254863A1 (enExample) |
| BR (1) | BR0313241B1 (enExample) |
| IN (2) | IN2005KN00058A (enExample) |
| MY (1) | MY132698A (enExample) |
| PA (1) | PA8579501A1 (enExample) |
| PE (1) | PE20040373A1 (enExample) |
| PL (1) | PL207304B1 (enExample) |
| TW (1) | TWI309967B (enExample) |
| UA (1) | UA78071C2 (enExample) |
| UY (1) | UY27909A1 (enExample) |
| WO (1) | WO2004014138A1 (enExample) |
Families Citing this family (89)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10163079A1 (de) * | 2001-12-20 | 2003-07-03 | Basf Ag | Verfahren zur Verbesserung des Pflanzenwachstums durch Applikation einer Mischung aus Schwefel und Komplexbildner |
| JP4744119B2 (ja) * | 2003-10-20 | 2011-08-10 | クミアイ化学工業株式会社 | 除草剤組成物 |
| JP4621939B2 (ja) | 2004-03-31 | 2011-02-02 | イハラケミカル工業株式会社 | ５−ヒドロキシ−４−チオメチルピラゾール化合物の製造方法 |
| JP2007246396A (ja) * | 2004-04-28 | 2007-09-27 | Ihara Chem Ind Co Ltd | ５−ジフルオロメトキシ−４−チオメチルピラゾール化合物の製造方法 |
| JP4980209B2 (ja) * | 2004-04-30 | 2012-07-18 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | 除草剤組成物 |
| ES2333977T3 (es) * | 2004-10-05 | 2010-03-03 | Syngenta Limited | Derivados de isoxazolina y su uso como herbicidas. |
| MY144905A (en) * | 2005-03-17 | 2011-11-30 | Basf Ag | Herbicidal compositions based on 3-phenyluracils and 3-sulfonylisoxazolines |
| GB0505645D0 (en) * | 2005-03-18 | 2005-04-27 | Syngenta Participations Ag | Herbicidal composition |
| DE102005031412A1 (de) * | 2005-07-06 | 2007-01-11 | Bayer Cropscience Gmbh | 3-[1-Halo-1-aryl-methan-sulfonyl]-und 3-[1-Halo-1-heteroaryl-methan-sulfonyl]-isoxazolin-Derivate, Verfahren zu deren Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| WO2007003296A1 (de) * | 2005-07-06 | 2007-01-11 | Bayer Cropscience Ag | Herbizid-safener-kombination |
| WO2007006409A2 (de) * | 2005-07-07 | 2007-01-18 | Bayer Cropscience Ag | Herbizid-safener-kombination |
| GB0526044D0 (en) * | 2005-12-21 | 2006-02-01 | Syngenta Ltd | Novel herbicides |
| GB0603891D0 (en) * | 2006-02-27 | 2006-04-05 | Syngenta Ltd | Novel herbicides |
| WO2007147828A1 (en) * | 2006-06-20 | 2007-12-27 | Basf Se | Herbicidal compositions comprising a 3-heterocyclyl-substituted benzoyl compound |
| WO2008073369A1 (en) * | 2006-12-12 | 2008-06-19 | E. I. Du Pont De Nemours And Company | Herbicidal mixtures |
| US8110530B2 (en) | 2006-12-21 | 2012-02-07 | Kumiai Chemical Industry Co., Ltd. | Herbicidal composition |
| AU2012202063B9 (en) * | 2006-12-21 | 2013-07-18 | Kumiai Chemical Industry Co., Ltd. | Herbicide composition |
| CL2008000376A1 (es) * | 2007-02-09 | 2008-08-18 | Du Pont | Compuestos derivados de n-oxidos de piridina; composicion herbicida; y metodo para controlar el crecimiento de vegetacion indeseada. |
| EP2065373A1 (de) * | 2007-11-30 | 2009-06-03 | Bayer CropScience AG | Chirale 3-(Benzylsulfinyl)-5,5-dimethyl-4,5-dihydroisoxazol-Derivate und 5,5-Dimethyl-3-[(1H-pyrazol-4-ylmethyl) sulfinyl]-4,5-dihydroisoxazol-Derivate, Verfahren zu deren Herstellung sowie deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| EP2092825A1 (de) | 2008-02-21 | 2009-08-26 | Bayer CropScience Aktiengesellschaft | Herbizid-Kombinationen enthaltend ein Herbizid der Klasse der Diamino-s-triazine |
| BRPI0910335B1 (pt) * | 2008-03-10 | 2018-01-09 | Basf Se | Composição herbicida, uso da mesma, método para controlar vegetação indesejável, e, formulação herbicida |
| CN101969777B (zh) * | 2008-03-11 | 2014-06-18 | 巴斯夫欧洲公司 | 包含派罗克杀草砜的除草组合物 |
| EP2280606A2 (en) * | 2008-03-12 | 2011-02-09 | Basf Se | Herbicidal compositions comprising pyroxasulfone |
| TW200944127A (en) * | 2008-03-14 | 2009-11-01 | Basf Se | Herbicidal compositions comprising pyroxasulfone |
| AU2009226931A1 (en) * | 2008-03-17 | 2009-09-24 | Basf Se | Herbicidal compositions comprising pyroxasulfone V |
| CA2717018A1 (en) * | 2008-03-18 | 2009-09-24 | Basf Se | Herbicidal compositions comprising pyroxasulfone vi |
| WO2009116151A1 (ja) * | 2008-03-19 | 2009-09-24 | アグロカネショウ株式会社 | １-フェニル-５-ジフルオロメチルピラゾール-４-カルボキサミド誘導体及びこれを有効成分とする除草剤 |
| WO2009115434A2 (en) * | 2008-03-19 | 2009-09-24 | Basf Se | Herbicidal compositions comprising pyroxasulfone ix |
| EA019676B1 (ru) * | 2008-03-20 | 2014-05-30 | Басф Се | Гербицидные композиции, содержащие пироксасульфон iv |
| WO2009115603A2 (en) * | 2008-03-21 | 2009-09-24 | Basf Se | Herbicidal compositions comprising pyroxasulfone viii |
| AU2009248755B2 (en) * | 2008-05-21 | 2015-04-09 | Basf Se | Herbicidal composition comprising glyphosate, glufosinate or their salts |
| WO2009158258A1 (en) * | 2008-06-25 | 2009-12-30 | E. I. Du Pont De Nemours And Company | Herbicidal dihydro oxo six-membered azinyl isoxazolines |
| CN102369171B (zh) * | 2009-04-15 | 2013-12-11 | 组合化学工业株式会社 | 含有除草农药的粒状肥料 |
| EP2251331A1 (en) | 2009-05-15 | 2010-11-17 | Bayer CropScience AG | Fungicide pyrazole carboxamides derivatives |
| AR076839A1 (es) | 2009-05-15 | 2011-07-13 | Bayer Cropscience Ag | Derivados fungicidas de pirazol carboxamidas |
| EP2325173A1 (de) | 2009-11-19 | 2011-05-25 | Bayer CropScience AG | Verfahren zum Herstellen von 5-Fluor-1-alkyl-3-fluoralkyl-1H-pyrazol-4-carbonsäurechloriden |
| ES2528646T3 (es) * | 2010-05-20 | 2015-02-11 | Bayer Intellectual Property Gmbh | Procedimiento para la fabricación de 1-alquil-3-difluorometil-5-hidroxipirazoles |
| US8653114B2 (en) | 2010-06-03 | 2014-02-18 | Bayer Intellectual Property Gmbh | O-cyclopropylcyclohexyl-carboxanilides and their use as fungicides |
| WO2011151369A1 (en) | 2010-06-03 | 2011-12-08 | Bayer Cropscience Ag | N-[(het)arylethyl)] pyrazole(thio)carboxamides and their heterosubstituted analogues |
| MX2012013896A (es) | 2010-06-03 | 2012-12-17 | Bayer Cropscience Ag | N-[(het)arilalquil)]pirazol(tio)carboxamidas y sus analogos heterosustituidos. |
| CN101971818A (zh) * | 2010-07-14 | 2011-02-16 | 湖北奥士特奥农药产品研发有限公司 | 二甲戊灵与扑草净二元复配制成的除草剂及其制备方法 |
| JP2013541554A (ja) | 2010-10-21 | 2013-11-14 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | Ｎ−ベンジルヘテロ環式カルボキサミド類 |
| CN103298802B (zh) | 2010-11-02 | 2016-06-08 | 拜耳知识产权有限责任公司 | N-杂芳基甲基吡唑基羧酰胺 |
| JP5860471B2 (ja) | 2010-11-15 | 2016-02-16 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | Ｎ−アリールピラゾール（チオ）カルボキサミド類 |
| CN103339104A (zh) | 2010-11-15 | 2013-10-02 | 拜耳知识产权有限责任公司 | 十氢-1,4-桥亚甲基萘甲酰胺 |
| WO2012065947A1 (en) | 2010-11-15 | 2012-05-24 | Bayer Cropscience Ag | 5-halogenopyrazolecarboxamides |
| US20130231303A1 (en) | 2010-11-15 | 2013-09-05 | Bayer Intellectual Property Gmbh | 5-halogenopyrazole(thio)carboxamides |
| JP5927055B2 (ja) | 2011-06-24 | 2016-05-25 | 石原産業株式会社 | 除草組成物 |
| JP5964441B2 (ja) * | 2011-10-18 | 2016-08-03 | エフ エム シー コーポレーションＦｍｃ Ｃｏｒｐｏｒａｔｉｏｎ | フュームド酸化アルミニウムを含む安定な調合物 |
| US8962525B2 (en) * | 2011-10-18 | 2015-02-24 | Fmc Corporation | Stable formulations containing fumed aluminum oxide |
| EP2662363A1 (en) | 2012-05-09 | 2013-11-13 | Bayer CropScience AG | 5-Halogenopyrazole biphenylcarboxamides |
| EP2662370A1 (en) | 2012-05-09 | 2013-11-13 | Bayer CropScience AG | 5-Halogenopyrazole benzofuranyl carboxamides |
| EP2662360A1 (en) | 2012-05-09 | 2013-11-13 | Bayer CropScience AG | 5-Halogenopyrazole indanyl carboxamides |
| EP2662364A1 (en) | 2012-05-09 | 2013-11-13 | Bayer CropScience AG | Pyrazole tetrahydronaphthyl carboxamides |
| EP2662361A1 (en) | 2012-05-09 | 2013-11-13 | Bayer CropScience AG | Pyrazol indanyl carboxamides |
| EP2662362A1 (en) | 2012-05-09 | 2013-11-13 | Bayer CropScience AG | Pyrazole indanyl carboxamides |
| ES2625805T3 (es) | 2012-05-24 | 2017-07-20 | Bayer Cropscience Ag | Composiciones herbicidas que contienen amidas de ácido N-(tetrazol-5-il)arilcarboxílico |
| UA118765C2 (uk) | 2013-08-09 | 2019-03-11 | Байєр Кропсайєнс Акцієнгезелльшафт | Третинні гербіцидні комбінації, що містять дві сульфонілсечовини |
| EP3060057A1 (de) | 2013-10-25 | 2016-08-31 | Bayer CropScience Aktiengesellschaft | Herbizide zusammensetzungen enthaltend n-(1,3,4-oxadiazol-2-yl)arylcarbon-säureamide |
| CN104478829A (zh) * | 2014-11-12 | 2015-04-01 | 浙江中山化工集团股份有限公司 | 一种苯达松二甲胺盐原药的制备方法 |
| CN106259362A (zh) * | 2015-06-09 | 2017-01-04 | 江苏龙灯化学有限公司 | 一种增效除草组合物 |
| AU2016200560B1 (en) * | 2016-01-29 | 2016-12-15 | Rotam Agrochem International Company Limited | A synergistic herbicidal composition |
| AU2016200564B1 (en) * | 2016-01-29 | 2016-12-15 | Rotam Agrochem International Company Limited | A synergistic herbicidal composition |
| CN106614630A (zh) * | 2016-09-18 | 2017-05-10 | 辽宁海佳农化有限公司 | 一种除草剂及其制备方法 |
| EP3338551A1 (en) | 2016-12-21 | 2018-06-27 | Bayer CropScience Aktiengesellschaft | Herbicide combinations |
| EP3378315A1 (de) | 2017-03-24 | 2018-09-26 | Bayer CropScience Aktiengesellschaft | Herbizide mischungen enthaltend 2-[2,4-dichlorphenyl)methyl]-4,4-dimethyl-3-isoxazolidinon |
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| WO2023194957A1 (en) * | 2022-04-08 | 2023-10-12 | Upl Limited | A process for preparation of 3-[5-(difluoromethoxy)-1- methyl-3-(trifluoromethyl)pyrazol-4- ylmethylsulfonyl]-4,5-dihydro-5,5-dimethyl-1,2-oxazole and its intermediates |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2677221B1 (fr) * | 1991-06-10 | 1993-10-15 | Roquette Freres | Composition phytosanitaire, son procede de preparation et son utilisation, en particulier pour lutter contre les mauvaises herbes. |
| JP3810838B2 (ja) | 1994-12-12 | 2006-08-16 | 三共アグロ株式会社 | 除草性イソオキサゾリン誘導体 |
| JPH09328483A (ja) * | 1996-06-11 | 1997-12-22 | Sankyo Co Ltd | 除草性イソオキサゾリン誘導体 |
| IT1292088B1 (it) * | 1997-06-05 | 1999-01-25 | Isagro Ricerca Srl | Composizioni erbicide |
| UA70949C2 (uk) | 1998-06-16 | 2004-11-15 | Басф Акцієнгезелльшафт | Гербіцидна суміш із синергічною дією, гербіцидний засіб та спосіб боротьби з небажаною рослинністю |
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| DE60238194D1 (de) * | 2001-06-21 | 2010-12-16 | Kumiai Chemical Industry Co | Isoxazolinderivate und herbizide |
| WO2003010165A1 (en) | 2001-07-24 | 2003-02-06 | Kumiai Chemical Industry Co., Ltd. | Isoxazoline derivatives and herbicides for agricultural and horticultural use |
| DE10145019A1 (de) * | 2001-09-13 | 2003-04-03 | Bayer Cropscience Gmbh | Kombinationen aus Herbiziden und Safenern |
| RS51323B (sr) * | 2004-09-03 | 2010-12-31 | Syngenta Limited | Derivati izoksazolona i njihova upotreba kao herbicida |
-
2003
- 2003-07-08 UA UAA200500938A patent/UA78071C2/uk unknown
- 2003-07-24 TW TW092120271A patent/TWI309967B/zh not_active IP Right Cessation
- 2003-07-30 MY MYPI20032896A patent/MY132698A/en unknown
- 2003-07-31 UY UY27909A patent/UY27909A1/es not_active IP Right Cessation
- 2003-08-05 PE PE2003000771A patent/PE20040373A1/es active IP Right Grant
- 2003-08-05 PA PA20038579501A patent/PA8579501A1/es unknown
- 2003-08-06 AR AR20030102825A patent/AR040809A1/es active IP Right Grant
- 2003-08-07 AU AU2003254863A patent/AU2003254863A1/en not_active Abandoned
- 2003-08-07 PL PL375112A patent/PL207304B1/pl unknown
- 2003-08-07 JP JP2004527360A patent/JP4789101B2/ja not_active Expired - Fee Related
- 2003-08-07 US US10/521,755 patent/US7833939B2/en active Active
- 2003-08-07 BR BRPI0313241A patent/BR0313241B1/pt active IP Right Grant
- 2003-08-07 WO PCT/JP2003/010073 patent/WO2004014138A1/ja not_active Ceased
-
2005
- 2005-09-16 IN IN58KON2005 patent/IN2005KN00058A/en unknown
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2007
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|---|---|
| JPWO2004014138A1 (ja) | 2005-11-24 |
| UA78071C2 (en) | 2007-02-15 |
| JP4789101B2 (ja) | 2011-10-12 |
| AU2003254863A1 (en) | 2004-02-25 |
| MY132698A (en) | 2007-10-31 |
| WO2004014138A1 (ja) | 2004-02-19 |
| US20050256004A1 (en) | 2005-11-17 |
| BR0313241A (pt) | 2005-08-09 |
| US7833939B2 (en) | 2010-11-16 |
| TWI309967B (en) | 2009-05-21 |
| PE20040373A1 (es) | 2004-08-27 |
| PL375112A1 (en) | 2005-11-28 |
| PL207304B1 (pl) | 2010-11-30 |
| TW200406154A (en) | 2004-05-01 |
| UY27909A1 (es) | 2004-02-27 |
| IN2007KO02033A (enExample) | 2009-04-10 |
| IN2005KN00058A (enExample) | 2006-01-06 |
| AR040809A1 (es) | 2005-04-20 |
| PA8579501A1 (es) | 2005-02-04 |
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