UA78071C2 - Herbicidal composition - Google Patents
Herbicidal composition Download PDFInfo
- Publication number
- UA78071C2 UA78071C2 UAA200500938A UA2005000938A UA78071C2 UA 78071 C2 UA78071 C2 UA 78071C2 UA A200500938 A UAA200500938 A UA A200500938A UA 2005000938 A UA2005000938 A UA 2005000938A UA 78071 C2 UA78071 C2 UA 78071C2
- Authority
- UA
- Ukraine
- Prior art keywords
- group
- reaction
- mmol
- solution
- methyl
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 214
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 74
- 150000001875 compounds Chemical class 0.000 claims abstract description 94
- 150000002547 isoxazolines Chemical class 0.000 claims abstract description 17
- -1 1-methoxyiminoethyl Chemical group 0.000 claims description 152
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 238000006467 substitution reaction Methods 0.000 claims description 14
- 239000003905 agrochemical Substances 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004500 isothiazol-4-yl group Chemical group S1N=CC(=C1)* 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 22
- 239000004009 herbicide Substances 0.000 abstract description 11
- 239000004480 active ingredient Substances 0.000 abstract description 9
- 239000000243 solution Substances 0.000 description 239
- 238000006243 chemical reaction Methods 0.000 description 211
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 202
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 177
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 174
- 239000007864 aqueous solution Substances 0.000 description 151
- 239000002904 solvent Substances 0.000 description 148
- 238000002360 preparation method Methods 0.000 description 123
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 119
- 238000005292 vacuum distillation Methods 0.000 description 118
- 239000011541 reaction mixture Substances 0.000 description 109
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 106
- 239000012044 organic layer Substances 0.000 description 102
- 239000011780 sodium chloride Substances 0.000 description 101
- 238000005481 NMR spectroscopy Methods 0.000 description 77
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 74
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 68
- 125000000217 alkyl group Chemical group 0.000 description 58
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 50
- 238000001816 cooling Methods 0.000 description 46
- 239000000741 silica gel Substances 0.000 description 44
- 229910002027 silica gel Inorganic materials 0.000 description 44
- 238000004440 column chromatography Methods 0.000 description 41
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-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 38
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 37
- 239000012046 mixed solvent Substances 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 32
- 238000002844 melting Methods 0.000 description 31
- 230000008018 melting Effects 0.000 description 31
- 239000013078 crystal Substances 0.000 description 30
- 125000000623 heterocyclic group Chemical group 0.000 description 30
- 229910052757 nitrogen Inorganic materials 0.000 description 29
- 241000196324 Embryophyta Species 0.000 description 28
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 28
- 238000010411 cooking Methods 0.000 description 28
- 125000004433 nitrogen atom Chemical group N* 0.000 description 28
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 27
- 125000001188 haloalkyl group Chemical group 0.000 description 27
- 125000003118 aryl group Chemical group 0.000 description 26
- 125000002252 acyl group Chemical group 0.000 description 24
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 23
- 239000000126 substance Substances 0.000 description 23
- 125000000753 cycloalkyl group Chemical group 0.000 description 22
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 21
- 125000005843 halogen group Chemical group 0.000 description 20
- 229910000027 potassium carbonate Inorganic materials 0.000 description 19
- 235000011181 potassium carbonates Nutrition 0.000 description 19
- 239000000843 powder Substances 0.000 description 19
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 17
- 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- 125000004414 alkyl thio group Chemical group 0.000 description 14
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 240000008042 Zea mays Species 0.000 description 11
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 11
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 11
- 235000005822 corn Nutrition 0.000 description 11
- 125000003342 alkenyl group Chemical group 0.000 description 10
- 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
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 10
- 239000002689 soil Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 9
- 244000062793 Sorghum vulgare Species 0.000 description 9
- 125000000304 alkynyl group Chemical group 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 8
- 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 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
- 239000005562 Glyphosate Substances 0.000 description 8
- 240000007594 Oryza sativa Species 0.000 description 8
- 235000007164 Oryza sativa Nutrition 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 235000009566 rice Nutrition 0.000 description 8
- 239000004563 wettable powder Substances 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
- 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 6
- GKZPFZFOBISMIQ-UHFFFAOYSA-N 3-[[5-(difluoromethoxy)-1-ethyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfanyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CCN1N=C(C(F)(F)F)C(CSC=2CC(C)(C)ON=2)=C1OC(F)F GKZPFZFOBISMIQ-UHFFFAOYSA-N 0.000 description 6
- NMZGFTTXPHXOQR-UHFFFAOYSA-N 3-ethylsulfonyl-5,5-dimethyl-4h-1,2-oxazole Chemical compound CCS(=O)(=O)C1=NOC(C)(C)C1 NMZGFTTXPHXOQR-UHFFFAOYSA-N 0.000 description 6
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 6
- 239000005561 Glufosinate Substances 0.000 description 6
- 239000005573 Linuron Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 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
- 230000035784 germination Effects 0.000 description 6
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 6
- 229940097068 glyphosate Drugs 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 6
- ZNKXTIAQRUWLRL-UHFFFAOYSA-M sodium;sulfane;hydroxide Chemical compound O.[Na+].[SH-] ZNKXTIAQRUWLRL-UHFFFAOYSA-M 0.000 description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 5
- 235000018185 Betula X alpestris Nutrition 0.000 description 5
- 235000018212 Betula X uliginosa Nutrition 0.000 description 5
- 240000006162 Chenopodium quinoa Species 0.000 description 5
- 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 description 5
- 235000010469 Glycine max Nutrition 0.000 description 5
- 244000068988 Glycine max Species 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 5
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 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
- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 125000004434 sulfur atom Chemical group 0.000 description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 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
- 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
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 4
- 244000025254 Cannabis sativa Species 0.000 description 4
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 4
- 235000007542 Cichorium intybus Nutrition 0.000 description 4
- 244000298479 Cichorium intybus Species 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 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
- 241000287828 Gallus gallus Species 0.000 description 4
- 241000219146 Gossypium Species 0.000 description 4
- 240000005979 Hordeum vulgare Species 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 4
- 235000021536 Sugar beet Nutrition 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000003085 diluting agent Substances 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
- KACZQOKEFKFNDB-UHFFFAOYSA-N ethyl 1h-pyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NNC=1 KACZQOKEFKFNDB-UHFFFAOYSA-N 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
- 239000007788 liquid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 235000019713 millet Nutrition 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 125000004149 thio group Chemical group *S* 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- FPRCFSPOHNIVJZ-UHFFFAOYSA-N 1-tert-butyl-5-chloro-3-(trifluoromethyl)pyrazole-4-carbaldehyde Chemical compound CC(C)(C)N1N=C(C(F)(F)F)C(C=O)=C1Cl FPRCFSPOHNIVJZ-UHFFFAOYSA-N 0.000 description 3
- WKMFERCWDKFEAT-UHFFFAOYSA-N 1-tert-butyl-5-methoxy-3-(trifluoromethyl)pyrazole Chemical compound COC1=CC(C(F)(F)F)=NN1C(C)(C)C WKMFERCWDKFEAT-UHFFFAOYSA-N 0.000 description 3
- PSQCMVQGPMFFCX-UHFFFAOYSA-N 2-phenyl-5-(trifluoromethyl)-1h-pyrazol-3-one Chemical compound N1C(C(F)(F)F)=CC(=O)N1C1=CC=CC=C1 PSQCMVQGPMFFCX-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
- NUMZFVAPMXERTH-UHFFFAOYSA-N 3-[[1-tert-butyl-5-chloro-3-(trifluoromethyl)pyrazol-4-yl]methylsulfanyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CC(C)(C)N1N=C(C(F)(F)F)C(CSC=2CC(C)(C)ON=2)=C1Cl NUMZFVAPMXERTH-UHFFFAOYSA-N 0.000 description 3
- YCRLRTYMUYXXLF-UHFFFAOYSA-N 3-[[3-ethoxy-1-methyl-5-(trifluoromethyl)pyrazol-4-yl]methylsulfanyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CCOC1=NN(C)C(C(F)(F)F)=C1CSC1=NOC(C)(C)C1 YCRLRTYMUYXXLF-UHFFFAOYSA-N 0.000 description 3
- ZJXURWCXFFNTNW-UHFFFAOYSA-N 3-[[5-(2-chlorophenoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfanyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound C=1C=CC=C(Cl)C=1OC=1N(C)N=C(C(F)(F)F)C=1CSC1=NOC(C)(C)C1 ZJXURWCXFFNTNW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- AAFDLVBWHFIBDM-UHFFFAOYSA-N 3-[[5-chloro-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)=C1Cl AAFDLVBWHFIBDM-UHFFFAOYSA-N 0.000 description 3
- NHWVRKZDJZIILW-UHFFFAOYSA-N 3-[[5-chloro-1-phenyl-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=2C=CC=CC=2)C(F)(F)F)=N1 NHWVRKZDJZIILW-UHFFFAOYSA-N 0.000 description 3
- XHZSQGFKYZYIFE-UHFFFAOYSA-N 3-[[5-chloro-3-(difluoromethyl)-1-methylpyrazol-4-yl]methylsulfanyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CN1N=C(C(F)F)C(CSC=2CC(C)(C)ON=2)=C1Cl XHZSQGFKYZYIFE-UHFFFAOYSA-N 0.000 description 3
- 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 3
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (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 (1)
| Publication Number | Publication Date |
|---|---|
| UA78071C2 true UA78071C2 (en) | 2007-02-15 |
Family
ID=31711670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA200500938A UA78071C2 (en) | 2002-08-07 | 2003-07-08 | Herbicidal composition |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7833939B2 (ko) |
| JP (1) | JP4789101B2 (ko) |
| AR (1) | AR040809A1 (ko) |
| AU (1) | AU2003254863A1 (ko) |
| BR (1) | BR0313241B1 (ko) |
| IN (2) | IN2005KO00058A (ko) |
| MY (1) | MY132698A (ko) |
| PA (1) | PA8579501A1 (ko) |
| PE (1) | PE20040373A1 (ko) |
| PL (1) | PL207304B1 (ko) |
| TW (1) | TWI309967B (ko) |
| UA (1) | UA78071C2 (ko) |
| UY (1) | UY27909A1 (ko) |
| WO (1) | WO2004014138A1 (ko) |
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| 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 |
| ES2297709T3 (es) * | 2004-04-30 | 2008-05-01 | Syngenta Participations Ag | Composicion herbicida. |
| ATE450517T1 (de) * | 2004-10-05 | 2009-12-15 | Syngenta Ltd | Isoxazolinderivate und ihre verwendung als herbizide |
| 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 |
| AU2012202060B2 (en) * | 2006-12-21 | 2013-06-27 | Kumiai Chemical Industry Co., Ltd. | Herbicide composition |
| US8110530B2 (en) * | 2006-12-21 | 2012-02-07 | Kumiai Chemical Industry Co., Ltd. | Herbicidal 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 |
| UA102685C2 (en) * | 2008-03-10 | 2013-08-12 | Басф Се | Herbicidal compositions comprising pyroxasulfone |
| AU2009224674B2 (en) * | 2008-03-11 | 2014-04-03 | Basf Se | Herbicidal compositions comprising pyroxasulfone |
| CN102083316A (zh) * | 2008-03-12 | 2011-06-01 | 巴斯夫欧洲公司 | 包含派罗克杀草砜的除草组合物 |
| TW200944127A (en) * | 2008-03-14 | 2009-11-01 | Basf Se | Herbicidal compositions comprising pyroxasulfone |
| EA201001452A1 (ru) * | 2008-03-17 | 2011-06-30 | Басф Се | Гербицидные композиции, содержащие пироксасульфон v |
| AU2009226861A1 (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 |
| AU2009226874B2 (en) * | 2008-03-20 | 2015-02-19 | Basf Se | Herbicidal compositions comprising pyroxasulfone IV |
| WO2009115603A2 (en) * | 2008-03-21 | 2009-09-24 | Basf Se | Herbicidal compositions comprising pyroxasulfone viii |
| BR122017015607B1 (pt) | 2008-05-21 | 2024-02-06 | Basf Se | Composição herbicida, e, métodos para controlar vegetação indesejável e para tratamento de queimada de vegetação indesejável em culturas |
| WO2009158258A1 (en) * | 2008-06-25 | 2009-12-30 | E. I. Du Pont De Nemours And Company | Herbicidal dihydro oxo six-membered azinyl isoxazolines |
| AU2010237952B2 (en) * | 2009-04-15 | 2014-05-01 | Kumiai Chemical Industry Co., Ltd. | Granular fertilizer containing herbicidal agrochemical |
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| 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 |
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| MX2013005407A (es) | 2010-11-15 | 2013-07-03 | Bayer Ip Gmbh | 5-halopirazolcarboxamidas. |
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| CN109836391B (zh) * | 2017-11-24 | 2019-12-27 | 东莞市东阳光农药研发有限公司 | 异噁唑啉衍生物及其在农业中的应用 |
| CN108184863A (zh) * | 2017-12-23 | 2018-06-22 | 山东滨农科技有限公司 | 一种含氰草津的除草剂组合物 |
| CN108294016A (zh) * | 2018-02-02 | 2018-07-20 | 河北中天邦正生物科技股份公司 | 一种农药组合物及其应用 |
| CN110511216B (zh) * | 2018-05-22 | 2020-09-11 | 东莞市东阳光农药研发有限公司 | 异噁唑啉衍生物及其在农业中的应用 |
| CN109845748A (zh) * | 2019-01-31 | 2019-06-07 | 山东德浩化学有限公司 | 一种含有砜吡草唑和二氯喹啉酸的除草组合物及其应用 |
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| EP4053125A4 (en) * | 2019-10-31 | 2023-07-05 | Kumiai Chemical Industry Co., Ltd. | HERBICIDE AND METHOD OF MANUFACTURE OF AN INTERMEDIATE THEREOF |
| CN112794846B (zh) * | 2019-11-14 | 2022-09-20 | 宁夏苏融达化工有限公司 | 乙基异噁唑啉类衍生物及其应用 |
| CN113620941B (zh) * | 2020-05-07 | 2023-07-14 | 宁夏苏融达化工有限公司 | 环丙基-吡唑衍生物及其在农业中的应用 |
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| WO2022233129A1 (en) | 2021-05-05 | 2022-11-10 | Fujian Yongjing Technology Co., Ltd | New process for the synthesis of 5-fluoro-3- (difuoromethyl) -5-fluoro-1-methyl-1h-pyrazole-4-carboxylic acid derivatives and the free acid thereof |
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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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| CN114957233A (zh) * | 2022-07-05 | 2022-08-30 | 淄博新农基作物科学有限公司 | 砜吡草唑及其制备方法 |
| WO2024012913A1 (en) | 2022-07-13 | 2024-01-18 | BASF Agro B.V. | Herbicidal eode formulation comprising several active ingredients |
| WO2024042134A1 (en) | 2022-08-26 | 2024-02-29 | BASF Agro B.V. | Aqueous herbicide formulations |
| CN116514792B (zh) * | 2023-07-04 | 2023-10-27 | 潍坊新绿化工有限公司 | 一种砜吡草唑的制备方法 |
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| 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. |
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| 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 |
| MX217057B (es) * | 1998-06-16 | 2003-10-20 | Basf Ag | Mezclas herbicidas de accion sinergica |
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| JP4317445B2 (ja) * | 2001-06-21 | 2009-08-19 | クミアイ化学工業株式会社 | イソオキサゾリン誘導体及び除草剤 |
| WO2003010165A1 (fr) * | 2001-07-24 | 2003-02-06 | Kumiai Chemical Industry Co., Ltd. | Derives d'isoxazoline et herbicides destines a un usage agricole ou horticole |
| DE10145019A1 (de) * | 2001-09-13 | 2003-04-03 | Bayer Cropscience Gmbh | Kombinationen aus Herbiziden und Safenern |
| BRPI0514880A (pt) * | 2004-09-03 | 2008-06-24 | Syngenta Ltd | composto, processo para a preparação do mesmo, composição herbicida, e, método para controlar gramas e ervas daninhas em culturas de plantas úteis |
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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 WO PCT/JP2003/010073 patent/WO2004014138A1/ja active Application Filing
- 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
-
2005
- 2005-01-19 IN IN58KO2005 patent/IN2005KO00058A/en unknown
-
2007
- 2007-06-05 IN IN2033KO2007 patent/IN2007KO02033A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IN2007KO02033A (ko) | 2009-04-10 |
| US7833939B2 (en) | 2010-11-16 |
| AR040809A1 (es) | 2005-04-20 |
| UY27909A1 (es) | 2004-02-27 |
| PA8579501A1 (es) | 2005-02-04 |
| PE20040373A1 (es) | 2004-08-27 |
| AU2003254863A1 (en) | 2004-02-25 |
| BR0313241A (pt) | 2005-08-09 |
| JPWO2004014138A1 (ja) | 2005-11-24 |
| JP4789101B2 (ja) | 2011-10-12 |
| TWI309967B (en) | 2009-05-21 |
| BR0313241B1 (pt) | 2018-01-09 |
| PL375112A1 (en) | 2005-11-28 |
| US20050256004A1 (en) | 2005-11-17 |
| TW200406154A (en) | 2004-05-01 |
| IN2005KO00058A (ko) | 2006-01-06 |
| PL207304B1 (pl) | 2010-11-30 |
| MY132698A (en) | 2007-10-31 |
| WO2004014138A1 (ja) | 2004-02-19 |
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