PL207304B1 - Kompozycja chwastobójcza - Google Patents
Kompozycja chwastobójczaInfo
- Publication number
- PL207304B1 PL207304B1 PL375112A PL37511203A PL207304B1 PL 207304 B1 PL207304 B1 PL 207304B1 PL 375112 A PL375112 A PL 375112A PL 37511203 A PL37511203 A PL 37511203A PL 207304 B1 PL207304 B1 PL 207304B1
- Authority
- PL
- Poland
- Prior art keywords
- solution
- mmol
- dimethyl
- mixture
- isoxazoline
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 202
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 64
- 239000004009 herbicide Substances 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 150000002547 isoxazolines Chemical class 0.000 claims abstract description 13
- -1 prosulfuronral Chemical compound 0.000 claims description 54
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 claims description 14
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 7
- 239000003905 agrochemical Substances 0.000 claims description 6
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 239000005562 Glyphosate Substances 0.000 claims description 4
- 239000005573 Linuron Substances 0.000 claims description 4
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 4
- 229940097068 glyphosate Drugs 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 claims description 4
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000005561 Glufosinate Substances 0.000 claims description 3
- CLQMBPJKHLGMQK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-UHFFFAOYSA-N 0.000 claims description 2
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005476 Bentazone Substances 0.000 claims description 2
- 239000005500 Clopyralid Substances 0.000 claims description 2
- 239000005504 Dicamba Substances 0.000 claims description 2
- 239000005507 Diflufenican Substances 0.000 claims description 2
- 239000005532 Flumioxazine Substances 0.000 claims description 2
- XVOKUMIPKHGGTN-UHFFFAOYSA-N Imazethapyr Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 XVOKUMIPKHGGTN-UHFFFAOYSA-N 0.000 claims description 2
- 239000005571 Isoxaflutole Substances 0.000 claims description 2
- 239000005578 Mesotrione Substances 0.000 claims description 2
- 239000005591 Pendimethalin Substances 0.000 claims description 2
- 239000005616 Rimsulfuron Substances 0.000 claims description 2
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 claims description 2
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 claims description 2
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 claims description 2
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- OYIKARCXOQLFHF-UHFFFAOYSA-N isoxaflutole Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OYIKARCXOQLFHF-UHFFFAOYSA-N 0.000 claims description 2
- 229940088649 isoxaflutole Drugs 0.000 claims description 2
- 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 2
- 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 2
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 claims description 2
- 239000005583 Metribuzin Substances 0.000 claims 1
- 239000005586 Nicosulfuron Substances 0.000 claims 1
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 claims 1
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract description 13
- 150000003839 salts Chemical class 0.000 abstract description 6
- 239000000243 solution Substances 0.000 description 419
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 207
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 204
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 182
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 154
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 122
- 238000006243 chemical reaction Methods 0.000 description 120
- 239000002904 solvent Substances 0.000 description 116
- 238000005292 vacuum distillation Methods 0.000 description 113
- 238000002360 preparation method Methods 0.000 description 110
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 108
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 107
- 239000011541 reaction mixture Substances 0.000 description 104
- 239000012044 organic layer Substances 0.000 description 101
- 239000011780 sodium chloride Substances 0.000 description 101
- 238000005160 1H NMR spectroscopy Methods 0.000 description 82
- 238000000605 extraction Methods 0.000 description 79
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 79
- 239000003153 chemical reaction reagent Substances 0.000 description 76
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 73
- 238000010898 silica gel chromatography Methods 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 50
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 50
- 238000001816 cooling Methods 0.000 description 45
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 40
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 239000013078 crystal Substances 0.000 description 31
- 239000003480 eluent Substances 0.000 description 31
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 28
- 241000196324 Embryophyta Species 0.000 description 28
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 26
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 26
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 25
- 235000017557 sodium bicarbonate Nutrition 0.000 description 25
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 25
- 239000000126 substance Substances 0.000 description 22
- 229910000027 potassium carbonate Inorganic materials 0.000 description 20
- 235000011181 potassium carbonates Nutrition 0.000 description 20
- 239000000843 powder Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000376 reactant Substances 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 231100000674 Phytotoxicity Toxicity 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 240000008042 Zea mays Species 0.000 description 12
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 12
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 240000006995 Abutilon theophrasti Species 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- 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
- 240000006394 Sorghum bicolor Species 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 7
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 235000009973 maize Nutrition 0.000 description 7
- 239000012265 solid product Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 239000004563 wettable powder Substances 0.000 description 7
- 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
- 240000006162 Chenopodium quinoa Species 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-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
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 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
- 235000009344 Chenopodium album Nutrition 0.000 description 5
- 240000006122 Chenopodium album Species 0.000 description 5
- 235000010469 Glycine max Nutrition 0.000 description 5
- 244000068988 Glycine max Species 0.000 description 5
- 240000003461 Setaria viridis Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- JCPGTXJOEHCHIO-UHFFFAOYSA-N 3-benzylsulfanyl-5,5-dimethyl-4h-1,2-oxazole Chemical compound O1C(C)(C)CC(SCC=2C=CC=CC=2)=N1 JCPGTXJOEHCHIO-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
- 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
- GUMRBYBFTLXIKZ-UHFFFAOYSA-N 5-bromo-6-(trifluoromethyl)-1h-pyrimidin-4-one Chemical compound OC1=NC=NC(C(F)(F)F)=C1Br GUMRBYBFTLXIKZ-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
- 241001290610 Abildgaardia Species 0.000 description 4
- 241001621841 Alopecurus myosuroides Species 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
- 244000108484 Cyperus difformis Species 0.000 description 4
- 235000005853 Cyperus esculentus Nutrition 0.000 description 4
- 244000285790 Cyperus iria Species 0.000 description 4
- 240000003176 Digitaria ciliaris Species 0.000 description 4
- 235000017898 Digitaria ciliaris Nutrition 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
- 240000005979 Hordeum vulgare Species 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- 235000003403 Limnocharis flava Nutrition 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 241000533293 Sesbania emerus Species 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 244000269888 azena Species 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 4
- 206010020488 hydrocele Diseases 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- PRMZWQLUQGMHIP-UHFFFAOYSA-N (3,5-dichloro-1-ethylpyrazol-4-yl)methanol Chemical compound CCN1N=C(Cl)C(CO)=C1Cl PRMZWQLUQGMHIP-UHFFFAOYSA-N 0.000 description 3
- PPBIJPOXGAPZLI-UHFFFAOYSA-N 1-tert-butyl-4-(chloromethyl)-5-methoxy-3-(trifluoromethyl)pyrazole Chemical compound COC1=C(CCl)C(C(F)(F)F)=NN1C(C)(C)C PPBIJPOXGAPZLI-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
- 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 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
- 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
- QFSVUWWSVZOKGT-UHFFFAOYSA-N 3-[[3-chloro-1-(difluoromethyl)-5-(trifluoromethyl)pyrazol-4-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound O1C(C)(C)CC(S(=O)(=O)CC2=C(N(C(F)F)N=C2Cl)C(F)(F)F)=N1 QFSVUWWSVZOKGT-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
- ZGTGWICGSZWWDJ-UHFFFAOYSA-N 3-[[3-methoxy-1-methyl-5-(trifluoromethyl)pyrazol-4-yl]methylsulfanyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound COC1=NN(C)C(C(F)(F)F)=C1CSC1=NOC(C)(C)C1 ZGTGWICGSZWWDJ-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
- RMOPLYDGQNYJNA-UHFFFAOYSA-N 3-[[5-ethylsulfanyl-1-phenyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfanyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound FC(F)(F)C1=NN(C=2C=CC=CC=2)C(SCC)=C1CSC1=NOC(C)(C)C1 RMOPLYDGQNYJNA-UHFFFAOYSA-N 0.000 description 3
- VYDNLKDEWKLVAN-UHFFFAOYSA-N 3-[[5-methoxy-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfanyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound FC(F)(F)C1=NN(C)C(OC)=C1CSC1=NOC(C)(C)C1 VYDNLKDEWKLVAN-UHFFFAOYSA-N 0.000 description 3
- USZCFLDZOXNCSR-UHFFFAOYSA-N 3-methoxy-1-methyl-5-(trifluoromethyl)pyrazole Chemical compound COC=1C=C(C(F)(F)F)N(C)N=1 USZCFLDZOXNCSR-UHFFFAOYSA-N 0.000 description 3
- PWWVHBMXDFWYMJ-UHFFFAOYSA-N 4-(bromomethyl)-3,5-dichloro-1-ethylpyrazole Chemical compound CCN1N=C(Cl)C(CBr)=C1Cl PWWVHBMXDFWYMJ-UHFFFAOYSA-N 0.000 description 3
- UBCASBANOXIWEA-UHFFFAOYSA-N 4-(bromomethyl)-5-fluoro-1-phenyl-3-(trifluoromethyl)pyrazole Chemical compound FC1=C(CBr)C(C(F)(F)F)=NN1C1=CC=CC=C1 UBCASBANOXIWEA-UHFFFAOYSA-N 0.000 description 3
- OMGCDROEKODBDC-UHFFFAOYSA-N 4-(bromomethyl)-5-methyl-3-(trifluoromethyl)-1,2-oxazole Chemical compound CC=1ON=C(C(F)(F)F)C=1CBr OMGCDROEKODBDC-UHFFFAOYSA-N 0.000 description 3
- KPLPYYZPPCOADF-UHFFFAOYSA-N 4-[(5,5-dimethyl-4h-1,2-oxazol-3-yl)sulfanylmethyl]-2-methyl-3-(trifluoromethyl)-1h-pyrazol-5-one Chemical compound CN1N=C(O)C(CSC=2CC(C)(C)ON=2)=C1C(F)(F)F KPLPYYZPPCOADF-UHFFFAOYSA-N 0.000 description 3
- DXMBMVBXPYJHOM-UHFFFAOYSA-N 4-ethoxy-6-(trifluoromethyl)pyrimidine-5-carbaldehyde Chemical compound CCOC1=NC=NC(C(F)(F)F)=C1C=O DXMBMVBXPYJHOM-UHFFFAOYSA-N 0.000 description 3
- VEIPKLIIXBPVCG-UHFFFAOYSA-N 5-(difluoromethyl)-2-methyl-1h-pyrazol-3-one Chemical compound CN1NC(C(F)F)=CC1=O VEIPKLIIXBPVCG-UHFFFAOYSA-N 0.000 description 3
- IVCWZRVBVMKQNS-UHFFFAOYSA-N 5-bromo-4-ethoxy-6-(trifluoromethyl)pyrimidine Chemical compound CCOC1=NC=NC(C(F)(F)F)=C1Br IVCWZRVBVMKQNS-UHFFFAOYSA-N 0.000 description 3
- NMYPMEAFQUDCSC-UHFFFAOYSA-N 5-chloro-3-(difluoromethyl)-1-methylpyrazole-4-carbaldehyde Chemical compound CN1N=C(C(F)F)C(C=O)=C1Cl NMYPMEAFQUDCSC-UHFFFAOYSA-N 0.000 description 3
- 244000036975 Ambrosia artemisiifolia Species 0.000 description 3
- 235000003133 Ambrosia artemisiifolia Nutrition 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- 241000282461 Canis lupus Species 0.000 description 3
- 235000000509 Chenopodium ambrosioides Nutrition 0.000 description 3
- 235000005490 Chenopodium botrys Nutrition 0.000 description 3
- 244000098897 Chenopodium botrys Species 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 241000219146 Gossypium Species 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 3
- 240000001439 Opuntia Species 0.000 description 3
- 235000013389 Opuntia humifusa var. humifusa Nutrition 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- 240000006410 Sida spinosa Species 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 240000002439 Sorghum halepense Species 0.000 description 3
- 235000021536 Sugar beet Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000243774 Trichinella Species 0.000 description 3
- 241001148683 Zostera marina Species 0.000 description 3
- RGIWQEWTVQLNFW-UHFFFAOYSA-N [1-tert-butyl-5-chloro-3-(trifluoromethyl)pyrazol-4-yl]methanol Chemical compound CC(C)(C)N1N=C(C(F)(F)F)C(CO)=C1Cl RGIWQEWTVQLNFW-UHFFFAOYSA-N 0.000 description 3
- HOHRENOBPUZLEM-UHFFFAOYSA-N [4-ethoxy-6-(trifluoromethyl)pyrimidin-5-yl]methanol Chemical compound CCOC1=NC=NC(C(F)(F)F)=C1CO HOHRENOBPUZLEM-UHFFFAOYSA-N 0.000 description 3
- NWMIWQASEUTFJK-UHFFFAOYSA-N [5-chloro-1-phenyl-3-(trifluoromethyl)pyrazol-4-yl]methanol Chemical compound N1=C(C(F)(F)F)C(CO)=C(Cl)N1C1=CC=CC=C1 NWMIWQASEUTFJK-UHFFFAOYSA-N 0.000 description 3
- OWJSUNGDWUHQDU-UHFFFAOYSA-N [5-chloro-3-(difluoromethyl)-1-methylpyrazol-4-yl]methanol Chemical compound CN1N=C(C(F)F)C(CO)=C1Cl OWJSUNGDWUHQDU-UHFFFAOYSA-N 0.000 description 3
- WIABTIBXPLJUKQ-UHFFFAOYSA-N [5-fluoro-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methanol Chemical compound CN1N=C(C(F)(F)F)C(CO)=C1F WIABTIBXPLJUKQ-UHFFFAOYSA-N 0.000 description 3
- NSVBKJADMFIJKW-UHFFFAOYSA-N [5-fluoro-1-phenyl-3-(trifluoromethyl)pyrazol-4-yl]methanol Chemical compound N1=C(C(F)(F)F)C(CO)=C(F)N1C1=CC=CC=C1 NSVBKJADMFIJKW-UHFFFAOYSA-N 0.000 description 3
- JHZMZOMPBAVNRM-UHFFFAOYSA-N [5-methyl-3-(trifluoromethyl)-1,2-oxazol-4-yl]methanol Chemical compound CC=1ON=C(C(F)(F)F)C=1CO JHZMZOMPBAVNRM-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000009194 climbing Effects 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- KACZQOKEFKFNDB-UHFFFAOYSA-N ethyl 1h-pyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NNC=1 KACZQOKEFKFNDB-UHFFFAOYSA-N 0.000 description 3
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 229940118019 malondialdehyde Drugs 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- IHYNKGRWCDKNEG-UHFFFAOYSA-N n-(4-bromophenyl)-2,6-dihydroxybenzamide Chemical compound OC1=CC=CC(O)=C1C(=O)NC1=CC=C(Br)C=C1 IHYNKGRWCDKNEG-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 3
- XODPQKCXGFBFHX-UHFFFAOYSA-M sodium;hydrogen sulfite;hydrate Chemical compound O.[Na+].OS([O-])=O XODPQKCXGFBFHX-UHFFFAOYSA-M 0.000 description 3
- BGKJXQIITJQALO-UHFFFAOYSA-N (2-chloro-4-methylpyridin-3-yl)methanol Chemical compound CC1=CC=NC(Cl)=C1CO BGKJXQIITJQALO-UHFFFAOYSA-N 0.000 description 2
- FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 description 2
- BRGAFNIVBLUDTK-UHFFFAOYSA-N 1-[2,5-dichloro-4-(chloromethyl)thiophen-3-yl]ethanone Chemical compound CC(=O)C1=C(Cl)SC(Cl)=C1CCl BRGAFNIVBLUDTK-UHFFFAOYSA-N 0.000 description 2
- IDPCDFLMTBSYSH-UHFFFAOYSA-N 1-[4-[(5,5-dimethyl-4h-1,2-oxazol-3-yl)sulfanylmethyl]-2,5-dimethylthiophen-3-yl]-n-methoxyethanimine Chemical compound CON=C(C)C1=C(C)SC(C)=C1CSC1=NOC(C)(C)C1 IDPCDFLMTBSYSH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JFRPJKPEZUJXMR-UHFFFAOYSA-N 2,2,2-trifluoro-n-hydroxyethanimidoyl bromide Chemical compound ON=C(Br)C(F)(F)F JFRPJKPEZUJXMR-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OVXHLEYZFKRACG-UHFFFAOYSA-N 3-[(3,5-dichloro-1-ethylpyrazol-4-yl)methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CCN1N=C(Cl)C(CS(=O)(=O)C=2CC(C)(C)ON=2)=C1Cl OVXHLEYZFKRACG-UHFFFAOYSA-N 0.000 description 2
- SYJDLAUWJAOAPI-UHFFFAOYSA-N 3-[(5,5-dimethyl-4h-1,2-oxazol-3-yl)sulfanylmethyl]-2-(trifluoromethyl)-6,7-dihydro-5h-pyrazolo[5,1-b][1,3]oxazine Chemical compound O1C(C)(C)CC(SCC=2C(=NN3CCCOC3=2)C(F)(F)F)=N1 SYJDLAUWJAOAPI-UHFFFAOYSA-N 0.000 description 2
- VUCMLQKDJMEHBC-UHFFFAOYSA-N 3-[(5-chloro-3-methyl-1,2-thiazol-4-yl)methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CC1=NSC(Cl)=C1CS(=O)(=O)C1=NOC(C)(C)C1 VUCMLQKDJMEHBC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WHNIEOVHFTVTFA-UHFFFAOYSA-N 3-[[3-chloro-5-(trifluoromethyl)-1h-pyrazol-4-yl]methylsulfanyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound O1C(C)(C)CC(SCC=2C(=NNC=2Cl)C(F)(F)F)=N1 WHNIEOVHFTVTFA-UHFFFAOYSA-N 0.000 description 2
- RVQXKGBYCCLROP-UHFFFAOYSA-N 3-[[3-ethoxy-1-methyl-5-(trifluoromethyl)pyrazol-4-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CCOC1=NN(C)C(C(F)(F)F)=C1CS(=O)(=O)C1=NOC(C)(C)C1 RVQXKGBYCCLROP-UHFFFAOYSA-N 0.000 description 2
- NBOGWWPYWPIRQV-UHFFFAOYSA-N 3-[[4-methoxy-6-(trifluoromethyl)pyrimidin-5-yl]methylsulfanyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound COC1=NC=NC(C(F)(F)F)=C1CSC1=NOC(C)(C)C1 NBOGWWPYWPIRQV-UHFFFAOYSA-N 0.000 description 2
- XEXMQEPKEFWXPD-UHFFFAOYSA-N 3-[[4-methoxy-6-(trifluoromethyl)pyrimidin-5-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound COC1=NC=NC(C(F)(F)F)=C1CS(=O)(=O)C1=NOC(C)(C)C1 XEXMQEPKEFWXPD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VKQFYIYGCPBPBL-UHFFFAOYSA-N 3-[[5-(difluoromethoxy)-1-ethyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CCN1N=C(C(F)(F)F)C(CS(=O)(=O)C=2CC(C)(C)ON=2)=C1OC(F)F VKQFYIYGCPBPBL-UHFFFAOYSA-N 0.000 description 2
- CASLETQIYIQFTQ-UHFFFAOYSA-N 3-[[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CN1N=C(C(F)(F)F)C(CS(=O)(=O)C=2CC(C)(C)ON=2)=C1OC(F)F CASLETQIYIQFTQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZASFSMRVMLRVNU-UHFFFAOYSA-N 3-[[5-chloro-1-(difluoromethyl)-3-(trifluoromethyl)pyrazol-4-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound O1C(C)(C)CC(S(=O)(=O)CC=2C(=NN(C=2Cl)C(F)F)C(F)(F)F)=N1 ZASFSMRVMLRVNU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XOZBOQPLLKVKFW-UHFFFAOYSA-N 3-[[5-chloro-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CN1N=C(C(F)(F)F)C(CS(=O)(=O)C=2CC(C)(C)ON=2)=C1Cl XOZBOQPLLKVKFW-UHFFFAOYSA-N 0.000 description 2
- GOJZKELWLXCABR-UHFFFAOYSA-N 3-[[5-chloro-1-phenyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound O1C(C)(C)CC(S(=O)(=O)CC=2C(=NN(C=2Cl)C=2C=CC=CC=2)C(F)(F)F)=N1 GOJZKELWLXCABR-UHFFFAOYSA-N 0.000 description 2
- KJJALSHMPGFGEV-UHFFFAOYSA-N 3-[[5-chloro-3-(difluoromethyl)-1-methylpyrazol-4-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CN1N=C(C(F)F)C(CS(=O)(=O)C=2CC(C)(C)ON=2)=C1Cl KJJALSHMPGFGEV-UHFFFAOYSA-N 0.000 description 2
- NLLIJHFMDAPPGH-UHFFFAOYSA-N 3-[[5-cyclopentyloxy-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound C1CCCC1OC=1N(C)N=C(C(F)(F)F)C=1CS(=O)(=O)C1=NOC(C)(C)C1 NLLIJHFMDAPPGH-UHFFFAOYSA-N 0.000 description 2
- VLCBJLHRHPKSOT-UHFFFAOYSA-N 3-[[5-ethylsulfonyl-1-phenyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound FC(F)(F)C1=NN(C=2C=CC=CC=2)C(S(=O)(=O)CC)=C1CS(=O)(=O)C1=NOC(C)(C)C1 VLCBJLHRHPKSOT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BXTZYFMKNPYKEG-UHFFFAOYSA-N 3-[[5-fluoro-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=2F)C=2C=CC=CC=2)C(F)(F)F)=N1 BXTZYFMKNPYKEG-UHFFFAOYSA-N 0.000 description 2
- UVFJJUHGXHAETP-UHFFFAOYSA-N 3-[[5-methoxy-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound FC(F)(F)C1=NN(C)C(OC)=C1CS(=O)(=O)C1=NOC(C)(C)C1 UVFJJUHGXHAETP-UHFFFAOYSA-N 0.000 description 2
- WIHABELRBPWGPB-UHFFFAOYSA-N 3-bromo-2-(bromomethyl)-1-benzofuran Chemical compound C1=CC=C2C(Br)=C(CBr)OC2=C1 WIHABELRBPWGPB-UHFFFAOYSA-N 0.000 description 2
- CAJGZJFXRJOICD-UHFFFAOYSA-N 3-chloro-5-ethyl-5-methyl-4h-1,2-oxazole Chemical compound CCC1(C)CC(Cl)=NO1 CAJGZJFXRJOICD-UHFFFAOYSA-N 0.000 description 2
- WNGVLRQBPHWCQF-UHFFFAOYSA-N 3-ethyl-5,5-dimethyl-4h-1,2-thiazole Chemical compound CCC1=NSC(C)(C)C1 WNGVLRQBPHWCQF-UHFFFAOYSA-N 0.000 description 2
- UAXQPXGYYNUYAL-UHFFFAOYSA-N 4-(bromomethyl)-5-chloro-1-phenyl-3-(trifluoromethyl)pyrazole Chemical compound ClC1=C(CBr)C(C(F)(F)F)=NN1C1=CC=CC=C1 UAXQPXGYYNUYAL-UHFFFAOYSA-N 0.000 description 2
- YXLRFHPPZQYLLL-UHFFFAOYSA-N 4-(bromomethyl)-5-chloro-3-(difluoromethyl)-1-methylpyrazole Chemical compound CN1N=C(C(F)F)C(CBr)=C1Cl YXLRFHPPZQYLLL-UHFFFAOYSA-N 0.000 description 2
- BTOKWXQACBYLHM-UHFFFAOYSA-N 4-(bromomethyl)-5-fluoro-1-methyl-3-(trifluoromethyl)pyrazole Chemical compound CN1N=C(C(F)(F)F)C(CBr)=C1F BTOKWXQACBYLHM-UHFFFAOYSA-N 0.000 description 2
- RENBNIBODBOWAA-UHFFFAOYSA-N 4-(chloromethyl)-3-methoxy-1-methyl-5-(trifluoromethyl)pyrazole Chemical compound COC1=NN(C)C(C(F)(F)F)=C1CCl RENBNIBODBOWAA-UHFFFAOYSA-N 0.000 description 2
- LMRJHNFECNKDKH-UHFFFAOYSA-N 4-(trifluoromethyl)nicotinic acid Chemical compound OC(=O)C1=CN=CC=C1C(F)(F)F LMRJHNFECNKDKH-UHFFFAOYSA-N 0.000 description 2
- QVLBUKMEMCNODZ-UHFFFAOYSA-N 4-[(5,5-dimethyl-4h-1,2-oxazol-3-yl)sulfanylmethyl]-2-methyl-5-(trifluoromethyl)pyrazole-3-carbonitrile Chemical compound CN1N=C(C(F)(F)F)C(CSC=2CC(C)(C)ON=2)=C1C#N QVLBUKMEMCNODZ-UHFFFAOYSA-N 0.000 description 2
- ZLSIWSQQUVADRF-UHFFFAOYSA-N 4-[(5,5-dimethyl-4h-1,2-oxazol-3-yl)sulfanylmethyl]-n,n-dimethyl-2-phenyl-5-(trifluoromethyl)pyrazol-3-amine Chemical compound FC(F)(F)C1=NN(C=2C=CC=CC=2)C(N(C)C)=C1CSC1=NOC(C)(C)C1 ZLSIWSQQUVADRF-UHFFFAOYSA-N 0.000 description 2
- LUCWGIHJQCCLNM-UHFFFAOYSA-N 4-[(5,5-dimethyl-4h-1,2-oxazol-3-yl)sulfonylmethyl]-2-methyl-5-(trifluoromethyl)pyrazole-3-carbonitrile Chemical compound CN1N=C(C(F)(F)F)C(CS(=O)(=O)C=2CC(C)(C)ON=2)=C1C#N LUCWGIHJQCCLNM-UHFFFAOYSA-N 0.000 description 2
- GFTFFFSXUCAXAN-UHFFFAOYSA-N 4-[(5,5-dimethyl-4h-1,2-oxazol-3-yl)sulfonylmethyl]-5-methyl-3-(trifluoromethyl)-1,2-oxazole Chemical compound O1N=C(C(F)(F)F)C(CS(=O)(=O)C=2CC(C)(C)ON=2)=C1C GFTFFFSXUCAXAN-UHFFFAOYSA-N 0.000 description 2
- FXARLIBGHZIJMB-UHFFFAOYSA-N 4-[(5,5-dimethyl-4h-1,2-oxazol-3-yl)sulfonylmethyl]-n,n-dimethyl-2-phenyl-5-(trifluoromethyl)pyrazol-3-amine Chemical compound FC(F)(F)C1=NN(C=2C=CC=CC=2)C(N(C)C)=C1CS(=O)(=O)C1=NOC(C)(C)C1 FXARLIBGHZIJMB-UHFFFAOYSA-N 0.000 description 2
- QWQDDDUJMPUIQS-UHFFFAOYSA-N 5,5-dimethyl-3-[[4-(trifluoromethyl)pyridin-3-yl]methylsulfanyl]-4h-1,2-oxazole Chemical compound O1C(C)(C)CC(SCC=2C(=CC=NC=2)C(F)(F)F)=N1 QWQDDDUJMPUIQS-UHFFFAOYSA-N 0.000 description 2
- YYHBMSHQXDQBFA-UHFFFAOYSA-N 5,5-dimethyl-3-[[4-(trifluoromethyl)pyridin-3-yl]methylsulfonyl]-4h-1,2-oxazole Chemical compound O1C(C)(C)CC(S(=O)(=O)CC=2C(=CC=NC=2)C(F)(F)F)=N1 YYHBMSHQXDQBFA-UHFFFAOYSA-N 0.000 description 2
- SSCJAEUDVGKGHG-UHFFFAOYSA-N 5-(chloromethyl)-4-methoxy-6-(trifluoromethyl)pyrimidine Chemical compound COC1=NC=NC(C(F)(F)F)=C1CCl SSCJAEUDVGKGHG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JQZOQTOCCSXHPI-UHFFFAOYSA-N 5-chloro-4-(chloromethyl)-3-methyl-1,2-thiazole Chemical compound CC1=NSC(Cl)=C1CCl JQZOQTOCCSXHPI-UHFFFAOYSA-N 0.000 description 2
- OJKIPJVJFWPIJP-UHFFFAOYSA-N 5-fluoro-1-methyl-3-(trifluoromethyl)pyrazole-4-carbaldehyde Chemical compound CN1N=C(C(F)(F)F)C(C=O)=C1F OJKIPJVJFWPIJP-UHFFFAOYSA-N 0.000 description 2
- ZFJUPYFIENDXBI-UHFFFAOYSA-N 5-fluoro-1-phenyl-3-(trifluoromethyl)pyrazole-4-carbaldehyde Chemical compound FC1=C(C=O)C(C(F)(F)F)=NN1C1=CC=CC=C1 ZFJUPYFIENDXBI-UHFFFAOYSA-N 0.000 description 2
- 244000001632 Acorus gramineus Species 0.000 description 2
- 235000004135 Amaranthus viridis Nutrition 0.000 description 2
- 244000055702 Amaranthus viridis Species 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000209761 Avena Species 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- 241000209764 Avena fatua Species 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 241000103725 Cyperus esculentus var. esculentus Species 0.000 description 2
- 241000817048 Cyperus microiria Species 0.000 description 2
- 240000001505 Cyperus odoratus Species 0.000 description 2
- 244000075634 Cyperus rotundus Species 0.000 description 2
- 206010011878 Deafness Diseases 0.000 description 2
- 241000192043 Echinochloa Species 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 241000192040 Echinochloa phyllopogon Species 0.000 description 2
- 241000759118 Eleocharis kuroguwai Species 0.000 description 2
- 235000014716 Eleusine indica Nutrition 0.000 description 2
- 241000508725 Elymus repens Species 0.000 description 2
- 244000192024 Euphorbia helioscopia Species 0.000 description 2
- 235000012043 Euphorbia helioscopia Nutrition 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 240000007218 Ipomoea hederacea Species 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 244000157344 Kyllinga brevifolia Species 0.000 description 2
- 240000000178 Monochoria vaginalis Species 0.000 description 2
- 235000015225 Panicum colonum Nutrition 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 244000292693 Poa annua Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 241000205407 Polygonum Species 0.000 description 2
- 244000292697 Polygonum aviculare Species 0.000 description 2
- 235000006386 Polygonum aviculare Nutrition 0.000 description 2
- 244000234609 Portulaca oleracea Species 0.000 description 2
- 235000001855 Portulaca oleracea Nutrition 0.000 description 2
- 244000085269 Scirpus juncoides Species 0.000 description 2
- 235000002248 Setaria viridis Nutrition 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 235000002594 Solanum nigrum Nutrition 0.000 description 2
- 244000061457 Solanum nigrum Species 0.000 description 2
- 240000006694 Stellaria media Species 0.000 description 2
- 241001083492 Trapa Species 0.000 description 2
- 206010044608 Trichiniasis Diseases 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- UUSGYEBVVABINX-UHFFFAOYSA-N [1-tert-butyl-5-chloro-3-(trifluoromethyl)pyrazol-4-yl]methanethiol Chemical compound CC(C)(C)N1N=C(C(F)(F)F)C(CS)=C1Cl UUSGYEBVVABINX-UHFFFAOYSA-N 0.000 description 2
- WQRWBLLHQHAGBM-UHFFFAOYSA-N [4-(trifluoromethyl)pyridin-3-yl]methanol Chemical compound OCC1=CN=CC=C1C(F)(F)F WQRWBLLHQHAGBM-UHFFFAOYSA-N 0.000 description 2
- ILIHQFSZGRGBEN-UHFFFAOYSA-N [4-methoxy-6-(trifluoromethyl)pyrimidin-5-yl]methanol Chemical compound COC1=NC=NC(C(F)(F)F)=C1CO ILIHQFSZGRGBEN-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 235000021186 dishes Nutrition 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- XDGRKQJBBYAGQA-UHFFFAOYSA-N ethyl 1-ethylpyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NN(CC)C=1 XDGRKQJBBYAGQA-UHFFFAOYSA-N 0.000 description 2
- KKUDZDKGPZZJSR-UHFFFAOYSA-N ethyl 3,5-dichloro-1-ethylpyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C(Cl)=NN(CC)C=1Cl KKUDZDKGPZZJSR-UHFFFAOYSA-N 0.000 description 2
- OCJKUQIPRNZDTK-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)C(F)(F)F OCJKUQIPRNZDTK-UHFFFAOYSA-N 0.000 description 2
- BDBPOYLTYVIRRW-UHFFFAOYSA-N ethyl 5-methyl-3-(trifluoromethyl)-1,2-oxazole-4-carboxylate Chemical compound CCOC(=O)C1=C(C)ON=C1C(F)(F)F BDBPOYLTYVIRRW-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 230000009036 growth inhibition Effects 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- RFUABQNZKSSKRX-UHFFFAOYSA-N methyl 4-(trifluoromethyl)pyridine-3-carboxylate Chemical compound COC(=O)C1=CN=CC=C1C(F)(F)F RFUABQNZKSSKRX-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- AGXIAHLLNDREAE-UHFFFAOYSA-N n-(2,2,2-trifluoroethylidene)hydroxylamine Chemical compound ON=CC(F)(F)F AGXIAHLLNDREAE-UHFFFAOYSA-N 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 231100000208 phytotoxic Toxicity 0.000 description 2
- 230000000885 phytotoxic effect Effects 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- 235000003270 potassium fluoride Nutrition 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- WRVHPSSSTBDGRK-UHFFFAOYSA-N sodium;sulfane;hydrate Chemical compound O.[Na].S WRVHPSSSTBDGRK-UHFFFAOYSA-N 0.000 description 2
- ZNKXTIAQRUWLRL-UHFFFAOYSA-M sodium;sulfane;hydroxide Chemical compound O.[Na+].[SH-] ZNKXTIAQRUWLRL-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 244000082735 tidal marsh flat sedge Species 0.000 description 2
- 208000003982 trichinellosis Diseases 0.000 description 2
- 201000007588 trichinosis Diseases 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- GYFDNIRENHZKGR-UHFFFAOYSA-N 1-(2,5-dichlorothiophen-3-yl)ethanone Chemical compound CC(=O)C=1C=C(Cl)SC=1Cl GYFDNIRENHZKGR-UHFFFAOYSA-N 0.000 description 1
- WVRXNIBQZAKZTE-UHFFFAOYSA-N 1-methylidene-2h-naphthalene Chemical compound C1=CC=C2C(=C)CC=CC2=C1 WVRXNIBQZAKZTE-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- QEHXHKNBIGEWIH-UHFFFAOYSA-N 2-methyl-3-(trifluoromethyl)-1h-pyrazol-5-one Chemical compound CN1NC(=O)C=C1C(F)(F)F QEHXHKNBIGEWIH-UHFFFAOYSA-N 0.000 description 1
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- LNJMHEJAYSYZKK-UHFFFAOYSA-N 2-methylpyrimidine Chemical class CC1=NC=CC=N1 LNJMHEJAYSYZKK-UHFFFAOYSA-N 0.000 description 1
- FJKSTRHPBRJXQH-UHFFFAOYSA-N 3,5,5-trimethyl-4h-1,2-thiazole Chemical compound CC1=NSC(C)(C)C1 FJKSTRHPBRJXQH-UHFFFAOYSA-N 0.000 description 1
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical class COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
- ZHXNIELBUAZCFU-UHFFFAOYSA-N 3-[(2,6-difluorophenyl)methylsulfanyl]-5-ethyl-5-methyl-4h-1,2-oxazole Chemical compound O1C(CC)(C)CC(SCC=2C(=CC=CC=2F)F)=N1 ZHXNIELBUAZCFU-UHFFFAOYSA-N 0.000 description 1
- FUXNQLGMPQPOFB-UHFFFAOYSA-N 3-[(2,6-difluorophenyl)methylsulfonyl]-5-ethyl-5-methyl-4h-1,2-oxazole Chemical compound O1C(CC)(C)CC(S(=O)(=O)CC=2C(=CC=CC=2F)F)=N1 FUXNQLGMPQPOFB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DSDDVDDXHQRDTF-UHFFFAOYSA-N 3-[[5-(2-chlorophenoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfonyl]-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=1CS(=O)(=O)C1=NOC(C)(C)C1 DSDDVDDXHQRDTF-UHFFFAOYSA-N 0.000 description 1
- ARJPLYZBOHQOCK-UHFFFAOYSA-N 3-[[5-(difluoromethoxy)-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)=C1OC(F)F ARJPLYZBOHQOCK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OEGMISNFEAVBHA-UHFFFAOYSA-N 3-bromo-2-methyl-1-benzofuran Chemical compound C1=CC=C2C(Br)=C(C)OC2=C1 OEGMISNFEAVBHA-UHFFFAOYSA-N 0.000 description 1
- AWCSZMCGZWMNBD-UHFFFAOYSA-N 3-ethyl-5,5-dimethyl-4h-1,2-oxazole Chemical compound CCC1=NOC(C)(C)C1 AWCSZMCGZWMNBD-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical group C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 description 1
- ORQGJPFVTDVXAK-UHFFFAOYSA-N 4-(bromomethyl)-5-chloro-1-methyl-3-(trifluoromethyl)pyrazole Chemical compound CN1N=C(C(F)(F)F)C(CBr)=C1Cl ORQGJPFVTDVXAK-UHFFFAOYSA-N 0.000 description 1
- NAQCBYNVOXNMLO-UHFFFAOYSA-N 4-(chloromethyl)-3-methyl-1,2-thiazole Chemical compound CC1=NSC=C1CCl NAQCBYNVOXNMLO-UHFFFAOYSA-N 0.000 description 1
- RBLKJQVDAMPTPJ-UHFFFAOYSA-N 4-[(5,5-dimethyl-4h-1,2-oxazol-3-yl)sulfanylmethyl]-5-methyl-3-(trifluoromethyl)-1,2-oxazole Chemical compound O1N=C(C(F)(F)F)C(CSC=2CC(C)(C)ON=2)=C1C RBLKJQVDAMPTPJ-UHFFFAOYSA-N 0.000 description 1
- NLGGHPSGMYCFPZ-UHFFFAOYSA-N 4-chloro-3-(difluoromethyl)-1-methylpyrazole Chemical compound CN1C=C(Cl)C(C(F)F)=N1 NLGGHPSGMYCFPZ-UHFFFAOYSA-N 0.000 description 1
- KCYFPOLHJZXCEE-UHFFFAOYSA-N 4-methoxy-6-(trifluoromethyl)pyrimidine Chemical compound COC1=CC(C(F)(F)F)=NC=N1 KCYFPOLHJZXCEE-UHFFFAOYSA-N 0.000 description 1
- DIYSFZUJSGOINT-UHFFFAOYSA-N 5,5-dimethyl-4h-1,2-oxazole Chemical class CC1(C)CC=NO1 DIYSFZUJSGOINT-UHFFFAOYSA-N 0.000 description 1
- OQVFVBPQAXFVBF-UHFFFAOYSA-N 5-(bromomethyl)-4-ethoxy-6-(trifluoromethyl)pyrimidine Chemical compound CCOC1=NC=NC(C(F)(F)F)=C1CBr OQVFVBPQAXFVBF-UHFFFAOYSA-N 0.000 description 1
- FJJAWLIAGKXVBI-UHFFFAOYSA-N 5-chloro-1-(difluoromethyl)-3-(trifluoromethyl)pyrazole Chemical compound ClC1=CC(=NN1C(F)F)C(F)(F)F FJJAWLIAGKXVBI-UHFFFAOYSA-N 0.000 description 1
- AXVYNMMTYBGOFD-UHFFFAOYSA-N 5-chloro-1-methyl-3-(trifluoromethyl)pyrazole Chemical compound CN1N=C(C(F)(F)F)C=C1Cl AXVYNMMTYBGOFD-UHFFFAOYSA-N 0.000 description 1
- PZOZNOVIRZSNHJ-UHFFFAOYSA-N 5-chloro-1-methyl-3-(trifluoromethyl)pyrazole-4-carbaldehyde Chemical compound CN1N=C(C(F)(F)F)C(C=O)=C1Cl PZOZNOVIRZSNHJ-UHFFFAOYSA-N 0.000 description 1
- LEUUCQCWCLNKMN-UHFFFAOYSA-N 5-chloro-3-(difluoromethyl)-1-methylpyrazole Chemical compound CN1N=C(C(F)F)C=C1Cl LEUUCQCWCLNKMN-UHFFFAOYSA-N 0.000 description 1
- GXEHEYRVMPXMAW-UHFFFAOYSA-N 5-fluoro-1-methyl-3-(trifluoromethyl)pyrazole Chemical compound CN1N=C(C(F)(F)F)C=C1F GXEHEYRVMPXMAW-UHFFFAOYSA-N 0.000 description 1
- LVOYSBZJJWPUBD-UHFFFAOYSA-N 6-(trifluoromethyl)-1h-pyrimidin-4-one Chemical compound OC1=CC(C(F)(F)F)=NC=N1 LVOYSBZJJWPUBD-UHFFFAOYSA-N 0.000 description 1
- 240000000254 Agrostemma githago Species 0.000 description 1
- 235000009899 Agrostemma githago Nutrition 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 244000237956 Amaranthus retroflexus Species 0.000 description 1
- 241000143476 Bidens Species 0.000 description 1
- 241000498899 Bidens frondosa Species 0.000 description 1
- 235000010662 Bidens pilosa Nutrition 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 244000024671 Brassica kaber Species 0.000 description 1
- 235000014750 Brassica kaber Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FDKQKQFREDULLD-UHFFFAOYSA-N CC1(CON=C1SCC2=C(N(N=C2C(F)(F)F)C)F)C Chemical compound CC1(CON=C1SCC2=C(N(N=C2C(F)(F)F)C)F)C FDKQKQFREDULLD-UHFFFAOYSA-N 0.000 description 1
- VKRUXWAITIEXFR-UHFFFAOYSA-N CN1N=C(C(F)(F)F)C(CSC=2CC(C)(C)ON=2)=C1O Chemical compound CN1N=C(C(F)(F)F)C(CSC=2CC(C)(C)ON=2)=C1O VKRUXWAITIEXFR-UHFFFAOYSA-N 0.000 description 1
- LNPXKFRVZLTIKX-UHFFFAOYSA-N CON=C(C)C1=C(C)SC(C)=C1CS(=O)(=O)C1=NOC(C)(C)C1 Chemical compound CON=C(C)C1=C(C)SC(C)=C1CS(=O)(=O)C1=NOC(C)(C)C1 LNPXKFRVZLTIKX-UHFFFAOYSA-N 0.000 description 1
- 241000217446 Calystegia sepium Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 235000006719 Cassia obtusifolia Nutrition 0.000 description 1
- 244000277285 Cassia obtusifolia Species 0.000 description 1
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
- 241000207894 Convolvulus arvensis Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 240000008853 Datura stramonium Species 0.000 description 1
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 1
- 235000005476 Digitaria cruciata Nutrition 0.000 description 1
- 235000006830 Digitaria didactyla Nutrition 0.000 description 1
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 240000004725 Echinochloa crus-galli var. crus-galli Species 0.000 description 1
- 244000025670 Eleusine indica Species 0.000 description 1
- 244000248416 Fagopyrum cymosum Species 0.000 description 1
- 241001289522 Fallopia Species 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 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 1
- 241000207890 Ipomoea purpurea Species 0.000 description 1
- 206010024229 Leprosy Diseases 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 241000218922 Magnoliophyta Species 0.000 description 1
- 240000006959 Melochia corchorifolia Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000590428 Panacea Species 0.000 description 1
- 240000006928 Persicaria lapathifolia Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 239000005604 Prosulfuron Substances 0.000 description 1
- LTUNNEGNEKBSEH-UHFFFAOYSA-N Prosulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)CCC(F)(F)F)=N1 LTUNNEGNEKBSEH-UHFFFAOYSA-N 0.000 description 1
- 241000219782 Sesbania Species 0.000 description 1
- 235000017016 Setaria faberi Nutrition 0.000 description 1
- 241000820191 Setaria magna Species 0.000 description 1
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 235000006923 Sorghum x drummondii Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- NKWPZUCBCARRDP-UHFFFAOYSA-L calcium bicarbonate Chemical compound [Ca+2].OC([O-])=O.OC([O-])=O NKWPZUCBCARRDP-UHFFFAOYSA-L 0.000 description 1
- 229910000020 calcium bicarbonate Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 230000001149 cognitive effect Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000012364 cultivation method Methods 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- GDQVXTACQLHVPB-UHFFFAOYSA-N ethyl 1-(difluoromethyl)pyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NN(C(F)F)C=1 GDQVXTACQLHVPB-UHFFFAOYSA-N 0.000 description 1
- SIALOQYKFQEKOG-UHFFFAOYSA-N ethyl 3,3-diethoxypropanoate Chemical compound CCOC(OCC)CC(=O)OCC SIALOQYKFQEKOG-UHFFFAOYSA-N 0.000 description 1
- CBDPWKVOPADMJC-UHFFFAOYSA-N ethyl 4,4-difluoro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)C(F)F CBDPWKVOPADMJC-UHFFFAOYSA-N 0.000 description 1
- FFYIPODLFCOCSQ-UHFFFAOYSA-N ethyl 5-chloro-3-methyl-1,2-thiazole-4-carboxylate Chemical compound CCOC(=O)C=1C(C)=NSC=1Cl FFYIPODLFCOCSQ-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 235000013847 iso-butane Nutrition 0.000 description 1
- 150000002546 isoxazolidines Chemical class 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
- 239000010410 layer Substances 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 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
- 150000004702 methyl esters Chemical class 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 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
- 230000008635 plant growth Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000010298 pulverizing process Methods 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
- 239000004576 sand Substances 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
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 238000003971 tillage Methods 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000011144 upstream manufacturing Methods 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
- 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002230028 | 2002-08-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL375112A1 PL375112A1 (en) | 2005-11-28 |
| PL207304B1 true PL207304B1 (pl) | 2010-11-30 |
Family
ID=31711670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL375112A PL207304B1 (pl) | 2002-08-07 | 2003-08-07 | Kompozycja chwastobójcza |
Country Status (14)
Families Citing this family (88)
| 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 |
| AU2005237241B2 (en) * | 2004-04-30 | 2011-04-07 | Syngenta Limited | Herbicidal composition |
| 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 |
| WO2007003296A1 (de) * | 2005-07-06 | 2007-01-11 | Bayer Cropscience Ag | Herbizid-safener-kombination |
| 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 |
| 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 |
| AU2009224731B2 (en) * | 2008-03-10 | 2014-05-08 | Basf Se | Herbicidal compositions comprising pyroxasulfone |
| DK2280605T3 (da) * | 2008-03-11 | 2014-10-06 | Basf Se | Herbicide sammensætninger, der omfatter pyroxasulfon |
| JP2011513462A (ja) * | 2008-03-12 | 2011-04-28 | ビーエーエスエフ ソシエタス・ヨーロピア | ピロキサスルホンを含む除草剤組成物 |
| TW200944127A (en) * | 2008-03-14 | 2009-11-01 | Basf Se | Herbicidal compositions comprising pyroxasulfone |
| WO2009115490A2 (en) * | 2008-03-17 | 2009-09-24 | Basf Se | Herbicidal compositions comprising pyroxasulfone v |
| EA201001454A1 (ru) * | 2008-03-18 | 2011-06-30 | Басф Се | Гербицидные композиции, содержащие пироксасульфон 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 |
| 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 |
| CN102906073B (zh) | 2010-05-20 | 2015-11-25 | 拜耳知识产权有限责任公司 | 1-烷基-3-二氟甲基-5-羟基吡唑的制备方法 |
| WO2011151383A1 (en) | 2010-06-03 | 2011-12-08 | Bayer Cropscience Ag | O-cyclopropylcyclohexyl-carboxanilides and their use as fungicides |
| PL2576517T3 (pl) | 2010-06-03 | 2015-06-30 | Bayer Ip Gmbh | N-[(het)aryloalkilo)]pirazolo(tio)karboksyamidy i ich analogi heteropodstawione |
| CN102933556B (zh) | 2010-06-03 | 2015-08-26 | 拜尔农科股份公司 | N-[(杂)芳基乙基]吡唑(硫代)羧酰胺及其杂取代的类似物 |
| 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 |
| KR20130129203A (ko) | 2010-10-21 | 2013-11-27 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | Ｎ-벤질 헤테로시클릭 카르복사미드 |
| CA2815117A1 (en) | 2010-11-02 | 2012-05-10 | Bayer Intellectual Property Gmbh | N-hetarylmethyl pyrazolylcarboxamides |
| EP2640706B1 (en) | 2010-11-15 | 2017-03-01 | Bayer Intellectual Property GmbH | N-aryl pyrazole(thio)carboxamides |
| MX2013005407A (es) | 2010-11-15 | 2013-07-03 | Bayer Ip Gmbh | 5-halopirazolcarboxamidas. |
| WO2012065945A1 (en) | 2010-11-15 | 2012-05-24 | Bayer Cropscience Ag | 5-halogenopyrazole(thio)carboxamides |
| WO2012065932A1 (en) | 2010-11-15 | 2012-05-24 | Bayer Cropscience Ag | Decahydro-1,4-methanonaphthalen carboxamides |
| JP5927055B2 (ja) | 2011-06-24 | 2016-05-25 | 石原産業株式会社 | 除草組成物 |
| KR101931846B1 (ko) * | 2011-10-18 | 2018-12-21 | 에프엠씨 코포레이션 | 흄드 산화 알루미늄을 함유하는 안정한 제제 |
| US8962525B2 (en) * | 2011-10-18 | 2015-02-24 | Fmc Corporation | Stable formulations containing fumed aluminum oxide |
| EP2662361A1 (en) | 2012-05-09 | 2013-11-13 | Bayer CropScience AG | Pyrazol indanyl carboxamides |
| EP2662364A1 (en) | 2012-05-09 | 2013-11-13 | Bayer CropScience AG | Pyrazole tetrahydronaphthyl carboxamides |
| 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 |
| EP2662362A1 (en) | 2012-05-09 | 2013-11-13 | Bayer CropScience AG | Pyrazole indanyl carboxamides |
| EP2662360A1 (en) | 2012-05-09 | 2013-11-13 | Bayer CropScience AG | 5-Halogenopyrazole indanyl carboxamides |
| CA2874425C (en) | 2012-05-24 | 2020-07-14 | Bayer Cropscience Ag | Herbicidal compositions comprising n-(tetrazol-5-yl)- or n-(triazol-5-yl)arylcarboxamides |
| UA118765C2 (uk) | 2013-08-09 | 2019-03-11 | Байєр Кропсайєнс Акцієнгезелльшафт | Третинні гербіцидні комбінації, що містять дві сульфонілсечовини |
| US10111435B2 (en) | 2013-10-25 | 2018-10-30 | Bayer Cropscience Aktiengesellschaft | Herbicidal compositions containing N-(1,3,4-oxadiazol-2-yl)-aryl carboxylic acid amides |
| 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 |
| CN108929319B (zh) * | 2017-05-22 | 2019-07-09 | 东莞东阳光科研发有限公司 | 异噁唑啉衍生物及其在农业中的应用 |
| WO2019062802A1 (en) * | 2017-09-28 | 2019-04-04 | Dongguan Hec Tech R & D Co., Ltd. | ISOXAZOLINE DERIVATIVES AND USES THEREOF IN AN AGRICULTURAL APPLICATION |
| 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 |
| CN113749106A (zh) * | 2018-02-02 | 2021-12-07 | 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 |
| WO2019223664A1 (en) * | 2018-05-22 | 2019-11-28 | Dongguan HEC Pesticides R&D Co., Ltd. | Oxazoline derivatives and uses in agriculture thereof |
| 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 |
| CN111574509B (zh) * | 2019-02-18 | 2021-08-31 | 宁夏苏融达化工有限公司 | 异噁唑啉衍生物及其在农业中的应用 |
| WO2020240392A1 (en) * | 2019-05-24 | 2020-12-03 | Pi Industries Limited | Process for preparation of pyroxasulfone |
| US20230012374A1 (en) * | 2019-10-31 | 2023-01-12 | Kumiai Chemical Industry Co., Ltd. | Process for producing herbicide and 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 |
| GB2603771A (en) * | 2021-02-11 | 2022-08-17 | Rotam Agrochem Int Co Ltd | Novel crystalline form of pyroxa-sulfone, methods for its preparation and use of the same |
| 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 |
| BR112023023729A2 (pt) * | 2021-05-27 | 2024-02-20 | Upl Ltd | Novo intermediário para preparação de piroxasulfona |
| AU2023250443A1 (en) * | 2022-04-08 | 2024-10-10 | 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 |
| CN114989157A (zh) * | 2022-06-28 | 2022-09-02 | 安徽久易农业股份有限公司 | 一种砜吡草唑的晶型a及其制备方法和应用 |
| 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 |
| US20250248394A1 (en) | 2022-07-13 | 2025-08-07 | 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 |
| CN116655536A (zh) * | 2023-05-16 | 2023-08-29 | 天津大学 | 一类n1-芳基-3-氟烷基-5-氟吡唑类化合物、其制备方法及应用 |
| 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 |
Family Cites Families (10)
| 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 |
| PL197326B1 (pl) * | 1998-06-16 | 2008-03-31 | Basf Ag | Mieszanina chwastobójcza, środek chwastobójczy, sposób jego wytwarzania i sposób zwalczania niepożądanej roślinności |
| JP4465133B2 (ja) * | 2001-02-08 | 2010-05-19 | 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これを有効成分とする除草剤 |
| US7875606B2 (en) * | 2001-06-21 | 2011-01-25 | Ihara Chemical Industry Co., Ltd. | Izoxazoline derivative and herbicide |
| 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 |
-
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 PA PA20038579501A patent/PA8579501A1/es unknown
- 2003-08-05 PE PE2003000771A patent/PE20040373A1/es active IP Right Grant
- 2003-08-06 AR AR20030102825A patent/AR040809A1/es active IP Right Grant
- 2003-08-07 WO PCT/JP2003/010073 patent/WO2004014138A1/ja active Application Filing
- 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 AU AU2003254863A patent/AU2003254863A1/en not_active Abandoned
-
2005
- 2005-09-16 IN IN58KON2005 patent/IN2005KN00058A/en unknown
-
2007
- 2007-06-05 IN IN2033KO2007 patent/IN2007KO02033A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US7833939B2 (en) | 2010-11-16 |
| IN2005KN00058A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2006-01-06 |
| BR0313241B1 (pt) | 2018-01-09 |
| TWI309967B (en) | 2009-05-21 |
| WO2004014138A1 (ja) | 2004-02-19 |
| TW200406154A (en) | 2004-05-01 |
| PL375112A1 (en) | 2005-11-28 |
| JP4789101B2 (ja) | 2011-10-12 |
| PA8579501A1 (es) | 2005-02-04 |
| PE20040373A1 (es) | 2004-08-27 |
| IN2007KO02033A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2009-04-10 |
| JPWO2004014138A1 (ja) | 2005-11-24 |
| UA78071C2 (en) | 2007-02-15 |
| AU2003254863A1 (en) | 2004-02-25 |
| BR0313241A (pt) | 2005-08-09 |
| UY27909A1 (es) | 2004-02-27 |
| US20050256004A1 (en) | 2005-11-17 |
| AR040809A1 (es) | 2005-04-20 |
| MY132698A (en) | 2007-10-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PL207304B1 (pl) | Kompozycja chwastobójcza | |
| RU2237664C2 (ru) | Изоксазолиновые производные и гербициды, содержащие их в качестве активных ингредиентов | |
| RU2042667C1 (ru) | Производные 4-бензоилпиразола | |
| CN113105405B (zh) | 一种羧酸衍生物取代的亚氨基芳基化合物及其制备方法、除草组合物和应用 | |
| KR880000155B1 (ko) | 2-치환페닐-4, 5, 6, 7-데트라하이드로-2h-인다졸류의 제조방법 | |
| RO111076B1 (ro) | Derivati 2-cian-1,3-diona, procedee de preparare a acestora, compozitie erbicida si metoda pentru controlul cresterii buruienilor | |
| KR0155560B1 (ko) | 우라실 유도체, 그의 제법 및 용도 | |
| RO111679B1 (ro) | Derivati de 4-benzoilizoxazol, procedee pentru prepararea acestora, compozitii erbicide si metoda pentru controlul cresterii buruienilor | |
| RU2066321C1 (ru) | Производные пиридина или их соли, способ их получения, гербицидная композиция и способ уничтожения сорняков | |
| RU2670439C2 (ru) | Производное замещенного пиразолилпиразола и его применение в качестве гербицида | |
| US4702764A (en) | Carbamoyltriazoles, and their production and use | |
| WO2015022924A1 (ja) | 置換ピラゾリルピラゾール誘導体とその除草剤としての使用 | |
| HRP940053A2 (en) | New 4-benzoylysoxazole derivatives, process for the preparation thereof, compositions containing them and their use as herbicides | |
| KR910001130B1 (ko) | 벤조트리아졸의 제조방법 | |
| JP2004002324A (ja) | 除草剤組成物 | |
| RU2056413C1 (ru) | Иминотиазолины, способы их получения, гербицидная композиция, способ уничтожения нежелательных сорняков | |
| EP0354766B1 (en) | 5-substituted-2,4-diphenyl-pyrimidine derivatives, their production and herbicidal use | |
| JP3084102B2 (ja) | 相乗的除草剤組成物 | |
| AU2002318801B2 (en) | Herbicide containing substituted pyrazole derivative as active ingredient | |
| EP0548593B1 (en) | Tetrahydrofuran derivative and herbicide containing the same as effective ingredient | |
| EP0116928A1 (en) | Pyridotriazolium compounds, and their production and use | |
| KR0163611B1 (ko) | 페닐이미다졸 유도체, 이의 제조방법 및 이를 포함하는 제초제 | |
| KR20000070876A (ko) | 페녹시아세트산 유도체 및 제초제로서의 그의 용도 | |
| US4846882A (en) | Herbicidal aryl tetrahydrophthalimides | |
| HUT59682A (en) | Herbicide compositions containing triazolo-pyridazine derivatives as active components and process for producing the active components |