CN1131143A - 以n-(4-氟-苯基)-n-异丙基-氯乙酰胺为主的除草组合物及该化合物的制备方法 - Google Patents
以n-(4-氟-苯基)-n-异丙基-氯乙酰胺为主的除草组合物及该化合物的制备方法 Download PDFInfo
- Publication number
- CN1131143A CN1131143A CN95120571A CN95120571A CN1131143A CN 1131143 A CN1131143 A CN 1131143A CN 95120571 A CN95120571 A CN 95120571A CN 95120571 A CN95120571 A CN 95120571A CN 1131143 A CN1131143 A CN 1131143A
- Authority
- CN
- China
- Prior art keywords
- compound
- fluoro
- sec
- propyl
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 239000000203 mixture Substances 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims abstract description 7
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 6
- 241000196324 Embryophyta Species 0.000 claims abstract description 29
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 5
- 239000011230 binding agent Substances 0.000 claims abstract description 3
- 239000003701 inert diluent Substances 0.000 claims abstract description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 2
- 238000009333 weeding Methods 0.000 claims description 2
- -1 for example Substances 0.000 abstract description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 12
- 235000002017 Zea mays subsp mays Nutrition 0.000 abstract description 4
- BKSIERMKNBPHJD-UHFFFAOYSA-N 2-chloro-n-(4-fluorophenyl)-n-propan-2-ylacetamide Chemical compound ClCC(=O)N(C(C)C)C1=CC=C(F)C=C1 BKSIERMKNBPHJD-UHFFFAOYSA-N 0.000 abstract 1
- RMXBOQCXULAXBO-UHFFFAOYSA-N 4-fluoro-n-propan-2-ylaniline Chemical compound CC(C)NC1=CC=C(F)C=C1 RMXBOQCXULAXBO-UHFFFAOYSA-N 0.000 abstract 1
- 240000008042 Zea mays Species 0.000 abstract 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 abstract 1
- 235000009973 maize Nutrition 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 7
- 239000000975 dye Substances 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 244000025254 Cannabis sativa Species 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000209149 Zea Species 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 240000001592 Amaranthus caudatus Species 0.000 description 3
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 3
- 241000801118 Lepidium Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000207763 Solanum Species 0.000 description 3
- 235000002634 Solanum Nutrition 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- 235000005781 Avena Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 241000339490 Brachyachne Species 0.000 description 2
- 244000056139 Brassica cretica Species 0.000 description 2
- 235000003351 Brassica cretica Nutrition 0.000 description 2
- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 241000192043 Echinochloa Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000209117 Panicum Species 0.000 description 2
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 2
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 2
- 241001092090 Pittosporum Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 235000012735 amaranth Nutrition 0.000 description 2
- 239000004178 amaranth Substances 0.000 description 2
- 239000012874 anionic emulsifier Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 230000008029 eradication Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011785 micronutrient Substances 0.000 description 2
- 235000013369 micronutrients Nutrition 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- 239000011146 organic particle Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- IPPAUTOBDWNELX-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical group C1=C([N+]([O-])=O)C(C(=O)OCC(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 IPPAUTOBDWNELX-UHFFFAOYSA-N 0.000 description 1
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical compound O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 description 1
- XTVIFVALDYTCLL-UHFFFAOYSA-N 2,3,5-trichloro-1h-pyridin-4-one Chemical compound ClC1=CNC(Cl)=C(Cl)C1=O XTVIFVALDYTCLL-UHFFFAOYSA-N 0.000 description 1
- 239000002794 2,4-DB Substances 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 1
- YUVKUEAFAVKILW-UHFFFAOYSA-N 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 YUVKUEAFAVKILW-UHFFFAOYSA-N 0.000 description 1
- ITRMZMMDHHMHFY-UHFFFAOYSA-N 2-chloro-n-(1-methoxypropan-2-yl)-n-phenylacetamide Chemical compound COCC(C)N(C(=O)CCl)C1=CC=CC=C1 ITRMZMMDHHMHFY-UHFFFAOYSA-N 0.000 description 1
- IRCMYGHHKLLGHV-UHFFFAOYSA-N 2-ethoxy-3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl methanesulfonate Chemical compound C1=C(OS(C)(=O)=O)C=C2C(C)(C)C(OCC)OC2=C1 IRCMYGHHKLLGHV-UHFFFAOYSA-N 0.000 description 1
- ABOOPXYCKNFDNJ-UHFFFAOYSA-N 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-UHFFFAOYSA-N 0.000 description 1
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- QQOGZMUZAZWLJH-UHFFFAOYSA-N 5-[2-chloro-6-fluoro-4-(trifluoromethyl)phenoxy]-n-ethylsulfonyl-2-nitrobenzamide Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)CC)=CC(OC=2C(=CC(=CC=2F)C(F)(F)F)Cl)=C1 QQOGZMUZAZWLJH-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 description 1
- 241000427159 Achyranthes Species 0.000 description 1
- 241000209136 Agropyron Species 0.000 description 1
- 241000743339 Agrostis Species 0.000 description 1
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 1
- 240000002234 Allium sativum Species 0.000 description 1
- 239000003666 Amidosulfuron Substances 0.000 description 1
- CTTHWASMBLQOFR-UHFFFAOYSA-N Amidosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)N(C)S(C)(=O)=O)=N1 CTTHWASMBLQOFR-UHFFFAOYSA-N 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 241000404028 Anthemis Species 0.000 description 1
- 241001666377 Apera Species 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010576 Artemisia cina Nutrition 0.000 description 1
- 235000005340 Asparagus officinalis Nutrition 0.000 description 1
- QGQSRQPXXMTJCM-UHFFFAOYSA-N Benfuresate Chemical compound CCS(=O)(=O)OC1=CC=C2OCC(C)(C)C2=C1 QGQSRQPXXMTJCM-UHFFFAOYSA-N 0.000 description 1
- 239000005476 Bentazone Substances 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 101000742062 Bos taurus Protein phosphatase 1G Proteins 0.000 description 1
- 241000611157 Brachiaria Species 0.000 description 1
- 239000005489 Bromoxynil Substances 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- 241000217446 Calystegia sepium Species 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 244000036828 Carduus nutans Species 0.000 description 1
- 240000004385 Centaurea cyanus Species 0.000 description 1
- 235000005940 Centaurea cyanus Nutrition 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- 235000000509 Chenopodium ambrosioides Nutrition 0.000 description 1
- 239000005493 Chloridazon (aka pyrazone) Substances 0.000 description 1
- 239000005494 Chlorotoluron Substances 0.000 description 1
- 239000005496 Chlorsulfuron Substances 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 244000192528 Chrysanthemum parthenium Species 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- 241000132536 Cirsium Species 0.000 description 1
- 241000675108 Citrus tangerina Species 0.000 description 1
- 239000005497 Clethodim Substances 0.000 description 1
- 239000005499 Clomazone Substances 0.000 description 1
- 239000005500 Clopyralid Substances 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 235000010071 Cucumis prophetarum Nutrition 0.000 description 1
- 244000024469 Cucumis prophetarum Species 0.000 description 1
- 241000219122 Cucurbita Species 0.000 description 1
- DFCAFRGABIXSDS-UHFFFAOYSA-N Cycloate Chemical compound CCSC(=O)N(CC)C1CCCCC1 DFCAFRGABIXSDS-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000005501 Cycloxydim Substances 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- 241000721045 Daubentonia Species 0.000 description 1
- 241000208175 Daucus Species 0.000 description 1
- 239000005507 Diflufenican Substances 0.000 description 1
- YUBJPYNSGLJZPQ-UHFFFAOYSA-N Dithiopyr Chemical compound CSC(=O)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=O)SC)=C1CC(C)C YUBJPYNSGLJZPQ-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 1
- 235000001950 Elaeis guineensis Nutrition 0.000 description 1
- 244000127993 Elaeis melanococca Species 0.000 description 1
- 241000202829 Eleocharis Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- 244000025670 Eleusine indica Species 0.000 description 1
- 241001517310 Eria Species 0.000 description 1
- BXEHUCNTIZGSOJ-UHFFFAOYSA-N Esprocarb Chemical compound CC(C)C(C)N(CC)C(=O)SCC1=CC=CC=C1 BXEHUCNTIZGSOJ-UHFFFAOYSA-N 0.000 description 1
- 239000005512 Ethofumesate Substances 0.000 description 1
- 241000234642 Festuca Species 0.000 description 1
- 241001290564 Fimbristylis Species 0.000 description 1
- 239000005533 Fluometuron Substances 0.000 description 1
- 239000005558 Fluroxypyr Substances 0.000 description 1
- 241000748465 Galinsoga Species 0.000 description 1
- 235000014820 Galium aparine Nutrition 0.000 description 1
- 240000005702 Galium aparine Species 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 239000005562 Glyphosate Substances 0.000 description 1
- 235000009438 Gossypium Nutrition 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- CAWXEEYDBZRFPE-UHFFFAOYSA-N Hexazinone Chemical compound O=C1N(C)C(N(C)C)=NC(=O)N1C1CCCCC1 CAWXEEYDBZRFPE-UHFFFAOYSA-N 0.000 description 1
- 235000015466 Hierochloe odorata Nutrition 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 241001327265 Ischaemum Species 0.000 description 1
- 239000005570 Isoxaben Substances 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 241000520028 Lamium Species 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- 241000208204 Linum Species 0.000 description 1
- 241000209082 Lolium Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 239000005574 MCPA Substances 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- 239000005580 Metazachlor Substances 0.000 description 1
- RRVIAQKBTUQODI-UHFFFAOYSA-N Methabenzthiazuron Chemical compound C1=CC=C2SC(N(C)C(=O)NC)=NC2=C1 RRVIAQKBTUQODI-UHFFFAOYSA-N 0.000 description 1
- 239000005583 Metribuzin Substances 0.000 description 1
- 239000005584 Metsulfuron-methyl Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 235000003990 Monochoria hastata Nutrition 0.000 description 1
- 240000000178 Monochoria vaginalis Species 0.000 description 1
- 240000005561 Musa balbisiana Species 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- 241001504654 Mustela nivalis Species 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- FCSLKRVBOXMLOR-UHFFFAOYSA-N N1CCNCC1.C1=CC=CC=C1 Chemical compound N1CCNCC1.C1=CC=CC=C1 FCSLKRVBOXMLOR-UHFFFAOYSA-N 0.000 description 1
- FDUWFRCKTQJMPV-UHFFFAOYSA-N N=1NC(C=CC1)=O.[Cl] Chemical compound N=1NC(C=CC1)=O.[Cl] FDUWFRCKTQJMPV-UHFFFAOYSA-N 0.000 description 1
- MBXGROBTFFXPFK-UHFFFAOYSA-N N=1NC(C=CC1)=O.[F] Chemical compound N=1NC(C=CC1)=O.[F] MBXGROBTFFXPFK-UHFFFAOYSA-N 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 239000005590 Oxyfluorfen Substances 0.000 description 1
- OQMBBFQZGJFLBU-UHFFFAOYSA-N Oxyfluorfen Chemical compound C1=C([N+]([O-])=O)C(OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 OQMBBFQZGJFLBU-UHFFFAOYSA-N 0.000 description 1
- 241001213934 Panicum schinzii Species 0.000 description 1
- 235000011096 Papaver Nutrition 0.000 description 1
- 240000001090 Papaver somniferum Species 0.000 description 1
- 241001330453 Paspalum Species 0.000 description 1
- 239000005591 Pendimethalin Substances 0.000 description 1
- 241000219833 Phaseolus Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 244000292693 Poa annua Species 0.000 description 1
- 241000205407 Polygonum Species 0.000 description 1
- 235000006386 Polygonum aviculare Nutrition 0.000 description 1
- 244000292697 Polygonum aviculare Species 0.000 description 1
- 241000219295 Portulaca Species 0.000 description 1
- 239000005603 Prosulfocarb Substances 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 244000179750 Psoralea glandulosa Species 0.000 description 1
- VXMNDQDDWDDKOQ-UHFFFAOYSA-N Pyrazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C(O)=O)C)=N1 VXMNDQDDWDDKOQ-UHFFFAOYSA-N 0.000 description 1
- 239000005606 Pyridate Substances 0.000 description 1
- JTZCTMAVMHRNTR-UHFFFAOYSA-N Pyridate Chemical compound CCCCCCCCSC(=O)OC1=CC(Cl)=NN=C1C1=CC=CC=C1 JTZCTMAVMHRNTR-UHFFFAOYSA-N 0.000 description 1
- 239000005608 Quinmerac Substances 0.000 description 1
- 241000218206 Ranunculus Species 0.000 description 1
- 241000209051 Saccharum Species 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 241000780602 Senecio Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- CSPPKDPQLUUTND-NBVRZTHBSA-N Sethoxydim Chemical compound CCO\N=C(/CCC)C1=C(O)CC(CC(C)SCC)CC1=O CSPPKDPQLUUTND-NBVRZTHBSA-N 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 235000006745 Sonchus oleraceus Nutrition 0.000 description 1
- 244000113428 Sonchus oleraceus Species 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 240000001949 Taraxacum officinale Species 0.000 description 1
- 235000005187 Taraxacum officinale ssp. officinale Nutrition 0.000 description 1
- 239000005621 Terbuthylazine Substances 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000005624 Tralkoxydim Substances 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- 239000005625 Tri-allate Substances 0.000 description 1
- MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical compound CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 description 1
- IBZHOAONZVJLOB-UHFFFAOYSA-N Tridiphane Chemical compound ClC1=CC(Cl)=CC(C2(CC(Cl)(Cl)Cl)OC2)=C1 IBZHOAONZVJLOB-UHFFFAOYSA-N 0.000 description 1
- 241000219793 Trifolium Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 241000219422 Urtica Species 0.000 description 1
- 241001573053 Vandellia Species 0.000 description 1
- 240000005592 Veronica officinalis Species 0.000 description 1
- 241000219873 Vicia Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 241000405217 Viola <butterfly> Species 0.000 description 1
- 241001506766 Xanthium Species 0.000 description 1
- FDTAOSBGUZWNSN-UHFFFAOYSA-N [Cl].[F].N1C=CC=C1 Chemical compound [Cl].[F].N1C=CC=C1 FDTAOSBGUZWNSN-UHFFFAOYSA-N 0.000 description 1
- CAWBOJFIANSPRE-UHFFFAOYSA-N [I].C(C(=O)O)(=O)O Chemical compound [I].C(C(=O)O)(=O)O CAWBOJFIANSPRE-UHFFFAOYSA-N 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 244000193174 agave Species 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- ORFLOUYIJLPLPL-WOJGMQOQSA-N alloxydim Chemical compound CCC\C(=N/OCC=C)C1=C(O)CC(C)(C)C(C(=O)OC)C1=O ORFLOUYIJLPLPL-WOJGMQOQSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- QLULGSLAHXLKSR-UHFFFAOYSA-N azane;phosphane Chemical compound N.P QLULGSLAHXLKSR-UHFFFAOYSA-N 0.000 description 1
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 1
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- GGWHBJGBERXSLL-NBVRZTHBSA-N chembl113137 Chemical compound C1C(=O)C(C(=N/OCC)/CCC)=C(O)CC1C1CSCCC1 GGWHBJGBERXSLL-NBVRZTHBSA-N 0.000 description 1
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 1
- RIUXZHMCCFLRBI-UHFFFAOYSA-N chlorimuron Chemical compound COC1=CC(Cl)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 RIUXZHMCCFLRBI-UHFFFAOYSA-N 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 description 1
- VJYIFXVZLXQVHO-UHFFFAOYSA-N chlorsulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- SILSDTWXNBZOGF-JWGBMQLESA-N clethodim Chemical compound CCSC(C)CC1CC(O)=C(C(CC)=NOC\C=C\Cl)C(=O)C1 SILSDTWXNBZOGF-JWGBMQLESA-N 0.000 description 1
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 description 1
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 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 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- QMTNOLKHSWIQBE-FGTMMUONSA-N exo-(+)-cinmethylin Chemical compound O([C@H]1[C@]2(C)CC[C@@](O2)(C1)C(C)C)CC1=CC=CC=C1C QMTNOLKHSWIQBE-FGTMMUONSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
- OQZCSNDVOWYALR-UHFFFAOYSA-N flurochloridone Chemical compound FC(F)(F)C1=CC=CC(N2C(C(Cl)C(CCl)C2)=O)=C1 OQZCSNDVOWYALR-UHFFFAOYSA-N 0.000 description 1
- MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical compound NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 description 1
- BGZZWXTVIYUUEY-UHFFFAOYSA-N fomesafen Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 BGZZWXTVIYUUEY-UHFFFAOYSA-N 0.000 description 1
- 239000004459 forage Substances 0.000 description 1
- 235000004611 garlic Nutrition 0.000 description 1
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
- 229940097068 glyphosate Drugs 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- KQSBZNJFKWOQQK-UHFFFAOYSA-N hystazarin Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2 KQSBZNJFKWOQQK-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 description 1
- PMHURSZHKKJGBM-UHFFFAOYSA-N isoxaben Chemical compound O1N=C(C(C)(CC)CC)C=C1NC(=O)C1=C(OC)C=CC=C1OC PMHURSZHKKJGBM-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- CONWAEURSVPLRM-UHFFFAOYSA-N lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 description 1
- RPUSRLKKXPQSGP-UHFFFAOYSA-N methyl 3-phenylpropanoate Chemical compound COC(=O)CCC1=CC=CC=C1 RPUSRLKKXPQSGP-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical compound [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 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 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- FJSMZHRHSKLZBN-UHFFFAOYSA-N piperazine;toluene Chemical compound C1CNCCN1.CC1=CC=CC=C1 FJSMZHRHSKLZBN-UHFFFAOYSA-N 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
- C07C233/15—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及已知式(I)化合物N-(4-氟-苯基)-N-异丙基-氯乙酰胺作为选择性除草组合物活性物质的用途，例如用于玉米栽培中的除草，以及这种活性化合物的新制备方法。
在20-150℃温度，一种如甲苯的惰性稀释剂存在，不加酸结合剂的条件下N-异丙基-4-氟-苯胺与大约等摩尔的氯乙酰氯，发生反应可以获得收率很高的式(I)化合物。
Description
本发明涉及已知化合物N-(4-氟-苯基)-N-异丙基-氯乙酰胺用作选择性除草组合物活性化合物的用途及该化合物的新的制备方法。
N-(4-氟-苯基)-N-异丙基-氯乙酰胺作为农用化学物质的一个中间体已经公开(参见DE-OS(德国公开说明书)2633159，美国专利4140774，美国专利4418021)。但是，上述化合物作为一种除草剂至今尚未公开。
现在发现以下式(I)化合物N-(4-氟-苯基)-N-异丙基-氯乙酰胺非常适合用于选择性除众多栽培植物的杂草。
迄今为止，在吡啶存在下用N-异丙基-4-氟-苯胺与氯乙酰氯反应制备式(I)化合物的方法已经公开。但是发现，以工业规模实现盐酸吡啶反应生成吡啶非常复杂。
另外，通过N-异丙基-苯胺和氯乙酸和磷酰氯或三氯化磷反应制备其类似物化合物N-(异丙基-苯基)-氯乙酰胺也已经公开(参见美国专利3960948)。但是，这个制备方法的产率不太令人满意，而且还必须通过沉淀磷酸盐处理含磷的废水。
现在发现，在20℃—150℃温度下，在一种如甲苯的惰性稀释剂存在下，不加酸结合剂的条件下，N-异丙基-4-氟-苯胺与大约相等摩尔量的氯乙酰氯发生反应，所获得的式(I)化合物的收率很高。
这种制备方法不产生废水，所释放的氯化氢可以再为他用。
合成式(I)化合物的反应过程可以用下列反应式概括：
制备式(I)化合物所需的原料物质均为已知化合物。
式(I)化合物可以用于脱叶剂，干燥剂，阔叶植物的破坏剂，特别是用作除草剂。这里的杂草最广义地理解为生长在不需要地方的所有植物。
例如，式(I)化合物可以用于以下相关植物：
下列属的双子叶杂草：芥属，独行菜属，猪殃殃属，繁缕属，母菊属，春黄菊属，牛膝菊属藜属，荨麻属，千里光属，苋菜红属，马齿苋属，苍耳属，旋花属，番藷属，蓼属，田菁属，土荆芥属，蓟属，飞廉属，苦苣属，茄属，蔊菜属，节节菜属，母草属，野芝麻属，婆婆纳属，麻属，亦模属，茄属，堇菜属，黄鼠狼花属，罂粟属，矢车菊属，车轴草属，毛茛属，蒲公英属。
下列属的双子叶栽培植物：棉属，大豆属，恭菜属，胡萝卜属，菜豆属，碗豆属，茄属，亚麻属，番藷属，巢菜属，烟草属，番茄属，落花生属，芥属，萵苣属，黄瓜属和南瓜属。
下列属的单子叶杂草：稗属，狗尾草属，黍属，马唐属，梯牧草属，早熟禾属，羊茅属，蟋蟀草属，臂形草属，黑麦草属，雀麦属，燕麦属，莎草属，蜀黍属，冰草属，狗牙根属，雨久花属，飘拂草属，慈菇属，荸荠属，草属，雀稗属，鸭嘴草属，尖瓣花属，龙爪茅属，剪股颖属，看麦娘属，Apera
下列属的单子叶载培植物：稻米属，玉米属，小麦属，大麦属，燕麦属，黑麦属，蜀黍属，黍属，甘蔗属，凤梨属，天门冬属，大蒜属。
但是，式(I)化合物的用途不只限于这些属，还能以同样的方式扩展到其它植物。
依浓度而定，式(I)化合物适合于全部去除如长在工地，铁轨，有或没有植树的道路和广场上的杂草。同样，这种化合物可用于去除多年生栽培植物的杂草，例如，种植的树林，栽培的装饰树，果园，葡萄园，柑橘园，胡桃园，香蕉园，咖啡园，茶园，橡胶园，油棕榈园，可可园，栽培的水果和田垄以及草坪、草皮、牧场的杂草。还可用于选择性去除一年生栽培植物的杂草。
本发明的式(I)化合物特别适用于选择性去除单子叶栽培植物的单子叶和双子叶杂草。
可以将式(I)化合物转化为常用制剂，如溶液，乳液，湿粉，悬浮液，粉末，粉尘剂，膏剂可溶性粉末，颗粒，悬乳剂浓缩物，浸透有活性化合物的天然和合成物质以及包有聚合物质的微胶囊。
这些制剂可用已知的方法来制备，例如将活性化合物与增溶剂相混合，这种增容剂是液体溶剂和/或固体载体。还可选择使用表面活性剂，它们是乳化剂和/或分散剂和/或发泡剂。
如果用水作为一种增溶剂，有机溶剂也可用作辅助溶剂等。适合作液体溶剂的主要有：芳族化合物，如二甲苯，甲苯或烷基萘；氯化芳族化合物和氯化脂族烃，如氯苯，氯乙烯或二氯甲烷；脂族烃，如环己烷或链烷烃，例如石油馏分，矿物和植物油；醇类，如丁醇或二元醇以及它们的醚和酯；酮类如丙酮，甲基异丁酮或环己酮；强极性溶剂，如二甲基甲酰胺和二甲基亚砜和水。
适合作固体载体的有：铵盐和磨碎的天然矿物以及磨碎的合成矿物等。天然矿物如陶土，粘土，滑石，白垩，石英，白土，蒙脱土或硅藻土；合成矿物如高高分散性硅石，矾土和硅酸盐。适合作固体载体的颗料有：粉碎的天然岩石，无机、有机粉末的合成颗粒以及有机物的颗粒等。天然岩石如方解石，云石，浮石，海浮石和白云石；有机物颗粒如锯末，椰子壳，玉米蕊和烟草茎。适合作乳化剂和/或发泡剂的有：非离子、阴离子乳化剂，烷芳基聚乙二醇醚，烷基磺酸盐，烷基硫酸盐，芳基磺酸盐以及蛋白水解产物等。非离子、阴离子乳化剂如聚氧乙烯脂肪酸酯，聚氧乙烯脂肪醇脂。适合作分散剂的有：木素亚硫酸盐废液和甲基纤维素等。
在制剂中可以使用粘合剂如羧甲基纤维素、以粉末、颗粒或乳胶形式的天然和合成聚合物如阿拉伯树胶，多元醇，聚乙酸盐以及天然磷脂如脑磷脂和卵磷脂和合成磷脂。另外添加剂还可以是矿物油和植物油。
还可以使用着色剂，有机染料和微量营养素。着色剂如氧化铁，氧化钛和普鲁士蓝的无机颜料等。有机染料，如茜素染料，偶氮染料和金属酞菁染料。微量营养素，如铁、锰、硼、铜、钴、钼和锌盐。
活性化合物在制剂全部组分中所占的重量百分比为0.1～95％，优选0.5～90％。
用于除草时，本发明的式(I)化合物本身或它们的制剂可以与可接受的已知除草剂、成品制剂或罐装混合物相混合使用。
适合于该混合物的除草剂为已知除草剂，有酰苯胺类，如吡氟草胺和敌稗；芳基羧酸类，如敌草定，甲氧二氯苯酸和毒草定；芳基氧链烷酸(aryloxyalkanoic acids)类，如2，4-D，2，4-DB，2，4-DP，氟草烟MCPA，MCPP和乙氯草定；芳氧基-苯氧基-链烷酯类，如2，4-滴苯丙酸甲酯，噁唑禾草灵，吡氟禾草灵，吡氟氯禾灵和喹禾灵；氮杂苯酮类(azinones)，如氯哒酮(chloridazon)和氟哒酮；氨基甲酸酯类，如氯苯胺灵，甜草灵，甲二威灵、和苯胺灵；乙酰氯苯胺类，如杂草锁，乙基乙草胺，丁基锁，吡草胺，甲氧毒草胺，丙草胺和毒草胺；二硝基苯胺类，如磺胺乐灵，Pendimethalin和氟乐灵；二苯醚类，如三氟羧草醚，甲酯除草醚，乙羧氟草醚，氟黄胺草醚，halosafen，乳氟禾草灵和乙氧氟甲草醚；脲类，如绿麦隆，敌草降，优草隆，异丙隆，利谷隆和噻唑隆；羟胺类，如alloxydim，烯草酮，噻草酮，稀禾定和肟草酮；咪唑啉酮类，如咪草烟，咪草酯，灭草烟和灭草喹；腈类，如溴草腈，敌草腈和碘草腈；氧乙酰胺类，如苯噻草胺；磺酰脲类，如amidosulfuron，苄嘧黄隆，氯嘧黄隆，绿黄隆，醚黄隆，甲黄隆，烟嘧黄隆，氟嘧黄隆，吡嘧黄隆，噻黄隆，醚苯黄隆和苯黄隆；硫代氨基甲酸盐类，如异丁草丹，环己丹，二氯烯丹，EPTC，禾草畏，环草丹，苄草丹，thiobencarb和三氯烯丹；三嗪类，如阿特拉津，丙腈津，西玛津，西玛净，特丁草净和特丁津；三嗪酮类(triazinones)，如己苯嗪(hexazinone)，甲苯嗪和赛克嗪；其它，如氨三唑，呋草黄，苯达松，环庚草醚，异恶草酮，clopyralid，草吡唑，氟硫草定，甜菜呋，氟咯草酮，草铵膦，草甘膦，异恶草胺，pyridate，二氯喹啉酸，喹草酸，sulphosate和tridiphane。
还可以与其它已知活性化合物混合，如杀菌剂，杀虫剂，杀螨剂，杀线虫剂，鸟拒斥剂，植物营养剂和土壤改良剂。
式(I)化合物可以以它的制剂形式或经过进一步稀释制备的应用形式使用，例如，预备溶液，悬浮液，乳液，粉末，膏和颗粒。以常规方法如通过浇水，喷洒，喷雾或撒播使用。
植物出现之前和之后均可使用式(I)化合物，在播种之前可以将它掺入土壤中。
使用活性化合物的量可以在一个很大范围内变化，基本上是根据所需效果而定。通常，使用量为每公顷土壤表面积10g-10kg活性化合物，优选量为每公顷50g-5kg。
式(I)化合物的方法和用途可以用下面的实施例说明。制备方法实施例：
将15.3g(0.1摩尔)的4-氟-N-异丙基-苯胺溶于100ml甲苯，在60℃下将11.3g(0.1摩尔)的氯乙酰氯滴入搅拌好的溶液中。混合物在沸点下加热90分钟；然后，稍微冷却混合物，先在水泵真空下蒸馏，最后在油泵真空下蒸馏，仔细去掉溶剂。
得到22.9g(理论的96.5％)N-(4-氟-苯基-N-异丙基-氯乙酰胺，为澄清残余液，折射率1.5210。
用途实施例：
出现前试验
溶剂：5份重量的丙酮
乳化剂：1份重量的烷芳基聚乙二醇醚
1份重量的有效化合物与以上数量的溶剂混合，加入以上数量的乳化剂，并且用水将浓缩物稀释到所需浓度。
将试验植物的种子种入一般土壤中。24小时后，用活性化合物的制剂浇土壤。每单位面积浇水的量最好保持不变，制剂中活性化合物的浓度并不重要，只有每单位面积所用活性化合物的量才是决定性因素。3周后，与未处理对照组的生长情况相比较，用损害百分比评价这些植物的损害程度。
图表表示：
0％＝无效(类似未处理对照组)
100％＝全部破坏
试验中把式(I)化合物与具有良好耐药性的农作物如玉米等混合，表示有效除草作用(cf·表A)。
表A：出现前试验/温室
| 应用评价 | 玉米 | cynodon | Echinochloa | 狗尾草 | 苋菜红 | Galinsoga |
| 1000克/公顷(I) | 0 | 100 | 100 | 100 | 90 | 95 |
Claims (5)
1.除草组合物，其特征在于含有式(I)化合物N-(4-氟-苯基)-N-异丙基-氯乙酰胺。
2.去除杂草的方法，其特征在于把式(I)化合物N-(4-氟-苯基)-N-异丙基-氯乙酰胺作用于杂草或杂草的环境。
3.式(I)化合物N-(4-氟-苯基)-N-异丙基-氯乙酰胺除草用途。
4.除草组合物的制备方法，其特征在于把N-(4-氟-苯基)-N-异丙基-氯乙酰胺与增溶剂和/或表面活性剂混合。
5.如权利要求1所述的式(I)化合物N-(4-氟-苯基)-N-异丙基-氯乙酰胺的制备方法，其特征在于在20-150℃温度，一种惰性稀释剂存在，不加酸结合剂的条件下，把N-异丙基-4-氟-苯胺与大约相等摩尔量的氯乙酰氯反应。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4438001.1 | 1994-10-25 | ||
| DE4438001A DE4438001A1 (de) | 1994-10-25 | 1994-10-25 | Herbizide Mittel auf Basis von N-(4-Fluor-phenyl)-N-isopropylchloracetamid und Verfahren zur Herstellung dieser Verbindung |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN00101059A Division CN1107051C (zh) | 1994-10-25 | 2000-01-10 | N－(4－氟－苯基)－n－异丙基－氯乙酰胺的制备方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1131143A true CN1131143A (zh) | 1996-09-18 |
| CN1057756C CN1057756C (zh) | 2000-10-25 |
Family
ID=6531578
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN95120571A Expired - Fee Related CN1057756C (zh) | 1994-10-25 | 1995-10-25 | 一种除草组合物及其制备方法 |
| CN00101059A Expired - Lifetime CN1107051C (zh) | 1994-10-25 | 2000-01-10 | N－(4－氟－苯基)－n－异丙基－氯乙酰胺的制备方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN00101059A Expired - Lifetime CN1107051C (zh) | 1994-10-25 | 2000-01-10 | N－(4－氟－苯基)－n－异丙基－氯乙酰胺的制备方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US5639713A (zh) |
| EP (2) | EP0884304B1 (zh) |
| JP (1) | JP3817657B2 (zh) |
| KR (1) | KR100399764B1 (zh) |
| CN (2) | CN1057756C (zh) |
| DE (3) | DE4438001A1 (zh) |
| ES (2) | ES2158636T3 (zh) |
| IL (1) | IL115719A (zh) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108250095A (zh) * | 2018-01-15 | 2018-07-06 | 中国民航大学 | 一种酰胺型双子季铵盐表面活性剂的合成方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE26961E (en) * | 1968-05-27 | 1970-10-06 | Ci. aoln | |
| DE1793110A1 (de) * | 1968-08-02 | 1971-12-16 | Basf Ag | Substituierte Saeureanilide |
| CH535204A (de) * | 1969-06-07 | 1973-03-31 | Eszakmagyar Vegyimuevek | Verfahren zur Herstellung N-substituierter a-Chloracylanilide |
| GB1490985A (en) | 1974-02-14 | 1977-11-09 | Lankro Chem Ltd | Processes for the preparation of substituted chloroacylanilides |
| US4021483A (en) * | 1975-07-25 | 1977-05-03 | American Cyanamid Company | 2-Chloro-N-isopropyl-2',3'-dimethylacetanilide as a herbicidal agent |
| DE2633159C2 (de) | 1976-07-23 | 1982-05-27 | Hoechst Ag, 6000 Frankfurt | Phosphorhaltige Verbindungen, Verfahren zu ihrer Herstellung, sowie diese Verbindungen enthaltende herbizide Mittel |
| NL7700930A (nl) | 1976-02-04 | 1977-08-08 | Hoechst Ag | Plantenbeschermingsmiddel. |
| US4418021A (en) | 1977-07-13 | 1983-11-29 | Gulf Oil Corporation | N-Isopropylcarbanilylmethyl dithiophosphates |
| US4453965A (en) | 1977-07-13 | 1984-06-12 | Patel Natu R | N-Isopropylcarbanilylmethyl dithiophosphates as pre-emergent herbicides |
| JPS63119447A (ja) * | 1986-11-06 | 1988-05-24 | Hokko Chem Ind Co Ltd | アニリド誘導体および除草剤 |
| JPS63126847A (ja) * | 1986-11-17 | 1988-05-30 | Hokko Chem Ind Co Ltd | Ｎ−置換アニリン誘導体およびその製法 |
-
1994
- 1994-10-25 DE DE4438001A patent/DE4438001A1/de not_active Withdrawn
-
1995
- 1995-10-12 DE DE59505498T patent/DE59505498D1/de not_active Expired - Fee Related
- 1995-10-12 ES ES98115670T patent/ES2158636T3/es not_active Expired - Lifetime
- 1995-10-12 EP EP98115670A patent/EP0884304B1/de not_active Expired - Lifetime
- 1995-10-12 DE DE59509391T patent/DE59509391D1/de not_active Expired - Lifetime
- 1995-10-12 EP EP95116098A patent/EP0709368B1/de not_active Expired - Lifetime
- 1995-10-12 ES ES95116098T patent/ES2129727T3/es not_active Expired - Lifetime
- 1995-10-18 US US08/544,751 patent/US5639713A/en not_active Expired - Fee Related
- 1995-10-20 KR KR1019950036418A patent/KR100399764B1/ko not_active IP Right Cessation
- 1995-10-23 IL IL11571995A patent/IL115719A/xx not_active IP Right Cessation
- 1995-10-24 JP JP29888495A patent/JP3817657B2/ja not_active Expired - Lifetime
- 1995-10-25 CN CN95120571A patent/CN1057756C/zh not_active Expired - Fee Related
-
1997
- 1997-01-30 US US08/792,312 patent/US5831126A/en not_active Expired - Lifetime
-
2000
- 2000-01-10 CN CN00101059A patent/CN1107051C/zh not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE59505498D1 (de) | 1999-05-06 |
| DE4438001A1 (de) | 1996-05-02 |
| CN1275561A (zh) | 2000-12-06 |
| IL115719A (en) | 2000-06-01 |
| JP3817657B2 (ja) | 2006-09-06 |
| DE59509391D1 (de) | 2001-08-09 |
| CN1057756C (zh) | 2000-10-25 |
| EP0884304A2 (de) | 1998-12-16 |
| EP0884304A3 (de) | 1999-02-03 |
| IL115719A0 (en) | 1996-01-19 |
| KR960013199A (ko) | 1996-05-22 |
| ES2158636T3 (es) | 2001-09-01 |
| US5639713A (en) | 1997-06-17 |
| EP0709368B1 (de) | 1999-03-31 |
| EP0884304B1 (de) | 2001-07-04 |
| JPH08225407A (ja) | 1996-09-03 |
| EP0709368A1 (de) | 1996-05-01 |
| KR100399764B1 (ko) | 2003-12-06 |
| CN1107051C (zh) | 2003-04-30 |
| US5831126A (en) | 1998-11-03 |
| ES2129727T3 (es) | 1999-06-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101402876B1 (ko) | 제초성 우라실계 화합물 및 이를 포함하는 제초제 | |
| JP3959112B2 (ja) | 除草剤及び殺虫剤としての置換アミノフェニルウラシル類 | |
| JP2693774B2 (ja) | マロン酸誘導体化合物の植物の成長を抑制するための使用 | |
| JPS62483A (ja) | ３―フェニル―４―シアノピロール誘導体、その製造方法及び該化合物を含む組成物 | |
| JPH02140A (ja) | カルボン酸ｎ‐オキシ‐アミドおよびヒドロキシルアミン誘導体 | |
| JPS6310749A (ja) | Ｎ−ベンジル２−（４−フルオル−３−トリフルオルメチルフエノキシ）ブタン酸アミド及びそれを含有する除草剤 | |
| DE4238125A1 (de) | Substituierte Triazolinone | |
| CN1207099A (zh) | 取代的磺酰胺基(硫代)羰基化合物 | |
| EP0310558A2 (de) | Mikrobizide Mittel | |
| JPH0399059A (ja) | ４―アルコキシ‐および４‐（置換された）アミノ‐アリールピロリノン誘導体類 | |
| CN1225638A (zh) | 取代的三唑并吖嗪磺酰胺 | |
| CN1057756C (zh) | 一种除草组合物及其制备方法 | |
| HU198008B (en) | Process for producing n-/3-chloro-4-isopropyl-phenyl/-carboxamide derivatives and herbicide compositions containing them as active components | |
| CN1036370C (zh) | 含2-(2-苯并噁唑基氧)乙酰胺类衍生物的除草剂及其制法 | |
| JPS59196896A (ja) | 塩素化されたホスホリルメチルカルボニル誘導体 | |
| JP3593145B2 (ja) | 除草剤ｎ−（４−フルオルフエニル）−ヘテロアリーロキシアセトアミド | |
| JPH02264770A (ja) | 植物を病気から保護するための組成物 | |
| KR860002107B1 (ko) | α, α-디메틸페닐초산 아닐리드 유도체의 제조방법 | |
| JPH0331277A (ja) | 殺微生物組成物 | |
| CN1043891C (zh) | 氟苯并噻唑氧基乙酰胺及制法和作为除莠剂的用途 | |
| JP2001172270A (ja) | ５−カルボキサニリド−２，４−ビス−トリフルオロメチル−チアゾール | |
| CN1195339A (zh) | 4－硫代氨基甲酰基－1－(3－吡唑基)－吡唑化合物及其作除草剂的用途 | |
| JPS60163891A (ja) | フエノキシプロピオニロキシアルカンホスホネート | |
| JPS6254281B2 (zh) | ||
| JPS6277303A (ja) | トリアゾロ−ピリミジン類に基づく除草剤 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |