JPS6130670B2 - - Google Patents

Info

Publication number

JPS6130670B2

JPS6130670B2 JP4075982A JP4075982A JPS6130670B2 JP S6130670 B2 JPS6130670 B2 JP S6130670B2 JP 4075982 A JP4075982 A JP 4075982A JP 4075982 A JP4075982 A JP 4075982A JP S6130670 B2 JPS6130670 B2 JP S6130670B2

Authority

JP

Japan

Prior art keywords

formula

methoxy

compound

atom

present

Prior art date

1982-03-17

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.)

Expired

Links

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• Global Dossier
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• 239000004009 herbicide Substances 0.000 claims description 23
• 230000002363 herbicidal effect Effects 0.000 claims description 19
• -1 N- (6-methoxy-2-pyridyl)-N-methylcarbamoyl halide Chemical class 0.000 claims description 12
• 239000004480 active ingredient Substances 0.000 claims description 8
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 125000004434 sulfur atom Chemical group 0.000 claims description 8
• GXHQLRBOZRJHPZ-UHFFFAOYSA-N 6-methoxy-n-methylpyridin-2-amine Chemical compound CNC1=CC=CC(OC)=N1 GXHQLRBOZRJHPZ-UHFFFAOYSA-N 0.000 claims description 7
• AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 239000007810 chemical reaction solvent Substances 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 3
• JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims 2
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 2
• 229950011260 betanaphthol Drugs 0.000 claims 1
• 150000004820 halides Chemical class 0.000 claims 1
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
• 150000001875 compounds Chemical class 0.000 description 30
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
• 239000002689 soil Substances 0.000 description 16
• 238000012360 testing method Methods 0.000 description 12
• 241000196324 Embryophyta Species 0.000 description 11
• 239000000203 mixture Substances 0.000 description 11
• 241000209094 Oryza Species 0.000 description 10
• 235000007164 Oryza sativa Nutrition 0.000 description 10
• 235000009566 rice Nutrition 0.000 description 10
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 239000003795 chemical substances by application Substances 0.000 description 9
• 230000000694 effects Effects 0.000 description 9
• 238000006243 chemical reaction Methods 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 239000000126 substance Substances 0.000 description 8
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• 244000025254 Cannabis sativa Species 0.000 description 6
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• 238000009472 formulation Methods 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• 244000068988 Glycine max Species 0.000 description 5
• 235000010469 Glycine max Nutrition 0.000 description 5
• 238000009333 weeding Methods 0.000 description 5
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
• 230000000887 hydrating effect Effects 0.000 description 4
• 229910052573 porcelain Inorganic materials 0.000 description 4
• 229910000027 potassium carbonate Inorganic materials 0.000 description 4
• 235000011181 potassium carbonates Nutrition 0.000 description 4
• 239000011541 reaction mixture Substances 0.000 description 4
• 239000004094 surface-active agent Substances 0.000 description 4
• 229920000742 Cotton Polymers 0.000 description 3
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 241001148683 Zostera marina Species 0.000 description 3
• 239000000839 emulsion Substances 0.000 description 3
• 239000008187 granular material Substances 0.000 description 3
• 238000010992 reflux Methods 0.000 description 3
• 239000007787 solid Substances 0.000 description 3
• 239000004563 wettable powder Substances 0.000 description 3
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
• 239000003905 agrochemical Substances 0.000 description 2
• 239000000440 bentonite Substances 0.000 description 2
• 229910000278 bentonite Inorganic materials 0.000 description 2
• SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
• 230000015572 biosynthetic process Effects 0.000 description 2
• 239000000969 carrier Substances 0.000 description 2
• 238000004440 column chromatography Methods 0.000 description 2
• 239000013078 crystal Substances 0.000 description 2
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-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
• 238000011156 evaluation Methods 0.000 description 2
• KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 2
• 239000010410 layer Substances 0.000 description 2
• 238000002844 melting Methods 0.000 description 2
• 230000008018 melting Effects 0.000 description 2
• 238000000034 method Methods 0.000 description 2
• 238000002156 mixing Methods 0.000 description 2
• 239000000843 powder Substances 0.000 description 2
• 239000002994 raw material Substances 0.000 description 2
• 229920006395 saturated elastomer Polymers 0.000 description 2
• 239000000741 silica gel Substances 0.000 description 2
• 229910002027 silica gel Inorganic materials 0.000 description 2
• 239000011780 sodium chloride Substances 0.000 description 2
• 238000009331 sowing Methods 0.000 description 2
• 238000003786 synthesis reaction Methods 0.000 description 2
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
• 238000005292 vacuum distillation Methods 0.000 description 2
• QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
• 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
• UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 1
• VAVGOGHLNAJECD-UHFFFAOYSA-N 2-chloro-6-methoxypyridine Chemical compound COC1=CC=CC(Cl)=N1 VAVGOGHLNAJECD-UHFFFAOYSA-N 0.000 description 1
• LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 1
• 241000254032 Acrididae 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
• 240000001592 Amaranthus caudatus Species 0.000 description 1
• 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
• 239000005476 Bentazone Substances 0.000 description 1
• 235000006890 Chamerion angustifolium subsp angustifolium Nutrition 0.000 description 1
• 235000002278 Chamerion angustifolium subsp circumvagum Nutrition 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• 244000287353 Crassocephalum crepidioides Species 0.000 description 1
• 244000301850 Cupressus sempervirens Species 0.000 description 1
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
• 241000219146 Gossypium Species 0.000 description 1
• 239000005909 Kieselgur Substances 0.000 description 1
• 241000254158 Lampyridae Species 0.000 description 1
• 239000005573 Linuron Substances 0.000 description 1
• 239000005575 MCPB Substances 0.000 description 1
• 101150039283 MCPB gene Proteins 0.000 description 1
• 241001502127 Mullus barbatus Species 0.000 description 1
• JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
• LVKTWOXHRYGDMM-UHFFFAOYSA-N Naproanilide Chemical compound C=1C=C2C=CC=CC2=CC=1OC(C)C(=O)NC1=CC=CC=C1 LVKTWOXHRYGDMM-UHFFFAOYSA-N 0.000 description 1
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
• CHNUNORXWHYHNE-UHFFFAOYSA-N Oxadiazon Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(OC(=N2)C(C)(C)C)=O)=C1Cl CHNUNORXWHYHNE-UHFFFAOYSA-N 0.000 description 1
• 241001076438 Oxya japonica Species 0.000 description 1
• 231100000674 Phytotoxicity Toxicity 0.000 description 1
• 241001092459 Rubus Species 0.000 description 1
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
• 241000219793 Trifolium Species 0.000 description 1
• XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
• 150000001408 amides Chemical class 0.000 description 1
• 150000004945 aromatic hydrocarbons 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
• 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
• 238000009835 boiling Methods 0.000 description 1
• HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 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
• 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
• 239000012876 carrier material Substances 0.000 description 1
• 239000000460 chlorine Substances 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 239000004927 clay Substances 0.000 description 1
• 235000012343 cottonseed oil Nutrition 0.000 description 1
• 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
• HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 229940079593 drug Drugs 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 238000000921 elemental analysis Methods 0.000 description 1
• 239000012259 ether extract Substances 0.000 description 1
• 150000002170 ethers Chemical class 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 239000003337 fertilizer Substances 0.000 description 1
• 239000000417 fungicide Substances 0.000 description 1
• 230000035784 germination Effects 0.000 description 1
• 239000003630 growth substance Substances 0.000 description 1
• 150000008282 halocarbons Chemical class 0.000 description 1
• 125000000623 heterocyclic group Chemical group 0.000 description 1
• 150000004679 hydroxides Chemical class 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 239000002917 insecticide Substances 0.000 description 1
• 238000011835 investigation Methods 0.000 description 1
• 239000003350 kerosene Substances 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 229910052753 mercury Inorganic materials 0.000 description 1
• 229910052987 metal hydride Inorganic materials 0.000 description 1
• 150000004681 metal hydrides Chemical class 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
• ONJLWIHTFJQMQI-UHFFFAOYSA-N n-(6-methoxypyridin-2-yl)-n-methylcarbamothioyl chloride Chemical compound COC1=CC=CC(N(C)C(Cl)=S)=N1 ONJLWIHTFJQMQI-UHFFFAOYSA-N 0.000 description 1
• UWCQEUPIPXEYFL-UHFFFAOYSA-N n-(6-methoxypyridin-2-yl)-n-methylcarbamoyl chloride Chemical compound COC1=CC=CC(N(C)C(Cl)=O)=N1 UWCQEUPIPXEYFL-UHFFFAOYSA-N 0.000 description 1
• SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical compound CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 description 1
• RMBCQVQFRYIMFN-UHFFFAOYSA-N naphthalen-1-yl carbamate Chemical class C1=CC=C2C(OC(=O)N)=CC=CC2=C1 RMBCQVQFRYIMFN-UHFFFAOYSA-N 0.000 description 1
• QMTSVCGZJDUPJQ-UHFFFAOYSA-N naphthalen-2-yl n-(6-methoxypyridin-2-yl)-n-methylcarbamate Chemical compound COC1=CC=CC(N(C)C(=O)OC=2C=C3C=CC=CC3=CC=2)=N1 QMTSVCGZJDUPJQ-UHFFFAOYSA-N 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• INFPIPCTRVDPJG-UHFFFAOYSA-N o-naphthalen-2-yl chloromethanethioate Chemical compound C1=CC=CC2=CC(OC(=S)Cl)=CC=C21 INFPIPCTRVDPJG-UHFFFAOYSA-N 0.000 description 1
• LMQJRYKENGECRN-UHFFFAOYSA-N o-naphthalen-2-yl n-(6-methoxypyridin-2-yl)-n-methylcarbamothioate Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C3C=CC=CC3=CC=2)=N1 LMQJRYKENGECRN-UHFFFAOYSA-N 0.000 description 1
• 239000013459 phenoxy herbicide Substances 0.000 description 1
• 239000002798 polar solvent Substances 0.000 description 1
• 239000011736 potassium bicarbonate Substances 0.000 description 1
• 235000015497 potassium bicarbonate Nutrition 0.000 description 1
• 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
• 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
• LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
• 238000010298 pulverizing process Methods 0.000 description 1
• ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 230000035484 reaction time Effects 0.000 description 1
• 238000011160 research Methods 0.000 description 1
• ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
• MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 235000017550 sodium carbonate Nutrition 0.000 description 1
• 239000012312 sodium hydride Substances 0.000 description 1
• 229910000104 sodium hydride Inorganic materials 0.000 description 1
• 238000005507 spraying Methods 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 239000002344 surface layer Substances 0.000 description 1
• 238000004381 surface treatment Methods 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
• ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
• 239000008096 xylene Substances 0.000 description 1