HU192164B - Herbicides containing n-phenyl-pyrazle derviatives and process for preparing the active substances - Google Patents

Info

Publication number

HU192164B

HU192164B HU832507A HU250783A HU192164B HU 192164 B HU192164 B HU 192164B HU 832507 A HU832507 A HU 832507A HU 250783 A HU250783 A HU 250783A HU 192164 B HU192164 B HU 192164B

Authority

HU

Hungary

Prior art keywords

pyrazole

cyano

phenyl

trifluoromethyl

formula

Prior art date

1982-07-15

Links

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• 239000004009 herbicide Substances 0.000 title claims description 66
• 239000013543 active substance Substances 0.000 title description 4
• 238000004519 manufacturing process Methods 0.000 title description 2
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 222
• 150000001875 compounds Chemical class 0.000 claims description 216
• -1 2-oxoazetidin-1-yl Chemical group 0.000 claims description 212
• 239000007787 solid Substances 0.000 claims description 110
• 239000000203 mixture Substances 0.000 claims description 95
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 88
• 125000000217 alkyl group Chemical group 0.000 claims description 82
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 72
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 72
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 68
• 239000011541 reaction mixture Substances 0.000 claims description 68
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 60
• 238000010992 reflux Methods 0.000 claims description 56
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 55
• 239000001257 hydrogen Substances 0.000 claims description 49
• 229910052739 hydrogen Inorganic materials 0.000 claims description 49
• 238000000034 method Methods 0.000 claims description 48
• 238000006243 chemical reaction Methods 0.000 claims description 37
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 36
• 230000002363 herbicidal effect Effects 0.000 claims description 36
• 238000002360 preparation method Methods 0.000 claims description 36
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
• 239000007788 liquid Substances 0.000 claims description 35
• 239000003960 organic solvent Substances 0.000 claims description 31
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 26
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 25
• 229910052783 alkali metal Inorganic materials 0.000 claims description 25
• 125000003545 alkoxy group Chemical group 0.000 claims description 25
• 150000001340 alkali metals Chemical class 0.000 claims description 23
• 239000004563 wettable powder Substances 0.000 claims description 23
• 239000004094 surface-active agent Substances 0.000 claims description 22
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 20
• 239000003085 diluting agent Substances 0.000 claims description 19
• 125000004432 carbon atom Chemical group C* 0.000 claims description 18
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 17
• 239000004480 active ingredient Substances 0.000 claims description 17
• 125000003277 amino group Chemical group 0.000 claims description 17
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 17
• WITMXBRCQWOZPX-UHFFFAOYSA-N 1-phenylpyrazole Chemical class C1=CC=NN1C1=CC=CC=C1 WITMXBRCQWOZPX-UHFFFAOYSA-N 0.000 claims description 16
• 239000012141 concentrate Substances 0.000 claims description 16
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
• NEURYOYRKPFLKH-UHFFFAOYSA-N 2-chloro-1-isocyanato-4-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC=C(N=C=O)C(Cl)=C1 NEURYOYRKPFLKH-UHFFFAOYSA-N 0.000 claims description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
• 239000002253 acid Substances 0.000 claims description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
• 239000000843 powder Substances 0.000 claims description 15
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
• LEDRYVPMZZWKGC-UHFFFAOYSA-N 5-(ethylamino)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical group CCNC1=C(C#N)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl LEDRYVPMZZWKGC-UHFFFAOYSA-N 0.000 claims description 13
• 229910052801 chlorine Inorganic materials 0.000 claims description 13
• OXGMPHJRFSDDLO-UHFFFAOYSA-N 5-(2-oxopyrrolidin-1-yl)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical group ClC1=C(Cl)C(Cl)=CC=C1N1C(N2C(CCC2)=O)=C(C#N)C=N1 OXGMPHJRFSDDLO-UHFFFAOYSA-N 0.000 claims description 12
• 125000005265 dialkylamine group Chemical group 0.000 claims description 12
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 11
• 239000000460 chlorine Substances 0.000 claims description 11
• 239000004550 soluble concentrate Substances 0.000 claims description 11
• 239000004546 suspension concentrate Substances 0.000 claims description 11
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 229910000027 potassium carbonate Inorganic materials 0.000 claims description 10
• 235000011181 potassium carbonates Nutrition 0.000 claims description 10
• 239000002904 solvent Substances 0.000 claims description 10
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
• 239000002585 base Substances 0.000 claims description 9
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
• 239000002562 thickening agent Substances 0.000 claims description 9
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 8
• 239000007900 aqueous suspension Substances 0.000 claims description 8
• 229910000104 sodium hydride Inorganic materials 0.000 claims description 8
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 7
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
• 229910052794 bromium Inorganic materials 0.000 claims description 7
• 239000004495 emulsifiable concentrate Substances 0.000 claims description 7
• 150000003217 pyrazoles Chemical class 0.000 claims description 7
• 239000012312 sodium hydride Substances 0.000 claims description 7
• XSQRNLNKJBNDQJ-UHFFFAOYSA-N 5-(2-methyl-4-oxoazetidin-1-yl)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound CC1CC(=O)N1C1=C(C#N)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl XSQRNLNKJBNDQJ-UHFFFAOYSA-N 0.000 claims description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
• 125000000033 alkoxyamino group Chemical group 0.000 claims description 6
• 125000002947 alkylene group Chemical group 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 239000011737 fluorine Substances 0.000 claims description 6
• QCSVQOBDDQLEHF-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(2-oxoazetidin-1-yl)pyrazole-4-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(N2C(CC2)=O)=C(C#N)C=N1 QCSVQOBDDQLEHF-UHFFFAOYSA-N 0.000 claims description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• JJLKTTCRRLHVGL-UHFFFAOYSA-L [acetyloxy(dibutyl)stannyl] acetate Chemical group CC([O-])=O.CC([O-])=O.CCCC[Sn+2]CCCC JJLKTTCRRLHVGL-UHFFFAOYSA-L 0.000 claims description 5
• 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• 150000002431 hydrogen Chemical class 0.000 claims description 5
• 230000007062 hydrolysis Effects 0.000 claims description 5
• 238000006460 hydrolysis reaction Methods 0.000 claims description 5
• DSCFTPNPDGOAFW-UHFFFAOYSA-N methyl 2-[[2-[2-chloro-4-(trifluoromethyl)phenyl]-4-cyanopyrazol-3-yl]amino]acetate Chemical compound COC(=O)CNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl DSCFTPNPDGOAFW-UHFFFAOYSA-N 0.000 claims description 5
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
• 125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 235000015497 potassium bicarbonate Nutrition 0.000 claims description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• UUSUPPWMXHZANT-UHFFFAOYSA-N 1-[2-chloro-4-(trifluoromethyl)phenyl]-5-(2-oxopyrrolidin-1-yl)pyrazole-4-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC=C1N1C(N2C(CCC2)=O)=C(C#N)C=N1 UUSUPPWMXHZANT-UHFFFAOYSA-N 0.000 claims description 4
• FTHMYEFVAPBKRU-UHFFFAOYSA-N 5-(methylamino)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound CNC1=C(C#N)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl FTHMYEFVAPBKRU-UHFFFAOYSA-N 0.000 claims description 4
• ALZAFERETJSZHP-UHFFFAOYSA-N 5-(propan-2-ylamino)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound CC(C)NC1=C(C#N)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl ALZAFERETJSZHP-UHFFFAOYSA-N 0.000 claims description 4
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
• 150000004703 alkoxides Chemical class 0.000 claims description 4
• 229910021529 ammonia Inorganic materials 0.000 claims description 4
• 239000007864 aqueous solution Substances 0.000 claims description 4
• NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 claims description 4
• 125000001246 bromo group Chemical group Br* 0.000 claims description 4
• 150000003983 crown ethers Chemical class 0.000 claims description 4
• 239000003995 emulsifying agent Substances 0.000 claims description 4
• LQQCPHZSKNCUMD-UHFFFAOYSA-N ethyl n-[4-cyano-2-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazol-3-yl]methanimidate Chemical compound CCOC=NC1=C(C#N)C=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl LQQCPHZSKNCUMD-UHFFFAOYSA-N 0.000 claims description 4
• 239000011777 magnesium Substances 0.000 claims description 4
• 229910052749 magnesium Inorganic materials 0.000 claims description 4
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
• 150000007522 mineralic acids Chemical class 0.000 claims description 4
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 239000000377 silicon dioxide Substances 0.000 claims description 4
• 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
• 239000012279 sodium borohydride Substances 0.000 claims description 4
• WXPNQEITSSNOQB-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-(ethylamino)pyrazole-4-carbonitrile Chemical compound CCNC1=C(C#N)C=NN1C1=CC=C(Cl)C=C1Cl WXPNQEITSSNOQB-UHFFFAOYSA-N 0.000 claims description 3
• XPPNPRYYOXLRRZ-UHFFFAOYSA-N 1-(4-chloro-2,3,5,6-tetrafluorophenyl)-5-(2-methyl-4-oxoazetidin-1-yl)pyrazole-4-carbonitrile Chemical compound CC1CC(=O)N1C1=C(C#N)C=NN1C1=C(F)C(F)=C(Cl)C(F)=C1F XPPNPRYYOXLRRZ-UHFFFAOYSA-N 0.000 claims description 3
• BVIMNUKIJANOBI-UHFFFAOYSA-N 1-(4-ethyl-2,3,5,6-tetrafluorophenyl)-5-(2-oxoazetidin-1-yl)pyrazole-4-carbonitrile Chemical compound FC1=C(F)C(CC)=C(F)C(F)=C1N1C(N2C(CC2)=O)=C(C#N)C=N1 BVIMNUKIJANOBI-UHFFFAOYSA-N 0.000 claims description 3
• SPOSAXFNVLKYBU-UHFFFAOYSA-N 1-(4-ethyl-2,3,5,6-tetrafluorophenyl)-5-(methylamino)pyrazole-4-carbonitrile Chemical compound FC1=C(F)C(CC)=C(F)C(F)=C1N1C(NC)=C(C#N)C=N1 SPOSAXFNVLKYBU-UHFFFAOYSA-N 0.000 claims description 3
• ZYUGQEXSHMDOSO-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(methylamino)pyrazole-4-carbonitrile Chemical compound CNC1=C(C#N)C=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZYUGQEXSHMDOSO-UHFFFAOYSA-N 0.000 claims description 3
• QQVKZCVQPSCMHF-UHFFFAOYSA-N 1-[2-chloro-4-(trifluoromethyl)phenyl]-5-(2-methylpropylamino)pyrazole-4-carbonitrile Chemical compound CC(C)CNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl QQVKZCVQPSCMHF-UHFFFAOYSA-N 0.000 claims description 3
• HMKSNBGLIUYMRJ-UHFFFAOYSA-N 1-[2-chloro-4-(trifluoromethyl)phenyl]-5-(ethylamino)pyrazole-4-carbonitrile Chemical compound CCNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl HMKSNBGLIUYMRJ-UHFFFAOYSA-N 0.000 claims description 3
• BMEDIMBUAQKCOV-UHFFFAOYSA-N 1-[2-chloro-4-(trifluoromethyl)phenyl]-5-(propan-2-ylamino)pyrazole-4-carbonitrile Chemical compound CC(C)NC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl BMEDIMBUAQKCOV-UHFFFAOYSA-N 0.000 claims description 3
• LCUPJRJRHZYESP-UHFFFAOYSA-N 1-[2-chloro-4-(trifluoromethyl)phenyl]-5-(propylamino)pyrazole-4-carbonitrile Chemical compound CCCNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl LCUPJRJRHZYESP-UHFFFAOYSA-N 0.000 claims description 3
• XRMWZSOKBCRUMR-UHFFFAOYSA-N 1-[2-chloro-4-(trifluoromethyl)phenyl]-5-(propylsulfanylamino)pyrazole-4-carbonitrile Chemical compound CCCSNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl XRMWZSOKBCRUMR-UHFFFAOYSA-N 0.000 claims description 3
• HTUPAPXJKGSIFU-UHFFFAOYSA-N 1-[2-chloro-4-(trifluoromethyl)phenyl]-5-[(2-morpholin-4-yl-2-oxoethyl)amino]pyrazole-4-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC=C1N1C(NCC(=O)N2CCOCC2)=C(C#N)C=N1 HTUPAPXJKGSIFU-UHFFFAOYSA-N 0.000 claims description 3
• TVFWYUWNQVRQRG-UHFFFAOYSA-N 2,3,4-tris(2-phenylethenyl)phenol Chemical compound C=1C=CC=CC=1C=CC1=C(C=CC=2C=CC=CC=2)C(O)=CC=C1C=CC1=CC=CC=C1 TVFWYUWNQVRQRG-UHFFFAOYSA-N 0.000 claims description 3
• RPVVPWGPAXLXQD-UHFFFAOYSA-N 3-[[2-[2-chloro-4-(trifluoromethyl)phenyl]-4-cyanopyrazol-3-yl]amino]propanoic acid Chemical compound OC(=O)CCNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl RPVVPWGPAXLXQD-UHFFFAOYSA-N 0.000 claims description 3
• XHIGETXERJGTON-UHFFFAOYSA-N 3-[[4-cyano-2-(4-ethyl-2,3,5,6-tetrafluorophenyl)pyrazol-3-yl]amino]-2-methylpropanoic acid Chemical compound FC1=C(F)C(CC)=C(F)C(F)=C1N1C(NCC(C)C(O)=O)=C(C#N)C=N1 XHIGETXERJGTON-UHFFFAOYSA-N 0.000 claims description 3
• DIWBOCJTILWPOP-UHFFFAOYSA-N 5-(2,2-dimethyl-4-oxoazetidin-1-yl)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical group CC1(C)CC(=O)N1C1=C(C#N)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl DIWBOCJTILWPOP-UHFFFAOYSA-N 0.000 claims description 3
• JGTZLKSJWQQUCM-UHFFFAOYSA-N 5-(2-hydroxyethylamino)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound OCCNC1=C(C#N)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl JGTZLKSJWQQUCM-UHFFFAOYSA-N 0.000 claims description 3
• RCHFYFBLBPLUGA-UHFFFAOYSA-N 5-(2-oxoazetidin-1-yl)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound ClC1=C(Cl)C(Cl)=CC=C1N1C(N2C(CC2)=O)=C(C#N)C=N1 RCHFYFBLBPLUGA-UHFFFAOYSA-N 0.000 claims description 3
• YNPLRKMTNAJXMQ-UHFFFAOYSA-N 5-(2-oxoazetidin-1-yl)-1-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]pyrazole-4-carbonitrile Chemical compound FC1=C(F)C(C(F)(F)F)=C(F)C(F)=C1N1C(N2C(CC2)=O)=C(C#N)C=N1 YNPLRKMTNAJXMQ-UHFFFAOYSA-N 0.000 claims description 3
• SZLCUKUFHXTSBE-UHFFFAOYSA-N 5-(butan-2-ylamino)-1-[2-chloro-4-(trifluoromethyl)phenyl]pyrazole-4-carbonitrile Chemical compound CCC(C)NC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl SZLCUKUFHXTSBE-UHFFFAOYSA-N 0.000 claims description 3
• NBMYPTDTCKYLCA-UHFFFAOYSA-N 5-(butylamino)-1-[2-chloro-4-(trifluoromethyl)phenyl]pyrazole-4-carbonitrile Chemical compound CCCCNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl NBMYPTDTCKYLCA-UHFFFAOYSA-N 0.000 claims description 3
• DOZLCBWMDPNTNO-UHFFFAOYSA-N 5-(dimethylamino)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound CN(C)C1=C(C#N)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl DOZLCBWMDPNTNO-UHFFFAOYSA-N 0.000 claims description 3
• QXNDHGDFPZVTRB-UHFFFAOYSA-N 5-(dipropylamino)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound CCCN(CCC)C1=C(C#N)C=NN1C1=CC=C(Cl)C(Cl)=C1Cl QXNDHGDFPZVTRB-UHFFFAOYSA-N 0.000 claims description 3
• DHUPEROHCYFCQB-UHFFFAOYSA-N 5-(ethylamino)-1-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]pyrazole-4-carbonitrile Chemical compound CCNC1=C(C#N)C=NN1C1=C(F)C(F)=C(C(F)(F)F)C(F)=C1F DHUPEROHCYFCQB-UHFFFAOYSA-N 0.000 claims description 3
• IETDCPOBPMTKTL-UHFFFAOYSA-N 5-(prop-2-enylamino)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound ClC1=C(Cl)C(Cl)=CC=C1N1C(NCC=C)=C(C#N)C=N1 IETDCPOBPMTKTL-UHFFFAOYSA-N 0.000 claims description 3
• WZLJAZJUHNBEFK-UHFFFAOYSA-N 5-(prop-2-ynylamino)-1-(2,3,4-trichlorophenyl)pyrazole-4-carbonitrile Chemical compound ClC1=C(Cl)C(Cl)=CC=C1N1C(NCC#C)=C(C#N)C=N1 WZLJAZJUHNBEFK-UHFFFAOYSA-N 0.000 claims description 3
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
• GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 3
• 239000002270 dispersing agent Substances 0.000 claims description 3
• YUJLWVKRERGBAS-UHFFFAOYSA-N ethyl 2-[[2-[2-chloro-4-(trifluoromethyl)phenyl]-4-cyanopyrazol-3-yl]amino]acetate Chemical compound CCOC(=O)CNC1=C(C#N)C=NN1C1=CC=C(C(F)(F)F)C=C1Cl YUJLWVKRERGBAS-UHFFFAOYSA-N 0.000 claims description 3
• 150000004676 glycans Chemical class 0.000 claims description 3
• 229910052736 halogen Inorganic materials 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 150000002367 halogens Chemical class 0.000 claims description 3
• 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
• 235000010755 mineral Nutrition 0.000 claims description 3
• 239000002480 mineral oil Substances 0.000 claims description 3
• 229910052901 montmorillonite Inorganic materials 0.000 claims description 3
• 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 3
• 229920001282 polysaccharide Polymers 0.000 claims description 3
• 239000005017 polysaccharide Substances 0.000 claims description 3
• 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 3
• 239000011736 potassium bicarbonate Substances 0.000 claims description 3
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 3
• 239000002516 radical scavenger Substances 0.000 claims description 3
• 159000000000 sodium salts Chemical class 0.000 claims description 3
• 239000000080 wetting agent Substances 0.000 claims description 3
• 239000000230 xanthan gum Substances 0.000 claims description 3
• 229920001285 xanthan gum Polymers 0.000 claims description 3
• 229940082509 xanthan gum Drugs 0.000 claims description 3
• 235000010493 xanthan gum Nutrition 0.000 claims description 3
• HAGJZUCBGIPNOI-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-(2-methyl-4-oxoazetidin-1-yl)pyrazole-4-carbonitrile Chemical compound CC1CC(=O)N1C1=C(C#N)C=NN1C1=CC=C(Cl)C=C1Cl HAGJZUCBGIPNOI-UHFFFAOYSA-N 0.000 claims description 2
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