SK207490A3 - 1-arylimidazoles, method of preparation thereof, use and agent containing 1-arylimidazoles - Google Patents

Info

Publication number

SK207490A3

SK207490A3 SK2074-90A SK207490A SK207490A3 SK 207490 A3 SK207490 A3 SK 207490A3 SK 207490 A SK207490 A SK 207490A SK 207490 A3 SK207490 A3 SK 207490A3

Authority

SK

Slovakia

Prior art keywords

group

formula

compound

dichloro

trifluoromethylphenyl

Prior art date

1989-05-05

Links

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• 238000000034 method Methods 0.000 title claims abstract description 313
• 238000002360 preparation method Methods 0.000 title claims description 76
• 150000001875 compounds Chemical class 0.000 claims abstract description 638
• -1 methylsulfenyl Chemical group 0.000 claims abstract description 164
• 239000000203 mixture Substances 0.000 claims abstract description 117
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 96
• 125000005843 halogen group Chemical group 0.000 claims abstract description 78
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 69
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 69
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 64
• 239000001257 hydrogen Substances 0.000 claims abstract description 63
• 230000008569 process Effects 0.000 claims abstract description 60
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 51
• 241000238421 Arthropoda Species 0.000 claims abstract description 39
• 125000004647 alkyl sulfenyl group Chemical group 0.000 claims abstract description 39
• 241000244206 Nematoda Species 0.000 claims abstract description 33
• 125000001424 substituent group Chemical group 0.000 claims abstract description 32
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 31
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 31
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 27
• 241000238876 Acari Species 0.000 claims abstract description 26
• 241000238631 Hexapoda Species 0.000 claims abstract description 20
• 244000000013 helminth Species 0.000 claims abstract description 20
• 241001124076 Aphididae Species 0.000 claims abstract description 13
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims abstract description 6
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims abstract description 5
• 238000006243 chemical reaction Methods 0.000 claims description 148
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 93
• 239000000460 chlorine Substances 0.000 claims description 65
• 229910052736 halogen Inorganic materials 0.000 claims description 48
• 150000003839 salts Chemical class 0.000 claims description 48
• 239000004480 active ingredient Substances 0.000 claims description 44
• 150000002367 halogens Chemical class 0.000 claims description 44
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 42
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 41
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 40
• 125000000304 alkynyl group Chemical group 0.000 claims description 35
• 229910052801 chlorine Inorganic materials 0.000 claims description 35
• 125000003277 amino group Chemical group 0.000 claims description 33
• 150000002431 hydrogen Chemical class 0.000 claims description 31
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 30
• 238000006467 substitution reaction Methods 0.000 claims description 30
• 239000002253 acid Substances 0.000 claims description 28
• 229910052794 bromium Inorganic materials 0.000 claims description 27
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 27
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
• 239000007787 solid Substances 0.000 claims description 25
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
• 239000013543 active substance Substances 0.000 claims description 22
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 22
• 125000004432 carbon atom Chemical group C* 0.000 claims description 22
• 239000003153 chemical reaction reagent Substances 0.000 claims description 22
• 239000003795 chemical substances by application Substances 0.000 claims description 22
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 21
• 239000004615 ingredient Substances 0.000 claims description 20
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 19
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
• 125000003282 alkyl amino group Chemical group 0.000 claims description 18
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
• 125000003342 alkenyl group Chemical group 0.000 claims description 17
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 17
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 16
• 229910052751 metal Inorganic materials 0.000 claims description 16
• 239000002184 metal Substances 0.000 claims description 16
• 150000003254 radicals Chemical class 0.000 claims description 16
• 239000007788 liquid Substances 0.000 claims description 15
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 14
• 239000003638 chemical reducing agent Substances 0.000 claims description 14
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 13
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 13
• BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 12
• 238000005804 alkylation reaction Methods 0.000 claims description 12
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 12
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
• 125000005265 dialkylamine group Chemical group 0.000 claims description 12
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 12
• 150000004820 halides Chemical class 0.000 claims description 12
• 238000007254 oxidation reaction Methods 0.000 claims description 12
• 150000003973 alkyl amines Chemical class 0.000 claims description 11
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 11
• 239000002168 alkylating agent Substances 0.000 claims description 11
• 229940100198 alkylating agent Drugs 0.000 claims description 11
• 230000029936 alkylation Effects 0.000 claims description 11
• 125000005208 trialkylammonium group Chemical group 0.000 claims description 11
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 10
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 10
• 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 10
• 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 10
• 230000002140 halogenating effect Effects 0.000 claims description 10
• 230000003647 oxidation Effects 0.000 claims description 10
• 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 10
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 9
• 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 9
• 229910021529 ammonia Inorganic materials 0.000 claims description 9
• 239000007800 oxidant agent Substances 0.000 claims description 9
• 150000003457 sulfones Chemical class 0.000 claims description 9
• 150000003462 sulfoxides Chemical class 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 125000004970 halomethyl group Chemical group 0.000 claims description 8
• 239000004094 surface-active agent Substances 0.000 claims description 8
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
• ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 7
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 7
• 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims description 7
• 239000011593 sulfur Substances 0.000 claims description 7
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 7
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
• 239000007818 Grignard reagent Substances 0.000 claims description 6
• 238000007239 Wittig reaction Methods 0.000 claims description 6
• 150000001989 diazonium salts Chemical class 0.000 claims description 6
• 150000004795 grignard reagents Chemical class 0.000 claims description 6
• ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 6
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
• 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 6
• 125000004429 atom Chemical group 0.000 claims description 5
• 239000000969 carrier Substances 0.000 claims description 5
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
• GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• QJNPMBJPNNMBAT-UHFFFAOYSA-N 2-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfanyl)imidazole Chemical compound ClC1=NC(SC(F)(F)F)=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl QJNPMBJPNNMBAT-UHFFFAOYSA-N 0.000 claims description 4
• URCLXLVQHAJFSJ-UHFFFAOYSA-N chlorosulfonyl hypochlorite Chemical compound ClOS(Cl)(=O)=O URCLXLVQHAJFSJ-UHFFFAOYSA-N 0.000 claims description 4
• 239000012954 diazonium Substances 0.000 claims description 4
• 125000001979 organolithium group Chemical group 0.000 claims description 4
• 230000002829 reductive effect Effects 0.000 claims description 4
• 238000006485 reductive methylation reaction Methods 0.000 claims description 4
• 125000000858 thiocyanato group Chemical group *SC#N 0.000 claims description 4
• FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 claims description 3
• WIBROJGYJNSXCM-UHFFFAOYSA-N 4-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(difluoromethylsulfanyl)-2-methylimidazole Chemical compound CC1=NC(Cl)=C(SC(F)F)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl WIBROJGYJNSXCM-UHFFFAOYSA-N 0.000 claims description 3
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
• 230000009471 action Effects 0.000 claims description 3
• 125000001246 bromo group Chemical group Br* 0.000 claims description 3
• 239000012039 electrophile Substances 0.000 claims description 3
• 239000011737 fluorine Substances 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 3
• 239000003999 initiator Substances 0.000 claims description 3
• 239000000276 potassium ferrocyanide Substances 0.000 claims description 3
• XOGGUFAVLNCTRS-UHFFFAOYSA-N tetrapotassium;iron(2+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] XOGGUFAVLNCTRS-UHFFFAOYSA-N 0.000 claims description 3
• XXPDTVUEVHTVPW-UHFFFAOYSA-N 2-bromo-4-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(difluoromethylsulfonyl)imidazole Chemical compound FC(F)S(=O)(=O)C1=C(Cl)N=C(Br)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl XXPDTVUEVHTVPW-UHFFFAOYSA-N 0.000 claims description 2
• SDDIHPXDXRINNN-UHFFFAOYSA-N 2-bromo-4-chloro-1-[2-chloro-6-methylsulfanyl-4-(trifluoromethyl)phenyl]-5-(difluoromethylsulfonyl)imidazole Chemical compound CSC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(S(=O)(=O)C(F)F)=C(Cl)N=C1Br SDDIHPXDXRINNN-UHFFFAOYSA-N 0.000 claims description 2
• JWCRZLABUKAQDI-UHFFFAOYSA-N 2-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)imidazole Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Cl)=NC(S(=O)C(F)(F)F)=C1 JWCRZLABUKAQDI-UHFFFAOYSA-N 0.000 claims description 2
• LFPYUAPDBGDNMS-UHFFFAOYSA-N 2-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfonyl)imidazole Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Cl)=NC(S(=O)(=O)C(F)(F)F)=C1 LFPYUAPDBGDNMS-UHFFFAOYSA-N 0.000 claims description 2
• LRBYJYUIZZFMGK-UHFFFAOYSA-N 2-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-methylsulfanyl-4-(trifluoromethylsulfanyl)imidazole Chemical compound CSC1=C(SC(F)(F)F)N=C(Cl)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl LRBYJYUIZZFMGK-UHFFFAOYSA-N 0.000 claims description 2
• QLYFQPVGLWPCLP-UHFFFAOYSA-N 5-bromo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfanyl)imidazole Chemical compound BrC1=C(SC(F)(F)F)N=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl QLYFQPVGLWPCLP-UHFFFAOYSA-N 0.000 claims description 2
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
• 229910052802 copper Inorganic materials 0.000 claims description 2
• 239000010949 copper Substances 0.000 claims description 2
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
• 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 2
• 230000002147 killing effect Effects 0.000 claims description 2
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
• GQSYDZVWIDZNKM-UHFFFAOYSA-N 2,4-dichloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(difluoromethylsulfonyl)imidazole Chemical compound FC(F)S(=O)(=O)C1=C(Cl)N=C(Cl)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl GQSYDZVWIDZNKM-UHFFFAOYSA-N 0.000 claims 2
• KDGPCOZJZVNTER-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)imidazole Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C=C(S(=O)C(F)(F)F)N=C1 KDGPCOZJZVNTER-UHFFFAOYSA-N 0.000 claims 1
• JRUBJXOHSRRNAZ-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfonyl)imidazole Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C=C(S(=O)(=O)C(F)(F)F)N=C1 JRUBJXOHSRRNAZ-UHFFFAOYSA-N 0.000 claims 1
• JGWYOVNMUXQVAM-UHFFFAOYSA-N 1-[2-chloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)imidazole Chemical compound ClC1=CC(C(F)(F)F)=CC=C1N1C=C(S(=O)C(F)(F)F)N=C1 JGWYOVNMUXQVAM-UHFFFAOYSA-N 0.000 claims 1
• GUDMAJDPKLZYAV-UHFFFAOYSA-N 1-[2-chloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfonyl)imidazole Chemical compound ClC1=CC(C(F)(F)F)=CC=C1N1C=C(S(=O)(=O)C(F)(F)F)N=C1 GUDMAJDPKLZYAV-UHFFFAOYSA-N 0.000 claims 1
• VHSAPFAXZLUADN-UHFFFAOYSA-N 2,4-dichloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(difluoromethylsulfinyl)imidazole Chemical compound FC(F)S(=O)C1=C(Cl)N=C(Cl)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl VHSAPFAXZLUADN-UHFFFAOYSA-N 0.000 claims 1
• VMGGJHIAITUGNO-UHFFFAOYSA-N 2-bromo-4-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(difluoromethylsulfanyl)imidazole Chemical compound FC(F)SC1=C(Cl)N=C(Br)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl VMGGJHIAITUGNO-UHFFFAOYSA-N 0.000 claims 1
• HYHGFMFXOYOBSK-UHFFFAOYSA-N 4-chloro-1-[2,6-dichloro-4-(trifluoromethoxy)phenyl]-2-(difluoromethylsulfanyl)imidazole Chemical compound FC(F)SC1=NC(Cl)=CN1C1=C(Cl)C=C(OC(F)(F)F)C=C1Cl HYHGFMFXOYOBSK-UHFFFAOYSA-N 0.000 claims 1
• QGVPUPHCWVOSRT-UHFFFAOYSA-N 4-chloro-1-[2,6-dichloro-4-(trifluoromethoxy)phenyl]-2-(difluoromethylsulfinyl)imidazole Chemical compound FC(F)S(=O)C1=NC(Cl)=CN1C1=C(Cl)C=C(OC(F)(F)F)C=C1Cl QGVPUPHCWVOSRT-UHFFFAOYSA-N 0.000 claims 1
• YZIQREWRAOHAJZ-UHFFFAOYSA-N 4-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-2-(difluoromethylsulfanyl)imidazole Chemical compound FC(F)SC1=NC(Cl)=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl YZIQREWRAOHAJZ-UHFFFAOYSA-N 0.000 claims 1
• NEODDSWATAOBNN-UHFFFAOYSA-N 4-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-2-(difluoromethylsulfinyl)imidazole Chemical compound FC(F)S(=O)C1=NC(Cl)=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl NEODDSWATAOBNN-UHFFFAOYSA-N 0.000 claims 1
• IUZQCJBLQLBAFV-UHFFFAOYSA-N 4-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(difluoromethylsulfinyl)-2-methylimidazole Chemical compound CC1=NC(Cl)=C(S(=O)C(F)F)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl IUZQCJBLQLBAFV-UHFFFAOYSA-N 0.000 claims 1
• PUNKUTAIOUSCKM-UHFFFAOYSA-N 4-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(difluoromethylsulfonyl)-2-methylimidazole Chemical compound CC1=NC(Cl)=C(S(=O)(=O)C(F)F)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl PUNKUTAIOUSCKM-UHFFFAOYSA-N 0.000 claims 1
• XSESJGXGZNHROO-UHFFFAOYSA-N 4-chloro-2-(difluoromethylsulfanyl)-1-(2,4,6-trichlorophenyl)imidazole Chemical compound FC(F)SC1=NC(Cl)=CN1C1=C(Cl)C=C(Cl)C=C1Cl XSESJGXGZNHROO-UHFFFAOYSA-N 0.000 claims 1
• ZGLZGTWAXJVSNT-UHFFFAOYSA-N 4-chloro-2-(difluoromethylsulfinyl)-1-(2,4,6-trichlorophenyl)imidazole Chemical compound FC(F)S(=O)C1=NC(Cl)=CN1C1=C(Cl)C=C(Cl)C=C1Cl ZGLZGTWAXJVSNT-UHFFFAOYSA-N 0.000 claims 1
• ZDQLRBIHZJOBBQ-UHFFFAOYSA-N 5-bromo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfonyl)imidazole Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Br)=C(S(=O)(=O)C(F)(F)F)N=C1 ZDQLRBIHZJOBBQ-UHFFFAOYSA-N 0.000 claims 1
• NTZPORLFQUHBDG-UHFFFAOYSA-N 5-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfanyl)imidazole Chemical compound ClC1=C(SC(F)(F)F)N=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl NTZPORLFQUHBDG-UHFFFAOYSA-N 0.000 claims 1
• 230000009418 agronomic effect Effects 0.000 claims 1
• 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims 1
• 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
• 150000002823 nitrates Chemical class 0.000 claims 1
• 108090000623 proteins and genes Proteins 0.000 claims 1
• 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
• 239000000543 intermediate Substances 0.000 abstract description 102
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 abstract description 2
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 126
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• 239000002904 solvent Substances 0.000 description 66
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• 238000012360 testing method Methods 0.000 description 63
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 54
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 54
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
• 241000607479 Yersinia pestis Species 0.000 description 50
• 241000196324 Embryophyta Species 0.000 description 47
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
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• 239000000243 solution Substances 0.000 description 39
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 37
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
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• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
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