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

1-arylimidazoles, method of preparation thereof, use and agent containing 1-arylimidazoles Download PDF

Info

Publication number: SK207490A3
Authority: SK; Slovakia
Prior art keywords: group; formula; compound; dichloro; trifluoromethylphenyl
Prior art date: 1989-05-05

Application number

SK2074-90A

Other languages

English (en)

Slovak (sk)

Other versions

SK279264B6 (sk

Inventor

Powell G Scotton

Sinodis D Neal

Timmons P Reid

Tai-Teh Wu

Original Assignee

Rhone Poulenc Agrochimie

Priority date (The priority date 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 date listed.)

1989-05-05

Filing date

1990-04-25

Publication date

1998-08-05

1990-04-25 Application filed by Rhone Poulenc Agrochimie filed Critical Rhone Poulenc Agrochimie

1998-08-05 Publication of SK279264B6 publication Critical patent/SK279264B6/sk

1998-08-05 Publication of SK207490A3 publication Critical patent/SK207490A3/sk

Links

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
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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
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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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238000012360 testing method Methods 0.000 description 63
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
241000607479 Yersinia pestis Species 0.000 description 50
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239000000243 solution Substances 0.000 description 39
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KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
229920005615 natural polymer Polymers 0.000 description 1
150000002825 nitriles Chemical group 0.000 description 1
JCZMXVGQBBATMY-UHFFFAOYSA-N nitro acetate Chemical compound CC(=O)O[N+]([O-])=O JCZMXVGQBBATMY-UHFFFAOYSA-N 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-O nitrosooxidanium Chemical compound [OH2+]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-O 0.000 description 1
HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical compound [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
235000014571 nuts Nutrition 0.000 description 1
229920002113 octoxynol Polymers 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000011368 organic material Substances 0.000 description 1
125000002734 organomagnesium group Chemical group 0.000 description 1
230000001151 other effect Effects 0.000 description 1
230000003151 ovacidal effect Effects 0.000 description 1
230000017448 oviposition Effects 0.000 description 1
KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
239000005022 packaging material Substances 0.000 description 1
238000010422 painting Methods 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
230000003071 parasitic effect Effects 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
239000003415 peat Substances 0.000 description 1
230000000149 penetrating effect Effects 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000003090 pesticide formulation Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
FPISENDBCQYRQB-UHFFFAOYSA-N phenol;phosphoric acid Chemical class OP(O)(O)=O.OC1=CC=CC=C1 FPISENDBCQYRQB-UHFFFAOYSA-N 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
150000004841 phenylimidazoles Chemical class 0.000 description 1
239000003016 pheromone Substances 0.000 description 1
BULVZWIRKLYCBC-UHFFFAOYSA-N phorate Chemical compound CCOP(=S)(OCC)SCSCC BULVZWIRKLYCBC-UHFFFAOYSA-N 0.000 description 1
IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
239000011574 phosphorus Substances 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
230000003032 phytopathogenic effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
QHOQHJPRIBSPCY-UHFFFAOYSA-N pirimiphos-methyl Chemical group CCN(CC)C1=NC(C)=CC(OP(=S)(OC)OC)=N1 QHOQHJPRIBSPCY-UHFFFAOYSA-N 0.000 description 1
238000009372 pisciculture Methods 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920013639 polyalphaolefin Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
239000005077 polysulfide Substances 0.000 description 1
229920001021 polysulfide Polymers 0.000 description 1
150000008117 polysulfides Polymers 0.000 description 1
229920001343 polytetrafluoroethylene Polymers 0.000 description 1
239000004810 polytetrafluoroethylene Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
OKBMCNHOEMXPTM-UHFFFAOYSA-M potassium peroxymonosulfate Chemical compound [K+].OOS([O-])(=O)=O OKBMCNHOEMXPTM-UHFFFAOYSA-M 0.000 description 1
ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
229940116357 potassium thiocyanate Drugs 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
238000003825 pressing Methods 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000008262 pumice Substances 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
239000010453 quartz Substances 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000003340 retarding agent Substances 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000011435 rock Substances 0.000 description 1
210000004767 rumen Anatomy 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
238000007873 sieving Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
210000000813 small intestine Anatomy 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
229910052911 sodium silicate Inorganic materials 0.000 description 1
235000010339 sodium tetraborate Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000004550 soluble concentrate Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000009987 spinning Methods 0.000 description 1
210000004215 spore Anatomy 0.000 description 1
230000028070 sporulation Effects 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
239000004575 stone Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
230000001629 suppression Effects 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
235000013616 tea Nutrition 0.000 description 1
CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
239000011135 tin Substances 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000004954 trialkylamino group Chemical group 0.000 description 1
AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
229940096911 trichinella spiralis Drugs 0.000 description 1
NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
RQYLOOVORNJDQX-UHFFFAOYSA-N trifluoromethyl thiohypochlorite Chemical compound FC(F)(F)SCl RQYLOOVORNJDQX-UHFFFAOYSA-N 0.000 description 1
AFZDAWIXETXKRE-UHFFFAOYSA-M triphenyl(prop-2-ynyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC#C)C1=CC=CC=C1 AFZDAWIXETXKRE-UHFFFAOYSA-M 0.000 description 1
HHBXWXJLQYJJBW-UHFFFAOYSA-M triphenyl(propan-2-yl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C(C)C)C1=CC=CC=C1 HHBXWXJLQYJJBW-UHFFFAOYSA-M 0.000 description 1
BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
230000035899 viability Effects 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
239000002699 waste material Substances 0.000 description 1
229920003169 water-soluble polymer Polymers 0.000 description 1
238000004018 waxing Methods 0.000 description 1
238000009941 weaving Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/70—One oxygen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/84—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/88—Nitrogen atoms, e.g. allantoin

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Environmental Sciences (AREA)
Wood Science & Technology (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Zoology (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pyrrole Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Professional, Industrial, Or Sporting Protective Garments (AREA)
Detergent Compositions (AREA)
Orthopedics, Nursing, And Contraception (AREA)
Resistance Heating (AREA)
Rigid Pipes And Flexible Pipes (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SK2074-90A 1989-05-05 1990-04-25 1-arylimidazoles, method of preparation thereof, use and agent containing 1-arylimidazoles SK207490A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US34868289A	1989-05-05	1989-05-05

Publications (2)

Publication Number	Publication Date
SK279264B6 SK279264B6 (sk)	1998-08-05
SK207490A3 true SK207490A3 (en)	1998-08-05

Family

ID=23369091

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK2074-90A SK207490A3 (en)	1989-05-05	1990-04-25	1-arylimidazoles, method of preparation thereof, use and agent containing 1-arylimidazoles

Country Status (31)

Country	Link
EP (1)	EP0396427B1 (fr)
JP (1)	JP2943993B2 (fr)
KR (1)	KR0160512B1 (fr)
CN (1)	CN1045710C (fr)
AT (1)	ATE127792T1 (fr)
AU (1)	AU640645B2 (fr)
BG (1)	BG60561B1 (fr)
BR (1)	BR9002175A (fr)
CA (1)	CA2015366C (fr)
CZ (1)	CZ284824B6 (fr)
DD (1)	DD294166A5 (fr)
DE (1)	DE69022279T2 (fr)
DK (1)	DK0396427T3 (fr)
EG (1)	EG19504A (fr)
ES (1)	ES2077027T3 (fr)
FI (1)	FI102374B (fr)
GR (1)	GR3018083T3 (fr)
HU (1)	HU215229B (fr)
IL (1)	IL94265A (fr)
MA (1)	MA21832A1 (fr)
MX (1)	MX20597A (fr)
NO (1)	NO179368C (fr)
NZ (1)	NZ233552A (fr)
OA (1)	OA09207A (fr)
PL (1)	PL163579B1 (fr)
PT (1)	PT93967B (fr)
RO (1)	RO107253B1 (fr)
RU (1)	RU2077201C1 (fr)
SK (1)	SK207490A3 (fr)
TR (1)	TR24576A (fr)
ZA (1)	ZA903360B (fr)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5223525A (en) *	1989-05-05	1993-06-29	Rhone-Poulenc Ag Company	Pesticidal 1-arylimidazoles
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1990
- 1990-04-25 CA CA002015366A patent/CA2015366C/fr not_active Expired - Fee Related
- 1990-04-25 SK SK2074-90A patent/SK207490A3/sk unknown
- 1990-04-25 CZ CS902074A patent/CZ284824B6/cs not_active IP Right Cessation
- 1990-04-30 NO NO901926A patent/NO179368C/no not_active IP Right Cessation
- 1990-05-02 JP JP2116677A patent/JP2943993B2/ja not_active Expired - Fee Related
- 1990-05-02 AU AU54589/90A patent/AU640645B2/en not_active Ceased
- 1990-05-02 IL IL9426590A patent/IL94265A/en not_active IP Right Cessation
- 1990-05-03 NZ NZ233552A patent/NZ233552A/en unknown
- 1990-05-03 ZA ZA903360A patent/ZA903360B/xx unknown
- 1990-05-03 MA MA22097A patent/MA21832A1/fr unknown
- 1990-05-04 DE DE69022279T patent/DE69022279T2/de not_active Expired - Fee Related
- 1990-05-04 PL PL90285067A patent/PL163579B1/pl unknown
- 1990-05-04 MX MX2059790A patent/MX20597A/es unknown
- 1990-05-04 RU SU4743986/04A patent/RU2077201C1/ru not_active IP Right Cessation
- 1990-05-04 ES ES90304875T patent/ES2077027T3/es not_active Expired - Lifetime
- 1990-05-04 PT PT93967A patent/PT93967B/pt active IP Right Grant
- 1990-05-04 KR KR1019900006356A patent/KR0160512B1/ko not_active Expired - Fee Related
- 1990-05-04 FI FI902253A patent/FI102374B/fi not_active IP Right Cessation
- 1990-05-04 DK DK90304875.9T patent/DK0396427T3/da active
- 1990-05-04 DD DD90340400A patent/DD294166A5/de not_active IP Right Cessation
- 1990-05-04 HU HU902672A patent/HU215229B/hu not_active IP Right Cessation
- 1990-05-04 OA OA59785A patent/OA09207A/xx unknown
- 1990-05-04 AT AT90304875T patent/ATE127792T1/de not_active IP Right Cessation
- 1990-05-04 BG BG91928A patent/BG60561B1/bg unknown
- 1990-05-04 EP EP90304875A patent/EP0396427B1/fr not_active Expired - Lifetime
- 1990-05-05 RO RO144982A patent/RO107253B1/ro unknown
- 1990-05-05 CN CN90102488A patent/CN1045710C/zh not_active Expired - Fee Related
- 1990-05-06 EG EG26990A patent/EG19504A/xx active
- 1990-05-07 BR BR909002175A patent/BR9002175A/pt not_active IP Right Cessation
- 1990-05-17 TR TR90/0421A patent/TR24576A/xx unknown
1995
- 1995-11-15 GR GR950403201T patent/GR3018083T3/el unknown

Also Published As

Publication number	Publication date
EP0396427A1 (fr)	1990-11-07
CA2015366A1 (fr)	1990-11-05
IL94265A (en)	1995-03-30
BG91928A (bg)	1993-12-24
RO107253B1 (ro)	1993-10-30
BR9002175A (pt)	1991-08-13
ATE127792T1 (de)	1995-09-15
JP2943993B2 (ja)	1999-08-30
NO179368C (no)	1996-09-25
CZ284824B6 (cs)	1999-03-17
GR3018083T3 (en)	1996-02-29
EP0396427B1 (fr)	1995-09-13
CN1045710C (zh)	1999-10-20
TR24576A (tr)	1992-01-01
NO901926L (no)	1990-12-10
AU640645B2 (en)	1993-09-02
CZ207490A3 (cs)	1998-10-14
ES2077027T3 (es)	1995-11-16
PT93967A (pt)	1991-01-08
HU902672D0 (en)	1990-09-28
MA21832A1 (fr)	1990-12-31
FI102374B1 (fi)	1998-11-30
HU215229B (hu)	1999-01-28
EG19504A (en)	1995-06-29
MX20597A (es)	1994-02-28
DK0396427T3 (da)	1995-11-06
IL94265A0 (en)	1991-03-10
PT93967B (pt)	1996-07-31
NZ233552A (en)	1992-10-28
BG60561B1 (bg)	1995-08-28
AU5458990A (en)	1990-11-08
CA2015366C (fr)	2001-09-11
DD294166A5 (de)	1991-09-26
CN1046898A (zh)	1990-11-14
KR900018041A (ko)	1990-12-20
PL163579B1 (pl)	1994-04-29
DE69022279T2 (de)	1996-03-28
FI902253A0 (fi)	1990-05-04
OA09207A (en)	1992-06-30
SK279264B6 (sk)	1998-08-05
JPH0327361A (ja)	1991-02-05
PL285067A1 (en)	1991-01-14
RU2077201C1 (ru)	1997-04-20
DE69022279D1 (de)	1995-10-19
HUT54350A (en)	1991-02-28
FI102374B (fi)	1998-11-30
KR0160512B1 (ko)	1998-12-01
ZA903360B (en)	1992-01-29
NO179368B (no)	1996-06-17
NO901926D0 (no)	1990-04-30

Publication	Publication Date	Title
EP0460940B1 (fr)	1999-01-27	Aryl-1 pyrroles pesticides
KR100193403B1 (ko)	1999-06-15	살충성 1-아릴이미다졸
CZ281976B6 (cs)	1997-04-16	1-(2-pyridyl)pyrazoly, způsob jejich výroby a pesticidní prostředek tyto pyrazoly obsahující
CZ285842B6 (cs)	1999-11-17	3-Kyan-1-arylpyrazoly, prostředky, které je obsahují, způsob potírání členovců, nematodů, helminthů a prvoků za jejich použití a meziprodukty k jejich přípravě
EP0372982B1 (fr)	1997-07-02	Insecticides contenant des pyrroles
DE69022279T2 (de)	1996-03-28	1-Arylimidazol-Pestizide.
SK279252B6 (sk)	1998-08-05	1-aryl-5-(substituovaný alkylidénimino)pyrazoly, s
SK689989A3 (en)	1998-04-08	Pyrrole derivatives, insecticidal and acaricidal agent containing same and their use