IL99735A - 1-Arylimidazoles Pesticides - Google Patents

Info

Publication number

IL99735A

IL99735A IL9973591A IL9973591A IL99735A IL 99735 A IL99735 A IL 99735A IL 9973591 A IL9973591 A IL 9973591A IL 9973591 A IL9973591 A IL 9973591A IL 99735 A IL99735 A IL 99735A

Authority

IL

Israel

Prior art keywords

formula

compound

bromo

dichloro

alkyl

Prior art date

1990-10-31

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims abstract description 268
• 239000000203 mixture Substances 0.000 title claims abstract description 136
• 241000238421 Arthropoda Species 0.000 title claims abstract description 45
• 230000008569 process Effects 0.000 title claims abstract description 40
• 241000244206 Nematoda Species 0.000 title claims abstract description 29
• 244000000013 helminth Species 0.000 title claims abstract description 23
• -1 1-(substituted)phenylimidazoles Chemical class 0.000 title claims description 92
• 238000002360 preparation method Methods 0.000 title claims description 40
• 150000001875 compounds Chemical class 0.000 claims abstract description 453
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 70
• 239000001257 hydrogen Substances 0.000 claims abstract description 67
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 53
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 48
• 150000002367 halogens Chemical group 0.000 claims abstract description 46
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 40
• 125000004647 alkyl sulfenyl group Chemical group 0.000 claims abstract description 33
• 241000238876 Acari Species 0.000 claims abstract description 29
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 25
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 23
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 22
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 22
• 241000238631 Hexapoda Species 0.000 claims abstract description 17
• 125000005843 halogen group Chemical group 0.000 claims abstract description 13
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 11
• 241001124076 Aphididae Species 0.000 claims abstract description 9
• 238000006243 chemical reaction Methods 0.000 claims description 103
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 85
• 241000196324 Embryophyta Species 0.000 claims description 57
• 241000607479 Yersinia pestis Species 0.000 claims description 46
• 239000004480 active ingredient Substances 0.000 claims description 38
• 150000002431 hydrogen Chemical class 0.000 claims description 35
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 35
• 239000002689 soil Substances 0.000 claims description 28
• 238000011282 treatment Methods 0.000 claims description 27
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 25
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
• 239000002253 acid Substances 0.000 claims description 23
• 239000003795 chemical substances by application Substances 0.000 claims description 23
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 22
• 239000007787 solid Substances 0.000 claims description 21
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 20
• 239000007788 liquid Substances 0.000 claims description 19
• 239000003153 chemical reaction reagent Substances 0.000 claims description 15
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 15
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 15
• 229910052751 metal Inorganic materials 0.000 claims description 15
• 239000002184 metal Substances 0.000 claims description 15
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 14
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 14
• 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 13
• 229910052794 bromium Inorganic materials 0.000 claims description 13
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
• 108010034145 Helminth Proteins Proteins 0.000 claims description 11
• 239000003638 chemical reducing agent Substances 0.000 claims description 11
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
• 125000004432 carbon atom Chemical group C* 0.000 claims description 10
• 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 10
• 239000002168 alkylating agent Substances 0.000 claims description 9
• 229940100198 alkylating agent Drugs 0.000 claims description 9
• 244000144972 livestock Species 0.000 claims description 9
• 238000006467 substitution reaction Methods 0.000 claims description 9
• 239000002841 Lewis acid Substances 0.000 claims description 8
• 150000007517 lewis acids Chemical class 0.000 claims description 8
• 239000004094 surface-active agent Substances 0.000 claims description 8
• 239000007983 Tris buffer Substances 0.000 claims description 7
• 241000251539 Vertebrata <Metazoa> Species 0.000 claims description 7
• 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 claims description 7
• 239000007800 oxidant agent Substances 0.000 claims description 7
• 239000012279 sodium borohydride Substances 0.000 claims description 7
• 229910000033 sodium borohydride Inorganic materials 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 6
• 230000007062 hydrolysis Effects 0.000 claims description 6
• 238000006460 hydrolysis reaction Methods 0.000 claims description 6
• 239000012430 organic reaction media Substances 0.000 claims description 6
• 230000005180 public health Effects 0.000 claims description 6
• 238000010791 quenching Methods 0.000 claims description 6
• 230000000171 quenching effect Effects 0.000 claims description 6
• 150000003457 sulfones Chemical class 0.000 claims description 6
• 150000003462 sulfoxides Chemical class 0.000 claims description 6
• 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 6
• BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 5
• 239000012954 diazonium Substances 0.000 claims description 5
• 150000001989 diazonium salts Chemical class 0.000 claims description 5
• 239000000969 carrier Substances 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• 229910052740 iodine Inorganic materials 0.000 claims description 4
• 230000002829 reductive effect Effects 0.000 claims description 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
• ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 claims description 3
• BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 3
• ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 3
• 230000002152 alkylating effect Effects 0.000 claims description 3
• 239000012039 electrophile Substances 0.000 claims description 3
• YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 claims description 3
• ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 3
• 238000012423 maintenance Methods 0.000 claims description 3
• 125000001979 organolithium group Chemical group 0.000 claims description 3
• 230000003071 parasitic effect Effects 0.000 claims description 3
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 3
• 150000003512 tertiary amines Chemical class 0.000 claims description 3
• 239000002671 adjuvant Substances 0.000 claims description 2
• 150000002978 peroxides Chemical class 0.000 claims description 2
• WDMDYWZDHMAQDN-UHFFFAOYSA-N 5-bromo-1-(2,6-dichloro-4-fluorophenyl)-4-(trifluoromethylsulfonyl)imidazole Chemical compound ClC1=CC(F)=CC(Cl)=C1N1C(Br)=C(S(=O)(=O)C(F)(F)F)N=C1 WDMDYWZDHMAQDN-UHFFFAOYSA-N 0.000 claims 2
• SVOCLWUDDWXHFW-UHFFFAOYSA-N 2-methylsulfanyl-1h-imidazole Chemical compound CSC1=NC=CN1 SVOCLWUDDWXHFW-UHFFFAOYSA-N 0.000 claims 1
• NDNDWAYUAQDAEN-UHFFFAOYSA-N 4-chloro-2-(difluoromethylsulfanyl)-5-methylsulfanyl-1-(2,4,6-trichlorophenyl)imidazole Chemical compound CSC1=C(Cl)N=C(SC(F)F)N1C1=C(Cl)C=C(Cl)C=C1Cl NDNDWAYUAQDAEN-UHFFFAOYSA-N 0.000 claims 1
• UVMIAHSJKIRUSA-UHFFFAOYSA-N 5-bromo-4-chloro-1-(2,6-dibromo-4-fluorophenyl)-2-(difluoromethylsulfanyl)imidazole Chemical compound FC(F)SC1=NC(Cl)=C(Br)N1C1=C(Br)C=C(F)C=C1Br UVMIAHSJKIRUSA-UHFFFAOYSA-N 0.000 claims 1
• WFKWFAPZPDMCFS-UHFFFAOYSA-N 5-bromo-4-chloro-1-(2,6-dichloro-4-fluorophenyl)-2-(difluoromethylsulfanyl)imidazole Chemical compound FC(F)SC1=NC(Cl)=C(Br)N1C1=C(Cl)C=C(F)C=C1Cl WFKWFAPZPDMCFS-UHFFFAOYSA-N 0.000 claims 1
• QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 1
• 229910052731 fluorine Inorganic materials 0.000 claims 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
• 239000000543 intermediate Substances 0.000 abstract description 132
• 125000001424 substituent group Chemical group 0.000 abstract description 22
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 102
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
• 239000002904 solvent Substances 0.000 description 55
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 49
• 238000012360 testing method Methods 0.000 description 45
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
• 239000000243 solution Substances 0.000 description 41
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
• 241001465754 Metazoa Species 0.000 description 27
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 27
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
• 239000000047 product Substances 0.000 description 23
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
• 150000003839 salts Chemical class 0.000 description 22
• 238000009472 formulation Methods 0.000 description 21
• 239000003921 oil Substances 0.000 description 21
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
• 239000002585 base Substances 0.000 description 20
• 230000015572 biosynthetic process Effects 0.000 description 20
• 235000019198 oils Nutrition 0.000 description 20
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• 239000000843 powder Substances 0.000 description 17
• 238000003786 synthesis reaction Methods 0.000 description 17
• 239000008187 granular material Substances 0.000 description 16
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
• 239000007921 spray Substances 0.000 description 15
• WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 13
• 229960001701 chloroform Drugs 0.000 description 13
• 239000012442 inert solvent Substances 0.000 description 13
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• 241000255925 Diptera Species 0.000 description 12
• 241001521235 Spodoptera eridania Species 0.000 description 12
• 150000001412 amines Chemical class 0.000 description 12
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 12
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• 241000254173 Coleoptera Species 0.000 description 10
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• 150000001335 aliphatic alkanes Chemical class 0.000 description 10
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• 230000000361 pesticidal effect Effects 0.000 description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
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• 235000007688 Lycopersicon esculentum Nutrition 0.000 description 8
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• 235000002017 Zea mays subsp mays Nutrition 0.000 description 8
• 230000029936 alkylation Effects 0.000 description 8
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• QFMDFTQOJHFVNR-UHFFFAOYSA-N 1-[2,2-dichloro-1-(4-ethylphenyl)ethyl]-4-ethylbenzene Chemical compound C1=CC(CC)=CC=C1C(C(Cl)Cl)C1=CC=C(CC)C=C1 QFMDFTQOJHFVNR-UHFFFAOYSA-N 0.000 description 7
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• 125000003277 amino group Chemical group 0.000 description 7
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• 150000002148 esters Chemical class 0.000 description 7
• 125000002883 imidazolyl group Chemical group 0.000 description 7
• 239000012948 isocyanate Substances 0.000 description 7
• 238000007254 oxidation reaction Methods 0.000 description 7
• 241000894007 species Species 0.000 description 7
• 241001600408 Aphis gossypii Species 0.000 description 6
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• 241000462639 Epilachna varivestis Species 0.000 description 6
• 201000007224 Myeloproliferative neoplasm Diseases 0.000 description 6
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• 125000000304 alkynyl group Chemical group 0.000 description 6
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• 201000010099 disease Diseases 0.000 description 6
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• UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 6
• 230000009467 reduction Effects 0.000 description 6
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• QRZMXADUXZADTF-UHFFFAOYSA-N 4-aminoimidazole Chemical compound NC1=CNC=N1 QRZMXADUXZADTF-UHFFFAOYSA-N 0.000 description 5
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• 125000003118 aryl group Chemical group 0.000 description 5
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• 125000004663 dialkyl amino group Chemical group 0.000 description 5
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• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
• 239000003381 stabilizer Substances 0.000 description 5
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• IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 5
• 238000010998 test method Methods 0.000 description 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
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• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
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