IL99735A - 1-Arylimidazoles Pesticides - Google Patents
1-Arylimidazoles PesticidesInfo
- 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
Links
- 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
- 239000003960 organic solvent Substances 0.000 description 13
- 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
- 239000000725 suspension Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 239000003995 emulsifying agent Substances 0.000 description 11
- 239000004615 ingredient Substances 0.000 description 11
- 238000005507 spraying Methods 0.000 description 11
- 230000009466 transformation Effects 0.000 description 11
- 241000254173 Coleoptera Species 0.000 description 10
- 240000003768 Solanum lycopersicum Species 0.000 description 10
- 150000001335 aliphatic alkanes Chemical class 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 239000002917 insecticide Substances 0.000 description 10
- 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
- 239000000126 substance Substances 0.000 description 10
- 230000009885 systemic effect Effects 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 206010061217 Infestation Diseases 0.000 description 8
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 240000008042 Zea mays Species 0.000 description 8
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 8
- 230000029936 alkylation Effects 0.000 description 8
- 238000005804 alkylation reaction Methods 0.000 description 8
- 150000002513 isocyanates Chemical class 0.000 description 8
- 230000004048 modification Effects 0.000 description 8
- 238000012986 modification Methods 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 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
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 7
- 241000243786 Meloidogyne incognita Species 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 235000013601 eggs Nutrition 0.000 description 7
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- 241000462639 Epilachna varivestis Species 0.000 description 6
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 241001454293 Tetranychus urticae Species 0.000 description 6
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- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 235000005822 corn Nutrition 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
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- 238000011156 evaluation Methods 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 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
- 238000006722 reduction reaction Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 5
- QRZMXADUXZADTF-UHFFFAOYSA-N 4-aminoimidazole Chemical compound NC1=CNC=N1 QRZMXADUXZADTF-UHFFFAOYSA-N 0.000 description 5
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- 241000219146 Gossypium Species 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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- 150000001266 acyl halides Chemical class 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
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- 238000006481 deamination reaction Methods 0.000 description 5
- 125000004663 dialkyl amino group Chemical group 0.000 description 5
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 230000002140 halogenating effect Effects 0.000 description 5
- 238000005658 halogenation reaction Methods 0.000 description 5
- 150000004678 hydrides Chemical class 0.000 description 5
- 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
- 238000005991 sulfenylation reaction Methods 0.000 description 5
- 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
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 4
- 241000489976 Diabrotica undecimpunctata howardi Species 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- 241000258937 Hemiptera Species 0.000 description 4
- 241000257303 Hymenoptera Species 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 241000257159 Musca domestica Species 0.000 description 4
- 241000257226 Muscidae Species 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 241000238814 Orthoptera Species 0.000 description 4
- 241000488583 Panonychus ulmi Species 0.000 description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- 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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- POXSDSRWVJZWCN-UHFFFAOYSA-N triphenylphosphanium;iodide Chemical compound I.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 POXSDSRWVJZWCN-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 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
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 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
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes 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
-
- 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
-
- 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
- C07D233/86—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
- C07D233/88—Nitrogen atoms, e.g. allantoin
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (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)
- Inorganic Insulating Materials (AREA)
- Resistance Heating (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/606,518 US5223525A (en) | 1989-05-05 | 1990-10-31 | Pesticidal 1-arylimidazoles |
Publications (2)
Publication Number | Publication Date |
---|---|
IL99735A0 IL99735A0 (en) | 1992-08-18 |
IL99735A true IL99735A (en) | 1996-06-18 |
Family
ID=24428298
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL9973591A IL99735A (en) | 1990-10-31 | 1991-10-14 | 1-Arylimidazoles Pesticides |
Country Status (35)
Country | Link |
---|---|
US (1) | US5223525A (fr) |
EP (1) | EP0484165B1 (fr) |
JP (1) | JP3051535B2 (fr) |
KR (1) | KR100193403B1 (fr) |
CN (1) | CN1061965A (fr) |
AT (1) | ATE204258T1 (fr) |
AU (1) | AU655204B2 (fr) |
BG (1) | BG60966B1 (fr) |
BR (1) | BR9104749A (fr) |
CA (1) | CA2053716C (fr) |
CZ (1) | CZ284626B6 (fr) |
DE (1) | DE69132687T2 (fr) |
DK (1) | DK0484165T3 (fr) |
EC (1) | ECSP910787A (fr) |
EG (1) | EG19700A (fr) |
ES (1) | ES2162787T3 (fr) |
FI (1) | FI108032B (fr) |
HU (1) | HU214937B (fr) |
IE (1) | IE913801A1 (fr) |
IL (1) | IL99735A (fr) |
MA (1) | MA22334A1 (fr) |
MX (1) | MX9101892A (fr) |
MY (1) | MY106309A (fr) |
NO (1) | NO179516C (fr) |
NZ (1) | NZ240412A (fr) |
OA (1) | OA09901A (fr) |
PL (1) | PL168473B1 (fr) |
PT (1) | PT99386B (fr) |
RO (1) | RO110488B1 (fr) |
RU (1) | RU2072992C1 (fr) |
SK (1) | SK280538B6 (fr) |
TR (1) | TR25470A (fr) |
YU (1) | YU173591A (fr) |
ZA (1) | ZA918674B (fr) |
ZW (1) | ZW14791A1 (fr) |
Families Citing this family (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2716453B1 (fr) * | 1994-02-22 | 1996-03-29 | Rhone Poulenc Agrochimie | Procédé de sulfinylation de composés hétérocycliques. |
MY106533A (en) * | 1990-02-20 | 1995-06-30 | Sumitomo Chemical Co | A 4-tert.-butyl imidazole derivative and its production and use. |
EP0599183A1 (fr) * | 1992-11-25 | 1994-06-01 | Rhone-Poulenc Agrochimie | Fabrication des pesticides et leurs intermédiaires |
RU2126004C1 (ru) * | 1993-06-14 | 1999-02-10 | Пфайзер, Инк. | Производные имидазола или их фармацевтически приемлемые соли |
FR2712144B1 (fr) * | 1993-11-04 | 1997-07-18 | Rhone Poulenc Agrochimie | Association d'un fongicide à groupe azole avec un insecticide à groupe pyrazole, pyrrole ou phénylimidazole. |
FR2729825A1 (fr) * | 1995-01-30 | 1996-08-02 | Rhone Poulenc Agrochimie | Associations insecticides comprenant un insecticide de la famille des chloronicotinyls et un insecticide a groupe pyrazole,pyrrole ou phenylimidazole pour traiter les semences ou le sol |
US6136983A (en) * | 1995-06-05 | 2000-10-24 | Rhone-Poulenc Agrochimie | Pesticidal sulfur compounds |
US6060495A (en) * | 1995-06-05 | 2000-05-09 | Rhone-Poulenc Agrochimie | Pesticidal sulfur compounds |
US6060502A (en) * | 1995-06-05 | 2000-05-09 | Rhone-Poulenc Agrochimie | Pesticidal sulfur compounds |
FR2737085B1 (fr) * | 1995-07-26 | 1997-08-22 | Rhone Poulenc Agrochimie | Associations insecticides d'un oxime carbamate avec un insecticide a groupe pyrazole ou phenylimidazole |
US5939356A (en) * | 1996-06-21 | 1999-08-17 | Southwest Research Institute | Controlled release coated agricultural products |
DE69715769T2 (de) * | 1996-11-04 | 2003-05-28 | Bayer Cropscience S.A., Lyon | 1-Polyarylpyrazole als Pestizide |
JP3378017B2 (ja) * | 1996-12-26 | 2003-02-17 | 塩野義製薬株式会社 | イミダゾール誘導体の製造法 |
ZA981776B (en) | 1997-03-10 | 1998-09-03 | Rhone Poulenc Agrochimie | Pesticidal 1-arylpyrazoles |
CO5060426A1 (es) * | 1997-03-10 | 2001-07-30 | Rhone Poulenc Agrochimie | 1-aril-3-imidiopirazoles plaguicidas |
GB9810354D0 (en) * | 1998-05-14 | 1998-07-15 | Pfizer Ltd | Heterocycles |
FR2805971B1 (fr) | 2000-03-08 | 2004-01-30 | Aventis Cropscience Sa | Procedes de traitement et/ou de protection des cultures contre les arthropodes et compositions utiles pour de tels procedes |
JP2002097133A (ja) * | 2000-07-17 | 2002-04-02 | Shionogi & Co Ltd | トリアゼン化合物を含有する抗マラリア剤および殺線虫剤 |
US8440709B2 (en) | 2005-12-14 | 2013-05-14 | Makhteshim Chemical Works Ltd. | Polymorphs and amorphous forms of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile |
MX2009004323A (es) | 2006-11-10 | 2009-05-05 | Basf Se | Nueva modificacion cristalina. |
ES2368521T5 (es) | 2006-11-10 | 2015-02-18 | Basf Se | Modificación cristalina de fipronil |
UA110598C2 (uk) | 2006-11-10 | 2016-01-25 | Басф Се | Спосіб одержання кристалічної модифікації фіпронілу |
BRPI0718720A2 (pt) | 2006-11-10 | 2013-12-03 | Basf Se | Fipronil sólido, processo para preparar a modificação cristalina v, mistura pesticida ou parasiticida sinergística, composição pesticida ou parasiticida, uso do fipronil sólido ou da mistura ou da composição, métodos para controlar pragas, para proteger uma planta da infestação e ataque por pragas e para protefer semente e para tratar, controlar, previnir ou proteger animais contra infestação ou infecção por parasitas, semente, e, processo para preparar uma composição para tratar, controlar, prevenir ou proteger animais contra infestação ou infecção por parasitas. |
GB0806745D0 (en) * | 2008-04-14 | 2008-05-14 | Syngenta Participations Ag | Novel imidazole derivatives |
US8431699B2 (en) * | 2009-02-27 | 2013-04-30 | Vertichem Corporation | Method for manufacture of 2-oxoimidazolidines |
GB0904315D0 (en) * | 2009-03-12 | 2009-04-22 | Syngenta Participations Ag | Novel imidazole derivatives |
AU2012100035A4 (en) | 2011-01-14 | 2012-02-09 | Keki Hormusji Gharda | Polymorphism in 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoro methyl sulfinyl pyrazole |
US10058542B1 (en) | 2014-09-12 | 2018-08-28 | Thioredoxin Systems Ab | Composition comprising selenazol or thiazolone derivatives and silver and method of treatment therewith |
WO2017189348A1 (fr) | 2016-04-25 | 2017-11-02 | Bayer Cropscience Lp | Formulation et procédé pour lutter contre des acariens varroa |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ212209A (en) * | 1984-05-29 | 1988-08-30 | Pfizer | Quinolone derivatives and pharmaceutical compositions |
DE3608143A1 (de) * | 1986-03-12 | 1987-09-17 | Hoechst Ag | 1-phenylimidazolcarbonsaeureamide, ihre herstellung sowie ihre verwendung als wachstumsregulatoren |
DK570987A (da) * | 1986-12-01 | 1988-06-02 | Hoffmann La Roche | Oxadiazol-, thiadiazol- og triazolforbindelser |
IL85556A (en) * | 1987-03-05 | 1994-06-24 | May & Baker Ltd | Method for exterminating pests using a history of 2-phenylimidazole, certain compounds of this type and a process for their preparation |
CA1339133C (fr) * | 1987-03-13 | 1997-07-29 | Rikuo Nasu | Derives de l'imidazole et compositions a base de ces derives pour l'elimination d'organismes nuisibles |
IL86134A (en) * | 1987-05-02 | 1993-06-10 | Basf Ag | N-substituted azoles, their manufacture and their use as pesticides and compositions containing them |
CZ284824B6 (cs) * | 1989-05-05 | 1999-03-17 | Rhone-Poulenc Agrochimie | 1-Arylimidazoly, způsob jejich výroby a meziprodukty v tomto způsobu, prostředky, které je obsahují a jejich použití |
-
1990
- 1990-10-31 US US07/606,518 patent/US5223525A/en not_active Expired - Fee Related
-
1991
- 1991-10-14 IL IL9973591A patent/IL99735A/en not_active IP Right Cessation
- 1991-10-15 AU AU85847/91A patent/AU655204B2/en not_active Ceased
- 1991-10-18 CA CA002053716A patent/CA2053716C/fr not_active Expired - Fee Related
- 1991-10-21 RO RO148609A patent/RO110488B1/ro unknown
- 1991-10-23 EC EC1991000787A patent/ECSP910787A/es unknown
- 1991-10-28 EG EG65691A patent/EG19700A/xx active
- 1991-10-29 CZ CS913278A patent/CZ284626B6/cs not_active IP Right Cessation
- 1991-10-29 ZW ZW147/91A patent/ZW14791A1/xx unknown
- 1991-10-29 PL PL91292211A patent/PL168473B1/pl not_active IP Right Cessation
- 1991-10-29 NO NO914230A patent/NO179516C/no not_active IP Right Cessation
- 1991-10-29 SK SK3278-91A patent/SK280538B6/sk unknown
- 1991-10-30 IE IE380191A patent/IE913801A1/en not_active Application Discontinuation
- 1991-10-30 MY MYPI91002011A patent/MY106309A/en unknown
- 1991-10-30 NZ NZ240412A patent/NZ240412A/en unknown
- 1991-10-30 FI FI915116A patent/FI108032B/fi not_active IP Right Cessation
- 1991-10-30 PT PT99386A patent/PT99386B/pt not_active IP Right Cessation
- 1991-10-30 MA MA22616A patent/MA22334A1/fr unknown
- 1991-10-30 RU SU915010300A patent/RU2072992C1/ru not_active IP Right Cessation
- 1991-10-30 BG BG95400A patent/BG60966B1/bg unknown
- 1991-10-30 HU HU414/91A patent/HU214937B/hu not_active IP Right Cessation
- 1991-10-31 ZA ZA918674A patent/ZA918674B/xx unknown
- 1991-10-31 DK DK91310094T patent/DK0484165T3/da active
- 1991-10-31 YU YU173591A patent/YU173591A/sh unknown
- 1991-10-31 AT AT91310094T patent/ATE204258T1/de not_active IP Right Cessation
- 1991-10-31 JP JP3349314A patent/JP3051535B2/ja not_active Expired - Fee Related
- 1991-10-31 BR BR919104749A patent/BR9104749A/pt not_active IP Right Cessation
- 1991-10-31 TR TR91/1059A patent/TR25470A/xx unknown
- 1991-10-31 OA OA60091A patent/OA09901A/fr unknown
- 1991-10-31 MX MX9101892A patent/MX9101892A/es not_active IP Right Cessation
- 1991-10-31 EP EP91310094A patent/EP0484165B1/fr not_active Expired - Lifetime
- 1991-10-31 DE DE69132687T patent/DE69132687T2/de not_active Expired - Fee Related
- 1991-10-31 KR KR1019910019310A patent/KR100193403B1/ko not_active IP Right Cessation
- 1991-10-31 CN CN91110473A patent/CN1061965A/zh active Pending
- 1991-10-31 ES ES91310094T patent/ES2162787T3/es not_active Expired - Lifetime
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Legal Events
Date | Code | Title | Description |
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FF | Patent granted | ||
KB | Patent renewed | ||
KB | Patent renewed | ||
KB | Patent renewed | ||
MM9K | Patent not in force due to non-payment of renewal fees |