JPH06511260A - イミダゾール誘導体 - Google Patents

イミダゾール誘導体

Info

Publication number: JPH06511260A
Authority: JP; Japan
Prior art keywords: formula; hydrogen; alkyl; halogen; haloalkyl
Prior art date: 1992-07-13
Legal status (The legal status 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 status listed.): Pending

Application number

JP6502902A

Other languages

English (en)

Japanese (ja)

Inventor

ヒルデンブラント，クリストフ

ゲールト，ジャン−クロード

ティネンバール，オリビエール

Original Assignee

チバ−ガイギー　アクチェンゲゼルシャフト

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.)

1992-07-13

Filing date

1993-06-30

Publication date

1994-12-15

1993-06-30 Application filed by チバ−ガイギー　アクチェンゲゼルシャフト filed Critical チバ−ガイギー　アクチェンゲゼルシャフト

1994-12-15 Publication of JPH06511260A publication Critical patent/JPH06511260A/ja

Status Pending legal-status Critical Current

Links

150000002460 imidazoles Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 157
229910052739 hydrogen Inorganic materials 0.000 claims description 92
239000001257 hydrogen Substances 0.000 claims description 92
150000002431 hydrogen Chemical group 0.000 claims description 81
125000000217 alkyl group Chemical group 0.000 claims description 66
229910052736 halogen Inorganic materials 0.000 claims description 64
150000002367 halogens Chemical group 0.000 claims description 64
239000000203 mixture Substances 0.000 claims description 59
125000001188 haloalkyl group Chemical group 0.000 claims description 57
241001465754 Metazoa Species 0.000 claims description 40
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 39
-1 C1-C6 haloar Rukoxy Chemical group 0.000 claims description 37
239000004480 active ingredient Substances 0.000 claims description 34
125000003545 alkoxy group Chemical group 0.000 claims description 29
238000000034 method Methods 0.000 claims description 27
239000000126 substance Substances 0.000 claims description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
241000238631 Hexapoda Species 0.000 claims description 20
239000000460 chlorine Chemical group 0.000 claims description 20
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
125000004093 cyano group Chemical group *C#N 0.000 claims description 19
229910052760 oxygen Inorganic materials 0.000 claims description 19
239000001301 oxygen Substances 0.000 claims description 19
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
239000011593 sulfur Chemical group 0.000 claims description 17
229910052717 sulfur Inorganic materials 0.000 claims description 17
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 16
125000002947 alkylene group Chemical group 0.000 claims description 14
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 13
229910052801 chlorine Inorganic materials 0.000 claims description 13
125000004995 haloalkylthio group Chemical group 0.000 claims description 13
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
229910052731 fluorine Inorganic materials 0.000 claims description 12
241000607479 Yersinia pestis Species 0.000 claims description 11
125000004966 cyanoalkyl group Chemical group 0.000 claims description 11
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
239000011737 fluorine Chemical group 0.000 claims description 10
238000009472 formulation Methods 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
230000000507 anthelmentic effect Effects 0.000 claims description 9
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 9
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical group ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims description 7
229910052740 iodine Inorganic materials 0.000 claims description 7
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
230000029936 alkylation Effects 0.000 claims description 6
238000005804 alkylation reaction Methods 0.000 claims description 6
125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
244000000013 helminth Species 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
239000007800 oxidant agent Substances 0.000 claims description 4
241000238876 Acari Species 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 2
239000000575 pesticide Substances 0.000 claims description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 15
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 10
125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 7
125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims 7
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
XGDRLCRGKUCBQL-UHFFFAOYSA-N 1h-imidazole-4,5-dicarbonitrile Chemical class N#CC=1N=CNC=1C#N XGDRLCRGKUCBQL-UHFFFAOYSA-N 0.000 claims 6
125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 5
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 5
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 3
241000238421 Arthropoda Species 0.000 claims 3
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 claims 3
125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 1
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims 1
125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
MRRBAEJGLOLWCX-UPHRSURJSA-N (z)-2,3-diaminobut-2-enedioic acid Chemical compound OC(=O)C(/N)=C(/N)C(O)=O MRRBAEJGLOLWCX-UPHRSURJSA-N 0.000 claims 1
241001533303 Acarinae Species 0.000 claims 1
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 1
125000002883 imidazolyl group Chemical group 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
125000003944 tolyl group Chemical group 0.000 claims 1
241000894007 species Species 0.000 description 33
241000196324 Embryophyta Species 0.000 description 18
230000000694 effects Effects 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
241000244206 Nematoda Species 0.000 description 15
239000004094 surface-active agent Substances 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
125000004438 haloalkoxy group Chemical group 0.000 description 14
239000000243 solution Substances 0.000 description 14
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
239000007787 solid Substances 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000012141 concentrate Substances 0.000 description 12
235000008504 concentrate Nutrition 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
241001494479 Pecora Species 0.000 description 11
244000045947 parasite Species 0.000 description 11
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 10
125000004414 alkyl thio group Chemical group 0.000 description 10
244000144972 livestock Species 0.000 description 10
150000003839 salts Chemical class 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000002202 Polyethylene glycol Substances 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
229920001223 polyethylene glycol Polymers 0.000 description 9
229910052783 alkali metal Inorganic materials 0.000 description 8
239000005995 Aluminium silicate Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
239000002671 adjuvant Substances 0.000 description 7
235000012211 aluminium silicate Nutrition 0.000 description 7
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
235000013399 edible fruits Nutrition 0.000 description 7
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
239000000843 powder Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 6
239000002585 base Substances 0.000 description 6
239000000839 emulsion Substances 0.000 description 6
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
229920000728 polyester Polymers 0.000 description 6
239000011734 sodium Substances 0.000 description 6
239000002689 soil Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
239000003826 tablet Substances 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
239000000654 additive Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000008187 granular material Substances 0.000 description 5
238000002347 injection Methods 0.000 description 5
239000007924 injection Substances 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000002736 nonionic surfactant Substances 0.000 description 5
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 5
235000012239 silicon dioxide Nutrition 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
241000283690 Bos taurus Species 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
241000869417 Trematodes Species 0.000 description 4
230000000895 acaricidal effect Effects 0.000 description 4
230000037396 body weight Effects 0.000 description 4
235000013339 cereals Nutrition 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
235000013601 eggs Nutrition 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
238000001914 filtration Methods 0.000 description 4
150000007529 inorganic bases Chemical class 0.000 description 4
239000002917 insecticide Substances 0.000 description 4
239000011630 iodine Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
235000016068 Berberis vulgaris Nutrition 0.000 description 3
241000335053 Beta vulgaris Species 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
241000283707 Capra Species 0.000 description 3
229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
241000282985 Cervus Species 0.000 description 3
229920002261 Corn starch Polymers 0.000 description 3
229920000742 Cotton Polymers 0.000 description 3
241000283086 Equidae Species 0.000 description 3
241000282326 Felis catus Species 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
240000007594 Oryza sativa Species 0.000 description 3
235000007164 Oryza sativa Nutrition 0.000 description 3
241000286209 Phasianidae Species 0.000 description 3
229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
239000002262 Schiff base Substances 0.000 description 3
150000004753 Schiff bases Chemical class 0.000 description 3
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239000003905 agrochemical Substances 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
239000011575 calcium Substances 0.000 description 3
239000002775 capsule Substances 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
150000004649 carbonic acid derivatives Chemical class 0.000 description 3
239000001768 carboxy methyl cellulose Substances 0.000 description 3
235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
239000008112 carboxymethyl-cellulose Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000004359 castor oil Substances 0.000 description 3
235000019438 castor oil Nutrition 0.000 description 3
239000003240 coconut oil Substances 0.000 description 3
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238000001816 cooling Methods 0.000 description 3
239000008120 corn starch Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
150000004665 fatty acids Chemical class 0.000 description 3
230000000855 fungicidal effect Effects 0.000 description 3
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
150000004679 hydroxides Chemical class 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000012528 membrane Substances 0.000 description 3
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239000001923 methylcellulose Substances 0.000 description 3
235000010981 methylcellulose Nutrition 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 3
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102000004169 proteins and genes Human genes 0.000 description 3
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239000008096 xylene Substances 0.000 description 3
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
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LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
229910021532 Calcite Inorganic materials 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
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240000008067 Cucumis sativus Species 0.000 description 2
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235000010469 Glycine max Nutrition 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
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239000005642 Oleic acid Substances 0.000 description 2
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235000010582 Pisum sativum Nutrition 0.000 description 2
240000004713 Pisum sativum Species 0.000 description 2
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241001136903 Rhagoletis pomonella Species 0.000 description 2
241001481703 Rhipicephalus <genus> Species 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
235000002595 Solanum tuberosum Nutrition 0.000 description 2
244000061456 Solanum tuberosum Species 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
241000189578 Taeniothrips Species 0.000 description 2
241000242541 Trematoda Species 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
240000006677 Vicia faba Species 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
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CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
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ROWMQJJMCWDJDT-UHFFFAOYSA-N tribromomethane Chemical compound Br[C](Br)Br ROWMQJJMCWDJDT-UHFFFAOYSA-N 0.000 description 1
ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Environmental Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Dentistry (AREA)
Plant Pathology (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Pest Control & Pesticides (AREA)
Tropical Medicine & Parasitology (AREA)
Agronomy & Crop Science (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

JP6502902A 1992-07-13 1993-06-30 イミダゾール誘導体 Pending JPH06511260A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH221992		1992-07-13
CH2219/92-5		1992-07-13
PCT/EP1993/001682 WO1994001432A1 (en)	1992-07-13	1993-06-30	Imidazole derivatives

Publications (1)

Publication Number	Publication Date
JPH06511260A true JPH06511260A (ja)	1994-12-15

Family

ID=4228643

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP6502902A Pending JPH06511260A (ja)	1992-07-13	1993-06-30	イミダゾール誘導体

Country Status (5)

Country	Link
EP (1)	EP0603377A1 (de)
JP (1)	JPH06511260A (de)
AU (1)	AU4561993A (de)
CA (1)	CA2116455A1 (de)
WO (1)	WO1994001432A1 (de)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL85556A (en) *	1987-03-05	1994-06-24	May & Baker Ltd	Pesticidal method using 2-phenylimidazole derivatives, some such novel compounds and process for their preparation
EP0420805A3 (en) *	1989-09-26	1991-10-16	Ciba-Geigy Ag	Anthelmintic compounds

1993
- 1993-06-30 CA CA002116455A patent/CA2116455A1/en not_active Abandoned
- 1993-06-30 EP EP93915749A patent/EP0603377A1/de not_active Withdrawn
- 1993-06-30 AU AU45619/93A patent/AU4561993A/en not_active Abandoned
- 1993-06-30 JP JP6502902A patent/JPH06511260A/ja active Pending
- 1993-06-30 WO PCT/EP1993/001682 patent/WO1994001432A1/en not_active Ceased

Also Published As

Publication number	Publication date
EP0603377A1 (de)	1994-06-29
WO1994001432A1 (en)	1994-01-20
AU4561993A (en)	1994-01-31
CA2116455A1 (en)	1994-01-20

Publication	Publication Date	Title
AU599313B2 (en)	1990-07-19	Acyl ureas for controlling endoparasites and ectoparasites
AU676343B2 (en)	1997-03-06	Pesticidal 1-arylpyrroles
KR100216159B1 (ko)	1999-08-16	피콜린 옥사이드 및 그의 제조방법
AU2022219182A1 (en)	2023-08-24	Substituted isoxazoline derivatives
JPS6197261A (ja)	1986-05-15	有害生物防除剤
JPS59176245A (ja)	1984-10-05	ベンゾイル尿素化合物、その製造方法並びに該ベンゾイル尿素化合物を有効成分とする殺虫殺ダニ剤組成物
WO1998039972A1 (en)	1998-09-17	Pesticidal combination
HUT56053A (en)	1991-07-29	Process for producing derivatives of butiric acid, and insecticide compositions containing them
US6057355A (en)	2000-05-02	Pesticidal combination
JPH06511260A (ja)	1994-12-15	イミダゾール誘導体
US5610038A (en)	1997-03-11	Thiangazole, its preparation, compositions and use thereof
WO2023104564A1 (en)	2023-06-15	Pyrazine compounds for the control of invertebrate pests
JPH07501084A (ja)	1995-02-02	４，５−ジシアノイミダゾール誘導体及びそれらを含む農薬（ｐｅｓｔｉｃｉｄａｌ）組成物
AU659423B2 (en)	1995-05-18	Thiangazole, its preparation, compositions and use thereof
AU2024290866A1 (en)	2026-01-08	Triazole compounds for the control of invertebrate pests
WO2025008250A1 (en)	2025-01-09	Triazole compounds for the control of invertebrate pests
HUT63608A (en)	1993-09-28	Insecticidal compositions comprising butyric acid amide derivatives as active ingredient and process for producing the active ingredients and for killing insects
DE4200742A1 (de)	1992-07-23	Iminomethylpyrazole
WO2003086077A1 (en)	2003-10-23	Compositions for animal tick or flea control
EP0661281A1 (de)	1995-07-05	Substituierte phenylether
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