JPS6055070B2 - イミダゾリル−プロピオニトリル、その製造法及び該化合物を含有する殺菌剤 - Google Patents
イミダゾリル−プロピオニトリル、その製造法及び該化合物を含有する殺菌剤Info
- Publication number
- JPS6055070B2 JPS6055070B2 JP57106257A JP10625782A JPS6055070B2 JP S6055070 B2 JPS6055070 B2 JP S6055070B2 JP 57106257 A JP57106257 A JP 57106257A JP 10625782 A JP10625782 A JP 10625782A JP S6055070 B2 JPS6055070 B2 JP S6055070B2
- Authority
- JP
- Japan
- Prior art keywords
- propionitrile
- imidazol
- compound according
- group
- hydrogen nitrate
- Prior art date
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title claims description 130
- 239000000417 fungicide Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- PAPPEKHULAQSEJ-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)propanenitrile Chemical compound N#CC(C)C1=NC=CN1 PAPPEKHULAQSEJ-UHFFFAOYSA-N 0.000 title claims 2
- -1 propalkyl group Chemical group 0.000 claims description 88
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 76
- 229910017604 nitric acid Inorganic materials 0.000 claims description 66
- 230000000855 fungicidal effect Effects 0.000 claims description 29
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 230000012010 growth Effects 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 230000000844 anti-bacterial effect Effects 0.000 claims description 4
- CUPDXNVZLUHLPG-UHFFFAOYSA-N 2-(2-chlorophenyl)-3-imidazol-1-yl-2-propoxypropanenitrile Chemical compound ClC1=C(C=CC=C1)C(C#N)(CN1C=NC=C1)OCCC CUPDXNVZLUHLPG-UHFFFAOYSA-N 0.000 claims description 3
- SUPDEAABRCKILZ-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-imidazol-1-yl-2-propoxypropanenitrile Chemical compound ClC1=CC=C(C=C1)C(C#N)(CN1C=NC=C1)OCCC SUPDEAABRCKILZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- HJNUVCLGGKUJGW-UHFFFAOYSA-N 2-propoxypropanenitrile Chemical compound CCCOC(C)C#N HJNUVCLGGKUJGW-UHFFFAOYSA-N 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 8
- GMMHWGXHKPJLPQ-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-hexoxy-3-imidazol-1-ylpropanenitrile Chemical compound ClC1=CC=C(C=C1)C(C#N)(CN1C=NC=C1)OCCCCCC GMMHWGXHKPJLPQ-UHFFFAOYSA-N 0.000 claims 4
- XEQIISVRKIKCLQ-UHFFFAOYSA-N 3-imidazol-1-ylpropanenitrile Chemical compound N#CCCN1C=CN=C1 XEQIISVRKIKCLQ-UHFFFAOYSA-N 0.000 claims 4
- NVAOLENBKNECGF-UHFFFAOYSA-N 2-phenylpropanenitrile Chemical compound N#CC(C)C1=CC=CC=C1 NVAOLENBKNECGF-UHFFFAOYSA-N 0.000 claims 3
- VNCJLZOQMJWQGQ-UHFFFAOYSA-N 2-(2-fluorophenyl)-3-imidazol-1-yl-2-propoxypropanenitrile Chemical compound FC1=C(C=CC=C1)C(C#N)(CN1C=NC=C1)OCCC VNCJLZOQMJWQGQ-UHFFFAOYSA-N 0.000 claims 2
- WOORJRTUBDSICD-UHFFFAOYSA-N 2-(3,3-dimethylbutan-2-yloxy)-3-imidazol-1-yl-2-phenylpropanenitrile Chemical compound N1(C=NC=C1)CC(C#N)(OC(C(C)(C)C)C)C1=CC=CC=C1 WOORJRTUBDSICD-UHFFFAOYSA-N 0.000 claims 2
- KMLMPALZGFTQQN-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-2-ethoxy-3-imidazol-1-ylpropanenitrile Chemical compound C(C)OC(C#N)(CN1C=NC=C1)C1=CC(=C(C=C1)Cl)Cl KMLMPALZGFTQQN-UHFFFAOYSA-N 0.000 claims 2
- JESFENYHIFEEKY-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-3-imidazol-1-yl-2-propoxypropanenitrile Chemical compound ClC=1C=C(C=CC1Cl)C(C#N)(CN1C=NC=C1)OCCC JESFENYHIFEEKY-UHFFFAOYSA-N 0.000 claims 2
- FCXNKACBCFFDIL-UHFFFAOYSA-N 2-(4-bromophenyl)-2-butoxy-3-imidazol-1-ylpropanenitrile Chemical compound BrC1=CC=C(C=C1)C(C#N)(CN1C=NC=C1)OCCCC FCXNKACBCFFDIL-UHFFFAOYSA-N 0.000 claims 2
- SWKUVNPTOICCGA-UHFFFAOYSA-N 2-(4-bromophenyl)-3-imidazol-1-yl-2-propoxypropanenitrile Chemical compound BrC1=CC=C(C=C1)C(C#N)(CN1C=NC=C1)OCCC SWKUVNPTOICCGA-UHFFFAOYSA-N 0.000 claims 2
- JGUQBUBHBYVBPO-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-imidazol-1-yl-2-methoxypropanenitrile Chemical compound FC1=CC=C(C=C1)C(C#N)(CN1C=NC=C1)OC JGUQBUBHBYVBPO-UHFFFAOYSA-N 0.000 claims 2
- GCMYUCTWVNAZEQ-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-imidazol-1-yl-2-propoxypropanenitrile Chemical compound FC1=CC=C(C=C1)C(C#N)(CN1C=NC=C1)OCCC GCMYUCTWVNAZEQ-UHFFFAOYSA-N 0.000 claims 2
- SXXFKLQXHTWSLT-UHFFFAOYSA-N 2-butoxy-2-(2,4-dichlorophenyl)-3-imidazol-1-ylpropanenitrile Chemical compound C(CCC)OC(C#N)(CN1C=NC=C1)C1=C(C=C(C=C1)Cl)Cl SXXFKLQXHTWSLT-UHFFFAOYSA-N 0.000 claims 2
- HPUFKQJSHDRFCT-UHFFFAOYSA-N 2-butoxy-2-(2-chlorophenyl)-3-imidazol-1-ylpropanenitrile Chemical compound C(CCC)OC(C#N)(CN1C=NC=C1)C1=C(C=CC=C1)Cl HPUFKQJSHDRFCT-UHFFFAOYSA-N 0.000 claims 2
- BLTPCAGRXYBKBL-UHFFFAOYSA-N 2-butoxy-2-(4-chlorophenyl)-3-imidazol-1-ylpropanenitrile Chemical compound C(CCC)OC(C#N)(CN1C=NC=C1)C1=CC=C(C=C1)Cl BLTPCAGRXYBKBL-UHFFFAOYSA-N 0.000 claims 2
- ZZCFGPGDSCFHAL-UHFFFAOYSA-N 2-decoxy-3-imidazol-1-yl-2-(2-methylphenyl)propanenitrile Chemical compound C(CCCCCCCCC)OC(C#N)(CN1C=NC=C1)C1=C(C=CC=C1)C ZZCFGPGDSCFHAL-UHFFFAOYSA-N 0.000 claims 2
- AQINEKJAVBYLAE-UHFFFAOYSA-N 3-imidazol-1-yl-2-(2-methoxyethoxy)-2-phenylpropanenitrile Chemical compound N1(C=NC=C1)CC(C#N)(C1=CC=CC=C1)OCCOC AQINEKJAVBYLAE-UHFFFAOYSA-N 0.000 claims 2
- DFEVRVBTBYAOFJ-UHFFFAOYSA-N 3-imidazol-1-yl-2-(2-methylphenyl)-2-propoxypropanenitrile Chemical compound N1(C=NC=C1)CC(C#N)(OCCC)C1=C(C=CC=C1)C DFEVRVBTBYAOFJ-UHFFFAOYSA-N 0.000 claims 2
- DJJWLXYNSBDQST-UHFFFAOYSA-N 3-imidazol-1-yl-2-methoxy-2-phenylpropanenitrile Chemical compound N1(C=NC=C1)CC(C#N)(C1=CC=CC=C1)OC DJJWLXYNSBDQST-UHFFFAOYSA-N 0.000 claims 2
- CWJOFQYKXURZPD-UHFFFAOYSA-N 3-imidazol-1-yl-2-phenyl-2-propan-2-yloxypropanenitrile Chemical compound N1(C=NC=C1)CC(C#N)(C1=CC=CC=C1)OC(C)C CWJOFQYKXURZPD-UHFFFAOYSA-N 0.000 claims 2
- 239000000645 desinfectant Substances 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- NRLBEURZDFMYRZ-UHFFFAOYSA-N 2-(2,2-dimethylpropoxy)-3-imidazol-1-yl-2-phenylpropanenitrile Chemical compound CC(COC(C#N)(CN1C=NC=C1)C1=CC=CC=C1)(C)C NRLBEURZDFMYRZ-UHFFFAOYSA-N 0.000 claims 1
- PYSFKXJAIIOYLS-UHFFFAOYSA-N 2-(2-fluorophenyl)-3-imidazol-1-yl-2-methoxypropanenitrile Chemical compound FC1=C(C=CC=C1)C(C#N)(CN1C=NC=C1)OC PYSFKXJAIIOYLS-UHFFFAOYSA-N 0.000 claims 1
- QQNHCZIGWBBLQL-UHFFFAOYSA-N 2-(3,3-dimethylbutoxy)-3-imidazol-1-yl-2-phenylpropanenitrile Chemical compound CC(CCOC(C#N)(CN1C=NC=C1)C1=CC=CC=C1)(C)C QQNHCZIGWBBLQL-UHFFFAOYSA-N 0.000 claims 1
- IBUMNFDIGVZWDH-UHFFFAOYSA-N 2-(3-chlorophenyl)-2-hexoxy-3-imidazol-1-ylpropanenitrile Chemical compound ClC=1C=C(C=CC1)C(C#N)(CN1C=NC=C1)OCCCCCC IBUMNFDIGVZWDH-UHFFFAOYSA-N 0.000 claims 1
- RAUDZLPXDQFPGU-UHFFFAOYSA-N 2-(4-bromophenyl)-2-hexoxy-3-imidazol-1-ylpropanenitrile Chemical compound BrC1=CC=C(C=C1)C(C#N)(CN1C=NC=C1)OCCCCCC RAUDZLPXDQFPGU-UHFFFAOYSA-N 0.000 claims 1
- HKKOPCZNFGRXTO-UHFFFAOYSA-N 2-butoxy-2-(2-fluorophenyl)-3-imidazol-1-ylpropanenitrile Chemical compound C(CCC)OC(C#N)(CN1C=NC=C1)C1=C(C=CC=C1)F HKKOPCZNFGRXTO-UHFFFAOYSA-N 0.000 claims 1
- NMXCAXXRVNUMHY-UHFFFAOYSA-N 2-butoxy-2-(3-chlorophenyl)-3-imidazol-1-ylpropanenitrile Chemical compound C(CCC)OC(C#N)(CN1C=NC=C1)C1=CC(=CC=C1)Cl NMXCAXXRVNUMHY-UHFFFAOYSA-N 0.000 claims 1
- MKEOHHBMCANQJN-UHFFFAOYSA-N 2-butoxy-3-imidazol-1-yl-2-(4-methoxyphenyl)propanenitrile Chemical compound C(CCC)OC(C#N)(CN1C=NC=C1)C1=CC=C(C=C1)OC MKEOHHBMCANQJN-UHFFFAOYSA-N 0.000 claims 1
- KUJLYZVVXVOUGR-UHFFFAOYSA-N 2-decoxy-3-imidazol-1-yl-2-phenylpropanenitrile Chemical compound C(CCCCCCCCC)OC(C#N)(CN1C=NC=C1)C1=CC=CC=C1 KUJLYZVVXVOUGR-UHFFFAOYSA-N 0.000 claims 1
- PWTAMGSKOXKQBF-UHFFFAOYSA-N 2-ethoxy-2-(2-fluorophenyl)-3-imidazol-1-ylpropanenitrile Chemical compound C(C)OC(C#N)(CN1C=NC=C1)C1=C(C=CC=C1)F PWTAMGSKOXKQBF-UHFFFAOYSA-N 0.000 claims 1
- GARTXNUPFOHZNK-UHFFFAOYSA-N 2-ethoxy-2-(4-fluorophenyl)-3-imidazol-1-ylpropanenitrile Chemical compound C(C)OC(C#N)(CN1C=NC=C1)C1=CC=C(C=C1)F GARTXNUPFOHZNK-UHFFFAOYSA-N 0.000 claims 1
- IHPVXFFLLSNOFY-UHFFFAOYSA-N 2-ethoxy-3-imidazol-1-yl-2-phenylpropanenitrile Chemical compound C(C)OC(C#N)(CN1C=NC=C1)C1=CC=CC=C1 IHPVXFFLLSNOFY-UHFFFAOYSA-N 0.000 claims 1
- AKZCIPDLNJSCLP-UHFFFAOYSA-N 3-imidazol-1-yl-2-(2-methylphenyl)-2-octoxypropanenitrile Chemical compound N1(C=NC=C1)CC(C#N)(OCCCCCCCC)C1=C(C=CC=C1)C AKZCIPDLNJSCLP-UHFFFAOYSA-N 0.000 claims 1
- OICMABPKVBEMCE-UHFFFAOYSA-N 3-imidazol-1-yl-2-octoxy-2-phenylpropanenitrile Chemical compound N1(C=NC=C1)CC(C#N)(C1=CC=CC=C1)OCCCCCCCC OICMABPKVBEMCE-UHFFFAOYSA-N 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 239000003899 bactericide agent Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 44
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- 230000008018 melting Effects 0.000 description 37
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- 239000013543 active substance Substances 0.000 description 26
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- 235000007340 Hordeum vulgare Nutrition 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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- 229940079593 drug Drugs 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
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- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 5
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- LQULPJYCKAPLGK-UHFFFAOYSA-N 3-imidazol-1-yl-2-phenyl-2-propoxypropanenitrile Chemical compound N1(C=NC=C1)CC(C#N)(OCCC)C1=CC=CC=C1 LQULPJYCKAPLGK-UHFFFAOYSA-N 0.000 description 4
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- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 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
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon 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
-
- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3125780.1 | 1981-06-30 | ||
| DE19813125780 DE3125780A1 (de) | 1981-06-30 | 1981-06-30 | Imidazolyl-propionitrile, verfahren zur herstellung dieser verbindungen sowie diese enthaltende biozide mittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS588070A JPS588070A (ja) | 1983-01-18 |
| JPS6055070B2 true JPS6055070B2 (ja) | 1985-12-03 |
Family
ID=6135760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57106257A Expired JPS6055070B2 (ja) | 1981-06-30 | 1982-06-22 | イミダゾリル−プロピオニトリル、その製造法及び該化合物を含有する殺菌剤 |
Country Status (37)
| Country | Link |
|---|---|
| JP (1) | JPS6055070B2 (xx) |
| KR (1) | KR840000506A (xx) |
| AR (1) | AR231440A1 (xx) |
| AT (1) | ATA247082A (xx) |
| AU (1) | AU8546482A (xx) |
| BE (1) | BE893696A (xx) |
| BG (1) | BG37373A3 (xx) |
| BR (1) | BR8203803A (xx) |
| CA (1) | CA1186317A (xx) |
| CH (1) | CH655311A5 (xx) |
| CS (1) | CS236480B2 (xx) |
| DD (1) | DD202977A5 (xx) |
| DE (1) | DE3125780A1 (xx) |
| DK (1) | DK291582A (xx) |
| ES (1) | ES8304092A1 (xx) |
| FI (1) | FI822033L (xx) |
| FR (1) | FR2519635A1 (xx) |
| GB (1) | GB2101995B (xx) |
| GR (1) | GR81396B (xx) |
| HU (1) | HU189598B (xx) |
| IL (1) | IL66164A (xx) |
| IT (1) | IT1151802B (xx) |
| LU (1) | LU84246A1 (xx) |
| MA (1) | MA19512A1 (xx) |
| NL (1) | NL8202339A (xx) |
| NO (1) | NO822231L (xx) |
| NZ (1) | NZ200967A (xx) |
| PH (1) | PH19047A (xx) |
| PL (1) | PL129716B1 (xx) |
| PT (1) | PT75147B (xx) |
| RO (1) | RO85277B (xx) |
| SE (1) | SE8204027L (xx) |
| SU (2) | SU1245251A3 (xx) |
| TR (1) | TR21402A (xx) |
| YU (1) | YU125882A (xx) |
| ZA (1) | ZA824688B (xx) |
| ZW (1) | ZW13182A1 (xx) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63120362U (xx) * | 1987-01-28 | 1988-08-04 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3329213A1 (de) * | 1983-08-10 | 1985-02-21 | Schering AG, 1000 Berlin und 4709 Bergkamen | Azolyl-propannitrile, verfahren zur herstellung dieser verbindungen sowie diese enthaltende biozide mittel |
| DE3644616A1 (de) * | 1986-12-29 | 1988-07-07 | Lentia Gmbh | Imidazolderivate, verfahren zur herstellung und deren verwendung |
| JPH0624355U (ja) * | 1991-07-12 | 1994-03-29 | 株式会社三輝産業 | バッテリーチャージャ |
| USD872768S1 (en) | 2016-02-19 | 2020-01-14 | Sony Corporation | Robot having display screen with animated graphical user interface |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4167576A (en) * | 1977-10-06 | 1979-09-11 | Rohm And Haas Company | Cyanoaralkylheterocyclic compounds |
| DE3175673D1 (en) * | 1980-11-19 | 1987-01-15 | Ici Plc | Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them |
-
1981
- 1981-06-30 DE DE19813125780 patent/DE3125780A1/de not_active Withdrawn
-
1982
- 1982-05-14 PH PH27307A patent/PH19047A/en unknown
- 1982-06-08 FI FI822033A patent/FI822033L/fi not_active Application Discontinuation
- 1982-06-09 NL NL8202339A patent/NL8202339A/xx not_active Application Discontinuation
- 1982-06-09 ES ES512949A patent/ES8304092A1/es not_active Expired
- 1982-06-10 YU YU01258/82A patent/YU125882A/xx unknown
- 1982-06-10 CS CS824318A patent/CS236480B2/cs unknown
- 1982-06-15 NZ NZ200967A patent/NZ200967A/en unknown
- 1982-06-18 IT IT21939/82A patent/IT1151802B/it active
- 1982-06-18 RO RO107928A patent/RO85277B/ro unknown
- 1982-06-22 JP JP57106257A patent/JPS6055070B2/ja not_active Expired
- 1982-06-24 MA MA19719A patent/MA19512A1/fr unknown
- 1982-06-24 BG BG8257133A patent/BG37373A3/xx unknown
- 1982-06-25 AT AT0247082A patent/ATA247082A/de not_active Application Discontinuation
- 1982-06-25 SU SU823456292A patent/SU1245251A3/ru active
- 1982-06-25 SU SU823456111A patent/SU1114334A3/ru active
- 1982-06-28 GR GR68583A patent/GR81396B/el unknown
- 1982-06-28 PL PL1982237145A patent/PL129716B1/pl unknown
- 1982-06-28 CH CH3960/82A patent/CH655311A5/de not_active IP Right Cessation
- 1982-06-28 FR FR8211287A patent/FR2519635A1/fr active Granted
- 1982-06-28 TR TR21402A patent/TR21402A/xx unknown
- 1982-06-29 CA CA000406258A patent/CA1186317A/en not_active Expired
- 1982-06-29 PT PT75147A patent/PT75147B/pt unknown
- 1982-06-29 GB GB08218796A patent/GB2101995B/en not_active Expired
- 1982-06-29 DK DK291582A patent/DK291582A/da not_active Application Discontinuation
- 1982-06-29 NO NO822231A patent/NO822231L/no unknown
- 1982-06-29 BR BR8203803A patent/BR8203803A/pt unknown
- 1982-06-29 HU HU822103A patent/HU189598B/hu unknown
- 1982-06-29 BE BE0/208488A patent/BE893696A/fr not_active IP Right Cessation
- 1982-06-29 SE SE8204027A patent/SE8204027L/xx not_active Application Discontinuation
- 1982-06-29 IL IL66164A patent/IL66164A/xx unknown
- 1982-06-30 ZW ZW131/82A patent/ZW13182A1/xx unknown
- 1982-06-30 AR AR289853A patent/AR231440A1/es active
- 1982-06-30 LU LU84246A patent/LU84246A1/de unknown
- 1982-06-30 KR KR1019820002943A patent/KR840000506A/ko unknown
- 1982-06-30 DD DD82241259A patent/DD202977A5/de unknown
- 1982-06-30 ZA ZA824688A patent/ZA824688B/xx unknown
- 1982-06-30 AU AU85464/82A patent/AU8546482A/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63120362U (xx) * | 1987-01-28 | 1988-08-04 |
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