IL85800A - Imidazoles and triazoles are converted and used as fungicides - Google Patents
Imidazoles and triazoles are converted and used as fungicidesInfo
- Publication number
- IL85800A IL85800A IL8580088A IL8580088A IL85800A IL 85800 A IL85800 A IL 85800A IL 8580088 A IL8580088 A IL 8580088A IL 8580088 A IL8580088 A IL 8580088A IL 85800 A IL85800 A IL 85800A
- Authority
- IL
- Israel
- Prior art keywords
- dimethylsulphamoyl
- cyano
- optionally substituted
- imidazole
- group
- Prior art date
Links
- 239000000417 fungicide Substances 0.000 title description 6
- 150000002460 imidazoles Chemical class 0.000 title description 2
- 150000003852 triazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 71
- -1 sulphamoyl Chemical group 0.000 claims description 68
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
- 125000002252 acyl group Chemical group 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical group 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 241000233866 Fungi Species 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 230000000855 fungicidal effect Effects 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical group [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims description 3
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical group C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- MAPBOZIMPFVSNG-UHFFFAOYSA-N 2-cyano-n,n-dimethyl-4-(2-nitrophenyl)imidazole-1-sulfonamide Chemical compound N1=C(C#N)N(S(=O)(=O)N(C)C)C=C1C1=CC=CC=C1[N+]([O-])=O MAPBOZIMPFVSNG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- DSPLHMSZVNRSGD-UHFFFAOYSA-N 2-cyano-4-(2,4-dichlorophenyl)-n,n-dimethylimidazole-1-sulfonamide Chemical compound N1=C(C#N)N(S(=O)(=O)N(C)C)C=C1C1=CC=C(Cl)C=C1Cl DSPLHMSZVNRSGD-UHFFFAOYSA-N 0.000 claims 1
- REBWIJKRUDESCR-UHFFFAOYSA-N 2-cyano-n,n-dimethyl-4-(2,4,6-trichlorobenzoyl)imidazole-1-sulfonamide Chemical compound N1=C(C#N)N(S(=O)(=O)N(C)C)C=C1C(=O)C1=C(Cl)C=C(Cl)C=C1Cl REBWIJKRUDESCR-UHFFFAOYSA-N 0.000 claims 1
- NRWYOSJNEHUPDX-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-1-(dimethylsulfamoyl)imidazole-2-carbothioamide Chemical compound N1=C(C(N)=S)N(S(=O)(=O)N(C)C)C=C1C1=CC=C(Cl)C=C1Cl NRWYOSJNEHUPDX-UHFFFAOYSA-N 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- UPYDGXNGNRNQKT-UHFFFAOYSA-N n-[1-(dimethylsulfamoyl)-4-(2,3,4-trichlorophenyl)imidazole-2-carbothioyl]acetamide Chemical compound N1=C(C(=S)NC(C)=O)N(S(=O)(=O)N(C)C)C=C1C1=CC=C(Cl)C(Cl)=C1Cl UPYDGXNGNRNQKT-UHFFFAOYSA-N 0.000 claims 1
- 230000003032 phytopathogenic effect Effects 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
- 239000007858 starting material Substances 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- WTDHULULXKLSOZ-UHFFFAOYSA-N hydroxylamine hydrochloride Substances Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 5
- 238000010410 dusting Methods 0.000 description 5
- JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 241000813090 Rhizoctonia solani Species 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 230000008635 plant growth Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 3
- 241000227653 Lycopersicon Species 0.000 description 3
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000233679 Peronosporaceae Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 125000003435 aroyl group Chemical group 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 238000007333 cyanation reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 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 description 3
- 238000005406 washing Methods 0.000 description 3
- PYIWDZMUHRCEQH-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-n,n-dimethylimidazole-1-sulfonamide Chemical compound CN(C)S(=O)(=O)N1C=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 PYIWDZMUHRCEQH-UHFFFAOYSA-N 0.000 description 2
- LFQWPJPKLYXKEH-UHFFFAOYSA-N 5-(2-nitrophenyl)-1h-imidazole-2-carbonitrile Chemical compound [O-][N+](=O)C1=CC=CC=C1C1=CNC(C#N)=N1 LFQWPJPKLYXKEH-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 241000221787 Erysiphe Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- 241001330975 Magnaporthe oryzae Species 0.000 description 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
- QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000233622 Phytophthora infestans Species 0.000 description 2
- 206010039509 Scab Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
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- 150000002334 glycols Chemical class 0.000 description 2
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- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
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- BOSFFQYMAARUEJ-UHFFFAOYSA-N n,n-dimethyl-5-phenylimidazole-1-sulfonamide Chemical compound CN(C)S(=O)(=O)N1C=NC=C1C1=CC=CC=C1 BOSFFQYMAARUEJ-UHFFFAOYSA-N 0.000 description 1
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- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
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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
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- 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
- A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- 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
- A01N43/86—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/32—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing heterocyclic radicals
-
- 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
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878706779A GB8706779D0 (en) | 1987-03-21 | 1987-03-21 | Fungicides |
| GB878722329A GB8722329D0 (en) | 1987-09-22 | 1987-09-22 | Fungicides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL85800A0 IL85800A0 (en) | 1988-09-30 |
| IL85800A true IL85800A (en) | 1994-11-11 |
Family
ID=26292038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL8580088A IL85800A (en) | 1987-03-21 | 1988-03-21 | Imidazoles and triazoles are converted and used as fungicides |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0284277A1 (de) |
| JP (1) | JPS63255269A (de) |
| CN (1) | CN1027125C (de) |
| AU (1) | AU601558B2 (de) |
| BR (1) | BR8801269A (de) |
| CS (1) | CS273183B2 (de) |
| DK (1) | DK149288A (de) |
| FI (1) | FI881321A (de) |
| HU (1) | HU205537B (de) |
| IL (1) | IL85800A (de) |
| MA (1) | MA21226A1 (de) |
| MY (1) | MY103241A (de) |
| NZ (1) | NZ223958A (de) |
| PH (1) | PH24964A (de) |
| PT (1) | PT87010B (de) |
| TR (1) | TR24656A (de) |
| ZW (1) | ZW2588A1 (de) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1339133C (en) * | 1987-03-13 | 1997-07-29 | Rikuo Nasu | Imidazole compounds and biocidal composition comprising the same for controlling harmful organisms |
| DE3742716A1 (de) * | 1987-12-14 | 1989-06-22 | Schering Ag | Imidazolderivate ii |
| GB8906965D0 (en) * | 1989-03-28 | 1989-05-10 | Schering Agrochemicals Ltd | Fungicides |
| US5173503A (en) * | 1989-11-15 | 1992-12-22 | Schering Agrochemicals Limited | Imidazole fungicides |
| DE4004061A1 (de) * | 1990-02-10 | 1991-08-14 | Hoechst Ag | Neue imidazolverbindungen, verfahren zu deren herstellung, arzneimittel auf basis dieser verbindungen sowie einige zwischenprodukte |
| GB9014342D0 (en) * | 1990-06-27 | 1990-08-15 | Schering Agrochemicals Ltd | Fungicides |
| GB9023082D0 (en) * | 1990-10-24 | 1990-12-05 | Schering Agrochemicals Ltd | Fungicides |
| WO1992013451A1 (en) * | 1991-02-11 | 1992-08-20 | Schering Agrochemicals Limited | Imidazole pesticides |
| DE4139950A1 (de) * | 1991-12-04 | 1993-06-09 | Bayer Ag, 5090 Leverkusen, De | 2-cyanobenzimidazole, ein verfahren zu ihrer herstellung und ihre verwendung und neue vorprodukte |
| US5529686A (en) * | 1994-07-15 | 1996-06-25 | Minnesota Mining And Manufacturing Company | Composite membranes for solid phase extractions and reactions |
| DE19623207A1 (de) * | 1996-06-11 | 1997-12-18 | Bayer Ag | Imidazolderivate |
| AU8974598A (en) * | 1997-07-24 | 1999-02-16 | Bayer Aktiengesellschaft | Nitrophenyl-sulfonyl-imidazoles and use thereof for controlling vegetable and animal pests |
| ATE499365T1 (de) | 1997-10-24 | 2011-03-15 | Nissan Chemical Ind Ltd | Sulfamoyl-verbindungen und bakterizide für landwirtschaft oder gartenbau |
| DE19844497A1 (de) * | 1998-09-29 | 2000-03-30 | Bayer Ag | Sulfonyltriazol-Derivate |
| JP2001026506A (ja) * | 1999-04-28 | 2001-01-30 | Takeda Chem Ind Ltd | スルホンアミド誘導体 |
| CN110894190B (zh) * | 2018-09-13 | 2020-09-11 | 东莞市东阳光农药研发有限公司 | 三氮唑化合物及其在农业中的应用 |
| CN110396068B (zh) * | 2019-07-22 | 2023-01-20 | 昆明理工大学 | 4-邻烷氧芳基-1,2,3-三唑衍生物及合成方法和应用 |
| AU2021282645A1 (en) * | 2020-06-03 | 2023-01-19 | Ishihara Sangyo Kaisha, Ltd. | Antimicrobial agent for nonhuman animal |
| CN115996714A (zh) * | 2020-06-03 | 2023-04-21 | 石原产业株式会社 | 人用抗真菌剂 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2646143A1 (de) * | 1976-10-13 | 1978-04-20 | Bayer Ag | 4,5-dichlor-imidazol-1-carbonsaeure- arylester, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenschutzmittel |
| DE3628545A1 (de) * | 1985-09-23 | 1987-04-23 | Hoechst Ag | Arylmethylazole und deren salze, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung |
| JPS62221672A (ja) * | 1986-03-20 | 1987-09-29 | Nippon Tokushu Noyaku Seizo Kk | 新規スルホニルアゾ−ル |
| EP0246749A3 (de) * | 1986-05-17 | 1988-08-31 | AgrEvo UK Limited | Herbizide Triazole |
-
1988
- 1988-03-16 EP EP88302260A patent/EP0284277A1/de not_active Withdrawn
- 1988-03-18 JP JP63063720A patent/JPS63255269A/ja active Pending
- 1988-03-18 CS CS179988A patent/CS273183B2/cs unknown
- 1988-03-18 HU HU881367A patent/HU205537B/hu not_active IP Right Cessation
- 1988-03-18 DK DK149288A patent/DK149288A/da not_active Application Discontinuation
- 1988-03-18 MA MA21467A patent/MA21226A1/fr unknown
- 1988-03-18 PT PT87010A patent/PT87010B/pt not_active IP Right Cessation
- 1988-03-21 TR TR88/0209A patent/TR24656A/xx unknown
- 1988-03-21 BR BR8801269A patent/BR8801269A/pt not_active Application Discontinuation
- 1988-03-21 MY MYPI88000291A patent/MY103241A/en unknown
- 1988-03-21 PH PH36669A patent/PH24964A/en unknown
- 1988-03-21 AU AU13318/88A patent/AU601558B2/en not_active Ceased
- 1988-03-21 ZW ZW25/88A patent/ZW2588A1/xx unknown
- 1988-03-21 FI FI881321A patent/FI881321A/fi not_active Application Discontinuation
- 1988-03-21 CN CN88101622A patent/CN1027125C/zh not_active Expired - Fee Related
- 1988-03-21 NZ NZ223958A patent/NZ223958A/xx unknown
- 1988-03-21 IL IL8580088A patent/IL85800A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BR8801269A (pt) | 1988-10-25 |
| HU205537B (en) | 1992-05-28 |
| IL85800A0 (en) | 1988-09-30 |
| PT87010B (pt) | 1992-06-30 |
| MA21226A1 (fr) | 1988-10-01 |
| DK149288A (da) | 1988-09-22 |
| CN88101622A (zh) | 1988-10-05 |
| CN1027125C (zh) | 1994-12-28 |
| AU601558B2 (en) | 1990-09-13 |
| CS273183B2 (en) | 1991-03-12 |
| EP0284277A1 (de) | 1988-09-28 |
| PH24964A (en) | 1990-12-26 |
| ZW2588A1 (en) | 1988-10-26 |
| HUT49273A (en) | 1989-09-28 |
| JPS63255269A (ja) | 1988-10-21 |
| AU1331888A (en) | 1988-09-22 |
| NZ223958A (en) | 1989-11-28 |
| PT87010A (pt) | 1988-04-01 |
| CS179988A2 (en) | 1990-06-13 |
| FI881321A (fi) | 1988-09-22 |
| FI881321A0 (fi) | 1988-03-21 |
| DK149288D0 (da) | 1988-03-18 |
| TR24656A (tr) | 1992-01-09 |
| MY103241A (en) | 1993-05-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RH | Patent void |