LU85237A1 - Nouveaux derives de l'ethanol,leur preparation et leur utilisation comme fongicides - Google Patents
Nouveaux derives de l'ethanol,leur preparation et leur utilisation comme fongicides Download PDFInfo
- Publication number
- LU85237A1 LU85237A1 LU85237A LU85237A LU85237A1 LU 85237 A1 LU85237 A1 LU 85237A1 LU 85237 A LU85237 A LU 85237A LU 85237 A LU85237 A LU 85237A LU 85237 A1 LU85237 A1 LU 85237A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- group
- compound according
- substituted
- acceptable
- halogen
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims description 7
- 239000000417 fungicide Substances 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 93
- 239000000203 mixture Substances 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical group 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 15
- 230000000855 fungicidal effect Effects 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 14
- 150000004696 coordination complex Chemical class 0.000 claims description 13
- -1 2-Caryl Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 claims description 9
- 101100495925 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr3 gene Proteins 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 9
- 241000233866 Fungi Species 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 7
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 150000002170 ethers Chemical class 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000011149 active material Substances 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 230000003032 phytopathogenic effect Effects 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 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 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims 1
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 241000220225 Malus Species 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 241000221785 Erysiphales Species 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 235000021016 apples Nutrition 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 240000007154 Coffea arabica Species 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- QKCYUBJJPXLRFJ-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-cyclopropylethanone Chemical compound C1=CC(Cl)=CC=C1C(=O)CC1CC1 QKCYUBJJPXLRFJ-UHFFFAOYSA-N 0.000 description 3
- 241000235349 Ascomycota Species 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
- 241000221787 Erysiphe Species 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 206010017533 Fungal infection Diseases 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 208000031888 Mycoses Diseases 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- 241000219094 Vitaceae Species 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 235000021021 grapes Nutrition 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 241000221198 Basidiomycota Species 0.000 description 2
- 235000009849 Cucumis sativus Nutrition 0.000 description 2
- 241001181537 Hemileia Species 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000896238 Oidium Species 0.000 description 2
- 241000896242 Podosphaera Species 0.000 description 2
- 241000221300 Puccinia Species 0.000 description 2
- 241000221535 Pucciniales Species 0.000 description 2
- 241000510929 Uncinula Species 0.000 description 2
- 241000221576 Uromyces Species 0.000 description 2
- 241000221577 Uromyces appendiculatus Species 0.000 description 2
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- MZMJHXFYLRTLQX-UHFFFAOYSA-N ethenylsulfinylbenzene Chemical compound C=CS(=O)C1=CC=CC=C1 MZMJHXFYLRTLQX-UHFFFAOYSA-N 0.000 description 2
- 150000003944 halohydrins Chemical class 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 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 2
- 229960004125 ketoconazole Drugs 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- SVSQETXNYGNLQB-UHFFFAOYSA-N (4-chlorophenyl)-(1-cyclopropylcyclopropyl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1(C2CC2)CC1 SVSQETXNYGNLQB-UHFFFAOYSA-N 0.000 description 1
- PEUPUKDBCPLDIH-UHFFFAOYSA-N 1,2,4-triazole Chemical group C1=NC=N[N]1 PEUPUKDBCPLDIH-UHFFFAOYSA-N 0.000 description 1
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
- WAKBGVGRUCMZFV-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-cyclopropyl-2-methylpropan-1-one Chemical compound C=1C=C(Cl)C=CC=1C(=O)C(C)(C)C1CC1 WAKBGVGRUCMZFV-UHFFFAOYSA-N 0.000 description 1
- SZIBSUZUPGRNEE-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-3-cyclopropyl-2-methoxy-3-methylbutyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=CC=1C(C(C)(C)C1CC1)(OC)CN1C=NC=N1 SZIBSUZUPGRNEE-UHFFFAOYSA-N 0.000 description 1
- 125000006451 1-cyclopropyl cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
- HVCFCNAITDHQFX-UHFFFAOYSA-N 1-cyclopropylethanone Chemical compound CC(=O)C1CC1 HVCFCNAITDHQFX-UHFFFAOYSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- KJWHJDGMOQJLGF-UHFFFAOYSA-N 1-methylsulfanyldodecane Chemical compound CCCCCCCCCCCCSC KJWHJDGMOQJLGF-UHFFFAOYSA-N 0.000 description 1
- PTMRDOLOEDPHLB-UHFFFAOYSA-N 2,3-dipentylphenol Chemical compound CCCCCC1=CC=CC(O)=C1CCCCC PTMRDOLOEDPHLB-UHFFFAOYSA-N 0.000 description 1
- AIUIVRDVAUOQOO-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(1-cyclopropylcyclopropyl)oxirane Chemical compound C1=CC(Cl)=CC=C1C1(C2(CC2)C2CC2)OC1 AIUIVRDVAUOQOO-UHFFFAOYSA-N 0.000 description 1
- QKTOXOPFYCOLPV-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(1-cyclopropylethyl)oxirane Chemical compound C1OC1(C=1C=CC(Cl)=CC=1)C(C)C1CC1 QKTOXOPFYCOLPV-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- FIEMNCUPUKWJBC-UHFFFAOYSA-N 2-methylprop-1-ene-1-thiol Chemical class CC(C)=CS FIEMNCUPUKWJBC-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- ZIOLCZCJJJNOEJ-UHFFFAOYSA-N 2-pyrrol-1-ylethanol Chemical class OCCN1C=CC=C1 ZIOLCZCJJJNOEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- CDIJOYCNNFLOAX-UHFFFAOYSA-N 4-(trichloromethylsulfanyl)isoindole-1,3-dione Chemical class ClC(Cl)(Cl)SC1=CC=CC2=C1C(=O)NC2=O CDIJOYCNNFLOAX-UHFFFAOYSA-N 0.000 description 1
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
- IVYMIRMKXZAHRV-UHFFFAOYSA-N 4-chlorophenylacetonitrile Chemical compound ClC1=CC=C(CC#N)C=C1 IVYMIRMKXZAHRV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 241000207875 Antirrhinum Species 0.000 description 1
- 240000007087 Apium graveolens Species 0.000 description 1
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 1
- 235000010591 Appio Nutrition 0.000 description 1
- 241001480043 Arthrodermataceae Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000895523 Blumeria graminis f. sp. hordei Species 0.000 description 1
- 241000895502 Blumeria graminis f. sp. tritici Species 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101100240528 Caenorhabditis elegans nhr-23 gene Proteins 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241001529717 Corticium <basidiomycota> Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 241000510928 Erysiphe necator Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 241000208150 Geraniaceae Species 0.000 description 1
- 241000208152 Geranium Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 239000005802 Mancozeb Substances 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 101100062121 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cyc-1 gene Proteins 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241001503951 Phoma Species 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 241000319939 Pleosporales Species 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 239000005822 Propiconazole Substances 0.000 description 1
- 241000231139 Pyricularia Species 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- 239000006004 Quartz sand Substances 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- 241000813090 Rhizoctonia solani Species 0.000 description 1
- 241000109329 Rosa xanthina Species 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 241001533598 Septoria Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 241000222646 Stereum Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 241000865903 Thielaviopsis Species 0.000 description 1
- 244000301083 Ustilago maydis Species 0.000 description 1
- 235000015919 Ustilago maydis Nutrition 0.000 description 1
- 201000007096 Vulvovaginal Candidiasis Diseases 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- RKGQARHDBPDJGV-UHFFFAOYSA-N [2-(4-chlorophenyl)-3-cyclopropyl-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-yl] acetate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)(C)C1CC1)(OC(=O)C)CN1C=NC=N1 RKGQARHDBPDJGV-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000037304 dermatophytes Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- UJTPZISIAWDGFF-UHFFFAOYSA-N ethenylsulfonylbenzene Chemical compound C=CS(=O)(=O)C1=CC=CC=C1 UJTPZISIAWDGFF-UHFFFAOYSA-N 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 239000002038 ethyl acetate fraction Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000002044 hexane fraction Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229920000940 maneb Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 235000021018 plums Nutrition 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000001022 rhodamine dye Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
- A01N43/64—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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pest Control & Pesticides (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Agronomy & Crop Science (AREA)
- General Chemical & Material Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (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 |
|---|---|---|---|
| CH119683 | 1983-03-04 | ||
| CH1196/83A CH658654A5 (de) | 1983-03-04 | 1983-03-04 | Azolderivate, verfahren zu ihrer herstellung und mittel die diese verbindungen enthalten. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU85237A1 true LU85237A1 (fr) | 1984-11-14 |
Family
ID=4204755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU85237A LU85237A1 (fr) | 1983-03-04 | 1984-03-02 | Nouveaux derives de l'ethanol,leur preparation et leur utilisation comme fongicides |
Country Status (35)
Families Citing this family (94)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH658654A5 (de) * | 1983-03-04 | 1986-11-28 | Sandoz Ag | Azolderivate, verfahren zu ihrer herstellung und mittel die diese verbindungen enthalten. |
| NL8402548A (nl) * | 1983-09-01 | 1985-04-01 | Sandoz Ag | Nieuwe azoolverbindingen. |
| CH668772A5 (de) * | 1984-07-13 | 1989-01-31 | Sandoz Ag | 1,2,4-triazol-derivat, verfahren zu dessen herstellung und seine verwendung. |
| EP0180850A3 (de) * | 1984-11-02 | 1987-05-27 | Bayer Ag | Antimykotische Azolylmethyl-cyclopropyl-carbinol Derivate |
| CN1008735B (zh) * | 1984-11-02 | 1990-07-11 | 拜尔公司 | 以取代的氮杂茂基甲基-环丙基-甲醇衍生物为活性成分的组合物 |
| GB8429932D0 (en) * | 1984-11-27 | 1985-01-03 | Pfizer Ltd | Triazole antifungal agents |
| GB8614367D0 (en) * | 1986-06-12 | 1986-07-16 | Sandoz Ltd | Fungicides |
| GB8617780D0 (en) * | 1986-07-21 | 1986-08-28 | Sandoz Ltd | Fungicides |
| GB8629360D0 (en) * | 1986-12-09 | 1987-01-21 | Sandoz Ltd | Fungicides |
| FR2609368B1 (fr) * | 1987-01-14 | 1990-04-13 | Sandoz Sa Produits | Utilisation de derives du 1, 2, 4-triazole pour combattre les maladies de plaies de taille des plantes perennes |
| DE3800094C2 (de) * | 1987-01-14 | 1998-05-14 | Ciba Geigy Ag | Verfahren und hydrophobe Zubereitung zur Bekämpfung von Schnittwundparasiten bei Pflanzen |
| CA1304938C (en) * | 1987-03-19 | 1992-07-14 | Tsugio Kawahara | Display apparatus for an automatic vending machine |
| DE3732388A1 (de) * | 1987-09-25 | 1989-04-06 | Bayer Ag | Azolylmethylcyclopropyl-carbinole enthaltende antimykotische mittel |
| DE3732387A1 (de) * | 1987-09-25 | 1989-04-06 | Bayer Ag | Azolylmethylcyclopropyl-derivate enthaltende antimykotische mittel |
| IT1232943B (it) * | 1987-11-09 | 1992-03-10 | Mini Ricerca Scient Tecnolog | Azolilderivati fungicidi. |
| US5219876A (en) * | 1987-12-02 | 1993-06-15 | Sandoz Ltd. | Substituted-cyano-2-[4-(phenyl-ethynyl)phenyl]-1-1 (1H-1,2,4-triazol-1-yl)ethane derivatives |
| GB8729107D0 (en) * | 1987-12-14 | 1988-01-27 | Ici Plc | Chemical process |
| NO171272C (no) * | 1988-03-04 | 1993-02-17 | Sankyo Co | Analogifremgangsmaate til fremstilling av terapeutisk aktive 1,2,4-triazolforbindelser |
| BE1001499A5 (fr) * | 1988-07-14 | 1989-11-14 | Sandoz Sa | Procede pour combattre les maladies de plaies de taille des plantes perennes. |
| DE3834875A1 (de) * | 1988-10-13 | 1990-04-19 | Sandoz Ag | Staubfreie zusammensetzungen |
| MX26077A (es) | 1990-06-05 | 1993-10-01 | Ciba Geigy Ag | Esteres de oxima y procedimiento para su preparacion |
| ES2084140T3 (es) | 1990-11-02 | 1996-05-01 | Ciba Geigy Ag | Agentes fungicidas. |
| US5156832A (en) * | 1991-03-18 | 1992-10-20 | Sandoz Ltd. | Compositions containing cyproconazole and rose bengal |
| ATE136728T1 (de) * | 1991-12-19 | 1996-05-15 | Ciba Geigy Ag | Mikrobizide |
| US6423732B1 (en) * | 1992-02-04 | 2002-07-23 | Syngenta Participations Ag | Synergistic combinations of cyproconazole |
| GB9202378D0 (en) * | 1992-02-05 | 1992-03-18 | Sandoz Ltd | Inventions relating to fungicidal compositions |
| ATE160483T1 (de) * | 1992-02-13 | 1997-12-15 | Ciba Geigy Ag | Fungizide mischungen auf der basis von triazol- fungiziden und 4,6-dimethyl-n-phenyl-2- pyrimidinamin |
| DE4325517A1 (de) * | 1992-07-31 | 1994-02-03 | Shell Int Research | Fungizide Zusammensetzungen |
| USH1400H (en) * | 1992-08-11 | 1995-01-03 | Culbreath; Albert K. | Fungicide |
| DE4233337A1 (de) * | 1992-10-05 | 1994-04-07 | Bayer Ag | Mikrobizide Mittel |
| US5342980A (en) | 1992-12-30 | 1994-08-30 | American Cyanamid Company | Fungicidal agents |
| DK0645091T3 (da) * | 1993-09-24 | 1996-05-13 | Basf Ag | Fungicide blandinger |
| CA2294332C (en) | 1997-06-30 | 2008-08-26 | Monsanto Company | Microparticles containing agricultural active ingredients |
| EP1239733B1 (de) * | 1999-12-13 | 2003-07-02 | Bayer CropScience AG | Fungizide wirkstoffkombinationen |
| DE10019758A1 (de) | 2000-04-20 | 2001-10-25 | Bayer Ag | Fungizide Wirkstoffkombinationen |
| DE10103832A1 (de) * | 2000-05-11 | 2001-11-15 | Bayer Ag | Fungizide Wirkstoffkombinationen |
| DE10141618A1 (de) * | 2001-08-24 | 2003-03-06 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
| SI1484975T1 (sl) * | 2002-03-07 | 2007-10-31 | Basf Ag | Fungicidne meĺ anice na osnovi triazolov |
| KR20040097274A (ko) * | 2002-04-05 | 2004-11-17 | 바스프 악티엔게젤샤프트 | 벤즈아미독심 유도체 및 아졸 기재 살진균제 혼합물 |
| DE10347090A1 (de) | 2003-10-10 | 2005-05-04 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE10349501A1 (de) * | 2003-10-23 | 2005-05-25 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| CN1886047A (zh) * | 2003-11-27 | 2006-12-27 | 巴斯福股份公司 | 基于三唑并嘧啶衍生物和康唑(conazole)的杀真菌混合物 |
| EP2255629A3 (de) | 2004-04-30 | 2012-09-19 | Basf Se | Fungizide Mischungen |
| DE102004049761A1 (de) * | 2004-10-12 | 2006-04-13 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
| DE102005015677A1 (de) * | 2005-04-06 | 2006-10-12 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| EP2255648A3 (de) | 2005-06-09 | 2011-03-02 | Bayer CropScience AG | Wirkstoffkombinationen |
| DE102005026482A1 (de) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Wirkstoffkombinationen |
| DE102005035300A1 (de) | 2005-07-28 | 2007-02-01 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE102006023263A1 (de) | 2006-05-18 | 2007-11-22 | Bayer Cropscience Ag | Synergistische Wirkstoffkombinationen |
| CA2661170A1 (en) | 2006-09-18 | 2008-03-27 | Basf Se | Pesticidal mixtures |
| US7772156B2 (en) * | 2006-11-01 | 2010-08-10 | Buckman Laboratories International, Inc. | Microbicidal compositions including a cyanodithiocarbimate and a second microbicide, and methods of using the same |
| EP2258177A3 (en) | 2006-12-15 | 2011-11-09 | Rohm and Haas Company | Mixtures comprising 1-methylcyclopropene |
| EP2109366A2 (en) | 2007-02-06 | 2009-10-21 | Basf Se | Pesticidal mixtures |
| EA017621B1 (ru) | 2007-04-23 | 2013-01-30 | Басф Се | Повышение продуктивности растений путем комбинирования химических веществ с трансгенными модификациями |
| EP2000028A1 (de) * | 2007-06-06 | 2008-12-10 | Bayer CropScience Aktiengesellschaft | Fungizide Wirkstoffkombinationen |
| US8349877B2 (en) | 2007-09-26 | 2013-01-08 | Basf Se | Ternary fungicidal compositions comprising boscalid and chlorothalonil |
| DE102007045920B4 (de) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Synergistische Wirkstoffkombinationen |
| MX2011009732A (es) | 2009-03-25 | 2011-09-29 | Bayer Cropscience Ag | Combinaciones de principios activos sinergicas. |
| CN101565406B (zh) * | 2009-04-29 | 2010-11-10 | 江苏七洲绿色化工股份有限公司 | 环唑醇的制备工艺 |
| EP2440535A1 (en) | 2009-06-12 | 2012-04-18 | Basf Se | Antifungal 1,2,4-triazolyl derivatives having a 5- sulfur substituent |
| CN104430378A (zh) * | 2009-07-16 | 2015-03-25 | 拜尔农作物科学股份公司 | 含苯基三唑的协同活性物质结合物 |
| WO2011026796A1 (en) | 2009-09-01 | 2011-03-10 | Basf Se | Synergistic fungicidal mixtures comprising lactylates and method for combating phytopathogenic fungi |
| CN101786948B (zh) * | 2010-01-25 | 2013-01-30 | 江苏省农用激素工程技术研究中心有限公司 | 1-（4-氯苯基）-2-环丙基-1-丙酮的制备方法 |
| CN101857576B (zh) * | 2010-06-18 | 2012-07-25 | 中国科学院上海有机化学研究所 | 通过环丙基甲基酮制备环唑醇的方法 |
| EP2605656A1 (en) * | 2010-08-17 | 2013-06-26 | Bayer Intellectual Property GmbH | Use of n-phenylethylpyrazole carboxamide derivatives or salts thereof for controlling powdery mildew primary infections |
| AU2011347752A1 (en) | 2010-12-20 | 2013-07-11 | Basf Se | Pesticidal active mixtures comprising pyrazole compounds |
| EP2481284A3 (en) | 2011-01-27 | 2012-10-17 | Basf Se | Pesticidal mixtures |
| JP6049684B2 (ja) | 2011-03-23 | 2016-12-21 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | イミダゾリウム基を含むポリマーのイオン性化合物を含有する組成物 |
| WO2013030338A2 (en) | 2011-09-02 | 2013-03-07 | Basf Se | Agricultural mixtures comprising arylquinazolinone compounds |
| CN102349518B (zh) * | 2011-11-01 | 2013-05-15 | 海利尔药业集团股份有限公司 | 一种含有环唑醇和氟吗啉的杀菌组合物 |
| CN102584558B (zh) * | 2011-12-21 | 2013-10-30 | 湖南化工研究院 | 一种1-(4-氯苯基)-2-环丙基-1-丙酮的制备方法 |
| CN102584726B (zh) * | 2012-01-07 | 2014-05-14 | 浙江禾本科技有限公司 | 一种杀菌剂戊菌唑的制备方法 |
| BR122019015099B1 (pt) | 2012-06-20 | 2020-04-07 | Basf Se | mistura pesticida, composição, composição agrícola, métodos para o combate ou controle das pragas de invertebrados, para a proteção dos vegetais em crescimento ou dos materias de propagação vegetal, para a proteção de material de propagação vegetal e uso de uma mistura pesticida |
| US20150257383A1 (en) | 2012-10-12 | 2015-09-17 | Basf Se | Method for combating phytopathogenic harmful microbes on cultivated plants or plant propagation material |
| WO2014095381A1 (en) | 2012-12-19 | 2014-06-26 | Basf Se | Fungicidal imidazolyl and triazolyl compounds |
| CA2894264C (en) | 2012-12-20 | 2023-03-07 | BASF Agro B.V. | Compositions comprising a triazole compound |
| EP2783569A1 (en) | 2013-03-28 | 2014-10-01 | Basf Se | Compositions comprising a triazole compound |
| EP2835052A1 (en) | 2013-08-07 | 2015-02-11 | Basf Se | Fungicidal mixtures comprising pyrimidine fungicides |
| PL3041355T3 (pl) | 2013-09-03 | 2017-10-31 | Bayer Cropscience Ag | Zastosowanie grzybobójczych substancji czynnych do kontrolowania Chalara fraxinea w drzewostanie jesionu |
| CN105722833A (zh) | 2013-09-16 | 2016-06-29 | 巴斯夫欧洲公司 | 杀真菌的嘧啶化合物 |
| WO2015036059A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
| BR102013027313B1 (pt) * | 2013-10-23 | 2019-06-18 | Iharabras S.A. Indústrias Químicas | Processo para a preparação seletiva de (1h-1,2,4-triazol-1-il) alcanóis, composto hidrazinil alcanol obtido por tal processo e seu uso |
| MX2016012540A (es) * | 2014-03-26 | 2017-01-09 | Basf Se | Compuestos de [1,2,4]triazol e imidazol sustituidos, como fungicidas. |
| EP2979549A1 (en) | 2014-07-31 | 2016-02-03 | Basf Se | Method for improving the health of a plant |
| ES2774793T3 (es) | 2014-10-24 | 2020-07-22 | Basf Se | Partículas pesticidas orgánicas |
| CN105777508B (zh) * | 2014-12-22 | 2019-01-25 | 上海泰禾国际贸易有限公司 | 一种1-(4-氯苯基)-2-环丙基-1-丙酮的合成方法 |
| EP2910126A1 (en) | 2015-05-05 | 2015-08-26 | Bayer CropScience AG | Active compound combinations having insecticidal properties |
| ES2873388T3 (es) | 2015-07-02 | 2021-11-03 | Basf Agro Bv | Composiciones plaguicidas que comprenden un compuesto de triazol |
| EP3558304A2 (en) | 2016-12-23 | 2019-10-30 | Helmholtz Zentrum München - Deutsches Forschungszentrum für Gesundheit und Umwelt (GmbH) | Inhibitors of cytochrome p450 family 7 subfamily b member 1 (cyp7b1) for use in treating diseases |
| CN109020905B (zh) * | 2017-06-09 | 2022-12-23 | 华东理工大学 | 两种环丙唑醇的多晶型及其制备方法 |
| US11241417B2 (en) | 2018-06-21 | 2022-02-08 | Yumanity Therapeutics, Inc. | Compositions and methods for the treatment and prevention of neurological disorders |
| CN109006836A (zh) * | 2018-10-10 | 2018-12-18 | 江苏七洲绿色化工股份有限公司 | 一种含有环丙唑醇的干悬浮剂及其制备方法 |
| MX2022002846A (es) | 2019-09-12 | 2022-04-06 | Saltigo Gmbh | Procedimiento mejorado para la preparacion de epoxidos a partir de aldehidos o cetonas. |
| EP4028379A1 (de) | 2019-09-12 | 2022-07-20 | Saltigo GmbH | Verbessertes verfahren zur herstellung von cyclopropylverbindungen aus alkenen |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4654332A (en) * | 1979-03-07 | 1987-03-31 | Imperial Chemical Industries Plc | Heterocyclic compounds |
| IL60470A0 (en) * | 1979-07-04 | 1980-09-16 | Pfizer | Imidazole derivatives,their preparation and pharmaceutical compositions containing them |
| US4414210A (en) * | 1979-10-02 | 1983-11-08 | Rohm And Haas Company | 2-Hydroxyarylethyltriazole fungicides |
| DE3042303A1 (de) * | 1979-11-13 | 1981-08-27 | Sandoz-Patent-GmbH, 7850 Lörrach | Organische verbindungen, deren herstellung und verwendung |
| CH647513A5 (de) * | 1979-11-13 | 1985-01-31 | Sandoz Ag | Triazol-derivate, deren herstellung und verwendung. |
| US4366401A (en) * | 1979-12-01 | 1982-12-28 | Lucas Industries Limited | Electromagnetic devices |
| US4432989A (en) * | 1980-07-18 | 1984-02-21 | Sandoz, Inc. | αAryl-1H-imidazole-1-ethanols |
| EP0123160B1 (en) * | 1980-08-18 | 1992-10-28 | Zeneca Limited | Triazole compounds, a process for preparing them, their use as plant fungicides and plant growth regulators and compositions containing them |
| HU186341B (en) * | 1980-08-28 | 1985-07-29 | Ici Ltd | Pharmaceutical compositions of fungicide activity containing triazol derivatives |
| EP0052424B2 (en) * | 1980-11-19 | 1990-02-28 | Imperial Chemical Industries Plc | Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them |
| EP0117578A3 (en) * | 1983-02-23 | 1985-01-30 | Shionogi & Co., Ltd. | Azole-substituted alcohol derivatives |
| CH658654A5 (de) * | 1983-03-04 | 1986-11-28 | Sandoz Ag | Azolderivate, verfahren zu ihrer herstellung und mittel die diese verbindungen enthalten. |
| NL8402548A (nl) * | 1983-09-01 | 1985-04-01 | Sandoz Ag | Nieuwe azoolverbindingen. |
-
1983
- 1983-03-04 CH CH1196/83A patent/CH658654A5/de not_active IP Right Cessation
-
1984
- 1984-02-20 NL NLAANVRAGE8400529,A patent/NL189564C/xx not_active IP Right Cessation
- 1984-02-20 HU HU84655A patent/HU195907B/hu unknown
- 1984-02-27 FR FR8403095A patent/FR2542000B1/fr not_active Expired
- 1984-02-27 US US06/584,161 patent/US4664696A/en not_active Expired - Lifetime
- 1984-02-27 DE DE19843406993 patent/DE3406993A1/de active Granted
- 1984-02-27 BE BE1/10967A patent/BE899008A/fr not_active IP Right Cessation
- 1984-02-29 DK DK149684A patent/DK165407C/da not_active IP Right Cessation
- 1984-02-29 BR BR8400958A patent/BR8400958A/pt not_active IP Right Cessation
- 1984-02-29 GB GB08405226A patent/GB2136423B/en not_active Expired
- 1984-03-01 FI FI840824A patent/FI81784C/fi not_active IP Right Cessation
- 1984-03-01 ES ES530203A patent/ES530203A0/es active Granted
- 1984-03-02 CS CS841536A patent/CS251081B2/cs unknown
- 1984-03-02 CA CA000448704A patent/CA1232278A/en not_active Expired
- 1984-03-02 PL PL1984246493A patent/PL139662B1/pl unknown
- 1984-03-02 IT IT47791/84A patent/IT1199079B/it active
- 1984-03-02 SU SU843707140A patent/SU1416058A3/ru active
- 1984-03-02 UA UA3707140A patent/UA7048A1/uk unknown
- 1984-03-02 IL IL71126A patent/IL71126A/xx not_active IP Right Cessation
- 1984-03-02 PT PT78192A patent/PT78192B/pt unknown
- 1984-03-02 IE IE508/84A patent/IE57003B1/en not_active IP Right Cessation
- 1984-03-02 TR TR1540/84A patent/TR22432A/xx unknown
- 1984-03-02 JP JP59041207A patent/JPH06756B2/ja not_active Expired - Lifetime
- 1984-03-02 NZ NZ207359A patent/NZ207359A/xx unknown
- 1984-03-02 PH PH30333A patent/PH22915A/en unknown
- 1984-03-02 SE SE8401177A patent/SE456678B/sv not_active IP Right Cessation
- 1984-03-02 LU LU85237A patent/LU85237A1/fr unknown
- 1984-03-02 ZA ZA841606A patent/ZA841606B/xx unknown
- 1984-03-02 AU AU25253/84A patent/AU571490B2/en not_active Expired
- 1984-03-02 AT AT0071684A patent/AT387219B/de not_active IP Right Cessation
- 1984-03-03 EG EG149/84A patent/EG16963A/xx active
- 1984-03-09 DZ DZ847095A patent/DZ613A1/fr active
- 1984-03-21 GR GR74167A patent/GR82344B/el unknown
-
1987
- 1987-03-20 US US07/028,453 patent/US4849439A/en not_active Expired - Lifetime
- 1987-12-30 MY MY767/87A patent/MY8700767A/xx unknown
-
1988
- 1988-09-15 KE KE3832A patent/KE3832A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| LU85237A1 (fr) | Nouveaux derives de l'ethanol,leur preparation et leur utilisation comme fongicides | |
| BE898070A (fr) | Nouveaux derives de l'ethanol, leur preparation et leur utilisation comme fongicides. | |
| FR2612741A1 (fr) | Alpha-aryl-alpha-phenylethyl-1h-1,2,4-triazole-1-propanenitriles, composition fongicide les contenant, procede pour combattre les champignons phytopathogenes avec de tels nitriles et procede de preparation de ces nitriles | |
| FR2542315A1 (fr) | Nouveaux composes azoliques, leur preparation et leur utilisation comme antifongiques et fongicides | |
| FR2551438A1 (fr) | Nouveaux derives de l'ethanol, leur preparation et leur utilisation comme fongicides | |
| HU177167B (en) | Fungicide compositions and process for preparing 4-azolyl-4-phenoxy-butanoic acid derivatives as active substances thereof | |
| DK172423B1 (da) | Triazolderivater, farmaceutiske og landbrugsmæssige fungicide præparater indeholdende disse og fremgangsmåde til behandling | |
| BE886128A (fr) | Nouveaux derives du 1,2,4-triazole, leur preparation et leur utilisation comme agents fongicides | |
| EP0565463A1 (fr) | Dérivés triazole et imidazole fongicides | |
| EP0100193B1 (en) | Triazole anti-fungal agents | |
| EP1387837B1 (fr) | Nouveaux derives d'azole ou de triazole, leur procede de preparation et leur application comme medicaments anti-fongiques | |
| EP1272485A1 (fr) | Nouveaux derives de la 1,2,3,4-tetrahydroisoquinoleine, leur procede de preparation et leur application comme fongicides | |
| JPS6084284A (ja) | 抗真菌性トリアゾ−ル誘導体 | |
| FR2548665A1 (fr) | Nouveaux derives de l'ethanol, leur preparation et leur utilisation comme fongicides | |
| CA2054863A1 (fr) | Procede pour proteger les produits de multiplication des vegetaux a l'aide de triazolyl ou imidazolyl methylallyl alcool et composes nouveaux pour mettre en oeuvre le procede | |
| KR890003599B1 (ko) | 아졸 화합물의 제조방법 | |
| BE896914A (fr) | Derives triazolyles et leur applecation fongicide | |
| FR2606408A1 (fr) | Nouveau derive de l'ethanol, sa preparation et son utilisation comme fongicide | |
| LU86443A1 (fr) | Nouveaux compoes azoliques,leur preparation et leur utilisation comme antifongiques et fongicides | |
| EP0313984A1 (de) | Substituierte Azolylmethylcarbinole und diese enthaltende Arzneimittel | |
| JPH0288563A (ja) | 新規アリルアミノエチルアゾール | |
| LU86001A1 (fr) | Nouveau compose azolique,sa preparation et son utilisation comme antifongique et fongicide | |
| DE3406743A1 (de) | Neue 2,2-disubstituierte 1,3-dioxolane | |
| CS241098B2 (cs) | Způsob výroby nových bis-triazolových derivátů |