JPH0526789B2 - - Google Patents
Info
- Publication number
- JPH0526789B2 JPH0526789B2 JP1899283A JP1899283A JPH0526789B2 JP H0526789 B2 JPH0526789 B2 JP H0526789B2 JP 1899283 A JP1899283 A JP 1899283A JP 1899283 A JP1899283 A JP 1899283A JP H0526789 B2 JPH0526789 B2 JP H0526789B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- following formula
- prepared
- hydrogen
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 212
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 164
- 239000000203 mixture Substances 0.000 claims description 84
- 238000000034 method Methods 0.000 claims description 75
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 64
- -1 haloalkylphenyl Chemical group 0.000 claims description 63
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 55
- 239000002904 solvent Substances 0.000 claims description 46
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 239000000126 substance Substances 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 25
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 150000002576 ketones Chemical class 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 19
- 150000004820 halides Chemical class 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 17
- 239000007818 Grignard reagent Substances 0.000 claims description 15
- 238000007363 ring formation reaction Methods 0.000 claims description 15
- 238000010561 standard procedure Methods 0.000 claims description 15
- 150000004795 grignard reagents Chemical class 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 229910052751 metal Chemical class 0.000 claims description 14
- 239000002184 metal Chemical class 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 230000000855 fungicidal effect Effects 0.000 claims description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 9
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 9
- 125000005059 halophenyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 239000011230 binding agent Substances 0.000 claims description 8
- 150000003852 triazoles Chemical class 0.000 claims description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 7
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 7
- 150000002009 diols Chemical class 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 150000003944 halohydrins Chemical class 0.000 claims description 7
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 7
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 claims description 6
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 150000002596 lactones Chemical class 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 5
- 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 claims description 5
- ZUZQHCXMXAUARS-UHFFFAOYSA-N 1-[[2-(4-chlorophenyl)-5-methyloxolan-2-yl]methyl]-1,2,4-triazole Chemical compound O1C(C)CCC1(C=1C=CC(Cl)=CC=1)CN1N=CN=C1 ZUZQHCXMXAUARS-UHFFFAOYSA-N 0.000 claims description 4
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 4
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 229940014800 succinic anhydride Drugs 0.000 claims description 4
- FEAUUPPHTWFZKK-UHFFFAOYSA-N 1-[[2-(2,4-dichlorophenyl)oxolan-2-yl]methyl]-1,2,4-triazole Chemical compound ClC1=CC(Cl)=CC=C1C1(CN2N=CN=C2)OCCC1 FEAUUPPHTWFZKK-UHFFFAOYSA-N 0.000 claims description 3
- NXELZCKGLDLVBH-UHFFFAOYSA-N 1-[[2-(4-chlorophenyl)-3-ethyloxolan-2-yl]methyl]-1,2,4-triazole Chemical compound CCC1CCOC1(C=1C=CC(Cl)=CC=1)CN1N=CN=C1 NXELZCKGLDLVBH-UHFFFAOYSA-N 0.000 claims description 3
- MQRHEDOAEMZEBK-UHFFFAOYSA-N 1-[[2-(4-chlorophenyl)-4,4-dimethyloxolan-2-yl]methyl]-1,2,4-triazole Chemical compound C1C(C)(C)COC1(C=1C=CC(Cl)=CC=1)CN1N=CN=C1 MQRHEDOAEMZEBK-UHFFFAOYSA-N 0.000 claims description 3
- LZKNVWHSYPECAV-UHFFFAOYSA-N 1-[[2-(4-chlorophenyl)-5,5-dimethyloxolan-2-yl]methyl]-1,2,4-triazole Chemical compound O1C(C)(C)CCC1(C=1C=CC(Cl)=CC=1)CN1N=CN=C1 LZKNVWHSYPECAV-UHFFFAOYSA-N 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- ZUQAPLKKNAQJAU-UHFFFAOYSA-N acetylenediol Chemical compound OC#CO ZUQAPLKKNAQJAU-UHFFFAOYSA-N 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 239000003610 charcoal Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- NMIJLVJGUKKHMU-UHFFFAOYSA-N 1-[[2-(2,4-dichlorophenyl)-4-propyloxolan-2-yl]methyl]-1,2,4-triazole Chemical compound C1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 NMIJLVJGUKKHMU-UHFFFAOYSA-N 0.000 claims description 2
- QEZZBERJSBJDKN-UHFFFAOYSA-N 1-[[2-(2,4-dichlorophenyl)-5,5-dimethyloxolan-2-yl]methyl]-1,2,4-triazole Chemical compound O1C(C)(C)CCC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 QEZZBERJSBJDKN-UHFFFAOYSA-N 0.000 claims description 2
- FFWDNOAQDVXQIO-UHFFFAOYSA-N 1-[[2-(2-chlorophenyl)-5-methyloxolan-2-yl]methyl]-1,2,4-triazole Chemical compound O1C(C)CCC1(C=1C(=CC=CC=1)Cl)CN1N=CN=C1 FFWDNOAQDVXQIO-UHFFFAOYSA-N 0.000 claims description 2
- DTGHOKVOMHMIQQ-UHFFFAOYSA-N 1-[[2-(4-chlorophenyl)-3-methyloxolan-2-yl]methyl]-1,2,4-triazole Chemical compound CC1CCOC1(C=1C=CC(Cl)=CC=1)CN1N=CN=C1 DTGHOKVOMHMIQQ-UHFFFAOYSA-N 0.000 claims description 2
- NWJJOMFEEUUYFB-UHFFFAOYSA-N 1-[[2-(4-chlorophenyl)-3-propyloxolan-2-yl]methyl]-1,2,4-triazole Chemical compound CCCC1CCOC1(C=1C=CC(Cl)=CC=1)CN1N=CN=C1 NWJJOMFEEUUYFB-UHFFFAOYSA-N 0.000 claims description 2
- HEGRBURSVOAKNK-UHFFFAOYSA-N 1-[[2-(4-chlorophenyl)-4-ethyloxolan-2-yl]methyl]-1,2,4-triazole Chemical compound C1C(CC)COC1(C=1C=CC(Cl)=CC=1)CN1N=CN=C1 HEGRBURSVOAKNK-UHFFFAOYSA-N 0.000 claims description 2
- WFPQFTPLQQZKCP-UHFFFAOYSA-N 1-[[2-(4-chlorophenyl)-4-methyloxolan-2-yl]methyl]-1,2,4-triazole Chemical compound C1C(C)COC1(C=1C=CC(Cl)=CC=1)CN1N=CN=C1 WFPQFTPLQQZKCP-UHFFFAOYSA-N 0.000 claims description 2
- MLCPPFMHOGCGGG-UHFFFAOYSA-N 1-[[2-(4-chlorophenyl)-4-propyloxolan-2-yl]methyl]-1,2,4-triazole Chemical compound C1C(CCC)COC1(C=1C=CC(Cl)=CC=1)CN1N=CN=C1 MLCPPFMHOGCGGG-UHFFFAOYSA-N 0.000 claims description 2
- KUTWKGKKHRASAR-UHFFFAOYSA-N 1-[[2-(4-methoxyphenyl)-5,5-dimethyloxolan-2-yl]methyl]-1,2,4-triazole Chemical compound C1=CC(OC)=CC=C1C1(CN2N=CN=C2)OC(C)(C)CC1 KUTWKGKKHRASAR-UHFFFAOYSA-N 0.000 claims description 2
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- DKWOHBPRFZIUQL-UHFFFAOYSA-N dimethyl-methylidene-oxo-$l^{6}-sulfane Chemical compound C[S+](C)([CH2-])=O DKWOHBPRFZIUQL-UHFFFAOYSA-N 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 238000006263 metalation reaction Methods 0.000 claims description 2
- JIQNWFBLYKVZFY-UHFFFAOYSA-N methoxycyclohexatriene Chemical compound COC1=C[C]=CC=C1 JIQNWFBLYKVZFY-UHFFFAOYSA-N 0.000 claims description 2
- 150000002905 orthoesters Chemical class 0.000 claims description 2
- 150000004965 peroxy acids Chemical class 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims 6
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 2
- 229910052763 palladium Inorganic materials 0.000 claims 2
- QLWXGJHHNBDFDK-UHFFFAOYSA-N 1-[[2-(2,4-dichlorophenyl)-5-methyloxolan-2-yl]methyl]-1,2,4-triazole Chemical compound O1C(C)CCC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 QLWXGJHHNBDFDK-UHFFFAOYSA-N 0.000 claims 1
- COWDYFUQIYRMJU-UHFFFAOYSA-N 1-[[5,5-dimethyl-2-(4-methylphenyl)oxolan-2-yl]methyl]-1,2,4-triazole Chemical compound C1=CC(C)=CC=C1C1(CN2N=CN=C2)OC(C)(C)CC1 COWDYFUQIYRMJU-UHFFFAOYSA-N 0.000 claims 1
- AXNHDFFWLBZMJT-UHFFFAOYSA-N 1-[[5,5-dimethyl-2-(4-propan-2-ylphenyl)oxolan-2-yl]methyl]-1,2,4-triazole Chemical compound C1=CC(C(C)C)=CC=C1C1(CN2N=CN=C2)OC(C)(C)CC1 AXNHDFFWLBZMJT-UHFFFAOYSA-N 0.000 claims 1
- ZSPTYLOMNJNZNG-UHFFFAOYSA-N 3-Buten-1-ol Chemical compound OCCC=C ZSPTYLOMNJNZNG-UHFFFAOYSA-N 0.000 claims 1
- 101100172879 Caenorhabditis elegans sec-5 gene Proteins 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- GZRYBYIBLHMWCD-UHFFFAOYSA-N dimethyl(methylidene)-$l^{4}-sulfane Chemical compound CS(C)=C GZRYBYIBLHMWCD-UHFFFAOYSA-N 0.000 claims 1
- 239000005648 plant growth regulator Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 79
- 239000000243 solution Substances 0.000 description 42
- 201000010099 disease Diseases 0.000 description 34
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 34
- 230000008635 plant growth Effects 0.000 description 27
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- 238000012360 testing method Methods 0.000 description 26
- 239000003921 oil Substances 0.000 description 23
- 235000019198 oils Nutrition 0.000 description 23
- 230000001105 regulatory effect Effects 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- 230000000694 effects Effects 0.000 description 20
- 230000012010 growth Effects 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 19
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
- 235000019441 ethanol Nutrition 0.000 description 18
- 230000002829 reductive effect Effects 0.000 description 17
- 240000005979 Hordeum vulgare Species 0.000 description 16
- 235000013339 cereals Nutrition 0.000 description 16
- 239000007921 spray Substances 0.000 description 16
- 239000007788 liquid Substances 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 14
- 240000007594 Oryza sativa Species 0.000 description 13
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 239000004615 ingredient Substances 0.000 description 12
- 239000002689 soil Substances 0.000 description 12
- 235000007340 Hordeum vulgare Nutrition 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 244000025254 Cannabis sativa Species 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
- 241000209140 Triticum Species 0.000 description 10
- 239000012141 concentrate Substances 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 10
- 239000012312 sodium hydride Substances 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 235000007164 Oryza sativa Nutrition 0.000 description 9
- 235000021307 Triticum Nutrition 0.000 description 9
- 239000003337 fertilizer Substances 0.000 description 9
- 150000002924 oxiranes Chemical class 0.000 description 9
- 235000009566 rice Nutrition 0.000 description 9
- 241000221785 Erysiphales Species 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 241000220225 Malus Species 0.000 description 7
- 241000219094 Vitaceae Species 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 235000021021 grapes Nutrition 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 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 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000002361 compost Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 235000013399 edible fruits Nutrition 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
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- 239000002917 insecticide Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
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- 150000002500 ions Chemical class 0.000 description 1
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
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- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- QANMHLXAZMSUEX-UHFFFAOYSA-N kinetin Chemical compound N=1C=NC=2N=CNC=2C=1NCC1=CC=CO1 QANMHLXAZMSUEX-UHFFFAOYSA-N 0.000 description 1
- 229960001669 kinetin Drugs 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
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- 235000021374 legumes Nutrition 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940100892 mercury compound Drugs 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 1
- CNTVWMRWECWTRT-UHFFFAOYSA-N methyl 2,5-dichloro-4-methoxybenzoate Chemical compound COC(=O)C1=CC(Cl)=C(OC)C=C1Cl CNTVWMRWECWTRT-UHFFFAOYSA-N 0.000 description 1
- SLONBSAYACJVRR-UHFFFAOYSA-N methyl 4-(4-chlorophenyl)-4-oxobutanoate Chemical compound COC(=O)CCC(=O)C1=CC=C(Cl)C=C1 SLONBSAYACJVRR-UHFFFAOYSA-N 0.000 description 1
- JNAUYPUFUALLEH-UHFFFAOYSA-N methyl 4-(4-chlorophenyl)pent-4-enoate Chemical compound COC(=O)CCC(=C)C1=CC=C(Cl)C=C1 JNAUYPUFUALLEH-UHFFFAOYSA-N 0.000 description 1
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
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- XQIJIALOJPIKGX-UHFFFAOYSA-N naphthalene 1,2-oxide Chemical compound C1=CC=C2C3OC3C=CC2=C1 XQIJIALOJPIKGX-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical compound NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
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- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- 230000005080 plant death Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
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- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000013138 pruning Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012882 rooting medium Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 238000004162 soil erosion Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- SSTZGACKDAVIGZ-UHFFFAOYSA-N sulfanium;bromide Chemical compound [SH3+].[Br-] SSTZGACKDAVIGZ-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 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
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood 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
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8203707 | 1982-02-09 | ||
GB8203707 | 1982-02-09 | ||
GB8211290 | 1982-04-19 | ||
GB8213652 | 1982-05-11 | ||
GB8231263 | 1982-11-02 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS58148880A JPS58148880A (ja) | 1983-09-05 |
JPH0526789B2 true JPH0526789B2 (de) | 1993-04-19 |
Family
ID=10528204
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1899283A Granted JPS58148880A (ja) | 1982-02-09 | 1983-02-09 | トリアゾ−ル又はイミダゾ−ル化合物、それらの製造法及びそれらを活性成分とする殺カビ又は植物生長調節剤 |
Country Status (2)
Country | Link |
---|---|
JP (1) | JPS58148880A (de) |
ZA (1) | ZA83308B (de) |
-
1983
- 1983-01-17 ZA ZA83308A patent/ZA83308B/xx unknown
- 1983-02-09 JP JP1899283A patent/JPS58148880A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
ZA83308B (en) | 1983-10-26 |
JPS58148880A (ja) | 1983-09-05 |
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