JPH0242801B2 - - Google Patents
Info
- Publication number
- JPH0242801B2 JPH0242801B2 JP55182407A JP18240780A JPH0242801B2 JP H0242801 B2 JPH0242801 B2 JP H0242801B2 JP 55182407 A JP55182407 A JP 55182407A JP 18240780 A JP18240780 A JP 18240780A JP H0242801 B2 JPH0242801 B2 JP H0242801B2
- Authority
- JP
- Japan
- Prior art keywords
- dimethyl
- triazol
- penten
- acid
- compound
- 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
- -1 triazolyl alcohol derivative Chemical class 0.000 claims description 73
- 230000003287 optical effect Effects 0.000 claims description 8
- 239000005648 plant growth regulator Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
- 239000000243 solution Substances 0.000 description 40
- 150000001875 compounds Chemical class 0.000 description 37
- 239000000203 mixture Substances 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
- 230000002829 reductive effect Effects 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000004009 herbicide Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 229910010082 LiAlH Inorganic materials 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 239000010446 mirabilite Substances 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 150000003852 triazoles Chemical group 0.000 description 8
- YNWVFADWVLCOPU-MDWZMJQESA-N (1E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1/C(C(O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MDWZMJQESA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 230000012010 growth Effects 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 239000012046 mixed solvent Substances 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 6
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 239000003638 chemical reducing agent Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- FBOUIAKEJMZPQG-AWNIVKPZSA-N (1E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1/C(C(O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-AWNIVKPZSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 5
- 239000000417 fungicide Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 230000008635 plant growth Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- LFLAXRVXFCJYOI-AWNIVKPZSA-N (e)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1/C(C(=O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl LFLAXRVXFCJYOI-AWNIVKPZSA-N 0.000 description 4
- 241000723353 Chrysanthemum Species 0.000 description 4
- 235000007516 Chrysanthemum Nutrition 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 150000001336 alkenes Chemical group 0.000 description 4
- 150000001414 amino alcohols Chemical class 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- DTGKSKDOIYIVQL-QXFUBDJGSA-N (-)-borneol Chemical compound C1C[C@]2(C)[C@H](O)C[C@H]1C2(C)C DTGKSKDOIYIVQL-QXFUBDJGSA-N 0.000 description 3
- 229930006703 (-)-borneol Natural products 0.000 description 3
- LACMLEGEQFCFAZ-MDWZMJQESA-N (e)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1/C(C(=O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 LACMLEGEQFCFAZ-MDWZMJQESA-N 0.000 description 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 3
- 244000141359 Malus pumila Species 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ZKWVEWDWYSIYKA-FSJBWODESA-N [5-[(E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-yl]-5-methyl-2-propan-2-ylcyclohexyl] ethaneperoxoate Chemical compound C(C)(=O)OOC1CC(CCC1C(C)C)(C)C(\C(=C/C1=C(C=C(C=C1)Cl)Cl)\N1N=CN=C1)C(C)(C)C ZKWVEWDWYSIYKA-FSJBWODESA-N 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- 230000009036 growth inhibition Effects 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- GTVRLHPVICIJFQ-UHFFFAOYSA-N hexane;tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl.CCCCCC GTVRLHPVICIJFQ-UHFFFAOYSA-N 0.000 description 3
- 229960004873 levomenthol Drugs 0.000 description 3
- MAGPZHKLEZXLNU-UHFFFAOYSA-N mandelamide Chemical compound NC(=O)C(O)C1=CC=CC=C1 MAGPZHKLEZXLNU-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- VIUQEVFZJAFLTR-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl) ethaneperoxoate Chemical compound CC(C)C1CCC(C)CC1OOC(C)=O VIUQEVFZJAFLTR-UHFFFAOYSA-N 0.000 description 2
- IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 description 2
- VNMCKLVHDJADEB-OUAUKWLOSA-N 2-[(1r,2s,5r)-5-methyl-2-propan-2-ylcyclohexyl]oxyacetyl chloride Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OCC(Cl)=O VNMCKLVHDJADEB-OUAUKWLOSA-N 0.000 description 2
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- IFWRTGJDSLZNQE-OEAKJJBVSA-N C(C)(=O)OOC1CC(CCC1C(C)C)(C)C(\C(=C/C1=CC=C(C=C1)Cl)\N1N=CN=C1)C(C)(C)C Chemical compound C(C)(=O)OOC1CC(CCC1C(C)C)(C)C(\C(=C/C1=CC=C(C=C1)Cl)\N1N=CN=C1)C(C)(C)C IFWRTGJDSLZNQE-OEAKJJBVSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- 241000208422 Rhododendron Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- SAXHIDRUJXPDOD-UHFFFAOYSA-N ethyl hydroxy(phenyl)acetate Chemical compound CCOC(=O)C(O)C1=CC=CC=C1 SAXHIDRUJXPDOD-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 2
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- FMCGSUUBYTWNDP-ONGXEEELSA-N (1R,2S)-2-(dimethylamino)-1-phenyl-1-propanol Chemical compound CN(C)[C@@H](C)[C@H](O)C1=CC=CC=C1 FMCGSUUBYTWNDP-ONGXEEELSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 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
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- LWHIYPYQKDPFBK-UHFFFAOYSA-L zinc;n,n-dimethylcarbamothioate Chemical compound [Zn+2].CN(C)C([O-])=S.CN(C)C([O-])=S LWHIYPYQKDPFBK-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (31)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18240780A JPS57106669A (en) | 1980-12-22 | 1980-12-22 | Optically active triazolyl alcohol derivative, its preparation, and plant growth regulator and herbicide containing said derivative as active component |
| AU77925/81A AU544099B2 (en) | 1980-12-15 | 1981-11-26 | Triazolylpentenols |
| CA000391391A CA1172641A (en) | 1980-12-15 | 1981-12-02 | Optical isomer of triazolylpentenols, and their production and use as fungicide, herbicide and/or plant growth regulant |
| NZ199185A NZ199185A (en) | 1980-12-15 | 1981-12-07 | Optical isomers of cis and trans geometric isomers of 1-(44-chloro or 2,4-dichloro)phenyl)-2(1,2,4-triazol-1-yl)-4,4-dimethylpent-1-en-3-ols |
| US06/328,191 US4435203A (en) | 1980-12-15 | 1981-12-07 | Optical isomer of triazolylpentenols, and their production and use as fungicide, herbicide and/or plant growth regulant |
| IL64481A IL64481A0 (en) | 1980-12-15 | 1981-12-08 | Optical isomers of triazolylpentenols,methods for their production and fungicidal,herbicidal and/or plant growth regulant compositions containing them |
| EG71881A EG15461A (en) | 1980-12-22 | 1981-12-08 | Optical isomer of triazolylpentnols,and their production and use as fungicides,herbicide and plant growth regulant |
| RO105975A RO84279B (ro) | 1980-12-15 | 1981-12-11 | Procedeu de preparare a unor derivati de triazolil-alcool optic activi |
| ES507883A ES507883A0 (es) | 1980-12-15 | 1981-12-11 | Un procedimiento para preparar derivados de alcohol triazolilico . |
| RO110153A RO86318B (ro) | 1980-12-15 | 1981-12-11 | Compozitie solida fungicida, erbicida si de reglare a cresterii plantelor |
| RO81116061A RO89367A (ro) | 1980-12-15 | 1981-12-11 | Compozitie lichida erbicida,fungicida si de reglare a cresterii plantelor |
| EP85111505A EP0175278A3 (en) | 1980-12-15 | 1981-12-14 | Optical isomer of triazolylpentenols, and their production and use as fungicide herbicide and/or plant growth regulant |
| YU2922/81A YU43055B (en) | 1980-12-15 | 1981-12-14 | Process for producing triazolyl alcohol derivatives |
| DE8484200456T DE3177274D1 (de) | 1980-12-15 | 1981-12-14 | (+)-triazolylpentenolderivat, seine herstellung und verwendung als herbizid und/oder pflanzenwachstumsregulator. |
| EP90121117A EP0427168B1 (en) | 1980-12-15 | 1981-12-14 | Optical isomer of triazolylpentenols, and their production and use as fungicide, herbicide and/or plant growth regulant |
| SI8112922A SI8112922A8 (sl) | 1980-12-15 | 1981-12-14 | Postopek za proizvodnjo derivatov triazolil alkohola |
| EP19840200456 EP0121284B1 (en) | 1980-12-15 | 1981-12-14 | (+)-triazolylpentenol derivative, its production and use as herbicide and/or plant growth regulant |
| DE3177314T DE3177314T2 (de) | 1980-12-15 | 1981-12-14 | Optisch isomeres Triazolylpentenol. Verfahren zur Herstellung und Verwendung als Fungizid, Herbizid und/oder Wachstumsregulator |
| HU813755A HU187385B (en) | 1980-12-15 | 1981-12-14 | Fungicides, herbicides and plant growth regulating compositions, as well as process for the preparation of optically active triazolyl-alcohol derivatives which can be used as active ingredients of sid compositions |
| EP81305873A EP0054431B1 (en) | 1980-12-15 | 1981-12-14 | Optical isomer of a triazolylpentenol, and its production and use as fungicide |
| DK553881A DK160301C (da) | 1980-12-15 | 1981-12-14 | (-)-(e)-triazolylpentenoler, fungicider deraf og fremgangsmaade til bekaempelse af svampe |
| SU813366002A SU1582987A3 (ru) | 1980-12-15 | 1981-12-14 | Способ получени (+) или (-) производных триазолилового спирта |
| BR8108116A BR8108116A (pt) | 1980-12-15 | 1981-12-14 | Derivado de alcool triazolilico,processo para produzir o mesmo,composicao fungicida,composicao herbicida e reguladora do crescimento de plantas e processo para matar um fungo,processo para controlar o crescimento de plantas e processo para matar ervas daninhas |
| DE8181305873T DE3175949D1 (en) | 1980-12-15 | 1981-12-14 | Optical isomer of a triazolylpentenol, and its production and use as fungicide |
| KR1019810004924A KR870001792B1 (ko) | 1980-12-15 | 1981-12-15 | 트리아졸일펜테놀류의 광학 이성체의 제조 방법 |
| MYPI87002389A MY102222A (en) | 1980-12-15 | 1987-09-30 | Optical isomer of triazolylpentenols, and their production and use as fungicide, herbicide and/or plant growth regulant. |
| MYPI87002423A MY102225A (en) | 1980-12-15 | 1987-09-30 | Optical isomer of triazolylpentenols, and their production and use as fungicide, herbicide and/or plant regulant. |
| SU4613542 RU2017423C1 (ru) | 1980-12-22 | 1989-03-01 | Рострегулирующая композиция |
| DK102190A DK162223C (da) | 1980-12-15 | 1990-04-25 | (+)-(e)-triazolylpentenoler samt herbicide og/eller plantevaekstregulerende midler deraf og fremgangsmaader til regulering af plantevaekst og til udryddelse af ukrudt |
| SU5011447 RU2051911C1 (ru) | 1980-12-22 | 1992-04-10 | (+)-оптически активное производное триазолилового спирта |
| HRP-2922/81A HRP931272B1 (en) | 1980-12-15 | 1993-10-06 | Process for the preparation of triazolyl alchocole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18240780A JPS57106669A (en) | 1980-12-22 | 1980-12-22 | Optically active triazolyl alcohol derivative, its preparation, and plant growth regulator and herbicide containing said derivative as active component |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63285303A Division JPH0613533B2 (ja) | 1988-11-10 | 1988-11-10 | 水素化アルミニウムリチウム系不斉還元剤 |
| JP11262290A Division JPH02288809A (ja) | 1990-04-26 | 1990-04-26 | 光学活性トリアゾリルアルコール誘導体を有効成分として含有する除草剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57106669A JPS57106669A (en) | 1982-07-02 |
| JPH0242801B2 true JPH0242801B2 (zh) | 1990-09-26 |
Family
ID=16117754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18240780A Granted JPS57106669A (en) | 1980-12-15 | 1980-12-22 | Optically active triazolyl alcohol derivative, its preparation, and plant growth regulator and herbicide containing said derivative as active component |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS57106669A (zh) |
| EG (1) | EG15461A (zh) |
| RU (2) | RU2017423C1 (zh) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59184168A (ja) * | 1983-04-04 | 1984-10-19 | Sumitomo Chem Co Ltd | 光学活性アルコ−ル誘導体の製造法 |
| JPS60174772A (ja) * | 1984-02-20 | 1985-09-09 | Sumitomo Chem Co Ltd | 光学活性アルコ−ル誘導体の製造法 |
| JPS59166527U (ja) * | 1983-04-20 | 1984-11-08 | 松下電器産業株式会社 | Ｓｓｂ送信機 |
| EP0178325B1 (en) * | 1984-04-03 | 1992-04-22 | Sumitomo Chemical Company, Limited | Boron hydride type compounds and their use in a method for producing optically active alpha,beta unsaturated alcohols |
| JPS6118790A (ja) * | 1984-07-05 | 1986-01-27 | Sumitomo Chem Co Ltd | 光学活性ボラン錯体およびその製造法 |
| DE3440112A1 (de) * | 1984-11-02 | 1986-05-07 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung optisch aktiver azolylcarbinol-derivate |
| US5698742A (en) * | 1984-11-21 | 1997-12-16 | Sumitomo Chemical Company, Limited | Method for producing an optically active azolyl-α, β-unsaturated alcohol |
| JPH0613533B2 (ja) * | 1988-11-10 | 1994-02-23 | 住友化学工業株式会社 | 水素化アルミニウムリチウム系不斉還元剤 |
| JP5266247B2 (ja) * | 2006-12-07 | 2013-08-21 | ビーエーエスエフ ソシエタス・ヨーロピア | 殺菌性トリアゾールおよびアルコキシル化アルコールを含む組成物およびキットならびにそれらの使用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5441875A (en) * | 1977-09-07 | 1979-04-03 | Sumitomo Chem Co Ltd | Azole homolog, its preparation and bactericidal agent containing the same |
| JPS55124771A (en) * | 1979-03-20 | 1980-09-26 | Sumitomo Chem Co Ltd | Triazole-based geometrical isomerism compound or its salt, its preparation, and fungicide for agriculture and gardening comprising it as active ingredient |
-
1980
- 1980-12-22 JP JP18240780A patent/JPS57106669A/ja active Granted
-
1981
- 1981-12-08 EG EG71881A patent/EG15461A/xx active
-
1989
- 1989-03-01 RU SU4613542 patent/RU2017423C1/ru active
-
1992
- 1992-04-10 RU SU5011447 patent/RU2051911C1/ru active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5441875A (en) * | 1977-09-07 | 1979-04-03 | Sumitomo Chem Co Ltd | Azole homolog, its preparation and bactericidal agent containing the same |
| JPS55124771A (en) * | 1979-03-20 | 1980-09-26 | Sumitomo Chem Co Ltd | Triazole-based geometrical isomerism compound or its salt, its preparation, and fungicide for agriculture and gardening comprising it as active ingredient |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2017423C1 (ru) | 1994-08-15 |
| RU2051911C1 (ru) | 1996-01-10 |
| EG15461A (en) | 1987-05-30 |
| JPS57106669A (en) | 1982-07-02 |
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