JPH0115509B2 - - Google Patents
Info
- Publication number
- JPH0115509B2 JPH0115509B2 JP11657679A JP11657679A JPH0115509B2 JP H0115509 B2 JPH0115509 B2 JP H0115509B2 JP 11657679 A JP11657679 A JP 11657679A JP 11657679 A JP11657679 A JP 11657679A JP H0115509 B2 JPH0115509 B2 JP H0115509B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- isomer
- formula
- present
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 triazole compound Chemical class 0.000 claims description 33
- 239000004009 herbicide Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 10
- 230000000855 fungicidal effect Effects 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 239000000417 fungicide Substances 0.000 claims description 7
- 230000002363 herbicidal effect Effects 0.000 claims description 7
- 239000005648 plant growth regulator Substances 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 60
- 241000196324 Embryophyta Species 0.000 description 19
- 201000010099 disease Diseases 0.000 description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 18
- 241000221785 Erysiphales Species 0.000 description 17
- 239000000203 mixture Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 240000007594 Oryza sativa Species 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 235000007164 Oryza sativa Nutrition 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 235000009566 rice Nutrition 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- 240000005979 Hordeum vulgare Species 0.000 description 7
- 235000007340 Hordeum vulgare Nutrition 0.000 description 7
- 241000209140 Triticum Species 0.000 description 7
- 235000021307 Triticum Nutrition 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
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- 239000002585 base Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
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- 150000003852 triazoles Chemical group 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
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- 241001076438 Oxya japonica Species 0.000 description 4
- 206010039509 Scab Diseases 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000001580 bacterial effect Effects 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 206010027146 Melanoderma Diseases 0.000 description 3
- 244000184734 Pyrus japonica Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001336 alkenes Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052987 metal hydride Inorganic materials 0.000 description 3
- 150000004681 metal hydrides Chemical class 0.000 description 3
- 244000000003 plant pathogen Species 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 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
- NOWIFXJVIXPVEL-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-(1-methylcyclopropyl)-2-(1,2,4-triazol-1-yl)prop-2-en-1-one Chemical compound C=1C=C(Cl)C=CC=1C=C(N1N=CN=C1)C(=O)C1(C)CC1 NOWIFXJVIXPVEL-UHFFFAOYSA-N 0.000 description 2
- 235000016068 Berberis vulgaris Nutrition 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000007516 Chrysanthemum Nutrition 0.000 description 2
- 240000005250 Chrysanthemum indicum Species 0.000 description 2
- 241000234653 Cyperus Species 0.000 description 2
- 241000237858 Gastropoda Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 239000005574 MCPA Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 244000234609 Portulaca oleracea Species 0.000 description 2
- 235000001855 Portulaca oleracea Nutrition 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Natural products O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000000645 desinfectant Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000887 hydrating effect Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 239000007858 starting material Substances 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
- 239000005720 sucrose Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229940035893 uracil Drugs 0.000 description 2
- 239000000080 wetting agent Substances 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
- 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
- LIVCNGIOYZNYHR-UHFFFAOYSA-N 1-[amino(hydroxy)phosphinothioyl]oxybutane Chemical group CCCCOP(N)(O)=S LIVCNGIOYZNYHR-UHFFFAOYSA-N 0.000 description 1
- YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
- USNFYCRVHZFXRC-UHFFFAOYSA-N 2-[3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropyl]-2-(3-phenoxyphenyl)acetonitrile Chemical compound CC1(C)C(C=C(Br)Br)C1C(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 USNFYCRVHZFXRC-UHFFFAOYSA-N 0.000 description 1
- QRNATDQRFAUDKF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate Chemical compound NC(=S)SCCSC(N)=S QRNATDQRFAUDKF-UHFFFAOYSA-N 0.000 description 1
- JMZRZEXRYJUHEB-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;zinc Chemical compound [Zn].NC(=S)SCCSC(N)=S JMZRZEXRYJUHEB-UHFFFAOYSA-N 0.000 description 1
- LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 1
- ITUJTNVTYSHLGM-UHFFFAOYSA-N 2-methylsulfanyl-4,6-di(propan-2-yl)-2h-1,3,5-triazin-1-amine Chemical compound CSC1N=C(C(C)C)N=C(C(C)C)N1N ITUJTNVTYSHLGM-UHFFFAOYSA-N 0.000 description 1
- TVHCLUNXRJSPGX-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-1,1-dimethylurea;3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1.CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 TVHCLUNXRJSPGX-UHFFFAOYSA-N 0.000 description 1
- QYXNPZDJNXKGJS-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-(1-methylcyclopropyl)-2-(1,2,4-triazol-1-yl)prop-2-en-1-ol Chemical compound C=1C=C(Cl)C=CC=1C=C(N1N=CN=C1)C(O)C1(C)CC1 QYXNPZDJNXKGJS-UHFFFAOYSA-N 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
- NXQLJXDDTJJCKW-UHFFFAOYSA-N 3-methyl-6-phenyl-3h-1,2,4-triazin-4-amine Chemical compound NN1C(C)N=NC(C=2C=CC=CC=2)=C1 NXQLJXDDTJJCKW-UHFFFAOYSA-N 0.000 description 1
- CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 description 1
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- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 description 1
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- 239000000969 carrier Substances 0.000 description 1
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- XQNAUQUKWRBODG-UHFFFAOYSA-N chlornitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=C(Cl)C=C(Cl)C=C1Cl XQNAUQUKWRBODG-UHFFFAOYSA-N 0.000 description 1
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
- 244000118869 coast club rush Species 0.000 description 1
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
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- 230000003247 decreasing effect Effects 0.000 description 1
- XRBGEQKKQIRUOE-UHFFFAOYSA-N dialuminum ethyl phosphite Chemical compound [Al+3].[Al+3].CCOP([O-])[O-].CCOP([O-])[O-].CCOP([O-])[O-] XRBGEQKKQIRUOE-UHFFFAOYSA-N 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
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- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
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- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 1
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- 238000004817 gas chromatography Methods 0.000 description 1
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- OXHDYFKENBXUEM-UHFFFAOYSA-N glyphosine Chemical compound OC(=O)CN(CP(O)(O)=O)CP(O)(O)=O OXHDYFKENBXUEM-UHFFFAOYSA-N 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 230000009422 growth inhibiting effect Effects 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- AGZFDMRWOVHNRR-UHFFFAOYSA-N methyl n-(1h-benzimidazol-2-yl)-n-(butylcarbamoyl)carbamate Chemical compound C1=CC=C2NC(N(C(=O)OC)C(=O)NCCCC)=NC2=C1 AGZFDMRWOVHNRR-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000013459 phenoxy herbicide Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000007699 photoisomerization reaction Methods 0.000 description 1
- YEBIHIICWDDQOL-YBHNRIQQSA-N polyoxin Polymers O[C@@H]1[C@H](O)[C@@H](C(C=O)N)O[C@H]1N1C(=O)NC(=O)C(C(O)=O)=C1 YEBIHIICWDDQOL-YBHNRIQQSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- QXJKBPAVAHBARF-UHFFFAOYSA-N procymidone Chemical compound O=C1C2(C)CC2(C)C(=O)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-UHFFFAOYSA-N 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 235000012046 side dish Nutrition 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 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
- 201000008827 tuberculosis Diseases 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 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 (25)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11657679A JPS5640671A (en) | 1979-09-10 | 1979-09-10 | Triazole compound or its salt, its preparation and agricultural and horticultural germicide, herbicide and plant growth regulator containing the same as active constituent |
| US06/130,108 US4554007A (en) | 1979-03-20 | 1980-03-13 | Geometrical isomer of 1-substituted-1-triazolylstyrenes, and their production and use as fungicide, herbicide and/or plant growth regulant |
| ES489674A ES8103739A1 (es) | 1979-03-20 | 1980-03-18 | Un procedimiento para preparar 1-triazolilestirenos susti- tuidos en posicion 1 |
| IT48189/80A IT1143014B (it) | 1979-03-20 | 1980-03-18 | Isomeri geometrici di 1-sostituiti-1-triazolistireni aventi attivita' fungicida diserbante e regolatrice della crescita delle piante e procedimento per la loro preparazione |
| BR8001617A BR8001617A (pt) | 1979-03-20 | 1980-03-18 | Isomero geometrico de 1-substuido-1-triazolil estirenos, e sua producao e uso como fungicida, herbicida e/ou regulador do crescimento da planta |
| SU802895951A RU2039049C1 (ru) | 1979-03-20 | 1980-03-18 | Производные 1-фенил-2-(1,2,4-триазол-1-ил) пропена e-изомера и фунгицидная композиция на их основе |
| CA000347897A CA1154449A (en) | 1979-03-20 | 1980-03-18 | Geometrical isomer of 1-substituted-1- triazolylstyrenes, and their production and use as fungicide, herbicide and/or plant growth regulant |
| NZ193168A NZ193168A (en) | 1979-03-20 | 1980-03-18 | Certain geometric isomers of 1-phenyl-2-(1,2,4-triazol-1-yl)-3-hydrocarbylpropan-3-ols |
| HU80652A HU186281B (en) | 1979-03-20 | 1980-03-19 | Fungicide, herbicide and control preparation of plant growing and process for producing 1-subsituted-1-triazoly-styrene derivatives used for same |
| YU766/80A YU42969B (en) | 1979-03-20 | 1980-03-19 | Process for producing geometric isomers of 1-substituted-1-triazolyl styroles |
| DE19803010560 DE3010560A1 (de) | 1979-03-20 | 1980-03-19 | Geometrische isomere von triazolverbindungen und diese enthaltende fungizide, herbizide und/oder das pflanzenwachstum steuernde mittel |
| CH217080A CH644851A5 (de) | 1979-03-20 | 1980-03-19 | Geometrische e-isomere von in 1-stellung substituierten 1-triazolylstyrolen. |
| AR280359A AR226305A1 (es) | 1979-03-20 | 1980-03-19 | Isomero geometrico del-fenil-2-triazol(1,2,4)-propen-3-ol util como herbicida y regulador del crecimiento vegetal |
| DK118580A DK157811C (da) | 1979-03-20 | 1980-03-19 | Geometriske isomere af 1-substituerede-1-triazolylstyrener, mellemprodukt til brug ved deres fremstilling og fungicid, herbicid og/eller plantevaekstregulator indeholdende de geometriske isomere |
| CS801903A CS241472B2 (cs) | 1979-03-20 | 1980-03-19 | Fungicidní prostředek, herbicidní prostředek a/nebo prostředek ovlivňující růst rostlin |
| AU56571/80A AU536825B2 (en) | 1979-03-20 | 1980-03-19 | Geometrical isomer of 1-substituted-1-triazolyl-styrenes |
| GB8009190A GB2046260B (en) | 1979-03-20 | 1980-03-19 | Geometrical isomer of 1-substituted-1-triazolylstyrenes and their production and use as fungicides herbicides and/or plant growth regulations |
| FR8006155A FR2460939B1 (fr) | 1979-03-20 | 1980-03-19 | Isomeres geometriques de 1-triazolylstyrenes 1-substitues, leurs intermediaires de synthese, leur production et leur utilisation en agriculture et horticulture |
| IL59671A IL59671A (en) | 1979-03-20 | 1980-03-19 | Geometrical isomers of 1-substituted-1-triazolylstyrenes and their production and use as herbicides and/or plant growth regulants |
| PL1980222822A PL123010B1 (en) | 1979-03-20 | 1980-03-19 | Fungicidal, herbicidal and/or plant growth regulating agent and method of manufacture of novel derivatives of triazole |
| NL8001658A NL192791C (nl) | 1979-03-20 | 1980-03-20 | In hoofdzaak zuiver geometrisch isomeer van op de 1-plaats gesubstitueerde 1-triazolystyrenen, werkwijzen ter bereiding ervan, alsmede de toepassing als fungicide, herbicide en/of plantengroei-regelingsmiddel. |
| US06/772,429 US4749716A (en) | 1979-03-20 | 1985-09-04 | Geometrical isomer of 1-substituted-1-triazolystyrenes |
| MY898/87A MY8700898A (en) | 1979-03-20 | 1987-12-30 | Geometrical isomer of 1-substituted-1-triazolystyrenes, and their production and use as fungicides herbicides and/or plant growth regulants |
| SU4895674 RU2043026C1 (ru) | 1979-08-06 | 1991-06-24 | Композиция для замедления роста культурных растений |
| LVP-92-391A LV10023B (en) | 1979-03-20 | 1992-12-22 | Geometrical isomer of 1-substituted-1-triazolylstyrenes, and their production and use as fungicide, herbicide and/or plant growth regulant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11657679A JPS5640671A (en) | 1979-09-10 | 1979-09-10 | Triazole compound or its salt, its preparation and agricultural and horticultural germicide, herbicide and plant growth regulator containing the same as active constituent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5640671A JPS5640671A (en) | 1981-04-16 |
| JPH0115509B2 true JPH0115509B2 (zh) | 1989-03-17 |
Family
ID=14690527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11657679A Granted JPS5640671A (en) | 1979-03-20 | 1979-09-10 | Triazole compound or its salt, its preparation and agricultural and horticultural germicide, herbicide and plant growth regulator containing the same as active constituent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5640671A (zh) |
-
1979
- 1979-09-10 JP JP11657679A patent/JPS5640671A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5640671A (en) | 1981-04-16 |
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