JPH0135819B2 - - Google Patents
Info
- Publication number
- JPH0135819B2 JPH0135819B2 JP55162862A JP16286280A JPH0135819B2 JP H0135819 B2 JPH0135819 B2 JP H0135819B2 JP 55162862 A JP55162862 A JP 55162862A JP 16286280 A JP16286280 A JP 16286280A JP H0135819 B2 JPH0135819 B2 JP H0135819B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- compound
- formula
- substituted benzyl
- represented
- 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 benzyl ester Chemical class 0.000 claims description 46
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 239000002917 insecticide Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 description 39
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 238000009472 formulation Methods 0.000 description 14
- 241000238631 Hexapoda Species 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 235000019445 benzyl alcohol Nutrition 0.000 description 11
- 230000000749 insecticidal effect Effects 0.000 description 10
- 241000209094 Oryza Species 0.000 description 9
- 235000007164 Oryza sativa Nutrition 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 235000009566 rice Nutrition 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 241000723353 Chrysanthemum Species 0.000 description 7
- 235000007516 Chrysanthemum Nutrition 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 241001414720 Cicadellidae Species 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-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
- 241000607479 Yersinia pestis Species 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 4
- 229960000490 permethrin Drugs 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000009331 sowing Methods 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 241000255925 Diptera Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000005228 aryl sulfonate group Chemical group 0.000 description 3
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- ZQDDFKMLOJICSL-UHFFFAOYSA-N 2,2-dichloroethenyl cyclopropanecarboxylate Chemical compound ClC(Cl)=COC(=O)C1CC1 ZQDDFKMLOJICSL-UHFFFAOYSA-N 0.000 description 2
- BWPYAVCZZUTOBY-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutanoyl chloride Chemical compound CC(C)C(C(Cl)=O)C1=CC=C(Cl)C=C1 BWPYAVCZZUTOBY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- 241000256248 Spodoptera Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000002316 fumigant Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000010998 test method Methods 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
- JIIXEQFJRLRHSW-UJURSFKZSA-N (1S,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1([C@H]([C@@H]1C=C(Br)Br)C(=O)Cl)C JIIXEQFJRLRHSW-UJURSFKZSA-N 0.000 description 1
- PTWUJNIBSWMQFA-ZZKAVYKESA-N (1S,3S)-3-(1,2-dibromo-2,2-dichloroethyl)-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1([C@H]([C@@H]1C(C(Cl)(Cl)Br)Br)C(=O)Cl)C PTWUJNIBSWMQFA-ZZKAVYKESA-N 0.000 description 1
- CHLAOFANYRDCPD-UJURSFKZSA-N (1s,3r)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@@H]1C(Cl)=O CHLAOFANYRDCPD-UJURSFKZSA-N 0.000 description 1
- MQRCYPSLRFLLOE-UHFFFAOYSA-N (4-cyanophenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=C(C#N)C=C1 MQRCYPSLRFLLOE-UHFFFAOYSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- QRNJKLBLOJXIFS-UHFFFAOYSA-N 1-(2-methylprop-1-enyl)cyclopropane-1-carbonyl chloride Chemical compound CC(=CC1(CC1)C(=O)Cl)C QRNJKLBLOJXIFS-UHFFFAOYSA-N 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical class O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- VNTCVNLNEOVBEE-UHFFFAOYSA-N 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carbonyl chloride Chemical compound CC(C)=CC1C(C(Cl)=O)C1(C)C VNTCVNLNEOVBEE-UHFFFAOYSA-N 0.000 description 1
- ABFPKTQEQNICFT-UHFFFAOYSA-M 2-chloro-1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1Cl ABFPKTQEQNICFT-UHFFFAOYSA-M 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000238662 Blatta orientalis Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001465977 Coccoidea Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- 241001466042 Fulgoromorpha Species 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000721696 Lymantria Species 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- 241001556089 Nilaparvata lugens Species 0.000 description 1
- 241000256259 Noctuidae Species 0.000 description 1
- 241000320508 Pentatomidae Species 0.000 description 1
- 241000238675 Periplaneta americana Species 0.000 description 1
- 241001325166 Phacelia congesta Species 0.000 description 1
- 241000500441 Plutellidae Species 0.000 description 1
- 241000545593 Scolytinae Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241000256251 Spodoptera frugiperda Species 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 244000037666 field crops Species 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- ITNVWQNWHXEMNS-UHFFFAOYSA-N methanolate;titanium(4+) Chemical compound [Ti+4].[O-]C.[O-]C.[O-]C.[O-]C ITNVWQNWHXEMNS-UHFFFAOYSA-N 0.000 description 1
- SFDZETWZUCDYMD-UHFFFAOYSA-N monosodium acetylide Chemical compound [Na+].[C-]#C SFDZETWZUCDYMD-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
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The present invention is based on the general formula () The present invention relates to a novel substituted benzyl ester represented by: and an insecticide containing the same as an active ingredient. However, in the above general formula (), R is the following general formula () or general formula ()
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ã«ãããŠR1ã¯[Formula] Represents a group represented by the following. In the group represented by general formula (), R 1 is
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åŠç°æ§äœãå«ãã[Formula] represents a group. Here, X and X' are the same or different and each represents a halogen atom such as a fluorine atom, chlorine atom, or bromine atom; Y and Y' are the same or different and each represents a halogen atom such as a fluorine atom, a chlorine atom, or a bromine atom; It represents a halogen atom or a methyl group; Z represents a hydrogen atom or a halogen atom such as a chlorine atom or a bromine atom. In addition, in the group represented by the general formula (), Q is a fluorine atom, a chlorine atom,
Represents a halogen atom such as a bromine atom. From the viewpoint of insecticidal activity exhibited by the substituted benzyl ester represented by the general formula (), the nitro group of the substituent is preferably located at the meta or para position, and the group represented by the general formula () or the general formula () Among these, groups represented by the following general formula ()' are particularly preferred. [In the formula, X has the same meaning as in the general formula (). ] Conventionally, 4-cyanobenzyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate, 4-trifluoromethylbenzyl 2,2-dimethyl-3-(2-methyl-1- Chrysanthemum carboxylic acid benzyl esters such as propenyl) cyclopropanecarboxylate, 2,6-dichloro-4-nitrobenzyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate have insecticidal activity. However, the insecticidal activity of these chrysanthemum carboxylic acid benzyl esters is not satisfactory, and their residual efficacy is low. Also 4-nitrobenzyl (10)
-trans-2,2-dimethyl-3-(2,2-
It has been reported that the American cockroach hydrolytically metabolizes substituted benzyl chrysanthemum esters such as (dichlorvinyl) cyclopropane carboxylate (see Abstracts of the 5th Annual Conference of the Japanese Society of Pesticides, No. 115); however, these substituted benzyl chrysanthemum esters has low insecticidal activity. The present inventors have conducted intensive research to create an excellent pyrethroid compound with higher insecticidal activity than these conventional chrysanthemum acid esters, and as a result, the general formula ()
The substituted benzyl ester shown in (1) has significantly higher and faster insecticidal efficacy than conventional chrysanthemum acid esters, and (2) is resistant to organophosphorus insecticides and/or carbide insecticides. (3) It is highly effective against pests that have
On the other hand, they found that it does not have environmental persistence like organic chlorine insecticides, and (4) has extremely low toxicity to humans and animals, leading to the completion of the present invention. Substituted benzyl esters represented by the general formula () can cause damage to paddy rice, field crops, cotton, fruit trees, forests, etc., such as leafhoppers, planthoppers, black beetles, stink bugs, aphids, green caterpillars, fall armyworms, mealybugs, cutworms,
It not only exhibits excellent insecticidal efficacy against agricultural, horticultural and forest pests such as scale insects, leafhoppers, spider mites, silver beetles, white beetles, gypsy moths, and bark beetles, but also against black weevils,
It also has a strong insecticidal effect against grain storage pests such as the snail moth, as well as sanitary pests such as flies, mosquitoes, and cockroaches. Representative substituted benzyl esters represented by the general formula () of the present invention are listed below. Note that these esters include geometric isomers based on the three-dimensional structure of the acid moiety and alcohol moiety, and optical isomers based on the asymmetric carbon atom.
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ã¹ãã¯ãã«ã第ïŒè¡šã«ç€ºãã[Table] Substituted benzyl esters represented by the general formula () are represented by the general formula () A substituted benzyl alcohol or a reactive derivative thereof represented by the general formula () RCOOH...() [wherein R has the same meaning as in the general formula (). ] It can be easily produced by reacting with the carboxylic acid shown in the following formula or a reactive derivative thereof. Here, examples of reactive derivatives of substituted benzyl alcohol include halides and arylsulfonates. Reactive derivatives of carboxylic acids include lower alkyl esters, acid halides, acid anhydrides, alkali metal salts, silver salts, or salts of organic tertiary bases. Below, the above-mentioned typical manufacturing method will be specifically explained. (Production method a) Method by reaction of alcohol and carboxylic acid halide Substituted benzyl alcohol represented by the general formula () and the general formula R COX'' [wherein R has the same meaning as in the general formula (), â³ represents a halogen atom. The carboxylic acid halide represented by ] is preferably a carboxylic acid chloride and a benzene,
By reacting the substituted benzyl alcohol in an inert solvent such as toluene, ether, hexane, or chloroform in the presence of a tertiary amine such as pyridine or triethylamine in an amount of 1 to 3 molar equivalents based on the substituted benzyl alcohol at room temperature or under heating. The desired substituted benzyl ester is obtained. (Production method b) Method by reaction of alcohol and carboxylic acid anhydride Substituted benzyl alcohol represented by the general formula () and the general formula (R CO ) 2 O [wherein R is the general formula ()
has the same meaning as in. ] in an inert solvent such as benzene, toluene, xylene, hexane, acetone, etc.
The desired substituted benzyl ester is preferably obtained by reacting at room temperature or with heating in the presence of an acid such as sulfuric acid or p-toluenesulfonic acid or a tertiary amine such as pyridine or triethylamine. (Production method c) Method by reaction of alcohol and carboxylic acid A substituted benzyl alcohol represented by the general formula () and a carboxylic acid represented by the general formula () are mixed in an inert solvent such as benzene, toluene, or xylene, for example, with dicyclohexyl. carbodiimide,
Alternatively, the desired substituted benzyl ester is obtained by reacting 2-chloro-1-methylpyridinium iodide with a dehydration condensation agent such as triethylamine at room temperature or with heating. (Production method d) Method by reaction of alcohol with lower alkyl ester of carboxylic acid A substituted benzyl alcohol represented by the general formula () and a carboxylic acid represented by the general formula () are transesterified using a suitable transesterification catalyst, such as an alkali metal alkoxide. , in the presence of a titanium metal compound such as sodium hydride or tetramethyl titanate, in an inert solvent such as toluene or xylene, and remove the low-boiling alcohol generated from the reaction system using a rectification column. The desired substituted benzyl ester is obtained by removing . (Manufacturing method e) Method by reaction of alcohol halide or arylsulfonate with alkali metal salt of carboxylic acid Halide or arylsulfonate of substituted benzyl alcohol represented by general formula () and alkali of carboxylic acid represented by general formula () The desired substituted benzyl ester is obtained by reacting the metal salt with the metal salt in a solvent such as dimethylformamide, benzene, or acetone at room temperature or with heating. The substituted benzyl alcohol represented by the general formula (), which is an alcohol component, can be easily and inexpensively produced, for example, by the following method. That is, by ethylating the substituted benzaldehyde represented by the general formula () with sodium acetylide in a liquid ammonia solvent or ethynylating it with ethylmagnesium bromide in a tetrahydrofuran solvent, the substituted benzyl alcohol represented by the general formula () can be obtained. can get. On the other hand, the acid components substituted cyclopropanecarboxylic acid and substituted isovaleric acid are known, and the above-mentioned reactive derivatives of these carboxylic acids can be prepared from the corresponding free acids by conventional methods. When the compound of the present invention is actually applied, it can be used alone without adding other ingredients, but in order to make it easier to use as an insecticide, a carrier may be added to form a preparation. It is generally applied after dilution. For formulation, we use emulsions, wettable powders, powders, granules, fine granules, oils, aerosols, heated fumigants (mosquito coils, electric mosquito repellents, etc.), follicles, etc. in accordance with conventional techniques for agricultural chemical formulations. It can take any form such as aerosols, non-heated fumigants, poison baits, etc., and can be used for various purposes depending on the purpose. In addition, unlike general chrysanthemum acid ester compounds,
The compounds of the present invention have high stability against light, heat, oxidation, etc., but if it is particularly necessary under severe oxidative conditions, antioxidants or ultraviolet absorbers, such as
Phenol derivatives like BHT, BHA, bis-
By adding appropriate amounts of phenol derivatives, arylamines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, condensates of phenetidine and acetone, or benzophenone compounds as stabilizers, compositions with more stable effects can be obtained. Obtainable. The formulation generally contains 0.01 to 95% by weight of the compound of the present invention.
It is preferably contained in an amount of 0.1 to 90% by weight. The compounds of the present invention may be used in the form of the various types of preparations mentioned above, or these preparations may be further formulated into usage forms. The content of the compound of the present invention in the usage form can be appropriately selected within a very wide range such as 0.0000001 to 100% by weight, but is preferably 0.001 to 10% by weight. The insecticides according to the invention are used in the customary manner appropriate to the particular use type. Below, synthesis examples and test examples of the compounds of the present invention,
Although formulation examples and effect examples are shown, the present invention is not limited thereto. In addition, "parts" in the formulation examples mean parts by weight. The compound number is substituted benzyl ester (1) represented by the general formula () above.
- Corresponds to (11). Synthesis Example 1 Cis-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylic acid chloride
2.28 g (0.01 mol) and 1.77 g (0.01 mol) of α-ethynyl-3-nitrobenzyl alcohol were dissolved in 20 ml of dry benzene. Next, 1.58 g (0.02 mol) of pyridine was added dropwise to this solution at room temperature, and the mixture was stirred overnight. Thereafter, the reaction solution was poured into water and extracted with diethyl ether, and the extract was washed with diluted hydrochloric acid water and saturated brine. After drying the organic layer over anhydrous magnesium sulfate, low-boiling substances were distilled off under reduced pressure to obtain a viscous oily product. The obtained product was purified by silica gel high performance liquid chromatography (solvent: n-hexane/isopropyl ether = 85/15 volume ratio) to produce the following:
α-ethynyl-3-nitrobenzyl cis-2,2-dimethyl-3- with NMR spectrum
3.30 g of (2,2-dichlorovinyl)cyclopropanecarboxylate [compound (1), cis form] was obtained (yield 90%). NMR spectrum (90MHz) ÎŽ CDCl3 HMS : 1.13-1.26 (m, 6H); 1.79-2.21 (m, 2H);
2.67-2.72 (m, 1H); 6.13, 6.17 (each d,
1H); 6.45-6.53 (m, 1H); 7.68 (d, 2H);
8.22 (d, 2H) Synthesis Examples 2 to 6 In Synthesis Example 1, trans-2,2 was used instead of 0.01 mol of cis-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylic acid chloride. -dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylic acid chloride, cis-2,2-dimethyl-3-(2,2-dibromvinyl)cyclopropanecarboxylic acid chloride, trans-2,2-dimethyl-3 -(2,2-dibromvinyl)cyclopropanecarboxylic acid chloride, 2,2-dimethyl-3-(2-methyl-1-
Propenyl) cyclopropanecarboxylic acid chloride and α-isopropyl-4-chlorophenylacetic acid chloride were used in the same manner as in Synthesis Example 1, except that 0.01 mol each was used, and the corresponding α-ethynyl-3-nitrobenzyl trans-
2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate [Compound
(1), trans form], α-ethynyl-3-nitrobenzyl cis-2,2-dimethyl-3-(2,2
-Dibromvinyl)cyclopropanecarboxylate [Compound (2), cis form], α-ethynyl-3-
Nitrobenzyl trans-2,2-dimethyl-
3-(2,2-dibromvinyl)cyclopropanecarboxylate [Compound (2), trans form], α
-ethynyl-3-nitrobenzyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate [compound (4)] and α
-ethynyl-3-nitrobenzyl α-isopropyl-4-chlorophenylacetate [compound
(7)] was obtained. Yield and NMR of each product
The spectra are shown in Table 1.
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ã®åçåã³NMRã¹ãã¯ãã«ã第ïŒè¡šã«ç€ºãã[Table] Synthesis Examples 7 to 11 Following the same procedure as Synthesis Example 1, 1.77 g of α-ethynyl-4-nitrobenzyl alcohol
(0.01 mol) to cis-2,2-dimethyl-3-
(2,2-dichlorvinyl)cyclopropanecarboxylic acid chloride, trans-2,2-dimethyl-
3-(2,2-dichlorovinyl)cyclopropanecarboxylic acid chloride, cis-2,2-dimethyl-
3-(2,2-dibromvinyl)cyclopropanecarboxylic acid chloride, 2,2-dimethyl-3-
0.01 mol each of (2-methyl-1-propenyl)cyclopropanecarboxylic acid chloride and α-isopropyl-4-chlorophenylacetic acid chloride were reacted, and the corresponding α-ethynyl-4-nitrobenzyl cis-2,2-dimethyl -3-
(2,2-dichlorvinyl)cyclopropanecarboxylate [compound (8), cis form], α-ethynyl-4-nitrobenzyl trans-2,2-dimethyl-3-(2,2-dichlorvinyl)cyclopropanecarboxylate [Compound (8), trans form], α-ethynyl-4-nitrobenzyl cis-2,2-dimethyl-3-(2,2-dibromvinyl)cyclopropanecarboxylate [compound
(9), cis form], α-ethynyl-4-nitrobenzyl 2,2-dimethyl-3-(2-methyl-1-
Propenyl) cyclopropanecarboxylate [Compound (10)] and α-ethynyl-4-nitrobenzyl α-isopropyl-4-chlorophenylacetate [Compound (11)] were obtained. The yield and NMR spectrum of each product are shown in Table 2.
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ãã[Table] Synthesis Example 12 Following the same procedure as Synthesis Example 1, 1.77 g of α-ethynyl-3-nitrobenzyl alcohol
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-(1,2-dibromo-2,2-dichloroethyl)cyclopropanecarboxylic acid chloride 3.87g
(0.01 mol) was reacted with α-ethynyl-3-nitrobenzyl trans-2,2-dimethyl-3-(1,2-dibromo-2,2-dichloroethyl)cyclopropanecarboxylate having the following NMR spectrum [ Compound (6), trans isomer]
Obtained 4.20g. NMR spectrum (90MHz) ÎŽ CDCl3 HMS : 1.17-1.37 (m, 6H), 1.65-2.45 (m, 2H),
2.69-2.76 (m, 1H), 4.19-4.54 (m, 1H),
6.50 to 6.56 (m, 1H), 7.42 to 8.44 (m, 4H) Test Example 1 Insecticidal test against house flies by microdrop test method Each of the compounds of the present invention and the control compound were accurately weighed as specimens, and an acetone solution of a predetermined concentration was added. Prepared. The above preparation was applied to the dorsal prothorax of an adult female house fly (Musca domestica) anesthetized with ether.
Drop 1Ό and put it in a waist-high shear dish with the bait.
It was covered with a wire mesh lid and stored at a temperature of 25°C. The test insects were sent to 30 insects in one ward. After 24 hours, the test insects were observed to see if they were alive or dead, and the mortality rate was determined. The results are shown in Table 3.
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ã§ãã€ãã[Table] Formulation example 1 Add 50 parts of xylol and 20 parts of the surfactant Nucalgen ST-50 (trade name, Takemoto Yushi Co., Ltd.) to 30 parts of compound (1), and mix well with stirring to obtain 30 parts.
% emulsion was obtained. Formulation example 2 Add 50 parts of xylene and 20 parts of the surfactant Solpol SM-200 (Toho Chemical Industry Co., Ltd., trade name) to 30 parts of compound (1), and mix and dissolve these by stirring well to make a 30% emulsion. I got it. Formulation Example 3 0.5 parts of compound (1) was dissolved in 20 parts of acetone, then 99.5 parts of clay was added and thoroughly stirred, the acetone was removed by evaporation, and 0.5% powder was prepared by further stirring thoroughly in a grinder. Obtained. Formulation Example 4 0.2 part of compound (1) was stirred and dissolved in white kerosene to make a total of 100 parts to obtain an oil solution. Combination example 5 20 parts of compound (1) and surfactant Solpol SM-
200 (same as above) was added and mixed well, and 75 parts of talc was added thereto and sufficiently stirred in a grinder to obtain a wettable powder. Effect Example 1 A 30% emulsion of each of compounds (1) to (11) obtained in the same manner as in Formulation Example 1 was diluted with water to prepare a chemical solution so that the concentration of each compound was 400 ppm. Spray 7 ml/pot of the above chemical solution on rice planted in pots (6 cm diameter pot, 7 rice seedlings) 4 weeks after sowing, air dry, cover with a wire mesh cage, and incubate 20 female adult leafhoppers in the cage. Released. a pot
The test insects were stored in a constant temperature room at 25°C, and after 24 hours, the test insects were observed to see if they were alive or dead, and the mortality rate was determined. In all cases, the mortality rate was over 90%. Effect Example 2 Compounds (1), (2), obtained in the same manner as Formulation Example 1
A chemical solution was prepared by diluting each of the 30% emulsions (4), (5), (8), (9), and (10) with water to give a compound concentration of 40 ppm. Spray 7 ml/pot of the above drug solution on rice planted in pots (6 cm diameter pot, 7 rice seedlings) 4 weeks after sowing, air dry, cover with a wire mesh cage, and incubate 30 female adult leafhoppers in the cage. Released. The pots were stored in a constant temperature room at 25°C, and 24 hours later, the test insects were observed to see if they were alive or dead, and the mortality rate was determined. In all cases, the mortality rate was over 90%. Effect Example 3 Compounds (1) and (8) obtained in the same manner as Formulation Example 1
A drug solution was prepared by diluting each 30% emulsion with water to give a compound concentration of 400 ppm. Spray 7 ml/pot of the above chemical solution on rice planted in pots (pots with a diameter of 6 cm, 7 rice seedlings) 4 weeks after sowing, and after air-drying, cover with a wire mesh cage and release 20 adult brown planthoppers into the cage. I kept it. Pot at 25â
After 24 hours, the test insects were observed to see if they were alive or dead, and the mortality rate was determined. In all cases, the mortality rate was over 90%. Effect Example 4 A 30% emulsion of each of compound (1) and permethrin obtained in the same manner as in Formulation Example 1 was diluted with water to prepare a drug solution so that the concentration of each compound was 40 ppm. Rice planted in pots 4 weeks after sowing (diameter 6
Spray 7 ml/pot of the above chemical solution on 7 cm pots and 7 rice seedlings, and after air-drying, cover with a glass cylinder.
Twenty female adult leafhoppers were released into the cylinder, and the cylinder was covered with gauze. The pots were stored in a constant temperature room at 25°C, and 24 hours later, the test insects were observed to see if they were alive or dead, and the mortality rate was determined. As a result, the mortality rate of compound (1) was 90% or more, and that of permethrin was 60% or less. Effect Example 5 A 30% emulsion of each of compound (1) and permethrin obtained in the same manner as in Formulation Example 2 was diluted with water to prepare a drug solution so that the concentration of each compound was 20 ppm. After immersing the leaves in this chemical solution, air-dry the leaves, place the leaves in a plastic container with a diameter of about 6 cm and a capacity of about 60 cm, and place 3 to 4 diamondback moths in the container.
Ten instar larvae were released. The container was stored in a constant temperature room at 25°C, and two days later, the test insects were observed to see if they were alive or dead, and the mortality rate was determined. The above test was conducted in duplicate. As a result, the mortality rate of compound (1) was 100%, and that of permethrin was 90%.
Claims (1)
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ã¡ãã«åºãè¡šãããã¯ããã²ã³ååãè¡šãããã
ã§ç€ºããã眮æãã³ãžã«ãšã¹ãã«ã ïŒ äžè¬åŒ ãåŒäžãã¯äžè¬åŒ ãåŒãåã¯ãåŒã ã§ç€ºãããåºãè¡šãããããã«R1ã¯
ãåŒãåºåã¯ãåŒãåºãè¡šã ããã¯ããã²ã³ååãè¡šãããåã³Xâ²ã¯å
äžåã¯ç°ãªããåã ããã²ã³ååãè¡šãããå
ã³Yâ²ã¯åäžåã¯ç°ãªããåã ããã²ã³åååã¯
ã¡ãã«åºãè¡šãããã¯ããã²ã³ååãè¡šãããã ã§ç€ºããã眮æãã³ãžã«ãšã¹ãã«ãæå¹æåãšã
ãŠå«æãã殺è«å€ã[Claims] 1. General formula [In the formula, R represents a group represented by the general formula [Formula] or [Formula]. Here, R 1 represents a [formula] group or a [formula] group, Q represents a halogen atom, X and X' are the same or different and each represents a halogen atom, Y and Y' are the same or different and each represents a halogen atom. represents an atom or a methyl group, and Z represents a halogen atom. ]
A substituted benzyl ester represented by 2 General formula [In the formula, R represents a group represented by the general formula [Formula] or [Formula]. Here, R 1 represents a [formula] group or a [formula] group, Q represents a halogen atom, X and X' are the same or different and each represents a halogen atom, Y and Y' are the same or different and each represents a halogen atom. represents an atom or a methyl group, and Z represents a halogen atom. ] An insecticide containing a substituted benzyl ester represented by the following as an active ingredient.
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP55162862A JPS5785304A (en) | 1980-11-18 | 1980-11-18 | Substituted benzyl ester and insecticide containing said ester as active component |
DE19813145448 DE3145448A1 (en) | 1980-11-18 | 1981-11-16 | Substituted benzyl ester of a 2,2-dimethyl-3-(2,2-dihalovinyl)- cyclopropanecarboxylic acid, pesticidal agents containing it, and the control of pests |
GB8134572A GB2088369B (en) | 1980-11-18 | 1981-11-17 | Pesticidal substituted benzyl esters of 2, 2-dimethyl-3-(2, 2-dihalovinyl) cyclopropanecarboxilic acid |
FR8121512A FR2494266A1 (en) | 1980-11-18 | 1981-11-17 | BENZYL ESTER SUBSTITUTED WITH 2,2-DIMETHYL-3- (2,2-DIHALOVINYL) CYCLOPROPANECARBOXYLIC ACID, PESTICIDAL COMPOSITION CONTAINING THE ESTER AS AN ACTIVE INGREDIENT AND METHOD OF USING THE ESTER AS A PESTICIDE |
CH7416/81A CH647224A5 (en) | 1980-11-18 | 1981-11-18 | SUBSTITUTED BENZYL ESTER OF A 2,2-DIMETHYL-3- (2,2-DIHALOGENVINYL) CYCLOPROPANCARBONIC ACID. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP55162862A JPS5785304A (en) | 1980-11-18 | 1980-11-18 | Substituted benzyl ester and insecticide containing said ester as active component |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP56060047A Division JPS5788150A (en) | 1980-11-18 | 1981-04-20 | Substituted benzyl ester and insecticide containing the same as active constituent |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5785304A JPS5785304A (en) | 1982-05-28 |
JPH0135819B2 true JPH0135819B2 (en) | 1989-07-27 |
Family
ID=15762661
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP55162862A Granted JPS5785304A (en) | 1980-11-18 | 1980-11-18 | Substituted benzyl ester and insecticide containing said ester as active component |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5785304A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58144349A (en) * | 1982-02-22 | 1983-08-27 | Sumitomo Chem Co Ltd | Its preparation and carboxylic ester, insecticide, acaricide containing the same |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS505530A (en) * | 1973-05-24 | 1975-01-21 | ||
JPS5035332A (en) * | 1973-07-30 | 1975-04-04 |
-
1980
- 1980-11-18 JP JP55162862A patent/JPS5785304A/en active Granted
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS505530A (en) * | 1973-05-24 | 1975-01-21 | ||
JPS5035332A (en) * | 1973-07-30 | 1975-04-04 |
Also Published As
Publication number | Publication date |
---|---|
JPS5785304A (en) | 1982-05-28 |
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