JPS5953241B2 - だにあるいは害虫の防除法 - Google Patents
だにあるいは害虫の防除法Info
- Publication number
- JPS5953241B2 JPS5953241B2 JP50022710A JP2271075A JPS5953241B2 JP S5953241 B2 JPS5953241 B2 JP S5953241B2 JP 50022710 A JP50022710 A JP 50022710A JP 2271075 A JP2271075 A JP 2271075A JP S5953241 B2 JPS5953241 B2 JP S5953241B2
- Authority
- JP
- Japan
- Prior art keywords
- thiophene
- phenylthio
- mol
- drug
- diphenylthiophene
- 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
- 241000238876 Acari Species 0.000 title claims description 22
- 241000607479 Yersinia pestis Species 0.000 title claims description 9
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 83
- 229930192474 thiophene Natural products 0.000 claims description 50
- -1 phenylsulfono Chemical group 0.000 claims description 33
- 150000003577 thiophenes Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 230000000895 acaricidal effect Effects 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 239000000460 chlorine Chemical group 0.000 claims description 7
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 241000238631 Hexapoda Species 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 230000000749 insecticidal effect Effects 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 32
- 239000003814 drug Substances 0.000 description 31
- 229940079593 drug Drugs 0.000 description 31
- 239000000203 mixture Substances 0.000 description 18
- 238000012360 testing method Methods 0.000 description 17
- 241000196324 Embryophyta Species 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 14
- 238000005259 measurement Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- JWUKZUIGOJBEPC-UHFFFAOYSA-N phenyl thiohypochlorite Chemical compound ClSC1=CC=CC=C1 JWUKZUIGOJBEPC-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000238421 Arthropoda Species 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 240000008042 Zea mays Species 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- FKHVUWRLXRMJLF-UHFFFAOYSA-N 2,4-diphenylthiophene Chemical compound C=1SC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 FKHVUWRLXRMJLF-UHFFFAOYSA-N 0.000 description 4
- SYAUXTHXMQIDNC-UHFFFAOYSA-N 2-(3,4-dimethylphenyl)thiophene Chemical compound C1=C(C)C(C)=CC=C1C1=CC=CS1 SYAUXTHXMQIDNC-UHFFFAOYSA-N 0.000 description 4
- AFLBPIABCXIKBD-UHFFFAOYSA-N 2-(4-methylsulfanylphenyl)thiophene Chemical compound C1=CC(SC)=CC=C1C1=CC=CS1 AFLBPIABCXIKBD-UHFFFAOYSA-N 0.000 description 4
- IIUDZDPILDMBFH-UHFFFAOYSA-N 2-(4-propan-2-ylphenyl)thiophene Chemical compound C1=CC(C(C)C)=CC=C1C1=CC=CS1 IIUDZDPILDMBFH-UHFFFAOYSA-N 0.000 description 4
- PJRGDKFLFAYRBV-UHFFFAOYSA-N 2-phenylthiophene Chemical compound C1=CSC(C=2C=CC=CC=2)=C1 PJRGDKFLFAYRBV-UHFFFAOYSA-N 0.000 description 4
- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- QIQRZPZOOFRYRL-UHFFFAOYSA-N 2,3,5-triphenylthiophene Chemical compound C1=C(C=2C=CC=CC=2)SC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 QIQRZPZOOFRYRL-UHFFFAOYSA-N 0.000 description 3
- UUBWNOWUMQHZJH-UHFFFAOYSA-N 2-(4-methylphenyl)-5-phenylsulfanylthiophene Chemical compound C1=CC(C)=CC=C1C(S1)=CC=C1SC1=CC=CC=C1 UUBWNOWUMQHZJH-UHFFFAOYSA-N 0.000 description 3
- GGJDJCBJLDHXEZ-UHFFFAOYSA-N 2-phenyl-5-phenylsulfanylthiophene Chemical compound C=1C=CC=CC=1SC(S1)=CC=C1C1=CC=CC=C1 GGJDJCBJLDHXEZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000642 acaricide Substances 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- HWKZNRABKQDKTC-UHFFFAOYSA-N 2,5-diphenylthiophene Chemical compound C=1C=C(C=2C=CC=CC=2)SC=1C1=CC=CC=C1 HWKZNRABKQDKTC-UHFFFAOYSA-N 0.000 description 2
- SDZYNDZWHGOSHW-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-phenylsulfanylthiophene Chemical compound ClC1=CC=CC(C=2SC(SC=3C=CC=CC=3)=CC=2)=C1 SDZYNDZWHGOSHW-UHFFFAOYSA-N 0.000 description 2
- VJWXOAYXNHDRQZ-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenyl]thiophene Chemical compound FC(F)(F)C1=CC=CC(C=2SC=CC=2)=C1 VJWXOAYXNHDRQZ-UHFFFAOYSA-N 0.000 description 2
- MSFYGFCSVXTEEM-UHFFFAOYSA-N 2-nitro-3,5-diphenylthiophene Chemical compound [N+](=O)([O-])C=1SC(=CC=1C1=CC=CC=C1)C1=CC=CC=C1 MSFYGFCSVXTEEM-UHFFFAOYSA-N 0.000 description 2
- WFKYHWLFRXTVOF-UHFFFAOYSA-N 2-phenylsulfanyl-5-(4-propan-2-ylphenyl)thiophene Chemical compound C1=CC(C(C)C)=CC=C1C(S1)=CC=C1SC1=CC=CC=C1 WFKYHWLFRXTVOF-UHFFFAOYSA-N 0.000 description 2
- XPAHGZVGGQYPDY-UHFFFAOYSA-N 2-phenylsulfanyl-5-[3-(trifluoromethyl)phenyl]thiophene Chemical compound FC(F)(F)C1=CC=CC(C=2SC(SC=3C=CC=CC=3)=CC=2)=C1 XPAHGZVGGQYPDY-UHFFFAOYSA-N 0.000 description 2
- VWRSEKJUUSZKSH-UHFFFAOYSA-N 3,5-diphenyl-2-phenylsulfanylthiophene Chemical compound C=1C=CC=CC=1SC=1SC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 VWRSEKJUUSZKSH-UHFFFAOYSA-N 0.000 description 2
- 241000256118 Aedes aegypti Species 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000219146 Gossypium Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 244000141359 Malus pumila Species 0.000 description 2
- 241000219094 Vitaceae Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 238000006254 arylation reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
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- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
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- 239000002023 wood Substances 0.000 description 2
- GBIYAVWBYTZRNJ-UHFFFAOYSA-N (3-nitrophenyl) thiohypochlorite Chemical compound [O-][N+](=O)C1=CC=CC(SCl)=C1 GBIYAVWBYTZRNJ-UHFFFAOYSA-N 0.000 description 1
- WVTOJNFZIVWNIY-UHFFFAOYSA-N (4-chlorophenyl) thiohypochlorite Chemical compound ClSC1=CC=C(Cl)C=C1 WVTOJNFZIVWNIY-UHFFFAOYSA-N 0.000 description 1
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- APJZNEIPPWWGLM-UHFFFAOYSA-N 2,5-bis(phenylsulfanyl)thiophene Chemical compound C=1C=CC=CC=1SC(S1)=CC=C1SC1=CC=CC=C1 APJZNEIPPWWGLM-UHFFFAOYSA-N 0.000 description 1
- PITSXXFDQLCAGC-UHFFFAOYSA-N 2-(3,4-dimethylphenyl)-5-phenylsulfanylthiophene Chemical compound C1=C(C)C(C)=CC=C1C(S1)=CC=C1SC1=CC=CC=C1 PITSXXFDQLCAGC-UHFFFAOYSA-N 0.000 description 1
- OHOZYQHIKDVRQX-UHFFFAOYSA-N 2-(3-chlorophenyl)sulfanyl-3,5-diphenylthiophene Chemical compound ClC1=CC=CC(SC2=C(C=C(S2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 OHOZYQHIKDVRQX-UHFFFAOYSA-N 0.000 description 1
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- KXWVWGDIKZWGKU-UHFFFAOYSA-N 2-(benzenesulfonyl)-5-phenylthiophene Chemical compound C=1C=CC=CC=1S(=O)(=O)C(S1)=CC=C1C1=CC=CC=C1 KXWVWGDIKZWGKU-UHFFFAOYSA-N 0.000 description 1
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- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 208000007865 relapsing fever Diseases 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 201000004284 spotted fever Diseases 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CHXZRHMQQRUVHF-UHFFFAOYSA-N thiophene A Natural products CC#CC1=CC=C(C#CC#CC=C)S1 CHXZRHMQQRUVHF-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/42—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms with nitro or nitroso radicals directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44537874A | 1974-02-25 | 1974-02-25 | |
| US445378 | 1974-02-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS50117922A JPS50117922A (enrdf_load_html_response) | 1975-09-16 |
| JPS5953241B2 true JPS5953241B2 (ja) | 1984-12-24 |
Family
ID=23768674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50022710A Expired JPS5953241B2 (ja) | 1974-02-25 | 1975-02-24 | だにあるいは害虫の防除法 |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5953241B2 (enrdf_load_html_response) |
| FR (1) | FR2261704A1 (enrdf_load_html_response) |
| ZA (1) | ZA75270B (enrdf_load_html_response) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4778819A (en) * | 1988-01-27 | 1988-10-18 | Uniroyal Chemical Company, Inc. | 2-(tetrahydro-2-thienyl)phenols and carbamate derivatives thereof |
-
1975
- 1975-01-14 ZA ZA00750270A patent/ZA75270B/xx unknown
- 1975-02-20 FR FR7505314A patent/FR2261704A1/fr not_active Withdrawn
- 1975-02-24 JP JP50022710A patent/JPS5953241B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2261704A1 (enrdf_load_html_response) | 1975-09-19 |
| JPS50117922A (enrdf_load_html_response) | 1975-09-16 |
| ZA75270B (en) | 1976-04-28 |
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