IL33731A - O,o-dialkyl-s-(1,2,2-trichloroethyl)-thionothiolphosphoric acid esters and o-alkyl-s-(1,2,2-trichloroethyl)-alkane-thionothiolphosphonic acid esters,their preparation and use as insecticides - Google Patents
O,o-dialkyl-s-(1,2,2-trichloroethyl)-thionothiolphosphoric acid esters and o-alkyl-s-(1,2,2-trichloroethyl)-alkane-thionothiolphosphonic acid esters,their preparation and use as insecticidesInfo
- Publication number
- IL33731A IL33731A IL33731A IL3373170A IL33731A IL 33731 A IL33731 A IL 33731A IL 33731 A IL33731 A IL 33731A IL 3373170 A IL3373170 A IL 3373170A IL 33731 A IL33731 A IL 33731A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- carbon atoms
- formula
- alkyl
- acid
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 27
- 150000002148 esters Chemical class 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title description 19
- 239000002917 insecticide Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 84
- 241000238631 Hexapoda Species 0.000 claims description 33
- 239000002904 solvent Substances 0.000 claims description 25
- 239000002689 soil Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- -1 1,2, 2-trichloroethyl Chemical group 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 239000003085 diluting agent Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 230000006378 damage Effects 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 230000000749 insecticidal effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
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- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000004490 chloroalkoxy group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
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- 239000003995 emulsifying agent Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 241000255925 Diptera Species 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- TYQTYRXEMJXFJG-UHFFFAOYSA-N phosphorothious acid Chemical compound OP(O)S TYQTYRXEMJXFJG-UHFFFAOYSA-N 0.000 description 6
- 229920000151 polyglycol Polymers 0.000 description 6
- 239000010695 polyglycol Substances 0.000 description 6
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- 238000009472 formulation Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
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- 238000009835 boiling Methods 0.000 description 4
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- HPWUIVNEYXRBJW-UHFFFAOYSA-N 1,2,2-trichloroethyl thiohypochlorite Chemical compound ClC(C(Cl)Cl)SCl HPWUIVNEYXRBJW-UHFFFAOYSA-N 0.000 description 3
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
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- 125000000129 anionic group Chemical group 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
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- 150000002170 ethers Chemical class 0.000 description 1
- GYUULSJUCGKHOW-UHFFFAOYSA-N ethoxy(ethyl)phosphinothious acid Chemical compound C(C)OP(S)CC GYUULSJUCGKHOW-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- KAKYPBMWXLFJOS-UHFFFAOYSA-N ethyl(methoxy)phosphinothious acid Chemical compound COP(S)CC KAKYPBMWXLFJOS-UHFFFAOYSA-N 0.000 description 1
- KVLYFRSZXOEDRC-UHFFFAOYSA-N ethyl(propan-2-yloxy)phosphinothious acid Chemical compound C(C)(C)OP(S)CC KVLYFRSZXOEDRC-UHFFFAOYSA-N 0.000 description 1
- ZVDMGTXNNVGAAO-UHFFFAOYSA-N ethyl(sulfanyl)phosphinous acid Chemical compound C(C)P(O)S ZVDMGTXNNVGAAO-UHFFFAOYSA-N 0.000 description 1
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- 230000002464 fungitoxic effect Effects 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
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- 150000002367 halogens Chemical class 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
- A01N57/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34 containing acyclic or cycloaliphatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4078—Esters with unsaturated acyclic alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691905356 DE1905356A1 (de) | 1969-02-04 | 1969-02-04 | O,O-Dialkyl-S-(1,2,2-trichloraethyl)-thionothiolphosphor- bzw.O-Alkyl-S-(1,2,2-trichloraethyl)-alkanthionothiolphosphonsaeureester und Verfahren zu ihrer Herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL33731A0 IL33731A0 (en) | 1970-03-22 |
| IL33731A true IL33731A (en) | 1972-11-28 |
Family
ID=5724239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL33731A IL33731A (en) | 1969-02-04 | 1970-01-19 | O,o-dialkyl-s-(1,2,2-trichloroethyl)-thionothiolphosphoric acid esters and o-alkyl-s-(1,2,2-trichloroethyl)-alkane-thionothiolphosphonic acid esters,their preparation and use as insecticides |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3732341A (ja) |
| JP (1) | JPS4818808B1 (ja) |
| AT (1) | AT297025B (ja) |
| BE (1) | BE745483A (ja) |
| BG (1) | BG17694A3 (ja) |
| BR (1) | BR7016563D0 (ja) |
| CH (1) | CH494776A (ja) |
| DE (1) | DE1905356A1 (ja) |
| DK (1) | DK125328B (ja) |
| ES (1) | ES376150A1 (ja) |
| FR (1) | FR2033959A5 (ja) |
| GB (1) | GB1245735A (ja) |
| IL (1) | IL33731A (ja) |
| NL (1) | NL7001524A (ja) |
| RO (1) | RO56241A (ja) |
| SE (1) | SE352089B (ja) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4013793A (en) * | 1970-03-13 | 1977-03-22 | Nihon Tokushu Noyaku Seizo Kabushiki Kaisha | Combating pests with o-ethyl-s-propyl-thionothiol or dithiophosphoric acid phenyl or naphthyl esters |
| US3898334A (en) * | 1970-03-13 | 1975-08-05 | Bayer Ag | Pesticidal o-ethyl-S-propyl-dithiophosphoric acid phenyl or naphthyl esters |
| US4866045A (en) * | 1984-04-30 | 1989-09-12 | E. I. Du Pont Nemours And Company | Tetrachloroethyl phosphorothioate soil insecticide |
| JPH0217207Y2 (ja) * | 1985-12-24 | 1990-05-14 |
-
1969
- 1969-02-04 DE DE19691905356 patent/DE1905356A1/de active Pending
-
1970
- 1970-01-16 CH CH64570A patent/CH494776A/de not_active IP Right Cessation
- 1970-01-19 IL IL33731A patent/IL33731A/en unknown
- 1970-01-26 GB GB3668/70A patent/GB1245735A/en not_active Expired
- 1970-01-27 BG BG013825A patent/BG17694A3/xx unknown
- 1970-01-27 SE SE00994/70A patent/SE352089B/xx unknown
- 1970-01-27 DK DK38770AA patent/DK125328B/da unknown
- 1970-01-30 US US00007263A patent/US3732341A/en not_active Expired - Lifetime
- 1970-02-02 RO RO62322A patent/RO56241A/ro unknown
- 1970-02-03 ES ES376150A patent/ES376150A1/es not_active Expired
- 1970-02-03 NL NL7001524A patent/NL7001524A/xx unknown
- 1970-02-04 BR BR216563/70A patent/BR7016563D0/pt unknown
- 1970-02-04 BE BE745483D patent/BE745483A/xx unknown
- 1970-02-04 FR FR7003969A patent/FR2033959A5/fr not_active Expired
- 1970-02-04 AT AT99670A patent/AT297025B/de not_active IP Right Cessation
- 1970-02-04 JP JP45009349A patent/JPS4818808B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH494776A (de) | 1970-08-15 |
| SE352089B (ja) | 1972-12-18 |
| AT297025B (de) | 1972-03-10 |
| BR7016563D0 (pt) | 1973-04-05 |
| RO56241A (ja) | 1974-06-01 |
| BG17694A3 (bg) | 1973-12-25 |
| BE745483A (fr) | 1970-08-04 |
| ES376150A1 (es) | 1972-03-16 |
| DE1905356A1 (de) | 1970-08-06 |
| FR2033959A5 (ja) | 1970-12-04 |
| IL33731A0 (en) | 1970-03-22 |
| US3732341A (en) | 1973-05-08 |
| JPS4818808B1 (ja) | 1973-06-08 |
| GB1245735A (en) | 1971-09-08 |
| NL7001524A (ja) | 1970-08-06 |
| DK125328B (da) | 1973-02-05 |
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