US3316145A - O, o-dimethyl s-(1-succinimidoethyl) phos-phorodithioate and insecticidal compositions containing the same - Google Patents
O, o-dimethyl s-(1-succinimidoethyl) phos-phorodithioate and insecticidal compositions containing the same Download PDFInfo
- Publication number
- US3316145A US3316145A US424843A US42484365A US3316145A US 3316145 A US3316145 A US 3316145A US 424843 A US424843 A US 424843A US 42484365 A US42484365 A US 42484365A US 3316145 A US3316145 A US 3316145A
- Authority
- US
- United States
- Prior art keywords
- dimethyl
- succinimidoethyl
- concentrate
- toxicant
- phosphorodithioate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title description 7
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 title description 5
- 230000000749 insecticidal effect Effects 0.000 title description 4
- 230000000694 effects Effects 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- UCOYLBXWLBXMGZ-UHFFFAOYSA-N 1-(1-dihydroxyphosphinothioylsulfanylethyl)pyrrolidine-2,5-dione Chemical compound CC(N1C(=O)CCC1=O)SP(=S)(O)O UCOYLBXWLBXMGZ-UHFFFAOYSA-N 0.000 claims description 2
- 231100000167 toxic agent Toxicity 0.000 description 20
- 239000003440 toxic substance Substances 0.000 description 20
- 235000008504 concentrate Nutrition 0.000 description 19
- 239000012141 concentrate Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000000839 emulsion Substances 0.000 description 17
- 239000002917 insecticide Substances 0.000 description 15
- 239000004094 surface-active agent Substances 0.000 description 15
- 239000002671 adjuvant Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 241000238631 Hexapoda Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000428 dust Substances 0.000 description 6
- 235000014666 liquid concentrate Nutrition 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 231100000419 toxicity Toxicity 0.000 description 6
- 230000001988 toxicity Effects 0.000 description 6
- 241000255925 Diptera Species 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- -1 1-succinimidoethyl Chemical group 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VOCDJQSAMZARGX-UHFFFAOYSA-N 1-ethenylpyrrolidine-2,5-dione Chemical compound C=CN1C(=O)CCC1=O VOCDJQSAMZARGX-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 2
- 241000238876 Acari Species 0.000 description 1
- 241000253994 Acyrthosiphon pisum Species 0.000 description 1
- 244000045232 Canavalia ensiformis Species 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 241000532642 Conotrachelus nenuphar Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- CZGGKXNYNPJFAX-UHFFFAOYSA-N Dimethyldithiophosphate Chemical compound COP(S)(=S)OC CZGGKXNYNPJFAX-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000462639 Epilachna varivestis Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- 235000010617 Phaseolus lunatus Nutrition 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229910000286 fullers earth Inorganic materials 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/5537—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom the heteroring containing the structure -C(=O)-N-C(=O)- (both carbon atoms belong to the heteroring)
-
- 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
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
Definitions
- 0,0-dimethyl S'(1-succinimidoethyl) phosphorodithioate is a biodegradable insecticide having a long residual toxicity.
- Example 1 To 38 parts of N-vinyl succinimide in 40 parts of benzene was added 53.7 parts dimethyl dithiophosphoric acid in about parts of benzene dropwise over a 0.5 hour period. The resulting solution was heated at 80 C. under reflux for 6 hours, cooled and washed at 35 C. with water and 5% aqueous sodium bicarbonate solution. On cooling below room temperature, 39.3 parts crystalline product separated. After distilling off the benzene and adding a little ether, an additional crop of 30.5 parts crystalline product was obtained.
- the reaction between the N-vinyl succinimide and 0,0-dimethyl dithiophosphoric acid takes place at a temperature within the range of 25-l20 C.
- the reaction between N-a-chloroethyl succinimide and 0,0-dimethyl dithiophosphoric acid, or a salt thereof such as the ammonium salt, also yields the product of this invention.
- Solvents for the latter reaction include acetone and acetonitrile in addition to benzene or toluene.
- the 0,0-dimethyl S-( l-succinimidoethyl) phosphorodithioate of this invention is useful as a toxicant in insecticide compositions for many types of insects and is used preferably as a dust or as an aqueous emulsion.
- Dusts are formulated from a dust concentrate or from It is common practice for a formulator to dilute a dust concentrate with a clay or similar powdered solid to the desired dilution for application.
- the dust concentrate when compounded with a wetting Ialgent, is a wettable powder, which is emulsifiable in the eld.
- Aqueous emulsions are formulated by a formulator from a liquid concentrate.
- the formulator will use either a liquid concentrate containing the toxicant and a surface-active dispersing agent, or a liquid concentrate, water, and a surface-active agent.
- a liquid concentrate containing a surface-active agent will be used by the man in the field who wishes to prepare aqueous emulsions economically.
- the concentrate is preferably a composition of the toxicant of this invention and a non-volatile adjuvant which is solid, as in the case of dusts, or is liquid, as in the case here an aqueous emulsion is produced or in the case here a formulator mixes the liquid concentrate with dust v form a more dilute dust.
- a concentrate of toxicant 1d a volatile adjuvant such as a volatile organic solvent ill be useful also for combination with a surface-active djuvant by a formulator of concentrates.
- the concentration of the toxicant in a concentrate will e 10-90% in the case where a volatile organic solvent used, and 25-90% where there is no volatile organic olvent.
- the solid adjuvant of the composition is selected accordinging to the properties desired from such solids as :lays, fullers earth, diatomaceous earth, rosin, petroleum iydrocarbon insoluble pine wood resins, and surfaceictive dispersing agents.
- the solid adjuvant will thus in nany cases have surface-active, spreading or sticking properties and, in some cases, will be used with water or organic solvent to aid in the mixing process.
- the liquid adjuvant of the composition is selected from the non-volatile liquids such as petroleum oils, paraffin, oils, lubricating oils and rosin oils, and volatile liquids such as toluene, benzene, Xylenes, volatile petroleum fractions, acetone, methyl ethyl ketone, and diacetone alcohol.
- non-volatile liquids such as petroleum oils, paraffin, oils, lubricating oils and rosin oils
- volatile liquids such as toluene, benzene, Xylenes, volatile petroleum fractions, acetone, methyl ethyl ketone, and diacetone alcohol.
- the concentrate containing a surface-active agent will contain usually 0.01 to 2 times as much surface-active agent as toxicant and other components to be dispersed in formation of an aqueous emulsion, and preferably 0.05 to 0.5 times as much surface-active agent as material to be dispersed.
- the concentrate which is a solution of all components such as a concentrate of toxicant and surfaceactive agent which is soluble in organic solvents preferably also contains a volatile organic solvent in an amount in the range of 0.1 to 10 times the weight of toxicant when necessary to improve fluidity.
- the concentrate of toxicant and liquid non-volatile adjuvant generally contains 5-25% surface-active agent to aid in emulsification.
- a concentrate containing a surface-active agent is, by well known technique, formed into water-in-oil or oil-in-water emulsions. For the former, -25% surface-active agent is used and, for the latter, -20% is used.
- a concentrate containing toxicant, non-volatile adjuvant, and surface-active agent is emulsified in the field without further diluting but it is, at times, advantageous to dilute this concentrate with oil containing a surface-active agent when it is desired to obtain dilute water-in-oil, i.e., invert, emulsions.
- the surface-active agents which are used are any of those anionic, cationic or non-ionic surface-active agents well known in the art. See Chemistry of Insecticides, Fungicides and Herbicides (Donald E. H. Frear, 2nd ed. 194-8, pages 280-7).
- the surface-active agents which are particularly suitable are the polyoxyethylene compounds such as reaction products of alcohols or amines with ethylene oxide. Other surface-active agents and methods of using them for various types of emulsions are to be found in Surface Active Agents-Their Chem istry and Technology, Anthony M. Schwartz and James W. Perry, Interscience Publishers Inc., New York, 1949,
- a concentrate of equal parts each of acetone, 0,0- dimethyl S-(l-succinimidoethyl) phosphorodithioate and Tween 20 was prepared and added to distilled water, with rapid stirring, to form emulsions of various concentrations from 0.05% to 0.0005% toxicant.
- a 0.025% emulsion gave kill of housefiies.
- An 0.0025% emulsion gave a 100% kill of Mexican bean beetle.
- a 0.005% emulsion gave a 100% kill of pea aphids.
- a 0.0005 emulsion gave a 100% kill of two-spotted mites.
- the residual activity shows the superiority of the toxicant of this invention when applied to the habitats of mosquitoes.
- the toxicant of this invention while high in residual activity on the habitats of many insects, is nevertheless not in the persistent class since it is biodegradable, for example, in soil.
- the 0,0-dimethyl S-(l-succinimidoethyl) phosphorodithioate of this invention can be used in combination with other insecticides where desired.
- the other insecticide need not be biodegradable since the biodegradability of the present insecticide will act as an improver of the properties of the combination.
- An insecticide concentrate comprising 0,0-dimethyl S-(l-succinimidoethyl) phosphorodithioate as a toxicant and a non-volatile dispersing adjuvant therefor.
- An insecticide concentrate comprising 0,0-dimethy1 S-(l-succinimidoethyl) phosphorodithioate as -a toxicant and a solid non-volatile dispersing adjuvant therefor.
- An insecticide concentrate comprising 0,0-dimethyl S-(l-succinimidoethyl) phosphorodithioate as a toxicant and a surface-active dispersing agent in an amount effective for dispersing the toxicant in water.
- An insecticide concentrate comprising 0,0-dimethyl S-(l-succinimidoethyl) phosphorodithioate as a toXicant, an organic solvent for the toxicant and a surface-active dispersing agent soluble in said solvent in an amount effective for dispersing the toxicant in water.
- An aqueous emulsion comprising a major amount of water and a minor but insecticidally effective amount of 0,0-dimethyl S-(l-succinimidoethyl) phosphorodithioate and a surface-active dispersing agent.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US424843A US3316145A (en) | 1965-01-11 | 1965-01-11 | O, o-dimethyl s-(1-succinimidoethyl) phos-phorodithioate and insecticidal compositions containing the same |
| IL24877A IL24877A (en) | 1965-01-11 | 1965-12-27 | O,o-dimethyl s-(alpha-succinimidoethyl)phosphorodithioate and insecticidal compositions containing the same |
| GB556/66A GB1098548A (en) | 1965-01-11 | 1966-01-05 | An organic phosphorodithioate compound |
| FR46803A FR1469250A (fr) | 1965-01-11 | 1966-01-07 | omicron, omicron-diméthyl s-(1-succinimidoéthyl) phosphorodithioate et composition insecticide le contenant |
| NL6600295A NL6600295A (US06534493-20030318-C00166.png) | 1965-01-11 | 1966-01-10 | |
| ES0321588A ES321588A1 (es) | 1965-01-11 | 1966-01-10 | Un procedimiento para preparar una composicion insecticida. |
| BE674914D BE674914A (US06534493-20030318-C00166.png) | 1965-01-11 | 1966-01-10 | |
| CH31166A CH453790A (fr) | 1965-01-11 | 1966-01-11 | Composition insecticide |
| DE19661695128 DE1695128A1 (de) | 1965-01-11 | 1966-01-11 | Schaedlingsbekaempfungsmittel |
| CH26768A CH500229A (fr) | 1965-01-11 | 1966-01-11 | Procédé de préparation du O,O-diméthyl-S-(1-succinimidoéthyl)-phosphorodithioate |
| DK13966AA DK124411B (da) | 1965-01-11 | 1966-01-11 | Fosfordithioat til anvendelse i insekticider. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US424843A US3316145A (en) | 1965-01-11 | 1965-01-11 | O, o-dimethyl s-(1-succinimidoethyl) phos-phorodithioate and insecticidal compositions containing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3316145A true US3316145A (en) | 1967-04-25 |
Family
ID=23684094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US424843A Expired - Lifetime US3316145A (en) | 1965-01-11 | 1965-01-11 | O, o-dimethyl s-(1-succinimidoethyl) phos-phorodithioate and insecticidal compositions containing the same |
Country Status (10)
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE930446C (de) * | 1953-02-09 | 1955-07-18 | Bayer Ag | Verfahren zur Herstellung von Thiophosphorsaeureestern |
| US2902493A (en) * | 1955-05-13 | 1959-09-01 | Bayer Ag | Thiophosphoric acid esters and process for their production |
| GB869399A (en) * | 1958-07-15 | 1961-05-31 | Basf Ag | O.o-dialkyl-thiol-and o.o-dialkyl-dithio-phosphoric acid esters of lactams and thiolactams |
-
1965
- 1965-01-11 US US424843A patent/US3316145A/en not_active Expired - Lifetime
- 1965-12-27 IL IL24877A patent/IL24877A/en unknown
-
1966
- 1966-01-05 GB GB556/66A patent/GB1098548A/en not_active Expired
- 1966-01-07 FR FR46803A patent/FR1469250A/fr not_active Expired
- 1966-01-10 BE BE674914D patent/BE674914A/xx unknown
- 1966-01-10 NL NL6600295A patent/NL6600295A/xx unknown
- 1966-01-10 ES ES0321588A patent/ES321588A1/es not_active Expired
- 1966-01-11 DK DK13966AA patent/DK124411B/da unknown
- 1966-01-11 CH CH31166A patent/CH453790A/fr unknown
- 1966-01-11 DE DE19661695128 patent/DE1695128A1/de active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE930446C (de) * | 1953-02-09 | 1955-07-18 | Bayer Ag | Verfahren zur Herstellung von Thiophosphorsaeureestern |
| US2902493A (en) * | 1955-05-13 | 1959-09-01 | Bayer Ag | Thiophosphoric acid esters and process for their production |
| GB869399A (en) * | 1958-07-15 | 1961-05-31 | Basf Ag | O.o-dialkyl-thiol-and o.o-dialkyl-dithio-phosphoric acid esters of lactams and thiolactams |
Also Published As
| Publication number | Publication date |
|---|---|
| IL24877A (en) | 1969-11-12 |
| DE1695128A1 (de) | 1970-12-10 |
| GB1098548A (en) | 1968-01-10 |
| BE674914A (US06534493-20030318-C00166.png) | 1966-07-11 |
| CH453790A (fr) | 1968-03-31 |
| ES321588A1 (es) | 1967-01-01 |
| FR1469250A (fr) | 1967-02-10 |
| DK124411B (da) | 1972-10-16 |
| NL6600295A (US06534493-20030318-C00166.png) | 1966-07-12 |
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