US3361855A - Dithiophosphonic acid esters - Google Patents
Dithiophosphonic acid esters Download PDFInfo
- Publication number
- US3361855A US3361855A US88026A US8802661A US3361855A US 3361855 A US3361855 A US 3361855A US 88026 A US88026 A US 88026A US 8802661 A US8802661 A US 8802661A US 3361855 A US3361855 A US 3361855A
- Authority
- US
- United States
- Prior art keywords
- yield
- solutions
- mol
- killed
- added
- 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
- FLQUDUCNBDGCRI-UHFFFAOYSA-N hydroxy-sulfanyl-sulfidophosphanium Chemical class SP(S)=O FLQUDUCNBDGCRI-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 22
- 239000000243 solution Substances 0.000 description 39
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 9
- 241001124076 Aphididae Species 0.000 description 8
- 241000256113 Culicidae Species 0.000 description 8
- 241000700159 Rattus Species 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 241000255925 Diptera Species 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 241001454295 Tetranychidae Species 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VZXOZSQDJJNBRC-UHFFFAOYSA-N 4-chlorobenzenethiol Chemical compound SC1=CC=C(Cl)C=C1 VZXOZSQDJJNBRC-UHFFFAOYSA-N 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 125000000068 chlorophenyl group Chemical group 0.000 description 4
- 235000019256 formaldehyde Nutrition 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 2
- 241000239290 Araneae Species 0.000 description 2
- MHOWCHQNHPCPOE-UHFFFAOYSA-N CCP(O)(OC)=S.Cl Chemical compound CCP(O)(OC)=S.Cl MHOWCHQNHPCPOE-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 241000488583 Panonychus ulmi Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- -1 chalk Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000003151 ovacidal effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- WLHCBQAPPJAULW-UHFFFAOYSA-N 4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1 WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241000256111 Aedes <genus> Species 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- MGJNTCKRAHBWDM-UHFFFAOYSA-N CCOP(C=C(C)C)(O)=S.Cl Chemical compound CCOP(C=C(C)C)(O)=S.Cl MGJNTCKRAHBWDM-UHFFFAOYSA-N 0.000 description 1
- WEQVLSZDHCLFPN-UHFFFAOYSA-N COP(C)(O)=S.Cl Chemical compound COP(C)(O)=S.Cl WEQVLSZDHCLFPN-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001300479 Macroptilium Species 0.000 description 1
- 241000219833 Phaseolus Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 1
- BFHXKSJAKWIQQW-UHFFFAOYSA-N ethyl-methoxy-phenylsulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCP(=S)(OC)SC1=CC=CC=C1 BFHXKSJAKWIQQW-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000013519 translation Methods 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
- C07F9/28—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
-
- 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
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/02—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of metals or alloys
Definitions
- R denotes an arbitrary aliphatic residue, R, a lower alkyl residue, and R an, optionally substituted, aryl and particularly phenyl residue, or a higher alkyl or cycloalkyl residue with 6 or more C- atoms.
- aliphatic residues refers to saturated as Well as unsaturated residues which may optionally also be further substituted, e.g. by halogen atoms, aryl residues (particularly phenyl residues), and the like.
- cycloalkyl or higher aliphatic alkyl esters is intended to refer to compounds wherein the cycloalkylor higher alkyl-residues contain 6 or more C-atoms.
- reaction is preferably carried out in inert solvents, e.g. alcohol, acetone, benzene, toluene, and sometimes even in water, whereupon the reaction products according to the invention are usually obtained with good yield and purity.
- inert solvents e.g. alcohol, acetone, benzene, toluene, and sometimes even in water
- the new compounds of the present invention very eflfectively kill insects like flies, mites, aphids, etc. They distinguish themselves especially by a good contact-insecticidal activity and at the same time by an activity on eating insects such as caterpillars.
- the compounds may be used in the same manner as other known phosphoric acid insecticides, i.e. in a concentration from about 0.00001% to about 1%, diluted or extended with suitable solid or liquid carriers or diluents.
- solid carriers examples include talc, chalk, bentonite, clay and the like, as liquid carriers there may be mentioned water (if necessary with commercial emulsifiers), alcohols, especially lower alcohols such as methanol or ethanol, ketones, especially lower ketones such as acetone or methyl ethyl ketone, liquid hydrocarbons and the like.
- alcohols especially lower alcohols such as methanol or ethanol
- ketones especially lower ketones such as acetone or methyl ethyl ketone
- liquid hydrocarbons and the like examples of such solid carriers.
- the new com- 3,361,855 Patented Jan. 2, 1968 pounds may furthermore be used in combination with each other or with known insecticides, fertilizers etc.
- esters of the following formulae As an example for the special utility of the inventive compounds the esters of the following formulae:
- Aphids were 40% killed with 0.001% solutions.
- EXAMPLE 1 28 g. (0.25 mol) of thiophenol are dissolved in 50 ml. of methanol. To this is added a solution of sodium methoxide which contains 0.25 mol of dissolved sodium. It is warmed to 60 C. for a short while, and is then cooled to 30 C. 37 g. of methyl-thionophosphonic acid-O-methyl ester-chloride (B.P. 50 C./ 12 mm. Hg) are then added dropwise at 30 C., and it is stirred at 30 C. for another hour. Thereafter, the reaction product is added to 300 ml. of ice water, and the separated oil is taken up in 300 ml. of benzene.
- sodium methoxide which contains 0.25 mol of dissolved sodium. It is warmed to 60 C. for a short while, and is then cooled to 30 C.
- 37 g. of methyl-thionophosphonic acid-O-methyl ester-chloride B.P. 50
- Flies are completely killed with 0.001% solutions. Aphids are 100% killed with solutions of 0.01%.
- Mosquito larvae are completely killed with 0.0001% solutions.
- Caterpillars are completely killed with 0.1% solutions.
- Flies are completely killed with 0.0001% solutions.
- Mosquito larvae are killed with 0.000001% solutions. r
- Spider mites are completely killed with 0.001% solutions, .Aphids are 40% killed with solutions of 0.001%.
- Mosquito larvae are 100% killed with 0.0001% solutions
- the following compounds can be obtained by a similar eggs of the red spider.
- Mosquito larvae are 90% killed with 0.000001% solutions.
- Il/ (ll-CHr-P Aphids are completely killed with 0.01% solutions. Caterpillars are 100% killed with 0.1% solutions.
- EXAMPLE 7 28 g. (0.25 mol) of thiophenol are dissolved in 100 ml. of anhydrous ethyl alcohol. A solution of sodium ethoxide containing 0.25 mol of dissolved sodium is added to it. 57 g. of cyclohexyl-thionophosphonic acid-O-ethyl esterchloride (B.P. 63 C./0.01 mm. Hg) are thereafter added at 35 C. for another hour, and the reaction product is then added to 400 ml. of water. The separated oil is taken up in 300 ml. of benzene, and worked up by the usual method. In this way, 56 g. of the novel ester are obtained as a pale yellow oil insoluble in water. Yield 75% of the theoretical.
- EXAMPLE 8 O CzHs 39 g. (0.25 mol) of p-chloro-thiophenol are dissolved in 120 ml. of anhydrous ethyl alcohol. A solution of sodium ethoxide containing 0.25 mol of dissolved sodium is added at 30 C. 51 g. of isobutenyl-thiophosphonic acid-O-ethyl ester-chloride (B.P. 50 C./0.01 mm. Hg) are thereafter added dropwise at 30 C. whilst stirring Well. It is maintained at 30 C. for an hour, and the reaction product is then added to 300 ml. of ice water. The separated oil is taken up in 300 ml.
- Spider mites are 80% killed with 0.001% solutions.
- the compound shows an ovicidal action against the eggs of the red spider.
- EXAMPLE 9 30 g. (0.25 mol) of n-hexyl-mercaptan are dissolved in ml. of anhydrous ethyl alcohol. A solution of sodium ethoxide containing 0.25 mol of dissolved sodium are added dropwise at 30 C. 64 g. of styryl-thionophosphonic acid-O-ethyl ester-chloride (B.P. 97 C./0.01 mm. Hg) are then added at 30 C. It is stirred for another hour, and is then worked up by the usual method. Thus, 65 g.
- R is methyl, ethyl, chloro-alkyl having up to712 carbon atoms, phenylalkyl having up to 12 carbon atoms or cyclo-hexyl; R is lower alkyl having up to 4 carbon atoms; and R is chlorophenyl.
- R is alkyl having up to 12 car-hon atoms
- R is lower alkyl having up to 4 carbon atoms
- R is chlorophenyl
- R is lower alkyl
- composition of matter O-methyl-S-phenylethylphosphonodithioate.
- composition of matter O-ethyl-S-phenylmethylphosphonodithioate.
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF30537A DE1138049B (de) | 1960-02-13 | 1960-02-13 | Verfahren zur Herstellung von Dithiophosphonsaeureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3361855A true US3361855A (en) | 1968-01-02 |
Family
ID=7093805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US88026A Expired - Lifetime US3361855A (en) | 1960-02-13 | 1961-02-09 | Dithiophosphonic acid esters |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3361855A (de) |
| BE (1) | BE600019A (de) |
| CH (1) | CH388936A (de) |
| DE (1) | DE1138049B (de) |
| GB (1) | GB939946A (de) |
| NL (1) | NL261138A (de) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3442985A (en) * | 1965-10-13 | 1969-05-06 | Stauffer Chemical Co | O-lower alkyl-s-anisyl chloromethylphosphonodithioates |
| US3523999A (en) * | 1965-10-13 | 1970-08-11 | Stauffer Chemical Co | Methods for controlling insects and mites with anisyl chloromethylphosphonodithioates |
| US3881002A (en) * | 1972-06-02 | 1975-04-29 | Monsanto Co | Insecticidal O-phenyl S-aryl alkylphosphonodithioates |
| US4190652A (en) * | 1977-04-02 | 1980-02-26 | Bayer Aktiengesellschaft | Combating pests with O-phenyl-thionothiolalkanephosphonic acid esters |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3205254A (en) * | 1962-02-13 | 1965-09-07 | Stauffer Chemical Co | S-aromatic esters of chloromethyl-phosphonodithioic acids |
| GB1052991A (de) * | 1963-07-02 | |||
| IT1109280B (it) * | 1977-11-11 | 1985-12-16 | Pan Britannica Ind Ltd | Preparato insetticida e procedimento per la sua preparazione |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2910402A (en) * | 1958-02-21 | 1959-10-27 | Du Pont | Compositions and methods for destroying insects |
| US2967884A (en) * | 1958-04-01 | 1961-01-10 | Union Carbide Corp | Preparation of acrylic acid esters |
| US2988474A (en) * | 1960-07-28 | 1961-06-13 | Stauffer Chemical Co | Novel insecticides, acaricides and nematocides |
| US3029270A (en) * | 1959-02-04 | 1962-04-10 | Bayer Ag | Phosphonic acid esters and process for their production |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1071701B (de) * | 1959-12-24 | Farbenfabriken Bayer Aktiengesellschaft, Leverkusen-Bayerwerk | Verfahren zur Herstellung von neuen Dithiophosphonsäureestiern | |
| DE1051851B (de) * | 1957-06-05 | 1959-03-05 | Bayer Ag | Verfahren zur Herstellung von ª‰-Alkoxyvinyldithiophosphonsaeureestern |
| DE1063166B (de) * | 1958-03-26 | 1959-08-13 | Bayer Ag | Verfahren zur Herstellung von beta-Alkylmercapto-vinyldithiophosphonsaeureestern |
| DE1053503B (de) * | 1957-11-02 | 1959-03-26 | Bayer Ag | Verfahren zur Herstellung von schwefelhaltigen Phosphonsaeureestern |
-
0
- NL NL261138D patent/NL261138A/xx unknown
-
1960
- 1960-02-13 DE DEF30537A patent/DE1138049B/de active Pending
-
1961
- 1961-02-06 CH CH136061A patent/CH388936A/de unknown
- 1961-02-09 BE BE600019A patent/BE600019A/fr unknown
- 1961-02-09 US US88026A patent/US3361855A/en not_active Expired - Lifetime
- 1961-02-10 GB GB5131/61A patent/GB939946A/en not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2910402A (en) * | 1958-02-21 | 1959-10-27 | Du Pont | Compositions and methods for destroying insects |
| US2967884A (en) * | 1958-04-01 | 1961-01-10 | Union Carbide Corp | Preparation of acrylic acid esters |
| US3029270A (en) * | 1959-02-04 | 1962-04-10 | Bayer Ag | Phosphonic acid esters and process for their production |
| US2988474A (en) * | 1960-07-28 | 1961-06-13 | Stauffer Chemical Co | Novel insecticides, acaricides and nematocides |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3442985A (en) * | 1965-10-13 | 1969-05-06 | Stauffer Chemical Co | O-lower alkyl-s-anisyl chloromethylphosphonodithioates |
| US3523999A (en) * | 1965-10-13 | 1970-08-11 | Stauffer Chemical Co | Methods for controlling insects and mites with anisyl chloromethylphosphonodithioates |
| US3881002A (en) * | 1972-06-02 | 1975-04-29 | Monsanto Co | Insecticidal O-phenyl S-aryl alkylphosphonodithioates |
| US4190652A (en) * | 1977-04-02 | 1980-02-26 | Bayer Aktiengesellschaft | Combating pests with O-phenyl-thionothiolalkanephosphonic acid esters |
Also Published As
| Publication number | Publication date |
|---|---|
| BE600019A (fr) | 1961-05-29 |
| DE1138049B (de) | 1962-10-18 |
| CH388936A (de) | 1965-03-15 |
| NL261138A (de) | |
| GB939946A (en) | 1963-10-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2891059A (en) | Thiophosphoric acid esters and their production | |
| US2992265A (en) | Phenyl phosphonic acid esters | |
| US3361855A (en) | Dithiophosphonic acid esters | |
| US3205231A (en) | Phosphoric, phosphonic, thionophosphoric or thionophosphinic acid esters | |
| US3056825A (en) | Thiophosphoric acid esters and a process for their production | |
| US3014943A (en) | Phosphonic acid esters | |
| US3092649A (en) | Thiophosphoric acid esters and process for their production | |
| US2910501A (en) | Thiophosphoric acid esters and process for their manufacture | |
| US3294874A (en) | Omicron-alkyl-omicron-cycloalkyl-s-alkylthiolphosphoric acid esters | |
| US3253061A (en) | Thionophosphonic acid esters and processes for their production | |
| US3248412A (en) | Thiophosphonic acid esters | |
| US3150162A (en) | Thiophosphonic acid esters | |
| US3164623A (en) | O-cyanophenyl esters of alkylphosphonic, alkylthiophosphonic, dialkylphosphinic, anddialkylthiophosphinic acids | |
| US3021351A (en) | Phosphorus derivatives and process for their production | |
| US3151146A (en) | Phosphonic and phosphinic acid esters of alpha- and beta-naphthols and processes for heir production | |
| US3322864A (en) | Thionophosphoric acid esters | |
| US3644598A (en) | 1 - alkoxy(-alkenyloxy -phenoxy) - 1-thiono-3-chloro(3-alkyl)phospholines | |
| US3013047A (en) | Phosphorus-containing derivatives of benzylmercaptan and process for their production | |
| US3060217A (en) | Thiophosphoric acid esters | |
| US3053847A (en) | Phosphorus compounds and processes for their production | |
| US2983748A (en) | Thionophosphonic acid esters | |
| US3171853A (en) | S-benzylthiomethyl neutral esters of thiophosphorus pentavalent acids | |
| US3094550A (en) | Thio- and dithio-phosphorus and alkyl esters and process for the production thereof | |
| US3076012A (en) | Phosphoric acid esters and processes for their production | |
| US3029248A (en) | Certain phosphorus esters of 5 hydroxy-2, 1, 3-benzothiadiazole |