GB814587A - New dithiophosphate ester and insecticidal compositions comprising it - Google Patents
New dithiophosphate ester and insecticidal compositions comprising itInfo
- Publication number
- GB814587A GB814587A GB35118/57A GB3511857A GB814587A GB 814587 A GB814587 A GB 814587A GB 35118/57 A GB35118/57 A GB 35118/57A GB 3511857 A GB3511857 A GB 3511857A GB 814587 A GB814587 A GB 814587A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- ester
- reacting
- mixture
- morpholide
- 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
- 150000002148 esters Chemical class 0.000 title abstract 8
- 239000000203 mixture Substances 0.000 title abstract 8
- 230000000749 insecticidal effect Effects 0.000 title abstract 2
- 239000002253 acid Substances 0.000 abstract 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 6
- YMQRPXBBBOXHNZ-UHFFFAOYSA-N 2-chloro-1-morpholin-4-ylethanone Chemical compound ClCC(=O)N1CCOCC1 YMQRPXBBBOXHNZ-UHFFFAOYSA-N 0.000 abstract 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- 239000000839 emulsion Substances 0.000 abstract 3
- 239000005995 Aluminium silicate Substances 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- -1 alkyl phenols Chemical class 0.000 abstract 2
- 235000012211 aluminium silicate Nutrition 0.000 abstract 2
- 239000003995 emulsifying agent Substances 0.000 abstract 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- 239000000454 talc Substances 0.000 abstract 2
- 229910052623 talc Inorganic materials 0.000 abstract 2
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 abstract 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 1
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 239000007900 aqueous suspension Substances 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 239000000440 bentonite Substances 0.000 abstract 1
- 229910000278 bentonite Inorganic materials 0.000 abstract 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 239000000428 dust Substances 0.000 abstract 1
- 238000010410 dusting Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000002480 mineral oil Substances 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- 150000003014 phosphoric acid esters Chemical class 0.000 abstract 1
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 150000005846 sugar alcohols Polymers 0.000 abstract 1
- 230000009885 systemic effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/6533—Six-membered rings
-
- 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
- C07F9/547—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
- C07F9/576—Six-membered rings
- C07F9/59—Hydrogenated pyridine rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises a thiolthionophosphoric acid ester of the formula <FORM:0814587/IV (b)/1> It may be obtained by reacting a salt of O,O-dimethylthiolthionophosphoric acid with chloracetic acid morpholide or by reacting O,O-dimethyl-thiolthionophosphoric acid with chloracetic acid morpholide in the presence of an acid binding agent. Examples are given in which the ester is obtained by (1) reacting the ammonium salt of dimethylthiolthionophosphoric acid with chloracetic acid morpholide in the presence of acetone at 45-50 DEG C. for 5 hours; (2) by refluxing O,O-dimethyl thiolthionophosphoric acid with chloracetic acid morpholide in the presence of anhydrous sodium carbonate and acetone, and (3) by reacting O,O-dimethylthiolthionophosphoric acid with chloracetic acid morpholide in the presence of pyridine and benzene. The product is stated to have good pesticidal properties (see Group VI).ALSO:An insecticidal composition having both contact and systemic action comprises a thiothionophosphoric acid ester of the formula <FORM:0814587/VI/1> (see Group IV (b)) together with a solvent, emulsifier, or powdered water-insoluble inorganic substance. Suitable emulsifiers are liquid polyglycol ethers which are obtained from higher molecular alcohols, mercaptans or alkyl phenols by the addition of ethylene oxide and suitable solvents are mono- or poly-hydric alcohols, aromatic hydrocarbons or mineral oils. Specified solid carriers are talc, kaolin, kieselguhr and p bentonite. The composition is preferably used in the form of an emulsion or dispersion in water containing 0.01 to 0.3 per cent by weight of the thiolthisono phosphoric acid ester but may also be used in the form of a dust by the addition of an adhesive and a suitable solid carrier substance. Examples are given to show the effect of the following compositions as insecticides: (1) an aqueous emulsion of a mixture of the ester with di-isohexylheptylphenyl hexaglycol ether and alcohol; (2) an aqueous emulsion of a mixture of the ester with laurylhexaglycol ether, propylene glycol, and butoxyethoxy-ethanol; (3) a dusting agent made by grinding a mixture of 2 parts by weight of the ester with 98 parts by weight of talc in a ball mill; and (4) an aqueous suspension of a mixture of the ester with tert-dodecylmercaptan undecaglycol ether, powdered silica gel and kaolin.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH814587X | 1956-11-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB814587A true GB814587A (en) | 1959-06-10 |
Family
ID=4538831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35118/57A Expired GB814587A (en) | 1956-11-16 | 1957-11-11 | New dithiophosphate ester and insecticidal compositions comprising it |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE562144A (en) |
| FR (1) | FR1215549A (en) |
| GB (1) | GB814587A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3406179A (en) * | 1966-07-29 | 1968-10-15 | Hercules Inc | 1-(mercaptoacetyl)-2-imidazolidone s-(o, o-dialkylphosphorothioates) |
| US4775666A (en) * | 1985-10-25 | 1988-10-04 | Basf Aktiengesellschaft | Bisthiolphosphate, their use for combatting pests |
-
0
- BE BE562144D patent/BE562144A/xx unknown
-
1957
- 1957-11-11 GB GB35118/57A patent/GB814587A/en not_active Expired
- 1957-11-14 FR FR751591A patent/FR1215549A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3406179A (en) * | 1966-07-29 | 1968-10-15 | Hercules Inc | 1-(mercaptoacetyl)-2-imidazolidone s-(o, o-dialkylphosphorothioates) |
| US4775666A (en) * | 1985-10-25 | 1988-10-04 | Basf Aktiengesellschaft | Bisthiolphosphate, their use for combatting pests |
Also Published As
| Publication number | Publication date |
|---|---|
| BE562144A (en) | |
| FR1215549A (en) | 1960-04-19 |
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