GB1016670A - Phosphorus acid esters and their use as pesticides - Google Patents
Phosphorus acid esters and their use as pesticidesInfo
- Publication number
- GB1016670A GB1016670A GB49413/64A GB4941364A GB1016670A GB 1016670 A GB1016670 A GB 1016670A GB 49413/64 A GB49413/64 A GB 49413/64A GB 4941364 A GB4941364 A GB 4941364A GB 1016670 A GB1016670 A GB 1016670A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radicals
- straight
- chain alkyl
- different
- formula
- 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
- 239000002253 acid Substances 0.000 title abstract 3
- 239000000575 pesticide Substances 0.000 title abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title 1
- 150000002148 esters Chemical class 0.000 title 1
- 229910052698 phosphorus Inorganic materials 0.000 title 1
- 239000011574 phosphorus Substances 0.000 title 1
- -1 alkoxy radicals Chemical class 0.000 abstract 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000003085 diluting agent Substances 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 239000000843 powder Substances 0.000 abstract 3
- 239000007787 solid Substances 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 239000011230 binding agent Substances 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract 2
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 239000002969 artificial stone Substances 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 238000010410 dusting Methods 0.000 abstract 1
- 239000004495 emulsifiable concentrate Substances 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 229920005610 lignin Polymers 0.000 abstract 1
- 235000019359 magnesium stearate Nutrition 0.000 abstract 1
- 235000012054 meals Nutrition 0.000 abstract 1
- 229920000609 methyl cellulose Polymers 0.000 abstract 1
- 239000001923 methylcellulose Substances 0.000 abstract 1
- 235000010981 methylcellulose Nutrition 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- 150000004760 silicates Chemical class 0.000 abstract 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 abstract 1
- 235000012239 silicon dioxide Nutrition 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007921 spray Substances 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- 239000002699 waste material Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3258—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3282—Esters with hydroxyaryl 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
- A01N57/06—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 aromatic 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl 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
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl 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
- C07F9/28—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
- C07F9/4084—Esters with hydroxyaryl compounds
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention comprises compounds of the formula <FORM:1016670/C2/1> wherein R and R1, which may be the same or different, are straight or branched chain alkyl or alkoxy radicals or unsubstituted or substituted aryl radicals, X is an oxygen or sulphur atom and Y and Y1, which may be the same or different, are hydrogen or halogen atoms or straight or branched chain alkyl radicals. They are prepared by reacting an ester halide of the general formula <FORM:1016670/C2/2> in which Hal is a halogen atom with a 4, 41-dihydroxy-diphenyl disulphide of the formula <FORM:1016670/C2/3> The reaction is preferably carried out in the presence of inert organic solvents and acid-binding agents at a temperature of 25 DEG C. to 100 DEG C. Suitable inert organic solvents are lower aliphatic ketones and nitriles and hydrocarbons preferably unsubstituted mononuclear aryl hydrocarbons. Preferred acid - binding agents are alkali metal carbonates and alcoholates and secondary or tertiary nitrogen bases. The compounds can be used as pesticides in admixture with a solid or liquid diluent or carrier (see Division A5).ALSO:A pesticidal composition comprises a solid or liquid diluent or carrier and an active compound of the formula: <FORM:1016670/A5-A6/1> wherein R and R1, which may be the same or different, are straight or branded chain alkyl or alkoxy radicals or unsubstituted or substituted aryl radicals, X is an oxygen or sulphur atom and Y and Y1, which may be the same or different, are hydrogen or halogen atoms or straight or branched chain alkyl radicals (see Division C2). Suitable diluents or carriers are solvents such as optionally chlorinated aromatic hydrocarbons, paraffins, alcohols, amines, dimethyl formamide, water and, especially methylene chloride, finely divided. Solids such as natural and synthetic stone meals or powders e.g. kaotin, alumina, chalk, talc and highly dispersed silicic acid and silicates, emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, alkyl and aryl sulphonates, magnesium stearate and sodium oleate and dispersing agents such as lignin sulphite waste liquors and methyl cellulose. The compositions may be in the form of emulsifiable concentrates, spray powders, pastes, soluble powders, dusting agents or granulates.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF41465A DE1197878B (en) | 1963-12-04 | 1963-12-04 | Process for the production of phosphorus, phosphonic, phosphine or thionophosphorus, -phosphonic, -phosphinic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1016670A true GB1016670A (en) | 1966-01-12 |
Family
ID=7098680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB49413/64A Expired GB1016670A (en) | 1963-12-04 | 1964-12-04 | Phosphorus acid esters and their use as pesticides |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE656531A (en) |
| DE (1) | DE1197878B (en) |
| ES (1) | ES306759A1 (en) |
| GB (1) | GB1016670A (en) |
| NL (1) | NL6414133A (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1329773A (en) * | 1961-06-06 | 1963-06-14 | Bayer Ag | Process for the preparation of (thio) -phosphor-, -phosphon- and -phosphinic acid esters |
-
1963
- 1963-12-04 DE DEF41465A patent/DE1197878B/en active Pending
-
1964
- 1964-12-02 BE BE656531D patent/BE656531A/xx unknown
- 1964-12-04 NL NL6414133A patent/NL6414133A/xx unknown
- 1964-12-04 ES ES0306759A patent/ES306759A1/en not_active Expired
- 1964-12-04 GB GB49413/64A patent/GB1016670A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL6414133A (en) | 1965-06-07 |
| BE656531A (en) | 1965-06-02 |
| DE1197878B (en) | 1965-08-05 |
| ES306759A1 (en) | 1965-04-01 |
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