GB989014A - Thiophosphonates and compositions containing the same - Google Patents
Thiophosphonates and compositions containing the sameInfo
- Publication number
- GB989014A GB989014A GB797862A GB797862A GB989014A GB 989014 A GB989014 A GB 989014A GB 797862 A GB797862 A GB 797862A GB 797862 A GB797862 A GB 797862A GB 989014 A GB989014 A GB 989014A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- general formula
- methyl
- powdered
- dioxane
- 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
- 239000000203 mixture Substances 0.000 title abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 3
- 239000004094 surface-active agent Substances 0.000 abstract 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 2
- 239000004480 active ingredient Substances 0.000 abstract 2
- -1 alkyl phenol Chemical compound 0.000 abstract 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 230000000749 insecticidal effect Effects 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- 239000008096 xylene Substances 0.000 abstract 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 abstract 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 abstract 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 abstract 1
- 240000007049 Juglans regia Species 0.000 abstract 1
- 235000009496 Juglans regia Nutrition 0.000 abstract 1
- 239000004264 Petrolatum Substances 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 239000000443 aerosol Substances 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000000129 anionic group Chemical group 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 1
- 239000003899 bactericide agent Substances 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 125000002091 cationic group Chemical group 0.000 abstract 1
- 239000012050 conventional carrier Substances 0.000 abstract 1
- 239000007799 cork Substances 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 239000000428 dust Substances 0.000 abstract 1
- 239000000839 emulsion 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
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 abstract 1
- 239000003906 humectant Substances 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 239000003350 kerosene Substances 0.000 abstract 1
- 239000002480 mineral oil Substances 0.000 abstract 1
- 150000002790 naphthalenes Chemical class 0.000 abstract 1
- 230000001069 nematicidal effect Effects 0.000 abstract 1
- 239000005645 nematicide Substances 0.000 abstract 1
- 229940049964 oleate Drugs 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000008188 pellet Substances 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 229940066842 petrolatum Drugs 0.000 abstract 1
- 235000019271 petrolatum Nutrition 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 229940051841 polyoxyethylene ether Drugs 0.000 abstract 1
- 229920000056 polyoxyethylene ether Polymers 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 239000000344 soap Substances 0.000 abstract 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000002904 solvent Chemical class 0.000 abstract 1
- 238000000638 solvent extraction Methods 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 230000009885 systemic effect Effects 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 235000020234 walnut Nutrition 0.000 abstract 1
- 239000002023 wood Substances 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
- C07F9/38—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)
- 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 alkyl alkylthiophosphonates of the general formula <FORM:0989014/C2/1> in which R is a normal C3 or C4 alkyl group and R1 is a methyl or ethyl group. They may be obtained by treating an alkyl alkylthiophosphonyl halide of the general formula <FORM:0989014/C2/2> in which R and R1 are as above defined and Z is a halogen having an atomic number of at least 17 with 4-nitro-phenol in the presence of an acid acceptor, e.g. an alkali metal carbonate or a tertiary amine. An inert organic solvent e.g. acetone, butanone, dioxane, benzene, toluene, or xylene may be present. Preferred reaction temperatures are from 10 DEG C. to 120 DEG C. and the product may be purified by selective solvent extraction or by absorptive agents such as activated carbon or clays. The products have insecticidal properties (see Division A5).ALSO:An insecticidal composition comprises an alkylthiophosphonate of the general formula <FORM:0989014/A5-A6/1> wherein R is a normal C3 or C4 alkyl group and R1 is a methyl or ethyl group (see Division C2) and a carrier and/or water-soluble surfactant. The active ingredient is both a systemic and contact insecticide and the composition may be in the form of a solution, suspension or emulsion in an organic liquid or may be in the form of pellets, granules, powder or dust or in the form of a mixture, e.g. with a fluorochloroalkane, which is suitable as an aerosol. An adhesive, spreading agent, or humectant may also be present. Specified organic liquids are isopropyl ether, acetone, methyl ethyl ketone, dioxane, cyclohexanone, carbon tetrachloride, ethylene dichloride, tetrachloroethane, hexane, heptane, low molecular weight aliphatic hydrocarbons, hydrogenated naphthalenes, solvent naphtha, benzene, toluene, xylene, petroleum fractions (especially kerosene), and mineral oils having an unsulphonatable residue above 80%. The surfactant may be an anionic, cationic or non-ionic surface-active agent, an alkali metal alkylaryl sulphonate, a polyoxyethylene ether of an alkyl phenol or of a mono-higher fatty acid ester of a hexitan (e.g. sorbitan) being preferred. Specified solid carriers include the conventional carriers, volcanic ash, sulphur, powdered cork, powdered wood and powdered walnut shells. The active ingredient may also be dispersed in a semi-solid extending agent, e.g. petrolatum or soap, e.g. sodium stearate, oleate or palmitate. Other pesticides, e.g. nematocides, bactericides or herbicides may also be present.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US92446A US3165441A (en) | 1961-03-01 | 1961-03-01 | Methylphosphonothioate insecticide |
| US9304261A | 1961-03-03 | 1961-03-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB989014A true GB989014A (en) | 1965-04-14 |
Family
ID=26785688
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB797862A Expired GB989014A (en) | 1961-03-01 | 1962-03-01 | Thiophosphonates and compositions containing the same |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB989014A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9398771B2 (en) | 2011-11-23 | 2016-07-26 | Roderick William Phillips | Spray apparatuses, uses of diatomaceous earth, and methods of controlling insect populations |
| US10485351B2 (en) | 2011-05-03 | 2019-11-26 | Roderick William Phillips | Headboard apparatus for holding a decorative cover |
-
1962
- 1962-03-01 GB GB797862A patent/GB989014A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10485351B2 (en) | 2011-05-03 | 2019-11-26 | Roderick William Phillips | Headboard apparatus for holding a decorative cover |
| US11140993B2 (en) | 2011-05-03 | 2021-10-12 | Roderick William Phillips | Headboard apparatus for holding a decorative cover and having diatomaceous earth incorporated therein for pest control |
| US9398771B2 (en) | 2011-11-23 | 2016-07-26 | Roderick William Phillips | Spray apparatuses, uses of diatomaceous earth, and methods of controlling insect populations |
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