GB867794A - Phosphonic acid esters - Google Patents
Phosphonic acid estersInfo
- Publication number
- GB867794A GB867794A GB20086/58A GB2008658A GB867794A GB 867794 A GB867794 A GB 867794A GB 20086/58 A GB20086/58 A GB 20086/58A GB 2008658 A GB2008658 A GB 2008658A GB 867794 A GB867794 A GB 867794A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- substituted
- radical
- alkyl radical
- phenyl
- 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
- 150000003008 phosphonic acid esters Chemical class 0.000 title abstract 2
- -1 aryl substituted alkyl radical Chemical class 0.000 abstract 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 125000005907 alkyl ester group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- NAKDJXIEBCHXIZ-UHFFFAOYSA-N dihydroxy-phenyl-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(=S)C1=CC=CC=C1 NAKDJXIEBCHXIZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- 239000003995 emulsifying agent Substances 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 230000000749 insecticidal effect Effects 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 abstract 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 abstract 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000003118 aryl group Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 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
- 125000003236 benzoyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 238000007865 diluting Methods 0.000 abstract 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000003337 fertilizer Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 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
- C07F9/4087—Esters with arylalkanols
-
- 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
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4021—Esters of aromatic acids (P-C aromatic linkage)
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 phosphonic acid esters of the formula C6H5P(O)(OR1)(SR2) wherein R1 is alkyl containing 1 to 4 carbon atoms, and R2 is a C8-C20 alkyl radical, an aryl substituted alkyl radical, such as a benzyl radical, which may be substituted in the nucleus by one or more chlorine atoms or by a C1-C6 alkylmercapto radical, a cyano substituted C1-C6 alkyl radical or a benzoyl substtuted C1-C6 alkyl radical. They may be obtained by reacting the corresponding phenyl phosphonic acid alkyl ester halide with an appropriately substituted mercapto compound or by reacting a phenyl thiono-phosphonic acid alkyl ester chloride of the formula C6H5P(S)(OR1)Cl with 2 molecular proportions of an alkali metal hydroxide to give an alkali metal salt of a phenyl thionophosphonic alkyl ester which is then reacted with an appropriate alkyl or substituted alkyl halide whereby the said ester reacts in its tantomeric thiolo form to give the desired product. Examples are given for the production of compounds of the above formula in which R1 is ethyl and R2 is 3,4-dichlorobenzyl, p-chlorobenzyl, benzyl, dodecyl, -CH2CN, -CO-C6H5, and 1-methylcapto-4-methyl phenyl respectively, and in which R1 is CH3 and R2 is benzyl. The products have insecticidal properties (see Group VI). The compound C6H5-P(S)(OC2H5)(OK) used as a starting material is obtained by reacting an acetonitrile solution of phenyl thiono-phosphonic acid ester chloride to which water has been added with an aqueous solution of potassium hydroxide at about 70 DEG C.ALSO:An insecticidal composition comprises one or more esters of the general formula R.P(O)(OR1)(SR2), wherein R is phenyl, R1 is a C1-C4 alkyl radical, and R2 is an alkyl radical containing 8 to 20 carbon atoms, a cyano-substituted C1 to C6 alkyl radical, a benzoyl-substituted C1-C6 alkyl radical, or an aryl substututed alkyl radical, such as a benzyl radical which may be substituted in the nucleus by one or more chloric atoms or by a C1-C6 alkyl-mercapto radical (see Group IV (b)), and a solid or liquid carrier or diluent. Specified carriers or diluents are talc, chalk, bentonite, clay, water (if necessary with an emulsifier), alcohols, ketones and liquid hydrocarbons. Known insecticides and/or fertilizers may also be present. A typical composition is obtained by mixing the compound <FORM:0867794/VI/1> with acetone, adding benzyl hydroxy diphenyl polyglycol ether as emulsifying agent and then diluting with water.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE867794X | 1957-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB867794A true GB867794A (en) | 1961-05-10 |
Family
ID=6802208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20086/58A Expired GB867794A (en) | 1957-06-24 | 1958-06-23 | Phosphonic acid esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB867794A (en) |
-
1958
- 1958-06-23 GB GB20086/58A patent/GB867794A/en not_active Expired
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