GB834392A - Phosphorous acid esters - Google Patents
Phosphorous acid estersInfo
- Publication number
- GB834392A GB834392A GB2157658A GB2157658A GB834392A GB 834392 A GB834392 A GB 834392A GB 2157658 A GB2157658 A GB 2157658A GB 2157658 A GB2157658 A GB 2157658A GB 834392 A GB834392 A GB 834392A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oc2h5
- radical
- phosphorous acid
- alkyl
- substituted
- 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
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 title abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- -1 phosphorous acid ester Chemical class 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 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
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 150000003335 secondary amines Chemical class 0.000 abstract 2
- 125000000101 thioether group Chemical group 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 239000000969 carrier Substances 0.000 abstract 1
- 150000003841 chloride salts Chemical class 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000007865 diluting Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 230000007717 exclusion Effects 0.000 abstract 1
- 239000003337 fertilizer Substances 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/201—Esters of thiophosphorus acids
- C07F9/2015—Esters of thiophosphorus 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
- C07F9/06—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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/201—Esters of thiophosphorus acids
-
- 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
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2408—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyalkyl 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises phosphorous acid esters of the general formula <FORM:0834392/IV (b)/1> wherein R1 is C1-C4 alkyl, X is an alkyl radical substituted by aliphatic or aromatic thioether groups and Y is either -OR1 or the radical of a secondary amine. X may be the radical R2-S-Alk wherein R2 is a C1-C4 alkyl radical or a phenyl radical and Alk is an alkylene radical containing up to 4 carbon atoms and Y may be the radical -NR3R4 wherein R3 and R4 are p hydrocarbon radicals which together contain a total of 6 carbon atoms or wherein NR3R4 forms a heterocyclic radical. They may be obtained by reacting appropriate O,O - dialkyl phosphorous acid monohalides, e.g. monochlorides, or appropriate substituted amino-O-alkyl-phosphorous acid monohalides, e.g. chlorides with salts, e.g. the sodium salt, of appropriately substituted mercaptans (XSH). The reaction is preferably carried out in an inert solvent, e.g. benzene, toluene, or ether, and at an elevated temperature, e.g. 30 DEG -70 DEG C. but with the exclusion of atmospheric oxygen. The following are typical of the products specified: C2H5SCH2CH2SP (OC2H5)2, C6H5SCH2CH2SP(OC2H5)2, C2H5 (or C6H5)SCH(CH3)CH2SP (OC2H5)2, p.Cl (or CH3) C6H4SCH2CH2SP(OC2H5)2, C2H5SCH2 CH2SP(OC3H7)2, C2H5SCH2CH2SP(OC2H5)N (CH3)2, CH3 (or C6H5) SCH2CH2SP(OC2H5)N (C2H5)2, <FORM:0834392/IV (b)/2> <FORM:0834392/IV (b)/3> C2H5SCH2SP(OC2H5)2 C2H5S.CH(CH3)SP(OC2 H5), and C2H5SCH2SP(OC2H5)N N(C2H5)2. The products have insecticidal properties (see Group VI).ALSO:An insecticidal composition comprises a phosphorous acid ester of the formula X.S.P(OR1)Y, wherein R1 is a C1-C4 alkyl radical, X is an alkyl radical substituted by aliphatic or aromatic thioether groups and Y is either OR1 or the radical of a secondary amine (see Group IV (b)) and a solid or liquid diluent or carrier. Specified carriers are talc, chalk, bentonite, clay, water, alcohols, ketones, and liquid hydrocarbons. The phosphorous acid esters may be used in combination with each other or with one or more known insecticides and/or fertilizers. Suitable compositions are obtained by mixing the compounds C2H5SCH2CH2SP(OC2H5)2 and C2H5SCH2CH2SP(OC2H5)N (CH3)2 respectively with acetone, adding benzyl hydroxy diphenyl ether as emulsifier and then diluting with water.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0023434 | 1957-07-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB834392A true GB834392A (en) | 1960-05-04 |
Family
ID=7090838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2157658A Expired GB834392A (en) | 1957-07-10 | 1958-07-04 | Phosphorous acid esters |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT207385B (en) |
| BE (1) | BE569276A (en) |
| CH (1) | CH385193A (en) |
| DE (1) | DE1050331B (en) |
| FR (1) | FR1199166A (en) |
| GB (1) | GB834392A (en) |
| IT (1) | IT593773A (en) |
| NL (1) | NL106875C (en) |
| NO (1) | NO96166A (en) |
-
0
- DE DENDAT1050331D patent/DE1050331B/en active Pending
- NL NL106875D patent/NL106875C/xx active
- IT IT593773D patent/IT593773A/it unknown
- NO NO96166D patent/NO96166A/no unknown
- BE BE569276D patent/BE569276A/xx unknown
-
1958
- 1958-06-30 CH CH6123458A patent/CH385193A/en unknown
- 1958-07-02 AT AT466458A patent/AT207385B/en active
- 1958-07-04 GB GB2157658A patent/GB834392A/en not_active Expired
- 1958-07-07 FR FR1199166D patent/FR1199166A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT593773A (en) | |
| CH385193A (en) | 1964-12-15 |
| AT207385B (en) | 1960-01-25 |
| FR1199166A (en) | 1959-12-11 |
| NO96166A (en) | |
| NL106875C (en) | |
| BE569276A (en) | |
| DE1050331B (en) | 1959-02-12 |
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