GB909325A - Aromatic sulphenyl-phosphorus thioates and process for their production - Google Patents
Aromatic sulphenyl-phosphorus thioates and process for their productionInfo
- Publication number
- GB909325A GB909325A GB3588160A GB3588160A GB909325A GB 909325 A GB909325 A GB 909325A GB 3588160 A GB3588160 A GB 3588160A GB 3588160 A GB3588160 A GB 3588160A GB 909325 A GB909325 A GB 909325A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chlorophenyl
- alkoxy group
- substituted aryl
- alkyl
- halogen
- 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
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 title abstract 2
- 125000003118 aryl group Chemical group 0.000 title 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 4
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- -1 halogen substituted aryl sulphenic acid chlorides Chemical class 0.000 abstract 2
- 230000000749 insecticidal effect Effects 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- WVTOJNFZIVWNIY-UHFFFAOYSA-N (4-chlorophenyl) thiohypochlorite Chemical compound ClSC1=CC=C(Cl)C=C1 WVTOJNFZIVWNIY-UHFFFAOYSA-N 0.000 abstract 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 abstract 1
- VZXOZSQDJJNBRC-UHFFFAOYSA-N 4-chlorobenzenethiol Chemical compound SC1=CC=C(Cl)C=C1 VZXOZSQDJJNBRC-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001298 alcohols 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 239000003337 fertilizer Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 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
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 150000003009 phosphonic acids Chemical class 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- 150000003016 phosphoric acids Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 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
- C07F9/28—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
- C07F9/409—Compounds containing the structure P(=X)-X-acyl, P(=X) -X-heteroatom, P(=X)-X-CN (X = O, S, Se)
-
- 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
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1654—Compounds containing the structure P(=X)n-X-acyl, P(=X)n-X-heteroatom, P(=X)n-X-CN (X = O, S, Se; n = 0, 1)
- C07F9/1655—Compounds containing the structure P(=X)n-S-(S)x- (X = O, S, Se; n=0,1; x>=1)
-
- 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
- C07F9/4075—Esters with hydroxyalkyl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises sulphenyl phosphorus thioates of the general formula: <FORM:0909325/IV (b)/1> wherein R1 is a C1-C4 alkoxy group or a C1-C4 alkyl group, R2 is a C1-C1 alkoxy group, R3\t is a halogen-substituted aryl radical and X is an oxygen or sulphur atom. They may be obtained by reacting halogen substituted aryl sulphenic acid chlorides with appropriate O,O-dialkyl-thiol- or thionothiol phosphoric acids or with appropriate O-alkyl-thiol or -thionothiol phosphonic acids. The reaction is preferably carried out in the presence of an inert solvent e.g. carbon tetrachloride and is suitably carried out in the absence of an acid binding agent. Several examples are given and the specified products include the following: (C2H5O)2P(X)S.S.R3 wherein X is O or S and R3 is 4-chlorophenyl or 2,4-dichlorophenyl, C2H5P(S)(O sec. butyl)S.S - 2 - bromo-4-chlorophenyl, and (C2H5O)(CH3)P(O)S.S-p-chlorophenyl. The products have insecticidal properties (see Group VI). p-Chlorophenyl sulphenic acid chloride is obtained by the action of chlorine on p-chlorophenylmercaptan in carbon tetrachloride.ALSO:An insecticidal composition comprises a solid or liquid carrier or diluent and a compound of the general formula <FORM:0909325/VI/1> wherein R1 is a C1-C4 alkyl or alkoxy group, R2 is a C1-C4 alkoxy group, R3 is a halogen-substituted aryl radical and X is an oxygen or sulphur atom. 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.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF29652A DE1103324B (en) | 1959-10-20 | 1959-10-20 | Process for the production of sulfenylthiophosphoric acid esters or thiophosphonic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB909325A true GB909325A (en) | 1962-10-31 |
Family
ID=7093406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3588160A Expired GB909325A (en) | 1959-10-20 | 1960-10-19 | Aromatic sulphenyl-phosphorus thioates and process for their production |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE596202A (en) |
| CH (1) | CH387019A (en) |
| DE (1) | DE1103324B (en) |
| GB (1) | GB909325A (en) |
| IT (1) | IT649708A (en) |
| NL (1) | NL257078A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1199762B (en) * | 1961-07-12 | 1965-09-02 | R I A F Societa Azionaria Roma | Process for the preparation of nematocidally active dithiophosphoric acid esters |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR994479A (en) * | 1949-07-10 | 1951-11-16 | S-nitrophenyl-0, 0-dialkylthiolphosphates and process for obtaining them | |
| DE1046062B (en) * | 1957-03-01 | 1958-12-11 | Bayer Ag | Process for the preparation of insecticidally active dialkyl-thionothiolphosphoric acid esters |
-
0
- IT IT649708D patent/IT649708A/it unknown
- BE BE596202D patent/BE596202A/xx unknown
- NL NL257078D patent/NL257078A/xx unknown
-
1959
- 1959-10-20 DE DEF29652A patent/DE1103324B/en active Pending
-
1960
- 1960-10-13 CH CH1152860A patent/CH387019A/en unknown
- 1960-10-19 GB GB3588160A patent/GB909325A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL257078A (en) | |
| CH387019A (en) | 1965-01-31 |
| BE596202A (en) | |
| IT649708A (en) | |
| DE1103324B (en) | 1961-03-30 |
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