GB1034185A - Improvements in or relating to thiophosphonic acid derivatives - Google Patents
Improvements in or relating to thiophosphonic acid derivativesInfo
- Publication number
- GB1034185A GB1034185A GB4033/63A GB403363A GB1034185A GB 1034185 A GB1034185 A GB 1034185A GB 4033/63 A GB4033/63 A GB 4033/63A GB 403363 A GB403363 A GB 403363A GB 1034185 A GB1034185 A GB 1034185A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- substituents
- compound
- clch2
- general 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 1
- -1 naphthyl radical Chemical class 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- ZOAMZFNAPHWBEN-UHFFFAOYSA-N 2-$l^{1}-oxidanylpropane Chemical compound CC(C)[O] ZOAMZFNAPHWBEN-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 241000607479 Yersinia pestis Species 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000006185 dispersion Substances 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 239000011574 phosphorus Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 238000007865 diluting Methods 0.000 abstract 1
- 239000000428 dust Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- 231100000208 phytotoxic Toxicity 0.000 abstract 1
- 230000000885 phytotoxic effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004563 wettable powder Substances 0.000 abstract 1
- 239000000080 wetting agent Substances 0.000 abstract 1
- 239000008096 xylene 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
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- 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
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds 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
- C07F9/28—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)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises compounds of the general formula (ClCH2)(Y).P.(S)SZ wherein Y is a normal- or iso-propoxy radical and Z is a naphthyl radical or a substituted aryl radical or substituted alkaryl radical said substituents being halo- (e.g. Cl, Br or F) and/or nitro-substituents. They may be obtained by reacting a compound of the general formula (ClCH2)(Y)P(S)Hal wherein Y is as defined above and Hal is a halogen atom with a compound ZSH wherein Z is as defined above in the presence of a hydrogen halide acceptor, e.g. triethylamine, while maintaining the reaction temperature at between 0 DEG and 100 DEG C., preferably between 30 DEG and 65 DEG C. The reaction is preferably carried out in an organic solvent, e.g. benzene, dioxane, toluene or xylene. Several examples are given and the products are useful for controlling pests and undesired plants (see Division A5).ALSO:Pests or undesired plants are controlled by contacting them with a pesticidal or phytotoxic amount respectively of at least one phosphorus compound having the general formula:- (ClCH2)(Y)P(S)SZ wherein Y is a normal or iso-propoxy radical and Z is a naphthyl radical or a substituted aryl or substituted alkaryl radical, said substituents being halogen (e.g. Cl, Br or F) and/or nitro substituents (see Division C2). The phosphorus compound may be used above or in the form of an aqueous or non-aqueous solution, aqueous dispersion, wettable powder, vapour or dust. The aqueous dispersion may be obtained by dissolving the active compound in acetone and diluting with water containing wetting agents. When used as herbicides the active compound may be applied to the coil after planting but before emergence of the plants.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17289062A | 1962-02-13 | 1962-02-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1034185A true GB1034185A (en) | 1966-06-29 |
Family
ID=22629624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4033/63A Expired GB1034185A (en) | 1962-02-13 | 1963-01-31 | Improvements in or relating to thiophosphonic acid derivatives |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE628296A (en) |
| CH (1) | CH465320A (en) |
| DE (1) | DE1184759B (en) |
| FR (1) | FR1348127A (en) |
| GB (1) | GB1034185A (en) |
| NL (2) | NL139651B (en) |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2714100A (en) * | 1952-08-05 | 1955-07-26 | Victor Chemical Works | Diallyl monochloromethanephosphonate and polymers |
| US2900405A (en) * | 1953-05-29 | 1959-08-18 | Eastman Kodak Co | Halomethanephosphonates |
| US2922810A (en) * | 1953-07-13 | 1960-01-26 | Victor Chemical Works | Chloromethanephosphonic acid esters |
| US2841604A (en) * | 1954-08-23 | 1958-07-01 | Victor Chemical Works | Dialkyl monochloromethanephosphonate esters containing from 3 to 10 carbon atoms in the hydrocarbon radicals |
| US2960522A (en) * | 1954-10-07 | 1960-11-15 | Victor Chemical Works | Dicresyl monochloromethane-phosphonate |
| US2863903A (en) * | 1954-10-07 | 1958-12-09 | Victor Chemical Works | Alkyl aryl monochloromethane-phosphonate esters |
| US2927014A (en) * | 1957-02-14 | 1960-03-01 | Virginia Carolina Chem Corp | Method for killing plants |
| US2910402A (en) * | 1958-02-21 | 1959-10-27 | Du Pont | Compositions and methods for destroying insects |
| US2988565A (en) * | 1958-11-14 | 1961-06-13 | Victor Chemical Works | O-ethyl-o-ethylmercaptoethyl chloromethylthionophosphonate |
| FR1280984A (en) * | 1960-02-13 | 1962-01-08 | Bayer Ag | Dithiophosphonic esters and process for their preparation |
| NL267577A (en) * | 1960-07-28 | |||
| FR1266440A (en) * | 1960-09-03 | 1961-07-07 | Stauffer Chemical Co | New thio-phosphonates, active in particular as acaricides and insecticides |
-
0
- NL NL288842D patent/NL288842A/xx unknown
- BE BE628296D patent/BE628296A/xx unknown
-
1963
- 1963-01-31 GB GB4033/63A patent/GB1034185A/en not_active Expired
- 1963-02-11 CH CH167263A patent/CH465320A/en unknown
- 1963-02-12 NL NL63288842A patent/NL139651B/en unknown
- 1963-02-12 DE DEST20283A patent/DE1184759B/en active Pending
- 1963-02-13 FR FR924589A patent/FR1348127A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL288842A (en) | |
| FR1348127A (en) | 1964-01-04 |
| BE628296A (en) | |
| DE1184759B (en) | 1965-01-07 |
| CH465320A (en) | 1968-11-15 |
| NL139651B (en) | 1973-09-17 |
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