GB922781A - Organic thiophosphorus acid derivatives - Google Patents
Organic thiophosphorus acid derivativesInfo
- Publication number
- GB922781A GB922781A GB2681/61A GB268161A GB922781A GB 922781 A GB922781 A GB 922781A GB 2681/61 A GB2681/61 A GB 2681/61A GB 268161 A GB268161 A GB 268161A GB 922781 A GB922781 A GB 922781A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- radical
- formula
- compounds
- alkyl radical
- 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 alkyl radical Chemical class 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000001875 compounds 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000005840 aryl radicals Chemical class 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 150000001733 carboxylic acid esters Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 239000002917 insecticide Substances 0.000 abstract 2
- 150000002825 nitriles Chemical group 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen 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
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 239000000417 fungicide Substances 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000002903 organophosphorus compounds Chemical class 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 150000002989 phenols 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
- 150000003018 phosphorus compounds Chemical class 0.000 abstract 1
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000001174 sulfone group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
- C22B9/00—General processes of refining or remelting of metals; Apparatus for electroslag or arc remelting of metals
- C22B9/16—Remelting metals
- C22B9/22—Remelting metals with heating by wave energy or particle radiation
- C22B9/228—Remelting metals with heating by wave energy or particle radiation by particle radiation, e.g. electron beams
-
- 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
-
- 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
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
-
- 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
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3258—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3264—Esters with hydroxyalkyl compounds
-
- 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
-
- 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)]
- C07F9/44—Amides thereof
- C07F9/4434—Amides thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4438—Ester 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)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Toxicology (AREA)
- Physics & Mathematics (AREA)
- Plasma & Fusion (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises phosphorus compounds of formula <FORM:0922781/IV(a)/1> where R stands for an alkyl radical or for an aryl radical which may be substituted by a halogen atom or an alkyl radical, R1 and R11 are hydrogen or alkyl, R2 and R3 are alkyl, cycloalkyl, alkoxy or phenyl, X is a nitrile, carboxylic ester or carboxylic amide radical, Y is oxygen or sulphur, and n is 0, 1 or 2. They may be obtained by reacting a compound of formula <FORM:0922781/IV(a)/2> with a salt of <FORM:0922781/IV(a)/3> and if desired oxidising the product to the sulphone or sulphoxide; alternatively the oxidation may be effected first. The products are insecticides (see Group VI). Compounds of formula <FORM:0922781/IV(a)/4> are prepared by reacting <FORM:0922781/IV(a)/5> with RS-Hal. Examples prepare compounds in which: X = COOCH3, R11 = CH3 and R = CH3, C2H5 and p-ClC6H4; X = COOC2H5, R11 = CH3 and R = C2H5; X = COOC2H5, R11 = H and R = CH3 and C2H5; X = CN, R11 = H and R = CH3 and C2H5; X = CONH2, R11 = H and R = CH3; (R1 is H in all cases).ALSO:Insecticidal compositions comprise organophosphorus compounds of formula <FORM:0922781/VI/1> where R stands for an alkyl radical or for an aryl radical which may be substituted by a halogen atom or an alkyl radical, R1 and R11 are hydrogen or alkyl, R2 and R3 are alkyl, cycloalkyl, alkoxy or phenyl, X is a nitrile, carboxylic ester or carboxylic amide radical, Y is oxygen or sulphur, and n is 0, 1 or 2, together with a carrier. (For preparation see Group IV (b)). Other insecticides and/or fungicides may be present. Emulsifiers e.g. polyglycollised phenols such as benzyl hydroxy diphenyl polyglycol ether and auxiliary solvents such as acetone may be present.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF30370A DE1116657B (en) | 1960-01-22 | 1960-01-22 | Process for the preparation of derivatives of the thioic acids of phosphorus |
| DEF33812A DE1174756B (en) | 1960-01-22 | 1961-04-29 | Process for the production of thiol or thionothiolphosphorus, -phosphonic or -phosphinic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB922781A true GB922781A (en) | 1963-04-03 |
Family
ID=25974562
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2681/61A Expired GB922781A (en) | 1960-01-22 | 1961-01-23 | Organic thiophosphorus acid derivatives |
| GB15843/62A Expired GB940537A (en) | 1960-01-22 | 1962-04-25 | Organic thiophosphoric acid derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB15843/62A Expired GB940537A (en) | 1960-01-22 | 1962-04-25 | Organic thiophosphoric acid derivatives |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE599323A (en) |
| BR (2) | BR6126059D0 (en) |
| CH (1) | CH398560A (en) |
| DE (1) | DE1174756B (en) |
| FR (1) | FR1280889A (en) |
| GB (2) | GB922781A (en) |
| NL (5) | NL260334A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL282213A (en) * | 1961-08-18 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT195445B (en) * | 1955-03-25 | 1958-02-10 | Montedison Spa | Process for the preparation of new dialkyldithiophosphoric acid derivatives |
-
1961
- 1961-01-17 CH CH49661A patent/CH398560A/en unknown
- 1961-01-20 NL NL260334D patent/NL260334A/nl unknown
- 1961-01-21 FR FR850396A patent/FR1280889A/en not_active Expired
- 1961-01-23 GB GB2681/61A patent/GB922781A/en not_active Expired
- 1961-01-23 BR BR126059/61A patent/BR6126059D0/en unknown
- 1961-01-30 BE BE599323A patent/BE599323A/en unknown
- 1961-04-29 DE DEF33812A patent/DE1174756B/en active Pending
-
1962
- 1962-04-25 GB GB15843/62A patent/GB940537A/en not_active Expired
- 1962-04-27 NL NL277807D patent/NL277807A/nl unknown
- 1962-04-27 BR BR138537/62A patent/BR6238537D0/en unknown
- 1962-05-30 NL NL279139A patent/NL133767C/nl active
- 1962-05-30 NL NL279139D patent/NL279139A/nl unknown
-
1964
- 1964-04-27 NL NL260334A patent/NL133335C/nl active
Also Published As
| Publication number | Publication date |
|---|---|
| NL133335C (en) | 1971-12-17 |
| NL260334A (en) | 1964-04-27 |
| NL133767C (en) | 1972-02-16 |
| BR6238537D0 (en) | 1973-05-10 |
| BE599323A (en) | 1961-02-12 |
| CH398560A (en) | 1966-03-15 |
| DE1174756B (en) | 1964-07-30 |
| BR6126059D0 (en) | 1973-05-31 |
| FR1280889A (en) | 1962-01-08 |
| NL279139A (en) | 1964-11-25 |
| GB940537A (en) | 1963-10-30 |
| NL277807A (en) | 1964-11-10 |
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