GB1017983A - Pesticidal heterocyclic phosphorus acid esters - Google Patents
Pesticidal heterocyclic phosphorus acid estersInfo
- Publication number
- GB1017983A GB1017983A GB278164A GB278164A GB1017983A GB 1017983 A GB1017983 A GB 1017983A GB 278164 A GB278164 A GB 278164A GB 278164 A GB278164 A GB 278164A GB 1017983 A GB1017983 A GB 1017983A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- substituted
- phenyl
- alkenyl
- alkoxy
- 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 abstract 5
- 150000002148 esters Chemical class 0.000 title abstract 5
- 125000000623 heterocyclic group Chemical group 0.000 title abstract 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 title abstract 2
- 239000011574 phosphorus Substances 0.000 title abstract 2
- 230000000361 pesticidal effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 13
- 125000003342 alkenyl group Chemical group 0.000 abstract 6
- -1 nitro-substituted phenyl Chemical group 0.000 abstract 6
- 125000003282 alkyl amino group Chemical group 0.000 abstract 5
- 229910052760 oxygen Inorganic materials 0.000 abstract 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 150000002431 hydrogen Chemical group 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 229910052717 sulfur Inorganic materials 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 239000011230 binding agent Substances 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 125000006323 alkenyl amino group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 239000003995 emulsifying agent Substances 0.000 abstract 2
- 239000002917 insecticide Substances 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 150000003017 phosphorus Chemical class 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- CZWWCTHQXBMHDA-UHFFFAOYSA-N 3h-1,3-thiazol-2-one Chemical class OC1=NC=CS1 CZWWCTHQXBMHDA-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 150000001340 alkali metals 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 239000012141 concentrate Substances 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000003701 inert diluent Substances 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 239000003879 lubricant additive Substances 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 150000003557 thiazoles Chemical class 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
- C10M137/105—Thio derivatives not containing metal
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/12—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond
- C10M137/14—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/047—Thioderivatives not containing metallic elements
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/049—Phosphite
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/061—Metal salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (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)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
The invention comprises esters of phosphorus acids, of formula <FORM:1017983/C2/1> wherein R and R1 are the same or different, C1 t C4 alkyl, halogenated C1 to C4 alkyl, C2 to C4 alkenyl, C1 to C4 alkoxy-substituted C2 to C4 alkenyl, C1 to C4 alkylmercapto-substituted C2 to C4 alkenyl, cycloalkyl, C1 to C4 alkoxy, aralkyl, or aryl; and R may also be C1 to C4 alkylamino, di-C1 to C4 alkyl amino, or di-C1 to C4 alkenyl amino; R11 is hydrogen, alkyl, phenyl, halogenated phenyl, nitro-substituted phenyl, C1 to C4 alkyl substituted-, or C1 to C4 alkoxy substituted-, or C1 to C4 alkylmercapto-or di-C1 to C4 alkylamino substituted phenyl or a 5- or 6-membered O, S, or N containing heterocycle; R111 is hydrogen, or alkyl, with the proviso that if R111 is alkyl, R11 must be alkyl; and X is O or S. The compounds are prepared by reacting the corresponding phosphorus acid halide with appropriate 2-hydroxy-1,3-thiazoles, suitably in organic solvent in the presence of an acid binding agent; suitable solvents are low molecular weight alkanols, ethers, ketones, or nitriles, or aliphatic or aromatic, optionally chlorinated hydrocarbons. Acid binding agents may be alkali metal carbonates or alcoholates, or tertiary amines; alternatively salts (e.g. alkali metal or ammonium) of the thiazoles may be used without an acid binding agent. Examples are given for many compounds of the invention; they are useful as insecticides (see Division A5) and also as plasticizers and lubricant additives.ALSO:Insecticidal compositions comprise an inert diluent or carrier, with esters of phosphorus acids of formula: <FORM:1017983/A5-A6/1> wherein R and R1 are the same or different C1 to C4 alkyl, halogenated C1 to C4 alkyl, C2 to C4 alkenyl, C1 to C4 alkoxy-substituted C2 to C4 alkenyl, C1 to C4 alkylmercapto substituted C2 to C4 alkenyl, cycloalkyl, C1 to C4 alkoxy, aralkyl or aryl; and R may also be C1 to C4 alkyl amino, di-C1 to C4 alkylamino, or di-C1 to C4 alkenyl amino; R is hydrogen, alkyl, phenyl, halogenated phenyl, nitro-substituted phenyl, C1 to C4 alkyl substituted, or C1 to C4 alkoxy substituted-, or C1 to C4 alkyl mercapto substituted-or di-C1 to C4 alkyl amino substituted-phenyl, or a S- or 6-membered O, S, or N containing heterocycle; R111 is hydrogen, or alkyl, with the proviso that if R111 is alkyl, R11 must, also be alkyl; and X is S or O. Suitable carriers are liquid or solid e.g. talc, chalk, bentonite, clay, water with an emulsifier, alcohols, ketones, or liquid hydrocarbons, and the compositions may contain other known fertilisers and/or insecticides. An example is given for a composition of: O, O-diethyl-thiono-phosphoric acid-0-[4-phenyl-thiazolyl-(2)-] ester, and also the corresponding 4-(3-nitrophenyl)-compound, with an equal weight of dimethylformamide, and 20% of a benzyl hydroxypolyglycol ether (referred to the weight of active ingredient) as emulsifier, the concentrate being appropriately diluted with water before use. The preparation of the esters is widely exemplified, (see Division C2).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF38814A DE1232151B (en) | 1963-01-22 | 1963-01-22 | Process for the preparation of phosphorus-containing thiazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1017983A true GB1017983A (en) | 1966-01-26 |
Family
ID=7097502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB278164A Expired GB1017983A (en) | 1963-01-22 | 1964-01-22 | Pesticidal heterocyclic phosphorus acid esters |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE642763A (en) |
| CH (1) | CH431534A (en) |
| DE (1) | DE1232151B (en) |
| GB (1) | GB1017983A (en) |
| NL (1) | NL6400465A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3518279A (en) * | 1967-08-29 | 1970-06-30 | American Cyanamid Co | Thiazolylphenyl phosphates |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2725328A (en) * | 1954-08-30 | 1955-11-29 | Hercules Powder Co Ltd | 2, 3-p-dioxanedithiol-s, s-bis (o, o-dialkylphosphorodithioate) |
-
1963
- 1963-01-22 DE DEF38814A patent/DE1232151B/en active Pending
-
1964
- 1964-01-10 CH CH24864A patent/CH431534A/en unknown
- 1964-01-21 BE BE642763A patent/BE642763A/xx unknown
- 1964-01-22 NL NL6400465A patent/NL6400465A/xx unknown
- 1964-01-22 GB GB278164A patent/GB1017983A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL6400465A (en) | 1964-07-23 |
| BE642763A (en) | 1964-07-22 |
| CH431534A (en) | 1967-03-15 |
| DE1232151B (en) | 1967-01-12 |
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