GB1104595A - Thiolphosphoric acid esters - Google Patents
Thiolphosphoric acid estersInfo
- Publication number
- GB1104595A GB1104595A GB4469466A GB4469466A GB1104595A GB 1104595 A GB1104595 A GB 1104595A GB 4469466 A GB4469466 A GB 4469466A GB 4469466 A GB4469466 A GB 4469466A GB 1104595 A GB1104595 A GB 1104595A
- Authority
- GB
- United Kingdom
- Prior art keywords
- substituted
- alkyl
- halogen atoms
- reaction
- 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 abstract 5
- 150000002148 esters Chemical class 0.000 title abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- 125000005843 halogen group Chemical group 0.000 abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 239000003085 diluting agent Substances 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000004480 active ingredient Substances 0.000 abstract 2
- 230000002464 fungitoxic effect Effects 0.000 abstract 2
- 229910052739 hydrogen Chemical group 0.000 abstract 2
- 239000001257 hydrogen Chemical group 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 2
- 239000000843 powder Substances 0.000 abstract 2
- 241000233866 Fungi Species 0.000 abstract 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 239000003899 bactericide agent Substances 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- -1 benzyl halide Chemical class 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 239000000428 dust Substances 0.000 abstract 1
- 239000004495 emulsifiable concentrate Substances 0.000 abstract 1
- 239000000417 fungicide Substances 0.000 abstract 1
- 231100000162 fungitoxic Toxicity 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 239000002480 mineral oil Substances 0.000 abstract 1
- 235000010446 mineral oil Nutrition 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 239000007921 spray Substances 0.000 abstract 1
- 239000004094 surface-active agent Substances 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1653—Esters of thiophosphoric acids with arylalkanols
-
- 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
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Novel thiolphosphoric acid esters of the general formula <FORM:1104595/C2/1> in which R1 is C1-C6 alkyl which may be substituted by one or more halogen atoms, or is a cycloalkyl radical which may be substituted by C1-C4 alkyl radicals, R2 is C1-C6 alkyl which may be substituted by one or more halogen atoms, R3 is CH3 or CH3O and R4 is CH3, CH3O or hydrogen are obtained by reacting a benzyl halide of the formula <FORM:1104595/C2/2> with a compound of the formula (R1O)(R2O) P(O)SH either in the form of its salt or as the free acid in which case the reaction is carried out in the presence of an acid-binding agent, e.g. an alkali metal carbonate or alcoholate or a tertiary base, e.g. triethylamine, pyridine or dimethylaniline. The reaction temperature is suitably between 30 DEG and 80 DEG C. and the reaction is preferably carried out in a solvent or diluent. The products have fungitoxic properties (see Division A5).ALSO:A fungitoxic composition comprises a liquid or solid diluent or carrier in admixture with, as active ingredient, a thiolphosphoric acid ester of the general formula: <FORM:1104595/A5-A6/1> in which R1 is C1-C6 alkyl which may be substituted by one or more halogen atoms, or is a cycloalkyl radical which may be substituted by C1-C4 alkyl radicals, R2 is C1-C6 alkyl which may be substituted by one or more halogen atoms, R3 is methyl or methoxy and R4 is methyl, methoxy or hydrogen. Other unspecified fungicides, herbicides, insecticides and bactericides may be present and surface active agents and dispersing agents may also be included. The active ingredient or composition containing it may be applied to a fungous habitat or to crops liable to fungous attack for combating fungi. Specified liquid diluents are aromatic hydrocarbons which may be chlorinated, paraffins, e.g. mineral oil fractions, alcohols, amines, e.g. ethanolamine, dimethyl formamide, and water. The composition may be in the form of an emulsifiable concentrate, spray powder, soluble powder, dust or granulate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1965F0047699 DE1239296B (en) | 1965-11-17 | 1965-11-17 | Process for the preparation of Thiolphorsäureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1104595A true GB1104595A (en) | 1968-02-28 |
Family
ID=7101786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4469466A Expired GB1104595A (en) | 1965-11-17 | 1966-10-06 | Thiolphosphoric acid esters |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT258960B (en) |
| BE (1) | BE689777A (en) |
| DE (1) | DE1239296B (en) |
| DO (1) | DOP1966001305A (en) |
| ES (1) | ES333362A1 (en) |
| FR (1) | FR1501312A (en) |
| GB (1) | GB1104595A (en) |
| NL (1) | NL6615901A (en) |
-
1965
- 1965-11-17 DE DE1965F0047699 patent/DE1239296B/en active Pending
-
1966
- 1966-10-06 GB GB4469466A patent/GB1104595A/en not_active Expired
- 1966-10-17 AT AT968266A patent/AT258960B/en active
- 1966-10-26 DO DO1966001305A patent/DOP1966001305A/en unknown
- 1966-11-10 NL NL6615901A patent/NL6615901A/xx unknown
- 1966-11-15 ES ES0333362A patent/ES333362A1/en not_active Expired
- 1966-11-16 BE BE689777D patent/BE689777A/xx unknown
- 1966-11-17 FR FR83993A patent/FR1501312A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL6615901A (en) | 1967-05-18 |
| DE1239296B (en) | 1967-04-27 |
| FR1501312A (en) | 1967-11-10 |
| ES333362A1 (en) | 1967-07-16 |
| DOP1966001305A (en) | 1973-07-30 |
| BE689777A (en) | 1967-05-16 |
| AT258960B (en) | 1967-12-27 |
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