ES265152A1 - New insecticidal thiophosphoric acid esters and their manufacture - Google Patents
New insecticidal thiophosphoric acid esters and their manufactureInfo
- Publication number
- ES265152A1 ES265152A1 ES0265152A ES265152A ES265152A1 ES 265152 A1 ES265152 A1 ES 265152A1 ES 0265152 A ES0265152 A ES 0265152A ES 265152 A ES265152 A ES 265152A ES 265152 A1 ES265152 A1 ES 265152A1
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- carbon atoms
- residue containing
- atom
- hydrogen atom
- 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
- 230000000749 insecticidal effect Effects 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000003580 thiophosphoric acid esters Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 10
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 229920002678 cellulose Polymers 0.000 abstract 2
- 239000001913 cellulose Substances 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 230000000361 pesticidal effect Effects 0.000 abstract 2
- 239000003208 petroleum Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 239000012298 atmosphere Substances 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 238000010410 dusting Methods 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 239000002316 fumigant Substances 0.000 abstract 1
- 239000000417 fungicide Substances 0.000 abstract 1
- -1 gaseous Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000003701 inert diluent Substances 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 239000003350 kerosene Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 150000002903 organophosphorus compounds Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 238000005507 spraying Methods 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000002699 waste material Substances 0.000 abstract 1
- 239000000080 wetting agent 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
- C07F9/06—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
-
- 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
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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0923702/IV(a)/1> in which R and R1 and alkyl, cycloalkyl, aralkyl, aryl or heterocyclic residues which may be substituted and which alkyl residue may be interrupted by at least one oxygen atom, R2 is a hydrogen atom or an alkyl or acyl residue containing at most 4 carbon atoms, R3 is a hydrogen atom or an alkyl residue containing at most 4 carbon atoms, R4 is the group -CH2-, -CH2-CH2- or -CH(R5)- in which R5 is an alkyl residue containing at most 4 carbon atoms and X is an oxygen or sulphur atom. They may be obtained by reacting a compound of formula (RO)(R1O)P(X)SMe in which Me is a salt-forming cation, especially in alkali metal, with a compound of the formula Hal.R4.CON(OR2) (R3) in which Hal is a halogen atom, e.g. Br or Cl. The reaction may be effected at ordinary or elevated temperature, e.g. within the range of 0 DEG to 120 DEG C. and an inert solvent, e.g. an alcohol or ketone, may be present, or water may be added. If desired the reaction may be carried out in an atmosphere of an inert gas, e.g. nitrogen, and/or under reduced pressure. Several examples are given and the products have pesticidal properties (see Group VI).ALSO:A pesticidal composition comprises, in admixture with a liquid, gaseous, or solid diluent, an organo-phosphorus compound of the general formula <FORM:0923702/VI/1> in which R and R1 each represent an alkyl, cycloalkyl, aralkyl, aryl or heterocyclic residue which may be substituted and which alkyl residue may be interrupted by at least one oxygen atom, R2 is a hydrogen atom or an alkyl or acyl residue containing at most 4 carbon atoms, R3 is a hydrogen atom or an alkyl residue containing at most 4 carbon atoms, R4 represents the group -CH2-, -CH2, -CH2-, or <FORM:0923702/VI/2> in which R5 is an alkyl residue containing at most 4 carbon atoms, and X is an oxygen or a sulphur atom. The composition may be in the form of a spraying or dusting preparation and is suitably in the form of a solution, suspension, or emulsion which may be prepared with wetting agents, adhesives, water and/or an organic solvent, e.g. alcohol, acetone, methyl-cyclohexanol, benzene, kerosene, petroleum, or petroleum fractions. Besides the usual inert diluents the composition may contain sulphite cellulose waste liquor or cellulose derivatives. The active ingredient may also be used in vapour form as a fumigant. Other insecticides and/or fungicides may also be present.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH207560A CH392980A (en) | 1960-02-24 | 1960-02-24 | Pesticides containing organic phosphorus compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES265152A1 true ES265152A1 (en) | 1961-08-16 |
Family
ID=4225310
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0265152A Expired ES265152A1 (en) | 1960-02-24 | 1961-02-23 | New insecticidal thiophosphoric acid esters and their manufacture |
Country Status (6)
| Country | Link |
|---|---|
| CH (1) | CH392980A (en) |
| DE (1) | DE1194633B (en) |
| ES (1) | ES265152A1 (en) |
| FR (1) | FR1285497A (en) |
| GB (1) | GB923702A (en) |
| NL (2) | NL261594A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3350192A (en) * | 1963-12-11 | 1967-10-31 | Velsicol Chemical Corp | Method for pre-emergence control of undesirable plant life |
| US3342906A (en) * | 1964-08-04 | 1967-09-19 | Velsicol Chemical Corp | O-ethyl-s-[n'-methoxy-n'-methyl-acetamido]-n-isopropylthio-phosphoramide |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1060659B (en) * | 1955-02-16 | 1959-07-02 | Montedison Spa | Pest repellants |
| DE1022579B (en) * | 1956-04-21 | 1958-01-16 | Bayer Ag | Process for the preparation of insecticidally active thiophosphoric acid esters or dithiophosphoric acid esters |
-
0
- NL NL133769D patent/NL133769C/xx active
- NL NL261594D patent/NL261594A/xx unknown
-
1960
- 1960-02-24 CH CH207560A patent/CH392980A/en unknown
-
1961
- 1961-02-20 FR FR853219A patent/FR1285497A/en not_active Expired
- 1961-02-23 DE DE1961C0023483 patent/DE1194633B/en active Pending
- 1961-02-23 ES ES0265152A patent/ES265152A1/en not_active Expired
- 1961-02-24 GB GB694961A patent/GB923702A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1285497A (en) | 1962-02-23 |
| NL133769C (en) | |
| NL261594A (en) | |
| GB923702A (en) | 1963-04-18 |
| DE1194633B (en) | 1965-06-10 |
| CH392980A (en) | 1965-05-31 |
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