GB887676A - Thiophosphoric acid esters - Google Patents
Thiophosphoric acid estersInfo
- Publication number
- GB887676A GB887676A GB21456/59A GB2145659A GB887676A GB 887676 A GB887676 A GB 887676A GB 21456/59 A GB21456/59 A GB 21456/59A GB 2145659 A GB2145659 A GB 2145659A GB 887676 A GB887676 A GB 887676A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oc2h5
- lower alkyl
- och3
- dihydro
- oxo
- 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
- 150000003580 thiophosphoric acid esters Chemical class 0.000 title abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 3
- MPNCUZYHDJMSKN-UHFFFAOYSA-N 5-(chloromethyl)-1H-pyridazin-6-one Chemical compound ClCC=1C(NN=CC1)=O MPNCUZYHDJMSKN-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 2
- 239000004480 active ingredient Substances 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- HYWSGXJJXVTMIA-UHFFFAOYSA-N 2-(hydroxymethyl)-1,5-dihydropyridazin-6-one Chemical compound OCN1NC(CC=C1)=O HYWSGXJJXVTMIA-UHFFFAOYSA-N 0.000 abstract 1
- PSTZUHXFPSZKDS-UHFFFAOYSA-N 5-bromo-4-chloro-2-(chloromethyl)pyridazin-3-one Chemical compound BrC1=C(C(N(N=C1)CCl)=O)Cl PSTZUHXFPSZKDS-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000005909 Kieselgur Substances 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000000895 acaricidal effect Effects 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000006203 ethylation Effects 0.000 abstract 1
- 238000006200 ethylation reaction Methods 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 230000011987 methylation Effects 0.000 abstract 1
- 238000007069 methylation reaction Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000001069 nematicidal effect Effects 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000000361 pesticidal effect Effects 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
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650905—Six-membered rings having the nitrogen atoms in the positions 1 and 2
-
- 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
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650905—Six-membered rings having the nitrogen atoms in the positions 1 and 2
- C07F9/650947—Six-membered rings having the nitrogen atoms in the positions 1 and 2 condensed with carbocyclic rings or carbocyclic ring systems
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)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention comprises thiophosphoric acid esters of the general formula <FORM:0887676/IV (b)/1> wherein R and R1 are lower alkyl radicals having less than 5 carbon atoms, A is an oxygen or sulphur atom, Z is hydrogen, hydroxy, halogen, phenyl, OCH3, OC2H5, -O-C(O)CH3, O-P(S)(OC2H5)2, O-P(S)(OCH3)2, or a lower alkyl radical having less than 5 carbon atoms, X and Y each represent hydrogen, halogen, phenyl, or a lower alkyl radical having less than 5 carbon atoms, or X and Y when taken together represent the remainder of a benzene ring. The products may be obtained by reacting a salt of an appropriate dialkyl phosphorothioate with an appropriate chloromethyl pyridazone. Certain of the products may also be obtained by first preparing a compound of the above general formula in which Z is OH and then subjecting this compound to methylation, ethylation or esterification to form the products in which Z is OCH3, OC2H5, O.CO.CH3, OP(S)(OC2H5)2 and OP(S)(OCH3)2. Examples are given for the production of compounds of the above formula in which R and R1 are each ethyl and A is sulphur and Z is OH, CH3, -OCH3Cl, O.C(O)CH3, and O.P(S)(OC2H5)2 respectively and X and Y are each hydrogen and of the compounds 0,0-diethyl S - (4 - bromo - 5 - chloro - 1,6 - dihydro - 6 - oxo - 1 - pyridazinylmethyl) phosphorodithioate, 0,0 - diethyl S - (1,6 - dihydro - 4,5 - dimethyl - 3 - hydroxy - 6 - oxo - 1 - pyridazinylmethyl) phosphorodithioate, 0,0 - dimethyl S - (3 - chloro - 1,6 - dihydro - 6 - oxo - 1 - pyridazinyl-methyl) phosphorodithioate, 0,0 - diethyl S -(4 - chloro - 1,2 - dihydro - 1 - oxo - 2 - phthalazinyl methyl) phosphorodithioate and 0,0 - diethyl S - (3 - chloro 1,6 - dihydro - 6 - oxo - 1 - pyridazinylmethyl) phosphorothioate. Other typical products are also specified. The products have pesticidal properties (see Group VI). The chlormethyl pyridazones used as starting materials may be obtained by reacting the corresponding N-hydroxymethyl pyridazone with thionyl chloride and the preparation of 5-bromo-4-chloro-2-chloromethyl 3-pyridazone is described.ALSO:An insecticidal, acaricidal or nematocidal composition comprises as active ingredient a compound of the general formula <FORM:0887676/VI/1> in which R and R1 represent lower alkyl radicals, A is oxygen or sulphur, Z is hydrogen, hydroxy, halogen, phenyl, OCH3, OC2H5, O.C(O)CH3, OP(S)(OCH3)2, O.P(S)(OC2H5)2 or a lower alkyl radical, X and Y represent hydrogen, halogen, phenyl, or a lower alkyl radical, or when taken together X and Y represent the remainder of a benzene ring, said lower alkyl radicals having less than 5 carbon atoms (see Group IV (b)). The active ingredient may be used as a spray in an organic solvent, as an emulsion in water or other non-solvent, or on a solid carrier such as a talc, clay or diatomaceous earth.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74529958A | 1958-06-30 | 1958-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB887676A true GB887676A (en) | 1962-01-24 |
Family
ID=24996108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21456/59A Expired GB887676A (en) | 1958-06-30 | 1959-06-23 | Thiophosphoric acid esters |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE580175A (en) |
| CH (1) | CH384581A (en) |
| DE (1) | DE1106766B (en) |
| FR (1) | FR1231293A (en) |
| GB (1) | GB887676A (en) |
| NL (2) | NL240737A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2413323A1 (en) * | 1977-12-30 | 1979-07-27 | American Cyanamid Co | Shaped alumina particles for catalysts - obtd. by passing an aq. rehydratable alumina slurry through a heated shaping medium |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE927270C (en) * | 1953-02-26 | 1955-05-02 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
| NL93955C (en) * | 1955-03-21 | 1900-01-01 | ||
| NL93954C (en) * | 1955-03-21 | 1900-01-01 |
-
0
- NL NL110640D patent/NL110640C/xx active
- BE BE580175D patent/BE580175A/xx unknown
- NL NL240737D patent/NL240737A/xx unknown
-
1959
- 1959-06-23 GB GB21456/59A patent/GB887676A/en not_active Expired
- 1959-06-26 FR FR798596A patent/FR1231293A/en not_active Expired
- 1959-06-29 CH CH7505959A patent/CH384581A/en unknown
- 1959-06-30 DE DEA32364A patent/DE1106766B/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL110640C (en) | 1900-01-01 |
| NL240737A (en) | 1900-01-01 |
| CH384581A (en) | 1964-11-30 |
| BE580175A (en) | 1900-01-01 |
| FR1231293A (en) | 1960-09-28 |
| DE1106766B (en) | 1961-05-18 |
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