GB932388A - New thiophosphoric acid esters and pesticidal compositions containing them - Google Patents

New thiophosphoric acid esters and pesticidal compositions containing them

Info

Publication number
GB932388A
GB932388A GB13940/59A GB1394059A GB932388A GB 932388 A GB932388 A GB 932388A GB 13940/59 A GB13940/59 A GB 13940/59A GB 1394059 A GB1394059 A GB 1394059A GB 932388 A GB932388 A GB 932388A
Authority
GB
United Kingdom
Prior art keywords
atom
ring
sulphur
substituents
oxygen
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
Application number
GB13940/59A
Inventor
Edward Sherlock
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to BE572314D priority Critical patent/BE572314A/xx
Priority to NL103644D priority patent/NL103644C/xx
Priority to NL111238D priority patent/NL111238C/xx
Priority to DEJ17863A priority patent/DE1245206B/en
Priority to DEI15546A priority patent/DE1118789B/en
Priority to CH6539358A priority patent/CH374689A/en
Priority to FR777508A priority patent/FR1219238A/en
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB13940/59A priority patent/GB932388A/en
Priority to GB13939/59A priority patent/GB913334A/en
Priority to GB16716/59A priority patent/GB917420A/en
Priority to US21133A priority patent/US3185699A/en
Priority to CH454260A priority patent/CH385224A/en
Priority to CH454160A priority patent/CH380734A/en
Priority to DEJ18006A priority patent/DE1132560B/en
Priority to FR825171A priority patent/FR77866E/en
Priority to FR825170A priority patent/FR77659E/en
Priority to US25563A priority patent/US3134775A/en
Priority to CH551160A priority patent/CH380735A/en
Priority to DEJ20952A priority patent/DE1217695B/en
Priority to DEJ18119A priority patent/DE1159462B/en
Priority to FR827349A priority patent/FR78060E/en
Priority to GB36878/62A priority patent/GB1063072A/en
Priority to US290196A priority patent/US3169964A/en
Publication of GB932388A publication Critical patent/GB932388A/en
Priority to FR968354A priority patent/FR85612E/en
Priority to US431726A priority patent/US3270031A/en
Priority to US431725A priority patent/US3243437A/en
Priority to SE5172/65A priority patent/SE320379B/xx
Expired legal-status Critical Current

Links

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 System
    • 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
    • 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 System
    • 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
    • C07F9/6503—Five-membered rings
    • C07F9/65031—Five-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 System
    • 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
    • C07F9/6503—Five-membered rings
    • C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
    • 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 System
    • 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
    • C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
    • 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 System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
    • C07F9/6521—Six-membered rings
    • 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 System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6524—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having four or more nitrogen atoms as the only ring hetero atoms

Abstract

The invention comprises compounds of the formula:-<FORM:0932388/IV(a)/1> in which R1 and R11 are C1-C4 alkyl radicals, X is an atom of oxygen or sulphur, and Z together with the adjacent N atom and the adjacent carbon atom constitute a substituted or unsubstituted 5- or 6-membered aromatic heterocyclic ring, said ring containing at least one atom of nitrogen, oxygen, or sulphur in addition to the nitrogen atom depicted, and salts of said compounds. Specified heterocyclic rings are imidazole, pyrazole, triazole, tetrazole, pyrazine, pyridazine, pyrimidine, a triazine, thiazole, thiadiazole, oxazole, and isoxazole. The heterocyclic ring may contain one or more substituents, e.g. alkyl, cycloalkyl, aryl, nitroaryl, or aralkyl radicals, or amino, hydroxy, or carboxylic ester groups and the substituents can be carried by either carbon or nitrogen atoms in the ring. The preferred salts of the products are acid addition salts, e.g. oxalates or hydrochlorides. The compounds may be obtained by reacting a compound of the formula <FORM:0932388/IV(a)/2> with a compound of the formula (R1O)(R11O)P(X)SM wherein Y is Cl, Br or I and M is an alkali metal, e.g. Na, or K, or an ammonium radical. The process is conveniently effected by using a solution or dispersion of the reactants in a suitable inert organic solvent e.g. methanol, ethanol, acetone or dioxane. Reaction temperatures may vary from room temperature to e.g. 100 DEG C. and it is convenient to reflux a solution of the reactants in the organic solvent. Several examples are given and the products have pesticidal properties (see Group VI). The Provisional Specification includes examples for the production of the compounds:- <FORM:0932388/IV(a)/3> Specification 899,701 is referred to.ALSO:A pesticidal composition comprises a suitable diluent or carrier and as active ingredient a compound of the formula <FORM:0932388/VI/1> in which R1 and R11 are C1-C4 alkyl radicals, X is an atom of oxygen or sulphur and Z together with the adjacent N atom and the adjacent C atom constitute a substituted or unsubstituted 5- or 6-membered aromatic heterocyclic ring, said ring containing at least one atom of nitrogen, oxygen or sulphur in addition to the N atom depicted, or a salt of such compound, especially an acid addition salt e.g. an oxalate or hydrochloride (see Group IV (b)). Specified heterocyclic rings are imidazole, pyrazole, triazole, tetrazole, pyrazine, pyridazine, pyrimidine, triazine, thiazole, thiadiazole oxazole and isoxazole. The heterocyclic ring may contain one or more substituents e.g. alkyl, cycloalkyl, aryl, nitroaryl, amino, hydroxy or carboxylic ester groups and the substituents can be carried by either carbon or nitrogen atoms in the ring. The composition may be in the form of a liquid or powder and may contain a wetting or dispersing agent. Specified diluents or carriers are water, methanol, tetrahydrofurfuryl alcohol, diacetone alcohol, b -ethoxy ethanol, fuller's earth, talc, kaolin, kieselguhr and bentonite. Specification 899,701 is referred to.
GB13940/59A 1957-10-25 1959-04-23 New thiophosphoric acid esters and pesticidal compositions containing them Expired GB932388A (en)

Priority Applications (27)

Application Number Priority Date Filing Date Title
BE572314D BE572314A (en) 1957-10-25
NL103644D NL103644C (en) 1957-10-25
NL111238D NL111238C (en) 1957-10-25
DEJ17863A DE1245206B (en) 1957-10-25 1958-10-23 Insect repellants
DEI15546A DE1118789B (en) 1957-10-25 1958-10-23 Process for the preparation of 1, 3, 5-triazine derivatives
CH6539358A CH374689A (en) 1957-10-25 1958-10-24 Process for the preparation of new s-triazine derivatives
FR777508A FR1219238A (en) 1957-10-25 1958-10-24 S-triazine derivatives, for example 2-dialkoxyphosphinothioylthiomethyl-4.6-diamino-s-triazine and process for their manufacture
GB13940/59A GB932388A (en) 1959-04-23 1959-04-23 New thiophosphoric acid esters and pesticidal compositions containing them
GB13939/59A GB913334A (en) 1957-10-25 1959-04-23 New organo-phosphorus s-triazine compounds and their use as pesticides
GB16716/59A GB917420A (en) 1957-10-25 1959-05-15 Organo-polymers s-triazine derivatives and pesticidal compositions containing them
US21133A US3185699A (en) 1957-10-25 1960-04-11 Heterocyclic phosphorothioates
DEJ18006A DE1132560B (en) 1957-10-25 1960-04-22 Process for the preparation of 1, 3, 5-triazine derivatives
CH454160A CH380734A (en) 1957-10-25 1960-04-22 Process for the preparation of new s-triazine derivatives
CH454260A CH385224A (en) 1957-10-25 1960-04-22 Process for the preparation of new heterocyclic compounds
FR825171A FR77866E (en) 1957-10-25 1960-04-23 S-triazine derivatives, for example 2-dialkoxyphosphinothioylthiomethyl-4-6-diamino-s-triazine and process for their manufacture
FR825170A FR77659E (en) 1957-10-25 1960-04-23 S-triazine derivatives, for example 2-dialkoxyphosphinothioylthiomethyl-4-6-diamino-s-triazine and process for their manufacture
US25563A US3134775A (en) 1957-10-25 1960-04-29 New pesticidal triazine derivatives
CH551160A CH380735A (en) 1957-10-25 1960-05-13 Process for the preparation of new s-triazine derivatives
DEJ20952A DE1217695B (en) 1957-10-25 1960-05-13 Insecticides with acaricidal properties
DEJ18119A DE1159462B (en) 1957-10-25 1960-05-13 Process for the preparation of s-triazine derivatives
FR827349A FR78060E (en) 1957-10-25 1960-05-16 S-triazine derivatives, for example 2-dialkoxy phosphinothioylthiomethyl-4-6-diamino-s-triazine and process for their manufacture
GB36878/62A GB1063072A (en) 1957-10-25 1962-09-28 Organo-phosphorus s-triazine derivatives
US290196A US3169964A (en) 1957-10-25 1963-06-24 Triazine derivatives possessing aphicidal properties
FR968354A FR85612E (en) 1957-10-25 1964-03-23 S-triazine derivatives, for example 2-dialkoxy-phosphinothioylthiomethyl-4-6-diamino-s-triazine and process for their manufacture
US431726A US3270031A (en) 1957-10-25 1965-02-10 Certain tetrazolylmethyl phosphorothioates
US431725A US3243437A (en) 1957-10-25 1965-02-10 Pyrimidine phosphorothioates
SE5172/65A SE320379B (en) 1957-10-25 1965-04-21

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB13940/59A GB932388A (en) 1959-04-23 1959-04-23 New thiophosphoric acid esters and pesticidal compositions containing them

Publications (1)

Publication Number Publication Date
GB932388A true GB932388A (en) 1963-07-24

Family

ID=10032135

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13940/59A Expired GB932388A (en) 1957-10-25 1959-04-23 New thiophosphoric acid esters and pesticidal compositions containing them

Country Status (1)

Country Link
GB (1) GB932388A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3432519A (en) * 1965-05-18 1969-03-11 Rhone Poulenc Sa Certain 3-substituted-5-thiophosphorylmethyl-1,2,4-oxadiazoles
US4211703A (en) 1976-11-02 1980-07-08 Smithkline Corporation Phosphonoalkyl and esterified phosphonoalkyl substituted tetrazole thiols
US4425338A (en) 1982-03-31 1984-01-10 Union Carbide Corporation Alpha-heterocyclic carbinol phosphates
US4618603A (en) * 1982-03-31 1986-10-21 Union Carbide Corporation Alpha-heterocyclic carbinol phosphates
US4839349A (en) * 1988-06-03 1989-06-13 Uniroyal Chemical Company, Inc. Phosphorus substituted tetrazolinones and pesticidal use
US5049554A (en) * 1983-11-16 1991-09-17 Uniroyal Chemical Company, Inc. Phosphorous substituted tetrazolinones and insecticidal use thereof

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3432519A (en) * 1965-05-18 1969-03-11 Rhone Poulenc Sa Certain 3-substituted-5-thiophosphorylmethyl-1,2,4-oxadiazoles
US4211703A (en) 1976-11-02 1980-07-08 Smithkline Corporation Phosphonoalkyl and esterified phosphonoalkyl substituted tetrazole thiols
US4425338A (en) 1982-03-31 1984-01-10 Union Carbide Corporation Alpha-heterocyclic carbinol phosphates
US4618603A (en) * 1982-03-31 1986-10-21 Union Carbide Corporation Alpha-heterocyclic carbinol phosphates
US5049554A (en) * 1983-11-16 1991-09-17 Uniroyal Chemical Company, Inc. Phosphorous substituted tetrazolinones and insecticidal use thereof
US4839349A (en) * 1988-06-03 1989-06-13 Uniroyal Chemical Company, Inc. Phosphorus substituted tetrazolinones and pesticidal use

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