GB899701A - New phosphorus-containing organic compounds - Google Patents

New phosphorus-containing organic compounds

Info

Publication number
GB899701A
GB899701A GB33358/57A GB3335857A GB899701A GB 899701 A GB899701 A GB 899701A GB 33358/57 A GB33358/57 A GB 33358/57A GB 3335857 A GB3335857 A GB 3335857A GB 899701 A GB899701 A GB 899701A
Authority
GB
United Kingdom
Prior art keywords
formula
triazine
compound
amino
methyl
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
GB33358/57A
Inventor
Alan Calderbank
Eric Callander Edgar
John Arthur Silk
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 NL111238D priority patent/NL111238C/xx
Priority to NL103644D priority patent/NL103644C/xx
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB33358/57A priority patent/GB899701A/en
Priority to DEI15546A priority patent/DE1118789B/en
Priority to DEJ17863A priority patent/DE1245206B/en
Priority to CH6539358A priority patent/CH374689A/en
Priority to FR777508A priority patent/FR1219238A/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 DEJ18006A priority patent/DE1132560B/en
Priority to CH454260A priority patent/CH385224A/en
Priority to CH454160A priority patent/CH380734A/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
Publication of GB899701A publication Critical patent/GB899701A/en
Priority to GB36878/62A priority patent/GB1063072A/en
Priority to US290196A priority patent/US3169964A/en
Priority to FR968354A priority patent/FR85612E/en
Priority to US394372A priority patent/US3169904A/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

    • 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
    • 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
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon 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
    • C07F9/6503—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 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
    • C07F9/6503—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 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
    • C07F9/6512—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 Table
    • 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 Table
    • 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
    • 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
    • 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
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Dentistry (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention comprises s-triazine derivatives of the formula <FORM:0899701/IV (b)/1> wherein R1 and R2 are methyl or ethyl radicals, R3, R4, R5 and R6 which can be the same or different are hydrogen, or methyl, ethyl, propyl or butyl radicals or R3 and R4 or R5 and R6\t together with the adjacent N atom constitute a piperidino ring and X is an oxygen or sulphur atom, and acid addition salts thereof. The acid addition salts may be salts of inorganic or organic acids, e.g. hydrochlorides, oxalates, p-toluene sulphonates, methane sulphonates or isethionates. The s-triazine derivatives may be obtained by reacting a compound of the formula (R1O)(R2O)P(X)SM wherein R1, R2, and X hav the meanings stated above and M is an alkali metal, e.g. sodium, or an ammonium radical, with a compound of the formula <FORM:0899701/IV (b)/2> wherein R3, R4, R5 and R6 are as defined above and Y is a halogen atom, e.g. Cl, Br, or I. Suitable reaction temperatures are between 20 DEG C. and 150 DEG C. and an inert solvent or diluent, e.g. methanol or ethanol, may be present. Products in which at least one of the radicals R3, R4, R5 and R6 is hydrogen may also be obtained by reacting a compound of the formula <FORM:0899701/IV (b)/3> wherein R1, R2 and X are as defined above and R7 is a lower alkyl radical with a biguanide of the formula <FORM:0899701/IV (b)/4> wherein R3, R4, R5, and R6 are as defined above, at least one of them being hydrogen. This reaction may also be carried out in a solvent or inert diluent, e.g. methanol. Several examples are given. The products have insecticidal properties (see Group VI) the particularly preferred compounds being 2-dimethoxyphosphinothioylthiomethyl-4 : 6-diamino-s-triazine and 2-dimethoxyphosphinothioylthiomethyl - 4 - amino - 6-methylamino-s-triazine and their acid addition salts. The halomethyl-s-triazines used as starting materials may be obtained by reacting a compound of the formula Y.CH2-COOR7 wherein Y and R7 are as defined above with a biguanide of the above formula in which at least one of R3, R4, R5, and R6 is hydrogen, or by reaction of the corresponding diazo-methyl-s-triazine derivative with gaseous hydrogen halide, e.g. gaseous HCl. Examples are given for the production of 2-chloromethyl-4 : 6-bis(methylamino)-s-triazine and the corresponding 4-amino-6-methylamino, 4-amino-6-dimethylamino, and -4-amino-6-piperidino compounds, and of 2-bromomethyl-4- : 6-diamino-s-triazine and the corresponding 2-iodomethyl compound. The O,O1-dialkyl S-alkoxycarbonylmethyl phosthorothiolates and thiolothionates also used as starting materials may be obtained by reacting a compound of the formula (R1O)(R2O)P(X)SM wherein R1, R2, X and M are as defined above with a compound of the formula Y.CH2.COOR7 wherein R7 and Y are as defined above and examples are given for the production of O,O1-diethyl S - ethoxycarbonylmethyl phosphoro - thiolothionate and O,O1 - diethyl S - ethoxycarbonylmethyl phosphorothiolate. According to the Provisional Specification the radicals R3 and R4 or R5 and R6 in the triazine products may be joined together with the adjacent nitrogen atom to form a morpholino ring.ALSO:An insecticidal composition contains in admixture with a suitable carrier or diluent a compound of the formula <FORM:0899701/VI/1> wherein R1 and R2 are methyl or ethyl radicals, R3, R4, R5 and R6 which can be the same or different are hydrogen, or methyl, ethyl, propyl or butyl radicals, or R3 and R4, or R5 and R6, together with the adjacent nitrogen atom constitute a piperidino ring, or an acid addition salt of such compound. The acid addition salt may be a salt of an inorganic or organic acid, e.g. a hydrochloride, oxalate, p-toluene sulphonate, methane sulphonate, or isethionate. The composition may be in the form of an aqueous formulation which may contain an organic solvent, e.g. methanol, tetrahydrofurfuryl alcohol or b -ethoxyethanol, or in the form of a powder in which the carrier is an inert pulverulent solid. The composition may also contain a wetting or dispersing agent or other auxiliary agent. Particularly preferred compounds on account of their high aphicidal activity and low mammalian toxicity are 2-dimethoxyphosphinothioylthiomethyl - 4 : 6 - diamino - s - triazine and 2 - dimethoxyphosphinothioylthiomethyl - 4 - amino - 6 - methyl - amino-s-triazine and their acid addition salts. According to the Provisional Specifications the radical NR3R4 or NR5R6 may be morpholino.
GB33358/57A 1957-10-25 1957-10-25 New phosphorus-containing organic compounds Expired GB899701A (en)

Priority Applications (28)

Application Number Priority Date Filing Date Title
BE572314D BE572314A (en) 1957-10-25
NL111238D NL111238C (en) 1957-10-25
NL103644D NL103644C (en) 1957-10-25
GB33358/57A GB899701A (en) 1957-10-25 1957-10-25 New phosphorus-containing organic compounds
DEI15546A DE1118789B (en) 1957-10-25 1958-10-23 Process for the preparation of 1, 3, 5-triazine derivatives
DEJ17863A DE1245206B (en) 1957-10-25 1958-10-23 Insect repellants
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
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
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
DEJ18006A DE1132560B (en) 1957-10-25 1960-04-22 Process for the preparation of 1, 3, 5-triazine derivatives
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
US394372A US3169904A (en) 1957-10-25 1964-08-07 Triazine derivatives possessing aphicidal properties
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
GB33358/57A GB899701A (en) 1957-10-25 1957-10-25 New phosphorus-containing organic compounds

Publications (1)

Publication Number Publication Date
GB899701A true GB899701A (en) 1962-06-27

Family

ID=10351886

Family Applications (1)

Application Number Title Priority Date Filing Date
GB33358/57A Expired GB899701A (en) 1957-10-25 1957-10-25 New phosphorus-containing organic compounds

Country Status (1)

Country Link
GB (1) GB899701A (en)

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