GB875583A - New organic phosphorus compounds and their manufacture and use - Google Patents

New organic phosphorus compounds and their manufacture and use

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Publication number
GB875583A
GB875583A GB32839/57A GB3283957A GB875583A GB 875583 A GB875583 A GB 875583A GB 32839/57 A GB32839/57 A GB 32839/57A GB 3283957 A GB3283957 A GB 3283957A GB 875583 A GB875583 A GB 875583A
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GB
United Kingdom
Prior art keywords
alkyl
formula
residue
oxygen
group
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
GB32839/57A
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.)
BASF Schweiz AG
Original Assignee
Ciba AG
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
Application filed by Ciba AG filed Critical Ciba AG
Publication of GB875583A publication Critical patent/GB875583A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
    • C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
    • C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
    • 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
    • A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
    • 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
    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/28—Titanium compounds
    • 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
    • C07F9/08—Esters of oxyacids of phosphorus
    • 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
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • 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
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/113—Esters of phosphoric acids with unsaturated acyclic alcohols
    • 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
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
    • 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
    • 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
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/2412—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of unsaturated acyclic alcohols
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/32—Esters thereof
    • C07F9/3258—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/3264—Esters with hydroxyalkyl compounds
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4075—Esters with hydroxyalkyl compounds
    • 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
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/6552—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring
    • C07F9/65522—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring condensed with carbocyclic rings or carbocyclic ring systems
    • 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
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/6574—Esters of oxyacids of phosphorus
    • C07F9/65742—Esters of oxyacids of phosphorus non-condensed with carbocyclic rings or heterocyclic rings or ring systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (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)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention comprises compounds of the formula: <FORM:0875583/IV (b)/1> in which R, R1 and R2 are alkyl, alkenyl, cycloalkyl, aralkyl, aryl, or heterocyclic residues, which may contain substituents, and of which R and R1 may together form part of a ring system, R3 is hydrogen, alkyl, or halogen atom, R4 is an alicyclic, aromatic, or heterocyclic residue with the proviso that when R4 is an unsubstituted aromatic residue and X, Y and Z simultaneously stand for oxygen, R3 must be either an alkyl residue or a halogen atom and with the further proviso that when R3 is a hydrogen atom or an alkyl residue and X, Y and Z each simultaneously stand for oxygen, no residue of an aliphatic alcohol containing at least one oxygencontaining group in the molecule additional to the hydroxyl group may be present in the molecule, X and Y are -O-, -S-, -NH or -N-R and Z is oxygen or sulphur, and n and m each represent the whole number 1 or 2, or compounds of the general formula <FORM:0875583/IV (b)/2> in which R, R1, R2, R3, X, Y, Z, n and m are as defined above. The products may have either of the given formulae or may be isomeric mixtures of compounds of the two formulae depending on the method of preparation. They may be obtained by condensing a compound of the formula <FORM:0875583/IV (b)/3> in which R5 is a C1-C4 alkyl radical and the other symbols are as defined above with a compound of the formula <FORM:0875583/IV (b)/4> in which R2, R3 and R4 are as defined abov and Hal is a halogen atom, e.g. bromine or chlorine or by reacting a compound of the formula <FORM:0875583/IV (b)/5> in which Me is an alkali metal, e.g. sodium, with a compound of the formula <FORM:0875583/IV (b)/6> Compounds in which R3 is a hydrogen atom or an alkyl group may also be obtained by the following condensation: <FORM:0875583/IV (b)/7> Reaction is generally effected by heating the reactants at raised temperature, e.g. 50-200 DEG C., and an inert solvent may be present, e.g. benzene, toluene, xylene, chlorobenzene or benzine. The reaction may be carried out in an inert gas e.g. nitrogen and/or under reduced pressure. The radicals R and R1 may be the same or different and those specified include various alkyl radicals, allyl and 2-chlorethyl and radicals containing thiocyano, cyano, or ester groups, 2- or 4-chlorophenyl, 2:4 dichlorophenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-diphenyl, and tetrahydrofuryl and the R4 radical includes phenyl, cyclohexyl, furyl, tetrahydrofuryl, chlorophenyl and nitrophenyl. Several examples are given. The products have pesticidal properties (see Group VI).ALSO:A pesticidal composition comprises in admixture with a liquid or solid diluent an organophosphorus compound of the formula <FORM:0875583/VI/1> or of the formula <FORM:0875583/VI/2> in which R, R1 and R2 are alkyl, alkenyl, cycloalkyl, aralkyl, aryl, or heterocyclic residues, which may contain substituents, and of which R and R1 may together form part of a ring system, R3 is hydrogen, alkyl, or halogen, R4 is alicyclic, aromatic or heterocyclic, with the proviso that when R4 is an unsubstituted aromatic residue and X, Y and Z each simultaneously stand for oxygen, R3 must either be an alkyl group or a halogen atom, and with the further proviso that when R3 is hydrogen or alkyl and X, Y and Z each simultaneously stand for oxygen, no residue of an aliphatic alcohol containing at least one oxygen-containing group in the molecule additional to the hydroxyl group may be present in the molecule, X and Y are -O-, -S-, -NH-, or <FORM:0875583/VI/3> Z is O or S, and n and m each represent the integer 1 or 2 (see Group IV (b)). The composition may be in the form of a dusting powder, fumigating preparation, or spraying liquor, e.g. in the form of a solution or suspension in water or an organic solvent such as ethanol, petroleum or a tar distillate and a wetting agent may be present. Specified inert fillers are kaolin, talc, chalk, sulphur, gypsum, bentonite, sulphite cellulose waste liquor, and cellulose derivatives. Other insecticides and/or fungicides may also be present. Other organic solvents specified are methanol, isopropanol, butanol, acetone, methyl ethyl ketone, methyl-cyclohexanol, benzene, toluene, xylene and kerosene.
GB32839/57A 1956-10-25 1957-10-21 New organic phosphorus compounds and their manufacture and use Expired GB875583A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH875583X 1956-10-25

Publications (1)

Publication Number Publication Date
GB875583A true GB875583A (en) 1961-08-23

Family

ID=4544366

Family Applications (1)

Application Number Title Priority Date Filing Date
GB32839/57A Expired GB875583A (en) 1956-10-25 1957-10-21 New organic phosphorus compounds and their manufacture and use

Country Status (7)

Country Link
US (1) US3035079A (en)
BE (1) BE563003A (en)
CH (1) CH353007A (en)
DE (1) DE1197271B (en)
FR (1) FR1190017A (en)
GB (1) GB875583A (en)
NL (1) NL222265A (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL111238C (en) * 1957-10-25 1900-01-01
DE1155437B (en) * 1959-04-07 1963-10-10 Dr Friedrich Cramer Process for the preparation of phospho-enolpyruvic acid dibenzyl ester
US3136690A (en) * 1959-10-12 1964-06-09 Ciba Ltd Methods and compositions for combating pests with beta-phosphate esters of -2-butenoates of mono glyceriate heterocyclic acetals and glyceriate carbonates
BE595900A (en) * 1959-10-12
DE2536977A1 (en) * 1975-08-20 1977-03-03 Bayer Ag VINYL (DI- OR TRI) THIOPHOSPHORUS (PHOSPHONE) -AEUREESTER OR. -ESTERAMIDE, METHOD OF MANUFACTURING AND USING THEY AS INSECTICIDES AND ACARICIDES

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA523521A (en) * 1956-04-03 R. Whetstone Richard Complex arylphosphonates
AT167432B (en) * 1946-10-12 1951-01-10 Bertha Braendli-Schafroth Pesticides
US2668174A (en) * 1950-08-15 1954-02-02 Celanese Corp Monopropyl dixylyl phosphate and process
US2678329A (en) * 1950-11-06 1954-05-11 Monsanto Chemicals Dialkyl monoaryl esters of orthophosphoric acid
DE974569C (en) * 1951-09-25 1961-03-02 Ciba Geigy Pest repellants
US2685552A (en) * 1952-02-29 1954-08-03 Shell Dev Dimethyl 1-carbomethoxy-1-propen-2-yl phosphate
US2766260A (en) * 1953-10-09 1956-10-09 Gen Aniline & Film Corp Methine dyestuff intermediates
US2864828A (en) * 1957-06-11 1958-12-16 Charles R Russell Esters of gamma-(tetrahydro-2-furyl) alkanols
US2894018A (en) * 1957-07-16 1959-07-07 Bayer Ag Di(lower alkyl)-mono(alpha-phenyl-beta-carbalkoxy-vinyl) phosphate esters

Also Published As

Publication number Publication date
FR1190017A (en) 1959-10-08
US3035079A (en) 1962-05-15
NL222265A (en)
CH353007A (en) 1961-03-31
DE1197271B (en) 1965-07-22
BE563003A (en)

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