GB655875A - Improvements in or relating to pesticidal compositions - Google Patents

Improvements in or relating to pesticidal compositions

Info

Publication number
GB655875A
GB655875A GB30800/47A GB3080047A GB655875A GB 655875 A GB655875 A GB 655875A GB 30800/47 A GB30800/47 A GB 30800/47A GB 3080047 A GB3080047 A GB 3080047A GB 655875 A GB655875 A GB 655875A
Authority
GB
United Kingdom
Prior art keywords
nitrophenyl
ethyl
phosphates
thiophosphates
diphenyl
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
GB30800/47A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB655875A publication Critical patent/GB655875A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • C23F11/167—Phosphorus-containing compounds
    • C23F11/1673—Esters of phosphoric or thiophosphoric acids
    • 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
    • A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic 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
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/10—Phosphatides, e.g. lecithin
    • 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
    • C07F9/18—Esters of thiophosphoric 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
    • C07F9/20—Esters of thiophosphoric acids containing P-halide groups
    • 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
    • C07F9/242—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyaryl compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/10—Thio derivatives
    • C10M137/105—Thio derivatives not containing metal
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/041—Triaryl phosphates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/047—Thioderivatives not containing metallic elements
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/02—Groups 1 or 11
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Organic phosphates having the general formula <FORM:0655875/IV (b)/1> wherein R1 and R2 are alkyl, aralkyl or aryl groups; Z is sulphur or oxygen; Y is NH, N-alkyl, sulphur or oxygen; and X is hydrogen, halogen, alkyl, aryl, alkyloxy, aryloxy, nitro, amino, alkylamino, dialkyl amino, acyl, carboalkyloxy or carboaryloxy; are prepared by reacting an organic chlorophosphate with an alkali-forming metal nitrophenate in the presence of a solvent for the latter, as described in Specification 644,616. Typical phosphates are dimethyl-, ethyl butyl-, didecyl-, and diphenyl-4-nitrophenyl phosphates; di-ethyl-, di-(2-ethyl hexyl)-, ethyl decyl-, di-octadecyl-2-nitrophenyl phosphates; di-(2-ethyl hexyl)-4-bromo - 2 - nitrophenyl phosphate; diethyl - 4 - methyl - 2 - nitrophenyl phosphate; di-ethyl-, di-isopropyl-, dibutyl-, diamyl, di-(2-ethyl hexyl)-, dioctyl-, didecyl-, didodecyl-, dioctadecyl-, di-benzyl-, diphenyl-, N,N-bis-(ethylamido) - 4 - nitrophenyl thiophosphates; O,S - diethyl - 4 - nitrophenyl thiophosphate; diethyl-, diamyl-, di-(2-ethyl hexyl)-2,3-dinitrophenyl thiophosphates; dibutyl-, diphenyl-, dibenzyl-, 2,4-dinitrophenyl thiophosphates; di-isopropyl-, diphenyl-, dibenzyl-, 2,6-dinitrophenyl thiophosphates; diethyl 4 - chloro - 2 - nitrophenyl thiophosphate; ethyl butyl 4-methoxy - 2 - nitrophenyl phosphate; dibenzyl - 2 - methyl - 4 - nitrophenyl thiophosphate; di - (2-ethyl hexyl) - 4 - bromo - 2 - nitrophenyl phosphate; and dibutyl 4-ethoxy-2-nitrophenyl thiophosphate.ALSO:<FORM:0655875/VI/1> A pesticidal composition comprises a mixture of one or more organic phosphates and a carrier therefore, said organic phosphate having the general formula: where R1 and R2 are alkyl, aralkyl or aryl; Z is sulphur or oxygen; Y is NH, N-alkyl, S or O; X is hydrogen, halogen, alkyl, aryl, alkyloxy, aryloxy, nitro, amino, alkylamino, dialkylamino, acyl, carboalkoxy or carboaryloxy; said carrier comprising at least 50 per cent by weight of the composition and being such that if the composition is admixed with or contains water the resulting pH is not greater than 8.5. The carrier may be liquid, solid or gaseous. The liquid may be a solvent for the organic phosphate, a non-solvent, a mixture of solvent and non-solvent, the non-solvent having the further addition of an emulsifying agent such as sodium lauryl sulphate. Specified solvents are ketones, e.g. acetone, cyclohexanone, isophorone and methyl ethyl ketone; monohydric aliphatic alcohols; esters thereof, e.g. acetates, phthalates, abietates, fumarates and maleates; ether alcohols, e.g. polyethylene glycols above the trimer; ketone alcohols such as diacetone alcohol; animal and vegetable oils; polymethylated naphthalenes; aromatic hydrocarbons, e.g. benzene, toluene, xylene. The non-solvent carrier may be water, petroleum ether, kerosene, spray oils, or mixtures of such petroleum hydrocarbons. Gaseous carriers may be air, nitrogen, carbondioxide, methyl chloride and difluo-dichloromethane. Solid carriers may be clays, talcs, diatomaceous earths, Fuller's earths, pyrophyllites, cellulosic sheets and sawdust. Typical organic phosphates are dimethyl-, ethyl butyl-, didecyl- and diphenyl 4-nitrophenyl phosphates; di-ethyl-, di-(2 ethyl hexyl)-, ethyl decyl-, di-octadecyl- 2 nitrophenyl phosphates; di (2-ethyl hexyl) 4-bromo-2 nitrophenyl phosphate; diethyl 4-methyl-2-nitrophenyl phosphate; di-ethyl-, di-isopropyl-, dibutyl-, diamyl-, di (2 ethyl hexyl)-, dioctyl-, didecyl-, didodecyl-, dioctadecyl; di-benzyl-, diphenyl-, N,N-bis-(ethylamido)-4-nitrophenyl thiophosphates; O,S-diethyl 4-nitrophenyl thiophosphate; diethyl-, diamyl-, di (2 ethyl hexyl) 2, 3-dinitrophenyl thiophosphates; dibutyl-, diphenyl-, dibenzyl-2,4-dinitrophenyl thiophosphates; diisopropyl-, diphenyl-, dibenzyl-2,6-dinitrophenyl thiophosphates; di ethyl 4-chloro-2-nitrophenyl thiophosphate; ethyl butyl 4-methoxy-2-nitrophenyl phosphate; dibenzyl 2-methyl 4-nitrophenyl thiophosphate; di (2-ethyl hexyl) 4-bromo-2 nitrophenyl phosphate; dibutyl 4-ethoxy-2-nitrophenyl thiophosphate. The phosphates may be used in combination with nicotine, rotenone, pyrethrum, benzene hexachloride, D.D.T., dodecyl thiocyanate and phenothiazine; with fungicides such as sulphur, copper compounds and mercury salts; and with fertilizers. Examples of suitable compositions are given. The organic phosphate may be prepared according to Specification 644,616, [Group IV(b)]. The Specification as open to inspection under Sect. 91 comprises also the addition of lead arsenate or calcium arsenate to the composition of the invention. This subject-matter does not appear in the Specification as accepted.
GB30800/47A 1947-03-15 1947-11-20 Improvements in or relating to pesticidal compositions Expired GB655875A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US283656XA 1947-03-15 1947-03-15
US286110XA 1947-04-10 1947-04-10
US260747XA 1947-07-26 1947-07-26

Publications (1)

Publication Number Publication Date
GB655875A true GB655875A (en) 1951-08-08

Family

ID=27362691

Family Applications (2)

Application Number Title Priority Date Filing Date
GB30800/47A Expired GB655875A (en) 1947-03-15 1947-11-20 Improvements in or relating to pesticidal compositions
GB31309/47A Expired GB644616A (en) 1947-03-15 1947-11-26 Improvements in or relating to preparation of organic phosphates

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB31309/47A Expired GB644616A (en) 1947-03-15 1947-11-26 Improvements in or relating to preparation of organic phosphates

Country Status (5)

Country Link
BE (2) BE479315A (en)
CH (2) CH283656A (en)
FR (2) FR957598A (en)
GB (2) GB655875A (en)
NL (2) NL70949C (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2758954A (en) * 1952-01-04 1956-08-14 Fmc Corp Stable mixture of diethylparanitro-phenylthionophosphate and solid extender and method of making same
US2759961A (en) * 1952-07-03 1956-08-21 Howard M Fitch Amino-aryl esters of acid phosphorus compounds
US2857308A (en) * 1956-11-15 1958-10-21 Monsanto Chemicals Method of destroying nematodes employing phosphorodithioates
US2861876A (en) * 1955-12-01 1958-11-25 Monsanto Chemicals Method of destroying undesired plants
DE1116468B (en) * 1958-10-03 1961-11-02 Bayer Ag Acaricides with an ovicidal effect
US3301749A (en) * 1962-12-01 1967-01-31 Takeda Chemical Industries Ltd Pesticidal omicron, omicron-dimethyl-omicron-(2-[or 3-] methoxy-4-cyanophenyl) phosphorothioate
FR2281724A1 (en) * 1974-08-14 1976-03-12 Philagro Sa INSECTICIDE FOR SOIL TREATMENT

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE921870C (en) * 1952-05-02 1954-12-30 Bayer Ag Process for the preparation of 0, 0-dimethyl-0-4-nitro-3-chlorophenyl thiophosphate
NL255522A (en) * 1959-09-03

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2758954A (en) * 1952-01-04 1956-08-14 Fmc Corp Stable mixture of diethylparanitro-phenylthionophosphate and solid extender and method of making same
US2759961A (en) * 1952-07-03 1956-08-21 Howard M Fitch Amino-aryl esters of acid phosphorus compounds
US2861876A (en) * 1955-12-01 1958-11-25 Monsanto Chemicals Method of destroying undesired plants
US2857308A (en) * 1956-11-15 1958-10-21 Monsanto Chemicals Method of destroying nematodes employing phosphorodithioates
DE1116468B (en) * 1958-10-03 1961-11-02 Bayer Ag Acaricides with an ovicidal effect
US3301749A (en) * 1962-12-01 1967-01-31 Takeda Chemical Industries Ltd Pesticidal omicron, omicron-dimethyl-omicron-(2-[or 3-] methoxy-4-cyanophenyl) phosphorothioate
FR2281724A1 (en) * 1974-08-14 1976-03-12 Philagro Sa INSECTICIDE FOR SOIL TREATMENT

Also Published As

Publication number Publication date
BE479315A (en)
CH283656A (en) 1952-06-30
GB644616A (en) 1950-10-11
FR957803A (en) 1950-02-25
FR957598A (en) 1950-02-23
BE479314A (en)
NL75378C (en)
CH286110A (en) 1952-10-15
NL70949C (en)

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