GB808853A - Process for preparing amidic esters of di-thiophosphoric acids, and insecticidal compositions including said derivatives - Google Patents

Process for preparing amidic esters of di-thiophosphoric acids, and insecticidal compositions including said derivatives

Info

Publication number
GB808853A
GB808853A GB8095/56A GB809556A GB808853A GB 808853 A GB808853 A GB 808853A GB 8095/56 A GB8095/56 A GB 8095/56A GB 809556 A GB809556 A GB 809556A GB 808853 A GB808853 A GB 808853A
Authority
GB
United Kingdom
Prior art keywords
2pssch
group
compound
c2h5o
propyl
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
GB8095/56A
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.)
Montedison SpA
Original Assignee
Montedison SpA
Montecatini Societa Generale per lIndustria Mineraria e Chimica SpA
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 Montedison SpA, Montecatini Societa Generale per lIndustria Mineraria e Chimica SpA filed Critical Montedison SpA
Publication of GB808853A publication Critical patent/GB808853A/en
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
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C07F9/1653—Esters of thiophosphoric acids with arylalkanols
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • 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
    • C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl

Abstract

An amidic ester of dithiophosphoric acid having the general formula: <FORM:0808853/IV (b)/1> wherein R1 is an alkyl group (e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, or isobutyl) or an aryl group, R2 is a substituted or unsubstituted alkyl or aryl group (e.g. a methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, phenyl, chlorophenyl, or nitrophenyl group), R3 and R4 are the same or different and represent hydrogen or an alkyl group (such as a methyl, ethyl, n-propyl or isopropyl group) is obtained by treating a dithiophosphate of the general formula: <FORM:0808853/IV (b)/2> wherein Y is an alkali metal, an alkaline earth metal, or the ammonium radical and R1 is as defined above with an amide of an halogen substituted alkyl- or aryl-acetic acid of the general formula: <FORM:0808853/IV (b)/3> wherein X is halogen (Cl, Br or I) and R2, R3 and R4 are as defined above, preferably in the presence of a solvent for one or both of the reactants. Alternatively, the free dithiophosphoric acid ester, i.e. a compound of the above general formula in which Y is H, may be used in conjunction with a basic compound of a metal which is sufficiently basic to neutralize the acid, e.g. Na2CO3, NaHCO3, K2CO3 KHCO3, or NaOH. In this case the dithiophosphate salt is formed in situ. Specified solvents which may be used are water, alcohols, ethers, ketones, esters, dioxane, and aromatic hydrocarbons. Examples are given for the production of compounds of the formula: (1) (C2H5O)2PSSCH(CH3)CONHisoC3H7; (2) <FORM:0808853/IV (b)/4> ; (3) <FORM:0808853/IV (b)/5> ; (4) <FORM:0808853/IV (b)/6> ; (5) (CH3O)2 PSSCH(CH3)CONHisoC3H7; (6) (CH3O)2 PSSCH(CH3)CONHC2H5; (7) (C2H5O)2PSSCH (CH3)CONHC2H5; (8) (C2H5O)2PSSCH(CH3) CONH2; (9) (C2H5O)2PSSCH(C2H5)CONHC2 H5; (10) (isoC3H-O)2PSSCH(C2H5)CONHC2H5 (11) (CH3O)2PSSCH(C6H5)CONHC2H5; and (12) <FORM:0808853/IV (b)/7> The invention includes each of these compounds as new products. The products have pesticidal properties and may be used in pesticidal compositions (see Group VI).ALSO:A pesticidal composition comprises an inert diluent and an amidic dithiophosphate ester or mixture of such amidic dithiophosphate esters having the formula <FORM:0808853/VI/1> wherein R1 is an alkyl group or an aryl group, R2 is a substituted or unsubstituted alkyl or aryl group, and R3 and R4 are the same or different and represent hydrogen or an alkyl group such as methyl, ethyl, n-propyl or isopropyl (see Group IV (b)). The composition may also include one or more known pesticidal agents such as insecticides and/or fungicides and may also include one or more plant feeding substances and/or fertilizers. Specified compositions are acetone and benzene solutions of a compound of the formula (C2H5O)2PSSCH(CH3)CONHisoC3H7, and aqueous dispersions of the same compound. Reference is also made to solutions of the same compound and of a compound of the formula (CH3O)2PSSCH(C6H5)CONHisoC3H7 in dimethylacetamide. When R1 and R2 are alkyl radicals they may be methyl, ethyl, n-propyl, isopropyl, n-butyl, or isobutyl and R2 may also be phenyl, chlorophenyl, or nitrophenyl.
GB8095/56A 1955-03-25 1956-03-15 Process for preparing amidic esters of di-thiophosphoric acids, and insecticidal compositions including said derivatives Expired GB808853A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT345334X 1955-03-25

Publications (1)

Publication Number Publication Date
GB808853A true GB808853A (en) 1959-02-11

Family

ID=11239682

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8095/56A Expired GB808853A (en) 1955-03-25 1956-03-15 Process for preparing amidic esters of di-thiophosphoric acids, and insecticidal compositions including said derivatives

Country Status (6)

Country Link
BE (1) BE546421A (en)
CH (1) CH345334A (en)
FR (1) FR1148927A (en)
GB (1) GB808853A (en)
LU (1) LU34267A1 (en)
NL (2) NL95145C (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2959608A (en) * 1959-01-30 1960-11-08 Fisons Pest Control Ltd Chemical process for making omicron, omicron-dialkyl-5-carbamoylmethyl-phosphorodithioates
EP0083123A1 (en) * 1981-12-29 1983-07-06 The Procter & Gamble Company Alphaphoshato amide compounds and lubricant and hydrocarbon fuel compositions containing them
CN113637514A (en) * 2013-12-06 2021-11-12 巴斯夫欧洲公司 Composition and method of forming the same

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2959608A (en) * 1959-01-30 1960-11-08 Fisons Pest Control Ltd Chemical process for making omicron, omicron-dialkyl-5-carbamoylmethyl-phosphorodithioates
EP0083123A1 (en) * 1981-12-29 1983-07-06 The Procter & Gamble Company Alphaphoshato amide compounds and lubricant and hydrocarbon fuel compositions containing them
CN113637514A (en) * 2013-12-06 2021-11-12 巴斯夫欧洲公司 Composition and method of forming the same

Also Published As

Publication number Publication date
NL205701A (en)
NL95145C (en)
LU34267A1 (en)
BE546421A (en)
CH345334A (en) 1960-03-31
FR1148927A (en) 1957-12-18

Similar Documents

Publication Publication Date Title
ES250753A1 (en) Process for the preparation of o,o-dialkyl-dithiophosphoryl-fatty acid compounds and pesticidal compositions containing the same
GB906982A (en) Thiophosphoric acid esters
US2901481A (en) Process for preparing dialkyldithiophosphoric acid ester derivatives having two amide groups in the molecule and the insecticidal compounds obtained thereby
GB1129797A (en) Phosphorus-containing pyrimidine derivatives and biologically active compositions containing them
GB808853A (en) Process for preparing amidic esters of di-thiophosphoric acids, and insecticidal compositions including said derivatives
US3040046A (en) Quinoxalines and processes for their production
GB916704A (en) Dithiophosphoric acid esters
GB1564182A (en) Benzothiazolone and benzoxazolone derivatives
GB1275694A (en) Thiazolo-(thiono)phosphoric(phosphonic)acid esters, process for their preparation, and their use as insecticides, acaricides and fungicides
US3454681A (en) Amido phosphorus-containing esters
US3053847A (en) Phosphorus compounds and processes for their production
US3202658A (en) Thionophosphonic acid esters and a process for their production
US3243437A (en) Pyrimidine phosphorothioates
US2777792A (en) Pest combating agents
GB834814A (en) ª‡-substituted o, o-dialkyl-dithiophosphorylacetic esters and process for their preparation
GB1007331A (en) Quinazolin-3-oxides and benzo-1,2,3-triazine-3-oxides
GB847550A (en) Phosphonic acid esters
GB744360A (en) Manufacture of organic compounds containing halogen and phosphorus
US3732343A (en) 1-halo-2-aryloxy-vinyl (2)-phosphates
GB1313247A (en) Thiono- phosphoric -phosphonic- acid esters a process for their preparation and their use as insecticides and acaricides
US2870187A (en) O, o-dimethyl-o-(4-chloro-3-nitrophenyl)-thiophosphoric acid esters and their preparation
GB932659A (en) Thiophosphorus acid ester derivatives of diacetamides
US3705930A (en) Trithiolphosphoric acid esters
GB970581A (en) New insecticidal thiophosphoric acid esters and their manufacture
GB1085340A (en) New phosphoric and thiophosphoric acid ester derivatives