GB781471A - Pest control agents - Google Patents

Pest control agents

Info

Publication number
GB781471A
GB781471A GB15917/54A GB1591754A GB781471A GB 781471 A GB781471 A GB 781471A GB 15917/54 A GB15917/54 A GB 15917/54A GB 1591754 A GB1591754 A GB 1591754A GB 781471 A GB781471 A GB 781471A
Authority
GB
United Kingdom
Prior art keywords
ethyl
alk
morpholino
nr3r4
ethylene
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
GB15917/54A
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.)
Sandoz AG
Original Assignee
Sandoz 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 Sandoz AG filed Critical Sandoz AG
Publication of GB781471A publication Critical patent/GB781471A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02Phosphorus compounds
    • C07F9/06Phosphorus compounds without P—C bonds
    • C07F9/16Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165Esters of thiophosphoric acids
    • C07F9/1651Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl

Abstract

The invention comprises thiophosphoric esters of the formula <FORM:0781471/IV (a)/1> where R1 and R2 are C1-C4 alkyl, R3 and R4 are C1-C4 alkyl or together with the N atom form a saturated heterocyclic ring, alk is an ethylene residue which may be substituted and Y1 and Y2 are O or S at least one being S; water-soluble salts are included. These are made by reacting <FORM:0781471/IV (a)/2> with <FORM:0781471/IV (a)/3> where one X is halogen and the other is the Y2 cation. When the reactants are a phosphoric or thiophosphoric diester halide and an aminoalcoholate there is preferably used benzene, toluene or an excess of Y2OH as solvent. When the latter reactant is a haloalkylamine the solvent is preferably water, acetone or benzene. Examples show the preparation of the following compounds: (1) R1 = R2 = R3 = R4 = ethyl, Y1 = S, Y2 = O, alk=ethylene; (2) R1 = R2 ethyl, R3 = R4 = methyl, Y1 = S, T2=O, alk ethylene; (3) R1=R2=ethyl, NR3R4 = morpholino, Y1=S, Y2=O, alk=ethylene; (4) R1= R2=ethyl, NR3R4=morpholino, Y1=S, Y2 O, alk=propylene; (5) R1=R2=ethyl, NR3R4=morpholino, Y1=O, Y2=S, alk= ethylene, and its hydrochloride, sulphate, acetate and methanesulphonate; (6) R1=R2= ethyl, NR3R4=morpholino, Y1=Y2=S, alk= ethylene, and its hydrochloride and methanesulphonate; (7) R1=R2=R3=R4=ethyl, Y1\t =O, Y2=S, alk=ethylene; (8) R1=R2=ethyl, R3=R4=isopropyl, Y1=S, Y2=O, alk=ethylene; (9) R1=R2=methyl, NR3R4=morpholino, Y1=Y2=S, alk=ethylene, and hydrochloride and methanesulphonate; (10)R1=R2= methyl, NR3R4=morpholino, Y1=O, Y2=S, alk=ethylene, and hydrochloride; (11) R1= R2=methyl, NR3R4=morpholino, Y1=S, Y2=O, alk=ethylene and hydrochloride; (12) R1= R2=ethyl, NR3R4=morpholino, Y1=S, Y2 O, alk=isopropoxypropylene; (13) R1=R2= ethyl, NR3R4=morpholino, Y1=S, Y2=O, alk=methoxypropylene; (14) R1=R2=ethyl, NR3R4=morpholino, Y1=Y2=S, alk=methoxypropylene, and hydrochloride; (15) R1= R2=methyl, NR3R4=morpholino, Y1=Y2= S, alk=methoxypropylene, and hydrochloride; (16) R1=R2=ethyl, NR3R4=morpholino, Y1=Y2=S, alk=ethoxypropylene; (17) R1=R2= ethyl, R3=R4=methyl, Y1=S, Y2=O, alk= methoxypropylene, and its hydrochloride. The following tertiary amino alcohols are made from the appropriate secondary amines and glycidol ethers: 1-alkoxy-3-morpholino-propan-2-ols, where the alkyl group is methyl, ethyl or isopropyl, and 1-methoxy-3-dimethylamino-propan-2-ol. 2 - Chloro - 1 - methoxy - 3 - morpholino - propane and 2 - chloro - 1 - ethoxy - 3 - morpholinopropane are prepared from the corresponding alcohols and thionyl chloride. Reference has been directed by the Comptroller to Specifications 738,839 and 740,563.ALSO:Insecticidal compositions contain as essential ingredient a basic thiophosphoric ester of the formula <FORM:0781471/VI/1> (or salt thereof) where R1 and R2 are C1 -C4 alkyl, R3 and R4 are C1-C4 alkyl or together with the N atom form a saturated hererocyclic ring, alk is an ethylene residue which may be substituted and Y1 and Y2 are O or S, at least one being S. The esters are active as contact and systemic insecticides when applied to plants from aqueous solutions or emulsions. They may be emulsified with the aid of polyglycol ethers or thioethers, together with liquids such as alcohols or hydrocarbons, or solids such as talcum, kaolin, kieselguhr or bentonite. The esters may also be used in the solid form with the above carriers and also adhesive and wetting agents if desired. Examples of suitable compositions are (1) aqueous solutions of O:O - diethyl - S - (b - morpholino - ethyl) monothiophosphate and its hydrochloride, sulphate, acetate and methanesulphonate, O:O-diethyl - O - (b - diethylaminoethyl) monothiophosphate, O:O - diethyl - S - (b - morpholinoethyl) dithiophosphate methanesulphonate, O:O - dimethyl - O - (b - morpholino - ethyl) monothiophosphate hydrochloride and O:O-dimethyl - S - (b - morpholino - ethyl) dithiophosphate hydrochloride; (2) aqueous dispersions of O:O-diethyl-O-(b -morpholino-ethyl) monothiophosphate and O:O - diethyl - S-(b - morpholino - ethyl) dithiophosphate, using p - iso - octylphenyl octaglycol ether as emulsifier; and (3) a dusting agent comprising O:O - diethyl - O - (b - dimethylamino - ethyl) monothiophosphate and talcum. Other suitable esters are mentioned. Reference has been directed by the Comptroller to Specifications 738,839, [Group IV (b)], and 740,563.
GB15917/54A 1953-05-29 1954-05-28 Pest control agents Expired GB781471A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH781471X 1953-05-29

Publications (1)

Publication Number Publication Date
GB781471A true GB781471A (en) 1957-08-21

Family

ID=4536252

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15917/54A Expired GB781471A (en) 1953-05-29 1954-05-28 Pest control agents

Country Status (1)

Country Link
GB (1) GB781471A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1125929B (en) * 1958-12-30 1962-03-22 Albert Ag Chem Werke Process for the preparation of thio- or dithiophosphoric acid esters

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1125929B (en) * 1958-12-30 1962-03-22 Albert Ag Chem Werke Process for the preparation of thio- or dithiophosphoric acid esters

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