WHEREIN R1 AND R2 ARE EACH ALKYL OF 1 TO 4 CARBON ATOMS, AND X IS HALOGEN. PROCESSES FOR THE PRODUCTION OF THE COMPOUNDS ARE ALSO DESCRIBED. THE COMPOUNDS HAVE USEFUL HERBICDAL ACTIVITY.
Abstract:
NOVEL INSECTICIDALLY ACTIVE PHOSPHORIC ACID AMIDE ESTERS OF THE FORMULA I
R1-O-P(=O)(-NH-R2)-O-(CH3-)C=CH-COO-R3
IN WHICH EACH OF R1, R2 AND R3 REPRESENTS AN ALKYL RADICAL WITH FROM 1 TO 5 CARBON ATOMS INCLUSIVE, ARE PRODUCED BY REACTING A COMPOUND OF THE FORMULA IV
R1-O-P(=O)(-CL)2
WITH AN ALKYLAMINE IN THE PRESENCE OF AN ACID ACCEPTOR, AND THEN REACTING THE RESULTING REACTION PRODUCT WITH THE ENOL FORM OF AN ACETIC ACID ALKYL ESTER OF THE FORMULA LA III
M-O-(H3C-)C=CH-COO-R3
IN WHICH M IS A SALT FORMING AROM OR RADICAL. PREPARATIONS CONTAINING VARYING AMOUNTS OF THE COMPOUNDS OF FORMULA I AND ONE OR MORE DILUENTS (E.G. ISOC TY OCTAGLYCOL ETHER AND/OR A HIGH BOILING PETROLEUM FRACTION AND/OR XYLENE, DIISOHEXYL/HEPTYLPHENYLHEXAGLYCOL ETHER AND ACTONE, AND LAURYLHEXAGLYCOL ETHER AND SO-PROPYL ALCOHOL) ARE USED TO SHOW THE PRESTICIDAL EFFECT OF THE SAID ACTIVE AGENTS BY MEANS OF CONTACT TESTS ON BRUCHIDIUS OBTECTUS AND EPHESTIA (ANAGESTA) KEUNHIELLA, FEED EFFECT ON CARAUSIUS MOROSUS AND ACARICIDAL CONTACT EFFECT ON TETRANYCHUS TELARIUS. SOME COMPARATIVE TESTS ARE ALSO GIVEN TO DEMONSTRATE SUPERIORITY OVER KNOWN COMPOUNDS HAVING PESTICIDAL ACTIVITY, INCLUDING LESSER TOXICITY TOWARDS WARM-BLOODED ANIMALS.