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Insecticidal substituted-2,4-diaminoquinazolines

  • US 5,534,518 A
  • Filed: 06/28/1994
  • Issued: 07/09/1996
  • Est. Priority Date: 02/18/1993
  • Status: Expired due to Fees
First Claim
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1. An insecticidal composition comprising, in admixture with an agriculturally acceptable carrier, and a surface active agent, an insecticidally effective amount of a 2,4-diaminoquinazoline compound of the formula:

  • ##STR269## wherein R1 and R6 are independently hydrogen or lower alkyl;

    R2 and R7 are hydrogen, lower alkyl, alkylcarbonyl, lower alkoxycarbonyl, lower haloalkylcarbonyl, alkoxyalkylcarbonyl, alkoxyalkoxyalkylcarbonyl, alkoxyalkoxyalkoxyalkylcarbonyl, arylcarbonyl, substituted arylcarbonyl, or alkynylcarbonyl;

    or R1 and R2, taken together, form the group --R5 --O--R5, wherein R5 is lower alkylene;

    or R1 and R2, taken together, and R6 and R7 taken together each form the group ##STR270## wherein R8 and R9 are independently straight or branched chain lower alkyl;

    orR8 and R9 taken together with two to five methylene groups form an alkylene ring;

    W, Y, and Z are independently hydrogen, halogen, lower alkyl, lower alkoxy, lower haloalkyl, lower haloalkoxy, thienyl or substituted thienyl, aroyl or substituted aroyl, cyano, nitro, amino, lower dialkylamino, aryl or substituted aryl, arylalkyl, arylalkenyl, arylalkynyl, arylthio, arylsulfinyl, arylsulfonyl, arylaminoalkyl, arylalkylamino, arylalkylimino, (aryl)(halo)alkenyl, substituted (aryl)(halo)alkenyl, (aryl)(alkyl)aminoalkyl, arylalkycarbonylamino, arylalkylthio, or arylthioalkyl; and

    X is(a) hydrogen, halogen, lower alkyl, lower alkoxy, lower haloalkyl, lower haloalkoxy, thienyl or substituted thienyl, aroyl or substituted aroyl, cyano, nitro, amino, lower dialkylamino, aryl, arylalkyl, arylalkenyl, arylalkynyl, aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylaminoalkyl, arylalkylamino, arylalkylimino, (aryl)(halo)alkenyl, or substituted (aryl)(halo)alkenyl, (aryl)(alkyl)aminoalkyl, or arylalkycarbonylamino;

    or(b) substituted aryl, wherein the substituents are selected from one or more of halogens, lower alkyl, lower haloalkyl, lower alkoxy, lower alkylthio, lower alkylsulfonyl, formyl, lower alkoxycarbonyl, phenyl or phenyl substituted with one or more halogens or lower haloalkyl, phenoxy, or phenoxy substituted with one or more halogens, lower haloalkoxy, lower alkoxyalkyl, carboxy, cyano, nitro, aminocarbonyl, lower alkylcarbonylamino, lower alkylsulfonylamino;

    or substituted phenyl of the formula ##STR271## wherein R3 is hydrogen;

    alkyl, tri(lower alkyl)silylalkyl;

    (4-halophenyl)lower alkyl;

    pentahalophenylalkyl;

    pyridin-2-ylalkyl;

    or 2-(4-alkylsulfonylphenoxy)alkyl;

    or(c) substituted aryloxy, of the formula;

    ##STR272## wherein V4, W4, X4, Y4, and Z4 are selected from hydrogen, halogen, or haloalkyl;

    or(d) a benzo-fused oxygen-containing heterocycle of the formula;

    ##STR273## wherein A and B are independently selected from oxygen, methylene, and carbonyl, with the proviso that at least one of A or B is oxygen;

    D is hydrogen, halogen, lower alkyl, or lower haloalkyl; and

    E is hydrogen, hydroxy, or lower alkoxy;

    to form the corresponding heterocycle 2,3-dihydro-2,2-dimethylbenzofuran-4-yl, 2,3-dihydro-2,2-dimethylbenzofuran-7-yl, 6-halo-2,3-dihydro-2,2-dimethylbenzofuran-4-yl, 5-halo-2,3-dihydro-2,2-dimethylbenzofuran-7-yl, or 2,3-dihydro-2,2-dimethyl-3-benzofuranon-4-yl;

    or(e) an arylalkylamino of the formula;

    ##STR274## (f) an arylthioalkylcarbonylamino of the formula;

    ##STR275## and agriculturally acceptable salts thereof.

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