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

• Current Assignee: FMC Corporation
• Original Assignee: FMC Corporation
• Inventors: Yeager, Walter H., Fiordeliso, James J., Ray, Partha S., Cullen, Thomas G., Henrie, Robert N. II, Silverman, Ian R., Dixson, John A., Peake, Clinton J., Buser, John W., Chaguturu, Munirathnam K., Lew, Albert C.
• Primary Examiner(s): Shah, Mukund J.
• Assistant Examiner(s): Grumbling, Matthew V.
• Application Number:
  US08/267,340
• Time in Patent Office: 742 Days
• Field of Search: 544/284, 544/291, 514/260
• US Class Current: 514/266.4
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 55/00 Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing organo-phosphorus compounds A01N57/00
• CPC Class Codes: C07D 239/95 with hetero atoms directly attached in positions 2 and 4
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 405/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 409/04 directly linked by a ring-member-to-ring-member bond

Abstract

An insecticidal composition comprising, in admixture with an agriculturally acceptable carrier, an insecticidally effective amount of a 2,4-diaminoquinazoline compound of the formula: ##STR1## wherein R¹, R², R⁶, R⁷, W, X, Y, and Z are as defined herein; methods of using the same; novel 2,4-diaminoquinazolines per se; and intermediates in the preparation thereof.

Claims

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;

or

R⁸ 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.

2. The composition of claim 1 wherein R¹ is hydrogen or lower alkyl, and R⁶ is hydrogen.

3. The composition of claim 1 where R¹, R², R⁶, and R⁷ are hydrogen.

4. The composition of claim 1 wherein Y and Z are hydrogen.

5. The composition of claim 1 wherein W is halogen or lower alkyl.

6. The composition of claim 1 wherein X is phenyl or substituted phenyl.

7. The composition of claim 1 wherein X is aroyl or substituted aroyl of the formula:

##STR276## wherein V², W², X², Y², and Z² are independently selected from hydrogen, halogen, haloalkyl, cyano, carboxy, lower alkoxycarbonyl, and phenyl substituted with halogen or lower haloalkyl.

8. The composition of claim 1 wherein X is (aryl)(halo)alkenyl of the formula:

##STR277## wherein V¹, W¹, X¹, Y¹, and Z¹ are independently selected from hydrogen, halogen, lower alkyl, lower haloalkyl, cyano, carboxy, lower alkoxycarbonyl, and aminocarbonyl.

9. The composition of claim 1 wherein X is a benzo-fused oxygen-containing heterocycle of the formula:

##STR278## 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.

10. The composition of claim 1 wherein

R² and R⁷ are independently hydrogen, lower alkyl, alkylcarbonyl, lower alkoxycarbonyl, lower haloalkylcarbonyl, alkoxyalkylcarbonyl, alkoxyalkoxyalkylcarbonyl, or alkoxyalkoxyalkoxyalkylcarbonyl.

11. The composition of claim 1 wherein

R¹ is hydrogen, or lower alkyl;

R⁶ is hydrogen;

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

Y and Z are hydrogen;

W is halogen, or lower alkyl; and

X is phenyl, or 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 ##STR279## wherein R³ is hydrogen;

alkyl;

tri(lower alkyl)silylalkyl;

(4-halophenyl)lower alkyl;

pentahalophenylalkyl;

pyridin-2-ylalkyl;

or 2-(4-alkylsulfonylphenoxy)alkyl.

12. The composition of claim 1 wherein

R¹ is hydrogen, or lower alkyl;

R⁶ is hydrogen;

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

Y and Z are hydrogen;

W is halogen, or lower alkyl; and

X is aroyl, or substituted aroyl of the formula;

##STR280## wherein V², W², X², Y², and Z² are independently selected from hydrogen, halogen, haloalkyl, cyano, carboxy, lower alkoxycarbonyl, and phenyl substituted with halogen or lower haloalkyl.

13. The composition of claim 1 wherein

R¹ is hydrogen, or lower alkyl;

R⁶ is hydrogen;

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

Y and Z are hydrogen;

W is halogen or lower alkyl; and

X is (aryl)(halo)alkenyl of the formula;

##STR281## wherein V¹, W¹, X¹, Y¹, and Z¹ are independently selected from hydrogen, halogen, lower alkyl, lower haloalkyl, cyano, carboxy, lower alkoxycarbonyl, and aminocarbonyl.

14. The composition of claim 1 wherein

R¹ is hydrogen, or lower alkyl;

R⁶ is hydrogen;

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

Y and Z are hydrogen;

W is halogen or lower alkyl (e.g., methyl); and

X is a benzo-fused oxygen-containing heterocycle of the formula;

##STR282## 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.

15. The composition of claim 1 wherein

R¹, R², R⁶, and R⁷ are hydrogen;

Y and Z are hydrogen;

W is hydrogen, halogen, or lower alkyl;

X is arylaminoalkyl or arylalkylimino of the formula;

##STR283## wherein Q is alkylimino of the formula --N═

CH--, or aminoalkyl of the formula --CH₂ NH--;

n is 1, 2, or 3;

m is 0 or 1; and

R⁴ is hydrogen or lower alkyl;

with the proviso that when m is 0, R⁴ must be hydrogen, and n must be 1.

16. The composition of claim 1 wherein

R¹, R², R⁶, and R⁷ are hydrogen;

W, Y, and Z are hydrogen; and

X is an (aryl)(alkyl)aminoalkyl of the formula;

##STR284##

17. A method for controlling insects which comprises applying to the locus where control is desired an insecticidal amount of the composition of claim 15.

18. A method for controlling insects which comprises applying to the locus where control is desired an insecticidal amount of the composition of claim 16.

19. A method for controlling insects which comprises applying to the locus where control is desired an insecticidal amount of the composition of claim 1.

20. A method for controlling insects which comprises applying to the locus where control is desired an insecticidal amount of the composition of claim 2.

21. A method for controlling insects which comprises applying to the locus where control is desired an insecticidal amount of the composition of claim 3.

22. A method for controlling insects which comprises applying to the locus where control is desired an insecticidal amount of the composition of claim 4.

23. A method for controlling insects which comprises applying to the locus where control is desired an insecticidal amount of the composition of claim 5.

24. A method for controlling insects which comprises applying to the locus where control is desired an insecticidal amount of the composition of claim 6.

25. A method for controlling insects which comprises applying to the locus where control is desired an insecticidal amount of the composition of claim 7.

26. A method for controlling insects which comprises applying to the locus where control is desired an insecticidal amount of the composition of claim 8.

27. A method for controlling insects which comprises applying to the locus where control is desired an insecticidal amount of the composition of claim 9.

28. A method for controlling insects which comprises applying to the locus where control is desired an insecticidal amount of the composition of claim 10.

29. A method for controlling insects which comprises applying to the locus where control is desired an insecticidal amount of the composition of claim 11.

30. A method for controlling insects which comprises applying to the locus where control is desired an insecticidal amount of the composition of claim 12.

31. A method for controlling insects which comprises applying to the locus where control is desired an insecticidal amount of the composition of claim 13.

32. A method for controlling insects which comprises applying to the locus where control is desired an insecticidal amount of the composition of claim 14.