Thiazoles and their use in controlling insects and pests

• US 4,080,457 A
• Filed: 03/15/1974
• Issued: 03/21/1978
• Est. Priority Date: 05/05/1971
• Status: Expired due to Term

• Current Assignee: Uniroyal Chemical Company Inc (Lanxess AG)
• Original Assignee: Robert E. Grahame Jr, William A. Harrison, Winchester L. Hubbard
• Inventors: Harrison, William A., Hubbard, Winchester L., Grahame, Robert E. Jr.
• Primary Examiner(s): Ore, Dale R.
• Application Number:
  US05/451,715
• Time in Patent Office: 1,467 Days
• Field of Search: 260/294.8 D, 424/266, 424/263, 424/245, 424/264
• US Class Current: 514/342
• CPC Class Codes: A01N 43/78 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• CPC Class Codes: C07D 417/04 directly linked by a ring-member-to-ring-member bond

Abstract

Certain 2-(3-pyridyl) thiazoles are useful for the control of insects, and are particularly effective against aphids. Many of these thiazoles are new compounds.

Claims

1. A method for controlling insects comprising applying to them an insecticidally effective amount of a compound of the general formula (I):

##STR47## wherein;

R², R³, R⁴ and R⁵ can be the same or different and are hydrogen or an alkyl group containing up to 3 carbon atoms, and R and R¹ can be the same or different and are;

(a) hydrogen

(b) an alkyl group containing up to 6 carbon atoms

(c) a cycloalkyl group containing 5 to 8 carbon atoms

(d) a cyano group

(e) a nitro group

(f) --R¹⁰ COXR³ wherein R¹⁰ is a single covalent bond or a divalent aliphatic acyclic hydrocarbyl group containing 1 to 3 carbon atoms, X is divalent sulfur or oxygen, and R⁶ is

(i) an alkyl, alkenyl or alkynyl group containing up to 12 carbon atoms

(ii) a cycloalkyl or cycloalkenyl group containing 5 to 8 carbon atoms

(iii) an aryl, aralkyl, alkyl substituted aralkyl, or alkaryl group containing 6 to 10 carbon atoms

(iv) an hydroxyalkyl, alkoxyalkyl, arkylaminoalkyl, or aralkylaminoalkyl group containing up to 10 carbon atoms

(g) --R¹⁰ COR⁷ where R¹⁰ has the meaning specified in (f) and wherein R⁷ is;

(i) hydrogen;

(ii) an alkyl group containing 1 to 3 carbon atoms or phenyl;

(iii) an --NR⁸ R⁹ group wherein R⁸ and R⁹ can be the same or different and are;

hydrogen, alkyl, alkenyl, alkynyl, hydroxyalkyl, alkoxyalkyl, aminoalkyl, and alkylaminoalkyl containing up to 8 carbon atoms, a cycloalkyl or cycloalkenyl of 5 to 8 carbon atoms, an aryl, haloaryl, aralkyl, and alkaryl having 6 to 10 carbon atoms.

2. The method of claim 1 wherein R², R³, R⁴ and R⁵ are hydrogen or methyl, R is:

(a) hydrogen;

(b) methyl;

(c) a cyano group;

(d) anitro group;

(e) --R¹⁰ COXR⁶ wherein R¹⁰ is a single covalent bond or methylene, X is divalent sulfur or oxygen, and R⁶ is;

(i) an alkyl, alkenyl or alkynyl group containing up to 5 carbon atoms

(ii) a cycloalkyl group having 5 to 6 carbon atoms

(iii) phenyl

(iv) an hydroxyalkyl, alkoxyalkyl, or alkylaminoalkyl group containing up to 4 carbon atoms

(f) --R¹⁰ COR⁷ wherein R¹⁰ has the meaning specified in (e) and wherein R⁷ is;

(i) hydrogen

(ii) methyl

(iii) --NR⁸ R⁹ wherein R⁸ and R⁹ can be the same or different and are hydrogen, an alkyl, alkenyl, alkynyl, hydroxyalkyl or alkoxyalkyl having up to 4 carbon atoms, an aminoalkyl or alkylaminoalkyl having no more than 5 carbon atoms wherein the sum of the carbon atoms of R⁸ and R⁹ is no greater than 6, a cycloalkyl having 5 to 6 carbon atoms, and phenyl.

3. The method of claim 1 wherein R², R³, R⁴ and R⁵ are hydrogen, R is hydrogen, methyl, ethyl, a cyano group, a nitro group or --COXR⁶ wherein X is divalent sulfur or oxygen and wherein R⁶ is:

(a) an alkyl, alkenyl, alkynyl, hydroxyalkyl, alkoxyalkyl or alkylaminoalkyl group having up to 4 carbon atoms or

(b) phenyl or cyclohexyl, or R is --CONR⁸ R⁹ wherein R⁸ and R⁹ can be the same or different and are hydrogen or an alkyl group having 1 to 3 carbon atoms, or when either R⁸ or R⁹ is hydrogen, the other group is an hydroxyalkyl having up to 2 carbon atoms, an alkoxyalkyl having 1 to 4 carbon atoms, alkylaminoalkyl having 1 to 5 carbon atoms or a cyclohexyl radical.

4. The method of claim 3 wherein said compound is 4-methyl-2-(3-pyridyl)thiazole.

5. The method of claim 3 wherein said compound is 4-ethyl-2-(3-pyridyl)thiazole.

6. The method of claim 3 wherein said compound is 4,5-dimethyl-2-(3-pyridyl)thiazole.

7. The method of claim 3 wherein said compound is 4-methyl-5-nitro-2-(3-pyridyl)thiazole.

8. The method of claim 3 wherein said compound is the HCl salt of 4-ethyl-5-nitro-2-(3-pyridyl)thiazole.

9. The method of claim 3 wherein said compound is ethyl-4-methyl-2-(3-pyridyl)-5-thiazolecarboxylate.

10. The method of claim 3 wherein said compound is N,4-dimethyl-2-(3-pyridyl)-5-thiazolecarboxamide.

11. The method of claim 3 wherein said compound is N-ethyl-4-methyl-2-(3-pyridyl)-5-thiazolecarboxamide.

12. The method of claim 3 wherein said compound is N,N,4-trimethyl-2-(3-pyridyl)-5-thiazolecarboxamide.

13. The method of claim 3 wherein said compound is N,N-diethyl-4-methyl-2-(3-pyridyl)-5-thiazolecarboxamide.

14. The method of claim 3 wherein said compound is ethyl 2-(3-pyridyl)-4-thiazoleacetate.