N-Phenyl-N-methyl-urea derivatives, and their production and use

• US 4,249,938 A
• Filed: 06/27/1978
• Issued: 02/10/1981
• Est. Priority Date: 06/28/1977
• Status: Expired due to Term

• Current Assignee: Sumitomo Chemical Company Limited
• Original Assignee: Sumitomo Chemical Company Limited
• Inventors: Takemoto, Ichiki, Yoshida, Ryo, Kamoshita, Katsuzo, Sumida, Seizo
• Primary Examiner(s): Hollrah, Glennon H.
• Application Number:
  US05/919,683
• Time in Patent Office: 959 Days
• Field of Search: 71/120, 71/98, 260/453 RW
• US Class Current: 504/332
• CPC Class Codes: A01N 47/30 Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
• CPC Class Codes: C07C 275/34 having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
• CPC Class Codes: C07C 275/64 having nitrogen atoms of urea groups singly-bound to oxygen atoms
• CPC Class Codes: C07C 323/44 X or Y being nitrogen atoms

Abstract

An N'"'"'-phenyl-N-methyl-urea derivative of the formula: ##STR1## wherein R¹, R² and R³ are each hydrogen, lower alkyl, lower alkoxy, lower alkylthio, halogen or trifluoromethyl, R⁴ is hydrogen or lower alkyl, A is methyl or methoxy, X is oxygen or sulfur, Y is hydrogen or halogen, Z is a straight or branched alkylene chain having not more than 8 carbon atoms which may have no less than one atom of oxygen and/or sulfur inside and/or at the end of the alkylene chain and n is an integer of 1 to 3, which shows a pronounced herbicidal activity against a wide variety of weeds in the cultivation of crop plants without any material toxicity to mammals or fish or any chemical injury to said crop plants.

Claims

1. A compound of the formula:

##STR160## wherein R¹, R² and R³ are each hydrogen, lower alkyl, lower alkoxy, lower alkylthio, halogen or trifluoromethyl, R⁴ is hydrogen or lower alkyl, Y is hydrogen or halogen, Z is a straight or branched alkylene chain of not more than 8 carbon atoms or an alkylene chain of not more than 8 carbon atoms having one or two atoms of oxygen and/or sulfur inside and/or at the end thereof, and n is an integer of 1 to 3, with the following provisos;

(a) when R¹ is lower alkyl or lower alkoxy, R² is hydrogen or methyl, R⁴ is hydrogen, Y is hydrogen and Z is methylene, R³ is lower alkyl, lower alkoxy, halogen or trifluoromethyl;

(b) when R¹ is hydrogen, halogen or trifluoromethyl, R⁴ is hydrogen, Y is hydrogen and Z is methylene, R² and R³ are each hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl;

(c) when R⁴ is hydrogen, Y is halogen and Z is methylene, R¹, R² and R³ are each hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl;

(d) when R⁴ is hydrogen, Z is a straight or branched alkylene chain of 2 to 8 carbon atoms or a straight or branched alkylene chain of 1 to 7 carbon atoms having one or two atoms of oxygen and/or sulfur inside and/or at the end thereof; and

(e) when R⁴ is lower alkyl, Z is a straight or branched alkylene chain of 1 to 8 carbon atoms or a straight or branched chain of 1 to 7 carbon atoms having one or two atoms of oxygen and/or sulfur inside and/or at the end thereof.

2. The compound according to claim 1, wherein R¹, R² and R³ are each hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, R⁴ is hydrogen, Y is hydrogen and Z is methylene, provided that when R¹ is lower alkyl or lower alkoxy and R² is hydrogen or methyl, R³ is lower alkyl, lower alkoxy, halogen or trifluoromethyl.

3. The compound according to claim 2, wherein no less than one of R¹, R² and R³ is halogen.

4. The compound according to claim 2, wherein R¹ is hydrogen, R² is hydrogen and R³ is lower alkyl or lower alkoxy.

5. The compound according to claim 2, which is N'"'"'-4-[2-(2-methylphenyl)ethoxy]phenyl-N-methoxy-N-methylurea.

6. The compound according to claim 1, wherein R¹, R² and R³ are each hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, R⁴ is hydrogen, Y is halogen and Z is methylene.

7. The compound according to claim 6, which is N'"'"'-3-chloro-4-[2-(4-methylphenyl)ethoxy]phenyl-N-methoxy-N-methylurea.

8. The compound according to claim 6, which is N'"'"'-3-chloro-4-[2-(4-isopropylphenyl)ethoxy]phenyl-N-methoxy-N-methylurea.

9. The compound according to claim 1, wherein Z is a straight or branched alkylene chain of not more than 8 carbon atoms and Y is halogen.

10. The compound according to claim 1, which is N'"'"'-4-(3-phenylpropoxy)phenyl-N-methoxy-N-methylurea.

11. A herbicidal composition comprising as an active ingredient a herbicidally effective amount of at least one of the compounds according to claim 1, and an inert carrier.

12. The composition according to claim 11, wherein the concentration of the active ingredient is from about 1 to 80% by weight.

13. A method for controlling weeds which comprises applying a herbicidally effective amount of the compound according to claim 1 to the area where the weeds grow.

14. A method of selectively combating weeds in the cultivation of soybeans, cotton, corn, wheat or rice, which comprises applying a herbicidally effective amount of the compound according to claim 1 to the area where the soybean, corn, cotton, wheat or rice crop is cultivated.