Furfuryl amides of phenoxyphenoxyalkanoic acids and herbicidal use

• US 4,404,018 A
• Filed: 06/23/1982
• Issued: 09/13/1983
• Est. Priority Date: 06/23/1982
• Status: Expired due to Fees

• Current Assignee: Velsicol Chemical Corporation (Eastman Chemical Company)
• Original Assignee: Velsicol Chemical Corporation (Eastman Chemical Company)
• Inventors: Hokama, Takeo, Stach, Leonard J.
• Primary Examiner(s): Raymond, Richard
• Application Number:
  US06/391,088
• Time in Patent Office: 447 Days
• Field of Search: 71/88, 549/493
• US Class Current: 504/294
• CPC Class Codes: A01N 43/08 with oxygen as the ring hetero atom
• CPC Class Codes: C07C 205/37 the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
• CPC Class Codes: C07D 307/14 Radicals substituted by nitrogen atoms not forming part of a nitro radical
• CPC Class Codes: C07D 307/52 Radicals substituted by nitrogen atoms not forming part of a nitro radical

Abstract

This invention discloses chemical compounds of the formula ##STR1## wherein X is halogen or trifluoromethyl; Y is selected from the group consisting of hydrogen, halogen, nitro and cyano; Z is selected from the group consisting of nitro, cyano and halogen; R¹ is alkyl; R² is hydrogen or alkyl; and R³ is furfuryl or tetrahydrofurfuryl. Further discussed are herbicidal compositions utilizing the aforedescribed compounds and methods of controlling undesired vegetation therewith.

Claims

1. A compound of the formula ##STR5## wherein X is halogen or trifluoromethyl;

Y is selected from the group consisting of hydrogen, halogen, nitro and cyano;

Z is selected from the group consisting of nitro, cyano and halogen;

R¹ is alkyl;

R² is hydrogen or alkyl; and

R³ is furfuryl or tetrahydrofurfuryl.

2. The compound of claim 1, N-furfuryl-2-[3-(2-chloro-4-trifluoromethylphenoxy)-6-nitrophenoxy]propionamide.

3. The compound of claim 1, N-tetrahydrofurfuryl-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamide.

4. The compound of claim 1, N-furfuryl-2-[2-nitro-5-(2-bromo-4-trifluoromethylphenoxy)phenoxy]propionamide.

5. The compound of claim 1, N-methyl-N-furfuryl-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamide.

6. The compound of claim 1, N-ethyl-N-furfuryl-2-[2-nitro-5-(4-fluorophenoxy)phenoxy]propionamide.

7. The compound of claim 1, N-propyl-N-furfuryl-2-[2-chloro-5-(2-nitro-4-chlorophenoxy)phenoxy]propionamide.

8. The compound of claim 1, N-butyl-N-furfuryl-2-[2-bromo-5-(2-cyano-4-bromophenoxy)phenoxy]propionamide.

9. A herbicidal composition comprising an inert carrier and as the essential active ingredient, in a quantity toxic to weeds, a compound of claim 1.

10. A method of controlling weeds which comprises contacting said weeds, or the locus of said weeds, with a herbicidal composition of claim 9.