Intermediates to prepare herbicidal pyrimidone derivatives

Patent metadata

Field	Value
Publication number	US-9630928-B2
Application number	US-201514870113-A
Country	US
Kind code	B2
Filing date	Sep 30, 2015
Priority date	Sep 9, 2009
Publication date	Apr 25, 2017
Grant date	Apr 25, 2017

Abstract

Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof,

X is CH or N;
Y is C(O) or S(O) 2 ; provided that when Y is S(O) 2 , then X is CH;
A is a radical selected from the group consisting of

and B 1 , B 2 , B 3 , T, R 1 , R 2 R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.

First claim

What is claimed is:

1. A compound of Formula 1R including all stereoisomers, N-oxides, and salts thereof:

wherein
R 1 is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl, 4-ethylphenyl, 2-methylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 2,3-dimethylphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl; or n-Pr, i-Pr, n-Bu, c-hexyl, —CH 2 CH 2 OCH 3 , —CH 2 CH 2 CH 2 OCH 3 or —CH 2 CH 2 OCH 2 CH 3 ;
R 2 is phenyl or —W 3 (phenyl), each substituted on ring members with up to two substituents selected from R 21 ; or -G or; or C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl;
each G is independently a 5- or 6-membered heterocyclic ring or an 8-, 9- or 10-membered fused bicyclic ring system, each ring or ring system optionally substituted with up to five substituents selected from R 21 on carbon ring members and R 22 on nitrogen ring members;
each R 21 is independently halogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH 2 , —C(═S)NH 2 , —C(═O)NHCN, —C(═O)NHOH, —SH, —SO 2 NH 2 , —SO 2 NHCN, —SO 2 NHOH, —OCN, —SCN, —SF 5 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 5 cyanoalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 8 alkoxyalkoxy, C 2 -C 8 alkylcarbonyloxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 1 -C 6 alkylamino, C 2 -C 8 dialkylamino, C 1 -C 6 haloalkylamino, C 2 -C 8 halodialkylamino or C 3 -C 8 cycloalkylamino; and
each R 22 is independently C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl or C 2 -C 8 alkoxyalkyl.

2. A compound of claim 1 wherein
R 2 is 3-thienyl or 2-thienyl.

3. A compound of claim 1 wherein
R 2 is n-propyl, n-butyl, or cyclopropyl.

4. A compound of the formula

5. A compound of the formula

Assignees

• Du Pont
• Du Pont

Inventors

• Selby Thomas Paul
• Smith Brenton Todd
• Taggi Andrew Edmund

Classifications

• C07D405/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• A01N43/78

  1,3-Thiazoles; Hydrogenated 1,3-thiazoles · CPC title

• C07D401/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D409/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D413/04

  directly linked by a ring-member-to-ring-member bond · CPC title