Herbicidal substituted pyrimidinyloxy benzene compounds

Patent metadata

Field	Value
Publication number	US-9695155-B2
Application number	US-201415101095-A
Country	US
Kind code	B2
Filing date	Dec 9, 2014
Priority date	Dec 10, 2013
Publication date	Jul 4, 2017
Grant date	Jul 4, 2017

Abstract

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

wherein each Y 1 , Y 2 , Y 3 , Y 4 , Z, R 2 , m and R 3 are as defined in the disclosure.

Also disclosed are compositions containing a compound 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 selected from a compound of Formula 1, N-oxides and salts thereof

wherein
each Y 1 , Y 2 , Y 3 and Y 4 is independently selected from the group consisting of N and CR 1 , provided no more than 3 of Y 1 , Y 2 , Y 3 and Y 4 are N;
Z is selected from the group consisting of O and S;
each R 1 is independently selected from the group consisting of hydrogen, halogen, cyano, nitro, SF 5 , CHO, C(═O)NH 2 , C(═S)NH 2 , SO 2 NH 2 , C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 4 -C 8 alkylcycloalkyl, C 4 -C 8 cycloalkylalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 3 -C 7 cycloalkylcarbonyl, C 2 -C 8 alkylaminocarbonyl, C 3 -C 10 dialkylaminocarbonyl, C 1 -C 4 alkoxy, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, C 1 -C 4 haloalkoxy, C 3 -C 4 haloalkenyloxy, C 3 -C 4 haloalkynyloxy, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 4 -C 8 cycloalkylalkoxy, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 2 -C 6 alkoxyhaloalkyl, C 2 -C 6 alkoxyalkoxy, C 2 -C 4 alkylcarbonyloxy, C 2 -C 6 cyanoalkyl, C 2 -C 6 cyanoalkoxy, C 2 -C 4 alkylthioalkyl, SO n R 1A , Si(CH 3 ) 3 , B(—OC(R 1B ) 2 C(R 1B ) 2 O—); a phenyl ring optionally substituted with up to 5 substituents independently selected from R 1C ; and a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from the group consisting of up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R 1C on carbon atom ring members and R 1D on nitrogen atom ring members;
R 2 is selected from the group consisting of halogen, cyano, nitro, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, SO n R 2A , C 1 -C 4 haloalkyl and C 3 -C 6 cycloalkyl;
m is selected from the group consisting of 0, 1, 2 and 3;
each R 3 is independently selected from the group consisting of halogen, cyano, hydroxy, nitro, amino, CHO, C(═O)NH 2 , C(═S)NH 2 , SO 2 NH 2 , C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 4 -C 8 alkylcycloalkyl, C 4 -C 8 cycloalkylalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 3 -C 7 cycloalkylcarbonyl, C 1 -C 4 alkoxy, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, C 1 -C 4 haloalkoxy, C 3 -C 4 haloalkenyloxy, C 3 -C 4 haloalkynyloxy, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 4 -C 8 cycloalkylalkoxy, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 2 -C 6 alkoxyhaloalkyl, C 2 -C 6 alkoxyalkoxy, C 2 -C 4 alkylcarbonyloxy, C 2 -C 6 cyanoalkyl, C 2 -C 6 cyanoalkoxy, C 2 -C 4 alkylthioalkyl, Si(CH 3 ) 3 , C≡CSi(CH 3 ) 3 , C(═O)N(R 3A )(R 3B ), C(═NOR 3C )H, C(═NR 3D )H, SO n R 3E ; a phenyl ring optionally substituted with up to 5 substituents independently selected from R 3F ; a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from the group consisting of up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R 3F on carbon atom ring members and R 3G on nitrogen atom ring members; and pyrimidinyloxy;
each n is independently selected from the group consisting of 0, 1 and 2;
each R 1A , R 2A and R 3E is independently selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkylamino and C 2 -C 6 dialkylamino;
each R 1B is independently selected from the group consisting of H and C 1 -C 4 alkyl;
each R 1C is independently selected from the group consisting of hydroxy, halogen, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy and C 1 -C 6 haloalkoxy;
each R 1D is independently selected from the group consisting of cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy and C 2 -C 6 alkylcarbonyl;
each R 3A is independently selected from the group consisting of C 1 -C 4 alkyl and C 1 -C 4 haloalkyl;
each R 3B is independently selected from the group consisting of H, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl;
each R 3C is independently selected from the group consisting of H and C 1 -C 4 alkyl;
each R 3D is independently selected from the group consisting of H, amino, C 1 -C 4 alkyl and C 1 -C 4 alkylamino;
each R 3F is independently selected from the group consisting of hydroxy, halogen, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy and C 1 -C 6 haloalkoxy; and
each R 3G is independently selected from the group consisting of cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy and C 2 -C 6 alkylcarbonyl;
provided when i) Y 1 is N; Y 2 is CH; Y 3 is CBr; Y 4 is CH; and R 2 is Cl, then R 3 is other than 5-CF 3 , 5-CN or 5-NO 2 ; ii) Y 1 is N; Y 2 is CH; Y 3 is CBr; Y 4 is CH; and R 2 is Br, then R 3 is other than 5-CF 3 ; and iii) Y 1 is N; Y 2 is CCH 3 ; Y 3 is CCl; Y 4 is CCl; and R 2 is Cl, then m is other than 0.

2. A compound of claim 1 wherein
—Y 1 ═Y 2 —Y 3 ═Y 4 — including the nitrogen to which Y 1 and Y 4 are both attached is selected from the group consisting of

Z is O;
each R 1 is independently selected from the group consisting of hydrogen, halogen, cyano, SF 5 , CHO, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 1 -C 4 alkoxy, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, C 1 -C 4 haloalkoxy, C 3 -C 4 haloalkenyloxy, C 3 -C 4 haloalkynyloxy, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 2 -C 6 cyanoalkyl, C 2 -C 4 alkylthioalkyl, SO n R 1A , Si(CH 3 ) 3 and B(—OC(R 1B ) 2 C(R 1B ) 2 O—);
R 2 is selected from the group consisting of halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl;
each R 3 is independently selected from the group consisting of halogen, cyano, CHO, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 4 -C 8 alkylcycloalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 1 -C 4 alkoxy, C 3 -C 4 alkenyloxy, C 3 -C 4 alkynyloxy, C 1 -C 4 haloalkoxy, C 3 -C 4 haloalkenyloxy, C 3 -C 4 haloalkynyloxy, C 3 -C 6 cycloalkoxy, C 3 -C 6 halocycloalkoxy, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 2 -C 4 alkylcarbonyloxy, C 2 -C 6 cyanoalkyl, C(═O)N(R 3A )(R 3B ), C(═NOR 3C )H, SO n R 3E ; a phenyl ring optionally substituted with up to 5 substituents independently selected from R 3F ; and a 5- or 6-membered heteroaromatic ring containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 3 substituents independently selected from R 3F on carbon atom ring members and R 3G on nitrogen atom ring members; and
m is selected from the group consisting of 0, 1 and 2.

3. A compound of claim 2 wherein
—Y 1 ═Y 2 —Y 3 ═Y 4 — including the nitrogen to which Y 1 and Y 4 are both attached i

Assignees

• Du Pont
• Du Pont

Inventors

• Sharpe Paula Louise
• Stevenson Thomas Martin
• Deprez Nicholas Ryan
• Reddy Ravisekhara P
• Chittaboina Srinivas

Classifications

• A01N43/54

  1,3-Diazines; Hydrogenated 1,3-diazines · CPC title

• A01N43/56

  1,2-Diazoles; Hydrogenated 1,2-diazoles · CPC title

• A01N43/647

  Triazoles; Hydrogenated triazoles · CPC title

• C07D403/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D413/14

  containing three or more hetero rings · CPC title