Herbicidal substituted pyrimidinyloxy benzene compounds

Patent metadata

Field	Value
Publication number	US-2016340340-A1
Application number	US-201415101095-A
Country	US
Kind code	A1
Filing date	Dec 9, 2014
Priority date	Dec 10, 2013
Publication date	Nov 24, 2016
Grant date	—

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 N or CR 1 , provided no more than 3 of Y 1 , Y 2 , Y 3 and Y 4 are N;
Z is O or S;
each R 1 is independently 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 or B(—OC(R 1B ) 2 C(R 1B ) 2 O—); or a phenyl ring optionally substituted with up to 5 substituents independently selected from R 1C ; or 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 1C on carbon atom ring members and R 1D on nitrogen atom ring members;
R 2 is 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 or C 3 -C 6 cycloalkyl;
m is 0, 1, 2 or 3;
each R 3 is independently 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 ; or a phenyl ring optionally substituted with up to 5 substituents independently selected from R 3F ; or 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; or pyrimidinyloxy;
each n is independently 0, 1 or 2;
each R 1A , R 2A and R 3E is independently C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkylamino or C 2 -C 6 dialkylamino;
each R 1B is independently H or C 1 -C 4 alkyl;
each R 1C is independently hydroxy, halogen, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy;
each R 1D is independently cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 2 -C 6 alkylcarbonyl;
each R 3A is independently C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
each R 3B is independently H, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
each R 3C is independently H or C 1 -C 4 alkyl;
each R 3D is independently H, amino, C 1 -C 4 alkyl or C 1 -C 4 alkylamino;
each R 3F is independently hydroxy, halogen, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy; and
each R 3G is independently cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or 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

Z is O;
each R 1 is independently 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 or B(—OC(R 1B ) 2 C(R 1B ) 2 O—);
R 2 is halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
each R 3 is independently 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 ; or a phenyl ring optionally substituted with up to 5 substituents independently selected from R 3F ; or 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 0, 1 or 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 is selected from Q-2 and Q-5;
each R 1 is independently hydrogen, 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 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 4 alkylthioalkyl or SO n R 1A ;
R 2 is halogen or C 1 -C 4 alkyl;
each R 3 is independently 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 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 6 alkoxyalkyl, C 2 -C 6 haloalkoxyalkyl, C 2

Assignees

• Du Pont

Inventors

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

Classifications

• 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

• A01N43/54

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

• C07D413/14

  containing three or more hetero rings · CPC title