Pyridazinone herbicides

Patent metadata

Field	Value
Publication number	US-10118917-B2
Application number	US-201515307831-A
Country	US
Kind code	B2
Filing date	Apr 27, 2015
Priority date	Apr 29, 2014
Publication date	Nov 6, 2018
Grant date	Nov 6, 2018

Abstract

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

wherein
X is O, S or NR 5 ; or X is —C(R 6 )═C(R 7 )—, wherein the carbon atom bonded to R 6 is also bonded to the carbon atom bonded to R 4 , and the carbon atom bonded to R 7 is also bonded to the phenyl ring moiety in Formula 1; and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , G and W 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 selected from Formula 1, N-oxides and salts thereof,

wherein
W is O or S;
R 1 is H, C 1 -C 7 alkyl, C 3 -C 8 alkylcarbonylalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 4 -C 7 alkylcycloalkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 3 -C 7 alkylthioalkyl, C 1 -C 7 alkoxy or benzyl; or a 5-, or 6-membered saturated or partially saturated heterocyclic ring containing ring members selected from carbon and up to 1 O and 1 S;
R 2 is H, halogen, —CN, —CHO, C 1 -C 7 alkyl, C 3 -C 8 alkylcarbonylalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 7 alkylcarbonyloxy, C 4 -C 7 alkylcycloalkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylamino, C 2 -C 8 dialkylamino, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy, C 1 -C 5 alkylthio, C 2 -C 3 alkoxycarbonyl; or phenyl optionally substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
X is O, S or NR 5 ; or
X is —C(R 6 )═C(R 7 )—, wherein the carbon atom bonded to R 6 is also bonded to the carbon atom bonded to R 4 , and the carbon atom bonded to R 7 is also bonded to the phenyl ring moiety in Formula 1;
each R 3 is independently halogen, —CN, nitro, C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, C 3 -C 5 cycloalkyl, C 4 -C 5 cycloalkylalkyl, C 1 -C 5 haloalkyl, C 3 -C 5 haloalkenyl, C 3 -C 5 haloalkynyl, C 2 -C 5 alkoxyalkyl, C 1 -C 5 alkoxy, C 1 -C 5 haloalkoxy, C 1 -C 5 alkylthio, C 1 -C 5 haloalkylthio or C 2 -C 5 alkoxycarbonyl;
R 4 , R 6 and R 7 are independently H, halogen, nitro, —CN, C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, C 3 -C 5 cycloalkyl, C 4 -C 5 cycloalkylalkyl, C 1 -C 5 haloalkyl, C 3 -C 5 haloalkenyl, C 3 -C 5 haloalkynyl, C 2 -C 5 alkoxyalkyl, C 1 -C 5 alkoxy, C 1 -C 5 haloalkoxy, C 1 -C 5 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 5 haloalkylthio or C 2 -C 5 alkoxycarbonyl;
R 5 is H, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
G is G 1 or W 1 G 1 ;
G 1 is H, —C(═O)R 8 , —C(═S)R 8 , —CO 2 R 9 , —C(═O)SR 9 , —S(O) 2 R 8 , —CONR 10 R 11 , —S(O) 2 NR 10 R 11 , or P(═O)(R 12 ) 2 ; or 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 4 alkoxyalkyl, C 3 -C 6 cycloalkyl or C 4 -C 7 cycloalkylalkyl; or a 5- or 6-membered heterocyclic ring;
W 1 is C 1 -C 4 alkanediyl or C 2 -C 4 alkenediyl;
R 8 and R 10 are independently C 1 -C 7 alkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 3 -C 7 cycloalkyl, C 1 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 4 -C 7 cycloalkylalkyl; or phenyl, benzyl or a 5- to 6-membered heterocyclic ring, each phenyl, benzyl or heterocyclic ring optionally substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
R 9 is C 1 -C 7 alkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 3 -C 7 cycloalkyl, C 2 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 4 -C 7 cycloalkylalkyl; or phenyl, benzyl, or 5- to 6-membered heterocyclic ring, each phenyl, benzyl or heterocyclic ring optionally substituted by halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
R 11 is H, C 1 -C 7 alkyl, C 2 -C 7 alkenyl, C 2 -C 7 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 1 -C 7 haloalkyl or C 2 -C 7 alkoxyalkyl;
R 12 is C 1 -C 7 alkyl or C 1 -C 7 alkoxy; and
n is 0, 1, 2, 3 or 4;
provided that when R 4 is H, then X is —C(R 6 )═C(R 7 )—.

2. A compound of claim 1 wherein
W is O;
X is O, S, —CH═CH—, —C(CH 3 )═CH—, —CH═CF—, —CH═CCl— or —CH═C(CH 3 )—;
R 1 is H, C 1 -C 7 alkyl, C 3 -C 8 alkylcarbonylalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 4 -C 7 alkylcycloalkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 3 -C 7 alkylthioalkyl, C 1 -C 7 alkoxy or benzyl;
R 2 is H, halogen, —CN, —CHO, C 1 -C 7 alkyl, C 3 -C 8 alkylcarbonylalkyl, C 3 -C 8 alkoxycarbonylalkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 7 alkylcarbonyloxy, C 4 -C 7 alkylcycloalkyl, C 3 -C 7 alkenyl, C 3 -C 7 alkynyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylamino, C 2 -C 8 dialkylamino, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 3 -C 7 haloalkenyl, C 2 -C 7 alkoxyalkyl, C 1 -C 7 alkoxy or C 1 -C 5 alkylthio;
each R 3 is independently halogen, —CN, C 1 -C 3 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio or C 1 -C 2 haloalkylthio;
R 4 is halogen, —CN, C 1 -C 3 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylthio or C 1 -C 2 haloalkylthio;
G is G 1 ;
G 1 is H, —C(═O)R 8 , —C(═S)R 8 , —CO 2 R 9 , —C(═O)SR 9 , —S(O) 2 R 8 , —CONR 10 R 11 , —S(O) 2 NR 10 R 11 or P(═O)(R 12 ) 2 ; or C 3 -C 6 cycloalkyl or C 4 -C 7 cycloalkylalkyl;
R 8 and R 10 are independently C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 3 haloalkyl or C 2 -C 7 alkoxyalkyl;
R 9 is C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl, C 2 -C 3 haloalkyl or C 2 -C 7 alkoxyalkyl;
R 11 is H, C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 3 haloalkyl or C 2 -C 7 alkoxyalkyl;
R 12 is C 1 -C 3 alkyl or C 1 -C 3 alkoxy; and
n is 0, 1, 2 or 3.

3. A compound of claim 2 wherein
X is —CH═CH—, —C(CH 3 )═CH—, —CH═CF—, —CH═CCl— or —CH═C(CH 3 )—;
R 1 is H, C 1 -C 7 alkyl, C 3 -C 8 alkoxycarbonylalkyl, C 4 -C 7 alkylcycloalkyl, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 alkoxyalkyl, C 3 -C 7 alkylthioalkyl, C 1 -C 7 alkoxy or benzyl;
R 2 is H, halogen, —CN, —CHO, C 1 -C 7 alkyl, C 2 -C 4 alkylcarbonyl, C 2 -C 7 alkylcarbonyloxy, C 4 -C 7 alkylcycloalkyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylamino, C 3 -C 7 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 2 -C 3 cyanoalkyl, C 1 -C 4 nitroalkyl, C 2 -C 7 haloalkoxyalkyl, C 1 -C 7 haloalkyl, C 2 -C 7 alkoxyalkyl or C 1 -C 7 alkoxy;
each R 3 is independently halogen, —CN, C 1 -C 2 alkyl, —CH═CH 2 , —C≡CH, cyclopropyl, C 1 -C 2 haloalkyl or C 1 -C 2 alkoxy;
R 4 is halogen, —CN, C 1 -C 2 alkyl, —CH═CH 2 , —C≡CH, cyclopropyl, C 1 -C 2 haloalkyl or C 1 -C 2 alkoxy;
G 1 is H, —C(═O)R 8 , —CO 2 R 9 , —S(O) 2 R 8 , —CONR 10 R 11 , —S(O) 2 NR 10 R 11 or P(═O)(R 12 ) 2 ;
R 8 , R 9 and R 10 are independently C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl or C 2 -C 7 alkoxyalkyl;
R 11 is H, C 1 -C 7 alkyl, C 3 -C 7 cycloalkyl or C 2 -C 7 alkoxyalkyl; and
R 12 is CH 3 or OCH 3 .

4. A compound of claim 3 wherein
X is —CH═CH—, —CH═CF—, —CH═CCl— or —CH═C(CH 3 )—;
R 1 is methyl, ethyl, n-propyl or 2-methoxyethyl;
R 2 is H, methyl, ethyl, n-propyl, CF 3 or methoxy;
each R 3 is independently halogen, —CN, methyl, ethyl, —CH═CH 2 , —C≡CH, cyclopropyl, CF 3 , methoxy or ethoxy;
R 4 is halogen, —CN, methyl, ethyl, —CH═CH 2 , —C≡CH, cyclopropyl, CF 3 , methoxy or ethoxy;
G 1 is H, —C(═O)R 8 , —CO 2 R 9 , —S(O) 2 R 8 or P(═O)(R 12 ) 2 ;
R 8 and R 9

Assignees

• Du Pont

Inventors

• Selby Thomas Paul
• Deprez Nicholas Ryan
• Stevenson Thomas Martin
• Taggi Andrew Edmund
• Debergh John Robbins

Classifications

• C07D333/60

  Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• C07D307/81

  Radicals substituted by nitrogen atoms not forming part of a nitro radical · CPC title

• C07D237/18

  Sulfur atoms · CPC title

• A01N25/32

  Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions · CPC title

• C07D237/16

  Two oxygen atoms · CPC title