Herbicidal pyridazinone derivatives

Patent metadata

Field	Value
Publication number	US-9693556-B2
Application number	US-201214349972-A
Country	US
Kind code	B2
Filing date	Oct 3, 2012
Priority date	Oct 4, 2011
Publication date	Jul 4, 2017
Grant date	Jul 4, 2017

Abstract

The present invention provides a compound of Formula (I) or an agronomically acceptable salt thereof, wherein: R 2 is selected from the group consisting of (A1), (A2) and (A3) wherein X 1 is N or CR 7 X 2 is N or CR 8 X 3 is N or CR 9 X 4 is N or CR 6 R 1 , R 3 , R 4 , R 5 R 6 , R 7 , R 8 and R 9 are as defined herein. The invention further relates to herbicidal compositions which comprise a compound of Formula (I), and to their use for controlling weeds, in particular in crops of useful plants.

First claim

The invention claimed is:

1. A compound Formula (I):

or an agronomically acceptable salt thereof,
wherein:—
R 1 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy-C 1 -C 3 -alkyl, C 3 -C 6 cycloalkylC 1 -C 3 -alkyl-, and tetrahydropyranyl-;
R 2 is selected from the group consisting of A1, A2 and A3

wherein
X 1 is N or CR 7 ;
X 2 is N or CR 8 ;
X 3 is N or CR 9 ;
X 4 is N or CR 6 ;
R 3 is selected from the group consisting of hydrogen, halo, nitro, amino, cyano, C 1 -C 6 alkyl, C 1 -C 3 alkoxy-, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy-C 1 -C 3 -alkyl, C 3 -C 6 cycloalkyl-C 1 -C 3 -alkyl, C 1 -C 6 alkyl-S(O) p -, C 1 -C 6 alkyl-S(O) p -C 1 -C 3 -alkyl, C 1 -C 6 haloalkyl-S(O) p -, C 1 -C 3 alkylamino, C 1 -C 3 dialkylamino and C 1 -C 6 haloalkyl-S(O) p -C 1 -C 3 -alkyl;
R 4 is selected from the group consisting of hydrogen, C 1 -C 6 alkylcarbonyl-, arylcarbonyl-, C 1 -C 6 alkoxycarbonyl-, C 1 -C 6 alkyl-S(O) p -, C 1 -C 6 alkyl-S(O) p carbonyl- and aryl-S(O) p -, wherein said aryl groups may be optionally substituted by one or more R 11 ;
R 5 is selected from the group consisting of hydroxyl, halogen, C 1 -C 6 alkyl, C 1 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy-, C 2 -C 6 alkenyloxy-, C 3 -C 6 cycloalkylC 1 -C 3 -alkyl-, C 1 -C 6 alkoxyC 1 -C 3 alkyl-, C 1 -C 6 alkoxy-C 2 -C 6 alkoxy-, C 1 -C 6 alkoxy-C 2 -C 6 alkoxy-C 1 -C 3 alkyl-,C 1 -C 6 haloalkoxy-, C 1 -C 6 haloalkoxy-C 1 -C 3 alkyl-, C 1 -C 6 alkyl-S(O) p -, C 1 -C 6 haloalkyl-S(O) p -, aryl, aryl-S(O) p -, heterocyclyl, heterocyclyl-S(O) p -, aryloxy-, aryl-C 2 -C 6 alkyl-, aryl-C 1 -C 6 alkoxy-, heterocyclyloxy-, heterocyclyl-C 1 -C 3 alkoxy-C 1 -C 3 alkyl-, hydroxycarbonyl, hydroxycarbonyl-C 1 -C 3 alkoxy-, C 1 -C 3 alkoxycarbonyl-, C 1 -C 3 alkoxycarbonyl-C 1 -C 3 alkoxy-, C 1 -C 3 alkylamino-, C 1 -C 3 dialkylamino-, C 1 -C 3 alkylamino-S(O) p -, C 1 -C 3 alkylamino-S(O) p -C 1 -C 3 alkyl-, C 1 -C 3 dialkylamino-S(O) p -, C 1 -C 3 dialkylamino-S(O) p - C 1 -C 3 alkyl-, C 1 -C 3 alkylaminocarbonyl-, C 1 -C 3 alkylaminocarbonyl-C 1 -C 3 alkyl-, C 1 -C 3 dialkylaminocarbonyl-, C 1 -C 3 dialkylaminocarbonyl-C 1 -C 3 alkyl-, C 1 -C 3 alkylcarbonylamino-, C 1 -C 3 alkyl-S(O) p -amino-, C 1 -C 3 alkyl-S(O) p -C 1 -C 3 alkylamino-, C 1 -C 3 alkyl-S(O) p - aminoC 1 -C 3 alkyl-, cyano and nitro, wherein said heterocyclyls are five or six membered heterocyclyls containing from one to three heteroatoms each independently selected from the group consisting of oxygen, nitrogen and sulphur, and wherein the aryl or heterocyclyl components may be optionally substituted by one or more substituents selected from the group consisting of halo, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 6 alkyl-S(O) p -, phenyl, cyano and nitro;
R 6 and R 9 are independently selected from the group consisting of hydrogen, hydroxyl, halogen, C 1 -C 6 alkyl, C 1 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy-, C 2 -C 6 alkenyloxy-, C 3 -C 6 cycloalkylC 1 -C 3 -alkyl-, C 1 -C 6 alkoxyC 1 -C 3 alkyl-, C 1 -C 6 alkoxy-C 2 -C 6 alkoxy-, C 1 -C 6 alkoxy-C 2 -C 6 alkoxy-C 1 -C 3 alkyl-, C 1 -C 6 haloalkoxy-, C 1 -C 6 haloalkoxy-C 1 -C 3 alkyl-, C 1 -C 6 alkyl-S(O) p -, C 1 -C 6 haloalkyl-S(O) p -, aryl, aryl-S(O) p -, heterocyclyl, heterocyclyl-S(O) p -, aryloxy-, aryl-C 2 -C 6 alkyl-, aryl-C 1 -C 6 alkoxy-, heterocyclyloxy-, heterocyclyl-C 1 -C 3 alkoxy-C 1 -C 3 alkyl-, hydroxycarbonyl, hydroxycarbonyl-C 1 -C 3 alkoxy-, C 1 -C 3 alkoxycarbonyl-, C 1 -C 3 alkoxycarbonyl-C 1 -C 3 alkoxy-, C 1 -C 3 alkylamino-, C 1 -C 3 dialkylamino-, C 1 -C 3 alkylamino-S(O) p -, C 1 -C 3 alkylamino-S(O) p -C 1 -C 3 alkyl-, C 1 -C 3 dialkylamino-S(O) p -, C 1 -C 3 dialkylamino-S(O) p -C 1 -C 3 alkyl-, C 1 -C 3 alkylaminocarbonyl-, C 1 -C 3 alkylaminocarbonyl-C 1 -C 3 alkyl-, C 1 -C 3 dialkylaminocarbonyl-, C 1 -C 3 dialkylaminocarbonyl-C 1 -C 3 alkyl-, C 1 -C 3 alkylcarbonylamino-, C 1 -C 3 alkyl-S(O) p -amino-, C 1 -C 3 alkyl-S(O) p -C 1 -C 3 alkylamino-, C 1 -C 3 alkyl-S(O)p- aminoC 1 -C 3 alkyl-, cyano and nitro, wherein said heterocyclyls are five or six membered heterocyclyls containing from one to three heteroatoms each independently selected from the group consisting of oxygen, nitrogen and sulphur, and wherein the aryl or heterocyclyl components may be optionally substituted by one or more substituents selected from the group consisting of halo, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 6 alkyl-S(O) p -, phenyl, cyano and nitro;
R 7 and R 8 are independently selected from the group consisting of hydrogen, halogen, C 1 -C 3 alkyl-, C 1 -C 3 alkoxy-, C 2 -C 3 alkenyl-, C 2 -C 3 alkynyl-, C 1 -C 3 haloalkyl- and C 1 -C 3 haloalkoxy-;
and wherein R 5 and R 9 can together form a saturated or unsaturated 5- or 6-membered carbocyclic or heterocyclic ring, said heterocyclic ring comprising one or more nitrogen and/or oxygen heteroatoms, the 5- or 6-membered ring being optionally substituted by one or more R 12 ; or
R 6 and R 9 can together form a saturated or unsaturated 5- or 6-membered carbocyclic or heterocyclic ring, said heterocyclic ring comprising one or more hetereoatoms selected from the group consisting of nitrogen, oxygen and S(O) 2, the 5- or 6-membered ring being optionally substituted by one or more R 12 ; or
R 6 and R 8 can together form a saturated or unsaturated 5- or 6-membered carbocyclic or heterocyclic ring, said heterocyclic ring comprising one or more nitrogen heteroatoms, the 5- or 6-membered ring being optionally substituted by one or more R 13 ; and
R 11 is selected from the group consisting of halo-, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl and C 1 -C 6 alkoxy;
R 12 is selected from the group of hydrogen, cyano, halo-, oxy-, C 1 -C 3 alkylS(O)p-, C 1 -C 3 alkyl, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, C 1 -C 3 alkoxy and C 1 -C 3 haloalkyl;
R 13 is selected from the group of hydrogen, cyano, halo-, C 1 -C 3 alkylS(O)p-, C 1 -C 3 alkyl, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, morpholinyl- and C 1 -C 3 haloalkyl; and
=0, 1 or 2.

2. A compound according to claim 1 , wherein R 3 and/or R 4 is hydrogen.

3. A compound according to claim 1 , wherein R 2 is selected from the group consisting of A1a, A1b, A1c, A1d, A1e, A1f, A1g, A1h, A2a, A2b, A3a A3b and A3 c:

wherein R 5 , R 6 , R 7 , R 8 , R 9 and R 13 are as defined previously and n is 0, 1, 2 or 3.

4. A compound according to claim 3 , wherein R 2 is A1a.

5. A compound according to claim 1 , wherein R 5 is selected from the group consisting of hydroxyl, halo, C 1 -C 6 alkyl, C 1 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkoxyC 1 -C 3 alkyl, C 1 -C 6 alkoxy-C 2 -C 6 alkoxy-C 1 -C 3 alkyl, C 1 -C 6 haloalkoxyC 1 -C 3 alkyl, C 1 -C 6 alkyl-S(O) p -, aryl, aryloxy, heterocyclyl-C 1 -C 3 alkoxy-C 1 -C 3 alkyl, C 1 -C 3 dialkylamino-, C 1 -C 3 alkyl-S(O) p -amino-C 1 -C 3 dialkyl, cyano and nitro.

6. A compound according to claim 5 , wherein R 5 is selected from the group consisting of chloro, fluoro, methyl, trifluoromethyl, 2-fluoroethyl-, methoxyethoxymethyl-,

Assignees

• Syngenta Ltd

Inventors

• Bhonoah Yunas
• Elliott Alison Clare
• Gaulier Steven
• Ling Kenneth
• Mitchell Glynn
• Morris James Alan
• Rzepa Paula Rocha
• Viner Russell Colin

Classifications

• C07D495/10

  Spiro-condensed systems · CPC title

• C07D405/12

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

• C07D405/04

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

• A01N43/58 Primary

  1,2-Diazines; Hydrogenated 1,2-diazines · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title