JP-2026514482-A - herbicidal derivatives

Abstract

A compound of formula (I) (wherein the formula, the substituents are as defined in claim 1). The present invention further relates to herbicidal compositions comprising a compound of formula (I), and to the use of a compound of formula (I) for controlling weeds, particularly in crops of useful plants. [Chemical formula 1]

Inventors

• モリス ジェイムズ アラン
• ウォーリー ルイーザ
• クリストファーセン アビー ルイス
• ゴム アンドリュー
• マスタンドレア マルコ ミケーレ

Assignees

• シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト

Dates

Publication Date

20260511

Application Date

20240423

Priority Date

20230427

Claims (15)

1. Compound of formula (I): ( R1 is a C1 - C6 alkyl, C1 - C6 alkoxy, C2 - C6 alkenyl, C2 - C6 alkynyl, C1 - C6 alkoxyC1- C6 alkyl, or C3 -C6 cycloalkyl ; R2 is phenyl or heteroaryl, where the heteroaryl portion is a five- or six-membered aromatic ring containing one, two, three, or four heteroatoms individually selected from N, O, and S, and each phenyl and heteroaryl portion may be optionally substituted with one, two, three, or four groups, which may be the same or different, represented by R5 ; R3 is hydrogen or a C1 - C6 alkyl group; R4 is hydrogen or halogen; R5 is cyano, nitro, halogen, C1 - C6 alkyl, C1-C6 alkoxy, C1 - C6 haloalkyl, C1 - C6 haloalkoxy, C1 - C6 alkoxyC1-C6 alkyl, C1 - C6 alkyl sulfanyl, C1 - C6 alkyl sulfinyl, C1 - C6 alkyl sulfonyl, C1 - C6 alkyl sulfonyl, C1 - C6 alkyl sulfonamide, C1 - C6 alkyl carbonyl, C1 - C6 alkoxycarbonyl, C1 - C6 alkylaminocarbonyl, C3 - C6 cycloalkyl, C3 - C6 cycloalkylaminocarbonyl, or N,N-di( C1 - C4 alkyl)aminocarbonyl; and X is a halogen; or its salt or N-oxide.
2. The compound according to claim 1, wherein R1 is a C1 - C3 alkyl group.
3. The compound according to claim 1 or claim 2, wherein R2 is phenyl or pyridyl, and each phenyl and pyridyl moiety may be optionally substituted with one or two groups, which may be the same or different, represented by R5 .
4. The compound according to any one of claims 1 to 3, wherein R2 is a phenyl which may be optionally substituted with one or two groups which may be the same as or different from R5 .
5. The compound according to any one of claims 1 to 4, wherein R3 is hydrogen or a C1 - C3 alkyl group.
6. The compound according to any one of claims 1 to 5, wherein R4 is hydrogen or bromo.
7. The compound according to any one of claims 1 to 6, wherein X is chloro, fluoro, or iodine.
8. The compound according to any one of claims 1 to 7, wherein R5 is cyano or halogen.
9. The compound according to any one of claims 1 to 8, wherein R1 is ethyl.
10. The compound according to any one of claims 1 to 9, wherein R2 is 3,4-dichlorophenyl or 3-chloro-4-cyanophenyl.
11. A herbicide composition comprising a compound according to any one of claims 1 to 10 and an agriculturally acceptable compounding agent.
12. The herbicide composition according to claim 11, further comprising at least one additional biological agent.
13. The herbicide composition according to claim 12, wherein the additional pesticide is a herbicide or a herbicide phytotoxicity reducer.
14. A method for controlling weeds in a habitat, comprising applying a weed control amount of the composition described in any one of claims 11 to 13 to the said habitat of the weeds.
15. Use of the compound of formula (I) according to any one of claims 1 to 10 as a herbicide.

Description

This invention relates to herbicidal pyridone derivatives having herbicidal activity, for example, as active ingredients. The invention also relates to pesticide compositions comprising at least one pyridone derivative, processes for preparing these compounds, and the use of pyridone derivatives or compositions for controlling weeds in agriculture or horticulture, particularly in crops of useful plants. European Patent No. 0239391, European Patent No. 0127313, European Patent No. 0040082, British Patent No. 2182931, British Patent No. 2328614, International Publication No. 2022117445, International Publication No. 2022117446, and International Publication No. 2023/110664 describe pyridone derivatives as herbicides. When a substituent is indicated as "optionally substituted," this means that it may have one or more identical or different substituents, for example, one, two, or three R6 substituents. For example, C1 - C6 alkyl groups substituted with one, two, or three halogens may include, but are not limited to, -CH2Cl , -HCl2 , -CCl3 , -CH2F , -CHF2, -CF3 , -CH2CF3 , or -CF2CH3 groups. Another example of C1 - C6 alkoxy groups substituted with one, two, or three halogens may include, but are not limited to, CH2ClO- , CHCl2O- , CCl3O- , CH2FO- , CHF2O- , CF3O- , CF3CH2O- , or CH3CF2O- groups. As used herein, the term "cyano" refers to a -CN group. As used herein, the term "halogen" refers to fluorine (fluoro), chlorine (chloro), bromine (bromo), or iodine (iod). As used herein, the term "nitro" means a -NO2 group. As used herein, the term "acetyl" means the -C(O) CH3 group. As used herein, =O refers to an oxo group, such as that found in a carbonyl (-C(=O)-) group. As used herein, the term " C1 - C6 alkyl" refers to a linear or branched hydrocarbon chain radical consisting only of carbon and hydrogen atoms, containing no unsaturation, and having 1 to 6 carbon atoms, with the remainder of the molecule bonded by single bonds. " C1 -C4 alkyl" and " C1 - C3 alkyl" should be interpreted accordingly as appropriate. Examples of C1 - C6 alkyls include, but are not limited to, methyl, ethyl, n-propyl, and their isomers, such as isopropyl. The " C1 - C6 alkylene" group refers to the corresponding definition of C1- C6 alkyl, except that such a group is bonded to the remainder of the molecule by two single bonds. The term " C1 - C2 alkylene" should be interpreted accordingly as appropriate. Examples of C1 - C6 alkylenes include, but are not limited to, -CH2- , -CH2CH2- , and -( CH2 ) 3- . As used herein, the term " C1 - C6 haloalkyl" refers to a C1- C6 alkyl radical, as generally defined above, that is substituted by one or more of the same or different halogen atoms. The terms " C1 - C4 haloalkyl" and " C1 - C3 haloalkyl" should be interpreted accordingly as appropriate. Examples of C1 - C6 haloalkyls include, but are not limited to, trifluoromethyl. As used herein, the term " C1 - C6 alkoxy" refers to a radical of the formula -OR a (wherein Ra is a C1 - C6 alkyl radical as generally defined above). The terms " C1 - C4 alkoxy" and " C1 - C3 alkoxy" should be interpreted accordingly as appropriate. Examples of C1 - C6 alkoxy include, but are not limited to, methoxy, ethoxy, 1-methylethoxy (isopropoxy), and propoxy. As used herein, the term " C1 - C6 haloalkoxy" refers to a C1- C6 alkoxy, as generally defined above, that is substituted with one or more of the same or different halogen atoms. The terms " C1 - C4 haloalkoxy" and " C1 - C3 haloalkoxy" should be interpreted accordingly as appropriate. Examples of C1 - C6 haloalkoxy include, but are not limited to, trifluoromethoxy. As used herein, the term " C2 - C6 alkenyl" refers to a linear or branched hydrocarbon chain radical consisting only of carbon and hydrogen atoms, containing at least one double bond which may be in either an (E) or (Z) stereoconfiguration, and having 2 to 6 carbon atoms, with the remainder of the molecule bonded by single bonds. The term " C2 - C3 alkenyl" should be interpreted accordingly as appropriate. Examples of C2 - C6 alkenyls include, but are not limited to, ethenyl (vinyl), propa-1-enyl, propa-2-enyl (allyl), and buta-1-enyl. As used herein, the term " C2 - C6 alkynyl" refers to a linear or branched hydrocarbon chain group consisting only of carbon and hydrogen atoms, containing at least one triple bond, and having 2 to 6 carbon atoms, bonded to the remainder of the molecule by single bonds. The term " C2 - C3 alkynyl" should be interpreted accordingly as appropriate. Examples of C2 - C6 alkynyls include, but are not limited to, ethynyl, propan-1-inyl, and buta-1-inyl. As used herein, the term “ C2 - C6 alkenyloxy” refers to a C2 - C6 alkenyl radical, as generally defined above, that is bonded to the rest of the molecule via an oxygen atom. As used herein, the term " C2 - C6 alkynyloxy" refers to a C2 - C6 alkynyl radical, as generally defined above, that is bonded to the rest of the molecule via an oxygen atom. As used herein, the term