Herbicidal Inducer

Abstract

Compounds of formula (I), in which the substituents are as defined in claim 1. The present invention further relates to herbicidal compositions comprising compounds of formula (I) and to the use of compounds of formula (I) for controlling weeds, especially in crops of useful plants. TIFF2023551933000175.tif51161

Description

[Technical Field]

[0001] The present invention relates, for example, to herbicidal pyridone derivatives as active ingredients having herbicidal activity. The present 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 in the control of weeds in agriculture or horticulture, particularly in crops of useful plants. [Background technology]

[0002] European Patent No. 0239391, European Patent No. 0127313, European Patent No. 0040082, and British Patent No. 2182931 describe pyridone derivatives as herbicides. [Overview of the project] [Means for solving the problem]

[0003] According to the present invention, a compound of formula (I): [ka] (In the formula, X is O, NR 6 or S; R 1 It is a C1-C6 alkyl group; R 2 is phenyl or heteroaryl, and the heteroaryl moiety is a 5-membered or 6-membered aromatic ring containing 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, and each phenyl and heteroaryl moiety is R 7 It may be arbitrarily substituted with one, two, three, or four bases, which may be identical or different, represented by; R 3is hydrogen, C1-C6 alkyl, N,N-di(C1-C3 alkyl)amino, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, phenyl or phenyl C1-C3 alkyl, and the phenyl moiety is optionally substituted with the same or different 1, 2, 3 or 4 groups represented by R 8 and may be optionally substituted with the same or different 1, 2, 3 or 4 groups represented by R R 4 is C3-C6 cycloalkenyl, phenyl, phenyl C1-C2 alkyl, phenyl C1-C2 alkenyl, heterocyclyl (where the heterocyclyl moiety is a 4-, 5- or 6-membered non-aromatic monocyclic ring containing 1, 2 or 3 heteroatoms individually selected from N, O and S), or heteroaryl (where the heteroaryl moiety is a 5- or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms individually selected from N, O and S), and where the phenyl, heterocyclyl and heteroaryl moieties are each optionally substituted with the same or different 1, 2, 3 or 4 groups represented by R 9 and may be optionally substituted with the same or different 1, 2, 3 or 4 groups represented by R; or R 4 is a 6- to 10-membered ring system optionally containing 1, 2 or 3 heteroatoms individually selected from N, O and S, the ring system is optionally substituted with 1 or 2 groups represented by R 12 and the ring system is optionally attached to the remainder of the molecule via a C1-C2 alkylene linker; R 5 is halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy or C1-C4 alkoxy C1-C4 alkyl; R 6 is hydrogen, C1-C3 alkyl or C1-C6 alkoxy; R 7The compounds are cyano, nitro, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 alkoxyC1-C6 alkyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonamide, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl, N,N-di(C1-C4 alkyl)aminocarbonyl, or phenyl, and each phenyl portion is R 10 It may be arbitrarily substituted with one, two, or three bases, which may be identical or different, represented by; R 8 These are halogens, cyanos, C1-C3 alkyls, or C1-C3 alkoxys; R 9 These include cyano, nitro, halogen, oxo, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1- C6 alkylsulfonamide, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkoxy, N,N-di(C1-C4 alkyl)aminosulfonyl, C3-C6 cycloalkylaminocarbonyl, N,N-di(C1-C4 alkyl)aminocarbonyl, phenoxy or benzyloxy, where each cycloalkyl or phenyl portion is R 12 It may be arbitrarily substituted with one or two bases, which may be identical or different, represented by; or Any two adjacent R 9The groups, together with the carbon atoms to which they are bonded, can form a five-membered or six-membered heterocyclyl ring containing one or two heteroatoms selected from O and N, and the heterocyclyl ring is R 11 It may be arbitrarily substituted with one, two, three, or four bases, which may be identical or different, represented by; R 10 These are halogens, C1-C3 alkyls, or C1-C3 alkoxys; R 11 These are halogens, C1-C3 alkyls, or C1-C3 alkoxys; R 12 (These are cyano, halogen, C1-C3 alkyl, or C1-C3 alkoxy compounds.) Alternatively, a salt or N-oxide thereof is provided.

[0004] Surprisingly, the novel compound of formula (I) was found to possess a highly advantageous level of herbicidal activity for practical purposes.

[0005] According to a second aspect of the present invention, an agricultural composition is provided comprising a herbicidally effective amount of the compound of formula (I) according to the present invention. Such an agricultural composition may further comprise at least one additional active ingredient and / or an agriculturally acceptable diluent or carrier.

[0006] A third aspect of the present invention provides a method for controlling weeds in a habitat, comprising the step of applying a composition containing a compound of formula (I) in a weed control amount to the habitat.

[0007] According to a fourth aspect of the present invention, the use of a compound of formula (I) as a herbicide is provided. [Modes for carrying out the invention]

[0008] When it is stated that a substituent "may be optionally substituted", this means one or more equivalent or different substituents, for example, one, two or three R 7This means that the substituent may or may not be present. For example, C1-C6 alkyl groups substituted with one, two, or three halogens are not particularly limited, but may include -CH2Cl, -CHCl2, -CCl3, -CH2F, -CHF2, -CF3, -CH2CF3, or -CF2CH3 groups. Other examples of C1-C6 alkoxy groups substituted with one, two, or three halogens are not particularly limited, but may include CH2ClO-, CHCl2O-, CCl3O-, CH2FO-, CHF2O-, CF3O-, CF3CH2O-, or CH3CF2O- groups.

[0009] As used herein, the term "cyano" means the -CN group.

[0010] As used herein, the term "halogen" refers to fluorine (fluoro), chlorine (chloro), bromine (bromo), or iodine (iod).

[0011] As used herein, the term "nitro" means the -NO2 group.

[0012] As used herein, the term "acetyl" means the -C(O)CH3 group.

[0013] In this specification, =O refers to an oxo group found, for example, in a carbonyl (-C(=O)-) group.

[0014] As used herein, the term "C1-C6 alkyl" refers to a linear or branched hydrocarbon group composed solely of carbon and hydrogen atoms, unsaturated, having 1 to 6 carbon atoms, and bonded to the remainder of the molecule by single bonds. "C1-C4 alkyl" and "C1-C3 alkyl" should be interpreted similarly. Examples of C1-C6 alkyls, but not limited to these, include 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 similarly. Examples of C1-C6 alkylenes, but not limited to these, include -CH2-, -CH2CH2-, and -(CH2)3-.

[0015] As used herein, the term "C1-C6 haloalkyl" refers to a C1-C6 alkyl group, as generally defined above, that is substituted with one or more identical or different halogen atoms. The terms "C1-C4 haloalkyl" and "C1-C3 haloalkyl" should be interpreted similarly. Examples of C1-C6 haloalkyls, but not limited to these, include trifluoromethyl.

[0016] As used herein, the term "C1-C6 alkoxy" means R a The formula -OR is generally defined as a C1-C6 alkyl group as described above. a This refers to the group of C1-C4 alkoxy. The terms "C1-C4 alkoxy" and "C1-C3 alkoxy" should be interpreted similarly. Examples of C1-C6 alkoxy, but not limited to these, include methoxy, ethoxy, 1-methylethoxy (isopropoxy), and propoxy.

[0017] As used herein, the term "C1-C6 haloalkoxy" refers to a C1-C6 alkoxy group, as generally defined above, that is substituted with one or more identical or different halogen atoms. The terms "C1-C4 haloalkoxy" and "C1-C3 haloalkoxy" should be interpreted similarly. Examples of C1-C6 haloalkoxys include, but are not limited to, trifluoromethoxy.

[0018] As used herein, the term "C2-C6 alkenyl" refers to a linear or branched hydrocarbon chain group having 2 to 6 carbon atoms, composed only of carbon and hydrogen atoms, containing at least one double bond capable of an (E)- or (Z)- configuration, and the remainder of the molecule bonded by single bonds. The term "C2-C3 alkenyl" should be interpreted similarly. Examples of C2-C6 alkenyls, but not limited to these, include ethenyl (vinyl), prop-1-enyl, prop-2-enyl (allyl), and buta-1-enyl.

[0019] As used herein, the term "C2-C6 alkynyl" refers to a linear or branched hydrocarbon chain group composed solely of carbon and hydrogen atoms, containing at least one triple bond, having 2 to 6 carbon atoms, and bonded to the remainder of the molecule by single bonds. The term "C2-C3 alkynyl" should be interpreted similarly. Examples of C2-C6 alkynyls, but not limited to these, include ethynyl, prop-1-inyl, and buta-1-inyl.

[0020] As used herein, the term "C1-C6 alkoxy C1-C6 alkyl" means R b These are generally C1-C6 alkyl groups as defined above, and R a Formula R is generally defined as a C1-C6 alkylene group as described above. b Ure a It refers to the group with the hyphen. The term "C1-C4 alkoxy C1-C4 alkyl" should be interpreted similarly.

[0021] As used herein, the term "C1-C6 alkoxy C1-C6 alkoxy" means R a and R b However, each is independently of the C1-C6 alkyl group of formula R as generally defined above. b Ure a This refers to the O- group. The terms "C1-C4 alkoxy" and "C1-C3 alkoxy" should be interpreted similarly.

[0022] As used herein, the term "C3-C6 cycloalkyl" refers to a monocyclic saturated ring system containing 3 to 6 carbon atoms. The terms "C3-C5 cycloalkyl" and "C3-C4 cycloalkyl" should be interpreted similarly. Examples of C3-C6 cycloalkyls, but not limited to these, include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0023] As used herein, the term "C3-C6 cycloalkenyl" refers to a monocyclic unsaturated ring system containing at least one double bond and 3 to 6 carbon atoms. The terms "C3-C5 cycloalkenyl" and "C3-C4 cycloalkenyl" should be interpreted similarly. Examples of C3-C6 cycloalkenyls, but not limited to these, include cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl.

[0024] As used herein, the term "C3-C6 cycloalkyl C1-C6 alkyl" refers to a C3-C6 cycloalkyl ring bonded to the remainder of the molecule by the C1-C6 alkylene linker as defined above. Examples of C3-C6 cycloalkyl C1-C6 alkyls, but not limited to these, include cyclopropylmethyl.

[0025] As used herein, the term "C3-C6 cycloalkylaminocarbonyl" refers to a C3-C6 cycloalkyl ring bonded to the remainder of the molecule via an -NHC(O)-linker. Examples of C3-C6 cycloalkylaminocarbonyls, but not limited to these, include cyclopropylcarbamoyl (i.e., cyclopropylaminocarbonyl).

[0026] As used herein, the term "benzyloxy" refers to the benzyl ring bonded to the remainder of the molecule via an oxygen atom.

[0027] As used herein, the term "phenyl C1-C3 alkyl" refers to a phenyl ring bonded to the remainder of the molecule via the C1-C3 alkylene linker defined above. The term "phenyl C1-C2 alkyl" should be interpreted similarly.

[0028] As used herein, the term "phenyl C1-C3 alkenyl" refers to a phenyl ring bonded to the remainder of the molecule via the C1-C3 alkenyl moiety defined above. The term "phenyl C1-C2 alkenyl" should be interpreted similarly.

[0029] As used herein, the term "heterocyclyl" refers to a stable four-membered, five-membered, or six-membered non-aromatic monocyclic ring containing one, two, or three heteroatoms, where the heteroatoms are individually selected from nitrogen, oxygen, and sulfur. The heterocyclyl group may be bonded to the remainder of the molecule via carbon atoms or heteroatoms. Examples of heterocyclyls, but not limited to, include azilidinyl, azetidinyl, oxetanyl, thietanyl, tetrahydrofuryl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, piperidinyl, piperazinyl, morpholinyl, dioxolanyl, dithiolanyl, and thiazolidinyl.

[0030] As used herein, the term "heteroaryl" refers to a five-membered or six-membered aromatic monocyclic ring group containing one, two, three, or four heteroatoms individually selected from nitrogen, oxygen, and sulfur. Examples of heteroaryls, but not limited to, include furanyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridadinyl, pyrimidyl, or pyridyl.

[0031] As used herein, the term "C1-C6 alkylcarbonyl" means R a The formula -C(O)R is generally defined as a C1-C6 alkyl group as described above. a This refers to the group. Examples of C1-C6 alkylcarbonyl groups include, but are not limited to, acetyl.

[0032] As used herein, the term "C1-C6 alkoxycarbonyl" means R a The formula -C(O)OR is generally defined as a C1-C6 alkyl group as described above. a It refers to the base of.

[0033] As used herein, the term "C1-C6 alkylaminocarbonyl" means R a The formula -C(O)NHR is generally defined as a C1-C6 alkyl group as described above. a This refers to the group. Examples of C1-C6 alkylaminocarbonyl groups include, but are not limited to, ethylcarbamoyl (i.e., ethylaminocarbonyl).

[0034] As used herein, the term "N,N-di(C1~C4 alkyl)aminocarbonyl" means R a and R b Each of these is a C1-C4 alkyl group as generally defined above, with the formula -C(O)N(R a )(R bThis refers to the group of ). The term "N,N-di(C1~C3 alkyl)aminocarbonyl" should be interpreted similarly. Examples of N,N-di(C1~C4 alkyl)aminocarbonyl include, but are not limited to, dimethylcarbamoyl (i.e., N,N-di(methyl)aminocarbonyl).

[0035] As used herein, the term "N,N-di(C1~C4 alkyl)aminosulfonyl" means R a and R b Each of these is a C1-C4 alkyl group as generally defined above, with the formula -S(O)2N(R a )(R b This refers to the group of ). The term "N,N-di(C1~C3 alkyl)aminosulfonyl" should be interpreted similarly. Examples of N,N-di(C1~C4 alkyl)aminosulfonyl include, but are not limited to, diethylsulfamoyl (i.e., N,N-di(methyl)aminosulfonyl).

[0036] As used herein, the term "N,N-di(C1~C4 alkyl)amino" means R a and R b Each of these is a C1-C4 alkyl group as generally defined above, with the formula -N(R a )(R b This refers to the base of ). The term "N,N-di(C1~C3 alkyl)amino" should be interpreted similarly.

[0037] As used herein, the term "C1-C6 alkylsulfanyl" means R a Formula -SR is generally defined as a C1-C6 alkyl group as described above. a This refers to the group. The terms "C1-C4 alkylsulfanyl" and "C1-C3 alkylsulfanyl" should be interpreted similarly. Examples of C1-C6 alkylsulfanyl, though not limited to these, include methylsulfanyl.

[0038] As used herein, the term "C1-C6 alkylsulfinyl" means R a The formula -S(O)R is generally defined as a C1-C6 alkyl group as described above. a This refers to the group. The terms "C1-C4 alkylsulfinyl" and "C1-C3 alkylsulfinyl" should be interpreted similarly. Examples of C1-C6 alkylsulfinyl, though not limited to these, include methylsulfinyl.

[0039] As used herein, the term "C1-C6 alkylsulfonyl" means R a The formula -S(O)2R is generally defined as a C1-C6 alkyl group as described above. a This refers to the group. The terms "C1-C4 alkylsulfonyl" and "C1-C3 alkylsulfonyl" should be interpreted similarly. Examples of C1-C6 alkylsolfanyls, though not limited to these, include methylsulfonyl.

[0040] As used herein, the term "C1-C6 alkylsulfonamide" means R a The formula -NHS(O)2R is generally defined as a C1-C6 alkyl group as described above. a It refers to the base of.

[0041] The presence of one or more possible stereodiene elements in a compound of formula (I) means that the compound can exist in optical isomers, i.e., enantiomers or diastereoisomers. Atropisomers can also arise from the restriction of rotation involving single bonds. Formula (I) is intended to encompass all of these possible isomers and mixtures thereof. The present invention encompasses all of these possible isomers and mixtures thereof relating to compounds of formula (I). Similarly, formula (I) is intended to encompass all possible tautomers. The present invention encompasses all possible tautomers relating to compounds of formula (I).

[0042] In each case, the compound of formula (I) according to the present invention is in free form, oxidized form as an N-oxide, or salt form, for example, an agriculturally usable salt form. It is preferable that the compound of formula (I) can form salts with amines including primary, secondary, and tertiary amines (e.g., ammonia, dimethylamine, and triethylamine), alkali metal and alkaline earth metal bases, transition metals, or quaternary ammonium bases. In a particularly preferred set of embodiments, the compound of formula (I) can form a chloride or a 2,2,2-trifluoroacetate.

[0043] N-oxides are oxidized forms of tertiary amines or nitrogen-containing aromatic heterocyclic compounds. These are described, for example, in the book "Heterocyclic N-oxides" by A. Albini and S. Pietra, CRC Press, Boca Raton (1991).

[0044] The following list refers to compounds of formula (I), with substituents X and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 This document provides definitions (including preferred definitions) relating to these substituents. Any of the definitions described below for any of these substituents may be combined with any of the definitions of any other substituents described below or elsewhere in this document.

[0045] X is O, NR 6 Or S. In one embodiment, X is O or NR 6 In one set of embodiments, X is O. In the other set of embodiments, X is NR 6 In further embodiments of the set, X is S.

[0046] R 1is a C1-C6 alkyl group. Preferably, R 1 is a C1-C4 alkyl group. More preferably, R 1 is a C1-C3 alkyl group. More preferably, R 1 is methyl, ethyl, n-propyl, or isopropyl. More preferably, R 1 is methyl or ethyl. Most preferably, R 1 It is ethyl.

[0047] R 2 is phenyl or heteroaryl, and the heteroaryl moiety is a 5-membered or 6-membered aromatic ring containing 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, and each phenyl and heteroaryl moiety is R 7 It may be arbitrarily substituted with one, two, three, or four elements, which may be identical or different, represented by .

[0048] Preferably, R 2 is a phenyl or heteroaryl (where the heteroaryl portion is a 5-membered or 6-membered aromatic ring containing 1, 2, or 3 heteroatoms individually selected from N, O, and S), and each phenyl and heteroaryl portion is R 7 It may be arbitrarily substituted with one, two, or three identical or different bases represented by .

[0049] Comfortable, R 2 is a phenyl or heteroaryl (where the heteroaryl portion is a 5-membered or 6-membered aromatic ring containing one or two heteroatoms individually selected from N and O), and each phenyl and heteroaryl portion is R 7 It may be arbitrarily substituted with one, two, or three identical or different bases represented by .

[0050] Furthermore, R 2is phenyl or heteroaryl (where the heteroaryl moiety is a 5- or 6-membered aromatic ring containing 1 or 2 heteroatoms individually selected from N and O), and each phenyl and heteroaryl moiety may be optionally substituted with 1 or 2 groups which may be the same or different and are represented by R 7 Furthermore, more preferably, R 2 is phenyl or pyridyl, and each phenyl and pyridyl moiety may be optionally substituted with 1 or 2 groups which may be the same or different and are represented by R 7 In one set of embodiments, R

[0051] In one set of embodiments, R 2 is 4-chlorophenyl, 3,4-dichlorophenyl, 3,4-difluorophenyl, 4-bromo-2-fluorophenyl, 4-bromo-3-fluorophenyl, 3-chloro-4-fluorophenyl, 4-chloro-3-fluorophenyl, 3-chloro-4-nitrophenyl, 4-chloro-3-nitrophenyl, 3-chloro-4-(2,4-difluorophenyl)phenyl, 2-chloro-4-pyridyl, 5-chloro-2-pyridyl, 5,6-dichloro-2-pyridyl or 5,6-dichloro-3-pyridyl. In a further set of embodiments, R 2 is 4-chlorophenyl, 3,4-dichlorophenyl, 3,4-difluorophenyl, 4-bromo-2-fluorophenyl, 4-bromo-3-fluorophenyl, 3-chloro-4-fluorophenyl, 3-chloro-4-(2,4-difluorophenyl)phenyl, 2-chloro-4-pyridyl, 5-chloro-2-pyridyl, 5,6-dichloro-2-pyridyl or 5,6-dichloro-3-pyridyl.

[0052] In another set of embodiments, R 2 is phenyl optionally substituted with 1 or 2 groups, preferably 2 groups which may be the same or different and are represented by R 7 In a further set of embodiments, R 2 is 3,4-dichlorophenyl.

[0053] R 3 is hydrogen, C1-C6 alkyl, N,N-di(C1-C3 alkyl)amino, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, phenyl or phenyl C1-C3 alkyl, and the phenyl moiety may be optionally substituted with 1, 2, 3 or 4 groups which may be the same or different and are represented by R 8 .

[0054] Preferably, R 3 is hydrogen, C1-C6 alkyl, N,N-di(C1-C3 alkyl)amino, C1-C3 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C1-C4 alkoxy C1-C2 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, phenyl or phenyl C1-C2 alkyl, and the phenyl moiety may be optionally substituted with 1, 2 or 3 groups which may be the same or different and are represented by R 8 .

[0055] More preferably, R 3 is hydrogen, C1-C6 alkyl or N,N-di(C1-C3 alkyl)amino, C1-C3 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C1-C4 alkoxy C1-C2 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, phenyl or phenyl C1-C2 alkyl, and the phenyl moiety may be optionally substituted with 1, 2 or 3 groups which may be the same or different and are represented by R 8 .

[0056] In one set of embodiments, R 3 is hydrogen, C1-C6 alkyl, N,N-di(C1-C3 alkyl)amino, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl or phenyl C1-C3 alkyl, and the phenyl moiety may be optionally substituted with 1, 2, 3 or 4 groups which may be the same or different and are represented by R8 It may be arbitrarily substituted with one, two, three, or four elements, which may be identical or different, represented by .

[0057] Preferably, R 3 The C1-C6 alkyl group is hydrogen, C1-C6 alkyl group, N,N-di(C1-C3 alkyl)amino group, C1-C3 haloalkyl group, C3-C6 cycloalkyl group, C3-C6 cycloalkyl group, C1-C3 alkyl group, C1-C4 alkoxy group, C1-C2 alkyl group, C2-C3 alkenyl group, C2-C3 alkynyl group, or phenyl C1-C2 alkyl group, and the phenyl portion is R 8 It may be arbitrarily substituted with one, two, or three identical or different bases represented by .

[0058] Comfortable, R 3 The C1-C6 alkyl group is hydrogen, or N,N-di(C1-C3 alkyl)amino, C1-C3 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C3 alkyl, C1-C4 alkoxyC1-C2 alkyl, C2-C3 alkenyl, C2-C3 alkynyl, or phenyl C1-C2 alkyl, and the phenyl portion is R 8 It may be arbitrarily substituted with one, two, or three identical or different bases represented by .

[0059] In other embodiments, R 3 is hydrogen, C1-C4 alkyl, or N,N-di(C1-C3 alkyl)amino. Preferably, R 3 is hydrogen, C1-C4 alkyl or N,N-di(methyl)amino, more preferably hydrogen, C1-C3 alkyl or N,N-di(methyl)amino. Even more preferably R 3 is hydrogen, methyl, ethyl, or N,N-di(methyl)amino. More preferably, R 3 is hydrogen, methyl, or N,N-di(methyl)amino. More preferably, R 3 It is hydrogen.

[0060] R 4The compounds are C3-C6 cycloalkenyl, phenyl, phenyl C1-C2 alkyl, phenyl C1-C2 alkenyl, heterocyclyl (where the heterocyclyl portion is a 4-membered, 5-membered, or 6-membered non-aromatic monocyclic ring containing 1, 2, or 3 heteroatoms individually selected from N, O, and S), or heteroaryl (where the heteroaryl portion is a 5-membered or 6-membered aromatic monocyclic ring containing 1, 2, or 3 heteroatoms individually selected from N, O, and S), where the phenyl, heterocyclyl, and heteroaryl portions are each R 9 It may be arbitrarily substituted with one, two, three, or four bases, which may be identical or different, represented by; or R 4 This is a 6- to 10-membered cyclocyclic system that optionally contains 1, 2, or 3 heteroatoms individually selected from N, O, and S, and the cyclocyclic system is R 12 The ring may be optionally substituted with one or two groups represented by , and the cyclized ring system may be optionally bonded to the remainder of the molecule via C1-C2 alkylene linkers.

[0061] Preferably, R 4 The compounds are C3-C6 cycloalkenyl, phenyl, phenyl C1-C2 alkyl, phenyl C1-C2 alkenyl, heterocyclyl (where the heterocyclyl portion is a 5-membered or 6-membered non-aromatic monocyclic ring containing one or two heteroatoms individually selected from N, O, and S), or heteroaryl (where the heteroaryl portion is a 5-membered or 6-membered aromatic monocyclic ring containing one, two, or three heteroatoms individually selected from N, O, and S), where the phenyl, heterocyclyl, and heteroaryl portions are each R 9 It may be arbitrarily substituted with one, two, or three bases, which may be identical or different, represented by; or R 4 This is an 8- to 10-membered cyclocyclic system that optionally contains one or two heteroatoms individually selected from N, O, and S, and the cyclocyclic system is R 12The ring may be optionally substituted with one or two groups represented by , and the cyclized ring system may be optionally bonded to the remainder of the molecule via a C1-C2 alkylene linker.

[0062] Comfortable, R 4 The compounds are C4-C6 cycloalkenyls, phenyls, phenyl C1-C2 alkenyls, heterocyclyls (where the heterocyclyl portion is a 6-membered non-aromatic monocyclic ring containing one nitrogen atom), or heteroaryls (where the heteroaryl portion is a 5-membered or 6-membered aromatic monocyclic ring containing one or two heteroatoms individually selected from N, O, and S), where the phenyl and heteroaryl portions are each R 9 The heterocyclyl moiety may be arbitrarily substituted with one, two, or three groups, which may be identical or different, represented by; and each of the heterocyclyl moieties is R 9 It may be arbitrarily substituted with one or two bases, which may be identical or different, represented by; or R 4 It is a 10-membered cyclocyclic system that optionally contains one heteroatom selected from N and O, and the cyclocyclic system is optionally bonded to the remainder of the molecule via a C1-C2 alkylene linker.

[0063] Furthermore, R 4 These are cyclopentenyl, phenyl, styryl, pyridyl, pyrazinyl, pyridadinyl, pyrimidinyl, thienyl, oxazolyl, furyl, or imidazolyl, and the phenyl portion is each R 9 The pyridyl moiety may be optionally substituted with one, two, or three groups, which may be identical or different, and each pyridyl moiety may have R on a carbon or nitrogen atom. 9 The groups may be optionally substituted with one or two identical or different groups represented by , and each pyrimidinyl, thienyl, and imidazolyl moiety may have one R 9 The base may be arbitrarily substituted, or R 4 This is one R 9 A 2-oxo-4-pyridyl group optionally substituted with a group, or R 4This is a quinolyl group.

[0064] In one embodiment, R 4 The compounds are C3-C6 cycloalkenyl, phenyl, phenyl C1-C2 alkyl, phenyl C1-C2 alkenyl, heterocyclyl (where the heterocyclyl portion is a 4-membered, 5-membered, or 6-membered non-aromatic monocyclic ring containing 1, 2, or 3 heteroatoms individually selected from N, O, and S), or heteroaryl (where the heteroaryl portion is a 5-membered or 6-membered aromatic monocyclic ring containing 1, 2, or 3 heteroatoms individually selected from N, O, and S), where the phenyl, heterocyclyl, and heteroaryl portions are each R 9 It may be arbitrarily substituted with one, two, three, or four elements, which may be identical or different, represented by .

[0065] Preferably, R 4 The compounds are C4-C6 cycloalkenyls, phenyls, phenyl C1-C2 alkenyls, heterocyclyls (where the heterocyclyl portion is a 5- or 6-membered non-aromatic monocyclic ring containing one or two heteroatoms individually selected from N, O, and S), or heteroaryls (where the heteroaryl portion is a 5- or 6-membered aromatic monocyclic ring containing one or two heteroatoms individually selected from N, O, and S), where the phenyl, heterocyclyl, and heteroaryl portions are each R 9 It may be arbitrarily substituted with one, two, or three identical or different bases represented by .

[0066] Comfortable, R 4 R is a cyclopentenyl, phenyl, styryl, heterocyclyl (where the heterocyclyl portion is a 6-membered non-aromatic monocyclic ring containing one or two nitrogen atoms), or heteroaryl (where the heteroaryl portion is a 5-membered or 6-membered aromatic monocyclic ring containing one or two heteroatoms individually selected from N, O, and S), where the phenyl, heterocyclyl, and heteroaryl portions are each R 9It may be arbitrarily substituted with one, two, or three identical or different bases represented by .

[0067] Furthermore, R 4 R is a cyclopentenyl, phenyl, styryl, heterocyclyl (where the heterocyclyl portion is a 6-membered non-aromatic monocyclic ring containing one nitrogen atom), or heteroaryl (where the heteroaryl portion is a 5-membered or 6-membered aromatic monocyclic ring containing one or two heteroatoms individually selected from N, O, and S), where the phenyl, heterocyclyl, and heteroaryl portions are each R 9 It may be arbitrarily substituted with one or two bases, which may be identical or different, represented by .

[0068] Furthermore, R 4 R is a phenyl or heteroaryl compound (where the heteroaryl portion is a 5-membered or 6-membered aromatic monocyclic ring containing one or two heteroatoms individually selected from N, O, and S), where the phenyl, heterocyclyl, and heteroaryl portions are each R 9 It may be arbitrarily substituted with one or two bases, which may be identical or different, represented by .

[0069] In a preferred set embodiment, R 4These include cyclopenten-1-yl, phenyl, (E)-styryl, 3-cyanophenyl, 4-cyanophenyl, 4-nitrophenyl, 3-acetylphenyl, 4-acetylphenyl, 2-methylphenyl(o-tolyl), 3-methylphenyl(m-tolyl), 4-methylphenyl(p-tolyl), 4-ethylphenyl, 4-tert-butylphenyl, 2,5-dimethylphenyl, 3,5-dimethylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 3-(difluoromethylphenyl Phenyl, 3-(trifluoromethyl)phenyl, 4-(difluoromethyl)phenyl, 4-(trifluoromethyl)phenyl, 4-methoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 4-(methoxymethyl)phenyl, 3-(trifluoromethoxy)phenyl, 4-(trifluoromethoxy)phenyl, 2,4-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 3,4-dimethoxyphenyl, 3,5-Dimethoxyphenyl, 4-Methoxy-3-methylphenyl, 2-Chloro-5-fluorophenyl, 4-Chloro-2-fluorophenyl, 4-Chloro-3-fluorophenyl, 3-Chloro-5-fluorophenyl, 5-Chloro-2-fluorophenyl, 4-Chloro-3-cyanophenyl, 3-cyano-4-fluorophenyl, 3-cyano-5-fluorophenyl, 3-cyano-5-methylphenyl, 4-cyano-3-ethoxyphenyl, 4-cyano-3-(trifluoromethyl)phenyl, 2-fluoro-3-methylphenyl, 2-Fluoro-4-methylphenyl, 4-Fluoro-3-methylphenyl, 2-Fluoro-5-methylphenyl, 5-Fluoro-2-methylphenyl, 4-Chloro-3-ethylphenyl, 4-Chloro-3-(ethylcarbamoyl)phenyl, 2-Fluoro-3-(trifluoromethyl)phenyl, 2-Fluoro-5-(trifluoromethyl)phenyl, 3-methyl-5-(trifluoromethyl)phenyl, 2-Chloro-5-(trifluoromethyl)phenyl, 3-Chloro-4-(trifluoromethyl)phenyl, 3-Chloro-5-(trifluoro Methylphenyl, 3-chloro-4-(trifluoromethyl)phenyl, 4-chloro-3-(trifluoromethyl)phenyl, 2-chloro-5-(trifluoromethoxy)phenyl, 3-(2,2,2-trifluoroethoxy)phenyl, 3-fluoro-5-(2,2,2-trifluoroethoxy)phenyl, 4-fluoro-3-(2,2,2-trifluoroethoxy)phenyl, 2-fluoro-3-methoxyphenyl, 2-fluoro-5-methoxyphenyl, 3-chloro-4-methoxyphenyl, 3-fluoro-4-methoxyphenyl, 3-fluorophenyl Oro-5-methoxyphenyl, 4-fluoro-2-methoxyphenyl, 5-fluoro-2-methoxyphenyl, 4-chloro-2-methoxyphenyl, 4-chloro-3-ethoxyphenyl, 3-ethoxy-5-fluorophenyl, 4-methoxy-3-(trifluoromethyl)phenyl, 3-ethoxy-5-methylphenyl, 4-fluoro-2-methylphenyl, 4-chloro-2-methylphenyl, 4-chloro-2-methylsulfanylphenyl, 4-chloro-3-nitrophenyl, 3,4-bis(trifluoromethyl)phenyl, 3,5-Bis(trifluoromethyl)phenyl, 4-Cyano-2-methylphenyl, 4-Cyano-2-methylsulfanylphenyl, 4-(dimethylcarbamoyl)phenyl, 4-Chloro-3-(cyclopropylcarbamoyl)phenyl, 3-Methylsulfanylphenyl, 4-Methylsulfanylphenyl, 4-Methylsulfonylphenyl, 4-Ethylsulfonylphenyl, 2-Fluoro-4-methylsulfonylphenyl, 4-(diethylsulfamoyl)phenyl, 3-Phenoxyphenyl, 4-Benzyloxyphenyl, 3-Ethoxy-4-(trifluoromethyl)phenyl, 3-Ethoxy-5-(trifluoromethyl)phenyl, 3,4,5-Trifluorophenyl, 4-Chloro-3,5-dimethylphenyl, 3-Chloro-4-Fluoro-5-Methoxyphenyl, 3-Chloro-4,5-Dimethoxyphenyl, 3-Chloro- 5-Fluoro-4-methoxyphenyl, 4-methoxy-3,5-dimethylphenyl, 2,4-difluoro-3-methylphenyl, 2,4-difluoro-3-methoxyphenyl, 3,5-difluoro-4-methoxyphenyl, 3,5-dichloro-4-fluorophenyl, 4-fluoro-3,5-dimethylphenyl, 5-tert-butoxycarbonyl-4-chloro-2-fluorophenyl, 4-chloro-2-fluoro-5-(2-methoxyethoxy)phenyl, 4-chloro-2-fluoro-5-isopropoxyphenyl, 4-chloro-5-(cyclopropylmethoxy)-2-fluorophenyl, 4-chloro-2-fluoro-5-methoxycarbonylphenyl, 1-cyanocyclopropyl)-2-fluorophenyl, 2,2-difluoro-1,3-benzodioxol-4-yl, 1-methylpyrazole-4-yl, 2,5-dimethylpyrazole-3-yl, 2-methylpyrazole-3-yl, 3-methylimidazole-4-yl, 3-pyridyl, pyridine-1-ium-2-yl, pyridine-1-ium-3-yl, pyridine-1-ium-4-yl, 2-fluoro-3-pyridyl, 6-fluoro-3-pyridyl, 5-chloro-3-pyridyl, 6-chloro-3-pyridyl, 2-fluoro-4-pyridyl, 6-fluoro-2-methyl-3-pyridyl, 6-(trifluoromethyl)-2-pyridyl, 6-(trifluoromethyl)-3-pyridyl, 2-chloro-6-isopropoxy-4-pyridyl, 5-chloro-2-fluoro-3-pyridyl, 6-chloro-5-methyl-3-pyridyl, 2-methoxy-4-pyridyl, 5-methoxy-3-pyridyl, 6-methoxy-2-pyridyl, 6 -Methoxy-3-pyridyl, 5,6-dichloro-3-pyridyl, 5,6-difluoro-3-pyridyl, 2,6-dimethoxy-3-pyridyl, 5-methylsulfonyl-3-pyridyl, 4-(methanesulfonamide)phenyl, 1-methyl-2-oxo-4-pyridyl, 2,2-difluoro-[1,3]dioxolo[4,5-b]pyridin-6-yl, pyrazine-2-yl, pyridazine-4-yl, pyridazine-1-ium-4-yl, pyrimidine-5-yl, 2-chloropyrimidine-5-yl, 2-(trifluoromethyl)pyrimidine-5-yl, 2-thienyl, 3-thienyl, 4-methyl-2-thienyl, 4-methyl-3-thienyl, 5-chloro-2-thienyl, 5-chloro-3-thienyl, oxazole-2-yl, 3-furyl, or 2-quinolyl.

[0070] In a particularly preferred set embodiment, R 4These include cyclopenten-1-yl, phenyl, 3-cyanophenyl, 4-cyanophenyl, 4-nitrophenyl, 3-acetylphenyl, 4-acetylphenyl, 2-methylphenyl(o-tolyl), 4-ethylphenyl, 4-tert-butylphenyl, 2,5-dimethylphenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-fluorophenyl, 4-fluorophenyl, 3-(difluoromethyl)phenyl, 3-(trifluoromethyl)phenyl, 4-(difluoromethyl)phenyl, and 4-(trifluoromethyl) Phenyl, 4-methoxyphenyl, 4-ethoxyphenyl, 4-(methoxymethyl)phenyl, 3-(trifluoromethoxy)phenyl, 4-(trifluoromethoxy)phenyl, 2,4-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 3,4-dimethoxyphenyl, 3,5-dimethoxyphenyl, 4-methoxy-3-methylphenyl, 2-chloro-5-fluorophenyl, 4-chloro- 3-Fluorophenyl, 3-Chloro-5-Fluorophenyl, 5-Chloro-2-Fluorophenyl, 4-Chloro-3-Cyanophenyl, 3-Cyano-4-Fluorophenyl, 3-Cyano-5-Fluorophenyl, 3-Cyano-5-Methylphenyl, 4-Cyano-3-Ethoxyphenyl, 4-Cyano-3-(Trifluoromethyl)phenyl, 2-Fluoro-3-Methylphenyl, 2-Fluoro-4-Methylphenyl, 2-Fluoro-5-Methylphenyl, 5-Fluoro-2-Methylphenyl, 4-Chloro-3-(Ethyl Rubamoyl)phenyl, 2-fluoro-3-(trifluoromethyl)phenyl, 2-fluoro-5-(trifluoromethyl)phenyl, 3-methyl-5-(trifluoromethyl)phenyl, 2-chloro-5-(trifluoromethyl)phenyl, 3-chloro-4-(trifluoromethyl)phenyl, 3-chloro-5-(trifluoromethyl)phenyl, 3-chloro-4-(trifluoromethyl)phenyl, 2-chloro-5-(trifluoromethoxy)phenyl, 3-(2,2,2-trifluoroethoxy)phenyl, 3-fluoro-5-(2,2,2-trifluoroethoxy)phenyl, 4-fluoro-3-(2,2,2-trifluoroethoxy)phenyl, 2-fluoro-3-methoxyphenyl, 2-fluoro-5-methoxyphenyl, 3-chloro-4-methoxyphenyl, 3-fluoro-4-methoxyphenyl, 4-fluoro-2-methoxyphenyl, 5-fluoro-2-methoxyphenyl, 4-chloro-2-methoxyphenyl, 4-methoxy-3-(trifluoromethyl)phenyl, 3-ethoxy-5-methylphenyl, 4-fluoro-2-methylphenyl, 4-chloro-2-methylphenyl, 4-chloro-2-methylsulfanylphenyl, 4-(dimethylcarbamoyl)phenyl, 4-chloro-3-(cyclopropylcarbamoyl)phenyl, 3-methylsulfanylphenyl, 4-methylsulfanylphenyl, 4-methylsulfonylphenyl, 4-ethylsulfonylphenyl, 2-fluoro-4-methylsulfonylphenyl, 4-(diethyl Sulfamoyl)phenyl, 3-phenoxyphenyl, 4-benzyloxyphenyl, 3-ethoxy-4-(trifluoromethyl)phenyl, 3-ethoxy-5-(trifluoromethyl)phenyl, 3,4,5-trifluorophenyl, 4-chloro-3,5-dimethylphenyl, 3-chloro-4,5-dimethoxyphenyl, 3-chloro-5-fluoro-4-methoxyphenyl, 4-methoxy-3,5-dimethylphenyl, 2,4-difluoro-3-methoxy -phenyl, 3,5-difluoro-4-methoxyphenyl, 3,5-dichloro-4-fluorophenyl, 4-fluoro-3,5-dimethylphenyl, 4-chloro-2-fluoro-5-(2-methoxyethoxy)phenyl, 4-chloro-2-fluoro-5-isopropoxyphenyl, 4-chloro-5-(cyclopropylmethoxy)-2-fluorophenyl, 2,2-difluoro-1,3-benzodioxol-4-yl, 1-methylpyrazole-4-yl, 2,5-dimethylpyrazole-3-yl, 2-methylpyrazole-3-yl, 3-methylimidazole-4-yl, 3-pyridyl, pyridine-1-ium-2-yl, pyridine-1-ium-3-yl, pyridine-1-ium-4-yl, 2-fluoro-3-pyridyl, 6-fluoro-3-pyridyl, 5-chloro-3-pyridyl, 6-chloro-3-pyridyl, 2-fluoro-4-pyridyl, 6-(trifluoromethyl)-2-pyridyl, 6-(trifluoromethyl)-3-pyridyl, 2-chloro-6-isopropoxy-4-pyridyl, 6-chloro-5-methyl-3 -Pyridyl, 2-methoxy-4-pyridyl, 5-methoxy-3-pyridyl, 6-methoxy-2-pyridyl, 6-methoxy-3-pyridyl, 1-methyl-2-oxo-4-pyridyl, 2,2-difluoro-[1,3]dioxolo[4,5-b]pyridin-6-yl, pyrazine-2-yl, pyridazin-4-yl, pyridazin-1-ium-4-yl, 2-thienyl, 3-thienyl, 4-methyl-2-thienyl, 4-methyl-3-thienyl, 5-chloro-2-thienyl, 5-chloro-3-thienyl, oxazole-2-yl, 3-furyl, or 2-quinolyl.

[0071] R 5 is a halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, or C1-C4 alkoxy C1-C4 alkyl. Preferably, R 5 is a C1-C4 alkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, or C1-C3 alkoxy C1-C2 alkyl. More preferably, R 5 is a C1-C4 alkyl or a C1-C2 alkoxy C1-C2 alkyl. Further, R 5 is a C1-C3 alkyl or a C1-C2 alkoxy C1-C2 alkyl. In one embodiment, R 5 It is methyl or methoxymethyl.

[0072] In a particular set of embodiments, R 5 is a C1-C3 alkyl, a C1-C3 haloalkyl, or a C1-C2 alkoxy C1-C2 alkyl. Preferably, R5 is a C1-C3 alkyl, a C1-C2 haloalkyl, or a C1-C2 alkoxy C1-C2 alkyl. More preferably, R 5 These are methyl, methoxymethyl, methoxyethyl, bromomethyl, or difluoromethyl.

[0073] R 6 R is hydrogen, a C1-C3 alkyl group, or a C1-C6 alkoxy group. Preferably, 6 R is hydrogen or a C1-C3 alkyl group. More preferably, 6 is hydrogen, methyl, or ethyl. More preferably, R 6 It is hydrogen.

[0074] R 7 The compounds are cyano, nitro, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 alkoxyC1-C6 alkyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonamide, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl, N,N-di(C1-C4 alkyl)aminocarbonyl, or phenyl, and each phenyl portion is R 10 It may be optionally substituted with one, two, or three groups, which may be the same or different, represented by . Preferably, R 7 The compounds are cyano, nitro, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C3 alkoxy, C1-C3 alkyl, C1-C4 alkyl sulfanyl, C1-C4 alkyl sulfinyl, C1-C4 alkyl sulfonyl, C1-C4 alkyl sulfonamide, C1-C4 alkyl carbonyl, C1-C4 alkoxycarbonyl, C1-C4 alkylaminocarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl, N,N-di(C1-C3 alkyl)aminocarbonyl, or phenyl, and each phenyl portion is R10 It may be optionally substituted with one or two groups, which may be the same or different, represented by . More preferably, R 7 The compounds are cyano, nitro, halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C3 alkoxy, C1-C3 alkyl, C1-C3 alkyl sulfanyl, C1-C3 alkyl sulfinyl, C1-C3 alkyl sulfonyl, C1-C3 alkyl sulfonamide, C1-C3 alkyl carbonyl, C1-C3 alkoxy carbonyl, C1-C3 alkylaminocarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl, N,N-di(C1-C3 alkyl)aminocarbonyl, or phenyl, and each phenyl portion is R 10 It may be optionally substituted with one or two groups, which may be the same or different, represented by . More preferably, R 7 The compounds are cyano, nitro, halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C3 alkoxy, C1-C3 alkyl, C1-C3 alkylsulfanyl, C1-C3 alkylsulfonyl, C1-C2 alkylcarbonyl, C1-C3 alkoxycarbonyl, N,N-di(C1-C2 alkyl)aminocarbonyl, or phenyl, and each phenyl portion is R 10 It may be arbitrarily substituted with one or two bases, which may be identical or different, represented by .

[0075] In one embodiment, R 7 is nitro, halogen, or phenyl, and each phenyl portion is R 10 It may be optionally substituted with one or two groups, which may be the same or different, represented by . Preferably, R 7 is a halogen or phenyl, and each phenyl portion is R 10 It may be optionally substituted with one or two groups, which may be the same or different, represented by . More preferably, R 7 is chloro, fluoro, bromo, or phenyl, and each phenyl portion is R 10It may be optionally substituted with two identical or different groups represented by . More preferably, R 7 These are chloro, fluoro, bromo, or 2,4-difluorophenyl.

[0076] R 8 is a halogen, cyano, C1-C3 alkyl, or C1-C3 alkoxy. Preferably, R 8 is a halogen, cyano, methyl, ethyl, methoxy, or ethoxy. More preferably, R 8 These are chloro, bromo, fluoro, methyl, or methoxy compounds.

[0077] R 9 These include cyano, nitro, halogen, oxo, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1- C6 alkylsulfonamide, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkoxy, N,N-di(C1-C4 alkyl)aminosulfonyl, C3-C6 cycloalkylaminocarbonyl, N,N-di(C1-C4 alkyl)aminocarbonyl, phenoxy or benzyloxy, where each cycloalkyl or phenyl portion is R 12 It may be arbitrarily substituted with one or two bases, which may be identical or different, represented by; or Any two adjacent R 9 The groups, together with the carbon atoms to which they are bonded, can form a five-membered or six-membered heterocyclyl ring containing one or two heteroatoms selected from O and N, and the heterocyclyl ring is R 11 It may be arbitrarily substituted with one, two, three, or four elements, which may be identical or different, represented by .

[0078] Preferably, R 9 These are cyano, nitro, halogen, oxo, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylsulfanyl, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonamide, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, N,N-di(C1-C4 alkyl)aminosulfonyl, C3-C6 cycloalkylaminocarbonyl, N,N-di(C1-C4 alkyl)aminocarbonyl, phenoxy, or benzyloxy, and each cycloalkyl or phenyl portion is R 12 It may be arbitrarily substituted with one or two bases, which may be identical or different, represented by; or Any two adjacent R 9 The groups, together with the carbon atoms to which they are bonded, can form a five-membered or six-membered heterocyclyl ring containing one or two heteroatoms selected from O and N, and the heterocyclyl ring is R 11 It may be arbitrarily substituted with one, two, or three identical or different bases represented by .

[0079] Comfortable, R 9These are cyano, nitro, halogen, oxo, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfonyl, C1-C4 alkylsulfonamide, C1-C4 alkylcarbonyl, C1-C4 alkoxycarbonyl, C3-C4 cycloalkyl, C3-C4 cycloalkyl, C1-C3 alkoxy, N,N-di(C1-C3 alkyl)aminosulfonyl, C3-C4 cycloalkylaminocarbonyl, N,N-di(C1-C3 alkyl)aminocarbonyl, phenoxy, or benzyloxy, and each cycloalkyl or phenyl portion is R 12 It may be arbitrarily substituted with one or two bases, which may be identical or different, represented by; or Any two adjacent R 9 The groups, together with the carbon atoms to which they are bonded, can form a five-membered or six-membered heterocyclyl ring containing one or two heteroatoms selected from O and N, and the heterocyclyl ring is R 11 It may be arbitrarily substituted with one or two bases, which may be identical or different, represented by .

[0080] Furthermore, R 9 These are cyano, nitro, halogen, oxo, C1-C4 alkyl, C1-C3 alkoxy, C1-C2 haloalkyl, C1-C2 haloalkoxy, C1-C2 alkoxy, C1-C2 alkyl, C1-C2 alkoxy, C1-C3 alkylsulfanyl, C1-C3 alkylsulfonyl, C1-C3 alkylsulfonamide, C1-C2 alkylcarbonyl, C1-C4 alkoxycarbonyl, cyclopropyl, cyclopropyl C1-C2 alkoxy, N,N-di(C1-C2 alkyl)aminosulfonyl, cyclopropylaminocarbonyl, N,N-di(C1-C2 alkyl)aminocarbonyl, phenoxy, or benzyloxy, and each cycloalkyl or phenyl portion is R 12 It may be optionally substituted with a single base represented by; or Any two adjacent R 9 The groups, together with the carbon atoms to which they are bonded, can form a five-membered heterocyclyl ring containing two oxygen atoms, where the heterocyclyl ring is R 11 It may be arbitrarily substituted with one or two bases, which may be identical or different, represented by .

[0081] Furthermore, R 9 These include cyano, nitro, chloro, fluoro, oxo, methyl, ethyl, t-butyl, methoxy, ethoxy, isopropoxy, difluoromethyl, trifluoromethyl, trifluoromethoxy, 2,2,2-trifluoroethoxy, methoxymethyl, methoxyethoxy, methylsulfanyl, methylsulfonyl, ethylsulfonyl, methylsulfonamide, acetyl(methylcarbonyl), methoxycarbonyl, tert-butoxycarbonyl, R 12 Cyclopropyl, cyclopropylmethoxy, ethylcarbamoyl (ethylaminocarbonyl), dimethylcarbamoyl (N,N-di(methyl)aminocarbonyl), cyclopropylcarbamoyl (cyclopropylaminocarbonyl), diethylsulfamoyl (N,N-di(methyl)aminosulfonyl), phenoxy or benzyloxy, which may be optionally substituted with a single group represented by ; or any two adjacent R 9 The groups, together with the carbon atoms to which they are bonded, may form a five-membered heterocyclyl ring containing two oxygen atoms, and the heterocyclyl ring may be optionally substituted with one or two fluoro groups.

[0082] Furthermore, R 9These are cyano, nitro, chloro, fluoro, oxo, methyl, t-butyl, methoxy, ethoxy, isopropoxy, difluoromethyl, trifluoromethyl, trifluoromethoxy, 2,2,2-trifluoroethoxy, methoxymethyl, methoxyethoxy, methylsulfanyl, methylsulfonyl, ethylsulfonyl, acetyl(methylcarbonyl), cyclopropylmethoxy, ethylcarbamoyl(ethylaminocarbonyl), cyclopropylcarbamoyl(cyclopropylaminocarbonyl), dimethylcarbamoyl(N,N-di(methyl)aminocarbonyl), diethylsulfamoyl(N,N-di(methyl)aminosulfonyl), phenoxy, benzyloxy; or any two adjacent R 9 The groups, together with the carbon atoms to which they are bonded, may form a five-membered heterocyclyl ring containing two oxygen atoms, and the heterocyclyl ring may be optionally substituted with one or two fluoro groups.

[0083] In one embodiment, R 9 is cyano, nitro, halogen, oxo, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 alkoxyC1-C6 alkyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonamide, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl, N,N-di(C1-C4 alkyl)aminocarbonyl or benzyloxy; or Any two adjacent R 9 The groups, together with the carbon atoms to which they are bonded, can form a five-membered or six-membered heterocyclyl ring containing one or two heteroatoms selected from O and N, and the heterocyclyl ring is R 11 It may be arbitrarily substituted with one, two, three, or four elements, which may be identical or different, represented by .

[0084] Preferably, R 9is cyano, nitro, halogen, oxo, C1-C6 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxyC1-C4 alkyl, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylsulfonamide, C1-C4 alkylcarbonyl, C1-C4 alkoxycarbonyl, C1-C4 alkylaminocarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl, N,N-di(C1-C3 alkyl)carbonyl or benzyloxy; or any two adjacent R 9 The groups, together with the carbon atoms to which they are bonded, can form a five-membered or six-membered heterocyclyl ring containing one or two heteroatoms selected from O and N, and the heterocyclyl ring is R 11 It may be arbitrarily substituted with one, two, or three identical or different bases represented by .

[0085] Comfortable, R 9 is cyano, nitro, halogen, oxo, C1-C6 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxyC1-C4 alkyl, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylsulfonamide, C1-C4 alkylcarbonyl, C1-C4 alkylaminocarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl, N,N-di(C1-C3 alkyl)carbonyl or benzyloxy; or any two adjacent R 9 The groups, together with the carbon atoms to which they are bonded, can form a five-membered or six-membered heterocyclyl ring containing one or two heteroatoms selected from O and N, and the heterocyclyl ring is R 11 It may be arbitrarily substituted with one, two, or three identical or different bases represented by .

[0086] Furthermore, R 9is cyano, nitro, halogen, oxo, C1-C4 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, C1-C3 alkoxyC1-C2 alkyl, C1-C3 alkylsulfanyl, C1-C3 alkylsulfonyl, C1-C3 alkylsulfonamide, C1-C3 alkylcarbonyl, C1-C3 alkylaminocarbonyl, C3-C4 cycloalkylaminocarbonyl, N,N-di(C1-C2 alkyl)carbonyl or benzyloxy; or any two adjacent R 9 The groups, together with the carbon atoms to which they are bonded, can form a five-membered heterocyclyl ring containing one or two heteroatoms selected from O and N, and the heterocyclyl ring is R 11 It may be arbitrarily substituted with one or two bases, which may be identical or different, represented by .

[0087] Furthermore, R 9 is nitro, halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, C1-C3 alkylsulfonyl or benzyloxy. More preferably, R 9 These are nitro, chloro, fluoro, methyl, methoxy, trifluoromethyl, trifluoromethoxy, methylsulfonyl, or benzyloxy.

[0088] R 10 is a halogen, a C1-C3 alkyl, or a C1-C3 alkoxy. Preferably, R 10 is a halogen, methyl, or methoxy. More preferably, R 10 is a halogen. More preferably, R 10 is chloro or fluoro. More preferably, R 10 It is fluoro.

[0089] R 11 is a halogen, a C1-C3 alkyl, or a C1-C3 alkoxy. Preferably, R 11 is a halogen, methyl, or methoxy. More preferably, R 11is a halogen. More preferably, R 11 is chloro or fluoro. More preferably, R 11 It is fluoro.

[0090] R 12 is a cyano, halogen, C1-C3 alkyl, or C1-C3 alkoxy. Preferably, R 12 is cyano, halogen, methyl, ethyl, methoxy, ethoxy, or isopropoxy. More preferably, R 12 is cyano or halogen. More preferably, R 12 It is cyano.

[0091] In the compound of formula (I) according to the present invention, preferably: X is O or NR 6 and; R 1 is methyl or ethyl; R 2 It is 3,4-dichlorophenyl; R 3 These are hydrogen, C1-C4 alkyl, or N,N-di(C1-C3 alkyl)amino; R 4 The compounds are C3-C6 cycloalkenyl, phenyl, phenyl C1-C2 alkyl, phenyl C1-C2 alkenyl, heterocyclyl (where the heterocyclyl portion is a 4-membered, 5-membered, or 6-membered non-aromatic monocyclic ring containing 1, 2, or 3 heteroatoms individually selected from N, O, and S), or heteroaryl (where the heteroaryl portion is a 5-membered or 6-membered aromatic monocyclic ring containing 1, 2, or 3 heteroatoms individually selected from N, O, and S), where the phenyl, heterocyclyl, and heteroaryl portions are each R 9 It may be arbitrarily substituted with one, two, three, or four bases, which may be identical or different, represented by; R 5 These are C1-C4 alkyl or C1-C2 alkoxy C1-C2 alkyl; R 6 is hydrogen or a C1-C3 alkyl group; R 7 It is a halogen; R 9 is cyano, nitro, halogen, oxo, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 alkoxyC1-C6 alkyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonamide, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylaminocarbonyl, N,N-di(C1-C4 alkyl)aminocarbonyl or benzyloxy; or Any two adjacent R 9 The groups, together with the carbon atoms to which they are bonded, can form a five-membered or six-membered heterocyclyl ring containing one or two heteroatoms selected from O and N, and the heterocyclyl ring is R 11 It may be arbitrarily substituted with one, two, three, or four bases, which may be identical or different, represented by; and R 11 It is a halogen.

[0092] In the implementation of other groups, X is O or NR 6 and; R 1 is methyl or ethyl; R 2 It is 3,4-dichlorophenyl; R 3 These are hydrogen, C1-C4 alkyl, or N,N-di(C1-C3 alkyl)amino; R 4 R is a phenyl or heteroaryl compound (where the heteroaryl portion is a 5-membered or 6-membered aromatic monocyclic ring containing one or two heteroatoms individually selected from N, O, and S), where the phenyl, heterocyclyl, and heteroaryl portions are each R 9 It may be arbitrarily substituted with one or two bases, which may be identical or different, represented by; R 6 is hydrogen; R 7 is a halogen; and R 9 These are nitro, halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, C1-C3 haloalkoxy, C1-C3 alkylsulfonyl, or benzyloxy.

[0093] The compounds of the present invention can be formed as shown in the following scheme, where, unless otherwise specified, the definition of each variable element is as defined above for the compound of formula (I). A general method for producing the compound of formula (I) is described below. Unless otherwise specified in the text, R 1 , R 2 , R 3 , R 4 , R 5 And X are as already defined herein. The starting materials used in the preparation of the compounds of the present invention may be purchased from ordinary commercial suppliers or prepared by known methods. The starting materials and intermediates may be purified by state-of-the-art techniques such as chromatography, crystallization, distillation and filtration before being used in the next step.

[0094] Scheme 1: [ka] X is NH, and R 3 The compound of formula (I), in which is -N(CH3)2, is prepared in a suitable solvent (such as dichloromethane or ethyl acetate) with an optional additive (such as dimethylaminopyridine), and with a coupling agent such as 1,1-dimethylhydrazine and propylphosphonic anhydride (used undiluted or as a solution in ethyl acetate), wherein X is O and R 3 Compounds of formula (I) can be prepared by coupling, where is hydrogen. This is shown in scheme 1 above. Compounds of formula (I) can also be prepared by the following methods.

[0095] Scheme 2: [ka] X is O, and R 3 Compounds of formula (I) in which is hydrogen are prepared by fermenting a suitable base (such as sodium hydroxide or lithium hydroxide) or a suitable acid (such as trifluoroacetic acid, hydrochloric acid, formic acid or sulfuric acid) in a suitable solvent (such as methanol, ethanol, dichloromethane, chloroform, ethyl acetate or tetrahydrofuran) with any co-solvent (such as water), thereby achieving the compound of formula (I) (wherein X is O and R 3 It is not hydrogen, but any of the other R defined above. 3 It can be prepared by hydrolysis of the group. When a base was used, the product was obtained after acidification with a suitable acid (such as hydrochloric acid). 4 If is pyridyl or pyridazinyl, the product was obtained as an equivalent salt (such as hydrochloride). This is shown in Scheme 2 above. Compounds of formula (I) may be further prepared by the following methods.

[0096] Scheme 3: [ka] R 4Compounds of formula (I) in which is phenyl or heteroaryl can be further prepared from compounds of formula (B) in which Y is Cl, Br or I, via a Suzuki-Miyaura cross-coupling reaction under standard literature conditions. Typically, the reaction is carried out in the presence of a suitable catalyst (such as dichlorobis(triphenylphosphine)palladium(II), tetrakis(triphenylphosphine)palladium, tris(dibenzylideneacetone)dipalladium, or dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct) or palladium diacetate (optionally accompanied by a ligand (such as 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl)), in the presence of a base (such as potassium carbonate or cesium or tripotassium phosphate), in a suitable organic solvent (such as 1,4-dioxane, toluene or tetrahydrofuran), optionally in the presence of water, at high temperature, and R 4 -This is carried out by the reaction of a compound of formula (B) with a boronic acid or boroxine. This is shown in scheme 3 above.

[0097] The compound of formula (I) (wherein X is O and R 3 is hydrogen, and R 4 In the case where ( is pyridinyl or pyridazinyl), the product can also be obtained as a salt (usually trifluoroacetate or hydrochloride).

[0098] In an alternative transformation, the compound of formula (B) where Y is I reacts with R in a suitable solvent (such as toluene) in the presence of a catalyst (such as tetrakis(triphenylphosphine)palladium(O)) at a high temperature (e.g., 120°C) under Still conditions, for example, with a heterocyclic stanane. 4 It can be converted into a compound of formula (I) in which is a C-bonded heterocycle (such as oxazole-2-yl).

[0099] Scheme 4: [ka] Compound of formula (B) (wherein X is O and R 3(wherein X is hydrogen and Y is Br or I) is dissolved in a suitable solvent (such as methanol, ethanol, dichloromethane, chloroform, ethyl acetate, or tetrahydrofuran) with a suitable base (such as sodium hydroxide or lithium hydroxide) or a suitable acid (such as trifluoroacetic acid, hydrochloric acid, formic acid, or sulfuric acid) with any co-solvent (such as water) to form a compound of formula (B) (wherein X is O and R 3 It is not hydrogen, but any of the other R defined above. 3 It can be prepared by hydrolysis of the group. This is shown in scheme 4 above.

[0100] Scheme 5: [ka] Compounds of formula (B), where Y is Br or I, can be prepared by treating compounds of formula (C) with a suitable halogenating agent (such as N-iodohalosuccinimide or N-bromohalosuccinimide) in a suitable solvent (such as acetonitrile or trifluoroacetic acid). This is shown in scheme 5 above.

[0101] Scheme 6: [ka] Y is I, and R 5 Compounds of formula (B) in which Y is a methyl alkoxide can be prepared by the reaction of a compound of formula (D) in which Y is I with an alkoxide base (such as sodium methoxide) in the presence of an alcohol (such as methanol). This is shown in scheme 6 above.

[0102] Scheme 7: [ka] The compound of formula (D) where Y is I is R in a suitable solvent (such as acetonitrile) with an additional acid (such as trifluoroacetic acid) and a suitable iodinating agent (such as N-iodosuccinimide). 5This can be prepared by processing a compound of formula (C) in which is methyl. This is shown in scheme 7 above.

[0103] Scheme 8: [ka] The compound of formula (C), where X is O, can be prepared by reacting the compound of formula (E) with the compound of formula (F) at a high temperature (e.g., 120°C) without the use of a solvent. The compound of formula E is commercially available or can be prepared by methods known to those skilled in the art. This is shown in scheme 8 above.

[0104] Scheme 9: [ka] Compound (F) can be prepared by the reaction of a β-ketoester of formula (G) with an amine salt. The amine salt can be prepared by acidifying the amine of formula (H) in situ with a suitable acid (such as acetic acid). These amine salts can then be reacted with compound (G) in a suitable solvent (such as toluene) in the presence of an acid (such as acetic acid) and a drying agent (such as a 4 Å molecular sieve). Compound (G) is commercially available or can be prepared using the conditions described below. Compound (H) is commercially available or can be prepared by methods known to those skilled in the art. This is shown in Scheme 9 above.

[0105] Scheme 10: [ka] The compound of formula (G) can be prepared by treating the ketone of formula (i) with a base (such as sodium hydride) in the presence of the dialkyl carbonate of formula (J) (such as dimethyl carbonate). The compounds of formula (i) and formula (J) are commercially available or can be prepared by methods known to those skilled in the art. This is shown in scheme 10 above.

[0106] Scheme 11: [ka] Compound of formula (A) (wherein X is O and R 3 It is not hydrogen, but any of the other R defined above. 3 The group is the compound of formula (K) and the compound of formula (F) (wherein R 3 It is not hydrogen, but any other R 3 It can be prepared by reacting the group with the solvent at a high temperature (e.g., 120°C). This is shown in scheme 11 above.

[0107] Scheme 12: [ka] R 4 Compounds of formula (K) where Y is phenyl can be prepared by the reaction of compounds of formula (L) where Y is I under Suzuki-Miyaura cross-coupling conditions similar to those in the literature. Typically, this reaction is carried out in the presence of a suitable catalyst (such as dichlorobis(triphenylphosphine)palladium(II), tetrakis(triphenylphosphine)palladium, tris(dibenzylideneacetone)dipalladium, or dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct) or palladium diacetate (optionally accompanied by a ligand (such as 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl)), in the presence of a base (such as potassium carbonate or cesium or tripotassium phosphate), in a suitable organic solvent (such as 1,4-dioxane, toluene or tetrahydrofuran), optionally in the presence of water, at high temperature, and R 4 -This is carried out by the reaction of a compound of formula (K) with a boronic acid or boroxine. This is shown in scheme 12 above.

[0108] Scheme 13: [ka] Compounds of formula (L), where Y is Br or I, can be prepared by treating a compound of formula (E) with a suitable halogenating agent (such as N-iodohaloxxinimide or N-bromohaloxxinimide) in a suitable solvent (such as acetonitrile, acetic acid, or trifluoroacetic acid). Compounds of formula (E) are commercially available or can be prepared by methods known to those skilled in the art. This is shown in scheme 13 above.

[0109] The present invention further provides a method for controlling weeds in a habitat, the method comprising the application of a composition containing a compound of formula (I) to the habitat in a weed-controlling amount. Furthermore, the present invention may further provide a method for selectively controlling weeds in a habitat containing useful (crop) plants and weeds, the method comprising the application of a composition according to the present invention to the habitat in a weed-controlling amount. "Control" means eradication, reduction or inhibition of growth, or prevention or reduction of germination. It should be noted that the compounds of the present invention exhibit considerably improved selectivity compared to known structurally similar compounds. Generally, the plants to be controlled are unwanted plants (weeds). "Habitat" means an area where plants are growing or will grow. Application may be carried out on the habitat before and / or after the germination of crop plants. Some crop plants may be innately resistant to the herbicidal effect of the compound of formula (I).

[0110] The application rate of the compound of formula (I) can vary within a wide range of limits and depends on soil properties, application method (before or after germination; seed coating; application to sowing furrows; no tillage application, etc.), crop plants, weeds to be controlled, prevailing weather conditions, and other factors that depend on the application method, timing, and target crop. The compound of formula I according to the present invention is generally applied in amounts of 10 to 2500 g / ha, particularly 25 to 1000 g / ha, and especially 25 to 250 g / ha.

[0111] Application is generally carried out by spraying the composition, typically using a large-area sprayer mounted on a tractor, but other methods such as dusting (in the case of powder), dripping, or drenching are also available.

[0112] The term "useful plants" should also be understood to include useful plants in which resistance to herbicides such as bromoxynil, or to certain classifications of herbicides such as 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, ALS inhibitors, e.g., primisulfuron, prosulfuron, and trifloxysulfuron, 5-enol-pyrovir-sikimate-3-phosphate synthase (EPSPS) inhibitors, glutamine synthetase (GS) inhibitors, or protoporphyrinogen oxidase (PPO) inhibitors has been acquired through conventional hybridization or genetic engineering methods. An example of a crop in which resistance to imidazolinones, such as imazamox, has been acquired through conventional hybridization methods (mutaogenesis) is Clearfield® summer rapeseed (canola). Examples of crops in which resistance to herbicides or certain classes of herbicides has been induced through genetic engineering include glyphosate- and glufosinate-resistant maize varieties marketed under trade names RoundupReady®, Herculex I®, and LibertyLink®.

[0113] The term "useful plants" should be understood to include useful plants that have been transformed using recombinant DNA technology to enable the synthesis of one or more selectively acting toxins, such as those known to be derived from toxin-producing bacteria, particularly those of the genus Bacillus.

[0114] Examples of such plants include: YieldGard® (maize variety expressing CryIA(b) toxin); YieldGard Root-Eating Nematode® (maize variety expressing CryIIIB(b1) toxin); YieldGard Plus® (maize variety expressing CryIA(b) and CryIIIB(b1) toxins); Starlink® (maize variety expressing Cry9(c) toxin); Herculex I® (maize variety expressing CryIF(a2) toxin and the enzyme phosphinothrysin N-acetyltransferase (PAT) to achieve resistance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety expressing CryIA(c) toxin); Bollgard I® (cotton variety expressing CryIA(c) toxin); Bollgard II (registered trademark) (cotton varieties expressing CryIA(c) and CryIIA(b) toxins); VIPCOT (registered trademark) (cotton varieties expressing VIP toxin); NewLeaf (registered trademark) (potato varieties expressing CryIIIA toxin); NatureGard (registered trademark); Agrisure (registered trademark) GT advantages (GA21 glyphosate resistance trait); Agrisure (registered trademark) CB advantages (Bt11 corn-boring insect (CB) trait); Agrisure (registered trademark) RW (corn root-boring nematode trait); and Protecta (registered trademark).

[0115] Both plant crops and their seed materials can be resistant to herbicides and simultaneously resistant to insect feeding ("stacked" transgenic events). For example, seeds can express the insecticidal Cry3 protein while simultaneously being resistant to glyphosate.

[0116] Crop plants can also be obtained by conventional methods involving crossbreeding or genetic engineering, and should be understood to include those that possess so-called output traits (e.g., improved storage stability, higher nutritional value, and improved flavor).

[0117] Compounds of formula (I) (or compositions containing the same) can be used to control unwanted plants (collectively, "weeds"). The weeds controlled include, for example, the genera Agrostis, Alopecurus, Avena, Brachiaria, Bromus, Cenchrus, Cyperus, Digitaria, Echinochloa, Eleusine, Lolium, Monochoria, Rottboellia, Sagittaria, Scirpus, Setaria, and Moroko. It can be either monocotyledonous species such as the genus Sorghum, or dicotyledonous species such as Abutilon, Amaranthus, Ambrosia, Chenopodium, Chrysanthemum, Conyza, Galium, Ipomoea, Nasturtium, Sida, Sinapis, Solanum, Stellaria, Veronica, Viola, and Xanthium.

[0118] The compound of formula (I) may be used in an unmodified form, or, preferably, in combination with additives such as a carrier, solvent, and surfactant (SAA), which are conventionally used in the art of formulations to provide a herbicide composition. The present invention therefore further provides a herbicide composition comprising at least one compound of formula (I), an agriculturally acceptable carrier, and optionally an additive. The agriculturally acceptable carrier is, for example, a carrier suitable for agricultural use. Agricultural carriers are well known in the art.

[0119] The herbicidal composition generally comprises 0.1 to 99% by weight, particularly 0.1 to 95% by weight, of the compound of formula I, and 1 to 99.9% by weight of a compounding aid, preferably containing 0 to 25% by weight of a surface-active substance.

[0120] The composition can be selected from a number of formulation types. These include emulsion concentrates (EC), suspension concentrates (SC), suspension emulsions (SE), capsule suspensions (CS), water-dispersible granules (WG), emulsifying granules (EG), water-in-oil emulsions (EO), oil-in-water emulsions (EW), micro-emulsions (ME), oil dispersions (OD), oil-mixed flowables (OF), oil-mixed liquids (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), industrial concentrates (TK), dispersible concentrates (DC), soluble powders (SP), wettable powders (WP), and soluble granules (SG). In any case, the formulation type selected will depend on the specific intended purpose and the physical, chemical, and biological properties of the compound of formula (I).

[0121] Soluble powder (SP) can be prepared by mixing the compound of formula (I) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate, or magnesium sulfate) or one or more water-soluble organic solids (such as polysaccharides), and optionally one or more wetting agents, one or more dispersing agents, or a mixture of the said agents to improve its dispersibility / solubility in water. The mixture is then ground into a fine powder. A similar composition can also be granulated to form water-soluble granules (SG).

[0122] A wettable powder (WP) can be prepared by mixing a compound of formula (I) with one or more solid diluents or carriers, one or more wetting agents, preferably one or more dispersants, and optionally one or more suspending agents to promote dispersibility in a liquid. The mixture is then ground into a fine powder. A similar composition may be granulated to form water-dispersible granules (WG).

[0123] Granules (GR) may be formed by granulating a mixture of the compound of formula (I) and one or more powdered solid diluents or carriers, or by absorbing the compound of formula (I) (or its solution in a suitable agent) into a porous granular material (such as pumice, attapulgite clay, fuller earth, kieslager, diatomaceous earth, or crushed corn cob), or by absorbing the compound of formula (I) (or its solution in a suitable agent) into a hard core material (such as sand, silicic acid, carbonate minerals, sulfates, or phosphates), and drying as necessary, to form pre-formed compressed powder granules. Agents commonly used to aid absorption or adsorption include solvents (aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones, and esters) and binders (such as polyvinyl acetate, polyvinyl alcohol, dextrin, carbohydrates, and vegetable oils). One or more other additives may also be included in the granules (e.g., emulsifiers, wetting agents, or dispersants).

[0124] Dispersible concentrates (DCs) can be prepared by dissolving the compound of formula (I) in water or an organic solvent such as a ketone, alcohol, or glycol ether. These solutions may contain surfactants (for example, to improve dilution with water or to prevent crystallization in a spray tank).

[0125] Emulsifying concentrates (ECs) or oil-in-water emulsions (EWs) can be prepared by dissolving a compound of formula (I) in an organic solvent (optionally having one or more wetting agents, one or more emulsifiers, or a mixture of the said agents). Suitable organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes as exemplified by SOLVESSO 100, SOLVESSO 150, and SOLVESSO 200 (SOLVESSO is a registered trademark)), ketones (such as cyclohexanone or methylcyclohexanone), alcohols (such as benzyl alcohol, furfuryl alcohol, or butanol), N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone), and dimethylamides of fatty acids (C8-C 10Examples include fatty acid dimethylamides, and chlorinated hydrocarbons. When added to water, the EC product can spontaneously emulsify to provide an emulsion with sufficient stability to be suitable for spraying applications with appropriate equipment.

[0126] In the preparation of EW, the compound of formula (I) is obtained as a liquid (which may be melted at a suitable temperature, typically below 70 °C if not liquid at room temperature) or in solution (by dissolving in a suitable solvent), and then the resulting liquid or solution is emulsified under high shear into water containing one or more SAAs to provide an emulsion. Suitable solvents for use in EW include vegetable oils, chlorinated hydrocarbons (such as chlorobenzene), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes), and other suitable organic solvents with low solubility in water.

[0127] Microemulsions (ME) can be prepared by mixing a blend of one or more solvents and one or more SAAs with water to spontaneously provide a thermodynamically stable isotropic liquid formulation. The compound of formula (I) is initially present in either water or the solvent / SAA blend. Suitable solvents for use in ME include those described above for use in EC or EW. ME can be either a water-in-oil or an oil-in-water type system (which can be determined by measuring the conductivity), and is suitable for mixing water-soluble and oil-soluble pesticidal agents in the same formulation. ME can remain as a microemulsion or form a conventional oil-in-water emulsion and be suitably diluted in water.

[0128] A suspension concentrate (SC) may contain an aqueous or non-aqueous suspension of fine insoluble solid particles of a compound of formula (I). The SC can be prepared by subjecting the solid compound of formula (I) in a suitable medium, optionally together with one or more dispersants, to a ball mill or bead mill to provide a fine particle suspension of the compound. One or more wetting agents may be included in the composition and a suspending agent may be included to reduce the sedimentation rate of the particles. Alternatively, the compound of formula (I) may be subjected to a dry mill and added to water containing the agents described above in the specification to provide the desired final product.

[0129] An aerosol formulation contains a compound of formula (I) and a suitable propellant (e.g., n-butane). The compound of formula (I) may also be dissolved or dispersed in a suitable medium (e.g., water, or a hydratable liquid such as n-propanol) to provide a composition for use in a non-pressurized manual spray pump.

[0130] A capsule suspension (CS) can be prepared in the same manner as the preparation of an EW formulation, but with an additional polymerization stage such that each of the oil droplets is encapsulated within a polymeric shell and an aqueous dispersion of oil droplets containing the compound of formula (I) and optionally a carrier or diluent therefor is obtained. The polymeric shell can be produced by either an interfacial polycondensation reaction or a coacervation technique. The composition can provide a sustained release of the compound of formula (I) and can be used for seed treatment. The compound of formula (I) may also be formulated in a biodegradable polymer matrix such that the compound has a slow sustained release.

[0131] The composition may contain one or more additives to improve the biological properties of the composition, for example, by improving the wettability, retention, or distribution of the compound of formula (I) on a surface; resistance to rain on the treated surface; or uptake or mobility. Examples of such additives include surfactants (SAAs), oil-based spray additives such as certain mineral oils or natural vegetable oils (such as soybean oil and rapeseed oil), modified vegetable oils such as methylated rapeseed oil (MRSO), and blends of these with other bio-enhancing adjuvants (formulation components that can assist or modify the action of the compound of formula (I)).

[0132] The wetting agent, dispersant, and emulsifier may be cationic, anionic, amphoteric, or nonionic SAA.

[0133] Suitable cationic SAAs include quaternary ammonium compounds (e.g., cetyltrimethylammonium bromide), imidazolines, and amine salts.

[0134] Suitable anionic SAAs include alkali metal salts of fatty acids, sulfates of aliphatic monoesters (e.g., sodium lauryl sulfate), salts of sulfonated aromatic compounds (e.g., sodium dodecylbenzenesulfonate, calcium dodecylbenzenesulfonate, butylnaphthalene sulfonate, and mixtures of sodium di-isopropyl-naphthalenesulfonate and sodium tri-isopropyl-naphthalenesulfonate), ether sulfates, alcohol ether sulfates (e.g., sodium laureth-3 sulfate), ether carboxylates (e.g., sodium laureth-3 carbonate), phosphate esters (e.g., products from the reaction of one or more aliphatic alcohols with phosphoric acid (mainly monoesters) or phosphorus pentoxide (mainly diesters), such as the reaction of lauryl alcohol with tetraphosphate; these products may also be ethoxylated), sulfosuccinamates, paraffins or olefin sulfonates, taurates, lignosulfonates, and phosphates / sulfates of tristyrylphenol.

[0135] Suitable amphoteric SAAs include betaine, propionate, and glycinate.

[0136] Suitable nonionic SAAs include condensates of alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof, with aliphatic alcohols (such as oleyl alcohol or cetyl alcohol) or alkylphenols (such as octylphenol, nonylphenol, or octyl cresol); partial esters derived from long-chain fatty acids or hexitol anhydride; condensates of the partial esters with ethylene oxide; block polymers (including ethylene oxide and propylene oxide); alkanolamides; simple esters (e.g., fatty acid polyethylene glycol esters); amine oxides (e.g., lauryldimethylamine oxide); lecithin and its sorbitan and esters, alkyl polyglycosides, and tristyrylphenol.

[0137] Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone, or sodium carboxymethylcellulose) and swollen clays (such as bentonite or attapulgite).

[0138] The compounds of the present invention can also be used in mixtures with one or more additional herbicides and / or plant growth regulators. Examples of such additional herbicides or plant growth regulators include acetochlor, acifoulphene (including acifoulphene-sodium), acroniphene, ametrine, aminocarbazone, aminopyralide, aminotriazole, atrazine, beflubutamide-M, benkytrione, bensulfuron (including bensulfuron-methyl), bentazon, bicyclopyrone, viranaphos, bipirazon, bispiribac-sodium, bixurozone, bromacil, bromoxynil, butachlor, butaphenacil, and carphen. Trazone (containing carfentrazone-ethyl), chloranslam (containing chloranslam-methyl), chlorimuron (containing chlorimuron-ethyl), chlorotoluron, chlorsulfuron, scinmethiline, crasiphos, cretodym, clodinahop (containing clodinahop-propargyl), chromazon, clopyralide, cyclopyranil, cyclopyrimolate, cyclosulfamuron, cyhalofop (containing cyhalofop-butyl), 2,4-D (containing choline salt and its 2-ethylhexyl ester), 2,4-DB, Sumedifam, Dicanba (containing its aluminum, aminopropyl, bis-aminopropylmethyl, choline, dichloroprop, diglycolamine, dimethylamine, dimethylammonium, potassium and sodium salts), Diclothram, Difluhenican, Diflufenzopyr, Dimethachlor, Dimethenamide-P, Dioxopyritrone, Dicoat dibromide, Diuron, Epirifenacil, Etalfluralin, Etofmesate, Phenoxaprop (containing Phenoxaprop-P-ethyl), Phenoxasulfone Fenpyrazone, fenquinotrione, fentrazamide, flazasulfuron, floralam, florpyrauxifen (containing florpyrauxifen-benzyl), fluazihop (containing fluazihop-p-butyl), flucarbazone (containing flucarbazone-sodium), fluphenacet, flumetulam, flumioxazine, fluomethron, fomesaphenflupyrsulfuron (containing flupyrsulfuron-methyl-sodium), fluroxypil (containing fluroxypil-meptyl), fomesaphen,Folamsulfuron, glufosinate (including both L-glufosinate and ammonium salts), glyphosate (including its diammonium, isopropylammonium and potassium salts), halaxifen (including halaxifen-methyl), haloxyhop (including haloxyhop-methyl), hexazinone, hydantosidine, imazamox (including R-imazamox), imazapick, imazapyr, imazetapir, indadiflame, iodosulfuron (including iodosulfuron-methyl-sodium), iophenesulfuron (iophenesulf (Containing chlorofluorophosphate (sodium), ioxynil, isoproturone, isoxaflutol, lancotrione, MCPA, MCPB, mecoprop-P, mesosulfuron (containing mesosulfuron-methyl), mesotrione, metamitron, metazachlor, methiozoline, metrachlor, metoslam, metrivudine, metosulfuron, napropamide, nicosulfuron, norfurazone, oxadiazone, oxasulfuron, oxyfluorphen, paraquat dichloride, pendimethalin, penoxuslam, fenmedifam, picloram, pinoxadene, p Retilachlor, Primisulfuron-methyl, Promethrin, Propanyl, Propacizafop, Propyrisulfuron, Propyzamide, Prosulfocarb, Prosulfuron, Pyraclonil, Pyaflufen (including Pyaflufen-ethyl), Pyrasulfol, Pyridate, Pyriphthalide, Pyrimisulfan, Pyroxasulfone, Pyroxyslam, Quinclorac, Kimmelac, Quizalofop (including Quizalofop-P-ethyl and Quizalofop-P-tefuryl), Limisoxafen, Limusulfuron, Saflufenacil, Cethoxydim, Simazine, S- Metallochlor, sulfenthrazone, sulfosulfuron, tebutiuron, tefuryltrione, tenbotrione, terbutyrazine, terbutrin, tetoflupyrrolimeth, thiencarbazone, thifensulfuron, thiafenacil, torpylate, topramezone, tralcoxidime, triafamone, trialate, triasulfuron, tribenulon (containing tribenulon-methyl), triclopyr, trifloxysulfuron (containing trifloxysulfuron-sodium), trifludimoxazine, trifluralin, triflusulfuron, tripyrasulfone,3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidine-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylate ethyl ester, 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidinedion-2-one, 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidinedion-2-one, 5-ethoxy- 4-Hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidined-2-one, 4-Hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidined-2-one, 4-Hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazole-3-yl]imidazolidined-2-one, (4R)1-(5-tert-butyridinebutylisoxazole-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidined-2- On, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylic acid (its phytochemically acceptable esters, e.g., methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate, prop-2-inyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate and cyanomethyl 4-amino-3-chloro Ro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate), 3-ethylsulfanyl-N-(1,3,4-oxadiazole-2-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide, 3-(isopropylsulfanylmethyl)-N-(5-methyl-1,3,4-oxadiazole-2-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide,3-(isopropylsulfonylmethyl)-N-(5-methyl-1,3,4-oxadiazole-2-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide, 3-(ethylsulfonylmethyl)-N-(5-methyl-1,3,4-oxadiazole-2-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide, ethyl-2-[[3-[[3-chloro-5-fluoro-6-[3-methyl-2,6-dioxo-4-(trifluoromethyl )Pyrimidine-1-yl]-2-pyridyl]oxy]acetate, 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methylpyridazine-3-one, tetrahydrofuran-2-ylmethyl(2R)-2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridyl)oxy]propanoate, (2R)-2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridyl)oxy]propanoic acid, tetrahydrofuran-2-ylmethyl2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridyl) [Oxy]propanoate, 2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridyl)oxy]propanoic acid, 2-fluoro-N-(5-methyl-1,3,4-oxadiazole-2-yl)-3-[(R)-propylsulfinyl]-4-(trifluoromethyl)benzamide, 2-fluoro-N-(5-methyl-1,3,4-oxadiazole-2-yl)-3-propylsulfinyl-4-(trifluoromethyl)benzamide, (2-fluorophenyl)methyl6-amino-5-chloro-2-(4-chloro-2-fluoro-3- Examples include methoxyphenyl)pyrimidine-4-carboxylate, 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylic acid, 3-(3-chlorophenyl)-6-(5-hydroxy-1,3-dimethylpyrazole-4-carbonyl)-1,5-dimethylquinazoline-2,4-dione, and [4-[3-(3-chlorophenyl)-1,5-dimethyl-2,4-dioxoquinazoline-6-carbonyl]-2,5-dimethylpyrazole-3-yl]N,N-diethylcarbamate.

[0139] The compound of formula (I) may also be in the form of an ester or salt, as described, for example, in The Pesticide Manual, Sixteenth Edition, British Crop Protection Council, 2012.

[0140] The mixture can be advantageously used in the above formulations (in this case, "active ingredient" refers to the respective mixtures of the compound of formula (I) and the other compound).

[0141] The compounds or mixtures of the present invention can also be used in combination with one or more herbicide toxicity mitigators. Examples of such toxicity mitigators include benoxacol, croquintocet (including croquintocetmexil), cyprosulfamide, dichlormid, fenchlorazole (including fenchlorazole-ethyl), fenchlorim, fluxofenim, flirazole, isoxadifen (including isoxadifen-ethyl), mefenpyr (including mefenpyr-diethyl), metcamifen, and oxavethrinil.

[0142] A mixture of the compound of formula I and cyprosulfamide, isoxadifen-ethyl, croquintosetmexyl and / or metcamifene is particularly preferred.

[0143] Toxicity mitigants for compounds of formula (I) are also found, for example, in The Pesticide Manual, 16. th As described in Edition (BCPC), 2012, it may be in the form of an ester or a salt. The references to croquintosetmexil also apply to its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium, or phosphonium salts, as disclosed in International Publication No. 02 / 34048.

[0144] Preferably, the mixing ratio of the compound toxicity mitigator of formula (I) is 100:1 to 1:10, and particularly 20:1 to 1:1.

[0145] The compound of formula (I) is typically used in the form of a pesticide composition and can be applied simultaneously with or sequentially to the crop area or plant to be treated, along with further compounds. These further compounds can be, for example, fertilizers or trace element donors, or other preparations that affect plant growth. They can also be selective or non-selective herbicides, as well as insecticides, fungicides, fungicides, nematicides, mollusk repellents, or mixtures of these preparations, and may be accompanied, if desired, by further carriers, surfactants, or application enhancers that are conventionally used in the art of the formulation.

[0146] As used herein, the term “habitat” means a field where plants are growing, or where the seeds of cultivated plants are sown, or where the seeds will be sown in the soil. This includes the soil, seeds and seedlings, and established vegetation.

[0147] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.

[0148] The term “plant propagation material” is understood to refer to the reproductive parts of a plant, such as seeds, and vegetative bodies, such as cuttings or tubers, like those of potatoes, that can be used for propagation. Examples include seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, and parts of the plant. Also included are germinated plants and sprouts that will be transplanted after germination or after emerging from the soil. These sprouts may be protected by complete or partial treatment by immersion before transplanting. Preferably, “plant propagation material” is understood to refer to seeds.

[0149] The pesticidal agents referred to in this specification using common names are known, for example, from “The Pesticide Manual”, 15th Ed., British Crop Protection Council 2009.

[0150] The compounds of formula (I) can be used in the unmodified form or, preferably, in combination with adjuvants conventionally employed in the art of formulations. For this purpose, they can be conveniently formulated in known manner as emulsifiable concentrates, coating pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granules and, for example, capsules in polymeric substances. As well as the type of composition, application methods such as spraying, atomizing, dusting, scattering, coating or pouring are selected according to the intended purpose and the circumstances at the time. The compositions can also contain further adjuvants such as stabilizers, defoamers, viscosity regulators, binders or adhesives and fertilizers, sources of trace elements or other formulations for obtaining special effects.

[0151] Suitable carriers and adjuvants for use in agriculture can be solid or liquid and are substances useful in the art of formulation, for example natural or regenerated mineral substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders or fertilizers. Such carriers are described, for example, in WO 97 / 33890.

[0152] The compounds of formula (I) are usually used in the form of compositions and can be applied simultaneously or sequentially with further compounds to the crop area or plants to be treated. These further compounds can be, for example, fertilizers or trace element donors or other preparations which influence the growth of plants. They can also be selective or non-selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations and, if desired, are accompanied by further carriers, surfactants or application promoting adjuvants conventionally used in the art of formulation.

[0153] The compound of formula (I) may be the sole active ingredient in a composition, or, where appropriate, may be mixed with one or more additional active ingredients such as pesticides, fungicides, synergists, herbicides, or plant growth regulators. These additional active ingredients may, in some cases, result in unexpected synergistic activity.

[0154] Typically, a formulation comprises 0.01 to 90% by weight of an active agent, 0 to 20% of an agriculturally acceptable surfactant, and 10 to 99.99% of solid or liquid inert formulations and auxiliaries, wherein the active agent consists of at least compounds of formula (I), together with components (B) and (C) and optionally other active agents, particularly bactericides or preservatives. The concentrated form of the composition generally contains about 2 to 80%, preferably about 5 to 70% by weight of the active agent. The application form of the formulation may contain, for example, 0.01 to 20% by weight, preferably 0.01 to 5% by weight of the active agent. While commercially available products may preferably be formulated as concentrates, end users typically utilize diluted formulations.

[0155] The following table shows the individual compounds of formula (I) according to the present invention. [ka] Let's look at an example.

[0156] [Table 1-1] [Table 1-2] [Table 1-3]

[0157] Table A-1 provides 99 compounds of formula (I), A-1.001 to A-1.099, where X is O and R 1 is methyl, and R 2 It is 3,4-dichlorophenyl, and R 3 is hydrogen, and also, R4 and R 5 This is defined in Table 1.

[0158] Table A-2 provides 99 compounds of formula (I), A-2.001 to A-2.099, where X is O and R 1 is ethyl, and R 2 It is 3,4-dichlorophenyl, and R 3 is hydrogen, and also, R 4 and R 5 This is defined in Table 1.

[0159] Table A-3 provides 99 compounds of formula (I), A-3.001 to A-3.099, where X is NH and R 1 is methyl, and R 2 It is 3,4-dichlorophenyl, and R 3 is -N(CH3)2, and also, R 4 and R 5 This is defined in Table 1.

[0160] Table A-4 provides 99 compounds of formula (I), A-4.001 to A.4.099, where X is NH and R 1 is ethyl, and R 2 It is 3,4-dichlorophenyl, and R 3 is -N(CH3)2, and also, R 4 and R 5 This is defined in Table 1.

[0161] Table A-5 provides 99 compounds of formula (I), A-5.001 to A.5.099, where X is O and R 1 is ethyl, and R 2 It is 3,4-dichlorophenyl, and R 3 is methyl, and also R 4 and R 5 This is defined in Table 1.

[0162] Table A-6 provides 99 compounds of formula (I), A-6.001 to A-6.099, where X is NH and R 1 is ethyl, and R 2 It is 3,4-dichlorophenyl, and R 3 is methyl, and also R 4 and R 5 This is defined in Table 1.

[0163] Combination example

[0164] [Table 2]

[0165] A wettable powder can be obtained by thoroughly mixing the active ingredient with an auxiliary agent, thoroughly grinding this mixture in a suitable mill, and diluting it with water to obtain a suspension of the desired concentration.

[0166] [Table 3]

[0167] The active ingredient is thoroughly mixed with an auxiliary agent, and this mixture is thoroughly ground in a suitable mill to obtain a powder that can be used directly for seed treatment.

[0168] emulsifiable concentrate Active ingredient [compound of formula (I)] 10% Octylphenol polyethylene glycol ether 3% (4-5 mol of ethylene oxide) Calcium dodecylbenzenesulfonate 3% Castor oil polyglycol ether (35 mol ethylene oxide) 4% Cyclohexanone 30% Xylene mixture 50%

[0169] Any emulsion of the required dilution ratio that can be used for plant protection can be obtained from this concentrate by dilution with water.

[0170] [Table 4]

[0171] Ready-to-use powders are obtained by mixing the active ingredient with a carrier and grinding this mixture in a suitable mill. Such powders can also be used for drying and coating seeds.

[0172] Extruded granules Active ingredient [compound of formula (I)] 15% Sodium lignosulfonate 2% Carboxymethylcellulose 1% Kaolin 82%

[0173] The active ingredients are mixed and ground together with an auxiliary agent, and this mixture is moistened with water. The mixture is then extruded and dried in an airflow.

[0174] Coated granules Active ingredient [compound of formula (I)] 8% Polyethylene glycol (mol. wt. 200) 3% Kaolin 89%

[0175] Finely ground active ingredients are uniformly applied to kaolin moistened with polyethylene glycol in a mixer. This yields coated granules that do not generate dust.

[0176] Suspension concentrate Active ingredient [compound of formula (I)] 40% Propylene glycol 10% Nonylphenol polyethylene glycol ether (15 mol ethylene oxide) 6% Sodium lignosulfonate 10% Carboxymethylcellulose 1% Silicone oil (in the form of a 75% emulsion in water) 1% water 32%

[0177] Finely ground active ingredients can be completely mixed with auxiliary agents to obtain a suspension concentrate, from which a suspension with any desired dilution ratio can be obtained by dilution with water. Such dilutions allow living plants and plant propagation materials to be treated by spraying, pouring, or immersion to protect them from microbial ectoplasty.

[0178] Concentrated flowable formulation for seed treatment Active ingredient [compound of formula (I)] 40% Propylene glycol 5% Copolymer Butanol PO / EO 2% Tristyrenephenol + 10-20 moles of EO (2%) 1,2-Benzisothiazolin-3-one (in the form of a 20% aqueous solution) 0.5% Monoazo pigment calcium salt 5% Silicone oil (in the form of a 75% emulsion in water) 0.2% Water 45.3%

[0179] Finely ground active ingredients can be completely mixed with auxiliary agents to obtain a suspension concentrate, from which suspensions of any desired dilution ratio can be obtained by dilution with water. Using such dilutions, living plants and plant propagation materials can be treated by spraying, pouring, or immersion to protect them from microbial ectoparasitism.

[0180] Slow-release capsule suspension Mix 28 parts of the compound of formula (I) with 2 parts of an aromatic solvent and 7 parts of a toluene diisocyanate / polymethylene-polyphenyl isocyanate mixture (8:1). Emulsify this mixture in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of a defoamer, and 51.6 parts of water until the desired particle size is achieved. Add a mixture of 2.8 parts of 1,6-diaminohexane in 5.3 parts of water to this emulsion. Stir the mixture until the polymerization reaction is complete. Stabilize the resulting capsule suspension by adding 0.25 parts of a thickener and 3 parts of a dispersant. This capsule suspension formulation contains 28% of the active ingredient. The medium capsule size is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for this purpose. Another aspect of the present invention may be as follows: [1] Compound of formula (I): [ka] (In the formula, X is O, NR 6 or S; R 1 is C 1 ~C 6 It is alkyl; R 2 is phenyl or heteroaryl, the heteroaryl portion is a 5-membered or 6-membered aromatic ring containing 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, and each phenyl and heteroaryl portion is R 7 It may be arbitrarily substituted with one, two, three, or four bases, which may be identical or different, represented by; R 3 is hydrogen, C 1 ~C 6 Alkyl, N,N-di(C 1 ~C 3 Alkyl)amino, C 1 ~C 6 Haloalkyl, C 3 ~C 6 Cycloalkyl, C 3 ~C 6 Cycloalkyl C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy C 1 ~C 6 Alkyl, C 2 ~C 6 Alkenil, C 2~C 6 Alkinyl, phenyl, or phenyl C 1 ~C 3 It is an alkyl group, and the phenyl portion is R 8 It may be arbitrarily substituted with one, two, three, or four bases, which may be identical or different, represented by; R 4 C 3 ~C 6 Cycloalkenyl, phenyl, phenyl C 1 ~C 2 Alkyl, Phenylen C 1 ~C 2 Alkenyl, heterocyclyl (where the heterocyclyl portion is a 4-membered, 5-membered, or 6-membered non-aromatic monocyclic ring containing 1, 2, or 3 heteroatoms individually selected from N, O, and S), or heteroaryl (where the heteroaryl portion is a 5-membered or 6-membered aromatic monocyclic ring containing 1, 2, or 3 heteroatoms individually selected from N, O, and S), where the phenyl, heterocyclyl, and heteroaryl portions are each R 9 It may be arbitrarily substituted with one, two, three, or four bases, which may be identical or different, represented by; or R 4 This is a 6- to 10-membered cyclic ring system that optionally contains 1, 2, or 3 heteroatoms individually selected from N, O, and S, and the cyclic ring system is R 12 It may be optionally substituted with one or two groups represented by and the cyclized ring system is C 1 ~C 2 The remainder of the molecule is optionally bonded via an alkylene linker; R 5 is halogen, C 1 ~C 4 Alkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Haloalkoxy or C 1 ~C 4 Alkoxy C 1 ~C 4 It is alkyl; R 6 is hydrogen, C 1 ~C 3 Alkyl or C 1 ~C 6 It is an alkoxy; R 7 These are cyano, nitro, halogen, and C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Haloalkyl, C 1 ~C 6 Haloalkoxy, C 1 ~C 6 Alkoxy C 1 ~C 6 Alkyl, C 1 ~C 6 Alkyl sulfanyl, C 1 ~C 6 Alkyl sulfinyl, C 1 ~C 6 Alkyl sulfonyl, C 1 ~C 6 Alkyl sulfonamide, C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, C 1 ~C 6 It is an alkylaminocarbonyl or phenyl, and each phenyl portion is R 10 It may be arbitrarily substituted with one, two, or three bases, which may be identical or different, represented by; R 8 These are halogen, cyano, and C 1 ~C 3 Alkyl or C 1 ~C 3 It is an alkoxy; R 9 These are cyano, nitro, halogen, oxo, and C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Haloalkyl, C 1 ~C 6 Haloalkoxy, C 1 ~C 6 Alkoxy C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy C 1 ~C 6 Alkoxy, C 2 ~C 6 Alkenil, C 2 ~C 6 Alkinyl, C 2 ~C 6 Alkenyloxy, C 2 ~C 6 Alkynyloxy, C 1 ~C 6 Alkyl sulfanyl, C 1 ~C 6 Alkyl sulfinyl, C 1 ~C 6 Alkyl sulfonyl, C 1 ~C 6 Alkyl sulfonamide, C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, C 1 ~C 6 Alkylaminocarbonyl, C 3 ~C 6 Cycloalkyl, C 3 ~C 6 Cycloalkyl C 1 ~C 6 Alkoxy, N,N-di(C) 1 ~C 4 Alkyl)aminosulfonyl, C 3 ~C 6 Cycloalkylaminocarbonyl, N,N-di(C 1 ~C 4 The alkyl)aminocarbonyl, phenoxy, or benzyloxy moiety is R 12 It may be arbitrarily substituted with one or two bases, which may be identical or different, represented by; or Any two adjacent R 9 The groups, together with the carbon atoms to which they are bonded, can form a five-membered or six-membered heterocyclyl ring containing one or two heteroatoms selected from O and N, wherein the heterocyclyl ring is R 11 It may be arbitrarily substituted with one, two, three, or four bases, which may be identical or different, represented by; R 10 is halogen, C 1 ~C 3 Alkyl or C 1 ~C 3 It is an alkoxy; R 11 is halogen, C 1 ~C 3 Alkyl or C 1 ~C 3 It is an alkoxy; R 12 These are cyano, halogen, and C 1 ~C 3 Alkyl or C 1 ~C 3 (It is an alkoxy) Or, its salt or N-oxide. 〔2〕R 1 is C 1 ~C 4 The compound described in [1] above, which is alkyl. 〔3〕R 2 R is phenyl or pyridyl, and each phenyl and pyridyl portion is R 7 The compound according to [1] or [2], which may be optionally substituted with one or two groups that are identical or different and represented by . 〔4〕R 3 is hydrogen, C 1 ~C 4 Alkyl or N,N-di(C 1 ~C 3 A compound according to any one of the above items [1] to [3], which is an alkyl)amino compound. 〔5〕R 4 C 4 ~C 6 Cycloalkenyl, phenyl, phenyl C 1 ~C 2 Alkenyl, heterocyclyl (where the heterocyclyl portion is a 5-membered or 6-membered non-aromatic monocyclic ring containing one or two heteroatoms individually selected from N, O, and S), or heteroaryl (where the heteroaryl portion is a 5-membered or 6-membered aromatic monocyclic ring containing one or two heteroatoms individually selected from N, O, and S), where the phenyl, heterocyclyl, and heteroaryl portions are each R 9 The compound according to any one of the above [1] to [4], which may be optionally substituted with one, two, or three groups that are identical or different as represented by . 〔6〕R 4 is a cyclopentenyl, phenyl, styryl, heterocyclyl (where the heterocyclyl portion is a 6-membered non-aromatic monocyclic ring containing one nitrogen atom), or heteroaryl (where the heteroaryl portion is a 5-membered or 6-membered aromatic monocyclic ring containing one or two heteroatoms individually selected from N, O, and S), where the phenyl, heterocyclyl, and heteroaryl portions are each R 9 The compound according to any one of the above [1] to [5], which may be optionally substituted with one or two groups that are identical or different and represented by . 〔7〕R 4 is a phenyl or heteroaryl (where the heteroaryl portion is a 5-membered or 6-membered aromatic monocyclic ring containing one or two heteroatoms individually selected from N, O, and S), where the phenyl, heterocyclyl, and heteroaryl portions are each R 9 The compound according to any one of the above [1] to [6], which may be optionally substituted with one or two groups that are identical or different and represented by . 〔8〕R 5 C 1 ~C 3 Alkyl or C 1 ~C 2 Alkoxy C 1 ~C 2 A compound that is alkyl, as described in any one of the above items [1] to [7]. 〔9〕R 9 These are cyano, nitro, halogen, oxo, and C 1 ~C 4 Alkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkoxy C 1 ~C 4 Alkyl, C 1 ~C 4 Alkoxy C 1 ~C 4 Alkoxy, C 1 ~C 4 Alkyl sulfanyl, C 1 ~C 4 Alkyl sulfonyl, C 1 ~C 4 Alkyl sulfonamide, C 1 ~C 4 Alkylcarbonyl, C 1 ~C 4 Alkoxycarbonyl, C 3 ~C 4 Cycloalkyl, C 3 ~C 4 Cycloalkyl C 1 ~C 3 Alkoxy, N,N-di(C) 1 ~C 3 Alkyl)aminosulfonyl, C 3 ~C 4 Cycloalkylaminocarbonyl, N,N-di(C 1 ~C 3 The alkyl)aminocarbonyl, phenoxy, or benzyloxy moiety is R 12 It may be arbitrarily substituted with one or two bases, which may be identical or different, represented by; or Any two adjacent R 9 The groups, together with the carbon atoms to which they are bonded, can form a five-membered or six-membered heterocyclyl ring containing one or two heteroatoms selected from O and N, wherein the heterocyclyl ring is R 11 The compound according to any one of the above [1] to [7], which may be optionally substituted with one or two groups that are identical or different and represented by . 〔10〕R 9 These are cyano, nitro, chloro, fluoro, oxo, methyl, t-butyl, methoxy, ethoxy, isopropoxy, difluoromethyl, trifluoromethyl, trifluoromethoxy, 2,2,2-trifluoroethoxy, methoxymethyl, methoxyethoxy, methylsulfanyl, methylsulfonyl, ethylsulfonyl, acetyl, cyclopropylmethoxy, ethylcarbamoyl, cyclopropylcarbamoyl, dimethylcarbamoyl, diethylsulfamoyl, phenoxy, benzyloxy; or any two adjacent R 9 The compound according to any one of the above [1] to [9], wherein the groups, together with the carbon atoms to which they are bonded, can form a five-membered heterocyclyl ring containing two oxygen atoms, and the heterocyclyl ring may be optionally substituted with one or two fluoro groups.

[11] A herbicide composition comprising the compound described in any one of the above items [1] to

[10] and an agriculturally acceptable compounding agent.

[12] The herbicide composition according to

[11] , further comprising at least one additional pesticide.

[13] The herbicidal composition according to

[12] , wherein the additional pesticide is a herbicide or a herbicide toxicity mitigator.

[14] A method for controlling weeds in a habitat, comprising the step of applying a control amount of the composition described in any one of the above

[11] to

[13] to the habitat of the weeds.

[15] Use of a compound of formula (I) described in any one of the above items [1] to

[10] as a herbicide. [Examples]

[0181] The following non-limiting examples provide specific synthesis methods for representative compounds of the present invention referenced in Table 2 below.

[0182] Throughout this specification, temperatures are expressed in degrees Celsius (°C), and "mp." indicates the melting point. LC / MS refers to liquid chromatography-mass spectroscopy, and the apparatus and method are described below.

[0183] Method A: Waters ACQUITY UPLC-MS uses a Sample Organizer equipped with Sample Manager FTN+, H-class QSM, Column Manager, 2×Column Manager Aux, light-emitting diode array, ELSD (wavelength range (nm): 210~400), and SQD 2.

[0184] Ionization method: Electrospray. Anode and cathode: Capillary (kV) 3.0, cone (V) 35.0, source temperature (°C) 150, cone gas flow (L / Hr.) 10, desolventing gas flow (L / Hr.) 500, desolventing temperature (°C) 500. Mass range (Da): Anode 95-800, cathode 115-800. Column: Waters ACQUITY UPLC HSS T3 1.8μm 2.1×50mm

[0185] The column used the following gradient at 40°.

[0186] [Table 5]

[0187] Method B: Waters Aquity UPLC-MS using a Sample Organizer equipped with Sample Manager FTN, H-class QSM, Column Manager, 2×Column Manager Aux, LED array, ELSD, and QDA SQD 2. SQD mass spectrometer - Ionization method: electrospray (ESI), polarity: cation, capillary (kV) 3.00, cone (V) 30.00, extractor (V) 2.00, source temperature (°C) 150, desolvation temperature (°C) 350, cone gas flow (L / Hr) 0, desolvation gas flow (L / Hr) 650). Instrument equipped with a Waters HSS T3 C18 column (column length 50 mm, column inner diameter 2.3 mm, particle size 1.8 microns). Gradient elution of MeCN in 5-100% water at 0.6 ml / min over 3.3 minutes. Both MeCN and water contain 0.05% v / v TFA.

[0188] List of Abbreviations Å = angstrom, br m = broad multiplet, °C = degrees Celsius, d = doublet, DMSO = dimethyl sulfoxide, HPLC = high-performance liquid chromatography, LCMS = liquid chromatography mass spectrometry, M = molar amount, m = multiplet, MHz = megahertz, q = quadrat, s = singlet, t = triplet, THF = tetrahydrofuran, TMT = 2,4,6-trimethylmercaptotriazine.

[0189] Example 1: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-(1-methylpyrazole-4-yl)-4-oxopyridine-3-carboxylic acid (compound number 1) Step 1: Synthesis of methyl 3-(3,4-dichlorophenyl)-3-oxopropanoate [ka] Under a nitrogen atmosphere, sodium hydride (3.17 g, 79.5 mmol, 60% by mass) was added in several portions to a stirred solution of 1-(3,4-dichlorophenyl)ethanone (5.00 g, 26.5 mmol) and dimethyl carbonate (40 mL, 466 mmol), cooled to 0°C. The reaction mixture was warmed to room temperature and stirred for 16 hours. Overnight, the reaction mixture became a solid paste and stirring was impossible. As an attempt, dimethyl carbonate (10 mL) was added to form a fluid slurry for deactivation. The reaction mixture was cooled to 0°C and deactivated by adding water (25 mL) under a nitrogen atmosphere. The reaction mixture was acidified to pH 3 by adding aqueous hydrochloric acid (2 M), and then extracted with ethyl acetate. The organic extract was dried over magnesium sulfate and evaporated under reduced pressure until dry. The crude residue was purified by flash chromatography in silica gel using a gradient of ethyl acetate in 0-15% isohexane as the eluent to obtain methyl 3-(3,4-dichlorophenyl)-3-oxopropanoate (a mixture of tautomers) as a colorless liquid (5.78 g, 23.5 mmol, 89%). Enol: 1 ¹H NMR (400MHz, chloroform) δ = 12.47 (s, 1H), 7.87 (d, 1H), 7.59 (m, 3H), 7.49 (d, 1H), 5.65 (s, 1H), 3.82 (s, 3H) Keto: 1 ¹H NMR (400 MHz, chloroform): δ = 8.03 (d, 1H), 7.77 (m, 1H), 7.58 (d, 2H), 3.97 (s, 2H), 3.76 (s, 3H).

[0190] Step 2: Synthesis of methyl(Z)-3-(3,4-dichlorophenyl)-3-(ethylamino)prop-2-enoate [ka] To a stirred solution of ethylamine (2M in THF) (12.2 mL, 24.34 mmol), acetic acid (1.39 mL, 24.3 mmol) was added dropwise at 0°C. The mixture was warmed to room temperature, stirred for 1 hour, and then evaporated under reduced pressure until dry to obtain ammonium ethyl acetate (2.55 g, 24.3 mmol). Ammonium ethyl acetate (2.55 g, 24.3 mmol) was added to a solution of methyl 3-(3,4-dichlorophenyl)-3-oxopropanoate (2.00 g, 8.09 mmol) in toluene (20 mL), followed by the addition of acetic acid (0.46 mL, 8.09 mmol) and a powdered 4 Å molecular sieve. The reaction mixture was heated under reflux for 18 hours. The cooled reaction mixture was diluted with ethyl acetate, filtered, and washed with saturated sodium bicarbonate aqueous solution. The phases were separated, and the aqueous phase was extracted with ethyl acetate (×3). The combined organic extracts were washed with brine, dried over magnesium sulfate, and evaporated under reduced pressure until dry. The crude residue was purified by flash chromatography in silica gel using a gradient of ethyl acetate in 0-10% isohexane as the eluent to obtain methyl(Z)-3-(3,4-dichlorophenyl)-3-(ethylamino)prop-2-enoate as a pale yellow oil (1.54 g, 5.61 mmol, 69%). 1 ¹H NMR (400 MHz, chloroform): δ = 8.37 (br s, 1H), 7.48 (d, 1H), 7.46 (d, 1H), 7.20 (m, 1H), 4.55 (s, 1H), 3.68 (s, 3H), 3.07 (m, 2H), 1.13-1.09 (m, 3H).

[0191] Step 3: Synthesis of methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylate [ka] A stirred mixture of methyl(Z)-3-(3,4-dichlorophenyl)-3-(ethylamino)prop-2-enoate (1.50 g, 5.5 mmol) and 2,2,6-trimethyl-1,3-dioxin-4-one (0.82 g, 5.5 mmol) was heated at 120°C for 3 hours under a nitrogen atmosphere. The cooled reaction mixture was evaporated under reduced pressure until dry. The crude residue was purified by flash chromatography in silica gel using a methanol gradient in 0-10% dichloromethane as the eluent to obtain methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylate as an off-white solid (0.95 g, 2.78 mmol, 51%). 1 ¹H NMR (400 MHz, chloroform): δ = 7.56 (d, 1H), 7.50 (d, 1H), 7.24 (m, 1H), 6.41 (s, 1H), 3.72 (q, 2H), 3.55 (s, 3H), 2.42 (s, 3H), 1.13 (t, 3H).

[0192] Step 4: Synthesis of methyl 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylate [ka] To a stirred solution of methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylate (0.500 g, 1.47 mmol) in acetonitrile (5.0 mL, 95.7 mmol), N-bromosuccinimide (0.26 g, 1.47 mmol) was added in several portions at room temperature. The reaction mixture was stirred at room temperature until complete consumption of the starting material was indicated by LC-MS. The reaction mixture was deactivated by the addition of saturated sodium bicarbonate aqueous solution (30 mL), and the aqueous phase was extracted with dichloromethane (3 × 15 mL). The combined organic extract was passed through a phase separator and evaporated under reduced pressure until dry. The crude residue was purified by flash chromatography in silica gel using a gradient of ethyl acetate in 50-100% isohexane as the eluent to obtain methyl 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylate as a colorless solid (0.602 g, 1.44 mmol, 98%). 1 ¹H NMR (400 MHz, chloroform): δ = 7.57 (d, 1H), 7.49 (d, 1H), 7.23 (m, 1H), 3.85 (q, 2H), 3.57 (s, 3H), 2.74 (s, 3H), 1.17 (t, 3H).

[0193] Step 5: Synthesis of 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid [ka] A solution of methyl 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylate (2.50 g, 5.97 mmol) in methanol (15 mL) was mixed with a solution of lithium hydroxide monohydrate (1.00 g, 23.9 mmol) in water (6 mL). The resulting solution was heated at 80°C for 2 hours. The cooled reaction mixture was acidified to pH 1-2 by adding concentrated hydrochloric acid. The precipitated solid was collected by filtration, washed with cold water, and dried to obtain 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid as a white powder (1.84 g, 4.54 mmol, 76%). 1 ¹H NMR (400 MHz, methanol-d4): δ = 7.68 (d, 1H), 7.64 (d, 1H), 7.33 (m, 1H), 4.03 (q, 2H), 2.89 (s, 3H), 1.19 (t, 3H).

[0194] Step 6: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-(1-methylpyrazole-4-yl)-4-oxopyridine-3-carboxylic acid (compound number 1) [ka] A mixture of 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (0.25 g, 0.62 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole (0.32 g, 1.54 mmol), potassium carbonate (0.17 g, 1.23 mmol), and a dichloromethane complex (1:1) of dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II) (0.10 g, 0.123 mmol) in acetonitrile (1.4 mL) and water (0.27 mL) was heated at 100 °C for 0.5 hours under microwave irradiation. The cooled reaction mixture was inactivated by adding aqueous hydrochloric acid (2 M) and extracted with ethyl acetate (×2). The combined organic extracts were evaporated under reduced pressure until dry. The crude residue was purified by reverse-phase HPLC to obtain 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-(1-methylpyrazole-4-yl)-4-oxopyridine-3-carboxylic acid as an orange solid (0.073 g, 0.18 mmol, 29%). 1 ¹H NMR (400 MHz, chloroform): δ = 7.70 (s, 1H), 7.58 (d, 1H), 7.53 (s, 1H), 7.38 (d, 1H), 7.14 (m, 1H), 3.99 (s, 3H), 3.94 (q, 2H), 2.64 (s, 3H), 1.23 (t, 3H).

[0195] Example 2: Synthesis of 5-(4-chlorophenyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (compound number 10) [ka] A mixture of 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (500 mg, 1.234 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.175 g, 0.25 mmol), potassium carbonate (0.69 g, 4.94 mmol), and (4-chlorophenyl)boronic acid (0.579 g, 3.70 mmol) was mixed with a mixture of degassed acetonitrile (15 mL) and water (3 mL) at room temperature under a nitrogen atmosphere. The reaction mixture was heated at 100 °C for 0.5 hours under microwave irradiation. The cooled reaction mixture was filtered through a TMT isolute cartridge, and the solution was freeze-dried. The crude residue was extracted with dichloromethane, and the combined extract was evaporated under reduced pressure until dry. The crude residue was purified by reverse-phase HPLC to obtain 5-(4-chlorophenyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (296 mg, 0.68 mmol, 55%). 1 ¹H NMR (400 MHz, chloroform): δ = 7.61 (d, 1H), 7.49 (d, 2H), 7.41 (d, 1H), 7.21-7.16 (m, 3H), 3.94 (q, 2H), 2.42 (s, 3H), 1.25 (t, 3H).

[0196] Example 3: Synthesis of 5-(4-chlorophenyl)-2-(3,4-dichlorophenyl)-1-ethyl-N',N',6-trimethyl-4-oxopyridine-3-carbohydrazide (compound number 2) [ka] To a stirred solution of 5-(4-chlorophenyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (0.060 g, 0.14 mmol) in dichloromethane (1.2 mL), 1,1-dimethylhydrazine (0.025 g, 0.41 mmol), dimethylaminopyridine (0.017 g, 0.14 mmol), and a solution of propylphosphonic anhydride (50 wt.%, 0.13 g, 0.21 mmol in ethyl acetate) were added. The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was evaporated under reduced pressure until dry. The crude residue was purified by reverse-phase HPLC to obtain 5-(4-chlorophenyl)-2-(3,4-dichlorophenyl)-1-ethyl-N',N',6-trimethyl-4-oxopyridine-3-carbohdrazide (0.038 g, 0.08 mmol, 58%). 1 ¹H NMR (400 MHz, chloroform): δ = 7.58 (d, 1H), 7.52-7.42 (m, 3H), 7.31-7.22 (m, 1H), 7.16 (d, 2H), 3.88 (q, 2H), 2.75 (s, 6H), 2.33 (s, 3H), 1.20 (t, 3H).

[0197] Example 4: Synthesis of 2-(3,4-dichlorophenyl)-5-(2,4-difluorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (compound number 3) Step 1: Synthesis of methyl 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxopyridine-3-carboxylate [ka] To a solution of methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylate (5.60 g, 16.5 mmol) in acetonitrile (56.0 mL), 1-iodopyrrolidine-2,5-dione (3.70 g, 16.5 mmol), followed by 2,2,2-trifluoroacetic acid (0.564 g, 0.381 mL, 4.94 mmol) was added at room temperature under a nitrogen atmosphere. The reaction mixture was heated at 80 °C for 36 hours, then stirred at room temperature for 48 hours. The cooled reaction mixture was deactivated by adding saturated sodium bicarbonate aqueous solution (200 mL) and extracted with dichloromethane (×3). The combined organic extracts were washed with saturated sodium thiosulfate solution, then with brine, dried over magnesium sulfate, filtered, and evaporated under reduced pressure. The crude residue was purified by flash chromatography in silica gel using a gradient of ethyl acetate in cyclohexane from 0 to 100% as the eluent to obtain methyl 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxopyridine-3-carboxylate as a white solid (5.33 g, 11.4 mmol, 70%). 1 ¹H NMR (400 MHz, chloroform): δ = 7.57 (d, 1H), 7.49 (d, 1H), 7.23 (m, 1H), 3.89 (q, 2H), 3.57 (s, 3H), 2.88 (s, 3H), 1.17 (t, 3H).

[0198] Step 2: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxopyridine-3-carboxylic acid [ka] Similar to 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid, methyl 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxopyridine-3-carboxylate (1.00 g, 2.15 mmol) and lithium hydroxide hydrate (0.360 g, 8.58 mmol) were used and heated at 80°C for 18 hours to prepare 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxopyridine-3-carboxylic acid (0.93 g, 2.06 mmol, 96%). 1 ¹H NMR (400 MHz, chloroform): δ = 7.60 (d, 1H), 7.34 (d, 1H), 7.10 (dd, 1H), 4.02 (q, 2H), 3.00 (s, 3H), 1.23 (t, 3H).

[0199] Step 3: Synthesis of 2-(3,4-dichlorophenyl)-5-(2,4-difluorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid [ka] To a mixture of degassed 1,4-dioxane (6 mL) and water (1 mL), a mixture of 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxopyridine-3-carboxylic acid (0.400 g, 0.88 mmol), (2,4-difluorophenyl)boronic acid (0.215 g, 1.36 mmol), and chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) (XPhos Pd G2, 0.070 g, 0.089 mmol) was added under a nitrogen atmosphere at room temperature. Tripotassium phosphate monohydrate (0.560 g, 2.6 mmol) was then added. The reaction mixture was heated at 100°C for 1 hour under microwave irradiation. The cooled reaction mixture was poured into aqueous hydrochloric acid (2M) and extracted with dichloromethane. The combined organic extract was dried over magnesium sulfate and evaporated under reduced pressure until dry. The crude residue was purified by flash chromatography in silica gel using a gradient of ethyl acetate in 0-100% cyclohexane as the eluent. The isolated material was further purified by reversed-phase HPLC to obtain 2-(3,4-dichlorophenyl)-5-(2,4-difluorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid as a cream-colored solid (0.15 g, 0.34 mmol, 39%). 1 ¹H NMR (400 MHz, chloroform): δ = 7.62 (m, 1H), 7.43 (m, 1H), 7.27-7.33 (m, 1H), 7.18 (m, 1H), 6.95-7.09 (m, 2H), 3.91-4.02 (m, 2H), 2.43 (d, 3H), 1.26 (t, 3H).

[0200] Example 5: Synthesis of 5-(4-chlorophenyl)-2-(3,4-dichlorophenyl)-1,6-dimethyl-4-oxopyridine-3-carboxylic acid (compound number 5) Step 1': Synthesis of ethyl(Z)-3-(3,4-dichlorophenyl)-3-(methylamino)prop-2-enoate [ka] Ethyl(Z)-3-(3,4-dichlorophenyl)-3-(methylamino)prop-2-enoate was prepared in the same manner as methyl(Z)-3-(3,4-dichlorophenyl)-3-(ethylamino)prop-2-enoate, using ethyl3-(3,4-dichlorophenyl)-3-oxopropanoate (1.5 g, 5.7 mmol) and methylammonium acetic acid (1.6 g, 17 mmol) to obtain ethyl(Z)-3-(3,4-dichlorophenyl)-3-(methylamino)prop-2-enoate (0.702 g, 2.56 mmol, 45%). 1 ¹H NMR (400MHz, chloroform): δ = 8.39 (br m, 1H), 7.49-7.46 (m, 2H), 7.20 (m, 1H), 6.86 (m, 1H), 4.57 (s, 1H), 4.14 (q, 2H), 2.76 (d, 3H), 1.27 (t, 3H).

[0201] Step 1: Synthesis of 5-iodo-2,2,6-trimethyl-1,3-dioxin-4-one [ka] 1-iodopyrrolidine-2,5-dione (4.0 g, 18 mmol) was added to a solution of 2,2,6-trimethyl-1,3-dioxin-4-one (2.5 g, 18 mmol) in acetic acid (45 mL) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was deactivated with water and extracted with dichloromethane (2 × 200 mL). The combined organic extracts were sequentially washed with sodium metabisulfite solution and 10% sodium bicarbonate aqueous solution, dried over magnesium sulfate, filtered, and concentrated. The crude residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate in 0-100% cyclohexane as the eluent to obtain 5-iodo-2,2,6-trimethyl-1,3-dioxin-4-one (0.900 g, 3.36 mmol, 19%) as a yellow solid. 1 ¹H NMR (400 MHz, chloroform): δ = 2.34–2.24 (m, 3H), 1.75–1.68 (m, 6H).

[0202] Step 2: Synthesis of 5-(4-chlorophenyl)-2,2,6-trimethyl-1,3-dioxin-4-one [ka] To a stirred solution of 5-iodo-2,2,6-trimethyl-1,3-dioxin-4-one (0.300 g, 1.12 mmol) in acetonitrile (6 mL) and water (4 mL), (4-chlorophenyl)boronic acid (0.525 g, 3.36 mmol) and potassium carbonate (0.625 g, 4.48 mmol) were added, and the solution was degassed under a nitrogen atmosphere for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (0.159 g, 0.224 mmol) was added to the mixture, and the reaction mixture was heated at 100°C for 0.75 hours under microwave irradiation. The cooled reaction mixture was diluted with water and extracted with ethyl acetate (×2). The combined organic extract was evaporated until dry. The crude residue was purified by flash chromatography in silica gel using a gradient of ethyl acetate in 0-15% cyclohexane as the eluent to obtain 5-(4-chlorophenyl)-2,2,6-trimethyl-1,3-dioxin-4-one (0.190 g, 0.752 mmol, 67%). 1 ¹H NMR (500 MHz, chloroform): δ = 7.40-7.34 (m, 2H), 7.24-7.18 (m, 2H), 1.97-1.91 (m, 3H), 1.79-1.74 (m, 6H).

[0203] Step 3: Synthesis of ethyl 5-(4-chlorophenyl)-2-(3,4-dichlorophenyl)-1,6-dimethyl-4-oxopyridine-3-carboxylate [ka] A stirred mixture of ethyl(Z)-3-(3,4-dichlorophenyl)-3-(methylamino)prop-2-enoate (0.206 g, 0.752 mmol) and 5-(4-chlorophenyl)-2,2,6-trimethyl-1,3-dioxin-4-one (0.190 g, 0.752 mmol) was heated at 120°C for 4 hours under a nitrogen atmosphere, and then allowed to stand at room temperature for 18 hours. After evaporation onto diatomaceous earth, the crude residue was purified by flash chromatography in silica gel using a gradient of ethyl acetate in 5-100% cyclohexane as the eluent to obtain ethyl 5-(4-chlorophenyl)-2-(3,4-dichlorophenyl)-1,6-dimethyl-4-oxopyridine-3-carboxylate (0.050 g, 0.11 mmol, 15%). 1 ¹H NMR (400MHz, chloroform): δ = 7.63-7.58 (m,1H), 7.57-7.52 (m,1H), 7.42-7.37 (m,2H), 7.27-7.26 (m,1H), 7.21-7.15 (m,2H), 4.09-4.01 (m,2H), 3.41-3.30 (m,3H), 2.30-2.24 (m,3H), 1.10-1.00 (m,3H).

[0204] Step 4: Synthesis of 5-(4-chlorophenyl)-2-(3,4-dichlorophenyl)-1,6-dimethyl-4-oxopyridine-3-carboxylic acid [ka] Similar to 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid, ethyl 5-(4-chlorophenyl)-2-(3,4-dichlorophenyl)-1,6-dimethyl-4-oxopyridine-3-carboxylate (0.050 g, 0.11 mmol) and lithium hydroxide hydrate (0.019 g, 0.44 mmol) were used and heated at 80°C for 1.5 hours to prepare 5-(4-chlorophenyl)-2-(3,4-dichlorophenyl)-1,6-dimethyl-4-oxopyridine-3-carboxylic acid (0.037 g, 0.086 mmol). 1¹H NMR (400 MHz, chloroform): δ = 7.66-7.61 (m, 1H), 7.53-7.46 (m, 2H), 7.39-7.33 (m, 1H), 7.23-7.18 (m, 2H), 7.16-7.08 (m, 1H), 3.50-3.39 (m, 3H), 2.42-2.32 (m, 3H).

[0205] Example 6: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid (compound number 6) [ka] A mixture of 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (200 mg, 0.49 mmol), potassium carbonate (0.27 g, 1.975 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.070 g, 0.099 mmol), and (2-fluoro-3-pyridyl)boronic acid (0.209 g, 1.48 mmol) was mixed with a mixture of degassed acetonitrile (6 mL) and water (1.2 mL) at room temperature under a nitrogen atmosphere. The reaction mixture was heated at 100°C for 0.5 hours under microwave irradiation. The cooled reaction mixture was diluted with water and then evaporated in a freeze-dryer until dry. The crude residue was extracted with dichloromethane, the solution was filtered, and evaporated under reduced pressure until dry. The crude residue was purified by reverse-phase HPLC to obtain 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid as a white solid (0.022 g, 0.054 mmol, 11%). 1 ¹H NMR (400 MHz, chloroform): δ = 8.36-8.35 (m, 1H), 7.85 (m, 1H), 7.63 (m, 1H), 7.45-7.37 (m, 2H), 7.18 (m, 1H), 4.01-3.95 (m, 2H), 2.45 (d, 3H), 3.10 (t, 3H).

[0206] Example 7: Synthesis of 5-(4-chlorophenyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-(methoxymethyl)-4-oxopyridine-3-carboxylic acid (compound number 7) Step 1: Synthesis of methyl 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-(iodomethyl)-4-oxopyridine-3-carboxylate [ka] To a stirred solution of methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylate (10.0 g, 29.4 mmol) in acetonitrile (100 mL), 1-iodopyrrolidine-2,5-dione (6.61 g, 29.4 mmol), followed by 2,2,2-trifluoroacetic acid (1.01 g, 8.82 mmol), was added at room temperature under a nitrogen atmosphere. The reaction mixture was heated at 80°C for 5 hours. 1-iodopyrrolidine-2,5-dione (0.500 g, 2.22 mmol) was further added, and the reaction mixture was heated at 80°C for a further 2 hours. The reaction mixture was deactivated by adding saturated sodium bicarbonate solution (100 mL) and extracted with dichloromethane (3 × 100 mL). The combined organic extracts were washed with 50 mL of 5% aqueous sodium metabisulfite solution, then with 50 mL of water, dried over magnesium sulfate, filtered, and evaporated under reduced pressure until dry. The crude residue was purified by flash chromatography in silica gel using a gradient of ethyl acetate in 5-100% cyclohexane as the eluent to obtain methyl 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-(iodomethyl)-4-oxopyridine-3-carboxylate (1.124 g, 1.90 mmol, 6%). 1 ¹H NMR (400 MHz, chloroform): δ = 7.61-7.55 (m, 1H), 7.54-7.45 (m, 1H), 7.26-7.22 (m, 1H), 4.99-4.32 (m, 2H), 4.05-3.91 (m, 2H), 3.60-3.50 (m, 3H), 1.30-1.22 (m, 3H).

[0207] Step 2: Synthesis of methyl 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-(methoxymethyl)-4-oxopyridine-3-carboxylate [ka] A solution of methyl 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-(iodomethyl)-4-oxopyridine-3-carboxylate (0.200 g, 0.338 mmol) in methanol (3 mL) was mixed with a solution of sodium methoxide in methanol (0.236 mL, 1.01 mmol) at room temperature. The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was evaporated under reduced pressure, and the residue was acidified to pH 2 by carefully adding concentrated hydrochloric acid. The precipitated solid was collected by filtration to obtain methyl 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-(methoxymethyl)-4-oxopyridine-3-carboxylate (0.1492 g, 0.3007 mmol, 89.0) as a yellow powder. 1 ¹H NMR (400MHz, chloroform): δ = 7.60-7.56 (m,1H), 7.52-7.48 (m,1H), 7.26-7.20 (m,1H), 5.04-4.98 (m,2H), 4.09-4.00 (m,2H), 3.62-3.57 (m,3H), 3.54-3.47 (m,3H), 1.18-1.11 (m,3H).

[0208] Step 3: Synthesis of methyl 5-(4-chlorophenyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-(methoxymethyl)-4-oxopyridine-3-carboxylate [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid, methyl 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-(methoxymethyl)-4-oxopyridine-3-carboxylate (0.137 g, 0.276 mmol) and (4-chlorophenyl)boronic acid (0.130 g, 0.828 mmol) were used and heated at 100°C for 1 hour to prepare methyl 5-(4-chlorophenyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-(methoxymethyl)-4-oxopyridine-3-carboxylate (0.109 g, 0.227 mmol, 82%). 1 ¹H NMR (400MHz, chloroform): δ = 7.61-7.55 (m,2H), 7.42-7.39 (m,2H), 7.33-7.29 (m,1H), 7.29-7.28 (m,1H), 7.27-7.26 (m,1H), 4.25-4.17 (m,2H), 4.01-3.90 (m,2H), 3.59-3.53 (m,3H), 3.32-3.24 (m,3H), 1.21-1.14 (m,3H).

[0209] Step 4: Synthesis of 5-(4-chlorophenyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-(methoxymethyl)-4-oxopyridine-3-carboxylic acid [ka] Similar to 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid, methyl 5-(4-chlorophenyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-(methoxymethyl)-4-oxopyridine-3-carboxylate (0.109 g, 0.227 mmol) and lithium hydroxide hydrate (0.038 g, 0.907 mmol) were used to prepare 5-(4-chlorophenyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-(methoxymethyl)-4-oxopyridine-3-carboxylic acid (0.076 g, 0.162 mmol, 71%) as an off-white powder. 1 H NMR (400MHz, methanol-d4) δ=7.77-7.70(m,2H),7.57-7.51(m,2H),7.45-7.38(m,1H),7.39- 7.31(m,2H),4.40-4.32(m,2H),4.26-4.12(m,2H),3.31-3.27(m,3H),1.32-1.21(m,3H).

[0210] Example 8: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-5-(6-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid (compound number 8) [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid, 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid was prepared using 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (0.100 g, 0.25 mmol) and (6-fluoro-3-pyridyl)boronic acid (0.104 g, 0.7406 mmol) to obtain 2-(3,4-dichlorophenyl)-1-ethyl-5-(6-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid as a white solid (0.065 g, 0.15 mmol, 63%). 1 ¹H NMR (400MHz, chloroform): δ = 8.11 (br m, 1H), 7.79 (m, 1H), 7.63-7.59 (m, 1H), 7.41 (d, 1H), 7.17 (m, 1H), 7.10 (m, 1H), 3.96 (q, 2H), 2.46 (s, 3H), 1.27 (t, 3H).

[0211] Example 9: Synthesis of 5-(4-chloro-3-fluorophenyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (compound number 9) [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid, 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (100 mg, 0.25 mmol) and (4-chloro-3-fluorophenyl)boronic acid (0.130 g, 0.75 mmol) were used to obtain 5-(4-chloro-3-fluorophenyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (0.044 g, 0.098 mmol, 39%). 1 ¹H NMR (500MHz, methanol-d4): δ = 7.70 (d,1H), 7.65 (d,1H), 7.60 (t,1H), 7.35 (m,1H), 7.26-7.18 (m,1H), 7.15-7.06 (m,1H), 4.02 (q,2H), 2.45 (s,3H), 1.22 (t,3H).

[0212] Example 10: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-5-(4-fluorophenyl)-6-methyl-4-oxopyridine-3-carboxylic acid (compound number 11) [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid, 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (0.250 g, 0.62 mmol) (4-fluorophenyl)boronic acid (0.130 g, 0.926 mmol, 100% by mass) and potassium carbonate (0.172 g, 1.23 mmol) were used to prepare 2-(3,4-dichlorophenyl)-1-ethyl-5-(4-fluorophenyl)-6-methyl-4-oxopyridine-3-carboxylic acid (0.088 g, 0.21 mmol, 34%). 1¹H NMR (400 MHz, chloroform): δ = 7.66-7.60 (m, 1H), 7.43-7.35 (m, 1H), 7.24-7.12 (m, 5H), 4.02-3.94 (m, 2H), 2.46-2.38 (m, 3H), 1.28-1.17 (m, 3H).

[0213] Example 11: Synthesis of 5-(6-chloro-3-pyridyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (compound number 12) [ka] A stirred mixture of 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxopyridine-3-carboxylic acid (0.800 g, 1.77 mmol), (6-chloro-3-pyridyl)boronic acid (0.557 g, 3.54 mmol), 1,4-dioxane (14.4 mL), and water (3.20 mL) was degassed under a nitrogen stream for 20 minutes. Then, (2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II)methanesulfonic acid (XPhos Pd G3, 0.150 g, 0.177 mmol), followed by tribasic potassium phosphate (1.13 g, 5.31 mmol), was added. The reaction mixture was heated at 100°C for 1 hour under microwave irradiation. The cooled reaction mixture was poured into aqueous hydrochloric acid (2M) and extracted with dichloromethane. The combined extract was evaporated under reduced pressure until dry. The crude residue was purified by flash chromatography in silica gel using a gradient of ethyl acetate in 0-100% cyclohexane as the eluent to obtain 5-(6-chloro-3-pyridyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid as a white solid (0.207 g, 0.47 mmol, 27%). 1¹H NMR (400MHz, chloroform): δ = 8.28 (d, 1H), 7.65 (m, 1H), 7.62 (d, 1H), 7.48 (d, 1H), 7.40 (d, 1H), 7.16 (m, 1H), 3.96 (m, 2H), 2.46 (s, 3H), 1.26 (t, 3H).

[0214] Example 12: Synthesis of 5-(2-chlorophenyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (compound number 13) [ka] A mixture of 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxopyridine-3-carboxylic acid (0.117 g, 0.25 mmol), (2-chlorophenyl)boronic acid (0.405 g, 2.59 mmol), tribasic potassium phosphate (0.165 g, 0.78 mmol), and (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II)methanesulfonic acid (S Phos G3, 0.044 g, 0.052 mmol) was mixed with a mixture of degassed 1,4-dioxane (1.8 mL) and water (0.4 mL) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with water and freeze-dried. The crude residue was purified by reverse-phase HPLC to obtain 5-(2-chlorophenyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid as a brown solid (0.039 g, 0.089 mmol, 35%). 1 ¹H NMR (400 MHz, chloroform): δ = 7.62 (m, 1H), 7.58-7.54 (m, 1H), 7.47-7.39 (m, 3H), 7.27-7.25 (m, 1H), 7.20 (m, 1H), 3.98 (q, 2H), 2.37 (s, 3H), 1.26 (t, 3H).

[0215] Example 13: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluorophenyl)-6-methyl-4-oxopyridine-3-carboxylic acid (compound number 14) [ka] Similar to 5-(6-chloro-3-pyridyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid, 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxopyridine-3-carboxylic acid (117 mg, 0.26 mmol) and 2-fluorophenylboronic acid (0.381 g, 2.59 mmol) were used to prepare 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluorophenyl)-6-methyl-4-oxopyridine-3-carboxylic acid as a white solid (0.019 g, 0.045 mmol, 17%). 1 ¹H NMR (400 MHz, chloroform): δ = 7.62 (m, 1H), 7.49-7.42 (m, 2H), 7.32-7.17 (m, 4H), 3.96 (q, 2H), 2.43 (s, 3H), 1.26 (t, 3H).

[0216] Example 14: Synthesis of 5-(2,4-dichlorophenyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (compound number 15) [ka] Similar to 5-(2-chlorophenyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid, 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxopyridine-3-carboxylic acid (0.700 g, 1.55 mmol) and (2,4-dichlorophenyl)boronic acid (0.591 g, 3.10 mmol) were used and heated at 100°C for 1 hour under microwave irradiation to prepare 5-(2,4-dichlorophenyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid as a mixture of atrop isomers (0.195 g, 0.41 mmol, 27%). 1 ¹H NMR (400 MHz, chloroform): δ = 7.64-7.56 (m, 2H), 7.45-7.38 (m, 2H), 7.22-7.15 (m, 2H), 3.96 (q, 2H), 2.37 (s, 3H), 1.25 (t, 3H).

[0217] Example 15: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-[3-(trifluoromethoxy)phenyl]pyridine-3-carboxylic acid (compound number 16) [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid, 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxopyridine-3-carboxylic acid (0.110 g, 0.2433 mmol) and 3-(trifluoromethoxy)phenylboronic acid (0.153 g, 0.73 mmol) were used to prepare 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-[3-(trifluoromethoxy)phenyl]pyridine-3-carboxylic acid (0.063 g, 0.13 mmol, 53%). 1¹H NMR (400MHz, chloroform): δ = 7.61 (d, 1H), 7.54 (t, 1H), 7.41 (d, 1H), 7.32-7.30 (m, 1H), 7.21 (d, 1H), 7.16 (dd, 1H), 7.12 (br m, 1H), 3.96 (q, 2H), 2.42 (s, 3H), 1.26 (t, 3H).

[0218] Example 16: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-5-(4-methoxyphenyl)-6-methyl-4-oxopyridine-3-carboxylic acid (compound number 18) [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid, 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxopyridine-3-carboxylic acid (0.110 g, 0.24 mmol) and 4-methoxyphenylboronic acid (0.113 g, 0.73 mmol) were used to prepare 2-(3,4-dichlorophenyl)-1-ethyl-5-(4-methoxyphenyl)-6-methyl-4-oxopyridine-3-carboxylic acid as a brown solid (0.060 g, 0.14 mmol, 57%). 1 ¹H NMR (400 MHz, chloroform): δ = 7.60 (d, 1H), 7.41 (d, 1H), 7.18-7.15 (m, 3H), 7.03 (d, 2H), 3.95 (q, 2H), 3.86 (s, 3H), 2.44 (s, 3H), 1.25 (t, 3H).

[0219] Example 17: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-(3-pyridyl)pyridine-3-carboxylic acid (compound number 19) Step 1: Synthesis of methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-(3-pyridyl)pyridine-3-carboxylate [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid, methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylate (0.100 g, 0.24 mmol) and 3-pyridylboronic acid (0.088 g, 0.72 mmol) were used to prepare methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-(3-pyridyl)pyridine-3-carboxylate as a brown gum (0.050 g, 0.119 mmol). 1 ¹H NMR (400MHz, chloroform): δ = 8.59 (m, 1H), 8.47 (d, 1H), 7.68 (m, 1H), 7.59 (d, J=8.2Hz, 1H), 7.57 (d, 1H), 7.37 (m, 1H), 7.31 (m, 1H), 3.84 (q, 2H), 3.57 (s, 3H), 2.34 (s, 3H), 1.20 (t, 3H).

[0220] Step 2: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-(3-pyridyl)pyridine-3-carboxylic acid [ka] A solution of methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-(3-pyridyl)pyridine-3-carboxylate (0.185 g, 0.443 mmol) in methanol (5 mL) and water (2.5 mL) was mixed with lithium hydroxide monohydrate (0.037 g, 0.89 mmol). The reaction mixture was heated under reflux for 5 hours. Methanol was removed under reduced pressure, and the pH was adjusted to pH 4 by adding concentrated hydrochloric acid. The precipitated solid was collected by filtration, washed with cyclohexane, and dried to obtain 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-(3-pyridyl)pyridine-3-carboxylic acid (0.106 g, 0.26 mmol, 59%). 1H NMR(500MHz,DMSO-d6):δ=8.96-8.81(m,2H),8.37-8.24(m,1H),8.05-7.96(m,1H),7.73-7.66(m,1 H),7.60-7.52(m,1H),7.36-7.27(m,1H),4.03-3.97(m,3H),2.52-2.45(m,3H),1.29-1.20(m,3H).

[0221] Example 18: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-(4-methyl-3-thienyl)-4-oxopyridine-3-carboxylic acid (compound number 20) [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid, 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylate (0.100 g, 0.24 mmol) and (4-methyl-3-thienyl)boronic acid (0.105 g, 0.74 mmol) were used to prepare 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-(4-methyl-3-thienyl)-4-oxopyridine-3-carboxylic acid as a brown oil (0.025 g, 0.059 mmol, 24%). 1 ¹H NMR (400 MHz, chloroform): δ = 7.62 (m, 1H), 7.43 (m, 1H), 7.22-7.14 (m, 3H), 3.92 (q, 2H), 2.42 (s, 3H), 2.08 (d, 3H), 1.26 (t, 3H).

[0222] Example 19: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-pyridine-1-ium-3-ylpyridine-3-carboxylic acid; 2,2,2-trifluoroacetate (compound number 21) [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid, 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylate (0.250 g, 0.617 mmol) and 3-pyridylboronic acid (0.228 g, 1.85 mmol) were used and prepared by heating at 100°C for 0.5 hours under microwave irradiation. Purification by reverse-phase HPLC in the presence of trifluoroacetic acid yielded 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-pyridin-1-ium-3-ylpyridine-3-carboxylic acid; 2,2,2-trifluoroacetate (0.044 g, 0.085 mmol, 14%). 1 ¹H NMR (400MHz, methanol-d4): δ = 8.80-8.77 (m,1H), 8.75-8.68 (m,1H), 8.29-8.23 (m,1H), 7.96-7.90 (m,1H), 7.75-7.72 (m,1H), 7.69-7.64 (m,1H), 7.41-7.29 (m,1H), 4.10-3.99 (m,2H), 2.53-2.44 (m,3H), 1.26-1.18 (m,3H).

[0223] Example 20: Synthesis of 5-(3-chloro-4-fluorophenyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (compound number 22) [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid, 5-(3-chloro-4-fluorophenyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (0.110 g, 0.243 mmol) and (3-chloro-4-fluorophenyl)boronic acid (0.127 g, 0.73 mmol) were used to prepare 5-(3-chloro-4-fluorophenyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid as a clear oil (0.065 g, 0.142 mmol, 58%). 1 ¹H NMR (400MHz, chloroform): δ = 7.60 (d, 1H), 7.40 (d, 1H), 7.32 (m, 1H), 7.29-7.15 (m, 2H), 7.17-7.12 (m, 2H), 3.94 (q, 2H), 2.42 (s, 3H), 1.24 (t, 3H).

[0224] Example 21: Synthesis of 5-(5-chloro-3-pyridyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (compound number 23) [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid, 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylate (0.100 g, 0.243 mmol) and (5-chloro-3-pyridyl)boronic acid (0.117 g, 0.74 mmol) were used to prepare 5-(5-chloro-3-pyridyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (0.023 g, 0.053 mmol, 21%). 1¹H NMR (400MHz, chloroform): δ = 8.66 (br m, 1H), 8.40 (br m, 1H), 7.22 (s, 1H), 7.62 (d, 1H), 7.41 (d, 1H), 7.17 (m, 1H), 3.96 (q, 2H), 2.45 (s, 3H), 1.26 (t, 3H).

[0225] Example 22: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-phenylpyridine-3-carboxylic acid (compound number 24) Step 1: Synthesis of methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-phenylpyridine-3-carboxylate [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-(1-methylpyrazole-4-yl)-4-oxopyridine-3-carboxylic acid, methyl 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylate (0.100 g, 0.24 mmol) and phenylboronic acid (0.087 g, 0.72 mmol) were used to prepare methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-phenylpyridine-3-carboxylate as a white solid (0.053 g, 0.13 mmol, 53%). 1 ¹H NMR (400MHz, chloroform): δ = 7.59 (d,1H), 7.57 (d,1H), 7.44-7.39 (m,2H), 7.36-7.32 (m,1H), 7.30 (m,1H), 7.25-7.21 (m,2H), 3.84 (q,2H), 3.56 (s,3H), 2.31 (s,3H), 1.19 (t,3H).

[0226] Step 2: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-phenylpyridine-3-carboxylic acid [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-(3-pyridyl)pyridine-3-carboxylic acid, 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-phenylpyridine-3-carboxylate (0.052 g, 0.12 mmol) and lithium hydroxide monohydrate (0.010 g, 0.25 mmol) were used to prepare 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-phenylpyridine-3-carboxylic acid as a white solid (0.051 g, 0.13 mmol, 100%). 1 ¹H NMR (400 MHz, chloroform): δ = 7.60 (d, 1H), 7.53-7.48 (m, 2H), 7.46-7.40 (m, 2H), 7.26-7.22 (m, 2H), 7.18 (m, 1H), 3.94 (m, 2H), 2.41 (s, 3H), 1.25 (m, 3H).

[0227] Example 23: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-4-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid (compound number 17) [ka] A mixture of dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane complex (1:1) (0.054 g, 0.123 mmol), tripotassium phosphate (0.281 g, 1.33 mmol), (2-fluoro-4-pyridyl)boronic acid (0.094 g, 0.66 mmol), and 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxopyridine-3-carboxylic acid (150 mg, 0.33 mmol) was mixed with a mixture of degassed 1,2-dimethoxyethane (2.0 mL) and water (0.51 mL) at room temperature under a nitrogen atmosphere. The reaction mixture was heated at 120 °C for 0.75 hours under microwave irradiation. The cooled reaction mixture was diluted with water and then freeze-dried overnight. The crude residue was extracted with dichloromethane, filtered, and evaporated under reduced pressure until dry. The crude residue was purified by reverse-phase HPLC to obtain 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-4-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid (0.031 g, 0.073 mmol, 22%) as a brown solid. 1 ¹H NMR (400 MHz, chloroform): δ = 8.35 (d, 1H), 7.59 (d, 1H), 7.40 (s, 1H), 7.17-7.12 (m, 2H), 6.89 (s, 1H), 3.94 (br m, 2H), 2.41 (s, 3H), 1.24 (t, 3H).

[0228] Example 24: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-pyridine-1-ium-4-ylpyridine-3-carboxylic acid; 2,2,2-trifluoroacetate (compound number 25) [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid, preparations were made using 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (0.100 g, 0.24 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.152 g, 0.74 mmol). Purification by reverse-phase HPLC in the presence of trifluoroacetic acid yielded 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-pyridine-1-ium-4-ylpyridine-3-carboxylic acid 2,2,2-trifluoroacetate (0.054 g, 0.104 mmol, 42%) as a white solid. 1 ¹H NMR (400MHz, methanol-d4): δ = 8.89 (d, 2H), 7.92 (d, 2H), 7.73 (d, 1H), 7.67 (d, 1H), 7.38 (m, 1H), 4.04 (q, 2H), 2.48 (s, 3H), 1.24 (t, 3H).

[0229] Example 25: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-[4-(trifluoromethyl)phenyl]pyridine-3-carboxylic acid (compound number 26) [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxo-pyridine-3-carboxylic acid, 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-pyridine-3-carboxylic acid (100 mg, 0.25 mmol) and [4-(trifluoromethyl)phenyl]boronic acid (0.143 g, 0.75 mmol) were used to obtain 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-[4-(trifluoromethyl)phenyl]pyridine-3-carboxylic acid (0.030 g, 0.064 mmol, 26%). 1¹H NMR (500MHz, methanol-d4): δ = 7.81 (d, 2H), 7.71 (d, 1H), 7.67 (d, 1H), 7.50 (d, 2H), 7.37 (m, 1H), 4.03 (q, 2H), 2.43 (s, 3H), 1.23 (t, 3H).

[0230] Example 26: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-oxazol-2-yl-4-oxopyridine-3-carboxylic acid (compound number 27) Step 1: Synthesis of methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-oxazol-2-yl-4-oxopyridine-3-carboxylate [ka] To a mixture of methyl 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxopyridine-3-carboxylate (150 mg, 0.32 mmol) and tetrakis(triphenylphosphine)palladium(0) (0).075 g, 0.064 mmol, degassed toluene (1.3 mL) was added at room temperature under a nitrogen atmosphere, followed by dropwise addition of tributyl(oxazole-2-yl)stanan (0.27 g, 0.76 mmol). The reaction mixture was heated at 100°C for 18 hours with stirring. The cooled reaction mixture was evaporated under reduced pressure until dry. The crude residue was purified by reverse-phase HPLC to obtain methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-oxazole-2-yl-4-oxopyridine-3-carboxylate (0.050 g, 0.12 mmol, 38%) as a white solid. 1 ¹H NMR (400 MHz, chloroform): δ = 8.09 (s, 1H), 7.77-7.72 (m, 2H), 7.46 (m, 1H), 7.38 (s, 1H), 3.95 (q, 2H), 3.51 (s, 3H), 2.43 (s, 3H), 1.19 (t, 3H).

[0231] Step 2: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-oxazol-2-yl-4-oxopyridine-3-carboxylic acid [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-(3-pyridyl)pyridine-3-carboxylic acid, methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-oxazole-2-yl-4-oxopyridine-3-carboxylate (0.040 g, 0.098 mmol) and lithium hydroxide (0.033 g, 0.79 mmol) were used and heated at 80°C for 18 hours to prepare 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-oxazole-2-yl-4-oxopyridine-3-carboxylic acid (0.020 g, 0.050 mmol, 51%) as a white solid. 1 ¹H NMR (400MHz, methanol-d4): δ = 8.13 (d, 1H), 7.72-7.68 (m, 2H), 7.42-7.37 (m, 2H), 4.00 (q, 2H), 2.49 (s, 3H), 1.21 (t, 3H).

[0232] Example 27: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-pyridine-1-ium-2-ylpyridine-3-carboxylic acid chloride (compound number 28) Step 1: Synthesis of methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-(2-pyridyl)pyridine-3-carboxylate [ka] Similar to methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-oxazole-2-yl-4-oxopyridine-3-carboxylate, methyl 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxopyridine-3-carboxylate (0.100 g, 0.215 mmol) and tributyl(2-pyridyl)stanan (0.110 g, 0.32 mmol) were used to prepare methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-(2-pyridyl)pyridine-3-carboxylate (0.060 g, 0.144 mmol, 67%) as a brown oil. 1 ¹H NMR (400MHz, chloroform): δ = 9.18 (br m, 1H), 8.95 (d, 1H), 8.42 (m, 1H), 7.98 (d, 1H), 7.85 (t, 1H), 7.62 (d, 1H), 7.57 (d, 1H), 7.32 (m, 1H), 3.91 (q, 2H), 3.52 (s, 3H), 2.39 (s, 3H), 1.23 (t, 3H).

[0233] Step 2: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-pyridine-1-ium-2-ylpyridine-3-carboxylic acid chloride [ka] Similar to 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-pyridine-3-carboxylic acid, methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-(2-pyridyl)pyridine-3-carboxylate (0.030 g, 0.072 mmol) and lithium hydroxide monohydrate (0.024 g, 0.58 mmol) were used and heated at 80°C for 18 hours to prepare 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-pyridine-1-ium-2-yl-pyridine-3-carboxylic acid chloride (0.012 g, 0.0275 mmol, 38%). 1¹H NMR (400MHz, chloroform): δ = 8.84 (s, 1H), 8.28 (br m, 1H), 7.85 (br m, 1H), 7.75 (br m, 1H), 7.63 (d, 1H), 7.43 (s, 1H), 7.19 (d, 1H), 4.72 (br m, 1H), 3.97 (q, 2H), 2.58 (s, 3H), 1.33 (t, 3H).

[0234] Example 28: Synthesis of 2,5-bis(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (compound number 29) [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid, 2,5-bis(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (0.200 g, 0.493 mmol) and (3,4-dichlorophenyl)boronic acid (0.283 g, 1.48 mmol) were used to prepare 2,5-bis(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (0.115 g, 0.243 mmol, 49%) as an off-white solid. 1 ¹H NMR (400 MHz, chloroform): δ = 7.62-7.57 (m, 2H), 7.40-7.37 (m, 2H), 7.17-7.10 (m, 2H), 3.94 (q, 2H), 2.43 (s, 3H), 1.25 (t, 3H).

[0235] Example 29: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-(3-thienyl)pyridine-3-carboxylic acid (compound number 30) [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid, 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (0.200 g, 0.494 mmol) and (2-fluoro-3-pyridyl)boronic acid (0.209 g, 1.481 mmol) were heated at 100°C for 1 hour under microwave irradiation to obtain 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-(3-thienyl)pyridine-3-carboxylic acid (0.023 g, 0.0537 mmol, 11%) as a white solid. 1 ¹H NMR (400 MHz, chloroform): δ = 8.36-8.35 (m, 1H), 7.85 (m, 1H), 7.63 (m, 1H), 7.45-7.37 (m, 2H), 7.18 (m, 1H), 4.01-3.95 (m, 2H), 2.45 (d, 3H), 3.10 (t, 3H).

[0236] Example 30: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-(o-tolyl)-4-oxopyridine-3-carboxylic acid (compound number 31) [ka] A mixture of 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxopyridine-3-carboxylic acid (0.117 g, 0.259 mmol), tribasic potassium phosphate (0.165 g, 0.776 mmol), chloro(2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) (SPhos Pd G2, 0.043 g, 0.0518 mmol), and o-trilboronic acid (0.359 g, 2.59 mmol) was stirred at room temperature for 18 hours in a degassed mixture in 1,4-dioxane (1.8 mL) and water (0.4 mL). The reaction mixture was diluted with water and then freeze-dried. The crude residue was extracted with dichloromethane, filtered, and evaporated under reduced pressure until dry. The crude residue was purified by reverse-phase HPLC to obtain 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-(o-tolyl)-4-oxopyridine-3-carboxylic acid (0.043 g, 0.104 mmol, 40%). 1 ¹H NMR (400 MHz, chloroform): δ = 7.62 (m, 1H), 7.45 (m, 1H), 7.36-7.30 (m, 3H), 7.21 (m, 1H), 7.08-7.06 (m, 1H), 3.96 (q, 2H), 2.34 (s, 3H), 2.15 (d, 3H), 1.25 (t, 3H).

[0237] Example 31: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-(4-methylsulfonylphenyl)-4-oxopyridine-3-carboxylic acid (compound number 32) [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid, 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (0.200 g, 0.494 mmol) and (4-methylsulfonylphenyl)boronic acid (0.296 g, 1.48 mmol) were used to prepare 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-(4-methylsulfonylphenyl)-4-oxopyridine-3-carboxylic acid (0.073 g, 0.141 mmol, 31%) as a white solid. 1 H NMR (500MHz, DMSO-d6): δ=8.05(d,2H),7.83-7.79(m,2H),7.57-7.53(m,2H),7.47(m,1H),3.91(q,2H),3.26(s,3H),2.38(s,3H),1.14(t,3H).

[0238] Example 32: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-5-(3-furyl)-6-methyl-4-oxopyridine-3-carboxylic acid (compound number 33) [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid, 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (0.100 g, 0.247 mmol) and 3-furylboronic acid (0.083 g, 0.74 mmol) were used to prepare 2-(3,4-dichlorophenyl)-1-ethyl-5-(3-furyl)-6-methyl-4-oxopyridine-3-carboxylic acid (0.032 g, 0.082 mmol, 33%) as a brown oil. 1¹H NMR (400 MHz, chloroform): δ = 7.61-7.59 (m, 3H), 7.38 (d, 1H), 7.14 (m, 1H), 6.50-6.49 (m, 1H), 3.96 (q, 2H), 2.61 (s, 3H), 1.24 (t, 3H).

[0239] Example 33: Synthesis of 5-(4-benzyloxyphenyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (compound number 35) [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid, 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (0.200 g, 0.494 mmol) and 4-benzyloxyphenylboronic acid (0.345 g, 1.48 mmol) were used to prepare 5-(4-benzyloxyphenyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (0.079 g, 0.156 mmol, 32%) as an off-white solid. 1 ¹H NMR (400MHz, chloroform): δ = 7.61 (d, 1H), 7.48-7.46 (m, 2H), 7.43-7.39 (m, 3H), 7.37-7.33 (m, 1H), 7.19-7.16 (m, 3H), 7.12-7.10 (m, 2H), 5.12 (s, 2H), 3.94 (q, 2H), 2.44 (s, 3H), 1.25 (t, 3H).

[0240] Example 34: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-pyridazin-4-ylpyridine-3-carboxylic acid; 2,2,2-trifluoroacetic acid (compound number 35) [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid, 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (0.100 g, 0.247 mmol) and pyridazine-4-ylboronic acid (0.092 g, 0.74 mmol) were used to prepare 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxo-5-pyridazine-4-ylpyridine-3-carboxylic acid; 2,2,2-trifluoroacetic acid (0.050 g, 0.096 mmol, 39%) as a white solid. 1 ¹H NMR (400MHz, methanol-d4): δ = 9.38 (d,1H), 9.25 (br m,1H), 7.87 (d,1H), 7.72 (d,1H), 7.67 (d,1H), 7.37 (m,1H), 4.04 (q,2H), 2.49 (s,3H), 1.24 (t,3H).

[0241] Example 35: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-(4-nitrophenyl)-4-oxopyridine-3-carboxylic acid (compound number 36) Step 1: Synthesis of methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-(4-nitrophenyl)-4-oxopyridine-3-carboxylate [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid, methyl 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (0.250 g, 0.597 mmol) and (4-nitrophenyl)boronic acid (0.149 g, 0.895 mmol) were used to prepare methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-(4-nitrophenyl)-4-oxopyridine-3-carboxylate (0.179 g, 0.388 mmol, 65%) as an orange solid. 1 ¹H NMR (400 MHz, chloroform): δ = 7.59-7.52 (m, 2H), 7.46-7.36 (m, 4H), 7.24-7.15 (m, 2H), 3.98-3.86 (m, 3H), 2.50-2.31 (m, 2H), 0.87-0.60 (m, 3H).

[0242] Step 2: Synthesis of 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-(4-nitrophenyl)-4-oxopyridine-3-carboxylic acid [ka] Similar to 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid, methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-(4-nitrophenyl)-4-oxopyridine-3-carboxylate (0.179 g, 0.388 mmol) was used to prepare 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-(4-nitrophenyl)-4-oxopyridine-3-carboxylic acid (0.055 g, 0.123 mmol, 32%) as an off-white powder. 1H NMR(400MHz,DMSO-d6)δ=8.40-8.27(m,2H),7.84-7.77(m,2H),7.62-7.53(m,2 H),7.49-7.41(m,1H),3.96-3.79(m,2H),2.42-2.36(m,3H),1.18-1.03(m,3H).

[0243] Example 36: Synthesis of 5-(5-chloro-3-thienyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (compound number 37) [ka] Similar to 2-(3,4-dichlorophenyl)-1-ethyl-5-(2-fluoro-3-pyridyl)-6-methyl-4-oxopyridine-3-carboxylic acid, 5-bromo-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (0.200 g, 0.494 mmol) and (5-chloro-3-thienyl)boronic acid (0.241 g, 1.481 mmol) were used and heated at 100°C for 18 hours to prepare 5-(5-chloro-3-thienyl)-2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-4-oxopyridine-3-carboxylic acid (0.102 g, 0.23 mmol, 47%) as an off-white solid. 1 ¹H NMR (400 MHz, chloroform): δ = 7.59 (d, 1H), 7.39 (d, 1H), 7.15 (m, 1H), 7.08 (d, 1H), 6.91 (d, 1H), 3.93 (q, 2H), 2.51 (s, 3H), 1.24 (t, 3H).

[0244] Examples 37 and 38: Synthesis of methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-(3-methylimidazole-4-yl)-4-oxopyridine-3-carboxylate (compound number 39) and 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-(3-methylimidazole-4-yl)-4-oxopyridine-3-carboxylic acid (compound number 40) [ka] Similar to methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-oxazol-2-yl-4-oxopyridine-3-carboxylate, the following preparations were made using methyl 2-(3,4-dichlorophenyl)-1-ethyl-5-iodo-6-methyl-4-oxopyridine-3-carboxylate (0.150 g, 0.322 mmol) and 1-methyl-5-(tributylstanyl)imidazole (0.189 g, 0.483 mmol), and then subjected to mass spectrometry. After purification by reverse-phase HPLC, methyl 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-(3-methylimidazole-4-yl)-4-oxopyridine-3-carboxylate (0.019 g, 0.045 mmol, 14%) and 2-(3,4-dichlorophenyl)-1-ethyl-6-methyl-5-(3-methylimidazole-4-yl)-4-oxopyridine-3-carboxylic acid (0.019 g, 0.046 mmol, 14%) were obtained. 1 ¹H NMR (400 MHz, chloroform): δ = 7.65-7.54 (m, 3H), 7.37-7.26 (m, 1H), 7.24 (d, 1H), 3.91-3.84 (m, 2H), 3.80 (s, 3H), 3.56 (d, 3H), 2.47 (s, 3H), 1.23 (m, 3H). 1 ¹H NMR (400MHz, methanol-d4): δ = 7.78 (d, 1H), 7.76-7.74 (m, 2H), 7.71 (m, 1H), 7.74-7.70 (m, 1H), 4.08-3.96 (m, 2H), 3.81 (s, 3H), 2.45 (s, 3H), 1.23 (t, 3H).

[0245] [Table 6-1] [Table 6-2] [Table 6-3] [Table 6-4] Table 6-5 Table 6-6 Table 6-7 Table 6-8 Table 6-9 Table 6-10 Table 6-11 Table 6-12 Table 6-13 Table 6-14 Table 6-15 Table 6-16 Table 6-17 Table 6-18 Table 6-19 Table 6-20 Table 6-21 Table 6-22 Table 6-23 Table 6-24 Table 6-25 Table 6-26 Table 6-27 Table 6-28 Table 6-29 Table 6-30 Table 6-31 Table 6-32 Table 6-33 Table 6-34 Table 6-35 Table 6-36 Table 6-37 Table 6-38 Table 6-39 Table 6-40 Table 6-41 Table 6-42 Table 6-43 Table 6-44 Table 6-45 Table 6-46 Table 6-47 Table 6-48 Table 6-49 Table 6-50 Table 6-51 Table 6-52 Table 6-53 Table 6-54 Table 6-55 Table 6-56 Table 6-57 Table 6-58 Table 6-59 Table 6-60 Table 6-61 Table 6-62 Table 6-63 Table 6-64 Table 6-65 Table 6-66 Table 6-67 Table 6-68 Table 6-69 Table 6-70 Table 6-71 Table 6-72 Table 6-73 Table 6-74 Table 6-75 Table 6-76 Table 6-77 Table 6-78 Table 6-79 Table 6-80 Table 6-81 Table 6-82 Table 6-83 Table 6-84

[0246] examples of biology Seeds of various test species were sown in standard soil in pots (Amaranthus retoflexus (AMARE), Solanum nigrum (SOLNI), Setaria faberi (SETFA), Lolium perenne (LOLPE), Echinochloa crus-galli (ECHCG), Ipomoea hederacea (IPOHE), Abutilon theophrasti (ABUTH), Zea mays (ZEAMX), Amaranthus palmeri (AMAPA). After being grown for 8 days in a greenhouse under controlled conditions (24°C / 16°C, day / night; 14 hours of light; 65% humidity), the plants were 0.5% tween. A spray solution derived from a formulation of industrial active ingredients in an acetone / water (50:50) solution containing 20 (polyoxyethylene sorbitan monolaurate, CAS RN 9005-64-5) was sprayed onto plants. Unless otherwise specified, the compound was applied at a rate of 1000 g / ha. Test plants were then grown in a greenhouse under controlled conditions (24°C / 16°C, day / night; 14 hours of light; 65% humidity) and watered twice daily. After 13 days, the test was evaluated for the percentage of damage caused by the plants. Biological activity is shown in the following table on a 5-point scale (5 = 81-100%; 4 = 61-80%; 3 = 41-60%; 2 = 21-40%; 1 = 0-20%).

[0247] [Table 7-1] [Table 7-2] [Table 7-3] [Table 7-4] [Table 7-5]

[0248] Table 8-1 Table 8-2 Table 8-3 Table 8-4 Table 8-5

Claims

1. Compound of formula (I): 【Chemistry 1】 (In the formula, X is O, NR 6 or S; R 1 is C 1 ~C 6 It is alkyl; R 2 R is phenyl or pyridyl, and each phenyl and pyridyl portion is R 7 It may be arbitrarily substituted with one, two, three, or four bases, which may be identical or different, represented by; R 3 is hydrogen, C 1 to C 6 alkyl, N,N - di(C 1 to C 3 alkyl)amino, C 1 to C 6 haloalkyl, C 3 to C 6 cycloalkyl, C 3 to C 6 cycloalkyl C 1 to C 6 alkyl, C 1 to C 6 alkoxy C 1 to C 6 alkyl, C 2 to C 6 alkenyl, or C 2 to C 6 alkynyl, and; R 4 is cyclopentenyl, phenyl, styryl, or heteroaryl (where the heteroaryl portion is a five-membered or six-membered aromatic monocyclic ring containing one or two heteroatoms individually selected from N, O, and S), where the phenyl and heteroaryl portions are each R 9 It may be arbitrarily substituted with one, two, or three bases, which may be identical or different, represented by; R 5 C 1 ~C 4 Alkyl or C 1 ~C 4 Alkoxy C 1 ~C 4 It is alkyl; R 6 is hydrogen, C 1 ~C 3 Alkyl or C 1 ~C 6 It is an alkoxy; R 7 These are cyano, nitro, halogen, and C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Haloalkyl, C 1 ~C 6 Haloalkoxy, C 1 ~C 6 Alkoxy C 1 ~C 6 Alkyl, C 1 ~C 6 Alkyl sulfanyl, C 1 ~C 6 Alkyl sulfinyl, C 1 ~C 6 Alkyl sulfonyl, C 1 ~C 6 Alkyl sulfonamide, C 1 ~C 6 Alkylcarbonyl, C 1 ~C 6 Alkoxycarbonyl, C 1 ~C 6 It is an alkylaminocarbonyl or phenyl, and each phenyl portion is R 10 It may be arbitrarily substituted with one, two, or three bases, which may be identical or different, represented by; R 9 is cyano, nitro, halogen, oxo, C 1 to C 6 alkyl, C 1 to C 6 alkoxy, C 1 to C 6 haloalkyl, C 1 to C 6 haloalkoxy, C 1 to C 6 alkoxyC 1 to C 6 alkyl, C 1 to C 6 alkoxyC 1 to C 6 alkoxy, C 2 to C 6 alkenyl, C 2 to C 6 alkynyl, C 2 to C 6 alkenyloxy, C 2 to C 6 alkynyloxy, C 1 to C 6 alkylsulfanyl, C 1 to C[[ID=​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​The alkyl)aminocarbonyl, phenoxy, or benzyloxy moiety is R 12 It may be arbitrarily substituted with one or two bases, which may be identical or different, represented by; or Any two adjacent R 9 The groups, together with the carbon atoms to which they are bonded, can form a five-membered or six-membered heterocyclyl ring containing one or two heteroatoms selected from O and N, wherein the heterocyclyl ring is R 11 It may be arbitrarily substituted with one, two, three, or four bases, which may be identical or different, represented by; R 10 is halogen, C 1 ~C 3 Alkyl or C 1 ~C 3 It is an alkoxy; R 11 is halogen, C 1 ~C 3 Alkyl or C 1 ~C 3 It is an alkoxy; R 12 These are cyano, halogen, and C 1 ~C 3 Alkyl or C 1 ~C 3 (It is an alkoxy) Or, its salt or N-oxide.

2. R 1 is C 1 ~C 4 The compound according to claim 1, wherein it is alkyl.

3. R 2 R is phenyl or pyridyl, and each phenyl and pyridyl portion is R 7 The compound according to claim 1 or claim 2, which may be optionally substituted with one or two groups that are identical or different and represented by .

4. R 3 is hydrogen, C 1 ~C 4 Alkyl or N,N-di(C) 1 ~C 3 A compound according to any one of claims 1 to 3, wherein it is an alkyl)amino.

5. R 4 is a phenyl or heteroaryl compound (where the heteroaryl portion is a five-membered or six-membered aromatic monocyclic ring containing one or two heteroatoms individually selected from N, O, and S), where the phenyl and heteroaryl portions are each R 9 The compound according to any one of claims 1 to 4, which may be optionally substituted with one or two groups that are identical or different and represented by .

6. R 5 C 1 ~C 3 Alkyl or C 1 ~C 2 Alkoxy C 1 ~C 2 A compound according to any one of claims 1 to 5, wherein it is alkyl.

7. The compound according to any one of claims 1 to 6, wherein R 7 is chloro, fluoro, bromo, or 2,4-difluorophenyl.

8. R 9 These are cyano, nitro, halogen, oxo, and C. 1 ~C 4 Alkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkoxy C 1 ~C 4 Alkyl, C 1 ~C 4 Alkoxy C 1 ~C 4 Alkoxy, C 1 ~C 4 Alkyl sulfanyl, C 1 ~C 4 Alkyl sulfonyl, C 1 ~C 4 Alkyl sulfonamide, C 1 ~C 4 Alkylcarbonyl, C 1 ~C 4 Alkoxycarbonyl, C 3 ~C 4 Cycloalkyl, C 3 ~C 4 Cycloalkyl C 1 ~C 3 Alkoxy, N,N-di(C) 1 ~C 3 Alkyl)aminosulfonyl, C 3 ~C 4 Cycloalkylaminocarbonyl, N,N-di(C 1 ~C 3 The alkyl)aminocarbonyl, phenoxy, or benzyloxy moiety is R 12 It may be arbitrarily substituted with one or two bases, which may be identical or different, represented by; or Any two adjacent R 9 The groups, together with the carbon atoms to which they are bonded, can form a five-membered or six-membered heterocyclyl ring containing one or two heteroatoms selected from O and N, wherein the heterocyclyl ring is R 11 The compound according to any one of claims 1 to 7, which may be optionally substituted with one or two groups that are identical or different and represented by .

9. R 9 These are cyano, nitro, chloro, fluoro, oxo, methyl, t-butyl, methoxy, ethoxy, isopropoxy, difluoromethyl, trifluoromethyl, trifluoromethoxy, 2,2,2-trifluoroethoxy, methoxymethyl, methoxyethoxy, methylsulfanyl, methylsulfonyl, ethylsulfonyl, acetyl, cyclopropylmethoxy, ethylcarbamoyl, cyclopropylcarbamoyl, dimethylcarbamoyl, diethylsulfamoyl, phenoxy, benzyloxy; or any two adjacent R 9 The compound according to any one of claims 1 to 8, wherein the groups, together with the carbon atoms to which they are bonded, can form a five-membered heterocyclyl ring containing two oxygen atoms, and the heterocyclyl ring may be optionally substituted with one or two fluoro groups.

10. A herbicide composition comprising the compound described in any one of claims 1 to 9 and an agriculturally acceptable compounding agent.

11. The herbicide composition according to claim 10, further comprising at least one additional pesticide.

12. The herbicide composition according to claim 11, wherein the additional pesticide is a herbicide or a herbicide toxicity mitigator.

13. A method for controlling weeds in a habitat, comprising the step of applying a control amount of the composition described in any one of claims 10 to 12 to the habitat of the weeds.

14. Use of a compound of formula (I) according to any one of claims 1 to 9 as a herbicide.

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