Herbicide alanine analog

Abstract

The present invention relates to a compound of formula (I) [wherein the formula the variables are as defined in the claims and herein], the use of the alanine analog for controlling undesirable vegetation, and a method for applying the alanine analog. [Formula 1] TIFF2026527520000104.tif21170

Description

[Technical Field]

[0001] This invention relates to specific alanine analogs and the use of such alanine analogs for controlling undesirable vegetation. Furthermore, this invention relates to methods for applying alanine analogs. [Background technology]

[0002] In particular, there is a continuous need for novel herbicides that are virtually non-toxic to humans and animals, yet possess high activity and selectivity, to control undesirable vegetation in crops.

[0003] International publications No. 2023 / 025855, No. 2022 / 112347, and No. 2023 / 025854 describe alkyl-substituted malonamide compounds and their use as herbicides.

[0004] Conventional compounds often exhibit unsatisfactory selectivity, resulting in insufficient herbicidal activity and / or poor compatibility with crop plants, particularly at low application rates.

[0005] N-(benzoyl)-alanine derivatives and specific N-(benzoyl)-alanine derivatives containing a second amino acid moiety, as well as methods for their preparation, are known, for example, from Saavedra, Carlos; Hernandez, Rosendo; Boto, Alicia; Alvarez, Eleuterio J. Org. Chem. 2009, 74, 4655-65. No biological activity, such as herbicidal activity, has been reported for these compounds. [Overview of the project] [Problems that the invention aims to solve]

[0006] Therefore, an object of the present invention is to provide further herbicidal compounds that have strong herbicidal activity even at low application rates, have sufficiently low toxicity to humans and animals, and / or are highly compatible with crop plants. The compounds should also exhibit a broad activity spectrum against a number of different undesirable plants. [Means for solving the problem]

[0007] These and further objectives are achieved by compounds of formula (I) as defined below, including their agriculturally acceptable salts, stereoisomers, and tautomers.

[0008] Therefore, the present invention relates to formula (I) [ka] [In the formula, the substituents have the following meanings: R 1 , R 8 These are, independently of each other, hydrogen, (C1~C3)-alkyl, (C1~C3)-haloalkyl, (C3~C4)-cycloalkyl, (C2~C3)-alkenyl, (C2~C3)-haloalkenyl, (C3~C4)-alkynyl, (C3~C4)-haloalkynyl, (C1~C3)-alkoxy-(C1~C3)-alkyl, aryl, aryl-(C1~C3)-alkyl, (C1~C3)-alkoxy, (C1~C3)-haloalkoxy, (C1~C3)-alkoxy-(C1~C3)-alkoxy, (C1~C3)-alkylcarbonyl, arylcarbonyl, (C1~C3)-alkoxycarbonyl, or aryloxycarbonyl; R 2 , R 6 These are, independently of each other, hydrogen, halogen, hydroxyl, cyano, (C1~C3)-alkyl, (C1~C3)-haloalkyl, (C1~C3)-alkoxy, or (C1~C3)-haloalkoxy; R 3 , R 5are, independently of one another, hydrogen, halogen, nitro, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C5)-cycloalkyl, (C3-C5)-halocycloalkyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy, (C1-C3)-alkoxycarbonyl, (C1-C3)-haloalkoxycarbonyl, (C1-C3)-alkylthio, (C1-C3)-haloalkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-haloalkylsulfinyl, (C1-C3)-alkylsulfonyl, (C1-C3)-haloalkylsulfonyl, or (C1-C3)-dialkylamino; R 4 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C4)-cycloalkyl, (C3-C4)-halocycloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C1-C3)-dialkylamino, or (C1-C3)-alkylthio; R 7 is methyl or ethyl; R 9 is hydrogen; X is oxygen or sulfur; Q is of the formula (Z-Y)

Chemical formula

[0009] The present invention also relates to a composition comprising at least one compound of formula (I) and at least one adjuvant commonly used to formulate crop protection compounds.

[0010] The present invention also provides combinations comprising at least one compound of formula (I) (component A) and an antidote C (component C).

[0011] The present invention further relates to the use of compounds of formula (I) for controlling undesirable vegetation, and to a method for controlling undesirable vegetation, comprising applying an effective herbicidal amount of at least one compound of formula (I) to plants, their seeds, and / or their habitat. [Modes for carrying out the invention]

[0012] Definition: Depending on the type of substituent, a compound of formula (I) may have one or more chiral centers, in which case the compound may exist as a mixture of enantiomers or diastereomers, but may also exist in the form of a pure enantiomer or pure diastereomer. The present invention provides both pure enantiomers or pure diastereomers and mixtures thereof of compounds of formula I, as well as the use of pure enantiomers or pure diastereomers or mixtures thereof of compounds of formula I according to the present invention. Suitable compounds of formula I also include all possible geometric stereoisomers (cis / trans isomers) and mixtures thereof, as specific forms of diastereomers and mixtures thereof. Cis / trans isomers may exist with respect to alkenes, carbon-nitrogen double bonds, nitrogen-sulfur double bonds, amide groups, or cyclic non-aromatic moieties. The term “stereoisomer” encompasses both optical isomers such as enantiomers or diastereomers (the latter existing due to the presence of one or more stereoisomeric centers in the molecule), and geometric isomers (cis / trans isomers). As just one example, stereoisomers are R 7 and R 9 It is a carbon atom that possesses [a certain characteristic].

[0013] If the aforementioned antidote C has one or more chiral centers, they may also exist as enantiomers or diastereomers, and it is possible to use both pure enantiomers and pure diastereomers or mixtures thereof.

[0014] If the compounds of formula (I) described herein, or antidote C, have ionizable functional groups, they may also be used in the form of agrochemically acceptable salts. Generally, salts of their cations and anions, and acid addition salts of their acids, are preferred, such that their cations and anions do not adversely affect the activity of the active compound, respectively.

[0015] Preferred cations include alkali metals, preferably lithium, sodium, and potassium ions; alkaline earth metals, preferably calcium and magnesium ions; and transition metals, preferably manganese, copper, zinc, and iron ions. Furthermore, ammonium and substituted ammonium in which 1 to 4 hydrogen atoms are substituted with C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl, or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, diisopropylammonium, trimethylammonium, triethylammonium, tris(isopropyl)ammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetramethylammonium, tetramethylammonium These include tris(2-hydroxyethylammonium), tetrabutylammonium, 2-hydroxyethylammonium (olamine salt), 2-(2-hydroxyethanol-1-oxy)ethanol-1-ylammonium (diglycolamine salt), di(2-hydroxyethanol-1-yl)ammonium (diolamine salt), tris(2-hydroxyethyl)ammonium (trolamine salt), tris(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), as well as phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, for example, trimethylsulfonium and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium, and finally salts of polybasic amines such as N,N-bis-(3-aminopropyl)methylamine and diethylenetriamine.

[0016] Useful anions for acid addition salts are mainly chloride, bromide, fluoride, iodide, bisulfate, methylsulfate, sulfuric acid, dihydrogen phosphate, hydrogen phosphate, nitric acid, bicarbonate, carbonic acid, hexafluorosilicic acid, hexafluorophosphate, and benzoate anions, as well as anions of C1-C4 alkanic acids, preferably formic acid, acetic acid, propionic acid, and butyrate anions.

[0017] If a compound of formula (I) can form tautomers by intramolecular proton transfer, these tautomers are also included in the definition and fall within the scope of general formula (I) according to the present invention. Common examples of such interconversions include, in particular, keto-enol-(HOC=C⇔O=CCH) and amide-imoid acid-(HNC=O⇔N=COH) tautomerisms. The amount of one or more tautomers present depends on the complete molecular structure and is also strongly dependent on the surrounding conditions (presence or absence of solvent, type of solvent, pH, temperature, etc.).

[0018] The term “undesirable vegetation” (“weeds”) is understood to include all vegetation growing on non-agricultural land or at crop plant sites or locations of sown crops and other desired crops. Vegetation includes all vegetation other than (if present) sown crops or desired crops, including their germinating seeds, emerging seedlings, and established vegetation. In a broad sense, weeds are plants that are considered undesirable in a particular location.

[0019] The organic part, as defined in the above definition of variable elements, is a general term that encompasses a list of each individual member of that group, similar to the term halogen. n ~C m The prefix "-" in each case indicates the number of carbon atoms that can be present in the base.

[0020] The term "halogen" in each case means fluorine, bromine, chlorine, or iodine, and in particular means fluorine, chlorine, or bromine.

[0021] The term "partially or fully halogenated" means that one or more hydrogen atoms of a given group, for example, one, two, three, four, five, or all of them, are substituted with halogen atoms, particularly fluorine or chlorine. Partially or fully halogenated groups are also hereafter referred to as "halo groups." For example, partially or fully halogenated alkyl groups are also called haloalkyl groups.

[0022] As used herein, the term "alkyl" (and other groups containing alkyl groups, such as alkoxy, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, and the alkyl portion of alkoxyalkyl) typically refers to groups with 1 to 12 carbon atoms (=C1-C12) in each case. 12 C1-C2-alkyl groups often have 1 to 6 carbon atoms (=C1-C6-alkyl groups), especially 1 to 4 carbon atoms (=C1-C4-alkyl groups), especially 1 to 3 carbon atoms (=C1-C3-alkyl groups), or 1 or 2 carbon atoms (=C1-C2-alkyl groups), representing linear or branched alkyl groups. C1-C2-alkyl groups are methyl or ethyl. C1-C3-alkyl groups are methyl, ethyl, n-propyl, or isopropyl. Examples of C1-C4-alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl (=sec-butyl), isobutyl, and tert-butyl. Examples of C1-C6 alkyl groups, in addition to those described for C1-C4 alkyl groups, include n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, and 1-ethyl-2-methylpropyl. Examples of C1-C8 alkyl groups, in addition to those mentioned for C1-C6 alkyl groups, include n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, n-octyl, 1-methylheptyl, 2-methylheptyl, 1-ethylhexyl, 2-ethylhexyl, 1,2-dimethylhexyl, 1-propylpentyl, and 2-propylpentyl.12 Examples of alkyl groups, in addition to those mentioned for C1-C8 alkyl groups, include nonyl, decyl, 2-propylheptyl, 3-propylheptyl, undecyl, dodecyl, and their positional isomers.

[0023] As used herein, the term “haloalkyl” (and the haloalkyl portion of other groups containing haloalkyls, e.g., haloalkoxy, haloalkylthio, haloalkylcarbonyl, haloalkylsulfonyl, and haloalkylsulfinyl) is also expressed as “partially or completely halogenated alkyl,” in each case referring to a linear or branched alkyl group having typically 1 to 6 carbon atoms (=C1-C6-haloalkyl), more often 1 to 3 carbon atoms (=C1-C3-haloalkyl), as defined above, in which the hydrogen atoms of the group are partially or completely substituted with halogen atoms. Preferred haloalkyl portions are selected from C1-C3-haloalkyls, particularly C1-C2-haloalkyls, and especially fluorinated C1-C2-alkyls. Examples of C1-C2 haloalkyls include fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, 1-chloroethyl, 2-chloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, and 1-bromoethyl. Examples of C1-C3 haloalkyls include those described for C1-C2 haloalkyls, as well as 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1,1,1-trifluoropropyl-2-yl, and 3-chloropropyl.

[0024] The term "hydroxyalkyl" in each case means an alkyl group that, as defined above, typically has 1 to 6 carbon atoms (=C1-C6-hydroxyalkyl), and more frequently has 1 to 3 carbon atoms (=C1-C3-hydroxyalkyl), where one hydrogen atom of the group is substituted with a hydroxyl group, and is either linear or branched. Examples include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, and 1-hydroxy-2-propyl.

[0025] As used herein, the term “alkenyl” typically refers to 2 to 12 alkenyls in each case (=C2 to C2). 12This refers to a monounsaturated linear or branched hydrocarbon group having 2 to 6 carbon atoms (=C2-C6-alkenyl), for example, 3 to 6 carbon atoms (=C3-C6-alkenyl), particularly 2 to 4 carbon atoms (=C2-C4-alkenyl), or 2 or 3 carbon atoms (=C2-C3-alkenyl), and a double bond at any position; for example, C2-C3-alkenyls such as ethenyl, 1-propenyl, 2-propenyl, or 1-methylethenyl; for example, C2-C4-alkenyls such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, or 2-methyl-2-propenyl;For example, ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3- Methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3- Pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2, C2-C6 alkenyls such as 3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, and 1-ethyl-2-methyl-2-propenyl;Or groups such as C2-C6 alkenyls, and further C2-C6 groups such as 1-heptenyl, 2-heptenyl, 3-heptenyl, 1-octenyl, 2-octenyl, 3-octenyl, 4-octenyl, nonenyl, decenyl, undecenyl, and dodecenyl; 12 -Alkenyl and its positional isomers.

[0026] Examples of C3-C6 alkenyls, with the exception of ethenyls, are those mentioned above for C2-C6 alkenyls.

[0027] As used herein, the term "haloalkenyl" is also expressed as "halogen-substituted alkenyl," and the haloalkenyl portion in haloalkenyloxy and the like refers to an unsaturated linear or branched hydrocarbon group having 2 to 6 (=C2-C6-haloalkenyl), 2 to 4 (=C2-C4-haloalkenyl), or 2 to 3 (=C2-C3-haloalkenyl) carbon atoms and a double bond at any position, wherein some or all of the hydrogen atoms of these groups are substituted with the above-mentioned halogen atoms, particularly fluorine, chlorine, and bromine, such as chlorovinyl and chloroallyl.

[0028] As used herein, the term "alkynyl" usually refers to 2 to 12 cells (=C2 to C2). 12C2-C3 alkynyl groups, frequently consisting of 2-6 (=C2-C6-alkynyl), preferably 2-4 carbon atoms (=C2-C4-alkynyl) or 2-3 carbon atoms (=C2-C3-alkynyl) and having triple bonds at any position, refer to unsaturated linear or branched hydrocarbon groups; for example, C2-C3 alkynyls such as ethynyl, 1-propynyl, or 2-propynyl; ethynyl, 1-propynyl, or 2-propynyl C2-C4 alkynyls such as nyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl; ethinyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-2-butynyl, 1-methyl-3-butynyl, 3-methyl-2-butynyl Tyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4- These are C2-C6 alkynyl compounds such as methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, and 1-ethyl-1-methyl-2-propynyl.

[0029] As used herein, the term "haloalkynyl" is also expressed as "halogen-substituted alkynyl," and refers to an unsaturated linear or branched hydrocarbon group (as described above) having typically 2 to 6 carbon atoms (=C2-C6-haloalkynyl), preferably 2 to 4 carbon atoms (=C2-C4-haloalkynyl), or 2 or 3 carbon atoms (=C2-C3-haloalkynyl) and a triple bond at any position, wherein some or all of the hydrogen atoms of these groups are substituted with the halogen atoms described above, particularly fluorine, chlorine, and bromine.

[0030] Where used herein (and in other groups including cycloalkyl groups, e.g., cycloalkoxys and the cycloalkyl portion of cycloalkylalkyls), the term “cycloalkyl” means, in each case, a monocyclic or bicyclic saturated cyclic aliphatic group having, typically, 3 to 8 carbon atoms (=C3-C8-cycloalkyl), preferably 3 to 6 carbon atoms (=C3-C6-cycloalkyl), 3 to 5 carbon atoms (=C3-C5-cycloalkyl), or 3 to 4 carbon atoms (=C3-C4-cycloalkyl) as its (sole) ring member.

[0031] Examples of monocyclic saturated aliphatic groups having 3 or 4 carbon atoms include cyclopropyl and cyclobutyl. Examples of monocyclic saturated aliphatic groups having 3 to 5 carbon atoms include cyclopropyl, cyclobutyl, and cyclopentyl. Examples of monocyclic saturated aliphatic groups having 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Examples of monocyclic saturated aliphatic groups having 3 to 8 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. C5-C6 cycloalkyl groups are cyclopentyl or cyclohexyl. Examples of bicyclic groups having 6 to 8 carbon atoms include bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, and bicyclo[3.2.1]octyl.

[0032] As used herein (and in the halocycloalkyl portion of other groups including halocycloalkyl groups), the term “halocycloalkyl” in each case refers to a monocyclic or bicyclic aliphatic group having typically 3 to 8 carbon atoms ("C3-C8-halocycloalkyl"), preferably 3 to 5 carbon atoms ("C3-C5-halocycloalkyl"), in which at least one hydrogen atom, e.g., 1, 2, 3, 4, or 5, is substituted with a halogen, particularly fluorine or chlorine. Examples include 1- and 2-fluorocyclopropyl, 1,2-, 2,2- and 2,3-difluorocyclopropyl, 1,2,2-trifluorocyclopropyl, 2,2,3,3-tetrafluorocyclicpropyl (cyclpropyl), 1- and 2-chlorocyclopropyl, 1,2-, 2,2- and 2,3-dichlorocyclopropyl, 1,2,2-trichlorocyclopropyl, 2,2,3,3-tetrachlorocyclicpropyl (cyclpropyl), 1-, 2- and 3-fluorocyclopentyl, 1,2-, 2,2-, 2,3-, 3,3-, 3,4-, and 2,5-difluorocyclopentyl, 1-, 2- and 3-chlorocyclopentyl, and 1,2-, 2,2-, 2,3-, 3,3-, 3,4-, and 2,5-dichlorocyclopentyl.

[0033] The term "hydroxycycloalkyl" refers to a monocyclic or bicyclic aliphatic group having typically 3 to 6 carbon atoms ("hydroxy-(C3-C6)-cycloalkyl"), preferably 3 to 5 carbon atoms ("hydroxy-(C3-C5)-cycloalkyl"), in each case, in which at least one hydrogen atom, e.g., 1, 2, 3, 4, or 5, is substituted with a hydroxyl group. Examples include 1-hydroxycyclopropyl, 2-hydroxycyclopropyl, 1,2-dihydroxycyclopropyl, 2,3-dihydroxycyclopropyl, 1-hydroxycyclobutyl, 2-hydroxycyclobutyl, 3-hydroxycyclobutyl, 1,2-dihydroxycyclobutyl, 1,3-dihydroxycyclobutyl, 2,3-dihydroxycyclobutyl, 1-hydroxycyclopentyl, 2-hydroxycyclopentyl, 3-hydroxycyclopentyl, 1,2-dihydroxycyclopentyl, 1,3-dihydroxycyclopentyl, 2,3-dihydroxycyclopentyl, and the like.

[0034] As used herein, the term “alkoxy” refers in each case to a linear or branched alkyl group having typically 1 to 6 carbon atoms (=C1-C6-alkoxy), preferably 1 to 3 carbon atoms (=C1-C3-alkoxy), and particularly 1 or 2 carbon atoms (=C1-C2-alkoxy), bonded to the remainder of the molecule via an oxygen atom. The C1-C2-alkoxy is methoxy or ethoxy. The C1-C3-alkoxy is further, for example, n-propoxy or 1-methylethoxy (isopropoxy). C1-C6 alkoxys also include, for example, butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy), or 1,1-dimethylethoxy (tert-butoxy), pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy. These are rupentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, or 1-ethyl-2-methylpropoxy.

[0035] As used herein, the term "haloalkoxy" means, in each case, a linear or branched alkoxy group having 1 to 6 carbon atoms (=C1-C6-haloalkoxy), preferably 1 to 3 carbon atoms (=C1-C3-haloalkoxy), particularly 1 or 2 carbon atoms (=C1-C2-haloalkoxy), as defined above, wherein the hydrogen atoms of the group are partially or entirely substituted with halogen atoms, particularly fluorine atoms (in this case, the group is also referred to as a fluorinated alkoxy). Examples of C1-C2 haloalkoxys include OCH2F, OCHF2, OCF3, OCH2Cl, OCHCl2, OCl3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, or OC2F5. C1-C3-haloalkoxys are further, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1-(CH2F)-2-fluoroethoxy, 1-(CH2Cl)-2-chloroethoxy, or 1-(CH2Br)-2-bromoethoxy. C1-C6-haloalkoxys are further, for example, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.

[0036] The term "alkenyloxy" refers to the alkenyl group defined above, which is bonded to the remainder of the molecule via an oxygen atom. C2-C6-alkenyloxy is the C2-C6-alkenyl group defined above, which is bonded to the remainder of the molecule via an oxygen atom. C3-C6-alkenyloxy is the C3-C6-alkenyl group defined above, which is bonded to the remainder of the molecule via an oxygen atom.

[0037] The term "haloalkenyloxy" refers to the haloalkenyl group defined above, which is bonded to the remainder of the molecule via an oxygen atom. C2-C6-haloalkenyloxy is the C2-C6-haloalkenyl group defined above, which is bonded to the remainder of the molecule via an oxygen atom. C3-C6-haloalkenyloxy is the C3-C6-haloalkenyl group defined above, which is bonded to the remainder of the molecule via an oxygen atom.

[0038] The term "alkynyloxy" refers to the alkynyl group defined above, which is bonded to the remainder of the molecule via an oxygen atom. C2-C6-alkynyloxy is the C2-C6-alkynyl group defined above, which is bonded to the remainder of the molecule via an oxygen atom. C3-C6-alkynyloxy is the C3-C6-alkynyl group defined above, which is bonded to the remainder of the molecule via an oxygen atom.

[0039] The term "haloalkynyloxy" refers to the haloalkynyl group defined above, which is bonded to the remainder of the molecule via an oxygen atom. C2-C6-haloalkynyloxy is the C2-C6-haloalkynyl group defined above, which is bonded to the remainder of the molecule via an oxygen atom. C3-C6-haloalkynyloxy is the C3-C6-haloalkynyl group defined above, which is bonded to the remainder of the molecule via an oxygen atom.

[0040] The term "cycloalkoxy" refers to a cycloalkyl group as defined above, which is bonded to the remainder of the molecule via an oxygen atom. A C3-C6 cycloalkoxy is a C3-C6 cycloalkyl group as defined above, which is bonded to the remainder of the molecule via an oxygen atom. Examples of C3-C6 cycloalkoxys include cyclopropoxy, cyclobutoxy, cyclopentoxy, and cyclohexoxy.

[0041] As used herein, the term "alkoxy-alkoxy" refers to the alkoxy group defined above, wherein one hydrogen atom is substituted with another alkoxy group defined above. As used herein, the term "C1-C3-alkoxy-C1-C3-alkoxy" refers to an alkoxy group having 1 to 3 carbon atoms as defined above, wherein one hydrogen atom is substituted with a C1-C3-alkoxy group defined above. Examples include methoxymethoxy, ethoxymethoxy, propoxymethoxy, isopropoxymethoxy, 1-methoxyethoxy, 1-ethoxyethoxy, 1-propoxyethoxy, 1-isopropoxyethoxy, 2-methoxyethoxy, 2-ethoxyethoxy, 2-propoxyethoxy, 2-isopropoxyethoxy, 1-methoxypropoxy, 1-ethoxypropoxy, 1-propoxypropoxy, 1-isopropoxypropoxy, 2-methoxypropoxy, 2-ethoxypropoxy, 2-propoxypropoxy, 2-isopropoxypropoxy, 3-methoxypropoxy, 3-ethoxypropoxy, 3-propoxypropoxy, 3-isopropoxypropoxy, etc.

[0042] As used herein, the term "alkylthio" (alkylsulfanil, "alkyl-S" or "alkyl-S(O)") k(where k is 0) represents the linear or branched saturated alkyl group defined above, which in each case typically contains 1 to 6 carbon atoms (=C1-C6-alkylthio), preferably 1 to 3 carbon atoms (=C1-C3-alkylthio), bonded via sulfur atoms at any position of the alkyl group. The C1-C2-alkylthio is methylthio or ethylthio. The C1-C3-alkylthio is further, for example, n-propylthio or 1-methylethylthio (isopropylthio). C1-C6-alkylthios are further, for example, butylthio, 1-methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio), 1,1-dimethylethylthio (tert-butylthio), pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio, or 1-ethyl-2-methylpropylthio.

[0043] As used herein, the term "haloalkylthio" refers to the alkylthio group described above in which a hydrogen atom is partially or completely substituted with fluorine, chlorine, bromine, and / or iodine. Examples of C1-C2 haloalkylthios include SCH2F, SCHF2, SCF3, SCH2Cl, SCHCl2, SCl3, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, or SC2F5. C1-C4-haloalkylthio further includes, for example, 2-fluoropropylthio, 3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2,3-dichloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, SCH2-C2F5, SCF2-C2F5, 1-(CH2F)-2-fluoroethylthio, 1-(CH2Cl)-2-chloroethylthio, 1-(CH2Br)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio, or nonafluorobutylthio. C1-C6-haloalkylthios are further, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio, or dodecafluorohexylthio.

[0044] The term "alkylsulfinyl" refers to an alkyl group as defined above, bonded via a sulfinyl[S(O)] group. For example, the term "C1-C2-alkylsulfinyl" refers to a C1-C2 alkyl group as defined above, bonded via a sulfinyl[S(O)] group. The term "C1-C3-alkylsulfinyl" refers to a C1-C3 alkyl group as defined above, bonded via a sulfinyl[S(O)] group. The term "C1-C6-alkylsulfinyl" refers to a C1-C6 alkyl group as defined above, bonded via a sulfinyl[S(O)] group. C1-C2-alkylsulfinyl is methylsulfinyl or ethylsulfinyl. C1-C3-alkylsulfinyl is further, for example, n-propylsulfinyl or 1-methylethylsulfinyl (isopropylsulfinyl). C1-C6 alkylsulfinyls include, for example, butylsulfinyl, 1-methylpropylsulfinyl (sec-butylsulfinyl), 2-methylpropylsulfinyl (isobutylsulfinyl), 1,1-dimethylethylsulfinyl (tert-butylsulfinyl), pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, and 1-methylpentylsulfinyl. These are methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl, or 1-ethyl-2-methylpropylsulfinyl.

[0045] The term "haloalkylsulfinyl" refers to the haloalkyl group defined above, which is bonded to the remainder of the molecule via a sulfinyl [S(O)] group. Examples of C1-C2 haloalkylsulfinyls include S(O)CH2F, S(O)CHF2, S(O)CF3, S(O)CH2Cl, S(O)CHCl2, S(O)CCl3, chlorofluoromethylsulfinyl, dichlorofluoromethylsulfinyl, chlorodifluoromethylsulfinyl, 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl, or S(O)C2F5. C1-C3-haloalkylsulfinyls are further, for example, 2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl, 2,3-dichloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl, 3,3,3-trifluoropropylsulfinyl, 3,3,3-trichloropropylsulfinyl, S(O)CH2-C2F5, S(O)CF2-C2F5, 1-(CH2F)-2-fluoroethylsulfinyl, 1-(CH2Cl)-2-chloroethylsulfinyl, or 1-(CH2Br)-2-bromoethylsulfinyl. C1-C4-haloalkylsulfinyls are further, for example, 4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl, or nonafluorobutylsulfinyl.C1-C6-haloalkylsulfinyls are further, for example, 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-bromopentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl, or dodecafluorohexylsulfinyl.

[0046] The term "alkylsulfonyl" refers to an alkyl group as defined above, bonded via a sulfonyl[S(O)2] group. The term "C1-C2-alkylsulfonyl" refers to a C1-C2 alkyl group as defined above, bonded via a sulfonyl[S(O)2] group. The term "C1-C3-alkylsulfonyl" refers to a C1-C3 alkyl group as defined above, bonded via a sulfonyl[S(O)2] group. The term "C1-C6-alkylsulfonyl" refers to a C1-C6 alkyl group as defined above, bonded via a sulfonyl[S(O)2] group. C1-C2-alkylsulfonyl is methylsulfonyl or ethylsulfonyl. C1-C3-alkylsulfonyl is further, for example, n-propylsulfonyl or 1-methylethylsulfonyl (isopropylsulfonyl). C1-C6 alkylsulfonyls include, for example, butylsulfonyl, 1-methylpropylsulfonyl (sec-butylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl), 1,1-dimethylethylsulfonyl (tert-butylsulfonyl), pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, and 1-methylpentylsulfonyl. These are 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl, or 1-ethyl-2-methylpropylsulfonyl.

[0047] The term "haloalkylsulfonyl" refers to the haloalkyl group defined above, which is bonded to the remainder of the molecule via a sulfonyl [S(O)2] group. Examples of C1-C2 haloalkylsulfonyls include S(O)2CH2F, S(O)2CHF2, S(O)2CF3, S(O)2CH2Cl, S(O)2CHCl2, S(O)2CCl3, chlorofluoromethylsulfonyl, dichlorofluoromethylsulfonyl, chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, or S(O)2C2F5. C1-C3-haloalkylsulfonyls are further, for example, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2,3-dichloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, S(O)2CH2-C2F5, S(O)2CF2-C2F5, 1-(CH2F)-2-fluoroethylsulfonyl, 1-(CH2Cl)-2-chloroethylsulfonyl, or 1-(CH2Br)-2-bromoethylsulfonyl. C1-C4-haloalkylsulfonyls are further, for example, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl, or nonafluorobutylsulfonyl.C1-C6-haloalkylsulfonyls are further, for example, 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonyl, 5-iodopentylsulfonyl, undecafluoropentylsulfonyl, 6-fluorohexylsulfonyl, 6-chlorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl, or dodecafluorohexylsulfonyl.

[0048] The substituent "oxo" replaces a CH2 group with a C(=O) group.

[0049] The suffix "-carbonyl" in a group means that, in each case, this group is bonded to the rest of the molecule via a carbonyl C=O group. This is the case, for example, in alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, and arylcarbonyl groups.

[0050] The term "alkoxycarbonyl" refers to the alkoxy group defined above, which is bonded to the remainder of the molecule via a carbonyl[C(=O)] group. C1-C3 alkoxycarbonyls are the C1-C3 alkoxy groups defined above, which are bonded to the remainder of the molecule via a carbonyl[C(=O)] group. Examples of C1-C3 alkoxycarbonyls are methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, and isopropoxycarbonyl. C1-C6 alkoxycarbonyls refer to the C1-C6 alkoxy groups defined above, which are bonded to the remainder of the molecule via a carbonyl[C(=O)] group. Examples of C1-C6 alkoxycarbonyls include those listed for C1-C3 alkoxycarbonyls, as well as n-butoxycarbonyl, sec-butoxycarbonyl, isobutoxycarbonyl, tert-butoxycarbonyl, pentoxycarbonyl, and hexoxycarbonyl.

[0051] The term "haloalkoxycarbonyl" refers to a haloalkyl group, as defined above, that is bonded to the remainder of the molecule via a carbonyl[C(=O)] group. A C1-C3 haloalkoxycarbonyl is a C1-C3 alkoxy group, as defined above, that is bonded to the remainder of the molecule via a carbonyl[C(=O)] group. Examples of C1-C3 haloalkoxycarbonyls include -C(O)OCH2F, -C(O)OCHF2, -C(O)OCF3, -C(O)OCH2Cl, -C(O)OCHCl2, -C(O)OCCl3, chlorofluoromethoxycarbonyl, dichlorofluoromethoxycarbonyl, chlorodifluoromethoxycarbonyl, 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2-iodoethoxycarbonyl, 2,2-difluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2-chloro-2-fluoroethoxycarbonyl, 2-chloro-2,2-difluoroethoxycarbonyl, 2,2-dichloro-2-fluoroethoxycarbonyl, and 2,2,2-trichloroethoxy These are cyclocarbonyl, -C(O)OC2F5, 2-fluoropropoxycarbonyl, 3-fluoropropoxycarbonyl, 2,2-difluoropropoxycarbonyl, 2,3-difluoropropoxycarbonyl, 2-chloropropoxycarbonyl, 3-chloropropoxycarbonyl, 2,3-dichloropropoxycarbonyl, 2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl, 3,3,3-trichloropropoxycarbonyl, -C(O)OCH2-C2F5, -C(O)OCF2-C2F5, 1-(CH2F)-2-fluoroethoxycarbonyl, 1-(CH2Cl)-2-chloroethoxycarbonyl, or 1-(CH2Br)-2-bromoethoxycarbonyl.

[0052] The term "alkoxycarbonyl-alkyl" refers to an alkyl group as defined above, in which one hydrogen atom is substituted with the alkoxycarbonyl group defined above. C1~C6-alkoxycarbonyl-C1~C6-alkyl is a C1~C6-alkyl group as defined above, in which one hydrogen atom is substituted with the C1~C6-alkoxycarbonyl group defined above.

[0053] Phenyl-(C1-C2)-alkyl is a C1-C2 alkyl group as defined above, in which one hydrogen atom is substituted by a phenyl ring (i.e., the bond to the rest of the molecule is via an alkyl group). Examples include benzyl, 1-phenylethyl, and 2-phenylethyl. Phenyl-(C1-C3)-alkyl is a C1-C3 alkyl group as defined above, in which one hydrogen atom is substituted by a phenyl ring (i.e., the bond to the rest of the molecule is via an alkyl group). Examples include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, or 2-phenyl-2-propyl.

[0054] A furanyl-(C1-C3)-alkyl group is a C1-C3 alkyl group as defined above, in which one hydrogen atom is substituted by a 2- or 3-furanyl ring (i.e., the bond to the rest of the molecule is via an alkyl group). Examples include furan-2-yl-methyl, furan-3-yl-methyl, 1-(furan-2-yl)-ethyl, 1-(furan-3-yl)-ethyl, 2-(furan-2-yl)-ethyl, and 2-(furan-3-yl)-ethyl.

[0055] Phenylthio is a phenyl ring that is bonded to the rest of the molecule via a sulfur atom.

[0056] Phenylsulfinyl is a phenyl ring that is bonded to the rest of the molecule via an S(O) group.

[0057] Phenylsulfonyl is a phenyl ring that is attached to the rest of the molecule via two S(O) groups.

[0058] As used herein, the term “aryl” refers to a polyunsaturated aromatic hydrocarbyl group having a monocyclic ring (i.e., phenyl) or multiple aromatic rings (e.g., naphthyl) fused together, typically containing 5 to 12 atoms; preferably 6 to 10 atoms, where at least one ring is aromatic. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, and anthracyl. The preferred aryl group according to the present invention is phenyl.

[0059] As used herein, the term "arylalkyl" refers to an alkyl-aryl group, where alkyl and aryl are as defined herein.

[0060] Examples of arylalkyl groups include, but are not limited to, benzyl.

[0061] As used herein, the term “aryloxycarbonyl” refers to a -C(O)-O-aryl group, where aryl is as defined herein. A non-limiting example of an aryloxycarbonyl is phenyloxycarbonyl.

[0062] An unsaturated carbon ring contains at least one CC double bond.

[0063] An unsaturated heterocycle contains at least one CC and / or CN and / or NN double bond.

[0064] A partially unsaturated carbon ring contains fewer than the maximum number of CC double bonds allowed by the ring size.

[0065] A partially unsaturated carbon ring contains fewer than the maximum number of CC and / or CN and / or NN double bonds allowed by the ring size.

[0066] Examples of 3-membered, 4-membered, 5-membered, or 6-membered saturated, partially unsaturated, fully unsaturated, or aromatic carbocyclic compounds include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloprop-1-enyl, cycloprop-2-enyl, cyclobuto-1-enyl, cyclobuto-2-enyl, cyclobutadienyl, cyclopento-1-enyl, cyclopento-2-enyl, cyclopento-3-enyl, and cyclopento. Examples include cyclopenta-1,3-dienyl, cyclopenta-1,4-dienyl, cyclopenta-2,4-dienyl, cyclohexe-1-enyl, cyclohexe-2-enyl, cyclohexe-3-enyl, cyclohexa-1,3-dienyl, cyclohexa-1,4-dienyl, cyclohexa-1,5-dienyl, cyclohexa-2,4-dienyl, cyclohexa-2,5-dienyl, and phenol.

[0067] Examples of saturated, partially unsaturated, fully unsaturated, or aromatic heterocycles with 3, 4, 5, 6, or 7 members are as follows:

[0068] 3-membered, 4-membered, 5-membered, or 6-membered monocyclic saturated heterocycles: for example, oxiran-2-yl, thiran-2-yl, aziridin-1-yl, aziridin-2-yl, oxetan-2-yl, oxetan-3-yl, thietan-2-yl, thietan-3-yl, 1-oxothietan-2-yl, 1-oxothietan-3-yl, 1,1-dioxothietan-2-yl, 1,1-dioxothietan-3-yl, azetidine-1-yl, azetidine-2-yl, azetidine-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothietan -2-yl, tetrahydrothien-3-yl, 1-oxotetrahydrothien-2-yl, 1,1-dioxotetrahydrothien-2-yl, 1-oxotetrahydrothien-3-yl, 1,1-dioxotetrahydrothien-3-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-ditholan-2-yl, 1,3-ditholan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, pyrrolidine-1-yl, pyrrolin-1-yl, pyrrolin-1-yl Roridine-2-yl, pyrrolidine-3-yl, pyrazolidine-1-yl, pyrazolidine-3-yl, pyrazolidine-4-yl, pyrazolidine-5-yl, imidazolidine-1-yl, imidazolidine-2-yl, imidazolidine-4-yl, oxazolidine-2-yl, oxazolidine-3-yl, oxazolidine-4-yl, oxazolidine-5-yl, isoxazolidine-2-yl, isoxazolidine-3-yl, isoxazolidine-4-yl, isoxazolidine-5-yl, thiazolidine-2-yl, thiazolidine-3-yl, thiazolidine-4- Il, thiazolidined-5-yl, isothiazolidined-2-yl, isothiazolidined-3-yl, isothiazolidined-4-yl, isothiazolidined-5-yl, 1,2,4-oxadiazolidined-3-yl, 1,2,4-oxadiazolidined-5-yl, 1,2,4-thiadiazolidined-3-yl, 1,2,4-thiadiazolidined-5-yl, 1,3,4-oxadiazolidined-2-yl, 1,3,4-thiadiazolidined-2-yl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 1,3-dioxane-2-yl, 1,3-Dioxan-4-yl, 1,3-Dioxan-5-yl, 1,4-Dioxan-2-yl, Piperidine-1-yl, Piperidine-2-yl, Piperidine-3-yl, Piperidine-4-yl, Hexahydropyridazine-1-yl, Hexahydropyridazine-3-yl, Hexahydropyridazine-4-yl, Hexahydropyrimidine-1-yl, Hexahydropyrimidine-2-yl, Hexahydropyrimidine-4-yl, Hexahydropyrimidine-5-yl, Piperazine-1-yl, Piperazine-2-yl, Morpholin-2-yl, Morpholin-3-yl, Morpholin-4-yl, Thiomorpholin-2-yl, Thiomorpholin-3-yl, Thiomorpholin-4-yl, 1-Oxothiomorpholin-2-yl, 1 Oxothiomorpholin-3-yl, 1-oxothiomorpholin-4-yl, 1,1-dioxothiomorpholin-2-yl, 1,1-dioxothiomorpholin-3-yl, 1,1-dioxothiomorpholin-4-yl, etc.

[0069] Five-membered or six-membered monocyclic partial unsaturated heterocycles: for example, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 2-pyrroline-2-yl, 2-pyrroline-3-yl, 3-pyrroline-2-yl, 3-pyrroline-3-yl, 2-isoxazoline-3-yl, 3-isoxazoline-3-yl, 4-isoxazoline-3- Il, 2-Isoxazolin-4-yl, 3-Isoxazolin-4-yl, 4-Isoxazolin-4-yl, 2-Isoxazolin-5-yl, 3-Isoxazolin-5-yl, 4-Isoxazolin-5-yl, 2-Isothiazolin-3-yl, 3-Isothiazolin-3-yl, 4-Isothiazolin-3-yl, 2-Isothiazolin-4-yl, 3-Isothiazolin-4-yl, 4-Isothiazolin-4-yl, 2-Isothiazolin-5-yl, 3-Isothiazolin-5-yl, 4-Isothiazolin-5-yl, 2,3-Dihydropyrazole-1-yl, 2,3 -dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl , 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,6-dihydro-2H-pyran-2-,-3-,-4-,-5- or 6-yl, 3,4-dihydro-2H-pyran-2-,-3-,-4-,-5- or 6-yl, 3,6-dihydro-2H-thiopyran-2-,-3-,-4-,-5- or 6-yl, 3,4-dihydro-2H-thiopyran-2-,-3-,-4-,-5- or 6-yl, 2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4-di- or tetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrimidinyl, di- or tetrahydropyridinyl;

[0070] Two groups bonded to the same nitrogen atom (for example, R b and R h , R b2 and R b3 If these, together with the nitrogen atoms to which they are bonded, form a 3-membered, 4-membered, 5-membered, 6-membered, or 7-membered saturated N-bonded heterocycle that may contain further heteroatoms or heteroatomic groups selected from the group consisting of N, O, S, S(O) and S(O)2 as ring members, then, for example, this is aziridin-1-yl, azetidine-1-yl, pyrrolidine-1-yl, pyrazolidine-1-yl, imidazolidine-1-yl, oxazolidine-3-yl, thiazolidin-3-yl, isoxazolidine-2-yl, isothiazolin-2-yl, piperazine-1-yl, piperazine-1-yl, morpholine-1-yl, thiomorpholine-1-yl, 1-oxothiomorpholine-1-yl, 1,1-dioxothiomorpholine-1-yl, azepan-1-yl, or 1,4-diazepan-1-yl.

[0071] The following descriptions relating to preferred embodiments of the modification (substituent) of the compound of formula I are effective on their own, and are also preferably effective in combination with each other, and in combination with their stereoisomers, tautomers, or salts.

[0072] The following description relating to preferred embodiments of the variable elements is, where applicable, effective on its own and preferably in combination with respect to compounds of Formula I, and with respect to the uses and methods and compositions according to the present invention.

[0073] Formula (I) [wherein, R 7 is methyl or ethyl, and the other variable elements are as defined herein] compounds can be in the S configuration or the R configuration at the carbon with the R 7 / R 9 substitution having a stereocenter (#). In the context of the present invention, compounds of formula (I) [wherein, R 7 is methyl or ethyl, and the other variable elements are as defined herein] are preferably compounds having the R configuration at the stereocenter, i.e., compounds of formula (I.R).

Chemical Formula

[0074] Preferably, R 1 is hydrogen or (C1-C3)-alkyl, more preferably hydrogen.

[0075] Preferably, R 8 is hydrogen or (C1-C3)-alkyl, more preferably hydrogen.

[0076] Preferably, both R 1 and R 8 are hydrogen.

[0077] Preferably, R 2 is hydrogen, halogen or (C1-C3)-alkyl. More preferably, R 2 is hydrogen or halogen, for example, H, F, or Cl. In particular, R 2 is hydrogen.

[0078] Preferably, R 6 is hydrogen, halogen or (C1-C3)-alkyl. More preferably, R 6 is hydrogen.

[0079] Preferably, both R 2 and R 6 are, independently of each other, hydrogen, halogen or (C1-C3)-alkyl. More preferably, R 2is hydrogen or a halogen, for example, H, F, or Cl, and R 6 It is hydrogen. In particular, R 2 is hydrogen, R 6 It is hydrogen.

[0080] Preferably, R 3 is hydrogen, halogen, (C1~C3)-alkyl, (C1~C3)-haloalkyl, (C1~C3)-alkoxy, or (C1~C3)-haloalkoxy. More preferably, R 3 is hydrogen, halogen, (C1~C2)-alkyl, (C1~C2)-haloalkyl, (C1~C2)-alkoxy, or (C1~C2)-haloalkoxy. Most preferably, R 3 This is hydrogen or a halogen, particularly H, F, Cl, or Br.

[0081] Preferably, R 5 is hydrogen, halogen, (C1~C3)-alkyl, (C1~C3)-haloalkyl, (C1~C3)-alkoxy, or (C1~C3)-haloalkoxy. More preferably, R 5 is hydrogen, halogen, or (C1-C2) alkoxy. Most preferably, R 5 This is hydrogen or a halogen, particularly H, F, Cl, or Br.

[0082] Preferably, R 3 and R 5 R is independently of each other: hydrogen, halogen, (C1~C3)-alkyl, (C1~C3)-haloalkyl, (C1~C3)-alkoxy, or (C1~C3)-haloalkoxy. More preferably, 3 is hydrogen, halogen, (C1~C3)-alkyl, (C1~C3)-haloalkyl, (C1~C3)-alkoxy, or (C1~C3)-haloalkoxy, and R 5 is hydrogen, halogen, or (C1-C2)-alkoxy. In particular, R 3 and R 5 These are, independently of each other, hydrogen or halogen. More specifically, R 3 is a halogen, and R 5is hydrogen or a halogen.

[0083] In another preferred embodiment, R 3 is hydrogen, a halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, or (C1-C3)-haloalkoxy, and R 5 is hydrogen or a halogen. More preferably, R 3 is hydrogen, a halogen, (C1-C2)-alkyl, (C1-C2)-haloalkyl, (C1-C2)-alkoxy, or (C1-C2)-haloalkoxy, and R 5 is hydrogen or a halogen.

[0084] Preferably, R 4 is hydrogen or a halogen. In particular, R 4 is hydrogen.

[0085] R 7 is methyl or ethyl, preferably methyl.

[0086] Preferably, X is oxygen.

[0087] Preferably, R 10 is methyl or ethyl. In particular, R 10 is methyl.

[0088] Embodiment Q.1: Preferably, Q is of the formula (Z-Y)

Chemical formula

[0089] In another embodiment, the present invention relates to a compound in which Q is as defined in embodiment Q.1, wherein R 10 is methyl; R 11 , R 12 , R 13 , R 14 is hydrogen; or R 10 and R 14 together with the carbon atom to which they are attached form a 4- to 6-membered saturated or partially unsaturated carbocyclic ring or a 5-membered partially unsaturated heterocyclic ring containing one oxygen, nitrogen or sulfur atom as a ring member.

[0090] Embodiment Q.2: More preferably, Q is of the formula (Z-Y)

Chemical formula

[0091] In another embodiment, the present invention relates to a compound as defined in Embodiment Q.2, wherein Q is a compound as defined in the formula, R 10 It is methyl; R 11 , R 12 , R 13 , R 14 is hydrogen; or R 10 and R 14 These, together with the carbon atoms to which they are bonded, form a 4- to 6-membered saturated or partially unsaturated carbon ring or a 5-membered partially unsaturated heterocycle containing one oxygen atom as a ring member;

[0092] Embodiment Q.3: Most preferably, Q is formula ZY [ka] [In the formula, arrows represent bonds to adjacent nitrogen atoms, and substituents have the following meanings] R 10 It is methyl; R 11 , R 12, R 13 , R 14 is hydrogen; or R 10 and R 14 These, together with the carbon atoms to which they are bonded, form a 4- to 6-membered saturated or partially unsaturated carbon ring or a 5-membered saturated or partially unsaturated heterocycle containing one oxygen atom as a ring member; Y is CO2R e CONR b R h , or CONR e SO2R a and; R a is (C1~C6)-alkyl or (C1~C6)-haloalkyl; R b is hydrogen; Each R e These are independently hydrogen, or (C1-C6)-alkyl, or (C3-C6)-cycloalkyl, where each of the last two groups is substituted with m groups selected from the group consisting of (C1-C2)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; R h is hydrogen, or (C1~C6)-alkyl, (C1~C2)-alkoxy, (C3~C6)-cycloalkyl, (C2~C4)-alkenyl, (C1~C6)-alkoxycarbonyl-(C1~C6)-alkyl, or (C3~C4)-alkynyl, where each of the last six groups is substituted with m groups selected from the group consisting of (C1~C2)-alkyl, (C1~C2)-alkoxy, and (C1~C2)-alkoxy-(C1~C2)-alkoxy; or R b and R h Together with the nitrogen atoms to which they are bonded, they form a saturated six-membered N-bonded heterocycle that may contain one oxygen atom as a ring member; m is 0, 1, or 2, independently of each occurrence; n is 1. It represents the basis of.

[0093] In another embodiment, the present invention relates to a compound as defined in Embodiment Q.3, wherein Q is a compound as defined in the formula, R 10 It is methyl; R 11 , R 12 , R 13 , R 14 is hydrogen; or R 10 and R 14 These, together with the carbon atoms to which they are bonded, form a 4- to 6-membered saturated or partially unsaturated carbon ring or a 5-membered partially unsaturated heterocycle containing one oxygen atom as a ring member;

[0094] Formula ZY [ka] [In the formula, arrows represent bonds to adjacent nitrogen atoms, and substituents have the following meanings] R 10 It is methyl; R 11 , R 12 , R 13 , R 14 is hydrogen; n is either 1 or 2. A typical example of Q representing the basis of is the following Z 1 -Y and Z 2 -Y-based: [ka]

[0095] A preferred example of Q is Z 1 -Y and Z 2 -Y group, in the formula, Y is CO2R e And, R e These are hydrogen, (C1-C6)-alkyl, or (C3-C6)-cycloalkyl.

[0096] Formula ZY [ka] [In the formula, arrows represent bonds to adjacent nitrogen atoms, and substituents have the following meanings] R 11 , R 12 , R 13 is hydrogen; R 10 and R 14 These, together with the carbon atoms to which they are bonded, form a 4- to 6-membered saturated or partially unsaturated carbon ring or a 5-membered saturated heterocycle containing one oxygen atom as a ring member; n is 1. Further representative examples of Q representing the basis of are the following Z 3 -Y~Z 8 -Y-based: [ka]

[0097] A preferred example of Q is Z 3 -Y~Z 8 -Y group, in formula Y is CO2R e CONR b R h , or CONR e SO2R a and; R a is (C1~C6)-alkyl or (C1~C6)-haloalkyl; R b is hydrogen; Each R e These are independently hydrogen, or (C1-C6)-alkyl or (C3-C6)-cycloalkyl, where each of the last two groups is substituted with m groups selected from the group consisting of (C1-C2)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; R his hydrogen, or (C1~C6)-alkyl, (C1~C2)-alkoxy, (C3~C6)-cycloalkyl, (C2~C4)-alkenyl, (C1~C6)-alkoxycarbonyl-(C1~C6)-alkyl, or (C3~C4)-alkynyl, where each of the last six groups is substituted with m groups selected from the group consisting of (C1~C2)-alkyl, (C1~C2)-alkoxy, and (C1~C2)-alkoxy-(C1~C2)-alkoxy; or R b and R h Together with the nitrogen atoms to which they are bonded, they form a saturated six-membered N-bonded heterocycle that may contain one oxygen atom as a ring member; m is 0, 1, or 2; n is 1.

[0098] Embodiment E.1: In a particular embodiment, the substituents in the compound of formula (I) have the following meanings: R 1 is hydrogen or (C1~C3)-alkyl; R 2 is hydrogen, halogen, or (C1-C3) alkyl; R 3 is hydrogen, halogen, (C1~C3)-alkyl, (C1~C3)-haloalkyl, (C1~C3)-alkoxy, or (C1~C3)-haloalkoxy; R 4 is hydrogen or halogen; R 5 is hydrogen, halogen, (C1~C3)-alkyl, (C1~C3)-haloalkyl, (C1~C3)-alkoxy, or (C1~C3)-haloalkoxy; R 6 is hydrogen, halogen, or (C1-C3) alkyl; R 7 is either methyl or ethyl; R 8 is hydrogen or (C1~C3)-alkyl; R 9 is hydrogen; X is oxygen. Q is given by equation (ZY) [ka] [In the formula, arrows represent bonds to adjacent nitrogen atoms, and substituents have the following meanings] R 10 It is methyl; R 11 , R 12 , R 13 , R 14 is hydrogen; or R 10 and R 14 These, together with the carbon atoms to which they are bonded, form a 4- to 6-membered saturated or partially unsaturated carbon ring or a 5-membered saturated or partially unsaturated heterocycle containing one oxygen atom as a ring member; Y is CO2R e CONR b R h , or CONR e SO2R a and; R a is (C1~C6)-alkyl or (C1~C6)-haloalkyl; R b is hydrogen; Each R e These are independently hydrogen, or (C1-C6)-alkyl, or (C3-C6)-cycloalkyl, where each of the last two groups is fluorine, chlorine, bromine, cyano, or CO2R. a It is substituted with m groups selected from the group consisting of (C1~C2)-alkoxy, (C1~C2)-haloalkoxy, (C1~C3)-alkylthio, (C1~C3)-haloalkylthio, (C1~C3)-alkylsulfinyl, (C1~C3)-haloalkylsulfinyl, (C1~C3)-alkylsulfonyl, (C1~C3)-haloalkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; R hThese are hydrogen, or (C1~C6)-alkyl, (C1~C2)-alkoxy, (C3~C6)-cycloalkyl, (C2~C4)-alkenyl, (C1~C6)-alkoxycarbonyl-(C1~C6)-alkyl, or (C3~C4)-alkynyl, where each of the last six groups is fluorine, chlorine, bromine, cyano, CO2R a , substituted with m groups selected from the group consisting of (C1~C2)-alkyl, (C1~C2)-alkoxy, and (C1~C2)-alkoxy-(C1~C2)-alkoxy; or R b and R h Together with the nitrogen atoms to which they are bonded, they form a saturated six-membered N-bonded heterocycle that may contain one oxygen atom as a ring member; m is 0, 1, or 2, independently of each occurrence; n is 1. It represents the basis of.

[0099] In another embodiment, the present invention relates to a compound as defined in Embodiment E.1, wherein, R 10 It is methyl; R 11 , R 12 , R 13 , R 14 is hydrogen; or R 10 and R 14 These, together with the carbon atoms to which they are bonded, form a 4- to 6-membered saturated or partially unsaturated carbon ring or a 5-membered partially unsaturated heterocycle containing one oxygen atom as a ring member;

[0100] Embodiment E.2: In another specific embodiment, in the compound of formula (I), the substituents have the following meanings: R 1 is hydrogen or (C1~C3)-alkyl; R 2 is hydrogen, halogen, or (C1-C3) alkyl; R 3is hydrogen, halogen, (C1~C3)-alkyl, (C1~C3)-haloalkyl, (C1~C3)-alkoxy, or (C1~C3)-haloalkoxy; R 4 is hydrogen or halogen; R 5 is hydrogen, halogen, (C1~C3)-alkyl, (C1~C3)-haloalkyl, (C1~C3)-alkoxy, or (C1~C3)-haloalkoxy; R 6 is hydrogen, halogen, or (C1-C3) alkyl; R 7 is either methyl or ethyl; R 8 is hydrogen or (C1~C3)-alkyl; R 9 is hydrogen; X is oxygen; Q is given by equation (ZY) [ka] [In the formula, arrows represent bonds to adjacent nitrogen atoms, and substituents have the following meanings] R 10 It is methyl; R 11 , R 12 , R 13 , R 14 is hydrogen; or R 10 and R 14 These, together with the carbon atoms to which they are bonded, form a 4- to 6-membered saturated or partially unsaturated carbon ring or a 5-membered saturated or partially unsaturated heterocycle containing one oxygen atom as a ring member; Y is CO2R e CONR b R h , or CONR e SO2R a and; R aThese are (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C3-C4)-alkynyl, or (C3-C6)-cycloalkyl, each of which is substituted with m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy, and (C1-C3)-alkoxy; R b is hydrogen; Each R e These are independently hydrogen, or (C1-C6)-alkyl or (C3-C6)-cycloalkyl, where each of the last two groups is substituted with m groups selected from the group consisting of (C1-C2)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; R h is hydrogen, or (C1~C6)-alkyl, (C1~C2)-alkoxy, (C3~C6)-cycloalkyl, (C2~C4)-alkenyl, (C1~C6)-alkoxycarbonyl-(C1~C6)-alkyl, or (C3~C4)-alkynyl, where each of the last six groups is substituted with m groups selected from the group consisting of (C1~C2)-alkyl, (C1~C2)-alkoxy, and (C1~C2)-alkoxy-(C1~C2)-alkoxy; or R b and R h Together with the nitrogen atoms to which they are bonded, they form a saturated six-membered N-bonded heterocycle that may contain one oxygen atom as a ring member; m is 0, 1, or 2, independently of each occurrence; n is 1. It represents the basis of.

[0101] In another embodiment, the present invention relates to a compound as defined in Embodiment E.2, wherein, R 10 It is methyl; R 11 , R 12 , R 13 , R 14is hydrogen; or R 10 and R 14 These, together with the carbon atoms to which they are bonded, form a 4- to 6-membered saturated or partially unsaturated carbon ring or a 5-membered partially unsaturated heterocycle containing one oxygen atom as a ring member;

[0102] Embodiment E.3: In a further specific embodiment, in the compound of formula (I), the substituents have the following meanings: R 1 is hydrogen; R 2 is hydrogen or halogen; R 3 It is a halogen; R 4 is hydrogen or halogen; R 5 is hydrogen or halogen; R 6 is hydrogen; R 7 is either methyl or ethyl; R 8 is hydrogen; R 9 is hydrogen; X is oxygen; Q is given by equation (ZY) [ka] [In the formula, arrows represent bonds to adjacent nitrogen atoms, and substituents have the following meanings] R 10 It is methyl; R 11 , R 12 , R 13 , R 14 is hydrogen; or R 10 and R 14 These, together with the carbon atoms to which they are bonded, form a 4- to 6-membered saturated or partially unsaturated carbon ring or a 5-membered saturated or partially unsaturated heterocycle containing one oxygen atom as a ring member; Y is CO2R e CONRb R h , or CONR e SO2R a and; R a is (C1~C6)-alkyl or (C1~C6)-haloalkyl; R b is hydrogen; Each R e These are independently hydrogen, or (C1-C6)-alkyl, or (C3-C6)-cycloalkyl, where each of the last two groups is fluorine, chlorine, bromine, cyano, or CO2R. a It is substituted with m groups selected from the group consisting of (C1~C2)-alkoxy, (C1~C2)-haloalkoxy, (C1~C3)-alkylthio, (C1~C3)-haloalkylthio, (C1~C3)-alkylsulfinyl, (C1~C3)-haloalkylsulfinyl, (C1~C3)-alkylsulfonyl, (C1~C3)-haloalkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; R h These are hydrogen, or (C1~C6)-alkyl, (C1~C2)-alkoxy, (C3~C6)-cycloalkyl, (C2~C4)-alkenyl, (C1~C6)-alkoxycarbonyl-(C1~C6)-alkyl, or (C3~C4)-alkynyl, where each of the last six groups is fluorine, chlorine, bromine, cyano, CO2R a , substituted with m groups selected from the group consisting of (C1~C2)-alkyl, (C1~C2)-alkoxy, and (C1~C2)-alkoxy-(C1~C2)-alkoxy; or R b and R h Together with the nitrogen atoms to which they are bonded, they form a saturated six-membered N-bonded heterocycle that may contain one oxygen atom as a ring member; m is 0, 1, or 2, independently of each occurrence; n is 1. It represents the basis of.

[0103] In another embodiment, the present invention relates to a compound as defined in Embodiment E.3, wherein, R 10 It is methyl; R 11 , R 12 , R 13 , R 14 is hydrogen; or R 10 and R 14 These, together with the carbon atoms to which they are bonded, form a 4- to 6-membered saturated or partially unsaturated carbon ring or a 5-membered partially unsaturated heterocycle containing one oxygen atom as a ring member;

[0104] Embodiment E.4: In a further specific embodiment, in the compound of formula (I), the substituents have the following meanings: R 1 is hydrogen; R 2 is hydrogen or halogen; R 3 It is a halogen; R 4 is hydrogen or halogen; R 5 is hydrogen or halogen; R 6 is hydrogen; R 7 is either methyl or ethyl; R 8 is hydrogen; R 9 is hydrogen; X is oxygen; Q is given by equation (ZY) [ka] [In the formula, arrows represent bonds to adjacent nitrogen atoms, and substituents have the following meanings] R 10 It is methyl; R 11 , R 12 , R 13 , R 14 is hydrogen; or R10 and R 14 These, together with the carbon atoms to which they are bonded, form a 4- to 6-membered saturated or partially unsaturated carbon ring or a 5-membered saturated or partially unsaturated heterocycle containing one oxygen atom as a ring member; Y is CO2R e CONR b R h , or CONR e SO2R a and; R a These are (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C3-C4)-alkynyl, or (C3-C6)-cycloalkyl, each of which is substituted with m groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy, and (C1-C3)-alkoxy; R b is hydrogen; Each R e These are independently hydrogen, or (C1-C6)-alkyl, or (C3-C6)-cycloalkyl, where each of the last two groups is substituted with m groups selected from the group consisting of (C1-C2)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; R h is hydrogen, or (C1~C6)-alkyl, (C1~C2)-alkoxy, (C3~C6)-cycloalkyl, (C2~C4)-alkenyl, (C1~C6)-alkoxycarbonyl-(C1~C6)-alkyl, or (C3~C4)-alkynyl, where each of the last six groups is substituted with m groups selected from the group consisting of (C1~C2)-alkyl, (C1~C2)-alkoxy, and (C1~C2)-alkoxy-(C1~C2)-alkoxy; or R b and R h Together with the nitrogen atoms to which they are bonded, they form a saturated six-membered N-bonded heterocycle that may contain one oxygen atom as a ring member; m is 0, 1, or 2, independently of each occurrence; n is 1. It represents the basis of.

[0105] In another embodiment, the present invention relates to a compound as defined in Embodiment E.4, wherein, R 10 It is methyl; R 11 , R 12 , R 13 , R 14 is hydrogen; or R 10 and R 14 These, together with the carbon atoms to which they are bonded, form a 4- to 6-membered saturated or partially unsaturated carbon ring or a 5-membered partially unsaturated heterocycle containing one oxygen atom as a ring member;

[0106] Embodiment E.5: In a further specific embodiment, in the compound of formula (I), the substituents have the following meanings: R 1 is hydrogen; R 2 is hydrogen or halogen; R 3 It is a halogen; R 4 is hydrogen or halogen; R 5 is hydrogen or halogen; R 6 is hydrogen; R 7 is either methyl or ethyl; R 8 is hydrogen; R 9 is hydrogen; X is oxygen; Q is given by equation (ZY) [ka] [In the formula, arrows represent bonds to adjacent nitrogen atoms, and substituents have the following meanings] R 10 It is methyl; R 11 , R 12 , R 13 , R 14 is hydrogen; or R 10 and R 14 These, together with the carbon atoms to which they are bonded, form a 4- to 6-membered saturated or partially unsaturated carbon ring or a 5-membered saturated or partially unsaturated heterocycle containing one oxygen atom as a ring member; Y is CO2R e And, R e is hydrogen, or (C1~C6)-alkyl or (C3~C6)-cycloalkyl, where each of the last two groups is substituted with m groups selected from the group consisting of (C1~C2)-alkoxy, (C1~C3)-alkylthio, (C1~C3)-alkylsulfinyl, (C1~C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; m is 0, 1, or 2, independently of each occurrence; n is 1. It represents the basis of.

[0107] In another embodiment, the present invention relates to a compound as defined in Embodiment E.5, wherein, R 10 It is methyl; R 11 , R 12 , R 13 , R 14 is hydrogen; or R 10 and R 14 These, together with the carbon atoms to which they are bonded, form a 4- to 6-membered saturated or partially unsaturated carbon ring or a 5-membered partially unsaturated heterocycle containing one oxygen atom as a ring member;

[0108] Embodiment E.6: In a further specific embodiment, in the compound of formula (IR), the substituents have the following meanings: R 1 is hydrogen; R 2is hydrogen or halogen; R 3 It is a halogen; R 4 is hydrogen or halogen; R 5 is hydrogen or halogen; R 6 is hydrogen; R 7 is either methyl or ethyl; R 8 is hydrogen; R 9 is hydrogen; X is oxygen; Q is given by equation (ZY) [ka] [In the formula, arrows represent bonds to adjacent nitrogen atoms, and substituents have the following meanings] R 10 It is methyl; R 11 , R 12 , R 13 , R 14 is hydrogen; or R 10 and R 14 These, together with the carbon atoms to which they are bonded, form a 4- to 6-membered saturated or partially unsaturated carbon ring or a 5-membered saturated or partially unsaturated heterocycle containing one oxygen atom as a ring member; Y is CO2R e And, R e is hydrogen, or (C1~C6)-alkyl or (C3~C6)-cycloalkyl, where each of the last two groups is substituted with m groups selected from the group consisting of (C1~C2)-alkoxy, (C1~C3)-alkylthio, (C1~C3)-alkylsulfinyl, (C1~C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; m is 0, 1, or 2; n is 1. It represents the basis of.

[0109] In another embodiment, the present invention relates to a compound as defined in Embodiment E.6, wherein, R 10 It is methyl; R 11 , R 12 , R 13 , R 14 is hydrogen; or R 10 and R 14 These, together with the carbon atoms to which they are bonded, form a 4- to 6-membered saturated or partially unsaturated carbon ring or a 5-membered partially unsaturated heterocycle containing one oxygen atom as a ring member;

[0110] In the context of the present invention, R 1 , R 2 , R 6 , R 8 , and R 9 is hydrogen, R 7 X is methyl, X is oxygen, and Q is Z 1 -Y~Z 8 -Y is either and R 3 , R 4 , R 5 Compounds of formula (I) in which Q has the meanings defined in rows 1 to 1944 of Table 1 below are particularly preferred. [ka]

[0111] [Table 1]

[0112] [Table 2]

[0113] [Table 3]

[0114] Table 4

[0115] Table 5

[0116] Table 6

[0117] Table 7

[0118] Table 8

[0119] Table 9

[0120] Table 10

[0121] Table 11

[0122] Table 12

[0123] Table 13

[0124] Table 14

[0125] Table 15

[0126] Table 16

[0127] Table 17

[0128] Table 18

[0129] Table 19

[0130] Table 20

[0131] Table 21

[0132] Table 22

[0133] Table 23

[0134] Table 24

[0135] [Table 25]

[0136] [Table 26]

[0137] [Table 27]

[0138] R 1 , R 2 , R 6 , R 8 , and R 9 is hydrogen, R 7 is methyl, X is oxygen, and R 3 , R 4 , R 5 Compounds of formula I.1, i.e., compounds I.1.1 to I.1.1944, in particular are preferred, where Q has the meaning defined in rows 1 to 1944 of Table 1 above, and Y is COOH.

[0139] R 1 , R 2 , R 6 , R 8 , and R 9 is hydrogen, R 7 X is methyl, X is oxygen, and R 3 , R 4 , R 5 Compounds of formula I.2, i.e., compounds I.2.1 to I.2.1944, in particular are preferred, where Q has the meaning defined in rows 1 to 1944 of Table 1 above, and Y is COOCH3.

[0140] R 1 , R 2 , R 6 , R 8 , and R 9 is hydrogen, R 7 is methyl, X is oxygen, and R 3 , R 4 , R5 Compounds of formula I.3, i.e., compounds I.3.1 to I.3.1944, in particular are preferred, where Q has the meaning defined in rows 1 to 1944 of Table 1 above, and Y is COOCH2CH3.

[0141] R 1 , R 2 , R 6 , R 8 , and R 9 is hydrogen, R 7 is methyl, X is oxygen, and R 3 , R 4 , R 5 Compounds of formula I.4, i.e., compounds I.4.1 to I.4.1944, in particular are preferred, where Q has the meaning defined in rows 1 to 1944 of Table 1 above, and Y is COOCH(CH3)2.

[0142] R 1 , R 2 , R 6 , R 8 , and R 9 is hydrogen, R 7 is methyl, X is oxygen, and R 3 , R 4 , R 5 Compounds of formula I.5, i.e., compounds I.5.1 to I.5.1944, in particular are preferred, where Q has the meaning defined in rows 1 to 1944 of Table 1 above, and Y is COOCH2CH(CH3)2.

[0143] R 1 , R 2 , R 6 , R 8 , and R 9 is hydrogen, R 7 is methyl, X is oxygen, and R 3 , R 4 , R 5 , and Q have the meanings defined in rows 1 to 1944 of Table 1 above, and Y is COOR e And R e Compounds of formula I.6, where cyclobutyl is present, i.e., individual compounds I.6.1 to I.6.1944, are particularly preferred.

[0144] R 1 , R 2 , R 6 , R 8 , and R 9 is hydrogen, R 7 is methyl, X is oxygen, and R 3 , R 4 , R 5 Compounds of formula I.7, i.e., compounds I.7.1 to I.7.1944, in particular are preferred, where Q has the meaning defined in rows 1 to 1944 of Table 1 above, and Y is COOCH2CH2OCH3.

[0145] R 1 , R 2 , R 6 , R 8 , and R 9 is hydrogen, R 7 is methyl, X is oxygen, and R 3 , R 4 , R 5 Compounds of formula I.8, i.e., compounds I.8.1 to I.8.1944, are particularly preferred, where Q has the meaning defined in rows 1 to 1944 of Table 1 above, and Y is COOCH2CH2SCH3.

[0146] R 1 , R 2 , R 6 , R 8 , and R 9 is hydrogen, R 7 is methyl, X is oxygen, and R 3 , R 4 , R 5 Compounds of formula I.9, i.e., compounds I.9.1 to I.9.1944, are particularly preferred, where Q has the meaning defined in rows 1 to 1944 of Table 1 above, and Y is COOCH2CH2SC6H5 (where C6H5 is phenyl).

[0147] R 1 , R 2 , R 6 , R 8 , and R 9 is hydrogen, R 7is methyl, X is oxygen, and R 3 , R 4 , R 5 Compounds of formula I.10, i.e., compounds I.10.1 to I.10.1944, in particular are preferred, where Q has the meaning defined in rows 1 to 1944 of Table 1 above, and Y is COOCH2CH2S(O)2C6H5 (where C6H5 is phenyl).

[0148] R 1 , R 2 , R 6 , R 8 , and R 9 is hydrogen, R 7 is methyl, X is oxygen, and R 3 , R 4 , R 5 Compounds of formula I.11, i.e., compounds I.11.1 to I.11.1944, in which Q has the meaning defined in rows 1 to 1944 of Table 1 above and Y is CONHCH2CH2OCH3, are particularly preferred.

[0149] R 1 , R 2 , R 6 , R 8 , and R 9 is hydrogen, R 7 is methyl, X is oxygen, and R 3 , R 4 , R 5 Compounds of formula I.12, i.e., compounds I.12.1 to I.12.1944, in which Q has the meaning defined in rows 1 to 1944 of Table 1 above and Y is CONHOCH3, are particularly preferred.

[0150] R 1 , R 2 , R 6 , R 8 , and R 9 is hydrogen, R 7 is methyl, X is oxygen, and R 3 , R 4 , R 5 , and Q have the meanings defined in rows 1 to 1944 of Table 1 above, and Y is CONR b Rh (In the formula, R b and R h Compounds of formula I.13, i.e., individual compounds I.13.1 to I.13.1944, are particularly preferred (these compounds, together with the nitrogen atom to which they are bonded, form a saturated six-membered heterocycle containing one oxygen atom adjacent to the nitrogen atom).

[0151] R 1 , R 2 , R 6 , R 8 , and R 9 is hydrogen, R 7 is methyl, X is oxygen, and R 3 , R 4 , R 5 Compounds of formula I.14, i.e., compounds I.14.1 to I.14.1944, in which Q has the meaning defined in rows 1 to 1944 of Table 1 above and Y is CONHCH(CH3)C(O)OCH3, are particularly preferred.

[0152] R 1 , R 2 , R 6 , R 8 , and R 9 is hydrogen, R 7 is methyl, X is oxygen, and R 3 , R 4 , R 5 Compounds of formula I.15, i.e., compounds I.15.1 to I.15.1944, in which Q has the meaning defined in rows 1 to 1944 of Table 1 above and Y is CONHCH2CH2OCH2CH2OCH3, are particularly preferred.

[0153] R 1 , R 2 , R 6 , R 8 , and R 9 is hydrogen, R 7 is methyl, X is oxygen, and R 3 , R 4 , R 5Compounds of formula I.16, i.e., compounds I.16.1 to I.16.1944, in particular are preferred, where Q has the meaning defined in rows 1 to 1944 of Table 1 above, and Y is CONHC(CH3)2CCH.

[0154] R 1 , R 2 , R 6 , R 8 , and R 9 is hydrogen, R 7 is methyl, X is oxygen, and R 3 , R 4 , R 5 Compounds of formula I.17, i.e., compounds I.17.1 to I.17.1944, in which Q has the meaning defined in rows 1 to 1944 of Table 1 above and Y is CONHS(O)2CH3, are particularly preferred.

[0155] R 1 , R 2 , R 6 , R 8 , and R 9 is hydrogen, R 7 is methyl, X is oxygen, and R 3 , R 4 , R 5 Compounds of formula I.18, i.e., compounds I.18.1 to I.18.1944, in particular are preferred, where Q has the meaning defined in rows 1 to 1944 of Table 1 above, and Y is CONHS(O)2CF3.

[0156] The compound of formula (I) according to the present invention can be prepared by a standard organic chemistry process, for example, the following process. General Scheme 1: [ka]

[0157] The compounds of formula (I) can be prepared according to methods described in the prior art or similar methods, are very well known, and general amide and peptide coupling techniques are applied. The synthesis utilizes starting materials that can be prepared according to conventional procedures, starting from commercially available or readily available compounds.

[0158] The compound of formula (I) can be prepared, for example, from the compound of formula (V) (where X=O, L=OH, Cl, or F; where X=S, L=Cl or F) and commercially available amino acids and esters (IV) according to scheme 1 to form benzoylaminoester (III). Such coupling reactions using acid chlorides and bases are described, for example, in Nadia, Klai; Malika, Berredjem; Nawel, Khettache; Med Yazid, Belghit; Zine, Regainia; Aouf, Nour-Eddine, J. Heterocyclic Chem., 41, 57 (2004) or in Chen, Francis MF; Benoiton, N. Leo, Can. J. Chem. 1987, 65, 1224-1227, and can be achieved using common coupling reagents such as EDC / HOBt in international publication brochure 2010 / 084979, or by using other coupling reagents, such as HATU (O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium-hexafluorophosphate) and organic bases.

[0159] To obtain the compound of formula (I), intermediate (III) can be converted to benzoyl amino acid (II) by applying a common saponification technique, such as treatment with a base, followed by a second coupling step with amine (VI) using a method common to those skilled in the art, similar to the one described above.

[0160] General Scheme 2: [ka] The compound of formula (I) can also be prepared, for example, from the compound of formula (V) (where X=O, L=OH, Cl, or F; where X=S, L=Cl, or F) and a suitable amino precursor VII using a coupling reaction similar to that described above and as illustrated below in the experimental section, according to Scheme 2.

[0161] General Scheme 3: [ka] Alternatively, the compound of formula (I) may undergo further saponification / coupling steps (Y=CO2R) as illustrated below in the experimental section. e It can be prepared by modifying compound (I) using ) as an example.

[0162] General Scheme 4: [ka] Thiamides of formula (I having X=S) can be prepared from the corresponding amides of formula (I having X=O) by using a thiolation reagent according to scheme 4.

[0163] Preferably, elemental sulfur (CAS: 7704-34-9), phosphorus pentasulfide (CAS: 1314-80-3), ammonium phosphorodithioate, or Lawson's reagent (CAS: 19172-47-5) is used. Most preferably, Lawson's reagent (CAS: 19172-47-5) is used.

[0164] The reaction is typically carried out in an organic solvent. Preferably, an aprotic organic solvent is used. Most preferably, tetrahydrofuran (THF), 1,4-dioxane, and toluene are used. The reaction is carried out at a temperature from room temperature to reflux temperature. Preferably, the reaction is carried out at reflux temperature.

[0165] Furthermore, it may be useful to apply the compound of formula (I) in combination with an antidote. The antidote is a compound that prevents or reduces damage to useful plants without significantly affecting the herbicidal effect of the compound of formula (I) on undesirable vegetation. This can be applied before sowing (transplanting) of useful plants (e.g., seed treatment, shoots, or seedlings), or either pre-germination or post-germination application. The antidote, the compound of formula (I), and an optional herbicide B can be applied simultaneously or sequentially.

[0166] In another embodiment of the present invention, the combination according to the present invention comprises at least one compound of formula (I) and at least one antidote C (component C).

[0167] Examples of antidotes include (quinoline-8-oxy)acetic acid, 1-phenyl-5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acid, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acid, 4.5-dihydro-5,5-diallyl-3-isoxazolecarboxylic acid, dichloroacetamide, α-oxyminophenylacetonitrile, acetophenoxime, 4,6-dihalo-2-phenylpyrimidine, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzoic acid amide, 1,8-naphthalene anhydride, 2-halo-4-(haloalkyl)-5-thiazolecarboxylic acid, phosphothiolates and N-alkyl-O-phenylcarbamates, and their agriculturally acceptable salts and agriculturally acceptable derivatives such as their amides, esters and thioesters, provided that they contain an acid group.

[0168] Examples of antidote compound C include benoxacol, croquintocet, siomethrinyl, cyprosulfamide, dichlormid, dicyclonone, dietholate, fenchlorazole, fenchlorim, flurazole, fluxofenim, flirazole, isoxadifen, mefenpyr, mefenate, anhydrous naphthalic acid, oxavethrinyl, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (R-29148, CAS52836-31-4), metcamifen, and BPCMS (CAS54091-06-4).

[0169] Active compound C is a known herbicide and antidote; see, for example, The Compendium of Pesticide Common Names (http: / / www.alanwood.net / pesticides / ); Farm Chemicals Handbook 2000 volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, RRSchmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; WHAhrens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994; and K.K. Hatzios, Herbicide Handbook, Supplement for the 7th edition, Weed Science Society of America, 1998.

[0170] The present invention also relates to a formulation comprising at least an auxiliary agent and at least one compound of formula (I) according to the present invention.

[0171] The formulation contains an effective amount of the compound of formula (I). The term "effective amount" refers to a combination or amount of compound (I) that is sufficient to control undesirable plants, particularly undesirable vegetation in crops (i.e., cultivated plants), without causing substantial damage to the treated crop plants. Such amounts can vary widely and depend on various factors, such as the undesirable vegetation to be controlled, the treated crop plants or materials, climatic conditions, and the specific compound of formula (I) used.

[0172] Compounds of formula (I) and their salts can be converted into conventional types of formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, presses, capsules, and mixtures thereof. Examples of formulation types include suspensions (e.g., SC, OD, FS), emulsifying concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME), capsules (e.g., CS, ZC), pastes, lozenges, wetting powders or dusts (e.g., WP, SP, WS, DP, DS), presses (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticides (e.g., LN), and gel formulations for the treatment of plant seedlings such as seeds (e.g., GF). These and further formulation types are defined in "Catalogue of pesticide formulation types and international coding system," Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.

[0173] The formulations are prepared by known methods, for example, as described in Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

[0174] Suitable auxiliary agents include solvents, liquid carriers, solid carriers or bulking agents, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, humidifiers, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, defoaming agents, colorants, tackifiers, and binders.

[0175] Suitable solvents and liquid carriers include water and organic solvents, for example, medium-to-high boiling mineral oil fractions, e.g., kerosene, diesel oil; oils of plant or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e.g., toluene, paraffin, tetrahydronaphthalene, alkylated naphthalene; alcohols, e.g., ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, e.g., cyclohexanone; esters, e.g., lactic acid esters, carbonate esters, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g., N-methylpyrrolidone, fatty acid dimethylamide; and mixtures thereof.

[0176] Suitable solid carriers or fillers include mineral soils, such as silicate, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, such as cellulose, starch; fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; plant-derived products, such as grain meal, bark meal, wood meal, nut meal, and mixtures thereof.

[0177] Suitable surfactants include surfactant compounds, such as anionic, cationic, nonionic, and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids, or adjuvants. Examples of surfactants are described in McCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

[0178] Suitable anionic surfactants are alkali salts, alkaline earth salts, or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates include alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates, or sulfosuccinates. Examples of sulfates include fatty acids and oils, ethoxylated alkylphenols, alcohols, ethoxylated alcohols, or fatty acid ester sulfates. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohols or alkylphenol ethoxylates.

[0179] Suitable nonionic surfactants include alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids, or fatty acid esters that have been alkoxylated in 1 to 50 equivalents. Ethylene oxide and / or propylene oxide, preferably ethylene oxide, can be used for alkoxylation. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters, or monoglycerides. Examples of sugar-based surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters, or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinylpyrrolidone, vinyl alcohol, or vinyl acetate.

[0180] Suitable cationic surfactants are quaternary surfactants, such as quaternary ammonium compounds having one or two hydrophobic groups or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are AB or ABA type block polymers containing blocks of polyethylene oxide and polypropylene oxide, or ABC type block polymers containing alkanols, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are polyacrylic acid or alkali salts of polyacid comb-type polymers. Examples of polybases are polyvinylamine or polyethyleneamine.

[0181] Suitable adjuvants are compounds that possess negligible or even zero insecticidal activity and enhance the biological performance of the compound of formula (I) on the target. Examples include surfactants, mineral oils or vegetable oils, and other adjuvants. Further examples are described in Knowles, Adjuvants and Additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

[0182] Suitable thickeners include polysaccharides (e.g., xanthan gum, carboxymethylcellulose), inorganic clay (organically modified or unmodified), polycarboxylates, and silicates.

[0183] Suitable fungicides include bronopol and isothiazolinone derivatives, such as alkylisothiazolinone and benzisothiazolinone.

[0184] Suitable antifreezes include ethylene glycol, propylene glycol, urea, and glycerin.

[0185] Suitable defoaming agents include silicones, long-chain alcohols, and fatty acid salts.

[0186] Suitable colorants (e.g., red, blue, or green) are low water-soluble pigments and water-soluble dyes. Examples include inorganic colorants (e.g., iron oxide, titanium dioxide, hexacyanoferrate) and organic colorants (e.g., alizarin-, azo-, and phthalocyanine colorants).

[0187] Suitable tackifiers or binders include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylate, biological wax or synthetic wax, and cellulose ether.

[0188] Examples of the types of formulations and their preparations are as follows: i) water-soluble concentrate (SL, LS) Dissolve 10 to 60% by weight of a compound of formula (I) according to the present invention or a combination comprising at least one compound of formula (I) (component A) and an antidote C (component C), and 5 to 15% by weight of a wetting agent (e.g., alcohol alkoxylate) in up to 100% by weight of water and / or a water-soluble solvent (e.g., alcohol). The active substance dissolves when diluted with water.

[0189] ii) Dispersed Concentrate (DC) Dissolve 5 to 25% by weight of a compound of formula (I) according to the present invention or a combination of at least one compound of formula (I) (component A) and an antidote C (component C), and 1 to 10% by weight of a dispersant (e.g., polyvinylpyrrolidone) in up to 100% by weight of an organic solvent (e.g., cyclohexanone). Dilution with water yields a dispersion.

[0190] iii) Emulsifiable concentrate (EC) Dissolve 15-70% by weight of a compound of formula (I) according to the present invention or a combination comprising at least one compound of formula (I) (component A) and an antidote C (component C), and 5-10% by weight of an emulsifier (e.g., calcium dodecylbenzenesulfonate, castor oil ethoxylate) in a remainder of up to 100% by weight of an insoluble organic solvent (e.g., aromatic hydrocarbon). Dilution with water yields an emulsion.

[0191] iv) Emulsions (EW, EO, ES) Dissolve 5-40% by weight of a compound of formula (I) according to the present invention or a combination of at least one compound of formula (I) (component A) and an antidote C (component C), and 1-10% by weight of an emulsifier (e.g., calcium dodecylbenzenesulfonate and castor oil ethoxylate) in 20-40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon). Introduce this mixture into water up to 100% by weight using an emulsifier to obtain a homogeneous emulsion. Dilution with water yields an emulsion.

[0192] v) Suspensions (SC, OD, FS) In a stirred ball mill, a combination of 20-60% by weight of the compound of formula (I) according to the present invention or at least one compound of formula (I) (component A) and antidote C (component C) is ground with the addition of 2-10% by weight of a dispersant and wetting agent (e.g., sodium lignosulfonate and alcohol ethoxylate), 0.1-2% by weight of a thickener (e.g., xanthan gum), and the remainder up to 100% by weight of water to obtain a fine active substance suspension. Dilution with water yields a stable suspension of the active substance. For FS-type formulations, up to 40% by weight of a binder (e.g., polyvinyl alcohol) is added.

[0193] vi) Water-dispersible granules and water-soluble granules (WG, SG) A combination of 50-80% by weight of a compound of formula (I) according to the present invention, or at least one compound of formula (I) (component A), and an antidote C (component C) is finely ground with the addition of up to 100% by weight of a dispersant and a wetting agent (e.g., sodium lignosulfonate and alcohol ethoxylate), and prepared as water-dispersible or water-soluble granules using technical equipment (e.g., extrusion, spray tower, fluidized bed). Dilution with water yields a stable dispersion or solution of the active substance.

[0194] vii) Water-dispersible powders and water-soluble powders (WP, SP, WS) A combination comprising 50-80% by weight of a compound of formula (I) according to the present invention, or at least one compound of formula (I) (component A), and an antidote C (component C) is ground in a rotor stator mill with the addition of 1-5% by weight of a dispersant (e.g., sodium lignosulfonate), 1-3% by weight of a wetting agent (e.g., alcohol ethoxylate), and up to 100% by weight of a solid carrier (e.g., silica gel). Dilution with water yields a stable dispersion or solution of the active substance.

[0195] viii) Gel formulations (GW, GF) In a stirred ball mill, a combination of 5 to 25% by weight of a compound of formula (I) according to the present invention or at least one compound of formula (I) (component A) and an antidote C (component C) is ground with the addition of 3 to 10% by weight of a dispersant (e.g., sodium lignosulfonate), 1 to 5% by weight of a thickener (e.g., carboxymethylcellulose), and the remainder up to 100% by weight of water to obtain a fine suspension of the active substance. Dilution with water yields a stable suspension of the active substance.

[0196] iv) Microemulsion (ME) To a combination comprising 5-20% by weight of a compound of formula (I) according to the present invention or at least one compound of formula (I) (component A) and an antidote C (component C), 5-30% by weight of an organic solvent blend (e.g., fatty acid dimethylamide and cyclohexanone), 10-25% by weight of a surfactant blend (e.g., alcohol ethoxylate and arylphenol ethoxylate), and water up to 100% of the remainder is added. The mixture is stirred for 1 hour to spontaneously form a thermodynamically stable microemulsion.

[0197] iv) Microcapsules (CS) An oil phase containing 5-50% by weight of a compound of formula (I) according to the present invention or a combination of at least one compound of formula (I) (component A) and an antidote C (component C), 0-40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon), and 2-15% by weight of an acrylic monomer (e.g., methyl methacrylate, methacrylic acid, and di or triacrylate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). By initiating radical polymerization with a radical initiator, poly(meth)acrylate microcapsules are formed. Alternatively, an oil phase containing 5-50% by weight of a compound of formula (I) according to the present invention, 0-40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon), and an isocyanate monomer (e.g., diphenylmethene-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). By adding a polyamine (e.g., hexamethylenediamine), polyurea microcapsules are formed. The amount of monomer is 1-10% by weight. The weight percentage refers to the total CS composition.

[0198] ix) Dust powder (DP, DS) A combination of 1 to 10% by weight of a compound of formula (I) according to the present invention or at least one compound of formula (I) (component A) and an antidote C (component C) is finely ground and tightly mixed with up to 100% by weight of a solid carrier (e.g., fine kaolin powder).

[0199] x) Granules (GR, FG) A combination comprising 0.5 to 30% by weight of a compound of formula (I) according to the present invention or at least one compound of formula (I) (component A) and an antidote C (component C) is finely ground and combined with a solid carrier (e.g., silicate) up to 100% by weight. Granulation is achieved by extrusion, spray drying, or fluidized bed.

[0200] xi) Ultra-trace liquid (UL) Dissolve a combination of 1 to 50% by weight of a compound of formula (I) according to the present invention or at least one compound of formula (I) (component A) and an antidote C (component C) in an organic solvent (e.g., aromatic hydrocarbon) up to 100% by weight.

[0201] Formulations of types i) to xi) may optionally contain further auxiliary agents, such as 0.1 to 1% by weight of a fungicide, 5 to 15% by weight of an antifreeze, 0.1 to 1% by weight of an antifoaming agent, and 0.1 to 1% by weight of a coloring agent.

[0202] The formulations and / or combinations generally contain 0.01 to 95% by weight, preferably 0.1 to 90% by weight, and particularly 0.5 to 75% by weight, of the compound of formula (I).

[0203] The compound of formula (I) is used with a purity of 90% to 100%, preferably 95% to 100% (as determined by NMR spectrum).

[0204] For the purpose of treating plant seedlings, especially seeds, seed treatment solutions (LS), emulsion suspensions (SE), flowable formulations (FS), dried seed treatment powders (DS), seed treatment slurry wettable powders (WS), seed treatment water-soluble powders (SS), seed treatment emulsions (ES), emulsifying concentrates (EC), and gel formulations (GF) are typically used. These formulations, after 2 to 10-fold dilution, provide an active substance concentration of 0.01 to 60% by weight, preferably 0.1 to 40% by weight, in a ready-to-use preparation. (Shifted downwards)

[0205] Methods for applying the compound of formula (I), its formulations, and / or combinations to plant seedlings, particularly seeds, include powdering, coating, pelletizing, dusting, soaking, and inter-row application. Preferably, the compound of formula (I), its formulations, and / or combinations are applied to plant seedlings in a manner that does not induce germination, such as seed dressing, pelletizing, coating, and dusting.

[0206] Compounds of formula (I), formulations containing them, and / or combinations thereof may be premixed with various types of oils, wetting agents, adjuvants, fertilizers, or micronutrients, or, where appropriate, may not be added until immediately before use (tank mix). These agents can be miscible with the formulations according to the present invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

[0207] The user typically applies the compound of formula (I) according to the present invention, formulations containing the same, and / or combinations thereof, from a pre-dosing device, napsack sprayer, spray tank, spray plane, or irrigation device. Typically, the formulation is brought to the desired application concentration using water, buffers, and / or further auxiliaries, thus obtaining a ready-to-use spray solution or formulation according to the present invention. Typically, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray solution is applied per hectare of agricultural area.

[0208] According to one embodiment, the individual components or partially premixed components of the formulation according to the present invention, such as the compound of formula (I) and components optionally containing an active substance from group C, are mixed by the user in a spray tank, and further auxiliaries and additives may be added as appropriate.

[0209] In further embodiments, the individual components of the formulation according to the present invention, such as part of a kit or part of a two- or three-component mixture, are mixed by the user themselves in a spray tank, and further additives may be added as appropriate.

[0210] In further embodiments, individual components or partially premixed components of the formulation according to the present invention, such as compounds of formula (I) and components optionally containing active substances from group C, can be applied together or sequentially (for example, after tank mixing).

[0211] The compound of formula (I) is suitable as a herbicide.

[0212] Compounds of formula (I) or formulations containing compounds of formula (I) are highly effective in controlling undesirable vegetation in non-agricultural land, particularly at high application rates. They act on broadleaf weeds and grass weeds of crops such as wheat, rice, maize, soybeans, and cotton without causing significant damage to the crop plants. This effect is mainly observed at low application rates.

[0213] The compounds of the present invention are useful for controlling the following weeds, for example: typical examples include Abutilon theophrasti (ABUTH), Alopercurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Apera spica-venti (APESV), Avena fatua (AVEFA), Digitaria sanguinalis (DIGSA), Echinocloa crus-galli (ECHCG), Chenopodium album (CHEAL), Lolium multiflorum (LOLMU), Setaria faberi (SETFA), and Setaria viridis (SETVI).

[0214] Compounds of formula (I) or formulations containing them are applied to plants primarily by spraying them onto the leaves. In this specification, application can be carried out by conventional spraying techniques, for example, using water as a carrier, with a spray volume of approximately 100-1000 l / ha (e.g., 300-400 l / ha). Compounds of formula (I) or formulations and / or combinations containing them may also be applied by low-volume or very-low-volume methods, or in the form of fine particles.

[0215] The compound of formula (I), or formulations containing them, can be applied before, during, and / or after the appearance of undesirable vegetation, preferably during and / or after its appearance.

[0216] The compound or formulation of formula (I) may be applied before or during sowing.

[0217] Compounds of formula (I), or formulations containing them, can be applied before emergence, after emergence, before planting, or together with the seeds of crop plants. It is also possible to apply compounds of formula (I) or formulations thereof by applying seeds of crop plants that have been pretreated with compounds of formula (I) or formulations thereof. If the active ingredient is not well tolerated by certain crop plants, application techniques may be used in which the formulation is sprayed with the assistance of a sprayer so as not to come into contact with the leaves of sensitive crop plants as possible, but the active ingredient reaches the leaves of undesirable vegetation growing below or the bare soil surface (post-direct, lay-by).

[0218] In further embodiments, compounds of formula (I), or formulations containing them, can be applied by treating seeds. The seed treatment essentially includes all procedures well known to those skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed covering, seed dripping, and seed pelletizing) based on compounds of formula (I), or formulations prepared therefrom.

[0219] The term "seed" includes all kinds of seeds, such as corn, seeds, fruits, tubers, seedlings, and similar forms. In this specification, the term "seed" preferably refers to grain seeds and seeds of cereals. The seeds used may be the seeds of the crop plants described above, but may also be the seeds of transgenic plants or plants obtained by conventional breeding methods.

[0220] When used for plant protection, the amount of the active substance without compounding agents, i.e., the compound of formula (I), and, if appropriate, component C, is 0.001 to 2 kg per hectare, preferably 0.005 to 2 kg, more preferably 0.05 to 0.9 kg, and particularly 0.1 to 0.75 kg, depending on the type of effect desired.

[0221] In another embodiment of the present invention, the application rate of the compound of formula (I), and optionally component C, is 0.001 to 3 kg / ha, preferably 0.005 to 2.5 kg / ha, and particularly 0.01 to 2 kg / ha, relative to the active substance (as).

[0222] In another preferred embodiment of the present invention, the application rate of the compound of formula (I) according to the present invention (total amount of the compound of formula (I)) is 0.1 g / ha to 3000 g / ha, preferably 10 g / ha to 1000 g / ha, depending on the target of control, season, target plant and growth stage.

[0223] In another preferred embodiment of the present invention, the application rate of the compound of formula (I) is in the range of 0.1 g / ha to 5000 g / ha, preferably in the range of 1 g / ha to 2500 g / ha or 5 g / ha to 2000 g / ha.

[0224] In another preferred embodiment of the present invention, the application rate of the compound of formula (I) is 0.1 to 1000 g / ha, preferably 1 to 750 g / ha, and more preferably 5 to 500 g / ha.

[0225] The required application amount of antidote C is generally in the range of 0.0005 kg / ha to 2.5 kg / ha, preferably in the range of 0.005 kg / ha to 2 kg / ha or 0.01 kg / ha to 1.5 kg / h.

[0226] In the treatment of plant seedlings such as seeds, for example, by dusting, coating, or drenching seeds, it is generally necessary to use an amount of active substance of 0.1 to 1000 g, preferably 1 to 1000 g, more preferably 1 to 100 g, and most preferably 5 to 100 g per 100 kilograms of plant seedlings (preferably seeds).

[0227] In another embodiment of the present invention, to treat the seeds, the amount of the active substance, i.e., the compound of formula (I), and, if appropriate, component C, is generally used in an amount of 0.001 to 10 kg per 100 kg of seeds.

[0228] When used for protecting materials or stored products, the amount of active substance applied depends on the type of application area and the desired effect. A commonly applied amount for protecting materials is 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of the active substance per cubic meter of treated material.

[0229] In the case of the combination according to the present invention, it is not important whether the compound of formula (I) and / or component C are formulated and applied together or separately. In the case of separate applications, the order in which they are applied is not particularly important. It is only necessary that the compound of formula (I) and / or component C are applied within a time frame that allows for the simultaneous action of the active ingredients on the plant, preferably within a time frame of up to 14 days, and especially within a time frame of up to 7 days.

[0230] Depending on the application, compounds of formula (I), or formulations containing them, can be additionally used on a wider range of crop plants to eliminate undesirable vegetation. Examples of suitable crops include: Onion (Allium cepa), pineapple (Ananas comosus), peanut (Arachis hypogaea), asparagus (Asparagus officinalis), oat (Avena sativa), beet variety altissima (sugar beet) (Beta vulgaris spec. altissima), beet variety rapa (turnip) (Beta vulgaris spec. rapa), rapeseed variety napus (rapeseed) (Brassica napus var. napus), rapeseed variety napobrassica (rutabaga) (Brassica napus var. napobrassica), rapeseed variety silvastris (winter tunic rape) (Brassica rapa var.silvestris), wild cabbage (Brassica oleracea), black mustard (Brassica nigra), tea plant (Camellia sinensis), safflower (Carthamus tinctorius), pecan (Carya illinoinensis), lemon (Citrus limon), orange (Citrus sinensis), Arabica coffee plant (Coffea arabica) (Robusta coffee plant (Coffea canephora), Liberica coffee plant (Coffea liberica)), cucumber (Cucumis sativus), Bermuda grass (Cynodon dactylon), wild carrot (Daucus carota), Guinea oil palm (Elaeis guineensis), wild strawberry (Fragaria vesca), soybean (Glycine max), and peanut (Gossypium). hirsutum) (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), sunflower (Helianthus annuus), rubber tree (Hevea brasiliensis), barley (Hordeum vulgare), hops (Humulus lupulus), sweet potato (Ipomoea batatas), walnut (Juglans regia), lentil (Lens culinaris), flax (Linum usitatissimum), tomato (Lycopersicon lycopersicum), apple (Malus spec.), cassava (Manihot esculenta), alfalfa (Medicago sativa), banana (Musa spec.), tobacco (Nicotiana Tabacum (N. rustica), olive (Olea europaea), rice (Oryza sativa), lima bean (Phaseolus lunatus), green bean (Phaseolus vulgaris), European spruce (Picea abies), pine (Pinus spec.)), pistachios (Pistacia vera), peas (Pisum sativum), sweet cherry (Prunus avium), peaches (Prunus persica), pears (Pyrus communis), apricots (Prunus armeniaca), black cherry (Prunus cerasus), almonds (Prunus dulcis) and plums (Prunus domestica), Ribes sylvestre, castor beans (Ricinus communis), sugarcane (Saccharum officinarum), rye (Secale cereale), white mustard (Sinapis alba), potatoes (Solanum tuberosum), sorghum (Sorghum bicolor (s. vulgare)), cocoa (Theobroma) Cacao, red clover (Trifolium pratense), bread wheat (Triticum aestivum), rye wheat (Triticale), durum wheat (Triticum durum), broad bean (Vicia faba), European grape (Vitis vinifera), and maize (Zea mays).

[0231] Preferred crops include peanuts (Arachis hypogaea), beets (Beta vulgaris spec. altissima), rapeseed (Brassica napus var. napus), wild cabbage (Brassica oleracea), lemons (Citrus limon), oranges (Citrus sinensis), Arabica coffee plants (Coffea arabica, Robusta coffee plants, Liberica coffee plants), Bermuda grass (Cynodon dactylon), soybeans (Glycine max), and Asian cotton (Gossypium hirsutum, Gossypium arboreum, Gossypium hirsutum). herbaceum), Gossypium vitifolium, sunflower (Helianthus annuus), barley (Hordeum vulgare), walnut (Juglans regia), lentil (Lens culinaris), flax (Linum usitatissimum), tomato (Lycopersicon lycopersicum), apple (Malus spec.), alfalfa (Medicago sativa), tobacco (Nicotiana tabacum) (N. rustica), olive (Olea europaea), rice (Oryza sativa), lima bean (Phaseolus lunatus), kidney bean (Phaseolus vulgaris), pistachio (Pistacia vera), pea (Pisum sativum), almond (Prunus dulcis), sugarcane (Saccharum officinarum), rye (Secale cereale), potato (Solanum tuberosum), sorghum (Sorghum bicolor (s.g., grugare (s.g.These include vulgare, rye wheat (Triticale), bread wheat (Triticum aestivum), durum wheat (Triticum durum), broad bean (Vicia faba), European grape (Vitis vinifera), and maize (Zea mays).

[0232] Particularly preferred crops are cereals, corn, soybeans, rice, rapeseed, cotton, potatoes, peanuts, or perennial crops.

[0233] The compounds of formula (I) according to the present invention, or formulations containing them, can also be used in crops modified by mutagenesis or genetic engineering to provide new traits to plants or to modify existing traits.

[0234] As used herein, the term “crop” also includes (crop) plants that have been modified by mutagenesis or genetic engineering to provide new traits to the plant or to alter existing traits.

[0235] Mutagenesis includes techniques for random mutagenesis using X-rays or mutagenic chemicals, as well as techniques for targeted mutagenesis aimed at inducing mutations at specific gene loci in the plant genome. Targeted mutagenesis techniques often achieve their target effect using oligonucleotides or proteins such as CRISPR / Cas, zinc finger nucleases, TALENs, or meganucleases.

[0236] Genetic engineering typically uses recombinant DNA technology to create modifications to plant genomes that cannot be easily obtained in the natural environment through crossbreeding, mutagenesis, or natural recombination. Typically, one or more genes are incorporated into the plant genome to add or improve traits. These incorporated genes are also called transgenes in this art, and plants containing such transgenes are called transgenic plants. In the process of plant transformation, several transformation events usually occur in which the introduced gene is incorporated into different genomic loci. A plant containing a specific introduced gene at a specific genomic locus is usually described as having contained a specific “event,” which is referred to by a specific event name. Examples of traits introduced or modified in plants include herbicide resistance, insect resistance, increased yield, and tolerance to abiotic conditions such as drought.

[0237] Herbicide resistance is produced through mutagenesis and genetic engineering. Plants resistant to acetolactate synthase (ALS) inhibitor herbicides through conventional mutagenesis and breeding methods include plant varieties marketed under the Clearfield® name. However, the majority of herbicide resistance traits are produced through the use of transgenes.

[0238] Herbicide resistance has been developed against glyphosate, glufosinate, 2,4-D, dicamba, oxynyl herbicides (such as bromoxynil and ioxynil), sulfonylurea herbicides, ALS inhibitor herbicides, and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors (such as isoxaflutol and mesotrione).

[0239] Transgenes used to provide herbicide resistance traits include: transgenes for resistance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621 and goxv247; transgenes for resistance to glufosinate: pat and bar; transgenes for resistance to 2,4-D: aad-1 and aad-12; transgene for resistance to dicamba: dmo; transgene for resistance to oxynyl herbicides: bxn; transgenes for resistance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA; transgenes for resistance to ALS inhibitor herbicides: csr1-2; transgenes for resistance to HPPD inhibitor herbicides: hppdPF, W336 and avhppd-03.

[0240] Transgenic cone events containing herbicide resistance genes include, for example, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHG0JG, HCEM485, VCO-Φ1981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507, and TC6275, although these do not exclude others.

[0241] Transgenic soybean events containing herbicide resistance genes include, for example, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHTφH2, W62, W98, FG72, and CV127, although these do not exclude others.

[0242] Transgenic cotton events containing herbicide resistance genes include, for example, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3, and T304-40, although these do not exclude others.

[0243] Transgenic canola events containing herbicide resistance genes include, for example, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2, and RF3, although these do not exclude others.

[0244] Insect resistance is primarily generated by transferring bacterial genes for insecticidal proteins into plants.

[0245] The most frequently used transgenes are toxin genes from Bacillus species and their synthetic mutants, such as cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A(a), and vip3Aa20. However, plant-derived genes have also been translocated to other plants, particularly genes encoding protease inhibitors such as CpTI and pinII. A further approach involves using transgenes to generate double-stranded RNAs that target and downregulate insect genes in plants. An example of such a transgene is dvsnf7.

[0246] Transgenic cone events containing genes for insecticidal proteins or double-stranded RNA include, for example, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418, and MZIR098, but do not exclude others.

[0247] Transgenic soy events containing genes for insecticidal proteins include, for example, MON87701, MON87751, and DAS-81419, although this does not exclude others.

[0248] Transgenic cotton events containing genes for insecticidal proteins include, but are not excluded, SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Event1, COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119, and SGK321.

[0249] Yield increases are achieved by increasing ear biomass using the transgene athb17 present in corn event MON87403, or by improving photosynthesis using the transgene bbx32 present in soybean event MON87712.

[0250] Transgenes gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A, and fatb1-A have been used to create crops with improved oil content. Soybean events containing at least one of these genes are 260-05, MON87705, and MON87769.

[0251] Tolerance to abiotic conditions, particularly drought tolerance, is conferred by using the transgene cspB contained in corn event MON87460 and by using the transgene Hahb-4 contained in soybean event IND-φφ41φ-5.

[0252] Trait combinations are often achieved by combining genes involved in transformation events or by combining different events during the breeding process. Preferred trait combinations include herbicide resistance to various groups of herbicides, insect resistance to various types of insects, specifically resistance to lepidopteran and coleopteran insects, combinations of herbicide resistance with one or more insect resistances, combinations of herbicide resistance with increased yield, and combinations of herbicide resistance with resistance to abiotic conditions.

[0253] Plants containing single traits or stacked traits, as well as the genes and events that confer these traits, are publicly known in the art. For example, detailed information on the mutant or incorporated genes and their respective events is available from the websites of the International Service for the Acquisition of Agri-biotech Applications (ISAAA) (http: / / www.isaaa.org / gmapprovaldatabase) and the Center for Environmental Risk Assessment (CERA) (http: / / cera-gmc.org / GMCropDatabase), as well as from patent applications such as European Patent No. 3028573 and International Publication No. 2017 / 011288.

[0254] By using a compound of formula (I) according to the present invention, or a formulation or combination containing the same, on a crop, crop-specific effects can be obtained that include specific genes or events. These effects may include changes in growth behavior or resistance to biological or abiotic stressors. These effects may include, in particular, increased yield, improved resistance or tolerance to insects, nematodes, fungi, bacteria, mycoplasmas, viruses, or viroid pathogens, as well as early vigor, early or late maturation, low or high temperature tolerance, and changes in the amino acid or fatty acid spectrum or content.

[0255] Furthermore, the use of recombinant DNA technology also applies to plants containing modified or new components, particularly those that improve raw material production, such as potatoes that produce increased amounts of amylopectin (e.g., Amflora® potato, BASF SE, Germany).

[0256] Furthermore, it has been found that the compound of formula (I) or formulations containing the same according to the present invention is also suitable for drying the leaves and / or parts of the plant body of crops such as cotton, potato, rapeseed, sunflower, soybean, or broad bean, particularly cotton. In connection with this, formulations for drying and / or deliquing crops, processes for preparing such formulations, and methods for drying and / or deliquing plant bodies using the compound of formula (I) have been found.

[0257] Compounds of formula (I) are particularly suitable as desiccants for drying the above-ground parts of crop plants such as potatoes, rapeseed, sunflowers, and soybeans, as well as cereals. This enables the complete mechanical harvesting of these important crop plants.

[0258] Furthermore, there is economic interest in promoting harvests, which can be achieved by concentrating the reduction of dehiscence or attachment to trees of citrus fruits, olives, and other pernicious fruits, drupes, and nuts within a certain period of time. The same mechanism, namely promoting the development of abscission layer tissue between the fruit or leaf portion and the shoot portion of a plant, is also essential for regulating leaf fall in useful plants, especially cotton.

[0259] Furthermore, shortening the time it takes for individual cotton plants to mature improves the quality of the fibers after harvest. [Examples]

[0260] A. Synthesis Examples Chemical bonds depicted as bars in a chemical formula represent the relative stereochemistry on a ring system.

[0261] Examples of preparation of intermediates (II) and (III) Methyl(2R)-2-[(3,5-dichlorobenzoyl)amino]propanoate [ka] A solution of 3,5-dichlorobenzoyl chloride (28.3 g, 135 mmol) in dichloromethane (50 mL) was added to a mixture of methyl(2R)-2-aminopropanoate hydrochloride (18.8 g) and triethylamine (27.3 g, 270 mmol) in dichloromethane (250 mL), and the mixture was stirred at room temperature ("RT") for 3 hours. The mixture was then washed with hydrochloric acid (200 mL), water (3 × 400 mL), and brine (150 mL). The organic phase was dried on magnesium sulfate and concentrated under vacuum to obtain the product in quantitative yield. ¹H NMR: (400 MHz, deuterium-THF)δ 8.1(¹H), 7.8(s, ²H), 7.6(s, ¹H), 4.65(¹H), 3.65(s, ³H), 1.45(d, ³H)

[0262] (2R)-2-[(3,5-dichlorobenzoyl)amino]propanoic acid [ka] A solution of methyl(2R)-2-[(3,5-dichlorobenzoyl)amino]propanoate (37.1 g, 134 mmol) was treated with potassium hydroxide solution in methanol (1 M, 150 mL) at room temperature and stirred under reflux for 2 hours. Water (100 mL) was added, and most of the methanol was removed under vacuum. The pH was adjusted to 1-2 by adding hydrochloric acid (1 M), which caused the formation of a precipitate. Further water was added, and stirring was continued for 30 minutes. The product was obtained by filtration, washing with water, and drying in a vacuum drying cabinet (33.0 g, 94%) at 50°C. ¹H NMR: (400 MHz, deuterium-DMSO)δ ca. 12.6 (br s, ¹H), 8.9 (¹H), 7.9 (s, ²H), 7.8 (s, ¹H), 4.4 (m, ¹H), 1.4 (m, ³H).

[0263] Using this saponification method, partial isomerization was observed to varying degrees depending on the reaction conditions. The following alternative methods are less prone to isomerization:

[0264] Saponification substitute 1: (2R)-2-[(3,5-dichlorobenzoyl)amino]propanoic acid [ka] To a solution of methyl(2R)-2-[(3,5-dichlorobenzoyl)amino]propanoate (3.50 g, 12.7 mmol) in 50 mL of dichloromethane, hydroxy(trimethyl) stannane (4.58 g, 25.4 mmol) was added, and the reaction mixture was stirred under reflux for approximately 3 days. The reaction mixture was further diluted with 50 mL of dichloromethane, and aqueous hydrochloric acid (1 mol / L, 100 mL) was added. The resulting precipitate was separated by filtration. The remainder was dried overnight at 45°C under vacuum to obtain the title compound (2.85 g, 86%). The retention of the stereochemistry was confirmed by chiral LC.

[0265] (2S)-2-[(3,5-dichlorobenzoyl)amino]propanoic acid [ka] To a 250 mL solution of methyl(2S)-2-[(3,5-dichlorobenzoyl)amino]propanoate (5.47 g, 19.8 mmol) in dichloromethane, hydroxy(trimethyl) stannane (7.16 g, 39.6 mmol) was added, and the reaction mixture was stirred under reflux for 1 day. The reaction mixture was diluted with 200 mL of dichloromethane, and aqueous hydrochloric acid (1 mol / L, 200 mL) was added. The resulting precipitate was separated by filtration and washed with dichloromethane and water. The remainder was dried overnight at 45°C under vacuum to obtain the title compound (5.1 g, 97%).

[0266] Saponification substitute 2: (2R)-2-[(3,5-dichlorobenzoyl)amino]propanoic acid [ka] To a 100 mL solution of tert-butyl(2R)-2-[(3,5-dichlorobenzoyl)amino]propanoate (19.5 g, 61.3 mmol) in dichloromethane, trifluoroacetic acid (70 g, 10 equivalents) was added, and the reaction mixture was stirred at room temperature for approximately 20 hours. The reaction mixture was poured into water (400 mL). The resulting precipitate was separated by filtration and dried under vacuum at 45°C to obtain the title compound (15.9 g, 99%).

[0267] The precursor tert-butyl ester can be prepared, for example, by following the procedure below: tert-butyl(2S)-2-[(3,5-difluorobenzoyl)amino]propanoate [ka] Triethylamine was added to a 250 mL solution of tert-butyl(2S)-2-aminopropanoate hydrochloride (18.1 g, 100 mmol) in dichloromethane at room temperature, followed by the addition of a 3,5-difluorobenzoyl chloride (17.6 g, 100 mmol) solution in dichloromethane (50 mL). The reaction mixture was stirred for 2 hours, then washed with aqueous hydrochloric acid (1 mol / L, 150 mL), water (2 × 300 mL), and brine (100 mL). The organic phase was concentrated and dried under vacuum to obtain the title compound (27.7 g). ¹H NMR: (400 MHz, deuterium-DMSO)δ 8.85 (¹H), 7.6 (²H), 7.5 (¹H), 4.35 (¹H), 1.35-1.45 (¹²H).

[0268] Example of preparation of amino precursor VII Step 1: Methyl(1S,4R)-4-[[(2R)-2-(tert-butoxycarbonylamino)propanoyl]amino]cyclopent-2-ene-1-carboxylate [ka] (2R)-2-(tert-butoxycarbonylamino)propanoic acid (30.0 g, 159 mmol), methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride (29.6 g, 166 mmol), and N,N-diisopropylethylamine (61.5 g, 476 mmol) were mixed in 200 mL of dichloromethane. [dimethylamino(triazolo[4,5-b]pyridine-3-yloxy)methylene]-dimethyl-ammonium hexafluorophosphate (HATU, 63.3 g, 166 mmol) was added at room temperature. The suspension formed initially was heated under reflux and became clear after a few minutes. Stirring was continued at the same temperature for 2 hours. After cooling to room temperature, the organic phase was washed with water (3 × 500 mL), concentrated under vacuum to obtain the crude product, which was purified by column chromatography to obtain the title compound in 90% yield. 1H NMR:(400MHz,DMSO)δ 7.8(d,1H),6.8(d,1H)5.9(m,1H),5.7(m,1H),4.8(m,1H),3.95(m,1H),3. 65(s,3H),3.55(m,1H),2.5(m,1H),1.75(m,1H),1.35(s,9H),1.15(d,3H)

[0269] Step 2: Methyl(1S,4R)-4-[[(2R)-2-aminopropanoyl]amino]cyclopent-2-ene-1-carboxylate [ka] 90.2 g, 289 mmol of methyl(1S,4R)-4-[[(2R)-2-(tert-butoxycarbonylamino)propanoyl]amino]cyclopent-2-ene-1-carboxylate (90.2 g, 289 mmol) was dissolved in 250 mL of dichloromethane, to which 2,2,2-trifluoroacetic acid (230 g, 2 mol) was added at room temperature. The reaction mixture was heated under reflux for 1 day. The reaction mixture was carefully quenched with aqueous sodium hydroxide solution (4 mol / L, 400 mL) to adjust the pH to 8.5 and extracted with DCM (6 × 200 mL). The combined organic phases were dried under vacuum to obtain the product (37.4 g, 61%). (400MHz,DMSO)δ 7.85(d,1H),5.9(m,1H),5.75(m,1H),4.8(m,1H),3.65(s,3H),3.55(m,1H),3.2(m.1H),2.45(m,1H),1.8(br s,2H),1.7(m,1H),1.1(d,3H).

[0270] Example 1 (Compound I.3): Methyl(1S,4R)-4-[[(2R)-2-[(3,5-dichlorobenzoyl)amino]propanoyl]amino]cyclopento-2-ene-1-carboxylate [ka] (2R)-2-[(3,5-dichlorobenzoyl)amino]propanoic acid (500 mg, 1.91 mmol), methyl (1S,4R)-4-aminocyclopent-2-en-1-carboxylate hydrochloride (390 mg, 2.2 mmol), and HATU (2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, CAS[148893-10-1]) (834 mg, 2.2 mmol) were dissolved in DMF (6 mL) and diisopropylamine (986 mg, 7.36 mmol) was added. The mixture was stirred at room temperature for 4 hours. The solution was treated with ethyl acetate (50 mL) and washed with water (2 × 50 mL). The organic phase was dried on magnesium sulfate and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography to obtain 340 mg (46%) of the product. ¹H NMR: (400 MHz, deuterium-THF)δ 8.05(m,¹H), 7.8(s,²H), 7.6(s,¹H), 7.4(m,¹H), 5.9-5.75(m,²H), 4.95(m,¹H), 4.55(m,¹H), 3.65(s,³H), 3.5(m,¹H), 2.5(m,¹H), 1.8(m,¹H), 1.35(d,³H)

[0271] Alternative preparation of Example 1 (Compound I.3) [ka] To a solution of methyl(1S,4R)-4-[[(2R)-2-aminopropanoyl]amino]cyclopent-2-ene-1-carboxylate (4.25 g, 20 mmol) and N-ethyl-N-isopropyl-propan-2-amine (Hünig base, 5.17 g, 40 mmol) in 80 mL of DCM, a solution of 3,5-dichlorobenzoyl chloride (4.40 g, 21.0 mmol) in 20 mL of LDC was added at room temperature over 10 minutes, and the mixture was stirred for 3.5 hours. The reaction mixture was then treated with an excess of aqueous hydrochloric acid (1 mol / L) and washed with water (2x) and brine (1x). The organic phase was concentrated under vacuum. The crude product (8.3 g) was recrystallized from ethyl acetate to obtain methyl (1S,4R)-4-[[(2R)-2-[(3,5-dichlorobenzoyl)amino]propanoyl]amino]cyclopento-2-ene-1-carboxylate as a white solid (5.60 g, 14.5 mmol, 71%).

[0272] Example 2 (Compound I.5): Methyl(1S,4R)-4-[[(2R)-2-[(3,5-difluorobenzoyl)amino]propanoyl]amino]cyclopento-2-ene-1-carboxylate [ka] (2R)-2-[(3,5-difluorobenzoyl)amino]propanoic acid (500 mg, 2.18 mmol), methyl (1S,4R)-4-aminocyclopent-2-en-1-carboxylate hydrochloride (446 mg, 2.51 mmol), and HATU (2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, CAS[148893-10-1]) (954 mg, 2.51 mmol) were dissolved in DMF (5 mL) and diisopropylamine (564 mg, 4.36 mmol) was added. The mixture was stirred at room temperature for 18 hours. The solution was concentrated under vacuum, treated with ethyl acetate, and washed with water (2 × 10 mL). The organic phase was dried on magnesium sulfate and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography to obtain 350 mg (46%) of the product.

[0273] Alternative preparation of Example 2 (Compound I.5) [ka] To a solution of methyl(1S,4R)-4-[[(2R)-2-aminopropanoyl]amino]cyclopent-2-ene-1-carboxylate (20.2 g, 95.0 mmol) and N-ethyl-N-isopropyl-propan-2-amine (Hünig base, 24.6 g, 190 mmol) in 200 mL of DCM, a solution of 3,5-difluorobenzoyl chloride (17.6 g, 99.8 mmol) in 50 mL of DCM was added at room temperature, and the mixture was stirred for 2 hours. The reaction mixture was then treated with an excess of aqueous hydrochloric acid (1 mol / L) and washed with water (2x) and brine (1x). The organic phase was concentrated under vacuum. The crude product (37 g) was purified by chromatography to obtain methyl(1S,4R)-4-[[(2R)-2-[(3,5-difluorobenzoyl)amino]propanoyl]amino]cyclopent-2-ene-1-carboxylate (17.7 g, 53%). 1H NMR:(400MHz,CDCl3)δ 7.4(m,2H),7.1(m,1H),6.95(m,1H),6.8(m,1H),5.9(m,2H),5.05(m,1H), 4.65(m,1H),3.7(s,3H),3.55(m,1H),2.45(m,1H),1.9(m,1H),1.5(d,3H)

[0274] Example 3 (Compound I.158): (1S,4R)-4-[[(2S)-2-[(3,5-difluorobenzoyl)amino]propanoyl]amino]cyclopento-2-ene-1-carboxylic acid [ka] To a 250 mL solution of methyl(1S,4R)-4-[[(2S)-2-[(3,5-difluorobenzoyl)amino]propanoyl]amino]cyclopent-2-ene-1-carboxylate (15.1 g, 42.9 mmol) in dichloromethane, hydroxy(trimethyl) stannane (15.5 g, 85.7 mmol) was added, and the reaction mixture was stirred under reflux for 4 days. The reaction mixture was diluted with 200 mL of dichloromethane, and aqueous hydrochloric acid (2 mol / L, 150 mL) was added. The resulting precipitate was separated by filtration and washed with dichloromethane and plenty of water. The remainder was dried overnight in vacuum at 45°C to obtain the title compound (14.2 g, 98%). 1H NMR:(400MHz,DMSO)δ ca.12.4(br s,1H),8.65(d,1H),8.1(d,1H)7.6(m,2H),7.45(m,1H),5.9(m,1H),5.75(m,1 H),4.8(m,1H),4.45(m,1H),3.45(m,1H),2.45(m,1H),1.7(m,1H),1.35(d,3H)

[0275] Example 4 (Compound I.93): 3,5-Difluoro-N-[(1S)-1-methyl-2-oxo-2-[[(1R,4S)-4-(trifluoromethylsulfonylcarbamoyl)cyclopento-2-en-1-yl]amino]ethyl]benzamide [ka] To a solution of (1S,4R)-4-[[(2S)-2-[(3,5-difluorobenzoyl)amino]propanoyl]amino]cyclopent-2-en-1-carboxylic acid (400 mg, 1.18 mmol) in dichloromethane (10 mL), trifluoromethanesulfonamide (194 mg, 1.3 mmol), diisopropylethylamine (458 mg, 3.6 mmol), and HATU (2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate CAS [148893-10-1]), (495 mg, 1.3 mmol) were added and the mixture was stirred at room temperature for 2 hours. Dichloromethane (10 mL) was added, and the reaction mixture was washed with water (2 × 20 mL). The organic phase was separated, dried overnight in vacuum at 45°C, and the remainder was purified by column chromatography to obtain the title compound (260 mg). ¹H NMR: (400 MHz, DMSO) δ 8.65(d,¹H), 8.1(d,¹H), 7.6(m,²H), 7.45(m,¹H), 5.9(m,¹H), 5.7(m,¹H), 4.75(m,¹H), 4.4(m,¹H), 3.45(m,¹H), 2.4(m,¹H), 1.7(m,¹H), 1.3(d,³H)

[0276] Similar to the above example, R 1 , R 8 , and R 9 is hydrogen, R 7 The compound of formula (I) below, in which is methyl and X is oxygen, was prepared using a commercially available amine. # The absolute configuration (R or S) of a chiral carbon atom labeled with is provided. [ka] MZ: is the LC-MS-MZ mass-to-charge ratio; Et = ethyl.

[0277] [Table 28]

[0278] [Table 29]

[0279] Table 30

[0280] Table 31

[0281] Table 32

[0282] Table 33

[0283] Table 34

[0284] Table 35

[0285] Table 36

[0286] Table 37

[0287] Table 38

[0288] Table 39

[0289] [Table 40]

[0290] [Table 41]

[0291] [Table 42]

[0292] Similar to the above example, R 1 and R 8 The compound of formula (I) below, where is hydrogen and X is oxygen, was prepared using a commercially available amine. # The absolute configuration (R or S) of a chiral carbon atom labeled with is provided. [ka] MZ: stands for LC-MS-MZ, mass-to-charge ratio; rac. = racemic; Me is methyl; Et is ethyl.

[0293] [Table 43]

[0294] [Table 44]

[0295] [Table 45]

[0296] [Table 46]

[0297] [Table 47]

[0298] [Table 48]

[0299] [Table 49]

[0300] Similar to the above example, R 1 and R 8 is hydrogen, R 7 and R 9 However, these atoms, together with the carbon atoms to which they are bonded, form a 3- or 4-membered saturated carbon ring, and compounds of the following formula (I), where X is oxygen, were prepared using commercially available amines. # The absolute configuration (R or S) of a chiral carbon atom labeled with is provided. [ka] MZ: is the LC-MS-MZ mass-to-charge ratio;

[0301] [Table 50]

[0302] [Table 51]

[0303] [Table 52]

[0304] Similar to the above example, R 7 is methyl, and R 6 , R 8 , and R 9The compound of formula (I) below, where is hydrogen and X is oxygen, was prepared using a commercially available amine. # The absolute configuration (R or S) of a chiral carbon atom labeled with is provided. [ka] MZ stands for LC-MS-MZ, the mass-to-charge ratio; rac. = racemic; Me stands for methyl.

[0305] [Table 53]

[0306] [Table 54]

[0307] [Table 55]

[0308] B. Biological Examples The herbicidal activity of the compound of formula (I) was demonstrated by the following greenhouse experiment: Plastic flower pots were used as culture medium containers, and loamy sandy soil containing approximately 3.0% humus was added as a substrate. Seeds of the test plants were sown according to species. For pre-germination treatment, the active ingredient was suspended or emulsified in water and applied directly after sowing using a finely distributing nozzle. To promote germination and growth, the containers were gently watered and then covered with a transparent plastic cover until the test plants rooted. This cover resulted in uniform germination, provided that uniform germination of the test plants was not impaired by the active ingredient. Regarding post-germination treatment, the test plants were first allowed to grow to a height of 3-15 cm, according to their characteristics, before being treated with the active ingredient suspended or emulsified in water. For this purpose, the test plants were either sown directly in the same container and grown there, or they were first grown separately as seedlings and then transplanted into the test container a few days before treatment. The test plants were kept at either 10–25°C or 20–35°C, depending on the variety. The trial period lasted from two to four weeks. During this time, the test plants were cared for, and their responses to individual treatments were evaluated.

[0309] The evaluation was conducted using a scale from 0 to 100. 100 meant no germination of the test plant or complete destruction of at least the above-ground parts, while 0 meant no damage or normal growth progression. A value of 70 to <90 was considered high herbicidal activity, and a value of 90 to 100 was considered very high herbicidal activity.

[0310] The test plant species used in the greenhouse experiment are as follows:

[0311] [Table 56]

[0312] The fertilizer was applied using the post-germination method at an application rate of 0.063 kg / ha: Compound I.49 showed good herbicidal activity against ALOMY. Compound I.61 showed very good herbicidal activity against AMARE. Compound I.49 showed good herbicidal activity against AVEFA. Compound I.61 showed good herbicidal activity against CHEAL. Compound I.61 showed very good herbicidal activity against ECHCG. Compound I.49 showed good herbicidal activity against LOLMU.

[0313] The fertilizer was applied using the pre-germination method at an application rate of 0.125 kg / ha: Compound I.62 showed good herbicidal activity against ECHCG. Compound I.62 showed very good herbicidal activity against SETFA.

[0314] The fertilizer was applied using the post-germination method at an application rate of 0.125 kg / ha: Compound I.62 showed very good herbicidal activity against AMARE. Compounds I.238 and I.248 showed good herbicidal activity against AMARE. Compound I.60 showed very good herbicidal activity against AVEFA. Compound I.62 showed very good herbicidal activity against CHEAL. Compounds I.62 and I.243 showed very good herbicidal activity against ECHCG. Compound I.60 showed very good herbicidal activity against LOLMU. Compound I.60 showed very good herbicidal activity against POLCO.

[0315] The fertilizer was applied using the pre-germination method at an application rate of 0.250 kg / ha: Compounds I.3, I.23, I.242, I.245, I.247, and I.256 showed high herbicidal activity against AMARE. Compounds I.255 and I.258 showed very good herbicidal activity against AMARE. Compounds I.4, I.5, I.106, and I.256 showed very good herbicidal activity against DIGSA. Compound I.22 showed good herbicidal activity against DIGSA. Compound I.2 showed good herbicidal activity against LOLMU. Compounds I.3, I.4, I.5, I.22, I.24, I.101, I.103, and I.106 showed very good herbicidal activity against LOLMU. Compounds I.3, I.4, I.5, I.22, I.101, and I.103 showed very high herbicidal activity against SETVI. Compounds I.23 and I.106 showed good herbicidal activity against SETVI.

[0316] The fertilizer was applied using the post-germination method at an application rate of 0.250 kg / ha: Compounds I.24, I.28, I.101, I.182, I.213, I.254, I.257, and I.259 showed very good herbicidal activity against ALOMY. Compounds I.7, I.21, I.22, I.23, I.26, I.27, I.54, I.188, and I.239 showed good herbicidal activity against ALOMY. Compounds I.2, I.3, I.4, I.5, I.64, I.65, I.103, I.106, I.241, and I.257 showed very high herbicidal activity against AMARE. Compounds I.42, I.213, I.256, and I.259 showed good herbicidal activity against AMARE. Compounds I.2, I.3, I.4, I.5, I.7, I.21, I.22, I.23, I.24, I.28, I.53, I.54, I.64, I.65, I.101, I.103, I.106, I.182, I.213, I.256, and I.259 showed very high herbicidal activity against AVEFA. Compounds I.26, I.27, I.34, I.42, I.183, I.239, I.240, and I.254 showed good herbicidal activity against AVEFA. Compounds I.2, I.3, I.4, I.5, I.7, I.21, I.22, I.24, I.26, I.28, I.64, I.65, I.101, I.103, I.106, I.182, and I.257 showed very good herbicidal activity against ECHCG. Compounds I.23, I.34, I.42, I.54; I.188, and I.254 showed very good herbicidal activity against ECHCG. Compound I.53 showed good herbicidal activity against LOLMU.

[0317] Comparative evaluation of the herbicidal activity of compounds according to the present invention compared to compounds disclosed in International Publication No. 2023 / 025854:

[0318] The herbicidal activity of the compound was demonstrated according to the same greenhouse experimental procedure described above in this specification.

[0319] [Table 57]

[0320] [Table 58]

Claims

1. Equation (I) 【Chemistry 1】 [In the formula, the substituents have the following meanings: R １ 、 R ８ are, independently of each other, hydrogen, (C １ - C ３ ) - alkyl, (C １ - C ３ ) - haloalkyl, (C ３ - C ４ ) - cycloalkyl, (C ２ - C ３ ) - alkenyl, (C ２ - C ３ ) - haloalkenyl, (C ３ - C ４ ) - alkynyl, (C ３ - C ４ ) - haloalkynyl, (C １ ) - alkoxy - (C ３ - C １ - C ３ ) - alkyl, aryl, aryl - (C １ - C ３ ) - alkyl, (C １ - C ３ ) - alkoxy, (C １ - C ３ ) - haloalkoxy, (C １ - C ３ ) - alkoxy - (C １ - C ３ ) - alkoxy, (C １ - C ３ ) - alkylcarbonyl, arylcarbonyl, (C １ - C ３ ) - alkoxycarbonyl, or aryloxycarbonyl; R ２ , R ６ These are, independently of each other, hydrogen, halogen, hydroxyl, cyano, (C １ ~C ３ )-alkyl, (C １ ~C ３ )-Haloalkyl, (C １ ~C ３ )-alkoxy, or (C １ ~C ３ ) - It is a haloalkoxy; R ３ , R ５ These are, independently of each other, hydrogen, halogen, nitro, hydroxyl, cyano, (C １ ~C ３ )-alkyl, (C １ ~C ３ )-Haloalkyl, (C ３ ~C ５ )-cycloalkyl, (C ３ ~C ５ )-Halocycloalkyl, (C ２ ~C ３ ) - Alkenil, (C ２ ~C ３ ) - Haloalkenyl, (C ２ ~C ３ )-Alkinyl, (C １ ~C ３ )-alkoxy, (C １ ~C ３ )-haloalkoxy, (C １ ~C ３ )-alkoxycarbonyl, (C １ ~C ３ )-haloalkoxycarbonyl, (C １ ~C ３ )-alkylthio, (C １ ~C ３ )-Haloalkylthio, (C １ ~C ３ )-alkylsulfinyl, (C １ ~C ３ )-haloalkylsulfinyl, (C １ ~C ３ )-alkylsulfonyl, (C １ ~C ３ )-haloalkylsulfonyl, or (C １ ~C ３ ) - dialkylamino; R ４ is hydrogen, halogen, hydroxyl, cyano, (C １ ~C ３ )-alkyl, (C １ ~C ３ )-haloalkyl, (C ３ ~C ４ )-cycloalkyl, (C ３ ~C ４ )-halocycloalkyl, (C １ ~C ３ )-alkoxy, (C １ ~C ３ )-haloalkoxy, (C ２ ~C ３ )-alkenyl, (C ２ ~C ３ )-haloalkenyl, (C ２ ~C ３ )-alkynyl, (C １ ~C ３ )-dialkylamino, or (C １ ~C ３ )-alkylthio; R ７ is methyl or ethyl; R ９ is hydrogen; X is oxygen or sulfur; Q is the equation (Z - Y) 【Chemistry 2】 (In the formula, arrows represent bonds to adjacent nitrogen atoms, and substituents have the following meanings) R １０ is, (C １ ~C ４ ) - Alkyl; R １１ , R １２ , R １３ , R １４ These are, independently of each other, hydrogen or (C １ ~C ４ ) - Alkyl; or R １０ and R １４ Together with the carbon atoms to which they are bonded, they form a 3- to 6-membered saturated or partially unsaturated carbon ring or a 3- to 6-membered saturated or partially unsaturated heterocycle containing one or two oxygen, nitrogen, or sulfur atoms as ring members. Y is CO ２ R ｅ CONR ｂ R ｈ CONR ｅ S(O)R ａ CONR ｅ SO ２ R ａ , or CONR ｂ１ SO ２ NR ｂ２ R ｂ３ And; Each R ａ (C １ ~C ６ )-alkyl, (C １ ~C ６ )-Haloalkyl, (C ３ ~C ４ )-Alkinyl, or (C ３ ~C ６ )-cycloalkyl, each of which is fluorine, chlorine, bromine, iodine, cyano, hydroxy, and (C １ ~C ３ ) Substituted with m groups selected from the group consisting of alkoxys; R ｂ is hydrogen, or (C １ ~C ６ )-alkyl, (C ２ ~C ４ ) - Alkenil, (C ３ ~C ４ )-Alkinyl, (C ３ ~C ６ )-cycloalkyl, (C ３ ~C ６ )-cycloalkyl-(C １ ~C ３ )-alkyl,phenyl-(C １ ~C ３ )-alkyl, or furanyl-(C １ ~C ３ ) - Alkyl, where each of the last seven groups listed is fluorine, chlorine, bromine, cyano, CO ２ R ａ , (C １ ~C ２ )-alkoxy, (C １ ~C ３ )-alkylthio, (C １ ~C ３ )-alkylsulfinyl, (C １ ~C ３ ) is substituted with m groups selected from the group consisting of alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; R ｂ１ and R ｂ２ These are, independently of each other and independently of each occurrence, hydrogen or R ａ It has one of the meanings indicated in relation to, R ｂ３ is hydrogen, or (C １ ~C ６ )-alkyl, (C ２ ~C ４ ) - Alkenil, (C ３ ~C ４ )-Alkinyl, (C ３ ~C ６ )-cycloalkyl, (C ３ ~C ６ )-cycloalkyl-(C １ ~C ３ )-alkyl,phenyl-(C １ ~C ３ )-alkyl, or furanyl-(C １ ~C ３ ) - Alkyl, where each of the last seven groups listed is fluorine, chlorine, bromine, cyano, CO ２ R ａ , (C １ ~C ２ )-alkoxy, (C １ ~C ３ )-alkylthio, (C １ ~C ３ )-alkylsulfinyl, (C １ ~C ３ ) - Substituted with m groups selected from the group consisting of alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; or R ｂ２ and R ｂ３ Together with the nitrogen atoms to which they are bonded, they form ring members N, O, S, S(O), and S(O). ２ Forming a saturated 3, 4, 5, 6, or 7-membered N-bonded heterocycle that may contain one further heteroatom or heteroatomic group selected from the group consisting of; Each R ｅ Independently, hydrogen, or (C １ ~C ６ )-alkyl, (C ２ ~C ４ ) - Alkenil, (C ２ ~C ４ )-Alkinyl, (C ３ ~C ６ )-cycloalkyl, (C ３ ~C ６ )-cycloalkyl-(C １ ~C ３ )-alkyl,phenyl-(C １ ~C ３ )-alkyl, or furanyl-(C １ ~C ３ ) - Alkyl, where each of the last seven groups listed is fluorine, chlorine, bromine, cyano, CO ２ R ａ , (C １ ~C ２ )-alkoxy, (C １ ~C ２ )-haloalkoxy, (C １ ~C ３ )-alkylthio, (C １ ~C ３ )-Haloalkylthio, (C １ ~C ３ )-alkylsulfinyl, (C １ ~C ３ )-haloalkylsulfinyl, (C １ ~C ３ )-alkylsulfonyl, (C １ ~C ３ ) - Substituted with m groups selected from the group consisting of haloalkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; R ｈ is hydrogen, or (C １ ~C ６ )-alkyl, (C １ ~C ２ )-alkoxy, (C ３ ~C ６ )-cycloalkyl, (C ２ ~C ４ ) - Alkenil, (C １ ~C ６ )-alkoxycarbonyl-(C １ ~C ６ )-alkyl, or (C ３ ~C ４ ) - Alkynyl, where each of the last six groups listed is fluorine, chlorine, bromine, cyano, CO ２ R ａ , (C １ ~C ２ )-alkyl, (C １ ~C ２ )-alkoxy, and (C １ ~C ２ )-alkoxy-(C １ ~C ２ ) Substituted with m groups selected from the group consisting of alkoxys; or R ｂ and R ｈ Together with the nitrogen atoms to which they are bonded, they form ring members N, O, S, S(O), and S(O). ２ Forming a saturated 3, 4, 5, 6, or 7-membered N-bonded heterocycle that may contain one further heteroatom or heteroatomic group selected from the group consisting of; m is independently 0, 1, 2, or 3 in each occurrence; n is either 1 or 2. Compounds comprising the compounds, their agriculturally acceptable salts, stereoisomers and tautomers; except for the following compounds: (1R,3S)-3-[[2-[(3-nitrobenzoyl)amino]-1-oxopropyl]amino]cyclopentanecarboxylic acid, (1R,3S)-3-[[2-[(2,3-dichlorobenzoyl)amino]-1-oxopropyl]amino]cyclopentanecarboxylic acid, (1S,3R)-3-[[2-[(3-nitrobenzoyl)amino]-1-oxopropyl]amino]cyclopentanecarboxylic acid, (1S,3R)-3-[[2-[(2,3-dichlorobenzoyl)amino]-1-oxopropyl]amino]cyclopentanecarboxylic acid, 3-[[2-(benzoylamino)-1-oxopropyl]amino]cyclopentanecarboxylic acid, 3-[[2-[(2,3-dichlorobenzoyl)amino]-1-oxopropyl]amino]cyclopentanecarboxylic acid, 3-[[2-[(4-bromobenzoyl)amino]-1-oxopropyl]amino]cyclopentanecarboxylic acid, 4-[[2-(benzoylamino)-1-oxopropyl]amino]cyclohexanecarboxylic acid, 4-[[2-(benzoylamino)-1-oxopropyl]aminopentanoic acid, 4-[[2-[(2,3-dichlorobenzoyl)amino]-1-oxopropyl]amino]cyclohexanecarboxylic acid, 4-[[2-[(2,3-dichlorobenzoyl)amino]-1-oxopropyl]aminopentanoic acid, 4-[[2-[(2-chlorobenzoyl)amino]-1-oxopropyl]amino]cyclohexanecarboxylic acid, 4-[[2-[(3-nitrobenzoyl)amino]-1-oxopropyl]amino]cyclohexanecarboxylic acid, 4-[[2-[(3-nitrobenzoyl)amino]-1-oxopropyl]amino]pentanoic acid, 4-[[2-[(4-bromobenzoyl)amino]-1-oxopropyl]amino]cyclohexanecarboxylic acid, 4-[[2-[(4-bromobenzoyl)amino]-1-oxopropyl]aminopentanoic acid, 4-[[2-[(4-chlorobenzoyl)amino]-1-oxopropyl]amino]cyclohexanecarboxylic acid, 4-[[2-[[4-(1,1-dimethylethyl)benzoyl]amino]-1-oxopropyl]amino]cyclohexanecarboxylic acid, cis-3-[[2-[(2,3-dichlorobenzoyl)amino]-1-oxopropyl]amino]cyclobutanecarboxylic acid, cis-3-[[2-[(3-nitrobenzoyl)amino]-1-oxopropyl]amino]cyclobutanecarboxylic acid N-[1-methyl-2-oxo-2-[[(1S,3R)-3-(1-piperidinylcarbonyl)cyclopentyl]amino]ethyl]benzamide.

2. R １ is hydrogen; R ８ The compound according to claim 1, wherein is hydrogen.

3. R ２ is hydrogen or halogen; R ６ is hydrogen, preferably R ２ is hydrogen, and R ６ The compound according to claim 1 or 2, wherein is hydrogen.

4. R ３ is hydrogen, halogen, (C １ ~C ３ )-alkyl, (C １ ~C ３ )-Haloalkyl, (C １ ~C ３ )-alkoxy, or (C １ ~C ３ ) - It is a haloalkoxy; R ５ is hydrogen, halogen, (C １ ~C ３ )-alkyl, (C １ ~C ３ )-Haloalkyl, (C １ ~C ３ )-alkoxy, or (C １ ~C ３ ) - Haloalkoxy; preferably, R ３ and R ５ The compound according to any one of claims 1 to 3, wherein each is independently hydrogen or halogen.

5. R ４ The compound according to any one of claims 1 to 4, wherein is hydrogen or a halogen; more preferably hydrogen.

6. R ７ The compound according to any one of claims 1 to 5, wherein is methyl.

7. R １０ The compound according to any one of claims 1 to 6, wherein is methyl.

8. The compound according to any one of claims 1 to 7, wherein X is oxygen.

9. Q is Z １ -Y to Z ８ - Group Y: 【Transformation 3】 [In the formula, Y is CO ２ R ｅ And, R ｅ is hydrogen, (C １ ~C ６ )-alkyl, or (C ３ ~C ６ The compound according to any one of claims 1 to 8, wherein Z-Y is selected from )-cycloalkyl.

10. Formula (I.R) [wherein, R １ ~R ８ A compound of [X and Q as defined in any one of claims 1 to 9] wherein the stereocenter (#) is in an R configuration. 【Chemistry 4】

11. R １ is hydrogen; R ２ is hydrogen or halogen; R ３ It is a halogen; R ４ is hydrogen or halogen; R ５ is hydrogen or halogen; R ６ is hydrogen; R ７ is methyl or ethyl; R ８ is hydrogen; X is oxygen; Q is the equation (Z - Y) 【Transformation 5】 [In the formula, arrows represent bonds to adjacent nitrogen atoms, and substituents have the following meanings] R １０ It is methyl; R １１ , R １２ , R １３ , R １４ is hydrogen; or R １０ and R １４ Together with the carbon atoms to which they are bonded, they form a 4- to 6-membered saturated or partially unsaturated carbon ring or a 5-membered partially unsaturated heterocycle containing one oxygen atom as a ring member; Y is CO ２ R ｅ And, R ｅ is hydrogen, or (C １ ~C ６ )-alkyl or (C ３ ~C ６ ) - Cycloalkyl, where each of the last two groups listed is (C １ ~C ２ )-alkoxy, (C １ ~C ３ )-alkylthio, (C １ ~C ３ )-alkylsulfinyl, (C １ ~C ３ ) is substituted with m groups selected from the group consisting of alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl; m is 0, 1, or 2; The compound according to claim 10, wherein n represents a group of 1.

12. A composition comprising at least one compound of formula (I) as described in any one of claims 1 to 11, and at least one adjutant commonly used to formulate crop protection compounds.

13. Use of a compound of formula (I) according to any one of claims 1 to 11 or a composition according to claim 12 for controlling undesirable vegetation.

14. A method for controlling undesirable vegetation, comprising applying an effective amount of at least one compound of formula (I) described in any one of claims 1 to 11, or the composition described in claim 12, to a plant, its seeds and / or its habitat.

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