Novel substituted bicyclic pyridine carboxamide compounds for combating phytopathogenic fungi

Abstract

The present invention relates to novel substituted fused bicyclic pyridine carboxamide compounds for combating phytopathogenic fungi. 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , X, Z1 and Z2 are as defined in the Detailed Description, and methods for making compounds of formula (I). The present invention also provides compositions and combinations comprising the novel fused bicyclic pyridine carboxamide compounds, and methods of controlling phytopathogenic fungi therewith. [Formula 1] TIFF2024546982000063.tif2256 formula (I)

Description

[Technical field]

[0001] The present invention relates to novel fused bicyclic pyridinecarboxamide compounds useful for controlling phytopathogenic fungi, and to methods for making the novel fused bicyclic pyridinecarboxamide compounds. The present invention also relates to compositions and combinations comprising the fused bicyclic pyridinecarboxamide compounds, and methods for controlling phytopathogenic fungi using the same. [Background technology]

[0002] Fused bicyclic pyridinecarboxamide compounds have been described as fungicides in WO 2004039783, WO 2018172133, WO 2017153380, WO 2019053010 and WO 2021063736. The fused bicyclic pyridinecarboxamide compounds reported in the above cited documents have drawbacks in certain aspects, such as a narrow spectrum of efficacy or insufficient fungicidal activity, especially at low application rates.

[0003] Thus, there remains a need to develop new fungicidal compounds, including those belonging to the class of fused bicyclic pyridine carboxamide compounds cited above, to provide compounds that are effective against a broader spectrum of fungi, have lower toxicity, greater selectivity, and can be used at lower dosage rates to reduce or avoid undesirable environmental or toxicological effects.

[0004] It is therefore an object of the present invention to provide compounds with improved / enhanced activity and / or a broader spectrum of effectiveness against phytopathogenic fungi.

[0005] This object is achieved by the use of the compounds according to the invention for combating plant pathogens. Summary of the Invention

[0006] The present invention provides a compound of formula (I): [ka] Formula (I) In the formula, R 1 , R 2 , R 3 , R 5、 R 6 , R 7 , R 8 , R 9 , R 11 , X, Z1 and Z2 are as defined in the detailed description.

[0007] The present invention also relates to a process for the preparation of the compounds of formula (I).

[0008] The compounds of formula (I) have been found to be advantageous over compounds reported in the literature, either in improved fungicidal activity, a broader spectrum of biological effectiveness, lower application rates, more favorable biological and environmental properties, or enhanced plant compatibility.

[0009] The present invention further relates to an agrochemical composition comprising a compound of formula (I) or a compound of formula (I) in combination with one or more further insecticidal active substances, in particular for controlling and / or preventing plant diseases caused by phytopathogenic fungi.

[0010] The present invention further relates to a method for controlling or preventing the attack of useful plants by phytopathogenic microorganisms, comprising applying to the plant, a part thereof, or the locus thereof a fungicidally effective amount of a compound of formula (I), a composition, or a combination thereof. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] Definition: The definitions provided herein for terms used in this disclosure are for illustrative purposes only and are not intended to limit the scope of the inventions disclosed in this disclosure.

[0012] As used herein, the terms "comprise," "include," "including," "containing," "having," "having," "containing," "characterized by," or other variations thereof, cover a non-exclusive inclusion, subject to any expressly stated limitations that are intended. For example, a composition, mixture, method or process that includes a list of elements is not necessarily limited to only those elements, but can include other elements not expressly listed or inherent to such composition, mixture, method or process.

[0013] The transitional phrase "consisting of" excludes any element, step, or ingredient not specified. When recited in a claim, such a phrase closes the claim to include materials other than those recited, except for impurities ordinarily associated therewith. When the phrase "consisting of" appears in a clause in the body of the claim rather than immediately following the preamble, it limits only the elements recited in that clause. Other elements are not excluded from the claim as a whole.

[0014] Furthermore, unless expressly stated to the contrary, "or" refers to an inclusive "or" rather than an exclusive "or." For example, a condition A "or" B is satisfied by one of the following: A is true (or exists) and B is false (or does not exist), A is false (or does not exist) and B is true (or exists), or both A and B are true (or exist).

[0015] Also, the indefinite articles "a" and "an" preceding an element or component of the invention are open-ended with respect to the number of instances (i.e., occurrences) of the element or component. Thus, "a" or "an" should be interpreted as including one or at least one, and singular word forms of the element or component also include the plural, unless the number is clearly intended to be singular.

[0016] The term "invertebrate pests" referred to in this disclosure includes, but is not limited to, fungi, stramenopiles (oomycetes), bacteria, nematodes, mites, mites, insects and economically important nematodes.

[0017] In the context of this disclosure, "pest control" means inhibition of development (including necrosis, growth retardation and / or death) of invertebrate pests, and related expressions are similarly defined.

[0018] The term "agricultural" refers to the production of field crops, such as for food, feed and fiber, and includes the growing of corn, soybeans and other legumes, rice, grains (e.g., wheat, oats, barley, rye, rice, corn), leafy vegetables (e.g., lettuce, cabbage, and other cole crops), fruiting vegetables (e.g., tomatoes, peppers, eggplant, rapeseed, melons), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pomegranates, stonecrops, citrus), small fruits (berries, cherries) and other specialty crops (e.g., canola, sunflowers, olives).

[0019] The term "non-agricultural" refers to uses other than field crops, such as horticultural crops (e.g., greenhouse plants, nursery plants, ornamental plants not grown outdoors), residential, agricultural, commercial and industrial structures, turf (e.g., turf farms, pastures, golf courses, lawns, sports fields, etc.), timber products, storage products, agroforestry and vegetation management, public health (i.e., humans) and animal health (e.g., domestic animals such as pets, livestock, poultry, and non-domestic animals such as wildlife) uses.

[0020] Non-agricultural uses include protecting animals from fungal disease by administering a fungicidally effective (i.e. biologically effective) amount of the compounds of the present invention, typically in the form of a veterinary formulated composition, to the animal to be protected. As referred to in this disclosure and claims, the terms "fungicidal" and "fungicidal" refer to an observable effect against fungal pathogens, protecting the animal from disease. A fungicidal effect typically relates to reducing the occurrence or activity of the target pathogen. Such effects on pathogens include necrosis, death, growth retardation, or reduced growth potential on or within the host animal. These effects on pathogens provide control (including prevention, reduction, or elimination) of infestation or infection in animals.

[0021] Here, the meaning of various terms used in the specification will be explained.

[0022] The term "alkyl", when used alone or in compound words such as "alkylthio" or "haloalkyl" or -N(alkyl) or alkylcarbonylalkyl, means a straight or branched C1-C 24 Alkyl, preferably C1-C 15 Alkyl, more preferably C1-C 10Including alkyl, most preferably C1-C6 alkyl. Non-limiting examples of alkyl include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 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 or different isomers. When alkyl is at the terminal of a compound substituent, the terminal portion of the compound substituent, e.g., cycloalkyl, may be independently mono- or polysubstituted with alkyl, either the same or different, such as alkylcycloalkyl. The same applies to compound substituents terminated with other radicals, e.g., alkenyl, alkynyl, hydroxy, halogen, carbonyl, carbonyloxy, etc.

[0023] The term "alkenyl", used alone or in compound words, means any straight or branched C-C 24 Alkenes, preferably C2-C 15 Alkenes, more preferably C2-C 10Alkenes include, most preferably, C2-C6 alkenes. Non-limiting examples of alkenes include 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, 1,2-di, 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, 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-3,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3, Examples include 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 and different isomers."Alkenyl" also includes polyenes, such as 1,2-propadienyl and 2,4-hexadienyl. This definition also applies to alkenyl as part of a compound substituent, such as haloalkenyl, unless specifically defined elsewhere.

[0024] Non-limiting examples of alkynes include ethynyl, 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-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, Examples of alkynyl include 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-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 and various isomers. This definition also applies to alkynyl as part of a compound substituent, such as haloalkynyl, unless otherwise specifically defined. The term "alkynyl" can also include moieties consisting of multiple triple bonds, such as 2,5-hexadiynyl.

[0025] The term "cycloalkyl" refers to an alkyl closed to form a ring. Non-limiting examples include cyclopropyl, cyclopentyl, and cyclohexyl. This definition also applies to cycloalkyl as part of a compound substituent, such as cycloalkylalkyl, unless otherwise specifically defined.

[0026] The term "cycloalkenyl" refers to an alkenyl that is closed to form a ring containing a monocyclic partially unsaturated hydrocarbyl group. Non-limiting examples include cyclopropenyl, cyclopentenyl and cyclohexenyl. This definition also applies to cycloalkenyl as part of a compound substituent, such as cycloalkenylalkyl, unless otherwise specified.

[0027] The term "cycloalkynyl" refers to an alkynyl that is closed to form a ring, including a monocyclic partially unsaturated group. Non-limiting examples include cyclopropynyl, cyclopentynyl, and cyclohexynyl. This definition also applies to cycloalkynyl as part of a compound substituent, such as cycloalkynylalkyl, unless otherwise specified.

[0028] Terms such as "cycloalkoxy", "cycloalkenyloxy" are similarly defined. Non-limiting examples of cycloalkoxy include cyclopropyloxy, cyclopentyloxy, and cyclohexyloxy. This definition also applies to cycloalkoxy as part of a compound substituent, such as cycloalkoxyalkyl, unless otherwise specifically defined.

[0029] The term "halogen", alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine. Furthermore, when used in compound words such as "haloalkyl", said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Non-limiting examples of "haloalkyl" include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1,1-dichloro-2,2,2-trifluoroethyl, and 1,1,1-trifluoroprop-2-yl. This definition also applies to haloalkyl as part of a composite substituent, such as haloalkylaminoalkyl, unless otherwise defined.

[0030] The terms "haloalkenyl" and "haloalkynyl" are similarly defined except that instead of an alkyl group, an alkenyl group and an alkynyl group are present as part of the substituent.

[0031] The term "haloalkoxy" refers to a straight-chain or branched alkoxy group, in which some or all of the hydrogen atoms of the group may be replaced with halogen atoms as described above.Non-limiting examples of haloalkoxy include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 1,1,1-trifluoroprop-2-oxy. This definition also applies to haloalkoxy, such as haloalkoxyalkyl, as part of a compound substituent, unless otherwise defined.

[0032] The term "haloalkylthio" refers to a straight-chain or branched alkylthio group, and some or all of the hydrogen atoms of these groups may be replaced with the above-mentioned halogen atoms.Non-limiting examples of haloalkylthio include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 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, pentafluoroethylthio and 1,1,1-trifluoroprop-2-ylthio.This definition also applies to haloalkylthio as part of a compound substituent such as haloalkylthioalkyl, unless otherwise defined.

[0033] Non-limiting examples of "haloalkylsulfinyl" include CF3S(O), CCl3S(O), CF3CH2S(O) and CF3CF2S(O). Non-limiting examples of "haloalkylsulfonyl" include CF3S(O). 2、 CCl3S(O) 2、 Examples include CF3CH2S(O)2 and CF3CF2S(O)2.

[0034] The term "hydroxy" means -OH, "cyano" means -CN, and "amino" means -NRR, where R can be any possible substituent such as H or alkyl. Carbonyl means -C(=O)-, carbonyloxy means -OC(=O)-, sulfinyl means SO, and sulfonyl means S(O).

[0035] The term "oxo" as used herein, alone or in combination, refers to =O.

[0036] The term "alkoxy", used alone or in compound words, means C1-C 24 Alkoxy, preferably C1-C 15 Alkoxy, more preferably C1-C 10Alkoxy, most preferably C1 to C6 alkoxy. Examples of alkoxy include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpent ... It includes pentoxy, 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 and 1-ethyl-2-methylpropoxy, as well as their different isomeric forms. This definition also applies to alkoxy as part of a compound substituent, such as haloalkoxy, alkenylalkoxy, alkynylalkoxy, etc., unless otherwise specifically defined.

[0037] The term "alkenyloxy," as used herein, refers to an alkenyl group, as defined herein, appended to the parent molecular moiety through an oxy group, as defined herein.

[0038] The term "alkynyloxy," as used herein, refers to an alkynyl group appended to the parent molecular moiety through an oxy group.

[0039] The term "alkoxyalkyl" denotes an alkoxy substitution on an alkyl. Non-limiting examples of "alkoxyalkyl" include CH3OCH2, CH3OCH2CH2, CH3CH2OCH2, CH3CH2CH2CH2OCH2 and CH3CH2OCH2CH2.

[0040] The term "alkoxyalkoxy" denotes an alkoxy substitution on an alkoxy.

[0041] The term "alkylthio" refers to a branched or straight chain alkylthio moiety, such as, for example, methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpropyl ... These include ethylpentylthio, 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, 1-ethyl-2-methylpropylthio and the various isomers.

[0042] Halocycloalkyl, halocycloalkenyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylcarbonyl, cycloalkylcarbonyl, haloalkoxylalkyl, and the like are defined as in the above examples.

[0043] The term "alkylthioalkyl" denotes alkylthio substitution on alkyl. Non-limiting examples of "alkylthioalkyl" include -CH2SCH2, -CH2SCH2CH2, CH3CH2SCH2, CH3CH2CH2SCH2 and CH3CH2SCH2CH2. The term "alkylthioalkoxy" denotes alkylthio substitution on alkoxy. The term "cycloalkylalkylamino" denotes cycloalkyl substitution on alkylamino.

[0044] The terms "alkoxyalkoxyalkyl", "alkylaminoalkyl", "dialkylaminoalkyl", "cycloalkylaminoalkyl", "cycloalkylaminocarbonyl", and the like are defined analogously as "alkylthioalkyl" or "cycloalkylalkylamino".

[0045] The term "alkoxycarbonyl" refers to an alkoxy group attached to the backbone via a carbonyl group (-CO-). This definition also applies to alkoxycarbonyl as part of a compound substituent, such as cycloalkylalkoxycarbonyl, unless otherwise specifically defined.

[0046] The term "alkoxycarbonylalkylamino" denotes an alkoxycarbonyl substitution on an alkylamino. "Alkylcarbonylalkylamino" denotes an alkylcarbonyl substitution on an alkylamino. The terms alkylthioalkoxycarbonyl, cycloalkylalkylaminoalkyl, etc. are similarly defined.

[0047] Non-limiting examples of "alkylsulfinyl" include methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, The term "arylsulfinyl" includes 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 and 1-ethyl-2-methylpropylsulfinyl, as well as different isomers. The term "arylsulfinyl" includes Ar-S(O), where Ar can be any carbocyclic or heterocyclic ring. This definition also applies to alkylsulfinyl, such as haloalkylsulfinyl, as part of a compound substituent, unless otherwise specified.

[0048] Non-limiting examples of "alkylsulfonyl" include methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, These include 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 and 1-ethyl-2-methylpropylsulfonyl and different isomers. The term "arylsulfonyl" includes Ar-S(O)2, where Ar can be any carbocyclic or heterocyclic ring. This definition also applies to alkylsulfonyl as part of a compound substituent, such as alkylsulfonylalkyl, unless otherwise defined.

[0049] "Alkylamino", "dialkylamino", etc. are defined as in the above examples. The term "carbocyclic or carbocyclic" includes "aromatic carbocyclic ring systems" and "non-aromatic carbocyclic ring systems", or polycyclic or bicyclic (spiro, fused, bridged, non-fused) ring compounds in which the rings may be aromatic or non-aromatic (where aromatic indicates that Huckel's rule is satisfied and non-aromatic indicates that Huckel's rule is not satisfied).

[0050] The term "heterocycle or heterocyclic ring" includes (spiro, fused, bridged, non-fused) and "non-aromatic heterocyclic ring systems", or polycyclic or bicyclic compounds in which the rings may be aromatic or non-aromatic, where a heterocycle is any of N, O, S(O), 0~2 and / or the C-ring members of the heterocycle may be replaced by C(=O), C(=S), C(=CR*R*) and C=NR*, where * indicates an integer. The term "heterocycloxy" refers to the group heterocycle-O-, in which the heterocycle group is as previously defined.

[0051] The term "non-aromatic heterocycle" or "non-aromatic heterocycle" refers to a 3-15 membered, preferably 3-12 membered, saturated or partially unsaturated heterocycle containing 1-4 heteroatoms from the group oxygen, nitrogen and sulfur: monocyclic, bicyclic or tricyclic heterocycles contain, in addition to the carbocyclic moiety, 1-3 nitrogen atoms and / or 1 oxygen or sulfur atom, or 1-2 oxygen and / or sulfur atoms; if a ring contains multiple oxygen atoms, they are not directly adjacent; non-limiting examples include thietanyl, oxetanyl, oxiranyl, azetidinyl, aziridinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuran ... tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1-pyrazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 1-imidazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-Oxadiazolidin-5-yl, 1,2,4-Thiadiazolidin-3-yl, 1,2,4-Thiadiazolidin-5-yl, 1,2,4-Triazolidin-1-yl, 1,2,4-Triazolidin-3-yl, 1,3,4-Oxadiazolidin-2-yl, 1,3,4-Thiadiazolidin-2-yl, 1,3,4-Triazolidin-1-yl, 1,3,4-Triazolidin-2-yl, 2,3-Dihydrofur-2-yl, 2,3-Dihydrofur-3-yl, 2,4-Dihydrofur-2-yl, 2,4-Dihydrofur-3-yl, 2,3-Dihydrothien-2-yl, 2,3-Dihydrothien-3-yl, 2,4-Dihydrothien-2-yl, 2,4-dihydrothien-3-yl, pyrrolinyl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 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-dihydropyrazol-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, piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, pyrazinyl, morpholinyl, thiomorpholinyl, 1,3-Dioxan-5-yl, 2-Tetrahydropyranyl, 4-Tetrahydropyranyl, 2-Tetrahydrothienyl, 3-Hexahydropyridazinyl, 4-Hexahydropyridazinyl, 2-Hexahydropyrimidinyl, 4-Hexahydropyrimidinyl, 5-Hexahydropyrimidinyl, 2-Piperazinyl, 1,3,5-Hexahydrotriazin-2-yl, 1,2,4-Hexahydrotriazin-3-yl, cycloserine, 2,3,4,5-Tetrahydro[1H]azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl, 3, 4,5,6-tetrahydro[2H]azepin-2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,4,7-tetrahydro[1H]azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl, 2,3,6,7-tetrahydro[1H]azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl, hexahydroazepin-1- or -2- or -3- or -4-yl, tetra- and hexahydrooxepinyl, for example 2,3,4,5-tetrahydro[1 H]oxepin-2- or -3- or -4- or -5- or -6- or -7-yl, This definition also applies to heterocyclyl as part of a compound substituent, such as heterocyclylalkyl, unless otherwise specifically defined. ,

[0052] The term "heteroaryl" or "aromatic heterocycle" refers to a 5- or 6-membered fully unsaturated monocyclic ring system containing 1-4 heteroatoms from the group oxygen, nitrogen and sulfur. If the ring contains one or more oxygen atoms, they are not directly adjacent; a 5-membered heteroaryl group can contain, in addition to carbon atoms, 1-4 nitrogen atoms or 1-3 nitrogen atoms and 1 sulfur or oxygen atom as ring members, non-limiting examples being furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,3,4-triazolyl, tetrazolyl; a nitrogen-linked 5-membered heteroaryl containing 1-4 nitrogen atoms or 1-3 nitrogen atoms. Benzo-fused nitrogen-linked 5-membered heteroaryl containing: the 5-membered heteroaryl group can contain, in addition to carbon atoms, 1-4 nitrogen atoms or 1-3 nitrogen atoms as ring members, where two adjacent carbon ring members or one nitrogen and one adjacent carbon ring member can be bridged by a buta-1,3-diene-1,4-diyl group where one or two carbon atoms can be replaced by nitrogen atoms, where the rings are attached to the backbone through one of the nitrogen ring members, non-limiting examples include 1-pyrrolyl, 1-pyrazolyl, 1,2,4 triazol-1-yl, 1-imidazolyl, 1,2,3 triazol-1-yl and 1,3,4 triazol-1-yl.

[0053] 6-membered heteroaryl containing 1-4 nitrogen atoms: 6-membered heteroaryl groups that may contain, in addition to carbon atoms, 1-3 and 1-4 nitrogen atoms as ring members, respectively, non-limiting examples being 2-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazin-3-yl; benzo-fused 5-membered heteroaryl containing up to 3 nitrogen atoms or 1 nitrogen atom and 1 oxygen or sulfur atom; non-limiting examples include indol-1-yl, indol-2-yl, indol-3-yl, indol-4-yl, indol-5-yl, indol-6-yl, indol-7-yl, benzimidazol-1-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, indazol-1-yl, indazol-2-yl, in ...3-yl, indazol-4-yl, indazol-5-yl, indazol-5-yl, indazol-6-yl, indazol-7-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzothiophen-5-yl, 1-benzothiophen-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzothiophen-5-yl, 1- Benzothiophen-6-yl, 1-benzothiophen-7-yl, 1,3-benzothiazol-2-yl, 1,3-benzothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl, 1,3-benzothiazol-7-yl, 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl and 1,3-benzoxazol-7-yl;Benzo-fused 6-membered heteroaryl containing 1-3 nitrogen atoms: non-limiting examples include quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl, isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl and isoquinolin-8-yl;

[0054] An "aralkyl" or "arylalkyl" is an aryl group linked, as a substituent, through an alkylene group. The alkylene and aryl groups of the aralkyl may be substituted. Examples include, but are not limited to, benzyl, substituted benzyl, 2-phenylethyl, 3-phenylpropyl, and naphthylalkyl. In some cases, the alkylene group is a lower alkylene group.

[0055] The term "aryloxy" as used herein refers to phenoxy, 1-naphthyloxy, 2-naphthyloxy, and the like.

[0056] The term "heteroaryloxy," as used alone or in combination herein, refers to a heteroaryl, as defined herein, bonded to an oxygen atom having a free valence bond from the oxygen atom, such as, for example, pyrrolyloxy, imidazolyloxy, pyrazolyloxy, triazolyloxy, pyrazinyloxy, pyrimidinyloxy, pyridazinyloxy, isothiazolyloxy, isoxazolyloxy, oxazolyloxy, oxadiazolyloxy, thiadiazolyloxy, quinolinyloxy, isoquinolinyloxy, quinazolinyloxy, quinoxalinyloxy, indoloxy, benzimidazolyloxy, benzofuranyloxy, pteridinyloxy, and purinyloxy.

[0057] Non-limiting examples of "alkylcarbonyl" include C(=O)CH3, C(=O)CH2CH2CH3 and C(=O)CH(CH 3)2Non-limiting examples of "alkoxycarbonyl" include CH3OC(=O), CH3CH2OC(=O), CH3CH2CH2OC(=O), (CH 3)2 Non-limiting examples of "alkylaminocarbonyl" include CHNHC(=O), CHCHNHC(=O), CHCHCHNHC(=O), (CH 3)2 Examples of "dialkylaminocarbonyl" include (CH3)2NC(=O), (CH3CH2)2NC(=O), CH3CH2(CH3)NC(=O), CH3CH2CH2(CH3)NC(=O), and (CH3)2CHN(CH3)C(=O). Examples of "alkoxyalkylcarbonyl" include CH3OCH2C(=O), CH3OCH2CH2C(=O), CH3CHOCH2C(=O), CH3CHOCH2CHOCH2C(=O), and CH3CHOCH2CH2C(=O). Non-limiting examples of "alkylthioalkylcarbonyl" include CHSCHC(=O), CHSCHCHC(=O), CHCHSCHC(=O), CHCHCHCHSCHC(=O) and CHCHSCHCHC(=O). The terms "haloalkylsulfonylaminocarbonyl", "alkylsulfonylaminocarbonyl", "alkylthioalkoxycarbonyl", "alkoxycarbonylalkylamino", and the like are similarly defined.

[0058] Non-limiting examples of "alkylaminoalkylcarbonyl" include CH3NHCH2C(=O), CH3NHCH2CH2C(=O), CH3CH2NHCH2C(=O), CH3CH2CH2CH2NHCH2C(=O) and CH3CH2NHCH2CH2C(=O).

[0059] The term "amide" refers to A-R'C=ONR''-B, where R' and R'' represent substituents and A and B represent optional groups.

[0060] The term "thioamide" refers to A-R'C=SNR''-B, where R' and R'' represent substituents and A and B represent optional groups.

[0061] The total number of carbon atoms in a substituent is indicated by the prefix "C i -C j ", where i and j are numbers from 1 to 21. For example, C1-C3 alkylsulfonyl refers to methylsulfonyl through propylsulfonyl. C2 alkoxyalkyl refers to CH3OCH2. C3 alkoxyalkyl refers to, for example, CH3CH(OCH 3) , CH3OCH2CH2 or CH3CHOCH2. C4 alkoxyalkyl refers to various isomers of an alkyl group substituted with an alkoxy group containing a total of 4 carbon atoms. Examples include CH3CH2CH2OCH2 and CH3CHOCH2CH2. In the above description, when the compound of formula (I) contains one or more heterocyclic rings, all substituents are bonded to these rings through any available carbon or nitrogen by replacement of hydrogen on said carbon or nitrogen.

[0062] When a compound is substituted with a substituent having a subscript indicating that the number of substituents may be more than one, the substituents (if more than one) are independently selected from the group of defined substituents. m When the subscript m in (R) represents an integer ranging from 0 to 4, for example, the number of substituents may be selected from integers ranging from 0 to 4. 4 ) where the subscript 1-2 denotes an integer in the range of, for example, 1-2, the number of substituents may be selected from integers in the range of 1-2.

[0063] If a group contains a substituent that can be hydrogen, then the group is recognized as being unsubstituted if the substituent is hydrogen.

[0064] Optionally substituted groups may be mono- or polysubstituted, and if polysubstituted, the substituents may be the same or different.

[0065] The embodiments of the present specification and its various features and advantageous details are described in the description with reference to non-limiting embodiments. Descriptions of well-known components and processing techniques are omitted so as not to unnecessarily obscure the embodiments of the present specification. The examples used in the present specification are merely intended to facilitate the understanding of how the embodiments of the present specification can be implemented and to further enable those skilled in the art to implement the embodiments of the present specification. Therefore, the examples should not be interpreted as limiting the scope of the embodiments of the present specification.

[0066] The description of the specific embodiments will sufficiently clarify the general nature of the embodiments herein, so that others, by applying current knowledge, can easily modify and / or adapt such specific embodiments to various uses without departing from the general concept, and therefore such adaptations and modifications should and are intended to be understood within the meaning and range of equivalents of the disclosed embodiments. It should be understood that the terms used herein are for the purpose of description and not for the purpose of limitation. Thus, although the embodiments herein have been described in terms of preferred embodiments, those skilled in the art will recognize that the embodiments herein can be practiced with modifications within the spirit and scope of the embodiments described herein.

[0067] Any discussion of documents, acts, materials, devices, articles or the like which has been included in the present specification is solely for the purpose of providing a context for the disclosure. No admission is made that any or all of those matters form part of the prior art or were general knowledge in the field relevant to the disclosure existing prior to the priority date of this application.

[0068] While the numerical values ​​set forth in the specification and specification / claims may form an important part of the invention, any departure from such numerical values ​​is intended to be within the scope of the invention, provided that the departure is in accordance with the same scientific principles as those of the invention disclosed herein.

[0069] The compounds of the invention can exist, where appropriate, as mixtures of different possible isomers, in particular stereoisomers, e.g., E and Z, threo and erythro, and optical isomers, but also, where appropriate, as mixtures of tautomers. Both E and Z isomers, as well as threo and erythro isomers, optical isomers, and any mixtures of these isomers and possible tautomers are disclosed and claimed.

[0070] The term "polymorph" refers to a particular crystalline form of a compound that can crystallize in different crystalline forms, these forms having different arrangements and / or conformations of the molecules in the crystal lattice. Polymorphs can have the same chemical composition, but may differ in composition due to the presence or absence of co-crystallized water or other molecules that can bind weakly or strongly in the lattice. Polymorphs can differ in chemical, physical and biological properties such as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspendability, dissolution rate and bioavailability. Those skilled in the art will appreciate that a polymorph of a compound represented by formula (I) can exhibit beneficial effects (e.g., suitability for the preparation of useful formulations, improved biological performance) over another polymorph or mixture of polymorphs of the same compound represented by formula (I). Preparation and isolation of a particular polymorph of a compound represented by formula (I) can be accomplished by methods known to those skilled in the art, including, for example, crystallization using a selected solvent and temperature.

[0071] For purposes of this disclosure, the term "pests" includes, but is not limited to, fungi, stramenopiles (oomycetes), and bacteria.

[0072] The term "plants" is understood herein to mean all plants and plant populations, such as desired and undesired wild or crop plants (including naturally occurring crop plants). Crop plants are plants that can be obtained by conventional breeding and optimization methods, or by biotechnological and genetic engineering methods, or by a combination of these methods, including transgenic plants, and including plant cultivars protectable and non-protectable by plant breeder's rights.

[0073] For purposes of this disclosure, the term "plant" includes the types of organisms exemplified by trees, shrubs, herbs, grasses, ferns, and mosses, which typically grow in a location, absorb water and necessary substances through their roots, and synthesize nutrients in their leaves by photosynthesis.

[0074] Examples of "plants" for the purposes of the present invention include, but are not limited to, crops such as wheat, rye, barley, lima beans, oats or rice; beets, e.g. sugar beet or fodder beet; poms, stone fruits or soft fruits, e.g. apple, pear, plum, peach, almond, cherry, strawberry, raspberry, blackberry or gooseberry; legumes, e.g. lentil, pea, alfalfa or soybean; oilseed rape, mustard, olive, sunflower, coconut, cocoa bean, castor oil plant, oil palm, ground nuts or soybeans; cucurbits, e.g. pumpkin, cucumber, melon; fiber plants, e.g. cotton, flax, hemp, jute; citrus fruits and citrus fruits, e.g. orange, lemon, grapefruit, mandarin orange. Preferably, these include tangerine trees; horticultural plants such as spinach, lettuce, asparagus, cabbage, carrot, onion, tomato, potato, cucurbits, peppers, etc.; laurel plants such as avocado, cinnamon, camphor, etc.; cucurbits; oregano; energy and raw materials plants such as cereals, corn, soybeans, other legumes, rapeseed, sugarcane, oil palm, etc.; tobacco; nuts; coffee; tea; cocoa; bananas; chili peppers; grapes (table grapes and grape juice grapes); hops; grass; sweet leaf (also called stevia); ornamental and forestry plants such as natural rubber plants or flowers, shrubs, broad-leaved or evergreen trees, e.g. conifers; and plant propagation material such as seeds, and crop material of these plants.

[0075] Preferably, plants for the purposes of the present invention include, but are not limited to, cereals, corn, rice, soybeans and other legumes, fruit and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbits, olive plants, tobacco, coffee, tea, cocoa, sugar beet, sugar cane, cotton, potato, tomato, onion, pepper and vegetables, ornamental, any flowering plants and other plants for human and animal use.

[0076] The term "plant parts" is understood to mean all parts and organs of a plant, above and below ground. For the purposes of this disclosure, the term "plant parts" includes, but is not limited to, cuttings, leaves, twigs, tubers, flowers, seeds, branches, roots including the taproot, lateral roots, root hairs, root tips, root caps, rhizomes, slips, shoots, fruits, fruiting bodies, bark, stems, buds, accessory buds, meristems, nodes and internodes.

[0077] The term "locus thereof" includes the soil, the surroundings of the plant or plant part, and any equipment or tools used before, during or after sowing / planting the plant or plant part.

[0078] The terms "pesticidally active agent" and "additional active ingredient" may be used interchangeably.

[0079] Application of the compounds of the present disclosure, or in compositions optionally containing other compatible compounds, to plants, plant materials, or loci thereof includes application by techniques known to those skilled in the art, including, but not limited to, spraying, coating, dipping, fumigating, impregnating, injecting, and dusting.

[0080] The term "applied" means adhered, either physically or chemically, to a plant or plant part, including by impregnation.

[0081] The present invention therefore relates to a compound of formula (I): [ka] Formula (I) In the formula, "----" indicates the presence or absence of a double bond. X is O or S; Z 1 is C(R 4 ) 1-2 , C.H.R. 4 - * CHR 4 , O- * CHR 4 , O, S or N(R 10 ) 0-1where the carbon atom marked with "*" indicates the point of attachment to the carbon atom marked with "#"; Z 2 is C(R 4 ) 1-2 or NR 10 and; however, a) Z 1 S and Z 2 CR 4 In the case of R 5 and R 6 does not form a ring; b) Z 1 is NH and Z 2 is NH and R 3 If is oxo, R 5 and R 6 does not form a ring; c) Z 1 N and Z 2 If N(CH3), then R 5 and R 6 does not form a ring; R 1 is hydrogen, halogen, cyano, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C3-C 10 -cycloalkyl and phenoxy; wherein C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C3-C 10 Cycloalkyl and phenoxy are optionally R 1a may be substituted with one or more groups; R 1ais selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy and C2-C6-alkynyloxy; R 2 is hydrogen, halogen, cyano, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C3-C 10 -cycloalkyl and phenoxy; wherein C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C3-C 10 Cycloalkyl and phenoxy are optionally R 2a may be substituted with one or more groups; R 2a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy and C2-C6-alkynyloxy; R 3 is hydrogen, halogen, oxo, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio and C3-C 10-cycloalkyl; where C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio and C3-C6- 10 -cycloalkyl is optionally R 3a may be substituted with one or more groups; R 3a is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy and C2-C6-alkynyloxy; R 4 is hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio and C3-C 10 -cycloalkyl; where C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio and C3-C6- 10 -cycloalkyl is optionally R 4a may be substituted with one or more groups; R 4a is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy and C2-C6-alkynyloxy; R 5and R 6 are each independently hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylcarbonyl, C1-C6-alkylthio, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl and C6-C 10 -aryl; wherein C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylcarbonyl, C1-C6-alkylthio, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl and C6-C 10 -aryl is optionally R 5a or R 5 and R 6 can form, together with the atoms to which they are attached, a 3- to 6-membered non-aromatic carbocyclic or non-aromatic heterocyclic ring; one or more of the heteroatoms in said ring may be N, O or S(=O) 0-2 one or more C atoms of the ring may be optionally substituted by C(=O), C(=S); the ring may be optionally selected from R 5a may be substituted with one or more of the same or different groups; R 5a is halogen, cyano, nitro, hydroxyl, thiol, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C 10 -cycloalkyl, and C1-C6-alkoxy-C1-C6-alkyl; R 7 and R 8are each independently hydrogen, cyano, halogen, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylcarbonyl and C3-C 10 -cycloalkyl; where C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylcarbonyl and C3-C6- 10 -Cycloalkyl is optionally R 7a or R 7 and R 8 may together with the atoms to which they are attached form a 3- to 6-membered non-aromatic or aromatic carbocyclic or non-aromatic or aromatic heterocyclic ring; one or more of the heteroatoms in said ring may be N, O or S(=O). 0-2 one or more C atoms of the ring may optionally be replaced by C(=O) or C(=S); the ring may optionally be selected from R 7a with one or more identical or different groups; provided that R 7 and R 8 When forms an aromatic ring, R 9 does not exist; R 7a is halogen, cyano, nitro, hydroxyl, thiol, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C 10 -cycloalkyl, and C1-C6-alkoxy-C1-C6-alkyl; R 9 are hydrogen, halogens, C3-C 10 -Cycloalkyl, C3-C 10 -Cycloalkyloxy, C3-C 10 -Cycloalkenyl, C3-C 10 -Cycloalkenyloxy, C6-C 10 -Aryl, C7-C14 -Aralkyl, C6-C 10 -Aryloxy, benzyloxy, -OC(O)-C6-C 10 -Aryl, O-C(O)-C-C 10 -Heterocyclyl, C2-C 10 -Heterocyclyl and C2-C 10 -heterocyclooxy; with the proviso that heterocyclyl or heterocycloxy contains 1, 2 or 3 heteroatoms selected from N, O and S; and in each case 1 or 2 CH2 groups of the carbocycle or heterocycle may be replaced by a group independently selected from C(=O) and C(=S); where C3-C 10 -Cycloalkyl, C3-C 10 -Cycloalkyloxy, C3-C 10 -Cycloalkenyl, C3-C 10 -Cycloalkenyloxy, C6-C 10 -Aryl, C7-C 14 -Aralkyl, C6-C 10 -Aryloxy, benzyloxy, -OC(O)-C6-C 10 -Aryl, O-C(O)-C-C 10 -Heterocyclyl, C2-C 10 -Heterocyclyl and C2-C 10 -heterocycloxy is optionally R 9a or R 5 and R 9 can form, together with the atoms to which they are attached, a 3- to 12-membered non-aromatic carbocyclic or non-aromatic heterocyclic ring; one or more of the heteroatoms in said ring may be N, O or S(=O). 0-2 one or more C atoms of the ring may be optionally substituted by C(=O), C(=S); the ring may be optionally selected from R 9a may be substituted with one or more of the same or different groups; R 9ais hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-C 10 -Cycloalkyl, C(R'')=N-OR', C3-C 10 -Cycloalkyloxy, C3-C 10 -Cycloalkenyl, C3-C 10 -Cycloalkenyloxy, C6-C 10 -Aryl, C7-C 14 -Aralkyl, C6-C 10 -Aryloxy, C2-C 10 -Heterocyclyl and C2-C 10 -heterocyclooxy; R' is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, where each group R' is optionally selected from halogen, cyano, C1-C6-alkoxy, C3-C 10 -Cycloalkyl, C3-C 10 -Cycloalkyloxy, C6-C 10 -Aryl, C7-C 14 -Aralkyl and C6-C 10 -aryloxy; R'' is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C 10 -Cycloalkyl and C-C 10 -cycloalkenyl; R 10 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C 10 -Cycloalkyl and C-C 10 -cycloalkyl-C1-C6-alkyl; R 11 is selected from the group consisting of hydrogen, C1-C6-alkyl and C1-C6-alkoxy; R 1~R 11 , R 1a ~R 5a , R 7a or R 9a Each group is optionally selected from cyano, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C 10 -Cycloalkyl, C3-C 10 -Cycloalkenyl and C6-C 10 -optionally substituted with one or more groups selected from aryl; The present invention provides compounds, or their N-oxides, metal complexes, stereoisomers, polymorphs, or agriculturally acceptable salts thereof. However, the following compounds are excluded from the definition of the compound of formula (I): 2-Methyl-N-(2,4,4,trimethylpentan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(tert-butyl)-2-methyl-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(tert-butyl)-2-methyl-5,6,7,8-tetrahydroquinoline-3-carboxamide 2-Methyl-N-(2,4,4,trimethylpentan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(1-(2-chlorophenoxy)-2-cyanopropan-2-yl)-4-methyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide, N-(2-cyano-1-(5-cyano-2-(trifluoromethyl)phenoxy)propan-2-yl)-4-methyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide, N-(2-(1,2,4-oxadiazol-3-yl)propan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-cyclohexylpropan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, 3-Methyl-N-(1,1,1-trifluoro-2-methylbutan-2-yl)-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-cyclopropyl-1,1,1-trifluoropropan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, 3-Methyl-N-(4,4,4-trifluoro-2-methylbutan-2-yl)-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(4-(azepan-1-yl)-2-methylbutan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-cyclohexyl-1-hydroxypropan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-cyclopropyl-1-hydroxypropan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(1-hydroxy-2-methylbutan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(tert-butyl)-1H-imidazo[4,5-b]pyridine-6-carboxamide, N-(1-(azepan-1-yl)-2-methylpropan-2-yl)-N-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(1-(azepan-1-yl)-2-methylpropan-2-yl)-N-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-(4,5-dimethylthiazol-2-yl)propan-2-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-methyl-4-(4-methylpiperazin-1-yl) butan-2-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-(3,5-dimethylisoxazol-4-yl)propan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-(4,5-dimethylthiazol-2-yl)propan-2-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-6-carboxamide, N-(1-(3-methoxyphenyl)-2-methylpropan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-(tetrahydro-2H-pyran-4-yl)propan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(2-methyl-1-morpholinopropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(2-(1-methyl-1H-1,2,3-triazol-4-yl)propan-2-yl)thieno[3,2-b]pyridine-6-carboxamide.

[0082] In one embodiment, the compound of formula (I) is represented by a compound of formula (IA): [ka] Formula (IA) In the formula, X, Z1, R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 is as defined in the detailed description above.

[0083] In another embodiment, the compound of formula (I) is represented by a compound of formula (IB): [ka] Formula (IB) In the formula, X, Z2, R 1, R 2 , R 3 , R 5 , R 6 , R 7 , R 8、 R 9 and R 11 is as defined in the detailed description above.

[0084] In yet another embodiment, the compound of formula (I) is represented by a compound of formula (IC): [ka] Formula (IC) In the formula, X, Z1, R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 9 and R 11 is as defined in the detailed description above.

[0085] In yet another embodiment, the compound of formula (I) is represented by a compound of formula (ID). [ka] Expression (ID) In the formula, X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 is as defined in the detailed description above.

[0086] In yet another embodiment, the compound of formula (I) is represented by a compound of formula (IE). [ka] Formula (IE) In the formula, X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 11 is as defined in the detailed description above.

[0087] In yet another embodiment, the compound of formula (I) is represented by a compound of formula (IF). [ka] Formula (IF) In the formula, X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 11 is as defined in the detailed description above.

[0088] In yet another embodiment, the compound of formula (I) is represented by a compound of formula (IG). [ka] Expression (IG) In the formula, X, Z2, R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8、 R 9 and R 11 is as defined in the detailed description above.

[0089] In another embodiment, the compound of formula (I): [ka] Formula (I) In the formula, "----" indicates the presence or absence of a double bond. X is O or S; Z 1 is C(R 4 ) 1-2 , C.H.R. 4 - * CHR 4 , O- * CHR 4 , O, S or N(R 10 ) 0-1 where the carbon atom marked with "*" indicates the point of attachment to the carbon atom marked with "#"; Z 2 is C(R 4 ) 1-2 or NR 10 and; however, a) Z 1 S and Z 2 CR 4 In the case of R 5 and R 6 does not form a ring; b) Z 1 is NH and Z 2 is NH and R 3 If is oxo, R 5 and R 6 does not form a ring; c) Z 1 N and Z 2 If N(CH3), then R 5 and R 6 does not form a ring; R 1 is selected from the group consisting of hydrogen, halogen, cyano, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C3-C6-cycloalkyl and phenoxy; 1 Each group is optionally R 1a may be substituted with one or more groups; R1a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy and C2-C6-alkynyloxy; R 2 is selected from the group consisting of hydrogen, halogen, cyano, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio, C3-C6-cycloalkyl and phenoxy; where R 2 Each group is optionally R 2a may be substituted with one or more groups; R 2a is selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy and C2-C6-alkynyloxy; R 3 is selected from the group consisting of hydrogen, halogen, oxo, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio and C3-C6-cycloalkyl; where R 3 Each group is optionally R 3a may be substituted with one or more groups; R 3ais selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy and C2-C6-alkynyloxy; R 4 is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylthio and C3-C6-cycloalkyl; where R 4 Each group is optionally R 4a may be substituted with one or more groups; R 4a is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy and C2-C6-alkynyloxy; R 5 and R 6 are each independently hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-alkylcarbonyl, C1-C6-alkylthio, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl and C6-C 10 -aryl; where R 5 and R 6 Each group is optionally R 5a or R 5 and R 6can form, together with the atoms to which they are attached, a 3- to 6-membered non-aromatic carbocyclic or non-aromatic heterocyclic ring; one or more of the heteroatoms in said ring may be N, O or S(=O) 0-2 one or more C atoms of the ring may be optionally substituted by C(=O), C(=S); the ring may be optionally selected from R 5a may be substituted with one or more of the same or different groups; R 5a is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thiol, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, and C1-C4-alkoxy-C1-C4-alkyl; R 7 and R 8 are each independently selected from the group consisting of hydrogen, cyano, halogen, hydroxy, C-C-alkyl, C-C-haloalkyl, C-C-alkoxy, C-C-alkenyloxy, C-C-alkynyloxy, C-C-alkylcarbonyl and C-C-cycloalkyl; 7 and R 8 Each group may be optionally R 7a or R 7 and R 8 may together with the atoms to which they are attached form a 3- to 6-membered non-aromatic carbocyclic or non-aromatic heterocyclic ring; one or more of the heteroatoms in said ring may be N, O or S(=O). 0-2 one or more C atoms of the ring may optionally be replaced by C(=O) or C(=S); the ring may optionally be selected from R 7a with one or more identical or different groups; provided that R 7 and R 8 When forms an aromatic ring, R 9 does not exist; R 7ais selected from the group consisting of halogen, cyano, nitro, hydroxyl, thiol, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, and C1-C4-alkoxy-C1-C4-alkyl; R 9 are hydrogen, halogens, C3-C 10 -Cycloalkyl, C3-C 10 -Cycloalkyloxy, C3-C 10 -Cycloalkenyl, C3-C 10 -Cycloalkenyloxy, C6-C 10 -Aryl, C7-C 14 -Aralkyl, C6-C 10 -Aryloxy, benzyloxy, -OC(O)-C6-C 10 -Aryl, O-C(O)-C-C 10 -Heterocyclyl, C2-C 10 -Heterocyclyl and C2-C 10 -heterocyclooxy; provided that heterocyclyl or heterocycloxy contains 1, 2 or 3 heteroatoms selected from N, O and S; and in each case, 1 or 2 CH groups of the carbocycle or heterocycle may be replaced by a group independently selected from C(=O) and C(=S); where R 9 Each group is optionally R 9a or R 5 and R 9 can form, together with the atoms to which they are attached, a 3- to 12-membered non-aromatic carbocyclic or non-aromatic heterocyclic ring; one or more of the heteroatoms in said ring may be N, O or S(=O). 0-2 one or more C atoms of the ring may be optionally substituted by C(=O), C(=S); the ring may be optionally selected from R 9a may be substituted with one or more of the same or different groups; R 9ais hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloalkyl, C(R'')=N-OR', C3-C 10 -Cycloalkyloxy, C3-C 10 -Cycloalkenyl, C3-C 10 -Cycloalkenyloxy, C6-C 10 -Aryl, C7-C 14 -Aralkyl, C6-C 10 -Aryloxy, C2-C 10 -Heterocyclyl and C2-C 10 -heterocyclooxy; R' is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, where each group R' is optionally selected from halogen, cyano, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C6-C 10 -Aryl, C7-C 14 -Aralkyl and C6-C 10 -aryloxy; R'' is selected from hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl and C3-C6-cycloalkenyl; R 10 is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C3-C5-cycloalkyl and C3-C5-cycloalkyl-C1-C3-alkyl; R 11 is selected from the group consisting of hydrogen, C1-C4-alkyl and C1-C4-alkoxy; R 1 ~R 11 , R 1a ~R 5a , R 7a or R 9aeach group is optionally selected from cyano, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl and C6-C 10 -optionally substituted with one or more groups selected from aryl; or their N-oxides, metal complexes, stereoisomers, polymorphs or agriculturally acceptable salts thereof. However, the following compounds are excluded from the definition of the compound of formula (I): 2-Methyl-N-(2,4,4,trimethylpentan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(tert-butyl)-2-methyl-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(tert-butyl)-2-methyl-5,6,7,8-tetrahydroquinoline-3-carboxamide 2-Methyl-N-(2,4,4,trimethylpentan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(1-(2-chlorophenoxy)-2-cyanopropan-2-yl)-4-methyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide, N-(2-cyano-1-(5-cyano-2-(trifluoromethyl)phenoxy)propan-2-yl)-4-methyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide, N-(2-(1,2,4-oxadiazol-3-yl)propan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-cyclohexylpropan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, 3-Methyl-N-(1,1,1-trifluoro-2-methylbutan-2-yl)-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-cyclopropyl-1,1,1-trifluoropropan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, 3-Methyl-N-(4,4,4-trifluoro-2-methylbutan-2-yl)-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(4-(azepan-1-yl)-2-methylbutan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-cyclohexyl-1-hydroxypropan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-cyclopropyl-1-hydroxypropan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(1-hydroxy-2-methylbutan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(tert-butyl)-1H-imidazo[4,5-b]pyridine-6-carboxamide, N-(1-(azepan-1-yl)-2-methylpropan-2-yl)-N-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(1-(azepan-1-yl)-2-methylpropan-2-yl)-N-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-(4,5-dimethylthiazol-2-yl)propan-2-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-methyl-4-(4-methylpiperazin-1-yl) butan-2-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-(3,5-dimethylisoxazol-4-yl)propan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-(4,5-dimethylthiazol-2-yl)propan-2-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-6-carboxamide, N-(1-(3-methoxyphenyl)-2-methylpropan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-(tetrahydro-2H-pyran-4-yl)propan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(2-methyl-1-morpholinopropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(2-(1-methyl-1H-1,2,3-triazol-4-yl)propan-2-yl)thieno[3,2-b]pyridine-6-carboxamide.

[0090] In one preferred embodiment, the present invention provides a compound of formula (I), wherein X is O and Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 11 is as defined in the detailed description above.

[0091] In another preferred embodiment, the present invention provides compounds of formula (I), wherein Z 1 CH(R 4 ), and Z 2 NR 10 and X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 11 is as defined in the detailed description above.

[0092] In yet another preferred embodiment, the present invention provides compounds of formula (I), wherein Z 1 is S and Z 2 CHR 4 and X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 11 is as defined in the detailed description above.

[0093] In yet another preferred embodiment, the present invention provides a compound of formula (I), 1 CHR 4 - * CHR 4 where the carbon atom marked with a "*" indicates the point of attachment to the carbon atom marked with a "#", and Z 2 CHR 4 and X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 11 is as defined in the detailed description above.

[0094] In yet another preferred embodiment, the present invention provides a compound of formula (I), 1 CHR 4 and Z 2 CHR 4 and X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 11 is as defined in the detailed description above.

[0095] In yet another preferred embodiment, the present invention provides a compound of formula (I), 1 O- * CHR 4 where the carbon atom marked with a "*" indicates the point of attachment to the carbon atom marked with a "#", and Z 2 NR 10 and X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 11 is as defined in the detailed description above.

[0096] In yet another preferred embodiment, the present invention provides a compound of formula (I), 1 NR 10 and Z 2 CHR 4 and X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 11 is as defined in the detailed description above.

[0097] In yet another preferred embodiment, the present invention provides a compound of formula (I), 1 is O and Z 2 NR 10 and R 3 is oxo, and X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 11is as defined in the detailed description above.

[0098] In one embodiment, the compound of formula (I) comprises X is O; R 1 is selected from the group consisting of hydrogen, halogen, cyano, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl and C1-C6-alkoxy; R 2 is selected from the group consisting of hydrogen, halogen, cyano, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylthio and C3-C6-cycloalkyl; R 3 is selected from the group consisting of hydrogen, halogen, oxo, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylthio and C3-C6-cycloalkyl; R 4 is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylthio and C3-C6-cycloalkyl; R 5 and R 6 are each independently selected from the group consisting of hydrogen, cyano, halogen, C-C-alkyl, C-C-alkenyl, C-C-alkoxy, C-C-alkylcarbonyl, C-C-alkylthio, C-C-cycloalkyl, and C-C-cycloalkyl-C-C-alkyl; 5 and R 6 Each group is optionally R 5a or R 5 and R 6 may together with the atoms to which they are attached form a 3- to 6-membered non-aromatic carbocyclic or non-aromatic heterocyclic ring; one or more of the heteroatoms in said ring may be N, O or S(=O). 0-2one or more C atoms of the ring may be optionally substituted by C(=O), C(=S); the ring may be optionally selected from R 5a may be substituted with one or more of the same or different groups; R 5a is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thiol, amino, C1-C6-alkyl; R 7 and R 8 are each independently selected from the group consisting of hydrogen, cyano, halogen, hydroxy, C-C-alkyl, C-C-haloalkyl and C-C-alkoxy, where R 7 and R 8 Each group is optionally R 7a or R 7 and R 8 can form, together with the atoms to which they are attached, a 3- to 6-membered non-aromatic or aromatic carbocyclic or non-aromatic or aromatic heterocyclic ring; one or more of the heteroatoms in said ring may be N, O or S(=O) 0-2 one or more C atoms of the ring may be optionally substituted by C(=O) or C(=S); the ring is optionally selected from R 7a with one or more identical or different groups; provided that R 7 and R 8 When forms an aromatic ring, R 9 does not exist; R 7a is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thiol, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl and C1-C4-alkoxy-C1-C4-alkyl; R 9 are hydrogen, halogens, C6-C 10 -Aryl, C7-C 14 -Aralkyl, C6-C 10 -Aryloxy, benzyloxy, -OC(O)-C6-C10 -Aryl, O-C(O)-C-C 10 -Heterocyclyl, C2-C 10 -Heterocyclyl and C2-C 10 -heterocycloxy; heterocyclyl or heterocycloxy contains 1, 2 or 3 heteroatoms selected from N, O and S; in each case, 1 or 2 CH2 groups of the carbocycle or heterocycle may be replaced independently by a group selected from C(=O) and C(=S); C6-C 10 -Aryl, C7-C 14 -Aralkyl, C6-C 10 -Aryloxy, benzyloxy, -OC(O)-C6-C 10 -aryl, O-C(O)-C 2- C 10 -Heterocyclyl, C2-C 10 -Heterocyclyl and C2-C 10 -heterocycloxy is optionally R 9a or R 5 and R 9 may together with the atoms to which they are attached form a 3- to 12-membered non-aromatic carbocyclic or non-aromatic heterocyclic ring; one or more of the heteroatoms in said ring may be N, O or S(=O) 0-2 one or more C atoms of the ring may be optionally substituted by C(=O), C(=S); the ring may be optionally selected from R 9a may be substituted with one or more of the same or different groups; R 9a is hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloalkyl, C(R'')=N-OR', C3-C 10 -Cycloalkyloxy, C3-C 10 -Cycloalkenyl, C3-C 10 -Cycloalkenyloxy, C6-C10 -Aryl, C7-C 14 -Aralkyl, C6-C 10 -Aryloxy, C2-C 10 -Heterocyclyl and C2-C 10 -heterocyclooxy; R' is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, where each group of R' is optionally selected from halogen, cyano, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C6-C 10 -Aryl, C7-C 14 -Aralkyl and C6-C 10 -aryloxy; R'' is selected from hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl and C3-C6-cycloalkenyl; R 10 is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C3-C5-cycloalkyl and C3-C5-cycloalkyl-C1-C3-alkyl; and R 11 provides a compound selected from the group consisting of hydrogen, C1-C4-alkyl and C1-C4-alkoxy, and / or their N-oxides, metal complexes, stereoisomers, polymorphs or agriculturally acceptable salts thereof.

[0099] In one preferred embodiment, the present invention provides a compound of formula (I), wherein R 1 is selected from the group consisting of hydrogen, halogen, cyano, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl and C1-C6-alkoxy.

[0100] In another preferred embodiment, the present invention provides a compound of formula (I), wherein R 2is selected from the group consisting of hydrogen, halogen, cyano, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylthio and C3-C6-cycloalkyl.

[0101] In yet another preferred embodiment, the present invention provides compounds of formula (I), wherein R 3 is selected from the group consisting of hydrogen, halogen, oxo, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylthio and C3-C6-cycloalkyl.

[0102] In yet another preferred embodiment, the present invention provides compounds of formula (I), wherein R 4 is selected from the group consisting of hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylthio and C3-C6-cycloalkyl.

[0103] In yet another preferred embodiment, the present invention provides compounds of formula (I), wherein R 5 and R 6 are each independently selected from the group consisting of hydrogen, cyano, halogen, C-C-alkyl, C-C-alkenyl, C-C-alkoxy, C-C-alkylcarbonyl, C-C-alkylthio, C-C-cycloalkyl, and C-C-cycloalkyl-C-C-alkyl; 5 and R 6 Each group is optionally R 5a may be substituted with one or more groups; R 5a is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thiol, amino and C1-C6-alkyl.

[0104] In yet another preferred embodiment, the present invention provides compounds of formula (I), wherein R 5 and R 6may together with the atoms to which they are attached form a 3- to 6-membered non-aromatic carbocyclic or non-aromatic heterocyclic ring; one or more of the heteroatoms in said ring may be N, O or S(=O). 0-2 one or more C atoms of the ring may be optionally substituted by C(=O), C(=S); the ring may be optionally selected from R 5a may be substituted with one or more of the same or different groups; R 5a is selected from the group consisting of halogen, cyano, nitro, hydroxyl, thiol, amino and C1-C6-alkyl.

[0105] In yet another preferred embodiment, the present invention provides compounds of formula (I), wherein R 7 and R 8 are each independently selected from the group consisting of hydrogen, cyano, halogen, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl and C1-C6-alkoxy.

[0106] In yet another preferred embodiment, the present invention provides compounds of formula (I), wherein R 7 and R 8 can form, together with the atoms to which they are attached, a 3- to 6-membered non-aromatic carbocyclic or non-aromatic heterocyclic ring; one or more of the heteroatoms in said ring may be N, O or S(=O). 0-2 one or more C atoms of the ring may be optionally substituted by C(=O) or C(=S); the ring is optionally selected from R 7a with one or more identical or different groups; provided that R 7 and R 8 When forms an aromatic ring, R 9 does not exist. R 7a is halogen, cyano, nitro, hydroxyl, thiol, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C 3- C-Cycloalkyl and C 1- C 4-Alkoxy-C 1- C 4- alkyl.

[0107] In yet another preferred embodiment, the present invention provides compounds of formula (I), wherein R 9 are hydrogen, halogens, C6-C 10 -Aryl, C7-C 14 -Aralkyl, C6-C 10 -Aryloxy, benzyloxy, -OC(O)-C6-C 10 -Aryl, O-C(O)-C-C 10 -Heterocyclyl, C2-C 10 -Heterocyclyl and C2-C 10 -heterocycloxy; heterocyclyl or heterocycloxy contains 1, 2 or 3 heteroatoms selected from N, O and S; in each case, 1 or 2 CH groups of the carbocycle or heterocycle may be replaced independently by a group selected from C(=O) and C(=S); where R 9 Each group is optionally R 9a may be substituted with one or more groups.

[0108] In yet another preferred embodiment, the present invention provides compounds of formula (I), wherein R 5 and R 9 may together with the atoms to which they are attached form a 3- to 12-membered non-aromatic carbocyclic, non-aromatic heterocyclic ring; one or more of the heteroatoms in said ring may be N, O or S(=O) 0-2 one or more C atoms of the ring may be optionally substituted by C(=O), C(=S); the ring may be optionally selected from R 9a may be substituted with one or more of the same or different groups.

[0109] In yet another preferred embodiment, the present invention provides compounds of formula (I), wherein R 9ais hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloalkyl, C(R'')=N-OR', C3-C 10 -Cycloalkyloxy, C3-C 10 -Cycloalkenyl, C3-C 10 -Cycloalkenyloxy, C6-C 10 -Aryl, C7-C 14 -Aralkyl, C6-C 10 -Aryloxy, C2-C 10 -Heterocyclyl and C2-C 10 -heterocyclooxy.

[0110] In yet another preferred embodiment, the present invention provides 1-methyl-N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(3-(2-fluorophenyl)-2-methylbutan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,3-dimethyl-3-phenylbutan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-1-phenylbutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-1-phenylbutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(3-(2-chlorophenyl)-2-methylbutan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-3-phenylbutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-benzylcyclopentyl)- 1-Methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-benzylcyclohexyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(3-chlorobenzyl)cyclohexyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(2-fluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-1-(3-(trifluorophenyl) N-(1-(3,5-difluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-(tert-butyl)phenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(2-chlorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-isopropylphenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-1-(4-(trifluoromethoxy)phenyl)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(2,4-difluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(3 -fluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(3-chlorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(3,4-difluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(3,4-dichlorophenyl)-2-methylpropan-2-yl)-1-methyl-1H- Pyrrolo[2,3-b]pyridine-5-carboxamide, N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-(2-bromophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-1-(m-tolyl)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl) N-(2,4-dimethyl-1-phenylpentan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-thieno[3,2-b]pyridine-6-carboxamide, N-(2-methyl-1-phenylpropan-2-yl)-thieno[3,2-b]pyridine-6-carboxamide, 1,6-dimethyl-N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(3-(2-fluorophenyl)-2-methylbutan-2-yl)-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(2-fluorophenyl)-2,4-dimethylpentan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,3-dimethyl-3-phenylbutan-2-yl)-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(2-fluorophenyl)-2-methylbutan-2-yl) N-(1-benzylcyclopropyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(3-(2-chlorophenyl)-2-methylbutan-2-yl)-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-fluorophenyl)-2-methylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-chloro-3-fluorophenyl)-2-methylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide N-(1-(4-chlorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-chlorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(2-methyl-1-phenylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 3-bromo-1- Methyl-N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-chloro-2-fluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(3-bromophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(2-methoxyphenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-1-(p-tolyl)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-bromo-N-(2,4-dimethyl-1-phenylpentan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-N-(2,4-dimethyl-1-phenylpentan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-1-methyl-N-(2-methyl-1-phenyl 3-cyclopropyl-1-methyl-N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-cyclopropyl-1-methyl-N-(2,4-dimethyl-1-phenylpentan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-N,1-dimethyl-N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide 3-cyclopropyl-N,1-dimethyl-N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-bromo-N-(1-(2-fluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-N-(1-(2-fluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-cyclopropyl-N-(1-(2- Fluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-bromophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 3-bromo-N-(3-(2-fluorophenyl)-2-methylbutan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-N-(3-(2-fluorophenyl)-2-methylbutan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-cyclopropyl-N-(3-(2-fluorophenyl)-2-methylbutan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-chlorophenyl)-2-methylpropan-2-yl)-3-fluoro-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide , N-(2-methyl-1-phenylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 3-fluoro-N-(1-(2-fluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-chloro-3-fluorophenyl)-2-methylpropan-2-yl)-3-fluoro-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-fluoro-1-methyl-N-(2-methyl- 1-(p-tolyl)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(3-(2-chlorophenyl)-2-methylbutan-2-yl)-3-fluoro-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-fluoro-N-(1-(2-methoxyphenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-1H-pyrrolo[3,2-b]pyridine N-(1-(4-fluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(4-phenylbutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,3-dihydro-1H-inden-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-1-(naphthalen-2-yl)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-2,3-dihydro-1H-inden-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-((1-phenylcyclopropyl)methyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,3-dimethyl-4-phenylbutan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-4-methyl-3,4 -dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide, 4-methyl-N-(2-methyl-1-phenylpropan-2-yl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide, 3-chloro-N-(1-(2-chlorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-bromo-N-(1-(2-chlorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2, 3-b]pyridine-5-carboxamide, N-(1-(2-chlorophenyl)-2-methylpropan-2-yl)-3-cyclopropyl-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[3,2-b]pyridine-6-carboxamide, 3-chloro-1-methyl-N-(2-methyl-3-phenylbutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 6-methoxy-N-(2-methyl-1-phenyl N-(2,4-dimethyl-1-phenylpentan-2-yl)-6-methoxy-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-1-(4-(methylthio)phenyl)propyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 6-methoxy-1-methyl-N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-Dimethyl-1-phenylpentan-2-yl)-6-methoxy-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 6-methyl-N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-fluorophenyl)-2-methylpropan-2-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[3,2 -b]pyridine-6-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-benzylcyclopropyl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-2-oxo-2,3-dihydrooxazolo[4,5-b]pyridine-6-carboxamide, 1,2-dimethyl-N-(2-methyl-1-phenylpropan-2-yl) N-(2,3-dimethyl-3-phenylbutan-2-yl)-1,2-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-chlorophenyl)-2-methylpropan-2-yl)-1,2-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1,2-dimethyl-N-(2-methyl-1-(p-tolyl)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5 -carboxamide, N-(1-(2-fluorophenyl)-2-methylpropan-2-yl)-1,2-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(3-hydroxy-3-methyl-1-(m-tolyl)butan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(3-hydroxy-2-methyl-4-phenylbutan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(2-cyanopropan-2-yl)thieno[3,2-b, ]pyridine-6-carboxamide, N-(tert-butyl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-(trifluoromethyl)cyclopropyl)thieno[3,2-b]pyridine-6-carboxamide, N-(1,1,1-trifluoro-2-methylpropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1,1,1-trifluoro-2-methylbutan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-hydroxy-2-methylpropan-2-yl) Thieno[3,2-b]pyridine-6-carboxamide, N-(3-hydroxy-3-methyl-1-(m-tolyl)butan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(3-hydroxy-2-methyl-4-phenylbutan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-hydroxy-2-methyl-1-phenylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-hydroxy-2-methyl-1-phenylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide N-(1-(4-fluoro-3-methoxyphenyl)-1-hydroxy-2-methylpropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(2-ethyl-2-hydroxy-1-phenylbutyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5 -carboxamide, N-(1-(4-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-(4-fluoro-3-methoxyphenyl)-1-hydroxy-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 2-methyl-2-(thieno[3,2-b]pyridine-6-carboxamide)propyl 4-fluoro-3-methoxybenzoate, 2-methyl-2-(1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide)propyl 4-fluoro-2-methylbenzoate, N-(2-ethyl-2-hydroxy-1-phenylbutyl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-(2-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N- (1-(2-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-(4-fluoro-2-methylphenyl)-1-hydroxy-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2-ethyl-1-(4-fluorophenyl)-2-hydroxybutyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2-ethyl-1-(4-fluorophenyl)-2-hydroxybutyl) N-(1-(5-fluoro-2-methylphenyl)-1-hydroxy-2-methylpropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-(2-fluorophenyl)-2-methylpent-4-en-2-yl)thieno[3,2-b]pyridine-6-carboxamide, 3-bromo-N-(1-(5-fluoro-2-methylphenyl)-1-hydroxy-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide amide, N-(1-(4-fluorophenyl)-2-hydroxy-2-methylpropyl)thieno[3,2-b]pyridine-6-carboxamide, 3-chloro-N-(2,3-dihydro-1H-inden-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-N-(2-ethyl-2-hydroxy-1-phenylbutyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(2-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-N-(1-(3,5-dichlorophenyl)cyclopropyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, (S)-N-(1,1-bis(3,5-dichlorophenyl)-1-hydroxypropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-bromo-N-(1-(2-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5- Carboxamide, 3-chloro-N-(1-(3-methoxyphenyl)cyclopropyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(2-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)-1H-pyrrolo[3,2-b]pyridine-6-carboxamide, 2-(6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide)-2-methylpropyl 3-fluorobenzoate, 2-methyl-2-(1H-pyrrolo[2,3-b]pyridine-5-carboxamide do)propyl 3-fluorobenzoate, 2-(6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamido)-2-methylpropyl 2-(trifluoromethyl)benzoate, 2-(6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamido)-2-methylpropyl 2-methylbenzoate, 2-methyl-2-(5,6,7,8-tetrahydroquinoline-3-carboxamido)propyl 2-(trifluoromethyl)benzoate, 2-methyl-2-(5,6,7,8-tetrahydroquinoline-3 -carboxamido)propyl 2-methylbenzoate, 2-methyl-2-(5,6,7,8-tetrahydroquinoline-3-carboxamido)propyl 3-fluorobenzoate, 2-(3-chloro-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamido)-2-methylpropyl 3-fluorobenzoate, N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamido, 2-methyl-2-(1H-pyrrolo[3,2-b]pyridine-6-carboxamido)propyl 3-fluorobenzoate, 2-methyl-2-(1H-pyrrolo[2,3-b]pyridine-5-carboxamido)propyl 2-(trifluoromethyl)benzoate, N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-methyl -2-(thieno[3,2-b]pyridine-6-carboxamido)propyl 2-(trifluoromethyl)benzoate, 2-methyl-2-(1H-pyrrolo[3,2-b]pyridine-6-carboxamido)propyl 2-(trifluoromethyl)benzoate, 2-methyl-2-(thieno[3,2-b]pyridine-6-carboxamido)propyl 2-methylbenzoate, N-(1-(4-fluoro-3-methoxyphenyl)-1-hydroxy-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamido 2-methyl-2-(1H-pyrrolo[2,3-b]pyridine-5-carboxamide)propyl 2-methylbenzoate, 2-methyl-2-(1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide)propyl 2-(trifluoromethyl)benzoate, 2-methyl-2-(1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide)propyl 3-fluorobenzoate, N-(1-(4-fluorophenyl)-2-hydroxy-2-methylpropyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-fluoro-2-methylphenyl)-1-hydroxy-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-(4-fluoro-2-methylphenyl)-1-hydroxy-2-methylpropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-(2-fluorophenoxy)-2,4-Dimethylpent-4-en-2-yl)-1H-pyrrolo[3,2-b]pyridine-6-carboxamide, 3-bromo-N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 2-(3-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine-5- carboxamido)-2-methylpropyl 3-fluorobenzoate, 3-chloro-N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 2-(3-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide)-2-methylpropyl 2-(trifluoromethyl)benzoate, N-(1-(4-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)-1-methyl-1H-pyrrolo[2, 3-b]pyridine-5-carboxamide, N-(1-(4-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)thieno[3,2-b]pyridine-6-carboxamide, 2-(3-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide)-2-methylpropyl 2-methylbenzoate, N-(1-(5-fluoro-2-methylphenyl)-1-hydroxy-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-((2- fluorobenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-((2-cyanobenzyl)oxy)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-((2-fluorobenzyl)oxy)-2-methylpropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-((2-fluorobenzyl)oxy)-2-methylpropan-2-yl)-6,7-Dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-((2-chlorobenzyl)oxy)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-((2-chlorobenzyl)oxy)-2-methylpropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-((2-cyanobenzyl)oxy)-2-methylpropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, 3-bromo-N-(1 -((2-fluorobenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-bromo-N-(1-((2-chlorobenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-bromo-N-(1-((2-cyanobenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-((2-chloro-5-fluoro N-(1-((2-chloro-5-fluorobenzyl)oxy)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-((2-chloro-5-fluorobenzyl)oxy)-2-methylpropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-((2,4-dimethylbenzyl)oxy)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-((2,4-dimethylbenzyl)oxy)-2-methylpropan-2-yl)- 3-Bromo-N-(1-((2,4-dimethylbenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2-methyl-1-(pyridin-2-yloxy)propan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 3-Bromo-1-methyl-N-(2-methyl-1-(pyridin-2-yloxy)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-((2-chloropyridin-4-yl)oxy)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-((2-chloropyridin-4-yl)oxy)-2-methylpropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, 3-bromo-N-(1-((2-chloropyridin-4-yl)oxy)-2-methylpropan-2-yl) -methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-((5-fluoropyridin-2-yl)oxy)-2-methylpropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, 3-chloro-N-(1-((2-chlorobenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro -N-(1-((2-cyanobenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 2-chloro-N-(2-methyl-1-phenylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-chloro-N-(2,4-dimethyl-1-phenylpentan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine dine-3-carboxamide, N-(2-methyl-1-(pyridin-2-yloxy)propan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, 3-chloro-N-(1-((2-fluorobenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-N-(1-((2-chloro-5-fluorobenzyl)oxy)-2-methylpropane-2-, 3-bromo-N-(1-((5-fluoropyridin-2-yl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 2-methoxy-N-(2-methyl-1-phenylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 3-chloro-N-(1-((2,4-dimethylbenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide Methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-1-methyl-N-(2-methyl-1-(pyridin-2-yloxy)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-N-(1-((2-chloropyridin-4-yl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-N-(1-((5-fluoropyridin-2-yl)oxy)-2-methylpropan-2-yl)- 1-Methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-N-(1-((5-cyanopyridin-2-yl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-((5-cyanopyridin-2-yl)oxy)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-((5-cyanopyridin-2-yl)oxy)-2-methylpropan-2-yl)thienoic acid No[3,2-b]pyridine-6-carboxamide, 3-bromo-N-(1-((5-cyanopyridin-2-yl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-((2-chloro-5-fluorobenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-((2,5-dimethylbenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-1-(pyridin-2-yloxy)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-((2-chloropyridin-4-yl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-((5-fluoropyridin-2-yl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide amide, N-(1-((5-cyanopyridin-2-yl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-bromo-N-(1-((2-chloro-5-fluorobenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-((5-fluoropyridin-2-yl)oxy)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide amide, N-(1-((2-cyanobenzyl)oxy)-2-methylpropan-2-yl)-2-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-chloro-N-(1-((2-cyanobenzyl)oxy)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-((2,4-dimethylbenzyl)oxy)-2-methylpropan-2-yl)-2-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide Boxamide, 2-chloro-N-(1-((2,4-dimethylbenzyl)oxy)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-2-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-(2-fluorophenyl)propan-2-yl)-N-methoxy-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 2-(2-methoxy-6,7-Dihydro-5H-cyclopenta[b]pyridine-3-carboxamide)-2-methylpropyl 3-fluorobenzoate, 2-Methoxy-N-(2-methyl-1-(pyridin-2-yloxy)propan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-Chloro-N-(2-methyl-1-(pyridin-2-yloxy)propan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-((2-chloropyridin-4-yl)oxy)-2-methylpropyl 2-chloro-N-(1-((2-chloropyridin-4-yl)oxy)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-benzylcyclopropyl)-2-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-benzylcyclopropyl)-2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine-3 -carboxamide, 2-methoxy-N-((1-phenylcyclopropyl)methyl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-chloro-N-((1-phenylcyclopropyl)methyl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-methoxy-N-(4-phenylbutan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-chloro-N-(4-phenylbutan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide Lysine-3-carboxamide, 2-chloro-N-(1-phenylcyclopropyl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-methoxy-N-(1-phenylcyclopropyl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-(2-fluorophenyl)propan-2-yl)-N-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-chloro-N-(1-(2-fluorophenyl)propan-2-yl)-N-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide7-Dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-(2-fluorophenyl)propan-2-yl)-N-methoxy-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 2-chloro-N-(1-(4-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-chloro-N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-6,7-dihydro-5H-cyclopenta[b ]pyridine-3-carboxamide, 2-(2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide)-2-methylpropyl 3-fluorobenzoate, 2-methoxy-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-chloro-N-(2-methyl-1-phenylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-chloro-N-(2,4-dimethyl-1-phenyl 2-chloro-N-(1-((2,4-dimethylbenzyl)oxy)-2-methylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-1,2-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-( 1-benzylcyclopropyl)-1,2-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 2-chloro-N-(1-((2-chlorobenzyl)oxy)-2-methylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-chloro-N-(1-((2-fluorobenzyl)oxy)-2-methylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-chloro-N-(1-((2-cyanobenzyl)oxy)-2-methylpropan-2-yl)-5,6,7,8-Tetrahydroquinoline-3-carboxamide, 2-chloro-N-(1-(4-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-chloro-N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(1-((2-chlorobenzyl)oxy)-2-methylpropan-2-yl)-2-methoxy-6,7-dihydro-5H-cyclopenta[b]pi Lysine-3-carboxamide, N-(1-((2-fluorobenzyl)oxy)-2-methylpropan-2-yl)-2-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-(4-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)-2-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-2-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide Ropenta[b]pyridine-3-carboxamide, N-(1-((2-chloro-5-fluorobenzyl)oxy)-2-methylpropan-2-yl)-2-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-(4-fluorophenyl)-2-methylpropan-2-yl)-1,2-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1,2-dimethyl-N-(2-phenylpropyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1,2-dimethyl-N -((1-phenylcyclopropyl)methyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 2-chloro-N-methoxy-N-(1-phenylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 4-methyl-N-(1-phenylcyclopropyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide, N-(1-(4-fluorophenyl)cyclopropyl)-4-methyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide, 4-methyl-N-((1-phenylcyclopropyl)methyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide, N-(1-benzylcyclopropyl)-4-methyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide, 2-chloro-N-(2-methyl-1-(pyridin-2-yloxy)propan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-chloro-N-(1-((2-chloropyridine 2-Chloro-N-(1-((2-chloro-5-fluorobenzyl)oxy)-2-methylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-chloro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-chloro-N-(1-((2-chloro-5-fluorobenzyl)oxy)-2-methylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-methoxy-N-(2-methyl-1-(pyridin-2-yloxy)propan 2-Methoxy-N-(2-methyl-1-phenylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-2-methoxy-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-Methoxy-N-(1-phenylcyclopropyl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-Methoxy-N-((1-phenylcyclopropyl)methyl)-5 ,6,7,8-tetrahydroquinoline-3-carboxamide, 2-methoxy-N-(4-phenylbutan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(1-(4-fluorophenyl)-2-methylpropan-2-yl)-2-methoxy-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-chloro-N-(4-phenylbutan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-chloro-N-(1-(4-fluorophenyl)-2-methylpropan-2-yl)-5,6,7,8-Tetrahydroquinoline-3-carboxamide, N-(1-(4-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(1-(4-fluorophenyl)cyclopropane 4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-chloro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-Methoxy-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 1-methyl-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-1-methyl-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan 3-chloro-6-methoxy-1-methyl-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 6,6-difluoro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)-5,6,7,8-tetrahydroquinoline, -3-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-6,6-difluoro-5,6,7,8-tetrahydroquinoline-3-carboxamide, 4-chloro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 4-chloro-N-(2,4-dimethyl-1-phenylpentan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 4-chloro 4-chloro-N-(2,4-dimethyl-1-phenylpentan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-4-methoxy-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-4-methoxy-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-4-methoxy-5,6,7,8-tetrahydroquinoline-3-carboxamide N-(2,4-dimethyl-1-phenylpent-4-en-2-yl)-4-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 4-chloro-N-(1-(2-fluorophenyl)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 4-chloro-N-(1-(4-fluorophenyl)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, The present invention provides a compound of formula (I) selected from N-(1-(2-fluorophenyl)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-(2-fluorophenyl)-2-methylpropan-2-yl)-4-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, or N-(1-(4-fluorophenyl)-2-methylpropan-2-yl)-4-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide.

[0111] Agriculturally acceptable salts of the compounds of formula (I) include in particular their cation salts or their acid addition salts, whose cations and anions, respectively, do not adversely affect the fungicidal action of the compounds of formula (I).Suitable cations are therefore in particular the ions of alkali metals, preferably sodium and potassium, alkaline earth metals, preferably calcium, magnesium and barium, transition metals, preferably manganese, copper, zinc and iron, and also ammonium ions, which may optionally carry 1 to 4 C1-C4-alkyl substituents and / or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, and also phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium.

[0112] The salts thus obtained likewise have bactericidal properties.

[0113] Useful anions of acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate, which can be formed by reacting the compounds of formula (I) with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

[0114] The compounds of the present invention can exist in pure form or as a mixture of different possible isomers, such as racemates, individual stereoisomers, or structural isomers, or optically active forms. The various stereoisomers include enantiomers, diastereomers, chiral isomers, atropisomers, conformers, rotamers, tautomers, optical isomers, polymorphs, and geometric isomers. Any desired mixture of these isomers is included within the scope of the claims of the present disclosure. Those skilled in the art will understand that one stereoisomer may be more active and / or exhibit beneficial effects when enriched with respect to other isomers or separated from other isomers. Furthermore, those skilled in the art will know the processes or methods or techniques to separate, enrich, and / or selectively prepare said isomers.

[0115] The compounds of formula (I) can exist in different crystal modifications, which may have different biological activities.They also form part of the subject matter of the present invention.The compounds of formula (I) can exist in atropisomers resulting from restricted rotation around a single bond of asymmetric groups.They also form part of the subject matter of the present invention.

[0116] Compounds selected from formula (I) (including all stereoisomers, N-oxides and salts thereof) can generally exist in multiple forms. Thus, compounds of formula (I) include all crystalline and non-crystalline forms of the compounds represented by formula (I). Non-crystalline forms include embodiments that are solids, such as waxes and gums, and embodiments that are liquids, such as solutions and melts. Crystalline forms include embodiments that represent essentially a single crystal type and embodiments that represent a mixture of polymorphs (i.e., different crystal types).

[0117] The following scheme shows an approach for preparing compounds of formula (I). The following description and examples are provided for illustrative purposes only and should not be construed as limiting with respect to substituents or substitution patterns. Furthermore, the reagents, solvents and reaction conditions mentioned are for illustrative purposes only and should not be construed as limiting.

[0118] In one embodiment, the present invention provides a method for the synthesis of a compound of formula (I).

[0119] The compound of formula (I) can be prepared by any of the following methods. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 11 The definitions of X, Z1 and Z2 are as stated above in the detailed description of the invention unless otherwise specified.

[0120] Scheme 1 [ka] X is O and R 11 Compounds of formula (I), in which is H, can be prepared by coupling reaction of compounds of formula (1) and formula (2) in the presence of suitable coupling reagents known in the literature (Comprehensive Organic Synthesis (2nd ed.) (2014), 6, 427-478; Synthesis, 2019, 51, 2261-2277). Suitable coupling reagents are selected from 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, N,N'-dicyclohexylcarbodiimide, benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate, 3-[bis(dimethylamino)methylimyl]-3H-benzotriazole-1-oxide hexafluorophosphate, and other coupling reagents known in amide synthesis. (Chem. Soc. Rev., 2009, 38, 606-631)

[0121] Scheme 2 [ka] X is O and R 11 Compounds of formula (I), wherein is H, can be prepared by a Brønsted acid catalyzed Ritter reaction of compounds of formula (3) with a suitable secondary or tertiary alcohol of formula (4a) in the presence of a suitable Brønsted acid, such as sulfuric acid, following procedures similar to those described in WO2019154665 (Scheme 2).

[0122] Scheme 3 [ka] X is O and R 11 Compounds of formula (IA), in which is H, can be obtained by coupling of a suitable acid of formula (1a) with a suitable amine of formula (2) in the presence of a suitable coupling reagent known in the literature (Comprehensive Organic Synthesis (2nd ed.) (2014), 6, 427-478; Synthesis 2019, 51, 2261-2277). Suitable coupling reagents are selected from 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, N,N'-dicyclohexylcarbodiimide, benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate, 3-[bis(dimethylamino)methylimyl]-3H-benzotriazole-1-oxide hexafluorophosphate, and other coupling reagents known for amide synthesis. (Chem. Soc. Rev., 2009, 38, 606-631)

[0123] Scheme 4 [ka] X is O and R 11Compounds of formula (IA), wherein is H, can be obtained by Brønsted acid catalyzed Ritter reaction of compounds of formula (5) with a suitable secondary or tertiary alcohol of formula (4a) in the presence of a suitable acid, such as sulfuric acid, following procedures similar to those described in WO2019154665 (Scheme 4).

[0124] Scheme 5 [ka] X is O and R 11 Compounds of formula (IA) in which is H can be obtained by reacting a secondary or tertiary alcohol of formula (5) with a compound of formula (4b) in a Ritter reaction, as shown in Scheme 5 (Synthesis, 2021, 53, 146-160).

[0125] Scheme 6 [ka] Compounds of formula (7) can be obtained by halogenating the pyrrolopyridine nitrile of formula (6) with a suitable reagent such as Select Fluor, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, and other halogenating reagents known in the literature (WO2020012424). Compounds of formula (7) can be obtained by Suzuki coupling reaction with a suitable alkylboronate to give Z1 as CR. 4 This conversion can also be carried out using a variety of coupling reagents known in WO2014004064 (Scheme 6).

[0126] Scheme 7 [ka] Substituted pyrrolopyridine nitriles of formula (1a) where Z1 is S can be obtained by hydrolysis of compounds of formula (5) in the presence of a suitable reagent such as a basic reagent selected from sodium hydroxide, potassium hydroxide, etc., or a suitable acid selected from concentrated hydrochloric acid, sulfuric acid, etc. Hydrolysis of the nitriles of formula (5) can also be achieved by methods known in the literature (WO2009155017), as shown in Scheme 7.

[0127] Scheme 8 [ka] X is O and R 11 Compounds of formula (IB) in which is H can be obtained by coupling a suitable acid of formula (1b) with a suitable amine of formula (2) in the presence of a suitable coupling reagent known in the literature (Comprehensive Organic Synthesis (2nd ed.) (2014), 6, 427-478; Synthesis; 2019, 51, 2261-2277). Suitable coupling reagents are selected from 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, N,N'-dicyclohexylcarbodiimide, benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate, 3-[bis(dimethylamino)methylimyl]-3H-benzotriazole-1-oxide hexafluorophosphate, and other coupling reagents known for amide synthesis. (Chem. Soc. Rev., 2009, 38, 606-631)

[0128] Scheme 9 [ka] X is O and R 11Compounds of formula (IC) where is H can be obtained by coupling a suitable acid of formula (1c) with a suitable amine of formula (2) in the presence of a suitable coupling reagent known in the literature (Comprehensive Organic Synthesis (2nd ed.) (2014), 6, 427-478; Synthesis, 2019, 51, 2261-2277). Suitable coupling reagents are selected from 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, N,N'-dicyclohexylcarbodiimide, benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate, and 3-[bis(dimethylamino)methylimyl]3H-benzotriazole-1-oxide hexafluorophosphate, as well as other coupling reagents known for amide synthesis. (Chem. Soc. Rev., 2009, 38, 606-631)

[0129] Scheme 10 [ka] Heteroaryl acids of formula (1c) where Z1 is O can be obtained by reaction of heteroaryl esters of formula (9) with suitable reagents used to synthesize carbamates from amino alcohols, such as 1,1'-carbonyldiimidazole, chloroformates, triphosgene, etc., as shown in Scheme 10 (CN111943885). Hydrolysis of compounds of formula (10) to obtain acids of formula (1c) can be accomplished with suitable reagents such as lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, and others known in the literature.

[0130] Scheme 11 [ka] X is O and R 11Compounds of formula (ID) where is H can be obtained by coupling a suitable acid of formula (1d) with a suitable amine of formula (2) in the presence of a suitable coupling reagent known in the literature (Comprehensive Organic Synthesis (2nd Edition) (2014), 6, 427-478; Synthesis, 2019, 51, 2261-2277). Suitable coupling reagents are selected from 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, N,N'-dicyclohexylcarbodiimide, benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate and 3-[bis(dimethylamino)methylimyl]-3H-benzotriazole-1-oxide hexafluorophosphate, as well as other coupling reagents known for amide synthesis. (Chem. Soc. Rev., 2009, 38, 606-631)

[0131] Scheme 12 [ka] X is O and R 11Compounds of formula (IE) where is H can be prepared by coupling with suitable coupling reagents known in the literature (Comprehensive Organic Synthesis (2nd ed.) (2014), 6, 427-478; Synthesis, 2019, 51, 2261-2277), such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, N,N'-dicyclohexylcarbodiimide, benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate and 3-[bis(dimethylamino) The amides can be obtained by coupling the appropriate acid of formula (1e) with the appropriate amine of formula (2) in the presence of methylimyl]3H-benzotriazole-1-oxide hexafluorophosphate, as well as other coupling reagents known for the synthesis of amides. (Chem. Soc. Rev., 2009, 38, 606-631)

[0132] Scheme 13 [ka] X is O and R 11Compounds of formula (I)-F, in which is H, can be obtained by coupling of a suitable acid of formula (1f) with a suitable amine of formula (2) in the presence of suitable coupling reagents known in the literature (Comprehensive Organic Synthesis (2nd Edition) (2014), 6, 427-478; Synthesis, 2019, 51, 2261-2277), such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, N,N'-dicyclohexylcarbodiimide, benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate and 3-[bis(dimethylamino)methylimyl]3H-benzotriazole-1-oxide hexafluorophosphate, as well as other coupling reagents known in amide synthesis. (Chem. Soc. Rev., 2009, 38, 606-631)

[0133] In one embodiment, the present invention provides an agricultural chemical composition comprising a compound of formula (I), an agriculturally acceptable salt, metal complex, structural isomer, stereoisomer, diastereoisomer, enantiomer, chiral isomer, atropisomer, conformer, rotamer, tautomer, optical isomer, polymorph, geometric isomer, or N-oxide thereof, optionally together with one or more additional active ingredients, optionally together with adjuvants such as inert carriers or other essential ingredients such as surfactants, additives, solid diluents and liquid diluents.

[0134] The agrochemical composition comprises a fungicidally effective amount of the compound of formula (I).The term "effective amount" refers to the amount of the composition or the compound of formula (I) that is sufficient to control harmful fungi on cultivated plants or to protect materials, and does not cause substantial damage to the treated plants.Such amount can vary widely and depends on various factors such as the fungal species to be controlled, the cultivated plants or materials to be treated, climatic conditions and the specific compound of formula (I) used.

[0135] The term "anticidally effective amount" refers to an amount of such a compound or combination of such compounds that can produce an effect on fungal growth. A controlling or modifying effect includes any kind of deviation from natural occurrence, such as killing, retardation, etc., and prevention includes the formation of a barrier or other defense in or on the plant to prevent fungal infection.

[0136] The compounds of the present disclosure can be applied by any of a variety of known techniques, either as the compounds themselves or as formulations containing these compounds.For example, the compounds can be applied to the roots or leaves of plants for the control of various fungi without damaging the commercial value of the plants.The materials can be applied in the form of any of the commonly used formulation types, such as solutions, dusts, wettable powders, flowable concentrates, or emulsifiable concentrates.

[0137] Preferably, the compound of the present disclosure is applied in the form of a formulation that includes one or more of the compounds of formula (I) together with a phytologically acceptable carrier.Concentrated formulations can be dispersed in water or other liquids for application, or the formulations can be dust or granular, and then applied without further treatment.Formulations can be prepared according to the procedures that are conventional in the agricultural chemical field.

[0138] The present disclosure contemplates all media in which one or more compounds can be formulated to be delivered and used as fungicides. Typically, the formulations are applied as aqueous suspensions or emulsions. Such suspensions or emulsions can be made from water-soluble, water-suspendable, or emulsifiable formulations, which are solids, usually known as wettable powders, or liquids, usually known as emulsifiable concentrates, aqueous suspensions, or suspension concentrates. As will be readily understood, any material to which these compounds can be added as antifungal agents can be used, provided that it provides the desired utility without significantly inhibiting the activity of these compounds.

[0139] The term "plant health" is understood to describe the state of a plant and / or its products, determined solely or in combination with several indicators, such as yield (e.g. increased biomass and / or increased content of useful components), plant vigor (improved plant growth and / or greening of leaves ("greening effect"), quality (e.g. improved content or composition of certain components), resistance to abiotic and / or biotic stresses, etc. The above mentioned indicators of plant health may be interdependent or may be the result of each other.

[0140] The compounds of formula (I) are used as such or in the form of a composition to treat with an effective amount of active substance to protect fungi or plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms, from fungal attack. This application can be carried out both before and after the infection of plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms, by fungi.

[0141] Plant propagation material may be protectably treated with the compounds of formula (I), combinations and compositions thereof at the time of planting or before transplanting.

[0142] In another embodiment, the present invention provides a composition comprising at least one compound of formula (I) and seeds, wherein the amount of the compound of formula (I) in the composition ranges from 0.1 g ai (active ingredient per gram) to 1 kg ai (active ingredient per kilogram) per 100 kg of seeds.

[0143] The compounds of formula (I), their oxides, metal complexes, isomers, polymorphs or agriculturally acceptable salts thereof can be converted into conventional types of agrochemical compositions, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, presses, capsules and mixtures thereof. Examples of such composition types are suspensions (e.g. SC, OD, FS), emulsifier concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, lozenges, wettable 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), insecticidal articles (e.g. LN), as well as gel formulations (e.g. GF) for the treatment of plant propagation materials such as seeds. These and further composition types are defined in the "Catalogue of pesticide formulation types and international coding system" (Technical Monograph No. 2, 6th Edition, May 2008, CropLife International).

[0144] The compositions mentioned are prepared in known manner, such as those 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).

[0145] Examples of suitable auxiliaries for the formulations and / or agrochemical compositions according to the invention are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, moisturizers, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, antifoaming agents, colorants, tackifiers and binders.

[0146] Suitable solvents and liquid carriers in this case are, for example, water and organic solvents, such as medium to high boiling mineral oil fractions, e.g. kerosene, diesel oil, oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e.g. toluene, paraffins, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; dimethyl sulfoxide; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, γ-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof. Suitable solid carriers or fillers include, for example, mineral earths, such as silicates, 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; products of plant origin, such as cereal meals, bark meals, wood meals, nut meals, and mixtures thereof.

[0147] Suitable surfactants are surface active 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 listed in McCutcheon's, Vol.1: "Emulsifiers & Detergents", McCutcheon's Directories, Glen Rock, USA, 2008 (International Edition, North American Edition).

[0148] Suitable anionic surfactants are, for example, the alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates and their mixtures.Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, α-olefinsulfonates, ligninsulfonates, 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 are sulfates of fatty acids and oils, sulfates of ethoxylated alkylphenols, sulfates of alcohols, sulfates of ethoxylated alcohols or sulfates of fatty acid esters.Examples of phosphates are phosphoric acid esters.Examples of carboxylates are alkylcarboxylates, carboxylated alcohols or alkylphenol ethoxylates.

[0149] Suitable nonionic surfactants are, for example, alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters alkoxylated with 1 to 50 equivalents. Ethylene oxide and / or propylene oxide, preferably ethylene oxide, can be used for the alkoxylation.

[0150] 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 surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vinyl alcohol or vinyl acetate.

[0151] Suitable cationic surfactants are, for example, quaternary surfactants, such as quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are, for example, block polymers of the AB or ABA type, including blocks of polyethylene oxide and polypropylene oxide, or block polymers of the ABC type, including alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are, for example, polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.

[0152] Suitable adjuvants are compounds that have little or no insecticidal activity themselves and improve the biological performance of the compound of formula (I) on the target. Examples are surfactants, mineral or vegetable oils, and other adjuvants. Further examples are listed in Knowles, "Adjuvants and Additives", Agrow Reports DS256, T&F Informa UK, 2006, Chapter 5.

[0153] Suitable thickening agents are, for example, polysaccharides (eg, xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or not), polycarboxylates, and silicates.

[0154] Suitable fungicides are, for example, bronopol and isothiazolinone derivatives, such as alkylisothiazolinones and benzoisothiazolinones.

[0155] Suitable antifreeze agents are, for example, ethylene glycol, propylene glycol, urea and glycerin.

[0156] Suitable antifoaming agents are, for example, silicones, long chain alcohols, and fatty acid salts.

[0157] Suitable colorants (e.g. red, blue, green) are, for example, pigments with low water solubility and water soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin, azo and phthalocyanine colorants).

[0158] Suitable tackifiers or binders include, for example, polyvinylpyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.

[0159] Examples of composition types and their preparation are as follows:

[0160] i) Water-soluble concentrates (SL, LS) 10-60% by weight of a compound of formula (I) and 5-15% by weight of a wetting agent (e.g., an alcohol alkoxylate) are dissolved in water and / or a water-soluble solvent (e.g., alcohols) to a concentration of 100% by weight. The active substance dissolves upon dilution with water.

[0161] ii) Dispersible Concentrate (DC) 5-25% by weight of a compound of formula (I) and 1-10% by weight of a dispersing agent (e.g., polyvinylpyrrolidone) are dissolved in an organic solvent (e.g., cyclohexanone) to a concentration of 100% by weight. Upon dilution with water, the active substance disperses.

[0162] iii) Emulsion (EC) 15-70% by weight of a compound of formula (I) and 5-10% by weight of an emulsifier (e.g., calcium decylbenzenesulfonate and castor oil ethoxylate) are dissolved in a water-insoluble organic solvent (e.g., aromatic hydrocarbon) to make 100% by weight. Dilute with water to obtain an emulsion of the active substance.

[0163] iv) Emulsions (EW, EO, ES) 5-40% by weight of a compound of formula (I) and 1-10% by weight of an emulsifier (e.g., calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon). This mixture is made up to 100% by weight in water with the emulsifier to form a homogeneous emulsion. Upon dilution with water, an emulsion of the active substance is obtained.

[0164] v) Suspensions (SC, OD, FS) In an agitator ball mill, 20-60% by weight of a compound of formula (I) is ground and mixed with 2-10% by weight of a dispersant and wetting agent (e.g. sodium lignosulfonate and alcohol ethoxylates), 0.1-2% by weight of a thickener (e.g. xanthan gum) and water to 100% by weight to obtain a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance. In compositions of the FS type, up to 40% by weight of a binder (e.g. polyvinyl alcohol) is added.

[0165] vi) Water-dispersible granules and water-soluble granules (WG, SG) 50-80% by weight of the compound of formula (I) is milled to 100% by weight with the addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylates) and prepared as water-dispersible or water-soluble granules by technical equipment (e.g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.

[0166] vii) Water-dispersible and water-soluble powders (WP, SP, WS) 50-80% by weight of a compound of formula (I) is mixed with 1-5% by weight of a dispersing agent (e.g., sodium lignosulfonate), 1-3% by weight of a wetting agent (e.g., alcohol ethoxylate) and a solid carrier to make 100% by weight and ground in a rotor-stator mill. Dilution with water gives a stable dispersion or solution of the active substance.

[0167] viii) Gel (GW, GF) 5-25% by weight of a compound of formula (I), 3-10% by weight of a dispersant (e.g., sodium lignosulfonate), 1-5% by weight of a thickener (e.g., carboxymethylcellulose) and water are added to make 100% by weight and ground in a stirred ball mill to obtain a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.

[0168] ix) Microemulsion (ME) 5-20 wt% of a compound of formula (I), 5-30 wt% of an organic solvent blend (e.g., fatty acid dimethylamide and cyclohexanone), 10-25 wt% of a surfactant blend (e.g., alcohol ethoxylate and arylphenol ethoxylate), and water added to 100 wt%. The mixture is stirred for 1 hour to spontaneously generate a thermodynamically stable microemulsion of the actives.

[0169] x) Microcapsules (CS) An oil phase containing 5-50% by weight of a compound of formula (I), 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, diacrylate or triacrylate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Poly(meth)acrylate microcapsules are formed by radical polymerization. Alternatively, an oil phase containing 5-50% by weight of a compound of formula (I) of 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). Upon addition of a polyamine (e.g., hexamethylenediamine), polyurea microcapsules containing the active substance are formed. The monomer is 1-10% by weight. The weight percentages relate to the total CS composition.

[0170] xi) Dispersible Powders (DP, DS) 1-10% by weight of a compound of formula (I) is finely ground and mixed thoroughly with a solid carrier (eg, finely ground kaolin) to make up to 100% by weight.

[0171] xii) Granules (GR, FG) 0.5-30% by weight of a compound of formula (I) is finely ground to 100% by weight with a solid carrier (eg, a silicate). Granulation is carried out by extrusion, spray drying or in the fluidized bed.

[0172] xiii) Ultra-low volume liquid 1 to 50% by weight of the compound of formula (I) is dissolved in an organic solvent (eg, aromatic hydrocarbon) to make up 100% by weight.

[0173] The compositions of types i) to xiii) may, if necessary, contain further auxiliaries such as 0.1 to 1% by weight of a bactericide, 5 to 15% by weight of an antifreeze agent, 0.1 to 1% by weight of an antifoaming agent and 0.1 to 1% by weight of a coloring agent.

[0174] The agrochemical composition generally comprises 0.01 to 95% by weight, preferably 0.1 to 90%, in particular 0.5 to 75% of the active ingredient (ai). The active ingredient (ai) is used with a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectroscopy).

[0175] For the purpose of treating plant propagation material, in particular seeds, seed treatment solutions (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually used. The compositions in question, after dilution 2-10 times, give active substance concentrations in the ready-to-use preparations of 0.01-60% by weight, preferably 0.1-40% by weight.

[0176] When used in plant protection, the amount of active substance applied is, depending on the type of effect desired, between 0.001 and 2 kg / ha, preferably between 0.005 and 2 kg / ha, more preferably between 0.05 and 1.0 kg / ha and in particular between 0.1 and 0.5 kg / ha.

[0177] In the treatment of plant propagation material such as seeds, e.g. by spraying, coating or soaking the seeds, the amount of active substance generally required is in the range from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g, most preferably from 5 to 100 g per 100 kg of plant propagation material (preferably seeds).

[0178] When used in the protection of materials or stored products, the amount of active substance applied depends on the type of application area and the desired effect. The amounts usually applied in the protection of materials range from 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.

[0179] Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients, and further pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safety agents, biopesticides) can be added to the active substances or compositions containing them as premixes or, where appropriate, as tank mixes until just before use. These agents can be mixed with the compositions of the invention in a weight ratio of 1:100 to 100:1, preferably 1:20 to 20:1.

[0180] Pesticides are generally chemical or biological agents (insecticidal active ingredients, compounds, compositions, viruses, bacteria, antimicrobials, disinfectants, etc.) that deter, incapacitate, kill, or otherwise deter pests through their effects. Target pests include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microorganisms that destroy property, cause nuisances, spread disease, or act as vectors for disease.

[0181] The term "pesticides" also includes plant growth regulators, which alter the expected growth, flowering, or reproduction rate of a plant; defoliants, which cause leaves or other foliage to fall from a plant, usually to facilitate harvest; desiccants, which promote the drying of living tissues, such as unwanted plant surfaces; plant activators, which activate plant physiology for defense against certain pests; safety agents, which reduce the unwanted herbicidal action of pesticides on crop plants; and plant growth promoters, which affect plant physiology (e.g., to increase plant growth, biomass, yield, or other quality parameters of the harvestable commodity of a crop).

[0182] The user usually applies the composition of the present invention from a pre-dosing device, a knapsack sprayer, a spray tank, a sprayer or an irrigation system. Usually, the agrochemical composition is prepared to a desired application concentration with water, a buffer, and / or further auxiliaries, thus obtaining the ready-to-use spray solution or agrochemical composition of the present invention. Usually, the ready-to-use spray solution is applied at 20 to 2000 liters, preferably 30 to 400 liters per hectare of agriculturally useful area.

[0183] In one embodiment, the present invention provides a combination comprising a compound of formula (I) and at least one further pesticidal active substance selected from the group consisting of fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safety agents, plant growth regulators, antibiotics, fertilizers and nutrients.

[0184] The compounds of formula (I), combinations and compositions containing them, when used as fungicides together with other fungicides, can result in an increased spectrum of fungicidal activity or the prevention of the development of fungicide resistance, and in many cases, extraordinary and unexpected effects.

[0185] The present invention also relates to a combination comprising at least one compound of formula (I) and at least one further insecticidal active substance selected from the group consisting of fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safety agents, plant growth regulators, antibiotics, fertilizers and nutrients. The insecticidal active substances reported on pages 36-43 of WO2015185485 and on pages 42-56 of WO2017093019 can be used in combination with the compound of formula (I).

[0186] The active substances referred to as ingredient 2, their preparation and their activity, e.g., against harmful fungi, are known (see: http: / / www.alanwood.net / pesticides / ); these substances are commercially available. The compounds described in the IUPAC nomenclature, their preparation and their insecticidal activity are also known. (Reference: Can. J. Plant Sci. 48(6), 587-94, 1968; EP141317; EP152031; EP226917; EP243970; EP256503; EP428941; EP532022; EP1028125; EP1035122; EP1201648; EP1122244, JP2002316902; DE19650197; DE10021412; DE102005009458; US3296272; US3325503; WO9846608; WO9914187; WO9924413; WO9927783; WO0029404; WO0046148; WO0065913; WO0154501; WO0156358; WO0222583; WO0240431; WO0310149; WO0311853; WO0314103; WO0316286; WO0353145; WO0361388; WO0366609; WO0374491; WO0449804; WO0483193; WO05120234; WO05123689; WO05123690; WO0563721; WO0587772; WO0587773; WO0615866; WO0687325; WO0687343; WO0782098; WO0790624; WO11028657; WO2012168188; WO2007006670; WO201177514; WO13047749; WO10069882; WO13047441; WO0316303; WO0990181; WO13007767; WO1310862; WO13127704; WO13024009; WO13024010; WO13047441; WO13162072; WO13092224 and WO11135833)

[0187] The present invention further relates to agrochemical mixtures comprising at least one compound of formula (I) (component 1) and at least one further active substance useful in plant protection.

[0188] Additional efficacy can be obtained by applying the compounds of formula (I) together with at least one insecticidally active compound.

[0189] This can be obtained by applying the compound of formula (I) and at least one further insecticidal active substance simultaneously, simultaneously (for example, as a tank mix), or separately or successively, the time interval between each application being selected to ensure that the first applied active substance is present at the site of action in sufficient amount when the further insecticidal active substance is applied. The order of application is not essential to the implementation of the present invention.

[0190] In the case of successive application of the compound of formula (I) and the insecticidal active substance, the time between both applications may vary, for example, between 2 hours and 7 days. A broader range is also possible, between 0.25 hours and 30 days, preferably between 0.5 hours and 14 days, in particular between 1 hour and 7 days, or between 1.5 hours and 5 days, more preferably between 2 hours and 1 day. In the two-component mixtures and compositions according to the invention, the weight ratio of components 1) and 2) generally depends on the characteristics of the active ingredients used and is usually in the range of 1:1000 to 1000:1, often in the range of 1:100 to 100:1, usually in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1, even more preferably in the range of 1:4 to 4:1, in particular in the range of 1:2 to 2:1.

[0191] According to further embodiments of the two-component mixtures and compositions thereof, the weight ratio of component 1) to component 2) is usually in the range of 1000:1 to 1:1000, often in the range of 100:1 to 1:100, usually in the range of 50:1 to 1:50, preferably in the range of 20:1 to 1:20, more preferably in the range of 10:1 to 1:10, even more preferably in the range of 4:1 to 1:4, in particular in the range of 2:1 to 1:2.

[0192] In the compositions of the invention comprising a ternary mixture, i.e. (component 1 and component 2) and compound III (component 3), the weight ratio of components 1) to 2) depends on the properties of the active substances used. It is usually in the range of 1:100-100:1, often in the range of 1:50-50:1, preferably in the range of 1:20-20:1, more preferably in the range of 1:10-10:1, in particular in the range of 1:4-4:1, and the weight ratio of components 1) to 3) is usually in the range of 1:100-100:1, often in the range of 1:50-50:1, more preferably in the range of 1:20-20:1, more preferably in the range of 1:10-10:1, in particular in the range of 1:4-4:1.

[0193] Any further active ingredients are optionally added in a ratio of 20:1 to 1:20 relative to component 1).

[0194] These rates are also suitable for mixtures of the invention applied by seed treatment.

[0195] In one embodiment, the individual components of the composition according to the invention, such as parts of a kit or parts of a two- or three-component mixture, can be mixed by the user himself in a spray tank or any other type of container used for application (e.g., seed treatment drum, seed pelletizer, knapsack sprayer).Further adjuvants can be added, if necessary.

[0196] Thus, one embodiment of the present invention is a kit for preparing a ready-to-use agrochemical composition comprising: a) a composition comprising component 1) as defined herein and at least one adjuvant; and b) a composition comprising component 2) as defined herein and at least one adjuvant; and optionally c) a composition comprising at least one adjuvant and optionally a further active ingredient 3) as defined herein.

[0197] The application of the compounds of formula (I), their combinations and compositions can be carried out before or during sowing. The methods of applying the compounds of formula (I), their combinations and compositions, respectively, are application to plant propagation materials, particularly seeds, including dressing, coating, pelleting, spraying, and dipping, as well as in-furrow application methods.

[0198] Preferably, the compounds of formula (I), combinations and compositions thereof are applied to the plant propagation material in a manner such that germination is not induced, for example by seed dressing, pelleting, coating and dusting, respectively.

[0199] The compounds of formula (I) may also be used as fungicides. As used herein, the term "fungicide" refers to a compound that inhibits, modifies, or prevents the growth of plant pathogenic fungi.

[0200] The compounds of formula (I), their combinations and compositions, respectively, can be used to improve plant health. The present invention also relates to a method of improving plant health by treating the plant, its propagation material and / or the locus where the plant is growing or to be grown, respectively, with an effective amount of at least one compound of formula (I) and / or its composition.

[0201] In one embodiment, the present invention provides a method for suppressing or preventing plant infestation by phytopathogenic microorganisms in agricultural and / or horticultural crops, comprising applying an effective amount of at least one compound of formula (I) or a combination or composition thereof to the plant, part thereof or the locus thereof.

[0202] In another embodiment, the present invention provides a method for suppressing or preventing plant infestation by plant pathogenic microorganisms in agricultural and / or horticultural crops, wherein an effective amount of a compound of formula (I) or a combination or composition thereof is applied to the seeds of the plants.

[0203] The compounds of formula (I) and the compositions of the present invention are suitable as fungicides, respectively. They are characterized by their remarkable effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, especially from the classes Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. Fungi imperfecti). Some are systemically active and can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. Furthermore, they are particularly suitable for controlling harmful fungi that occur in wood or plant roots.

[0204] The compounds of formula (I) and compositions of the invention are particularly important in the control of a large number of phytopathogenic fungi in various cultivated plants, examples of which include cereals, such as wheat, rye, barley, triticale, oats, rice; beets, such as sugar beet or fodder beet; fruits, such as pomes, stone fruits, soft fruits, such as apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries, gooseberries; legumes, such as lentils, peas, alfalfa, soybeans; rapeseed, mustard, olives, sunflowers, coconuts, cocoa. oleaginous plants such as beans, castor oil, oil palm, ground berries and soybeans; cucurbits such as pumpkin, cucumber and melon; fibre plants such as cotton, flax, hemp and jute; citrus fruits such as oranges, lemons, grapefruit and mandarins; vegetables such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, cucurbits and peppers; evergreen broad-leaved plants such as avocado, cinnamon and camphor; energy and raw material plants such as corn, soybeans, rapeseed, sugarcane and oil palm; corn; tobacco; nuts; coffee; tea; bananas; grapes (table grapes and grape vines for grape juice); hops; grass; sweet leaf (also known as stevia); ornamental and forestry plants such as rubber plants or flowers, shrubs, broad-leaved trees and evergreen trees, e.g. conifers; and plant propagation material such as seeds and crop material of these plants; etc. In particular, the compounds and compositions of formula (I) of the present invention are important for controlling phytopathogenic fungi in plant propagation material such as soybeans and seeds and in crop material of these plants.

[0205] Preferably, the compounds of formula (I) and compositions thereof are used for controlling a large number of fungi on field crop fruits such as potato, sugar beet, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybean, rapeseed, beans, sunflower, coffee or sugarcane; grapes; ornamentals; or vegetables such as cucumber, tomato, bean, pumpkin, respectively.

[0206] The term "plant propagation material" should be understood to refer to all reproductive parts of a plant, such as seeds and cuttings and vegetative plant material, such as tubers (e.g., potatoes), that can be used to propagate a plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts, twigs, flowers, and other parts of a plant, including seedlings and young plants that are transplanted after germination or emergence from the soil.

[0207] These young plants can also be protected before transplanting by total or local treatment by immersion or pouring.

[0208] Preferably, treatment of plant propagation material with a compound of formula (I), combinations thereof and / or compositions is used to control a number of fungi on cereals such as wheat, rye, barley and oats, on rice, corn, cotton and soybean, respectively.

[0209] The term "cultivated plants" should be understood to include plants modified by breeding, mutagenesis or genetic engineering, including but not limited to agricultural biotechnology products on the market or in development (see: http: / / cera-gmc.org / GM crop database). Genetically modified plants are plants whose genetic material has been modified by recombinant DNA techniques and is not readily obtainable by crossing, mutation, or natural recombination in a natural environment. Typically, one or more genes are incorporated into the genetic material of a genetically modified plant to improve certain plant characteristics. Such genetic modifications also include, but are not limited to, targeted post-translational modifications of proteins, oligo- or polypeptides, such as modifications by glycosylation or polymer addition (such as prenylated, acetylated, or farnesylated moieties, or PEG moieties). Plants that have been modified by breeding, mutagenesis, genetic engineering, etc. to tolerate the use of specific classes of herbicides, such as auxinic herbicides such as dicamba and 2,4-D; bleach herbicides such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors and phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonylureas and imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors such as glyphosate; glutamine synthase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl-CoA carboxylase (ACCase) inhibitors; and oxynil (i.e. bromoxynil or ioxynil) herbicides, are in use as a result of conventional breeding or genetic engineering. Additionally, plants have been engineered to tolerate multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate, or to both glyphosate and another class of herbicide, such as ALS inhibitors, HPPD inhibitors, auxinic herbicides, or ACCase inhibitors.These herbicide resistance techniques are described, for example, in Pest Managem. Sci. 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1 185; and references cited therein. Some cultivated plants have been made resistant to herbicides by traditional breeding methods (mutagenesis), for example Clearfield® summer rape (Canola, BASF SE, Germany) to imidazolinones, imazamox or ExpressSun® sunflowers (DuPont, USA) to sulfonylureas such as tribenuron. Genetic engineering techniques have been used to make cultivated plants such as soybean, cotton, corn, beet and rapeseed resistant to herbicides such as glyphosate and glufosinate. Some of these are commercially available under the trade names RoundupReady® (glyphosate-resistant, Monsanto, USA), Cultivance® (imidazolinone-resistant, BASF SE, Germany) and LibertyLink® (glufosinate-resistant, Bayer CropScience, Germany).

[0210] Furthermore, within the scope of the invention are plants which, by the use of recombinant DNA techniques, are able to synthesize one or more insecticidal proteins known in particular from the bacterial genus Bacillus, such as δ-endotoxins, in particular from Bacillus thuringiensis, such as CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl) or Cry9c; multiplicative insecticidal proteins (VIPs), such as VIP1, VIP2, VIP3; insecticidal proteins of bacteria colonizing nematodes, such as Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion venom, spider venom, wasp venom and other insect-specific neurotoxins; toxins produced by fungi such as Streptomyces toxins, plant lectins such as pea and barley lectins; agglutinins; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome-inactivating proteins (RIPs) such as ricin, maize-RIP, abrin, rufin, saporin, bryodin; steroid metabolism enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyltransferase, cholesterol oxidase, ecdysone inhibitor, HMG-CoA reductase; ion channel blockers such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinase or glucanase, etc. In the context of the present invention, these insecticidal proteins or toxins are also to be explicitly understood as pretoxins, hybrid proteins, truncated proteins or modified proteins. Hybrid proteins are characterized by novel combinations of protein domains (see, for example, WO02 / 015701). Further examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in EP374753, WO93 / 007278, WO95 / 34656, EP427529, EP451878, WO03 / 18810 and WO03 / 52073.Methods for producing such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. These insecticidal proteins contained in transgenic plants confer resistance to harmful pests from all taxa of arthropods, in particular beetles (Coleoptera), dipterans (Diptera), moths (Lepidoptera), and nematodes (Nematoda), by producing these proteins.Transgenic plants capable of synthesizing one or more insecticidal proteins are described, for example, in the above publications, some of which are commercially available, such as YieldGard® (a maize cultivar producing the CrylAb toxin), YieldGard® Plus (a maize cultivar producing the CrylAb and Cry3Bb1 toxins), Starlink® (a maize cultivar producing the Cry9c toxin), Herculex® RW (a maize cultivar producing Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin-N-acetyltransferase [PAT]); NuCOTN® 33B (a cotton cultivar producing the CrylAc toxin), Bollgard® I (a cotton cultivar producing the Cry1 Ac toxin), Bollgard® II (a cotton cultivar producing the CrylAc and Cry2Ab2 toxins); VIPCOT® (a cotton cultivar producing a VIP toxin); NewLeaf® (a potato cultivar producing a Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta PAT, Bt1 1 (e.g., Agrisure® CB) and Bt176 (a maize cultivar producing a CrylAb toxin and a PAT enzyme) from Syngenta Seeds SAS, France, MIR604 (a maize cultivar producing a modified form of the Cry3A toxin, see WO 03 / 018810) from Syngenta Seeds SAS, France, MON 863 (a maize cultivar producing a Cry3Bb1 toxin) from Monsanto Europe SA, Belgium, IPC 531 (a cotton cultivar producing a modified version of the CrylAc toxin) from Monsanto Europe SA, Belgium and 1507 from Pioneer Overseas Corporation, Belgium. (a maize cultivar that produces Cry1 F toxin and PAT enzyme).

[0211] Furthermore, plants capable of synthesizing one or more proteins for increased resistance or tolerance to bacterial, viral or fungal pathogens by the use of recombinant DNA techniques are also within the scope of the present invention. Examples of such proteins are so-called "pathogenesis-related proteins" (PR proteins, see for example EP 392225), plant disease resistance genes (for example potato cultivars expressing a gene for resistance to Phytophthora infestans from the Mexican wild potato Solanum bulbocastanum) or T4-lysozyme (for example potato cultivars capable of synthesizing these proteins with increased resistance to bacteria such as Erwinia amylvora). Methods for producing such genetically modified plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above.

[0212] Additionally, plants which, through the use of recombinant DNA techniques, can be made to synthesize one or more proteins to enhance productivity (e.g., biomass production, grain yield, starch content, oil content, protein content), resistance to drought, salinity or other growth-limiting environmental factors, or resistance of those plants to pests and fungal, bacterial or viral pathogens, are within the scope of the present invention.

[0213] Additionally, plants that contain altered amounts of or new substances through the use of recombinant DNA technology to improve human or animal nutrition are also within the scope of the invention, for example oil crops producing health-promoting long-chain omega-3 or unsaturated omega-9 fatty acids (e.g., Nexera® rape (DOW Agro Sciences, Canada)).

[0214] Additionally, plants that have altered amounts of content substances or contain new content substances through the use of recombinant DNA technology to improve raw material production, such as potatoes with increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany), are also within the scope of the present invention.

[0215] The compounds of formula (I) may be effective against, for example, disease fungi and fungal vectors as well as phytopathogenic bacteria and viruses, such as, for example: Absidia corymbifera, Alternaria spp, Aphanomyces spp, Ascochyta spp, and Aspergillus spp.: A. flavus. fumigatus、A. nidulans、A. niger、A. terms Aureobasidium spp.: A. pullulans, Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, and Botryosphaeria spp.: B. dothidea. obtusa, one and two Botrytis spp.: B. cinerea, one and two Candida spp.: C. albicans, C. obtusa. glabrata、C. krusei、C. lusitaniae、C. parapsilosis、C. tropicalis spp, including Colletotrichum spp.: C. musae, Cryptococcus neoformans, Colletotrichum capsici, Diaporthe spp, Didymella spp, Drechslera spp, Elsinoe spp, Epidermophyton spp, and Erwinia amylovora, among Erysiphe spp.: E. cichoracearum, Eutypa lata, among Fusarium spp.: F. culmorum, F. culmorum. graminearum、F. langsethiae、F. moniliform、F. oxysporum、F. proliferatum、F. subglutinans、F.solani, Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, Helminthosporium spp, Hemileia spp, Histoplasma spp. including: H. capsulatum, Laetisaria fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, Fusarium culmorum, Gibberella zeae (Fusarium graminearum), Mycosphaerella arachidis (Cercospora arachidicola), Pyrenophora teres, Blumeria graminis f. sp. tritici (Erysiphe graminis f. sp. tritici), Microdochium nivale, Microsporum spp, Monilinia spp, Mucor spp, Mycosphaerella spp. including: M. graminicola, M. pomi、Oncobasidium theobromaeon、Ophiostoma piceae、Paracoccidioides spp、the following includes Penicillium spp.: P. digitatum、P. italicum、Petriellidium spp、the following including Peronosclerospora spp.: P. maydis、P. philippinensis and P.sorghi. Peronospora spp. Parastagonospora nodorum Phaeosphaeria nodorum. Phakopsora pachyrhizi spp.: P. infestans.Plasmopara spp.: P. halstedii.P. viticola, Pleospora spp., and Podosphaera spp.: P. leucotricha, Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp., and Pseudoperonospora spp.: P. cubensis. humuli, Pseudopeziza tracheiphila, and Puccinia spp.: P. hordei. recondite、P. striiformis、P. triticina Pyrenopeziza spp Pyrenophora spp Pyricularia spp: P. oryzae Pythium spp: P. ultimum Ramularia spp Rhizoctonia spp. Rhizomucor pusillus Rhizopus arrhizus Rhynchosporium spp. Scedosporium spp.: S. apiospermum. prolificans, Schizothyrium pomi, Sclerotinia spp, Sclerotium spp, and Septoria spp: S. nodorum. tritici, Septoria lycopersici, Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp, Stagonospora nodorum, Stemphylium spp., Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilletia spp, Trichoderma spp. including: T. harzianum, T. pseudokoningii, T. viride, Trichophyton spp, Typhula spp, Uncinula necator, Urocystis spp, Ustilago spp. including: V. inaequalis, Verticillium spp., and Xanthomonas spp, Ustilaginales, such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, Ustilago zeae, Cerotelium fici, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, Puccinia graminis, Puccinia sorghi, Puccinia striiformis f.sp. Hordei, Puccinia striiformis f.sp. Secalis, Pucciniastrum coryli, or Uredinales, such as Cronartium ribicola, Gymnosporangium juniperi-viginianae, Melampsora medusae, Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor and Uromyces viciae-fabae, Cryptococcus spp., Exobasidium vexans, Marasmiellus inoderma, Mycena spp., Sphacelotheca reiliana, Typhula ishikariensis, Urocystis agropyri, ltersonilia perplexans, Corticium invisum, Waitea circinata, Rhizoctonia solani, Thanetephorus cucurmeris, Entyloma dahliae, Entylomella microspora, Neovossia moliniae and Tilletia caries, Blastocladiomycetes, such as Physoderma maydis, Mucoromycetes, such as Choanephora cucurbitarum. .

[0216] Non-limiting examples of fungal disease pathogens that can be treated according to the present invention include diseases caused by rust pathogens, such as Gymnosporangium species, such as Gymnosporangium sabinae; Hemileia species, such as Hemileia vastatrix; Phakopsora species, such as Phakopsora pachyrhizi or Phakopsora meibomiae; Puccinia species, such as Puccinia recondita, Puccinia graminis or Puccinia striiformis; Uromyces species, such as Uromyces appendiculatus.

[0217] In particular, Cronartium ribicola (white resin rust); Gymnosporangium juniperi-virginianae (cedar apple rust); Hemileia vastatrix (coffee rust); Phakopsora meibomiae and P. pachyrhizi (soybean rust); Puccinia coronata (crown rust of oats and ryegrass); Puccinia graminis (stem rust of wheat, Kentucky bluegrass, black rust of cereals); Puccinia hemerocallidis (lily rust); Puccinia persistens subsp. triticina (wheat rust or "brown or red rust"); corn rust; Puccinia striiformis ("yellow rust"); Uromyces appendiculatus (bean rust); Uromyces phaseoli (bean rust); Puccinia melanocephala (sugarcane "brown rust"); Puccinia kuehnii ('orange rust' of sugarcane).

[0218] The present invention further relates to the use of a compound of formula (I), a combination or a composition thereof for the control or prevention of phytopathogenic fungi such as Septoria, powdery mildew, Botrytis cinerea, Anthracnose, Alternaria, Scab and Monilinia in agricultural and / or horticultural crops.

[0219] The present invention further relates to the use of the compounds of formula (I), combinations or compositions thereof for the control or prevention against phytopathogenic fungi such as Septoria, powdery mildew, gray mold, leaf spot diseases like anthracnose, Alternaria, apple scab, Cercospora, Corynespora and Monilinia in cereals, soybeans, grapes, fruits, nuts and vegetables.

[0220] Plants which can be treated according to the invention include cotton, flax, grapes, fruits, vegetables, such as Rosaceae (e.g. apple, pear, apricot, cherry, almond, peach, etc.), Libeciaceae, Juglandaceae, Birch, Anacardiaceae, Fagaceae, Mulberry, Oleaceae, Actinidiaceae, Lauraceae, Musaceae (e.g. banana trees and plantations), Rubiaceae (e.g. coffee), Hirundinaceae, Stercheraceae, Rutaceae (e.g. lemon, orange, grapefruit); Vitaceae (e.g. grapes); Solanaceae (e.g. tomatoes, peppers), Liliaceae, Asteraceae (e.g. lettuce), Apiaceae, Brassicaceae, Chenopodiaceae, Cucurbitaceae. (e.g. cucumber), Alliaceae (e.g. leeks, onions), Papilionaceae (e.g. peas); staple crops such as Poaceae / Gramineae (e.g. cereals such as maize, grass, wheat, rye, rice, barley, oats, millet, triticale), Asteraceae (e.g. sunflower), Brassicaceae (e.g. Chinese cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radish, rapeseed, mustard, horseradish, cress), Legumes (e.g. beans, peanuts), Fabaceae (e.g. soybean), Solanaceae (e.g. potato), Chenopodiaceae (e.g. sugar beet, beetroot, Swiss chard, beetroot); Malvaceae (e.g. cotton); useful and ornamental plants for gardens and woodlands; and genetically modified varieties of these plants.

[0221] More preferably, it is applied to control the following soybean diseases occurring on soybean leaves, stems, pods and seeds, such as Altemaria spec. atrans tenuissima, Colletotrichum gloeosporoides dematium var. truncatum, Septoria glycines, Cercospora kikuchii leaf spot and late blight, Choanephora infundibulifera trispora (Syn.), Dactuliophora glycines, Peronospora manshurica, Drechslera glycini, Cercospora sojina, Leptosphaerulina leaf spot, and others. trifolii), Phyllosticta leaf spot (Phyllosticta sojaecola), pod stalk blight (Phomopsis sojae), powdery mildew (Microsphaera diffusa), pyrenochaeta leaf spot (Pyrenochaeta glycines), rhizome blight (Rhizoctonia solani), rust (Phakopsora pachyrhizi, Phakopsora meibomiae), scab (Sphaceloma glycines), stem blight (Stemphylium botryosum), and target blight (Corynespora cassiicola).

[0222] Fungal diseases occurring at the base of the roots and stems, such as black root rot, charcoal rot (Macrophomina phaseolina), rot wilt, root rot, pod and stem rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti, Fusarium culmorum), net spot (Pyrenophora teres), powdery mildew (Blumeria graminis f. sp. Tritici), leaf spot (Cercospora arachidicola), rot wilt (Gibberella zeae), root rot of Mycoleptodiscus (Mycoleptodiscus terrestris), neocosmospora (Neocosmospora vasinfecta), pod and stem rot (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var caulivora), Phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregata), Pythium rot (Pythium aphanidennatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia root, stem and damping off (Rhizoctonia solani), Sclerotinia stem rot (Sclerotinia sclerotiorum), Sclerotinia southern blight (Sclerotinia rolfsii), and Thielaviopsis root rot (Thielaviopsis basicola).

[0223] The present invention also relates to the use of a compound of formula (I), a combination or a composition thereof for the control or prevention of the following plant diseases: Puccinia spp. (rusts) in various plants, such as, but not limited to, P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) in cereals such as wheat, barley or rye, and Phakopsoraceae spp. in various plants, in particular Phakopsora pachyrhizi and P. meibomiae (soybean rust) in soybeans, Hemileia vastatrix (coffee rust), Uromyces appendiculatus, Uromyces fabae, and Uromyces phaseoli (bean rust).

[0224] The compounds, combinations and compositions of the present invention can be used to control or prevent plant diseases. The compounds of formula (I), combinations and / or compositions, respectively, are particularly suitable for controlling the following plant diseases: Albugo spp. (white rust) occurs on ornamental plants, plants (e.g. A. candida) and sunflowers (e.g. A. tragopogonis); Alternaria spp. (alternaria leaf spot) occurs on plants, rapeseed (A. brassicola or A. brassicae), sugar beet (A. tenuis), fruit, rice, soybean, potato (e.g. A. solani or A. alternata), tomato (e.g. A. solani or A. alternata) and wheat; Aphanomyces spp. occurs on sugar beet and plants; Ascochyta spp. occurs on cereals and plants, e.g. A. tritici (anthracnose) occurs on wheat and A. hordei occurs on barley; Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), e.g. southern leaf blight (D. maydis) or northern leaf blight (B. zeicola): occurs on corn, e.g. spot blight (C. sorokiniana): occurs on cereals, and e.g. B. oryzae: occurs on rice and turf; Blumeria (formerly Erysiphe) graminis (powdery mildew): occurs on cereals (e.g. wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: grey mold): occurs on fruits and berries (e.g. strawberries), plants (e.g. lettuce, carrots, celery and cabbage), rapeseed, flowers, vines, forest plants and wheat; Bremia lactucae (downy mildew): occurs on lettuce; Ceratocystis (syn. Ophiostoma) spp. (rot or dieback disease): broad-leaved and evergreen trees, e.g. C. ulmi (Dutch elm disease): occurs on elms; Cercospora spp. (Cercospora leaf spot disease): occurs on corn (e.g. grey leaf spot disease: C. zeae-maydis), rice, sugar beet (e.g. C. beticola), sugar cane, plants, coffee, soybean (e.g. C. sojina or C. kikuchii) and rice; Cladosporium spp.: occurs on tomatoes (e.g. C. fulvum: leaf mold) and cereals, e.g. C.herbarum (wheat rot): occurs on wheat; Claviceps purpurea (ergot): occurs on cereals; Cochliobolus (anamorph: Helminthosporium of Bipolaris) spp. (leaf spot disease): occurs on corn (C. carbonum), cereals (e.g., C. sativus, anamorph: B. sorokiniana) and rice (e.g., C. miyabeanus, anamorph: H. oryzae); Colletotrichum (teleomorph: Glomerella) spp. (anthracnose): occurs on cotton (e.g., C. gossypii), corn (e.g., C. graminicola: anthracnose stem rot disease), soft fruits, potatoes (e.g., C. coccodes: black spot), beans (e.g., C. lindemuthianum) and soybeans (e.g., C. truncatum or C. gloeosporioides); Corticium spp., e.g., C. sasakii (sheath blight): occurs on rice; Corynespora cassiicola (target spot): occurs on soybeans and ornamental plants; Cycloconium spp., e.g., C. oleaginum: occurs on olive trees; Cylindrocarpon spp. (e.g., fruit canker or grapevine decline, teleomorph: Nectria or Neonectria spp.): occurs on fruit trees, vines (e.g., C. liriodendri, teleomorph: Neonectria liriodendri: black leg disease) and ornamental plants; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot): occurs on soybeans; Diaporthe spp., e.g., D. phaseolorum (rot disease), occurring on soybeans; Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp., occurring on maize, cereals, e.g., barley (e.g., D. teres, net blotch disease) and wheat (e.g., D. tritici-repentis, tan spot disease), rice and turf; Esca (canker disease, apoplexy), occurring on vines, Formitiporia (syn. Phellinus) punctata, F.mediterranea, Phaeomoniella chlamydospora (formerly Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and / or Botryosphaeria obtusa; Elsinoe spp. on pome fruits (E. pyri), soft fruits (E. veneta) and vines (E. ampelina); Entyloma oryzae (leaf mildew) on rice; Epicoccum spp. (black mold) on wheat; Erysiphe spp. (powdery mildew) on sugar beet (E. betae), plants (e.g. E. pisi), e.g. gourd (e.g. E. cichoracearum), cabbage, rapeseed (e.g. E. cruciferarum); Eutypa lata (vine wilt or blight of Eucheuma, anamorph: Cytosporina lata, syn. Libertella blepharis) occurring on fruit trees, vines and ornamental wood; Exserohilum (syn. Helminthosporium) spp. occurring on corn (e.g. E. turcicum); Fusarium (teleomorph: Gibberella) spp. (damp, root or stem rot) occurring on various plants, e.g. F. graminearum or F. culmorum (root rot, scab or blight) occurring on cereals (e.g. wheat or barley), F. oxysporum on tomato, F. solani (f.sp. glycines, now syn. F. virguliforme) as well as F. tucumaniae and F. brasiliense causing sudden death syndrome on soybean, respectively, and F. verticillioides on corn; Gaeumannomyces graminis (damage) on cereals (e.g., wheat or barley) and corn; Gibberella spp. (e.g., G. zeae) and rice (e.g., G. fujikuroi: bakanae disease); Glomerella cingulata (damage) on vines, pome fruits and other plants, and G.gossypii: occurs on cotton; grain stain complex: occurs on rice; Guignardia bidwellii (black rot): occurs on vines; Gymnosporangium spp.: occurs on roses and junipers, e.g., G. sabinae (rust): occurs on pears; Helminthosporium spp. (syn. Drechslera, teleomorph: Cochliobolus): occurs on corn, cereals and rice; Hemileia spp., e.g., H. vastatrix (coffee leaf rust): occurs on coffee; Isariopsis clavispora (syn. Cladosporium vitis): occurs on vines; Macrophomina phaseolina (syn. phaseoli) (root and stem rot) on soybeans and cotton;Microdochium (syn. Fusarium) nivale (pink snow rot) on cereals (e.g. wheat or barley);Microsphaera diffusa (powdery mildew) on soybeans;Monilinia spp., e.g. M. laxa, M. fructicola and M. fructigena (flower and twig blight, brown rot) on stone fruits and other Rosaceae plants;Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, e.g. M. graminicola (anamorph: Septoria tritici, Septoria leaf blight) on wheat or M. fijiensis (black Sigatoka) on bananas;Peronospora spp. (downy mildew): occurs on cabbage (e.g. P. brassicae), rapeseed (e.g. P. parasitica), onion (e.g. P. destructor), tobacco (P. tabacina) and soybean (e.g. P. manshurica); Phakopsora pachyrhizi and P. meibomiae (soybean rust): occurs on soybean; Phialophora spp.: occurs for example on vines (e.g. P. tracheiphila and P. tetraspora) and soybean (e.g. P. gregata: stem rot); Phoma lingam (root and stem rot): occurs on rapeseed and cabbage, and P.betae (root rot, leaf spot and rot) on sugar beet; Phomopsis spp. on sunflower, vines (e.g. P. viticola: stem and leaf spot) and soybean (e.g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spot) on corn; Phytophthora spp. (dampening, root, leaf, fruit and stem root) on various plants, e.g. pepper and gourd (e.g. P. capsici), soybean (e.g. P. megasperma, syn. P. sojae), soybean, potato and tomato (e.g. P. infestans: leaf spot) and broadleaf trees (e.g. P. ramorum: oak sudden death); Plasmodiophora brassicae (clubroot), occurring on cabbage, rapeseed, radish and other plants; Plasmopara spp., e.g. P. viticola (grape downy mildew), occurring on vines, and P. halstedii, occurring on sunflower; Podosphaera spp. (powdery mildew), occurring on roses, hops, pome and soft fruits, e.g. P. leucotricha, occurring on apple; Polymyxa spp., e.g. on cereals, e.g. barley and wheat (P. graminis) and sugar beet (P. betae), transmitting viral diseases; Pseudocercosporella herpotrichoides (eyespot, teleomorph: Tapesia yallundae): occurs on cereals, e.g., transmitted to wheat or barley;Pseudoperonospora (downy mildew): occurs on various plants, e.g., P. cubensis: on gourd or P. humili: on hops;Pseudopezicula tracheiphila (fireworks disease or Rotbrenner disease, anamorph: Phialophora): occurs on vines;Puccinia spp. (rusts): occurs on various plants, e.g., P. triticina (brown or leaf rust), P. striiformis (yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P.recondita (brown or leaf rust) on cereals, e.g., wheat, barley or rye; P. kuehnii (orange rust) on sugarcane and P. asparagi on asparagus; Pyrenophora (anamorph: Drechslera) tritici-repentis (yellow spot) on wheat or P. teres (net blotch) on barley; Pyricularia spp. on turf and cereals, e.g., P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals; Pythium spp. (rot) on turf, rice, corn, wheat, cotton, rapeseed, sunflower, soybean, sugar beet, plants and various other plants (e.g., P. ultimum or P. aphanidermatum); Ramularia spp., e.g. R.collo-cygni (ramularia leaf spot, physiological leaf spot): barley and R.beticola: occurs on sugar beet; Rhizoctonia spp.: cotton, rice, potato, turf, corn, rapeseed, potato, sugar beet, plants and various other plants, e.g. R.solani (root and stem rot): soybean, R.solani (sheath blight): rice or R.cerealis (Rhizoctonia spring blight): occurs on wheat or barley; Rhizopus stolonifer (black mold, soft rot): occurs on strawberry, carrot, cabbage, vines and tomatoes; Rhynchosporium secalis (scald): occurs on barley, rye and triticale; Sarocladium oryzae and S.attenuatum (sheath rot): occurs on rice; Sclerotinia spp. (stalk rot or white mold disease): occurs in plants and crops, e.g., rapeseed, sunflower (e.g., S. sclerotiorum) and soybean (e.g., S. rolfsii or S. sclerotiorum);Septoria spp.: occurs in various plants, e.g., S. glycines (brown spot disease): soybean, S. tritici (Septoria leaf blight): wheat and S. (syn. Stagonospora) nodorum (Stagonospora leaf blight): occurs in cereals;Uncinula (syn.Erysiphe) necator (powdery mildew, anamorph: Oidium tuckeri) on vines; Setospaeria spp. (leaf blight) on corn (e.g. S. turcicum, syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (sooty mildew) on corn, (e.g. S. reiliana: sooty mildew), sorghum and sugarcane; Sphaerotheca fuliginea (powdery mildew) on gourds; Spongospora subterranea (powdery mildew) on potatoes, and a viral disease transmitted by them; Stagonospora spp. on cereals, e.g. S. nodorum (stagonospora leaf blight, teleomorph: Leptosphaeria [syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato wart); Taphrina spp., e.g. T. deformans (leaf curl) on peaches and T. pruni (plum pocket) on plums; Thielaviopsis spp. (black root rot) on tobacco, pome fruits, plants, soybeans and cotton, e.g. T. basicola (syn. Chalara elegans); Tilletia spp. (common smut or smut) on cereals, e.g. T. tritici (syn. T. caries, wheat smut) and T. controversa (dwarf smut) on wheat; Typhula incarnata (grey snow rot) on barley or wheat; Urocystis spp., e.g. U. occulta (stem sooty) on rye; Uromyces spp. (rusts): occur on plants such as beans (e.g. U. appendiculatus, syn. U. phaseoli) and sugar beet (e.g. U. betae); Ustilago spp. (naked smut): occur on cereals (e.g. U. nuda and U. avaenae), maize (e.g. U. maydis: maize sooty mold) and sugar cane; Venturia spp. (fusarium leaf spot): occur on apples (e.g. V.inaequalis) and pear; and Verticillium spp. (damaging disease) on various plants, e.g. fruit and ornamental plants, vines, soft fruits, plants and field crops, e.g. V. dahliae on strawberry, rapeseed, potato and tomato.

[0225] In one embodiment, the compounds of formula (I) have broad spectrum activity against fungal pathogens. Examples of pathogens include, but are not limited to, wheat leaf blight (Zymoseptoria tritici), wheat leaf rust (Puccinia triticina), wheat stripe rust (Puccinia striiformis), apple scab (Venturia inaequalis), grape powdery mildew (Uncinula necator), barley scald (Rhynchosporium secalis), rice blast (Pyricularia oryzae), soybean rust (Phakopsora pachyrhizi), wheat leaf blight (Leptosphaeria nodorum), wheat powdery mildew (Blumeria graminis f. sp. tritici), barley powdery mildew (Blumeria graminis f. sp. hordei), cucumber powdery mildew (Erysiphe cichoracearum), cucumber anthracnose (Colletotrichum lagenarium), beet and soybean leaf spot (Cercospora beticola), early blight of tomato (Alternaria solani), barley disease (Cochliobolus sativus), grey mold (Botrytis cinerea), common ear rot (Fusarium culmorum), white mold (Sclerotinia sclerotiorum), pink snow mold (Microdochium nivale), head blight (Fusarium graminearum), take-all (Gaeumannomyces graminis), wheat leaf rust (Puccinia triticina), early leaf blight (Mycosphaerella arachidis), and net blotch (Pyrenophora teres).

[0226] The exact amount of active material to be applied depends not only on the specific active material to be applied, but also on the specific effect desired, the fungal species to be controlled and its growth stage, and the part of the plant or other product that comes into contact with the compound.Therefore, not all compounds and formulations that contain the compounds are equally effective at similar concentrations or against the same fungal species.

[0227] The compounds of formula (I), their combinations and compositions are suitable for controlling harmful fungi in the protection of stored products or harvests and in the protection of materials, respectively.The term "protection of materials" is understood to mean the protection of industrial materials and non-living materials, such as adhesives, glues, wood, paper and board, textiles, leather, paint dispersions, plastics, cooling lubricants, fibers or textiles, from the invasion and destruction of harmful microorganisms, such as fungi and bacteria.

[0228] With regard to the protection of wood and other materials, special attention is paid to the following harmful fungi: Ascomycetes, such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes, such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Pora spp., Serpula spp., and also Tyromyces spp., Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Altemaria spp., Paecilomyces spp. and Mucor spp. spp., and in the protection of stored products and harvest the following yeasts are noteworthy: Candida spp. and Saccharomyces cerevisae.

[0229] In one embodiment, the present invention provides a method for controlling or preventing phytopathogenic microorganisms, comprising treating the fungus or the material, plant, plant part, locus, soil or seed to be protected from fungal attack with at least one compound of formula (I) as defined in claim 1 or a combination or composition comprising at least one compound of formula (I).

[0230] The treatment method according to the invention can also be used in the field of protecting stored products or harvested products from fungal and microbial attack. According to the invention, the term "stored products" is understood to refer to natural substances of plant or animal origin and their processed forms, which have been taken from their natural life cycle and for which long-term protection is desired. Stored products of plants or parts thereof, such as stems, leaves, tubers, seeds, fruits or crop plants, such as grains, can be protected in the freshly harvested state or in processed forms such as drying, wetting, grinding, crushing, pressing or roasting, this treatment is also known as post-harvest treatment. Also included in the definition of stored products is wood, whether in the form of raw wood such as building timber, utility poles and barriers, or in the form of finished products such as furniture or objects made from wood. Stored products of animal origin are hides, leather, fur, hair, etc. The combination according to the invention can prevent adverse effects such as decay, discolouration or mould. Preferably, "stored products" is understood to refer to natural substances of plant origin and their processed forms, more preferably to fruits and their processed forms, such as pome, stone fruits, soft fruits and citrus fruits and their processed forms.

[0231] The treatment of plants and plant parts with the compounds of formula (I) is carried out by applying them directly or to their surroundings, habitats or storage spaces using conventional treatment methods, such as immersion, spraying, misting, irrigation, evaporation, scattering, spraying, spraying, foaming, spreading, application, injection, watering (immersion), drip irrigation, etc., and also in the case of propagation materials, especially seeds, by powders for dry seed treatment, solutions for liquid seed treatment, water-soluble powders for slurry treatment, covering, one or more coatings, etc. Furthermore, it is also possible to apply the compounds of formula (I) by the ultra-low volume method, or to inject the application form or the compounds of formula (I) themselves into the soil. A preferred direct treatment of plants is foliar application, i.e. the compounds of formula (I) are applied to the foliage, and the frequency of treatment and the application rate should be adjusted according to the infestation level of the disease in question.

[0232] In the case of systemically active compounds, the compound of formula (I) also gains access to the plant through the root system. The plant is then treated by the action of the compound of formula (I) on the plant habitat. This can be done, for example, by immersion or by mixing into the soil or nutrient solution, i.e. by impregnating the plant locus (e.g. soil or hydroponic system) with a liquid form of the compound of formula (I), or by soil application, i.e. by introducing the compound of formula (I) according to the invention in solid form (e.g. in the form of granules) into the plant locus, or by drip application (often also called "chemicalization"), i.e. by applying the compound of formula (I) according to the invention in liquid form from a surface or subsurface drip line over a period of time with various amounts of water at a defined position in the vicinity of the plant. In the case of rice crops, this can also be done by metering the compound of formula (I) in solid form (e.g. granular) into flooded rice fields.

[0233] The compounds of the present invention can be used in combination with models incorporated into computer programs for, for example, site-specific crop management, satellite agriculture, precision agriculture or precision agriculture. Such models support site-specific management of agricultural sites using data from various sources such as soil, weather, crops (e.g., type, growth stage, plant health), weeds (e.g., type, growth stage), disease, pests, nutrients, water, moisture, biomass, satellite data, yield, etc., with the aim of optimizing profitability, sustainability and environmental protection. In particular, such models help optimize agricultural decisions, control the accuracy of pesticide spraying, and record the work carried out.

[0234] As an example, if the model models a pest infestation and calculates that a threshold has been reached at which it is recommended to apply a compound of the present invention to the crop plant, the compound of the present invention can be applied to the crop plant according to an appropriate dosing method.

[0235] Commercially available systems that include agricultural models include, for example, FieldScripts™ from The Climate Corporation, Xarvio™ from BASF, and AGLogic™ from John Deere.

[0236] The compounds of the present invention can also be used in combination with smart spraying devices, such as spot spraying or precision spraying devices attached to or housed in agricultural vehicles, such as tractors, robots, helicopters, airplanes, unmanned aerial vehicles (UAVs), such as drones. Such devices usually include input sensors (such as cameras) and a processing unit configured to analyze input data and provide a decision based on the analysis of the input data to specifically and precisely apply the compounds of the present invention to crop plants (or weeds). The use of such smart spraying devices also usually requires a location system (e.g., GPS receiver) to localize the recorded data and guide or control the agricultural vehicle; a geographic information system (GIS) to represent the information on a clear map, and a suitable agricultural vehicle to perform the required agricultural activities, such as spraying.

[0237] The ranges or desired values ​​given herein may be expanded or modified without losing the effect sought, as will be apparent to one of ordinary skill in the art having access to the teachings herein.

[0238] The invention disclosed in this disclosure will now be described in detail with the help of non-limiting examples. EXAMPLES

[0239] Chemical Examples: Example 1: Preparation of 3-cyclopropyl-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile a) Step 1: Preparation of 5-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine To a stirred solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine (600 mg, 3.05 mmol) in dimethylformamide (20 mL), sodium hydride (183 mg, 4.57 mmol, 60% dispersion in mineral oil) was added at 0° C., and the resulting reaction mixture was stirred at 0° C. for 20 min. To this reaction mixture, methyl iodide (0.19 mL, 3.05 mmol) was added, and the reaction mixture was further stirred at 25° C. for 3 h. After completion of the reaction, the reaction mixture was quenched with saturated ammonium chloride (20 mL) and extracted with ethyl acetate (3×20 mL). The organic layer was washed with brine solution (20 mL), dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography to give 5-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine (400 mg, 1.9 mmol, 62% yield). 1 H-NMR (400 MHz, DMSO-d6) δ 8.32-8.42 (m, 1H), 8.21 (d, J = 2.2 Hz, 1H), 7.59 (t, J = 3.7 Hz, 1H), 6.46 (d, J = 3.4 Hz, 1H), 3.64-3.82 (m, 3H).

[0240] b) Step 2: Preparation of 1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile 5-Bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine (1.0 g, 4.74 mmol), zinc cyanide (1.11 g, 9.48 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.22 g, 0.24 mmol) and 2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl (0.12 g, 0.24 mmol) were taken in dimethylformamide (10 mL) / water (0.5 mL). The resulting reaction mixture was heated at 150° C. for 1 h. After completion of the reaction, the reaction mixture was quenched with water (20 mL) and extracted with ethyl acetate (3×30 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography to give 1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (500 mg, 3.18 mmol, 67% yield). 1 H-NMR (400 MHz, DMSO-d6) δ 8.64 (d, J = 2.0 Hz, 1H), 8.51 (d, J = 2.0 Hz, 1H), 7.71-7.75 (m, 1H), 6.63 (d, J = 3.7 Hz, 1H), 3.85 (s, 3H); ESI MS (m / z) 158.10 (MH) + .

[0241] c) Step 3: Preparation of 3-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile To a stirred solution of 1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (5.0 g, 31.8 mmol) in dichloromethane (50 mL), N-bromosuccinimide (6.23 g, 35.0 mmol) was added under nitrogen atmosphere, and the resulting reaction mixture was stirred at 25° C. for 1 h. After completion of the reaction, the reaction mixture was added to water (100 mL), extracted with ethyl acetate (3×100 mL), dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography to give 3-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (6.9 g, 29.2 mmol, 92% yield). 1 H-NMR (400 MHz, CDCl3) δ 8.59-8.55 (m, 1H), 8.14 (d, J = 2.0 Hz, 1H), 7.37 (s, 1H), 3.90 (s, 3H).

[0242] d) Step 4: Preparation of 3-cyclopropyl-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile To a stirred solution of 3-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (2.5 g, 10.59 mmol) in toluene (25 mL), sodium carbonate (3.37 g, 31.8 mmol) was added at 25° C. and purged with nitrogen for 20 minutes. The resulting reaction mixture was stirred at 100° C. for 5 hours. After completion of the reaction, the reaction mixture was added to water (100 mL) and ethyl acetate (100 mL) and filtered. The organic layer was separated, dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography to give 3-cyclopropyl-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (1.7 g, 8.62 mmol, 81% yield). 1H-NMR (400 MHz, CDCl3) δ 8.54 (d, J = 2.0 Hz, 1H), 8.25 (d, J = 2.0 Hz, 1H), 7.00 (d, J = 0.7 Hz, 1H), 3.84 (s, 3H), 1.91-1.87 (m, 1H), 0.96-0.91 (m, 2H), 0.64-0.61 (m, 2H).

[0243] Example 2: Preparation of 3-chloro-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile To a stirred solution of 1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (2.5 g, 15.9 mmol) in dichloromethane (50 mL) was added N-chlorosuccinimide (2.13 g, 15.9 mmol) at 25° C. under nitrogen atmosphere and the reaction mixture was stirred at 25° C. for 6 h. After completion of the reaction, the reaction mixture was poured into water (100 mL). The crude product was extracted with ethyl acetate (3×100 mL), dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography to give 3-chloro-1-methyl-1H-pyro[2,3-b]pyridine-5-carbonitrile (2.5 g, 13.0 mmol, 82% yield). 1 H-NMR (400 MHz, CDCl3) δ 8.59 (d, J = 2.0 Hz, 1H), 8.21 (d, J = 2.0 Hz, 1H), 7.31 (s, 1H), 3.91 (s, 3H); ESI MS (m / z) 191.95 (MH) + .

[0244] Example 3: Preparation of 1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid To a stirred solution of 1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (0.5 g, 3.18 mmol) in acetic acid (10 mL) was added sulfuric acid (1.696 mL, 31.8 mmol) slowly at 25 °C. The resulting reaction mixture was stirred at 100 °C for 4 h. After completion of the reaction, acetic acid was evaporated from the reaction mixture to obtain a crude solid product. The resulting crude product was washed with hexane (20 mL) to obtain 1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (0.55 g, 3.12 mmol, 98% yield). 1 H-NMR (400 MHz, DMSO-d6) δ 8.80 (d, J = 2.0 Hz, 1H), 8.53 (d, J = 2.0 Hz, 1H), 7.64 (d, J = 3.4 Hz, 1H), 6.62 (d, J = 3.4 Hz, 1H), 3.85 (s, 3H); ESI MS (m / z) 176.95.

[0245] Example 4: Preparation of 2-oxo-2,3-dihydrooxazolo[4,5-b]pyridine-6-carboxylic acid a) Step 1: Preparation of methyl 2-oxo-2,3-dihydrooxazolo[4,5-b]pyridine-6-carboxylate To a stirred solution of methyl 6-amino-5-hydroxynicotinate (1 g, 5.95 mmol) in dimethylformamide (10 mL) was added 1,1-carbonyldiimidazole (1.45 g, 8.92 mmol) at 25° C. under inert atmosphere and heated at 80° C. for 2 h. After completion of the reaction, the reaction mixture was cooled and dimethylformamide was evaporated under reduced pressure. The residue was acidified with 1 N hydrochloric acid to give a brown precipitate. The solid material was filtered, washed with water (20 mL) and dried under reduced pressure to give methyl 2-oxo-2,3-dihydrooxazolo[4,5-b]pyridine-6-carboxylate (1.1 g, 5.67 mmol, 95% yield). 1 H-NMR (400 MHz, CDCl3) δ 8.86 (d, J = 1.7 Hz, 1H), 8.03 (d, J = 1.7 Hz, 1H), 3.97 (s, 3H).

[0246] b) Step 2: Preparation of 2-oxo-2,3-dihydrooxazolo[4,5-b]pyridine-6-carboxylic acid To a stirred solution of methyl 2-oxo-2,3-dihydrooxazolo[4,5-b]pyridine-6-carboxylate (1.1 g, 5.67 mmol) in methanol (20 mL) and water (2 mL), lithium hydroxide (0.41 g, 17 mmol) was added at 25° C., and the resulting reaction mixture was stirred at 75° C. for 2 h. After completion of the reaction, the reaction mixture was cooled and methanol was evaporated under reduced pressure to obtain a residue. The resulting residue was neutralized with 10 N hydrochloric acid to obtain a precipitate. The solid was filtered, washed with water (20 mL), and dried under reduced pressure to obtain 2-oxo-2,3-dihydrooxazolo[4,5-b]pyridine-6-carboxylic acid (0.88 g, 4.86 mmol, 86% yield) as an off-white solid. 1 H-NMR (400 MHz, DMSO-d6) δ 13.15-12.90 (bs, 2H), 8.61 (d, J = 1.7 Hz, 1H), 7.96 (d, J = 1.7 Hz, 1H).

[0247] Example 5: Preparation of 2-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxylic acid a) Step 1: Preparation of 2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxylic acid To a stirred solution of phosphorus oxychloride (42.9 mL, 460 mmol) was added 2-oxo-2,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carboxylic acid (5.50 g, 30.7 mmol) at 25° C. The resulting reaction mixture was stirred at 110° C. for 5 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure and diluted with water (50 mL). The aqueous layer was extracted with ethyl acetate (3×200 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated and purified by column chromatography to give 2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxylic acid (2.180 g, 11.03 mmol, 36% yield). 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.14 (s, 1H), 3.09 (t, J = 7.8 Hz, 2H), 3.03 (d, J = 7.6 Hz, 0H), 2.99 (t, J = 7.3 Hz, 2H), 2.27-2.14 (m, 2H); MS (m / z) 197.85 (MH) + .

[0248] b) Step 2: Preparation of 2-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxylic acid To a stirred solution of 2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxylic acid (3.0 g, 15.18 mmol) in methanol (5 mL), sodium methoxide solution (30% in methanol) (14.09 mL, 76 mmol) was added at 25°C. The resulting reaction mixture was stirred at 80°C for 24 hours. After completion of the reaction, the reaction solution was evaporated under reduced pressure, diluted with water (10 mL), and the aqueous layer was adjusted to pH 3 with concentrated hydrochloric acid to obtain a precipitate. The precipitated aqueous layer was extracted with ethyl acetate (3 x 200 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography to obtain 2-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxylic acid (2.45 g, 12.68 mmol, 84% yield). 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.24 (s, 1H), 4.17 (s, 3H), 3.00-2.86 (m, 4H), 2.27-2.11 (m, 2H); ESI MS (m / z) 193.9 (MH) + .

[0249] Example 6: Preparation of 2-methoxy-5,6,7,8-tetrahydroquinoline-3-carboxylic acid a) Step 1: Preparation of sodium (E)-(2-oxocyclohexylidene)methanolate To a stirred suspension of sodium ethoxide (27.0 g, 397 mmol) in diethyl ether (200 mL) was added cyclohexanone (31.6 mL, 306 mmol) and ethyl formate (24.59 mL, 306 mmol) under nitrogen at 0 °C. The resulting reaction mixture was stirred for 24 h at 10–15 °C. After completion of the reaction, the precipitated product was filtered, washed with hexane (2 × 20 mL), and dried under reduced pressure to give sodium (E)-(2-oxocyclohexylidene) methanolate (32.84 g, 222 mmol, 73% yield). 1 H-NMR (400 MHz, D2O) δ 8.95 (s, 1H), 8.32 (s, 1H), 2.10-2.03 (m, 4H), 1.60-1.52 (m, 2H), 1.51-1.43 (m, 2H).

[0250] b) Step 2: Preparation of 2-hydroxy-5,6,7,8-tetrahydroquinoline-3-carbonitrile To a stirred solution of sodium (E)-(2-oxocyclohexylidene) methanolate (30 g, 203 mmol) in water (200 mL), 2-cyanoacetamide (17.88 g, 213 mmol) and piperidine acetate (30 mL) (prepared using acetic acid 6.81 mL, water 11.52 mL, and piperidine 11.77 mL) were added at 25° C. The resulting reaction mixture was stirred at 100° C. for 12 hours. After completion of the reaction, the reaction mixture was cooled to 25° C., acetic acid (20 mL) was added, and the mixture was further stirred at 25° C. for 1 hour. The resulting reaction mixture was cooled to 0° C. to obtain a precipitate. The resulting precipitate was filtered, washed with water, and dried to obtain 2-hydroxy-5,6,7,8-tetrahydroquinoline-3-carbonitrile (21.49 g, 123 mmol, 61% yield). 1 H-NMR (400 MHz, DMSO-d6) δ 7.87 (s, 1H), 2.54 (t, J = 5.9 Hz, 3H), 2.41 (t, J = 5.9 Hz, 2H), 1.77-1.61 (m, 4H); ESI MS (m / z) 174.95 (MH) + .

[0251] c) Step 3: Preparation of 2-hydroxy-5,6,7,8-tetrahydroquinoline-3-carboxylic acid A suspension of 2-hydroxy-5,6,7,8-tetrahydroquinoline-3-carbonitrile (10 g, 57.4 mmol) in concentrated hydrochloric acid (60 mL, 37%) was stirred at 100-110° C. for 12 hours. After completion of the reaction, the reaction mixture was evaporated under reduced pressure and dried to give 2-hydroxy-5,6,7,8-tetrahydroquinoline-3-carboxylic acid (10.05 g, 52.0 mmol, 91% yield). 1 H-NMR (400 MHz, DMSO-d6) δ 14.91 (s, 1H), 13.05 (s, 1H), 8.11 (s, 1H), 2.65 (t, J = 6.0 Hz, 2H), 2.55 (t, J = 5.9 Hz, 2H), 1.75-1.64 (m, 4H); ESI MS (m / z) 193.90 (MH) + .

[0252] d) Step 4: Preparation of 2-chloro-5,6,7,8-tetrahydroquinoline-3-carboxylic acid To a stirred solution of phosphorus oxychloride (28.9 mL, 311 mmol) was added 2-hydroxy-5,6,7,8-tetrahydroquinoline-3-carboxylic acid (3.0 g, 15.53 mmol) at 25° C. The resulting reaction mixture was stirred at 110° C. for 5 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure and diluted with water (50 mL). The aqueous layer was extracted with ethyl acetate (3×200 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated to give 2-chloro-5,6,7,8-tetrahydroquinoline-3-carboxylic acid (1.97 g, 9.30 mmol, 60% yield). 1 H-NMR (400 MHz, CHLOROFORM-D) δ 8.02 (s, 1H), 2.95 (t, J = 6.4 Hz, 2H), 2.79 (t, J = 6.3 Hz, 2H), 1.94-1.80 (m, 4H); ESI MS (m / z) 211.85 (MH) + .

[0253] e) Step 5: Preparation of 2-methoxy-5,6,7,8-tetrahydroquinoline-3-carboxylic acid To a stirred solution of 2-chloro-5,6,7,8-tetrahydroquinoline-3-carboxylic acid (1.0 g, 4.72 mmol) in methanol (5 mL) was added sodium methoxide solution (30% in methanol) (8.77 mL, 47.2 mmol) at 25 °C. The resulting reaction mixture was stirred at 60 °C for 48 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure, diluted with water (10 mL), and the aqueous layer was acidified with 1 N HCl (10 mL) and extracted with ethyl acetate (2 x 150 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 2-methoxy-5,6,7,8-tetrahydroquinoline-3-carboxylic acid (740 mg, 3.6 mmol, 74% yield). 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.11 (s, 1H), 4.13 (s, 3H), 2.86-2.72 (m, 4H), 1.88-1.80 (m, 4H); ESI MS (m / z) 207.95 (MH) + .

[0254] Example 7: Preparation of 2,4-dimethyl-1-phenylpentan-2-amine a) Step 1: Preparation of 2,4-dimethyl-1-phenylpentan-2-ol To a stirred solution of 4-methylpentan-2-one (5 g, 49.9 mmol) in tetrahydrofuran (40 mL), benzylmagnesium chloride (37.4 mL, 74.9 mmol) was added dropwise at 0° C., and the resulting reaction mixture was warmed to 25° C. and stirred at 25° C. for 3 h. After completion of the reaction, the reaction mixture was quenched with 2 N hydrochloric acid (50 mL) and extracted with ethyl acetate (3×100 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography to give 2,4-dimethyl-1-phenylpentan-2-ol (4 g, 42% yield). 1 H-NMR (400 MHz, CDCl3) δ 7.29-7.33 (m, 2H), 7.27 (d, J = 1.5 Hz, 1H), 7.20-7.25 (m, 3H), 2.80 (d, J = 13.4 Hz, 1H), 2.71 (d, J = 13.1 Hz, 1H), 1.85-1.95 (m, 1H), 1.36-1.48 (m, 2H), 1.16 (s, 3H), 0.90-1.00 (m, 6H).

[0255] b) Step 2: Preparation of 2-chloro-N-(2,4-dimethyl-1-phenylpentan-2-yl)acetamide To a stirred solution of 2-chloroacetonitrile (0.99 mL, 15.60 mmol) and 2,4-dimethyl-1-phenylpentan-2-ol (2 g, 10.40 mmol) in acetic acid (6 mL), sulfuric acid (2.0 ml, 37.5 mmol) was added dropwise at 0° C. The resulting reaction mixture was stirred at 25° C. for 16 h. After completion of the reaction, the reaction mixture was neutralized with saturated sodium bicarbonate solution (20 mL) and extracted with ethyl acetate (3×20 mL). The organic layer was washed with brine (20 mL), dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography to give 2-chloro-N-(2,4-dimethyl-1-phenylpentan-2-yl)acetamide (1.7 g, 6.35 mmol, 61% yield). ESI MS (m / z) 267.80 (MH) + .

[0256] c) Step 3: Preparation of 2,4-dimethyl-1-phenylpentan-2-amine To a stirred solution of 2-chloro-N-(2,4-dimethyl-1-phenylpentan-2-yl)acetamide (1.7 g, 6.35 mmol) and thiourea (0.58 g, 7.62 mmol) in ethanol (20 mL) was added acetic acid (3 mL, 52.4 mmol) at 25 °C. The resulting reaction mixture was stirred at 80 °C for 36 h. After completion of the reaction, the reaction mixture was diluted with 1 N hydrochloric acid (20 mL) and extracted with ethyl acetate (2 x 20 mL). The aqueous layer was neutralized with 2 N sodium hydroxide and extracted with hexane (2 x 100 mL). The combined organic layers were concentrated under reduced pressure to give 2,4-dimethyl-1-phenylpentan-2-amine (0.7 g, 3.66 mmol, 58% yield). ESI MS (m / z) 191.80 (MH) + .

[0257] Example 8: Preparation of 3-amino-3-methyl-1-phenylbutan-2-ol a) Step 1: Preparation of tert-butyl (1-hydroxy-2-methylpropan-2-yl)carbamate To a solution of 2-amino-2-methylpropan-1-ol (4 g, 44.9 mmol) in dichloromethane (50 mL), di-tert-butyl dicarbonate (10.42 mL, 44.9 mmol) and triethylamine (6.25 mL, 44.9 mmol) were added at 25° C., and the resulting reaction mixture was stirred for 2.5 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and diluted with 10% aqueous citric acid. The aqueous layer was extracted with ethyl acetate (3×50 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography to give tert-butyl (1-hydroxy-2-methylpropan-2-yl)carbamate (8 g, 42.3 mmol, 94% yield). 1 H-NMR (400 MHz, DMSO-d6) δ 6.09 (s, 1H), 4.68 (t, J = 5.8 Hz, 1H), 3.28 (d, J = 5.8 Hz, 2H), 1.35 (s, 9H), 1.12 (s, 6H).

[0258] b) Step 2: Preparation of tert-butyl (2-methyl-1-oxopropan-2-yl)carbamate To a solution of tert-butyl (1-hydroxy-2-methylpropan-2-yl) carbamate (10 g, 52.8 mmol) in dichloromethane (50 mL) was added Dess-Martin periodinane (28.0 g, 66.0 mmol) at 0° C., and the resulting reaction mixture was stirred at 25° C. for 16 hours. After completion of the reaction, the reaction mixture was filtered, and the filtrate was washed with saturated sodium thiosulfate solution (50 mL) and 10% sodium bicarbonate solution (100 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography to obtain tert-butyl (2-methyl-1-oxopropan-2-yl) carbamate as a white solid (8 g, 42.7 mmol, 81% yield). 1H-NMR (400 MHz, DMSO-d6) δ 9.28 (s, 1H), 7.44 (s, 1H), 1.37 (s, 9H), 1.11 (s, 6H).

[0259] c) Step 3: Preparation of tert-butyl (3-hydroxy-2-methyl-4-phenylbutan-2-yl)carbamate To a stirred solution of tert-butyl (2-methyl-1-oxopropan-2-yl) carbamate (4.2 g, 22.43 mmol) in tetrahydrofuran (30 mL), benzylmagnesium chloride (2 M in tetrahydrofuran, 33.6 mL, 67.3 mmol) was added dropwise at -78°C, and the resulting reaction mixture was stirred at the same temperature for 2 hours. After completion of the reaction, the reaction mixture was quenched with water (50 mL), and the aqueous layer was extracted with ethyl acetate (3×50 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography to give tert-butyl (3-hydroxy-2-methyl-4-phenylbutan-2-yl) carbamate (2.1 g, 7.5 mmol, 34% yield). 1 H-NMR (400 MHz, DMSO-d6) δ 7.28-7.23 (m, 2H), 7.20-7.09 (m, 3H), 6.38 (s, 1H), 4.66 (d, J = 7.1 Hz, 1H), 3.87-3.80 (m, 1H), 2.79 (d, ESI MS (m / z) 280.1 (MH) + .

[0260] d) Step 4: Preparation of 3-amino-3-methyl-1-phenylbutan-2-ol To a stirred solution of t-butyl (3-hydroxy-2-methyl-4-phenylbutan-2-yl) carbamate (2.0 g, 7.16 mmol) in dichloromethane (20 mL) was added trifluoroacetic acid (5.52 mL, 71.6 mmol) dropwise at 0° C., and the resulting reaction mixture was warmed to 25° C. and stirred for 1 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure, neutralized with saturated sodium carbonate solution (10 mL), and the aqueous layer was extracted with dichloromethane (3×25 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography to give 3-amino-3-methyl-1-phenylbutan-2-ol (1.2 g, 6.7 mmol, 94% yield). 1 H-NMR (400 MHz, CHLOROFORM-D) δ 7.33-7.26 (m, 3H), 7.25-7.20 (m, 2H), 3.47 (dd, J = 10.5, 2.4 Hz, 1H), 2.87 (dd, J = 13.7, 2.2 Hz, 1H), 2.53 (dd, J = 13.7, 10.5 Hz, 1H), 1.20 (s, 3H), 1.15 (s, 3H); ESI MS (m / z) 180.1 (MH) + .

[0261] Example 9: Preparation of 2-amino-2-methyl-1-phenylbutan-2-ol a) Step 1: Preparation of tert-butyl (1-hydroxy-2-methyl-1-phenylpropan-2-yl)carbamate To a stirred solution of tert-butyl (2-methyl-1-oxopropan-2-yl)carbamate (3.5 g, 18.7 mmol) in tetrahydrofuran (30 mL), phenylmagnesium bromide (18.7 mL, 2 M tetrahydrofuran solution, 37.4 mmol) was added under inert atmosphere at -78°C, and the resulting reaction mixture was stirred at the same temperature for 2 h. After completion of the reaction, the reaction mixture was quenched with water (50 mL) and the aqueous layer was extracted with ethyl acetate (3×50 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography to give tert-butyl (1-hydroxy-2-methyl-1-phenylpropan-2-yl)carbamate (2.7 g, 10.2 mmol, 54% yield). 1 H-NMR (400 MHz, CHLOROFORM-D) δ 7.32-7.27 (m, 5H), 5.07-5.28 (1H), 4.71 (s, 1H), 4.51 (s, 1H), 1.47 (s, 9H), 1.42 (s, 3H), 1.18 (s, 3H); ESI MS (m / z) 266.05 (MH) + .

[0262] b) Step 2: Preparation of 2-amino-2-methyl-1-phenylpropan-1-ol To a stirred solution of tert-butyl (1-hydroxy-2-methyl-1-phenylpropan-2-yl) carbamate (2.5 g, 9.42 mmol) in dichloromethane (10 mL) was added trifluoroacetic acid (3.63 mL, 47.1 mmol) dropwise at 0° C., and the resulting reaction mixture was warmed to 25° C. and stirred for 1 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure, neutralized with saturated sodium carbonate (20 mL), and the aqueous layer was extracted with dichloromethane (3×25 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography to give 2-amino-2-methyl-1-phenylpropan-1-ol (1.2 g, 7.26 mmol, 77% yield). 1H-NMR (400 MHz, CHLOROFORM-D) δ 7.34-7.28 (m, 5H), 4.50 (s, 1H), 4.12 (q, J = 7.2 Hz, 1H), 1.19 (s, 3H), 1.02 (s, 3H).

[0263] Example 10: Preparation of 2-amino-2-methylpropyl-2-methylbenzoate a) Step 1: Preparation of 2-((tert-butoxycarbonyl)amino)-2-methylpropyl-2-methylbenzoate To a stirred solution of tert-butyl (1-hydroxy-2-methylpropan-2-yl)carbamate (5.2 g, 27.5 mmol) and N,N-diisopropylethylamine (7.20 mL, 41.2 mmol) in dichloromethane (50 mL), 2-methylbenzoyl chloride (4.25 g, 27.5 mmol) was added dropwise at 0 °C, and the resulting mixture was stirred at 25 °C for 3 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure, diluted with water (20 mL), and the aqueous layer was extracted with ethyl acetate (3 × 25 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated to give 2-((tert-butoxycarbonyl)amino)-2-methylpropyl 2-methylbenzoic acid (8 g, 26.0 mmol, 95% yield). 1H-NMR (400 MHz, CHLOROFORM-D) δ 7.91 (dd, J = 8.2, 1.3 Hz, 1H), 7.43-7.39 (m, 1H), 7.35-7.30 (m, 1H), 7.20-7.15 (m, 1H), 4.64 (s, 1H), 4.36 (s, 2H), 2.60 (s, 3H), 1.38 (s, 6H).

[0264] b) Step 2: Preparation of 2-amino-2-methylpropyl 2-methylbenzoic acid To a stirred solution of 2-((tert-butoxycarbonyl)amino)-2-methylpropyl 2-methylbenzoic acid (8 g, 26.0 mmol) in dichloromethane (50 mL) was added trifluoroacetic acid (10.03 mL, 130 mmol) dropwise at 0° C., and the resulting reaction mixture was warmed to 25° C. and stirred for 1 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure, neutralized with saturated sodium carbonate (20 mL), and the aqueous layer was extracted with dichloromethane (3×25 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography to give 2-amino-2-methylpropyl 2-methylbenzoic acid (3.6 g, 17.37 mmol, 67% yield). 1 H-NMR (400 MHz, CHLOROFORM-D) δ 8.00 (dd, J = 7.7, 1.3 Hz, 1H), 7.38 (td, J = 7.5, 1.3 Hz, 1H), 7.24-7.17 (m, 2H), 4.38-5.16 (2H), 4.23 (s, 2H), 2.55 (s, 3H), 1.38 (s, 6H); ESI MS (m / z) 208.10 (MH) + .

[0265] Example 11: Preparation of 1-((2-fluorobenzyl)oxy)-2-methylpropan-2-amine A suspension of sodium hydride (1.346 g, 33.7 mmol, 60% dispersion in mineral oil) in tetrahydrofuran (10 mL) was stirred with a solution of 2-amino-2-methylpropan-1-ol (1 g, 11.2 mmol) in tetrahydrofuran (5 mL) at 25 °C under nitrogen for 1 h. To this reaction mixture, 1-(bromomethyl)-2-fluorobenzene (1.767 mL, 14.58 mmol) was added at 0 °C and the resulting reaction mixture was stirred for an additional 2 h. After completion of the reaction, the reaction mixture was quenched with saturated ammonium chloride solution (50 mL) and the aqueous layer was extracted with ethyl acetate (3 × 50 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated and purified by column chromatography to give 1-((2-fluorobenzyl)oxy)-2-methylpropan-2-amine (0.67 g, 3.40 mmol, 30% yield). 1H-NMR (400 MHz, CHLOROFORM-D) δ 7.41 (td, J = 7.5, 1.7 Hz, 1H), 7.26-7.22 (m, 1H), 7.11 (td, J = 7.5, 1.1 Hz, 1H), 7.04-6.99 (m, 1H), 4.59 (s, 2H), 3.22 (s, 2H), 1.09 (s, 6H); ESI MS (m / z) 197.95 (MH) + .

[0266] Example 12: Preparation of 2-methyl-1-(pyridin-2-yloxy)propan-2-amine A suspension of sodium hydride (0.897 g, 22.4 mmol, 60% dispersion in mineral oil) in tetrahydrofuran (10 mL) was stirred at 25° C. for 1 h with a solution of 2-amino-2-methylpropan-1-ol (1 g, 11.22 mmol) in tetrahydrofuran (10 mL) under nitrogen atmosphere. To this reaction mixture, 2-fluoropyridine (1.307 g, 13.46 mmol) was added at 0° C., and the resulting reaction mixture was stirred for an additional 3 h. After completion of the reaction, the reaction mixture was quenched with saturated ammonium chloride solution (50 mL) and the aqueous layer was extracted with ethyl acetate (3×50 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography to give 2-methyl-1-(pyridin-2-yloxy)propan-2-amine (1.552 g, 9.3 mmol, 83% yield). 1 H-NMR (400 MHz, CHLOROFORM-D) δ 8.13 (dq, J = 5.0, 1.0 Hz, 1H), 7.57 (ddd, J = 8.7, 6.7, 1.6 Hz, 1H), 6.86 (ddd, J = 7.1, 5.1, 1.0 Hz, 1H), 6.77 (dt, J = 8.4, 0.9 Hz, 1H), 4.05 (s, 2H), 1.28-1.18 (m, 7H); ESI MS (m / z) =167.1 (MH) + .

[0267] Example 13: Preparation of 1-amino-1-(4-fluorophenyl)-2-methylpropan-2-ol To a stirred solution of methyl 2-amino-2-(4-fluorophenyl)acetate (5.0 g, 27.3 mmol) in tetrahydrofuran (50 mL), methylmagnesium bromide (78 mL, 1.4 M in tetrahydrofuran, 39 mL, 109 mmol) was added under inert atmosphere at -78°C, and the resulting reaction mixture was stirred at the same temperature for 2 hours. After completion of the reaction, the reaction mixture was quenched with water (50 mL), and the aqueous layer was extracted with ethyl acetate (3 x 50 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography to give 1-amino-1-(4-fluorophenyl)-2-methylpropan-2-ol (4.0 g, 27.0 mmol, 80% yield). ESI MS (m / z) =184.0 (MH). + .

[0268] Example 14: Preparation of N-(1-(2-fluorophenyl)propan-2-yl)-O-methylhydroxylamine a) Step 1: Preparation of 1-(2-fluorophenyl)propan-2-one O-methyloxime To a stirred solution of 1-(2-fluorophenyl)propan-2-one (5 g, 32.9 mmol) in ethanol (20 mL), O-methylhydroxylamine hydrochloride (4.12 g, 49.3 mmol) and sodium acetate (4.04 g, 49.3 mmol) were added at 25° C., and the resulting reaction mixture was stirred for 2 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure to give 1-(2-fluorophenyl)propan-2-one O-methyloxime. 1H-NMR (400 MHz, CHLOROFORM-D) δ 7.23-7.16 (m, 2H), 7.09-7.00 (m, 2H), 3.87 (s, 3H), 3.52 (s, 2H), 1.76 (s, 3H); ESI MS (m / z) =181.95 (MH). + .

[0269] b) Step 2: Preparation of N-(1-(2-fluorophenyl)propan-2-yl)-O-methylhydroxylamine To a stirred solution of 1-(2-fluorophenyl)propan-2-one O-methyloxime (1 g, 5.52 mmol) in acetic acid (5 mL), sodium cyanoborohydride (0.694 g, 11.04 mmol) was added slowly at 20° C., and the resulting reaction mixture was stirred for 30 min. After completion of the reaction, the reaction mixture was quenched with water (30 mL) and a saturated solution of sodium bicarbonate, and the aqueous layer was extracted with ethyl acetate (3×50 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated, and purified by column chromatography to give N-(1-(2-fluorophenyl)propan-2-yl)-O-methylhydroxylamine (0.8 g, 4.37 mmol, 79% yield). 1 H-NMR (400 MHz, CHLOROFORM-D) δ 7.22-7.13 (m, 2H), 7.08-6.99 (m, 2H), 4.50 (s, 1H), 3.56 (s, 3H), 3.33-3.24 (m, 1H), 2.92-2.87 (m, 1H), 2.65 (qd, J = 6.8, 1.1 Hz, 1H), 1.07 (dd, J = 6.5, 0.6 Hz, 3H); ESI MS (m / z) =184.0 (MH) + .

[0270] Example 15: Preparation of 1-(4-fluorophenoxy)-2,4-dimethylpent-4-en-2-amine a) Step 1: Preparation of 1-(4-fluorophenoxy)propan-2-one To a stirred solution of 4-fluorophenol (10 g, 89 mmol) in acetone (150 ml) was added potassium carbonate (14.79 g, 107 mmol), potassium iodide (1.481 g, 8.92 mmol) and 1-chloropropan-2-one (8.54 mL, 107 mmol) under inert atmosphere at 25° C. The resulting reaction mixture was stirred at 50° C. for 6 h. After completion of the reaction, the reaction mixture was quenched with water (50 mL) and the aqueous layer was extracted with ethyl acetate (3×100 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated to give 1-(4-fluorophenoxy)propan-2-one (15 g, 89 mmol, 100% yield). 1 H-NMR (400 MHz, CHLOROFORM-D) δ 7.01-6.95 (m, 2H), 6.86-6.81 (m, 2H), 4.51 (s, 2H), 2.27 (s, 3H).

[0271] b) Step 2: Preparation of N-(1-(4-fluorophenoxy)propan-2-ylidene)-2-methylpropane-2-sulfinamide To a stirred solution of 1-(4-fluorophenoxy)propan-2-one (10 g, 59.5 mmol) in tetrahydrofuran (100 mL), titanium(IV) isopropoxide (22.65 mL, 77 mmol) and 2-methylpropane-2-sulfinamide (8.65 g, 71.4 mmol) were added under inert atmosphere at 25° C. The resulting reaction mixture was stirred at 60° C. for 6 h. After completion of the reaction, the reaction mixture was quenched with saturated sodium bicarbonate solution (100 mL) and the aqueous layer was extracted with ethyl acetate (3×100 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated and purified by column chromatography to give N-(1-(4-fluorophenoxy)propan-2-ylidene)-2-methylpropane-2-sulfinamide (5.6 g, 20.6 mmol, 48% yield). 1H-NMR (400 MHz, CHLOROFORM-D) δ 7.01-6.94 (m, 3H), 6.88-6.81 (m, 3H), 4.61 (d, J = 1.7 Hz, 2H), 2.40 (s, 3H), 1.21 (d, J = 17.4 Hz, 10H)); ESI MS (m / z) =272.05 (MH) + .

[0272] c) Step 3: Preparation of N-(-1-(4-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-2-methylpropane-2-sulfinamide To a stirred suspension of magnesium (0.448 g, 18.43 mmol) and iodine (100 mg) in tetrahydrofuran (20 mL), 3-chloro-2-methylprop-1-ene (1.092 mL, 11.1 mmol) was added at 65° C. and stirred for 1 h. The reaction mixture was cooled to −78° C. and a solution of N-(1-(4-fluorophenoxy)propan-2-ylidene)-2-methylpropane-2-sulfinamide (2.5 g, 9.21 mmol) in tetrahydrofuran (5 mL) was added under inert atmosphere. The resulting reaction mixture was further stirred at 25° C. for 8 h. After completion of the reaction, the reaction mixture was quenched with saturated ammonium chloride (20 mL) and the aqueous layer was extracted with ethyl acetate (3×25 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated and purified by column chromatography to give N-1-(4-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-2-methylpropane-2-sulfinamide (1 g, 3.1 mmol, 40% yield). ESI MS (m / z) =328.05 (MH). + .

[0273] d) Step 4: Preparation of 1-(4-fluorophenoxy)-2,4-dimethylpent-4-en-2-amine To a stirred solution of N-(-1-(4-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-2-methylpropane-2-sulfinamide (500 mg, 1.527 mmol) in methanol (10 mL), hydrochloric acid (15 mmol, 2.5 mL, 4 N in dioxane) was added at 0° C., and the resulting reaction mixture was stirred for 4 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure to give 1-(4-fluorophenoxy)-2,4-dimethylpent-4-en-2-amine (341 mg, 1.53 mmol, 100% yield). ESI MS (m / z) =224.05 (MH). + .

[0274] Example 16: Preparation of 1-(4-fluorophenyl)-2,4-dimethylpent-4-en-2-amine a) Step 1: Preparation of N-(1-(4-fluorophenyl)propan-2-ylidene)-2-methylpropane-2-sulfinamide To a stirred solution of 1-(4-fluorophenoxy)propan-2-one (10 g, 59.5 mmol) in tetrahydrofuran (100 mL), titanium(IV) isopropoxide (22.65 mL, 77 mmol) and 2-methylpropane-2-sulfinamide (8.65 g, 71.4 mmol) were added under inert atmosphere at 25° C. The resulting reaction mixture was stirred at 60° C. for 6 h. After completion of the reaction, the reaction mixture was quenched with saturated sodium bicarbonate solution (100 mL) and the aqueous layer was extracted with ethyl acetate (3×100 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated and purified by column chromatography to give N-(1-(4-fluorophenyl)propan-2-ylidene)-2-methylpropane-2-sulfinamide (13.4 g, 52.5 mmol, 80% yield).

[0275] b) Step 2: Preparation of N-(1-(4-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)-2-methylpropane-2-sulfinamide To a stirred suspension of magnesium (3.71 g, 153 mmol) and iodine (100 mg) in tetrahydrofuran (150 mL), 3-chloro-2-methylprop-1-ene (15.08 mL, 153 mmol) was added at 65° C., and the resulting reaction mixture was stirred for 1 h. The reaction mixture was cooled to −78° C., and a solution of N-(1-(4-fluorophenyl)propan-2-ylidene)-2-methylpropane-2-sulfinamide (13 g, 50.9 mmol) in tetrahydrofuran (20 mL) was added under inert atmosphere. The resulting reaction mixture was further stirred at 25° C. for 8 h. After completion of the reaction, the reaction mixture was quenched with saturated ammonium chloride (20 mL) and the aqueous layer was extracted with ethyl acetate (3×25 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated and purified by column chromatography to give N-(1-(4-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)-2-methylpropane-2-sulfinamide (8 g, 25.7 mmol, 50% yield). ESI MS (m / z) =311.6 (MH). + .

[0276] c) Step 3: Preparation of 1-(4-fluorophenyl)-2,4-dimethylpent-4-en-2-amine To a stirred solution of N-(1-(4-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)-2-methylpropane-2-sulfinamide (10 g, 32.1 mmol) in methanol (30 mL) was added hydrochloric acid (321 mmol, 80 mL, 4 N dioxane solution) at 0° C., and the resulting reaction mixture was stirred for 4 hours. After completion of the reaction, the reaction mixture was evaporated under reduced pressure to give 1-(4-fluorophenyl)-2,4-dimethylpent-4-en-2-amine (6.5 g, 31.4 mmol, 98% yield). ESI MS (m / z) = 207.65 (MH). + .

[0277] Example 17: Preparation of 1-methyl-N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (Compound No. 1) To a stirred solution of 1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (200 mg, 1.27 mmol) and 2-methyl-1-phenylpropan-2-ol (382 mg, 2.54 mmol) in acetic acid (6 mL), sulfuric acid (0.8 mL) was added dropwise at 0° C., and the resulting reaction mixture was stirred at 25° C. for 8 h. After completion of the reaction, the reaction mixture was neutralized with saturated sodium bicarbonate solution (50 mL) and extracted with ethyl acetate (3×25 mL). The organic layer was washed with brine (20 mL), dried over anhydrous sodium sulfate, concentrated, and purified using reverse phase HPLC to give 1-methyl-N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (250 mg, 0.813 mmol, 64% yield). 1 H-NMR (400 MHz, DMSO-d6) δ 8.66 (d, J = 2.1 Hz, 1H), 8.33 (d, J = 2.1 Hz, 1H), 7.62 (s, 1H), 7.58 (d, J = 3.4 Hz, 1H), 7.24-7.20 (m, 2H), 7.18-7.12 (m, 3H), 6.54 (d, J = 3.4 Hz, 1H), 3.83 (s, 3H), 3.14 (s, 2H), 1.35 (s, 6H); ESI MS (m / z) 308 (MH) + .

[0278] Example 18: Preparation of N-(1-(4-fluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (Compound No. 74) To a stirred solution of 1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (329 mg, 1.87 mmol) in dichloromethane (10 mL) was added hydroxybenzotriazole (286 mg, 1.87 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (358 mg, 1.87 mmol). After 10 minutes, triethylamine (0.87 mL, 6.23 mmol) and 1-(4-fluorophenyl)-2-methylpropan-2-amine (250 mg, 1.45 mmol) were added to the reaction mixture under inert atmosphere at 25° C., and the resulting reaction mixture was stirred at 25° C. for 16 hours. After completion of the reaction, dichloromethane was evaporated and the reaction mixture was quenched with water (10 mL). The reaction mixture was extracted with ethyl acetate (2×20 mL) and washed with brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and evaporated to give the crude product, which was purified by column chromatography using an appropriate eluent to give the pure product N-(1-(4-fluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (120 mg, 0.37 mmol, 30% yield). 1 H-NMR (400 MHz, CHLOROFORM-D) δ 8.58 (d, J = 2.0 Hz, 1H), 8.16 (d, J = 2.0 Hz, 1H), 7.28-7.20 (m, 5H), 6.49 (d, J = 3.7 Hz, 1H), 3.90 (s, 3H), 3.76 (q, J = 7.3 Hz, 1H), 1.58 (s, 3H), 1.39-1.36 (m, 6H); ESI MS (m / z) 326.05 (MH) + .

[0279] The following compounds in Table 1 were prepared using procedures similar to those described in Examples 17 and 18 above.

[0280] [Table 1-1] [Table 1-2]

Table 1-3

Table 1-4

Table 1-5

Table 1-6

Table 1-7

Table 1-8

Table 1-9

Table 1-10

Table 1-11

Table 1-12

Table 1-13

Table 1-14

Table 1-15

Table 1-16

Table 1-17

Table 1-18

Table 1-19

Table 1-20

Table 1-21

Table 1-22

Table 1-23

Table 1-24

Table 1-25

Table 1-26

Table 1-27

Table 1-28

Table 1-29

Table 1-30

Table 1-31

Table 1-32

Table 1-33

Table 1-34

Table 1-35

Table 1-36

[0281] Biological Examples: As described herein, the compounds of general formula (I) exhibit fungicidal activity against a number of plant pathogens that attack important agricultural crops. The compounds of the present invention were evaluated for their activity as described in the following tests.

[0282] Example 1: Pyricularia oryzae (Rice blast): Compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar media immediately prior to dispensing into Petri plates. 5 mL media containing the desired test concentrations of compounds was dispensed into 60 mm sterile Petri plates. After solidification, each plate was inoculated with a 5 mm sized mycelial disk taken from the periphery of an actively growing pathogenic culture plate. Plates were incubated in a growth chamber at 25°C and 60% relative humidity for 7 days, and radial growth was measured and compared to that of an untreated control. Compounds 1, 2, 3, 7, 8, 11, 12, 13, 20, 21, 23, 24, 25, 29, 30, 34, 36, 38, 39, 40, 42, 43, 44, 45, 46, 47, 48, 50, 51, 53, 56, 58, 59, 63, 64, 65, 69, 71, 79, 81, 83, 85, 98, 99, 100, 108, 109, 119, 124, 131, 133, 141, 143, 161, 176, 180, 185, 189, 214, 219, 220, 239, and 254, at 300 ppm, gave more than 70% control in these tests compared to untreated checks which showed significant growth of the pathogen.

[0283] Example 2: Botrytis cinerea (gray mold): Compounds were dissolved in 0.3% dimethyl sulfoxide and added to potato dextrose agar media immediately before dispensing into Petri plates. 5 mL medium containing the desired concentration of compound was dispensed into 60 mm sterile Petri plates. After solidification, each plate was inoculated with a 5 mm sized mycelial disk taken from the periphery of an actively growing pathogenic culture plate. Plates were incubated in a growth chamber at 22°C and 90% relative humidity for 7 days, and radial growth was measured and compared to that of an untreated control. Compounds 40 50 55 63 67 72 73 75 78 82 89 98 100 101 105 106 109 118 144 148 149 159 160 187 189 190 194 252 254 at 300 ppm gave more than 70% control in these tests compared to untreated checks which showed significant growth of the pathogen.

[0284] Example 3: Alternaria solani (Early blight of tomato / potato): Compounds were dissolved in 0.3% dimethyl sulfoxide and added to potato dextrose agar medium immediately prior to dispensing into Petri plates. 5 mL medium containing the desired concentration of compound was dispensed into 60 mm sterile Petri plates. After solidification, each plate was inoculated with a 5 mm sized mycelial disk taken from the periphery of an actively growing pathogen culture plate. Plates were incubated in a growth chamber at 25°C and 60% relative humidity for 7 days and radial growth was measured and compared to that of an untreated control. Compounds 1 2 5 6 7 10 11 12 13 14 28 47 50 85 99 109 129 144 at 300 ppm gave more than 70% control in these tests compared to untreated checks which showed significant growth of the pathogen.

[0285] Example 4: Colletotrichum capsici (Anthracnose): Compounds were dissolved in 0.3% dimethyl sulfoxide and added to potato dextrose agar media immediately before dispensing into Petri plates. 5 mL medium containing the desired concentration of compounds was dispensed into 60 mm sterile Petri plates. After solidification, each plate was inoculated with a 5 mm sized mycelial disk taken from the periphery of an actively growing pathogenic culture plate. Plates were incubated in a growth chamber at 25°C and 60% relative humidity for 7 days, and radial growth was measured and compared to that of an untreated control. Compounds 1, 2, 3, 6, 8, 10, 11, 12, 13, 20, 21, 23, 25, 28, 29, 34, 36, 39, 44, 45, 50, 62, 73, 75, 80, 81, 90, 99, 101, 102, 103, 116, 121, 122, 127, 129, 144, 155, 160, 175, 181, 187, 190, 211, 230, 247, and 252, at 300 ppm, gave more than 70% control in these tests compared to untreated checks which showed significant growth of the pathogen.

[0286] Example 5: Corynespora cassiicola (tomato spot disease): Compounds were dissolved in 0.3% dimethyl sulfoxide and added to potato dextrose agar media immediately prior to dispensing into Petri dishes. 5 mL medium containing the desired concentration of compound was dispensed into 60 mm sterile Petri dishes. After solidification, each plate was inoculated with a 5 mm sized mycelial disk taken from the periphery of an actively growing pathogen culture plate. Plates were incubated in a growth chamber at 25°C and 70% relative humidity for 7 days and radial growth was measured and compared to that of an untreated control. Compounds 2, 6, 43, 107, 109, 121, 125, 127 and 129 at 300 ppm gave more than 70% control in these tests compared to untreated checks which showed significant growth of the pathogen.

[0287] Example 6: Fusarium culmorum (root rot / head blight of cereals): Compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar media immediately prior to dispensing into Petri plates. 5 mL media containing the desired concentrations of compounds were dispensed into 60 mm sterile Petri plates. After solidification, each plate was inoculated with a 5 mm sized mycelial disk taken from the periphery of an actively growing pathogen culture plate. Plates were incubated in a growth chamber at 25°C and 60% relative humidity for 7 days and radial growth was measured. Compounds 2 and 13 at 300 ppm gave more than 70% control in these tests compared to untreated checks which showed significant growth of the pathogen.

[0288] Example 7: Phytophthora infestans (late blight of potato and tomato) Compounds were dissolved in 0.3% DMSO and added to the rye agar medium immediately before dispensing into the Petri dishes. 5 mL of medium containing the desired concentration of compounds was dispensed into 60 mm sterile Petri dishes. After solidification, each plate was inoculated with a 5 mm sized mycelial disk taken from the periphery of an actively growing pathogenic culture plate. The plates were incubated in a growth chamber at 18 °C and 95% relative humidity for 7 days and radial growth was measured. Compounds 10, 13, 27, 28, 30, 39, 41, 73, 79, 86, 91, 92, 95, 98, 105, 109, 111, 114, 119, 123, 144, 146, 156, 175, 196, 201, 202, 207, 212, 215, 216, 223, 229, 230, 233, 246, 248, 249, 250, and 252, at 300 ppm, gave more than 70% control compared to untreated checks, which showed widespread disease incidence in these tests.

[0289] Example 8: Parastagonospora nodorum (PARANO) PARANO (10 5Potato dextrose (PDB) liquid medium (Difco) containing spore suspension (100 spores / ml) was prepared. For inhibition assays, each test compound was dissolved in dimethyl sulfoxide. 100 μl of test compound in medium solution was added to a 96-well microtiter plate, then an equal volume (100 μl) of spore suspension was added to the well to provide the final test concentration, and the plate was incubated at 18°C ​​for 5-6 days. Growth inhibition was evaluated at OD 600. The inhibition rate was calculated by the following formula: I=(CB)-(TB) / (CB)*100 Where T=treatment, C=control, B=blank Compound 5 6 7 8 10 11 13 16 17 18 23 25 26 27 28 34 36 40 42 43 44 45 47 48 50 56 60 63 67 73 75 78 79 80 81 82 85 86 90 95 99 100 101 102 103 105 106 108 109 118 119 124 135 144 149 150 151 153 155 159 160 173 175 176 179 181 187 190 200 205 210 211 217 223 227 230 232 239 243 244 245 247 249 252 253 254 At 300 ppm, more than 70% control was obtained in these tests compared to untreated checks which showed significant growth of the pathogen.

[0290] Example 9: Venturia inequalis (VENTIN) VENTIN (10 5 Potato dextrose (PDB) liquid medium containing spore suspension (100 spores / ml) was prepared. For inhibition assays, each test compound was dissolved in dimethyl sulfoxide. 100 μl of test compound in medium solution was added to a 96-well microtiter plate, then an equal volume (100 μl) of spore suspension was added to the well to make the final test concentration, and the treated plates were incubated at 18°C ​​for 15–18 days. Growth inhibition was assessed by measuring OD 600. Percent inhibition was calculated by the following formula: I=(CB)-(TB) / (CB)*100 Here, T=treatment group, C=control group, and B=blank. Compounds 39, 41, 44, 47, 49, 52, 53, 62, 63, 64, 67, 68, 69, 73, 75, 79, 80, 81, 83, 102, 107, 127, 132, 144, 146, 155, 160, 161, and 167, at 300 ppm, gave more than 70% control in these tests compared to untreated checks which showed significant growth of the pathogen.

[0291] Example 10: Botrytis cinerea Liquid (BOTRCI): BOTRCI(10 4 Yeast bacterial peptone and sodium acetate (YBA) liquid medium containing 100 spores / ml of spore suspension was prepared. For inhibition assays, each test compound was dissolved in dimethyl sulfoxide. 100 μl of test compound in medium solution was added to a 96-well microtiter plate, then an equal volume (100 μl) of spore suspension was added to the well to make the final test concentration, and the plates were incubated at 22 °C for 5-6 days. Growth inhibition was assessed by measuring the OD at 405 nm. The percent inhibition was calculated by the following formula: I= (CB)-(TB) / (CB) *100 where T is treatment, C is control, and B is blank. Compounds 6, 8, 13, 14, 20, 50, 55, 63, 67, 72, 73, 75, 78, 82, 89, 98, 100, 101, 105, 106, 109, 118, 144, 148, 149, 187, 189, 190, 194, 202, 219, 221, 223, 230, 232, 239, 242, 244, 247, 252, and 254 at 300 ppm gave more than 70% control in these tests compared to untreated checks which showed significant growth of the pathogen.

[0292] Examples of biological tests on plants Compounds were further selected for greenhouse testing. The methods performed to confirm the efficacy of the compounds against each pathogen are as follows:

[0293] Example A: Pyricularia oryzae test on rice Each compound was dissolved in 2% dimethylsulfoxide / acetone and then mixed with water containing an emulsifier to a calibrated spray volume of 30 mL. The spray solution was poured into a spray bottle and further sprayed.

[0294] To test the preventive activity of the compounds, healthy young rice seedlings / plants grown in a greenhouse were sprayed with the active compound formulations at the prescribed application rates in a spray cabinet using a hollow cone nozzle. One day after treatment, 1.4x10 6 The plants were inoculated with a spore suspension containing the Pyricularia oryzae inoculum of 1000 mg / kg / day. The inoculated plants were then placed in a greenhouse at 24°C and 95% relative humidity to observe disease expression.

[0295] Compound performance was assessed visually by rating disease severity (on a 0-100% scale) on treated plants 3, 7, 10, and 15 days after application. Compound efficacy (% control) was calculated by comparing disease ratings of treated plants to untreated controls. Treated plants were also assessed for plant damage by recording symptoms such as necrosis, chlorosis, and stunting. Compounds 26, 116, 119, and 137, at 500 ppm, gave more than 70% control in these trials compared to untreated checks, which showed widespread disease development.

[0296] Example B: Fusarium culmorum test on wheat Each compound was dissolved in 2% dimethylsulfoxide / acetone and then mixed with water containing an emulsifier to a calibrated spray volume of 30 mL. Each spray solution was poured into a spray bottle and sprayed.

[0297] To test the preventive activity of the compounds, healthy young wheat plants grown in a greenhouse were sprayed with the active compound formulations at the defined application rates in a spray cabinet using a hollow cone nozzle. One day after treatment, the plants were sprayed with 2 × 10 6 The plants were then inoculated with a spore suspension containing Fusarium culmorum inoculum of 1000 μg / kg. The inoculated plants were then placed in a greenhouse chamber at 24°C and 80–90% relative humidity to examine disease expression.

[0298] Compound performance was assessed visually by rating disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Compound efficacy (% control) was calculated by comparing disease ratings of treated plants to untreated controls. Treated plants were also assessed for plant damage by recording symptoms such as necrosis, chlorosis and stunting. Compounds 44, 50, 62, 63, 64, 67, 81, 92, 99, 101, 102, 103, 121, 143 and 155, at 500 ppm, gave more than 70% control in these trials compared to untreated checks which showed widespread disease development.

[0299] Example C: Botrytis cinerea test on tomatoes Each compound was dissolved in 2% dimethylsulfoxide / acetone and then mixed with water containing an emulsifier to a calibrated spray volume of 30 mL. Each spray solution was poured into a spray bottle and sprayed.

[0300] To test the preventive activity of the compounds, healthy young bean / chili plants grown in a greenhouse were sprayed with the active compound formulations at the prescribed application rates in a spray cabinet using a hollow cone nozzle. One day after treatment, the plants were sprayed with 1.2 × 10 6 The plants were then inoculated with a spore suspension containing the Botrytis cinerea inoculum. The inoculated plants were then placed in a greenhouse chamber at temperatures between 18 and 20°C and relative humidity between 90 and 100% and examined for disease expression.

[0301] Compound performance was assessed visually by rating disease severity (0-100% scale) on treated plants 3, 7, 10, and 15 days after application. Compound efficacy (% control) was calculated by comparing disease ratings of treated plants and untreated controls. Treated plants were also assessed for plant damage by recording symptoms such as necrosis, chlorosis, and stunting. Compounds 1, 2, 19, 30, 35, 38, 41, 44, 46, 54, 55, 57, 61, 62, 63, 66, 67, 73, 74, 75, 76, 81, 83, 84, 86, 92, 95, 96, 97, 98, 100, 102, 106, 113, 120, 122, 124, 125, 128, 144, 150, 151, and 153, at 500 ppm, gave more than 70% control in these trials compared to untreated checks which showed widespread disease development.

[0302] Example D: Alternaria solani test on tomatoes Each compound was dissolved in 2% dimethylsulfoxide / acetone and then mixed with water containing an emulsifier to a calibrated spray volume of 30 mL. Each spray solution was poured into a spray bottle and sprayed.

[0303] To test the preventive activity of the compounds, healthy young tomato plants grown in a greenhouse were sprayed with the active compound formulations at the prescribed application rates in a spray cabinet using a hollow cone nozzle. One day after treatment, the plants were sprayed with 0.24 × 10 6 The plants were then inoculated with a spore suspension containing the Alternaria solani inoculum of 1000 μg / kg. The inoculated plants were then placed in a greenhouse chamber at a temperature of 22–24°C and a relative humidity of 90–95% and examined for disease expression.

[0304] Compound performance was assessed visually by rating disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Compound efficacy (% control) was calculated by comparing disease ratings of treated plants to untreated controls. Treated plants were also rated for plant damage by recording symptoms such as necrosis, chlorosis and stunting. Compounds 2 3 15 19 21 26 30 51 59 73 80 118 127 128 131 132 151 153 at 500 ppm gave more than 70% control in these trials compared to untreated checks which showed extensive disease development.

[0305] Example E: Corynespora cassiicola test on tomatoes Each compound was dissolved in 2% dimethylsulfoxide / acetone and then mixed with water containing an emulsifier to a calibrated spray volume of 30 mL. Each spray solution was poured into a spray bottle and sprayed.

[0306] To test the preventive activity of the compounds, healthy young tomato plants grown in a greenhouse were sprayed with the active compound formulations at the defined application rates in a spray cabinet using a hollow cone nozzle. One day after treatment, the plants were sprayed with 2.6 x 10 6 The plants were then inoculated with a spore suspension containing the Corynespora cassiicola inoculum. The inoculated plants were then placed in a greenhouse chamber at a temperature of 22–24°C and a relative humidity of 90–95% and examined for disease expression.

[0307] Compound performance was assessed visually by rating disease severity (on a 0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Compound efficacy (% control) was calculated by comparing disease ratings of treated plants to untreated controls. Treated plants were also assessed for plant damage by recording symptoms such as necrosis, chlorosis and stunting. Compound 64, at 500 ppm, gave more than 70% control in these tests compared to untreated checks, which showed extensive disease development.

[0308] Example F: Phytophthora infestans Test on Tomato Each compound was dissolved in 2% dimethylsulfoxide / acetone and then mixed with water containing an emulsifier to a calibrated spray volume of 30 mL. Each spray solution was poured into a spray bottle for further application.

[0309] To test the preventive activity of the compounds, healthy young tomato plants grown in a greenhouse were sprayed with the active compound formulations at the indicated application rates in a spray cabinet using a hollow cone nozzle. One day after treatment, the plants were sprayed with 0.24 × 10 6 After inoculation, the plants were kept in the dark at 15°C for 24 h and then transferred to a greenhouse chamber at a temperature of 18°C ​​and a relative humidity of 95–100% to check for disease expression.

[0310] Compound performance was assessed visually by rating disease severity (on a 0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Compound efficacy (% control) was calculated by comparing disease ratings of treated plants with untreated controls. Treated plants were also evaluated for plant damage by recording symptoms such as necrosis, chlorosis, stunting, etc. Compound 3 10 38 39 40 41 42 47 48 52 53 62 63 64 67 68 69 71 73 75 79 80 81 83 85 143 144 145 at 500 ppm gave more than 70% control in these trials compared to untreated checks which showed extensive disease development.

[0311] Example G: Phakopsora pachyrhizi Testing on Soybeans Each compound was dissolved in 2% dimethylsulfoxide / acetone and then mixed with water containing an emulsifier to a calibrated spray volume of 30 mL. Each spray solution was poured into a spray bottle and sprayed.

[0312] To test the preventive activity of the compounds, healthy young soybean plants grown in a greenhouse were sprayed with the active compound formulations at the prescribed application rates in a spray cabinet using a hollow cone nozzle. One day after treatment, 2 × 10 5 The plants were inoculated with a conidial suspension containing a Phakopsora pachyrhizi inoculum of 1000 mg / kg. The inoculated plants were then placed in a greenhouse chamber at a temperature of 22–24 °C and a relative humidity of 80–90% and examined for disease expression.

[0313] Compound performance was assessed visually by rating disease severity (0-100% scale) on treated plants 3, 7, 10, and 15 days after application. Compound efficacy (% control) was calculated by comparing disease ratings of treated plants and untreated controls. Treated plants were also assessed for plant damage by recording symptoms such as necrosis, chlorosis, and stunting. Compound 1 2 5 10 19 21 22 23 24 25 26 28 29 34 35 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 56 57 58 59 62 63 64 65 66 67 68 71 75 76 83 84 85 86 87 88 89 93 94 95 96 97 99 101 102 103 104 106 107 119 125 127 129 131 132 133 134 137 138 140 141 142 143 144 146 150 151 155 At 500 ppm, more than 70% control was obtained in these trials compared with untreated checks, which showed widespread disease development.

[0314] While the invention has been described with reference to certain preferred embodiments, other embodiments will become apparent to those skilled in the art upon review of the specification. It will be apparent to those skilled in the art that many modifications, both to materials and methods, can be practiced without departing from the scope of the invention.

Claims

1. A compound of formula (I), 【Chemistry 1】 Formula (I) In the formula, "----" indicates the presence or absence of a double bond. X is O or S; Z 1 is C(R 4 ) 1-2 , C.H.R. 4 - * CHR 4 , O- * CHR 4 , O, S or N(R 10 ) 0-1 where the carbon atom marked with "*" indicates the point of attachment to the carbon atom marked with "#"; Z 2 is C(R 4 ) 1-2 or NR 10 and; however, a) Z 1 S and Z 2 CR 4 In the case of R 5 and R 6 does not form a ring; b) Z 1 is NH and Z 2 is NH and R 3 If is oxo, R 5 and R 6 does not form a ring; c) Z 1 N and Z 2 N(CH 3 ), then R 5 and R 6 does not form a ring; R 1 is hydrogen, halogen, cyano, hydroxy, C 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 2 -C 6 -Alkenyl, C 2 -C 6 -Haloalkenyl, C 2 -C 6 -Alkynyl, C 2 -C 6 -Haloalkynyl, C 1 -C 6 -Alkoxy, C 2 -C 6 -Alkenyloxy, C 2 -C 6 -Alkynyloxy, C 1 -C 6 -Alkylthio, C 3 -C 10 -cycloalkyl and phenoxy; 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 2 -C 6 -Alkenyl, C 2 -C 6 -Haloalkenyl, C 2 -C 6 -Alkynyl, C 2 -C 6 -Haloalkynyl, C 1 -C 6 -Alkoxy, C 2 -C 6 -Alkenyloxy, C 2 -C 6 -Alkynyloxy, C 1 -C 6 -Alkylthio, C 3 -C 10 Cycloalkyl and phenoxy are optionally R 1a may be substituted with one or more groups; R 1a is halogen, cyano, C 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 2 -C 6 -Alkenyl, C 2 -C 6 -Haloalkenyl, C 2 -C 6 -Alkynyl, C 2 -C 6 -Haloalkynyl, C 1 -C 6 -Alkoxy, C 2 -C 6 -alkenyloxy and C 2 -C 6 -alkynyloxy; R 2 is hydrogen, halogen, cyano, hydroxy, C 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 2 -C 6 -Alkenyl, C 2 -C 6 -Haloalkenyl, C 2 -C 6 -Alkynyl, C 2 -C 6 -Haloalkynyl, C 1 -C 6 -Alkoxy, C 2 -C 6 -Alkenyloxy, C 2 -C 6 -Alkynyloxy, C 1 -C 6 -Alkylthio, C 3 -C 10 -cycloalkyl and phenoxy; 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 2 -C 6 -Alkenyl, C 2 -C 6 -Haloalkenyl, C 2 -C 6 -Alkynyl, C 2 -C 6 -Haloalkynyl, C 1 -C 6 -Alkoxy, C 2 -C 6 -Alkenyloxy, C 2 -C 6 -Alkynyloxy, C 1 -C 6 -Alkylthio, C 3 -C 10 Cycloalkyl and phenoxy are optionally R 2a may be substituted with one or more groups; R 2a is halogen, cyano, C 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 2 -C 6 -Alkenyl, C 2 -C 6 -Haloalkenyl, C 2 -C 6 -Alkynyl, C 2 -C 6 -Haloalkynyl, C 1 -C 6 -Alkoxy, C 2 -C 6 -alkenyloxy and C 2 -C 6 -alkynyloxy; R 3 is hydrogen, halogen, oxo, cyano, C 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 2 -C 6 -Alkenyl, C 2 -C 6 -Haloalkenyl, C 2 -C 6 -Alkynyl, C 2 -C 6 -Haloalkynyl, C 1 -C 6 -Alkoxy, C 2 -C 6 -Alkenyloxy, C 2 -C 6 -Alkynyloxy, C 1 -C 6 -Alkylthio and C 3 -C 10 -cycloalkyl; 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 2 -C 6 -Alkenyl, C 2 -C 6 -Haloalkenyl, C 2 -C 6 -Alkynyl, C 2 -C 6 -Haloalkynyl, C 1 -C 6 -Alkoxy, C 2 -C 6 -Alkenyloxy, C 2 -C 6 -Alkynyloxy, C 1 -C 6 -Alkylthio and C 3 -C 10 -cycloalkyl is optionally R 3a may be substituted with one or more groups; R 3a is hydrogen, halogen, cyano, C 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 2 -C 6 -Alkenyl, C 2 -C 6 -Haloalkenyl, C 2 -C 6 -Alkynyl, C 2 -C 6 -Haloalkynyl, C 1 -C 6 -Alkoxy, C 2 -C 6 -alkenyloxy and C 2 -C 6 -alkynyloxy; R 4 is hydrogen, halogen, cyano, C 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 2 -C 6 -Alkenyl, C 2 -C 6 -Haloalkenyl, C 2 -C 6 -Alkynyl, C 2 -C 6 -Haloalkynyl, C 1 -C 6 -Alkoxy, C 2 -C 6 -Alkenyloxy, C 2 -C 6 -Alkynyloxy, C 1 -C 6 -Alkylthio and C 3 -C 10 -cycloalkyl; 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 2 -C 6 -Alkenyl, C 2 -C 6 -Haloalkenyl, C 2 -C 6 -Alkynyl, C 2 -C 6 -Haloalkynyl, C 1 -C 6 -Alkoxy, C 2 -C 6 -Alkenyloxy, C 2 -C 6 -Alkynyloxy, C 1 -C 6 -Alkylthio and C 3 -C 10 -cycloalkyl is optionally R 4a may be substituted with one or more groups; R 4a is hydrogen, halogen, cyano, C 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 2 -C 6 -Alkenyl, C 2 -C 6 -Haloalkenyl, C 2 -C 6 -Alkynyl, C 2 -C 6 -Haloalkynyl, C 1 -C 6 -Alkoxy, C 2 -C 6 -alkenyloxy and C 2 -C 6 -alkynyloxy; R 5 and R 6 are each independently hydrogen, cyano, halogen, or C 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 2 -C 6 -Alkenyl, C 2 -C 6 -Haloalkenyl, C 2 -C 6 -Alkynyl, C 2 -C 6 -Haloalkynyl, C 1 -C 6 -Alkoxy, C 2 -C 6 -Alkenyloxy, C 2 -C 6 -Alkynyloxy, C 1 -C 6 -Alkylcarbonyl, C 1 -C 6 -Alkylthio, C 3 -C 10 -Cycloalkyl, C 3 -C 10 -Cycloalkyl-C 1 -C 6 -Alkyl and C 6 -C 10 -aryl; 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 2 -C 6 -Alkenyl, C 2 -C 6 -Haloalkenyl, C 2 -C 6 -Alkynyl, C 2 -C 6 -Haloalkynyl, C 1 -C 6 -Alkoxy, C 2 -C 6 -Alkenyloxy, C 2 -C 6 -Alkynyloxy, C 1 -C 6 -Alkylcarbonyl, C 1 -C 6 -Alkylthio, C 3 -C 10 -Cycloalkyl, C 3 -C 10 -Cycloalkyl-C 1 -C 6 -Alkyl and C 6 -C 10 -aryl is optionally R 5a or R 5 and R 6 can form, together with the atoms to which they are attached, a 3- to 6-membered non-aromatic carbocyclic or non-aromatic heterocyclic ring; one or more of the heteroatoms in said ring may be N, O or S(=O). 0-2 one or more C atoms of the ring may be optionally substituted by C(=O), C(=S); the ring may be optionally selected from R 5a may be substituted with one or more of the same or different groups; R 5a is halogen, cyano, nitro, hydroxyl, thiol, amino, C 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 1 -C 6 -Alkoxy, C 1 -C 6 -Haloalkoxy, C 1 -C 6 -Alkylthio, C 1 -C 6 -Haloalkylthio, C 3 -C 10 -cycloalkyl, and C 1 -C 6 -Alkoxy-C 1 -C 6 -alkyl; R 7 and R 8 are each independently hydrogen, cyano, halogen, hydroxy, C 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 1 -C 6 -Alkoxy, C 2 -C 6 -Alkenyloxy, C 2 -C 6 -Alkynyloxy, C 1 -C 6 -Alkylcarbonyl and C 3 -C 10 -cycloalkyl; 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 1 -C 6 -Alkoxy, C 2 -C 6 -Alkenyloxy, C 2 -C 6 -Alkynyloxy, C 1 -C 6 -Alkylcarbonyl and C 3 -C 10 -Cycloalkyl is optionally R 7a or R 7 and R 8 may together with the atoms to which they are attached form a 3- to 6-membered non-aromatic or aromatic carbocyclic or non-aromatic or aromatic heterocyclic ring; one or more of the heteroatoms in said ring may be N, O or S(=O). 0-2 one or more C atoms of the ring may optionally be replaced by C(=O) or C(=S); the ring may optionally be selected from R 7a with one or more identical or different groups; provided that R 7 and R 8 When forms an aromatic ring, R 9 does not exist; R 7a is halogen, cyano, nitro, hydroxyl, thiol, amino, C 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 1 -C 6 -Alkoxy, C 1 -C 6 -Haloalkoxy, C 1 -C 6 -Alkylthio, C 1 -C 6 -Haloalkylthio, C 3 -C 10 -cycloalkyl, and C 1 -C 6 -Alkoxy-C 1 -C 6 -alkyl; R 9 is hydrogen, halogen, C 3 -C 10 -Cycloalkyl, C 3 -C 10 -Cycloalkyloxy, C 3 -C 10 -Cycloalkenyl, C 3 -C 10 -Cycloalkenyloxy, C 6 -C 10 -aryl, C 7 -C 14 -Aralkyl, C 6 -C 10 -Aryloxy, benzyloxy, -OC(O)-C 6 -C 10 -aryl, O-C(O)-C 2 -C 10 -heterocyclyl, C 2 -C 10 -heterocyclyl and C 2 -C 10 -heterocyclooxy; provided that heterocyclyl or heterocycloxy contains 1, 2 or 3 heteroatoms selected from N, O and S; and in each case 1 or 2 CH of the carbocycle or heterocycle. 2 The group may be substituted with a group independently selected from C(=O) and C(=S); 3 -C 10 -Cycloalkyl, C 3 -C 10 -Cycloalkyloxy, C 3 -C 10 -Cycloalkenyl, C 3 -C 10 -Cycloalkenyloxy, C 6 -C 10 -aryl, C 7 -C 14 -Aralkyl, C 6 -C 10 -Aryloxy, benzyloxy, -OC(O)-C 6 -C 10 -aryl, O-C(O)-C 2 -C 10 -heterocyclyl, C 2 -C 10 -heterocyclyl and C 2 -C 10 -heterocycloxy is optionally R 9a or R 5 and R 9 can form, together with the atoms to which they are attached, a 3- to 12-membered non-aromatic carbocyclic or non-aromatic heterocyclic ring; one or more of the heteroatoms in said ring may be N, O or S(=O). 0-2 one or more C atoms of the ring may be optionally substituted by C(=O), C(=S); the ring may be optionally selected from R 9a may be substituted with one or more of the same or different groups; R 9a is hydrogen, halogen, cyano, C 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 2 -C 6 -Alkenyl, C 2 -C 6 -Haloalkenyl, C 2 -C 6 -Alkynyl, C 2 -C 6 -Haloalkynyl, C 1 -C 6 -Alkoxy, C 1 -C 6 -Haloalkoxy, C 2 -C 6 -Alkenyloxy, C 2 -C 6 -Alkynyloxy, C 3 -C 10 -Cycloalkyl, C(R'')=N-OR', C 3 -C 10 -Cycloalkyloxy, C 3 -C 10 -Cycloalkenyl, C 3 -C 10 -Cycloalkenyloxy, C 6 -C 10 -aryl, C 7 -C 14 -Aralkyl, C 6 -C 10 -aryloxy, C 2 -C 10 -heterocyclyl and C 2 -C 10 -heterocyclooxy; R' is C 1 -C 6 -Alkyl, C 2 -C 6 -Alkenyl, C 2 -C 6 -alkynyl, where each group R' is optionally selected from the group consisting of halogen, cyano, C 1 -C 6 -Alkoxy, C 3 -C 10 -Cycloalkyl, C 3 -C 10 -Cycloalkyloxy, C 6 -C 10 -aryl, C 7 -C 14 -Aralkyl and C 6 -C 10 -aryloxy; R'' is hydrogen, C 1 -C 6 -Alkyl, C 2 -C 6 -Alkenyl, C 2 -C 6 -Alkynyl, C 3 -C 10 -Cycloalkyl and C 3 -C 10 -cycloalkenyl; R 10 is hydrogen, C 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 3 -C 10 -Cycloalkyl and C 3 -C 10 -Cycloalkyl-C 1 -C 6 -alkyl; R 11 is hydrogen, C 1 -C 6 -Alkyl and C 1 -C 6 - selected from the group consisting of alkoxy; R 1 ~R 11 , R 1a ~R 5a , R 7a or R 9a Each group is optionally selected from cyano, halogen, C 1 -C 6 -Alkyl, C 2 -C 6 -Alkenyl, C 2 -C 6 -Alkynyl, C 3 -C 10 -Cycloalkyl, C 3 -C 10 -Cycloalkenyl and C 6 -C 10 -optionally substituted with one or more groups selected from aryl; compounds, or their N-oxides, metal complexes, stereoisomers, polymorphs or agriculturally acceptable salts thereof. However, the following compounds are excluded from the definition of the compound of formula (I): 2-Methyl-N-(2,4,4,trimethylpentan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(tert-butyl)-2-methyl-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(tert-butyl)-2-methyl-5,6,7,8-tetrahydroquinoline-3-carboxamide 2-Methyl-N-(2,4,4,trimethylpentan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(1-(2-chlorophenoxy)-2-cyanopropan-2-yl)-4-methyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide, N-(2-cyano-1-(5-cyano-2-(trifluoromethyl)phenoxy)propan-2-yl)-4-methyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide, N-(2-(1,2,4-oxadiazol-3-yl)propan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-cyclohexylpropan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, 3-Methyl-N-(1,1,1-trifluoro-2-methylbutan-2-yl)-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-cyclopropyl-1,1,1-trifluoropropan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, 3-Methyl-N-(4,4,4-trifluoro-2-methylbutan-2-yl)-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(4-(azepan-1-yl)-2-methylbutan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-cyclohexyl-1-hydroxypropan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-cyclopropyl-1-hydroxypropan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(1-hydroxy-2-methylbutan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(tert-butyl)-1H-imidazo[4,5-b]pyridine-6-carboxamide, N-(1-(azepan-1-yl)-2-methylpropan-2-yl)-N-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(1-(azepan-1-yl)-2-methylpropan-2-yl)-N-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-(4,5-dimethylthiazol-2-yl)propan-2-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-methyl-4-(4-methylpiperazin-1-yl) butan-2-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-(3,5-dimethylisoxazol-4-yl)propan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-(4,5-dimethylthiazol-2-yl)propan-2-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-6-carboxamide, N-(1-(3-methoxyphenyl)-2-methylpropan-2-yl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-carboxamide, N-(2-(tetrahydro-2H-pyran-4-yl)propan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(2-methyl-1-morpholinopropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(2-(1-methyl-1H-1,2,3-triazol-4-yl)propan-2-yl)thieno[3,2-b]pyridine-6-carboxamide.

2. A compound of formula (I) according to claim 1, X is O; R 1 is hydrogen, halogen, cyano, hydroxy, C 1 -C 6 -Alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 - selected from the group consisting of alkoxy; R 2 is hydrogen, halogen, cyano, hydroxy, C 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 1 -C 6 -Alkoxy, C 1 -C 6 -Alkylthio and C 3 -C 6 -cycloalkyl; R 3 is hydrogen, halogen, oxo, cyano, C 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 1 -C 6 -Alkoxy, C 1 -C 6 -Alkylthio and C 3 -C 6 -cycloalkyl; R 4 is hydrogen, halogen, cyano, C 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 1 -C 6 -Alkoxy, C 1 -C 6 -Alkylthio and C 3 -C 6 -cycloalkyl; R 5 and R 6 are each independently hydrogen, cyano, halogen, or C 1 -C 6 -Alkyl, C 2 -C 6 -Alkenyl, C 1 -C 6 -Alkoxy, C 1 -C 6 -Alkylcarbonyl, C 1 -C 6 -Alkylthio, C 3 -C 6 -Cycloalkyl, C 3 -C 6 -Cycloalkyl-C 1 -C 6 -alkyl; where R 5 and R 6 Each group is optionally R 5a or R 5 and R 6 may together with the atoms to which they are attached form a 3- to 6-membered non-aromatic carbocyclic or non-aromatic heterocyclic ring; one or more of the heteroatoms in said ring may be N, O or S(=O). 0-2 one or more C atoms of the ring may be optionally substituted by C(=O), C(=S); the ring may be optionally selected from R 5a may be substituted with one or more of the same or different groups; R 5a are halogen, cyano, nitro, hydroxyl, thiol, amino and C 1 -C 6 -alkyl; R 7 and R 8 are each independently hydrogen, cyano, halogen, hydroxy, C 1 -C 6 -Alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy, wherein C 1 -C 6 -Alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy is optionally R 7a or R 7 and R 8 can, together with the atoms to which they are attached, form a 3- to 6-membered non-aromatic or aromatic carbocyclic or non-aromatic or aromatic heterocyclic ring; one or more of the heteroatoms in said ring may be N, O or S(=O). 0-2 one or more C atoms of the ring may be optionally substituted by C(=O) or C(=S); the ring may be optionally selected from R 7a with one or more identical or different groups; provided that R 7 and R 8 When forms an aromatic ring, R 9 does not exist; R 7a is halogen, cyano, nitro, hydroxyl, thiol, amino, C 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 1 -C 6 -Alkoxy, C 1 -C 6 -Haloalkoxy, C 1 -C 6 -Alkylthio, C 1 -C 6 -Haloalkylthio, C 3 -C 8 -Cycloalkyl and C 1 -C 4 -Alkoxy-C 1 -C 4 -alkyl; R 9 is hydrogen, halogen, C 6 -C 10 -aryl, C 7 -C 14 -Aralkyl, C 6 -C 10 -Aryloxy, benzyloxy, -OC(O)-C 6 -C 10 -aryl, O-C(O)-C 2 -C 10 -heterocyclyl, C 2 -C 10 -heterocyclyl and C 2 -C 10 -heterocycloxy; heterocyclyl or heterocycloxy containing 1, 2 or 3 heteroatoms selected from N, O and S; in each case 1 or 2 CH of the carbocyclic or heterocyclic ring. 2 groups may be substituted with groups independently selected from C(=O) and C(=S); 6 -C 10 -aryl, C 7 -C 14 -Aralkyl, C 6 -C 10 -Aryloxy, benzyloxy, -OC(O)-C 6 -C 10 -aryl, O-C(O)-C 2- C 10 -heterocyclyl, C 2 -C 10 -heterocyclyl and C 2 -C 10 -heterocycloxy is optionally R 9a or R 5 and R 9 may together with the atoms to which they are attached form a 3- to 12-membered non-aromatic carbocyclic or non-aromatic heterocyclic ring; one or more of the heteroatoms in said ring may be N, O or S(=O) 0-2 one or more C atoms of the ring may be optionally substituted by C(=O), C(=S); the ring may be optionally selected from R 9a may be substituted with one or more of the same or different groups; R 9a is hydrogen, halogen, cyano, C 1 -C 6 -Alkyl, C 1 -C 6 -Haloalkyl, C 2 -C 6 -Alkenyl, C 2 -C 6 -Haloalkenyl, C 2 -C 6 -Alkynyl, C 2 -C 6 -Haloalkynyl, C 1 -C 6 -Alkoxy, C 1 -C 6 -Haloalkoxy, C 2 -C 6 -Alkenyloxy, C 2 -C 6 -Alkynyloxy, C 3 -C 6 -Cycloalkyl, C(R'')=N-OR', C 3 -C 10 -Cycloalkyloxy, C 3 -C 10 -Cycloalkenyl, C 3 -C 10 -Cycloalkenyloxy, C 6 -C 10 -aryl, C 7 -C 14 -Aralkyl, C 6 -C 10 -aryloxy, C 2 -C 10 -heterocyclyl and C 2 -C 10 -heterocyclooxy; R' is C 1 -C 6 -Alkyl, C 2 -C 6 -Alkenyl, C 2 -C 6 -alkynyl, where each group R' is optionally selected from the group consisting of halogen, cyano, C 1 -C 6 -Alkoxy, C 3 -C 6 -Cycloalkyl, C 3 -C 6 -Cycloalkyloxy, C 6 -C 10 -aryl, C 7 -C 14 -Aralkyl and C 6 -C 10 -aryloxy; R'' is hydrogen, C 1 -C 6 -Alkyl, C 2 -C 6 -Alkenyl, C 2 -C 6 -Alkynyl, C 3 -C 6 -Cycloalkyl and C 3 -C 6 -cycloalkenyl; R 10 is hydrogen, C 1 -C 4 -Alkyl, C 1 -C 4 -Haloalkyl, C 3 -C 5 -Cycloalkyl and C 3 -C 5 -Cycloalkyl-C 1 -C 3 -alkyl; and R 11 is hydrogen, C 1 -C 4 -Alkyl and C 1 -C 4 -alkoxy, compound.

3. Z 1 CH(R 4 ), and Z 2 NR 10 2. The compound of formula (I) according to claim 1,

4. Z 1 is S and Z 2 CHR 4 2. The compound of formula (I) according to claim 1,

5. Z 1 CHR 4 - * CHR 4 2. A compound of formula (I) according to claim 1, wherein: the carbon atom marked with "*" indicates the point of attachment to the carbon atom marked with "#"; 2 CHR 4 A compound.

6. Z 1 CHR 4 and Z 2 CHR 4 2. The compound of formula (I) according to claim 1,

7. Z 1 O- * CHR 4 2. A compound of formula (I) according to claim 1, wherein:

8. Z 1 NR 10 and Z 2 CHR 4 2. The compound of formula (I) according to claim 1,

9. Z 1 is O and Z 2 NR 10 and R 3 The compound of formula (I) according to claim 1, wherein is oxo.

10. The compound of formula (I) is 1-methyl-N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(3-(2-fluorophenyl)-2-methylbutan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,3-dimethyl-3-phenylbutan-2-yl)-1-methyl- 1H-Pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-1-phenylbutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(3-(2-chlorophenyl)-2-methylbutan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-3-phenylbutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-benzylcyclopentyl)-1-methyl-1 H-Pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-benzylcyclohexyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(3-chlorobenzyl)cyclohexyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(2-fluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-1-(3-(trifluoromethyl) phenyl)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(3,5-difluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-(tert-butyl)phenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(2-chlorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-isopropylphenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-1-(4-(trifluoromethoxy)phenyl)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(2,4-difluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(3 -fluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(3-chlorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(3,4-difluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(3,4-dichlorophenyl)-2-methylpropan-2-yl)-1-methyl-1H- Pyrrolo[2,3-b]pyridine-5-carboxamide, N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-(2-bromophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-1-(m-tolyl)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl) N-(2,4-dimethyl-1-phenylpentan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-thieno[3,2-b]pyridine-6-carboxamide, N-(2-methyl-1-phenylpropan-2-yl)-thieno[3,2-b]pyridine-6-carboxamide, 1,6-dimethyl-N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(3-(2-fluorophenyl)-2-methylbutan-2-yl)-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(2-fluorophenyl)-2,4-dimethylpentan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,3-dimethyl-3-phenylbutan-2-yl)-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(2-fluorophenyl)-2-methylbutan-2-yl) N-(1-benzylcyclopropyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(3-(2-chlorophenyl)-2-methylbutan-2-yl)-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-fluorophenyl)-2-methylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-chloro-3-fluorophenyl)-2-methylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide N-(1-(4-chlorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-chlorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(2-methyl-1-phenylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 3-bromo-1- Methyl-N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-chloro-2-fluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(3-bromophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(2-methoxyphenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-1-(p-tolyl)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-bromo-N-(2,4-dimethyl-1-phenylpentan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-N-(2,4-dimethyl-1-phenylpentan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-1-methyl-N-(2-methyl-1-phenyl 3-cyclopropyl-1-methyl-N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-cyclopropyl-1-methyl-N-(2,4-dimethyl-1-phenylpentan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-N,1-dimethyl-N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide 3-cyclopropyl-N,1-dimethyl-N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-bromo-N-(1-(2-fluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-N-(1-(2-fluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-cyclopropyl-N-(1-(2- Fluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-bromophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 3-bromo-N-(3-(2-fluorophenyl)-2-methylbutan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-N-(3-(2-fluorophenyl)-2-methylbutan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-cyclopropyl-N-(3-(2-fluorophenyl)-2-methylbutan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-chlorophenyl)-2-methylpropan-2-yl)-3-fluoro-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide , N-(2-methyl-1-phenylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 3-fluoro-N-(1-(2-fluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-chloro-3-fluorophenyl)-2-methylpropan-2-yl)-3-fluoro-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-fluoro-1-methyl-N-(2-methyl- 1-(p-tolyl)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(3-(2-chlorophenyl)-2-methylbutan-2-yl)-3-fluoro-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-fluoro-N-(1-(2-methoxyphenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-1H-pyrrolo[3,2-b]pyridine N-(1-(4-fluorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(4-phenylbutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,3-dihydro-1H-inden-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-1-(naphthalen-2-yl)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-2,3-dihydro-1H-inden-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-((1-phenylcyclopropyl)methyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,3-dimethyl-4-phenylbutan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-4-methyl-3,4 -dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide, 4-methyl-N-(2-methyl-1-phenylpropan-2-yl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide, 3-chloro-N-(1-(2-chlorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-bromo-N-(1-(2-chlorophenyl)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2, 3-b]pyridine-5-carboxamide, N-(1-(2-chlorophenyl)-2-methylpropan-2-yl)-3-cyclopropyl-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[3,2-b]pyridine-6-carboxamide, 3-chloro-1-methyl-N-(2-methyl-3-phenylbutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 6-methoxy-N-(2-methyl-1-phenyl N-(2,4-dimethyl-1-phenylpentan-2-yl)-6-methoxy-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-1-(4-(methylthio)phenyl)propyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 6-methoxy-1-methyl-N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-Dimethyl-1-phenylpentan-2-yl)-6-methoxy-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 6-methyl-N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-fluorophenyl)-2-methylpropan-2-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2-methyl-1-phenylpropan-2-yl)-1H-pyrrolo[3,2-b]pyridine Lysine-6-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-benzylcyclopropyl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-2-oxo-2,3-dihydrooxazolo[4,5-b]pyridine-6-carboxamide, 1,2-dimethyl-N-(2-methyl-1-phenylpropan-2-yl)- 1H-Pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,3-dimethyl-3-phenylbutan-2-yl)-1,2-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-chlorophenyl)-2-methylpropan-2-yl)-1,2-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1,2-dimethyl-N-(2-methyl-1-(p-tolyl)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1- (2-fluorophenyl)-2-methylpropan-2-yl)-1,2-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(3-hydroxy-3-methyl-1-(m-tolyl)butan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(3-hydroxy-2-methyl-4-phenylbutan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(2-cyanopropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(, tert-Butyl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-(trifluoromethyl)cyclopropyl)thieno[3,2-b]pyridine-6-carboxamide, N-(1,1,1-trifluoro-2-methylpropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1,1,1-trifluoro-2-methylbutan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-hydroxy-2-methylpropan-2-yl)thieno[3,2-b]pyridine- 6-carboxamide, N-(3-hydroxy-3-methyl-1-(m-tolyl)butan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(3-hydroxy-2-methyl-4-phenylbutan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-hydroxy-2-methyl-1-phenylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-hydroxy-2-methyl-1-phenylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide N-(1-(4-fluoro-3-methoxyphenyl)-1-hydroxy-2-methylpropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(2-ethyl-2-hydroxy-1-phenylbutyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide thieno[3,2-b]pyridine-6-carboxamide, N-(1-(4-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-(4-fluoro-3-methoxyphenyl)-1-hydroxy-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 2-methyl-2-(thieno[3,2-b]pyridine-6-carboxamide)propyl 4-fluoro-3-methoxybenzoate, 2-methyl-2-(1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide)propyl 4-fluoro-2-methylbenzoate, N-(2-ethyl-2-hydroxy-1-phenylbutyl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-(2-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N- (1-(2-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-(4-fluoro-2-methylphenyl)-1-hydroxy-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2-ethyl-1-(4-fluorophenyl)-2-hydroxybutyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2-ethyl-1-(4-fluorophenyl)-2-hydroxybutyl) N-(1-(5-fluoro-2-methylphenyl)-1-hydroxy-2-methylpropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-(2-fluorophenyl)-2-methylpent-4-en-2-yl)thieno[3,2-b]pyridine-6-carboxamide, 3-bromo-N-(1-(5-fluoro-2-methylphenyl)-1-hydroxy-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide amide, N-(1-(4-fluorophenyl)-2-hydroxy-2-methylpropyl)thieno[3,2-b]pyridine-6-carboxamide, 3-chloro-N-(2,3-dihydro-1H-inden-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-N-(2-ethyl-2-hydroxy-1-phenylbutyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(2-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-N-(1-(3,5-dichlorophenyl)cyclopropyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, (S)-N-(1,1-bis(3,5-dichlorophenyl)-1-hydroxypropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-bromo-N-(1-(2-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5- Carboxamide, 3-chloro-N-(1-(3-methoxyphenyl)cyclopropyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(2-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)-1H-pyrrolo[3,2-b]pyridine-6-carboxamide, 2-(6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide)-2-methylpropyl 3-fluorobenzoate, 2-methyl-2-(1H-pyrrolo[2,3-b]pyridine-5-carboxamide do)propyl 3-fluorobenzoate, 2-(6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamido)-2-methylpropyl 2-(trifluoromethyl)benzoate, 2-(6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamido)-2-methylpropyl 2-methylbenzoate, 2-methyl-2-(5,6,7,8-tetrahydroquinoline-3-carboxamido)propyl 2-(trifluoromethyl)benzoate, 2-methyl-2-(5,6,7,8-tetrahydroquinoline-3 -carboxamido)propyl 2-methylbenzoate, 2-methyl-2-(5,6,7,8-tetrahydroquinoline-3-carboxamido)propyl 3-fluorobenzoate, 2-(3-chloro-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamido)-2-methylpropyl 3-fluorobenzoate, N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamido, 2-methyl-2-(1H-pyrrolo[3,2-b]pyridine-6-carboxamido)propyl 3-fluorobenzoate, 2-methyl-2-(1H-pyrrolo[2,3-b]pyridine-5-carboxamido)propyl 2-(trifluoromethyl)benzoate, N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-methyl -2-(thieno[3,2-b]pyridine-6-carboxamido)propyl 2-(trifluoromethyl)benzoate, 2-methyl-2-(1H-pyrrolo[3,2-b]pyridine-6-carboxamido)propyl 2-(trifluoromethyl)benzoate, 2-methyl-2-(thieno[3,2-b]pyridine-6-carboxamido)propyl 2-methylbenzoate, N-(1-(4-fluoro-3-methoxyphenyl)-1-hydroxy-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamido 2-methyl-2-(1H-pyrrolo[2,3-b]pyridine-5-carboxamide)propyl 2-methylbenzoate, 2-methyl-2-(1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide)propyl 2-(trifluoromethyl)benzoate, 2-methyl-2-(1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide)propyl 3-fluorobenzoate, N-(1-(4-fluorophenyl)-2-hydroxy-2-methylpropyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(4-fluoro-2-methylphenyl)-1-hydroxy-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-(4-fluoro-2-methylphenyl)-1-hydroxy-2-methylpropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-(2-fluorophenoxy)-2,4-Dimethylpent-4-en-2-yl)-1H-pyrrolo[3,2-b]pyridine-6-carboxamide, 3-bromo-N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 2-(3-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine-5- carboxamido)-2-methylpropyl 3-fluorobenzoate, 3-chloro-N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 2-(3-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide)-2-methylpropyl 2-(trifluoromethyl)benzoate, N-(1-(4-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)-1-methyl-1H-pyrrolo[2, 3-b]pyridine-5-carboxamide, N-(1-(4-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)thieno[3,2-b]pyridine-6-carboxamide, 2-(3-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide)-2-methylpropyl 2-methylbenzoate, N-(1-(5-fluoro-2-methylphenyl)-1-hydroxy-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-((2- fluorobenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-((2-cyanobenzyl)oxy)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-((2-fluorobenzyl)oxy)-2-methylpropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-((2-fluorobenzyl)oxy)-2-methylpropan-2-yl)-6,7-Dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-((2-chlorobenzyl)oxy)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-((2-chlorobenzyl)oxy)-2-methylpropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-((2-cyanobenzyl)oxy)-2-methylpropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, 3-bromo-N-(1 -((2-fluorobenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-bromo-N-(1-((2-chlorobenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-bromo-N-(1-((2-cyanobenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-((2-chloro-5-fluoro N-(1-((2-chloro-5-fluorobenzyl)oxy)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-((2-chloro-5-fluorobenzyl)oxy)-2-methylpropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, N-(1-((2,4-dimethylbenzyl)oxy)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-((2,4-dimethylbenzyl)oxy)-2-methylpropan-2-yl)- 3-Bromo-N-(1-((2,4-dimethylbenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2-methyl-1-(pyridin-2-yloxy)propan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 3-Bromo-1-methyl-N-(2-methyl-1-(pyridin-2-yloxy)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-((2-chloropyridin-4-yl)oxy)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-((2-chloropyridin-4-yl)oxy)-2-methylpropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, 3-bromo-N-(1-((2-chloropyridin-4-yl)oxy)-2-methylpropan-2-yl) N-(1-((5-fluoropyridin-2-yl)oxy)-2-methylpropan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, 3-chloro-N-(1-((2-chlorobenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-N-(1-((2-cyano)oxy)-2-methylpropan-2-yl)thieno[3,2-b]pyridine-5-carboxamide 2-Chloro-N-(2-methyl-1-phenylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-Chloro-N-(2,4-dimethyl-1-phenylpentan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(2 -methyl-1-(pyridin-2-yloxy)propan-2-yl)thieno[3,2-b]pyridine-6-carboxamide, 3-chloro-N-(1-((2-fluorobenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-N-(1-((2-chloro-5-fluorobenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b], Pyridine-5-carboxamide, 3-bromo-N-(1-((5-fluoropyridin-2-yl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 2-methoxy-N-(2-methyl-1-phenylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 3-chloro-N-(1-((2,4-dimethylbenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide Pyridine-5-carboxamide, 3-chloro-1-methyl-N-(2-methyl-1-(pyridin-2-yloxy)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-N-(1-((2-chloropyridin-4-yl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-N-(1-((5-fluoropyridin-2-yl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrro 3-chloro-N-(1-((5-cyanopyridin-2-yl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-((5-cyanopyridin-2-yl)oxy)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-((5-cyanopyridin-2-yl)oxy)-2-methylpropan-2-yl)thieno[3,2- b]pyridine-6-carboxamide, 3-bromo-N-(1-((5-cyanopyridin-2-yl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-((2-chloro-5-fluorobenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-((2,5-dimethylbenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1-methyl-N-(2-methyl-1-(pyridin-2-yloxy)propan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-((2-chloropyridin-4-yl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-((5-fluoropyridin-2-yl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide amide, N-(1-((5-cyanopyridin-2-yl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-bromo-N-(1-((2-chloro-5-fluorobenzyl)oxy)-2-methylpropan-2-yl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(1-((5-fluoropyridin-2-yl)oxy)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide amide, N-(1-((2-cyanobenzyl)oxy)-2-methylpropan-2-yl)-2-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-chloro-N-(1-((2-cyanobenzyl)oxy)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-((2,4-dimethylbenzyl)oxy)-2-methylpropan-2-yl)-2-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide Boxamide, 2-chloro-N-(1-((2,4-dimethylbenzyl)oxy)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-2-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-(2-fluorophenyl)propan-2-yl)-N-methoxy-1-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 2-(2-methoxy-6,7-Dihydro-5H-cyclopenta[b]pyridine-3-carboxamide)-2-methylpropyl 3-fluorobenzoate, 2-Methoxy-N-(2-methyl-1-(pyridin-2-yloxy)propan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-Chloro-N-(2-methyl-1-(pyridin-2-yloxy)propan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-((2-chloropyridin-4-yl)oxy)-2-methylpropyl 2-chloro-N-(1-((2-chloropyridin-4-yl)oxy)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-benzylcyclopropyl)-2-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-benzylcyclopropyl)-2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine-3 -carboxamide, 2-methoxy-N-((1-phenylcyclopropyl)methyl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-chloro-N-((1-phenylcyclopropyl)methyl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-methoxy-N-(4-phenylbutan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-chloro-N-(4-phenylbutan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide Lysine-3-carboxamide, 2-chloro-N-(1-phenylcyclopropyl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-methoxy-N-(1-phenylcyclopropyl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-(2-fluorophenyl)propan-2-yl)-N-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-chloro-N-(1-(2-fluorophenyl)propan-2-yl)-N-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide7-Dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-(2-fluorophenyl)propan-2-yl)-N-methoxy-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 2-chloro-N-(1-(4-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-chloro-N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-6,7-dihydro-5H-cyclopenta[b ]pyridine-3-carboxamide, 2-(2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide)-2-methylpropyl 3-fluorobenzoate, 2-methoxy-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-chloro-N-(2-methyl-1-phenylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-chloro-N-(2,4-dimethyl-1-phenyl 2-chloro-N-(1-((2,4-dimethylbenzyl)oxy)-2-methylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-1,2-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, N-( 1-benzylcyclopropyl)-1,2-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 2-chloro-N-(1-((2-chlorobenzyl)oxy)-2-methylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-chloro-N-(1-((2-fluorobenzyl)oxy)-2-methylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-chloro-N-(1-((2-cyanobenzyl)oxy)-2-methylpropan-2-yl)-5,6,7,8-Tetrahydroquinoline-3-carboxamide, 2-chloro-N-(1-(4-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-chloro-N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(1-((2-chlorobenzyl)oxy)-2-methylpropan-2-yl)-2-methoxy-6,7-dihydro-5H-cyclopenta[b]pi Lysine-3-carboxamide, N-(1-((2-fluorobenzyl)oxy)-2-methylpropan-2-yl)-2-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-(4-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)-2-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-2-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide Ropenta[b]pyridine-3-carboxamide, N-(1-((2-chloro-5-fluorobenzyl)oxy)-2-methylpropan-2-yl)-2-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-(4-fluorophenyl)-2-methylpropan-2-yl)-1,2-dimethyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1,2-dimethyl-N-(2-phenylpropyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 1,2-dimethyl-N -((1-phenylcyclopropyl)methyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 2-chloro-N-methoxy-N-(1-phenylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 4-methyl-N-(1-phenylcyclopropyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide, N-(1-(4-fluorophenyl)cyclopropyl)-4-methyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide, 4-methyl-N-((1-phenylcyclopropyl)methyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide, N-(1-benzylcyclopropyl)-4-methyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-7-carboxamide, 2-chloro-N-(2-methyl-1-(pyridin-2-yloxy)propan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-chloro-N-(1-((2-chloropyridine 2-Chloro-N-(1-((2-chloro-5-fluorobenzyl)oxy)-2-methylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-chloro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-chloro-N-(1-((2-chloro-5-fluorobenzyl)oxy)-2-methylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-methoxy-N-(2-methyl-1-(pyridin-2-yloxy)propan 2-Methoxy-N-(2-methyl-1-phenylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-2-methoxy-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-Methoxy-N-(1-phenylcyclopropyl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-Methoxy-N-((1-phenylcyclopropyl)methyl)-5 ,6,7,8-tetrahydroquinoline-3-carboxamide, 2-methoxy-N-(4-phenylbutan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(1-(4-fluorophenyl)-2-methylpropan-2-yl)-2-methoxy-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-chloro-N-(4-phenylbutan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-chloro-N-(1-(4-fluorophenyl)-2-methylpropan-2-yl)-5,6,7,8-Tetrahydroquinoline-3-carboxamide, N-(1-(4-fluorophenyl)-2,4-dimethylpent-4-en-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(1-(2-fluorophenoxy)-2,4-dimethylpent-4-en-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(1-(4-fluorophenyl)cyclopropyl)-2 -Methoxy-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 2-chloro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 2-methoxy-N-(4 ,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 1-methyl-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 3-chloro-1-methyl-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)-1H-pyrrolo[2 ,3-b]pyridine-5-carboxamide, 3-chloro-6-methoxy-1-methyl-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide, 6,6-difluoro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(2,4-dimethyl, 4-chloro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, 4-chloro-N-(2,4-dimethyl-1-phenylpentan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 4-chloro-N-(2,4-dimethyl-1-phenylpentan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide -phenylpent-4-en-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 4-chloro-N-(2,4-dimethyl-1-phenylpentan-2-yl)-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-4-methoxy-5,6,7,8-tetrahydroquinoline-3-carboxamide, N-(2,4-dimethyl-1-phenylpentan-2-yl)-4-methoxy-6 ,7-Dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(2,4-dimethyl-1-phenylpent-4-en-2-yl)-4-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 4-chloro-N-(1-(2-fluorophenyl)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, 4-chloro-N-(1-(4-fluorophenyl)-2-methylpropan-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide 2. The compound of formula (I) according to claim 1, selected from N-(1-(2-fluorophenyl)-2-methylpropan-2-yl)-4-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-(4-fluorophenyl)-2-methylpropan-2-yl)-4-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-(4-fluorophenyl)-2-methylpropan-2-yl)-4-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide, N-(1-(4-fluorophenyl)-2-methylpropan-2-yl)-4-methoxy-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxamide,

11. A composition combining a compound of formula (I) according to claim 1 with at least one further pesticidal active substance selected from the group consisting of fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safety agents, plant growth regulators, antibiotics, fertilizers and nutrients.

12. 13. An agricultural composition comprising a compound of formula (I) as claimed in claim 1 and at least one agriculturally acceptable adjuvant selected from the group consisting of inert carriers, surfactants, additives, solid diluents and liquid diluents.

13. The composition of claim 12, wherein the composition may further comprise at least one additional active ingredient selected from the group consisting of fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safety agents, plant growth regulators, antibiotics, fertilizers and nutrients.

14. 14. The composition according to claim 13, wherein the composition is applied to seeds and the compound of formula (I) in the composition is in an amount ranging from 0.1 g ai to 10 kg ai per 100 kg of seeds.

15. A method for controlling or preventing phytopathogenic microorganisms, comprising treating the fungus, or the material, plant, plant part, locus thereof, soil or seed to be protected from fungal attack, with an effective amount of at least one compound of formula (I) as defined in claim 1, a combination as defined in claim 11, or a composition as defined in claim 12.

16. A method for controlling or preventing plant infestation by phytopathogenic microorganisms in agricultural and / or horticultural crops, comprising applying to the plant, its part or a locus an effective amount of at least one compound of formula (I) as defined in claim 1, a combination as defined in claim 11 or a composition as defined in claim 12.

17. The plant pathogenic microorganism is selected from the group consisting of wheat leaf blight (Zymoseptoria tritici), wheat leaf rust (Puccinia triticina), wheat stripe rust (Puccinia striiformis), apple scab (Venturia inaequalis), grape powdery mildew (Uncinula necator), barley scald (Rhynchosporium secalis), rice blast (Pyricularia oryzae), soybean rust (Phakopsora pachyrhizi), wheat leaf spot (Leptosphaeria nodorum), wheat powdery mildew (Blumeria graminis f. sp. tritici), barley powdery mildew (Blumeria graminis f. sp. hordei), cucumber powdery mildew (Erysiphe cichoracearum), cucumber anthracnose (Colletotrichum lagenarium), beet and soybean leaf spot (Cercospora beticola, Cercospora sojina), early blight of tomato (Alternaria solani), grey mold (Botrytis cinerea), target spot (Corynespora cassiicola), late blight of potato and tomato (Phytophthora infestans), Rhizoctonia aerial, leaf and web dieback (Rhizoctonia solani), Septoria nodorum of wheat (Parastagonospora nodorum), root rot, scab, ear rot of cereals (e.g. wheat or barley) (Fusarium culmorum), or spot of barley (Cochliobolus sativus).

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