TW202115049A - Hydroxyisoxazolines and derivatives thereof - Google Patents

Abstract

The present disclosure relates to the use of hydroxyisoxazolines and derivatives thereof as fungicides. It also relates to new hydroxyisoxazolines derivatives, their use as fungicides and compositions comprising thereof.

Description

Hydroxyisoxazoline and its derivatives (1)

The present invention relates to the use of hydroxyisoazoline and its derivatives as fungicides. The present invention also relates to novel hydroxyisoxazoline derivatives, their use as fungicides, and compositions including them.

From WO99/05130, WO2019/034602 and WO2009/051956, 3-phenylisoxazoline and its use as a herbicide or insecticide are known. It is known that isoxazole derivatives are effective as crop protection agents against or preventing microbial infections. For example, WO2015/129773 discloses isooxazole derivatives that can be used as fungicides. WO2006/031631 discloses a substituted isoxazole which can be used to control microbial hazards on plants, especially fungal hazards. Recently, it has been revealed that hydroxyisoxazoline can be effectively used to control phytopathogenic fungi (WO2018/202487).

Many fungicides have been developed so far. However, there is still a need to develop novel compounds to meet the increasing environmental and economic requirements imposed on today's crop protection agents and compositions. This includes, for example, enhancement of the spectrum of action, safety profile, selectivity, application rate, residue formation and favorable manufacturing capabilities. It is also desirable to have novel compounds that prevent the appearance of fungicide resistance.

The present invention provides novel fungicidal compounds that have advantages over known compounds and compositions in at least some of these aspects.

(I) 其中R1、R2、X、m、n和Het係如文中所述。The present invention relates to compounds of formula (I) and their salts, N-oxides and solvates:

(I) where R1, R2, X, m, n and Het are as described in the text.

The present invention relates to a composition comprising at least one compound of formula (I) as defined herein and at least one agriculturally suitable carrier.

The present invention relates to a method for controlling phytopathogenic fungi, which method comprises applying at least one compound of formula (I) as defined in the text or a composition as defined in the text to plants, plant parts, seeds, and fruits Or the step of the soil in which the plant grows.

definition

The term "alkyl" as used herein, for example, in the case of alkyl or alkylsulfinyl, alkylsulfinyl, alkylthio, and alkylamino groups, it should be understood to preferably refer to branched and non-branched chains. Branched alkyl, which refers to, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tertiary butyl, second butyl, pentyl, isopentyl, hexyl , Heptyl, octyl, nonyl and decyl and its isomers.

The term "haloalkyl" as used herein should be understood to preferably refer to branched and unbranched alkyl groups as defined above, in which one or more hydrogen substituents are replaced by halogen in the same manner or differently . Particularly preferably, the haloalkyl group is, for example, chloromethyl, fluoropropyl, fluoromethyl, difluoromethyl, trichloromethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, bromine Butyl, trifluoromethyl, iodoethyl and their isomers.

The term "alkoxy" as used herein should be understood to preferably refer to branched and unbranched alkoxy groups, meaning, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy Group, isobutoxy, tertiary butoxy, second butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyl Alkyloxy, undecyloxy and dodecyloxy and their isomers.

The term "haloalkoxy" as used herein should be understood to preferably refer to branched and unbranched alkoxy groups as defined above, in which one or more hydrogen substituents are in the same manner or differently Replaced by halogen, such as chloromethoxy, fluoromethoxy, pentafluoroethoxy, fluoropropoxy, difluoromethoxy, trichloromethoxy, 2,2,2-trifluoroethoxy, Bromobutoxy, trifluoromethoxy, iodoethoxy and its isomers.

The term "carbocyclyl" as used herein refers to a ring having 3 to 10 ring carbon atoms or 3 to 7 carbon atoms, containing non-aromatic mono- or polycyclic (fused, spiro or bridged) carbons, the carbon The cyclic group may be saturated or partially unsaturated. Examples of carbocyclic groups include cycloalkyl and cycloalkenyl groups. Examples of saturated carbocyclic groups, also referred to herein as "cycloalkyl" include, but are not limited to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl Group. Examples of partially unsaturated carbocyclic groups include, but are not limited to, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclononenyl, or cyclo Decenyl groups, where the linkage of the cycloalkyl group to the rest of the molecule can be provided by a double bond or a single bond.

The term "heterocyclyl" as used herein refers to a 3- to 10-membered group containing one to four heteroatoms independently selected from the group of oxygen, nitrogen and sulfur, preferably a 3- to 9-membered saturated or partially non- Saturated heterocycles (including mono-, bi- or tricyclic heterocycles). If the ring contains more than one oxygen atom, the oxygen atoms are not directly adjacent. Polycyclic heterocyclic groups may contain fused, spiro or bridged ring linkages. Examples of heterocyclic groups include, but are not limited to, oxiranyl, aziridinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydro Thienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazole Pyridinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl Group, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidine-3-yl, 1,2 ,4-oxadiazolidine-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazole Pyridin-3-yl, 1,3,4-oxadiazolidine-2-yl, 1,3,4-thiadiazolidine-2-yl, 1,3,4-triazolidine-2-yl, 2,3-Dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,4-dihydrofuran-2-yl, 2,4-dihydrofuran-3-yl, 2, 3-dihydrothiophen-2-yl, 2,3-dihydrothiophen-3-yl, 2,4-dihydrothiophen-2-yl, 2,4-dihydrothiophen-3-yl, 2-pyrroline -2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoazolin-3-yl, 3-isoazolin- 3-yl, 4-isoazolin-3-yl, 2-isoazolin-4-yl, 3-isoazolin-4-yl, 4-isoazolin-4-yl, 2- Isoazolin-5-yl, 3-isoazolin-5-yl, 4-isoazolin-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-dihydroazol-2 -Base, 2,3-dihydroazol-3-yl, 2,3-dihydroazol-4-yl, 2,3-dihydroazol-5-yl, 3,4-dihydroazol-5-yl -2-yl, 3,4-dihydroazol-3-yl, 3,4-dihydroazol-4-yl, 3,4-dihydroazol-5-yl, 3,4-dihydro Azol-2-yl, 3,4-dihydroazol-3-yl, 3,4-dihydroazol-4-yl, 2-piperidinyl, 3- Piperidinyl, 4-piperidinyl, 1,3-dithio-5-yl, 2-tetrahydropiperanyl, 4-tetrahydropiperanyl, 2-tetrahydrothienyl, 3-hexahydropyranyl 𠯤yl, 4-hexahydropyrimidinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperidyl, 1,3,5-hexahydropyrimidinyl-2 -Base, 1,2,4-hexahydrotri-3-yl, indol-1-yl, indol-2-yl, indol-3-yl, indol-4-yl, indole-5 -Yl, indol-6-yl, indol-7-yl, benzimidazol-1-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, indole Azol-1-yl, indazol-3-yl, indazol-4-yl, indazol-5-yl, indazol-6-yl, indazol-7-yl, indazol-2-yl, 1- Benzofuran-2-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- Benzothiophene-6-yl, 1-benzothiophen-7-yl, 1,3-benzothiazol-2-yl, 1,3-benzothiazol-4-yl, 1,3-benzothiazole- 5-yl, 1,3-benzothiazol-6-yl, 1,3-benzothiazol-7-yl, 1,3-benzothiazol-2-yl, 1,3-benzothiazol- 4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl and 1,3-benzoxazol-7-yl, 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. Unless otherwise defined elsewhere, this definition also applies to heterocyclic groups as substituents of partial constituents, such as heterocycloalkyl.

The term "halogen" or "halo" as used herein should be understood to mean fluorine, chlorine, bromine or iodine.

The term "halo" in parentheses (for example, "C ₁ -C ₆ -(halo)alkyl") refers to one or more halogen substituents that may be the same or different, if desired.

The term "alkenyl" as used herein should be understood to preferably refer to branched and unbranched alkenyl groups, such as vinyl, propen-1-yl, propen-2-yl, but-1-en-1-yl , But-1-en-2-yl, but-2-en-1-yl, but-2-en-2-yl, but-1-en-3-yl, 2-methyl-prop-2-yl En-1-yl, or 2-methyl-prop-1-en-1-yl group.

The term "alkynyl" as used herein should be understood to preferably refer to branched and unbranched alkynyl groups, such as ethynyl, prop-1-yn-1-yl, but-1-yn-1-yl, but -2-yn-1-yl or but-3-yn-1-yl group.

The term "aryl" as used herein refers to an aromatic hydrocarbon ring system comprising 6 to 15 carbon atoms, or 6 to 12 carbon atoms, preferably 6 to 10 carbon atoms. This ring system can be a monocyclic or fused polycyclic (for example, bicyclic or tricyclic) aromatic ring system. Examples of aryl groups include, but are not limited to, phenyl, azulenyl, naphthyl, and stilbyl. Please further understand that when the aryl group is substituted with one or more substituents, the (etc.) substituents can be located at any position on the aryl ring. In particular, as far as the aryl group is a phenyl group, the (etc.) substituent may occupy one or two ortho positions, one or two meta or para positions, or any combination of these positions. This definition also applies to aryl groups (for example, aryloxy) as a substituent of a part of the composition.

The term "heteroaryl" as used herein refers to an aromatic ring system containing 5 to 15 member atoms, or 5 to 12 member atoms. The carbon and one or more heteroatoms of the aromatic ring system may be the same or different O, N and S. If the ring contains more than one oxygen atom, the oxygen atoms are not directly adjacent. Heteroaryl groups can be monocyclic or polycyclic (e.g., bicyclic or tricyclic). A monocyclic heteroaryl group can have 1 to 4 heteroatoms in the ring, and a polycyclic heteroaryl ring can have 1 to 10 heteroatoms. The bicyclic heteroaryl ring may contain 8 to 15, or 8 to 12 member atoms (carbon and heteroatoms). The monocyclic heteroaryl group may contain 5 to 8 member atoms. Examples of heteroaryl groups include, but are not limited to, thienyl, furanyl, pyrrolyl, azolyl, thiazolyl, imidazolyl, pyrazolyl, isothiazolyl, isothiazolyl, ethadiazolyl, triazole Group, thiadiazolyl, thio-4H-pyrazolyl, etc., and its benzo derivatives, for example, for example, benzofuranyl, benzothienyl, benzoazolyl, benzimidazolyl, Benzotriazolyl, indazolyl, indolyl, isoindolyl, etc.; or pyridyl, titanyl, pyrimidinyl, pyridine, trisyl, etc., and its benzo derivatives, for example, for example, For example, quinolinyl, isoquinolinyl, etc.; or azacyclooctatetraenyl, indolyl, purinyl, etc., and its benzo derivatives; or quinolinyl, isoquinolinyl, quinazolinyl, Quinolinyl, naphthyridinyl, pterridinyl, carbazolyl, acridinyl, phenanthrenyl, phenothionyl, phenanthrenyl, dibenzopiperanyl, or oxyphenyl. Please further understand that in the case where the heteroaryl group is substituted with one or more substituents, the (etc.) substituents can be in any one or more positions on the heteroaryl ring. In particular, for example, in the case where the heteroaryl group is a pyridyl group, the (etc.) substituent may be positioned at one or more 2, 3, 4, 4, 3, 4, 4, 2, 3, 4, 4, 3, 4, 4, 3, 4, 3, 4, 4, 4, 4, or 4 of the nitrogen atom of the pyridyl group. 5 and/or 6 positions. This definition also applies to heteroaryl groups (for example, heteroaryloxy) as substituents of part of the constituents.

As used herein, the term "C ₁ -C ₆ ", for example, in _{the context of the definition of "C 1} -C ₆ -alkyl" or "C ₁ -C ₆ -alkoxy" should be understood to mean having 1 to A limited number of carbon atoms of 6, that is, groups of 1, 2, 3, 4, 5, or 6 carbon atoms.

The term "acyclic group" as used herein in the phrase "where the acyclic group may be substituted" refers to any non-cyclic group described in the paragraph before the word, or any non-cyclic group constituting a group cyclic portions (e.g., aryl -C ₁ -C ₈ - alkyl group of C ₁ -C ₈ - alkyl moiety).

The term "cyclic group" as used herein in the phrase "where the cyclic group may be substituted" refers to any cyclic group described in the paragraph before the word, which may be alicyclic or aromatic, or Any cyclic part of a group (for example, the aryl part of an aryl-C ₁ -C ₆ -alkyl group).

In a group containing an acyclic group and a cyclic group (for example, aryl-C ₁ -C ₆ -alkyl), each of these groups may be substituted independently of each other.

The term "leaving group" as used in the text should be understood to mean a group that is removed from a compound in a substitution or elimination reaction, such as a halogen atom, a trifluoromethanesulfonate ("trifluoromethanesulfonate") group Group, alkoxy group, methanesulfonic acid group, p-toluenesulfonic acid group, etc. Active ingredient

(I) 其中 R1  係選自由下列組成之群組：氫、C₁ -C₈ -烷基、C₃ -C₈ -環烷基、C₂ -C₈ -烯基、C₂ -C₈ -炔基、-C₁ -C₈ -烷基-芳基、-C₁ -C₈ -烷基-C₁ -C₈ -烷氧基、-Si(C₁ -C₈ -烷基)₃ 、-Si芳基(C₁ -C₈ -烷基)₂ 、-C₁ -C₈ -烷基-C₃ -C₈ -環烷基、芳基、雜芳基、-C₁ -C₈ -烷基- 雜芳基、二-C₁ -C₈ -烷基磷酸基、-C(=O)R^a 、-C(=O)N(R^a )₂ 、-C₁ -C₆ -烷基-OC(=O)R^a 和-C₁ -C₆ -烷基-C(=O)R^a ，其中R^a 係選自由下列組成之群組：氫、胺基、C₁ -C₁₀ -烷基、C₁ -C₆ -鹵烷基、C₂ -C₈ -烯基、C₂ -C₈ -鹵烯基、C₂ -C₈ -炔基、C₂ -C₈ -鹵炔基、C₁ -C₈ -烷氧基、C₁ -C₈ -鹵基烷氧基、C₁ -C₈ -烷基氫硫基、C₁ -C₈ -烷基胺基、二-C₁ -C₈ -烷基胺基、-C₁ -C₆ -烷基-C₁ -C₆ -烷氧基、C₃ -C₁₀ -碳環基、C₃ -C₁₀ -鹵基碳環基、3-至10-員雜環基、芳基、雜芳基、雜環氧基、芳氧基和雜芳氧基， 其中非環狀R1或R^a 基可經一或多個R1^a 取代基取代而其中環狀R1或R^a 基可經一或多個R1^c 取代基取代； X    為氫、氟或氯原子； m    為0、1或2； Het 為5-員雜芳基； n     為0、1、2、3或4； R2  係獨立地選自由下列組成之群組的取代基：鹵素、氰基、羥基、氫硫基(sulfanyl)、亞磺醯基、磺醯基、胺基、硝基、C₁ -C₆ -烷基、C₁ -C₆ -鹵烷基、C₁ -C₆ -羥基烷基、C₁ -C₆ -氰基烷基、C₁ -C₆ -烷氧基、C₁ -C₆ -鹵基烷氧基、C₁ -C₆ -烷基胺基、二-C₁ -C₆ -烷基胺基、C₂ -C₆ -烯基、C₂ -C₆ -鹵烯基、C₂ -C₆ -羥基烯基、C₂ -C₆ -氰基烯基、C₂ -C₆ -炔基、C₂ -C₆ -鹵炔基、C₂ -C₆ -羥基炔基、C₂ -C₆ -氰基炔基、C₁ -C₆ -烷基氫硫基、五氟-λ⁶ -氫硫基、芳基氫硫基、C₁ -C₆ -烷基亞磺醯基、芳基亞磺醯基、C₁ -C₆ -烷基磺醯基、芳基磺醯基、C₃ -C₁₀ -碳環基、3-至10-員-雜環基、芳基、雜芳基、C₃ -C₁₀ -碳環氧基、3-至10-員-雜環氧基、芳氧基、雜芳氧基、-Si(C₁ -C₆ -烷基)₃ 、-C(=O)R²¹ 、-C(=O)OR²¹ 、-C(=O)N(R²¹ )₂ 、-C(=O)N(OR²¹ )R²¹ 、-C(=O)NR²¹ N(R²¹ )₂ ,-C(=S)N(R²¹ )₂ 、-C(=NR²¹ )R²¹ 、-C(=NR²¹ )N(R²¹ )₂ 、-C(=NOR²¹ )R²¹ 、-N(R²¹ )₂ 、-NR²¹ C(=O)OR²¹ 、-N(OR²¹ )C(=O)OR²¹ 、-NR²¹ C(=O)N(R²¹ )₂ 、-NR²¹ C(=O)R²¹ 、-N(OR²¹ )C(=O)R²¹ 、-NR²¹ C(=S)R²¹ 、-NR²¹ C(=S)N(R²¹ )₂ 、-NR²¹ C(=NR²¹ )R²¹ 、-OC(=O)R²¹ 、-OC(=O)N(R²¹ )₂ 、-NR²¹ S(=O)₂ R²¹ _、 -N=CR²¹ -N(R²¹ )₂ 、-S(=O)₂ R²¹ 、-S(=O)₂ N(R²¹ )₂ 、-P(=O)(OR²¹ )₂ 、-O-C₁ -C₆ -(鹵基)烷基-芳基、-C₁ -C₆ -(鹵基)烷基-C₃ -C₁₀ -碳環基、-C₁ -C₆ -(鹵基)烷基-O-C₃ -C₁₀ -碳環基 -C₁ -C₆ -(鹵基)烷基-3-至10-員-雜環基、-C₁ -C₆ -(鹵基)烷基-O-3-至10-員-雜環基、-C₁ -C₆ -(鹵基)烷基-芳基、-C₁ -C₆ -(鹵基)烷基-雜芳基、-C₁ -C₆ -(鹵基)烷基-雜芳氧基、-C₁ -C₆ -(鹵基)烷基-OR²¹ 、-C₁ -C₆ -(鹵基)烷基-C(=O)R²¹ 、-C₁ -C₆ -(鹵基)烷基-C(=O)OR²¹ 、-C₁ -C₆ -(鹵基)烷基-C(=O)N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-C(=O)N(OR²¹ )R²¹ 、-C₁ -C₆ -(鹵基)烷基-C(=O)NR²¹ N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-C(=S)N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-C(=NR²¹ )R²¹ 、-C₁ -C₆ -(鹵基)烷基-C(=NR²¹ )N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-C(=NOH)R²¹ 、-C₁ -C₆ -(鹵基)烷基-N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ C(=O)OR²¹ 、-C₁ -C₆ -(鹵基)烷基-N(OR²¹ )C(=O)OR²¹ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ C(=O)N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ C(=O)R²¹ 、-C₁ -C₆ -(鹵基)烷基-N(OR²¹ )C(=O)R²¹ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ C(=S)R²¹ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ C(=S)N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ C(=NR²¹ )R²¹ 、-C₁ -C₆ -(鹵基)烷基-OC(=O)R²¹ 、-C₁ -C₆ -(鹵基)烷基-OC(=O)N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ S(=O)₂ R²¹ _、 -C₁ -C₆ -(鹵基)烷基-N=CR²¹ -N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-SR²¹ 、-C₁ -C₆ -(鹵基)烷基-S(=O)R²¹ 、-C₁ -C₆ -(鹵基)烷基-S(=O)OR²¹ 、-C₁ -C₆ -(鹵基)烷基-S(=O)₂ R²¹ 、-C₁ -C₆ -(鹵基)烷基-S(=O)₂ OR²¹ 、-C₁ -C₆ -(鹵基)烷基-S(=O)₂ N(R²¹ )₂ 和-C₁ -C₆ -(鹵基)烷基-P(=O)(OR²¹ )₂ ，其中 R²¹ 係獨立地選自由下列組成之群組：氫、C₁ -C₆ -(鹵基)烷基、C₃ -C₁₀ -碳環基、3-至10-員-雜環基、芳基、雜芳基和-C₁ -C₆ -(鹵基)烷基-芳基， 其中非環狀R2和R²¹ 基可經一或多個R^22a 取代基取代而環狀R2和R²¹ 基可經一或多個R^22c 取代基取代， R^1a 、R^22a 、R1^c 和R^22c 係獨立地選自由下列組成之群組：鹵素原子、硝基、羥基、氰基、羧基、胺基、氫硫基、五氟-λ⁶ -氫硫基、甲醯基、胺甲醯基、胺甲酸酯、C₁ -C₆ -烷基、C₃ -C₇ -環烷基、C₁ -C₆ -鹵烷基、C₃ -C₈ -鹵基環烷基、C₂ -C₆ -(鹵基)烯基、C₂ -C₆ -(鹵基)炔基、C₁ ‑C₆ -烷基胺基、二-C₁ ‑C₆ -烷基胺基、-Si(C₁ -C₆ -烷基)₃ 、C₁ ‑C₆ -(鹵基)烷氧基C₁ -C₆ -(鹵基)烷基氫硫基、C₁ -C₆ -(鹵基)烷基羰基、C₁ -C₆ -烷基胺甲醯基、二-C₁ -C₆ -烷基胺甲醯基、C₁ -C₆ -(鹵基)烷氧基羰基、芳氧基、C₁ ‑C₆ -(鹵基)烷基羰基氧基、C₁ ‑C₆ -(鹵基)烷基羰基胺基、C₁ -C₈ -(鹵基)烷基氫硫基、C₁ -C₈ -(鹵基)烷基亞磺醯基、C₁ -C₈ -(鹵基)烷基­磺醯基、C₁ -C₈ -烷基­磺醯基胺基、C₁ ‑C₈ -鹵烷基磺醯基胺基、胺磺醯基、C₁ ‑C₈ -烷基胺磺醯基和二-C₁ ‑C₈ -烷基胺磺醯基； 限制條件為Het不為3-乙基-1,2,4-㗁二唑-5-基；及 其限制條件為式(I)化合物不為： 3-[4-(1-甲基-1H-吡唑-5-基)苯基]-5-(三氟甲基)-4,5-二氫-1,2-㗁唑-5-醇， 3-[4-(1H-吡唑-3-基)苯基]-5-(三氟甲基)-4,5-二氫-1,2-㗁唑-5-醇， 3-[4-(1H-吡唑-4-基)苯基]-5-(三氟甲基)-4,5-二氫-1,2-㗁唑-5-醇， 3-[4-(3,5-二甲基-1,2-㗁唑-4-基)苯基]-5-(三氟甲基)-4,5-二氫-1,2-㗁唑-5-醇， 3-[4-(1,2-㗁唑-4-基)苯基]-5-(三氟甲基)-4,5-二氫-1,2-㗁唑-5-醇， 3-[4-(1-乙基-1H-吡唑-4-基)苯基]-5-(三氟甲基)-4,5-二氫-1,2-㗁唑-5-醇， 3-[4-(1-甲基-1H-吡唑-4-基)苯基]-5-(三氟甲基)-4,5-二氫-1,2-㗁唑-5-醇， 3-[4-(1-乙基-1H-吡唑-5-基)苯基]-5-(三氟甲基)-4,5-二氫-1,2-㗁唑-5-醇， 3-[4-(2-氯-1-甲基-1H-咪唑-5-基)苯基]-5-(三氟甲基)-4,5-二氫-1,2-㗁唑-5-醇， 3-[3-氟-4-(1H-咪唑-1-基)苯基]-5-(三氟甲基)-4,5-二氫-1,2-㗁唑-5-醇，及不為 3-[4-(2,5-二甲基-1H-吡咯-1-基)苯基]-5-(三氟甲基)-4,5-二氫-1,2-㗁唑-5-醇。 The present invention relates to compounds of formula (I):

(I) where R1 is selected from the group consisting of hydrogen, C ₁ -C ₈ -alkyl, C ₃ -C ₈ -cycloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C _8- Alkynyl, -C ₁ -C ₈ -alkyl-aryl, -C ₁ -C ₈ -alkyl-C ₁ -C ₈ -alkoxy, -Si(C ₁ -C ₈ -alkyl) ₃ , -Si aryl (C ₁ -C ₈ -alkyl) ₂ , -C ₁ -C ₈ -alkyl -C ₃ -C ₈ -cycloalkyl, aryl, heteroaryl, -C ₁ -C _8- Alkyl-heteroaryl, di-C ₁ -C ₈ -alkyl phosphate, -C(=O)R ^a , -C(=O)N(R ^a ) ₂ , -C ₁ -C ₆ -alkane group -OC (= O) R ^a and -C ₁ -C ₆ - alkyl -C (= O) R ^a, wherein R ^a system consisting of selected from the group consisting of: hydrogen, amino, C ₁ -C ₁₀ -Alkyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -haloalkenyl, C ₂ -C ₈ -alkynyl, C ₂ -C ₈ -haloalkynes Group, C ₁ -C ₈ -alkoxy, C ₁ -C ₈ -haloalkoxy, C ₁ -C ₈ -alkylsulfanyl, C ₁ -C ₈ -alkylamino, di-C ₁ -C ₈ -Alkylamino, -C ₁ -C ₆ -alkyl-C ₁ -C ₆ -alkoxy, C ₃ -C ₁₀ -carbocyclic group, C ₃ -C ₁₀ -halo carbocyclic ring Group, 3- to 10-membered heterocyclic group, aryl group, heteroaryl group, heterocyclic oxy group, aryloxy group and heteroaryloxy group, wherein the acyclic R1 or R ^a group may be through one or more R1 ^a and wherein the cyclic substituents R1 or R ^a group may be a ^C or more R1 substituents; X is hydrogen, fluorine or chlorine atom; m is 0, 1 or 2; Het is a 5-membered heteroaryl; n is 0, 1, 2, 3 or 4; R2 is a substituent independently selected from the group consisting of halogen, cyano, hydroxyl, sulfanyl, sulfinyl, sulfonyl, Amino, nitro, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -hydroxyalkyl, C ₁ -C ₆ -cyanoalkyl, C ₁ -C ₆ -Alkoxy, C ₁ -C ₆ -haloalkoxy, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₂ -C ₆ -alkenyl , C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ -hydroxyalkenyl, C ₂ -C ₆ -cyanoalkenyl, C ₂ -C ₆ -alkynyl, C ₂ -C ₆ -haloalkynyl , C ₂ -C ₆ -hydroxyalkynyl, C ₂ -C ₆ -cyanoalkynyl, C ₁ -C ₆ -Alkylsulfinyl, pentafluoro-λ ⁶ -sulfinyl, arylsulfinyl, C ₁ -C ₆ -alkylsulfinyl, arylsulfinyl, C ₁ -C _6- Alkylsulfonyl, arylsulfonyl, C ₃ -C ₁₀ -carbocyclic group, 3- to 10-membered-heterocyclic group, aryl, heteroaryl, C ₃ -C ₁₀ -carbocyclic group , 3- to 10-membered-heterocyclic oxy, aryloxy, heteroaryloxy, -Si(C ₁ -C ₆ -alkyl) ₃ , -C(=O)R ²¹ , -C(=O )OR ²¹ , -C(=O)N(R ²¹ ) ₂ , -C(=O)N(OR ²¹ )R ²¹ , -C(=O)NR ²¹ N(R ²¹ ) ₂ ,-C(= S)N(R ²¹ ) ₂ , -C(=NR ²¹ )R ²¹ , -C(=NR ²¹ )N(R ²¹ ) ₂ , -C(=NOR ²¹ )R ²¹ , -N(R ²¹ ) ₂ , -NR ²¹ C(=O)OR ²¹ , -N(OR ²¹ )C(=O)OR ²¹ , -NR ²¹ C(=O)N(R ²¹ ) ₂ , -NR ²¹ C(=O)R ²¹ , -N(OR ²¹ )C(=O)R ²¹ , -NR ²¹ C(=S)R ²¹ , -NR ²¹ C(=S)N(R ²¹ ) ₂ , -NR ²¹ C(=NR ²¹ )R ²¹ , -OC(=O)R ²¹ , -OC(=O)N(R ²¹ ) ₂ , -NR ²¹ S(=O) ₂ R ²¹ _, -N=CR ²¹ -N(R ²¹ ) ₂ , -S(=O) ₂ R ²¹ , -S(=O) ₂ N(R ²¹ ) ₂ , -P(=O)(OR ²¹ ) ₂ , -OC ₁ -C ₆ -(halo)alkyl -Aryl, -C ₁ -C ₆ -(halo)alkyl-C ₃ -C ₁₀ -carbocyclic group, -C ₁ -C ₆ -(halo)alkyl-OC ₃ -C _{10 -carbocyclic} Group -C ₁ -C ₆ -(halo)alkyl-3-to 10-member-heterocyclyl, -C ₁ -C ₆ -(halo)alkyl-O-3-to 10-member-hetero Cyclic, -C ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl-heteroaryl, -C ₁ -C ₆ -(halo)alkane Group-heteroaryloxy, -C ₁ -C ₆ -(halo)alkyl-OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-C(=O)R ²¹ , -C _1- C ₆ -(halo)alkyl-C(=O)OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-C(=O)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(Halo)alkyl-C(=O) N(OR ²¹ )R ²¹ , -C ₁ -C ₆ -(halo)alkyl-C(=O)NR ²¹ N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl- C(=S)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-C(=NR ²¹ )R ²¹ , -C ₁ -C ₆ -(halo)alkyl-C (=NR ²¹ )N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-C(=NOH)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-N( R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ C(=O)OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-N(OR ²¹ )C( =O)OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ C(=O)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ C(=O)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-N(OR ²¹ )C(=O)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ C(=S)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ C(=S)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl -NR ²¹ C(=NR ²¹ )R ²¹ , -C ₁ -C ₆ -(halo)alkyl-OC(=O)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-OC( =O)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ S(=O) ₂ R ²¹ _, -C ₁ -C ₆ -(halo)alkyl-N =CR ²¹ -N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-SR ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O)OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O) ₂ R ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O) ₂ OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O) ₂ N(R ²¹ ) ₂ and -C ₁ -C ₆ -(Halo)alkyl-P(=O)(OR ²¹ ) ₂ , wherein R ²¹ is independently selected from the group consisting of hydrogen, C ₁ -C ₆ -(halo)alkyl, C _3- C ₁₀ -carbocyclyl, 3- to 10-membered-heterocyclic group, aryl, heteroaryl and -C ₁ -C ₆ -(halo)alkyl-aryl, wherein acyclic R2 and The R ²¹ group may be substituted by one or more R ^22a substituents and the cyclic R2 and R ²¹ groups may be substituted by one or more R ^22c substituents. R ^1a , R ^22a , R1 ^c and R ^22c are independently selected from The following group consisting of: halogen atom, nitro group, hydroxyl group, cyano group, carboxyl group, amine group, sulfhydryl group, pentafluoro-λ ⁶ -sulfhydryl group, methionyl group, carbamethanyl group, carbamate, C ₁ -C ₆ -alkyl, C ₃ -C ₇ -cycloalkyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -halocycloalkyl, C ₂ -C ₆ -(halo )Alkenyl, C ₂ -C ₆ -(halo)alkynyl, C ₁ ‑C ₆ -alkylamino, di-C ₁ ‑C ₆ -alkylamino, -Si(C ₁ -C _6- Alkyl) ₃ , C ₁ ‑C ₆ -(halo)alkoxy C ₁ -C ₆ -(halo)alkylsulfanyl, C ₁ -C ₆ -(halo)alkylcarbonyl, C ₁ -C ₆ -Alkylamine formyl, di-C ₁ -C ₆ -alkylamine formyl, C ₁ -C ₆ -(halo)alkoxycarbonyl, aryloxy, C ₁ ‑C ₆ -(Halo)alkylcarbonyloxy group, C ₁ -C ₆ -(halo)alkylcarbonylamino group, C ₁ -C ₈ -(halo)alkyl hydrogensulfanyl group, C ₁ -C ₈ -( Halo)alkylsulfinyl, C ₁ -C ₈ -(halo)alkylsulfinyl, C ₁ -C ₈ -alkylsulfonylamino, C ₁ ‑C ₈ -haloalkylsulfonyl Amino, sulfamoyl, C ₁ ‑C ₈ -alkyl sulfamoyl and di-C ₁ ‑C ₈ -alkyl sulfamoyl; restriction is that Het is not 3-ethyl-1 ,2,4-Diazol-5-yl; and its restriction is that the compound of formula (I) is not: 3-[4-(1-methyl-1H-pyrazol-5-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol , 3-[4-(1H-pyrazol-3-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol, 3-[4-(1H-pyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol, 3-[4-(3,5-Dimethyl-1,2-oxazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-㗁Azol-5-ol, 3-[4-(1,2-oxazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol, 3-[4-(1-ethyl-1H-pyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol , 3-[4-(1-methyl-1H-pyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol , 3-[4-(1-ethyl-1H-pyrazol-5-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol , 3-[4-(2-Chloro-1-methyl-1H-imidazol-5-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole- 5-alcohol, 3-[3-Fluoro-4-(1H-imidazol-1-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol, and Not for 3-[4-(2,5-Dimethyl-1H-pyrrol-1-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole-5 -alcohol.

Compounds not included are disclosed in WO2019/122393.

The present invention includes pure stereoisomers of the compound of formula (I) and any mixtures of these isomers.

The ones not included in the text are the compounds produced by combinations that violate the laws of nature, and those who are familiar with this technology based on their professional knowledge and should be excluded. For example, ring structures with three or more adjacent oxygen atoms are excluded.

According to the nature of the substituents, the compounds of formula (I) may exist in the form of different stereoisomers. These stereoisomers include, for example, enantiomers, diastereomers, atropisomers, or geometric isomers. Therefore, the present invention includes both pure stereoisomers and any mixtures of these isomers. When a compound can exist in two or more tautomeric forms in equilibrium, the compound mentioned by the description of tautomers is deemed to include all tautomeric forms.

According to the number of double bonds in the compound, any compound of the present invention may also exist in the form of one or more geometric isomers. Geometric isomers can exist in cis (=Z-) or trans (=E-) form according to the nature of the substituents of the double bond or ring. The present invention therefore relates equally to all possible mixtures of all geometric isomers and all ratios.

The compound of formula (I) may suitably be in its free form, salt form, N-oxide form or solvate form (e.g., hydrate).

According to the nature of the substituent, the compound of formula (I) may exist in the form of a free compound and/or its salt, such as an agrochemical active salt.

Agrochemical active salts include acid addition salts of inorganic and organic acids and conventional alkali salts. Examples of inorganic acids are halogen acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfuric acid, phosphoric acid and nitric acid, and acid salts such as sodium hydrogen sulfate and potassium hydrogen sulfate. Useful organic acids include, for example, formic acid, carbonic acid, and alkanoic acid, such as acetic acid, trifluoroacetic acid, trichloroacetic acid, and propionic acid, as well as glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamon Acid, oxalic acid, saturated or unitary or dibasic unsaturated fatty acids with 6 to 20 carbon atoms, alkylsulfuric acid monoesters, alkyl sulfonic acids (sulfonic acids with linear or branched chain alkyl groups of 1 to 20 carbon atoms Acid), aryl sulfonic acid or aryl disulfonic acid (aromatic group with one or two sulfonic acid groups, such as phenyl and naphthyl), alkyl phosphonic acid (straight chain with 1 to 20 carbon atoms Or branched alkyl phosphonic acid), aryl phosphonic acid or aryl diphosphonic acid (aromatic group with one or two phosphonic acid groups, such as phenyl and naphthyl), where the alkyl and aryl groups can be further With substituents, such as p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid and the like.

The solvate of the compound of formula (I) or its salt is a stoichiometric composition of a compound with a solvent.

The compounds of formula (I) may exist in polycrystalline and/or amorphous forms. Crystal forms include unsolvated crystal forms, solvates and hydrates.

The compound of formula (I) is referred to as the "active ingredient" in the text.

In some specific examples, in the above formula (I), R1 is selected from the group consisting of hydrogen, C ₁ -C ₆ -alkyl, C ₃ -C ₈ -cycloalkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, -C ₁ -C ₆ -alkyl-aryl, -C ₁ -C ₆ -alkyl-C ₁ -C ₆ -alkoxy, -Si( C ₁ -C ₆ -alkyl) ₃ , -Si aryl (C ₁ -C ₆ -alkyl) ₂ , -C(=O)R ^a , -C(=O)N(R ^a ) ₂ ,- C ₁ -C ₆ - alkyl -OC (= O) R ^a and -C ₁ -C ₆ - alkyl -C (= O) R ^a, wherein R ^a selected from the group consisting of the group consisting of: C ₁ - C ₁₀ -alkyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -alkoxy, -C ₁ -C ₆ -Alkyl-C ₁ -C ₆ -alkoxy, C ₃ -C ₁₀ -carbocyclyl, 3- to 10-membered heterocyclyl, aryl and heteroaryl, wherein acyclic or cyclic R1 or R ^a group may be substituted as described herein.

In some specific examples, in the above formula (I), R1 is selected from the group consisting of hydrogen, C ₁ -C ₁₀ -alkyl, -Si(C ₁ -C ₆ -alkyl) ₃ , and ^{-C (= O) R a -} C 1 -C 6 - alkyl group -C (= O) R ^a, wherein R ^a selected from the group consisting of free-based: C ₁ -C ₆ - -alkyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy, -C ₁ -C ₆ -alkyl-C ₁ -C ₆ -alkoxy, C ₃ -C ₁₀ -carbocyclic, aryl And heteroaryl. Cyclic and acyclic R1 or R ^a group may be substituted as described herein.

In certain instances, in formula (I), R1 selected from the group consisting of the group consisting of: hydrogen, C ₁ -C ₆ - alkyl and -C (= O) R ^a, wherein R ^a is C ₁ -C ₆ -Alkyl (e.g. methyl). Acyclic R1 or R ^a group may be substituted as described herein.

In some specific examples, in the above formula (I), R1 is a hydrogen atom.

In some specific examples, in the above formula (I), m represents 0 or 1.

In some specific examples, in the above formula (I), m represents 1.

In some specific examples, in the above formula (I), m represents 0.

In some specific examples, in the above formula (I), Het is selected from the group consisting of furyl, thienyl, pyrrolyl, isoazolyl, isothiazolyl, pyrazolyl, and azolyl , Thiazolyl, imidazolyl, thiadiazolyl, thiadiazolyl, triazolyl and tetrazolyl. Het can be attached to the phenyl group via one of the carbon ring atoms or via the nitrogen ring member of Het (if any). Examples of 5-membered heteroaryl groups connected to a phenyl group via one of the carbon ring atoms are furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, pyrrole-2 -Base, pyrrol-3-yl, isoazol-3-yl, isoazol-4-yl, isoazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazole- 5-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, azol-2-yl, azol-4-yl, azol-5-yl, thiazole-2- Yl, thiazol-4-yl, thiazol-5-yl, imidazol-2-yl, imidazol-4-yl, 1,2,4-oxadiazole-3-yl, 1,2,4-oxadiazole- 5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4 -Diazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl and tetrazol-5-yl. Examples of 5-membered heteroaryl groups connected to phenyl via a nitrogen ring member are pyrrol-1-yl, pyrazol-1-yl, 1,2,4-triazol-1-yl, imidazole- 1-yl, 1,2,3-triazol-1-yl and 1,3,4-triazol-1-yl.

In some specific examples, in the above formula (I), Het is selected from the group consisting of furyl, thienyl, isazolyl, pyrazolyl, thiazolyl, imidazolyl, ethadiazolyl , Triazolyl and tetrazolyl.

In some specific examples, in the above formula (I), Het is selected from the group consisting of furyl, thienyl, pyrrolyl, isoazolyl, isothiazolyl, pyrazolyl, and azolyl , Thiazolyl, thiadiazolyl, thiadiazolyl, triazolyl and tetrazolyl.

In some specific examples, in the above formula (I), Het is selected from the group consisting of pyrazolyl, isothiazolyl and adiazolyl.

In some specific examples, in the above formula (I), X is a fluorine or chlorine atom.

In some specific examples, in the above formula (I), X is a fluorine atom.

In some specific examples, in the above formula (I), X is a hydrogen atom.

In some specific examples, in the above formula (I), X is a chlorine atom.

In some specific examples, in the above formula (I), R1 is a hydrogen atom and X is a fluorine atom or a chlorine atom.

In some specific examples, in the above formula (I), n represents 0, 1, or 2.

In some specific examples, in the above formula (I), n represents 0 or 1.

In some specific examples, in the above formula (I), R2 is independently selected from the group consisting of halogen, cyano, hydroxyl, sulfhydryl, amino, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -hydroxyalkyl, C ₁ -C ₆ -cyanoalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -haloalkyl Oxy, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ - alkynyl, C ₂ -C ₆ - haloalkynyl, C ₁ -C ₆ - alkyl mercapto, aryl mercapto, C ₁ -C ₆ - alkylsulfinyl acyl, aryl methylsulfoximide Aceyl, C ₁ -C ₆ -alkylsulfonyl, arylsulfonyl, C ₃ -C ₁₀ -carbocyclyl, 3- to 10-membered-heterocyclic group, aryl, heteroaryl, C _3- C ₁₀ -Carboepoxy, 3- to 10-membered-heterocyclic oxy, aryloxy, heteroaryloxy, -C(=O)R ²¹ , -C(=O)OR ²¹ ,- C(=O)N(R ²¹ ) ₂ , -C(=O)N(OR ²¹ )R ²¹ , -C(=O)NR ²¹ N(R ²¹ ) ₂ , -C(=S)N(R ²¹ ) ₂ , -C(=NOR ²¹ )R ²¹ , -N(R ²¹ ) ₂ , -NR ²¹ C(=O)OR ²¹ , -NR ²¹ C(=O)N(R ²¹ ) ₂ , -NR ²¹ C(=O)R ²¹ , -NR ²¹ C(=S)R ²¹ , -NR ²¹ C(=S)N(R ²¹ ) ₂ , -NR ²¹ C(=NR ²¹ )R ²¹ , -OC( =O)R ²¹ , -OC(=O)N(R ²¹ ) ₂ , -NR ²¹ S(=O) ₂ R ²¹ _, -S(=O) ₂ R ²¹ , -S(=O) ₂ N( R ²¹ ) ₂ , -OC ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl -C ₃ -C ₁₀ -carbocyclic group, -C _1- C ₆ -(halo)alkyl-OC ₃ -C ₁₀ -carbocyclyl-C ₁ -C ₆ -(halo)alkyl-3-to 10-membered-heterocyclyl, -C ₁ -C ₆ -(Halo)alkyl-O-3- to 10-membered-heterocyclyl, -C ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkane Group-heteroaryl, -C ₁ -C ₆ -(halo)alkyl-heteroaryloxy, -C ₁ -C ₆ -(halo)alkyl -OR ²¹ , -C ₁ -C ₆ -( Halo) alkyl-C(=O)R ²¹ 、-C ₁ -C ₆ -(halo Base) alkyl-C(=O)OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-C(=O)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo) Alkyl-C(=O)N(OR ²¹ )R ²¹ , -C ₁ -C ₆ -(halo)alkyl-C(=O)NR ²¹ N(R ²¹ ) ₂ , -C ₁ -C ₆ -(Halo)alkyl-C(=S)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo Base) alkyl-NR ²¹ C(=O)OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ C(=O)N(R ²¹ ) ₂ , -C ₁ -C _6- (Halo) alkyl-NR ²¹ C(=O)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ C(=S)R ²¹ , -C ₁ -C ₆ -(halo Base) alkyl-NR ²¹ C(=S)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-OC(=O)R ²¹ , -C ₁ -C ₆ -(halo Base) alkyl-OC(=O)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ S(=O) ₂ R ²¹ , -C ₁ -C ₆ -( Halo) alkyl-SR ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O) OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O) ₂ R ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O) ₂ OR ^{21 and-} C ₁ -C ₆ -(halo)alkyl-S(=O) ₂ N(R ²¹ ) ₂ , wherein R ²¹ is as described in the text, preferably R ²¹ is independently selected from the group consisting of : Hydrogen, C ₁ -C ₆ -(halo)alkyl, aryl, and -C ₁ -C ₆ -(halo)alkyl-aryl. The acyclic R2 and R ²¹ groups and the cyclic R2 and R ²¹ groups may be substituted as described herein.

In some specific examples, in the above formula (I), R2 is independently selected from the group consisting of halogen, cyano, C ₁ -C ₆ -alkyl (such as methyl, ethyl, propyl , Isopropyl, butyl, isobutyl), C ₁ -C ₆ -haloalkyl (e.g. trifluoromethyl, difluoromethyl), C ₁ -C ₆ -alkoxy (e.g. methoxy) , C ₁ -C ₆ -alkylamino (e.g. methylamino), two -C ₁ -C ₆ -alkylamino (e.g. dimethylamino), C ₁ -C ₆ -alkenyl (e.g. Allyl), C ₂ -C ₆ -alkynyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ -haloalkynyl, C ₁ -C ₆ -alkyl hydrogen thio (e.g. methyl hydrogen Thio group), C ₃ -C ₁₀ -carbocyclic group (preferably C ₃ -C ₆ -carbocyclic group, such as cyclopropyl, cyclopentyl), aryl (such as phenyl), heteroaryl (more Preferably a 5- or 6-membered heteroaryl group includes one or two heteroatoms, such as thienyl, pyridyl), -C(=O)R ²¹ , -C(=O)OR ²¹ , -N(R ²¹ ) _2. -OC ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl -C ₃ -C ₁₀ -carbocyclyl, -C ₁ -C _6- (Halo) alkyl-3-to 10-member-heterocyclyl, -C ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl-hetero Aryl, -C ₁ -C ₆ -(halo)alkyl-OR ²¹ and -C ₁ -C ₆ -(halo)alkyl-C(=O)OR ²¹ , wherein R ²¹ is as described in the text , Preferably R ²¹ is independently selected from the group consisting of hydrogen, C ₁ -C ₆ -(halo)alkyl, aryl and -C ₁ -C ₆ -(halo)alkyl-aryl base. The acyclic or cyclic R2 and R ²¹ groups may be substituted as described herein, preferably by halogen or C ₁ -C ₆ -(halo)alkyl.

Examples of suitable -C(=0)R ²¹ groups include -C(=0)-C ₁ -C ₆ -(halo)alkyl (e.g., methylcarbonyl).

Examples of suitable -C(=O)OR ²¹ groups include -C(=O)-OC ₁ -C ₆ -(halo)alkyl (e.g., tertiary butoxycarbonyl).

Examples of suitable -N(R ²¹ ) ₂ groups include -NH-C ₁ -C ₆ -(halo)alkyl-aryl (preferably -NH-C ₁ -C ₆ -(halo)alkyl - phenyl, e.g. -NH-CH ₂ - phenyl).

Examples of suitable -OC ₁ -C ₆ -(halo)alkyl-aryl groups include -OC ₁ -C ₆ -(halo)alkyl-phenyl (eg -O-CH ₂ -phenyl).

Examples of suitable -C ₁ -C ₆ -(halo)alkyl-aryl groups include -C ₁ -C ₆ -(halo)alkyl-phenyl (eg -CH ₂ -phenyl).

Examples of suitable -C ₁ -C ₆ -(halo)alkyl-heteroaryl groups include C ₁ -C ₆ -(halo)alkyl-heteroaryl groups, wherein the heteroaryl group is one including one or two 5 or 6-membered heteroaryl groups (e.g. thienyl, pyridyl) with six heteroatoms.

Examples of suitable -C ₁ -C ₆ -(halo)alkyl-OR ²¹ _{include -C 1} -C ₆ -(halo)alkyl-OC ₁ -C ₆ -(halo)alkyl (e.g. methyl Oxyethyl).

Examples of suitable -C ₁ -C ₆ -(halo)alkyl-C(=O)OR ²¹ _{include C 1} -C ₆ -(halo)alkyl-C(=O)OH and C ₁ -C ₆ -(Halo)alkyl-C(=O)-OC ₁ -C ₆ -(halo)alkyl.

In some specific examples, in the above formula (I), R2 is independently selected from the group consisting of fluorine, chlorine, cyano, methyl, ethyl, propyl, isopropyl, butyl, Isobutyl, trifluoromethyl, difluoromethyl, methoxy, allyl, cyclopropyl, cyclopentyl, phenyl, thienyl, pyridyl, -C(=O)H, methylcarbonyl , Tertiary butoxycarbonyl, -CH ₂ -cyclopropyl, -CH ₂ -(N-morpholinyl), -CH ₂ -phenyl (benzyl), -CH ₂ -thienyl, -CH ₂ -pyridyl, methoxyethyl, -CH ₂ -C(=O)OH, -CH ₂ -C(=O)O-methyl and -CH ₂ -C(=O)O-ethyl, Among them, the acyclic and cyclic R2 groups can be substituted with halogen or C ₁ -C ₆ -(halo)alkyl. In particular, the phenyl group may be substituted with halogen, such as fluorine or chlorine.

In some specific examples, in the above formula (I), R2 is independently _{selected from the group consisting of C 1} -C ₆ -haloalkyl, such as trifluoromethyl and difluoromethyl.

In some specific examples, in the above formula (I), Het is selected from the group consisting of furyl, thienyl, pyrrolyl, isoazolyl, isothiazolyl, pyrazolyl, azolyl , Thiazolyl, thiadiazolyl, thiadiazolyl, triazolyl and tetrazolyl.

In some of these specific examples, it is excluded where R1 is hydrogen, X is F, Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present; that is, if n=1) is a Group or ethyl compound.

In certain other such specific examples, it is excluded that R1 is hydrogen, X is F, Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present) is C ₁ -C ₆ -Alkyl compounds.

In certain other such specific examples, compounds in which Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present) is C ₁ -C ₆ -alkyl are excluded.

In some other such specific examples, compounds in which Het is pyrazolyl or oxadiazolyl, n is 0 or 1, and R2 (if any) is C ₁ -C ₆ -alkyl are excluded.

In some specific examples, in the above formula (I), n is 1, 2, 3, or 4, preferably 1 or 2, and Het is selected from the group consisting of furyl, thienyl, pyrrolyl , Isoazolyl, isothiazolyl, pyrazolyl, azolyl, thiazolyl, oxadiazolyl, thiadiazolyl, triazole and tetrazolyl, and R2 are independently selected from the group consisting of the following Group: halogen, cyano, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino , C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ -haloalkynyl, C ₁ -C ₆ -alkylsulfanyl , C ₃ -C ₁₀ -Carbocyclyl, aryl, heteroaryl, -C(=O)R ²¹ , -C(=O)OR ²¹ , -N(R ²¹ ) ₂ , -OC ₁ -C ₆ -(Halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl-C ₃ -C ₁₀ -carbocyclyl, -C ₁ -C ₆ -(halo)alkyl-3 -To 10-member-heterocyclyl, -C ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl-heteroaryl, -C ₁ -C ₆ -(halo)alkyl-OR ²¹ and -C ₁ -C ₆ -(halo)alkyl-C(=O)OR ²¹ , wherein R ²¹ is as described in the text and wherein acyclic or cyclic The R2 and R ²¹ groups may be substituted as described in claim 1. Preferably, R ²¹ is independently selected from the group consisting of hydrogen, C ₁ -C ₆ -(halo)alkyl, aryl, and -C ₁ -C ₆ -(halo)alkyl-aryl The R ² and R ²¹ groups may be substituted by halogen or C ₁ -C ₆ -(halo)alkyl.

In some specific examples, in the above formula (I), n is 1, 2, 3, or 4, preferably 1 or 2, and Het is selected from the group consisting of furyl, thienyl, pyrrolyl , Isoazolyl, isothiazolyl, pyrazolyl, azolyl, thiazolyl, oxadiazolyl, thiadiazolyl, triazole and tetrazolyl, and R2 are independently selected from the group consisting of the following Group: fluorine, chlorine, cyano, propyl, isopropyl, butyl, isobutyl, trifluoromethyl, difluoromethyl, methoxy, allyl, cyclopropyl, cyclopentyl, benzene Group, thienyl, pyridyl, -C(=O)H, methylcarbonyl, tertiary butoxycarbonyl, -CH ₂ -cyclopropyl, -CH ₂ -(N-morpholinyl), -CH ₂ -Phenyl (benzyl), -CH ₂ -thienyl, -CH ₂ -pyridyl, methoxyethyl, -CH ₂ -C(=O)OH, -CH ₂ -C(=O) O-methyl and -CH ₂ -C(=O)O-ethyl, wherein the acyclic and cyclic R2 groups can be substituted by halogen or C ₁ -C ₆ -(halo)alkyl. In particular, the phenyl group may be substituted with halogen, such as fluorine or chlorine.

The above-mentioned definitions of R1, R2, X, m, n and Het can be combined in various ways to provide subclasses of compounds according to the invention.

Non-limiting examples of subclasses of compounds include the subclasses described below.

其中 R1  係選自由下列組成之群組：氫、C₁ -C₈ -烷基、C₃ -C₈ -環烷基、C₂ -C₈ -烯基、C₂ -C₈ -炔基、-C₁ -C₈ -烷基-芳基、-C₁ -C₈ -烷基-C₁ -C₈ -烷氧基、-Si(C₁ -C₈ -烷基)₃ 、-Si芳基(C₁ -C₈ -烷基)₂ 、-C₁ -C₈ -烷基-C₃ -C₈ -環烷基、芳基、雜芳基、-C₁ -C₈ -烷基- 雜芳基、二-C₁ -C₈ -烷基磷酸基、-C(=O)R^a 、-C(=O)N(R^a )₂ 、-C₁ -C₆ -烷基-OC(=O)R^a 和-C₁ -C₆ -烷基-C(=O)R^a ，其中R^a 係選自由下列組成之群組：氫、胺基、C₁ -C₁₀ -烷基、C₁ -C₆ -鹵烷基、C₂ -C₈ -烯基、C₂ -C₈ -鹵烯基、C₂ -C₈ -炔基、C₂ -C₈ -鹵炔基、C₁ -C₈ -烷氧基、C₁ -C₈ -鹵基烷氧基、C₁ -C₈ -烷基氫硫基、C₁ -C₈ -烷基胺基、二-C₁ -C₈ -烷基胺基、-C₁ -C₆ -烷基-C₁ -C₆ -烷氧基、C₃ -C₁₀ -碳環基、C₃ -C₁₀ -鹵基碳環基、3-至10-員雜環基、芳基、雜芳基、雜環氧基、芳氧基和雜芳氧基， 其中非環狀R1或R^a 基可經一或多個R1^a 取代基取代且 其中環狀R1或R^a 基可經一或多個R1^c 取代基取代； m    為0或1； Het        係選自由下列組成之群組：呋喃基、噻吩基、吡咯基、異㗁唑基、異噻唑基、吡唑基、㗁唑基、噻唑基、咪唑基、㗁二唑基、噻二唑基、三唑基和四唑基； X    為氫、氟或氯原子； n     為0、1或2，較佳地0或1； R2  係獨立地選自由下列組成之群組：鹵素、氰基、羥基、氫硫基、胺基、C₁ -C₆ -烷基、C₁ -C₆ -鹵烷基、C₁ -C₆ -羥基烷基、C₁ -C₆ -氰基烷基、C₁ -C₆ -烷氧基、C₁ -C₆ -鹵基烷氧基、C₁ -C₆ -烷基胺基、二-C₁ -C₆ -烷基胺基、C₂ -C₆ -烯基、C₂ -C₆ -鹵烯基、C₂ -C₆ -炔基、C₂ -C₆ -鹵炔基、C₁ -C₆ -烷基氫硫基、芳基氫硫基、C₁ -C₆ -烷基亞磺醯基、芳基亞磺醯基、C₁ -C₆ -烷基磺醯基、芳基磺醯基、C₃ -C₁₀ -碳環基、3-至10-員-雜環基、芳基、雜芳基、C₃ -C₁₀ -碳環氧基、3-至10-員-雜環氧基、芳氧基、雜芳氧基、-C(=O)R²¹ 、-C(=O)OR²¹ 、-C(=O)N(R²¹ )₂ 、-C(=O)N(OR²¹ )R²¹ 、-C(=O)NR²¹ N(R²¹ )₂ 、-C(=S)N(R²¹ )₂ 、-C(=NOR²¹ )R²¹ 、-N(R²¹ )₂ 、-NR²¹ C(=O)OR²¹ 、-NR²¹ C(=O)N(R²¹ )₂ 、-NR²¹ C(=O)R²¹ 、-NR²¹ C(=S)R²¹ 、-NR²¹ C(=S)N(R²¹ )₂ 、-NR²¹ C(=NR²¹ )R²¹ 、-OC(=O)R²¹ 、-OC(=O)N(R²¹ )₂ 、-NR²¹ S(=O)₂ R²¹ _、 -S(=O)₂ R²¹ 、-S(=O)₂ N(R²¹ )₂ 、-O-C₁ -C₆ -(鹵基)烷基-芳基、-C₁ -C₆ -(鹵基)烷基-C₃ -C₁₀ -碳環基、-C₁ -C₆ -(鹵基)烷基-O-C₃ -C₁₀ -碳環基 -C₁ -C₆ -(鹵基)烷基-3-至10-員-雜環基、-C₁ -C₆ -(鹵基)烷基-O-3-至10-員-雜環基、-C₁ -C₆ -(鹵基)烷基-芳基、-C₁ -C₆ -(鹵基)烷基-雜芳基、-C₁ -C₆ -(鹵基)烷基-雜芳氧基、-C₁ -C₆ -(鹵基)烷基-OR²¹ 、-C₁ -C₆ -(鹵基)烷基-C(=O)R²¹ 、-C₁ -C₆ -(鹵基)烷基-C(=O)OR²¹ 、-C₁ -C₆ -(鹵基)烷基-C(=O)N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-C(=O)N(OR²¹ )R²¹ 、-C₁ -C₆ -(鹵基)烷基-C(=O)NR²¹ N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-C(=S)N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ C(=O)OR²¹ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ C(=O)N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ C(=O)R²¹ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ C(=S)R²¹ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ C(=S)N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-OC(=O)R²¹ 、-C₁ -C₆ -(鹵基)烷基-OC(=O)N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ S(=O)₂ R²¹ 、-C₁ -C₆ -(鹵基)烷基-SR²¹ 、-C₁ -C₆ -(鹵基)烷基-S(=O)R²¹ 、-C₁ -C₆ -(鹵基)烷基-S(=O)OR²¹ 、-C₁ -C₆ -(鹵基)烷基-S(=O)₂ R²¹ 、-C₁ -C₆ -(鹵基)烷基-S(=O)₂ OR²¹ 和-C₁ -C₆ -(鹵基)烷基-S(=O)₂ N(R²¹ )₂ ，其中R²¹ 係如文中所述，，較佳地R²¹ 係獨立地選自由下列組成之群組：氫、C₁ -C₆ -(鹵基)烷基、芳基和-C₁ -C₆ -(鹵基)烷基-芳基，其中非環狀R2和R²¹ 基可經一或多個R^22a 取代基取代而環狀R2和R²¹ 基可經一或多個R^22c 取代基取代，R^22a 和R^22c 係如文中所述。In some specific examples (the text refers to specific example Ia), the compound of the present invention is a compound of formula (I)

Wherein R1 is selected from the group consisting of hydrogen, C ₁ -C ₈ -alkyl, C ₃ -C ₈ -cycloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkynyl, -C ₁ -C ₈ -alkyl-aryl, -C ₁ -C ₈ -alkyl-C ₁ -C ₈ -alkoxy, -Si(C ₁ -C ₈ -alkyl) ₃ , -Si aryl Group (C ₁ -C ₈ -alkyl) ₂ , -C ₁ -C ₈ -alkyl -C ₃ -C ₈ -cycloalkyl, aryl, heteroaryl, -C ₁ -C ₈ -alkyl- Heteroaryl, di-C ₁ -C ₈ -alkyl phosphate, -C(=O)R ^a , -C(=O)N(R ^a ) ₂ , -C ₁ -C ₆ -alkyl-OC (= O) R ^a and -C ₁ -C ₆ - alkyl -C (= O) R ^a, wherein R ^a selected from the group consisting of the group consisting of: hydrogen, amino, C ₁ -C ₁₀ - alkyl , C ₁ -C ₆ -haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -haloalkenyl, C ₂ -C ₈ -alkynyl, C ₂ -C ₈ -haloalkynyl, C ₁ -C ₈ -Alkoxy, C ₁ -C ₈ -haloalkoxy, C ₁ -C ₈ -alkyl hydrogensulfanyl, C ₁ -C ₈ -alkylamino, di-C ₁ -C ₈ -Alkylamino, -C ₁ -C ₆ -alkyl-C ₁ -C ₆ -alkoxy, C ₃ -C ₁₀ -carbocyclic group, C ₃ -C ₁₀ -halo carbocyclic group, 3 - to 10-membered heterocyclyl, aryl, heteroaryl, heterocyclic, aryloxy, and heteroaryloxy, wherein the non-cyclic group R1 or R ^a may be substituted with one or more R1 substituents ^a and wherein R1 or R ^a cyclic group may be a ^C or more R1 substituents; m is 0 or 1; Het selected from the group consisting of the group consisting of: furyl, thienyl, pyrrolyl, oxazolyl iso㗁, Isothiazolyl, pyrazolyl, azolyl, thiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazole and tetrazolyl; X is hydrogen, fluorine or chlorine atom; n is 0, 1 or 2, preferably 0 or 1; R2 is independently selected from the group consisting of halogen, cyano, hydroxyl, sulfhydryl, amine, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -hydroxyalkyl, C ₁ -C ₆ -cyanoalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -haloalkoxy, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ -alkynyl , C ₂ -C ₆ -haloalkynyl, C ₁ -C ₆ -alkylsulfanyl, arylsulfanyl, C ₁ -C ₆ -Alkylsulfinyl, arylsulfinyl, C ₁ -C ₆ -alkylsulfinyl, arylsulfinyl, C ₃ -C ₁₀ -carbocyclic group, 3- to 10-member- Heterocyclyl, aryl, heteroaryl, C ₃ -C ₁₀ -carboepoxy, 3- to 10-membered-heterocyclic oxy, aryloxy, heteroaryloxy, -C(=O)R ²¹ , -C(=O)OR ²¹ , -C(=O)N(R ²¹ ) ₂ , -C(=O)N(OR ²¹ )R ²¹ , -C(=O)NR ²¹ N(R ²¹ ) ₂ , -C(=S)N(R ²¹ ) ₂ , -C(=NOR ²¹ )R ²¹ , -N(R ²¹ ) ₂ , -NR ²¹ C(=O)OR ²¹ , -NR ²¹ C( =O)N(R ²¹ ) ₂ , -NR ²¹ C(=O)R ²¹ , -NR ²¹ C(=S)R ²¹ , -NR ²¹ C(=S)N(R ²¹ ) ₂ , -NR ²¹ C(=NR ²¹ )R ²¹ , -OC(=O)R ²¹ , -OC(=O)N(R ²¹ ) ₂ , -NR ²¹ S(=O) ₂ R ²¹ _, -S(=O) ₂ R ²¹ , -S(=O) ₂ N(R ²¹ ) ₂ , -OC ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl-C ₃ -C ₁₀ -Carbocyclyl, -C ₁ -C ₆ -(halo)alkyl -OC ₃ -C ₁₀ -carbocyclyl -C ₁ -C ₆ -(halo)alkyl-3-to 10- Member-heterocyclyl, -C ₁ -C ₆ -(halo)alkyl-O-3- to 10-member-heterocyclyl, -C ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl-heteroaryl, -C ₁ -C ₆ -(halo)alkyl-heteroaryloxy, -C ₁ -C ₆ -(halo)alkyl -OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-C(=O)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-C(=O)OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-C(=O)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-C(=O)N(OR ²¹ )R ²¹ , -C ₁ -C ₆ -(halo)alkyl-C(=O)NR ²¹ N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-C(=S)N( R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ C(=O)OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-NR ^{2 1} C(=O)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl -NR ²¹ C(=O)R ²¹ , -C ₁ -C ₆ -(halo)alkyl -NR ²¹ C(=S)R ²¹ , -C ₁ -C ₆ -(halo)alkyl -NR ²¹ C(=S)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo) Alkyl-OC(=O)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-OC(=O)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl -NR ²¹ S(=O) ₂ R ²¹ , -C ₁ -C ₆ -(halo)alkyl-SR ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O)OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O) ₂ R ²¹ , -C _1- C ₆ -(halo)alkyl-S(=O) ₂ OR ²¹ and -C ₁ -C ₆ -(halo)alkyl-S(=O) ₂ N(R ²¹ ) ₂ , where R ²¹ is As described in the text, preferably R ²¹ is independently selected from the group consisting of hydrogen, C ₁ -C ₆ -(halo)alkyl, aryl and -C ₁ -C ₆ -(halo) ) Alkyl-aryl groups, wherein the acyclic R2 and R ²¹ groups may be substituted by one or more R ^22a substituents and the cyclic R2 and R ²¹ groups may be substituted by one or more R ^22c substituents, R ^22a and R ^22c is as described in the text.

In some specific examples, according to specific example (Ia), R2 is independently selected from the group consisting of halogen, cyano, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynes Group, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ -haloalkynyl, C ₁ -C ₆ -alkylsulfanyl, C ₃ -C ₁₀ -carbocyclyl, aryl, heteroaryl , -C(=O)R ²¹ , -C(=O)OR ²¹ , -N(R ²¹ ) ₂ , -OC ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(Halo)alkyl-C ₃ -C ₁₀ -carbocyclyl, -C ₁ -C ₆ -(halo)alkyl-3- to 10-membered-heterocyclyl, -C ₁ -C _6- (Halo) alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl-heteroaryl, -C ₁ -C ₆ -(halo)alkyl-OR ²¹ and -C ₁ -C _6- (halo)alkyl-C(=0)OR ²¹ , wherein R ²¹ is as described in the text and the acyclic or cyclic R2 and R ²¹ groups can be substituted as described in claim 1. Preferably, R ²¹ is independently selected from the group consisting of hydrogen, C ₁ -C ₆ -(halo)alkyl, aryl, and -C ₁ -C ₆ -(halo)alkyl-aryl The group, and the groups R ² and R ²¹ may be substituted with halogen or C ₁ -C ₆ -(halo)alkyl.

In some specific examples, according to specific example (Ia), R2 is independently selected from the group consisting of fluorine, chlorine, cyano, methyl, ethyl, propyl, isopropyl, butyl, isopropyl Butyl, trifluoromethyl, difluoromethyl, methoxy, allyl, cyclopropyl, cyclopentyl, phenyl, thienyl, pyridyl, -C(=O)H, methylcarbonyl, tert-butoxy carbonyl group, -CH ₂ - cyclopropyl, -CH ₂ - (N-morpholinyl it fu), - CH ₂ - phenyl (benzyl), - CH ₂ - thienyl, -CH ₂ -Pyridyl, methoxyethyl, -CH ₂ -C(=O)OH, -CH ₂ -C(=O)O-methyl and -CH ₂ -C(=O)O-ethyl, where Acyclic and cyclic R2 groups can be substituted by halogen or C ₁ -C ₆ -(halo)alkyl. In particular, the phenyl group may be substituted with halogen, such as fluorine or chlorine.

In some specific examples, according to specific example (Ia), Het is selected from the group consisting of furyl, thienyl, pyrrolyl, isoazolyl, isothiazolyl, pyrazolyl, azolyl, Thiazolyl, thiadiazolyl, thiadiazolyl, triazolyl and tetrazolyl. In some of these specific examples, compounds in which R1 is hydrogen, X is F, Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present) is methyl or ethyl are excluded . In certain other such specific examples, it is excluded that R1 is hydrogen, X is F, Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present) is C ₁ -C ₆ -Alkyl compounds. In certain other such specific examples, compounds in which Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present) is C ₁ -C ₆ -alkyl are excluded. In some other such specific examples, compounds in which Het is pyrazolyl or oxadiazolyl, n is 0 or 1, and R2 (if any) is C ₁ -C ₆ -alkyl are excluded.

In some specific examples, according to specific example (Ia), n is 1 or 2, and Het is selected from the group consisting of furyl, thienyl, pyrrolyl, isooxazolyl, isothiazolyl, pyrazole Group, azolyl, thiazolyl, azodiazolyl, thiadiazolyl, triazolyl and tetrazolyl, and R2 is independently selected from the group consisting of halogen, cyano, C ₁ -C ₆ -Haloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ -haloalkynyl, C ₁ -C ₆ -alkyl hydrogensulfanyl, C ₃ -C ₁₀ -carbocyclyl, aromatic Group, heteroaryl, -C(=O)R ²¹ , -C(=O)OR ²¹ , -N(R ²¹ ) ₂ , -OC ₁ -C ₆ -(halo)alkyl-aryl,- C ₁ -C ₆ -(halo)alkyl-C ₃ -C ₁₀ -carbocyclyl, -C ₁ -C ₆ -(halo)alkyl-3- to 10-membered-heterocyclyl, -C ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl-heteroaryl, -C ₁ -C ₆ -(halo)alkyl-OR ²¹ and -C ₁ -C ₆ -(halo)alkyl-C(=O)OR ²¹ , wherein R ²¹ is as described in the text and wherein acyclic or cyclic R2 and R ²¹ groups may be substituted as described in the text . Preferably, R ²¹ is independently selected from the group consisting of hydrogen, C ₁ -C ₆ -(halo)alkyl, aryl and -C ₁ -C ₆ -(halo)alkyl-aryl The group, and the groups R ² and R ²¹ may be substituted with halogen or C ₁ -C ₆ -(halo)alkyl.

In some specific examples, according to specific example (Ia), n is 1 or 2, and Het is selected from the group consisting of furyl, thienyl, pyrrolyl, isooxazolyl, isothiazolyl, pyrazole Group, azolyl, thiazolyl, oxadiazolyl, thiadiazolyl, triazolyl and tetrazolyl, and R2 is independently selected from the group consisting of fluorine, chlorine, cyano, propyl, Isopropyl, butyl, isobutyl, trifluoromethyl, difluoromethyl, methoxy, allyl, cyclopropyl, cyclopentyl, phenyl, thienyl, pyridyl, -C(= O)H, methylcarbonyl, tertiary butoxycarbonyl, -CH ₂ -cyclopropyl, -CH ₂ -(N-morpholinyl), -CH ₂ -phenyl (benzyl), -CH ₂ -Thienyl, -CH ₂ -pyridyl, methoxyethyl, -CH ₂ -C(=O)OH, -CH ₂ -C(=O)O-methyl and -CH ₂ -C(= O) O-Ethyl group, wherein the acyclic and cyclic R2 groups can be substituted by halogen or C ₁ -C ₆ -(halo)alkyl. In particular, the phenyl group may be substituted with halogen, such as fluorine or chlorine.

其中 R1 係由下列之群組中選出：氫、C₁ -C₆ -烷基、-Si(C₁ -C₆ -烷基)₃ 、-C(=O)R^a ,和-C₁ -C₆ -烷基-C(=O)R^a ，其中R^a 係選自由下列組成之群組：C₁ -C₁₀ -烷基、C₁ -C₆ -鹵烷基、C₁ -C₆ -烷氧基、-C₁ -C₆ -烷基-C₁ -C₆ -烷氧基、C₃ -C₁₀ -碳環基、芳基和雜芳基， 其中非環狀R1或R^a 基可經一或多個R1^a 取代基取代而其中環狀R1或R^a 基可經一或多個R1^c 取代基取代；R^1a 和R^1c 係如文中所揭示， m   為0或1； Het係選自由下列組成之群組：呋喃基、噻吩基、異㗁唑基、吡唑基、噻唑基、咪唑基、㗁二唑基、三唑基和四唑基； X   為氫、氟或氯原子； n    為0、1或2，較佳地0或1； R2  係獨立地選自由下列組成之群組：鹵素、氰基、羥基、氫硫基、胺基、C₁ -C₆ -烷基、C₁ -C₆ -鹵烷基、C₁ -C₆ -羥基烷基、C₁ -C₆ -氰基烷基、C₁ -C₆ -烷氧基、C₁ -C₆ -鹵基烷氧基、C₁ -C₆ -烷基胺基、二-C₁ -C₆ -烷基胺基、C₂ -C₆ -烯基、C₂ -C₆ -鹵烯基、C₂ -C₆ -炔基、C₂ -C₆ -鹵炔基、C₁ -C₆ -烷基氫硫基、芳基氫硫基、C₁ -C₆ -烷基亞磺醯基、芳基亞磺醯基、C₁ -C₆ -烷基磺醯基、芳基磺醯基、C₃ -C₁₀ -碳環基、3-至10-員-雜環基、芳基、雜芳基、C₃ -C₁₀ -碳環氧基、3-至10-員-雜環氧基、芳氧基、雜芳氧基、-C(=O)R²¹ 、-C(=O)OR²¹ 、-C(=O)N(R²¹ )₂ 、-C(=O)N(OR²¹ )R²¹ 、-C(=O)NR²¹ N(R²¹ )₂ 、-C(=S)N(R²¹ )₂ 、-C(=NOR²¹ )R²¹ 、-N(R²¹ )₂ 、-NR²¹ C(=O)OR²¹ 、-NR²¹ C(=O)N(R²¹ )₂ 、-NR²¹ C(=O)R²¹ 、-NR²¹ C(=S)R²¹ 、-NR²¹ C(=S)N(R²¹ )₂ 、-NR²¹ C(=NR²¹ )R²¹ 、-OC(=O)R²¹ 、-OC(=O)N(R²¹ )₂ 、-NR²¹ S(=O)₂ R²¹ _、 -S(=O)₂ R²¹ 、-S(=O)₂ N(R²¹ )₂ 、-O-C₁ -C₆ -(鹵基)烷基-芳基、-C₁ -C₆ -(鹵基)烷基-C₃ -C₁₀ -碳環基、-C₁ -C₆ -(鹵基)烷基-O-C₃ -C₁₀ -碳環基 -C₁ -C₆ -(鹵基)烷基-3-至10-員-雜環基、-C₁ -C₆ -(鹵基)烷基-O-3-至10-員-雜環基、-C₁ -C₆ -(鹵基)烷基-芳基、-C₁ -C₆ -(鹵基)烷基-雜芳基、-C₁ -C₆ -(鹵基)烷基-雜芳氧基、-C₁ -C₆ -(鹵基)烷基-OR²¹ 、-C₁ -C₆ -(鹵基)烷基-C(=O)R²¹ 、-C₁ -C₆ -(鹵基)烷基-C(=O)OR²¹ 、-C₁ -C₆ -(鹵基)烷基-C(=O)N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-C(=O)N(OR²¹ )R²¹ 、-C₁ -C₆ -(鹵基)烷基-C(=O)NR²¹ N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-C(=S)N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ C(=O)OR²¹ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ C(=O)N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ C(=O)R²¹ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ C(=S)R²¹ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ C(=S)N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-OC(=O)R²¹ 、-C₁ -C₆ -(鹵基)烷基-OC(=O)N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ S(=O)₂ R²¹ 、-C₁ -C₆ -(鹵基)烷基-SR²¹ 、-C₁ -C₆ -(鹵基)烷基-S(=O)R²¹ 、-C₁ -C₆ -(鹵基)烷基-S(=O)OR²¹ 、-C₁ -C₆ -(鹵基)烷基-S(=O)₂ R²¹ 、-C₁ -C₆ -(鹵基)烷基-S(=O)₂ OR²¹ 和-C₁ -C₆ -(鹵基)烷基-S(=O)₂ N(R²¹ )₂ ，其中R²¹ 係如文中所述，較佳地R²¹ 係獨立地選自由下列組成之群組：氫、C₁ -C₆ -(鹵基)烷基、芳基和-C₁ -C₆ -(鹵基)烷基-芳基， 其中非環狀R2和R²¹ 基可經一或多個R^22a 取代基取代而環狀R2和R²¹ 基可經一或多個R^22c 取代基取代，R^22a 和R^22c 係如文中所述。In some specific examples (the text refers to specific example Ib), the compound of the present invention is a compound of formula (I)

Where R1 is selected from the following group: hydrogen, C ₁ -C ₆ -alkyl, -Si(C ₁ -C ₆ -alkyl) ₃ , -C(=O)R ^a , and -C _1- C ₆ - alkyl -C (= O) R ^a, wherein R ^a selected from the group consisting of the group consisting of: C ₁ -C ₁₀ - alkyl, C ₁ -C ₆ - haloalkyl, C ₁ -C ₆ - alkoxy, -C ₁ -C ₆ - alkyl -C ₁ -C ₆ - alkoxy, C ₃ -C ₁₀ - carbocyclic group, aryl and heteroaryl, wherein R ^a or acyclic R1 may be a group ^a or more substituents R1 and wherein R1 or R ^a cyclic group may be a ^C or more R1 substituents; R ^1a and R ^1c lines as disclosed herein, m is 0 or 1; Het is selected from the group consisting of furyl, thienyl, isoazolyl, pyrazolyl, thiazolyl, imidazolyl, oxadiazolyl, triazolyl and tetrazolyl; X is hydrogen, fluorine or Chlorine atom; n is 0, 1 or 2, preferably 0 or 1; R2 is independently selected from the group consisting of halogen, cyano, hydroxyl, sulfhydryl, amine, C ₁ -C _6- Alkyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -hydroxyalkyl, C ₁ -C ₆ -cyanoalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C _6- Haloalkoxy, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ - alkynyl, C ₂ -C ₆ - haloalkynyl, C ₁ -C ₆ - alkyl mercapto, aryl mercapto, C ₁ -C ₆ - alkylsulfinyl acyl, aryl Sulfinyl, C ₁ -C ₆ -alkylsulfonyl, arylsulfonyl, C ₃ -C ₁₀ -carbocyclyl, 3- to 10-membered-heterocyclic group, aryl, heteroaryl Group, C ₃ -C ₁₀ -carboepoxy, 3- to 10-member-heterocyclic oxy, aryloxy, heteroaryloxy, -C(=O)R ²¹ , -C(=O)OR ²¹ , -C(=O)N(R ²¹ ) ₂ , -C(=O)N(OR ²¹ )R ²¹ , -C(=O)NR ²¹ N(R ²¹ ) ₂ , -C(=S) N(R ²¹ ) ₂ , -C(=NOR ²¹ )R ²¹ , -N(R ²¹ ) ₂ , -NR ²¹ C(=O)OR ²¹ , -NR ²¹ C(=O)N(R ²¹ ) ₂ , -NR ²¹ C(=O)R ²¹ , -NR ²¹ C(=S)R ²¹ , -NR ²¹ C(=S)N(R ²¹ ) ₂ , -NR ²¹ C(=NR ²¹ )R ²¹ , -OC(=O)R ²¹ , -OC(=O)N(R ²¹ ) ₂ , -NR ²¹ S(=O) ₂ R ²¹ _, -S(=O) ₂ R ²¹ , -S(=O) ₂ N(R ²¹ ) ₂ , -OC ₁ -C ₆ -(halo )Alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl-C ₃ -C ₁₀ -carbocyclyl, -C ₁ -C ₆ -(halo)alkyl-OC ₃ -C ₁₀ -Carbocyclyl-C ₁ -C ₆ -(halo)alkyl-3-to 10-membered-heterocyclyl, -C ₁ -C ₆ -(halo)alkyl-O-3-to 10- Member-heterocyclyl, -C ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl-heteroaryl, -C ₁ -C ₆ -(halo) Group) alkyl-heteroaryloxy, -C ₁ -C ₆ -(halo)alkyl-OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-C(=O)R ²¹ ,- C ₁ -C ₆ -(halo)alkyl-C(=O)OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-C(=O)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(Halo)alkyl-C(=O)N(OR ²¹ )R ²¹ , -C ₁ -C ₆ -(Halo)alkyl-C(=O)NR ²¹ N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-C(=S)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-N(R ²¹ ) ₂ ,- C ₁ -C ₆ -(halo)alkyl-NR ²¹ C(=O)OR ²¹ 、-C ₁ -C ₆ -(halo)alkyl-NR ²¹ C(=O)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ C(=O)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ C(=S)R ²¹ ,- C ₁ -C ₆ -(halo)alkyl-NR ²¹ C(=S)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-OC(=O)R ²¹ ,- C ₁ -C ₆ -(halo)alkyl-OC(=O)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ S(=O) ₂ R ²¹ , -C ₁ -C ₆ -(halo)alkyl-SR ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O)R ²¹ , -C ₁ -C ₆ -(halo) Alkyl-S(=O)OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O) ₂ R ²¹ , -C ₁ -C ₆ -(halo)alkyl-S( =O) ₂ OR ²¹ and -C ₁ -C ₆ -(halo) Alkyl-S(=O) ₂ N(R ²¹ ) ₂ , wherein R ²¹ is as described in the text, preferably R ²¹ is independently selected from the group consisting of hydrogen, C ₁ -C ₆ -( Halo) alkyl, aryl and -C ₁ -C ₆ -(halo)alkyl-aryl, wherein the acyclic R2 and R ²¹ groups may be substituted by one or more R ^22a substituents and cyclic R2 The and R ²¹ groups may be substituted with one or more R ^22c substituents, and R ^22a and R ^22c are as described in the text.

其中 R1 係選自由下列組成之群組：氫、C₁ -C₆ -烷基和–C(=O)R^a ，其中R^a 為C₁ -C₆ -烷基(例如甲基)； m   為0或1； Het       係選自由下列組成之群組：呋喃基、噻吩基、異㗁唑基、吡唑基、噻唑基、咪唑基、㗁二唑基、三唑基和四唑基； X   為氫、氟或氯原子； n    為0、1或2，較佳地0或1； R2 係獨立地選自由下列組成之群組：鹵素、氰基、羥基、氫硫基、胺基、C₁ -C₆ -烷基、C₁ -C₆ -鹵烷基、C₁ -C₆ -羥基烷基、C₁ -C₆ -氰基烷基、C₁ -C₆ -烷氧基、C₁ -C₆ -鹵基烷氧基、C₁ -C₆ -烷基胺基、二-C₁ -C₆ -烷基胺基、C₂ -C₆ -烯基、C₂ -C₆ -鹵烯基、C₂ -C₆ -炔基、C₂ -C₆ -鹵炔基、C₁ -C₆ -烷基氫硫基、芳基氫硫基、C₁ -C₆ -烷基亞磺醯基、芳基亞磺醯基、C₁ -C₆ -烷基磺醯基、芳基磺醯基、C₃ -C₁₀ -碳環基、3-至10-員-雜環基、芳基、雜芳基、C₃ -C₁₀ -碳環氧基、3-至10-員-雜環氧基、芳氧基、雜芳氧基、-C(=O)R²¹ 、-C(=O)OR²¹ 、-C(=O)N(R²¹ )₂ 、-C(=O)N(OR²¹ )R²¹ 、-C(=O)NR²¹ N(R²¹ )₂ 、-C(=S)N(R²¹ )₂ 、-C(=NOR²¹ )R²¹ 、-N(R²¹ )₂ 、-NR²¹ C(=O)OR²¹ 、-NR²¹ C(=O)N(R²¹ )₂ 、-NR²¹ C(=O)R²¹ 、-NR²¹ C(=S)R²¹ 、-NR²¹ C(=S)N(R²¹ )₂ 、-NR²¹ C(=NR²¹ )R²¹ 、-OC(=O)R²¹ 、-OC(=O)N(R²¹ )₂ 、-NR²¹ S(=O)₂ R²¹ _、 -S(=O)₂ R²¹ 、-S(=O)₂ N(R²¹ )₂ 、-O-C₁ -C₆ -(鹵基)烷基-芳基、-C₁ -C₆ -(鹵基)烷基-C₃ -C₁₀ -碳環基、-C₁ -C₆ -(鹵基)烷基-O-C₃ -C₁₀ -碳環基 -C₁ -C₆ -(鹵基)烷基-3-至10-員-雜環基、-C₁ -C₆ -(鹵基)烷基-O-3-至10-員-雜環基、-C₁ -C₆ -(鹵基)烷基-芳基、-C₁ -C₆ -(鹵基)烷基-雜芳基、-C₁ -C₆ -(鹵基)烷基-雜芳氧基、-C₁ -C₆ -(鹵基)烷基-OR²¹ 、-C₁ -C₆ -(鹵基)烷基-C(=O)R²¹ 、-C₁ -C₆ -(鹵基)烷基-C(=O)OR²¹ 、-C₁ -C₆ -(鹵基)烷基-C(=O)N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-C(=O)N(OR²¹ )R²¹ 、-C₁ -C₆ -(鹵基)烷基-C(=O)NR²¹ N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-C(=S)N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ C(=O)OR²¹ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ C(=O)N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ C(=O)R²¹ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ C(=S)R²¹ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ C(=S)N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-OC(=O)R²¹ 、-C₁ -C₆ -(鹵基)烷基-OC(=O)N(R²¹ )₂ 、-C₁ -C₆ -(鹵基)烷基-NR²¹ S(=O)₂ R²¹ 、-C₁ -C₆ -(鹵基)烷基-SR²¹ 、-C₁ -C₆ -(鹵基)烷基-S(=O)R²¹ 、-C₁ -C₆ -(鹵基)烷基-S(=O)OR²¹ 、-C₁ -C₆ -(鹵基)烷基-S(=O)₂ R²¹ 、-C₁ -C₆ -(鹵基)烷基-S(=O)₂ OR²¹ 和-C₁ -C₆ -(鹵基)烷基-S(=O)₂ N(R²¹ )₂ ，其中R²¹ 係如文中所述，較佳地R²¹ 係獨立地選自由下列組成之群組：氫、C₁ -C₆ -(鹵基)烷基、芳基和-C₁ -C₆ -(鹵基)烷基-芳基， 其中非環狀R2和R²¹ 基可經一或多個R^22a 取代基取代而環狀R2和R²¹ 基可經一或多個R^22c 取代基取代，R^22a 和R^22c 係如文中所述。In some specific examples (the text refers to specific example Ic), the compound of the present invention is a compound of formula (I)

Wherein R1 is selected from the group consisting of the group consisting of: hydrogen, C ₁ -C ₆ - alkyl and -C (= O) R ^a, wherein R ^a is C ₁ -C ₆ - alkyl (e.g. methyl); m Is 0 or 1; Het is selected from the group consisting of furyl, thienyl, isoazolyl, pyrazolyl, thiazolyl, imidazolyl, ethadiazolyl, triazolyl and tetrazolyl; X Is hydrogen, fluorine or chlorine atom; n is 0, 1 or 2, preferably 0 or 1; R2 is independently selected from the group consisting of halogen, cyano, hydroxyl, sulfhydryl, amine, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -hydroxyalkyl, C ₁ -C ₆ -cyanoalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -haloalkoxy, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₂ -C ₆ -alkenyl, C ₂ -C _6- Haloalkenyl, C ₂ -C ₆ -alkynyl, C ₂ -C ₆ -haloalkynyl, C ₁ -C ₆ -alkylsulfanyl, arylsulfanyl, C ₁ -C ₆ -alkylene Sulfonyl, arylsulfinyl, C ₁ -C ₆ -alkylsulfonyl, arylsulfonyl, C ₃ -C ₁₀ -carbocyclic group, 3- to 10-membered-heterocyclic group, Aryl, heteroaryl, C ₃ -C ₁₀ -carboepoxy, 3- to 10-membered-heterocyclic oxy, aryloxy, heteroaryloxy, -C(=O)R ²¹ , -C (=O)OR ²¹ , -C(=O)N(R ²¹ ) ₂ , -C(=O)N(OR ²¹ )R ²¹ , -C(=O)NR ²¹ N(R ²¹ ) ₂ ,- C(=S)N(R ²¹ ) ₂ , -C(=NOR ²¹ )R ²¹ , -N(R ²¹ ) ₂ , -NR ²¹ C(=O)OR ²¹ , -NR ²¹ C(=O)N (R ²¹ ) ₂ , -NR ²¹ C(=O)R ²¹ , -NR ²¹ C(=S)R ²¹ , -NR ²¹ C(=S)N(R ²¹ ) ₂ , -NR ²¹ C(=NR ²¹ )R ²¹ , -OC(=O)R ²¹ , -OC(=O)N(R ²¹ ) ₂ , -NR ²¹ S(=O) ₂ R ²¹ _, -S(=O) ₂ R ²¹ ,- S(=O) ₂ N(R ²¹ ) ₂ , -OC ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl-C ₃ -C _10- Carbocyclyl, -C ₁ -C ₆ -(halo)alkyl-OC ₃ -C ₁₀ -carbocyclyl-C ₁ -C ₆ -(halo)alkyl-3-to 10-member-heterocycle Base, -C ₁ -C ₆ -( Halo) alkyl-O-3- to 10-member-heterocyclic group, -C ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl- Heteroaryl, -C ₁ -C ₆ -(halo)alkyl-heteroaryloxy, -C ₁ -C ₆ -(halo)alkyl -OR ²¹ , -C ₁ -C ₆ -(halo) )Alkyl-C(=O)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-C(=O)OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-C( =O)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl -C(=O)N(OR ²¹ )R ²¹ , -C ₁ -C ₆ -(halo)alkyl -C(=O)NR ²¹ N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-C(=S)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo Base) alkyl-N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ C(=O)OR ²¹ , -C ₁ -C ₆ -(halo)alkyl- NR ²¹ C(=O)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl -NR ²¹ C(=O)R ²¹ , -C ₁ -C ₆ -(halo)alkyl Group -NR ²¹ C(=S)R ²¹ , -C ₁ -C ₆ -(halo)alkyl -NR ²¹ C(=S)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo )Alkyl-OC(=O)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-OC(=O)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkane -NR ²¹ S(=O) ₂ R ²¹ , -C ₁ -C ₆ -(halo)alkyl-SR ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O)OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O) ₂ R ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O) ₂ OR ²¹ and -C ₁ -C ₆ -(halo)alkyl-S(=O) ₂ N(R ²¹ ) ₂ , where R ²¹ As described in the text, preferably R ²¹ is independently selected from the group consisting of hydrogen, C ₁ -C ₆ -(halo)alkyl, aryl and -C ₁ -C ₆ -(halo) ) Alkyl-aryl, wherein the acyclic R2 and R ²¹ groups may be substituted by one or more R ^22a substituents and the cyclic R2 and R ²¹ groups may be substituted by one or more R ^22c substituents, R ^22a and R ^22c is as described in the text.

In some specific examples, according to specific examples (Ia), (Ib) and (Ic), R1 is a hydrogen atom.

In some specific examples, according to specific examples (Ia), (Ib) and (Ic), X is hydrogen.

In some specific examples, according to specific examples (Ia), (Ib) and (Ic), X is fluorine.

In some specific examples, according to specific examples (Ia), (Ib) and (Ic), X is chlorine.

In some specific examples, according to specific examples (Ia), (Ib) and (Ic), R1 is a hydrogen atom and X is a chlorine atom.

In some specific examples, according to specific examples (Ia), (Ib) and (Ic), R1 is a hydrogen atom and X is a fluorine atom.

In some specific examples, n is 1 according to specific examples (Ia), (Ib), and (Ic).

In some specific examples, according to specific examples (Ia), (Ib) and (Ic), n is 1 and m is 0.

In some specific examples, according to specific examples (Ia), (Ib) and (Ic), R2 is independently selected from the group consisting of halogen, cyano, C ₁ -C ₆ -alkyl (such as methyl Group, ethyl, propyl, isopropyl, butyl, isobutyl), C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylamino (E.g. methylamino), di-C ₁ -C ₆ -alkylamino, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ -haloalkynyl, C ₁ -C ₆ -alkylsulfanyl, C ₃ -C ₁₀ -carbocyclyl, aryl (e.g. phenyl), heteroaryl, -C(=O)R ²¹ , -C(=O)OR ²¹ , -N(R ²¹ ) ₂ , -OC ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl- C ₃ -C ₁₀ -carbocyclyl, -C ₁ -C ₆ -(halo)alkyl-3-to 10-membered-heterocyclyl, -C ₁ -C ₆ -(halo)alkyl-aryl Group, -C ₁ -C ₆ -(halo)alkyl-heteroaryl, -C ₁ -C ₆ -(halo)alkyl-OR ²¹ and -C ₁ -C ₆ -(halo)alkyl -C(=O)OR ²¹ , wherein R ²¹ is as described in the text, preferably R ²¹ is independently selected from the group consisting of hydrogen, C ₁ -C ₆ -(halo)alkyl, aryl And -C ₁ -C ₆ -(halo)alkyl-aryl. The acyclic or cyclic R2 and R ²¹ groups may be substituted as described herein, preferably by halogen or C ₁ -C ₆ -(halo)alkyl.

In some specific examples, according to specific examples (Ib) and (Ic), it is excluded that R1 is hydrogen, X is F, Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if any exists) ) Is a compound of methyl or ethyl.

In some specific examples, according to specific examples (Ib) and (Ic), it is excluded that R1 is hydrogen, X is F, Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if any ) Is a C ₁ -C ₆ -alkyl compound.

In some specific examples, according to specific examples (Ib) and (Ic), Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if any) is C ₁ -C _6- Alkyl compounds.

In some specific examples, according to specific examples (Ib) and (Ic), it is excluded that Het is pyrazolyl or oxadiazolyl, n is 0 or 1, and R2 (if present) is C ₁ -C ₆ -Alkyl compounds.

In some specific examples, according to specific examples (Ib) and (Ic), n is 1 or 2, and R2 is independently selected from the group consisting of halogen, cyano, C ₁ -C ₆ -haloalkane Group, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -Alkynyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ -haloalkynyl, C ₁ -C ₆ -alkylsulfanyl, C ₃ -C ₁₀ -carbocyclyl, aryl, hetero Aryl, -C(=O)R ²¹ , -C(=O)OR ²¹ , -N(R ²¹ ) ₂ , -OC ₁ -C ₆ -(halo)alkyl-aryl, -C _1- C ₆ -(halo)alkyl-C ₃ -C ₁₀ -carbocyclyl, -C ₁ -C ₆ -(halo)alkyl-3- to 10-membered-heterocyclyl, -C ₁ -C ₆ -(Halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl-heteroaryl, -C ₁ -C ₆ -(halo)alkyl-OR ²¹ and -C ₁ -C ₆ -(halo)alkyl-C(=0)OR ²¹ , wherein R ²¹ is as described in the text and the acyclic or cyclic R2 and R ²¹ groups can be substituted as described in the text. Preferably, R ²¹ is independently selected from the group consisting of hydrogen, C ₁ -C ₆ -(halo)alkyl, aryl, and -C ₁ -C ₆ -(halo)alkyl-aryl The group, and the groups R ² and R ²¹ may be substituted with halogen or C ₁ -C ₆ -(halo)alkyl.

其中 R1  係選自由下列組成之群組：氫、C₁ -C₆ -烷基和–C(=O)R^a ，其中R^a 為C₁ -C₆ -烷基(例如甲基)，較佳地R1為氫； m    為0或1； Het 係選自由下列組成之群組：呋喃基、噻吩基、吡咯基、異㗁唑基、異噻唑基、吡唑基、㗁唑基、噻唑基、咪唑基、㗁二唑基、噻二唑基、三唑基和四唑基； X    為氫、氟或氯原子，較佳地氟； n     為0、1或2； R2  係獨立地選自由下列組成之群組：鹵素、氰基、C₁ -C₆ -烷基、C₁ -C₆ -鹵烷基、C₁ -C₆ -烷氧基、C₁ -C₆ -烷基胺基、二-C₁ -C₆ -烷基胺基、C₁ -C₆ -烯基、C₂ -C₆ -炔基、C₂ -C₆ -鹵烯基、C₂ -C₆ -鹵炔基、C₁ -C₆ -烷基氫硫基、C₃ -C₁₀ -碳環基 (較佳地C₃ -C₆ -碳環基)、芳基(例如苯基)、雜芳基 (較佳地包括一或二個雜原子之5或6-員雜芳基，例如噻吩基、吡啶基)、-C(=O)R²¹ 、-C(=O)OR²¹ 、-N(R²¹ )₂ 、-O-C₁ -C₆ -(鹵基)烷基-芳基、-C₁ -C₆ -(鹵基)烷基-C₃ -C₁₀ -碳環基、-C₁ -C₆ -(鹵基)烷基-3-至10-員-雜環基、-C₁ -C₆ -(鹵基)烷基-芳基、-C₁ -C₆ -(鹵基)烷基-雜芳基、-C₁ -C₆ -(鹵基)烷基-OR²¹ 和-C₁ -C₆ -(鹵基)烷基-C(=O)OR²¹ ，其中R²¹ 係如文中所述；較佳地R²¹ 係獨立地選自由下列組成之群組：氫、C₁ -C₆ -(鹵基)烷基、芳基和-C₁ -C₆ -(鹵基)烷基-芳基，且非環狀或環狀R2和R²¹ 基可如文中所述經取代，較佳地經鹵素或C₁ -C₆ -(鹵基)烷基取代。In some specific examples (the text refers to the specific example Id), the compound of the present invention is a compound of formula (I)

Wherein R1 is selected from the group consisting of the group consisting of: hydrogen, C ₁ -C ₆ - alkyl and -C (= O) R ^a, wherein R ^a is C ₁ -C ₆ - alkyl (e.g. methyl), more Preferably R1 is hydrogen; m is 0 or 1; Het is selected from the group consisting of furyl, thienyl, pyrrolyl, isoazolyl, isothiazolyl, pyrazolyl, azolyl, thiazolyl , Imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl and tetrazolyl; X is hydrogen, fluorine or chlorine atom, preferably fluorine; n is 0, 1 or 2; R2 is independently selected from The group consisting of: halogen, cyano, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylamino , Di-C ₁ -C ₆ -alkylamino, C ₁ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ -haloalkynes Group, C ₁ -C ₆ -alkylsulfanyl, C ₃ -C ₁₀ -carbocyclyl (preferably C ₃ -C ₆ -carbocyclyl), aryl (e.g. phenyl), heteroaryl ( Preferably, a 5- or 6-membered heteroaryl group containing one or two heteroatoms, such as thienyl, pyridyl), -C(=O)R ²¹ , -C(=O)OR ²¹ , -N(R ²¹ ) ₂ , -OC ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl -C ₃ -C ₁₀ -carbocyclic group, -C ₁ -C ₆ -(Halo)alkyl-3- to 10-membered-heterocyclyl, -C ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl -Heteroaryl, -C ₁ -C ₆ -(halo)alkyl-OR ²¹ and -C ₁ -C ₆ -(halo)alkyl-C(=O)OR ²¹ , wherein R ²¹ is as in the text Said; preferably R ²¹ is independently selected from the group consisting of hydrogen, C ₁ -C _6- (halo) alkyl, aryl and -C ₁ -C _6- (halo) alkyl -Aryl, and the acyclic or cyclic R2 and R ²¹ groups may be substituted as described herein, preferably by halogen or C ₁ -C ₆ -(halo)alkyl.

In some specific examples, according to specific examples (Id), R2 is independently selected from the group consisting of fluorine, chlorine, cyano, methyl, ethyl, propyl, isopropyl, butyl, isopropyl Butyl, trifluoromethyl, difluoromethyl, methoxy, allyl, cyclopropyl, cyclopentyl, phenyl, thienyl, pyridyl, -C(=O)H, methylcarbonyl, tert-butoxy carbonyl group, -CH ₂ - cyclopropyl, -CH ₂ - (N-morpholinyl it fu), - CH ₂ - phenyl (benzyl), - CH ₂ - thienyl, -CH ₂ -Pyridyl, methoxyethyl, -CH ₂ -C(=O)OH, -CH ₂ -C(=O)O-methyl and -CH ₂ -C(=O)O-ethyl, where Acyclic and cyclic R2 groups can be substituted by halogen or C ₁ -C ₆ -(halo)alkyl. In particular, the phenyl group may be substituted with halogen, such as fluorine or chlorine.

In some specific examples, according to the specific example (Id), it is excluded that R1 is hydrogen, X is F, Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present) is methyl Or ethyl compounds.

In some specific examples, according to the specific example (Id), it is excluded that R1 is hydrogen, X is F, Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present) is C _1- C ₆ -alkyl compounds.

In some specific examples, according to specific example (Id), compounds in which Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if any) is C ₁ -C ₆ -alkyl are excluded .

In some specific examples, according to the specific example (Id), it is excluded that Het is pyrazolyl or oxadiazolyl, n is 0 or 1, and R2 (if any) is a C ₁ -C ₆ -alkyl group. Compound.

In some specific examples, according to the specific example (Id), n is 1, 2, 3, or 4, preferably 1 or 2, and R2 is independently selected from the group consisting of: halogen, cyano, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₂ -C ₆ -alkene Group, C ₂ -C ₆ -alkynyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ -haloalkynyl, C ₁ -C ₆ -alkylsulfanyl, C ₃ -C ₁₀ -carbon Cyclic, aryl, heteroaryl, -C(=O)R ²¹ , -C(=O)OR ²¹ , -N(R ²¹ ) ₂ , -OC ₁ -C ₆ -(halo)alkyl- Aryl, -C ₁ -C ₆ -(halo)alkyl-C ₃ -C ₁₀ -carbocyclyl, -C ₁ -C ₆ -(halo)alkyl-3-to 10-membered-heterocycle Group, -C ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl-heteroaryl, -C ₁ -C ₆ -(halo)alkyl -OR ²¹ and -C ₁ -C ₆ -(halo)alkyl-C(=O)OR ²¹ , wherein R ²¹ is as described in the text and wherein acyclic or cyclic R 2 and R ²¹ groups can be as requested Substitution described in item 1. Preferably, R ²¹ is independently selected from the group consisting of hydrogen, C ₁ -C ₆ -(halo)alkyl, aryl, and -C ₁ -C ₆ -(halo)alkyl-aryl The groups and R ² and R ²¹ groups may be substituted by halogen or C ₁ -C ₆ -(halo)alkyl.

In some specific examples, according to specific examples (Id), n is 1, 2, 3, or 4, preferably 1 or 2, and R2 is independently selected from the group consisting of: fluorine, chlorine, cyano, propyl Base, isopropyl, butyl, isobutyl, trifluoromethyl, difluoromethyl, methoxy, allyl, cyclopropyl, cyclopentyl, phenyl, thienyl, pyridyl, -C (=O)H, methylcarbonyl, tertiary butoxycarbonyl, -CH ₂ -cyclopropyl, -CH ₂ -(N-morpholinyl), -CH ₂ -phenyl (benzyl), -CH ₂ -Thienyl, -CH ₂ -pyridyl, methoxyethyl, -CH ₂ -C(=O)OH, -CH ₂ -C(=O)O-methyl and -CH ₂ -C (=O) O-ethyl, wherein the acyclic and cyclic R2 groups can be substituted by halogen or C ₁ -C ₆ -(halo)alkyl. In particular, the phenyl group may be substituted with halogen, such as fluorine or chlorine.

In some specific examples, according to specific examples (Ia), (Ib), (Ic) and (Id), Het is selected from the group consisting of pyrazolyl, isothiazolyl and ethadiazolyl.

In some specific examples, according to specific examples (Ia), (Ib), (Ic) and (Id), R2 is independently selected from the group consisting of _{C 1} -C _{6 -haloalkyl, such as trifluoromethyl}基 and difluoromethyl.

The present invention also relates to any compound of formula (I) disclosed in Table 1.

The present invention relates to compounds of formula (I) selected from the group consisting of: 2-[4-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]pyrazol-1-yl] ethyl acetate, 1-[5-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]thiophen-2-yl]ethanone, 3-(4-thiophen-3-ylphenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[1-(4-Fluorophenyl)pyrazol-4-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-[Chloro(difluoro)methyl]-3-[4-(1-ethylpyrazol-4-yl)phenyl]-4H-1,2-oxazol-5-ol, 3-[4-(4-Methylthiophen-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[1-(2-methylpropyl)pyrazol-4-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(4-phenyl-1,3-thiazol-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-(4-Thien-2-ylphenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(1-methylpyrrol-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[1-(Difluoromethyl)pyrazol-4-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-(Trifluoromethyl)-3-[4-(1,3,5-trimethylpyrazol-4-yl)phenyl]-4H-1,2-oxazol-5-ol, 3-[4-(1-Prop-2-ylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(5-phenylthiophen-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]thiophene-2-carbaldehyde, 3-[4-[1-methyl-3-(trifluoromethyl)pyrazol-4-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazole-5- alcohol, 3-[4-(1-ethylpyrazol-4-yl)-3-fluorophenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[5-(morpholin-4-ylmethyl)thiophen-2-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol , 3-[4-(3-methoxythiophen-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(5-Propan-2-yl-1,3-thiazol-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(furan-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[2-Fluoro-4-(1-methylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-[Chloro(difluoro)methyl]-3-[4-(1,2-oxazol-4-yl)phenyl]-4H-1,2-oxazol-5-ol, 3-[4-(1-Benzylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[1-(2-Methoxyethyl)pyrazol-4-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, [3-[4-(1-ethylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-yl]acetate, 3-[4-(1-propylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 2-[4-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]pyrazol-1-yl]acetic acid, 3-[4-(5-methylfuran-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-[Chloro(difluoro)methyl]-3-[4-(1-methylpyrazol-4-yl)phenyl]-4H-1,2-oxazol-5-ol, 4-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]pyrazole-1-carboxylic acid tert-butyl ester, 3-[4-(1,3-dimethylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(1-cyclopentylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-(4-imidazol-1-ylphenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(1-phenylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[1-(Thien-2-ylmethyl)pyrazol-4-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(3-Methyl-1,2-oxazol-5-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(1-ethyltriazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[2-Fluoro-4-(1,2-oxazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, [3-[4-(1-Ethylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-yl]2-methoxyethyl Acid ester, [3-[4-(1-ethylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-yl]acetate, 3-[4-(1-ethylpyrazol-4-yl)-2-fluorophenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(2-Chlorothiophen-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]thiophene-2-carbonitrile, 3-[4-(1-methylpyrrol-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazole-5- alcohol, 3-[4-[5-(2,4-Difluorophenyl)-1,2,4-oxadiazol-3-yl]phenyl]-5-(trifluoromethyl)-4H-1, 2-oxazol-5-ol, 3-[4-[5-(2,4-Difluorophenyl)-1,3,4-oxadiazol-2-yl]phenyl]-5-(trifluoromethyl)-4H-1, 2-oxazol-5-ol, 3-[4-[5-(Difluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazole -5-ol, 3-[4-(5-cyclopentyl-1,3,4-oxadiazol-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazole-5- alcohol, 3-[4-(5-Methyl-1,2,4-oxadiazol-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol , 3-[4-[5-(2-chlorophenyl)-1,3,4-㗁diazol-2-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-㗁Azol-5-ol, 3-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol , 3-[4-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazole -5-ol, 3-[4-(5-tert-butyl-1,3,4-thiadiazol-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazole-5 -alcohol, 3-[4-(1-tert-butylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(3-prop-2-enylimidazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-(Trifluoromethyl)-3-[4-[5-(Trifluoromethyl)-1,3,4-diazol-2-yl]phenyl]-4H-1,2-oxazole -5-ol, 5-(Trifluoromethyl)-3-[4-[5-(Trifluoromethyl)-1,2,4-diazol-3-yl]phenyl]-4H-1,2-oxazole -5-ol, 3-[4-(1-pyridin-2-ylpyrazol-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]thiophene-2-carbaldehyde, 4-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]thiophene-2-carbaldehyde, 5-methyl-3-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]thiophene-2-carbaldehyde, 3-[4-(3-Methyl-1,2,4-oxadiazol-5-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol , 3-[4-(5-tert-butyl-1,3,4-oxadiazol-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazole-5 -alcohol, 3-[4-(1,3-thiazol-5-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(1,2-thiazol-5-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(1,2-thiazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazole-5- alcohol, 3-[4-[1-(Cyclopropylmethyl)pyrazol-4-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol and 3-[4-(1-Cyclopropylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol.

According to the present invention, the compounds of formula (I) can be used as fungicides (that is, for controlling phytopathogenic fungi, especially fungi that cause rust or Oomycte in plant protection). Method for preparing compound of formula I

The compound of formula (I) can be prepared according to the methods described in WO2008/006561 and WO2019/122393.

The following table lists the abbreviations used in this paragraph and the example chapters that are not explained in the text. abbreviation significance Ac Acetyl AIBN α,α'-Azobisisobutyronitrile Boc Tertiary butoxycarbonyl c- ring- CI Chemical ionization DCM Dichloromethane DIPEA N,N-Diisopropylethylamine DMAP N,N-Dimethylaminopyridine DMF N,N-Dimethylformamide DMSO Dimethyl sulfoxide EDCI 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride eq. equivalent ESI Electrospray ionization h hour HATU O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethylurea hexafluorophosphate HPLC High performance liquid chromatography LC-MS Liquid Chromatography Mass Spectrometry MS Mass spectrometry NMR Nuclear Magnetic Resonance: Chemical shift (δ) expressed in ppm OTf Trifluoromethylsulfonyl- PG Protecting group ppm millionth Rf Backflow rt or rt Room temperature T3P 1-Propylphosphonic acid cyclic anhydride TEA Triethylamine TFA Trifluoroacetate THF Tetrahydrofuran

I‘                                                     I‘-I通式 I 化合物之通用合成路徑 It is understood that when in an aqueous vehicle, wherein R1 is hydrogen and R2, X, m, n and Het are as defined above, the compound of formula (I') can be combined with the corresponding ring-opened form (ie formula (I'- I) The compound) exists in a reversible equilibrium.

I'I'-I General synthesis route for compounds of general formula I

The present invention also relates to methods for preparing compounds of formula (I). Unless otherwise indicated, the X, R1, R2, m, n and Het groups have the meanings given by the compound of formula (I) above. These definitions apply not only to the final product of formula (I) but also to all intermediates.

方法P1The compound of formula (I') in which R1=H can be prepared according to method P1 by combining the diketone of formula (II) with hydroxylamine (or its hydrochloride) in the presence of a base such as sodium hydroxide or sodium acetate, React in water and/or a solvent, such as ethanol (as described in J. Org. Chem., 1995, 60, 3907-3909) or in the presence of an acid, such as acetic acid, optionally in a solvent such as ethanol (As described, for example, in Journal of Heterocyclic Chemistry, 2010, 47(6), 1310-1316).

Method P1

方法P2The diketone of formula (II) can be processed according to known processes (see, for example, WO2008006561), as shown in method P2, by treating the ketone of formula (III) with a suitable base, preferably in a solvent (for example, ethanol Sodium in ethanol or sodium hydride in THF), followed by the addition of a fluoroacetyl electrophile, such as ethyl trifluoroacetate, to prepare.

Method P2

It can be understood that X, R2, m, n and Het are as defined above according to the present invention. The intermediate of formula (II) can be diketone (as shown in methods P1 and P2) or in the form of ketoenol or a combination of two forms. The mixture exists. Two forms or a mixture of two forms are suitable for method P2.

The compound of formula (III) can be commercially available or can be prepared from readily available compounds according to known processes.

方法P3The compound of formula (I) can be prepared according to method P3 by combining the compound of formula (I') in which R1=H and the electrophile of formula (IV) in which LG1 is a leaving group, such as chlorine, in a suitable base. For example, in the presence of triethylamine, it is prepared by reacting in a suitable solvent, such as, for example, DCM or THF (see, for example, Journal of Heterocyclic Chemistry, 2005, 42(7), 1253-1255).

Method P3

The compound of formula (IV) is commercially available or can be prepared from readily available compounds according to known processes.

方法P4Alternatively, the compound of formula (I) can be used according to method P4, from the compound of formula (V) in which W1 is a leaving group, such as bromine, by combining with the compound of formula (V) in which M1 is a metal or metalloid (such as -B(OH) 2 or -ZnCl) compound of formula (VI), in the presence of a base (e.g. cesium carbonate) and a catalyst (e.g., tetrakis (triphenylphosphine) palladium (0)), in a solvent, such as dioxane and water The coupling reaction is prepared.

Method P4

The compound of formula (V) can be purchased on the market or can be prepared from easily available compounds in a similar way to methods P1 and P2.

The compound of formula (VI) can be commercially available or can be prepared from readily available compounds according to known processes. Alternatively, the compound of formula (VI) can be produced in situ from the corresponding halo derivative by halogen-metal exchange before the coupling reaction.

方法P5Alternatively, the compound of formula (I) can be selected from the compound of formula (VII) in which M2 is a metal or metalloid (for example -B(OH)2 or -ZnCl) according to method P5, by and W2 is one Leaving groups, such as bromine compounds of formula (VIII), in the presence of a base (e.g. cesium carbonate) and a catalyst (e.g., tetrakis(triphenylphosphine)palladium(0)) in the presence of a solvent, such as diethylene and Coupling reaction in water to be prepared.

Method P5

The compound of formula (VIII) is commercially available or can be prepared from readily available compounds according to known processes.

方法P6The compound of formula (VII) can be prepared according to method P6 from the compound of formula (V) in which W1 is a leaving group, such as bromine, by halogen metal exchange or by palladium-catalyzed boronylation. Methods P6 and P5 can be combined in a one-pot method.

Method P6

According to the present invention, the methods P1 to P6 can be carried out if appropriate in the presence of a solvent and if appropriate in the presence of a base.

Suitable solvents for carrying out the methods P1 to P6 according to the invention are conventional inert organic solvents. The preferred system uses halogenated aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or ten Hydronaphthalene; chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, isopropyl ether, methyl tert-butyl ether, methyl 3-pentyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; nitriles, such as acetonitrile, propionitrile, n- Or isobutyronitrile or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformaniline, N-methylpyrrolidone Or hexamethylphosphoramide; esters, such as methyl acetate or ethyl acetate, sulfite, such as dimethyl sulfite, or sulfite, such as cyclobutane.

Suitable bases for carrying out the methods P1 to P6 according to the invention are the inorganic and organic bases customarily used for these reactions. Preferably, alkaline earth metals, alkali metal hydrides, alkali metal hydroxides or alkali metal alcoholates are used, such as sodium hydroxide, sodium hydride, calcium hydroxide, potassium hydroxide, potassium tert-butoxide or other ammonium hydroxides , Alkali metal carbonates, such as sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, cesium carbonate, alkali metal or alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetate and tertiary amines, such as trimethylamine , Triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, pyridine, N-methylpiperidine, N,N-dimethylaminopyridine, 1,4- Diazabicyclo[2.2.2]octane (DABCO), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), or 1,8-diazabicyclo[5.4.0] Undec-7-ene (DBU).

When performing methods P1 to P6, according to the present invention, the reaction temperature can independently be varied within a fairly wide range. Generally speaking, the method according to the invention is carried out at a temperature between -20°C and 160°C.

The methods P1 to P6 according to the present invention are generally carried out independently under atmospheric pressure. However, it is also possible to operate under elevated or reduced pressure.

The subsequent processing is carried out by conventional methods. Generally, the reaction mixture is treated with water to separate the organic phase and, after drying, it is concentrated under reduced pressure. If appropriate, the remaining residue can be released from impurities that may still be present by conventional methods, such as chromatography or recrystallization.

The compounds according to the present invention can be prepared according to the methods described above. However, it should be understood that those skilled in the art, based on their general knowledge or available publications, should be able to adjust these methods according to the details of each compound of the present invention to be synthesized.

Refer to the following examples to further understand the state of this teaching, which should not be construed as limiting the scope of this teaching in any way. Composition and formulation

The present invention further relates to a composition comprising one or more compounds of formula (I), especially a composition for controlling unwanted microorganisms. The composition is preferably a fungicidal composition.

The composition typically includes one or more compounds of formula (I) and one or more acceptable carriers, especially one or more agriculturally acceptable carriers.

The carrier is a solid or liquid, natural or synthetic, organic or inorganic substance, which is generally inert. The carrier generally promotes the application of the compound, such as plants, plant parts, or seeds. Examples of suitable solid carriers include, but are not limited to, ammonium salts, natural mineral powders such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth, and synthetic mineral powders For example, fine powdered silica, alumina, and silicate. Examples of useful solid carriers typically used to prepare particles include, but are not limited to, crushed and classified natural ores such as calcite, marble, pumice, sepiolite and dolomite, synthetic inorganic and organic powder particles, and organic substances, For example, particles of paper, sawdust, coconut husks, corn cobs and tobacco stems. Examples of suitable liquid carriers include, but are not limited to, water, organic solvents and combinations thereof. Examples of suitable solvents include polar and non-polar organic chemical liquids, such as from aromatic and non-aromatic hydrocarbons (such as cyclohexane, paraffin, alkylbenzene, xylene, toluene, alkylnaphthalene, chlorinated aromatics and chlorine Aliphatic hydrocarbons, such as chlorobenzene, vinyl chloride or dichloromethane), alcohols and polyols (which can be substituted, etherified and/or esterified as needed, such as butanol or glycol), ketones (E.g. acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), esters (including lipids and oils) and (poly) ethers, unsubstituted and substituted amines, acetone Amines (e.g. dimethylformamide), lactones (e.g. N-alkylpyrrolidone) and lactones, sulfinium and sulfinium (e.g. dimethylsulfinium). The carrier may also be a liquefied gaseous extender, that is, a gaseous liquid at standard temperature and standard pressure, for example, aerosol propellants such as halogenated hydrocarbons, butane, propane, nitrogen, and carbon dioxide. The amount of the carrier, based on the weight of the composition, typically ranges from 1 to 99.99%, preferably from 5 to 99.9%, more preferably from 10 to 99.5%, and most preferably from 20 to 99%.

The composition may further include one or more acceptable adjuvants conventionally used to formulate a composition (such as an agrochemical composition), such as one or more surfactants.

Surfactants can be ionic (cationic or anionic) or nonionic surfactants, such as ionic or nonionic emulsifiers, foam formers, dispersants, wetting agents, and any mixtures thereof. Examples of suitable surfactants include, but are not limited to, polyacrylic acid salts, lignosulfonic acid salts, phenolsulfonic acid or naphthalenesulfonic acid salts, ethylene oxide and/or propylene oxide and fatty alcohols, fatty acids Or polycondensates of fatty amines (polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, such as alkyl aryl polyglycol ethers), substituted phenols (preferably alkyl phenols or aryl phenols) , Salts of sulfosuccinates, taurine derivatives (preferably alkyl taurates), polyethoxylated alcohols or phenolic phosphate esters, fatty acid esters of polyhydric alcohols and sulfuric acid esters Derivatives of sulfonate and phosphate compounds (such as alkyl sulfonate, alkyl sulfate, aryl sulfonate) and protein hydrolysate, lignin sulfite waste liquid and methyl cellulose. When the compound of formula (I) and/or the carrier is insoluble in water and is applied in water, a surfactant is typically used. However, the amount of surfactant, based on the weight of the composition, typically ranges from 5 to 40%.

Further examples of auxiliaries customarily used to formulate agrochemical compositions include waterproofing agents, desiccants, adhesives (adhesives, tackifiers, fixatives, such as carboxymethyl cellulose, natural and natural in the form of powder, granules or latex). Synthetic polymers, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids, such as cephalin and lecithin, and synthetic phospholipids, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, and Taylor gum ( tylose)), thickeners, stabilizers (such as cold stabilizers, preservatives, antioxidants, light stabilizers or other agents that enhance chemical and/or physical stability), dyes or pigments (such as inorganic pigments, such as oxidation Iron, titanium oxide and Prussian blue; organic dyes, such as alizarin, azo and metal phthalocyanine dyes), defoamers (for example, silicone defoamers and magnesium stearate), anti-corrosion Agents (such as dichlorophenol and benzyl alcohol hemiformal), secondary thickeners (cellulose derivatives, acrylic acid derivatives, xanthan gum, modified clay and fine powdered silica), adhesives (stickers), Gibberellins and processing aids, mineral and vegetable oils, fragrances, waxes, nutrients (including micronutrients such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salts), protective colloids, thixotropy Substances, penetrants, sequestering agents and complexing agents.

The choice of adjuvant is related to the desired mode of administration and/or physical properties of the compound of formula (I). Furthermore, the adjuvant may be selected to impart specific properties (technical, physical and/or biological properties) to the composition or the use form prepared therefrom. The choice of additives can be tailored to the specific needs of the composition.

The composition can be in any conventional form, such as solutions (e.g., aqueous solutions), emulsions, wettable powders, water-based and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, granules for cloth application Agents, concentrated suspension emulsions, natural or synthetic products injected with the compounds of the present invention, fertilizers and microencapsulation in polymers. The compound of formula (I) may exist in suspended, emulsified or dissolved form.

The composition can be provided to the end user as a ready-to-use formulation, that is, the composition can be directly applied to plants or seeds by a suitable device, such as a spraying or dusting device. Alternatively, the composition may be provided to the end user in the form of a concentrate, which must be diluted before use, preferably with water.

The composition can be prepared by conventional methods, for example, by mixing the compound of formula (I) with one or more suitable auxiliary agents such as those disclosed above.

The composition generally contains 0.01 to 99% by weight, 0.05 to 98% by weight, preferably 0.1 to 95% by weight, more preferably 0.5 to 90% by weight, and most preferably 1 to 80% by weight. (I) Compound.

Compounds and compositions including them can be combined with other active ingredients, such as fungicides, bactericides, acaricides, nematicides, insecticides, herbicides, fertilizers, growth regulators, safeners or information compounds mixing. This can expand the spectrum of activity or prevent the occurrence of drug resistance. Examples of known fungicides, insecticides, acaricides, nematicides, and bactericides are disclosed in the 17th edition of the Pesticide Manual.

Examples of fungicides that can be mixed with the compound of formula (I) and the composition of the present invention are:

1) Ergosterol biosynthesis inhibitors, such as (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenhexamid ), (1.005) fenpropidin, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009) fenpropimorph (flutriafol), (1.010) imazalil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) Mike Myclobutanil, (1.015) paclobutrazol, (1.016) prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019) chlorhexidine (pyrisoxazole), (1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetraconazole, (1.023) triadimenol, (1.024) tridecamorpholine ( tridemorph), (1.025) triticonazole, (1.026) (1R, 2S, 5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-( 1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.027)(1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl) -2-Methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.028)(2R)-2-(1-chlorocyclopropyl)-4- [(1R)-2,2-Dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol、(1.029)(2R)-2-( 1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.030)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl)-1-(1H-1,2,4-triazol-1-yl )Propan-2-ol, (1.031)(2S)-2- (1-Chlorocyclopropyl)-4-((1R)-2,2-dichlorocyclopropyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol , (1.032)(2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazole -1-yl)butan-2-ol, (1.033)(2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl)-1-(1H-1 ,2,4-Triazol-1-yl)propan-2-ol, (1.034)(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorobenzene) Yl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.035)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2, 4-Difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.036) [3-(4-chloro-2-fluorophenyl)-5-(2 ,4-Difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.037) 1-({(2R,4S)-2-[2-chloro-4 -(4-Chlorophenoxy)phenyl)-4-methyl-1,3-dioxolane-2-yl)methyl)-1H-1,2,4-triazole, (1.038) 1 -({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl }Methyl)-1H-1,2,4-triazole, (1.039) 1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)ethylene oxide ( oxiran)-2-yl]methyl)-1H-1,2,4-triazol-5-yl thiocyanate, (1.040) 1-{[rel(2R,3R)-3-(2-chloro Phenyl)-2-(2,4-difluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazol-5-ylthiocyanate, (1.041 ) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl) oxirane-2-yl]methyl)-1H-1 ,2,4-Triazol-5-yl thiocyanate, (1.042) 2-[(2R,4R,5R)-1-(2,4-Dichlorophenyl)-5-hydroxy-2,6 ,6-Trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.043) 2-[(2R,4R,5S)- 1-(2,4-Dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl)-2,4-dihydro-3H-1,2,4-triazole -3-thioketone, (1.044) 2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhepta-4- Base)-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.0 45) 2-[(2R,4S,5S)-1-(2,4-Dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4- Dihydro-3H-1,2,4-triazole-3-thione, (1.046) 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy- 2,6,6-Trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.047) 2-[(2S,4R, 5S)-1-(2,4-Dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl)-2,4-dihydro-3H-1,2,4 -Triazole-3-thione, (1.048) 2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptane -4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.049) 2-[(2S,4S,5S)-1-(2,4- Dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione, ( 1.050) 2-[1-(2,4-Dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2 ,4-Triazole-3-thione, (1.051) 2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-tri Azol-1-yl)propan-2-ol, (1.052) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazole- 1-yl)butan-2-ol, (1.053) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl)-1-(1H-1,2,4- Triazol-1-yl)butan-2-ol, (1.054) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl)-1-(1H-1,2 ,4-Triazol-1-yl)pentan-2-ol, (1.055) mefentrifluconazole, (1.056) 2-{[3-(2-chlorophenyl)-2-(2, 4-Difluorophenyl)oxirane-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.057) 2-{[ rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane-2-yl)methyl)-2,4-dihydro-3H -1,2,4-Triazole-3-thione, (1.058) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl) )Ethylene oxide-2-yl)methyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.059) 5-(4-chlorobenzyl) -2-(chloromethyl)-2-methyl-1 -(1H-1,2,4-triazol-1-ylmethyl)cyclopropanol, (1.060) 5-(allyl hydrogensulfanyl)-1-{[3-(2-chlorophenyl) -2-(2,4-Difluorophenyl)oxirane-2-yl)methyl)-1H-1,2,4-triazole, (1.061) 5-(allylsulfanyl) -1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1 ,2,4-Triazole, (1.062) 5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4- Difluorophenyl)oxirane-2-yl]methyl}-1H-1,2,4-triazole, (1.063) N'-(2,5-dimethyl-4-{[3- (1,1,2,2-Tetrafluoroethoxy)phenyl)sulfanyl)phenyl)-N-ethyl-N-formiminomethamide, (1.064) N'-(2, 5-Dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-formiminomethamide , (1.065) N'-(2,5-Dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N- Ethyl-N-formiminoformamide, (1.066) N'-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl )-N-ethyl-N-formiminomethamide, (1.067) N'-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethane (Phenoxy)phenyl)-N-ethyl-N-carboxamide, (1.068) N'-(2,5-dimethyl-4-{3-[ (2,2,2-Trifluoroethyl)sulfanyl)phenoxy)phenyl)-N-ethyl-N-carboxamide, (1.069) N'-(2,5- Dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-carboxamide , (1.070) N'-(2,5-Dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimine Carboxamide, (1.071) N'-(2,5-Dimethyl-4-phenoxyphenyl)-N-ethyl-N-carboxamide, (1.072) N'- (4-{[3-(Difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-formiminomethanamide, (1.073 ) N'-(4-{3-[(Difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-formiminomethyl Amine, (1.074) N'-[5-Bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl- N-formiminomethyl Amide, (1.075) N'-{4-[(4,5-Dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl -N-formiminoformamide, (1.076) N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methyl Pyridin-3-yl}-N-ethyl-N-formiminomethamide, (1.077) N'-{5-bromo-6-[(1S)-1-(3,5-difluorobenzene Yl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-formiminomethanamide, (1.078) N'-{5-bromo-6-[(cis- 4-isopropylcyclohexyl)oxy)-2-methylpyridin-3-yl}-N-ethyl-N-carboxamide, (1.079) N'-{5-bromo-6 -[(Trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-formiminomethamide, (1.080) N'-{ 5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-formiminomethamide, (1.081) ipfentrifluconazole (ipfentrifluconazole), (1.082) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl)-1-(1H-1,2 ,4-Triazol-1-yl)propan-2-ol, (1.083) 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1- (1,2,4-Triazol-1-yl)propan-2-ol, (1.084) 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl ]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.085) 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2- Fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile, (1.086) 4-[[6-[racemic-(2R)-2-(2,4-difluorophenyl) -1,1-Difluoro-2-hydroxy-3-(5-sulfanyl-4H-1,2,4-triazol-1-yl)propyl)-3-pyridyl)oxy)benzonitrile , (1.087) N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)phenyl ]-N-carboxamide, (1.088) N'-{5-bromo-2-methyl-6-[(1-propoxyprop-2-yl)oxy]pyridine-3- )-N-ethyl-N-formiminomethanamide, (1.089) hexaconazole, (1.090) penconazole, (1.091) fenbuconazole and (1.092) 2-[2-Chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazole-1- Base) methyl propionate.

2) Inhibitors of respiratory chain complex I or II, such as (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, ( 2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008) furametpyr, ( 2.009) Isopyrazam (isofetamid), (2.010) isopyrazam (reverse-epimeric mirror isomers 1R, 4S, 9S), (2.011) isopyrazam (retro-epimeric mirror image Isomers 1S, 4R, 9R), (2.012) Yapazhan (reverse-epimeric racemate 1RS, 4SR, 9SR), (2.013) Yapazhan (homo-episomeric racemate 1RS) , 4SR, 9RS and retro-epimeric racemates 1RS, 4SR, 9SR mixture), (2.014) Yapaizhan (homo-epimeric enantiomers 1R, 4S, 9R), (2.015) Paizhan (homo-epimeric enantiomers 1S, 4R, 9S), (2.016) Yapaizhan (homo-epimeric racemates 1RS, 4SR, 9RS), (2.017) penflufen (penflufen), (2.018) penthiopyrad, (2.019) pydiflumetofen, (2.020) pyraziflumid, (2.021) sedaxane, (2.022) 1,3 -Dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.023) 1, 3-Dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.024) 1,3-Dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4 -Formamide, (2.025) 1-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-methyl Amide, (2.026) 2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzyl Amine, (2.027) 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H- Pyrazole-4-carboxamide, (2.028) inpyrfluxam, (2.029) 3-(Difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyridine Azole-4-methoxamide, (2.030) fluindapyr, (2.031) 3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-tri Methyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.032) 3-(difluoromethyl)-N-[ (3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide, (2.033) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl)quinazoline -4-amine, (2.034) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H -Pyrazole-4-carboxamide, (2.035) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro -1-Methyl-1H-pyrazole-4-carboxamide, (2.036) N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5 -Fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.037) N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl Yl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.038)isoflucypram, (2.039) N-((1R,4S)-9-(dichloromethylene)- 1,2,3,4-Tetrahydro-1,4-methylenenaphthalene-5-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.040) N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methylenenaphthalene-5-yl)-3-( Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.041) N-[1-(2,4-dichlorophenyl)-1-methoxyprop-2- Yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.042) N-[2-chloro-6-(trifluoromethyl)benzyl] -N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.043) N-[3-chloro-2-fluoro- 6-(Trifluoromethyl)benzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.044 ) N-[5-Chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole- 4-formamide, (2.045) N-cyclopropyl-3-(difluoromethyl)-5-fluoro -1-Methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide, (2.046) N-cyclopropyl-3-( Difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.047) N-cyclopropyl Base-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, ( 2.048) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-thioamide , (2.049) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-methan Amine, (2.050) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole -4-methylamide, (2.051) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1 -Methyl-1H-pyrazole-4-carboxamide, (2.052) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5 -Fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.053) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzene) Methyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.054) N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)- 3-(Difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.055) N-cyclopropyl-N-(2-cyclopropyl-5-methyl Benzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.056) N-cyclopropyl-N-(2-ring Propylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.057) pyrapropoyne, (2.058 ) N-[racemic-(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide, (2.059) N-[ (1S,2S)-2-(2,4-Dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide.

3) Inhibitors of respiratory chain complex III, such as (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin ), (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) cyazofamid, (3.009) famoxadone), (3.010) fenamidone, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013) kresoxim-methyl, (3.014) Metominostrobin, (3.015) orysastrobin, (3.016) picoxystrobin, (3.017) pyraclostrobin, (3.018) pyrametostrobin, (3.019) pyraoxystrobin, (3.020) trifloxystrobin, (3.021)(2E)-2-{2-[({[(1E)-1-(3-{[(E) -1-Fluoro-2-phenylvinyl]oxy)phenyl)ethylene)amino}oxy)methyl)phenyl)-2-(methoxyimino)-N-methyl Acetamide, (3.022)(2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino) -N,3-Dimethylpent-3-enamide, (3.023)(2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2- Methoxy-N-methylacetamide, (3.024)(2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy- N-methylacetamide, (3.025) fenpicoxamid, (3.026) mandestrobin, (3.027) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3 -Formamido-2-hydroxybenzamide, (3.028)(2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl] Oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.029) methyl {5-[3-(2, 4-Dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate, (3.030) metyltetraprole, (3.031) florylpicoxamid.

4) Inhibitors of mitosis and cell division, such as (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolid , (4.005) pencycuron, (4.006) thiabendazole, (4.007) thiophanate-methyl, (4.008) zoxamide, (4.009) pyridachlometyl, (4.010) ) 3-Chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridine, (4.010) 3-chloro-5-(4-chlorophenyl) )-4-(2,6-Difluorophenyl)-6-methylpyridine, (4.011) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-( 2,4,6-trifluorophenyl) 𠯤, (4.012) 4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl Base-1H-pyrazol-5-amine, (4.013) 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl- 1H-pyrazole-5-amine, (4.014) 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazole-5 -Amine, (4.015) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine , (4.016) 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.017) 4- (2-Bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.018) 4-(2-chloro-4 -Fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.019) 4-(2-chloro-4-fluorobenzene Yl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.020) 4-(2-chloro-4-fluorophenyl) -N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.021) 4-(2-chloro-4-fluorophenyl)-N-(2- Fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.022) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3, 6-Dimethylpyridine, (4.023) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyridine Azol-5-amine, (4.024) N-(2- Bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.025) N-(4-chloro-2,6- Difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.026) fluopimomide.

5) Compounds with multi-site action ability, such as (5.001) Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorthalonil ), (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper sulfate (2+), (5.010) dithianon , (5.011) Dodin, (5.012) Folpet, (5.013) Mancozeb, (5.014) Maneb, (5.015) Metiram , (5.016) to avoid rotten zinc (metiram-zinc), (5.017) oxine copper, (5.018) methyl zinc propineb, (5.019) including sulfur and lime sulfur (calcium polysulfide) Sulfur preparations, (5.020) thiram, (5.021) zineb, (5.022) ziram, (5.023) 6-ethyl-5,7-dioxo-6, 7-Dihydro-5H-pyrrolo[3',4':5,6][1,4]dithieno[2,3-c][1,2]thiazole-3-carbonitrile .

6) Compounds that can trigger host defenses, such as (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) tiadinil.

7) Inhibitors of amino acid and/or protein biosynthesis, such as (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride (kasugamycin) hydrochloride hydrate), (7.004) oxytetracycline, (7.005) pyrimethanil, (7.006) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4- Dihydroisoquinolin-1-yl)quinoline.

8) Inhibitors of ATP production, such as (8.001) silthiofam.

9) Inhibitors of cell wall synthesis, such as (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb , (9.005) mandipropamid, (9.006) pyrimorph, (9.007) valifenalate, (9.008) (2E)-3-(4-tertiary butylphenyl) -3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (9.009)(2Z)-3-(4-tert Phenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

10) Inhibitors of lipid and membrane synthesis, such as (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl.

11) Inhibitors of melanin biosynthesis, such as (11.001) tricyclazole, (11.002) tolprocarb.

12) Nucleic acid synthesis inhibitors, such as (12.001) Benalaxyl, (12.002) Benalaxyl-M (kiralaxyl), (12.003) Metalaxyl, (12.004) dexmeda Le (metalaxyl-M) (mefenoxam).

13) Inhibitors of signal transduction, such as (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, ( 13.005) Quinoxyfen, (13.006) Vinclozolin.

14) Compounds that can act as decoupling agents, such as (14.001) fluazinam, (14.002) meptyldinocap.

15) Other fungicides selected from the group consisting of: (15.001) abscisic acid, (15.002) benthiazole, (15.003) bethoxazin, (15.004) capsimycin, (15.005) carvone, (15.006) chinomethionat, (15.007) cufraneb, (15.008) cyflufenamid, (15.009) cymoxanil, ( 15.010) cyprosulfamide (cyprosulfamide), (15.011) flutianil, (15.012) fosetyl-aluminium, (15.013) fosetyl-calcium, (15.014) fosetyl -Fosetyl-sodium, (15.015) methyl isothiocyanate, (15.016) metrafenon, (15.017) mildomycin, (15.018) natamycin (natamycin), (15.019) nickel dimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021) oxamocarb, (15.022) oxathiapiprolin, (15.023) oxyfenthiin, (15.024) pentachlorophenol and its salts, (15.025) phosphorous acid and its salts, (15.026) propamocarb-fosetylate, (15.027) pyriofenone (chlazafenone)), (15.028) tebufloquin, (15.029) tecloftalam, (15.030) tolnifanide, (15.031) 1-(4-(4- [(5R)-5-(2,6-Difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine- 1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (15.032) 1-(4-{4-[(5S)- 5-(2,6-Difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazole- 2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (15.033) 2-(6-benzene (Methylpyridin-2-yl)quinazoline, (15.034) dipymetitrone, (15.035) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4- (4-{5-[2-(Pro-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazole -2-yl)piperidin-1-yl)ethanone, (15.036) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4 -{5-[2-Chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3 -Thiazol-2-yl)piperidin-1-yl]ethanone, (15.037) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4- (4-{5-[2-Fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1 ,3-thiazol-2-yl)piperidin-1-yl)ethanone, (15.038) 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl ]Quinazoline, (15.039) 2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetinyl} Piperidin-4-yl)-1,3-thiazol-4-yl)-4,5-dihydro-1,2-oxazol-5-yl)-3-chlorophenyl methanesulfonate, (15.040 ) 2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl) -1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl)-3-chlorophenyl methanesulfonate, (15.041) ipflufenoquin, (15.042) 2 -{2-Fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (15.043) fluoxapiprolin, (15.044) 2-{3- [2-(1-{[3,5-Bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl ]-4,5-Dihydro-1,2-oxazol-5-yl)phenyl methanesulfonate, (15.045) 2-phenylphenol and salts, (15.046) 3-(4,4,5 -Trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.047) quinofumelin, (15.048) 4-amino-5-fluoropyrimidin-2-ol (Tautomeric form: 4-amino-5-fluoropyrimidine-2(1H)-one), (15.049) 4 -Pendant oxygen-4-[(2-phenylethyl)amino]butyric acid, (15.050) 5-amino-1,3,4-thiadiazole-2-thiol, (15.051) 5-chloro -N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfonamide, (15.052) 5-fluoro-2-[(4-fluorobenzyl)oxy] Pyrimidine-4-amine, (15.053) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.054) 9-fluoro-2,2-dimethyl-5 -(Quinolin-3-yl)-2,3-dihydro-1,4-benzoazepine, (15.055)but-3-yn-1-yl{6-[({[(Z)-( 1-Methyl-1H-tetrazol-5-yl)(phenyl)methylene)amino)oxy)methyl)pyridin-2-yl)carbamate, (15.056) (2Z)-3 -Amino-2-cyano-3-phenylethyl acrylate, (15.057) phenanthrene-1-carboxylic acid, (15.058) 3,4,5-trihydroxybenzoic acid propyl ester, (15.059) quinoline- 8-alcohol, (15.060) quinoline-8-alcohol sulfate (2:1), (15.061) {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl) Methylene]amino}oxy)methyl]pyridin-2-yl}carbamic acid tert-butyl ester, (15.062) 5-fluoro-4-imino-3-methyl-1-[(4- Methylphenyl)sulfonyl)-3,4-dihydropyrimidine-2(1H)-one, (15.063) Aminopyrifen, (15.064)(N'-[2-chloro-4-(2-fluorophenoxy) Yl)-5-methylphenyl)-N-ethyl-N-formiminomethamide), (15.065)(N'-(2-chloro-5-methyl-4-phenoxybenzene Yl)-N-ethyl-N-carboxamide), (15.066)(2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy ]-6-fluorophenyl)propan-2-ol), (15.067)(5-bromo-1-(5,6-dimethylpyridin-3-yl)-3,3-dimethyl-3, 4-dihydroisoquinoline), (15.068)(3-(4,4-difluoro-5,5-dimethyl-4,5-dihydrothieno[2,3-c]pyridine-7- Yl)quinoline), (15.069) (1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4 -Dihydroisoquinoline), (15.070) 8-fluoro-3-(5-fluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinolone, (15.071) 8 -Fluoro-3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinolone, (15.072) 3-(4,4-difluoro -3,3-Dimethyl-3,4-dihydroisoquinolin-1-yl)-8-fluoroquinoline, (1 5.073) (N-methyl-N-phenyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide), (15.074) methyl {4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}carbamate, (15.075)(N-{4-[5-(Trifluoro (Methyl)-1,2,4-oxadiazol-3-yl)benzyl)cyclopropylmethamide), (15.076) N-methyl-4-(5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide, (15.077) N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl]benzamide, (15.078) N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl) -1,2,4-oxadiazol-3-yl]benzamide, (15.079) N-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3- Group]Phenyl]Cyclopropanamide, (15.080) N-(2-Fluorophenyl)-4-[5-(Trifluoromethyl)-1,2,4-Diazol-3-yl] Benzamide, (15.081) 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-diazol-3-yl]benzene Yl]acetamide, (15.082) N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl ]Acetamide, (15.083) N-[(E)-N-methoxy-C-methyl-iminoyl]-4-(5-(trifluoromethyl)-1,2,4 -Diazol-3-yl]benzamide, (15.084) N-[(Z)-N-methoxy-C-methyl-iminoyl]-4-[5-(trifluoro Methyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.085) N-allyl-N-[[4-[5-(trifluoromethyl)-1, 2,4-Diazol-3-yl]phenyl]methyl]propanamide, (15.086) 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1 ,2,4-Diazol-3-yl]phenyl]methyl]pyrrolidinyl-2-one, (15.087) N-methyl-4-[5-(trifluoromethyl)-1,2 ,4-Diazol-3-yl]thiobenzamide, (15.088) 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-㗁二Azol-3-yl]phenyl)methyl]pyrrolidinyl-2-one, (15.089) N-((2,3-difluoro-4-[5-(trifluoromethyl)-1,2, 4-Diazol-3-yl]phenyl]methyl]-3,3,3-trifluoro-propanamide, (15.090) 1-methoxy-1-methyl-3-[[4- [5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15. 091) 1,1-Diethyl-3-[[4-[5-(trifluoromethyl)-1,2,4-diazol-3-yl]phenyl]methyl]urea, (15.092 ) N-[[4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.093) N-methoxy- N-[[4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropylcarbamide, (15.094) 1-methoxy -3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.095) N-methyl Oxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl)cyclopropylmethamide, (15.096) N, 2-Dimethoxy-N-[[4-[5-(trifluoromethyl}-1,2,4-㗁diazol-3-yl]phenyl]methyl]propanamide, (15.097) N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl]propanamide, (15.098) 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl)methyl) Urea, (15.099) 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl] Urea, (15.100) 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-diazol-3-yl]phenyl]methane Yl]urea, (15.101) 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.102) 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl)methyl]isoxazole Pyridin-3-one, (15.103) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-diazol-3-yl]phenyl] Methyl]isoazolidine-3-one, (15.104) 3,3-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3 -Yl]phenyl]methyl]piperidin-2-one, (15.105) 1-[[3-fluoro-4-(5-(trifluoromethyl)-1,2,4-diazole-3 -Yl]phenyl]methyl]aza-2-one, (15.106) 4,4-dimethyl-2-[[4-(5-(trifluoromethyl)-1,2,4-㗁Diazol-3-yl]phenyl]methyl]isoazolidine-3-one, (15.107) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1 ,2,4-Diazol-3-yl]phenyl]methyl]isoazolidin-3-one, (15.108) 1-{4-[5-(trifluoromethyl )-1,2,4-Diazol-3-yl]benzyl}-1H-pyrazole-4-carboxylic acid ethyl ester, (15.109) N,N-dimethyl-1-{4-[ 5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl)-1H-1,2,4-triazol-3-amine, (15.110) N-{2 ,3-Difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}butyramide, (15.111) N-(1-methyl) Cyclopropyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.112) N-(2,4-difluorophenyl) )-4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.113) 1-(5,6-dimethylpyridine-3- Yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.114) 1-(6-(difluoromethyl)-5-methyl-pyridine- 3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.115) 1-(5-(fluoromethyl)-6-methyl-pyridine -3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.116) 1-(6-(difluoromethyl)-5-methoxy -Pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.117) 4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl dimethyl carbamate, (15.118) N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazole -3-yl]phenyl}propanamide, (15.119) 3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetamide Yl)piperidin-4-yl)-1,3-thiazol-4-yl)-1,5-dihydro-2,4-benzodioxo-6-yl methanesulfonate, (15.120) 9 -Fluoro-3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1, 3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxo-6-yl methanesulfonate, (15.121) 3-[2-(1-{[3,5 -Bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl)piperidin-4-yl)-1,3-thiazol-4-yl)-1,5-dihydro-2, 4-benzodioxo-6-yl methanesulfonate, (15.122) 3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl] Acetyl)piperidin-4-yl)-1,3-thiazol-4-yl)-9-fluoro-1,5-dihydro-2,4-benzodiox-6-ylmethanesulfonic acid Ester, (15.123) 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl Base-3,4-dihydroisoquinoline, (15.124) 8-fluoro-N-(4,4,4-trifluoro-2-methyl-1-phenylbut-2-yl)quinoline-3 -Formamide, (15.125) 8-fluoro-N-[(2S)-4,4,4-trifluoro-2-methyl-1-phenylbut-2-yl]quinoline-3-methan Amine, (15.126) N-(2,4-dimethyl-1-phenylpent-2-yl)-8-fluoroquinoline-3-carboxamide and (15.127) N-((2S)-2 ,4-Dimethyl-1-phenylpent-2-yl]-8-fluoroquinoline-3-carboxamide.

All of the compounds mentioned above (1) to (15) can be free compounds and/or, if their functional groups are feasible, exist in their agriculturally acceptable salts.

The compound of formula (I) and the composition comprising them can be combined with one or more biological control agents.

Examples of biological control agents that can be combined with compounds of formula (I) and compositions containing them are: (A) An antibacterial agent selected from the following group:

(A1) Bacteria, such as (A1.1) Bacillus subtilis ( Bacillus subtilis ), especially QST713/AQ713 strain (available as SERENADE OPTI or SERENADE ASO, from Bayer CropScience LP, USA, with NRRL accession number B21661 and such as US Patent No. 6,060,051); (A1.2) Liquefied Bacillus amyloliquefaciens (Bacillus amyloliquefaciens), especially the D747 strain (available as Double Nickel™, from Certis, USA, with accession number FERM BP-8234 and (Disclosed in U.S. Patent No. 7,094,592); (A1.3) Bacillus pumilus , especially BU F-33 strain (with NRRL accession number 50185); (A1.4) Liquefied starch Bacillus subtilis variant ( Bacillus subtilis var. amyloliquefaciens ) FZB24 strain (available as Taegro®, from Novozymes, USA); (A1.5) Paenibacillus sp. has accession number NRRL B-50972 or accession number NRRL B-67129 Strains and are described in International Patent Publication No. WO 2016/154297; and

(A2) Fungi, such as (A2.1) Aureobasidium pullulans , especially spores of strain DSM 14940; (A2.2) Aureobasidium pullulans, spores of strain DSM 14941; (A2.3) Aureobasidium pullulans, especially a mixture of spores of strains DSM14940 and DSM14941; (B) A fungicide selected from the following group:

(B1) Bacteria, such as (B1.1) Bacillus subtilis ( Bacillus subtilis ), especially the QST713/AQ713 strain (available as SERENADE OPTI or SERENADE ASO, from Bayer CropScience LP, USA, with NRRL accession number B21661 and such as As described in U.S. Patent No. 6,060,051; (B1.2) Bacillus pumilus, especially the QST2808 strain (available as SONATA®, from Bayer CropScience LP, USA, with accession number NRRL B-30087 and as in U.S. Patent No. 6,245,551 (B1.3) Bacillus pumilus, especially the GB34 strain (Yield Shield® available from Bayer AG, Germany); (B1.4) Bacillus pumilus, especially BU F-33 Strain (with NRRL accession number 50185); (B1.5) Liquefied Bacillus amylolique, especially the D747 strain (available as Double Nickel™, from Certis, USA, with accession number FERM BP-8234 and disclosed in US Patent No. 7,094,592); (B1.6) Bacillus subtilis Y1336 (available as BIOBAC ^® WP, from Taiwan Bion-Tech Company, registered as a biofungicide in Taiwan, registration number 4764, 5454, 5096 and 5277); (B1.7) Liquefied Bacillus amylolus MBI 600 strain (Subtilex, available from BASF SE); (B1.8) Bacillus subtilis GB03 strain (available as Kodiak®, from Bayer AG, Germany); (B1.9) Liquefied starch Bacillus subtilis strain FZB24 (available from Novozymes Biologicals Inc., Salem, Virginia, or Syngenta Crop Protection, LLC, Greensboro, Northern California, as a fungicide TAEGRO ^® Or TAEGRO ^® ECO (EPA registration number 70127-5); (B1.10) Bacillus mycoides isolate J (available as BmJ TGAI or WG, from Certis, USA); (B1.11) Bacillus licheniformis ( Bacillus licheniformis ), especially SB3086 strain (available as EcoGuard TM Biofungicide and Green Releaf, from Novozymes); (B1.12) has the accession number NRRL B-50972 or Bacillus strains like the accession number NRRL B-67129 are described in International Patent Publication No. WO 2016/154297.

In some specific examples, the biological control agent is for producing fengycin or plipastatin-type compound, iturin-type compound and/or surfactin-type compound. type) Bacillus subtilis or liquefied Bacillus amylolus strain of the compound. For background, please see the following review article: Ongena, M., et al., " Bacillus Lipopeptides: Versatile Weapons for Plant Disease Biocontrol," Trends in Microbiology, Vol 16, No. 3, March 2008, pp. 115-125. Bacillus strains capable of producing lipopeptides include Bacillus subtilis QST713 (available as SERENADE OPTI or SERENADE ASO, from Bayer CropScience LP, USA, with NRRL accession number B21661 and described in U.S. Patent No. 6,060,051), liquefied starch spores Bacillus strain D747 (available as Double Nickel™, from Certis, USA, with accession number FERM BP-8234 and described in US Patent No. 7,094,592); Bacillus subtilis MBI600 (available as SUBTILEX ^® from Becker, USA Underwood Company, EPA registration number 71840-8) ; Bacillus subtilis Y1336 (available as BIOBAC ^® WP, from Taiwan Bion-Tech Company, registered as a biofungicide in Taiwan, registration number 4764, 5454, 5096 and 5277) Bacillus liquefaction, especially strain FZB42 (available as RHIZOVITAL ^® from ABiTEP, Germany); and liquefied starch Bacillus subtilis variant FZB24 (available from Novozymes Biologicals Inc, Salem, Virginia or Syngenta Crop Protection, LLC in Greensboro, Northern California, is a fungicide TAEGRO ^® or TAEGRO ^® ECO (EPA registration number 70127-5); and

(B2) Fungi, such as: (B2.1) Coniothyrium minitans , especially the CON/M/91-8 strain (accession number DSM-9660; for example, Contans® from Bayer); (B2. 2) Metschnikowia fructicola , especially NRRL Y-30752 strain (such as Shemer®); (B2.3) Microsphaeropsis ochracea (such as Microx® from Prophyta); ( B2.5) Trichoderma ( Trichoderma spp. ), including Trichoderma atroviride (Trichoderma atroviride), described in the SC1 strain of International Patent Application No. PCT/IT2008/000196); (B2.6) Trichoderma spp. ( Trichoderma harzianum rifai ) KRL-AG2 strain (also known as T-22 strain, /ATCC 208479, such as PLANTSHIELD T-22G, Rootshield® and TurfShield, from BioWorks, USA); (B2.14) Gliocladium roseum ), 321U strain, from WF Stoneman Company LLC; (B2.35) Talaromyces flavus , V117b strain; (B2.36) Trichoderma asperellum , ICC 012 strain, from Isagro; ( B2.37) Trichoderma aculeatus SKT-1 strain (for example, ECO-HOPE®, from Kumiai Chemical Industry); (B2.38) Trichoderma dark green CNCM I-1237 strain (for example, Esquive® WP, from Agrauxine, FR) ; (B2.39) Trichoderma dark green strain number V08/002387; (B2.40) Trichoderma dark green strain NMI number V08/002388; (B2.41) Trichoderma dark green strain NMI number V08/002389; (B2 .42) Trichoderma dark green strain NMI number V08/002390; (B2.43) Trichoderma dark green strain LC52 (for example, Tenet from Agrimm Technologies Limited); (B2.44) Trichoderma dark green strain ATCC 20476 (IMI 206040) ); (B2.45) Trichoderma dark green strain T11 (IMI352941/ CECT20 498); (B2.46) Trichoderma harmatum ; (B2.47) Trichoderma harmatum; (B2.48) Trichoderma harmatum T39 (for example, Trichodex® from Makhteshim, USA); (B2. 49) Trichoderma harveyi, especially KD strains (eg Trichoplus, from Biological Control Products, SA (acquired by Becker Underwood)); (B2.50) Trichoderma harveyi ITEM 908 strain (eg Trianum-P from Koppert) ; (B2.51) Trichoderma harveyi TH35 strain (such as Root-Pro of Mycontrol); (B2.52) Trichoderma virens (also known as Gliocladium virens ), especially GL -21 strain (for example, SoilGard 12G of Certis, USA); (B2.53) Trichoderma viride , TV1 strain (for example, Trianum-P of Koppert); (B2.54) Ampelomyces quisqualis , Especially AQ 10 strains (such as AQ 10® from IntrachemBio Italia); (B2.56) Aureobasidium pullulans, especially budding spores of strain DSM14940; (B2.57) Aureobasidium pullulans, especially budding of DSM 14941 strain Spores; (B2.58) Aureobasidium pullulans, especially a mixture of spores of strains DSM14940 and DSM 14941 (for example, bio-ferm, CH's Botector®); (B2.64) Cladosporium cladosporioides ), H39 strain (from Stichting Dienst Landbouwkundig Onderzoek); (B2.69) Gliocladium catenulatum (synonym: Clonostachys rosea f. catenulate ) J1446 strain (for example, AgBio Inc. (B2.70) Lecanicillium lecanii (formerly known as Verticillium lecanii conidia ) KV01 strain (e.g. Kop) Vertalec® of pert/Arysta); (B2.71) Penicillium vermiculatum ; (B2.72) Pichia anomala WRL-076 strain (NRRL Y-30842); (B2.75) ) Trichoderma dark green SKT-1 strain (FERM P-16510); (B2.76) Trichoderma dark green SKT-2 strain (FERM P-16511); (B2.77) Trichoderma dark green SKT-3 strain ( FERM P-17021); (B2.78) Trichoderma gamsii (formerly T. viride ) ICC080 strain (IMI CC 392151 CABI, such as AGROBIOSOL DE MEXICO, BioDerma of SA DE CV); (B2.79 ) Trichoderma harveyi DB 103 strain (for example, T-Gro 7456 of Dagutat Biolab); (B2.80) Trichoderma polysporum (Trichoderma polysporum) IMI 206039 strain (for example, Binab TF WP of BINAB Bio-Innovation AB, Sweden); (B2.81) Trichoderma stromaticum (such as Trichoderma from Ceplac , Brazil); (B2.83) Ulocladium oudemansii , especially HRU3 strain (such as New Zealand Botry- Botry-Zen® of Zen Ltd); (B2.84) Verticillium albo-atrum (formerly V. dahliae ) WCS850 strain (CBS 276.92; such as Dutch Trig of Tree Care Innovations); (B2.86) Verticillium chlamydosporium (Verticillium chlamydosporium); (B2.87) A mixture of Trichoderma aculeatus ICC 012 strain and Trichoderma gaimus ICC 080 strain (the product is known as, for example, BIO-TAM ^{TM from Bayer CropScience LP, USA} ).

Other examples of biological control agents that can be combined with the compound of formula (I) and the composition comprising them are:

Bacteria selected from the group consisting of: Bacillus subtilis, especially Bacillus subtilis CNCM I-1562 strain and Bacillus firmus I-1582 strain (accession number CNCM I-1582), Bacillus subtilis OST 30002 (accession number NRRL B-50421), Bacillus thuringiensis ( Bacillus thuringiensis ), especially Bacillus thuringiensis subsp. israelensis (serotype H-14), strain AM65-52 (accession number ATCC 1276), Bacillus thuringiensis B. thuringiensis subsp. aizawai , especially ABTS-1857 strain (SD-1372), B. thuringiensis subsp. kurstaki HD-1 strain, Bacillus thuringiensis subsp. kurstaki B. thuringiensis subsp. tenebrionis NB 176 strain (SD-5428), Pasteuria penetrans , Pasteuria spp . (Rotylenchulus reniformis ))-PR3 (accession number ATCC SD-5834), Streptomyces microflavus AQ6121 strain (= QRD 31.013, NRRL B-50550) and Streptomyces galbus AQ 6047 strain (accession number NRRL 30232) );

Fungi and yeasts selected from the group consisting of: Beauveria bassiana , especially ATCC 74040 strain, Lecanicillium spp ., especially HRO LEC 12 strain, Black Anisopliae ( Metarhizium anisopliae ), especially F52 strain (DSM3884 or ATCC 90448), Paecilomyces fumosoroseus (currently: Isaria fumosorosea ), especially IFPC 200613 strain or Apopka 97 strain (Accession No. ATCC 20874) and Paecilomyces lilacinus , especially P. lilacinus 251 strain (AGAL 89/030550);

Viruses selected from the group consisting of: Adoxophyes orana (Summer leaf roller) granular disease virus (GV), codling moth ( Cydia pomonella ) (codling moth) granular disease virus (GV), Helicoverpa armigera (Helicoverpa armigera) (Helicoverpa armigera) nuclear polyhedrosis virus (NPV), Spodoptera exigua mNPV, Spodoptera frugiperda (Autumn march insect) mNPV and Spodoptera littoralis ) (African cotton leafworm) NPV.

Bacteria and fungi can be added to plants or plant parts or plant organs as inoculants, using their specific properties to improve plant growth and plant health. Examples are: Agrobacterium spp. , Azorhizobium caulinodans , Azospirillum spp. , Azotobacter spp. , Bradyrhizobium spp. ), Burkholderia spp. , especially Burkholderia cepacia (previously called Pseudomonas cepacia ), and Megacystis (Burkholderia cepacia) Gigaspora spp. ) or Gigaspora monosporum , Glomus spp. , Laccaria spp. , Lactobacillus buchneri , Glomus spp. Paraglomus spp. ), Pisolithus tinctorus , Pseudomonas spp. , Rhizobium spp. , especially Rhizobium trifolii , Rhizopogon spp. ), Scleroderma spp. , Suillus spp. and Streptomyces spp .

Plant extracts and products formed by microorganisms (including proteins and secondary metabolites) that can be used as biological control agents, such as garlic ( Allium sativum ), wormwood ( Artemisia absinthium ), azadirachtin, Biokeeper WP, Cassia nigricans , Celastrus angulatus , Chenopodium anthelminticum , Chitin, Armour-Zen, Dryopteris filix-mas , Equisetum arvense , Fortune Aza, Fungastop, Heads Up (quinoa (Chenopodium quinoa) saponin extract), pyrethrum (pyrethrum) / pyrethrins (pyrethrins), Surinam quassia (quassia amara), the genus oak (Quercus), genera Quillaja ( Quillaja ), Regalia, "Requiem ^TM Insecticide", rotenone, ryania /ryanodine, Symphytum officinale , Tanacetum vulgare , thymol ), Triact 70, TriCon, Nasturtium ( Tropaeulum majus ), Urtica dioica , Veratrin, Mistletoe ( Viscum album ), Brassicaceae ( Brassicaceae ) extracts, especially canola powder or mustard powder.

Examples of insecticides, acaricides and nematicides that can be mixed with the compound of formula (I) and the composition containing them are:

(1) Acetylcholinesterase (AChE) inhibitors, such as, for example, carbamates, such as alanycarb, aldicarb, bendiocarb, and benfuracarb, butoxycarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, butoxycarboxim Fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, metolcarb oxamyl), pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and methacarb xylylcarb); or organic phosphates, such as acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, Chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton -S-methyl), diazinon, dichlorvos/DDVP, diclotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, Heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate, isoxathion, Marathon ), mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, method Oxydemeton-methyl, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon ), phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, worship Quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, sanluo Pine (triazophos), trichlorfon (trichlorfon) and vamidothion (vamidothion).

(2) GABA-gated chloride channel blockers, such as, for example, cyclodiene-organochlorines, such as chlordane and endosulfan, or phenylpyrazole (phenanthrene Fiproles, such as ethiprole and fipronil.

(3) Sodium channel modulators, such as, for example, pyrethroids, such as acrinathrin, allethrin, iso-cis-trans-arenin, iso-trans-arenin, Bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, β- Cyhalothrin, λ-cyhalothrin, γ-cyhalothrin, cypermethrin, α-cyhalothrin, β-cyhalothrin, θ-cyhalothrin, ζ- Cyphenothrin, cyphenothrin [(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-(1R) isomer], Yihua Esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, hefen Ning (halfenprox), ipunin (imiprothrin), kadethrin, momfluorothrin, permethrin, phenothrin ((1R)-trans isomer), pyalenin ( prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin ( 1R)-isomer], tralomethrin and transfluthrin or DDT or methoxychlor.

(4) Nicotine acetylcholine receptor (nAChR) competitive modulators, such as, for example, neonicotinoids, such as acetamiprid, clothianidin, dinotefuran , Imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.

(5) Allosteric modulators of nicotine acetylcholine receptor (nAChR), such as, for example, spinosyn, such as spinetoram and spinosad.

(6) Glutamate-gated chloride channel (GluCl) allosteric modulators, such as, for example, avermectin/milbemycin, such as abamectin, Emmectin benzoate, lepimectin and milbemectin.

(7) Juvenile hormone mimics, for example, for example, juvenile hormone analogs, such as hydroprene, kinoprene and methoprene or fenoxycarb or Pyriproxyfen.

(8) Hybrid non-specific (multi-site) inhibitors, such as, for example, alkyl halides such as methyl bromide and other alkyl halides; or chloropicrin (Chloropicrin) or sulfuryl fluoride (sulfuryl fluoride) fluoride or borax or tartar emetic or methyl isocyanate generators, such as dazomet and meta.

(9) String tone sensory organ modulators, such as, for example, pymetrozine or flonicamid.

(10) Mite growth inhibitors, for example, clofentezine, hexythiazox, diflovidazin or etoxazole.

(11) Microbial interference agents for insect intestinal membranes, such as, for example, Bacillus thuringiensis subsp. Israel, Bacillus sphaericus , Bacillus thuringiensis subsp. Catalpa, Bacillus thuringiensis subsp. Kustaji Subspecies, Bacillus thuringiensis subsp. Paediatrics, and Bacillus thuringiensis plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/35Ab1.

(12) Inhibitors of mitochondrial ATP synthase, such as ATP disruptors, such as, for example, diafenthiuron or organotin compounds, such as azocyclotin, cyhexatin and Fenbutatin oxide or Propargite or Tetradifon.

(13) Oxidative phosphorylation decoupling agents that disrupt the effect of the proton gradient, such as, for example, chlorfenapyr, DNOC, and sulfluramid.

(14) Nicotine acetylcholine receptor channel blockers, such as, for example, bensultap, cartap hydrochloride, thiocyclam and thiosultap- sodium).

(15) Chitin biosynthesis inhibitor, type 0, for example, for example, bitrifluron, chlofluazuron, diflubenzuron, flucycloxuron, Flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

(16) Chitin biosynthesis inhibitor, type 1, such as buprofezin.

(17) Moulting disruptors (especially Diptera), such as, for example, cyromazine.

(18) ecdysone receptor agonists, such as, for example, chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

(19) Octopamine receptor agonists, such as, for example, amitraz.

(20) Mitochondrial complex III electron transport inhibitors, such as, for example, hydramethylnon or acequinocyl or fluacrypyrim.

(21) Mitochondrial complex I electron transport inhibitors, for example, from the group of METI acaricides, such as fenazaquin, fenpyroximate, pyrimidifen, Pyidaben, tebufenpyrad and tolfenpyrad or rotenone (Derris).

(22) Voltage-dependent sodium channel blockers, such as, for example, indoxacarb or metaflumizon.

(23) Inhibitors of acetyl-CoA carboxylase, such as, for example, tetronic acid and tetramic acid derivatives, such as spirodiclofen and spirodiclofen (spiromesifen) and spirotetramate (spirotetramate).

(24) Mitochondrial complex IV electron transport inhibitors, such as, for example, phosphines, such as aluminum phosphide, calcium phosphide, phosphine and zinc phosphide, or cyanides, such as calcium cyanide, potassium cyanide And sodium cyanide.

(25) Mitochondrial complex II electron transport inhibitors, such as, for example, β-ketonitrile derivatives, such as cyenopyrafen and cyflumetofen, and formanilines, for example, For example, pyflubumide.

(28) Ryanodine receptor modulators, such as, for example, diamides such as chlorantraniliprole, cyantraniliprole and flubendiamide,

Additional active compounds, such as, for example, Afidopyropen, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Broflanilide, Bromopropylate, Chinomethionat, Chloroprallethrin, Cryolite, Ring Cyclaniliprole, Cycloxaprid, Cyhalodiamide, Dicloromezotiaz, Diclofol, Epsilon Metofluthrin, ε- Trifluthrin monomer, Flometoquin, Fluazaindolizine, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprole , Fluhexafon, Fluopyram, Fluralaner, Fluzametamide, Fufenozide, Guadipyr, Heptafluthrin, Chlorothialine (Imidaclothiz), Iprodione, Kappa-Bifenthrin, Kappa-Tefluthrin, Lotilaner, Meperfluthrin, Paichongding, Three Pyridalyl, Pyrifluquinazon, Pyriminostrobin, Spirobudiclofen, Tetramethylfluthrin, Tetraniliprole, Tetrachlorantraniliprole, Tigolaner, Tioxazafen, Sulfoxime (Thiofluoximate), Triflumezopyrim (Triflumezopyrim) and Methyliodide (Methyliodide); in addition, preparations based on Bacillus firmus (I-1582, BioNeem, Votivo) and the following compounds: 1-{2-Fluoro-4 -A Group-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl)-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine( Obtained from WO2006/043635) (CAS 885026-50-6), {1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[ Indole-3,4'-piperidine)-1(2H)-yl)(2-chloropyridin-4-yl)methanone (from WO2003/106457) (CAS 637360-23-7), 2-chloro -N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)benzene Base) isonicotinamide (from WO2006/003494) (CAS 872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy -1,8-diazaspirocyclo[4.5]dec-3-en-2-one (derived from WO 2010052161) (CAS 1225292-17-0), 3-(4-chloro-2,6-dimethyl Phenyl)-8-methoxy-2-oxo-1,8-diazaspirocyclo[4.5]dec-3-en-4-yl ethyl carbonate (derived from EP2647626) (CAS 1440516-42 -6), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (derived from WO2004/099160) ( CAS 792914-58-0), PF1364 (derived from JP2010/018586) (CAS 1204776-60-2), N-[(2E)-1-[(6-chloropyridin-3-yl)methyl)pyridine- 2(1H)-subunit]-2,2,2-trifluoroacetamide (derived from WO2012/029672) (CAS 1363400-41-2), (3 E )-3-[1-[(6- (Chloro-3-pyridyl)methyl)-2-pyridinylene)-1,1,1-trifluoro-propan-2-one (derived from WO2013/144213) (CAS 1461743-15-6), N -[3-(Benzylaminomethyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1 H -pyrazole- 5-methylamide (derived from WO2010/051926) (CAS 1226889-14-0), 5-bromo-4-chloro- N -[4-chloro-2-methyl-6-(methylaminomethanyl )Phenyl)-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide (derived from CN103232431) (CAS 1449220-44-3), 4-(5-(3,5-二(Chlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl)-2-methyl- N- ( cis - 1-oxo-3-thiapinyl) )-Benzamide, 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methan yl - N - (trans - l-oxido Da -3-yl) - amine and benzoyl 4 - [(5 S) -5- (3,5- dichlorophenyl) -4,5-dihydro- -5-(trifluoromethyl)-3-isoxazolyl)-2-methyl- N- ( cis - 1-oxo-3-thiapidinyl)benzamide (derived from WO 2013/050317 A1 ) (CAS 1332628-83-7), N -[3-chloro-1-(3-pyridyl)-1 H -pyrazol-4-yl] -N -ethyl-3-[(3,3, 3-Trifluoropropyl)sulfinyl]-propionamide, (+)- N -[3-chloro-1-(3-pyridinyl)-1 H -pyrazol-4-yl]- N- Ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide and (-)- N -[3-chloro-1-(3-pyridyl)-1 H -Pyrazol-4-yl] -N -ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide (derived from WO 2013/162715 A2, WO 2013/ 162716 A2, US 2014/0213448 A1) (CAS 1477923-37-7), 5-[[(2 E )-3-chloro-2-propen-1-yl]amino)-1-[2,6- Dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl) sulfinyl]-1 H -pyrazole-3-carbonitrile (derived from CN 101337937 A) (CAS 1105672 -77-2), 3-bromo- N -[4-chloro-2-methyl-6-[(methylamino)thiomethanoyl]phenyl]-1-(3-chloro-2- pyridinyl) -1 H - pyrazole-5-Amides, (Liudaibenjiaxuanan, available from CN 103109816 A) (CAS 1232543-85-9) ; N - [4- chloro-2 - [[(1,1 (Dimethylethyl)amino)carbonyl)-6-methylphenyl)-1-(3-chloro-2-pyridyl)-3-(fluoromethoxy)-1 H -pyrazole-5- Formamide (derived from WO 2012/034403 A1) (CAS 1268277-22-0), N -[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro 6-methylphenyl] -3-bromo-1- (3-chloro-2-pyridinyl) -1 H - pyrazole-5-acyl-amine (available from WO 2011/085575 A1) (CAS 1233882- 22-8), 4-[3-[2,6-Dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2 -Methoxy-6-(trifluoromethyl)-pyrimidine (derived from CN 10 1337940 A) (CAS 1108184-52-6); (2 E )- and 2( Z )-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl ] ethylidene] - N - [4- (difluoromethoxy) phenyl] - Amides carbazate (available from CN 101715774 A) (CAS 1232543-85-9) ; 3- (2,2- Dichlorovinyl)-2,2-dimethyl-4-( 1H -benzimidazol-2-yl)phenyl-cyclopropanecarboxylate (derived from CN 103524422 A) (CAS 1542271-46-4 ); (4a S )-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]- Indeno[1,2-e][1,3,4]㗁di𠯤-4a(3 H )-carboxylic acid methyl ester (from CN 102391261 A) (CAS 1370358-69-2); 6-deoxy -3- O -ethyl-2,4-bis- O -methyl-, 1-[ N -[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy )Phenyl]-1 H -1,2,4-triazol-3-yl)phenyl)carbamate)-α-L-mannanose (derived from US 2014/0275503 A1) (CAS 1181213 -14-8); 8-(2-Cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-ta𠯤-3-yl)-3- Aza-bicyclo[3.2.1]octane (CAS 1253850-56-4), (8-reverse)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)- 3-(6-Trifluoromethyl-ta𠯤-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS 933798-27-7), (8-same)-8-(2 -Cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-ta𠯤-3-yl)-3-aza-bicyclo[3.2.1]octane Alkane (from WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8), N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl 3-[(3,3,3-trifluoropropyl)thio]-propanamide (derived from WO 2015/058021 A1, WO 2015/058028 A1) (CAS 1477919-27-9) and N- [4-(Aminothiomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridyl)- 1 H -pyrazole-5-carboxamide (derived from CN 103265527 A) (CAS 1452877-50-7), 5-(1,3-two 㗁𠮿-2-yl)-4- [[4-(Trifluoromethyl)phenyl]methoxy]-pyrimidine (from WO 2013/115391 A1) (CAS 1449021-97-9), 3-(4-chloro-2,6-dimethyl Phenyl)-4-hydroxy-8-methoxy-1-methyl-1,8-diazaspirocyclo[4.5]dec-3-en-2-one (derived from WO 2010/066780 A1, WO 2011/151146 A1) (CAS 1229023-34-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-1,8-diazepine Heterospiro[4.5]decane-2,4-dione (from WO 2014/187846 A1) (CAS 1638765-58-8), 3-(4-chloro-2,6-dimethylphenyl)- 8-Methoxy-1-methyl-2-oxo-1,8-diaza spiro [4.5] dec-3-en-4-yl-ethyl carbonate (from WO 2010/066780 A1, WO 2011151146 A1) (CAS 1229023-00-0), N-[1-[(6-chloro-3-pyridyl)methyl]-2(1 H )-pyridinylene]-2,2,2- Trifluoro-acetamide (derived from DE 3639877 A1, WO 2012029672 A1) (CAS 1363400-41-2), [N( E )]-N-[1-[(6-chloro-3-pyridyl)methyl Group]-2(1H)-pyridinylene]-2,2,2-trifluoro-acetamide, (from WO 2016005276 A1) (CAS 1689566-03-7), [N( Z )]-N -[1-[(6-Chloro-3-pyridyl)methyl]-2(1H)-pyridinylene]-2,2,2-trifluoro-acetamide (CAS 1702305-40-5), 3-Endo-3-[2-propoxy-4-(trifluoromethyl)phenoxy]-9-[[5-(trifluoromethyl)-2-pyridyl]oxy]-9- Azabicyclo[3.3.1]nonane (derived from WO 2011/105506 A1, WO 2016/133011 A1) (CAS 1332838-17-1).

Examples of safeners that can be mixed with compounds of formula (I) and compositions containing them include, for example, benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide, Dichlormid, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole , Isoxadifen-ethyl (isoxadifen-ethyl), mefenpyr-diethyl, naphthalic anhydride, oxabetrinil, 2- Methoxy-N-({4-[(methylaminomethylamino]phenyl)sulfonyl)benzamide (CAS 129531-12-0), 4-(dichloroacetamide) -1-oxa-4-azaspirocyclo[4.5]decane (CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3- Zazolidine (CAS 52836-31-4).

    Examples of herbicides that can be mixed with the compound of formula (I) and the composition containing them are: acetochlor, acifluorfen, acifluorfen-sodium, aclonifen (aclonifen), alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, first Amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylate Acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate ), anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, grass Benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, benfluralin Bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos , Bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, Bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate and -octanoate), busoxinone, butachlor, butafenacil , Butamifos, butenachlor, butalin, butroxydim, butachlor (butylate), carfentrazone (caf enstrole), carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, carfentrazone (chlorfenac), chlorfenac-sodium, oat ester (chlorfenprop), chlorflurenol, (methyl) chlorflurenol-methy, chloridazon, chlorimuron (chlorimuron), (ethyl) chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorosulfuron ( chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, Clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clodinafop-propargyl (cloransulam), cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfuron (cyclosulfamuron), cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butoxy Ethyl, -butyl, -dimethylammonium, -diolamine, -ethyl, -2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -tri Ammonium isopropoxide and -triethanolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium, Daimuron (daimuron/dymron), Raben (dalapon), cotton (dazomet), n-decyl alcohol, beet an (desmedipham), detosyl-pyrazolate (DTP), dicamba (dicamba), diquan (dic hlobenil), 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl) -4,4-Dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, dichlorprop-P, diclofop, dichlorprop- P-methyl, diclosulam (diclosulam), difenzoquat (difenzoquat), diflufenican (diflufenican), diflufenzopyr (diflufenzopyr), flumizone-sodium, oxazolone (dimefuron) ), dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, Dinitramine; dinoterb; diphenamid; diquat, diquat-dibromid, dithiopyr; dinoterb diuron), DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, Ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, ethoxyflufen (etobenzanid), F-9600, F-5231, that is, N-{2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-5-oxo-4,5-dihydro- 1H-tetrazol-1-yl]phenyl}ethanesulfonamide, F-7967, which is 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazole-4 -Yl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoxaprop, fenoxaprop-P, ( Ethyl) fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, fenoxaprop-P-ethyl Ester (flamp rop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-P Fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, fluazifop-P-butyl, flucarbazone-sodium, fluazifop-P-butyl flucetosulfuron), fluchloralin, flufenacet, flufenpyr, (ethyl) flufenpyr-ethyl, flumetsulam ), flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flumiclorac-pentyl, -Dimethyl ammonium and methyl ester, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl Base-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, oxazine Methyl oxalate (fluthiacet-methyl), fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, fomesafen -Ammonium, Glyphosate-P-sodium, Glyphosate-P-ammonium, Glyphosate, Glyphosate, Glyphosate-ammonium, -isopropyl-ammonium, -diammonium , -Dimethylammonium, -potassium, -sodium, and -trimethylsulfide, H-9201, which is O-(2,4-dimethyl-6-nitrophenyl) O-ethyl iso Propylamino phosphorothioate, halauxifen, halauxifen, halauxifen-methyl, halosafen, halosulfuron, methyl chlorpyrisulfuron , Haloxyfop, Haloxyfop-P, Haloxyfop-ethoxyethyl, Haloxyfop-P-B Oxyethyl (haloxyfop-P-ethoxyethyl), methyl chlorofluoro (haloxyfop-methyl), chlorofluoro-P-methyl (haloxyfop-P-methyl), hexazinone, HW-02 i.e. 1-(Dimethoxyphosphoryl)ethyl-(2,4-dichlorophenoxy)acetate, imazamethabenz, imazamethabenz-methyl, methoxysulfuron (imazamox), methoxysulfuron-ammonium, methoxysulfuron-methyl (imazapic), methoxysulfuron-ammonium (imazapic-ammonium), imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, Imazaquin, imazolinic acid-ammonium, imazethapyr, imazolinic acid-ammonium, imazosulfuron, indanofan, indaziflam, iodoform Iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-caprylic acid, -potassium and -sodium, ipfencarbazone, isopropalin , Isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, which is 3-({ [5-(Difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl)sulfonyl)-5,5-dimethyl-4 ,5-Dihydro-1,2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butoxyethyl, -dimethyl Base ammonium, -2-ethylhexyl, -isopropylammonium, -potassium and -sodium, MCPB, MCPB-methyl, ethyl and -sodium, mecoprop, dimethyltetrachloropropionate Acid-sodium and-butoxyethyl, dimethyltetrachloropropionic acid-P, dimethyltetrachloropropionic acid-P-butoxyethyl, -dimethylammonium, -2-ethylhexyl ester and -potassium, Mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methyl Methabenzthiazuron, metam, metamifop, metamitron, metametachlor zachlor), metazosulfuron (metazosulfuron), methabenzthiazuron, methiopyrsulfuron (methiopyrsulfuron), metiozolin, methyl isothiocyanate, bromosulfuron (metobromuron), isopropyl methyl Metolachlor, S-metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron, Metsulfuron -Methyl, molinate, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, also known as N-(3-chloro-4 -Isopropylphenyl)-2-methylpentanamide, NGGC-011, napropamide, NC-310, that is [5-(benzyloxy)-1-methyl-1H-pyridine (Azol-4-yl)(2,4-dichlorophenyl)methanone, neburon, nicosulfuron, pelargonic acid (pelaric acid), norflurazon, oil Acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, episulfuron oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, pendimethalin (penoxsulam), pentachlorphenol, pentoxazone, pethoxamid, petroleum, phenmedipham, picloram, fluopyram ( picolinafen), pinoxaden (pinoxaden), piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, metflurazin ( prodiamine, profoxydim, prometon, prometryn, propach lor), propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propasulfuron-sodium (propoxycarbazone-sodium), propyrisulfuron (propyrisulfuron), propyzamide (propyzamide), prosulfocarb, prosulfuron (prosulfuron), pyraclonil (pyraclonil), metafentrazone ( pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen ), pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, cyclic ester Pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium ), pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quinofop, ethyl fast Quizalofop-ethyl, quizalofop-P (quizalofop-P), quizalofop-P-ethyl (quizalofop-P-ethyl), quizalofop-P-tefuryl, rimsulfuron (rimsulfuron), saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, Sulfentrazone (sulfentrazone), sulfometuron (sulfometuron), metsulfuron (s ulfometuron-methyl), sulfasulfuron (sulfosulfuron), SYN-523, SYP-249, namely 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2 -Chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, that is, 1-[7-fluoro-3-oxo-4-(prop-2- (Alkyn-1-yl)-3,4-dihydro-2H-1,4-benzos-6-yl)-3-propyl-2-thiimidazole-4,5-dione, 2, 3,6-TBA, TCA (trichloroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, tebuthiuron (terbacil), terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazol Thiazopyr, thiencarbazone, thifensulfuron-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, fenpyrazone (topramezone), tralkoxydim, triafamone, triallate, triasulfuron, triaziflam, tribenuron, Tribenuron-methly, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, fluorine Trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, That is, 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, and the following compounds:

Examples of plant growth regulators are: Acibenzolar, Acibenzolar, S-methyl, 5-aminolevulinic acid, ancymidol, 6- Benzylaminopurine, Brassinolide, catechine, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop) Prop-1-enyl) propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium , Endothal (endothal), Endothal-dipotassium,-disodium, and-mono (N, N-dimethyl alkyl ammonium), ethephon (ethephon), flumetralin (flumetralin), fluorenidine Acid (flurenol), fluorenbutyric acid-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA ), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, maleic hydrazide, mepiquat chloride ), 1-methylcyclopropene, methyl jasmonate, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthoxyacetic acid, nitrophenate-mixture, paclobutrazol , N-(2-phenylethyl)-β-alanine, N-phenylphthalamide, prohexadione, prohexadione-calcium, prohydrojasmone , Salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, Uniconazole, Uniconazole-P. Method and use

The compound of formula (I) and the composition containing them have potent microbicidal activity. It can be used to control unwanted microorganisms, such as unwanted fungi and bacteria. It is particularly useful for crop protection (controlling microorganisms that cause plant diseases) or protecting materials (for example, industrial materials, wood, storage) as described in more detail below. More specifically, the compound of formula (I) and the composition containing them can be used to protect seeds, germinating seeds, seedlings, plants, plant parts, fruits, harvests and/or soils where plants grow from undesirable microorganism.

Control as used in the text includes the protection, treatment and eradication of unwanted microorganisms. Undesirable microorganisms can be pathogenic bacteria, pathogenic viruses, pathogenic oomycetes or pathogenic fungi, more specifically phytopathogenic bacteria, phytopathogenic viruses, phytopathogenic oomycetes or phytopathogenic fungi. As detailed below, these phytopathogenic microorganisms are pathogens that cause a wide range of plant diseases.

More specifically, the compounds of formula (I) and compositions containing them can be used as fungicides. For the purpose of this specification, the term "fungicide" refers to crop protection for the control of unwanted fungi, such as Plasmodiophoromycetes, Chytridiomycetes, Zygomycetes, and Ascomycetes. (Ascomycetes), Basidiomycetes and Deuteromycetes and/or compounds or compositions used to control Oomycetes, more preferably used to control Basidiomycetes (causing rust).

The present invention also relates to a method for controlling unwanted microorganisms, such as phytopathogenic fungi, oomycetes and bacteria, which method comprises applying at least one compound of formula (I) or at least one composition comprising them to the microorganisms and/ Or its habitat (applied to plants, plant parts, seeds, fruits or the soil where the plants grow).

Typically, when the compounds and compositions of the present invention are used in treatment or protection methods for the control of phytopathogenic fungi and/or phytopathogenic oomycetes, they are effective and plant-compatible to be applied to plants, plants The soil or substrate where the parts, fruits, seeds, or plants grow. Suitable substrates that can be used to grow plants include inorganic substrates, such as mineral wool, especially rock wool, nacre, sand or gravel; organic substrates, such as peat, pine bark, or sawdust; and petroleum-based substrates, such as polymer foam Or plastic beads. The effective and plant-compatible capacity is an amount sufficient to control or destroy fungi that exist or may appear in the field, and the amount does not cause any perceptible symptoms of phytotoxicity to the crop. This amount can vary within a wide range according to the fungi to be controlled, the type of crop, the growth stage of the crop, the climatic conditions and the individual compound or composition of the present invention used. This amount can be determined by systematic field experiments within the ability of those who are familiar with this technique. Plants and plant parts

The compound of formula (I) and the composition containing them can be applied to any plant or plant part.

Plants refer to all plants and plant groups, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants that can be obtained by conventional breeding and optimization methods or by biotechnology and genetic engineering methods or a combination of these methods, including genetically modified plants (GMO or genetically modified plants) and plant breeding with or without recipients Plant cultivars protected by family rights.

Please understand that plant parts refer to all the above-ground and underground plant parts and organs of plants, such as buds, leaves, flowers and roots. Examples include leaves, thorns, stems, stems, flowers, fruit bodies, fruits and seeds, and roots. , Tubers and underground stems. Plant parts also include harvested materials and asexual and reproductive propagation materials, such as cuttings, tubers, underground stems, stalks, and seeds.

The plant lines that can be treated according to the method of the present invention include the following plants: cotton, flax, grapes, fruits, vegetables, such as Rosaceae sp . (for example, pome fruits such as apples and pears, and stone fruits such as apricots and cherries , Almonds and peaches, and berries such as strawberries), Ribesioidae sp. , Juglandaceae sp. , Betulaceae sp. , Anacardiaceae sp. , Fagaceae ( Fagaceae sp. ), Moraceae ( Moraceae sp .), Oleaceae (Oleaceae sp. ), Actinidaceae sp ., Lauraceae sp. , Musaceae sp. ) (such as banana trees and Banana garden), Rubiaceae sp. (such as coffee), Camellia ( Theaceae sp. ), Sterculiceae sp. , Rutaceae sp. (such as lemon, orange and grapefruit); Solanaceae ( Solanaceae sp.) (e.g. tomato), Liliaceae ( Liliaceae sp. ), Asteraceae sp. (e.g. lettuce), Umbelliferae ( Umbelliferae sp. ), Cruciferae sp. ), Chenopodiaceae sp. , Cucurbitaceae sp. (e.g. cucumber), Alliaceae sp. (e.g. leek, onion), Papilionaceae sp. ) (e.g. pea ); major crop plants, such as Gramineae sp. (such as corn, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale), Asteraceae sp. (such as sunflower ), Brassicaceae ( Brassicaceae sp .) (such as head cabbage, red cabbage, green cauliflower, white cauliflower, broccoli, cabbage, kohlrabi, radish and rape, mustard, horseradish and cress), Leguminous ( Fabacae sp. ) (such as kidney beans, peanuts), butterfly flowers (such as soybeans), Solanaceae (such as potatoes), Chenopodiaceae (such as sugar beet, fodder beet, Swiss chard, beetroot); garden and Useful plants and ornamental plants in woodland; and their respective genetically modified species.

In some preferred embodiments, wild plant varieties and plant cultivars or these plants obtained by conventional biological breeding methods, such as crossover or protoplasmic fusion, and their parts are processed according to the method of the present invention.

In some other preferred embodiments, genetically modified plants and plant cultivars (genetically modified organisms), and their parts, obtained by combining genetic engineering methods, if appropriate, with conventional methods, are processed according to the method of the present invention. . More preferably, plants of plant cultivars that are commercially available or in use are processed according to the method of the present invention. Please understand that plant cultivars refer to plants that have novel characteristics ("traits") and are obtained by conventional breeding, gene mutation or recombinant DNA technology. The plant can be cultivars, varieties, biotypes and genotypes.

The method according to the invention can be used to treat genetically modified organisms (GMO), such as plants or seeds. Generally speaking, a genetically modified plant (or genetically transgenic plant) is a plant in which a heterologous gene has been stably integrated into the genome. The term "heterologous gene" basically refers to a gene provided or assembled outside the plant, and when introduced into the nucleus, chloroplast or mitochondrial gene body, by expressing favorable proteins or polypeptides, or by down-regulation, silence Other genes present in the plant (using, for example, antisense technology, co-suppression technology, RNA interference-RNAi-technology or microRNA-miRNA-technology) impart new or improved agronomic or other characteristics to the transformed plant. Heterologous genes located in the genome are also called transgenic genes. A transgenic line defined by its location in the plant genome is called a transformed or transgenic line.

The plants and plant cultivars that can be processed by the methods disclosed above include all plants (whether or not they are obtained by breeding and/or biotechnology methods) that have genetic material that gives these plants particularly advantageous and useful characteristics. .

Plants and plant cultivars that can be treated by the methods disclosed above include plants and plant cultivars that resist one or more biological stresses, that is, the plants exhibit better resistance to animal and microbial pests, such as resistance to nematodes, insects, Defense against mites, phytopathogenic fungi, bacteria, viruses and/or viroids.

Plants and plant cultivars that can be processed by the methods disclosed above include the plants that resist one or more abiotic stresses. Abiotic stress conditions can include, for example, drought, low temperature exposure, heat exposure, osmotic pressure, floods, increased soil salinity, increased mineral exposure, ozone exposure, strong light exposure, limited availability of nitrogen nutrients, limited availability Phosphorus nutrients, shadow masking.

Plants and plant cultivars that can be processed by the methods disclosed above include plants that are characterized by improved yield characteristics. The increase in yield in the plant may be, for example, the result of improving plant physiology, growth and development, such as water use efficiency, water retention efficiency, nitrogen utilization, carbon assimilation, photosynthesis, germination efficiency, and accelerated maturation. Yield may be further affected by increased plant architecture (under stress and non-stress conditions), including, but not limited to, early flowering, flowering control to produce hybrid seeds, seedling vigor, plant size, number and distance of nodes , Root growth, seed size, fruit size, pod size, number of pods or ears, number of seeds per pod or ear, seed weight, increase seed fullness, reduce seed scattering, reduce pod splitting and lodging resistance. Further yield traits include seed composition, such as carbohydrate content and composition, such as cotton or starch, protein content, oil content and composition, nutritional value, reduction of anti-nutritional compounds, improved processability, and better storage stability.

Plants and plant cultivars that can be treated by the methods disclosed above include hybrid plants that have exhibited the characteristics of heterosis or hybrid vigor, which usually result in higher yields, vigor, health, and resistance to biological and abiotic stress. The plants and plant cultivars.

Plants and plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can be treated by the methods disclosed above include herbicide-tolerant plants, even plants that are tolerant to one or more specific herbicides And plant cultivars. These plants can be obtained by genetic transformation or by selecting plants containing mutations that confer tolerance to the herbicide.

Plants and plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can be treated by the methods disclosed above include genetically engineered plants that are resistant to insects, even plants and plants that are resistant to attack by specific target insects Cultivars. These plants can be obtained by genetic transformation or by selection of plants containing mutations that confer resistance to this insect.

Plants and plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can be treated by the methods disclosed above include plants and plant cultivars that are resistant to abiotic stress. These plants can be obtained by genetic transformation or by selecting plants containing mutations that confer this pressure resistance.

Plants and plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can be processed by the methods disclosed above include changes in the quantity, quality, and/or storage stability of harvested products, and/or changes in harvested products Plants and plant cultivars with altered properties of specific ingredients.

Plants and plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can be processed by the methods disclosed above include, for example, plants and plant cultivars of cotton with altered fiber properties. These plants can be obtained by genetic transformation or by selection of plants containing mutations that confer this altered fiber properties.

Plants and plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can be processed by the methods disclosed above include, for example, oilseed rape with altered oil properties or related Chinese kale (Brassica) Plants and plant varieties of plants. These plants can be obtained by genetic transformation or by selection of plants containing mutations that confer changes in the oil properties.

Plants and plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can be treated by the methods disclosed above include, for example, rapeseed with altered seed shattering characteristics or related Chinese kale plants and plants Cultivars. Such plants can be obtained by genetic transformation or by selection of plants containing mutations that confer changes in the seed shattering characteristics and include, for example, plants with rape plants that delay or reduce seed shattering.

Plants and plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can be processed by the methods disclosed above include, for example, plants and plant cultivars of tobacco plants with altered post-translational protein modification patterns. Pathogens and diseases

The method disclosed above can be used to control microorganisms, especially phytopathogenic microorganisms, such as phytopathogenic fungi that cause diseases, such as:

Diseases caused by powdery mildew pathogens, such as Blumeria [e.g. Blumeria graminis], Podosphaera [e.g. Podosphaera leucotricha], Sphaerotheca [e.g. Sphaerotheca fuliginea], Uncinula [e.g. Uncinula necator];

Diseases caused by rust pathogens, such as Gymnosporangium [e.g. Gymnosporangium sabinae ], Hemileia [e.g. Hemileia vastatrix ], Phytophthora (Phakopsora) [such as soybean rust layer (Phakopsora pachyrhizi) horse or mountain locust layer of rust (Phakopsora meibomiae)], Puccinia (Puccinia) [such as wheat leaf rust (Puccinia recondite), Puccinia wheat (Puccinia graminis or Puccinia striiformis ], Uromyces [such as Uromyces appendiculatus ];

Diseases caused by pathogens from the oomycete group, such as Albugo [e.g. Algubo candida], Bremia [e.g. Bremia lactucae )], Peronospora [such as Peronospora pisi or P. brassicae], Phytophthora [such as Phytophthora infestans] , Plasmopara [such as Plasmopara viticola], Pseudoperonospora [such as Pseudoperonospora humuli or Pseudoperonospora cubensis], Pythium Genus (Pythium) [e.g. Pythium ultimum];

Leaf spot and leaf blight caused by the following, such as Alternaria (for example, Alternaria solani), Cercospora (for example, Cercospora beets ( Cercospora beticola)], Cladosporum [e.g. Cladosporium cucumerinum], Cochliobolus [e.g. Cochliobolus sativus] (conidial form: Drechslera, synonym: Helminthosporium or Cochliobolus miyabeanus], Colletotrichum [for example, Colletotrichum lindemuthanium] , Cycloconium [e.g. Cycloconium oleaginum], Diaporthe [e.g. Diaporthe citri], Elsinoe [e.g. citrus Elsinoe fawcettii], Gloeosporium [e.g. Gloeosporium laeticolor], Glomerella [e.g. Glomerella cingulata] ], Guignardia [e.g. Guignardia bidwelli], Leptosphaeria [e.g. Leptosphaeria maculans], Magnaporthe [E.g. Magnaporthe grisea], Microdochium [e.g. Microdochium nivale], Mycosphaerella [e.g. Mycosphaerella graminicola, Mycosphaerella arachidicola and Mycosphaerella fijiensis], Phaeosphaeria [e.g. Phaeosphaeria nodorum], Pyre nophora) [e.g. Pyrenophora teres or Pyrenophora tritici repentis], Ramularia [e.g. (Ramularia collo-cygni) or Ramularia areola] , Rhynchosporium [e.g. Rhynchosporium secalis], Septoria [e.g. Septoria apii or Septoria lycopersi], more Stagonospora [e.g. Stagonospora nodorum], Typhula [e.g. Typhula incarnate], Venturia [e.g. Apple Black Star (Venturia inaequalis)],

Root and stem diseases caused by, for example, Corticium [e.g. Corticium graminearum], Fusarium [e.g. Fusarium oxysporum], Gaeumannomyces [e.g. Gaeumannomyces graminis], Plasmodiophora [e.g. Plasmodiophora brassicae], Rhizoctonia [e.g. stand Rhizoctonia solani, Sarocladium [e.g. Sarocladium oryzae], Sclerotium [e.g. Sclerotium oryzae], eye spots Tapesia [such as Tapesia acuformis], Thielaviopsis [such as Thielaviopsis basicola];

Diseases of ears and inflorescences (including corn cobs) caused by the following, such as Alternaria (for example, Alternaria spp.), Aspergillus (for example, Aspergillus flavus) )], Cladosporium [e.g. Cladosporium cladosporioides], Claviceps [e.g. Claviceps purpurea], Fusarium [e.g. Fusarium culmorum], Gibberella [e.g. Gibberella zeae], Monographella [e.g. Monographella nivalis], Ascopolyspora Genus (Stagonospora) [for example, Stagonospora nodorum];

Diseases caused by smut fungi, such as Sphacelotheca [e.g. Sphacelotheca reiliana], Tilletia [e.g. Tilletia caries ) Or Tilletia controversa], Urocystis [e.g. Urocystis occulta], Ustilago [e.g. Ustilago nuda)];

Fruit rot caused by the following, such as Aspergillus [such as Aspergillus flavus], Botrytis [such as Botrytis cinerea], Penicillium [ For example Penicillium expansum or Penicillium purpurogenum], Rhizopus [e.g. Rhizopus stolonifer], Sclerotinia (e.g. Sclerotinia sclerotiorum) (Sclerotinia sclerotiorum)], Verticilium [such as Verticilium alboatrum];

Seed and soil-borne rot and blight caused by the following, as well as diseases of seedlings, such as Alternaria [such as Alternaria brassicicola], Aphanomyces [E.g. Aphanomyces euteiches], Ascochyta [e.g. Ascochyta lentis], Aspergillus [e.g. Aspergillus flavus], Cladosporium [e.g. Cladosporium herbarum], Cochliobolus [e.g. Cochliobolus sativus] (conidial form: Drechsleria ( Drechslera, Bipolaris, Synonym: Helminthosporium])], Colletotrichum [for example, Colletotrichum coccodes], Fusarium (Fusarium) [e.g. Fusarium culmorum], Gibberella [e.g. Gibberella zeae], Macrophomina [e.g. Macrophomina phaseolina] ], Microdochium [e.g. Microdochium nivale], Monographella [e.g. Monographella nivalis], Penicillium [ For example, Penicillium expansum], Phoma [e.g. Phoma lingam], Phomopsis [e.g. Phomopsis sojae] , Phytophthora [e.g. Phytophthora cactorum], Pyrenophora [e.g. Pyrenophora graminea], Pyricularia [e.g. Rice Blast ( Pyricularia oryzae)], Pythium (Pythium) [e.g. Pythium ulti mum)], Rhizoctonia [e.g. Rhizoctonia solani], Rhizopus [e.g. Rhizopus oryzae], Sclerotium [e.g. White Sclerotium rolfsii], Septoria [e.g. Septoria nodorum], Typhula [e.g. Typhula incarnata], Verticillium Verticilium [for example Verticillium dahliae];

Cancer, galls and leaf cluster diseases caused by the following, such as Nectria [such as Nectria galligena];

Fusarium wilt caused by, for example, Monilinia [such as Monilinia laxa];

Deformation of leaves, flowers, and fruits caused by the following, such as Exobasidium (Exobasidium) [e.g. Exobasidium vexans, Taphrina (e.g. Taphrina deformans) ];

Degenerative diseases of woody plants caused by: for example, Esca (e.g. Phaemoniella clamydospora, Phaeoacremonium aleophilum) or Fomitiporia mediterranea )], Ganoderma [such as Ganoderma boninense];

Flower and seed diseases caused by eg Botrytis [eg Botrytis cinerea];

Diseases of plant tubers caused by the following, such as Rhizoctonia [e.g. Rhizoctonia solani], Helminthosporium [e.g. Helminthosporium solani )];

Diseases caused by bacterial pathogens, such as Xanthomonas [such as Xanthomonas campestris pv. Oryzae], Pseudomonas [such as Pseudomonas syringae cucumber Pathogenic species (Pseudomonas syringae pv. Lachrymans)], Erwinia (Erwinia) [for example, Erwinia amylovora].

In particular, the compound of formula (I) and the composition containing them can effectively control phytopathogenic fungi that cause rust. Seed treatment

Methods for controlling unwanted microorganisms can be used to protect seeds from phytopathogenic microorganisms, such as fungi.

The term "seed" as used herein includes dormant seeds, osmotic seeds, pre-germinated seeds and seeds with growing roots and leaves.

Therefore, the present invention also relates to a method for protecting seeds and/or crops from unwanted microorganisms, such as bacteria or fungi, which method includes treating seeds with one or more compounds of formula (I) or a composition comprising them的步。 The steps. Treating seeds with a compound of formula (I) or a composition containing them not only protects the seeds from phytopathogenic microorganisms, but also protects germinating plants, sprouting plants and post-emergence plants.

Seed treatment can be carried out before sowing, during sowing or immediately after sowing.

When the seed treatment is carried out before sowing (for example, the so-called application on the seed), the seed treatment can be carried out as follows: the seed and the desired amount of the compound of formula (I) or a composition containing them can be placed in a mixer , Mix the seed with the compound of formula (I) or the composition containing them (directly or after dilution) until a uniform distribution on the seed is achieved. If appropriate, the seeds can then be dried.

The present invention also relates to seeds treated with one or more compounds of formula (I) or compositions containing them. As mentioned above, the use of treated seeds not only protects the seeds from undesirable microorganisms, such as phytopathogenic fungi, before and after sowing, but also protects germinating plants and seedlings that grow from the treated seeds. Most of the damage caused by pests is caused by the infection of seeds before sowing or after the plants have germinated. This stage is particularly important because the roots and shoots of growing plants are particularly sensitive, and even small damage may cause plant death.

Therefore, the present invention also relates to methods for protecting seeds, germinating plants and sprouting plants, and more generally, to methods for protecting crops from pathogenic microorganisms, which include the use of one or more formulas ( I) The step of treating seeds with compounds or compositions containing them.

Preferably, the seed is treated in a state in which it is stable enough so that no damage occurs during the treatment. In general, the seed can be treated at any time between harvest and after sowing. Usually, seeds are used that have been separated from the plant and removed the cobs, shells, stems, skins, hairs or pulp of the fruit. For example, seeds that have been harvested, cleaned, and dried to a humidity below 15% by weight can be used. Another option is to use dried seeds, such as water-treated and then dried seeds or osmotic seeds, or seeds stored in osmotic conditions or pre-germinated seeds or sown on nursery trays, nursery belts or nursery papers seed.

The amount of the compound of formula (I) or the composition containing them applied to the seed is typically not harmful to the germination of the seed, or harmless to the resulting plant. This item must be kept in mind when the active ingredient may have a phytotoxic effect at a specific application rate. When deciding the amount of the compound of formula (I) or the composition containing them to be applied to the seed, the inherent phenotype of the transgenic plant should also be taken into consideration, so that the smallest compound of formula (I) or the amount of the composition containing them should be taken into consideration. The use of other components to achieve the best seed and budding plant protection.

As shown above, the compound of formula (I) can be applied directly to the seed, that is, without any other components and undiluted, or a composition containing the compound of formula (I) can be applied. Preferably, the composition is applied in any suitable form. Examples of suitable formulations include solutions, emulsions, suspensions, powders, foams, slurries, or combinations with other film coating compositions for seeds, such as film-forming materials, granulated materials, fine powdered iron or other metal powders, Granules, coating materials for inactivated seeds, and ULV formulations. The formulation may be a ready-to-use formulation or may be a concentrate that needs to be diluted before use.

These formulations are prepared in a known manner, for example, by combining the active ingredients or their mixtures with customary additives, such as customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, Antifoaming agent, preservative, second thickening agent, adhesive, gembesin and water are mixed.

These formulations are in a known manner by combining active ingredients or active ingredient mixtures with customary additives, such as customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers Preparation, preservative, second thickener, adhesive, gembein and water.

Useful dyes that can be present in seed dressing formulations are all dyes that are customary for this purpose. Pigments that are hardly soluble in water or dyes that are soluble in water can be used. Examples include the known dyes named Rhodamin B, C.I. Pigment Red 112 and C.I. Solvent Red 1. Useful wetting agents that can be present in seed dressing formulations are all substances that increase the degree of wetness and are used in formulations of active agrochemical ingredients. It is preferable to use alkyl naphthalene sulfonate, such as diisopropyl naphthalene sulfonate or diisobutyl naphthalene sulfonate. The useful dispersants and/or emulsifiers that may be present in the seed dressing formulations are all nonionic, anionic and cationic dispersants customarily used in formulations of active agrochemical ingredients. Preferably used are nonionic or anionic dispersants, or mixtures of nonionic or anionic dispersants. Useful nonionic dispersants include, in particular, ethylene oxide/propylene oxide block polymers, alkylphenol polyethylene glycol ethers and tristyrylphenol polyethylene glycol ethers and their phosphorylated or sulfated derivatives. Suitable anionic dispersants are, in particular, lignosulfonates, polyacrylates and arylsulfonate/formaldehyde condensates. The defoamers that can be present in the seed dressing formulations are all foam inhibitors commonly used in formulations of agrochemical active ingredients. Preferably, a silicone defoamer and magnesium stearate can be used. Preservatives that may be present in seed dressing formulations are all substances that can be used in agricultural chemical compositions for this purpose. Examples include dichlorophenol and benzyl alcohol hemiformal. The second thickener that may be present in the seed dressing formulation is all substances that can be used in agrochemical compositions for this purpose. Preferred examples include cellulose derivatives, acrylic acid derivatives, sanxian gum, modified clay, and fine powdered silica. The adhesives that can be present in seed dressing formulations are all conventional adhesives that can be used in seed dressing products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

The compound of formula (I) and the composition containing them are suitable for protecting the seeds of various plants used in any agriculture, greenhouse, forest or horticulture. More specifically, the seeds are grains (such as wheat, barley, rye, millet, triticale, and oats), rape, corn, cotton, soybeans, rice, potatoes, sunflowers, kidney beans, coffee, bowl beans, beets ( For example, sugar beet and fodder beet), peanuts, vegetables (such as tomatoes, cucumbers, onions and lettuce), turf and seeds of ornamental plants. Of particular importance is the treatment of seeds of wheat, soybeans, rapeseed, corn and rice.

The compound of formula (I) or the composition containing them can be used to treat genetically transformed seeds, in particular, plant seeds that can express proteins that are used to combat pests, herbicide damage or abiotic stress, thereby increasing the protective effect . Synergistic effects may also occur in the interaction with substances formed by performance. Apply

The compound of formula (I) can be applied directly or, for example, as ready-to-use solutions, emulsions, water-based and oil-based suspensions, powders, wettable powders, pastes, soluble powders, dusts, soluble granules, granules for cloth application , Concentrated suspension emulsions, natural products injected with the compound of formula (I), synthetic materials injected with the compound of formula (I), fertilizer or microencapsulated in polymers to be applied.

The application is carried out in a customary way, such as by pouring, spraying, spraying, broadcasting, dusting, foaming, spreading on it, etc. The compound of formula (I) can also be deployed by the ultra-low volume method via drip irrigation system or sprinkler irrigation, applied to furrows or injected into the soil, stems or branches. In addition, the compound of formula (I) can also be applied by wound sealing, coating or other wound dressings.

The effective and plant-compatible amount of the compound of formula (I) applied to plants, plant parts, fruits, seeds or soil will depend on various factors, such as the compound/composition used, and the treatment target (plant, plant part) , Fruit, seed or soil), treatment type (sprinkling powder, spraying, seed dressing), treatment purpose (therapeutic and protective), microorganism type, microorganism development stage, microorganism sensitivity, crop growth stage and environmental conditions.

When the compound of formula (I) is used as a fungicide, the application rate can vary within a fairly wide range according to the kind of application. For the treatment of plant parts, such as leaves, the application rate can range from 0.1 to 10000 g/ha, preferably 10 to 1000 g/ha, and more preferably 50 to 300 g/ha (when applied by sprinkling or dripping In this case, it is even possible to reduce the application rate, especially when using inert materials such as rock wool or nacre). For seed treatment, the application rate can range from 0.1 to 200 g per 100 kg of seeds, preferably 1 to 150 g per 100 kg of seeds, more preferably 2.5 to 25 g per 100 kg of seeds, and even more preferably per 100 kg of seeds. 100 kg of seeds 2.5 to 12.5 g. For the treatment of soil, the application rate can range from 0.1 to 10000 g/ha, preferably 1 to 5000 g/ha.

These application rates are only examples and are not intended to limit the scope of the invention. Material protection

The compounds and compositions of the present invention can also be used for material protection, especially for protecting industrial materials against the attack and destruction of unwanted microorganisms.

In addition, the compounds and compositions of the present invention can be used alone or in combination with other active ingredients as antifouling compositions.

In the context of the present invention, industrial materials should be understood to refer to inanimate substances prepared for industrial use. For example, industrial materials that can be protected from microbial alteration or destruction can be adhesives, glues, paper, wallpaper and board/cardboard, textiles, carpets, leather, wood, fibers and paper towels, paint and plastic items, cooling lubricants And other substances that can be infected or destroyed by microorganisms. In the scope of materials that can be protected, parts of production plants and buildings can also be mentioned, such as cooling water circuits, cooling and heating systems, and ventilation and air conditioning components that may be harmed by microbial proliferation. The industrial materials within the scope of the present invention preferably include adhesives, glues, paper and plates, leather, wood, paint, cooling lubricants and heat transfer fluids, and more preferably wood.

The compounds and compositions of the present invention can prevent adverse effects such as spoilage, decay, discoloration, fading, or mold.

In the case of wood treatment, the compounds and compositions of the present invention can also be used to combat fungal diseases that tend to grow on or inside wood.

Timber refers to all types of wood materials, and all types of wood processing intended for construction, such as solid wood, high-density wood, laminated wood, and plywood. In addition, the compounds and compositions of the present invention can be used to protect objects in contact with seawater or salt water, especially ship hulls, screens, nets, buildings, breakwaters and signal transmission systems, to avoid fouling.

The compounds and compositions of the present invention can also be used to protect stored items. Stored items should be understood to refer to natural materials or processed products of plant or animal origin of natural origin, and the items are intended to be protected for a long time. Storage items of plant origin, such as plants or plant parts such as stems, leaves, tubers, seeds, fruits, and grains can be just harvested or after (pre-)drying, humidification, division, milling, pressing or baking treatments Give protection. Storage items also include unprocessed wood such as construction wood, telephone poles and fences, or finished wood such as furniture. Storage items of animal origin include raw hides, leather, feathers and hair. The compounds and compositions of the present invention can prevent adverse effects such as spoilage, decay, discoloration, fading, or mold.

Microorganisms that can degrade or change industrial materials include, for example, bacteria, fungi, yeasts, algae, and slime organisms. Compounds and compositions of the present invention are preferably used against fungal-based, in particular molds, wood - and wood discoloration --destroying fungi (ascomycetes (Ascomycetes), Basidiomycetes (Basidiomycetes), incomplete fungi (, Deuteromycetes) and zygomycete ( Zygomycetes )), and against slime organisms and algae. Examples include microorganisms of the following genera: Alternaria , such as Alternaria tenuis ; Aspergillus , such as Aspergillus niger ; Chaetomium , such as globularia Chaetomium globosum ; Coniophora , such as Coniophora puetana ; Lentinus , such as Lentinus tigrinus ; Penicillium , such as gray-green Penicillium glaucum ; Polyporus , such as Polyporus versicolor ; Aureobasidium , such as Aureobasidium pullulans ; Sclerophoma , such as Sclerophoma pityophila; Trichoderma (Trichoderma), for example, Trichoderma viride (Trichoderma virid e); (. Ophiostoma spp) (. Ceratocystis spp) (. Humicola spp) belongs to the nozzle housing, long flavor shell genus Humicola, Petriella spp . , Trichurus spp.; Coriolus spp., Gloeophyllum spp., Pleurotus spp., Pleurotus spp. Genus ( Poria spp.), Serpula spp. and Tyromyces spp., Cladosporium spp., Paecilomyces spp., Mucor spp), Bacillus (Escherichia), such as E. coli (Escherichia coli);. Pseudomonas (Pseudomonas), for example, Pseudomonas aeruginosa (Pseudomonas aeruginosa); Staphylococcus (Staphylococcus), such as Staphylococcus aureus (Staphylococcus aureus ), Candida spp and Saccharomy ces spp), such as Saccharomyces cerevisae .

Refer to the following examples to further understand the state of this teaching, which should not be construed as limiting the scope of this teaching in any way. Instance

The following examples illustrate the preparation and utility of the compounds of formula (I) according to the present invention in a non-limiting manner. Synthesis of intermediate 4,4,4-trifluoro-1-[4-(1H-imidazol-1-yl)phenyl]butan-1,3-dione of formula (II) according to method P1

To a solution of 1-[4-(1H-imidazol-1-yl)phenyl]ethanone (200 mg, 1.1 mmol) dissolved in THF (2.8 mL) was added 2,2,2-trifluoroethyl acetate ( 305 mg, 2.2 mmol) and then add potassium tert-butoxide (2.2 mL, 2.2 mmol, 1 M solution in THF) dropwise at 0°C. The mixture was stirred at rt for 1 h. Then add aqueous hydrochloric acid (2.2 mL, 1 M). The aqueous layer was extracted with ethyl acetate. The combined organic layer was dried (MgSO ₄ ), filtered and concentrated under reduced pressure to obtain the title compound (262 mg, 80% purity, 69% yield), which was used in the next step without further purification. Synthetic formula (V) intermediate 1-(4-bromo-2-fluorophenyl)-4,4,4-trifluorobutane-1,3-dione

A solution of 4-bromo-2-fluoroacetophenone (25 g, 1 eq) and sodium hydride (5.99 g, 1.3 eq, 60%) in degassed THF (200 mL) was stirred at 0°C for 30 min . Add 2,2,2-trifluoroethyl acetate (21.3 g, 1.3 eq) in portions at 0°C within 5 min. The mixture was stirred at rt for 3 h. Then add water and ice (400 ml). The aqueous layer was extracted 3 times with ethyl acetate. The combined organic layer was dried (MgSO ₄ ), filtered and concentrated under reduced pressure to obtain the title compound (25 g), which was used in the next step without further purification. 3-(4-Bromo-2-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol

Add hydroxylamine hydrochloride (3.68 g, 1.2 eq) to 1-(4-bromo-2-fluorophenyl)-4,4,4-trifluorobutan-1,3-dione (20 g, 1 eq) dissolved in acetic acid (100 mL) solution. The mixture was stirred at 120°C for 3 h. Add ice-water mixture (300 mL) at rt. The aqueous layer was extracted 3 times with ethyl acetate. The combined organic layers were dried (Na ₂ SO ₄ ), filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography to obtain the title compound (10.4 g, 50% yield) as an off-white solid. MS (ESI): 328 ([M+H] ⁺ ) Synthesis of intermediate (VII) according to method P6 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxa Boropentan-2-yl)phenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol

Combine 3-(4-bromophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol (100 mg, 0.32 mmol), double (pinacol Compound) diboron (123 mg, 0.48 mmol), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II), dichloromethane complex (7.3 mg, 0.011 mmol) and acetic acid Potassium (95 mg, 0.97 mmol) was dissolved in degassed dioxane (2 ml). The mixture was stirred at 80°C for 3 h and then cooled to rt and diluted with water and ethyl acetate. The layers were separated and the aqueous phase was extracted twice with ethyl acetate. The organic layers were combined, dried with MgSO ₄ and concentrated under reduced pressure. The residue was purified by flash chromatography (eluent: heptane/ethyl acetate) to obtain the title compound (95 mg, 78% yield) as a pale yellow honey. MS (ESI): 358 ([ M + H] +) Synthesis of compounds of formula I 3- [4- (1H- imidazol-1-yl) phenyl] -5- (trifluoromethyl) -4,5- Hydrogen -1,2- oxazol- 5- ol ( Compound I-034)

Add hydroxylamine hydrochloride (72 mg, 1.03 mmol) to 4,4,4-trifluoro-1-[4-(1H-imidazol-1-yl)phenyl]butan-1,3-dione ( 261 mg, 0.74 mmol) dissolved in acetic acid (2.5 mL). The mixture was stirred at 100°C for 1 h. Then pour it into water and stir for 15 min. The solid was filtered and dried to obtain the title compound (103 mg, 46% yield). MS (ESI): 298 ([M+H] ⁺ ) 3-[4-(1- ethyl -1H- pyrazol- 4 -yl ) phenyl )-5-( trifluoromethyl )-4,5 - 1,2-dihydro-5-ol 㗁

In 1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (86 mg, 0.39 mmol) Hesi (triphenylphosphine) palladium(0) (20 mg, 0.018 mmol) was added to an aqueous solution (1 ml) of cesium carbonate (125 mg, 0.39 mmol) and 3-(4-bromophenyl)-5-( A solution of trifluoromethyl-4,5-dihydro-1,2-oxazol-5-ol (108 mg, 0.35 mmol) in 1,2-dimethoxyethane (3 ml). The mixture was stirred at 80°C for 1 h and then cooled to rt. Then water and dichloromethane were added and separated into 2 layers. The organic layer was filtered with a silica gel filter, dissolved in dichloromethane and evaporated. The residue was purified using preparative HPLC-MS (SunFire Waters, 30*150, 5 µm, eluent: acetonitrile/water (0.1% formic acid)) to obtain the title compound (25.7 mg, 23% yield). MS (ESI): 324 ([M+H] ⁺ ) (5S)-3-[4-(1- ethyl -1H- pyrazol- 4 -yl ) phenyl )-5-( trifluoromethyl ) -4,5 -Dihydro -1,2- oxazol- 5- yl acetate and (5R)-3-[4-(1- ethyl -1H- pyrazol- 4 -yl ) phenyl ]- 5-( Trifluoromethyl )-4,5 -dihydro -1,2- oxazol- 5- yl acetate ( compounds I-026 and I-041)

Add 3-[4-(1-ethyl-1H-pyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole-5- A mixture of alcohol (100 mg, 0.31 mmol), acetic anhydride (471 mg, 4.6 mmol) and N,N-dimethylaminopyridine (75 mg, 0.62 mmol) dissolved in acetic acid (2 mL) was stirred at 70°C 6 h. The solvent was evaporated and the residue was dissolved in ethyl acetate, washed with water, dried with magnesium sulfate and evaporated. The residue was purified by flash chromatography to give racemic 3-[4-(1-ethyl-1H-pyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5- Dihydro-1,2-oxazol-5-yl acetate (100 mg, 88% yield). Separate the enantiomers by SFC (solvent: CO ₂ /acetonitrile) with a palm mirror to obtain: Isomer 1 : (5S)-3-[4-(1- ethyl -1H- pyrazole- 4-) yl) phenyl] -5- (trifluoromethyl) -4,5-dihydro-1,2-㗁-5-yl acetate or (5R) -3- [4- (1- ethyl- -1H- pyrazol- 4 -yl ) phenyl )-5-( trifluoromethyl )-4,5 -dihydro -1,2- oxazol- 5- yl acetate ( compound I-026) MS (ESI): 368 ([M+H]+) Optical rotation: +109,6° (c=0,68, MeOH, 25°C, 589 nm) Isomer 2 : (5S)-3-[4 -(1- Ethyl -1H- pyrazol- 4 -yl ) phenyl )-5-( trifluoromethyl )-4,5 -dihydro -1,2- oxazol- 5- yl acetate or (5R)-3-[4-(1- ethyl -1H- pyrazol- 4 -yl ) phenyl )-5-( trifluoromethyl )-4,5 -dihydro -1,2 -oxazole -5- yl acetate ( Compound I-041) MS (ESI): 368 ([M+H] ⁺ ) Optical rotation: -109,6° (c=0,68, MeOH, 25°C, 589 nm ) 3-[4-(1- ethyl -1H- pyrazol- 4 -yl )-2- fluorophenyl ]-5-( trifluoromethyl )-4,5 -dihydro -1,2- 㗁Azol- 5- ol ( Compound I-042)

Add 1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (75 mg, 0.35 mmol) , 3-(4-Bromo-2-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol (100 mg, 0.31 mmol), [ 1,1-bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) (9.9 mg, 0.015 mmol) and cesium carbonate (109 mg, 0.34 mmol) dissolved in degassed dioxane (1.5 ml) and dissolved in degassed water (0.5 ml). The mixture was stirred at 80°C for 90 min and then cooled to rt and diluted with water and ethyl acetate. The layers were separated and the aqueous phase was extracted twice with ethyl acetate. The organic layers were combined, dried with MgSO ₄ and concentrated under reduced pressure. The residue was purified by flash chromatography (eluent: heptane/ethyl acetate) to obtain the title compound (69 mg, 63% yield) as a white solid. MS (ESI): 344 ([M+H] ⁺ ) 3-[4-[5-( difluoromethyl )-1,2,4 -oxadiazol- 3 -yl ] phenyl )-5-( Trifluoromethyl )-4H-1,2- oxazol- 5- ol ( Compound I-049)

To a solution of 4-acetylbenzonitrile (1.0 g, 6.88 mmol) dissolved in 30 ml THF at 0°C was added sodium hydride (330 mg, 8.26 mmol, 60% dissolved in oil) in portions. The reaction was stirred for 30 min and then ethyl trifluoroacetate (1.64 ml, 13.7 mmol) was added. The mixture was stirred for 1 h and then water was added. The mixture was extracted 3 times with ethyl acetate, washed with brine, dried with MgSO ₄ and evaporated to give 4-(4,4,4-trifluoro-3-oxobutyryl)benzonitrile (1.7 g, 91% yield ) Is a mixture of diketone and ketoenol, which is used in the next step without further purification.

To a suspension of 4-(4,4,4-trifluoro-3-oxobutyryl)benzonitrile (1.7 g, 7.0 mmol) dissolved in acetic acid (25 ml) was added hydroxylamine hydrochloride (508 mg, 7.3 mmol). The mixture was stirred at 50°C for 2h. Then hydroxylamine hydrochloride (100 mg) was added and the mixture was stirred for another 4 h at 50°C. The reaction mixture was cooled to RT, poured into ice/water and stirred for 30 min. The precipitate was filtered out, washed with water and dried in vacuum to obtain 4-{5-[trifluoromethyl]-5-hydroxy-4,5-dihydro-1,2-oxazol-3-yl}benzyl Nitrile (1.6 g, 85% yield), used in the next step without further purification.

In 4-{5-[trifluoromethyl]-5-hydroxy-4,5-dihydro-1,2-oxazol-3-yl}benzonitrile (550 mg, 2.14 mmol) and hydroxylamine hydrochloride Sodium carbonate (455 mg, 4.3 mmol) was added to the mixture of salt (298 mg, 4.3 mmol) dissolved in methanol (10 ml). The mixture was refluxed for 8 h. Then the solvent was evaporated and the residue was dissolved in ethyl acetate, washed with water, dried with MgSO ₄ and evaporated to obtain N'-hydroxy-4-[5-hydroxy-5-(trifluoromethyl)-4,5- Dihydro-1,2-oxazol-3-yl]benzamidine (396 mg, 54% yield, 85% purity) was a creamy solid, which was used in the next step without further purification.

N'-hydroxy-4-[5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]benzamidine (250 mg, 0.86 mmol) The mixture dissolved in ethyl difluoroacetate (1.5 ml) was stirred at 100°C overnight. The solvent was concentrated under reduced pressure and the residue was purified by preparative HPLC (eluent: acetonitrile/water (0.1% formic acid)) to obtain the title compound (110 mg, 36%) as a brown solid. MS (ESI): 350 ([M+H] ⁺ ) 3-[4-(5 -methyl -1,3,4 -oxadiazol- 2- yl ) phenyl )-5-( trifluoromethyl )-4H-1,2- oxazol- 5- ol ( Compound I-053)

To the suspension of methyl 4-acetylbenzoate (15 g, 84,1 mmol) dissolved in 250 ml of ether, ethyl trifluoroacetate (13 g, 92.6 mmol) was added dropwise and sodium methoxide 0,5M A solution dissolved in MeOH (202 ml, 101 mmol). The mixture was stirred at rt for 24 h and then HCl 1M (130 ml) was added. The mixture was extracted 3 times with ether, dried with MgSO ₄ and evaporated to obtain methyl 4-(4,4,4-trifluoro-3-oxobutyryl)benzoate (20.8 g, 74% yield, 82% purity) It is a mixture of diketone and ketoenol and used in the next step without further purification. MS (ESI): 275 ([M+H]+)

To a mixture of methyl 4-(4,4,4-trifluoro-3-oxobutyryl)benzoate (8 g, 20.7 mmol) in acetic acid (50 ml) was added hydroxylamine hydrochloride (1.66 g, 23.8 mmol). The mixture was stirred at 80°C for 1.5 h. The reaction mixture was cooled to RT, poured into water (400 ml) and stirred for 15 min. The precipitate was filtered off, washed with heptane and dried to obtain methyl 4-{5-trifluoromethyl-5-hydroxy-4,5-dihydro-1,2-oxazol-3-yl}benzoate ( 6.2 g, 97% yield) is a beige solid. MS (ESI): 290 ([M+H] ⁺ )

In 4-{5-trifluoromethyl-5-hydroxy-4,5-dihydro-1,2-oxazol-3-yl}benzoic acid methyl ester (5.2 g, 17.8 mmol) dissolved in methanol (40 ml Add water (5 ml) and sodium hydroxide (1.5 g, 35.7 mmol) to the mixture. The mixture was stirred at 60°C for 1.5 h. The mixture was poured into a mixture of cold HCl 1M (100ml) and water (100ml) and stirred for 5 min. The precipitate was filtered and dried to obtain 4-{5-trifluoromethyl-5-hydroxy-4,5-dihydro-1,2-oxazol-3-yl}benzoic acid (3.8 g, 74% yield ) Is a beige solid. MS (ESI): 276 ([M+H] ⁺ )

In 4-{5-trifluoromethyl-5-hydroxy-4,5-dihydro-1,2-oxazol-3-yl}benzoic acid (1.0 g, 3.63 mmol), acethydrazine (151 mg, 2.03 mmol), 1-hydroxybenzotriazole (49 mg, 0.63 mmol) and EDCI (390 mg, 2.03 mmol) dissolved in DMF (7 ml) were added TEA (0.28 ml, 2.03 mmol). The mixture was stirred at RT overnight and diluted with ethyl acetate. Then add water. The layers were separated and the aqueous phase was extracted twice with ethyl acetate. The organic layers were combined, washed with brine, dried over MgSO ₄ and concentrated under reduced pressure. The residue was purified by preparative HPLC (eluent: acetonitrile/water (0.1% formic acid)) to obtain N'-acetyl-4-[5-hydroxy-5-(trifluoromethyl)-4,5 -Dihydro-1,2-oxazol-3-yl]benzylhydrazine. MS (ESI): 332 ([M+H] ⁺ )

The N'-acetyl-4-[5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]benzylhydrazine (313 mg, A mixture of 0.94 mmol) dissolved in phosphorus oxychloride (2.6 ml, 28.3 mmol) was stirred in a microwave at 60°C for 4 h, cooled to rt and diluted with toluene. Then the solvent is evaporated. The residue was diluted with water and the precipitate was purified by preparative HPLC (eluent: acetonitrile/water (0.1% formic acid)) to obtain the title compound (84 mg, 27% yield). MS (ESI): 314 ([M+H] ⁺ ) 3-[4-(1,2- thiazol- 4 -yl ) phenyl ]-5-( trifluoromethyl )-4H-1,2- 㗁Azol- 5- ol ( Compound I-068)

Add 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(trifluoromethyl)-4 , 5-Dihydro-1,2-oxazol-5-ol (144 mg, 0.40 mmol), 4-bromoisothiazole (73 mg, 0.44 mmol), [1,1-bis(di-tertiary butyl) Phosphonyl)ferrocene)dichloropalladium(II) (13 mg, 0.02 mmol) and cesium carbonate (130 mg, 0.40 mmol) dissolved in degassed dioxane (1.5 ml) and degassed water (0.5 ml) )in. The mixture was stirred at 90°C for 1 h and then cooled to rt and concentrated under reduced pressure. The residue was dissolved in DCM, filtered with a silica gel filter, evaporated and purified by preparative HPLC-MS (eluent: acetonitrile/water (0.1% formic acid)) to obtain the title compound (61 mg, 48% yield). MS (ESI): 315 ([M+H] ⁺ )

(I) 實例編號 X R1 (F)_m

LogP 立體 異構物 I.001 F H  - 1-(2-乙氧基-2-側氧乙基)-1H-吡唑-4-基 2.54^[a]   I.002 F H  - 5-乙醯基-2-噻吩基 2.92^[a]   I.003 F H  - 3-噻吩基 3.25^[a]   I.004 F H  - 1-(4-氟苯基)-1H-吡唑-4-基 3.53^[a]   I.005 Cl H  - 1-乙基-1H-吡唑-4-基 2.57^[a]   I.006 F H  - 4-甲基-2-噻吩基 3.74^[a]   I.007 F H  - 1-(2-甲基丙基)-1H-吡唑-4-基 3.06^[a]   I.008 F H  - 4-苯基-1,3-噻唑-2-基 4.15^[a]   I.009 F H  - 噻吩-2-基 3.31^[a]   I.010 F H  - 1-甲基-1H-吡咯-3-基 2.92^[a]   I.011 F H  - 1-(二氟甲基)-1H-吡唑-4-基 2.70^[a]   I.012 F H  - 1,3,5-三甲基-1H-吡唑-4-基 2.28^[a]   I.013 F H  - 1-異丙基-1H-吡唑-4-基 2.77^[a]   I.014 F H  - 5-苯基-2-噻吩基 4.55^[a]   I.015 F H  - 5-甲醯基-2-噻吩基 2.80^[a]   I.016 F H  - 1-甲基-3-(三氟甲基)-1H-吡唑-4-基 3.00^[a]   I.017 F H 3-F 1-乙基-1H-吡唑-4-基 2.67^[a]   I.018 F H  - 5-(嗎福啉-4-基甲基)-2-噻吩基 1.52^[a]   I.019 F H  - 3-甲氧基-2-噻吩基 3.37^[a]   I.020 F H  - 5-異丙基-1,3-噻唑-2-基 3.69^[a]   I.021 F H  - 呋喃-3-基 2.92^[a]   I.022 F H 2-F 1-甲基-1H-吡唑-4-基 2.28^[a]   I.023 Cl H  - 1,2-㗁唑-4-基 2.49^[a]   I.024 F H  - 1-苯甲基-1H-吡唑-4-基 3.13^[a]   I.025 F H  - 1-(2-甲氧基乙基)-1H-吡唑-4-基 2.26^[a]   I.026 F 乙醯基  - 1-乙基-1H-吡唑-4-基 3.15^[a] 異構物1 I.027 F H  - 1-丙基-1H-吡唑-4-基 2.75^[a]   I.028 F H  - 1-(羧甲基)-1H-吡唑-4-基 1.82^[a]   I.029 F H  - 5-甲基-2-呋喃基 3.44^[a]   I.030 Cl H  - 1-甲基-1H-吡唑-4-基 2.23^[a]   I.031 F H  - 1-(第三丁氧基羰基)-1H-吡唑-4-基 3.15^[a]   I.032 F H  - 1,3-二甲基-1H-吡唑-4-基 2.23^[a]   I.033 F H  - 1-環戊基-1H-吡唑-4-基 2.23^[a]   I.034 F H  - 1H-咪唑-1-基 0.93^[a]   I.035 F H  - 1-苯基-1H-吡唑-4-基 3.47^[a]   I.036 F H  - 1-(噻吩-2-基甲基)-1H-吡唑-4-基 2.95^[a]   I.037 F H  - 3-甲基-1,2-㗁唑-5-基 2.62^[a]   I.038 F H  - 1-乙基-1H-三唑-4-基 2.16^[a]   I.039 F H 2-F 1,2-㗁唑-4-基 2.51^[a]   I.040 F 2-甲氧基乙醯基  - 1-乙基-1H-吡唑-4-基 3.06^[a]   I.041 F 乙醯基  - 1-乙基-1H-吡唑-4-基 3.15^[a] 異構物2 I.042 F H 2-F 1-乙基-1H-吡唑-4-基 2.62^[a]   I.043 F H  - 2-氯-3-噻吩基 3.71^[a]   I.044 F H  - 5-氰基-2-噻吩基 3.13^[a]   I.045 F H  - 1-甲基-1H-吡咯-2-基 3.07^[a]   I.046 F H  - 5-環戊基-1,2,4-㗁二唑-3-基 3.91^[a]   I.047 F H  - 5-(2,4-二氟苯基)-1,2,4-㗁二唑-3-基 3.88^[a]   I.048 F H  - 5-(2,4-二氟苯基)-1,3,4-㗁二唑-2-基 3.19^[a]   I.049 F H  - 5-(二氟甲基)-1,2,4-㗁二唑-3-基 2.94^[a]   I.050 F H  - 5-環戊基-1,3,4-㗁二唑-2-基 3.07^[a]   I.051 F H  - 5-甲基-1,2,4-㗁二唑-3-基 2.49^[a]   I.052 F H  - 5-(2-氯苯基)-1,3,4-㗁二唑-2-基 3.40^[a]   I.053 F H  - 5-甲基-1,3,4-㗁二唑-2-基 2.01^[a]   I.054 F H  - 5-(二氟甲基)-1,3,4-㗁二唑-2-基 2.54^[a]   I.055 F H  - 5-第三丁基-1,3,4-噻二唑-2-基 3.28^[a]   I.056 F H  - 1-第三丁基-1H-吡唑-4-基 3.06^[a]   I.057 F H  - 1-烯丙基-1H-咪唑-5-基 1.29^[a]   I.058 F H  - 5-(三氟甲基)-1,3,4-㗁二唑-2-基 3.08^[a]   I.059 F H  - 5-(三氟甲基)-1,2,4-㗁二唑-3-基 3.81^[a]   I.060 F H  - 1-吡啶-2-基-1H-吡唑-3-基 3.50^[a]   I.061 F H  - 2-甲醯基-3-噻吩基 2.78^[a]   I.062 F H  - 5-甲醯基-3-噻吩基 2.80^[a]   I.063 F H  - 2-甲醯基-5-甲基-3-噻吩基 3.09^[a]   I.064 F H  - 3-甲基-1,2,4-㗁二唑-5-基 2.54^[a]   I.065 F H  - 5-第三丁基-1,3,4-㗁二唑-2-基 2.90^[a]   I.066 F H  - 1,3-噻唑-5-基 2.31^[a]   I.067 F H  - 異噻唑-5-基 2.64^[a]   I.068 F H  - 異噻唑-4-基 2.55^[a]   I.069 F H  - 5-環丙基-1,3,4-㗁二唑-2-基 2.46^[a]   I.070 F H  - 1-(環丙基甲基)-1H-吡唑-4-基 2.86^[a]   I.071 F H  - 1-環丙基-1H-吡唑-4-基 2.54^[a]   Similar to the examples provided above, the compounds in Table 1 were prepared. Table 1: Compounds according to formula (I)

(I) Instance number X R1 (F) _m

LogP Stereoisomer I.001 F H - 1-(2-Ethoxy-2-oxoethyl)-1H-pyrazol-4-yl 2.54 ^[a] I.002 F H - 5-Acetyl-2-thienyl 2.92 ^[a] I.003 F H - 3-thienyl 3.25 ^[a] I.004 F H - 1-(4-Fluorophenyl)-1H-pyrazol-4-yl 3.53 ^[a] I.005 Cl H - 1-Ethyl-1H-pyrazol-4-yl 2.57 ^[a] I.006 F H - 4-methyl-2-thienyl 3.74 ^[a] I.007 F H - 1-(2-methylpropyl)-1H-pyrazol-4-yl 3.06 ^[a] I.008 F H - 4-phenyl-1,3-thiazol-2-yl 4.15 ^[a] I.009 F H - Thiophen-2-yl 3.31 ^[a] I.010 F H - 1-methyl-1H-pyrrol-3-yl 2.92 ^[a] I.011 F H - 1-(Difluoromethyl)-1H-pyrazol-4-yl 2.70 ^[a] I.012 F H - 1,3,5-Trimethyl-1H-pyrazol-4-yl 2.28 ^[a] I.013 F H - 1-isopropyl-1H-pyrazol-4-yl 2.77 ^[a] I.014 F H - 5-phenyl-2-thienyl 4.55 ^[a] I.015 F H - 5-methanyl-2-thienyl 2.80 ^[a] I.016 F H - 1-Methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl 3.00 ^[a] I.017 F H 3-F 1-Ethyl-1H-pyrazol-4-yl 2.67 ^[a] I.018 F H - 5-(morpholin-4-ylmethyl)-2-thienyl 1.52 ^[a] I.019 F H - 3-methoxy-2-thienyl 3.37 ^[a] I.020 F H - 5-isopropyl-1,3-thiazol-2-yl 3.69 ^[a] I.021 F H - Furan-3-yl 2.92 ^[a] I.022 F H 2-F 1-methyl-1H-pyrazol-4-yl 2.28 ^[a] I.023 Cl H - 1,2-oxazol-4-yl 2.49 ^[a] I.024 F H - 1-Benzyl-1H-pyrazol-4-yl 3.13 ^[a] I.025 F H - 1-(2-Methoxyethyl)-1H-pyrazol-4-yl 2.26 ^[a] I.026 F Acetyl - 1-Ethyl-1H-pyrazol-4-yl 3.15 ^[a] Isomer 1 I.027 F H - 1-propyl-1H-pyrazol-4-yl 2.75 ^[a] I.028 F H - 1-(carboxymethyl)-1H-pyrazol-4-yl 1.82 ^[a] I.029 F H - 5-methyl-2-furyl 3.44 ^[a] I.030 Cl H - 1-methyl-1H-pyrazol-4-yl 2.23 ^[a] I.031 F H - 1-(Third-butoxycarbonyl)-1H-pyrazol-4-yl 3.15 ^[a] I.032 F H - 1,3-Dimethyl-1H-pyrazol-4-yl 2.23 ^[a] I.033 F H - 1-cyclopentyl-1H-pyrazol-4-yl 2.23 ^[a] I.034 F H - 1H-imidazol-1-yl 0.93 ^[a] I.035 F H - 1-Phenyl-1H-pyrazol-4-yl 3.47 ^[a] I.036 F H - 1-(Thien-2-ylmethyl)-1H-pyrazol-4-yl 2.95 ^[a] I.037 F H - 3-methyl-1,2-oxazol-5-yl 2.62 ^[a] I.038 F H - 1-ethyl-1H-triazol-4-yl 2.16 ^[a] I.039 F H 2-F 1,2-oxazol-4-yl 2.51 ^[a] I.040 F 2-Methoxy Acetyl - 1-Ethyl-1H-pyrazol-4-yl 3.06 ^[a] I.041 F Acetyl - 1-Ethyl-1H-pyrazol-4-yl 3.15 ^[a] Isomer 2 I.042 F H 2-F 1-Ethyl-1H-pyrazol-4-yl 2.62 ^[a] I.043 F H - 2-chloro-3-thienyl 3.71 ^[a] I.044 F H - 5-cyano-2-thienyl 3.13 ^[a] I.045 F H - 1-methyl-1H-pyrrol-2-yl 3.07 ^[a] I.046 F H - 5-cyclopentyl-1,2,4-diazol-3-yl 3.91 ^[a] I.047 F H - 5-(2,4-Difluorophenyl)-1,2,4-oxadiazol-3-yl 3.88 ^[a] I.048 F H - 5-(2,4-Difluorophenyl)-1,3,4-Diazol-2-yl 3.19 ^[a] I.049 F H - 5-(Difluoromethyl)-1,2,4-oxadiazol-3-yl 2.94 ^[a] I.050 F H - 5-cyclopentyl-1,3,4-diazol-2-yl 3.07 ^[a] I.051 F H - 5-methyl-1,2,4-oxadiazol-3-yl 2.49 ^[a] I.052 F H - 5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl 3.40 ^[a] I.053 F H - 5-methyl-1,3,4-oxadiazol-2-yl 2.01 ^[a] I.054 F H - 5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl 2.54 ^[a] I.055 F H - 5-tert-butyl-1,3,4-thiadiazol-2-yl 3.28 ^[a] I.056 F H - 1-tert-butyl-1H-pyrazol-4-yl 3.06 ^[a] I.057 F H - 1-allyl-1H-imidazol-5-yl 1.29 ^[a] I.058 F H - 5-(Trifluoromethyl)-1,3,4-oxadiazol-2-yl 3.08 ^[a] I.059 F H - 5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl 3.81 ^[a] I.060 F H - 1-Pyridin-2-yl-1H-pyrazol-3-yl 3.50 ^[a] I.061 F H - 2-methanyl-3-thienyl 2.78 ^[a] I.062 F H - 5-methanyl-3-thienyl 2.80 ^[a] I.063 F H - 2-methanyl-5-methyl-3-thienyl 3.09 ^[a] I.064 F H - 3-methyl-1,2,4-oxadiazol-5-yl 2.54 ^[a] I.065 F H - 5-tert-butyl-1,3,4-diazol-2-yl 2.90 ^[a] I.066 F H - 1,3-thiazol-5-yl 2.31 ^[a] I.067 F H - Isothiazol-5-yl 2.64 ^[a] I.068 F H - Isothiazol-4-yl 2.55 ^[a] I.069 F H - 5-cyclopropyl-1,3,4-oxadiazol-2-yl 2.46 ^[a] I.070 F H - 1-(Cyclopropylmethyl)-1H-pyrazol-4-yl 2.86 ^[a] I.071 F H - 1-cyclopropyl-1H-pyrazol-4-yl 2.54 ^[a]

The LogP value is measured by HPLC (High Performance Liquid Chromatography) on a reverse phase column in accordance with EEC Directive 79/831 Annex V.A8 by the following method:

^{[a] The} LogP value is measured by LC-UV, in the acid range, with 0.1% formic acid dissolved in water and acetonitrile as the eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).

^{[b] The} LogP value is measured by measuring LC-UV in the neutral range with a solution of ammonium acetate dissolved in water and acetonitrile at a concentration of 0.001 mol as the eluent (linear gradient from 10% acetonitrile to 95% Acetonitrile).

^{[c] The} LogP value is measured by measuring LC-UV in the acid range with 0.1% phosphoric acid and acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile).

If more than one LogP value is obtained in the same method, all values are provided and separated by "+".

Calibration is performed with linear alkane 2-ketones (with 3 to 16 carbon atoms) with known LogP values (using residence time to measure LogP values by linear interpolation between successive alkanones). Use 200 nm to 400 nm UV-spectrum and the peak value of the tomographic signal to determine the λ-max-value. NMR- peak list

The 1H-NMR data of the selected examples are written in the form of 1H-NMR-peak table. For each signal peak series, give the δ-value expressed in ppm and the signal intensity in parentheses. Paired δ-values-the signal strength is separated by a semicolon.

The peak table of the example therefore has the following form: δ ₁ (intensity ₁ ); δ ₂ (intensity ₂ ); .....; δ _i (intensity _i ); ...; δ _n (intensity _n )

In the example of a printed NMR spectrum (in cm), the sharp signal intensity is related to the height of the signal and shows the true relationship of the signal intensity. From the wide signal, it can display the peak or intermediate value and relative intensity of several signals compared with the strongest signal in the spectrum.

To calibrate the chemical shift of the 1H spectrum, we use tetramethylsilane and/or the chemical shift of the solvent used, especially in the case of the spectrum measured with DMSO. Therefore, in the NMR peak table, the peak of tetramethylsilane may occur, but it is not inevitable.

^{The 1} H-NMR peak table system is similar to the orthodox ¹ H-NMR chart and therefore usually contains all the peaks listed in the orthodox NMR-analysis chart.

In addition, it can display orthodox 1H-NMR spectrum signals such as solvents, stereoisomers of the target compound that is also the target of the present invention, and/or peaks of impurities.

As for the compound signal in the δ-range of the solvent and/or water, the usual solvent peaks, such as the DMSO peak in DMSO-D ₆ and the water peak are shown on the 1H-NMR peak list and usually have high averages. strength.

The peaks of the stereoisomers of the target compound and/or the peaks of impurities usually have an average lower than the peak intensity of the target compound (for example, having a purity of >90%).

These stereoisomers and/or impurities may be typical of specific preparation procedures. Therefore, its peaks can be identified through the "by-product fingerprint" to help identify the remanufacturing of the preparation process.

Professionals use known methods to calculate the peaks of the target compound (MestreC, ACD-simulation, but also the expected value estimated by experience), and use additional intensity filters as needed to separate the peaks of the target compound. This separation should be similar to the extraction of the relevant peaks in the ^{orthodox 1 H-NMR spectrum.}

For further details of the NMR-data description with the peak table, please refer to the publication "Citation of NMR Peaklist Data within Patent Applications" of Research Disclosure Database Number 564025. I.002: ¹ H-NMR(400.2 MHz, d ₆ -DMSO): δ= 8.6983 (4.2); 7.9904 (2.9); 7.9806 (3.0); 7.9539 (1.8); 7.9081 (3.2); 7.8873 (4.8); 7.8132 (4.8); 7.7922 (3.7); 7.7870 (3.6); 7.7769 (2.7); 3.9992 (1.8); 3.9529 (2.3); 3.6132 (1.5); 3.5669 (1.2); 3.3300 (10.6); 2.8920 (9.8); 2.7329 (9.5); 2.5616 (16.0); 2.5074 (28.2); 2.5038 (33.5); 1.2378 (0.4); -0.0002 (2.0) I.003: ¹ H-NMR(400.2 MHz, d ₆ -DMSO): δ= 8.6408 (3.3); 8.0426 (1.5); 8.0397 (1.6); 8.0360 (1.7); 8.0328 (1.6); 7.9530 (2.3); 7.8640 (2.7); 7.8430 (4.3); 7.7643 (4.3); 7.7432 (2.9); 7.6922 (1.0); 7.6850 (1.0); 7.6797 (2.0); 7.6725 (1.9); 7.6560 (2.0); 7.6530 (2.1); 7.6434 (1.0); 7.6404 (1.0); 3.9838 (1.5); 3.9376 (1.9); 3.6044 (1.2); 3.5582 (0.9); 3.3300 (20.0); 2.8909 (16.0); 2.7318 (14.2); 2.5247 (0.5); 2.5113 (10.6); 2.5071 (21.5); 2.5026 (28.2); 2.4981 (20.2); 2.4937 (9.7); -0.0002 (2.2) I.004: ¹ H-NMR(300.2 MHz, d ₆ -DMSO): δ= 9.1343 (0.5); 8.3485 (0.5); 7.8486 (0.6); 7.7954 (0.6); 7.4222 (0.4); 3.3477 (16.0); 2.5337 (1.7); 2.5278 (3.5); 2.5218 (4.8); 2.5157 (3.5); 2.5098 (1.6); 0.0198 (5.1) I.005: ¹ H-NMR(300.2 MHz, d ₆ -DMSO): δ= 8.6389 (0.4); 8.3337 (0.4); 7.9884 (0.5); 7.7096 (2.0); 5.7795 (0.6); 4.1899 (0.4); 4.1656 (0.4); 3.3469 (16.0); 2.5343 (1.4); 2.5285 (2.9); 2.5224 (4.0); 2.5163 (2.9); 2.5104 (1.4); 1.4551 (0.4); 1.4309 (1.0); 1.4067 (0.4); 0.0207 (4.7) I.006: ¹ H-NMR(400.2 MHz, d ₆ -DMSO): δ= 8.6497 (4.2); 7.7555 (0.6); 7.7473 (0.4); 7.7321 (16.0); 7.7166 (0.4); 7.70884 (0.6); 7.4827 (3.3); 7.4800 (3.4); 7.2031 (3.3); 3.9709 (1.8); 3.9247 (2.3); 3.5870 (1.4); 3.5404 (1.1); 3.3316 (14.6); 2.8912 (1.2); 2.7322 (1.1); 2.5254 (0.5); 2.5120 (9.2); 2.5077 (18.4); 2.5031 (24.0); 2.4986 (17.1); 2.4941 (8.2); 2.2514 (11.2); 2.2500 (11.2); 1.2370 (0.4); -0.0002 (2.2) I.007: ¹ H-NMR(300.2 MHz, d ₆ -DMSO): δ= 8.6290 (0.6); 8.3062 (1.2); 8.0004 (1.3); 7.7117 (6.0); 3.9857 (0.5); 3.9669 (1.1); 3.9429 (1.1); 3.9243 (0.6); 3.6047 (0.4); 3.3471 (16.0); 2.5279 (3.9); 2.5219 (5.2); 2.5159 (3.8); 0.8981 (4.0); 0.8758 (3.9); 0.0200 (5.2) I.008: ¹ H-NMR(400.1 MHz, d ₆ -DMSO): δ= 8.7200 (0.8); 8.2670 (4.4); 8.1624 (3.6); 8.1434 (4.2); 8.0919 (3.8); 8.0727 (4.0); 7.9613 (3.7); 7.9027 (4.1); 7.8832 (3.6); 7.5225 (1.8); 7.5039 (3.8); 7.4856 (2.4); 7.4224 (1.4); 7.4052 (1.8); 7.3857 (0.7); 4.0384 (1.6); 3.9918 (2.0); 3.6454 (1.8); 3.5989 (1.4); 3.3186 (97.0); 2.9000 (16.0); 2.7410 (15.2); 2.5106 (14.9) I.009: ¹ H-NMR(400.2 MHz, d ₆ -DMSO): δ= 8.6593 (5.1); 7.9527 (0.4); 7.7929 (2.5); 7.7871 (1.2); 7.7710 (16.0); 7.7617 (15.4); 7.7456 (1.3); 7.7396 (2.6); 7.6641 (3.7); 7.6614 (4.5); 7.6550 (4.1); 7.6523 (4.5); 7.6402 (4.6); 7.6376 (4.0); 7.6276 (4.9); 7.6250 (4.0); 7.1933 (4.2); 7.1842 (4.2); 7.1807 (4.1); 7.1715 (3.9); 3.9791 (3.6); 3.9329 (4.5); 3.5947 (2.6); 3.5482 (2.1); 3.3271 (28.5); 2.8912 (2.8); 2.7326 (2.4); 2.7317 (2.3); 2.6715 (0.4); 2.5250 (1.2); 2.5200 (2.0); 2.5116 (27.4); 2.5071 (55.5); 2.5026 (72.3); 2.4980 (50.8); 2.4935 (23.7); 2.3294 (0.4); 1.2393 (0.7); -0.0002 (6.4) I.010: ¹ H-NMR(400.1 MHz, CDCl3): δ= 8.0152 (0.5); 7.6143 (1.6); 7.5932 (3.1); 7.5454 (3.0); 7.5239 (1.7); 7.5175 (0.7); 7.2585 (85.0) ); 6.9914 (1.0); 6.9865 (1.6); 6.9819 (1.0); 6.6555 (0.8); 6.6495 (1.4); 6.6437 (1.0); 6.4760 (1.0); 6.4712 (1.2); 6.4645 (1.0); 4.0869 (0.4 ); 3.7480 (1.0); 3.7202 (0.3); 3.7041 (10.7); 3.5491 (1.0); 3.5070 (0.8); 3.3613 (0.6); 3.1011 (0.4); 3.0701 (0.3); 2.9536 (3.8); 2.8810 (3.4 ); 1.5334 (32.8); 1.4308 (0.4); 1.4043 (0.6); 1.3701 (0.9); 1.3325 (1.2); 1.2842 (3.0); 1.2567 (16.0); 1.1591 (0.7); 1.0785 (0.6); 0.9387 (0.5 ); 0.8954 (1.5); 0.8806 (3.1); 0.8630 (2.2); 0.8537 (2.4); 0.8360 (2.0); 0.1460 (0.5); 0.0079 (5.3); -0.0002 (105.3); -0.0082 (5.3);- 0.1498 (0.5) I.011: ¹ H-NMR(499.9 MHz, d ₆ -DMSO): δ= 8.8512 (15.7); 8.6399 (9.8); 8.3782 (15.4); 7.9755 (3.2); 7.8570 (7.8); 7.8468 (10.4); 7.8301 (16.0); 7.7675 (15.3); 7.7507 (10.7); 7.7386 (3.9); 3.9754 (6.0); 3.9384 (7.3); 3.6032 (5.0); 3.5661 (4.2); 3.3301 (5.0); 2.5082 (4.6); 2.5051 (6.2); 2.5018 (5.1); -0.0002 (2.4) I.012: ¹ H-NMR(300.2 MHz, d ₆ -DMSO): δ= 8.6505 (0.5); 7.7822 (0.8); 7.7541 (0.9); 7.4003 (0.9); 7.3722 (0.8); 3.9420 (0.4); 3.7288 (2.8); 3.3481 (16.0); 2.5340 (1.6); 2.5280 (3.4); 2.5219 (4.7); 2.5159 (3.3); 2.5100 (1.5); 2.2615 (3.3); 2.1679 (3.2); 2.0094 (0.3); 0.0201 (5.4) I.013: ¹ H-NMR(300.2 MHz, d ₆ -DMSO): δ= 8.7270 (0.6); 7.8766 (1.6); 7.8485 (1.9); 7.5812 (2.2); 7.5769 (2.0); 7.5710 (1.5); 7.5532 (1.6); 6.4022 (1.8); 6.3962 (1.8); 4.5829 (0.4); 4.5610 (0.5); 4.5392 (0.4); 4.0376 (0.9); 3.9760 (0.9); 3.6482 (0.6); 3.5851 (0.4); 3.3454 (16.0); 2.5340 (1.9); 2.5280 (4.0); 2.5220 (5.4); 2.5159 (3.9); 2.5100 (1.8); 2.0092 (0.9); 1.4119 (3.8); 1.4085 (3.8); 1.3902 (3.8); 1.3868 (3.7); 1.1946 (0.5); 0.0200 (8.1) I.014: ¹ H-NMR(400.1 MHz, d ₆ -DMSO): δ= 8.6578 (1.7); 7.9520 (2.0); 7.8267 (5.1); 7.8051 (14.7); 7.7820 (14.2); 7.7604 (5.1); 7.7322 (5.9); 7.7291 (7.7); 7.7110 (8.6); 7.6975 (7.0); 7.6878 (8.1); 7.5988 (8.1); 7.5892 (6.9); 7.4718 (4.3); 7.4533 (8.8); 7.4337 (5.4); 7.3648 (3.2); 7.3464 (4.5); 7.3279 (1.7); 3.9821 (4.0); 3.9360 (5.0); 3.6019 (3.3); 3.5557 (2.6); 3.3039 (108.0); 2.8901 (16.0); 2.7481 (0.4); 2.7315 (12.8); 2.5091 (12.4); 2.5048 (23.4); 2.5004 (30.4); 2.4960 (21.8); 1.2329 (0.6); 0.0078 (1.9); -0.0002 (34.8); -0.0083 (1.4) I.015: ¹ H-NMR(400.2 MHz, d ₆ -DMSO): δ= 9.9407 (16.0); 8.7090 (6.2); 8.0872 (6.2); 8.0772 (6.7); 7.9541 (1.9); 7.9446 (6.3); 7.9233 (9.4); 7.8823 (6.3); 7.8724 (5.9); 7.8328 (8.9); 7.8114 (6.4); 7.6927 (0.9); 7.6782 (0.9); 4.0067 (3.2); 3.9728 (0.3); 3.9604 (4.1); 3.6210 (2.4); 3.5741 (2.1); 3.3308 (18.9); 2.8924 (12.2); 2.7338 (10.2); 2.7329 (10.5); 2.5266 (0.9); 2.5219 (1.3); 2.5132 (18.5); 2.5088 (38.5); 2.5042 (50.9); 2.4996 (36.5); 2.4951 (17.5); 1.2374 (0.4); -0.0002 (5.1) I.016: ¹ H-NMR(300.2 MHz, d ₆ -DMSO): δ= 8.6885 (3.7); 8.2877 (4.1); 8.2854 (4.0); 7.8226 (5.2); 7.7944 (6.3); 7.5425 (5.3); 7.5149 (4.4); 4.0840 (0.3); 4.0602 (1.0); 4.0365 (1.0); 4.0122 (2.8); 3.9906 (15.3); 3.9503 (3.1); 3.6281 (1.8); 3.5663 (1.4); 3.3527 (16.0); 2.5340 (2.0); 2.5281 (4.2); 2.5221 (5.6); 2.5160 (4.0); 2.5102 (1.8); 2.0127 (1.2); 2.0085 (4.1); 1.2175 (1.1); 1.1938 (2.2); 1.1701 (1.1); 0.0183 (6.4) I.017: ¹ H-NMR(300.2 MHz, d ₆ -DMSO): δ= 8.7104 (2.1); 8.3085 (1.1); 8.3022 (1.2); 8.0112 (1.4); 7.8963 (0.6); 7.8696 (1.1); 7.8413 (0.6); 7.6434 (0.7); 7.6381 (0.8); 7.6028 (1.8); 7.5808 (0.9); 7.5752 (0.6); 4.2573 (0.6); 4.2331 (1.8); 4.2089 (1.9); 4.1847 (0.6); 4.0062 (0.8); 3.9441 (1.1); 3.6252 (0.6); 3.5637 (0.5); 3.3616 (16.0); 2.5344 (3.3); 2.5284 (6.8); 2.5224 (9.4); 2.5163 (6.8); 2.5104 (3.3); 1.4546 (2.2); 1.4304 (4.9); 1.4061 (2.1); 0.0312 (0.4); 0.0203 (11.0); 0.0094 (0.5) I.018: ¹ H-NMR(400.1 MHz, d ₆ -DMSO): δ= 8.6246 (3.8); 7.7307 (16.0); 7.4930 (1.6); 7.4840 (1.7); 7.0182 (1.3); 7.0095 (1.2); 3.9672 (1.3); 3.9211 (1.7); 3.6913 (3.6); 3.6016 (2.6); 3.5901 (3.8); 3.5809 (3.4); 3.5363 (0.9); 3.3043 (58.7); 2.8902 (1.1); 2.7313 (0.9); 2.5046 (9.6); 2.5002 (12.7); 2.4958 (9.3); 2.4331 (2.7); -0.0002 (5.7) I.019: ¹ H-NMR(400.1 MHz, d ₆ -DMSO): δ= 8.6109 (3.9); 7.9519 (0.6); 7.7854 (2.4); 7.7638 (5.0); 7.7230 (4.8); 7.7014 (2.3); 7.5731 (2.8); 7.5592 (3.0); 7.1814 (3.1); 7.1675 (2.9); 3.9348 (16.0); 3.8958 (1.9); 3.5683 (1.2); 3.5221 (1.0); 3.3037 (55.5); 2.8901 (4.0); 2.7310 (3.3); 2.5088 (4.5); 2.5046 (8.8); 2.5001 (11.6); 2.4957 (8.5); 0.0079 (0.4); -0.0002 (8.2); -0.0083 (0.4) I.020: ¹ H-NMR(400.1 MHz, d ₆ -DMSO): δ= 8.6875 (3.6); 8.056 (4.1); 7.9862 (5.2); 7.8425 (5.1); 7.8225 (4.1); 7.7229 (4.9); 4.0073 (2.0); 3.9609 (2.6); 3.6138 (2.2); 3.5675 (1.7); 3.3184 (114.8); 3.2833 (1.6); 3.2667 (0.7); 2.8994 (0.9); 2.7406 (0.9); 2.6201 (0.4); 2.5105 (15.6); 1.3544 (16.0); 1.3376 (15.6) I.021: ¹ H-NMR(400.2 MHz, d ₆ -DMSO): δ= 8.6294 (3.7); 8.3198 (2.6); 7.9537 (1.4); 7.7849 (1.8); 7.7807 (2.8); 7.7767 (1.7); 7.7581 (0.5); 7.7556 (0.6); 7.7356 (16.0); 7.7129 (0.3); 7.0504 (2.2); 7.0477 (2.2); 3.9724 (1.5); 3.9261 (1.9); 3.5961 (1.2); 3.5490 (0.9); 3.3319 (11.3); 2.8915 (9.1); 2.7325 (8.1); 2.5119 (10.7); 2.5078 (19.0); 2.5034 (23.7); 2.4989 (17.1); -0.0002 (1.8) I.022: ¹ H-NMR(400.1 MHz, CDCl3): δ= 8.0700 (1.9); 7.8475 (1.4); 7.8275 (2.7); 7.8076 (1.6); 7.7827 (5.0); 7.7506 (4.9); 7.4142 (10.5) ); 7.3257 (2.2); 7.3054 (2.0); 7.2602 (2.0); 7.2288 (2.0); 3.9642 (16.0); 3.7518 (1.3); 3.7052 (2.1); 3.5663 (1.8); 3.5218 (1.1); 2.9657 (0.5 ); 2.8766 (0.5); 2.6050 (5.5); 1.2572 (4.8); 0.8786 (0.9); 0.8534 (0.8); -0.0002 (10.8) I.023: ¹ H-NMR(400.1 MHz, CDCl3): δ= 8.7504 (16.0); 8.5964 (16.0); 8.0093 (0.6); 7.7370 (9.3); 7.7160 (11.9); 7.5650 (12.1); 7.5439 (9.3 ); 7.2589 (44.4); 3.8141 (4.6); 3.7694 (6.6); 3.6222 (2.3); 3.5719 (4.6); 3.5272 (3.2); 2.9546 (4.0); 2.8784 (3.6); 1.5979 (0.4); 1.5491 (12.6 ); 1.3701 (0.4); 1.3318 (0.6); 1.2842 (1.5); 1.2567 (8.4); 1.0891 (0.3); 0.8969 (0.8); 0.8807 (1.7); 0.8628 (1.1); 0.8540 (1.1); 0.8363 (1.0 ); 0.8137 (0.6); 0.0078 (2.5); -0.0002 (53.4) I.024: ¹ H-NMR(499.9 MHz, d ₆ -DMSO): δ= 8.6526 (2.3); 8.4647 (3.1); 8.0777 (3.2); 7.7517 (16.0); 7.4304 (0.8); 7.4276 (0.4); 7.4166 (2.3); 7.4016 (2.1); 7.3720 (0.9); 7.3696 (0.8); 7.3576 (1.3); 7.3509 (2.4); 7.3480 (2.5); 7.3434 (1.0); 7.3343 (1.7); 5.4149 (5.0); 4.0048 (1.3); 3.9679 (1.5); 3.6288 (0.9); 3.5917 (0.8); 3.3764 (1.8); 2.5643 (0.8); 2.5610 (1.7); 2.5574 (2.4); 2.5538 (1.8); 2.5504 (0.9) I.025: ¹ H-NMR(300.2 MHz, d ₆ -DMSO): δ= 8.6223 (1.0); 8.2944 (0.8); 8.096 (0.9); 7.7133 (4.1); 4.3194 (0.4); 4.3021 (0.7); 4.2840 (0.4); 3.9273 (0.4); 3.7568 (0.4); 3.7389 (0.7); 3.7215 (0.4); 3.3459 (16.0); 3.2642 (4.0); 2.5336 (1.9); 2.5279 (3.8); 2.5219 (5.2); 2.5159 (3.8); 2.5103 (1.8); 0.0203 (4.6) I.026: ¹ H-NMR(499.9 MHz, d ₆ -DMSO): δ= 8.3227 (4.5); 7.9779 (4.6); 7.7235 (2.0); 7.7065 (6.1); 7.6884 (6.0); 7.6714 (2.2); 4.2916 (1.0); 4.2532 (1.6); 4.1856 (1.2); 4.1710 (3.7); 4.1561 (5.3); 4.1419 (1.3); 4.1161 (1.5); 3.3183 (9.9); 2.5077 (3.2); 2.5043 (4.2); 2.5009 (3.2); 2.1526 (16.0); 1.4330 (4.2); 1.4184 (8.7); 1.4038 (4.1) I.027: ¹ H-NMR(300.2 MHz, d ₆ -DMSO): δ= 8.6243 (0.5); 8.3223 (0.7); 7.9943 (0.7); 7.7102 (3.6); 4.1258 (0.3); 4.1027 (0.7); 4.0796 (0.3); 3.9240 (0.4); 3.3452 (16.0); 2.5336 (1.7); 2.5279 (3.4); 2.5219 (4.6); 2.5159 (3.3); 2.5102 (1.6); 1.8545 (0.4); 1.8308 (0.4); 0.9001 (0.7); 0.8756 (1.4); 0.8509 (0.6); 0.0203 (4.1) I.028: ¹ H-NMR(499.9 MHz, d ₆ -DMSO): δ= 8.6583 (1.0); 8.3355 (5.7); 8.0707 (5.9); 7.7824 (1.0); 7.7808 (0.9); 7.7770 (0.8); 7.7645 (12.6); 7.7616 (13.2); 7.7493 (0.7); 7.7437 (1.1); 5.0477 (10.3); 4.0163 (2.2); 3.9795 (2.7); 3.6389 (1.7); 3.6019 (1.4); 3.3840 (1.3); 2.5680 (1.5); 2.5645 (3.2); 2.5609 (4.4); 2.5573 (3.3); 2.5539 (1.7); 1.9689 (16.0); -0.0002 (0.8) I.029: ¹ H-NMR(400.2 MHz, d ₆ -DMSO): δ= 8.6254 (3.2); 7.9532 (2.5); 7.7336 (15.2); 6.9859 (1.8); 6.9778 (1.8); 6.2556 (1.3); 6.2498 (1.3); 3.9658 (1.2); 3.9196 (1.5); 3.5796 (1.0); 3.5337 (0.8); 3.3286 (13.1); 2.8913 (16.0); 2.7321 (14.5); 2.5111 (9.4); 2.5072 (18.4); 2.5028 (23.9); 2.4983 (17.5); 2.4665 (0.5); 2.3615 (8.2); -0.0002 (1.8) I.030: ¹ H-NMR(400.1 MHz, CDCl3): δ= 7.8624 (3.4); 7.7928 (4.4); 7.6952 (4.5); 7.6545 (3.4); 7.6337 (5.0); 7.5292 (4.8); 7.5083 (3.7 ); 7.3282 (14.5); 7.3180 (3.0); 3.9620 (16.0); 3.9525 (3.7); 3.7448 (1.8); 3.7003 (2.6); 3.5195 (1.9); 3.4750 (1.3); 2.5801 (0.6); 2.5759 (0.5 ); 2.2751 (11.9); 1.2860 (0.9); 1.2566 (4.6); 0.8804 (0.9); 0.8534 (0.8); 0.8366 (0.7); -0.0002 (16.5); -0.0094 (3.6) I.031: ¹ H-NMR(300.2 MHz, d ₆ -DMSO): δ= 8.8900 (0.9); 8.6608 (1.0); 8.4199 (0.9); 7.9296 (0.6); 7.9013 (0.9); 7.7819 (0.9); 7.7537 (0.6); 3.9533 (0.4); 3.3447 (16.0); 2.5342 (1.6); 2.5282 (3.4); 2.5222 (4.7); 2.5161 (3.4); 2.5102 (1.6); 1.6322 (8.7); 0.0203 (5.6) I.032: ¹ H-NMR(300.2 MHz, d ₆ -DMSO): δ= 8.0383 (0.8); 7.7503 (0.6); 7.7221 (0.8); 7.5696 (0.8); 7.5414 (0.6); 3.9221 (0.4); 3.8130 (2.5); 3.3462 (16.0); 2.5338 (2.0); 2.5278 (4.1); 2.5218 (5.6); 2.5158 (4.1); 2.5099 (1.9); 2.3473 (2.7); 0.0201 (5.9) I.033: ¹ H-NMR(300.2 MHz, d ₆ -DMSO): δ= 8.6213 (1.3); 8.3662 (2.9); 7.9880 (3.0); 7.7466 (0.4); 7.7159 (9.8); 7.6843 (0.4); 4.7491 (0.6); 4.7250 (0.9); 4.7033 (0.6); 3.9855 (1.0); 3.9240 (1.4); 3.6060 (0.9); 3.5432 (0.7); 3.3464 (16.0); 2.5337 (2.3); 2.5279 (4.6); 2.5219 (6.2); 2.5159 (4.5); 2.5101 (2.1); 2.1541 (0.4); 2.1360 (0.7); 2.1103 (0.9); 2.0924 (0.7); 2.0710 (0.4); 2.0088 (0.9); 1.9868 (0.9); 1.9680 (0.7); 1.9420 (0.5); 1.8543 (0.6); 1.8411 (0.8); 1.8278 (0.9); 1.8044 (0.7); 1.6990 (0.7); 1.6888 (0.6); 1.6848 (0.8); 1.6780 (0.9); 1.6599 (0.7); 1.6500 (0.5); 0.0198 (5.0) I.034: ¹ H-NMR(300.2 MHz, d ₆ -DMSO): δ= 9.4933 (2.0); 8.8031 (0.4); 8.2948 (1.9); 8.2896 (2.7); 8.2841 (1.6); 7.9963 (0.9); 7.9869 (0.5); 7.9656 (8.0); 7.9569 (8.0); 7.9355 (0.6); 7.9260 (1.0); 7.7882 (2.4); 4.0634 (1.6); 4.0014 (2.1); 3.6990 (1.3); 3.6365 (1.0); 2.9892 (0.3); 2.5340 (2.3); 2.5280 (5.2); 2.5220 (7.3); 2.5159 (5.4); 2.5100 (2.7); 1.9285 (16.0); 1.3886 (0.3); 0.0188 (8.7); 0.0079 (0.4) I.035: ¹ H-NMR(300.2 MHz, CDCl3): δ= 8.2691 (2.0); 8.0854 (1.9); 7.7943 (1.3); 7.7685 (1.6); 7.7574 (1.3); 7.7289 (2.4); 7.6826 (2.4) ); 7.6540 (1.1); 7.5604 (0.8); 7.5356 (1.4); 7.5080 (0.9); 7.4012 (0.5); 7.3766 (0.8); 7.3518 (0.3); 7.2984 (26.3); 3.8226 (0.7); 3.7634 (1.2 ); 3.6204 (0.8); 3.5628 (0.5); 3.4509 (1.4); 1.5843 (16.0); 0.1074 (0.3); 0.0486 (1.6); 0.0379 (33.9); 0.0271 (1.5) I.036: ¹ H-NMR(400.1 MHz, d ₆ -DMSO): δ= 8.5830 (1.1); 8.3682 (3.1); 8.0174 (3.2); 7.7124 (0.5); 7.7070 (0.4); 7.6887 (16.0); 7.6751 (1.6); 7.6530 (0.4); 7.4904 (1.3); 7.4874 (1.4); 7.4777 (1.4); 7.4747 (1.4); 7.1493 (1.2); 7.1429 (1.3); 7.0195 (1.3); 7.0108 (1.3); 7.0069 (1.3); 6.9982 (1.1); 5.5461 (5.2); 3.9667 (0.4); 3.9475 (1.2); 3.9201 (0.4); 3.9014 (1.5); 3.5703 (1.2); 3.5241 (1.0); 3.3038 (50.0); 2.9466 (0.4); 2.8899 (1.3); 2.7309 (1.1); 2.5085 (5.0); 2.5044 (9.6); 2.4999 (12.7); 2.4955 (9.3); 0.0078 (0.4); -0.0002 (7.8) I.037: ¹ H-NMR(300.2 MHz, d ₆ -DMSO): δ= 8.7470 (3.3); 7.9774 (4.2); 7.9492 (8.5); 7.8977 (8.4); 7.8696 (4.0); 7.0401 (8.0); 4.0434 (2.6); 3.9814 (3.4); 3.6498 (2.4); 3.5877 (1.8); 3.3532 (16.0); 2.5270 (7.1); 2.5216 (8.7); 2.5161 (6.5); 2.3234 (20.6); 0.0179 (7.7) I.038: ¹ H-NMR(499.9 MHz, d ₆ -DMSO): δ= 8.7109 (10.4); 8.6588 (2.9); 7.9713 (6.5); 7.9545 (8.4); 7.8188 (8.1); 7.8020 (6.8); 4.4712 (2.2); 4.4566 (6.8); 4.4419 (6.9); 4.4272 (2.2); 3.9849 (3.3); 3.9480 (4.0); 3.6105 (2.5); 3.5734 (2.1); 3.3559 (1.5); 2.5079 (0.8); 2.5043 (1.1); 2.5008 (0.8); 1.5135 (7.6); 1.4988 (16.0); 1.4842 (7.7) I.039: ¹ H-NMR(400.1 MHz, d ₆ -DMSO): δ= 9.6242 (14.8); 9.2888 (13.7); 9.2856 (11.9); 9.2799 (6.8); 8.7734 (0.5); 8.6936 (11.5); 8.3035 (0.7); 7.9519 (2.4); 7.9038 (0.4); 7.8632 (5.7); 7.8431 (12.4); 7.8237 (13.6); 7.7945 (7.4); 7.6959 (9.4); 7.6754 (7.3); 6.4881 (0.7); 4.0118 (0.4); 3.9957 (0.4); 3.9647 (4.1); 3.9174 (5.2); 3.6041 (7.0); 3.5575 (5.5); 3.5108 (0.4); 3.3918 (0.4); 3.3009 (227.5); 2.8921 (16.0); 2.7335 (13.8); 2.7119 (0.4); 2.6960 (0.4); 2.6743 (0.4); 2.6704 (0.6); 2.5677 (0.7); 2.5099 (29.8); 2.5056 (57.0); 2.5011 (75.0); 2.4966 (53.7); 2.3278 (0.4); 1.3359 (0.4); 1.2981 (0.7); 1.2604 (1.3); 1.2406 (4.5); 1.1770 (0.4); 0.8698 (0.5); 0.8540 (1.1); 0.8379 (0.6); 0.8075 (0.4); -0.0002 (40.8) I.040: ¹ H-NMR(300.2 MHz, CDCl3): δ= 7.8480 (3.2); 7.8462 (3.3); 7.7433 (3.4); 7.6934 (2.5); 7.6649 (4.0); 7.5731 (4.0); 7.5445 (2.5) ); 7.2987 (1.1); 4.2897 (1.0); 4.2653 (3.2); 4.2407 (3.9); 4.2166 (1.1); 4.1826 (3.9); 4.1559 (3.9); 4.0986 (0.8); 4.0468 (0.7); 4.0430 (0.7 ); 3.9858 (1.2); 3.9820 (1.3); 3.8410 (2.2); 3.7801 (1.2); 3.4810 (16.0); 1.5961 (3.5); 1.5717 (7.3); 1.5473 (3.4); 1.2889 (0.4); 0.1199 (1.2) ); 0.1080 (24.6); 0.0972 (1.1); 0.0958 (1.2); 0.0327 (1.1) I.041: ¹ H-NMR(499.9 MHz, d ₆ -DMSO): δ= 8.3229 (4.5); 7.9781 (4.6); 7.7238 (2.0); 7.7068 (6.1); 7.6887 (6.0); 7.6716 (2.2); 4.2916 (0.9); 4.2533 (1.6); 4.1859 (1.2); 4.1714 (3.7); 4.1564 (5.1); 4.1422 (1.4); 4.1164 (1.5); 3.3182 (9.2); 2.5081 (3.0); 2.5046 (4.2); 2.5012 (3.2); 2.1529 (16.0); 1.4333 (4.1); 1.4187 (8.7); 1.4042 (4.2) I.042: ¹ H-NMR(300.2 MHz, d ₆ -DMSO): δ= 8.6843 (0.7); 8.4088 (0.8); 8.0554 (0.8); 7.7619 (0.4); 7.5751 (0.4); 4.1896 (0.7); 4.1653 (0.7); 3.3475 (16.0); 2.5345 (1.6); 2.5286 (3.2); 2.5226 (4.4); 2.5165 (3.3); 2.5107 (1.6); 1.4551 (0.8); 1.4309 (1.7); 1.4066 (0.8); 0.0208 (4.9) I.043: ¹ H-NMR(400.2 MHz, d ₆ -DMSO): δ= 8.6801 (8.8); 7.9535 (2.6); 7.8325 (6.1); 7.8115 (9.2); 7.7303 (9.3); 7.7093 (6.2); 7.6111 (6.0); 7.5967 (6.5); 7.3186 (6.4); 7.3041 (5.9); 3.9989 (3.4); 3.9526 (4.2); 3.6172 (2.6); 3.5707 (2.1); 3.3291 (23.3); 2.8914 (16.0); 2.7324 (14.8); 2.5074 (37.4); 2.5031 (46.2); 2.4987 (33.2); 1.2395 (0.4); -0.0002 (3.2) I.044: ¹ H-NMR(400.2 MHz, d ₆ -DMSO): δ= 8.7075 (11.8); 8.0430 (9.2); 8.0331 (9.8); 7.9028 (7.6); 7.8815 (14.1); 7.8318 (16.0); 7.8241 (10.0); 7.8102 (7.7); 4.0043 (4.6); 3.9579 (5.8); 3.6186 (3.4); 3.5720 (2.8); 3.3297 (25.3); 2.8922 (1.7); 2.7336 (1.4); 2.7327 (1.4); 2.6726 (0.4); 2.5263 (1.3); 2.5215 (2.0); 2.5129 (27.3); 2.5084 (55.6); 2.5039 (72.8); 2.4993 (51.9); 2.4948 (24.9); 2.3307 (0.4); 1.2375 (0.9); -0.0002 (6.8) I.045: ¹ H-NMR(400.1 MHz, CDCl3): δ= 8.0010 (0.8); 7.6969 (3.4); 7.6760 (4.0); 7.4862 (4.1); 7.4652 (3.2); 7.2579 (11.2); 6.7614 (1.5 ); 6.7562 (2.1); 6.7507 (1.4); 6.3244 (1.4); 6.3199 (1.5); 6.3153 (1.8); 6.3110 (1.6); 6.2289 (1.6); 6.2219 (2.0); 6.2132 (1.3); 3.7583 (1.7 ); 3.7137 (3.5); 3.70553 (16.0); 3.5664 (1.6); 3.5220 (1.0); 2.9523 (5.1); 2.8739 (4.8); 1.5624 (1.7); 1.2852 (0.5); 1.2574 (2.7); 0.8808 (0.5 ); 0.8634 (0.4); 0.8539 (0.4); 0.8370 (0.4); -0.0002 (13.9) I.046: ¹ H-NMR(300.2 MHz, CDCl3): δ= 8.2068 (3.2); 8.2006 (1.1); 8.1842 (1.2); 8.1781 (3.6); 7.8214 (3.7); 7.8152 (1.2); 7.7987 (1.1) ); 7.7927 (3.1); 7.2988 (12.4); 3.8264 (1.2); 3.7671 (2.1); 3.6689 (2.6); 3.6245 (1.3); 3.5620 (0.7); 3.4838 (0.8); 3.4570 (1.3); 3.4306 (0.9 ); 2.2606 (0.5); 2.2447 (0.8); 2.2397 (0.6); 2.2173 (1.0); 2.2061 (0.7); 2.2012 (0.6); 2.1783 (0.4); 2.0884 (0.8); 2.0704 (0.7); 2.0631 (1.0) ); 2.0446 (0.7); 2.0374 (0.6); 2.0221 (0.6); 1.9991 (0.3); 1.9506 (0.4); 1.9425 (0.6); 1.9320 (0.7); 1.9142 (0.9); 1.8933 (0.7); 1.8836 (0.4 ); 1.8624 (0.4); 1.8410 (0.5); 1.8086 (0.9); 1.7962 (0.7); 1.7862 (0.9); 1.7695 (0.6); 1.7593 (0.4); 1.6116 (16.0); 0.0482 (0.7); 0.0375 (18.0 ); 0.0267 (0.6) I.047: ¹ H-NMR(300.2 MHz, d ₆ -DMSO): δ= 8.9745 (0.3); 8.9048 (0.4); 8.3833 (1.1); 8.3612 (1.5); 8.3546 (2.0); 8.3337 (2.0); 8.3047 (1.2); 8.2525 (0.3); 8.2147 (5.5); 8.1865 (7.0); 7.9792 (6.8); 7.9512 (5.4); 7.7314 (1.2); 7.7236 (1.3); 7.6933 (2.1); 7.6638 (1.2); 7.6552 (1.3); 7.4738 (1.1); 7.4686 (1.1); 7.4469 (2.0); 7.4175 (1.1); 7.4119 (1.0); 4.0437 (1.9); 3.9814 (2.4); 3.6550 (2.3); 3.6218 (0.5); 3.5930 (1.8); 3.3438 (16.0); 3.2129 (0.5); 3.1832 (0.5); 3.1545 (0.5); 2.7491 (0.4); 2.5890 (0.4); 2.5285 (34.7); 2.5226 (45.4); 2.5166 (33.5); 2.4565 (0.5); 2.2931 (0.3); 1.7806 (0.4); 1.5796 (0.4); 1.3758 (1.0); 1.3432 (0.5); 1.3178 (0.6); 1.2941 (0.4); 0.9811 (1.2); 0.9570 (2.2); 0.9316 (0.8); 0.0206 (43.4) I.048: ¹ H-NMR(300.2 MHz, d ₆ -DMSO): δ= 8.7905 (1.2); 8.2496 (0.8); 8.2209 (1.0); 8.0182 (1.0); 7.9896 (0.8); 4.0909 (0.4); 4.0626 (0.5); 4.0389 (0.6); 4.0290 (0.4); 3.3405 (16.0); 2.5351 (2.1); 2.5291 (4.6); 2.5230 (6.3); 2.5169 (4.5); 2.5110 (2.1); 2.0103 (2.4); 1.2199 (0.6); 1.1962 (1.3); 1.1725 (0.6); 0.0214 (4.1) I.049: ¹ H-NMR(300.2 MHz, d ₆ -DMSO): δ= 8.7824 (2.2); 8.1934 (1.8); 8.1876 (0.7); 8.1708 (0.8); 8.1648 (2.3); 7.9916 (2.3); 7.9854 (0.7); 7.9687 (0.7); 7.9629 (1.7); 7.7636 (0.7); 7.5920 (1.7); 7.4205 (0.8); 4.0780 (0.8); 4.0160 (1.0); 3.6659 (0.6); 3.6036 (0.5); 3.3478 (16.0); 2.5349 (1.2); 2.5289 (2.4); 2.5229 (3.3); 2.5168 (2.4); 2.5109 (1.1); 0.0200 (3.0) I.050: ¹ H-NMR(499.9 MHz, d ₆ -DMSO): δ= 9.8743 (0.4); 9.5335 (0.7); 9.4527 (0.8); 9.4450 (0.8); 9.3743 (0.8); 9.3329 (0.8); 9.2243 (0.7); 9.1586 (0.6); 9.1180 (0.6); 9.1009 (0.6); 9.0290 (0.5); 8.9990 (0.5); 8.9855 (0.5); 8.9401 (0.5); 8.8896 (0.5); 8.8570 (0.5); 8.8250 (0.5); 8.7856 (0.5); 8.7352 (0.4); 8.2632 (0.3); 8.0843 (12.8); 8.0676 (16.0); 7.9933 (0.3); 7.9770 (0.4); 7.9684 (0.4); 7.9519 (0.8); 7.9358 (15.6); 7.9191 (12.8); 7.8480 (0.4); 4.0257 (6.7); 3.9886 (8.1); 3.9323 (0.4); 3.9171 (0.5); 3.9023 (0.4); 3.8968 (0.6); 3.8824 (1.8); 3.8676 (2.6); 3.8530 (1.9); 3.8387 (0.5); 3.6443 (5.6); 3.6070 (4.6); 3.4829 (1.1); 3.4671 (3.7); 3.4514 (5.6); 3.4358 (3.8); 3.4201 (1.2); 3.2896 (0.4); 2.6374 (0.3); 2.5029 (58.7); 2.1344 (1.4); 2.1203 (3.1); 2.1107 (4.4); 2.0949 (5.3); 2.0847 (3.6); 2.0709 (2.1); 2.0148 (0.3); 2.0035 (0.4); 1.9547 (1.6); 1.9416 (4.1); 1.9277 (5.6); 1.9161 (4.5); 1.9028 (3.6); 1.8880 (1.7); 1.7952 (1.1); 1.7890 (1.4); 1.7738 (3.6); 1.7697 (4.0); 1.7583 (5.8); 1.7449 (4.7); 1.7271 (2.5); 1.7182 (3.2); 1.6995 (5.3); 1.6915 (4.6); 1.686 1 (5.8); 1.6768 (4.3); 1.6725 (3.5); 1.6626 (2.1); 1.6521 (1.1); 1.6461 (1.0); 1.6301 (0.5); 1.2324 (1.4); 1.2266 (1.4); 1.2087 (3.2); 1.1944 (5.6); 1.1803 (2.7); -0.0002 (18.0) I.051: ¹ H-NMR(300.2 MHz, CDCl3): δ= 8.1980 (0.6); 8.1692 (0.8); 7.8367 (0.8); 7.8079 (0.6); 7.2988 (8.6); 3.7677 (0.4); 3.6387 (0.6 ); 2.7191 (3.5); 1.5978 (16.0); 0.0480 (0.4); 0.0371 (11.1); 0.0261 (0.4) I.052: ¹ H-NMR(300.2 MHz, CDCl3): δ=8.2206 (9.7); 8.2146 (3.3); 8.1980 (3.7); 8.1918 (11.3); 8.1747 (3.6); 8.1690 (3.4); 8.1495 (4.4) ); 8.1433 (4.0); 7.8665 (11.6); 7.8603 (3.7); 7.8437 (3.4); 7.8377 (9.4); 7.6555 (2.4); 7.6503 (3.1); 7.6283 (4.4); 7.6244 (5.2); 7.5883 (2.2) ); 7.5822 (2.4); 7.5639 (4.4); 7.5577 (4.0); 7.5380 (2.9); 7.5312 (2.7); 7.5264 (3.8); 7.5207 (3.6); 7.5011 (4.1); 7.4960 (4.2); 7.4764 (1.6 ); 7.4715 (1.4); 7.2988 (54.1); 5.3380 (7.4); 4.1945 (1.1); 4.1706 (3.5); 4.1469 (3.5); 4.1231 (1.2); 3.8434 (3.5); 3.7839 (7.1); 3.6797 (4.2 ); 3.6762 (4.3); 3.6203 (2.1); 3.6165 (2.1); 3.1613 (0.6); 3.1392 (0.6); 2.0838 (16.0); 1.8666 (0.4); 1.6555 (2.0); 1.4540 (2.0); 1.4296 (3.5 ); 1.4051 (1.8); 1.3627 (0.5); 1.3400 (0.5); 1.3201 (4.6); 1.2963 (9.5); 1.2725 (4.5); 1.2296 (0.4); 0.8977 (0.6); 0.8770 (0.7); 0.1064 (0.4 ); 0.0474 (1.2); 0.0366 (46.0); 0.0257 (1.8) I.053: ¹ H-NMR(300.2 MHz, d ₆ -DMSO): δ=8.7802 (0.7); 8.1068 (1.3); 8.0781 (2.0); 7.9674 (1.9); 7.9386 (1.3); 4.0676 (0.6); 4.0056 (0.8); 3.6564 (0.5); 3.5940 (0.4); 3.3496 (16.0); 2.6244 (6.8); 2.5345 (1.6); 2.5286 (3.3); 2.5225 (4.5); 2.5165 (3.3); 2.5106 (1.6); 0.0202 (2.6) I.054: ¹ H-NMR(500.1 MHz, CDCl3): δ=8.2130 (3.9); 8.1959 (4.4); 7.9735 (0.7); 7.8674 (4.4); 7.8503 (4.1); 7.2597 (26.8); 7.0713 (0.4) ); 7.0374 (1.2); 6.9340 (2.8); 6.8307 (1.4); 3.7813 (1.9); 3.7457 (2.8); 3.5891 (1.8); 3.5873 (1.9); 3.5536 (1.2); 3.5517 (1.3); 2.6542 (1.1) ); 2.3678 (0.9); 2.3528 (1.5); 2.3377 (1.0); 2.0445 (0.6); 1.6532 (0.5); 1.6388 (0.7); 1.6238 (0.6); 1.6087 (0.4); 1.5552 (2.7); 1.3307 (0.5 ); 1.2989 (1.0); 1.2836 (1.3); 1.2727 (1.9); 1.2553 (16.0); 0.8937 (1.0); 0.8802 (2.6); 0.8660 (1.3); 0.8583 (0.5); 0.8450 (0.6); 0.0062 (0.9 ); -0.0002 (27.4); -0.0066 (1.3) I.055: ¹ H-NMR(300.2 MHz, CDCl3): δ=8.0182 (1.1); 8.0118 (0.7); 7.9895 (1.3); 7.9835 (0.6); 7.9526 (0.9); 7.9451 (0.4); 7.7726 (1.4) ); 7.7660 (0.8); 7.7439 (1.0); 7.7378 (0.5); 7.2988 (8.2); 7.2924 (2.6); 3.7092 (0.4); 3.6496 (0.8); 3.5281 (0.5); 2.1042 (4.1); 2.0965 (2.4) ); 1.5411 (16.0); 1.5348 (5.6); 0.0082 (0.7); -0.0024 (12.0); -0.0086 (3.7) I.056: ¹ H-NMR(300.2 MHz, CDCl3): δ=7.8436 (1.3); 7.8331 (1.5); 7.6943 (1.5); 7.6632 (0.9); 7.6350 (1.5); 7.5600 (1.5); 7.5314 (0.9) ); 7.2988 (8.1); 7.2941 (2.0); 3.7039 (0.4); 3.6448 (0.8); 3.5178 (0.5); 2.0526 (13.1); 2.0479 (3.7); 1.6482 (16.0); 1.6438 (4.7); 1.2574 (0.5 ); 0.0150 (0.4); 0.0044 (9.1); -0.0002 (2.4) I.057: ¹ H-NMR(400.2 MHz, d ₆ -DMSO): δ=8.7214 (1.0); 7.9538 (2.7); 7.9388 (0.8); 7.9041 (0.8); 7.8679 (0.6); 7.8403 (1.0); 7.8145 (1.4); 7.7820 (6.4); 7.7620 (7.5); 7.7286 (0.4); 7.7073 (0.4); 7.6886 (0.4); 7.6706 (0.4); 7.5777 (6.6); 7.5577 (5.6); 7.2820 (0.4); 7.2481 (0.4); 7.2263 (0.4); 5.9989 (0.4); 5.9857 (0.7); 5.9773 (1.1); 5.9644 (1.1); 5.9511 (1.4); 5.9352 (1.4); 5.9213 (1.1); 5.9090 (1.2); 5.2167 (0.5); 5.2108 (0.4); 5.2074 (0.4); 5.1916 (0.5); 5.1418 (3.2); 5.1160 (3.0); 5.099 (0.3); 4.9834 (0.6); 4.9237 (0.6); 4.8661 (2.8); 4.8233 (2.7); 4.7688 (5.1); 4.7615 (5.0); 4.6230 (0.9); 4.6105 (0.9); 4.5819 (0.7); 4.5692 (0.6); 3.9811 (3.2); 3.9349 (4.0); 3.6026 (2.8); 3.5566 (2.2); 3.3392 (13.6); 3.2022 (0.6); 3.1865 (0.6); 2.8910 (14.4); 2.7486 (0.6); 2.7316 (13.7); 2.6722 (0.5); 2.6679 (0.4); 2.5930 (2.0); 2.5825 (0.6); 2.5074 (67.6); 2.5031 (85.5); 2.4988 (64.2); 2.4701 (2.0); 2.3300 (0.5); 1.3109 (6.7); 1.2953 (1.2); 1.2357 (0.4); 1.2205 (0.4); 1.1862 (0.4); 1.1707 (2.6); 1.1589 (16.0); 1.1339 (2.4); 1.0698 (0.6); 0.0080 (0.5); -0.0002 (13.0); -0 .0084 (0.6) I.058: ¹ H-NMR(300.2 MHz, CDCl3): δ=8.2615 (4.3); 8.2325 (4.7); 7.9260 (5.1); 7.8970 (4.0); 7.2983 (30.0); 3.8372 (1.6); 3.8058 (2.0) ); 3.7776 (2.9); 3.6400 (1.9); 3.5906 (2.8); 3.4802 (0.7); 3.4560 (0.7); 1.5989 (16.0); 1.3695 (0.4); 1.3467 (0.5); 1.2919 (2.5); 1.2588 (1.7 ); 1.2349 (0.8); 0.9170 (0.3); 0.8967 (0.4); 0.8760 (0.4); 0.0477 (1.3); 0.0369 (36.3); 0.0278 (1.2); 0.0261 (1.3) I.059: ¹ H-NMR(400.1 MHz, d ₆ -DMSO): δ=14.2935 (0.3); 11.4664 (0.3); 8.8353 (0.3); 8.7575 (11.1); 8.7003 (0.4); 8.2436 (0.4); 8.2147 (0.8); 8.1830 (13.0); 8.1622 (15.4); 8.1037 (0.5); 8.0540 (0.4); 7.9811 (16.0); 7.9603 (13.4); 7.9122 (1.0); 7.8968 (0.6); 7.8077 (0.3); 4.0542 (6.2); 4.0387 (1.2); 4.0071 (7.8); 3.9813 (0.5); 3.6431 (6.0); 3.5952 (5.1); 3.4238 (11.0); 3.3028 (0.6); 3.2725 (0.5); 3.2566 (0.5); 3.2036 (0.4); 3.1637 (0.4); 3.1030 (0.4); 3.0831 (0.4); 3.0181 (0.4); 3.0055 (0.3); 2.9838 (0.4); 2.6704 (0.6); 2.6083 (0.4); 2.5007 (109.5); 2.4564 (2.8); 2.3815 (0.8); 2.3317 (1.1); 2.2896 (0.4); 2.2731 (0.4); 1.9880 (1.8); 1.9080 (0.4); 1.2350 (0.9); 1.2122 (0.4); 1.1921 (0.7); 1.1742 (0.9); 1.1570 (0.6); 0.0333 (1.1); -0.0002 (52.6); -0.0483 (0.9); -0.1231 (0.3); -0.1490 (0.4) I.060: ¹ H-NMR(500.1 MHz, CDCl3): δ=8.6299 (2.7); 8.6248 (2.7); 8.4410 (1.4); 8.4329 (1.4); 8.1183 (1.8); 8.1018 (2.1); 8.0174 (3.5 ); 8.009 (4.0); 7.8693 (0.8); 7.8524 (1.5); 7.8383 (0.7); 7.7490 (3.9); 7.7325 (3.5); 7.4660 (0.4); 7.2595 (67.5); 7.2505 (1.7); 7.2275 (1.2 ); 7.2176 (1.3); 7.2129 (1.2); 7.2031 (1.1); 7.0480 (0.4); 6.8371 (2.6); 6.8320 (2.7); 3.7852 (1.7); 3.7498 (2.5); 3.5909 (1.7); 3.5556 (1.2 ); 3.4918 (0.3); 2.5511 (0.6); 1.5451 (16.0); 1.4227 (0.4); 1.4090 (0.4); 1.3581 (0.4); 1.3330 (0.4); 1.2547 (5.9); 1.2147 (0.6); 0.8937 (0.5 ); 0.8806 (0.8); 0.8663 (0.6); 0.8575 (1.0); 0.8454 (1.2); -0.0002 (60.0); -0.1199 (0.4) I.061: ¹ H-NMR(400.2 MHz, d ₆ -DMSO): δ=9.8382 (13.4); 9.8354 (13.6); 8.7338 (2.7); 8.2159 (6.2); 8.2132 (6.4); 8.2034 (6.5); 8.2006 (6.5); 7.9527 (0.4); 7.8663 (10.0); 7.8453 (16.0); 7.7659 (15.7); 7.7450 (10.5); 7.4926 (11.5); 7.4801 (11.3); 4.0245 (5.4); 3.9781 (6.8); 3.6371 (4.1); 3.5907 (3.3); 3.3329 (26.3); 2.8912 (2.3); 2.7315 (2.0); 2.6765 (0.3); 2.6720 (0.4); 2.6677 (0.3); 2.5252 (1.5); 2.5120 (28.3); 2.5076 (55.4); 2.5031 (71.7); 2.4986 (51.6); 2.4941 (25.1); 2.3299 (0.4); 1.2391 (0.5); -0.0002 (5.2) I.062: ¹ H-NMR(400.2 MHz, d ₆ -DMSO): δ=9.9981 (3.3); 9.951 (3.3); 8.6814 (1.8); 8.6166 (1.6); 8.6134 (2.8); 8.6101 (1.9); 8.5853 (3.0); 8.5816 (2.4); 7.9543 (2.3); 7.9312 (2.7); 7.9100 (3.9); 7.8235 (4.0); 7.8024 (2.7); 4.0046 (1.4); 3.9583 (1.8); 3.6242 (1.1); 3.5778 (0.9); 3.3385 (19.0); 2.8919 (16.0); 2.7328 (13.7); 2.5130 (7.4); 2.5087 (14.1); 2.5042 (17.8); 2.4997 (12.7); 2.4953 (6.2); -0.0002 (1.0) I.063: ¹ H-NMR(400.2 MHz, d ₆ -DMSO): δ=9.7267 (10.2); 8.7179 (2.4); 7.9535 (1.9); 7.8521 (4.8); 7.8313 (6.8); 7.7260 (6.6); 7.7052 (4.7); 7.2253 (4.6); 7.2237 (4.4); 4.0199 (2.4); 3.9734 (3.0); 3.6300 (1.9); 3.5836 (1.5); 3.3375 (29.2); 2.8917 (13.5); 2.7323 (11.7); 2.5827 (16.0); 2.5257 (0.5); 2.5122 (11.5); 2.5080 (22.4); 2.5036 (28.7); 2.4991 (20.7); 2.4948 (10.3); -0.0002 (1.5) I.064: ¹ H-NMR(600.2 MHz, d ₆ -DMSO): δ=8.8746 (2.4); 8.2900 (0.5); 8.2772 (0.6); 8.2294 (1.0); 8.1904 (14.5); 8.1774 (15.8); 7.9658 (16.0); 7.9528 (14.6); 4.0270 (6.1); 3.9961 (7.1); 3.6345 (6.9); 3.6035 (6.0); 3.3267 (2.4); 3.1684 (0.8); 2.5526 (0.5); 2.5078 (21.4); 2.4466 (44.3); 2.3365 (0.4); 1.5737 (0.8); 1.3226 (0.8); 1.3109 (0.9); 0.9543 (1.2); 0.9427 (2.0); 0.9313 (1.1) I.065: ¹ H-NMR(300.2 MHz, CDCl3): δ=7.9344 (1.0); 7.9054 (1.2); 7.6948 (1.3); 7.6673 (1.0); 7.6657 (1.0); 7.2987 (10.1); 5.7105 (0.8 ); 3.8346 (0.3); 3.7747 (0.9); 3.7073 (0.6); 1.5949 (7.6); 1.5526 (16.0); 1.2910 (0.4); 0.0480 (0.5); 0.0464 (0.4); 0.0372 (14.1); 0.0281 (0.5 ); 0.0264 (0.5) I.066: ¹ H-NMR(400.2 MHz, d ₆ -DMSO): δ= 9.1551 (4.5); 8.6972 (3.5); 8.6480 (0.5); 8.4609 (5.2); 7.9556 (3.3); 7.8377 (2.2); 7.8167 (7.8); 7.8028 (7.6); 7.7818 (2.2); 7.7369 (0.6); 7.7204 (0.6); 7.5052 (1.0); 7.4871 (0.6); 4.0002 (2.2); 3.9686 (0.6); 3.9538 (2.8); 3.9224 (0.5); 3.6142 (2.0); 3.5677 (1.7); 3.3428 (18.7); 2.8924 (16.0); 2.7507 (0.4); 2.7333 (15.8); 2.5054 (35.2); 1.2445 (0.8); 1.2083 (1.1); 1.1859 (1.4); 1.1705 (1.3); 1.1648 (1.5); 1.1534 (1.9); 1.1315 (1.2); 1.1200 (1.3); 1.0970 (0.5); 1.0716 (0.4); -0.0002 (2.4) I.067: ¹ H-NMR(400.2 MHz, d ₆ -DMSO): δ= 8.7258 (8.7); 8.6499 (9.3); 8.6462 (9.4); 7.9555 (0.6); 7.9249 (9.1); 7.9214 (9.1); 7.8973 (6.0); 7.8763 (16.0); 7.8535 (15.6); 7.8324 (5.9); 4.0188 (4.9); 3.9724 (6.2); 3.6296 (4.3); 3.5830 (3.5); 3.3496 (54.1); 2.8930 (3.1); 2.7340 (2.9); 2.5103 (36.3); 2.5063 (45.0); 2.5022 (34.6); 1.1706 (0.3); -0.0002 (3.3) I.068: ¹ H-NMR(400.2 MHz, d ₆ -DMSO): δ=9.5040 (14.6); 9.4914 (1.2); 9.1502 (16.0); 9.1370 (1.2); 8.6853 (9.3); 7.9582 (9.9); 7.9375 (13.1); 7.8178 (13.0); 7.7970 (10.2); 4.0053 (5.3); 3.9589 (6.6); 3.6258 (4.6); 3.5793 (3.6); 3.3597 (111.7); 2.8926 (2.1); 2.7338 (2.0); 2.5107 (35.8); 2.5065 (45.8); 2.5024 (36.6) I.069: ¹ H-NMR(300.2 MHz, CDCl3): δ=7.9823 (2.6); 7.9535 (2.8); 7.7515 (3.2); 7.7241 (2.2); 7.2986 (38.2); 4.8934 (1.1); 3.8171 (0.9 ); 3.7579 (1.9); 3.6484 (1.2); 3.5912 (0.6); 2.3064 (0.4); 2.2906 (0.4); 2.2810 (1.0); 2.2599 (0.5); 1.5943 (16.0); 1.3051 (6.0); 1.2900 (3.1 ); 1.2780 (2.4); 0.8974 (0.4); 0.8777 (0.4); 0.0477 (1.9); 0.0369 (54.6); 0.0260 (2.0) I.070: ¹ H-NMR(300.2 MHz, CDCl3): δ=7.8502 (0.8); 7.8461 (0.8); 7.6883 (0.5); 7.6601 (0.8); 7.5804 (0.8); 7.5520 (0.4); 7.2986 (19.6) ); 4.0868 (0.8); 4.0632 (0.8); 3.7593 (0.4); 3.7446 (0.4); 1.5873 (16.0); 1.2894 (0.5); 0.7535 (0.3); 0.7302 (0.3); 0.4766 (0.4); 0.4572 (0.4) ); 0.0478 (1.0); 0.0371 (27.8); 0.0263 (1.2) I.071: ¹ H-NMR(300.2 MHz, CDCl3): δ=7.8683 (2.5); 7.7674 (14.8); 7.7566 (5.3); 7.6416 (5.6); 7.6159 (8.6); 7.6057 (3.4); 7.5149 (8.2) ); 7.5069 (4.2); 7.4892 (6.0); 7.3011 (20.7); 7.2974 (17.8); 7.2888 (7.1); 3.6759 (2.8); 3.6608 (1.6); 3.6461 (1.9); 3.6356 (2.8); 3.6180 (6.1 ); 3.4929 (3.9); 3.4334 (2.1); 2.5648 (0.9); 2.2054 (16.0); 1.9995 (0.3); 1.2379 (2.4); 1.1934 (1.0); 1.1804 (1.9); 1.1631 (5.1); 1.1538 (5.8 ); 1.1509 (5.8); 1.1376 (3.5); 1.1150 (1.0); 1.1028 (1.1); 1.0870 (2.4); 1.0706 (4.2); 1.0664 (4.5); 1.0461 (4.8); 1.0236 (1.5); 0.8257 (0.5 ); -0.0138 (30.4); -0.0174 (27.9); -0.0260 (11.6); -0.0803 (0.4) Biological Data Example: In vivo Puccinia recondita (Puccinia recondita) (wheat brown rust) Prevention of test Solvent: 5% by volume of acetone Emulsifier ratio of dimethyl sulfoxide to 10% by volume: [mu] l of Tween ^® 80 / per Milligram (mg) active ingredient

The active ingredient is dissolved in a ^{mixture of dimethyl sulfoxide/acetone/Tween ®} 80 and homogenized, and then diluted with water to the desired concentration.

The young wheat plants are treated by spraying the active ingredients prepared as described above. The control plants were only treated with an aqueous solution of acetone/dimethyl sulfoxide/Tween ^{® 80.}

After 24 hours, the leaves were sprayed with an aqueous suspension of Puccinia cryptica spores to infect the plants. The infected wheat plants were incubated at 20°C and 100% relative humidity for 24 hours and then at 20°C and 70-80% relative humidity for 9 days.

The test is evaluated 10 days after vaccination. 0% means that the utility is equivalent to the control plant, and 100% means that no disease is observed.

In this test, the following compounds according to the present invention showed an efficacy ranging from 70% to 79% at an active ingredient concentration of 250 ppm: I.012; I.013; I.037

In this test, the following compounds according to the present invention showed an efficacy ranging from 80% to 89% at an active ingredient concentration of 250 ppm: I.008; I.011; I.020; I.022; I.032 ; I.038; I.046; I.048; I.052

In this test, the following compounds according to the present invention exhibited effects ranging from 90% to 100% at an active ingredient concentration of 250 ppm: I.015; I.049; I.051; I.053; I.058 ; I.066; I.067; I.068 example: acetone 5% by volume emulsion of 10% dimethyl sulfoxide to volume ratio: soybean vivo pachyrhizi (Phakopsora pachyrhizi) (soybean rust) and preventing test solvent Dose: 1µl of Tween ^® 80 per milligram (mg) of active ingredient

The active ingredient is dissolved in a ^{mixture of dimethyl sulfoxide/acetone/Tween ®} 80 and homogenized, and then diluted with water to the desired concentration.

The young soybean plants are treated by spraying the active ingredients prepared as described above. The control plants were only treated with an aqueous solution of acetone/dimethyl sulfoxide/Tween ^{® 80.}

After 24 hours, the leaves were sprayed with an aqueous suspension of Puccinia sojae spores to infect the plants. The infected soybean plants were incubated at 24°C and 100% relative humidity for 24 hours and then at 24°C and 70-80% relative humidity for 10 days.

The test was evaluated 11 days after inoculation. 0% means that the utility is equivalent to the control plant, and 100% means that no disease is observed.

In this test, the following compounds according to the present invention showed an efficacy ranging from 70% to 79% at an active ingredient concentration of 250 ppm: I.016; I.026; I.044; I.046; I.056

In this test, the following compounds according to the present invention showed an efficacy ranging from 80% to 89% at an active ingredient concentration of 250 ppm: I.007; I.021; I.025; I.027; I.032 ; I.040

In this test, the following compounds according to the present invention showed an efficacy ranging from 90% to 100% at an active ingredient concentration of 250 ppm: I.003; I.011; I.022; I.034; I.036 I.037; I.038; I.041; I.042; I.049; I.051; I.053; I.058; I.066; I.067; I.068; I.069; I .070 example: in vitro cell assay solvent rice blast fungus (Pyricularia oryzae): DMSO medium: glucose 14.6 g of anhydrous D- (VWR), 7.1g fungal peptone (Oxoid), 1.4 g granular yeast extract (Merck), QSP 1 liter inoculum: spore suspension

The fungicide is dissolved in DMSO and this solution is used to prepare the required concentration range. The final DMSO concentration used for analysis is ≤1%.

A spore suspension of Magnaporthe grisea was prepared and diluted to the desired spore concentration.

Liquid culture analysis was used to evaluate the fungicide's ability to inhibit spore germination and mycelial growth. The compound is added to the spore-containing medium at the desired concentration. After 5 days of cultivation, the fungal toxicity of the compound was determined by spectroscopic measurement of mycelial growth. The effect of inhibiting the growth of fungi is determined by comparing the absorption value of the wells containing fungicides with the absorption value of the control wells without fungicides.

In this test, the following compounds according to the present invention showed an efficacy ranging from 70% to 79% at an active ingredient concentration of 20 ppm: I.015; I.018; I.022; I.038

In this test, the following compounds according to the present invention showed an efficacy ranging from 80% to 89% at an active ingredient concentration of 20 ppm: I.004; I.006; I.011; I.021; I.040 ; I.052; I.058; I.063

In this test, the following compounds according to the present invention showed an efficacy ranging from 90% to 100% at an active ingredient concentration of 20 ppm: I.003; I.009; I.016; I.019; I.029 ; I.036; I.039; I.043; I.044 ; I.045; I.049; I.067 example: anthrax bean Colletotrichum (Colletotrichum lindemuthanium) bacterial cells in vitro test solvent: DMSO medium: 14.6g anhydrous D-glucose (VWR), 7.1g fungal protein inocula (Oxoid), 1.4g granular yeast extract (Merck), QSP 1 liter inoculum: spore suspension

The fungicide is dissolved in DMSO and this solution is used to prepare the required concentration range. The final DMSO concentration used for analysis is ≤1%.

Prepare a spore suspension of Colletotrichum spinosum from Phaseolus vulgaris and dilute to the desired spore concentration.

Liquid culture analysis was used to evaluate the fungicide's ability to inhibit spore germination and mycelial growth. The compound is added to the spore-containing medium at the desired concentration. After 6 days of cultivation, the fungal toxicity of the compound was determined by spectroscopic measurement of mycelial growth. The effect of inhibiting the growth of fungi is determined by comparing the absorption value of the wells containing fungicides with the absorption value of the control wells without fungicides.

In this test, the following compounds according to the present invention showed an efficacy ranging from 70% to 79% at an active ingredient concentration of 20 ppm: I.001; I.007; I.012; I.031; I.048 ; I.057; I.060; I.070

In this test, the following compounds according to the present invention showed an efficacy ranging from 80% to 89% at an active ingredient concentration of 20 ppm: I.002; I.013; I.015; I.016; I.017 ; I.018; I.023; I.024; I.025; I.026; I.032; I.034; I.037; I.038; I.040; I.042; I.044; I .049; I.061; I.062; I.063; I.069

In this test, the following compounds according to the present invention exhibited effects ranging from 90% to 100% at an active ingredient concentration of 20 ppm: I.003; I.006; I.009; I.011; I.019 ; I.021; I.022; I.029; I.036; I.039; I.041; I.043; I.045; I.046; I.051; I.056; I.058; I .066; I.067; I.068 example: in vivo preventive test solvent pachyrhizi (Phakopsora) (soybean) of test: 24.5 parts by weight of acetone 24.5 parts by weight of dimethyl sulfoxide emulsifier: 1 part by weight Polyethoxyethylene sorbitan monooleate

Mix 1 part by weight of the active compound with the stated amount of solvent and emulsifier to produce a suitable preparation of the active compound, and dilute the concentrate with water to the desired concentration.

Spray the young plants with the preparation of the active compound at the stated application rate to test the preventive effect. After the sprayed layer is dried, the plants are inoculated with an aqueous spore suspension of the pathogen of soybean rust ( Phakopsora pachyrhizi ) , and then left in a non-light incubator at approximately 24°C and 95% relative atmospheric humidity 24h.

The plants are placed in an incubator at approximately 24°C and approximately 80% relative atmospheric humidity with a day/night interval of 12 hours.

The test is evaluated 7 days after inoculation. 0% means that the effect is equivalent to that of the untreated control plant, and 100% means that no disease is observed. Example: pachyrhizi (Phakopsora) live (soybean) Test of in vivo treatment test Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethyl sulfoxide Emulsifier: 1 part by weight of ethylene polyethoxy sorbitan monooleate ester

Mix 1 part by weight of the active compound with the stated amount of solvent and emulsifier to produce a suitable preparation of the active compound, and dilute the concentrate with water to the desired concentration.

Inoculate young plants with an aqueous spore suspension of the pathogen of soybean rust ( Phakopsora pachyrhizi ) , and then leave them in a non-light incubator at approximately 24°C and 95% relative atmospheric humidity for 24 hours for testing and treatment Sexual utility.

The plants are placed in an incubator at approximately 24°C and approximately 80% relative atmospheric humidity with a day/night interval of 12 hours.

Two days after the inoculation, the plants were sprayed with the preparation of active compound at the stated application rate and then left in the incubator.

The test is evaluated 7 days after inoculation. 0% means that the effect is equivalent to that of the untreated control plant, and 100% means that no disease is observed. Example: pachyrhizi (Phakopsora) live (soybean) in vivo test of durability test Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethyl sulfoxide Emulsifier: 1 part by weight of ethylene polyethoxy sorbitan monooleate Acid ester

Mix 1 part by weight of the active compound with the stated amount of solvent and emulsifier to produce a suitable preparation of the active compound, and dilute the concentrate with water to the desired concentration.

The preparation of active compound is sprayed with young plants at the stated application rate to test the persistence effect. After the spray layer has dried, the plants are placed in an incubator at approximately 24°C and approximately 80% relative atmospheric humidity with a day/night interval of 12 hours.

8 days after application, the plants were inoculated with an aqueous spore suspension of the pathogen of soybean rust ( Phakopsora pachyrhizi ) , and then left in a non-light incubator at approximately 24°C and 95% relative atmospheric humidity for 24 hours .

The plants are placed in an incubator at approximately 24°C and approximately 80% relative atmospheric humidity with a day/night interval of 12 hours.

The test is evaluated 7 days after inoculation. 0% means that the effect is equivalent to that of the untreated control plant, and 100% means that no disease is observed.

Claims (15)

A compound of formula (I)

, Where R1 is selected from the group consisting of hydrogen, C ₁ -C ₈ -alkyl, C ₃ -C ₈ -cycloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkynyl , -C ₁ -C ₈ -alkyl-aryl, -C ₁ -C ₈ -alkyl-C ₁ -C ₈ -alkoxy, -Si(C ₁ -C ₈ -alkyl) ₃ , -Si Aryl (C ₁ -C ₈ -alkyl) ₂ , -C ₁ -C ₈ -alkyl -C ₃ -C ₈ -cycloalkyl, aryl, heteroaryl, -C ₁ -C ₈ -alkyl -Heteroaryl, di-C ₁ -C ₈ -alkyl phosphate, -C(=O)R ^a , -C(=O)N(R ^a ) ₂ , -C ₁ -C ₆ -alkyl- OC (= O) R ^a and -C ₁ -C ₆ - alkyl -C (= O) R ^a, wherein R ^a selected from the group consisting of the group consisting of: hydrogen, amino, C ₁ -C ₁₀ - alkoxy Group, C ₁ -C ₆ -haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -haloalkenyl, C ₂ -C ₈ -alkynyl, C ₂ -C ₈ -haloalkynyl, C ₁ -C ₈ - alkoxy, C ₁ -C ₈ - alkoxy, halo, C ₁ -C ₈ - alkyl mercapto _{(sulfanyl), C 1 -C 8} - alkylamino, di - C ₁ -C ₈ -alkylamino, -C ₁ -C ₆ -alkyl-C ₁ -C ₆ -alkoxy, C ₃ -C ₁₀ -carbocyclyl, C ₃ -C ₁₀ -halocarbon cycloalkyl group, a 3- to 10-membered heterocyclyl, aryl, heteroaryl, heterocyclic, aryloxy, and heteroaryloxy, wherein the non-cyclic group R1 or R ^a may be one or more of R1 and wherein ^a cyclic substituent R1 or R ^a group may be a ^C or more R1 substituents; X is hydrogen, fluorine or chlorine atom; m is 0, 1 or 2; Het is a 5-membered heteroaryl ; N is 0, 1, 2, 3 or 4; R2 is a substituent independently selected from the group consisting of halogen, cyano, hydroxyl, sulfhydryl, sulfinyl, sulfonyl, amine , Nitro, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -hydroxyalkyl, C ₁ -C ₆ -cyanoalkyl, C ₁ -C _6- Alkoxy, C ₁ -C ₆ -haloalkoxy, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ -hydroxyalkenyl, C ₂ -C ₆ -cyanoalkenyl, C ₂ -C ₆ -alkynyl, C ₂ -C ₆ -haloalkynyl, C ₂ -C ₆ -Hydroxyalkynyl, C ₂ -C ₆ -cyanoalkynyl, C ₁ -C ₆ -Alkylsulfinyl, pentafluoro-λ ⁶ -sulfinyl, arylsulfinyl, C ₁ -C ₆ -alkylsulfinyl, arylsulfinyl, C ₁ -C ₆ -alkane Sulfonyl, arylsulfonyl, C ₃ -C ₁₀ -carbocyclic group, 3- to 10-membered-heterocyclic group, aryl, heteroaryl, C ₃ -C ₁₀ -carbocyclic group, 3- to 10-member-heterocyclic oxy, aryloxy, heteroaryloxy, -Si(C ₁ -C ₆ -alkyl) ₃ , -C(=O)R ²¹ , -C(=O) OR ²¹ , -C(=O)N(R ²¹ ) ₂ , -C(=O)N(OR ²¹ )R ²¹ , -C(=O)NR ²¹ N(R ²¹ ) ₂ , -C(=S )N(R ²¹ ) ₂ , -C(=NR ²¹ )R ²¹ , -C(=NR ²¹ )N(R ²¹ ) ₂ , -C(=NOR ²¹ )R ²¹ , -N(R ²¹ ) ₂ , -NR ²¹ C(=O)OR ²¹ , -N(OR ²¹ )C(=O)OR ²¹ , -NR ²¹ C(=O)N(R ²¹ ) ₂ , -NR ²¹ C(=O)R ²¹ , -N(OR ²¹ )C(=O)R ²¹ , -NR ²¹ C(=S)R ²¹ , -NR ²¹ C(=S)N(R ²¹ ) ₂ , -NR ²¹ C(=NR ²¹ ) R ²¹ , -OC(=O)R ²¹ , -OC(=O)N(R ²¹ ) ₂ , -NR ²¹ S(=O) ₂ R ²¹ _, -N=CR ²¹ -N(R ²¹ ) ₂ , -S(=O) ₂ R ²¹ , -S(=O) ₂ N(R ²¹ ) ₂ , -P(=O)(OR ²¹ ) ₂ , -OC ₁ -C ₆ -(halo)alkyl- Aryl, -C ₁ -C ₆ -(halo)alkyl-C ₃ -C ₁₀ -carbocyclic group, -C ₁ -C ₆ -(halo)alkyl-OC ₃ -C ₁₀ -carbocyclic group , -C ₁ -C ₆ -(halo)alkyl-3-to 10-member-heterocyclyl, -C ₁ -C ₆ -(halo)alkyl-O-3-to 10-member-hetero Cyclic, -C ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl-heteroaryl, -C ₁ -C ₆ -(halo)alkane Group-heteroaryloxy, -C ₁ -C ₆ -(halo)alkyl-OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-C(=O)R ²¹ , -C _1- C ₆ -(halo)alkyl-C(=O)OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-C(=O)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(Halo)alkyl-C(=O)N (OR ²¹ )R ²¹ , -C ₁ -C ₆ -(halo)alkyl-C(=O)NR ²¹ N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-C (=S)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-C(=NR ²¹ )R ²¹ , -C ₁ -C ₆ -(halo)alkyl-C( =NR ²¹ )N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-C(=NOH)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ C(=O)OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-N(OR ²¹ )C(= O)OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ C(=O)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ C (=O)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-N(OR ²¹ )C(=O)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ C(=S)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ C(=S)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl- NR ²¹ C(=NR ²¹ )R ²¹ , -C ₁ -C ₆ -(halo)alkyl-OC(=O)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-OC(= O)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ S(=O) ₂ R ²¹ _, -C ₁ -C ₆ -(halo)alkyl-N= CR ²¹ -N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-SR ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O)R ²¹ ,- C ₁ -C ₆ -(halo)alkyl-S(=O)OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O) ₂ R ²¹ , -C ₁ -C ₆ -(Halo)alkyl-S(=O) ₂ OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O) ₂ N(R ²¹ ) ₂ and -C ₁ -C ₆ -(Halo)alkyl-P(=O)(OR ²¹ ) ₂ , wherein R ²¹ is independently selected from the group consisting of hydrogen, C ₁ -C ₆ -(halo)alkyl, C ₃ -C ₁₀ -carbocyclyl, 3- to 10-membered-heterocyclic group, aryl, heteroaryl and -C ₁ -C ₆ -(halo)alkyl-aryl, wherein acyclic R2 and R ^{The 21} group may be substituted by one or more R ^22a substituents and the cyclic R2 and R ²¹ groups may be substituted by one or more R ^22c substituents. R ^1a , R ^22a , R1 ^c and R ^22c are independently selected from the following Composition group: halogen atom, nitro group, hydroxyl group, cyano group, carboxyl group, amine group, sulfhydryl group, pentafluoro-λ ⁶ -sulfhydryl, methionyl, carbamate, carbamate, C ₁ -C ₆ -alkyl, C ₃ -C ₇ -cycloalkyl, C ₁ -C ₆ -haloalkyl, C ₃ -C ₈ -halocycloalkyl, C ₂ -C ₆ -(halo) Alkenyl, C ₂ -C ₆ -(halo)alkynyl, C ₁ ‑C ₆ -alkylamino, di-C ₁ ‑C ₆ -alkylamino, -Si(C ₁ -C ₆ -alkane Group) ₃ , C ₁ ‑C ₆ -(halo)alkoxy C ₁ -C ₆ -(halo)alkylsulfanyl, C ₁ -C ₆ -(halo)alkylcarbonyl, C _1- C ₆ -Alkylamine formyl, di-C ₁ -C ₆ -alkylamine formyl, C ₁ -C ₆ -(halo)alkoxycarbonyl, aryloxy, C ₁ ‑C _6- (Halo) alkylcarbonyloxy group, C ₁ -C ₆ -(halo)alkylcarbonylamino group, C ₁ -C ₈ -(halo)alkyl hydrogensulfanyl group, C ₁ -C ₈ -(halo) Group) alkylsulfinyl group, C ₁ -C ₈ -(halo)alkylsulfinyl group, C ₁ -C ₈ -alkylsulfinylamino group, C ₁ ‑C ₈ -haloalkylsulfinyl group Amino group, sulfamoyl group, C ₁ ‑C ₈ -alkyl sulfamoyl group and di-C ₁ ‑C ₈ -alkyl sulfamoyl group; or its salt, N-oxide or solvate: The restriction condition is that Het is not: 3-ethyl-1,2,4-diazol-5-yl; and the restriction condition is that the compound of formula (I) is not: 3-[4-(1-methyl-1H-pyrazol-5-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol , 3-[4-(1H-pyrazol-3-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol, 3-[4-(1H-pyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol, 3-[4-(3,5-Dimethyl-1,2-oxazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-㗁Azole-5-ol, 3-[4-(1,2-oxazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol, 3-[4-(1-ethyl-1H-pyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol , 3-[4-(1-methyl-1H-pyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol , 3-[4-(1-ethyl-1H-pyrazol-5-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol , 3-[4-(2-Chloro-1-methyl-1H-imidazol-5-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole- 5-alcohol, 3-[3-Fluoro-4-(1H-imidazol-1-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol, and Not for 3-[4-(2,5-Dimethyl-1H-pyrrol-1-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole-5 -alcohol. (I) The compound of the formula requested item 1, wherein R1 is selected from the group consisting of the group consisting of: hydrogen, C ₁ -C ₆ - alkyl and -C (= O) R ^a, wherein R ^a is C ₁ -C ₆ - alkyl, wherein the non-cyclic group R1 or R ^a may be an item such as the request substituted. The compound of formula (I) according to claim 1, wherein R1 is a hydrogen atom. The compound of formula (I) according to any one of the preceding claims, wherein Het is selected from the group consisting of furyl, thienyl, pyrrolyl, isoazolyl, isothiazolyl, pyrazolyl, azole Group, thiazolyl, imidazolyl, thiadiazolyl, thiadiazolyl, triazolyl and tetrazolyl. The compound of formula (I) according to any one of the preceding claims, wherein R2 is independently selected from the group consisting of halogen, cyano, hydroxyl, sulfhydryl, amino, C ₁ -C ₆ -alkyl , C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -hydroxyalkyl, C ₁ -C ₆ -cyanoalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -halo Alkoxy, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -haloalkenyl, C _2- C ₆ - alkynyl, C ₂ -C ₆ - haloalkynyl, C ₁ -C ₆ - alkyl mercapto, aryl mercapto, C ₁ -C ₆ - alkylsulfinyl acyl, arylalkylene Sulfonyl, C ₁ -C ₆ -alkylsulfonyl, arylsulfonyl, C ₃ -C ₁₀ -carbocyclyl, 3- to 10-membered-heterocyclic group, aryl, heteroaryl, C ₃ -C ₁₀ -Carboepoxy, 3- to 10-membered-heterocyclic oxy, aryloxy, heteroaryloxy, -C(=O)R ²¹ , -C(=O)OR ²¹ , -C(=O)N(R ²¹ ) ₂ , -C(=O)N(OR ²¹ )R ²¹ , -C(=O)NR ²¹ N(R ²¹ ) ₂ , -C(=S)N( R ²¹ ) ₂ , -C(=NOR ²¹ ) R ²¹ , -N(R ²¹ ) ₂ , -NR ²¹ C(=O)OR ²¹ , -NR ²¹ C(=O)N(R ²¹ ) ₂ ,- NR ²¹ C(=O)R ²¹ , -NR ²¹ C(=S)R ²¹ , -NR ²¹ C(=S)N(R ²¹ ) ₂ , -NR ²¹ C(=NR ²¹ )R ²¹ , -OC (=O)R ²¹ , -OC(=O)N(R ²¹ ) ₂ , -NR ²¹ S(=O) ₂ R ²¹ _, -S(=O) ₂ R ²¹ , -S(=O) ₂ N (R ²¹ ) ₂ , -OC ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl -C ₃ -C ₁₀ -carbocyclyl, -C ₁ -C ₆ -(halo)alkyl-OC ₃ -C ₁₀ -carbocyclyl-C ₁ -C ₆ -(halo)alkyl-3-to 10-membered-heterocyclyl, -C ₁ -C ₆ -(Halo)alkyl-O-3- to 10-membered-heterocyclic group, -C ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(halo) Alkyl-heteroaryl, -C ₁ -C ₆ -(halo)alkyl-heteroaryloxy, -C ₁ -C ₆ -(halo)alkyl -OR ²¹ , -C ₁ -C _6- (Halo)alkyl-C(=O)R ²¹ 、-C ₁ -C ₆ -(Halo)alkyl-C(=O)OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-C(=O)N(R ²¹ ) ₂ , -C ₁ -C ₆ -( Halo)alkyl-C(=O)N(OR ²¹ )R ²¹ , -C ₁ -C ₆ -(halo)alkyl-C(=O)NR ²¹ N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-C(=S)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-N(R ²¹ ) ₂ , -C ₁ -C ₆ -(Halo)alkyl-NR ²¹ C(=O)OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ C(=O)N(R ²¹ ) ₂ , -C _1- C ₆ -(halo)alkyl-NR ²¹ C(=O)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ C(=S)R ²¹ , -C ₁ -C ₆ -(Halo)alkyl-NR ²¹ C(=S)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-OC(=O)R ²¹ , -C ₁ -C ₆ -(Halo)alkyl-OC(=O)N(R ²¹ ) ₂ , -C ₁ -C ₆ -(halo)alkyl-NR ²¹ S(=O) ₂ R ²¹ , -C ₁ -C ₆ -(halo)alkyl-SR ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O)R ²¹ , -C ₁ -C ₆ -(halo)alkyl-S( =O)OR ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O) ₂ R ²¹ , -C ₁ -C ₆ -(halo)alkyl-S(=O) ₂ OR ²¹ and -C ₁ -C ₆ -(halo)alkyl-S(=O) ₂ N(R ²¹ ) ₂ , wherein R ²¹ is as described in claim 1 and wherein the acyclic R2 and R ²¹ groups and The cyclic R2 and R ²¹ groups may be substituted as described in claim 1. The compound of formula (I) according to any one of the preceding claims, wherein R2 is independently selected from the group consisting of halogen, cyano, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkane Group, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylamino, di-C ₁ -C ₆ -alkylamino, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -Alkynyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ -haloalkynyl, C ₁ -C ₆ -alkylsulfanyl, C ₃ -C ₁₀ -carbocyclyl, aryl, hetero Aryl, -C(=O)R ²¹ , -C(=O)OR ²¹ , -N(R ²¹ ) ₂ , -OC ₁ -C ₆ -(halo)alkyl-aryl, -C _1- C ₆ -(halo)alkyl-C ₃ -C ₁₀ -carbocyclyl, -C ₁ -C ₆ -(halo)alkyl-3- to 10-membered-heterocyclyl, -C ₁ -C ₆ -(Halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl-heteroaryl, -C ₁ -C ₆ -(halo)alkyl-OR ²¹ and -C ₁ -C ₆ -(halo)alkyl-C(=O)OR ²¹ , wherein R ²¹ is as described in claim 1 and wherein the acyclic or cyclic R2 and R ²¹ groups can be as described in claim 1 The statement is replaced. A compound of formula (I) according to any one of the preceding claims, wherein m is 0 or 1. The compound of formula (I) according to any one of the preceding claims, wherein X is a fluorine atom. A compound of formula (I) according to any one of the preceding claims, wherein n is 0, 1, or 2. A compound of formula (I) according to any one of the preceding claims, wherein Het is selected from the group consisting of: furanyl, thienyl, pyrrolyl, isoazolyl, isothiazolyl, pyrazolyl, azolyl, thiazolyl, thiadiazolyl, thiadiazolyl, three Azolyl and tetrazolyl, and Excluding compounds where R1 is H, X is F, Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present) is methyl or ethyl. The compound of formula (I) according to claim 10, which excludes compounds in which Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present) is C ₁ -C ₆ -alkyl. The compound of formula (I) according to any one of the preceding claims, wherein n is 1, 2, 3 or 4, preferably 1 or 2, and Het is selected from the group consisting of furyl, thienyl, pyrrole Group, isothiazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, triazolyl and tetrazolyl, and R2 is independently selected from the following Group: halogen, cyano, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylamino, di- C ₁ -C ₆ -alkylamino, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ -haloalkynyl, C ₁ -C ₆ -alkylsulfanyl, C ₃ -C ₁₀ -carbocyclyl, aryl, heteroaryl, -C(=O)R ²¹ , -C(=O)OR ²¹ , -N(R ²¹ ) ₂ , -OC ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl -C ₃ -C ₁₀ -carbocyclic group, -C ₁ -C ₆ -(Halo)alkyl-3- to 10-membered-heterocyclyl, -C ₁ -C ₆ -(halo)alkyl-aryl, -C ₁ -C ₆ -(halo)alkyl -Heteroaryl, -C ₁ -C ₆ -(halo)alkyl-OR ²¹ and -C ₁ -C ₆ -(halo)alkyl-C(=O)OR ²¹ , where R ²¹ is as requested As described in item 1 and wherein the acyclic or cyclic R2 and R ²¹ groups may be substituted as described in claim 1. A composition comprising at least one compound of formula (I) according to any one of the preceding claims and at least one agriculturally acceptable carrier. A use of the compound of formula (I) according to any one of claims 1 to 12 or the composition according to claim 13 for controlling phytopathogenic fungi on plants. A method for controlling phytopathogenic fungi, the method comprising administering at least one compound of formula (I) according to any one of claims 1 to 12 or a composition according to claim 13 to plants, plant parts, seeds , The step of the soil in which the fruit or plant grows.