TW201307317A - Novel microbiocides - Google Patents

Abstract

The present invention provides compounds of formula (I) wherein A1, A2, R1, D1, D2, Y3 and X are as defined in the claims. The invention further relates to compositions which comprise these compounds and to their use in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.

Description

New microbicide

The invention relates to novel microbicidal active purine derivatives (particularly fungicidal activity). It is further related to the intermediates used in the preparation of these compounds, as well as the compositions comprising these compounds, and their use in agriculture or horticulture as a means of controlling or preventing plant parasitis caused by phytopathogenic microorganisms, preferably fungi. The use of pests is related.

The fungicidal activity biguanide has been described in WO08074418.

Surprisingly, it has been found that the novel anthraquinone derivatives possess microbicidal activity.

The invention is relatively related to the anthracene derivative of formula (I)

Or a salt or N-oxide thereof, wherein R ¹ represents hydrogen, halogen, CN, SH, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfinyl, C ₁ -C _8- alkylsulfonyl, NH ₂ , C ₁ -C ₁₀ alkyl, C ₃ -C ₈ cycloalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl, (R ⁷ O)carbonyl ( C ₁ -C ₄ alkyl), phenyl or pyridyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and pyridyl groups can be independently selected from one or more of the following groups: Alternative substitution: halogen, CN, NH ₂ , NH-C ₁ -C ₈ alkyl, N(C ₁ -C ₈ alkyl) ₂ , NO ₂ , OR ⁷ , C ₁ -C ₄ alkyl, C ₁ - a C ₄ haloalkyl group, a C ₃ -C ₆ cycloalkyl group, and a 5- or 6-membered heterocyclic ring (containing one to three heteroatoms independently selected from O, S and N, provided that the heterocyclic ring does not comprise a phase An adjacent oxygen atom, an adjacent sulfur atom, or an adjacent sulfur and oxygen atom; A ² represents a G-1 ring:

D ¹ represents N or CY ¹ ; D ² represents N or CY ² ; wherein D ¹ and D ² cannot both be N; D ³ represents N or CR ⁶ ; D ⁴ represents N or CR ⁵ ; wherein D ³ and D ⁴ cannot All are N; each independently R ² , R ⁴ , R ⁵ and R ⁶ represent hydrogen, halogen, CN, NO ₂ , C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₂ -C ₈ Alkenyl, C ₂ -C ₈ alkynyl, phenyl, 5- or 6-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S and N, provided that the heterocycle does not contain adjacent Oxygen atom, adjacent sulfur atom, or adjacent sulfur and oxygen atom), COR ⁸ , OR ⁷ , SH, C ₁ -C ₈ alkylthio group, C ₁ -C ₈ alkyl sulfinylene group , C ₁ -C ₈ alkylsulfonyl, phenylthio, phenylsulfinylene, phenylsulfonyl, N(R ⁹ ) ₂ , CO ₂ R ⁷ , O(CO)R ⁸ , CON( R ⁹ ) ₂ , NR ⁹ COR ⁸ or CR ⁸ N-OR ⁷ , wherein alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and heterocyclic may be or may be derived from halogen, CN, NH ₂ , NO ₂ a group independently selected from OR ⁷ , C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, or R ⁴ and R ⁵ , R ⁵ and R ² , or R ⁶ pyridine and R ² together with ring segment connected to it, or Can be formed partially or fully unsaturated 5- to 7-membered carbocyclic ring, or a partially or fully unsaturated 5- to 7-membered heterocyclic ring (containing from one to three O, S, N and N (R ⁹⁾ independently a hetero atom selected, provided that the heterocyclic ring does not contain an adjacent oxygen atom, an adjacent sulfur atom, or an adjacent sulfur and oxygen atom), and wherein R ⁴ and R ⁵ , R ⁵ and R ² or a ring formed by R ⁶ and R ² may be one or more selected from the group consisting of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ The alkoxy group is optionally substituted with a group independently selected from a C ₁ -C ₄ haloalkoxy group; X represents X-2, X-3, X-4 or X-5:

The respective independent Z ¹ , Z ² , Z ³ , Z ⁵ , Z ⁶ , Z ⁷ , Z ⁸ , Z ⁹ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ represent CR ¹⁰ R ¹¹ , C=O or C= CR ¹² R ¹³ ; Z ⁴ and Z ¹² represent CR ¹⁴ R ¹⁵ , SiR ¹⁶ R ¹⁷ , C=O or C=CR ¹² R ¹³ ; or in each case, two adjacent radicals Z ⁴ and Z ⁵ Or Z ⁷ with Z ⁸ or Z ⁸ with Z ⁹ or Z ¹¹ with Z ¹² or Z ¹² with Z ¹³ or Z ¹³ with Z ¹⁴ , possibly together representing from CR ¹⁰ =CR ¹¹ - and -C≡C- Selected groups wherein X-4 or X-5 may not contain more than one such group; each individually independent R ¹⁰ and R ¹¹ represents hydrogen, halogen, CN, OH, C ₁ -C ₄ alkane a C ₁ -C ₄ haloalkyl or phenyl group wherein the phenyl group is derived from one or more of halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ The alkoxy group and the C ₁ -C ₄ haloalkoxy group independently selected are selectively substituted; or R ¹⁰ and R ¹¹ together with the carbon atom to which they are attached may form a C ₃ -C ₆ ring Alkyl or C ₃ -C ₆ halocycloalkyl; each individually independent R ¹² and R ¹³ represent hydrogen, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl; each individually independent R ^14, R ^15, R ¹⁶ and R ¹⁷ TABLE hydrogen, _{halogen, CN, OH, C 1 -C} 4 alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or phenyl, wherein the phenyl group is one or more selected from halogen, a group independently selected from CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy; Or R ¹⁴ and R ¹⁵ together with the carbon atom to which they are attached may form a C ₃ -C ₆ cycloalkyl group or a C ₃ -C ₆ halocycloalkyl group; wherein the groups X-2, X-3, X- 4 X-5 and contain at most one ring, which comprises only three groups of Z ¹ to Z ¹⁴ in a group, or a group Z ¹ to Z two ^14-yl, or a group Z ¹ to Z ¹⁴ group Or four of the radicals Z ¹ to Z ¹⁴ as ring members; and wherein Z ¹ , Z ³ , Z ⁶ and Z ¹⁰ groups are not substituted by OH; and wherein Z ¹ , Z ² , Z ³ , Z ⁴ , Z ⁵ , Z ⁶ , Z ⁷ , Z ⁸ , Z ⁹ , Z ¹⁰ , Z ¹¹ , Z ¹² , Z ¹³ and Z ¹⁴ none of the carbon atoms substituted by two OH; independent Y ¹ , Y ² and Y ³ represent hydrogen, halogen, CN, NO ₂ , C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl, Phenyl, 5- or 6-membered heterocyclic ring (containing one to From O, S and N heteroatoms independently selected, and the conditions for the heterocyclic ring does not contain adjacent oxygen atoms, adjacent sulfur atom, a sulfur or oxygen atom adjacent ^{to), COR 8, OR 7,} SH , C ₁ -C ₈ alkylthio group, C ₁ -C ₈ alkylsulfinyl group, C ₁ -C ₈ alkylsulfonyl group, phenylthio group, phenylsulfinylene group, phenylsulfonate a group, N(R ⁹ ) ₂ , CO ₂ R ⁷ , O(CO)R ⁸ , CON(R ⁹ ) ₂ , NR ⁹ COR ⁸ or CR ⁸ N-OR ⁷ , wherein alkyl, cycloalkyl, alkenyl , alkynyl, phenyl and heterocyclic ring may be independently selected from one or more of halogen, CN, NH ₂ , NO ₂ , OR ⁷ , C ₁ -C ₄ alkyl and C ₁ -C ₄ haloalkyl Selectively substituted; or Y ¹ and Y ³ or Y ² and Y ³ together with the pyridine ring segment attached thereto, may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring, or a portion Or a fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, N and N(R ⁹ ), provided that the heterocyclic ring does not contain an adjacent oxygen atom, An adjacent sulfur atom, or an adjacent sulfur and oxygen atom), and wherein the ring formed by Y ¹ and Y ³ or Y ² and Y ³ may be a ring Or a plurality of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy The independently selected groups are optionally substituted; A ¹ represents ring A-1, A-2, A-3, A-4, A-5, A-6 or A-7:

Individually independent R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ and R ²² represent hydrogen, halogen, CN, NO ₂ , C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₂ -C ₈ olefin a C ₂ -C ₈ alkynyl group, a phenyl group, a 5- or 6-membered heterocyclic ring (containing one to three heteroatoms independently selected from O, S and N, provided that the heterocyclic ring does not contain adjacent Oxygen atom, adjacent sulfur atom, or adjacent sulfur and oxygen atom), benzyl, COR ⁸ , OR ⁷ , SH, C ₁ -C ₈ alkylthio group, C ₁ -C ₈ alkylsulfin Sulfhydryl, C ₁ -C ₈ alkylsulfonyl, phenylthio, phenylsulfinylene, phenylsulfonyl, N(R ⁹ ) ₂ , CO ₂ R ⁷ , O(CO)R ⁸ , CON(R ⁹ ) ₂ , NR ⁹ COR ⁸ or CR ⁸ N-OR ⁷ , wherein alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, heterocyclic and benzyl may be one or more from halogen, CN a group independently selected from NH ₂ , NO ₂ , OR ⁷ , C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, or R ¹⁸ and R ²¹ , R ¹⁸ and R ²² , or R ²⁰ and R ²¹ together with the fragment of the ring to which it is attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring, or a partially or fully unsaturated 5- to 7-membered ring. Heterocycle Containing one to three heteroatoms independently selected from O, S, N and N(R ⁹ ), provided that the heterocycle does not contain adjacent oxygen atoms, adjacent sulfur atoms, or adjacent sulfur and oxygen atoms And wherein the ring formed by R ¹⁸ and R ²¹ , R ¹⁸ and R ²² or R ²⁰ and R ²¹ may be derived from one or more of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ a group independently selected from an alkyl group, a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₄ alkoxy group and a C ₁ -C ₄ haloalkoxy group; when A ¹ is A-1 Moreover, D ¹ is CY ¹ , and R ²² and Y ¹ together with the fragment to which it is attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring, or partially or fully unsaturated 5- to 7- a heterocyclic ring (containing one to three heteroatoms independently selected from O, S, N and N(R ⁹ ), provided that the heterocyclic ring does not contain adjacent oxygen atoms, adjacent sulfur atoms, or adjacent Sulfur and oxygen atoms), and wherein the ring formed by R ²² and Y ¹ may be derived from one or more of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ alkylthio group are independently selected The resulting group is optionally substituted; each independently R ⁷ represents hydrogen, C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ Alkynyl, C ₁ -C ₄ alkylsulfonyl, phenyl, benzyl or 5- or 6-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S and N, provided that the hetero The ring does not contain adjacent oxygen atoms, adjacent sulfur atoms, or adjacent sulfur and oxygen atoms), wherein alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and heterocyclic rings are One or more from halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ halo Selective groups selected independently of oxy, C ₁ -C ₄ -alkyl-C ₁ -C ₄ -alkoxy and C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl Substituted; each individually independent R ⁸ represents hydrogen, C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl, phenyl, benzyl Or pyridyl, wherein alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl, pyridyl is derived from one or more of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C _4- alkyl, C ₁ -C ₄ halide a group independently selected from an alkyl group, a C ₁ -C ₄ alkoxy group and a C ₁ -C ₄ haloalkoxy group; each individually independent R ⁹ represents hydrogen, OH, C ₁ -C _8- alkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl or COR ⁸ Wherein alkyl, alkoxy, alkenyl and alkynyl are optionally substituted by more than one halogen; wherein when two R ⁹ groups are attached to the same nitrogen atom, these groups may be the same or different Wherein when two R ⁹ groups are attached to the same nitrogen atom, the two groups cannot be OH, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy; wherein when two R ⁹ When the same nitrogen atom is attached to the same, the two groups together with the nitrogen atom to which they are attached may form rings B-1, B-2, B-3, B-4, B-5, B-6, B-7 or B-8:

The ring formed therein is derived from halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C More than one independently selected one of the ₄ haloalkoxy groups is selectively substituted.

The present invention encompasses all agronomically acceptable salts, isomers, structural isomers, stereoisomers, diastereomers, mirror image isomers, tautomers, and spin pairs of such compounds. Opposite and N-oxide. The compounds of formula I may be present in different geometric isomers or optical isomers or in different tautomeric forms. One or more chiral centers may be present, in which case the compound of formula I may be in the form of a pure mirror image isomer, a mixture of mirror image isomers, a pure non-image isomer or a mixture of non-spiegel isomers. presence. A double bond may be present in the molecule, such as a C=C or C=N bond, in which case the compound of Formula I may exist as a single isomer or a mixture of isomers. There may be a center of tautomerization. The present invention includes all such isomers and tautomers, as well as mixtures thereof in various ratios, as well as isotopic forms, such as compounds containing heavy hydrogen. In addition, rotational enantiomerism may occur due to limited rotation of a single bond.

Halogen, whether as a sole substituent or in combination with another substituent (e.g., haloalkyl), is typically fluorine, chlorine, bromine or iodine, and is typically fluorine, chlorine or bromine.

Each alkyl moiety (including an alkyl moiety of an alkoxy group, alkylthio group, etc.) is straight or branched and depends on the number of carbon atoms it contains, such as methyl, ethyl, N-propyl, n-butyl, n-pentyl, n-hexyl, isopropyl, sec-butyl, isobutyl, tert-butyl, neopentyl, n-heptyl, or 1,3-dimethylbutyl, Also usually it is methyl or ethyl.

The alkenyl and alkynyl groups may be mono- or di-unsaturated and are examples of the alkyl groups described above.

The haloalkyl moiety is an alkyl moiety substituted by one or more of the same or different halogen atoms, for example, monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, dichloromethyl, trichloro Methyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 1-fluoroethyl, 2-chloroethyl, Pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl, typically Trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichlorofluoromethyl.

Alkoxy, for example, is methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy, and is usually Methoxy or ethoxy.

Haloalkoxy, for example, is fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoro Ethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy, and usually difluoromethoxy, 2 - chloroethoxy and trifluoromethoxy.

The alkylthio group, for example, is methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, and Usually it is methylthio or ethylthio.

Alkylsulfonyl, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl , sec-butylsulfonyl or tert-butylsulfonyl, and usually methylsulfonyl or ethylsulfonyl.

The alkylsulfinylene group, for example, is a methylsulfinylene group, an ethylsulfinyl group, a propylsulfinylene group, an isopropylsulfinyl group, a n-butylsulfinylene group, Isobutylsulfinylene, sec-butylsulfinylene or tert-butylsulfinylene, and usually methylsulfinyl or ethylsulfinylene.

The cycloalkyl group may be saturated or partially unsaturated, preferably fully saturated, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

Alkoxyalkyl, for example, is methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, Isopropoxymethyl or isopropoxyethyl.

Aryl groups include phenyl, naphthyl, anthracenyl, fluorenyl and indanyl, but are typically phenyl.

Carbocycles include cycloalkyl and aryl groups.

The heterocycloalkyl group is a non-aromatic ring which may be saturated or partially saturated, preferably fully saturated, and contains a carbon atom as a ring member and at least one hetero atom selected from a ring element of O, S and N. Examples include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, 1,3-dioxolyl, 1,4-dioxanyl, aziridine, Azetidinyl, pyrrolidinyl, piperidinyl, 吖 Base, morpholinyl, thiomorpholinyl, imidazolidinyl, pyrazolidinyl and piperidin Base, preferably morpholinyl, pyrrolidinyl, piperidinyl and piperidine Base, and more preferably morpholinyl and pyrrolidinyl.

The heterocyclic aryl group, for example, is a monovalent monocyclic or bicyclic aromatic hydrocarbon group. Examples of monocyclic groups include pyridyl, pyridazinyl, pyrimidinyl, pyridyl Base, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furyl, phenylthio, Azolyl, different Azolyl, oxadiazolyl, thiazolyl, isothiazolyl and thiadiazolyl. Examples of bicyclic groups include quinolyl, porphyrin, quin A phenyl group, a benzimidazolyl group, a benzothienyl group and a benzothiadiazolyl group. Preferred are monocyclic heterocyclic aryl groups, especially pyridyl, pyrrolyl, imidazolyl and triazolyl groups, such as 1,2,4triazolyl, pyridyl and imidazolyl are the most preferred.

The terms "heterocycle" and "heterocyclic ring" are used interchangeably and are defined to include heterocycloalkyl and heterocyclic aryl. Any reference herein to a heterocyclic ring refers primarily to the specific examples listed above in the definitions of heterocyclic aryl and heterocycloalkyl, and preferably morpholinyl, pyrrolidinyl, piperidinyl, piperidine A pyridyl group, a pyrrolyl group, an imidazolyl group and a triazolyl group, for example, a 1,2,4triazolyl group, more preferably a morpholinyl group, a pyrrolidinyl group, a pyridyl group and an imidazolyl group. No heterocycle contains an adjacent oxygen atom, an adjacent sulfur atom, or an adjacent oxygen and sulfur atom.

When a moiety is indicated as being (optionally) substituted, such as an alkyl group, this includes those moieties belonging to a larger group, such as an alkyl group within an alkylthio group. The same principle applies to, for example, a phenyl group among phenylthio groups and the like. When a portion of this is indicated to be optionally substituted by more than one other group, it is preferred to have one to five optional substituents, and more preferably one to three substituents. One of the moieties is substituted by a cyclic group such as an aryl group, a heteroaryl group, a cycloalkyl group, preferably not more than two such substituents, and more preferably no more than one such substituent.

The following substituent definitions (including preferred definitions) can be combined in any combination: R ¹ represents hydrogen, halogen, CN, SH, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkyl Thiol group, C ₁ -C ₈ alkylsulfonyl group, NH ₂ , C ₁ -C ₁₀ alkyl group, C ₃ -C ₈ cycloalkyl group, C ₂ -C ₈ alkenyl group, C ₂ -C ₈ alkynyl group (R ⁷ O)carbonyl (C ₁ -C ₄ alkyl), phenyl or pyridyl, wherein alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and pyridyl can be from one or more of the following Selective substitutions among independently selected groups (eg one to five): halogen, CN, NH ₂ , NH-C ₁ -C ₈ alkyl, N(C ₁ -C ₈ alkyl) ₂ , NO ₂ , OR ⁷ , C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl, and 5- or 6-membered heterocyclic ring (containing one to three independently selected from O, S and N) A heteroatom, provided that the heterocycle does not contain an adjacent oxygen atom, an adjacent sulfur atom, or an adjacent sulfur and oxygen atom). Heterocycles are preferably as defined herein, especially morpholinyl, pyrrolidinyl, piperidinyl, piperidine A pyridyl group, a pyrrolyl group, an imidazolyl group or a triazolyl group, for example, a 1,2,4triazolyl group, more preferably a morpholinyl group, a pyrrolidinyl group, a pyridyl group or an imidazolyl group.

Preferably, R ¹ represents hydrogen, C ₁ -C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl, C ₃ -C ₈ cycloalkyl, phenyl, pyridyl or R ⁷ O)carbonyl (C ₁ -C ₄ alkyl) wherein alkyl, alkenyl, alkynyl, cycloalkyl, phenyl and pyridyl may be derived from one or more (eg one to five) from halogen, CN, OR ⁷ , NH ₂ , NH-C ₁ -C ₈ alkyl, N(C ₁ -C ₈ alkyl) ₂ , C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ A group independently selected from a cycloalkyl group and a pyridyl group is optionally substituted.

More preferably, R ¹ represents hydrogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, phenyl or pyridyl, wherein alkyl, alkenyl, phenyl and pyridyl may be one or more ( For example, one to five) from halogen, CN, OH, NH ₂ , NH-C ₁ -C ₄ alkyl, N(C ₁ -C ₄ alkyl) ₂ , C ₁ -C ₄ alkyl, C ₁ -C ₄ A group independently selected from a haloalkyl group, a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ haloalkoxy group and a C ₃ -C ₆ cycloalkyl group is optionally substituted.

More preferably, R ¹ represents hydrogen or C ₁ -C ₄ alkyl.

More preferably, R ¹ represents a C ₁ -C ₄ alkyl group.

In a preferred group of compounds, R ¹ represents C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, phenyl or pyridyl, wherein alkyl, alkenyl, phenyl and pyridyl may be one or A plurality (for example, one to five) are selectively substituted from a group independently selected from a halogen, a CN, a C ₁ -C ₄ alkoxy group and a C ₁ -C ₄ haloalkoxy group.

In another preferred group of compounds, R ¹ represents hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, phenyl or pyridin-2-yl, wherein phenyl and pyridin-2- The group may be optionally substituted by one or more (e.g., one to five) groups independently selected from halogen, CN, methyl, halomethyl, methoxy, and halomethoxy.

In another preferred group of compounds, R ¹ represents hydrogen, C ₁ -C ₄ alkyl or C ₂ -C ₄ alkenyl, wherein alkyl and alkenyl may be derived from one or more (eg, one to five) The groups independently selected from halogen, CN, methoxy and halomethoxy are optionally substituted.

D ¹ represents N or CY ¹ ; D ² represents N or CY ² ; wherein D ¹ and D ² cannot both be N.

Preferably, D ¹ represents N or CY ¹ ; D ² represents CY ² .

More preferably, D ¹ represents CY ¹ ; D ² represents CY ² .

D ³ represents N or CR ⁶ ; D ⁴ represents N or CR ⁵ ; wherein D ³ and D ⁴ cannot both be N.

Preferably, D ³ represents N or CR ⁶ ; D ⁴ represents CR ⁵ .

More preferably, D ³ represents CR ⁶ ; D ⁴ represents CR ⁵ .

In one group of compounds, D ¹ is N and D ² is CY ² .

In another group of compounds, D ¹ is CY ¹ and D ² is N.

In another group of compounds, D ¹ is CY ¹ and D ² is CY ² .

In one group of compounds, D ³ is N and D ⁴ is CR ⁵ .

In another group of compounds, D ³ is CR ⁶ and D ⁴ is N.

In another group of compounds, D ³ is CR ⁶ and D ⁴ is CR ⁵ .

In one group of compounds, D ¹ and D ³ are N; D ² is CY ² ; D ⁴ is CY ⁴ .

In another group of compounds, D ¹ is N; D ² is CY ² ; D ³ is CY ³ ; D ⁴ is CY ⁴ .

In another group of compounds, D ¹ is CY ¹ ; D ² is CY ² ; D ³ is N; D ⁴ is CY ⁴ .

In a better group of compounds, D ¹ is CY ¹ ; D ² is CY ² ; D ³ is CY ³ ; D ⁴ is CY ⁴ .

Each independently R ² , R ⁴ , R ⁵ and R ⁶ represent hydrogen, halogen, CN, NO ₂ , C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₂ -C ₈ alkenyl, C _{a 2-} C ₈ alkynyl group, a phenyl group, a 5- or 6-membered heterocyclic ring (containing one to three heteroatoms independently selected from O, S and N, provided that the heterocyclic ring does not contain an adjacent oxygen atom, Adjacent sulfur atom, or adjacent sulfur and oxygen atom (for example: heterocyclic ring as defined herein, preferably morpholinyl, pyrrolidinyl, piperidinyl, piperidine Or pyridyl, pyrrolyl, imidazolyl or triazolyl, for example: 1,2,4 triazolyl, more preferably morpholinyl, pyrrolidinyl, pyridyl or imidazolyl), COR ⁸ , OR ⁷ , SH, C ₁ -C ₈ alkylthio group, C ₁ -C ₈ alkylsulfinyl group, C ₁ -C ₈ alkylsulfonyl group, phenylthio group, phenyl sulfinylene group, Phenylsulfonyl, N(R ⁹ ) ₂ , CO ₂ R ⁷ , O(CO)R ⁸ , CON(R ⁹ ) ₂ , NR ⁹ COR ⁸ or CR ⁸ N-OR ⁷ , wherein alkyl, naphthenic The base, alkenyl, alkynyl, phenyl and heterocyclic ring may be one or more (for example one to five) from halogen, CN, NH ₂ , NO ₂ , OR ⁷ , C ₁ -C ₄ alkyl, C ₁ -C _The groups independently selected by the ₄ haloalkyl group may be selectively substituted; or R ⁴ and R ⁵ , R ⁵ and R ² , or R ⁶ and R ² together with the pyridine ring segment attached thereto may form Partially or completely unsaturated 5- to 7-membered carbocyclic ring, or partially or fully unsaturated 5- to 7-membered heterocyclic ring (containing one to three independently selected from O, S, N and N(R ⁹ ) a hetero atom, provided that the heterocyclic ring does not contain an adjacent oxygen atom, an adjacent sulfur atom, or an adjacent sulfur and oxygen atom (eg, R ⁴ and R ⁵ , R ⁵ and R ² , or R ⁶ together with R ² and the pyridyl ring fragment to which they are attached may be formed by isoquinoline; 5,6,7,8-tetrahydro-isoquinoline; 6,7-dihydro- 5H-[2]pyridine; 3,4-dihydro-1H-pyrano[3,4-c]pyridine; 6,7,8,9-tetrahydro-5H-cycloheptane[ c] pyridine; [1,7]naphthyridine; quinoline; 5,6,7,8-tetrahydro-quinoline; 6,7-dihydro-5H-[1]azepine, [1,8]naphthalene a cyclized ring system selected from 7,8-dihydro-5H-pyrano[4,3-b]pyridine; These ring systems are illustrated below), and wherein the ring formed by R ⁴ and R ⁵ , R ⁵ and R ² or R ⁶ and R ² may be one or more (for example one to five) Independent of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy The selected groups are selectively substituted.

Preferably, each independently R ² , R ⁴ , R ⁵ and R ⁶ represent hydrogen, halogen, CN, OR ⁷ , C ₁ -C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₃ -C ₈ Cycloalkyl, phenyl, pyridyl, N(R ⁹ ) ₂ , CO ₂ R ⁷ , NR ⁹ COR ⁸ , SH, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkyl sulfoxide a C ₁ -C ₈ alkylsulfonyl group, a phenylthio group, a phenylsulfinylene group or a phenylsulfonyl group, wherein the alkyl group, the alkenyl group, the cycloalkyl group, the phenyl group and the pyridyl group may be one or more Selectively substituted (for example one to five) from a halogen, CN, OR ⁷ , C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl group; or R ⁴ and R ⁵ , R ⁵ and R ² , or R ⁶ and R ² together with the pyridine ring segment attached thereto, may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring, or partially or fully unsaturated 5- to 7 a heterocyclic ring (containing one to three heteroatoms independently selected from O, S, N and N(R ⁹ ), provided that the heterocyclic ring does not contain an adjacent oxygen atom, an adjacent sulfur atom, or a phase o sulfur and oxygen atom, (e.g.: R ⁴ and R ^5, R ⁵ and R ^2, or R ⁶ and R ² together with their ring segment connected pyridinyl, might be able to form From isoquinoline; 5,6,7,8-tetrahydro-isoquinoline; 6,7-dihydro-5H-[2]azepine; 3,4-dihydro-1H-pyrano[3, 4-c]pyridine; 6,7,8,9-tetrahydro-5H-cyclohepta[c]pyridine; [1,7]naphthyridine; quinoline; 5,6,7,8-tetrahydro- Quinoline; 6,7-dihydro-5H-[1]azepine, [1,8]naphthyridine; 6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine; , a ring system selected by 8-dihydro-5H-pyrano[4,3-b]pyridine)), and wherein R ⁴ and R ⁵ , R ⁵ and R ² or R ⁶ and R ² are formed. a ring, which may be one or more (for example one to five) from halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ halo The groups independently selected from the alkoxy group are selectively substituted.

More preferably, each independently R ² , R ⁴ , R ⁵ and R ⁶ represent hydrogen, halogen, OR ⁷ , CN, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, N(R ⁹ ) ₂ , phenyl, CO ₂ R ⁷ or NR ⁹ COR ⁸ , wherein the alkyl group, the cycloalkyl group and the phenyl group may be one or more (for example one to five) from halogen, CN, C ₁ -C ₄ alkyl a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ haloalkoxy group independently selected from a group; or R ⁴ and R ⁵ , R ⁵ and R ² , or R ⁶ and R ² together with the pyridyl ring segment attached thereto, may form a fully or partially unsaturated 5- or 6-membered carbocyclic ring (eg, R ⁴ and R ⁵ , R ⁵ and R ² , or R ⁶ and R ² together with the pyridyl ring fragment attached thereto may form from isoquinoline; 5,6,7,8-tetrahydro-isoquinoline; quinoline; and 5,6,7,8- The ring system selected by tetrahydro-quinoline) can be optionally substituted by one or more (e.g., one to five) groups independently selected from the group consisting of halogen, methyl and halomethyl.

More preferably, each independently R ² , R ⁴ , R ⁵ and R ⁶ represent hydrogen, halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ cycloalkyl, N(R ⁹ ) ₂ , phenyl or CO ₂ R ⁷ wherein alkyl, alkoxy, alkenyloxy, cycloalkyl and phenyl may be one or Multiple (for example one to five) independent of halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy The selected group is optionally substituted; or R ⁴ and R ⁵ , R ⁵ and R ² , or R ⁶ and R ² together with the pyridyl ring segment attached thereto may form a complete or partial unsaturated 6- a carbocyclic ring (eg, R ⁴ and R ⁵ , R ⁵ and R ² , or R ⁶ and R ² together with a pyridyl ring segment attached thereto, may form from isoquinoline; ⁵ , ⁶ , ⁷ , ^{8 -} 4 Hydrogen-isoquinoline; quinoline; ring system selected with 5,6,7,8-tetrahydro-quinoline), which may be derived from one or more (eg one to five) from halogen, methyl and halogen The groups independently selected by the methyl group are selectively substituted.

More preferably, each independently R ² , R ⁴ , R ⁵ and R ⁶ represent hydrogen, C ₁ -C ₄ alkyl, CN or C ₁ -C ₄ alkoxy, wherein alkyl and alkoxy are One or more (e.g., one to five) groups independently selected from halogen, CN, C ₁ -C ₄ alkyl, and C ₁ -C ₄ haloalkoxy are optionally substituted.

More preferably, each independently R ² , R ⁴ , R ⁵ and R ⁶ represent hydrogen, C ₁ -C ₄ alkyl or C ₂ -C ₄ alkenyl, wherein the alkyl group and the alkenyl group may be one or more (e.g., one to five) are selectively substituted from a group independently selected from halogen, CN, methoxy, and halomethoxy.

In a group of compounds, each independently R ² , R ⁵ and R ⁶ represent hydrogen or C ₁ -C ₄ alkyl.

In this group of compounds, R ⁴ preferably represents hydrogen or C ₁ -C ₄ alkyl. More preferably, R ⁴ represents a C ₁ -C ₄ alkyl group, and most preferably a methyl group.

X represents X-2, X-3, X-4 or X-5.

Preferably, X represents X-3 or X-5.

Even better, X stands for X-3.

The respective independent Z ¹ , Z ² , Z ³ , Z ⁵ , Z ⁶ , Z ⁷ , Z ⁸ , Z ⁹ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ represent CR ¹⁰ R ¹¹ , C=O or C= CR ¹² R ¹³ ; preferably CR ¹⁰ R ¹¹ or C=CR ¹² R ¹³ ; more preferably CR ¹⁰ R ¹¹ .

Z ⁴ and Z ¹² represent CR ¹⁴ R ¹⁵ , SiR ¹⁶ R ¹⁷ , C=O or C=CR ¹² R ¹³ ; preferably CR ¹⁴ R ¹⁵ or C=CR ¹² R ¹³ ; more preferably CR ¹⁴ R ¹⁵ .

In each case, two adjacent radicals Z ⁴ and Z ⁵ or Z ⁷ and Z ⁸ or Z ⁸ and Z ⁹ or Z ¹¹ and Z ¹² or Z ¹² and Z ¹³ or Z ¹³ and Z ¹⁴ may be combined Together, they represent groups selected from CR ¹⁰ =CR ¹¹ - and -C≡C-, where X-4 or X-5 may not contain more than one such group.

When X is X-2, it is preferred that one of Z ¹ and Z ² is a methylene group or a methylene halide, preferably a methylene group.

When X is X-3, it is preferred that at least two of Z ³ , Z ⁴ and Z ⁵ are substituted only by hydrogen or halogen, preferably hydrogen, or Z ⁴ together with Z ⁵ is -C≡C More preferably, two of Z ³ , Z ⁴ and Z ⁵ are independently methylene or halomethylene, preferably methylene. Preferably, Z ³ and Z ⁵ are a methylene group or a methylene halide, preferably a methylene group.

When X is X-4, it is preferred that at least three of Z ⁶ , Z ⁷ , Z ⁸ and Z ⁹ can be substituted only by hydrogen or halogen, preferably hydrogen, and the conditions are Z ⁷ and Z ⁸ Or Z ⁸ together with Z may be -C≡C-, more preferably at least three of Z ⁶ , Z ⁷ , Z ⁸ and Z ⁹ are independent methylene or halomethylene, preferably methylene base.

When X is X-5, it is preferred that at least four of Z ¹⁰ , Z ¹¹ , Z ¹² , Z ¹³ and Z ¹⁴ can be substituted only by hydrogen or halogen, preferably hydrogen, and the condition is Z ¹¹ Together with Z ¹² or Z ¹² and Z ¹³ or Z ¹³ and Z ¹⁴ may be -C≡C-, more preferably at least four of Z ¹⁰ , Z ¹¹ , Z ¹² , Z ¹³ and Z ¹⁴ are independent sub- Methyl or halogenated methylene, preferably methylene. Preferably, Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ are independently methylene or halomethylene, preferably methylene.

Wherein the radicals Z ¹ , Z ³ , Z ⁶ and Z ^{10 are} not substituted by OH; and Z ¹ , Z ² , Z ³ , Z ⁴ , Z ⁵ , Z ⁶ , Z ⁷ , Z ⁸ , Z ⁹ , Z ¹⁰ , Z ¹¹ , Z ¹² , Z ¹³ and Z ¹⁴ do not represent a carbon atom substituted by two OH groups.

Each individually independent R ¹⁰ and R ¹¹ represents hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or phenyl, wherein the phenyl is derived from one or more (eg One to five) groups independently selected from halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy The group is optionally substituted; or R ¹⁰ and R ¹¹ together with the carbon atom to which they are attached may form a C ₃ -C ₆ cycloalkyl group or a C ₃ -C ₆ halocycloalkyl group.

Preferably, each individually independent R ¹⁰ and R ¹¹ represents hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl.

More preferably, R ¹⁰ and R ¹¹ represent hydrogen.

Each individually independent R ¹² and R ¹³ represents hydrogen, halogen, C ₁ -C ₄ alkyl, or C ₁ -C ₄ haloalkyl.

Preferably, each individually independent R ¹² and R ¹³ represents hydrogen, halogen, methyl or halomethyl.

Each individually independent R ¹⁴ and R ¹⁵ represents hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or phenyl, wherein benzene The base is composed of one or more (for example one to five) from halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ halo a group independently selected by alkoxy groups is optionally substituted; or R ¹⁴ and R ¹⁵ together with the carbon atom to which they are attached may form a C ₃ -C ₆ cycloalkyl group or a C ₃ -C ₆ halo ring alkyl.

Preferably, each individually independent R ¹⁴ and R ¹⁵ represents hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or Phenyl, wherein the phenyl group is optionally substituted by one or more (e.g., one to five) groups independently selected from the group consisting of halogen, CN, methyl, halomethyl, methoxy, and halomethoxy.

Or R ¹⁴ and R ¹⁵ together with the carbon atom to which they are attached may form a C ₃ -C ₆ cycloalkyl group or a C ₃ -C ₆ halocycloalkyl group.

More preferably, R ¹⁴ and R ¹⁵ represent hydrogen.

Each individually independent R ¹⁶ and R ¹⁷ represents hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or phenyl, wherein the phenyl is derived from one or more (eg One to five) groups independently selected from halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy The group is selectively replaced.

Preferably, each individually independent R ¹⁶ and R ¹⁷ represents hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or phenyl, wherein the phenyl may be one Or multiple (e.g., one to five) groups independently selected from halogen, CN, methyl, halomethyl, methoxy, and halomethoxy groups for selective substitution.

The respective independently Y ¹ , Y ² and Y ³ represent hydrogen, halogen, CN, NO ₂ , C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl, phenyl, 5- or 6-membered heterocyclic ring (containing one to three heteroatoms independently selected from O, S and N, provided that the heterocyclic ring does not contain adjacent oxygen atoms, adjacent a sulfur atom, or an adjacent sulfur and oxygen atom (for example: a heterocyclic ring as defined herein, preferably a morpholinyl, pyrrolidinyl, piperidinyl, piperidine Or pyridyl, pyrrolyl, imidazolyl or triazolyl, for example: 1,2,4 triazolyl, more preferably morpholinyl, pyrrolidinyl, pyridyl or imidazolyl), COR ⁸ , OR ⁷ , SH, C ₁ -C ₈ alkylthio group, C ₁ -C ₈ alkylsulfinyl group, C ₁ -C ₈ alkylsulfonyl group, phenylthio group, phenyl sulfinylene group, Phenylsulfonyl, N(R ⁹ ) ₂ , CO ₂ R ⁷ , O(CO)R ⁸ , CON(R ⁹ ) ₂ , NR ⁹ COR ⁸ or CR ⁸ N-OR ⁷ , wherein alkyl, naphthenic The base, alkenyl, alkynyl, phenyl and heterocyclic ring may be one or more (for example one to five) from halogen, CN, NH ₂ , NO ₂ , OR ⁷ , C ₁ -C ₄ alkyl and C ₁ -C _a group independently selected by a _4- haloalkyl group for selective substitution; or Y ¹ and Y ³ , or Y ² and Y ³ together with a fragment of a pyridine ring to which it is attached may be partially or completely unsaturated. a 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, N and N(R ⁹ ), provided that The heterocycle does not contain adjacent oxygen atoms, adjacent sulfur atoms, or adjacent sulfur and oxygen atoms (eg, Y ¹ and Y ³ , Y ² and Y ³ together with The pyridyl ring fragment attached may be formed from isoquinoline; 5,6,7,8-tetrahydro-isoquinoline; 6,7-dihydro-5H-[2]azepine; 3,4 -dihydro-1H-pyrano[3,4-c]pyridine; 6,7,8,9-tetrahydro-5H-cyclohepta[c]pyridine and [1,7]naphthyridine Ring system)), and wherein the ring formed by Y ¹ and Y ³ , or Y ² and Y ³ may be from one or more (for example one to five) from halogen, CN, NH ₂ , NO ₂ , OH, C _A group independently selected from ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy is optionally substituted.

Preferably, each independently Y ¹ , Y ² and Y ³ represent hydrogen, halogen, CN, OR ⁷ , C ₁ -C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₃ -C ₈ cycloalkyl , phenyl, pyridyl, N(R ⁹ ) ₂ , CO ₂ R ⁷ , NR ⁹ COR ⁸ , SH, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfinylene, C ₁ -C ₈ alkylsulfonyl, phenylthio, phenylsulfinyl or phenylsulfonyl, wherein the alkyl, alkenyl, cycloalkyl, phenyl and pyridyl groups may be one or more (eg One to five) are selectively substituted from a group independently selected from halogen, CN, OR ⁷ , C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl.

More preferably, each independently Y ¹ , Y ² and Y ³ represent hydrogen, halogen, OR ⁷ , CN, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, N(R ⁹ ) ₂ , phenyl, CO ₂ R ⁷ or NR ⁹ COR ⁸ , wherein the alkyl group, the cycloalkyl group and the phenyl group may be one or more (for example one to five) from halogen, CN, C ₁ -C ₄ alkyl, C ₁ An independently selected group of -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy is optionally substituted.

More preferably, each independently Y ¹ , Y ² and Y ³ represent hydrogen, halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₆ olefin a C ₃ -C ₆ cycloalkyl group, N(R ⁹ ) ₂ , phenyl or CO ₂ R ⁷ wherein the alkyl group, the alkoxy group, the alkenyloxy group, the cycloalkyl group and the phenyl group may be one or more ( For example, one to five) independently selected from halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy The group is optionally substituted.

More preferably, each of the independent Y ¹ , Y ² and Y ³ represents hydrogen, halogen, C ₁ -C ₄ alkyl, CN or C ₁ -C ₄ alkoxy, wherein the alkyl group and the alkoxy group may be one Or a plurality (for example, one to five) of groups independently selected from halogen, CN, C ₁ -C ₄ alkyl and C ₁ -C ₄ haloalkoxy are optionally substituted.

More preferably, each independently Y ¹ , Y ² and Y ³ represent hydrogen, C ₁ -C ₄ alkyl or C ₂ -C ₄ alkenyl, wherein the alkyl and alkenyl groups may be one or more (eg one to Five) are selectively substituted from groups independently selected from halogen, CN, methoxy and halomethoxy.

More preferably, each independently Y ¹ , Y ² and Y ³ represent hydrogen or a C ₁ -C ₄ alkyl group.

In a group of compounds, each independently Y ¹ and Y ² represents hydrogen, halogen, C ₁ -C ₄ alkyl, CN or C ₁ -C ₄ alkoxy, wherein the alkyl and alkoxy groups may be more than one (eg One to five) groups independently selected from halogen, CN, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy, and Y ³ is defined according to any of the above Item definition.

A ¹ represents ring A-1, A-2, A-3, A-4, A-5, A-6 or A-7:

Preferably, A ¹ represents ring A-1, A-2 or A-4.

More preferably, A ¹ represents ring A-1 or A-2.

More preferably, A ¹ represents ring A-1.

Each independently R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ and R ²² represent hydrogen, halogen, CN, NO ₂ , C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₂ -C ₈ olefin a C ₂ -C ₈ alkynyl group, a phenyl group, a 5- or 6-membered heterocyclic ring (containing one to three heteroatoms independently selected from O, S and N, provided that the heterocyclic ring does not contain adjacent An oxygen atom, an adjacent sulfur atom, or an adjacent sulfur and oxygen atom (for example, a heterocyclic ring as defined herein, preferably a morpholinyl group, a pyrrolidinyl group, a piperidinyl group, a piperidine group) a pyridyl group, a pyrrolyl group, an imidazolyl group, a triazolyl group, for example, a 1,2,4 triazolyl group, more preferably a morpholinyl group, a pyrrolidinyl group, a pyridyl group or an imidazolyl group), a benzyl group, COR ⁸ , OR ⁷ , SH, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfinylene, C ₁ -C ₈ alkylsulfonyl, phenylthio, phenylsulfin Anthracenyl, phenylsulfonyl, N(R ⁹ ) ₂ , CO ₂ R ⁷ , O(CO)R ⁸ , CON(R ⁹ ) ₂ , NR ⁹ COR ⁸ or CR ⁸ N-OR ⁷ , wherein alkyl , cycloalkyl, alkenyl, alkynyl, phenyl, heterocyclic and benzyl may be derived from one or more (eg one to five) from halogen, CN, NH ₂ , NO ₂ , OR ⁷ , C ₁ -C ₄ alkane a group independently selected by a C ₁ -C ₄ haloalkyl group; or R ¹⁸ and R ²¹ , R ¹⁸ and R ²² or R ²⁰ and R ²¹ together with the ring to which it is attached Fragments, which may form partially or fully unsaturated 5- to 7-membered carbocyclic rings, or partially or fully unsaturated 5- to 7-membered heterocyclic rings (containing one to three from O, S, N and N (R) ⁹ ) independently selected heteroatoms, provided that the heterocycle does not contain adjacent oxygen atoms, adjacent sulfur atoms, or adjacent sulfur and oxygen atoms (eg, R ¹⁸ And R ²¹ , R ¹⁸ and R ²² , or R ²⁰ and R ²¹ together with the ring segment attached thereto, may be formed by isoquinoline; 5,6,7,8-tetrahydro-isoquinoline; ,7-dihydro-5H-[2]azepine; 3,4-dihydro-1H-pyrano[3,4-c]pyridine; 6,7,8,9-tetrahydro-5H-cycloheptane Alkano[c]pyridine; [1,7]naphthyridine; quinoline; 5,6,7,8-tetrahydro-quinoline; 6,7-dihydro-5H-[1]azepine, [1, 8] naphthyridine; 6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine; selected from 7,8-dihydro-5H-pyrano[4,3-b]pyridine Ring system)), and wherein the ring formed by R ¹⁸ and R ²¹ , R ¹⁸ and R ²² or R ²⁰ and R ²¹ may be from one or more (for example one to five) from halogen, CN, NH ₂ , Selectable groups independently selected from NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy Replacement.

Preferably, each independently R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ and R ²² represent hydrogen, halogen, CN, OR ⁷ , C ₁ -C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₃ -C ₈ cycloalkyl, phenyl, pyridyl, benzyl, N(R ⁹ ) ₂ , CO ₂ R ⁷ , NR ⁹ COR ⁸ , CR ⁸ N-OR ⁷ , SH, C ₁ -C ₈ alkyl sulfur Alkyl, C ₁ -C ₈ alkylsulfinyl, C ₁ -C ₈ alkylsulfonyl, phenylthio, phenylsulfinyl or phenylsulfonyl, wherein alkyl, alkenyl, The cycloalkyl, phenyl, pyridyl and benzyl groups can be independently selected from one or more (for example one to five) from halogen, CN, OR ⁷ , C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl. The group is selectively substituted.

More preferably, each independently R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ and R ²² represent hydrogen, halogen, OR ⁷ , CN, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, N(R ⁹ ) ₂ , C ₁ -C ₄ alkylthio group, C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ alkylsulfonyl group, phenyl group, benzyl group, CO ₂ R ⁷ , CR ⁸ N-OR ⁷ or NR ⁹ COR ⁸ , wherein the alkyl group, the cycloalkyl group, the phenyl group and the benzyl group may be one or more (for example one to five) from halogen, CN, C ₁ -C ₄ alkyl A group independently selected from C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, or C ₁ -C ₄ haloalkoxy is optionally substituted.

More preferably, R ¹⁸ represents hydrogen, halogen, C ₁ -C ₄ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ alkynyloxy, CN, C ₁ -C ₄ alkane a group, NH ₂ , N(C ₁ -C ₄ alkyl) ₂ , C ₁ -C ₄ alkylthio, phenyl, benzyl, phenoxy or benzyloxy, wherein alkyl, alkoxy, Alkenyloxy, alkynyloxy, phenoxy, benzyloxy, phenyl and benzyl may be one or more (for example one to five) from halogen, CN, methyl, halomethyl, methoxy and halo The groups independently selected from the oxy group are optionally substituted.

More preferably, R ¹⁹ represents hydrogen, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl.

More preferably, R ¹⁹ represents hydrogen or C ₁ -C ₄ alkyl.

More preferably, R ²⁰ represents hydrogen, halogen, OH, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, NH ₂ , C ₁ -C ₄ alkylthio, phenyl Or a benzyl group, wherein the alkyl group, the cycloalkyl group, the phenyl group and the benzyl group are independently of one or more (for example one to five) from halogen, CN, methyl, halomethyl, methoxy and halomethoxy. The selected groups are selectively substituted.

More preferably, R ²⁰ represents hydrogen, halogen, OH, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, NH ₂ , C ₁ -C ₄ alkylthio, phenyl Or a benzyl group, wherein the alkyl group, the cycloalkyl group, the phenyl group and the benzyl group are independently of one or more (for example one to five) from halogen, CN, methyl, halomethyl, methoxy and halomethoxy. The selected groups are selectively substituted.

More preferably, R ²¹ represents hydrogen, halogen, OH, C ₁ -C ₄ alkyl, CO ₂ H, CO ₂ (C ₁ -C ₄ alkyl), C (C ₁ -C ₄ alkyl) NO (C ₁ -C ₄ alkyl) or CHN-OH, wherein the alkyl group, the cycloalkyl group, the phenyl group and the benzyl group may be one or more (for example one to five) from halogen, CN, C ₁ -C ₄ The alkyl group, the C ₁ -C ₄ haloalkyl group, the C ₁ -C ₄ alkoxy group and the C ₁ -C ₄ haloalkoxy group are independently selected to be selectively substituted.

More preferably, R ²² represents hydrogen, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl.

More preferably, R ²² represents hydrogen or a C ₁ -C ₄ alkyl group.

In a group of compounds, independently R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ and R ²² represent hydrogen, halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C _3- C ₆ alkenyloxy, C ₃ -C ₆ cycloalkyl, N(R ⁹ ) ₂ , C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ - C ₄ alkylsulfonyl, phenyl, phenoxy, benzyl, CR ⁸ N-OR ⁷ or CO ₂ R ⁷ wherein alkyl, alkoxy, alkenyloxy, cycloalkyl, phenyl and benzyl The group may be one or more (for example one to five) from halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkyl The groups independently selected from the oxy group are optionally substituted.

More preferably, in this group of compounds, independently R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ and R ²² represent hydrogen, C ₁ -C ₄ alkyl, CN or C ₁ -C ₄ alkoxy, Wherein the alkyl group and the alkoxy group are selected from one or more (for example one to five) groups independently selected from halogen, CN, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy. Sexual substitution.

Each of the respective independent R ⁷ represents hydrogen, C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl, C ₁ -C ₄ alkyl a sulfonyl group, a phenyl group, a benzyl group or a 5- or 6-membered heterocyclic ring (containing one to three heteroatoms independently selected from O, S and N, provided that the heterocyclic ring does not contain an adjacent oxygen atom, An adjacent sulfur atom, or an adjacent sulfur and oxygen atom), wherein the alkyl group, the cycloalkyl group, the alkenyl group, the alkynyl group, the phenyl group, the benzyl group and the heterocyclic ring are one or more (for example, one to five) From halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C _a group independently selected from ₁ -C ₄ -alkyl-C ₁ -C ₄ -alkoxy and C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl; The ring is preferably as defined herein, especially morpholinyl, pyrrolidinyl, piperidinyl, piperidine A pyridyl group, a pyrrolyl group, an imidazolyl group or a triazolyl group, for example, a 1,2,4triazolyl group, more preferably a morpholinyl group, a pyrrolidinyl group, a pyridyl group or an imidazolyl group.

Preferably, each independently R ⁷ represents hydrogen, C ₁ -C ₈ alkyl, C ₁ -C ₈ haloalkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl, C _3- C ₈ haloalkenyl, C ₃ -C ₈ haloalkynyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, phenyl, benzyl or pyridyl, wherein Phenyl, benzyl and pyridyl are from one or more (for example one to five) from halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, The C ₁ -C ₄ alkoxy group and the C ₁ -C ₄ haloalkoxy group are independently selected to be selectively substituted.

More preferably, each independently R ⁷ represents hydrogen, C ₁ -C ₈ alkyl, C ₁ -C ₈ haloalkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl, C _3- C ₈ haloalkenyl, C ₃ -C ₈ haloalkynyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, phenyl, benzyl or pyridyl, wherein Phenyl, benzyl and pyridyl are from one or more (for example one to five) from halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy The group independently selected from the C ₁ -C ₄ haloalkoxy group is selectively substituted.

More preferably, each independently R ⁷ represents hydrogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl.

Each individually independent R ⁸ represents hydrogen, C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl, phenyl, benzyl or pyridine a group wherein alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl, pyridyl is derived from one or more (eg, one to five) from halogen, CN, NH ₂ , NO ₂ , OH, C _a group selected independently of ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy is optionally substituted; preferably Then, each independently R ⁸ represents hydrogen, C ₁ -C ₈ alkyl or C ₁ -C ₈ haloalkyl.

More preferably, each independently R ⁸ represents hydrogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl.

Each of the respective independent R ⁹ represents hydrogen, OH, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl or COR ⁸ wherein alkyl, alkoxy, alkenyl, alkynyl may be optionally substituted by more than one halogen; wherein when two R ⁹ groups are attached the same In the case of a nitrogen atom, these groups may be the same or different; wherein when two R ⁹ groups are attached to the same nitrogen atom, neither of the two groups may be OH, C ₁ -C ₄ alkoxy or C _{a 1-} C ₄ haloalkoxy group, wherein when two R ⁹ groups are attached to the same nitrogen atom, the two groups together with the nitrogen atom to which they are attached may form a ring B-1, B-2, B-3, B-4, B-5, B-6, B-7 or B-8:

The ring formed therein is derived from halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C One or more (e.g., one to five) groups independently selected from the ₄ -haloalkoxy group are selectively substituted.

Preferably, each independently R ⁹ represents hydrogen, C ₁ -C ₈ alkyl or COR ⁸ ; wherein when the two R ⁹ groups are attached to the same nitrogen atom, the groups may be the same or different Wherein, when two R ⁹ groups are attached to the same nitrogen atom, the two groups, together with the nitrogen atom to which they are attached, may form rings B-1, B-2, B-3, B-4. Or B-5, wherein the ring formed may be optionally substituted by one or more (e.g., one to five) groups independently selected from the group consisting of halogen, methyl, and halomethyl.

More preferably, each independently R ⁹ represents hydrogen or a C ₁ -C ₄ alkyl group; wherein when the two R ⁹ groups are attached to the same nitrogen atom, the groups may be the same or different; Wherein when two R ⁹ groups are attached to the same nitrogen atom, the two groups, together with the nitrogen atom to which they are attached, may form a ring B-1, B-2, B-3, B-4 or B- 5. The ring formed therein may be selectively substituted by one or more (e.g., one to five) groups independently selected from a halogen, a methyl group, and a halomethyl group.

In a preferred group of compounds: R ¹ represents hydrogen, C ₁ -C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl, C ₃ -C ₈ cycloalkyl, phenyl, Pyridyl or (R ⁷ O)carbonyl (C ₁ -C ₄ alkyl) wherein the alkyl, cycloalkyl, phenyl and pyridyl groups may be derived from one or more of halogen, CN, OR ⁷ , NH ₂ , NH- C ₁ -C ₈ alkyl, N(C ₁ -C ₈ alkyl) ₂ , C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ cycloalkyl are independently of pyridyl Selected groups are optionally substituted; D ¹ represents N or CY ¹ ; D ² represents CY ² ; D ³ represents N or CR ⁶ ; D ⁴ represents CR ⁵ ; each independently R ² , R ⁴ , R ⁵ and R ⁶ represents hydrogen, halogen, CN, OR ⁷ , C ₁ -C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₃ -C ₈ cycloalkyl, phenyl, pyridyl, N(R ⁹ ) ₂ , CO ₂ R ⁷ , NR ⁹ COR ⁸ , SH, C ₁ -C ₈ alkylthio group, C ₁ -C ₈ alkylsulfinyl group, C ₁ -C ₈ alkylsulfonyl group, phenylthio group, Phenylsulfinyl or phenylsulfonyl, wherein the alkyl, alkenyl, cycloalkyl, phenyl and pyridyl groups may be derived from one or more of halogen, CN, OR ⁷ , C ₁ -C ₄ alkyl, Selectively selected groups of C ₁ -C ₄ haloalkyl groups for selective extraction Or R ⁴ and R ⁵ , R ⁵ and R ² , or R ² and R ⁶ together with the pyridine ring segment attached thereto, may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring, or Is a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, N and N(R ⁹ ), provided that the heterocyclic ring does not contain adjacent oxygen An atom, an adjacent sulfur atom, or an adjacent sulfur and oxygen atom), and wherein the ring formed by R ⁴ and R ⁵ , R ⁵ and R ² or R ² and R ⁶ may be one or more halogen a group independently selected from CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy X represents X-3 or X-5; each independently Z ³ , Z ⁵ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ represents CR ¹⁰ R ¹¹ or C=CR ¹² R ¹³ ; Z ⁴ and Z ¹² represent CR ¹⁴ R ¹⁵ or C=CR ¹² R ¹³ ; or in each case, two adjacent radicals Z ⁴ and Z ⁵ or Z ¹¹ and Z ¹² or Z ¹² and Z ¹³ or Z ¹³ and Z ¹⁴ , possibly Taken together to represent a group selected from -CR ¹⁰ =CR ¹¹ - and -C≡C-, wherein X-3 or X-5 may not contain more than one such group; each one Further independent R ¹⁰ and R ¹¹ represent hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl; each individually independent R ¹² and R ¹³ represent hydrogen, halogen, C _1- C ₄ alkyl, C ₁ -C ₄ haloalkyl; each individually independent R ¹⁴ and R ¹⁵ represents hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ halo a C ₁ -C ₄ alkoxy group or a phenyl group, wherein the phenyl group may be independently selected from one or more of halogen, CN, methyl, halomethyl, methoxy and halomethoxy. To replace it selectively.

Or R ¹⁴ and R ¹⁵ together with the carbon atom to which they are attached may form a C ₃ -C ₆ cycloalkyl group or a C ₃ -C ₆ halocycloalkyl group; each independently Y ¹ , Y ² and Y ³ represent hydrogen , halogen, CN, OR ⁷ , C ₁ -C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₃ -C ₈ cycloalkyl, phenyl, pyridyl, N(R ⁹ ) ₂ , CO ₂ R ⁷ , NR ⁹ COR ⁸ , SH, C ₁ -C ₈ alkylthio group, C ₁ -C ₈ alkylsulfinyl group, C ₁ -C ₈ alkylsulfonyl group, phenylthio group, phenylsulfinylene Mercapto or phenylsulfonyl, wherein alkyl, alkenyl, cycloalkyl, phenyl and pyridyl may be derived from one or more of halogen, CN, OR ⁷ , C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl groups independently selected for selective substitution; A ¹ represents ring A-1, A-2, A-3, A-4, A-5, A-6 or A-7; R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ and R ²² represent hydrogen, halogen, CN, OR ⁷ , C ₁ -C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₃ -C ₈ cycloalkyl, benzene Base, pyridyl, benzyl, N(R ⁹ ) ₂ , CO ₂ R ⁷ , NR ⁹ COR ⁸ , CR ⁸ N-OR ⁷ , SH, C ₁ -C ₈ alkylthio group, C ₁ -C ₈ alkylsulfinyl acyl, C ₁ -C ₈ alkylsulfonyl, phenylthio, phenylsulfinyl or acyl benzene Sulfo acyl, wherein the alkyl, alkenyl, cycloalkyl, phenyl, pyridyl and benzyl groups may be one or more selected from _{^{halogen, CN, OR 7, C 1}} -C 4 alkyl, C ₁ -C ₄ halogen The independently selected groups of alkyl groups are optionally substituted; each independently R ⁷ represents hydrogen, C ₁ -C ₈ alkyl, C ₁ -C ₈ haloalkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ haloalkenyl, C ₃ -C ₈ haloalkynyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, phenyl, benzyl or pyridyl, wherein benzene a group, a benzyl group and a pyridyl group are one or more selected from the group consisting of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy a group optionally substituted with a C ₁ -C ₄ haloalkoxy group; each independently R ⁸ represents hydrogen, C ₁ -C ₈ alkyl or C ₁ -C ₈ haloalkyl .

Each of the respective independent R ⁹ represents hydrogen, C ₁ -C ₈ alkyl or COR ⁸ ; wherein when two R ⁹ groups are attached to the same nitrogen atom, these groups may be the same or different; When the R ⁹ groups are attached to the same nitrogen atom, the two groups together with the nitrogen atom to which they are attached may form a ring B-1, B-2, B-3, B-4 or B-5, wherein The ring formed can be selectively substituted by one or more groups independently selected from the group consisting of halogen, methyl and halomethyl.

In a preferred group of compounds: R ¹ represents hydrogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, phenyl or pyridyl, wherein the alkyl, alkenyl, phenyl and pyridyl groups may be Or a plurality of halogens, CN, OH, NH ₂ , NH-C ₁ -C ₄ alkyl, N(C ₁ -C ₄ alkyl) ₂ , C ₁ -C ₄ alkyl, C ₁ -C ₄ halo The group independently selected from the group consisting of a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ haloalkoxy group and a C ₃ -C ₆ cycloalkyl group is optionally substituted.

D ¹ represents N or CY ¹ ; D ² represents CY ² ; D ³ represents N or CR ⁶ ; D ⁴ represents CR ⁵ ; each independently R ² , R ⁴ , R ⁵ and R ⁶ represent hydrogen, halogen, OR ⁷ , CN, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, N(R ⁹ ) ₂ , phenyl, CO ₂ R ⁷ or NR ⁹ COR ⁸ wherein alkyl, cycloalkyl and phenyl may be One or more groups independently selected from halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy Selective substitution; or R ⁴ and R ⁵ , R ⁵ and R ² , or R ² and R ⁶ together with the pyridyl ring segment to which they are attached may form a fully or partially unsaturated 5- or 6 a metacarbocyclic ring and may be optionally substituted by one or more groups independently selected from halogen, methyl and halomethyl; X represents X-3; each independently Z ³ and Z ⁵ represents CR ¹⁰ R ¹¹ or C=CR ¹² R ¹³ ; Z ⁴ represents CR ¹⁴ R ¹⁵ or C=CR ¹² R ¹³ ; or Z ⁴ together with Z ⁵ represents selected from -CR ¹⁰ =CR ¹¹ - and -C≡C- a group; each individually independent R ¹⁰ and R ¹¹ represents hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl; each individually independent R ¹² and R ¹³ represent hydrogen, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl; each individually independent R ¹⁴ and R ¹⁵ represent hydrogen, halogen, CN, OH, C ₁ -C _{a 4} alkyl group, a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₄ alkoxy group or a phenyl group, wherein the phenyl group may be derived from one or more of halogen, CN, methyl, halomethyl, methoxy and The groups independently selected from the halomethoxy group are optionally substituted.

Or R ¹⁴ and R ¹⁵ together with the carbon atom to which they are attached may form a C ₃ -C ₆ cycloalkyl group or a C ₃ -C ₆ halocycloalkyl group; wherein at least two of Z ³ , Z ⁴ and Z ⁵ Can only be replaced by hydrogen, or Z ⁴ and Z ⁵ together represent -C≡C-; each independently Y ¹ , Y ² and Y ³ represent hydrogen, halogen, OR ⁷ , CN, C ₁ -C ₄ alkyl a C ₃ -C ₆ cycloalkyl group, N(R ⁹ ) ₂ , phenyl, CO ₂ R ⁷ or NR ⁹ COR ⁸ , wherein the alkyl group, the cycloalkyl group and the phenyl group may be one or more selected from the group consisting of halogen, CN, a group independently selected from C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy; A ¹ represents a ring A-1, A-2 or A-4; each independently R ¹⁸ , R ²⁰ , R ²¹ and R ²² represent hydrogen, halogen, OR ⁷ , CN, C ₁ -C ₄ alkyl, C ₃ -C ₆ ring Alkyl, N(R ⁹ ) ₂ , C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinylene, C ₁ -C ₄ alkylsulfonyl, phenyl, benzyl, CO ₂ R ⁷ , CR ⁸ N-OR ⁷ or NR ⁹ COR ⁸ , wherein the alkyl group, the cycloalkyl group, the phenyl group and the benzyl group may be one or more from halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy Individually selected groups are optionally substituted; each independently R ⁷ represents hydrogen, C ₁ -C ₈ alkyl, C ₁ -C ₈ haloalkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ -haloalkenyl, C ₃ -C ₈ alkynyl, C ₃ -C ₈ haloalkynyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, phenyl, benzyl Or pyridyl, wherein phenyl, benzyl and pyridyl are derived from one or more of halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy The groups independently selected by the C ₁ -C ₄ haloalkoxy group are optionally substituted; each independently R ⁸ represents hydrogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl.

Each of the respective independent R ⁹ represents hydrogen or C ₁ -C ₄ alkyl; wherein when two R ⁹ groups are attached to the same nitrogen atom, these groups may be the same or different; wherein when two R ⁹ When the same nitrogen atom is attached, the two groups together with the nitrogen atom to which they are attached may form a ring B-1, B-2, B-3, B-4 or B-5, wherein The ring may be optionally substituted by one or more groups independently selected from the group consisting of halogen, methyl and halomethyl.

In a preferred group of compounds: R ¹ represents hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, phenyl or pyridin-2-yl, wherein phenyl and pyridyl-2- The group may be optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy; D ¹ represents CY ¹ ; D ² represents CY ² ; D ³ represents CR ⁶ ; D ⁴ represents CR ⁵ ; each independently R ² , R ⁴ , R ⁵ and R ⁶ represent hydrogen, halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy , C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ cycloalkyl, N(R ⁹ ) ₂ , phenyl or CO ₂ R ⁷ , wherein alkyl, alkoxy, alkenyloxy, cycloalkyl And the phenyl group may be independently selected from one or more of halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy The selected group is optionally substituted; or R ⁴ and R ⁵ , R ⁵ and R ² , or R ² and R ⁶ together with the pyridyl ring segment to which they are attached may form complete or partial unsaturation a 6-membered carbocyclic ring and may be optionally substituted by one or more groups independently selected from the group consisting of halogen, methyl and halomethyl; X Table X-3; each independently Z ³ and Z ⁵ Representative CR ¹⁰ R ¹¹ or ^{C = CR 12 R 13; Z} 4 Representative CR ¹⁴ R ¹⁵ or C = CR ¹² R ^13; or Z ⁴ representatives from together with Z ⁵ -CR ¹⁰ =CR ¹¹ - and -C≡C- selected groups; each individually independent R ¹⁰ and R ¹¹ represents hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl or C ₁ - C ₄ haloalkyl; each individually independent R ¹² and R ¹³ represents hydrogen, halogen, methyl or halomethyl.

Each individually independent R ¹⁴ and R ¹⁵ represents hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or phenyl, wherein benzene The group may be optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy.

Or R ¹⁴ and R ¹⁵ together with the carbon atom to which they are attached may form a C ₃ -C ₆ cycloalkyl group or a C ₃ -C ₆ halocycloalkyl group; wherein at least two of Z ³ , Z ⁴ and Z ⁵ One can only be substituted by hydrogen, or Z ⁴ and Z ₅ together represent -C≡C-; each independently Y ¹ , Y ² and Y ³ represent hydrogen, halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ cycloalkyl, N(R ⁹ ) ₂ , phenyl or CO ₂ R ⁷ wherein alkyl, alkoxy, Alkenyloxy, cycloalkyl and phenyl may be one or more from halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C _a group independently selected by a ₄ -haloalkoxy group for selective substitution; A ¹ represents a ring A-1, A-2 or A-4; and each independently R ¹⁸ , R ²⁰ , R ²¹ and R ²² represent hydrogen, Halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ cycloalkyl, N(R ⁹ ) ₂ , C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, phenyl, phenoxy, benzyl, benzyloxy, CR ⁸ N- oR ⁷ or CO ₂ R ^7, wherein the alkyl, alkoxy, alkenyloxy, cycloalkyl, phenyl Benzyl by one or more selected from halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy are independently selected from The resulting group is optionally substituted; each independently R ⁷ represents hydrogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl; each independently R ⁹ represents hydrogen or C ₁ -C _{a 4-} alkyl group; wherein when two R ⁹ groups are attached to the same nitrogen atom, these groups may be the same or different; wherein when two R ⁹ groups are attached to the same nitrogen atom, the two groups together The nitrogen atom to which it is attached may form a ring B-1, B-2, B-3, B-4 or B-5, wherein the ring formed may be one or more from halogen, methyl and halo The independently selected groups are selectively substituted.

In a preferred group of compounds: R ¹ represents hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, phenyl or pyridin-2-yl, wherein phenyl and pyridyl-2- The group may be optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy; D ¹ represents CY ¹ ; D ² represents CY ² ; D ³ represents CR ⁶ ; D ⁴ represents CR ⁵ ; each independently R ² , R ⁴ , R ⁵ and R ⁶ represent hydrogen, halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy , C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ cycloalkyl, N(R ⁹ ) ₂ , phenyl or CO ₂ R ⁷ , wherein alkyl, alkoxy, alkenyloxy, cycloalkyl And the phenyl group may be independently selected from one or more of halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy The selected group is optionally substituted; or R ⁴ and R ⁵ , R ⁵ and R ² , or R ² and R ⁶ together with the pyridyl ring segment to which they are attached may form complete or partial unsaturation a 6-membered carbocyclic ring and may be optionally substituted by one or more groups independently selected from the group consisting of halogen, methyl and halomethyl; X Table X-3; each independently Z ³ and Z ⁵ Representative CR ¹⁰ R ¹¹ or ^{C = CR 12 R 13; Z} 4 Representative CR ¹⁴ R ¹⁵ or C = CR ¹² R ^13; or Z ⁴ representatives from together with Z ⁵ -CR ¹⁰ =CR ¹¹ - and -C≡C- selected groups; each individually independent R ¹⁰ and R ¹¹ represents hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl or C ₁ - C ₄ haloalkyl; each individually independent R ¹² and R ¹³ represents hydrogen, halogen, methyl or halomethyl.

Each individually independent R ¹⁴ and R ¹⁵ represents hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or phenyl, wherein benzene The group may be optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy.

Or R ¹⁴ and R ¹⁵ together with the carbon atom to which they are attached may form a C ₃ -C ₆ cycloalkyl group or a C ₃ -C ₆ halocycloalkyl group; wherein at least two of Z ³ , Z ⁴ and Z ⁵ One can only be substituted by hydrogen, or Z ⁴ and Z ⁵ together represent -C≡C-; each independently Y ¹ , Y ² and Y ³ represent hydrogen, halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ cycloalkyl, N(R ⁹ ) ₂ , phenyl or CO ₂ R ⁷ wherein alkyl, alkoxy, Alkenyloxy, cycloalkyl and phenyl may be one or more from halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C _a group independently selected by a ₄ -haloalkoxy group for selective substitution; A ¹ represents a ring A-1, A-2 or A-4; and each independently R ¹⁸ , R ²⁰ , R ²¹ and R ²² represent hydrogen, Halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ cycloalkyl, N(R ⁹ ) ₂ , C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, phenyl, phenoxy, benzyl or CO ₂ R ⁷ , wherein alkyl , alkoxy, alkenyloxy, cycloalkyl, phenyl and benzyl may be one or more Selected from halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy groups are independently selected out of the group selectively Substituted; each independently R ⁷ represents hydrogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl; each independently R ⁹ represents hydrogen or C ₁ -C ₄ alkyl; When the R ⁹ groups are attached to the same nitrogen atom, these groups may be the same or different; wherein when the two R ⁹ groups are attached to the same nitrogen atom, the two groups together with the nitrogen atom to which they are attached , may form a ring B-1, B-2, B-3, B-4 or B-5, wherein the ring formed may be independently selected from one or more groups selected from the group consisting of halogen, methyl and halomethyl. The group is selectively replaced.

In one group of compounds, R ¹ represents pyridyl, and may be derived from one or more of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ - Selectively substituted with a C ₄ alkoxy group, a C ₁ -C ₄ haloalkoxy group, a C ₃ -C ₆ cycloalkyl group and a 5- or 6-membered heterocyclic ring containing one to three The heteroatoms independently selected from O, S and N, provided that the heterocycle does not contain adjacent oxygen atoms, adjacent sulfur atoms, or adjacent sulfur and oxygen atoms. The heterocyclic ring is preferably as defined herein, preferably morpholinyl, pyrrolidinyl, piperidinyl, piperidine A pyridyl group, a pyrrolyl group, an imidazolyl group or a triazolyl group, for example, a 1,2,4triazolyl group, more preferably a morpholinyl group, a pyrrolidinyl group, a pyridyl group or an imidazolyl group.

In another group of compounds, A ² and R ¹ represent pyridin-2-yl, which may be derived from one or more of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ a group selected by a haloalkyl group, a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ haloalkoxy group, a C ₃ -C ₆ cycloalkyl group and a 5- or 6-membered heterocyclic ring, The heterocyclic ring contains one to three heteroatoms independently selected from O, S and N, provided that the heterocyclic ring does not contain adjacent oxygen atoms, adjacent sulfur atoms, or adjacent sulfur and oxygen atoms. Heterocycles are preferably as defined herein, especially morpholinyl, pyrrolidinyl, piperidinyl, piperidine A pyridyl group, a pyrrolyl group, an imidazolyl group or a triazolyl group, for example, a 1,2,4triazolyl group, more preferably a morpholinyl group, a pyrrolidinyl group, a pyridyl group or an imidazolyl group.

In another group of compounds, A ² and R ¹ represent the same substituents.

In another group of compounds, R ¹ represents C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, phenyl or pyridyl, wherein alkyl, alkenyl, phenyl and pyridyl may be derived from more than one halogen. The CN, C ₁ -C ₄ alkoxy group and the C ₁ -C ₄ haloalkoxy group are independently selected to be selectively substituted.

In another group of compounds: X represents X-3; Z ³ and Z ⁵ represent methylene; Z ⁴ represents CR ¹⁴ R ¹⁵ or C=CR ¹² R ¹³ ; each individually independent R ¹² and R ¹³ represent hydrogen , halogen, methyl or halomethyl.

Each individually independent R ¹⁴ and R ¹⁵ represents hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or phenyl, wherein benzene The group may be optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy.

Or R ¹⁴ and R ¹⁵ together with the carbon atom to which they are attached may form a C ₃ -C ₆ cycloalkyl group which is optionally substituted by a halogen.

In another group of compounds, when A ¹ is A-1 and D ¹ is CY ¹ , then R ²² and Y ¹ together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbon. a ring, or a partially or fully unsaturated 5- to 7-membered heterocyclic ring (containing one to three heteroatoms independently selected from O, S, N and N(R ⁹ ), provided that the heterocyclic ring does not comprise a phase a neighboring oxygen atom, an adjacent sulfur atom, or an adjacent sulfur and oxygen atom), and wherein the ring formed by R ²² and Y ¹ may be derived from one or more of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy are independently of C ₁ -C ₄ alkylthio group The selected groups are selectively substituted.

Among the compounds of this group, R ²² and Y ¹ together with the fragment to which they are attached may preferably form a partially or fully unsaturated 6-membered carbocyclic ring or a partially or fully unsaturated 6-membered heterocyclic ring. a ring containing one to three heteroatoms independently selected from O, S, N and N(R ⁹ ), provided that the heterocycle does not contain adjacent oxygen atoms, adjacent sulfur atoms, or adjacent sulfur And an oxygen atom), and wherein the ring formed by R ²² and Y ¹ may be one or more halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ halogen A group independently selected from an alkyl group, a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ haloalkoxy group and a C ₁ -C ₄ alkylthio group is optionally substituted.

Among the compounds of this group, more preferably R ²² and Y ¹ together with the fragment to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring or a partially or fully unsaturated 6-membered heterocyclic ring. a ring containing a hetero atom independently selected from O, S, N and N(R ⁹ ), and wherein the ring formed by R ²² and Y ¹ may be one or more from halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ alkylthio Individually selected groups are selectively substituted.

Among the compounds of this group, R ²² and Y ¹ together with the fragment to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring or a partially or fully unsaturated 6-membered heterocyclic ring. a ring containing a hetero atom independently selected from N, and wherein the ring formed by R ²² and Y ¹ may be one or more halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl a group independently selected from a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ haloalkoxy group, and a C ₁ -C ₄ alkylthio group, optionally Replace.

Among the compounds of this group, still more preferably R ²² and Y ¹ together with the fragment to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring, wherein R ²² and Y ¹ are formed. Ring, which may be derived from one or more of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C _The group independently selected from the ₄ -haloalkoxy group and the C ₁ -C ₄ alkylthio group is selectively substituted.

Among the compounds of this group, even more preferably R ²² and Y ¹ together with the fragment to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring, wherein R ²² and Y ¹ are formed. The ring may be optionally substituted by one or more groups independently selected from the group consisting of halogen, CN, NH ₂ , NO ₂ , OH, methyl, halomethyl, methoxy and methylthio.

Further among this group of compounds, R ²² and Y ¹ together with the fragment to which they are attached may form a fully unsaturated 6-membered carbocyclic ring in which a ring formed by R ²² and Y ¹ is formed. It may be optionally substituted by one or more groups independently selected from halogen, CN, NH ₂ , NO ₂ , OH, methyl, halomethyl, methoxy and methylthio.

In one group of compounds, R ¹ represents C ₁ -C ₄ alkyl; D ¹ is CY ¹ ; D ² is CY ² ; D ³ is CY ³ ; D ⁴ is CY ⁴ ; each independently R ² , R ⁴ , R ⁵ and R ⁶ represent hydrogen, C ₁ -C ₄ alkyl or C ₂ -C ₄ alkenyl, wherein alkyl and alkenyl may be derived from one or more (eg one to five) from halogen, CN, methoxy and The groups independently selected from the halomethoxy group are optionally substituted; X represents X-3; Z ³ and Z ⁵ represent CR ¹⁰ R ¹¹ ; Z ⁴ represents CR ¹⁴ R ¹⁵ ; R ¹⁰ , R ¹¹ , R ¹⁴ and R ¹⁵ represents hydrogen; each independently Y ¹ , Y ² and Y ³ represent hydrogen or C ₁ -C ₄ alkyl; A ¹ represents ring A-1 or A-2; R ¹⁸ represents hydrogen, halogen, C ₁ -C ₄ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ alkynyloxy, CN, C ₁ -C ₄ alkyl, NH ₂ , N(C ₁ -C ₄ alkyl) ₂ , C ₁ -C ₄ alkylthio, phenyl, benzyl, phenoxy or benzyloxy, wherein alkyl, alkoxy, alkenyloxy, alkynyloxy, phenoxy, benzyloxy, phenyl and The benzyl group may be optionally substituted by one or more (for example one to five) groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy; each independently R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ and R ²² represent hydrogen, halogen, CN, OR ⁷ , C ₁ -C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₃ -C ₈ cycloalkyl, phenyl, pyridyl , benzyl, N(R ⁹ ) ₂ , CO ₂ R ⁷ , NR ⁹ COR ⁸ , CR ⁸ N-OR ⁷ , SH, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfin Mercapto, C ₁ -C ₈ alkylsulfonyl, phenylthio, phenylsulfinylene or phenylsulfonyl, wherein alkyl, alkenyl, cycloalkyl, phenyl, pyridyl and benzyl Alternatively, one or more (e.g., one to five) groups independently selected from halogen, CN, OR ⁷ , C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl; each independently R ⁷ represents hydrogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl.

Each of the respective independent R ⁸ represents hydrogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl.

Each of the respective independent R ⁹ represents hydrogen or C ₁ -C ₄ alkyl; wherein when two R ⁹ groups are attached to the same nitrogen atom, these groups may be the same or different; and wherein two R ^{When the 9} -position is attached to the same nitrogen atom, the two groups together with the nitrogen atom to which they are attached may form a ring B-1, B-2, B-3, B-4 or B-5, which is formed therein. The ring may be optionally substituted by one or more (e.g., one to five) groups independently selected from the group consisting of halogen, methyl, and halomethyl.

In one group of compounds, R ¹ represents C ₁ -C ₄ alkyl; D ¹ is CY ¹ ; D ² is CY ² ; D ³ is CY ³ ; D ⁴ is CY ⁴ ; each independently R ² , R ⁴ , R ⁵ and R ⁶ represent hydrogen, C ₁ -C ₄ alkyl or C ₂ -C ₄ alkenyl, wherein alkyl and alkenyl may be derived from one or more (eg one to five) from halogen, CN, methoxy and The groups independently selected from the halomethoxy group are optionally substituted; X represents X-3; Z ³ and Z ⁵ represent CR ¹⁰ R ¹¹ ; Z ⁴ represents CR ¹⁴ R ¹⁵ ; R ¹⁰ , R ¹¹ , R ¹⁴ and R ¹⁵ represents hydrogen; each independently Y ¹ , Y ² and Y ³ represent hydrogen or C ₁ -C ₄ alkyl; A ¹ represents ring A-1 or A-2; R ¹⁸ represents hydrogen, halogen, C ₁ -C ₄ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ alkynyloxy, CN, C ₁ -C ₄ alkyl, NH ₂ , N(C ₁ -C ₄ alkyl) ₂ , C ₁ -C ₄ alkylthio, phenyl, benzyl, phenoxy or benzyloxy, wherein alkyl, alkoxy, alkenyloxy, alkynyloxy, phenoxy, benzyloxy, phenyl and The benzyl group may be optionally substituted by one or more (for example one to five) groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy; R ¹⁹ represents hydrogen or C ₁ -C ₄ Alkyl; R ²⁰ represents hydrogen, halogen, OH, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, NH ₂ , C ₁ -C ₄ alkylthio, phenyl or benzyl, wherein Alkyl, cycloalkyl, phenyl and benzyl groups may be independently selected from one or more (for example one to five) halogen, CN, methyl, halomethyl, methoxy and halomethoxy groups. Selective substitution; R ²¹ represents hydrogen, halogen, OH, C ₁ -C ₄ alkyl, CO ₂ H, CO ₂ (C ₁ -C ₄ alkyl), C(C ₁ -C ₄ alkyl)NO ( C ₁ -C ₄ alkyl) or CHN-OH, wherein the alkyl group, the cycloalkyl group, the phenyl group and the benzyl group may be one or more (for example one to five) from halogen, CN, C ₁ -C ₄ alkyl, a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₄ alkoxy group and a C ₁ -C ₄ haloalkoxy group independently selected are optionally substituted; R ²² represents hydrogen or C ₁ -C ₄ alkane base.

Intermediates which can be used to prepare compounds of formula (I) are also part of the present invention.

Thus, in another aspect, the invention provides a compound of formula (VII)

Wherein R ²⁸ is halogen, and A ² , R ¹ , X, D ¹ , D ² and Y ^{3 are} as defined herein as the compound of formula (I); or a salt thereof or an N-oxide. For the compound of the formula (I), A ² , R ¹ , X, D ¹ , D ² and Y ^{3 are} preferably defined, and are also applicable to the compound of the formula (VII). R ²⁸ preferably represents chlorine, bromine or iodine.

In another aspect, the invention provides a compound of formula (IX)

Wherein A ² , R ¹ , X, D ¹ , D ² and Y ^{3 are} as defined herein as the compound of formula (I); or a salt thereof or an N-oxide. For the compound of the formula (I), A ² , R ¹ , X, D ¹ , D ² and Y ^{3 are} preferably defined, and are also applicable to the compound of the formula (IX).

In another aspect, the invention provides a compound of formula (X)

Wherein A ² , R ¹ , X, D ¹ , D ² and Y ³ are the same as defined in the compound of formula (I); or a salt thereof or an N-oxide. For the compound of the formula (I), A ² , R ¹ , X, D ¹ , D ² and Y ^{3 are} preferably defined, and are also applicable to the compound of the formula (X).

In another aspect, the invention provides a compound of formula (XI)

Wherein A ² , R ¹ , X, D ¹ , D ² and Y ³ are the same as defined in the compound of formula (I); or a salt thereof or an N-oxide. For the compound of the formula (I), A ² , R ¹ , X, D ¹ , D ² and Y ^{3 are} preferably defined, and are also applicable to the compound of the formula (XI).

In another aspect, the invention provides a compound of formula (XIII)

Wherein A ² , R ¹ , R ¹⁸ , X, D ¹ , D ² and Y ³ are the same as defined in the compound of the formula (I); or a salt thereof or an N-oxide. For the compound of the formula (I), A ² , R ¹ , R ¹⁸ , X, D ¹ , D ² and Y ^{3 are} preferably defined, and are also applicable to the compound of the formula (XIII).

In another aspect, the invention provides a compound of formula (XIV)

Wherein A ² , R ¹ , R ¹⁸ , X, D ¹ , D ² and Y ³ are the same as defined in the compound of the formula (I); or a salt thereof or an N-oxide. For the compound of the formula (I), A ² , R ¹ , R ¹⁸ , X, D ¹ , D ² and Y ^{3 are} preferably defined, and are also applicable to the compound of the formula (XIV).

The compounds of formula (I) may exist as different geometric isomers or optical isomers, or in different tautomeric forms. These can be separated and sequestered by well-known (usually chromatographic) techniques, and all such isomers and tautomers, as well as mixtures thereof, and isotopic forms, such as compounds containing heavy hydrogen, are Part of the invention. In particular, the carbon-nitrogen double bond of the compound of formula (I) allows the cis/trans isomers shown below:

The invention includes each of these isomers. The present invention can provide a compound of the formula (I) as one of these isomers or as a mixture of one or more isomers in any ratio. Likewise, the invention also includes isomers corresponding to the intermediates described herein, particularly compounds (VII), (IX), (X), (XI), (XIII) and (XIV). In addition, when the reaction scheme depicts the synthesis of a geometric isomer, the scheme also includes the synthesis of other possible geometric isomers. For example, Reaction Scheme A shown below also includes Reaction Scheme B:

The compounds in Tables 1 to 24 illustrate the compounds of formula (I) graphically.

Table X represents Table 1 (when X is 1), Table 2 (when X is 2), Table 3 (when X is 3), Table 4 (when X is 4), Table 5 (when X is 5 o'clock), Table 6 (when X is 6), Table 7 (when X is 7), Table 8 (when X is 8), Table 9 (when X is 9), Table 10 (when X is 10 o'clock), Table 11 (when X is 11), Table 12 (when X is 12), Table 13 (when X is 13), Table 14 (when X is 14), Table 15 (when X is 15 o'clock), Table 16 (when X is 16), Table 17 (when X is 17), Table 18 (when X is 18), Table 19 (when X is 19), Table 20 (when X is 20 o'clock), Table 21 (when X is 21), Table 22 (when X is 22), Table 23 (when X is 23), Table 24 (when X is 24), Table 25 (when X is 25 o'clock), Table 26 (when X is 26), Table 27 (when X is 27), Table 28 (when X is 28), Table 29 (when X is 29), Table 30 (when X is 30 o'clock), Table 31 (when X is 31), Table 32 (when X is 32), Table 33 (when X is 33), Table 34 (when X is 34), Table 35 (when X is 35 o'clock), Table 36 (when X is 36), and Table 37 (when X is 37).

Table 1: This table discloses compounds of formula (I-I) 1.001 to 1.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 2: This table discloses compounds of formula (I-II) 2.001 to 2.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 3: This table discloses compounds of formula (I-III) 3.001 to 3.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 4: This table discloses compounds of formula (I-IV) 4.001 to 4.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 5: This table discloses compounds of formula (I-V) 5.001 to 5.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 6: This table discloses compounds of formula (I-VI) 6.001 to 6.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 7: This table discloses compounds of formula (I-VII) 7.001 to 7.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 8: This table discloses compounds of formula (I-VIII) 8.001 to 8.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 9: This table discloses compounds of formula (I-IX) 9.001 to 9.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 10: This table discloses compounds of formula (I-X) from 10.001 to 10.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 11: This table discloses compounds of formula (I-XI) 11.001 to 11.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 12: This table discloses compounds of formula (I-XII) 12.001 to 12.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 13: This table discloses compounds of formula (I-XIII) 13.001 to 13.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 14: This table discloses compounds of formula (I-XIV) 14.001 to 14.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 15: This table discloses compounds of formula (I-XV) 15.001 to 15.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 16: This table discloses compounds of formula (I-XVI) 16.001 to 16.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 17: This table discloses compounds of formula (I-XVII) 17.001 to 17.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 18: This table discloses compounds of formula (I-XVIII) 18.001 to 18.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 19: This table discloses compounds of formula (I-XIX) 19.001 to 19.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 20: This table discloses compounds of formula (I-XX) 20.001 to 20.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 21: This table discloses compounds of formula (I-XXI) 21.001 to 21.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 22: This table discloses compounds of formula (I-XXII) 22.001 to 22.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 23: This table discloses compounds of formula (I-XXIII) 23.001 to 23.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 24: This table discloses compounds of formula (I-XXIV) 24.001 to 24.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 25: This table discloses compounds of formula (I-XXV) 25.001 to 25.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 26: This table discloses compounds of formula (I-XXVI) 26.001 to 26.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 27: This table discloses compounds of formula (I-XXVII) 27.001 to 27.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 28: This table discloses compounds of formula (I-XXVIII) 28.001 to 28.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 29: This table discloses compounds of formula (I-XXIX) 29.001 to 29.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 30: This table discloses compounds of formula (I-XXX) from 30.001 to 30.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 31: This table discloses compounds of formula (I-XXXI) 31.001 to 31.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 32: This table discloses compounds of formula (I-XXXII) 32.001 to 32.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 33: This table discloses compounds of formula (I-XXXIII) 33.001 to 33.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 34: This table discloses compounds of formula (I-XXXIV) 34.001 to 34.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 35: This table discloses compounds of formula (I-XXXV) 35.001 to 35.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 36: This table discloses compounds of formula (I-XXXVI) 36.001 to 36.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 37: This table discloses compounds of formula (I-XXXVII) 37.001 to 37.543

Wherein R ¹ , A ² , Y ¹ , Y ² and Y ³ have the special meanings given in the table.

Table 38 is illustrated Specific examples A ² and E.

Compounds in Table 39 illustrates compounds of formula (I) of which R1 is CH _3, and 38 A ² and E are defined as the table.

The compounds of Tables 1 to 39 contain all isomers, tautomers, and mixtures thereof, including the cis/trans isomers shown above.

The mixtures of the present invention can be made by a variety of methods and are illustrated in Schemes 1-15. The compounds depicted in the scheme also represent any isomers and tautomers, particularly geometric isomers derived from the oxime and oxime ether moieties.

Process 1:

1) A compound of the formula (I) is prepared by a compound of the formula (II) wherein X, D ¹ , D ² , Y ³ and A ¹ are the same as defined in the formula (I) A compound of formula (III) wherein A ² and R ¹ are as defined herein as the compound of formula (I) are reacted, and T ¹ and T ² are C ₁ -C ₈ alkoxy, or T ¹ and T ² Along with the carbon to which it is attached to form a carbonyl group, or an acetal or ketal functional group in the form of C(OC ₁ -C ₆ -alkylene-O), whereby the alkylene segment can be selectively The C ₁ -C ₆ alkyl group is mono- or tetra-substituted as shown in Scheme 1 .

A general description of the condensation reaction is provided below, and typical reaction conditions for such reactions can be found in Journal of Organic Chemistry, Vol. 52, No. 22, pp. 4978-84, 1987; Chemical & Pharmaceutical Bulletin, Bulletin of Chemistry and Pharmace, Vol. 51, No. 2, pp. 138-151, 2003; Organic Letters, Vol. 10, No. 2, pp. 285-288, 2008; Journal Of the American Chemical Society, Vol. 130, No. 12, pp. 4196-4201, 2008; Chemistry & Biology, Vol. 9, No. 1, p. 113- 129, 2002; Organic Preparations and Procedures International, Vol. 32, No. 2, pp. 153-159, 2000; Scientia Pharmaceutica, Science and Technology, Vol. 66, No. 1, Page 9-21, 1998; Journal of Medicinal Chemistry, Vol. 49, No. 17, pp. 5177-5186, 2006; Journal of Agricultural and Food Chemistry (Journal of Agriculture and Food Chemistry) , Vol. 38, No. 3, pp. 839-4 4, 1990; Tetrahedron: Asymmetry, Tetrahedron: Asymmetry, Vol. 8, No. 2, pp. 253-263, 1997; Journal of Medicinal Chemistry, Vol. 44, No. 21 , pp. 3339-3342, 2001; Bioorganic & Medicinal Chemistry Letters, Vol. 12, No. 3, pp. 341-344, 2002; US 2007032470; WO 07/058504; Journal of Organic Chemistry, Vol. 73, No. 5, pp. 2007-2010, 2008; Bioorganic & Medicinal Chemistry Letters, Vol. 19, No. 10, pp. 2683-2687, 2009; and Bioorganic & Medicinal Chemistry Letters, Vol. 19, No. 10, pp. 2654-2660, 2009.

Process 2:

2) Alternatively, as shown in Scheme 2 , a compound of formula (Ib) (which is a compound of formula (I) wherein Z ⁴ and Z ⁵ , Z ⁸ and Z ⁹ or Z ¹³ and Z ^{14 are} simultaneously methylene, And X' stands for X'-1, X'-2 or X'-3):

A compound of the formula (Ia) (that is, a compound of the formula (I), wherein Z ⁴ and Z ⁵ , Z ⁸ and Z ⁹ or Z ¹³ together with Z ¹⁴ form an ethynyl group, and X' is defined herein and a chemical formula ( The compound of Ib) is the same) prepared by catalytic hydrogenation in the presence of a metal catalyst such as palladium, nickel or platinum. The reaction is usually carried out in the presence of a solvent in a hydrogen atmosphere. In some cases it may be necessary to apply a pressure in the range of 1 to 100 bar. Suitable solvents for such reactions are alcohols (such as methanol or ethanol), cyclic ethers (such as dioxane or tetrahydrofuran) or esters (such as ethyl acetate). The temperature at which the reaction is carried out is usually from 0 ° C to the boiling point of the solvent. For an example of hydrogenation in the presence of a nickel catalyst, see Journal of Organometallic Chemistry, Vol. 333, No. 2, pp. 139-53, 1987. For examples of hydrogenation in the presence of palladium catalysts, see Tetrahedron (Tetrahedron), Vol. 63, No. 26, pp. 6015-6034, 2007 or Bioorganic & Medicinal Chemistry, No. 9. Volume 11, Issue 2863-2870, 2001. For examples of hydrogenation in the presence of platinum catalysts, see Journal of Organic Chemistry, Vol. 53 No. 2, pp. 386-90, 1988 or Journal of Medicinal Chemistry. Vol. 32, No. 8, pp. 1820-35, 1989.

Process 3:

3) Alternatively, as shown in Scheme 3 , a compound of formula (Id) is a compound of formula (I) wherein Z ⁴ , Z ⁸ and Z ¹⁴ represent CHR ¹⁰ and Z ⁵ , Z ⁹ and Z ¹⁴ represent CHR ¹¹ , and X' stands for X'-1, X'-2 or X'-3:

And each individually independent R ¹⁰ and R ¹¹ represent hydrogen, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, phenyl or CN, wherein the phenyl group is composed of one or more (eg one to Five) groups independently selected from halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy Optionally substituted and capable of permeating compound (Ic) (ie, a compound of formula (I) wherein Z ⁴ and Z ⁵ , Z ⁸ and Z ⁹ or Z ¹³ together with Z ¹⁴ form CR ¹⁰ =CR ¹¹ , X', R ¹⁰ and R ¹¹ are defined herein as defined for the compound of formula (Id)) by catalytic hydrogenation in the presence of a metal catalyst such as palladium, nickel or platinum. The reaction is usually carried out in the presence of a solvent in a hydrogen atmosphere. In some cases it may be necessary to apply a pressure in the range of 1 to 100 bar. Suitable solvents for such reactions are alcohols (such as methanol or ethanol), cyclic ethers (such as dioxane or tetrahydrofuran) or esters (such as ethyl acetate). The temperature at which the reaction is carried out is usually from 0 ° C to the boiling point of the solvent.

For an example of hydrogenation in the presence of a nickel catalyst, see Journal of Organic Chemistry, Vol. 69, No. 6, pp. 1959-1966, 2004. For an example of hydrogenation in the presence of a palladium catalyst, see Journal of Organic Chemistry, Vol. 74, No. 16, pp. 6072-6076, 2009. For examples of hydrogenation in the presence of platinum catalysts, see Organometallics, Vol. 5, No. 2, pp. 348-55, 1986.

Process 4:

4) The compound of formula (If) is a compound of formula (I) wherein Z ⁵ , Z ⁹ or Z ¹⁴ represents C=CR ¹² R ¹³ and X represents

A compound which can be obtained from the compound of (Ie), that is, a compound of the formula (I) wherein Z ⁵ , Z ⁹ or Z ¹⁴ represents a carbonyl group, and X is as defined for the compound of the formula (If).

This can be achieved by a number of techniques well known to the skilled person, including the Wittig reaction or the condensation reaction. The Wittig reaction involves a reaction between an aldehyde or a ketone, such as a ketone of the formula (Ie) and a phosphorus ylide. The phosphorus ylide is usually prepared by treating the cerium salt with a base, and the cerium salt is usually prepared from a triaryl phosphine and a halogen. Several improvements and modifications of the Wittig reaction are well known and are described, for example, in "March's Advanced Organic Chemistry: Reactions and Mechanisms and Structure" (Margie's Advanced Organic Chemistry: Reactions, Mechanisms and Structures) , sixth edition, 2007, and among the references therein. For specific reaction conditions, see Journal of the American Chemical Society, Vol. 131, No. 34, pp. 12344-12353, 2009; Journal of Medicinal Chemistry, Vol. 51 No. 22, pp. 7193-7204, 2008; Journal of Organic Chemistry, Vol. 74, No. 11, pp. 4166-4176, 2009.

Process 5:

(5) Further, as shown in Scheme 5 , the compound of the formula (I) is prepared by the formula (V) wherein X, Y ¹ , Y ² , Y ³ and A ^{1 are} defined herein and the formula (I) The compounds are the same, and R ²⁷ is halogen (especially chlorine, bromine or iodine) or a sulfonate group (for example mesylate, tosylate, triflate, phenyl sulfonate) The compound of nitrobenzenesulfonate or nonafluorobutyl sulfonate) is chemically reacted with a compound of formula (VI) wherein A ² and R ^{1 are} as defined herein as the compound of formula (I). Typical reaction conditions for, for example, such alkylation reactions can be found in the following references. These are further illustrated in the following literature: Chinese Journal of Chemistry, Vol. 27, No. 1, pp. 33-42, 2009; WO 09/049846; Journal of Antibiotics ( Journal of Antibiotics, Vol. 61, No. 10, pp. 603-614, 2008; Bioorganic & Medicinal Chemistry Letters, Vol. 18, No. 24, pp. 6471-6475, 2008; Journal of Medicinal Chemistry, Vol. 51, No. 15, pp. 4601-4608, 2008; WO 06/123145, Archiv der Pharmazie (Pharmaceutical Literature, Weinheim, Germany), Vol. 340 4, pp. 202-208, 2007; Synthetic Communications, Vol. 37, No. 7, pp. 1155-1165, 2007; Russian Journal of Organic Chemistry, No. Volume 42, Number 5, pp. 735-738, 2006; Bioinorganic Chemistry and Applications, Vol. 1, Nos. 3-4, pp. 299-308, 2003; Synthetic Communications ( Synthetic Communications), Vol. 28, No. 14, Page 2621-2633, 1998; Synthetic Communications, Vol. 19, No. 18, pp. 3129-38, 1989.

(6) The compound of the formula (V) can be produced from the compound of the formula (IV). Such changes can be achieved through many conditions familiar to professionals.

Process 6:

(7) Further, as shown in Scheme 6 , the compound of formula (I) is prepared by formula (VII) (wherein A ² , R ¹ , X, D ¹ , D ² and Y ^{3 are} defined herein) The compound of the formula (I) is the same, and the compound of R ²⁸ is a halogen, particularly chlorine, bromine or iodine) and the formula (VIII) (wherein A ^{1 is} as defined herein as the compound of the formula (I), and M is an organometallic The compound of the residue) reacts. This can be achieved by a number of techniques well known to the skilled person, including Suzuki, Suzuki, Stille & Negishi. For examples and specific conditions of the Stille reaction, see Bioorganic & Medicinal Chemistry Letters, Vol. 19, No. 19, pp. 5689-5692, 2009; Journal of Organic Chemistry (Journal of Organic Chemistry), Vol. 73, No. 12, pp. 4491-4495, 2008; Journal of the American Chemical Society, Vol. 129, No. 3, pp. 490-491, 2007 Year; or Journal of Organic Chemistry, Vol. 75, No. 2, pp. 424-433, 2010. For examples and specific conditions of the Negishi reaction, please refer to the European Journal of Inorganic Chemistry, No. 26, pp. 4101-4110, 2008; Tetrahedron Letters (Tetrahedron Communication), No. 50 Vol. 38, pp. 5329-5331, 2009; Tetrahedron Letters (Tetrahedron Communication), Vol. 51, No. 2, pp. 357-359, 2010; or Tetrahedron Letters (Tetrahedron Communication), Vol. 51, No. 19, pp. 2657-2659, 2010. Examples and specific conditions for the Suzuki reaction can be found in Organic Letters, Vol. 11, No. 2, pp. 345-347, 2009; Journal of the American Chemical Society (Journal of the American Chemical Society) , Vol. 131, No. 20, pp. 6961-6963, 2009; Synthesis (Synthesis), No. 1, pp. 85-90, 2010; or Heterocycles (Heterocyclic), Volume 80, Number 1 , pp. 359-368.

Process 7:

(8) A compound of the formula (Ig), which is a compound of the formula (I), wherein A ¹ is A-2, which can be obtained from an anthracene of the formula (X), wherein A ² , R ¹ , X, D ¹ , D ² and Y ^{3 are} as defined herein as the compound of formula (I). This type of transformation can be achieved through many conditions familiar to professionals. For specific examples and conditions, please refer to the Chemistry-A European Journal, Vol. 16 No. 1, pp. 89-94, S89/1-S89/10, 2010; Tetrahedron Letters (four sides) Bulletin), Vol. 50, No. 49, pp. 6818-6822, 2009; Bioorganic & Medicinal Chemistry Letters, Vol. 15, No. 12, pp. 2990-2993, 2005; Synthetic Communications, Vol. 27, No. 14, pp. 2521-2526, 1997; Journal of Combinatorial Chemistry, Vol. 7, No. 4, pp. 517-519, 2005 And "Bioorganic & Medicinal Chemistry Letters", Vol. 15, No. 12, pp. 2990-2993, 2005.

(9) The oxime of the formula (X) can be prepared from a nitrile of the formula (IX) wherein A ² , R ¹ , X, D ¹ , D ² and Y ^{3 are} defined herein and the formula (I) The compounds are the same. Typical conditions for this transformation can be found in the following journal article: Bioorganic & Medicinal Chemistry, Vol. 17, No. 18, pp. 6651-6658, 2009; Bioorganic & Medicinal Chemistry Letters (Bioorganic) Journal of Medicinal Chemistry, Vol. 19, No. 8, pp. 2277-2281, 2009; Journal of Medicinal Chemistry, Vol. 51, No. 6, pp. 1719-1729, 2008; or Journal of Medicinal Chemistry, Vol. 50, No. 26, pp. 6535-6544, 2007.

Process 8:

(10) A compound of the formula (Ih) which is a compound of the formula (I) wherein A ¹ is A-4 and R ²² is hydrogen, which can be obtained from a compound of the formula (XIV) wherein A ² , R ¹ , X, D ¹ , D ² , Y ³ and R ^{18 are} as defined herein as the compound of formula (I) and the oxime of formula (XV), wherein R ^{20 is} as defined herein as the compound of formula (I). Typical conditions for this transition are detailed in the following journal articles: Tetrahedron Letters (Tetrahedron Newsletter), Vol. 50, No. 49, pp. 6818-6822, 2009; Chemistry-A European Journal (Chemistry-European Journal), Vol. 15 No. 20, pp. 5006-5011, 2009; Journal of Organic Chemistry, Vol. 74, No. 12, pp. 4646-4649, 2009; or Synlett, No. 19 , page 3036-3040, 2008. Chemical formula (XV) anthraquinones can be obtained commercially or prepared by methods familiar to those skilled in the art.

(11) A compound of formula (XIV) can be prepared from the oxidation of a compound of formula (XIII) wherein A ² , R ¹ , X, D ¹ , D ² , Y ³ and R ^{18 are} defined herein and formula The compounds of (I) are the same. This type of oxidation can be achieved by many conditions familiar to the professional. For specific reaction conditions, please refer to Journal of the American Chemical Society, Vol. 132, No. 8, pp. 2532-2533, 2010; Journal of Organic Chemistry, 74th Vol. 15, No. 5750-5753, 2009; or Tetrahedron (Tetrahedron), Vol. 64, No. 29, pp. 7008-7014, 2008.

(12) A compound of the formula (XIII) can be prepared from an aldehyde of the formula (XI) wherein A ² , R ¹ , X, D ¹ , D ² and Y ^{3 are} defined herein as a compound of the formula (I) It is the same as the compound of the formula (XII), wherein R ^{18 is} as defined herein as the compound of the formula (I). Typical conditions for such transformations can be found in Tetrahedron (Tetrahedron), Vol. 64, No. 29, pp. 7008-7014, 2008; Journal of Organic Chemistry, Vol. 72, No. 20, Page 7783-7786, 2007; or "Organic Letters", Vol. 9, No. 6, pp. 1169-1171, 2007.

Process 9:

(13) A compound of the formula (IIa), which is a compound of the formula (II), wherein Z ⁴ and Z ⁵ , Z ⁸ and Z ⁹ or both Z ¹³ and Z ¹⁴ are methylene groups, and X′ is defined as a chemical formula (Ia) The compound is the same and can be obtained from a compound of (XVIII) wherein D ¹ , D ² , Y ³ and A ^{1 are} as defined herein as the compound of formula (I), and X' is defined herein and formula (Ia) The compounds are identical (obtained by cleavage of the o-xylylene imine protecting group). An example of such deprotection can be found in Greene, TW, Wuts, PGN, "Protective Groups in Organic Synthesis", published by John Wiley & Sons, Inc., 2006.

(14) A compound of formula (XVIII) can be obtained from the catalytic hydrogenation of a compound of formula (XVII) wherein D ¹ , D ² , Y ³ and A ^{1 are} as defined herein as the compound of formula (I), and X' is defined herein as the compound of formula (Ia). The reaction can be carried out in accordance with Procedure 2, as shown in Scheme 2 .

(15) A compound of the formula (XVII) can be prepared from a compound of the formula (XVI) wherein D ¹ , D ² , Y ³ and A ^{1 are} as defined herein as the compound of the formula (I), and X' The definition is the same as the compound of the formula (Ia) (obtained by a Mitsunobu reaction). The Mitsunobu reaction involves the presence of a primary or secondary alcohol in the presence of a dialkyl azodicarboxylate and a trialkylphosphine or a triarylphosphine, from a nucleophilic agent (eg, N-hydroxy phthalic acid). The reaction substituted with dimethylimine) is shown in Scheme 9 . Several improvements and modifications of the Mitsunobu reaction are widely known and are described, for example, in "March's Advanced Organic Chemistry: Reaction, Mechanisms and Structure", No. 3, Advanced Chemistry of Machi: Reactions, Mechanisms and Structures, Six editions, 2007, and among the references therein. For specific reaction conditions, please refer to: Organic Preparations and Procedures International, Vol. 26, No. 1, pp. 111-13, 1994; Organic Letters, Vol. 11. No. 9, pp. 2019-2022, 2009; Tetrahedron Letters (Tetrahedron Newsletter), Vol. 48, No. 4, pp. 647-650, 2007; or Journal of Organic Chemistry , Vol. 70, No. 17, pp. 6995-6998, 2005.

Process 10:

(16) A compound of the formula (Ia) can be prepared from a compound of the formula (VI) wherein A ² and R ^{1 are} defined herein as a compound of the formula (I) and a compound of the formula (Va) (ie, formula (V) A compound wherein Z ⁴ and Z ⁵ , Z ⁸ and Z ⁹ or Z ¹³ together with Z ¹⁴ form an acetylene group, and X' is defined herein to be the same as the compound of formula (Ia). The alkylation reaction can be carried out in accordance with procedure 5, as shown in Scheme 5 .

(17) A compound of the formula (Va) can be prepared from a compound of the formula (XVI) wherein D ¹ , D ² , Y ³ and A ^{2 are} as defined herein as the compound of the formula (I), and X' The definition is the same as the compound of the formula (Ia), and R ²⁷ is the same as the compound of the formula (V). Such changes can be achieved through many conditions familiar to professionals.

(18) Further, as shown in Scheme 10 , the compound of the formula (Ia) may be the same as the compound of the formula (I) wherein D ¹ , D ² , Y ³ and A ^{1 are} defined herein, and R ^{28 is} defined herein as the compound of formula (VII)) and a compound of formula (XX) wherein A ² and R ^{1 are} as defined herein as the compound of formula (I), and X' is defined as formula (Ia) The compound is the same) prepared by the Sonogashira reaction. The reaction can be carried out in a palladium catalyst (such as tetrakistriphenylphosphine palladium (II) or dichlorobis(triphenylphosphine)palladium (II)), cuprous salts (such as cuprous chloride, cuprous bromide or iodine). The cuprous) is carried out in the presence of a base such as triethylamine, ethyldiisopropylamine, diethylamine, diisopropylamine or dicyclohexylamine. Alkali can also be used as a solvent if possible. Examples of other suitable solvents are N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dimethyl hydrazine, dioxane or tetrahydrofuran. The temperature at which the reaction is carried out is usually from 0 ° C to the boiling point of the solvent. An example of a Sonogashira reaction can be found in Handbook of Organopalladium Chemistry for Organic Synthesis, 2002, Vol. 1, pp. 493-529.

(19) A compound of the formula (XX) can be produced from a compound of the formula (VI) and a compound of (XIX) wherein X' is as defined herein as the compound of the formula (Ia), and R ^{27 is} as defined herein. The compound of (V) is the same. Many of the above compounds are described in the literature and are commercially available or can be prepared by methods familiar to those skilled in the art.

Process 11:

(20) A compound of the formula (Ij), which is a compound of the formula (I), wherein A ¹ is A-1, R ²² is hydrogen or methyl, R ²⁰ is methyl or ethyl, Z ⁴ and Z ⁵ , Z ⁸ and Z ⁹ or Z ¹³ together with Z ¹⁴ form an acetylene group, and X' is defined herein as the compound of formula (Ia), which may be a compound of formula (XXV) (wherein D ¹ , D ² and Y ^{3 are} herein) Definitions are the same as the compound of formula (I), R ²² is hydrogen or methyl, R ²⁰ is methyl or ethyl, R ^{18 is} as defined herein as the compound of formula (I), and R ^{28 is} defined herein and formula ( The compound of VII) is the same as the compound of formula (XX) (wherein A and R ^{1 are} as defined herein as the compound of formula (I), and X' is defined herein as the compound of formula (Ia)) Prepared. The reaction can be carried out in a palladium catalyst (such as tetrakistriphenylphosphine palladium (II) or dichlorobis(triphenylphosphine)palladium (II)), cuprous salts (such as cuprous chloride, cuprous bromide or iodine). The cuprous) is carried out in the presence of a base such as triethylamine, ethyldiisopropylamine, diethylamine, diisopropylamine or dicyclohexylamine. Alkali can also be used as a solvent if possible. Examples of other suitable solvents are N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dimethyl hydrazine, dioxane or tetrahydrofuran. The temperature at which the reaction is carried out is usually from 0 ° C to the boiling point of the solvent. An example of a Sonogashira reaction can be found in Handbook of Organopalladium Chemistry for Organic Synthesis, 2002, Vol. 1, pp. 493-529.

(21) A compound of formula (XXV) can be prepared from a compound of formula (XXIV) wherein D ¹ , D ² and Y ^{3 are} as defined herein as the compound of formula (I) wherein R ²² is hydrogen or And R ²⁰ is methyl or ethyl, and R ^{28 is} as defined herein as the compound of formula (VII). Such changes can be achieved through many conditions familiar to professionals.

(22) A compound of the formula (XXIV) can be prepared from a compound of the formula (XXIII) wherein D ¹ , D ² and Y ^{3 are} as defined herein as the compound of the formula (I), and R ²⁰ is methyl or B. And R ^{28 is} as defined herein as the compound of formula (VII) (via trimethylsulfonium triflate and H in 1,2-dichloroethane The reaction of nig's base at reflux temperature is described in "Chem. Eur. J.", European Journal of Chemistry, 2009, Vol. 15, page 6811-6814.

(23) A compound of the formula (XXIII) can be prepared from a compound of the formula (XXII) wherein D ¹ , D ² and Y ^{3 are} as defined herein as the compound of the formula (I), and R ^{28 is} defined herein and a formula The compound of (VII) is the same. Such changes can be achieved through many conditions familiar to professionals.

Process 12:

(24) A compound of the formula (XVI) can be prepared by reacting a compound of the formula (XXI) with a compound of the formula (XXVI) via a sorghum (Sonogashira), wherein X' is defined herein to be the same as the compound of the formula (Ia). The Sonogashira reaction can be performed in accordance with procedure 20, as shown in Scheme 11 .

Process 13:

(25) The compound of the formula (Ic) may be a compound of the formula (Vb) (i.e., a compound of the formula (V) wherein Z ⁴ and Z ⁵ , Z ⁸ and Z ⁹ or Z ¹³ together with Z ¹⁴ form CR ¹⁰ =CR ¹¹ And X' is defined as a compound of the formula (Ia), and R ¹⁰ and R ^{11 are} defined herein as those of the formula (I)) and the compound of the formula (VI) is prepared. The alkylation reaction can be carried out in accordance with procedure 5, as shown in Scheme 5 .

(26) A compound of the formula (Vb) can be prepared from a compound of the formula (XXVII) in a multi-step synthesis wherein D ¹ , D ² , Y ³ and W are as defined herein as the compound of the formula (I), and R ^{11 is} as defined herein as defined for the compound of formula (I). This can be achieved by a few techniques well known to the professional, including the first step of the Wittig reaction or the Horner-Wadsworth Emmons reaction, and more. Further transformation. See process 14 for a more specific example.

Process 14:

(27) a compound of the formula (Vc), that is, when X is X-3, Z ¹ is a methylene group, and Z ² together with Z ³ forms a compound of CR ¹⁰ =CR ¹¹ , D ¹ , D ² , Y ³ and A ^{1 is} defined herein as a compound of formula (I), and R ¹⁰ and R ^{11 are} defined herein as compounds of formula (Ic), which are prepared via the preparation of a compound of (XXX) wherein D ¹ , D ² , Y ³ are A ^{1 is} defined herein as a compound of formula (I), and R ¹⁰ and R ^{11 are} as defined herein as the compound of formula (Ic). Such changes can be achieved through many conditions familiar to professionals.

(28) A compound of the formula (XXX) can be prepared from a compound of the formula (XXIX) wherein D ¹ , D ² , Y ³ and A ^{1 are} as defined herein as the compound of the formula (I), R ¹⁰ and R ^{11 is} defined herein to be the same as the compound of the formula (Ic), and R ³¹ represents a C ₁ -C ₄ alkyl group (obtained by reduction of a metal hydride such as lithium aluminum hydride or diisobutyl aluminum hydride) . Examples of such reductions can be found in Journal of Combinatorial Chemistry, Vol. 7, No. 6, p. 958-967, 2005. This reaction is usually carried out at a temperature between -100 and 20 ° C in the presence of a solvent.

(29) A compound of the formula (XXIX) can be prepared from a compound of the formula (XXVII) and a phosphonate of the formula (XXVIII) wherein R ³¹ , R ³² and R ³³ are Horner-Waworth-Emmons (Horner-Wadsworth Emmons) C ₁ -C ₄ alkyl group in the reaction. This reaction is carried out in the presence of a base. Suitable bases include metal hydrides such as calcium hydride, lithium hydride, sodium hydride or potassium hydride, organometallic compounds such as butyllithium, or organic bases such as triethylamine or ethyldiisopropylate combined with lithium chloride. Amine. For examples, see the following journal article: Bioorganic & Medicinal Chemistry, Vol. 11, No. 18, pp. 4015-4026, 2003; Synthesis (Synthesis), No. 4, p. 283 -5, 1981; Journal of Medicinal Chemistry, Vol. 53 No. 3, pp. 1200-1210, 2010.

Process 15:

(30) The compound of the formula (Ik) is a compound of the formula (I) (wherein Z ¹ , Z ³ , Z ⁶ or Z ¹⁴ represents CH(OH), and X''' represents X'''-1, X '''-2, X'''-3 or X'''-4

Wherein Z ¹ , Z ³ , Z ⁴ , Z ⁶ , Z ⁷ , Z ⁸ , Z ¹⁰ , Z ¹¹ , Z ¹² and Z ^{13 are} as defined herein as the compound of formula (I)) may be an aldehyde of formula (XXXIII) ( Wherein A ² and R ¹ are the same as the compound of formula (I), X′′′ is defined as a compound of formula (Ik) and a compound of formula (XXIa) (ie is a compound of formula (XXI) wherein R ²⁸ is R ^28' wherein ^R28' is prepared from chlorine, bromine or iodine. Such a conversion can be achieved by a halogen metal displacement reaction in a (XXIa) compound with a suitable reagent such as magnesium, isopropylmagnesium chloride or isopropylmagnesium bromide or n-butyllithium, and between such metallated pyridines. Formed in the reaction with a compound of formula (XXXIII). An example of this transformation can be found in the following journal article: Angewandte Chemie, International Edition, Vol. 43, No. 25, pp. 3333-3336, 2004; Organic Letters (Organic Chemistry Newsletter), Vol. 6, No. 26, pp. 4905-4907, 2004; Journal of the American Chemical Society, Vol. 130, No. 38, pp. 12592-12593, 2008; Organic Letters ( Organic Chemistry Newsletter, Vol. 11 No. 20, pp. 4540-4543, 2009.

The compounds of formula (Ik) are particularly useful as intermediates for many other compounds in which the hydroxyl groups formed are converted to other functional groups such as carbonyl, fluorine or chlorine. Such changes can be achieved through many conditions familiar to professionals.

(31) A compound of the formula (XXXIII) can be produced by oxidizing a compound of the formula (XXXII). This type of oxidation can be achieved by many conditions familiar to the professional. For specific reaction conditions, see Organic & Biomolecular Chemistry, Vol. 6, No. 21, pp. 4036-4040, 2008; Bioorganic & Medicinal Chemistry Letters (Bioorganic & Medicinal Chemistry Newsletter) , Vol. 19, No. 13, pp. 3627-3631, 2009; Cambridge, UK, Chemical Communications, No. 37, pp. 5618-5620, 2009; Synthesis (Synthesis), No. 1, Page 91-97, 2010.

(32) A compound of the formula (XXXII) can be prepared from a compound of the formula (VI) and a compound of the formula (XXXI) wherein X'' is defined herein to be the same as the compound of the formula (Ik), and R ^{27 is} defined herein. The compounds of formula (V) are the same. Many of the above compounds are described in the literature and are commercially available or can be prepared by methods familiar to those skilled in the art. This alkylation reaction can be carried out in accordance with procedure 5, as shown in Scheme 5 .

The preparation of the compounds of formula (VI), (IX) and (XI) can be carried out in accordance with procedures 2 , 16 , 17, 18 and 19 as shown in Scheme 2 and Scheme 10 .

Typical conditions for the condensation reaction are as follows: This applies to Procedure 1.

Depending on the nature of the reactants and products, different stoichiometry schemes may be employed for these reactions. An excess of electrophile, nucleophile or equivalent molar number can be selected. It is preferred to use an electrophile or nucleophile compound in an amount equal to the molar amount.

The reaction may be carried out efficiently, whether or not inert organic, inorganic solvents are present or in the presence of a mixture of such solvents. It should preferably be carried out in one or more solvents. Preferred solvents include the following aliphatic or aromatic hydrocarbons (optionally substituted with one or more halogen atoms) such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzene, toluene, xylene, chlorine Benzene, dichlorobenzene, dichloromethane, chloroform, 1,2-dichloroethane or carbon tetrachloride, ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, tetrahydrofuran, 1, 4-dioxane, dimethoxyethane or diethylene glycol dimethyl ether, ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone or methyl isobutyl ketone, acid And esters such as acetic acid, ethyl acetate or methyl acetate, aprotic polar solvents such as acetonitrile, propionitrile, dimethylformamide, dimethylacetamide, N-methyl-pyrrolidone, dimethyl hydrazine, Cyclobutane, DMPU, or pyridine and picoline. Solvents which may be used include water and alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol, pentanol, isoamyl alcohol, hexanol, trifluoroethanol, ethylene glycol or Methoxyethanol.

The reaction can be carried out between -20 and 250 degrees Celsius, preferably between 0 and 100 degrees Celsius. In some cases, the reaction mixture can be heated to produce reflux.

Where appropriate, compounds may be employed in the form of free compounds, or in the form of salts, including acetates, trifluoroacetic acid, propionic acid, benzoates, oxalates, methanesulfonates, benzenesulfonic acids. Salt, p-toluenesulfonate, triflate, fluoride, chloride, bromide, iodide, sulphate, hydrogen sulphate or nitrate, optionally in the form of a double salt.

In the absence of acid, the reaction can still be carried out using free compounds. Alternatively, the reaction can be carried out in the case where the acid is in an amount capable of initiating a catalytic reaction, in a stoichiometric amount or in excess. Acids which may be used include acetic acid, propionic acid, oxalic acid, trifluoroacetic acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, methanesulfonic acid, p-toluenesulfonic acid, sulfuric acid, sodium hydrogen sulfate, and phosphoric acid. The reaction can also be carried out in an anhydrous solvent system in the presence of a desiccant such as sodium sulfate or magnesium sulfate, potassium carbonate or molecular sieves.

If the two substituents of the carbon atom in the oxime or oxime ether functional group are different from each other, the condensation reaction results in the mixing of the E and Z oxime (ether) products. The condensation product may be completely E (an ether) product or completely Z oxime (ether) product.

The condensation reaction can be carried out under reduced pressure, normal pressure or pressurized conditions. However, the reaction is preferably carried out under normal pressure.

Typical conditions for the alkylation reaction are as follows: This applies to procedures 16, 25 and 32.

Depending on the nature of the reactants and products, different stoichiometry schemes may be employed for these reactions. Excess electrophiles, nucleophiles, or none can be used. Generally, it is preferred to use an electrophile or nucleophile compound in an amount equal to the molar amount.

The reaction can be carried out in the presence or absence of a solvent or solvent mixture. Preferred solvents include the following aliphatic or aromatic hydrocarbons (optionally substituted with one or more halogen atoms) such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzene, toluene, xylene, Chlorobenzene, dichlorobenzene, dichloromethane, chloroform, 1,2-dichloroethane or carbon tetrachloride, ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, tetrahydrofuran, 1 , 4-dioxane, dimethoxyethane or diethylene glycol dimethyl ether, ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone or methyl isobutyl ketone, acid And esters such as acetic acid, ethyl acetate or methyl acetate, aprotic polar solvents such as acetonitrile, propionitrile, dimethylformamide, dimethylacetamide, N-methyl-pyrrolidone, dimethyl hydrazine, Cyclobutane, DMPU, or pyridine and picoline. Solvents which may be used include water and alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol, pentanol, isoamyl alcohol, hexanol, trifluoroethanol, ethylene. Alcohol or methoxyethanol.

The reaction can be carried out in a two phase system comprising an organic solvent which is not compatible with water, such as toluene, dichloromethane, dichloroethylene, and an aqueous solvent such as water. This reaction can be carried out in the presence of a phase transfer catalyst such as tetra-n-butylammonium bromide (TBAB), tetradecyldimethylbenzylammonium chloride (TDMBAC), N-benzyltrimethyl Ammonium hydroxide, and a stoichiometric aqueous solution of sodium hydroxide or potassium hydroxide. The two-phase reaction can be carried out with or without ultrasonic treatment.

The reaction can be carried out between -100 and 250 degrees Celsius. It is preferred to be between 0 and 100 degrees Celsius.

Alternatively, organic or inorganic bases such as alkali and alkaline earth acetates, guanamines, carbonates, hydrogencarbonates, hydrides, hydroxides or alcoholates such as sodium acetate, potassium acetate, cesium acetate or calcium acetate, carbonic acid may be used. Sodium, potassium carbonate, cesium carbonate or calcium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, cesium hydrogencarbonate or calcium hydrogencarbonate, sodium hydride, potassium hydride, cesium hydride or calcium hydride, sodium amination, potassium amide, alum Or aminated calcium, sodium hydroxide, potassium hydroxide, barium hydroxide or calcium hydroxide, sodium methoxide, potassium methoxide, methanol or calcium methoxide, sodium ethoxide, potassium ethoxide, ethanol or calcium ethoxide, n-, i- , s- or t-butanol sodium, potassium, barium or calcium, triethylamine, tripropylamine, tributylamine, diisopropylethylamine, N,N-dimethylcyclohexylamine, N-methyldi Cyclohexylamine, N,N-dimethylaniline, N,N-diethylaniline, N,N-dimethylbenzylamine, N,N-diethylbenzylamine, pyridine, 2-methyl Pyridine, 3-methylpyridine, 4-methylpyridine, 2,6-lutidine, 2,4,6-trimethylpyridine, 4-dimethylaminopyridine, N-methylpiperidine, N -ethylpiperidine, N-methylmorpholine, N-ethylmorpholine, N,N -Dimethylpiperazine, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8-diaza-7-bicyclo[5.4.0]undecene (DBU) 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 1-tert-butyl-2,2,2-tris(1-pyrrolidine)phosphazene (BTPP), 1 -tert-butyl-2,2,2-tris(dimethylamino)phosphazene, sodium hexamethyldisilazane, potassium hexamethyldisilazide, lithium diisopropylamide, ethylmagnesium chloride, Isopropyl magnesium chloride.

The alkylation can be carried out under reduced pressure, atmospheric pressure or pressurized conditions. However, the reaction is preferably carried out under normal pressure.

The products of Schemes 1) to 15) may need to be purified by chromatography, crystallization or other purification methods well known to those skilled in the art.

The compounds of formula (I) to formula (XXXIII) and, where applicable, their tautomers (if applicable) may also be obtained in the form of hydrates and/or include other solvents, such as solvents used to crystallize the solid form compounds.

It has now been found that, for practical purposes, the compounds of formula (I) of the present invention have a very advantageous range of activity for protecting utility plants against diseases caused by phytopathogenic microorganisms such as fungi, bacteria or viruses.

The invention is therefore also related to the control or control of useful plants by phytopathogenic microorganism infection therapy, wherein the compound of formula (I) is applied as an active ingredient to the plant itself, to its site or to its location. According to the present invention, the compound of the formula (I) can be obtained with a low application rate, the plant is well tolerated, and does not cause environmental hazards. It has excellent therapeutic, preventive and systemic properties and is used to protect a large number of practical plants. The compound of formula (I) can be used to inhibit or eliminate diseases of plants or plant parts (fruits, calves, leaves, stems, tubers and roots) which occur in different crops of practical plants, and at the same time protect the parts of plants which grow later (eg from infection by plant pathogenic microorganisms).

The compound of formula (I) may also be used as a dressing to treat the reproductive parts of plants, especially seeds (fruits, tubers, grains) and plant cuttings (eg rice) to protect plants from fungal infections and from soil. Infested by phytopathogenic fungi.

Further, the compound of the formula (I) in the present invention can be used for inhibiting fungi in related fields, such as technical materials for protecting food storage and hygiene management, including wood and wood related technical products.

For example, the compound of formula (I) is effective against the following class of phytopathogenic fungi: Fungi imperfecti (eg Botrytis, Pyricularia, wheat flax) (Helminthosporium), Fusarium, Septoria, Cercospora and Alternaria, and Basidiomycetes (eg potato black scorpion) Rhizoctonia, Hemileia, Puccinia, etc.). In addition, it is also possible to control Ascomycetes classes (eg, Venturia and Erysiphe, Podosphaera, Monilinia, grapes) Phytophthora (Uncinula, etc.) and Oomycetes classes (such as Phytophthora, Pythium, Plasmopara, etc.). Within the scope of the present invention, the following practical plant species are typically protected: cereal plants (including wheat, barley, rye, oats, rice, corn, sorghum, etc.), beets (sugar beets and beets) ), pear fruit, stone fruit and softfruit (including apple, pear, plum, peach, almond, cherry, strawberry, raspberry and blackberry), legumes (including beans, lentils, peas and soybeans, etc.) , oil plants (including rapeseed, mustard, poppy, olive, sunflower, coconut, ramie, cocoa and peanuts), melons (including pumpkin, cucumber and melon), fiber plants (including cotton, flax, hemp and Jute, etc.), citrus plants (including orange, lemon, grapefruit and oranges), vegetables (including spinach, lettuce, asparagus, kale, carrots, onions, tomatoes, potatoes and peppers, etc.), medlar (including cheese) Pear, cinnamon and camphor, etc. or other plants such as tobacco, nuts, coffee, eggplant, sugar cane, tea, pepper, vines, hops, bananas, natural rubber plants and ornamental plants.

The term "practical plant" can be understood to include crops that can be tolerant to the following herbicides, such as bromoxynil or herbicides, such as HPPD inhibitors, ALS inhibitors such as fluoropyrimidine, after modification using conventional breeding or genetic engineering methods. Sulfonamide, fluorosulfuron and triflusulfuron, EPSPS (5-enol-pyrovyl shikimate-3-phosphate synthase) inhibitor, GS (glutamate synthase) inhibitor or PPO (pro-porphyrinogen oxidase) inhibitor). In the market, there are already examples of crops that are resistant to imidazolinones (such as imazamox) by conventional methods of breeding (mutation induced) and named Summer rapeseed (canola). In the market, there are already examples of crops that are genetically engineered and resistant to herbicides or herbicides, including those resistant to glyphosate and glufosinate. The product name is Herculex with .

The term "practical plant" is understood to include the ability to synthesize one or more selective acting toxins (eg known as from toxin-producing bacteria, particularly Bacillus) after transformation using recombinant DNA techniques. Practical plants.

Examples of such plants are: (Cryana (b) toxin corn variety); YieldGard (Corn IIIB (b1) toxin corn variety); YieldGard (a corn variety showing CryIA (b) and CryIIIB (b1) toxins); (a corn variety showing Cry9(c) toxin); (A corn variety showing CryIF (a2) toxin and glufosinate N-acetyltransferase enzyme (PAT) to glufosinate-tolerant herbicide tolerance); NuCOTN (a cotton variety showing CryIA(c) toxins); Bollgard (a cotton variety showing CryIA(c) toxins); Bollgard (a cotton variety that expresses CryIA (c) and CryIIA (b) toxins); (a cotton variety showing VIP toxins); (potato varieties of CryIIIA toxin); NatureGard GT Advantage (GA21 glyphosate tolerance characteristics), CB Advantage (Bt11 corn borer (CB) characteristics), RW (corn rootworm characteristics) and .

The term "practical plant" can be understood to include the selective role of synthesis after transformation using recombinant DNA technology (such as the so-called "Pathogenesis-Related Proteins" (PRPs, see EP-A- 0 392 225)) A practical plant that is resistant to pathogenic substances. Exemplary sources of such anti-pathogenic agents and transgenic plants which can synthesize such anti-pathogenic agents are for example: EP-A-0 392 225, WO 95/33818 and EP-A-0 353 191. Such methods of producing transgenic plants are generally well known to those skilled in the art and are mentioned, for example, in the above publications.

The term "place" of a practical plant can be understood here to include a practical plant growth site, a planting site for a practical plant propagation material, or a practical plant propagation material to be sown into the soil. An example of such a place is the field, where the crop grows.

The term "plant propagation material" is understood to mean a plant breeding site (such as a seed) that can be used to propagate the seed of the plant, as well as vegetative propagation material such as cuttings or tubers, such as potatoes. Materials that may be mentioned such as seeds (narrow), roots, fruits, tubers, bulbs, underground stems and various parts of plants. It is also possible to mention sprouted plants and young plants that will be transplanted after germination or from soil germination. These young plants can be protected by whole plant or partial soaking treatment prior to transplantation. Preferably, "plant propagation material" is understood to mean a seed.

When the compound of the formula (I) is used, it may be used in an unmodified form or preferably used together with a carrier and an adjuvant conventionally used in the field of formulation.

Therefore, the present invention is also related to the control or control of a composition of a phytopathogenic microorganism (including a compound of the formula (I) and an inert carrier), and also to a therapy for controlling or controlling the infection of a practical plant by a plant pathogenic microorganism, which comprises as an active ingredient The composition of the compound of formula (I) and an inert carrier will be applied to the crop itself, its location or its location.

For this purpose, the compound of the formula (I) and the inert carrier can be conveniently formulated into an emulsifiable concentrate, a plaster, a solution which can be directly sprayed or diluted, a diluted emulsion, a wettable powder, a soluble powder, or the like, in a known manner. Powders, granules, and capsules coated with a substance such as a polymer. As for the type of composition and the method of application, such as spraying, spraying, dusting, scattering, coating or pouring, it is selected according to the intended target and main conditions. This ingredient may contain additional adjuvants such as stabilizers, defoamers, viscosity modifiers, binders or tackifiers, as well as other formulations such as fertilizers, micronutrient donors, etc., to achieve special effects.

Suitable carriers and adjuvants (adjuvants) may be solid or liquid, and have a role in the formulation technology, such as natural or recycled minerals, solvents, dispersants, wetting agents, tackifiers, thickeners, Adhesive or fertilizer. An example of such a vector is set forth in WO 97/33890.

The compound of the formula (I) or a composition thereof (comprising a combination of the compound of the formula (I) as an active ingredient and an inert carrier) can be applied to the planting site or the plant itself to be treated simultaneously or successively with other compounds. These other compounds may, for example, be fertilizers, micronutrient donors or other agents that affect plant growth. Other compounds may also be selective herbicides, insecticides, fungicides, fungicides, nematicides, snails if they are intended to be used in combination with other carriers, surfactants or other applications in the field of formulation. Or a mixture of the above formulations.

A preferred mode of applying a compound of formula (I) or a composition comprising a compound of formula (I) as an active ingredient and an inert carrier is applied to the leaves. The frequency and proportion of administration will depend on the risk of infection of the corresponding pathogen. However, watering the planting site in a liquid formulation, or applying a solid form of the compound to the soil, such as a granular form (soil application), allows the compound of formula (I) to penetrate the root of the plant with the soil (systemic action). In rice crops, such granules can be applied to rice fields. The compound of formula (I) can also be applied to the seed (coating) by soaking the seed or tuber with a liquid formulation fungicide or by solid formulation.

Formulations (ie, compositions comprising a compound of formula (I) and admixed with a solid or liquid adjuvant as desired) are prepared in a known manner, typically by blending agents (eg, solvents, solid carriers, and The compound can be thoroughly mixed and/or ground by using an interfacially active compound (surfactant).

In the agrochemical formulation, the compound of formula (I) usually comprises from 0.1 to 99% by weight, preferably from 0.1 to 95% by weight; solid or liquid adjuvants comprise from 99.9 to 1% by weight, of which 99.8 to 5% by weight Preferably, the surfactant comprises from 0 to 25% by weight, preferably from 0.1 to 25% by weight.

Preferably, the commercial product is formulated as a concentrate, and the end user will typically use a diluted formulation.

An advantageous application ratio is usually from 5 to 2 kg of active ingredient per hectare, wherein 10 to 1 kg of active ingredient per ha is preferably used, preferably from 20 to 600 g per application. When used as a seed drench, a suitable application ratio is from 10 mg to 1 g of active ingredient per kg of seed. The application rate of the desired effect can be confirmed experimentally. It depends on factors such as the type of utility, the stage of the actual plant development and the conditions of application (location, time and mode of administration, etc.) and, due to these parameters, may vary among the limitations.

The above compound of the formula (I) or a pharmaceutically acceptable salt thereof may also be advantageous for the treatment and/or prevention of microbial infection in animals and the like in animals. The "animal" may be any animal such as an insect, a mammal, a reptile, a fish, an amphibious, preferably a mammal, and most preferably a human. "Treatment" refers to the administration to an animal infected with a microorganism to reduce, slow or stop the aggravation or spread of the infection, or to reduce or treat the infection. "Prevention" refers to the application to an animal that does not show signs of microbial infection to prevent future infection, or to reduce or slow the progression or spread of the disease in the future.

According to the present invention, the present invention provides the use of a compound of formula (I) for the manufacture of a medicament for the treatment and/or prevention of microbial infection in an animal. The use of a compound of formula (I) as a pharmaceutical agent is also provided. The use of a compound of formula (I) as an antibacterial agent in the treatment of an animal is also provided. According to the present invention, there is also provided a pharmaceutical composition comprising the compound of the formula (I) as an active ingredient, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable diluent and carrier. The composition can be used to treat or prevent an antimicrobial infection in an animal. The pharmaceutical composition can be formulated into a form suitable for oral administration such as tablets, troches, hard capsules, aqueous suspensions, oil suspensions, emulsions, dispersible powders, dispersible granules, syrups and elixirs. Further, the pharmaceutical composition can be formulated into a form suitable for topical administration such as a spray, ointment or lotion. Further, the present pharmaceutical composition can be formulated into a form suitable for parenteral administration, such as an injection. In addition, the pharmaceutical compositions can be formulated for inhalable administration, such as aerosol sprays.

The compound of formula (I) may have an effect on the control of various microbial species which cause microbial infection in animals. Such microbial species include Aspergillus fumigatus , A. flavus , A. terrus , A. nidulans and black. A. niger ; Blastomyces dermatitidis , which causes dysbacteriosis ; Candida albicans, C. glabrata, C. tropicalis ), C. parapsilosis, C. krusei , and C. lusitaniae ; coccidioides immitis causing coccidiosis ; causing cryptococcosis Cryptococcus neoformans ; Histoplasma capsulatum causing tissue protoplasts, and Absidia corymbifera , Rhizomucor pusillus, and rootless roots causing zygomycosis Mildew ( Rizopus arrhizus ) and the like. Other examples include Fusarium Spp, such as Fusarium oxysporum and Fusarium solani , and Scedosporium Spp, such as Scedosporium. Apiospermum) and Scedosporium prolificans . Further examples include Microsporum Spp, Trichophyton Spp, Epidermophyton Spp, Mucor Spp, Sporothorix Spp, bottles Phialophora Spp, Cladosporium Spp, Petriellidium spp, Paracoccidioides Spp and Histoplasma Spp.

In addition, other biocidal active ingredients or compositions may be combined with the compounds of formula (I), employed in the methods of the invention, and administered simultaneously or sequentially with the compounds of formula (I). When applied simultaneously, these additional active ingredients can be formulated with the compound of formula (I) or incorporated into a device such as a spray can. These additional biocidal active ingredients can be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and/or plant growth regulators.

Accordingly, one aspect of the invention provides a compound of formula (I) (selected from compounds Nos. 1 to 156 of Table 1) and (1) other fungicides, (2) herbicides, (3) insecticides, 4) A composition of a bactericide, (5) acaricide, (6) nematicide, and/or (7) a plant growth regulator.

In another aspect, the invention provides a composition for use in the method of the invention, the composition comprising a compound of formula (I) (selected from compounds Nos. 1 to 156 of Table 1) and (1) other fungicides, (2) a herbicide, (3) an insecticide, (4) a bactericide, (5) an acaricide, (6) a nematicide, and/or (7) a plant growth regulator.

Furthermore, the compounds of the invention may also be administered in combination with one or more acquired whole plant resistance response elicitors ("SAR" elicitors). SAR-inducing agents are known and are described, for example, in U.S. Patent No. 6,919,298, which contains, for example, salicylates and the commercially available SAR inducer arsenic acid Benzene-S-methyl.

Furthermore, the invention relates to a mixture comprising at least a compound of formula I and at least one additional additional biocid active ingredient in combination with other ingredients. Additional examples of other known biocidal ingredients are taken from The Pesticide Manual (The Pesticide Manual-A World Compendium Handbook of Pesticides: World Abstract); 13th Edition (2003-11) New version on the 2nd of the month), editor: CDS Tomlin; The British Crop Protection Council, ISBN-10: 1901396134; ISBN-13: 978-1901396133] or its electronic version "e-Pesticide Manual V4.2" Or from the website http://www.alanwood.net/pesticides/, or preferably one of the following pesticides.

Mixtures of the following TX compounds with other active ingredients (B) are preferred (abbreviation "TX" means a compound encompassed by a compound of formula I, or "TX" preferably means a compound selected from Tables 1-39: An adjuvant selected from the group consisting of petroleum (general cross name) (628) + TX, an acaricide selected from the group consisting of the following components, the composition is 1,1-bis-(4 -Chlorophenyl)-2-ethoxyethanol (name of International Union of Pure and Applied Chemistry (IUPAC)) (910) + TX, 2,4-dichlorophenylbenzenesulfonate (IUPAC / Chemical Abstracts Name )(1059)+TX, 2-fluoro-N-methyl-N1-naphthylacetamide (IUPAC name) (1295) + TX, 4-chlorophenylphenyl hydrazine (IUPAC name) (981) + TX, avermectin (1) + TX, Aachen (3 +TX, acetamiprid [CCN]+TX, flumethrin (9)+TX, aldicarb (16)+TX, oxycarbocarb (863)+TX, alpha-cypermethrin (202)+ TX, match (870) + TX, sulfamethoxazole [CCN] + TX, guanidine thioester (872) + TX, amine phosphorus (875) + TX, acid oxalate amine phosphorus (875) + TX, Amitraz (24) + TX, chlorpyrifos (881) + TX, arsenic trioxide (882) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, ethyl azinphos (44 ) +TX, methyl azinphos (45) + TX, azobenzene (IUPAC name) (888) + TX, triazole tin (46) + TX, azo phosphorus (889) + TX, benomyl ( 62) +TX, phenoxyphosphorus (general cross name) [CCN]+TX, benzophenone (71)+TX, benzyl benzoate (IUPAC name) [CCN]+TX, Biffin (74)+TX , bifenthrin (76) + TX, lysine (907) + TX, methlicin (universal cross name) + TX, bromo (918) + TX, bromothio (920) + TX, Ethyl bromide (921) + TX, bromo oxime ester (94) + TX, chlorpyrifos (99) + TX, butanone (103) TX, butanone oxime (104) + TX, butyl Lingling (universal cross name) + TX, more Calcium (IUPAC name) (111)+TX, lanthanum chloride (941)+TX, chlorhexazone (943)+TX, carbaryl (115)+TX, carbofuran (118)+TX, three Phosphorus (947) + TX, CGA 50'439 (development code) (125) + TX, cockroach (126) + TX, chlorpyrifos (959) + TX, insecticidal 964 (964) + TX, kill Insecticide hydrochloride (964) + TX, chlorfenapyr (130) + TX, sterol (968) + TX, decyl ester (970) + TX, diazepam (971) + TX, venom (131) + TX, ethyl ester sterol (975) + TX, cockroach (977) + TX, 螟蛉 (978) + TX, propyl ester sterol (983) + TX, chlorpyrifos (145) + TX, methyl chlorpyrifos (146) + TX, chloromethyl thiophene (994) + TX, fenvalerate I (696) + TX, methyrin II (696) + TX, fenvalerate (696) + TX , tetrazine (158) + TX, cyanoguanidin (general cross name) [CCN] + TX, fly poison phosphorus (174) + TX, cromeidine (general cross name) [CCN] + TX, Butene phosphorus (1010) + TX, thiabendazole fungicide (1013) + TX, fruit worm phosphorus (1020) + TX, butafluorodecyl ester (CAS registration number: 400882-07-7) + TX, chlorofluorocyanate Pyrethroid (196)+TX, tricyclotin (199)+TX, cypermethrin (201)TX, DCPM(1032)+TX, DDT(219)+TX, Tianle phosphorus (1037)+TX, Tianle phosphorus- O(1037)+TX, Tianle Phosphorus-S(1037)+TX, Phosphorus uptake (1038)+TX, methyl endogenous phosphorus (224)+TX, endogenous phosphorus-O(1038)+TX, methyliso-phosphorus (224)+TX, and endogenous phosphorus-S(1038) +TX, Descendants (224) + TX, sputum phosphorus (1039) + TX, dibutyl ether urea (226) + TX, chloroimidate (1042) + TX, diazinon (227) + TX, Bacteriostatic (230) + TX, dichlorvos (236) + TX, dipropyl phosphine (universal cross name) + TX, dicofol (242) + TX, Baizhi phosphorus (243) + TX, dechlorinated (1071) + TX, mefphosphate (1081) + TX, dimethoate (262) + TX, bis-biotin (general cross name) (653) + TX, decylphenol (1089) + TX, Dai Nai - Dai Kexin ( 1089)+TX, enemy 螨通(269)+TX, enemy 螨普(270)+TX, enemy -4普-4[CCN]+TX, enemy -6普-6[CCN]+TX, neighboring enemy 螨1090) +TX, penemene ester (1092) + TX, nitrenate acaricide (1097) + TX, n-butyl ester (1098) + TX, dioxon (1102) + TX, diphenyl hydrazine (IUPAC name ) (1103) + TX, disulfiram (universal cross name) [CCN] + TX, bisphosphorus (278) + TX, DNOC (282) + TX, dofenapyn (1113) + TX, doramectin (general cross) Name) [CCN]+TX, endosulfan (294)+TX, toxic phosphorus (1121)+TX, EPN(297)+TX, eplenomycin (general cross name)[CCN]+TX, B Phosphorus (309) + TX, benefit Phosphorus (1134)+TX, chlorpyrifos (320)+TX, pyrithione (1142)+TX, anti-carbazole (1147)+TX, quinacridone (328)+TX, phenbutyltin (330) +TX, phenanthrene (337) + TX, fenpropathrin (342) + TX, pyridoxamine (universal cross name) + TX, oxazolidine (345) + TX, decyl ester (1157) + TX , aryl fluoride (1161) + TX, fenvalerate (349) + TX, fipronil (354) + TX, pyridoxine (360) + TX, fluzolone (1166) + TX, fluorobenzene Aminethiazole (1167) + TX, fluoroquinone urea (366) + TX, cyfluthrin (367) + TX, bisfluorene (1169) + TX, flubendiamide (370) + TX, flumethrin (372)+TX, Fluoride (1174)+TX, fluvalinate (1184)+TX, FMC 1137 (development code) (1185)+TX, worm (405)+TX, worm Hydrochloride (405)+TX, Anguo (1192)+TX, formazan (1193)+TX, lindane (430)+TX, fruit green (1205)+TX, fenfenine (424)+TX, Bismuth phosphorus (432) + TX, hexadecyl cyclopropanecarboxylate (IUPAC / Chemical Abstracts name) (1216) + TX, thiazolone (441) + TX, methyl iodide (IUPAC name) (542) + TX, acesulfame (general cross name) (473) + TX, isopropylO-(Methoxyaminothiophosphonium) salicylate (IUPAC name) (473) + TX, ivermectin (general cross name) [CCN] + TX, jasperidin I (696) + TX, Jasperate II (696) + TX, iodophos (1248) + TX, chlorinated benzene (430) + TX, guanidine urea (490) + TX, malathion (492) + TX, special Nitrile (1254)+TX, bismuth phosphorus (502)+TX, dithiaphos (1261)+TX, dimethylthiazide (general cross name)[CCN]+TX, worms (1266)+TX, A Amine phosphorus (527)+TX, chlorpyrifos (529)+TX, chlorpyrifos (530)+TX, methomyl (531)+TX, methyl bromide (537)+TX, carbendazim (550)+TX, Quick-acting phosphorus (556)+TX, self-Kewei (1290)+TX, cyclopentin (557)+TX, milbemycin oxime (general cross name) [CCN]+TX, propylamine fluoride (1293)+ TX, monocrotophos (561)+TX, Maoguo (1300)+TX, moxidectin (general cross name) [CCN]+TX, dibromophosphorus (567)+TX, NC-184 (compound code) +TX, NC-512 (compound code) + TX, nifluli (1309) + TX, nicotimycin (general cross name) [CCN] + TX, pentocyanide (1313) + TX, pentocyanide 1:1 zinc chloride complex (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, omethoate (594) + TX, kill line ( 602) +TX, isoindoline phosphorus (1324) + TX, argon phosphorus (1325) + TX, pp'-DDT (219) + TX, parathion (615) + TX, permethrin (626) + TX, petroleum oil (general cross name) (628) + TX, fenthion (1330) + TX, rice flour (631) + TX, phorate (636) + TX, voltamate (637) + TX , cotton anion (1338) + TX, imipenem (638) + TX, phosphorus amine (639) + TX, phoxim (642) + TX, methyl pyrimidine (652) + TX, polychlorinated Alkene (traditional name) (1347) + TX, polynamin (general cross name) (653) + TX, chlorohydrin (1350) + TX, profenofos (662) + TX, Converse (1354) )+TX, Ketite (671)+TX, methionem (673)+TX, propoxur (678)+TX, ethiazole (1360)+TX, fruit (1362)+TX, pyrethrum Ester I (696) + TX, pyrethrin II (696) + TX, pyrethrin (696) + TX, 哒螨 ( (699) + TX, pyridazin (701) + TX, Fen (706)+TX, pyrimidine phosphorus (1370)+TX, quetiaphos (711)+TX, quetiaphos (1381)+TX, R-1492 (development code) (1382)+TX, RA-17 ( Development code) (1383) + TX, rotenone (722) + TX, octaphosphorus (1389) + TX, sulphur phosphorus (general cross name) + TX, sectin (general cross name) [CCN] + TX, SI-0009 (compound code) + TX, Suguo (1 402) +TX, spiro-ester (738) + TX, spironolactone (739) + TX, SSI-121 (development code) (1404) + TX, Shufeilun (universal cross name) [CCN] + TX Sulfluramid (750)+TX, guanidine phosphorus (753)+TX, sulfur (754)+TX, SZI-121 (development code) (757)+TX, fluvalinate (398)+TX, Pyridoxamine (763) + TX, TEPP (1417) + TX, tert-butyl (general cross name) + TX, insecticidal (777) + TX, tetrachloro acaricidal (786) + TX, four antibiotics ( Universal cross name) (653)+TX, killing good (1425)+TX, thiophene (general cross name)+TX, insecticide (1431)+TX, Jiuweiwei (800)+TX, methyl Acetate (801) + TX, gram (1436) + TX, sulindac (general cross name) [CCN] + TX, triazophos (1441) + TX, benzoquinone (1443) + TX, triazophos (820) + TX, oxazide (general cross name) + TX, trichlorfon (824) + TX, phosphorus oxychloride (1455) + TX, trisporin (general cross name) (653)+TX, annihilation (847)+TX, fenidazole [CCN], and YiI-5302 (compound code)+TX, an algicide, are selected from the group consisting of the following components, The composition is benzoxazine [CCN]+TX, copper dioctoate (IUPAC name) (170)+TX, copper sulfate (172)+TX, and thiophene Triazine [CCN]+TX, dichloronaphthylquinone (1052)+TX, dihydroxydichlorodiphenylmethane (232)+TX, cadmium (295)+TX, triphenyltin (347)+TX, slaked lime [CCN]+TX, Desson sodium (566)+TX, Mokgrass (714)+TX, indigoamine (1379)+TX, simazine (730)+TX, triphenylacetate (IUPAC name (347) and triphenyltin hydroxide (IUPAC name) (347) + TX, an anthelmintic, selected from the group consisting of avermectin (1) + TX , breeding livestock phosphorus (1011) + TX, doramectin (universal cross name) [CCN] + TX, emamectin (291) + TX, a vitamin salt (291) + TX, Eplino Phytocin (general cross name) [CCN]+TX, ivermectin (general cross name) [CCN]+TX, milbemycin oxime (general cross name) [CCN]+TX, morocin ( Universal cross name) [CCN] + TX, piperazine [CCN] + TX, slakeddin (general cross name) [CCN] + TX, spinosyn (737) and methyl thiophanate (1435) + TX, a kind The bird killing agent is selected from the group consisting of chloralose (127)+TX, endrin (1122)+TX, fenthion (346)+TX, and pyridine-4. -amine (IUPAC name) (23) and horse money Base (745) + TX, a fungicide, is selected from the group consisting of 1-hydroxy-1 hydrogen-pyridine-2-thione (IUPAC name) (1222) + TX, 4 -(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748)+TX, 8-hydroxyquinoline sulfate (446)+TX, bronopol (97)+TX, copper dioctoate (IUPAC name) (170) + TX, copper hydroxide (IUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophene (232) + TX, dithiopyridin (1105) + TX, Du Dixin (1112)+TX, Dixon (1144)+TX, Formaldehyde (404)+TX, Mercury Plus (General Cross Name) [CCN]+TX, Chunleimycin (483)+TX, Spring Raper Hydrochloride salt hydrate (483) + TX, bis (dimethyl dithiocarbamate) nickel (IUPAC name) (1308) + TX, nitropyridine (580) + TX, octyl isothiophenone (590) +TX, oxolinic acid (606)+TX, oxytetracycline (611)+TX, hydroxyquinoline potassium sulfate (446)+TX, thiabendazole (658)+TX, streptomycin (744)+TX, Streptomycin sulfate (744) + TX, gram rot (766) + TX and thimerosal (general cross name) [CCN] + TX, a biological preparation, selected from the group consisting of the following components, ingredients Cotton brown moth (Adoxophyes orana GV) (Universal Cross Name) (12) + TX, Agrobacterium radiotypes (Agrobacterium radiobacter)(Universal cross name) (13) + TX, blunt species (Amblyseius Spp.) (Universal Cross Name) (19) + TX, Celery Noctuidae (Anagrapha falcifera NPV) (Universal cross name) (28) + TX, 缨 缨 缨Anagrus atomus) (Universal cross name) (29) + TX, 苜蓿蚜 small bee (Aphelinus abdominalis) (Universal Cross Name) (33) + TX, 蚜 Coleman (Aphidius colemani) (Universal cross name) (34) + TX, 蚜瘿 mosquito (Aphidoletes aphidimyza) (Universal Cross Name) (35) + TX, Spodoptera frugiperda (Autographa californica NPV) (Universal Cross Name) (38) + TX, Bacillus licheniformis (Bacillus firmus) (Universal cross name) (48) + TX, Bacillus sphaericus (Bacillus sphaericus Neide) (scientific name) (49) + TX, Bacillus thuringiensis (Bacillus thuringiensis Berliner) (scientific name) (51) + TX, Su Li bacteriaBacillus thuringiensis subsp. aizawai) (scientific name) (51) + TX, Bacillus thuringiensis subspecies of Israel (Bacillus thuringiensis subsp. israelensis) (scientific name) (51) + TX, Bacillus thuringiensis subsp.Bacillus thuringiensis subsp. japonensis) (scientific name) (51) + TX, Bacillus thuringiensis kurstaki subspecies (Bacillus thuringiensis subsp. kurstaki) (scientific name) (51) + TX, Bacillus thuringiensis tenebrionis subspecies (Bacillus thuringiensis subsp. tenebrionis) (scientific name) (51) + TX, Beauveria bassiana (Beauveria bassiana) (Universal cross name) (53) + TX, Beauveria bassiana (Beauveria brongniartii) (Universal cross name) (54) + TX, ordinary grasshopper (Chrysoperla carnea) (Universal cross name) (151) + TX, Monteggia sinensis (Cryptolaemus montrouzieri) (Universal cross name) (178) + TX, apple stupid moth granulosis virus (Cydia pomonella GV) (Universal Cross Name) (191) + TX, Siberian 颚茧 bee (Dacnusa sibirica) (Universal cross name) (212) + TX, peasDiglyphus isaea) (Universal Cross Name) (254) + TX, Radisson Blu Bee (Encarsia formosa) (scientific name) (293) + TX, scorpion horned bee (Eretmocerus eremicus) (Universal cross name) (300) + TX, American cotton bollworm (Helicoverpa zea NPV) (Universal Cross Name) (431) + TX, HeteroderaHeterorhabditis bacteriophora)versusH. megidis(Universal cross name) (433) + TX, poly-legged ladybug (Hippodamia convergens) (Universal cross name) (442) + TX, parasitic tangerine powder scale insects (Leptomastix Dactylopii)(Universal cross name) (488) + TX, predatory artifacts (Macrolophus caliginosus)(Universal cross name) (491) + TX, cabbage blue moth (Mamestra brassicae NPV) (Universal Cross Name) (494) + TX, Metaphycus helvolus (Universal Cross Name) (522) + TX, Metarhizium anisopliae (Metarhizium anisopliae var. acridum)(scientific name) (523) + TX, Metarhizium (Metarhizium anisopliae var. anisopliae) (scientific name) (523) + TX, European pine rust sawdust bee (Neodiprion sertifer NPV) and red-headed pine bee (N. lecontei NPV) (Universal Cross Name) (575) + TX, Small Flower 蝽 (Orius spp.) (Universal Cross Name) (596) + TX, Paecilomyces variabilis (Paecilomyces fumosoroseus) (Universal Cross Name) (613) + TX, Chilean Plantation (Phytoseiulus persimilis) (Universal Cross Name) (644) + TX,Spodoptera exigua multicapsid nuclear polyhedrosis virus(scientific name) (741) + TX,Steinernema bibionis(Universal Cross Name) (742) + TX, M. elegans (Steinernema carpocapsae) (Universal Cross Name) (742) + TX, Spodoptera frugiperda (Steinernema feltiae) (Universal Cross Name) (742) + TX,Steinernema glaseri(Universal Cross Name) (742) + TX,Steinernema riobrave(Universal Cross Name) (742) + TX,Steinernema riobravis(Universal Cross Name) (742) + TX, M. elegans (Steinernema scapterisci) (Universal Cross Name) (742) + TX, Streptomyces elegans (Steinernema spp.) (Universal Cross Name) (742) + TX, Trichogramma (Trichogramma spp.) (Universal Cross Name) (826) + TX, Western blind walk (Typhlodromus occidentalis)(Universal Cross Name) (844) and Verticillium lecanii (Verticillium lecanii(General Cross Name) (848) + TX, a soil sterilant, selected from the group consisting of methyl iodide (IUPAC name) (542) and methyl bromide (537) + TX, a kind The chemical sterilizing agent is selected from the group consisting of oxazolazine [CCN]+TX, bisazir (general cross name) [CCN]+TX, busulfan (general cross name) [CCN ]+TX, chlorfenapyr (250)+TX, dimatif (general cross name) [CCN]+TX, hexamethylene amide [CCN]+TX, hexamethylphosphorus [CCN]+TX, methyl hydrazine [CCN]+ TX, methylthiocarbamate [CCN]+TX, methyl sterile (CCN)+TX, morzid[CCN]+TX, fluorojumolone (general cross name)[CCN]+TX, 涕巴[CCN]+ TX, thiohempa (general cross name) [CCN] + TX, thiotepa (general cross name) [CCN] + TX, infertility (general cross name) [CCN] and urethane imine (general cross name) [ CCN]+TX, an insect pheromone, is selected from the group consisting of the following components.E)-癸-5-en-1-olE)-indole-5-en-1-ate (IUPAC name) (222) + TX, acetic acid (E)-tridec-4-en-1-ester (IUPAC name) (829) + TX, (E)-6-methylhept-2-en-4-ol (IUPAC name) (541) + TX, (E, Z)-tetradecane-4,10-diene-1-acetate (IUPAC name) (779) + TX, acetic acid (Z)-Dodec-7-en-1-ester (IUPAC name) (285) + TX, (Z)-hexadecyl-11-enal (IUPAC name) (436) + TX, acetic acid (Z)-hexadec-11-en-1-actyl (IUPAC name) (437) + TX, acetic acid (Z)-hexadeca-13-ene-11-alkyn-1-ester (IUPAC name) (438)+TX, (Z)-Tetra-13-en-1-one (IUPAC name) (448) + TX, (Z)-tetradec-7-en-1-yl (IUPAC name) (782) + TX, (Z)-tetradec-9-en-1-ol (IUPAC name) (783) + TX, (Z)-tetradec-9-ene-1-acetate (IUPAC name) (784) + TX, Acetic acid (7E,9Z)-Twelve-7,9-dien-1-ester (IUPAC name) (283)+TX, (9Z,11E)-tetradecane-9,11-diene-1-acetate (IUPAC name) (780)+TX, acetic acid (9Z, 12E)-tetradec-9,12-dien-1-ester (IUPAC name) (781) + TX, 14-methyl octadec-1-ene (IUPAC name) (545) + TX, containing 4-A 4-methylindole-5-ol based on 5-ketone (IUPAC name) (544) + TX, α-polymorph (general cross name) [CCN] + TX, brevicomin (general cross name) [CCN ]+TX, codlelure (general cross name) [CCN]+TX, dodecadienol (general cross name) (167)+TX, melon fly attractant (general cross name) (179)+TX, Female Gypsy moth attractant (277) + TX, dodecane-8-en-1-yl acetate (IUPAC name) (286) + TX, dodecane-9-en-1-yl acetate ( IUPAC name) (287) + TX, dodecane-8 + TX, 10-dien-1-yl acetate (IUPAC name) (284) + TX, Stupid attractant No. 2 (general cross name) [ CCN]+TX, ethyl 4-octanoate (IUPAC name) (317)+TX, eugenol (general cross name) [CCN]+TX, southern pine scorpion attractant (general cross name) [CCN] +TX, cotton bollworm sex attractant (general cross name) (420) + TX, decoy olefin mixture (421) + TX, decoy olefin mixture I (universal cross name) (421) + TX, trapping olefin Agent II (general cross name) (421) + TX, decoy olefin mixture III (universal cross name) (421) + TX, Decoy olefin mixed IV (general cross name) (421) + TX, red bell condensate [CCN] + TX, dentate decadienol (universal cross name) [CCN] + TX, dentate decyl alcohol (general Cross name) [CCN]+TX, chafer attractant (general cross name) (481)+TX, trimethyldioxytricyclodecane (general cross name) [CCN]+TX, night moth attractant (generic Cross name) [CCN]+TX, lure moth ester (general cross name) [CCN]+TX, decoy ester [CCN]+TX, tetradecadienoic acid (general cross name) [CCN]+TX, insect Ether (Universal Cross Name) (540) + TX, Musca domestica attractant (563) + TX, octadecyl-2,13-diene-1-acetate (IUPAC name) (588) + TX, 18 Carbon-3,13-diene-1-acetate (IUPAC name) (589)+TX, Ovra Road (general cross name) [CCN]+TX, Oritas Road (general cross name) (317 ) +TX, tetradecenyl acetate (universal cross name) [CCN] + TX, Mediterranean fruit fly attractant [CCN] + TX, sodidine (general cross name) (736) + TX, bacterium A Alcohol (general cross name) [CCN]+TX, tetradecyl-11-ene-1-acetate (IUPAC name) (785)+TX, Mediterranean fruit fly attractant (839)+TX, Mediterranean Fly attractant A (general cross name) (839 )+TX, Mediterranean fruit fly attractant B₁(Universal cross name) (839) + TX, Mediterranean fruit fly attractant B₂(Universal cross name) (839) + TX, Mediterranean fruit fly attractant C (general cross name) (839) and Chuangke (general cross name) [CCN] + TX, an insect repellent, is from Selected from the group consisting of 2-(octylsulfo)-ethanol (IUPAC name) (591)+TX, butyltrimethyllated oxygen (933)+TX, butoxy (polypropylene glycol) (936) + TX, dibutyl adipate (IUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (IUPAC name) (1048) + TX , diethyl toluidine amine [CCN] + TX, mosquito repellent [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1137) + TX, diethylamine Phenobarbital [CCN] + TX, quinoline carboxylate (1276) + TX, methyl neodecylamine [CCN] + TX, oxamate salt [CCN] and picarein [CCN] + TX, An insecticide selected from the group consisting of 1-dichloro-1-nitroethane (IUPAC/Chemical Abstracts Name) (1058) + TX, 1,1-dichloro -2,2-bis(4-ethylphenyl)ethane (IUPAC name) (1056) + TX, 1,2-dichloropropane (IUPAC / Chemical Abstracts Name) (1062) + TX, 1, 2- Chloropropane and 1,3-dichloropropene (IUPAC name) (1063) + TX , 1-bromo-2-chloroethane (IUPAC/Chemical Abstracts Name) (916) + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)acetate (IUPAC name (1451)+TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl phosphate (IUPAC name) (1066) + TX, 2-(1,3-dithiocyclopentane Dimethyl 2-phenyl)phenylaminecarboxylate (IUPAC/Chemical Abstracts Name) (1109)+TX, 2-(2-butoxyethoxy)ethylthiocyanate (IUPAC/Chemical Abstract) (935)+TX, methyl 2-(4,5-dimethyl-1,3-dioxocyclopentan-2-ylphenylaminecarboxylate (IUPAC/Chemical Abstracts Name) (1084)+TX, 2 -(4-chloro-3,5-xylyleneoxy)ethanol (IUPAC name) (986) + TX, 2-chloroethylene diethyl phosphate (IUPAC name) (984) + TX, 2-imidazolidinone ( IUPAC name) (1225) + TX, 2-isoamylindenidine-1,3-dione (IUPAC name) (1246) + TX, 2-methyl (prop-2-ynyl) aminobenzene Methyl carbazide (IUPAC name) (1284) + TX, 2-thiocyanoethyl laurate (IUPAC name) (1433) + TX, 3-bromo-1-chloro-1-propene (IUPAC name) ( 917) +TX, 3-methyl-1-phenylpyrazole-5-dimethyl dimethylcarbamate (IUPAC name) (1283) + TX, 4-methyl (prop-2-ynyl) ammonia-3 , methyl 5-dimethylphenylcarbamate (IUPAC name )(1285)+TX, dimethylaminocarbamic acid 5,5-dimethyl-3-oxocyclohex-1-ene ester (IUPAC name) (1085)+TX, avermectin (1)+TX , methotrexate (2) + TX, acetamiprid (4) + TX, housefly phosphorus (general cross name) [CCN] + TX, acetaminophen [CCN] + TX, flumethrin ( 9) +TX, acrylonitrile (IUPAC name) (861) + TX, cotton ring (15) + TX, aldicarb (16) + TX, oxygen aldicarb (863) + TX, Aldrin (864) +TX, methrin (17) + TX, alemsin (general cross name) [CCN] + TX, chlorpyrifos (866) + TX, alpha cypermethrin (202) + TX, α-skin Hormone (general cross name) [CCN] + TX, aluminum phosphide (640) + TX, match (870) + TX, thiourethane (872) + TX, chlorpyrifos (873) + TX, amine absorption Phosphorus (875)+TX, acid oxalate amine phosphorus (875)+TX, amitraz (24)+TX, neonicotinine (877)+TX, ethyl chlorpyrifos (883)+TX, AVI 382 ( Compound code) +TX, AZ 60541 (compound code) + TX, azadirachtin (universal cross name) (41) + TX, pyridinium (42) + TX, ethyl azinphos (44) + TX, Methyl azinphos (45) + TX, azo phosphorus (889) + TX, Bacillus thuringiensis (Bacillus thuringiensisΔ-endotoxin (general cross name) (52)+TX, bismuth hexafluoroantimonate (general cross name) [CCN]+TX, bismuth polysulfide (IUPAC/Chemical Abstracts) (892)+TX, pepper Pyrethrum [CCN]+TX, Bayer 22/190 (development code) (893)+TX, Bayer 22408 (development code) (894)+TX, Insecticide (58)+TX, and thiocarbamate 60) +TX, insecticidal sulfonate (66) + TX, beta-cyfluthrin (194) + TX, beta-cypermethrin (203) + TX, bifenthrin (76) + TX, bio-methrin (78) +TX, valproateS- cyclopentenyl isomer (general cross name) (79) + TX, bioethanomethrin [CCN] + TX, permethrin (908) + TX, bio-impura (80) + TX, double (2- Chloroethyl)ether (IUPAC name) (909)+TX, ditriazole urea (83)+TX, borax (86)+TX, methrin (general cross name)+TX, methylbromophene Phosphorus (914)+TX, bromobenzene (918)+TX, bromine drip (general cross name) [CCN]+TX, bromothion (920)+TX, ethyl bromide (921)+TX, butyl Benzyl ester (924) + TX, chlorpyrifos (99) + TX, butyl methacrylate (926) + TX, demethyl propyl pyrimidine phosphine (927) + TX, butanone (103) + TX, Butyl phosphate (932)+TX, butanone oxime (104)+TX, butyl dadolin (general cross name)+TX, sulphur phosphorus (109)+TX, calcium arsenate [CCN]+TX, Calcium cyanide (444)+TX, calcium polysulfide (IUPAC name) (111)+TX, toxaphene (941)+TX, chlorhexazone (943)+TX, carbaryl (115)+TX, gram Budweiser (118)+TX, carbon disulfide (IUPAC/Chemical Abstracts) (945)+TX, carbon tetrachloride (IUPAC name) (946)+TX, trisulfide (947)+TX, butyl thiocarbacarb (119)+TX, chlorpyrifos (123)+TX, chlorpyrifos hydrochloride (123)+TX, sivadine (general cross name) (725)+TX, borneol (960)+TX, chlordane (128)+TX, chlordecone (963)+TX, chlorpyrifos (964)+TX, chlorpyrifos hydrochloride (964)+TX, chlorophosphonate (129) +TX, chlorfenapyr (130)+TX, chlorpyrifos (131)+TX, chlorfenapyr (132)+TX, chloromethylphosphonate (136)+TX, chloroform [CCN]+TX, trichloronitro Methane (141) + TX, chloronitrile phosphine (989) + TX, chlorpyrifos (990) + TX, chlorpyrifos (145) + TX, methyl chlorpyrifos (146) + TX, chloromethion (994) + TX, ringworm mites (150) + TX, fenvalerate I (696) + TX, methyrin II (696) + TX, guavarin (696) + TX, cis-resmethrin (general cross name) +TX, cismethrin (80) + TX, cyhalothrin (general cross name) + TX, in addition to line (999) + TX, cyanoguanidin (general cross name) [CCN] + TX, clothianidin ( 165)+TX, acetonitrile copper arsenate [CCN]+TX, copper arsenate [CCN]+TX, copper oleate [CCN]+TX, fly poisonous phosphorus (174)+TX, livestock phosphorus (1006) +TX, Cromitone (general cross name) [CCN]+TX, butene phosphorus (1010)+TX, breeding phosphorus (1011)+TX, cryolite (general cross name) (177)+TX, CS 708 (development code) (1012) + TX, benzonitrile phosphorus (1019) + TX, acaricidal nitrile (184) + TX, fruit insect phosphorus (1020) + TX, ringworm chrysanthemum [CCN] + TX, fentanyl Ester (188)+TX Cyfluthrin (193) + TX, cyhalothrin (196) + TX, cypermethrin (201) + TX, cyprofen (206) + TX, cytosine (209) + TX, racemic phosphorus ( Universal cross name) [CCN]+TX, celery (general cross name) [CCN]+TX, dextromethrin (general cross name) (788)+TX, DAEP(1031)+TX, tampon ( 216)+TX, DDT(219)+TX, Jiabaofu (1034)+TX, deltamethrin (223)+TX, Tianle Phosphorus (1037)+TX, Tianle Phosphorus-O(1037)+TX , Tianle Phosphorus-S(1037)+TX, inhaled phosphorus (1038)+TX, methyl endophos (224)+TX, endogenous phosphorus-O(1038)+TX, methylisophosphorus ( 224) +TX, Descendants (1038) + TX, endogenous phosphorus-S-methyl (224) + TX, sputum phosphorus (1039) + TX, dibutyl ether urea (226) + TX, chloroimine sulfur Phosphorus (1042)+TX, diamine phosphorus (1044)+TX, diazinon (227)+TX, isothiaphos (1050)+TX, dephosphorization (1051)+TX, dichlorvos (236)+TX , 2 g of phosphine (general cross name) + TX, dicresyl (general cross name) [CCN] + TX, Baizhi phosphorus (243) + TX, cyclosporin (244) + TX, dieldrin (1070) + TX , 5-methylpyrazol-3-yl phosphate diethyl ester (IUPAC name) (1076) + TX, chlorfenapyr (250) + TX, hydroxypropyl theophylline (general cross name) [CCN] + TX, Tetrafluorocarbon Ethyl cholate [CCN] + TX, mefphosphate (1081) + TX, dime (1085) + TX, dimethoate (262) + TX, fenthrin (1083) + TX, methyl chlorpyrifos ( 265)+TX, Diptera (1086)+TX, decylphenol (1089)+TX, Daina-Dikexin (1089)+TX, nitrophenol (1093)+TX, pentophenol (1094) +TX, dinose (1095)+TX, dinotefuran (271)+TX, phenidrin (1099)+TX, fruit and vegetable phosphorus (1100)+TX, dioxin (1101)+TX, dioxon (1102) + TX, bisphosphorus (278) + TX, dexyl phosphine (1108) + TX, DNOC (282) + TX, Doramectin (general cross name) [CCN] + TX, DSP (1115) +TX, ecdysterone (general cross name) [CCN] + TX, EI 1642 (development code) (1118) + TX, avidin (291) + TX, emamectin benzoate ( 291) +TX, EMPC (1120) + TX, dextromethrin (292) + TX, endosulfan (294) + TX, toxic phosphorus (1121) + TX, endrin (1122) + TX , EPBP (1123) + TX, EPN (297) + TX, juvenile ether (1124) + TX, Eplino (general cross name) [CCN] + TX, S-fenvalerate (302) + TX , Etataphosphine (Universal Cross Name) [CCN]+TX, Insecticidal (308)+TX, Ethionine (309)+TX, Ethyl Nitrile (310)+TX, Dithizone (1134)+TX , propyl phosphate (312) + TX, ethyl formate (IUP AC name) [CCN] + TX, ethyl - DDD (universal cross name) (1056) + TX, dibromoethylene (316) + TX, dichloroethylene (chemical name) (1136) + TX, ethylene oxide [CCN]+TX, etofenproxate (319)+TX, pyrithione (1142)+TX, EXD(1143)+TX, sulfaphos (323)+TX, benzenephosphorus (326)+TX, Anti-carbazole (1147)+TX, picophos (1148)+TX, diethylphenol methylcarbamate (1149)+TX, fenfluramine (1150)+TX, fenthion (335)+TX, Zhongdingwei (336)+TX, fenofol (1153)+TX, phenoxycarb (340)+TX, pyrethyrazine (1155)+TX, fenpropathrin (342)+ TX, pyridoxamine (general cross name) + TX, Fonsophos (1158) + TX, fenthion (346) + TX, ethyl fenthion [CCN] + TX, fenvalerate (349) + TX, fipronil (354) + TX, fluramide (358) + TX, flubendiamide (CAS. Registration number: 272451-65-7) + TX, flucofuron (1168) + TX, fluoroquinone Urea (366)+TX, cyfluthrin (367)+TX, bifluorinated iridium (1169)+TX, acetamiprid[CCN]+TX, flubendiamide (370)+TX, trifluthrin ( 1171) +TX, flumethrin (372) + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, fonofos (1191) + TX, worm ( 405) +TX, cutting Bismuth hydrochloride (405) + TX, Anguo (1192) + TX, formparanate (1193) + TX, fensulfuron (1194) + TX, formazin (1195) + TX, thiazolyl (408) + TX, cut line Dan (1196) + TX, furosemide (412) + TX, furfural (1200) + TX, super efficient cyhalothrin (197) + TX, lindane (430) + TX, guazatine (422 ) +TX, biguanide acetate (422) + TX, GY-81 (development code) (423) + TX, fenfenine (424) + TX, chlorfenapyr (425) + TX, HCH (430) +TX, HEOD(1070)+TX, heptachlor (1211)+TX, bismuth phosphorus (432)+TX, chlorpyrifos [CCN]+TX, hexaflumuron (439)+TX, HHDN (864) +TX, fluoroantimony (443)+TX, hydrogen cyanide (444)+TX, methionil ethyl ester (445)+TX, hyquincarb(1223)+TX, imidacloprid (458)+TX, methadin ( 460) +TX, indoxacarb (465) + TX, methyl iodide (IUPAC name) (542) + TX, IPSP (1229) + TX, chlorazol (1231) + TX, carbochlor (1232) + TX , Isocarbophos (general cross name) (473) + TX, isopic acid (1235) + TX, iso-phosphorus (1236) + TX, isolan (1237) + TX, isopropyl (472) + TX ,O-(Methoxy-aminothiophosphoric acid) isopropyl salicylate (IUPAC name) (473) + TX, indole (474) + TX, isopropyl phosphate (1244) + TX, oxazolyl (480 ) +TX, ivermectin (general cross name) [CCN] + TX, jasmine I (696) + TX, jasperate II (696) + TX, iodophos (1248) + TX, child care Hormone I (general cross name) [CCN] + TX, juvenile hormone II (general cross name) [CCN] + TX, juvenile hormone III (general cross name) [CCN] + TX, Kelafan (1249) + TX, pronuclear (484) + TX, lambda-cyhalothrin (198) + TX, lead arsenate [CCN] + TX, lepimectin (CCN) + TX, p-bromo-phosphorus (1250) + TX, Chlorinated benzene (430) + TX, lirimfos (1251) + TX, guanidine urea (490) + TX, thiazolyl (1253) + TX,mMethyl cumyl carbamate (IUPAC name) (1014) + TX, magnesium phosphide (IUPAC name) (640) + TX, malathion (492) + TX, special nitrile (1254) + TX, Azido phosphorus (1255)+TX, bismuth phosphorus (502)+TX, methyl quinone phosphorus (1258)+TX, chlorpyrifos (1260)+TX, dithiaphos (1261)+TX, chloride Mercury (513) + TX, mesulfenfos (1263) + TX, cyanofluorfen (CCN) + TX, Weibaimu (519) + TX, metam-potassium (universal cross name) (519) + TX, Wei is mu (519)+TX, worm (1266)+TX, methamidophos (527)+TX, sulfonium fluorofluoride (IUPAC/Chemical Abstracts) (1268)+TX, chlorpyrifos (529)+TX, "Insecta" (530) + TX, insecticidal ethylene phosphorus (1273) + TX, methomyl (531) + TX, methoprene (532) + TX, quinoline carboxylate (1276) + TX, pyrethrin (Universal cross name) (533) + TX, methoxychlor (534) + TX, methoxy worm (535) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, Trichloroethane (general cross name) [CCN]+TX, dichloromethane [CCN]+TX, trimethoprim [CCN]+TX, carbaryl (550)+TX, oxaloin (1288) ) +TX, fast-acting phosphorus (556) + TX, self-Kewei (1290) + TX, metostatin (557) + TX, milbemycin oxime (general cross name) [CCN ] +TX, propylamine fluoride (1293) + TX, mirex (1294) + TX, monocrotophos (561) + TX, Mao fruit (1300) + TX, moxidectin (general cross name) [CCN] +TX, naphthoquinone phosphorus (general cross name) [CCN]+TX, dibromophosphorus (567)+TX, naphthalene (IUPAC/Chemical Abstracts) (1303)+TX, NC-170 (development code) (1306) +TX, NC-184 (compound code) + TX, nicotine (578) + TX, nicotine sulfate (578) + TX, nifluli (1309) + TX, nitenpyram (579) + TX, thia Oxazine (1311)+TX, pentamidine (1313)+TX, pentamecazine 1:1 zinc chloride complex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250 (compound code +TX, nornicotine (traditional name) (1319) + TX, diphenylfluorourea (585) + TX, polyfluorourea (586) + TX, ethyl thiophosphoric acid -O-5-dichloro-4-iodophenyl-O- Ethyl ester (IUPAC name) (1057) + TX, thiophosphoric acidO,O-diethylO-4-methyl-2-oxo-2H-benzopiperan-7-ester (IUPAC name) (1074) + TX, thiophosphoric acidO,O-diethylO-6-methyl-2-propylpyrimidine-4-ester (IUPAC name) (1075) + TX,O,O,O',O'-tetrapropyl dithio pyrophosphate (IUPAC name) (1424) + TX, oleic acid (IUPAC name) (593) + TX, omethoate (594) + TX, kill line (602) + TX , yttrium phosphorus (609)+TX, isoindoline phosphorus (1324)+TX, bismuth phosphorus (1325)+TX, pp'-DDT(219)+TX, p-dichlorobenzene[CCN]+TX, pair Phosphorus (615)+TX, methyl parathion (616)+TX, fluorojumol (General Cross Name) [CCN]+TX, pentachlorophenol (623)+TX, pentachlorophenyl laurate (IUPAC) Name) (623) + TX, permethrin (626) + TX, petroleum oil (general cross name) (628) + TX, PH60-38 (development code) (1328) + TX, fenthion (1330) + TX, phenethrin (630)+TX, Daofengsan (631)+TX, phorate (636)+TX, phosgene (637)+TX, cotton anion (1338)+TX, imine Phosphorus (638)+TX, p-chlorophosphonium (1339)+TX, phosphonium (639)+TX, phosphine (IUPAC name) (640)+TX, phoxim (642)+TX, methyl Phoxim (1340)+TX, pirimetaphos (1344)+TX, anti-River (651)+TX, ethylpyrimidine (1345)+TX, methylpyrimidine (652)+TX, polychlorinated dicyclopentane Diene isomer (IUPAC name) (1346) + TX, polychlorinated (traditional name) (1347) + TX, potassium arsenite [CCN] + TX, potassium thiocyanate [CCN] + TX, alkyne Permethrin (655) + TX, precocious I (general cross name) [CCN] + TX, precocious hormone II (general cross name) [CCN] + TX, precocious hormone III (general cross name) [CCN] + TX, primidophos ( 1349)+TX, profenofos (662)+TX, fipronil [CCN]+TX, Converse (1354)+TX, chlorpyrifos (1355)+TX, propylidene (1356)+TX , methionem (673) + TX, propoxur (678) + TX, ethiazole (1360) + TX, propionate (686) + TX, hair (1362) + TX, protrifenbute [CCN] + TX , pymetrozine (688) + TX, pyrazophos (689) + TX, fixed phosphorus (693) + TX, pyresmethrin (1367) + TX, pyrethrin I (696) + TX, pyrethrum Ester II (696) + TX, pyrethrin (696) + TX, 哒螨 ( (699) + TX, trifluoromethyl pyrithion (700) + TX, pyridazin (701) + TX, Fen (706)+TX, pyrimidine phosphorus (1370)+TX, pyriproxyfen (708)+TX, bitter wood plant (general cross name) [CCN]+TX, quetiapine (711)+TX, quetiapine Phosphorus-methyl (1376)+TX, quinothion (1380)+TX, quetiapine (1381)+TX, R-1492 (development code) (1382)+TX, Rafanet (general cross name) [CCN ] +TX, fenfenyl (719) + TX, rotenone (722) + TX, RU 15525 (development code) (723) + TX, RU 25475 (development code) (1386) + TX, fish Ding (Universal Cross Name) (1387) + TX, Liannod (traditional name) (1387) + TX, Sabah Gourd (Universal Cross Name) (725) + TX, Octaphos (1389) + TX, sulfur Line Phosphorus (Universal Cross Name) + TX, Sracectin (Universal Cross Name) [CCN] + TX, SI-0009 (Compound Code) + TX, SI-0205 (Compound Code) + TX, SI-0404 (Compound Code ) +TX, SI-0405 (compound code) + TX, flumethrin (728) + TX, SN 72129 (development code) (1397) + TX, sodium arsenite [CCN] + TX, sodium cyanide ( 444) + TX, sodium fluoride (IUPAC / Chemical Abstracts name) (1399) + TX, sodium hexafluoroantimonate (1400) + TX, sodium pentachlorophenol (623) + TX, sodium selenate (IUPAC name) (1401)+TX, sodium thiocyanate [CCN]+TX, sucrose (1402)+TX, spinosyn (737)+TX, snail (739)+TX, spirotetramat (CCN) +TX, sulcofuron (746) + TX, sulcofuron-sodium (746) + TX, flubendiamide (750) + TX, bismuth phosphorus (753) + TX, thiopurine fluoride (756) + TX, thiophanate (1408) + TX, tar (general cross name) (758) + TX, fluvalinate (398) + TX, thiazide (1412) + TX, TDE (1414) + TX, insect worm (762 +TX, pyridoxamine (763) + TX, butyl pyrimidine (764) + TX, worm (768) + TX, tefluthrin (769) + TX, thiomethylbisphosphonate (770)+TX, TEPP(1417)+TX, cyclopentenyl (1418)+TX, tert-butyl (general cross name)+TX, tert-butyl (773)+TX Tetrachloroethane [CCN]+TX, insecticidal (777)+TX, methrin (787)+TX, high-efficiency transcypermethrin (204)+TX, thiacloprid (791)+TX, thiafenox ( Universal cross name) +TX, thiamethoxam (792) + TX, thicrofos (1428) + TX, insect resistance (1431) + TX, insecticidal ring (798) + TX, thiophane (798) + TX, Sulfur dithiocarb (799) + TX, Jiuwei (800) + TX, methyl phosphine (801) + TX, thiophosphazene (1434) + TX, thiosultap (803) + TX, thiosultap-sodium (803 +TX, sulindac (general cross name) [CCN] + TX, oxazolamide (809) + TX, tetrabromopyr (812) + TX, tetrafluthrin (813) + TX, Transpermethrin (1440) + TX, triazophos (1441) + TX, oxazolidine (818) + TX, triazophos (820) + TX, oxazide (general cross name) + TX, trichlorfon ( 824) +TX, trichlormetaphos-3 (universal cross name) [CCN] + TX, soil phosphorus (1452) + TX, phosphorus oxychloride (1455) + TX, triflumuron (835) + TX, mixed kill Wei (840)+TX, methionil (1459)+TX, annihilation (847)+TX, vaniliprole[CCN]+TX, cucurbitine (general Cross name) (725) + TX, cucurbitine (general cross name) (725) + TX, XMC (853) + TX, chlorpyrifos (854) + TX, YI-5302 (compound code) + TX, Cypermethrin (205) + TX, zetamethrin (universal cross name) + TX, zinc phosphide (640) + TX, zolaprofos (1469) and ZXI8901 (development code) (858) + TX, cyanamide [736994-63- 19] + TX, chlorantamine [500008-45-7] + TX, cyenopyrafen [560121-52-0] + TX, butylated fluoro ester [400882-07-7] + TX, pyrifluquinazon [337458-27- 2]+TX, schnott [187166-40-1+187166-15-0]+TX, spirotetramat [203313-25-1]+TX, fluramide nitrile [946578-00-3] +TX, butene fipronil [704886-18-0] + TX, cyfluthrin [915288-13-0] + TX, tetrafluthrin [84937-88-2] + TX, a kill The snail is selected from the group consisting of oxidized bis(tributyltin) (IUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] +TX, in addition to line Wei (999) + TX, acetonitrile copper arsenate [CCN] + TX, copper sulfate (172) + TX, triphenyl tin (347) + TX, iron phosphate (IUPAC name) (352) +TX, tetraacetaldehyde (518) + TX, chlorfenapyr (530) + TX, niclosamide (576) + TX, snail ethanolamine (576)+TX, pentachlorophenol (623)+TX, sodium pentachlorophenolate (623)+TX, thiazide (1412)+TX, thiodicarb (799)+TX, tributyltin oxide (913) ) +TX, snail net (1454) + TX, chlorpyrifos (840) + TX, triphenyl acetate (IUPAC name) (347) and triphenyl hydroxide (IUPAC name) (347) + TX , pyriprol [394730-71-3] + TX, a nematicide, is selected from the group consisting of AKD-3088 (compound code) + TX, 1,2-dibromo-3 - Chloropropane (IUPAC / Chemical Abstracts Name) (1045) + TX, 1,2-dichloropropane (IUPAC / Chemical Abstracts Name) (1062) + TX, 1,2-dichloropropane with 1,3-dichloro Propylene (IUPAC name) (1063) + TX, 1,3-dichloropropene (233) + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide (IUPAC / Chemical Abstracts Name) (1065) +TX, 3-(4-chlorophenyl)-5-methylrhodanine (Rhodanine) (IUPAC name) (980)+TX, 5-methyl-6-thioketo-1,3,5-thia two3-yl acetic acid (IUPAC name) (1286) + TX, 6-isopentenylaminopurine (general cross name) (210) + TX, avermectin (1) + TX, acetaminophen [CCN] +TX, cotton ring (15) + TX, aldicarb (16) + TX, oxygen aldicarb (863) + TX, AZ60541 (compound code) + TX, benclothiaz [CCN] + TX, benomyl (62 +TX, butyl daproterone (general cross name) + TX, sulphur phosphorus (109) + TX, carbofuran (118) + TX, carbon disulfide (945) + TX, butyl thiocarbacarb (119) +TX, trichloronitromethane (141) + TX, chlorpyrifos (145) + TX, in addition to line (999) + TX, cytokinin (universal cross name) (210) + TX, cotton (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamine phosphorus (1044) + TX, in addition to phosphorus (1051) + TX, two grams of phosphine (universal cross name) + TX, dimethoate (262) +TX, doramectin (general cross name) [CCN]+TX, avidin (291)+TX, emamectin benzoate (291)+TX, eplenomycin ( Universal cross name) [CCN]+TX, propylphosphorus (312)+TX, dibromoethylene (316)+TX, benzene phosphate (326)+TX, pyridoxamine (general cross name)+TX, Fonso Phosphorus (1158)+TX, thiazolyl (408)+TX, dandelion (1196)+TX, furfural (general cross name)[CCN]+T X, GY-81 (development code) (423) + TX, chlorpyrifos [CCN] + TX, methyl iodide (IUPAC name) (542) + TX, isamimidos (1230) + TX, chlorpyrifos (1231) +TX, ivermectin (general cross name) [CCN] + TX, furan methyl adenine (general cross name) (210) + TX, methyl quinone phosphorus (1258) + TX, Weibaimu (519 ) +TX, metam-potassium (universal cross name) (519) + TX, Wei is mu (519) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, mirabimycin Telluride (general cross name) [CCN] + TX, moxidectin (general cross name) [CCN] + TX, Fusarium lacquer (true) bacteria (Myrothecium verrucariaComposition (general cross name) (565) + TX, NC-184 (compound code) + TX, chlorpyrifos (602) + TX, phorate (636) + TX, phosphorus amine (639) + TX, Phosphorus [CCN]+TX, sulphur line phosphorus (general cross name)+TX, slavin (general cross name) [CCN]+TX, spinosad (737)+TX, tert-butyl (general cross name) +TX, tert-butyl phosphate (773)+TX, tetrachlorothiophene (IUPAC/Chemical Abstracts name) (1422)+TX, thiophene (general cross name)+TX, thiazolazine (1434)+TX, three Zolphos (820) + TX, oxazol (general cross name) + TX, xylenol [CCN] + TX, YI-5302 (compound code) and zeatin (general cross name) (210) + TX, fluensulfone [318290-98-1]+TX, a nitrification inhibitor, is selected from the group consisting of potassium ethyl xanthate [CCN] and trichloromethylpyridine (580) + TX. A plant activator selected from the group consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, thiabendazole (658), and Polygonum cuspidatum (Reynoutria sachalinensisThe extract (general cross name) (720) + TX, a rodenticide, is selected from the group consisting of 2-isoamyl-1,3-dihydroindoledione. (IUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino) benzenesulfonamide (IUPAC name) (748) + TX, α-chlorohydrin [CCN] + TX, aluminum phosphide ( 640)+TX, Antoine (880)+TX, arsenic trioxide (882)+TX, cesium carbonate (891)+TX, double-rat urea (912)+TX, Dalong (89)+TX, bromadiolone (91) +TX, bromine (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorflumente (140) + TX, vitamin D3 (general cross name) (850) + TX, chlortetracycline (1004) + TX, gram-killing mouse (1005) + TX, killing mouse (175) + TX, rat standing dead (1009) + TX, mouse gram (246) + TX, thief Ling (249)+TX, enemy mouse (273)+TX, ergocalciferol (301)+TX, flumurone (357)+TX, fluridamide (379)+TX, flurazepam (1183) +TX, flurazepam hydrochloride (1183) + TX, lindane (430) + TX, HCH (430) + TX, hydrogen cyanide (444) + TX, methyl iodide (IUPAC name) (542) + TX , hexachlorobenzene (430) + TX, magnesium phosphide (IUPAC name) (640) + TX, methyl bromide (537) + TX, rat Trane (1318) + TX, tetramine (1336) + TX, phosphorus Hydrogenation (I UPAC name) (640)+TX, phosphorus [CCN]+TX, murmurone (1341)+TX, potassium arsenite [CCN]+TX, rodent control (1371)+TX, red sea lycopene (1390) +TX, sodium arsenite [CCN]+TX, sodium cyanide (444)+TX, sodium fluoroacetate (735)+TX, strychnine (745)+TX, barium sulfate [CCN]+TX, kill Mouse spirit (851) and zinc phosphide (640) + TX, a synergist, are selected from the group consisting of the following components: 2-(2-butoxyethoxy)B Ester (IUPAC name) (934) + TX, 5-(1,3-benzodioxin-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903) + TX, gold Acacia and nerolidol (general cross name) (324) + TX, MB-599 (development code) (498) + TX, MGK264 (development code) (296) + TX, sunflower butyl ether (649) + TX, synergistic aldehyde (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, synergistic chrysanthemum (1393) + TX, sesame oil (1394) and Aachen (1406) + TX, a veterinary repellent, is selected from the group consisting of bismuth (32) + TX, chloralose (127) + TX, copper naphthenate [ CCN]+TX, copper oxychloride (171)+TX, diazinon (227)+TX, dicyclopentadiene (chemical name) (1069)+TX, Barium salt (422)+TX, biguanide acetate (422)+TX, chlorpyrifos (530)+TX, pyridin-4-amine (IUPAC name) (23)+TX, thiram (804)+TX, Miscellaneous (840)+TX, zinc naphthenate [CCN] and zinc dimethylformate (856)+TX, a viricide, is derived from Manan (general cross name) [CCN] and ribavirin (General cross name) [CCN] + TX selected from a group of substances, a wound protectant, selected from the group consisting of the following components, the composition of oxidized mercury (512) + TX, octyl isothiophene Ketone (590) and thiophanate-methyl (802) + TX, and biologically active compounds are selected from the group consisting of the following components: Nitroconazole (60207-31-0) + TX, double Benzotriazole [70585-36-3]+TX, carbendazole [116255-48-2]+TX, cyproconazole [94361-06-5]+TX, oxazole [119446-68-3] +TX, diniconazole [83657-24-3]+TX, epoxiconazole [106325-08-0]+TX, nitrile azole [114369-43-6]+TX, fluoroquinazole [136426-54- 5]+TX, flucarbazole [85509-19-9]+TX, fluconazole [76674-21-0]+TX, hexaconazole [79983-71-4]+TX, imazalil [35554- 44-0]+TX, imidazole [86598-92-7]+TX, inocastazole [125225-28-7]+TX, mexazole [1 25116-23-6]+TX, myclobutanil [88671-89-0]+TX, rice glutamate [101903-30-4]+TX, penconazole [66246-88-6]+TX, propyl sulfide Pyrazole [178928-70-6]+TX, aglycone [88283-41-4]+TX, prochloraz [67747-09-5]+TX, propiconazole [60207-90-1]+TX , flurazol [149508-90-7] + TX, tebuconazole [107534-96-3] + TX, tetrafluoroetherazole [112281-77-3] + TX, triazolone [43121-43-3 ]+TX, triazolol [55219-65-3]+TX, fluconazole [99387-89-0]+TX, sterilized azole [131983-72-7]+TX, cyprofenol [12771-68] -5]+TX, chloropyrimidinol [60168-88-9]+TX, fluoropyrimidinol [63284-71-9]+TX, acetaminophen sulfonate [41483-43-6]+TX, Dipyridol [5221-53-4] + TX, acetaminophen [23947-60-6] + TX, carbendazim [1593-77-7] + TX, fenpropidin [67306-00-7] +TX, butyl morpholine [67564-91-4] + TX, spirocyclam [118134-30-8] + TX, thirteen morpholine [81412-43-3] + TX, cyprodinil [ 121552-61-2]+TX, azoxystrobin [110235-47-7]+TX, pyrimethanil [53112-28-0]+TX, seed dressing [74738-17-3]+TX, bacterium Nitrile [131341-86-1]+TX, benzathine [71626-11-4]+TX, furosemide [57646-30-7]+TX, metalaxyl [57837-19-1]+TX, R metalaxyl [70630-17-0] + TX, furosemide [58810-48-3]+TX, ecstasy [77732-09-3]+TX, benomyl [17804-35-2]+TX, carbendazim [10605-21-7]+TX, microphone菌威[62732-91-6]+TX, Mai Suining [3878-19-1]+TX, thiabendazole [148-79-8]+TX, 乙菌利[84332-86-5]+TX , sclerotia [24201-58-9]+TX, iprodiurea [36734-19-7]+TX, myclozoline[54864-61-8]+TX, procymidone [32809-16-8]+TX , ethylene bacteria nuclear [50471-44-8] + TX, (S)-[3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluoro-phenyl)-isoZin-4-yl]-pyridin-3-yl-methanol (WO2010069881) + TX, 3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluoro-phenyl)-isoZin-4-yl]-pyridin-3-yl-methanol (WO2010069881) + TX, pyridine amide [188425-85-6] + TX, rust rust [5234-68-4] + TX, methylfurazan Amine [24691-80-3]+TX, Fudonin [66332-96-5]+TX, rust-free amine [55814-41-0]+TX, oxidized rust-free spirit [5259-88-1]+TX , pirimifloxacin [183675-82-3]+TX, thiazolamide [130000-40-7]+TX, biguanide salt [108173-90-6]+TX, multiguoding [2439-10-3 ][112-65-2](free base)+TX, bis-octylamine [13516-27-3]+TX, azoxystrobin [131860-33-8]+TX, ether myramine [149961-52-4 ]+TX, enestrobin {Proc. BCPC, Int. Congr., Glasgow, 2003, 1, 93} + TX, fluoxastrobin [361377-29-9] + TX, oxystrobin [143390-89] -0]+TX, phenoxystrobin [133408-50-1]+TX, trifloxystrobin [141517-21-7]+TX, orysastrobin[248593-16-0]+TX, picoxystrobin [117428] -22-5]+TX, pyraclostrobin [175013-18-0]+TX, melamine iron [14484-64-1]+TX, mancozeb [8018-01-7]+TX, generation Sen Manganese [12427-38-2]+TX, Daisenlian [9006-42-2]+TX, Bensen Zinc [12071-83-9]+TX, Fumeishuang [137-26-8]+TX, Dessen zinc [12122-67-7]+TX, zinc dimethylformate [137-30-4]+TX, enemy bacteria [2425-06-1]+TX, captan[133-06- 2]+TX, antibacterial [1085-98-9]+TX, chlorochlorobacteria [41205-21-4]+TX, sterilized Dan [133-07-3]+TX, toluene sulfonamide [731-27-1]+TX, Bordeaux mixture [8011-63-0]+TX, copper hydroxide [20427-59-2]+TX, copper oxychloride (1332-40-7)+TX, copper sulfate (coppersulfat) [7758- 98-7]+TX, copper oxide (copperoxid) [1317-39-1]+TX, mancozeb copper [53988-93-5]+TX, quinoline copper [10380-28-6]+TX, enemy螨普[131-72-6]+TX, fentanyl ester [10552-74-6]+TX, chlorpyrifos [17109-49-8]+TX, 瘟谷瘟净[26087-47-8]+ TX, Indigo [50512-35-1]+TX, proguanil [36519-00-3]+TX, fixed bacteria [13457-18-6]+TX, methyl chlorophosphate [57018-04] -9]+TX, acibenzolar-S-methyl[135158-54-2]+TX, carbendazim [101-05-3]+TX, benthiavalicarb[413615-35-7]+TX, ash limin [2079] -00-7]+TX, 螨 螨 [2439-01-2]+TX, chloroanisole [2675-77-6]+TX, chlorothalonil [1897-45-6]+TX, cyclofluoride Insectamine [180409-60-3]+TX, cymoxanil [57966-95-7]+TX, dichloronaphthylquinone [117-80-6]+TX, diclicymet[139920-32-4]+TX, Purobacillus [62865-36-5]+TX, chloramine [99-30-9]+TX, carbendazim [87130-20-9]+TX, olefin morpholine [110488-70-5] +TX SYP LI90(fluoromorpholine)[211867-47-9]+TX, dicyanone [3347-22-6]+TX, thiazolidin [162650-77-3]+TX, soil fungus [2593- 15-9]+TX, famoxadone [131807-57-3]+TX, fenamidone[161326-34-7]+TX, cyanamide [115852-48-7]+TX, triphenyltin [668] -34-8]+TX, azoxystrobin [89269-64-7]+TX, fluazinam [79622-59-6]+TX, fluridine[239110-15-7]+TX, sulfonate Amidoamine [106917-52-6]+TX, fenhexamid[126833-17-8]+TX, aluminum triethylphosphonate [39148-24-8]+TX, carbendazim [10004-44-1]+TX , 缬 威 [140923-17-7] + TX, IKF916 (cyanosin) [120116-88-3] + TX, spring leimycin [6980-18-3] + TX, sulfonamide [66952-49] -6]+TX, metrafenone[220899-03-6]+TX, pentosan (66063-05-6)+TX, tetrachlorophenylhydrazine [27355-22-2]+TX, polyoxin [11113 -80-7]+TX, thiabendazole [27605-76-1]+TX, downy mildew [25606-41-1]+TX, proquinazid[189278-12-4]+TX, praziquantel [57369 -32-1]+TX, quinoxaline [124495-18-7]+TX, pentachloronitrobenzene [82-68-8]+TX, sulfur [7704-34-9]+TX, tiadinil[223580 -51-6]+TX, imidazoline [72459-58-6]+TX, tricyclazole [41814-78-2]+TX, oxazinamide [26644-46-2]+TX, Jinggangmycin [ 37248- 47-8]+TX, carbendazim (RH7281) [156052-68-5]+TX, diacetylergicillin [374726-62-2]+TX, isopyrazam[881685-58-1]+TX, sedaxane [874967-67-6]+TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-dichloromethylene-1,2,3,4-tetrahydro) -1,4-Methyl-naphthyl-5-yl)-guanamine (disclosed in WO 2007/048556) + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid [ 2-(2,4-Dichlorophenyl)-2-methoxy-1-methyl-ethyl]-decylamine (disclosed in WO 2008/148570) + TX, 1-[4-[4-[ (5S) 5-(2,6-difluorophenyl)-4,5-dihydro-1,2-Zyrid-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl Ethylketone+TX, 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2Zyrid-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl Ethyl ketone [1003318-67-9] (both disclosed in WO 2010/123791, WO 2008/013925, WO 2008/013622 and WO 2011/051243, page 20) + TX, and 3-difluoromethyl- 1-Methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-guanamine (disclosed in WO 2006/087343) + TX.

As used herein, the term "composition" means a mixture or combination of different TX and (B) constituents, for example, in a single "premixed" form, and a combination of individual formulations of a single active ingredient. Spray blends (such as "tank-mix") can also be used in a combination of single active ingredients in a continuous manner (continuous mode is applied one after the other in a reasonable short-term period) , like every few hours or days). For the present invention to work, the order of application of ingredients TX and (B) is not critical.

Compositions made in accordance with the present invention may also contain more than one active ingredient (B), for example, when it is desired to expand the range of disease control. For example, combining two or three ingredients (B) with ingredient TX may be beneficial to agriculture. A composition containing a compound of the formula (I), azoxystrobin and cyproconazole is an example.

Among the different lists of the active ingredients in which the above formulas are mixed with TX, the compound of the formula (I) preferably uses the compound of Table 40 or 41.

In a mixture of the above compounds of the formula I (particularly selected from the above Tables 1-39, in combination with other insecticides, fungicides, herbicides, safeners, adjuvants and the like), the mixing ratio may be present Great difference (ideal range is 100:1 to 1:6000), especially 50:1 to 1:50, especially 20:1 to 1:20, even 10:1 to 1:10, and we It is known that these mixing ratios include, on the one hand, a weight ratio, and on the other hand, a molar ratio.

It may be advantageous to use the mixture in the above formulation (in this case, the "active ingredient" will be associated with the individual mixture of TX and the mixture partner).

The following non-limiting examples are illustrative of the invention described above (but not limiting). These professionals will be able to quickly identify appropriate changes from procedures related to reactants and reaction conditions and techniques. The references cited herein are incorporated by reference in their entirety.

Preparation Examples: In all the examples, the resulting isomers were excessive in the reaction mixture and/or product.

Example 1: Preparation of P.01

E-1-(6-methyl-pyridin-2-yl)-ethanone O-[3-(6-bromo-pyridin-2-yl)-propyl]-indole (150 mg) was added to contain fluorine Potassium (75 mg), diphenylphosphine oxide (5 mg), tris(dibenzylideneacetone)dipalladium (0) (5 mg) and lithium triisopropyl-2-pyridylborate (176 mg) (For preparation, please refer to Angew. Chem. Int. Ed. 2008, 47, 4695-4698) in dioxane (3 mL). After stirring at 100 ° C for 24 hours, the reaction mixture was diluted with ethyl acetate and washed with sodium bicarbonate (10% aqueous) and brine. The organic phase was dried <RTI ID=0.0></RTI> to <RTI ID=0.0>

Preparation of E-1-(6-methyl-pyridin-2-yl)-ethanone O-[3-(6-bromo-pyridin-2-yl)-propyl]-oxime

E-1-(6-methyl-pyridin-2-yl)-ethanone O-[3-(6-bromo-pyridin-2-yl)-prop-2-ynyl]-indole (921 mg) Dissolved in ethanol (30 mL). Platinum (IV) hydrate (49 mg) was added, and the reaction mixture was stirred under a hydrogen atmosphere for 90 minutes. Filtration, evaporation and purification of the reaction mixture with EtOAc afforded a colourless oil (671 mg). ^{1 H-NMR (CDCl3,400 MHz)} : 7.69 (d, 1H), 7.55 (t, 1H), 7.48 (t, 1H), 7.32 (d, 1H), 7.16 (d, 1H), 7.11 (d, 1H), 4.28 (t, 2H), 2.92 (t, 2H), 2.59 (s, 3H), 2.23 (s, 3H), 2.22 (m, 2H)

Preparation of E-1-(6-methyl-pyridin-2-yl)-ethanone O-[3-(6-bromo-pyridin-2-yl)-prop-2-ynyl]-oxime

Add 2,6-dibromo-pyridine (4.1 g) to THF containing E-1-(6-methyl-pyridin-2-yl)-ethanone O-prop-2-ynyl-indole (2.5 g) (80 mL) solution, then diisopropylamine (3.75 mL), bis(triphenylphosphine)palladium(II) chloride (364 mg) and copper (I) iodide (263 mg) were added. After stirring at room temperature for 16 hours, the reaction mixture was diluted with ethyl acetate and washed with sodium hydrogen sulfate (10% aqueous) and brine. The organic phase was dried <RTI ID=0.0> ¹ H-NMR (CDCl3, 400 MHz): 7.72 (d, 1H), 7.60-7.40 (m, 4H), 7.12 (d, 1H), 5.08 (s, 2H), 2.58 (s, 3H), 2.48 ( s, 3H).

Preparation of E-1-(6-methyl-pyridin-2-yl)-ethanone-O-prop-2-ynyl-indole

After 2-Ethyl-6-methyl-pyridine (1.5 g) was dissolved in ethanol (10 mL), sodium acetate (1.37 g) and O-propargyl-hydroxylamine hydrochloride (1.45 g) were then added. After stirring at rt for 16 h, EtOAc m. ¹ H-NMR (CDCl3, 400 MHz): 7.70 (d, 1H), 7.54 (t, 1H), 7.10 (d, 1H), 4.81 (s, 2H), 2.58 (s, 3H), 2.49 (s, 1H), 2.37 (s, 3H)

Example 2: Preparation of P.02

Sodium carbonate (49 mg) and 4-trimethylmethyl-3-butyn-2-one are added to contain 6-{3-[1-(6-methyl-pyridin-2-yl)-ar-(E) -ethylaminooxy]-propyl}-pyridine-2-carboxamidine hydrochloride (80 mg) in acetonitrile (5 mL). After stirring at 80 ° C for 72 hours, the reaction mixture was diluted with ethyl acetate and washed with sodium hydrogen carbonate (10% aqueous) and brine. The organic phase was dried <RTI ID=0.0></RTI> to <RTI ID=0.0>

Preparation of 6-{3-[1-(6-methyl-pyridin-2-yl)-i-(E)-ethylaminooxy]-propyl}-pyridine-2-carboxamidine hydrochloride

Sodium methoxide (210 mg) was added to contain 6-{3-[1-(6-methyl-pyridin-2-yl)-i-(E)-ethylaminooxy}-propyl}-pyridine-2 - Carbononitrile (1.06 g) in methanol (40 mL). After stirring at room temperature for 72 hours, ammonium chloride (230 mg) was added, and then the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was evaporated and the residue was crystalljjjjjjjjjj

Preparation of 6-{3-[1-(6-methyl-pyridin-2-yl)-i-(E)-ethylaminooxy]-propyl}-pyridine-2-carbonitrile

6-{3-[1-(6-Methyl-pyridin-2-yl)-i-(E)-ethylaminooxy]-prop-1-ynyl}-pyridine-2-carbonitrile (128 Mg) was dissolved in ethanol (5 mL). Palladium (5% on charcoal; 10 mg) was added and the reaction mixture was stirred under a hydrogen atmosphere for 5 hours. After filtering the reaction mixture and evaporating water, a yellow oil (118 mg) was obtained. 1H-NMR (CDCl3, 400 MHz): 7.73 (t, 1H), 7.68 (d, 1H), 7.61-7.53 (m, 2H), 7.42 (d, 1H), 7.12 (d, 1H), 4.29 (t) , 2H), 3.00 (t, 2H), 2.59 (s, 3H), 2.32 (s, 3H), 2.23 (m, 2H)

Preparation of 6-{3-[1-(6-methyl-pyridin-2-yl)-i-(E)-ethylaminooxy]-prop-1-ynyl}-pyridine-2-carbonitrile

2-Bromo-6-cyanopyridine (1.57 g) and E-1-(6-methyl-pyridin-2-yl)-ethanone O-prop-2-ynyl-indole (1.62 g) were dissolved in In THF (40 mL). Diisopropylamine (2.42 mL), dichlorobis(triphenylphosphine)palladium(II) (181 mg) and copper (I) iodide (131 mg) were added. After stirring at room temperature for 16 hours, the reaction mixture was diluted with ethyl acetate and washed with sodium hydrogen sulfate (10% aqueous) and brine. The organic phase was dried <RTI ID=0.0></RTI> ¹ H-NMR (CDCl3, 400 MHz): 7.80 (t, 1H), 7.71 (d, 1H), 7.63 (m, 2H), 7.56 (t, 1H), 7.12 (d, 1H), 5.08 (s, 2H), 2.58 (s, 3H), 2.48 (s, 3H).

Example 3: Preparation of P.03

Sodium carbonate (84 mg) and acetamidine hydrochloride (37 mg) were added to contain 1-(6-{3-[1-(6-methyl-pyridin-2-yl)-i-(E)-ethylamine Oxy]-propyl}-pyridin-2-yl)-propynone (110 mg) in acetonitrile. After stirring at 80 ° C for 3 hours, the reaction mixture was filtered and evaporated. The residue was purified by chromatography over EtOAc (EtOAc)

Preparation of 1-(6-{3-[1-(6-methyl-pyridin-2-yl)-i-(E)-ethylaminooxy]-propyl}-pyridin-2-yl)-propane Propargyl ketone

1,1,1-tris(ethyloxy)-1,1-dihydro-1,2-phenyliodonium-3-(1H)-one (1.48 g) was added to contain E-1-(6- Methyl-pyridin-2-yl)-ethanone O-{3-[6-(1-hydroxy-prop-2-ynyl)-pyridin-2-yl]-propyl}-indole (870 mg) In dichloromethane (45 mL). After stirring at room temperature for 4 hours, sodium hydrogencarbonate (20 mL; 20% aqueous solution) and sodium thiosulfate (20 mL; 30% aqueous solution) were added. After stirring for 40 minutes, the org. 1H-NMR (CDCl3, 400 MHz): 7.97 (d, 1H), 7.76 (t, 1H), 7.66 (d, 1H), 7.54 (t, 1H), 7.41 (d, 1H), 7.10 (d, 1H) ), 4.32 (t, 2H), 3.52 (s, 1H), 3.06 (t, 2H), 2.57 (s, 3H), 2.41 (s, 3H), 2.28 (m, 2H).

Preparation of E-1-(6-methyl-pyridin-2-yl)-ethanone O-{3-[6-(1-hydroxy-prop-2-ynyl)-pyridin-2-yl]-propyl }-肟

At 6-{3-[1-(6-methyl-pyridin-2-yl)-i-(E)-ethylaminooxy]-propyl}-pyridine-2 at a temperature of -65 °C - A solution of formaldehyde (420 mg) in THF (15 mL) over EtOAc over EtOAc (EtOAc &lt After stirring at -65 ° C for 2 hours, ammonium chloride (2 mL; 15% in water) was added. The reaction mixture was diluted with ethyl acetate and washed with sodium bicarbonate (10% aqueous) and brine. The organic phase was dried <RTI ID=0.0> ¹ H-NMR (CDCl3, 400 MHz): 7.68 (m, 2H), 7.58 (t, 1H), 7.45 (d, 2H), 7.19 (d, 1H), 7.11 (d, 1H), 5.47 (s, Broad, 1H), 5.19 (s, broad, 1H), 4.29 (t, 2H), 2.98 (t, 2H), 2.58 (s, 3H), 2.55 (d, 1H), 2.33 (s, 3H), 2.25 (m, 2H).

Preparation of 6-{3-[1-(6-methyl-pyridin-2-yl)-i-(E)-ethylaminooxy]-propyl}-pyridine-2-carbaldehyde

6-{3-[1-(6-Methyl-pyridin-2-yl)-i-(E)-ethylaminooxy]-prop-1-ynyl}-pyridine-2-carbaldehyde (1.13 g ) Dissolved in ethanol (40 mL). Platinum (IV) hydrate (80 mg) was added, and the reaction mixture was stirred under a hydrogen atmosphere for 3 hours. Filtration, evaporation and purification of the reaction mixture with EtOAc afforded a yellow oil (235 mg). ¹ H-NMR (CDCl3, 400 MHz): 10.05 (s, 1H), 7.79 (m, 2H), 7.67 (d, 1H), 7.54 (t, 1H), 7.42 (d, 1H), 7.10 (d, 1H), 4.30 (t, 2H), 3.03 (t, 2H), 2.47 (s, 3H), 2.31 (s, 3H), 2.25 (m, 2H).

Preparation of 6-{3-[1-(6-methyl-pyridin-2-yl)-i-(E)-ethylaminooxy]-prop-1-ynyl}-pyridine-2-carbaldehyde

6-Bromo-pyridine-2-carbaldehyde (2.5 g) and 1-(6-methyl-pyridin-2-yl)-ethanone O-prop-2-ynyl-indole (2.53 g) were dissolved in THF (80) In mL). Diisopropylamine (3.79 mL), dichlorobis(triphenylphosphine)palladium(II) (283 mg) and copper (I) iodide (205 mg) were added. After stirring at room temperature for 6 hours, the reaction mixture was diluted with ethyl acetate and washed with sodium hydrogen sulfate (10% aqueous) and brine. The organic phase was dried <RTI ID=0.0> ¹ H-NMR (CDCl3, 400 MHz): 10.05 (s, 1H), 7.90 (d, 1H), 7.85 (t, 1H), 7.70 (m, 2H), 7.55 (t, 1H), 7.12 (d, 1H), 5.10 (s, 2H), 2.68 (s, 3H), 2.40 (s, 3H).

Example 4: Preparation of P.11

E-1-(6-methyl-pyridin-2-yl)-ethanone-O-[3-(4'-methoxy-6'-methyl-[2,2']bipyridin-6 -yl)-prop-2-ynyl]-indole (908 mg) was dissolved in tetrahydrofuran (THF) (15 ml). Palladium (10% on charcoal; 20 mg) was added and the reaction mixture was stirred under a hydrogen atmosphere for 16 h. The reaction mixture was filtered and evaporated to give 1-(6-methyl-pyridin-2-yl)-ethanone-O-[3-(4'-methoxy-6'-methyl-[2,2' a beige solid of bispyridyl-6-yl)-propyl]-indole having a melting point of 84-86 °C.

Preparation of E-1-(6-methyl-pyridin-2-yl)-ethanone-O-[3-(4'-methoxy-6'-methyl-[2,2']bipyridyl- 6-yl)-prop-2-ynyl] -oxime

6'-Bromo-4-methoxy-6-methyl-[2,2']bipyridyl (1.1 g) and E-1-(6-methyl-pyridin-2-yl)-ethanone -O-prop-2-ynyl-indole (1.12 g) was dissolved in tetrahydrofuran (THF) (20 ml). Diisopropylamine (3.9 g), dichlorobis(triphenylphosphine)palladium(II) (56 mg) and copper (I) iodide (61 mg) were added. After stirring at a temperature of 55 ° C for 1 hour, the reaction mixture was poured into water, extracted with ethyl acetate and washed with brine. The organic phase is dried over sodium sulfate, concentrated and purified by chromatography over silica to afford 1-(6-methyl-pyridin-2-yl)-ethanone-O-[3-(4'-- A beige solid of oxy-6'-methyl-[2,2'] bispyridin-6-yl)-prop-2-ynyl]-indole having a melting point of 119-120 °C.

Preparation of 6'-bromo-4-methoxy-6-methyl-[2,2']bipyridyl

Take potassium carbonate (11.5 g) and methyl iodide (14.7 g), add acetone containing 6'-bromo-6-methyl-[2,2'] bispyridin-4-ol (11 g) (80 ml) ) solution. After stirring overnight, the reaction mixture was poured into water, extracted with ethyl acetate and brine. The organic phase is dried over sodium sulfate, concentrated and purified by chromatography over EtOAc (EtOAc) Solid, melting point 103-104 ° C.

Preparation of 6'-bromo-6-methyl-[2,2']bispyridin-4-ol

Diisopropylethylamine (34.7 g) and trimethylsulfonyl trifluoromethanesulfonate (74.6 g) were added at 0 ° C, and added to contain 6-bromo-pyridine-2-carboxylic acid-(Z a solution of 1-methyl-3-oxo-but-1-enyl)-guanamine (19 g) in 1,2-dichloroethane (700 ml). The reaction mixture was stirred overnight under reflux and then poured into aq. The beige solid of 6'-bromo-6-methyl-[2,2']bispyridin-4-ol was obtained by filtration and concentrated to crystallised from ethyl acetate.

Preparation of 6-bromo-pyridine-2-carboxylic acid-((Z)-1-methyl-3-oxo-but-1-enyl)-decylamine

Ethylene dichloride (11.6 g) was added dropwise to a mixed solution of 6-bromo-pyridine-2-carboxylic acid (15.4 g) and a catalytic amount of DMF in dichloromethane (150 ml). The reaction mixture was stirred at room temperature for 30 minutes and stirred under reflux for 30 minutes, then concentrated to give a beige solid of 6-bromo-pyridine-2-carboxylic acid chloride and dissolved in -20 ° C. Dichloromethane (80 ml) was added dropwise to dichloromethane (70 ml) and triethylamine (9.3) containing (Z)-4-amino-pent-3-en-2-one (7.6 g). g) in the solution. The reaction mixture was stirred at room temperature overnight then poured into a saturated bicarbonate solution and extracted with dichloromethane and dried over sodium sulfate. After purification by cerium oxide, 6-bromo-pyridine-2-carboxylic acid-((Z)-1-methyl-3-oxo-but-1-enyl)-decylamine is obtained by filtration and concentration. The yellow solid has a melting point of 113-114 ° C.

Example 5: Preparation of P.14

1-(6-Methyl-pyridin-2-yl)-ethanone-O-[3-(4'-benzyloxy-6'-methyl-[2,2']bipyridyl-6- The base)-prop-2-ynyl]-indole (1.1 g) was dissolved in tetrahydrofuran (THF) (20 ml). Palladium (10% on charcoal; 180 mg) was added and the reaction mixture was stirred under a hydrogen atmosphere for 16 hours. After purification by cerium oxide, the reaction mixture was filtered and evaporated to give 1-(6-methyl-pyridin-2-yl)-ethanone-O-[3-(4'-hydroxy-6'-methyl- [2,2'] Bipyridyl-6-yl)-propyl]-indole oil.

Preparation of E-1-(6-methyl-pyridin-2-yl)-ethanone-O-[3-(4'-benzyloxy-6'-methyl-[2,2']bipyridyl -6-yl)-prop-2-ynyl]-oxime

4-Benzyloxy-6'-bromo-6-methyl-[2,2']bipyridyl (1.05 g) and E-1-(6-methyl-pyridin-2-yl)-B Keto-O-prop-2-ynyl-indole (835 mg) was dissolved in tetrahydrofuran (THF) (30 ml). Diisopropylamine (2.99 g), dichlorobis(triphenylphosphine)palladium(II) (92 mg) and copper (I) iodide (92 mg) were added. After stirring at a temperature of 55 ° C for 3 hours, the reaction mixture was poured into water, extracted with ethyl acetate and washed with brine. The organic phase is dried over sodium sulfate, concentrated and purified by chromatography using EtOAc (EtOAc) to afford 1-(6-methyl-pyridin-2-yl)-ethanone-O-[3-(4'-benzene A brown oil of methoxy-6'-methyl-[2,2'] bispyridin-6-yl)-prop-2-ynyl]-indole.

Preparation of 4-benzyloxy-6'-bromo-6-methyl-[2,2']bipyridyl

Potassium carbonate (0.61 g) and benzyl bromide (0.75 g) were added, and DMF (30) containing 6'-bromo-6-methyl-[2,2']bipyridin-4-ol (1.4 g) was added. Ml) solution. After stirring overnight, the reaction mixture was poured into water, extracted with ethyl acetate and brine. The organic phase is dried over sodium sulfate, concentrated and purified by chromatography over silica to afford 4-benzyloxy-6'-bromo-6-methyl-[2,2']bipyridyl Color solid, melting point 96-97 ° C.

Example 6: Preparation of P.16

E-1-(6-Methyl-pyridin-2-yl)-ethanone-O-[3-(4'-hydroxy-6'-methyl-[2,2']bipyridyl-6- The base)-propyl]-oxime (150 mg) was stirred with phosphorus chlorochloride (3 ml) at 55 ° C for 2 hours. After concentration, ethyl acetate (30 ml) was added with water (50 ml) then 2N NaOH was added until the solution was neutral. The reaction mixture was extracted with ethyl acetate and washed with brine, and then dried over sodium sulfate, and then concentrated to give 1-(6-methyl-pyridin-2-yl)-ethanone-O-[3-(4) '-Chloro-6'-methyl-[2,2']bispyridyl-6-yl)-propyl]-indole, which was recrystallized from tert-butyl methyl ether, m.p.: 53-54.

Example 7: Preparation of P.39

Sodium methyl mercaptan (26 mg) was added to contain E-1-(6-methyl-pyridin-2-yl)-ethanone-O-[3-(4'-chloro-6'-methyl-[ 2,2']bipyridin-6-yl)-propyl]-indole (110 mg) in DMF (4 ml). After stirring at 45 ° C for 2 hours, the reaction mixture was poured into water, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, dried and concentrated, 6-Methyl-pyridin-2-yl)-ethanone-O-[3-(4'-methylsulfonyl-6'-methyl-[2,2']bipyridyl-6-yl) - propyl]-indole as a beige solid, m.p. 76-77.

Example 8: Preparation of P.44

Add p-toluenesulfonic acid monohydrate (8 mg) to contain O-[3-(4'-methoxy-[2-2']bipyridin-6-yl)-propyl]-hydroxylamine (180 Mg) and 1-(4,6-dimethylpyrimidin-2-yl)ethanone (100 mg) in ethanol (15 mL). After stirring at room temperature for 3 hours, the reaction mixture was poured into water, extracted with dichloromethane and washed with brine. The organic phase was dried over sodium sulfate, concentrated and purified by chromatography on a silicon dioxide, to obtain a pale yellow resin ^{(210 mg) 1 H-NMR} (CDCl3,400 MHz): 8.24 (d, 1H), 7.87 ( s, 1H), 7.72 (t, 1H), 7.21 (d, 1H), 7.00 (s, 1H), 6.70 (s, 1H), 4.49 (t, 2H), 3.95 (s, 3H), 3.02 (t , 2H), 2.59 (s, 3H), 2.53 (s, 6H), 2.38 (s, 3H), 2.31 (m, 2H).

Preparation of O-[3-(4'-methoxy-[2-2']bispyridin-6-yl)-propyl]-hydroxylamine

Hydrazine hydrate (140 mg) was added to contain 2-[3-(4'-methoxy-6'-methyl-[2,2']bipyridin-6-yl)-propoxy]-isoindole A solution of 哚-1,3-dione (560 mg) in ethanol (25 mg). After 1 minute, the reaction mixture was stirred at room temperature for 2 hours. Pour it onto the water (80 mL) and continue stirring, then add 4N NaOH solution until pH 14 is reached. The reaction mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and concentrated to give a pale yellow powder (340 mg). ¹ H-NMR (CDCl3, 400 MHz): 8.2 (d, 1H), 7.8 (d, 1H), 7.7 (t, 1H), 7.15 (d, 1H), 6.7 (d, 1H), 5.4 (s, 2H), 3.9 (s, 3H), 3.75 (t, 2H), 2.9 (t, 2H), 2.55 (s, 3H), 2.1 (m, 2H).

Preparation of 2-[3-(4'-methoxy-6'-methyl-[2,2']bispyridin-6-yl)-propoxy]-isoindole-1,3-dione

Palladium on carbon (10%; 120 mg) was added to contain 2-[3-(4'-methoxy-6'-methyl-[2,2']bipyridyl-6-yl)-propan-2- A solution of alkynyloxy]-isoindole-1,3-dione (1.27 g) in THF (120 mL). The reaction mixture was stirred under a hydrogen atmosphere for 3.5 hours. After filtration, evaporation and purification of cerium oxide, a pale yellow powder (580 mg) was obtained. ¹ H-NMR (CDCl3, 400 MHz): 8.2 (d, 1H), 7.8 (m, 6H), 7.35 (s, 1H), 6.7 (d, 1H), 4.3 (t, 2H), 3.95 (s, 3H), 3.1 (t, 2H), 2.6 (s, 3H), 2.8 (q, 2H).

Preparation of 2-[3-(4'-methoxy-6'-methyl-[2,2']bipyridin-6-yl)-prop-2-ynyloxy]-isoindole-1, 3-diketone

N-hydroxybenzoquinone imine (0.675 g) was added in portions at 0 ° C to contain 3-(4'-methoxy-6'-methyl-[2,2']bipyridin-6-yl. - a solution of -prop-2-yn-1-ol (1.05 g) in THF (30 mL). Triphenylphosphine (1.19 g) was added, followed by the dropwise addition of diisopropyl azodicarboxylate (0.92 g) at 0 °C. The reaction mixture was diluted with a THF (15 mL) solution and then stirred at room temperature for 3 hr. After evaporation, a methanol-water mixture (60 mL; 5:1 v/v) was added. After filtration, it was washed with a filtrate and dried to give a beige powder (1.31 g). ¹ H-NMR (CDCl3, 400 MHz): 8.4 (d, 1H), 7.9 (d, 2H), 7.75 (m, 4H), 7.5 (d, 1H), 6.7 (d, 1H), 5.15 (s, 2H), 3.95 (s, 3H), 2.5 (s, 3H).

Preparation of 3-(4'-methoxy-6'-methyl-[2,2']bispyridin-6-yl)-2-propyn-1-ol

The cuprous iodide (40 mg) and tetrakis(triphenylphosphine)palladium(0) (120 mg) were added to contain 6'-bromo-4-methoxy-6-methyl-[2] under argon. , 2'] in a solution of bipyridyl (2.9 g) in toluene (50 mL). Propargyl alcohol (0.87 g) was added dropwise followed by diisopropylamine (2.6 g). The reaction mixture was stirred at room temperature overnight. It was then poured onto water, diluted with ethyl acetate and filtered through Celite. The organic phase was washed with brine and dried over sodium sulfate. ¹ H-NMR (CDCl3, 400 MHz): 8.4 (d, 1H), 7.8 (m, 2H), 7.4 (d, 1H), 6.7 (d, 1H), 4.55 (s, 2H), 3.95 (s, 3H), 2.55 (s, 3H), 2.4 (s, 1H).

Preparation of 1-(4,6-dimethylpyrimidin-2-yl)ethanone

Hydrochloric acid was added to water (1M; 15 mL), and then a mixture of &lt;RTI ID=0.0&gt;&gt; After stirring at room temperature for 16 hours, the reaction mixture was diluted with water, the organic phase was separated, and the aqueous phase was extracted with tert-butyl methyl ether. The combined organic phase was washed with water, dried over sodium sulfate, concentrated and purified with EtOAc (EtOAc) (EtOAc:EtOAc: (s, 3H), 2.59 (s, 6H).

Preparation of 1-(4,6-dimethylpyrimidin-2-yl)ethanone

Tributyl (1-ethoxyethylene)stannane (15.4 mL) was added to a solution containing 2-chloro-4,6-dimethyl-pyrimidine (5 g) in dimethylformamide (70 mL) in. After stirring at room temperature for 30 minutes, bis(triphenylphosphine)palladium(II) chloride (500 mg) was added. The reaction mixture was stirred at 100 ° C for 43 hours and then cooled to 25 ° C. Then tert-butyl methyl ether (210 mL) was added and an aqueous solution (40 mL) of potassium fluoride (100 g) was added. After stirring at room temperature for 1 hour, the reaction mixture was diluted with water and the organic phase was separated, and the aqueous phase was extracted with tert-butyl methyl ether and dichloromethane. The combined organic phases were washed with water and a sodium bicarbonate solution (15%), dried over sodium sulfate, concentrated and purified with EtOAc. 1H-NMR (CDCl3, 400 MHz): 6.96 (s, 1H), 5.62 (d, 1H), 4.60 (d, 1H), 4.07 (q, 2H), 2.53 (s, 6H), 1.50 (t, 3H) ).

Example 9: Preparation of P.45

E-1-(6-methyl-2-pyridyl)-N-[3-[2-(6-methyl-2-pyridyl)pyrimidin-4-yl]prop-2-ynyloxy]B The imine (240 mg) was dissolved in ethanol (45 mL). Platinate (40 mg) was added, and the reaction mixture was stirred under a hydrogen atmosphere for 2 hours. Filtration and evaporation of the reaction mixture to give E-1-(6-methyl-2-pyridyl)-N-[3-[2-(6-methyl-2-pyridyl)pyrimidin-4-yl]propoxy A yellow oil of ethyl iminoamine (114 mg). ¹ H-NMR (CDCl3, 400 MHz): 8.82 (d, 1H), 8.32 (d, 1H), 7.73 (t, 1H), 7.67 (d, 1H), 7.53 (t, 1H), 7.27 (d, 1H), 7.19 (d, 1H), 7.09 (d, 1H), 4.33 (t, 2H), 3.02 (t, 2H), 2.73 (s, 3H), 2.57 (s, 3H), 2.33 (s, 3H) ), 2.29 (m, 2H).

Preparation of E-1-(6-methyl-2-pyridyl)-N-[3-[2-(6-methyl-2-pyridyl)pyrimidin-4-yl]prop-2-ynyloxy] Ethyl imine

4-Chloro-2-(6-methyl-2-pyridyl)pyrimidine (according to "Bioorganic & Medicinal Chemistry Letters", Vol. 19, No. 8, pp. 2277-2281, 2009 In the manner described in the above, 1.0 g) and 1-(6-methyl-pyridin-2-yl)-ethanone O-prop-2-ynyl-indole (1.1 g) were dissolved in tetrahydrofuran (THF) solution ( 25 ml). Diisopropylamine (1.4 mL), dichlorobis(triphenylphosphine)palladium(II) (102 mg) and copper (I) iodide (74 mg) were added. After stirring at room temperature for 16 hours, the reaction mixture was diluted with ethyl acetate and washed with sodium hydrogen sulfate (10% aqueous) and brine. The organic phase was dried with EtOAc (EtOAc m. 1H-NMR (CDCl3, 400 MHz): 8.91 (d, 1H), 8.32 (d, 1H), 7.73 (m, 2H), 7.56 (t, 1H), 7.38 (d, 1H), 7.28 (d, 1H) ), 7.12 (d, 1H), 5.10 (s, 2H), 2.72 (s, 3H), 2.58 (s, 3H), 2.40 (s, 3H).

Example 10: Preparation of P.54

Taking cesium carbonate (106 mg), trimethylboroxycycloalkane (50% by weight in tetrahydrofuran (THF), 3.5 M; 0.03 mL) and (1,1'-bis(diphenylphosphino)-ferrocene Palladium(II) chloride (7 mg) was added to contain 1-(6-methyl-pyridin-2-yl)-ethanone-O-[3-(9-chloro-[1,10]morpholine -2-yl)-propyl]-indole (33 mg) in dioxane (4 mL). After stirring at 95 ° C for 15 min, the reaction mixture was poured into water to ethyl acetate The ester is extracted and washed with brine. The organic phase is dried over sodium sulfate, concentrated and purified by chromatography over silica to afford 1-(6-methyl-pyridin-2-yl)-ethanone-O-[3 An oil of (9-methyl-[1,10]morpholino-2-yl)-propyl]-indole.

Example 11: Preparation of P.55

1-(6-Methyl-pyridin-2-yl)-ethanone-O-[3-(9-chloro-[1,10]morphoxalin-2-yl)-prop-2-ynyl]- The hydrazine (70 mg) was dissolved in tetrahydrofuran (THF) (12 mL). Palladium (10% on charcoal; 30 mg) was added and the reaction mixture was stirred under a hydrogen atmosphere for 3 hours. After purification by cerium oxide, the reaction mixture was filtered and evaporated to give 1-(6-methyl-pyridin-2-yl)-ethanone-O-[3-(9-chloro-[1,10] An oil of oxa-2-yl)-propyl]-indole.

Preparation of E-1-(6-methyl-pyridin-2-yl)-ethanone-O-[3-(9-chloro-[1,10]morpholino-2-yl)-prop-2-yne Base]-肟

2,9-Dichloro-[1,10]morpholine (0.46 g) and E-1-(6-methyl-pyridin-2-yl)-ethanone-O-prop-2-ynyl-indole (382 mg) was dissolved in tetrahydrofuran (THF) (5 mL). Diisopropylamine (1.88 g), dichlorobis(triphenylphosphine)palladium(II) (57 mg) and copper (I) iodide (58 mg) were added. After stirring at 55 ° C for 3 hours, the reaction mixture was poured into water, extracted with ethyl acetate and washed with brine. The organic phase is dried over sodium sulfate, concentrated and purified by chromatography using EtOAc to afford 1-(6-methyl-pyridin-2-yl)-ethanone-O-[3-(9-chloro- [1,10] Brown morpholin-2-yl)-prop-2-ynyl]-indole as a brown solid.

Table 40: NMR data for compounds of formula (I):

Table 41: Physical data of the compounds of formula (I):

LC method used

Method A

Waters' automatic purification system: 2767 sample manager, 2489 UV/visible detector, 2545 quaternary gradient module.

Column: Phenomenex Synergi C18 reverse phase, 4 μm particle size, 80 , 75 x 30.00 mm, 100 mg of product dissolved in the injected DMF

DAD wavelength (nm): 220 and 254

Solvent gradient:

A=Fluka Analytical

B = Fluka Analytical for preparative high performance liquid chromatography

LC-MS method used

ZMD method

American Waters ZMD mass spectrometer (single quadrupole mass spectrometer)

Instrument parameters:

Ionization method: electric spraying

Polarity: positive ion

Capillary (kV) 3.80, injection cone (V), extractor (V) 3.00, source temperature (°C) 150, desolvation gas temperature (°C) 350, injection cone gas flow rate (L/Hr) off, off Solvent gas flow rate (L/Hr) 600

Quality range: 100 to 900 Da

Agilent's HP 1100 HPLC: solvent deaerator, binary pump, heated oven and diode array detector.

Column: Ferno Gmini C18, 3 mm particle size, 110 30 x 3 mm, temperature: 60 ° C

DAD wavelength range (nm): 200 to 500

Solvent gradient:

A=water+0.05% HCOOH

B = acetonitrile / methanol (4:1, v: v) + 0.04% HCOOH

ZCQ method

American Waters ZQ mass spectrometer (single quadrupole mass spectrometer)

Instrument parameters:

Ionization method: electric spraying

Polarity: positive ion

Capillary (kV) 3.00, injection cone (V) 30.00, extractor (V) 2.00, source temperature (°C) 100, desolvation gas temperature (°C) 250, injection cone gas flow rate (L/Hr) 50, off Solvent gas flow rate (L/Hr) 400

Quality range: 100 to 900 Da

Agilent's HP 1100 HPLC: solvent deaerator, quaternary pump (ZCQ) / binary pump (ZCQ), heated oven and diode array detector.

Column: Ferno Gmini C18, 3 mm particle size, 110 , 30 x 3 mm

Temperature: 60 ° C

DAD wavelength range (nm): 200 to 500

Solvent gradient:

A=water+0.05% HCOOH

B = acetonitrile / methanol (4:1, v: v) + 0.04% HCOOH

ZDQ method

American Waters ZQ mass spectrometer (single quadrupole mass spectrometer)

Instrument parameters:

Ionization method: electric spraying

Polarity: positive ion

Capillary (kV) 3.00, injection cone (V) 30.00, extractor (V) 2.00, source temperature (°C) 100, desolvation gas temperature (°C) 250, injection cone gas flow rate (L/Hr) 50, off Solvent gas flow rate (L/Hr) 400

Quality range: 100 to 900 Da

Agilent's HP 1100 HPLC: solvent deaerator, binary pump (ZCQ) / binary pump (ZDQ), heated oven and diode array detector.

Column: Ferno Gmini C18, 3 mm particle size, 110 , 30 x 3 mm, temperature: 60 ° C

DAD wavelength range (nm): 200 to 500

Solvent gradient:

A=water+0.05% HCOOH

B = acetonitrile / methanol (4:1, v: v) + 0.04% HCOOH

U method

American Waters ACQUITY SQD Mass Spectrometer (Single Quadrupole Mass Spectrometer)

Ionization method: electric spraying

Polarity: positive ion

Capillary (kV) 3.00, injection cone (V) 20.00, extractor (V) 3.00, source temperature (°C) 150, desolvation gas temperature (°C) 400, injection cone gas flow rate (L/Hr) 60, off Solvent gas flow rate (L/Hr) 700

Quality range: 100 to 800 Da

DAD wavelength range (nm): 210 to 400

Waters ACQUITY UPLC method with the following HPLC gradient conditions

Solvent gradient:

A: water/methanol (9:1, v:v) + 0.1% HCOOH

B: acetonitrile + 0.1% HCOOH

Column type: Waters ACQUITY UPLC HSS T3; column length: 30 mm; column inner diameter: 2.1 mm, particle size: 1.8 microns; temperature: 60 °C.

OA_2min_30V

Waters SQD mass spectrometer (single quadrupole mass spectrometer): ionization method: electrospray; polarity: positive ion and negative ion; capillary (kV): 3.00; injection cone (V): 30.00; extraction (V): 2.00; source temperature (°C): 150; desolvation gas temperature (°C): 250; injection cone gas flow rate (L/Hr): 0; desolvation gas flow rate (L/Hr): 650; Quality range: 100 to 900 Da

American company Waters Acquity UPLC: Binary Pump, Heating Cartridge and Diode Array Detector; Solvent Degassing Agent, Binary Pump, Heating Column Box and Diode Array Detector; Column: Ferno Gmini C18 , 3 m, 30 x 2 mm; temperature: 60 ° C; DAD wavelength range (nm): 210 to 500

Solvent gradient:

A = water + 5% methanol + 0.05% HCOOH

B = acetonitrile + 0.05% HCOOH

OA_3min_30V

Waters ZQ mass spectrometer (single quadrupole mass spectrometer): ionization method: electrospray; polarity: positive ion and negative ion; capillary (kV): 3.00; injection cone (V): 30.00; extraction (V): 2.00; source temperature (°C): 100; desolvation gas temperature (°C): 250; injection cone gas flow rate (L/Hr): 50;

Desolvent gas flow rate (L/Hr): 400; mass range: 100 to 900 Da Agilent's HP 1100 HPLC: solvent deaerator, binary pump, heated oven and diode array detector; column: Ferno Gmini C18, 3 m, 30 x 3 mm; temperature: 60 ° C; DAD wavelength range (nm): 210 to 500; solvent gradient:

A = water + 5% MeOH + 0.05% HCOOH

B = acetonitrile + 0.05% HCOOH

Biological examples:

Phytophthora infestans / Tomato / Leaf Disc Prevention (late blight)

Tomato leaf discs were placed on water agar on a multi-well plate (24-well plate) and sprayed with a test compound diluted with water at a rate of 200 ppm. One day after application, the leaf discs were inoculated with a spore suspension of the fungus. The inoculated leaf discs were cultured in a climate chamber at 16 ° C and 75% relative humidity in a 24-hour dark, followed by 12/12 hours (light/dark) illumination, and the activity of the compounds was evaluated as a percentage of disease control, and Compared to untreated cases (when untreated test leaf discs (5 to 7 days after administration) have appropriate disease levels). The following compounds can inhibit at least 80% of potato rot pathogens : P.13, P.44

Plasmopara viticola / grape / leaf disc prevention (late blight)

The grape leaf discs were placed on water agar on a multi-well plate (24-well plate) and sprayed with a test compound diluted with water. One day after application, the leaf discs were inoculated with a spore suspension of the fungus. The inoculated leaf discs were incubated at 19 ° C and 80% relative humidity in a climate chamber at 12/12 hours (light/dark) illumination, and the activity of the compounds was assessed as a percentage of disease control and untreated Compared to the case (when an untreated check leaf (6 to 8 days after application) has an appropriate level of disease). The following compounds can inhibit at least 80% of grape bacillus : P.13, P.28

Wheat leaf rust (Puccinia recondita f. sp. tritici) / wheat / leaf disc prevention (leaf rust)

The wheat leaf cultivar (cv) Kanzler was placed on a 24-well plate of agar and sprayed with a test compound diluted with water at a rate of 200 ppm. One day after application, the leaf discs were inoculated with a spore suspension of the fungus. The inoculated leaf segments were incubated at 19 ° C and 75% relative humidity in a climate chamber at 12/12 hours (light/dark) illumination, and the activity of the compounds was assessed as a percentage of disease control and untreated Case comparison (when an appropriate disease level occurs in an untreated test leaf segment (7 to 9 days after administration)). The following compounds inhibit wheat leaf rust by at least 80%: P.16, P.15, P.01, P.05, P.02, P.13, P.04, P.12, P.11, P .17, P.18, P.19, P.21, P.22, P.23, P.24, P.25, P.26, P.27, P.28, P.29, P.30 , P.31, P.33, P.34, P.35, P.36, P.37, P.38, P.40, P.42, P.43, P.44, P.45

Wheat leaf rust (Puccinia recondita f. sp. tritici) / wheat / leaf dish treatment (leaf rust)

The wheat leaf cultivar (cv) Kanzler was placed on a 24-well plate of agar. The leaf segments are inoculated with a spore suspension of the fungus. The well plates were stored in the dark at 19 ° C and 75% relative humidity. One day after the inoculation, the formulated test compound was diluted with water and applied at an application rate of 200 ppm. The leaf segments were cultured in a climate chamber at 19 ° C and 75% relative humidity in 12/12 hours (light/dark) illumination, and the activity of the compounds was assessed as a percentage of disease control, with untreated cases. Compared to when an appropriate disease level occurs in an untreated test leaf segment (6 to 8 days after administration). The following compounds inhibit wheat leaf rust by at least 80%: P.16, P.15, P.01, P.05, P.02, P.09, P.13, P.04, P.03, P .12, P.11, P.17, P.18, P.19, P.21, P.22, P.23, P.24, P.25, P.26, P.27, P.28 , P.29, P.30, P.31, P.33, P.34, P.35, P.36, P.37, P.38, P.40, P.42, P.43, P .44, P.45

Phaeosphaeria nodorum ( Septoria nodorum )/Wheat/leaf prevention (wheat spot):

The wheat leaf cultivar Kanzler was placed on a 24-well plate of agar and sprayed with a test compound diluted with water at a rate of 200 ppm. After 2 days of application, the leaf discs were inoculated with a spore suspension of the fungus. The inoculated test leaves were incubated at 20 ° C and 75% relative humidity in a climate chamber at 12/12 hours (light/dark) illumination, and the activity of the compounds was assessed as a percentage of disease control, and Compared to the case of treatment (when an untreated check leaf (5 to 7 days after administration) has an appropriate level of disease). The following compounds can inhibit wheat leaf blight at least 80%: P.16, P.15, P.01, P.05, P.02, P.09, P.13, P.04, P.07, P .03, P.12, P.11, P.17, P.18, P.19, P.20, P.21, P.22, P.23, P.24, P.25, P.26 , P.27, P.28, P.29, P.30, P.31, P.33, P.34, P.35, P.36, P.37, P.38, P.39, P .40, P.41, P.42, P.43, P.44, P.45

Pyrenophora teres / barley / leaf disc prevention (net blotch):

The barley leaf cultivar Hasso was placed on a 24-well plate of agar and sprayed with a test compound diluted with water at a rate of 200 ppm. Two days after the application of the test solution, the leaf segments were inoculated with a spore suspension of the fungus. The inoculated leaf segments were incubated at 20 ° C and 65% relative humidity in a climate chamber at 12/12 hours (light/dark) illumination, while the activity of the compounds was assessed for disease control and untreated The case is compared (when the appropriate disease level occurs in the untreated test leaf segment (5-7 days after application)). The following compounds can inhibit barley pathogens by at least 80%: P.16, P.15, P.01, P.05, P.02, P.09, P.10, P.13, P.07, P .03, P.12, P.11, P.17, P.18, P.19, P.20, P.21, P.22, P.23, P.24, P.25, P.26 , P.27, P.28, P.29, P.30, P.31, P.33, P.34, P.35, P.36, P.37, P.38, P.40, P .42, P.43, P.44, P.45

Focke sclerotiorum Botrytis (Botryotinia fuckeliana) (Botrytis cinerea Botrytis cinerea) / liquid culture (gray mold):

The fungal conidia stored at low temperature are directly mixed into the nutrient medium (Vogels medium). After the DMSO solution of the test compound was placed in a 96-well microplate at a rate of 200 ppm, a nutrient medium containing fungal spores was added. The test plates were incubated at 24 ° C and the growth inhibition was determined photometrically after 3 to 4 days after application. The following compounds can inhibit at least 80% of Botrytis cinerea : P.16, P.15, P.01, P.09, P.10, P.13, P.04, P.07, P.08 , P.03, P.12, P.11, P.21, P.22, P.23, P.24, P.25, P.26, P.27, P.28, P.29, P .30, P.31, P.33, P.34, P.35, P.36, P.37, P.38, P.39, P.40, P.41, P.42, P.43 , P.44, P.45

Original melons anthracnose (Glomerella lagenarium) (formerly Cucumber Anthracnose Colletotrichum lagenarium) / liquid culture (anthrax):

The fungal conidia stored at low temperature are directly mixed into the nutrient medium (PDB potato dextrose broth). After the DMSO solution of the test compound was placed in a 96-well microplate at a rate of 200 ppm, a nutrient medium containing fungal spores was added. The test plates were incubated at 24 ° C and growth inhibition was measured photometrically 3 to 4 days after application. The following compounds can inhibit at least 80% of melon anthrax pathogens : P.16, P.15, P.01, P.05, P.02, P.13, P.07, P.12, P.11, P .17, P.18, P.21, P.22, P.23, P.25, P.26, P.27, P.28, P.29, P.30, P.31, P.35 , P.36, P.37, P.38, P.39, P.40, P.41, P.42, P.43, P.44, P.45

Leptosphaeria peanut (Mycosphaerella arachidis) (peanut brown classes bacteria Cercospora arachidicola) / liquid culture (leaf spot):

The fungal conidia stored at low temperature are directly mixed into the nutrient medium (PDB potato dextrose broth). After the DMSO solution of the test compound was placed in a 96-well microplate at a rate of 200 ppm, a nutrient medium containing fungal spores was added. The test plates were incubated at 24 ° C and the growth inhibition was determined photometrically after 4 to 5 days after application. The following compounds may inhibit groundnut Leptosphaeria at least 80%: P.16, P.15, P.14, P.01 , P.05, P.02, P.09, P.10, P.13, P .04, P.07, P.08, P.03, P.12, P.11, P.17, P.18, P.19, P.20, P.21, P.22, P.23 , P.24, P.25, P.26, P.27, P.28, P.29, P.30, P.31, P.33, P.34, P.35, P.36, P .37, P.38, P.39, P.40, P.41, P.42, P.43, P.44, P.45

Mycosphaerella graminicola ( Septoria tritici ) / liquid culture (spot blight):

The fungal conidia stored at low temperature are directly mixed into the nutrient medium (PDB potato dextrose broth). After the DMSO solution of the test compound was placed in a 96-well microplate at a rate of 200 ppm, a nutrient medium containing fungal spores was added. The test plates were incubated at 24 ° C and the growth inhibition was determined photometrically after 4 to 5 days after application. The following compounds can inhibit at least 80% of wheat leaf spot blight : P.16, P.15, P.14, P.05, P.02, P.09, P.10, P.13, P.07, P.08, P.06, P.03, P.11, P.17, P.18, P.19, P.21, P.22, P.23, P.24, P.25, P. 26. P.27, P.28, P.29, P.30, P.31, P.33, P.34, P.35, P.36, P.37, P.38, P.39, P.40, P.41, P.42, P.43, P.44, P.45

Gaeumannomyces graminis / liquid culture (grain total erosion):

The fungal hyphae fragments stored at low temperature were directly mixed into the nutrient medium (PDB potato dextrose broth). After placing the test compound in DMSO at a rate of 200 ppm into a 96-well microplate, a nutrient medium Cp.33 containing fungal spores was added. The test plates were incubated at 24 ° C and the growth inhibition was determined photometrically after 4 to 5 days after application. The following compounds may inhibit pathogen Gaeumannomyces by at least 80%: P.16, P.15, P.14 , P.05, P.02, P.09, P.10, P.13, P.07, P.08, P.06, P.03, P.11, P.17, P.18, P.19, P.20, P.21, P.22, P.23, P.24, P. 25. P.26, P.28, P.29, P.30, P.31, P.40, P.42, P.43, P.44

Thanatephorus cucumeris ( Rhizoctonia solani ) / liquid culture (root rot, stagnation):

The hyphae of the newly grown fungal liquid culture is directly mixed into the nutrient medium (PDB potato dextrose broth). After the DMSO solution of the test compound was placed in a 96-well microplate at a rate of 200 ppm, a nutrient medium containing the fungal material was added. The test plates were incubated at 24 ° C and the growth inhibition was determined photometrically after 3 to 4 days after application. The following compounds can inhibit at least 80% of cruciferous vegetable seedlings : P.16, P.15, P.01, P.05, P.02, P.04, P.07, P.03, P .12, P.11, P.17, P.24, P.25, P.26, P.27, P.28, P.29, P.30, P.31, P.33, P.34 , P.35, P.36, P.37, P.38, P.39, P.40, P.42, P.43, P.44, P.45

Monographella nivalis ( Microdochium nivale ) / liquid culture (cereal root rot):

The fungal conidia stored at low temperature are directly mixed into the nutrient medium (PDB potato dextrose broth). After the DMSO solution of the test compound was placed in a 96-well microplate at a rate of 200 ppm, a nutrient medium containing fungal spores was added. The test plates were incubated at 24 ° C and the growth inhibition was determined photometrically after 4 to 5 days after application. The following compounds can inhibit at least 80% of wheat leaf blight fungus : P.15, P.01, P.13, P.07, P.12, P.11, P.17, P.18, P.24 , P.25, P.26, P.27, P.28, P.29, P.30, P.31, P.39, P.40, P.41, P.42, P.43, P .44, P.45

Blumeria graminis f. sp. tritici ( Erysiphe graminis f. sp. tritici ) / wheat / leaf disc prevention (wheat powdery mildew):

The wheat leaf cultivar Kanzler was placed on a 24-well plate of agar and sprayed with a test compound diluted with water at a rate of 200 ppm. One day after the application, the plants infected with powdery mildew were shaken on top of the test tray to inoculate the leaf discs. The inoculated leaf discs were incubated at 20 ° C and 60% relative humidity in a climate chamber in a darkness of 24 hours followed by 12/12 hours (dark/light) illumination, and the activity of the compounds was evaluated as a percentage of disease control. And compared to untreated cases (when untreated lesions (6 to 8 days after application) have appropriate disease levels). The following compounds can inhibit wheat powdery mildew by at least 80%: P.16, P.15, P.01, P.05, P.02, P.13, P.04, P.07, P.12, P. 11. P.17, P.18, P.19, P.20, P.21, P.22, P.23, P.24, P.25, P.26, P.27, P.28, P.29, P.30, P.31, P.33, P.34, P.35, P.36, P.37, P.38, P.39, P.40, P.41, P. 42. P.43, P.44, P.45

Alternaria solani / tomato / leaf dish (early blight):

Tomato leaf cultivar (cv.) Baby Seedlings were placed on agar in a multi-well plate (24-well plate) and sprayed with a test compound diluted with water at a rate of 200 ppm. After 2 days of application, the leaf discs were inoculated with a spore suspension of the fungus. The inoculated leaf discs were cultured in a climate chamber at 23 ° C / 21 ° C (day / night) and 80% relative humidity in 12/12 hours (light / dark) illumination, while the activity of the compound was controlled by disease. Evaluate and compare to untreated cases (when untreated check leaves (5-7 days after application) have appropriate disease levels). The following compounds can inhibit at least 80% of tomato early blight : P.12, P.13, P.21, P.22, P.27, P.29, P.42, P.44

Pythium ultimum / liquid culture (seedling disease)

The newly grown fungal liquid cultured hyphal fragments and oospores are directly mixed into the nutrient medium (potato glucose broth). After the DMSO solution of the test compound was placed in a 96-well microplate at a rate of 200 ppm, a nutrient medium containing the fungal hyphae/spore mixture was added. The test discs were cultured at 24 ° C and the growth inhibition was determined photometrically 2 to 3 days after application. The following compounds can inhibit Pythium by at least 80%: P.05, P.13, P.12, P.17, P.18, P.19, P.21, P.25, P.27, P.28 , P.43, P.44, P.45

Claims (21)

a compound of formula (I), Or a salt or N-oxide thereof, wherein R ¹ represents hydrogen, halogen, CN, SH, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfinyl, C ₁ -C _8- alkylsulfonyl, NH ₂ , C ₁ -C ₁₀ alkyl, C ₃ -C ₈ cycloalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl, (R ⁷ O)carbonyl ( C ₁ -C ₄ alkyl), phenyl or pyridyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and pyridyl groups can be independently selected from one or more of the following groups: Alternative substitution: halogen, CN, NH ₂ , NH-C ₁ -C ₈ alkyl, N(C ₁ -C ₈ alkyl) ₂ , NO ₂ , OR ⁷ , C ₁ -C ₄ alkyl, C ₁ - a C ₄ haloalkyl group, a C ₃ -C ₆ cycloalkyl group, and a 5- or 6-membered heterocyclic ring (containing one to three heteroatoms independently selected from O, S and N, provided that the heterocyclic ring does not comprise a phase An adjacent oxygen atom, an adjacent sulfur atom, or an adjacent sulfur and oxygen atom; A ² represents a G-1 ring: D ¹ represents N or CY ¹ ; D ² represents N or CY ² ; wherein neither D ¹ nor D ² can be N; D ³ represents N or CR ⁶ ; D ⁴ represents N or CR ⁵ ; wherein D ³ and D ^{4 are both} Cannot be N; each independently R ² , R ⁴ , R ⁵ and R ⁶ represent hydrogen, halogen, CN, NO ₂ , C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₂ -C ₈ Alkenyl, C ₂ -C ₈ alkynyl, phenyl, 5- or 6-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S and N, provided that the heterocycle does not contain adjacent Oxygen atom, adjacent sulfur atom, or adjacent sulfur and oxygen atom), COR ⁸ , OR ⁷ , SH, C ₁ -C ₈ alkylthio group, C ₁ -C ₈ alkyl sulfinylene group , C ₁ -C ₈ alkylsulfonyl, phenylthio, phenylsulfinylene, phenylsulfonyl, N(R ⁹ ) ₂ , CO ₂ R ⁷ , O(CO)R ⁸ , CON( R ⁹ ) ₂ , NR ⁹ COR ⁸ or CR ⁸ N-OR ⁷ , wherein the alkyl group, the cycloalkyl group, the alkenyl group, the alkynyl group, the phenyl group and the heterocyclic ring may be one or more selected from the group consisting of halogen, CN, NH ₂ , NO ₂ , OR ⁷ , C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl independently selected groups are optionally substituted; or R ⁴ and R ⁵ , R ⁵ and R ² , or R ⁶ and R ² together with the pyridine ring segment connected to it You may be able to form a partially or fully unsaturated 5- to 7-membered carbocyclic ring, or a partially or fully unsaturated 5- to 7-membered heterocyclic ring (containing from one to three O, S, N and N (R ⁹⁾ Independently selected heteroatoms, provided that the heterocyclic ring does not contain adjacent oxygen atoms, adjacent sulfur atoms, or adjacent sulfur and oxygen atoms), and wherein R ⁴ and R ⁵ , R ⁵ and R ² Or a ring formed by R ⁶ and R ² may be derived from one or more of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C _{The 4} alkoxy group and the C ₁ -C ₄ haloalkoxy group are independently selected from the group to be selectively substituted; X represents X-2, X-3, X-4 or X-5: The respective independent Z ¹ , Z ² , Z ³ , Z ⁵ , Z ⁶ , Z ⁷ , Z ⁸ , Z ⁹ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ represent CR ¹⁰ R ¹¹ , C=O or C= CR ¹² R ¹³ ; Z ⁴ and Z ¹² represent CR ¹⁴ R ¹⁵ , SiR ¹⁶ R ¹⁷ , C=O or C=CR ¹² R ¹³ ; or in each case, two adjacent radicals Z ⁴ and Z ⁵ Or Z ⁷ with Z ⁸ or Z ⁸ with Z ⁹ or Z ¹¹ with Z ¹² or Z ¹² with Z ¹³ or Z ¹³ with Z ¹⁴ , possibly together representing from CR ¹⁰ =CR ¹¹ - and -C≡C- Selected groups wherein X-4 or X-5 may not contain more than one such group; each individually independent R ¹⁰ and R ¹¹ represents hydrogen, halogen, CN, OH, C ₁ -C ₄ alkane a C ₁ -C ₄ haloalkyl or phenyl group wherein the phenyl group is derived from one or more of halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ The alkoxy group and the C ₁ -C ₄ haloalkoxy group independently selected are selectively substituted; or R ¹⁰ and R ¹¹ together with the carbon atom to which they are attached may form a C ₃ -C ₆ ring Alkyl or C ₃ -C ₆ halocycloalkyl; each individually independent R ¹² and R ¹³ represent hydrogen, halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl; each individually independent R ^14, R ^15, R ¹⁶ and R ¹⁷ TABLE hydrogen, _{halogen, CN, OH, C 1 -C} 4 alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or phenyl, wherein the phenyl group is one or more selected from halogen, a group independently selected from CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy; Or R ¹⁴ and R ¹⁵ together with the carbon atom to which they are attached may form a C ₃ -C ₆ cycloalkyl group or a C ₃ -C ₆ halocycloalkyl group; wherein the groups X-2, X-3, X- 4 X-5 and contain at most one ring, which comprises only three groups of Z ¹ to Z ¹⁴ in a group, or a group Z ¹ to Z two ^14-yl, or a group Z ¹ to Z ¹⁴ group Or four of the radicals Z ¹ to Z ¹⁴ as ring members; and wherein Z ¹ , Z ³ , Z ⁶ and Z ¹⁰ groups are not substituted by OH; and wherein Z ¹ , Z ² , Z ³ , Z ⁴ , Z ⁵ , Z ⁶ , Z ⁷ , Z ⁸ , Z ⁹ , Z ¹⁰ , Z ¹¹ , Z ¹² , Z ¹³ and Z ¹⁴ none of the carbon atoms substituted by two OH; independent Y ¹ , Y ² and Y ³ represent hydrogen, halogen, CN, NO ₂ , C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl, Phenyl, 5- or 6-membered heterocyclic ring (containing one to From O, S and N heteroatoms independently selected, and the conditions for the heterocyclic ring does not contain adjacent oxygen atoms, adjacent sulfur atom, a sulfur or oxygen atom adjacent ^{to), COR 8, OR 7,} SH , C ₁ -C ₈ alkylthio group, C ₁ -C ₈ alkylsulfinyl group, C ₁ -C ₈ alkylsulfonyl group, phenylthio group, phenylsulfinylene group, phenylsulfonate a group, N(R ⁹ ) ₂ , CO ₂ R ⁷ , O(CO)R ⁸ , CON(R ⁹ ) ₂ , NR ⁹ COR ⁸ or CR ⁸ N-OR ⁷ , wherein alkyl, cycloalkyl, alkenyl , alkynyl, phenyl and heterocyclic ring may be independently selected from one or more of halogen, CN, NH ₂ , NO ₂ , OR ⁷ , C ₁ -C ₄ alkyl and C ₁ -C ₄ haloalkyl Selectively substituted; or Y ¹ and Y ³ or Y ² and Y ³ together with the pyridine ring segment attached thereto, may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring, or a portion Or a fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, N and N(R ⁹ ), provided that the heterocyclic ring does not contain an adjacent oxygen atom, An adjacent sulfur atom, or an adjacent sulfur and oxygen atom), and wherein the ring formed by Y ¹ and Y ³ or Y ² and Y ³ may be a ring Or a plurality of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy The independently selected groups are optionally substituted; A ¹ represents ring A-1, A-2, A-3, A-4, A-5, A-6 or A-7: Individually independent R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ and R ²² represent hydrogen, halogen, CN, NO ₂ , C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₂ -C ₈ olefin a C ₂ -C ₈ alkynyl group, a phenyl group, a 5- or 6-membered heterocyclic ring (containing one to three heteroatoms independently selected from O, S and N, provided that the heterocyclic ring does not contain adjacent Oxygen atom, adjacent sulfur atom, or adjacent sulfur and oxygen atom), benzyl, COR ⁸ , OR ⁷ , SH, C ₁ -C ₈ alkylthio group, C ₁ -C ₈ alkylsulfin Sulfhydryl, C ₁ -C ₈ alkylsulfonyl, phenylthio, phenylsulfinylene, phenylsulfonyl, N(R ⁹ ) ₂ , CO ₂ R ⁷ , O(CO)R ⁸ , CON(R ⁹ ) ₂ , NR ⁹ COR ⁸ or CR ⁸ N-OR ⁷ , wherein alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, heterocyclic and benzyl may be one or more from halogen, CN a group independently selected from NH ₂ , NO ₂ , OR ⁷ , C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, or R ¹⁸ and R ²¹ , R ¹⁸ and R ²² , or R ²⁰ and R ²¹ together with a segment of the ring to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring. Ring One to three heteroatoms independently selected from O, S, N and N(R ⁹ ), provided that the heterocycle does not contain adjacent oxygen atoms, adjacent sulfur atoms, or adjacent sulfur and oxygen atoms) And wherein the ring formed by R ¹⁸ and R ²¹ , R ¹⁸ and R ²² or R ²⁰ and R ²¹ may be derived from one or more of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkane a group independently selected from a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₄ alkoxy group and a C ₁ -C ₄ haloalkoxy group; when A ¹ is A-1 D ¹ is CY ¹ , then R ²² and Y ¹ together with the fragment to which it is attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring, or a partially or fully unsaturated 5- to 7-membered ring. a heterocyclic ring containing one to three heteroatoms independently selected from O, S, N and N(R ⁹ ), provided that the heterocyclic ring does not contain adjacent oxygen atoms, adjacent sulfur atoms, or adjacent Sulfur and oxygen atoms), and wherein the ring formed by R ²² and Y ¹ may be derived from one or more of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ Haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ alkylthio group are independently selected The radicals are optionally substituted; each independently R ⁷ represents hydrogen, C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ Alkynyl, C ₁ -C ₄ alkylsulfonyl, phenyl, benzyl or 5- or 6-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S and N, provided that the hetero The ring does not contain adjacent oxygen atoms, adjacent sulfur atoms, or adjacent sulfur and oxygen atoms), wherein alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and heterocyclic rings are One or more from halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ halo Selective groups selected independently of oxy, C ₁ -C ₄ -alkyl-C ₁ -C ₄ -alkoxy and C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl Substituted; each individually independent R ⁸ represents hydrogen, C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl, phenyl, benzyl Or pyridyl, wherein alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl, pyridyl is derived from one or more of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C _4- alkyl, C ₁ -C ₄ haloalkane a group independently selected from a C ₁ -C ₄ alkoxy group and a C ₁ -C ₄ haloalkoxy group; each individually independent R ⁹ represents hydrogen, OH, C ₁ -C ₈ Alkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl or COR ⁸ , Wherein alkyl, alkoxy, alkenyl and alkynyl are optionally substituted by more than one halogen; wherein when two R ⁹ groups are attached to the same nitrogen atom, these groups may be the same or different Wherein when two R ⁹ groups are attached to the same nitrogen atom, the two groups cannot be OH, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy; and wherein when two R ⁹ When the same nitrogen atom is attached to the same, the two groups together with the nitrogen atom to which they are attached may form rings B-1, B-2, B-3, B-4, B-5, B-6, B-7 or B-8: The ring formed therein is derived from halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C More than one independently selected one of the ₄ haloalkoxy groups is selectively substituted. The compound according to claim 1, wherein: R ¹ represents hydrogen, C ₁ -C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl, C ₃ -C ₈ cycloalkyl, Phenyl, pyridyl or (R ⁷ O)carbonyl (C ₁ -C ₄ alkyl) wherein alkyl, alkenyl, alkynyl, cycloalkyl, phenyl and pyridyl may be derived from one or more from halogen, CN , OR ⁷ , NH ₂ , NH-C ₁ -C ₈ alkyl, N(C ₁ -C ₈ alkyl) ₂ , C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C _a group selected independently of ₆ cycloalkyl and pyridyl groups for selective substitution; D ¹ represents N or CY ¹ ; D ² represents CY ² ; D ³ represents N or CR ⁶ ; D ⁴ represents CR ⁵ ; R ² , R ⁴ , R ⁵ and R ⁶ represent hydrogen, halogen, CN, OR ⁷ , C ₁ -C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₃ -C ₈ cycloalkyl, phenyl, pyridine Base, N(R ⁹ ) ₂ , CO ₂ R ⁷ , NR ⁹ COR ⁸ , SH, C ₁ -C ₈ alkylthio group, C ₁ -C ₈ alkylsulfinyl group, C ₁ -C ₈ alkane Alkylsulfonyl, phenylthio, phenylsulfinyl or phenylsulfonyl, wherein the alkyl, alkenyl, cycloalkyl, phenyl and pyridyl groups may be derived from one or more of halogen, CN, OR ⁷ , C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkoxy Independently selected out of a group to optionally substituted; or R ⁴ and R ^5, R ⁵ and R ^2, or R ² and R ⁶ together with the pyridine ring segment connected to it, may be able to form a partially or fully unsaturated 5 a 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, N and N(R ⁹ ), provided that a heterocyclic ring does not contain an adjacent oxygen atom, an adjacent sulfur atom, or an adjacent sulfur and oxygen atom), and wherein R ⁴ and R ⁵ , R ⁵ and R ² or R ² and R ⁶ are formed. Rings, independently selected from one or more of halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy The resulting group is selectively substituted; X represents X-3 or X-5; each independently Z ³ , Z ⁵ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ represent CR ¹⁰ R ¹¹ or C=CR ¹² R ¹³ ; Z ⁴ and Z ¹² represent CR ¹⁴ R ¹⁵ or C=CR ¹² R ¹³ ; or in each case, two adjacent radicals Z ⁴ and Z ⁵ or Z ¹¹ and Z ¹² or Z ¹² and Z ¹³ or Z ¹³ and Z ^14, may together represent from ¹⁰ = CR ¹¹ -CR - group and the selected -C≡C-, or wherein X-3 X-5 may not contain Through such a group; each individually and independently R ¹¹ R ¹⁰ represents hydrogen, _{halogen, CN, OH, C 1 -C} 4 alkyl or C ₁ -C ₄ haloalkyl; each separate independent R ¹² and R ¹³ represent hydrogen, halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl; each individually independent R ¹⁴ and R ¹⁵ represent hydrogen, halogen, CN, OH, C ₁ -C ₄ An alkyl group, a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₄ alkoxy group or a phenyl group, wherein the phenyl group may be one or more selected from the group consisting of halogen, CN, methyl, halomethyl, methoxy and halo The groups independently selected by the oxy group are optionally substituted, or R ¹⁴ and R ¹⁵ together with the carbon atom to which they are attached may form a C ₃ -C ₆ cycloalkyl group or a C ₃ -C ₆ halocycloalkyl group. And each independently Y ¹ , Y ² and Y ³ represent hydrogen, halogen, CN, OR ⁷ , C ₁ -C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₃ -C ₈ cycloalkyl, phenyl, Pyridyl, N(R ⁹ ) ₂ , CO ₂ R ⁷ , NR ⁹ COR ⁸ , SH, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfinylene, C ₁ -C ₈ Alkylsulfonyl, phenylthio, phenylsulfinylene or phenylsulfonyl, wherein the alkyl, alkenyl, cycloalkyl, phenyl and pyridyl groups may be derived from one or more _{^{Su, CN, OR 7, C 1}} -C 4 alkyl, C ₁ -C ₄ haloalkyl groups independently selected out selectively substituted; A ¹ represents a cycloalkyl A-1, A-2, A-3, A-4, A-5, A-6 or A-7; each independently R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ and R ²² represent hydrogen, halogen, CN, OR ⁷ , C ₁ -C ₈ alkyl , C ₂ -C ₈ alkenyl, C ₃ -C ₈ cycloalkyl, phenyl, pyridyl, benzyl, N(R ⁹ ) ₂ , CO ₂ R ⁷ , NR ⁹ COR ⁸ , SH, CR ⁸ N- OR ⁷ , C ₁ -C ₈ alkylthio group, C ₁ -C ₈ alkylsulfinyl group, C ₁ -C ₈ alkylsulfonyl group, phenylthio group, phenylsulfinylene group or phenyl group A sulfonyl group in which an alkyl group, an alkenyl group, a cycloalkyl group, a phenyl group, a pyridyl group and a benzyl group may be one or more halogen, CN, OR ⁷ , C ₁ -C ₄ alkyl, C ₁ -C ₄ halo The independently selected groups of alkyl groups are optionally substituted; each independently R ⁷ represents hydrogen, C ₁ -C ₈ alkyl, C ₁ -C ₈ haloalkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl, C ₃ -C ₈ haloalkenyl, C ₃ -C ₈ haloalkynyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, phenyl, Benzyl or pyridyl, wherein phenyl, benzyl and pyridyl are composed of one or more halogen, CN a group independently selected from NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy a group optionally substituted; each independently R ⁸ represents hydrogen, C ₁ -C ₈ alkyl or C ₁ -C ₈ haloalkyl; each independently R ⁹ represents hydrogen, C ₁ -C ₈ alkane Or COR ⁸ ; wherein when two R ⁹ groups are attached to the same nitrogen atom, the groups may be the same or different; and wherein when the two R ⁹ groups are attached to the same nitrogen atom, The ring, together with the nitrogen atom to which it is attached, may form a ring B-1, B-2, B-3, B-4 or B-5, wherein the ring formed may be composed of one or more halogen, methyl and The groups independently selected from the halomethyl group are selectively substituted. The compound according to claim 1, wherein: R ¹ represents hydrogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, phenyl or pyridyl, wherein alkyl, alkenyl, phenyl and pyridine The group may be one or more from halogen, CN, OH, NH ₂ , NH-C ₁ -C ₄ alkyl, N(C ₁ -C ₄ alkyl) ₂ , C ₁ -C ₄ alkyl, C ₁ -C _a group selected independently of ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy and C ₃ -C ₆ cycloalkyl; D ¹ represents N or CY ¹ ; D ² represents CY ² ; D ³ represents N or CR ⁶ ; D ⁴ represents CR ⁵ ; each independently R ² , R ⁴ , R ⁵ and R ⁶ represent hydrogen, halogen, OR ⁷ , CN, C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, N (R ⁹⁾ _2, phenyl, CO ₂ R ⁷ or NR ⁹ COR ^8, wherein the alkyl, cycloalkyl and phenyl group by one or more halo from , CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy independently selected groups are optionally substituted; or R ⁴ and R ⁵ , R ⁵ and R ² , or R ² and R ⁶ together with the pyridyl ring segment to which they are attached may form a fully or partially unsaturated 5- or 6-membered carbocyclic ring, and Can be one Or a plurality of groups independently selected from a halogen, a methyl group and a halomethyl group to be selectively substituted; X represents X-3; and each independently Z ³ and Z ⁵ represents CR ¹⁰ R ¹¹ or C=CR ¹² R ¹³ ; Z ⁴ represents CR ¹⁴ R ¹⁵ or C=CR ¹² R ¹³ ; or Z ⁴ together with Z ⁵ represents a group selected from -CR ¹⁰ =CR ¹¹ - and -C≡C-; each individually independent R ¹⁰ and R ¹¹ represent hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl; each individually independent R ¹² and R ¹³ represent hydrogen, halogen, C ₁ - C ₄ alkyl, C ₁ -C ₄ haloalkyl; each individually independent R ¹⁴ and R ¹⁵ represents hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl or phenyl, wherein phenyl is optionally selected from one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy. Substituting; or R ¹⁴ and R ¹⁵ together with the carbon atom to which they are attached may form a C ₃ -C ₆ cycloalkyl group or a C ₃ -C ₆ halocycloalkyl group; wherein Z ³ , Z ⁴ and Z ^{5 are} among only the at least two substituents consisting of hydrogen, or Z ⁴ together represent the Z ⁵ -C≡C-; each independently of Y ^1, Y ² and Y ³ represents hydrogen, halogen _{^{, OR 7, CN, C 1}} -C 4 alkyl, C ₃ -C ₆ cycloalkyl, N (R ⁹⁾ _2, phenyl, CO ₂ R ⁷ or NR ⁹ COR ^8, wherein the alkyl, cycloalkyl, And the phenyl group may be independently selected from one or more of halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy The resulting group is optionally substituted; A ¹ represents ring A-1, A-2 or A-4; each independently R ¹⁸ , R ²⁰ , R ²¹ and R ²² represent hydrogen, halogen, OR ⁷ , CN, C _1- C ₄ alkyl, C ₃ -C ₆ cycloalkyl, N(R ⁹ ) ₂ , C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C _4- alkylsulfonyl, phenyl, benzyl, CO ₂ R ⁷ , CR ⁸ N-OR ⁷ or NR ⁹ COR ⁸ , wherein alkyl, cycloalkyl, phenyl and benzyl may be one or more halogen a group independently selected from CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy; Each of the respective independent R ⁷ represents hydrogen, C ₁ -C ₈ alkyl, C ₁ -C ₈ haloalkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ haloalkenyl, C ₃ -C ₈ alkyne , C ₃ -C ₈ haloalkynyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, benzene a benzyl, benzyl or pyridyl group, wherein the phenyl, benzyl and pyridyl groups are derived from one or more of halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ The alkoxy group is optionally substituted with a group independently selected from a C ₁ -C ₄ haloalkoxy group; each independently R ⁸ represents hydrogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ halo An alkyl group; each independently R ⁹ represents hydrogen or a C ₁ -C ₄ alkyl group; wherein when two R ⁹ groups are attached to the same nitrogen atom, these groups may be the same or different; When two R ⁹ groups are attached to the same nitrogen atom, the two groups, together with the nitrogen atom to which they are attached, may form a ring B-1, B-2, B-3, B-4 or B-5. The ring formed therein may be selectively substituted by one or more groups independently selected from a halogen, a methyl group and a halomethyl group. The compound according to claim 1, wherein: R ¹ represents hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, phenyl or pyridin-2-yl, wherein phenyl and pyridine-2 The group may be optionally substituted by one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy; D ¹ represents CY ¹ ; D ² represents CY ² D ³ represents CR ⁶ ; D ⁴ represents CR ⁵ ; each independently R ² , R ⁴ , R ⁵ and R ⁶ represent hydrogen, halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkane Oxyl, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ cycloalkyl, N(R ⁹ ) ₂ , phenyl or CO ₂ R ⁷ wherein alkyl, alkoxy, alkenyloxy, cycloalkane The phenyl group and the phenyl group may be one or more selected from the group consisting of halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy Individually selected groups for selective substitution; or R ⁴ and R ⁵ , R ⁵ and R ² , or R ² and R ⁶ together with the pyridyl ring segment to which they are attached may form complete or partial a saturated 6-membered carbocyclic ring and may be selected from one or more groups independently selected from the group consisting of halogen, methyl and halomethyl. Substituted; X-Representative X-3; each independently Z ³ and Z ⁵ Representative CR ¹⁰ R ¹¹ or ^{C = CR 12 R 13; Z} 4 Representative CR ¹⁴ R ¹⁵ or C = CR ¹² R ^13; or Z ⁴ and Z ⁵ together represent a group selected from -CR ¹⁰ =CR ¹¹ - and -C≡C-; each individually independent R ¹⁰ and R ¹¹ represents hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl Or C ₁ -C ₄ haloalkyl; each individually independent R ¹² and R ¹³ represents hydrogen, halogen, methyl or halomethyl; each individually independent R ¹⁴ and R ¹⁵ represent hydrogen, halogen, CN, OH a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₄ alkoxy group or a phenyl group, wherein the phenyl group may be one or more selected from the group consisting of halogen, CN, methyl, halomethyl, a group independently selected from a methoxy group and a halomethoxy group; or R ¹⁴ and R ¹⁵ together with a carbon atom to which they are attached may form a C ₃ -C ₆ cycloalkyl group or a C ₃ - C ₆ halocycloalkyl; wherein at least two of Z ³ , Z ⁴ and Z ⁵ can only be substituted by hydrogen, or Z ⁴ together with Z ⁵ represent -C≡C-; each independently Y ¹ , Y ² And Y ³ represents hydrogen, halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ cycloalkyl, N(R ⁹ ) ₂ , phenyl or CO ₂ R ⁷ wherein alkyl, alkoxy, alkenyloxy, cycloalkyl and phenyl may be derived from one or more halogen, CN, C ₁ -C ₄ alkyl a group independently selected by a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₄ alkoxy group, or a C ₁ -C ₄ haloalkoxy group; A ¹ represents a ring A-1, A- 2 or A-4; each independently R ¹⁸ , R ²⁰ , R ²¹ and R ²² represent hydrogen, halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ cycloalkyl, N(R ⁹ ) ₂ , C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkane Alkylsulfonyl, phenyl, phenoxy, benzyl, benzyloxy, CR ⁸ N-OR ⁷ or CO ₂ R ⁷ wherein alkyl, alkoxy, alkenyloxy, cycloalkyl, phenyl and The benzyl group can be independently selected from one or more of halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy. The resulting group is optionally substituted; each independently R ⁷ represents hydrogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl; each independently R ⁹ represents hydrogen or C ₁ -C ₄ alkyl; wherein when two R ⁹ groups connected to the same nitrogen atom These groups may be the same or different; and wherein when two R ⁹ groups connected to the same nitrogen atom, two groups, together with the nitrogen atom to which they are connected, may form a ring, B-1, B -2, B-3, B-4 or B-5 wherein the ring formed is optionally substituted by one or more groups independently selected from the group consisting of halogen, methyl and halomethyl. A compound according to claim 1 wherein R ¹ represents a pyridyl group and may be derived from one or more of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl a group optionally substituted with a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ haloalkoxy group, a C ₃ -C ₆ cycloalkyl group and a 5- or 6-membered heterocyclic ring, which is optionally substituted The heterocycle contains from one to three heteroatoms independently selected from O, S and N, provided that the heterocycle does not contain adjacent oxygen atoms, adjacent sulfur atoms, or adjacent sulfur and oxygen atoms. A compound according to the first aspect of the invention, wherein A ² and R ¹ represent pyridin-2-yl, which may be derived from one or more of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C a group independently selected from ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₃ -C ₆ cycloalkyl and 5- or 6-membered heterocyclic ring Alternatively, the heterocyclic ring contains one to three heteroatoms independently selected from O, S and N, provided that the heterocyclic ring does not contain adjacent oxygen atoms, adjacent sulfur atoms, or adjacent sulfur With oxygen atoms. The compound according to any one of claims 1 to 3, wherein R ¹ represents C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, phenyl or pyridyl, wherein alkyl, alkenyl, benzene The group and the pyridyl group may be optionally substituted by one or more groups independently selected from a halogen, a CN, a C ₁ -C ₄ alkoxy group and a C ₁ -C ₄ haloalkoxy group. A compound according to claim 1 wherein D ¹ represents CY ¹ and D ² represents CY ² . The compound according to claim 1, wherein each independently R ² , R ⁴ , R ⁵ and R ⁶ represent hydrogen, C ₁ -C ₄ alkyl, CN or C ₁ -C ₄ alkoxy, wherein alkyl The alkoxy group may be optionally substituted with one or more groups independently selected from halogen, CN, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy. A compound according to claim 1 wherein X represents X-3 or X-5. A compound according to claim 1 wherein X represents X-3. A compound according to claim 1 wherein X represents X-3; Z ³ and Z ⁵ represent a methylene group; Z ⁴ represents CR ¹⁴ R ¹⁵ or C=CR ¹² R ¹³ ; each individually independent R ¹² And R ¹³ represents hydrogen, halogen, methyl or halomethyl; each individually independent R ¹⁴ and R ¹⁵ represents hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl a C ₁ -C ₄ alkoxy group or a phenyl group, wherein the phenyl group may be selected from one or more groups independently selected from halogen, CN, methyl, halomethyl, methoxy and halomethoxy. Sexual substitution; or R ¹⁴ and R ¹⁵ together with the carbon atom to which they are attached may form a C ₃ -C ₆ cycloalkyl group which is optionally substituted by a halogen. The compound according to claim 1, wherein each of the independent Y ¹ and Y ² represents hydrogen, halogen, C ₁ -C ₄ alkyl, CN or C ₁ -C ₄ alkoxy, wherein alkyl and alkoxy It may be optionally substituted by one or more groups independently selected from halogen, CN, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy. The compound according to claim 1, wherein each of the independent Y ¹ , Y ² and Y ³ represents hydrogen, halogen, C ₁ -C ₄ alkyl, CN or C ₁ -C ₄ alkoxy, wherein alkyl and The alkoxy group may be optionally substituted by one or more groups independently selected from halogen, CN, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy. According to the compound of claim 1, A ¹ represents A-1, A-2 or A-4. According to the compound of claim 1, A represents A-1 or A-2. According to the compound of claim 1, wherein when A ¹ is A-1 and D ¹ is CY ¹ , then R ²² and Y ¹ together with the fragment to which it is attached may form partial or complete unsaturated 5- to a 7-membered carbocyclic ring, or a partially or fully unsaturated 5- to 7-membered heterocyclic ring (containing one to three heteroatoms independently selected from O, S, N and N(R ⁹ ), provided that the heterocyclic ring Does not contain adjacent oxygen atoms, adjacent sulfur atoms, or adjacent sulfur and oxygen atoms), and the ring formed by R ²² and Y ¹ may be composed of one or more halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ alkyl sulfide The groups independently selected by Dai Kei are selectively replaced. a compound of formula (VII) Or a salt thereof or an N-oxide; wherein R ²⁸ is a halogen; A ² , R ¹ , X, D ¹ , D ² and Y ³ are as defined in the chemical formula of any one of claims 1 to 17 of the patent application. a compound of (I); or a compound of formula (IX) Or a salt thereof or an N-oxide; wherein A ² , R ¹ , X, D ¹ , D ² and Y ³ are as defined in the compound of the formula (I) of any one of claims 1 to 17; Or a compound of formula (X) Or a salt thereof or an N-oxide; wherein A ² , R ¹ , X, D ¹ , D ² and Y ³ are as defined in the compound of formula (I) of any one of claims 1 to 17; Or a compound of formula (XI) Or a salt thereof or an N-oxide; wherein A ² , R ¹ , X, D ¹ , D ² and Y ³ are as defined in the compound of the formula (I) of any one of claims 1 to 17; Or a compound of formula (XIII) Or a salt thereof or an N-oxide; wherein A ² , R ¹ , X, D ¹ , D ² , Y ³ and R ¹⁸ are as defined in the formula (I) of any one of claims 1 to 17 of the patent application. a compound; or a compound of formula (XIV) Or a salt thereof or an N-oxide; wherein A ² , R ¹ , X, D ¹ , D ² , Y ³ and R ¹⁸ are as defined in the formula (I) of any one of claims 1 to 17 of the patent application. Compound. A compound of the compound (VII) according to claim 18, wherein R ²⁸ represents chlorine, bromine or iodine. A fungicidal composition comprising a fungicidally effective amount of a compound of formula (I) as defined in any one of claims 1 to 17 and optionally comprising at least one additional active ingredient. A method for controlling or preventing a phytopathogenic disease of a practical plant or a propagation material thereof, comprising applying a fungicidally effective amount of a compound of formula (I) to a practical plant, a locus thereof or a propagation material thereof, as claimed in claim 1 As defined in any of the 17 items.