TW201326152A - Novel microbiocides - Google Patents

Abstract

The present invention relates to methods of controlling or preventing phytopathogenic diseases on useful plants or on propagation material thereof comprising applying to useful plants, the locus thereof or propagation material thereof a compound of formula (I) wherein Q, Q', L1, L2, L3, L4, L5, L6 and X are as defined in claim 1. The invention also relates to novel compounds that may be used in said methods, as well as intermediates useful for the preparation of the novel compounds.

Description

Novel microbicide

The present invention relates to novel heterocyclic compounds having microbicidal activity, particularly fungicidal activity. It further relates to intermediates used in the preparation of such compounds, to compositions comprising such compounds and to microorganisms (preferably fungi) which are used in agriculture or horticulture to control or prevent plants from being phytopathogenic (preferably fungi) ) the use of the infection.

2-(pyridin-2-yl)pyrimidines having fungicidal activity are described in WO 2007/116079. The disclosed compounds are characterized by a condensed aliphatic carbocyclic or heterocyclic ring. Surprisingly, it has been found that some heterocyclic systems, including novel compounds, have microbicidal activity.

The present invention relates to a method comprising applying a compound of formula (I) to a useful plant, a locus thereof or a propagation material thereof Wherein L ¹ is N or CD ¹ ; L ² is N or CD ² ; L ³ is N or CD ³ ; L ⁴ is N or CD ⁴ ; L ⁵ is N or CD ⁵ ; L ⁶ is N or CD ⁶ ; ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other 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 comprise Adjacent oxygen atoms, adjacent sulfur atoms or adjacent sulfur and oxygen atoms), COR ¹ , OR ² , SH, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfinylene, C ₁ - C ₈ alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, N(R ³ ) ₂ , CO ₂ R ² , O(CO)R ¹ , CON(R ³ ) ₂ And NR ³ COR ¹ , CR ¹ N-OR ² , wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and heterocyclic ring are optionally independently selected from halogen, CN, by one or more Substituents of NH ₂ , NO ₂ , OR ² , C ₁ -C ₄ alkyl and C ₁ -C ₄ haloalkyl.

Or D ¹ and D ⁵ , D ² and D ⁵ , D ³ and D ⁶ , or D ⁴ and D ⁶ independently of each other together with the fragment to which they are attached may form a partially or fully unsaturated 5- to 7- a 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 ³ ) (conditions are: the heterocyclic ring Does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms), and wherein the ring formed by D ¹ and D ⁵ , D ² and D ⁵ , D ³ and D ⁶ , or D ⁴ and D ⁶ Optionally, one or more independently 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, and Substituted by a C ₁ -C ₄ haloalkoxy group; X represents X-2, X-3, X-4 or X-5:

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 independently of each other represent CR ⁴ R ⁵ , C=O or C= CR ⁶ R ⁷ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ , SiR ¹⁰ R ¹¹ , C=O or C=CR ⁶ R ⁷ ; wherein the combinations X-2, X-3, X-4 and X- 5 contain at most one ring, which comprises only Z ¹ to Z ¹⁴ group comprises one or two Z ¹ to Z ¹⁴ radicals comprising three or Z ¹ to Z ¹⁴ or a group Z ¹ comprises Four of the Z ¹⁴ groups are ring members; 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 N, Z ¹³ and Z ¹⁴ do not represent a carbon atom substituted via two OH groups.

The Q system is selected from the group consisting of Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, and Q-9.

Y ¹ , Y ² , Y ³ and Y ⁴ each independently represent hydrogen, halogen, CN, NO ₂ , C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₂ -C ₈ alkenyl, a C ₂ -C ₈ alkynyl group, a benzyl group, a phenyl group, a 5- or 6-membered heterocyclic ring containing one to three hetero atoms independently selected from O, S and N (provided that the heterocyclic ring does not contain a contiguous Oxygen atom, adjacent sulfur atom or adjacent sulfur and oxygen atom), COR ¹ , OR ² , SH, C ₁ -C ₈ alkylthio group, C ₁ -C ₈ alkylsulfinyl group, C ₁ -C _8- alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, N(R ³ ) ₂ , CO ₂ R ² , O(CO)R ¹ , CON(R ³ ) ₂ , NR ³ COR ¹ , CR ¹ N-OR ² , wherein the alkyl, cycloalkyl, alkenyl, alkynyl, benzyl, phenyl, and heterocyclic ring are optionally independently selected from halogen, by one or more Group substitution of CN, NH ₂ , NO ₂ , OR ² , C ₁ -C ₄ alkyl and C ₁ -C ₄ haloalkyl; when Q systems Q-1, Q-2, Q-3, Q-4, When Q-6 or Q-7, Y ¹ and Y ² , Y ² and Y ³ , or Y ³ and Y ⁴ independently of each other together with the fragment to which they are attached may form a partial or complete unsaturated 5- to 7-membered carbon ring or partially or completely a 5- to 7-membered heterocyclic ring containing from one to three heteroatoms independently selected from O, S, N and N(R ³ ) (provided that the heterocyclic ring does not contain contiguous oxygen atoms, abutting a sulfur atom or an adjacent sulfur and oxygen atom), and wherein the ring formed by Y ¹ and Y ² , Y ² and Y ³ , or Y ³ and Y ⁴ may be optionally independently selected from halogen by one or more , 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 a group substituted with an alkylthio group; when the Q system is Q-1, Q-3, Q-4, Q-7 or Q-8 and the L ¹ is CD ¹ , then Y ¹ and D ¹ are attached thereto along with The above fragment may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated heteroatom containing one or two independently selected from O, S, N and N(R ³ ). a 5- to 7-membered heterocyclic ring (provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms), and wherein the ring formed by D ¹ and Y ¹ is acceptable Optionally selected from one or more of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl a group substituted with a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ haloalkoxy group, and a C ₁ -C ₄ alkylthio group; when the Q system is Q-9 and the L ¹ is CD ¹ , then R ¹² is D ¹ may together be -(G ¹ ) _p -G ² -G ³ -; Q' is selected from the group consisting of Q-1', Q-2', Q-3', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9'

Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently 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, benzyl, phenyl, 5- or 6-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S and N (conditions are: heterozygous The ring does not contain adjacent oxygen atoms, adjacent sulfur atoms or adjacent sulfur and oxygen atoms), COR ¹ , OR ² , SH, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfinylene, C ₁ -C ₈ alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, N(R ³ ) ₂ , CO ₂ R ² , O(CO)R ¹ , CON(R ³ ) ₂ , NR ³ COR ¹ , CR ¹ N-OR ² , wherein the alkyl, cycloalkyl, alkenyl, alkynyl, benzyl, phenyl and heterocyclic ring may optionally be independently or in one or more a group substituted with halogen, CN, NH ₂ , NO ₂ , OR ² , C ₁ -C ₄ alkyl, and C ₁ -C ₄ haloalkyl; when Q' is Q-1', Q-3', Q -2', Q-4', Q-6' or Q-7', Y ^{1 '} and Y ^2' , Y ^2' and Y ^3' , or Y ^3' and Y ^4' are independently of each other The fragment attached thereto can form a partially or fully unsaturated 5- to 7-membered carbocyclic ring. Partially or fully unsaturated, containing from one to three substituents independently selected from 5- to 7-membered heterocyclic ring O, S, N and N (R ³⁾ hetero atom (with the proviso lines: the heterocyclic ring does not contain adjacent oxygen An atom, an adjacent sulfur atom or an adjacent sulfur and oxygen atom), and wherein a ring formed by Y ^{1 '} and Y ^{2 '} , Y ^{2 '} and Y ^{3 '} , or Y ^{3 '} and Y ^{4 '} may optionally be One or more independently 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, C ₁ -C ₄ Substituted with haloalkoxy and C ₁ -C ₄ alkylthio; when Q' is Q-1', Q-3', Q-4', Q-7' or Q-8' and L ⁴ is CD ^{At 4} o'clock, then Y ^{1 '} and D ⁴ together with the fragments to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or partially or fully unsaturated, including one or two independently a 5- to 7-membered heterocyclic ring selected from the heteroatoms of O, S, N and N(R ³ ) (provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen Atom), and wherein the ring formed by D ⁴ and Y ^{1 '} can be optionally independently selected from halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C via one or more Substituted by a group of ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ alkylthio; when Q' is Q-9 'And L ⁴ is CD ⁴ , then R ^{12 '} and D ⁴ may together be -(G ¹ ) _p -G ² -G ³ -; each G ¹ and G ² independently of each other represents -C(R ¹⁴ R ¹⁵ )-; each G ³ independently of each other represents -C(R ¹⁴ R ¹⁵ )-, O, N(R ¹⁶ ) or S; or each combination G ¹ and G ² , or G ² and G ³ , or G ¹ and G ¹ together represent each other independently -CR ¹⁴ =CR ¹⁵ -; each p independently of each other represents 0, 1 or 2; each R ¹ independently of ^one another 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 the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl And benzyl and pyridyl are optionally independently selected from halo, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ - Substituted by a C ₄ alkoxy group and a C ₁ -C ₄ haloalkoxy group; each R ² independently of one another represents hydrogen, C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl, phenyl, benzyl or containing one to a 5- or 6-membered heterocyclic ring independently selected from the heteroatoms of O, S and N (provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms) Wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and heterocyclic ring are optionally independently selected from halo, CN, NH ₂ , NO ₂ , OH, C via one or more _1- C ₄ alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ -alkoxy-C ₁ -C ₄ - Substituted by a group of alkyl groups; each R ³ independently of one another represents hydrogen, OH, C ₁ -C ₈ alkyl, C ₁ -C ₈ alkoxy, C ₁ -C ₈ -alkoxy-C ₁ -C _{a 4} -alkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl or COR ¹ wherein the alkyl, alkoxy, alkenyl and alkynyl groups are optionally substituted by one or more halogens; Wherein when two groups R ³ are attached to the same nitrogen atom, the groups may be the same or different; wherein when the two groups R ³ are attached to the same nitrogen atom, the two groups The group may not be OH, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy; and wherein when two groups R ³ are attached to the same In the case of a 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:

Wherein the ring formed may optionally be selected from one or more independently 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 Alkyla and a C ₁ -C ₄ haloalkoxy group are substituted; R ⁴ and R ⁵ each independently represent hydrogen, halogen, CN, OH, SH, CHO, C ₁ -C ₆ alkyl, C ₂ - C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ alkynyloxy, C ₁ -C ₆ alkylthio, C _1- C ₆ alkoxycarbonyl, C ₃ -C ₆ cycloalkyl, CON(R ³ ) ₂ , NH ₂ , NR ³ COR ¹ , CR ¹ N-OR ² , phenyl or one to four independently selected a 5- or 6-membered heterocyclic ring of a hetero atom of O, S and N (provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms), wherein the alkyl group And an alkenyl group, an alkynyl group, a phenyl group, and a heterocyclic ring, optionally, one or more independently selected from the group consisting of halogen, OH, OR ² , CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, CON(R ³ ) ₂ , NH ₂ , NR ³ COR ¹ And the base of the phenyl group Substituted; or R ⁴ and R ⁵ together with the carbon atoms they are attached to form thereon a C ₃ -C ₆ cycloalkyl group or halogenated C ₃ -C ₆ cycloalkyl group together; each R ⁶ and R ⁷ independently of each other represents hydrogen, halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl; R ⁸ and R ⁹ each independently represent hydrogen, halogen, CN, OH, SH, CHO, C ₁ - C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ alkynyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkoxycarbonyl, C ₃ -C ₆ cycloalkyl, CON(R ³ ) ₂ , NH ₂ , NR ³ COR ¹ , CR ¹ N-OR ² , phenyl Or a 5- or 6-membered heterocyclic ring containing one to four heteroatoms independently selected from O, S and N (provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and An oxygen atom), wherein the alkyl, alkenyl, alkynyl, phenyl and heterocyclic ring are optionally independently selected from one or more of halogen, OH, OR ² , CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, CON(R ³ ) ₂ , NH ₂ , N R ³ COR ¹ and a group of a phenyl group; or R ⁸ and R ⁹ together with the carbon atom to which they are attached form a C ₃ -C ₆ cycloalkyl group or a C ₃ -C ₆ halocycloalkane a radical; R ¹⁰ and R ¹¹ each independently represent hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₂ -C ₄ alkenyl or phenyl, wherein phenyl is optionally substituted with one or more groups independently selected from halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ Substituted by a haloalkyl group, a C ₁ -C ₄ alkoxy group, and a C ₁ -C ₄ haloalkoxy group; R ¹² and R ^{12 '} independently of each other represent hydrogen, halogen, CN, SH, C ₁ -C ₈ alkane sulfur , 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 ² O)carbonyl (C ₁ -C ₄ alkyl), phenyl or pyridyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl And the pyridyl group may be optionally selected from one or more independently selected from the group consisting of halogen, CN, NH ₂ , NH-C ₁ -C ₈ alkyl, N(C ₁ -C ₈ alkyl) ₂ , NO ₂ , OR ² , C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl Group, C ₃ -C ₆ cycloalkyl group and containing one to three independently selected from 5- or 6-membered heterocyclic ring (with the proviso lines O, S and N, heteroatoms: oxygen atom of the heterocyclic ring does not contain adjacent Substituted by a group of adjacent sulfur atoms or adjacent sulfur and oxygen atoms; R ¹³ and R ^13' independently of each other represent hydrogen, C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C3-C ₈ alkenyl, C ₃ -C ₈ alkynyl, phenyl, benzyl or pyridyl group, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and pyridyl optionally substituted with one Or a plurality of independently 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, and C ₁ -C ₄ haloalkane Substituted by a group of oxy; R ¹⁴ and R ¹⁵ each independently represent hydrogen, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ -haloalkoxy; each R ¹⁶ independently of one another represents hydrogen, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₆ cycloalkyl, C ₁ -C ₈ alkyl a carbonyl group or a C ₁ -C ₈ haloalkylcarbonyl group; or a salt or N oxide thereof.

The invention encompasses all agronomically acceptable salts, isomers, structural isomers, stereoisomers, diastereomers, enantiomers, tautomers, and hinders of those compounds. Isomers (atropisomer) and N-oxides. The compounds of formula I can exist in different geometric or optical isomeric forms or in different tautomeric forms. One or more chiral centers may be present, in which case the compound of formula I may be a pure enantiomer, a mixture of enantiomers, a pure diastereomer or a non-pair A mixture of the isomers is present. 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 can be multiple centers of tautomerization. The present invention encompasses all such isomers as well as tautomers and mixtures thereof in all ratios, along with isotopic forms, such as deuterated compounds. Due to the limited rotation around a single bond, there may also be rotational enantiomerism.

Preferably, the method is a method of controlling or preventing a disease caused by a plant pathogen on a useful plant or on a propagation material thereof, and more preferably a control or prevention is present A method of using a disease caused by a phytopathogenic fungus on a plant or on a propagation material thereof.

Halogen (as a separate substituent or in combination with an additional substituent (e.g., haloalkyl)) is generally fluorine, chlorine, bromine or iodine, and is typically fluorine, chlorine or bromine.

Each alkyl moiety (including an alkyl moiety of an alkoxy group, an alkylthio group, etc.) is linear or branched, and is, for example, a methyl group, an ethyl group, a n-propyl group depending on the number of carbon atoms it contains. , n-butyl, n-pentyl, n-hexyl, isopropyl, secondary butyl, isobutyl, tert-butyl, neopentyl, n-heptyl or 1,3-dimethylbutyl, and usually It is a methyl or ethyl group.

The alkenyl group is an unsaturated straight or branched chain having at least one carbon-carbon double bond, and depending on the number of carbon atoms it contains, such as vinyl, 1-propenyl, 2-propenyl, 1-methyl- Vinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl , 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl 1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butene Base, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexyl Alkenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl 2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentene Base, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3- Pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2- Butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3- Dimethyl-3-butenyl, and usually 2-propenyl, 1-methyl-2-propenyl, 2-butenyl, 2-methyl-2-propene base.

The alkynyl group is an unsaturated straight or branched chain having at least one carbon-carbon triple bond, and depending on the number of carbon atoms it contains, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butyl Alkynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 3-methyl-1-butynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl 2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 3 -methyl-1-pentynyl, 4-methyl-1-pentynyl, 1-methyl-2-pentynyl, 4-methyl-2-pentynyl, 1-methyl-3- Pentynyl, 2-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 3, 3,-Dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1,1-dimethyl-2-butynyl, 1-ethyl-3-butynyl, 2 -ethyl-3-butynyl, 1,1-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1,2-dimethyl-3-butyne base.

The haloalkyl moiety is an alkyl moiety substituted with one or more of the same or different halogen atoms and is, for example, monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, dichloromethyl, tri Chloromethyl, 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, and typical The ground is trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl, and dichlorofluoromethyl.

Alkenyloxy, such as methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, di-butoxy and tert-butoxy, and usually methoxy Base or ethoxy group.

Haloalkoxy, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2 -fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy, and usually difluoromethoxy, 2-chloroethoxy And trifluoro Methoxy.

An alkylthio group such as methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, dibutylthio or tert-butylthio, and usually methylsulfide Base or ethylthio group.

Alkylsulfonyl, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, secondary A sulfenyl group or a tertiary butyl sulfonyl group, and is usually a methylsulfonyl or ethylsulfonyl group.

Alkylsulfinyl, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutyl Sulfosyl, secondary butyl sulfinylene or tertiary butyl sulfinylene, and usually methylsulfinyl or ethylsulfinyl.

Alkoxyalkyl, such as methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxy Methyl or isopropoxyethyl.

The cycloalkyl group may be saturated or partially unsaturated, preferably fully saturated, and is, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group.

The aryl group includes a phenyl group, a naphthyl group, an anthracyl group, an anthracenyl group, and an indanyl group, but is usually a phenyl group.

Carbocycles include cycloalkyl groups as well as aryl groups.

A heterocycloalkyl group is a non-aromatic ring which may be saturated or partially unsaturated (preferably fully saturated), comprises a carbon atom as a ring member and at least one hetero atom selected from O, S and N as a ring member. . Examples include oxiranyl, propylene oxide, tetrahydrofuranyl, tetrahydropyranyl, 1,3-dioxolanyl, 1,4-di Dioxanyl, aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, 吖 Oxazinanyl, dioxolane, dithiolan, Olinyl, thio Lolinyl, imidazolidinyl, pyrazolidine and piperazine Base, preferably Lolinyl, pyrrolidinyl, piperidinyl and piperidine More preferably, dioxolane, dithiolan, A phenyl group and a pyrrolidinyl group.

Heteroaryl groups are, for example, monovalent monocyclic or bicyclic aromatic hydrocarbon groups. Examples of monocyclic groups include pyridyl, fluorene Base, pyrimidinyl, pyridyl Base, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furyl, phenylthio, Azolyl, different Azolyl, A oxazolyl group, a thiazolyl group, an isothiazolyl group, and a thiadiazolyl group. Examples of bicyclic groups include quinolyl, hydrazine Base A phenyl group, a benzimidazolyl group, a benzophenylthio group, and a benzothiadiazolyl group. The monocyclic heteroaryl group is preferably a pyridyl group, a pyrrolyl group, an imidazolyl group and a triazolyl group, for example, a 1,2,4triazolyl group, a pyridyl group and an imidazolyl group are preferred.

The terms "heterocycle" and "heterocyclic ring" are used interchangeably and are defined to include heterocycloalkyl as well as heterocyclic aryl groups. Any reference herein to a heterocyclic or heterocyclic ring refers to a specific example given by the definition of heteroaryl and heterocycloalkyl above, and preferably Lolinyl, pyrrolidinyl, piperidinyl, piperidine More preferably, pyridyl, pyrrolyl, imidazolyl and triazolyl (e.g. 1,2,4 triazolyl), more preferably A phenyl group, a pyrrolidinyl group, a pyridyl group, and an imidazolyl group. No heterocycle contains contiguous oxygen atoms, contiguous sulfur atoms or contiguous oxygen and sulfur atoms.

When a moiety is indicated as being (optionally) substituted by, for example, an alkyl group, this includes those moieties in which they are part of a larger group, such as an alkyl group in an alkylthio group and an alkoxy group. The alkyl group in the group, and so on. The same applies to the phenyl moiety in the phenylthio group or the like. When a moiety is indicated as being optionally substituted with one or more other groups, it is preferred that one to five optional substituents are present, more preferably one to three optional substituents. When a part When substituted by a cyclic group (e.g., aryl, heteroaryl, cycloalkyl), it is preferred to have no more than two such substituents, more preferably no more than one such substituent.

The following substituent definitions, including preferred definitions, may be combined in any combination: D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other 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, containing one to four heteroatoms independently selected from O, S and N a 5- or 6-membered heterocyclic ring (conditions such that the heterocyclic ring does not contain an adjacent oxygen atom, an adjacent sulfur atom or an adjacent sulfur or oxygen), COR ¹ , OR ² , SH, C ₁ -C ₈ alkane sulfur , C ₁ -C ₈ alkylsulfinyl, C ₁ -C ₈ alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, N(R ³ ) ₂ , CO ₂ R ² , O(CO)R ¹ , CON(R ³ ) ₂ , NR ³ COR ¹ , CR ¹ N-OR ² , wherein the alkyl group, cycloalkyl group, alkenyl group, alkynyl group, phenyl group and heterocyclic ring Optionally substituted with one or more groups, for example one to five groups, independently selected from halogen, CN, NH ₂ , NO ₂ , OR ² , C ₁ -C ₄ alkyl, C ₁ -C ₄ Haloalkyl.

Preferably, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other represent hydrogen, halogen, CN, NO ₂ , C ₁ -C ₈ alkyl, C ₃ -C ₈ naphthenic a C ₂ -C ₈ alkenyl group, 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 (the conditions are The heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms, such as a heterocycle as defined herein, preferably Lolinyl, pyrrolidinyl, piperidinyl, piperidine More preferably, pyridyl, pyrrolyl, imidazolyl or triazolyl (eg 1,2,4 triazolyl), more preferably Polinyl, pyrrolidinyl, pyridyl or imidazolyl), COR ¹ , OR ² , SH, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfinyl, C ₁ -C ₈ alkyl Sulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, N(R ³ ) ₂ , CO ₂ R ² , O(CO)R ¹ , CON(R ³ ) ₂ , NR ³ COR ¹ , CR ¹ N-OR ² , wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and heterocyclic ring are optionally substituted by one or more groups, for example one to five groups, independently It is selected from the group consisting of halogen, CN, NH ₂ , NO ₂ , OR ² , C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl.

More preferably, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other represent hydrogen, halogen, CN, OR ² , C ₁ -C ₈ alkyl, C ₂ -C ₈ alkenyl , C ₃ -C ₈ cycloalkyl, phenyl, pyridyl, CO ₂ R ² , N(R ³ ) ₂ , NR ³ COR ¹ , CR ¹ N-OR ² , SH, C ₁ -C ₈ -alkane sulfur group, C ₁ -C ₈ - alkylsulfinyl acyl, C ₁ -C ₈ - alkylsulfonyl, phenylthio, phenylsulfinyl or phenylsulfonyl sulfo acyl acyl, wherein the alkyl, alkenyl, The base, cycloalkyl, phenyl, and pyridyl groups are optionally substituted with one or more groups, for example one to five groups, independently selected from halo, CN, OR ² , C ₁ -C ₄ alkyl, and C ₁ -C ₄ haloalkyl.

Even more preferably, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other represent hydrogen, halogen, OR ² , CN, C ₁ -C ₄ alkyl, C ₃ -C ₆ ring An alkyl group, N(R ³ ) ₂ , phenyl, CO ₂ R ² or NR ³ COR ¹ , wherein the alkyl group, cycloalkyl group and phenyl group may be optionally substituted by one or more groups, for example one to five a group independently selected from the group consisting of halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ alkoxy, and C ₁ -C ₄ haloalkoxy.

More preferably, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other represent hydrogen, halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy a C ₃ -C ₆ alkenyloxy group, a C ₃ -C ₆ cycloalkyl group, N(R ³ ) ₂ , a phenyl group or a CO ₂ R ² wherein the alkyl group, the alkoxy group, the alkenyloxy group, the cycloalkane and phenyl optionally substituted with one or more groups, for example 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.

Even more preferably, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other represent hydrogen, C ₁ -C ₄ alkyl, CN or C ₁ -C ₄ alkoxy, wherein The alkyl group and the alkoxy group may be optionally substituted by one or more groups, for example one to five groups, independently selected from the group consisting of halogen, CN, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy base.

In one group of compounds, D ¹ , D ² , D ³ and D ⁴ independently of one another represent hydrogen, C ₁ -C ₄ alkyl, CN or C ₁ -C ₄ alkoxy, wherein the alkyl and alkoxy Optionally substituted with one or more groups, for example one to five groups, independently selected from halo, CN, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy; D ⁵ and D ⁶ independently of each other represents 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, 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 contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen An atom, for example a heterocyclic ring as defined herein, preferably a furyl, thiophenyl or pyrazolyl), COR ¹ , OR ² , SH, a C ₁ -C ₈ alkylthio group, a C ₁ -C ₈ alkane Isosulfonyl, C ₁ -C ₈ alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, N(R ³ ) ₂ , CO ₂ R ² , O(CO) R ¹ , CON(R ³ ) ₂ , NR ³ COR ¹ , CR ¹ N-OR ² , wherein the alkyl group, the cycloalkyl group, the alkenyl group, the alkynyl group, the phenyl group and the heterocyclic ring are allowed Optionally substituted with one or more groups, for example one to five groups, independently selected from the group consisting of halogen, CN, NH ₂ , NO ₂ , OR ² , C ₁ -C ₄ alkyl and C ₁ -C ₄ haloalkyl .

Preferably, in the group of compounds, D ¹ , D ² , D ³ and D ⁴ independently of each other represent hydrogen, C ₁ -C ₄ alkyl, CN or C ₁ -C ₄ alkoxy; D ⁵ and D ⁶ independently of each other represents hydrogen, CN, C ₁ -C ₄ alkyl, C ₃ -C ₈ cycloalkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl, phenyl, including one to three a 5-membered heterocyclic ring independently selected from the heteroatoms of O, S and N (provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms, for example as defined herein a heterocyclic ring, preferably a furyl, thiophenyl or pyrazolyl group, wherein the alkyl, alkenyl, alkynyl, phenyl and heterocyclic ring may be optionally substituted by one or more groups, for example One to five groups are independently selected from the group consisting of halogen, CN, NH ₂ , NO ₂ , C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, and C ₁ -C ₄ haloalkyl.

More preferably, in this group of compounds, D ¹ , D ² , D ³ and D ⁴ independently of each other represent hydrogen, C ₁ -C ₄ alkyl, CN or C ₁ -C ₄ alkoxy; D ⁵ and D ⁶ independently of each other represents hydrogen, C ₁ -C ₄ alkyl, phenyl, 5-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S and N (provided that the heterocyclic ring is not Included contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms, such as a heterocyclic ring as defined herein, preferably a furyl, thiophenyl or pyrazolyl group, wherein the phenyl and heterocyclic ring Optionally substituted with one or more groups, for example one to five groups, independently selected from halo, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl, and C ₁ -C ₄ haloalkyl .

Even more preferably, in this group of compounds, D ¹ , D ² , D ³ and D ⁴ independently of each other represent hydrogen; D ⁵ and D ⁶ independently of each other represent hydrogen, C ₁ -C ₄ alkyl, phenyl a 5-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S and N (provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms, For example, a heterocyclic ring as defined herein, preferably a furyl group, a thiophenyl group or a pyrazolyl group, wherein the phenyl group and the heterocyclic ring are optionally substituted by one or more groups, for example one to five groups The group is independently selected from the group consisting of halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl, and C ₁ -C ₄ haloalkyl.

In another group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other represent hydrogen, halogen, CN, NO ₂ , C ₁ -C ₈ alkyl, C ₃ -C ₈ a cycloalkyl group, a C ₂ -C ₈ alkenyl group, 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 (which The condition is that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms, such as a heterocyclic ring as defined herein, preferably a furyl, thiophenyl or pyrazolyl group, COR ¹ , OR ² , SH, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfinylene, C ₁ -C ₈ alkylsulfonyl, phenylthio, phenylsulfinyl , phenylsulfonyl, N(R ³ ) ₂ , CO ₂ R ² , O(CO)R ¹ , CON(R ³ ) ₂ , NR ³ COR ¹ , CR ¹ N-OR ² , wherein the alkyl group, The cycloalkyl, alkenyl, alkynyl, phenyl and heterocyclic ring may be optionally substituted by one or more groups, for example one to five groups, independently selected from halogen, CN, NH ₂ , NO ₂ , OR ² , C ₁ -C ₄ alkyl and C ₁ -C ₄ haloalkyl.

In this group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other preferably represent hydrogen, CN, C ₁ -C ₄ alkyl, C ₃ -C ₈ naphthenic. a C ₂ -C ₈ alkenyl group, a C ₂ -C ₈ alkynyl group, a phenyl group, a 5-membered heterocyclic ring containing one to three hetero atoms independently selected from O, S and N (the condition is: the hetero The ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms, such as a heterocyclic ring as defined herein, preferably a furyl, thiophenyl or pyrazolyl group, wherein the alkyl group, Alkenyl, alkynyl, phenyl and heterocyclic rings may be optionally substituted by one or more groups, for example one to five groups, independently selected from halogen, CN, NH ₂ , NO ₂ , C ₁ -C ₄ Alkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkyl.

In this group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ are each independently independently represented by hydrogen, C ₁ -C ₄ alkyl, phenyl, including one to three independently. a 5-membered heterocyclic ring selected from heteroatoms of O, S and N (provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms, for example as defined herein) a ring, preferably a furyl, thiophenyl or pyrazolyl group, wherein the phenyl group and the heterocyclic ring are optionally substituted by one or more groups, for example one to five groups, independently selected from halogen C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl, and C ₁ -C ₄ haloalkyl.

In this group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ are, independently of each other, even more preferably represent hydrogen, C ₁ -C ₄ alkyl, phenyl, containing one to three independent a 5-membered heterocyclic ring selected from the heteroatoms of O, S and N (provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms, for example as defined herein a heterocyclic ring, preferably a furyl, thiophenyl or pyrazolyl group, wherein the phenyl group and the heterocyclic ring are optionally independently selected from halo, C ₁ -C ₄ alkoxy, by one or more, Substitution of a C ₁ -C ₄ alkyl group and a C ₁ -C ₄ haloalkyl group.

In a subset of the group of compounds, D ¹ , D ² , D ³ and D ⁴ independently of one another represent hydrogen, C ₁ -C ₄ alkyl, CN or C ₁ -C ₄ alkoxy, wherein the alkyl group And the alkoxy group may be optionally substituted by one or more groups, for example one to five groups, independently selected from the group consisting of halogen, CN, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy, Wherein D ⁵ and D ⁶ are as defined above.

In a subgroup of the group of compounds, D ¹ , D ² , D ³ and D ⁴ are each independently independently represented by hydrogen, C ₁ -C ₄ alkyl, CN or C ₁ -C ₄ alkoxy, Wherein D ⁵ and D ⁶ are as defined above.

In a subset of this group of compounds, D ¹ , D ² , D ³ and D ⁴ are each preferably represented by hydrogen, wherein D ⁵ and D ⁶ are as defined above.

In another group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other represent hydrogen, halogen, C ₁ -C ₈ alkyl, C ₂ -C ₈ alkynyl, C ₁ -C ₈ alkoxy or C ₁ -C ₈ alkylthio.

More preferably, in this group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other represent hydrogen, halogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkyne a group, a C ₁ -C ₄ alkoxy group or a C ₁ -C ₄ alkylthio group.

Even more preferably, in this group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other represent hydrogen, halogen, methyl, ethynyl, methoxy or methylthio. .

Even more preferably, in this group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other represent hydrogen, chlorine, methyl, ethynyl, methoxy or methylthio. .

Most preferably, in this group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other represent hydrogen, methoxy or methylthio.

D ¹ and D ⁵ , D ² and D ⁵ , D ³ and D ⁶ , or D ⁴ and D ⁶ may form a carbocyclic or heterocyclic ring. This possibility and its preferred values are described below, which can be combined with any of the above definitions. Optionally, the above definitions may exclude the possibility of a ring formed by D ¹ and D ⁵ , D ² and D ⁵ , D ³ and D ⁶ , or D ⁴ and D ⁶ .

D ¹ and D ⁵ , D ² and D ⁵ , D ³ and D ⁶ , D ⁴ and D ⁶ together with the ring segments 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 containing one to three heteroatoms independently selected from O, S, N and N(R ³ ) (provided that the heterocyclic ring does not contain contiguous An oxygen atom, an adjacent sulfur atom or an adjacent sulfur and oxygen atom), and wherein a ring formed by D ¹ and D ⁵ , D ² and D ⁵ , D ³ and D ⁶ , D ⁴ and D ⁶ may optionally be Substituted by one or more groups, for example one to five groups, independently selected 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 ₄ haloalkoxy. Examples of possible ring segments formed by D ¹ and D ⁵ , D ² and D ⁵ , D ³ and D ⁶ , or D ⁴ and D ⁶ include -CH=CH-CH=CH-, -CH ₂ -CH ₂ -CH ₂ -CH ₂ -, -CH ₂ -CH ₂ -CH ₂ -, -N=CH-N=CH-, -CH=N-CH=N-, -N=N-CH=N-, -N=CH-N=N-, -CH=CH-S-, -S-CH=CH-, -CH=CH-NH-, -NH-CH=CH-, in each case, any hydrogen Atoms can be replaced as indicated.

Preferably, D ¹ and D ⁵ , D ² and D ⁵ , D ³ and D ⁶ , D ⁴ and D ⁶ together with the ring segments to which they are attached may form partially or fully unsaturated 5- to 7 a meta carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R ³ ), and wherein from D ¹ and D ⁵ , D ² and D ⁵ , D ³ The ring formed with D ⁶ , D ⁴ and D ⁶ may be optionally substituted by one or more groups, for example one to five groups, independently selected 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 ₄ haloalkoxy.

More preferably, D ¹ and D ⁵ , D ² and D ⁵ , D ³ and D ⁶ , D ⁴ and D ⁶ together with the ring segments to which they are attached may form partially or fully unsaturated 5- to 7 a carbocyclic ring wherein the ring formed by D ¹ and D ⁵ , D ² and D ⁵ , D ³ and D ⁶ , D ⁴ and D ⁶ may be optionally substituted by one or more groups, for example one to five The group is independently selected from the group consisting of halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, and C ₁ -C ₄ haloalkoxy.

In a preferred group of compounds, D ¹ and D ⁵ , D ² and D ⁵ , D ³ and D ⁶ , D ⁴ and D ⁶ together with the ring segments to which they are attached are not partially or fully unsaturated. A 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R ³ ).

X represents X-2, X-3, X-4 or X-5. Preferably, X represents X-3, X-4 or X-5. More preferably, X represents X-3 or X-5. Even more preferably, X represents X-3.

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 independently of each other represent CR ⁴ R ⁵ , C=O or C= CR ⁶ R ^{7 is} preferably CR ⁴ R ⁵ or C=CR ⁶ R ⁷ , more preferably CR ⁴ R ⁵ .

Z ⁴ and Z ¹² represent CR ⁸ R ⁹ , SiR ¹⁰ R ¹¹ , C=O or C=CR ⁶ R ⁷ , preferably CR ⁸ R ⁹ or C=CR ⁶ R ⁷ .

When X is X-2, it is preferred that one of Z ¹ and Z ^{2 is} a methylene group or a halogenated methylene group, 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, more preferably, Z ³ , Z ⁴ and Z. ⁵ wherein both are independently methylene or halomethylene, preferably methylene. Preferably, Z ³ and Z ⁵ are methylene or halomethylene, preferably methylene.

When X is X-4, it is preferred that at least three of Z ⁶ , Z ⁷ , Z ⁸ and Z ⁹ are substituted only by hydrogen or halogen, preferably hydrogen, more preferably, Z ⁶ , Z. At least three of ⁷ , Z ⁸ and Z ⁹ are independently methylene or halomethylene, preferably methylene.

When X is X-5, it is preferred that at least four of Z ¹⁰ , Z ¹¹ , Z ¹² , Z ¹³ and Z ¹⁴ are substituted only by hydrogen or halogen, preferably hydrogen, and more preferably, Z. ¹⁰ , four of Z ¹¹ , Z ¹² , Z ¹³ and Z ¹⁴ are independently methylene or halomethylene, preferably methylene. Preferably, Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ^{14 are} independently methylene or halomethylene, preferably methylene.

The groups X-2, X-3, X-4 and X-5 comprise at most one ring comprising only one of the Z ¹ to Z ¹⁴ groups or two of the Z ¹ to Z ¹⁴ groups or Z ¹ to Z ¹⁴ or the three groups Z ¹ to Z ¹⁴ in the four groups as ring members. 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 two OH groups. Substituted carbon atoms. Optionally, the groups Z ¹ , Z ³ , Z ⁶ and Z ^{10 are} not substituted by OH.

In a preferred group of compounds, the groups X-2, X-3, X-4 and X-5 do not comprise any ring containing a Z ¹ to Z ¹⁴ group.

The Q system is selected from the group consisting of Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, and Q-9. . Q-1, Q2, Q-3 and Q-9 are preferred. The Q' is selected from the group consisting of Q-1', Q-2', Q-3', Q-4', Q-5', Q-6', Q-7'. , Q-8' and Q-9'. Q-1', Q2', Q-3' and Q-9' are preferred.

In a group of compounds, the Q system is selected from the group consisting of Q-1, Q-2, Q-4, Q-5, Q-6, Q-7, Q-8, and Q. -9. Q-1, Q2 and Q-9 are preferred. The Q' is selected from the group consisting of Q-1', Q-2', Q-4', Q-5', Q-6', Q-7', Q-8'. And Q-9'. Q-1', Q2' and Q-9' are preferred.

Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently 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, benzyl, 5- or 1 to 3 heteroatoms independently selected from O, S and N a 6-membered heterocyclic ring (provided that the heterocyclic ring does not contain an adjacent oxygen atom, an adjacent sulfur atom or an adjacent sulfur and oxygen atom, such as a heterocyclic ring as defined herein, preferably Lolinyl, pyrrolidinyl, piperidinyl, piperidine More preferably, pyridyl, pyrrolyl, imidazolyl or triazolyl (eg 1,2,4 triazolyl), more preferably Polinyl, pyrrolidinyl, pyridyl or imidazolyl), COR ¹ , OR ² , SH, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfinyl, C ₁ -C ₈ alkyl Sulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, N(R ³ ) ₂ , CO ₂ R ² , O(CO)R ¹ , CON(R ³ ) ₂ , NR ³ COR ¹ , CR ¹ N-OR ² , wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and heterocyclic ring may be optionally substituted by one or more groups, for example one to five groups The group is independently selected from the group consisting of halogen, CN, NH ₂ , NO ₂ , OR ² , C ₁ -C ₄ alkyl, and C ₁ -C ₄ haloalkyl.

Preferably, Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently represent hydrogen, halogen, CN, OR ² , C ₁ -C _8- alkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl, C ₃ -C ₈ cycloalkyl, phenyl, pyridyl, N(R ³ ) ₂ , CO ₂ R ² , NR ³ COR ¹ , SH, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfinyl, C ₁ -C ₈ alkylsulfonyl, phenylthio, phenylsulfinyl or phenylsulfonate A mercapto group, wherein the alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, and pyridyl groups are optionally substituted with one or more groups, for example one to five groups, independently selected from halo, CN And OR ² , C ₁ -C ₄ alkyl and C ₁ -C ₄ haloalkyl.

More preferably, Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently represent hydrogen, halogen, OR ² , CN, C ₁ -C _4- alkyl, C ₃ -C ₆ cycloalkyl, N(R ³ ) ₂ , C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonate a phenyl group, a phenyl group, a CO ₂ R ² or NR ³ COR ¹ , wherein the alkyl group, the cycloalkyl group and the phenyl group are optionally substituted by one or more groups, for example 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.

More preferably, Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently 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 ³ ) ₂ , C ₁ -C ₄ alkylthio, C ₁ - C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, phenyl, phenyloxyl or CO ₂ R ² wherein the alkyl, alkoxy, alkenyloxy, naphthenic and phenyl optionally substituted with one or more groups, for example 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.

More preferably, Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently represent hydrogen, C ₁ -C ₄ alkyl, CN or a C ₁ -C ₄ alkoxy group, wherein the alkyl group and the alkoxy group are optionally substituted by one or more groups, for example one to five groups, independently selected from halogen, CN, C ₁ -C ₄ Alkoxy and C ₁ -C ₄ haloalkoxy.

In a group of compounds, Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently represent hydrogen, halogen, OH, CN, C ₁ -C _{a 4-} alkyl group, a C ₁ -C ₄ alkoxy group, a phenyl group, wherein the alkyl group, the alkoxy group and the phenyl group are optionally substituted by one or more groups, for example 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.

In this group of compounds, Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} are each independently independently represented by hydrogen, halogen, OH, C _{1 .} a C ₄ alkyl group, a C ₁ -C ₄ alkoxy group, a phenyl group, wherein the phenyl group may be optionally substituted with one or more groups, for example 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.

In this group of compounds, Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} are each independently independently more preferably represent hydrogen, halogen, OH, C _{1 .} -C ₄ alkyl, phenyl, wherein the phenyl group may be optionally substituted by one or more groups, for example one to five groups, independently selected from halogen, CN, C ₁ -C ₄ alkyl.

In this group of compounds, Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} are each independently, even more preferably, represent hydrogen, halogen, OH, C. ₁ -C ₄ alkyl, phenyl, wherein the phenyl group is optionally substituted by one or more groups, for example one to five groups, independently selected from C ₁ -C ₄ alkyl.

In this group of compounds, Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} are each independently independently more preferably represent hydrogen, OH, C ₁ - C ₄ alkyl, phenyl, wherein the phenyl group may be optionally substituted by one or more groups, for example one to five groups, independently selected from C ₁ -C ₄ alkyl.

In another group of compounds, Y ¹ , Y ² , Y ³ , Y ^{1 '} , Y ^{2 '} and Y ^{3 '} each independently represent hydrogen or C ₁ -C ₄ alkyl; Y ⁴ and Y ^{4 '} are each other Independently representing hydrogen, halogen, OH, C ₁ -C ₄ alkyl, phenyl, wherein the phenyl group may be optionally substituted with one or more groups, for example one to five groups, independently selected from C ₁ -C ₄ alkyl.

In this group of compounds, Y ¹ , Y ² , Y ³ , Y ^{1 '} , Y ^{2 '} and Y ^{3 '} are each independently independently represented by hydrogen or C ₁ -C ₄ alkyl; Y ⁴ and Y ^{4 'are} each independently of each other preferably represents a hydrogen, OH, C ₁ -C ₄ alkyl, phenyl, wherein the phenyl group may be optionally substituted by one or more groups, for example one to five groups independently It is selected from a C ₁ -C ₄ alkyl group.

In another group of compounds, Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently represent hydrogen, halogen, C ₁ -C ₈ alkyl a C ₂ -C ₈ alkynyl group, a C ₁ -C ₈ alkoxy group or a C ₁ -C ₈ alkylthio group.

More preferably, in this group of compounds, Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently represent hydrogen, halogen, C ₁ - C ₄ alkyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio.

Even more preferably, in this group of compounds, Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently represent hydrogen, halogen, methyl , ethynyl, methoxy or methylthio.

More preferably, in this group of compounds, Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently represent hydrogen, chlorine, methyl , ethynyl, methoxy or methylthio.

Most preferably, in this group of compounds, Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently represent hydrogen, methoxy or A Sulfur based.

When Q system Q-1, Q-2, Q-3, Q-4, Q-6 or Q-7, then Y ¹ and Y ² , Y ² and Y ³ , or Y ³ and Y ⁴ are independent of each other A carbocyclic or heterocyclic ring may be formed along with the fragments to which they are attached. Similarly, Q' is Q-1', Q-2', Q-3', Q-4', Q-6' or Q-7', then Y ^{1 '} and Y ^2' , Y ^2' and Y ^3' or Y ^{3 '} and Y ^4' may form a carbocyclic or heterocyclic ring. This possibility and its preferred values are described below, which can be combined with any of the above definitions.

When Q system Q-1, Q-2, Q-3, Q-4, Q-6 or Q-7, then Y ¹ and Y ² , Y ² and Y ³ , or Y ³ and Y ⁴ are independent of each other Together with the fragments to which they are attached, a partially or fully unsaturated 5- to 7-membered carbocyclic ring or partially or fully unsaturated, including one to three independently selected from O, S, N and N, may be formed ( a 5- to 7-membered heterocyclic ring of a hetero atom of R ³ ) (provided that the heterocyclic ring does not contain an adjacent oxygen atom, an adjacent sulfur atom or an adjacent sulfur and oxygen atom, such as Y ¹ and Y ² , Y ² and Y ³ , or Y ³ and Y ⁴ together with the ring segment to which they are attached may form a ring system selected from the group consisting of: isoquinoline; 5,6,7,8-tetrahydro-isoquinoline; 6,7-dihydro-5H-[2]pyridine; 3,4-dihydro-1H-piperacino[3,4-c]pyridine; 6,7,8,9-tetrahydro-5H-cycloheptane Alkane [c]pyridine; [1,7] Acridine; quinoline; 5,6,7,8-tetrahydro-quinoline; 6,7-dihydro-5H-[1]pyridine; [1,8] a pyridine; 6,7,8,9-tetrahydro-5H-cycloheptane [b]pyridine; and 7,8-dihydro-5H-piperido[4,3-b]pyridine), and wherein The ring formed by ¹ and Y ² , Y ² and Y ³ , or Y ³ and Y ⁴ may be optionally substituted by one or more groups, for example one to five groups, independently selected from halogen, CN, NH ₂ And 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. When Q' is Q-1', Q-2', Q-3', Q-4', Q-6' or Q-7', the above also applies to Y ^{1 '} and Y ^2' , Y ^{2 '} and Y ^3' , or Y ^3' and Y ^4' .

Preferably, Y ¹ and Y ² , Y ² and Y ³ , or each combination of Y ³ and Y ⁴ independently of each other together with the ring segments to which they are attached may form a partially or fully unsaturated 5- to a 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R ³ ), and wherein Y ¹ and Y ² , Y ² and Y ³ , or The ring formed by Y ³ and Y ⁴ may be optionally substituted by one or more groups, for example one to five groups, independently selected from halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkane. 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. The above also applies to Y ^{1 '} and Y ^{2 '} , Y ^{2 '} and Y ^{3 '} , or Y ^{3 '} and Y ^{4 '} .

More preferably, Y ¹ and Y ² , Y ² and Y ³ , or each combination of Y ³ and Y ⁴ independently of each other together with the ring segments to which they are attached may form a partially or fully unsaturated 5- to a 7-membered carbocyclic ring wherein the ring formed by Y ¹ and Y ² , Y ² and Y ³ , or Y ³ and Y ⁴ may be optionally substituted by one or more groups, for example one to five groups, independently It is 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 and C ₁ -C ₄ alkylthio. The above also applies to Y ^{1 '} and Y ^{2 '} , Y ^{2 '} and Y ^{3 '} , or Y ^{3 '} and Y ^{4 '} .

More preferably, each of Y ² and Y ³ together with the ring segments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by Y ² and Y ³ may optionally be Substituted by one or more groups, for example one to five 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 and C ₁ -C ₄ alkylthio. The above also applies to Y ^{2 '} and Y ^3' .

More preferably, Y ² and Y ³ together with the fragments to which they are attached may form a fully unsaturated 6-membered carbocyclic ring and wherein the ring formed by Y ² and Y ³ may optionally be passed through one or more a group substituted, for example one to five 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 haloalkane Oxyl and C ₁ -C ₄ alkylthio. The above also applies to Y ^{2 '} and Y ^3' .

In a group of compounds, Y ² and Y ³ together with the ring segments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y ² and Y ³ may optionally be passed through a ring. Or a plurality of groups substituted, for example one to five groups, independently selected from C ₁ -C ₄ alkyl. The above also applies to Y ^{2 '} and Y ^3' .

In another group of compounds, when Q is Q-2, Y ² and Y ³ together with the ring segments to which they are attached may form only a ring. The above also applies to Y ^{2 '} and Y ^3' .

In another group of compounds, Y ² and Y ³ together with the fragments to which they are attached may form a fully unsaturated 6-membered carbocyclic ring and wherein the ring formed by Y ² and Y ³ may optionally be subjected to one or Substituted by a plurality of groups, for example one to five 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 and C ₁ -C ₄ alkylthio. When Q is Q-1, Q-3, Q-4, Q-7 or Q-8 and L ¹ is CD ¹ , then Y ¹ and D ¹ together with the fragments to which they are attached may form a carbocyclic or Heterocyclic. Similarly, when Q' is Q-1', Q-3', Q-4', Q-7' or Q-8', then Y ^{1 '} and D ⁴ together with the fragments to which they are attached may A carbocyclic or heterocyclic ring is formed. This possibility and its preferred values are described below, which can be combined with any of the above definitions.

When Q is Q-1, Q-3, Q-4, Q-7 or Q-8 and L ¹ is CD ¹ , then Y ¹ and D ¹ together with the fragments to which they are attached may form part or all An unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one or two heteroatoms independently selected from O, S, N and N(R ³ ) a ring (provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms), and wherein the ring formed by D ¹ and Y ¹ may optionally be through one or more groups Group substituted, for example one to five groups, independently selected 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. The above also applies to Y ^{1 '} and D ⁴ when Q' is Q-1', Q-3', Q-4', Q-7' or Q-8'. Examples of ring fragments which may be formed by Y ¹ and D ¹ , Y ^{1 '} and D ⁴ include CH=CH-, -CH ₂ -CH ₂ -, -CH ₂ -CH ₂ -CH ₂ -, CH ₂ -NH- CH ₂ -, -CH ₂ -O-CH ₂ -, in each case, any hydrogen atom may be substituted as indicated.

Preferably, when Q is Q-1, Q-3, Q-4, Q-7 or Q-8 and L ¹ is CD ¹ , then Y ¹ and D ¹ together with the fragments to which they are attached A partially or fully unsaturated 5- to 7-membered carbocyclic ring or a partially or fully unsaturated 5- to 7-membered one or two heteroatoms independently selected from N and N(R ³ ) may be formed. a heterocyclic ring wherein the ring formed by D ¹ and Y ¹ may be optionally substituted by one or more groups, for example one to five groups, independently selected from halogen, CN, OH, C ₁ -C ₄ alkyl And 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. The above also applies to Y ^{1 '} and D ⁴ when Q' is Q-1', Q-3', Q-4', Q-7' or Q-8'.

Preferably, when Q is Q-1, Q-3, Q-4, Q-7 or Q-8 and L ¹ is CD ¹ , then Y ¹ and D ¹ together with the fragments to which they are attached A partially or fully unsaturated 5- to 7-membered carbocyclic ring may be formed wherein the ring formed by D ¹ and Y ¹ may be optionally substituted with one or more groups, for example one to five groups, independently selected From halogen, CN, 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. The above also applies to Y ^{1 '} and D ⁴ when Q' is Q-1', Q-3', Q-4', Q-7' or Q-8'.

More preferably, when Q is Q-1, Q-3, Q-4, Q-7 or Q-8 and L ¹ is CD ¹ , then Y ¹ and D ¹ together with the fragments to which they are attached A partially or fully unsaturated 6-membered carbocyclic ring may be formed wherein the ring formed by D ¹ and Y ¹ may be optionally substituted with one or more groups, for example one to four groups, independently selected from halogen, CN, 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. The above also applies to Y ^{1 '} and D ⁴ when Q' is Q-1', Q-3', Q-4', Q-7' or Q-8'.

Even more preferably, when Q is Q-1, Q-3, Q-4, Q-7 or Q-8 and L ¹ is CD ¹ , then Y ¹ and D ¹ together with the one to which they are attached The fragment may form a fully unsaturated 6-membered carbocyclic ring wherein the ring formed by D ¹ and Y ¹ may be optionally substituted with one or more groups, for example one or two independently selected from the group consisting of halogen, CN, OH a group of a C ₁ -C ₄ alkyl group, 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. The above also applies to Y ^{1 '} and D ⁴ when Q' is Q-1', Q-3', Q-4', Q-7' or Q-8'.

Most preferably, when Q is Q-1, Q-3, Q-4, Q-7 or Q-8 and L ¹ is CD ¹ , then Y ¹ and D ¹ together with the fragments to which they are attached A fully unsaturated 6-membered carbocyclic ring may be formed wherein the ring formed by D ¹ and Y ¹ may be optionally substituted with one or more groups, for example one or two groups, independently selected from halo, CN , OH, methyl, halomethyl, methoxy and halomethoxy. The above also applies to Y ^{1 '} and D ⁴ when Q' is Q-1', Q-3', Q-4', Q-7' or Q-8'.

In a group of compounds, wherein Q is Q-1 or Q-3 and L ¹ is CD ¹ , then Y ¹ and D ¹ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbon. a ring wherein the ring formed by D ¹ and Y ¹ may be optionally substituted with one or more groups, for example one to four groups, independently selected from halogen, CN, 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. The above also applies to Y ^{1 '} and D ⁴ in the group of compounds in which Q' is Q-1' or Q-3'.

More preferably, in this group of compounds, Y ¹ and D ¹ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D ¹ and Y ¹ may be Optionally substituted with one or more groups, for example one or two groups, independently selected from halo, CN, OH, methyl, halomethyl, methoxy and halomethoxy. The above also applies to Y ^{1 '} and D ⁴ in the group of compounds in which Q' is Q-1' or Q-3'.

Most preferably, in this group of compounds, Y ¹ and D ¹ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring. The above also applies to Y ^{1 '} and D ⁴ in the compound group of Q-1' or Q' system Q-3'.

Preferably, in this group of compounds, the Q line Q-1 and/or the Q' line Q-1'. When Q is Q-9 and L ¹ is CD ¹ , then R ¹² and D ¹ may together be -(G ¹ ) _p -G ² -G ³ -. Similarly, when Q 'line Q-9' and the line L ⁴ CD ^4, the R ¹² 'D ⁴ may be together with the _{^{- (G 1) p -G 2}} -G 3 -.

G ¹ and G ² independently of each other represent -C(R ¹⁴ R ¹⁵ )-; G ³ represents -C(R ¹⁴ R ¹⁵ )-, O, N(R ¹⁶ ) or S; or G ¹ and G ² , or G ² and G ³ , or G ¹ and G ¹ together represent -CR ¹⁴ =CR ¹⁵ -. Preferably, G ¹ , G ² and G ³ represent C(R ²¹ ) ₂ , wherein each R ²¹ independently of one another represents hydrogen, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy, preferably hydrogen or C ₁ -C ₄ alkyl. More preferably, G ¹ , G ² and G ³ represent a methylene group.

Each p represents 0, 1 or 2 independently of each other, preferably 1 or 2, more preferably 1.

Each R ¹ independently of ^one another 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 And wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl, and pyridyl groups are optionally substituted with one or more groups, for example one to five groups, independently selected from halo , 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. Preferably, each R ¹ independently of ^one another represents hydrogen, C ₁ -C ₈ alkyl or C ₁ -C ₈ haloalkyl.

In a group of compounds, each R ¹ independently of ^one another represents hydrogen, C ₁ -C ₄ alkyl or phenyl, wherein the alkyl and phenyl are optionally substituted by one or more groups, for example one to five a group independently 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, and C ₁ -C ₄ Haloalkoxy.

Preferably, in the group of compounds, each R ¹ independently of ^one another represents hydrogen, C ₁ -C ₄ alkyl or phenyl, wherein the alkyl and phenyl are optionally via one or more groups Substituents, for example one to five groups, are independently selected from halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy.

More preferably, in this group of compounds, each R ¹ independently of ^one another represents hydrogen, C ₁ -C ₄ alkyl or phenyl, wherein the phenyl group may be substituted with one or more groups, for example one to five The group is independently selected from the group consisting of halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, and C ₁ -C ₄ haloalkoxy.

Even more preferably, in this group of compounds, each R ¹ independently of ^one another represents hydrogen or phenyl, wherein the phenyl group may be substituted with one or more groups, for example one to five groups, independently selected from Halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, and C ₁ -C ₄ haloalkoxy.

Most preferably, in this group of compounds, each R ¹ independently of ^one another represents hydrogen or phenyl.

Each R ² independently of one another represents hydrogen, C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl, phenyl, benzyl or One to three 5- or 6-membered heterocyclic rings independently selected from the heteroatoms of O, S and N (provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms Wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and heterocyclic ring may be optionally substituted by one or more groups, for example one to five groups, independently selected from halo , 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 ₁ -C ₄ -alkyl-C ₁ -C ₄ -alkoxy and C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl. The heterocyclic ring is preferably one as defined herein, preferably Lolinyl, pyrrolidinyl, piperidinyl, piperidine More preferably, pyridyl, pyrrolyl, imidazolyl or triazolyl (eg 1,2,4 triazolyl), more preferably A phenyl group, a pyrrolidinyl group, a pyridyl group or an imidazolyl group.

Preferably, each R ² independently of one another represents hydrogen, C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl, phenyl 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 contiguous oxygen atoms, contiguous sulfur atoms or adjacent Sulfur and oxygen atoms), wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and heterocyclic ring may be optionally substituted by one or more groups, for example one to five groups, Independently selected 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 -alkoxy-C ₁ -C ₄ -alkyl.

Preferably, each R ² independently of one another represents hydrogen, C ₁ -C ₈ alkyl, C ₁ -C ₈ haloalkyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ alkenyl, C ₃ a -C ₈ haloalkenyl group, a C ₃ -C ₈ alkynyl group, a C ₃ -C ₈ haloalkynyl group, a phenyl group, a benzyl group or a pyridyl group, wherein the phenyl group, the benzyl group and the pyridyl group are optionally Substituted by one or more groups, for example one to five groups, independently selected from halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ alkoxy group and C ₁ -C ₄ haloalkoxy group.

More preferably, each R ² independently of one another represents hydrogen, C ₁ -C ₈ alkyl, C ₁ -C ₈ haloalkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ haloalkenyl, C _{a 3-} C ₈ haloalkynyl, phenyl, benzyl or pyridyl group, wherein the phenyl, benzyl and pyridyl groups are optionally substituted by one or more groups, for example one to five groups, independently It is 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, and C ₁ -C ₄ haloalkoxy.

More preferably, each R ² independently of one another represents hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₃ -C ₆ alkenyl or C ₃ -C ₆ haloalkenyl.

More preferably, each R ² independently of one another represents hydrogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl.

In one group of compounds, each R ² independently of one another represents hydrogen, C ₁ -C ₄ alkyl or C ₃ -C ₆ alkenyl.

Each R ³ independently of one another 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 a -C ₈ alkenyl group, a C ₃ -C ₈ alkynyl group or COR ¹ , wherein the alkyl group, alkoxy group, alkenyl group and alkynyl group are optionally substituted by one or more, for example one to five, halogens; When two groups R ^{3 are} attached to the same nitrogen atom, the groups may be the same or different; wherein when two groups R ^{3 are} attached to the same nitrogen atom, both groups are It may not be OH, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy; and wherein when two groups R ^{3 are} attached to the same nitrogen atom, the two groups are attached together with them The nitrogen atom thereto may form a ring B-1, B-2, B-3, B-4, B-5, B-6, B-7 or B-8, wherein the ring formed may optionally be Substituted by one or more groups, for example one to five groups, independently selected 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 ₄ haloalkoxy.

Preferably, each R ³ independently of one another represents hydrogen, C ₁ -C ₈ alkyl or COR ¹ ; wherein when two groups R ^{3 are} attached to the same nitrogen atom, the groups may be the same Or different; and wherein when two groups R ^{3 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 optionally substituted with one or more groups, for example one to five groups, independently selected from halo, methyl or halomethyl.

More preferably, each R ³ independently of one another represents hydrogen or C ₁ -C ₄ alkyl; wherein when two groups R ^{3 are} attached to the same nitrogen atom, the groups may be the same or different And wherein when two groups R ^{3 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 optionally substituted with one or more groups, for example one to five groups, independently selected from halo, methyl or halomethyl.

More preferably, each R ³ independently of one another represents hydrogen or C ₁ -C ₄ alkyl.

Most preferably, each R ³ represents hydrogen.

R ⁴ and R ⁵ each independently represent hydrogen, halogen, CN, OH, SH, CHO, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ alkynyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkoxycarbonyl, C ₃ -C ₆ cycloalkyl , CON(R ³ ) ₂ , NH ₂ , NR ³ COR ¹ , CR ¹ N-OR ² , phenyl or 5- or 6-membered hetero-containing one to four heteroatoms independently selected from O, S and N a ring (provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms), wherein the alkyl, alkenyl, alkynyl, phenyl and heterocyclic rings may optionally be One or more independently selected from the group consisting of halogen, OH, OR ² , CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy Substituted with a C ₁ -C ₄ alkylthio group, a C ₁ -C ₄ haloalkylthio group, a CON(R ³ ) ₂ , NH ₂ , NR ³ COR ¹ and a phenyl group; or R ⁴ and R ⁵ together with The carbon atom attached thereto may form a C ₃ -C ₆ cycloalkyl group or a C ₃ -C ₆ halocycloalkyl group.

Preferably, R ⁴ and R ⁵ each independently represent hydrogen, halogen, CN, OH, SH, CHO, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl , C ₁ -C ₆ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ alkynyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkoxycarbonyl, C ₃ - C ₆ cycloalkyl, CON(R ³ ) ₂ , NH ₂ , NR ³ COR ¹ , CR ¹ N-OR ² , phenyl or 5--containing one to four heteroatoms independently selected from O, S and N Or a 6-membered heterocyclic ring (provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms), wherein the alkyl, alkenyl, alkynyl, phenyl and heterocyclic rings Optionally, one or more independently selected from the group consisting of halogen, OH, OR ² , CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ - Substituents of C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, CON(R ³ ) ₂ , NH ₂ , NR ³ COR ¹ and phenyl groups.

More preferably, R ⁴ and R ⁵ each independently represent hydrogen, halogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C _1- C ₄ alkoxy, C ₃ -C ₄ alkenyloxy, C ₁ -C ₄ alkoxycarbonyl, C ₃ -C ₆ cycloalkyl, CON(R ³ ) ₂ , NH ₂ , NR ³ COR ¹ Or CR ¹ N-OR ² , wherein the alkyl, alkenyl, alkynyl group is optionally independently selected from halo, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ via one or more Substituted by a haloalkyl group, a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ haloalkoxy group, and a NH ₂ group.

More preferably, R ⁴ and R ⁵ each independently represent hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkoxycarbonyl, CON(R ³ ) ₂ And NH ₂ , NR ³ COR ¹ or CR ¹ N-OR ² , wherein the alkyl group is optionally substituted with one or more groups independently selected from the group consisting of halogen, OH, CN, and NH ₂ .

More preferably, R ⁴ and R ⁵ each independently represent hydrogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxycarbonyl, wherein the alkyl group may optionally be independently or in one or more Substituted by a group selected from halogen.

More preferably, R ⁴ and R ⁵ each independently represent hydrogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxycarbonyl.

More preferably, R ⁴ and R ⁵ each independently represent hydrogen, C ₁ -C ₄ alkyl or C ₁ -C ₂ alkoxycarbonyl.

More preferably, R ⁴ and R ⁵ each independently represent hydrogen or a C ₁ -C ₂ alkoxycarbonyl group.

Most preferably, R ⁴ and R ⁵ each represent hydrogen.

In one group of compounds, R ⁴ and R ⁵ each independently represent hydrogen, halogen, CN, OH, SH, CHO, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkenyl, C ₁ -C ₆ alkyne , C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkenyloxy, C ₁ -C ₆ alkynyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkoxycarbonyl, C ₃ a C ₆ cycloalkyl group, a phenyl group or a 5- or 6-membered heterocyclic ring containing one to three hetero atoms independently selected from O, S and N (provided that the heterocyclic ring does not contain contiguous oxygen atoms, a sulfur atom or abutting adjacent sulfur and oxygen atoms), wherein the alkyl, alkenyl, alkynyl, phenyl and heterocycle optionally substituted with one or more groups independently selected from halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, and C ₁ -C ₄ haloalkylthio The group is substituted; or R ⁴ and R ⁵ 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. Examples of the heterocyclic ring include dioxolane, dithiolan, Lolinyl, pyrrolidinyl, piperidinyl, piperidine A pyridyl group, a pyrrolyl group, an imidazolyl group or a triazolyl group (for example, 1,2,4triazolyl), more preferably a dioxolane, a dithiolane, a pyridyl group or an imidazolyl group.

Preferably, R ⁴ and R ⁵ each independently represent hydrogen, halogen, CN, OH, SH, CHO, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkenyl , C ₁ -C ₆ haloalkenyl, C ₁ -C ₆ alkynyl, C ₁ -C ₆ haloalkynyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ - C ₆ alkenyloxy, C ₁ -C ₆ haloalkenyloxy, C ₁ -C ₆ alkynyloxy, C ₁ -C ₆ haloalkynyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ haloalkoxycarbonyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl or phenyl, wherein The phenyl group may be optionally independently selected from halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkane by one or more The group of the oxy group is substituted; or R ⁴ and R ⁵ 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, R ⁴ and R ⁵ each independently represent hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ a C ₄ alkenyloxy group or a phenyl group, wherein the phenyl group may be optionally substituted by one or more groups, for example one to five groups, independently selected from the group consisting of halogen, CN, methyl, halomethyl, a methoxy group and a halogenated methoxy group; or R ⁴ and R ⁵ 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 group.

More preferably, R ⁴ and R ⁵ each independently represent hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkenoxy or C ₁ -C ₄ haloalkyl; or R ⁴ and R ⁵ 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 ⁴ and R ⁵ each independently represent hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl.

In one group of compounds, R ⁴ and R ⁵ each independently represent hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or phenyl, wherein the phenyl group is optional One or more groups independently selected from the group consisting of halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, and C ₁ -C ₄ haloalkoxy Substituting; or R ⁴ and R ⁵ 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.

R ⁶ and R ⁷ each independently represent hydrogen, halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl. Preferably, R ⁶ and R ⁷ each independently represent hydrogen, halogen, methyl or halomethyl.

Most preferably, R ⁶ and R ⁷ each represent hydrogen.

R ⁸ and R ⁹ each independently represent hydrogen, halogen, CN, OH, SH, CHO, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ alkynyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkoxycarbonyl, C ₃ -C ₆ cycloalkyl , CON(R ³ ) ₂ , NH ₂ , NR ³ COR ¹ , CR ¹ N-OR ² , phenyl or 5- or 6-membered hetero-containing one to four heteroatoms independently selected from O, S and N a ring (provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms), wherein the alkyl, alkenyl, alkynyl, phenyl and heterocyclic rings may optionally be One or more independently selected from the group consisting of halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, benzyloxy Substituted with a group of C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, CON(R ³ ) ₂ , NH ₂ , NR ³ COR ¹ and phenyl; or R ⁸ and R ⁹ together with them The carbon atom attached thereto may form a C ₃ -C ₆ cycloalkyl group or a C ₃ -C ₆ halocycloalkyl group.

Preferably, R ⁸ and R ⁹ each independently represent hydrogen, halogen, CN, OH, SH, CHO, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl , C ₁ -C ₆ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ alkynyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkoxycarbonyl, C ₃ - C ₆ cycloalkyl, CON(R ³ ) ₂ , NH ₂ , NR ³ COR ¹ , CR ¹ N-OR ² , phenyl or 5--containing one to four heteroatoms independently selected from O, S and N Or a 6-membered heterocyclic ring (provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms), wherein the alkyl, alkenyl, alkynyl, phenyl and heterocyclic rings Optionally, one or more independently selected from the group consisting of halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkane Substituents of oxy, benzyloxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, CON(R ³ ) ₂ , NH ₂ , NR ³ COR ¹ and phenyl groups.

More preferably, R ⁸ and R ⁹ each independently represent hydrogen, halogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C _1- C ₄ alkoxy C ₃ -C ₄ alkenyloxy, C ₃ -C ₄ alkynyloxy, C ₁ -C ₄ alkoxycarbonyl, C ₃ -C ₆ cycloalkyl, CONH ₂ , CONH(C ₁ -C ₄ alkyl), CON(C ₁ -C ₄ alkyl) ₂ , NH ₂ , NR ³ CO(C ₁ -C ₄ alkyl), NR ³ CO(C ₂ -C ₄ alkenyl), NR ³ CO(C ₂ -C ₄ alkynyl), NR ³ CO phenyl, CHN-OR ² , phenyl or a 5-membered heterocyclic ring containing one to four independent heteroatoms selected from O and N (the conditions are The heterocyclic ring does not comprise an contiguous oxygen atom), wherein the alkyl, alkenyl, alkynyl, phenyl and heterocyclic ring are optionally independently selected from one or more of halogen, OH, CN, C ₁ - C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, benzyloxy, NH ₂ , NHCO (C ₁ -C ₄ alkyl), NHCO Substitution of (C ₂ -C ₄ alkenyl), NHCO (C ₂ -C ₄ alkynyl), NHCO phenyl, and phenyl groups.

Even more preferably, R ⁸ and R ⁹ each independently represent hydrogen, halogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₃ -C ₄ alkenyloxy, C ₃ -C ₄ alkynyloxy, C ₁ -C ₄ alkoxycarbonyl, C ₃ -C ₆ cycloalkyl, CONH ₂ , CONH (C ₁ -C ₄ alkyl), CON(C ₁ -C ₄ alkyl) ₂ , NH ₂ , NHCO (C ₁ -C ₄ alkyl), NHCO (C ₂ -C ₄ alkenyl), NHCO (C _2- C ₄ alkynyl), NHCO phenyl, CHN-OH, phenyl or a 5-membered heterocyclic ring containing two or four heteroatoms independently selected from O and N (conditions are: the heterocyclic ring is not Included contiguous oxygen atoms), wherein the alkyl group is optionally independently selected from halo, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C via one or more ₄ alkoxy, benzyloxy, NH ₂ , NHCO (C ₁ -C ₄ alkyl), NHCO (C ₂ -C ₄ alkenyl), NHCO (C ₂ -C ₄ alkynyl), NHCO phenyl and benzene The group of the group is substituted and wherein the heterocyclic ring is substituted with one or more C ₁ -C ₄ alkyl groups.

More preferably, R ⁸ and R ⁹ each independently represent hydrogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₁ -C ₄ alkoxy, C _3- C ₄ alkenyloxy, C ₁ -C ₄ alkoxycarbonyl, CONH ₂ , CONH(C ₁ -C ₄ alkyl), CON(C ₁ -C ₄ alkyl) ₂ , NH ₂ , NHCO (C _1- C ₄ alkyl), NHCO (C ₂ -C ₄ alkenyl), NHCO (C ₂ -C ₄ alkynyl), NHCO phenyl, CHN-OH, phenyl, tetrazolyl or dioxane An alkenyl group, wherein the alkyl group is optionally independently selected from one or more of the group consisting of halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ Alkoxy, benzyloxy, NH ₂ , NHCO (C ₁ -C ₄ alkyl), NHCO (C ₂ -C ₄ alkenyl), NHCO (C ₂ -C ₄ alkynyl), NHCO phenyl, and phenyl The group is substituted and wherein the tetrazolyl group is optionally substituted with a C ₁ -C ₄ alkyl group.

More preferably, R ⁸ and R ⁹ each independently represent hydrogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₁ -C ₄ alkoxy, C _3- C ₄ alkenyloxy, C ₁ -C ₄ alkoxycarbonyl, CONH ₂ , CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl group may optionally be subjected to one or more Substituted independently of a group selected from the group consisting of OH, C ₁ -C ₄ alkoxy, benzyloxy, NH ₂ , NHCO phenyl, and phenyl and wherein the tetrazolyl group may optionally be C ₁ -C ₄ alkyl Replace.

Most preferably, R ⁸ and R ⁹ each independently represent hydrogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₄ alkenyloxy, C ₁ -C ₄ alkoxycarbonyl, CHN-OH, or dioxolyl, wherein the alkyl group is optionally independently selected from OH, CN, C ₁ -C ₄ alkyl via one or more a group substituted with a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₄ alkoxy group, a benzyloxy group, and a phenyl group.

In one group of compounds, R ⁸ and R ⁹ each independently represent hydrogen, halogen, CN, OH, SH, CHO, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkenyl, C ₁ -C ₆ alkyne , C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkenyloxy, C ₁ -C ₆ alkynyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkoxycarbonyl, C ₃ a C ₆ cycloalkyl group, a phenyl group or a 5- or 6-membered heterocyclic ring containing one to three hetero atoms independently selected from O, S and N (provided that the heterocyclic ring does not contain contiguous oxygen atoms, or a sulfur atom adjacent to the adjacent sulfur and oxygen atoms), wherein the alkyl, alkenyl, alkynyl, phenyl and heterocycle may be optionally substituted with one or more groups independently selected from halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, and C ₁ -C ₄ haloalkylthio The group is substituted; or R8 and R9 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. Examples of the heterocyclic ring include dioxolane, dithiolan, Lolinyl, pyrrolidinyl, piperidinyl, piperidine A pyridyl group, a pyrrolyl group, an imidazolyl group or a triazolyl group (for example, 1,2,4triazolyl), more preferably a dioxolane, a dithiolane, a pyridyl group or an imidazolyl group.

Preferably, R ⁸ and R ⁹ each independently represent hydrogen, halogen, CN, OH, SH, CHO, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkenyl , C ₁ -C ₆ haloalkenyl, C ₁ -C ₆ alkynyl, C ₁ -C ₆ haloalkynyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ - C ₆ alkenyloxy, C ₁ -C ₆ haloalkenyloxy, C ₁ -C ₆ alkynyloxy, C ₁ -C ₆ haloalkynyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ haloalkoxycarbonyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl or phenyl, wherein The phenyl group may be optionally independently selected from halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkane by one or more The group of the oxy group is substituted; or R ⁸ and R ⁹ 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, R ⁸ and R ⁹ each independently represent hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ a C ₄ alkenyloxy group or a phenyl group, wherein the phenyl group may be optionally substituted by one or more groups, for example one to five groups, independently selected from the group consisting of halogen, CN, methyl, halomethyl, a methoxy group and a halogenated methoxy group; or R ⁸ and R ⁹ 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 group.

More preferably, R ⁸ and R ⁹ each independently represent hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkenoxy or C ₁ -C ₄ haloalkyl; or R ⁸ and R ⁹ 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.

In one group of compounds, R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ independently of one another represent hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or phenyl, wherein benzene The group may optionally be selected from one or more independently selected from the group consisting 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 group of the group is substituted; or R ⁸ and R ⁹ 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.

R ¹⁰ and R ¹¹ each independently represent hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₁ -C ₄ haloalkyl or phenyl, wherein phenyl is optional Optionally substituted with one or more groups, for example one to five groups, independently selected from halo, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy And a C ₁ -C ₄ haloalkoxy group.

Preferably, R ¹⁰ and R ¹¹ each independently represent hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or phenyl, wherein the phenyl group is optionally Substituted by one or more groups, for example one to five groups, are independently selected from the group consisting of halogen, CN, methyl, halomethyl, methoxy and halomethoxy.

R ¹² and R ^{12 '} independently of each other represent 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 ² O)carbonyl (C ₁ -C ₄ alkyl) Or a phenyl or pyridyl group, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and pyridyl groups are optionally substituted by one or more groups, for example one to five groups, independently Selected from halogen, CN, NH ₂ , NH-C ₁ -C ₈ alkyl, N(C ₁ -C ₈ alkyl) ₂ , NO ₂ , OR ² , C ₁ -C ₄ alkyl, C ₁ -C ₄ a 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 contain contiguous oxygen An atom, an adjacent sulfur atom or an adjacent sulfur and oxygen atom). The heterocyclic ring is preferably one as defined herein, for example Lolinyl, pyrrolidinyl, piperidinyl, piperidine More preferably, pyridyl, pyrrolyl, imidazolyl or triazolyl (eg 1,2,4 triazolyl), more preferably A phenyl group, a pyrrolidinyl group, a pyridyl group or an imidazolyl group.

Preferably, R ¹² and R ^12' independently of each other represent 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 ² O)carbonyl (C ₁ -C ₄ alkyl), wherein the alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, and pyridyl groups are optionally subjected to one or Substituted by a plurality of groups, for example one to five groups, independently selected from halogen, CN, OR ² , 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, and pyridyl.

More preferably, R ¹² and R ^12' independently of each other represent hydrogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, phenyl or pyridyl, wherein the alkyl, alkenyl, phenyl and The pyridyl group may be optionally substituted with one or more groups, for example one to five groups, independently selected from the group consisting of 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 haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy and C ₃ -C ₆ cycloalkyl

More preferably, R ¹² and R ^12' independently represent hydrogen and C ₁ -C ₄ alkyl.

Most preferably, R ¹² and R ^12' independently of each other represent a C ₁ -C ₄ alkyl group.

In one group of compounds, R ¹² and R ^{12 '} independently of each other represent hydrogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, phenyl or pyridyl, wherein the alkyl, alkenyl, phenyl And the pyridyl group may be optionally substituted by one or more groups, for example 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.

Preferably, in the group of compounds, R ¹² and R ^12' independently of each other represent hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, phenyl or pyridin-2-yl, wherein Phenyl and pyridin-2-yl may be optionally substituted by one or more groups, for example one to five groups, independently selected from halo, CN, methyl, halomethyl, methoxy and halo. Methoxy.

R ¹³ and R ^13' independently of each other represent hydrogen, C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl, benzyl, phenyl Or pyridyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and pyridyl groups are optionally substituted by one or more groups, for example one to five groups, independently selected 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 ₄ haloalkoxy.

Preferably, R ¹³ and R ^13' independently of each other represent hydrogen, C ₁ -C ₈ alkyl, C ₁ -C ₈ haloalkyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ halo ring An alkyl group, a C ₃ -C ₈ alkenyl group, a C ₃ -C ₈ haloalkenyl group, a C ₃ -C ₈ alkynyl group, a C ₃ -C ₈ haloalkynyl group, a benzyl group or a pyridyl group, wherein the benzyl group and The pyridyl group may be optionally substituted by one or more groups, for example 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.

More preferably, R ¹³ and R ^13' independently of each other represent C ₁ -C ₄ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl or benzyl, wherein the alkyl, alkenyl, The alkynyl group and the benzyl group may be optionally substituted by one or more groups, for example one to five groups, independently selected from the group consisting of halogen, CN, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy. .

More preferably, R ¹³ and R ^13' independently of each other represent hydrogen, C ₁ -C ₈ alkyl, or C ₁ -C ₈ haloalkyl.

Even more preferably, R ¹³ and R ^13' independently of each other represent hydrogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl.

More preferably, R ¹³ and R ^{13 '} independently of each other represent hydrogen or C ₁ -C ₄ alkyl.

Most preferably, R ¹³ and R ^13' independently of each other represent a C ₁ -C ₄ alkyl group.

In one group of compounds, R ¹³ and R ^{13 '} independently of each other represent hydrogen, C ₁ -C ₄ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl or benzyl, wherein the alkyl group, Alkenyl, alkynyl and benzyl may be optionally substituted by one or more groups, for example one to five groups, independently selected from C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, halogen, CN, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy.

More preferably, in this group of compounds, R ¹³ and R ^13' independently of each other represent hydrogen, C ₁ -C ₄ alkyl or C ₃ -C ₆ alkynyl.

Most preferably, in this group of compounds, R ¹³ and R ^{13 '} independently of each other represent hydrogen, methyl or propargyl.

R ¹⁴ and R ¹⁵ each independently represent hydrogen, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy, preferably It is hydrogen, halogen, methyl, halomethyl, methoxy or halomethoxy.

R ¹⁶ represents hydrogen, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₆ cycloalkyl, C ₁ -C ₈ alkylcarbonyl or C ₁ -C ₈ haloalkylcarbonyl Preferred are hydrogen, halogen, methyl, halomethyl, methoxy or halomethoxy.

In one group of compounds, no more than one of N ¹ , L ^{5 ,} and L ² , and no more than one N of L ³ , L ^{6 ,} and L ⁴ .

In one group of compounds, L ¹ is CD ¹ , L ² is CD ² and L ⁵ is CD ⁵ .

In one group of compounds, L ¹ is CD ¹ , L ² is CD ² , L ³ is CD ³ , L ⁴ is CD ⁴ , L ⁵ is CD ⁵ and L ⁶ is CD ⁶ .

In one group of compounds, L ¹ is CD ¹ , L ² is N and L ⁵ is CD ⁵ .

In one group of compounds, L ¹ is CD ¹ , L ² and L ³ is N, L ⁴ is CD ⁴ , L ⁵ is CD ⁵ and L ⁶ is CD ⁶ .

In one group of compounds, L ¹ is N, L ² is CD ² and L ⁵ is CD ⁵ .

In one group of compounds, L ¹ and L ⁴ are N, L ² is CD ² , L ³ is CD ³ , L ⁵ is CD ⁵ and L ⁶ is CD ⁶ .

In one group of compounds, L ¹ is N or CD ¹ ; L ² is CD ² ; L ³ is CD ³ ; L ⁴ is N or CD ⁴ ; L ⁵ is CD ⁵ ; L ⁶ is CD ⁶ .

In a group of compounds, wherein L ¹ is the same as L ⁴ , L ⁵ is the same as L ⁶ , L ² is the same as L ³ , and Q is the same as Q′.

In one group of compounds, the Q system Q-9 and G ¹ , G ² and G ³ represent a methylene group. In one group of compounds, Q 'based Q-9' and G ^1, G ² and G ³ represents a methylene group. In one group of compounds, Q is Q-9 and Q' is Q-9' and G ¹ , G ² and G ³ represent methylene.

In a group of compounds, L ¹ is N or CD ¹ ; L ² is CD ² ; L ³ is CD ³ ; L ⁴ is N or CD ⁴ ; L ⁵ is CD ⁵ ; L ⁶ is CD ⁶ ; D ¹ , D ² And D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other 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 ³ ) ₂ , phenyl or CO ₂ R ² wherein the alkyl, alkoxy, alkenyloxy, cycloalkyl and phenyl groups may optionally be passed through one or Substituting a plurality of groups independently selected from the group consisting of halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ alkoxy, and C ₁ -C ₄ haloalkoxy; or D ¹ and D ⁵ , D ² and D ⁵ , D ³ and D ⁶ , D ⁴ and D ⁶ together with the ring segments to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring, The ring formed by D ¹ and D ⁵ , D ² and D ⁵ , D ³ and D ⁶ , D ⁴ and D ⁶ may optionally be independently selected from halogen, CN, C ₁ -C ₄ via one or more Substituted by a group of 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; X represents X-3 or X-5; Z ³ , Z ⁵ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ are represented independently of each other CR ⁴ R ⁵ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ , C=O or C=CR ⁶ R ⁷ ; the Q system is selected from the group consisting of Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8, and Q-9; Y ¹ , Y ² , Y ³ , and Y ⁴ each independently 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 ³ ) ₂ , C ₁ -C ₄ alkane Thio group, C ₁ -C ₄ alkylsulfinyl group, C ₁ -C ₄ alkylsulfonyl group, phenyl group, phenoxy group or CO ₂ R ² wherein the alkyl group, alkoxy group, alkenyloxy group And a cycloalkyl group and a phenyl group are optionally independently selected from the group consisting of halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ alkoxy, and a group substituted with a C ₁ -C ₄ haloalkoxy group; when the Q system is Q-1, Q-2, Q-3, Q-4, Q-6, or Q-7, then Y ¹ and Y ² , Y ² and Y ³ , or Y ³ and Y ⁴ independently of each other together with the ring segment to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring, wherein Y ¹ and Y ² , Y The ring formed by ² and Y ³ , or Y ³ and Y ⁴ may be optionally independently selected from halogen, CN, C ₁ -C ₄ alkyl, C by one or more _a group substituted with ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ alkylthio; when Q is Q-1, Q-3, Q -4, Q-7 or Q-8 and L ¹ is CD ¹ , then Y ¹ and D ¹ together with the fragments to which they are attached may form a fully unsaturated 6-membered carbocyclic ring, wherein by D ¹ and The ring formed by Y ¹ may optionally be independently selected from halo, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C _a group substituted with a ₁ -C ₄ haloalkoxy group and a C ₁ -C ₄ alkylthio group; when Q is Q-9 and L ¹ is CD ¹ , then R ¹² and D ¹ may together be -(G ¹ ) _p -G ² -G ³ -; Q' is selected from the group consisting of Q-1', Q-2', Q-3', Q-4', Q-5', Q -6', Q-7', Q-8' and Q-9'; Y ^{1 '} , Y ^{2 '} , Y ^3' , Y ^4' each independently 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 ³ ) ₂ , C ₁ -C ₄ alkylthio, C ₁ alkylsulfinyl -C ₄ acyl, C ₁ -C ₄ alkylsulfonyl group, a phenyl group, a phenoxy group, or CO ^₂ R _2, wherein the alkyl, alkoxy, alkenyl group, cycloalkyl group And phenyl optionally substituted with one or more 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 Substituted by a group of ₄ haloalkoxy; when Q' is Q-1', Q-2', Q-3', Q-4', Q-6', or Q-7', then Y ^{1 '} and Y ^{2 '} , Y ^{2 '} and Y ^{3 '} , or Y ^{3 '} and Y ^{4 '} independently of each other together with the ring segment to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring, Rings wherein Y ^{1 '} and Y ^{2 '} , Y ^{2 '} and Y ^{3 '} , or Y ^{3 '} and Y ^{4 '} may be optionally independently selected from halo, CN, C ₁ -C via one or more _a group substituted with a ₄ alkyl group, 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; when Q' is a Q-1 group ', Q-3', Q-4', Q-7' or Q-8' and L ⁴ is CD ⁴ , then Y ^{1 '} and D ⁴ together with the fragments to which they are attached may form fully unsaturated a 6-membered carbocyclic ring wherein the ring formed by D ⁴ and Y ^{1 '} can be optionally selected from one or more independently selected from the group consisting of halogen, CN, 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 groups taken ; When Q 'line Q-9' and the line L ⁴ CD ^4, the R ^{12 'D 4} may be together with the _{^{- (G 1) p -G 2}} -G 3 -; G 1, G 2 and G ³ represents C(R ²¹ ) ₂ ; each p independently of 1 or 2; each R ² independently of one another represents hydrogen, C ₁ -C ₈ alkyl, C ₁ -C ₈ haloalkyl, C ₃ -C ₈ olefin a C ₃ -C ₈ haloalkenyl group, a C ₃ -C ₈ haloalkynyl group, a phenyl group, a benzyl group or a pyridyl group, wherein the phenyl group, the benzyl group and the pyridyl group are optionally one or more Independently 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, and C ₁ -C ₄ haloalkoxy Substituted; each R ³ independently of one another represents hydrogen or C ₁ -C ₄ alkyl; wherein when two groups R ^{3 are} attached to the same nitrogen atom, the groups may be the same or different And wherein when two groups R ^{3 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 optionally substituted with one or more groups independently selected from halogen, methyl or halomethyl; each of R ⁴ and R ⁵ Representing independently of each other hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkenoxy or C ₁ -C ₄ haloalkyl; or R ⁴ And R ⁵ 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; R ⁶ and R ⁷ each independently represent hydrogen , halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl; R ⁸ and R ⁹ each independently represent hydrogen, halogen, CN, OH, SH, CHO, C ₁ -C ₆ alkyl, C _1- C ₆ haloalkyl, C ₁ -C ₆ alkenyl, C ₁ -C ₆ haloalkenyl, C ₁ -C ₆ alkynyl, C ₁ -C ₆ haloalkynyl, C ₁ -C ₆ alkoxy , C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkenyloxy, C ₁ -C ₆ haloalkenyloxy, C ₁ -C ₆ alkynyloxy, C ₁ -C ₆ haloalkynyloxy , C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ haloalkoxycarbonyl, C ₃ -C ₆ cycloalkyl, C ₃ a -C ₆ halocycloalkyl or phenyl group, wherein the phenyl group is optionally independently selected from halo, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy groups Substituted; or R ⁸ and R ⁹ together with the carbon atoms they are attached to form thereon a C ₃ -C ₆ cycloalkyl group or halogenated C ₃ -C ₆ cycloalkyl group together; R ¹² and R ^{12 '} Independently from each other represents hydrogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, phenyl or pyridyl, wherein the alkyl, alkenyl, phenyl and pyridyl groups may optionally be passed through one or more Independently selected 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 haloalkyl a group substituted with a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ haloalkoxy group, and a C ₃ -C ₆ cycloalkyl group; R ¹³ and R ^13' independently of each other represent a C ₁ -C ₄ alkyl group, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl or benzyl, wherein the alkyl, alkenyl, alkynyl and benzyl are optionally independently selected from halo, CN, C via one or more Substituted with a group of ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy; each R ²¹ independently of one another represents hydrogen, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy.

In a group of compounds, L ¹ is N or CD ¹ ; L ² is CD ² ; L ³ is CD ³ ; L ⁴ is N or CD ⁴ ; L ⁵ is CD ⁵ ; L ⁶ is CD ⁶ ; D ¹ , D ² And D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other represent hydrogen, C ₁ -C ₄ alkyl, CN or C ₁ -C ₄ alkoxy, wherein the alkyl and alkoxy groups may optionally be One or more groups independently selected from the group consisting of halogen, CN, C ₁ -C ₄ alkoxy, and C ₁ -C ₄ haloalkoxy; X represents X-3 or X-5; Z ³ , Z ⁵ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ independently of each other represent CR ⁴ R ⁵ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ , C=O or C=CR ⁶ R ⁷ ; the Q system is selected from the group consisting of The group consists of: Q-1, Q-2, Q-3, and Q-9; Y ¹ , Y ² , Y ^{3 ,} and Y ⁴ each independently represent hydrogen, C ₁ -C ₄ alkyl, CN Or a C ₁ -C ₄ alkoxy group, wherein the alkyl group and the alkoxy group are optionally independently selected from halo, CN, C ₁ -C ₄ alkoxy, and C ₁ -C ₄ haloalkane by one or more a group of oxy groups; when Q is Q-1, Q-2 or Q-3, then Y ² and Y ³ together with the fragments to which they are attached may form a fully unsaturated 6-membered carbocyclic ring and wherein the ring formed by Y ² and Y ³ may be Optionally substituted with 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 and C a group substituted with a ₁ -C ₄ alkylthio group; when the Q system is Q-1 or Q-3, then Y ¹ and D ¹ together with the fragments to which they are attached may form a fully unsaturated 6-membered carbocyclic ring. And wherein the ring formed by D ¹ and Y ¹ is optionally independently selected from halo, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkane a group substituted with an oxy group, a C ₁ -C ₄ haloalkoxy group, and a C ₁ -C ₄ alkylthio group; when Q is Q-9 and L ¹ is CD ¹ , then R ¹² and D ¹ may together be -( G ¹ ) _p -G ² -G ³ -; Q' is selected from the group consisting of Q-1', Q-2', Q-3' and Q-9'; Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently represent hydrogen, C ₁ -C ₄ alkyl, CN or C ₁ -C ₄ alkoxy, wherein the alkyl and alkoxy are optional Substituted by one or more groups independently selected from the group consisting of halogen, CN, C ₁ -C ₄ alkoxy, and C ₁ -C ₄ haloalkoxy; when Q' is Q-1', Q-2' or At Q-3', then Y ^{2 '} and Y ^{3 '} together with the one to which they are attached The fragment may form a fully unsaturated 6-membered carbocyclic ring and wherein the ring formed by Y ^{2 '} and Y ^{3 '} may be optionally selected from one or more independently selected from the group consisting of halogen, CN, C ₁ -C ₄ alkyl, Group substitution of C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ alkylthio; when Q' is Q-1' or Q- At 3', then Y ^{1 '} and D ⁴ together with the fragments to which they are attached may form a fully unsaturated 6-membered carbocyclic ring or wherein the ring formed by D ⁴ and Y ^{1 '} may optionally pass through a Or a plurality selected independently from halogen, CN, 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 Substituted with alkylthio group; when Q' is Q-9' and L ⁴ is CD ⁴ , then R ^12' and D ⁴ may together be -(G ¹ ) _p -G ² -G ³ -; G ¹ , G ² and G ³ each independently represent -C(R ¹⁴ R ¹⁵ )-; each p-system 1; R ⁴ and R ⁵ each independently represent hydrogen, halogen, CN, OH, C ₁ -C ₄ C ₁ -C ₄ alkyl or haloalkyl; R ⁶ and R ⁷ each independently represent hydrogen, halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl, each other; R ⁸ and R ⁹ are each independently Represents hydrogen, halogen, CN, OH, SH, CHO , C 1 -C 6 alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkenyl, C ₁ -C ₆ haloalkenyl group, C ₁ - C ₆ alkynyl, C ₁ -C ₆ haloalkynyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkenyloxy, C ₁ -C ₆ haloolefin Oxyl, C ₁ -C ₆ alkynyloxy, C ₁ -C ₆ haloalkynyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkoxycarbonyl a C ₁ -C ₆ haloalkoxycarbonyl group, a C ₃ -C ₆ cycloalkyl group, a C ₃ -C ₆ halocycloalkyl group or a phenyl group, wherein the phenyl group may be optionally independently selected by one or more Substituted from a group of halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy; or R ⁸ and R ⁹ together they are attached to a carbon atom which forms C3-C ₆ cycloalkyl group or halogenated C ₃ -C ₆ cycloalkyl group together; R ¹² and R ^{12 'independently} of one another represent hydrogen, C ₁ -C _{a 4-} alkyl, C ₂ -C ₄ alkenyl, phenyl or pyridyl group, wherein the alkyl, alkenyl, phenyl and pyridyl groups are optionally substituted by one or more groups, for example 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; R ¹³ and R ^{13 '} independently of each other represent hydrogen, C ₁ -C ₈ alkane Or a C ₁ -C ₈ haloalkyl group; R ¹⁴ and R ¹⁵ each independently represent hydrogen, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy.

In a group of compounds, L ¹ is N or CD ¹ ; L ² is CD ² ; L ³ is CD ³ ; L ⁴ is N or CD ⁴ ; L ⁵ is CD ⁵ ; L ⁶ is CD ⁶ ; D ¹ , D ² And D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other 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 ³ ) ₂ , phenyl or CO ₂ R ² wherein the alkyl, alkoxy, alkenyloxy, cycloalkyl and phenyl groups may optionally be passed through one or Substituting a plurality of groups independently selected from the group consisting of halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ alkoxy, and C ₁ -C ₄ haloalkoxy; or D ¹ and D ⁵ , D ² and D ⁵ , D ³ and D ⁶ , D ⁴ and D ⁶ together with the ring segments to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring, The ring formed by D ¹ and D ⁵ , D ² and D ⁵ , D ³ and D ⁶ , D ⁴ and D ⁶ may optionally be independently selected from halogen, CN, C ₁ -C ₄ via one or more Substituted by a group of 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.

X represents X-3 or X-5; Z ³ , Z ⁵ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ independently of each other represent CR ⁴ R ⁵ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ , C=O Or C=CR ⁶ R ⁷ ; Q is selected from the group consisting of Q-1, Q-2, Q-4, Q-5, Q-6, Q-7, Q-8 And Q-9; Y ¹ , Y ² , Y ³ , Y ⁴ each independently 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 ³ ) ₂ , C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonate An anthracenyl, phenyl, phenoxy or CO ₂ R ² wherein the alkyl, alkoxy, alkenyloxy, cycloalkyl and phenyl groups are optionally independently selected from halo, CN by one or more a group substituted with a C ₁ -C ₄ 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 the Q system is Q-1, Q-2 , Q-4, Q-6, or Q-7, then Y ¹ and Y ² , Y ² and Y ³ , or Y ³ and Y ⁴ independently of each other together with the ring segment to which they are attached may form part or fully unsaturated 5- to 7-membered carbocyclic ring, wherein the ring formed by Y ¹ and Y ^2, Y ² and Y ^3, or Y ³ and Y ⁴ Optionally substituted with 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, and a group substituted with a C ₁ -C ₄ alkylthio group; when the Q system is Q-1, Q-4, Q-7 or Q-8 and the L ¹ is CD ¹ , then Y ¹ and D ¹ are attached thereto along with The fragment thereon may form a fully unsaturated 6-membered carbocyclic ring wherein the ring formed by D ¹ and Y ¹ may be optionally independently selected from halogen, CN, OH, C ₁ -C ₄ via one or more a group substituted with an alkyl group, 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; when the Q system is Q-9 and L ^{When 1} is CD ¹ , then R ¹² and D ¹ may together be -(G ¹ ) _p -G ² -G ³ -; Q' is selected from the group consisting of: Q-1', Q-2', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9'; Y ^1' , Y ^2' , Y ^3' , Y ^4' Each independently 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 ³ ) ₂ , C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, phenyl, phenoxy or CO ₂ R ² , wherein the alkyl, alkoxy, alkenyloxy, cycloalkyl and phenyl groups are optionally independently selected from halo, CN, C ₁ -C ₄ alkyl, C ₁ - Group substitution of C ₄ -haloalkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy; when Q' is Q-1', Q-2', Q-4', Q-6 ', or Q-7', then Y ^{1 '} and Y ^{2 '} , Y ^{2 '} and Y ^{3 '} , or Y ^{3 '} and Y ^{4 '} independently of each other together with the ring segment to which they are attached may form part Or a fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by Y ^{1 '} and Y ^{2 '} , Y ^{2 '} and Y ^{3 '} , or Y ^{3 '} and Y ^{4 '} may optionally be passed through one or A plurality of independently 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, and C ₁ -C ₄ alkane Thio group substitution; when Q' is Q-1', Q-4', Q-7' or Q-8' and L ⁴ is CD ⁴ , then Y ^{1 '} and D ⁴ are attached to them together The fragment thereon may form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D ⁴ and Y ^{1 '} may be optionally independently selected from halogen, CN, OH, C ₁ -C via one or more ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkyl Group and a C ₁ -C ₄ alkylthio groups; when Q 'line Q-9' and L ⁴ based upon CD ^4, the R ^{12 'D 4} may be together with the - (G ¹⁾ _p -G ² -G ³ -; G ¹ , G ² and G ³ represent C(R ²¹ ) ₂ ; each p independently represents 1 or 2; each R ² independently of one another 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, phenyl, benzyl or pyridyl, wherein the phenyl And benzyl and pyridyl are optionally independently selected from halo, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ -haloalkyl, C ₁ Substituted with a C ₄ alkoxy group and a C ₁ -C ₄ haloalkoxy group; each R ³ independently of one another represents hydrogen or C ₁ -C ₄ alkyl; wherein when two groups R ^{3 are} attached to the same When on a nitrogen atom, the groups may be the same or different; and wherein when two groups R ^{3 are} attached to the same nitrogen atom, the two groups together with the nitrogen atom to which they are attached Rings B-1, B-2, B-3, B-4 or B-5 may be formed wherein the ring formed may optionally be selected from one or more independently selected from halo, methyl or Substituted by a halogenated methyl group; R ⁴ and R ⁵ each independently represent hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ olefin Oxyl or C ₁ -C ₄ haloalkyl; or R ⁴ and R ⁵ 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 a group; R ⁶ and R ⁷ each independently represent hydrogen, halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl; and R ⁸ and R ⁹ each independently represent hydrogen, halogen, CN, OH. , SH, CHO, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkenyl, C ₁ -C ₆ haloalkenyl, C ₁ -C ₆ alkynyl, C ₁ - C ₆ haloalkynyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkenyloxy, C ₁ -C ₆ haloalkenyloxy, C ₁ -C ₆ Alkynyloxy, C ₁ -C ₆ haloalkynyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ haloalkoxy A carbonyl group, a C ₃ -C ₆ cycloalkyl group, a C ₃ -C ₆ halocycloalkyl group or a phenyl group, wherein the phenyl group is optionally independently selected from halogen, CN, C ₁ - C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ Substituting a group of -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy; or R ⁸ and R ⁹ together with the carbon atom to which they are attached form a C ₃ -C ₆ cycloalkyl group or C _{a 3-} C ₆ halocycloalkyl group; R ¹² and R ^{12 '} independently of each other represent hydrogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, phenyl or pyridyl, wherein the alkyl The alkenyl, phenyl, and pyridyl groups are optionally independently selected from halo, CN, OH, NH ₂ , NH-C ₁ -C ₄ alkyl, N(C ₁ -C ₄ alkyl) via one or more ) _2, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl group, a substituted C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy and C ₃ -C ₆ cycloalkyl group group; R ¹³ and R ^{13 '} independently of each other represent a C ₁ -C ₄ alkyl group, a C ₃ -C ₆ alkenyl group, a C ₃ -C ₆ alkynyl group or a benzyl group, wherein the alkyl group, the alkenyl group, the alkynyl group and the benzyl group Optionally substituted with one or more groups independently selected from the group consisting of halogen, CN, C ₁ -C ₄ alkoxy, and C ₁ -C ₄ haloalkoxy; each R ²¹ independently of one another represents hydrogen, halo C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy.

In one group of compounds, L ¹ is N or CD ¹ ; L ² is CD ² ; L ³ is CD ³ ; L ⁴ is N or CD ⁴ ; L ⁵ is CD ⁵ ; L ⁶ is CD ⁶ ; D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other represent hydrogen, C ₁ -C ₄ alkyl, CN or C ₁ -C ₄ alkoxy, wherein the alkyl and alkoxy are optionally Substituted by one or more groups independently selected from the group consisting of halogen, CN, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy; X represents X-3 or X-5; Z ³ , Z ⁵ Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ independently of each other represent CR ⁴ R ⁵ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ , C=O or C=CR ⁶ R ⁷ ; the Q system is selected from the group consisting of The group consists of: Q-1, Q-2, and Q-9; Y ¹ , Y ² , Y ^{3 ,} and Y ⁴ each independently represent hydrogen, C ₁ -C ₄ alkyl, CN or C ₁ a -C ₄ alkoxy group, wherein the alkyl group and the alkoxy group are optionally optionally one or more selected from the group consisting of halogen, CN, C ₁ -C ₄ alkoxy, and C ₁ -C ₄ haloalkoxy a group substitution; when the Q system is Q-1 or Q-2, then Y ² and Y ³ together with the fragments to which they are attached may form a fully unsaturated 6-membered carbocyclic ring and wherein Y ² and Y ^{3 are} The formed ring can optionally One or more 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 and C ₁ -C _a group of ₄ alkylthio groups; when Q is Q-1, then Y ¹ and D ¹ together with the fragments to which they are attached may form a fully unsaturated 6-membered carbocyclic ring and wherein D ¹ and Y The ring formed by ¹ may optionally be selected from one or more independently 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 Substituted by a _4- haloalkoxy group and a C ₁ -C ₄ alkylthio group; when Q is Q-9 and L ¹ is CD ¹ , then R ¹² and D ¹ may together be -(G ¹ ) _p -G ² -G ³ -; Q' is selected from the group consisting of Q-1', Q-2', and Q-9'; Y ^{1 '} , Y ^2' , Y ^3', and Y ^{4 '} each independently of each other represents hydrogen, C ₁ -C ₄ alkyl, CN or C ₁ -C ₄ alkoxy, wherein the alkyl and alkoxy are optionally independently selected from halogen, by one or more Substitution of CN, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy; when Q' is Q-1' or Q-2', Y ^{2 '} and Y ^3' together with The segment connected to it can form no at all 6-membered ring and wherein the carbocyclic ring and Y ^{2 'and} Y ^3' may be formed optionally substituted with one or more groups independently selected from halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ a haloalkyl group, a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ haloalkoxy group, and a C ₁ -C ₄ alkylthio group; when Q' is Q-1', then Y ^{1 '} and D ⁴ together with the fragments to which they are attached may form a fully unsaturated 6-membered carbocyclic ring or and wherein the ring formed by D ⁴ and Y ^{1 '} may optionally be independently selected from halogen, CN by one or more a group substituted with a C ₁ -C ₄ alkyl group, 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; When 'Q-9' and L ⁴ is CD ⁴ , then R ^{12 '} and D ⁴ may together be -(G ¹ ) _p -G ² -G ³ -; G ¹ , G ² and G ³ are each independently of each other Represents -C(R ¹⁴ R ¹⁵ )-; each p is 1; R ⁴ and R ⁵ each independently represent hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl R ⁶ and R ⁷ each independently represent hydrogen, halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl; R ⁸ and R ⁹ each independently represent hydrogen, halogen, CN, OH, SH. , C HO, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkenyl, C ₁ -C ₆ haloalkenyl, C ₁ -C ₆ alkynyl, C ₁ -C ₆ halo Alkynyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy, C ₁ -C ₆ alkenyloxy, C ₁ -C ₆ haloalkenyloxy, C ₁ -C ₆ alkynyloxy , C ₁ -C ₆ haloalkynyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₁ -C ₆ alkoxycarbonyl, C ₁ -C ₆ haloalkoxycarbonyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ halocycloalkyl or phenyl, wherein the phenyl group is optionally independently selected from halo, CN, C ₁ -C ₄ alkane by one or more a group of a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ haloalkoxy group; or R ⁸ and R ⁹ together with the carbon atom to which they are attached a C ₃ -C ₆ cycloalkyl group or a C ₃ -C ₆ halocycloalkyl group; R ¹² and R ^12' independently of each other represent hydrogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ olefin Or a phenyl or pyridyl group, wherein the alkyl, alkenyl, phenyl and pyridyl groups are optionally substituted by one or more groups, for example 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 group; R ¹³ and R ^{13 'independently} of one another represent hydrogen, C ₁ -C ₈ alkyl, or C ₁ -C ₈ haloalkyl; R ¹⁴ and R ¹⁵ each independently represents hydrogen, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy.

In another group of compounds, D ¹ , D ² , D ³ and D ⁴ independently of each other represent hydrogen, C ₁ -C ₄ alkyl, CN or C ₁ -C ₄ alkoxy, wherein the alkyl and alkoxy The group may be optionally substituted by one or more groups, for example one to five groups, independently selected from the group consisting of halogen, CN, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy; D ⁵ and D ⁶ independently of each other represents 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 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 contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and An oxygen atom, for example a heterocyclic ring as defined herein, preferably a furyl, thiophenyl or pyrazolyl), COR ¹ , OR ² , SH, a C ₁ -C ₈ alkylthio group, a C ₁ -C ₈ Alkylsulfinyl, C ₁ -C ₈ alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, N(R ³ ) ₂ , CO ₂ R ² , O (CO ^{) R 1, CON (R 3} ) 2, NR 3 COR 1 or CR ¹ N-oR ^2, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and heterocycle may be Optionally substituted with one or more groups, for example one to five groups independently selected from _{halogen, CN, NH 2, NO 2} , OR 2, C 1 -C 4 alkyl and C ₁ -C ₄ haloalkyl, X represents X-3, X-4 or X-5; Z ³ , Z ⁵ , Z ⁶ , Z ⁷ , Z ⁸ , Z ⁹ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ independently represent CR ⁴ R ⁵ or C=CR ⁶ R ⁷ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ , SiR ¹⁰ R ¹¹ , C=O or C=CR ⁶ R ⁷ ; the Q system is selected from the group consisting of the following Composition: Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and Q-9; Q' is selected from the group consisting of the following Composition: Q-1', Q-2', Q-3', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9'; Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently represent hydrogen, halogen, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ An alkoxy group or a phenyl group, wherein the phenyl group may be optionally substituted by one or more groups, for example 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; when Q is Q-1, Q-2, Q-3, Q-4, Q-6 or Q-7 When Y ¹ and Y ² , Y ² and Y ³ , or Y ³ and Y ⁴ independently of each other together with the ring segments to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or comprise one to three independently selected a 5- to 7-membered heterocyclic ring of a hetero atom from N and N(R ³ ), and wherein a ring formed by Y ¹ and Y ² , Y ² and Y ³ , or Y ³ and Y ⁴ may optionally be One or more independently 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, C ₁ -C ₄ Substituted with haloalkoxy and C ₁ -C ₄ alkylthio; when Q' is Q-1', Q-2', Q-3', Q-4', Q-6' or Q-7' When Y ^{1 '} and Y ^{2 '} , Y ^{2 '} and Y ^{3 '} , or Y ^{3 '} and Y ^{4 '} independently of each other together with the ring segment to which they are attached may form a partially or fully unsaturated 5- to a 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R ³ ), and wherein Y ^{1 '} and Y ^{2 '} , Y ^{2 '} and Y The ring formed by ^3' or Y ^{3 '} and Y ^4' may be optionally independently selected from halo, 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 halogenated Alkoxy and C ₁ -C ₄ alkylthio group substitution; when Q is Q-1, Q-3, Q-4, Q-7 or Q-8 and L ¹ is CD ¹ , then Y ¹ And D ¹ together with the fragments to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring, wherein the ring formed by D ¹ and Y ¹ may optionally be subjected to one or more groups Substituted, for example, one to five groups, independently selected from halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkane Oxyl and C ₁ -C ₄ alkylthio; when Q is Q-1', Q-3', Q-4', Q-7' or Q-8' and L ⁴ is CD ⁴ , then Y ¹ 'and D ⁴ together with the fragments to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring, wherein the ring formed by D ¹ and Y ¹ may optionally be through one or more groups a group substituted, for example one to five groups, independently selected from halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ a haloalkoxy group and a C ₁ -C ₄ alkylthio group; when Q is Q-9 and L ¹ is CD ¹ , then R ¹² and D ¹ may together be -(G ¹ ) _p -G ² -G ³ -; when Q 'line Q-9' and the line L ⁴ CD ^4, the R ^{12 'and} D ⁴ may be Together they are -(G ¹ ) _p -G ² -G ³ -; G ¹ , G ² and G ³ represent C(R ²¹ ) ₂ , wherein each R ²¹ independently represents hydrogen, halogen, C ₁ -C _{a 4-} alkyl group, a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₄ alkoxy group or a C ₁ -C ₄ haloalkoxy group; each p independently of each other represents 1 or 2; each R ¹ independently of ^one another represents hydrogen a C ₁ -C ₄ alkyl or phenyl group, wherein the alkyl group and the phenyl group are optionally independently selected from halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, via one or more, Substituted by a C ₁ -C ₄ alkoxy group and a C ₁ -C ₄ haloalkoxy group; each R ² independently of one another represents hydrogen, C ₁ -C ₈ alkyl, C ₁ -C ₈ haloalkyl, C ₃ a -C ₈ alkenyl group, a C ₃ -C ₈ haloalkenyl group, a C ₃ -C ₈ haloalkynyl group, a phenyl group, a benzyl group or a pyridyl group, wherein the phenyl group, the benzyl group and the pyridyl group are optionally One or more independently 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, and C ₁ -C ₄ haloalkoxy groups; each R ³ independently represents hydrogen or C ₁ -C ₄ alkyl each other; wherein when two R ³ groups attached to the same nitrogen atom, the Groups may be the same or different; and wherein when two groups R ³ when attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached to form a ring which may be B-1, B-2, B-3, B-4 or B-5, wherein the ring formed may be optionally substituted by one or more groups, for example one to five groups, independently selected from halo, methyl or Halomethyl; R ⁴ and R ⁵ each independently represent hydrogen, halogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C _1- C ₄ alkoxy, C ₃ -C ₄ alkenyloxy, C ₁ -C ₄ alkoxycarbonyl, C ₃ -C ₆ cycloalkyl, CON(R ³ ) ₂ , NH ₂ , NR ³ COR ¹ Or CR ¹ N-OR ² , wherein the alkyl, alkenyl, alkynyl group is optionally independently selected from halo, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ via one or more Substituted haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy and NH ₂ groups; R ⁶ and R ⁷ each independently represent hydrogen, halo, methyl or halomethyl; ⁸ and R ⁹ each independently represent hydrogen, halogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₃ -C ₄ alkenyloxy, C ₃ -C ₄ alkynyloxy, C ₁ -C ₄ alkoxycarbonyl, C ₃ -C ₆ cycloalkyl, CONH ₂ , CONH(C ₁ -C ₄ alkyl), CON(C ₁ -C ₄ alkyl) ₂ , NH ₂ , NHCO (C ₁ -C ₄ alkyl), NHCO (C ₂ -C ₄ alkenyl), NHCO (C ₂ - C ₄ alkynyl), NHCO phenyl, CHN-OH, phenyl or a 5-membered heterocyclic ring containing two or four heteroatoms independently selected from O and N (provided that the heterocyclic ring does not contain a contiguous Oxygen atom), wherein the alkyl group is optionally independently selected from halo, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkane Oxyl, benzyloxy, NH ₂ , NHCO (C ₁ -C ₄ alkyl), NHCO (C ₂ -C ₄ alkenyl), NHCO (C ₂ -C ₄ alkynyl), NHCO phenyl, and phenyl a group substituted and wherein the heterocyclic ring is substituted by one or more C ₁ -C ₄ alkyl groups; R ¹⁰ and R ¹¹ each independently represent hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or phenyl, wherein the phenyl group may be optionally substituted by one or more groups, for example one to five groups, independently selected from halo, CN, methyl, halomethyl, Methoxy and halogenated methoxy; R ¹² and R ^{12 '} independently of each other represent 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 ² O)carbonyl (C ₁ -C ₄ alkyl), wherein the alkyl, alkenyl, alkynyl, cycloalkyl, phenyl and pyridyl groups are optionally substituted by one or more groups , for example, one to five groups independently selected from halogen, CN, OR ² , NH ₂ , NH-C ₁ -C ₈ alkyl, N(C ₁ -C ₈ alkyl) ₂ , C ₁ -C ₄ alkane a C ₁ -C ₄ haloalkyl group, a C ₃ -C ₆ cycloalkyl group, and a pyridyl group; R ¹³ and R ^{13 '} independently of each other represent a C ₁ -C ₄ alkyl group, a C ₃ -C ₆ alkenyl group, a C ₃ group _; a -C ₆ alkynyl or benzyl group, wherein the alkyl, alkenyl, alkynyl and benzyl group are optionally substituted by one or more groups, for example one to five groups, independently selected from halogen, CN, a C ₁ -C ₄ alkoxy group and a C ₁ -C ₄ haloalkoxy group; in another group of compounds, D ¹ , D ² , D ³ and D ⁴ independently of each other represent hydrogen, C ₁ -C ₄ alkyl, CN or C ₁ -C ₄ alkoxy; D ⁵ and D ⁶ independently of each other represent hydrogen, C ₁ -C ₄ alkyl, phenyl, containing one to three heterogenes independently selected from O, S and N a 5-membered heterocyclic ring (provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms), wherein the phenyl group and the heterocyclic ring may optionally be subjected to one or more Substituents independently selected from the group consisting of halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl, and C ₁ -C ₄ haloalkyl.

X represents X-3 or X-5; Z ³ , Z ⁵ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ independently of each other represent CR ⁴ R ⁵ or C=CR ⁶ R ⁷ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ or C=CR ⁶ R ⁷ ; Q is selected from the group consisting of Q-1, Q2, Q-3 and Q-9; Q' is selected from the group consisting of the group It consists of: Q-1', Q2', Q-3', and Q-9'; Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently of each other represents hydrogen, halogen, OH, C ₁ -C ₄ alkyl or phenyl, wherein the phenyl group may optionally be bonded via one or more groups independently selected from C ₁ -C ₄ alkyl Substituting; each group of Y ² and Y ³ together with the ring segments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by Y ² and Y ³ may optionally be subjected to one or A plurality of independently 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, and C ₁ -C ₄ alkane Thio group substitution; each group Y ^{2 '} and Y ^{3 '} together with the ring segment to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring, wherein Y ^{2 '} and Y ^{3 ' are} formed Ring can optionally Or more 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 and C ₁ -C ₄ a group substituted with an alkylthio group; when the Q system is Q-1, Q-3, Q-4, Q-7 or Q-8 and the L ¹ is CD ¹ , then Y ¹ and D ¹ are attached thereto along with The above fragment may form a fully unsaturated 6-membered carbocyclic ring wherein the ring formed by D ¹ and Y ¹ may be optionally substituted with one or more groups, for example one or two groups, independently selected from Halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy; when Q' is Q-1', Q-3', Q-4', Q-7' or Q- 8 and L ⁴ is CD ⁴ , then Y ¹ 'and D ⁴ together with the fragments to which they are attached may form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D ⁴ and Y ^{1 '} Optionally substituted with one or more groups, such as one or two groups, independently selected from the group consisting of halogen, CN, OH, methyl, halomethyl, methoxy, and halomethoxy; When Q-9 and L ¹ are CD ¹ , then R ¹² and D ¹ may together be -(G ¹ ) _p -G ² -G ³ -; when Q' is Q-9' and L ⁴ is CD ⁴ , Then R ^12' and D ⁴ can be together - (G ¹ _p -G ² -G ³ -; G ¹ , G ² and G ³ represent C(R ²¹ ) ₂ ; each R ²¹ independently of one another represents hydrogen or C ₁ -C ₄ alkyl; each p is independently of each other Represents 1 or 2; R ⁴ and R ⁵ each independently represent hydrogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxycarbonyl; R ⁶ and R ⁷ each represent hydrogen; R ⁸ and R ⁹ are each Independently from each other, hydrogen, halogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₃ - C ₄ alkenyloxy, C ₃ -C ₄ alkynyloxy, C ₁ -C ₄ alkoxycarbonyl, C ₃ -C ₆ cycloalkyl, CONH ₂ , CONH(C ₁ -C ₄ alkyl), CON( C ₁ -C ₄ alkyl) ₂ , NH ₂ , NHCO (C ₁ -C ₄ alkyl), NHCO (C ₂ -C ₄ alkenyl), NHCO (C ₂ -C ₄ alkynyl), NHCO phenyl, CHN-OH, phenyl or a 5-membered heterocyclic ring containing two or four heteroatoms independently selected from O and N (provided that the heterocyclic ring does not contain contiguous oxygen atoms), wherein the alkyl group can be Optionally, one or more are independently selected from the group consisting of halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, benzyloxy, NH ₂ , NHCO (C ₁ -C ₄ alkyl), NHCO (C ₂ -C ₄ alkenyl), NHCO (C ₂ -C ₄ alkynyl ), NHCO phenyl and substituted phenyl groups and wherein the heterocyclic ring is substituted by one or more C ₁ -C ₄ alkyl.

R ¹² and R ^{12 '} each independently represent hydrogen or C ₁ -C ₄ alkyl; R ¹³ and R ^{13 '} each independently represent hydrogen or C ₁ -C ₄ alkyl.

In another group of compounds, D ¹ , D ² , D ³ and D ⁴ each represent hydrogen; D ⁵ and D ⁶ independently of each other represent hydrogen, C ₁ -C ₄ alkyl, phenyl, including one to three independently a 5-membered heterocyclic ring selected from the heteroatoms of 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 phenyl group and the hetero atom The ring may be optionally substituted with one or more groups independently selected from the group consisting of halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl, and C ₁ -C ₄ haloalkyl.

X is X-3 or X-5; Z ³ , Z ⁵ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ independently of each other represent CR ⁴ R ⁵ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ or C=OR ⁶ R ⁷ ; Q is selected from the group consisting of Q-1, Q2, Q-3, and Q-9; Q' is selected from the group consisting of: Q -1', Q2', Q-3' and Q-9'; Y ¹ , Y ² , Y ³ , Y ^{1 '} , Y ^{2 '} and Y ^{3 '} each independently represent hydrogen or C ₁ -C ₄ alkane Each of Y ⁴ and Y ^{4 '} independently of one another represents hydrogen, halogen, OH, C ₁ -C ₄ alkyl, phenyl, wherein the phenyl group may be optionally substituted with one or more groups, for example, one to Five groups, independently selected from C ₁ -C ₄ alkyl; when Q' is Q-2', Y ^{2 '} and Y ^{3 '} together with the ring segments to which they are attached may form part or not at all A saturated 6-membered carbocyclic ring wherein the ring formed by Y ^{2 '} and Y ^{3 '} can be optionally substituted with one or more groups independently selected from C ₁ -C ₄ alkyl.

When Q is Q-3, Y ¹ and D ¹ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring; when Q' is Q-3', Y ^{1 '} and D ⁴ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring; when Q is Q-9 and L ¹ is CD ¹ , then R ¹² and D ¹ may together be - ( G ¹ ) _p -G ² -G ³ -; when Q' is Q-9' and L ⁴ is CD ⁴ , then R ^12' together with D ⁴ may be -(G ¹ ) _p -G ² -G ³ - G ¹ , G ² and G ³ represent a methylene group; p represents 1; R ⁴ and R ⁵ each independently represent hydrogen or a C ₁ -C ₂ alkoxycarbonyl group; and R ⁶ and R ⁷ each represent a hydrogen; R ⁸ and R ⁹ each independently represent hydrogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₁ -C ₄ alkoxy, C ₃ -C ₄ olefin a C ₁ -C ₄ alkoxycarbonyl group, CONH ₂ , CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl group is optionally independently selected from OH via one or more Substituting a C ₁ -C ₄ alkoxy group, a benzyloxy group, a NH ₂ , an NHCO phenyl group, and a phenyl group and wherein the tetrazolyl group is optionally substituted with a C ₁ -C ₄ alkyl group; R ¹² and R ^{12 'are} each independently from each other Represents a C ₁ -C ₄ alkyl; R ¹³ and R ^{13 'each} independently of one another represent C ₁ -C ₄ alkyl.

In another group of compounds, D ¹ , D ² , D ³ and D ⁴ each represent hydrogen; D ⁵ and D ⁶ independently of each other represent hydrogen, C ₁ -C ₄ alkyl, phenyl, including one to three independently a 5-membered heterocyclic ring selected from the heteroatoms of 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 phenyl group and the hetero atom The ring may be optionally substituted with one or more groups independently selected from the group consisting of halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl, and C ₁ -C ₄ haloalkyl.

X series X-3 or X-5; Z ³ , Z ⁵ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ independently of each other represent CR ⁴ R ⁵ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ or C=CR ⁶ R ⁷ ; Q is selected from the group consisting of Q-1, Q2, Q-3, and Q-9; Q' is selected from the group consisting of: Q -1', Q2', Q-3', and Q-9'; Y ¹ , Y ² , Y ³ , Y ^{1 '} , Y ^2', and Y ^3' independently of each other represent hydrogen or C ₁ -C ₄ alkyl ; Y ⁴ and Y ^{4 '} each independently represent hydrogen, OH, C ₁ -C ₄ alkyl or phenyl, wherein the phenyl group may be optionally substituted with one or more groups, for example one to five groups , independently selected from C ₁ -C ₄ alkyl; when Q is Q-2, Y ² and Y ³ together with the ring segments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring, Wherein the ring formed by Y ² and Y ³ may be optionally substituted with one or more groups independently selected from C ₁ -C ₄ alkyl; when Q' is Q-2', Y ^2' and Y ^3' together with the ring segments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by Y ^{2 '} and Y ^{3 '} may optionally be independently selected by one or more From C ₁ -C ₄ alkyl Replaced by the group.

When Q is Q-3, Y ¹ and D ¹ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring; when Q' is Q-3', Y ^1' and D ⁴ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring; when Q is Q-9 and L ¹ is CD ¹ , then R ¹² and D ¹ may together be -( G ¹ ) _p -G ² -G ³ -; when Q' is Q-9' and L ⁴ is CD ⁴ , then R ^12' together with D ⁴ may be -(G ¹ ) _p -G ² -G ³ -; G ¹ , G ² and G ³ represent a methylene group; p represents 1; R ⁴ , R ⁵ , R ⁶ and R ⁷ each represent hydrogen; and R ⁸ and R ⁹ each independently represent hydrogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₄ alkenyloxy, C ₁ -C ₄ alkoxycarbonyl, CHN-OH, or dioxolyl Wherein the alkyl group is optionally independently selected from OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, benzyloxy, by one or more And a group of a phenyl group; R ¹² and R ^{12 '} each independently represent a C ₁ -C ₄ alkyl group; and R ¹³ and R ^{13 '} each independently represent a C ₁ -C ₄ alkyl group.

In another group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other 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, C ₁ -C ₄ alkoxy, phenyl, containing one to three independently selected from O, S and N a 5- or 6-membered heterocyclic ring of a hetero atom (provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms, such as a heterocyclic ring as defined herein, preferably Is furanyl, thiophenyl or pyrazolyl), COR ¹ , OR ² , SH, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfinyl, C ₁ -C ₈ alkyl Sulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, N(R ³ ) ₂ , CO ₂ R ² , O(CO)R ¹ , CON(R ³ ) ₂ , NR ³ COR ¹ or CR ¹ N-OR ² wherein the alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, phenyl and heterocyclic ring may be optionally substituted by one or more groups, for example one to five a group, independently selected from the group consisting of halogen, CN, NH ₂ , NO ₂ , OR ² , C ₁ -C ₄ alkyl, and C ₁ -C ₄ haloalkyl; X represents X-3, X-4 or X-5; Z ^{3 Z 5, Z 6, Z 7} , Z 8, Z 9, Z 10, Z 11, Z 13 and Z ¹⁴ each independently represent CR ⁴ R ⁵ or ^{C = CR 6 R 7; Z} 4 and Z ¹² denotes CR ⁸ R ⁹ , SiR ¹⁰ R ¹¹ , C=O or C=CR ⁶ R ⁷ ; Q is selected from the group consisting of Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and Q-9; Q' is selected from the group consisting of Q-1', Q-2', Q-3' , Q-4', Q-5', Q-6', Q-7', Q-8', and Q-9'; Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^3' and Y ^4' each independently represent hydrogen, halogen, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio or phenyl, wherein The phenyl group may be optionally substituted by one or more groups, for example one to five groups, independently selected from halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ alkoxy group and C ₁ -C ₄ haloalkoxy group; when Q system Q-1, Q-2, Q-3, Q-4, Q-6 or Q-7, Y ¹ and Y ² , Y ² and Y ^3, or Y ³ and Y ⁴ are independently attached to a ring together with their fragments each other which may be formed partially or fully unsaturated 5- to 7-membered carbocyclic ring containing one to three or independently selected from N, and 5- to 7-membered heterocyclic ring N (R ³⁾ hetero atoms, and wherein the Y ¹ and Y ^2, Y ² and Y ^3, or Y ³ and Y ⁴ may form a ring optionally substituted with one Or a plurality of independently 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, C ₁ -C ₄ haloalkane a group substituted with an oxy group and a C ₁ -C ₄ alkylthio group; when Q' is a Q-1', Q-2', Q-3', Q-4', Q-6' or Q-7' , Y ^{1 '} and Y ^{2 '} , Y ^{2 '} and Y ^{3 '} , or Y ^{3 '} and Y ^{4 '} independently of each other together with the ring segment to which they are attached may form a partially or fully unsaturated 5- to 7 a meta carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R ³ ), and wherein Y ^{1 '} and Y ^{2 '} , Y ^{2 '} and Y ³ The ring formed by ^' , or Y ^{3 '} and Y ^{4 '} may optionally be selected from one or more independently selected from the group consisting of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C Substitution of a _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.

When Q is Q-1, Q-3, Q-4, Q-7 or Q-8 and L ¹ is CD ¹ , then Y ¹ and D ¹ together with the fragments to which they are attached may form part or all An unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by D ¹ and Y ¹ may be optionally substituted with one or more groups, for example one to five groups, independently selected from halo, CN, 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; when Q system Q- When 1', Q-3', Q-4', Q-7' or Q-8' and L ⁴ is CD ⁴ , then Y ¹ 'and D ⁴ together with the fragments to which they are attached may form part or a fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by D ¹ and Y ¹ may be optionally substituted with one or more groups, for example one to five groups, independently selected from halo, CN , 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; when Q system Q -9 and L ¹ is CD ¹ , then R ¹² and D ¹ may together be -(G ¹ ) _p -G ² -G ³ -; when Q' is Q-9' and L ⁴ is CD ⁴ , then R ^{12 'and} D ⁴ may together are _{^{- (G 1) p -G 2}} -G 3 -; G 1, G 2 to G ³ represents C (R ²¹⁾ _2, wherein each R ²¹ independently represents hydrogen, halogen, C ₁ -C ₄ alkyl each other, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy groups or C ₁ -C ₄ haloalkoxy; each p independently of 1 or 2; each R ¹ independently of ^one another represents hydrogen, C ₁ -C ₄ alkyl or phenyl, wherein the alkyl and phenyl are optionally Substituted by one or more groups independently selected from the group consisting of halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, and C ₁ -C ₄ haloalkoxy; R ² independently of each other 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 halo An alkynyl, phenyl, benzyl or pyridyl group, wherein the phenyl, benzyl and pyridyl groups are optionally independently selected from halo, CN, NH ₂ , NO ₂ , OH, C ₁ - Substituted by a C ₄ alkyl group, a C ₁ -C ₄ -haloalkyl group, a C ₁ -C ₄ alkoxy group, and a C ₁ -C ₄ haloalkoxy group; each R ³ independently represents hydrogen or C ₁ -C ₄ alkyl; wherein when two R ³ groups attached to the same nitrogen atom, such groups may be the same or different; and which When two R ³ groups attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached to form a ring which may be B-1, B-2, B-3, B-4 , or B-5, wherein the ring formed may be optionally substituted by one or more groups, for example one to five groups, independently selected from halogen, methyl or halomethyl; R ⁴ and R ⁵ are each Independently represents hydrogen, halogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₃ -C _{a 4} -alkenyloxy group, a C ₁ -C ₄ alkoxycarbonyl group, a C ₃ -C ₆ cycloalkyl group, CON(R ³ ) ₂ , NH ₂ , NR ³ COR ¹ or CR ¹ N-OR ² , wherein the alkyl group An alkenyl group, an alkynyl group, optionally, one or more independently selected from the group consisting of halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, a C ₁ -C ₄ haloalkoxy group and a group of NH ₂ are substituted; R ⁶ and R ⁷ each independently represent hydrogen, halogen, methyl or halomethyl; and R ⁸ and R ⁹ each independently represent hydrogen and halogen. , CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₃ -C ₄ alkenyloxy, C _3- C ₄ alkyne a group, C ₁ -C ₄ alkoxycarbonyl, C ₃ -C ₆ cycloalkyl, CONH ₂ , CONH(C ₁ -C ₄ alkyl), CON(C ₁ -C ₄ alkyl) ₂ , NH ₂ , NHCO (C ₁ -C ₄ alkyl), NHCO (C ₂ -C ₄ alkenyl), NHCO (C ₂ -C ₄ alkynyl), NHCO phenyl, CHN-OH, phenyl or contains two or four a 5-membered heterocyclic ring independently selected from the heteroatoms of O and N (provided that the heterocyclic ring does not contain contiguous oxygen atoms), wherein the alkyl group is optionally independently selected from halo by one or more , OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, benzyloxy, NH ₂ , NHCO (C ₁ -C ₄ alkyl), NHCO ( Substituents of C ₂ -C ₄ alkenyl), NHCO (C ₂ -C ₄ alkynyl), NHCO phenyl and phenyl are substituted and wherein the heterocyclic ring is substituted by one or more C ₁ -C ₄ alkyl groups.

R ¹⁰ and R ¹¹ each independently represent hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or phenyl, wherein the phenyl may optionally be passed through one or more a group substituted, for example one to five groups, independently selected from the group consisting of halogen, CN, methyl, halomethyl, methoxy and halomethoxy; R ¹² and R ^12' independently of each other represent 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 ² O)carbonyl (C ₁ -C _4- alkyl), wherein the alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, and pyridyl groups are optionally substituted with one or more groups, for example one to five groups, independently selected from halo , CN, OR ² , 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 and pyridyl; R ¹³ and R ^{13 '} independently of each other represent C ₁ -C ₄ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl or benzyl, wherein the alkyl The alkenyl, alkynyl and benzyl groups may be optionally substituted by one or more groups, for example one to five groups, independently selected from halogen, CN, C ₁ - C ₄ alkoxy and C ₁ -C ₄ haloalkoxy; in another group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other represent hydrogen, CN, C ₁ - a C ₄ alkyl group, a C ₁ -C ₄ alkoxy group, a phenyl group or a 5-membered heterocyclic ring containing one to three hetero atoms independently selected from O, S and N (provided that the heterocyclic ring does not contain a contiguous Oxygen atom, contiguous sulfur atom or contiguous sulfur and oxygen atom), wherein the phenyl group and the heterocyclic ring are optionally independently selected from halogen, C ₁ -C ₄ alkoxy, C ₁ via one or more Substituted by a group of -C ₄ alkyl and C ₁ -C ₄ haloalkyl; X represents X-3 or X-5; Z ³ , Z ⁵ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ independently represent CR ⁴ R ⁵ or C=CR ⁶ R ⁷ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ or C=CR ⁶ R ⁷ ; the Q system is selected from the group consisting of Q-1, Q- 2. Q-3 and Q-9; Q' is selected from the group consisting of Q-1', Q-2', Q-3' and Q-9'; Y ¹ , Y ² , Y ³ , Y ^{4 ,} , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently represent hydrogen, halogen, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy group, C ₁ -C ₄ alkylthio or phenyl, In the phenyl group may be optionally substituted with one or more groups independently selected from C ₁ -C ₄ alkyl group; each Y ² and Y ^3, together with the ring to which they are attached may form part of the fragment or a fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y ² and Y ³ is optionally independently selected from halo, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ via one or more a group substituted with a haloalkyl group, a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ haloalkoxy group, and a C ₁ -C ₄ alkylthio group; each group Y ^{2 '} and Y ^{3 '} together with them attached thereto Ring segments may form a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y ^{2 '} and Y ^{3 '} may be optionally independently selected from halo, CN, C ₁ -C via one or more _a group substituted with a ₄ alkyl group, 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; when the Q system is Q-1 or When Q-3 and L ¹ are CD ¹ , then Y ¹ and D ¹ together with the fragments to which they are attached may form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D ¹ and Y ¹ may be Optionally substituted with one or more groups, such as one or two groups, independently selected from the group consisting of halogen, CN, OH, methyl, Substituting methyl, methoxy and halomethoxy; when Q 'line Q-1' or Q-3 'and L ⁴ based upon CD ^4, the Y ^1' and D ⁴ on which they are attached to, together with the The fragment may form a fully unsaturated 6-membered carbocyclic ring wherein the ring formed by D ⁴ and Y ^{1 '} may be optionally substituted with one or more groups, such as one or two groups, independently selected from halo. , CN, OH, methyl, halomethyl, methoxy and halomethoxy; when Q is Q-9 and L ¹ is CD ¹ , then R ¹² and D ¹ can be together - (G ¹ _p -G ² -G ³ -; when Q' is Q-9' and L ⁴ is CD ⁴ , then R ^12' and D ⁴ may together be -(G ¹ ) _p -G ² -G ³ -; G ¹ , G ² and G ³ represent C(R ²¹ ) ₂ ; each R ²¹ independently of one another represents hydrogen or C ₁ -C ₄ alkyl; each p independently of one another represents 1 or 2; R ⁴ and R ⁵ Each independently represents hydrogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxycarbonyl; R ⁶ and R ⁷ each represent hydrogen; R ⁸ and R ⁹ each independently represent hydrogen, halogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₃ -C ₄ alkenyloxy, C ₃ -C ₄ alkynyloxy, C ₁ -C ₄ alkoxycarbonyl, C ₃ -C ₆ cycloalkyl, CONH ₂ , CONH (C ₁ -C ₄ alkyl), CON(C ₁ -C ₄ alkyl) ₂ , NH ₂ , NHCO (C ₁ -C ₄ alkyl), NHCO (C _2- C ₄ alkenyl), NHCO (C ₂ -C ₄ alkynyl), NHCO phenyl, CHN-OH, phenyl or 5-member containing two or four heteroatoms independently selected from O and N heterocyclic ring (with the proviso lines: the heterocyclic ring does not contain adjacent oxygen atoms) wherein the alkyl group may be optionally substituted with one or more groups independently selected from _{halogen, OH, CN, C 1 -C} 4 alkyl, C _1- C ₄ haloalkyl, C ₁ -C ₄ alkoxy, benzyloxy, NH ₂ , NHCO (C ₁ -C ₄ alkyl), NHCO (C ₂ -C ₄ alkenyl), NHCO (C ₂ - Substituted with a C ₄ alkynyl group, an NHCO phenyl group, and a phenyl group, and wherein the heterocyclic ring is substituted with one or more C ₁ -C ₄ alkyl groups; R ¹² and R ^{12 '} each independently represent hydrogen or C ₁ -C ₄ alkyl; R ¹³ and R ^13' independently of each other represent hydrogen, C ₁ -C ₄ alkyl or C ₃ -C ₆ alkynyl.

In another group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of one another represent hydrogen, C ₁ -C ₄ alkyl, phenyl or comprise one to three independently selected from O. a 5-membered heterocyclic ring of a hetero atom of 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 phenyl group and the heterocyclic ring are optional Optionally substituted with one or more groups independently selected from the group consisting of halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl, and C ₁ -C ₄ haloalkyl; X-ray X-3 or X- 5; Z ³ , Z ⁵ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ independently of each other represent CR ⁴ R ⁵ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ or C=CR ⁶ R ⁷ ; Q is selected from The lower group consists of the following: Q-1, Q-2, Q-3, and Q-9; the Q' is selected from the group consisting of the following: Q-1', Q- 2', Q-3' and Q-9'; Y ¹ , Y ² , Y ³ , Y ^{1 '} , Y ^{2 '} and Y ^{3 '} each independently represent hydrogen or C ₁ -C ₄ alkyl; Y ⁴ And Y ^4' each independently represent hydrogen, halogen, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio or phenyl, wherein the phenyl is capable Choose one or one Groups substituted by, for example one to five groups independently selected from C ₁ -C ₄ alkyl; and when Q when Q-2 system, Y ² and Y ^3, together with the ring to which they are attached may form part of the fragment Or a fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y ^{2 '} and Y ^{3 '} can be optionally substituted with one or more groups independently selected from C ₁ -C ₄ alkyl; When 'Q-2', Y ^{2 '} and Y ^{3 '} together with the ring segments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring, wherein Y ^{2 '} and Y ^{3 ' are} formed. The ring may be optionally substituted with one or more groups independently selected from C ₁ -C ₄ alkyl.

When Q is Q-3, Y ¹ and D ¹ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring; when Q' is Q-3', Y ^1' and D ⁴ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring; when Q is Q-9 and L ¹ is CD ¹ , then R ¹² and D ¹ may together be -( _{^{G 1) p -G 2 -G 3}} -; when Q 'line Q-9' and the line L ⁴ CD ^4, the R ^{12 'and} D ⁴ may together are _{^{- (G 1) p -G 2}} -G 3 - G ¹ , G ² and G ³ represent a methylene group; p represents 1; R ⁴ and R ⁵ each independently represent hydrogen or a C ₁ -C ₂ alkoxycarbonyl group; and R ⁶ and R ⁷ each represent a hydrogen; R ⁸ and R ⁹ each independently represent hydrogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₁ -C ₄ alkoxy, C ₃ -C ₄ olefin a C ₁ -C ₄ alkoxycarbonyl group, CONH ₂ , CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl group is optionally independently selected from OH via one or more Substituting a C ₁ -C ₄ alkoxy group, a benzyloxy group, a NH ₂ , an NHCO phenyl group, and a phenyl group and wherein the tetrazolyl group is optionally substituted with a C ₁ -C ₄ alkyl group; R ¹² and R ^{12 'are} each independently from each other Represents a C ₁ -C ₄ alkyl; R ¹³ and R ^{13 'independently} of one another represent hydrogen, C ₁ -C ₄ alkyl or C ₃ -C ₆ alkynyl group.

In another group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of one another represent hydrogen, C ₁ -C ₄ alkyl, phenyl or comprise one to three independently selected from O. a 5-membered heterocyclic ring of a hetero atom of 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 phenyl group and the heterocyclic ring are optional Optionally substituted with one or more groups independently selected from the group consisting of halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl, and C ₁ -C ₄ haloalkyl; X-ray X-3 or X- 5; Z ³ , Z ⁵ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ independently of each other represent CR ⁴ R ⁵ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ or C=CR ⁶ R ⁷ ; Q is selected from The lower group consists of the following: Q-1, Q2, Q-3, and Q-9; the Q' is selected from the group consisting of the following: Q-1', Q2', Q -3' and Q-9'; Y ¹ , Y ² , Y ³ , Y ^{1 '} , Y ^{2 '} and Y ^{3 '} independently of each other represent hydrogen or C ₁ -C ₄ alkyl; Y ⁴ and Y ^4' are each Independently from each other, represents hydrogen, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio or phenyl, wherein the phenyl group may optionally be subjected to one or more Group substitution For example, one to five groups independently selected from C ₁ -C ₄ alkyl; and when Q based ^Q-2, Y 2 and Y ³ together with their attached to the ring segment which may form part or fully unsaturated a 6-membered carbocyclic ring wherein the ring formed by Y ² and Y ³ may be optionally substituted with one or more groups independently selected from C ₁ -C ₄ alkyl; when Q' is Q-2' , Y ^{2 '} and Y ^{3 '} together with the ring segments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by Y ^{2 '} and Y ^{3 '} may optionally be passed through a ring Or a plurality of groups independently selected from C ₁ -C ₄ alkyl groups.

When Q is Q-3, Y ¹ and D ¹ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring; when Q' is Q-3', Y ^1' and D ⁴ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring; when Q is Q-9 and L ¹ is CD ¹ , then R ¹² and D ¹ may together be -( G ¹ ) _p -G ² -G ³ -; when Q' is Q-9' and L ⁴ is CD ⁴ , then R ^12' together with D ⁴ may be -(G ¹ ) _p -G ² -G ³ -; G ¹ , G ² and G ³ represent a methylene group; p represents 1; R ⁴ , R ⁵ , R ⁶ and R ⁷ each represent hydrogen; and R ⁸ and R ⁹ each independently represent hydrogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₄ alkenyloxy, C ₁ -C ₄ alkoxycarbonyl, CHN-OH, tetrazolyl or diox heterocycle Pentenyl, wherein the alkyl group is optionally independently selected from OH, CN, NH ₂ , NHCO phenyl, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ a group substituted with a -C ₄ alkoxy group, a benzyloxy group, and a phenyl group, and wherein the tetrazolyl group is optionally substituted with a C ₁ -C ₄ alkyl group; R ¹² and R ^{12 '} each independently represent C ₁ -C ₄ alkyl; R ¹³ to R ^{13 'independently} of one another represent hydrogen, C ₁ -C ₄ alkyl or C ₃ -C ₆ alkynyl group.

In another group of compounds, D ¹ , D ² , D ³ and D ⁴ independently of each other represent hydrogen, C ₁ -C ₄ alkyl, CN or C ₁ -C ₄ alkoxy, wherein the alkyl and alkoxy The group may be optionally substituted by one or more groups, for example one to five groups, independently selected from the group consisting of halogen, CN, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy; D ⁵ and D ⁶ independently of each other represents 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 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 contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and An oxygen atom, for example a heterocyclic ring as defined herein, preferably a furyl, thiophenyl or pyrazolyl), COR ¹ , OR ² , SH, a C ₁ -C ₈ alkylthio group, a C ₁ -C ₈ Alkylsulfinyl, C ₁ -C ₈ alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, N(R ³ ) ₂ , CO ₂ R ² , O (CO ^{) R 1, CON (R 3} ) 2, NR 3 COR 1 or CR ¹ N-oR ^2, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and heterocycle may be Optionally substituted with one or more groups, for example one to five groups independently selected from _{halogen, CN, NH 2, NO 2} , OR 2, C 1 -C 4 alkyl and C ₁ -C ₄ haloalkyl, X represents X-3, X-4 or X-5; Z ³ , Z ⁵ , Z ⁶ , Z ⁷ , Z ⁸ , Z ⁹ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ independently represent CR ⁴ R ⁵ or C=CR ⁶ R ⁷ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ , SiR ¹⁰ R ¹¹ , C=O or C=CR ⁶ R ⁷ ; the Q system is selected from the group consisting of the following Composition: Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and Q-9; Q' is selected from the group consisting of the following Composition: Q-1', Q-2', Q-3', Q-4', Q-5', Q-6', Q-7', Q-8' and Q-9'; Y ¹ , Y ² , Y ³ , Y ^{4 ,} , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently represent hydrogen, halogen, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio or phenyl, where the phenyl is optionally substituted with one or more groups, for example 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; when Q system Q-1, Q-2, Q-3, Q -4, Q-6 When Q-7, Y ¹ and Y ^2, Y ² and Y ^3, or Y ³ and Y ⁴ are independently attached to a ring together with their fragments which may be formed partially or fully unsaturated 5- to 7-membered one another a carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R ³ ), and wherein Y ¹ and Y ² , Y ² and Y ³ , or Y ³ and The ring formed by Y ⁴ may be optionally selected from one or more independently 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, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ alkylthio groups; when Q 'line Q-1', Q-2 ', Q-3', Q-4 ' , Q-6' or Q-7', Y ^{1 '} and Y ^{2 '} , Y ^{2 '} and Y ^{3 '} , or Y ^{3 '} and Y ^{4 '} independently of each other together with the ring fragment to which they are attached may Forming a partially or fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R ³ ), and wherein Y ^{1 '} Rings formed with Y ^{2 '} , Y ^{2 '} and Y ^{3 '} , or Y ^{3 '} and Y ^{4 '} may be optionally independently selected from halogen, CN, NH ₂ , NO ₂ , OH, C via one or more ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy Group, a substituted C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ alkylthio groups.

When Q is Q-1, Q-3, Q-4, Q-7 or Q-8 and L ¹ is CD ¹ , then Y ¹ and D ¹ together with the fragments to which they are attached may form part or all An unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by D ¹ and Y ¹ may be optionally substituted with one or more groups, for example one to five groups, independently selected from halo, CN, 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; when Q system Q- When 1', Q-3', Q-4', Q-7' or Q-8' and L ⁴ is CD ⁴ , then Y ¹ 'and D ⁴ together with the fragments to which they are attached may form part or a fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by D ¹ and Y ¹ may be optionally substituted with one or more groups, for example one to five groups, independently selected from halo, CN , 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; when Q system Q -9 and L ¹ is CD ¹ , then R ¹² and D ¹ may together be -(G ¹ ) _p -G ² -G ³ -; when Q' is Q-9' and L ⁴ is CD ⁴ , then R ^{12 'and} D ⁴ may together are _{^{- (G 1) p -G 2}} -G 3 -; G 1, G 2 to G ³ represents C (R ²¹⁾ _2, wherein each R ²¹ independently represents hydrogen, halogen, C ₁ -C ₄ alkyl each other, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy groups or C ₁ -C ₄ haloalkoxy; each p independently of 1 or 2; each R ¹ independently of ^one another represents hydrogen, C ₁ -C ₄ alkyl or phenyl, wherein the alkyl and phenyl are optionally Substituted by one or more groups independently selected from the group consisting of halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, and C ₁ -C ₄ haloalkoxy; R ² independently of each other 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 halo An alkynyl, phenyl, benzyl or pyridyl group, wherein the phenyl, benzyl and pyridyl groups are optionally independently selected from halo, CN, NH ₂ , NO ₂ , OH, C ₁ - Substituted by a C ₄ alkyl group, a C ₁ -C ₄ -haloalkyl group, a C ₁ -C ₄ alkoxy group, and a C ₁ -C ₄ haloalkoxy group; each R ³ independently represents hydrogen or C ₁ -C ₄ alkyl; wherein when two R ³ groups attached to the same nitrogen atom, such groups may be the same or different; and which When two R ³ groups attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached to form a ring which may be B-1, B-2, B-3, B-4 , or B-5, wherein the ring formed may be optionally substituted by one or more groups, for example one to five groups, independently selected from halogen, methyl or halomethyl; R ⁴ and R ⁵ are each Independently represents hydrogen, halogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₃ -C _{a 4} -alkenyloxy group, a C ₁ -C ₄ alkoxycarbonyl group, a C ₃ -C ₆ cycloalkyl group, CON(R ³ ) ₂ , NH ₂ , NR ³ COR ¹ or CR ¹ N-OR ² , wherein the alkyl group An alkenyl group, an alkynyl group, optionally, one or more independently selected from the group consisting of halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, a C ₁ -C ₄ haloalkoxy group and a group of NH ₂ are substituted; R ⁶ and R ⁷ each independently represent hydrogen, halogen, methyl or halomethyl; and R ⁸ and R ⁹ each independently represent hydrogen and halogen. , CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₃ -C ₄ alkenyloxy, C _3- C ₄ alkyne a group, C ₁ -C ₄ alkoxycarbonyl, C ₃ -C ₆ cycloalkyl, CONH ₂ , CONH(C ₁ -C ₄ alkyl), CON(C ₁ -C ₄ alkyl) ₂ , NH ₂ , NHCO (C ₁ -C ₄ alkyl), NHCO (C ₂ -C ₄ alkenyl), NHCO (C ₂ -C ₄ alkynyl), NHCO phenyl, CHN-OH, phenyl or contains two or four a 5-membered heterocyclic ring independently selected from the heteroatoms of O and N (provided that the heterocyclic ring does not contain contiguous oxygen atoms), wherein the alkyl group is optionally independently selected from halo by one or more , OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, benzyloxy, NH ₂ , NHCO (C ₁ -C ₄ alkyl), NHCO ( Substituents of C ₂ -C ₄ alkenyl), NHCO (C ₂ -C ₄ alkynyl), NHCO phenyl and phenyl are substituted and wherein the heterocyclic ring is substituted by one or more C ₁ -C ₄ alkyl groups.

R ¹⁰ and R ¹¹ each independently represent hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or phenyl, wherein the phenyl may optionally be passed through one or more a group substituted, for example one to five groups, independently selected from the group consisting of halogen, CN, methyl, halomethyl, methoxy and halomethoxy; R ¹² and R ^12' independently of each other represent 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 ² O)carbonyl (C ₁ -C _4- alkyl), wherein the alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, and pyridyl groups are optionally substituted with one or more groups, for example one to five groups, independently selected from halo , CN, OR ² , 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 and pyridyl; R ¹³ and R ^{13 '} independently of each other represent C ₁ -C ₄ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl or benzyl, wherein the alkyl The alkenyl, alkynyl and benzyl groups may be optionally substituted by one or more groups, for example one to five groups, independently selected from halogen, CN, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy.

In another group of compounds, D ¹ , D ² , D ³ and D ⁴ independently of each other represent hydrogen, C ₁ -C ₄ alkyl, CN or C ₁ -C ₄ alkoxy; D ⁵ and D ⁶ are independent of each other Ground represents hydrogen, C ₁ -C ₄ alkyl, phenyl, 5-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S and N (provided that the heterocyclic ring does not contain contiguous oxygen An atom, an adjacent sulfur atom or an adjacent sulfur and oxygen atom), wherein the phenyl group and the heterocyclic ring are optionally independently selected from halogen, C ₁ -C ₄ alkoxy, C ₁ -C via one or more _The group of ₄ alkyl and C ₁ -C ₄ haloalkyl is substituted.

X represents X-3 or X-5; Z ³ , Z ⁵ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ independently of each other represent CR ⁴ R ⁵ or C=CR ⁶ R ⁷ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ or C=CR ⁶ R ⁷ ; the Q system is selected from the group consisting of Q-1, Q-2, Q-3 and Q-9; the Q' is selected from the group consisting of This group consists of: Q-1', Q-2', Q-3', and Q-9'; Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^3' and Y ^4' each independently represent hydrogen, halogen, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio or phenyl, wherein the phenyl Optionally substituted with one or more groups independently selected from C ₁ -C ₄ alkyl; each group of Y ² and Y ³ together with the ring segments to which they are attached may form partially or fully unsaturated a 6-membered carbocyclic ring wherein the ring formed by Y ² and Y ³ is optionally independently selected from halo, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C _a group substituted with ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ alkylthio; each group of Y ^{2 '} and Y ^{3 '} together with the ring segments to which they are attached may Forming a partially or fully unsaturated 6-membered carbon ring, wherein The ring formed by Y ^{2 '} and Y ^{3 '} can be optionally selected from one or more independently selected from the group consisting of halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkane. a group substituted with an oxy group, a C ₁ -C ₄ haloalkoxy group, and a C ₁ -C ₄ alkylthio group; when the Q system is Q-1 or Q-3 and the L ¹ is CD ¹ , then Y ¹ and D ¹ together The fragments to which they are attached may form a fully unsaturated 6-membered carbocyclic ring wherein the ring formed by D ¹ and Y ¹ may be optionally substituted with one or more groups, for example one or two groups , independently selected from the group consisting of halogen, CN, OH, methyl, halomethyl, methoxy, and halomethoxy; when Q' is Q-1' or Q-3' and L ⁴ is CD ⁴ Then Y ^{1 '} and D ⁴ together with the fragments to which they are attached may form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D ⁴ and Y ^{1 '} may optionally be subjected to one or more groups Substituted, for example, one or two groups, independently selected from the group consisting of halogen, CN, OH, methyl, halomethyl, methoxy, and halomethoxy; when Q is Q-9 and L ¹ is CD ¹ When R ¹² and D ¹ may together be -(G ¹ ) _p -G ² -G ³ -; when Q' is Q-9' and L ⁴ is CD ⁴ , then R ^12' and D ⁴ may be together Yes-( G ¹ ) _p -G ² -G ³ -; G ¹ , G ² and G ³ represent C(R ²¹ ) ₂ ; each R ²¹ independently of one another represents hydrogen or C ₁ -C ₄ alkyl; each p is mutually Independently represents 1 or 2; R ⁴ and R ⁵ each independently represent hydrogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxycarbonyl; R ⁶ and R ⁷ each represent hydrogen; R ⁸ and R ⁹ each independently represents hydrogen, halogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C _3- C ₄ alkenyloxy, C ₃ -C ₄ alkynyloxy, C ₁ -C ₄ alkoxycarbonyl, C ₃ -C ₆ cycloalkyl, CONH ₂ , CONH(C ₁ -C ₄ alkyl), CON(C ₁ -C ₄ alkyl) ₂ , NH ₂ , NHCO (C ₁ -C ₄ alkyl), NHCO (C ₂ -C ₄ alkenyl), NHCO (C ₂ -C ₄ alkynyl), NHCO benzene a group, CHN-OH, phenyl or a 5-membered heterocyclic ring containing two or four heteroatoms independently selected from O and N (provided that the heterocyclic ring does not contain contiguous oxygen atoms), wherein the alkane The group may optionally be selected from one or more independently selected from the group consisting of halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, benzyloxy, NH ₂ , NHCO (C ₁ -C ₄ alkyl), NHCO (C ₂ -C ₄ alkenyl), NHCO (C ₂ -C ₄ Alkynyl), NHCO phenyl, and phenyl groups are substituted, and wherein the heterocyclic ring is substituted with one or more C ₁ -C ₄ alkyl groups; R ¹² and R ^{12 '} each independently represent hydrogen or C ₁ -C ₄ alkyl; R ¹³ and R ^13' independently of each other represent hydrogen, C ₁ -C ₄ alkyl or C ₃ -C ₆ alkynyl.

In another group of compounds, D ¹ , D ² , D ³ and D ⁴ each represent hydrogen; D ⁵ and D ⁶ independently of each other represent hydrogen, C ₁ -C ₄ alkyl, phenyl or contain one to three independently a 5-membered heterocyclic ring selected from the heteroatoms of 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 phenyl group and the hetero atom The ring may be optionally substituted with one or more groups independently selected from the group consisting of halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl, and C ₁ -C ₄ haloalkyl; X-ray X-3 Or X-5; Z ³ , Z ⁵ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ independently of each other represent CR ⁴ R ⁵ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ or C=CR ⁶ R ⁷ ; The group is selected from the group consisting of Q-1, Q-2, Q-3, and Q-9; the Q' is selected from the group consisting of the following: Q-1' , Q-2', Q-3', and Q-9'; Y ¹ , Y ² , Y ³ , Y ^{1 '} , Y ^{2 ',} and Y ^{3 '} each independently represent hydrogen or C ₁ -C ₄ alkyl ; Y ⁴ and Y ^{4 '} each independently represent hydrogen, halogen, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio or phenyl, wherein the benzene Ke Keren Substituted with one or more substituent groups, for example one to five groups independently selected from C ₁ -C ₄ alkyl; and when Q based ^Q-2, Y 2 and Y ^3, together with which they are attached to the The ring segment may form a partially or fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by Y ^{2 '} and Y ^{3 '} may optionally be through one or more groups independently selected from C ₁ -C ₄ alkyl a group substitution; when Q' is Q-2', Y ^{2 '} and Y ^{3 '} together with the ring segment to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring, wherein Y ^{2 '} and The ring formed by Y ^{3 '} may be optionally substituted with one or more groups independently selected from C ₁ -C ₄ alkyl.

When Q is Q-3, Y ¹ and D ¹ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring; when Q' is Q-3', Y ^1' and D ⁴ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring; when Q is Q-9 and L ¹ is CD ¹ , then R ¹² and D ¹ may together be -( G ¹ ) _p -G ² -G ³ -; when Q' is Q-9' and L ⁴ is CD ⁴ , then R ^12' together with D ⁴ may be -(G ¹ ) _p -G ² -G ³ - G ¹ , G ² and G ³ represent a methylene group; p represents 1; R ⁴ and R ⁵ each independently represent hydrogen or a C ₁ -C ₂ alkoxycarbonyl group; R ⁶ and R ⁷ each represent a hydrogen; R ⁸ and R ⁹ each independently represent hydrogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₁ -C ₄ alkoxy, C ₃ -C ₄ olefin a C ₁ -C ₄ alkoxycarbonyl group, CONH ₂ , CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl group is optionally independently selected from OH via one or more Substituting a C ₁ -C ₄ alkoxy group, a benzyloxy group, a NH ₂ , an NHCO phenyl group, and a phenyl group and wherein the tetrazolyl group is optionally substituted with a C ₁ -C ₄ alkyl group; R ¹² and R ^{12 'are} each independently from each other Represents a C ₁ -C ₄ alkyl; R ¹³ and R ^{13 'independently} of one another represent hydrogen, C ₁ -C ₄ alkyl or C ₃ -C ₆ alkynyl group.

In another group of compounds, D ¹ , D ² , D ³ and D ⁴ each represent hydrogen; D ⁵ and D ⁶ independently of each other represent hydrogen, C ₁ -C ₄ alkyl, phenyl, including one to three independently a 5-membered heterocyclic ring selected from the heteroatoms of 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 phenyl group and the hetero atom The ring may be optionally substituted with one or more groups independently selected from the group consisting of halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl, and C ₁ -C ₄ haloalkyl.

X series X-3 or X-5; Z ³ , Z ⁵ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ independently of each other represent CR ⁴ R ⁵ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ or C=CR ⁶ R ⁷ ; Q is selected from the group consisting of Q-1, Q2, Q-3, and Q-9; Q' is selected from the group consisting of: Q -1', Q2', Q-3', and Q-9'; Y ¹ , Y ² , Y ³ , Y ^{1 '} , Y ^2', and Y ^3' independently of each other represent hydrogen or C ₁ -C ₄ alkyl And Y ⁴ and Y ^{4 '} each independently represent hydrogen, OH, C ₁ -C ₄ alkyl or phenyl, wherein the phenyl group may be optionally substituted by one or more groups, for example one to five groups , independently selected from C ₁ -C ₄ alkyl; when Q is Q-2, Y ² and Y ³ together with the ring segment to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring, Wherein the ring formed by Y ² and Y ³ may be optionally substituted with one or more groups independently selected from C ₁ -C ₄ alkyl; when Q' is Q-2', Y ^2' and Y ^3' together with the ring segments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by Y ^{2 '} and Y ^{3 '} may optionally be independently selected by one or more From C ₁ -C ₄ alkyl Replaced by the group.

When Q is Q-3, Y ¹ and D ¹ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring; when Q' is Q-3', Y ^1' and D ⁴ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring; when Q is Q-9 and L ¹ is CD ¹ , then R ¹² and D ¹ may together be -( G ¹ ) _p -G ² -G ³ -; when Q' is Q-9' and L ⁴ is CD ⁴ , then R ^12' together with D ⁴ may be -(G ¹ ) _p -G ² -G ³ -; G ¹ , G ² and G ³ represent a methylene group; p represents 1; R ⁴ , R ⁵ , R ⁶ and R ⁷ each represent hydrogen; and R ⁸ and R ⁹ each independently represent hydrogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₄ alkenyloxy, C ₁ -C ₄ alkoxycarbonyl, CHN-OH, tetrazolyl or diox heterocycle Pentenyl, wherein the alkyl group is optionally independently selected from OH, CN, NH _2, NHCO phenyl, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ a group substituted with a -C ₄ alkoxy group, a benzyloxy group, and a phenyl group, and wherein the tetrazolyl group is optionally substituted with a C ₁ -C ₄ alkyl group; R ¹² and R ^{12 '} each independently represent C ₁ -C ₄ alkyl; R ¹³ to R ^{13 'independently} of one another represent hydrogen, C ₁ -C ₄ alkyl or C ₃ -C ₆ alkynyl group.

In another group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other 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, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, phenyl, containing one to three a 5- or 6-membered heterocyclic ring independently selected from the heteroatoms of O, S and N (provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms, for example The heterocyclic ring defined herein, preferably furylthiophenyl or pyrazolyl), COR ¹ , OR ² , SH, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfinyl , C ₁ -C ₈ alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, N(R ³ ) ₂ , CO ₂ R ² , O(CO)R ¹ , CON( R ³ ) ₂ , NR ³ COR ¹ or CR ¹ N-OR ² , wherein the alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, phenyl and heterocyclic ring may optionally be passed through one or more a group substituted, for example one to five groups, independently selected from the group consisting of halogen, CN, NH ₂ , NO ₂ , OR ² , C ₁ -C ₄ alkyl and C ₁ -C ₄ haloalkyl; X represents X-3, X -4 or X-5; Z ³ , Z ⁵ , Z ⁶ , Z ⁷ , Z ⁸ , Z ⁹ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ independently of each other represent CR ⁴ R ⁵ or C=CR ⁶ R ⁷ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ , SiR ¹⁰ R ¹¹ , C=O or C=CR ⁶ R ⁷ ; the Q system is selected from the group consisting of Q-1, Q- 2. Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and Q-9; Q' is selected from the group consisting of the following: Q-1' , Q-2', Q-3', Q-4', Q-5', Q-6', Q-7', Q-8', and Q-9'; Y ¹ , Y ² , Y ³ , Y ^{4 ,} , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently represent hydrogen, halogen, OH, C ₁ -C ₄ alkyl, C ₂ -C ₆ alkynyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio or phenyl, where the phenyl is optionally substituted with one or more groups, for example 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; when Q system Q-1, Q-2, Q-3, Q -4, Q-6 or Q-7, Y ¹ and Y ² , Y ² and Y ³ , or Y ³ and Y ⁴ independently of each other together with the ring segment to which they are attached may form partial or complete unsaturation 5- to 7-membered carbon Or comprising one to three substituents independently selected from 5- to 7-membered heterocycle including the N and N (R ³⁾ hetero atoms, and wherein the Y ¹ and Y ^2, Y ² and Y ^3, or Y ³ and Y ⁴ The ring formed may optionally be selected from one or more independently 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 alkane a group substituted with an oxy group, a C ₁ -C ₄ haloalkoxy group, and a C ₁ -C ₄ alkylthio group; when Q' is a Q-1', Q-2', Q-3', Q-4', Q -6' or Q-7', Y ^{1 '} and Y ^{2 '} , Y ^{2 '} and Y ^{3 '} , or Y ^{3 '} and Y ^{4 '} independently of each other together with the ring fragment to which they are attached may form part Or a fully unsaturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R ³ ), and wherein Y ^{1 '} and Y The ring formed by ^2' , Y ^{2 '} and Y ^{3 '} ', or Y ^{3 '} and Y ^{4 '} may optionally be selected from one or more independently selected from the group consisting of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ Substituent substitution of -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ alkylthio.

When Q is Q-1, Q-3, Q-4, Q-7 or Q-8 and L ¹ is CD ¹ , then Y ¹ and D ¹ together with the fragments to which they are attached may form part or all An unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by D ¹ and Y ¹ may be optionally substituted with one or more groups, for example one to five groups, independently selected from halo, CN, 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; when Q system Q- When 1', Q-3', Q-4', Q-7' or Q-8' and L ⁴ is CD ⁴ , then Y ¹ 'and D ⁴ together with the fragments to which they are attached may form part or a fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by D ¹ and Y ¹ may be optionally substituted with one or more groups, for example one to five groups, independently selected from halo, CN , 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; when Q system Q -9 and L ¹ is CD ¹ , then R ¹² and D ¹ may together be -(G ¹ ) _p -G ² -G ³ -; when Q' is Q-9' and L ⁴ is CD ⁴ , then R ^{12 'and} D ⁴ may together are _{^{- (G 1) p -G 2}} -G 3 -; G 1, G 2 to G ³ represents C (R ²¹⁾ _2, wherein each R ²¹ independently represents hydrogen, halogen, C ₁ -C ₄ alkyl each other, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy groups or C ₁ -C ₄ haloalkoxy; each p independently of 1 or 2; each R ¹ independently of ^one another represents hydrogen, C ₁ -C ₄ alkyl or phenyl, wherein the alkyl and phenyl are optionally Substituted by one or more groups independently selected from the group consisting of halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, and C ₁ -C ₄ haloalkoxy; R ² independently of each other 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 halo An alkynyl, phenyl, benzyl or pyridyl group, wherein the phenyl, benzyl and pyridyl groups are optionally independently selected from halo, CN, NH ₂ , NO ₂ , OH, C ₁ - Substituted by a C ₄ alkyl group, a C ₁ -C ₄ -haloalkyl group, a C ₁ -C ₄ alkoxy group, and a C ₁ -C ₄ haloalkoxy group; each R ³ independently represents hydrogen or C ₁ -C ₄ alkyl; wherein when two R ³ groups attached to the same nitrogen atom, such groups may be the same or different; and which When two R ³ groups attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached to form a ring which may be B-1, B-2, B-3, B-4 , or B-5, wherein the ring formed may be optionally substituted by one or more groups, for example one to five groups, independently selected from halogen, methyl or halomethyl; R ⁴ and R ⁵ are each Independently represents hydrogen, halogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₃ -C _{a 4} -alkenyloxy group, a C ₁ -C ₄ alkoxycarbonyl group, a C ₃ -C ₆ cycloalkyl group, CON(R ³ ) ₂ , NH ₂ , NR ³ COR ¹ or CR ¹ N-OR ² , wherein the alkyl group An alkenyl group, an alkynyl group, optionally, one or more independently selected from the group consisting of halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, a C ₁ -C ₄ haloalkoxy group and a group of NH ₂ are substituted; R ⁶ and R ⁷ each independently represent hydrogen, halogen, methyl or halomethyl; and R ⁸ and R ⁹ each independently represent hydrogen and halogen. , CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₃ -C ₄ alkenyloxy, C ₃ -C ₄ alkynyloxy , C ₁ -C ₄ alkoxycarbonyl, C ₃ -C _{6 cycloalkyl, CONH 2, CONH (C 1} -C 4 alkyl), CON (C ₁ -C ₄ alkyl) _2, NH _2, NHCO (C ₁ -C ₄ alkyl), NHCO (C ₂ -C ₄ alkenyl), NHCO (C ₂ -C ₄ alkynyl), NHCO phenyl, CHN-OH, phenyl or contains two or four independent a 5-membered heterocyclic ring selected from the heteroatoms of O and N (provided that the heterocyclic ring does not contain contiguous oxygen atoms), wherein the alkyl group may be optionally independently selected from halogen, by one or more OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, benzyloxy, NH ₂ , NHCO (C ₁ -C ₄ alkyl), NHCO (C Substituted with a group of _2- C ₄ alkenyl), NHCO (C ₂ -C ₄ alkynyl), NHCO phenyl and phenyl and wherein the heterocyclic ring is substituted by one or more C ₁ -C ₄ alkyl groups.

R ¹⁰ and R ¹¹ each independently represent hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or phenyl, wherein the phenyl may optionally be passed through one or more a group substituted, for example one to five groups, independently selected from the group consisting of halogen, CN, methyl, halomethyl, methoxy and halomethoxy; R ¹² and R ^{12 '} independently of each other represent 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 ² O)carbonyl (C ₁ -C _4- alkyl), wherein the alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, and pyridyl groups are optionally substituted with one or more groups, for example one to five groups, independently selected from halo , CN, OR ² , 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 and pyridyl; R ¹³ and R ^{13 '} independently of each other represent C ₁ -C ₄ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl or benzyl, wherein the alkyl The alkenyl, alkynyl and benzyl groups may be optionally substituted by one or more groups, for example one to five groups, independently selected from halogen, CN, C ₁ - C ₄ alkoxy and C ₁ -C ₄ haloalkoxy.

Preferably, in the group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other represent hydrogen, halogen, CN, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, or phenyl containing from one to three substituents independently selected from O, S and N heteroatoms 5-membered heterocyclic ring (with the proviso that Is: the heterocyclic ring does not comprise an adjacent oxygen atom, an adjacent sulfur atom or an adjacent sulfur and oxygen atom), wherein the phenyl group and the heterocyclic ring are optionally independently selected from halogen, C ₁ - Substituted by a C ₄ alkoxy group, a C ₁ -C ₄ alkyl group, and a C ₁ -C ₄ haloalkyl group; X represents X-3 or X-5; Z ³ , Z ⁵ , Z ¹⁰ , Z ¹¹ , Z ¹³ And Z ¹⁴ independently of each other represents CR ⁴ R ⁵ or C=CR ⁶ R ⁷ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ or C=CR ⁶ R ⁷ ; the Q system is selected from the group consisting of the following Composition: Q-1, Q-2, Q-3, and Q-9; Q' is selected from the group consisting of Q-1', Q-2', Q-3', and Q. -9′; Y ¹ , Y ² , Y ³ , Y ^{4 ,} , Y ^1′ , Y ^2′ , Y ^3′ and Y ^4′ each independently represent hydrogen, halogen, OH, C ₁ -C ₄ alkyl , C ₂ -C ₈ alkynyl group, C ₁ -C ₄ alkoxy C ₁ -C ₄ alkylthio or phenyl, where the phenyl is optionally substituted with one or more substituents independently selected from C ₁ -C ₄ alkyl group; ² and Y ^3, together with each Y thereof The ring segment attached thereto may form a partially or fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by Y ² and Y ³ may optionally be independently selected from halogen, CN, C via one or more Group substitution of 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; each group of Y ^{2 '} and Y ^{3 '} together with the ring segments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by Y ^{2 '} and Y ^{3 '} may optionally be passed through one or more Independently 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, and C ₁ -C ₄ alkylthio Substituted; when Q is Q-1 or Q-3 and L ¹ is CD ¹ , then Y ¹ and D ¹ together with the fragments to which they are attached may form a fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by D ¹ and Y ¹ may be optionally substituted with one or more groups, such as one or two groups independently selected from Halogen, CN, OH, methyl, halomethyl, methoxy and halomethoxy; when Q 'line Q-1' or Q-3 'and the line L ⁴ CD ^4, the Y ^1' and D ⁴ together with the fragments to which they are attached may form a fully unsaturated 6-membered carbocyclic ring wherein the ring formed by D ⁴ and Y ^{1 '} may be optionally substituted with one or more groups, for example one or Two groups, independently selected from the group consisting of halogen, CN, OH, methyl, halomethyl, methoxy, and halomethoxy; when Q is Q-9 and L ¹ is CD ¹ , then R ¹² Together with D ¹ may be -(G ¹ ) _p -G ² -G ³ -; when Q' is Q-9' and L ⁴ is CD ⁴ , then R ^12' and D ⁴ may together be -(G ¹ _p -G ² -G ³ -; G ¹ , G ² and G ³ represent C(R ²¹ ) ₂ ; each R ²¹ independently of one another represents hydrogen or C ₁ -C ₄ alkyl; each p is independently of each other Represents 1 or 2; R ⁴ and R ⁵ each independently represent hydrogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxycarbonyl; R ⁶ and R ⁷ each represent hydrogen; R ⁸ and R ⁹ are each Independently from each other, hydrogen, halogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₃ - C ₄ alkenyloxy, C ₃ -C ₄ alkynyloxy C ₁ -C ₄ alkoxycarbonyl, C ₃ -C _{6 cycloalkyl, CONH 2, CONH (C 1} -C 4 alkyl), CON (C ₁ -C ₄ alkyl) _2, NH _2, NHCO ( C ₁ -C ₄ alkyl), NHCO (C ₂ -C ₄ alkenyl), NHCO (C ₂ -C ₄ alkynyl), NHCO phenyl, CHN-OH, phenyl or consists of two or four independently a 5-membered heterocyclic ring selected from the heteroatoms of O and N (provided that the heterocyclic ring does not contain contiguous oxygen atoms), wherein the alkyl group may be optionally independently selected from halo, OH via one or more , CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, benzyloxy, NH ₂ , NHCO (C ₁ -C ₄ alkyl), NHCO (C ₂ a group of -C ₄ alkenyl), NHCO (C ₂ -C ₄ alkynyl), NHCO phenyl, and phenyl, and wherein the heterocyclic ring is substituted with one or more C ₁ -C ₄ alkyl groups; ¹² and R ^{12 '} each independently represent hydrogen or C ₁ -C ₄ alkyl; R ¹³ and R ^{13 '} independently of each other represent hydrogen, C ₁ -C ₄ alkyl or C ₃ -C ₆ alkynyl.

More preferably, in this group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other represent hydrogen, halogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkyne a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkylthio group, a phenyl group or a 5-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S and N (conditions are: the heterocyclic ring does not contain adjacent oxygen atoms, adjacent sulfur atom and an oxygen or sulfur atom adjacent to), wherein the phenyl and heterocycle may be optionally substituted with one or more groups independently selected from halogen, C ₁ -C ₄ Substituted by alkoxy, C ₁ -C ₄ alkyl and C ₁ -C ₄ haloalkyl; X X-3 or X-5; Z ³ , Z ⁵ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ independently of each other represents CR ⁴ R ⁵ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ or C=CR ⁶ R ⁷ ; the Q system is selected from the group consisting of Q-1, Q-2 , Q-3 and Q-9; Q' is selected from the group consisting of Q-1', Q-2', Q-3' and Q-9'; Y ¹ , Y ² , Y ³ , Y ^{1 '} , Y ^{2 '} and Y ^{3 '} each independently represent hydrogen, halogen, C ₁ -C ₄ alkyl, C ₂ -C ₈ alkynyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio; Y ⁴ and Y ^{4 'are} each This independently represent hydrogen, halogen, OH, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio or phenyl, wherein the phenyl The group may be optionally substituted with one or more groups, for example one to five groups, independently selected from C ₁ -C ₄ alkyl groups; when Q is Q-2, Y ² and Y ³ are attached thereto The ring segment thereto may form a partially or fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by Y ^{2 '} and Y ^{3 '} may be optionally independently selected from C ₁ -C ₄ via one or more a group of alkyl groups substituted; when Q' is a Q-2', Y ^{2 '} and Y ^{3 '} together with the ring segments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring, wherein The ring formed by Y ^{2 '} and Y ^{3 '} may be optionally substituted with one or more groups independently selected from C ₁ -C ₄ alkyl.

When Q is Q-3, Y ¹ and D ¹ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring; when Q' is Q-3', Y ^1' and D ⁴ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring; when Q is Q-9 and L ¹ is CD ¹ , then R ¹² and D ¹ may together be -( G ¹ ) _p -G ² -G ³ -; when Q' is Q-9' and L ⁴ is CD ⁴ , then R ^12' together with D ⁴ may be -(G ¹ ) _p -G ² -G ³ - G ¹ , G ² and G ³ represent a methylene group; p represents 1; R ⁴ and R ⁵ each independently represent hydrogen or a C ₁ -C ₂ alkoxycarbonyl group; and R ⁶ and R ⁷ each represent a hydrogen; R ⁸ and R ⁹ each independently represent hydrogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₁ -C ₄ alkoxy, C ₃ -C ₄ olefin a C ₁ -C ₄ alkoxycarbonyl group, CONH ₂ , CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl group is optionally independently selected from OH via one or more Substituting a C ₁ -C ₄ alkoxy group, a benzyloxy group, a NH ₂ , an NHCO phenyl group, and a phenyl group and wherein the tetrazolyl group is optionally substituted with a C ₁ -C ₄ alkyl group; R ¹² and R ^{12 'are} each independently from each other Represents a C ₁ -C ₄ alkyl; R ¹³ and R ^{13 'independently} of one another represent hydrogen, C ₁ -C ₄ alkyl or C ₃ -C ₆ alkynyl group.

Even more preferably, in this group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other represent hydrogen, halogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ Alkynyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, phenyl or 5-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S and N (conditions are : the heterocyclic ring does not contain adjacent oxygen atoms, adjacent sulfur atom and an oxygen or sulfur atom adjacent to), wherein the phenyl and heterocycle may be optionally substituted with one or more groups independently selected from halogen, C ₁ -C Substituted by a group of ₄ alkoxy, C ₁ -C ₄ alkyl and C ₁ -C ₄ haloalkyl; X series X-3 or X-5; Z ³ , Z ⁵ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ independently of each other represents CR ⁴ R ⁵ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ or C=CR ⁶ R ⁷ ; the Q system is selected from the group consisting of Q-1, Q2. Q-3 and Q-9; Q' are selected from the group consisting of Q-1', Q2', Q-3' and Q-9'; Y ¹ , Y ² , Y ³ , Y ^{1 '} , Y ^{2 '} and Y ^{3 '} each independently represent hydrogen, halogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio; the Y ⁴ and Y ^{4 'each} Independently of one another represent hydrogen, halogen, OH, C ₁ -C ₄ alkyl, C ₂ -C ₈ alkynyl group, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio or phenyl, wherein the phenyl The group may be optionally substituted with one or more groups, for example one to five groups, independently selected from C ₁ -C ₄ alkyl groups; when Q is Q-2, Y ² and Y ³ are attached thereto The ring segment thereto may form a partially or fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by Y ² and Y ³ may be optionally independently selected from C ₁ -C ₄ alkyl groups via one or more Substituted; when Q' is Q-2', Y ^{2 '} and Y ^{3 '} together with the ring segments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring, wherein Y ² The ring formed by ^' and Y ^{3 '} may be optionally substituted with one or more groups independently selected from C ₁ -C ₄ alkyl.

When Q is Q-3, Y ¹ and D ¹ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring; when Q' is Q-3', Y ^1' and D ⁴ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring; when Q is Q-9 and L ¹ is CD ¹ , then R ¹² and D ¹ may together be -( G ¹ ) _p -G ² -G ³ -; when Q' is Q-9' and L ⁴ is CD ⁴ , then R ^12' together with D ⁴ may be -(G ¹ ) _p -G ² -G ³ -; G ¹ , G ² and G ³ represent a methylene group; p represents 1; R ⁴ , R ⁵ , R ⁶ and R ⁷ each represent hydrogen; and R ⁸ and R ⁹ each independently represent hydrogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₄ alkenyloxy, C ₁ -C ₄ alkoxycarbonyl, CHN-OH, tetrazolyl or diox heterocycle Pentenyl, wherein the alkyl group is optionally independently selected from OH, CN, NH _2, NHCO phenyl, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ a group substituted with a -C ₄ alkoxy group, a benzyloxy group, and a phenyl group, and wherein the tetrazolyl group is optionally substituted with a C ₁ -C ₄ alkyl group; R ¹² and R ^{12 '} each independently represent C ₁ -C ₄ alkyl; R ¹³ to R ^{13 'independently} of one another represent hydrogen, C ₁ -C ₄ alkyl or C ₃ -C ₆ alkynyl group.

Even more preferably, in this group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ , Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently represent hydrogen, halogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio.

More preferably, in this group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ , Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently represent hydrogen, halogen, methyl, ethynyl, methoxy or methylthio.

Even more preferably, in this group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ , Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} And Y ^{3 '} and Y ^{4 '} each independently represent hydrogen, chlorine, methyl, ethynyl, methoxy or methylthio.

Most preferably, in this group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ , Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^3' and Y ^4' each independently represent hydrogen, methoxy or methylthio.

Most preferably, in this group of compounds, R ¹³ and R ^13' independently of each other represent hydrogen, methyl or ethynyl.

In another group of compounds, D ¹ , D ² , D ³ and D ⁴ independently of each other represent hydrogen, hydrogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkynyl, CN, C ₁ -C ₄ alkane Thio or C ₁ -C ₄ alkoxy, wherein the alkyl and alkoxy are optionally substituted by one or more groups, for example one to five groups, independently selected from halogen, CN, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy; D ⁵ and D ⁶ independently of each other represent hydrogen, halogen, CN, NO ₂ , C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl , C ₂ -C ₈ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, phenyl, containing one to three independently selected from O, S and a 5- or 6-membered heterocyclic ring of a hetero atom of N (provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms, such as a heterocycle as defined herein, Preferred is furyl, thiophenyl or pyrazolyl), COR ¹ , OR ² , SH, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfinyl, C ₁ -C ₈ alkane Sulfosyl, phenylthio, phenylsulfinyl, phenylsulfonyl, N(R ³ ) ₂ , CO ₂ R ² , O(CO)R ¹ , CON(R ³ ) ₂ , NR ³ COR ¹ or CR ¹ N-OR ² , wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and heterocyclic ring are optionally substituted by one or more groups, for example one to five groups, independently selected from Halogen, CN, NH ₂ , NO ₂ , OR ² , C ₁ -C ₄ alkyl and C ₁ -C ₄ haloalkyl; X represents X-3, X-4 or X-5; Z ³ , Z ⁵ , Z ⁶ , Z ⁷ , Z ⁸ , Z ⁹ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ independently of each other represent CR ⁴ R ⁵ or C=CR ⁶ R ⁷ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ , SiR ¹⁰ R ¹¹ , C=O or C=CR ⁶ R ⁷ ; Q is selected from the group consisting of Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7, Q-8 and Q-9; Q' is selected from the group consisting of Q-1', Q-2', Q-3', Q-4 ', Q-5', Q-6', Q-7', Q-8' and Q-9'; Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^4' each independently represent hydrogen, halogen, OH, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio or benzene group, wherein the phenyl is optionally substituted with one or more groups, for example one to five groups independently selected from halogen, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ - Substituted alkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy group; when Q line Q-1, Q-2, Q-3, Q-4, Q-6 or Q-7, the Y ¹ and Y ² , Y ² and Y ³ , or Y ³ and Y ⁴ independently of each other together with the ring segment to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or contain one to a 5- to 7-membered heterocyclic ring independently selected from N and N(R ³ ) heteroatoms, and wherein the ring formed by Y ¹ and Y ² , Y ² and Y ³ , or Y ³ and Y ⁴ Optionally, one or more independently 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, Substitution of C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ alkylthio; when Q' is Q-1', Q-2', Q-3', Q-4', Q-6' Or Q-7', Y ^{1 '} and Y ^{2 '} , Y ^{2 '} and Y ^{3 '} , or Y ^{3 '} and Y ^{4 '} independently of each other together with the ring fragment to which they are attached may form part or not at all a saturated 5- to 7-membered carbocyclic ring or a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from N and N(R ³ ), and wherein Y ^{1 '} and Y ^{2 '} Rings formed by Y ^{2 '} and Y ^{3 '} , or Y ^3' and Y ^4' may optionally be separated by one or more Selected 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 Substitution of a _1- C ₄ alkylthio group.

When Q is Q-1, Q-3, Q-4, Q-7 or Q-8 and L ¹ is CD ¹ , then Y ¹ and D ¹ together with the fragments to which they are attached may form part or all An unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by D ¹ and Y ¹ may be optionally substituted with one or more groups, for example one to five groups, independently selected from halo, CN, 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; when Q system Q- When 1', Q-3', Q-4', Q-7' or Q-8' and L ⁴ is CD ⁴ , then Y ¹ 'and D ⁴ together with the fragments to which they are attached may form part or a fully unsaturated 5- to 7-membered carbocyclic ring wherein the ring formed by D ¹ and Y ¹ may be optionally substituted with one or more groups, for example one to five groups, independently selected from halo, CN , 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; when Q system Q -9 and L ¹ is CD ¹ , then R ¹² and D ¹ may together be -(G ¹ ) _p -G ² -G ³ -; when Q' is Q-9' and L ⁴ is CD ⁴ , then R ^{12 'and} D ⁴ may together are _{^{- (G 1) p -G 2}} -G 3 -; G 1, G 2 to G ³ represents C (R ²¹⁾ _2, wherein each R ²¹ independently represents hydrogen, halogen, C ₁ -C ₄ alkyl each other, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy groups or C ₁ -C ₄ haloalkoxy; each p independently of 1 or 2; each R ¹ independently of ^one another represents hydrogen, C ₁ -C ₄ alkyl or phenyl, wherein the alkyl and phenyl are optionally Substituted by one or more groups independently selected from the group consisting of halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, and C ₁ -C ₄ haloalkoxy; R ² independently of each other 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 halo An alkynyl, phenyl, benzyl or pyridyl group, wherein the phenyl, benzyl and pyridyl groups are optionally independently selected from halo, CN, NH ₂ , NO ₂ , OH, C ₁ - Substituted by a C ₄ alkyl group, a C ₁ -C ₄ -haloalkyl group, a C ₁ -C ₄ alkoxy group, and a C ₁ -C ₄ haloalkoxy group; each R ³ independently represents hydrogen or C ₁ -C ₄ alkyl; wherein when two R ³ groups attached to the same nitrogen atom, such groups may be the same or different; and which When two R ³ groups attached to the same nitrogen atom, these two radicals together with the nitrogen atom to which they are attached to form a ring which may be B-1, B-2, B-3, B-4 , or B-5, wherein the ring formed may be optionally substituted by one or more groups, for example one to five groups, independently selected from halogen, methyl or halomethyl; R ⁴ and R ⁵ are each Independently represents hydrogen, halogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₃ -C _{a 4} -alkenyloxy group, a C ₁ -C ₄ alkoxycarbonyl group, a C ₃ -C ₆ cycloalkyl group, CON(R ³ ) ₂ , NH ₂ , NR ³ COR ¹ or CR ¹ N-OR ² , wherein the alkyl group An alkenyl group, an alkynyl group, optionally, one or more independently selected from the group consisting of halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, a C ₁ -C ₄ haloalkoxy group and a group of NH ₂ are substituted; R ⁶ and R ⁷ each independently represent hydrogen, halogen, methyl or halomethyl; and R ⁸ and R ⁹ each independently represent hydrogen and halogen. , CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₃ -C ₄ alkenyloxy, C ₃ -C ₄ alkynyloxy , C ₁ -C ₄ alkoxycarbonyl, C ₃ -C _{6 cycloalkyl, CONH 2, CONH (C 1} -C 4 alkyl), CON (C ₁ -C ₄ alkyl) _2, NH _2, NHCO (C ₁ -C ₄ alkyl), NHCO (C ₂ -C ₄ alkenyl), NHCO (C ₂ -C ₄ alkynyl), NHCO phenyl, CHN-OH, phenyl or contains two or four independent a 5-membered heterocyclic ring selected from the heteroatoms of O and N (provided that the heterocyclic ring does not contain contiguous oxygen atoms), wherein the alkyl group is optionally independently selected from halogen, by one or more OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, benzyloxy, NH ₂ , NHCO (C ₁ -C ₄ alkyl), NHCO (C Substituted with a group of _2- C ₄ alkenyl), NHCO (C ₂ -C ₄ alkynyl), NHCO phenyl and phenyl and wherein the heterocyclic ring is substituted by one or more C ₁ -C ₄ alkyl groups.

R ¹⁰ and R ¹¹ each independently represent hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or phenyl, wherein the phenyl may optionally be passed through one or more a group substituted, for example one to five groups, independently selected from the group consisting of halogen, CN, methyl, halomethyl, methoxy and halomethoxy; R ¹² and R ^12' independently of each other represent 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 ² O)carbonyl (C ₁ -C _4- alkyl), wherein the alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, and pyridyl groups are optionally substituted with one or more groups, for example one to five groups, independently selected from halo , CN, OR ² , 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 and pyridyl; R ¹³ and R ^{13 '} independently of each other represent C ₁ -C ₄ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl or benzyl, wherein the alkyl The alkenyl, alkynyl and benzyl groups may be optionally substituted by one or more groups, for example one to five groups, independently selected from halogen, CN, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy.

More preferably, in this group of compounds, D ¹ , D ² , D ³ and D ⁴ independently of each other represent hydrogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkynyl, CN, C ₁ -C ₄ alkylthio or C ₁ -C ₄ alkoxy; D ⁵ and D ⁶ independently of each other represent hydrogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkynyl _, C ₁ -C ₄ alkoxy, a C ₁ -C ₄ alkylthio group, a phenyl group or a 5-membered heterocyclic ring containing one to three hetero atoms independently selected from O, S and N (provided that the heterocyclic ring does not contain an adjacent oxygen atom, abutting a sulfur atom or an adjacent sulfur and oxygen atom), wherein the phenyl group and the heterocyclic ring are optionally independently selected from halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl via one or more And a group substituted with a C ₁ -C ₄ haloalkyl group; X represents X-3 or X-5; Z ³ , Z ⁵ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ independently of each other represent CR ⁴ R ⁵ or C =CR ⁶ R ⁷ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ or C=CR ⁶ R ⁷ ; the Q system is selected from the group consisting of Q-1, Q-2, Q-3 And Q-9; Q' is selected from the group consisting of Q-1', Q-2', Q-3', and Q-9'; Y ¹ , Y ² , Y ³ , Y ^4, , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} are each This independently represents hydrogen, halogen, OH, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio or phenyl, wherein the phenyl Optionally substituted with one or more groups independently selected from C ₁ -C ₄ alkyl; each group of Y ² and Y ³ together with the ring segments to which they are attached may form partially or fully unsaturated a 6-membered carbocyclic ring wherein the ring formed by Y ² and Y ³ is optionally independently selected from halo, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C _a group substituted with ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ alkylthio; each group of Y ^{2 '} and Y ^{3 '} together with the ring segments to which they are attached may Forming a partially or fully unsaturated 6-membered carbocyclic ring wherein the ring formed by Y ^{2 '} and Y ^{3 '} can be optionally selected from one or more independently selected from the group consisting of halogen, CN, C ₁ -C ₄ alkyl, a group substituted with 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; when the Q system is Q-1 or Q-3 and when L ¹ based CD ^1, then D ¹ and Y ¹ together with their attached thereto fragment may be formed fully unsaturated 6-membered carbocyclic ring, wherein the D ¹ and Y ¹ form Rings may be optionally substituted by one or more groups, such as one or two groups, independently selected from halo, CN, OH, methyl, halomethyl, methoxy, and halomethoxy. ; when Q 'line Q-1' or Q-3 'and the line L ⁴ CD ^4, then Y ^1' and D ⁴ together with their attached thereto fragment may be formed fully unsaturated 6-membered carbocyclic ring, The ring formed by D ⁴ and Y ^{1 '} may be optionally substituted by one or more groups, for example one or two groups, independently selected from halogen, CN, OH, methyl, halomethyl, Methoxy and halogenated methoxy; when Q is Q-9 and L ¹ is CD ¹ , then R ¹² and D ¹ may together be -(G ¹ ) _p -G ² -G ³ -; when Q' When Q-9' and L ⁴ are CD ⁴ , then R ^{12 '} and D ⁴ may together be -(G ¹ ) _p -G ² -G ³ -; G ¹ , G ² and G ³ represent C (R ²¹ ₂ ; each R ²¹ independently of each other represents hydrogen or C ₁ -C ₄ alkyl; each p independently of 1 or 2; R ⁴ and R ⁵ each independently represent hydrogen, C ₁ -C ₄ alkane Or C ₁ -C ₄ alkoxycarbonyl; R ⁶ and R ⁷ each represent hydrogen; R ⁸ and R ⁹ each independently represent hydrogen, halogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₃ -C ₄ alkenyloxy, C ₃ -C ₄ alkynyloxy, C ₁ -C ₄ alkoxycarbonyl , C ₃ -C ₆ cycloalkyl, CONH ₂ , CONH(C ₁ -C ₄ alkyl), CON(C ₁ -C ₄ alkyl) ₂ , NH ₂ , NHCO (C ₁ -C ₄ alkyl), NHCO (C ₂ -C ₄ alkenyl), NHCO (C ₂ -C ₄ alkynyl), NHCO phenyl, CHN-OH, phenyl or two or four heteroatoms independently selected from O and N a 5-membered heterocyclic ring (provided that the heterocyclic ring does not contain contiguous oxygen atoms), wherein the alkyl group is optionally independently selected from halo, OH, CN, C ₁ -C ₄ alkane by one or more Base, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, benzyloxy, NH ₂ , NHCO (C ₁ -C ₄ alkyl), NHCO (C ₂ -C ₄ alkenyl), NHCO ( Substituted with a C ₂ -C ₄ alkynyl group, an NHCO phenyl group, and a phenyl group, and wherein the heterocyclic ring is substituted with one or more C ₁ -C ₄ alkyl groups; R ¹² and R ^{12 '} are each independently of each other Represents hydrogen or C ₁ -C ₄ alkyl; R ¹³ and R ^13' independently of each other represent hydrogen, C ₁ -C ₄ alkyl or C ₃ -C ₆ alkynyl.

Even more preferably, in this group of compounds, D ¹ , D ² , D ³ and D ⁴ each represent hydrogen, halogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ Alkoxy or C ₁ -C ₄ alkylthio; D ⁵ and D ⁶ independently of each other represent hydrogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C _{a 1-} C ₄ alkylthio group, a phenyl group or a 5-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S and N (provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous a sulfur atom or an adjacent sulfur and oxygen atom), wherein the phenyl group and the heterocyclic ring are optionally independently selected from one or more of the group consisting of halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl, and a group substituted with a C ₁ -C ₄ haloalkyl group; X series X-3 or X-5; Z ³ , Z ⁵ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ independently of each other represent CR ⁴ R ⁵ ; Z ⁴ And Z ¹² represents CR ⁸ R ⁹ or C=CR ⁶ R ⁷ ; the Q system is selected from the group consisting of Q-1, Q-2, Q-3, and Q-9; Q' Selected from the group consisting of Q-1', Q-2', Q-3', and Q-9'; Y ¹ , Y ² , Y ³ , Y ^{1 '} , Y ^{2 '} and Y ^{3 'is} each independently represent hydrogen or C ₁ -C ₄ Alkyl; Y ⁴ and Y ^{4 '} each independently represent hydrogen, halogen, OH, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ An alkylthio group or a phenyl group, wherein the phenyl group may be optionally substituted with one or more groups, for example one to five groups, independently selected from C ₁ -C ₄ alkyl groups; when Q is Q-2 , Y ² and Y ³ together with the ring segments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by Y ^{2 '} and Y ^{3 '} may optionally be passed through one or more Substituents independently selected from C ₁ -C ₄ alkyl; when Q' is Q-2', Y ^{2 '} and Y ^{3 '} together with the ring segments to which they are attached may form part or not at all A saturated 6-membered carbocyclic ring wherein the ring formed by Y ^{2 '} and Y ^{3 '} can be optionally substituted with one or more groups independently selected from C ₁ -C ₄ alkyl.

When Q is Q-3, Y ¹ and D ¹ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring; when Q' is Q-3', Y ^1' and D ⁴ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring; when Q is Q-9 and L ¹ is CD ¹ , then R ¹² and D ¹ may together be -( G ¹ ) _p -G ² -G ³ -; when Q' is Q-9' and L ⁴ is CD ⁴ , then R ^12' together with D ⁴ may be -(G ¹ ) _p -G ² -G ³ - G ¹ , G ² and G ³ represent a methylene group; p represents 1; R ⁴ and R ⁵ each independently represent hydrogen or a C ₁ -C ₂ alkoxycarbonyl group; and R ⁶ and R ⁷ each represent a hydrogen; R ⁸ and R ⁹ each independently represent hydrogen, CN, OH, CHO, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₁ -C ₄ alkoxy, C ₃ -C ₄ olefin a C ₁ -C ₄ alkoxycarbonyl group, CONH ₂ , CHN-OH, tetrazolyl or dioxolyl, wherein the alkyl group is optionally independently selected from OH via one or more Substituting a C ₁ -C ₄ alkoxy group, a benzyloxy group, a NH ₂ , an NHCO phenyl group, and a phenyl group and wherein the tetrazolyl group is optionally substituted with a C ₁ -C ₄ alkyl group; R ¹² and R ^{12 'are} each independently from each other Represents a C ₁ -C ₄ alkyl; R ¹³ and R ^{13 'independently} of one another represent hydrogen, C ₁ -C ₄ alkyl or C ₃ -C ₆ alkynyl group.

More preferably, in this group of compounds, D ¹ , D ² , D ³ and D ⁴ each represent hydrogen, halogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ Alkoxy or C ₁ -C ₄ alkylthio; D ⁵ and D ⁶ independently of each other represent hydrogen, halogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy a C ₁ -C ₄ alkylthio group, a phenyl group or a 5-membered heterocyclic ring containing one to three hetero atoms independently selected from O, S and N (provided that the heterocyclic ring does not contain an adjacent oxygen atom, Adjacent sulfur atom or contiguous sulfur and oxygen atom), wherein the phenyl group and the heterocyclic ring are optionally independently selected from one or more of halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkane a group substituted with a C ₁ -C ₄ haloalkyl group; X series X-3 or X-5; Z ³ , Z ⁵ , Z ¹⁰ , Z ¹¹ , Z ¹³ and Z ¹⁴ independently of each other represent CR ⁴ R ⁵ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ or C=CR ⁶ R ⁷ ; the Q group is selected from the group consisting of Q-1, Q2, Q-3 and Q-9; Q' is selected from the group consisting of: Q-1 ', Q2' , Q-3 ' , and ^{Q-9'; Y 1,} Y 2, Y 3, Y 1 ', Y 2' and Y ^{3 'independently} of one another represent hydrogen or C ₁ -C ₄ Group; Y ⁴ and Y ^{4 'are} each independently of one another represent hydrogen, halogen, OH, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkoxy Thio or phenyl, wherein the phenyl group may be optionally substituted by one or more groups, for example one to five groups, independently selected from C ₁ -C ₄ alkyl groups; when Q is Q-2, Y ² and Y ³ together with the ring segments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring, wherein the ring formed by Y ² and Y ³ may optionally be independently or in one or more Substituted with a group selected from C ₁ -C ₄ alkyl; when Q' is Q-2', Y ^{2 '} and Y ^{3 '} together with the ring segments to which they are attached may form partially or fully unsaturated 6 a carbocyclic ring wherein the ring formed by Y ^{2 '} and Y ^{3 '} can be optionally substituted with one or more groups independently selected from C ₁ -C ₄ alkyl. \When Q is Q-3, Y ¹ and D ¹ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring; when Q' is Q-3', Y ^1' And D ⁴ together with the fragments to which they are attached may form a partially or fully unsaturated 6-membered carbocyclic ring; when Q is Q-9 and L ¹ is CD ¹ , then R ¹² and D ¹ may together be - (G ¹ ) _p -G ² -G ³ -; when Q' is Q-9' and L ⁴ is CD ⁴ , then R ^12' together with D ⁴ may be -(G ¹ ) _p -G ² -G ³ -; G ¹ , G ² and G ³ represent a methylene group; p represents 1; R ⁴ , R ⁵ , R ⁶ and R ⁷ each represent hydrogen; and R ⁸ and R ⁹ each independently represent hydrogen, CN, OH , CHO, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₄ alkenoxy, C ₁ -C ₄ alkoxycarbonyl, CHN-OH, tetrazolyl or dioxa Cyclopentenyl, wherein the alkyl group is optionally independently selected from OH, CN, NH ₂ , NHCO phenyl, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C Substituted with a group of ₁ -C ₄ alkoxy, benzyloxy and phenyl, and wherein the tetrazolyl group is optionally substituted by C ₁ -C ₄ alkyl; R ¹² and R ^{12 '} are each independently represented C ₁ -C ₄ alkyl group; R ¹³ to R ^{13 'independently} of one another represent hydrogen, C ₁ -C ₄ alkyl or C ₃ -C ₆ alkynyl group.

Even more preferably, in this group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ , Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently represent hydrogen, halogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio.

Even more preferably, in this group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ , Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently represent hydrogen, halogen, methyl, ethynyl, methoxy or methylthio.

Even more preferably, in this group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ , Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ² ' And Y ^{3 '} and Y ^{4 '} each independently represent hydrogen, chlorine, methyl, ethynyl, methoxy or methylthio.

Most preferably, in this group of compounds, D ¹ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ , Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^{1 '} , Y ^{2 '} , Y ^3' and Y ^4' each independently represent hydrogen, methoxy or methylthio.

Most preferably, in this group of compounds, R ¹³ and R ^13' independently of each other represent hydrogen, methyl or ethynyl.

Novel compounds of formula (I) also form part of the invention. Accordingly, in a further aspect, the invention provides a compound of formula I as defined above, wherein X is X-3, X-4 or X-5 and the compound of formula I is not a compound of formula I'

Wherein R ^a is hydrogen or phenyl, R ^b is a primary alkyl group and n is 4 or 5; and the compound of formula I is not a compound of formula I"

Wherein each R ^{c is} independently hydrogen or methyl; and the compound of formula I is not a compound of formula I'''a, I'''b or I'''c

And the compound of formula I is not a compound of formula I''' Wherein n is 3, R ^d and R ^e are all methyl, R ^f and R ^g are all hydrogen; or n is 3, R ^d and R ^e are both p-methoxyphenyl, R ^f and R ^g are Hydrogen; or n series 4, R ^d and R ^e are all hydrogen, R ^f and R ^g are all hydrogen; or n is 4, R ^d and R ^e are all p-methylphenyl, R ^f and R ^g are Hydrogen; or n-system 4, R ^d and R ^e are And R ^f and R ^g are both hydrogen; or n is 4, R ^d and R ^e are both n-butyl, R ^f and R ^g are all hydrogen; or n is 4, R ^d and R ^e are all hydrogen, R ^f and R ^g are all hydrogen; or n is 4, R ^d and R ^e are all p-hydroxyphenyl, R ^f and R ^g are all hydrogen; or n is 4, R ^d and R ^e are all p-methoxy Phenyl, R ^f and R ^g are all hydrogen; or n is 5, R ^d and R ^e are both n-butyl, R ^f and R ^g are all hydrogen; or n is 4, R ^d and R ^e are all hydrogen , R ^f and R ^g are all p-methoxyphenyl groups; or in a group of compounds of the invention, when Q is Q-4, Q-7 or Q-8 and L ¹ is CD ¹ and Q is not Q- At 1 o'clock, then Y ¹ and D ¹ together with the fragments to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or partially or fully unsaturated, containing one to three independently selected from a 5- to 7-membered heterocyclic ring of a hetero atom of O, S, N and N(R ³ ) (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 D ¹ and Y ¹ is optionally independently selected from halogen, CN, NH ₂ , NO ₂ , OH, C via one or more _a group substitution of _1- C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, and C ₁ -C ₄ haloalkoxy (ie, when Q is Q-1, Y ¹ and D ¹ does not form a ring together; R ⁸ represents hydrogen, halogen, CN, OH, SH, CHO, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkenyl, C ₁ -C ₆ alkynyl, C ₁ - C ₆ alkoxy, C _{1 -C6} alkenyloxy, C ₁ -C ₆ alkynyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio, C ₃ -C ₆ cycloalkyl, a phenyl 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 contiguous oxygen atoms, contiguous sulfur atoms or contiguous Sulfur and an oxygen atom), wherein the alkyl, alkenyl, alkynyl, phenyl and heterocyclic ring are optionally substituted by one or more groups, for example one to five groups, independently selected from halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio and C ₁ -C ₄ Halogenated alkylthio; when Q is Q-1, Y ⁴ represents 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, COR ¹ , OR ² , SH, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfinyl, C ₁ -C ₈ alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonate Anthracenyl, N(R ³ ) ₂ , CO ₂ R ² , O(CO)R ¹ , CON(R ³ ) ₂ , NR ³ COR ¹ , CR ¹ N-OR ² , wherein the alkyl group, cycloalkyl group, Alkenyl, alkynyl, phenyl may be optionally substituted by one or more groups, for example one to five groups, independently selected from halo, CN, NH ₂ , NO ₂ , OR ² , C ₁ -C ₄ An alkyl group, a C ₁ -C ₄ haloalkyl group, and a C ₁ -C ₄ alkylthio group; or Y ⁴ together with Y ³ and together with the fragments to which they are attached may form a partially or fully unsaturated 5- to 7-membered Carbocyclic or partially or fully unsaturated 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, N and N(R ³ ) (provided that the heterocyclic ring is not Containing contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms), and wherein the ring formed by Y ³ and Y ⁴ may be optionally substituted with one or more groups, for example one to five groups, independently selected 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.

In a group of compounds, one of Q and Q' along with the fragment to which it is attached is not phenanthroline. In a group of compounds, R ⁸ and R ^{9 are} different alkoxycarbonyl groups. In a group of compounds, when Q is Q-1, Y ⁴ is not a heterocyclic ring. In a group of compounds, one of Q and Q' together with the fragment to which it is attached is not a morphine, R ⁸ and R ^{9 are} not alkoxycarbonyl, and when Q is Q-1, Y ⁴ Not a heterocyclic ring.

Preferred substituent definitions for the novel compounds of the invention are the same as described above.

Compounds of formula I' are disclosed in JP 10113541. Compounds of formula I" are disclosed in Inorganic Chemistry, 1983, 22(1), 171-174. Compounds of formula I''' are disclosed in the Journal of Medicinal Chemistry, 1975, 18(11), 1088-94). Compounds of formula I''' are disclosed in the following publications: Inorganic Chemistry, 2010, 49(9), 4023-4035); Synthetic Reagents e-EROS Encyclopedia (publisher: John Wiley Co., Ltd., Essex, UK) (e-EROS Encyclopedia of Reagents for Organic Synthesis (2001), publisher: John Wiley and Sons, Ltd, Chichester, UK ); Journal of the American Chemical Society, 1999, 121 (15), 3784-3692; Chemistry Letters (1997, 7, 615-616); Journal of Analytical Chemistry (Analytica) Chemica Acta, 1996, 329(1-2), 57-64); The German Journal of Applied Chemistry, Angewandte Chemie, International Edition in English, 1996, 35(8), 906-909); Journal of the American Chemical Society, 1996, 118(13), 3285-6; New Chemistry Journal (New Journal of Chemistry, 1995, 19 (4), 409-26); "Purs and Applied Chemistry 1995, 67 (2), 233-40); "Chemistry Letters" (1994, 3, 397- 400); Journal of the American Chemical Society, 1993, 115 (24), 11237-44; Journal of the Chemical Society, Chemical Communications, 1993, 9, 801 -4); New Journal of Chemistry, 1992, 16(10), 931-42; Tetrahedron Letters, 1992, 33(25), 3625-8; Germany Journal of Applied Chemistry (Angewandte Chemie, 1989, 101(2), 192-4).

Optionally, the present invention may not include a compound in which at least one of L ⁵ and L ¹ and L ² is nitrogen, and/or L ⁶ nitrogen and at least one of L ³ and L ⁴ is nitrogen. For example, a 6-membered heterocyclic ring on either side of X may not include =NC=CN=structural component. Optionally, the present invention may not require such of formula I '''' compounds, where R ^d and R ^e or hydrocarbon-based hydrogen and R ^f and R ^g based hydrogen. Optionally, the present invention may not require such a compound of formula I, i.e., wherein when X is X-3, R ⁸ and R ⁹ together are not C=O. Nos. 3,498,981, WO 2009/047584, and JP 10113541 are hereby incorporated herein by reference.

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

In another aspect, the invention provides a compound having the chemical formula Int-1

Wherein X' represents -CH=CH-CH ₂ - or CH ₂ -CH=CH- and Q, Q', L ¹ , L ² , L ³ , L ⁴ , L ⁵ and L ⁶ are as defined for the formula (I) As defined by the compound, or a salt or N-oxide thereof. The preferred definitions of Q, Q', L ¹ , L ² , L ³ L ⁴ , L ⁵ and L ⁶ as defined for the compounds of formula (I) also apply to compounds of formula (Int-1).

In another aspect, the invention provides a compound having the chemical formula Int-2

Wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ and X are as defined herein for a compound of formula (I); or a salt or N -oxide thereof. The preferred definitions of L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ and X as defined for the compounds of formula (I) also apply to compounds of formula (Int-2). Particularly preferred are compounds having the formula (int-2) wherein each of L ¹ , L ² , L ³ , L ⁴ , L ⁵ and L ⁶ is CH.

In another aspect, the invention provides a compound having the chemical formula Int-3

Wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Q and X are as defined for the compound of formula (I); or a salt or N -oxide thereof. The preferred definitions of L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Q and X as defined for the compounds of formula (I) also apply to compounds of formula (Int-3).

In another aspect, the invention provides a compound having the chemical formula Int-4

Wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Q and X are as defined for the compound of formula (I); or a salt or N -oxide thereof. The preferred definitions of L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Q and X as defined for the compounds of formula (I) also apply to compounds of formula (Int-4).

In another aspect, the invention provides a compound having the chemical formula Int-5

Wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Q and X are as defined for a compound of formula (I) and the R ²⁹ halogen is specifically chlorine, bromine or iodine; Salt or N-oxide. The preferred definitions of L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Q and X as defined for the compounds of formula (I) also apply to compounds of formula (Int-4).

The compounds of formula (I) can exist as different geometric or optical isomers or in different tautomeric forms. These can be separated or isolated by known techniques (usually chromatography), and all such isomers as well as tautomers and their Mixtures in all ratios, along with isotopic forms, such as deuterated compounds, are part of the present invention. The compounds of the invention also include salts or N-oxides of the compounds of the invention.

Table 1. Illustrative embodiments of the following compounds

The compounds in Table 2 illustrate compounds of formula (I).

The compounds of Table 2 include all isomers, tautomers, and mixtures thereof.

In one embodiment of the invention, a plurality of compounds of formula IA are provided:

Wherein Q, Q', D ¹ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ and X are as defined for the compound of formula I. The preferred definitions of Q, Q', D ¹ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ and X are the same as for the corresponding substituents of formula I.

In one embodiment the invention provides a compound of formula IB

Wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , R ¹² , R ^{12 '} , R ¹³ , R ^{13 '} and X are as defined for the compound of formula I. The preferred definitions of L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , R ¹² , R ^{12 '} , R ¹³ , R ^{13 '} and X are the same as for the corresponding substituents of formula I.

In one embodiment the invention provides a plurality of compounds having the formula IC

Wherein R ¹² , R ^{12 '} , R ¹³ , R ^{13 '} , D ¹ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ and X are as defined for the compound of formula I. The preferred definitions of R ¹² , R ^{12 '} , R ¹³ , R ^{13 '} , D ¹ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ and X are the same as for the corresponding substituents of formula I.

In one embodiment the invention provides a plurality of compounds having the formula ID

Wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Y ¹ , Y ^{1 '} , Y ² , Y ^{2 '} , Y ³ , Y ^{3 '} , Y ⁴ , Y ^{4 '} and X For the definition of a compound of formula I. Preferably, L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Y ¹ , Y ^{1 '} , Y ² , Y ^{2 '} , Y ³ , Y ^{3 '} , Y ⁴ , Y ^{4 '} and X The definition is the same as for the corresponding substituent of formula I.

In one embodiment the invention provides a compound of formula IE

Wherein Y ¹ , Y ^{1 '} , Y ² , Y ^{2 ′} , Y ³ , Y ^{3 ′} , Y ⁴ , Y ^{4 ′} , D ¹ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ and X are as For the definition of a compound of formula I. Y ¹ , Y ^{1 '} , Y ² , Y ^{2 ′} , Y ³ , Y ^{3 ′} , Y ⁴ , Y ^{4 ′} , D ¹ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ and X are preferred. The definition is the same as for the corresponding substituent of formula I.

In one embodiment the invention provides a plurality of compounds of formula IF

Wherein Y ¹ , Y ² , Y ³ , Y ⁴ , R ^{12 ′} , R ^{13 ′} , L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ and X are as defined for the compound of formula I . Preferred definitions of Y ¹ , Y ² , Y ³ , Y ⁴ , R ^{12 ′} , R ^{13 ′} , L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ and X and for the formula I The corresponding substituents are the same.

In one embodiment the invention provides a compound of formula IG

Wherein Y ¹ , Y ² , Y ³ , Y ⁴ , R ^{12 ′} , R ^{13 ′} , D ¹ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ and X are as defined for the compound of formula I of. Preferred definitions of Y ¹ , Y ^{1 '} , Y ² , Y ^{2 '} , R ^{12 ′} , R ^{13 ′} , D ¹ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ and X The corresponding substituents of I are the same.

In one embodiment the invention provides a compound of formula IH

Wherein Y ² , Y ^{2 '} , Y ³ , Y ^{3 '} , Y ⁴ , Y ^{4 '} , L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ and X are as for a compound of formula I Defined. Preferred definitions of Y ² , Y ^{2 ′} , Y ³ , Y ^{3 ′} , Y ⁴ , Y ^{4 ′} , L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ and X The corresponding substituents are the same.

In one embodiment the invention provides a compound of formula IJ

Wherein Y ² , Y ^{2 '} , Y ³ , Y ^{3 '} , Y ⁴ , Y ^{4 '} , D ¹ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ and X are as for a compound of formula I Defined. Preferred definitions of Y ² , Y ^2′ , Y ³ , Y ^3′ , Y ⁴ , Y ^4′ , D ¹ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ and X The corresponding substituents are the same.

In one embodiment the invention provides a compound of formula IK

Wherein Q, Q', D ² , D ³ , D ⁵ , D ⁶ and X are as defined for the compound of formula I. The preferred definitions of Q, Q', D ² , D ³ , D ⁵ , D ⁶ and X are the same as for the corresponding substituents of formula I.

In one embodiment the invention provides a compound of formula IL

Wherein Q, Q', D ² , D ³ , D ⁴ , D ⁵ , D ⁶ and X are as defined for the compound of formula I. The preferred definitions of Q, Q', D ² , D ³ , D ⁴ , D ⁵ , D ⁶ and X are the same as for the corresponding substituents of formula I.

In one embodiment the invention provides a compound of formula IM

Wherein Y ¹ , Y ² , Y ³ , Y ⁴ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ , Q′ and X are as defined for the compound of formula I. The preferred definitions of Y ¹ , Y ^{1 '} , Y ² , Y ^{2 '} , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ , Q′ and X are the same as for the corresponding substituents of formula I.

In one embodiment the invention provides a compound of formula IN

Wherein Y ¹ , Y ² , Y ^{2 ′} , Y ³ , Y ^{3 ′} , Y ⁴ , Y ^{4 ′} , L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ and X are as defined for The compound is defined. Preferred definitions and pairs for Y ¹ , Y ² , Y ^{2 ′} , Y ³ , Y ^{3 ′} , Y ⁴ , Y ^{4 ′} , L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ and X The same is true for the corresponding substituent of formula I.

In one embodiment the invention provides a compound of formula IO

Wherein Y ¹ , Y ² , Y ^{2 ′} , Y ³ , Y ^{3 ′} , Y ⁴ , Y ^{4 ′} , D ¹ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ and X are as defined for The compound is defined. Preferred definitions of Y ² , Y ^2′ , Y ³ , Y ^3′ , Y ⁴ , Y ^4′ , D ¹ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ and X The corresponding substituents are the same.

The compounds of the invention can be made by a variety of methods as illustrated in Schemes 1-16. The compounds described in these schemes also refer to any isomer or tautomer, especially It is a geometric isomer produced from the oxime and oxime ether moieties.

(1) A compound of the formula (Ia) wherein Z ¹ , Z ³ , Z ⁶ and Z ¹⁰ are methylene groups and X " represents X ''' -1, X ''' -2, and X ''' -3 and X ''' -4 compounds of formula (I)

It can be derived from a compound of formula (V) wherein Q, L ¹ , L ² and L ⁵ are as defined herein for a compound of formula (I) and a compound of formula (VI) wherein Q ' , L ³ , L ⁴ and L ⁶ are as defined herein for a compound of formula (I) and R ²⁸ is a halogen (especially chlorine, bromine or iodine) or a sulfonate group, such as a mesylate. , tosylate, triflate, benzenesulfonate, nitrobenzenesulfonate, or nonafluorobutyl sulfonate). The reaction is carried out in the presence of a base such as n-butyllithium, di-butyllithium, lithium diisopropylamide, sodium amide or sodium hydride. Examples of such substitution reactions can be found in Synthesis (Synthesis, (6), 519-521; 1992); Journal of the American Chemical Society, 127 (43), 15151-15160; ); "Angewandte Chemie, International Edition, 45 (6), 932-935; 2006) or "Synthesis" (Synthesis, (19), 3253-3256; 2005).

Process 2

(2) A compound of the formula (Ib) wherein Q and Q ' are the same (Q and Q ' are represented as Q in Scheme 2), Z ³ , Z ⁵ , Z ⁶ , Z ⁹ , Z ¹ and Z a compound of formula (I) wherein the ¹⁴ series is methylene and X " represents X " -1, X " -2, and X " -3

It can be derived from a compound of formula (V) wherein Q, L ¹ , L ² and L ⁵ are as defined herein for a compound of formula (I) and a compound of formula (VII) (wherein X " It is obtained here as defined for the compound of formula (Ib) and R ²⁹ is a halogen, especially chlorine, bromine or iodine. The reaction is carried out in a base such as n-butyllithium, secondary-butyl It is carried out in the presence of lithium, lithium diisopropylamide, sodium amide or sodium hydride. Examples of such substitution reactions can be found in Journal of Organometallic Chemistry, 607 (1-2), 194- 202; 2000); in the Journal of European Chemistry (Chemistry-A European Journal, 14 (2), 682-696; 2008) or "Inorganic Chemistry" (49 (9), 4023-4035; 2010).

Process 3

(3) The compound of formula (Id) is a compound of formula (I) wherein Q is the same as Q ' (Q and Q ' are represented as Q in Scheme 3), and L ¹ is the same as L ⁴ (L ¹ and L ⁴ are both expressed as L ¹ in Scheme 3), L ² is the same as L ³ (L ² and L ³ are both expressed as L ² in Scheme 3), and L ⁵ is the same as L ⁶ (L ⁵ and L ⁶ are both represented as L ⁵ in Scheme 3) and X is CH ₂ —CH ₂ —CH ₂ , which can be catalytically hydrogenated from the compound in the presence of a metal catalyst such as palladium, nickel or platinum. (IX) (wherein Q, L ¹ , L ² and L ⁵ are as defined herein for the compound of formula (I)). This reaction is usually carried out under a hydrogen atmosphere in the presence of a solvent. In some cases, it is necessary to apply a pressure in the range of 1 bar to 100 bar. A solvent suitable for such a reaction, such as methanol or ethanol, a cyclic ether, such as two Or tetrahydrofuran, or an ester such as ethyl acetate. The reaction is usually carried out at a reaction temperature ranging from 0 ° C to the boiling point of the solvent. An example of hydrogenation carried out in the presence of a nickel catalyst can be found in Journal of Organic Chemistry 69 (6), 1959-1966; 2004. An example of hydrogenation carried out in the presence of a palladium catalyst can be found in Journal of Organic Chemistry 74 (16), 6072-6076; 2009. An example of hydrogenation carried out in the presence of a platinum catalyst can be found in Organometallics, 5(2), 348-55; 1986.

(4) A compound of the formula (IX) can be produced from a compound of the formula (Ic) by a water elimination reaction, which is a compound of the formula (I) wherein Q and Q ' are the same (Q and Q ' in Scheme 3 are represented), L ¹ the same L ⁴ lines of Q, (L ¹ and L ⁴ in Scheme 3 is represented as L ^1), L ² and L ³ based same (L ² and L ³ in In Scheme 3, it is represented as L ² ), L ⁵ is the same as L ⁶ (L ⁵ and L ⁶ are both represented as L ⁵ in Scheme 3) and X is CH ₂ —CH(OH)—CH ₂ . This can be accomplished using one of a number of techniques well known to those skilled in the art, including the conversion of a hydroxyl group to a more reactive leaving group, such as, for example, a halogen (especially chlorine, bromine). Or iodine), or a sulfonate group such as mesylate, tosylate, triflate, benzenesulfonate, nitrobenzenesulfonate, or nonafluorobutyl sulfonate, And then in a suitable base (such as sodium hydroxide or potassium hydroxide, triethylamine, diisopropylamine, DBU (1,8-diazabicyclo [5.4.0] undec-7-ene) or pyridine) This leaving group is removed in the presence of. An example of this elimination reaction can be found in Bioorganic & Medicinal Chemistry Letters, 14(14), 3635-3638; 2004; Journal of the American Chemical Society, 129 (48), 14836-14837; 2007). Alternative elimination reaction procedures are known and described, for example, in "March's Advanced Organic Chemistry: Reaction, Mechanisms and Structure, Sixth Edition, 2007" and therein. In the reference.

(5) A compound of the formula (Ic) can be obtained by a chemical formula (in the presence of a base such as n-butyllithium, di-butyllithium, lithium diisopropylamide, sodium amide or sodium hydride) a compound of V) wherein Q, L ¹ , L ² and L ⁵ are as defined herein for a compound of formula (I) and a compound of formula (VIII) wherein R ³⁰ is C ₁ -C ₄ Alkyl) reaction to prepare. The reaction is usually carried out at a reaction temperature ranging from -100 ° C to 50 ° C. Suitable solvents for such reactions are, for example, cyclic ethers, such as Or tetrahydrofuran, or a hydrocarbon such as pentane, hexane, cyclohexane or toluene. Similar examples and conditions for the reaction of an anionic or organometallic compound with formic acid of formula (VIII) can be found in WO 2008088538; Tetrahedron, 66 (33), 6445-6449; 2010); Synthesis (Synthesis) , (7), 1123-1140; 2010) or "Organic Letters" (10 (23), 5321-5324; 2008). Specific examples can be found in the experimental part of this document.

For many other compounds, compounds of formula (Ic) are especially useful as intermediates in which the hydroxyl groups formed are converted to other functional groups such as carbonyl, fluorine or chlorine. Such transformations can be accomplished using a number of conditions well known to those skilled in the art.

(6) A compound of the formula (Ie) wherein the Q and Q ' are Q-2 and Q-2', respectively, of the compound of formula (I), which can be derived from the formula (23-24) using the formula (24-24) The dinitrile of X) wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ and X are as defined herein for the compound of formula (I). Specific examples can be found in the experimental part herein, wherein Q-2 and Q-2' are quinazolin-2-yl.

(7) The dinitrile of formula (X) can be prepared using the procedure 25 described herein. A more specific example is shown in Flow 5.

Process 5

(8) a dinitrile of the formula (Xa) having a compound of the formula (X), wherein the L ¹ is a CD ¹ , the L ² -based CD ² , the L ³ -based CD ³ , the L ⁴ -based CD ⁴ , and the L ⁵ -based CD ⁵ , L ⁶ is CD ⁶ and D ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ are each hydrogen, which can be in cyanide (such as trimethyldecyl cyanide, potassium cyanide or sodium cyanide) Prepared from the presence of a pyridine N-oxide of formula (XI) wherein X is as defined herein for a compound of formula (I). Such transformations are well known to those skilled in the art. Examples and specific conditions can be found in Journal of Organic Chemistry, 48 (8), 1375-7; 1983; Journal of the American Chemical Society, 130 (8), 2414 -2415; 2008); Inorganic Chemistry, 45 (10), 4088-4096; 2006).

9) A pyridine N-oxide of the formula (XI) can be oxidized from the compound (XII) in the presence of an oxidizing agent (such as mCPBA, ozone or hydrogen peroxide) (wherein the X system is as herein described for the formula (I) The compound is defined by)). Examples and specific conditions can be found in Journal of Organic Chemistry, 2000, vol. 65, #19 p. 5937-5941; Tetrahedron Letters, 51(43), 5690-5693 ;2010); International Patent Application (PCT Int. Appl.), 2010027500, 11 Mar 2010.

The following scheme demonstrates the preparation of different intermediates: Scheme 6 (for the preparation of compounds of formula (VI))

(10) The compound of the formula (VIa) is a compound of the formula (VI) wherein X ''' is X " -2 and each of Z ⁴ and Z ⁵ is a methylene group which can be derived from the formula (XIII) (wherein L ^3, L ^4, L ^6, and Q 'based as defined for compound of formula (I) as defined herein) were prepared. such conversions may be utilized skilled in the art that a number of conditions well known to be achieved. Specific examples are given in the experimental section herein.

(11) A compound of the formula (XIII) can be reduced from a metal hydride (for example, lithium aluminum hydride or diisobutylaluminum hydride) from a compound of the formula (XIV) wherein L ³ , L ⁴ , L ⁶ and Q ' is prepared as defined herein for a compound of formula (I) and R ³⁰ is C ₁ -C ₄ alkyl. Examples of such reductions can be found in the Journal of Combinatorial Chemistry, 7(6), 958-967; 2005. The reaction is usually carried out in the presence of a solvent at a temperature between -100 ° C and 20 ° C.

(12) A compound of the formula (XIV) can be obtained by a chemical formula (in the presence of a base such as n-butyllithium, di-butyllithium, lithium diisopropylamide, sodium amide or sodium hydride) a compound of XLI) wherein L ³ , L ⁴ , L ⁶ and Q ' are as defined herein for a compound of formula (I) and a compound of formula (XV) wherein R ³⁰ is C ₁ -C ₄ alkyl) reaction to prepare. The reaction is usually carried out at a reaction temperature ranging from -100 ° C to 50 ° C. Suitable solvents for such reactions are, for example, cyclic ethers, such as Or tetrahydrofuran, or a hydrocarbon such as pentane, hexane, cyclohexane or toluene.

(13) The compound of the formula (VIb) is a compound of the formula (VI) wherein X ''' is X ''' -1 wherein Z ² is a methylene group which can be derived from a compound of the formula (XLI) preparation. This can be accomplished using methods known to those skilled in the art, among which there is halogenation using chloro-, bromo- or iodine-succinimide. Examples and specific conditions can be found in Tetrahedron, 64 (27), 6358-6363; 2008); Organic Letters, 12 (11), 2551-2553; 2010); Organic & Biological Molecular Chemistry (Organic & Biomolecular Chemistry, 7 (24), 5074-5077; 2009) or "Journal of Organic Chemistry, 75 (19), 6540-6548; 2010).

(14) A compound of the formula (Ig) which is a compound of the formula (I) wherein Q is the same as Q' (Q and Q ' are represented as Q ' in Scheme 7), L ¹ and L ⁴ the same line (L ¹ to L ⁴ in Scheme 7 are denoted as L ^4), L ² identical L ³ lines (L ² and L ³ are represented in Scheme 7 is L ^3), L ⁵ and L ⁶ the same line (L ⁵ and L ⁶ are shown in Scheme 7 is L ^6), X-based X-3 or X-5, wherein ^{Z 3, Z 5, Z 10} , Z 11, Z 13 and Z ¹⁴ - line a methyl group (represented by X ''' in this scheme) and Z ⁴ and Z ¹² are CR ⁸ R ⁹ , wherein R ⁸ is H and R ⁹ is COOR ² , wherein R ² is C ₁ -C ₄ alkane a compound having the formula (If) which is a compound of the formula (I) wherein Q and Q ' are the same (Q and Q ' are represented as Q ' in Scheme 7), L ¹ and L ⁴ based same ^{(L. 1} and L ⁴ in Scheme 7 are denoted as L ^4), L ² and L ³ based same (L ² and L ³ are represented in Scheme 7 is L ^3), L ⁵ and L ⁶ based same (L ⁵ and L ⁶ are shown in Scheme 7 is L ^6), X-based X-3 or X-5, wherein ^{Z 3, Z 5, Z 10} , Z 11, Z 13 and Z ¹⁴ lines Methylene (represented by X ''' in this process) and Z ⁴ and Z ¹² CR ⁸ R ⁹ , wherein R ⁸ and R ⁹ are each COOR ² , wherein R ² is C ₁ -C ₄ alkyl). Such transformations are well known to those skilled in the art. Examples and conditions for such reactions can be found in Tetrahedron (65 (39), 8283-8296; 2009); European Journal of Organic Chemistry, (32), 5376-5385; 2007); Journal of the American Chemical Society, 126(12), 3700-3701; 2004; Bioorganic & Medicinal Chemistry Letters, 14(9), 2141 -2145; 2004) and in the Journal of Heterocyclic Chemistry, 39 (6), 1167-1171; 2002).

For many other compounds, compounds of formula (Ig) are especially useful as intermediates in which the carboxyl group is converted to other functional groups. Such transformations are well known to those skilled in the art.

(15) A compound of the formula (If) may be derived from a compound of the formula (VI) with a dialkyl C of the formula (XXXIII) in the presence of a base such as potassium carbonate or sodium carbonate, sodium or sodium hydride. The diester (wherein R ² is a C ₁ -C ₄ alkyl group) is prepared.

Both compounds of the formula (If) are known and are given in the table below. Their preparation is disclosed in Inorganic Chemistry, 1983, 22, 171-174. A similar procedure can be used to prepare other compounds of formula (If).

(16) A compound of the formula (Ij) which is a compound of the formula (I) wherein the X system X-3 and Z ³ , Z ⁴ and Z ⁵ are each a methylene group may be derived from the formula (Ih) a compound (which is a compound of formula (I) wherein X is X-3 and Z ⁴ and Z ⁵ are each methylene, and Z ³ is CR ⁴ R ⁵ , wherein R ⁵ is hydrogen and R ⁴ is CO ₂ R ² wherein R ² is C ₁ -C ₄ alkyl) is prepared. Such decarboxylation can be accomplished using a number of conditions well known to those of ordinary skill in the art. Specific conditions can be found, for example, in Journal of Heterocyclic Chemistry, 20(3), 623-8; 1983; Journal of Heterocyclic Chemistry, 45(5), 1451-1456. ; 2008); "Synthesis" (Synthesis, (18), 3027-3031; 2011).

(17) A compound of the formula (Ih) may be derived from a compound of the formula (XXXV) wherein L ³ , L ⁴ , L ⁶ and Q ' are as defined herein for a compound of formula (I) Compounds of formula (XIV) wherein R ² is C ₁ -C ₄ alkyl and Q, L ¹ , L ² and L ⁵ are as defined herein for the compound of formula (I). Such an addition reaction can be carried out in the presence of a base such as sodium hydride or sodium methoxide in a solvent such as tetrahydrofuran. Similar reactions are known and conditions can be found, for example, in "Organic & Biomolecular Chemistry" (2010), 8(12), 2777-2783) or "Journal of Scandinavian Chemistry" ( Acta Chemica Scandinavica, 53(4), 269-279; 1999).

(18) A compound of formula (XXXV) having from compound (wherein Q ', L ^3, L ⁴ and L ⁶ system as defined herein for compounds of formula (I), having the chemical formula (XXXVI) and R ²⁹ It is prepared by halogen, especially chlorine, bromine or iodine. Such transformations are well known. Examples and specific conditions can be found, for example, in Journal of Organic Chemistry, 70 (5), 1698-1703; 2005) or Tetrahedron (62 (42), 10005-10010; 2006). .

Well known to those skilled in the art, the reactions described in Schemes 1-4, 6-8, and 14-16 can also be accomplished using appropriate precursors of Q and Q and depending on possible side reactions, the precursors can be in any The stage is converted to Q or Q ' . Some examples of the preparation of such precursors and their conversion to Q are given in Schemes 9-16. It is clear to those skilled in the art that depending on possible side reactions, all of the reactions in Schemes 9-15 can also be performed simultaneously or sequentially to construct Q and Q ' .

(19) Alternatively, as seen in Scheme 9, a compound of formula (Im) wherein Q is Q-9 can be subjected to a condensation reaction to give a compound of formula (II) wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Q ' , X and R ¹² are as defined herein for the compound of formula (I) and T ¹ and T ² are C ₁ -C ₈ alkoxy groups, Or T ¹ and T ² together with the carbon to which they are attached form a carbonyl group or an acetal or ketal function in the form of C(OC ₁ -C ₆ -alkylene-O), whereby the alkylene The base fragment may optionally be mono-substituted to tetra-substituted with C ₁ -C ₆ alkyl) and reacted with a compound of formula (XVI) wherein R ¹³ is as defined herein for a compound of formula (I) To prepare. Typical reaction conditions for this type of reaction can be found in Journal of Organic Chemistry, 52 (22), 4978-84; 1987; Chemical & Pharmaceutical Bulletin, 51(2) , 138-151; 2003); Organic Letters, 10(2), 285-288; 2008); Journal of the American Chemical Society, 130(12), 4196-4201 ; 2008); Chemistry & Biology, 9(1), 113-129; 2002); Organic Preparations and Procedures International, 32(2), 153-159; 2000 ); "Scientia Pharmaceutica, 66 (1), 9-21; 1998); Journal of Medicinal Chemistry, 49 (17), 5177-5186; 2006); Agriculture and Food Chemistry Journal of Agricultural and Food Chemistry, 38(3), 839-44; 1990); Tetrahedron: Asymmetry, 8(2), 253-263; 1997); Journal of Pharmaceutical Chemistry (Journal of Medicinal Chemistry, 44 (21), 3339-3342; 2001); Bioorganic & Pharmaceutical Chemistry News (Bioorganic & Medicinal Chemistry Letters, 12(3), 341-344; 2002); US 2007032470; WO 07/058504; Journal of Organic Chemistry, 73(5), 2007-2010; 2008); Bioorganic & Medicinal Chemistry Letters, 19(10), 2683-2687; 2009); and Bioorganic & Medicinal Chemistry Letters, 19(10), 2654-2660; 2009).

(20) Alternatively, as seen in Scheme 9, a compound of formula (Im) may be obtained by reacting a compound of formula (Ik) which is a compound of formula (I) wherein R ¹³ is hydrogen A compound of the formula (XVII) wherein R ¹³ is as defined herein for a compound of formula (I) and R ²⁸ is a halogen (especially chlorine, bromine or iodine) or a sulfonate group, such as methylsulfonate It is prepared by reacting an acid ester, a tosylate, a triflate, a benzenesulfonate, a nitrobenzenesulfonate or a nonafluorobutylsulfonate.

Typical reaction conditions for alkylation in this manner can be found in Chinese Journal of Chemistry, 27(1), 33-42; 2009; WO 09/049846; Journal of Antibiotics Antibiotics, 61 (10), 603-614; 2008); Bioorganic & Medicinal Chemistry Letters, 18 (24), 6471-6475; 2008); Journal of Medicinal Chemistry, 51(15), 4601-4608; 2008); WO 06/123145; Pharmaceutical Literature (Weinheim, Germany) (Archiv der Pharmazie) (Weinheim, Germany), 340(4), 202-208; 2007); Synthetic Communications, 37(7), 1155-1165; 2007); Russian Journal of Organic Chemistry (Russian Journal of Organic Chemistry) , 42(5), 735-738; 2006); Bioinorganic Chemistry and Applications, 1 (3-4), 299-308; 2003); Synthetic Communications, 28 (Synthetic Communications) 14), 2621-2633; 1998); Synthetic Communications, 19 (18), 3129-38;

(21) The oxime of the formula (Ik) can be obtained by a condensation reaction, whereby a compound of the formula (II) is reacted with a hydroxylamine or alternatively with a salt of hydroxylamine. Typical conditions for such a reaction can be found in Journal of Heterocyclic Chemistry, 46(1), 116-118; 2009; Journal of Medicinal Chemistry, 20(5), 718 -21;1977); Journal of Organic Chemistry, 73(11), 4017-4026; 2008; EJEAFChe, Electronic Journal of Environmental, Agricultural and Food Chemistry, 5(5), 1515-1521; 2006); Advanced Synthesis & Catalysis, 346 (13-15), 1798-1811;

(22) Alternatively, as seen in Scheme 10, a compound of formula (I) may be obtained by formulating a compound of formula (III) wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Q ' , X is as defined herein for a compound of formula (I) and R ²⁹ is a halogen, especially chlorine, bromine or iodine) and a compound of formula (XVIII) wherein Q is as herein It is prepared by reacting a compound of the formula (I) and a M-based organometallic group. This can be accomplished using one of several techniques well known to those skilled in the art, including Suzuki, Stille, and Negishi cross-coupling reactions.

Examples and specific conditions for the Stirling reaction can be found in Bioorganic & Medicinal Chemistry Letters, 19 (19), 5689-5692; 2009; Journal of Organic Chemistry, 73(12), 4491-4495; 2008); Journal of the American Chemical Society, 129(3), 490-491; 2007 or Journal of Organic Chemistry, 75 (2), 424-433; 2010). Examples and specific conditions of the root-bank reaction can be found in the European Journal of Inorganic Chemistry (26), 4101-4110; 2008; Tetrahedron Letters, 50 (38), 5329- 5331; 2009); Tetrahedron Letters, 51 (2), 357-359; 2010) or Tetrahedron Letters, 51 (19), 2657-2659; 2010. Examples and specific conditions for Suzuki reaction can be found in Organic Letters (11(2), 345-347; 2009); Journal of the American Chemical Society, 131(20), 6961 -6963; 2009); Synthesis (Synthesis, (1), 85-90; 2010) or "Heterocycles, 80 (1), 359-368).

Process 11

(23) The compound of the formula (In) is a compound of the formula (I) wherein Q is Q-2, which may be derived from hydrazine having the formula (XIX) (wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Q ' and X are obtained as defined herein for the compound of formula (I). Such transformations can be accomplished using a number of conditions well known to those skilled in the art. Specific examples and conditions can be found in the Journal of European Chemistry (Chemistry-A European Journal, 16 (1), 89-94, S89/1-S89/10; 2010); "Tetrahedron Letters" (Tetrahedron Letters, 50 ( 49), 6818-6822; 2009); Bioorganic & Medicinal Chemistry Letters, 15(12), 2990-2993; 2005); Synthetic Communications, 27(14), 2521-2526; 1997); Journal of Combinatorial Chemistry, 7(4), 517-519; 2005) and Bioorganic & Medicinal Chemistry Letters, 15(12), 2990-2993; 2005).

(24) The hydrazine of the formula (XIX) may be derived from a nitrile having the formula (IV) (wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Q ' and X) are as defined herein for Prepared by the compound defined by (I). Typical conditions for such transformations can be found in Bioorganic & Medicinal Chemistry, 17(18), 6651-6658; 2009; Bioorganic & Medicinal Chemistry Letters, 19 (8), 2277-2281; 2009); Journal of Medicinal Chemistry, 51 (6), 1719-1729; 2008) or Journal of Medicinal Chemistry, 50 (26), 6535-6544; 2007).

(25) A nitrile having the formula (IV) can be produced from a compound of the formula (III) wherein R ²⁹ is a halogen, especially chlorine, bromine or iodine. Such transformations can be accomplished in a number of different conditions well known to those skilled in the art. Examples and specific conditions can be found in Journal of Organic Chemistry (2011), 76(2), 665-668; Journal of Medicinal Chemistry, 53(16), 6129-6152 ;2010); Organic Letters, 9 (9), 1711-1714; 2007); Journal of the American Chemical Society, 131 (3), 1305-1313; 2009); Synthesis (Synthesis, (20), 3351-3355; 2008) and "Chemistry-A European Journal" (13 (21), 6249-6254; 2007).

(26) A compound of the formula (Ip) is a compound of the formula (I) wherein the Q group Q-2 and Y ² and Y ³ together with the fragments to which they are attached form an aromatic carbocyclic ring (the carbocyclic ring) Optionally, one or more groups independently selected from the group consisting of halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, and C ₁ -C ₄ haloalkoxy a group substituted) and Y ⁴ is hydrogen or an alkyl group, which can utilize an oxidizing agent (such as 2,3-dichloro-5,6-dicyano group) in a different solvent such as dichloromethane, tetrahydrofuran, acetonitrile or toluene. - p -benzoquinone, oxygen, manganese (IV) oxide or ammonium cerium (IV) nitrate from a compound of formula (XX) via oxidation (wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ^6. Q ' and X are prepared as defined herein for the compound of formula (I). The reaction is usually carried out at a reaction temperature ranging from 0 ° C to the boiling point of the solvent or, alternatively, it can be carried out under microwave conditions.

(27) a compound of the formula (XX) wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Q ' and X are as defined herein for a compound of formula (I) and Y ² and Y ³ together with the fragments to which they are attached form an aromatic carbocyclic ring, which may optionally be independently selected from halo, C ₁ -C ₄ alkyl, C ₁ - The C ₄ haloalkyl group, the C ₁ -C ₄ alkoxy group, and the C ₁ -C ₄ haloalkoxy group are substituted, and the Y ⁴ -based hydrogen or alkyl group can be utilized in some techniques well known to those skilled in the art. One to prepare. For example, (XX) may be a compound of formula (IV) with a compound of formula (XXI) in the presence of thiourea or a metal alkoxide in a solvent such as an alcohol (where Y ² and Y ³ together) fragment on which they are attached to form an aromatic carbocyclic ring connected together, the carbocyclic ring may be optionally substituted with one or more groups independently selected from halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C _{The 1-} C ₄ alkoxy group and the C ₁ -C ₄ haloalkoxy group are substituted, and the Y ⁴ -based hydrogen or alkyl group is reacted to prepare. The reaction is usually carried out at a reaction temperature ranging from 0 ° C to the boiling point of the solvent or, alternatively, it can be carried out under microwave conditions.

(28) A compound of the formula (XXI) is a known compound, or can be easily obtained from a known compound by a procedure well known to those skilled in the art.

A specific example of such transformation is given in the experimental section herein.

(29) The compound of the formula (Iq) is a compound of the formula (I) wherein Q is Q-3 and Y ¹ is hydrogen, which can be derived from a compound of the formula (XXV) wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Q ' , X and Y ² are as defined herein for the compound of formula (I) and oxime of formula (XXVI) (wherein Y ⁴ is as herein) Obtained for the definition of the compound of formula (I). Typical conditions for such transformations can be found in Tetrahedron Letters, 50 (49), 6818-6822; 2009); Chemistry-A European Journal, 15(20), 5006-5011 ; 2009); Journal of Organic Chemistry (2009), 74 (12), 4646-4649) or Synthetic Newsletter (Synlett, (19), 3036-3040; 2008). The oxime family of formula (XXVI) is commercially available or can be prepared by methods well known to those skilled in the art.

(30) A compound of the formula (XXV) can be oxidized from a compound of the formula (XXIV) (wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Q ' , X and Y ² It is prepared as defined herein for the compound of formula (I). Such oxidation can be accomplished using a number of conditions well known to those skilled in the art. Specific reaction conditions can be found in the Journal of the American Chemical Society, 132 (8), 2532-2533; 2010; Journal of Organic Chemistry, 74 (15), 5750- 5753; 2009) or Tetrahedron (64 (29), 7008-7014; 2008).

(31) A compound of the formula (XXIV) may be derived from an aldehyde of the formula (XXII) wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Q ' and X are as defined herein for (Compound defined by the compound of (I)) is prepared with a compound of the formula (XXIII) wherein Y ² is as defined herein for the compound of formula (I). Typical conditions for such transformations can be found in Tetrahedron, 64 (29), 7008-7014; 2008); Journal of Organic Chemistry, 72 (20), 7783-7786; 2007) Or in Organic Letters (9(6), 1169-1171; 2007).

Process 14:

(32) A compound of the formula (Ir) wherein Q system Q-1 and Y ³ system H can be derived from a compound of the formula (XXIX) wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ^6. Q ' and X are prepared as defined herein for a compound of formula (I), Y ¹ is hydrogen or methyl, Y ⁴ is methyl or ethyl). Such transformations can be accomplished using a number of conditions well known to those skilled in the art.

(33) A compound of the formula (XXIX) can be as described in the Journal of European Chemistry (Chem. Eur. J. 2009, 15, 6811-6814) by using 1,2-dichloroethane. with trifluoromethanesulfonic acid trimethyl ester and Hu Ningshi silicon base (Hünig 's base) occurs at the reflux temperature of the reaction, the compound having the chemical formula (XXVIII) (where ^{L 1, L 2, L 3} , L 4, L ⁵ , L ⁶ , Q ' and X are prepared as defined herein for the compound of formula (I), Y ⁴ is methyl or ethyl and Y ¹ is hydrogen or methyl).

(34) A compound of the formula (XXVIII) may be derived from a compound of the formula (XXVII) wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Q ' and X are as defined herein for Prepared by the compound defined by (I). Such transformations can be accomplished using a number of conditions well known to those skilled in the art.

(35) The compound of the formula (Is) is a compound of the formula (I) wherein Q is Q-1, which may be a compound of the formula (XXX) (wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Q ' , X, Y ¹ , Y ² , Y ³ and Y ⁴ are prepared as defined herein for the compound of formula (I). Such transformations can be accomplished using a number of conditions well known to those skilled in the art. Specific examples and conditions can be found in the Journal of the Chemical Society, Perkin Transactions 1, (24), 3258-3264; 2001; Tetrahedron Letters, 46 (Tetrahedron Letters, 46) 14), 2361-2363; 2005); Synthesis (Synthesis, (10), 1664-1672; 2006) or Journal of Medicinal Chemistry, 53 (15), 5400-5421; 2010) .

(36) A dicarbonyl compound of formula (XXX) can be prepared by methods well known to those skilled in the art, including a compound of formula (XXXII) in the presence of a base (wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Q ' , X and Y ¹ are as defined herein for a compound of formula (I) and a compound of formula (XXXI) (Y ² , Y ³ and Y ⁴ are reacted as defined herein for the compound of formula (I). Specific examples and conditions for such transformation can be found in Journal of Medicinal Chemistry, 33(1), 52-60; 1990;; Chemistry-A European Journal, 13 (16) ), 4548-4559; 2007); Tetrahedron Letters, 46 (14), 2361-2363; 2005) and Journal of the Chemical Society, Perkin Transactions 1 , (24), 3258-3264; 2001).

(37) A compound of the formula (It) is a compound of the formula (I) wherein Q is the same as Q ' (Q and Q ' are represented as Q in Scheme 16), and L ¹ and L ⁴ are N, And D ⁵ is the same as D ⁶ (D ⁵ and D ⁶ are both represented as D ⁵ in Scheme 16), which can be derived from a compound of formula (XXXIX) (wherein X and D ⁵ are as herein The compound defined by I) is obtained with a hydrazine of the formula (XL) wherein the Q system is as defined herein for the compound of formula (I). Typical conditions for such transformations can be found in Synthesis (2003), (18), 2815-2826, Tetrahedron Letters, 50 (49), 6818-6822; 2009; "Chemistry-A European Journal" (15 20), 5006-5011; 2009); Journal of Organic Chemistry (2009), 74 (12), 4646-4649) or Chemical News (Synlett, (19), 3036-3040; 2008 )in. Lanthanides of formula (XL) are commercially available or can be prepared by methods well known to those skilled in the art.

(38) A compound of the formula (XXXIX) may be derived from a compound of the formula (XXXVIII) wherein R ²⁹ is a halogen, especially chlorine, bromine or iodine, and D ⁵ is as defined herein for a compound of formula (I) (Defined) is prepared with a compound of formula (XXXVII) wherein X is as defined herein for a compound of formula (I). Typical conditions for such transformations can be found in Synthesis (Synthesis (2003), (18), 2815-2826).

It has now been found that the compounds of formula (I) according to the invention have (for practical purposes) very advantageous activities for the protection of useful plants against diseases caused by phytopathogenic microorganisms (for example fungi, bacteria or viruses) Spectrum.

The invention therefore also relates to a method for controlling or preventing the infestation of a useful plant by a microorganism causing plant diseases, wherein a compound of formula (I) is applied as an active ingredient to a plant, a part thereof or a locus thereof. The compounds of formula (I) according to the invention are distinguished significantly by excellent activity, good plant tolerance and environmentally safe at low ratio applications. They have very useful therapeutic, prophylactic and systemic properties and are used to protect a wide variety of useful plants. Compounds of formula (I) can be used to inhibit or destroy diseases occurring on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of a variety of different useful plant crops, while also protecting, for example, Those plant parts that are grown from phytopathogenic microorganisms.

It is also possible to use compounds of the formula (I) as seed dressing agents for the treatment of plant propagation materials, in particular seeds (fruits, tubers, grains) and plant cuttings (for example rice) for protection. Fight against fungal infections along with fungi that cause phytopathogenic effects in the soil.

Furthermore, the compounds of formula (I) according to the invention can be used for controlling fungi in related fields, for example in the protection of industrial materials, including wood and wood-related industrial products, in food preservation or in hygiene management. .

Compounds of formula (I) are, for example, effective against the following classes of phytopathogenic fungi: deuteromycetes (eg, Botrytis, Trichosporon, Helminthosporium, Fusarium, Shell) Septoria, Cercospora and Alternaria, and Basidiomycetes (eg, Rhizoctonia, Hemileia, Puccinia). In addition, they also belong to the Ascomycetes (such as the genus of the genus Staphylococcus and Powdery Mildew, Podosphaera, Candida, H.) and Oomycetes (eg Phytophthora, Pythium) Genus, unilateral mold) is effective. Within the scope of the present invention, useful plants to be protected typically include the following plant species: cereals (wheat, barley, rye, oats, rice, corn, sorghum, and related species); beets (sugar radishes and beet); Pear fruit, stone fruit and soft fruits (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); legumes (beans, lentils, peas, soybeans); oil crops (canola, mustard, Poppy, olive, sunflower, coconut, castor oil plant, cocoa, groundnut); cucumber (squash, cucumber, melon); fiber plant (cotton, flax, hemp, jute); citrus fruit (orange, Lemon, grapefruit, citrus); vegetables (spinach, lettuce, asparagus, kale, carrot, onion, tomato, potato, red pepper); amaranth (avocado, cinnamon, camphor) or plants, such as tobacco, nuts , coffee, eggplant, sugar cane, tea, pepper, vine, hops, bananas and natural rubber plants, together with ornamental plants.

The term "useful plant" is understood to also include the imparting of a plurality of herbicides (like bromoxynil) or a plurality of classes of herbicides (eg, like HPPD inhibitors, ALS inhibitors, such as fluorine) due to conventional breeding methods or genetic engineering methods. Sulfasulfuron, flufensulfuron-methyl and triflusulfuron-methyl, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibition A useful plant for the tolerance of a agent, a GS (glutamate synthase) inhibitor or a PPO (pro-porphyrinogen oxidase) inhibitor. By conventional methods of breeding (mutagenesis) is given an example imidazolinones crops (such as imazamox) tolerance tie Clearfield ^® summer rape (canola (Canola)). Examples of crops that have been genetically engineered to be resistant to a wide variety of herbicide or herbicide classes include glyphosate resistant and glufosinate resistant varieties, which are available under the trade names RoundupReady ^® , Herculex I ^® and LibertyLink ^® . Commercially available.

The term "useful plant" is understood to also include useful plants which have been transformed by the use of recombinant DNA techniques to enable the synthesis of one or more selectively acting toxins, such as those known to be derived from toxin producing bacteria, especially spores. Those bacteria of the genus Bacillus. Examples of such plants are: YieldGard ^® (corn variety, expressing CryIA (b) toxin); YieldGard Rootworm ^® (corn variety, expressing CryIIIB (b1) toxin); YieldGard Plus ^® (corn variety, expressing CryIA (b) and CryIIIB (b1) toxin); Starlink ^® (corn variety, expressing Cry9(c) toxin); Herculex I ^® (corn variety, CryIF (a2) toxin and enzyme turf that achieves resistance to the herbicide glufosinate Phosphine N-acetyltransferase (PAT)); NuCOTN 33B ^® (cotton variety, expressing CryIA (c) toxin); Bollgard I ^® (cotton variety, expressing CryIA (c) toxin); Bollgard II® (cotton variety, expression) CryIA(c) and CryIIA(b) toxin); VIPCOT ^® (cotton variety, expressing VIP toxin); NewLeaf ^® (potato variety, expressing CryIIIA toxin); NatureGard ^® Agrisure ^® GT Advantage (GA21 glyphosate resistant), Agrisure ^® CB Advantage (Bt11 corn borer (CB) trait), Agrisure ^® RW (corn root trait) and Protecta ^® .

The term "useful plant" is understood to also include useful plants which have been transformed by the use of recombinant DNA techniques to enable the synthesis of selective anti-pathogenic substances, such as, for example, the so-called "pathogenesis-related proteins" (PRP). See, for example, EP-A-0 392 225). Some examples of such anti-pathogenic materials and transgenic plants capable of synthesizing such anti-pathogenic materials are known, for example, in EP-A-0 392 225, WO 95/33818 and EP-A-0 353 191. Such methods of producing such transgenic plants are generally known to those skilled in the art and are described, for example, above. In the publications mentioned.

As used herein, the term "location" of a useful plant is intended to encompass the place where the plant is grown, the place where the plant propagation material of the useful plant is sown, or the soil into which the propagation material of the useful plant will be placed. An example of such a site is a field on which crop plants are grown.

The term "plant propagation material" is understood to mean the reproductive part of a plant, such as seeds, which parts can be used for the propagation of the latter, as well as plant-based materials such as cuttings or tubers (for example potatoes). Mention may be made, for example, of seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants. Germinated plants and young plants transplanted after germination or after germination from the soil may also be mentioned. These young plants can be protected by full or partial treatment by dipping prior to transplantation. Preferably, "plant propagation material" is understood to mean a seed.

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

The invention therefore also relates to compositions for the control and protection of phytopathogenic microorganisms, the compositions comprising a compound of formula (I) and an inert carrier, and to methods for controlling or preventing the infestation of useful plants by phytopathogenic microorganisms And a composition comprising a compound of formula (I) as an active ingredient and an inert carrier, applied to the plant, a part thereof or a locus thereof.

In this regard, the compound of formula (I) and the inert carrier are conveniently formulated in a known manner as emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, diluted emulsions, wettable powders , soluble powders, dust, granules, and also encapsulants (eg, in polymeric materials). For this type of composition, methods of application, such as spraying, atomization, Powdering, scattering, coating or pouring can be selected according to the intended purpose and the dominant environment. The compositions may also contain other adjuvants such as stabilizers, antifoaming agents, viscosity modifiers, binders or tackifiers along with fertilizers, micronutrient donors or other formulations for obtaining particular effects.

Suitable carriers and adjuvants (auxiliaries) may be solid or liquid, and are useful in formulation techniques, such as natural or regenerated minerals, solvents, dispersants, wetting agents, tackifiers, thickeners, Adhesive or fertilizer. Such a carrier is described, for example, in WO 97/33890.

The compound of the formula (I) or a composition comprising the compound of the formula (I) as an active ingredient and an inert carrier can be applied to the plant locus or plant to be treated (simultaneously or sequentially with other compounds). These other compounds may be, for example, fertilizers or micronutrient donors or other products that affect plant growth. They may also be selective herbicides, together with insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired in the formulation field. The carrier, surfactant or adjuvant to facilitate administration.

Preferred methods for administering a compound of formula (I) or a composition comprising a compound of formula (I) as an active ingredient together with an inert carrier are applied topically. The frequency of administration and rate of application will depend on the risk of infection by the corresponding pathogen. However, the compound of formula (I) can also be applied to the soil by a liquid formulation or by applying the compound in solid form to the soil, for example in the form of granules (soil application) by roots via the soil (Systemic action) penetrates the plant. In rice crops, such granules can be applied to water-immersed rice fields. Compounds of formula (I) can also be formulated by liquids using fungicides The seeds are impregnated with seeds or tubers or coated with a solid formulation and applied to the seeds (coating).

Formulations are prepared in a known manner (i.e., containing a composition of a compound of formula (I) and, if desired, a solid or liquid adjuvant), typically by using the compound with a extender, such as a solvent, a solid carrier, and Optionally, the surface active compound (surfactant) is intimately mixed and/or milled.

The agrochemical formulations generally comprise from 0.1% to 99% by weight, preferably from 0.1% to 95% by weight of the compound of formula (I), from 99.9% to 1% by weight, Preferred are 99.8% to 5% by weight solid or liquid adjuvant and from 0 to 25% by weight, preferably from 0.1% to 25% by weight of surfactant.

Although it is preferred to formulate commercial products as concentrates, the end user typically uses a diluted formulation.

Advantageous application rates are generally from 5 g to 2 kg of active ingredient (ai) per hectare (ha), preferably from 10 g to 1 kg ai/ha, most preferably from 20 g to 600 g ai/ Ha. When used as a seed wetting agent, a convenient application rate is from 10 mg to 1 g of active substance per kg of seed. The rate of application for the desired effect can be determined experimentally. It depends, for example, on the type of action, the stage of development of the useful plant, and the application (location, timing, method of administration), and may vary within wide limits due to such parameters.

The compound of formula (I) or a pharmaceutical salt thereof as described above may also have an advantageous spectrum of activity for the treatment and/or prevention of microbial infestation in an animal. The "animal" may be any animal, such as an insect, a mammal, a reptile, a fish, an amphibian, preferably a mammal, and most preferably a human. "Treatment" means use on animals with microbial infestation To reduce or slow or stop the increase or spread of the infection, or to reduce the infection or treat the infection. "Prophylaxis" means using an animal that has no visible signs of microbial infestation to prevent any future infestation, or to reduce or slow the increase or spread of any future infection.

According to the present invention, there is provided the use of a compound of formula (I) for the manufacture of a medicament for the treatment and/or prevention of microbial infestation in an animal. Also provided is the use of a compound of formula (I) as a pharmaceutical agent. Also provided is the use of a compound of formula (I) as an antimicrobial agent in the treatment of animals. According to the present invention, there is also provided a pharmaceutical composition comprising, as an active ingredient, a compound of formula (I), or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable diluent or carrier. The composition can be used to treat and/or prevent antimicrobial infestation in an animal. The pharmaceutical composition may be in a form suitable for oral administration such as tablets, troches, hard capsules, aqueous suspensions, oily suspensions, emulsions, dispersible powders, dispersible granules, syrups and elixirs Agent. Alternatively, the pharmaceutical composition may be in a form suitable for topical administration, such as a spray, a cream or a lotion. Alternatively, the pharmaceutical composition may be in a form suitable for parenteral administration (e.g., injection). Alternatively, the pharmaceutical composition may be in an inhalable form, such as a spray.

Compounds of formula (I) are effective against a wide variety of microbial species that are capable of causing microbial infestation in animals. Examples of such microbial species are those causing aspergillosis, such as Aspergillus fumigatus, Aspergillus fumigatus, Aspergillus terreus, Aspergillus nidulans and Aspergillus niger , those causing blastomycosis, such as dermatitis buds ; those causing candidiasis, For example , Candida albicans, Candida glabrata, Candida tropicalis, Candida parapsilosis, Candida krusei, and Candida albicans ; those that cause coccidioidomycosis, such as Coccidioides ; those that cause cryptococcosis, such as newborns Cryptococcus ; those causing histoplasmosis, such as capsular histoplasma ; and those causing zygomycetes, such as P. aureus , Rhizomucor pneumoniae and Rhizopus rhizogenes . Further examples are Fusarium, such as Fusarium oxysporum and Fusarium solani , and genus A. faecalis, such as S. cerevisiae and Polysporosis . Still other examples are Microsporospores, Trichophyton, Epidermidis, Mucor, Sporotrichum, Candida, Mycoplasma, Mycoplasma, Paraspora and Histoplasma genus.

The compositions of the present invention may comprise other biologically active compounds, such as micronutrients, or compounds having fungicidal activity, or compounds having activity to modulate plant growth, weeding, insecticidal, nematicidal or acaricidal activity.

The present invention provides a fungicidal composition comprising a fungicidally effective amount of a compound of formula (I), optionally including additional active ingredients. The compound of formula (I) may be the sole active ingredient of the composition or, where appropriate, it may be combined with one or more additional active ingredients (for example insecticides, fungicides, synergists, herbicides or plants) Conditioner) mixed. Such additional biocidal active ingredients are known, for example, from "The Pesticide Manual" [The Pesticide Manual - A World Compendium; Edition (new edition (November 2, 2003)); editor: CDSTomlin (Tomlin); The British Crop Protection Council, ISBN-10: 1901396134; ISBN-13: 978-1901396133] or Its electronic version of the "e-Pesticide Manual V4.2", or from the website http://www.alanwood.net/pesticides/, or preferably one of the additional pesticides listed below .

The following mixture of the compound of TX and the other active ingredient (B) is preferred (the abbreviation "TX" means a compound included in the compound of formula I, or preferably, the term "TX" means selected from Table 2. Compound): (B) (B1) strobilurin fungicide + TX, (B2) azole fungicide + TX, (B3) The fungicide +TX, (B4) anilinopyrimidine fungicide + TX (B5) is selected from the group consisting of fungicides, the group consists of the following: fluconazole + TX, cis-fluconazole +TX, Fluxapyroxad + TX, imipenem + TX, flurazia + TX, isothiazide + TX, downy mildew + TX, carbendazim + TX, herbicide smoke + TX, benzathine + TX, benzophenone + TX, o-iodoaniline + TX, benomyl + TX, phenothiamine + TX, phenothiamine + TX, biphenyl + TX, biphenyl Triadimefol + TX, quercetin + TX, Bordeaux mixture + TX, pyridine pyridinium + TX, sulfonic acid butyl pyrimidine + TX, cadmium chloride + TX, captan + TX, captan + TX, more Bacterium + TX, carbon disulfide + TX, rust rust + TX, ciprofloxacin + TX, cedar leaf oil + TX, cockroach + TX, chlorine + TX, Di Mao powder + TX, chlorothalonil + TX , ethyl bacteriophage + TX, cinnamaldehyde + TX, copper + TX, copper ammonium carbonate + TX, copper hydroxide + TX, copper octoate + TX, copper oleate + TX, copper sulfate + TX, cyanosin + TX, Cycloheximide + TX, cymoxanil + TX, phenylfluorosulfonamide + TX, dichloronaphthylquinone + TX, dichloropropene + TX, chloramphenicol + TX, sputum clear + TX, chloramine + TX , carbendazim + TX, difluoroline + TX, dipyrimidine Phenol + TX, ene morpholine + TX, dipyridamole + TX, dithianon + TX, polydextrene + TX, gram sputum + TX, ethaboxam + TX, acetazol + TX, carbendazim +TX, famoxadone + TX, imidacloprid + TX, dipyridamole + TX, benzene phosphate + TX, chloropyrimidin + TX, metofuranilide + TX, cyclosporin + TX, cyanide Phytosamine + TX, seed dressing + TX, triphenyltin acetate + TX, triphenyltin chloride + TX, toxic tin + TX, thiram + TX, azoxystrobin + TX, fluazinam + TX, fluoride Malignant bacteria + TX, sulforaphane + TX, sulfamethoxazole + TX, flubenamide + TX, sterilized Dan + TX, formaldehyde + TX, aluminum triethyl phosphate + TX, tetrachlorobenzoquinone + TX, wheat spike + TX, furosemide + TX, Folabi + TX, flyodin + TX, bisazinine + TX, hexachlorobenzene + TX, carbendazim + TX, bis-octylamine + TX, 3-iodo-2 - propiylbutyl carbamate (iodocarb) + TX, isoindazin + TX, iprodione + TX, propidium zinc + TX, rice bran + TX, chunleimycin + TX, dysen Manganese-zinc+TX, manco-manganese+TX, manganese dimethyldithiocarbamate+TX, refined metalaxyl+TX, rust-free amine+TX, mercuric chloride+TX, mercury+TX, metalaxyl +TX, sulfavir+TX, Daisenlian+TX, benomyl+TX, dexamethasone+TX, India Tree oil (hydrophobic extract) + TX, fluoropyrimidin + TX, octyl isothiophenone + TX, mesofuramide + TX, vesculine + TX, quinoline copper + TX, ox quinic acid + TX, Oxidized rust rust + TX, oxytetracycline + TX, paclobutrazol + TX, paraffin oil + TX, paraformaldehyde + TX, pentosan + TX, pentachloronitrobenzene + TX, pentachlorophenol + TX, pyridine Insectamine + TX, rice oxime ester + TX, phosphoric acid + TX, polyoxomycin + TX, polyoxomycin D zinc salt + TX, potassium bicarbonate + TX, thiabendazole + TX, procymidone + TX, Rolly mildew + TX, propidium zinc + TX, propoxyquinoline + TX, adiprocarb + TX, fixed phosphorus + TX, pyridine quinone + TX, praziquantel + TX, quinoxaline + TX, five Chloronitrobenzene + TX, thiazide + TX, sodium bicarbonate + TX, sodium diacetate + TX, sodium propionate + TX, streptomycin + TX, sulfur + TX, TCMTB + TX, leaf withered + TX, tetrachloronitrobenzene + TX, thiabendazole + TX, thiufamide + TX, thiophanate + TX, thiophanate + TX, thiram + TX, methyl phos +TX, toluene sulfonamide + TX, zodiazepine + TX, Trichoderma harzian + TX, tricyclazole + TX, oxazinamide + TX, triphenyltin hydroxide + TX, jinggangmycin + TX, olefin Ketone + TX, Daisen zinc + TX, zinc dimethyl dithiocarbamate + TX, Benzoylamide + TX, 1+TX, 1-bis(4-chlorophenyl)-2-ethoxyethanol + TX, 2+TX, 4-dichlorophenyl benzenesulfonate + TX, 2-fluoro - N -methyl- N -1-naphthylamine + TX, 4-chlorodiphenyl hydrazine + TX, compound of formula B-5.1 + TX Compound with chemical formula B-5.2+TX Compound with chemical formula B-5.3 + TX Compound with chemical formula B-5.4+TX Compound with chemical formula B-5.5+TX Compound with chemical formula B-5.6 + TX Compound with chemical formula B-5.7+TX 3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (2-dicyclopropyl-2-yl-phenyl)-decylamine (Compound B-5.8) + TX, 3-di Fluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-isopropyl-1,2,3,4-tetrahydro-1,4-methyl bridge-naphthalen-5-yl)-oxime Amine (Compound B-5.9) + TX, 1,3-Dimethyl-5-fluoro-1H-pyrazole-4-carboxylic acid [2-(1,3-dimethylbutyl)phenyl]-decylamine (Compound B-5.10) + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4'-dichloro-5-fluoro-1,1'-biphenyl Benzyl-2-yl)-nonylamine (Compound B-5.11) + TX, N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(three Fluoromethyl)benzamide (Compound B-5.12)+TX, 3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid N-[2-(1,1,2,2 -tetrafluoroethoxy)phenyl]-nonylamine (Compound B-5.13) + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid N-[2-(1, 1,2,3,3,3-hexafluoropropoxy)phenyl]-nonylamine (Compound B-5.14), 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid N -[2-(2-chloro-1+TX, 1,2-trifluoroethoxy)phenyl]-nonylamine (Compound B-5.15) + TX, 3-difluoromethyl-1-methyl- 1H-pyrazole-4-carboxylic acid N-(4'-trifluoromethyl-biphenyl-2-yl)-decylamine (Compound B-5.16) + TX, 3-difluoromethyl-1-methyl- 1H- Pyrazole-4-carboxylic acid N-(2'-trifluoromethyl-biphenyl-2-yl)-decylamine (Compound B-5.17) + TX, 3-difluoromethyl-1-methyl-1H- Pyrazole-4-carboxylic acid N-(2'-trifluoromethyl-biphenyl-2-yl)-decylamine (Compound B-5.18) + TX, 3-difluoromethyl-1-methyl-1H- Pyrazole-4-carboxylic acid (4'-methylsulfanyl-biphenyl-2-yl)-decylamine (Compound B-5.19) + TX, 3-difluoromethyl-1-methyl- 1H-pyrazole-4-carboxylic acid (2-dichloromethylene-3-ethyl-1-methyl-dihydroindol-4-yl)-decylamine (Compound B-5.20)+TX has the chemical formula B- 5.21 compound + TX (B6) a plant biological regulator selected from the group consisting of activated ester (Acibenzolar) + TX, 1-methyl-cyclopropene + TX, activated ester-S-methyl + TX, short Zhuangsu + TX, ethephon + TX, ketamine and anti-peptidyl ester; (B7) selected from the group consisting of insecticides, the group consists of: abametine + TX, clothianidin + TX ,inhibited-benzoate+TX, indoleamine+TX, tefluthrin+TX, thiamethoxam+TX, and compound C with chemical formula C+TX

Wherein X is a divalent group selected from the group consisting of as well as Wherein a) R ₁ is a cyclopropyl group substituted with a cyclopropyl group at the 1-position, R ₂ is a bromine group, R ₃ is a methyl group, R ₄ is a CN and X is X ₁ ; b) R ₁ is substituted by a cyclopropyl group. Methyl, R ₂ is CF ₃ , R ₃ is methyl, R ₄ is Cl and X is X ₁ ; c) R ₁ is cyclopropyl substituted at the 1-position with a cyclopropyl group, R ₂ is CF ₃ , R ₃ is methyl, R ₄ is Cl and X is X ₁ ; d) R ₁ is cyclopropyl substituted with a cyclopropyl group at the 1-position, R ₂ is a CF ₃ , R ₃ is a methyl group, and R ₄ is a CN. And X system X ₁ ; e) R ₁ is a cyclopropyl group substituted with a cyclopropyl group at the 1-position, R ₂ is OCH ₂ CF ₃ , R ₃ is a methyl group, R ₄ is a CN and X is X ₁ ; f) R ₁ is isopropyl, R ₂ is methoxy; R ₃ is methyl; R ₄ is hydrogen and X is X ₈ ; g) R ₁ is isopropyl, R ₂ is trifluoromethyl; R ₃ is Chlorine, R ₄ is hydrogen and X is X ₈ ; h) R ₁ is isopropyl, R ₂ is trifluoromethyl; R ₃ is methyl, R ₄ is hydrogen and X is X ₈ ; i) R ₁ is Methyl, R ₂ is bromine; R ₃ is methyl; R ₄ is CN and X is X ₁ ; j) R ₁ is methyl, R ₂ is bromine; R ₃ is methyl, R ₄ is Cl and X is X _1; and (B8) glyphosate + TX, diammonium glyphosate + TX, dimethyl ammonium glyphosate + TX, isopropyl ammonium glyphosate + TX, glyphosate Ammonium + TX, glyphosate potassium + TX, glyphosate sesquioxide + TX, glyphosate trimethyl sulphide + TX, (5-chloro-2,4-dimethyl-pyridin-3-yl)- (2,3,4-Trimethoxy-6-methyl-phenyl)-methanone + TX, (5-bromo-4-chloro-2-methoxy-pyridin-3-yl)-(2, 3,4-Trimethoxy-6-methyl-phenyl)-methanone + TX, 2-{2-[(E)-3-(2,6-dichloro-phenyl)-1-methyl -prop-2-ene-(E)-ylideneaminooxymethyl]-phenyl}-2-[(Z)-methoxyimino]-N-methyl-acetamide + TX, 3-[5-(4-chloro-phenyl)-2,3-dimethyl-iso Zolidine-3-yl]-pyridine + TX compound of formula D + TX Floxacin + TX, glufosinate and its salt + TX, and (B9) Isopyrazam + TX, Sedaxane + TX, compound of formula (E) + TX Compound of formula (F) + TX A plurality of preferred compositions, including a compound of formula TX and (B) a compound selected from the group consisting of: (B1) spore coccitor fungicide + TX, (B2) azole Fungicide +TX, (B3) Morpho fungicide + TX, (B4) anilinopyrimidine fungicide + TX, (B5) selected from the group consisting of fungicides, the group consists of: carbendazim (878) + TX, arsenic acid Salt + TX, benzathine (56) + TX, benzophenone + TX, o-iodoaniline (896) + TX, benomyl (62) + TX, phenothiamine + TX, phenothiamine -isopropyl (68) + TX, biphenyl (81) + TX, biphenyl triazole alcohol (84) + TX, blasticidin-S (85) + TX, Bordeaux mixture (87) + TX , pyridine azide (88) + TX, acetaminophen sulfonate (98) + TX, cadmium chloride + TX, captan (113) + TX, captan (114) + TX, carbendazim (116)+TX, carbon disulfide (945)+TX, rust rust (120)+TX, ciprofloxacin (122)+TX, cedar leaf oil+TX, cockroach (126)+TX, chloro+ TX, Di Mao San (139) + TX, chlorothalonil (142) + TX, ethyl bacillus (149) + TX, cinnamaldehyde + TX, copper + TX, copper ammonium carbonate + TX, copper hydroxide (169) +TX, copper citrate (170) + TX, copper oleate + TX, copper sulfate (87) + TX, cyanosin (185) + TX, cycloheximide (1022) + TX, cymoxanil (200) +TX, phenylfluorosulfonamide (230)+TX, dichloronaphthylquinone (1052)+TX, dichloropropene (233)+TX, dicyandiamide (237)+TX, chymone (239)+TX Dichloronitro Amine (240)+TX, carbendazim (245)+TX, difluoroline (253)+TX, bispronol (1082)+TX, olefin morpholine (263)+TX, enemies (270 ) +TX, dithianon (279) + TX, polyguoding (289) + TX, gram (290) + TX, ethaboxam (304) + TX, acetazol (1133) + TX, soil Fungic (321) + TX, famoxadone (322) + TX, imidacloprid (325) + TX, sodium sulfonate (1144) + TX, benzene phosphorus (326) + TX, chloropyrimidinol ( 327) +TX, toluidine aniline (333) + TX, cyclosporin (334) + TX, cyanamide (338) + TX, seed dressing (341) + TX, triphenyltin acetate (347 ) +TX, triphenyltin chloride + TX, toxic tin (347) + TX, thiram (350) + TX, azoxystrobin (351) + TX, fluazinam (363) + TX, fluorobacteria ( 368) +TX, sulforamidamide (394) + TX, fluridamide (396) + TX, sterilized Dan (400) + TX, formaldehyde (404) + TX, aluminum triethyl citrate (407) + TX, tetrachloro Benzoquinone (643)+TX, Maishenning (419)+TX, furosemide (410)+TX, Furabi (411)+TX, flyodin(1205)+TX, bisazinine (422) ) +TX, hexachlorobenzene (434) + TX, carbendazim + TX, bis-octylamine (459) + TX, iodocarb (3-iodo-2-propynyl butyl urethane) + TX, Iridium (IBP) (469) + TX, Iprodiurea (470) + TX, Bingsen Zinc (471)+TX, Indigo (474)+TX, Chunleimycin (483)+TX, Mancozeb (496)+TX, Mancozeb (497)+TX, dimethyldithio Manganese carbazide + TX, refined metalaxyl (metalaxyl-M) (517) + TX, rust-eliminating amine (510) + TX, mercuric chloride (511) + TX, mercury + TX, metalaxyl ( 516) +TX, sulfavir (528) + TX, Daisenlian (546) + TX, benomyl + TX, dexamethasone (566) + TX, neem oil (hydrophobic extract) + TX, Fluoropyrimidin (587) + TX, octyl isothiophenone (590) + TX, mezylamine (592) + TX, vesculine (601) + TX, quinoline copper (605) + TX, Austria Solicylic acid (606)+TX, oxidized rust (608)+TX, oxytetracycline (611)+TX, paclobutrazol (612)+TX, paraffin oil (628)+TX, paraformaldehyde+TX, pentane Bacterium (620) + TX, pentachloronitrobenzene (716) + TX, pentachlorophenol (623) + TX, penthiopyran + TX, rice decyl ester + TX, phosphoric acid + TX, polyoxymycin ( 654)+TX, polyoxomycin D zinc salt (654)+TX, potassium bicarbonate+TX, thiabendazole (658)+TX, procymidone (660)+TX, propamocarb (668)+TX , Bensen zinc (676) + TX, propoxyquinoline (682) + TX, amine propyl (1361) + TX, fixed phosphorus (693) + TX, guanidinium (703) + TX, praziquantel (710)+TX, quinoxaline (715)+TX, pentachloronitrobenzene (PCNB)(716)+TX, thiabendamide (729)+TX, sodium bicarbonate+TX, sodium diacetate+TX, sodium propionate+TX, streptomycin (744)+TX, sulfur (754) +TX, TCMTB+TX, leaf sputum + TX, tetrachloronitrobenzene (TCNB) (767) + TX, thiabendazole (790) + TX, cefotaxime (796) + TX, thiophanate (1435) + TX, thiophanate-methyl (802) + TX, thiram (804) + TX, methyl phosphatidyl (808) + TX, toluene sulfonamide (810) + TX, zocilazine (821 ) +TX, Trichoderma harzianum (825) + TX, tricyclazole (828) + TX, oxazinamide (838) + TX, triphenyltin hydroxide (347) + TX, Jinggangmycin (846) + TX, ketene (849) + TX, zinc (855) + TX, zinc dimethyl dithiocarbamate (856) + TX, benzoic acid (857) + TX, 1, 1- Di(4-chlorophenyl)-2-ethoxyethanol (IUPAC-name) (910)+TX, 2+TX, diphenyl phenyl 4-benzenesulfonate (IUPAC-/Chemical Abstracts-Name) (1059 +TX, 2-fluoro- N -methyl- N- 1-naphthylacetamide (IUPAC-name) (1295) + TX, 4-chlorophenylphenyl hydrazine (IUPAC-name) (981) + TX , compound with chemical formula B-5.1 + TX Compound with chemical formula B-5.2+TX Compound with chemical formula B-5.3 + TX Compound with chemical formula B-5.4+TX Compound with chemical formula B-5.5+TX Compound with chemical formula B-5.6 + TX Compound with chemical formula B-5.7+TX 3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (2-dicyclopropyl-2-yl-phenyl)-decylamine (Compound B-5.8) + TX, 3-di Fluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-isopropyl-1,2,3,4-tetrahydro-1,4-methyl bridge-naphthalen-5-yl)-oxime Amine (Compound B-5.9) + TX, 1,3-Dimethyl-5-fluoro-1H-pyrazole-4-carboxylic acid [2-(1,3-dimethylbutyl)phenyl]-decylamine (Compound B-5.10) + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4'-dichloro-5-fluoro-1,1'-biphenyl Benzyl-2-yl)-nonylamine (Compound B-5.11) + TX, N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(three Fluoromethyl)benzamide (Compound B-5.12)+TX, 3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid N-[2-(1,1,2,2 -tetrafluoroethoxy)phenyl]-nonylamine (Compound B-5.13) + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid N-[2-(1, 1,2,3,3,3-hexafluoropropoxy)phenyl]-nonylamine (Compound B-5.14) + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4- N-[2-(2-chloro-1,1,2-trifluoroethoxy)phenyl]-decylamine (Compound B-5.15) + TX, 3-difluoromethyl-1-methyl- 1H-pyrazole-4-carboxylic acid N-(4'-trifluoromethyl-biphenyl-2-yl)-decylamine (Compound B-5.16) + TX, 3-difluoromethyl-1-methyl- 1H- N-(2'-trifluoromethyl-biphenyl-2-yl)-decylamine (Compound B-5.17) + TX and 3-difluoromethyl-1-methyl-1H-pyrazole Oxazole-4-carboxylic acid N-(2'-trifluoromethyl-biphenyl-2-yl)-decylamine (Compound B-5.18) + TX (B6) is selected from the group consisting of plant biological regulators, the group consisting of The following components are: arsenic acid benzene-S-methyl (6) + TX, chlormequat (137) + TX, ethephon (307) + TX, meperidine (509) and trinexarate ( 841); (B7) an insecticide selected from the group consisting of abamectin (1) + TX, clothianidin (165) + TX, indomethacin - benzoate (291)+TX, indoleamine (458)+TX, tefluthrin (769)+TX, thiamethoxam (792)+TX, compound of formula B-7.1+TX And a compound of formula B-7.2 + TX; And (B8) glyphosate (419) + TX.

Examples of particularly suitable mixtures selected from the group P below: Group P: particularly suitable mixtures according to the invention: sporangin fungicides selected from the group consisting of azoxystrobin (47) + TX, ether Bismuth (226)+TX, fluoxastrobin (382)+TX, oxystrobin (485)+TX, phenoxystrobin (551)+TX, acesulfame+TX, oxypoxystrobin (647) +TX, pyraclostrobin (690); trifloxystrobin (832) + TX, compound with chemical formula B-1.1 + TX An azole fungicide selected from the group consisting of aziconazole (40) + TX, carbendazole (96) + TX, cyproconazole (207) + TX, difenoconazole (247) + TX, Oxazol (267) + TX, diniconazole M (267) + TX, oxaconazole (298) + TX, nitrile azole (329) + TX, flurazol (385) + TX, flucarbazole ( 393) +TX, fluconazole (397) + TX, hexaconazole (435) + TX, imazalil (449) + TX, hydrazol (457) + TX, inophanazole (468) + TX, leaves Pyrazole (525) + TX, myclobutanil (564) + TX, mzoimidazole (607) + TX, rice decyl ester (618) + TX, penconazole (619) + TX, prochloraz (659) + TX, propiconazole (675) + TX, prothioconazole (685) + TX, flurazol (731) + TX, tebuconazole (761) + TX, fluoroetherazole (778) + TX, triazole Ketone (814) + TX, triazolol (815) + TX, fluconazole (834) + TX, sterilized azole (842) + TX, benzyl chlorotriazol (1068) + TX, ethiazole (1129) +TX, furazolidone (1198) + TX, furose oxazole (1199) and quinconazole (1378); selected from the following Porphyrin fungicidal mixture: 4-dodecyl-2,6-dimethyl Porphyrin+TX, cycloalkanoline (288)+TX, butylmorpholine (344)+TX, tridemorpholine (830)+TX, fenpropidin (343)+TX, spirocyclam (740) +TX, powder disease (648) and compound with chemical formula B-3.1 + TX An anilinopyrimidine fungicide selected from the group consisting of cyprodinil (208) + TX, azoxystrobin (508) and pyrimethanil (705); a mixture of fungicides selected from the group consisting of The following components: carbendazim (878) + TX, arsenate + TX, benzathine (56) + TX, benzophenone + TX, o-iodoaniline (896) + TX, benomyl ( 62) +TX, phenothiamine + TX, phenothiamine-isopropyl (68) + TX, biphenyl (81) + TX, biphenyl triazole alcohol (84) + TX, blasticidin -S(85)+TX, Bordeaux mixture (87)+TX, acetamiprid (88)+TX, acetaminophen sulfonate (98)+TX, cadmium chloride+TX, captan (113 ) +TX, captan (114) + TX, carbendazim (116) + TX, carbon disulfide (945) + TX, rust (120) + TX, ciprofloxacin (122) + TX, snow Pine leaf oil + TX, cockroach cockroach (126) + TX, chlorine + TX, Di Mao San (139) + TX, chlorothalonil (142) + TX, ethyl bacillus (149) + TX, cinnamaldehyde + TX, Copper + TX, copper ammonium carbonate + TX, copper hydroxide (169) + TX, copper octoate (170) + TX, copper oleate + TX, copper sulfate (87) + TX, cyanosin (185) + TX, Cycloheximide (1022)+TX, cymoxanil (200)+TX, phenylfluorosulfonamide (230)+TX, dichloronaphthylquinone (1052)+TX, dichloropropene (233)+TX, dichloro Cyanamide (237)+TX, chlorfenapyr (239)+TX, dichloronitroaniline (240)+TX, carbendazim (245)+TX, difluronium (253)+TX, dipyrimidine Phenol (1082)+TX, olefin morpholine (263)+TX, carbendazole (270)+TX, dithianon (279)+TX, multi-fruit (289)+TX, gram 瘟(290) +TX, ethaboxam (304) + TX, acetem (1133) + TX, carbendazim (321) + TX, famoxadone (322) + TX, idacene (325) + TX, enemy Sodium sulfonate (1144)+TX, phenylphosphine (326)+TX, chloropyrimidinol (327)+TX, mezyl anilide (333)+TX, cycloheximide (334)+TX, cyanamide (338)+TX, seed dressing (341)+TX, triphenyltin acetate (347)+TX, triphenyltin chloride+TX, toxic tin (347)+TX, thiram (350)+TX, Azoxystrobin (351) + TX, fluazinam (363) + TX, fluorobacteria (368) + TX, sulforamidamide (394) + TX, flubenzamide (396) + TX, sterilized Dan (400) +TX, Formaldehyde (404)+TX, Aluminum Triethyl Phosphate (407)+TX, Tetrachlorobenzoquinone (643)+TX, Maisuining (419)+TX, Furosemide (410)+TX, Fula Ratio (411)+TX, flyodin(1205)+TX, fuazatine (422)+TX, hexachlorobenzene (434)+TX, carbendazim+TX, bis-octylamine (459)+TX, Iodocarb(3-iodo-2-propynylbutylcarbamate)+TX Isophagous (IBP) (469)+TX, iprodione (470)+TX, propidium zinc (471)+TX, indole (474)+TX, chunleimycin (483)+TX, generation Manganese zinc (496)+TX, mancozeb (497)+TX, manganese dimethyldithiocarbamate+TX, refined metalaxyl (metalaxyl-M) (517)+TX, rust-free Amine (510)+TX, mercuric chloride (511)+TX, mercury+TX, metalaxyl (516)+TX, sulfavir (528)+TX, desensen (546)+TX, benomyl +TX, dexamethasone (566) + TX, neem oil (hydrophobic extract) + TX, fluoropyrimidinol (587) + TX, octyl thialinone (590) + TX, metofuramide ( 592)+TX, oxalin (601)+TX, quinoline copper (605)+TX, oxolinic acid (606)+TX, oxidized rust (608)+TX, oxytetracycline (611)+ TX, paclobutrazol (612) + TX, paraffin oil (628) + TX, paraformaldehyde + TX, pentosan (620) + TX, pentachloronitrobenzene (716) + TX, pentachlorophenol (623) + TX, penthiopyrene + TX, rice decyl ester + TX, phosphoric acid + TX, polyoxymycin (654) + TX, polyoxomycin D zinc salt (654) + TX, potassium bicarbonate + TX, thiabium Ling (658)+TX, procymidone (660)+TX, propamocarb (668)+TX, propidium zinc (676)+TX, propoxyquinoline (682)+TX, adipro (1361) +TX, fixed bacteria phosphorus (693) + TX, pyridine plaque (703) + TX, Roquequinone (710) + TX, quinoxaline (715) + TX, pentachloronitrobenzene (PCNB) (716) + TX, thiosporin (729) + TX, sodium bicarbonate + TX, diacetic acid Sodium + TX, sodium propionate + TX, streptomycin (744) + TX, sulfur (754) + TX, TCMTB + TX, leaf cumin + TX, tetrachloronitrobenzene (TCNB) (767) + TX, Thiabendazole (790) + TX, thiufamide (796) + TX, thiophanate (1435) + TX, thiophanate-methyl (802) + TX, thiram (804) + TX, methyl Lithium Phosphate (808)+TX, Toluene Fluorosulfonamide (810)+TX, Pyraclostrobin (821)+TX, Trichoderma harzianum (825)+TX, Tricyclazole (828)+TX, Azoline (838) ) +TX, triphenyltin (347) + TX, jinggangmycin (846) + TX, ketene (849) + TX, zinc (855) + TX, dimethyl dithioamine Zinc formate (856)+TX, benzoic acid amine (857)+TX, 1+TX, 1-bis(4-chlorophenyl)-2-ethoxyethanol (IUPAC-name) (910)+TX, 2+TX, diphenyl phenyl 4-benzenesulfonate (IUPAC-/Chemical Abstracts-Name) (1059)+TX, 2-fluoro- N -methyl- N- 1-naphthylacetamide (IUPAC-name (1295) + TX, 4-chlorophenylphenylhydrazine (IUPAC-name) (981) + TX, compound of formula B-5.1 + TX, compound of formula B-5.2 + TX, formula B-5.3 Compound + TX, with a compound of the formula B-5.4 + TX, a compound of the formula B-5.5 + TX, a compound of the formula B-5.6 + TX, a compound of the formula B-5.7 + TX, a compound of the formula B-5.8 + TX, a compound of the formula B-5.9 + TX, a compound of the formula B-5.10 + TX, a compound of the formula B-5.11 + TX, a compound of the formula B-5.12 + TX, a compound of the formula B-5.13 + TX, a compound of the formula B-5.14+TX, a compound of the formula B-5.15+TX, a compound of the formula B-5.16+TX, a compound B-5.17 and a compound B-5.18; a plant biological regulator selected from the group consisting of This group consists of: aralic acid benzene-S-methyl (6) + TX, chlormequat (137) + TX, ethephon (307) + TX, meperidine (509) and trinexarate Ethyl ester (841); an insecticide selected from the group consisting of abamectin (1) + TX, clothianidin (165) + TX, indomethacin - benzoate (291) + TX, guanamine (458) + TX, tefluthrin (769) + TX, thiamethoxam (792) + TX, and glyphosate (419) + TX, compound of formula D + TX flufenacetate + TX, and (B9) Spikes heteroaryl Farm (Isopyrazam) + TX, saddled Seda (Sedaxane) + TX, Compound of formula (E) + TX Compound of formula (F) + TX Further examples of particularly suitable mixtures are selected from the group consisting of Q: Group Q: Particularly suitable compositions according to the invention: a spore cocciin fungicide selected from the group consisting of: Azoxystrobin + TX, ether myramine + TX, fluoxastrobin + TX, ether oxystrobin + TX, phenoxystrobin + TX, acesulfame + TX, picoxystrobin + TX, pyraclostrobin ; trifloxystrobin and a compound of formula B-1.1; an azole fungicide selected from the group consisting of azaconazole + TX, chymazole + TX, cyproconazole + TX , difenoconazole + TX, diniconazole + TX, diniconazole M + TX, oxaconazole + TX, nitrile benzoxazole + TX, fluoroquinazole + TX, flucarbazole + TX, fluconazole + TX, hexaconazole + TX, imazalil + TX, hydrazol + TX, inobutazole + TX, meconazole + TX, myclobutanol + TX, mzoimidazole + TX, rice oxime ester + TX, penicillium Oxazole + TX, prochloraz + TX, propiconazole + TX, prothioconazole + TX, flurazol + TX, tebuconazole + TX, fluoroetherazole + TX, triazolone + TX, triazolol +TX, fluconazole + TX, sterilized azole + TX, benzyl chlorotriazol + TX, ethiazole + TX, furazolidazole + TX, furoseazole + TX and quinconazole + TX; selected from the group consisting of A fungicide, this group consists of 4-dodecyl-2,6-dimethyl Morpholine + TX, cycloalkanoline + TX, butyl morpholine + TX, tridemorpholine + TX, fenpropidin + TX, spiromycin + TX, powdery mildew and compounds of formula B-3.1; An anilinopyrimidine fungicide selected from the group consisting of cyprodinil + TX, azoxystrobin and pyrimethanil; a fungicide selected from the group consisting of Item composition: benzoxine + TX, benzophenidin + TX, benomyl + TX, biphenyl triazole alcohol + TX, pyridine azide + TX, captan dan + TX, rust rust + TX, ring Propionamide + TX, chlorothalonil + TX, copper + TX, cyanosin + TX, cymoxanil + TX, carbendazim + TX, dithianon + TX, famoxadone + TX, imidazo Ketone + TX, cyclosporin + TX, phenoxy carb + TX, seed dressing + TX, fluazinam + TX, fluorosis + TX, flubenamide + TX, sterilized Dan + TX, bismuth salt + TX , carbendazim + TX, iprodione + TX, guanidine urea + TX, mancozeb + TX, metalaxyl + TX, refined metalaxyl + TX, benomyl + TX, fluoropyrimidinol + TX, paclobutrazol + TX, pentocolon + TX, penthiopyramine + TX, procymidone + TX, propoxyquinol + TX, praziquantel + TX, quinoxaline + TX, thiocanthamide + TX , sulfur + TX, thiabendazole + TX, Fumei +TX, zocilazine + TX, tricyclazole + TX, compound +TX having the formula B-5.1, compound +TX having the formula B-5.2, compound +TX having the formula B-5.3, having the chemical formula B-5.4 Compound + TX, compound of formula B-5.5 + TX, compound of formula B-5.6 + TX, compound of formula B-5.7 + TX, compound of formula B-5.8 + TX, formula B-5.9 Compound +TX, compound +TX having the formula B-5.10 and compound +TX having the formula B-5.12; plant biological regulator selected from the group consisting of arsenic acid benzene-S-methyl+TX, chlormequat +TX, ethephon + TX, meperidine and anti-p-ethyl ester; insecticides selected from the group consisting of abamectin + TX, indomethacin - benzoate + TX, tefluthrin + TX, thiamethoxam + TX, and glyphosate + TX, a compound of formula D Floxacin + TX, and (B9) Isopyrazam + TX, Sedaxane + TX, compound of formula (E) + TX Compound of formula (F) + TX It has been found that the use of component (B) in combination with component TX surprisingly and in large amounts enhances the latter's effect against fungi and vice versa. Furthermore, the method of the invention is effective against a broader spectrum of such fungi that, when used alone, fights the active ingredients of such methods.

The active ingredient mixture of component TX and component (B) comprises a compound of formula I and additionally, other biocidally active ingredients or compositions or, if desired, preferably a solid or liquid adjuvant in the following mixing ratio : from 100:1 to 1:6000, especially from 50:1 to 1:50, more especially from 20:1 to 1:20, more especially from 10:1 to 1:10 Very especially in a ratio of from 5:1 to 1:5, especially preferred from 2:1 to 1:2, and a ratio from 4:1 to 2:1 is also preferred, most What is important is 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3: 2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2: 3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, Or 4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750 ratio. Those mixing ratios are understood to include, on the one hand, a weight ratio, and on the other hand, a molar ratio.

Surprisingly, it has been found that a specific weight ratio of component TX to component (B) can increase synergistic activity. Accordingly, a further aspect of the invention is a composition wherein component TX and component (B) are present in the composition in an amount that produces a synergistic effect. This synergistic activity is evident from the fact that the fungicidal activity of the composition comprising component TX and component (B) is greater than the sum of the fungicidal activity of component TX and component (B). This synergistic activity extends the range of action of component TX and component (B) in two ways. First, the application ratio of component TX and component (B) is reduced, while its effect remains equally good, which means that even in such a low application rate range, the two separate components have become generally ineffective. In this case, the active ingredient mixture still achieves a high degree of control of plant pathogens. Second, there is a substantial extension of the spectrum of plant pathogens that can be controlled.

There is a synergistic effect, whenever the combination of active ingredients is greater than the sum of the effects of the individual components. For a given active ingredient composition, the effect expected to be E follows the so-called COLBY formula and can be calculated as follows (COLBY, SR "Calculating the synergy and antagonisticity of herbicide compositions" "Weeds" ( Weeds), Vol. 15, pp. 20-22; 1967): ppm = milligrams of active ingredient (=ai) per liter of spray mixture

X = % effect of active ingredient using p ppm based on active ingredient A)

Y = % effect based on active ingredient B) using q ppm of active ingredient.

According to Colby (COLBY), the active ingredient of p+q ppm, the expected (additive) active ingredient A) + B)

If the actually observed (O) effect is greater than the expected effect (E), then the effect of the combination is super-additive, ie there is a synergistic effect. In mathematics, the synergy corresponds to the positive value of the difference of (O-E). In the case where the active (the expected activity) is added in a pure complementarity, the difference (O-E) is zero. The negative value of the difference (O-E) indicates a loss of activity compared to the expected activity.

However, in addition to the actual synergistic effect relative to fungicidal activity, the compositions according to the invention may have additional surprisingly advantageous properties. Examples of such advantageous properties that may be mentioned are: more favorable degradability; improved toxicological and/or ecotoxicological behavior; or improved characteristics of useful plants, including: emergence, cropping Yield, root system is more developed, tiller increases, plant height increases, leaves are larger, leaves at the base are less dead, tillers are stronger, leaves are greener, less fertilizer is needed, fewer seeds are needed, more tillers are produced, Early flowering, earlier grain ripening, less plant lodging, enhanced bud growth, improved plant vigor and early germination.

The composition according to the invention has a systemic action and can be used as a fungicide for foliar, soil, and seed treatment.

With the composition according to the invention it is possible to inhibit or destroy phytopathogenic microorganisms which occur on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of a plurality of different useful plants. The disease also protects parts of plants that grow later from being attacked by microorganisms that cause phytopathology.

The composition according to the invention may be applied to phytopathogenic microorganisms, useful plants, their locus, their propagation material, stored goods or technical materials threatened by microbial attack.

The composition according to the invention may be applied before or after the useful plant, its propagation material, the stored goods or the technical material is infected by the microorganism.

A further aspect of the invention is a method of controlling a disease caused by a plant pathogen on a useful plant or on a propagation material thereof, which comprises applying the composition according to the invention to a useful plant, a locus thereof or a propagation material thereof. Preferred are the methods comprising applying the composition according to the invention to a useful plant or to a locus thereof, more preferably to a useful plant. Further preferred is a method comprising applying a composition according to the invention to a propagation material of a useful plant.

Component (B) is known. Component (B) is included in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; 13th Edition; Editor: CDSTomLin (Tomlin); The British Crop Protection Council, which is described above for the specific component (B) under the number given in parentheses; for example, the compound "Avicidella" "" is described under the record number (1). Most of the components (B) are mentioned above by the so-called "common name", and the relevant "ISO common name" or another "common name" is used in individual cases. If the name is not a "common name", the nature of the alternately used name is given in parentheses for the specific component (B); in this case, the IUPAC name, IUPAC/Chemical Abstract name, "Chemical name" is used. ", "traditional name", "compound name" or "development code", or, if one of those names or "common name" is not used, the "alternative name" is used.

The following component (B) is registered as a CAS-registration number.

Fluconazole (86386-73-4), cis-fluconazole (112839-32-4), Fluxapyroxad (907204-31-3), imipenem (865318-97-4) ), flurazia (958647-10-4), isotianil (224049-04-1), downy mildew (283159-90-0), activated ester (126448-41-7), 1-A Base-cyclopropene (3100-04-7), glyphosate diammonium (69254-40-6), glyphosate dimethylammonium (34494-04-7), glyphosate isopropylammonium (38641- 94-0), glyphosate monoammonium (40465-66-5), glyphosate potassium (70901-20-1), potassium sesquisulfate (70393-85-0), glyphosate trimethyl sulphide ( 81591-81-3), glufosinate and its salts (51276-47-2, 35597-44-5 (S-isomer)), 4-dodecyl-2,6-dimethyl Aldimorph (CAS 91315-15-0); arsenate (CAS 1327-53-3); benzophenidin (CAS 98243-83-5); phenothiamine (CAS 413615-35-7) Cadmium chloride (CAS 10108-64-2); cedar leaf oil (CAS 8007-20-3); chlorine (CAS 7782-50-5); cinnamaldehyde (CAS: 104-55-2); copper ammonium carbonate (CAS 33113-08-5); copper oleate (CAS 1120-44-1); iodocarb (3-iodo-2-propynylbutylcarbamate) (CAS 55406-53-6); Moxacillin (CAS 10004-44-1); manganese dimethyldithiocarbamate (CAS 15339-36-3); mercury (CAS 7487-94-7; 21908-53-2; 7546-30- 7); benomyl (CAS 220899-03-6); neem oil (hydrophobic extract) (CAS 8002-65-1); epothilone CAS 248593-16-0); paraformaldehyde (CAS 30525 -89-4); penthiopyre (CAS 183675-82-3); phosphoric acid (CAS 7664-38-2); potassium bicarbonate (CAS 298-14-6); sodium bicarbonate (CAS 144-55- 8); sodium diacetate (CAS 127-09-3); sodium propionate (CAS 137-40-6); TCMTB (CAS 21564-17-0); and toluene sulfonamide (CAS 731-27-1).

Compound B-1.1 ("methionate") is described in EP-0-936-213; in US-6,020,332, CN-1-167-568, CN-1-155-977 and in EP-0 Compound B-3.1 ("Fluoromorpholine") in -860-438; Compound B-5.1 ("Dipropionin") in WO 01/87822; Compound B-5.2 in WO 98/46607; Compound B-5.3 ("fluopyram") in WO 99/42447; compound B-5.4 ("cycloflufenamide") in WO 96/19442; compound B- in WO 99/14187 5.5; Register compound B-5.6 ("pyribencarb") under CAS-registration 325156-49-8; compound B-5.7 ("carbazole fungicide" under CAS-registration 348635-87-0 Amine" or "ambromdole"; Compound B-5.8 (3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (2-dicyclopropyl-2) is described in WO 03/74491 -yl-phenyl)-guanamine; Compound B-5.9 (3-difluoromethyl-1-methyl-1H-pyrazole-4-) is described in WO 04/35589 and in WO 06/37632 Formic acid (9-isopropyl-1,2,3,4-tetrahydro-1,4-methyl bridge-naphthalen-5-yl)-decylamine); Compound B-5.10 (1) is illustrated in 03/10149 ,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxylic acid [2-(1,3-dimethylbutyl)phenyl]-decylamine) Registered under CAS-Registration 581809-46-3 and illustrated in WO 03/70705, Compound B-5.11 (3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3', 4 '-Dichloro-5-fluoro-1,1'-biphenyl-2-yl)-guanamine; bxixifen) ("bixafen")); registered under CAS-registration 658066-35-4 and at WO Compound B-5.12 (N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide is described in 04/16088 Amine; "fluopyramidine"); compounds B-5.13, B-5.14 and B-5.15 are described in WO 2007/17450; compounds B-5.16, B-5.17 and B are described in WO 2006/120219 -5.18; a compound of formula IV; a chemical formula is described, for example, in WO 04/067528, WO 2005/085234, WO 2006/111341, WO 03/015519, WO 2007/020050, WO 2006/040113, and WO 2007/093402; Compounds of V are described in WO 2001/094339; compounds B-21 are described in WO 2010/123791. It is described in WO 2004/035589, in WO 2006/037632 and in EP 1 556 385 B1, and is registered under the CAS-Reg. 881 685-58-1 Isopyraxam (3-(difluoromethyl) )-1-methyl- N- [1,2,3,4-tetrahydro-9-(1-methylethyl)-1,4-methylnaphthalen-5-yl]-1 H -pyrazole -4-carbamamine). Sedaxane ( N- [2-[1,1'-dicyclopropyl]-2-) is described in WO 2003/074491 and registered under CAS-Reg. 874967-67-6 Phenyl]-3-(difluoromethyl)-1-methyl-1 H -pyrazole-4-carboxamide); a compound of formula (VI) is described in WO 2008/014870; and in WO Compounds of formula (VII) are described in 2007/048556. Fomesafen was registered under CAS-Registration 72178-02-0.

3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (4'-methylsulfanyl-biphenyl-2-yl)-indole was registered under CAS No. 1021864-46-9 Amine (Compound B-5.19), registered under the CAS number 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (2-dichloromethylene-3-ethyl-1- Methyl-indoline-4-yl)-nonylamine (Compound B-5.20)

The composition according to the invention may also comprise more than one active ingredient (B), for example if it is desired to expand the disease control profile. For example, it may be advantageous to combine two or three components (B) with component TX in agricultural practice. An example is a composition comprising a compound of formula (I), azoxystrobin and cyproconazole.

In the above different list of active ingredients to be mixed with TX, the compound of formula I is preferably a compound of Table 2.

In the above mixture of the compound of the formula I (particularly selected from the compounds in Table 2) and other insecticides, fungicides, herbicides, safeners, adjuvants, etc., the mixing ratio thereof may be large. The range varies and is preferably from 100:1 to 1:6000, especially from 50:1 to 1:50, more particularly from 20:1 to 1:20, especially from 10:1 to 1:10. Those mixing ratios are understood to include, on the one hand, a weight ratio, and on the other hand, a molar ratio.

These mixtures can advantageously be used in the formulations mentioned above (in this case, the "active ingredient" relates to a mixture of corresponding TX and mixed partners).

Some mixtures may include a plurality of active ingredients which have significantly different physical, chemical or biological properties such that they are not readily self-contained for the same conventional Formulation type. In such cases, other types of formulations can be prepared. For example, when one active ingredient is a water-insoluble solid and the other is a water-insoluble liquid, it is still possible to disperse the solid active ingredient as a suspension (using a preparation method similar to SC) to activate the liquid. The ingredients are dispersed as an emulsion (using a preparation similar to EW) to disperse each active ingredient into the same continuous liquid phase. The resulting composition is a suspoemulsion (SE) formulation.

Mixtures comprising TX selected from Table 1 and one or more active ingredients as described above may be administered, for example, in the form of a single "water ready to use" in combination with a spray mixture (the mixture consisting of the individual active ingredients alone) Formulations (eg, "tank mix") are applied, and when applied in a sequential manner (ie, one after another suitable short period of time, such as hours or days), the individual active ingredients are used in combination Apply. The order in which the compound of formula I selected from Table 1 and the above active ingredients are administered is not critical to the practice of the invention.

The following non-limiting examples illustrate the invention described above in more detail and are not limiting thereof. Those skilled in the art will quickly recognize from the procedures the reagents and appropriate variants of the reaction conditions and techniques. All references mentioned herein are incorporated by reference in their entirety.

Preparation examples:

Throughout the examples, the depicted isomers are in excess in the reaction mixture and/or product.

Example 1: Preparation of P2

To a solution of I.1 (39 mg) in ethanol (2 mL) was added <RTI ID=0.0>> After stirring at reflux for 2 h, the ethanol was evaporated in vacuo. The residue was treated with sodium bicarbonate until pH 9 and extracted with ethyl acetate. The organic phase was dried with MgSO4, EtOAc (EtOAc)

Preparation of I1: To a solution of I9 (114 mg) in ethanol (10 mL) was added palladium over charcoal (5%; 10 mg). The reaction mixture was stirred for 3 h and 30 min under a hydrogen atmosphere. It was then filtered and evaporated to give a yellow oil (104 mg).

Preparation of I9: To a solution of I2 (117 mg) in dichloromethane (5 mL) was added triethylamine (37 uL). The reaction mixture was cooled to 0-5 ° C using an ice bath and methanesulfonium chloride (21 μL) was added. After stirring at 0-5 ° C for 30 min, the reaction mixture was stirred at ambient temperature for a further 4 days. It was quenched with saturated sodium bicarbonate solution and extracted with dichloromethane. The organic layer was washed with water, dried over magnesium sulfate and then concentrated. The residue was dissolved in tetrahydrofuran and 1,8-diazabicyclo[5.4.0]undec-7-ene (3 eq) was added. The reaction mixture Stir at ambient temperature for 5 days and then at 50 °C overnight. The reaction mixture was extracted with EtOAc EtOAc m. This material was used in the next step without further purification.

Preparation of I2: A freshly prepared lithium diisopropylamide solution (0.7 M; 30 mL) was added to a solution of I3 (4 g) cooled to -40 ° C in dry tetrahydrofuran (20 mL). After stirring at -20 ° C for 1 h, the reaction mixture was cooled to -40 ° C and the EtOAc (EtOAc <RTI ID=0.0> The reaction mixture was allowed to warm at ambient temperature, was quenched with EtOAc EtOAc (EtOAc)EtOAc. (2.6 g).

Preparation of I3: To a solution of 2-methyl-6,7-dihydro-5H-quinolin-8-one (10 g) in toluene (150 mL), EtOAc (6.24 mL) Sulfonic acid (1.07 g). The reaction mixture was stirred under reflux for 3 h using a Dean-Stark apparatus. Sodium hydroxide solution (0.5 M) was added and it was extracted with tri-butylmethyl ester. The organic phase was dried with MgSO4, EtOAc (EtOAc)

Example 2: Preparation of P9

Add a freshly prepared LDA solution (8 mL; in THF) to a solution of 6,6'-dimethyl-[2,2']dipyridyl (250 mg) in dry THF (6 mL) at -65 °C 0.18 M solution). After stirring at -65 ° C for 45 min, diiodomethane (55 μL) dissolved in dry THF (3 mL) was slowly added. The reaction mixture was stirred at -65 °C for 1 h and then allowed to warm slowly to -30 ° C for 1 h. The reaction was then quenched with ammonium chloride solution and further stirred until ambient temperature was reached. The reaction mixture was extracted with ethyl acetate. The organic phase was washed with aq. ammonium chloride, dried over magnesium sulfate and purified with silica gel to afford white crystals (126 mg).

Example 3: Preparation of P7

O-methylhydroxylamine hydrochloride (47 mg) was added to a solution of I4 (90 mg) in ethanol (2 mL) and HCl (2 N; 1 mL). After stirring at reflux for 2 h, the solvent was evaporated. The residue was treated with a bicarbonate solution until pH 9 and extracted with ethyl acetate. The organic phase was washed with water, dried over MgSO4

Preparation of I4: To a solution of 6-methyl-[2,2']dipyridyl (170 mg) in dry THF (6 mL) was added freshly prepared LDA solution (1.05 mL; 1 M in THF) ). After stirring at -20 ° C for 30 min, this mixture was added to 2-(2-bromo-ethyl)-6-(2-methyl-[1,3]dioxolan-2-yl at -20 °C. )-pyridine (272 mg) in a solution in dry THF. The reaction mixture was stirred at -20 °C for an additional 45 min and at ambient temperature for 30 min then quenched with EtOAc EtOAc. This was extracted with methylene chloride. EtOAc (EtOAc)EtOAc. LC-MS (OA_5min_45V): 1.04min, 362([M+1] ⁺ )

Preparation of 2-(2-bromo-ethyl)-6-(2-methyl-[1,3]dioxolan-2-yl)-pyridine: 2-[6-(2-methyl- [1,3]dioxolan-2-yl)-pyridin-2-yl]-ethanol (3.4 g, 10.78 g) was added tetrachloromethane (10.78 g) in dichloromethane (170 mL) and A solution of triphenylphosphine (8.51 g) in dichloromethane (80 mL) was then added dropwise. After stirring at ambient temperature for 2 h, the reaction was quenched with ammonium chloride solution at 0 °C. This was extracted with methylene chloride, dried (MgSO4), evaporated ¹ H-NMR (CDCl ₃ , 400 MHz): 7.65 (t, 1H), 7.45 (d, 1H), 7.15 (d, 1H), 4.15 (m, 2H), 3.95 (m, 2H), 3.8 (t) , 2H), 3.4 (t, 2H), 1.75 (s, 3H).

Preparation of 2-[6-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-ethanol: [6-(2-methyl-) at 0 °C Add lithium hydride solution (50 mL; 1 M) to [1,3]dioxolan-2-yl)-pyridin-2-yl]-acetic acid ethyl ester (5 g) in THF (100 mL) THF solution). After stirring at 0 ° C for 30 min, then at ambient temperature for 2 h, the reaction was quenched with water then sodium hydroxide solution (0.5 M). The suspension was filtered and rinsed with THF. The filtrate was concentrated under vacuum and then purified using EtOAc to give 2-[6-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-ethanol (3.4) g). ¹ H-NMR (CDCl ₃ , 400 MHz): 7.65 (t, 1H), 7.45 (d, 1H), 7.1 (d, 1H), 4.1 (m, 2H), 4.05 (t, 2H), 3.9 (m) , 2H), 3.05 (t, 2H), 1.75 (s, 3H).

Preparation of [6-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-acetic acid ethyl ester: 2-methyl-6-(2-methyl -[1,3]dioxolan-2-yl)-pyridine (4 g) was added dropwise to a solution of -180 ° C in THF (20 mL), freshly prepared LDA solution (20 mL; 2.35 M) THF solution). After stirring at -60 ° C for 20 min, stirring at -40 ° C for 1 h and stirring at -30 ° C for more than 1 h, the reaction mixture was cooled to -60 ° C and added with diethyl carbonate dissolved in THF (8 mL) Ester (12 g). The reaction mixture was stirred at -40 °C for 20 min and allowed to warm slowly to ambient temperature overnight. The reaction was then quenched with EtOAc (EtOAc)EtOAc. ¹ H-NMR (CDCl3, 400 MHz): 7.7 (t, 1H), 7.45 (d, 1H), 7.25 (d, 1H), 4.2 (m, 2H), 4.1 (m, 2H), 3.9 (m, 2H), 1.75 (s, 3H), 1.25 (t, 3H).

Preparation of 2-methyl-6-(2-methyl-[1,3]dioxolan-2-yl)-pyridine: 1-(6-methyl-pyridin-2-yl)-ethanone (20 g) Ethylene glycol (55 g) and p-toluenesulfonic acid (2.55 g) were added to a solution in toluene (400 mL). The reaction mixture was heated under reflux for 24 h using a Dean-Stark apparatus. Allow it to return to ambient temperature and add sodium hydroxide solution (150 mL; 0.5 M). This was extracted with methylene chloride, washed with water and dried over magnesium sulfate. ¹ H-NMR (CDCl ₃ , 400 MHz): 7.55 (t, 1H), 7.35 (d, 1H), 7.05 (d, 1H), 4.1 (m, 2H), 3.9 (d, 1H), 2.55 (s) , 3H), 1.75 (s, 3H).

Example 4: Preparation of P13

Manganese dioxide (37.92 g) was added to a solution of I5 (20 g) in chloroform (600 mL). The reaction mixture was stirred at 60 ° C for 72 h. The presence of the starting material indicated that the reaction had not yet been completed, and therefore more manganese dioxide was added and the reaction mixture was stirred at 60 ° C for an additional 24 h. The reaction mixture was filtered and washed with dichloromethane. The residue was concentrated in vacuo and purified with EtOAc EtOAc (EtOAc)

Preparation of I5: To a solution of I6 (1 g) in isopropanol (15 mL) was added thiourea (0.92 g) and 2-aminobenzylamine (2.46 g). The reaction mixture was heated in a microwave at 165 °C for 30 min. It was then poured into a saturated bicarbonate solution, extracted with ethyl acetate and washed with brine. The organic phase was dried with sodium sulfate and concentrated in vacuo to give crystallite This material was used in the next step without further purification.

Preparation of I6: A solution of I7 (27.3 g, from the crude product described below) in dichloromethane was stirred at ambient temperature overnight. Dimethylaminoformamidine chloride (30.6 g) was added and trimethylsulfonyl cyanide (35.6 mL) was added in portions (caution exotherm). The reaction mixture was stirred at ambient temperature overnight, then the reaction was quenched with a carbonate solution and at pH 9 Extraction was carried out with dichloromethane and then with brine. The organic phase was dried with EtOAc (EtOAc)EtOAc.

Preparation of I7: mCPBA (129.7 g) was added portionwise to a solution of I8 (54.2 g, crude product from below) in chloroform (700 mL). The reaction mixture was stirred at 45 ° C for 2 h, then the reaction was carefully quenched with sodium hydroxide solution (10 M) at 0-5 ° C until basic pH was reached and then sodium thiosulfate was used Quenched. It was extracted with dichloromethane (three times) and washed with brine. The organic phase was dried with sodium sulfate and concentrated in vacuo to give a crystallite. This material was used in the next step without further purification.

Preparation of I8: nBuLi (100 mL; 2.5 M in hexane) was added dropwise to 2-methylpyridine (400 mL) cooled at -20 ° C under argon. The reaction mixture was stirred at -20 ° C for 1 h, and a solution of 2-ethylpyridine in THF (100 mL) was added dropwise via EtOAc at -20 ° C. The reaction mixture was stirred overnight and allowed to warm slowly. Ambient temperature. It was reheated for 3 h at 50 ° C and the reaction was quenched with ammonium chloride solution at ambient temperature and stirred for 30 min. The reaction mixture was extracted with ethyl acetate and washed with brine. Drying over sodium sulphate, EtOAc (EtOAc m.

Example 5: Preparation of P20

A solution of P19 (92 mg; 0.224 mmol) in dimethylformamide (5 mL) was cooled to EtOAc. Sodium hydride (11 mg; 0.269 mmol) was added and the obtained compound was stirred at this temperature for one hour. The reaction mixture was allowed to recover at ambient temperature and methyl iodide (0.015 mL; 0.235 mmol). LC-MS analysis was carried out after the reaction, which showed that the starting material remained at this time. The reaction mixture was again cooled to 0.degree. C., additional sodium hydride (11 mg; 0.2. This was repeated twice because the reaction control showed the remainder of the starting material. The reaction mixture was carefully poured into water and extracted with ethyl acetate. The organic phase was washed with EtOAc (EtOAc m.

Preparation of P19: A solution of P18 (0.279 g; 0.616 mmol) in tetrahydrofuran (5 mL) was cooled to -78. Lithium aluminum hydride (1 M in THF, 0.74 mL; 0.74 mmol) was added dropwise and the mixture was stirred at this temperature for 3 hr. Reaction control showed the starting material remained and then additional lithium aluminum hydride (1 M in THF, 0.308 mL; 0.308 mmol). After 30 minutes, the reaction control showed that all starting materials were consumed. Allow the reaction mixture at 0 ° C It was recovered and quenched with saturated sodium bicarbonate (1.sub.2 mL), filtered and concentrated in vacuo. The residue was redissolved in EtOAc (EtOAc)EtOAc. This intermediate was used in the next step without purification.

Preparation of P18: P17 (0.398 mg; 0.759 mmol) and water (0.12 mL) were added to a suspension of sodium chloride (67 mg; 1.138 mmol) in dimethyl hydrazine (5 mL) under argon. . The resulting mixture was stirred at reflux overnight. The reaction mixture was poured into brine (10 mL) and extracted with ethyl acetate (3×10 mL). The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by EtOAc EtOAc (EtOAc)

Preparation of P17: Preparation was carried out following the literature procedure (Inorganic Chemistry, 1983, 22, 171-174). Sodium hydride (180 mg; 4 mmol) was added to a cooled solution of diethyl malonate (240 mg; 2 mmol) in dry tetrahydrofuran (5 mL). This reaction mixture was allowed to recover at ambient temperature and stirred for 30 minutes. The reaction mixture was then cooled to 0 ° C with ice bath and 6'-chloromethyl-6-methyl-[2,2']dipyridine was added dropwise. A solution of the base (943 mg; 4 mmol) in dry tetrahydrofuran (5 mL) followed by sodium iodide (593 mg; 4 mmol). The resulting mixture was stirred at ambient temperature overnight. The reaction mixture was then poured into ice water and acidified with 2N aqueous HCI. After stirring for 10 minutes, the pH was adjusted to 7 by using a 2N aqueous NaOH solution and extracted with dichloromethane. The organic phase was washed with water and brine, dried over magnesium sulfate. The crude material was purified by silica gel chromatography to give white crystals (418 mg).

Preparation of chloromethyl-6-methyl-[2,2']dipyridyl: 6,6'-dimethyl-[2,2']dipyridyl (1.88 g; 10 under argon atmosphere) Methyl) was dissolved in tetrachloromethane (50 ml). N-Chlorosuccinimide (1.36 g; 10 mmol) and benzamidine peroxide (50 mg; 0.67 mmol) were added. The reaction mixture was stirred at reflux overnight. The mixture was cooled with an ice bath, filtered, and the filtrate was concentrated in vacuo. The crude material was purified by silica gel chromatography to give white crystals (950 mg).

Example 6: Preparation of P15

MeMgBr (4.87 mL; 1 M in THF) was added dropwise to a solution of I10 (510 mg) at 0 °C. After stirring at 0 ° C for 30 min, ethanol (16 mL) was added. O-methyl-hydroxylamine hydrochloride (217 mg) was then added and the reaction mixture was heated to 55 °C for 30 min. The solvent was then removed and the residue was diluted with ethyl acetate. The organic phase is then washed with brine, dried over sodium sulfate, filtered and concentrated and purified with EtOAc A yellow oil (480 mg) was obtained.

Preparation of I10: Lithium chloride (219 mg) was added to a solution of I11 (400 mg) in dimethyl hydrazine. After stirring at 180 ° C for 15 h, the reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with EtOAc (EtOAc)EtOAc.

Preparation of I11: Sodium hydride (103 mg; 60% in oil) was added to a solution of I12 (1.1 g) in tetrahydrofuran (15 mL). After stirring at ambient temperature for 1 h, a solution of 6-vinylpyridine-2-carbonitrile (310 mg) in tetrahydrofuran (5 mL) was slowly added. After stirring at ambient temperature for 2 h, the reaction mixture was poured into water and ethyl acetate. The organic phase was washed with water, dried (MgSO4) Pyridine)-2-pyridine]ethyl butyrate (740 mg).

Preparation of I12: Lithium diisopropylamide (310 mL; 2 M solution in tetrahydrofuran) was added to 6,6'-dimethyl-2 under argon at -60 ° C over 1 h. , 2'-Dipyridine (53.00 g) and a mixture of diethyl carbonate (102 mL) in tetrahydrofuran (27 mL). After stirring for an additional 15 min at -60 °C, ammonium chloride solution (50 mL; 25% in water) was carefully added. The reaction mixture was then poured into water and extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate, concentrated and purified with EtOAc.

Example 7: Preparation of P46:

Acetylacetone (0.33 g) was added to I13 (500 mg) in pyridine (4.8 mL). After stirring at 70 ° C for 16 h, acetonitrile acetone (0.66 g) was added and the mixture was stirred at 80 ° C for further 4 h. The reaction mixture was then concentrated and the residue was purified eluting elut elut

Preparation of I13: sodium methoxide (2 mL; 5.4 M in methanol) was added to 6-[3-[6-(6-methyl-2-pyridine)-2-pyridinyl]propyl]pyridine-2- In a solution of nitrile (1.35 g). After stirring for 1 h at ambient temperature, ammonium chloride (0.804 g) was added and stirred for additional 20 h then the mixture was concentrated and the residue was suspended in diethyl ether and filtered to give the hydrochloride The product is given together with an excess of ammonium chloride. This material was used in the next step without further purification.

Example 8: Preparation of P23

Will Na ₂ CO ₃ . 10 H ₂ O (2.35 g, 8.13 mmol) and 6-methyl-pyridine-2-carboxamidine hydrochloride (670 mg, 3.90 mmol) were added sequentially to I14 (547 mg, 1.63 mmol) in THF (25 mL) In a brown solution. The reaction mixture was heated to reflux temperature and stirred for 3 h. After cooling to room temperature, the crude product was purified by EtOAc EtOAc (EtOAc:EtOAc: LC-MS (Method _{ZCQ) R t = 1.68 min,} MS:. (M + +1) = 571. ¹ H-NMR (CDCl ₃ , 400 MHz): 2.49 (m, 2H); 2.72 (s, 6H); 3.13 (m, 4H); 7.16 (dd, 2H); 7.28 (s, 2H); , 2H); 7.48 (m, 2H); 7.74 (m, 4H); 8.34 (m, 4H).

(15mL) at room temperature under argon, _{Pd (PPh 3) 2 Cl 2} (45.8 mg, 0.065 mmol) and CuI (24.9 mg, 0.13 mmol) was dissolved in degassed THF: Preparation of I14. Then Et ₃ N (0.41 g, 4.07 mmol) and 2-fluoro-benzylguanidine chloride (0.39 mL, 3.26 mmol) and hept-1,6-diyne (150 mg, 1.63 mmol) were added sequentially to the solution. . The dark brown mixture was stirred overnight. This intermediate (in solution) was used in the next step without purification.

Example 9: Preparation of I15

I16 (0.2 g, 0.98 mmol), vinyl tributylstannane (0.32 mL, 1.08 mmol), cesium fluoride (0.3 g, 1.95 mmol), tetrakis(triphenylphosphine)palladium(0) (57 mg, A mixture of 0.05 mmol) and copper (I) iodide (19 mg, 0.10 mmol) in dimethylformamide (4 mL) was stirred at 85 ° C overnight. The suspension was filtered through Hyflo after addition of ethyl acetate and water. The organic layer was separated, washed with brine, dried over sodium sulfate and evaporated. The residue was purified with hydrazine (using heptane/ethyl acetate 19:1 then dichloromethane/ethanol 99:1 as eluent) to give 6-methyl-6' as a beige powder. Vinyl-(2,2') dipyridine, mp 62 ° C - 63 ° C.

Preparation of I16: 6,6'-Dichloro-(2,2') dipyridine (2.5 g, 44.4 mmol; 2.5 J. Chem. Soc. Perkin I 1980) , 2527); Organic News (Org. Lett. 2000, 803)) with iron(III) pyruvate (1.57 g, 4.44 mmol) in tetrahydrofuran (200 mL) with 1-methyl-2-pyrrolidine Methyl magnesium bromide (34.1 mL, 102 mmol; 3.0 M in diethyl ether) was added dropwise to the suspension in ketone (25 mL) and stirring was continued for 30 min. The suspension was filtered through Hyflo after addition of ethyl acetate and water. The organic layer was separated, washed with brine, dried over sodium sulfate and evaporated. The residue was purified with oxime (using dichloromethane/ethanol 98:2 as eluent) to give 6-chloro-6'-methyl-(2,2')dipyridine as a white powder. Mp 135 ° C - 136 ° C.

Example 10: Preparation of I17

Triethylamine (1.09 g) and palladium (50 mg; 10% in carbon) were added to a solution of I18 (1.15 g) in tetrahydrofuran (20 mL). After stirring for 6 h under a hydrogen atmosphere, EtOAc EtOAc m.

Preparation of I18: Phosphorous oxychloride (2.67 g) was slowly added to I19 (3.14 g) in toluene (25 mL). The green suspension was stirred at 70 ° C for 90 min. The reaction mixture was cooled to ambient temperature and poured into a sodium bicarbonate solution (100 mL; 20% in water). After stirring for 15 min at room temperature, the reaction mixture was extracted with ethyl acetate, the combined organic phases were washed with water, dried over MgSO _4, filtered and concentrated to give a brown solid (3.29 g).

Preparation of I19: 6-methylpyridine-2-carboxamidine hydrochloride (15 g) was suspended in ethanol (200 mL). A third grade potassium butoxide (11.149 g) was slowly added at ambient temperature. Dimethyl-1,3-acetone dicarboxylate (16.742 g) was then added dropwise and the reaction mixture was heated to reflux for 18 h. The reaction mixture was concentrated and the green residue was taken up in ethyl acetate and water. Hydrochloric acid (2 N in water) was added until pH 7, then the aqueous phase was extracted with ethyl acetate. Dried and concentrated and the combined organic phases over MgSO _4. The solid residue was suspended in heptane, filtered and dried to give a green solid (20.7 g).

Example 11: Preparation of I29

To a suspension of 75 mg (1.88 mmol) of sodium hydride (60%) in 6 ml of dimethylformamide at 0 ° C, 0.14 ml (1.88 mmol) in 2 ml of dimethylformamide )acetone. After 0.5 h, 0.4 g (1.57 mmol) of 1-(6-bromo-pyridin-2-yl)-3-dimethylamino-propenone in 2 ml of dimethylformamide was added dropwise at 0 °C. (Tetrahedron Lett. 2003, 6305) and the solution was stirred for 1 h. An additional 40 mg of sodium hydride (60%) was added and stirring was continued for 1 h. Then 145 mg (1.88 mmol) of ammonium acetate was added at 0 °C. 6 ml of acetic acid was added dropwise and the reaction mixture was heated to 125 ° C for 5 min. After cooling, the reaction mixture was poured into a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and evaporated in vacuo. The residue was purified with hydrazine (using heptane / ethyl acetate 9:1 as eluent) to give 6-bromo-6'-methyl-(2,2')dipyridine as a white powder. , mp 148 ° C - 149 ° C.

Example 12: Preparation of I30

I18 (4.3 g, 15 mmol) was dissolved in methanol (80 mL) and sodium MeOH (EtOAc, EtOAc, After stirring at room temperature for 4 h, HCl 6 N (6 mL, 6 N in water) was added and volatiles were removed. The residue was dissolved in ethyl acetate and neutralized with sodium hydroxide (2N in water). The mixture was extracted with EtOAc (EtOAc)EtOAc.

Example 13: Preparation of I31

I18 (4.3 g, 15 mmol) was dissolved in tetrahydrofuran (78 mL) and 1-methyl-2-pyrrolidone (11 mL) and ethyl acetate (0.52 g, 1.5 mmol). 3 M methylmagnesium bromide in diethyl ether (12 g, 11 mL, 34 mmol) was added dropwise over 1 h (temperature increased up to 33 ° C). After stirring at ambient temperature for 45 min, 3 M methylmagnesium bromide in diethyl ether (6 mL) was added dropwise over 10 min. The reaction mixture was stirred at ambient temperature for 2 h, quenched with water and diluted with EtOAc. This compound was filtered, and the organic phase was separated, dried over magnesium sulfate, filtered and concentrated. The residue was purified with EtOAc (EtOAc) (EtOAc)

Example 14: Preparation of I40:

Sodium methoxide (0.207 g) was added to a solution of 4,6-dibromo-2-(6-methyl-2-pyridyl)pyrimidine (I39, 0.300 g) in tetrahydrofuran. After stirring at room temperature for 5 min, hydrochloric acid (1 M in water) was added and the mixture was extracted with ethyl acetate. The combined organic layers were dried with EtOAc EtOAc EtOAc.

Preparation of I39: Phosphorus oxybromide (V) (4.2 g) was added to 2-(6-methylpyridin-2-yl)pyrimidine-4,6-diol (CAS NO 1001915-36-1) (1.0 g) In a suspension in toluene (2.5 ml). After stirring at 120 <0>C for 3 h, the reaction mixture was cooled, diluted with methylene chloride, and carefully quenched with sodium bicarbonate (20% in water) and extracted with dichloromethane. The combined organic layers were dried with EtOAc EtOAc EtOAc.

Example 15: Preparation of P65:

Sodium hydride (0.32 g; 60% in oil) was added in one portion to a solution of I12 (3.57 g) in tetrahydrofuran (60 mL). After stirring at ambient temperature for 1 h, a solution of I20 (1.4 g) in tetrahydrofuran (20 mL) was added dropwise over 20 min. After stirring at ambient temperature for 2 h, the~~~~~~~~~~ The combined organic phases were dried with EtOAc EtOAc (EtOAc)

Preparation of I12: a mixture of I24 (2.3 g), vinyltributylstannane (3.037 g, 2.799 mL) and tetrakis(triphenylphosphine)palladium(0) (400 mg) in toluene (30 mL) Stir at 100 ° C overnight. The reaction mixture was cooled to room temperature and sodium hydroxide (20 mL, 1 M in water) was added. The mixture was stirred vigorously for 3 h and then diluted with ethyl acetate. The organic phase was separated, dried over magnesium sulfate, filtered and concentrated. The residue was purified with EtOAc (EtOAc)

Preparation of I24: a mixture of 6-bromopyridine-2-guanidine hydrochloride (CAS 122918-17-6) (6.0 g), acetonitrile acetone (7.8 mL, 7.6 g) and pyridine (51 mL) at 70 ° C Stir overnight. The reaction mixture was concentrated and the residue was purified using EtOAc to give white solid. Body (4.3g).

LC-MS method used Method ZDQ

ZQ mass spectrometer (single-phase quadrupole mass spectrometer) from Waters: ionization method: electrospray; polarity: positive ion and negative ion; capillary (kV) 3.00; cone (C) (V) 30.00; extractor (V): 2.00; source temperature (°C) 150; desolvation gas temperature (°C) 250; cone backflush gas flow (L/Hr) 50; desolvation gas flow (L/Hr) 400, mass range: 100 to 900 Da.

HP 1100 HPLC from Agilent: solvent degassing unit, binary pump, heated column chamber and diode array detector; column: Phenomenex Gemini C18, 3 μm, 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

Method ZCQ

ZQ mass spectrometer from Waters (single-phase quadrupole mass spectrometer)

Instrument parameters:

Ionization method: electric sprinkler

Polarity: positive ion

Capillary (kV) 3.00, cone (V) 30.00, extractor (V) 2.00, source temperature (°C) 100, desolvation gas temperature (°C) 250, cone backflush gas flow (L/Hr) 50, solvent removal Airflow (L/Hr) 400

Quality range: 100 to 900 Da

HP 1100 HPLC from Agilent: solvent degasser, quaternary pump (ZCQ) / binary pump (ZDQ), heated column chamber and diode array detector.

Column: Phenomenex Gemini C18, 3 mm particle size, 110 Å, 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

OA_2min_30V

SQD mass spectrometer from Waters (single-phase quadrupole mass spectrometer): ionization method: electrospray; polarity: positive and negative ions; capillary (kV) 3.00; cone (V) 30.00; extractor (V): 2.00: Source temperature (°C): 150; desolvation gas temperature (°C): 250; cone backflush gas flow (L/Hr)0; desolvation gas flow (L/Hr): 650, mass range: 100 to 900 Da

Acquity UPLC from Waters: Binary pump, heated column chamber and diode array detector; solvent degasser, binary pump, heated column chamber and diode array detector; column: Phenomenex Gemini C18 , 3 μm, 30 × 2 mm; temperature: 60 ° C; DAD wavelength range (nm): 210 to 500

Solvent gradient:

A=H ₂ O+5% MeOH+0.05% HCOOH

B = acetonitrile + 0.05% HCOOH

OA_2min_45V

SQD mass spectrometer from Waters (single-phase quadrupole mass spectrometer): ionization method: electrospray; polarity: positive ion and negative ion; capillary (kV) 3.00; cone (V) 45.00; extractor (V): 2.00; Source temperature (°C): 150; desolvation gas temperature (°C): 250; cone backflush gas flow (L/Hr)0; desolvation gas flow (L/Hr): 650, mass range: 100 to 900 Da

Acquity UPLC from Waters: Binary pump, heated column chamber and diode array detector; solvent degasser, binary pump, heated column chamber and diode array detector; column: Phenomenex Gemini C18 , 3 μm, 30 × 2 mm; temperature: 60 ° C; DAD wavelength range (nm): 210 to 500

Solvent gradient:

A=H ₂ O+5% MeOH+0.05% HCOOH

B = acetonitrile + 0.05% HCOOH

Time A% B% flow rate (mL/min)

OA_3min_30V

ZQ mass spectrometer (single-phase quadrupole mass spectrometer) from Waters: ionization method: electrospray; polarity: positive ion and negative ion; capillary (kV) 3.00; cone disk (V) 30.00; extractor (V): 2.00; Source temperature (°C): 100; desolvation gas temperature (°C): 250; cone blowback gas flow (L/Hr) 50; desolvation gas flow (L/Hr): 400, mass range: 100 to 900 Da

HP 1100 HPLC from Agilent: Solvent degasser, binary pump, heated column chamber and diode array detector; column: Phenomenex Gemini C18, 3 μm, 30 × 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

OA_5min_45V

SQD mass spectrometer from Waters (single-phase quadrupole mass spectrometer)

Ionization method: electrospray; polarity: positive ion and negative ion; capillary (kV) 3.00; cone (V) 45.00; extractor (V): 2.00; source temperature (°C): 150; desolvation gas temperature (°C): 250; cone backflush gas flow (L/Hr)0; desolvation gas flow (L/Hr): 650, mass range: 100 to 900 Da

Acquity UPLC from Waters: Binary pump, heated column chamber and diode array detector; solvent degasser, binary pump, heated column chamber and diode array detector; column: Phenomenex Gemini C18 , 3 μm, 30 × 2 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

OA_8min_Pol_30V

ZQ mass spectrometer from Waters (single-phase quadrupole mass spectrometer)

Ionization method: electrospray; polarity: positive ions and negative ions; capillary (kV) 3.00; Cone disk (V) 30.00; extractor (V): 2.00; source temperature (°C): 100; desolvation gas temperature (°C): 250; cone backflush gas flow (L/Hr) 50; desolvation gas flow (L /Hr): 400, mass range: 100 to 900 Da

HP 1100 HPLC from Agilent: solvent degasser, binary pump, heated column chamber and diode array detector; column: HyperCarb, 3 μm, 30 × 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

Method U and UPLC1

ACQUITY SQD Mass Spectrometer from Waters (Single Phase Quadrupole Mass Spectrometer)

Ionization method: electric sprinkler

Polarity: positive ion

Capillary (kV) 3.00, cone (V) 20.00, extractor (V) 3.00, source temperature (°C) 150, desolvation gas temperature (°C) 400, cone backflush gas flow (L/Hr) 60, desolvent Airflow (L/Hr) 700

Quality range: 100 to 800 Da

DAD wavelength range (nm): 210 to 400

Method Waters ACQUITY UPLC using 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 μm; temperature: 60 °C.

OA_ standard

ZQ mass spectrometer from Waters (single-phase quadrupole mass spectrometer)

Instrument parameters:

Ionization method: electric sprinkler

Polarity: positive and negative ions

Capillary: 3.00 Kv

Cone disk: 30 V

Extractor: 2.00 V

Source temperature: 150 ° C,

Desolvation gas temperature: 350 ° C

Cone blowback airflow: 50 L/Hr

Desolvent flow: 400 L/Hr

Quality range: 100 to 900 Da

Acquity UPLC from Waters: Binary pump, heated column chamber and diode array detector.

Solvent degasser, binary pump, heated column chamber and diode array detector.

Column: Waters UPLC HSS T3, 1.8 □ m, 30 × 2.1 mm,

Temperature: 60 ° C

DAD wavelength range (nm): 210 to 500

Solvent gradient:

A=H ₂ O+5% MeOH+0.05% HCOOH

B = acetonitrile + 0.05% HCOOH

Biological examples:

Phytophthora infestans/tomato/leaf disc prevention method (late blight): Place the tomato leaf disc on water agar in a multiwell plate (24-well format) and prepare it in water at a rate of 200 ppm. The test compound was sprayed. After 1 day of application, the leaf discs were inoculated with a spore suspension of the fungus. The inoculated leaf discs were incubated in a climatic chamber at 24 h dark, followed by a 12/12 h (lighting/dark) light protocol at 16 ° C and 75% relative humidity, and the compound activity was evaluated as Percentage of disease control compared to untreated when appropriate levels of disease damage occurred in untreated control leaf discs (5-7 days after administration). The following compounds produced at least 80% control of Phytophthora infestans : P08; P02; P22; P34; P38; P40; P47; P48; P49; P.54; P.60;

Plasmopara viticola /grape/leaf disc prevention (late blight): Vine leaf discs were placed on water agar in a multi-well plate (24-well format) and sprayed with the formulated test compound diluted in water. After 1 day of application, the leaf discs were inoculated with a spore suspension of the fungus. The inoculated leaf discs were incubated in a climate chamber under a 12/12 h (lighting/dark) light protocol at 19 ° C and 80% relative humidity, and compound activity was evaluated as in the untreated control. Percentage of disease control compared to untreated when appropriate levels of disease damage occurred in the leaf discs (6-8 days after administration). The following compounds produced at least 80% control of Plasmopara viticola: P12; P08; P09; P03; P04; P15; P20; P22; P27; P35; P36; P41; P42; P44; P47; P48; ;P.67

Puccinia recondita f.sp tritici / wheat/leaf disc prevention (brown rust): The wheat leaf fragment of the cultivar (cv) Kanzler was placed on agar in a 24-well plate at 200 ppm The application rate was sprayed with the formulated test compound diluted in water. After 1 day of application, the leaf discs were inoculated with a spore suspension of the fungus. The inoculated leaf fragments were incubated in a climate chamber under a 12/12 h (lighting/dark) light protocol at 19 ° C and 75% relative humidity, and compound activity was assessed as untreated control leaves. The percentage of disease control compared to untreated when an appropriate level of disease damage occurred in the fragment (7-9 days after administration). The following compounds produced at least 80% control of Puccinia striiformis: P12; P14; P01; P08; P09; P07; P02; P03; P04: P16; P18; P19; P20; P22; P23; P27; P30; P31 ;P32;P33;P34;P37;P38;P39;P40;P41;P42;P43;P44;P45;P47;P48;P49;P50;P51;P.54;P.59;P.60;P.61 ;P.62;P.67

Puccinia reticulata /wheat/leaf disc treatment (brown rust): The wheat leaf fragment of cv Kanzler was placed on agar in a 24-well plate. The leaf fragments are inoculated with a spore suspension of the fungus. The plates were stored in the dark at 19 ° C and 75% relative humidity. After 1 day of inoculation, the formulated test compound diluted in water was applied at an application rate of 200 ppm. The inoculated leaf fragments were incubated in a climate chamber under a 12/12 h (lighting/dark) light protocol at 19 ° C and 75% relative humidity, and compound activity was assessed as untreated control leaves. The percentage of disease control compared to untreated when an appropriate level of disease damage occurred in the fragment (6-8 days after administration). The following compounds produced at least 80% control of Puccinia striiformis: P14; P01; P08; P07; P09; P02; P03; P16; P18; P19; P20; P22; P23; P30; P33; P34; P38; P39 ;P40;P41;P42;P44;P45;P47;P48;P49;P50;P51;P.54;P.59;P.60;P.61;P.62;P.66;P.67

Phaeosphaeria nodorum (Septoria nodorum) / wheat/leaf disc prevention (bilt blight): cv Kanzler's wheat leaf fragment was placed on agar in 24-well plates and used at an application rate of 200 ppm The formulated test compound diluted in water was sprayed. After 2 days of application, the leaf discs were inoculated with a spore suspension of the fungus. The inoculated test leaf discs were incubated in a climate chamber under a 12/12 h (lighting/dark) light protocol at 20 ° C and 75% relative humidity, and the compound activity was evaluated as untreated. Percentage of disease control compared to untreated when appropriate levels of disease damage occurred in control leaf discs (5-7 days after administration). The following compounds produced at least 80% control of A. sphaeroides: P12; P13; P14; P01; P08; P09; P10; P02; P03; P04; P15; P16; P17; P18; P19; P20; P21; P22 P23;P24;P25;P26;P27;P28;P29;P31;P32;P33;P34;P37;P38;P39;P40;P41;P42;P43;P44;P45;P47;P48;P49;P50;P51; P.53; P.54; P.59; P.60; P.61; P.62; P.66; P.67

Pyrenophora teres / barley / leaf disc prevention (net blotch): The barley leaf fragment of cv Hasso was placed on agar in a 24-well plate and diluted in water at an application rate of 200 ppm. The formulated test compound was sprayed. After 2 days of application of the test solution, the leaf fragments were inoculated with a spore suspension of the fungus. The inoculated leaf fragments were incubated in a climate chamber under a 12/12 h (lighting/dark) light protocol at 20 ° C and 65% relative humidity, and compound activity was assessed as untreated control leaves. When an appropriate level of disease damage occurs in the fragment (5-7 days after administration), disease control is compared to untreated. The following compounds produced at least 80% control of the nucleus: P12; P14; P01; P08; P09; P02; P15; P16; P17; P18; P19; P20; P22; P23; P25; P27; P30; P31; P32;P33;P34;P37;P38;P39;P40;P41;P42;P43;P44;P45;P47;P48;P49;P50;P51;P.53;P.54;P.58;P.59; P.61; P.62; P.66; P.67

Botrytis cinerea (Botryotinia fuckelian, Botrytis cinerea) / liquid culture (gray mold): Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (Vogels (Vogel) broth). After the DMSO solution of the test compound was placed in a 96-well microtiter plate at an application rate of 200 ppm, a nutrient broth containing fungal spores was added. The test plates were incubated at 24 ° C and the inhibition of growth was measured photometrically after 3-4 days of application. The following compounds produced at least 80% control of Botrytis cinerea: P12; P13; P14; P08; P09; P10; P07; P02; P03; P04; P15; P16; P17; P18; P19; P20; P21; P22; P23;P25;P26;P27;P28;P29;P30;P32;P33;P34;P35;P36;P37;P38;P39;P40;P41;P42;P43;P44;P45;P47;P48;P49;P50; P51; P.54; P.55; P.58; P.59; P.60; P.61; P.62; P.66;

Melon Glomerella bacteria (Glomerella lagenarium) (melons anthrax (lagenarium) Colletotrichum) / liquid culture (anthrax): Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (the PDB (potato dextrose broth)) in. After the DMSO solution of the test compound was placed in a 96-well microtiter plate at an application rate of 200 ppm, a nutrient broth containing fungal spores was added. The test plates were incubated at 24 ° C and the inhibition of growth was measured photometrically after 3-4 days of application. The following compounds produced at least 80% control of C. miniata: P14; P08; P09; P10; P07; P02; P04; P15; P16; P17; P18; P22; P24; P28; P29; P30; P32; P33 ;P36;P39;P40;P41;P42;P45;P47;P48;P49;P50;P51;P.53;P.54;P.55;P.58;P.59;P.61;P.62 ;P.66;P.67

Cercospora arachidicola / liquid culture (early leaf spot): Fungal conidia from frozen storage are directly mixed into nutrient broth (PDB (potato dextrose broth)). After the DMSO solution of the test compound was placed in a 96-well microtiter plate at an application rate of 200 ppm, a nutrient broth containing fungal spores was added. The test plates were incubated at 24 ° C and the inhibition of growth was determined photometrically after 4-5 days of application. The following compounds gave at least 80% control of peanut Leptosphaeria: P12; P01;; P14 P08 ; P09; P10; P03;; P07; P02 P04; P15; P16; P17; P18; P21; P22; P23; P24; P25;P26;P28;P29;P30;P32;P33;P34;P36;P37;P38;P39;P40;P41;P42;P43;P44;P45;P47;P48;P49;P51;P.53; 54; P.58; P.59; P.62; P.66; P.67

Mycosphaerella graminicola (Saccharomyces cerevisiae) / liquid culture (Septoria blotch): Mix fungal conidia from frozen storage directly into nutrient broth (PDB (potato dextrose broth)) in. After the DMSO solution of the test compound was placed in a 96-well microtiter plate at an application rate of 200 ppm, a nutrient broth containing fungal spores was added. The test plates were incubated at 24 ° C and the inhibition of growth was determined photometrically after 4-5 days of application. The following compounds were produced on Mycosphaerella graminicola at least 80% control of: P13; P01;; P14 P08 ; P06; P09; P02;; P10; P07 P03; P04; P15; P16; P17; P18; P19; P20; P21; P22;P23;P24;P25;P26;P27;P28;P29;P30;P32;P34;P36;P37;P38;P39;P40;P41;P42;P43;P44;P45;P47;P48;P49;P50; P51; P54; P62; P67

Gaeumannomyces graminis (Gaeumannomyces graminis) / liquid culture (all disease of cereals): filamentous fungi fragment from cryogenic storage were directly mixed into nutrient broth (the PDB (potato dextrose broth)) of. After the DMSO solution of the test compound was placed in a 96-well microtiter plate at an application rate of 200 ppm, nutrient broth CP33 containing fungal spores was added. The test plates were incubated at 24 ° C and the inhibition of growth was determined photometrically after 4-5 days of application. The following compounds produced at least 80% control of total pathogens of wheat: P12; P14; P08; P09; P10; P15; P17; P18; P19; P20; P21; P22; P23; P25; P27; P28; P29; P30; P31;P34;P36;P37;P38;P39;P40;P41;P42;P43;P44;P45;P48;P49 P51;P54;P55;P62;P67

Rhizoctonia solani (Limonium rhizogenes) / liquid culture (root rot, tripping disease): Mixing fresh growth liquid cultured fungal filament fragments directly into nutrient broth (PDB (potato dextrose broth)) in. After the DMSO solution of the test compounds was placed in a 96-well microtiter plate at an application rate of 200 ppm, a nutrient broth containing the fungal material was added. The test plates were incubated at 24 ° C and the inhibition of growth was determined photometrically after 3-4 days of application. The following compounds produced at least 80% control of Rhizoctonia solani : P14; P10; P07; P02; P03; P04; P15; P16; P17; P18; P21; P22; P25; P28; P30; P31; P32; P33 ;P34;P36;P37;P39;P40;P41;P42;P43;P44;P45;P47;P48;P49;P50;P51;P62;P67

Monographella nivalis ( C. oxysporum ) / liquid culture (cereal root rot): Mix fungal conidia from frozen storage directly into nutrient broth (PDB (potato dextrose broth)) . After the DMSO solution of the test compound was placed in a 96-well microtiter plate at an application rate of 200 ppm, a nutrient broth containing fungal spores was added. The test plates were incubated at 24 ° C and the inhibition of growth was determined photometrically after 4-5 days of application. The following compounds produced at least 80% control of Fusarium oxysporum : P12; P08; P10; P07; P02; P15; P16; P19; P23; P24; P25; P28; P29; P30; P32; P40; P41; P42 ;P43;P44;P45;P47;P48;P49;P50;P51;P59;P62;P66;P67

Wheat powdery mildew (Blumeria graminis f.sp. tritici, Erysiphe graminis f.sp. Tritici) / wheat / preventive leaf disc (wheat powdery mildew): Wheat cv Kanzler the blade section placed on agar in a 24-well plate, And sprayed with the formulated test compound diluted in water at an application rate of 200 ppm. After 1 day of application, the leaf discs were inoculated by shaking the powdery mildew infected plants on the test plates. Inoculated leaf discs were incubated in a climate chamber at 24 h dark followed by a 12/12 h (light/dark) light protocol at 20 ° C and 60% relative humidity, and compound activity was evaluated as Percentage of disease control compared to untreated when an appropriate level of disease damage occurred on treated leaf fragments (6-8 days after administration). The following compounds produced at least 80% control of wheat powdery mildew: P12; P14; P01; P08; P09; P07; P02; P03; P04; P15; P16; P17; P18; P19; P20; P22; P23; P27; P28 ;P30;P32;P33;P34;P37;P38;P39;P40;P41;P42;P44;P45;P47;P48;P49;P50;P51;P54;P59;P60;P61;P62;P66;P67

Ultimate Pythium /Liquid Culture (Planting Disease): The fresh growth liquid cultured fungal filamentous fragments and oospores are directly mixed into the nutrient broth (potato dextrose broth). After the DMSO solution of the test compound was placed in a 96-well microtiter plate at an application rate of 200 ppm, a nutrient broth containing a fungal filament/spore mixture was added. The test plates were incubated at 24 ° C and the inhibition of growth was determined photometrically after 2-3 days of application. The following compounds produced at least 80% control of Pythium ultimum: P13; P14; P08; P09; P02; P03; P04; P15; P16; P18; P20; P22; P24; P31; P33; P39; P40; P41; P44 ; P45; P47; P48; P49; P50; P60; P61

Magnaporthe grisea (Rice Pear) / Rice / Leaf Disc Prevention (Rice Blast): Place the rice leaf fragment of cv Ballila on agar in a multiwell plate (24-well format) at 200 ppm The application rate was sprayed with the formulated test compound diluted in water. After 2 days of application, the leaf fragments were inoculated with a spore suspension of the fungus. The inoculated leaf fragments were incubated in a climatic chamber under a light regime of 24 h dark followed by 12/12 h (lighting/dark) at 22 ° C and 80% relative humidity, and the compound activity was evaluated as Percentage of disease control compared to untreated when an appropriate level of disease damage occurred in the untreated control leaf fragments (5-7 days after administration). The following compounds produced at least 80% control of gray large shells: P14; P08; P09; P07; P02; P03; P04; P15; P16; P18; P19; P20; P22; P23; P30; P32; P33; P38; P39;P40;P41;P42;P43;P45;P51;P53;P54;P60;P61;P62;P66;P67;P68

Alternaria solani / tomato / leaf disc (early blight): Place tomato leaf disc cv.Baby on agar in a multiwell plate (24-well format) and prepare with dilution in water Test compound spray. After 2 days of application, the leaf discs were inoculated with a spore suspension of the fungus. Inoculated leaf discs were incubated at 23 ° C / 21 ° C (day/liquid night) and 80% rh in a climatic chamber under a 12/12 h (light/dark) light protocol and compound activity was evaluated as Percentage of disease control compared to untreated when an appropriate level of disease damage occurred in the untreated control leaf fragments (5-7 days after administration). The following compounds produced at least 80% control of Alternaria solani at an application rate of 200 ppm or less: P07; P02; P15; P38; P40

Claims (17)

A method comprising applying a compound of formula (I) to a useful plant, a locus thereof or a propagation material thereof Wherein L ¹ is N or CD ¹ ; L ² is N or CD ² ; L ³ is N or CD ³ ; L ⁴ is N or CD ⁴ ; L ⁵ is N or CD ⁵ ; L ⁶ is N or CD ⁶ ; ¹ , D ² , D ³ , D ⁴ , D ⁵ and D ⁶ independently of each other 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 from one to four heteroatoms independently selected from O, S and N (provided that the heterocycle does not contain a contiguous Oxygen atom, adjacent sulfur atom or adjacent sulfur and oxygen atom), COR ¹ , OR ² , SH, C ₁ -C ₈ alkylthio group, C ₁ -C ₈ alkylsulfinyl group, C ₁ -C _8- alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, N(R ³ ) ₂ , CO ₂ R ² , O(CO)R ¹ , CON(R ³ ) ₂ , NR ³ COR ¹ , CR ¹ N-OR ² , wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, and heterocyclic ring are optionally independently selected from halo, CN, NH by one or more ^{_{2, NO 2, oR 2,}} C 1 -C 4 alkyl and C ₁ -C ₄ haloalkyl groups; or D ¹ and D ^5, D ² and D ^5, D ³ and D ^6, D ^4, or and D ⁶ are each independently, together with their attached thereto sheet May be formed partially or fully unsaturated 5- to 7-membered carbocyclic or partially or fully unsaturated, containing from one to three substituents independently selected from O, S, N and N (R ³⁾ hetero atoms, a 5- to a 7-membered heterocyclic ring, provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms, and wherein D ¹ and D ⁵ , D ² and D ⁵ , D ³ and D The ring formed by ⁶ , or D ⁴ and D ⁶ may optionally be selected from one or more independently selected from the group consisting of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkane. a group substituted with a C ₁ -C ₄ alkoxy group and a C ₁ -C ₄ haloalkoxy group; X represents X-2, X-3, X-4 or X-5: 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 independently of each other represent CR ⁴ R ⁵ , C=O or C= CR ⁶ R ⁷ ; Z ⁴ and Z ¹² represent CR ⁸ R ⁹ , SiR ¹⁰ R ¹¹ , C=O or C=CR ⁶ R ⁷ ; wherein the combinations X-2, X-3, X-4 and X- 5 contain at most one ring, which comprises only Z ¹ to Z ¹⁴ group comprises one or two Z ¹ to Z ¹⁴ radicals comprising three or Z ¹ to Z ¹⁴ or a group Z ¹ comprises Four of the Z ¹⁴ groups are ring members; 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 do not represent a carbon atom substituted by two OH; the Q group is selected from the group consisting of Q-1, Q-2, Q-3, Q-4, Q. -5, Q-6, Q-7, Q-8, and Q-9 Y ¹ , Y ² , Y ³ and Y ⁴ each independently represent hydrogen, halogen, CN, NO ₂ , C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₂ -C ₈ alkenyl, a C ₂ -C ₈ alkynyl group, a benzyl group, a phenyl group, a 5- or 6-membered heterocyclic ring containing one to three hetero atoms independently selected from O, S and N (provided that the heterocyclic ring does not contain contiguous An oxygen atom, an adjacent sulfur atom or an adjacent sulfur and oxygen atom), COR ¹ , OR ² , SH, a C ₁ -C ₈ alkylthio group, a C ₁ -C ₈ alkylsulfinyl group, a C ₁ -C _{8 group} Alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, N(R ³ ) ₂ , CO ₂ R ² , O(CO)R ¹ , CON(R ³ ) ₂ , NR ³ COR ¹ , CR ¹ N-OR ² , wherein the alkyl, cycloalkyl, alkenyl, alkynyl, benzyl, phenyl, and heterocyclic ring are optionally independently selected from halo, CN by one or more a group substituted with NH ₂ , NO ₂ , OR ² , C ₁ -C ₄ alkyl and C ₁ -C ₄ haloalkyl; when Q systems Q-1, Q-2, Q-3, Q-4, Q -6 or Q-7, Y ¹ and Y ² , Y ² and Y ³ , or Y ³ and Y ⁴ independently of each other together with the fragments to which they are attached may form partially or fully unsaturated 5- to 7 - meta carbon ring or partial or not at all a 5- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, N and N(R ³ ), provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur An atom or a contiguous sulfur and oxygen atom, and wherein the ring formed by Y ¹ and Y ² , Y ² and Y ³ , or Y ³ and Y ⁴ is optionally independently selected from halogen, CN, by one or more 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 Substituted; when Q is Q-1, Q-3, Q-4, Q-7 or Q-8 and L ¹ is CD ¹ , then Y ¹ and D ¹ together with the fragments 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- or one containing two heteroatoms independently selected from O, S, N and N(R ³ ) To a 7-membered heterocyclic ring, provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms, and wherein the ring formed by D ¹ and Y ¹ may optionally be subjected to one or A plurality of independently selected from the group consisting of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C _a group substituted with ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ alkylthio; when Q is Q-9 and L ¹ is CD ¹ , then R ¹² and D ¹ Together, it may be -(G ¹ ) _p -G ² -G ³ -; Q' is selected from the group consisting of Q-1', Q-2', Q-3', Q- 4', Q-5', Q-6', Q-7', Q-8' and Q-9' Y ^{1 '} , Y ^{2 '} , Y ^{3 '} and Y ^{4 '} each independently 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, benzyl, phenyl, 5- or 6-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S and N (conditions are: heterozygous The ring does not contain adjacent oxygen atoms, adjacent sulfur atoms or adjacent sulfur and oxygen atoms), COR ¹ , OR ² , SH, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfinylene, C ₁ -C ₈ alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, N(R ³ ) ₂ , CO ₂ R ² , O(CO)R ¹ , CON(R ³ ) ₂ , NR ³ COR ¹ , CR ¹ N-OR ² , wherein the alkyl, cycloalkyl, alkenyl, alkynyl, benzyl, phenyl and heterocyclic ring may optionally be independently or in one or more a group substituted with halogen, CN, NH ₂ , NO ₂ , OR ² , C ₁ -C ₄ alkyl, and C ₁ -C ₄ haloalkyl; when Q' is Q-1', Q-2', Q -3', Q-4', Q-6' or Q-7', Y ^{1 '} and Y ^2' , Y ^2' and Y ^3' , or Y ^3' and Y ^4' are independently of each other The fragment attached thereto can form a partially or fully unsaturated 5- to 7-membered carbocyclic ring. Partially or fully unsaturated, containing from one to three substituents independently selected from 5- to 7-membered heterocyclic ring O, S, N and N (R ³⁾ hetero atoms, with the proviso that the heterocyclic ring does not contain a line adjacent to an oxygen atom a contiguous sulfur atom or an adjacent sulfur and oxygen atom, and wherein the ring formed by Y ^{1 '} and Y ^{2 '} , Y ^{2 '} and Y ^{3 '} , or Y ^{3 '} and Y ^{4 '} may optionally be subjected to one or A plurality of independently 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, C ₁ -C ₄ haloalkoxy a group substituted with a C ₁ -C ₄ alkylthio group; when Q' is Q-1', Q-3', Q-4', Q-7' or Q-8' and L ⁴ is CD ⁴ And Y ^{1 '} and D ⁴ together with the fragments to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or partially or fully unsaturated, containing one or two independently selected from a 5- to 7-membered heterocyclic ring of a hetero atom of O, S, N and N(R ³ ), provided that the heterocyclic ring does not contain an adjacent oxygen atom, an adjacent sulfur atom or an adjacent sulfur and oxygen atom, and The ring formed by D ⁴ and Y ^{1 '} may optionally be selected from one or more independently selected from the group consisting of halogen, CN, NH ₂ , NO ₂ , OH, C ₁ -C Substituted by a group of ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ alkylthio; when Q' is Q-9 'And L ⁴ is CD ⁴ , then R ^{12 '} and D ⁴ may together be -(G ¹ ) _p -G ² -G ³ -; each G ¹ and G ² independently of each other represents -C(R ¹⁴ R ¹⁵ )-; each G ³ independently of each other represents -C(R ¹⁴ R ¹⁵ )-, O, N(R ¹⁶ ) or S; or each combination G ¹ and G ² , or G ² and G ³ , or G ¹ and G ¹ together represent each other independently -CR ¹⁴ =CR ¹⁵ -; each p independently of each other represents 0, 1 or 2; each R ¹ independently of ^one another 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 the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl And benzyl and pyridyl are optionally independently selected from halo, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ - Substituted by a C ₄ alkoxy group and a C ₁ -C ₄ haloalkoxy group; each R ² independently of one another represents hydrogen, C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkynyl, phenyl, benzyl or one a 5- or 6-membered heterocyclic ring 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, cycloalkyl, alkenyl, alkynyl, phenyl, benzyl and heterocyclic ring are optionally independently selected from halo, CN, NH ₂ , NO ₂ , OH, C ₁ via one or more -C ₄ alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkane Substituted by a group; each R ³ independently of one another 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 ¹ , wherein the alkyl, alkoxy, alkenyl and alkynyl groups are optionally substituted by one or more halogens; When two groups R ³ are attached to the same nitrogen atom, the groups may be the same or different; wherein when the two groups R ³ are attached to the same nitrogen atom, the two groups can not be OH, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy group; and wherein when two groups R ³ are attached to the relative In the case of a 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: Wherein the ring formed may optionally be selected from one or more independently 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 and C ₁ -C ₄ haloalkoxy groups are substituted; R ⁴ and R ⁵ each independently represent hydrogen, halogen, CN, OH, SH, CHO, C ₁ -C ₆ alkyl, C ₂ - C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ alkynyloxy, C ₁ -C ₆ alkylthio, C _1- C ₆ alkoxycarbonyl, C ₃ -C ₆ cycloalkyl, CON(R ³ ) ₂ , NH ₂ , NR ³ COR ¹ , CR ¹ N-OR ² , phenyl or one to four independently selected a 5- or 6-membered heterocyclic ring of a hetero atom of 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 alkene The base, alkynyl, phenyl and heterocyclic ring may be optionally independently selected from halo, OH, OR ² , CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, CON(R ³ ) ₂ , NH ₂ , NR ³ COR ¹ and benzene Base group Generation; or R ⁴ and R ⁵ together with the carbon atoms they are attached to form thereon a C ₃ -C ₆ cycloalkyl group or halogenated C ₃ -C ₆ cycloalkyl group together; each R ⁶ and R ⁷ independently of each other represents hydrogen, halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl; R ⁸ and R ⁹ each independently represent hydrogen, halogen, CN, OH, SH, CHO, C ₁ - C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ alkoxy, C ₃ -C ₆ alkenyloxy, C ₃ -C ₆ alkynyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkoxycarbonyl, C ₃ -C ₆ cycloalkyl, CON(R ³ ) ₂ , NH ₂ , NR ³ COR ¹ , CR ¹ N-OR ² , phenyl Or a 5- or 6-membered heterocyclic ring containing one to four heteroatoms independently selected from O, S and N, provided that the heterocyclic ring does not contain contiguous oxygen atoms, adjacent sulfur atoms or adjacent sulfur and oxygen An atom wherein the alkyl, alkenyl, alkynyl, phenyl and heterocyclic ring are optionally independently selected from one or more of the group consisting of halogen, OH, OR ² , CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, CON(R ³ ) ₂ , NH ₂ , NR ³ COR ¹ and a group of a phenyl group are substituted; or R ⁸ and R ⁹ together with the carbon atom to which they are attached form a C ₃ -C ₆ cycloalkyl group or a C ₃ -C ₆ halocycloalkyl group R ¹⁰ and R ¹¹ each independently represent hydrogen, halogen, CN, OH, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkane Oxyl, C ₂ -C ₄ alkenyloxy or phenyl, wherein phenyl is optionally independently selected from halo, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl via one or more a group substituted with a C ₁ -C ₄ alkoxy group and a C ₁ -C ₄ haloalkoxy group; R ¹² and R ^{12 '} independently of each other represent hydrogen, halogen, CN, SH, C ₁ -C ₈ alkylthio group, 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 ² O)carbonyl (C ₁ -C ₄ alkyl), phenyl or pyridyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, phenyl and pyridine The group may be optionally selected from one or more independently selected from the group consisting of halogen, CN, NH ₂ , NH-C ₁ -C ₈ alkyl, N(C ₁ -C ₈ alkyl) ₂ , NO ₂ , OR ² , C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkoxy , C ₃ -C ₆ cycloalkyl group and containing one to three groups independently selected from 5- or 6-membered heterocyclic O, S and N, heteroatom substituted, with the proviso system: the heterocyclic ring does not contain adjacent Oxygen atom, adjacent sulfur atom or adjacent sulfur and oxygen atom; R ¹³ and R ^13' independently of each other represent hydrogen, C ₁ -C ₈ alkyl, C ₃ -C ₈ cycloalkyl, C ₃ -C ₈ An alkenyl group, a C ₃ -C ₈ alkynyl group, a phenyl group, a benzyl group or a pyridyl group, wherein the alkyl group, cycloalkyl group, alkenyl group, alkynyl group, phenyl group, benzyl group and pyridyl group are optionally subjected to one or A plurality of independently 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, and C ₁ -C ₄ haloalkoxy Substituted by a group; R ¹⁴ and R ¹⁵ each independently represent hydrogen, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ Haloalkoxy; each R ¹⁶ independently of one another represents hydrogen, OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₆ cycloalkyl, C ₁ -C ₈ alkylcarbonyl Or a C ₁ -C ₈ haloalkylcarbonyl group; or a salt or N oxide thereof. The method of claim 1, wherein X is X-3. The method of claim 1 or 2, wherein Q is Q1, Q2, Q-3 or Q9 and Q' is Q1', Q2', Q-3' or Q9'. The method of any one of claims 1 to 3, wherein L ¹ is CD ¹ , L ² is CD ² , and L ⁵ is CD ⁵ . The method of any one of claims 1 to 4, wherein L ¹ is CD ¹ , L ² is CD ² , L ³ is CD ³ , L ⁴ is CD ⁴ , L ⁵ is CD ⁵ and L ⁶ series CD ⁶ . The method of any one of claims 1 to 3, wherein L ¹ is CD ¹ , L ² is N, and L ⁵ is CD ⁵ . The method of any one of claims 1 to 3, wherein L ¹ is CD ¹ , L ² and L ³ is N, L ⁴ is CD ⁴ , L ⁵ is CD ⁵ and L ⁶ is CD ⁶ . The method of any one of claims 1 to 3, wherein L ¹ is N, L ² is CD ² , and L ⁵ is CD ⁵ . The method of any one of claims 1 to 3, wherein L ¹ and L ⁴ are N, L ² is CD ² , L ³ is CD ³ , L ⁵ is CD ⁵ and L ⁶ is CD ⁶ . The method of any one of claims 1 to 9, wherein L ¹ is the same as L ⁴ , L ⁵ is the same as L ⁶ , L ² is the same as L ³ , and Q is the same as Q′. The method of any one of claims 1 to 10, wherein D ¹ , D ² , D ³ , D ⁴ , D ⁵ , D ⁶ , Y ¹ , Y ² , Y ³ , Y ⁴ , Y ^1' , Y ^{2 '} , Y ^3' and Y ^4' independently of each other represent hydrogen, halogen, C ₁ -C ₈ alkyl, C ₂ -C ₈ alkynyl, C ₁ -C ₈ alkoxy or C ₁ - C ₈ alkylthio group. The method of any one of claims 1 to 11, wherein R ¹³ and R ^{13 '} independently of each other represent hydrogen, C ₁ -C ₄ alkyl, C ₃ -C ₆ alkenyl, C ₃ - C ₆ alkynyl or benzyl, wherein the alkyl, alkenyl, alkynyl and benzyl are optionally substituted by one or more groups, for example one to five groups, which are independently selected from C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, halogen, CN, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkoxy. The method of any one of claims 1 to 12, wherein the method is a method of controlling or preventing a disease caused by a plant pathogen on a useful plant or a propagation material thereof. A compound of formula I as defined in any one of claims 1 to 12, wherein X is X-3, X-4 or X-5 and the compound of formula I is not of formula I' Compound Wherein R ^a is hydrogen or phenyl, R ^b is a primary alkyl group and n is 4 or 5; and the compound of formula I is not a compound of formula I" Wherein each R ^{c is} independently hydrogen or methyl; and the compound of formula I is not a compound of formula I'''a, I'''b or I'''c And the compound of formula I is not a compound of formula I''' Wherein n is 3, R ^d and R ^e are all methyl, R ^f and R ^g are all hydrogen; or n is 3, R ^d and R ^e R ^f and R ^g are all hydrogen; or n is 4, R ^d And R ^e is hydrogen, R ^f and R ^g are all hydrogen; or n is 4, R ^d and R ^e are all p-methylphenyl, R ^f and Rg are hydrogen; or n is 4, R ^d and R ^e are And R ^f and R ^g are both hydrogen; or n is 4, R ^d and R ^e are both n-butyl, R ^f and R ^g are all hydrogen; or n is 4, R ^d and R ^e are all hydrogen, R ^f and R ^g are all hydrogen; or n is 4, R ^d and R ^e are all p-hydroxyphenyl, R ^f and R ^g are all hydrogen; or n is 4, R ^d and R ^e R ^f and R ^g are both Is hydrogen; or n is 5, R ^d and R ^e are all n-butyl, R ^f and R ^g are all hydrogen; or n is 4, R ^d and R ^e are all hydrogen, and R ^f and R ^g are both Methoxyphenyl. A compound of formula I as described in claim 14, wherein when Q is Q-3, Q-4, Q-7 or Q-8 and L ¹ is CD ¹ and Q is not Q-1, then Y ¹ and D ¹ together with the fragments to which they are attached may form a partially or fully unsaturated 5- to 7-membered carbocyclic ring or partially or fully unsaturated, containing one to three independently selected from O, S, a 5- to 7-membered heterocyclic ring of N and N(R ³ ₎ heteroatoms, provided that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms, and wherein D ¹ Rings formed with Y ¹ may optionally be independently selected from halo, CN, NH ₂ , NO ₂ , OH, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ - Substituted by a C ₄ alkoxy group, a C ₁ -C ₄ haloalkoxy group; R ⁸ represents hydrogen, halogen, CN, OH, SH, CHO, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkenyl, C ₁ -C ₆ alkynyl, C ₁ -C ₆ alkoxy, C _{1 -C6} alkenyloxy, C ₁ -C ₆ alkynyloxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ haloalkylthio a C ₃ -C ₆ cycloalkyl group, a phenyl group or a 5- or 6-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S and N, the conditions of which are The heterocyclic ring does not comprise contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms, wherein the alkyl, alkenyl, alkynyl, phenyl and heterocyclic rings are optionally independently selected by one or more From halogen, OH, CN, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, and Substituted with a C ₁ -C ₄ haloalkylthio group; when Q is Q-1, Y ⁴ represents 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, COR ¹ , OR ² , SH, C ₁ -C ₈ alkylthio, C ₁ -C ₈ alkylsulfinylene, C ₁ -C ₈ alkylsulfonyl, phenylthio, phenylsulfinyl, phenylsulfonyl, N(R ³ ) ₂ , CO ₂ R ² , O(CO)R ¹ , CON(R ³ ) ₂ , NR ³ COR ¹ , CR ¹ N-OR ² , wherein the alkyl, cycloalkyl, alkenyl, alkynyl, and phenyl groups are optionally independently selected from halo, CN, NH by one or more ^{_{2, NO 2, oR 2,}} C 1 -C 4 alkyl, substituted C ₁ -C ₄ haloalkoxy and C ₁ -C ₄ alkylthio groups; or together with Y ³ and Y ⁴ together with their attached thereon to Fragment can be shaped Partially or fully unsaturated 5- to 7-membered carbocyclic or partially or fully unsaturated, 5- to 7 comprising one to three independently selected from O, S, N and N (R ³⁾ heteroatoms a heterocyclic ring, the condition being such that the heterocyclic ring does not contain contiguous oxygen atoms, contiguous sulfur atoms or contiguous sulfur and oxygen atoms, and wherein the ring formed by Y ³ and Y ⁴ may optionally be separated by one or more a group 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, and C ₁ -C ₄ haloalkoxy Replaced by the regiment. a compound having the chemical formula Int-1 Wherein X' represents -CH=CH-CH ₂ - or CH ₂ -CH=CH- and Q, Q ' , L ¹ , L ² , L ³ , L ⁴ , L ⁵ and L ⁶ are as claimed in the patent application a compound of the formula (I) as defined in any one of items 1 to 13, or a salt or N-oxide thereof; or a compound having the chemical formula Int-2 Wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ and X are as defined for the compound of formula (I) as defined in any one of claims 1 to 13 of the patent application, or Salt or N-oxide; compound having the chemical formula Int-3 Wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Q and X are as defined for the compound of formula (I) as defined in any one of claims 1 to 13 of the patent application, Or a salt or N-oxide thereof; a compound having the chemical formula Int-4 Wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Q and X are as defined for the compound of formula (I) as defined in any one of claims 1 to 13 of the patent application, Or a salt thereof or an N-oxide; a compound having the chemical formula Int-5 Wherein L ¹ , L ² , L ³ , L ⁴ , L ⁵ , L ⁶ , Q and X are as defined for the compound of formula (I) as set forth in any one of claims 1 to 13 and The R ²⁸ halogen is specifically chlorine, bromine or iodine, or a salt or N-oxide thereof. A composition comprising a fungicidally effective amount of a compound of formula (I) as defined in any one of claims 1 to 15 of the patent application, optionally comprising at least one additional active ingredient.