TW201332947A - Pesticidal compounds - Google Patents

Abstract

A compound of formula (I) wherein R1 to R4 are, for example, each hydrogen, R5 is, for example, a substituted phenol; R6 is, for example, hydrogen; R7 is, for example, hydrogen, cyano, hydroxyl, formyl, C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, or C2-C4-alkynyl; and A1 to A5 is, for example, A1 is N or C-X, A3 is C-X, and A2, A4 and A5 are C-H, where X, is, for example, halogen; and its use as a pesticidal agent.

Description

Pesticide-killing compound

The present invention relates to certain N-[1-(2-phenyl)cyclopropylmethyl]heteroarylcarboxamide derivatives, to processes for their preparation, to compositions comprising the compounds, and to It relates to its use in the fields of agriculture and veterinary medicine and in the field of pest management. These compounds are particularly effective in controlling pests in agriculture as well as damage to plants by fungal diseases.

The inventors have discovered that certain N-[1-(2-phenyl)cyclopropylmethyl]heteroarylcarboxamide derivatives are responsible for controlling damage caused by pest & fungal diseases, particularly nematode pests. It is especially effective.

Accordingly, the present invention relates to a compound of formula (I) having a compound of formula (I), wherein Wherein R 1 is hydrogen, methyl or halogen; R 2 is hydrogen, methyl or halogen; R 3 is hydrogen, methyl or halogen; R 4 is hydrogen, methyl or halogen; R 5 is substituted or unsubstituted phenyl; R6 is hydrogen or C ₁ -C ₄ -alkyl; R7 is hydrogen, cyano, hydroxy, decyl, C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2- C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-cyanoalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, benzyl, C3 -C6-cycloalkylcarbonyl or C3-C6-cycloalkoxycarbonyl; A1 is N, CH or CX; A2 is N, CH or CX; A3 is N, CH or CX; A4 is N, CH or CX; A5 is N, CH or CX; the conditions are wherein A1 & A5 are each N, then A2 to A4 are independently selected from CH, CX and N; or wherein A2 is CX, then A1, A3 to A5 are independently selected from CH, N or CX; or wherein A1 is CX and A5 is N, then A2 to A4 are independently selected from CX and CH; or wherein A1 is CX and A5 is CH, then one of A2 to A4 is CX and the rest Each line CH; or wherein A1 is CX and A4 is N, then A2, A3 and A5 are independently selected from CX and CH; X-type halogen , OH, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; conditions of at most three of A1 to A5 N; together with acceptable salts, enantiomers, diastereomers, tautomers and N-oxides.

The compounds of the formula (I), in each case in free form or in the form of a salt, and optionally the tautomer thereof, may be present in the form of one of the possible isomers or as such a mixture, for example purely a form of an isomer, such as an enantiomer and/or a diastereomer, or as a mixture of isomers, such as a mixture of enantiomers, such as a racemate, a mixture of diastereomers or Racemic mixture, depending on the number, absolute and relative configuration of asymmetric carbon atoms present in the molecule, and/or depending on the configuration of non-aromatic double bonds present in the molecule; the present invention relates to such Pure isomers, and also to all possible mixtures of isomers and in the present case and in the following each case (even if the details of stereochemistry are not specifically mentioned in each case) should be understood in this sense . Accordingly, 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. As an example, the compounds of the invention may, for example, contain one or more asymmetric carbon atoms at the -CR ⁶ -, -CR ⁵ -, -CR ¹ R ² -, and -CR ³ R ⁴ - groups, and have the formula ( The compounds of I) may exist as enantiomers (or diastereomeric pairs) or as a mixture of such.

The invention also encompasses salts or N-oxides of each of the compounds of formula (I).

Those skilled in the art will also appreciate that since the salt of a chemical compound is in equilibrium with its corresponding non-salt form in the environment and under physiological conditions, the salt also has a biological effect in a non-salt form.

Thus, various salts of the compounds of the invention (and the active ingredients used in combination with the active ingredients of the invention) are useful for controlling invertebrate pests and animal parasites. Salts in agriculturally and/or physiologically acceptable salts include acid addition salts with inorganic or organic acids such as hydrobromic acid, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, acetic acid, butyric acid, fumaric acid. , lactic acid, maleic acid, C Diacid, oxalic acid, propionic acid, salicylic acid, tartaric acid, 4-toluenesulfonic acid or valeric acid.

Suitable salts in agriculturally and/or physiologically acceptable salts may also be those which do not adversely affect the pesticidal and/or parasiticidal action of the compounds of formula (I). Therefore, particularly suitable ions of the alkali metal (including sodium, potassium and lithium), ions of alkaline earth metals (including calcium and magnesium), and transition metals (including manganese, copper, iron, zinc, cobalt, lead, silver, Nickel) ions, as well as ammonium or organic ammonium (including monoalkylammonium, dialkylammonium, trialkylammonium, tetraalkylammonium, monoalkenylammonium, dienylammonium, triallyl ammonium, monoalkyne Alkyl ammonium, di-alkynyl ammonium, monoalkanol ammonium, ammonium dialkanol, C5-C6-cycloalkylammonium, piperidinium, An ion of oxonium, pyrrolidinium or benzylammonium, in addition to cerium ions, cerium ions, preferably tris(C1-C4-alkyl)anthracene and sulfoxonium ions, preferably three (C1-C4-alkyl) ruthenium oxide.

Alkyl group (either alone or as part of a larger group, such as alkoxy-, alkylsulfanyl-, alkylsulfinyl-, alkylsulfonyl-, alkyl The carbonyl- or alkoxycarbonyl-) may be in a straight or branched form and is, for example, methyl, ethyl, propyl, propan-2-yl, butyl, butan-2-yl or 2-methyl- Prop-2-yl. In each embodiment of the invention, an alkyl group (alone or as part of a larger group, such as alkoxy-, alkylsulfanyl-, alkylsulfinyl-, alkyl) The sulfonyl-, alkylcarbonyl- or alkoxycarbonyl-) is preferably a C1-C3-alkyl group, more preferably a C1-C2-alkyl group, especially a methyl group. In the case of alkoxy groups, the examples are methoxy, ethoxy, propoxy, n-butoxy, isobutoxy, and their isomeric groups; preferably, independently of the others The embodiments are methoxy and ethoxy, especially methoxy.

The alkenyl group may be in the form of a straight chain or a branched chain, and may be an (E)- or (Z)-configuration as appropriate. Examples are vinyl and allyl groups. In each of the embodiments of the present invention, the alkenyl group is preferably a C2-C3-alkenyl group, more preferably a vinyl group and an allyl group.

The alkynyl group can be in the form of a straight chain or a branched chain. Examples are ethynyl and propargyl groups. In each embodiment of the invention, the alkynyl group is preferably a C2-C3-alkynyl group, more preferably a propargyl group.

Halogen is fluorine, chlorine, bromine or iodine; in each embodiment of the invention, the halogen is fluorine, chlorine or bromine; especially fluorine or chlorine.

Haloalkyl groups (alone or as part of a larger group, such as haloalkoxy-, haloalkylsulfanyl-, haloalkylsulfinyl- or haloalkylsulfonyl-) An alkyl group substituted by one or more of the same or different halogen atoms and is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl and 2,2,2-trifluoroethyl . In each embodiment of the invention, a haloalkyl group (either alone or as part of a larger group, such as haloalkoxy-, haloalkylsulfanyl-, haloalkylsulfinyl)- Or haloalkylsulfonyl-), haloalkyl is preferably trifluoromethyl. In the case of a haloalkoxy group, examples are fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetra. Fluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy; preferably difluoromethoxy 2,2,2-Trifluoroethoxy, 2-chloroethoxy and trifluoromethoxy.

The cycloalkyl group is monocyclic and is, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. In each embodiment of the invention, the C3-C6-cycloalkyl group is preferably a C3-C5-cycloalkyl group, more preferably a C3-C4-cycloalkyl group, especially a C3-ring. Alkyl group. When a cycloalkyl moiety is referred to as being substituted, the cycloalkyl moiety is preferably substituted with from one to four substituents, most preferably from one to three substituents, such as one or two substituents, especially A substituent.

Alkoxycarbonyl, such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, secondary butoxycarbonyl, and tertiary butyl Oxycarbonyl; preferred are methoxycarbonyl, ethoxycarbonyl and isopropoxycarbonyl.

An alkylsulfanyl group, for example, methylsulfanyl, ethylsulfanyl, propylsulfanyl, isopropylsulfanyl, n-butylsulfanyl, isobutylsulfanyl, A secondary butyl sulfanyl group and a tertiary butyl sulfanyl group. Examples of haloalkylsulfanyl groups are chloro- and/or fluoro-halogenated substituents such as difluoromethylsulfanyl, trifluoromethylsulfanyl, chlorodifluoromethylsulfanyl and 2,2,2-Trifluoro-ethylsulfanyl.

Alkylsulfinyl, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutyl Sulfosyl, secondary butyl sulfinylene, and tertiary butyl sulfinylene. Examples of haloalkylsulfinyl groups are chlorine- and/or fluorine-halogenated substituents such as difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethyl Sulfosyl and 2,2,2-trifluoro-ethylsulfinyl.

An alkylsulfonyl group, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, A secondary butyl sulfonyl group and a tertiary butyl sulfonyl group. Examples of haloalkylsulfonyl are chloro- and/or fluoro-halogenated substituents such as difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl and 2,2,2-Trifluoro-ethylsulfonyl.

Alkoxyalkyl, for example, methoxymethyl, 2-methoxyethyl, ethoxymethyl, 2-ethoxyethyl, n-propoxymethyl, 2-n-propoxy Ethyl, isopropoxymethyl and 1-isopropoxyethyl. In each embodiment of the invention, the alkoxyalkyl group is preferably a C1-C4-alkoxy-C1-C4-alkyl group, more preferably a C1-C2-alkoxy-methyl group. Such as methoxymethyl and ethoxymethyl groups.

The aryl groups (alone or as part of a larger group, such as aryl-alkylene-) are aromatic ring systems which may be mono-, di- or tricyclic. Examples of such rings include phenyl, naphthyl, Mercapto, fluorenyl or phenanthryl. Preferred aryl groups are phenyl and naphthyl, and phenyl is most preferred.

Examples of cycloalkylcarbonyl groups are cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl and cyclohexylcarbonyl; preferred are cyclopropylcarbonyl and cyclobutylcarbonyl.

Examples of cycloalkoxycarbonyl groups are cyclopropoxycarbonyl, cyclobutoxycarbonyl, cyclopentyloxycarbonyl and cyclohexyloxycarbonyl; preferred are cyclopropoxycarbonyl and cyclobutoxycarbonyl.

In an embodiment, independent of other embodiments, at least two hydrogens of R1, R2, R3 and R4 of the compound of formula (I); preferably at least three; especially R1, R2, R3 and R4 is each hydrogen.

In an embodiment, at least one, preferably one halogen or methyl group, of R1, R2, R3 and R4 having the compound of formula (I), independently of the other embodiments.

In an embodiment, independent of other embodiments, R5 is an unsubstituted phenyl group.

In an embodiment, independent of other embodiments, R5 is a substituted phenyl group having from 1 to 5 substituents.

In an embodiment, independently of other embodiments, R5 is a substituted phenyl group having from 1 to 3 substituents.

In an embodiment, independent of other embodiments, R5 is a substituted phenyl group having two substituents.

In an embodiment, independent of other embodiments, R5 is a substituted phenyl group having one substituent.

In embodiments, independent of other embodiments, if R5 is a substituted phenyl group, the or the substituents are independently selected from the group consisting of halogen, cyano, C1-C4-alkyl, C1-C4-halane. , C1-C4-alkoxy, C1-C4-halooxy, C1-C4-alkylsulfanyl, C1-C4-haloalkylsulfanyl, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, C3-C6-cycloalkane The cycloalkyl group is unsubstituted or substituted with one or more substituents Rx, wherein Rx, independently of one another, is selected from the group consisting of halogen, C1-C4-alkyl, and C1-C4-haloalkyl.

In embodiments, independent of other embodiments, if R5 is a substituted phenyl group, this or the substituents are independently selected from the group consisting of halogen, C1-C4-alkyl, and C1-C4-haloalkyl.

In an embodiment, R5 is cyano substituted phenyl (the phenyl group may be optionally further substituted by halogen or trifluoromethyl), 2-fluoro-4-trifluoromethylphenyl, 2,6- Difluoro-4-chloro-phenyl, 2,4-difluorophenyl, 2,4,6-trifluorophenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-4-bromophenyl, 2-chloro-4-fluorophenyl, 2-chloro-4-trifluoromethylphenyl, 3,4,5-trifluorophenyl, 2,4-dichloro-6-fluorophenyl, 2,4 - Dibromophenyl or 2,4-dichlorophenyl, wherein in each case, phenyl represents phenyl-1-yl.

In an embodiment, independent of other embodiments, R5 is any one of the R5 substituents described in Table P below.

In an embodiment, independent of other embodiments, R6 is hydrogen or C1-C2 alkyl, preferably hydrogen or methyl.

In an embodiment, independent of other embodiments, R7 is selected from the group consisting of hydrogen, cyano, hydroxy, decyl, C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2- C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, and benzyl. Preferably, R7 is hydrogen, hydroxy, C1-C2-alkyl, C1-C2-alkoxy, C2-alkenyl, C3-alkynyl, C1-C2-alkoxy-C1-alkyl, C1 -C2-alkylcarbonyl and C1-C2-alkoxycarbonyl, especially hydrogen, hydroxy, methyl, cyano, methionyl, methoxy, allyl, propargyl, methoxycarbonyl, A Oxymethyl and benzyl; in particular, R7 is hydrogen.

In a preferred group of compounds of formula (I), R1 to R4 are each hydrogen; R5 is substituted or unsubstituted phenyl; R6 is hydrogen or C1-C4-alkyl; R7 is hydrogen , C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl; and A1 & A5 are each N, then A2 to A4 are independently selected from CH, CX and N; or A2 is CX, then A1 A3 to A5 are independently selected from CH, N or CX; or A1 is CX and A5 is N, then A2 to A4 are independently selected from CX and CH; or A1 is CX and A5 is CH, then one of A2 to A4 Is CX and the rest of each is CH; or A1 is CX and A4 is N, then A2, A3 and A5 are independently selected from CX and CH; wherein X is independently of each other halogen, C1-C4-alkyl or C1- C4-haloalkyl.

In another preferred group of compounds of formula (I), R1 to R4 are each hydrogen; R5 is substituted or unsubstituted phenyl; R6 is hydrogen or C1-C4-alkyl; R7 Is hydrogen, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl; A1 is in addition to C-halogen, A2 is N and A3, A4 and A5 are independently selected from CX and CH; wherein X is independent of each other The ground is halogen, C1-C4-alkyl or C1-C4-haloalkyl, along with acceptable salts, enantiomers, diastereomers, tautomers and N-oxides thereof. Preferably, in this group of such compounds, A1 is C-C1-C4-haloalkyl, A2 is N, and A3, A4 and A5 are independently selected from CX and CH; wherein X is independently of each other Halogen, C1-C4-alkyl or C1-C4-haloalkyl; preferably, A1 is C-CF3, A2 is N and A3, A4 and A5 are each CH.

In an embodiment, independently of the other embodiments, X is independently of one another halogen or C1-C4-haloalkyl, preferably selected from the group consisting of bromine, chlorine, fluorine, trifluoromethyl and difluoromethyl; It is selected from the group consisting of chlorine, fluorine and trifluoromethyl.

In another preferred group of compounds of formula (I), each of R1 to R4 is hydrogen; R5 is selected From a cyano substituted phenyl group (which may be optionally further substituted by halogen or trifluoromethyl), 2-fluoro-4-trifluoromethylphenyl, 2,6-difluoro-4-chloro -phenyl, 2,4-difluorophenyl, 2,4,6-trifluorophenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-4-bromophenyl, 2-chloro-4- Fluorophenyl, 2-chloro-4-trifluoromethylphenyl, 3,4,5-trifluorophenyl, 2,4-dichloro-6-fluorophenyl, and 2,4-dibromophenyl R6 is hydrogen or C1-C4-alkyl; R7 is hydrogen, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl; and A1 is CX, and A2 to A5 are each CH; or A1 and A5 is each CX, and A2 to A4 are each CH; or A1 is CX, A2 and A5 are each N, and A3 and A4 are each CH; or A1 is CX, A2 is N, and A3 to A5 Each line CH, wherein X is independently selected from halo, C-C4-alkyl or C1-C4-haloalkyl, together with acceptable salts, enantiomers, diastereomers, tautomers thereof Structure and N-oxide.

In another preferred group of compounds of formula (I), R1 to R4 are each hydrogen; R5 is 2,4-chlorophenyl; R6 is hydrogen or C1-C4-alkyl; R7 is hydrogen, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl; and A1 is C-C1, and A2 to A5 are each CH; or A1 is CF, A2 and A5 are each N, and A3 and A4 Each line CH; or A1 and A5 each is C-C1 or C-CF3 and A2 to A4 are each CH; or A1 is CF or C-CF3, A2 is N, and A3 to A5 are each CH; Or A1 & A5 are each N, then A2 to A4 are independently selected from CH, CX and N; or A2 is CX, then A1, A3 to A5 are independently selected from CH, N or CX; or A1 is CX and A5 Line N, then A2 to A4 are independently selected from CX and CH; or A1 is CX and A5 is CH, then one of A2 to A4 is CX and the rest of each is CH; or A1 is CX and A4 is N And then A2, A3 and A5 are independently selected from CX and CH; wherein X is independently of each other halogen, C1-C4-alkyl or C1-C4-halalkyl, together with acceptable salts, enantiomers thereof , diastereomers, Tautomers and N-oxides.

In an embodiment, independent of other embodiments, R5 is substituted phenyl having independently selected from the group consisting of halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkane. a substituent of an oxy group, a C1-C4-haloalkoxy group, or a C3-C6-cycloalkyl group, which is unsubstituted or substituted with one or more substituents Rx, wherein Rx is independently of each other It is selected from the group consisting of halogen, C1-C4-alkyl, and C1-C4-haloalkyl. Preferably, the substituent on the phenyl group at R5 is independently selected from the group consisting of halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4 a haloalkoxy group, and a C3-C6-cycloalkyl group.

In an embodiment, independently of the other embodiments, R5 is a substituted phenyl group having from one to three substituents, preferably two or three substituents, more preferably two substituents.

In embodiments, the phenyl group at R5 is substituted with an optionally substituted phenyl group or an optionally substituted pyrazole, independently of other embodiments. Preferably, the substituents are independently selected from the group consisting of chloro, methyl, fluoro, trifluoromethyl, cyclopropyl and cyano.

In an embodiment, independent of other embodiments, R6 is hydrogen or C1-C2-alkyl, preferably hydrogen.

In an embodiment, independent of other embodiments, R7 is hydrogen.

In an embodiment, independent of the other embodiments, wherein A1 is N or CX, and the groups A2, A3, A4, and A5 are selected from (I) A2, A3, and A4, each CH, and A5 is N; II) A2 is CX, and A3, A4, and A5 are each CH; (III) A3 is CX, and A2, A4, and A5 are each CH; and (IV) A4 is CX, and A2, A3, and A5 are each Family CH.

In an embodiment, independent of other embodiments, wherein A1 & A5 are each N, then A2 to A4 are independently selected from CH, CX, and N.

In an embodiment, independent of other embodiments, wherein A2 is CX, then A1, A3 to A5 are independently selected from CH, N or CX.

In an embodiment, independent of other embodiments, wherein A1 is CX and A5 is N, then A2 to A4 are independently selected from CX and CH.

In an embodiment, independent of other embodiments, A1 is N or C-X, and A2, A3, and A4 are C-H, and A5 is N.

Preferably, in this embodiment, A1 is CX, A2, A3 and A4 are C-H, and A5 is N.

In this embodiment, it is also preferred that A1 is N, A2, A3 and A4 are C-H, and A5 is N.

In an embodiment, independent of other embodiments, A1 is N or C-X, A2 is C-X, and A3, A4, and A5 are each C-H.

In an embodiment, independent of other embodiments, A1 is N or C-X, A3 is C-X, and A2, A4, and A5 are C-H; In an embodiment, independent of other embodiments, A1 is N or C-X, A4 is C-X, and A2, A3, and A5 are each C-H.

In an embodiment, independently of the other embodiments, A1 and A5 are N; and the remainder are independently selected from C-H and C-X.

In an embodiment, independent of other embodiments, A1 is CX, A2, A3, and A5 are each CH, and A4 is CX.

In an embodiment, independent of other embodiments, A1 is CX, A2, A4, and A5 are each CH, and A3 is CX.

In an embodiment, independent of the other embodiments, A1 is CX, A2 and A3 are each CH, A4 is N and A5 is CX.

In an embodiment, independent of other embodiments, in the case where any of A1 to A5 is CX, X in CX is independently selected from the group consisting of halogen, C1-C4-alkyl, and C1-C4-halane. base. Preferred are X-based halogen, OH, C1-C2-alkyl and C1-C2-haloalkyl, especially halogen, methyl and halomethyl, such as trifluoromethyl.

In an embodiment, independently of the other embodiments, A1 is C-C1-C4-haloalkyl, A2 is N, and each of A3, A4, and A5 is C-H.

In an embodiment, independent of other embodiments, A1 is C-X, A2, A3, and A4 are C-H, and A5 is N.

In an embodiment, independent of other embodiments, R6 is hydrogen or C1-C2 alkyl, preferably hydrogen.

In an embodiment, independent of other embodiments, R7 is hydrogen.

In an embodiment, independently of the other embodiments, X in CX of A1 to A5 is independently selected from halogen, C1-C2-alkyl, and C1-C2-haloalkyl; preferably, independently selected From chlorine, fluorine, methyl and trifluoromethyl.

In one aspect, the compound of formula (I) is wherein R1 to R4 are each hydrogen; R5 is substituted or unsubstituted phenyl; R6 is hydrogen or C1-C4-alkyl; R7 is hydrogen, C1- C4-alkylcarbonyl or C1-C4-alkoxycarbonyl; and A1 is CX, A2 and A4 are each N, and A3 & A5 are each CH or A1 is CX, A3 and A5 are each N, and A2 & A4 are each CH; wherein X is independently of each other halogen, C1-C4-alkyl or C1-C4-haloalkyl.

In a preferred embodiment of each of the embodiments described herein, the R5 is from 2 to 3 a substituent-substituted phenyl group, which is independently selected from the group consisting of halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy The group and the C3-C6-cycloalkyl group are preferably chlorine, methyl, fluorine, trifluoromethyl, cyclopropyl and cyano.

In a preferred embodiment of each of the embodiments described herein, the A1 systems CX, A2 and A5 are independently selected from N and CH, and each of A3 & A4 is CH, wherein X is Cl, F or CF3. Preferably, CF3, Cl, and more preferably CF3.

In a particularly preferred embodiment, independently of each embodiment, A1 is CX, A2 is N and A3 to A5 are each CH, wherein X is Cl or CF3, preferably CF3, Cl, more preferably CF3; or A1 is CX, A5 is N and each of A2 to A4 is CH, wherein X is Cl, F or CF3, preferably CF3, Cl, more preferably CF3; or A1 is CX, A2 & A5 Each of the lines N and A3 and A4 is each CH, wherein X is Cl, F or CF3, preferably CF3, Cl, more preferably CF3.

Independent of each embodiment, the preferred ring system of A1 to A5, A1 is C-CF3, and A2 to A5 are each CH; or A1 is C-CF3, A2 and A5 are each N, and A3 and A4 is each CH; or A1 is C-chlorine, A2 and A5 are each N, and A3 and A4 are each CH; or A1 and A5 are each C-fluorine and A2 to A4 are each CH.

Compounds of formula (I) can be prepared from amines of formula (II) and deuteration agents of formula (VII) wherein R1, R2, R3, R4, R5, R6, R7, A1, A2, A3, A4, and A5 are as defined herein and are Xb leaving groups. Typical leaving group is a halide, Preferred are chlorides and hydroxyl groups. When Xb is a hydroxyl group, (VII) is a carboxylic acid, and the reaction is preferably promoted by an activator. Typical activators are, for example, in LaPaquette, Encyclopedia of Reagents for Organic Synthesis, Vol. 3, UK, Willie Press, 1995, pages 1751-1754 (Vol 3 DCC, EDCI, BOP, HBTU, BOP-Cl, PyBOP as described in .Wiley, England, 1995 pp 1751-1754). Deuteration agents of formula (VII) are known or readily prepared by those skilled in the art.

An amine having the formula (IIa) wherein R6 and R7 are H, and R1, R2, R3, R4 and R5 are as defined herein, and the nitrile having formula (III) can be treated by a reducing agent. preparation. A typical reducing agent is hydrogen. Typically, such hydrogenation can be promoted with a catalyst. Typical catalysts are metals, metal salts or metal complexes. Other typical reducing agents are hydrides. Typical hydride borohydrides or aluminum hydrides, examples of which are sodium borohydride, diisobutylaluminum hydride or lithium aluminum hydride. Such hydride reduction can be facilitated by the use of other components such as metal salts.

A compound of formula (IIb) wherein R7 is H, and R1, R2, R3, R4, R5 and R6 are as defined herein, by using an organometallic reagent having the formula R6-Xc The imine of formula (IV) is treated followed by hydrolysis (for example, with an acid such as hydrochloric acid). Xd is an activating group, typically a sulfhydryl, sulfinyl or sulfonyl group. Xc is a metal ion which may be coordinated or uncoordinated with another anion or ligand. A typical R6Xc reagent is a Grignard or organolithium reagent.

Compound (IVa) can be prepared from aldehyde (VI) and sulfinamide of formula (IX) wherein Xf is an alkyl or aryl group, wherein Xd is S(=O)Xf and R1, R2, R3, R4 and R5 are as defined herein. This condensation can be conveniently accomplished in the presence of a dehydrating agent. Typical dehydrating agents are titanium chloride, titanium alkoxide, magnesium sulfate or calcium chloride. The aldehyde having the formula (VI) can be prepared by reduction of the corresponding nitrile (III) or ester, or by oxidation of the corresponding alcohol (for example, SWERN oxidation). One of the reducing agents which can be used to reduce the nitrile or ester to an aldehyde is diisobutylaluminum hydride (DIBAL).

In the presence of a base, there may be a nitrile having the formula (XI) wherein R5 is as defined herein and an alkylating agent having the formula (X) wherein R1, R2, R3 and R4 are as herein A nitrile of formula (III) wherein R1, R2, R3, R4 and R5 are as defined herein, are defined and Xg is a leaving group. Typical leaving groups are halides and sulfonates.

Obviously, the compound of formula (I) can be converted to other formula (I) by the synthetic modification of the groups R1, R2, R3, R4, R5, R6, R7, A1, A2, A3, A4 and A5. Compound. Similarly, such conversion can be carried out on intermediates (II) to (XI).

These reactions can be conveniently carried out in a solvent.

These reactions can be conveniently carried out at different temperatures.

These reactions can be conveniently carried out in an inert atmosphere.

The alkylation of the amines used to derive the compounds of formula (II) is known.

These reactants can be reacted in the presence of a base. Examples of suitable bases are alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal hydrides, alkali metal or alkaline earth metal alkides, alkali metal or alkaline earth metal alkoxides, alkali metal or alkaline earth metal acetates, alkali metals or Alkaline earth metal carbonate, alkali metal or alkaline earth metal dialkyl decylamine or alkali metal or alkaline earth metal alkyl decyl decylamine, alkylamine, alkylenediamine, free or N-alkylated, saturated or Unsaturated cycloalkylamines, basic heterocyclics, ammonium hydroxides, and carbocyclic amines. Examples which may be mentioned are sodium hydroxide, sodium hydride, sodium amide, sodium methoxide, sodium acetate, sodium carbonate, potassium butoxide, potassium hydroxide, potassium carbonate, potassium hydride, lithium diisopropylamide, bis ( Trimethyl indenyl) potassium decylamine, calcium hydride, triethylamine, diisopropylethylamine, triethylamine, cyclohexylamine, N-cyclohexyl-N,N-dimethylamine, N, N-diethylaniline, pyridine, 4-(N,N-dimethylamino)pyridine, Pyridine, N-methyl Porphyrin, benzyltrimethylammonium hydroxide and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

The reactants can be reacted with each other as they are, i.e., without the addition of a solvent or diluent. However, in most cases, it is advantageous to add an inert solvent or diluent or a mixture thereof. If the reaction is carried out in the presence of a base, the bases used in excess (such as triethylamine, pyridine, N-methyl) Or N,N-diethylaniline can also be used as a solvent or diluent.

The reaction is advantageously carried out at a temperature of from about -80 ° C to about +140 ° C, preferably from about -30 ° C to about +100 ° C, in many cases at ambient temperature and about +80 ° C. between.

A compound of formula (I) can be converted into another compound of formula (I) by a method known per se by one or more of the compounds of formula (I) which are initiated in a conventional manner Substituents are achieved by substitution with another substituent or substituents according to the invention.

Depending on the reaction conditions selected as appropriate and the starting materials, it is possible, for example, to replace only one substituent with another substituent according to the invention in one reaction step, or in the same reaction step The substituents are replaced by a plurality of other substituents according to the invention.

Salts of the compounds of the formula (I) can be prepared in a manner known per se. Thus, for example, an acid addition salt of a compound of formula (I) is obtained by treatment with a suitable acid or a suitable ion exchange reagent, and the salt with a base is used by using a suitable base or A suitable ion exchange reagent is obtained by treatment. The salt is selected depending on the admissibility of the salt for the use of the compound, such as agricultural or physiological tolerance.

Salts of the compounds of formula (I) can be converted in the conventional manner to the free compound I, the acid addition salt (for example by treatment with a suitable basic compound or with a suitable ion exchange reagent) and a salt with a base (for example by treatment with a suitable acid or with a suitable ion exchange reagent).

The salts of the compounds of the formula (I) can be converted into other salts of the compounds of the formula (I) in a manner known per se, for example by converting the acid addition salts into further acid addition salts, for example in a suitable solvent The treatment of a salt of a mineral acid (such as a hydrochloride salt) with a suitable metal salt of an acid (such as sodium, cesium or a silver salt), for example, by treating silver acetate with an acid, the inorganic salt formed in the solvent (for example silver chloride) is insoluble and thus precipitates out of the reaction mixture.

Depending on the procedure or reaction conditions, the compounds of formula (I) having salt forming properties can be obtained in free form or in the form of a salt.

The mixture of diastereomers or racemates of the compound of formula (I) in free form or in salt form, which may be obtained depending on the starting materials and procedures selected, are capable of such components The physicochemical differences are separated into pure diastereomers or racemates in a known manner, for example by fractional crystallization, distillation and/or chromatography.

Enantiomeric mixtures (such as racemates) can be obtained by analogous methods which can be resolved into optical antipodes by known methods, for example, by recrystallization using an optically active solvent; By using chiral adsorbent chromatography, such as acetonitrile cellulose high performance liquid chromatography (HPLC); with the aid of suitable microorganisms, by using specific immobilized enzymes; only one type of mapping In the case where the isomer is complexed, via formation of the inclusion compound, for example using a chiral crown ether; or by conversion to a salt of the diastereomer, for example by the racemic body of the basic terminal product An optically active acid such as a carboxylic acid such as camphoric acid, tartaric acid or malic acid, or a sulfonic acid such as camphorsulfonic acid is reacted and the mixture of diastereomers obtainable by this method is separated (for example) The diastereomers are given by fractional crystallization according to their different solubility, and the desired diastereomers can be released from the desired diastereomers by the action of a suitable reagent such as an alkaline reagent. Enantiomer

Pure diastereomers or enantiomers can be obtained according to the invention, not only by separation of suitable isomer mixtures, but also by generally known diastereoselective or enantiomeric A method of selective synthesis, for example by carrying out the process according to the invention using suitable stereochemical starting materials according to the invention.

The N-oxide can be prepared by reacting a compound of formula (I) with a suitable oxidizing agent (e.g., H ₂ O ₂ / urea adduct) in the presence of an acid anhydride (e.g., trifluoroacetic anhydride). . Such oxidation can be found in the literature, for example from J. Med. Chem., 32 (12), 2561-73, 1989 or WO 00/15615 or C. White, Science ( Science, Vol. 318, page 783, 2007 (vol 318, p. 783, 2007) is known.

If the individual components have different biological activities, it is advantageous to isolate or synthesize biologically more efficient isomers, such as enantiomers or diastereomers, or A mixture of constructs, such as an enantiomeric mixture or a mixture of diastereomers.

If appropriate, the compounds of the formula (I) in each case in free form or in the form of a salt and, where appropriate, their tautomers can also be obtained in the form of hydrates and/or include other solvents, for example Those which can be used for the crystallization of compounds which exist in solid form.

Specific examples of compounds having formula (I) are shown in Table P below: among them

Compounds of formula (I) have been found to control damage caused by pests and/or fungi.

In an embodiment, a compound of formula (I) can be used in agriculture.

Accordingly, the invention further provides a method of controlling damage and/or yield loss caused by pests and/or fungi, the method comprising applying an effective amount of a compound of formula (I) to a pest, pest site, or On plants, or plant propagation materials that are attacked by pests and/or fungi.

The compounds according to the invention can be used for control, ie limitation or destruction, on plants, especially on plants, especially in useful plants and ornamental plants in agriculture, horticulture and forests, or Pests and/or fungi on flowers, leaves, stems, roots, seeds or roots, and in some cases, even on plant organs formed at later time points, remain protected from such pests.

The compounds of formula (I) according to the invention are pre-determined in the field of pest control Anti- and/or therapeutically valuable active ingredients, even if applied at low application rates, can be used against pesticidal pests and fungi, such compounds having formula (I) being highly advantageous The biocidal range is well tolerated by warm-blooded species, fish and plants.

The compounds according to the invention act on all or individual developmental stages of normally sensitive and also drug-resistant animal pests such as insects or eye-catching representatives. The insecticidal or acaricidal activity of the compounds according to the invention may manifest themselves directly, ie for example the destruction of the pest during molting, which occurs immediately or only after a certain period of time; or indirectly manifests itself, for example Reduced spawning and/or hatching rates, good activity corresponds to a destruction rate (mortality) of at least 50% to 60%.

Examples of the above-mentioned animal pests are: from the order of the order, for example, Acalitus spp., Aculus spp., Acaricalus spp., genus, thick feet Whitefly, blunt-eye genus, genus Quercus, burdock , genus, genus, genus, genus Calipitrimerus spp., genus, pheasant, echinoderma , epidermis Eriophyes spp., E. striata , genus, genus, genus Olygonychus spp., blunt genus, polyphagia, Phyllostachys pubescens, Phytonmus spp., Polyphagotarsonemus spp., genus genus, genus, genus, genus, genus A genus of the genus Aphididae, Aphis genus, and Aphis genus; from the order of the genus Aphis, for example, the genus Helicover, the genus, the genus, the genus Pestle, and the hibiscus; from the coleoptera, for example, the scorpion Genus, European horned tortoise ( Amphimallon majale ), Oriental genus, genus, genus, Astylus atromaculatus , Ataenius spp., Atomaria linearis , Chaetocnema tibialis, Cerotoma spp. Chest beetle genus Elephas crown, Cotinis nitida, like genus, Cyclocephala spp., is a beetle, Diabrotica spp., Argentina pocket insects, ladybugs eat plant genus, Eremnus spp. , Black-clawed cane tortoise, coffee fruit scorpion , Lagria vilosa , potato leaf genus, rice water genus, Liogenys spp., Maecolaspis spp., gilt tortoise, Megascelis spp., rape flower tail, golden turtle, Myochrous armatus , Sawgrass , Deafness , genus, genus Phlyctinus spp., genus, genus, Rhyssomatus aubtilis , genus, chafer, genus, genus Somaticus spp., genus, genus, genus, genus, genus, and genus; from the order Diptera, for example, Aedes, Anopheles, Antherigona soccata , Bactrocea oleae , Garden Mosquito, Sharp-eyed Mosquito, Red-headed Fly, Lepidoptera, Drosophila, Culex, Yellow Fly, Fruit Fly, Delia spp., Drosophila melanogaster, Genus, genus, Geomyza tripunctata , tsetse fly Genus, genus, genus, genus, genus, genus, genus, genus, genus, genus, genus, genus, genus, genus, genus, genus, genus Fruit fly, Rivelia quadrifasciata , Scatella spp., Aphis , genus, genus, genus, and genus; from Hemiptera, for example, Acanthocoris scabrator , Eucalyptus, 苜蓿 , Amblypelta nitida , Bathycoelia thalassina , genus genus, bedbug, Clavigralla tomentosicollis , Creontiades spp., cocoa scorpion , Dichelops furcatus , cotton red genus, Edessa spp., Euchistus spp., scutellaria , scutellaria , tea Winged owl , Horcias nobilellus , Lycium genus, Lycium genus, Lycium genus, Murgantia histrionic , Neomegalotomus spp., Sphagnum , Green genus, Nysius simulans , Oebalus insularis , Piesma spp., genus, red Aphis , Cocoa, Scaptocoris castanea , Aphis , Thyanta spp., Cone, Vatiga illudens ; from Homoptera, for example, Acyrthosium pisum , Adalges spp., A Galliana ensigera , Agonoscena targionii , Amaranthus , Aquilaria , Aleurolobus barodensis , Amaranthus , Aleyrodes brassicae , Amarasca biguttula , Amritodus atkinsoni , Astragalus genus, Aphididae, Aphis, Astragalus , Aster Netless , Bactericera cockerelli , Brassica, Brachycaudus spp., Brassica, Kasuga , Cavariella aegopodii Scop , Ceroplaster spp., Chrysomphalus aonidium , Chrysomphalus dictyospermi , Amaranthus , Great White Leaf , Cryptomyzus spp., Cicadulina Spp., brown soft glutinous rice, corn yellow leafhopper, naked genus, citrus hibiscus, wheat double-tailed pheasant , western genus, genus, genus Eriosoma larigerum , genus genus, genus , Red hibiscus , Hyadaphis pseudobrassicae , Hyalopterus spp., Hyperomyzus pallidus , Mango green leaf Jacob , Jacobiasca lybica , Laodelphis, Ball 蚧 , 蛎 蚧 , Lopaphis erysimi , Lyogenys maidis , Aphis genus, Moss Genus, Metcalfa pruinosa , Mai no net long tube, Myndus crudus , genus Neotoxoptera spp., Black-tailed genus, BPH, Nippolachnus piri Mats , Odonaspis ruthae , Oregma lanigera Zehnter , Parabemisia myricae , Paratrioza cockerelli , Shield genus, Aphis genus, Corn wax mites , Perkinsiella spp. Suspension , genus, genus, genus, genus, genus, genus, genus, genus Pulvinaria aethiopica , genus genus, Quesada gigas , electro-optic leaf scorpion Genus, genus, genus, genus, genus, genus, genus, white-backed locust , Spissistilus festinus , Tarophagus Proserpina , scorpion , white genus, Tridiscus sporoboli , genus African hibiscus , scorpion scorpion , Zygina flammigera , Zyginidia scutellaris ; from Hymenoptera, for example, argyi genus, Arge spp., Atta spp., genus, genus , saw angle Tenthredinidae, pine sawfly (Gilpinia polytoma), real sawfly species, genera Lasius, small yellow house ants, pine sawfly is a new, harvester ant genera, Slenopsis invicta, water ants and wasps belong to the genus; Since the Isoptera, for example, is a termite, Corniternes cumulans, Ying belongs to termites, termites belong, Australia termites is a small genus of termites, termite genera; tropical fire ants from the Lepidoptera, for example, long-winged moth genus, brown with genus pomonella, tabaniformis, genus Helicoverpa, cotton leaf worm, Amylois spp., Anticarsia gemmatalis, yellow moth genus, Argyresthia spp., with moth genus, genus Ah looper, cotton latent Moth, corn worm, corn moth, peach worm, grass genus, leaf genus, Chrysoteuchia topiaria , grape fruit moth, leaf genus, genus, genus, stalk Moth, Fructus fragrans , Cosmophila flava , Crambus spp., Brassica oleracea L. , Apple genus Moth, Cydalima perspectalis , Cyprinus genus, Populus euphratica, Syzygium , Sudan bollworm, Diamond genus, African stalk, white genus, genus, genus, Etiella zinckinella , genus, genus, genus, genus, genus Feltia jaculiferia , genus Grapholita spp), green budworm moth, heliothis spp., cabbage , Herpetogramma spp., Fall webworm, tomato moth, Lasmopalpus lignosellus, rotation pattern leafminer, leaf miner species, Putaohua wing pomonella, Loxostege bifidalis, is a moth, leafminer spp., Curtain leaves moth genus, Spodoptera frugiperda, Tobacco hawkmoth, Mythimna spp., Noctuidae, A. genus, Orniodes indica , European corn borer, Ultramania, Alternaria , Spodoptera frugiperda, Spodoptera litura, Pectinophora Gossypiela , coffee leaf miner , one-star armyworm, potato tuber moth, cabbage butterfly, Pieridae, Plutella xylostella , Spodoptera, Spodoptera, Rachiplusia nu , Richia albicosta , White genus, Spodoptera litura Genus, genus, genus, genus, genus, genus, genus, genus, genus, genus, genus, genus, and genus From the order of the genus, such as the genus Damalina spp. and the genus Lepidoptera; from the order of the Orthoptera, for example, genus, genus, genus, genus, genus, genus, northern genus, Euphorbia, genus, and desert genus; from the genus, for example , from the order of the genus, from the order of the genus, for example, the genus Acanthus , the genus genus and the genus of the genus; from the order of the pteridophyte , for example, Calliothrips phaseoli , the flower genus, the genus Yangshuo , the brown belt hummer Genus, Parthenothrips spp., South African citrus thrips, soybean thrips, genus Thrips and genus Thrips; from the appendix, for example, squid.

In a further aspect, the invention may also be directed to a method for controlling or preventing the infestation of a useful plant by a phytopathogenic microorganism, wherein a compound of formula (I) is administered 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 activity, good plant tolerance and are environmentally safe. They have very useful therapeutic, prophylactic and systemic properties and are used to protect a wide variety of useful plants. a compound of formula (I) It can be used to inhibit or destroy diseases occurring on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of different useful plants, while also protecting those plant parts that grow later, for example, to avoid phytopathogenic microorganisms. Infringement. It is also possible to use a compound of the formula (I) as a seed dressing for the treatment of plant propagation material, in particular seeds (fruits, tubers, grains) and plant cuttings (for example rice) for protection against fungal invasion. Dyeing together with phytopathogenic fungi that are present in the soil.

Examples of fungi include: deuteromycetes (for example, Botrytis, Trichosporon, Helminthosporium, Fusarium, Neurospora, Cercospora, and Alternaria); Basidiomycetes (for example, Rhizoctonia, Phytophthora genus, genus Puccinia; Ascomycetes (for example, genus of the genus Staphylococcus and powdery mildew, genus Fork, genus Candida, genus H.); Oomycetes (eg, Phytophthora, Pythium, Monotrichum ); Zygomycetes (eg, Rhizopus); Phakopsoraceae , especially those of the genus Puccinia, eg Pleurotus ostreatus, also known as Asian soybean rust, and those of the genus Puccinia, especially those of the genus Puccinia, such as Pleurotus ostreatus, also known as stem rust or black rust, The problematic disease in cereal plants, as well as the rust fungus, also known as brown rust.

Among the plants protected by the method according to the invention and possible diseases of such plants, mention may be made of: wheat, for controlling the following seed diseases: Fusarium (Microdochium) Nivale) and Fusarium oxysporum), sorghum smut (S. sphaeroides, smut of wheat dwarf smut or smut of wheat smut), sclerotium disease (spotted sphaeroides) and black Powder disease; wheat, the following diseases that control the aerial parts of plants: cereal eyespot (Tapesia yallundae, Tapesia acuiformis), total eclipse (odly omega), base blight (foot blight) ( Fusarium oxysporum, Fusarium graminearum), black speck (Rh. rhizogenes), powdery mildew (Erysiphe graminis forma specie tritici), rust (rod rust and stem stalk) Rust fungus and Phytophthora disease (Saccharomyces cerevisiae and A. oxysporum); Wheat and barley, for controlling bacterial and viral diseases such as barley yellow mosaic disease; Barley, for controlling the following seed diseases : net blotch (marine nucleus, nucleus and Helminthosporium), black powder fungus (naked black powder fungus) and Fusarium (grass pink snow mold) Microdochium nivale) and Fusarium oxysporum; barley, about the following diseases controlling the aerial parts of plants: Tapesia yallundae, net blotch (Centidae and Helminthosporium) , Erysiphe graminis forma specie hordei, dwarf leaf rust (barley rust) and leaf blotch (barley mutans); potato, about controlling tuber disease (especially potatoes) Psoriasis, Phoma tuberosa, eggplant Nuclear bacteria, Fusarium solani), mildew (Plrytopthora infestans) and certain viruses (virus Y); potato, for controlling the following leaf diseases: early blight (Alternaria solani), mildew (Plrytopthora infestans); cotton , for controlling the following diseases of young plants grown from seeds: squatting disease and collar rot (String rot fungi, Fusarium oxysporum) and root black rot (C. fulvum); protein-producing plants For example, peas, for controlling the following seed diseases: anthracnose (P. pea, pea brown), Fusarium (Fusarium oxysporum), Botrytis (Botrytis cinerea) and mold (Pythium pea) Oily plants, such as canola, about controlling the following seed diseases: cabbage black stem disease, cabbage black Spot disease and rapeseed sclerotinia; corn, for controlling seed diseases: (Rhizophyta, Penicillium, [0104] Trichoderma, Aspergillus, and Gibberella); Flax, about controlling seed diseases: Alternaria linicola; forest trees , for controlling sputum disease (Fusarium oxysporum, Rhizoctonia solani); rice, for controlling the above-mentioned diseases of the aboveground part: rice blast (rice blast fungus), bordered sheath spot (Spirulina solani) Legumes, diseases that control the following seed diseases or young plants grown from seeds: rickets and collar rot (Fusarium oxysporum, Fusarium oxysporum, Rhizoctonia solani, Pythium Genus), a leguminous plant, for controlling the above-mentioned diseases of the aerial part: Botrytis cinerea (Botrytis), powdery mildew (especially Erysiphe cichoracearum, Sphaerotheca fuliginea, and Leveillula taurica) ), Fusarium (Fusarium oxysporum, Fusarium oxysporum), leaf spot (sporocystis), Alternaria leaf spot (Alternaria), anthracnose (Anthracnose) ), Capreolus leaf spot (shell needle) Genus), black speck (myenus), mildew (eg, downy mildew, downy mildew, pseudomonas, Phytophthora); fruit trees, diseases on the ground: Candida Is a disease (Monilia fructigenae, Phytophthora), spot disease (Apple black spot), powdery mildew (apple powdery mildew); - vine, about leaf disease: especially gray mold (Botrytis cinerea), powdery mildew (grape crochet), black rot (Guignardia biwelli) and mildew (grape downy mildew); beetroot, the following diseases on the aerial part: cercospora blight (Cercospora beticola) ), powdery mildew (Erysiphe beticola), leaf spot (beet) Leaf spot pathogen).

The fungicide composition according to the invention can also be used against fungal diseases which are easy to grow on wood or inside the wood. The term "wood" means all types of wood species and all types of wood that are expected to be used in construction, such as solid wood, high density wood, laminates, and plywood. The method of treating wood according to the invention consists essentially of: contacting one or more compounds of the invention, or a composition according to the invention; this includes, for example, direct application, spraying, dipping, injecting or any other suitable method. .

In a further aspect, the invention also relates to a method of controlling damage to plants or parts thereof by plant parasitic nematodes (endoparasites, semi-endoparasites, and ectoparasites), in particular the following plant-parasitic nematodes, such as root-knot nematodes, Northern root-knot nematode, southern root-knot nematode, Javanese root-knot nematode, peanut root-knot nematode and other root-knot nematode species; cyst-forming nematodes, potato golden nematodes and other cyst nematode species; cyst nematode, Soybean cyst nematode, sugar beet cyst nematode, Heterodera trifolii , and other heterologous nematodes; seed nematodes, elegans; stems and leaf nematodes, Nematodes; Sting nematodes, Eelonolaimus longicaudatus and other species of the genus Thornworm ; Pine nematodes, Bursaphelenchus xylophilus and other species of the genus Umbrella; Ring nematodes ring species, small ring insect species, to be insect species ring, Mesocriconema species; stem and bulb nematodes, rot Nematodes, Dipsacus bis Tylenchida nematode and other bis Tylenchida species; cone nematodes (Awl nematodes), cone Strongyloides (Dolichodorus) species; Spiral nematodes (Spiral nematodes), long spiral nematode (Heliocotylenchus multicinctus) and other spiral Nematode species; sheath nematode and close nematodes, Hemicycliophora species and Hemicriconemoides species; Latent nematode species; Lance nematodes, Hoploaimus species; Pseudo-root nematodes, Pearl nematode species; needle nematodes, long needle nematodes and other species of the long-necked nematode; needle-shaped nematodes, short- living nematode species; rot nematodes, off-species nematodes ( pratylenchus neglectus ), short- stem nematodes, curved short- stem nematodes (Pratylenchus curvitatus), Pratylenchus goodeyi and other short- stem nematode species; Burrowing nematodes, banana perforating nematodes and other perforated nematode species; kidney-shaped nematodes, Roche's hovering nematode ( Rotylenchus robustus), banana nematodes and other kidney-shaped disk Nematode species; shield-like nematode genera (Scutellonema) species; stubby root nematodes, Trichodorus original and other Trichodorus species, Paratrichodorus nematode species; Tylenchorhynchus (Stunt nematodes), Clayton Tylenchorhunchus , undecided nematode ( Tylenchorhynchus dubius ) and other dwarf nematode species; citrus nematodes, C. elegans; Dagger nematodes, S. genus species; and other plant-parasitic nematode species, such as Subanguina spp. , Hypsoperine spp., Macroposthonia spp., Melinius spp., Cysts , and Quinisulcius spp.

The compounds of the invention may also have activity against molluscs. Examples of mollusks include, for example, apple snail; Arion (black scorpion, A. circumscriptus, A. hortensis, A. rufus); snail family (Bradybaena fruticum); snail genus (garden onion snail, land snail); ochlodina ; wild genus (D.agrestis, D.empiricorum, wild pheasant, reticulata); Discus (D.rotundatus); Euomphalia; G. trunculata; large snail (Italian Large snail (H.itala), H.obvia); Large snail family (Helicigona arbustorum); Helicicoscus; Helix (H. apeita); genus (Limacos 蛞蝓, Astragalus, L. marginatus, large蛞蝓, 蛞蝓 蛞蝓 (L.tenellus); vertebrate; Milax (M. Gagates, M. marginatus, M.sowerbyi); genus Drosophila; P. canaticulata; snail snail and Zanitoides. The combination according to the invention is particularly effective against wild genus, such as reticulated mites.

In an embodiment, the compound of formula (I) is especially useful for controlling nematodes, independent of other embodiments. In particular, the compounds of the invention can be used to control nematode species of the genus K. elegans, the genus Heterodera, the genus Trichoderma, and the genus Short worm.

When used alone, the compounds of the invention are effective in controlling nematodes, insects, aphid pests and/or fungal pathogens in growing or already harvested agronomic plants, and they may also be used in other agricultural uses. The active agents are used in combination, such as one or more nematicides, insecticides, acaricides, fungicides, bactericides, plant activators, molluscicides, and pheromones (chemical or biological). Mixing a compound of the invention or its combination in the form of a pesticide-killing agent with other pesticides often results in a broader range of pesticidal action. For example, a compound of formula (I) of the present invention can be used effectively in combination or combination with pyrethroids, neonicotinoids, macrolides, diamines, phosphates, amines. Acid esters, cyclodienes, formamidine, phenol tin compounds, chlorinated hydrocarbons, benzhydrylphenyl urea, pyrrole and the like.

By incorporating, for example, one or more insecticidal, acaricidal, nematicidal and/or fungicidal active agents, the activity of the compositions according to the invention can be greatly broadened and suitable for the dominant situation. Combinations of compounds of formula (I) with other insecticidal, acaricidal, nematicidal and/or fungicidal active agents may also have other unexpected advantages which may also be described in a broader sense, such as synergistic activity . For example, better plant tolerance, reduced phytotoxicity, control of pests or fungi at different developmental stages, or during production of such combinations (eg, Better behavior during grinding or mixing), during their storage, or during their use.

The following list of pesticides with which the compounds according to the invention can be used together is intended to demonstrate possible combinations by way of example.

The following combinations of compounds of formula (I) with other active compounds are preferred (abbreviated "TX" means "a compound selected from the formulae P.1 to P as described in Table P of the present invention. Compound of "191": an adjuvant selected from the group consisting of petroleum (alias) (628) + TX, an acaricide selected from the group consisting of: 1,1 - bis(4-chlorophenyl)-2-ethoxyethanol (IUPAC name) (910) + TX, 2,4-dichlorophenyl benzene sulfonate (IUPAC / Chemical Abstracts) (1059) + TX , 2-fluoro-N-methyl-N-1-naphthylacetamide (IUPAC name) (1295) + TX, 4-chlorophenylphenyl hydrazine (IUPAC name) (981) + TX, avermectin (1) +TX, cockroach (3) + TX, acetaminophen [CCN] + TX, flumethrin (9) + TX, aldicarb (16) + TX, annihilation (863 ) +TX, alpha-cypermethrin (202) + TX, thiophene (870) + TX, amidoflumet [CCN] + TX, amidothioate (872) + TX, amine phosphorus (875) + TX, amine phosphatic acid Salt (875) + TX, amitraz (24) + TX, aramite (881) + TX, arsenic trioxide (882) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) +TX, azinphos-ethyl (44 ) +TX, azinphos-methyl (45) + TX, azobenzene (IUPAC name) (888) + TX, azocyclotin (46) + TX, azothoate (azothoate) 889)+TX, benomyl (62)+TX, benoxafos (alias) [CCN]+TX, benzoximate (71)+TX, benzyl benzoate (IUPAC name) [CCN]+TX, biphenyl decyl ester (74) + TX, flumethrin (76) + TX, chlorpyrifos (907) + TX, fenthrin (alias) + TX, bromobenzene (bromocyclene) ) (918) + TX, bromothion (920) + TX, ethyl bromothion (921) + TX, bromopropylate (94) + TX, buprofezin (99) + TX, butanone Wei (103)+TX, butanone oxime (104)+TX, butanone (butylpyridaben) (alias)+TX, calcium polysulfide (IUPAC name) (111)+TX, campheechlor ) (941) + TX, carbanolate (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, carbophil (947) + TX , CGA 50'439 (development code) (125) + TX, chinomethionat (126) + TX, chlorbenside (959) + TX, insecticidal 964 (964) + TX, insecticidal Bismuth hydrochloride (964) + TX, chlorfenapyr (130) + TX, propanil (968) + TX, chlorfenson (970) + T X, chlorfensulphide (971) + TX, chlorpheniramine (131) + TX, ethyl chlorobenzilate (975) + TX, chloromebuform (977) + TX, extinction Chloromethiuron (978)+TX, propylpropyl chloropropylate (983)+TX, chlorpyrifos (145)+TX, methyl chlorpyrifos (146)+TX, chlorthiophos (994) +TX, cinerin I (696) + TX, fenvalerate 11 (696) + TX, cinerins (696) + TX, tetrazine (158) + TX, chlorocyanide Sultanide (alias) [CCN]+TX, Kuma phosphorus (174)+TX, clomiphene (alias) [CCN]+TX, crotoxyphos (1010)+TX, thiazepine (1013) ) +TX, cyanthoate (1020) + TX, butylated fluoro ester (CAS registration number: 400882-07-7) + TX, cyhalothrin (196) + TX, tricyclic tin ( 199)+TX, cypermethrin (201)+TX, DCPM(1032)+TX, DDT(219)+TX, delephion (1037)+TX, Tianle phosphorus-O(1037)+TX, Tian Lephos-S(1037)+TX, demeton (1038)+TX, methyl endophos (224)+TX, inhaled phosphorus-O(1038)+TX, methyl endophos- O(224)+TX, inhaled phosphorus-S(1038)+TX, methyl endophos-S(224)+TX, inhaled phosphorus-S-methylsulfuron (demeton-S- Methylsulphon)(1039)+TX, chlorpyrifos (226)+TX, dialifos (1042)+TX, diazinon (227)+TX, phenylsulfonamide (230)+TX, dichlorvos (236)+TX, dicliphos (alias)+TX, Kailesan (242)+TX, Baizhi phosphorus (243)+TX, ubiquitin (1071)+TX, methotrexate (dimefox) (1081)+TX, dimethoate (262)+TX, dinactin (alias) (653)+TX, decylphenol (1089)+TX, decylphenol (dinex- Diclexine)(1089)+TX, dinobuton (269)+TX, dinocap (270)+TX, enemy -4普-4[CCN]+TX, enemy -6-6[CCN ]+TX, dinitrate (1090)+TX, dinopenton (1092)+TX, dinosulfon (1097)+TX, dinotterbon (1098)+TX, enemies Phosphorus (1102)+TX, diphenylguanidine (IUPAC name) (1103)+TX, disulfiram (alias)[CCN]+TX, bismuth phosphorus (278)+TX, DNOC(282)+TX, benzene Dofenapyn (1113) + TX, doramectin (alias) [CCN] + TX, endosulfan (294) + TX, endothion (1121) + TX, EPN (297) + TX , erinoknine (alias) [CCN]+TX, ethion (309)+TX, ethoate-methyl (1134)+TX, etoxazole (320)+TX, Ethyl pyrimidine Ethion (etrimfos) (1142) + TX, anti-carbazole (fenazaflor) (1147) + TX, quinacridone (328) + TX, phenbutin oxide (330) + TX, fensulfide (fenothiocarb) (337) + TX, fenpropathrin (342) + TX, pyridoxamine (alias) + TX, fenpyroximate (345) + TX, fenson (fenson) (1157) +TX, fentrifanil (1161) + TX, fenvalerate (349) + TX, fipronil (354) + TX, fluacrypyrim (360) + TX, fluzolone (1166) + TX, flubenzimine (1167) + TX, fluoroquinone urea (366) + TX, flucythrinate (367) + TX, fluenetil (1169) +TX, flubendiamide (370) + TX, flumethrin (372) + TX, fluorbenside (1174) + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) + TX, anti-mite (405) + TX, anti-hydrazine hydrochloride (405) + TX, formothion (1192) + TX, amine A. (formparanate) (1193) + TX, γ-HCH (430) + TX, glyodin (1205) + TX, benzyl ester (halfenprox) (424) + TX, heptenophos (432) )+TX, hexadecylcyclopropanecarboxylate (IUPAC/Chemical Abstracts) (1216)+T X, thiazolone (441) + TX, methyl iodide (IUPAC name) (542) + TX, isocarbophos (alias) (473) + TX, isopropyl O -(Methoxyaminothiophosphonyl)salicylate (IUPAC name) (473)+TX, ivermectin (alias) [CCN]+TX, jasmolin I (696) +TX, jasperate II (696) + TX, jodfenphos (1248) + TX, lindane (430) + TX, guanidine urea (490) + TX, malathion (492) + TX , benzylmalononitrile (1254) + TX, mecarbam (502) + TX, methamphetamine (1261) + TX, methylthiophene (alias) [CCN] + TX, Methacrifos (1266) + TX, methamidophos (527) + TX, chlorpyrifos (529) + TX, chlorfenapyr (530) + TX, worms (531) + TX, methyl bromide (537) ) +TX, metolcarb (550) + TX, fast-acting phosphorus (556) + TX, mexacarbate (1290) + TX, milrin (557) + TX, bacteriocin Milbemycin oxime (alias) [CCN]+TX, mipafox (1293)+TX, monocrotophos (561)+TX, morphothion (1300)+TX, moxake D(alias)[CCN]+TX, naled (567)+TX, NC-184 (compound code)+TX, NC-152 (compound code)+TX, nifluridide (1309) ) +TX, nicotimycin (alias) [CCN] + TX, nitrilacarb (1313) + TX, nitrilacarb 1 1 zinc chloride complex (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, omethoate (594) + TX, kill line (602 ) +TX, oxydeprofos (1324) + TX, oxydisulfoton (1325) + TX, pp'-DDT (219) + TX, parathion (615) + TX, chlor chrysanthemum Ester (626) + TX, petroleum (alias) (628) + TX, fenthion (1330) + TX, Daofeng San (631) + TX, phorate (636) + TX, sulforaphane (637 +TX, phosfolan (1338) + TX, imipenem (638) + TX, phosphine (639) + TX, phoxim (642) + TX, methyl pyrimidine (652) +TX, polychloroterpenes (traditional name) (1347) + TX, polynactins (alias) (653) + TX, prochlor (1350) + TX, profenofos (662) +TX, promacyl (1354)+TX, gram (671)+TX, propetamphos (673)+TX, propoxur (678)+TX, prothidathion (1360) + TX, prothoate (1362) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrin (pyrethrins) (696) +TX, 哒螨灵(699)+TX,嗒 Pyridaphenthion (701) + TX, pyrimidin (706) + TX, pyrisulfur (1370) + TX, quinalphos (711) + TX, quintifos (quintiofos) (1381) + TX, R-1492 (development code) (1382) + TX, RA-17 (development code) (1383) + TX, rotenone (722) + TX, octapyl (schradan) (1389) + TX , sulphur phosphorus (sebufos) (alias) + TX, selalectin (alias) [CCN] + TX, SI-0009 (compound code) + TX, sophamide (1402) + TX , keto oxime ester (738) + TX, spironolactone (739) + TX, SSI-121 (development code) (1404) + TX, sufrolon (alias) [CCN] + TX, sulfluramid ( Sulfluramid) (750) + TX, sulfotep (753) + TX, sulfur (754) + TX, SZI-121 (development code) (757) + TX, fluvalinate (398) + TX, pyridoxamine (763) + TX, TEPP (1417) + TX, tertiary tributyl (terbam) (alias) + TX, stilbene (777) + TX, tetradifon (tetradifon) 786) + TX, tetranactin (alias) (653) + TX, tetrasul (1425) + TX, thiafenox (alias) + TX, anti-insect ( Thiocarboxime)(1431)+TX, thiofanox (800)+TX, thiometon (801)+TX, gram Killing (1436) + TX, thuringiensin (alias) [CCN] + TX, triamiphos (1441) + TX, triarathene (1443) + TX, triazole Phosphorus (820)+TX, triazuron (alias)+TX, trichlorfon (824)+TX, trifenofos (1455)+TX, trinactin (alias) (653) + TX, thiophene (847) + TX, vaniliprole [CCN] and YI-5302 (compound code) + TX, algicide, selected from the group consisting of Group consisting of 3-benzo[b]thiophen-2-yl-5,6-dihydro-1,4,2- Thio -4-oxide [CCN]+TX, copper dioctoate (IUPAC name) (170)+TX, copper sulfate (172)+TX, cybutryne[CCN]+TX, dihydronaphthoquinone (dichlone) (1052)+ TX, dichlorophenol (232) + TX, yoghurt (295) + TX, triphenyltin (347) + TX, slaked lime [CCN] + TX, sodium sam (nabam) (566) + TX Quinoclamine (714)+TX, quinonamid (1379)+TX, simazine (730)+TX, triphenyltin acetate (IUPAC name) (347) and hydroxide III Benzoquinone (IUPAC name) (347) + TX, an anthelminating agent selected from the group consisting of avermectin (1) + TX, clanilide (1011) + TX, Doramectin (alias) [CCN]+TX, EMAG (291)+TX, EMAG benzoate (291)+TX, erinoquinine (alias)[CCN]+TX, Ivey Phytocin (alias) [CCN]+TX, milbemycin (alias) [CCN]+TX, moxidectin (alias) [CCN]+TX, piperazine [CCN]+TX, selamectin (alias) [CCN]+TX, spinosyn (737) and thiophanate (1435)+TX, bird killing agent, the birdicide selection Free group consisting of chloralose (127) + TX, endrin (1122) + TX, fenthion (346) + TX, pyridin-4-amine (IUPAC name) (23) and Ning (745) + TX, bactericide, the bactericide is selected from the group consisting of 1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222) + TX, 4- (quin Oxalin-2-ylamino) benzenesulfonamide (IUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctoate (IUPAC name ) (170) + TX, copper hydroxide (IUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophenol (232) + TX, dipyridyl (1105) + TX, dodexin (1112)+TX, fenaminosulf (1144)+TX, formaldehyde (404)+TX, mercury plus fen (alias)[CCN]+TX, chunleimycin (483)+TX, chunremycin hydrochloride Salt hydrate (483) + TX, bis (dimethyl dithiocarbamate) nickel (IUPAC name) (1308) + TX, trichloromethyl pyridine (nitrapyrin) (580) + TX, octothia Ketone (octhilinone) (590) + TX, oxolinic acid (606) + TX, oxytetracycline (611) + TX, hydroxyquinoline potassium sulfate (446) + TX, allylthiazole (probenazole) (658) +TX, streptomycin (744)+TX, streptomycin sesquisulfate (744)+TX, leaf cumin (766)+TX, and thiomersal (alias)[CCN]+TX, biological reagent, the organism The reagent is selected from the group consisting of: cotton brown belt moth granulosis virus ( Adoxophyes orana GV) (alias) (12) + TX, Agrobacterium tumefaciens (alias) (13) + TX, predatory mites ( Amblyseius Spp.) (alias) (19) + TX, celery genus nuclear polyhedrosis virus ( Anagapha falcifera NPV) (alias) (28) + TX, Anagrus atomus (alias) (29) + TX, locust parasitic wasp ( Aphelinus abdominalis ) (alias) (33) + TX, cotton mistletoe bee ( Aphidius colemani ) (alias) (34) + TX, 蚜瘿 mosquito ( Autographa californica NPV) (alias) (35) + TX, Helicoverpa armigera nuclear polyhedrosis virus ( Bacillus firmus ) (alias) (38) + TX, strong bacillus ( Bacillus firmus ) (alias) (48) + TX, globulin ( Bacillus sphaericus Neide) (49)+TX, Bacillus thuringiensis ( Bacillus thuringiensis Berliner) (scientific name) (51) + TX, Bacillus thuringiensis ( Bacillus thuringiensis Subsp. Aizawai ) (scientific name) (51) + TX, Bacillus thuringiensis subspecies of Israel ( Bacillus thuringiensis Subsp. Israelensis ) (scientific name) (51) + TX, Bacillus thuringiensis subsp. Bacillus thuringiensis Subsp. Japonensis ) (scientific name) (51) + TX, Bacillus thuringiensis k. ( Bacillus thuringiensis Subsp. Kurstaki ) (scientific name) (51) + TX, Bacillus thuringiensis t. ( Bacillus thurin-giensis Subsp. Tenebrionis ) (scientific name) (51) + TX, Beauveria bassiana ( Beauveria bassiana ) (alias) (53) + TX, Beauveria bassiana ( Beauveria brongniartii ) (alias) (54) + TX, grasshopper ( Chrysoperla carnea ) (alias) (151) + TX, Meng's hidden ladybug ( Cryptolaemus montrouzieri ) (alias) (178) + TX, Cocoon granule virus ( Cydia pomonella GV) (alias) (191) + TX, the first level of Lia Dacnusa sibirica ) (alias) (212) + TX, pea leaf miner Diglyphus isaea ) (alias) (254) + TX, Li Wei wasp ( Encarsia formosa ) (scientific name) (293) + TX, paddle horned bee ( Eretmocerus eremicus ) (alias) (300) + TX, Helicoverpa armigera nuclear polyhedrosis virus ( Helicoverpa zea ) (alias) (431) + TX, Helminthosporium elegans ( Heterorhabditis bacteriophora ) and H.megidis (alias) (433) + TX, converging long-legged ladybugs ( Hippodamia convergens ) (alias) (442) + TX, orange powder scale parasitic wasp ( Leptomastix dactylopii ) (alias) (488) + TX, blind 蝽 ( Macrolophus caliginosus ) (alias) (491) + TX, Brassica californica nuclear polyhedrosis virus ( Mamestra brassicae NPV) (alias) (494) + TX, Metaphycus helvolus (alias) (522)+TX, Metarhizium anisopliae ( Metarhizium anisopliae Var. Acridum (Scientific name) (523) + TX, Metarhizium anisopliae spores ( Metarhizium anisopliae Var. Anisopliae ) (scientific name) (523) + TX, pine yellow leaf bee ( Neodiprion sertifer Nuclear polyhedrosis virus and red-headed pine bee ( N.lecontei Nuclear polyhedrosis virus (alias) (575) + TX, small flower bud (alias) (596) + TX, Paecilomyces fuliginea ( Paecilomyces fumosoroseus ) (alias) (613) + TX, Pasteurella pneumoniae + TX, Pseudomonas aeruginosa ( Pasteuria thornei )+TX, Pasteuria nishizawae +TX, Pasteurella multocida + TX, Chilean plantation 螨 ( Phytoseiulus persimilis ) (alias) (644) + TX, beet armyworm ( Spodoptera exigua Multicapsid) multinuclear capsid nuclear polyhedrosis virus (scientific name) (741) + TX, hairy mosquito nematode ( Steinernema bibionis ) (alias) (742) + TX, M. elegans ( Steinernema feltiae ) (alias) (742) + TX, Spodoptera frugiperda (alias) (742) + TX, Steinernema glaseri (alias) (742) + TX, Steinernema riobrave (alias) (742) + TX, Steinernema riobravis (alias) (742) + TX, Steinernema scapterisci (alias) (742) + TX, Streptomyces elegans ( Steinernema Spp.) (alias) (742) + TX, Trichogramma (alias) (826) + TX, Western blind walk ( Typhlodromus occidentalis ) (alias) (844) and Verticillium lecanii ( Verticillium lecanii (alias) (848) + TX, soil disinfectant, the soil disinfectant is selected from the group consisting of methyl iodide (IUPAC name) (542) and methyl bromide (537) + TX, chemical disinfectant, the chemical disinfection The agent is selected from the group consisting of apholate [CCN] + TX, bisazir (alias) [CCN] + TX, busulfan (alias) [CCN] + TX, diflubenzuron (250) + TX, dimatif (alias) [CCN]+TX, hemel melamine [CCN]+TX, hexamethylphosphorus (hempa)[CCN]+TX, metepa[CCN]+TX, methyl sulphide Methiotepa [CCN]+TX, methyl apholate [CCN]+TX, grozid[CCN]+TX, penfluron (alias)[CCN]+TX , tepa [CCN]+TX, thiohempa (alias) [CCN]+TX, thiobarium (alias) [CCN]+TX, andramine (alias) [CCN] and Urinary imine (alias) [CCN]+TX, insect pheromones, selected from the group consisting of: E )-癸-5-en-1-yl acetate with E )-癸-5-en-1-ol (IUPAC name) (222)+TX, ( E )-Tridec-4-en-1-yl acetate (IUPAC name) (829) + TX, ( E )-6-methylhept-2-en-4-ol (IUPAC name) (541) + TX, ( E, Z )-tetradec-4,10-dien-1-yl acetate (IUPAC name) (779)+TX, ( Z )-Dodecyl-7-en-1-yl acetate (IUPAC name) (285) + TX, ( Z )-hexadecyl-11-enal (IUPAC name) (436) + TX, ( Z )-hexadecyl-11-en-1-yl acetate (IUPAC name) (437) + TX, ( Z )-hexadecyl-13-ene-11-yn-1-yl acetate (IUPAC name) (438) + TX, ( Z )-Tetra-13-en-1-one (IUPAC name) (448) + TX, (Z)-tetradec-7-en-1-al (IUPAC name) (782) + TX, ( Z )-tetradec-9-en-1-ol (IUPAC name) (783) + TX, (Z)-tetradec-9-en-1-yl acetate (IUPAC name) (784) + TX , (7 E ,9 Z )-Dodecyl-7,9-dien-1-yl acetate (IUPAC name) (283)+TX, (9 Z ,11 E )-tetradecyl-9,11-dien-1-yl acetate (IUPAC name) (780)+TX, (9 Z , 12 E - Fourteen carbon-9,12-dien-1-yl acetate (IUPAC name) (781) + TX, 14-methyl octadec-1-ene (IUPAC name) (545) + TX, 4 -Methyl hydrazine-5-ol and 4-methylindole-5-one (IUPAC name) (544)+TX, α-multistriatin (alias) [CCN]+TX, western pine scorpion pheromone (brevicomin) (alias) [CCN]+TX, dodecadienol (codlelure) (alias) [CCN]+TX, dodecadienyl (codlemone) (alias) (167)+TX, ketel (alias) (179)+TX, diseptlure (277)+TX, dodecano-8-en-1-yl acetate (IUPAC name) (286)+TX, twelve carbon -9-En-1-yl acetate (IUPAC name) (287) + TX, dodecene-8+TX, 10-dien-1-yl acetate (IUPAC name) (284) + TX, Dominicalure (alias) [CCN] + TX, 4-methyl octanoate (IUPAC name) (317) + TX, eugenol (alias) [CCN] + TX, southern pine 蠹 资讯 informational (frontalin) (alias ) [CCN] + TX, gossyplure (alias) (420) + TX, polydure (grandure) (421) + TX, trapping olefin mixture I (alias) (421) + TX , trapping olefin mixed II (alias) (421) + TX, trapping olefin mixed III (alias) (421) + TX, trapping olefin mixed IV (alias) (421) + TX, vinegar Hexadelide [CCN] + TX, ipsdienol (alias) [CCN] + TX, ipsenol (alias) [CCN] + TX, scarabure (alias) (481) + TX, Lineatin (alias) [CCN] + TX, litlure (alias) [CCN] + TX, looplure (alias) [CCN] + TX, medlure [CCN] + TX, megatomoic acid (alias) [CCN] + TX, trap Ether (methyl eugenol) (alias) (540) + TX, muscalure (563) + TX, octa-2,13-dien-1-yl acetate (IUPAC name) (588) + TX, octadec-3,13-dien-1-yl acetate (IUPAC name) (589)+TX, orfralure (alias) [CCN]+TX, oryctalure (alias) (317) +TX, erramone (alias) [CCN]+TX, siglure [CCN]+TX, sordidin (alias) (736)+TX, sulcatol (alias)[CCN]+TX, Fourteen 11-en-1-yl acetate (IUPAC name) (785) + TX, special ketone (839) + TX, special ketone A (alias) (839) + TX, special ketone B ₁ (alias) (839) + TX, special ketone B ₂ (alias) (839) + TX, special estrone C (alias) (839) and trunc-call (alias) [CCN] + TX, an insect repellent selected from the group consisting of: 2-(octylthio)ethanol (IUPAC name) (591) + TX, butopyronoxyl (933) + TX, butoxy (polypropylene glycol) (936) + TX, dibutyl adipate (IUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (IUPAC name) (1048) + TX, DEET [CCN] + TX, mosquito repellent Dimethyl carbate [CCN]+TX, dimethyl phthalate [CCN]+TX, ethyl hexanediol (1137)+TX, hexamide[CCN]+TX, methoquin-butyl (1276) +TX, methylneodecanamide [CCN] + TX, oxamate (CCN) and picaridin [CCN] + TX, an insecticide selected from the group consisting of: 1- Dichloro-1-nitroethane (IUPAC/Chemical Abstracts Name) (1058) + TX, 1,1-Dichloro-2,2-bis(4-ethylphenyl)ethane (IUPAC name) (1056 +TX, 1,2-dichloropropane (IUPAC/Chemical Abstracts Name) (1062) + TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063) + TX , 1-bromo-2-chloroethane (IUPAC/Chemical Abstracts Name) (91 6) +TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate (IUPAC name) (1451) + TX, 2,2-dichlorovinyl 2- Ethyl sulfinium ethyl methyl phosphate (IUPAC name) (1066) + TX, 2-(1,3-dithiolan-2-yl) phenyl dimethyl carbamate (IUPAC) /Chemical Abstracts Name)(1109)+TX, 2-(2-butoxyethoxy)ethyl thiocyanate (IUPAC/Chemical Abstract) (935)+TX, methylaminocarbamate 2-( 4,5-Dimethyl-1,3-dioxocyclopentan-2-yl)phenyl ester (IUPAC/Chemical Abstracts Name) (1084)+TX, 2-(4-chloro-3,5-di Tolyloxy)ethanol (IUPAC name) (986) + TX, 2-chlorovinyl diethyl phosphate (IUPAC name) (984) + TX, 2-imidazolidinone (IUPAC name) (1225) + TX 2-isoamylindenylindoline-1,3-dione (IUPAC name) (1246)+TX, methylaminocarbamic acid 2-methyl(prop-2-ynyl)aminophenyl ester ( IUPAC name) (1284) + TX, 2-thiocyanatoethyl laurate (IUPAC name) (1433) + TX, 3-bromo-1-chloroprop-1-ene (IUPAC name) (917) + TX, 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate (IUPAC name) (1283) + TX, methylaminocarbamate 4-methyl (prop-2-ynyl) Amino-3,5-dimethylphenyl ester (IUPAC name) (1285)+TX, dimethylaminocarbamic acid 5,5-dimethyl-3-oxocyclohex-1-enyl ester (IUPAC name) (1085)+TX, avermectin (1 +TX, acetaminophen (2) + TX, acetamiprid (4) + TX, housefly phosphorus (alias) [CCN] + TX, acetaminophen [CCN] + TX, flumethrin (9) +TX, acrylonitrile (IUPAC name) (861) + TX, cotton ring (15) + TX, aldicarb (16) + TX, annihilation (863) + TX, chloromethalin ( 864) +TX, methrin (17) + TX, alomycin (alias) [CCN] + TX, chlorpyrifos (866) + TX, alpha-cypermethrin (202) + TX, alpha-skin Hormone (alias) [CCN]+TX, aluminum phosphide (640)+TX, thiophene (870)+TX, thioguanamine (872)+TX, chlorpyrifos (873)+TX, amine phosphorus (875) + TX, amine phosphinate (875) + TX, amitraz (24) + TX, neonicotinine (877) + TX, ethyl chlorpyrifos (883) + TX, AVI 382 ( Compound code) +TX, AZ 60541 (compound code) + TX, azadirachtin (alias) (41) + TX, pyridinium (42) + TX, azinphos-ethyl (44) + TX, valley Thioflavin-methyl (45)+TX, azophosphorus (889)+TX, Bacillus thuringiensis δ - endotoxin (alias) (52) + TX, hexafluoroantimonate (alias) [CCN] + TX, polysulfide (IUPAC / Chemical Abstracts) (892) + TX, fenvalerol [CCN] + TX, Bayer 22/190 (development code) (893) + TX, Bayer 22408 (development code) (894) + TX, worm (58) + TX, thiocarbamate (60) + TX, insecticide Sulfone (66)+TX, β-cyfluthrin (194)+TX, β-cypermethrin (203)+TX, bifenthrin (76)+TX, bio-methrin (78)+TX, bioallyl Pyrethroid S - cyclopentenyl isomer (alias) (79) + TX, bioethanomethrin [CCN] + TX, permethrin (908) + TX, pyrethrin (80) + TX, bis(2-chloroethyl)ether (IUPAC name) (909)+TX, bistrifluoroidazolium (83)+TX, borax (86)+TX, methrin (alias)+TX, bromine Phenylphosphine (914)+TX, bromoalkenyl (918)+TX, bromine-DDT (alias)[CCN]+TX, bromothion (920)+TX, bromothio-ethyl (921)+TX , Heweiwei (924) + TX, buprofezin (99) + TX, animal worm (926) + TX, butathiofos (927) + TX, butanone (103) + TX, butyl phosphine (932) +TX, butanone Converse (104) + TX, butyl hydrazine (alias) + TX, sulphur phosphorus (109) + TX, calcium arsenate [CCN] + TX, calcium cyanide (444) + TX , calcium polysulfide (IUPAC name) (111) + TX, toxaphene (941) + TX, chlorhexime (943) + TX, carbaryl (115) + TX, carbofuran (118) + TX, Carbon disulfide (IUPAC/Chemical Abstracts name) (945)+TX, carbon tetrachloride (IUPAC name) (946)+TX, trisulfide (947)+TX, butyl thiocarbene (119)+TX, killing Dan (123) + TX, chlorpyrifos hydrochloride (123) + TX, simvadine (alias) (725) + TX, borneol Dan (960) + TX, chlordane (128) + TX, cockroach ( 963) +TX, insecticide 964 (964) + TX, kill Bismuth hydrochloride (964) + TX, chlorophosphorus (129) + TX, chlorfenapyr (130) + TX, chlorpyrifos (131) + TX, worm (132) + TX, chloroform ( 136)+TX, chloroform [CCN]+TX, trichloronitromethane (141)+TX, chlorinated phos(989)+TX, chlorpyrifos (990)+TX, chlorpyrifos (145)+TX, chlorpyrifos -Methyl (146)+TX, chlorpyrifos (994)+TX, circumcision (150)+TX, cinerein I(696)+TX, cinerein II (696)+TX, cinerea Classes (696) + TX, cis-resmethrin (alias) + TX, cismethrin (80) + TX, fluvalinate (alias) + TX, Line (999)+TX, cyanoguanidin (alias) [CCN]+TX, clothianidin (165)+TX, copper arsenite arsenate [CCN]+TX, copper arsenate [CCN]+ TX, copper oleate [CCN]+TX, fly poisonous phosphorus (174)+TX, carnivorous phosphorus (1006)+TX, clomiphene (alias)[CCN]+TX, batophos (1010)+TX , ruthenium phosphate (1011) + TX, cryolite (alias) (177) + TX, CS 708 (development code) (1012) + TX, benzonitrile phosphine (1019) + TX, acaricidal nitrile (184) + TX, fruit worm phosphorus (1020) + TX, cyproterone [CCN] + TX, fenpropathrin (188) + TX, cyfluthrin (193) + TX, cyhalothrin (196) + TX , cypermethrin (201) + TX, phenyl cyanide Ester (206) + TX, cyromazine (209) + TX, phosphorus cattle tick (alias) [CCN] + TX, d - Limonene (alias) [CCN]+TX, d - tetramethrin (alias) (788) + TX, DAEP (1031) + TX, cotton (216) + TX, DDT (219) + TX, decarbofuran (1034) + TX, deltamethrin (223) +TX, Tianle Phosphorus (1037)+TX, Tianle Phosphorus-O(1037)+TX, Tianle Phosphorus-S(1037)+TX, Systemic Phosphorus (1038)+TX, Systematic Phosphorus-Methyl 224) +TX, inhaled phosphorus-O(1038)+TX, inhaled phosphorus-O-methyl (224)+TX, inhaled phosphorus-S(1038)+TX, and internally absorbed phosphorus-S-methyl ( 224) +TX, systemic phosphorus-S-methyl hydrazine (1039) + TX, dibutyl ether urea (226) + TX, chloroimidate (1042) + TX, diamine phosphorus (1044) + TX, two Pyriazine (227)+TX, isochlorophosphonate (1050)+TX, dephosphorization (1051)+TX, dichlorvos (236)+TX, dicliphos (alias)+TX, dicresyl (alias)[CCN]+TX, Dicrotophos (243)+TX, desfenil (244)+TX, dieldrin (1070)+TX, diethyl 5-methylpyrazol-3-yl phosphate (IUPAC name) (1076) +TX, diflubenzuron (250) + TX, dihydroxypropyl theophylline (dilor) (alias) [CCN] + TX, tetrafluthrin [CCN] + TX, methyl fluoride (1081) + TX, Dimai (1085)+TX, Dimethoate (262)+TX, methrin (1083)+TX, methyl chlorpyrifos (265)+TX, chlorpyrifos (1086)+TX, decylphenol ( 1089)+TX, decylphenol-diclexine (1089)+TX, propofol (1093)+TX, pent Phenol (1094)+TX, Danox (1095)+TX, dinotefuran (271)+TX, benzyl ether (1099)+TX, fruit and vegetable phosphorus (1100)+TX, dioxin (1101)+TX , Ethophos (1102) + TX, bismuth phosphorus (278) + TX, dithicrofos (1108) + TX, DNOC (282) + TX, doramectin (alias) [CCN] +TX, DSP (1115) + TX, ecdysone (alias) [CCN] + TX, EI 1642 (development code) (1118) + TX, methoxy avermectin (291) + TX, methoxy Vermicillin benzoate (291)+TX, EMPC(1120)+TX, enthrin (292)+TX, endosulfan (294)+TX, toxic phosphorus (1121)+TX, ende Agent (1122) + TX, EPBP (1123) + TX, EPN (297) + TX, juvenile ether (1124) + TX, erinoxine (alias) [CCN] + TX, fenvalerate ( 302) +TX, Oxfordshire thiophene (etaphos) (alias) [CCN] + TX, thiazol (308) + TX, ethion (309) + TX, ethiprole (310) + TX, Disulfide-methyl (1134)+TX, phosphazone (312)+TX, ethyl formate (IUPAC name) [CCN]+TX, ethyl-DDD (alias) (1056)+TX, dibromination Ethylene (316) + TX, ethylene dichloride (chemical name) (1136) + TX, ethylene oxide [CCN] + TX, ether methrin (319) + TX, pyrithione (1142) + TX, EXD (1143) + TX, ammonia sulfonate (3 23) +TX, benzene line phosphorus (326) + TX, anti-carbazole (1147) + TX, picophos (1148) + TX, phenylthiocarb (1149) + TX, fenfluramine (1150) + TX , chlorpyrifos (335) + TX, butyl benzo (336) + TX, fenoxacrim (1153) + TX, phenoxy (340) + TX, beta-cypermethrin (1155) + TX, Cypermethrin (342) + TX, pyridoxamine (alias) + TX, Fonsophos (1158) + TX, fenthion (346) + TX, fenthion-ethyl [CCN] + TX, fenvalerate (349) + TX, fipronil (354) + TX, fluramide (358) + TX, flubendiamide (CAS registration number: 272451-65-7) + TX, Flucofuron (1168) + TX, fluorocyclic urea (366) + TX, fluvalfenate (367) + TX, bisfluorene (1169) + TX, acetamiprid [CCN] + TX, flubendiamide (370 +TX, trifluthrin (1171) + TX, flumethrin (372) + TX, flupyradifurone + TX, fluvalinate (1184) + TX, FMC 1137 (development code) (1185) +TX, Phytophthora (1191)+TX, worm (405)+TX, worms (405)+TX, thiophene (1192)+TX, formparanate (1193) ) +TX, butyl thiophene (1194) + TX, formazin (1195) + TX, thiazolone phosphorus (408) + TX, butyl thiophosphorus (1196) + TX, furosemide (412) + TX , insect-resistant chrysanthemum (1200 +TX, γ-cyhalothrin (197)+TX, γ-HCH(430)+TX, biguanide salt (422)+TX, biguanide acetate (422)+TX, GY-81 (development code) (423)+TX, benzal ether (424)+TX, chlorantranil (425)+TX, HCH(430)+TX, HEOD(1070)+TX, febda (1211)+TX, heptene Phosphorus (432)+TX, chlorfenapyr [CCN]+TX, hexaflumuron (439)+TX, HHDN(864)+TX, fluoroantimony (443)+TX, hydrocyanic acid (444)+TX , olefin ethyl ester (445) + TX, hyquincarb (1223) + TX, imidacloprid (458) + TX, methadin (460) + TX, indoxacarb (465) + TX, methyl iodide (IUPAC name) (542)+TX, IPSP(1229)+TX, chlorpyrifos (1231)+TX, carbochlorin (1232)+TX, acesulfame (alias) (473)+TX, iso-acet (1235) ) +TX, iso-phosphorus (1236) + TX, transplanted spirit (1237) + TX, isoprocarb (472) + TX, O -(Methoxyaminothiophosphonium) isopropyl salicylate (IUPAC name) (473)+TX, indigo (474)+TX, isophosphorus (1244)+TX, oxazoline (480)+TX, ivermectin (alias) [CCN]+TX, ketomethrin I (696)+TX, ketomethrin II (696)+TX, iodophos (1248)+TX, Juvenile hormone I (alias) [CCN]+TX, juvenile hormone II (alias) [CCN]+TX, juvenile hormone III (alias) [CCN]+TX, chloropentane (1249)+TX, olefin Alkyne ester (484)+TX, γ-cyhalothrin (198)+TX, lead arsenate [CCN]+TX, phagecin (CCN)+TX, p-bromophosphonate (1250)+TX, Lindane (430)+TX, lirimfos (1251)+TX, guanidinium (490)+TX, thiazolyl (1253)+TX, m-isopropylphenylmethylcarbamate (IUPAC name) 1014) +TX, magnesium phosphide (IUPAC name) (640) + TX, malathion (492) + TX, terpene nitrile (1254) + TX, azide phosphorus (1255) + TX, bismuth phosphorus ( 502) +TX, tetramethylphosphorus (1258) + TX, thiophene (1260) + TX, diammine (1261) + TX, mercuric chloride (513) + TX, mesulfenfos (1263) + TX, Cyhalothrin (CCN) + TX, Weibaimu (519) + TX, Weibaimu potassium (alias) (519) + TX, Weibaimu sodium (519) + TX, insects (1266) + TX , methamidophos (527) + TX, methyl sulfonium chloride (I UPAC/Chemical Abstracts Name) (1268)+TX, chlorpyrifos (529)+TX, chlorpyrifos (530)+TX, insecticidal ethylene phosphorus (1273)+TX, methomyl (531)+TX, olefin Ester (532) + TX, mequitine (1276) + TX, methotrexate (alias) (533) + TX, methoxy drop (534) + TX, methoxybenzoquinone (535) + TX, methyl bromide ( 537) +TX, methyl isothiocyanate (543) + TX, methyl chloroform (alias) [CCN] + TX, dichloromethane [CCN] + TX, trimethoprim [CCN] + TX, Kuweiwei (550) + TX, trichlorfon (1288) + TX, fast-acting phosphorus (556) + TX, Zwicki (1290) + TX, metostatin (557) + TX, milbemycin ( Alias) [CCN] + TX, propylamine fluoride (1293) + TX, mirex (1294) + TX, monocrotophos (561) + TX, phosphos (1300) + TX, moxidectin (alias )[CCN]+TX, naphthoquinone phosphorus (alias) [CCN]+TX, dibromophosphorus (567)+TX, naphthalene (IUPAC/Chemical Abstracts) (1303)+TX, NC-170 (development code) 1306) +TX, NC-184 (compound code) + TX, nicotine (578) + TX, nicotine sulfate (578) + TX, flu urin (1309) + TX, nitenpyram (579) + TX , nithiazine (1311) + TX, pentamidine (1313) + TX, pentamidine 1:1 zinc chloride complex (1313) + TX, NNI-0101 (compound code) + TX NN I-0250 (compound code) + TX, nornicotine (traditional name) (1319) + TX, diphenylfluorourea (585) + TX, polyfluorourea (586) + TX, O -5-dichloro-4-iodophenyl O -ethylethylphosphonothioate (IUPAC name) (1057) + TX, O, O -diethyl O -4-methyl-2-oxo-2 H - Iso-7-yl phosphorothioate (IUPAC name) (1074) + TX, O, O -diethyl O -6-methyl-2-propylpyrimidin-4-yl thiophosphate (IUPAC name) (1075) + TX, O, O, O ' , O '-tetrapropyl dithio pyrophosphate (IUPAC name) (1424) + TX, oleic acid (IUPAC name) (593) + TX, omethoate (594) + TX, kill line (602) + TX , sputum phosphorus-methyl (609) + TX, iso-p-phosphonium (1324) + TX, argon phosphorus (1325) + TX, pp'-DDT (219) + TX, p-dichlorobenzene [CCN] +TX, parathion (615)+TX, parathion-methyl (616)+TX, fluorojumolone (alias) [CCN]+TX, pentachlorophenol (623)+TX, pentachlorobenzene laurate Base ester (IUPAC name) (623) + TX, permethrin (626) + TX, petroleum oil (alias) (628) + TX, PH 60-38 (development code) (1328) + TX, fenthion (1330)+TX, phenethrin (630)+TX, Daofengsan (631)+TX, phorate (636)+TX, sulforaphane (637)+TX, thiocyclophosphorus (1338) +TX, imipenem (638) + TX, parathion (1339) + TX, phosphonium (639) + TX, phosphine (IUPAC name) (640) + TX, phoxim (642) + TX , phoxim-methyl (1340)+TX, pirimetaphos (1344)+TX, anti-蚜威(651)+TX, worm-phosphonium-ethyl (1345)+TX, worm-phosphorus-methyl (652) +TX, polychlorodicyclopentadiene isomer (IUPAC name) (1346) + TX, polychlorinated (traditional name) (1347) + TX, potassium arsenite [CCN] + TX, thiocyanate Potassium acid [CCN]+TX, propythrin ( 655) + TX, precocious I (alias) [CCN] + TX, precocious II (alias) [CCN] + TX, precocious III (alias) [CCN] + TX, primidophos (1349) ) +TX, profenofos (662) + TX, fipronil [CCN] + TX, Converse (1354) + TX, Mengwei (1355) + TX, chlorpyrifos (1356) + TX, Acetophenone (673) + TX, propoxur (678) + TX, ethiazole (1360) + TX, propionate (686) + TX, thiophene (1362) + TX, protrifenbute [CCN] + TX , pymetrozine (688) + TX, pyrazophos (689) + TX, fixed phosphorus (693) + TX, pyresmethrin (1367) + TX, pyrethrin I (696) + TX, pyrethrum Ester II (696) + TX, pyrethrins (696) + TX, 哒螨 ( (699) + TX, acetamiprid (700) + TX, 嗒 Phosphorus (701)+TX, pyridoxine (706)+TX, pyrisulfuron (1370)+TX, pyriproxyfen (708)+TX, quassia (alias)[CCN]+TX Quinphophos (711)+TX, quetiapine-methyl (1376)+TX, sulphonium (1380)+TX, quintiofos (1381)+TX, R-1492 ( Development code) (1382) + TX, Rafanet (alias) [CCN] + TX, fenfenyl (719) + TX, rotenone (722) + TX, RU 15525 (development code) (723) + TX , RU 25475 (development code) (1386) + TX, Nyna (ryania) (alias) (1387) + TX, Liannod (traditional name) (1387) + TX, Sabah Gourd (alias) (725 ) +TX, octaphosphorus (1389) + TX, sulphur phosphorus (alias) + TX, serramycin (alias) [CCN] + TX, SI-0009 (compound code) + TX, SI-0205 (compound) Code) +TX, SI-0404 (compound code) + TX, SI-0405 (compound code) + TX, flumethrin (728) + TX, SN 72129 (development code) (1397) + TX, arsenic acid Sodium [CCN]+TX, sodium cyanide (444)+TX, sodium fluoride (IUPAC/Chemical Abstracts) (1399)+TX, sodium hexafluoroantimonate (1400)+TX, sodium pentachlorophenolate (623) +TX, sodium selenate (IUPAC name) (1401) + TX, sodium thiocyanate [CCN] + TX, thiophosphorus (1402) + TX, spinosyn (73 7) +TX, spironolactone (739) + TX, spirotetramat [CCN] + TX, sulcofuron (746) + TX, sulcofuron-sodium (746) + TX, sulfluramid (750) + TX, Treatment of bismuth phosphorus (753) + TX, strontium sulfide (756) + TX, thiopropyl phosphorus (1408) + TX, tar (alias) (758) + TX, τ-fluurethane (398) + TX, thiazide (1412) + TX, TDE (1414) + TX, worm (762) + TX, pyridoxamine (763) + TX, butyl pyrimidine (764) + TX, fluorophenylurea ( 768) +TX, tefluthrin (769) + TX, dithiphos (770) + TX, TEPP (1417) + TX, cyclopentimeryl (1418) + TX, terbam (alias) + TX, Tetraphos (773) + TX, tetrachloroethane [CCN] + TX, insecticide (777) + TX, tetramethrin (787) + TX, θ-cypermethrin (204) + TX, worm Porphyrin (791)+TX, thiafenox (alias)+TX, thiamethoxam (792)+TX, thicrofos (1428)+TX, clavirin (1431)+TX, insecticidal ring (798)+TX, insecticidal Hydroxyl hydrogen oxalate (798)+TX, thiodicarb (799)+TX, Jiuweiwei (800)+TX, methyl ethoxide (801)+TX, insect line phosphorus (1434)+TX, insecticidal Thiosultap (803) + TX, thiosultap-sodium (803) + TX, sulphate (alias) [CCN] + TX, oxazolamide (809) + TX, tetramethrin ( 812) +TX, tetrafluthrin (81 3) +TX, transpermethrin (1440) + TX, probiotics (1441) + TX, oxazolidine (818) + TX, triazophos (820) + TX, oxazide (alias) + TX, enemy hundred Insect (824) + TX, trichlormetaphos-3 (alias) [CCN] + TX, poisonous phosphine (1452) + TX, phosphorus oxychloride (1455) + TX, triflumuron (835) + TX, mixed kill Wei (840)+TX, enedisulfonyl ester (1459)+TX, quenching phosphorus (847)+TX, vaniliprole[CCN]+TX, cucurbitine (alias)(725)+TX, cucurbitine (alias ) (725) + TX, XMC (853) + TX, chlorpyrifos (854) + TX, YI-5302 (compound code) + TX, cyhalothrin (205) + TX, zetamethrin (alias) + TX, phosphorus Zinc (640) + TX, zolaprofos (1469), and ZXI 8901 (development code) (858) + TX, cyanocyanide [736994-63-19] + TX, chlorella Benzamidine [500008-45-7]+TX, oxazolidine [560121-52-0]+TX, butylated fluoro ester [400882-07-7]+TX, flufenicol [337458-27- 2]+TX, ethyl spinosyn [187166-40-1+187166-15-0]+TX, spirotetramat [203313-25-1]+TX, fluramide nitrile [946578-00- 3]+TX, flufiprole[704886-18-0]+TX, meperfluthrin[915288-13-0]+TX, tetrafluthrin [84937-88-2]+TX, molluscicide, the mollusc The agent is selected from the group consisting of bis(tributyltin) oxide (IUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, in addition to line ( Cloethocarb)(999)+TX, copper arsenite arsenate [CCN]+TX, copper sulfate (172)+TX, triphenyltin (347)+TX, iron phosphate (IUPAC name) (352)+TX, four Polyacetaldehyde (518)+TX, chlorhexidine (530)+TX, niclosamide (576)+TX, niclosamide ethanolamine salt (576)+TX, pentachlorophenol (623)+TX, five Sodium chlorophenate (623)+TX, tizimcarb (1412)+TX, thiodicarb (799)+TX, tributyltin oxide (913)+TX, snail-killing Trifenmorph (1454) + TX, trimethacarb (840) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyl hydroxide (IUPAC name) (347) + TX , pyriprol [394730-71-3] + TX, nematicide, the nematicide selected from the group consisting of AKD-3088 (compound code) + TX, 1,2-dibromo-3-chloropropane ( IUPAC/Chemical Abstracts) (1045) + TX, 1,2-dichloropropane (IUPAC / Chemical Abstracts) (1062) + TX, 1,2-dichloropropane and 1,3-dichloropropene (IUPAC name (1063)+TX, 1,3-dichloropropene (233)+TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide (IUPAC/Chemical Abstracts) (1065)+TX, 3 -(4-chlorophenyl)-5-methylrosine (IUPAC name) (980)+TX, 5-methyl-6-thio-1,3,5-thiadipine 3-yl acetic acid (IUPAC name) (1286) + TX, 6-prenylamino hydrazine (alias) (210) + TX, avermectin (1) + TX, acetaminophen [CCN] +TX, cotton ring (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, AZ 60541 (compound code) + TX, benclothiaz [CCN] + TX, benomyl (62) + TX, butylpyridaben (alias) + TX, cadium fos (109) + TX, carbofuran (118) + TX, carbon disulfide (945) + TX, D Thiocarbazone (119) + TX, chloropicrin (141) + TX, chlorpyrifos (145) + TX, cloethocarb (999) + TX, cytokinins (alias) (210) +TX, Mianlong (216)+TX, DBCP(1045)+TX, DCIP(218)+TX, dimidofafs(1044)+TX, dephosphorination (1051)+TX, dicliphos (alias)+TX , Dimethoate (262) + TX, Doramectin (alias) [CCN] + TX, ED Marking (291) + TX, ezetidine benzoate (291) + TX, erinochromin (alias )[CCN]+TX, sterilized phosphorus (312)+TX, dibromoethane (316)+TX, phenophos (326)+TX, pyridoxamine (alias)+TX, Fonsophos (fenpyrad) (1158) + TX, thiazolyl (fosthiazate) (408) + TX, thiosulfate (fosthietan) (119 6) +TX, furfural (alias) [CCN] + TX, GY-81 (development code) (423) + TX, fastophos [CCN] + TX, methyl iodide (IUPAC name) (542) +TX, isamidofos (1230) + TX, isazofos (1231) + TX, ivermectin (alias) [CCN] + TX, kinetin (alias) (210) + TX, A Mecarphon (1258)+TX, Weibaimu (519)+TX, Weibaimu Potassium Salt (alias) (519)+TX, Weibaimu sodium salt (519)+TX, methyl bromide (537) ) +TX, methyl isothiocyanate (543) + TX, milbemycin oxime (alias) [CCN] + TX, moxidectin (alias) [CCN] + TX, coccispice Spotted fungus Myrothecium verrucaria ) composition (alias) (565) + TX, NC-184 (compound code) + TX, chlorpyrifos (602) + TX, phorate (636) + TX, phosphonium (639) + TX, phosphorus worm Phosphate [CCN]+TX, sephafos (alias)+TX, selamectin (alias)[CCN]+TX, spinosyn (737)+TX, tertiary butyl Terbam (alias) + TX, terbufos (773) + TX, tetrachlorothiophene (IUPAC / Chemical Abstracts) (1422) + TX, thiaf enox (alias) + TX, insect line phosphorus ( Thionazin) (1434) + TX, triazophos (820) + TX, triazuron (alias) + TX, xylenol [CCN] + TX, YI-5302 (compound code) and zeatin (alias) ( 210) +TX, fluensulfone [318290-98-1] + TX, a nitrification inhibitor selected from the group consisting of potassium ethyl xanthate [CCN] and nitridyrin ( 580) + TX, a plant activator, the plant activator is selected from the group consisting of thiazolyl (6) + TX, thiadiazol-S-methyl (6) + TX, alkene Probenazole (658) and Giant knotweed ( Reynoutria sachalinensis) Extract (alias) (720) + TX, rodenticide, selected from the group consisting of 2-isoamylindoline-1,3-dione (IUPAC name) (1246) +TX, 4-(quin Oxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748)+TX, α-chlorohydrin [CCN]+TX, aluminum phosphide (640)+TX, Antuo(880)(antu)+TX , arsenic trioxide (882) + TX, cesium carbonate (891) + TX, bisthiosemi (912) + TX, bronomone (89) + TX, bromadiolone (91) + TX, bromine Murine amine (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorophacinone (140) + TX, vitamin d3 (alias) (850) + TX, chlorine Warfarin (1004) + TX, coumafuryl (1005) + TX, coumatetralyl (175) + TX, rat death (1009) + TX, difenacoum (246) ) +TX, difethialone (249) + TX, diphacinone (273) + TX, vitamin D2 (301) + TX, flocoumafen (357) + TX, fluoroacetamidine Amine ( arylacetamide) (379) + TX, flupropadine (1183) + TX, flurazepam hydrochloride (1183) + TX, γ-HCH (430) + TX, HCH (430) + TX, Hydrogen cyanide (444) + TX, methyl iodide (IUPAC name) (542) + TX, Lin Dan (430) + TX, magnesium phosphide (IUPAC name) (640) + TX, methyl bromide (537) + TX, mouse Norbormide (1318) + TX, phosacetim (1336) + TX, phosphine (IUPAC name) (640) + TX, phosphorus [CCN] + TX , pindone (1341) + TX, potassium arsenite [CCN] + TX, pyrinuron (1371) + TX, serranos (1390) + TX, arsenic acid Sodium [CCN]+TX, sodium cyanide (444)+TX, sodium fluoroacetate (735)+TX, strychnine (745)+TX, barium sulfate [CCN]+TX, warfarin (851) and phosphorus Zinc (640) + TX, synergist, the synergist is selected from the group consisting of 2-(2-butoxyethoxy)ethyl piperate (IUPAC name) (934) + TX , 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903)+TX, a bacterium having nerolitriol Green enol (alias) (324) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code) (296) + TX, piperonyl butoxide (649) + TX, Synergistic aldehyde (piprotal) (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesasmolin ( 1394) and Aachen (1406) + TX, animal repellent, the animal repellent is selected from the group consisting of ruthenium (32) + TX, chloralose (127) + TX, copper naphthenate [CCN]+TX, copper oxychloride (171)+TX, diazinon (227) +TX, dicyclopentadiene (chemical name) (1069)+TX, guazatine (422)+TX, biguanide acetate (422)+TX, chlorfenapyr (530)+TX, pyridin-4-amine (IUPAC name) (23)+TX , erion (804) + TX, trimethacarb (840) + TX, zinc naphthenate [CCN] and thiram (856) + TX, viricide, the viricide is selected from the following substances Group: imanin (alias) [CCN] and ribavirin (alias) [CCN]+TX, a wound protectant selected from the group consisting of: oxidized mercury (512) +TX, octylinone (590) and thiophanate-methyl (802) + TX, and a biologically active compound selected from the group consisting of azaconazole (60207-31-0) +TX, biphenyl triazole alcohol [70585-36-3] + TX, carbendazole [116255-48-2] + TX, cyproconazole [94361-06-5] + TX, difenoconazole [119446-68-3]+TX, diniconol [83657-24-3]+TX, epoxicon-azole [106325-08-0]+TX, nitrile azole [114369-43-6 ]+TX, fluoroquinazole [136426-54-5]+TX, flucarbazole [85509-19-9]+TX, fluconazole [76674-21-0]+TX, hexaconazole [79983-71] -4]+TX, imazalil [35554-44-0]+TX, imidazole [86598-92-7]+TX, inoconazole [125225-28-7]+TX, meconazole [125116-23-6]+TX, myclobutanil [88671-89-0]+TX, rice glutamate [101903-30-4]+TX, pent Pyrazole [66246-88-6]+TX, prothioconazole [178928-70-6]+TX, pyrifenox [88283-41-4]+TX, prochloraz [67747-09- 5]+TX, propiconazole [60207-90-1]+TX, simeconazole [149508-90-7]+TX, tebuconazole [107534-96-3]+TX, fluoroetherazole [112281-77-3]+TX, triazolone [43121-43-3]+TX, triazolone [55219-65-3]+TX, fluconazole [99387-89-0]+TX, sterilization Azole [131983-72-7]+TX, tricyclobenzimidazole [12771-68-5]+TX, chloropyrimidinol [60168-88-9]+TX, chlorochloropyrimidinol [63284-71- 9]+TX, acetaminophen sulfonate (bupirimate) [41483-43-6]+TX, dimethirimol [5221-53-4]+TX, ethirimol [23947-60] -6]+TX, twelve rings Porphyrin [1593-77-7]+TX, fenpropidine [67306-00-7]+TX, butylbenzene Porphyrin [67564-91-4]+TX, spirocyclam [118134-30-8]+TX, thirteen Porphyrin [81412-43-3]+TX, cyprodinil [121552-61-2]+TX, azoxystrobin [110235-47-7]+TX, pyrimethanil (pyrimethanil) [53112-28-0 ]+TX, seed dressing [74738-17-3]+TX, fludioxonil [131341-86-1]+TX, benoxaxyl [71626-11-4]+TX, fur Furylaxyl [57646-30-7]+TX, metalaxyl [57837-19-1]+TX, R-metalaxyl [70630-17-0]+TX, furosemide [58810-48] -3]+TX, Oxadixyl[77732-09-3]+TX, benomyl [17804-35-2]+TX, carbendazim [10605-21-7]+TX, Bacillus Debacarb [62732-91-6]+TX, Mai Suining [3878-19-1]+TX, thiabendazole [148-79-8]+TX, chlozolinate [84332- 86-5] +TX, sclerotin (dichlozoline) [24201-58-9] + TX, Iprodione [36734-19-7] + TX, myclozoline [54864-61-8] + TX, Procymidone [32809-16-8]+TX, vinclozoline [50471-44-8]+TX, boscalid [188425-85-6]+TX, Brucea [5234-68-4]+TX, toluidine aniline [24691-80-3]+TX, fludroline (Flutolanil) [66332-96-5]+TX, rust-free amine [55814-41 -0]+TX, oxidized rust rust [5259-88-1]+TX, penthiopyrad (penthiopyrad) [183675-82 -3]+TX, cefotaxime [130000-40-7]+TX, biguanide salt [108173-90-6]+TX, dodine (2439-10-3)[112-65- 2] (free base) + TX, dioctyl octylamine (iminoctadine) [13516-27-3] + TX, azoxystrobin [131860-33-8] + TX, ethenamide [149961-52-4] + TX , enestrobin {Proc. BCPC, Int. Congr., Glasgow. 2003, 1, 93} + TX, fluoxastrobin [361377-29-9] + TX methyl oxystrobin [143390-89-0 ] +TX, phenoxystrobin [133408-50-1] + TX, trifloxystrobin [141517-21-7] + TX, epothilone [248593-16-0] + TX, picoxystrobin [ 117428-22-5]+TX, pyraclostrobin [175013-18-0]+TX, melamine iron [14484-64-1]+TX, mancozeb [8018-01-7]+TX, generation Sen Manganese [12427-38-2]+TX, Daisenlian [9006-42-2]+TX, propeneb [12071-83-9]+TX, Celen [137-26-8 ]+TX, Desen Zinc [12122-67-7]+TX, Fumex Zinc [137-30-4]+TX, Captafol [2425-06-1]+TX, Captan [133] -06-2]+TX, phenylsulfonamide [1085-98-9]+TX, oxaimide (41205-21-4)+TX, sterilized Dan [133-07-3]+TX, toluene Fluorosulfonamide [731-27-1] + TX, bordeaux mixture [8011-63-0] + TX, copper hydroxide (copperhydroxid) [20427-59-2] + TX, oxygen Copper oxychloride (1332-40-7)+TX, copper sulphate (7758-98-7)+TX, copper oxide (1317-39-1)+TX, mancozeb ( Mancopper)[53988-93-5]+TX, oxine-copper [10380-28-6]+TX, dinocap [131-72-6]+TX, trifloxystrobin ( Nitrothal-isopropyl)[10552-74-6]+TX, 克瘟散[17109-49-8]+TX, iprobenphos[26087-47-8]+TX, inoprothiolane [50512-35-1]+TX, phosdiphen [36519-00-3]+TX, pyrazophos [13457-18-6]+TX, methyltoluphos (tolclofos- Methyl)[57018-04-9]+TX, benzothiadiazole (acibenzo-lar-S-methyl)[135158-54-2]+TX, carbendazim [101-05-3]+TX, benzene Thiamin [413615-35-7]+TX, blasticidin-S[2079-00-7]+TX, chinomethio-nat [2439-01-2]+TX, ground Chloroneb [2675-77-6]+TX, chlorothalonil [1897-45-6] +TX, cycloflufenamide [180409-60-3] +TX, cymoxanil [57966-95-7] +TX, diclofenac (dichlone) [ 117-80-6] +TX, diclocymet [139920-32-4]+TX, diclomezine [ 62865-36-5] +TX, chloramine (dicloran) [99-30-9] +TX, metebutencarb [87130-20-9] +TX, olefin Porphyrin [110488-70-5] +TX, SYP-LI90 (Flumorph) [211867-47-9] +TX, dithianon [3347-22-6] +TX, ethaboxam (ethaboxam) [162650-77-3] +TX, etridiazole [2593-15-9] +TX, famoxadone [131807-57-3]+TX , fenamidone [161326-34-7] +TX, rice decylamine (Fenoxanil) [115852-48-7] +TX, triphenyltin (fentin) [668-34-8] +TX, azoxystrobin (ferimzone) [89269-64-7] +TX, fluazinam [79622-59-6] +TX, fluopicolide [239110-15-7] + TX, flusulfamide [106917-52-6] + TX, cyclosporin [126833-17-8] + TX, Fosetyl-aluminium [39148-24-8]+TX, hymexazol [10004-44-1]+TX, propidium zinc [140923-17-7]+TX, IKF-916 (Cyazofamid) [ 120116-88-3] +TX, kasugamycin [6980-18-3] + TX, mesasulfocarb [ 66952-49-6] +TX, benomyl [ 220899-03-6] +TX, pencycuron [pencycuron] 66063-05-6] +TX, benzoquinone [27355-22-2]+TX, polyoxins (11113-80-7)+TX, pramycin (probenazole) [27605-76-1]+TX, Baiwei Propamocarb[25606-41-1]+TX, proquinazid [189278-12-4]+TX, pyroquilon [57369-32-1]+TX, quinoxaline [124495-18-7]+TX, pentachloronitrobenzene [82-68-8]+TX, sulfur [7704-34-9]+TX, thiabendamine [223580-51-6]+TX, imidazole Triazoxide [72459-58-6]+TX, tricyclazole [41814-78-2]+TX, oxazinamide [26644-46-2]+TX, availablemycin [37248-47-8] +TX, zoxamide (RH7281) [156052-68-5] + TX, dipropargylamine [374726-62-2] + TX, pyridone (isopyrazam) [881685- 58-1]+TX, sedaxane [874967-67-6]+TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (9-dichloromethylene-1, 2,3,4-Tetrahydro-1,4-methyl bridge-naphthalen-5-yl)-decylamine (disclosed in WO 2007/048556) +TX, 3-difluoromethyl-1-methyl- 1H-pyrazole-4-carboxylic acid [2-(2,4-dichlorophenyl)-2-methoxy-1-methyl-ethyl]-decylamine (disclosed in WO 2008/148570) +TX, 1-[4-[4-[(5S)5-(2,6-difluorophenyl)-4,5-dihydro-1,2- Zyrid-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl Ethylketone+TX, 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2- Zyrid-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl Ethyl ketone [1003318-67-9], both of which are disclosed in WO 2010/123791, WO 2008/013925, WO 2008/013622, and WO 2011/051243, page 20)) +TX, and 3-difluoromethyl 1-Methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-diphenyl-2-yl)-guanamine (disclosed in WO 2006/087343) + TX.

References in square brackets after the active ingredient, for example [3878-19-1] , refer to the Chemical Abstracts Registration Number. The hybrid counterparts described above are known. The active ingredients are included in the Pesticide Manual [The Pesticide Manual-A World Compendium; 13th edition; editor: CDS Tomlin (CDSTomLin); UK Crop Protection Board], which are described above for the number of specific compounds in parentheses; for example, the compound "abamidin" is described by the number (1). When the above specific compound is added to "[CCN]", the compounds in question are included in the "Compendium of Pesticide Common Names" which is available on the Internet: [A. Wood The generic name for killing biocides, copyright © 1995-2004]; for example, the compound "acetoxonitrile" is described on the Internet at http://www.alanwood.net/pesticides/acetoptole.htmL. .

Most of the above-mentioned active ingredients are mentioned above by the so-called "common name", the related "ISO common name" or another "common name" used in individual cases. If the name is not "common name", it is used as a substitute for specific compounds in parentheses. The nature of the name; in this case, use the IUPAC name, IUPAC/Chemical Abstract Name, "Chemical Name", "Traditional Name", "Compound Name", or "Development Code", or if neither of these names are used One, and does not use "common name", it uses "alias". The "CAS registration number" indicates the chemical abstract registration number.

The mass ratio of any two components in each combination is selected to give the desired, e.g., synergistic effect. In general, this mass ratio will vary depending on the particular ingredients and how many ingredients are present in the combination. In general, the mass ratio between any two components in any combination of the invention is from 100:1 to 1:100 independently, including from 99:1, 98:2, 97:3, 96:4, 95:5, 94:6, 93:7, 92:8, 91:9, 90:10, 89:11, 88:12, 87:13, 86:14, 85:15, 84:16, 83: 17, 82:18, 81:19, 80:20, 79:21, 78:22, 77:23, 76:24, 75:25, 74:26, 73:27, 72:28, 71:29, 70:30, 69:31, 68:32, 67:33, 66:34, 65:45, 64:46, 63:47, 62:48, 61:49, 60:40, 59:41, 58: 42, 57:43, 56:44, 55:45, 54:46, 53:47, 52:48, 51:49, 50:50, 49:51, 48:52, 47:53, 46:54, 45:55, 44:56, 43:57, 42:58, 41:59, 40:60, 39:61, 38:62, 37:63, 36:64, 35:65, 34:66, 33: 67, 32:68, 31:69, 30:70, 29:71, 28:72, 27:73, 26:74, 25:75, 24:76, 23:77, 22:78, 21:79, 20:80, 19:81, 18:82, 17:83, 16:84, 15:85, 14:86, 13:87, 12:88, 1 1:89, 10:90, 9:91, 8:92, 7:93, 6:94, 5:95, 4:96, 3:97, 2:98, to 1:99. A preferred mass ratio between any two components of the invention is from 75:1 to 1:75, more preferably from 50:1 to 1.50, especially from 25:1 to 1:25, advantageously 10 :1 to 1:10, such as 5:1 to 1:5, such as 1:3 to 3:1. Such mixing ratios are understood to include, on the one hand, by mass and, on the other hand, Mohrby.

Examples of methods of application of the compounds and compositions thereof for use in the present invention (i.e., methods for controlling pests/fungi in agriculture), spraying, spraying, powdering, brushing, seed dressing, spreading or watering - they It is chosen to suit the intended purpose of the dominant situation.

In agriculture, the preferred method of application is applied to the leaves of such plants (leaf application), it being possible to select the frequency and ratio of application to meet the pest/fungal infestation risk discussed. Alternatively, the active ingredient can be passed through the root system to the plant (systemic action) by applying the compound to the locus of the plants, for example by applying a liquid composition of the compound to the soil (by soaking) Or by applying the solid form of the compound in the form of granules to the soil (soil application). In the case of rice plants, such granules can be metered into flooded rice fields.

Typical application rates per hectare are generally from 1 g to 2000 g per hectare, especially from 10 g/ha to 1000 g/ha, preferably from 10 g/ha to 600 g/ha, such as 50 g/ha Up to 300 g/ha.

The compounds of the invention and compositions thereof are also suitable for protecting plant propagation material (e.g., seeds, such as fruits, tubers or kernels, or nursery plants) against pests of the above type. The propagation material can be treated with the above compounds prior to planting, for example the seeds can be treated prior to sowing. Alternatively, the compound can be applied to the seed kernel (coating) by impregnating the seed into the liquid composition or by applying a layer of the solid composition. When the propagation material is planted at the site of application, it is also possible to apply the compositions to the seed furrow, for example during the sowing. Such methods of treatment for plant propagation material and plant propagation materials thus treated are additional subject matter of the present invention. The typical treatment ratio will depend on the plant as well as the pest/fungus to be controlled and is usually between 1 and 200 grams per 100 kg of seed, preferably between 5 and 150 grams per 100 kg of seed, such as per 100 kg. Seeds are between 10 and 100 grams.

The term seed includes seeds as well as all kinds of plant propagules including, but not limited to, true seeds, cuttings, roots, grains, bulbs, fruits, roots, grains, rhizomes, cuts, shoots Cut strips and the like and in the preferred embodiment refer to true seeds.

The invention also includes seeds coated or treated with a compound of formula I and/or comprising a compound of formula I. The term "coated or treated and/or included" generally means that at the time of administration, the active ingredient is mostly on the surface of the seed, although more or less portions of the ingredient may penetrate into the seed material (depending on Method of application). When the seed product is (re)planted, it can absorb the active ingredient. In an embodiment, the invention enables a plant propagation material to which a compound of formula (I) is adhered. Furthermore, it thus makes it possible to use compositions comprising plant propagation material treated with a compound of formula (I).

Seed treatment includes all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed application, seed soaking, and seed granulation. Seed treatment application of a compound of formula (I) can be carried out by any known method such as spraying or by powdering the seed before or during sowing/planting.

Suitable target plants are especially cereals such as wheat, barley, rye, oats, rice, corn or sorghum; beets, such as sugar or fodder beet; fruits such as pome fruit, stone fruit or seedless fruits such as apples, pears, Plums, peaches, almonds, cherries or berries, such as strawberries, raspberries or blackberries; legumes such as beans, lentils, peas or soybeans; oil plants such as canola, mustard, poppy, olives, sunflower, coconut, ramie, Cocoa or groundnuts; melons such as pumpkin, cucumber or melon; fiber plants such as cotton, flax, hemp or jute; citrus fruits such as citrus, lemon, grape sleeves or red orange; vegetables such as spinach, lettuce , asparagus, cabbage, carrots, onions, tomatoes, potatoes or sweet peppers; eucalyptus, such as avocado, eucalyptus or camphor; and tobacco, Fruit, coffee, eggplant, sugar cane, tea, pepper, grapes, hops, plantain, latex plants and ornamental plants (such as flowers and lawn plants or turf).

In an embodiment, the plant is selected from the group consisting of cereals, corn, soybeans, rice, sugar cane, vegetables, and oilseed plants.

The term "plant" is understood to also include plants which have been transformed by the use of recombinant DNA techniques such that they are capable of synthesizing one or more selectively acting toxins, such as those known to be derived from toxin producing bacteria, especially those of the genus Bacillus. ,.

Toxins which can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus or Japanese beetles; or insecticidal proteins from Bacillus thuringiensis, such as delta-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2. Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or a plant-based insecticidal protein (Vip), such as Vip1, Vip2, Vip3 or Vip3A; or an insecticidal protein of a bacterial colony forming a nematode, such as a genus of the genus Bacillus or the genus Bacillus, such as luminescence Light bacillus, nematophagous pathogenic bacilli; toxins produced by animals such as saxitoxin, spider toxin, wasp toxin and other insect-specific neurotoxins; toxins produced by fungi, such as streptomyces; plant lectins such as peas Lectin, barley lectin or snowdrop lectin; lectin; protease inhibitors such as trypsin inhibitor, serine protease inhibitor, potato patatin, cysteine protease inhibitor, papain Inhibitors: ribosome inactivating proteins (RIP), such as ricin, corn-RIP, acacia, and loofah Saponin toxin protein or xenobiotics; steroid metabolism enzymes such as 3-hydroxysteroid oxidase, ecdysteroid UDP-glycosyltransferase, cholesterol oxidase, ecdysone inhibitor, HMG-COA-reductase Ion channel blockers such as sodium channel or calcium channel blockers, juvenile hormone esterase, diuretic hormone receptor, purine synthase, bibenzyl synthase, chitinase and glucanase.

In the context of the present invention, delta-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Ea2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), such as Vip1, Vip2, Vip3 or Vip3A, are understood to be apparently also These include mixed toxins, truncated toxins, and modified toxins. Mixed toxins are produced by recombination of new combinations of different regions of those proteins (see, for example, WO 02/15701). Truncated toxins such as the truncated Cry1Ab line are known. In the case of a modified toxin, one or more amino acids of the naturally occurring toxin are replaced. In this amino acid substitution, it is preferred to insert a non-naturally occurring protease recognition sequence into the toxin, for example in the case of Cry3A055, the cathepsin-G-recognition sequence is inserted into the Cry3A toxin (see WO 03/018810) .

Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073.

Methods for preparing such transgenic plants are known to those skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.

Toxins contained in transgenic plants make plants resistant to harmful insects. Such insects may be present in any insect taxonomic group, but are especially found in beetles (coleoptera), double-winged insects (Diptera), and butterflies (Lepidoptera).

Transgenic plant lines containing one or more genes encoding insecticide resistance and expression of one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (corn variety, expressing Cry1Ab toxin); YieldGard Rootworm® (corn variety, expressing Cry3Bb1 toxin); YieldGard Plus® (corn variety, expressing Cry1AB and Cry3Bb1 toxin); Starlink® (corn variety, expressing Cry9C toxin); Herculex I® (corn variety, expression of Cry1Fa2 toxin and enzyme phosphinothricin N-ethyl sulfonate to achieve tolerance to the herbicide glufosinate Transferase (PAT)); NuCOTN 33B® (cotton variety, expressing Cry1Ac toxin); Bollgard I® (cotton variety, expressing Cry1Ac toxin); Bollgard II® (cotton variety, expressing Cry1Ac and Cry2Ab toxin); VipCot® (cotton variety) , expressing Vip3A and Cry1Ab toxins; NewLeaf® (potato varieties, expressing Cry3A toxins); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant traits), Agrisure® CB Advantage (Bt11 corn glutinous (CB) traits), and Protecta ®.

Other examples of such transgenic plants are:

1. Bt11 corn from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified maize, by transgenic expression of the truncated Cry1Ab toxin, is resistant to attack by European corn borer (corn borer and pink stem borer). Bt11 maize also transgenicly expresses the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonium salt.

2. Bt176 corn from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified maize, by transgenic expression of Cry1Ab toxin, is resistant to attack by European corn borer (corn borer and pink stem borer). Bt176 maize also transgenicly expresses the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonium salt.

3. MIR604 corn from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. The insect-resistant corn is made by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.

4. MON 863 Corn , from Monsanto Europe SA, 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses the Cry3Bb1 toxin and is resistant to certain coleopteran insects.

5. IPC 531 cotton from Monsanto 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/ES/96/02.

6. 1507 Corn , from Pioneer Overseas Corporation Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C/NL/00/10. Genetically modified maize, expressing the protein Cry1F to achieve resistance to certain lepidopteran insects and expressing PAT protein to achieve tolerance to the herbicide glufosinate ammonium salt.

7. NK603×MON 810 corn from Monsanto, 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03. By hybridizing the genetically modified variety NK603 and MON810, it is composed of a conventionally cultivated hybrid corn variety. NK603×MON 810 maize transgene expression of the CP4 EPSPS protein obtained from Agrobacterium strain CP4, rendered resistant to the herbicide Roundup® (containing glyphosate), and the Cry1Ab toxin obtained from the B. colsulaceae subsp. It is resistant to certain lepidopteran insects, including European corn borer.

In general, the compounds of the invention are used in the form of compositions (e.g., formulations) comprising a carrier. The compounds of the present invention and compositions thereof can be used in various forms, such as aerosol spray cans, capsule suspensions, cold mist concentrates, dustable powders, emulsifiable concentrates, oil-in-water emulsions, oil bags Water emulsion, capsule granules, fine granules, flowable concentrate for seed treatment, gas (under pressure), gas generating products, granules, hot mist concentrate, large particles, micro granules, oil dispersible powder End-oil, oil-miscible flowable concentrates, oil-miscible liquids, pastes, plant rodlets, powders for dry seed treatment, seeds coated with pesticides, soluble concentrates, Soluble powder, solution for seed treatment, suspension concentrate (flowable concentrate), ultra low volume (ulv) liquor, ultra low volume (ulv) suspension, water dispersible granule or tablet, for pulp A water-dispersible powder, a water-soluble granule or tablet, a water-soluble powder for seed treatment, and a wettable powder.

The formulations typically comprise a liquid or solid carrier and, optionally, one or more conventional formulation auxiliaries, which may be solid or liquid auxiliaries, such as unepoxidized or epoxidized vegetable oils (eg, rings) Oxidized coconut oil, rapeseed oil or soybean oil), antifoaming agent (for example, emu oil), preservative, clay, inorganic compound, viscosity modifier, surfactant, binder and/or tackifier. The composition may further comprise a fertilizer, a micronutrient donor or other formulation that affects plant growth, and includes a compound comprising the invention and one or more other biologically active agents (eg, bactericides, fungicides, nematicides). , a combination of plant activators, acaricides and insecticides.

Accordingly, the present invention also provides compositions comprising a compound of the invention and an agronomic carrier, and optionally one or more conventional formulation auxiliaries.

The compositions are prepared in a manner known per se, in the absence of auxiliaries, for example by grinding, sieving and/or compacting the solid compounds of the invention and in the presence of at least one auxiliaries, for example by The compounds of the invention are intimately mixed and/or milled with this or such adjuvants. In the case of the solid compounds of the invention, the compounds are ground/milled to ensure a particular particle size. The methods for preparing such compositions, as well as the use of the compounds of the invention for preparing such compositions, are also subject matter of the present invention.

Examples of compositions for use in agriculture are emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersibles, direct sprayable or dilutable solutions, coatable pastes, diluted emulsions, soluble a powder, a dispersible powder, a wettable powder, a dust, a granule or an encapsulation in a polymeric substance, the compositions comprising at least one compound according to the invention and the type of composition being selected to be suitable for the intended purpose and Leading situation.

Suitable examples of liquid carriers based unhydrogenated or partially hydrogenated aromatic hydrocarbons, preferably the alkyl part is C ₈ to C _12, such as xylene mixtures, alkylated naphthalenes or tetrahydronaphthalene, aliphatic Or alicyclic hydrocarbons such as paraffin or cyclohexane, alcohols such as ethanol, propanol or butanol, ethylene glycol and their ethers and esters such as propylene glycol, dipropylene glycol ether, ethylene glycol or ethylene Alcohol monomethyl ether or hexanediol monoethyl ether, ketones such as cyclohexanone, isophorone or diacetone alcohol, strong polar solvent such as N-methylpyrrolidin-2-one, dimethyl hydrazine or N , N-dimethylformamide, water, unepoxidized or epoxidized vegetable oils such as unepoxidized or epoxidized rapeseed oil, castor oil, coconut oil or soybean oil and eucalyptus oil.

Examples of solid carriers for use in, for example, dusts and dispersible powders are typically ground natural minerals such as calcite, talc, kaolin, montmorillonite or attapulgite. In order to improve physical properties, it is also possible to add highly dispersed vermiculite or highly dispersed absorbent polymers. Suitable particulate adsorptive supports for the particles are porous, such as pumice, brick, sepiolite or bentonite, and suitable non-adsorptive support materials are calcite or sand. In addition, granulated materials of a large amount of inorganic or organic natural materials, in particular dolomite or pulverized plant residues, can be used.

Suitable surface-active compounds are nonionic, cationic and/or anionic surfactants or surfactant mixtures which have good emulsifying, dispersing and wetting properties depending on the type of active ingredient to be formulated. The surfactants mentioned below are only considered as examples; in the formulation A large number of other surfactants conventionally used in the field of materials and suitable in accordance with the present invention are described in the relevant literature.

Suitable nonionic surfactants, in particular, polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, polyglycol ether derivatives of saturated or unsaturated fatty acids or polyethylene glycols of alkylphenols a glycol ether derivative which may comprise from about 3 to about 30 glycol ether groups and from about 8 to about 20 carbon atoms or in the alkane in the (cyclo)aliphatic hydrocarbon group The alkyl portion of the phenol contains from about 6 to about 18 carbon atoms. Also suitable is with polypropylene glycol, ethylene diamine polypropylene glycol or alkyl polypropylene glycol (having from 1 to about 10 carbon atoms in the alkyl chain, and having from about 20 to about 250 glycol ether groups and about A water soluble polyethylene oxide adduct of from 10 to about 100 propylene glycol ether groups. Typically, the above compounds comprise from 1 to about 5 ethylene glycol units per propylene glycol unit. Examples which may be mentioned are nonylphenoxypolyethoxyethanol, castor oil polyglycol ether, polypropylene glycol/polyethylene oxide adduct, tributylphenoxypolyethoxyethanol, poly Ethylene glycol or octylphenoxypolyethoxyethanol. Also suitable are fatty acid esters of polyoxyethylene sorbitan such as polyoxyethylene sorbitan trioleate.

The cationic surfactants are especially (lower or halogenated) lower alkyl or hydroxyalkyl groups which generally have at least one alkyl group (about 8 to about 22 C atoms) as a substituent and as other substituents. Quaternary ammonium salt of benzyl. Preferably, the salts are in the form of halides, methyl sulfates or ethyl sulfates. Examples are stearic acid trimethylammonium chloride and benzyl bis(2-chloroethyl)ethylammonium bromide.

Examples of suitable anionic surfactants are water soluble soaps or water soluble synthetic surface active compounds. Examples of suitable soaps are the alkali metal, alkaline earth metal or (unsubstituted or substituted) ammonium salts of fatty acids having from about 10 to about 22 C atoms, such as oleic acid or stearic acid. A sodium or potassium salt of an acid or natural fatty acid mixture (available, for example, from coconut oil or tall oil); fatty acid methyl taurine must also be mentioned. More commonly, however, are synthetic surfactants, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylaryl sulfonates. Conventionally, the fatty sulfonates and fatty sulfates are present as alkali metal, alkaline earth metal or (substituted or unsubstituted) ammonium salts and they typically have an alkyl group of from about 8 to about 22 C atoms. Alkyl is also understood to include the alkyl portion of the indenyl group; examples which may be mentioned are the sodium or calcium salt of lignosulfonic acid, the sodium or calcium salt of lauryl sulfate or the fatty alcohol sulfuric acid prepared from natural fatty acids. A sodium or calcium salt of a mixture of ester salts. This group also includes sulfate and sulfonate salts of fatty alcohol/ethylene oxide adducts. The sulfonated benzimidazole derivatives are preferably fatty acid groups comprising 2 sulfonyl groups and from about 8 to about 22 C atoms. Examples of alkylarylsulfonates are sodium, calcium or triethanolammonium salts of mercaptobenzenesulfonic acid, dibutylnaphthalenesulfonic acid or naphthalenesulfonic acid/formaldehyde condensate. Further, it is also possible to use a suitable phosphate, such as a phosphonium salt of a p-nonylphenol/(4-14) ethylene oxide adduct, or a phospholipid.

Conventionally, the compositions comprise from 0.1% to 99%, in particular from 0.1% to 95%, of the compound according to the invention and from 1% to 99.9%, in particular from 5% to 99.9%, of at least one solid or liquid carrier It is in principle possible that from 0% to 25% (especially from 0.1% to 20%) of the composition is a surfactant (% in each case represents a weight percentage). For commercial applications, however, concentrated compositions are generally preferred, and end users in principle use diluted compositions having significantly lower concentrations of active ingredients. Preferred compositions are in particular composed as follows (% = weight percent): emulsifiable concentrate: active ingredient: 1% to 95%, preferably 5% to 20%

Surfactant: 1% to 30%, preferably 10% to 20%

Solvent: 5% to 98%, preferably 70% to 85%

Dust: active ingredient: 0.1% to 10%, preferably 0.1% to 1%

Solid carrier: 99.9% to 90%, preferably 99.9% to 99%

Suspension concentrate and flowable concentrate: active ingredient: 5% to 75%, preferably 10% to 50%

Water: 94% to 24%, preferably 88% to 30%

Surfactant: 1% to 40%, preferably 2% to 30%

Wettable powder: active ingredient: 0.5% to 90%, preferably 1% to 80%

Surfactant: 0.5% to 20%, preferably 1% to 15%

Solid carrier: 5% to 99%, preferably 15% to 98%

Granule: active ingredient: 0.5% to 30%, preferably 3% to 15%

Solid carrier: 99.5% to 70%, preferably 97% to 85%

Formulation example (%=% by weight)

Any desired concentration of emulsion can be prepared from such concentrates by dilution with water.

These solutions are suitable for use in the form of droplets.

The active ingredient is dissolved in dichloromethane, the solution is sprayed onto this or the support and the solvent is subsequently removed by evaporation under vacuum.

A ready-to-use dust is obtained by intimately mixing the carriers with the active ingredient.

The active ingredient is mixed with the additives and the mixture is thoroughly ground in a suitable mill. A wettable powder is obtained which can be diluted with water to give a suspension of any desired concentration.

The active ingredient is mixed with the additives and the mixture is ground, wetted with water, extruded, granulated, and dried in a stream of air.

The finely ground active ingredient is applied uniformly to the kaolin which has been wetted with polyethylene glycol in a mixer. A dust-free coated granule is obtained.

The finely ground active ingredient is intimately mixed with the additives. Any suspension of the desired concentration can be prepared by diluting from the suspension concentrate thus obtained with water.

The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill to obtain a powder that can be directly used for seed treatment.

An emulsion having any desired dilution which can be used in plant protection can be obtained from such concentrate by dilution with water.

This finely ground combination is intimately mixed with the adjuvants to give a suspension concentrate from which any desired dilution of the suspension can be obtained using water dilution. Using such dilutions, live plants can be treated along with plant propagation material and protected against microbial infestation by spraying, pouring or dipping. An example of a leaf formulation type for a premix composition is: GR: granules

WP: wettable powder

WG: water dispersible granules (powder)

SG: water soluble particles

SL: soluble concentrate

EC: emulsifiable concentrate

EW: lotion, oil-in-water

ME: Microemulsion

SC: Aqueous suspension concentrate

CS: aqueous capsule suspension

OD: oil-based suspension concentrate, and SE: aqueous suspoemulsion.

An example of a seed treatment formulation type for a premix composition is: WS: a wettable powder for seed treatment slurry

LS: solution for seed treatment

ES: lotion for seed treatment

FS: suspension concentrate for seed treatment

WG: water dispersible granules, and CS: aqueous capsule suspension.

Examples of types of formulations suitable for tank mix compositions are solutions, diluted emulsions, suspensions or mixtures thereof, and dusts.

For the nature of such formulations, methods of application, such as leaf, wet through, spray, atomization, powder application, spreading, coating or pouring, can be selected depending on the intended purpose and the prevailing environment.

The tank mix compositions are generally prepared by diluting one or more premix compositions containing different pesticidal agents and, optionally, additional auxiliaries, with a solvent (e.g., water).

Suitable carriers and adjuvants may be solid or liquid and are commonly used in formulation techniques, such as natural or regenerated mineral materials, solvents, dispersants, wetting agents, tackifiers, extenders, binders. Or fertilizers.

In general, tank mix formulations for leaf or soil application comprise from 0.1% to 20%, especially from 0.1% to 15%, of the desired ingredients, and from 99.9% to 80%, especially from 99.9% to 85% solids. Or a liquid adjuvant (including, for example, a solvent such as water), wherein the adjuvant may be a surfactant in an amount of from 0 to 20%, especially from 0.1% to 15%, based on the tank mix formulation.

Typically, the premix formulation for foliar application comprises from 0.1% to 99.9%, especially from 1% to 95%, of the desired ingredients, and from 99.9% to 0.1%, especially from 99% to 5% solids or liquids. Adjuvants (including, for example, solvents such as water), wherein the adjuvants may be surfactants in an amount of from 0 to 50%, especially from 0.5% to 40%, based on the premixed formulation.

Typically, the tank mix formulation for seed treatment application comprises from 0.25% to 80%, especially from 1% to 75%, of the desired ingredients, and from 99.75% to 20%, especially from 99% to 25% solids or liquids. Auxiliaries (including, for example, solvents such as water), wherein the auxiliaries may be surfactants in an amount of from 0 to 40%, especially from 0.5% to 30%, based on the tank mix formulation.

Typically, the premix formulation for seed treatment application comprises from 0.5% to 99.9%, especially from 1% to 95%, of the desired ingredients, and from 99.5% to 0.1%, especially from 99% to 5% solids or Liquid adjuvants (including, for example, solvents such as water), wherein the adjuvants may be surfactants in an amount of from 0 to 50%, especially from 0.5% to 40%, based on the premixed formulation.

Commercially available products are preferably formulated as concentrates (eg, premixed compositions (formulated) The end user typically uses a diluted formulation (eg, a tank mix composition).

A preferred seed treatment premix formulation is an aqueous suspension concentrate. The formulation can be applied to the seed using conventional processing techniques as well as machines such as fluidized bed techniques, barrel milling methods, rotostatic seed processors, and drum applicators. Other methods, such as a spray bed, can also be useful. The seeds can be presized prior to coating. After coating, the seeds are typically dried and then transferred to a sizing machine for coating. Such methods are well known in the art.

In general, the premix composition of the invention comprises from 0.5% to 99.9%, especially from 1% to 95%, advantageously from 1% to 50% by mass of the desired ingredient, and from 99.5% to 0.1% by mass. %, especially 99% to 5% of a solid or liquid adjuvant (including, for example, a solvent such as water), wherein the adjuvant (or adjuvant) may be a surfactant, the amount of which is based on the premixed formulation The mass is 0 to 50%, especially 0.5% to 40%.

In a preferred embodiment, independent of any other embodiment, the compound of formula (I) is in the form of a plant propagation material treatment (or protection) composition, wherein the plant propagation material protection composition additionally comprises a colorant . The plant propagation material protection composition or mixture may also include at least one polymer from a water soluble and water dispersible film forming polymer that improves the active ingredients onto the treated plant propagation material. For attachment, the polymer generally has an average molecular weight of at least 10,000 to about 100,000.

The combinations of the invention (i.e., those comprising a compound of the invention and one or more additional biologically active agents) can be administered simultaneously or sequentially.

Where the components of the combination are administered sequentially (ie, one after the other), the components are sequentially applied to each other for a reasonable period of time to achieve biological properties, such as in a few hours or a few Within days. The order of application of the ingredients in the combination, i.e., whether the compound of formula (I) should be administered first, is not critical to the practice of the invention.

In the case where the components of the combinations of the present invention are simultaneously administered, they may be administered as a composition comprising the combination, in which case (A) the compound of the formula (I) in the combinations and One or more other ingredients may be obtained from separate formulation sources and mixed together (referred to as a tank mix, ready-to-use application, broth or slurry), or (B) a compound of formula (I) And one or more other ingredients may be obtained as a single source of formulation mixture (referred to as premixed, ready to use blends, concentrates or formulated products).

In an embodiment, the compounds according to the invention are administered as a combination, independently of the other embodiments. Accordingly, the present invention also provides a composition comprising a compound according to the invention as described herein and one or more other biologically active agents, and optionally one or more conventional formulation auxiliaries; It can be in the form of a tank mix or premix composition.

As an alternative to the actual synergy in terms of biological activity, the combinations according to the invention may also have surprisingly advantageous properties which, in a broader sense, may also be described as synergistic activities. Examples of such advantageous properties that may be mentioned are: advantageous behavior during formulation and/or application (eg grinding, screening, emulsifying, dissolving or dispersing); improved storage stability; improved light stability More favorable degradability; improved toxicological and/or ecotoxicological behavior; or any other advantage familiar to those skilled in the art.

It has also been found that the compounds of the present invention can be used in other fields, such as the protection of stored goods and storage rooms, one or more of the protection of raw materials (such as wood and textiles), flooring and buildings, and can be managed in hygiene. Medium applications - especially protecting humans, livestock and producing livestock against pests. Therefore, the present invention also enables pesticidal compositions for such uses and This method is available. For use in a particular use, the composition needs to be modified, and one of ordinary skill will be able to make such compositions useful for any particular use.

In the field of hygiene, the compositions according to the invention are effective against ectoparasites such as hard palate, soft palate, cockroach, autumn cockroach, fly (bite and cockroach), parasitic larvae, cockroaches, cyanosis, Birds and dragonflies.

Examples of such parasites are: genus: blood genus, long genus, genus and genus, genus.

The genus of the genus: genus, genus, genus, genus, genus, genus Werneckiella spp., Lepikentron spp., genus, genus, and genus.

Diptera and long-horned suborders and short-horned suborders, such as Aedes, Anopheles, Culex, Amaranthus, Eucalyptus, Astragalus, Castanopsis, Corydalis, Turtle, Humpback genus, Astragalus , genus, genus, Philipomyia spp., genus, genus, Musca, genus, genus, genus, genus, genus, genus Genus, genus, genus, genus, genus, genus, genus, genus, genus, genus, genus, genus, genus, genus, genus, genus

Attention, such as genus, genus, genus, genus.

From the order of the genus Heteroptera, for example, the genus Bug, the genus Cono, the genus Red genus

Attention, such as the Oriental lynx, the American cockroach, the German cockroach and the genus Chapella.

蜱螨亚纲 (螨科) and the posterior and ventricles, such as the genus Sharpus, the genus blunt, the genus, the genus, the genus, the genus, the genus, the genus, the blood Genus, genus, genus, genus, genus, genus, genus, genus, and genus.

Axillary (pre-valve suborder) and white-eye (no valve suborder), such as the genus Aphididae, the genus Heliconia, the genus Aphis, the genus, the genus, the genus, the genus Genus, genus, whitefly, Cassia, genus, genus, genus, genus, genus, genus, genus, genus, genus, genus, genus, genus and chicken螨属.

The compositions according to the present invention are also suitable for use in protecting materials such as wood, textiles, plastics, adhesives, glues, paints, paper and cards, leather, flooring and construction from insects. The compositions according to the present invention can be used, for example, against the following pests: beetles, such as the North American geranium, the genus Green Tiger, the furniture burglary, the murder, the Ptilinuspecticornis, the Dendrobium pertinex, the fine-toothed tail蠹,Priobium carpini, brown meal, African whitefly, southern whitefly, stalked scorpion, soft-wool scorpion, flat-legged whitefly, squama, scorpion, scorpion, scorpion, black scorpion, red Abdominal scorpion scorpion, brown scorpion scorpion, scorpion scorpion, and bamboo scorpion, and also Hymenoptera, such as blue-black tree bee, big tree bee, Taigao tree bee and Urocerus augu, and termites, such as yellow Cervical termites, stalked sand termites, Indosinian structural termites, yellow-spotted termites, Sant's loose termites, European termites, Dar's o. termites, Nevada termites and Taiwanese termites, and wingless insects, Such as the fish.

Application of the compounds or compositions thereof to storage of goods, storage rooms, raw materials (such as wood and textiles), flooring and construction, and application methods for administration in sanitary management are known in the art.

The present invention also provides methods for treating, eliminating, controlling, preventing, and protecting warm-blooded animals, including humans, and fish against worms, arachnids, and infections and infections caused by internal and external parasites of arthropods. The method comprises administering or administering to the animal orally, topically or parentically, an effective amount of a compound of formula (I), which is helminthically, acaricidal, or bactericidal or ectoparasite.

The above methods are used to control or prevent infection and infection of worms, nematodes, mites and arthropods, as well as ectoparasites and warm-blooded animals (such as cattle, sheep, pigs, camels, deer, horses, poultry, fish, Infections in rabbits, goats, otters, foxes, chinchillas, dogs and cats, as well as humans, are particularly useful.

The compounds of the invention are particularly useful for controlling worms and nematodes in the context of controlling and preventing infection and infection in warm-blooded animals. Examples of worms are members of the genus Helminthidae, commonly known as trematodes or flatworms, especially the genus Trichomonas, the genus Trichomonas, the genus Diptera, the genus Bismuth, and the broad-sucking A member of the genus Ophisthorchis, the genus Ginger, the genus Ranunculus, and the genus Paragonimus. Nematodes which can be controlled by a compound of formula (I) include Haemonchus, Gastritis, Cooper nematodes, Nodular nematodes, Nematodes, Nematodes, Trichuris, Filaria , H. genus, Aphis and similar genus.

The compounds of the invention may also control endoparasite arthropod infestation, such as the sphagnum and the stomach bot. In addition, the compounds of the present invention can control, prevent or eliminate the infection of warm-blooded animals and aphids in fish and ectoparasites of arthropods, such as ticks, sucking, fly, biting, and scented flies. (muscoid flies), flies, myiasitic fly larvae, cockroaches, mosquitoes, cockroaches, cockroaches, cockroaches, nas bots, sheep ticks and cockroaches. Rodents include members of the bristles, such as bulls, canines, and sheeps. Sucking includes members of the eye, such as bovine blood, pig blood, calves and buffalo blinds. The biting fly includes members of the genus.蜱 includes burdock, genus, genus, genus, genus, and genus. The compounds of the present invention can also be used to control mites that are parasitic on warm-blooded mammals and poultry, including mites and mites.

For oral administration to warm-blooded animals, the compounds of the invention may be formulated into animal feed, animal feed premix, animal feed concentrate, pill, solution, paste, suspension, irrigant, gel, Tablets, boluses and capsules. Furthermore, the combinations of the invention can be They are given to them in the drinking water of animals. For oral administration, the selected dosage form should provide the animal with a compound of the invention from about 0.01 mg/kg to about 100 g/kg of animal body weight per day.

Alternatively, the compounds of the invention may be administered parenterally to the animal, for example, by rumen, intramuscular, intravenous or subcutaneous injection. The compounds of the invention may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compounds of the invention may be formulated as implants for subcutaneous administration. Furthermore, the compounds of the invention may be administered to the animal transdermally. For parenteral administration, the selected dosage form should provide the animal with a compound of the invention from about 0.01 mg/kg to about 100 mg/kg of animal body weight per day.

The compounds of the invention may also be topically applied to the animal in the form of infusions, dusts, powders, collars, medallions, sprays, and pour-on formulations. For topical application, the infusions and sprays will generally comprise from about 0.5 ppm to 5,000 ppm, and preferably from about 1 ppm to 3,000 ppm of the compound of the invention. In addition, the compounds of the invention may be formulated as ear tags for use in animals, particularly tetrapods such as cattle and sheep.

The compounds of the invention may also be used in combination or in combination with one or more other parasiticidal compounds (and thus broaden the range of activity), including but not limited to anthelmintic agents such as benzimidazole, piperidine , levamisole, pyrantel, praziquantel and the like; endoparasites such as avermectin, milbemycin and the like; ectoparasites such as arylpyrrole, organophosphate, amine Formate, gamma-butyric acid inhibitors (including fipronil, pyrethroid, spinosyn, imidacloprid) and the like; insect growth regulators such as pyriproxyfen, ciprofloxacin and the like; Chitin synthase inhibitors such as benzalazine (including flubendiamide).

The parasiticidal composition of the present invention comprises a parasiticidally effective amount of a compound of the present invention or a combination thereof in admixture with one or more physiologically acceptable inert solid or liquid carriers, such carriers It is known in veterinary pharmaceutical practice for oral, transdermal and topical administration. Such compositions may include additional additives such as stabilizers, defoamers, viscosity modifiers, binders, and tackifiers, while commercial products will preferably be formulated as concentrates that the end user will typically A diluted formulation was used.

The compositions according to the invention may also be used in the preparation of compositions for the therapeutic or prophylactic treatment of fungal diseases of humans and animals such as, for example, mycosis, skin diseases, rickets and candidiasis Or a disease caused by Aspergillus (eg, Aspergillus fumigatus).

In an embodiment, the compound of formula (I) is an anthelmintic compound, independent of any other embodiment.

In an embodiment, the compound having formula (I) is a pesticidal compound, preferably a nematicidal compound, independently of any other embodiment.

In each of the aspects and embodiments of the present invention, "consisting essentially of" and variations thereof "including" and variations thereof are preferred embodiments, and "consisting of" and variations thereof are "mainly A preferred embodiment of "composed of" and variations thereof.

The disclosure in this application makes the combinations of the embodiments disclosed herein available individually and in all.

The following examples are presented to demonstrate the invention. They do not limit the invention. The temperature is given in degrees Celsius and the solvent mixing ratio is given in parts by volume.

Example

Preparation Example 1: 3-methyl-pyridine-2-carboxylic acid (1-o-tolyl-cyclopropylmethyl)-decylamine (Compound A.9)

Step 1: C-(1-o-tolyl-cyclopropyl)-methylamine (Compound Q.1)

4.56 g of 1-o-tolyl-cyclopropanenitrile was dissolved in 150 ml of methanol, and 40 ml of aqueous ammonia (solution of 7 N in methanol) was added, followed by addition of 4.5 g of Raney Nickel. . The reactor was sealed and the reaction mixture was stirred at ambient temperature for 1 day under 1 bar of hydrogen. The reaction mixture was then filtered through celite and the filtrate was concentrated. The residue was purified by silica gel chromatography (ethyl acetate / methanol / triethylamine (90: 5: 5) as eluent). Thus, 4.01 g of C-(1-o-methylphenyl-cyclopropyl)-methylamine as an oil was obtained. ¹ H-NMR (CDCl ₃ ): 7.25 ppm (m, 1H), 7.13 ppm (m, 3H), 2.70 ppm (s, 2H), 2.41 ppm (s, 3H), 1.40 ppm (s, 2H, Width) , 0.80 ppm (m, 4H).

Step 2: 3-Methyl-pyridine-2-carboxylic acid (1-o-tolyl-cyclopropylmethyl)-decylamine (Compound A.9)

150 mg of C-(1-o-methylphenyl-cyclopropyl)-methylamine (step 1) was dissolved in 5 ml of dichloromethane and cooled to 0 °C. Then 188 mg of triethylamine was added followed by a dropwise addition of a solution of 145 mg of 3-methyl-pyridine-2-carbonium chloride in 1 ml of dichloromethane. The reaction mixture was stirred at ambient temperature for 3 days. Then, 6 ml of water was added, the obtained phases were separated, and the organic phase was washed with 2N aqueous sodium hydroxide, then 1N aqueous hydrochloric acid and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by EtOAc (EtOAc/EtOAc (EtOAc:EtOAc) Thus, 51 mg of 3-methyl-pyridine-2-carboxylic acid (1-o-tolyl-cyclopropylmethyl)-decylamine as an oil was obtained. ¹ H-NMR (CDCl ₃ ): 8.83 ppm (m, 1H), 8.15 ppm (s, 1H, broad), 7.55 ppm (m, 1H), 7.30 ppm (m, 1H), 7.27 ppm (m, 1H) , 7.12 ppm (m, 3H), 3.55 (d, 2H), 2.70 ppm (s, 3H), 2.50 ppm (s, 3H), 1.02 ppm (m, 2H), 0.82 ppm (m, 2H).

Preparation Example 2: N-[[1-(4-Cyano-2,6-difluoro-phenyl)cyclopropyl]methyl]-2-(trifluoromethyl)benzamide (Compound A .57)

N-[[1-(4-Bromo-2,6-difluoro-phenyl)cyclopropyl]methyl]-2-(trifluoromethyl)benzamide (100 mg) under an inert atmosphere And Zn(CN)2 (16.2 mg) was dissolved in deoxygenated DMF. Pd(PPh3)4 (13.5 mg) was added and the vial was sealed under an inert atmosphere in a preheated 80 ° C oil bath and stirred for 2.5 hrs. TLC showed only traces of product. Pd(PPh3)4 (13.5 mg) and Zn(CN)2 (16.2 mg) were added, and the reaction mixture was stirred at 80 ° C overnight. TLC showed only traces of product, Pd(PPh3)4 (27 mg) and Zn(CN)2 (32.4 mg) were added, and the RM was stirred at 100 ° C to form a yellow solution with a white precipitate. TLC shows almost complete conversion. The reaction mixture was cooled to rt and diluted with EtOAc EtOAc (EtOAc)EtOAc. Preparative TLC: Hexane: EtOAc 4:1

71.7 mg of the product as a yellow solid are obtained, m.p. 100 °C - 102 °C.

¹ H-NMR (CDCl ₃ ): 8.72 (d, 1H); 8.26 (d, 1H); 7.89 (br s, 1H); 7.58 (dd, 1H); 7.15 (m, 2H); 3.63 (d, 2H) ); 1.16 (t, 2H); 0.98 (t, 2H).

Preparation Example 3: N-[[1-(4-cyclopropyl-2,6-difluoro-phenyl)cyclopropyl]methyl]-2-(trifluoromethyl)benzamide (Compound) A.58)

N-[[1-(4-Bromo-2,6-difluoro-phenyl)cyclopropyl]methyl]-2 in toluene (1.5 ml) and water (0.04 ml) -(Trifluoromethyl)benzamide (100 mg), cyclopropylboronic acid (66 mg), P(Cy)3 (13 mg), and K3PO4 (349 mg) with Pd(OAc)2 (5.3 mg) ). The reaction mixture was heated to 100 ° C for 22 hours. EtOAc and water were added and the phases were separated. The organic layer was washed with brine, dried over Na.sub.2SO.sub.4, and concentrated to give 210 mg of light brown oil. Prepared TLC (hexanes: EtOAc 9:1, eluted 7 times): ield: 165.4 mg of product as a yellow oil, ¹ H-NMR (CDCl ₃ ): 8.73 (d, 1H); 8.12 (d, 1H) 7.89(br s,1H);7.53(dd,1H);6.53(m,2H);3.55(d,2H);1.82(m,1H);1.08-0.86(m,6H);0.63(m) , 2H).

Preparation Example 4: N-[[1-(2,4,6-trichlorophenyl)cyclopropyl]methyl]-3-(trifluoromethyl)pyridine-2-carboxamide (Compound A29)

Step 1:1, 3,5-trichloro-2-(chloromethyl)benzene

To a stirred solution of (2,4,6-trichlorophenyl)methanol (2 g, 9.4574 mmol) in chloroform (20 mL) at 0 ° C over a period of 10 min. Slowly add sulphide chloride (1.25 mL, 17.023 mmol) followed by a catalytic amount of DMF (35 mg, 0.4733) Mm). The reaction mixture was allowed to stir at RT for 2 h.

The reaction mixture was quenched with 10 mL of water; and aqueous layer was extracted with dichloromethane (3). The combined organic layers were washed with 5% aq. Na2CO3 (2*10 mL) then NaCI (10 mL) and dried over Na2SO4. The solvent was evaporated under reduced pressure to give a yellow oil (1.78 g). The oil was diluted with EtOAc and EtOAc (EtOAc)EtOAc.

¹ H-NMR (CDCl ₃ ): 7.4 (s, 2H); 4.8 (s, 2H).

Step 2: 2-(2,4,6-Trichlorophenyl)acetonitrile

Add NaCN in H2O (1.7 mL) to a stirred solution of 1,3,5-trichloro-2-(chloromethyl)benzene (1.7 g, 7.39 mmol) in EtOH (5.7 mL). (0.411 g, 8.13 mmol). The reaction mixture was refluxed for 4 h to complete the reaction.

EtOH was evaporated and the white solid was diluted in water (6 mL). The aqueous layer was extracted with EtOAc (3 times). The combined organic layers were washed with brine (10 mL) and dried over Na.sub.2SO. The solvent was evaporated under reduced pressure to give a white solid (l.

The crude product was purified by flash chromatography (EtOAc/EtOAc (EtOAc/EtOAc)

¹ H-NMR (CDCl ₃ ): 7.45 (s, 2H); 3.95 (s, 2H).

Step 3: 1-(2,4,6-Trichlorophenyl)cyclopropanenitrile

2-(2,4,6-trichlorobenzene) was added dropwise to a solution of 60% NaH (0.387 g, 9.67 mmol) in dry THF (1.5 mL) in oil under argon at 0 °C. A solution of acetonitrile (0.748 g, 3.22 mmol) in THF (1.5 mL). The yellow mixture was stirred until the end of gas formation. Then, 1,2-dibromoethane (2.45 g, 12.9 mmol) was added dropwise at 0 °C. The reaction mixture was stirred at 0 °C for 30 min and allowed to stand at RT for 2 hr.

The reaction mixture was quenched with aqueous NH4CI (12 mL). Add EtOAc. Separate the phases. The aqueous phase was extracted again with EtOAc. The combined organic phases with Na ₂ SO ₄ dried, filtered, and the organic phase was evaporated to give a pink solid (1.42 g of), the solid by flash chromatography (solvent: cyclohexane / EtOAc 4/1 Purification was carried out to give a white solid (0.704 g).

¹ H-NMR (CDCl ₃ ): 7.4 (s, 2H); 1.95 (m, 2H), 1.45 (m, 2H).

Step 4: [1-(2,4,6-Trichlorophenyl)cyclopropyl]methylamine

To a solution of 1-(2,4,6-trichlorophenyl)cyclopropanenitrile (0.702 g, 2.85 mmol) in Et.sub.2O (6 mL) was carefully added to Et2O (4.27 mL, 4.27). LiAlH4 (1 M) in mmol) (exothermic, keeping T° between 5 °C and 10 °C). The suspension was then stirred at 0 ° C for 1 hr. The reaction mixture was then diluted, 6 mL of Et2O was added, and then carefully washed with 3 ml of water (exothermic, vigorous, gas) at 0 ° C, then quenched with 6 mL of 4 M aqueous NaOH and then 9 mL of water. . The reaction mixture was stirred at RT for 10 min then Na2SO4 was added and the mixture was stirred for 5 min. All salts were filtered through diatomaceous earth. The organic phase was washed with brine. The organic layer was dried with Na ₂ SO _4, the organic phase was filtered and evaporated to give a yellow oil (524 mg).

¹ H-NMR (CDCl ₃ ): 7.35 (s, 2H); 2.85 (s, 2H), 1.6 (bs, 2H), 1.0 (m, 2H), 0.95 (m, 2H).

Step 5: N-[[1-(2,4,6-Trichlorophenyl)cyclopropyl]methyl]-3-(trifluoromethyl)pyridine-2-carboxamide (Compound A29)

To argon (E.g. 0.129 mL, 0.915 mmol), then the mixture was cooled at 0 °C. Then EDCI.HCl (0.175 g, 0.915 mmol), HOBT.H2O (0.125 g, 0.915 mmol), 3-(trifluoromethyl)pyridine-2-carboxylic acid (0.0874 g, 0.458 mmol) were added and the reaction was The mixture was stirred at RT. Water was added, the aqueous solution was extracted with methylene chloride (3×), and the combined organic layer was washed with NaCI, dried over Na2SO4, filtered and evaporated under reduced pressure to give a yellow oil (198 mg). The crude product was purified by EtOAc EtOAc (EtOAc:EtOAc)

¹ H-NMR (CDCl ₃ ): 8.7 (d, 1H); 8.15 (d, 1H), 8.0 (bs, 1H), 7.55 (m, 1H), 7.3 (s, 2H), 3.67 (d, 2H) , 1.25 (m, 2H), 1.05 (m, 2H).

Preparation Example 5: 3-Chloro-N-[[1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropyl]methyl]pyridine-2-carboxamide (Compound A37)

Step 1: 1-[2-Fluoro-4-(trifluoromethyl)phenyl]cyclopropanenitrile

2-Fluoro-4-(trifluoromethyl)phenylacetonitrile (3 g, 14, 47 mmol) was dissolved in THF (30 mL). Sodium hydride (1.7366 g, 43.42 mmol) was added portionwise at 0 °C. The reaction mixture was stirred until no gas evolution was detected. The reaction mixture was then a red suspension. 1-Bromo-2-chloro-ethane (4.80 mL, 57,89 mmol) was added dropwise at 0 °C. The reaction mixture was stirred at 0 ° C for 30 min and then at 50 ° C for 2 h. . Cool it down to rt. The suspension was filtered through Hyflo. The filtrate was evaporated. The residue was 3.7 g dark red liquid/oil. The crude product was purified by flash chromatography (EtOAc:EtOAc:EtOAc

¹ H-NMR (CDCl ₃ ): 7.5 (t, 1H), 7.45-7.35 (m, 2H), 1.75 (m, 2H), 1.45 (m, 2H).

Step 2: [1-[2-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl]methylamine

Carefully added to a solution of 1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropanenitrile (1.926 g, 8.404 mmol) in Et2O (20 mL, 8.40 mmol) at 0 °C LiAlH4 (1 M) in Et2O (6.723 mL, 6.723 mmol) (exothermic, keeping T° between 5 °C and 10 °C). The colorless solution was converted to an orange suspension which was stirred at 0 ° C for 1 h. Since some of the starting material remained, 1.6 mL of LiAlH4 (1 M in Et2O) was added and the reaction mixture was stirred for an additional hour. The reaction mixture was then diluted, 20 mL of Et2O was added, and then quenched with 6 ml of water (exothermic, vigorous, gas) at 0 ° C, then 5 mL of 2 M aqueous NaOH and then 6 mL of water. Off. The reaction mixture was stirred at RT for 10 min then Na2SO4 was added and the mixture was stirred for a further 5 min. All salts were filtered through diatomaceous earth. The filtrate was washed with brine. The organic layer was dried Na ₂ SO _4, filtered and evaporated to give a yellow oil of the desired product (1.66 g).

¹ H-NMR (CDCl ₃ ): 7.44 (t, 1H), 7, 37 (d, 1H), 7, 30 (d, 1H), 2, 80 (s, 2H), 1, 15 (bs, 2H) ), 0.84 (m, 4H).

Step 3: 3-Chloro-N-[[1-[2-fluoro-4-(trifluoromethyl)phenyl]cyclopropyl]methyl]pyridine-2-carboxamide (Compound A37)

To [1-[2-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl]methylamine (0.500 mL, 0.510 mmol) in dry dichloromethane (2.0 mL, 0.510 mmol) Et3N (0.144 mL, 1.02 mmol) was added to the solution and the mixture was cooled at 0 °C. Add EDCI.HCl (0.196 g, 1.02 mmol), HOBT.H2O (0.139 g, 1.02 mmol), 3-chloropyridine-2-carboxylic acid (0.0803 g, 0.510 mmol), and the reaction mixture was stirred at RT overnight. . Water was added, the aqueous solution was extracted with dichloromethane (3 times), the combined organic layer was washed with NaCI, dried over Na2SO4, filtered and evaporated under reduced pressure to give oil (0.316 mg) Purification was carried out by flash chromatography (cyclohexane to cyclohexane / AcOEt: 4/1). The desired compound (143.0 mg) was obtained as a colourless oil.

¹ H-NMR (CDCl ₃ ): 8.43 (d, 1H), 7.88 (bs, 1H), 7.80 (d, 1H), 7.46 (t, 1H), 7.40-7.30 (m, 3H), 3.63 (d, 2H), 1.10 (m, 2H), 0.91 (m, 2H).

The compounds in Tables A & Q were prepared according to the methods described above.

LC-MS method: ZDQ11

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

Instrument parameters: ionization method: electric sprinkler

Polarity: positive and negative ions

Capillary: 3.00 kV

Cone disk: 30.00 V

Extractor: 2.00 V

Source temperature: 100 ° C, Desolvation gas temperature: 250 ° C

Cone blowback airflow: 50 L/Hr

Desolvent gas flow: 400 L/Hr

Quality 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 x 3 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

LC-MS method: ZDQ12

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 gas 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 μm, 30 x 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

LC-MS method: ZCQ11

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: 30.00 V

Extractor: 2.00 V

Source temperature: 100 ° C, desolvation gas temperature: 250 ° C

Cone blowback airflow: 50 L/Hr

Desolvent gas flow: 400 L/Hr

Quality range: 100 to 900 Da

HP 1100 HPLC from Agilent: solvent degasser, quaternary pump, heated column chamber and diode array detector.

Column: Phenomene x Gemini C18, 3 mm, 30 x 3 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

LC-MS method: ZMD11

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

Instrument parameters: ionization method: electric sprinkler

Polarity: positive or negative ion

Capillary: 3.80 kV

Cone disk: 30.00 V

Extractor: 3.00 V

Source temperature: 150 ° C, Desolvation gas temperature: 350 ° C

Cone blowback airflow: off

Desolvent gas flow: 600 L/Hr

Quality range: 100 to 900 Da

HP 1100 HPLC from Agilent: solvent degasser, binary pump, heated column chamber and diode array detector.

Column: Phenomene x Gemini C18, 3 mm, 30 x 3 mm, Temperature: 60 ° C

DAD wavelength range (nm): 200 to 500

Solvent gradient: A = H ₂ O + 5% MeOH + 0.05% HCOOH

B = acetonitrile + 0.05% HCOOH

LC-MS method: 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 gas 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 μm, 30 x 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 example Root-knot nematode (root knot nematode) contact activity, preventive. Pouch test.

Place a filter paper (9 cm x 4.5 cm) with a small pocket in a plastic pouch (12 cm x 6 cm). Seeds of a cucumber variety, Toshka, were placed in the center of the filter paper pockets of all the bags required for testing. The cucumber seeds in the bags were treated with 200 ppm of the test solution by directly drawing the solution onto the cucumber seeds in the filter paper pocket in the pouch. Prior to application, a compound solution of twice the desired concentration was prepared and a 3000 egg/0.5 ml egg suspension was prepared with FORL nutrient solution. After all treatments were applied, 3000 eggs (in 0.5 ml of FORL nutrient solution) were pipetted into the bags. The pouches were incubated in a moisturizing chamber for twelve days and periodically watered to maintain good filter paper moisture necessary for cucumber root system growth. After this period, the filter paper containing the germinated cucumber seedlings was removed from the plastic bag to assess the number of insects caused by the root knot nematode on each root system.

The following compounds showed more than 75% reduction in worms compared to untreated controls: A.1, A.2, A.3, A.5, A.6, A.7, A.9, A .11, A.12, A.15, A.18, A.65, A.66, A.67, A.68, A.69, A.70, A.73, A.77, A.84 , A.85, A.94, A.101.

Root-knot nematode (root knot nematode) contact activity, preventive, and drug-filling test.

The seeds of the cucumber variety Toshka are directly sown in pots filled with sandy substrates. Six days later, the pots were each treated with 5 ml of a WP10 suspension with 20 ppm test compound. Thereafter, the pots were inoculated with eggs of 3000 M. incognita. The test was harvested 14 days after the test application and inoculation. The root worms were evaluated according to the Zeck`s worm index (Zeck, 1971).

The following compounds showed more than 75% reduction in worms compared to untreated controls: A.1, A.2, A.3, A.6, A.7, A.12, A.14, A .15, A.17, A.19, A.21, A.22, A.23, A.24, A.25, A.27, A.28, A.31, A.32, A.35 , A.36, A.37, A.38, A.49, A.50, A.56, A.57, A.58, A61 A.62, A.65, A.66, A.67, A.72, A.73, A.76, A.77, A.78, A.81, A.84, A.85, A.94, A.95, A.96, A.97, A. 100, A.101.

Claims (39)

a compound of formula (I) wherein Wherein R 1 is hydrogen, methyl or halogen; R 2 is hydrogen, methyl or halogen; R 3 is hydrogen, methyl or halogen; R 4 is hydrogen, methyl or halogen; R 5 is substituted or unsubstituted phenyl; R6 is hydrogen or C1-C4-alkyl; R7 is hydrogen, cyano, hydroxy, formyl, C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4- Alkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-cyanoalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, benzyl, C3-C6 - cycloalkylcarbonyl or C3-C6-cycloalkoxycarbonyl; A1 is N, CH or CX; A2 is N, CH or CX; A3 is N, CH or CX; A4 is N, CH or CX; N, CH or CX; the condition is that wherein A1 & A5 are each N, then A2 to A4 are independently selected from CH, CX and N; or wherein A2 is CX, then A1, A3 to A5 are independently selected from CH, N or CX; or wherein A1 is CX and A5 is N, then A2 to A4 are independently selected from CX and CH; or wherein A1 is CX and A5 is CH, then one of A2 to A4 is CX and each of the remaining CH; or wherein A1 is CX and A4 is N, then A2, A3 and A5 are independently selected from CX and CH; or A1 is other than C-halogen and A2 is N, then A3, A4 and A5 are independently selected from CX and CH; X-based halogen, OH, cyano, C1-C4-alkyl, C1-C4-haloalkyl a C1-C4-alkoxy group or a C1-C4-haloalkoxy group; the conditions are at most three N groups of A1 to A5; together with acceptable salts, enantiomers, diastereomers thereof , tautomers and N-oxides. The compound of claim 1, wherein each of R1 to R4 is hydrogen; R5 is substituted or unsubstituted phenyl; R6 is hydrogen or C1-C4-alkyl; R7 is hydrogen, C1 -C4-alkylcarbonyl or C1-C4-alkoxycarbonyl; and each of A1 & A5 is N, then A2 to A4 are independently selected from CH, CX and N; or A2 is CX, then A1, A3 are A5 is independently selected from CH, N or CX; or A1 is CX and A5 is N, then A2 to A4 are independently selected from CX and CH; or A1 is CX and A5 is CH, then one of A2 to A4 CX and the remainder of each CH; or A1 is CX and A4 is N, then A2, A3 and A5 are independently selected from CX and CH; wherein X is independently of each other halogen, C1-C4-alkyl or C1-C4- Haloalkyl. A compound of formula (I) as defined in claim 1 wherein R1 to R4 are each hydrogen; R5 is substituted or unsubstituted phenyl; R6 is hydrogen or C1-C4-alkyl ; R7 is hydrogen, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl; A1 is in addition to C-halogen, A2 is N and A3, A4 and A5 are independently selected from CX and CH; wherein X is each other Independently halogen, C1-C4-alkyl or C1-C4-haloalkyl, along with acceptable salts, enantiomers, diastereomers, tautomers and N-oxides thereof. The compound of claim 3, wherein A1 is C-C1-C4-haloalkyl, A2 is N, and A3, A4 and A5 are independently selected from CX and CH; wherein X is independently of each other halogen , C1-C4-alkyl or C1-C4-haloalkyl; preferably, A1 is C-CF3, A2 is N and each of A3, A4 and A5 is CH. The compound of any one of claims 1 to 4 wherein X is independently of each other a halogen or a C1-C4-haloalkyl group. A compound of formula (I) as defined in claim 1 wherein R1 to R4 are each hydrogen; R5 is selected from cyano substituted phenyl (which may optionally be halogen or trifluoro) Methyl further substituted), 2-fluoro-4-trifluoromethylphenyl, 2,6-difluoro-4-chloro-phenyl, 2,4-difluorophenyl, 2,4,6-trifluoro Phenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-4-bromophenyl, 2-chloro-4-fluorophenyl, 2-chloro-4-trifluoromethylphenyl, 3,4, 5-trifluorophenyl, 2,4-dichloro-6-fluorophenyl, and 2,4-dibromophenyl; R6 hydrogen or C1-C4-alkyl; R7 hydrogen, C1-C4-alkane Alkylcarbonyl or C1-C4-alkoxycarbonyl; and A1 is CX, and A2 to A5 are each CH; or A1 and A5 are each CX, and A2 to A4 are each CH; or A1 is CX, A2 And A5 is each N, and A3 and A4 are each CH; or A1 is CX, A2 is N, and A3 to A5 are each CH, wherein X is independently selected from halogen, C-C4-alkyl or C1 -C4-haloalkyl, together with its acceptable salts, enantiomers, diastereomers, tautomers and N-oxides. a compound of formula (I) as defined in claim 1 of the scope of claim, wherein R1 To R4 each is hydrogen; R5 is 2,4-chlorophenyl; R6 is hydrogen or C1-C4-alkyl; R7 is hydrogen, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl; A1 is C-Cl, and A2 to A5 are each CH; or A1 is CF, A2 and A5 are each N, and A3 and A4 are each CH; or A1 and A5 are each C-Cl or C- CF3 and A2 to A4 are each CH; or A1 is CF or C-CF3, A2 is N, and A3 to A5 are each CH, together with acceptable salts, enantiomers, diastereomers thereof Bulks, tautomers, and N-oxides. The compound of claim 6, wherein X is independently of the configuration of A1 to A5 and is independent of X in the A1 to A5 configuration, and is selected from the group consisting of chlorine, fluorine, trifluoromethyl, and difluoromethyl; A1 is C-CF3, and A2 to A5 are each CH; or A1 and A5 are each CF, and A2 to A4 are each CH; or A1 is C-CF3 or Cl, A2 and A5 are each N, and A3 and A4 are each CH; or A1 is C-CF3, A2 is N, and A3 to A5 are each CH. The compound of claim 1, or the compound of claim 2, wherein A1 is N or CX, and the groups A2, A3, and A4 and A5 are selected from each of (I) A2, A3, and A4. CH, and A5 is N; (II) A2 is CX, and A3, A4, and A5 are each CH; (III) A3 is CX, and A2, A4, and A5 are each CH; and (IV) A4 is CX And A2, A3, and A5 are each CH. The compound of claim 1 or claim 2, wherein each of A1 & A5 is N, then A2 to A4 are independently selected from CH, CX and N; or wherein A2 is CX, then A1 A3 to A5 are independently selected from CH, N or CX; or wherein A1 is CX and A5 is N, then A2 to A4 are independently selected from CX and CH; preferably A1 & A5 are each N, then A2 Each line to A4 is CH; or A2 is CX, A1 CX, and A3 to A5 are each CH; or where A1 is CX and A5 is N, then A2 to A4 are each CH. The compound of any one of claims 1 to 5, 9 and 10, wherein R5 is a substituted phenyl group independently selected from the group consisting of halogen, cyano, C1-C4-alkyl, C1 a substituent of -C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, which is unsubstituted or one or more Substituted for the substituent Rx wherein Rx is independently of each other selected from the group consisting of halogen, C1-C4-alkyl, and C1-C4-haloalkyl. The compound of claim 11, wherein the substituent on the phenyl group at R5 is independently selected from the group consisting of halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4 An alkoxy group, a C1-C4-haloalkoxy group, and a C3-C6-cycloalkyl group. The compound of any one of claims 1 to 5 and 9 to 12, wherein R5 is a substituted phenyl group having one to three substituents, preferably two or three substituents, More preferred are two substituents. The compound of claim 1 to 5, wherein the phenyl group at R5 is substituted with an optionally substituted phenyl group or an optionally substituted pyrazole. The compound of claim 12, wherein the substituents are independently selected from the group consisting of chlorine, methyl, fluoro, trifluoromethyl, cyclopropyl, and cyano. The compound of any one of claims 1 to 5 and 9 to 15, wherein A1 is N or C-X, A2, A3 and A4 are C-H, and A5 is N. The compound of any one of claims 1 to 5 and 9 to 15, wherein A1 is N or C-X, A2 is C-X, and each of A3, A4 and A5 is C-H. A compound according to any one of claims 1 to 5 and 9 to 15, which Medium A1 is N or C-X, A3 is C-X, and A2, A4 and A5 are C-H. The compound of any one of claims 1 to 5 and 9 to 15, wherein A1 is N or C-X, A4 is C-X, and each of A2, A3 and A5 is C-H. The compound of any one of claims 1 to 5 and 9 to 15, wherein A1 is C-C1-C4-haloalkyl, A2 is N, and each of A3, A4 and A5 is C-H. The compound of any one of claims 1 to 5 and 9 to 15, wherein A1 is C-X, A2, A3 and A4 are C-H, and A5 is N. The compound of any one of claims 1 to 21 wherein R6 is hydrogen or C1-C2-alkyl, preferably hydrogen. The compound of any one of claims 1 to 22, wherein R7 is hydrogen. The compound of claim 16, wherein A1 is CX, A2, A3 and A4 are C-H, and A5 is N. The compound of claim 16, wherein A1 is N, A2, A3, and A4 is C-H, and A5 is N. The compound of any one of claims 1 to 5 and 9 to 24, wherein X in CX of A1 to A5 is independently selected from the group consisting of halogen, C1-C2-alkyl and C1-C2-halogen. Alkyl; preferably, independently selected from the group consisting of chloro, fluoro, methyl, and trifluoromethyl. A compound of formula (I) as defined in claim 1 wherein R1 to R4, R6 and R7 are each hydrogen; R5 is a mono to trisubstituted phenyl group, wherein the substituents are independently selected From halogen, C1-C4-alkyl, halogen C-C4-alkyl, cyano and C3-C6-cycloalkyl; A1 to A5 are as in any of claims 16 to 21, 24 and 25 And X are independently of each other halo, C1-C2-alkyl or C1-C2-haloalkyl, together with acceptable salts thereof, Enantiomers, diastereomers, tautomers, and N-oxides. A composition comprising a compound as defined in any one of claims 1 to 27 and an agronomic carrier and optionally one or more conventional formulation auxiliaries. The composition of claim 28, further comprising one or more other biologically active compounds. A method of controlling damage and/or yield loss caused by pests and/or fungi, the method comprising administering an effective amount of formula (I) as defined in any one of claims 1 to 27 of the patent application. The compound or the composition as defined in claim 28 or 29 is applied to a pest, a pest site, or a plant susceptible to attack by pests and/or fungi or to a plant propagation material. A method for protecting plant propagation material from damage and/or yield loss caused by pests and/or fungi, the method comprising determining an effective amount as defined in any one of claims 1 to 27 The compound of formula (I) or the composition as defined in claim 29 or 30 is applied to the propagation material or to the location where the propagation material is planted. The method of claim 30, wherein the pest is selected from the group consisting of a nematode. A treated plant propagation material, wherein the plant propagation material is attached to an effective amount of a compound of formula (I) as defined in any one of claims 1 to 27. A pharmaceutical composition for controlling worms, arachnids or arthropod internal or external parasites, the composition comprising as defined in any one of claims 1 to 27 A compound of formula (I), a physiologically acceptable carrier, and optionally one or more conventional formulation auxiliaries. A pharmaceutical composition for preventing infection of a disease transmitted by worms, arachnids or arthropods, or a parasite, the composition comprising as defined in any one of claims 1 to 27. A compound, a physiologically acceptable carrier, and optionally one or more conventional formulation auxiliaries. The composition of claim 25, further comprising one or more other biologically active compounds. A method for treating, controlling, preventing or protecting a warm-blooded animal or a fish against infection or infection by worms, arachnids or arthropod internal or external parasites, the method comprising administering an effective amount of parasiticidal A compound having the formula (I) as defined in any one of claims 1 to 27, or a composition as defined in any one of claims 34 to 36, which is orally, partially or not Administered or administered to the animal or fish. A method for the preparation of a composition for treating, controlling, preventing or protecting a warm-blooded animal or a fish against worms, arachnids or arthropods or infestations or infections of an arthropod, the composition comprising A compound of formula (I) as defined in any one of claims 1 to 27. A process for the preparation of a compound of formula (I), which comprises reacting a compound of formula (II) with a compound of formula (VII) Wherein R1 to R7, A1, A2, A3, A4 and A5 are as defined in any one of claims 1 to 27, and Xb is selected from a halide and a leaving group of a hydroxyl group.