TWI804514B - Pyrimidinium compounds and their mixtures for combating animal pests - Google Patents

Abstract

The present invention relates to pyrimidinium compounds of formula (I), to the stereoisomers, salts, tautomers and N-oxides thereof, their mixtures and to compositions comprising such compounds or mixtures. The invention also relates to methods and uses of these pyrimidinium compounds and of compositions thereof, for combating and controlling animal pests. Furthermore, the invention relates also to pesticidal methods of applying such substituted pyrimidinium compounds. The pyrimidinium compounds of the present invention are defined by the following general formula (I):

wherein R¹ , R² and Het are defined as in the description.

Description

Pyrimidinium compounds and mixtures thereof for use against animal pests

The present invention relates to insecticidal pyrimidinium compounds and/or compositions comprising such compounds for use against invertebrate pests. The invention further relates to mixtures of these compounds with other active ingredients having a synergistically potentiating effect. The present invention also relates to methods of killing pests, and to the uses and applications of the pyrimidinium compounds described in the present invention and their stereoisomers, salts, tautomers and N-oxides, mixtures thereof and compositions containing them.

Invertebrate pests, especially insects, arthropods and nematodes, can damage growing and harvested crops and attack wooden residential and commercial structures, causing huge economic losses to food supplies and property. Although a large number of pesticidal agents are known, there is a continuing need for new agents for combating invertebrate pests such as insects, arachnids and nematodes due to the ability of target pests to develop resistance to such agents. It was therefore an object of the present invention to provide compounds which have good pesticidal activity and which exhibit a broad spectrum of activity against a large number of different invertebrate pests, especially against difficult-to-control insects, arachnids and nematodes.

It has been found that these objects can be achieved by pyrimidinium compounds of general formula (I) as defined below, including their stereoisomers, their salts, especially their agriculturally or veterinarily acceptable salts, their mutual isomers and their N-oxides.

其中 R¹ 為C₁ -C₄ 烷基、C₃ -C₆ 環烷基、C₂ -C₄ 烯基或苯甲基，該等基團可經鹵素或C₁ -C₄ 烷基部分或完全取代； R² 為五員或六員碳環或雜環，該環可未經取代、經R^2a 部分或完全取代； Het係選自D-1、D-2及D-3：

其中 R^a 為鹵素、C₁ -C₄ 鹵烷基、C₁ -C₄ 烷氧基或C₁ -C₄ 烷硫基或苯基， n為0、1或2，及 #表示式(I)中之鍵； R^2a 為鹵素、C₁ -C₆ 鹵烷基、C₁ -C₆ 鹵烷氧基、OR^c 、C(=O)OR^c 、C(=O)NR^b R^c 、苯基或吡啶基，其可經鹵素、C₁ -C₆ 鹵烷基或C₁ -C₆ 鹵烷氧基取代； R^b 各自獨立地為氫、C₁ -C₆ 烷基、C₁ -C₆ 鹵烷基、C₁ -C₆ 烷氧基、C₁ -C₆ 鹵烷氧基； R^c 各自獨立地為氫、C₁ -C₄ 烷基、C₁ -C₄ 鹵烷基、C₁ -C₆ 環烷基； 其中兩個偕鍵結之基團R^b R^b 、R^c R^b 或R^c R^c 與其所鍵結原子一起可形成3員、4員、5員、6員或7員飽和、部分不飽和或芳族碳環或雜環； 或其立體異構體、互變異構體、鹽或N-氧化物。The present invention relates to pyrimidinium compounds of formula (I)

wherein R ¹ is C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₄ alkenyl or benzyl, these groups can be modified by halogen or C ₁ -C ₄ alkyl moiety or Fully substituted; R ² is a five-membered or six-membered carbocyclic or heterocyclic ring, which can be unsubstituted, partially or completely substituted by R ^2a ; Het is selected from D-1, D-2 and D-3:

Wherein R ^a is halogen, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio or phenyl, n is 0, 1 or 2, and # represents the formula (I ) in the bond; R ^2a is halogen, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ haloalkoxy, OR ^c , C(=O)OR ^c , C(=O)NR ^b R ^c , Phenyl or pyridyl, which may be substituted by halogen, C ₁ -C ₆ haloalkyl or C ₁ -C ₆ haloalkoxy; R ^b is each independently hydrogen, C ₁ -C ₆ alkyl, C ₁ - C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ haloalkoxy; R ^c each independently hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₆ cycloalkyl group; where the two gem-bonded groups R ^b R ^b , R ^c R ^b or R ^c R ^c can form 3-membered, 4-membered, 5-membered, 6-membered groups together with the atoms to which they are bonded or 7-membered saturated, partially unsaturated or aromatic carbocyclic or heterocyclic rings; or stereoisomers, tautomers, salts or N-oxides thereof.

WO2014/167084 describes certain substituted pyrimidinium compounds for use against invertebrate pests.

The invention also relates to non-racemic compounds of formula (I), wherein the variables Het, ^R and ^R are as defined for compounds of formula (I);

The present invention also relates to compounds of formula (I) having enantiomeric excess formula (IR), wherein the variables Het, ^R and ^R are as defined for compounds of formula (I);

Pyrimidinium compounds of formula (I), non-racemic compounds of formula (I) or compounds of formula (I) having an enantiomeric excess of compounds of formula I-R and agriculturally acceptable salts thereof are harmful to animal organisms, and also That is, harmful arthropods and nematodes, especially insects and acaridae that are difficult to control by other means are highly active.

Furthermore, the present invention relates to and includes the following embodiments: - a composition comprising at least one compound of formula (I) as defined above and below, or a non-racemic compound of formula (I), or a compound of formula (I) with an enantiomeric excess of a compound of formula I-R ; - agricultural and veterinary compositions comprising an amount of at least one compound of formula (I) as defined above and below, or a non-racemic compound of formula (I), or having an enantiomeric excess of formula I-R A compound of formula (I), or an enantiomer, diastereomer or salt thereof; - A method for combating invertebrate pests, infestation or infection by invertebrate pests, the method comprising exposing the pest or its food supply, habitat or breeding grounds to at least one of the above pesticidally effective amounts and a compound of formula (I) as defined below, or a non-racemic compound of formula (I), or a compound of formula (I) having an enantiomeric excess of a compound of formula I-R, or a composition thereof; - a method for controlling invertebrate pests, infestation or infection by invertebrate pests, the method comprising exposing the pest or its food supply, habitat or breeding grounds to at least one of the above pesticidally effective amounts and a compound of formula (I) as defined below, or a non-racemic compound of formula (I), or a compound of formula (I) having an enantiomeric excess of a compound of formula I-R, or comprising at least one compound of formula (I) or a non-racemic compound of formula (I) or a composition of a compound of formula (I) having an enantiomeric excess of a compound of formula I-R; - A method for preventing or preventing invertebrate pests, which comprises combining an invertebrate pest or its food supply, habitat or breeding ground with a substituted pyrimidine of general formula (I) as defined above and below Onium compounds, or non-racemic compounds of formula (I), or compounds of formula (I) having an enantiomeric excess of compounds of formula I-R, or comprising at least one compound of formula (I) as defined above and below, or Compositions of non-racemic compounds of formula (I) or compounds of formula (I) having an enantiomeric excess of compounds of formula I-R, or comprising at least one compound of formula (I) or non-racemic compounds of formula (I) contacting a compound or a composition of a compound of formula (I) having an enantiomeric excess of a compound of formula I-R; - a method for protecting crops, plants, plant propagation material and/or growing plants from attack or infestation by invertebrate pests, comprising administering a pesticidally effective amount of at least one of the formulas as defined above and below ( I) compound, or a non-racemic compound of formula (I), or a compound of formula (I) having an enantiomeric excess of a compound of formula I-R, or comprising at least one compound of formula (I) or a non-racemic compound of formula (I) Racemic compounds or compositions of compounds of formula (I) having an enantiomeric excess of compounds of formula I-R Contact or treatment of crops, plants, plant propagation material and growing plants, or storage of crops, plants, plant propagation material or plant growth soil, material, surface, space, area or water; - a non-therapeutic method for treating or preventing an animal infested or infected with a parasite or protecting an animal from an infestation or infection by a parasite comprising oral, topical or non-therapeutic administration of Enteral administration or administration of a parasiticidally effective amount of a compound of formula (I) as defined above and below, or a non-racemic compound of formula (I), or a compound of formula I-R with an enantiomeric excess (I) compounds, or compositions comprising at least one compound of formula (I) or a non-racemic compound of formula (I) or a compound of formula (I) having an enantiomeric excess of a compound of formula I-R; - a method for the treatment, control, prevention or protection of animals against parasitic infestation or infection by administering or administering to such animals orally, topically or parenterally a A substituted pyrimidinium compound of general formula (I), or a non-racemic compound of formula (I), or a compound of formula (I) having an enantiomeric excess of a compound of formula I-R, or comprising at least one compound of formula (I ) compound or a non-racemic compound of formula (I) or a composition of a compound of formula (I) having an enantiomeric excess of a compound of formula I-R; - Seeds comprising a compound of formula (I) as defined above and below, or a non-racemic compound of formula (I) or having an enantiomeric excess of the formula (I) in an amount of from 0.1 g to 10 kg per 100 kg of seed Compounds of formula (I) of I-R compounds; - a compound of formula (I) as defined above and below, or a non-racemic compound of formula (I), or a compound of formula (I) having an enantiomeric excess of a compound of formula I-R for the protection of growing plants or plants Use of propagating material to protect against infestation or infestation by invertebrate pests; - a compound of formula (I), or a non-racemic compound of formula (I), or a compound of formula (I) having an enantiomeric excess of a compound of formula I-R, or its enantiomers, diastereoisomers Use of salts acceptable in human or veterinary medicine for combating endo- and ectoparasites in animals; - a method for the preparation of a veterinary composition for the treatment, control, prevention or protection of animals from parasitic infestation or infection comprising a parasiticidally effective amount of a compound of formula (I) as defined herein, or A non-racemic compound of formula (I), or a compound of formula (I) having an enantiomeric excess of a compound of formula I-R, or its enantiomers, diastereoisomers and/or veterinarily acceptable Accepted salts are added to carrier compositions suitable for veterinary use; - a compound of formula (I) as defined herein, or a non-racemic compound of formula (I), or a compound of formula (I) having an enantiomeric excess of a compound of formula I-R, or an enantiomer thereof, Use of diastereoisomers and/or veterinarily acceptable salts for the manufacture of a medicament for the treatment, control, prevention or protection of animals from parasitic infestation or infection.

In addition, the present invention also relates to and includes the following embodiments: - a compound of formula (I) as defined herein, or a non-racemic compound of formula (I), or a compound of formula (I) having an enantiomeric excess of a compound of formula I-R, for the control of Oryza sativa in rice Pests, especially invertebrates that are harmful to rice; - a composition comprising at least one compound of formula (I) as defined herein, or a non-racemic compound of formula (I), or a compound of formula (I) having an enantiomeric excess of a compound of formula I-R, for use in In the control of rice pests, especially rice harmful invertebrates; - an agricultural composition comprising an amount of at least one compound of formula (I) as defined herein, or a non-racemic compound of formula (I), or a compound of formula (I) having an enantiomeric excess of formula I-R ) compounds, or their enantiomers, diastereomers or salts as defined above, for the control of rice pests, especially rice harmful invertebrates, in rice; - A method for combating harmful invertebrates of rice, infestation or infection of harmful invertebrates of rice, the method comprising exposing the harmful organism or its food supply, habitat or breeding ground to at least one of a pesticidally effective amount contacting a compound of formula (I) as defined above and below, or a non-racemic compound of formula (I), or a compound of formula (I) having an enantiomeric excess of a compound of formula I-R, or a composition thereof; - a method for controlling harmful invertebrates of rice, invertebrate pest infestation or infection, the method comprising making the pest or its food supply, habitat or breeding ground and at least one of the above pesticidally effective amount A compound of formula (I) as defined hereinbelow, or a non-racemic compound of formula (I), or a compound of formula (I) having an enantiomeric excess of a compound of formula I-R, or comprising at least one compound of formula (I) contacting a compound or a non-racemic compound of formula (I) or a composition of a compound of formula (I) having an enantiomeric excess of a compound of formula I-R; - A method for preventing or preventing harmful invertebrates of rice, which comprises combining harmful invertebrates of rice or their food supply, habitat or breeding ground with a substituted pyrimidine of the general formula (I) as defined above Onium compounds, or non-racemic compounds of formula (I), or compounds of formula (I) having an enantiomeric excess of compounds of formula I-R, or comprising at least one compound of formula (I) as defined above and below, or Contacting a non-racemic compound of formula (I) or a composition of a compound of formula (I) having an enantiomeric excess of a compound of formula I-R; - A method for protecting rice, rice plants, rice plant propagation material and/or growing rice plants from attack or infestation by rice harmful invertebrates, comprising using a pesticidally effective amount of at least one of the above and below A compound of formula (I) as defined, or a non-racemic compound of formula (I), or a compound of formula (I) having an enantiomeric excess of a compound of formula I-R, or comprising at least one compound of formula (I) or Non-racemic compounds of (I) or compositions of compounds of formula (I) having enantiomeric excess of compounds of formula I-R contact or treat rice, rice plants, rice plant propagation material and growing rice plants, or store rice , rice plants, rice plant propagation material or the soil, material, surface, space, area or water on which rice plants grow; - a method for increasing the health of rice plants, especially in paddy fields, comprising using at least one compound of formula (I) as defined herein, or a non-racemic compound of formula (I), or having an enantiomerically Treatment of the compound of formula (I) with excess of the compound of formula I-R; - a method for increasing the yield of rice plants comprising using at least one compound of formula (I) as defined herein, or a non-racemic compound of formula (I), or a compound of formula I-R with enantiomeric excess Formula (I) compound treatment; - Rice seeds comprising a compound of formula (I) as defined above and below, or a non-racemic compound of formula (I), or having an enantiomer in an amount of 0.1 g to 10 kg per 100 kg of seed a compound of formula (I) in excess of a compound of formula I-R; - a compound of formula (I) as defined above and below, or a non-racemic compound of formula (I), or a compound of formula (I) having an enantiomeric excess of a compound of formula I-R for the protection of growing rice plants Or use of rice plant propagation material to protect against attack or infestation by rice harmful invertebrates.

All compounds of the present invention, including (where applicable) their stereoisomers, their tautomers, their salts or their N-oxides and combinations thereof, are particularly suitable for controlling invertebrate pests, especially for controlling Arthropods and nematodes and especially insects. Accordingly, the present invention relates to the use of compounds as disclosed in the present invention for combating or controlling invertebrate pests, especially invertebrate pests of groups of insects, arachnids or nematodes.

The term "compound according to the present invention" or "compound of formula (I)" as used in the present invention refers to and includes a compound as defined herein and/or its stereoisomer, salt, tautomer or N- oxide. The term "compounds of the invention" is understood to be equivalent to the term "compounds according to the invention", thus also encompassing stereoisomers, salts, tautomers or N-oxides of the compounds of formula (I).

As used herein, the terms "compound I-R" or "compound of formula (I-R)" are synonymous.

The term "composition according to the invention" or "composition of the invention" encompasses a compound of formula (I) comprising at least one compound of formula (I) according to the invention as defined above or a compound of formula I-R having an enantiomeric excess ) compounds, thus also including stereoisomers, agriculturally or veterinarily acceptable salts, tautomers or N-oxides of compounds of formula (I).

Compounds of formula (I) exist in meso form. These forms can be represented by different isoelectronic formulas, each with formal positive and negative charges on different atoms (as shown below). The invention extends to all representative isoelectronic structures of the compounds of formula I.

Depending on the substitution pattern, the compounds of the formula (I) possess one or more chiral centers, in which case the compounds exist as mixtures of enantiomers or diastereomers. The present invention provides a single pure enantiomer or pure diastereoisomer of a compound of formula (I) and a mixture thereof, and a pure enantiomer or pure diastereoisomer of a compound of formula (I) or Use according to the invention of mixtures thereof. Suitable compounds of formula (I) also include all possible geometric stereoisomers (cis/trans isomers) and mixtures thereof. Cis/trans isomers may exist relative to olefins, carbon-nitrogen double bonds, or amido groups. The term "stereoisomer" encompasses optical isomers, such as enantiomers or diastereomers, which exist as a result of more than one chiral center in the molecule, as well as geometric isomers (cis/trans isomer). The present invention relates to each possible stereoisomer, ie individual enantiomers or diastereomers, of the compounds of formula (I) and mixtures thereof. Preferred embodiments of specific enantiomers, such as compounds of formula (I-R) and (I-S), are described in more detail below.

Depending on the substitution pattern, the compounds of formula (I) may exist in the form of their tautomers. Accordingly, the present invention also relates to the tautomers of formula (I) and the stereoisomers, salts, tautomers and N-oxides of these tautomers.

The salt of the compound of formula (I) is preferably an agriculturally and/or veterinarily acceptable salt. This can be done by customary methods, eg by reacting the compound with the acid of the anion in question if the compound of formula (I) has a basic function, or by reacting an acidic compound of formula (I) with a suitable base.

Suitable agriculturally or veterinarily useful salts are especially the salts of their cations or the acid addition salts of their acids, the cations and anions of which, respectively, do not have any adverse effect on the action of the compounds according to the invention. Suitable cations are in particular alkali metals, preferably lithium, sodium and potassium; alkaline earth metals, preferably calcium, magnesium and barium; and transition metals, preferably manganese, copper, zinc and iron ions, and ammonium (NH ₄ ⁺ ) And substituted ammonium, wherein one to four hydrogen atoms are replaced by C ₁ -C ₄ alkyl, C ₁ -C ₄ hydroxyalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, hydroxy-C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, phenyl or benzyl substitution. Examples of substituted ammonium ions include methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2- Hydroxyethylammonium, 2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium, in addition, phosphonium ion, Calcite ion, preferably tri(C ₁ -C ₄ alkyl) calcite, and calcite oxide ion, preferably tri(C ₁ -C ₄ alkyl) calcite oxide.

The anions of useful acid addition salts are mainly chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluoro Anions of silicate, hexafluorophosphate, benzoate and C ₁ -C ₄ alkanoic acid, preferably formate, acetate, propionate and butyrate. It can be formed by reacting a compound of formula I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

The term "N-oxide" includes any compound of the invention having at least one tertiary nitrogen atom oxidized to an N-oxide moiety.

The organic moiety groups mentioned above in the variable definitions (eg the term halogen) are collective terms for individual listings of individual group members. In each case, the prefix _Cn - _Cm indicates the possible number of carbon atoms in the group.

An organic moiety may have other substituents attached to it, i.e. an organic moiety may be "substituted by" other moieties (e.g. halogen, fluorine, alkyl), which is also sometimes expressed as "substituted by", but here have the same meaning in context.

"Halogen" denotes in each case fluorine, bromine, chlorine or iodine, especially fluorine, chlorine or bromine.

The term "partially or fully halogenated" means that 1 or more, eg 1, 2, 3, 4 or 5 or all of the hydrogen atoms of a given group have been replaced by halogen atoms, especially by fluorine or chlorine.

As used herein, the term "C _n -C _m alkyl" refers to a branched or unbranched saturated hydrocarbon group having n to m, such as 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, such as methyl Base, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl base, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-di Methylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethyl Butyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2- Methylpropyl, heptyl, octyl, 2-ethylhexyl, nonyl and decyl and their isomers. C ₁ -C ₄ Alkyl means for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethyl ethyl.

The term " _Cn - _Cm haloalkyl" as used herein refers to a straight or branched chain alkyl group (as mentioned above) having n to m carbon atoms, such as 1 to 10, especially 1 to 6 carbon atoms mentioned), wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example C ₁ -C ₄ haloalkyl, such as chloromethyl, bromomethyl, dichloromethane group, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2- Difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and the like. The term C ₁ -C ₁₀ haloalkyl especially includes C ₁ -C ₂ fluoroalkyl, which is synonymous with methyl or ethyl in which 1, 2, 3, 4 or 5 hydrogen atoms are replaced by fluorine atoms, such as fluoromethyl , difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoromethyl. In this case, the alkyl moiety is said to be substituted with halogen or fluorine, and is sometimes also expressed as "substituted by" halogen or fluorine.

Similarly, "C _n -C _m alkoxy" and "C _n -C _m alkylthio" (or C _n -C _m alkylsulfenyl, respectively) refer to any bond in the alkyl group Straight-chain or branched-chain alkyl groups (as above) having n to m carbon atoms, for example 1 to 10, especially 1 to 6 or 1 to 4 carbon atoms, bonded via oxygen (or sulfur linkage, respectively) mentioned). Examples include C ₁ -C ₄ alkoxy, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy and tert-butoxy, Also C ₁ -C ₄ alkylthio, such as methylthio, ethylthio, propylthio, isopropylthio and n-butylthio.

Thus, the term " _Cn - _Cm haloalkoxy" refers to a group having n to m carbon atoms, such as 1 to 10, especially 1 to 6, bonded via an oxygen linkage at any bond in the alkyl group, respectively. straight or branched chain alkyl groups (as mentioned above) of 1 or 1 to 4 carbon atoms, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example C ₁ - _C2 haloalkoxy, such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorine Fluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2 -Difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro -2-fluoroethoxy, 2,2,2-trichloroethoxy and pentafluoroethoxy. Similarly, the term C ₁ -C ₂ fluoroalkoxy refers to a C ₁ -C ₂ fluoroalkyl group bonded to the rest of the molecule via an oxygen atom.

The term "C ₂ -C _m alkenyl" as used herein means a branched or unbranched unsaturated hydrocarbon group having 2 to m, for example, 2 to 10 or 2 to 6 carbon atoms and double bonds in any position , such as vinyl, 1-propenyl, 2-propenyl, 1-methyl-vinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl , 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4 -pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2 -Methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3- Butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1- propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1- Pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2- Methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl Alkenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl Base-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2 -Dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl Alkenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-di Methyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl , 3,3-Dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2- Ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl -1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl.

The term "aryl" as used herein refers to a monocyclic, bicyclic or tricyclic aromatic hydrocarbon group, such as phenyl or naphthyl, especially phenyl (also known as C ₆ H ₅ as a substituent).

The term "ring system" means two or more directly connected rings.

As used herein, the term "C ₃ -C _m cycloalkyl" refers to a 3-membered to m-membered monocyclic saturated cycloaliphatic group, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl , cyclooctyl and cyclodecyl.

As used herein, the term "five-membered or six-membered carbocyclic or heterocyclic ring" refers to a saturated ring, partially unsaturated ring or aromatic ring, which may contain 1, 2, 3 or 4 heteroatoms or heteroatom groups, wherein These heteroatoms (groups) are selected from N (groups substituted by N), O and S (groups substituted by S), and heterocyclic groups as used herein refer to monocyclic groups, and these monocyclic The groups are saturated, partially unsaturated or aromatic (fully unsaturated). A heterocyclic group can be attached to the rest of the molecule via a carbocyclic member or via a nitrogen ring member.

Examples of five- or six-membered carbocyclic or heterocyclic rings include cyclopentane and cyclohexane, cyclohexene, phenyl, pyridyl, 2-tetrahydrofuryl, 3-tetrahydrofuryl, 2-tetrahydrothiophenyl, 3- Tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 2-oxazolidine, 4-oxazolidine, 5-oxazolidine, 3-isoxazolidine, 4-isoxazolidine, 5-isoxazolidine, 2-thiazolidinyl , 4-thiazolidinyl, 5-thiazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1 ,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4- Triazolidine-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidine-2- Base, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 2-piperidinyl, 3- Piperidinyl, 4-piperidinyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperidinyl Azinyl, 1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl, 2-morpholinyl, 3-morpholinyl, 2-thiomorpholinyl Linyl, 3-thiomorpholinyl, 1-oxothiomorpholin-2-yl, 1-oxothiomorpholin-3-yl, 1,1-dioxothiomorpholin-2-yl Lin-2-yl, 1,1-dioxothiomorpholin-3-yl and the like.

Examples of 5-membered or 6-membered partially unsaturated heterocyclic groups or heterocycles include: 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,4-dihydrofuran- 2-yl, 2,4-dihydrofuran-3-yl, 2,3-dihydrothiophen-2-yl, 2,3-dihydrothiophen-3-yl, 2,4-dihydrothiophen-2- Base, 2,4-dihydrothiophen-3-yl, 2-pyrroline-2-yl, 2-pyrroline-3-yl, 3-pyrroline-2-yl, 3-pyrroline-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin -4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2 -isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4 -isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazole-1- Base, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol- 5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazole Azol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-di Hydrogen pyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3 -Dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3 ,4-Dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl , 2-, 3-, 4-, 5- or 6-dihydropyridyl or tetrahydropyridyl, 3-dihydropyridazinyl or tetrahydropyridazinyl, 4-dihydropyridazinyl or tetrahydropyridyl Azinyl, 2-dihydropyrimidinyl or tetrahydropyrimidinyl, 4-dihydropyrimidinyl or tetrahydropyrimidinyl, 5-dihydropyrimidinyl or tetrahydropyrimidinyl, dihydropyrazinyl or tetrahydropyrazinyl , 1,3,5-dihydrotriazine or tetrahydrotriazin-2-yl, 1,2,4-dihydrotriazine or tetrahydrotriazin-3-yl.

Examples of 5-membered or 6-membered aromatic heterocyclic groups (heteroaryl) or heteroaryl rings are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3- Pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5 -thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazol-2-yl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-pyridazinyl, 4- pyrazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.

Unless otherwise specified, the term "at least XX%" means > XX% to < 100%, eg at least 55% means > 55% to < 100%.

The term "non-racemic compound of formula (I)" refers to a compound of formula (I) wherein its R- and S-enantiomers are not present in equal amounts.

The term "enantiomeric excess" indicates the excess of an enantiomer in a mixture of enantiomers and is calculated according to the following formula: ee = [│m ₁ ─ m ₂ │/ (m ₁ + m ₂ )] × 100% ee : enantiomeric excess m ₁ : fraction of enantiomer 1 m ₂ : fraction of enantiomer 2

As used herein and unless otherwise indicated, the term "enantiomer" means each individual optically active form of a compound of the invention.

As used herein, the term "having enantiomeric excess" means that the enantiomer having "enantiomeric excess" with respect to the term used has an enantiomeric excess compared to the other enantiomer The mixture of enantiomers is present in excess, preferably in an amount of at least 60%, preferably at least 80%, more preferably at least 95%, most preferably at least 98% of the mixture of enantiomers. For example, the term "compound of formula I-1 having an enantiomeric excess of compound I-R-1" means that compound I-R-1 is in enantiomeric excess compared to compound I-S-1, preferably at least 60%. , preferably at least 80%, more preferably at least 95%, most preferably at least 98% of the compound of formula I-1 present.

Compounds according to the invention can be prepared as described in WO2014/167084 or as follows. The preparation of the above compound of formula (I) allows it to be obtained as a mixture of isomers. If desired, they can be resolved by methods customary for the purpose, such as crystallization or chromatography, also for optically active adsorbates, to give the pure isomers.

Agronomically acceptable salts of compounds I can be formed in customary manner, for example by reaction with an acid of the anion in question.

Compounds of formula (I) can be prepared from appropriately substituted compounds (III) analogously to the method described by Holyoke et al. in WO 2009/099929 (Scheme 1).

化合物(III)可藉由例如Brian R. Dixon等人在US 6, 353, 006中所述之方法由例如2-氯乙胺類化合物(V)製備，及藉由與其類似之方法，用經適當取代之反應物製備。plan 1

Compound (III) can be prepared from, for example, 2-chloroethylamine compound (V) by the method described in US 6,353,006 by, for example, Brian R. Dixon et al., and by a method similar thereto, using Preparation of appropriately substituted reactants.

2-氯乙胺化合物(V)又可例如藉由還原亞磺醯亞胺來獲得，如Denolf, Bram等人, Journal of Organic Chemistry, 72(9), 3211-3217; 2007中所例示。Scenario 2

2-Chloroethylamine compound (V) can be obtained, for example, by reducing sulfenimine, as exemplified in Denolf, Bram et al., Journal of Organic Chemistry, 72(9), 3211-3217; 2007.

化合物(VII)係由α-鹵基-酮獲得，其為熟習此項技術者所熟知。Option 3

Compound (VII) is obtained from α-halo-ketones, which are well known to those skilled in the art.

其中 W為鹵素、O-對甲苯磺醯基、O-甲磺醯基或O-三氟甲磺醯基； Het如式I化合物中所定義； 與M² OR^AC 反應，其中M² 係選自鋰、鈉、鉀、鋁、鋇、銫、鈣及鎂；R^AC 為C(=O)C₁ -C₄ 烷基； 以獲得式IV化合物，

其中Het及R^AC 如本文所定義； (B) 在酸或鹼存在下水解如本文所定義之式IV化合物，以獲得式V化合物，

其中Het如式IV化合物中所定義； (C) 使式V化合物與X² SO₂ NH₂ 反應，其中X² 為鹵素， 以獲得式VI化合物

其中Het如式V化合物中所定義， (D) 式VI化合物在氫化催化劑MXLn， 其中 M為來自元素週期表第VIII族至第XII族之過渡金屬； X為陰離子； Ln為Ln1或Ln2， 其中 Ln1為式Ln1之對掌性配體

其中 C*為S或R-組態之不對稱碳原子； R¹⁰ 為OH或NH-SO₂ -R¹¹ ；其中 R¹¹ 為未經取代或經鹵素、C₁ -C₁₀ 烷基、C₁ -C₄ 烷氧基、C₃ -C₆ 環烷基、SO₃ H或SO₃ Na取代之芳基， 或 C₁ -C₁₀ 全氟烷基或R¹³ R¹⁴ N，其中R¹³ 及R¹⁴ 獨立地表示未經取代或經C₆ -C₁₀ 芳基取代之C₁ -C₁₀ 烷基，或R¹³ 及R¹⁴ 表示C₆ -C₁₀ 環烷基； R¹² 獨立地表示芳基或C₆ -C₁₀ 環烷基環，其中該環未經取代或彼此獨立地經鹵素、C₁ -C₁₀ 烷基、C₁ -C₄ 烷氧基、C₃ -C₆ 環烷基、SO₃ H或SO₃ Na取代，或兩個R¹² 連接在一起以形成3員至6員碳環或5員至10員部分不飽和碳環； Ln2為對掌性磷配體； 及選自a) N(R)₃ ，其中R為H或C₁ -C₆ 烷基，及HCOOH之混合物，b) HCOONa，及c)異丙醇及t -BuOK或t -BuONa或t -BuOLi之混合物的氫源存在下氫化； 以獲得式VII化合物

其中 C*為S或R-組態之不對稱碳原子； Het如式VI化合物中所定義， (E) 使式VII化合物，

其中 C*為S或R-組態之不對稱碳原子； Het如本文所定義； 與R¹ NCS在鹼存在下反應，其中R¹ 為C₁ -C₄ 烷基、C₃ -C₆ 環烷基、C₂ -C₄ 烯基或-CH₂ -苯基，該等基團未經取代或經鹵素或C₁ -C₄ 烷基取代； 以獲得式VIII化合物，

其中 C*及Het如式VII化合物中所定義； R¹ 如本文所定義， (F) 使如本文所定義之式VIII化合物與式IX化合物反應

其中， LG為選自鹵素、OR^u 或SR^u 之離去基；其中 R^u 為鹵素、C₁ -C₆ 烷基或芳基，其未經取代或經鹵素取代； R² 如式I化合物中所定義； 以獲得如本文所定義之具有對映異構體過量之式I化合物。Compounds of formula I with enantiomeric excess can be prepared by the methods described below or in analogy to the methods described in the Examples section: Compounds of formula I with enantiomeric excess can be prepared by comprising at least The method preparation of step: (A) make formula III compound

Wherein W is halogen, O-p-toluenesulfonyl, O-methylsulfonyl or O-trifluoromethanesulfonyl; Het is as defined in the compound of formula I; reacts with M ² OR ^AC , wherein M ² is selected from From lithium, sodium, potassium, aluminum, barium, cesium, calcium and magnesium; R ^AC is C (=O) C ₁ -C ₄ alkyl; To obtain the compound of formula IV,

wherein Het and R ^AC are as defined herein; (B) hydrolyzing a compound of formula IV as defined herein in the presence of an acid or base to obtain a compound of formula V,

wherein Het is as defined in the compound of formula IV; (C) reacting the compound of formula V with X ² SO ₂ NH ₂ , wherein X ² is halogen, to obtain the compound of formula VI

Wherein Het is as defined in the compound of formula V, (D) the compound of formula VI is in the hydrogenation catalyst MXLn, wherein M is a transition metal from Group VIII to Group XII of the Periodic Table of Elements; X is an anion; Ln is Ln1 or Ln2, wherein Ln1 is the chiral ligand of formula Ln1

Where C* is an asymmetric carbon atom in S or R-configuration; R ¹⁰ is OH or NH-SO ₂ -R ¹¹ ; where R ¹¹ is unsubstituted or halogenated, C ₁ -C ₁₀ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₆ cycloalkyl, SO ₃ H or SO ₃ Na substituted aryl, or C ₁ -C ₁₀ perfluoroalkyl or R ¹³ R ¹⁴ N, wherein R ¹³ and R ¹⁴ independently represents C ₁ -C ₁₀ alkyl unsubstituted or substituted by C ₆ -C ₁₀ aryl, or R ¹³ and R ¹⁴ represent C ₆ -C ₁₀ cycloalkyl; R ¹² independently represents aryl or C ₆ -C ₁₀ cycloalkyl ring, wherein the ring is unsubstituted or independently of each other by halogen, C ₁ -C ₁₀ alkyl, C ₁ -C ₄ alkoxy, C ₃ -C ₆ cycloalkyl, SO ₃ H or SO ₃ Na is substituted, or two R ¹² are connected together to form a 3-6-membered carbocycle or a 5-10-membered partially unsaturated carbocycle; Ln2 is a pair of chiral phosphorus ligands; and is selected from a ) N(R) ₃ , wherein R is H or C ₁ -C ₆ alkyl, and a mixture of HCOOH, b) HCOONa, and c) a mixture of isopropanol and t -BuOK or t -BuONa or t -BuOLi Hydrogenation in the presence of a hydrogen source; to obtain a compound of formula VII

Wherein C* is an asymmetric carbon atom of S or R-configuration; Het is as defined in the compound of formula VI, (E) makes the compound of formula VII,

wherein C* is an asymmetric carbon atom of S or R-configuration; Het is as defined herein; reacts with R ¹ NCS in the presence of a base, wherein R ¹ is C ₁ -C ₄ alkyl, C ₃ -C ₆ ring Alkyl, C ₂ -C ₄ alkenyl or -CH ₂ -phenyl, these groups are unsubstituted or substituted by halogen or C ₁ -C ₄ alkyl; to obtain the compound of formula VIII,

wherein C* and Het are as defined in the compound of formula VII; R ¹ is as defined herein, (F) reacting a compound of formula VIII as defined herein with a compound of formula IX

Among them, LG is a leaving group selected from halogen, OR ^u or SR ^u ; wherein R ^u is halogen, C ₁ -C ₆ alkyl or aryl, which is unsubstituted or substituted by halogen; R ² is as a compound of formula I as defined in; to obtain a compound of formula I having an enantiomeric excess as defined herein.

Preferably in one embodiment of the present invention, R ¹ is C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₄ alkenyl.

In another embodiment, R ¹ is C ₁ -C ₄ alkyl. In another embodiment, R ¹ is methyl or ethyl.

In one embodiment of the present invention, R ² is phenyl, pyridyl or thiophene, which may be unsubstituted, partially or fully substituted by R ^2a .

In another embodiment, R ² is phenyl, which may be unsubstituted, partially or fully substituted by R ^2a , wherein R ^2a is halogen, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ haloalkoxy group, OR ^c , C(=O)OR ^c , C(=O)NR ^b R ^c , phenyl or pyridyl, which can be modified by halogen, C ₁ -C ₆ haloalkyl or C ₁ -C ₆ haloalkane Oxygen substitution.

In another embodiment, R ² is phenyl, which may be unsubstituted, partially or fully substituted with halogen, C ₁ -C ₄ alkyl, or C ₁ -C ₃ haloalkyl.

In another embodiment, R ^is phenyl, which may be unsubstituted, partially or fully substituted with trifluoromethyl or halogen (preferably chlorine);

In another embodiment, R ² is phenyl, 3,5-dichlorophenyl, 3-trifluoromethylphenyl.

In another embodiment, ^R2 is phenyl.

In another embodiment, R ² is 3,5-dichlorophenyl.

In another embodiment, R ² is 3-trifluoromethylphenyl.

In one embodiment of the present invention, Het is a five- or six-membered carbocyclic or heterocyclic aromatic ring.

In one embodiment of the invention, Het is D-2.

In one embodiment of the present invention, Het is D-2, wherein R ^a is halogen, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio; n is 1 or 2.

In one embodiment of the present invention, Het is selected from D-1, D-2 and D-3, wherein R ^a is chlorine, and n is 1.

In another embodiment, Het is D-1a, D-2a and D-3a:

In another embodiment, Het is D-1a.

In another embodiment, Het is D-2a.

In another embodiment, Het is D-3a.

In one embodiment of the present invention, the compound of formula (I) is one of the following compounds I-1 to I-6:

In one embodiment of the present invention, the compound of formula (I) is compound I-1.

In one embodiment of the present invention, the compound of formula (I) is compound I-2.

In one embodiment of the present invention, the compound of formula (I) is compound I-3.

In one embodiment of the present invention, the compound of formula (I) is compound I-4.

In one embodiment of the present invention, the compound of formula (I) is compound I-5.

In one embodiment of the present invention, the compound of formula (I) is compound I-6.

In one embodiment of the present invention, the compound of formula (I) has the following stereochemistry as in formula (IR):

Compounds of formula (I-R) show higher pesticidal efficacy compared to their stereoisomers of formula (I-S), as demonstrated by biological examples. The selectivity of compound (I-R) for biological targets such as enzymes or receptors differs from the selectivity of compound (I-S).

In another embodiment, compounds according to the present invention have stereochemistry as in formula (IR), and R ¹ is C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₄ alkenyl Group, R ¹ is preferably C ₁ -C ₄ alkyl, R ¹ is preferably methyl or ethyl.

In another embodiment, the compound according to the present invention has the stereochemistry as in formula (IR), and R ² is phenyl, pyridyl or thiophene, which may be unsubstituted, partially or fully substituted by R ^2a , wherein R ^2a is halogen, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ haloalkoxy, OR ^c , C(=O)OR ^c , C(=O)NR ^b R ^c , phenyl or pyridyl , which may be substituted by halogen, C ₁ -C ₆ haloalkyl or C ₁ -C ₆ haloalkoxy.

In another embodiment, compounds according to the present invention have stereochemistry as in formula (IR), and R ² is phenyl, which may be unsubstituted, partially or fully substituted with R ^2a as defined above.

In another embodiment, the compound according to the present invention has the stereochemistry as in formula (IR), and R ² is phenyl, which can be unsubstituted, halogen, C ₁ -C ₄ alkyl or C ₁ - C ₃ haloalkyl is partially or fully substituted; preferably, R ² is phenyl, which may be unsubstituted, partially or fully substituted with trifluoromethyl or halogen (preferably chlorine).

In another embodiment, compounds according to the present invention have stereochemistry as in formula (IR), and R ² is phenyl, 3,5-dichlorophenyl, 3-trifluoromethylphenyl.

In another embodiment, compounds according to the invention have the stereochemistry as in formula (IR), and ^R2 is phenyl.

In another embodiment, compounds according to the present invention have the stereochemistry as in formula (IR), and R ² is 3,5-dichlorophenyl.

In another embodiment, compounds according to the present invention have the stereochemistry as in formula (IR), and R ² is 3-trifluoromethylphenyl.

In another embodiment of the present invention, Het is D-2.

In another embodiment of the present invention, Het is D-2, wherein R ^a is halogen, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio; n is 1 or 2.

In another embodiment, the compound according to the present invention has the stereochemistry as in formula (IR), and Het is selected from D-1, D-2 and D-3, wherein ^Ra is chlorine and n is 1.

In another embodiment, the compound according to the present invention has the stereochemistry as in formula (I-R), and Het is D-1a, D-2a or D-3a.

In another embodiment, the compound according to the present invention has the stereochemistry as in formula (I-R), and Het is D-1a.

In another embodiment, the compound according to the present invention has the stereochemistry as in formula (I-R), and Het is D-2a.

In another embodiment, the compound according to the present invention has the stereochemistry as in formula (I-R), and Het is D-3a.

In one embodiment of the present invention, the compound of formula (I) is one of the following compounds IR-1 to IR-6:

In one embodiment of the present invention, the compound of formula (I) is compound I-R-1.

In one embodiment of the present invention, the compound of formula (I) is compound I-R-2.

In one embodiment of the present invention, the compound of formula (I) is compound I-R-3.

In one embodiment of the present invention, the compound of formula (I) is compound I-R-4.

In one embodiment of the present invention, the compound of formula (I) is compound I-R-5.

In one embodiment of the present invention, the compound of formula (I) is compound I-R-6.

In one embodiment of the present invention, the compound of formula (I) refers to the compound of formula (I) having enantiomeric excess formula (IR), wherein the variables Het, R ¹ and R ² are as in the compound of formula (I) defined.

In one embodiment of the invention, the compound of formula (I) refers to the compound of formula (I) having at least 55% enantiomeric excess of formula (I-R).

In one embodiment of the invention, the compound of formula (I) refers to the compound of formula (I) having at least 60% enantiomeric excess of formula (I-R).

In one embodiment of the invention, the compound of formula (I) refers to the compound of formula (I) having at least 65% enantiomeric excess of formula (I-R).

In one embodiment of the invention, the compound of formula (I) refers to the compound of formula (I) having at least 70% enantiomeric excess of formula (I-R).

In one embodiment of the invention, the compound of formula (I) refers to the compound of formula (I) having at least 75% enantiomeric excess of formula (I-R).

In one embodiment of the invention, the compound of formula (I) refers to the compound of formula (I) having at least 80% enantiomeric excess of formula (I-R).

In one embodiment of the invention, the compound of formula (I) refers to the compound of formula (I) having at least 85% enantiomeric excess of formula (I-R).

In a preferred embodiment of the present invention, the compound of formula (I) refers to the compound of formula (I) having at least 90% enantiomeric excess of formula (I-R).

In another preferred embodiment of the present invention, the compound of formula (I) refers to the compound of formula (I) having at least 95% enantiomeric excess of formula (I-R).

In another preferred embodiment of the present invention, the compound of formula (I) refers to the compound of formula (I) having at least 98% enantiomeric excess of formula (I-R).

In another preferred embodiment of the present invention, the compound of formula (I) refers to the compound of formula (I) having at least 99% enantiomeric excess of formula (I-R).

In another embodiment of the present invention, the compound of formula (I) has the following stereochemistry as in formula (IS):

In another embodiment, the compound according to the present invention has the stereochemistry as in formula (IS), and R ¹ is C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₄ alkenyl Group, R ¹ is preferably C ₁ -C ₄ alkyl, R ¹ is preferably methyl or ethyl.

In another embodiment, the compound according to the present invention has the stereochemistry as in formula (IS), and R ² is phenyl, pyridyl or thiophene, which may be unsubstituted, partially or fully substituted by R ^2a , wherein R ^2a is halogen, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ haloalkoxy, OR ^c , C(=O)OR ^c , C(=O)NR ^b R ^c , phenyl or pyridyl , which may be substituted by halogen, C ₁ -C ₆ haloalkyl or C ₁ -C ₆ haloalkoxy.

In another embodiment, the compound according to the present invention has the stereochemistry as in formula (IS), and R ² is phenyl, which may be unsubstituted, partially or fully substituted with R ^2a as defined above.

In another embodiment, the compound according to the present invention has the stereochemistry as in formula (IS), and R ² is phenyl, which can be unsubstituted, halogen, C ₁ -C ₄ alkyl or C ₁ - C ₃ haloalkyl is partially or fully substituted; preferably, R ² is phenyl, which may be unsubstituted, partially or fully substituted with trifluoromethyl or halogen (preferably chlorine).

In another embodiment, compounds according to the present invention have stereochemistry as in formula (IS), and R ² is phenyl, 3,5-dichlorophenyl, 3-trifluoromethylphenyl.

In another embodiment, compounds according to the invention have the stereochemistry as in formula (IS), and R ² is phenyl.

In another embodiment, compounds according to the invention have the stereochemistry as in formula (IS), and R ² is 3,5-dichlorophenyl.

In another embodiment, compounds according to the invention have the stereochemistry as in formula (IS), and R ² is 3-trifluoromethylphenyl.

In another embodiment, the compound according to the present invention has the stereochemistry as in formula (IS), and Het is selected from D-1, D-2 and D-3, wherein ^Ra is chlorine and n is 1.

In another embodiment, the compound according to the present invention has the stereochemistry as in formula (I-S), and Het is D-1a, D-2a or D-3a;

In another embodiment, the compound according to the present invention has the stereochemistry as in formula (I-S), and Het is D-1a.

In another embodiment, the compound according to the present invention has the stereochemistry as in formula (I-S), and Het is D-2a.

In another embodiment, the compound according to the present invention has the stereochemistry as in formula (I-S), and Het is D-3a.

Compounds of formula (I) with enantiomeric excess formula (I-R) show higher pesticidal efficacy compared to racemic mixtures or compounds of formula (I) with enantiomeric excess formula (I-S) , as demonstrated by biological examples.

In another embodiment, the compound according to the invention is a compound of formula (I) having enantiomeric excess formula (IR), wherein R ¹ is C ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkane Group, C ₂ -C ₄ alkenyl, R ¹ is preferably C ₁ -C ₄ alkyl, R ¹ is preferably methyl or ethyl.

In another embodiment, the compound according to the present invention is a compound of formula (I) having enantiomeric excess formula (IR), wherein R ² is phenyl, pyridyl or thiophene, which may be unsubstituted, modified R ^2a is partially or fully substituted, wherein R ^2a is halogen, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ haloalkoxy, OR ^c , C(=O)OR ^c , C(=O)NR ^b R ^c , phenyl or pyridyl, which may be substituted by halogen, C ₁ -C ₆ haloalkyl or C ₁ -C ₆ haloalkoxy.

In another embodiment, the compound according to the present invention is a compound of formula (I) having enantiomeric excess formula (IR), wherein ^R is phenyl, which may be unsubstituted, as defined above R ^2a is partially or fully substituted.

In another embodiment, the compound according to the present invention is a compound of formula (I) having enantiomeric excess formula (IR), wherein R ² is phenyl, which may be unsubstituted, halogenated, C ₁ - C ₄ alkyl or C ₁ -C ₃ haloalkyl is partially or fully substituted; preferably, R ^is phenyl, which may be unsubstituted, partially or fully substituted with trifluoromethyl or halogen (preferably chlorine) .

In another embodiment, the compound according to the invention is a compound of formula (I) having enantiomeric excess formula (IR), wherein ^R is phenyl, 3,5-dichlorophenyl, 3-tri Fluoromethylphenyl.

In another embodiment, the compound according to the invention is a compound of formula (I) having enantiomeric excess formula (IR), wherein R ² is phenyl.

In another embodiment, the compound according to the invention is a compound of formula (I) having enantiomeric excess formula (IR), wherein R ² is 3,5-dichlorophenyl.

In another embodiment, the compound according to the invention is a compound of formula (I) having enantiomeric excess formula (IR), wherein R ² is 3-trifluoromethylphenyl.

In another embodiment, the compound according to the present invention is a compound of formula (I) having enantiomeric excess formula (IR), wherein Het is selected from D-1, D-2 and D-3, wherein R ^a is chlorine, and n is 0 or 1.

In another embodiment, the compound according to the invention is a compound of formula (I) having enantiomeric excess formula (I-R), wherein Het is D-2;

In another embodiment, the compound according to the invention is a compound of formula (I) having enantiomeric excess formula (IR), wherein Het is D-2, wherein R ^a is halogen, C ₁ -C ₄ halogen Alkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio; n is 1 or 2.

In another embodiment, the compound according to the invention is a compound of formula (I) having enantiomeric excess formula (I-R), wherein Het is D-1a, D-2a or D-3a.

In another embodiment, the compound according to the invention is a compound of formula (I) having enantiomeric excess formula (I-R), wherein Het is D-1a.

In another embodiment, the compound according to the invention is a compound of formula (I) having enantiomeric excess formula (I-R), wherein Het is D-2a.

In another embodiment, the compound according to the invention is a compound of formula (I) having enantiomeric excess formula (I-R), wherein Het is D-3a.

In one embodiment of the invention, the compound of formula (I) is selected from compounds I-1 to I-6 having enantiomeric excess of R-enantiomer compounds I-R-1 to I-R-6, respectively.

In one embodiment of the present invention, the compound of formula (I) is compound I-1 having an enantiomeric excess of compound I-R-1.

In one embodiment of the invention, the compound of formula (I) is compound 1-2 having an enantiomeric excess of compound I-R-2.

In one embodiment of the invention, the compound of formula (I) is compound 1-3 having an enantiomeric excess of compound I-R-3.

In one embodiment of the invention, the compound of formula (I) is compound 1-4 having an enantiomeric excess of compound I-R-4.

In one embodiment of the invention, the compound of formula (I) is compound 1-5 having an enantiomeric excess of compound I-R-5.

In one embodiment of the invention, the compound of formula (I) is compound 1-6 having an enantiomeric excess of compound I-R-6.

In one embodiment of the present invention, the compound of formula (I) is one of the following compounds IS-1 to IS-6:

In one embodiment of the present invention, the compound of formula (I) is compound I-S-1.

In one embodiment of the present invention, the compound of formula (I) is compound I-S-2.

In one embodiment of the present invention, the compound of formula (I) is compound I-S-3.

In one embodiment of the present invention, the compound of formula (I) is compound I-S-4.

In one embodiment of the present invention, the compound of formula (I) is compound I-S-5.

In one embodiment of the present invention, the compound of formula (I) is compound I-S-6.

In one embodiment of the present invention, the compound of formula (I) refers to the compound of formula (I) having enantiomeric excess formula (I-R), wherein formula (I-R) is present in an amount of ≥ 55% to ≤ 100% And formula (I-S) is present in an amount of ≤45% to ≥0%.

In one embodiment of the present invention, the compound of formula (I) refers to the compound of formula (I) having enantiomeric excess formula (I-R), wherein formula (I-R) is present in an amount of ≥ 60% to ≤ 100% And the formula (I-S) is present in an amount of ≤40% to ≥0%.

In one embodiment of the present invention, the compound of formula (I) refers to the compound of formula (I) having enantiomeric excess formula (I-R), wherein formula (I-R) is present in an amount of ≥ 65% to ≤ 100% And the formula (I-S) is present in an amount of ≤35% to ≥0%.

In one embodiment of the present invention, the compound of formula (I) refers to the compound of formula (I) having enantiomeric excess formula (I-R), wherein formula (I-R) is present in an amount of ≥ 70% to ≤ 100% And the formula (I-S) is present in an amount of ≤30% to ≥0%.

In one embodiment of the present invention, the compound of formula (I) refers to the compound of formula (I) having enantiomeric excess formula (I-R), wherein formula (I-R) is present in an amount of ≥ 75% to ≤ 100% And formula (I-S) is present in an amount of ≤25% to ≥0%.

In one embodiment of the present invention, the compound of formula (I) refers to the compound of formula (I) having enantiomeric excess formula (I-R), wherein formula (I-R) is present in an amount of ≥ 80% to ≤ 100% And the formula (I-S) is present in an amount of ≤20% to ≥0%.

In one embodiment of the present invention, the compound of formula (I) refers to the compound of formula (I) having enantiomeric excess formula (I-R), wherein formula (I-R) is present in an amount of ≥ 85% to ≤ 100% And formula (I-S) is present in an amount of ≤ 15% to ≥ 0%.

In another embodiment of the present invention, the compound of formula (I) refers to the compound of formula (I) having enantiomeric excess formula (I-R), wherein the amount of formula (I-R) is ≥ 90% to ≤ 100% exists and the formula (I-S) is present in an amount of ≤10% to ≥0%.

In another embodiment of the present invention, the compound of formula (I) refers to the compound of formula (I) having enantiomeric excess formula (I-R), wherein the amount of formula (I-R) is ≥ 95% to ≤ 100% exists and the formula (I-S) is present in an amount of ≤5% to ≥0%.

In another embodiment of the present invention, the compound of formula (I) refers to the compound of formula (I) having enantiomeric excess formula (I-R), wherein formula (I-R) is ≥ 98% to ≤ 100%, more Preferably present in an amount of ≥99% to ≤100%, and formula (I-S) is present in an amount of ≤2% to ≥0%, preferably ≤1% to ≥0%.

mixture A typical problem that arises in the field of pest control is the need to reduce the dosage rate of an active ingredient in order to reduce or avoid adverse environmental or toxicological effects, while still allowing effective pest control.

Another problem encountered relates to the need to have available pest control agents effective against a broad spectrum of pests.

There is also a need for pest control agents that combine knockdown activity and long-term control, ie both fast acting and long lasting.

A further difficulty associated with the use of pesticides is that the repeated and exclusive application of individual pesticidal compounds leads in many cases to rapid selection of pests which have developed natural or adaptive resistance to the active compound in question. Accordingly, there is a need for pest control agents that help prevent or overcome pesticide-induced tolerance.

Furthermore, there is a need for pesticide compounds or combinations of compounds which improve plants when applied, which result in "plant health", "vigor of plant propagation material" or "increased plant yield".

It is therefore an object of the present invention to provide an agricultural combination which solves one or more of the problems discussed, such as - reduced dose rate, - enhanced activity spectrum, - combined knockdown activity with long-term control, - improved resistance management, - Improved plant health; - Improve the vigor of plant propagation material, also known as seed vigor; - Increase plant production

It was therefore an object of the present invention to provide pesticidal mixtures which solve at least one of the problems discussed, such as reduced dose rates, enhanced activity spectrum or combined knockdown activity with long-term control, or with regard to resistance management.

It has been found that this object is partly or fully achieved by combinations of active compounds as defined herein.

Thus, in a particular embodiment of the invention, the compound according to the invention is admixed with at least one other active ingredient.

As used herein, the term "mixture of the invention" or "mixture according to the invention" refers to a compound of formula (I) comprising a compound of formula (I) as defined above or having an enantiomeric excess of formula (I-R) Compound, which is also referred to as "compound of formula (I)" or "compound I" or "compound of formula (I)", and compound (II) as defined below, which is also referred to as "compound of formula II" or "compound of formula (I)" Compound II" mixture.

Compounds of formula I or non-racemic compounds of formula (I) or compounds of formula (I) in excess of enantiomers, and compound II are understood to include salts, tautomers, stereoisomers and N- oxide.

In one embodiment of the invention, the invention relates to a mixture comprising: (1) at least one compound of formula (I) or a non-racemic compound of formula (I) as defined herein or having an enantiomer Compounds of formula (I), enantiomers, salts, tautomers, stereoisomers and N-oxides of compounds of formula (IR) or (IS) in excess, and (2) at least one compound II , which is selected from the following group: M.1 Acetylcholinesterase (AChE) inhibitors: M.1A carbamates, such as aldicarb, alanycarb, dimecarb (bendiocarb), benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, butyl carbosulfan, insecticide Ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, methiocarb (metolcarb), oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, methacarb (xylylcarb) and triazamate; or M.1B organophosphates, such as acephate, azamethiphos, azinphos-ethyl, methyl triazine Azinphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, chlorpyrifos-methyl (coumaphos), cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dameton Dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos , fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, O-(methoxy-amino Thio-phosphoryl) isopropyl salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, methidathion (mevinphos), monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion- methyl), phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, methyl yatson ( pirimiphos-methyl), profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, moth control Sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, three Trichlorfon and vamidothion; M.2. GABA-gated chloride channel antagonists: M.2A cyclodiene organochlorine compounds, such as endosulfan or chlordane; or M.2B Phenylpyrazoles (fiproles) (phenylpyrazoles), such as ethiprole, fipronil, flufiprole, pyrazine and pyrafluprole Pyriprole; M.3 M.3A Pyrethroid sodium channel modulators such as acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, Bifenning (bifenthrin) (especially κ-bifenning), Baiyalenin (bioallethrin), Baiyalenin S-cyclopentenyl, resmethrin (bioresmethrin), promethrin ( cycloprothrin), cyfluthrin, β-saifuning, cyhalothrin, λ-sailuoning, γ-sailuoning, cypermethrin, α-saiminging, β- Cyphenin, θ-cyphenin, ζ-cyphenothrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox ), fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, seven Heptafluthrin, imiprothrin, meperfluthrin, metofluthrin, momfluothrin (especially ε-mofluthrin), perfluthrin Permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, Silafluofen, tefluthrin (especially kappa-tefluthrin), tetramethylfluthrin, tetramethrin, tralomethrin, and bifluthrin (transfluthrin); or M.3B sodium channel modulators such as DDT or methoxychlor; M.4 Nicotinic acetylcholine receptor agonists (nAChR): M.4A neonicotinoid analogs ( neonicotinoids), such as acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid ( thiacloprid) and thiamethoxam; or compound M.4A.1 4,5-dihydro-N-nitro-1-(2-oxiranylmethyl)-1H-imidazol-2-amine , M.4A.2: (2E-)-1-[(6-chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidene carboxamidine; or M4.A.3: 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[ 1,2-a]pyridine; or M.4B Nicotine; M.4C Sulfoxaflor; M.4D Flupyradifurone; M.4E Triflumezopyrim; M .5 Nicotinic acetylcholine receptor ectopic activators: spinosyns, such as spinosad or spinetoram; M.6 avermectins and chloride channel activators of milbemycins, such as abamectin, emamectin benzoate, ivermectin, lepimectin, or M.7 Juvenile hormone mimetics, such as M.7A Juvenile hormone analogs hydroprene, kinoprene and methoprene; or M.7B Fenoxycarb, or M.7C pyriproxyfen; M.8 various non-specific (multi-site) inhibitors, such as M.8A alkyl halides, such as methyl bromide and other alkanes Base halide, M.8B chloropicrin (chloropicrin), M.8C sulfuryl fluoride, M.8D borax or M.8E tartar emetic; M.9 stringer TRPV channel modulator, such as M. 9B pymetrozine; pyrifluquinazon; M.10 Mite growth inhibitors such as M.10A clofentezine, hexythiazox and diflovidazin, or M.10B etoxazole; M.12 mitochondrial ATP synthase inhibitors, such as M.12A diafenthiuron or M.12B organotin insecticides, such as azocyclotin ), cyhexatin or fenbutatin oxide, M.12C propargite or M.12D tetradifon; M.13 Oxidative phosphorylation by disrupting the proton gradient Decouplers such as chlorfenapyr, DNOC or sulfluramid; M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers such as nereistoxin analogues bensultap, cartap hydrochloride, thiocyclam or thiosultap sodium; M.15 Chitin biosynthesis type 0 inhibitors, such as benzoyl urea Classes such as bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron (lufenuron), novaluron, noviflumuron, teflubenzuron or triflumuron; M.16 Inhibitors of chitin biosynthesis type 1, such as ibufenuron ( buprofezin); M.17 Diptera insect molting disruptors, such as cyromazine; M.18 Ecdysone receptor agonists, such as dihydrazine, such as methoxyfenozide, defenox ( tebufenozide), halofenozide, fufenozide or chromafenozide; M.19 Octopamine receptor agonists such as amitraz; M.20 Mitochondria Complex III electron transport inhibitors, such as M.20A hydramethylnon, M.20B acequinocyl, M.20C fluacrypyrim; or M.20D bifenazate; M .21 Mitochondrial complex I electron transport inhibitors such as M.21A METI acaricides and insecticides such as fenazaquin, fenpyroximate, pyrimidifen, bidar Ben (pyridaben), tebufenpyrad or tolfenpyrad, or M.21B rotenone; M.22 voltage-dependent sodium channel blocker, such as M.22A indoxacarb , M.22B metaflumizone, or M.22B.1: 2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylene ]-N-[4-(difluoromethoxy)phenyl]-hydrazine amide or M.22B.2: N-(3-chloro-2-methylphenyl)-2-[(4- Chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazinamide; M.23 Inhibitors of acetyl CoA carboxylase, such as tetronic acid (Tetronic acid) and Tetramic acid derivatives, such as spirodiclofen, spiromesifen or spirotetramat; M.23.1 Spiropidion ; M.24 Mitochondrial complex IV electron transport inhibitors, for example M.24A Phosphines such as aluminum phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B Cyanides; M.25 Mitochondrial Electron transport inhibitors of complex II, such as β-ketonitrile derivatives, for example cyenopyrafen or cyflumetofen; M.28 Diamides of ryanodine Receptor modulators such as flubendiamide, chlorantraniliprole, cyantraniliprole, tetraniliprole, M.28.1: (R)- 3-chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2 -Methylsulfonylethyl)phthalamide, M.28.2: (S)-3-chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro- 1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamide, M.28.3: cyclobromide ( cyclaniliprole) or M.28.4: Methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl ]carbonyl}amino)benzoyl]-1,2-dimethylcarbazate; or M.28.5a) N-[4,6-dichloro-2-[(diethyl-λ-4 -thio)aminoformyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M.28.5b) N-[4-Chloro-2-[(diethyl-λ-4-sulfide)aminoformyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl) -5-(trifluoromethyl)pyrazole-3-carboxamide; M.28.5c) N-[4-chloro-2-[(di-2-propyl-λ-4-sulfide)amine Formyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M.28.5d) N -[4,6-Dichloro-2-[(di-2-propyl-λ-4-sulfide)aminoformyl]-phenyl]-2-(3-chloro-2-pyridyl) -5-(trifluoromethyl)pyrazole-3-carboxamide; M.28.5h) N-[4,6-dibromo-2-[(diethyl-λ-4-sulfide)amine Formyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M.28.5i) N-[2-( 5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1H -pyrazole-5-carboxamide; M.28.5j) 3-chloro-1-(3-chloro-2-pyridyl)-N-[2,4-dichloro-6-[[(1-cyano Base-1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide; M.28.5k) 3-bromo-N-[2,4-dichloro-6- (Methylcarbamoyl)phenyl]-1-(3,5-dichloro-2-pyridyl)-1H-pyrazole-5-carboxamide; M.28.5l) N-[4-chloro -2-[[(1,1-Dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridyl)-3-(fluoromethoxy )-1H-pyrazole-5-carboxamide; or M.28.6: cyhalodiamide; or M.29: cyhalodiamide - undetermined target site, e.g. Amines (flonicamid); M.UN. Insecticidal active compounds with unknown or unclear modes of action, such as afidopyropen, afoxolaner, azadirachtin, and amflumet (amidoflumet), benzoximate, broflanilide, bromopropylate, chinomethionat, cryolite, dicloromezotiaz, Dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, peralana (fluralaner), metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl, tioxazafen, M.UN.3: 11-(4-Chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11-ene-10 - Keto, M.UN.4: 3-(4'-Fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]decane -3-en-2-one, M.UN.5: 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl] -3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine, or an active agent based on bacillus firmus (Votivo, I-1582); M.UN.6 : Flupyrimin (flupyrimin); M.UN.8: Trifluzaindolizine; M.UN.9.a): 4-[5-(3,5-dichlorophenyl)-5 -(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide; M.UN .9.b): Fluxametamide; M.UN.10: 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy ]propoxy]-1H-pyrazole; M.UN.11.b) 3-(benzoylmethylamino)-N-[2-bromo-4-[1,2,2,3,3 ,3-Hexafluoro-1-(trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluoro-benzamide; M.UN.11.c) 3-( Benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(tri fluoromethyl)phenyl]-benzamide; M.UN.11.d) N-[3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-( Trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.11.e) N-[ 3-[[[2-bromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl ]-2-fluoro-phenyl]-4-fluoro-N-methyl-benzamide; M.UN.11.f) 4-fluoro-N-[2-fluoro-3-[[[2- Iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N- Methyl-benzamide; M.UN.11.g) 3-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1,2,2,2-tetrafluoro- 1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.11.h) 2-Chloro-N-[3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl) phenyl]amino]carbonyl]phenyl]-3-pyridinecarboxamide; M.UN.11.i) 4-cyano-N-[2-cyano-5-[[2,6-dibromo -4-[1,2,2,3,3,3-Hexafluoro-1-(trifluoromethyl)propyl]phenyl]aminoformyl]phenyl]-2-methyl-benzoyl Amine; M.UN.11.j) 4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4- [1,2,2,3,3,3-Hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide; M.UN.11.k) N- [5-[[2-Chloro-6-cyano-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl ]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.UN.11.l) N-[5-[[2-bromo-6-chloro-4 -[2,2,2-Trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2 -Methyl-benzamide; M.UN.11.m) N-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro- 1-(Trifluoromethyl)propyl]phenyl]aminoformyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.UN.11. n) 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethane yl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.11.o) 4-cyano-N-[2-cyano-5- [[2,6-Dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]aminoformyl]phenyl]-2-methyl -Benzamide; M.UN.11.p) N-[5-[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl ) ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; or M.UN.12.a) 2-(1 ,3-dioxan-2-yl)-6-[2-(3-pyridyl)-5-thiazolyl]-pyridine; M.UN.12.b) 2-[6-[2 -(5-fluoro-3-pyridyl)-5-thiazolyl]-2-pyridyl]-pyrimidine; M.UN.12.c) 2-[6-[2-(3-pyridyl)-5 -thiazolyl]-2-pyridyl]-pyrimidine; M.UN.12.d) N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridin-2- Formamide; M.UN.12.e) N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; M.UN.12 .f) N-ethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propionamide; M.UN.12.g) N -Methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propionamide; M.UN.12.h) N,2-di Methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propionamide; M.UN.12.i) N-ethyl-2 -Methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propionamide; M.UN.12.j) N-[4- Chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio-propionamide; M.UN.12.k) N-[4- Chloro-2-(3-pyridyl)thiazol-5-yl]-N,2-dimethyl-3-methylthio-propionamide; M.UN.12.l) N-[4-chloro- 2-(3-pyridyl)thiazol-5-yl]-N-methyl-3-methylthio-propionamide; M.UN.12.m) N-[4-chloro-2-(3- Pyridyl)thiazol-5-yl]-N-ethyl-3-methylthio-propionamide; M.UN.14a) 1-[(6-chloro-3-pyridyl)methyl]-1, 2,3,5,6,7-Hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine; or M.UN.14b) 1-[ (6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine-5 -alcohol; M.UN.16a) 1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.UN.16b) 1- (1,2-Dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16c) N,5- Dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1-methyl-ethyl)pyrazole-4-carboxamide; M.UN.16d) 1- [1-(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16e) N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16f) 1-(1,2-Dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16g) 1-[1 -(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16h) N-methyl -1-(2-fluoro-1-methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16i) 1-(4 ,4-difluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.UN.16j) 1-(4,4 -Difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide, M.UN.17a) N-(1-methylethyl)- 2-(3-pyridyl)-2H-indazole-4-carboxamide; M.UN.17b) N-cyclopropyl-2-(3-pyridyl)-2H-indazole-4-carboxamide Amine; M.UN.17c) N-cyclohexyl-2-(3-pyridyl)-2H-indazole-4-carboxamide; M.UN.17d) 2-(3-pyridyl)-N- (2,2,2-Trifluoroethyl)-2H-indazole-4-carboxamide; M.UN.17e) 2-(3-pyridyl)-N-[(tetrahydro-2-furyl )Methyl]-2H-indazol-5-carboxamide; M.UN.17f) Methyl 2-[[2-(3-pyridyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate ; M.UN.17g) N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridyl)-2H-indazole-5-carboxamide; M.UN.17h ) N-(2,2-difluoropropyl)-2-(3-pyridyl)-2H-indazole-5-carboxamide; M.UN.17i) 2-(3-pyridyl)-N -(2-pyrimidinylmethyl)-2H-indazole-5-carboxamide; M.UN.17j) N-[(5-methyl-2-pyrazinyl)methyl]-2-(3 -pyridyl)-2H-indazole-5-carboxamide, M.UN.18a) N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl- 3-(3,3,3-Trifluoropropylthio)propionamide; M.UN.18b) N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N -Ethyl-3-(3,3,3-trifluoropropylsulfinyl)propionamide; M.UN.18c) N-[3-chloro-1-(3-pyridyl)pyrazole- 4-yl]-3-[(2,2-difluorocyclopropyl)methylthio]-N-ethyl-acrylamide; M.UN.18d) N-[3-chloro-1-( 3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfinyl]-N-ethyl-acrylamide; M.UN.19Sa Lolaner (sarolaner), M.UN.20 Lotilaner (lotilaner); M.UN.21 N-[4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl] -1-Methyl-3-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide; M.UN.22a 2-(3-Ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, or M.UN.22b 2-[ 3-Ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine; M.UN .23a 4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl- 3-oxoisoxazolidine-4-yl]-2-methyl-benzamide, or M.UN.23b 4-[5-(3,5-dichloro-4-fluoro-phenyl )-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidine-4-yl]- 2-Methyl-benzamide; M.UN.24a) N-[4-chloro-3-(cyclopropylaminoformyl)phenyl]-2-methyl-5-(1,1, 2,2,2-Pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide or M.UN.24b) N-[4-chloro-3-[(1-cyano Cyclopropyl)aminoformyl]phenyl]-2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3- Formamide; M.UN.25 Ainuo Pai Rui (acynonapyr); M.UN.26 Benzpyrimoxan (benzpyrimoxan); M.UN.27 2-Chloro-N-(1-cyanocyclopropyl)- 5-[1-[2-Methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazol-3-yl]pyrazole-4- base] benzamide; M.29.28 oxazosulfyl (oxazosulfyl) (2-(3-ethylsulfonyl-2-pyridyl)-5-(trifluoromethylsulfonyl)-1,3 - benzoxazole); A) respiratory inhibitors - inhibitors of complex III of the Qo site: azoxystrobin (A.1.1), coumethoxystrobin (A.1.2), clove coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5), fenaminstrobin (A.1.6), Fenoxystrobin/flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), Mandalore Ice (mandestrobin) (A.1.10), fenoxystrobin (metominostrobin) (A.1.11), orysastrobin (orysastrobin) (A.1.12), picoxystrobin (picoxystrobin) (A.1.13), hundred Kemin (pyraclostrobin) (A.1.14), pyraclostrobin (pyrametostrobin) (A.1.15), pyraoxystrobin (pyraoxystrobin) (A.1.16), trifluorosensitive (trifloxystrobin) (A.1.17), 2 (2 -(3-(2,6-dichlorophenyl)-1-methyl-allylaminooxymethyl)-phenyl)-2 methoxyimino-N methyl-acetamide ( A.1.18), pyribencarb (A.1.19), triclopyricarb/chlorodincarb (A.1.20), famoxadone (A.1.21 ), Fenamidone (A.1.21), methyl-N-[2-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)oxymethyl]phenyl ]-N-methoxy-carbamate (A.1.22), 1-[3-chloro-2[[1(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl Base] phenyl] -4-methyl-tetrazol-5-one (A.1.23), 1-[3-bromo-2-[[1-(4-chlorophenyl) pyrazole-3-yl] Oxymethyl]phenyl]-4-methyl-tetrazol-5-one (A.1.24), 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxy Methyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one (A.1.25), 1-[2-[[1-(4-chlorophenyl)pyrazole- 3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one (A.1.26), 1-[2-[[1-(2,4-two Chlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one (A.1.27), 1-[3-cyclopropyl -2-[[2-Methyl-4 (1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4-methyl-tetrazol-5-one (A.1.30), 1 [3 (difluoromethoxy)-2-[[2-methyl-4-(1 methylpyrazol-3 base)phenoxy]methyl]phenyl]-4 methyl-tetrazole-5 - Ketone (A.1.31), 1-methyl-4-[3-methyl-2 [[2 methyl-4-(1-methylpyrazol-3 base) phenoxy] methyl] phenyl ]tetrazol-5-one (A.1.32), (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxyl-2-methoxyimine Base-N,3-dimethyl-pent-3-enamide (A.1.34), (Z,2E) 5 [1 (4-chlorophenyl) pyrazol-3-yl] oxy-2- Methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.35), pyriminostrobin (A.1.36), pyrflustrobin (bifujunzhi) (A.1.37 ), 2-(o-((2,5-dimethylphenyl-oxy-methylene)phenyl)-3-methoxy-methyl acrylate (A.1.38); Inhibitors of complex III: cyazofamid (A.2.1), amisulbrom (A.2.2), [(6S,7R,8R) 2-methylpropionic acid 8 benzyl Base-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-two-side oxy-1,5-two-side oxynonyl- 7-yl] esters (A.2.3), fenpicoxamid (A.2.4); - complex II inhibitors: benodanil (A.3.1), benzacrylfluconazole ( benzovindiflupyr) (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (fluopyram) (A.3.7), fudolanil (flutolanil) (A.3.8), fluoxapyroxad (fluxapyroxad) (A.3.9), Fulabi ( furametpyr (A.3.10), isofetamid (A.3.11), isopyrazam (A.3.12), mepronil (A.3.13), Carborough ( oxycarboxin) (A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16), pydiflumetofen (A.3.17), pyridoxine Pyraziflumid (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21), 3 (difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4 carboxamide (A.3.22), 3 (trifluoromethyl Base)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4 carboxamide (A.3.23), 1,3-dimethyl-N- (1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.24), 3-(trifluoromethyl)-1,5 dimethyl-N-( 1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.25), 1,3,5-trimethyl-N-(1,1,3-tri Methylindan-4-yl)pyrazole-4-carboxamide (A.3.26), 3-(difluoromethyl)-1,5 dimethyl-N-(1,1,3-trimethyl Indan-4-yl)pyrazole-4-carboxamide (A.3.27), 3-(difluoromethyl)-N(7-fluoro-1,1,3-trimethyl-indan-4 -yl)-1-methyl-pyrazole-4-carboxamide (A.3.28), N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl- 5-fluoro-1,3-dimethyl-pyrazole-4-carboxamide (A.3.29), (E)-2-[2-[(5-cyano-2-methyl-phenoxy ) methyl] phenyl] -3-methoxy-prop-2-enoic acid methyl ester (A.3.30), N-[(5-chloro-2-isopropyl-phenyl) methyl]-N- Cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide (A.3.31), 2-(difluoromethyl)-N-(1,1 , 3-trimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.32), 2-(difluoromethyl)-N-[(3R)-1,1,3-tri Methylindan-4-yl]pyridine-3-carboxamide (A.3.33), 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan- 4-yl)pyridine-3-carboxamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4 - Base] pyridine-3-carboxamide (A.3.35), 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine- 3-formamide (A.3.36), 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl]pyridine-3 -Formamide (A.3.37), 2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethyl-indan-4-yl)pyridine-3-formamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethyl-indan-4 base]pyridine-3-formamide ( A.3.39); - other respiratory inhibitors: diflumetorim (A.4.1); nitrophenyl derivatives: binapacryl (A.4.2), dinobuton (A. 4.3), dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone (A.4.7); Organometallic compounds: fentin salts, such as fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide ) (A.4.10); ametoctradin (A.4.11); silthiofam (A.4.12); B) Sterol biosynthesis inhibitors (SBI fungicides) - C14 to Methylase inhibitors: triazoles: azaconazole (B.1.1), bitertanol (B.1.2), bromuconazole (B.1.3), cyclogram ( cyproconazole) (B.1.4), difenoconazole (B.1.5), diniconazole (B.1.6), diniconazole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluquinazole (fluquinconazole) (B.1.10), flusilazole (B.1.11), flutriafol (B.1.11) .1.12), hexaconazole (B.1.13), imibenconazole (B.1.14), ipconazole (B.1.15), metconazole (B.1.17), Myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazole (B.1.20), penconazole (B.1.21), propiconazole ( B.1.22), prothioconazole (B.1.23), simeconazole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.1.26 ), triadimefon (B.1.27), triadimenol (B.1.28), triticonazole (B.1.29), uniconazole (B.1.30), Yifen Triconazole (ipfentrifluconazole) (B.1.37), mefentrifluconazole (B.1.38), 2-(chloromethyl)-2-methyl-5-(p-tolylmethyl)-1 (1,2,4-triazol-1-ylmethyl)cyclopentanol (B.1.43); imidazoles: imazalil (B.1.44), pefurazoate (B.1.45 ), prochloraz (B.1.46), triflumizol (B.1.47); pyrimidines, pyridines and piperazines: fenarimol (B.1.49), bifen Pyrifenox (B.1.50), triforine (B.1.51), [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenyl) Isoxazol-4-yl]-(3-pyridyl)methanol (B.1.52); - δ14-reductase inhibitors: adimorph (aldimorph) (B.2.1), mobendazim (dodemorph) (B .2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spiroxamine (B.2.8); - 3-keto reductase inhibitors: fenhexamid ( B.3.1); - Other sterol biosynthesis inhibitors: chlorphenomizole (B.4.1); C) Nucleic acid synthesis inhibitors - phenylamide or amido-amino acid fungicides: Benzolid benalaxyl (C.1.1), metalaxyl benalaxyl (benalaxyl-M) (C.1.2), fine benalaxyl (kiralaxyl) (C.1.3), metalaxyl (metalaxyl) (C.1.4 ), metalaxyl-M (C.1.5), ofurace (C.1.6), oxadixyl (C.1.7); Hymexazole (C.2.1), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5- Flucytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidine -4-amine (C.2.7), 5-fluoro-2(4-chlorophenylmethoxy)pyrimidin-4-amine (C.2.8); D) Inhibitors of cell division and cytoskeleton - tubulin inhibitors: immunity Benomyl (D.1.1), carbendazim (D.1.2), fuberidazole (D1.3), thiabendazole (D.1.4), thiophanate-methyl (thiophanate-methyl) (D.1.5), 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine (D.1.6), 3-chloro- 6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine (D.1.7), N ethyl-2-[(3-ethynyl-8-methyl- 6-quinolyl)oxy]butyramide (D.1.8), N-ethyl-2-[(3-ethynyl-8 methyl-6 quinolinyl)oxy]-2-methylthio Base-acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolin-yl)oxy]-N (2-fluoroethyl)butyramide (D. 1.10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methoxy-acetamide (D.1.11 ), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-propyl-butyramide (D.1.12), 2-[(3-ethynyl-8 -Methyl-6-quinolyl)oxy]-2-methoxy-N-propyl-acetamide (D.1.13), 2-[(3-ethynyl-8-methyl-6- Quinolinyl)oxy]-2-methylthio-N-propyl-acetamide (D.1.14), 2 [(3 ethynyl-8-methyl-6-quinolyl)oxy] -N-(2-fluoroethyl)-2-methylsulfanyl-acetamide (D.1.15), 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6 - fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine (D.1.16); - other cell division inhibitors: diethofencarb (D.2.1), ethaboxam ) (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone ( D.2.6), pyriofenone (D.2.7); E) amino acid and protein synthesis inhibitors - methionine synthesis inhibitors: cyprodinil (E.1.1), pyrimidine mepanipyrim (E.1.2), pyrimethanil (E.1.3); - protein synthesis inhibitors: blasticidin-S (blasticidin-S) (E.2.1), kasugamycin (kasugamycin) (E.2.2), kasugamycin hydrochloride hydrate (E.2.3), midiomycin (mildiomycin) (E.2.4), streptomycin (E.2.5), oxytetracycline (oxytetracyclin) (E.2.6); F) Signal transduction inhibitors - MAP/histidine kinase inhibitors: fluoroimid (F.1.1), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fludioxonil (F.1.5); - G protein inhibitors: quinoxyfen (F.2.1 ); G) Inhibitors of lipid and membrane synthesis - phospholipid biosynthesis inhibitors: edifenphos (G.1.1), propyl pine (iprobenfos) (G.1.2), pyrazophos (G. 1.3), isoprothiolane (G.1.4); - lipid peroxidation: dicloran (G.2.1), quintozene (G.2.2), tetrachloronitro Benzene (tecnazene) (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7); - Phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1), flumorph (G.3.2), mandipropamid (G.3.3 ), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate ( G.3.7); - Compounds affecting cell membrane permeability and fatty acids: propamocarb (G.4.1); - Inhibitors of oxidosterol-binding proteins: oxathiapiprolin (G.5.1), A Sulfonic acid 2-{3-[2-(1-{[3,5-bis(difluoromethyl-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3 -Thiazol-4-yl]-4,5-dihydro-1,2 oxazol-5-yl}phenyl ester (G.5.2), methanesulfonic acid 2-{3-[2-(1-{[3 ,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)1,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5 base}-3-chlorophenyl ester (G.5.3), 4-[1-[2-[3-(difluoromethyl)-5-methyl-pyrazol-1-yl ]acetyl]-4-piperidinyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.4), 4-[1-[2-[3,5-bis( Difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.5), 4-[1 -[2-[3-(Difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetralin-1-yl- Pyridine-2-carboxamide (G.5.6), 4-[1-[2-[5-cyclopropyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4- Piperidinyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.7), 4-[1-[2-[5-methyl-3-(trifluoromethyl)pyridine Azol-1-yl]acetyl]-4-piperidinyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.8), 4-[1-[2-[5 -(Difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetralin-1-yl-pyridine-2-formyl Amine (G.5.9), 4[1[2-[3,5-bis(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetralin-1 -yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl ]-4-piperidinyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.11); H) Inhibitor with multi-site action - Inorganic active substance: Bordeaux mixture (H .1.1), copper (H.1.2), copper acetate (H.1.3), copper hydroxide (H.1.4), basic copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7); - Thio- and dithiocarbamates: ferbam (H.2.1), zinc manganese (mancozeb) (H.2.2), manganese (maneb) ( H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H. 2.7), zineb (H.2.8), ziram (H.2.9); - organochlorine compounds: anilazine (H.3.1), chlorothalonil ) (H.3.2), captafol (H.3.3), captan (captan) (H.3.4), folpet (H.3.5), dichlofluanid (H. .3.6), dichlorophen (dichlorophen) (H.3.7), hexachlorobenzene (H.3.8), pentachlorophenol (H.3.9) and its salts, phthalide (phthalide) (H.3.10), methyl Yifaling (tolylfluanid) (H.3.11); - Guanidines and others: guanidine (H.4.1), dodine (H.4.2), donin free base (H.4.3), biguanide salt (guazatine) (H.4.4), biguanide salt acetate (H.4.5), kerejing (iminoctadine) (H.4.6), kerejing triacetate (H.4.7), gramrejing ginseng (alkane benzene sulfonate ) (H.4.8), dithianon (dithianon) (H.4.9), 2,6-dimethyl-1H,5H-[1,4]dithiano[2,3-c:5,6 -c'] dipyrrole-1,3,5,7(2H,6H)-tetraketone (H.4.10); I) cell wall synthesis inhibitor-dextran synthesis inhibitor: validamycin (validamycin) ( I.1.1), polyoxin B (I.1.2); - melanin synthesis inhibitors: pyroquilon (I.2.1), tricyclazole (I.2.2), Carpropamid (I.2.3), dicyclomet (I.2.4), fenoxanil (I.2.5); J) Plant protection inducers - acidified benzothiadiene Acibenzolar-S-methyl (acibenzolar-S-methyl) (J.1.1), probenazole (J.1.2), isotianil (J.1.3), tiadinil ( J.1.4), prohexadione-calcium (J.1.5); phosphonates: fosetyl (J.1.6), fosetyl-aluminum (J.1.7), Phosphorous acid and its salts (J.1.8), calcium phosphonate (J.1.11), potassium phosphonate (J.1.12), potassium or sodium bicarbonate (J.1.9), 4 cyclopropyl-N-( 2,4-Dimethoxyphenyl)thiadiazole-5-carboxamide (J.1.10); K) Mode of action unknown - bronopol (K.1.1), chinomethionat (K.1.2), cyflufenamid (K.1.3), cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K. 1.6), Diclocymet (K.1.7), Diclomezine (K.1.8), Difenzoquat (K.1.9), Difenzoquat methyl sulfate (K. 1.10), diphenylamine (K.1.11), fenitropan (K.1.12), fenpyrazamine (K.1.13), flumetover (K. 1.14), Flusulfamide (K.1.15), Flutianil (K.1.16), Harpin (K.1.17), Metha-sulfocarb (K. 1.18), nitrapyrin (K.1.19), nitrothal-isopropyl (K.1.20), tolprocarb (K.1.21), oxin-copper ( K.1.22), Proquinazid (K.1.23), Tebufloquin (K.1.24), Tecloftalam (K.1.25), Triazoxide ( K.1.26), N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methylformamidine (K.1.27), N'(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methylmethanol Amidine (K.1.28), N'-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5 -Dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1.29), N'-(5-bromo-6-indan-2-yloxy-2-methyl -3-pyridyl)-N-ethyl-N-methyl-formamidine (K.1.30), N'-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy Base]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.31), N'-[5-bromo-6-(4-isopropylcyclohexane Oxygen)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.32), N'[5 bromo-2-methyl-6-(1-benzene Ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.33), N'-(2-methyl-5-trifluoromethyl-4-(3 -Trimethylsilyl-propoxy)-phenyl)-N-ethyl-N-methylformamidine (K.1.34), N'-(5-difluoromethyl-2 methyl-4- (3-trimethylsilyl-propoxy)-phenyl)-N-ethyl-N-methylformamidine (K.1.35), 2-(4-chloro-phenyl)-N-[4 -(3,4-dimethoxy-phenyl)-isoxazol-5 base]-2-prop-2-ynyloxy-acetamide (K.1.36), 3 [5-(4-chloro -phenyl)-2,3-dimethyl-isoxazolidine-3-yl]-pyridine (pyrisoxazole (pyrisoxazole)) (K.1.37), 3-[5-(4-methylbenzene Base)-2,3-dimethyl-isoxazolidine-3 base]-pyridine (K.1.38), 5-chloro-1 (4,6-dimethoxy-pyrimidin-2-yl)-2 -Methyl-1H-benzimidazole (K.1.39), (Z) 3 amino-2-cyano-3-phenyl-prop-2-enoic acid ethyl ester (K.1.40), picabucil ( picarbutrazox) (K.1.41), N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2 -pyridyl]amyl carbamate (K.1.42), N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino] Oxymethyl]-2-pyridyl]but-3-ynyl carbamate (K.1.43), 2-[2-[(7,8-difluoro-2-methyl-3-quinoline Base) oxy]-6-fluoro-phenyl]propan-2-ol (K.1.44), 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl) Oxy]phenyl]propan-2-ol (K.1.45), quinofumelin (K.1.47), 9-fluoro-2,2-dimethyl-5-(3-quinolinyl )-3H 1,4 benzoxazepine (K.1.49), 2-(6-benzyl-2-pyridyl)quinazoline (K.1.50), 2-[6-(3-fluoro- 4 methoxy-phenyl)-5-methyl-2-pyridyl]quinazoline (K.1.51), dichlorobenzenethia (dichlobentiazox) (K.1.52), N'-(2,5-di Methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine (K.1.53); dipymetitrone (dipymetitrone), isoflurane (isoflucypram); Fluinda Fluindapyr, inpyrfluxam, pyrifenamine.

Commercially available compounds of Group M listed above can be found in The Pesticide Manual, 17th Edition, C. MacBean, British Crop Protection Council (2015) and other publications. The online Pesticide Manual is regularly updated and can be accessed at http://bcpcdata.com/pesticide-manual.html.

Another online database of pesticides that provides ISO common names is http://www.alanwood.net/pesticides.

M.4 Cyclopyrid is known from WO2010/069266 and WO2011/069456. M.4A.1 is known from CN 103814937; CN105367557, CN 105481839. M.4A.2 guadipyr is known from WO 2013/003977 and M.4A.3 (approved in China as paichongding) is known from WO 2007/101369. M.22B.1 is described in CN10171577 and M.22B.2 is described in CN102126994. Spiperone M.23.1 is known from WO 2014/191271. M.28.1 and M.28.2 are known from WO2007/101540. M.28.3 is described in WO2005/077934. M.28.4 is described in WO2007/043677. M.28.5a) to M.28.5d) and M.28.5h) are described in WO 2007/006670, WO 2013/024009 and WO 2013/024010, M.28.5i) in WO 2011/085575, M.28.5j ) is described in WO2008/134969, M.28.5k) in US2011/046186 and M.28.5l) in WO2012/034403. M.28.6 can be found in WO2012/034472. M.UN.3 is known from WO2006/089633 and M.UN.4 is known from WO2008/067911. M.UN.5 is described in WO2006/043635 and Bacillus firmus based biocontrol agents are described in WO2009/124707. Fluoropyrazines are described in WO2012/029672. M.UN.8 is known from WO2013/055584. M.UN.9.a) is described in WO2013/050317. M.UN.9.b) is described in WO2014/126208. M.UN.10 is known from WO2010/060379. Bromfluflubenil and M.UN.11.b) to M.UN.11.h) are described in WO2010/018714, and M.UN.11i) to M.UN.11.p) are described in in WO 2010/127926. M.UN.12.a) to M.UN.12.c) are known from WO2010/006713, M.UN.12.d) and M.UN.12.e) are known from WO2012/000896, and M .UN.12.f) to M.UN.12.m) are known from WO 2010/129497. M.UN.14a) and M.UN.14b) are known from WO 2007/101369. M.UN.16.a) to M.UN.16h) are described in WO2010/034737, WO2012/084670 and WO2012/143317 respectively, and M.UN.16i) and M.UN.16j) are described in WO2015/055497 middle. M.UN.17a) to M.UN.17.j) are described in WO2015/038503. M.UN.18a) to M.UN.18d) are described in US2014/0213448. M.UN.19 is described in WO2014/036056. M.UN.20 is known from WO2014/090918. M.UN.21 is known from EP2910126. M.UN.22a and M.UN.22b are known from WO2015/059039 and WO2015/190316. M.UN.23a and M.UN.23b are known from WO2013/050302. M.UN.24a and M.UN.24b are known from WO2012/126766. Enopariet M.UN.25 is known from WO 2011/105506. Benzpimoram M.UN.26 is known from WO2016/104516. M.UN.27 is known from WO2016174049. Compound M.29.28 is known from WO2017104592.

Fungicides described by IUPAC nomenclature, their preparation and their pesticidal activity are also known (see Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 141 317; -A 152 031; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941; -A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; US 3,296,272; US 3,325,503; WO 98/46608; 7; WO 99/24413; WO 99/27783 WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501; WO 01/56358; WO 02/22583; WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491; WO 04/49804; WO 05/63721; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; , WO2012/168188, WO 2007/006670, WO 2011/77514; WO13/047749, WO 10/069882, WO 13/047441, WO 03/16303, WO 09/90181, WO 13/007767, WO 13/010862 , WO 13/127704, WO 13/024009, WO 13/024010 and WO 13/047441, WO 13/162072, WO 13/092224, WO 11/135833), CN 1907024, CN 1456054, CN 103387541, CN 1309 897, WO 12/ 84812, CN 1907024, WO 09094442, WO 14/60177, WO 13/116251, WO 08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO 07/129454, WO 12/165511, WO 1 1/081174 , WO 13/47441).

In another embodiment, the invention relates to a mixture comprising a compound of formula (I) as described above, especially compound I-1 or I-R-1, and at least one compound II, which compound II is metaldehyde, especially in granular form metaldehyde.

In another embodiment, the present invention relates to a compound comprising formula (I) as described above, especially compound I-1 or I-R-1 and at least one compound selected from the group consisting of methiadinil, anthraquinone, β-amine A mixture of compound II of the group of butyric acid, laminarin, polyglucosamine, thiamine and riboflavin.

In another embodiment, the invention relates to a method according to the invention, the administration of which comprises a compound of formula (I) as described above, especially compound I-1 or I-R-1 and at least one selected from the group consisting of hydroxyadenine (also Compound II of the group known as zeatin), actin (hydroxylene) adenine, brassinolide, insecticidal extract of Celastrus angulatus, matrine, osthole, tetracycline .

In another embodiment, the invention relates to compounds comprising a non-racemic compound of formula (I) as described above, especially compound I-1 with an enantiomeric excess of compound I-R-1 and at least one compound II Mixture, the compound II is metaldehyde, especially granular metaldehyde.

In another embodiment, the invention relates to a compound I-1 comprising a non-racemic compound of formula (I) as described above, especially compound I-1 having an enantiomeric excess of compound I-R-1, and at least one selected from A mixture of compound II from the group of thiamin, anthraquinone, β-aminobutyric acid, laminarose, polyglucosamine, thiamine and riboflavin.

In another embodiment, the invention relates to a method according to the invention for administering a non-racemic compound comprising formula (I) as described above, especially compound I with enantiomeric excess of compound I-R-1 - 1 and at least one selected from the group consisting of hydroxyalkene adenine (also known as zeatin), actin (hydroxyalkene) adenine, brassinolide, insecticidal extract of Phyllostachys chinensis, matrine, osthole . A mixture of compounds II of the group of tetracyclines.

The invention relates to at least one compound I according to the invention or a non-racemic compound of formula (I) or a compound of formula (I) having an enantiomeric excess of a compound of formula (I-R) or (I-S) as component I and A mixture of at least one mixing partner II as defined above. In one embodiment, the invention relates to a binary mixture of a component I and a mixing partner II as defined above as component II.

The preferred weight ratio of such binary mixtures is from 10000:1 to 1:10000, preferably from 7000:1 to 1:7000, also preferably from 5000:1 to 1:5000, also preferably from 1000:1 to 1:1000 , more preferably 100:1 to 1:100, more preferably 70:1 to 1:70, especially preferably 25:1 to 1:25, and especially preferably 10:1 to 1:10. In such binary mixtures, components I and II may be used in equal amounts, or an excess of either component I or component II may be used.

In the mixtures according to the invention, the ingredients can be used sequentially or in combination with one another and, if appropriate, only added immediately before use (tank mixing). By way of example, plants can be sprayed with compound II before or after treatment with component I.

In one embodiment of the present invention, the mixture of the present invention is a compound of formula (I), preferably (I-R), preferably compound I-1, I-R-1, I-2 or I-R-2 and a group selected from the following Mixtures of compounds: Mianlaide, Befenti, Epreza, Fluquinazole, Hutifene, Husilide, Meteza, Amidamide, Prothioconazole, Decrell, Fenconazole, Becamine , Trifluramine, Bai Kelie, Damifen, Penthiopyrad, Mobendazim, Fembuton, Fenpro, Propoxyquinoline, Pyrimethanil, Sandofen, Manganap, Zincmanganate Pu, avoid rotten, deendi, tetrachloroisobenzonitrile, cyanothioquinone, fluthiazide, mefenon, flucloxacin, mustzaphen, penfufen, fluxachlor, pyraclostrobin , Oxazoxafil. Especially preferred are becamine, oxazoxafil, and flufenadim.

In one embodiment of the present invention, the mixture of the present invention is a compound of formula (I), preferably (I-R), preferably compound I-1, I-R-1, I-2 or I-R-2 and a group selected from the following Mixture of compounds: imidacloprid, clothianidin, dinotefuran, chlorantraniliprole, cyantraniliprole, spinosad, spinosad, ethiprole, fipronil, trifluridine, fluridine Pyridamide, oxazoxafil, and cyantraniliprole.

In one embodiment of the present invention, the mixture of the present invention is a compound of formula (I), preferably (I-R), preferably compound I-1, I-R-1, I-2 or I-R-2 and a group selected from the following Mixtures of compounds: phytopyrene, isotianil, tricypyrazole, bacquilone, rice blastin, toproca, gapamide, dicloximol, yatormin, oxazoxafil, and oxime ether Bacteramine.

In one embodiment of the present invention, the mixture of the present invention is a compound of formula (I), preferably (I-R), preferably compound I-1, I-R-1, I-2 or I-R-2 and a group selected from the following Mixture of compounds: Forabi, cyflufen, silfluazole, penfofen, ytropamine, orysastrobin.

In one embodiment of the present invention, the mixture of the present invention is a compound of formula (I), preferably (I-R), preferably compound I-1, I-R-1, I-2 or I-R-2 and oxazoxafil mixture.

In one embodiment of the invention, the mixture of the invention is a non-racemic compound of formula (I), preferably a compound of formula (I) with enantiomeric excess compound (I-R), preferably with enantiomeric Compound I-1 of isomer excess compound I-R-1, or a compound of formula (I-R), preferably a mixture of compound I-R-1 and a compound selected from the following group: M.2: GABA-gated chloride channel antagonist ; M.3: Sodium channel modulator; M.4: Nicotinic acetylcholine receptor agonist; M.5: Nicotinic acetylcholine receptor ectopic activator; M.6: Avermella M.9: TRPV channel modulator of chitins and milbemycins; M.13: Decoupler of oxidative phosphorylation via disruption of proton gradient; M.15: Chitin biosynthesis Type 0 inhibitors; M.16: Chitin biosynthesis type inhibitors; M.22: Voltage-dependent sodium channel blockers; M.23: Acetyl CoA carboxylase inhibitors; M.28: Rianodine receptor modulators of diamides; M.29: Chord modulators; M.UN.9.b; M.29.28; Respiratory inhibitors: inhibitors of complex III of the Qo site, Inhibitors of complex III at the Qi site, inhibitors of complex II; sterol biosynthesis inhibitors; lipid and membrane synthesis inhibitors; cell wall synthesis inhibitors, preferably melanin synthesis inhibitors; plant protection inducers; II Closimo (K.1.7); Topoloca (K.1.21) and Picabusi (K.1.41).

In one embodiment of the invention, the mixture of the invention is a non-racemic compound of formula (I), preferably a compound of formula (I) with enantiomeric excess compound (I-R), preferably with enantiomeric Compound I-1 of isomer excess compound I-R-1, or a compound of formula (I-R), preferably a mixture of compound I-R-1 and a compound selected from the following group: fipronil, α-samethonine, Kefan Pie, metaflumizone, abatine, permetrazine, thiamethoxam, imidacloprid, dinotefuran, dinotefuran, clothianidin, sulfonicamid, spirotetramat, bufenjing, chlorantraniliprole Benzamide, cyantraniliprole, flucytraniliprole, sulfoxaflor, Indec, triflumezil, ethiproleil, cinot, ciproxil, spiropedone, fluzolid Ammonium, Penfufen, Trisacetazole, Yatropin, Daobenling, Toproca, Gapramine, Dicloximo, Forabi, Silfluazole, Phthalox, Oryzastrobin, Perquick Long, Seflumet, Pikabuxi, Oxazoxafil, Mefenox, Flubendiamide, Flufenuron, Sazamet, Metalaxyl, Indazole Sulfamide, Cyclotranil, Diphenhydramine Chloramethanil and Isotianil. Especially preferred are α-sermetazim, flunicamid, fluazolamide, cinot, Indec, oxazoxafil, permetazine, triflumezine, flufenon, and frabic , metalaxyl, culmex, diclofenac, penfofen, baclavon, silfluzole, ibufengin, trixazole, or spinosad.

In one embodiment of the invention, the mixture of the invention is a non-racemic compound of formula (I), preferably a compound of formula (I) with enantiomeric excess compound (I-R), preferably with enantiomeric Compound I-1 of isomer excess compound I-R-1, or a compound of formula (I-R), preferably a mixture of compound I-R-1 and a compound selected from the following group: fipronil, α-samethonine, Kefan Pie, metaflumizone, abatine, permetrazine, thiamethoxam, imidacloprid, dinotefuran, dinotefuran, clothianidin, sulfonicamid, spirotetramat, bufenjing, chlorantraniliprole Benzamide, cyantraniliprole, flucytraniliprole, sulfoxaflor, Indec, triflumezil, ethiproleil, cinot, ciproxil, spiropedone, fluzolid amines, oxazoxafil, mefenol, flubendiamide, flufenoron, and cyclobromide.

In one embodiment of the invention, the mixture of the invention is a non-racemic compound of formula (I), preferably a compound of formula (I) with enantiomeric excess compound (I-R), preferably with enantiomeric Compound I-1 of compound I-R-1 with excess isomers, or compound of formula (I-R), preferably compound I-R-1 and a mixture of compounds selected from the following group: phalloxer, trixazole, bactimer, rice Plague, Toproca, Gapromide, Diclosimo, Yatropamine, Oryzastrobin, Forabi, Seflumet, Silfluzole, Penfufen, Picabuxi, Cyzamil, Metalaxyl, Indazolesulfin, and Isotianil.

In one embodiment of the invention, the mixture of the invention is a non-racemic compound of formula (I), preferably a compound of formula (I) with enantiomeric excess compound (I-R), preferably with enantiomeric A mixture of compound I-1 of compound I-R-1 with isomer excess and a compound selected from the group consisting of: fipronil, α-samethenin, kefanpai, metaflumizone, abatine, permetazine , thiamethoxam, imidacloprid, dinotefuran, dinotefuran, clothianidin, chlorantraniliprole, spirotetramat, buffungin, chlorantraniliprole, cyantraniliprole, flucytraniliprole Amine, sulfoxaflor, Indec, trifluoropyrimidine, ethipromin, spinoxal, spinosad, spiropedone, flufenamide, penfufen, trisethazole, yatormin, Dablasin, Toproca, Gapromide, Diclosimo, Forabi, Sifluzole, Phthalox, Oryzastrobin, Bacquilone, Seflumet, Picabuxi, Oxazoxafil , Mefenox, Flubendiamide, Flufenuron, Cyclomethan, Metalaxyl, Indazolesulphamide, Cyclotranil, Diclofenamide and Isotianil. Especially preferred are α-sermetazim, flunicamid, fluazolamide, cinot, Indec, oxazoxafil, permetazine, triflumezine, flufenon, and frabic , metalaxyl, culmex, diclofenac, penfofen, baclavon, silfluzole, ibufengin, trixazole, or spinosad.

In one embodiment of the invention, the mixture of the invention is a non-racemic compound of formula (I), preferably a compound of formula (I) with enantiomeric excess compound (I-R), preferably with enantiomeric A mixture of compound I-1 of compound I-R-1 with isomer excess and a compound selected from the group consisting of: fipronil, α-samethenin, kefanpai, metaflumizone, abatine, permetazine , thiamethoxam, imidacloprid, dinotefuran, dinotefuran, clothianidin, chlorantraniliprole, spirotetramat, buffungin, chlorantraniliprole, cyantraniliprole, flucytraniliprole Amine, sulfoxaflor, Indec, triflumepyrim, ethiprole, spinoxate, spinoxal, spiropedone, fluazolamide, oxazoxafil, mefenox, sulfluramid Fenamide, Flufenuron, and Cyclotranil.

In one embodiment of the invention, the mixture of the invention is a non-racemic compound of formula (I), preferably a compound of formula (I) with enantiomeric excess compound (I-R), preferably with enantiomeric The mixture of the compound I-1 of the isomer excess compound I-R-1 and the compound selected from the following group: phylloxal, trixazole, bacquiron, rice blastin, toproca, gapamide, dichloro Simox, Yatropin, Oryzastrobin, Forabi, Sefluprom, Silfluzol, Penfofen, Pikabuxi, Cyzam, Metalaxyl, Indazolesulfazan, and Isotianil .

In one embodiment of the present invention, the mixture of the present invention is a mixture of a non-racemic compound of formula (I), preferably a compound of formula (I-R), preferably compound I-R-1 and a compound selected from the following group: Fipronil, α-Semetenin, Kefanpai, Metaflumizone, Abatine, Permetazine, Thiamethoxam, Imidacloprid, Dinotefuran, Dinotefuran, Clothianidin, Sulfacamid , spirotetramat, ibufenjing, chlorantraniliprole, cyantraniliprole, flucytraniliprole, sulfoxaflor, Indec, trifluoropyrim, ethifen, cinot , Spinosad, Spirophenone, Fluazolamide, Penfufen, Trisazole, Yatropin, Daofengling, Toproca, Gapromide, Diclosimo, Forabi, Silicon Fluoride azoles, culpy fever, oryzastrobin, bacquilone, seflumet, picabusil, oxazoxafil, mefenol, flubendiamide, flufenon, cyzamet, metalaxyl, indole Fensulfam, Cyclotranil, Diclofen, and Isotianil. Especially preferred are α-sermetazim, flunicamid, fluazolamide, cinot, Indec, oxazoxafil, permetazine, triflumezine, flufenon, and frabic , metalaxyl, culmex, diclofenac, penfofen, baclavon, silfluzole, ibufengin, trixazole, or spinosad.

In one embodiment of the present invention, the mixture of the present invention is a mixture of a non-racemic compound of formula (I), preferably a compound of formula (I-R), preferably compound I-R-1 and a compound selected from the following group: Fipronil, α-Semetenin, Kefanpai, Metaflumizone, Abatine, Permetazine, Thiamethoxam, Imidacloprid, Dinotefuran, Dinotefuran, Clothianidin, Sulfacamid , spirotetramat, ibufenjing, chlorantraniliprole, cyantraniliprole, flucytraniliprole, sulfoxaflor, Indec, trifluoropyrim, ethifen, cinot .

In one embodiment of the present invention, the mixture of the present invention is a mixture of a non-racemic compound of formula (I), preferably a compound of formula (I-R), preferably compound I-R-1 and a compound selected from the following group: Culling fever, Trisacetazole, Bacquilon, Daobenling, Topuroca, Gaprimide, Diclosimo, Yatropin, Oryzastrobin, Forabi, Seflumet, Silfluazole, Penfufen, Pikabuxi, Cyzamil, Metalaxyl, Indazolesulfin and Isotianil.

In one embodiment of the present invention, the mixture of the present invention is a non-racemic compound of formula (I), preferably a compound of formula (I), preferably compound I- with enantiomeric excess compound I-R-1 1 Mixture with a compound selected from the following group: α-Sermetazine, Fluoxetamid, Fluoxenamide, Sinoxate, Indec, Oxazoxafil, Permethazine, Trifluridine , fenflurone, fulabic, metalaxyl, thuloxal, diclofenac, penfofen, baccaron, silfluzole, ibufengin, trixazole, or spinosad.

In one embodiment of the present invention, the mixture of the present invention is a mixture of a non-racemic compound of formula (I), preferably a compound of formula (I-R), preferably compound I-R-1 and a compound selected from the following group: α-Samilin, Fluoxetamid, Fluazolamide, Cinot, Indec, Oxazoxafil, Permetazine, Trifluridine, Flufenuron, Forabi, Metalaxyl , culling fever, diclofenac, penfufen, baclavon, silfluzole, ibufengin, trixazole, or spinosad.

In one embodiment of the present invention, the mixture of the present invention is a non-racemic compound of formula (I), preferably a compound of formula (I), preferably compound I- with enantiomeric excess compound I-R-1 1 or a mixture of 1-2 and oxazoxafil having an enantiomeric excess of compound I-R-2.

Particularly preferred mixtures according to the invention are listed in Table M below, wherein compound I is as defined in the specification: Table M

Analogously to mixtures M-1 to M-138, mixtures of non-racemic compound 1-1 instead of compound 1-1 are part of the present invention.

Similar to mixtures M-1 to M-138, mixtures in which I-2 replaces I-1 are part of the invention.

Similar to mixtures M-139 to M-276, mixtures in which I-R-2 replaces I-R-1 are part of this invention.

Similar to mixtures M-1 to M-138, mixtures in which I-3 replaces I-1 are part of the invention.

Similar to mixtures M-139 to M-276, mixtures in which I-R-3 replaces I-R-1 are part of this invention.

Similar to mixtures M-1 to M-138, mixtures in which I-4 replaces I-1 are part of the invention.

Similar to mixtures M-139 to M-276, mixtures in which I-R-4 replaces I-R-1 are part of this invention.

Similar to mixtures M-1 to M-138, mixtures in which I-5 replaces I-1 are part of the invention.

Similar to mixtures M-139 to M-276, mixtures in which I-R-5 replaces I-R-1 are part of this invention.

Similar to mixtures M-1 to M-138, mixtures in which I-6 replaces I-1 are part of the invention.

Similar to mixtures M-139 to M-276, mixtures in which I-R-6 replaces I-R-1 are part of this invention.

Similar to mixtures M-1 to M-138, mixtures having I-1 of compound I-R-1 in enantiomeric excess instead of I-1 are part of the present invention.

extra mix The mixtures according to the invention may be combined and mixed with other active ingredients for application in agriculture, for example with other pesticides, insecticides, nematicides, fungicides, herbicides, safeners, fertilizers such as ammonium nitrate, urea, potash and superphosphate), phytotoxicants and plant growth regulators.

Such mixtures are also covered by the term "mixtures according to the invention" or "mixtures according to the invention".

These additional ingredients can be used sequentially or in combination with the mixtures according to the invention and, if appropriate, only added immediately before use (tank mixing). By way of example, plants can be sprayed with the mixtures according to the invention either before or after treatment with the other active ingredients.

Mixing partners are optionally suicide pests, especially insecticides, nematicides and acaricides, fungicides, herbicides, plant growth regulators, fertilizers and the like. Preferred mixing partners are insecticides, nematicides and fungicides.

In one embodiment, the invention relates to a ternary mixture comprising compound I, compound II and another compound III which is different from compound I or II already present in the mixture.

In a sub-embodiment, the invention relates to a mixture of: (1) Compound of formula (I), or non-racemic compound of formula (I) or compound of formula (I) or compound (I-R) with enantiomeric excess (I-R), preferably non-racemic compound I-1 or compound I-1 or compound I-R-1 or I-2 or I-R-2 with enantiomeric excess I-R-1, and (2) Compounds selected from the following group: imidacloprid, clothianidin, dinotefuran, chlorantraniliprole, cyantraniliprole, spinosad, spinosad, ethiprole, fipronil, fluoropyrim, flunicamid, oxazoxafil, and flucynamid, and (3) Compounds selected from the following group: phytopyrene, isotianil, trisacilazole, bacquilon, rice blastin, toproca, gapromide, dicloximol, yatormine, oxime Kyssastrobin.

In one embodiment, the invention relates to a 4-way mixture comprising compound I, compound II and two additional compounds III, different from compound I or II already present in the mixture.

In a sub-embodiment, the invention relates to a mixture of: (1) Compound of formula (I), or non-racemic compound of formula (I) or compound of formula (I) or compound (I-R) with enantiomeric excess (I-R), preferably non-racemic compound I-1 or compound I-1 or compound I-R-1 or I-2 or I-R-2 with enantiomeric excess I-R-1, and (2) Compounds selected from the following group: imidacloprid, clothianidin, dinotefuran, chlorantraniliprole, cyantraniliprole, spinosad, spinosad, ethiprole, fipronil, fluoropyrim, flunicamid, oxazoxafil, and flucynamid, and (3) Compounds selected from the following group: phytopyrene, isotianil, trisacilazole, bacquilon, rice blastin, toproca, gapromide, dicloximol, yatormine, oxime kysastrobin, and (4) A compound selected from the following group: Forabi, Salfluramine, Silfluzole, Penfofen, Yatropamine, oryzastrobin, provided that it is different from the compound in (3).

In one embodiment, the invention relates to a 5-way mixture comprising Compound I, Compound II and three additional Compounds III which are different from Compound I or II already present in the mixture.

formulation The invention also relates to agrochemical compositions comprising an adjuvant and at least one compound according to the invention or a mixture thereof.

Agrochemical compositions comprise a pesticidally effective amount of a compound of the invention or a mixture thereof. The term "pesticidally effective amount" is defined below.

The compounds of the invention or mixtures thereof can be converted into agrochemical compositions of the customary type, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, compressed formulations, capsules and mixtures thereof. Examples of composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, tablets formulations, wettable powders (eg WP, SP, WS, DP, DS), compressed formulations (eg BR, TB, DT), granules (eg WG, SG, GR, FG, GG, MG), insecticidal preparations ( eg LN) and gel formulations for the treatment of plant propagation material such as seeds (eg GF). These and other composition types are defined in "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th Edition. May 2008, CropLife International.

Compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

Examples of suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners Agents, moisturizers, protective agents, attractants, feeding stimulants, extenders, bactericides, antifreeze agents, defoamers, colorants, thickeners and adhesives.

Suitable solvents and liquid carriers are water and organic solvents, such as medium to high boiling mineral oil fractions, for example kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, for example toluene, paraffin, Tetrahydronaphthalene, alkylated naphthalene; alcohols such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; diols; DMSO; ketones such as cyclohexanone; esters such as lactate, carbonate, fatty acids esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides such as N-methylpyrrolidone, fatty acid dimethylamide; and mixtures thereof.

Suitable solid carriers or fillers are mineral earths, such as silicate, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powder , such as cellulose, starch; fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; products of plant origin, such as cereal flour, bark flour, wood flour, nut shell flour and mixtures thereof.

Suitable surfactants are surface-active compounds such as anionic, cationic, nonionic and amphoteric surfactants; block polymers, polyelectrolytes and mixtures thereof. Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids or adjuvants. Examples of surfactants are listed in McCutcheon's Volume 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International or North American version).

Suitable anionic surfactants are alkali metal, alkaline earth metal or ammonium salts of sulfonates, sulfates, phosphates, carboxylates and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefinsulfonates, lignosulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols Acid salts, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalene, sulfonates of dodecyl and tridecylbenzene, sulfonates of naphthalene and alkylnaphthalene, sulfosuccinate salt or sulfosuccinamate. Examples of sulfates are the sulfates of fatty acids and oils, ethoxylated alkylphenols, alcohols, ethoxylated alcohols or fatty acid esters. Examples of phosphoric acid esters are phosphoric acid esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohol or alkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds which have been alkoxylated with 1 to 50 equivalents, such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters. The alkoxylation can be carried out with ethylene oxide and/or propylene oxide, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucosamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerides or monoglycerides. Examples of sugar-based surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinylpyrrolidone, vinyl alcohol or vinyl acetate.

Suitable cationic surfactants are quaternary surfactants, such as quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are A-B or A-B-A type block polymers comprising polyethylene oxide and polypropylene oxide blocks, or A-B-C type block comprising alkanol, polyethylene oxide and polypropylene oxide blocks polymer. Suitable polyelectrolytes are polyacids or bases. Examples of polyacids are alkali metal salts of polyacrylic acid or polyacid comb polymers. Examples of polybasic bases are polyvinylamine or polyethyleneamine.

Suitable adjuvants are compounds which themselves have negligible or even no pesticidal activity and which improve the biological efficacy of the compounds according to the invention on the target. Examples are surfactants, mineral or vegetable oils and other auxiliaries. Other examples are given by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, Chapter 5.

Suitable thickeners are polysaccharides (eg Sanxian gum, carboxymethylcellulose), non-organic clays (organically modified or not), polycarboxylates and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazolinones.

Suitable antifreezes are ethylene glycol, propylene glycol, urea and glycerin.

Suitable defoamers are silicones, long-chain alcohols and fatty acid salts.

Suitable colorants, eg red, blue or green, are low water soluble pigments and water soluble dyes. Examples are inorganic colorants such as iron oxide, titanium oxide, ferric hexacyanoferrate and organic colorants such as alizarin, azocyanine and phthalocyanine colorants.

Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biological or synthetic waxes and cellulose ethers.

Examples of composition types and their preparation are: i) Water-soluble concentrates (SL, LS) 10-60% by weight of compounds I or II or mixtures according to the invention and 5-15% by weight of wetting agents (e.g. alcohol alkoxylates) are dissolved in water and/or water-soluble solvents (e.g. alcohols) up to 100% by weight . The active substance dissolves on dilution with water. ii) Dispersible Concentrate (DC) 5-25% by weight of compounds I or II or mixtures according to the invention and 1-10% by weight of dispersants (eg polyvinylpyrrolidone) are dissolved in up to 100% by weight of organic solvents (eg cyclohexanone). Dilute with water to obtain a dispersion. iii) Emulsifiable Concentrate (EC) 15-70% by weight of compounds I or II or mixtures according to the invention and 5-10% by weight of emulsifiers (such as calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in up to 100% by weight of water-insoluble in organic solvents such as aromatic hydrocarbons. Dilute with water to give an emulsion. iv) Emulsions (EW, EO, ES) Dissolve 5-40% by weight of compound I or II or mixtures according to the invention and 1-10% by weight of emulsifiers (such as calcium dodecylbenzenesulfonate and castor oil ethoxylate) in 20-40% by weight of water in insoluble organic solvents such as aromatic hydrocarbons. This mixture is introduced into up to 100% by weight of water by means of an emulsifier and a homogeneous emulsion is produced. Dilute with water to give an emulsion. v) Suspensions (SC, OD, FS) In an agitating ball mill, 20-60% by weight of compounds I or II or mixtures according to the invention are pulverized, 2-10% by weight of dispersants and wetting agents (such as sodium lignosulfonate and alcohol ethoxylates) are added, 0,1-2% by weight thickener (such as Sanxian gum) and up to 100% by weight water, resulting in a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS-type compositions, up to 40% by weight of binder (eg polyvinyl alcohol) is added. vi) Water-dispersible granules and water-soluble granules (WG, SG) 50-80% by weight of compounds I or II or mixtures according to the invention are finely ground, up to 100% by weight of dispersants and wetting agents (such as sodium lignosulfonate and alcohol ethoxylates) are added and with the aid of technical equipment ( eg extrusion, spray tower, fluidized bed) are prepared as water-dispersible or water-soluble granules. Dilution with water gives a stable dispersion or solution of the active substance. vii) Water-dispersible powder and water-soluble powder (WP, SP, WS) 50-80% by weight of compounds I or II or mixtures according to the invention are ground in a rotor-stator mill with the addition of 1-5% by weight of a dispersant (for example sodium lignosulfonate), 1-3% by weight of a wetting agent ( such as alcohol ethoxylates) and up to 100% by weight solid carrier such as silica gel. Dilution with water gives a stable dispersion or solution of the active substance. viii) Gels (GW, GF) In an agitating ball mill, 5-25% by weight of compound I or II or mixtures according to the present invention are pulverized, 3-10% by weight of dispersants (such as sodium lignosulfonate), 1-5% by weight of thickeners ( For example carboxymethylcellulose) and up to 100% by weight of water give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance. ix) Microemulsion (ME) Add 5-20% by weight of compound I or II or mixture according to the invention to 5-30% by weight of organic solvent blend (such as fatty acid dimethylamide and cyclohexanone), 10-25% by weight of surfactant blend Compounds (such as alcohol ethoxylates and arylphenol ethoxylates) and water made up to 100%. This mixture was stirred for 1 hour to spontaneously generate a thermodynamically stable microemulsion. x) Microcapsules (CS) An oil phase comprising 5-50% by weight of compound I or II or a mixture according to the invention, 0-40% by weight of a water-insoluble organic solvent (such as an aromatic hydrocarbon), 2-15% by weight of an acrylic acid monomer (such as methacrylic acid Methyl esters, methacrylic acid and diacrylates or triacrylates) are dispersed in aqueous solutions of protective colloids such as polyvinyl alcohol. Free radical polymerization initiated by a free radical initiator leads to the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50% by weight of compound I or II or a mixture according to the invention, 0-40% by weight of a water-insoluble organic solvent (such as an aromatic hydrocarbon) and an isocyanate monomer (such as diphenylmethylene -4,4'-diisocyanate) dispersed in an aqueous solution of a protective colloid (such as polyvinyl alcohol). Addition of polyamines such as hexamethylenediamine results in the formation of polyurea microcapsules. The monomers amount to 1-10% by weight. The wt% relates to the total CS composition. xi) Spreadable powders (DP, DS) 1-10% by weight of compounds I or II or mixtures according to the invention are finely ground and intimately mixed with up to 100% by weight of a solid carrier (eg finely divided kaolin). xii) Granules (GR, FG) 0.5-30% by weight of compounds I or II or mixtures according to the invention are finely ground and associated with up to 100% by weight of solid carriers (eg silicates). Granulation is achieved by extrusion, spray drying or fluidized bed. xiii) Ultra Low Volume Liquid (UL) 1-50% by weight of compounds I or II or mixtures according to the invention are dissolved in up to 100% by weight of organic solvents (eg aromatic hydrocarbons).

Composition types i) to xi) optionally contain further auxiliaries, such as 0.1-1% by weight of bactericides, 5-15% by weight of antifreeze agents, 0.1-1% by weight of defoamers and 0.1-1% by weight of colorants.

The agrochemical compositions generally comprise 0.01 to 95% by weight, preferably 0.1 to 90% by weight and optimally 0.5 to 75% by weight of active substance. The purity of the active substances used is from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).

Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients and other pesticidal agents (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) can be added to the active substance or contained in the active Compositions of substances are used as premixes or, if appropriate, added immediately prior to use (tank mix). These agents can be mixed with the composition according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

The user usually applies the composition according to the invention from a pre-dose device, a knapsack sprayer, a spray tank, a spray plane or an irrigation system. As a rule, the agrochemical compositions are formulated with water, buffers and/or other auxiliaries to the desired application concentration, and thus a ready-to-use spray liquid or an agrochemical composition according to the invention is obtained. In general, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agriculturally useful area.

According to one embodiment, the individual components of the compositions according to the invention, such as parts of kits or parts of binary or ternary mixtures, can be mixed by the user himself in a spray tank and, if appropriate, further auxiliaries can be added.

In another embodiment, the individual components or partially premixed components of the composition according to the invention, for example comprising the compounds of the invention and/or the mixing partners as defined above, can be sprayed by the user Mix in the tank, and add other auxiliaries and additives if appropriate.

In another embodiment, the individual components or partially premixed components of the composition according to the invention, for example comprising the compounds of the invention and/or the mixing partners as defined above, may be used together (for example in after tank mixing) or continuous application.

Application method The compounds and mixtures according to the invention are suitable for protecting crops, plants, plant propagation material (such as seeds) or the soil or water in which plants are grown against attack or infestation by animal pests. Accordingly, the present invention also relates to a method for the protection of plants, which comprises contacting a crop, a plant, plant propagation material (such as seeds) or the soil or water in which a plant is growing, with a pesticidally effective amount of a compound according to the invention against attack or infestation by animal pests. dye.

The compounds and mixtures according to the invention are also suitable for combating or controlling animal pests. Accordingly, the present invention also relates to a method of combating or controlling animal pests, which comprises causing the animal pest, its habitat, breeding ground or food supply, or crops, plants, plant propagation material (such as seeds), or soil, Or an area, material or environment where an animal pest is growing or could grow is contacted with a pesticidally effective amount of a compound of the invention.

The compounds and mixtures of the invention are effective upon contact and ingestion. Furthermore, the compounds and mixtures of the invention may be administered to any and all developmental stages, such as eggs, larvae, pupae and adults.

The compounds and mixtures of the invention may be applied as such or in the form of compositions comprising them as defined above. Furthermore, the compounds and mixtures according to the invention can be applied together with mixture partners as defined above or in the form of compositions comprising such mixtures as defined above. The components of the mixture may be applied simultaneously, together or separately, or sequentially (i.e. one immediately after the other) to produce the mixture "in situ" at the desired location (e.g. the plant), in the case of separate applications the sequence is generally Has no effect on the outcome of the control measures.

Application can be performed before and after infestation of the crop, plant, plant propagation material (such as seeds), soil, or area, material or environment by the pest.

Suitable methods of application include, inter alia, soil treatment, seed treatment, in-furrow application, water-inlet application (for example in paddy fields during irrigation) and foliar application. Soil treatment methods include saturating the soil, drip irrigation (drip application to the soil), soaking the roots, tubers or bulbs, or soil injection. Seed treatment techniques include seed dressing, seed coating, seed dusting, seed soaking and seed pelleting. In-furrow application generally includes the steps of forming a furrow on arable land, sowing the furrow with seeds, applying the pesticidally active component I or II or the mixture to the furrow and sealing the furrow. Foliar application means the application of pesticidally active ingredients I or II or mixtures to the foliage of plants, for example via spray equipment. For foliar application, it may be advantageous to modify the behavior of pests by using pheromones in combination with the compounds and mixtures of the invention. Suitable pheromones for specific crops and pests are known to the skilled person and are publicly available from databases of pheromones and semiochemicals, such as http://www.pherobase.com.

As used herein, the term "contact" includes direct contact (applying the compound/composition directly to the animal pest or the plant - usually to the leaves, stems or roots of the plant) and indirect contact (applying the compound/composition to the animal pest The locus of an organism or plant, i.e. habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest is growing or may grow).

The term "animal pest" includes arthropods, gastropods and nematodes. Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, especially insects. Insects that are particularly associated with crops are often referred to as crop pests.

The term "crop" refers to grown and harvested crops.

The term "plant" includes cereals such as durum wheat and other wheats, rye, barley, triticale, oats, rice or corn (fodder corn and sugar corn/sweet corn and common corn); sugar beets such as sugar beets or fodder Beets; fruits such as pome, stone or soft fruit, such as apples, pears, plums, peaches, nectarines, almonds, cherries, papayas, strawberries, raspberries, blackberries or gooseberries; legumes such as beans, lentils, Peas, alfalfa or soybeans; oil plants such as rapeseed (rape), turnip rape, mustard, olives, sunflowers, coconuts, cocoa beans, castor oil plants, oil palms, peanuts or soybeans; melons such as pumpkins, pumpkins, Cucumbers or melons; fibrous plants such as cotton, flax, hemp or jute; citrus fruits such as oranges, lemons, grapefruits or tangerines; vegetables such as eggplants, spinach, lettuces (e.g. Asparagus, kale, carrots, onions, garlic, leeks, tomatoes, potatoes, gourds, or bell peppers; laurel plants, such as avocado, cinnamon, or camphor; energy and raw material plants, such as corn, soybeans, rapeseed, sugar cane, or oil Brown; tobacco; nuts, such as walnuts; pistachios; coffee; tea; bananas; vines (table grapes and grape must vines); hops; sweet leaves (also known as stevia); natural rubber plants or ornamental and forestry plants , such as flowers (e.g. carnations, petunias, geraniums/geraniums, pansies and impatiens), shrubs, broad-leaved trees (e.g. poplars) or evergreens such as conifers; eucalyptus; turf; lawns; grasses, such as for animals Forage or ornamental grass. Preferred plants include potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, beans, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables , such as cucumbers, tomatoes, beans or squash.

The term "plant" is understood to include wild-type plants as well as plants which have been modified by conventional breeding, or mutagenesis or genetic engineering, or by a combination thereof, in order to provide the plant with new traits or to modify existing traits.

Mutagenesis includes random mutagenesis techniques using X-rays or mutagenic chemical reagents, and targeted mutagenesis techniques to generate mutations at specific loci in the plant genome. Targeted mutagenesis techniques often use oligonucleotides or proteins such as CRISPR/Cas, zinc finger nucleases, TALENs, or meganucleases to achieve targeting.

Genetic engineering typically uses recombinant DNA techniques to produce modifications in plant genomes that cannot naturally be readily obtained by cross-breeding, mutagenesis, or natural recombination. Typically, one or more genes are integrated into the plant genome in order to increase or improve a trait. Such integrated genes are also referred to as transgenes in the art, and plants containing such transgenes are referred to as transgenic plants. The plant transformation process typically results in several transformation events that differ by the genomic locus into which the transgene has been integrated. A plant containing a particular transgene at a particular genomic locus is often described as containing a particular "event," which is referred to by a particular event name. Traits that have been introduced into plants or have been altered include, inter alia, herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions such as drought.

Herbicide tolerance is produced by using mutagenesis and by using genetic engineering. Plants that have been rendered tolerant to acetyl lactate synthase (ALS) inhibitor herbicides using conventional mutagenesis and breeding methods include the plant variety marketed under the name ^Clearfield® . However, most herbicide tolerance traits have been generated using transgenes.

Herbicides against glyphosate, glufosinate, 2,4-D, dicamba, oxynil (such as bromoxynil and ioxynil) have been produced )), sulfonylurea herbicides, ALS inhibitor herbicides and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors (such as isoxaflutole and mesotrione ) herbicide tolerance.

Transgenes that have been used to provide herbicide tolerance traits include: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621 and goxv247; Resistance: pat and bar; for tolerance to 2,4-D: aad-1 and aad-12; for tolerance to dicamba: dmo; for tolerance to benzonitrile herbicide: bxn; For tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA; for tolerance to ALS inhibitor herbicides: csr1-2; for HPPD inhibitor herbicide Drug tolerance: hppdPF, W336 and avhppd-03.

Transgenic maize events containing herbicide tolerance genes are as follows but not excluded: DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHG0JG, HCEM48 5. VCO-Ø1981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.

Transgenic soybean events containing herbicide tolerance genes are as follows but not excluded: GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547 -35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHTØH2, W62, W98, FG72, and CV127.

Transgenic cotton events containing herbicide tolerance genes are as follows but not excluded: 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.

Transgenic canola events including herbicide tolerance genes are as follows but not excluded: MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3 .

Insect resistance arises primarily by transferring bacterial genes for insecticidal proteins into plants. The most frequently used transgenes are toxin genes of Bacillus spec. and their synthetic variants, such as cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bbl, cry34Abl, cry35Abl, cry9C, vip3A(a), vip3Aa20. However, genes of plant origin have also been transferred into other plants. In particular, genes encoding protease inhibitors, such as CpTI and pinII. Another approach uses transgenes to produce double-stranded RNA in plants to target and down-regulate insect genes. An example of such a transgene is dvsnf7.

Transgenic maize events containing insecticidal protein or double-stranded RNA genes are as follows, but not excluded: 59122, TC1507, TC6275, CBH-351, MIR162, DBT418 and MZIR098.

Transgenic soybean events comprising an insecticidal protein gene are the following but not exclusive: MON87701, MON87751 and DAS-81419.

Transgenic cotton events containing insecticidal protein genes are as follows, but not excluded: 3. T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119 and SGK321.

Yield increases were achieved by increasing ear biomass using the transgene athbl7 present in maize event MON87403, or by enhancing photosynthesis using the transgene bbx32 present in soybean event MON87712.

Cultivar plants comprising improved oil content have been produced by using the following transgenes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769.

Tolerance to abiotic conditions, especially to drought, has been improved by using the transgene cspB contained in maize event MON87460 and by using the transgene Hahb- contained in soybean event IND-ØØ41Ø-5 4 generated.

Traits are often combined by combining genes in transformation events or by combining different events during the breeding process. Preferred combinations of traits are herbicide tolerance to different groups of herbicides; insect resistance to different species of insects, especially resistance to Lepidoptera and Coleoptera; herbicide tolerance in combination with one or several types of Insect resistance; herbicide tolerance and increased yield; and herbicide tolerance in combination with tolerance to abiotic conditions.

Plants comprising single or stacked traits and the genes and events that confer such traits are well known in the art. For example, detailed information on mutagenic or integrated genes and corresponding events is available from the International Service for the Acquisition of Agri-biotech Applications (ISAAA) (http://www. .isaaa.org/gmapprovaldatabase) and "Center for Environmental Risk Assessment (CERA)" (http://cera-gmc.org/GMCropDatabase) websites and patent applications, such as EP3028573 and WO2017/011288 obtained .

In one embodiment of the present invention, the plant is preferably a rice plant (Oryza spp., preferably Oryza sativa). Two types of rice are most commonly grown, Oryza glabra and Oryza glaberrima. Many subspecies of rice are commercially important, including indica rice (Oryza sativa subsp. indica), japonica rice (Oryza sativa subsp. japonica), Java rice (Oryza sativa subsp. javanica), glutinous rice (Oryza sativa subsp. glutinosa) (glutinous rice), aromatic rice (Oryza sativa Aromatica group) (eg basmati) and rice (floating rice).

Plants of particular commercial importance which have been modified by mutagenesis or genetic engineering include rice. In a plant that has been modified by mutagenesis or genetic engineering, one or more genes have been mutagenized or integrated into the genetic material of the plant. The one or more mutagenized or integrated genes are preferably selected from pat, epsps, cry1Ab, bar, cry1Fa2, cry1Ac, cry34Ab1, cry35AB1, cry3A, cryF, cry1F, mcry3a, cry2Ab2, cry3Bb1, cry1A.105, dfr, barnase , vip3Aa20, barstar, als, bxn, bp40, asn1 and ppo5. Mutagenesis or integration of one or more genes is performed to improve certain characteristics of the plant. Such traits, also known as traits, include abiotic stress tolerance, altered growth/yield, disease resistance, herbicide tolerance, insect resistance, improved product quality, and pollination control. Among these traits, herbicide tolerance, for example imidazolinone tolerance, glyphosate tolerance or immobilized herbicide tolerance, is of particular importance.

It has been unexpectedly found that the pesticidal activity of the compounds according to the invention can be enhanced by the insecticidal traits of the modified plants. Furthermore, the compounds according to the invention have been found to be useful for preventing insects from developing resistance to insecticidal traits or against pests which have become resistant to insecticidal traits in modified plants. Furthermore, the compounds according to the invention are useful against pests against which insecticidal traits are ineffective, so that supplementary insecticidal activity can advantageously be used.

The use of the compositions according to the invention on cultivated plants produces an effect specific for the cultivated plant comprising a certain gene or event. These effects may involve changes in growth behavior or changes in resistance to biotic or abiotic stress factors. Such effects may include, inter alia, increased yield, increased resistance or tolerance to insects, nematodes, fungi, bacteria, mycoplasma, viruses or viroid pathogens, as well as early vigor, early or delayed maturation, cold or heat tolerance, and altered Amino acid or fatty acid profile or content.

It has surprisingly been found that the pesticidal activity of the compounds and mixtures according to the invention can be enhanced by the insecticidal traits of the modified plants. Furthermore, it has been found that the compounds and mixtures according to the invention are suitable for preventing the development of resistance in insects to insecticidal traits or for combating pests which have become resistant to insecticidal traits in modified plants. Furthermore, the compounds and mixtures according to the invention are suitable for combating pests against which insecticidal traits are ineffective, so that supplementary insecticidal activity can advantageously be used.

The term "plant propagation material" refers to all reproductive parts of plants, such as seeds and vegetative plant material, such as cuttings and tubers (eg potatoes), which can be used for the propagation of plants. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, buds, shoots and other parts of plants. Seedlings and young plants transplanted after germination or after emergence from soil may also be included. Such plant propagation material can be treated prophylactically with plant protective compounds at or before planting or transplanting.

The term "seed" covers seeds and plant propagules of all kinds, including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruits, tubers, grains, cuttings, cuttings and the like, and In a preferred embodiment it means real seeds.

In general, "pesticidally effective amount" means the amount required to achieve an observable effect on growth, including necrosis, death, retardation, prevention and removal, destruction or otherwise reducing the presence and activity of the target organism. required amount of active ingredient. The pesticidally effective amount will vary for the various compounds/compositions used in the present invention. The pesticidally effective amount of the composition will also vary depending on prevailing conditions, such as the desired pesticidal effect and duration, weather, target species, location, mode of application, and the like.

In the case of soil treatment, furrow application or application to pest habitats or nests, the amount of active ingredient is in the range of 0.0001 to 500 g/100 m ² , preferably 0.001 to 20 g/100 m ² .

For use in the treatment of crop plants, for example by foliar application, the active ingredient according to the invention may be applied at a rate of from 0.0001 g to 4000 g per hectare, for example from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare, ideally 1 g to 100 g per hectare, more desirably 10 to 50 g per hectare, for example 10 to 20 g per hectare, 20 to 30 g per hectare, 30 to 40 g per hectare or 40 to 50 g per hectare .

The compounds and mixtures according to the invention are particularly suitable for the treatment of seeds in order to protect the seeds from pests, especially soil-dwelling pests, and the roots and shoots of the resulting seedlings against soil pests and foliar insects. Accordingly, the present invention also relates to a method for protecting seeds from insects, especially soil insects, and protecting roots and shoots of seedlings from insects, especially soil and foliar insects, which method comprises the use of the present invention before sowing and/or after priming. Compounds to treat seeds. It is better to protect the roots and shoots of the seedlings. Better to protect seedling shoots from sucking insects, chewing insects and nematodes.

The term "seed treatment" includes all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, seed pelleting and furrow application methods. Preferably, the seed treatment application of the active compounds I or II or of the mixtures is carried out by spraying or by dusting the plants before sowing of the plants and before emergence of the plants.

The invention also encompasses seeds coated or containing active ingredient I or mixtures thereof. The term "coated with and/or containing" generally means that the active ingredient is mostly on the surface of the propagation product at the time of application, although a greater or lesser portion of the ingredient may penetrate into the propagation product, depending on the method of application. When the propagation product is (re)planted, it can absorb the active ingredient.

The invention also includes compositions comprising seeds and active ingredient I or mixtures thereof.

The invention also encompasses compositions comprising seeds and active non-racemic compound I or mixtures thereof.

The invention also comprises compositions comprising seed and active compound I in enantiomeric excess of compound I-R, preferably compound I-1 in enantiomeric excess of compound I-R-1 or mixtures thereof.

The invention also includes compositions comprising seeds and active compound I-R, preferred compound I-R-1 or mixtures thereof.

Suitable seeds are, for example, seeds of cereals, root crops, oil crops, vegetables, spices, ornamental plants, such as durum wheat and other wheat, barley, oats, rye, corn (fodder corn and sugar corn/sweet corn and common corn) ), soybeans, oil plants, cruciferous plants, cotton, sunflower, banana, rice, rapeseed, turnip rape, sugar beet, fodder beet, eggplant, potato, grass, lawn, turf, fodder grass, tomato, leek, pumpkin/ Pumpkins, kale, iceberg lettuce, peppers, cucumbers, melons, Brassicas, melons, beans, peas, garlic, onions, carrots, tubers such as potatoes, sugar cane, tobacco, grapes, petunias, geraniums/geraniums, Seeds of pansies and impatiens.

In addition, the active compounds can also be used for the treatment of seed from plants which have been modified by mutagenesis or genetic engineering and which are, for example, resistant to the action of herbicides or fungicides or insecticides. Such modified plants are described in detail above.

Conventional seed treatment formulations include, for example, flowable concentrates FS, solutions LS, suspoemulsions (SE), powders DS for dry treatment, water-dispersible powders WS for slurry treatment, water-soluble powders SS and emulsions ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seed lines is carried out directly on the seeds before sowing or after priming the seeds. Preferably, the formulation is applied such that germination is not involved.

The active substance concentration in the ready-to-use formulations obtainable after two to ten-fold dilution is preferably from 0.01 to 60% by weight, more preferably from 0.1 to 40% by weight.

In a preferred embodiment, the FS formulation is used for seed treatment. Typically, FS formulations may comprise 1-800 g/l active ingredient, 1-200 g/l surfactant, 0 to 200 g/l antifreeze, 0 to 400 g/l binder, 0 to 200 g/l Pigment and up to 1 liter of solvent, preferably water.

Particularly preferred FS formulations of the compounds and mixtures according to the invention for seed treatment generally comprise 0.1 to 80% by weight (1 to 800 g/l) active ingredient, 0.1 to 20% by weight (1 to 200 g/l) at least one surfactant, e.g. 0.05 to 5% by weight wetting agent and 0.5 to 15% by weight dispersant, up to 20% by weight, e.g. 5 to 20% antifreeze, 0 to 15% by weight, e.g. 1 to 15% by weight pigment and / or dyes, 0 to 40% by weight, for example 1 to 40% by weight binder (adhesive), optionally up to 5% by weight, for example 0.1 to 5% by weight thickener, optionally 0.1 to 2% defoamer, And optionally preservatives, such as biocides, antioxidants or the like, for example in an amount of 0.01 to 1% by weight, and fillers/vehicles up to 100% by weight.

In seed treatment, the application rate of the compound of the present invention is generally 0.1 g to 10 kg per 100 kg of seeds, preferably 1 g to 5 kg per 100 kg of seeds, more preferably 1 g to 1000 g per 100 kg of seeds and especially per 100 kg of seeds 1 g to 200 g per kg seed, eg 1 g to 100 g or 5 g to 100 g per 100 kg seed.

Accordingly, the present invention also relates to seeds comprising a compound of the invention or an agriculturally useful salt of the salt as defined herein. The amount of the compound of the present invention or its agriculturally useful salt generally varies within the range of 0.1 g to 10 kg per 100 kg of seeds, preferably 1 g to 5 kg per 100 kg of seeds, especially 1 g to 1000 g per 100 kg of seeds . For certain crops (such as lettuce), the ratio may be higher.

The compounds and mixtures of the invention can also be used to improve the health of plants. Accordingly, the present invention also relates to a method for improving the health of plants by treating plants, plant propagation material and/or the locus where plants grow or are to grow with an effective and non-phytotoxic amount of the compounds according to the invention.

As used herein, "effective and non-phytotoxic amount" means that component I or II or the mixture is used in an amount which allows the desired effect to be obtained, but which does not appear on the treated plants or from the treated propagules or treated produce any phytotoxic symptoms on plants grown in the same soil.

The terms "plant" and "plant propagation material" are as defined above.

"Plant health" is defined as the condition of a plant and/or its products, which is determined by several aspects alone or in combination with each other, such as yield (for example increased biomass and/or increased content of valuable components), quality (e.g. improved content or composition of certain ingredients or shelf life), plant vigor (e.g. improved plant growth and/or greener leaves (“greening effect”), response to abiotic (e.g. drought) and/or biotic stress ( eg disease) resistance and production efficiency (eg harvest efficiency, processability).

The above-identified indicators of plant health can be interdependent and can be generated from each other. Each index is defined in the art and can be determined by methods known to the skilled person.

The compounds of the invention are also suitable for use against non-crop pests. To target such non-crop pests, the compounds and mixtures of the invention can be used as bait compositions, gels, general insect sprays, aerosols, as ultra-low volume applications and mosquito nets (dipping or surface application). In addition, soak and channel methods can be used.

As used herein, the term "non-crop pest" refers to pests particularly associated with non-crop targets, such as ants, termites, wasps, flies, ticks, mosquitoes, crickets or cockroaches, preferably mosquitoes, more preferably yellow fever mosquitoes.

The bait may be a liquid, solid or semi-solid formulation (eg gel). The bait employed in the composition is a product that is attractive enough to induce the consumption of insects such as ants, termites, wasps, flies, mosquitoes, crickets, etc. or cockroaches. Attraction can be manipulated through the use of feeding stimulants or sex pheromones. Food stimulants are selected from, for example but not limited to, animal and/or vegetable proteins (meat meal, fish meal or blood meal, insect parts, egg yolk), fats and oils of animal and/or vegetable origin, or monosaccharides, oligosaccharides or polysaccharides, especially sucrose , lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decayed parts of fruits, crops, plants, animals, insects or specific parts thereof may also act as feeding stimulants. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature (eg http://www.pherobase.com) and are known to those skilled in the art.

For use in erbium bait compositions, the typical content of active ingredient is 0.001% to 15% by weight, ideally 0.001% to 5% by weight of active ingredient I or mixtures.

Formulations of the compounds and mixtures of the invention in the form of aerosols (eg spray cans), oil sprays or pump sprays are well suited for the lay user to control pests such as flies, fleas, ticks, mosquitos or cockroaches. Aerosol formulations preferably consist of the active compounds I or mixtures, solvents, other auxiliaries such as emulsifiers, perfume oils, if appropriate stabilizers and, if necessary, propellants.

Oil spray formulations differ from aerosol formulations in that no propellants are used.

For spray compositions, the content of active ingredient is 0.001 to 80% by weight, preferably 0.01 to 50% by weight and most preferably 0.01 to 15% by weight.

The compounds and mixtures of the present invention and their corresponding compositions can also be used in mosquito coils and fumigation coils, cigarette cases, evaporator plates or long-term evaporators, and also in evaporator paper, evaporator pads or other evaporator systems that do not rely on heating .

The method of controlling infectious diseases transmitted by insects, such as malaria, dengue and yellow fever, lymphatic filariasis and leishmaniasis, using the compounds and mixtures of the present invention and their corresponding compositions also comprises the treatment of sheds and house surfaces , air sprayed and impregnated curtains, tents, clothing, mosquito nets, tsetse traps or the like. Insecticidal compositions for application to fibres, fabrics, knits, nonwovens, netting materials or foils and tarpaulins preferably comprise a mixture comprising an insecticide, optionally a repellent and at least one binder.

The compounds and mixtures of the present invention and compositions thereof can be used for the protection of wooden materials such as trees, wooden fences, sleepers, frames, works of art, etc. and buildings, and also for the protection of construction materials, furniture, leather, fibers, vinyl products , wires and cables, etc. from ants and/or termites, and to control ants and termites that cause damage to crops or humans (such as when pests invade houses and public facilities).

Customary application rates in material protection are, for example, 0.001 g to 2000 g or 0.01 g to 1000 g of active ingredient I or the mixture per m ² of treated material, ideally 0.1 g to 50 g/m ² .

Insecticidal compositions for impregnating materials generally contain 0.001 to 95% by weight, preferably 0.1 to 45% by weight and more preferably 1 to 25% by weight of at least one repellent and/or insecticide.

Pests The compounds of the present invention are especially useful against animal pests such as arthropods, gastropods and nematodes, including but not limited to: Lepidoptera, such as the small wax moth ( Achroia grisella ); spp.), such as A. fimbriana , A. gloverana , A. variana , A. variana ; Acrolepiopsis assectella ); Acronicta major ( Acronicta major ); Adoxophyes spp ( Adoxophyes spp), such as A. cyrtosema , A. orana ; Aedia leucomelas ); cutcuts ( Agrotis spp.), such as police cutcut ( A. exclamationis ), Yanqing cutcut ( A. fucosa ), lesser cutcut ( A. ipsilon ), western gray cutworm ( A. orthogoma ), yellow cutworm ( A. segetum ), and grain-skinned cutworm ( A. subterranea ); cotton leaf moth ( Alabama argillacea ); spiral whitefly ( Aleurodicus dispersus ); Pauline inchworm ( Alsophila pometaria ); Horn moth ( Ampelophaga rubiginosa ); Navel orange borer ( Amyelois transitella ); White shoulder moth ( Anacampsis sarcitella ); Mediterranean mealy moth ( Anagasta kuehniella ); ; Antheraea pernyi ; Anticarsia (=Thermesia) spp., such as A. gemmatalis ; Apamea spp. ; Aproaerema modicella ; ; Archips spp., such as A. argyrospila , A. fuscocupreanus , A. rosana , A. xyloseanus Argyrestia conjugella ( Argyresthia conjugella ); Argyroploce spp.; Argyrotaenia spp, such as A. velutinana ; Athetis mindara ; Cotton leafhopper ( Austroasca viridigrisea ); Autographa gamma ; Autographa nigrisigna ; Cabbage armyworm ( Barathra brassicae ); Leafminer ( Bedelia spp. ); Borer ( Bonagota salubricola ); Indica butterfly ( Borbo cinnara ); Cotton leaf piercer ( Bucculatrix thurberiella ); Pine looper ( Bupalus piniarius ); Brown moth ( Busseola spp.); Leaf tortrix ( Cacoecia spp. ), such as C. murinana, C. podana ; Cactoblastis cactorum; Cadra cautella ; Calingo braziliensis ; tea Caloptilis theivora ; Capua reticulana ; Carposina spp., such as C. niponensis , C. sasakii ; Cephus spp. .) ; Chaetocnema aridula ; Cheimatobia brumata ; Chilo spp, such as C. Indicus , C. suppressalis , Grass moth ( C. partellus ); Apple moth ( Choreutis pariana ); Choristoneura spp., such as willow moth ( C. conflictana ), spruce moth ( C. fumiferana ), apple moth Leaf tortrix ( C. longicellana ), European spruce leaf tortrix ( C. murinana ), western spruce tortrix ( C. occidentalis ), rose tortrix ( C. rosaceana ) ; Pseu-doplusia) spp.), such as C. eriosoma , C. includens ; Cirphis unipuncta ; Clysia ambiguella ; Clysia ambiguella ; Cnaphalocerus spp.); Cnaphalocerus medinalis ; Cnephasia spp.; Cochylis hospes ; Coleophora spp.; Colias eurytheme ; Conopomorpha spp.; Conotrachelus spp.; Copitarsia spp.; Corcyra cephalonica ; Crambus caliginosellus ; Crambus teterrellus ); bean rootworm ( Crocidosema (=Epinotia) aporema ) ; boxwood moth ( Cydalima ( =Diaphania) perspectivelis ); , Nut leaf tortrix ( C. latiferreana ); Dalaca noctuides ; Walnut with chip boat moth ( Datana integerrima ); pine poison moth ( Dasychira pinicola ); pine caterpillar ( Dendrolimus spp.), such as European pine caterpillar ( D. pini ), Red pine caterpillar ( D. spectabilis ), larch caterpillar ( D. sibiricus ); grape leaf roller ( Desmia funeralis ); silk borer ( Diaphania spp.), such as cucumber silk borer ( D. nitidalis ), melon silkworm D. hyalinata ; Diatraea grandiosella ; Diatraea saccharalis ; Diphthera festiva ; Earias spp . E. insulana ), E. vittella ; citrus fruit borer ( Ecdytolopha aurantianu ); citrus groundworm ( Egira (=Xylomyges) curialis ); South American corn seedling borer ( Elasmopalpus lignosellus ); sugarcane borer ( Eldana saccharina ); grape borer ( Endopiza viteana ); elm autumn yellow-foot moth ( Ennomos subsignaria ); Mexican rice borer ( Eoreuma loftini ); E. elutella , E. kuehniella ; Epinotia aporema ; Epiphyas postvittana ; Erannis tiliaria ; Erionota thrax ); Etiella spp.; Eulia spp.; Eupoecilia ambiguella ; Euproctis chrysorrhoea ; Euxoa spp.; Evetria bouliana ; Faronta albilinea , Feltia spp., such as F. Subterranean ; Galleria mellonella , Gracillaria spp. ), Grapholita spp., such as Li small borer ( G.funebrana ), pear small borer ( G.molesta ), apple small borer ( G.inopinata ); Halysidota spp., Harrisina americana , Hedylepta spp., bell Helicoverpa spp., such as H. armigera ( = Heliothis armigera) ), H. zea ( = Heliothis zea ) ; Heliothis spp., such as tobacco Hellula spp. , such as H.undalis and H.rogatalis ; Helocoverpa gelotopoeon , Silkworm moth ( Hemileuca oliviae ), Rice leaf-cutting borer ( Herpetogramma licarsisalis ), Hibernia defoliaria , Brown weaver moth ( Hofmannophila pseudospretella ), Sunflower spot borer ( Homoeosoma electellum ), Tea tumbler moth ( Homona magnanima ), Green spider moth ( Hypena scabra ), American white moth ( Hyphantria cunea ), cherry nest moth ( Hyponomeuta padella ), apple nest moth ( Hyponomeuta malellus ), kaki pedicle moth ( Kakivoria flavofasciata ), tomato moth ( Keiferia lycopersicella ), hemlock looper moth ( Lambdina fiscelaria fiscellaria ), western hemlock looper moth ( Lambdina fiscellaria lugubrosa ), bean leaf roller ( Lamprosema indicata ), silverfish borer ( Laspeyresia molesta ), soybean borer ( Leguminivora glycinivorella ), rice leaf roller ( Lerodea eufala ), nightshade Leucinodes orbonalis , Leucoma salicis , Leucoptera spp. such as L. coffeella , L. scitella ; Leumivora lycinivorella , apple-spotted Leaf miner ( Lithocolletis blancardella ), green fruit winter armyworm ( Lithophane antennata ), soybean armyworm ( Llattia octo ( = Amyna axis ) ), grape berry tortillaria ( Lobesia botrana ), Lophocampa spp., bean white longcut Rootworm ( Loxagrotis albicosta ), Loxostege spp., such as L. sticticalis , L. cereralis ; Lymantria spp., such as L. dispar , L. .monacha ); Lyonetia clerkella , Lyonetia prunifoliella , Malacosoma spp., such as M.americanum , M.californicum ), forest canopy caterpillar ( M.constrictum ), tawny canopy caterpillar ( M.neustria ); noctuid genus ( Mamestra spp.), such as cabbage moth ( M.brassicae ), scalloped moth ( M.configurata ); Mamstra brassicae , Manduca spp., such as tomato hornworm ( M.quinquemaculata ), tobacco hornworm ( M.sexta ); brush beetle moth ( Marasmia spp), Marmara spp., bean pod borer ( Maruca testulalis ), Megalopyge lanata , Melanchra picta , Melanitis leda , Mocis spp., such as M.lapites , M.repanda ; Mocis latipes , Monochroa fragariae , Mythimna separata , Nemapogon cloacella , Neoleucinodes elegantalis , Nepytia spp., Nymphula spp., Oiketicus spp., Omiodes indicata , Omphisa spp. anastomosalis ), winter looper moth ( Operophtera brumata ), Douglas moth ( Orgyia pseudotsugata ), Oria spp., thick beetle moth ( Orthaga thyrisalis ), stalk moth ( Ostrinia spp.), such as the European corn borer ( O. nubilalis ); rice leaf beetle ( Oulema oryzae ), spring inchworm ( Paleacrita vernata ), winter armyworm ( Panolis flammea ), rice beetle ( Parnara spp. ), stem borer ( Papaipema nebris ), great swallowtail butterfly ( Papilio cresphontes ), navel orange borer moth ( Paramyelois transitella ), grape piercing moth ( Paranthrene regalis ), palmless butterfly moth ( Paysandisia archon ), pink bollworm ( Pectinophora spp.), such as red bollworm ( P. gossypiella ); Peridroma saucia , Perileucoptera spp., such as P. coffeeella ; Phalera bucephala , Phryganidia californica , Phthorimaea spp. , such as potato tuber moth ( P.operculella ); citrus miner ( Phyllocnistis citrella ), small miner ( Phyllonorycter spp.), such as spotted leafminer ( P.blancardella ), hawthorn leafminer ( P. crataegella ), P.issikii , P. ringoniella ; Pieris spp., such as P.brassicae , P.rapae , P.napi ); Pilocrocis tripunctata , Plathypena scabra , Platynota spp., such as P.flavedana , P.idaeusalis , P. moth ( P.stultana ); carnation moth ( Platyptilia carduidactyla ), bean ash butterfly ( Plebejus argus ), Indian meal moth ( Plodia interpunctella ), silver leaf moth ( Plusia spp), diamondback moth ( Plutella maculipennis ), Plutella xylostella , Pontia protodica , Prays spp., Prodenia spp., Proxenus lepigone , Pseudaletia spp., such as Moth ( P.sequax ), one-star armyworm ( P.unipuncta ); corn borer ( Pyrausta nubilalis ), mint gray armyworm ( Rachiplusia nu ), Richia albicosta , dark ladybug ( Rhizobius ventralis ), American pine moth ( Rhyacionia frustrana ), diseased inchworm ( Sabulodes aegrotata ), red mountain back boat moth ( Schizura concinna ), rice brown edge moth ( Schoenobius spp.), Schreckensteinia festaliella , white grass moth ( Scirpophaga spp.), such as rice stem borer (S.incertulas), S.innotata ; yellow cutworm ( Scotia segetum ), Sesamia spp., such as rice borer ( S.inferens ), grape tiger moth ( Seudyra subflava ), wheat moth ( Sitotroga cerealella ), Sparganothis pilleriana , Spilonota lechriaspis, S.ocellana , Spodoptera ( = Lamphygma) spp.), such as S.cosmoides , subtropical armyworm ( S.eridania ), beet armyworm ( S.exigua ), grass armyworm ( S.frugiperda ), S.latisfascia , sea gray wingworm ( S.littoralis ), litura ( S.litura ), S.omithogalli ; Stigmella spp., Stomopteryx subsecivella , Strymon bazochii , Syepta derogata , Pteroptera ( Synanthedon spp.), such as the small peach winged moth ( S.exitiosa ), Andean potato tuber moth ( Tecia solanivora ), Telehin licus , Thaumatopoea pityocampa , apple shaped small tumbler moth ( Thaumatotibia (=Cryptophlebia) leucotreta ), pine different boat moth ( Thaumetopoea pityocampa ), Thecla spp., Theresimima ampelophaga , Thyrinteina spp, Tildenia inconspicuella , Tinea spp., T. Cloacella , T. spp. ( T. Pellionella ); clothes moth ( Tineola bisselliella ), leaf tortrix ( Tortrix spp.), such as oak green tortrix ( T. Viridana ); felt clothes moth ( Trichophaga tapetzella ), trichoplusia spp. .), such as T. ni ; Tuta (=Scrobipal-pula) absoluta , Udea spp., such as U. rubigalis , Greenhouse netting borer ( U. rubigalis ); gray butterfly genus ( Viracola spp.), apple nest moth ( Yponomeuta padella ) and spruce liner moth ( Zeiraphera canadensis ); Coleoptera insects such as the striped cucumber beetle ( Acalymma vittatum ), Acanthoscehdes obtectus , Adoretus spp., Agelastica alni , Agrilus spp., such as A. anxius , A. Planipennis , A. sinuatus ; Agriotes spp., such as A. fuscicollis , A. lineatus , A. obscurus ; Alphitobius diaperinus , Amphimallus solstitialis , Anisandrus dispar , Anisoplia austriaca , Anobium punctatum , Aeruginosa beetle ( Anomala corpulenta ), red copper beetle ( Anomala rufocuprea ), star beetle ( Anoplophora spp.), such as glabripennis ( A. glabripennis ); flower elephant ( Anthonomus spp.), such as pepper flower elephant ( A. eugenii ) , cotton boll weevil ( A. grandis ), apple flower elephant ( A. pomorum ); genus Anthrenus spp., Aphthona euphoridae , genus Apion spp., genus Apogonia spp. ), Athous haemorrhoidalis , Atomaria spp., such as A. linearis ; Attagenus spp., Aulacophora femoralis , A. Blastophagus piniperda ), Blitophaga undata , Bruchidius obtectus ( Bruchidius obtectus ), Bruchus spp., such as B. lentis , B. pisorum , B. rufimanus ); pear leafroll weevil ( Byctiscus betulae ), red-winged beetle beetle ( Callidiellum rufipenne ), Callopistria floridensis , mung bean weevil ( Callosobruchus chinensis ), European horse chestnut leafminer ( Cameraria ohridella ), sugar beet giant tortoise beetle ( Cassida nebulosa ), bean leaf Cerotoma trifurcata , Cetonia aurata , Ceuthorhynchus spp., such as C.assimilis , C.napi ; Chaetocnema tibialis ), Cleonus mendicus , Conoderus spp., such as C. vespertinus ; Conotrachelus nenuphar , Cosmopolites spp., brown New Zealand rib Costelytra zealandica, Crioceris asparagi , Cryptolestes ferrugineus , Cryptorhynchus lapathi , Ctenicera spp., such as C. destructor ; Curculio spp., Cylindrocopturus spp., Cyclocephala spp., Dactylispa balyi , Dectes texanus , Dermestes spp.), root leaf beetle ( Diabrotica spp.), such as cucumber eleven-star leaf beetle ( D.undecimpunctata ), South American leaf beetle ( D.speciosa ), long-horned leaf beetle ( D.longicornis ), D.semipunctata , Corn root leaf beetle ( D.virgifera ); citrus weevil ( Diaprepes abbreviates ), surname wild borer ( Dichocrocis spp.), rice iron beetle ( Dicladispa armigera ), Argentine roundworm ( Diloboderus abderus ), coconut flower two spots Elephant ( Diocalandra frumenti ( Diocalandra stigmaticollis ) ), oak beetle ( Enaphalodes rufulus ), plant-eating ladybug ( Epilachna spp.), such as Mexican bean ladybug ( E.varivestis ), potato ladybug ( E.vigintioctomaculata ); Epitrix spp., such as E. hirtipennis , E. similaris ; Eutheola humilis , Eutinobothrus brasiliensis , Faustinus cubae , naked spider beetle ( Gibbium psylloides ), Gnathocerus cornutus , Hellula undalis , Heteronychus arator , Hylamorpha elegans , Hylobius abietis , Hylotrupes bajulus , leaf Hypera spp., such as H. brunneipennis , H. postica ; Hypomeces squamosus , Hypothenemus spp., spruce Ips typographus , Lachnosterna consanguinea , Lasioderma serricorne , Latheticus oryzae , Lathridius spp., Lathridius spp. ( Lema spp.), such as tobacco beetle ( L. bilineata ), black horned mud beetle ( L. melanopus ); Leptinotarsa spp., such as potato beetle ( L.decemlineata ); Leptispa pygmaea , Limonius californicus , Lissorhoptrus oryzophilus , Lixus spp., Luperodes spp., Lyctus spp., such as the brown beetle ( L.bruneus ); Falk beetle ( Liogenys fuscus ), Macrodactylus spp., such as rose thorn beetle ( M. subspinosus ); Maladera matrida , Megaplatypus mutates , Megascelis spp., Melanotus communis , Meligethes spp., such as rapeseed beetle ( M.aeneus ); gill beetle ( Melolontha spp.), such as chestnut beetle ( M. hippocastani ), western May beetle ( M. melolontha ); West Indian sugarcane borer ( Metamasius hemipterus ), Microtheca spp., Migdolus spp., such as M.fryanus , Monochamus spp., such as M. alternatus ; South American fruit tree weevil ( Naupactus xanthographus ), yellow spider beetle ( Niptus hololeucus ), Oberia brevis , Oemona hirta , coconut rhinoceros beetle ( Oryctes rhinoceros ), saw chest mealworm ( Oryzaephilus surinamensis ), Oryzaphagus oryzae , black grape-eared elephant ( Otiorrhynchus sulcatus ), strawberries Root weevil ( Otiorrhynchus ovatus ), black grape ear weevil ( Otiorrhynchus sulcatus ), black-horned mud worm ( Oulema melanopus ), rice mud worm ( Oulema oryzae ), small blue-and-white beetle ( Oxycetonia jucunda ), ape leaf beetle ( Phaedon spp.), such as P. brassicae , P. cochleariae ; Phoracantha recurva , Phyllobius pyri , Phyllopertha horticola , Phyllophaga spp., such as P. helleri ; Phyllotreta spp., such as P. chrysocephala , P. nemorum , yellow-curled beetle ( P.striolata ), yellow striped flea beetle ( P.vittula ); garden beetle ( Phyllopertha horticola ), Japanese beetle ( Popillia japonica ), small weevil ( Premnotrypes spp. ), yellow star beetle ( Psacothea hilaris ) , Psylliodes chrysocephala , Prostephanus truncates , Psylliodes spp., Ptinus spp., Pulga saltona , Rhizopertha dominica , Cryptorhiza ( Rhynchophorus spp.), such as R.billineatus , red palm weevil ( R.ferrugineus ), palm weevil ( R.palmarum ), purple palm weevil ( R.phoenicis ), subpalm weevil ( R.vulneratus ); Apple wedge beetle ( Saperda candida ), navel beetle ( Scolytus schevyrewi ), sisal weevil ( Scyphophorus acupunctatus ), pea root nodule ( Sitona lineatus ), weevil ( Sitophilus spp.), such as grain weevil ( S. granaria ), rice elephant ( S.oryzae ), corn elephant ( S.zeamais ); Sphenophorus spp., such as S.levis ; Stegobium panicum , stem elephant ( Sternechus spp. ), such as soybean stem elephant ( S.subsignatus ); Strophomorphus ctenotus , Symphyletes spp., Tanymecus spp., Tenebrio molitor, Tenebrioides mauretanicus ; ( Tribolium spp.), such as T. castaneum; Trogoderma spp., Tychius spp., Xylotrechus spp., such as grape tiger Beetles ( X.pyrrhoderus ); and Zabrus spp., such as Z. Tenebrioides ; Diptera insects, such as Aedes spp., such as Egypt Aedes mosquito ( A. aegypti ), Aedes albopictus ( A. albopictus ), Aedes mosquito ( A. vexans ); Mexican fruit fly ( Anastrepha ludens ); Anopheles spp., such as Anopheles albopedes ( A.albimanus ), Anopheles disaster ( A.crucians ), Anopheles fischii ( A.freeborni ), Anopheles gambiae ( A.gambiae ), Anopheles white ankle ( A.leucosphyrus ), Anopheles five spots ( A. .maculipennis ), A.minimus , A.quadrimaculatus , A.sinensis ; Bactrocera invadens , Bibio hortulanus , green-headed Calliphora erythrocephala , Calliphora vicina , Ceratitis capitata , Chrysomyia spp., such as C.bezziana , C.hominivorax , C. macellaria ); Atlantic fly ( Chrysops atlanticus ), deer fly ( Chrysops discalis ), quiet spot fly ( Chrysops silacea ), cone fly ( Cochliomyia spp. ), such as screw fly ( C. hominivorax ); spp.), such as C. sorghicola; Cordylobia anthropophaga , Culex spp., such as C. nigripalpus , C. pipiens ) , Culicoides furens , Culiseta inornata , Culiseta melanura , Cuterebra spp., Dacus cucurbitae , Dacus oleae , Dasineura brassicae , Dasineura oxycoccana , Dasineura oxycoccana ( Delia spp.), such as onion fly ( D.antique ), corn fly ( D.coarctata ), gray field fly ( D.platura ), cabbage fly ( D.radicum ); human skin fly ( Dermatobia hominis ), Drosophila spp . , such as Drosophila spp. ( D. suzukii ), Fannia spp., such as F. canicularis ); ), such as G. intestinalis ; Geomyza tipunctata , Glossina spp., such as G. fuscipes , G. morsitans , G. palpalis , G. tachinoides , Haematobia irritans , Haplodiplosis equestris , Hippelates spp., Hylemyia spp., such as peanut field fly ( H.platura ); Hypoderma spp., such as H. lineata ; Hyppobosca spp., Hydrellia philippina , Leptoconops torrens , Liriomyza spp., such as L. sativae , L. trifolii ; Lucilia spp., such as L. caprina , Lucilia copper fly ( L. .cuprina ), Lucilia sericata ( L.sericata ); Lycoria pectoralis , Mansonia titillanus , Mayetiola spp., such as M.destructor ; Musca spp., such as Qiujia M.autumnalis , M.domestica ; Muscina stabulans ; Oestrus spp., such as O.ovis ; Opomyza florum , Oscinella spp.), such as Swedish straw fly ( O. frit ); rice gall midge ( Orseolia oryzae ), hysocyami spring fly ( Pegomya hysocyami ), silver-footed sandfly ( Phlebotomus argentipes ), Phorbia spp. , such as P.antiqua , P.brassicae , P.coarctata ; Phytomyza gymnostoma , Prosimulium mixtum , Psila rosae , Colombia Psorophora columbiae , Psorophora discolor , Rhagoletis spp., such as R. cerasi , R. cingulate , western cherry fruit fly ( R. indifferentens ), blue fruit fly ( R. .mendax ), apple fruit fly ( R. pomonella ); Rivellia quadrifasciata , Sarcophaga spp., such as red-tailed fly ( S. haemorrhoidalis ); gnat ( Simulium vittatum ), wheat red midge ( Sitodiplosis mosellana ), biting fly Stomoxys spp., such as S. calcitrans ; Tabanus spp., such as T. atratus , T. bovinus , T. lineola , T.similis ; Tannia spp., Thecodiplosis japonensis , Tipula oleracea , Tipula paludosa , and Wohlfahrtia spp.; Thysanoptera insects, such as Rice thrips ( Baliothrips biformis ), orchid thrips ( Dichromothrips corbetti ), Dichromothrips ssp., American spiny thrips ( Echinothrips americanus ), Enneothrips flavens , flower thrips ( Frankliniella spp.), such as brown thrips ( F. fusca ), F. occidentalis , F. tritici ; Heliothrips spp., Hercinothrips femoralis , Kakothrips spp. , Microcephalothrips abdominalis , Neohydatothrips samayunkur , Pezothrips kellyanus , Rhipiphorothrips cruentatus , Scirtothrips spp. , such as orange hard thrips ( S.citri ), small yellow thrips ( S.dorsalis ), avocado thrips ( S.perseae ); straight mane thrips ( Stenchaetothrips spp), Taeniothrips cardamoni , pear band thrips ( Taeniothrips inconsequens ); Thrips spp., such as T. imagines , T. hawaiiensis , T. oryzae , T. palmi ), T. parvispinus , T. tabaci ; Hemiptera insects such as Acizzia jamatonica , Acrosternum spp. such as A. hilare Acyrthosipon spp. such as A. onobrychis , A. pisum ; Adelges laricis , Adelges tsugae , Adelphocoris spp .), such as A. rapidus , A. superbus ; Aeneolamia spp., Agonoscena spp., Aulacorthum solani , Aleurocanthus woglumi , Aleurodes spp., Aleurodicus disperses , Aleurolobus barodensis , Aleurothrixus spp., Amrasca spp., Squash edge Stinkbugs ( Anasa tristis ), Antestiopsis spp. , Anuraphis cardui , Aonidiella spp. , Aphanostigma piri , Aphidula nasturtii , Aphids ( Aphis spp.), such as alfalfa aphid ( A. craccivora ), sugar beet aphid ( A. fabae ), strawberry root aphid ( A. forbesi ), cotton aphid ( A. gossypii ), North American tea currant aphid ( A. grossulariae ) , corn root aphid ( A. maidradicis ), apple aphid ( A. pomi ), elderberry aphid ( A. sambuci ), schneideri ( A. schneideri ), leaf roller aphid ( A. spiraecola ); grape leafhopper ( Arboridia apicalis ), Arilus critatus , Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacaspis yasumatsui , Solanum Aulacorthum solani , Bactericera cockerelli (Patrioza cockerelli) , whitefly ( Bemisia spp.), such as silverleaf whitefly ( B. argentifolii ), tabaci ( B. tabaci (Aleurodes tabaci) ); Blissus spp., such as B. leucopterus ; Brachycaudus spp., such as B. cardui , B. helichrysi , Peach aphid ( B. persicae ), B. prunicola ; Brachycolus spp., Brachycorynella asparagi , cabbage aphid ( Brevicoryne brassicae ), Cacopsylla spp., such as C. fulguralis , pear psyllid C. pyricola (Psylla piri) ; small brown rice lice ( Caligypona marginata ), genus Calocoris spp., campylomma livida , Capitophorus horni , Carneocephala fulgida , Cavelerius spp., Ceraplastes spp., Ceratovacuna lanigera , Ceroplastes ceriferus , Cerosipha gossypii , Chaetosiphon fragaefolii , Chionaspis tegalensis , Chlorita onukii , Chromaphis juglandicola , Chrysomphalus ficus , Cicadulina mbila , Cimex spp. , such as tropical bed bugs ( C. hemipterus ), temperate bed bugs ( C. lectularius ); Coccomytilus halli , Coccus spp., such as C. hesperidum , C. pseudognoliarum ; Corythucha arcuata , Creontiades dilutus , Cryptomyzus ribis , Chrysomphalus aonidum , Cryptom yzus ribis ), Ctenarytaina spatulata , Cyrtopeltis notatus , Dalbulus spp., Dasynus piperis , Dialeurodes spp. such as D. citrifolii ; Dalbulus maidis , Diaphorina spp.), such as D. citri ; Diaspis spp., such as D. bromeliae ; Dichelops furcatus , Diconocoris hewetti , Doralis spp., Dreyfusia nordmannianae ), Dreyfusia piceae , Drosicha spp.; Dysaphis spp., such as Dreyfusia picea , Dreyfusia spp . . pyri ), D. radicola ; Dysaulacorthum pseudosolani ; Dysdercus spp., such as D. cingulatus , D. intermedius ; Dysmicoccus spp. ), Edessa spp., Geocoris spp., Empoasca spp., such as broad bean leafhopper ( E. fabae ), Solana small green leaf butterfly ( E. solana ); Epidiaspis leperii , cotton aphid ( Eriosoma spp.), such as E. lanigerum , E. pyricola ; Leafhopper ( Erythroneura spp.); Eurygaster spp., such as wheat flat shield bug ( E. integriceps ); Blunt nose leafhopper ( Euscelis bilobatus ), Euschistus spp., such as soybean brown stink bug ( E. heroos ), tobacco bug ( E. impictiventris ), brown stinkbug ( E. servus ); Fiorinia theae , coffee ground mealybug ( Geococcus coffeae ), Glycaspis brimblecombei ; Halyomorpha spp., such as H. halys; Heliopeltis spp., Homalodisca vitripennis (=H. coagulata) ), Horcias nobilellus , Hyalopterus pruni , Hyperomyzus lactucae , Icerya spp., such as I. purchase ; Idiocerus spp., flat beak Idioscopus spp., Laodelphax striatellus , Lecanium spp., Lecanoideus floccissimus , Lepidosaphes spp., such as L. ulmi ; spp.), cotton red boll beak ( Leptoglossus phyllopus ), radish aphid ( Lipaphis erysimi ), Lygus spp., such as Lygus ( L. hesperus ), American pasture Lygus ( L. lineolaris ), L. pratensis ; Maconellicocus hirsutus , Marchalina hellenica , Macropes excavatus , Macrosiphum spp., such as M. rosae , wheat tube Aphid ( M. avenae ), Euphorbiae ( M. euphorbiae ); Macrosteles quadrilineatus , Mahanarva fimbriolata , Megacopta cribraria , Megoura viciae , Melanaphis pyrarius , sorghum aphid ( Melanaphis sacchari ); Melanocallis (=Tinocallis) caryaefoliae , Metcafiella spp., Metopolophium dirhodum , Monellia costalis , Monelliopsis pecanis ; Myzocallis coryli , Murgantia spp., Myzus spp. .), such as M. ascalonicus , M. cerasi, M. nicotianae , M. persicae , M. variants ; Aphids ( Nasonovia ribis-nigri ), Neotoxoptera formosana , Neomegalotomus spp , Nephotettix spp., such as N. malayanus , N. nigropictus , Leafhopper ( N. parvus ), Leafhopper ( N. virescens ) ; Nezara spp., such as N. viridula ; Brown rice lice ( Nilaparvata lugens ) , Nysius huttoni , Oebalus spp., such as O. pugnax ; Oncometopia spp., Orthezia praelonga , Oxycaraenus hyalinipennis , Parabemisia myricae , Parlatoria spp. , Parthenolecanium spp., such as P. corni , P. persicae ; Pemphigus spp., such as P. bursarius , P. populivenae ; Lice ( Perkinsiella saccharicida ), Phenacoccus spp., such as P. aceris , P. gossypii ; Phloeomyzus passerinii , Phorodon humuli , Phylloxera spp .), such as P. devastatrix ; Piesma quadrata , Piezodorus spp., such as P. guildinii ; Pinnaspis aspidistrae, Planococcus spp .), such as P. citri , P. ficus ; Prosapia bicincta , Protopulvinaria pyriformis, Psallus seriatus , Pseudacysta persea , Pseudaulacaspis pentagona , mealybug ( Pseudococcus spp.), such as P. comstocki ; Psylla spp., such as P. mali ; Pteromalus spp., Pulvinaria amygdali , Pyrilla spp ., Quadraspidiotus spp., such as Q. perniciosus ; Quesada gigas , Rastrococcus spp., Reduvius senilis , Rhizoecus americanus , Rhodnius spp., shallots Rhopalomyzus ascalonicus ; Rhopalosiphum spp., such as R. pseudobrassicas , R. inserttum , R. maidis , corn aphids Aphids ( R. padi ); Sagatodes spp., Cocoa brown Lygus ( Sahlbergella singularis ), Black Helmets ( Saissetia spp.), Sappaphis mala , Sappaphis mali , Scaptocoris spp . , grape leafhopper ( Scaphoides titanus ), wheat Schizaphis graminum , Schizoneura lanuginosa , Scotinophora spp., Selenaspidus articulatus , Sitobion avenae , Sogata spp., White-backed planthopper ( Sogatella furcifera ), Solubea insulatingis , Spissistilus festinus (=Stictocephala festina) , pear crown bug ( Stephanitis nashi ), Stephanitis pyrioides , Stephanitis takeyai , Tenalaphara malayensis , Tetraleurodes perseae , Therioaph is maculate , Thyanta spp., such as T . accerra , T. perditor ; Tibraca spp., Tomaspis spp., Toxoptera spp., such as T. aurantii ; Whitefly ( Trialeurodes spp.) , such as T. abutilonea , T. ricini , whitefly ( T. vaporariorum ); triatoma spp., trioza spp., small leafhopper (Typhlocyba spp . ), sharp shield scale Genus ( Unaspis spp.), such as U. citri , U. yanonensis ; and phylloxera ( Viteus vitifolii ); insects of the order Hymenoptera , such as Acanthomyops interjectus , Athalia rosae , Atta spp., such as A. capiguara , A. cephalotes, A. cephalotes , A. laevigata , A. robusta , A. sexdens , A. texana , Bombus spp. ), Brachymyrmex spp., Camponotus spp., such as C. floridanus , C. pennsylvanicus , C. modoc ; Cardiocondyla nuda , Chalibion sp . Crematogaster spp., Dasymutilla occidentalis , Diprion spp., Dolichovespula maculata , Dorymyrmex spp., Dryocosmus kuriphilus , Formica spp., Hoplocampa spp., Such as H. minuta , H. testudinea ; Iridomyrmex humilis , Lasius spp., such as L. niger , Linepithema humile , Liometopum spp., Leptocybe invasa , Monomorium spp., such as M. pharaonis , Monomorium , Nylandria fulva , Pachycondyla chinensis , Paratrechina longicornis , Paravespula spp., such as P. germanica , P. pennsylvanica , P. vulgaris ; Pheidole spp., such as brown ants ( P. megacephala ); Pogonomyrmex spp., such as red ants ( P. barbatus ), harvester ants ( P. californicus ), wasps ( Polistes rubiginosa ), Prenolepis impairs , Pseudomyrmex gracilis , Schelipron spp., Sirex cyaneus , Solenopsis spp., such as tropical fire ants ( S. geminata ), red fire ants ( S. invicta ), S. molesta , black fire ants ( S. richteri ), southern fire ants ( S. xyloni ); Sphecius speciosus , Sphex spp., Tapinoma spp., such as T. melanocephalum , T. sessile ; Tetramorium spp., such as T. caespitum , T. bicarinatum , Vespa spp., such as yellow-edged Wasps ( V. crabro ); Vespula spp., such as the hornet ( V. squamosal ); Wasmannia auropunctata , Xylocopa sp; Insects of the order Orthoptera, such as the house cricket ( Acheta domesticus ), Italian locust ( Calliptamus italicus ) , Chortoicetes terminifera , Ceuthophilus spp., Diastrammena asymamora , Dociostaurus maroccanus , Gryllotalpa spp., such as African mole cricket ( G. africana ), mole cricket ( G. gryllotalpa ); Gryllus spp., African sugarcane locust ( Hieroglyphus daganensis ), Indian yellow sandalwood locust ( Kraussaria angulifera ), migratory locust ( Locusta spp.), such as migratory locust ( L. migratoria ), brown locust ( L. pardalina ); black locust ( Melanoplus spp.), such as Two-striped black locust ( M. bivittatus ), red-footed black locust ( M. femurrubrum ), Mexican black locust ( M. mexicanus ), migratory black locust ( M. sanguinipes ), stone-dwelling black locust ( M. spretus ); stripes Red locust ( Nomadacris septemfasciata ), Senegalus senegalensis ( Oedaleus senegalensis ), Scapteriscus spp., Schistocerca spp., such as American desert locust ( S. americana ), desert locust ( S. gregaria ), Stemopelmatus spp. ., Tachycines aynamorus and Zonozerus variegatus ; Arachnida pests, such as Acari, such as Argasidae, Ixodidae and Sarcoptidae ), such as Amblyomma spp. (eg A. americanum , A. variegatum , A. maculatum ), Argas spp. .), such as A. persicu , Boophilus spp., such as B. annulatus , B. decoloratus , B. microplus ), Dermacentor spp., such as Dermacentor spp., such as D. silvarum, D. andersoni , D. variabilis , Hyalomma spp., such as Eye ticks ( H. truncatum ), Ixodes spp., such as I. ricinus , I. rubicundus , I. scapularis , Ixodes spp. Ixodes ( I. holocyclus ), Ixodes pacificus ( I. pacificus ), Rhipicephalus sanguineus , Ornithodorus spp., such as O. moubata , O. hermsi ), recurrent heat tick ( O. turicata ), Ornithonyssus bacoti , ear tick ( Otobius megnini ), chicken skin thorn mite ( Dermanyssus gallinae ), itchy mite ( Psoroptes spp.), such as sheep scabies ( P. ovis ), Rhipicephalus spp., such as R. sanguineus , R. appendiculatus , Rhipicephalus evertsi , root mite Rhizoglyphus spp., Sarcoptes spp., such as S. Scabiei ; and Eriophyidae, including Aceria spp., such as A. sheldoni , A. anthocoptes , Acallitus spp ., Aculops spp., such as A. lycopersici , A. pelekassi ; Aculus spp., such as A. schlechtendali ; Colomerus vitis , Jujube leaf rust mite ( Epitrimerus pyri ), orange wrinkled leaf gall mite ( Phyllocoptruta oleivora ); Eriophytes ribis and gall mite ( Eriophyes spp.), such as citrus gall mite ( Eriophyes sheldoni ); tarsonemidae (Tarsonemidae), Including Hemitarsonemus spp., Phytonemus pallidus and Polyphagotarsonemus latus , Stenotarsonemus spp., Steneotarsonemus spinki ; Tenuipalpidae, including short Brevipalpus spp., such as B. phoenicis ; Tetranychidae, including Eotetranychus spp., Eutetranychus spp., small-clawed Mites ( Oligonychus spp.), Petrobia latens , Tetranychus spp., such as cinnabar spider mite ( T. cinnabarinus ), T. evansi , Shenze spider mite ( T. kanzawai ), Pacific spider mite ( T, pacificus ), T. phaseulus , T. telarius and T. urticae ; Bryobia praetiosa ; Panonychus spp., such as P. ulmi , P. citri ; Metatetranychus spp. and Oligonychus spp., such as O. pratensis , O. perseae , Vasates lycopersici ; Raoiella indica , Carpoglyphidae , including Carpoglyphus spp.; Penthaleidae spp., such as Halotydeus destructor ; Demodicidae (Democidae) genus species, such as Demodex spp. ( Demodex spp.); Trombicidea, including chigger genus ( Trombicula spp.); Family Macronyssidae, including Ornothonyssus spp.; Pyemotidae, including Pyemotes tritici ; Tyrophagus putrescentiae ; Acaridae, including Acarus siro ; Araneida, such as Latrodectus mactans , Tegenaria agrestis , Chiracanthium sp , Lycosa sp Achaearanea tepidariorum and brown silk spider ( Loxosceles reclusa ); pests of the Phylum Nematoda, for example plant parasitic nematodes such as root-knot nematodes, Meloidogyne spp., such as northern Root-knot nematode ( M. hapla ), southern root-knot nematode ( M. incognita ), Javan root-knot nematode ( M. javanica ); cyst nematodes, Globodera spp., such as potato golden nematode ( G . rostochiensis ); Cyst nematodes ( Heterodera spp.), such as cereal cyst nematodes ( H. avenae ), soybean cyst nematodes ( H. glycines ), sugar beet cyst nematodes ( H. schachtii ), clover cyst nematodes ( H. trifolii ); seed gall nematodes, Anguina spp.; stem and leaf nematodes, Aphelenchoides spp., such as rice stem-point nematodes ( A. besseyi ); stinging nematodes, needle-stinging nematodes Nematodes of the genus Belonolaimus spp., such as B. longicaudatus ; pine nematodes, Bursaphelenchus spp., such as B. lignicolus , B. xylophilus ); Ringworms, Criconemella spp., Criconemella spp., such as C. xenoplax and C. ornata , and Criconemoides spp., such as Criconemoides informis , Criconemella spp. Genus ( Mesocriconema spp.); Bulb nematodes, Ditylenchus spp., such as D. destructor , D. dipsaci ; Trypanosoma, Dolichodorus spp.; Helicoidal nematodes, Heliocotylenchus multicinctus ; Heliocotylenchus multicinctus ; Sheath nematodes and sheath nematodes, Hemiccliophora spp. and Hemicriconemoides spp.; Hirshmanniella spp.; Hoploaimus spp.); pseudoroot-knot nematodes, Nacobbus spp.; needle nematodes, Longidorus spp., such as L. elongatus ; root-rot nematodes, Brachyphytes ( Pratylenchus spp.), such as P. brachyurus , P. neglectus , P. penetrans , P. curvitatus , P. goodeyi ); Perforator nematode, perforator nematode genus ( Radopholus spp .), such as banana perforator nematode ( R. similis ); Rhadopholus spp.; Rhodopholus spp.; R. robustus ), R. reniformis ; Scutellonema spp.; Root stump nematodes, Trichodorus spp. such as T. obtusus , T. primitivus ; Paratrichodorus spp., such as P. minor ; Stagnant nematodes, dwarf nematodes ( Tylenchorhynchus spp.), such as Clayton dwarf nematodes ( T. claytoni ), adventitious dwarf nematodes ( T. dubius ); citrus nematodes, Tylenchulus spp., such as T. semipenetrans ; sword nematodes, Xiphinema spp.; and other plant-parasitic nematode species; Isoptera (Isoptera) insects, for example yellow-necked wood termites ( Calotermes flavicollis ), Coptotermes spp., such as Taiwan milk termites ( C. formosanus ), C. gestroi , C. acinaciformis ; Cornitermes cumulans , Cryptotermes spp., such as C. brevis , C. cavifrons ; Globitermes sulfurus , Heterotermes spp., such as H. aureus , H. longiceps , H. tenuis ; Leucotermes flavipes , soil Termites ( Odontotermes spp. ), Incisitermes spp., such as I. minor , I. Snyder ; Marginitermes hubbardi , Mastotermes spp., such as M. darwiniensis , Neocapritermes spp., such as N. opacus , N. parvus ; Neotermes spp., Procornitermes spp., Zootermopsis spp., such as Z. angusticollis , Z. nevadensis , Reticulitermes spp., such as R. hesperus , R. tibialis , R. speratus , R. speratus ( R. flavipes ), R. grassei , European termite ( R. lucifugus ), R. santonensis , American small black termite ( R. virginicus ); Termes natalensis , Blattaria (Blattaria) insects, such as Blatta spp., such as B. orientalis, B. Lateralis ; Blattella spp., such as B. asahinae , B. germanica; Leucophaea maderae ; Panchlora nivea ; Periplaneta spp., such as American cockroach ( P. americana ), Australian cockroach ( P. australasiae ), brown cockroach ( P. brunnea ), black-breasted cockroach ( P. fuligginosa ), Japanese cockroach ( P. japonica ); Supella longipalpa ; Parcoblatta pennsylvanica; Eurycotis floridana; Pycnoscelus surinamensis , insects of the order Siphonoptera, such as Cediopsylla simples , Ceratophyllus spp., Ctenocephalides spp., such as C. felis , Ctenocephalides spp. C. canis , Xenopsylla cheopis , Pulex irritans, Trichodectes canis , Tunga penetrans and Nosopsyllus fasciatus , Thysanura ) Insects, such as Western silverfish ( Lepisma saccharina ), Ctenolepisma urbana and spotted fish ( Thermobia domestica ), Chilopoda (Chilopoda) pests, such as ground centipede ( Geophilus spp.); Scutigera (Scutigera spp.), Such as Scutigera coleoptrata , Diplopoda pests, such as Blaniulus guttulatus , Julus spp., Narceus spp., Symphyla pests, such as Scutigerella immaculata , Dermaptera insects, such as European ball fly ( Forficula auricularia ), insects of the order Collembola, for example Onychiurus ssp., such as Onychiurus armatus , pests of the order Isopoda, for example Armadillidium vulgare , Water lice ( Oniscus asellus ), Porcellio scaber , insects of the order Phthiraptera, for example Damalinia spp.; Pediculus spp., such as Pediculus humanus capitis , human lice ( Pediculus humanus corporis ), Pediculus humanus humanus ; pubic lice ( Pthirus pubis ); blood lice ( Haematopinus spp.), such as bovine blood lice ( Haematopinus eurysternus ), pig blood lice ( Haematopinus suis ); Linognathus spp.), such as Linognathus vituli ; Bovicola bovis , Menopon gallinae , Menacanthus stramineus and Solenopotes capillatus , Trichodectes spp .).

Examples of other pest species that can be controlled by compounds of formula (I) include Phylum Mollusca, Bivalvia, e.g. Dreissena spp.; Gastropoda, e.g. Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaeas spp. , Oncomelania spp., Pomacea canaliclata , Succinea spp.; Helminths, such as Ancylostoma duodenale , Ancylostoma ceylanicum , Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides , Ascaris spp. , Brugia malayi , Timor blue Brugia timori , Bunostomum spp ., Chabertia spp., Clonorchis spp ., Cooperia spp., Dicoela Dicrocoelium spp., Dictyocaulus filaria , Diphyllobothrium latum , Dracunculus medinensis , Echinococcus granulosus , Echinococcus multilocularis , Enterobius vermicularis , Faciola spp., Haemonchus spp. such as Haemonchus contortus ; Heterakis spp., Hymenolepis nana , Hyostrongulus spp., Loa Loa , Nematodirus spp., Nodules Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus , Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fueleborni, Strongyloides stercoralis , Stronyloides spp., Taenia saginata , Taenia saginata solium ), Trichinella spiralis , Trichinella nativa , Trichinella britovi , Trichinella nelsoni , Trichinella pseudopsiralis , Trichinella pseudopsiralis Trichostrongulus spp., Trichuris trichuria , Wuchereria bancrofti .

In one embodiment of the present invention, the harmful organisms are from the order Hemiptera, Lepidoptera, Coleoptera or Thysanoptera, preferably selected from the genus Whitefly, Leafhopper, Green Stinkbug, Aphid, Vicia faba Aphids, Tuxaphis, Helicopteris, Grassias, Sinella, Flower Weevil or Thrips (Orchid Thrips), more preferably Greenhouse Whitefly (Greenhouse Whitefly), Green Leafhopper (Two Black-tailed leafhopper ( Nephotettix virescens ) ) , rice brown planthopper ( B. persicae )), tobacco armyworm ( Heliothis virescens ), rice borer/strip borer- Chilo suppressalis , rice stem borer- tryporyza (=Scirpophaga) incertulas ) , cotton boll weevil (Cotton boll weevil ( Anthonomus grandis )) or thrips (Orchid thrips).

In one embodiment of the present invention, the present invention relates to a method of controlling rice harmful invertebrates in rice, the method comprising applying to said rice harmful invertebrates at least one non-racemic compound with pesticidal activity ( I) or its enantiomers or mixtures thereof.

In one embodiment of the present invention, the present invention relates to a method of controlling rice harmful invertebrates in rice, the method comprising administering to said rice harmful invertebrates at least one compound of formula I-R having enantiomeric excess (I) The pesticidally active compound or a mixture thereof.

In one embodiment of the present invention, the present invention relates to a method of controlling rice harmful invertebrates in rice, the method comprising applying to said rice harmful invertebrates at least one pesticidally active compound I-R or a mixture thereof.

Rice pests: In the context of the present invention, rice pest invertebrates are animal pests that occur in rice. Rice harmful invertebrates include insects, mites and nematodes, preferably insects. Known rice pest invertebrates in rice include, but are not limited to, the following species: Hemiptera: Brown planthopper - Brown rice hopper Sliverus striatellus - Spotted planthopper White-backed planthopper - White-backed planthopper Leafhopper - Leafhopper Leafhopper ( Cofana spectrum ) Green leafhopper - two-spotted black-tailed leafhopper, black-striped black-tailed leafhopper ( N. nigriceps ), black-tailed leafhopper ( N. cincticeps ), Malayan black-tailed leafhopper N. nigriceps Leafhopper ( Recilia dorsalis ) Corn Orange Leafhopper - Cicadulina bipunctata . acuta ) Rice brown bug - Nezara viridula , Pygomenida varipennis , Eysarcoris , Tibraca limbatriventris , Eysarcoris ventralis Small bug - Oebalus poecilus ), American rice bug ( Blissus leucopterus leucopterus ) rice mealybug, rice pink mealybug ( Brevennia rehi ), subcane mealybug ( Pseudococcus saccharicola ) rice aphid, red bellied tuber Aphids ( Rhopalosiphum rufiabdominalis ), wheat aphids ( Macrosiphum avenae ), armless aphids ( Hysteroneura setariae ), black-bellied four-veined aphids ( Tetraneuro nigriabdominalis ) bean root aphids - cotton root aphids ( Smynthurodes betae ) Lepidoptera: Rice bracts Insects - Parnara guttata , Melanitis Ieda ismene Rice borers/ Strip borers - Chilo borer, Chilo polychrusus , Chilo partellus , Chilo partellus ( Chilo plejadellus ) Rice stem borer - Chilotraea polychrysa Leaf insects- Rice leaf roller , Broad-grained wild borer ( Marasmia patnalis ), Rice striped wild-striped wild borer ( M. exigua ) Shaving insects/army insects- Oriental armyworm ( Pseudaletia separata ) Green caterpillars- Xanthodes transversa ( Xanthodes transversa ) Rice green caterpillar - Rice borer ( Narnaga aenescens ) Green horned caterpillar - Twilight butterfly, eyebrow eye butterfly ( Mycalesis sp ) Meadow armyworm - Spodoptera frugiperda Root cutter - Armyworm Rice Husk Worm - Nymphula depunctalis Black Caterpillar, Deer Moth ( Amata sp .) Long Hairy Caterpillar - Mocis frugalis Yellow Caterpillar, Psalis pennatula Rice Half Brown Inch moth, Pleurotus moth Pseudomonas oryzae, Golden double-spotted moth ( Chrysodeixis chalcites ) Grass moth - Rice leaf-cutting moth Cane borer - Small sugar cane borer Corn stalk borer - South American corn seedling borer Striped looper - South American hairy moth Europe Corn borer - corn borer ( Ostrinia nubilalis ) Mexican rice borer - Mexican rice borer Oryzophagus oryzae Rice iron beetle- Rice iron armor ( Diclodispa armigera ) Rice leaf beetle- Rice leaf beetle Rice black bug- Rice black bug ( Scotinophora vermidulate , S. vermidulate , S. lurida ), Broad-winged black bug ( S. latiuscula ) Rice flea beetle - Chaetocnima basalis maggot - Leucopholis irrorata, Leucopholis irrorata, Heteronychus sp , Bicho torito - Argentina Cyclopedia weevil - Cyclopsis genus Vitis brunnea - Colaspis brunnea, Louisiana beetle ( C. louisianae ) Rice pollen beetle, flower beetle ( Chilolaba acuta ) Diptera: stalks Flies - Chlorops oryzae ( Chlorops oryzae ) Liriomyza ( Agromyza oryzae ) Rice water fly / Rice straw fly - Hydrellia sasakii Rice water fly / Rice Liriomyzae - Rice water fly Leaf fly ( Hydrellia griseola ) Rice gall midge - Orseolia (= Pachydiplosis) oryzae Rice seedling fly - Rice awn fly ( Atherigona oryzae ) Rice midge - Chironomus cavazzai , Chironomus spp , Ring-footed midge Genus ( Cricotopus spp ) Thysanoptera: Rice thrips - rice thrips ( Chloethrips oryzae ), rice straight mane thrips ( Stenochaetothrips biformis ), naked thrips ( Perrisothrips sp. ), organ thrips ( Hoplothrips sp. ), Orthoptera: Rice Locust, Hieroglyphus banian , Hieroglyphus nigrorepletus , Catantops pinguis , Attractomorpha burri , Attractomorpha burri, A. crenulate ), willow grasshopper ( A. psittacina psittacina ), pointed grasshopper ( A. Bedeli ), toothless rice grasshopper ( Oxya adenttata ), Oxya ebneri , small rice grasshopper ( Oxya hyla intracata ), long-headed grasshopper ( Acrida turricata ) Locusts - Locusta migratoria manilensis mole crickets, African mole crickets ( Grylotalpa africana ) crickets: two-spotted crickets ( Gryllus bimaculatus ), black-headed brow crickets ( Teleogryllus occipitalis ), dexterous slender crickets ( Euscyrtus concinus ) katydids - Long-winged katydid ( Conocephalus longipennis ) Isoptera: Termites - Macrotermes gilvus , Syntermes molestans Hymenoptera: Ants - Tropical fire ants ( Solenopsis geminata ) Rice dry point nematodes - Leaf bud nematodes ( Aphelenchoides besseyi ) Ticks Acarid subclass: Rice ear mite - Steotarsonemus pinki ) Crustacea: Limulus - Triops longicaudatus , T. cancriformis Rice crayfish - Procambarus clarkii , Morris Green Crawfish ( Orconectes virilis ).

In addition, rice is affected by a series of bugs (including Leptocorisa chinensis , Lagynotomus elongates , Nerzara viridula , Eysacoris parvus , Oryza chinensis, Oryza americana Stinkbugs ( Oebalus pugnax ), Cletus trigonus ) and various mites, caterpillars, beetles, rootworms and maggots.

In one embodiment, the rice harmful invertebrate is a biting/chewing insect.

In one embodiment, the rice harmful invertebrate is a stinging/sucking insect.

In one embodiment, the rice harmful invertebrate is a file insect.

In one embodiment, the rice harmful invertebrate is a siphon insect.

In one embodiment, the rice harmful invertebrate is a sucking insect.

In one embodiment, the rice harmful invertebrates are selected from the group consisting of brown planthopper (BPH), brown planthopper (BPH), white-backed planthopper (White-backed planthopper), rice borer/strip borer (two Chilo borer), rice stem borer (Chilorrhizae three), rice leaf roller/leaf roller (rice leaf roller), rice weevil (rice water weevil).

In one embodiment, the rice harmful invertebrate is from the order Hemiptera or Lepidoptera.

In one embodiment, the rice harmful invertebrate is from the order Hemiptera. In another embodiment, the rice harmful invertebrate is a collembola, preferably selected from the group consisting of brown planthopper (BPH), brown planthopper (BPH), white-backed planthopper (white-backed planthopper), A. Cicada (Cicada bispots). In another embodiment, the harmful invertebrates for rice are selected from the group consisting of brown planthopper (BPH) and green leafhopper (Leafhopper bispott), preferably brown planthopper (BPH).

In one embodiment, the rice harmful invertebrate is the brown rice planthopper (BPH).

In one embodiment, the harmful invertebrate to rice is Leafhopper (Cicada bispott).

In another embodiment, the harmful invertebrates of rice are bedbugs, preferably selected from the group consisting of rice brown stinkbugs ( Oryza spp. , American rice bug).

In one embodiment, the rice harmful invertebrate is from the order Lepidoptera. In another embodiment, the rice harmful invertebrate is a stem borer, preferably a stem borer, preferably a rice borer (Chilobarer) or a rice stem borer (Chilobarer).

In another embodiment, the harmful invertebrates of rice are rice leaf rollers/leaf rollers (rice leaf rollers, rice borers, and rice borers).

In one embodiment, the rice harmful invertebrate is from the order Coleoptera. In another embodiment, the rice harmful invertebrate is the rice weevil (Rice weevil). In another embodiment, the rice harmful invertebrate is the rice weevil (oryza sativa).

In one embodiment, the rice harmful invertebrate is from the family Termitidae (Isoptera).

animal health The compounds and mixtures according to the invention are suitable for the treatment or protection of animals against parasitic infestation or infection. Accordingly, the present invention also relates to the use of the compounds according to the invention for the manufacture of a medicament for the treatment or protection of animals against parasitic infestation or infection. Furthermore, the invention relates to a method of treating or protecting animals against parasitic infestation and infection, which comprises administering or administering to the animal a parasiticidally effective amount of a compound of the invention orally, topically or parenterally.

The invention also relates to the non-therapeutic use of the compounds and mixtures of the invention for the treatment or protection of animals against parasitic infestation and infection. Furthermore, the invention relates to a non-therapeutic method of treating or protecting animals against parasitic infestation and infection, which comprises applying to the locus a parasiticidally effective amount of a compound of the invention.

The compounds and mixtures according to the invention are additionally suitable for combating or controlling parasites in and on animals. Furthermore, the invention relates to a method of combating or controlling parasites in and on animals, which comprises contacting the parasites with a parasiticidally effective amount of a compound of the invention.

The invention also relates to the non-therapeutic use of the compounds and mixtures according to the invention for controlling or combating parasites. Furthermore, the invention relates to a non-therapeutic method of combating or controlling parasites, which comprises applying to the locus a parasiticidally effective amount of a compound of the invention.

The compounds and mixtures of the invention can be effective by contact (via soil, glass, walls, mosquito nets, carpets, coverings or animal parts) and ingestion (eg baits). Furthermore, the compounds and mixtures of the invention can be administered at any and all stages of development.

The compounds and mixtures of the invention can be applied as such or in the form of compositions comprising the compounds and mixtures of the invention.

Compounds and mixtures of the present invention can also be mixed with compounds that act against pathogenic parasites, such as synthetic coccidiosis compounds; polyether antibiotics, such as Amprolium, Robenidin, Toltrazuril, Monensin, Salinomycin, Maduramicin, Lasalocid, Narasin, or Sedumycin Semduramicin; or with other mixed partners as defined above, or in the form of a composition comprising such mixtures.

The compounds and mixtures of the invention and compositions comprising them can be administered orally, parenterally or topically (eg transdermally). The compounds and mixtures of the present invention may be systemically or nonsystemically effective.

Administration can be performed prophylactically, therapeutically, or nontherapeutically. Furthermore, the application can be carried out prophylactically where the occurrence of parasites is expected.

As used herein, the term "contacting" includes direct contact (administering the compound/composition directly to the parasite, including or excluding direct application to the animal, such as the latter at its locus) and indirect contact (applying the compound/composition directly to the parasite) The composition is applied to the locus of the parasite). Contacting parasites by application to their locus is an example of a non-therapeutic use of the compounds and mixtures of the invention.

The term "locus" means the habitat, food supply, breeding ground, area, material or environment in which the parasite grows or can grow outside the body of an animal.

As used herein, the term "parasite" includes both endoparasites and ectoparasites. In some embodiments of the invention, internal parasites may be preferred. In other embodiments, ectoparasites may be preferred. Infections of warm-blooded animals and fish include but are not limited to lice, biting lice, ticks, nose flies, sheep ticks, biting flies, fruit flies, flies, myiasis larvae, chiggers, gnats, mosquitoes and fleas.

The compounds and mixtures of the present invention are especially useful against parasites of the following orders and species, respectively: Fleas (Flea orders), such as Ctenocephalus felis, Ctenocephalus canis, Ctenophora spp. Carnivorous fleas; cockroaches (Clattata), such as German cockroaches, Asian cockroaches, American cockroaches, Japanese cockroaches, brown cockroaches, black-breasted cockroaches, Australian cockroaches and oriental cockroaches; flies, mosquitoes (Diptera), such as Aedes aegypti, Aedes albopictus, Aedes harasser, Drosophila mexicani, Anopheles quinquefalis, Anopheles catastrophe, Anopheles albopedia, Anopheles gambiae, Anopheles fischeri, Anopheles albicans Anopheles, Anopheles minimus, Anopheles tetrapipes, Blowfly, Chrysomya hominivorax, Chrysomya hominivorax , Chrysomya hominivorax, Deerfly, Mothfly, Atlantic fly, Screwworm, Anthropophagus, Culicoides furious , Culex acutus, Aedes mosquito, Culex fatigue, Aedes vegetative, Veinless, Vein black, Human skin fly, Small hairy toilet fly, Horsefly, Glossia stinging fly, Glossina palpitations, Tsetse fly, Glue fly, Blood fly, Haplodiplosis equestris , Liriomyza, Dermatophagoides, Toddler midge, Lucilia caprina , Lucilia copper fly, Lucila sericata, Lycoria pectoralis , Mannia, Musca domestica, rot Fly, Sheep-nosed fly, Silver-footed sandfly, Columbian scaled mosquito, Psorophora discolor , Prosimulium mixtum , Red-tailed scorpion fly, Sarcophagus, band gnat, sting fly, Gadfly, North American black fly, Red horsefly and Dichaetes; lice (hair lice order), such as human head lice, human body lice, pubic lice, bovine blood lice, pig blood lice, calf lice, cattle lice, chicken lice, large chicken lice and buffalo blind lice; ticks and parasitic mites (Paramatites): Ticks (Ixodidae) such as Ixodes blacklegs, Ixodes pannata, Ixodes pacificus, Rhizocephalus sanguineus, Derma ticks, Derma ticks, Longstar ticks, Amblyomma maculata, Amblyomma herstii Marginal ticks, relapsing fever ticks and parasitic mites (Mesostigmata), e.g. Poultryalis spp. Acarapis spp. , Cheyletiella spp. , Ornithocheyletia spp. , Myobia spp. , Psorergates spp. , Demodex Genus, Chigger, Listrophorus spp. , Acarus spp. , Tyrophagus spp. , Caloglyphus spp. , Hypodectes spp. , Wing Pterolichus spp. , Itch mite, Chorioptes spp. , Otodectes spp . , Scabies, Notoedres spp. , Knee mite ( Knemidocoptes spp. ), Cytodites spp. and Laminosioptes spp ; bed bugs (Heteroptera): temperate bed bugs, tropical bed bugs, Reduvius senilis , triatomine bugs, red bugs genus, triatomine Stinkbugs ( Panstrongylus ssp ) and stinkbugs; lice orders, for example, Haemophilus spp., Glycerus spp., Phtirus spp. and Solenopotes spp.; Trichophagia (Arnblycerina and Ischnocerina suborders ), such as Trimenopon spp. , Menopon spp. , Trinoton spp. , Bovicola spp. , Werneckiella spp. , Lepikentron spp. , chewing lice Genus and Felicola spp.; Ascaris nematodes: whipworms and trichinellosis (Trichinella spp.), such as Trichinella ( Trichinella spp. ) , ( Trichidae ) Trichinella spp. ( Trichuris spp. ), Capillaria spp. ; Rod-shaped ones, such as Rhabditis spp. , Strongyloides spp. , Heliphalobus spp. ; From the order of the Nematodes, for example Strongylus spp. , Ancylostoma, Necator americanus , Upostomum ( hookworm ) , Trichostrongylus spp. , Haemonchus contortus , Oustia spp., Coopera spp., Leptocaulus spp., Dictyocaulus spp., Cyathostoma spp . , Nodularia spp., Stephanurus dentatus Ollulanus spp. , Chabertalus, crown nematodes, tracheal nematodes, Anticostomum spp., Uncinaria spp., Globocephalus spp. Necator spp. , Metastrongylus spp. , Muellerius capillaris , Protostrongylus spp. , Angiostrongylus spp. , Strongylus spp. Parelaphosstrongylus spp. , Aleurostrongylus abstrusus and Dioctophyma renale; Intestinal roundworms (Ascaris), such as Ascaris lumbricoides, Ascaris suum , Ascaridia galli , Parascaris equirum, Enterobius vermicularis ( pinworm ) , Toxocara canis , Toxascaris leonine , Skrjabinema spp. Oxyuris equi ; Cameliformes, such as Guinea worms (Guinea worms); Spirocerans, such as Thelazia spp. , Wuchereria spp. , Brugeria spp. ( Brugia spp. ), Onchocerca spp. , Dirofilari spp.a, Dipetalonema spp. , Setaria spp. , Elaeophora spp. , Spirocerca lupi and Habronema spp. , spiny-headed worms (Acanthocephala) such as Acanthocephalus spp. , Macracanthorhynchus hirudinaceus ) and Oncicola spp. , planarians (Platezoa): flukes (Trematodes), such as Faciola spp. , Fascioloides magna , Conglomerate ( Paragonimus spp. ), Dicrocoelium spp. , Fasciolopsis buski , Clonorchis sinensis , Schistosoma spp. , Trichobilharzia spp . ), winged flukes ( Alaria alata ), lung flukes ( Paragonimus spp. ) and Nanocyetes spp. ; Cercomeromorpha, especially tapeworms (tapeworms), such as Diphyllobothrium spp . Tenia spp. ), Echinococcus spp. , Dipylidium caninum , Multiceps spp. , Hymenolepis spp. Mesocestoides spp. ), Vampirolepis spp. , Moniezia spp. , Anoplocephala spp. , Sirometra spp. , Hymenolepis spp. .

As used herein, the term "animal" includes warm-blooded animals (including humans) and fish. Preferred are mammals such as cattle, sheep, pigs, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, buffaloes, donkeys, yellow deer and reindeer, and fur animals such as mink, chinchilla and Raccoons; birds such as hens, geese, turkeys and ducks; fish such as freshwater and saltwater fish such as trout, carp and eels. Especially preferred are domestic animals such as dogs or cats.

In general, "parasiticidally effective amount" means the amount required to achieve an observable effect on growth, including necrosis, death, arrest, prevention and removal, destruction or otherwise reducing the presence and activity of the target organism. required amount of active ingredient. The parasiticidally effective amount will vary for the various compounds/compositions used in the present invention. The parasiticidally effective amount of the composition will also vary depending on prevailing conditions, such as the desired parasiticidal effect and duration, target species, mode of application, and the like.

In general, it is advantageous to administer the compounds and mixtures according to the invention in a total amount of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day.

For oral administration to warm-blooded animals, the compounds and mixtures according to the invention may be formulated as animal feed, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, dips, gels, Tablets, boluses and capsules. In addition, the compounds and mixtures according to the invention can be administered to animals in their drinking water. For oral administration, the selected dosage form should provide the animal with 0.01 mg/kg to 100 mg/kg of the animal's body weight per day, preferably 0.5 mg/kg to 100 mg/kg of the animal's body weight per day.

Alternatively, the compounds (component I) and mixtures according to the invention can be administered to animals parenterally, for example by intrarumen, intramuscular, intravenous or subcutaneous injection. The compounds (component I) and mixtures according to the invention can be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compounds (component I) and mixtures according to the invention may be formulated as implants for subcutaneous administration. Alternatively, the Component I compounds may be administered to animals transdermally. For parenteral administration, the dosage form selected should provide the animal with 0.01 mg/kg to 100 mg/kg of the animal's body weight per day of the Component I compound.

The compounds (component I) and mixtures according to the invention can also be dipping solutions, dusts, powders, collars, medallions, sprays, shampoos, drip and pour-on formulations and Ointments or oil-in-water or water-in-oil emulsions are administered topically to animals. For topical application, dips and sprays generally contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm component I. In addition, the compounds (component I) and mixtures according to the invention can be formulated as ear tags for animals, especially quadrupeds, such as cattle and sheep.

Suitable formulations are: - solutions, such as oral solutions, concentrates diluted for oral administration, solutions for skin or body cavities, pour-on formulations, gels; - Emulsions and suspensions for oral or dermal administration; semisolid preparations; - formulations in which the active ingredient I or II or mixtures are processed in an ointment base or an oil-in-water or water-in-oil emulsion base; - solid preparations such as powders, premixes or concentrates, granules, pills, lozenges, boluses, capsules; aerosols and inhalants, and shaped articles containing the active compounds.

Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding other auxiliaries such as acids, bases, buffer salts, preservatives and solubilizers. Auxiliaries suitable for injection solutions are known in the art. The solution is filtered and filled aseptically.

Oral solutions are administered directly. Concentrates are administered orally after pre-diluted to the concentration to be used. Oral solutions and concentrates are prepared according to the state of the art and as described above for injectable solutions, without requiring sterile procedures.

Solutions for skin application are dripped, applied, smeared, sprayed or sprayed on. Solutions for application to the skin are prepared according to the state of the art and as described above for injection solutions without the need for sterile procedures.

The gel is applied or spread on the skin or introduced into a body cavity. Gels are prepared by treating solutions, which have been prepared as described for injection solutions, with sufficient thickening agent to yield a clear material with an ointment-like consistency. Suitable thickeners are known in the art.

The pour-on formulation is poured or sprayed on a limited area of the skin, the active compound I or mixture penetrates the skin and acts systemically. Pour-on formulations are prepared by dissolving, suspending or emulsifying the active ingredient I or II or a mixture in a suitable skin compatible solvent or solvent mixture. If appropriate, further auxiliaries are added, such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, binders. Suitable such auxiliaries are known in the art.

Emulsions can be administered orally, transdermally, or as injections. Emulsions are either water-in-oil or oil-in-water. It is prepared by dissolving the active ingredient I or the mixture in the hydrophobic or hydrophilic phase and homogenizing it with the solvent of the other phase by means of suitable emulsifiers and, if appropriate, other auxiliaries, which Auxiliaries such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-increasing substances. Suitable hydrophobic phases (oils), suitable hydrophilic phases, suitable emulsifiers and further auxiliaries suitable for emulsions are known in the art.

Suspensions can be administered orally or topically/transdermally. They are prepared by suspending the active ingredient I or II or the mixture in a suspending agent, adding, if appropriate, other auxiliaries, such as wetting agents, colorants, bioabsorption-promoting substances, preservatives, anti-oxidants, etc. Oxidizing agent, light stabilizer. Suitable suspending agents and other auxiliaries suitable for suspensions, including wetting agents, are known in the art.

Semisolid formulations can be administered orally or topically/transdermally. It differs from the aforementioned suspensions and emulsions only in its higher viscosity.

For the preparation of solid preparations, the active ingredient I or II or mixtures are admixed with suitable excipients, if appropriate with auxiliaries, and brought into the desired form. Adjuvants suitable for this purpose are known in the art.

Compositions useful in the present invention may generally comprise from about 0.001 to 95% of Component I of the present invention.

The ready-to-use preparation contains a compound acting against parasites, preferably ectoparasites, in a concentration of 10 ppm to 80% by weight, preferably 0.1 to 65% by weight, more preferably 1 to 50% by weight, most preferably 5 to 40% by weight %.

The preparation diluted before use contains the compound acting against ectoparasites in a concentration of 0.5 to 90% by weight, preferably 1 to 50% by weight.

In addition, the preparations contain a component I directed against endoparasites in a concentration of 10 ppm to 2% by weight, preferably 0.05 to 0.9% by weight, very preferably 0.005 to 0.25% by weight.

Topical application may be carried out with shaped articles containing the compound, such as loops, ornaments, ear tags, strips for fastening to body parts, adhesive tapes and foils.

It is generally advantageous to administer a solid formulation that releases a total of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg, optimally 25 mg/kg to 160 mg/kg over the course of three weeks. Compounds of the invention (component I) and mixtures in kg body weight of treated animals.

example Synthetic example: 3-(2-chlorothiazol-5-yl)-8-methyl-7-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidine-8 -onium-5-alkoxide (corresponding to compound I-1)

Step 1: 2-Chloro-N-methoxy-N-methyl-acetamide N-methoxymethylamine hydrochloride (345 g) and water (1.5 L) were cooled to 0°C. To this reaction mixture was added _K2CO3 (1466 g) in portions, followed by methyl tert-butyl ether (1000 mL) at 0 ° _C . The reaction mixture was cooled to -5 °C. Chloroacetyl chloride (400 g) in methyl tert-butyl ether (500 ml) was added dropwise at -5°C to 0°C, and stirred at 0°C for 2 hours. The reaction mixture was brought to 20-25°C. The desired product was obtained from the organic layer as a white solid (438 g, 90% yield; 98.45% HPLC purity).

Step 2: 2-Chloro-1-(2-chlorothiazol-5-yl)ethanone Under nitrogen atmosphere, 2-chlorothiazole (187 ml) in 750 ml tetrahydrofuran was cooled to -20°C. Isopropylmagnesium chloride x LiCl (1684 ml, 1.3 mol in THF) was added dropwise and stirred at -20°C for 60 minutes. A solution of 2-chloro-N-methoxy-N-methyl-acetamide (250 g) in tetrahydrofuran was added dropwise at -20°C to -25°C. The reaction mixture was stirred at -20°C for 90 minutes. Saturated aqueous ammonium chloride solution was added at -20°C, then the reaction mixture was brought to 20-25°C. The two phases were separated and the aqueous phase was extracted with ethyl acetate. The desired crude product was obtained as a dark brown oil from the combined organic layers, which was treated with methyl tert-butyl ether containing charcoal and silica to give the crude product as a light brown oil (335 g), used directly in the next step.

Step 3: N-[2-chloro-1-(2-chlorothiazol-5-yl)ethylidene]-2-methyl-propane-2-sulfinamide at 20-25°C under nitrogen atmosphere Next, to the crude material 2-chloro-1-(2-chlorothiazol-5-yl)ethanone (335 g) in THF was added tert-butylsulfinamide (206 g) and Ti(OEt) ₄ (396ml). The mixture was heated to 50°C and stirred for 2 hours, then cooled to 20-25°C and diluted with ethyl acetate. After adding water, the mixture was stirred for 30 minutes, then filtered. The organic phase was evaporated to obtain the desired crude product as a brown oil. After treatment with methyl tert-butyl ether containing activated charcoal and silica, the crude product (365 g) was obtained as a light brown oil which was used directly in the next step.

Step 4: N-[2-Chloro-1-(2-chlorothiazol-5-yl)ethyl]-2-methyl-propane-2-sulfinamide was added to N-[ Add NaBH ₄ (23 g) and stirred for 30 minutes. A saturated aqueous ammonium chloride solution was added at 0 °C. The organic layer yielded the desired crude product (310 g) as a brown oil after extraction with ethyl acetate.

Step 5: 2-Chloro-1-(2-chlorothiazol-5-yl)ethanamine hydrochloride At 20-25°C, mix N-[2-chloro-1-(2-chlorothiazol-5-yl)ethyl]-2-methyl-propane-2-sulfinamide with methanol containing HCl ( 1 mol, 620 mL) were stirred together for 12 hours. Methanol was removed under vacuum to give a light yellow sticky solid (244 g), which was washed with methyl tert-butyl ether and then ethyl acetate to give a light yellow solid (78 g, 26 % yield, >98% purity).

Step 6: 4-(2-Chlorothiazol-5-yl)-N-methyl-thiazolidine-2-imine At 23°C, 2-chloro-1-(2-chlorothiazol-5-yl)ethylamine hydrochloride (285 g) in methyl tert-butyl ether and 2 molar NaOH aqueous solution (1060 mL) Stir for 20 minutes. The organic layer yielded the free amine (230 g) as a light brown oil.

The amine (230 g) in ethanol was reacted with triethylamine NEt3 (351 ml) and Me-NCS (143.2 g) at 22 to 25°C for 18 hours. The reaction mass was concentrated to obtain a brown residue, to which aqueous NaOH (114 g in 920 mL of water) was added. The resulting mixture was heated to 100°C for 2 hours, then cooled to 20-25°C and diluted with water. After extraction with ethyl acetate, the organic layer yielded crude 4-(2-chlorothiazol-5-yl)-N-methyl-thiazolidine-2-imine (256 g) as a brown solid, which was mixed with 20% ethyl acetate in heptane (300 mL) was stirred together for 30 minutes. After filtration, the product was obtained as a brown solid (245 g, 85% yield).

Step 7: 3-(2-Chlorothiazol-5-yl)-8-methyl-7-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidine-8 -Onium-5-alkoxide (I-1) 4-(2-Chlorothiazol-5-yl)-N-methyl-thiazolidine-2-imine (110 g) in toluene was stirred at 110 to 115°C. After addition of bis(4-chlorophenyl)-2-phenylmalonate (226 g), the reaction mixture was stirred at this temperature for 2 hours and then cooled to 40 to 45°C. After removing the toluene under vacuum, a brown solid was obtained which was triturated with methyl tert-butyl ether to obtain a yellow solid.

Stirring in methyl tert-butyl ether (1 L) at 22 to 25 °C for 14 hours yielded a pale yellow solid (160 g). Further purification by dissolution in dichloromethane and precipitation with methyl tert-butyl ether gave the desired product (129 g, 80% yield) as a fine light yellow powder. *: HPLC method: retention time (minutes); mass-to-charge ratio m/z HPLC Method A: MSD4/5: Shimadzu Nexera UHPLC + Shimadzu LCMS 20-20, ESI Column: Phenomenex Kinetex 1.7µm XB-C18 100A, 50 × 2.1mm Mobile phase: A: water + 0.1% trifluoroacetic acid; B: acetonitrile, temperature: 60°C Gradient: 5% B to 100% B in 1.50min; 100% B 0,25min Flow rate: 0.8 ml/min to 1.0 ml/min in 1.51 min MS method: ESI positive, mass range (m/z): 100-700 HPLC Method B: MSD4/5: Shimadzu Nexera UHPLC + Shimadzu LCMS 20-20, ESI Column: Agilent Eclipse Plus C18, 50mm × 4.6mm × 3 Mobile phase: A = 10 mM ammonium formate (0.1% formic acid), B = acetonitrile (0.1% formic acid), flow rate = 1.2 ml/min. Column oven: 30°C Gradient: = 10% B to 100% B - 1.5min, hold 1min, 2.51min - 10% B; run time = 3.50 min HPLC Method C: Same as method A, but MS method: ESI positive, mass range (m/z): 100-1400

Example - separation of enantiomers: R-3-(2-chlorothiazol-5-yl)-8-methyl-7-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidine-8- Onium-5-alkoxide and S-3-(2-chlorothiazol-5-yl)-8-methyl-7-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidine-8- Onium-5-alkoxide

3-(2-chlorothiazol-5-yl)-8-methyl-7-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidine-8 of Example 1 The enantiomers of the -onium-5-alkoxides can be separated by preparative chiral supercritical fluid chromatography. 126 g of rac-3-(2-chlorothiazol-5-yl)-8-methyl-7-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidine were isolated -8-ium-5-alkoxide. This resulted in 53.4 g of R-3-(2-chlorothiazol-5-yl)-8-methyl-7-oxo-6-phenyl-2,3-dihydrothiazolo[ 3,2-a]pyrimidin-8-ium-5-alkoxide and 57.7 g of S-3-(2-chlorothiazol-5-yl)-8-methyl-7-oxo at a retention time of 1.41 min -6-Phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidin-8-ium-5-olate. For these residence times, refer to the analysis methods listed below. The configuration of the chiral centers was determined by X-ray analysis.

Analytical Separation Method: Instrument: Thar Analytical SFC Column: Chiralpak AS-H, 150×4.6 mm id, 5 u Mobile Phase: A is CO ₂ and B is MeOH, Gradient: B%=40% Flow Rate: 4.0 mL/min, back pressure: 100 bar, column temperature: 35°C wavelength: 220 nm

Preparative Separation Method: Instrument: Thar 80 Preparative SFC Column: Chiralcel OJ-H, 250×30 mm ID 5 u Mobile Phase: A is CO ₂ and B is CH ₃ CN, Gradient: B% = 50% Flow Rate : 80 g/min, Back pressure: 100 bar, Column temperature: 40°C Wavelength: 220 nm Cycle time: 6.5 min Sample preparation: Dissolve racemic substance in MeOH-CH ₃ CN-DCM (1:1:0.5 ) to 20 mg/mL, and filtered through a membrane with a pore size of 0.45 um. Injection: 4 mL per injection.

After separation, the fractions were dried via a rotary evaporator at a bath temperature of 35°C to yield the two enantiomers.

Preparation of compounds of formula I with enantiomeric excess: Characterization can be by coupled high performance liquid chromatography/mass spectrometry (HPLC/MS), gas chromatography (GC), by NMR or by their melting point to proceed. HPLC method: Agilent Eclipse Plus C18, 150mm×4.6mm ID×5um gradient A=0.1% TFA/water, B=0.1% TFA/acetonitrile. Flow rate = 1.4 ml/min., Column oven temperature = 30°C Gradient program = 10% B - 100% B - 5min, hold 2min, 3min - 10% B. Run time = 10 min LCMS method 1: C18 column (50 mm × 3.0 mm × 3µ) Gradient A = 10 Mm ammonium formate/water, B = 0.1% formic acid/acetonitrile Flow rate = 1.2 ml/min., column oven temperature = 40°C Gradient program = 10% B to 100% B in 1.5 min, hold 1 min 100% B, 1 min - 10% B Run time: 3.75 min Chiral HPLC method 1: ChiralPak IA column, 150 mm ×4.6 mm× 5µ Mobile phase A=heptane, B=isopropanol, flow rate=1.0 ml/min, column oven temperature=40℃, gradient program=10% B isocratic; running time: 20 min for chiral HPLC Method 3: ChiralPak IA column, 150 mm×4.6 mm×5µ mobile phase A=heptane, B=isopropanol, flow rate=1.0 ml/min, column oven temperature=40℃, gradient program=40% B isocratic ; run time: 20 min ¹ H-NMR: signal is characterized by chemical shift (ppm) relative to tetramethylsilane, its multiplicity and its integral (given relative number of hydrogen atoms). The following abbreviations are used to characterize the multiplicity of signals: m = multiplet, q = quartet, t = triplet, d = doublet and s = singlet.

The abbreviations used are: h for hours, min for minutes, rt for residence time and ambient temperature for 20-25°C.

Example 1: Preparation of compound IR-1 with enantiomeric excess ((3 R )-3-(2-chlorothiazol-5-yl)-8-methyl-7-oxo-6-phenyl- 2,3-Dihydrothiazolo[3,2-a]pyrimidin-4-ium-5-alkoxide) compound of formula I-1: Step 1: Preparation of 2-chloro-N-methoxy-N-methoxy Base-Acetamide:

N-methoxymethylamine hydrochloride (345 g), water (1.6 liters), and The resulting reaction mixture was cooled to 0 to -5°C. Potassium carbonate (1466 g) was then added portionwise to the above reaction mixture followed by methyl tert-butyl ether (1.4 L). Chloroacetyl chloride (400 g) was dissolved in tert-butyl methyl ether (0.2 L) and added dropwise to the above kept reaction mixture at -5°C to 0°C, and the reaction mixture was stirred at 0°C 2 hours. The reaction mixture was allowed to reach ambient temperature and the two phases were separated. The organic layer was dried over sodium sulfate, filtered and evaporated to give 2-chloro-N-methoxy-N-methyl-acetamide as a white solid (440 g, 90% yield, HPLC purity 98.0 area %).

Step 2: Preparation of 2-chloro-1-(2-chlorothiazol-5-yl)ketene: Into a 5 L four-necked flask equipped with a Teflon blade stirrer, reflux condenser, and heat pack was fed 2-chlorothiazole (250 g), THF (0.75 L), and the resulting reaction mixture was cooled to 0 to - 5°C. Isopropylmagnesium chloride lithium chloride (1.929 L, 1.3 M solution in THF) was then added to the above held reaction mixture at 0 to -5 °C over 0.5 h. The reaction mixture was then heated to 40°C and the reaction was continued at 40°C for 2 hours. Chloro-(2-chloro-(2- Formation of chlorothiazol-5-yl)magnesium species. The reaction mixture was cooled to 0 to -5 °C, and a solution of 2-chloro-N-methoxy-N-methyl-acetamide (343 g) in THF (0.25 L) was added dropwise. The reaction was continued for 1 hour at -5 to 0°C, and the progress of the reaction was monitored by HPLC. The reaction mixture was quenched with 1.5 N aqueous HCl (1 L) at -5 to 0 °C and then warmed to ambient temperature. The two phases were separated and the aqueous phase was extracted with methyl tert-butyl ether (2 x 300 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated to give a crude residue. The crude product was dissolved in methyl tert-butyl ether (0.7 L) at ambient temperature, and activated carbon (4 g) and silica (80 g, 60-120 mesh) were added. The slurry was stirred for 0.5 h, filtered through a Buchner funnel and washed with methyl tert-butyl ether (0.3 L). The filtrate was evaporated to obtain 2-chloro-1-(2-chlorothiazol-5-yl)ethanone (409 g, HPLC purity 46 area %) as a light brown oil.

Step 3: Preparation of [2-(2-chlorothiazol-5-yl)-2-oxo-ethyl] acetate: At ambient temperature, the 2 - Chloro - 1- ( 2 - chlorothiazol - 5 - yl ) ethanone (15 g, HPLC purity 46 area%) and dimethylformamide (45 mL) were fed into a 0.25 L three-necked flask . Sodium acetate (12.55 g) was then added in portions and the reaction was continued for 4 hours at ambient temperature. The progress of the reaction was monitored by HPLC (conversion >95% by HPLC). The reaction was quenched with water (50 mL) and extracted with methyl tert-butyl ether (3 x 100 mL). The two phases were separated and the combined organic phases were dried over sodium sulfate, filtered and evaporated to give a crude residue (17 g). The crude product was purified by silica gel column chromatography to obtain [ 2- ( 2 - chlorothiazol - 5 - yl ) -2 - oxo - ethyl ] acetate (7.5 g) as a yellow solid .

Step 4: Preparation of 1-(2-chlorothiazol-5-yl)-2-hydroxy-ethanone: Into a 250 mL three-necked flask equipped with a magnetic stirrer, reflux condenser and thermal pack was fed acetic acid [ 2 − ( 2 - Chlorothiazol - 5 - yl ) -2 - oxo - ethyl ] ester (7.5 g) and 1 N HCl in MeOH (50 mL). The resulting solution was stirred for 5 hours and the progress of the reaction was monitored by TLC. The methanol in the reaction mixture was distilled in vacuo, and the resulting crude residue was purified by column chromatography to obtain 1- ( 2 - chlorothiazol - 5 - yl ) -2 - hydroxy - ethanone (2.8 g , HPLC purity of 84 area%).

Step 5: Preparation of 4-(2-chlorothiazol-5-yl)-5H-oxathiazole 2,2-dioxide Feed into a 100 mL three-necked flask equipped with a magnetic stirrer, reflux condenser and heat pack 1- ( 2 - chlorothiazol - 5 - yl ) -2 - hydroxy - ethanone (1 g), toluene (20 mL), chlorosulfamide (0.975 g) and p-toluenesulfonic acid (0.214 g). The resulting solution was heated to 100°C and stirred for 1 hour. Reaction progress (>95% conversion) was monitored by HPLC. The reaction mixture was quenched with water and extracted with MTBE (15 mL x 2). The two phases were separated, the organic phase was evaporated and 4- ( 2 - chlorothiazol - 5 - yl ) -5H - oxathiazole 2,2 - dioxide (0.42 g) was purified by column chromatography .

Step 6: Preparation of (4R)-4-(2-chlorothiazol-5-yl)oxathiazolidine 2,2-dioxide a) Preparation of rhodium catalyst - RhCl[(R,R)-TsDPEN]Cp*:

Under a nitrogen atmosphere, [RhCl ₂ Cp*] ₂ (2.0 g), (1R, 2R)-N-pair Tosyl-1,2-diphenylethylenediamine (2.38 g), dichloromethane (68 mL) and triethylamine (1.72 ml). The resulting slurry was stirred at 22-27 °C for 0.5 h, and distilled water (40 mL) was added. The two phases were separated and the organic phase was washed with water (40 mL). The organic phase was dried over sodium sulfate, filtered and evaporated to give a brown solid residue. The brown residue was triturated with n-heptane (20 mL), filtered and dried under nitrogen to afford RhCl[(R,R)-TsDPEN]Cp* (3.4 g) as a red solid.

b) Preparation of HCOOH-NEt ₃ mixture: In a 2 liter 3 neck round bottom flask was added formic acid (275 mL, >= 99% w/w) and cooled to 0 °C. At 0°C, triethylamine 250 mL, >=99% w/w) was slowly added thereto and used for the reaction immediately.

c) Preparation of (4R)-4-(2-chlorothiazol-5-yl)oxathiazolidine 2,2-dioxide: Into a 100 ml two-necked flask equipped with a magnetic stirrer, condenser and heat pack Feed in 4- ( 2 - chlorothiazol - 5 - yl ) -5H - oxthiazole 2,2 - dioxide (0.5 g) and dimethylformamide (15 mL, 30 V ) , degas with nitrogen for 10 minute. RhCl[( R , R )-TsDPEN]Cp* (27 mg) was then added followed by dropwise addition of HCOOH-NEt ₃ (2.5 mL, ratio 5:2). The resulting mixture was stirred for 2 hours. HPLC showed >97% conversion. The reaction mixture was quenched with water (15 ml) and extracted with methyl tert-butyl ether (3 x 50 mL). The combined organic phases were evaporated to obtain ( 4R ) -4- ( 2 - chlorothiazol - 5 - yl ) oxathiazolidine 2,2 - dioxide ( 500 mg; 90 area% HPLC purity (rt=3.645 min.) , >99% ee, for chiral HPLC method 1).

Step 7: Preparation of (4R)-4-(2-Chlorothiazol-5-yl)-N-methyl-thiazolidine-2-imine (4R)-4-(2-chlorothiazol-5-yl)oxathiazolidine 2,2-dioxide (0.5 g, 99% ee), ethanol (2 ml ), methyl isothiocyanate (0.228 g) and triethylamine (0.56 ml). The resulting mixture was stirred at 22-27°C for 14 hours. Organic volatiles were then removed in vacuo, and sodium hydroxide (0.2 g) and water (2 mL) were added to the reaction flask. The reaction mixture was heated to 100 °C and stirred for 2 hours. The reaction was diluted with water (2 mL) and extracted with methyl tert-butyl ether (2 x 50 mL). The organic phase was dried over sodium sulfate and evaporated in vacuo to give (4R)-4-(2-chlorothiazol- 5 - yl ) -N - methyl - thiazolidine - 2 - imine as a brown oil [0.34 g, m / z = 234 amu (M+H ⁺ )].

Step 8: Preparation of (3R)-3-(2-chlorothiazol-5-yl)-8-methyl-7-oxo-6-phenyl-2,3-dihydrothiazolo[3,2- a] Pyrimidin-4-ium-5-alkoxide: Under nitrogen atmosphere, feed ( E , 4R ) -4- ( 2 -chlorothiazol - 5 - yl ) -N - methyl - thiazolidine - 2 - imine (0.34 g ), toluene (2 mL) and heated to 110 °C. Then bis ( 2,4,6 - trichlorophenyl ) -2 - phenylmalonate ( 0.857 g) was added in portions to the reaction mass kept at 110 ° C . After stirring at 110°C for 2 hours, HPLC showed >99% conversion. The reaction was cooled below 50 °C, the precipitated light yellow solid was filtered through a sintered funnel, and the solid residue was washed with methyl tert-butyl ether (4 mL) and dried in vacuo to give ( 3R )- 3 -( 2 - Chlorothiazol - 5 - yl ) -8 - methyl - 7 - oxo - 6 - phenyl - 2,3 - dihydrothiazolo [ 3,2 - a ] pyrimidin - 4 - ium - 5 - alkoxide ( _ _ _ 110 mg, m / z = 378 amu (M+H ⁺ ) and 95.2% enantiomeric excess, chiral HPLC method 3). ¹ H NMR (300 MHz, DMSO-d6): 3.42(s, 3H), 3.94(d, J=12 Hz, 1H), 4.25-4.32(m, 1H), 6.48 (d, J=8.1 Hz, 1H ), 7.06-7.11(m, 1H), 7.21-7.26(m, 2H), 7.6(d, J= 7.5 Hz, 1H), 7.96(s, 1H).

biological instance If not stated otherwise, the test solutions were prepared as follows:

The active compound is dissolved at the desired concentration in a 1:1 (vol:vol) mixture of distilled water:acetone. Test solutions were prepared on the day of use.

Test compound I-R-1 used in the following biological examples was in 95% enantiomeric excess unless otherwise specified.

Test compound I-S-1 used in the following biological examples was in 95% enantiomeric excess unless otherwise specified.

B.1 Rice green leafhopper (two-spotted leafhopper): Clean and wash the rice seedlings 24 hours before spraying. The active compounds were formulated in 50:50 acetone:water (v:v) with the addition of 0.1% v/v surfactant (EL 620). Potted rice seedlings were sprayed with 5 ml of the test solution, air-dried, placed in cages and inoculated with 10 adults. The treated rice plants are maintained at about 28-29°C and about 50-60% relative humidity. The percent mortality was recorded after 72 hours.

B.2 Rice brown planthopper (Rice brown planthopper): Clean and wash the rice seedlings 24 hours before spraying. The active compounds were formulated in 50:50 acetone:water (v:v) with the addition of 0.1% v/v surfactant (EL 620). Potted rice seedlings were sprayed with 5 ml of the test solution, air-dried, placed in cages and inoculated with 10 adults. The treated rice plants are maintained at about 28-29°C and about 50-60% relative humidity. The percent mortality was recorded after 72 hours.

B.3 Cowpea aphid (Alfalfa aphid): To assess control of cowpea aphids via contact or systemic means, the test unit consisted of 24-well microtiter plates containing broad bean leaf discs.

Compounds were formulated using solutions containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the leaf discs at 2.5 µl using a custom-made micro-atomizer in two replicates.

After application, the leaf discs were air-dried and 5-8 adult aphids were placed on the leaf discs within the wells of the microtiter plate. Aphids were then allowed to suck the treated leaf discs and incubated for 5 days at about 23±1°C and about 50±5% relative humidity. Aphid mortality and fecundity were then assessed visually.

B.4 Thrips (Orchid Thrips): Adult orchid thrips for bioanalysis were obtained from colonies maintained continuously under laboratory conditions. For testing purposes, test compounds were diluted in a 1:1 mixture of acetone:water (v:v) plus 0.01% v/v Alkamuls ^® EL 620 surfactant.

The thrips efficacy of each compound was assessed by using the flower dip technique. Plastic Petri dishes were used as test sites. All petals of individual whole orchids were dipped in the treatment solution and allowed to dry. The treated flowers were placed in individual petri dishes along with approximately 20 adult thrips. The Petri dish is then covered with a lid. During the analysis period, all test sites were kept under continuous light and a temperature of about 28°C. After 3 days, on each flower, the number of live thrips was counted along the inner wall of each Petri dish. The percent mortality was recorded 72 hours after treatment.

Table A below shows the event data: Table A :

B.3. Rice borers B.3a Vial Bioanalysis

Straw collected in the field was washed with tap water and cut to a certain length. Straws were air-dried and then placed individually in vials (=repeated, 3 times). Approximately 125 μl of test solution was sprayed per vial. The treated straw in the vial was air-dried under a laboratory fume hood. After air-drying, each straw was inoculated with 10 newborn (0-day-old) borer larvae. The vial is then capped. Devices were kept in a storage room maintained at 27°C and 65% RH for three days. Three days after inoculation, straws were manually dissected for larval mortality assessment. The data (Table C) show activity against two rice stem borers. Table C: Efficacy of neutral ionic compounds against rice borer

B.3b Foliar spraying All three pots (=repeats) of four- to five-week-old potted rice per treatment were simultaneously sprayed with 12 mL of the test solution. After spray application, the plants were air-dried in the laboratory before inoculation. After air-drying, 5- to 6-day-old CHILSU egg masses were used for inoculation. One day after inoculation, all borer-infested potted rice plants were transferred to the screening chamber until final evaluation. Evaluations were performed 10 days after treatment and inoculation. Whole plant damage was assessed for tiller dissection prior to cutting each mound at the base. Each dissected tiller was inspected for dead (if possible) and surviving stem borer larvae.

The results showed that the tested compounds had excellent activity against the rice stem borer in terms of larval mortality and feeding inhibition Table D: Efficacy of neutral ionic compounds against rice stem borer by foliar spraying

B.3c Water application The test solution was poured onto the soil of each potted rice plant (=repeat), five tillers per pot. After water application, the treated plants were transferred to the screening room for three days, followed by borer inoculation in the laboratory. Three days after the water application, 5- to 6-day-old CHILSU egg masses were used for inoculation. One day after inoculation, all borer-infested potted rice plants were transferred to the screening chamber until final evaluation. Evaluations were performed 12 days after treatment (9 days after inoculation). Whole plant damage was assessed for tiller dissection prior to cutting each mound at the base. Each dissected tiller was inspected for dead (if possible) and surviving stem borer larvae.

The data (Table 3) show that all tested compounds against the rice stem borer obtained similar results in terms of larval mortality and feeding inhibition by water application compared to foliar application. Table E: Effect of neutral ionic compounds on rice strips by irrigation The effect of moth

Example of a mixture: Synergy can be described as an interaction in which the combined effect of two or more compounds is greater than the sum of the individual effects of each compound. The presence of synergy between two mixed partners (X and Y) in terms of percentage control can be calculated using the Colby equation (Colby, SR, 1967, Calculating Synergistic and Antagonistic Responses in Herbicide Combinations, Weeds , 15, 20-22):

A combined effect is synergistic when the observed combined control effect is greater than the expected combined control effect (E).

The following tests demonstrate the control efficacy of the compounds, mixtures or compositions of the present invention against specified pests, where Compound I-R-1 is in 95% enantiomeric excess unless otherwise specified. However, the pest control protection provided by the compounds, mixtures or compositions is not limited to these species. In some cases, it was found that combinations of compounds of the present invention and other invertebrate pest control compounds or agents exhibit synergistic effects against certain important invertebrate pests.

Analysis using the Colby equation to determine synergy or antagonism between mixtures or compositions.

test 1 To assess control of P. vicia fabae via contact or systemic means, the test unit consisted of 24-well microtiter plates containing leaf discs of vicia faba.

Compounds or mixtures were formulated using solutions containing 75% water and 25% DMSO. Various concentrations of formulated compounds or mixtures were sprayed onto leaf discs at 2.5 µl in two replicates using a custom-made micro-atomizer.

For the experimental mixtures in these tests, equal volumes of each of the two mixing partners were mixed together at the desired concentrations.

After application, the leaf discs were air-dried and 5-8 adult aphids were placed on the leaf discs within the wells of the microtiter plate. Aphids were then allowed to suck the treated leaf discs and incubated for 5 days at 23±1°C, 50±5% RH. Aphid mortality and fecundity were then assessed visually. The results are listed in Table 1 for the mixtures tested. Table 1: IR-1 and Cinot.

test 2 To assess control of green peach aphid via a systemic approach, the test unit consisted of a 96-well microtiter plate containing liquid artificial feed under an artificial membrane.

Compounds or mixtures were formulated using solutions containing 75% water and 25% DMSO. Various concentrations of formulated compounds or mixtures were pipetted into aphid feed in duplicate using custom-made pipettes.

For the experimental mixtures in these tests, equal volumes of each of the two mixing partners were mixed together at the desired concentrations.

表2.2：I-R-1及氟芬隆.

表2.3：I-R-1及三氟苯嘧啶.

表2.4：I-R-1及因得克.

表2.5：I-R-1及氟啶蟲醯胺.

表2.6：I-R-1及α-賽滅寧.

After application, 5-8 adult aphids were placed on the artificial membrane in the wells of the microtiter plate. Aphids were then allowed to suck the treated aphid feed and incubated for 3 days at 23±1 °C, 50±5% RH. Aphid mortality and fecundity were then assessed visually. The results are listed in Tables 2.1 to 2.6 for the mixtures tested. Table 2.1: IR-1 and Spinosad.

Table 2.2: IR-1 and Flufenoron.

Table 2.3: IR-1 and trifluoropyrimidine.

Table 2.4: IR-1 and Indec.

Table 2.5: IR-1 and floxamid.

Table 2.6: IR-1 and α-Saphenin.

test 3 To assess control of boll weevil, the test unit consisted of a 24-well microtiter plate containing insect diet and 20-30 boll weevil eggs.

Compounds or mixtures were formulated using solutions containing 75% water and 25% DMSO. 20 µl of various concentrations of formulated compounds or mixtures were sprayed onto insect diets using a custom-made micro-atomizer in duplicate.

For the experimental mixtures in these tests, equal volumes of each of the two mixing partners were mixed together at the desired concentrations.

表3.2：I-R-1及賜諾特.

表3.3：I-R-1及氟唑醯胺.

After application, the microtiter plates were incubated for 5 days at 23±1°C, 50±5% RH. Egg and larval mortality was then assessed visually. The results are listed in Tables 3.1 to 3.3 for the mixtures tested. Table 3.1: IR-1 and Flufenoron.

Table 3.2: IR-1 and Cinot.

Table 3.3: IR-1 and Fluazolamide.

test 4 To assess control of tobacco armyworm (N. tabaci moth), the test unit consisted of a 96-well microtiter plate containing an insect diet and 15-25 N. tabaci moth eggs.

Compounds or mixtures were formulated using solutions containing 75% water and 25% DMSO. 10 µl of various concentrations of formulated compounds or mixtures were sprayed onto insect diets using a custom-made micro-atomizer in duplicate.

For the experimental mixtures in these tests, equal volumes of each of the two mixing partners were mixed together at the desired concentrations.

表4.2：I-R-1及α-賽滅寧.

After application, the microtiter plates were incubated for 5 days at 28±1°C, 80±5% RH. Egg and larval mortality was then assessed visually. The results are presented in Tables 4.1 and 4.2 for the mixtures tested. Table 4.1: IR-1 and Pemetrazine.

Table 4.2: IR-1 and α-Saphenin.

test 5 To evaluate control of whitefly in a greenhouse, the test unit consisted of a 96-well microtiter plate containing leaf discs of eggplant with whitefly eggs. Compounds or mixtures were formulated using solutions containing 75% water and 25% DMSO. Various concentrations of formulated compounds or mixtures were sprayed onto insect diets at 2.5 µl using a custom-made micro-atomizer in duplicate.

For the experimental mixtures in these tests, equal volumes of each of the two mixing partners were mixed together at the desired concentrations.

After application, the microtiter plates were incubated for 6 days at 23±1°C, 65±5% RH. Mortality of hatched reptiles was then assessed visually. The results are listed in Table 5 for the mixtures tested. Table 5: IR-1 and oxazoxafil.

表6.2：I-R-1及賜諾特.

Test 6: For evaluating the control of the brown planthopper (BPH) by foliar spraying. Clean potted rice seedlings properly marked for upper leaf cutting. Three potted rice plants per treatment concentration/combination were placed on top of a rotating disc (270 mm) and sprayed with 12 mL of spray solution. The treated plants were allowed to air dry in the laboratory for about one hour. After air drying, each treated rice plant was covered. Each treated plant was infested with N. lugens using suction vacuum. Plants were maintained in a holding room at 27°C±1°C, 50±5% RH and 24 hours of light. Seven days after infestation, percent mortality was recorded by counting dead and surviving N. lugens on plants and in water. The average controls after 7 days for the compounds and mixtures tested are given in Tables 6.1 to 6.2. Table 6.1: IR-1 and Pemetrazine.

Table 6.2: IR-1 and Cinot.

Test 7: To assess control of P. vicia fabae via contact or systemic means, the test unit consisted of 24-well microtiter plates containing leaf discs of vicia faba.

Compounds or mixtures were formulated using solutions containing 75% water and 25% DMSO. Various concentrations of formulated compounds or mixtures were sprayed onto leaf discs at 2.5 µl in two replicates using a custom-made micro-atomizer.

For the experimental mixtures in these tests, equal volumes of each of the two mixing partners were mixed together at the desired concentrations.

表7.2：

After application, the leaf discs were air-dried and 5-8 adult aphids were placed on the leaf discs within the wells of the microtiter plate. Aphids were then allowed to suck the treated leaf discs and incubated for 5 days at 23±1°C, 50±5% RH. Aphid mortality and fecundity were then assessed visually. The results are presented in Tables 7.1 and 7.2 for the mixtures tested. Table 7.1:

Table 7.2:

Test 8: To assess control of green peach aphid via a systemic approach, the test unit consisted of a 96-well microtiter plate containing liquid artificial feed under an artificial membrane.

Compounds or mixtures were formulated using solutions containing 75% water and 25% DMSO. Various concentrations of formulated compounds or mixtures were pipetted into aphid feed in duplicate using custom-made pipettes.

For the experimental mixtures in these tests, equal volumes of each of the two mixing partners were mixed together at the desired concentrations.

表8.2：

After application, 5-8 adult aphids were placed on the artificial membrane in the wells of the microtiter plate. Aphids were then allowed to suck the treated aphid feed and incubated for 3 days at 23±1 °C, 50±5% RH. Aphid mortality and fecundity were then assessed visually. The results are presented in Tables 8.1 and 8.2 for the mixtures tested. Table 8.1:

Table 8.2:

Test 9: To assess control of boll weevil, the test unit consisted of a 24-well microtiter plate containing insect diet and 20-30 boll weevil eggs.

Compounds or mixtures were formulated using solutions containing 75% water and 25% DMSO. 20 µl of various concentrations of formulated compounds or mixtures were sprayed onto insect diets using a custom-made micro-atomizer in duplicate.

For the experimental mixtures in these tests, equal volumes of each of the two mixing partners were mixed together at the desired concentrations.

表9.2：

After application, the microtiter plates were incubated for 5 days at 23±1°C, 50±5% RH. Egg and larval mortality was then assessed visually. The results are presented in Tables 9.1 and 9.2 for the mixtures tested. Table 9.1:

Table 9.2:

Test 10: To assess control of tobacco armyworm (N. tabaci moth), the test unit consisted of a 96-well microtiter plate containing an insect diet and 15-25 N. tabaci moth eggs.

Compounds or mixtures were formulated using solutions containing 75% water and 25% DMSO. Different concentrations of formulated compounds or mixtures were sprayed onto the insect feed at 10 µl using a custom-made micro-atomizer in duplicate.

For the experimental mixtures in these tests, equal volumes of each of the two mixing partners were mixed together at the desired concentrations.

表10.2：

After application, the microtiter plates were incubated for 5 days at 28±1°C, 80±5% RH. Egg and larval mortality was then assessed visually. The results are presented in Tables 10.1 and 10.2 for the mixtures tested. Table 10.1:

Table 10.2:

Test 11: To evaluate control of whitefly in a greenhouse, the test unit consisted of a 96-well microtiter plate containing leaf discs of eggplant with whitefly eggs. Compounds or mixtures were formulated using solutions containing 75% water and 25% DMSO. Different concentrations of formulated compounds or mixtures were sprayed onto the insect feed at 2.5 µl using a custom-made micro-atomizer in duplicate.

For the experimental mixtures in these tests, equal volumes of each of the two mixing partners were mixed together at the desired concentrations.

表11.2：

After application, the microtiter plates were incubated for 6 days at 23±1°C, 65±5% RH. Mortality of hatched reptiles was then assessed visually. The results are presented in Tables 11.1 and 11.2 for the mixtures tested. Table 11.1:

Table 11.2:

Test 12: To assess control of the yellow fever mosquito (Aedes aegypti), the test unit consisted of a 96-well microtiter plate containing 200 µl of tap water and 5-15 newly hatched Aedes aegypti larvae per well.

Compounds or mixtures were formulated using solutions containing 75% water and 25% DMSO. Different concentrations of formulated compounds or mixtures were sprayed onto the insect feed at 2.5 µl using a custom-made micro-atomizer in duplicate.

For the experimental mixtures in these tests, equal volumes of each of the two mixing partners were mixed together at the desired concentrations.

After application, the microtiter plates were incubated at 28±1°C, 80±5% RH for 2 days. Larval mortality was then assessed visually. The results are listed in Table 12 for the mixtures tested. Table 12:

Claims (11)

A compound of formula IR-1 or a salt thereof,

A pesticidal mixture comprising (1) a compound of formula IR-1 or a salt thereof as defined in claim 1, and (2) at least one compound II selected from the following group: M.1 acetylcholine Esterase (AChE) inhibitors: M.1A carbamates; or M.1B organophosphates; M.2. GABA-gated chloride channel antagonists: M.2A cyclodiene organochlorine compounds; or M.2B Phenylpyrazoles (fiproles) (phenylpyrazoles); M.3 M.3A Sodium channel modulators of pyrethroids; or M.3B Sodium channel modulators; M.4 Nicotine Acetylcholine receptor agonist (nAChR): M.4A neonicotinoids; or compound M.4A.1 4,5-dihydro-N-nitro-1-(2-cyclo Oxyethylmethyl)-1H-imidazol-2-amine, M.4A.2: (2E-)-1-[(6-chloropyridin-3-yl)methyl]-N'-nitro- 2-Pentylidene carboxamidine, or M4.A.3: 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1, 2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine; or M.4B Nicotine; M.4C Sulfoxaflor; M.4D Fluoropyrfuranone ( flupyradifurone); M.4E triflumezopyrim; M.5 nicotinic acetylcholine receptor ectopic activators: spinosyns; M.6 avermectins Chloride channel activators of milbemycins; M.7 juvenile hormone mimics; M.8 various non-specific (multi-site) inhibitors; M.9 TRPV channel modulators of stringed instruments; M.10 Mite growth inhibitor; M.12 Mitochondrial ATP synthase inhibitor; M.13 Oxidative phosphorylation decoupler via disruption of proton gradient; M.14 Nicotinic acetylcholine receptor (nAChR) channel Blocker; M.15 Inhibitor of chitin biosynthesis type 0; M.16 Inhibitor of chitin biosynthesis type 1; M.17 Diptera insect molting disruptor; M.18 Ecdysone receptor stimulator M.19 Octopamine receptor agonists; M.20 Mitochondrial complex III electron transport inhibitors; M.21 Mitochondrial complex I electron transport inhibitors; M.22 Voltage-dependent sodium channel inhibitors M.23 Inhibitor of Acetyl CoA Carboxylase; M.24 Mitochondrial Complex IV Electron Transport Inhibitor; M.25 Mitochondrial Complex II Electron Transport Inhibitor; M.28 Diamide Similar to ryanodine receptor modulators, M.28.1: (R)-3-chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1- (Trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamide, M.28.2: (S)-3-chloro- N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonium Acylethyl)phthalamide, M.28.3: Cyclaniliprole or M.28.4: Methyl-2-[3,5-dibromo-2-({[3-bromo -1-(3-Chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-dimethylcarbazinate; or M.28.5a )N-[4,6-dichloro-2-[(diethyl-λ-4-sulfenyl)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)- 5-(Trifluoromethyl)pyrazole-3-carboxamide; M.28.5b) N-[4-chloro-2-[(diethyl-λ-4-sulfide)aminoformyl] -6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M.28.5c)N-[4- Chloro-2-[(di-2-propyl-λ-4-sulfide)aminoformyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5 -(trifluoromethyl)pyrazole-3-carboxamide; M.28.5d) N-[4,6-dichloro-2-[(di-2-propyl-λ-4-sulfide) Carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M.28.5h)N-[4, 6-Dibromo-2-[(diethyl-λ-4-sulfide)aminoformyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoroform Base) pyrazole-3-carboxamide; M.28.5i) N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methyl Phenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide; M.28.5j) 3-chloro-1-(3-chloro-2- Pyridyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide ; M.28.5k) 3-bromo-N-[2,4-dichloro-6-(methylaminoformyl)phenyl]-1-(3,5-dichloro-2-pyridyl)- 1H-pyrazole-5-carboxamide; M.28.5l) N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl ]-1-(3-chloro-2-pyridyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide; or M.28.6: cyhalodiamide; or M.29: Chord modulators - undefined target site; M.UN. Insecticidally active compounds with unknown or unclear mode of action; M.UN.3: 11-(4-chloro-2,6- Dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11-en-10-one; M.UN.4:3- (4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one, M. UN.5: 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H -1,2,4-Triazol-5-amine, or an active agent based on bacillus firmus (Votivo, I-1582); M.UN.6: Flupyrimin; M.UN .8: Fluazaindolizine; M.UN.9.a): 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-iso Oxazol-3-yl]-2-methyl-N-(1-oxothietane-3-yl)benzamide; M.UN.9.b): Fluazolamide ( fluxametamide); M.UN.10: 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole; M.UN.11.b) 3-(Benzoylmethylamino)-N-[2-bromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoro Methyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluoro-benzamide; M.UN.11.c) 3-(benzoylmethylamino)-2- Fluoro-N-[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-benzoyl Amine; M.UN.11.d) N-[3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6- (Trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.11.e)N-[3-[[[2-bromo-4- [1,2,2,2-Tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]-2-fluoro-phenyl]-4 -Fluoro-N-methyl-benzamide; M.UN.11.f) 4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1,2,2, 2-Tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.UN .11.g) 3-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl] -6-(Trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.11.h) 2-Chloro-N-[3-[[ [2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl] -3-Pyridinecarboxamide; M.UN.11.i) 4-cyano-N-[2-cyano-5-[[2,6-dibromo-4-[1,2,2,3 ,3,3-Hexafluoro-1-(trifluoromethyl)propyl]phenyl]aminoformyl]phenyl]-2-methyl-benzamide; M.UN.11.j)4 -cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3, 3-Hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide; M.UN.11.k) N-[5-[[2-chloro-6- Cyano-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]aminoformyl]-2-cyano-phenyl]- 4-cyano-2-methyl-benzamide; M.UN.11.l) N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro- 1-Hydroxy-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M. UN.11.m) N-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl] phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.UN.11.n) 4-cyano-N-[2 -Cyano-5-[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl base]phenyl]-2-methyl-benzamide; M.UN.11.o) 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4- [1,2,2,2-Tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]aminoformyl]phenyl]-2-methyl-benzamide; M.UN.11 .p) N-[5-[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl ]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; or M.UN.12.a) 2-(1,3-dioxane-2 -yl)-6-[2-(3-pyridyl)-5-thiazolyl]-pyridine; M.UN.12.b) 2-[6-[2-(5-fluoro-3-pyridyl) -5-thiazolyl]-2-pyridyl]-pyrimidine; M.UN.12.c) 2-[6-[2-(3-pyridyl)-5-thiazolyl]-2-pyridyl]- Pyrimidine; M.UN.12.d) N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; M.UN.12.e ) N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; M.UN.12.f) N-ethyl-N-[ 4-Methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propionamide; M.UN.12.g) N-methyl-N-[4-methyl -2-(3-Pyridyl)thiazol-5-yl]-3-methylthio-propionamide; M.UN.12.h)N,2-Dimethyl-N-[4-methyl- 2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propionamide; M.UN.12.i) N-ethyl-2-methyl-N-[4-methyl -2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propionamide; M.UN.12.j) N-[4-chloro-2-(3-pyridyl)thiazole -5-yl]-N-ethyl-2-methyl-3-methylthio-propionamide; M.UN.12.k) N-[4-chloro-2-(3-pyridyl)thiazole -5-yl]-N,2-dimethyl-3-methylthio-propionamide; M.UN.12.l) N-[4-chloro-2-(3-pyridyl)thiazole-5 -yl]-N-methyl-3-methylthio-propionamide; M.UN.12.m) N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N -Ethyl-3-methylthio-propionamide; M.UN.14a) 1-[(6-chloro-3-pyridyl)methyl]-1,2,3,5,6,7-hexa Hydrogen-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine; or M.UN.14b) 1-[(6-chloropyridin-3-yl)methyl Base]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol; M.UN.16a)1- Isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.UN.16b) 1-(1,2-dimethylpropyl) -N-ethyl-5-methyl-N-pyridazine-4-yl-pyrazole-4-carboxamide; M.UN.16c) N,5-dimethyl-N-pyridazine-4- Base-1-(2,2,2-trifluoro-1-methyl-ethyl)pyrazole-4-carboxamide; M.UN.16d)1-[1-(1-cyanocyclopropyl ) ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-formamide; M.UN.16e) N-ethyl-1-(2-fluoro -1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16f) 1-(1,2-dimethylpropane Base) -N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16g) 1-[1-(1-cyanocyclopropyl) ethyl Base]-N,5-Dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16h) N-methyl-1-(2-fluoro-1-methyl M.UN.16i) 1-(4,4-difluorocyclohexyl)-N- Ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.UN.16j) 1-(4,4-difluorocyclohexyl)-N,5- Dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide, M.UN.17a) N-(1-methylethyl)-2-(3-pyridyl)-2H- Indazole-4-carboxamide; M.UN.17b) N-cyclopropyl-2-(3-pyridyl)-2H-indazole-4-carboxamide; M.UN.17c) N-ring Hexyl-2-(3-pyridyl)-2H-indazole-4-carboxamide; M.UN.17d) 2-(3-pyridyl)-N-(2,2,2-trifluoroethyl )-2H-indazole-4-carboxamide; M.UN.17e) 2-(3-pyridyl)-N-[(tetrahydro-2-furyl)methyl]-2H-indazole-5 -Formamide; M.UN.17f) methyl 2-[[2-(3-pyridyl)-2H-indazol-5-yl]carbonyl]hydrazine carboxylate; M.UN.17g)N-[( 2,2-difluorocyclopropyl)methyl]-2-(3-pyridyl)-2H-indazole-5-carboxamide; M.UN.17h)N-(2,2-difluoropropane Base)-2-(3-pyridyl)-2H-indazole-5-carboxamide; M.UN.17i) 2-(3-pyridyl)-N-(2-pyrimidinylmethyl)-2H -Indazole-5-carboxamide; M.UN.17j) N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridyl)-2H-indazole-5 -Formamide, M.UN.18a) N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoro Propylthio)acrylamide; M.UN.18b) N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3, 3-trifluoropropylsulfinyl)propionamide; M.UN.18c)N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[(2, 2-Difluorocyclopropyl)methylthio]-N-ethyl-acrylamide; M.UN.18d)N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl ]-3-[(2,2-difluorocyclopropyl)methylsulfinyl]-N-ethyl-acrylamide; M.UN.19 Salolaner (sarolaner); M.UN. 20 Lotilaner (lotilaner); M.UN.21 N-[4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1, 1,2,2,2-Pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide; M.UN.22a 2-(3-Ethylsulfonyl- 2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, or M.UN.22b 2-[3-ethylsulfonyl-5-( Trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine; M.UN.23a 4-[5-(3,5 -Dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxazolidine-4 -yl]-2-methyl-benzamide, or M.UN.23b 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)- 4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidine-4-yl]-2-methyl-benzamide; M .UN.24a) N-[4-chloro-3-(cyclopropylaminoformyl)phenyl]-2-methyl-5-(1,1,2,2,2-pentafluoroethyl) -4-(trifluoromethyl)pyrazole-3-formamide or M.UN.24b) N-[4-chloro-3-[(1-cyanocyclopropyl)aminoformyl]phenyl ]-2-Methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide; M.UN.25 Ainopa Rui (acynonapyr); M.UN.26 benzpyrimoxan (benzpyrimoxan); M.UN.27 2-chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl- 5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide; M.29.28 Oxa oxazosulfyl; A) Inhibitors of complex III of the respiratory inhibitor Qo site: azoxystrobin (A.1.1), coumethoxystrobin (A.1.2), syringae coumoxystrobin (A.1.3), dimoxystrobin (dimoxystrobin) (A.1.4), enestroburin (enestroburin) (A.1.5), fenaminstrobin (A.1.6), bacteria Fenoxystrobin/flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), Mandalorian ice (mandestrobin) (A.1.10), metominostrobin (A.1.11), orysastrobin (A.1.12), picoxystrobin (A.1.13), becclomin (pyraclostrobin) (A.1.14), pyraclostrobin (pyrametostrobin) (A.1.15), pyraoxystrobin (pyraoxystrobin) (A.1.16), trifluorosensitive (trifluoxystrobin) (A.1.17), 2(2- (3-(2,6-dichlorophenyl)-1-methyl-allylaminooxymethyl)-phenyl)-2methoxyimino-N methyl-acetamide (A .1.18), pyribencarb (A.1.19), triclopyricarb/chlorodincarb (A.1.20), famoxadone (A.1.21) , Fenamidone (A.1.21), methyl-N-[2-[(1,4-dimethyl-5phenyl-pyrazol-3-yl)oxymethyl]phenyl] -N-methoxy-carbamate (A.1.22), 1-[3-chloro-2[[1(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl ]phenyl]-4-methyl-tetrazol-5-one (A.1.23), 1-[3-bromo-2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxygen Base methyl] phenyl] -4-methyl-tetrazol-5-one (A.1.24), 1-[2-[[1-(4-chlorophenyl) pyrazol-3-yl] oxy Methyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one (A.1.25), 1-[2-[[1-(4-chlorophenyl)pyrazole-3 -yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one (A.1.26), 1-[2-[[1-(2,4-dichloro Phenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one (A.1.27), 1-[3-cyclopropyl- 2-[[2-Methyl-4(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4methyl-tetrazol-5-one (A.1.30), 1[ 3(Difluoromethoxy)-2-[[2-methyl-4-(1methylpyrazol-3yl)phenoxy]methyl]phenyl]-4methyl-tetrazole-5- Ketone (A.1.31), 1-methyl-4-[3-methyl-2[[2methyl-4-(1-methylpyrazol-3yl)phenoxy]methyl]phenyl] Tetrazol-5-one (A.1.32), (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxyl-2-methoxyimine Base-N,3-dimethyl-pent-3-enamide (A.1.34), (Z,2E)5[1(4-chlorophenyl)pyrazol-3-yl]oxy-2- Methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.35), pyriminostrobin (A.1.36), pyrflustrobin (bifujunzhi) (A.1.37 ), 2-(o-((2,5-dimethylphenyl-oxy-methylene)phenyl)-3-methoxy-methyl acrylate (A.1.38); complexation of Qi sites Inhibitors of substance III: cyazofamid (A.2.1), amisulbrom (A.2.2), [(6S,7R,8R) 2-methylpropionic acid 8 benzyl -3-[(3-Hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxononyl-7 -yl] esters (A.2.3), fenpicoxamid (A.2.4); complex II inhibitors: benodanil (A.3.1), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A. .3.6), fluopyram (A.3.7), fudolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.11), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), Penflufen (A.3.15), Penthiopyrad (A.3.16), Pydiflumetofen (A.3.17), Pyreflumide Pyraziflumid (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21), 3 ( Difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4 carboxamide (A.3.22), 3(trifluoromethyl) -1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4 formamide (A.3.23), 1,3-dimethyl-N-(1 , 1,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.24), 3-(trifluoromethyl)-1,5 dimethyl-N-(1, 1,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.25), 1,3,5-trimethyl-N-(1,1,3-trimethyl Indan-4-yl)pyrazole-4-carboxamide (A.3.26), 3-(difluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindene Full-4-yl)pyrazole-4-carboxamide (A.3.27), 3-(difluoromethyl)-N(7 fluoro-1,1,3-trimethyl-indan-4-yl )-1-methyl-pyrazole-4-carboxamide (A.3.28), N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-5- Fluoro-1,3-dimethyl-pyrazole-4-carboxamide (A.3.29), (E)-2-[2-[(5-cyano-2-methyl-phenoxy)methanol Base] phenyl] -3-methoxy-prop-2-enoic acid methyl ester (A.3.30), N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropane Base-3-(difluoromethyl)-5 fluoro-1-methyl-pyrazole-4-carboxamide (A.3.31), 2-(difluoromethyl)-N-(1,1,3 -Trimethyl-indan-4-yl)pyridine-3-formamide (A.3.32), 2-(difluoromethyl)-N-[(3R)-1,1,3-trimethyl Indan-4-yl]pyridine-3-carboxamide (A.3.33), 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4- Base) pyridine-3-carboxamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl ] Pyridine-3-carboxamide (A.3.35), 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3- Formamide (A.3.36), 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl]pyridine-3-methyl Amide (A.3.37), 2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A .3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethyl-indan-4 base]pyridine-3-carboxamide (A. 3.39); other respiratory inhibitors: diflumetorim (A.4.1); nitrophenyl derivatives: binapacryl (A.4.2), dinobuton (A.4.3), Dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone (A.4.7); organometallic compounds : fentin salts; ametoctradin (A.4.11); silthiofam (A.4.12); B) sterol biosynthesis inhibitors (SBI fungicides) C14 demethylase inhibitors: triazoles: azaconazole (B.1.1), bitertanol (B.1.2), bromu-conazole (B.1.3), Cyproconazole (B.1.4), difenoconazole (B.1.5), diniconazole (B.1.6), diniconazole-M (B.1.7), Epsil Epoxiconazole (B.1.8), Fenbuconazole (B.1.9), Fluquinconazole (B.1.10), Flusilazole (B.1.11), and Fenbuconazole (B.1.11) flutriafol) (B.1.12), Fickley (hexaconazole) (B.1.13), imibenconazole (B.1.14), ipconazole (B.1.15), metconazole (B.1.15) .1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazole (B.1.20), penconazole (B.1.21), Pukeli (propiconazole) (B.1.22), prothioconazole (B.1.23), simeconazole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon (B.1.27), triadimenol (B.1.28), triticonazole (B.1.29), uniconazole (B.1.30 ), ipfentrifluconazole (B.1.37), mefentrifluconazole (B.1.38), 2-(chloromethyl)-2-methyl-5-(p-tolylmethyl) base)-1(1,2,4-triazol-1-ylmethyl)cyclopentanol (B.1.43); imidazoles: imazalil (B.1.44), pefurazoate (B.1.45), prochloraz (B.1.46), triflumizol (B.1.47); pyrimidines, pyridines and piperazines: fenarimol (B.1.49 ), bifenox (pyrifenox) (B.1.50), saifoning (triforine) (B.1.51), [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-two Fluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol (B.1.52); δ14-reductase inhibitors: adimorph (aldimorph) (B.2.1), mobendazim (dodemorph ) (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (fenpropidin) (B.2.6), piperalin (B.2.7), spiroxamine (B.2.8); 3-keto reductase inhibitors: fenhexamid ) (B.3.1); Other sterol biosynthesis inhibitors: chlorphenomizole (B.4.1); C) Nucleic acid synthesis inhibitors phenylamide or acyl amino acid fungicides: Benzox benalaxyl (C.1.1), metalaxyl benalaxyl (benalaxyl-M) (C.1.2), fine benalaxyl (kiralaxyl) (C.1.3), metalaxyl (metalaxyl) (C.1.4 ), high-efficiency metalaxyl (metalaxyl-M) (C.1.5), furamide (ofurace) (C.1.6), oxadixyl (C.1.7); other nucleic acid synthesis inhibitors: Shawenning (hymexazole) (C.2.1), octhilinone (octhilinone) (C.2.2), oxolinic acid (oxolinic acid) (C.2.3), bupirimate (C.2.4), 5-fluoro Cytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidine-4amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidine- 4 amine (C.2.7), 5-fluoro-2 (4 chlorophenylmethoxy) pyrimidine-4 amine (C.2.8); D) cell division and cytoskeleton inhibitors tubulin inhibitors: Mianlaide (benomyl) (D.1.1), carbendazim (D.1.2), fuberidazole (D1.3), thiabendazole (D.1.4), thiophanate methyl (thiophanate -methyl)(D.1.5), 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine (D.1.6), 3-chloro-6- Methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine (D.1.7), N-ethyl-2-[(3-ethynyl-8-methyl-6- Quinolinyl)oxy]butanamide (D.1.8), N-ethyl-2-[(3-ethynyl-8methyl-6quinolyl)oxy]-2-methylthio- Acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolin-yl)oxy]-N(2-fluoroethyl)butyramide (D.1.10) , 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methoxy-acetamide (D.1.11), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-propyl-butyramide (D.1.12), 2-[(3-ethynyl-8-methyl Base-6-quinolyl)oxy]-2-methoxy-N-propyl-acetamide (D.1.13), 2-[(3-ethynyl-8-methyl-6-quinoline Base) oxy]-2-methylthio-N-propyl-acetamide (D.1.14), 2[(3 ethynyl-8-methyl-6-quinolyl)oxy]-N -(2-fluoroethyl)-2-methylsulfanyl-acetamide (D.1.15), 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro -phenyl)-2,5-dimethyl-pyrazol-3amine (D.1.16); other cell division inhibitors: diethofencarb (D.2.1), ethaboxam (D. .2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6 ), pyriofenone (D.2.7); E) amino acid and protein synthesis inhibitors methionine synthesis inhibitors: cyprodinil (E.1.1), mepanipyrim (mepanipyrim ) (E.1.2), pyrimethanil (pyrimethanil) (E.1.3); protein synthesis inhibitors: blasticidin-S (blasticidin-S) (E.2.1), kasugamycin (E. .2.2), kasugamycin hydrochloride hydrate (E.2.3), midiomycin (mildiomycin) (E.2.4), streptomycin (streptomycin) (E.2.5), oxytetracyclin (E.2.5) .2.6); F) signal transduction inhibitors MAP/histidine kinase inhibitors: fluoroimid (F.1.1), iprodione (F.1.2), procymidone ( F.1.3), vinclozolin (F.1.4), fludioxonil (F.1.5); G protein inhibitors: quinoxyfen (F.2.1); G) lipids and membranes Synthesis inhibitors Phospholipid biosynthesis inhibitors: edifenphos (G.1.1), iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane ) (G.1.4); lipid peroxidation: dicloran (G.2.1), quintozene (G.2.2), tecnazene (G.2.3) , tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7); phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1), flumorph (flumorph) (G.3.2), mandipropamid (G.3.3), pyrimorph (pyrimorph) ( G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7); affect cell membrane permeability and Compounds of fatty acids: propamocarb (G.4.1); inhibitors of oxidized sterol-binding proteins: oxathiapiprolin (G.5.1), methanesulfonic acid 2-{3-[2-(1 -{[3,5-bis(difluoromethyl-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5- Dihydro-1,2-oxazol-5-yl}phenyl ester (G.5.2), 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H) methanesulfonate -pyrazol-1-yl]acetyl}piperidin-4-yl)1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5yl}-3- Chlorophenyl ester (G.5.3), 4-[1-[2-[3-(difluoromethyl)-5-methyl-pyrazol-1-yl]acetyl]-4-piperidinyl] -N-tetralin-1-yl-pyridine-2-carboxamide (G.5.4), 4-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl] Acetyl]-4-piperidinyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.5), 4-[1-[2-[3-(difluoromethyl )-5-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.6) , 4-[1-[2-[5-cyclopropyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetraline-1- Base-pyridine-2-carboxamide (G.5.7), 4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4 -Piperidinyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl) Fluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetral-1-yl-pyridine-2-carboxamide (G.5.9), 4-[1- [2-[3,5-bis(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N - tetralin-1-yl-pyridine-2-carboxamide (G.5.11); H) Inhibitor inorganic active substances with multi-site action: Bordeaux mixture (Bordeaux mixture) (H.1.1), copper (H. .1.2), copper acetate (H.1.3), copper hydroxide (H.1.4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7); thio and Dithiocarbamates: ferbam (H.2.1), zinc manganese (mancozeb) (H.2.2), manganese (maneb) (H.2.3), metam ) (H.2.4), so as not to rot (metiram) (H.2.5), methyl zinc Naipu (propineb) (H.2.6), get grace (thiram) (H.2.7), zinc Naipu (zineb) ( H.2.8), Yisui (ziram) (H.2.9); organochlorine compounds: anilazine (H.3.1), tetrachloroisobenzonitrile (chlorothalonil) (H.3.2), tetrachlordane ( captafol) (H.3.3), captan (captan) (H.3.4), folpet (H.3.5), Yifaling (dichlorofluanid) (H.3.6), dichlorophen (dichlorophen) ( H.3.7), hexachlorobenzene (H.3.8), pentachlorophenol (H.3.9) and its salts, phthalide (H.3.10), methyl tolylfluanid (H.3.11); Guanidines and others: guanidine (H.4.1), dodine (H.4.2), dodine free base (H.4.3), biguanide salt (guazatine) (H.4.4), biguanide salt acetate (H. .4.5), Kerejing (iminoctadine) (H.4.6), Kerejing Triacetate (H.4.7), Kerejing Ginseng (Alkanebenzenesulfonate) (H.4.8), Nitrithioquinone (dithianon )(H.4.9), 2,6-dimethyl-1H,5H-[1,4]dithia

And[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraketone (H.4.10); I) Cell wall synthesis inhibitor Glucan synthesis inhibition Agents: validamycin (I.1.1), polyoxin B (I.1.2); melanin synthesis inhibitors: pyroquilon (I.2.1), trisethazole (tricyclazole) (I.2.2), carpropamid (I.2.3), dicyclomet (I.2.4), fenoxanil (I.2.5); J) plants Protection inducers Acibenzolar-S-methyl (acibenzolar-S-methyl) (J.1.1), probenazole (J.1.2), isotianil (J.1.3) , tiadinil (J.1.4), prohexadione-calcium (J.1.5); phosphonates: fosetyl (J.1.6), fosetyl-aluminum (fosetyl- aluminum) (J.1.7), phosphorous acid and its salts (J.1.8), calcium phosphonate (J.1.11), potassium phosphonate (J.1.12), potassium bicarbonate or sodium bicarbonate (J.1.9), 4 Cyclopropyl-N-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide (J.1.10); K) Unknown mode of action bronopol (K.1.1) , chinomethionat (K.1.2), cyflufenamid (K.1.3), cymoxanil (K.1.4), dazomet (K.1.5), michamycin Debacarb (K.1.6), diclocymet (K.1.7), diclomezine (K.1.8), difenzoquat (K.1.9), wild swallow Methylsulfate (K.1.10), diphenylamine (K.1.11), fenitropan (K.1.12), fenpyrazamine (K.1.13), fluorinated bacteria Amine (flumetover) (K.1.14), flusulfamide (flusulfamide) (K.1.15), flutinib (flutianil) (K.1.16), hypersensitive protein (harpin) (K.1.17), sulfacarb ( Metha-sulfocarb) (K.1.18), nitrapyrin (K.1.19), nitrothal-isopropyl (K.1.20), tolprocarb (K.1.21), fast Oxin-copper (K.1.22), proquinazid (K.1.23), tebufloquin (K.1.24), tecloftalam (K.1.25) , imidazosin (triazoxide) (K.1.26), N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl Base-N methylformamidine (K.1.27), N'(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl Base-N-methylformamidine (K.1.28), N'-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl] Oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1.29), N'-(5-bromo-6-indan-2-yl Oxygen-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine (K.1.30), N'-[5-bromo-6-[1-(3,5- Difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.31), N'-[5-bromo-6-( 4-isopropylcyclohexyloxy)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.32), N'[5 bromo-2-methyl -6-(1-phenylethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.33), N'-(2-methyl-5-trifluoro Methyl-4-(3-trimethylsilyl-propoxy)-phenyl)-N-ethyl-N-methylformamidine (K.1.34), N'-(5-difluoromethyl -2-methyl-4-(3-trimethylsilyl-propoxy)-phenyl)-N-ethyl-N-methylformamidine (K.1.35), 2-(4-chloro-benzene Base)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5 base]-2-prop-2-ynyloxy-acetamide (K.1.36), 3 [5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidine-3-yl]-pyridine (pyrisoxazole (pyrisoxazole)) (K.1.37), 3-[5 -(4-methylphenyl)-2,3-dimethyl-isoxazolidine-3 base]-pyridine (K.1.38), 5-chloro-1(4,6-dimethoxy-pyrimidine -2-yl)-2-methyl-1H-benzimidazole (K.1.39), (Z) 3 amino-2-cyano-3-phenyl-prop-2-enoic acid ethyl ester (K. 1.40), picarbutrazox (K.1.41), N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino] Oxymethyl]-2-pyridyl]amyl carbamate (K.1.42), N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl- Methylene]amino]oxymethyl]-2-pyridyl]but-3-ynyl carbamate (K.1.43), 2-[2-[(7,8-difluoro-2- Methyl-3-quinolinyl)oxy]-6-fluoro-phenyl]propan-2-ol (K.1.44), 2-[2-fluoro-6-[(8-fluoro-2-methyl -3-quinolyl)oxy]phenyl]propan-2-ol (K.1.45), quinofumelin (quinofumelin) (K.1.47), 9-fluoro-2,2-dimethyl-5 -(3-quinolinyl)-3H 1,4 benzoxazepine (K.1.49), 2-(6-benzyl-2-pyridyl)quinazoline (K.1.50), 2-[ 6-(3-fluoro-4methoxy-phenyl)-5-methyl-2-pyridyl]quinazoline (K.1.51), dichlorobentiazox (K.1.52), N' -(2,5-Dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine (K.1.53). Such as the pesticidal mixture of claim 2, wherein the compound II is selected from the following group: M.2. GABA-gated chloride channel antagonists, M.3 sodium channel modulators, M.4 nicotine acetylcholine Alkaline receptor agonist, M.5 Nicotinic acetylcholine receptor ectopic activator, M.6 Chloride channel activator of avermectins and milbemycins, M.9 Chitin TRPV channel modulator, M.13 Oxidative phosphorylation decoupler via disruption of proton gradient, M.15 Chitin biosynthesis type 0 inhibitor, M.16 Chitin biosynthesis type 1 inhibitor , M.22 Voltage-dependent sodium channel blockers, M.23 Inhibitors of acetyl CoA carboxylase, M.28 Rianodine receptor modulators of diamides, M.29: Chord regulator, M.UN.9.b): Fluxametamide, M.29.28 oxazosulfyl, Respiratory inhibitor: Inhibitor of complex III of Qo site, Qi site Inhibitors of complex III, inhibitors of complex II, sterol biosynthesis inhibitors, lipid and membrane synthesis inhibitors, cell wall synthesis inhibitors, plant protection inducers, diclocymet (K. 1.7), Tolprocarb (K.1.21) and picarbutrazox (K.1.41). The pesticidal mixture according to claim 2 or 3, wherein the ratio of the compound of formula I-R-1 or its salt to the compound II is between 10000:1 and 1:10000. The pesticidal mixture according to claim 2 or 3, wherein the ratio of the compound of formula I-R-1 or its salt to the compound II is between 1000:1 and 1:1000. A pesticidal composition comprising a liquid or solid carrier and a compound of formula I-R-1 as defined in Claim 1 or a salt thereof or a pesticidal pest as defined in any one of Claims 2 to 5 mixture of substances. A non-therapeutic method for controlling insects, acarids or nematodes, comprising exposing insects, acarids or nematodes or their food supply, habitat, breeding ground or their location with a pesticidally effective amount of A compound of formula I-R-1 or a salt thereof or a pesticidal mixture as defined in any one of claims 2 to 5 is contacted. A method for protecting plants from attack or infestation by insects, acarids or nematodes, comprising making the plant or the soil or water in which the plant grows and a pesticidally effective amount of formula I-R-1 as defined in claim 1 Compounds or salts thereof or pesticidal mixtures as defined in any one of claims 2 to 5. A method for protecting plant propagation material, which comprises making the plant propagation material and a pesticidally effective amount of the compound of formula I-R-1 as defined in claim 1 or a salt thereof or any one of claim 2 to 5 Exposure to pesticidal mixtures as defined in the subparagraph. The method of claim 8 or claim 9, wherein the plant is a rice plant and the insect is selected from the following group: Hemiptera: brown planthopper-brown rice hopper ( Nilaparvata lugens ) brown planthopper-spotted planthopper ( Laodelphax striatellus ) white-backed planthopper - white-backed planthopper ( Sogatella furcifera ) white leafhopper - white-winged leafhopper ( Cofana spectrum ) green leafhopper - two-spotted black-tailed leafhopper ( Nephotettix virescens ), black-striped black-tailed leafhopper ( N .nigriceps ), black-tailed leafhopper ( N. cincticeps ), Malayan black-tailed leafhopper ( N. malayanus ) electric leafhopper - electric light leafhopper ( Recilia dorsalis ) corn orange leafhopper - two-star leafhopper ( Cicadulina bipunctata ) purple Leafhopper-Macrosteles fascifrons ( Macrosteles fascifrons ) Rice ear bug, Rice bug ( Leptocorisa oratorius ), Rice spider bug ( L.acuta ) Rice brown bug-Rice green bug ( Nezara viridula ) Pygomenida varipennis ), Eysarcoris ( Eysarcoris ), Tibraca limbatriventris , Eysarcoris ventralis small bedbugs- Oebalus poecilus , American rice bugs ( O.pugnax )- Rice bug ( Blissus leucopterus leucopterus ) rice mealybug, rice pink mealybug ( Brevennia rehi ), subcane mealybug ( Pseudococcus saccharicola ) rice aphid, red-bellied tube aphid ( Rhopalosiphum rufiabdominalis ), wheat long tube aphid ( Macrosiphum avenae ) , Hysteroneura setariae ( Hysteroneura setariae ), Tetraneuro nigriabdominalis ( Tetraneuro nigriabdominalis ) Bean root aphid - Cotton root aphid ( Smynthurodes betae ) Lepidoptera: Rice bract insect - straight grained rice butterfly ( Parnara guttata ), evening eye Butterfly ( Melanitis Ieda ismene ) rice borer/strip borer - Chilo suppressalis ( Chilo suppressalis ), black-headed stripe borer ( Chilo polychrusus ), spotted grass borer ( Chilo partellus ), seven-star rice borer ( Chilo plejadellus ) rice stem borer - rice multi Chilotraea polychrysa ( Chilotraea polychrysa ) large borer - large borer ( Sesamia inferens ) rice borer - rice borer ( Tryporyza ( = Scirpophaga) incertulas ) rice white borer - rice white borer ( Tryporyza innotata ) rice leaf roller / leaf roller -Cnaphalocrocis medinalis , Marasmia patnalis , M. exigua shaving worm/army insect-Oriental armyworm ( Pseudaletia separate ) green Caterpillar - Xanthodes transversa Rice green caterpillar - Rice borer ( Narnaga aenescens ) Green horned caterpillar - Twilight butterfly, Mycalesis sp ( Mycalesis sp ) Meadow armyworm - Spodoptera frugiperda Cut root Insects - armyworm ( Mythimna separata ) rice shell insect - rice three-spot borer ( Nymphula depunctalis ) black caterpillar, deer moth ( Amata sp. ) long caterpillar - real hairy shrub moth ( Mocis frugalis ) yellow caterpillar, hookworm ( Psalis pennatula ) rice semi-brown inchworm, Pseudomonas oryzae, Chrysodeixis chalcites grass moth-rice leaf-cutting wild borer ( Herpetogramma licarsisalis ) sugarcane borer-small sugarcane borer ( Diatraea saccharalis ) corn stem borer- South American Corn Borer ( Elasmopalpus lignosellus ) Striped Geometrid- South American Mocis latipes European Corn Borer- Corn Borer ( Ostrinia nubilalis ) Mexican Rice Borer- Mexican Rice Borer ( Eoreuma loftini ) Coleoptera: Rice Weevil- Rice water weevil ( Lissorhopterus oryzophilus ) rice weevil - rice weevil ( Echinocnemus squamous ) rice weevil - rice negative mud worm ( Oryzophagus oryzae ) rice iron beetle - rice iron armor ( Diclodispa armigera ) rice leaf beetle - rice leaf beetle ( Oulema oryzae ) rice black bug - rice black bug ( Scotinophora vermidulate , S.vermidulate , S.lurida ), wide-winged black bug ( S.latiuscula ) rice flea beetle - black concave shank flea beetle ( Chaetocnima basalis ) maggot - white scale beetle ( Leucopholis irrorata ), White-scaled Beetle, Phyllophaga sp , Heteronychus sp Scarab-Argentine Diloboderus abderus Weevil- Sphenophorus spp Grape Colaspis brunnea , C. louisianae rice pollen beetle, Chilolaba acuta Diptera: stalk fly - Chlorops oryzae - Japanese rice water fly ( Agromyza oryzae ) rice water fly / rice stalk fly - rice stem water fly ( Hydrellia sasakii ) rice water fly / rice small miner - rice leafminer ( Hydrellia griseola ) rice gall mosquito - rice gall Mosquitoes (Orseolia (= Pachydiplosis) oryzae ) Seedling flies - Atherigona oryzae Rice midges - Chironomus cavazzai , Chironomus spp , Cricotopus spp Thysanoptera: Rice thrips -Chloethrips oryzae , Stenochaetothrips biformis , Perrisothrips sp. , Hoplothrips sp. Orthoptera: Rice Grasshopper, Isocane Hieroglyphus banian , Hieroglyphus nigrorepletus , Catantops pinguis , Attractomorpha burri , A. crenulate , A. psittacina psittacina ), A. Bedeli , Oxya adenttata , Oxya ebneri , Oxya hyla intracata , Acrida turricata , Locusta migratoria manilensis ) mole crickets, African mole crickets ( Grylotalpa africana ) crickets: Gryllus bimaculatus , Teleogryllus occipitalis , Euscyrtus concinus katydid-long-winged katydids ( Conocephalus longipennis ) Isoptera: Termites - Macrotermes gilvus , Syntermes molestans Hymenoptera: Ants - Tropical Fire Ants ( Solenopsis geminata ) Rice Stem Apex Nematodes - Leaf Bud Nematodes ( Aphelenchotdes besseyi ) Steotarsonemus pinki ) Crustacea: Limulus-Jia Peng Limulus ( Triops longicaudatus ), Crab-shaped Limulus ( T.cancriformis ) Rice crayfish-Procambarus clarkii ( Procambarus clarkii ), Morris green crayfish ( Orconectes virilis ). A seed comprising the compound of formula I-R-1 or a salt thereof as defined in claim 1 or the pesticidal mixture as defined in any one of claims 2 to 5 in an amount of 0.1 g to 10 kg per 100 kg of seeds.