PESTICIDALLY ACTIVE AMIDE COMPOUNDS

FIELD OF THE INVENTION

The present invention relates to novel pesticidally active amide compounds and in particular heteroaromatic amide compounds, to compositions comprising those compounds, and to their use in agriculture, for example in controlling insect pests and/or pests of the order Acarina damaging crops. In addition, the present invention relates to a method for controlling insect pests and/or pests of the order Acarina damaging crops in which the compounds or the compositions of the present invention are applied.

BACKGROUND OF THE INVENTION

In view of the increasing world population and the associated increased demand for nourishments, the productivity of cultivated growth needs to be improved. Yet, environmental influences on cultivation, such as soil pest, can considerably influence agricultural harvest. For example, Lepidoptera are the second most diverse pest insect order outnumbered only by beetles. There is hardly any cultivated plant that is not attacked by at least one lepidopteran pest. Thus, there is a constant need for novel pesticidally active compounds which should also exhibit a favorable ecological profile, i.e. not be toxic for non-target organisms, such as bees, and not show aquatoxicity.

The present invention therefore aims the provision of pesticidally active compounds and to compositions thereof which are useful in agriculture. In particular, the present invention aims to provide novel compounds which are active against insect pests and/or pests of the order Acarina damaging crops, and which therefore can be used as agricultural agent and in methods of controlling these animal pests.

SUMMARY OF THE INVENTION

The present invention is based on the finding that the above object can be solved by novel compounds having a specific structure that includes an amide and a (hetero)aromatic moiety.

That is, in a first aspect, the present invention provides a compound of formula I: [Formula I] wherein X is 0 or S;

Y is a direct bond or an optionally substituted alkylene group;

R ¹ is hydrogen, OH, or is selected from C ₁ -C ₆ alkyl, C ₁ -C ₆ cyanoalkyl, aminocarbonylC ₁ -C ₆ alkyl, hydroxycarbonylC ₁ -C ₆ alkyl, C ₁ -C ₆ nitroalkyl, trimethylsilaneC ₁ -C ₆ alkyl, C ₁ -C ₃ alkoxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ - C ₆ haloalkenyl, C ₂ -C ₆ alkynyl, C ₂ -C ₆ haloalkynyl, C ₃ -C ₄ cycloalkyl C ₁ -C ₂ alkyl-, oxetan-3- yl-CH2-, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl and benzyl, each of which is optionally substituted;

R ³ is hydrogen, optionally substituted C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₃ -C ₆ cycloalkyl or C ₃ -C ₆ heterocycloalkyl, CN, or C ₂ -C ₃ alkynyl;

L is an optionally substituted carbo- or heterocycle; or L and R ³ may be linked to form a carbo- or heterocycle;

Q ¹ is an optionally substituted carbo- or heterocycle; and

Q ² is an optionally substituted carbo- or heterocycle or C(O)N(R ^4a R ^4b ) with R ^4a being selected from the group consisting of hydrogen, C ₁ -C ₆ aikyi, and C ₁ -C ₆ haloalkyl; and R ^4b hydrogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, optionally substituted C ₃ -C ₆ cycloalkyl, C ₂ - C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₃ alkoxy C ₁ -C ₄ alkyl-, cyanoC ₁ -C ₆ alkyl-, optionally substituted phenyl, optionally substituted phenyl C ₁ -C ₂ alkyl-, optionally substituted heterocyclyl, optionally substituted heterocyclylC ₁ -C ₂ alkyl-, optionally substituted heteroaryl, optionally substituted heteroarylC ₁ -C ₂ alkyl-, and oxetanyl; or

R ^4a and R ^4b together with the nitrogen atom to which they are attached form a 4- to 6- membered heterocyclyl, which is optionally substituted and optionally comprises 1 or 2 additional heteroatoms, independently selected from N, 0 and S(O)r , and r is 1 or 2; or an agrochemically acceptable salt thereof, a stereoisomer thereof, an enantiomer thereof, a tautomer thereof or an N-oxide thereof.

In a second aspect, the present invention provides a composition comprising a compound of formula I as defined in the first aspect, one or more auxiliaries and/or adjuvants, and optionally one or more other active ingredients.

In a third aspect, the present invention provides a use of the compound according to the first aspect or a composition according to the second aspect in controlling insect pests and/or pests of the order Acarina damaging crops.

In a fourth aspect, the present invention provides a method of controlling insect pests and/or pests of the order Acarina damaging crops which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an effective amount of a compound as defined in the first aspect of the invention or a composition as defined in the second aspect of the invention.

In a fifth aspect, the present invention provides compounds which may be useful intermediates in the preparation of the compounds according to the first aspect, as well as the use of any of these compounds in the preparation of a compound according to the first aspect, and a process for preparing a compound according to the first aspect that involves any of these compounds.

In a further aspect, the present invention provides a method for the protection of plant propagation material from the attack by insects and/or the order Acarina damaging crops, which comprises treating the propagation material or the site, where the propagation material is planted, with an effective amount of a compound as defined in the first aspect or a composition as defined in the second aspect of the present invention. In another aspect, the present invention provides a plant propagation material, such as a seed, comprising, or treated with or adhered thereto, a compound of formula I as defined in the first aspect or a composition as defined in the second aspect of the present invention.

In a sixth aspect, the present invention may provide compounds with improved human and environmentally profiles compared to other products used to control insect pests and/or pests of the order Acarina in certain crops.

In the following, the invention and definitions as used herein to describe the invention will be set out in more detail.

DEFINITIONS

In the present disclosure, the following definitions are applicable.

The term "C ₁ -C _n alkyl” as used herein refers to a saturated straight-chain or branched hydrocarbon radical attached via any of the carbon atoms having 1 to n carbon atoms, for example, any one of the radicals methyl, ethyl, n-propyl, 1 -methylbutyl, 2- methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, n-pentyl, 1 ,1- dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2 -methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 , 1 -dimethylbutyl, 1 ,2-dimethylbutyl, 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, or 1-ethyl-2- methylpropyl.

The term "C ₁ -C _n haloalkyl" as used herein refers to a straight-chain or branched saturated alkyl radical attached via any of the carbon atoms having 1 to n carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these radicals may be replaced by fluorine, chlorine, bromine and/or iodine, i.e. , for example, any one of chloro methyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2- dif luoroethy I, 2 ,2 , 2-trifl uoroethy 1 , 2-chloro-2- fluoroethyl, 2-chloro-2,2-difluoroethyl,

2.2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3- fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl,

2.3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3- trichloropropyl, 2, 2, 3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2- fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4- fluorobutyl, 4-chloro butyl, 4-bromobutyl or nonafluorobutyl. According a term "C ₁ - C ₂ fluoroalkyl" would refer to a C ₁ -C ₂ alkyl radical which carries 1 , 2, 3, 4, or 5 fluorine atoms, for example, any one of difluoromethyl, trifluoromethyl, 1 -fluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1 ,1 ,2,2-tetrafluoroethyl or pentafluoroethyl.

The term "C ₁ -C _n alkoxy" as used herein refers to a straight-chain or branched saturated alkyl radical having 1 to n carbon atoms (as mentioned above) which is attached via an oxygen atom, i.e., for example, any one of the radicals methoxy, ethoxy, n-propoxy, 1 -methylethoxy, n-butoxy, 1 -methylpropoxy, 2-methylpropoxy or 1 ,1 -dimethylethoxy. The term “haloC ₁ -C _n alkoxy" as used herein refers to a C ₁ - C _n alkoxy radical where one or more hydrogen atoms on the alkyl radical is replaced by the same or different halo atom(s) - examples include tnfluoromethoxy, 2- fiuoroethoxy, 3-fluoropropoxy, 3,3,3-trifluoropropoxy, 4-chlorobutoxy.

The term “C ₁ -C _n cyanoalkyl” as used herein refers to a straight chain or branched saturated C ₁ -C _n alkyl radical having 1 to n carbon atoms (as mentioned above), where one of the hydrogen atoms in these radicals is be replaced by a cyano group: for example, cyanomethyl, 2-cyanoethyl, 2-cyanopropyl, 3-cyanopropyl, 1- (cyanomethyl)-2-ethyl, 1-(methyl)-2 -cyanoethyl, 4-cyanobutyl, and the like.

The term “C ₃ -C _n cycloalkyl” as used herein refers to 3-n membered cycloalkyl groups such as cyclopropane, cyclobutane, cyclopentane and cyclohexane.

The term “ C ₃ -C ₄ cycloalkyl-C ₁ -C ₂ alkyl” as used herein refers to 3 or 4 membered cycloalkyl group with either a methylene or ethylene group, which methylene or ethylene group is connected to the rest of the molecule. In the instance, the C ₃ - C ₄ cycloalkyl-C ₁ -C ₂ alkyl- group is substituted, the substituent(s) can be on the cycloalkyl group and/or on the alkyl group.

The term “C ₃ -C _n cycloalkylcarbonyl” as used herein refers to a 3-n membered cycloalkyl group attached to a carbonyl (C=O) group, which carbonyl group is connected to the rest of the molecule. Similarly the terms “C ₁ -C _n alkylcarbony”, “C ₁ - C _n alkoxycarbonyl”, “phenyloxycarbonyl” and “benzyloxycarbonyl” as used herein refers to an alkyl, alkoxy, phenyloxy and benzyloxy group respectively attached to a carbonyl (C=O) group, which carbonyl group is connected to the rest of the molecule. The term “C ₃ -C ₆ cycloalkylC ₁ -C ₄ haloalkoxy” as used herein refers to a 3 to 6 membered cycloalkyl group connected to a 1 to 4 membered haloalkoxy, which haloalkoxy group is connected to the rest of the molecule.

The term “aminocarbonylC ₁ -C _n alkyl” as used herein refers to an alkyl radical where one of the hydrogen atoms in the radical is replaced by CONH2 group.

The term “hydroxycarbonylC ₁ -C _n alkyl” as used herein refers to an alkyl radical where one of the hydrogen atoms in the radical is replaced by COOH group.

The term “C ₁ -C _n alkylsulfanyl” as used herein refers to a C ₁ -C _n alkyl moiety linked through a sulfur atom. Similarly, the term “C ₁ -C _n haloalkylthio” or “C ₁ - C _n haloalkylsulfanyl” as used herein refers to a C ₁ -Cnhaloalkyl moiety linked through a sulfur atom. Similarly, the term “C ₃ -C _n cycloalkylsulfanyl” refers to 3-n membered cycloalkyl moiety linked through a sulfur atom.

The term “C ₁ -C _n alkylsulfinyl” as used herein refers to a C ₁ -C _n alkyl moiety linked through the sulfur atom of the S(=O) group. Similarly, the term “C ₁ -C _n haloalkylsulfinyl “or “C ₁ -C _n haloalkylsulfinyl” as used herein refers to a C ₁ -C _n haloalkyl moiety linked through the sulfur atom of the S(=O) group.

Similarly, the term “C ₃ -C _n cycloalkylsulfinyl” refers to 3-n membered cycloalkyl moiety linked through the sulfur atom of the S(=O) group.

The term “C ₁ -C _n alkylsulfonyl” as used herein refers to a C ₁ -C _n alkyl moiety linked through the sulfur atom of the S(=O)2 group. Similarly, the term “C ₁ - C _n haloalkylsulfonyl “ or “C ₁ -C _n haloalkylsulfonyl“ as used herein refers to a C ₁ - C _n haloalkyl moiety linked through the sulfur atom of the S(=O)2 group. Similarly, the term “C ₃ -C _n cycloalkylsulfonyl” refers to 3-n membered cycloalkyl moiety linked through the sulfur atom of the S(=O)2 group

The term “trimethylsilaneC ₁ -C _n alkyl” as used herein refers to an alkyl radical where one of the hydrogen atoms in the radical is replaced by a -Si(CHs)3 group.

The term “C ₂ -C _n alkenyl” as used herein refers to a straight or branched alkenyl chain having from two to n carbon atoms and one or two double bonds, for example, ethenyl, prop-1 -enyl, but-2-enyl.

The term “C ₂ -C _n haloalkenyl” as used herein refers to a C ₂ -C _n alkenyl moiety substituted with one or more halo atoms which may be the same or different.

The term “C ₂ -C _n alkynyl” as used herein refers to a straight or branched alkynyl chain having from two to n carbon atoms and one triple bond, for example, ethynyl, prop-2- ynyl, but-3-ynyl,

The term “C ₂ -C _n haloalkynyl” as used herein refers to a C ₂ -C _n alkynyl moiety substituted with one or more halo atoms which may be the same or different. Halogen or “halo” is generally fluorine, chlorine, bromine or iodine. This also applies, correspondingly, to halogen in combination with other meanings, such as haloalkyl

The term “heteroaryl” as used herein refers to a 5- or 6-membered aromatic monocyclic ring having one or more heteroatoms independently selected from, for example, N, 0 and S. Examples of heteroaryls J-1 to J-35 with their respective bonding site indicated as an arrow are shown below but are not limited thereto.

The term “optionally substituted” as used herein means that the group referenced is either unsubstituted or is substituted by one or more substituents, for example, “C ₃ -C ₄ cycloalkyl is optionally substituted with 1 or 2 halo atoms” means C ₃ -C ₄ cycloalkyl, C ₃ -C ₄ cycloalkyl substituted with 1 halo atom and C ₃ -C ₄ cycloalkyl substituted with 2 halo atoms.

As used herein, the term ''controlling'' refers to reducing the number of pests, eliminating pests and/or preventing further pest damage such that damage to a plant or to a plant derived product is reduced.

As used herein, the term "pest" refers to insects, and molluscs that are found in agriculture, horticulture, forestry, the storage of products of vegetable origin (such as fruit, grain and timber); and those pests associated with the damage of man-made structures. The term pest encompasses all stages in the life cycle of the pest.

As used herein, the term "effective amount" refers to the amount of the compound, or a salt thereof, which, upon single or multiple applications provides the desired effect.

An effective amount is readily determined by the skilled person in the art, by the use of known techniques and by observing results obtained under analogous circumstances. In determining the effective amount, a number of factors are considered including, but not limited to: the type of plant or derived product to be applied; the pest to be controlled & its lifecycle; the particular compound applied; the type of application; and other relevant circumstances.

In each of the following aspects and embodiments of the invention, "consisting essentially" and inflections thereof are a preferred embodiment of "comprising" and its inflections, and "consisting of” and inflections thereof are a preferred embodiment of "consisting essentially of” and its inflections.

DETAILED DESCRIPTION OF THE INVENTION

Embodiments according to the invention are provided as set out below. The disclosure in the present application makes available each and every combination of these embodiments disclosed in the following.

Compounds of formula I

The compound according to the first aspect of the invention is characterized by having in combination an amide moiety and a (hetero)aromatic moiety. Specifically, the compound according to the first aspect of the invention corresponds to the following formula I: [Formula I] wherein

X is 0 or S;

Y is a direct bond or an optionally substituted alkylene group;

R ¹ is hydrogen, OH, or is selected from C ₁ -C ₆ alkyl, C ₁ -C ₆ cyanoalkyl, aminocarbonylC ₁ -C ₆ alkyl, hydroxycarbonylC ₁ -C ₆ alkyl, C ₁ -C ₆ nitroalkyl, trimethylsilaneC ₁ -C ₆ alkyl, C ₁ -C ₃ alkoxy-C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ - C ₆ haloalkenyl, C ₂ -C ₆ alkynyl, C ₂ -C ₆ haloalkynyl, C ₃ -C ₄ cycloalkylC ₁ - C ₂ alkyl-, oxetan-3- yl-CH ₂ -, C ₁ -C ₆ alkylcarbonyl, C ₁ -C ₆ alkoxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl and benzyl, each of which is optionally substituted; R ³ is hydrogen, optionally substituted C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₃ -C ₆ cycloalkyl or C ₃ -C ₆ heterocycloalkyl, CN, or C ₂ -C ₃ alkynyl;

L is an optionally substituted carbo- or heterocycle; or L and R ³ may be linked to form a carbo- or heterocycle as indicated by the dotted line in formula I;

Q ¹ is an optionally substituted carbo- or heterocycle; and

Q ² is an optionally substituted carbo- or heterocycle or C(O)N(R ^4a R ^4b ) with R ^4a being selected from the group consisting of hydrogen, C ₁ -C ₆ alkyl, and C ₁ -C ₆ haloalkyl; and R ^4b hydrogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, optionally substituted C ₃ -C ₆ cycloalkyl, C ₂ - C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₃ alkoxyC ₁ -C ₄ alkyl-, cyanoC ₁ -C ₆ alkyl-, optionally substituted phenyl, optionally substituted phenylC ₁ -C ₂ alkyl-, optionally substituted heterocyclyl, optionally substituted heterocyclylC ₁ -C ₂ alkyl-, optionally substituted heteroaryl, optionally substituted heteroarylC ₁ -C ₂ alkyl-, and oxetanyl; or

R ^4a and R ^4b together with the nitrogen atom to which they are attached form a 4- to 6- membered heterocyclyl, which is optionally substituted and optionally comprises 1 or 2 additional heteroatoms, independently selected from N, O and S(O)r , and r is 1 or 2.

The compound according to the first aspect of the invention may also be an agrochemically acceptable salt of the compound of formula I, a stereoisomer of the compound of formula I, an enantiomer of the compound of formula I, a tautomer of the compound of formula I or an N-oxide of the compound of formula I.

As defined above, the groups defined for the compound of formula I that are referenced to be optionally substituted may either be unsubstituted or substituted by one or more substituents. For example, the groups of R ¹ which are optionally substituted may be substituted with a substituent, preferably selected from halogen, C ₁ -C ₆ alkoxy and C ₁ -C ₆ haloalkyl. In one exemplary embodiment, R ¹ may be C ₃ - C ₄ cycloalkylC ₁ -C ₂ alkyl, wherein the C ₃ -C ₄ cycloalkyl may be substituted with 1 or 2 halogen atoms. In another exemplary embodiment, R ¹ may be benzyl which is substituted with one, two or three substituents independently selected from halogen, C ₁ -C ₆ alkoxy and C ₁ -C ₆ haloalkyl.

In an exemplary embodiment of each aspect of the invention, R ¹ is

A. hydrogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ cyanoalkyl, aminocarbonylC ₁ -C ₆ alkyl, hydroxycarbonyl C ₁ -C ₆ alkyl, C ₁ -C ₆ nitroalkyl, trimethylsilaneC ₁ -C ₆ alkyl, C ₁ -C ₃ alkoxy-C ₁ - C ₆ alkyl, C ₁ - C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ alkynyl, C ₂ -C ₆ haloalkynyl, C ₃ -C ₄ cycloalkylC ₁ -C ₂ alkyl-, C ₃ - C ₄ cycloalkylC ₁ -C ₂ alkyl- wherein the C ₃ -C ₄ cycloalkyl group is substituted with 1 or 2 halogen atoms, oxetan-3-yl-CH ₂ -, C ₁ -C ₃ alkylcarbonyl, C ₁ -C ₃ alkoxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, or benzyl; or

B. hydrogen, C ₁ -C ₆ alkyl, C ₁ ~C ₆ cyanoalkyl, aminocarbonylC ₁ -C ₆ alkyl, hydroxycarbonylC ₁ -C ₆ alkyl, C ₁ -C ₆ nitroalky I, trimethylsilaneC ₁ -C ₆ alkyl, C ₁ -C ₃ alkoxy-C ₁ - C ₆ alkyl, C ₁ - C ₆ haloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C _B haloalkenyl, C ₂ -C _B alkynyl, C ₂ -C _B haloalkynyl, C ₃ -C ₄ cycloalkylC ₁ -C ₂ alkyl-, benzyloxycarbonyl, or benzyl; or C. hydrogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ cyanoalkyl, aminocarbonylC ₁ -C ₆ alkyl, hydroxycarbonylC ₁ -C ₆ alkyl, C ₁ -C ₃ alkoxy-C ₁ -C ₈ alkyl, C ₁ - C ₈ haloalkyl, C ₂ -C ₈ alkenyl, C ₂ - C ₈ haloalkenyl, C ₂ -C ₈ alkynyl, C ₂ - C ₆ haloalkynyl, C ₃ -C ₄ cycloalkylC ₁ -C ₂ alkyl- benzyloxycarbonyl, or benzyl; or

D. hydrogen, C ₁ -C ₈ alkyl, C ₁ -C ₈ cyanoalkyl, C ₁ -C ₃ alkoxy-C ₁ -C ₈ alkyl, C ₁ - C ₈ haloalkyl, C ₂ - C ₆ alkenyl, C ₂ -C ₈ haloalkenyl, C ₂ -C ₈ alkynyl, C ₂ -C ₈ haloalkynyl, C ₃ -C ₄ cycloalkylC ₁ -C ₂ alkyl- benzyloxycarbonyl, or benzyl; or

E. hydrogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ cyanoalkyl, C ₁ -C ₄ alkoxy-C ₁ -C ₃ alkyl, C ₁ - C ₄ haloalkyl, C ₂ - C ₄ alkenyl, C ₂ -C ₄ haloalkenyl, C ₂ -C ₄ alkynyl, C ₂ -C ₄ haloalkynyl, C ₃ -C ₄ cycloalkylC ₁ -C ₂ alkyl- benzyloxycarbonyl, or benzyl; or

F. hydrogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ cyanoalkyl, C ₁ -C ₃ alkoxy-C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₂ - C ₄ alkenyl, C ₂ -C ₄ haloalkenyl, C ₂ -C ₄ alkynyl, C ₂ -C ₄ haloalkynyl, C ₃ -C ₄ cycloalkylC ₁ -C ₂ alkyl- benzyloxycarbonyl, or benzyl; or

G. hydrogen, methyl, ethyl, cyanomethyl, methoxymethyl, fluorinated C ₁ -C ₃ alkyl, cyclopropyl-methyl, allyl, propargyl, benzyloxycarbonyl, or benzyl; or

H. hydrogen, methyl, ethyl, mono- or difluoroethyl, allyl, propargyl or cyclopropyl- methyl; or

I. hydrogen, methyl, 2-fluoroethyl, propargyl or cyclopropyl-methyl.

In a preferred embodiment of each aspect of the invention, R ¹ is hydrogen, C ₁ -C ₆ alkyl, phenyl or benzyl, preferably R ¹ is hydrogen or C ₁ -C ₆ alkyl, more preferably R ¹ is hydrogen.

In a preferred embodiment of each aspect of the invention, the moiety Q ¹ -Q ² is wherein, Q ² is phenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl or thiazolyl each of which is optionally substituted; and in Q _a , R ^5a and R ^5b are independently selected from hydrogen, halogen, CN, C ₁ - C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₃ -C ₄ cycloalkyl, C ₁ -C ₃ alkoxy and C ₁ -C ₃ haloalkoxy; in Q _b , A ³ is N, and A ⁴ , A ⁵ and A ⁶ are independently selected from N, CH and CR ⁶ ; in Q _c , A ³ is C, A ⁴ is 0 or S, and A ⁵ and A ⁶ are independently selected from N, CH and CR ⁶ ; in Qd, A ³ is C, A ⁴ and A ⁶ are independently selected from N, CH and CR ⁶ , and A ⁵ is 0 or S; in Q _e , A ³ is N, A ⁴ and A ⁵ are independently selected from N, CH and CR ⁶ , and A ⁶ is 0 or S; and

R ⁶ is independently selected from hydrogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₃ - C ₄ cycloalkyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ alkoxyC(O)-, (C ₁ -C ₃ alkoxy^CH-, halogen, CN, NH ₂ C(O), amino, (C ₁ -C ₃ alkyl)amino, di(C ₁ -C ₃ alkyl)amino, hydroxy, C ₃ - C ₄ halocycloalkyl, C ₃ -C ₄ cyanocycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ - C ₆ alkynyl, C ₂ -C ₆ haloalkynyl, C ₁ -C ₄ haloalkylsulfanyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ - C ₄ haloalkylsulfonyl, C ₁ -C ₄ alkylsulfanyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ - C ₃ alkoxy-C ₁ -C ₃ alkyl, C ₁ -C ₃ alkoxy-C ₁ -C ₃ alkoxy-C ₁ -C ₃ alkyl, (C ₁ -C ₃ alkyl)sulfonylamino, (C ₁ -C ₃ alkyl)sulfonyl(C ₁ -C ₃ alkyl)amino, (C ₁ -C ₃ alkyl)NHC(O), (C ₁ -C ₃ alkyl) ₂ NC(O), (C ₁ - C ₃ cycloalkyl)NHC(O), (C ₁ -C ₃ cycloalkyl)(C ₁ -C ₃ alkyl)NC(O), (C ₁ -C ₃ alkyl)C(O)(C ₁ - C ₃ alkyl)N, (C ₁ -C ₃ alkyl)C(O)NH, (C ₁ -C ₃ alkyl)C(O), (C ₁ -C ₃ alkoxy)C(O), HC(O), diphenylmethanimine, C ₁ -C ₃ haloalkoxy, optionally substituted phenyl, or a optionally substituted 5-membered heteroaromatic ring.

In an exemplary embodiment, R ⁶ in Q _a , Qb, Qc, Qd and Q _e represents an optionally substituted phenyl or an optionally substituted 5-membered heteroaromatic ring. That is, the phenyl or the 5-membered heteroaromatic ring may independently be unsubstituted or substituted with one or more substituents independently selected from C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₃ -C ₄ cycloalkyl, halogen, CN and hydroxyl.

In a preferred embodiment of each aspect of the invention, the moiety Q ¹ -Q ² is represented by Q ^a , Q ^b , Q ^c , Q ^d or Q ^e and

A. in Qb, A ³ is N, A ⁴ and A ⁵ are N and A ⁶ is CH or CR ⁶ ; or

A ³ is N, A ⁴ is N, A ⁵ is CH or CR ⁶ and A ⁶ is N; or

A ³ is N, A ⁴ is CH or CR ⁶ , A ⁵ and A ⁶ are N; or

A ³ is N, A ⁴ and A ⁵ are CH or CR ⁶ and A ⁶ is N; or

A ³ is N, A ⁴ and A ⁶ are CH or CR ⁶ and A ⁵ is N; or

A ³ is N, A ⁴ is N, A ⁵ and A ⁶ are CH or CR ⁶ ; or

A ³ is N, A ⁴ , A ⁵ and A ⁶ are CH or CR ⁶ ; or

A ³ is N, A ⁴ is N, A ⁵ is N and A ⁶ is N; preferably, A ³ is N, A ⁴ and A ⁵ are CH or CR ⁶ and A ⁶ is N; or A ³ is N, A ⁴ , A ⁵ and A ⁶ are CH or CR ⁶ ; or A ³ is N, A ⁴ is N, A ⁵ and A ⁶ are CH or CR ⁶ ;

B. in Q _c ,

A ³ is C, A ⁴ is O, and A ⁵ and A ⁶ are CH or CR ⁶ ; or A ³ is C, A ⁴ is S, and A ⁵ and A ⁶ are CH or CR ⁶ ; or A ³ is C, A ⁴ is O, and A ⁵ and A ⁶ are N; or A ³ is C, A ⁴ is S, and A ⁵ and A ⁶ are N; or A ³ is C, A ⁴ is O, A ⁵ is CH or CR ⁶ and A ⁶ is N; preferably, A ³ is C, A ⁴ is O, A ⁵ is N, and A ⁶ is CH or CR ⁶ or A ³ is C, A ⁴ is O, A ⁵ is CH or CR ⁶ and A ⁶ is N;

C. in Qd, A ³ is C, A ⁴ and A ⁶ are CH or CR ⁶ , and A ⁵ is O;

A ³ is C, A ⁴ and A ⁶ are CH or CR ⁶ , and A ⁵ is S; or

A ³ is C, A ⁴ and A ⁶ are N, and A ⁵ is 0; or

A ³ is C, A ⁴ and A ⁶ are N, and A ⁵ is S; or

A ³ is C, A ⁴ is CH or CR ⁶ , A ⁵ is 0 and A ⁶ is N; or

A ³ is C, A ⁴ is CH or CR ⁶ , A ⁵ is S and A ⁶ is N; or

A ³ is C, A ⁴ is N, A ⁵ is S and A ⁶ is CH or CR ⁶ ; or preferably A ³ is C, A ⁴ is N, A ⁵ is 0 and A ⁶ is CH or CR ⁶ or A ³ is C, A ⁴ and A ⁶ are N, and A ⁵ is 0;

D. in Q _e , A ³ is N, A ⁴ and A ⁵ are N, and A ⁶ is 0; or

A ³ is N, A ⁴ and A ⁵ are N, and A ⁶ is S; or

A ³ is N, A ⁴ and A ⁵ are CH or CR ⁶ , and A ⁶ is 0; or

A ³ is N, A ⁴ and A ⁵ are CH or CR ⁶ , and A ⁶ is S; or

A ³ is N, A ⁴ is N, A ⁵ is CH or CR ⁶ , and A ⁶ is 0; or

A ³ is N, A ⁴ is N, A ⁵ is CH or CR ⁶ , and A ⁶ is S; or

A ³ is N, A ⁴ is CH or CR ⁶ , A ⁵ is N, and A ⁶ is 0; or

A ³ is N, A ⁴ is CH or CR ⁶ , A ⁵ is N, and A ⁶ is S; or preferably A ³ is N, A ⁴ and A ⁵ are CH or CR ⁶ , and A ⁶ is 0; or A ³ is N, A ⁴ and A ⁵ are CH or CR ⁶ , and A ⁶ is S.

More preferably, Q ¹ -Q ² is represented by Qb, and preferably, in Qb, A ³ is N, A ⁴ is N, A ⁵ is CH or CR ⁶ and A ⁶ is N, more preferably A ⁵ is CH; or

Q ¹ -Q ² is represented by Q _c , and preferably, in Q _c , A ³ is C, A ⁴ is O, A ⁵ is CH or CR ⁶ and A ⁶ is N, more preferably A ⁵ is CH; or

Q ¹ -Q ² is represented by Qd, and preferably, in Qd, A ³ is C, A ⁴ is N, A ⁵ is 0 and A ⁶ is

CH or CR ⁶ , more preferably A ⁶ is CH; or

Q ¹ -Q ² is represented by Q _e , and preferably, in Q _e , A ³ is N, A ⁴ and A ⁵ are CR ⁶ CH, and A ⁶ is O, more preferably A ⁴ and A ⁵ are CH.

In an embodiment of each aspect of the invention, R ^5a in Q _a is

A. hydrogen, halogen, CN, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₃ -C ₄ cycloalkyl, C ₁ -C ₃ alkoxy or C ₁ - C ₃ haloalkoxy; or

B. hydrogen, halogen, CN, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₃ -C ₄ cycloalkyl or C ₁ - C ₃ alkoxy; or

C. hydrogen, halogen, CN, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl or C ₁ -C ₃ alkoxy; or

D. hydrogen, halogen, CN, C ₁ -C ₃ alkyl or C ₁ -C ₃ alkoxy; or

E. hydrogen or halogen; or

F. hydrogen.

In an embodiment of each aspect of the invention, R ^5b in Q _a is A. hydrogen, halogen, CN, C ₁ -C ₃ haloalkyl, C ₃ -C ₄ cycloalkyl, C ₁ -C ₃ alkoxy, or C ₁ - C ₃ haloalkoxy; or

B. hydrogen, halogen or C ₁ -C ₃ alkoxy; or

C. hydrogen.

In an embodiment of each aspect of the invention, R ⁶ in Q _b , Q _c , Q _d and Q _e may be

A. hydrogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₃ -C ₄ cycloalkyl, C ₁ -C ₃ alkoxy, halogen, C ₁ - C ₃ alkoxy-C ₁ - C ₃ alkyl, C ₁ -C ₃ alkoxy-C ₁ -C ₃ alkoxy-C ₁ -C ₃ alkyl, (C ₁ -C ₃ alkyl)C(O), (C ₁ - C ₃ alkoxy)C(O), HC(O), C ₁ - C ₃ haloalkoxy or a 5-membered heteroaromatic ring wherein the 5-membered heteroaromatic ring can be optionally substituted with one to three substituents selected from C ₁ -C ₃ alkyl, C ₁ - C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₃ - C ₄ cycloalkyl, halogen, CN or hydroxy; or

B. hydrogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₃ -C ₄ cycloalkyl, C ₁ -C ₃ alkoxy, halogen, C ₁ - C ₃ alkoxy-C ₁ - C ₃ alkyl, C ₁ -C ₃ alkoxy-C ₁ -C ₃ alkoxy-C ₁ -C ₃ alkyl, (C ₁ -C ₃ alkyl)C(O), (C ₁ - C ₃ alkoxy)C(O), HC(O) or C ₁ -C ₃ haloalkoxy; or

C. hydrogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₃ -C ₄ cycloalkyl, C ₁ -C ₃ alkoxy, halogen, Cl, Br, C ₁ - C ₃ alkoxy-C ₁ -C ₃ alkyl, C ₁ -C ₃ alkoxy-C ₁ -C ₃ alkoxy-C ₁ -C ₃ alkyl, (C ₁ -C ₃ alkyl)C(O), (C ₁ - C ₃ alkoxy)C(O), or C ₁ -C ₂ haloalkoxy; or

D. hydrogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ alkoxy, C ₃ -C ₄ cycloalkyl, C ₁ -C ₃ haloalkoxy, halogen, C ₁ - C ₃ alkoxy- C ₁ -C ₃ alkyl, C ₁ -C ₃ alkoxy-C ₁ -C ₃ alkoxy-C ₁ -C ₃ alkyl, (C ₁ -C ₃ alkyl)C(O), HC(O), or (C ₁ - C ₃ alkoxy)C(O); or

E. hydrogen, C ₁ - C ₂ alkyl, C ₁ -C ₂ alkoxy, C ₃ -C ₄ cycloalkyl, C ₁ -C ₂ haloalkoxy, halogen, C ₁ - C ₂ alkoxy- C ₁ -C ₂ alkyl, C ₁ -C ₂ alkoxy-C ₁ -C ₂ alkoxy-C ₁ -C ₂ alkyl, (C ₁ -C ₂ alkyl)C(O), HC(O), or (C ₁ - C ₂ alkoxy)C(O); or

F. hydrogen, methyl, trifluoromethoxy, methoxy, cyclopropyl, 2,2-difluroroethoxy, 2,2,2- trifluroroethoxy, difluoromethoxy, 2,2,2-trifluroroethyl, chloro, bromo, methoxyethoxy, methylcarbonyl, or methoxycarbonyl; or

G. hydrogen.

In an embodiment of each aspect of the invention, the moiety Q ¹ -Q ² may be represented by one of the following structures Q ¹ -1 to Q ¹ -33:

In a preferred embodiment of each aspect of the invention, Q ¹ -Q ² is represented by Q ¹ -1 , Q ¹ -2, Q ¹ -3, Q ¹ -4, Q ¹ -6, Q ¹ -9, Q ¹ -10, Q ¹ -11 , Q ¹ -18, more preferably Q ¹ -Q ² is represented by Q ¹ -1 , Q ¹ -9 or Q ¹ -18, even more preferably Q ¹ -Q ² is Q ¹ -1. In a preferred embodiment of each aspect of the invention, Q ² is an optionally substituted carbo- or heterocycle. In particular, in a more preferred embodiment Q ² is phenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl or thiazolyl each of which is either unsubstituted or substituted with one, two or three substituents. These substituents may independently be selected from C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₃ - C ₄ cycloalkyl, halogen, hydroxyl, CN, trimethyl silyl, C ₁ -C ₆ haloalkoxy, C ₂ - C ₆ haloalkenyloxy, C ₂ -C ₆ haloalkynyloxy, C ₃ -C ₄ halocycloalkoxy. C ₃ -C ₆ cycloalkylC ₁ - C ₄ haloalkoxy, NH ₂ C(O)-, NH ₂ C(S)-, (OH)N=C(NH ₂ )- and a 5-membered heteroaryl ring that may be optionally substituted by one, two or three substituents independently selected from halogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy and C ₁ -C ₃ haloalkoxy.

In an alternative embodiment of each aspect of the invention, Q ² is C(O)N(R ^4a R ^4b ), wherein R ^4a is selected from the group consisting of hydrogen, C ₁ -C ₆ aikyi, and C ₁ - C ₆ haloalkyl; and R ^4b is selected from the group consisting of hydrogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl substituted with one, two or three substituents independently selected from R ⁸ , C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ - C ₆ alkynyl, C ₁ -C ₃ alkoxyC ₁ -C ₄ alkyl-, cyanoC ₁ -C ₆ alkyl- phenyl, phenyl substituted with one, two or three substituents independently selected from R ⁹ , phenylC ₁ -C ₂ alkyl- phenylC ₁ -C ₂ alkyl- substituted with one, two or three substituents independently selected from R ¹⁰ , heterocyclyl, heterocyclyl substituted with one, two or three substituents independently selected from R ¹¹ , heterocyclylC ₁ -C ₂ alkyl-, heterocyclylC ₁ -C ₂ alkyl- substituted with one, two or three substituents independently selected from R ¹² , heteroaryl, heteroaryl substituted with one, two or three substituents independently selected from R ¹³ , heteroarylC ₁ -C ₂ alkyl-, heteroarylC ₁ - C ₂ alkyl- substituted with 1 to 3 substituents independently selected from R ¹³ , and oxetanyl; or

R ^4a and R ^4b together with the nitrogen atom to which they are attached form a 4- to 6- membered heterocyclyl, which optionally comprises 1 or 2 additional heteroatoms, independently selected from N, O and S(O)r, and wherein said heterocyclyl moiety is optionally substituted by 1 or 2 substituents independently selected from R ¹⁴ , and r is 1 or 2; wherein R ⁸ is independently selected from cyano, OH, halogen, oxo (=0), C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, and C ₁ -C ₃ alkoxy;

R ⁹ is independently selected from cyano, OH, halogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy and C ₁ -C ₃ haloalkoxy;

R ¹⁰ is independently selected from cyano, OH, halogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy and C ₁ -C ₃ haloalkoxy;

R ¹¹ independent of the heterocyclyl group, is independently selected from cyano, OH, halogen, oxo (=0), C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, and C ₁ -C ₃ alkoxy; R ¹² independent of the heterocyclylC ₁ -C ₂ alkyl- group, is independently selected from cyano, OH, halogen, oxo (=O), C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, and C ₁ -C ₃ alkoxy;

R ¹³ is independent of the heteroarylC ₁ -C ₂ alkyl- group, is independently selected from cyano, OH, halogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy and C ₁ -C ₃ haloalkoxy; and

R ¹⁴ is independently selected from cyano, OH, halogen, oxo (=0), C ₁ -C ₃ alkyl, C ₁ - C ₃ haloalkyl, and C ₁ -C ₃ alkoxy.

More preferably, Q ² is phenyl, pyridinyl, pyrim idinyl, pyrazinyl or pyridazinyl, each of which is optionally substituted, preferably Q ² is pyridinyl or pyrim idinyl, and more preferably Q ² is pyridin-2-yl or pyrim idin-2-yl. In an alternative embodiment, Q ² is phenyl or pyridinyl which is preferably substituted with one substituent, more preferably the substituent is in para-position to Q ¹ ; and even more preferably the substituent is cyano.

In an embodiment of each aspect of the invention, Q ² is

A. phenyl, pyridinyl, pyrimidinyl or thiazolyl; wherein the phenyl, pyridinyl, pyrimidinyl or thiazolyl, independently of each other, is optionally substituted with one substituent selected from C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ - C ₃ alkoxy, C ₃ -C ₄ cycloalkyl, halo, hydroxyl, CN, C ₁ -C ₆ haloalkoxy, C ₂ -C ₆ haloalkenyloxy, C ₂ - C ₆ haloalkynyloxy, C ₃ - C ₄ halocycloalkoxy, C ₃ -C ₆ cycloalkylC ₁ -C ₄ haloalkoxy, NH ₂ C(O)-, NH ₂ C(S)-, (OH)N=C(NH ₂ )-, J-13 optionally substituted by one, two or three substituents independently selected from halogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy and C ₁ -C ₃ haloalkoxy, J-20 optionally substituted by one, two or three substituents independently selected from halogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy and C ₁ -C ₃ haloalkoxy and 1 H-tetrazol-5-yl; or

B. phenyl, pyridinyl, pyrimidinyl or thiazolyl, wherein the phenyl, pyridinyl, pyrimidinyl or thiazolyl, independently of each other, is optionally substituted with one substituent selected from C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ - C ₃ alkoxy, C ₃ -C ₄ cycloalkyl, halo, hydroxyl, CN, C ₁ -C ₆ haloalkoxy, C ₂ -C ₆ haloalkenyloxy, C ₂ - C ₆ haloalkynyloxy, C ₃ - C ₄ halocycloalkoxy, C ₃ -C ₆ cycloalkylC ₁ -C ₄ haloalkoxy, NH ₂ C(O)-, NH ₂ C(S)-, (OH)N=C(NH ₂ )-, J-13 optionally substituted by C ₁ -C ₃ haloalkyl, J-20 optionally substituted by C ₁ -C ₃ haloalkyl and 1 H-tetrazol-5-yl; or

C. pyridinyl, wherein the pyridinyl is optionally substituted with one substituent selected from C ₁ - C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₃ -C ₄ cycloalkyl, halo, hydroxyl, CN, C ₁ -C ₆ haloalkoxy, C ₂ -C ₆ haloalkenyloxy, C ₂ -C ₆ haloalkynyloxy, C ₃ - C ₄ halocycloalkoxy, C ₃ -C ₆ cycloalkylC ₁ -C ₄ haloalkoxy, NH ₂ C(O)-, NH ₂ C(S)-, (OH)N=C(NH ₂ )-, J-13 optionally substituted by C ₁ -C5haloalkyl, J-20 optionally substituted by C ₁ -C ₃ haloalkyl and 1 H-tetrazol-5-yl; or D. pyrim idinyl; wherein the pyrimidinyl is optionally substituted with one substituent selected from C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₃ -C ₄ cycloalkyl, halo, hydroxyl, CN, C ₁ -C ₆ haloalkoxy, C ₂ -C ₆ haloalkenyloxy, C ₂ -C ₆ haloalkynyloxy, C ₃ - C ₄ halocycloalkoxy, C ₃ -C ₆ cycloalkylC ₁ -C ₄ haloalkoxy, NH ₂ C(O)-, NH ₂ C(S)-, (OH)N=C(NH ₂ )-, J-13 optionally substituted by trifluoromethyl, J-20 optionally substituted by trifluoromethyl and 1 H-tetrazol-5-yl; or

E. phenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl or thiazolyl, wherein the phenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl or thiazolyl is optionally substituted with one substituent selected from C ₁ -C ₃ alkyl, C ₁ - C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₃ - C ₄ cycloalkyl, F, Cl, Br, CN and C ₁ -C ₆ haloalkoxy; or

F. phenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl or thiazolyl, wherein the phenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl or thiazolyl is optionally substituted with one substituent selected from C ₁ -C ₃ alkyl, C ₃ - C ₄ cycloalkyl, F, Cl, Br, CN and C ₁ - C ₆ haloalkoxy; or

G. phenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl or thiazolyl, wherein the phenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl or thiazolyl is optionally substituted with one substituent selected from cyclopropyl, F, Cl, Br, CN, trifluoromethoxy, difluoromethoxy, 2,2-difluoroethoxy and 2,2,2-trifluoroethoxy;

H. pyridinyl, or pyrimidinyl, wherein the pyridinyl or pyrimidinyl is optionally substituted with one substituent selected from cyclopropyl, F, Cl, Br, CN, trifluoromethoxy, difluoromethoxy, 2,2- difluoroethoxy and 2,2,2-trifluoroethoxy; or

I. 5-cylopropylpyridinyl, 5-fluoropyridinyl, 5-chloropyridinyl, 5-bromopyridinyl, 5- difluoromethoxypyridinyl, 5-trifluoromethoxypyridinyl, 5-cyanopyridinyl, 5-(2,2- difluoroethoxy)-pyridinyl, 5-(2,2,2-trifluoroethoxy)-pyridinyl, pyridinyl, 5- cylopropylpyrimidinyl, 5-fluoropyrim idinyl, 5-chloropyrim idinyl, 5-bromopyrimidinyl, 5- difluoromethoxypyrim idinyl, 5- trifluoromethoxypyrimidinyl, 5-cyanopyrimidinyl, 5-(2,2- difluoroethoxy)-pyrim idinyl, 5-(2,2,2-trifluoroethoxy)-pyrimidinyl, or pyrimidinyl; or

J. 5-cylopropylpyridin-2-yl, 5-fluoropyridin-2-yl, 5-chloropyridin-2-yl, 5-bromopyridin-2- yl, 5- difluoromethoxypyridin-2-yl, 5-trifluoromethoxypyridin-2-yl, 5-cyanopyridin-2-yl, 5-(2,2- difluoroethoxy-pyridin-2-yl, 5-(2,2,2-trifluoroethoxy)-pyridin-2-yl, pyridin-2-yl, 5- cylopropylpyrimidin-2-yl, 5-fluoropyrimidin-2-yl, 5-chloropyrim idin-2-yl, 5- bromopyrimidin-2-yl, 5-difluoromethoxypyrimidin-2-yl, 5-trifluoromethoxypyrimidin-2- yl, 5-cyanopyrimidin-2-yl, 5-(2,2-difluoroethoxy)-pyrimidin-2-yl, 5-(2,2,2- trifluoroethoxy)-pyrimidin-2-yl, or pyrim idin-2-yl; or

K. pyrimidin-2-yl, pyridin-2-yl, 5-bromopyrimidin-2-yl, 5-bromopyridin-2-yl, 5- cyanopyrimidin-2-yl, or 5-cyanopyridin-2-yl; or

L. pyrimidin-2-yl, 5-bromopyrimidin-2-yl, 5-bromopyridin-2-yl, or 5-cyanopyridin-2-yl.

In an embodiment of each aspect of the invention, Q ² is

A. phenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl or thiazolyl, wherein the phenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl or thiazolyl, independent of each other, is optionally substituted with one substituent selected from C ₁ -C ₃ haloalkyl, C ₃ - C^ycloalkyl, halogen, cyano, C ₁ -C ₃ haloakoxy; or

B. pyridinyl, pyrim idinyl, pyrazinyl or pyridazinyl, wherein the pyridinyl, pyrimidinyl, pyrazinyl or pyridazinyl, independent of each other, is optionally substituted with one substituent selected from F, Cl, Br, CN, trifluoromethoxy, difluoromethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy and selected from optionally substituted triazolyl such as J-30 and optionally substituted J-25; or

C. pyridinyl or pyrimidinyl, wherein the pyridinyl or pyrimidinyl is optionally substituted with one substituent selected from C ₁ -C ₃ haloalkyl, C ₃ -C ₄ cycloalkyl, halogen, cyano, C ₁ - C ₃ haloakoxy and selected from optionally substituted triazolyl such as J-30 and optionally substituted J-25; or

D. pyridinyl or pyrimidinyl, wherein the pyridinyl or pyrimidinyl is optionally substituted with one substituent selected from cyclopropyl, F, Cl, Br, CN, trifluoromethoxy, difluoromethoxy, 2,2- difluoroethoxy and 2,2,2-trifluoroethoxy and selected from optionally substituted triazolyl such as J-30 and optionally substituted J-25; or

E. 5-cylopropylpyridinyl, 5-fluoropyridinyl, 5-chloropyridinyl, 5-bromopyridinyl, 5- difluoromethoxypyridinyl, 5-trifluoromethoxypyridinyl, 5-cyanopyridinyl, 5-(2,2- difluoroethoxyj-pyridinyl, 5-(2,2,2-trifluoroethoxy)-pyridinyl, pyridinyl, 5- cylopropylpyrimidinyl, 5-fluoropyrim idinyl, 5-chloropyrimidinyl, 5-bromopyrimidinyl, 5- difluoromethoxypyrim idinyl, 5- trifluoromethoxypyrimidinyl, 5-cyanopyrimidinyl, 5-(2,2- difluoroethoxy)-pyrim idinyl, 5-(2,2,2-trifluoroethoxy)-pyrimidinyl, pyrimidinyl, or 1 ,2,3- triazoly I; or

F. 5-cylopropylpyridin-2-yl, 5-fluoropyridin-2-yl, 5-chloropyridin-2-yl, 5-bromopyridin-2- yl, 5- difluoromethoxypyridin-2-yl, 5-trifluoromethoxypyridin-2-yl, 5-cyanopyridin-2-yl, 5-(2,2- difluoroethoxy)-pyridin-2-yl, 5-(2,2,2-trifluoroethoxy)-pyridin-2-yl, pyridin-2-yl, 5- cylopropylpyrimidin-2-yl, 5-fluoropyrim idin-2-yl, 5-chloropyrimidin-2-yl, 5- bromopyrimidin-2-yl, 5-difluoromethoxypyrimidin-2-yl, 5-trifluoromethoxypyrimidin-2- yl, 5-cyanopyrimidin-2-yl, 5- (2,2-difluoroethoxy)-pyrimidin-2-yl, 5-(2,2,2- trifluoroethoxy)-pyrimidin-2-yl, pyrimidin-2-yl, or 1 ,2,3-triazol-2-yl; or

G. 1 ,2,3-triazol-2-yl, pyrim idin-2-yl, or 5-cyanopyridin-2-yl.

In an exemplary embodiment of each aspect of the invention, Q ² may be represented by one of the following structures Q ² -1 to Q ² -26:

In an embodiment of each aspect of the present invention, Q ¹ -Q ² is Q ¹ -1 , wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -2, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -3, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -4, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -4, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or Q ¹ -Q ² is Q ¹ -5, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -6, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -7, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -8, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -9, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or Q ¹ -Q ² is Q ¹ -10, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -11 , wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -12, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -13, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -14, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -15, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -16, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -17, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -18, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -19, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -20, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -21 , wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -22, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -23, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -24, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -25, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -26, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -27, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -28, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -29, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -30, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -31 , wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or Q ¹ -Q ² is Q ¹ -32, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26; or

Q ¹ -Q ² is Q ¹ -33, wherein Q ² is represented by one of the structures of Q ² -1 to Q ² -26.

In an embodiment of each aspect of the present invention,

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -1 ; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -2; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -3; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -4; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -5; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -6; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -7; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -8; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -9; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -10; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -11 ; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -12; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -13; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -14; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -15; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -16; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -17; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -18; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -19; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -20; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -21 ; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -22; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -23; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -24; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -25; or

Q ¹ -Q ² is selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -26.

In a preferred embodiment in each of the aspects of the present invention, Q ¹ -Q ² is represented by Q ¹ -1 , Q ¹ -2, Q ¹ -3, Q ¹ -4, Q ¹ -6, Q ¹ -9, Q ¹ -10, Q ¹ -11 or Q ¹ -18, wherein Q ² is represented by Q ² -1 , Q ² -2, Q ² -4, Q ² -9 or Q ² -10. More preferably, Q ¹ -Q ² is represented by Q ¹ -1 , Q ¹ -9 or Q ¹ -18, wherein Q ² is represented by Q ² -1 , Q ² -2, Q ² -4, Q ² -9 or Q ² -10. Even more preferably Q ¹ -Q ² is Q ¹ -1 , wherein Q ² is represented by Q ² - 1 , Q ² -2, Q ² -4, Q ² -9 or Q ² -10.

In another preferred embodiment of the invention, Q ¹ -Q ² is represented by Q ¹ -1 , Q ¹ - 2, Q ¹ -3, Q ¹ -4, Q ¹ -6, Q ¹ -9, Q ¹ -10, Q ¹ -11 or Q ¹ -18, wherein Q ² is Q ² -1 , Q ² -2 or Q ² -9. More preferably, Q ¹ -Q ² is represented by Q ¹ -1 , Q ¹ -2, Q ¹ -3, Q ¹ -4, Q ¹ -6, Q ¹ -9, Q ¹ -10, Q ¹ -11 or Q ¹ -18, wherein Q ² is Q ² -1. Alternatively, Q ¹ -Q ² is represented by Q ¹ -1 , Q ¹ -2, Q ¹ -3, Q ¹ -4, Q ¹ -6, Q ¹ -9, Q ¹ -10, Q ¹ -11 or Q ¹ -18, wherein Q ² is Q ² -2. In a further alternative embodiment, Q ¹ -Q ² is represented by Q ¹ -1 , Q ¹ -2, Q ¹ -3, Q ¹ -4, Q ¹ -6, Q ¹ -9, Q ¹ -10, Q ¹ -11 or Q ¹ -18, wherein Q ² is Q ² -9.

In one embodiment of each aspect of the invention, L and R ³ may be connected to form a carbo- or heterocycle. In one embodiment, the compound of the first aspect of the present invention in which L and R ³ are connected to form a carbo- or heterocycle might conform to the following structures:

X-1 X-2 X-3 wherein X’ is 0 or S, A ¹ ’ and A ² ’ have the same definitions as A ¹ and A ² above; R’ and R” are independently selected from hydrogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ - C ₃ haloalkylthio, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy, halogen, NO2, SF5, CN, C(O)NH ₂ , C(O)OH, C(S)NH ₂ , C ₃ -C ₆ cycloalkyl that is optionally substituted, C ₃ - C ₆ cycloalkylcarbonyl, phenyl that is optionally substituted, heteroaryl that is optionally substituted, OR ⁷ , piperidin-2-one-1-yl, pyridin-2-one-1 -yl that is optionally substituted, azetidin-1-yl that is optionally substituted, pyrrolidin-1 -yl that is optionally substituted, C ₃ -C ₆ cycloalkylC ₁ -C ₄ alkyl that is optionally substituted, C ₃ -C ₆ cycloalkylC ₁ -C ₃ alkoxy that is optionally substituted, C ₁ -C ₃ cyanoalkyl, C ₁ -C ₃ cyanoalkoxy, C ₁ -C ₄ alkylsulfanyl that is optionally substituted, C ₁ -C ₄ alkylsulfonyl that is optionally substituted, C ₁ - C ₄ alkylsulfinyl that is optionally substituted, C ₃ -C ₆ cycloalkylsulfanyl, C ₃ - C ₆ cycloalkylsulfinyl and C ₃ -C ₆ Cycloalkylsulfonyl;

R ⁷ is phenyl, benzyl, heteroaryl or C ₃ -C ₆ cycloalkyl each of which is optionally substituted; and R ^p is selected from hydrogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ - C ₃ alkoxy, C ₁ -C ₃ haloalkoxy, halogen, CN and cyclopropyl; and Y’ and Z’ are independently selected from NH, NR ⁶ , CH, CR ⁶ , 0 and S.

In an exemplary embodiment, the carbo-or heterocycle formed by L and R ³ may be represented by the following moieties:

In a preferred embodiment of each aspect of the invention, L in formula I corresponds to the below structure: wherein A ¹ and A ² are independently selected from N, CH and CR ^P ;

R ^2a and R ^2b are independently selected from hydrogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ haloalkylthio, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy, halogen, NO2, SF5, CN, C(O)NH ₂ , C(O)OH, C(S)NH ₂ , C ₃ -C ₆ cycloalkyl that is optionally substituted, C ₃ - C ₆ cycloalkylcarbonyl, phenyl that is optionally substituted, heteroaryl that is optionally substituted, OR ⁷ , piperidin-2-one-1-yl, pyridin-2-one-1 -yl that is optionally substituted, azetidin-1-yl that is optionally substituted, pyrrolidin-1 -yl that is optionally substituted, C ₃ -C ₆ cycloalkylC ₁ -C ₄ alkyl that is optionally substituted, C ₃ -C ₆ cycloalkylC ₁ -C ₃ alkoxy that is optionally substituted, C ₁ -C ₃ cyanoalkyl, C ₁ -C ₃ cyanoalkoxy, C ₁ -C ₄ alkylsulfanyl that is optionally substituted, C ₁ -C ₄ alkylsulfonyl that is optionally substituted, C ₁ - C ₄ alkylsulfinyl that is optionally substituted, C ₃ -C ₆ cycloalkylsulfanyl, C ₃ - C ₆ cycloalkylsulfinyl and C ₃ -C ₆ Cycloalkylsulfonyl;

R ⁷ is phenyl, benzyl, heteroaryl or C ₃ -C ₆ cycloalkyl each of which is optionally substituted; and R ^p is selected from hydrogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ - C ₃ alkoxy, C ₁ -C ₃ haloalkoxy, halogen, CN and cyclopropyl.

That is, the compound of formula I preferably corresponds to the compound of formula l-X: [Formula l-X] wherein Q ¹ , Q ² , X, R ¹ , R ^2a , R ^2b , R ³ , A ¹ and A ² are defined as in each embodiment of the first aspect of the invention. In one embodiment of each aspect of the invention, R ^2a and R ^2b are independently selected from hydrogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ haloalkylthio, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy, halogen, NO ₂ , SF ₅ , CN, C(O)NH ₂ , C(O)OH, C(S)NH ₂ , C ₃ - C ₆ cycloalkyl that is optionally substituted with one, two or three substituents R ^x , C ₃ - C ₆ cycloalkylcarbonyl, phenyl that is optionally substituted with one, two or three substituents R ^x , heteroaryl that is optionally substituted with one, two or three substituents R ^x , OR ⁷ , piperidin-2-one-1 -yl that is optionally substituted with one or two substituents R ^x , pyridin-2-one-1 -yl that is optionally substituted with one or two substituents R ^x , azetidin-1 -yl that is optionally substituted with one or two substituents R ^x , pyrrolidin-1 -yl that is optionally substituted with one or two substituents R ^x , C ₃ -C ₆ cycloalkylC ₁ -C ₄ alkyl that is optionally substituted with one or two substituents R ^z , C ₃ -C ₆ cycloalkylC ₁ -C ₃ alkoxy that is optionally substituted with one or two substituents R ^x , C ₁ -C ₃ cyanoalkyl, C ₁ -C ₃ cyanoalkoxy, C ₁ -C ₄ alkylsulfanyl that is optionally substituted with one, two or three substituents R ^x , C ₁ -C ₄ alkylsulfonyl that is optionally substituted with one, two or three substituents R ^x , C ₁ -C ₄ alkylsulfinyl that is optionally substituted with one, two or three substituents R ^x , C ₃ -C ₆ cycloalkylsulfanyl, C ₃ -C ₆ cycloalkylsulfinyl and C ₃ -C ₆ Cycloalkylsulfonyl.

In this embodiment, each R ^x is independently selected from halogen, C ₁ -C ₃ alkyl, C ₁ - C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy, NO ₂ , SFs, CN, C(O)NH ₂ , C(S)NH ₂ , C ₁ - C ₄ haloalkylsulfanyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ - C ₄ haloalkylsulfonyl, C ₁ -C ₄ alkylsulfanyl, C ₁ -C ₄ alkylsulfinyl and C ₁ -C ₄ alkylsulfonyl; and each R ^z is independently selected from oxo, halogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy and CN.

In an embodiment of each aspect of the invention, R ^x is independently selected from

A. halogen, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy and CN; or

B. F, Cl, Br, OCF ₂ H, OCH ₃ and CN.

In an embodiment of each aspect of the invention, R ^p is independently selected from

A. hydrogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy, halogen, CN and cyclopropyl; or

B. hydrogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy, halogen and cyclopropyl; or

C. hydrogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl and C ₁ -C ₃ alkoxy; or

D. hydrogen, methyl, trifluoromethyl and methoxy; or

E. hydrogen.

In an embodiment of each aspect of the invention, R ^z is independently selected from

A. oxo, halogen, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy or CN; or

B. oxo, F, Cl, Br, OCF ₂ H, OCH ₃ or CN.

In an embodiment of each aspect of the invention, R ⁷ is A. phenyl, benzyl, heteroaryl, or C ₃ -C ₆ cycloalkyl, each of which, independent of each other, is optionally substituted with one substituent selected from R ^x ; or

B. phenyl, benzyl, cyclopropyl or cyclopropyl substituted with one substituent selected from R ^x .

In an embodiment of each aspect of the invention,

A. A ¹ is CR ^P and A ² is CR ^P or N; or

B. A ¹ is N and A ² is CR ^P or N; or

C. A ² is CR ^P and A ¹ is CR ^P or N; or

D. A ² is N and A ¹ is CR ^P or N; or

E. A ¹ and A ² are both CR ^P ; or

F. A ¹ and A ² are both N; or

G. A ¹ is CH and A ² is CH or N; or

H. A ¹ is N and A ² is CH or N; or

I. A ² is CH and A ¹ is CH or N; or

J. A ² is N and A ¹ is CH or N; or

K. A ¹ and A ² are both CH.

In a preferred embodiment of each aspect of the invention, A ¹ and A ² are the same, preferably A ¹ and A ² are both CR ^P or CH; more preferably A ¹ and A ² are both CH.

In an embodiment of each aspect of the invention, R ^2a in L is

A. hydrogen, halogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy, CN, C ₃ -C ₄ cycloalkyl, C ₃ -C ₆ cycloalkylcarbonyl, phenyl, heteroaryl selected from J-1 and J- 25 as defined above, each of C ₃ -C ₄ cycloalkyl, phenyl or heteroaryl, independently of each other, is substituted with one, two or three substituents R ^x _; 0 R ₆ , piperid in-2- one-1 -yl, pyridin-2-one-1-yl, azetidin-1 -yl optionally substituted with R ^x , pyrrolidin-1 -yl, C ₃ -C ₆ cycloalkylC ₁ -C ₄ alkyl optionally substituted with one or two substituents R ^z , C ₃ - C ₆ cycloalkylC ₁ -C ₃ alkoxy optionally substituted with R ^x , C ₁ - C ₃ cyanoalkyl, C ₁ - C ₃ cyanoalkoxy, C ₁ -C ₄ alkylsulfanyl optionally substituted by one, two or three substituents R ^x , C ₁ -C ₄ alkylsulfonyl optionally substituted by one, two or three substituents R ^x , or C ₁ - C ₄ alkylsulfinyl optionally substituted by one, two or three substituents R ^x ; or

B. hydrogen, halogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy, CN, C ₃ -C ₄ cycloalkyl, C ₃ -C ₆ cycloalkylcarbonyl, phenyl, pyrazolyl, each of C ₃ -C ₄ cycloalkyl, phenyl, pyrazolyl, independent of each other, is substituted with one, two or three substituents R ^x _; OR ⁷ , piperidin-2-one-1-yl, pyridin-2 -one-1 -yl, azetidin-1 -yl optionally substituted with R ^x , pyrrolidin-1 - yl, C ₃ -C ₆ cycloalkylC ₁ -C ₄ alkyl optionally substituted with one or two substituents R ^z , C ₃ -C ₆ cycloalkylC ₁ -C ₃ alkoxy optionally substituted with R ^x , C ₁ -C ₃ cyanoalkyl, C ₁ -C ₃ cyanoalkoxy, C ₁ -C ₄ alkylsulfanyl optionally substituted by one, two or three substituents R ^x , C ₁ -C ₄ alkylsulfonyl optionally substituted by one, two or three substituents R ^x , or C ₁ -C ₄ alkylsulfinyl optionally substituted by one, two or three substituents R ^x ; or

C. hydrogen, halogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy, CN, C ₃ -C ₄ cycloalkyl, C ₃ -C ₆ cycloalkylcarbonyl, phenyl or pyrazolyl, each of C ₃ - C ₄ cycloalkyl, phenyl, pyrazolyl, independent of each other, is substituted with one or two substituents R ^x , OR ⁷ , azetidin-1 -yl optionally substituted with R ^x , C ₃ - C ₆ cycloalkylC ₁ -C ₄ alkyl optionally substituted with one or two substituents R ^z , C ₃ - C ₆ cycloalkylC ₁ -C ₃ alkoxy optionally substituted with R _x , C ₁ - C ₄ alkylsulfanyl optionally substituted by one, two or three substituents R ^x , C ₁ -C ₄ alkylsulfonyl optionally substituted by one, two or three substituents R ^x , or C ₁ -C ₄ alkylsulfinyl optionally substituted by one, two or three substituents R ^x ; or

D. hydrogen, halogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy, CN, C ₃ - C ₄ cycloalkyl, C ₃ -C ₄ cycloalkyl substituted with one or two substituents R ^x _; C ₃ - C ₆ cycloalkylcarbonyl, OR ⁷ , C ₃ -C ₆ cycloalkylC ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkylC ₁ -C ₄ alkyl substituted with one or two substituents R ^z , C ₁ -C ₄ alkylsulfanyl, C ₁ -C ₄ alkylsulfanyl substituted by one, two or three substituents R ^x , C ₁ -C ₄ alkylsulfonyl, C ₁ - C ₄ alkylsulfonyl substituted by one, two or three substituents R _x , C ₁ -C ₄ alkylsulfinyl, or C ₁ -C ₄ alkylsulfinyl substituted by one, two or three substituents R ^x ; or

E. hydrogen, halogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy, CN, C ₃ -C ₄ cycloalkyl, C ₃ -C ₄ cycloalkyl substituted with one or two substituents independently selected from halogen, C ₁ -C ₃ alkyl and C ₁ -C ₃ haloalkyl, C ₃ - C ₄ cycloalkylcarbonyl, C ₃ -C ₄ cycloalkylmethyl, C ₃ -C ₄ cycloalkylmethyl substituted with one or two substituents independently selected from oxo, halogen, C ₁ -C ₃ alkyl and C ₁ -C ₃ haloalkyl, C ₁ -C ₂ alkylsulfanyl substituted with one, two or three halogens or C ₁ - C ₂ alkylsulfonyl substituted with one, two or three halogens; or

F. hydrogen, halogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy, cyclopropyl, cyclopropyl substituted with one or two substituents independently selected from halogen, methyl and trifluoromethyl, cyclopropylcarbonyl, cyclopropylmethyl substituted with one or two substituents independently selected from oxo, halogen and trifluoromethyl, C ₁ -C ₂ alkylsulfanyl substituted with one, two or three halogens, or C ₁ -C ₂ alkylsulfonyl substituted with one, two or three halogens; or

G. hydrogen, halogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ haloalkylsulfanyl, C ₁ - C ₃ alkoxy, C ₁ - C ₃ haloalkoxy, CN, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl substituted with one, two or three substituents independently selected from C ₁ -C ₃ alkyl, C ₁ - C ₃ haloalkyl, cyano and halogen, cyclopropylcarbonyl, C ₃ -C ₆ cycloalkylC ₁ -C ₄ alkyl, C ₃ - C ₆ cycloalkylC ₁ -C ₄ alkyl substituted with one to five substituents independently selected from oxo, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, cyano and halogen, C ₁ -C ₃ cyanoalkyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₃ -C ₆ cycloalkylsulfanyl, C ₃ -C ₆ cycloalkylsulfinyl, or C ₃ -C ₆ cycloalkylsulfonyl; or H. hydrogen, halogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ haloalkylsulfanyl, C ₁ - C ₃ alkoxy, C ₁ - C ₃ haloalkoxy, CN, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl substituted with one or two substituents independently selected from C ₁ -C ₃ haloalkyl, cyano and halogen, C ₃ -C ₄ cycloalkylcarbonyl, C ₃ - C6cycloalkylC ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkylC ₁ - C ₄ alkyl substituted with one, two or three substituents independently selected from oxo, C ₁ -C ₃ haloalkyl, cyano and halogen, C ₁ -C ₃ cyanoalkyl, C ₁ - C ₄ alkylsulfonyl, C ₁ - C ₄ haloalkylsulfonyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₃ - C ₆ cycloalkylsulfanyl, C ₃ -C ₆ cycloalkylsulfinyl, or C ₃ -C ₆ cycloalkylsulfonyl; or

I. hydrogen, halogen, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ haloalkylsulfanyl, C ₁ -C ₃ haloalkoxy, C ₃ - C ₆ cycloalkyl, C ₃ -C ₆ cycloalkyl substituted with one or two substituents independently selected from C ₁ - C ₃ haloalkyl, cyano and halogen, C ₃ -C ₄ cycloalkylcarbonyl, C ₃ - C6cycloalkylC ₁ -C ₄ alkyl, C ₃ - C ₆ cycloalkylC ₁ -C ₄ alkyl substituted with one, two or three substituents independently selected from oxo, C ₁ -C ₃ haloalkyl, cyano and halogen, C ₁ -C ₃ cyanoalkyl, (XUalkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ -C ₄ alkylsulfinyl, C ₁ - C ₄ haloalkylsulfinyl, C ₃ -C ₆ cycloalkylsulfanyl, C ₃ -C ₆ cycloalkylsulfinyl, or C ₃ - C ₆ cycloalkylsulfonyl; or

J. hydrogen, halogen, C ₃ -C ₄ cycloalkyl, C ₃ -C ₄ cycloalkylcarbonyl, C ₃ -C ₄ cycloalkyl-C ₁ - C ₂ alkyl optionally substituted with one or two substituents selected from oxo, halogen, C ₁ -C ₃ alkyl and C ₁ -C ₃ haloalkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ haloalkylsulfanyl, C ₁ - C ₃ haloalkysulfonyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy, or CN; or

K. halogen, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ haloalkylsulfanyl, C ₁ -C ₃ haloalkysulfonyl, or C ₁ - C ₃ haloalkoxy; or

L. halogen, C ₁ -C ₂ haloalkyl, C ₁ -C ₂ haloalkylsulfanyl, C ₁ -C ₂ haloalkysulfonyl, or C ₁ - C ₂ haloalkoxy; or

M. chlorine, fluorine, bromine, iodine, difluoromethyl, trifluoromethyl, trifluoromethylsulfanyl, or trifluoromethylsulfonyl; or

N. fluorine, chlorine, bromine, iodine, trifluoromethylsulfanyl, trifluoromethylsulfonyl, or trifluoromethyl; or

O. trifluoromethyl, bromine, or chlorine.

In an embodiment of each aspect of the invention, R ^2b is

A. hydrogen, halogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₃ -C ₄ cycloalkyl, cyclopropylcarbonyl, C ₃ - C ₆ cycloalkylC ₁ -C ₄ alkyl optionally substituted with one or two substituents R _z , C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy, or CN, C ₁ -C ₄ alkylsulfanyl optionally substituted by one, two or three substituents R ^x , C ₁ -C ₄ alkylsulfonyl optionally substituted by one, two or three substituents R ^x , or C ₁ -C ₄ alkylsulfinyl optionally substituted by one, two or three substituents R ^x ; or B. hydrogen, halogen, C ₃ -C ₄ cycloalkyl, cyclopropylcarbonyl, C ₃ -C ₄ cycloalkyl-C ₁ -C ₂ alkyl optionally substituted with one or two substituents selected from oxo, halogen, C ₁ - C ₃ alky I and C ₁ - Cshaloalkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ haloalkysulfanyl, C ₁ - C ₃ haloalkysulfonyl, C ₁ -C ₃ alkoxy, C ₁ - Cshaloalkoxy, or CN; or

C. halogen, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ haloalkylsulfanyl, C ₁ -C ₃ haloalkysulfonyl, or C ₁ - C ₃ haloalkoxy; or

D. halogen, C ₁ -C ₂ haloalkyl, C ₁ -C ₂ haloalkylsulfanyl, C ₁ -C ₂ haloalkysulfonyl, or C ₁ - C ₂ haloalkoxy; or

E. chlorine, fluorine, bromine, iodine, difluoromethyl, trifluoromethyl, trifluoromethylsulfanyl, or trifluoromethylsulfonyl; or

F. fluorine, chlorine, bromine, iodine, trifluoromethylsulfanyl, trifluoromethylsulfonyl, or trifluoromethyl; or

G. trifluoromethyl, bromine, or chlorine.

In a preferred embodiment of each aspect of the invention, R ^2a and R ^2b are independently selected from hydrogen, C ₁ -C ₃ alkyl, preferably C ₁ alkyl, C ₁ -C ₃ alkoxy, preferably C ₁ alkoxy, C ₁ -C ₃ haloalkoxy, preferably C ₁ haloalkoxy; and halogen, more preferably R ^2a and R ^2b are independently selected from C ₁ haloalkoxy; and halogen, even more preferably, R ^2a and R ^2b are fluorine or trifluoromethyl.

In a preferred exemplary embodiment of each aspect of the present invention, L is selected from the following moieties L-1 to L-40:

In an embodiment of each aspect of the present invention,

L is represented by L-1 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-2 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or

L is represented by L-3 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or

L is represented by L-4 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or

L is represented by L-5 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or

L is represented by L-6 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-7 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or

L is represented by L-8 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or

L is represented by L-9 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or

L is represented by L-10 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or

L is represented by L-11 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-12 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or

L is represented by L-13 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-14 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-15 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-16 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-17 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-18 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-19 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-20 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-21 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-22 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-23 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-24 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-25 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-26 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-27 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-28 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-29 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-30 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-31 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-32 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-33 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-34 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-35 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-36 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-37 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-38 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-39 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33; or L is represented by L-40 and Q ¹ -Q ² is represented by Q ¹ -1 to Q ¹ -33.

In each of the above embodiments, Q ² may be defined as above.

In an exemplary embodiment of each aspect of the invention, L is represented by one of L-1 to L-40 and Q ¹ -Q ² is represented by Q ¹ -1 , Q ¹ -2, Q ¹ -3, Q ¹ -4, Q ¹ -6, Q ¹ -9, Q ¹ -10, Q ¹ -11 or Q ¹ -18, wherein Q ² is represented by Q ² -1 , Q ² -2, Q ² -4, Q ² -9 or Q ² -10. More preferably, L is represented by one of L-1 to L-40 and Q ¹ -Q ² is represented by Q ¹ -1 , Q ¹ -9 or Q ¹ -18, wherein Q ² is represented by Q ² -1 , Q ² -2, Q ² -4, Q ² -9 or Q ² -10. Even more preferably, L is represented by one of L-1 to L-40 and Q ¹ -Q ² is Q ¹ -1 , wherein Q ² is represented by Q ² -1 , Q ² -2, Q ² -4, Q ² -9 or Q ² -10.

In another preferred embodiment of the invention, L is represented by one of L-1 to L-40 and Q ¹ -Q ² is represented by Q ¹ -1 , Q ¹ -2, Q ¹ -3, Q ¹ -4, Q ¹ -6, Q ¹ -9, Q ¹ -10, Q ¹ -11 or Q ¹ -18, wherein Q ² is Q ² -1 , Q ² -2 or Q ² -9. More preferably, L is represented by one of L-1 to L-40 and Q ¹ -Q ² is represented by Q ¹ -1 , Q ¹ -2, Q ¹ -3, Q ¹ -4, Q ¹ -6, Q ¹ -9, Q ¹ -10, Q ¹ -11 or Q ¹ -18, wherein Q ² is Q ² -1 . Alternatively, L is represented by one of L-1 to L- 40 and Q ¹ -Q ² is represented by Q ¹ -1 , Q ¹ -2, Q ¹ -3, Q ¹ -4, Q ¹ -6, Q ¹ -9, Q ¹ -10, Q ¹ -11 or Q ¹ -18, wherein Q ² is Q ² -2. In a further alternative embodiment, L is represented by one of L-1 to L-40 and Q ¹ -Q ² is represented by Q ¹ -1 , Q ¹ -2, Q ¹ -3, Q ¹ -4, Q ¹ -6, Q ¹ -9, Q ¹ -10, Q ¹ -11 or Q ¹ -18, wherein Q ² is Q ² -9.

In an embodiment of each aspect of the invention, Y is alkylene such as CH2 or a direct bond, preferably Y is CH2 or a direct bond, more preferably Y is a direct bond.

In an embodiment of each aspect of the invention, X is 0 or S, preferably X is 0.

In an embodiment of each aspect of the invention, R ³ may be selected from H, CH3,

CH ₂ CH ₃ , cyclo-propyl, CN, CF3,

In a preferred embodiment of each aspect of the invention, R ³ is selected from H and CH3. More preferably, R ³ is H.

The present invention, accordingly, makes available a compound of formula I having the substituents R ¹ , R ³ , Q ¹ , Q ² , X, Y and L as defined above in all combinations/each permutation.

In preferred exemplary embodiments of each aspect of the invention, it is made available a compound of formula I, wherein

A. the compound of formula I corresponds to a compound of formula l-X with X being O, Y being a direct bond or CH2, R ¹ being hydrogen, methyl, propargyl or cyclopropyl-methyl; R ³ being hydrogen, Q ¹ -Q ² being one of Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -1 to Q ² -26, A ¹ and A ² independently being CH or N, R ^2a and R ^2b independently being hydrogen, halogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₁ - C ₃ haloalkoxy, cyclopropyl, cyclopropyl substituted with one to two substituents independently selected from halogen, methyl and trifluoromethyl, cyclopropylcarbonyl, cyclopropylmethyl substituted with one to two substituents independently selected from oxo, halogen and trifluoromethyl, C ₁ -C ₂ alkylsulfanyl substituted with one to three halogens, or C ₁ -C ₂ alkylsulfonyl substituted with one to three halogens; or

B. the compound of formula I corresponds to a compound of formula l-X with X being O, Y being a direct bond or CH2, R ¹ being hydrogen, methyl, propargyl or cyclopropyl-methyl; R ³ being hydrogen, Q ¹ -Q ² being one of Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -1 to Q ² -26, A ¹ and A ² being, independently from each other, CH or N; R ¹ being hydrogen, methyl, propargyl or cyclopropyl-methyl; R ^2a being hydrogen, halogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy, cyclopropyl, cyclopropyl substituted with one to two substituents independently selected from halogen, methyl and trifluoromethyl, cyclopropylcarbonyl, cyclopropylmethyl substituted with one to two substituents independently selected from oxo, halogen and trifluoromethyl, or C ₁ -C ₂ alkylsulfanyl substituted with one to three halogens or C ₁ -C ₂ alkylsulfonyl substituted with one to three halogens;

R ^2b being hydrogen, halogen, C ₃ -C ₄ cycloalkyl, cyclopropylcarbonyl, C ₃ -C ₄ cycloalkyl- C ₁ -C ₂ alkyl optionally substituted with one to two substituents selected from oxo, halogen, C ₁ -C ₃ alkyl and C ₁ -C ₃ haloalkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ haloalkysulfanyl, C ₁ - C ₃ haloalkysulfonyl, C ₁ -C ₃ alkoxy, C ₁ -C ₃ haloalkoxy, or CN; R ³ being methyl; and Q ¹ -Q ² being selected from Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -1 to Q ² -8, wherein Q ² -1 to Q ² -8 is each optionally substituted with one substituent selected from C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ alkoxy, C ₃ -C ₄ cycloalkyl, halo, hydroxyl, CN, C ₁ - C ₆ haloalkoxy, C ₂ -C ₆ haloalkenyloxy, C ₂ -C ₆ haloalkynyloxy, C ₃ -C ₄ halocycloalkoxy, C ₃ - C ₆ cycloalkylC ₁ -C ₄ haloalkoxy, NH ₂ C(O)-, NH ₂ C(S)-, (OH)N=C(NH ₂ )-, J-13 optionally substituted by C ₁ -C ₃ haloalkyl, J-20 optionally substituted by C ₁ -C ₃ haloalkyl and 1 H- tetrazol-5-yl.

C. the compound of formula I corresponds to a compound of formula l-X with A ¹ and A ² being, independently from each other, CH or N; R ¹ being hydrogen, methyl, propargyl or cyclopropyl-methyl; R ^2a being halogen, C ₁ -C ₃ haloalkyl, C ₁ - C ₃ haloalkylsulfanyl, C ₁ -C ₃ haloalkysulfonyl, or C ₁ -C ₃ haloalkoxy; R ^2b being halogen, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ haloalkylsulfanyl, C ₁ -C ₃ haloalkysulfonyl, or C ₁ -C ₃ haloalkoxy; as R3 methyl; and, Q ¹ -Q ² being one of Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -1 to Q ² -26.

D. the compound of formula I corresponds to a compound of formula l-X with X being O, Y being a direct bond or CH2, R ¹ being hydrogen, methyl, propargyl or cyclopropyl-methyl; R ³ being hydrogen, Q ¹ -Q ² being one of Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -1 to Q ² -26, A ¹ and A ² being, independently from each other, CH or N; R ^2a being halogen, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ haloalkylsulfanyl, C ₁ - C ₃ haloalkysulfonyl, or C ₁ -C ₃ haloalkoxy; R ^2b being halogen, C ₁ -C ₃ haloalkyl, C ₁ - C ₃ haloalkylsulfanyl, C ₁ -C ₃ haloalkysulfonyl, or C ₁ -C ₃ haloalkoxy; and R ³ being methyl or hydrogen.

E. the compound of formula I corresponds to a compound of formula l-X with X being O, Y being a direct bond or CH2, R ¹ being hydrogen, methyl, propargyl or cyclopropyl-methyl; R ³ being hydrogen, Q ¹ -Q ² being one of Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -1 to Q ² -26, and A ¹ and A ² being, independently from each other, CH or N; R ^2a being halogen, C ₁ -C ₂ haloalkyl, C ₁ -C ₂ haloalkylsulfanyl, C ₁ - C ₂ haloalkysulfonyl, or C ₁ -C ₂ haloalkoxy; R ^2b being halogen, C ₁ -C ₂ haloalkyl, C ₁ - C ₂ haloalkylsulfanyl, C ₁ -C ₂ haloalkysulfonyl, or C ₁ -C ₂ haloalkoxy; and R ³ being methyl or hydrogen. F. the compound of formula I corresponds to a compound of formula l-X with X being O, Y being a direct bond or CH2, R ¹ being hydrogen, methyl, propargyl or cyclopropyl-methyl; R ³ being hydrogen, Q ¹ -Q ² being one of Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -1 to Q ² -26, and A ¹ and A ² being, independently from each other, CH or N; R ^2a being halogen, C ₁ -C ₂ haloalkyl, C ₁ -C ₂ haloalkylsulfanyl, C ₁ - C ₂ haloalkysulfonyl, or C ₁ -C ₂ haloalkoxy; R ^2b being halogen, C ₁ -C ₂ haloalkyl, C ₁ - C ₂ haloalkylsulfanyl, C ₁ -C ₂ haloalkysulfonyl, or C ₁ -C ₂ haloalkoxy; and R ³ being methyl or hydrogen.

G. the compound of formula I corresponds to a compound of formula l-X with X being O, Y being a direct bond or CH2, R ¹ being hydrogen, methyl, propargyl or cyclopropyl-methyl; R ^2a being chlorine, fluorine, bromine, iodine, difluoromethyl, trifluoromethyl, trifluoromethylsulfanyl, or trifluoromethylsulfonyl; R ³ being hydrogen, Q ¹ -Q ² being one of Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -1 to Q ² -26, and A ¹ and A ² being, independently from each other, CH or N; R ^2b being chlorine, fluorine, bromine, iodine, difluoromethyl, trifluoromethyl, trifluoromethylsulfanyl, trifluoromethylsulfonyl; and R ³ being methyl or hydrogen.

H. the compound of formula I corresponds to a compound of formula l-X with X being O, Y being a direct bond or CH2, R ¹ being hydrogen, methyl, propargyl or cyclopropyl-methyl; Q ¹ -Q ² being one of Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -1 to Q ² -26, A ¹ and A ² being, independently from each other, CH or N; R ^2a being chlorine, fluorine, bromine, iodine, difluoromethyl, trifluoromethyl, trifluoromethylsulfanyl, or trifluoromethylsulfonyl; R ^2b being chlorine, fluorine, bromine, iodine, difluoromethyl, trifluoromethyl, trifluoromethylsulfanyl, trifluoromethylsulfonyl; and R ³ being methyl or hydrogen.

I. the compound of formula I corresponds to a compound of formula l-X with X being O, Y being a direct bond or CH2, R ¹ being hydrogen, methyl, propargyl or cyclopropyl-methyl; Q ¹ -Q ² being one of Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -1 to Q ² -26, A ¹ and A ² being, independently from each other, CH or N; R ^2a being chlorine, fluorine, bromine, iodine, difluoromethyl, trifluoromethyl, trifluoromethylsulfanyl, or trifluoromethylsulfonyl; R ^2b being chlorine, fluorine, bromine, iodine, difluoromethyl, trifluoromethyl, trifluoromethylsulfanyl, trifluoromethylsulfonyl; R ³ being methyl or hydrogen.

J. the compound of formula I corresponds to a compound of formula l-X with X being O, Y being a direct bond or CH2, Q ¹ -Q ² being one of Q ¹ -1 to Q ¹ -33, wherein Q ² is represented by Q ² -1 to Q ² -26, A ¹ and A ² being, independently from each other, CH or N; R ¹ being hydrogen, methyl, propargyl or cyclopropyl-methyl; R ^2a being trifluoromethyl, fluorine, chlorine, or bromine; and R ^2b being fluorine, chlorine or trifluoromethyl; R ³ methyl. In preferred embodiments of each aspect of the invention, Q ¹ -Q ² is represented by one of Q ¹ -1 , Q ¹ -3, Q ¹ -7, Q ¹ -9, Q ¹ -13, Q ¹ 15, Q ¹ -18, Q ¹ -19, Q ¹ -21 and Q ¹ -25; and/or Q ² is represented by one of Q ² -1 , Q ² -2, Q ² -4, Q ² -9 and Q ² -10; and/or L is represented by one of L-1 , L-2, L-3, L-4, L-5, L-6, L-7, L-8 and L-9; and/or R ³ is H; and/or Y is CH ₂ .

In addition, compounds of formula I which have at least one basic centre can form, for example, acid addition salts, for example with strong inorganic acids such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphorus acid or a hydrohalic acid, with strong organic carboxylic acids, such as C ₁ -C ₄ alkanecarboxylic acids which are unsubstituted or substituted, for example by halogen, for example acetic acid, such as saturated or unsaturated dicarboxylic acids, for example oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, such as hydroxycarboxylic acids, for example ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or such as benzoic acid, or with organic sulfonic acids, such as C ₁ -C ₄ alkane- or arylsulfonic acids which are unsubstituted or substituted, for example by halogen, for example methane- or p-toluenesulfonic acid. Compounds of formula I which have at least one acidic group can form, for example, salts with bases, for example mineral salts such as alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono- di- or tri-lower-alkylamine, for example ethyl-, diethyl-, triethyl- or dimethylpropylamine, or a mono-, di- or trihydroxy-lower-alkylamine, for example mono-, di- or triethanolamine.

In each case, the compounds of formula I according to the invention are in free form, in oxidized form as a N-oxide or in salt form, e.g. an agronomically usable salt form.

N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen containing heteroaromatic compounds. They are described for instance in the book “Heterocyclic N-oxides” by A. Albini and S. Pietra, CRC Press, Boca Raton 1991.

The compounds according to the first aspect of the invention also include hydrates which may be formed during the salt formation.

In each aspect of the present invention, the compounds of formula I may contain a stereogenic centre which is indicated with an asterisk in the structure below: wherein Q ¹ , Q ² , X, Y, R ¹ , R ³ and L are each as defined in the above embodiments. The present invention contemplates both racemates and individual enantiomers of the compound of formula I. In particular, the individual enantiomers correspond to the following structures: wherein Q ¹ , Q ² , X, Y, R ¹ , R ³ and L are as defined as in the above embodiments.

In a preferred embodiment of the invention, in which L is represented by the below structure the compound may contain a stereogenic centre which is indicated with an asterisk in the structure below, and the individual enantiomers correspond to the below structures: wherein Q ¹ , Q ² , X, Y, R ¹ , R ³ , A ¹ , A ² , R ^2a and R ^2b are as defined above.

Preparation of compounds of formula I

The compounds of formula I according to the first aspect of the invention can be produced by methods known to those skilled in the art. The skilled person will appreciate that adaptation of methods known in the art could be applied in the manufacture of the compounds of the present invention.

For example, the skilled person will be immediately familiar with standard textbooks such as “Comprehensive Organic Transformations - A Guide to Functional Group Transformations”, RC Larock, Wiley-VCH (1999 or later editions); “March's Advanced Organic Chemistry - Reactions, Mechanisms and Structure”, MB Smith, J. March, Wiley, (5th edition or later editions); “Advanced Organic Chemistry, Part B, Reactions and Synthesis”, FA Carey, RJ Sundberg, Kluwer Academic/Plenum Publications, (2001 or later editions); “Organic Synthesis - The Disconnection Approach”, S Warren (Wiley), (1982 or later editions); “Designing Organic Syntheses” S Warren (Wiley) (1983 or later editions); “Heterocyclic Chemistry”, J. Joule (Wiley 2010 edition or later editions); (“Guidebook To Organic Synthesis" RK Mackie and DM Smith (Longman) (1982 or later editions), etc., and the references therein as a guide.

The skilled person is familiar with a range of strategies for synthesising organic and particularly heterocyclic molecules and these represent common general knowledge as set out in text books such as Warren “Organic Synthesis: The Disconnection Approach”; Mackie and Smith “Guidebook to Organic Chemistry”; and Clayden, Greeves, Warren and Wothers “Organic Chemistry”.

The skilled person will exercise his/her judgement and skill as to the most efficient sequence of reactions for the synthesis of a given target compound and will employ protecting groups as necessary. This will depend inter alia on factors such as the nature of other functional groups present in a particular substrate. Clearly, the type of chemistry involved will influence the choice of reagent that is used in the said synthetic steps, the need, and type, of protecting groups that are employed, and the sequence for accomplishing the protection/deprotection steps. These and other reaction parameters will be evident to the skilled person by reference to standard textbooks and to the examples provided herein.

Sensitive functional groups may need to be protected and deprotected during synthesis of a compound of the invention. This may be achieved by conventional methods using protecting groups (sometimes abbreviated as “PG” hereinafter), for example as described in “Protective Groups in Organic Synthesis” by TW Greene and PGM Wuts, John Wiley & Sons Inc. (1999), and references therein.

For example, compounds of formula I can be made, for example, as shown in scheme 1 .

Compounds of formula I can be made, for example, as shown in scheme 2.

Compounds of formula I can be made, for example, as shown in scheme 3.

Compounds of formula I can be made, for example, as shown in scheme 4. Compounds of formula I can be made, for example, as shown in scheme 5.

Compounds of formula I can be made, for example, as shown in scheme 6. Compounds of formula I can be made, for example, as shown in scheme 7.

X: Br, I

Compounds of formula I can be made, for example, as shown in scheme 8.

X: F, Cl

A ⁶ : CH or N Compounds of formula I can be made, for example, as shown in scheme 9.

A ⁶ : CH or N

Compounds of formula I can be made, for example, as shown in scheme 10.

X: Cl, Br. I. OMs, OTs, OTf

Compounds of formula I can be made, for example, as shown in scheme 11 .

X: Cl, Br. I. OMs, OTs, OTf Compounds of formula I can be made, for example, as shown in scheme 12.

Compounds of formula I can be made, for example, as shown in scheme 13.

Compounds of formula I can be made, for example, as shown in scheme 14.

Compounds of formula I can be made, for example, as shown in scheme 15.

Compounds of formula I can be made, for example, as shown in scheme 16.

X: Cl, Br. I

Compounds of formula I can be made, for example, as shown in scheme 17.

X: Cl, Br. I

Compounds of formula I can be made, for example, as shown in scheme 18.

Compounds of formula I can be made, for example, as shown in scheme 19.

Compounds of formula I can be made, for example, as shown in scheme 20.

Compounds of formula I can be made, for example, as shown in scheme 21 .

Compounds of formula I can be made, for example, as shown in scheme 22.

Compounds of formula I can be made, for example, as shown in scheme 23. ‘First step done as described in WO2021083936 It is advantageous to isolate or synthesize in each case the biologically more effective isomer, for example enantiomer or diastereomer, or isomer mixture, for example enantiomer mixture or diastereomer mixture, if the individual components have a different biological activity. The compounds of formula I and, where appropriate, the tautomers thereof, in each case in free form or in salt form, can, if appropriate, also be obtained in the form of hydrates and/or include other solvents, for example those which may have been used for the crystallization of compounds which are present in solid form.

In the fifth aspect, the present invention also relates to novel compounds which are intermediates in the preparation of the compound according to formula I. In an exemplary embodiment, the invention therefore provides compounds having the following structures:

In another aspect of the invention, it is provided the use of any of the above intermediate compounds in the preparation of a compound according to the first aspect of the invention and it is further provided a process for preparing a compound according to the first aspect of the invention involving any of the above intermediate compounds.

In the sixth of the invention compounds with improved human and environmentally profiles compared to other products used to control insect pests and/or pests of the order Acarina in certain crops are provided.

Compositions comprising a compound of formula I

The compounds according to the first aspect of the invention can be used as in unmodified form, but they may also be formulated into compositions in various ways using formulation adjuvants, such as carriers, solvents and surface-active substance.

Therefore, in the second aspect of the invention, it is provided a composition comprising a compound of formula I as defined in any of the above embodiments relating to the first aspect of the invention, one or more auxiliary and/or adjuvant, and optionally one or more other active ingredients.

The compositions can be in various physical forms, e.g. in the form of dusting powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, oil-flowables, aqueous dispersions, oily dispersions, suspo-emulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (with water or a water-miscible organic solvent as carrier), impregnated polymer films or in other forms known e.g. from the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, First Edition, Second Revision (2010). Such compositions can either be used directly or diluted prior to use. The dilutions can be made, for example, with water, liquid fertilisers, micronutrients, biological organisms, oil or solvents.

The compositions according to the second aspect of the invention are prepared in a known manner, by mixing the compounds of the formula I with the one or more adjuvants, and optionally one or more other active ingredients. In addition, the composition may comprise further additives that are conventional in this technical field, including but not limited to colorants, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins and water.

For example, the compositions can be prepared e.g. by mixing a compound according the first aspect of the present invention as the active ingredient with the adjuvant(s) in order to obtain compositions in the form of finely divided solids, granules, solutions, dispersions or emulsions. The active ingredients can also be formulated with other adjuvants, such as finely divided solids, mineral oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surface-active substances or combinations thereof. The active ingredients can also be contained in very fine microcapsules. Microcapsules contain the active ingredients in a porous carrier. This enables the active ingredients to be released into the environment in controlled amounts (e.g. slow-release).

Microcapsules usually have a diameter of from 0.1 to 500 microns. They contain active ingredients in an amount of about from 25 to 95 % by weight of the capsule weight. The active ingredients can be in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution. The encapsulating membranes can comprise, for example, natural or synthetic rubbers, cellulose, styrene/butadiene copolymers, polyacrylonitrile, polyacrylate, polyesters, polyamides, polyureas, polyurethane or chemically modified polymers and starch xanthates or other polymers that are known to the person skilled in the art. Alternatively, very fine microcapsules can be formed in which the active ingredient is contained in the form of finely divided particles in a solid matrix of base substance, but the microcapsules are not themselves encapsulated. (a) Adjuvants

The adjuvants that are suitable for the preparation of the compositions according to the second aspect of the present invention are known in this technical field.

As liquid carriers there may be used: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1 ,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1 ,4- dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1 ,1 ,1 -trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxy-propanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m- xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol, propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, and alcohols of higher molecular weight, such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone and the like.

Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar substances.

A large number of surface-active substances can be used in both solid and liquid formulations, especially in those formulations which can be diluted with a carrier prior to use. Surface-active substances may be anionic, cationic, non-ionic or polymeric and they can be used as emulsifiers, wetting agents or suspending agents or for other purposes. Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol/alkylene oxide addition products, such as nonylphenol ethoxylate; alcohol/alkylene oxide addition products, such as tridecylalcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryltrimethylammonium chloride, polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and di-alkylphosphate esters; and also further substances described e.g. in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood New Jersey (1981 ).

Further adjuvants that can be used in pesticidal formulations include crystallisation inhibitors, viscosity modifiers, suspending agents, dyes, anti-oxidants, foaming agents, light absorbers, mixing auxiliaries, antifoams, complexing agents, neutralising or pH-modifying substances and buffers, corrosion inhibitors, fragrances, wetting agents, take-up enhancers, micronutrients, plasticisers, glidants, lubricants, dispersants, thickeners, antifreezes, microbicides, and liquid and solid fertilisers.

The compositions according to the second aspect of the present invention can further include an additive comprising an oil of vegetable or animal origin, a mineral oil, alkyl esters of such oils or mixtures of such oils and oil derivatives. The amount of oil additive in the composition according to the invention is generally from 0.01 to 10 %, based on the mixture to be applied. For example, the oil additive can be added to a spray tank in the desired concentration after a spray mixture has been prepared. Preferred oil additives comprise mineral oils or an oil of vegetable origin, for example rapeseed oil, olive oil or sunflower oil, emulsified vegetable oil, alkyl esters of oils of vegetable origin, for example the methyl derivatives, or an oil of animal origin, such as fish oil or beef tallow. Preferred oil additives comprise alkyl esters of C ₈ -C ₂₂ fatty acids, especially the methyl derivatives of C ₁₂ -C ₁₈ fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid (methyl laurate, methyl palmitate and methyl oleate, respectively). Many oil derivatives are known from the Compendium of Herbicide Adjuvants, 10 ^{t h} Edition, Southern Illinois University, 2010.

The inventive compositions generally comprise from 0.1 to 99 % by weight, especially from 0.1 to 95 % by weight, of compounds of the present invention and from 1 to 99.9 % by weight of a formulation adjuvant which preferably includes from 0 to 25 % by weight of a surface-active substance.

Formulation types for the composition of the invention include an emulsion concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP), a soluble granule (SG) or any technically feasible formulation in combination with agriculturally acceptable adjuvants. Whereas commercial products may preferably be formulated as concentrates, the end user will normally employ dilute formulations.

The rates of application vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the pest to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop. As a general guideline compounds may be applied at a rate of from 1 to 2000 l/ha, especially from 10 to 1000 l/ha.

Preferred formulations can have the following compositions (% refers to weight % unless otherwise indicated), wherein “active ingredient” refers to the compounds of the present invention:

(1) Emulsifiable concentrates: active ingredient: 1 to 95 %, preferably 20 to 80 % surface-active agent: 1 to 30 %, preferably 5 to 20 % liquid carrier: 1 to 80 %, preferably 1 to 35 %

(2) Dusts: active ingredient: 0.1 to 10 %, preferably 0.1 to 5 % solid carrier: 99.9 to 90 %, preferably 99.9 to 99 %

(3) Suspension concentrates: active ingredient: 5 to 75 %, preferably 10 to 50 % water: 94 to 24 %, preferably 88 to 30 % surface-active agent: 1 to 40 %, preferably 2 to 30 %

(4) Wettable powders: active ingredient: 0.5 to 90 %, preferably 1 to 80 % surface-active agent: 0.5 to 20 %, preferably 1 to 15 % solid carrier: 5 to 95 %, preferably 15 to 90 %

(5) Granules: active ingredient: 0.1 to 30 %, preferably 0.1 to 15 % solid carrier: 99.5 to 70 %, preferably 97 to 85 %.

(b) Other active ingredients

The activity of the compositions according to the second aspect of the present invention can be broadened considerably, and adapted to prevailing circumstances, by adding other insecticidally, acaricidally and/or fungicidally active ingredients. The mixtures of the compounds of formula I with other insecticidally, acaricidally and/or fungicidally active ingredients may also have further surprising advantages which can also be described, in a wider sense, as synergistic activity. For example, better tolerance by plants, reduced phytotoxicity, insects can be controlled in their different development stages or better behaviour during their production, for example during grinding or mixing, during their storage or during their use. Therefore, the composition according to the second aspect of the present invention may further contain one or more other active ingredients.

Suitable other active ingredients here are, for example, representatives of the following classes of active ingredients: organophosphorus compounds, nitrophenol derivatives, thioureas, juvenile hormones, formamidines, benzophenone derivatives, ureas, pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acylureas, pyridylmethyleneamino derivatives, macrolides, neonicotinoids and Bacillus thuringiensis preparations.

For the compositions according to the second aspect of the invention, the mixtures of a compound according to the first aspect with one or more other active ingredients listed below are preferred: substances consisting of petroleum oils (628); an insect control active substance selected from Abamectin, Acequinocyl, Acetamiprid, Acetoprole, Acrinathrin, Acynonapyr, Afidopyropen, Afoxolaner, Alanycarb, Allethrin, Alpha-Cypermethrin, Alphamethrin, Amidoflumet, Aminocarb, Azocyclotin, Bensultap, Benzoximate, Benzpyrimoxan, Betacyfluthrin, Beta- cypermethrin, Bifenazate, Bifenthrin, Binapacryl, Bioallethrin, Bioallethrin S)- cyclopentylisomer, Bioresmethrin, Bistrifluron, Broflanilide, Brofluthrinate, Bromophos-ethyl, Buprofezine, Butocarboxim, Cadusafos, Carbaryl, Carbosulfan, Cartap, CAS number: 1632218-00-8, CAS number: 1808115-49-2, CAS number: 2032403-97-5, CAS number: 2044701-44-0, CAS number: 2128706-05-6, CAS number: 2246757-58-2 (or 2249718-27-0), CAS number: 907187-07-9, Chlorantraniliprole, Chlordane, Chlorfenapyr, Chloroprallethrin, Chromafenozide, Clenpirin, Cloethocarb, Clothianidin, 2-chlorophenyl N-methylcarbamate (CPMC), Cyanofenphos, Cyantraniliprole, Cyclaniliprole, Cyclobutrifluram, Cycloprothrin, Cycloxaprid, Cycloxaprid, Cyenopyrafen, Cyetpyrafen, Cyflumetofen, Cyfluthrin, Cyhalodiamide, Cyhalothrin, Cypermethrin, Cyphenothrin, Cyproflanilide, Cyromazine, Deltamethrin, Diafenthiuron, Dialifos, Dibrom, Dicloromezotiaz, Diflovidazine, Diflubenzuron, dimpropyridaz, Dinactin, Dinocap, Dinotefuran, Dioxabenzofos, Emamectin (or Emamectin Benzoate), Empenthrin, Epsilon - momfluorothrin, Epsilon-metofluthrin, Esfenvalerate, Ethion, Ethiprole, Etofenprox, Etoxazole, Famphur, Fenazaquin, Fenfluthrin, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyroxymate, Fensulfothion, Fenthion, Fentinacetate, Fenvalerate, Fipronil, Flometoquin, Flonicamid, Fluacrypyrim, Fluazaindolizine, Fluazuron, Flubendiamide, Flubenzimine, Flucitrinate, Flucycloxuron, Flucythrinate, Fluensulfone, Flufenerim, Flufenprox, Flufiprole, Fluhexafon, Flumethrin, Fluopyram, Flupentiofenox, Flupyradifurone, Flupyrimin, Fluralaner, Fluvalinate, Fluxametamide, Fosthiazate, Gamma-Cyhalothrin, Gossyplure™, Guadipyr, Halofenozide, Halofenozide, Halfenprox, Heptafluthrin, Hexythiazox, Hydramethylnon, Imicyafos, Imidacloprid, Imiprothrin, Indoxacarb, lodomethane, Iprodione, Isocycloseram, Isothioate, Ivermectin, Kappa-bifenthrin, Kappa-tefluthrin, Lambda-Cyhalothrin, Lepimectin, Lufenuron, Metaflumizone, Metaldehyde, Metam, Methomyl, Methoxyfenozide, Metofluthrin, Metolcarb, Mexacarbate, Milbemectin, Momfluorothrin, Niclosamide, Nicofluprole; Nitenpyram, Nithiazine, Omethoate, Oxamyl, Oxazosulfyl, Parathion-ethyl, Permethrin, Phenothrin, Phosphocarb, Piperonylbutoxide, Pirimicarb, Pirimiphos-ethyl, Pirimiphos-methyl, Polyhedrosis virus, Prallethrin, Profenofos, Profenofos, Profluthrin, Propargite, Propetamphos, Propoxur, Prothiophos, Protrifenbute, Pyflubumide, Pymetrozine, Pyraclofos, Pyrafluprole, Pyridaben, Pyridalyl, Pyrifluquinazon, Pyrimidifen, Pyriminostrobin, Pyriprole, Pyriproxyfen, Resmethrin, Sarolaner, Selamectin, Silafluofen, Spinetoram, Spinosad, Spirodiclofen, Spiromesifen, Spiropidion, Spirotetramat, Sulfoxaflor, Tebufenozide, Tebufenpyrad, Tebupirimiphos, Tefluthrin, Temephos, Tetrachlorantraniliprole, Tetradiphon, Tetramethrin, Tetramethylfluthrin, Tetranactin, Tetraniliprole, Theta-cypermethrin, Thiacloprid, Thiamethoxam, Thiocyclam, Thiodicarb, Thiofanox, Thiometon, Thiosultap, Tioxazafen, Tolfenpyrad, Toxaphene, Tralomethrin, Transfluthrin, Triazamate, Triazophos, Trichlorfon, Trichloronate, Trichlorphon, Triflumezopyrim, Tyclopyrazoflor, Zeta-Cypermethrin, Extract of seaweed and fermentation product derived from melasse, Extract of seaweed and fermentation product derived from melasse comprising urea, amino acids, potassium and molybdenum and EDTA- chelated manganese, Extract of seaweed and fermented plant products, Extract of seaweed and fermented plant products comprising phytohormones, vitamins, EDTA- chelated copper, zinc, and iron, Azadirachtin, Bacillus aizawai, Bacillus chitinosporus AQ746 (NRRL Accession No B-21 618), Bacillus firmus, Bacillus kurstaki, Bacillus mycoides AQ726 (NRRL Accession No. B-21664), Bacillus pumilus (NRRL Accession No B-30087), Bacillus pumilus AQ717 (NRRL Accession No. B-21662), Bacillus sp. AQ178 (ATCC Accession No. 53522), Bacillus sp. AQ175 (ATCC Accession No. 55608), Bacillus sp. AQ177 (ATCC Accession No. 55609), Bacillus subtilis unspecified, Bacillus subtilis AQ153 (ATCC Accession No. 55614), Bacillus subtilis AQ30002 (NRRL Accession No. B-50421 ), Bacillus subtilis AQ30004 (NRRL Accession No. B- 50455), Bacillus subtilis AQ713 (NRRL Accession No. B-21661 ), Bacillus subtilis AQ743 (NRRL Accession No. B-21665), Bacillus thuringiensis AQ52 (NRRL Accession No. B-21619), Bacillus thuringiensis BD#32 (NRRL Accession No B-21530), Bacillus thuringiensis subspec. kurstaki BMP 123, Beauveria bassiana, D- limonene, Granulovirus, Harpin, Helicoverpa armigera Nucleopolyhedrovirus, Helicoverpa zea Nucleopolyhedrovirus, Heliothis virescens Nucleopolyhedrovirus, Heliothis punctigera Nucleopolyhedrovirus, Metarhizium spp., Muscodor albus 620 (NRRL Accession No. 30547), Muscodor roseus A3-5 (NRRL Accession No. 30548), Neem tree based products, Paecilomyces fumosoroseus, Paecilomyces lilacinus, Pasteuria nishizawae, Pasteuria penetrans, Pasteuria ramosa, Pasteuria thornei, Pasteuria usgae, P-cymene, Plutella xylostella Granulosis virus, Plutella xylostella Nucleopolyhedrovirus, Polyhedrosis virus, pyrethrum, QRD 420 (a terpenoid blend), QRD 452 (a terpenoid blend), QRD 460 (a terpenoid blend), Quillaja saponaria, Rhodococcus globerulus AQ719 (NRRL Accession No B-21663), Spodoptera frugiperda Nucleopolyhedrovirus, Streptomyces galbus (NRRL Accession No. 30232), Streptomyces sp. (NRRL Accession No. B-30145), Terpenoid blend, and Verticillium spp.; an algicide selected from the group of substances consisting of bethoxazin [CCN], copper dioctanoate (170), copper sulfate (172), cybutryne [CCN], dichlone (1052), dichlorophen (232), endothal (295), fentin (347), hydrated lime [CCN], nabam (566), quinoclamine (714), quinonamid (1379), simazine (730), triphenyltin acetate (347) and triphenyltin hydroxide (347); an anthelmintic selected from the group of substances consisting of abamectin (1 ), crufomate (1011 ), Cyclobutrifluram, doramectin [CCN], emamectin (291 ), emamectin benzoate (291), eprinomectin [CCN], ivermectin [CCN], milbemycin oxime [CCN], moxidectin [CCN], piperazine [CCN], selamectin [CCN], spinosad (737) and thiophanate (1435); an avicide selected from the group of substances consisting of chloralose (127), endrin (1122), fenthion (346), pyridin-4-amine (23) and strychnine (745); a bactericide selected from the group of substances consisting of 1 -hydroxy-1 H- pyridine-2-thione (1222), 4-(quinoxalin-2-ylamino)benzenesulfonamide (748), 8- hydroxyquinoline sulfate (446), bronopol (97), copper dioctanoate (170), copper hydroxide (169), cresol [CCN], dichlorophen (232), dipyrithione (1105), dodicin (1112), fenaminosulf (1144), formaldehyde (404), hydrargaphen [CCN], kasugamycin (483), kasugamycin hydrochloride hydrate (483), nickel bis(dimethyldithiocarbamate) (1308), nitrapyrin (580), octhilinone (590), oxolinic acid (606), oxytetracycline (611 ), potassium hydroxyquinoline sulfate (446), probenazole (658), streptomycin (744), streptomycin sesquisulfate (744), tecloftalam (766), and thiomersal [CCN]; a biological agent selected from the group of substances consisting of Adoxophyes orana GV (12), Agrobacterium radiobacter (13), Amblyseius spp. (19), Anagrapha falcifera NPV (28), Anagrus atomus (29), Aphelinus abdominalis (33), Aphidius colemani (34), Aphidoletes aphidimyza (35), Autographa californica NPV (38), Bacillus firmus (48), Bacillus sphaericus Neide (49), Bacillus thuringiensis Berliner (51 ), Bacillus thuringiensis subsp. aizawai (51), Bacillus thuringiensis subsp. israelensis (51 ), Bacillus thuringiensis subsp. japonensis (51 ), Bacillus thuringiensis subsp. kurstaki (51), Bacillus thuringiensis subsp. tenebrionis (51), Beauveria bassiana (53), Beauveria brongniartii (54), Chrysoperla carnea (151 ), Cryptolaemus montrouzieri (178), Cydia pomonella GV (191), Dacnusa sibirica (212), Diglyphus isaea (254), Encarsia formosa (293), Eretmocerus eremicus (300), Helicoverpa zea NPV (431 ), Heterorhabditis bacteriophora and H. megidis (433), Hippodamia convergens (442), Leptomastix dactylopii (488), Macrolophus caliginosus (491 ), Mamestra brassicae NPV (494), Metaphycus helvolus (522), Metarhizium anisopliae var. acridum (523), Metarhizium anisopliae var. anisopliae (523), Neodiprion sertifer NPV and N. lecontei NPV (575), Orius spp.

(596), Paecilomyces fumosoroseus (613), Phytoseiulus persimilis (644), Spodoptera exigua multicapsid nuclear polyhedrosis virus (741 ), Steinernema bibionis (742), Steinernema carpocapsae (742), Steinernema feltiae (742), Steinernema glaseri (742), Steinernema riobrave (742), Steinernema riobravis (742), Steinernema scapterisci (742), Steinernema spp. (742), Trichogramma spp. (826), Typhlodromus occidentalis (844) and Verticillium lecanii (848); a soil sterilant selected from the group of substances consisting of iodomethane (542) and methyl bromide (537); a chemosterilant selected from the group of substances consisting of apholate [CCN], bisazir [CCN], busulfan [CCN], diflubenzuron (250), dimatif [CCN], hemel [CCN], hempa [CCN], metepa [CCN], methiotepa [CCN], methyl apholate [CCN], morzid [CCN], penfluron [CCN], tepa [CCN], thiohempa [CCN], thiotepa [CCN], tretamine [CCN] and uredepa [CCN]; an insect pheromone selected from the group of substances consisting of (E)-dec-5- en-1 -yl acetate with (E)-dec-5-en-1-ol (222), (E)-tridec-4-en-1-yl acetate (829), (E)- 6-methylhept-2-en-4-ol (541), (E,Z)-tetradeca-4,10-dien-1-yl acetate (779), (Z)- dodec-7-en-1-yl acetate (285), (Z)-hexadec-l 1 -enal (436), (Z)-hexadec-l 1 -en-1 -yl acetate (437), (Z)-hexadec-l 3-en-11-yn-1-yl acetate (438), (Z)-icos-13-en-10-one (448), (Z)-tetradec-7-en-1-al (782), (Z)-tetradec-9-en-1 -ol (783), (Z)-tetradec-9-en-1 - yl acetate (784), (7E,9Z)-dodeca-7,9-dien-1-yl acetate (283), (9Z, 11 E)-tetradeca- 9,11-dien-1-yl acetate (780), (9Z,12E)-tetradeca-9,12-dien-1-yl acetate (781), 14- methyloctadec-1-ene (545), 4-methylnonan-5-ol with 4-methylnonan-5-one (544), alpha-multistriatin [CCN], brevicomin [CCN], codlelure [CCN], codlemone (167), cuelure (179), disparlure (277), dodec-8-en-1-yl acetate (286), dodec-9-en-1 -yl acetate (287), dodeca-8, 10-dien-1-yl acetate (284), dominicalure [CCN], ethyl 4- methyloctanoate (317), eugenol [CCN], frontalin [CCN], gossyplure (420), grandlure (421 ), grandlure I (421 ), grandlure II (421), grandlure III (421), grandlure IV (421 ), hexalure [CCN], ipsdienol [CCN], ipsenol [CCN], japonilure (481), lineatin [CCN], litlure [CCN], looplure [CCN], medlure [CCN], megatomoic acid [CCN], methyl eugenol (540), muscalure (563), octadeca-2,13-dien-1-yl acetate (588), octadeca-3,13-dien-1-yl acetate (589), orfralure [CCN], oryctalure (317), ostramone [CCN], siglure [CCN], sordidin (736), sulcatol [CCN], tetradec-11 -en-1-yl acetate (785), trimedlure (839), trimedlure A (839), trimedlure B1 (839), trimedlure B2 (839), trimedlure C (839) and trunc-call [CCN]; an insect repellent selected from the group of substances consisting of 2- (octylthio)ethanol (591), butopyronoxyl (933), butoxy(polypropylene glycol) (936), dibutyl adipate (1046), dibutyl phthalate (1047), dibutyl succinate (1048), diethyltoluamide [CCN], dimethyl carbate [CCN], dimethyl phthalate [CCN], ethyl hexanediol (1137), hexamide [CCN], methoquin-butyl (1276), methylneodecanamide [CCN], oxamate [CCN] and picaridin [CCN]; a molluscicide selected from the group of substances consisting of bis(tributyltin) oxide (913), bromoacetamide [CCN], calcium arsenate [CCN], cloethocarb (999), copper acetoarsenite [CCN], copper sulfate (172), fentin (347), ferric phosphate (352), metaldehyde (518), methiocarb (530), niclosamide (576), niclosamide-olamine (576), pentachlorophenol (623), sodium pentachlorophenoxide (623), tazimcarb (1412), thiodicarb (799), tributyltin oxide (913), trifenmorph (1454), trimethacarb (840), triphenyltin acetate (347) and triphenyltin hydroxide (347), pyriprole [394730- 71-3]; a nematicide selected from the group of substances consisting of AKD-3088 (compound code), 1 ,2-dibromo-3-chloropropane (IIIPAC/Chemical Abstracts name) (1045), 1 ,2-dichloropropane (IIIPAC/ Chemical Abstracts name) (1062), 1 ,2- dichloropropane with 1 ,3-dichloropropene (1063), 1 ,3-dichloropropene (233), 3,4- dichlorotetrahydrothiophene 1 ,1 -dioxide (IIIPAC/Chemical Abstracts name) (1065), 3-(4-chlorophenyl)-5-methylrhodanine (980), 5-methyl-6-thioxo-1 ,3,5-thiadiazinan-3- ylacetic acid (1286), 6-isopentenylaminopurine (210), abamectin (1 ), acetoprole [CCN], alanycarb (15), aldicarb (16), aldoxycarb (863), AZ 60541 (compound code), benclothiaz [CCN], benomyl (62), butylpyridaben , cadusafos (109), carbofuran (118), carbon disulfide (945), carbosulfan (119), chloropicrin (141), chlorpyrifos (145), cloethocarb (999), Cyclobutrifluram, cytokinins (210), dazomet (216), DBCP (1045), DCIP (218), diamidafos (1044), dichlofenthion (1051), dicliphos , dimethoate (262), doramectin [CCN], emamectin (291 ), emamectin benzoate (291 ), eprinomectin [CCN], ethoprophos (312), ethylene dibromide (316), fenamiphos (326), fen pyrad , fensulfothion (1158), fosthiazate (408), fosthietan (1196), furfural [CCN], GY-81 (development code) (423), heterophos [CCN], iodomethane (542), isamidofos (1230), isazofos (1231), ivermectin [CCN], kinetin (210), mecarphon (1258), metam (519), metam-potassium (519), metam-sodium (519), methyl bromide (537), methyl isothiocyanate (543), milbemycin oxime [CCN], moxidectin [CCN], Myrothecium verrucaria composition (565), NC-184, oxamyl (602), phorate (636), phosphamidon (639), phosphocarb [CCN], sebufos , selamectin [CCN], spinosad (737), terbam , terbufos (773), tetrachlorothiophene (IIIPAC/ Chemical Abstracts name) (1422), thiafenox , thionazin (1434), triazophos (820), triazuron , xylenols [CCN], YI-5302 (compound code) and zeatin (210), fluensulfone [318290-98-1], fluopyram; a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580); a plant activator selected from the group of substances consisting of acibenzolar (6), acibenzolar-S-methyl (6), probenazole (658) and Reynoutria sachalinensis extract (720); a rodenticide selected from the group of substances consisting of 2-isovalerylindan- 1 , 3-dione (1246), 4-(quinoxalin-2-ylamino)benzenesulfonamide (748), alphachlorohydrin [CCN], aluminium phosphide (640), antu (880), arsenous oxide (882), barium carbonate (891 ), bisthiosemi (912), brodifacoum (89), bromadiolone (including alpha-bromadiolone), bromethalin (92), calcium cyanide (444), chloralose (127), chlorophacinone (140), cholecalciferol (850), coumachlor (1004), coumafuryl (1005), coumatetralyl (175), crimidine (1009), difenacoum (246), difethialone (249), diphacinone (273), ergocalciferol (301 ), flocoumafen (357), fluoroacetamide (379), flupropadine (1183), flupropadine hydrochloride (1183), gamma-HCH (430), HCH (430), hydrogen cyanide (444), iodomethane (542), lindane (430), magnesium phosphide (640), methyl bromide (537), norbormide (1318), phosacetim (1336), phosphine (640), phosphorus [CCN], pindone (1341), potassium arsenite [CCN], pyrinuron (1371 ), scilliroside (1390), sodium arsenite [CCN], sodium cyanide (444), sodium fluoroacetate (735), strychnine (745), thallium sulfate [CCN], warfarin (851 ) and zinc phosphide (640); a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl piperonylate (934), 5-(1 ,3-benzodioxol-5-yl)-3- hexylcyclohex-2-enone (903), farnesol with nerolidol (324), MB-599 (development code) (498), MGK 264 (development code) (296), piperonyl butoxide (649), pi protal (1343), propyl isomer (1358), S421 (development code) (724), sesamex (1393), sesasmolin (1394) and sulfoxide (1406); an animal repellent selected from the group of substances consisting of anthraquinone (32), chloralose (127), copper naphthenate [CCN], copper oxychloride (171 ), diazinon (227), dicyclopentadiene (chemical name) (1069), guazatine (422), guazatine acetates (422), methiocarb (530), pyridin-4-amine (23), thiram (804), trimethacarb (840), zinc naphthenate [CCN] and ziram (856); a virucide selected from the group of substances consisting of imanin [CCN] and ribavirin [CCN]; a wound protectant selected from the group of substances consisting of mercuric oxide (512), octhilinone (590) and thiophanate-methyl (802); a biologically active substance selected from 1 ,1-bis(4-chloro-phenyl)-2- ethoxyethanol, 2,4-dichlorophenyl benzenesulfonate, 2-fluoro-N-methyl-N-1- naphthylacetamide, 4-chlorophenyl phenyl sulfone, acetoprole, aldoxycarb, amidithion, amidothioate, amiton, amiton hydrogen oxalate, amitraz, aramite, arsenous oxide, azobenzene, azothoate, benomyl, benoxa-fos, benzyl benzoate, bixafen, brofenvalerate, bromo-cyclen, bromophos, bromopropylate, buprofezin, butocarboxim, butoxycarboxim, butylpyridaben, calcium polysulfide, camphechlor, carbanolate, carbophenothion, cymiazole, chino-methionat, chlorbenside, chlordimeform, chlordimeform hydrochloride, chlorfenethol, chlorfenson, chlorfensulfide, chlorobenzilate, chloromebuform, chloromethiuron, chloropropylate, chlorthiophos, cinerin I, cinerin II, cinerins, closantel, coumaphos, crotamiton, crotoxyphos, cufraneb, cyanthoate, DCPM, DDT, demephion, demephion-O, demephion-S, demeton-methyl, demeton-O, demeton-O-methyl, demeton-S, demeton-S-methyl, demeton-S-methylsulfon, dichlofluanid, dichlorvos, dicliphos, dienochlor, dimefox, dinex, dinex-diclexine, dinocap-4, dinocap-6, dinocton, dinopenton, dinosulfon, dinoterbon, dioxathion, diphenyl sulfone, disulfiram, DNOC, dofenapyn, doramectin, endothion, eprinomectin, ethoate-methyl, etrimfos, fenazaflor, fenbutatin oxide, fenothiocarb, fenpyrad, fen-pyroximate, fenpyrazamine, fenson, fentrifanil, flubenzimine, flucycloxuron, fluenetil, fluorbenside, FMC 1137, formetanate, formetanate hydrochloride, formparanate, gamma-HCH, glyodin, halfenprox, hexadecyl cyclopropanecarboxylate, isocarbophos, jasmolin I, jasmolin II, jodfenphos, lindane, malonoben, mecarbam, mephosfolan, mesulfen, methacrifos, methyl bromide, metolcarb, mexacarbate, milbemycin oxime, mipafox, monocrotophos, morphothion, moxidectin, naled, 4-chloro-2-(2-chloro-2-methyl- propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one, nifluridide, nikkomycins, nitrilacarb, nitrilacarb 1 :1 zinc chloride complex, omethoate, oxydeprofos, oxydisulfoton, pp'-DDT, parathion, permethrin, phenkapton, phosalone, phosfolan, phosphamidon, polychloroterpenes, polynactins, proclonol, promacyl, propoxur, prothidathion, prothoate, pyrethrin I, pyrethrin II, pyrethrins, pyridaphenthion, pyrimitate, quinalphos, quintiofos, R-1492, phosglycin, rotenone, schradan, sebufos, selamectin, sophamide, SSI-121 , sulfiram, sulfluramid, sulfotep, sulfur, diflovidazin, tau-fluvalinate, TEPP, terbam, tetradifon, tetrasul, thiafenox, thiocarboxime, thiofanox, thiometon, thioquinox, thuringiensin, triamiphos, triarathene, triazophos, triazuron, trifenofos, trinactin, vamidothion, vaniliprole, bethoxazin, copper dioctanoate, copper sulfate, cybutryne, dichlone, dichlorophen, endothal, fentin, hydrated lime, nabam, quinoclamine, quinonamid, simazine, triphenyltin acetate, triphenyltin hydroxide, crufomate, piperazine, thiophanate, chloralose, fenthion, pyridin-4-amine, strychnine, 1 -hydroxy-1 H-pyridine-2-thione, 4-(quinoxalin-2- ylamino)benzenesulfonamide, 8-hydroxyquinoline sulfate, bronopol, copper hydroxide, cresol, dipyrithione, dodicin, fenaminosulf, formaldehyde, hydrargaphen, kasugamycin, kasugamycin hydrochloride hydrate, nickel bis(dimethyldithiocarbamate), nitrapyrin, octhilinone, oxolinic acid, oxytetracycline, potassium hydroxyquinoline sulfate, probenazole, streptomycin, streptomycin sesquisulfate, tecloftalam, thiomersal, Adoxophyes orana GV, Agrobacterium radiobacter, Amblyseius spp., Anagrapha falcifera NPV, Anagrus atomus, Aphelinus abdominalis, Aphidius colemani, Aphidoletes aphidimyza, Autographa californica NPV, Bacillus sphaericus Neide, Beauveria brongniartii, Chrysoperla carnea, Cryptolaemus montrouzieri, Cydia pomonella GV, Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Eretmocerus eremicus, Heterorhabditis bacteriophora and H. megidis, Hippodamia convergens, Leptomastix dactylopii, Macrolophus caliginosus, Mamestra brassicae NPV, Metaphycus helvolus, Metarhizium anisopliae var. acridum, Metarhizium anisopliae var. anisopliae, Neodiprion sertifer NPV and N. lecontei NPV, Orius spp., Paecilomyces fumosoroseus, Phytoseiulus persimilis, Steinernema bibionis, Steinernema carpocapsae, Steinernema feltiae, Steinernema glaseri, Steinernema riobrave, Steinernema riobravis, Steinernema scapterisci, Steinernema spp., Trichogramma spp., Typhlodromus occidentalis , Verticillium lecanii, apholate, bisazir, busulfan, dimatif, hemel, hempa, metepa, methiotepa, methyl apholate, morzid, penfluron, tepa, thiohem pa, thiotepa, tretamine, uredepa, (E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol, (E)-tridec-4-en-1-yl acetate, (E)-6- methylhept-2-en-4-ol, (E,Z)-tetradeca-4,10-dien-1 -yl acetate, (Z)-dodec-7-en-1-yl acetate, (Z)-hexadec-l 1-enal, (Z)-hexadec-l 1-en-1-yl acetate, (Z)-hexadec-l 3-en-11 -yn-1-yl acetate, (Z)-icos-13-en-10-one, (Z)-tetradec-7-en-1-al, (Z)-tetradec-9-en-1-ol, (Z)-tetradec-9-en-1 -yl acetate, (7E,9Z)-dodeca-7,9-dien-1-yl acetate, (9Z,11 E)- tetradeca-9,11 -dien-1 -yl acetate, (9Z,12E)-tetradeca-9,12-dien-1-yl acetate, 14- methyloctadec-1-ene, 4-methylnonan-5-ol with 4-methylnonan-5-one, alpha- multistriatin, brevicomin, codlelure, codlemone, cuelure, disparlure, dodec-8-en-1 -yl acetate, dodec-9-en-1 -yl acetate, dodeca-8, 10-dien-1 -yl acetate, dominicalure, ethyl 4-m ethyloctanoate, eugenol, frontalin, grandlure, grandlure I, grandlure II, grandlure III, grandlure IV, hexalure, ipsdienol, ipsenol, japonilure, lineatin, litlure, looplure, medlure, megatomoic acid, methyl eugenol, muscalure, octadeca-2,13-dien-1-yl acetate, octadeca-3,13-dien-1 -yl acetate, orfralure, oryctalure, ostramone, siglure, sordidin, sulcatol, tetradec-11 -en-1-yl acetate, trimedlure, trimedlure A, trimedlure B1 , trimedlure B2, trimedlure C, trunc-call, 2-(octylthio)-ethanol, butopyronoxyl, butoxy(polypropylene glycol), dibutyl adipate, dibutyl phthalate, dibutyl succinate, diethyltoluamide, dimethyl carbate, dimethyl phthalate, ethyl hexanediol, hexamide, methoquin-butyl, methylneodecanamide, oxamate, picaridin, 1-dichloro-1- nitroethane, 1 ,1-dichloro-2,2-bis(4-ethylphenyl)-ethane, 1 ,2-dichloropropane with 1 ,3- dichloropropene, 1 -bromo-2 -chloroethane, 2 , 2, 2-trichloro-1 -(3,4-dichloro-phenyl)ethyl acetate, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate, 2-(1 ,3-dithiolan-2- yl)phenyl dimethylcarbamate, 2-(2-butoxyethoxy)ethyl thiocyanate, 2-(4,5-dimethyl- 1 ,3-dioxolan-2-yl)phenyl methylcarbamate, 2-(4-chloro-3,5-xylyloxy)ethanol, 2- chlorovinyl diethyl phosphate, 2-imidazolidone, 2-isovalerylindan-1 ,3-dione, 2- methyl(prop-2-ynyl)aminophenyl methylcarbamate, 2-thiocyanatoethyl laurate, 3- bromo-1-chloroprop-1-ene, 3-methyl-1 -phenylpyrazol-5-yl dimethyl-carbamate, 4- methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate, 5,5-dimethyl-3-oxocyclohex-1 - enyl dimethylcarbamate, acethion, acrylonitrile, aldrin, allosamidin, allyxycarb, alphaecdysone, aluminium phosphide, aminocarb, anabasine, athidathion, azamethiphos, Bacillus thuringiensis delta endotoxins, barium hexafluorosilicate, barium polysulfide, barthrin, Bayer 22/190, Bayer 22408, beta-cyfluthrin, beta-cypermethrin, bioethanomethrin, biopermethrin, bis(2-chloroethyl) ether, borax, bromfenvinfos, bromo-DDT, bufencarb, butacarb, butathiofos, butonate, calcium arsenate, calcium cyanide, carbon disulfide, carbon tetrachloride, cartap hydrochloride, cevadine, chlorbicyclen, chlordane, chlordecone, chloroform, chloropicrin, chlorphoxim, chlorprazophos, cis-resmethrin, cismethrin, clocythrin, copper acetoarsenite, copper arsenate, copper oleate, coumithoate, cryolite, CS 708, cyanofenphos, cyanophos, cyclethrin, cythioate, d-tetramethrin, DAEP, dazomet, decarbofuran, diamidafos, dicapthon, dichlofenthion, dicresyl, dicyclanil, dieldrin, diethyl 5-methylpyrazol-3-yl phosphate, dilor, dimefluthrin, dimetan, dimethrin, dimethylvinphos, dimetilan, dinoprop, dinosam, dinoseb, diofenolan, dioxabenzofos, dithicrofos, DSP, ecdysterone, El 1642, EMPC, EPBP, etaphos, ethiofencarb, ethyl formate, ethylene dibromide, ethylene dichloride, ethylene oxide, EXD, fenchlorphos, fenethacarb, fenitrothion, fenoxacrim, fenpirithrin, fensulfothion, fenthion-ethyl, flucofuron, fosmethilan, fospirate, fosthietan, furathiocarb, furethrin, guazatine, guazatine acetates, sodium tetrathiocarbonate, halfenprox, HCH, HEOD, heptachlor, heterophos, HHDN, hydrogen cyanide, hyquincarb, IPSP, isazofos, isobenzan, isodrin, isofenphos, isolane, isoprothiolane, isoxathion, juvenile hormone I, juvenile hormone II, juvenile hormone III, kelevan, kinoprene, lead arsenate, leptophos, lirimfos, lythidathion, m-cumenyl methylcarbamate, magnesium phosphide, mazidox, mecarphon, menazon, mercurous chloride, mesulfenfos, metam, metam-potassium, metam-sodium, methanesulfonyl fluoride, methocrotophos, methoprene, methothrin, methoxychlor, methyl isothiocyanate, methylchloroform, methylene chloride, metoxadiazone, mirex, naftalofos, naphthalene, NC-170, nicotine, nicotine sulfate, nithiazine, nornicotine, O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate, O,0-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate, O,0-diethyl 0-6- methyl-2-propylpyrimidin-4-yl phosphorothioate, O,O,O',O'-tetrapropyl dithiopyrophosphate, oleic acid, para-dichlorobenzene, parathion-methyl, pentachlorophenol, pentachlorophenyl laurate, PH 60-38, phenkapton, phosnichlor, phosphine, phoxim-methyl, pirimetaphos, polychlorodicyclopentadiene isomers, potassium arsenite, potassium thiocyanate, precocene I, precocene II, precocene III, primidophos, profluthrin, promecarb, prothiofos, pyrazophos, pyresmethrin, quassia, quinalphos-methyl, quinothion, rafoxanide, resmethrin, rotenone, kadethrin, ryania, ryanodine, sabadilla), schradan, sebufos, SI-0009, thiapronil, sodium arsenite, sodium cyanide, sodium fluoride, sodium hexafluorosilicate, sodium pentachlorophenoxide, sodium selenate, sodium thiocyanate, sulcofuron, sulcofuron-sodium, sulfuryl fluoride, sulprofos, tar oils, tazimcarb, TDE, tebupirimfos, temephos, terallethrin, tetrachloroethane, thicrofos, thiocyclam, thiocyclam hydrogen oxalate, thionazin, thiosultap, thiosultap-sodium, tralomethrin, transpermethrin, triazamate, trichlormetaphos-3, trichloronat, trimethacarb, tolprocarb, triclopyricarb, triprene, veratridine, veratrine, XMC, zetamethrin, zinc phosphide, zolaprofos, and meperfluthrin, tetramethylfluthrin, bis(tributyltin) oxide, bromoacetamide, ferric phosphate, niclosamide-olamine, tributyltin oxide, pyrimorph, trifenmorph, 1 ,2-dibromo-3-chloropropane, 1 ,3- dichloropropene, 3,4-dichlorotetrahydrothio-phene 1 ,1 -dioxide, 3-(4-chlorophenyl)-5- methylrhodanine, 5-methyl-6-thioxo-1 ,3,5-thiadiazinan-3-ylacetic acid, 6- isopentenylaminopurine, 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine, benclothiaz, cytokinins, DCIP, furfural, isamidofos, kinetin, Myrothecium verrucaria composition, tetrachlorothiophene, xylenols, zeatin, potassium ethylxanthate, acibenzolar, acibenzolar-S-methyl, Reynoutria sachalinensis extract, alphachlorohydrin, antu, barium carbonate, bisthiosemi, brodifacoum, bromadiolone, bromethalin, chlorophacinone, cholecalciferol, coumachlor, coumafuryl, coumatetralyl, crimidine, difenacoum, difethialone, diphacinone, ergocalciferol, flocoumafen, fluoroacetamide, flupropadine, flupropadine hydrochloride, norbormide, phosacetim, phosphorus, pindone, pyrinuron, scilliroside, -sodium fluoroacetate, thallium sulfate, warfarin, -2-(2-butoxyethoxy)ethyl piperonylate, 5-(1 ,3-benzodioxol- 5-yl)-3-hexylcyclohex-2-enone, farnesol with nerolidol, verbutin, MGK 264, piperonyl butoxide, piprotal, propyl isomer, S421 , sesamex, sesasmolin, sulfoxide, anthraquinone, copper naphthenate, copper oxychloride, dicyclopentadiene, thiram, zinc naphthenate, ziram, imanin, ribavirin, chloroinconazide, mercuric oxide, thiophanate-methyl, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furametpyr, hexaconazole, imazalil-, imiben-conazole, ipconazole, metconazole, myclobutanil, paclobutrazole, pefurazoate, penconazole, prothioconazole, pyrifenox, prochloraz, propiconazole, pyrisoxazole, -simeconazole, tebucon-azole, tetraconazole, triadimefon, triadimenol, triflum izole, triticonazole, ancymidol, fenarimol, nuarimol, bupirimate, dimethirimol, ethirimol, dodemorph, fenpropidin, fenpropimorph, spiroxamine, tridemorph, cyprodinil, mepanipyrim, pyrimethanil, fenpiclonil, fludioxonil, benalaxyl, furalaxyl, -metalaxyl, Rmetalaxyl, ofurace, oxadixyl, carbendazim, debacarb, fuberidazole, thiabendazole, chlozolinate, dichlozoline, myclozoline-, procymidone, vinclozoline, boscalid, carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, penthiopyrad, thifluzamide, dodine, iminoctadine, azoxystrobin, dimoxystrobin, enestroburin, fenaminstrobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, ferbam, mancozeb, maneb, metiram, propineb, zineb, captafol, captan, fluoroimide, folpet, tolylfluanid, bordeaux mixture, copper oxide, mancopper, oxine-copper, nitrothal-isopropyl, edifenphos, iprobenphos, phosdiphen, tolclofos-methyl, anilazine, benthiavalicarb, blasticidin-S, chloroneb, chloro-tha-lonil, cyflufenamid, cymoxanil, cyclobutrifluram, diclocymet, diclomezine, dicloran, diethofencarb, dimethomorph, flumorph, dithianon, ethaboxam, etridiazole, famoxadone, fenamidone, fenoxanil, ferimzone, fluazinam, fluopicolide, flusulfamide, fluxapyroxad, -fenhexamid, fosetyl-aluminium, hymexazol, iprovalicarb, cyazofamid, methasulfocarb, metrafenone, pencycuron, phthalide, polyoxins, propamocarb, pyribencarb, proquinazid, pyroquilon, pyriofenone, quinoxyfen, quintozene, tiadinil, triazoxide, tricyclazole, triforine, validamycin, valifenalate, zoxamide, mandipropamid, flubeneteram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, 3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide, isoflucypram, isotianil, dipymetitrone, 6- ethyl-5,7-dioxo-pyrrolo[4,5][1 ,4]dithiino[1 ,2-c]isothiazole-3-carbonitrile, 2- (difluoromethyl)-N-[3-ethyl-1 ,1 -dimethyl-indan-4-yl]pyridine-3-carboxamide, 4-(2,6- difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile, (R)-3-(difluoromethyl)-1 - methyl-N-[1 ,1 ,3-trimethylindan-4-yl]pyrazole-4-carboxamide, 4-(2-bromo-4-fluoro- phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3- amine, 4- (2- bromo- 4- fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1 ,3-dimethyl-1 H-pyrazol-5- amine, fluindapyr, coumethoxystrobin (jiaxiangjunzhi), Ivbenmixianan, dichlobentiazox, mandestrobin, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1 -yl)quinolone, 2- [2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan -2-ol, oxathiapiprolin, tertbutyl N-[6-[[[(1 -methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2- pyridyl]carbamate, pyraziflumid, inpyrfluxam, trolprocarb, mefentrifluconazole, ipfentrifluconazole, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1 , 1 -dimethyl-indan-4-yl]pyrid ine-3-carboxamide, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl- formamidine, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-e thyl-N- methyl-formamidine, [2-[3-[2-[1 -[2-[3,5-bis(difluoromethyl)pyrazol-1 -yl]acetyl]-4- piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-p henyl] methanesulfonate, but-3-ynyl N-[6-[[(Z)-[(1 -methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2- pyridyl]carbamate, methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl- phenyl]methyl]carbamate, 3-chloro-6-methyl-5-phenyl-4-(2,4,6- trifluorophenyl)pyridazine, pyridachlometyl, 3-(difluoromethyl)-1 -methyl-N-[1 ,1 ,3- trimethylindan-4-yl]pyrazole-4-carboxamide, 1 -[2-[[1 -(4-chlorophenyl)pyrazol-3- yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one, 1 -methyl-4-[3-methyl-2-[[2- methyl-4-(3,4,5-trimethylpyrazol-1 -yl)phenoxy]methyl]phenyl]tetrazol-5-one, aminopyrifen, ametoctradin, amisulbrom, penflufen, (Z,2E)-5-[1 -(4- chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pe nt-3-enamide, florylpicoxamid, fenpicoxamid, tebufloquin, ipflufenoquin, quinofumelin, isofetamid, N- [2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1 -methyl-pyrazole-4- carboxamide, N-[2-[2-ch loro-4- (trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1 - methyl-pyrazole-4-carboxamide, benzothiostrobin, phenamacril, 5-amino-1 ,3,4- thiadiazole-2-thiol zinc salt (2:1 ), fluopyram, flutianil, fluopimomide, pyrapropoyne, picarbutrazox, 2-(difluoromethyl)-N-(3-ethyl-1 , 1 -dimethyl-indan-4-yl)pyridine-3- carboxamide, 2- (difluoromethyl) -N- ((3R) - 1 , 1 , 3- trimethylindan- 4- yl) pyridine- 3- carboxamide, 4-[[6-[2-(2,4-difluorophenyl)-1 ,1 -difluoro-2-hydroxy-3-(1 ,2,4-triazol-1 - yl)propyl]-3-pyridyl]oxy]benzonitrile, metyltetraprole, 2-(difluoromethyl) - N- ((3R) - 1 , 1 , 3- trimethylindan- 4- yl) pyridine-3-carboxamide, a-(1 ,1 -dimethylethyl)-a-[4'- (trifluoromethoxy) [1 , 1 - biphenyl] - 4- yl] -5- pyrimidinemethanol, fluoxapiprolin, enoxastrobin, 4-[[6-[2-(2,4-difluorophenyl)-1 ,1 -difluoro-2-hydroxy-3-(1 ,2,4-triazol-1 - yl)propyl]-3-pyridyl]oxy] benzonitrile, 4-[[6-[2-(2,4-difluorophenyl)-1 , 1 -difluoro-2- hydroxy-3-(5-sulfanyl-1 ,2,4-triazol-1 -yl)propyl]-3-pyridyl]oxy] benzonitrile, 4-[[6-[2- (2,4-difluorophenyl)-1 , 1 -difluoro-2-hydroxy-3-(5-thioxo-4H-1 ,2 , 4-triazol-1 -y l)propy l]-3- pyridyl]oxy]benzonitrile, trinexapac, coumoxystrobin, zhongshengmycin, thiodiazole copper, zinc thiazole, amectotractin, iprodione, N-octyl-N'-[2- (octylamino)ethyl]ethane-1 ,2-diamine; N'-[5-bromo-2-methyl-6-[(1 S)-1 -methyl-2- propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1 R)-1 -methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formam idine, N'-[5-bromo-

2-methyl-6-(1 -methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formam idine, N'- [5-chloro-2-methyl-6-(1 -methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl- formamidine, N'-[5-bromo-2-methyl-6-(1 -methyl-2-propoxy-ethoxy)-3-pyridyl]-N- isopropyl-N-methyl-formamidine (these compounds may be prepared from the methods described in WO2015/155075); N'-[5-bromo-2-methyl-6-(2- propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (this compound may be prepared from the methods described in IPCOM000249876D); N-isopropyl-N’-[5- methoxy-2-methyl-4-( 2 ,2 , 2-trif luoro-1 -hydroxy-1 -phenyl-ethyl)phenyl]-N-methyl- formamidine, N’-[4-(1 -cyclopropyl-2,2,2-trifluoro-1 -hydroxy-ethyl)-5-methoxy-2- methyl-phenyl]-N-isopropyl-N-methyl-formamidine (these compounds may be prepared from the methods described in WO2018/228896); N-ethyl-N’-[5-methoxy-2- methyl-4-[(2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-fo rmamidine, N-ethyl-N’-[5- methoxy-2-methyl-4-[(2-trifuoromethyl)tetrahydrofuran-2-yl]p henyl]-N-methyl- formamidine (these compounds may be prepared from the methods described in WO201 9/110427); N-[(1 R)-1-benzyl-3-chloro-1 -methyl-but-3-enyl]-8-fluoro-quinoline-

3-carboxamide, N-[(1 S)-1 -benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3- carboxamide, N-[(1 R)-1 -benzyl-3,3,3-trifluoro-1 -methyl-propyl]-8-fluoro-quinoline-3- carboxamide, N-[(1 S)-1 -benzyl-3,3,3-trifluoro-1 -methyl-propyl]-8-fluoro-quinoline-3- carboxamide, N-[(1 R)-1 -benzyl-1 ,3-dimethyl-butyl]-7,8-difluoro-quinoline-3- carboxamide, N-[(1 S)-1 -benzyl-1 ,3-dimethyl-butyl]-7,8-difluoro-quinoline-3- carboxamide, 8-fluoro-N-[(1 R)-1-[(3-fluorophenyl)methyl]-1 ,3-dimethyl- butyl]quinoline-3-carboxamide, 8-fluoro-N-[(1 S)-1 -[(3-fluorophenyl)methyl]-1 ,3- dimethyl-butyl]quinoline-3-carboxamide, N-[(1 R)-1 -benzyl-1 ,3-dimethyl-butyl]-8- fluoro-quinoline-3-carboxamide, N-[(1 S)-1 -benzyl-1 ,3-dimethyl-butyl]-8-fluoro- quinoline-3-carboxamide, N-((1 R)-1 -benzyl-3-chloro-1 -methyl-but-3-enyl)-8-fluoro- quinoline-3-carboxamide, N-((1 S)-1 -benzyl-3-chloro-1 -methyl-but-3-enyl)-8-fluoro- quinoline-3-carboxamide (these compounds may be prepared from the methods described in WO2017/153380); 1-(6,7-dimethylpyrazolo[1 ,5-a]pyridin-3-yl)-4, 4, 5- trifluoro-3, 3-dimethyl-isoquinoline, 1-(6,7-dimethylpyrazolo[1 ,5-a]pyridin-3-yl)-4,4,6- trifluoro-3,3-dimethyl-isoquinoline, 4,4-difluoro-3,3-dimethyl-1 -(6-methylpyrazolo[1 ,5- a]pyridin-3-yl)isoquinoline, 4,4-difluoro-3,3-dimethyl-1 -(7-methylpyrazolo[1 ,5- a]pyridin-3-yl)isoquinoline, 1 -(6-chloro-7-methyl-pyrazolo[1 , 5-a]pyrid in-3-y l)-4,4- difluoro-3, 3-dimethyl-isoquinoline (these compounds may be prepared from the methods described in WO2017/025510); 1 -(4, 5-dimethylbenzimidazol-1-yl)-4, 4, 5- trifluoro-3, 3-dimethyl-isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3, 3-dimethyl-isoquinoline, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol- 1 -yl)isoquinoline, 4,4-difluoro-1 -(5-fluoro-4-methyl-benzimidazol-1 -yl)-3, 3-dimethyl- isoquinoline, 3-(4,4-difluoro-3,3-dimethyl-1 -isoquinolyl)-7,8-dihydro-6H- cyclopenta[e]benzimidazole (these compounds may be prepared from the methods described in WO2016/156085); N-methoxy-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol- 3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5- (trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl- N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 1- methoxy-3-methyl-1 -[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1 ,3-dimethoxy-1 -[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 3- ethyl-1 -methoxy-1 -[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea, N- [[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-

2-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 5,5- dimethyl-2-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3- one, ethyl 1 -[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4- carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]-1 ,2,4-triazol-3-amine. The compounds in this paragraph may be prepared from the methods described in WO 2017/055473, WO 2017/055469, WO 2017/093348 and WO 2017/118689; 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3- pyridyl]-1 -(1 ,2,4-triazol-1 -yl)propan-2-ol (this compound may be prepared from the methods described in WO 2017/029179); 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-

3-pyridyl]-1 -(1 ,2,4-triazol-1 -yl)propan-2-ol (this compound may be prepared from the methods described in WO 2017/029179); 3-[2-(1-chlorocyclopropyl)-3-(2- fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound may be prepared from the methods described in WO 2016/156290); 3-[2-(1 - chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-pr opyl]imidazole-4- carbonitrile (this compound may be prepared from the methods described in WO 2016/156290); (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate (this compound may be prepared from the methods described in WO 2014/006945); 2,6-Dimethyl-1 H,5H-[1 ,4]dithiino[2, 3-c: 5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetrone (this compound may be prepared from the methods described in WO 2011/138281 ); N- methyl-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzenecarbothioamide; N-methyl- 4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide; (Z,2E)-5-[1 -(2,4- dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl- pent-3-enamide (this compound may be prepared from the methods described in WO 2018/153707); N'-(2- chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidi ne; N'-[2-chloro-4-(2- fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine (this compound may be prepared from the methods described in WO 2016/202742); 2-(difluoromethyl)-N- [(3S)-3-ethyl-1 ,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (this compound may be prepared from the methods described in WO 2014/095675); (5-methyl-2-pyridyl)-[4- [5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methanone, (3-methylisoxazol-5-yl)- [4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methanone (these compounds may be prepared from the methods described in WO 2017/220485); 2-oxo-N-propyl-2-[4- [5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]acetamide (this compound may be prepared from the methods described in WO 2018/065414); ethyl 1-[[5-[5- (trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate (this compound may be prepared from the methods described in WO 2018/158365) ; 2,2- difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]acetamide, N- [(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide, N- [(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide, N-[N- methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]benzamide (these compounds may be prepared from the methods described in WO 2018/202428); microbials including: Acinetobacter Iwoffii, Acremonium alternatum, Acremonium cephalosporium, Acremonium diospyri, Acremonium obclavatum, Adoxophyes orana granulovirus (AdoxGV) (Capex®), Agrobacterium radiobacter strain K84 (Galltrol- A®), Alternaria alternate, Alternaria cassia, Alternaria destruens (Smolder®), Ampelomyces quisqualis (AQ10®), Aspergillus flavus AF36 (AF36®), Aspergillus flavus NRRL 21882 (Aflaguard®), Aspergillus spp., Aureobasidium pullulans, Azospirillum, (MicroAZ®, TAZO B®), Azotobacter, Azotobacter chroocuccum (Azotomeal®), Azotobacter cysts (Bionatural Blooming Blossoms®), Bacillus amyloliquefaciens, Bacillus cereus, Bacillus chitinosporus strain CM-1 , Bacillus chitinosporus strain AQ746, Bacillus licheniformis strain HB-2 (Biostart™ Rhizoboost®), Bacillus licheniformis strain 3086 (EcoGuard®, Green Releaf®), Bacillus circulans, Bacillus firmus (BioSafe®, BioNem-WP®, VOTiVO®), Bacillus firmus strain 1-1582, Bacillus macerans, Bacillus marismortui, Bacillus megaterium, Bacillus mycoides strain AQ726, Bacillus papillae (Milky Spore Powder®), Bacillus pumilus spp., Bacillus pumilus strain GB34 (Yield Shield®), Bacillus pumilus strain AQ717, Bacillus pumilus strain QST 2808 (Sonata®, Ballad Plus®), Bacillus spahericus (VectoLex®), Bacillus spp., Bacillus spp. strain AQ175, Bacillus spp. strain AQ177, Bacillus spp. strain AQ178, Bacillus subtilis strain QST 713 (CEASE®, Serenade®, Rhapsody®), Bacillus subtilis strain QST 714 (JAZZ®), Bacillus subtilis strain AQ153, Bacillus subtilis strain AQ743, Bacillus subtilis strain QST3002, Bacillus subtilis strain QST3004, Bacillus subtilis var. amyloliquefaciens strain FZB24 (Taegro®, Rhizopro®), Bacillus thuringiensis Cry 2Ae, Bacillus thuringiensis CrylAb, Bacillus thuringiensis aizawai GC 91 (Agree®), Bacillus thuringiensis israelensis (BMP123®, Aquabac®, VectoBac®), Bacillus thuringiensis kurstaki (Javelin®, Deliver®, CryMax®, Bonide®, Scutella WP®, Turilav WP ®, Astuto®, Dipel WP®, Biobit®, Foray®), Bacillus thuringiensis kurstaki BMP 123 (Baritone®), Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF 13P®), Bacillus thuringiensis strain BD#32, Bacillus thuringiensis strain AQ52, Bacillus thuringiensis var. aizawai (XenTari®, DiPei®), bacteria spp. (GROWMEND®, GROWSWEET®, Shootup®), bacteriophage of Clavipacter michiganensis (AgriPhage®), Bakflor®, Beauveria bassiana (Beaugenic®, Brocaril WP®), Beauveria bassiana GHA (Mycotrol ES®, Mycotrol O®, BotaniGuard®), Beauveria brongniartii (Engerlingspilz®, Schweizer Beauveria®, Melocont®), Beauveria spp., Botrytis cineria, Bradyrhizobium japonicum (TerraMax®), Brevibacillus brevis, Bacillus thuringiensis tenebrionis (Novodor®), BtBooster, Burkholderia cepacia (Deny®, Intercept®, Blue Circle®), Burkholderia gladii, Burkholderia gladioli, Burkholderia spp., Canadian thistle fungus (CBH Canadian Bioherbicide®), Candida butyri, Candida famata, Candida fructus, Candida glabrata, Candida guilliermondii, Candida melibiosica, Candida oleophila strain O, Candida parapsilosis, Candida pelliculosa, Candida pulcherrima, Candida reukaufii, Candida saitoana (Bio-Coat®, Biocure®), Candida sake, Candida spp., Candida tenius, Cedecea dravisae, Cellulomonas flavigena, Chaetomium cochliodes (Nova- Cide®), Chaetomium globosum (Nova-Cide®), Chromobacterium subtsugae strain PRAA4-1T (Grandevo®), Cladosporium cladosporioides, Cladosporium oxysporum, Cladosporium chlorocephalum, Cladosporium spp., Cladosporium tenuissimum, Clonostachys rosea (EndoFine®), Colletotrichum acutatum, Coniothyrium minitans (Cotans WG®), Coniothyrium spp., Cryptococcus albidus (YIELDPLUS®), Cryptococcus humicola, Cryptococcus infirmo-miniatus, Cryptococcus laurentii, Cryptophlebia leucotreta granulovirus (Cryptex®), Cupriavidus campinensis, Cydia pomonella granulovirus (CYD-X®), Cydia pomonella granulovirus (Madex®, Madex Plus®, Madex Max/ Carpovirusine®), Cylindrobasidium laeve (Stumpout®), Cylindrocladium, Debaryomyces hansenii, Drechslera hawaiinensis, Enterobacter cloacae, Enterobacteriaceae, Entomophtora virulenta (Vektor®), Epicoccum nigrum, Epicoccum purpurascens, Epicoccum spp., Filobasidium floriforme, Fusarium acuminatum, Fusarium chlamydosporum, Fusarium oxysporum (Fusaclean® / Biofox C®), Fusarium proliferatum, Fusarium spp., Galactomyces geotrichum, Gliocladium catenulatum (Primastop®, Prestop®), Gliocladium roseum, Gliocladium spp. (SoilGard®), Gliocladium virens (Soilgard®), Granulovirus (Granupom®), Halobacillus halophilus, Halobacillus litoralis, Halobacillus trueperi, Halomonas spp., Halomonas subglaciescola, Halovibrio variabilis, Hanseniaspora uvarum, Helicoverpa armigera nucleopolyhedrovirus (Helicovex®), Helicoverpa zea nuclear polyhedrosis virus (Gemstar®), Isoflavone - formononetin (Myconate®), Kloeckera apiculata, Kloeckera spp., Lagenidium giganteum (Laginex®), Lecanicillium longisporum (Vertiblast®), Lecanicillium muscarium (Vertikil®), Lymantria Dispar nucleopolyhedrosis virus (Disparvirus®), Marinococcus halophilus, Meira geulakonigii, Metarhizium anisopliae (Met52®), Metarhizium anisopliae (Destruxin WP®), Metschnikowia fruticola (Shemer®), Metschnikowia pulcherrima, Microdochium dimerum (Antibot®), Micromonospora coerulea, Microsphaeropsis ochracea, Muscodor albus 620 (Muscudor®), Muscodor roseus strain A3-5, Mycorrhizae spp. (AMykor®, Root Maximizer®), Myrothecium verrucaria strain AARC-0255 (DiTera®), BROS PLUS®, Ophiostoma piliferum strain D97 (Sylvanex®), Paecilomyces farinosus, Paecilomyces fumosoroseus (PFR-97®, PreFeRal®), Paecilomyces linacinus (Biostat WP®), Paecilomyces lilacinus strain 251 (MeloCon WG®), Paenibacillus polymyxa, Pantoea agglomerans (BlightBan C9- 1®), Pantoea spp., Pasteuria spp. (Econem®), Pasteuria nishizawae, Penicillium aurantiogriseum, Penicillium billai (Jumpstart®, TagTeam®), Penicillium brevicom pactum, Penicillium frequentans, Penicillium griseofulvum, Penicillium purpurogenum, Penicillium spp., Penicillium viridicatum, Phlebiopsis gigantean (Rotstop®), phosphate solubilizing bacteria (Phosphomeal®), Phytophthora cryptogea, Phytophthora palmivora (Devine®), Pichia anomala, Pichia guilermondii, Pichia membranaefaciens, Pichia onychis, Pichia stipites, Pseudomonas aeruginosa, Pseudomonas aureofasciens (Spot-Less Biofungicide®), Pseudomonas cepacia, Pseudomonas chlororaphis (AtEze®), Pseudomonas corrugate, Pseudomonas fluorescens strain A506 (BlightBan A506®), Pseudomonas putida, Pseudomonas reactans, Pseudomonas spp., Pseudomonas syringae (Bio-Save®), Pseudomonas viridiflava, Pseudomons fluorescens (Zequanox®), Pseudozyma flocculosa strain PF- A ₂ 2 UL (Sporodex L®), Puccinia canaliculata, Puccinia thlaspeos (Wood Warrior®), Pythium paroecandrum, Pythium oligandrum (Polygandron®, Polyversum®), Pythium periplocum, Rhanella aquatilis, Rhanella spp., Rhizobia (Dormal®, Vault®), Rhizoctonia, Rhodococcus globerulus strain AQ719, Rhodosporidium diobovatum, Rhodosporidium toruloides, Rhodotorula spp., Rhodotorula glutinis, Rhodotorula gram inis, Rhodotorula mucilagnosa, Rhodotorula rubra, Saccharomyces cerevisiae, Salinococcus roseus, Sclerotinia minor, Sclerotinia minor (SARRITOR®), Scytalidium spp., Scytalidium uredinicola, Spodoptera exigua nuclear polyhedrosis virus (Spod- X®, Spexit®), Serratia marcescens, Serratia plymuthica, Serratia spp., Sordaria fimicola, Spodoptera littoralis nucleopolyhedrovirus (Littovir®), Sporobolomyces roseus, Stenotrophomonas maltophilia, Streptomyces ahygroscopicus, Streptomyces albaduncus, Streptomyces exfoliates, Streptomyces galbus, Streptomyces griseoplanus, Streptomyces griseoviridis (Mycostop®), Streptomyces lydicus (Actinovate®), Streptomyces lydicus WYEC-108 (ActinoGrow®), Streptomyces violaceus, Tilletiopsis minor, Tilletiopsis spp., Trichoderma asperellum (T34 Biocontrol®), Trichoderma gamsii (Tenet®), Trichoderma atroviride (Plantmate®), Trichoderma hamatum TH 382, Trichoderma harzianum rifai (Mycostar®), Trichoderma harzianum T-22 (Trianum-P®, Plantshield HC®, RootShield®, Trianum- G®), Trichoderma harzianum T-39 (Trichodex®), Trichoderma inhamatum, Trichoderma koningii, Trichoderma spp. LC 52 (Sentinel®), Trichoderma lignorum, Trichoderma longibrachiatum, Trichoderma polysporum (Binab T®), Trichoderma taxi, Trichoderma virens, Trichoderma virens (formerly Gliocladium virens GL-21 ) (SoilGuard®), Trichoderma viride, Trichoderma viride strain ICC 080 (Remedier®), Trichosporon pullulans, Trichosporon spp., Trichothecium spp., Trichothecium roseum, Typhula phacorrhiza strain 94670, Typhula phacorrhiza strain 94671 , Ulocladium atrum, Ulocladium oudemansii (Botry-Zen®), Ustilago maydis, various bacteria and supplementary micronutrients (Natural II®), various fungi (Millennium Microbes®), Verticillium chlamydosporium, Verticillium lecanii (Mycotal®, Vertalec®), Vip3Aa20 (VIPtera®), Virgibaclillus marismortui, Xanthomonas campestris pv. Poae (Camperico®), Xenorhabdus bovienii, Xenorhabdus nematophilus;

Plant extracts including: pine oil (Retenol®), azadirachtin (Plasma Neem Oil®, AzaGuard®, MeemAzal®, Molt-X®, Botanical IGR (Neemazad®, Neemix®), canola oil (Lilly Miller Vegol®), Chenopodium ambrosioides near ambrosioides (Requiem®), Chrysanthemum extract (Crisant®), extract of neem oil (Trilogy®), essentials oils of Labiatae (Botania®), extracts of clove rosemary peppermint and thyme oil (Garden insect killer®), Glycinebetaine (Greenstim®), garlic, lemongrass oil (GreenMatch®), neem oil, Nepeta cataria (Catnip oil), Nepeta catarina, nicotine, oregano oil (MossBuster®), Pedaliaceae oil (Nematon®), pyrethrum, Quillaja saponaria (NemaQ®), Reynoutria sachalinensis (Regalia®, Sakalia®), rotenone (Eco Roten®), Rutaceae plant extract (Soleo®), soybean oil (Ortho ecosense®), tea tree oil (Timorex Gold®), thymus oil, AGNIQUE® MMF, BugOil®, mixture of rosemary sesame pepermint thyme and cinnamon extracts (EF 300®), mixture of clove rosemary and peppermint extract (EF 400®), mixture of clove pepermint garlic oil and mint (Soil Shot®), kaolin (Screen®), storage glucam of brown algae (Laminarin®); pheromones including: blackheaded fireworm pheromone (3M Sprayable Blackheaded Fireworm Pheromone®), Codling Moth Pheromone (Paramount dispenser-(CM)/ Isomate C-Plus®), Grape Berry Moth Pheromone (3M MEC-GBM Sprayable Pheromone®), Leafroller pheromone (3M MEC - LR Sprayable Pheromone®), Muscamone (Snip7 Fly Bait®, Starbar Premium Fly Bait®), Oriental Fruit Moth Pheromone (3M oriental fruit moth sprayable pheromone®), Peachtree Borer Pheromone (Isomate-P®), Tomato Pinworm Pheromone (3M Sprayable pheromone®), Entostat powder (extract from palm tree) (Exosex CM®), (E,Z,Z)- 3,8,11 Tetradecatrienyl acetate, (Z,Z,E)-7,11 ,13-Hexadecatrienal, (E,Z)-7,9- Dodecadien-1-yl acetate, 2-Methyl-1 -butanol, Calcium acetate, Scenturion®, Biolure®, Check-Mate®, Lavandulyl senecioate; Macrobials including: Aphelinus abdominalis, Aphidius ervi (Aphelinus-System®), Acerophagus papaya, Adalia bipunctata (Adalia-System®), Adalia bipunctata (Adaline®), Adalia bipunctata (Aphidalia®), Ageniaspis citricola, Ageniaspis fuscicollis, Amblyseius andersoni (Anderline®, Andersoni-System®), Amblyseius californicus (Amblyline®, Spical®), Amblyseius cucumeris (Thripex®, Bugline cucumeris®), Amblyseius fallacis (Fallacis®), Amblyseius swirskii (Bugline swirskii®, Swirskii-Mite®), Amblyseius womersleyi (WomerMite®), Amitus hesperidum, Anagrus atomus,

Anagyrus fusciventris, Anagyrus kamali, Anagyrus loecki, Anagyrus pseudococci (Citripar®), Anicetus benefices, Anisopteromalus calandrae, Anthocoris nemoralis (Anthocoris-System®), Aphelinus abdominalis (Apheline®, Aphiline®), Aphelinus asychis, Aphidius colemani (Aphipar®), Aphidius ervi (Ervipar®), Aphidius gifuensis, Aphidius matricariae (Aphipar-M®), Aphidoletes aphidimyza (Aphidend®), Aphidoletes aphidimyza (Aphidoline®), Aphytis lingnanensis, Aphytis melinus, Aprostocetus hagenowii, Atheta coriaria (Staphyline®), Bombus spp., Bombus terrestris (Natupol Beehive®), Bombus terrestris (Beeline®, Tripol®), Cephalonomia stephanoderis, Chilocorus nigritus, Chrysoperla carnea (Chrysoline®), Chrysoperla carnea (Chrysopa®), Chrysoperla rufilabris, Cirrospilus ingenuus, Cirrospilus quadristriatus, Citrostichus phyllocnistoides, Closterocerus Chamaeleon, Closterocerus spp., Coccidoxenoides perminutus (Pianopar®), Coccophagus cowperi, Coccophagus lycimnia, Cotesia flavipes, Cotesia plutellae, Cryptolaemus montrouzieri (Cryptobug®, Cryptoline®), Cybocephalus nipponicus, Dacnusa sibirica, Dacnusa sibirica (Minusa®), Diglyphus isaea (Diminex®), Delphastus catalinae (Delphastus®), Delphastus pusillus, Diachasmimorpha krausii, Diachasmimorpha longicaudata, Diaparsis jucunda, Diaphorencyrtus aligarhensis, Diglyphus isaea, Diglyphus isaea (Miglyphus®, Digline®), Dacnusa sibirica (DacDigline®, Minex®), Diversinervus spp., Encarsia citrina, Encarsia formosa (Encarsia max®, Encarline®, En-Strip®), Eretmocerus eremicus (Enermix®), Encarsia guadeloupae, Encarsia haitiensis, Episyrphus balteatus (Syrphidend®), Eretmoceris siphonini, Eretmocerus californicus, Eretmocerus eremicus (Ercal®, Eretline e®), Eretmocerus eremicus (Bemimix®), Eretmocerus hayati, Eretmocerus mundus (Bemipar®, Eretline m®), Eretmocerus siphonini, Exochomus quadripustulatus, Feltiella acarisuga (Spidend®), Feltiella acarisuga (Feltiline®), Fopius arisanus, Fopius ceratitivorus, Formononetin (Wirless Beehome®), Franklinothrips vespiformis (Vespop®), Galendromus occidentalis, Goniozus legneri, Habrobracon hebetor, Harmonia axyridis (HarmoBeetle®), Heterorhabditis spp. (Lawn Patrol®), Heterorhabditis bacteriophora (NemaShield HB®, Nemaseek®, Terranem-Nam®, Terranem®, Larvanem®, B- Green®, NemAttack ®, Nematop®), Heterorhabditis megidis (Nemasys H®, BioNem H®, Exhibitline hm®, Larvanem-M®), Hippodamia convergens, Hypoaspis aculeifer (Aculeifer-System®, Entomite-A®), Hypoaspis miles (Hypoline m®, Entomite-M®), Lbalia leucospoides, Lecanoideus floccissimus, Lemophagus errabundus, Leptomastidea abnormis, Leptomastix dactylopii (Leptopar®), Leptomastix epona, Lindorus lophanthae, Lipolexis oregmae, Lucilia caesar (Natufly®), Lysiphlebus testaceipes, Macrolophus caliginosus (Mirical-N®, Macroline c®, Mirical®), Mesoseiulus longipes, Metaphycus flavus, Metaphycus lounsburyi, Micromus angulatus (Milacewing®), Microterys flavus, Muscidifurax raptorellus and Spalangia cameroni (Biopar®), Neodryinus typhlocybae, Neoseiulus californicus, Neoseiulus cucumeris (THRYPEX®), Neoseiulus fallacis, Nesideocoris tenuis

(NesidioBug®, Nesibug®), Ophyra aenescens (Biofly®), Orius insidiosus (Thripor-I®, Online i®), Orius laevigatus (Thripor-L®, Oriline I®), Orius majusculus (Online m®), Orius strigicollis (Thripor-S®), Pauesia juniperorum, Pediobius foveolatus, Phasmarhabditis hermaphrodita (Nemaslug®), Phymastichus coffea, Phytoseiulus macropilus, Phytoseiulus persim ilis (Spidex®, Phytoline p®), Podisus maculiventris (Podisus®), Pseudacteon curvatus, Pseudacteon obtusus, Pseudacteon tricuspis, Pseudaphycus maculipennis, Pseudleptomastix mexicana, Psyllaephagus pilosus, Psyttalia concolor (complex), Quadrastichus spp., Rhyzobius lophanthae, Rodolia cardinalis, Rumina decollate, Semielacher petiolatus, Sitobion avenae (Ervibank®), Steinernema carpocapsae (Nematac C®, Millenium®, BioNem C®, NemAttack®, Nemastar®, Capsanem®), Steinernema feltiae (NemaShield®, Nemasys F®, BioNem F®, Steinernema-System®, NemAttack®, Nemaplus®, Exhibitline st®, Scia- rid®, Entonem®), Steinernema kraussei (Nemasys L®, BioNem L®, Exhibitline srb®), Steinernema riobrave (BioVector®, BioVektor®), Steinernema scapterisci (Nematac S®), Steinernema spp., Steinernematid spp. (Guardian Nematodes®), Stethorus punctillum (Stethorus®), Tamarixia radiate, Tetrastichus setifer, Thripobius semiluteus, Torymus sinensis, Trichogramma brassicae (Tricholine b®), Trichogramma brassicae (Tricho-Strip®), Trichogramma evanescens, Trichogramma minutum, Trichogramma ostriniae, Trichogramma platneri, Trichogramma pretiosum, Xanthopimpla stemmator; other biologicals including: abscisic acid, bioSea®, Chondrostereum purpureum (Chontrol Paste®), Colletotrichum gloeosporioides (Collego®), Copper Octanoate (Cueva®), Delta traps (Trapline d®), Erwinia amylovora (Harpin) (ProAct®, Ni-HIBIT Gold CST®), Ferri-phosphate (Ferramol®), Funnel traps (Trapline y®), Gallex®, Grower's Secret®, Homo-brassonolide, Iron Phosphate (Lilly Miller Worry Free Ferramol Slug & Snail Bait®), MCP hail trap (Trapline f®), Microctonus hyperodae, Mycoleptodiscus terrestris (Des-X®), BioGain®, Aminomite®, Zenox®, Pheromone trap (Thripline ams®), potassium bicarbonate (MilStop®), potassium salts of fatty acids (Sanova®), potassium silicate solution (Sil-Matrix®), potassium iodide + potassiumthiocyanate (Enzicur®), SuffOil-X®, Spider venom, Nosema locustae (Semaspore Organic Grasshopper Control®), Sticky traps (Trapline YF®, Rebell Amarillo®) and Traps (Takitrapline y + b®); and a safener, such as benoxacor, cloquintocet (including cloquintocet-mexyl), cyprosulfamide, dichlormid, fenchlorazole (including tench lorazole-ethyl), fenclorim, fluxofenim, furilazole, isoxadifen (including isoxadifen-ethyl), mefenpyr (including mefenpyr-diethyl), metcamifen and oxabetrinil.

Where the active ingredients are included in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; 13 ^th Ed.; Editor: C. D. S. TomLin; The British Crop Protection Council], they are described therein under the entry number given in round brackets hereinabove for the particular compound; for example, the compound "abamectin" is described under entry number (1). Where "[CCN]" is added hereinabove to the particular compound, the compound in question is included in the "Compendium of Pesticide Common Names", which is accessible on the internet [A. Wood; Compendium of Pesticide Common Names, Copyright © 1995-2004]; for example, the compound "acetoprole" is described under the internet address http://www.alanwood.net/pesticides/acetoprole.html.

Most of the active ingredients described above are referred to hereinabove by their "common name" which is known to the skilled person in the art. In other cases, the active ingredients may be referred to by their IIIPAC name The term “CAS number” means the Chemical Abstracts Registry Number.

Preferably, the one or more other active ingredients that may optionally present in the compositions of the invention are selected from Alpha-Cypermethrin, Bifenthrin, Broflanilide, Chlorantraniliprole, Clothianidin, Cyantraniliprole, Cypermethrin, Deltamethrin, Dicloromezotiaz, dimpropyridaz, Emamectin (or Emamectin Benzoate), Fluazaindolizine, Flubendiamide, Fluopyram, Imidacloprid, Indoxacarb, Isocycloseram, Lambda-Cyhalothrin, Permethrin, Spinetoram, Spinosad, Spiropidion, Spirotetramat, Sulfoxaflor, Tetraniliprole, Thiamethoxam, Tioxazafen, Bacillus thuringiensis, Helicoverpa armigera Nucleopolyhedrovirus and beta-cyfluthrin.

The active ingredient mixture of the compounds of formula I with active ingredients described above comprises preferably in a mixing ratio by weight of from 100:1 to 1 :6000, especially from 50:1 to 1 :50, more especially in a ratio of from 20:1 to 1 :20, even more especially from 10:1 to 1 :10, very especially from 5:1 and 1 :5, special preference being given to a ratio of from 2:1 to 1 :2, and a ratio of from 4:1 to 2:1 being likewise preferred, above all in a ratio of 1 :1 , or 5:1 , or 5:2, or 5:3, or 5:4, or 4:1 , or 4:2, or 4:3, or 3:1 , or 3:2, or 2:1 , or 1 :5, or 2:5, or 3:5, or 4:5, or 1 :4, or 2:4, or 3:4, or 1 :3, or 2:3, or 1 :2, or 1 :600, or 1 :300, or 1 :150, or 1 :35, or 2:35, or 4:35, or 1 :75, or 2:75, or 4:75, or 1 :6000, or 1 :3000, or 1 : 1500, or 1 :350, or 2:350, or 4:350, or 1 :750, or 2:750, or 4:750.

Use of the compounds and compositions in insect and/or pests of the order Acarina

The compounds according to the first aspect of the invention and the compositions according to the second aspect of the invention as described above may be used in agriculture, in particular in controlling insect pests and/or pests of the order Acarina damaging crops. Therefore, the present invention provides in a third aspect of the present invention the use of the compound according to the first aspect of the invention or the composition according to the second aspect of the invention in agriculture.

In addition, as a fourth aspect of the present invention, it is provided a method for controlling insect pests and/or pests of the order Acarina damaging crops, wherein the method comprises applying to a pest, to a locus of a pest, to a plant susceptible to attack by a pest or to a plant propagation material an effective amount of the compound according to the first aspect of the present invention or a composition according to the second aspect of the present invention.

The compounds according to the first aspect of the invention and/or the compositions according to the second aspect of the invention are especially suitable for efficiently combating animal pests e.g. arthropods, and nematodes including: insects from the sub-order of Auchenorrhyncha, e.g. Amrasca biguttula, Empoasca spp., Ne- photettix virescens, Sogatella furcifera, Mahanarva spp., Laodelphax striatellus, Nilaparvata lugens, Diaphorina citrr, Lepidoptera, e.g. Helicoverpa spp., Heliothis virescens, Lobesia botrana, Ostrinia nubilalis, Plutella xylostella, Pseudoplusia includens, Scirpophaga incertulas, Spodoptera spp., Trichoplu- sia ni, Tuta absoluta, Cnaphalocrocis medians, Cydia pomonella, Chilo suppressalis, Anticarsia gemmatalis, Agrotis ipsilon, Chrysodeixis includens-, True bugs, e.g. Lygus spp., Stink bugs such as Euschistus spp., Halyomorpha halys, Nezara viridula, Piezodorus guildinii, Dichelops furcatus ; Thrips, e.g. Frankliniella spp., Thrips spp., Dichromothrips corbettir, Aphids, e.g. Acyrthosiphon pisum, Aphis spp., Myzus persicae, Rhopalosiphum spp., Schi- zaphis graminum, Megoura viciae\ Whiteflies, e.g. Thaleurodes vaporariorum, Bemisia spp.; Coleoptera, e.g. Phyllotreta spp., Melanotus spp., Meligethes aeneus, Leptinotarsa decimline- ata, Ceutorhynchus spp., Diabrotica spp., Anthonomus grandis, Atomaha linearia, Agriotes spp., Epilachna spp.; Flies, e.g. Delia spp., Ceratitis capitate, Bactrocera spp., Liriomyza spp.; Coccoidea, e.g. Aonidiella aurantia, Ferrisia virgate; Anthropods of class Arachnida (Mites), e.g. Penthaleus major, Tetranychus spp.; Nematodes, e.g. Heterodera glycines, Meloidogyne spp., Pratylenchus spp., Caenorhabditis elegans.

The compounds and/or compositions of the invention may also be suitable for use in treating or protecting animals against infestation or infection by parasites, such as animals on pets like fleas.

In addition, the compounds according to the first aspect of the invention and/or the compositions according to the second aspect of the invention are especially suitable for efficiently combating pests from the order Acarina, for example, Acalitus spp, Aculus spp, Acaricalus spp, Aceria spp, Acarus siro, Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia spp, Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides spp, Eotetranychus spp, Eriophyes spp., Hemitarsonemus spp.

In the method according to the fourth aspect, a composition according to the second aspect of the invention as described above can be applied, for example, in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a “tank-mix”, and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days. The order of applying the compounds according to the first aspect of the present invention and further other active ingredients as described above, if present, is not essential.

The application methods for the compounds and compositions, that is the methods of controlling the indicated pests, such as spraying, atomizing, dusting, brushing on, dressing, scattering or pouring - which are to be selected to suit the intended aims of the prevailing circumstances - and the use of the compounds and compositions for controlling pests of the abovementioned type are subjects of the invention. Typical rates of concentration are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm, of active ingredient. The rate of application per hectare is generally 1 to 2000 g of active ingredient per hectare, in particular 10 to 1000 g/ha, preferably 10 to 600 g/ha.

A preferred method of application in the field of crop protection is application to the foliage of the plants (foliar application), it being possible to select frequency and rate of application to match the danger of infestation with the pest in question.

Alternatively, the active ingredient can reach the plants via the root system (systemic action), by drenching the locus of the plants with a liquid composition or by incorporating the active ingredient in solid form into the locus of the plants, for example into the soil, for example in the form of granules (soil application). In the case of paddy rice crops, such granules can be metered into the flooded paddy-field.

The compounds according to the first aspect of the invention and compositions thereof according to the second aspect of the invention are to be also suitable for the protection of crops, plants, plant propagation materials, e.g. seeds, or soil or water, in which the plants are growing, from attack or infestation by animal pests. Therefore, the invention also relates to a plant protection method, which comprises contacting crops, plants, plant propagation materials, e.g. seeds, or soil or water, in which the plants are growing, to be protected from attack or infestation by animal pests, with a pesticidally effective amount of a compound according to the first aspect of the invention or a composition according to the second aspect of the invention.

The term “plant” includes cereals, e.g. durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder maize and sugar maize / sweet and field corn); beet, e.g. sugar beet, or fodder beet; fruits, e.g. pomes, stone fruits, or soft fruits, e.g. apples, pears, plums, peaches, nectarines, almonds, cherries, papayas, strawberries, raspberries, blackberries or gooseberries; leguminous plants, e.g. beans, lentils, peas, alfalfa, or soybeans; oil plants, e.g. rapeseed (oilseed rape), turnip rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts, or soybeans; cucurbits, e.g. squashes, pumpkins, cucumber or melons; fiber plants, e.g. cotton, flax, hemp, or jute; citrus fruit, e.g. oranges, lemons, grapefruits or mandarins; vegetables, e.g. eggplant, spinach, lettuce (e.g. iceberg lettuce), chicory, cabbage, asparagus, cabbages, carrots, onions, garlic, leeks, tomatoes, potatoes, cucurbits or sweet pep pers; lauraceous plants, e.g. avocados, cinnamon, or camphor; energy and raw material plants, e.g. corn, soybean, rapeseed, sugar cane or oil palm; tobacco; nuts, e.g. walnuts; pistachios; coffee; tea; bananas; vines; hop; sweet leaf (Stevia); natural rubber plants or ornamental and forestry plants, , shrubs, broad-leaved trees or evergreens, eucalyptus; turf; lawn; grass. Preferred plants include potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, com, cotton, soybeans, rapeseed, legumes, sunflowers, coffee, or sugar cane; fruits; vines; ornamentals; or vegetables, e.g. cucumbers, tomatoes, beans or squashes.

.. It is also possible to apply the compositions when the propagation material is planted to the site of application, for example into the seed furrow during drilling. These treatment methods for plant propagation material and the plant propagation material thus treated are further subjects of the invention. Typical treatment rates would depend on the plant and pest/fungi to be controlled and are generally between 1 to 200 grams per 100 kg of seeds, preferably between 5 to 150 grams per 100 kg of seeds, such as between 10 to 100 grams per 100 kg of seeds.

The term seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, coms, bulbs, fruit, tubers, grains, rhizomes, cuttings, cut shoots and the like and means in a preferred embodiment true seeds.

The present invention also comprises seeds coated or treated with or containing a compound of formula I. The term "coated or treated with and/or containing" generally signifies that the active ingredient is for the most part on the surface of the seed at the time of application, although a greater or lesser part of the ingredient may penetrate into the seed material, depending on the method of application. When the said seed product is (re)planted, it may absorb the active ingredient. In an embodiment, the present invention makes available a plant propagation material adhered thereto with a compound of formula I. Further, it is hereby made available, a composition comprising a plant propagation material treated with a compound of formula I.

Seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting. The seed treatment application of the compound according to the first aspect of the invention or the composition according to the second aspect of the invention can be carried out by any known methods, such as spraying or by dusting the seeds before

EXAMPLES

The present invention will be demonstrated in more detail by way of examples which are not intended to be limiting.

1) General Methods

Flash chromatography was carried out using a Biotage Isolera 4, with Biotage® SNAP KP-Sil cartridges, packed with 50 pm silica particles with a surface area of 500 m ² /g, or alternative cartridges (e.g. Puriflash, produced by Interchim) where stated, or using silica gel (40-63 pm particles). Visualisation was carried out with UV light (254 nm) and by staining with either potassium permanganate, phosphomolybdic acid (PMA) or ninhydrin solutions. All ¹ H NMR spectra were obtained on a Broker AVIII 400 with 5mm QNP or Broker AVI 500 with 5mm QNP. Chemical shifts (5) are expressed in parts per million (ppm) and are referenced to the solvent. Coopling constants J are expressed in Hertz (Hz).

MS was carried on a Waters HCIass UPLC-QDA UV-MS system osing Methods A/C (high pH) or Method B/D (low pH):

Method A (5 min basic pH)

Mobile phases: Water (A) I Acetonitrile (B) I WaterAcetonitrile 50:50 with 1 % (v/v) NH ₄ OH (C)

3 pl injection, Colomn XBridge BEH C ₁ 8 Colomn 3.0 x 50mm @ 35°C.

Method B (5 min acidic pH)

Mobile phases: Water (A) I Acetonitrile (B) I WaterAcetonitrile 50:50 with 1 % (v/v) formic acid (D)

3 pl injection, Colomn: HSelect HSS Colomn 3.0 x 50mm @ 35°C.

Method C (15 min basic pH)

Mobile phases: Water (A) I Acetonitrile (B) I WaterAcetonitrile 50:50 with 1 % (v/v)

NH4OH (C)

3 pl injection, Colomn XBridge BEH C ₁ 8 Colomn 3.0 x 50mm @ 35°C. Method D (15 min acidic pH)

Mobile phases: Water (A) I Acetonitrile (B) I WaterAcetonitrile 50:50 with 1 % (v/v) formic acid (D)

3 pl injection, Column: HSelect HSS Column 3.0 x 50mm @ 35°C.

Method E (15 min, GCMS)

GC-Mass was taken on Agilent 7890B series instrument with MSD 5977B. Column: HP-5MS (30 x 250pm x 0.25pm). Carrier Gas: Helium. Inlet Temperature: 250 °C. Split ratio: 30 :1. Gas flow: 1.0 ml/min. Ramp Profile: Oven temperature initial from 60°C held for 2min then, 100°C increasing at the rate of 20°C held for 2min,.310°C increasing at the rate of 40°C held for 4min. Total run time is 15.25 min.

Method F (5 min, basic pH)

LCMS was carried on a Waters H Class UPLC-SQD 2 PDA-MS system Mobile phases: 5 mM Ammonium Acetate in Water (A) 15 mM Ammonium Acetate in WaterAcetonitrile (10:90) (B)

2 pl injection, Column XBridge C ₁ 8 Column 3 x 50mm, 3.5 u @ 40°C.

Method G (preparative HPLC)

Waters auto purification instrument. Column name: YMC-Actus Triart C ₁ 8 (250 x 20 mm, 5pm) operating at ambient temperature and flow rate of 16 mL/min. Mobile phase: 20 mM NH4HCO3 in water (A) / Acetonitrile (B);

Method H (20 min, basic pH)

LCMS was carried out with an Applied Biosystem's API 2000 mass spec attached with Shimadzu Prominance HPLC system. Mobile phases: 10 mM Ammonium Acetate in Water (A) / Acetonitrile (B)

4 pl injection, Column XBridge C1 8 Column 4.6 x 250mm, 5 u at room temperature

LogD was measured using the shake flask methodology. The aqueous phase used is a 10mM solution of sodium phosphate buffer adjusted to pH 7.4 and Octanol is used as the organic solvent. Quantitation of test compound in both phases is via LC- MS/MS.

All reagents were obtained from commercial suppliers and used as supplied unless otherwise stated.

All compounds are named using ChemBioDraw Ultra 14.0.

The abbreviations used in the following are commonly used in this technical field. For example, the following abbreviations are used: aq - aqueous

DMF - A/,A/-dimethylformamide;

EtOAc - ethyl acetate

DCM - dichloromethane

DIPEA - /V,/V-di isopropylethylamine (also referred to as “Hunig's base”)

MTBE - methyl tert-butyl ether

PE - petroleum ether

PyBOP - benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate rt - room temperature sat - saturated

TEA - triethylamine THF - tetrahydrofuran

2) Preparation of intermediates for the preparation of compounds in accordance with the invention

Intermediate A: Ethyl 1-(pyrimidin-2-yl)-1 /-/-1 ,2,4-triazole-5-carboxylate

To a solution of ethyl 2-amino-2-oxoacetate (200 mg, 1.71 mmol) in DMF (5 mL) was added A/,A/-dimethylformamide dimethyl acetal (0.273 mL, 2.05 mmol). The solution was heated at 70°C for 2 h and then treated with 2-hydrazinopyrimidine (226 mg, 2.05 mmol) and acetic acid (5 mL). The mixture stirred at 90°C for 1 h. The reaction was quenched with sat. NaHCO ₃ (aq) (70 mL) and the mixture was extracted with EtOAc (3x70 mL). The combined organic extracts were dried (MgSO ₄ ) and the solvent was removed under reduced pressure. The residue was chromatographed on silica eluting with PE: EtOAc gradient 3:2 to 0:1 , to give the title compound (120 mg, 32%). LCMS (Method A) 1.19 min, 220.1 (MH ⁺ ).

Intermediate A-1

The following example were prepared using the general method described in Intermediate A from the appropriate intermediates or commercial materials.

Intermediate B: 1 -(pyrimidin-2-yl)-1 H-1 ,2,4-triazole-5-carboxylic acid

To a solution of Intermediate A (380 mg, 1 .73 mmol) in MeOH (2 mL) and water (2 mL) was added sodium hydroxide (139 mg, 3.47 mmol). The reaction mixture was stirred at rt for 1 h and then concentrated in vacuo. The residue was washed with MeOH and the filtrate was concentrated in vacuo to give the title compound (180 mg, 54%).

Intermediate B-1

The following example were prepared using the general method described in Intermediate B from the appropriate intermediates or commercial materials.

Intermediate C: ethyl 2-((1-(3,5-bis(trifluoromethyl)phenyl)ethyl)amino)-2-oxoacet ate

To a solution of 3,5-bis(trifluoromethyl)-alpha-methylbenzylamine (500 mg, 1 .94 mmol) in DCM (10 mL) and triethylamine (0.81 mL, 5.83 mmol) was added dropwise ethyl oxalyl chloride (0.22 mL, 1 .94 mmol). The reaction mixture was stirred at rt for 16 h. Then water (100 mL) was added and the aqueous phase was extracted with DCM (2x100 mL). The organic extracts were dried (MgSO ₄ ) and concentrated in vacuo. The residue was chromatographed on silica eluting with PE:EtOAc gradient 9:1 to 0: 1 , to give the title compound (500 mg, 72%). LCMS (Method A) 2.50 min, 358.0 (MH ⁺ ).

Intermediates C-1 to C-16

The following examples were prepared using the general method described in Intermediate C from the appropriate intermediates or commercial materials.

To a solution of Intermediate C (500 mg, 1 .40 mmol) in EtOH (2.5 mL) was added ammonia in methanol (0.85 mL, 14.0 mmol). The reaction mixture was stirred at rt overnight and then concentration under reduced pressure to give the title compound (410 mg, 89%) as a white solid. LCMS (Method A) 2.20 min, 327.0 (MH-).

Intermediates D-1 to D-16

The following examples were prepared using the general method described in Intermediate D from the appropriate intermediates or commercial materials.

Intermediate E: Methyl 3-(pyridin-2-yl)pyrazine-2-carboxylate To a solution of methyl-3-bromopyrazine-2-carboxylate (200 mg, 0.922 mmol) in DMF (5 mL) was added caesium fluoride (280 mg, 1 .84 mmol), copper (I) iodide (18 mg, 0.092 mmol) and tetrakis(triphenylphosphine)palladium (106 mg, 0.092 mmol).

The mixture was degassed with N2 for 20 mins. 2-(tributylstannyl)pyridine (0.291 ml, 0.922 mmol) was added and the reaction was sealed and stirred under microwave irradiation at 130°C for 30 min. The reaction was diluted with EtOAc and 1 M KF aq. solution was added. The two phases were stirred at room temperature for 1 h and then separated. The organic layer was dried (MgSO ₄ ) and evaporated in vacuo. The residue was chromatographed on silica eluting with PE: EtOAc gradient 90:10 to 30:70, to give the title compound (91 .2 mg, 46%). LCMS (Method A) 1 .42 min, 216.1 (MH ⁺ ).

Intermediates E-1 to E-6 The following examples were prepared using the general method described in Intermediate E from the appropriate intermediates or commercial materials.

Intermediate F: 3-(Pyridin-2-yl)pyrazine-2-carboxylic acid o

A solution of Intermediate E (91 mg, 0.424 mmol) in MeOH (1 mL) and water (1 mL) was treated with sodium hydroxide (40 mg, 1 .00 mmol) and stirred at 80 °C for 30 min. The reaction was allowed to cool to rt and then acidified with 2M HCI (aq.) (pH 4-5). The precipitate formed was filtered out, washed with water to give the title compound (62 mg, 72%). LCMS (Method A) 0.19 min, 202.1 (MH ⁺ ) Intermediates F-1 to F-6

The following examples were prepared using the general method described in Intermediate F from the appropriate intermediates or commercial materials.

Intermediate G: methyl 2-phenylfuran-3-carboxylate

In a microwave vial, methyl 2-bromo-3-furoate (400 mg, 1.95 mmol), phenylboronic acid (357 mg, 2.93 mmol), 1 ,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (36 mg, 0.049 mmol), NaHCO ₃ (516 mg, 6.15 mmol), dioxane (8 ml) and water (2 ml) were added and the solution was purged with nitrogen. The reaction was microwaved at 100 °C for 30 minutes then cooled, filtered and concentrated. The residue was quenched with water, extracted with EtOAc, washed with water and brine. The organic layer was dried (MgSO ₄ ) and concentrated. The residue was chromatographed on silica eluting with PE:EtOAc, gradient 1 :0 to 7:3 to give title compound in moderate yield. LC-MS (Method A) 2.43 min, 203.1 (MH ⁺ ).

Intermediates G-1 to G-3

The following examples were prepared using the general method described in Intermediate G from the appropriate intermediates or commercial materials.

Intermediate H: 2-phenylfuran-3-carboxylic acid

A solution of sodium hydroxide (62 mg, 1 .553 mmol) in water (1 .5 ml) was added to a solution of Intermediate G (157 mg, 0.776 mmol) in THF (3 ml) and the reaction mixture stirred at rt for 1 h. THF was evaporated and the solution adjusted to ~ pH 3 using 1 M HCI. The formed precipitate was filtered and washed with water to give the title compound in good yield. LC-MS (Method B) 2.13 min, 187.1 (MH-).

Intermediates H-1 to H-3 The following examples were prepared using the general method described in Intermediate H from the appropriate intermediates or commercial materials. Intermediate I: ethyl 3-(pyridin-2-yl)isoxazole-4-carboxylate

To a solution of /V-chlorosuccin imide (273 mg, 2.05 mmol) in DMF (5 ml) was added 2-pyridinealdoxime (250 mg, 2.05 mmol) and the resulting mixture was then stirred for 24 h at rt. To this solution was added ethyl 3-(dimethylamino)acrylate (0.293 ml, 2.05 mmol) and triethylamine (0.571 ml, 4.09 mmol) in chloroform (10 mL) and the resulting mixture was then stirred for 14 h at rt and poured onto a mixture of ice water and HCI then extracted with EtOAc. The organic layer washed with water, sat. NaHCO ₃ (aq) solution and brine, dried (MgSO4), filtered and concentrated. The residue was chromatographed on silica eluting with PE: EtOAc gradient 9:1 to 1 :9 to give the title compound in moderate to good yield. LCMS (Method A) 1 .61 min, 219.1 (MH ⁺ ).

Intermediate J: methyl 1-(pyrimidin-2-yl)-1 H-pyrrole-2-carboxylate

Cesium carbonate (1.993 g, 6.12 mmol) and methyl 2-pyrrolecarboxylate (0.421 g, 3.36 mmol) were stirred in DMF (15 ml) for 30 minutes at 70 °C. 2-fluoropyrimidine (0.3 g, 3.06 mmol) was added and the solution was stirred for 16 h. The reaction was diluted with water and extracted with EtOAc. The organic layer was washed with water and brine, dried (MgSO ₄ ) and concentrated The residue was chromatographed on silica eluting with PE: EtOAc gradient 9:1 to 1 :9 to give the title compound in good yield. LCMS (Method A) 1 .48 min, 204.1 (MIT)

I nterm ediate K: methyl 5-phenyloxazole-4-carboxylate

TEA (1 .06 ml, 7.57 mmol) and 4-(dimethylamino)pyridine (0.018 g, 0.151 mmol) were added to a mixture of methyl isocyanoacetate (0.275 ml, 3.03 mmol) and benzoyl chloride (0.422 ml, 3.63 mmol) in THF (4 ml). The reaction mixture was refluxed overnight under nitrogen. After being cooled, the resulting mixture was filtered and the solid was rinsed with EtOAc. The filtrate was diluted with EtOAc, washed with water and brine, dried (MgSO ₄ ), filtered, and concentrated. The residue was chromatographed on silica eluting with PE: EtOAc gradient, 9:1 to 3:2) to give the title compound in moderate to good yield. LCMS (Method A) 1 .87 min, 204.1 (MIT).

Intermediate L: 4-phenylthiazole-5-carboxylic acid

A solution of sodium hydroxide (39 mg, 0.96 mmol) in water (1 ml) was added to a solution of ethyl 4-phenylthiazole-5-carboxylate (150 mg, 0.64 mmol) in MeOH (3 ml) and the reaction mixture stirred at rt for 16 h. The reaction mixture was concentrated and 3M HCI was added. The product was extracted with EtOAc and organic layer were dried (MgSO4) and concentrated to give the title compound good yield. LCMS (Method B) 1.58 min, 206.0 (MH ⁺ ).

Intermediates L1 -L3

The following examples were prepared using the general method described in Intermediate L from the appropriate intermediates or commercial materials.

Intermediate M: 1 -(pyridin-2-yl)-7/-/-pyrazole-5-carboxylic acid

To a solution of 2-(1 H-pyrazol-1 -y I )pyrid ine (250 mg, 1 .72 mmol) in THF (5 ml) was added lithium diisopropylamide 1 M in THF (2.24 ml, 2.24 mmol) dropwise at -78 °C and stirred for 30 min, then carbon dioxide was bubbled to the mixture for 1 h and the reaction allowed to warm to rt. The mixture was added to MTBE and H ₂ O. The water layer was adjusted to pH ~ 4 with 1 M HCI and extracted with EtOAc, the organic lay- er was dried (MgSO ₄ ) and concentrated to give the title compound in low to moderate yield. LCMS (Method B) 1.24 min, 190.0 (MH ⁺ ).

Intermediate N: /V-(3,5-bis(trifluoromethyl)benzyl)-1H-imidazole-2-carboxami de To a stirred solution of 2-imidazolecarboxylic acid (0.5 g, 4.46 mmol) in DMF (20 ml) was added PyBOP (4.64 g, 8.92 mmol) and DIPEA (2.33 ml, 13.38 mmol). 3,5- Bis(trifluoromethyl)benzylamine (1.19 g, 4.91 mmol) was added and the reaction mix- ture was stirred at rt for 72 h. Upon addition of water, an orange precipitate formed. The precipitate was washed with water and EtOAc to give the title compound in low to moderate yield. LCMS (Method A) 2.17 min, 338.0 (MIT).

Intermediate 0: 3-(trifluoromethyl)-5-(4-(trifluoromethyl)-1 H-pyrazol-1 -yl)benzonitrile To a stirred solution of 3-bromo-5-(trifluoromethyl)benzonitrile (0.5 g, 2.0 mmol) in DMF (10 mL), 4-(trifluoromethyl)-1 H-pyrazole (355 mg, 2.6 mmol), Cesium carbonate (1.3 g, 4.0 mmol) and Copper iodide (77 mg, 0.40 mmol) were added at rt. The reaction mixture was purged with nitrogen for 15m in and then heated at 120°C in a sealed tube for 24 h. Then the reaction mass was diluted with EtOAc and passed through the bed of silica and concentrated to give the title compound in low to moderate yield. GCMS (Method E) 5.73 min, 305.1 (MH-).

Intermediate P: 3-cyclopropyl-5-(trifluoromethyl)benzonitrile To a solution of (300 mg, 1 .42 mmol) in THF (2 mL), 1 M BH3 in THF (5 mL) was added. The mixture was stirred at rt for 16h and concentrated. The residue was re dissolved in a solution of 1 % HCI (4N in dioxane) in methanol and heated at 50 °C for 2 h. Solvent was removed and redissolved in 1 % HCI in methanol to give the title compound in good yield. GCMS (Method E) 9.61 min, 214.1 (MH-) 3) Examples of the compounds according to the invention

Example 1 : N-(3, 5-bis(trifluoromethyl)benzyl)-1 -( pyrimidin-2-yl)-1 H-1,2, 4-triazole-5- carboxamide

To a solution of B (68 mg, 0.356 mmol) in DMF (1 ml) were added 3,5- bis(trifluoromethyl)benzylaminehydrochloride (99 mg, 0.356 mmol), PyBOP (185 mg, 0.356 mmol) and DIPEA (0.186 mL, 1.07 mmol). The reaction mixture was stirred at 45 °C for 16 h then quenched with water (30 mL) and extracted with EtOAc (3x30 mL). The organic extracts were dried (MgSO ₄ ) and concentrated in vacuo. The residue was chromatographed on silica eluting with PE: EtOAc gradient 9:1 to 0:1 , to give the title compound (20 mg, 12.6%) as a white solid. LCMS (Method A) 2.12 min, 415.1 (MH ); LogD 2.6. Examples 2, 5, 11, 12, 15 and 16-38

The following Examples were prepared using the general method described in Example 1 from the appropriate intermediates or commercial materials.

Example 3: N-( 1-(3, 5-bis(trifluoromethyl)phenyl)ethyl)-1-(pyridin-2-yl)-1H- 1, 2, 4- triazole-5-carboxamide To a solution of Intermediate D (170 mg, 0.518 mmol) in DMF (2 mL) was added A/ _; A/-dimethylformamide dimethyl acetal (0.083 mL, 0.622 mmol). The mixture was stirred at 70°C for 1 h and then concentrated under reduced pressure to give the corresponding amidine. A mixture of the amidine and 2-hydrazinopyridine (85 mg, 0.777 mmol) in acetic acid (2.0 mL) was stirred at 90°C overnight and then treated with EtOAc and sat. NaHCO ₃ (aq) solution. Solid NaHCO ₃ was used to adjust the pH to 7-8. The aqueous solution was extracted with EtOAc (2x30 ml). The organic extracts were dried (MgSO4) and concentrated in vacuo. The residue was chromatographed on silica eluting with PE: EtOAc gradient 9:1 to 0:1 to give an impure product. The afforded mixture was then chromatographed on NH ₂ functionalised silica eluting with PE: EtOAc gradient 9:1 to 8:2, to give the title compound (31 mg, 14%) as a white solid. LCMS (Method A) 2.40 min, 430.1 (MH ⁺ ). Examples 4, 6-10, 13, 14, and 39-65

The following Examples were prepared using the general method described in Example 3 from the appropriate intermediates or commercial materials.

To a mixture of N -(3,5-bis(trifluoromethyl)benzyl)-1 H-imidazole-2-carboxamide (100 mg, 0.30 mmol) and phenylboronic acid (36.2 mg, 0.30 mmol) in MeCN (3 ml) was added copper(ll) acetate (59 mg, 0.33 mmol), pyridine (0.048 ml, 0.59 mmol) and 4A° molecular sieves. The mixture was stirred at 60 °C overnight. The reaction mixture was filtered and concentrated. The residue was chromatographed on silica eluting with PE:EtOAc gradient 9:1 to 1 :4 to give the title compound in low to moderate yield. LCMS (Method C) 7.04 min, 414.1 (MH ⁺ ). logD 5.4.

To a stirred solution of example 42 (50 mg, 0.15 mmol) in CHCI ₃ (2 ml), m- chloroperbenzoic acid (53 mg, 0.31 mmol) was added portion wise at 0° C. The reaction mixture was stirred at rt for 2 h. 5% aq. Na2SO ₃ solution was added. The aqueous layer then extracted with DCM and washed with sat. aq. NaHCO ₃ solution. The combined organic layer was dried (Na2SO4) and concentrated. The residue was chromatographed on silica to give the title compound in moderate yield. LCMS (Method F) 2.35 min, 355.1 (MH ⁺ ). LogD 1.4

A sealed tube was charged with example 46 (150 mg, 0.35 mmol) in toluene (5 mL) and tributyl( 1 -ethoxyvinyl)tin (0.12 ml, 0.35 mmol). The solution was then degassed for 5 minutes and bis(triphenylphosphine)palladium chloride (25 mg, 0.035 mmol) was added at rt. The resulting solution was stirred at 100 °C for 12 h. The reaction mixture was cooled to rt, poured into cold water and extracted with EtOAc. The combined organic phase washed with brine, dried over Na2SO4, filtered and concentrated. Then 10%aq HCI was added to the crude and stirred at rt for 30 min. HCI was evaporated and crude material was purified using PREP-HPLC (Method G) to get the title compound in low to moderate yield. LCMS (Method F) 2.65 min, 389.1 (MH ⁺ ). LogD 3.5.

4) Biological examples

In the following, biological examples are shown which serve to illustrate the invention, but which are not understood as being limiting the scope of the invention. Certain compounds of the invention can be distinguished from known compounds by virtue of greater efficacy at low application rates, which can be verified by the person skilled in the art using the experimental procedures outlined in the Examples, using lower application rates if necessary, for example 100 ppm, 50 ppm, 25 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1 .5 ppm, 0.8 ppm or 0.2 ppm.

In particular, some compounds in accordance with the present invention were tested for their activity against Plutella xylostella and/or Myzus persicae.

Plutella xylostella: contact/feeding activity

Test compounds were diluted in an IF-50 water/tween solution. Cabbage leaf discs were immersed in the test solutions and dried. The dried leaves were placed in petri dishes containing a moistened piece of filter paper and infested with 5 second-instar diamondback moth larvae. The dishes were placed in a growth chamber for 4 days and percent mortality of the larvae recorded. The following compounds gave an effect of at least 80% control in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: 1 ,3,4,5,6,8,11 ,12,13,14,15,17,19,22,23,24,28,33,34,35,36,37,38,40,42,43,45 ,47,49, 52,53,54,57,58,59,68,69,70.

Myzus persicae: contact/feeding activity

Test compounds were diluted in an IF50 water/tween solution. Cabbage leaf discs were immersed in the test solutions for 2-3 seconds and placed on a wire screen to dry. The dried leaves were placed in a 24 well plate. The leaf discs were infested with an aphid population of mixed ages. The dishes were placed in a growth chamber for 5 days and percent mortality of the aphids recorded. The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: 4,6,11 ,12.

In summary, as demonstrated above, the novel compounds according to the present invention are effective against Plutella and Myzus. In addition, it is expected that the compounds according to the present invention and compositions comprising one or more of these compounds have an advantageous safety profile with respect to nontarget organisms including bees and do not show aquatoxicity.