EA047112B1 - MICROBIOCIDAL THIAZOLE DERIVATIVES - Google Patents

Description

The present invention relates to microbiocidal thiazole derivatives, such as active ingredients, for example, which have microbiocidal activity, in particular fungicidal activity. The present invention also relates to the preparation of such thiazole derivatives, to agrochemical compositions that contain at least one of the thiazole derivatives, and to applications of thiazole derivatives or compositions based thereon in agriculture or horticulture for the control or prevention of infection of plants harvested from food crops. crops, seeds or non-living materials by phytopathogenic microorganisms, mainly fungi.

WO 2010/012793 describes aminothiazole derivatives as pesticides.

According to the present invention there is provided a compound of formula (I)

where R ¹ represents chlorine or fluorine;

R ² represents hydrogen;

R ³ represents C _g C ₃ alkyl;

R ⁴ represents hydrogen;

R ⁵ represents hydrogen, halogen, C _g C ₆ alkyl, C ₂ -C6 alkenyl, C 2 -C ₆ alkynyl, C ₁ -C ₄ haloalkyl, C ₂ -C 6 haloalkenyl, C ₂ -C ₆ haloalkenyl, hydroxyC ₁ -C ₄ alkyl, cyanoC ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, phenyl or heteroaryl, where the heteroaryl moiety is a 5- or 6-membered aromatic monocyclic ring containing 1, 2, 3 or 4 heteroatoms, individually selected from nitrogen, oxygen and sulfur, and wherein each of the C ₃ -C ₆ cycloalkyl, phenyl and heteroaryl moieties is optionally substituted with 1-3 groups represented by R ⁷ ;

R ⁶ represents hydrogen, halogen, C _g C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₄ haloalkyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ haloalkynyl, hydroxyC ₁ -C ₄ alkyl, cyanoC ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, phenyl or heteroaryl, where the heteroaryl fragment is a 5- or 6-membered aromatic monocyclic ring containing 1, 2, 3 or 4 heteroatoms, according to separately selected from nitrogen, oxygen and sulfur, and wherein each of the C3-C6 cycloalkyl, phenyl and heteroaryl moieties is optionally substituted with 1-3 groups represented by R ⁷ ;

R ⁷ represents halogen, cyano, _hydroxyl , _CrC3alkyl , CrClkoxy or _C3 - _C4cycloalkyl ;

X represents C-H;

or a salt or N-oxide thereof.

Surprisingly, it has been found that the new compounds of formula (I) have, for practical purposes, a very effective level of biological activity for protecting plants from diseases that are caused by fungi.

In accordance with a second aspect of the present invention, there is provided an agrochemical composition containing a fungicidal effective amount of a compound of formula (I) in accordance with the present invention. Such a composition for agricultural use may further contain at least one additional active ingredient and/or an agrochemically acceptable diluent or carrier.

According to a third aspect of the present invention, there is provided a method for controlling or preventing infection of beneficial plants by phytopathogenic microorganisms, wherein a fungicidal effective amount of a compound of formula (I) or a composition containing the compound as an active ingredient is applied to the plants, parts thereof or their habitat.

According to a fourth aspect of the present invention, there is provided the use of a compound of formula (I) as a fungicide. In accordance with this particular aspect of the present invention, use may or may not include methods of treating a human or animal body through surgery or therapy.

When substituents are stated to be optionally substituted, this means that they may or may not bear one or more identical or different substituents, for example one, two or three R ⁷ substituents. For example, C ₁ -C ₆ alkyl substituted with 1, 2 or 3 halogen atoms may include, without limitation, the groups -CH ₂ Cl, -CHCl ₂ , -CCl ₃ , -CH2F, -CHF2, -CF ₃ , -CH2CF3 or - CF2CH3. As another example, C ₁ -C ₆ alkoxy substituted with 1, 2 or 3 halogen atoms may include, but is not limited to, the groups CHC1-, CHC1 ₂ O-, CC1 ₃ O-, CH2FO-, CHF2O-, CF3O-, CF3CH2O- or CH3CF2O-.

As used herein, the term hydroxyl or hydroxy means a -OH group.

As used herein, the term cyano means a -CN group.

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As used herein, the term halogen refers to fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo).

The term S.'|-S.' used in this document ₆ alkyl refers to a straight or branched chain hydrocarbon radical consisting solely of carbon and hydrogen atoms, containing no unsaturated bonds, having from one to six carbon atoms, and which is attached to the rest of the molecule by a single bond. C-Clkyl and _C1 -C3alkyl should be interpreted accordingly. Examples of C ₁ -C ₆ alkyl include, but are not limited to, methyl, ethyl, n-propyl and isomers thereof, eg isopropyl.

As used herein, the term C ₁ -C ₄ alogenalkyl refers to a C ₁ -C ₄ alkyl radical, as generally defined above, substituted by one or more identical or different halogen atoms. Examples of C1- _C4 haloalkyl include, but are not limited to, trifluoromethyl.

As used herein, the term hydroxyC ₁ -C ₄ alkyl refers to a C 1 -C ₄ alkyl radical, as generally defined above, substituted by one or more hydroxy groups.

As used herein, the term cyanoC ₁ -C ₄ alkyl refers to a C ₁ -C ₄ alkyl radical, as generally defined above, substituted by one or more cyano groups.

As used herein, the term C ₂ -C ₆ alkenyl refers to a group that is a straight or branched chain hydrocarbon radical consisting solely of carbon and hydrogen atoms containing at least one double bond, which can be located either in (E)- , or in the (2) configuration, having from two to six carbon atoms, which is attached to the rest of the molecule by a single bond. The term C ₂ -C 3 alkenyl should be interpreted accordingly. Examples of C ₂ -C ₆ alkenyl include, but are not limited to, ethenyl (vinyl), prop-1-enyl, prop-2-enyl (allyl), but-1-enyl.

As used herein, the term C ₂ -C ₆ alkynyl refers to a group that is a straight or branched chain hydrocarbon radical consisting solely of carbon and hydrogen atoms, containing at least one triple bond having from two to six carbon atoms, and which is attached to the rest of the molecule by a single bond. The term _C2C3alkynyl should be interpreted accordingly. Examples of C ₂ -C ₆ alkynyl include, but are not limited to, ethynyl, prop-1-ynyl, but-1-ynyl.

As used herein, the term C ₂ -C ₆ haloalkenyl refers to a C ₂ -C ₆ alkenyl radical, as generally defined above, substituted by one or more identical or different halogen atoms. Examples of C ₂ -C ₆ haloalkenyl include, but are not limited to, 2-fluorovinyl, 2,2-difluorovinyl, 2-vinyl chloride and 2,2-dichlorovinyl.

As used herein, the term C ₂ -C ₆ haloalkynyl refers to a C ₂ -C ₆ alkynyl radical, as generally defined above, substituted by one or more identical or different halogen atoms.

As used herein, the term C1- _C4 alkoxy refers to a radical of the formula -ORa, where Ra is a C1- _C4 alkyl radical as generally defined above. C1-C3 Alkoxy should be interpreted accordingly. Examples of C1- _C4 alkoxy include, but are not limited to, methoxy, ethoxy, 1-methylethoxy (isopropoxy), and propoxy.

As used herein, the term C3- _C6 cycloalkyl refers to a radical that is a monocyclic saturated ring system and that contains 3-6 carbon atoms. The term C ₃ -C ₄ cycloalkyl should be interpreted accordingly. Examples of C ₃ C ₆ cycloalkyl include, but are not limited to, cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, cyclobutyl, 1-methylcyclobutyl, 1,1-dimethylcyclobutyl, 2-methylcyclobutyl, and 2,2-dimethylcyclobutyl.

As used herein, the term heteroaryl refers to a 5- or 6-membered aromatic monocyclic ring radical that contains 1, 2, 3 or 4 heteroatoms selected individually from nitrogen, oxygen and sulfur. Examples of heteroaryl include, but are not limited to, furanyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl, or pyridyl.

The presence of one or more possible asymmetric carbon atoms in a compound of formula (I) means that the compounds may occur in optically isomeric forms, i.e. enantiomeric or diastereomeric forms. Atropoisomers may also occur as a result of limited rotation around a single bond. Formula (I) is intended to include all such possible isomeric forms and mixtures thereof. The present invention includes all such possible isomeric forms of the compound of formula (I) and mixtures thereof. Likewise, formula (I) is intended to include all possible tautomers. The present invention includes all possible tautomeric forms of the compound of formula (I).

In each case, the compounds of formula (I) according to the present invention are in free form, in oxidized form as an N-oxide or in salt form, for example an agronomically useful salt.

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

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The following list provides definitions, including preferred definitions, for the substituents R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and X with reference to the compounds of formula (I). With respect to any of these substituents, any of the definitions given below can be combined with any of the definitions of any other substituent given below or elsewhere in this document.

R ¹ is chlorine or fluorine, and most preferably fluorine.

R ² represents hydrogen.

R ³ is C1-C ₃ alkyl, preferably R ³ is methyl.

R ⁴ represents hydrogen.

R ⁵ represents hydrogen, halogen, C-C^alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C1-C ₄ haloalkyl, C 2 -C ₆ haloalkenyl, C _{2 -C 6} haloalkynyl, hydroxyC1- C ₄ alkyl, cyanoC ₁ -C ₄ alkyl, C ₃ -C ₆ cycloalkyl, phenyl or heteroaryl, where the heteroaryl moiety is a 5- or 6-membered aromatic monocyclic ring containing 1, 2, 3 or 4 heteroatoms, individually selected of nitrogen, oxygen and sulfur, and wherein each of the C3-C6 cycloalkyl, phenyl and heteroaryl moieties is optionally substituted with 1-3 groups represented by R ⁷ .

Preferably, R ⁵ is hydrogen, halogen, C^C^alkyl, C2-C6 alkynyl, C3-C4 cycloalkyl or phenyl, wherein each of the C3-C4 cycloalkyl and phenyl moieties is optionally substituted with 1-3 groups represented by R ⁷ . More preferably, R ⁵ is hydrogen, halogen, C.'|-C3 alkyl. C ₂ -C ₃ alkynyl or phenyl, wherein the phenyl moiety is optionally substituted with 1 or 2 groups represented by R ⁷ . Even more preferably, R ⁵ is hydrogen, chlorine, fluorine, bromine, methyl, ethyl, isopropyl, prop-2-ynyl or phenyl, wherein the phenyl moiety is optionally substituted with 1 or 2 groups represented by R ⁷ . Still more preferably, R ⁵ is hydrogen, chlorine, fluorine, methyl, ethyl, prop-2-ynyl, phenyl, 4-fluorophenyl or 4-chlorophenyl, and most preferably hydrogen or methyl.

R ⁶ represents hydrogen, halogen, C1- _C6 alkyl, C2- _C6 alkenyl, _C2 - _C6 alkynyl, _C1 - _C4 haloalkyl, C2- _C6 haloalkenyl, _{C2 - C6} haloalkynyl, hydroxyC1- C ₄ alkyl, cyanoC1-C ₄ alkyl, C ₃ -C ₆ cycloalkyl, phenyl or heteroaryl, where the heteroaryl moiety is a 5- or 6-membered aromatic monocyclic ring containing 1, 2, 3 or 4 heteroatoms, individually selected from nitrogen, oxygen and sulfur, and wherein each of the C ₃ -C ₆ cycloalkyl, phenyl and heteroaryl moieties is optionally substituted with 1-3 groups represented by R ⁷ .

Preferably ^R6 is hydrogen, halogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl or phenyl, where the heteroaryl moiety is a 5- or 6-membered aromatic monocyclic ring containing 1, 2 or 3 heteroatoms, individually selected from nitrogen, oxygen and sulfur, and wherein each of the C3-C6 cycloalkyl, phenyl and heteroaryl moieties is optionally substituted with 1-3 groups represented by R ⁷ . More preferably, R ⁶ is hydrogen, halogen, C1-C3alkyl, C2-C3alkenyl, C2-C3alkynyl, C3-C4cycloalkyl, phenyl or heteroaryl, where the heteroaryl moiety is a 5-membered aromatic monocyclic ring containing 1 or 2 heteroatoms, individually selected from nitrogen, oxygen and sulfur, and wherein each of the C3- _C4 cycloalkyl, phenyl and heteroaryl moieties is optionally substituted with 1 or 2 groups represented by ^R7 . Even more preferably, R ⁶ is hydrogen, chloro, fluorine, bromo, methyl, ethyl, isopropyl, prop-2-enyl, prop-2-ynyl, cyclopropyl, cyclobutyl, phenyl or thienyl, wherein each of the phenyl and thienyl moieties is optionally substituted 1 or 2 groups represented by R ⁷ . Still more preferably, R ⁶ is hydrogen, chlorine, fluorine, methyl, ethyl, prop-2-enyl, prop-2-ynyl, cyclopropyl, cyclobutyl, phenyl, 4-fluorophenyl, 2,4-difluorophenyl, 4-chlorophenyl, 2 ,4-dichlorophenyl or 3-methyl-2-thienyl and most preferably methyl, 2,4-difluorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl or 3-methyl-2-thienyl.

R ⁷ is halogen, cyano, hydroxyl, C1-C3alkyl, C1-C3alkoxy or C3-C4cycloalkyl. Preferably R ⁷ is halogen, C1-C3 alkyl or C1-C ₃ alkoxy, more preferably chlorine, fluorine, bromine, methyl, ethyl, isopropyl, methoxy, ethoxy or isopropoxy, even more preferably chlorine, fluorine, bromine, methyl or ethyl. Still more preferably, R ⁷ is chlorine, fluorine or methyl.

In one embodiment, when R ⁵ is hydrogen or C1-C3 alkyl, R ⁶ is C1-C ₃ alkyl, phenyl or thienyl, wherein each of the phenyl and thienyl moieties is optionally substituted with 1 or 2 groups selected from R ⁷ . Preferably, when R ⁵ is hydrogen or methyl, R ⁶ is C1-C ₃ alkyl, phenyl or thienyl, wherein each of the phenyl and thienyl moieties is optionally substituted with 1 or 2 groups selected from R ⁷ . More preferably, when R ⁵ is hydrogen or methyl, R ⁶ is methyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,4-difluorophenyl or 3-methyl-2-thienyl.

X represents C-H.

In the compound of formula (I) according to the present invention, it is preferable

R ¹ represents chlorine or fluorine;

R ² and R ⁴ are each independently hydrogen;

R ³ represents C1-C ₃ alkyl;

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R ⁵ represents hydrogen, halogen, ^-C^alkyl, C ₂ -C ₃ alkynyl or phenyl, where the phenyl moiety is optionally substituted with 1 or 2 groups represented by R ⁷ ;

R ⁶ represents hydrogen, halogen, ^-^alkyl, C ₂ -C ₃ alkenyl, C ₂ -C ₃ alkynyl, phenyl or heteroaryl, where the heteroaryl moiety is a 5-membered aromatic monocyclic ring containing 1 sulfur atom, and where each of the phenyl and heteroaryl moieties is optionally substituted with 1 or 2 groups represented by R ⁷ ; R ⁷ is chlorine, fluorine, bromine, methyl, ethyl, isopropyl, methoxy, ethoxy or isopropoxy; And

X represents C-H.

The compounds of formula (I) in accordance with the present invention may have two chiral centers at carbon atoms A and B, as indicated below in formula (A)

Accordingly, as already indicated, the compounds of formula (I) can exist in various diastereomeric forms, i.e. with (S,S)-, (S,R)-, (R,R)- or ^^-configurations represented at carbon atoms A and B, respectively. In particular, each of such configurations may be apparent for compounds of formula (I) with respect to specific combinations of definitions for R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and X for each compound described in table 1 (from compounds of formulas (1.i.01-1.a.32) to compounds of formulas (1.z.01 - 1.Z.32)), or compounds of formula (I) described in table. 2 (below).

The compounds of the present invention can be prepared as shown in the following diagrams, in which, unless otherwise indicated, the definition of each variable is as defined above for the compound of formula (I).

The compounds of formula (I) according to the present invention, wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and X are as defined for formula (I), can be prepared by converting the compound of formula (II ), where R ¹ , R ² and X are as defined for formula (I), using a compound of formula (III), where R ³ , R ⁴ , R ⁵ and R ⁶ are as defined for formula (I ), and R ⁸ is bromine or iodine, either by thermal heating, a base, or under transition metal-catalyzed Buchwald-Hartwig amination conditions. This is shown in Diagram 1 below.

Scheme 1

Compounds of formula (III) wherein R ³ , R ⁴ , R ⁵ and R ⁶ are as defined for formula (I) and R ⁸ is bromine or iodine can be prepared by converting a compound of formula (IV) where R ³ is as defined for formula (I), and R ⁸ is bromine or iodo, and compounds of formula (V), wherein R ⁴ , R ⁵ and R ⁶ are as defined for formula (I), and with using a peptide agent involved in the coupling reaction. This is shown in Diagram 2 below.

Scheme 2

Alternatively, compounds of formula (III) wherein R ³ , R ⁴ , R ⁵ and R ⁶ are as defined for formula (I) and R ⁸ is bromine or iodine can be prepared by converting a compound of formula (VI) wherein R ³ is as defined for formula (I), R ⁸ is bromine or iodine, and R ⁹ is fluorine or chlorine, and compounds of formula (V) wherein R ⁴ , R ⁵ and R ⁶ are such , as defined for formula (I), and using a base. This is shown in diagram 3 below.

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Scheme 3

Compounds of formula (IV) wherein R ³ is as defined for formula (I) and R ⁸ is bromine or iodine can be prepared by converting a compound of formula (VII) wherein R ³ is as defined for formula ( I), R ⁸ represents bromine or iodine, and R ¹⁰ represents CrC^kil, and using a base. This is shown in diagram 4.

Scheme 4

Compounds of formula (VI) wherein R ³ is as defined for formula (I), R ⁸ is bromine or iodine, and R ⁹ is fluorine or chlorine can be prepared by converting a compound of formula (IV) wherein R ³ is as defined for formula (I), R ⁸ is bromine or iodine, and with a halogenating agent. This is shown in diagram 5.

Scheme 5

Alternatively, compounds of formula (I) wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and X are as defined for formula (I) can be prepared by converting a compound of formula (VIII) where R ¹ , R ² , R ³ and X are as defined for formula (I), using a compound of formula (V), where R ⁴ , R ⁵ and R ⁶ are as defined for formula (I), and with the help of a peptide agent participating in the coupling reaction. This is shown in diagram 6.

Scheme 6

Alternatively, compounds of formula (I) wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and X are as defined for formula (I) can be prepared by converting a compound of formula (IX) wherein R ¹ , R ² , R ³ and X are as defined for formula (I), and R ⁹ is fluorine or chlorine, using a compound of formula (V) where R ⁴ , R ⁵ and R ⁶ are as follows , as defined for formula (I), and using a base. This is shown in diagram 7.

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Scheme 7

Compounds of formula (VIII) wherein R ¹ , R ² , R ³ and X are as defined for formula (I) can be prepared by converting a compound of formula (X) wherein R ¹ , R ² , R ³ and X are as defined for formula (I), and R ¹⁰ represents C1-C ₆ alkyl, and with a base. This is shown in diagram 8.

Scheme 8

Compounds of formula (IX) wherein R ¹ , R ² , R ³ and X are as defined for formula (I) and R ⁹ is fluorine or chlorine can be prepared by converting a compound of formula (VIII) where R ¹ , R ² , R ³ and X are as defined for formula (I), and using a halogenating agent. This is shown in diagram 9.

Scheme 9 f he FR ⁹

The compounds of formula (X) according to the present invention, wherein R ¹ , R ² , R ³ and X are as defined for formula (I) and R ¹⁰ is C 1 -C 6 alkyl, can be prepared by converting a compound of formula (II ), where R ¹ , R ² and X are as defined for formula (I), using a compound of formula (XI), where R ³ is as defined for formula (I), R ⁸ is bromine or iodine , and R ¹⁰ is C1-C6 alkyl, either by thermal heating, a base, or under Buchwald-Hartwig transition metal-catalyzed amination conditions. This is shown in diagram 10.

Scheme 10

Alternatively, compounds of formula (X), wherein R ¹ , R ² , R ³ and X are as defined for formula (I), and R ¹⁰ represents C 1 -C 6 alkyl, can be prepared by converting a compound of formula (XII), where R ¹ and X are as defined for formula (I), and R ⁸ is bromine or iodine, using a compound of formula (XIII), where R ² and R ³ are as defined for formula (I), and R ¹⁰ is C1-C6 alkyl, under transition metal catalyzed Buchwald-Hartwig amination conditions. This is shown in diagram 11.

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Scheme 11

Alternatively, the compounds of formula (I) according to the present invention, wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and X are as defined for formula (I), can be prepared by converting the compound formula (XII), where R ¹ and X are as defined for formula (I), and R ⁸ represents bromine or iodine, using a compound of formula (XIV), where R ² , R ³ , R ⁴ , R ⁵ , and R ⁶ are as defined for formula (I), under the conditions of transition metal catalyzed Buchwald-Hartwig amination. This is shown in diagram 12.

Scheme 12

Surprisingly, it has been found in this work that the new compounds of formula (I) have, for practical purposes, a very effective level of biological activity for protecting plants from diseases that are caused by fungi.

The compounds of formula (I) can be used in agriculture and related applications, for example, as active ingredients for the control of plant pests or on non-living materials for the control of spoilage microorganisms or organisms potentially harmful to humans. The new compounds have excellent activity at low application rates, are well tolerated by plants and are safe for the environment. They are characterized by very useful therapeutic, preventive and systemic properties and can be used to protect numerous cultivated plants. The compounds of formula (I) can be used to suppress or destroy pests that occur on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of various agricultural crops that are beneficial plants, while at the same time protecting those plant parts which develop later, for example, from phytopathogenic microorganisms.

The present invention further relates to a method for controlling or preventing infestation of plants or plant propagation material and/or harvested food crops susceptible to microbial attack by treating the plants or plant propagation material and/or harvested food crop, wherein an effective amount of a compound of formula (I) is applied to plants, parts thereof or where they grow.

Also, the compounds of formula (I) can be used as a fungicide. As used herein, the term fungicide means a compound that controls, modifies or prevents the growth of fungi. The term fungicidal effective amount means an amount of such a compound or combination of such compounds that is capable of having an effect on the growth of fungi. Controlling or modifying effects include all deviations from natural development, such as killing, inhibition of development, etc., and prevention includes a barrier or other protective formation in or on the plant to prevent fungal infection.

Also, the compounds of formula (I) can be used as dressing agents for the purpose of treating plant propagation material, for example seeds, for example fruits, tubers or grains, or plant shoots (for example rice), to protect against fungal infections, and also from phytopathogenic fungi found in the soil. The propagation material can be treated with a composition containing a compound of formula (I) before planting: the seed, for example, can be treated before sowing.

The active ingredients of the present invention can also be applied to grains (coating), either by impregnating the seeds in a liquid composition or by coating them with a solid composition. The composition can also be applied to a planting site during planting of propagation material, for example, to a seed furrow during sowing. A real invention

- 7 047112 This also applies to such methods of processing plant propagation material and to plant propagation material processed in this way.

Moreover, the compounds in accordance with the present invention can be used for the control of fungi in related fields, for example, in the field of protection of technical materials, including wood and wood-related technical products, in the field of food storage, in the field of sanitary processing.

In addition, the present invention can be used to protect non-living materials from fungal attack, such as lumber, siding and paint.

The compounds of formula (I) can, for example, be effective against fungi and fungal disease vectors, as well as against phytopathogenic bacteria and viruses. These fungi and fungal disease vectors, as well as phytopathogenic bacteria and viruses, are, for example:

Absidia corymbifera, Alternaria spp, Aphanomyces spp, Ascochyta spp., Aspergillus spp., including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terms, Aureobasidium spp., including A. pullulans, Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp., including B. dothidea, B. obtusa, Botrytis spp., including B. cinerea, Candida spp., including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis, Cephaloascus fragrans, Ceratocystis spp., Cercospora spp., including C. arachidicola, Cercosporidium personatum, Cladosporium spp, Claviceps purpurea, Coccidioides immitis, Cochliobolus spp., Colletotrichum spp., including C. musae, Cryptococcus neoformans, Diaporthe spp., Didymella spp., Drechslera spp., Elsinoe spp., Epidermophyton spp., Erwinia amylovora, Erysiphe spp., including E. cichoracearum, Eutypa lata, Fusarium spp., including F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, F. solani, Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, Helminthosporium spp., Hemileia spp., Histoplasma spp., including H. capsulatum, isaria fuciformis , Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochium nivale, Microsporum spp., Monilinia spp., Mucor spp., Mycosphaerella spp., including M. graminicola, M. pomi, Oncobasidium theobromaeon, Ophiostoma piceae, Paracoccidioides spp., Penicillium spp., including P. digitatum, P. italicum, Petriellidium spp., Peronosclerospora spp., including P. maydis, P. philippinensis and P. sorghi, Peronospora spp., Phaeosphaeria nodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp., Phoma spp., Phomopsis viticola, Phytophthora spp., including P. infestans, Plasmopara spp., including P. halstedii, P. viticola, Pleospora spp., Podosphaera spp., including P. leucotricha, Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp., Pseudoperonospora spp., including P. hordei, P. recondita, P. striiformis, P. triticina , Pyrenopeziza spp., Pyrenophora spp., Pyricularia spp., including P. cubensis, P. humuli, Pseudopeziza tracheiphila, Puccinia spp., including P. oryzae, Pythium spp., including P. ultimum, Ramularia spp., Rhizoctonia spp., Rhizomucor pusillus, Rhizopus arrhizus, Rhynchosporium spp., Scedosporium spp., including S. apiospermum and S. proliftcans, Schizothyrium pomi, Sclerotinia spp., Sclerotium spp., Septoria spp., including S. nodorum, S. tritici, Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp., Stagonospora nodorum, Stemphylium spp., Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilletia spp., Trichoderma spp., including T harzianum, T. pseudokoningii, T. viride, Trichophyton spp., Typhula spp., Uncinula necator, Urocystis spp., Ustilago spp., Venturia spp., including V. inaequalis, Verticillium spp. and Xanthomonas spp.

Within the scope of the present invention, target crops and/or useful plants

- 8 047112 The crops to be protected generally include perennial and annual crops such as berry plants, for example varieties of blackberries, blueberries, cranberries, raspberries and strawberries; grains, such as barley, maize (corn), millet, varieties of oats, rice, rye, sorghum, triticale and wheat; fibrous plants such as cotton, flax, hemp, jute and sisal; field crops such as sugar beet, fodder beet, coffee tree, hops, mustard, oilseed rape (canola), poppy, sugar cane, sunflower, tea bush and tobacco; fruit trees such as apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; grasses such as Bermuda grass, bluegrass, bentgrass, Eremochloa serpentine, fescue, ryegrass, Augustine grass and Japanese zoysia; herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes, such as varieties of beans, lentils, peas and soybeans; nuts such as almonds, cashews, groundnuts, hazelnuts, peanuts, pecans, pistachio and walnuts; palm trees, such as oil palm; ornamental plants such as flowers, shrubs and trees; other trees such as cocoa tree, coconut tree, olive tree and rubber tree; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumber, garlic, lettuce, zucchini, melon, okra, onions, peppers, potatoes, pumpkin, rhubarb, spinach and tomato; as well as grape varieties, for example, varieties of grapes.

The term beneficial plants should be understood to also include beneficial plants that have been rendered tolerant to bromoxynil-like herbicides or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example, primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol- pyrovyl-shikimate-3-phosphate synthase), GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen oxidase) inhibitors) as a result of traditional breeding methods or genetic engineering. An example of a crop that has been made tolerant to imidazolinones, such as imazamox, through traditional breeding techniques (mutagenesis) is Clearfield® rapeseed (canola). Examples of crops that have been made tolerant to herbicides or classes of herbicides through genetic engineering techniques include glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady®, Herculex I® and LibertyLink®.

The term beneficial plants should be understood to also include beneficial plants that have been transformed by the use of recombinant DNA techniques such that they are capable of synthesizing one or more selective toxins such as those known, for example, from toxin-producing bacteria, especially bacteria of the genus Bacillus.

Examples of such plants are YieldGard® (a maize variety expressing the CryIA(b) toxin); YieldGard Rootworm® (maize variety expressing CryIIIB(b1) toxin); YieldGard Plus® (maize variety expressing CryIA(b) toxin and CryIIIB(b1) toxin); Starlink® (a maize variety expressing the Cry9(c) toxin); Herculex I® (a maize variety expressing the CryIF(a2) toxin and the enzyme phosphinothricin-Nacetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety expressing CryIA(c) toxin); Bollgard I® (cotton variety expressing CryIA(c) toxin); Bollgard II® (cotton variety expressing CryIA(c) toxin and CryIIA(b) toxin); VIPCOT® (cotton variety expressing VIP toxin); NewLeaf® (potato variety expressing CryIIIA toxin); NatureGard® Agrisure® GT Advantage (GA21 with glyphosate tolerance trait), Agrisure® CB Advantage (Bt11 with corn borer (CB) resistance trait), Agrisure® RW (with Western corn rootworm resistance trait) and Protecta®.

The term crops should be understood to also include crop plants that have been transformed by recombinant DNA techniques in such a way that they are capable of synthesizing one or more selective toxins such as those known, for example, from toxin-producing bacteria, especially bacteria of the genus Bacillus.

Toxins that may be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as 5-endotoxins, for example Cry1Ab, Cry1Ac, CrylF, Cry1Fa2, Cry2Ab, Cry3. Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vips), for example Vipl, Vip2, Vip3 or Vip3A; or insecticidal proteins from bacteria colonizing nematodes, such as Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi such as Streptomycetes toxins, plant lectins such as pea lectins, barley lectins or snowdrop lectins; agglutinins; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome inactivating proteins (RIPs), such as ricin, maize RIP, abrin, luffin, saporin or bryodin; steroid metabolic enzymes such as 3hydroxysteroid oxidase, ecdysteroid UDP-glycosyltransferase, cholesterol oxidases, inhibitors

- 9 047112 ecdysone, HMG-COA reductase, ion channel blockers such as sodium or calcium channel blockers, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, dibenzyl synthase, chitinases and glucanases.

In the context of the present invention, under 5-endotoxins, for example, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3. Cry3Bb1 or Сгу9С. or vegetative insecticidal proteins (Vips), for example Vip1, Vip2, Vip3 or Vip3A, are definitely also to be understood as hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinantly using a new combination of different domains of these proteins (see, for example, WO 02/15701). Truncated toxins are known, for example, truncated CrylAb. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are substituted. With such amino acid substitutions, sequences recognized by proteases that are not present in the natural toxin are preferably introduced into the toxin, for example, in the case of Cry3A055, a sequence recognized by cathepsin C is introduced into the Cry3 toxin (see WO 03/018810).

Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in EP-A-0374753, WO 93/07278, WO 95/34656, EP-A-0427529, EP-A-451878 and WO 03/052073.

Methods for producing such transgenic plants are generally known to one skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0367474, EP-A-0401979 and WO 90/13651.

The toxin contained in transgenic plants gives the plants resistance to harmful insects. Such insects can belong to any taxonomic group of insects, but are especially common among beetles (Coleoptera), dipterans (Diptera) and butterflies (Lepidoptera).

Transgenic plants containing one or more genes that encode insect resistance and express one or more toxins are known, and some of them are commercially available. Examples of such plants are: YieldGard® (a maize variety expressing the CryIAb toxin); YieldGard Rootworm® (a maize variety expressing the Cry3Bb1 toxin); YieldGard Plus® (maize variety expressing Cry1Ab toxin and Cry3Bb1 toxin); Starlink® (a maize variety expressing the Cry9C toxin); Herculex I® (a maize variety expressing the Cry1Fa2 toxin and the enzyme phosphinothricin-Nacetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety expressing Cry1Ac toxin); Bollgard I® (cotton variety expressing the Cry1Ac toxin); Bollgard II® (cotton variety expressing Cly1Ac toxin and Cry2Ab toxin); VipCot® (cotton variety expressing Vip3A toxin and Cry1Ab toxin); NewLeaf® (potato variety expressing the Cry3A toxin); NatureGard® Agrisure® GT Advantage (GA21 with glyphosate tolerance trait), Agrisure® CB Advantage (Bt11 with corn borer (CB) tolerance trait) and Protecta®.

Additional examples of such transgenic crops are the following.

1. Maize Bt11 from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 Saint-Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays that has been rendered resistant to corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated Cry1Ab toxin. Btll maize also transgenically expresses the PAT enzyme to provide tolerance to the herbicide glufosinate ammonium.

2. Maize Bt176 from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 Saint-Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays that has been rendered resistant to corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of the Cry1Ab toxin. Bt176 maize also transgenically expresses the PAT enzyme to provide tolerance to the herbicide glufosinate ammonium.

3. Maize MIR604 from Syngenta Seeds SAS, chemin de l'Hobit 27, F-31 790 Saint-Sauveur, France, registration number C/FR/96/05/10. Maize that has been rendered resistant to insects by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a sequence recognized by the protease cathepsin G. The production of such transgenic maize plants is described in WO 03/018810.

4. Maize MON 863 from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses the Cry3Bb1 toxin and is resistant to several insects of the order Coleoptera.

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

6. Maize 1507 from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C/NL/00/10. Genetically modified maize to express the Cry1F protein, providing resistance to some insects from the order Lepidoptera, and the PAT protein, providing tolerance to the herbicide glufosinate ammonium.

- 10 047112

7. Maize NK603xMON 810 from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03. Consists of hybrid maize varieties, traditionally bred by crossing the genetically modified varieties NK603 and M0N 810. Maize NK603xM0N 810 transgenically expresses the CP4 EPSPS protein, derived from Agrobacterium sp., strain CP4, which confers tolerance to the herbicide Roundup® (contains glyphosate), as well as Cry1Ab toxin derived from Bacillus thuringiensis subsp. kurstaki, which provides tolerance to some members of the order Lepidoptera, including the corn borer.

The term growing site as used herein means the fields in or on which plants are grown, or where the seeds of cultivated plants are sown, or where the seeds will be placed in the soil. It includes soil, seeds and seedlings, and existing green plants.

The term plant refers to all the physical parts of a plant, including seeds, seedlings, shoots, roots, tubers, stems, petioles, leaves and fruits.

The term plant propagation material is understood to mean the generative organs of a plant, such as seeds that can be used for propagation of the plant, and vegetative material, such as shoots or tubers, for example, potatoes. Mention may be made here of, for example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and plant parts. We can also mention sprouted plants and young plants that should be replanted after germination or after emerging from the soil. These young plants can be protected until transplanting by full or partial dipping treatment. Preferably, plant propagation material should be understood to mean seeds.

The pesticides referred to herein by their common names are known, for example, from The Pesticide Manual, 15th Ed., British Crop Protection Council 2009.

The compounds of formula (I) can be used in unmodified form or, preferably, together with auxiliary substances conventionally used in the field of formulation. Therefore, for convenience, they can be formulated by a known method into emulsifiable concentrates, applied as paste coatings, directly sprayed or diluted solutions or suspensions, diluted emulsions, wettable powders, soluble powders, dust preparations, granulates, as well as encapsulated forms, e.g. in polymeric substances. As with the type of compositions, methods of application, such as atomization, fine mist, dusting, diffusing, coating or watering, are selected in accordance with the intended purposes and prevailing conditions. The compositions may also contain additional auxiliary substances such as stabilizers, antifoams, viscosity regulators, binders or tackifiers, as well as fertilizers, micronutrient donors or other compositions to obtain special effects.

Suitable carriers and auxiliaries, for example for agricultural use, may be solid or liquid and are substances suitable in formulation technology, for example natural or regenerated minerals, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are, for example, described in WO 97/33890.

The compounds of formula (I) are usually used in the form of compositions and can be applied to the crop area or plant to be treated, simultaneously or sequentially with additional compounds. Such additional compounds may be, for example, fertilizers, or micronutrient donors, or other drugs that affect plant growth. They may also be selective herbicides or non-selective herbicides, as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if necessary together with additional carriers, surfactants or application aids commonly used in the field. compilation.

The compounds of formula (I) can be used in the form of (fungicidal) compositions for the control or protection against phytopathogenic microorganisms containing as active ingredient at least one compound of formula (I) or at least one preferred individual compound as defined above in free form or in the form of an agrochemically usable salt and at least one of the above auxiliary substances.

The present invention provides a composition, preferably a fungicidal composition, comprising at least one compound of formula (I), an agriculturally acceptable carrier and optionally an excipient. An agriculturally acceptable carrier is, for example, a carrier that is suitable for agricultural use. Agricultural media are well known in the art. Preferably, said composition may contain at least one or more pesticidal active compounds, for example, an additional fungicidal active ingredient in addition to the compound of formula (I).

- 11 047112

The compound of formula (I) may be the sole active ingredient of the composition or, if desired, it may be mixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator. The additional active ingredient may, in some cases, result in unexpected synergistic activities.

Examples of suitable additional active ingredients include the following: acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenic fungicides, aryl phenyl ketone fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole group fungicides, benzothiazole group fungicides, plant fungicides, bridged biphenyl group fungicides, carbamate group fungicides, carbanyl group fungicides, conazole group fungicides, copper-containing fungicides, dicarboximide group fungicides, dinitrophenol group fungicides, dithiocarbamate fungicides, dithiolane group fungicides, furamide group fungicides , fungicides of the furanilide group, fungicides of the hydrazides group, fungicides of the imidazoles group, mercury-containing fungicides, fungicides of the morpholine group, fungicides of the organophosphorus group, fungicides of the organotin group, fungicides of the oxatiin group, fungicides of the oxazole group, fungicides of the phenylsulfonamide group, fungicides of the polysulfide group, pyrazole groups, fungicides of the pyridine group, fungicides of the pyrimidine group, fungicides of the pyrrole group, fungicides of the quaternary ammonium compounds group, fungicides of the quinoline group, fungicides of the quinone group, fungicides of the quinoxaline group, fungicides of the strobilurin group, fungicides of the sulfonanilide group, fungicides of the thiadiazole group, fungicides of the thiazole group ov, fungicides of the thiazolidine group, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides and zinc-containing fungicides.

Examples of suitable additional active ingredients also include the following: 3difluoromethyl-1-methyl-1H-pyrazol-4-carboxylic acid (9-dichloromethylene-1,2,3,4-tetrahydro-1,4methano-naphthalen-5-yl)amide, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid methoxy-[1methyl-2-(2,4,6-trichlorophenyl)ethyl]amide, 1-methyl-3-difluoromethyl-III-pyrazole-4- carboxylic acid (2dichloromethylene-3-ethyl-1-methylindan-4-yl)amide (1072957-71-1), 1-methyl-3-difluoromethyl-III-pyrazole-4carboxylic acid (4'-methylsulfanylbiphenyl-2-yl) amide, 1-methyl-3-difluoromethyl-4H-pyrazole-4carboxylic acid [2-(2,4-dichlorophenyl)-2-methoxy-1-methylethyl]amide, (5-chloro-2,4-dimethylpyridin-3yl) -(2,3,4-trimethoxy-6-methylphenyl)methanone, (5-bromo-4-chloro-2-methoxypyridin-3-yl)-(2,3,4-trimethoxy-6-methylphenyl)methanone, 2 -{2-[(E)-3-(2,6-dichlorophenyl)-1-methyl-prop-2-ene-(E)-ylideneaminooxymethyl]phenyl}-2-[(2)-methoxyimino]-N- methyl acetamide, 3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin3-yl]pyridine, (E)-Nmethyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxy -iminoacetamide, 4-bromo-2cyano-NX-dimethyl-6-trifluoromethylbenzimidazole-1-sulfonamide, a-[N(3-chloro-2,6-xylyl)-2methoxyacetamido]-y-butyrolactone, 4-chloro-2- cyano-N-dimethyl-5-p-tolylimidazole-1-sulfonamide, Nallyl-4,5-dimethyl-2-trimethylsilylthiophene-3-carboxamide, N(1-cyano-1,2-dimethylpropyl)-2-(2, 4dichlorophenoxy)propionamide, N(2-methoxy-5-pyridyl)cyclopropane carboxamide, (+,-)-cis-1-(4chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol , 2-(1-tert-butyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol1-yl)-propan-2-ol, 2',6'-dibromo-2-methyl -4-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazol-5-carboxanilide, 1-imidazolyl-1-(4'-chlorophenoxy)-3,3-dimethylbutan-2-one, methyl-(E)-2 -[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, methyl-(E)-2-[2-[6-(2-thioamidophenoxy)pyrimidin-4-yloxy] phenyl]-3-methoxyacrylate, methyl-(E)-2-[2-[6-(2-fluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, methyl-(E)-2-[2- [6-(2,6-difluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, methyl-(E)2-[2-[3-(pyrimidin-2-yloxy)phenoxy]phenyl]-3- methoxyacrylate, methyl-(E)-2-[2-[3-(5-methylpyrimidin2-yloxy)-phenoxy]phenyl]-3-methoxyacrylate, methyl-(E)-2-[2-[3-(phenyl- sulfonyloxy)phenoxy]phenyl3-methoxyacrylate, methyl-(E)-2-[2-[3-(4-nitrophenoxy)phenoxy]phenyl]-3-methoxyacrylate, methyl-(E)-2-[2phenoxyphenyl] -3 - methoxyacrylate, methyl-(E)-2-[2-(3,5-dimethylbenzoyl)pyrrol-1-yl]-3-methoxyacrylate, methyl-(E)-2-[2-(3-methoxyphenoxy)phenyl ]-3-methoxyacrylate, methyl-(E)-2-[2-(2-phenylethen-1-yl)-phenyl]3-methoxyacrylate, methyl-(E)-2-[2-(3,5-dichlorophenoxy )pyridin-3-yl]-3-methoxyacrylate, methyl-(E)-2-(2(3-(1,1,2,2-tetrafluoroethoxy)phenoxy)phenyl)-3-methoxyacrylate, methyl-(E) -2-(2-[3 -(alpha-hydroxybenzyl)phenoxy]phenyl)-3-methoxyacrylate, methyl-(E)-2-(2-(4-phenoxypyridin-2-yloxy)phenyl)-3-methoxyacrylate, methyl-(E)-2-[2-(3-n-propyloxy-phenoxy)phenyl] 3-methoxyacrylate, methyl-(E)-2-[2-(3 isopropyloxyphenoxy)phenyl]-3-methoxyacrylate, methyl- (E)-2-[2-[3 -(2-fluorophenoxy)phenoxy]phenyl]-3 methoxyacrylate, methyl-(E)-2-[2-(3-ethoxyphenoxy)phenyl]-3-methoxyacrylate, methyl- (E)-2-[2-(4-tert-butyl-pyridin-2-yloxy)phenyl]-3-methoxyacrylate, methyl-(E)-2-[2-[3-(3-cyanophenoxy)phenoxy]phenyl] 3-methoxyacrylate, methyl-(E)-2-[2-[(3 -methyl-pyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[6-(2- methyl-phenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, methyl-(E)-2-[2-(5-bromopyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate, methyl-(E)- 2-[2-(3-(3-iodopyridin-2-yloxy)phenoxy)phenyl]-3-methoxyacrylate, methyl-(E)-2-[2-[6-(2-chloropyridin-3 -yloxy)pyrimidine -4-yloxy]phenyl]-3 - 12 047112 methoxyacrylate, methyl-(E), (E)-2-[2-(5,6-dimethylpyrazin-2-ylmethyloxyminomethyl)phenyl]-3-methoxyacrylate, methyl-( E)-2-{2-[6-(6-methylpyridin-2-yloxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate, methyl-(E), (E)-2-{2-(3 -methoxyphenyl)methyloxyminomethyl]phenyl}-3-methoxyacrylate, methyl-(E)-2-{2-(6(2-azidophenoxy)-pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate, methyl-(E), (E)-2-{2-[6-phenylpyrimidin-4-yl)-methyloxyminomethyl]phenyl}-3-methoxyacrylate, methyl (E),(E)-2-{2-[(4-chlorophenyl)methyloxyminomethyl ]phenyl}-3-methoxyacrylate, methyl-(E)-2-{2-[6-(2-n-propylphenoxy)-1,3,5-triazin-4yloxy]phenyl}-3-methoxyacrylate, methyl-( E),(E)-2-{2-[(3-nitrophenyl)methyloxyminomethyl]phenyl}-3methoxyacrylate, 3-chloro-7-(2-aza-2,7,7-trimethyl-oct-3-ene- 5-yne), 2,6-dichloro-N-(4-trifluoromethylbenzyl)benzamide, 3-iodo-2-propynyl alcohol, 4-chlorophenyl-3-iodopropargyl formaldehyde, 3-bromo-2,3diiodo-2-propenylethylcarbamate, 2,3,3-triiododallyl alcohol, 3-bromo-2,3-diiodo-2-propenyl alcohol, 3 -iodo-2-propynyl-n-butylcarbamate, 3 -iodo-2-propynyl-n-hexylcarbamate, 3 - iodo-2-propynylcyclohexylcarbamate, 3-iodo-2-propynylphenylcarbamate; phenol derivatives such as tribromophenol, tetrachlorophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorphenol, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4-chlorophenol , 5-hydroxy-2(5H)-furanone; 4,5-dichlorodithiazolinone, 4,5-benzodithiazolinone, 4,5-trimethylenedithiazolinone, 4,5-dichloro-(3H)-1,2-dithiol-3-one, 3,5dimethyltetrahydro-1,3,5-thiadiazinone 2-thione, N(2-p-chlorobenzoylethyl)hexamine chloride, acibenzolar, acipetax, alanicarb, albendazole, aldimorph, allicin, allyl alcohol, ametoctradine, amisulbrom, amobam, ampropylphos, anilazine, asomat, aureofungin, azaconazole, azafendine, azithiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentaluron, benthiavalicarb, benthiazole, benzalkonium chloride, benzamacryl, benzomorph, benzohydroxamic acid, benzovindiflupyr, berberine, betoxazine, biloxazole, binapacryl, biphenyl, tertanol, bithionol, bixafen , blasticidin-S, boscalid, bromotalonil, bromuconazole, bupirimate, butiobate, butylamine, calcium polysulfide, captafol, captan, carbamorph, carbendazim, carbendazim hydrochloride, carboxin, carpropamide, carvone, CGA41396, CGA41397, quinomethionate, chitosan, chloraniforme, tan, chloranil , chlorphenazole, chloroneb, chloropicrin, chlorothalonil, chlorzolinate, chlozolinate, climbazole, clotrimazole, closilacone, copper-containing compounds such as copper acetate, copper carbonate, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper hydroxyquinolate, copper silicate, copper sulfate , copper tallate, copper and zinc chromate and Bordeaux mixture, cresol, kufraneb, cuprobam, copper oxide, cyazofamide, cyclofuramide, cycloheximide, cyflufenamide, cymoxanil, cipendazole, cyproconazole, cyprodinil, dazomet, debacarb, decafentine, dehydroacetic acid, di-2- pyridyl disulfide-1,1'-dioxide, dichlorfluanid, diclomesin, dichloran, dichloran, dichlorophen, dichlorozoline, diclobutrazol, diclocymet, diethofencarb, difenoconazole, difenzoquat, diflumetorim, O-di-isopropyl^-benzyl thiophosphate, dimefluazole, dimethachlon, dimethconazole , dimethomorph, dimethyrimol, diniconazole, diniconazole-M, dinobuton, dinocap, dinoctone, dinopentone, dinosulfone, dinoterbone, diphenylamine, dipyrithione, disulfiram, ditalifos, dithianone, dithioether, dodecyldimethylammonium chloride, dodemorph, dodicine, dodine, doguadine, edifenphos, , enestroburin, epoxiconazole, etaconazole, etem, etaboxam, ethirimol, ethoxyquin, ethylicin, ethyl-(2)-N-benzyl-N-([methyl(methylthioethylideneamino-oxycarbonyl)amino]thio)-β-alaninate, etridiazole, famoxadone, fenamidone , fenaminosulf, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamide, phenitropan, fenoxanil, fenpiclonil, fenpicoxamide, fenpropidine, fenpropimorph, fenpyrazamine, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, flupicolide, fluopyram, fluoroimide , fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutanil, flutolanil, flutriafol, fluxapyroxad, folpet, formaldehyde, fosetil, fuberidazole, furalaxyl, furamethpyr, furcarbanil, furconazole, furfural, furmecyclox, furofanate, , griseofulvin, guazatin, galacrinate, hexachlorobenzene , hexachlorobutadiene, hexachlorophene, hexaconazole, hexylthiophos, hydrargafen, hydroxyisoxazole, himexazole, imazalil, imazalil sulfate, imibenconazole, iminoctadine, iminoctadine triacetate, inesin, iodocarb, ipconazole, ipfentrifluconazole, iprobenfos, iprodione, carb, isopropanylbutylcarbamate, isoprothiolane, isopyrazam, isothianyl, isovaledione , isopamphos, kasugamycin, kresoxim-methyl, LY186054, LY211795, LY248908, mancozeb, mandipropamide, maneb, mebenil, mecarbinside, mefenoxam, mefentrifluconazole, mepanipyrim, mepronil, mercuric chloride, meptildinocap, , metalaxyl, metalaxyl-M, metam, metazoxolone , metconazole, metasulfocarb, metfuroxam, methyl bromide, methyl iodide, methyl isothiocyanate, metiram, methiram-zinc, metominostrobin, metrafenone, metsulfovax, milneb, moroxidine, myclobutanil, myclozoline, nabam, natamycin, neoasosin, nickel dimethyldithiocarbamate, ren, nitrotal-isopropyl, nuarimol, octilinone, ofuras, organomercury compounds, orysastrobin, osthole, oxadixil, oxasulfuron, oxathiapiproline, oxine-copper, oxolinic acid, oxpoconazole, oxycarboxin, parinol, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, penthiopyrad, phenamacryl, phenazine oxide, osdifene, fosetyl- A1, phosphoric acids, phthalide, picoxystrobin, piperalin, polycarbamate, polyoxin D, polyoxrim, polyram, probenazole, prochloraz, procymidone, propamidine, propamocarb, propiconazole, propineb, propionic acid, proquinazid, prothiocarb, prothioconazole, pidiflumetofen, pyracarbolide, pyraclostrobin, strobine , pyrooxystrobin, pyrazophos, pyribencarb, pyridinitrile, pyrifenox, pyrimethanil, pyriophenone, pyroquilone, piroxychlor, piroxifur, pyrrolnitrin, quaternary ammonium compounds, quinacetol, quina

- 13 047112 zamide, quinconazole, quinomethionate, quinoxifene, quintozene, rabenzazole, santonin, sedaxane, silthiofam, simeconazole, sipconazole, sodium pentachlorophenolate, spiroxamine, streptomycin, sulfur, sultropen, tebuconazole, tebfloquin, teklofthalam, teknazene, coram, tetraconazole, thiabendazole, thiadifluor, thiciofen, tifluzamide, 2-(thiocyanomethylthio)benzothiazole, thiophanate-methyl, thioquinox, thiram, tiadinil, timibenconazole, thioximide, tolclofos-methyl, tolylfluanide, triadimefon, triadimenol, triamiphos, triarimol, triazbutyl, triazoxide, zol, tridemorph, trifloxystrobin , triflumazole, triforin, triflumizole, triticonazole, uniconazole, urbacid, validamycin, valifenalate, vapam, vinclozolin, zarilamide, zineb, ciram and zoxamide.

The compounds of the present invention can also be used in combination with anthelmintics. Such anthelmintics include compounds selected from the class of macrocyclic lactone compounds, such as the derivatives of ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin, described in EP-357460, EP-444964 and EP-594291. Additional anthelmintics include semisynthetic and biosynthetic derivatives of avermectin/milbemycin, such as those described in US-5015630, WO-9415944 and WO-9522552. Additional anthelmintics include benzimidazoles such as albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxybendazole, parbendazole, and other members of this class. Additional anthelmintics include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel, or morantel. Additional anthelmintics include flucicides such as triclabendazole and clorsulon, and cestodocides such as praziquantel and epsiprantel.

The compounds of the present invention can be used in combination with derivatives and analogues of the paraherquamide/marcfortine class of anthelmintics, as well as antiparasitic oxazolines, such as those disclosed in US-5478855, US-4639771 and DE-19520936.

The compounds of the present invention can be used in combination with derivatives and analogs of the general class of dioxomorpholine antiparasitics described in WO-9615121, as well as with anthelmintic active cyclic depsipeptides such as those described in WO9611945, WO-9319053, WO-9325543, EP-626375, EP-382173, WO-9419334, EP-382173 and EP-503538.

The compounds of the present invention can be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphorus compounds; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide and the like; neonicotinoids such as imidacloprid and the like.

The compounds of the present invention can be used in combination with terpene alkaloids described, for example, in WO 95/19363 or WO 04/72086, in particular the compounds disclosed in these documents.

Other examples of such biologically active compounds with which the compounds of the present invention can be used in combination include, but are not limited to, the following.

Organophosphorus compounds: acephate, azametifos, azinphos-ethyl, azinphos-methyl, bromphos, bromphos-ethyl, cadusafos, chlorethoxyphos, chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demetonS-methyl, demeton^-methylsulfone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, ethoprofos, etrimphos, famfour, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazophos, fonofos, formotion, fosthiazate, heptenophos, isazophos, isothioate, isoxathion, malathion, metacryphos, methamidophos, methidathion, methyl parathion, os, monocrotophos, naled, omethoate, oxydemetonmethyl, paraoxon, parathion, parathion-methyl, phentoate, fosalone, phospholane, phosphocarb, phosmet, phosphamidon, phorate, phoxim, pirimiphos, pirimiphos-methyl, profenofos, propafos, proetamphos, prothiophos, pyraclofos, pyridapention, quinalphos, sulprofos, temefos, terbufos, tebupirimphos, tetrachlorvinphos, timeton, tiazofos, trichlorfon, vamidothion.

Carbamates: alanicarb, aldicarb, 2-sec-butylphenylmethylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloetocarb, etiophencarb, fenoxycarb, fentiocarb, furatiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, ilbutyril( methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiophanox, triazamate, UC-51717.

Pyrethroids: acrinatine, allethrin, alphamethrin, 5-benzyl-3-furylmethyl-(E)-(^)-cis-2,2-dimethyl3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bifenthrin, beta-cyfluthrin, cyfluthrin , acypermethrin, beta-cypermethrin, bioallethrin, bioallethrin(^)-cyclopentyl isomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, cythithrin, cyphenothrin, deltamethrin, empentrin, esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenvalerate, , flumethrin , fluvalinate (D-isomer), imiprothrin, cyhalothrin, lambda-cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrins (natural products), resmethrin, tetramethrin, transfluthrin, theta-cypermethrin, silafluofen, tau-fluvalinate, tefluthrin, tralomethrin, zeta- cypermethrin.

Arthropod growth regulators: a) inhibitors of chitin synthesis: benzoylurea compounds: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezin, diophenolan, hexythiazox, etoxazole, chlorine

- 14 047112 phentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) juvenoids: pyriproxyfen, methoprene (including S-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen.

Other antiparasitics: acequinocyl, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus thuringiensis, bensultap, biphenazate, binapacryl, bromopropylate, BTG-504, BTG-505, camphechlor, cartap, chlorobenzilate, chlordimeform, chlorfenapyr, chromaphenozide, clothianidin , cyromazine, diacloden, diafenthiuron, DBI-3204, dynactin, dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan, ethiprole, etofenprox, phenazaquin, flumite, MTI-800, fenpiroximate, fluacripyrim, flubenzimine, flubrocitrinate, flufenzine, flufenprox, hair dryer, halofenprox, hydramethylnon , IKI-220, kanemite, NC-196, neem guard, nidinorterfuran, nitenpyram, SD-35651, WL-108477, pyridaril, propargite, protrifenbut, pymetrozine, pyridaben, pyrimidifene, NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, silafluofen, silomadin, spinosad, tebufenpyrad, tetradiphone, tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad, triazamate, triethoxyspinosin, trinactin, verbutin, vertalek, YI-5301.

Biological agents: delta-endotoxin Bacillus thuringiensis ssp. aizawai, kurstaki, Bacillus thuringiensis, baculovirus, entomopathogenic bacteria, viruses and fungi.

Bactericides: chlortetracycline, oxytetracycline, streptomycin. Other biological agents: enrofloxacin, febantel, penetamate, moloxicam, cephalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinom, florfenicol, buserelin, cefovecin, tulathromycin, ceftiofur, carprofen, metaflumizone, rantel, triclabendazole.

Another aspect of the present invention relates to the use of a compound of formula (I) or a preferred individual compound as defined above, a composition containing at least one compound of formula (I) or at least one preferred individual compound as defined above, or a fungicidal or insecticidal mixture, containing at least one compound of formula (I) or at least one preferred single compound as defined above, in mixture with other fungicides or insecticides described above, for the control or prevention of infestation of plants, for example beneficial plants such as crops, material for their propagation, for example seeds, harvested crops, for example harvested food crops, or non-living materials by insects or plant pathogens, preferably fungal organisms.

A further aspect of the present invention relates to a method for controlling or preventing the infestation of plants, e.g. beneficial plants such as crops, their propagation material, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living materials by insects, or phytopathogenic or spoilage microorganisms, or organisms potentially harmful to humans, especially fungal organisms, which involves the use of a compound of formula (I) or a preferred individual compound as defined above as an active ingredient in relation to plants, parts of plants or their place of growth, in relation to the material for their reproduction or in relation to any part of non-living materials.

Control or prevention means reducing the degree of infestation by insects, or phytopathogenic or spoilage microorganisms, or organisms potentially harmful to humans, especially fungal organisms, to such a level that improvement is visible.

A preferred method of controlling or preventing infection of crops by phytopathogenic microorganisms, especially fungal or insect organisms, which involves the use of a compound of formula (I) or an agrochemical composition containing at least one of these compounds is foliar application. The frequency of application and rate of application will depend on the risk of infection by the relevant pathogen or insect. However, the compounds of formula (I) can also enter the plant from the soil through the roots (systemic action) by irrigating the plant site with a liquid formulation or by applying the compounds in solid form to the soil, for example in granular form (soil application). . In the case of water rice crops, such granules can be applied to a flooded rice field. The compounds of formula (I) can also be applied to seeds (coating) by impregnating the seeds or tubers with either a liquid fungicide composition or by coating them with a solid composition.

A composition, for example a composition containing a compound of formula (I) and, if necessary, solid or liquid excipients or monomers for encapsulating the compound of formula (I), can be prepared in a known manner, typically by thoroughly mixing and/or grinding the compound with excipients, for example solvents, solid carriers and optionally surfactants (surfactants).

Preferred application rates are usually from 5 g to 2 kg of active ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kg a. i./ha, most preferably from 20 g to 600 g a.

- 15 047112

i./ha. When used as a seed drench, suitable dosages range from 10 mg to 1 g of active substance per 1 kg of seeds.

When the combinations of the present invention are used to treat seeds, rates of 0.001 to 50 g of the compound of formula (I) per kg of seed, preferably 0.01 to 10 g per kg of seed, are generally sufficient.

Preference is given to the following mixtures of the compounds of formula (I) with the active ingredients. The abbreviation TX means one compound selected from the group of compounds from 1.a.01 - 1.a.32 to 1.z.01 - 1.Z.32, described in table. 1, and the compounds described in table. 2 (below):

excipient selected from the group of substances consisting of petroleum oils (alternative name) (628)+TC, acaricide selected from the group of substances consisting of 1,1-bis-(4-chlorophenyl)-2-ethoxyethanol (IUPAC name ) (910)+TX, 2,4-dichlorophenylbenzenesulfonate (IUPAC name) (1059)+TX, 2-fluoro-N-methyl-N-1-naphtylacetamide (IUPAC name) (1295)+TX , 4-chlorophenylphenylsulfone (IUPAC name) (981)+TX, abamectin (1)+TX, acequinocyl (3)+TX, acetoprol [CCN]+TX, acrinatrine (9)+TX, aldicarb (16)+TX, aldoxycarb (863)+TX, alpha-cypermethrin (202)+TX, amidithione (870)+TX, amidoflumet [CCN]+TX, amidothioate (872)+TX, amitone (875)+TX, amitone hydrooxalate (875)+ TX, amitraz (24)+TX, aramite (881)+TX, arsenic oxide (882)+TX, AVI 382 (compound code)+TX, AZ 60541 (compound code)+TX, azinphos-ethyl (44)+TX , azinphos-methyl (45)+TX, azobenzene (IUPAC name) (888)+TX, azocyclotine (46)+TX, azotoate (889)+TX, benomyl (62)+TX, benoxaphos (alternative name) [CCN ]+TX, benzoximate (71)+TX, benzyl benzoate (IUPAC name) [CCN]+TX, biphenazate (74)+TX, bifenthrin (76)+TX, binapacryl (907)+TX, brofenvalerate (alternative name)+ TC, bromocyclene (918)+TC, bromophos (920)+TC, bromophos-ethyl (921)+TC, bromopropylate (94)+TC, buprofezin (99)+TC, butocarboxim (103)+TC, butoxycarboxim (104) +TC, butylpyridabene (alternative name)+TC, calcium polysulfide (IUPAC name) (111)+TC, camphechlor (941)+TC, carbanolate (943)+TC, carbaryl (115)+TC, carbofuran (118)+ TC, carbophenothione (947)+TC, CGA 50'439 (development code) (125)+TC, quinomethionate (126)+TC, chlorobenzide (959)+TC, chlordimeform (964)+TC, chlordimeform hydrochloride (964)+ TC, chlorfenapyr (130)+TC, chlorphenetol (968)+TC, chlorphenson (970)+TC, chlorphensulfide (971)+TC, chlorfenvinphos (131)+TC, chlorobenzilate (975)+TC, chloromebuform (977)+TC , chloromethiuron (978)+TC, chlorpropylate (983)+TC, chlorpyrifos (145)+TC, chlorpyrifos-methyl (146)+TC, chlorothiophos (994)+TC, cinerin I (696)+TC, cinerin II (696 )+TX, cinerins (696)+TX, clofentesine (158)+TX, closantel (alternative name) [CCN]+TX, coumaphos (174)+TX, crotamiton (alternative name) [CCN]+TX, crotoxiphos (1010 )+TC, kufraneba (1013)+TC, cyanoate (1020)+TC, cyflumetofen (CAS registration no.: 400882-07-7)+TC, cyhalothrin (196)+TC, cyhexatin (199)+TC, cypermethrin ( 201)+TX, DCPM (1032)+TX, DDT (219)+TX, demefion (1037)+TX, demefion-0 (1037)+TX, demefion-S (1037)+TX, demeton (1038)+TX , demeton-methyl (224) + TX, demeton-O (1038) + TX, demetonO-methyl (224) + TX, demetona-S (1038) + TX, demeton^-methyl (224) + TX, demeton^- methylsulfone (1039) + TX, diafenthiuron (226) + TX, dialifos (1042) + TX, diazinon (227) + TX, dichlorfluanide (230) + TX, dichlorvos (236) + TX, diclifos (alternative name) + TX, dicofol (242)+TX, dicrotophos (243)+TX, dienochlor (1071)+TX, dimefox (1081)+TX, dimethoate (262)+TX, dynactin (alternative name) (653)+TX, dinex (1089) +TX, dinex-diclexin (1089)+TX, dinobuton (269)+TX, dinocap (270)+TX, dinocap-4 [CCN]+TX, dinocap-6 [CCN]+TX, dinocton (1090)+TX , dinopentone (1092)+TX, dinosulfone (1097)+TX, dinoterbone (1098)+TX, dioxathione (1102)+TX, diphenylsulfone (IUPAC name) (1103)+TX, disulfiram (alternate name) [CCN]+ TX, disulfoton (278)+TX, DNOC (282)+TX, dophenapine (1113)+TX, doramectin (alternative name) [CCN]+TX, endosulfan (294)+TX, endothione (1121)+TX, EPN ( 297)+TX, eprinomectin (alternative name) [CCN]+TX, ethion (309)+TX, methyl ethoate (1134)+TX, etoxazole (320)+TX, etrimphos (1142)+TX, phenazaflor (1147) +TX, phenazaquin (328)+TX, fenbutatin oxide (330)+TX, phenothiocarb (337)+TX, fenpropathrin (342)+TX, fenpyrad (alternative name)+TX, fenpyroximate (345)+TX, fenzone (1157 )+TX, fentrifanil (1161)+TX, fenvalerate (349)+TX, fipronil (354)+TX, fluacripyrim (360)+TX, fluazuron (1166)+TX, flubenzimine (1167)+TX, flucycloxuron (366) +TX, flucitrinate (367)+TX, fluenethyl (1169)+TX, flufenoxuron (370)+TX, flumethrin (372)+TX, fluorbenzide (1174)+TX, fluvalinate (1184)+TX, FMC 1137 (development code ) (1185)+TX, formethanate (405)+TX, formatenate hydrochloride (405)+TX, formothione (1192)+TX, formparanate (1193)+TX, gamma-NSN (430)+TX, gliodin (1205)+ TX, galfenprox (424)+TX, heptenophos (432)+TX, hexadecylcyclopropanecarboxylate (IUPAC name) (1216)+TX, hexythiazox (441)+TX, iodomethane (IUPAC name) (542)+TX , isocarbophos (alternative name) (473)+TX, isopropyl-O-(methoxyaminothiophosphoryl) salicylate (IUPAC name) (473)+TX, ivermectin (alternative name) [CCN]+TX, jasmoline I (696)+TX, jasmoline II (696) + TX, iodofenphos (1248) + TX, lindane (430) + TX, lufenuron (490) + TX, malathion (492) + TX, malonoben (1254) + TX, mecarbam (502) + TX, mephospholane (1261)+TX, mesulfene

- 16 047112 (alternative name) [CCN]+TX, metacryphos (1266)+TX, methamidophos (527)+TX, methidathione (529)+TX, methiocarb (530)+TX, methomyl (531)+TX, methyl bromide ( 537)+TX, metolcarb (550)+TX, mevinphos (556)+TX, mexacarbate (1290)+TX, milbemectin (557)+TX, milbemycin oxime (alternative name) [CCN]+TX, mipafox (1293)+ TX, monocrotophos (561)+TX, morphothione (1300)+TX, moxidectin (alternative name) [CCN]+TX, naleda (567)+TX, NC-184 (compound code)+TX, NC-512 (compound code )+TX, nifluridide (1309)+TX, nikkomycins (alternative name) [CCN]+TX, nitrilecarb (1313)+TX, nitrilecarb-zinc chloride complex 1:1 (1313)+TX, NNI-0101 (compound code) +TX, NNI-0250 (compound code)+TX, omethoate (594)+TX, oxamyl (602)+TX, eprophos oxide (1324)+TX, oxydisulfoton (1325)+TX, pp'-DDT (219)+ TX, parathion (615)+TX, permethrin (626)+TX, petroleum oils (alternative name) (628)+TX, phencapton (1330)+TX, phentoate (631)+TX, phorate (636)+TX, fosalone (637)+TC, phospholane (1338)+TC, phosmet (638)+TC, phosphamidone (639)+TC, phoxim (642)+TC, pirimiphos-methyl (652)+TC, polychloroterpenes (traditional name) (1347 ) + TX, polynactins (alternative name) (653) + TX, proclonol (1350) + TX, profenofos (662) + TX, promacil (1354) + TX, propargite (671) + TX, propetamphos (673) + TX, propoxur (678) + TX, protidation (1360) + TX, protoate (1362) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridabene (699) + TX , pyridafenthione (701)+TX, pyrimidifene (706)+TX, pyrimitate (1370)+TX, quinalphos (711)+TX, quinthiophos (1381)+TX, R-1492 (development code) (1382)+TX, RA -17 (development code) (1383)+TX, rotenone (722)+TX, shradan (1389)+TX, sebuphos (alternative name)+TX, selamectin (alternative name) [CCN]+TX, SI-0009 (code compounds)+TX, sofamide (1402)+TX, spirodiclofen (738)+TX, spiromesifene (739)+TX, SSI-121 (development code) (1404)+TX, sulfiram (alternative name) [CCN]+TX, sulfluramide (750)+TX, sulfotepa (753)+TX, sulfur (754)+TX, SZI-121 (development code) (757)+TX, tau-fluvalinate (398)+TX, tebufenpyrad (763)+TX, TERR (1417)+TX, terbama (alternative name)+TX, tetrachlorvinphos (777)+TX, tetradiphon (786)+TX, tetranactin (alternative name) (653)+TX, tetrasula (1425)+TX, thiafenox (alternative name)+TX, thiocarboxime (1431)+TX, thiophanox (800)+TX, thiometon (801)+TX, thioquinox (1436)+TX, thuringiensin (alternative name) [CCN]+TX, triamiphos (1441)+TX , triaratene (1443)+TX, triazophos (820)+TX, triazuron (alternative name)+TX, trichlorfon (824)+TX, triphenofos (1455)+TX, trinactin (alternative name) (653)+TX, vamidothione ( 847)+TX, vaniliprole [CCN] and YI-5302 (compound code)+TX, an algaecide selected from the group of substances consisting of betoxazine [CCN]+TX, copper dioctanoate (IUPAC name) (170)+TX, sulfate copper (172)+TX, cibutrin [CCN]+TX, dichlon (1052)+TX, dichlorophen (232)+TX, endothal (295)+TX, fentin (347)+TX, slaked lime [CCN]+TX, nabam (566)+TX, quinoclamine (714)+TX, quinonamide (1379)+TX, simazine (730)+TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347)+ TX, anthelmintic selected from the group of substances consisting of abamectin (1)+TX, crufomate (1011)+TX, doramectin (alternative name) [CCN]+TX, emamectin (291)+TX, emamectin benzoate (291)+ TX, eprinomectin (alternative name) [CCN]+TX, ivermectin (alternative name) [CCN]+TX, milbemycin oxime (alternative name) [CCN]+TX, moxidectin (alternative name) [CCN]+TX, piperazine [CCN ]+TX, selamectin (alternative name) [CCN]+TX, spinosad (737) and thiophanate (1435)+TX, an avicid selected from the group of substances consisting of chloralose (127)+TX, endrin (1122)+TX, fenthion (346)+TX, pyridin-4-amine (IUPAC name) (23) and strychnine (745)+TX, a bactericide selected from the group of substances consisting of 1-hydroxy-1H-pyridine-2-thione (name according to IUPAC) (1222)+TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (name according to IUPAC) (748)+TX, 8-hydroxyquinoline sulfate (446)+TX, bronopol (97)+TX, copper dioctanoate ( name according to IUPAC) (170)+TX, copper hydroxide (name according to IUPAC) (169)+TX, cresol [CCN]+TX, dichlorophen (232)+TX, dipyrithione (1105)+TX, dodicine (1112)+TX , fenaminosulfate (1144)+TX, formaldehyde (404)+TX, hydrarhafen (alternative name) [CCN]+TX, kasugamycin (483)+TX, kasugamycin hydrochloride hydrate (483)+TX, nickel bis-(dimethyldithiocarbamate) (name according to IUPAC) (1308)+TX, nitrapyrine (580)+TX, octylinone (590)+TX, oxolinic acid (606)+TX, oxytetracycline (611)+TX, potassium hydroxyquinoline sulfate (446)+TX, probenazole (658 )+TX, streptomycin (744)+TX, streptomycin sesquisulfate (744)+TX, teclophthalam (766)+TX and thiomersal (alternative name) [CCN]+TX, biological agent selected from the group of substances consisting of Adoxophyes orana GV (alternative name) (12)+TX, Agrobacterium radiobacter (alternative name) (13)+TX, Amblyseius spp. (alternative name) (19)+TX, Anagrapha falcifera NPV (alternative name) (28)+TX, Anagrus atomus (alternative name) (29)+TX, Aphelinus abdominalis (alternative name) (33)+TX, Aphidius colemani ( alternative name) (34)+TX, Aphidoletes aphidimyza (alternative name) (35)+TX, Autographa californica NPV (alternative name) (38)+TX, Bacillus firmus (alternative name) (48)+TX, Bacillus sphaericus Neide ( scientific name) (49)+TX, Bacillus thuringiensis Berliner (scientific name) (51)+TX, Bacillus thuringiensis subsp. aizawai (scientific name)

- 17 047112 (51)+TX, Bacillus thuringiensis subsp. israelensis (scientific name) (51)+TX, Bacillus thuringiensis subsp. japonensis (scientific name) (51)+TX, Bacillus thuringiensis subsp. kurstaki (scientific name) (51)+TX, Bacillus thuringiensis subsp. tenebrionis (scientific name) (51)+TX, Beauveria bassiana (alternative name) (53)+TX, Beauveria brongniartii (alternative name) (54)+TX, Chrysoperla carnea (alternative name) (151)+TX, Cryptolaemus montrouzieri ( alternative name) (178)+TX, Cydia pomonella GV (alternative name) (191)+TX, Dacnusa sibirica (alternative name) (212)+TX, Diglyphus isaea (alternative name) (254)+TX, Encarsia formosa (scientific name) (293)+TX, Eretmocerus eremicus (alternative name) (300)+TX, Helicoverpa zea NPV (alternative name) (431)+TX, Heterorhabditis bacteriophora and H. megidis (alternative name) (433)+TX, Hippodamia convergens (alternative name) (442)+TX, Leptomastix dactylopii (alternative name) (488)+TX, Macrolophus caliginosus (alternative name) (491)+TX, Mamestra brassicae NPV (alternative name) (494)+TX, Metaphycus helvolus (alternative name) (522)+TX, Metarhizium anisopliae var. acridum (scientific name) (523)+TX, Metarhizium anisopliae var. anisopliae (scientific name) (523)+TX, Neodiprion sertifer NPV and N. lecontei NPV (alternative name) (575)+TX, Orius spp. (alternative name) (596)+TX, Paecilomyces fumosoroseus (alternative name) (613)+TX, Phytoseiulus persimilis (alternative name) (644)+TX, Spodoptera exigua multicapsid nuclear polyhedrosis virus (scientific name) (741)+TX, Steinernema bibionis (alternative name) (742)+TX, Steinernema carpocapsae (alternative name) (742)+TX, Steinernema feltiae (alternative name) (742)+TX, Steinernema glaseri (alternative name) (742)+TX, Steinernema riobrave (alternative name) (742)+TX, Steinernema riobravis (alternative name) (742)+TX, Steinernema scapterisci (alternative name) (742)+TX, Steinernema spp. (alternative name) (742)+TX, Trichogramma spp. (alternative name) (826)+TX, Typhlodromus occidentalis (alternative name) (844) and Verticillium lecanii (alternative name) (848)+TX, bacillus subtilis var. amyloliquefaciens, strain FZB24 (available from Novozymes Biologicals Inc., 5400 Corporate Circle, Salem, VA 24153, USA, and known under the trade name Taegro®) + TX, a soil sterilizer selected from the group of substances consisting of iodomethane (IUPAC name) (542) and methyl bromide (537) + TX, a chemosterilant selected from the group of substances consisting of afolate [CCN] + TX, bisazir (alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, diflubenzuron (250)+TX, dimatipha (alternative name) [CCN]+TX, hemel [CCN]+TX, hemp [CCN]+TX, metep [CCN]+TX, methiotepa [CCN]+TX, methylafolate [CCN]+ TX, morzide [CCN]+TX, penfluron (alternate name) [CCN]+TX, tepa [CCN]+TX, thiochempa (alternate name) [CCN]+TX, thiotepa (alternate name) [CCN]+TX, tretamine (alternative name) [CCN] and uredeps (alternative name) [CCN]+TX, 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 (IUPAC name) (222)+TX, (E)-tridec-4-en-1-yl acetate (IUPAC name) (829)+TX, (E)-6-methylhept- 2-en-4-ol (IUPAC name) (541)+TX, (E,Z)tetradeca-4,10-dien-1-ylacetate (IUPAC name) (779)+TX, ^)-dodec- 7-en-1-yl acetate (IUPAC name) (285)+TX, ^)-hexadec-11-enal (IUPAC name) (436)+TX, (Z)hexadec-11-en-1-yl acetate ( IUPAC name) (437)+TX, ^)-hexadec-13-en-11-yn-1-yl acetate (IUPAC name) (438)+TX, ^)-icose-13-en-10-one ( IUPAC name) (448)+TX, (Z)tetradec-7-en-1-ala (IUPAC name) (782)+TX, ^)-tetradec-9-en-1-ol (IUPAC name) (783)+TX, ^)-tetradec-9-en-1-ylacetate (IUPAC name) (784)+TX, (7E^)-dodeca7,9-dien-1-ylacetate (IUPAC name) (283 )+TX, (92.11E)-tetradeca-9,11-dien-1-ylacetate (IUPAC name) (780)+TX, (92.12E)-tetradeca-9,12-dien-1-ylacetate ( IUPAC name) (781)+TX, 14-methyloctadec-1-ene (IUPAC name) (545)+TX, 4-methylnonan-5-ol with 4methylnonan-5-one (IUPAC name) (544)+ TX, alpha-multistriatin (alternative name) [CCN]+TX, brevicomin (alternative name) [CCN]+TX, codeleur (alternative name) [CCN]+TX, codlemon (alternative name) (167)+TX, quelura ( alternative name) (179)+TX, disparlura (277)+TX, dodec-8-en-1-yl acetate (IUPAC name) (286)+TX, dodec-9ene-1-yl acetate (IUPAC name) (287 )+TX, dodeci-8+TX, 10-dien-1-yl acetate (IUPAC name) (284)+TX, dominicalur (alternative name) [CCN]+TX, ethyl 4-methyloctanoate (IUPAC name) ( 317)+TX, eugenol (alternative name) [CCN]+TX, frontalina (alternative name) [CCN]+TX, gossyplura (alternative name) (420)+TX, grandlura (421)+TX, grandlura I (alternative name ) (421)+TX, grandlura II (alternative name) (421)+TX, grandlura III (alternative name) (421)+TX, grandlura IV (alternative name) (421)+TX, hexalura [CCN]+TX, ipsdienol (alternative name) [CCN]+TX, ipsenol (alternative name) [CCN]+TX, japonilur (alternative name) (481)+TX, lineatin (alternative name) [CCN]+TX, litlura (alternative name) [ CCN]+TX, luplura (alternative name) [CCN]+TX, medlura [CCN]+TX, megatomoic acid (alternative name) [CCN]+TX, methyleugenol (alternative name) (540)+TX, muscalura (563) +TX, octadeca-2,13-dien-1-ylacetate (IUPAC name) (588)+TX, octadeca-3,13-dien-1-ylacetate (IUPAC name)

- 18 047112 (589)+TX, orphralur (alternative name) [CCN]+TX, oryctalur (alternative name) (317)+TX, ostramon (alternative name) [CCN]+TX, siglur [CCN]+TX, sordidina A (alternative name) (839)+TX, trimedlura B1 (alternative name) (839)+TX, trimedlura B2 (alternative name) (839)+TX, trimedlura C (alternative name) (839) and Trank-Cola (alternative name ) [CCN]+TX, an insect repellent selected from the group of substances consisting of 2-(octylthio)ethanol (IUPAC name) (591)+TX, butopyronoxyl (933)+TX, butoxy(polypropylene glycol) (936)+ TX, dibutyl adipate (IUPAC name) (1046)+TX, dibutyl phthalate (1047)+TX, dibutyl succinate (IUPAC name) (1048)+TX, diethyltoluamide [CCN]+TX, dimethyl carbate [CCN]+TX, dimethyl phthalate [CCN ]+TX, ethylhexanediol (1137)+TX, hexamide [CCN]+TX, methoquin-butyl (1276)+TX, methylneodecanamide [CCN]+TX, oxamate [CCN] and picaridin [CCN]+TX, an insecticide selected from group of substances consisting of 1-dichloro-1-nitroethane (IUPAC/Chemical Abstract Service name) (1058) + TX, 1,1-dichloro-2,2-bis-(4-ethylphenyl)ethane (IUPAC name) (1056)+TX, 1,2-dichloropropane (IUPAC name) (1062)+TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063)+TX, 1- bromo-2-chloroethane (IUPAC name) (916)+TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate (IUPAC name) (1451)+TX, 2 ,2-dichlorovinyl2-ethylsulfinylethylmethylphosphate (IUPAC name) (1066)+TX, 2-(1,3-dithiolan-2yl)phenyldimethylcarbamate (IUPAC/Chemical Abstract Service name) (1109)+TX, 2(2-butoxyethoxy) ethyl thiocyanate (IUPAC/Chemical Abstract Service name) (935)+TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenylmethylcarbamate (IUPAC/Chemical Abstract Service name) (1084)+TX , 2-(4-chloro-3,5-xyloxy)ethanol (IUPAC name) (986)+TX, 2-chlorovinyl diethyl phosphate (IUPAC name) (984)+TX, 2-imidazolidone (IUPAC name) (1225)+ TX, 2-isovalerylindane-1,3-dione (IUPAC name) (1246) + TX, 2-methyl(prop-2-ynyl)aminophenylmethylcarbamate (IUPAC name) (1284) + TX, 2-thiocyanatoethyl laurate (2-thiocyanatoethyl laurate IUPAC) (1433)+TX, 3-bromo-1-chloroprop-1-ene (IUPAC name) (917)+TX, 3-methyl-1-phenylpyrazol-5-yldimethylcarbamate (IUPAC name) (1283)+ TX, 4-methyl(prop-2-ynyl)amino-3,5-xylylmethylcarbamate (IUPAC name) (1285) + TX, 5,5-dimethyl-3-oxocyclohex-1-enyldimethylcarbamate (IUPAC name) (1085 )+TX, abamectin (1)+TX, acephate (2)+TX, acetamiprid (4)+TX, acethione (alternative name) [CCN]+TX, acetoprol [CCN]+TX, acrinatrine (9)+TX, acrylonitrile (IUPAC name) (861) + TX, alanicarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, aldrin (864) + TX, allethrin (17) + TX, allosamidin (alternative name) [CCN]+TX, allixicarb (866)+TX, alphacypermethrin (202)+TX, alpha-ecdysone (alternative name) [CCN]+TX, aluminum phosphide (640)+TX, amidithione (870)+TX, amidothioate (872) + TX, aminocarb (873) + TX, amitone (875) + TX, amitone hydroxalate (875) + TX, amitraz (24) + TX, anabasine (877) + TX, atidation (883) + TX, AVI 382 (compound code)+TX, AZ 60541 (compound code)+TX, azadirachtin (alternative name) (41)+TX, azametifos (42)+TX, azinphos-ethyl (44)+TX, azinphos-methyl (45 )+TX, azotoate (889)+TX, Bacillus thuringiensis deltaendotoxins (alternative name) (52)+TX, barium hexafluorosilicate (alternative name) [CCN]+TX, barium polysulfide (IUPAC/Chemical Abstract Service name) (892) +TX, bartrina [CCN]+TX, Bayer 22/190 (development code) (893)+TX, Bayer 22408 (development code) (894)+TX, bendiocarb (58)+TX, benfuracarb (60)+TX, bensultap (66) + TX, betacifluthrin (194) + TX, beta-cypermethrin (203) + TX, bifenthrin (76) + TX, bioallethrin (78) + TX, isomer of bioallethrin^-cyclopentenyl (alternative name) (79)+ TX, bioethanometrin [CCN]+TX, biopermethrin (908)+TX, bioresmethrin (80)+TX, bis-(2-chloroethyl) ether (IUPAC name) (909)+TX, bistrifluron (83)+TX, borax (86)+TX, brofenvalerate (alternative name)+TX, bromfenvinphos (914)+TX, bromocyclene (918)+TX, bromine-DDT (alternative name) [CCN]+TX, bromophos (920)+TX, bromophos -ethyl (921) + TX, bufencarb (924) + TX, buprofezin (99) + TX, butacarb (926) + TX, butathiophos (927) + TX, butocarboxim (103) + TX, butonate (932) + TX, butoxycarboxyme (104)+TX, butylpyridabene (alternative name)+TX, cadusafos (109)+TX, calcium arsenate [CCN]+TX, calcium cyanide (444)+TX, calcium polysulfide (IUPAC name) (111)+TX , camphechlor (941)+TC, carbanolate (943)+TC, carbaryl (115)+TC, carbofuran (118)+TC, carbon disulfide (name according to IUPAC/Chemical Abstract Service) (945)+TC, carbon tetrachloride (name according to IUPAC) (946)+TC, carbophenothione (947)+TC, carbosulfan (119)+TC, cartap (123)+TC, cartap hydrochloride (123)+TC, cevadin (alternative name) (725)+TC, chlorobicyclene ( 960)+TC, chlordane (128)+TC, chlordecone (963)+TC, chlordimeform (964)+TC, chlordimeform hydrochloride (964)+TC, chlorethoxyphos (129)+TC, chlorfenapyr (130)+TC, chlorfenvinphos ( 131)+TX, chlorfluazuron (132)+TX, chlormephos (136)+TX, chloroform [CCN]+TX, chloropicrin (141)+TX, chlorphoxime (989)+TX, chlorprazophos (990)+TX, chlorpyrifos (145 ) + TX, chlorpyrifos-methyl (146) + TX, chlorothiophos (994) + TX, chromafenozide (150) + TX, cinnerin I (696) + TX,

- 19 047112 cinerin II (696)+TX, cinerins (696)+TX, cis-resmethrin (alternative name)+TX, cismethrin (80)+TX, clocitrin (alternative name)+TX, cloetocarb (999)+TX, closantel (alternative name) [CCN]+TX, clothianidin (165)+TX, copper acetoarsenite [CCN]+TX, copper arsenate [CCN]+TX, copper oleate [CCN]+TX, coumaphos (174)+TX, cumitoate (1006)+TX, crotamiton (alternative name) [CCN]+TX, crotoxyphos (1010)+TX, crufomate (1011)+TX, cryolite (alternative name) (177)+TX, CS 708 (development code) (1012 )+TX, cyanophenphos (1019)+TX, cyanophos (184)+TX, cyanoate (1020)+TX, cycletrin [CCN]+TX, cycloprothrin (188)+TX, cyfluthrin (193)+TX, cyhalothrin (196) +TX, cypermethrin (201)+TX, cyphenothrin (206)+TX, cyromazine (209)+TX, cythioate (alternative name) [CCN]+TX, d-limonene (alternative name) [CCN]+TX, d- tetramethrin (alternative name) (788)+TX, DAEP (1031)+TX, dazomet (216)+TX, DDT (219)+TX, decarbofuran (1034)+TX, deltamethrin (223)+TX, demefion (1037) +TH, demefion-0 (1037)+TH, demefion-S (1037)+TH, demeton (1038)+TH, demeton-methyl (224)+TH, demeton-0 (1038)+TH, demeton-O- methyl (224) + TX, demeton-S (1038) + TX, demeton-methyl (224) + TX, demeton-methylsulfone (1039) + TX, diafenthiuron (226) + TX, dialifos (1042) + TX, diamidaphos (1044)+TX, diazinon (227)+TX, dicaptone (1050)+TX, dichlorofenthion (1051)+TX, dichlorvos (236)+TX, diclifos (alternative name)+TX, dicresyl (alternative name) [CCN ]+TX, dicrotophos (243)+TX, dicyclanil (244)+TX, dieldrin (1070)+TX, diethyl-5-methylpyrazol-3-ylphosphate (IUPAC name) (1076)+TX, diflubenzuron (250)+ TX, dilor (alternative name) [CCN]+TX, dimefluthrin [CCN]+TX, dimefox (1081)+TX, dimethane (1085)+TX, dimethoate (262)+TX, dimethrin (1083)+TX, dimethylvinphos ( 265) + TX, dimethylane (1086) + TX, dinex (1089) + TX, dinex-diclexin (1089) + TX, dinoprop (1093) + TX, dinosam (1094) + TX, dinoseb (1095) + TX, dinotefuran (271)+TC, diophenolan (1099)+TC, dioxabenzophos (1100)+TC, dioxacarb (1101)+TC, dioxathione (1102)+TC, disulfoton (278)+TC, diticrophos (1108)+TC, DNOC ( 282)+TX, doramectin (alternative name) [CCN]+TX, DSP (1115)+TX, ecdysterone (alternative name) [CCN]+TX, EI 1642 (development code) (1118)+TX, emamectin (291) +TX, emamectin benzoate (291)+TX, EMPC (1120)+TX, empentrin (292)+TX, endosulfan (294)+TX, endothion (1121)+TX, endrin (1122)+TX, ERBP (1123) +TX, EPN (297)+TX, epophenonane (1124)+TX, eprinomectin (alternative name) [CCN]+TX, esfenvalerate (302)+TX, ethos (alternative name) [CCN]+TX, etiophencarb (308) +TX, ethion (309)+TX, ethiprole (310)+TX, methyl ethoate (1134)+TX, ethoprophos (312)+TX, ethyl formate (IUPAC name) [CCN]+TX, ethyl-DDD (alternative name) (1056)+TX, ethylene dibromide (316)+TX, ethylene dichloride (chemical name) (1136)+TX, ethylene oxide [CCN]+TX, etofenprox (319)+TX, etrimphos (1142)+TX, EXD (1143 )+TC, famfura (323)+TC, fenamiphos (326)+TC, phenazaflor (1147)+TC, fenchlorvos (1148)+TC, fenetacarb (1149)+TC, fenfluthrin (1150)+TC, fenitrothion (335) +TX, fenobucarb (336)+TX, fenoxacrim (1153)+TX, fenoxycarb (340)+TX, fenpyritrin (1155)+TX, fenpropathrin (342)+TX, fenpyrad (alternative name)+TX, fensulfothione (1158) +TX, fenthion (346)+TX, fenthion-ethyl [CCN]+TX, fenvalerate (349)+TX, fipronil (354)+TX, flonicamid (358)+TX, flubendiamide (CAS Registration No.: 272451-65- 7)+TX, flucofuron (1168)+TX, flucycloxuron (366)+TX, flucitrinate (367)+TX, fluenetil (1169)+TX, flufenerim [CCN]+tX, flufenoxuron (370)+TX, flufenprox (1171 )+TX, flumethrin (372)+TX, fluvalinate (1184)+TX, FMC 1137 (development code) (1185)+TX, phonofos (1191)+TX, formatenate (405)+TX, formatenate hydrochloride (405)+ TX, formothione (1192) + TX, formparanate (1193) + TX, fosmethylane (1194) + TX, fospirat (1195) + TX, fosthiazate (408) + TX, fostiethane (1196) + TX, furatiocarb (412) + TX , furethrin (1200) + TX, gamma-cyhalothrin (197) + TX, gamma-NSN (430) + TX, guazatine (422) + TX, guazatin acetates (422) + TX, GY-81 (development code) (423 ) + TX, galfenprox (424) + TX, halofenozide (425) + TX, NCH (430) + TX, HEOD (1070) + TX, heptachlor (1211) + TX, heptenophos (432) + TX, heterophos [CCN] +TX, hexaflumuron (439)+TX, HHDN (864)+TX, hydramethylnon (443)+TX, hydrogen cyanide (444)+TX, hydroprene (445)+TX, hiquincarb (1223)+TX, imidacloprid (458) +TX, imiprotrine (460)+TX, indoxacarb (465)+TX, iodomethane (IUPAC name) (542)+TX, IPSP (1229)+TX, isazophos (1231)+TX, isobenzan (1232)+TX, isocarbophos (alternative name) (473)+TX, isodrin (1235)+TX, isofenphos (1236)+TX, isolan (1237)+TX, isoprocarb (472)+TX, isopropyl-O(methoxyaminothiophosphoryl) salicylate (IUPAC name) ) (473)+TX, isoprothiolane (474)+TX, isothioate (1244)+TX, isoxathione (480)+TX, ivermectin (alternative name) [CCN]+TX, jasmoline I (696)+TX, jasmoline II ( 696)+TX, iodofenphos (1248)+TX, juvenile hormone I (alternative name) [CCN]+TX, juvenile hormone II (alternative name) [CCN]+TX, juvenile hormone III (alternative name) [CCN]+TX , kelevana (1249)+TX, kinoprene (484)+TX, lambdacyhalothrin (198)+TX, lead arsenate [CCN]+TX, lepimectin (CCN)+TX, leptophos (1250)+TX, lindane (430)+TX , lyrimphos (1251)+TX, lufenuron (490)+TX, litidathione (1253)+TX, mcumenylmethylcarbamate (IUPAC name) (1014)+TX, magnesium phosphide (IUPAC name) (640)+TX, malathion (492 ) + TX, malonobene (1254) + TX, mazidox (1255) + TX, mecarbam (502) + TX, mecarfon (1258) + TX, menazone (1260) + TX, mephospholan (1261) + TX, mercuric chloride (513 )+TX, mesulfenphos (1263)+TX, metaflumizone (CCN)+TX, metam (519)+TX, metam-potassium (alternative name) (519)+TX, metam-sodium (519)+TX, metacryphos (1266 )+TH, methamidophos

- 20 047112 (527)+TX, methanesulfonyl fluoride (name according to IUPAC/Chemical Abstract Service) (1268)+TX, methidation (529)+TX, methiocarb (530)+TX, metocrotophos (1273)+TX, methomyl (531) +TC, methoprene (532)+TC, methoquin-butyl (1276)+TC, methotrine (alternative name) (533)+TC, methoxychlor (534)+TC, methoxyfenozide (535)+TC, methyl bromide (537)+TC , methyl isothiocyanate (543)+TX, methyl chloroform (alternative name) [CCN]+TX, methylene chloride [CCN]+TX, metofluthrin [CCN]+TX, metolcarb (550)+TX, methoxadiazone (1288)+TX, mevinphos (556 )+TX, mexacarbate (1290)+TX, milbemectin (557)+TX, milbemycin oxime (alternative name) [CCN]+TX, mipafox (1293)+TX, mirex (1294)+TX, monocrotophos (561)+TX , morphothione (1300)+TX, moxidectin (alternative name) [CCN]+TX, naphthalophos (alternative name) [CCN]+TX, naled (567)+TX, naphthalene (IUPAC/Chemical Abstract Service name) (1303) +TX, NC-170 (development code) (1306)+TX, NC-184 (compound code)+TX, nicotine (578)+TX, nicotine sulfate (578)+TX, nifluridide (1309)+TX, nitenpyram ( 579)+TX, nithiazine (1311)+TX, nitrilecarb (1313)+TX, complex of nitrilecarb and zinc chloride 1:1 (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250 (compound code) +TX, nornicotine (traditional name) (1319)+TX, novaluron (585)+TX, noviflumuron (586)+TX, O-5-dichloro-4-iodophenyl-O-ethylethylphosphonothioate (IUPAC name) (1057)+ TX, O,O-diethyl-O-4-methyl-2-oxo-2H-chromen-7-ylphosphorothioate (IUPAC name) (1074) + TX, O,O-diethyl-O-6-methyl-2- propylpyrimidin-4-ylphosphorothioate (IUPAC name) (1075)+TX, O,O,O',O'-tetrapropyldithiopyrophosphate (IUPAC name) (1424)+TX, oleic acid (IUPAC name) (593)+TX , omethoate (594) + TX, oxamyl (602) + TX, oxydemeton-methyl (609) + TX, oxydeprophos (1324) + TX, oxydisulfoton (1325) + TX, pp'DDT (219) + TX, para-dichlorobenzene [CCN]+TX, parathion (615)+TX, parathion-methyl (616)+TX, penfluron (alternate name) [CCN]+TX, pentachlorophenol (623)+TX, pentachlorophenyl laurate (IUPAC name) (623)+ TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, RN 60-38 (development code) (1328) + TX, phencapton (1330) + TX, phenothrin (630) + TX, phentoate (631)+TX, phorate (636)+TX, fosalone (637)+TX, phospholane (1338)+TX, phosmet (638)+TX, phosnichlor (1339)+TX, phosphamidone (639)+TX, phosphine ( name according to IUPAC) (640) + TX, phoxima (642) + TX, phoxim-methyl (1340) + TX, pirimetaphos (1344) + TX, pirimicarb (651) + TX, pirimiphos-ethyl (1345) + TX, pirimiphos -methyl (652)+TX, polychlorodicyclopentadnene isomers (IUPAC name) (1346)+TX, polychloroterpenes (traditional name) (1347)+TX, potassium arsenite [CCN]+TX, potassium thiocyanate [CCN]+TX, prallethrin ( 655)+TX, precocene I (alternative name) [CCN]+TX, precocene II (alternative name) [CCN]+TX, precocene III (alternative name) [CCN]+TX, primidophos (1349)+TX, profenofos ( 662)+TX, profluthrin [CCN]+TX, promacil (1354)+TX, promecarb (1355)+TX, propaphos (1356)+TX, propetamphos (673)+TX, propoxur (678)+TX, protidation (1360 )+TX, prothiophos (686)+TX, protoate (1362)+TX, protrifenbut [CCN]+TX, pymetrozine (688)+TX, pyraclophos (689)+TX, pyrazophos (693)+TX, pyresmethrin (1367) +TX, pyrethrin I (696)+TX, pyrethrin II (696)+TX, pyrethrins (696)+TX, pyridabene (699)+TX, pyridalyl (700)+TX, pyridafenthione (701)+TX, pyrimidifene (706 )+TX, pyrimitate (1370)+TX, pyriproxyfen (708)+TX, quassia (alternative name) [CCN]+TX, quinalphos (711)+TX, quinalphos-methyl (1376)+TX, quinothione (1380)+ TX, quintiophos (1381)+TX, R-1492 (development code) (1382)+TX, rafoxanide (alternative name) [CCN]+TX, resmethrin (719)+TX, rotenone (722)+TX, RU 15525 ( development code) (723)+ТХ, RU 25475 (development code) (1386)+ТХ, ryanium (alternative name) (1387)+ТХ, ryanodine (traditional name) (1387)+ТХ, sabadilla (alternative name) (725 )+TX, shradana (1389)+TX, sebuphos (alternative name)+TX, selamectin (alternative name) [CCN]+TX, SI-0009 (compound code)+TX, SI-0205 (compound code)+TX, SI-0404 (compound code)+TX, SI-0405 (compound code)+TX, silafluofen (728)+TX, SN 72129 (development code) (1397)+TX, sodium arsenite [CCN]+TX, sodium cyanide ( 444)+TX, sodium fluoride (IUPAC/Chemical Abstract Service name) (1399)+TX, sodium hexafluorosilicate (1400)+TX, sodium pentachlorophenoxide (623)+TX, sodium selenate (IUPAC name) (1401)+TX , sodium thiocyanate [CCN]+TX, sofamide (1402)+TX, spinosad (737)+TX, spiromesifen (739)+TX, spirotetramate (cCn)+TX, sulcofuron (746)+TX, sulcofuron-sodium (746) +TC, sulfluramide (750)+TC, sulfotepa (753)+TC, sulfuryl fluoride (756)+TC, sulprophos (1408)+TC, tar oils (alternative name) (758)+TC, taufluvalinate (398)+TC, tazimcarb (1412)+TX, TDE (1414)+TX, tebufenozide (762)+TX, tebufenpyrad (763)+TX, tebupirimphos (764)+TX, teflubenzuron (768)+TX, tefluthrin (769)+TX, temephos (770)+TX, TERP (1417)+TX, terallethrin (1418)+TX, terbam (alternative name)+TX, terbufos (773)+TX, tetrachloroethane [CCN]+TX, tetrachlorvinphos (777)+TX, tetramethrin (787)+TX, tetacypermethrin (204)+TX, thiacloprid (791)+TX, thiaphenox (alternative name)+TX, thiamethoxam (792)+TX, ticrofos (1428)+TX, thiocarboxime (1431)+TX, thiocyclam (798)+TX, thiocyclam hydrooxalate (798)+TX, thiodicarb (799)+TX, thiophanox (800)+TX, thiometon (801)+TX, thionazine (1434)+TX, thiosultap (803)+TX, thiosultap -sodium (803)+TX, thuringhiensin (alternative name) [CCN]+TX, tolfenpyrad (809)+TX, tralomethrine (812)+TX, transfluthrin (813)+TX, transpermethrin (1440)+TX, triamiphos (1441 )+TX, triazamate (818)+TX, triazophos (820)+TX, triazuron (alternative name)+TX, trichlorfon (824)+TX, trichlorometaphos-3 (alternative name) [CCN]+TX,

- 21 047112 trichloronate (1452)+TX, triphenofos (1455)+TX, triflumuron (835)+TX, trimetacarb (840)+TX, triprene (1459)+TX, vamidothione (847)+TX, vaniliprole [CCN]+ TX, veratridine (alternative name) (725)+TX, veratrine (alternative name) (725)+TX, XMC (853)+TX, xylylcarb (854)+TX, YI-5302 (compound code)+TX, zeta- cypermethrin (205)+TX, zetamethrin (alternative name)+TX, zinc phosphide (640)+TX, zolaprofos (1469) and ZXI 8901 (development code) (858)+TX, cyantraniliprole [736994-63-19]+TX . -15-0]+TX, spirotetramate [203313-25-1]+TX, sulfoxaflor [946578-00-3]+TX, flufiprol [704886-18-0]+TX, meperfluthrin [915288-13-0]+ TX, tetramethylfluthrin [84937-88-2] + TX, triflumesopyrim (disclosed in WO 2012/092115) + TX, a molluscicide selected from the group of substances consisting of bis-(tributyltin) oxide (IUPAC name) (913) + TX , bromoacetamide [CCN]+TX, calcium arsenate [CCN]+TX, cloetocarb (999)+TX, copper acetoarsenite [CcN]+TX, copper sulfate (172)+TX, fentin (347)+TX, ferric phosphate (name according to IUPAC) (352) + TX, metaldehyde (518) + TX, methiocarb (530) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX, pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623 )+TC, tazimcarb (1412)+TC, thiodicarb (799)+TC, tributyltin oxide (913)+TC, triphenmorph (1454)+TC, trimetacarb (840)+TC, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347)+TX, pyriprole [394730-71-3]+TX, nematicide selected from the group of substances consisting of AKD-3088 (compound code)+TX, 1,2dibromo-3- chloropropane (IUPAC/Chemical Abstract Service name) (1045)+TX, 1,2dichloropropane (IUPAC/Chemical Abstract Service name) (1062)+TX, 1,2dichloropropane with 1,3-dichloropropene (IUPAC name) ( 1063)+TX, 1,3-dichloropropene (233)+TX, 3,4-dichlorotetrahydrothiophene-1,1-dioxide (IUPAC/Chemical Abstract Service name) (1065)+TX, 3-(4-chlorophenyl)- 5-methylrhodanine (IUPAC name) (980)+TX, 5methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid (IUPAC name) (1286)+TX, 6isopentenylaminopurine (alternative name) (210 )+TX, abamectin (1)+TX, acetoprol [CCN]+TX, alanicarb (15)+TX, aldicarb (16)+TX, aldoxycarb (863)+TX, AZ 60541 (compound code)+TX, benclotiase [ CCN]+TX, benomyl (62)+TX, butylpyridabene (alternative name)+TX, cadusafos (109)+TX, carbofuran (118)+TX, carbon disulfide (945)+TX, carbosulfan (119)+TX, chloropicrin ( 141)+TX, chlorpyrifos (145)+TX, cloetocarb (999)+TX, cytokinins (alternative name) (210)+TX, dazomet (216)+TX, DBCP (1045)+TX, DCIP (218)+TX , diamidaphos (1044)+TX, dichlorofenthione (1051)+TX, diclifos (alternative name)+TX, dimethoate (262)+TX, doramectin (alternative name) [CCN]+TX, emamectin (291)+TX, emamectin benzoate (291)+TX, eprinomectin (alternative name) [CCN]+TX, ethoprophos (312)+TX, ethylene dibromide (316)+TX, fenamiphos (326)+TX, fenpyrad (alternative name)+TX, fensulfothione (1158) +TX, fosthiazate (408)+TX, fostiethane (1196)+TX, furfural (alternative name) [CCN]+TX, GY-81 (development code) (423)+TX, heterophos [CCN]+TX, iodomethane ( IUPAC name) (542)+TX, isamidophos (1230)+TX, isazophos (1231)+TX, ivermectin (alternative name) [CCN]+TX, kinetin (alternative name) (210)+TX, mecarfon (1258) +TC, metam (519)+TC, metam-potassium (alternative name) (519)+TC, metam-sodium (519)+TC, methyl bromide (537)+TC, methyl isothiocyanate (543)+TC, milbemycin oxime (alternative name) [CCN]+TX, moxidectin (alternative name) [CCN]+TX, compositions based on Myrothecium verrucaria (alternative name) (565)+TX, NC-184 (compound code)+TX, oxamyl (602)+TX , phorate (636)+TX, phosphamidone (639)+TX, phosphocarb [CCN]+TX, sebuphos (alternative name)+TX, selamectin (alternative name) [CCN]+TX, spinosad (737)+TX, terbam ( alternative name)+TX, terbufos (773)+TX, tetrachlorothiophene (IUPAC/Chemical Abstract Service name) (1422)+TX, thiaphenox (alternate name)+TX, thionazine (1434)+TX, triazophos (820)+TX , triazuron (alternative name)+TX, xylenols [CCN]+TX, YI-5302 (compound code) and zeatin (alternative name) (210)+TX, fluensulfone [318290-98-1]+TX, nitrification inhibitor, selected from a group of substances consisting of potassium ethyl xanthate [CCN] and nitrapyrin (580) + TX;

plant growth activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-methyl (6) + TX, probenazole (658) and Reynoutria sachalinensis extract (alternative name) (720) + TX, a rodenticide selected from group of substances consisting of 2-isovalerylindane-1,3-dione (IUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, alpha-chlorohydrin [ CCN]+TX, aluminum phosphide (640)+TX, antu (880)+TX, arsenic oxide (882)+TX, barium carbonate (891)+TX, bistiosemi (912)+TX, brodifacoum (89)+TX, bromadiolone (91)+TC, bromethalin (92)+TC, calcium cyanide (444)+TC, chloralose (127)+TC, chlorophacinone (140)+TC, cholecalciferol (alternative name) (850)+TC, coumachlor (1004 )+TC, coumafuryl (1005)+TC, coumatetral (175)+TC, crimidine (1009)+TC, difenacoum (246)+TC, difethialone (249)+TC, diphacinone (273)+TC, ergocalciferol (301) +TX, flocumafen (357)+TX, fluoroacetamide

- 22 047112 (379)+TX, flupropadine (1183)+TX, flupropadine hydrochloride (1183)+TX, gamma-NSN (430)+TX, NCH (430)+TX, hydrogen cyanide (444)+TX, iodomethane ( IUPAC name) (542)+TX, lindane (430)+TX, magnesium phosphide (IUPAC name) (640)+TX, methyl bromide (537)+TX, norbormide (1318)+TX, phosacetim (1336)+TX , phosphine (IUPAC name) (640)+TX, phosphorus [CCN]+TX, pindone (1341)+TX, potassium arsenite [CCN]+TX, pyrinuron (1371)+TX, scyliroside (1390)+TX, arsenite sodium [CCN]+TX, sodium cyanide (444)+TX, sodium fluoroacetate (735)+TX, strychnine (745)+TX, thallium sulfate [CCN]+TX, warfarin (851) and zinc phosphide (640)+TX , a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl piperonylate (IUPAC name) (934) + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903)+TX, farnesol with nerolidol (alternative name) (324)+TX, MB-599 (development code) (498)+TX, MGK 264 (development code) (296)+TX, piperonyl butoxide (649) + TX, piprotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesasmoline (1394) and sulfoxide (1406) + TX , an animal repellent selected from the group of substances consisting of anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, methiocarb (530) + TX, pyridin-4-amine (IUPAC name) (23) + TX, thiram (804)+TC, trimetacarb (840)+TC, zinc naphthenate [CCN] and ziram (856)+TC, a virucide selected from the group of substances consisting of imanin (alternative name) [CCN] and ribavirin (alternative name) [ CCN]+TX, a wound protectant selected from the group consisting of mercuric oxide (512)+TX, octylinone (590) and thiophanate-methyl (802)+TX, and biologically active compounds selected from the group consisting of ametokradine [86531897-4]+TX, amisulbrom [348635-87-0]+TX, azaconazole [60207-31-0]+TX, benzovindiflupyr [107295771-1]+TX, bitertanol [70585-36-3]+TX , bixafen [581809-46-3]+TX, bromuconazole [116255-482]+TX, cumoxystrobin [850881-70-8]+TX, cyproconazole [94361-06-5]+TX, difenoconazole [11944668-3]+ TX, diniconazole [83657-24-3]+TX, enoxastrobin [238410-11-2]+TX, epoxiconazole [10632508-0]+TX, fenbuconazole [114369-43-6]+TX, fenpyrazamine [473798-59- 3]+TX, fluquinconazole [136426-54-5]+TX, flusilazole [85509-19-9]+TX, flutriafol [76674-21-0]+TX, fluxapyroxade [907204-31-3]+TX, fluopyram [658066-35-4]+TX, phenaminestrobin [366815-39-6]+TX, isofetamide [875915-78-9]+TX, hexaconazole [79983-71-4]+TX, imazalil [35554-44-0 ]+TX, imibenconazole [8659892-7]+TX, ipconazole [125225-28-7]+TX, ipfentrifluconazole [1417782-08-1]+TX, isothianil [22404904-1]+TX, mandestrobin [173662-97- 0] (can be prepared in accordance with the procedures described in WO 2010/093059) + TX, mefentrifluconazole [1417782-03-6] + TX, metconazole [125116-23-6] + TX, myclobutanil [88671-89-0] +TX, paclobutrazol [76738-62-0]+TX, pefurazoate [101903-30-4]+TX, penflufen [494793-67-8]+TX, penconazole [66246-88-6]+TX, prothioconazole [178928 -70-6]+TX, pyrifenox [88283-41-4]+TX, prochlorase [67747-09-5]+TX, propiconazole [60207-90-1]+TX, simeconazole [14950890-7]+TX, tebuconazole [107534-96-3]+TX, tetraconazole [112281-77-3]+TX, triadimefon [43121-433]+TX, triadimenol [55219-65-3]+TX, triflumizole [99387-89-0] +TX, triticonazole [131983-72-7] +TX, ancymidol [12771-68-5]+TX, fenarimol [60168-88-9]+TX, nuarimol [63284-71-9]+TX, bupirimate [41483 -43-6]+TX, dimethyrimol [5221-53-4]+TX, ethirimol [23947-60-6]+TX, dodemorph [1593-777]+TX, fenpropidine [67306-00-7]+TX, fenpropimorph [67564-91-4]+TX, spiroxamine [118134-308]+TX, tridemorph [81412-43-3]+TX, cyprodinil [121552-61-2]+TX, mepanipyrim [110235-47-7] +TX, pyrimethanil [53112-28-0]+TX, fenpiclonil [74738-17-3]+TX, fludioxonil [131341-86-1]+TX, fluindapyr [1383809-87-7]+TX, benalaxyl [71626 -11-4]+TH, furalaxyl [57646-30-7]+TH, metalaxyl [57837-19-1]+TH, R-metalaxyl [70630-17-0]+TH, ofuras [58810-48-3 ]+TX, oxadixil [7773209-3]+TX, benomyl [17804-35-2]+TX, carbendazim [10605-21-7]+TX, debacarb [62732-91-6]+TX, fuberidazole [3878- 19-1]+TX, thiabendazole [148-79-8]+TX, chlozolinate [84332-86-5]+TX, dichlozoline [24201-58-9]+TX, iprodione [36734-19-7]+TX , myclozolin [54864-61-8]+TX, procymidone [32809-168]+TX, vinclozolin [50471-44-8]+TX, boscalid [188425-85-6]+TX, carboxin [5234-68-4 ]+TX, fenfuram [24691-80-3]+TX, flutolanil [66332-96-5]+TX, flutianil [958647-10-4]+TX, mepronil [55814-41-0]+TX, oxycarboxin [ 5259-88-1]+TX, penthiopyrad [183675-82-3]+TX, tifluzamide [130000-40-7]+TX, guazatin [108173-90-6]+TX, dodine [2439-10-3] [112-65-2] (free base)+TX, iminoctadine [13516-27-3]+TX, azoxystrobin [131860-33-8]+TX, dimoxystrobin [14996152-4]+TX, enestroburin {Proc. BCPC, Int. Congr., Glasgow, 2003, 1, 93}+TX, fluoxastrobin [361377-299]+TX, kresoxim-methyl [143390-89-0]+TX, methominostrobin [133408-50-1]+TX, trifloxystrobin [141517 -21-7]+TX, orysastrobin [248593-16-0]+TX, picoxystrobin [117428-22-5]+TX, pyraclostrobin [175013-18-0]+TX, pyraoxystrobin [862588-11-2]+ TX, ferbam [14484-64-1]+TX, mancozeb [8018-01-7]+TX, maneba [12427-38-2]+TX, metiram [9006-42-2]+TX, propineba [12071- 83-9]+TX, tirama [137-26-8]+TX, zineba [12122-67-7]+TX, ziram [137-30-4]+TX, captafol [2425-06-1]+TX , captan [13306-2]+TH, dichlofluanide [1085-98-9]+TH, fluorimide [41205-21-4]+TH, folpet [133-07-3]+TH, tolylfluanide [731-27-1 ]+TH, Bordeaux mixture [8011-63-0]+TH, copper hydroxide [20427-59-2]+TH, oxy- 23 047112 copper chloride [1332-40-7]+TH, copper sulfate [7758-98 -7]+TH, copper oxide [1317-39-1]+TH, mancoppers [53988-93-5]+TH, copper oxide [10380-28-6]+TH, dinocap [131-72-6] +TX, nitrotal-isopropyl [1055274-6]+TX, edifenphos [17109-49-8]+TX, iprobenphos [26087-47-8]+TX, isoprothiolane [50512-35-1]+TX, phosdifene [36519 -00-3] + TX, pyrazophos [13457-18-6] + TX, tolclofos-methyl [57018-04-9] + TX, acibenzolar^-methyl [135158-54-2] + TX, anilazine [101- 05-3]+TX, benthiavalicarb [413615-35-7]+TX, blasticidin-S [2079-00-7]+TX, quinomethionate [2439-01-2]+TX, chloroneba [2675-77-6] +TX, chlorothalonil [1897-45-6]+TX, cyflufenamide [180409-60-3]+TX, cymoxanil [57966-95-7]+TX, dichlon [11780-6]+TX, diclocymet [139920-32 -4] + TX, diclomezine [62865-36-5] + TX, dicloran [99-30-9] + TX, diethofencarb [87130-20-9] + TX, dimethomorph [110488-70-5] + TX, SYP-LI90 (flumorpha) [211867-47-9]+TX, dithianone [3347-22-6]+TX, ethaboxam [162650-77-3]+TX, etridiazole [2593-15-9]+TX, famoxadone [131807-57-3]+TX, fenamidone [161326-34-7]+TX, fenoxanil [115852-48-7]+TX, fentin [668-348]+TX, ferimzone [89269-64-7]+ TX, fluazinam [79622-59-6]+TX, fluopicolide [239110-15-7]+TX, flusulfamide [106917-52-6]+TX, fenhexamide [126833-17-8]+TX, fosetyl aluminum [ 39148-248]+TX, chemexazole [10004-44-1]+TX, iprovalicarb [140923-17-7]+TX, IKF-916 (cyazofamide) [12011688-3]+TX, kasugamycin [6980-18-3 ]+TX, metasulfocarb [66952-49-6]+TX, metrafenone [220899-036]+TX, pencycuron [66063-05-6]+TX, phthalide [27355-22-2]+TX, picarbutrazox [500207- 04-5]+TX, polyoxins [11113-80-7]+TX, probenazole [27605-76-1]+TX, propamocarb [25606-41-1]+TX, proquinazide [189278-12-4]+TX , pidiflumetofen [1228284-64-7]+TX, pyramethostrobin [915410-70-7]+TX, pyroquilone [57369-32-1]+TX, pyriophenone [688046-61-9]+TX, pyribencarb [799247-52 -2]+TX, pyrizoxazole [847749-37-5]+TX, quinoxifene [124495-18-7]+TX, quintozene [82-68-8]+TX, sulfur [7704-349]+TX, Timorex Gold ™ (plant extract containing tea tree oil, from Stockton Sgoir) + TX. tebufloquin [376645-78-2]+TX, tiadinil [223580-51-6]+TX, triazoxide [72459-586]+TX, tolprocarb [911499-62-2]+TX, trichloropyricarb [902760-40-1] +TX, tricyclazole [41814-782]+TX, triforin [26644-46-2]+TX, validamycin [37248-47-8]+TX, valifenalate [283159-90-0]+TX, zoxamide (RH7281) [ 156052-68-5]+TX, mandipropamide [374726-62-2]+TX, isopyrazam [881685-581]+TX, fenamacryl+TX, sedaxane [874967-67-6]+TX, trinexapac-ethyl [95266- 40-3]+TX, (9dichloromethylene-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl)amide 3-difluoromethyl-1-methyl-1H-pyrazole4-carboxylic acid (disclosed in WO 2007 /048556) + TX, (3',4',5'-trifluorobiphenyl-2-yl)amide 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (disclosed in WO 2006/087343) + TX, [( 3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-1,3,4,4a,5,6,6a, 12,12a, 12bdecahydro-6,12- dihydroxy-4,6a, 12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11H naphtho[2,1-b]pyrano[3,4e]pyran-4-yl]methylcyclopropanecarboxylate [915972-17 -7]+TX and 1,3,5-trimethyl-N-(2-methyl-1oxopropyl)-H-[3-(2-methylpropyl)-4-[2,2,2-trifluoro-1-methoxy- 1-(trifluoromethyl)ethyl]phenyl]-1H-pyrazole-4-carboxamide [926914-55-8]+TX, or a biologically active compound selected from the group consisting of N[(5-chloro-2isopropylphenyl)methyl] - N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide (can be prepared according to the procedures described in WO 2010/130767)+TX, 2,6-dimethyl1H,5H-[1, 4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone (can be prepared according to the procedures described in WO2011/138281) + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2c]isothiazol-3-carbonitrile+TX, 4-(2-bromo-4-fluorophenyl)-N-( 2-chloro-6-fluorophenyl)-2,5-dimethylpyrazol3-amine (can be prepared according to the procedures described in WO2012/031061)+TX, 3(difluoromethyl)-H-(7-fluoro-1,1,3 -trimethylindan-4-yl)-1-methylpyrazole-4-carboxamide (can be prepared according to the procedures described in WO 2012/084812)+TX, CAS 850881-30-0+TX, 3-(3,4-dichloro1 ,2-thiazol-5-ylmethoxy)-1,2-benzothiazol-1,1-dioxide (can be prepared according to the procedures described in WO 2007/129454)+TX, 2-[2-[(2,5- dimethylphenoxy)methyl]phenyl]-2-methoxy-Nmethylacetamide + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone (can be prepared according to the procedures described in WO 2005/070917)+TX, 2-[2-fluoro-6-[(8-fluoro-2-methyl3-quinolyl)oxy]phenyl]propan-2-ol (can be prepared according to the procedures described in WO 2011/081174)+TX, 2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluorophenyl]propan-2-ol (can be prepared according to the procedures described in WO 2011/081174)+TX, oxathiapiproline+TX [1003318-67-9], tert-butyl-N-[6-[[[(1-methyltetrazol-5-yl)phenylmethylene|amino]oxymethyl]-2-pyridyl ]carbamate+ TX, N[2-(3,4-difluorophenyl)phenyl]-3-(trifluoromethyl)pyrazine-2-carboxamide (can be prepared according to the procedures described in WO 2007/072999) + TX, 3-( difluoromethyl)-1-methylN-[(3R)-1,1,3-trimethylindan-4-yl]pyrazol-4-carboxamide (can be prepared according to the procedures described in WO 2014/013842)+TX, 2.2 ,2-trifluoroethyl-N-[2-methyl-1-[[(4-methylbenzoyl)amino]methyl]propyl]carbamate+ TX, (2RS)-2-[4-(4-chlorophenoxy)-α,α, α-trifluoro-o-tolyl]-1-(1H1,2,4-triazol-1-yl)propan-2-ol+TX, (2RS)-2-[4-(4-chlorophenoxy)-α,α ,α-trifluoro-o-tolyl]-3-methyl-1(1H-1,2,4-triazol-1-yl)butan-2-ol+TX, 2-(difluoromethyl)-N-[(3R) -3-ethyl-1,1-dimethylindan-4-yl]pyridin-3-carboxamide+TX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethylindan-4-yl]pyridin-3- carboxamide + TX, N-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylformamidine + TX, N-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5- dimethylphenyl]-N-ethyl-N-methyl-formamidine (can be prepared according to

- 24 047112 by the procedures described in WO 2007/031513)+TX, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1yl]acetyl]-4-piperidyl ]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chlorophenyl]methanesulfonate (can be prepared according to the procedures described in WO 2012/025557)+TX, 6\γ-3-ηιιη. ί-\6-[[(Ζ,')-[(Ίmethyltetrazol-5-yl)phenylmethylene]amino]oxymethyl]-2-pyridyl]carbamate (can be prepared according to the procedures described in WO 2010/000841)+TX , 2-[[3-(2-chlorophenyl)-2-(2,4difluorophenyl)oxiran-2-yl]methyl]-4H-1,2,4-triazol-3-thione (can be prepared according to the procedures described in WO 2010/146031)+TX, methyl-N[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2methylphenyl]methyl]carbamate+TX, 3-chloro-6-methyl- 5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine (can be prepared according to the procedures described in WO 2005/121104)+TX, 2-[2-chloro-4-(4chlorophenoxy)phenyl]-1 -(1,2,4-triazol-1-yl)propan-2-ol (can be prepared according to the procedures described in WO 2013/024082)+TX, 3-chloro-4-(2,6-difluorophenyl) -6-methyl-5-phenyl-pyridazine (can be prepared according to the procedures described in WO 2012/020774) + TX, 4-(2,6-difluorophenyl)-6methyl-5-phenyl-pyridazine-3-carbonitrile ( can be prepared according to the procedures described in WO 2012/020774)+TX, ^)-3-(difluoromethyl)-1-methyl-^[1,1,3-trimethylindan-4-yl]pyrazol-4carboxamide (can be prepared according to the procedures described in WO 2011/162397)+TX, 3(difluoromethyl)-N(7-fluoro-1,1,3-trimethylindan-4-yl)-1-methylpyrazole-4-carboxamide (can be prepared in according to the procedures described in WO 2012/084812)+TX, 1-[2-[[1-(4-chlorophenyl)pyrazol-3yl]oxymethyl]-3-methylphenyl]-4-methyltetrazol-5-one (can be prepared according to the procedures described in WO 2013/162072)+TX, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1yl)phenoxy]methyl ]phenyl]tetrazol-5-one (can be prepared according to the procedures described in WO 2014/051165)+TX, ^,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2 -methoxyimino-^3-dimethyl-pent3-enamide+TX, (4-phenoxyphenyl)methyl-2-amino-6-methylpyridine-3-carboxylate+TX, \-(5-\lor-2isopropylbenzyl)-Ncyclopropyl-3 -(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide [125573428-1] (can be prepared according to the procedures described in WO 2010/130767)+TX, 3Cdifluoromethyl)-\-[(I)-2 ,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl]-1-methylpyrazol-4-carboxamide [1352994-67-2]+TH, N-(2,5-dimethyl-4- phenoxyphenyl)-^ethyl-^methyl-formamidine+TX, N'-[4-(4,5dichloro-thiazol-2-yloxy)-2,5-dimethylphenyl]-N-ethyl-^methylformamidine+TX, N-( 2,5-dimethyl-4phenoxyphenyl)-Nethyl-Nmethylformamidine+TX, N-[4-(4,5-dichlorothiazol-2-yloxy)-2,5-dimethylphenyl]-Nethyl-Nmethylformamidine+TX ,

(fenpicoxamide [517875-34-2])+TX (as described in WO 2003/035617), (^)-2,2-bis-(4-fluorophenyl)1-methylethyl-^{[3-(acetyloxy)- 4-methoxy-2-pyridyl]carbonyl}^-alaninate [1961312-55-9] (florylpicoxamide - as described in WO 2016/122802)+TX, 2-(difluoromethyl)-N(1,1,3-trimethylindan- 4yl)pyridin-3-carboxamide+TX, 2-(difluoromethyl)-N(3-ethyl-1,1-dimethylindan-4-yl)pyridin-3carboxamide+TX, 2-(difluoromethyl)-\-( 1,1 -dimethyl-3-propyl-indan-4-yl)pyridin-3-carboxamide+TX, 2-(difluoromethyl)-N(3-isobutyl-1,1-dimethylindan-4-yl)pyridin-3-carboxamide+TX , 2-(difluoromethyl)N-[(3R)-1,1,3-trimethylindan-4-yl]pyridin-3-carboxamide+TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl- 1,1dimethylindan-4-yl]pyridin-3-carboxamide+TX and 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propylindan-4-yl]pyridin-3-carboxamide+TX wherein each of such carboxamide-based compounds can be prepared in accordance with the procedures described in WO 2014/095675 and/or WO 2016/139189.

References in square brackets after active ingredients, such as [3878-19-1], refer to the Chemical Abstracts Service registry number. The above-described mixing ingredients are known. If the active ingredients are included in The Pesticide Manual [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: C.D.S. TomLin; British Crop Protection Council], they are described therein under the entry number given in this document above in parentheses for the specific compound; for example, the compound abamectin is described under entry number (1). If [CCN] is added above to a particular compound in this document, then the compound in question is included in the Compendium of Pesticide Common Names, which is available on the Internet [A. Wood; Compendium of Pesticide Common Names, Copyright © 1995-2004]; for example, the compound acetoprol is described at the Internet address http://www.alanwood.net/pesticides/acetoprole.html.

Most of the above-described active ingredients are listed above under the so-called common name, the corresponding ISO common name, or other common name, which is used in individual cases. If the designation is not a common name, the essence of the designation used instead is given in parentheses for the specific compound; in this case, the name according to IUPAC is used, on

- 25 047112 IUPAC/Chemical Abstract Service title, chemical name, traditional name, compound name or development code or, if neither of these designations nor the common name is used, then an alternative name is used. CAS Registration No. means the registration number according to the Chemical Abstract Service.

In the mixture of active ingredients, compounds of formula (I) selected from compounds 1.a.01 1.a.32 to 1.z.01 - 1.Z.32, described in table. 1, and the compounds described in table. 2 (below) and the active ingredient described above are preferably present in a mixture ratio of 100:1 to 1:6000, especially 50:1 to 1:50, more particularly in a mixture ratio of 20:1 to 1: 20, even more specifically from 10:1 to 1:10, namely from 5:1 to 1:5, with particular preference being given to a ratio of 2:1 to 1:2, and a ratio of 4:1 to 2:1 is also preferred, especially in the ratio :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 . These mixture ratios are indicated by weight.

The above-described mixtures can be used in a pest control method that involves applying a composition containing the above-described mixture to pests or their habitat, excluding the method of treating the human or animal body by surgery or therapy and diagnostic methods used in practice on the human body or animal.

Mixtures containing a compound of formula (I) selected from one of the compounds from 1.a.01 - 1.a.32 to 1.z.01 - 1.Z.32, described in table. 1, and the compounds described in table. 2 (below), and one or more of the active ingredients described above can be used, for example, in the form of a single ready-mix, in the form of a combination spray mixture that consists of separate formulations based on the individual active ingredients in component form, such as a tank mixture, and as a combined use of individual active ingredients when applied in a sequential manner, i.e. one after another, over a reasonably short period, namely a few hours or days. The order of application of compounds of formula (I), selected from compounds from 1.a.01 - 1.a.32 to 1.z.01 - 1.Z.32, described in table. 1, and the compounds described in table. 2 (below), and the active ingredient(s) described above are not essential to the practice of the present invention.

A preferred composition comprises a mixture of components (A) and (B), wherein component (A) is a compound of formula (I) described above, and component (B) is selected from benzovindiflupyr, isopyrazam, pidiflumetofen, azoxystrobin, sedaxane, difenoconazole, prothioconazole , chlorothalonil, fenpropidine, acibenzolar^-methyl, cyproconazole, cyprodinil, fenpropimorph, propiconazole, hexaconazole, penconazole, pyrifenox, fludioxonil, pyroquilone, tricyclazole, fluazinam, mandipropamide, mefentrifluconazole, metalaxyl, metalaxyl-M, oxadixyl, florylpicaoxamide, methyltetraprole, oxathiapiproline, paclobutrazol, sulfur, thiabendazole, Aspergillus flavus NRRL 21882 (Afla-Guard®) and Bacillus subtilis var. Amyloliquefaciens, strain FZB24 (Taegro®).

Preferably, component (A) is a compound of formula (I) described above, and component (B) is selected from benzovindiflupyr, pidiflumetofen, isopyrazam, sedaxane, difenoconazole, cyproconazole, propiconazole, azoxystrobin, metalaxyl-M, cyprodinil, chlorothalonil, oxathiapiproline, mandipropamide , tricyclazole, fluazinam, fludioxinil, prothioconazole, mefentrifluconazole, florylpicoxamide and methyltetraprole.

More specifically, component (A) is a compound selected from the group of compounds 1.a.01 - 1.a.32 to 1.z.01 - 1.Z.32 described in table. 1 (below), and component (B) is selected from benzovindiflupyr, pidiflumetofen, isopyrazam, sedaxane, difenoconazole, cyproconazole, propiconazole, azoxystrobin, metalaxyl-M, cyprodinil, chlorothalonil, oxathiapiproline, mandipropamide, tricyclazole, fluazinam, fludioxinil, ash, mefentrifluconazole, florylpicoxamide and methyltetraprole. Preferably, component (A) is a compound selected from the group described in table. 2 (below), i.e. a compound of formula I.a.19, I.c.19, I.k.19, I.m.19, I.n.19, L.o.19 or I.r.19, and component (B) selected from benzovindiflupyr, pidiflumetofen, isopyrazam, sedaxane, difenoconazole, cyproconazole, propiconazole, azoxystrobin, metalaxyl-M , cyprodinil, chlorothalonil, oxathiapiproline, mandipropamide, tricyclazole, fluazinam, fludioxinil, prothioconazole, mefentrifluconazole, florylpicoxamide and methyltetraprole.

Component (B) in combination with component (A) can increase the effectiveness of the latter against fungi and vice versa. Additionally, fungicidal compositions may be effective against a wider range of pathogenic fungi than can be controlled if each active ingredient is used individually. In general, the weight ratio of component (A) to component (B) may be from 1000:1 to 1:1000, or from 100:1 to 1:100, or from 50:1 to 1:50, or from 20:1 to 1:40, or from 20:1 to 1:20, or from 15:1 to 1:30, or from 12:1 to 1:25, or from 10:1 to 1:20, or from 5:1 to 1:15, or from 3:1 to 1:10, or from 2:1 to 1:5. Otherwise, the weight ratio of component (A) to component (B) may be from 2:1 to 1:2, or from 4:1 to 2:1, or 1:1, or 5:1,

- 26 047112 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. It should be understood that such ratios of components in the mixture include, on the one hand, ratios by weight, and also, on the other hand, molar ratios. Synergistic effects may occur between the active ingredients.

In a preferred composition, the mixture of active ingredients of components (A) and (B) as described above may contain an additional active ingredient of component (C) selected from one of benzovindiflupyr, isopyrazam, pidiflumetofen, azoxystrobin, sedaxane, difenoconazole, prothioconazole , chlorothalonil, fenpropidine, acibenzolar^-methyl, cyproconazole, cyprodinil, fenpropimorph, propiconazole, hexaconazole, penconazole, pyrifenox, fludioxonil, pyroquilone, tricyclazole, fluazinam, mandipropamide, mefentrifluconazole, metalaxyl, metalaxyl-M, oxadixyl, florylpicoxamide, methyltetraprole, oxathiapiproline, paclobutrazol, sulfur, thiabendazole, Aspergillus flavus NRRL 21882 (Afla-Guard®) and Bacillus subtilis var.

Amyloliquefaciens, strain FZB24 (Taegro®), where components (B) and (C) are not the same active ingredient.

The compositions may contain the active ingredient compounds as components (A), (B) and (C) in weight ratios selected from 20:1:1, 1:20:1, 1:1:20, 10: 1:1, 1:10:1, 1:1:10, 5:1:1, 1:5:1, 1:1:5, 2:1:1, 1:2:1, 1:1: 2 or 1:1:1. Synergistic effects may occur between the active ingredients.

The compositions of the present invention can be used in any conventional form, for example, in the form of a twin pack, dry seed treatment powder (DS), seed treatment emulsion (ES), flowable seed treatment concentrate (FS), seed treatment solution (LS ), water-dispersible seed treatment powder (WS), seed treatment capsule suspension (CF), seed treatment gel (GF), emulsion concentrate (EC), suspension concentrate (SC), suspoemulsion (SE), capsule suspension ( CS), water-dispersible granules (WG), emulsifiable granules (EG), water-in-oil emulsion (EO), oil-in-water emulsion (EW), microemulsion (ME), oil dispersion (OD), oil miscible fluid Substance (OF), Oil Miscible Liquid (OL), Soluble Concentrate (SL), Ultra Low Volume Suspension (SU), Ultra Low Volume Liquid (UL), Technical Concentrate (TK), Dispersible Concentrate (DC), Wettable Powder (WP) or any commercially feasible formulation in combination with agriculturally acceptable excipients.

Such compositions can be prepared in a conventional manner, for example, by mixing the active ingredients with appropriate inert formulation components (diluents, solvents, excipients and optionally other formulation ingredients such as surfactants, biocides, antifreeze additives, tackifiers, thickeners and compounds , which provide auxiliary effects). If long-term action is required, traditional slow-release formulations can also be used. In particular, spray formulations such as water-dispersible concentrates (e.g. EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders and granules may contain surfactants , such as wetting and dispersing agents and other compounds that provide auxiliary effects, for example, formaldehyde naphthalene sulfonate condensate, alkylaryl sulfonate, lignin sulfonate, fatty acid alkyl sulfate and ethoxylated alkyl phenol, and ethoxylated fatty alcohol.

The seed treatment composition is applied in a manner known per se for seeds, using the combination of the present invention and a diluent in a suitable form of the seed treatment composition, for example, an aqueous suspension or a dry powder form having good adhesion to the seeds. Such seed dressing compositions are known in the art. Seed dressing compositions may contain individual active ingredients or a combination of active ingredients in encapsulated form, such as capsules or slow release microcapsules.

Typically, the formulations contain from 0.01 to 90% by weight active agent, from 0 to 20% agriculturally acceptable surfactant, and from 10 to 99.99% solid or liquid inert formulation components and auxiliary(s). ) substance(s), wherein the active agent consists of at least a compound of formula (I) together with component (B) and (C) and optionally other active agents, in particular microbiocides, or preservatives, or the like. Concentrated forms of the compositions typically contain from about 2 to 80% by weight, preferably from about 5 to 70% by weight of active agent. The formulation forms used may, for example, contain from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight, of active agent. Since commercial products will preferably be formulated as concentrates, the end user will typically use diluted formulations.

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Examples

The following examples serve to illustrate the present invention.

The compounds of the present invention may differ from known compounds due to their higher potency at lower application rates, as can be verified by one skilled in the art using the experimental procedures set forth in the Examples section, using lower application rates if necessary, e.g., 50 ppm, 12. 5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm or 0.2 ppm.

The compounds of formula (I) may have a number of advantages, including, inter alia, advantageous levels of biological activity for protecting plants against diseases caused by fungi, or superior properties for use as agrochemically active ingredients (e.g., higher biological activity, preferential spectrum of activity, improved safety profile (including improved crop tolerance), improved physicochemical properties or increased biodegradability).

List of abbreviations. °C = degrees Celsius

CDC1 ₃ = chloroform-dd = doublet

HATU = 1 - [bis(dimethylamino)methylene] -\H-1,2,3 -triazolo[4,5 -Z>] pyridinium-3 oxide hexafluorophosphate m = multiplet

MHz = megahertz

m.p. = melting point ppm = parts per million q = quartet s = singlet t = triplet

Example 1. This example illustrates the preparation of 2-[(2,6-difluoro-4-pyridyl)amino]-X(2,2-dimethylcyclobutyl)-5-methylthiazol-4-carboxamide (compound 1.r. 19)

a) Preparation of methyl 2-[(2,6-difluoro-4-pyridyl)amino]-5-methylthiazole-4-carboxylate

To a mixture of methyl 2-bromo-5-methylthiazol-4-carboxylate (2.45 g, 9.9 mmol) in dioxane (350 ml) was added sequentially Xantphos (1.2 g, 2.0 mmol), tris(dibenzylideneacetone )dipalladium (0.9 g, 1.0 mmol), cesium carbonate (6.4 g, 19.7 mmol) and 4-amino-2,6-difluoropyridine (1.3 g, 9.9 mmol). The mixture was purged with argon for 20 minutes, then heated to reflux for 4 hours. The reaction mixture was cooled to room temperature and filtered through celite. The filtrate was concentrated under reduced pressure and the remainder was purified by silica gel chromatography using ethyl acetate and cyclohexane as eluents to give methyl 2-[(2,6difluoro-4-pyridyl)amino]-5-methylthiazole-4-carboxylate (1 .0 g, 3.5 mmol). ¹ H-NMR (400 MHz, CDCl ₃ ): d = 2.73 (s, 3H), 3.91 (s, 3H), 6.76 (s, 1H), 7.25 (s, 1H), 8.29 (bs, 1H).

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b) Preparation of 2-[(2,6-difluoro-4-pyridyl)amino]-5-methylthiazole-4-carboxylic acid

To a solution of methyl 2-[(2,6-difluoro-4-pyridyl)amino]-5-methylthiazole-4-carboxylate (1.8 g, 6.3 mmol) in a mixture of tetrahydrofuran (12 ml) and water (12 ml) lithium hydroxide monohydrate (0.6 g, 25 mmol) was added. The reaction mixture was stirred for 16 hours at room temperature, followed by removal of the solvents under reduced pressure. The residue was diluted with water, then 2 N was added slowly. hydrochloric acid until pH reaches 3-4. The resulting precipitate was filtered, washed with cold water and dried in a vacuum oven to give 2-[(2,6-difluoro-4pyridyl)amino]-5-methylthiazole-4-carboxylic acid (0.9 g, 5.7 mmol). ¹ H-NMR (400 MHz, d ₆ -DMSO): d = 2.63 (s, 3H), 7.28 (s, 2H), 11.33 (bs, 1H), 12.91 (bs, 1H ).

c) Preparation of 2-[(2,6-difluoro-4-pyridyl)amino]-N(2,2-dimethylcyclobutyl)-5-methylthiazol-4carboxamide (compound 1.r.19)

To a solution of 2-[(2,6-difluoro-4-pyridyl)amino]-5-methylthiazole-4-carboxylic acid (0.25 g, 0.92 mmol) in \,\-dimethylformamide (9.2 ml) added CA'-diisopropidethylamine (0.37 ml, 2.12 mmol), (2,2-dimethylcyclobutyl)ammonium chloride (0.14 g, 1.01 mmol) and HATU (0.39 g, 1.01 mmol) and the reaction mixture was stirred for 40 min at room temperature. A saturated aqueous sodium bicarbonate solution was added, followed by water, and the solution was extracted twice with ethyl acetate. The phases were separated, the organic layer was washed once with brine, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by silica gel chromatography using ethyl acetate and cyclohexane as eluents to isolate 2-[(2,6-difluoro-4-pyridyl)amino]-K-(2,2-dimethylcyclobutyl)-5-methylthiazole4-carboxamide ( 0.28 g, 0.79 mmol). ¹ H-NMR (400 MHz, CDCl3): d = 1.17 (s, 3H), 1.20 (s, 3H), 1.50 - 1.75 (m, 2H), 1.86 - 1, 92 (m, 1H), 2.29 - 2.36 (m, 1H), 2.79 (s, 3H), 4.25 - 4.31 (m, 1H), 6.87 (s, 2H) , 7.32 (d, 1H), 7.67 (s, 1H).

In table 1 below illustrates examples of individual compounds of formula (I) in accordance with the present invention.

Table 1

Selected compounds of formula (I) according to the present invention

Connection no. X R ¹ R ² R ³ R ⁴ 01 CH F N C1 n 02 CH F N C1 OSNZ 03 CH F n СНз N 04 CH F n СНз OSNZ 05 CH F OSN ₃ C1 N 06 CH F base ₃ C1 OSNZ 07 CH F OSNZ СНз n 08 CH F OSNZ СНз OSNZ 09 CH C1 n C1 n 10 CH C1 n C1 OSNZ eleven CH C1 n СНз n 12 CH C1 n СНз OSNZ 13 CH C1 OSNZ C1 n 14 CH C1 OSNZ C1 OSNZ 15 CH C1 OSNZ СНз n

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16 sn C1 OSN ₃ СНз OSNZ 17 N F n C1 n 18 N F n C1 OSNZ 19 N F n СНз n 20 N F n СНз OSNZ 21 N F OSNZ C1 n 22 N F OSNZ C1 OSNZ 23 N F OSNZ СНз n 24 N F OSNZ СНз OSNZ 25 N C1 n C1 n 26 N C1 n C1 OSNZ 27 N C1 n СНз n 28 N C1 n СНз OSNZ 29 N C1 OSNZ C1 n thirty N C1 OSNZ C1 OSNZ 31 N C1 OSNZ СНз N 32 N C1 OSNZ СНз OSNZ

where a) 32 compounds of formula (I.a):

where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. 1. b) 32 compounds of formula (Ib):

R ² where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. 1.

c) 32 compounds of formula (I.c):

where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. 1. d) 32 compounds of formula (Id):

R ² where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. 1.

e) 32 compounds of formula (I.e):

where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. 1.

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f) 32 compounds of formula (I.f):

where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. 1. g) 32 compounds of formula (Ig):

where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. 1. h) 32 compounds of formula (Ih):

where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. 1. i) 32 compounds of formula (Ii):

where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. 1. j) 32 compounds of formula (Ij):

where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. 1. k) 32 compounds of formula (Ik):

1.

where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. m) 32 compounds of formula (Im):

where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table.

1.

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n) 32 compounds of formula (I.n):

1.

where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. o) 32 compounds of formula (Io):

1.

where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. p) 32 compounds of formula (Ip):

1.

where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. q) 32 compounds of formula (Iq):

where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. 1. r) 32 compounds of formula (Ir):

where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. 1. s) 32 compounds of formula (Is):

where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. 1.

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t) 32 compounds of formula (I.t):

where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. 1. u) 32 compounds of formula (Iu):

where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. 1. v) 32 compounds of formula (Iv):

where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. 1. w) 32 compounds of formula (Iw):

1.

where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. x) 32 compounds of formula (Ix):

R ¹

1.

,χ) where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. y) 32 compounds of formula (Iy):

R ¹

Y) where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. 1. z) 32 compounds of formula (Iz):

- 33 047112 where R ¹ , R ² , R ³ , R ⁴ and X are as defined in table. 1.

Throughout this description, temperature values are given in degrees Celsius (°C), and m/p. means melting point. LC/MS means liquid chromatography - mass spectrometry, and the description of the device and method is as follows: (ACQUITY UPLC from Waters, Phenomenex Gemini C18, particle size 3 μm, 110 angstroms, column 30x3 mm, 1.7 ml/min, 60°C , H ₂ O + 0.05% HCOOH (95%)/CH ₃ CN/Me0H 4:1 + 0.04% HCOOH (5%) - 2 min - CH ₃ CN/MeOH 4:1 + 0.04% HCOOH (5%) - 0.8 min, ACQUITY SQD mass spectrometer from Waters, ionization method: electrospray (ESI), polarity: positive ions, capillary voltage (kV) 3.00, cone voltage (V) 20, 00, extractor voltage (V) 3.00, source temperature (°C) 150, desolvation temperature (°C) 400, gas flow in the cone (l/h) 60, desolvation gas flow (l/h) 700)) .

Table 2

Melting point and LC/MS data (R _t = retention time) for selected compounds from the table. 1

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Ln. 19

1.0.19

I.r.19

Cl

2-[(2,6-difluoro-4pyridyl)amino]-5 methyl-N-[2-(3-methyl-2 thienyl)cyclobutyl]thiazole-4-carboxamide

N-[2-(2,4dichlorophenyl)cyclobutyl]-2-[(2,6-difluoro-4pyridyl)amino]-5 methyl-thiazol-4carboxamide

2-[(2,6-difluoro-4pyridyl)amino]-N-(2,2dimethylcyclobutyl)-5 methyl-thiazol-4carboxamide

H

R _t = 1.90 min;

MS: mass/charge = 469 (M+l)

R _t = 1.80 min;

MS: mass/charge = 421 (M+l)

R _t = 1.09 min;

MS: mass/charge = 353 (M+l)

Examples of compositions.

Wettable powders

a)

b)

c)

active ingredient [compound of formula (I)] 25% 50% 75% sodium lignosulfonate 5% 5% - sodium lauryl sulfate 3% - 5% sodium diisobutylnaphthalene sulfonate - 6% 10% polyethylene glycol phenol ether - 2% - (7-8 mol ethylene oxide) highly dispersed silicic acid 5% 10% 10% kaolin 62% 27% -

The active ingredient is thoroughly mixed with the excipients and the mixture is thoroughly ground in a suitable mill to obtain wettable powders which can be diluted with water to obtain suspensions of the required concentration.

Powders for dry seed treatment A) b) With) active ingredient [compound of formula (I)] 25% 50% 75% light mineral oil 5% 5% 5% highly dispersed silicic acid 5% 5% - kaolin 65% 40% - talc 20%

The active ingredient is thoroughly mixed with the excipients and the mixture is thoroughly ground in a suitable mill to obtain powders that can be used directly for seed treatment.

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Emulsifiable concentrate active ingredient [compound of formula (I)] 10% polyethylene glycol octylphenol ether 3% (4-5 mol ethylene oxide) calcium dodecylbenzenesulfonate 3% castor oil polyglycol ether 4% (35 mol ethylene oxide) cyclohexanone 30% xylene mixture 50%

From this concentrate, by diluting with water, one can obtain emulsions of any required degree of dilution, which can be used to protect plants. Dust preparations a) b) c) active ingredient [compound of formula (I)] 5% 6%4% talc 95% -kaolin - 94% mineral filler - - 96%

Ready-to-use powdered preparations are prepared by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry seed dressing options.

Extruded granules active ingredient [compound 15% of formula (I)] sodium lignosulfonate 2% carboxymethylcellulose 1% kaolin 82%

The active ingredient is mixed and crushed with the excipients and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air. Coated granules active ingredient [compound 8% of formula (I)] polyethylene glycol (MW 200) 3% kaolin 89%

The finely ground active ingredient is evenly applied to the kaolin moistened with polyethylene glycol in a mixing device. In this way, non-dust-like, coated granules are obtained.

Suspension concentrate active ingredient [compound of formula (I)] 40% propylene glycol 10% polyethylene glycol nonylphenol ether (15 mol 6% ethylene oxide) sodium lignosulfonate 10% carboxymethylcellulose 1% silicone oil (as a 75% emulsion in water) 1% water 32%

The finely divided active ingredient is thoroughly mixed with the excipients to obtain a suspension concentrate from which suspensions of any desired degree of dilution can be prepared by dilution with water. With the help of such diluted solutions, living plants, as well as plant propagation material, can be treated and protected from contamination by microorganisms by spraying, watering or immersing.

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Flowable seed treatment concentrate active ingredient [compound of formula (I)] 40% propylene glycol 5% copolymer of butanol and PO/EO 2% trpstprolphenol with 10-20 moles of EO 2%

1,2-benzisothiazolpn-3-one (as a 20% solution in water) 0.5% calcium salt of monoazopigment 5% silicone oil (as a 75% emulsion in water) 0.2% water 45.3%

The finely ground active ingredient is thoroughly mixed with the excipients to obtain a suspension concentrate, from which suspensions of any desired degree of dilution can be obtained by dilution with water. With the help of such diluted solutions, living plants, as well as plant propagation material, can be treated and protected from contamination by microorganisms by spraying, watering or immersing.

Slow release capsule suspension.

Mix 28 parts of the combination of the compound of formula (I) with 2 parts of an aromatic solvent and 7 parts of a mixture of toluene diisocyanate/polymethylene polyphenyl isocyanate (8:1). This mixture is emulsified in a mixture of 1.2 parts polyvinyl alcohol, 0.05 parts defoamer and 51.6 parts water to obtain particles of the required size. To this emulsion is added a mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts water. The mixture is shaken until the polymerization reaction is complete.

The resulting capsule suspension is stabilized by adding 0.25 parts thickener and 3 parts dispersant. The composition of the capsule suspension contains 28% active ingredients. The average diameter of capsules is 8-15 microns.

The resulting composition is applied in the form of an aqueous suspension to the seeds in a device suitable for this purpose.

Biological examples.

Treatment to prevent infection of leaf disk/wheat/Blumeria graminis f. sp. tritici (Erysiphe graminis f. sp. tritici) (powdery mildew of wheat).

Kanzler wheat leaf segments were plated on agar in a multiwell plate (24-well format) and sprayed with test compound formulated with DMSO and Tween 20 and diluted in water. Leaf discs were inoculated by shaking powdery mildew-infected plants over test plates 1 day after application of the formulation. The inoculated leaf disks were incubated at 20°C and 60% relative humidity under a 24-hour dark followed by 12-hour light/12-hour dark environment in a climate chamber, and the activity of the compound was assessed as a percentage of disease control compared to untreated material when the corresponding degree of damage due to the disease appears on untreated control leaf segments (6-8 days after application of the composition).

Compounds I.a.19, I.c.19 and I.r.19 at a concentration of 200 ppm in the formulation provided at least 80% disease control in this test compared to untreated control leaf disks under the same conditions, which showed extensive disease development.

Treatment of liquid culture of Botryotinia fuckeliana (Botrytis cinerea)/(grey rot).

Fungal conidia from cryogenic storage were directly mixed with nutrient broth (Vogel broth). After adding the solution (DMSO) of the test compound, nutrient broth containing fungal spores was added to a microtiter plate (96-well format). Test plates were incubated at 24°C and growth inhibition was determined photometrically 3-4 days after application of the composition.

Compounds I.e.19 and I.r.19 at a concentration of 200 ppm in the formulation provided at least 80% disease control in this test compared to untreated control leaf discs under the same conditions, which demonstrated extensive mycelial growth.

Treatment of liquid culture of Glomerella lagenarium (Colletotrichum lagenarium)/(anthracnose).

Fungal conidia from cryogenic storage were directly mixed with nutrient broth (potato dextrose broth, PDB). After adding the solution (DMSO) of the test compound, nutrient broth containing fungal spores was added to a microtiter plate (96-well format). Test plates were incubated at 24°C and growth inhibition was determined photometrically 3-4 days after application of the composition.

Compounds I.a.19, I.c.19, I.o.19 and I.r.19 at a concentration of 200 ppm in the formulation provided at least 80% disease control in this test compared to untreated control leaf disks under the same conditions, which showed extensive disease development.

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Treatment to prevent infection of leaf disk/rice/Magnaporthe grisea (Pyricularia oryzae)/(rice blast).

Ballila rice leaf segments were placed on agar in a multi-well plate (24-well format) and sprayed with a test compound formulated with DMSO and Tween 20 and diluted in water. Leaf segments were inoculated with a suspension of fungal spores 2 days after application of the composition. The inoculated leaf segments were incubated at 22°C and 80% relative humidity under a 24 hour dark followed by 12 hour light/12 hour dark environment in a climate chamber and the activity of the compound was assessed as a percentage of disease control compared to untreated material when the corresponding degree of damage due to the disease appears on untreated control leaf segments (5-7 days after application of the composition).

Compounds I.a.19, I.e.19 and I.r.19 at a concentration of 200 ppm in the formulation provided at least 80% disease control in this test compared to untreated control leaf disks under the same conditions, which showed extensive disease development.

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

Fungal conidia from cryogenic storage were directly mixed with nutrient broth (potato dextrose broth, PDB). After adding the solution (DMSO) of the test compound, nutrient broth containing fungal spores was added to a microtiter plate (96-well format). Test plates were incubated at 24 °C and growth inhibition was determined photometrically 4-5 days after application of the composition.

Compounds I.a.19, I.m.19, I.o.19 and I.r.19 at a concentration of 200 ppm in the formulation provided at least 80% disease control in this test compared to untreated control leaf discs under the same conditions, which demonstrated extensive mycelial growth.

Liquid culture treatment/Mycosphaerella arachidis (Cercospora arachidicola)/(early leaf blight).

Fungal conidia from cryogenic storage were directly mixed with nutrient broth (potato dextrose broth, PDB). After adding the solution (DMSO) of the test compound, nutrient broth containing fungal spores was added to a microtiter plate (96-well format). Test plates were incubated at 24°C and growth inhibition was determined photometrically 4-5 days after application of the composition.

Compound I.r.19 at a concentration of 200 ppm in the formulation provided at least 80% disease control in this trial compared to untreated control leaf discs under the same conditions, which demonstrated extensive mycelial growth.

Treatment of liquid culture Mycosphaerella graminicola (Septoria 1gPcs)/(septoria).

Fungal conidia from cryogenic storage were directly mixed with nutrient broth (potato dextrose broth, PDB). After adding the solution (DMSO) of the test compound, nutrient broth containing fungal spores was added to a microtiter plate (96-well format).

Test plates were incubated at 24°C and growth inhibition was determined photometrically 4-5 days after application of the composition.

Compounds I.a.19, I.c.19, I.k.19, I.o.19 and I.r.19 at a concentration of 200 ppm in the formulation provided at least 80% disease control in this test compared to untreated control leaf discs under the same conditions, which demonstrated extensive mycelial growth.

Treatment to prevent leaf disk/wheat infection (Phaeosphaeria nodorum (Septoria nodorum)/(septoria glume blight) Leaf segments of wheat cv. Kanzler were placed on agar in a multi-well plate (24-well format) and sprayed with the formulated test compound diluted in water. Leaf discs were inoculated with a suspension of fungal spores 2 days after application of the composition. Inoculated leaf discs were incubated at 20°C and 75% relative humidity under a 12-hour light/12-hour dark cycle in a climate chamber and compound activity was assessed as a percentage of disease control compared to untreated material when developed on untreated control leaves. discs of the corresponding degree of damage due to disease (5-7 days after applying the composition).

Connection I.r. 19 at a concentration of 200 ppm in the formulation provided at least 80% disease control in this trial compared to untreated control leaf disks under the same conditions, which demonstrated extensive disease development.

Treatment to prevent infection of leaf disk/wheat/Puccinia recondita f. sp. 1p11a/(brown rust).

Leaf segments of the wheat variety Kanzler were placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. Leaf discs were inoculated with a suspension of fungal spores 1 day after application of the composition. Inoculiro

- 38 047112 bathed leaf segments were incubated at 19°C and 75% relative humidity with a light regime of 12 hours light/12 hours dark in a climate chamber and the activity of the compound was assessed as an indicator of disease control, expressed as a percentage, compared to untreated material when developed on untreated control segments of leaves corresponding to the degree of damage due to the disease (7-9 days after application of the composition).

Compounds I.a.19, I.c.19 and I.r. 19 at a concentration of 200 ppm in the formulation provided at least 80% disease control in this trial compared to untreated control leaf discs under the same conditions, which demonstrated extensive disease development.

Claims (9)

1. Compound of formula (I) where R ¹ represents chlorine or fluorine; R ² represents hydrogen; R ³ represents ^-C^alkyl; R ⁴ represents hydrogen; R ⁵ represents hydrogen, halogen, ^-^alkyl, C ₂ -C6alkenyl, C ₂ -C6alkynyl, C1- _C4 haloalkyl, C ₂ -C6haloalkenyl, C ₂ -C6haloalkynyl, hydroxyC ₁ -C ₄ alkyl, cyanoC ₁ -C ₄ alkyl, C ₃ -C6 cycloalkyl, phenyl or heteroaryl, where the heteroaryl moiety is a 5- or 6-membered aromatic monocyclic ring containing 1, 2, 3 or 4 heteroatoms individually selected from nitrogen, oxygen and sulfur, and where each from C3-C6cycloalkyl, phenyl and heteroaryl fragments is optionally substituted with 1-3 groups represented by R ⁷ ; R ⁶ represents hydrogen, halogen, ^-C^alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C1-C ₄ haloalkyl, C 2 -C ₆ haloalkenyl, C _{2 -C 6} haloalkynyl, hydroxyC1- C ₄ alkyl, cyanoC1-C ₄ alkyl, C ₃ -C ₆ cycloalkyl, phenyl or heteroaryl, where the heteroaryl moiety is a 5- or 6-membered aromatic monocyclic ring containing 1, 2, 3 or 4 heteroatoms, individually selected from nitrogen, oxygen and sulfur, and wherein each of the C ₃ -C ₆ cycloalkyl, phenyl and heteroaryl moieties is optionally substituted with 1-3 groups represented by R ⁷ ; R ⁷ represents halogen, cyano, hydroxyl, ^-^alkyl, CrC^alkoxy or C ₃ -C ₄ cycloalkyl; X represents C-H; or a salt or N-oxide thereof. 2. The compound according to claim 1, where R ¹ represents fluorine. 3. A compound according to claim 1 or 2, where R ⁵ represents hydrogen, halogen, ^-C^alkyl, C ₂ -C ₆ alkynyl, C ₃ -C ₄ cycloalkyl or phenyl, where each of C ₃ -C ₄ cycloalkyl and phenyl fragments are optionally substituted with 1-3 groups represented by R ⁷ . 4. A compound according to any one of claims 1-3, where R ⁷ represents halogen, ^-^alkyl or ('rC ₃ a.1koxy. 5. A compound according to any one of claims 1-4, where if R ⁵ represents hydrogen or CrC^kyl, then R ⁶ represents ^-^alkyl, phenyl or thienyl, where the phenyl and thienyl fragments are optionally substituted with 1 or 2 groups, selected from R ⁷ . 6. A compound according to any one of claims 1 to 5, where R ³ represents methyl. 7. A fungicidal composition containing a fungicidal effective amount of a compound of formula (I) according to any one of paragraphs. 1-6. 8. A method for controlling or preventing infection of beneficial plants by phytopathogenic microorganisms, wherein a fungicidal effective amount of a compound of formula (I) according to any one of claims 1 to 6 or a composition according to claim 7 is applied to the plants, their parts or their place of growth. 9. Use of a compound of formula (I) according to any one of claims 1 to 6 as a fungicide.