WO2020208095A1

WO2020208095A1 - Microbiocidal picolinamide derivatives

Info

Publication number: WO2020208095A1
Application number: PCT/EP2020/060071
Authority: WO
Inventors: Clemens Lamberth; Renaud Beaudegnies; Stefano RENDINE; Mathias Blum; Martin Pouliot
Original assignee: Syngenta Crop Protection AG Switzerland
Current assignee: Syngenta Crop Protection AG Switzerland
Priority date: 2019-04-10
Filing date: 2020-04-08
Publication date: 2020-10-15
Anticipated expiration: 2021-10-10

Abstract

A diastereomer, or mixture of diastereomers, of the compound of formula (I), wherein the substituents are as defined in claim 1, useful as pesticides, and especially fungicides.

Description

Microbiocidal picolinamide derivatives

The present invention relates to diastereomeric microbiocidal picolinamide derivatives, e.g., as active ingredients, which have microbiocidal activity, in particular fungicidal activity. The invention also relates to the preparation of these diastereomeric picolinamide derivatives, to agrochemical compositions which comprise at least one of the diastereomeric picolinamide derivatives and to uses of the diastereomeric picolinamide derivatives or compositions thereof in agriculture or horticulture for controlling or preventing the infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, preferably fungi.

Picolinamide compounds as fungicidal agents are described in WO 2016/109288, WO 2016/109289, WO 2016/109300, WO 2016/109301 , WO 2016/109302 and WO 2016/109303.

According to the present invention, there is provided a diastereomer, or mixture of diastereomers, of the compound of formula (I):

wherein,

R¹ is hydroxy, C2-C6acyloxy, C2-C6haloacyloxy, Ci-C6alkoxyCi-C6alkoxy, Ci-C6alkoxyCi- C6alkoxyCi-C6alkoxy, Ci-C6haloalkoxyCi-C6alkoxy, Ci-C6alkoxyCi-C6haloalkoxy, C2-C6acyloxyCi- C6alkoxy, C2-C6haloacyloxyCi-C6alkoxy, or C2-C6acyloxyCi-C6haloalkoxy;

R² is Ci-Ci2alkyl, Cs-Cscycloalkyl, Ci-C6haloalkyl, Ci-C6alkoxyCi-C6alkyl, or C3- Cehalocycloalkyl;

R³ is Ci-Ci2alkyl or Cs-Cscycloalkyl;

R⁴ is heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1 , 2, 3 or 4 heteroatoms individually selected from N, O and S, and wherein the heteroaryl moiety is optionally substituted by 1 , 2 or 3 substituents, which may be the same or different, selected from R⁵;

R⁵ is hydroxy, halogen, cyano, Ci-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, Ci-C₄haloalkyl, cyanoCi- Cealkyl, hydroxyCi-Cealkyl, or Ci-C₄alkoxyCi-C6alkyl; or a salt or an N-oxide thereof.

Surprisingly, it has been found that the novel diastereomers, or mixtures of diastereomers, of compounds of formula (I) have, for practical purposes, a very advantageous level of biological activity for protecting plants against diseases that are caused by fungi.

According to a second aspect of the invention, there is provided an agrochemical composition comprising a fungicidally effective amount of a diastereomer, or mixture of diastereomers, of the compound of formula (I) according to the present invention. Such an agricultural composition may further comprise at least one additional active ingredient and/or an agrochemically-acceptable diluent or carrier.

According to a third aspect of the invention, there is provided a method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a fungicidally effective amount of a diastereomer, or mixture of diastereomers, of the compound of formula (I), or a composition comprising this compound as active ingredient, is applied to the plants, to parts thereof or the locus thereof.

According to a fourth aspect of the invention, there is provided the use of a diastereomer, or mixture of diastereomers, of the compound of formula (I) as a fungicide. According to this particular aspect of the invention, the use may exclude methods for the treatment of the human or animal body by surgery or therapy.

In some aspects of the invention, there may be provided a single diastereomer of a compound of formula (I).

In other aspects of the invention, there may be provided a mixture of two or more diastereomers of a compound of formula (I).

Where substituents are indicated as being“optionally substituted”, this means that they may or may not carry one or more identical or different substituents, e.g., one, two or three R⁵ substituents. For example, Ci-C6alkyl substituted by 1 , 2 or 3 halogens, may include, but not be limited to, -CH₂CI, -CHCI₂, -CCI3, -CH2F, -CHF2, -CF3, -CH2CF3 or -CF2CH3 groups. As another example, Ci-C6alkoxy substituted by 1 , 2 or 3 halogens, may include, but not be limited to, CH₂CIO-, CHCI₂O-, CCI3O-, CH₂FO-, CHF₂O- , CF3O-, CF3CH₂O- or CH3CF₂O- groups.

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

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

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

As used herein, the term "Ci-C6alkyl" refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing no unsaturation, having from one to six carbon atoms, and which is attached to the rest of the molecule by a single bond. The terms "Ci-Ci2alkyl" and "Ci-C₄alkyl" are to be construed accordingly. Examples of Ci-C6alkyl include, but are not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl and the isomers thereof, for example, iso-propyl, isobutyl, sec-butyl, tert-butyl or iso-amyl. A“Ci-C6alkylene” group refers to the corresponding definition of Ci-C6alkyl, except that such radical is attached to the rest of the molecule by two single bonds. The term “Ci-C2alkylene” is to be construed accordingly. Examples of Ci-C6alkylene, include, but are not limited to, -CH2-, -CH2CH2- and -(CH₂)3-.

As used herein, the term "C2-C6alkenyl" refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one double bond that can be of either the (E)- or (^-configuration, having from two to six carbon atoms, which is attached to the rest of the molecule by a single bond. Examples of C2-C6alkenyl include, but are not limited to, ethenyl (vinyl), prop-1 -enyl, prop-2-enyl (allyl), and but-1 -enyl.

As used herein, the term "C2-C6alkynyl" refers to a straight or branched hydrocarbon chain radical group 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. Examples of C2-C6alkynyl include, but are not limited to, ethynyl, prop-1 -ynyl, and but-1 -ynyl.

As used herein, the term "Cs-Cscycloalkyl" refers to a radical which is a monocyclic saturated ring system and which contains 3 to 8 carbon atoms. The term “C3-C6cycloalkyl” is to be construed accordingly. Examples of C3-C8cycloalkyl include, but are not limited to, cyclopropyl, 1 -methylcyclopropyl, 2-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.

As used herein, the term "Ci-C6haloalkyl” refers to Ci-C6alkyl radical as generally defined above substituted by one or more of the same or different halogen atoms. The terms“Ci-C₄haloalkyl” and“Ci- C2haloalkyl” are to be construed accordingly. Examples of Ci-C6haloalkyl include, but are not limited to fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl.

As used herein, the term "Ci-C6alkoxy" refers to a radical of the formula -OR_a where R_a is a Ci- C6alkyl radical as generally defined above. The term "Ci-C₄alkoxy" is to be construed accordingly. Examples of Ci-C6alkoxy include, but are not limited to, methoxy, ethoxy, 1 -methylethoxy (iso-propoxy), propoxy, butoxy, 1 -methylpropoxy and 2-methylpropoxy.

As used herein, the term“Ci-C6alkoxyCi-C6alkyl” refers to a radical of the formula RbO-R_a- where Rb is a Ci-C6alkyl radical as generally defined above, and R_a is a Ci-C6alkylene radical as generally defined above. Examples of “Ci-C6alkoxyCi-C6alkyl” include, but are not limited to methoxymethyl, ethoxymethyl and methoxyethyl.

As used herein, the term "Ci-C6alkoxyCi-C6alkoxy" refers to a radical of the formula RbO-R_aO- where Rb is a Ci-C6alkyl radical as generally defined above, and R_a is a Ci-C6alkylene radical as generally defined above. Examples of Ci-C6alkoxyCi-C6alkoxy include, but are not limited to, methoxymethoxy, ethoxymethoxy and methoxyethoxy.

As used herein, the term“Ci-C6alkoxyCi-C6alkoxyCi-C6alkoxy” refers to a radical of the formula RcO-RbO-R_aO- where R_c is a Ci-C6alkyl radical as generally defined above, and R_a and Rb are Ci- C6alkylene radicals as generally defined above. Examples of Ci-C6alkoxyCi-C6alkoxyCi-C6alkoxy include, but are not limited to, methoxyethoxymethoxy. As used herein, the term“Ci-C6haloalkoxyCi-C6alkoxy” refers to a radical of the formula RbO- RaO-, where R_a is a Ci-C6alkylene radical as generally defined above and Rb is a Ci-C6alkyl radical as generally defined above substituted by one or more of the same or different halogen atoms. Examples of Ci-C6haloalkoxyCi-C6alkoxy groups include, but not limited to trifluoromethoxymethoxy.

As used herein, the term“Ci-C6alkoxyCi-C6haloalkoxy” refers to a radical of the formula R_aO- RbO-, where R_a is a Ci-C6alkyl radical as generally defined above and Rb is a Ci-C6alkylene radical as generally defined above substituted by one or more of the same or different halogen atoms. Examples of Ci-C6alkoxyCi-C6haloalkoxy groups include, but not limited to methoxydifluoromethoxy.

As used herein, the term“C₂-C6acyl” refers to a radical R_aC(=0)-, where R_a is a Ci-Csalkyl as generally defined above. Acyl groups include, but are not limited to, acetyl and propanoyl.

As used herein, the term "C₂-C6acyloxy" refers to a radical of the formula -OR_a where R_a is a C₂- C6acyl radical as generally defined above. C₂-C6acyloxy groups include, but are not limited to, acetoxy, propanoyloxy, isopropanoyloxy, and butanoyloxy.

As used herein, the term“C₂-C6haloacyloxy” refers to a radical of the formula R_aC(=0)0-, where R_a is Ci-Csalkyl radical as generally defined above substituted by one or more of the same or different halogen atoms. C₂-C6haloacyloxy groups include, but are not limited to trifluoroacetoxy.

As used herein, the term "C₂-C6acyloxyCi-C6alkoxy" refers to a radical of the formula R_aC(=0)0Rb0- where R_a is a Ci-Csalkyl radical as generally defined above and where Rb is a Ci- C6alkylene radical as generally defined above.

As used herein, the term "C₂-C6haloacyloxyCi-C6alkoxy" refers to a radical of the formula R_aC(=0)0Rb0- where R_a is a Ci-Csalkyl radical as generally defined above substituted by one or more of the same or different halogen atoms, and Rb is a Ci-C6alkylene radical as generally defined above.

As used herein, the term "C₂-C6acyloxyCi-C6haloalkoxy" refers to a radical of the formula R_aC(=0)0Rb0- where R_a is a Ci-Csalkyl radical as generally defined above, and Rb is a Ci-C6alkylene radical as generally defined above substituted by one or more of the same or different

As used herein, the term“cyanoCi-Cealkyl” refers to a Ci-C6alkylene radical as generally defined above substituted by one or more cyano groups as defined above.

As used herein, the term “hydroxyCi-Cealkyl” refers to a Ci-C6alkylene radical as generally defined above substituted by one or more hydroxy groups as defined above.

As used herein, the term "heteroaryl" refers to a 5- or 6-membered aromatic monocyclic ring radical which comprises 1 , 2, 3 or 4 heteroatoms individually selected from N, O and S. The heteroaryl radical may be bonded to the rest of the molecule via a carbon atom or heteroatom. Examples of heteroaryl include, but are not limited to, furanyl, thiophenyl, imidazolyl, oxadiazolyl, pyridyl, pyrrolyl, pyrazolyl, thiazolyl, oxazolyl, pyridazinyl, pyrimidinyl.

As used herein, =0 means an oxo group, e.g., as found in a carbonyl (-C(=0)-) group.

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. Also, atropisomers may occur as a result of restricted rotation about a single bond. Formula (I) is intended to include all those possible isomeric forms and mixtures thereof. The present invention includes all those possible isomeric forms and mixtures thereof for a compound of formula (I). Likewise, formula (I) is intended to include all possible tautomers. The present invention includes all possible tautomeric forms for a compound of formula (I).

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

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

The following list provides definitions, including preferred definitions, for substituents R¹ , R², R³, R⁴, and R⁵, with reference to compounds of formula (I). For any one of these substituents, any of the definitions given below may be combined with any definition of any other substituent given below or elsewhere in this document.

R¹ is hydroxy, C2-C6acyloxy, C2-C6haloacyloxy, Ci-C6alkoxyCi-C6alkoxy, Ci-C6alkoxyCi- C6alkoxyCi-C6alkoxy, Ci-C6haloalkoxyCi-C6alkoxy, Ci-C6alkoxyCi-C6haloalkoxy, C2-C6acyloxyCi- C6alkoxy, C2-C6haloacyloxyCi-C6alkoxy or C2-C6acyloxyCi-C6haloalkoxy. Preferably, R¹ is hydroxy, C2- C₄acyloxy, C₂-C₄haloacyloxy, Ci-C₄alkoxyCi-C₄alkoxy, Ci-C3alkoxyCi-C₄alkoxyCi-C3alkoxy, Ci- C₄haloalkoxyCi-C₄alkoxy, Ci-C₄alkoxyCi-C₄haloalkoxy, C₂-C₄acyloxyCi-C₄alkoxy, C2-

C₄haloacyloxyCi-C₄alkoxy or C₂-C₄acyloxyCi-C₄haloalkoxy. More preferably, R¹ is hydroxy, acetoxy, propanoyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, acetoxymethoxy, propanoyloxymethoxy, 2- methylpropanoyloxymethoxy, or methoxyethoxymethoxy. More preferably still, hydroxy, acetoxy, propanoyloxy, acetoxymethoxy, propanoyloxymethoxy, or 2-methyl-propanoyloxymethoxy. Even more preferably, R¹ is hydroxy, acetoxy, or 2-methylpropanoyloxymethoxy, and most preferably, R¹ is hydroxy or 2-methylpropanoyloxymethoxy.

R² is Ci-Ci2alkyl, Cs-Cscycloalkyl, Ci-C6haloalkyl, Ci-C6alkoxyCi-C6alkyl, or C3- Cshalocycloalkyl. Preferably, R² is Ci-C₄alkyl, C3-C6cycloalkyl, Ci-C₄haloalkyl, Ci-C₄alkoxyCi-C₄alkyl or C3-C6halocycloalkyl. More preferably, R² is methyl, ethyl, cyclopropyl, difluoromethyl, trifluoromethyl, methoxymethyl, ethoxymethyl, ethoxymethyl or fluorocyclopropyl. Even more preferably, R² is methyl or ethyl, and in particular, R² is methyl.

R³ is Ci-Ci2alkyl or Cs-Cscycloalkyl. Preferably, R³ is Ci-C6alkyl, or C3-C6cycloalkyl. More preferably, R³ is Ci-Csalkyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, even more preferably, methyl, ethyl, n-propyl, isopropyl, 1 -ethylpropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. More preferably still, R³ is methyl, ethyl, n-propyl, isopropyl, 1 -ethylpropyl, tert-butyl, cyclopropyl, or cyclohexyl. Even more preferably still, R³ is methyl, ethyl, n-propyl, isopropyl, 1 - ethylpropyl, or tert-butyl, even more preferably, methyl or isopropyl, and most preferably methyl.

In one embodiment, R² and R³ are each independently Ci-C₄alkyl. Preferably, R² and R³ are each independently methyl or ethyl, and most preferably, methyl. R⁴ is heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1 , 2, 3 or 4 heteroatoms individually selected from N, O and S, and wherein the heteroaryl moiety is optionally substituted by 1 , 2 or 3 substituents, which may be the same or different, selected from R⁵. Preferably, R⁴ is heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1 , 2 or 3 heteroatoms individually selected from N, O and S, and wherein the heteroaryl moiety is optionally substituted by 1 , 2 or 3 substituents, which may be the same or different, selected from R⁵. More preferably, R⁴ is heteroaryl, wherein the heteroaryl moiety is a 6-membered aromatic ring which comprises 1 or 2 heteroatoms individually selected from N, O and S, and wherein the heteroaryl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R⁵. Even more preferably, R⁴ is pyrrolyl, furanyl, thienyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, isoxazolyl, isothiazolyl, pyridinyl, or pyrimidyl, optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R⁵. More preferably still, R⁴ is pyridyl is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R⁵.

In a further preferable set of embodiments, R⁴ is 2-pyridyl, 3-chloro-2-pyridyl, 5-chloro-2-pyridyl, 3,5-dichloro-2-pyridyl, 3-methyl-2-pyridyl, 5-methyl-2-pyridyl, 3,5-dimethyl-2-pyridyl, 5-chloro-3-methyl-

2-pyridyl, 3-chloro-5-methyl-2-pyridyl, 3-fluoro-2-pyridyl, 5-fluoro-2-pyridyl, 3,5-difluoro-2-pyridyl, 5- fluoro-3-methyl-2-pyridyl, 3-fluoro-5-methyl-2-pyridyl, 3-chloro-5-fluoro-2-pyridyl, 5-chloro-3-fluoro-2- pyridyl, 3-chloro-5-(trifluoromethyl)-2-pyridyl, 5-chloro-3-(trifluoromethyl)-2-pyridyl, 3-methyl-5- (trifluoromethyl)-2-pyridyl, 5-methyl-3-(trifluoromethyl)-2-pyridyl, 4-methyl-2-pyridyl, 4-chloro-2-pyridyl, 4-fluoro-2-pyridyl, 3-pyridyl, 2-methyl-3-pyridyl, 6-methyl-3-pyridyl, 2,6-dimethyl-3-pyridyl, 2-chloro-3- pyridyl, 6-chloro-3-pyridyl, 2,6-dichloro-3-pyridyl, 2-fluoro-3-pyridyl, 6-fluoro-3-pyridyl, 2,6-difluoro-3- pyridyl, 4-methyl-3-pyridyl, 4,6-dimethyl-3-pyridyl, 4,6-dichloro-3-pyridyl, 4-fluoro-3-pyridyl, 4,6-difluoro-

3-pyridyl, 6-(trifluoromethyl)-3-pyridyl, 4-(trifluoromethyl)-3-pyridyl, 4,6-(ditrifluoromethyl)-3-pyridyl, 4- pyridyl, 2-methyl-4-pyridyl, 3-methyl-4-pyridyl, 2,5-dimethyl-4-pyridyl, 2-chloro-4-pyridyl, 3-chloro-4- pyridyl, 2,5-dichloro-4-pyridyl, 2-fluoro-4-pyridyl, 3-fluoro-4-pyridyl, or 2,5-difluoro-4-pyridyl.

More preferably, R⁴ is 3-chloro-2-pyridyl, 5-chloro-2-pyridyl, 3,5-dichloro-2-pyridyl, 5-chloro-3- methyl-2-pyridyl, 3-chloro-5-methyl-2-pyridyl, 3-chloro-5-fluoro-2-pyridyl, 5-chloro-3-fluoro-2-pyridyl, 3- chloro-5-(trifluoromethyl)-2-pyridyl, 5-chloro-3-(trifluoromethyl)-2-pyridyl, 4-chloro-2-pyridyl, 4-fluoro-2- pyridyl, 2-chloro-3-pyridyl, 6-chloro-3-pyridyl, 2,6-dichloro-3-pyridyl, 4,6-dichloro-3-pyridyl, 2-chloro-4- pyridyl, 3-chloro-4-pyridyl, or 2,5-dichloro-4-pyridyl.

R⁵ is hydroxy, halogen, cyano, Ci-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, Ci-C₄haloalkyl, cyanoCi- Cealkyl, hydroxyCi-Cealkyl, or Ci-C₄alkoxyCi-C6alkyl. Preferably, R⁵ is hydroxy, halogen, cyano, Ci- C₄alkyl, or Ci-C₄haloalkyl. Even more preferably, R⁵ is fluoro, chloro, bromo, methyl, trifluoromethyl, or cyano. More preferably still, R⁵ is fluoro, chloro, methyl, or trifluoromethyl.

In a diastereomer, or mixture of diastereomers, of the compound of formula (I) according to the present invention, preferably:

R¹ is hydroxy, C2-C6acyloxy, C2-C6acyloxyCi-C6alkoxy or Ci-C3alkoxyCi-C₄alkoxyCi-C3lkoxy; R² is Ci-Ci2alkyl, Cs-Cscycloalkyl, Ci-C6haloalkyl, Ci-C6alkoxyCi-C6alkyl, or C3- Cshalocycloalkyl;

R³ Ci-C6alkyl or C3-C6cycloalkyl;

R⁴ is heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1 , 2, 3 or 4 heteroatoms individually selected from N, O and S, and wherein the heteroaryl moiety is optionally substituted by 1 , 2 or 3 substituents, which may be the same or different, selected from R⁵; and

R⁵ is fluoro, chloro, bromo, methyl, trifluoromethyl, or cyano.

More preferably, in a diastereomer, or mixture of diastereomers, of the compound of formula (I) according to the present invention:

R¹ is hydroxy, C₂-C6acyloxy, C₂-C6acyloxyCi-C6alkoxy, or Ci-C3alkoxyCi-C4alkoxyCi-C3lkoxy; R² is Ci-Ci₂alkyl, Cs-Cscycloalkyl, Ci-C6haloalkyl, Ci-C6alkoxyCi-C6alkyl, or C3- Cshalocycloalkyl;

R³ Ci-C6alkyl or C3-C6cycloalkyl;

R⁴ is heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1 , 2 or 3 heteroatoms individually selected from N, O and S, and wherein the heteroaryl moiety is optionally substituted by 1 , 2 or 3 substituents, which may be the same or different, selected from R⁵; and

R⁵ is fluoro, chloro, bromo, methyl, trifluoromethyl, or cyano.

More preferably, in a diastereomer, or mixture of diastereomers, of the compound of formula (I): R¹ is hydroxy, acetoxy, propanoyloxy, acetoxymethoxy, propanoyloxymethoxy, or 2-methyl- propanoyloxymethoxy;

R² is methyl, ethyl, cyclopropyl, difluoromethyl, trifluoromethyl, methoxymethyl, ethoxymethyl, ethoxymethyl, or fluorocyclopropyl;

R³ is methyl, ethyl, n-propyl, isopropyl, 1 -ethylpropyl, t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl;

R⁴ is heteroaryl, wherein the heteroaryl moiety is a 6-membered aromatic ring which comprises 1 or 2 heteroatoms individually selected from N, O and S, and wherein the heteroaryl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R⁵; and

R⁵ is fluoro, chloro, bromo, methyl, trifluoromethyl, or cyano.

In one set of embodiments, in a diastereomer, or mixture of diastereomers, of the compound of formula (I), preferably:

R¹ is hydroxy, C2-C6acyloxy or C2-C6acyloxyCi-C6alkoxy;

R³ Ci-C6alkyl or C3-C6cycloalkyl; R⁴ is 2-pyridyl, 3-chloro-2-pyridyl, 5-chloro-2-pyridyl, 3,5-dichloro-2-pyridyl, 3-methyl-2-pyridyl, 5-methyl-2-pyridyl, 3,5-dimethyl-2-pyridyl, 5-chloro-3-methyl-2-pyridyl, 3-chloro-5-methyl-2- pyridyl, 3-fluoro-2-pyridyl, 5-fluoro-2-pyridyl, 3,5-difluoro-2-pyridyl, 5-fluoro-3-methyl-2-pyridyl,

3-fluoro-5-methyl-2-pyridyl, 3-chloro-5-fluoro-2-pyridyl, 5-chloro-3-fluoro-2-pyridyl, 3-chloro-5- (trifluoromethyl)-2-pyridyl, 5-chloro-3-(trifluoromethyl)-2-pyridyl, 3-methyl-5-(trifluoromethyl)-2- pyridyl, 5-methyl-3-(trifluoromethyl)-2-pyridyl, 4-methyl-2-pyridyl, 4-chloro-2-pyridyl, 4-fluoro-2- pyridyl, 3-pyridyl, 2-methyl-3-pyridyl, 6-methyl-3-pyridyl, 2,6-dimethyl-3-pyridyl, 2-chloro-3- pyridyl, 6-chloro-3-pyridyl, 2,6-dichloro-3-pyridyl, 2-fluoro-3-pyridyl, 6-fluoro-3-pyridyl, 2,6- difluoro-3-pyridyl, 4-methyl-3-pyridyl, 4,6-dimethyl-3-pyridyl, 4,6-dichloro-3-pyridyl, 4-fluoro-3- pyridyl, 4,6-difluoro-3-pyridyl, 6-(trifluoromethyl)-3-pyridyl, 4-(trifluoromethyl)-3-pyridyl, 4,6- (ditrifluoromethyl)-3-pyridyl, 4-pyridyl, 2-methyl-4-pyridyl, 3-methyl-4-pyridyl, 2,5-dimethyl-4- pyridyl, 2-chloro-4-pyridyl, 3-chloro-4-pyridyl, 2,5-dichloro-4-pyridyl, 2-fluoro-4-pyridyl, 3-fluoro-

4-pyridyl, or 2,5-difluoro-4-pyridyl.

In a particularly preferred set of embodiments, in a diastereomer, or mixture of diastereomers, of the compound of formula (I), preferably:

R¹ is hydroxy, acetoxy, or 2-methylpropanoyloxymethoxy;

R² is methyl;

R³ is methyl;

R⁵ is fluoro, chloro, bromo, methyl, trifluoromethyl, or cyano.

In another set of embodiments, in a diastereomer, or mixture of diastereomers, of the compound of formula (I), preferably:

R¹ is hydroxy, C2-C6acyloxy or C2-C6acyloxyCi-C6alkoxy;

R² is methyl;

R³ is methyl;

R⁴ is 2-pyridyl, 3-chloro-2-pyridyl, 5-chloro-2-pyridyl, 3,5-dichloro-2-pyridyl, 3-methyl-2-pyridyl,

5-methyl-2-pyridyl, 3,5-dimethyl-2-pyridyl, 5-chloro-3-methyl-2-pyridyl, 3-chloro-5-methyl-2- pyridyl, 3-fluoro-2-pyridyl, 5-fluoro-2-pyridyl, 3,5-difluoro-2-pyridyl, 5-fluoro-3-methyl-2-pyridyl, 3-fluoro-5-methyl-2-pyridyl, 3-chloro-5-fluoro-2-pyridyl, 5-chloro-3-fluoro-2-pyridyl, 3-chloro-5- (trifluoromethyl)-2-pyridyl, 5-chloro-3-(trifluoromethyl)-2-pyridyl, 3-methyl-5-(trifluoromethyl)-2- pyridyl, 5-methyl-3-(trifluoromethyl)-2-pyridyl, 4-methyl-2-pyridyl, 4-chloro-2-pyridyl, 4-fluoro-2- pyridyl, 3-pyridyl, 2-methyl-3-pyridyl, 6-methyl-3-pyridyl, 2,6-dimethyl-3-pyridyl, 2-chloro-3- pyridyl, 6-chloro-3-pyridyl, 2,6-dichloro-3-pyridyl, 2-fluoro-3-pyridyl, 6-fluoro-3-pyridyl, 2,6- difluoro-3-pyridyl, 4-methyl-3-pyridyl, 4,6-dimethyl-3-pyridyl, 4,6-dichloro-3-pyridyl, 4-fluoro-3- pyridyl, 4,6-difluoro-3-pyridyl, 6-(trifluoromethyl)-3-pyridyl, 4-(trifluoromethyl)-3-pyridyl, 4,6- (ditrifluoromethyl)-3-pyridyl, 4-pyridyl, 2-methyl-4-pyridyl, 3-methyl-4-pyridyl, 2,5-dimethyl-4- pyridyl, 2-chloro-4-pyridyl, 3-chloro-4-pyridyl, 2,5-dichloro-4-pyridyl, 2-fluoro-4-pyridyl, 3-fluoro- 4-pyridyl, or 2,5-difluoro-4-pyridyl.

The compounds of formula (I) according to the present invention may possess three chiral centres at carbon atoms A * and ** as outlined below.

Accordingly, as already indicated, the compounds of formula (I) may exist in various diastereomeric forms, i.e., with (S,S,S)-, (S,S,R)-, (S,R,R)-, (S,R,S)-, (R,R,R)-, (R,R,S)-, (R,S,S)- or (R,S,R)- configurations present at the A, * and ** carbons, respectively. In particular, each of these configurations may be evident for compounds of formula (I) in relation to the specific combinations of definitions for R¹ , R², R³, and R⁴ for each compound described in Table 1 (a compound of formulae (1 .a.001) to (1 .bf.100)) or a compound of formula (I) described in Table 2 (below).

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

In one embodiment of the invention, the compound of formula (I) is present in the (S,S,R)- diastereomeric form.

In one embodiment of the invention, the compound of formula (I) is present in the (S,R,R)- diastereomeric form.

In one embodiment of the invention, the compound of formula (I) is present in the (S,R,S)- diastereomeric form.

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

In one embodiment of the invention, the compound of formula (I) is present in the (R,R,S)- diastereomeric form.

In one embodiment of the invention, the compound of formula (I) is present in the (R,S,S)- diastereomeric form.

In one embodiment of the invention, the compound of formula (I) is present in the (R,S,R)- diastereomeric form.

In a preferable embodiment ofthe invention, the compound of formula (I) is present in the (R,R,S)- diastereomeric form.

In a preferable embodiment of the invention, the compound of formula (I) is present in the (S,S,S)- diastereomeric form.

In a preferable embodiment of the invention, the compound of formula (I) is present in the (S,R,S)- diastereomeric form. In a preferable embodiment of the invention, the compound of formula (I) is present in the (R,S,S)- diastereomeric form.

In particular, the compounds of formula (I) may exist as a compound of formula (l-a), (l-b), (l-c), (l-d), (l-e), (l-f), (l-g), or (l-h). Compounds of formula (I) may be a mixture of compounds (l-a), (l-b), (I- c), (l-d), (l-e), (l-f), (l-g), and (l-h) in any ratio, e.g. in any molar ratio. The compound of formula (I) may be a racemic mixture of the compounds (l-a), (l-b), (l-c), (l-d), (l-e), (l-f), (l-g), and (l-h), or may be enantiomerically enriched individually for any one of the diastereomeric compounds (l-a), (l-b), (l-c), (I- d), (l-e), (l-f), (l-g), and (l-h).

Preferably, the compounds of formula (I) exist as a compound of formula (l-a), (l-b), (l-c), or (l-d). Compounds of formula (I) may be a mixture of compounds (l-a), (l-b), (l-c), and (l-d) in any ratio, e.g. in any molar ratio.

Preferably, the compound of formula (I) is a diastereoisomeric mixture of the compounds (l-a), (I- b), (l-c), and (l-d), or is enriched for any one of the compounds (l-a), (l-b), (l-c), and (l-d).

(l-c) (l-d)

Compounds of formula (l-a), (l-b), (l-c), and (l-d) may have different or similar biological activity. Compounds of formula (I) may be a mixture of compounds (l-a), (l-b), (l-c), and (l-d) in any ratio. Preferably, compounds of formula (I) may be a mixture of compounds (l-a), (l-b), (l-c), and (l-d) in a molar ratio of 99:0.3:0.3:0.3 to 0.3:99:0.3:0.3 to 0.3:0.3:99:0.3 to 0.3:0.3:0.3:99, more preferably in a molar ratio of 10:1 :1 :1 to 1 :10:1 :1 to 1 :1 :10:1 to 1 :1 :1 :10.

In one embodiment, the compounds of formula (I) may be a mixture of compounds (l-a), (l-b), (I- c), and (l-d) in a molar ratio of 9:1 :1 :1 to 1 :9:1 :1 to 1 :1 :9:1 to 1 :1 :1 :9.

In one embodiment, the compounds of formula (I) may be a mixture of compounds (l-a), (l-b), (I- c), and (l-d) in a molar ratio of 8:1 :1 :1 to 1 :8:1 :1 to 1 :1 :8:1 to 1 :1 :1 :8.

In one embodiment, the compounds of formula (I) may be a mixture of compounds (l-a), (l-b), (I- c), and (l-d) in a molar ratio of 7:1 :1 :1 to 1 :7:1 :1 to 1 :1 :7:1 to 1 :1 :1 :7.

In one embodiment, the compounds of formula (I) may be a mixture of compounds (l-a), (l-b), (I- c), and (l-d) in a molar ratio of 6:1 :1 :1 to 1 :6:1 :1 to 1 :1 :6:1 to 1 :1 :1 :6.

In one embodiment, the compounds of formula (I) may be a mixture of compounds (l-a), (l-b), (I- c), and (l-d) in a molar ratio of 5:1 :1 :1 to 1 :5:1 :1 to 1 :1 :5:1 to 1 :1 :1 :5.

In a further embodiment, the compounds of formula (I) may be a mixture of compounds (l-a), (I- b), (l-c), and (l-d) in a substantially molar ratio of 1 : 1 : 1 :1 .

Preferably the compound of formula (I) is a mixture of the compounds of formula (l-a), (l-b), (l-c), and (l-d) or is enriched for the most biologically active isomer.

In one embodiment, the compound of formula (I) is a compound of formula (l-a) in substantially pure form, e.g. it is provided substantially in the absence of the other three diastereoisomers. For example, when compound of formula (I) is a stereoisomerically enriched mixture of formula (l-a), the molar proportion of compound (l-a) compared to the total amount of all the stereoisomers is for example equal or greater than 50%, e.g. at least 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%.

In another embodiment, the compound of formula (I) is a compound of formula (l-b) in substantially pure form, e.g. it is provided substantially in the absence of the other three diastereoisomers. For example, when compound of formula (I) is a stereoisomerically enriched mixture of formula (l-b), the molar proportion of compound (l-b) compared to the total amount of all the stereoisomers is for example equal or greater than 50%, e.g. at least 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%.

In a further embodiment, the compound of formula (I) is a compound of formula (l-c) in substantially pure form, e.g. it is provided substantially in the absence of the other three diastereoisomers. For example, when compound of formula (I) is a stereoisomerically enriched mixture of formula (l-c), the molar proportion of compound l-c compared to the total amount of all the stereoisomers is for example equal or greater than 50%, e.g. at least 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%.

In a further still embodiment, the compound of formula (I) is a compound of formula (l-d) in substantially pure form, e.g. it is provided substantially in the absence of the other three diastereoisomers. For example, when compound of formula (I) is a stereoisomerically enriched mixture of formula (l-d), the molar proportion of compound (l-d) compared to the total amount of all the stereoisomers is for example equal or greater than 50%, e.g. at least 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%.

In one embodiment of the invention, the diastereomeric compound of formula (I) is a compound of formula X-l-a, wherein R¹ is selected from hydroxy, acetoxy, propanoyloxy, acetoxymethoxy, propanoyloxymethoxy, and 2-methyl-propanoyloxymethoxy:

In one embodiment of the invention, the diastereomeric compound of formula (I) is a compound of formula X-l-b, wherein R¹ is selected from hydroxy, acetoxy, propanoyloxy, acetoxymethoxy, propanoyloxymethoxy, and 2-methyl-propanoyloxymethoxy:

In one embodiment of the invention, the diastereomeric compound of formula (I) is a compound of formula X-l-c, wherein R¹ is selected from hydroxy, acetoxy, propanoyloxy, acetoxymethoxy, propanoyloxymethoxy, and 2-methyl-propanoyloxymethoxy:

In one embodiment of the invention, the diastereomeric compound of formula (I) is a compound of formula X-l-d, wherein R¹ is selected from hydroxy, acetoxy, propanoyloxy, acetoxymethoxy, propanoyloxymethoxy, and 2-methyl-propanoyloxymethoxy: In one embodiment of the invention, the diastereomeric compound of formula (I) is a compound of formula X-l-e, wherein R¹ is selected from hydroxy, acetoxy, propanoyloxy, acetoxymethoxy, propanoyloxymethoxy, and 2-methyl-propanoyloxymethoxy:

In one embodiment of the invention, the diastereomeric compound of formula (I) is a compound of formula X-l-f, wherein R¹ is selected from hydroxy, acetoxy, propanoyloxy, acetoxymethoxy, propanoyloxymethoxy, and 2-methyl-propanoyloxymethoxy:

In one embodiment of the invention, the diastereomeric compound of formula (I) is a compound of formula X-l-g, wherein R¹ is selected from hydroxy, acetoxy, propanoyloxy, acetoxymethoxy, propanoyloxymethoxy, and 2-methyl-propanoyloxymethoxy:

In one embodiment of the invention, the diastereomeric compound of formula (I) is a compound of formula X-l-h, wherein R¹ is selected from hydroxy, acetoxy, propanoyloxy, acetoxymethoxy, propanoyloxymethoxy, and 2-methyl-propanoyloxymethoxy:

Compounds of the present invention can be made as shown in the schemes below, in which, unless otherwise stated, the definition of each variable is as defined above for a compound of formula

(I)·

The compounds of formula (l-A) according to the invention, wherein R³ and R⁴ are as defined for formula (I), and R¹¹ is C2-C6acyl, C2-C6haloacyl, Ci-C6alkoxyCi-C6alkyl, Ci-C6haloalkoxyCi-C6alkyl, Ci- C6alkoxyCi-C6haloalkyl, C2-C6acyloxyCi-C6alkyl, C2-C6haloacyloxyCi-C6alkyl, or C2-C6acyloxyCi- C6haloalkyl, can be obtained by transformation of a compound of formula (I), wherein R³ and R⁴ are as defined for formula (I) and a compound of formula (II), wherein R¹¹ is C2-C6acyl, C2-C6haloacyl, Ci- C6alkoxyCi-C6alkyl, Ci-C6haloalkoxyCi-C6alkyl, Ci-C6alkoxyCi-C6haloalkyl, C2-C6acyloxyCi-C6alkyl, C2-C6haloacyloxyCi-C6alkyl, or C2-C6acyloxyCi-C6haloalkyl, and R¹² is halogen. This is shown in Scheme 1 below.

Scheme 1

The compounds of formula (I), wherein R³ and R⁴ are as defined for formula (I), can be obtained by transformation of a compound of formula (III), wherein R³ and R⁴ are as defined for formula (I), and a compound of formula (IV). This is shown in Scheme 2 below.

Scheme 2

The compounds of formula (III), wherein R³ and R⁴ are as defined for formula (I), can be obtained by transformation of a compound of formula (V), wherein R³ and R⁴ are as defined for formula (I), and with an acid. This is shown in Scheme 3 below. Scheme 3

The compounds of formula (V), wherein R³ and R⁴ are as defined for formula (I), can be obtained by transformation of a compound of formula (VI), and a compound of formula (VII), wherein R³ and R⁴ are as defined for formula (I), and with a base or a peptide coupling reagent. This is shown in Scheme 4 below.

Scheme 4

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

The compounds of formula (I) can be used in the agricultural sector and related fields of use, e.g., as active ingredients for controlling plant pests or on non-living materials for control of spoilage microorganisms or organisms potentially harmful to man. The novel compounds are distinguished by excellent activity at low rates of application, by being well tolerated by plants and by being environmentally safe. They have very useful curative, preventive and systemic properties and may be used for protecting numerous cultivated plants. The compounds of formula (I) can be used to inhibit or destroy the pests that occur on plants or parts of plants (fruit, blossoms, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time protecting also those parts of the plants that grow later, e.g., 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 plants or plant propagation material and/or harvested food crops wherein an effective amount a compound of formula (I) is applied to the plants, to parts thereof or the locus thereof.

It is also possible to use the compounds of formula (I) as fungicide. The term“fungicide” as used herein means a compound that controls, modifies, or prevents the growth of fungi. The term“fungicidally effective amount” means the quantity of such a compound or combination of such compounds that is capable of producing an effect on the growth of fungi. Controlling or modifying effects include all deviation from natural development, such as killing, retardation and the like, and prevention includes barrier or other defensive formation in or on a plant to prevent fungal infection.

It is also possible to use compounds of formula (I) as dressing agents for the treatment of plant propagation material, e.g., seeds, such as fruits, tubers or grains, or plant cuttings (e.g., rice), for the protection against fungal infections, as well as against phytopathogenic fungi occurring in the soil. The propagation material can be treated with a composition comprising a compound of formula (I) before planting: seeds, e.g., can be dressed before being sown.

The active ingredients according to the invention can also be applied to grains (coating), either by impregnating the seeds in a liquid formulation or by coating them with a solid formulation. The composition can also be applied to the planting site when the propagation material is being planted, e.g., to the seed furrow during sowing. The invention relates also to such methods of treating plant propagation material and to the plant propagation material so treated.

Furthermore, the compounds according to the present invention can be used for controlling fungi in related areas, for example in the protection of technical materials, including wood and wood related technical products, in food storage, in hygiene management.

In addition, the invention could be used to protect non-living materials from fungal attack, e.g., lumber, wall boards and paint.

The compounds of formula (I) may be, for example, effective against fungi and fungal vectors of disease as well as phytopathogenic bacteria and viruses. These fungi and fungal vectors of disease 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. inclusing 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, Laetisaria 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. cubensis, P. humuli, Pseudopeziza tracheiphila, Puccinia Spp. including P. hordei, P. recondita, P. striiformis, P. triticina, Pyrenopeziza spp, Pyrenophora spp, Pyricularia 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. prolificans, 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 present invention, target crops and/or useful plants to be protected typically comprise perennial and annual crops, such as berry plants for example blackberries, blueberries, cranberries, raspberries and strawberries; cereals for example barley, maize (corn), millet, oats, rice, rye, sorghum triticale and wheat; fibre plants for example cotton, flax, hemp, jute and sisal; field crops for example sugar and fodder beet, coffee, hops, mustard, oilseed rape (canola), poppy, sugar cane, sunflower, tea and tobacco; fruit trees for example apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; grasses for example Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St. Augustine grass and Zoysia grass; herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes for example beans, lentils, peas and soya beans; nuts for example almond, cashew, ground nut, hazelnut, peanut, pecan, pistachio and walnut; palms for example oil palm; ornamentals for example flowers, shrubs and trees; other trees, for example cacao, coconut, olive and rubber; vegetables for example asparagus, aubergine, broccoli, cabbage, carrot, cucumber, garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and vines for example grapes.

The term "useful plants" is to be understood as including also useful plants that have been rendered tolerant to herbicides like bromoxynil 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) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors) as a result of conventional methods of breeding or genetic engineering. An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding (mutagenesis) is Clearfield® summer rape (Canola). Examples of crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady®, Herculex I® and LibertyLink®.

The term "useful plants" is to be understood as including also useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.

Examples of such plants are: YieldGard® (maize variety that expresses a CrylA(b) toxin); YieldGard Rootworm® (maize variety that expresses a CrylllB(bl) toxin); YieldGard Plus® (maize variety that expresses a CrylA(b) and a Cryll IB(b1 ) toxin); Starlink® (maize variety that expresses a Cry9(c) toxin); Herculex I® (maize variety that expresses a CrylF(a2) toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a CrylA(c) toxin); Bollgard I® (cotton variety that expresses a CrylA(c) toxin); Bollgard II® (cotton variety that expresses a CrylA(c) and a CryllA(b) toxin); VIPCOT® (cotton variety that expresses a VIP toxin); NewLeaf® (potato variety that expresses a CrylllA toxin); NatureGard® Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt1 1 corn borer (CB) trait), Agrisure® RW (corn rootworm trait) and Protecta®.

The term "crops" is to be understood as including also crop plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.

Toxins that can 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 d-endotoxins, e.g. CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1 , Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonising nematodes, for example 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 (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroidoxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers, such as blockers of sodium or calcium channels, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases.

In the context of the present invention there are to be understood by d-endotoxins, for example CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1 , Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02/15701). Truncated toxins, for example a truncated CrylAb, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid replacements, preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G- recognition sequence is inserted into a Cry3A toxin (see WO 03/018810).

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

The processes for the preparation of such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. Cryl-type deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651 .

The toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects. Such insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera).

Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety that expresses a CrylAb toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a CrylAb and a Cry3Bb1 toxin); Starlink® (maize variety that expresses a Cry9C toxin); Herculex I® (maize variety that expresses a Cry1 Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a CrylAc toxin); Bollgard I® (cotton variety that expresses a Cry1 Ac toxin); Bollgard II® (cotton variety that expresses a Cryl Ac and a Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A and a CrylAb toxin); NewLeaf® (potato variety that expresses a Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt1 1 corn borer (CB) trait) and Protecta®.

Further examples of such transgenic crops are:

1 . Bt11 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer ( Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated CrylAb toxin. Bt1 1 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.

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

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

4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1 150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects.

5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1 150 Brussels, Belgium, registration number C/ES/96/02.

6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1 160 Brussels, Belgium, registration number C/NL/00/10. Genetically modified maize for the expression of the protein Cry1 F for achieving resistance to certain Lepidoptera insects and of the PAT protein for achieving tolerance to the herbicide glufosinate ammonium.

7. NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1 150 Brussels, Belgium, registration number C/GB/02/M3/03. Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810. NK603 ^c MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylAb toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.

The compounds of formula (I) according to the present invention (including any one of compounds described in Table 2 (below)) may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizi ) on soy bean plants.

In particular, transgenic soybean plants expressing toxins, for example insecticidal proteins such as delta-endotoxins, e.g. Cry1 Ac (Cry1 Ac Bt protein). Accordingly, this may include transgenic soybean plants comprising event MON87701 (see U.S. Patent No. 8,049,071 and related applications and patents, as well as WO 2014/170327 A1 (e.g., see paragraph [008] reference to Intacta RR2 PRO™ soybean)), event MON87751 (US. Patent Application Publication No. 2014/0373191) or event DAS- 81419 (U.S. Patent No. 8632978 and related applications and patents).

Other transgenic soybean plants may comprise event SYHT0H2 - HPPD tolerance (U.S. Patent Application Publication No. 2014/0201860 and related applications and patents), event MON89788 - glyphosate tolerance (U.S. Pat. No. 7,632,985 and related applications and patents), event MON87708 - dicamba tolerance (U.S. Patent Application Publication No. US 201 1/0067134 and related applications and patents), event DP-356043-5 - glyphosate and ALS tolerance (U.S. Patent Application Publication No. US 2010/0184079 and related applications and patents), event A2704-12 - glufosinate tolerance (U.S. Patent Application Publication No. US 2008/0320616 and related applications and patents), event DP-305423-1 - ALS tolerance (U.S. Patent Application Publication No. US 2008/0312082 and related applications and patents), event A5547-127 - glufosinate tolerance (U.S. Patent Application Publication No. US 2008/0196127 and related applications and patents), event DAS-40278-9 - tolerance to 2,4- dichlorophenoxyacetic acid and aryloxyphenoxypropionate (see WO 201 1/022469, WO 201 1/022470, WO 201 1/022471 , and related applications and patents), event 127 - ALS tolerance (WO 2010/080829 and related applications and patents), event GTS 40-3-2 - glyphosate tolerance, event DAS-68416-4- 2,4-dichlorophenoxyacetic acid and glufosinate tolerance, event FG72 - glyphosate and isoxaflutole tolerance, event BPS-CV127-9 - ALS tolerance and GU262 - glufosinate tolerance or event SYHT04R - HPPD tolerance.

Under certain circumstances, compounds of Formula (I) according to the present invention when used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizi ) on soy bean plants (in particular any of the transgenic soybean plants as described above), may display a synergistic interaction between the active ingredients.

Additionally, to date, no cross-resistance has been observed between the compounds of Formula (I) (including any one of compounds described in Table 2 (below)) and the current fungicidal solutions used to control Phakopsora pachyrhizi.

Indeed, fungicidal-resistant strains of Phakopsora pachyrhizi have been reported in the scientific literature, with strains resistant to one or more fungicides from at least each of the following fungicidal mode of action classes being observed: sterol demethylation-inhibitors (DMI), quinone-outside-inhibitors (Qol) and succinate dehydrogenase inhibitors (SDHI). See for example: “Sensitivity of Phakopsora pachyrhizi towards quinone-outside-inhibitors and demethylation-inhibitors, and corresponding resistance mechanisms.” Schmitz HK et al, Pest Manag Sci (2014) 70: 378-388;“First detection of a SDH variant with reduced SDHI sensitivity in Phakopsora pachyrhizi’ Simoes K et al, J Plant Dis Prot (2018) 125: 21 -2;“Competitive fitness of Phakopsora pachyrhizi isolates with mutations in the CYP51 and CYTB genes.” Klosowski AC et al, Phytopathology (2016) 106: 1278-1284;“Detection of the F129L mutation in the cytochrome b gene in Phakopsora pachyrhizi." Klosowski AC et al, Pest Manag Sci (2016) 72: 121 1 -1215.

Thus, in a preferred embodiment, the compounds of Formula (I) (including any one of compounds described in Table 2 (below)), or fungicidal compositions according to the present invention comprising a compound of Formula (I), are used to control Phakopsora pachyrhizi which are resistant to one or more fungicides from any of the following fungicidal MoA classes: sterol demethylation-inhibitors (DMI), quinone-outside-inhibitors (Qol) and succinate dehydrogenase inhibitors (SDHI).

The compounds of Formula (I) (including any one of described in Table 2 (below)) or fungicidal compositions according to the present invention comprising a compound of Formula (I) may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizi) on soy bean plants. In particular, there are known in the scientific literature certain Elite soybean plant varieties where R-gene stacks, conferring a degree of immunity or resistance to specific Phakopsora pachyrhizi, have been been introgressed in the plant genome, see for example: “Fighting Asian Soybean Rust, Langenbach C, et al, Front Plant Science 7(797) 2016).

An elite plant is any plant from an elite line, such that an elite plant is a representative plant from an elite variety. Non-limiting examples of elite soybean varieties that are commercially available to farmers or soybean breeders include: AG00802, A0868, AG0902, A1923, AG2403, A2824, A3704, A4324, A5404, AG5903, AG6202 AG0934; AG1435; AG2031 ; AG2035; AG2433; AG2733; AG2933; AG3334; AG3832; AG4135; AG4632; AG4934; AG5831 ; AG6534; and AG7231 (Asgrow Seeds, Des Moines, Iowa, USA); BPR0144RR, BPR 4077NRR and BPR 4390NRR (Bio Plant Research, Camp Point, III., USA); DKB17-51 and DKB37-51 (DeKalb Genetics, DeKalb, III., USA); DP 4546 RR, and DP 7870 RR (Delta & Pine Land Company, Lubbock, Tex., USA); JG 03R501 , JG 32R606C ADD and JG 55R503C (JGL Inc., Greencastle, Ind., USA); NKS 13-K2 (NK Division of Syngenta Seeds, Golden Valley, Minnesota, USA); 90M01 , 91 M30, 92M33, 93M1 1 , 94M30, 95M30, 97B52, P008T22R2; P16T17R2; P22T69R; P25T51 R; P34T07R2; P35T58R; P39T67R; P47T36R; P46T21 R; and P56T03R2 (Pioneer Hi-Bred International, Johnston, Iowa, USA); SG4771 NRR and SG5161 NRR/STS (Soygenetics, LLC, Lafayette, Ind., USA); S00-K5, S1 1 -L2, S28-Y2, S43-B1 , S53-A1 , S76-L9, S78-G6, S0009-M2; S007-Y4; S04-D3; S14-A6; S20-T6; S21 -M7; S26-P3; S28-N6; S30-V6; S35-C3; S36-Y6; S39-C4; S47-K5; S48-D9; S52-Y2; S58-Z4; S67-R6; S73-S8; and S78-G6 (Syngenta Seeds, Henderson, Ky., USA); Richer (Northstar Seed Ltd. Alberta, CA); 14RD62 (Stine Seed Co. la., USA); or Armor 4744 (Armor Seed, LLC, Ar., USA).

Thus, in a further preferred embodiment, the compounds of Formula (I) (including any one of compounds described in Table 2 (below)), or fungicidal compositions according to the present invention comprising a compound of Formula (I), are used to control Phakopsora pachyrhizi, (including fungicidally-resistant strains thereof, as outlined above) on Elite soybean plant varieties where R-gene stacks, conferring a degree of immunity or resistance to specific Phakopsora pachyrhizi, have been been introgressed in the plant genome. Numerous benefits may be expected to ensue from said use, e.g. improved biological activity, an advantageous or broader spectrum of activity (inc. sensitive and resistant strains of Phakopsora pachyrhizi), an increased safety profile, improved crop tolerance, synergistic interactions or potentiating properties, improved onset of action or a longer lasting residual activity, a reduction in the number of applications and/or a reduction in the application rate of the compounds and compositions required for effective control of the phytopathogen ( Phakopsora pachyrhizi), thereby enabling beneficial resistance-management practices, reduced environmental impact and reduced operator exposure.

The term“locus” as used herein means fields in or on which plants are growing, or where seeds of cultivated plants are sown, or where seed will be placed into the soil. It includes soil, seeds, and seedlings, as well as established vegetation.

The term“plants” refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits. The term“plant propagation material” is understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example potatoes. There may be mentioned for example seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants. Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants may be protected before transplantation by a total or partial treatment by immersion. Preferably “plant propagation material” is understood to denote seeds.

Pesticidal agents referred to herein using their common name are known, for example, from "The Pesticide Manual", 15th Ed., British Crop Protection Council 2009.

The compounds of formula (I) may be used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation. To this end, they may be conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g. in polymeric substances. As with the type of the compositions, the methods of application, such as spraying, atomising, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances. The compositions may also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.

Suitable carriers and adjuvants, e.g., for agricultural use, can be solid or liquid and are substances useful in formulation technology, e.g. natural or regenerated mineral substances, 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 normally used in the form of compositions and can be applied to the crop area or plant to be treated, simultaneously or in succession with further compounds. These further compounds can be, e.g., fertilizers or micronutrient donors or other preparations, which influence the growth of plants. They can also be selective herbicides or non-selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation.

The compounds of formula (I) may be used in the form of (fungicidal) compositions for controlling or protecting against phytopathogenic microorganisms, comprising as active ingredient at least one compound of formula (I) or of at least one preferred individual compound as above-defined, in free form or in agrochemically usable salt form, and at least one of the above-mentioned adjuvants.

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

(I)·

The compound of formula (I) may be the sole active ingredient of a composition or it may be admixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator where appropriate. An 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, arsenical fungicides, aryl phenyl ketone fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanilate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiolane fungicides, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine fungicides, organophosphorous fungicides, organotin fungicides, oxathiin fungicides, oxazole fungicides, phenylsulfamide fungicides, polysulfide fungicides, pyrazole fungicides, pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxaline fungicides, strobilurin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides, thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides, and zinc fungicides.

Examples of suitable additional active ingredients also include the following: 3-difluoromethyl-1 - methyl-1 H-pyrazole-4-carboxylic acid (9-dichloromethylene-1 ,2,3,4-tetrahydro-1 ,4-methano- naphthalen-5-yl)-amide, 3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxylic acid methoxy-[1 -methyl-2- (2,4,6-trichlorophenyl)-ethyl]-amide, 1 -methyl-3-difluoromethyl-1 H-pyrazole-4-carboxylic acid (2- dichloromethylene-3-ethyl-1 -methyl-indan-4-yl)-amide (1072957-71 -1), 1 -methyl-3-difluoromethyl-1 H- pyrazole-4-carboxylic acid (4'-methylsulfanyl-biphenyl-2-yl)-amide, 1 -methyl-3-difluoromethyl-4H- pyrazole-4-carboxylic acid [2-(2,4-dichloro-phenyl)-2-methoxy-1 -methyl-ethyl]-amide, (5-Chloro-2,4- dimethyl-pyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone, (5-Bromo-4-chloro-2-methoxy- pyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone, 2-{2-[(E)-3-(2,6-Dichloro-phenyl)-1 - methyl-prop-2-en-(E)-ylideneaminooxymethyl]-phenyl}-2-[(Z)-methoxyimino]-N-methyl-acetamide, 3-[5- (4-Chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine, (E)-N-methyl-2- [2- (2, 5- dimethylphenoxymethyl) phenyl]-2-methoxy-iminoacetamide, 4-bromo-2-cyano-N, N-dimethyl-6- trifluoromethylbenzimidazole-1 -sulphonamide, a-[N-(3-chloro-2, 6-xylyl)-2-methoxyacetamido]-y- butyrolactone, 4-chloro-2-cyano-N, - dimethyl-5-p-tolylimidazole-1 -sulfonamide, N-allyl-4, 5,-dimethyl-2- trimethylsilylthiophene-3-carboxamide, N-(l-cyano-1 ,2-dimethylpropyl)-2-(2,4-dichlorophenoxy) propionamide, N- (2-methoxy-5-pyridyl)-cyclopropane carboxamide, ( +-.)-cis-1 -(4-chlorophenyl)-2-(1 H- 1 ,2,4-triazol-1 -yl)-cycloheptanol, 2-(1 -tert-butyl)-1 -(2-chlorophenyl)-3-(1 ,2,4-triazol-1 -yl)-propan-2-ol, 2',6'-dibromo-2-methyl-4-trifluoromethoxy-4'-trifluoromethyl-1 ,3-thiazole- 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-methylpyrimidin-2- yloxy)-phenoxy]phenyl]-3-methoxyacrylate, methyl (E)-2-[2-[3-(phenyl-sulphonyloxy)phenoxy]phenyl-3- methoxyacrylate, methyl (E)-2-[2-[3-(4-nitrophenoxy)phenoxy]phenyl]-3-methoxyacrylate, methyl (E)-2- [2-phenoxyphenyl]-3-methoxyacrylate, methyl (E)-2-[2-(3,5-dimethyl-benzoyl)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-bromo-pyridin-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)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, methyl (E),(E)-2-[2- (5,6-dimethylpyrazin-2-ylmethyloximinomethyl)phenyl]-3-methoxyacrylate, methyl (E)-2-{2-[6-(6- methylpyridin-2-yloxy)pyrimidin-4-yloxy]phenyl}-3-methoxy-crylate, methyl (E),(E)-2-{ 2-(3- methoxyphenyl)methyloximinomethyl]-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)-methyloximinomethyl]phenyl}-3-methoxyacrylate, methyl (E),(E)-2-{2-[(4-chlorophenyl)- methyloximinomethyl]-phenyl}-3-methoxyacrylate, methyl (E)-2-{2-[6-(2-n-propylphenoxy)-1 ,3,5-triazin- 4-yloxy]phenyl}-3-methoxyacrylate, methyl (E),(E)-2-{2-[(3-nitrophenyl)methyloximinomethyl]phenyl}-3- methoxyacrylate, 3-chloro-7-(2-aza-2,7,7-trimethyl-oct-3-en-5-ine), 2,6-dichloro-N-(4- trifluoromethylbenzyl)-benzamide, 3-iodo-2-propinyl alcohol, 4-chlorophenyl-3-iodopropargyl formal, 3- bromo-2,3-diiodo-2-propenyl ethylcarbamate, 2,3,3-triiodoallyl alcohol, 3-bromo-2,3-diiodo-2-propenyl alcohol, 3-iodo-2-propinyl n-butylcarbamate, 3-iodo-2-propinyl n-hexylcarbamate, 3-iodo-2-propinyl cyclohexyl-carbamate, 3-iodo-2-propinyl phenylcarbamate; phenol derivatives, such as tribromophenol, tetrachlorophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophene, 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, 3,5-dimethyl-tetrahydro-1 ,3,5-thiadiazine-2-thione, N-(2-p- chlorobenzoylethyl)-hexaminium chloride, acibenzolar, acypetacs, alanycarb, albendazole, aldimorph, allicin, allyl alcohol, ametoctradin, amisulbrom, amobam, ampropylfos, anilazine, asomate, aureofungin, azaconazole, azafendin, azithiram, azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentaluron, benthiavalicarb, benthiazole, benzalkonium chloride, benzamacril, benzamorf, benzohydroxamic acid, benzovindiflupyr, berberine, bethoxazin, biloxazol, binapacryl, biphenyl, bitertanol, bithionol, bixafen, blasticidin-S, boscalid, bromothalonil, bromuconazole, bupirimate, buthiobate, butylamine calcium polysulfide, captafol, captan, carbamorph, carbendazim, carbendazim chlorhydrate, carboxin, carpropamid, carvone, CGA41396, CGA41397, chinomethionate, chitosan, chlobenthiazone, chloraniformethan, chloranil, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlorozolinate, chlozolinate, climbazole, clotrimazole, clozylacon, copper containing compounds such as copper acetate, copper carbonate, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper oxyquinolate, copper silicate, copper sulphate, copper tallate, copper zinc chromate and Bordeaux mixture, cresol, cufraneb, cuprobam, cuprous oxide, cyazofamid, cyclafuramid, cycloheximide, cyflufenamid, cymoxanil, cypendazole, cyproconazole, cyprodinil, dazomet, debacarb, decafentin, dehydroacetic acid, di-2-pyridyl disulphide 1 , 1 '-dioxide, dichlofluanid, diclomezine, dichlone, dicloran, dichlorophen, dichlozoline, diclobutrazol, diclocymet, diethofencarb, difenoconazole, difenzoquat, diflumetorim, O-di-iso-propyl-S-benzyl thiophosphate, dimefluazole, dimetachlone, dimetconazole, dimethomorph, dimethirimol, diniconazole, diniconazole-M, dinobuton, dinocap, dinocton, dinopenton, dinosulfon, dinoterbon, diphenylamine, dipyrithione, disulfiram, ditalimfos, dithianon, dithioether, dodecyl dimethyl ammonium chloride, dodemorph, dodicin, dodine, doguadine, drazoxolon, edifenphos, enestroburin, epoxiconazole, etaconazole, etem, ethaboxam, ethirimol, ethoxyquin, ethilicin, ethyl (Z)-N-benzyl-N ([methyl (methyl-thioethylideneamino- oxycarbonyl) amino] thio)-B-alaninate, etridiazole, famoxadone, fenamidone, fenaminosulf, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan, fenoxanil, fenpiclonil, fenpicoxamid, fenpropidin, fenpropimorph, fenpyrazamine, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, flumorph, flupicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutanil, flutolanil, flutriafol, fluxapyroxad, folpet, formaldehyde, fosetyl, fuberidazole, furalaxyl, furametpyr, furcarbanil, furconazole, furfural, furmecyclox, furophanate, glyodin, griseofulvin, guazatine, halacrinate, hexachlorobenzene, hexachlorobutadiene, hexachlorophene, hexaconazole, hexylthiofos, hydrargaphen, hydroxyisoxazole, hymexazole, imazalil, imazalil sulphate, imibenconazole, iminoctadine, iminoctadine triacetate, inezin, iodocarb, ipconazole, ipfentrifluconazole, iprobenfos, iprodione, iprovalicarb, isopropanyl butyl carbamate, isoprothiolane, isopyrazam, isotianil, isovaledione, izopamfos, kasugamycin, kresoxim-methyl, LY186054, LY21 1795, LY248908, mancozeb, mandipropamid, maneb, mebenil, mecarbinzid, mefenoxam, mefentrifluconazole, mepanipyrim, mepronil, mercuric chloride, mercurous chloride, meptyldinocap, metalaxyl, metalaxyl-M, metam, metazoxolon, metconazole, methasulfocarb, methfuroxam, methyl bromide, methyl iodide, methyl isothiocyanate, metiram, metiram-zinc, metominostrobin, metrafenone, metsulfovax, milneb, moroxydine, myclobutanil, myclozolin, nabam, natamycin, neoasozin, nickel dimethyldithiocarbamate, nitrostyrene, nitrothal-iso-propyl, nuarimol, octhilinone, ofurace, organomercury compounds, orysastrobin, osthol, oxadixyl, oxasulfuron, oxathiapiprolin, oxine-copper, oxolinic acid, oxpoconazole, oxycarboxin, parinol, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, penthiopyrad, phenamacril, phenazin oxide, phosdiphen, phosetyl-AI, phosphorus acids, phthalide, picoxystrobin, piperalin, polycarbamate, polyoxin D, polyoxrim, polyram, probenazole, prochloraz, procymidone, propamidine, propamocarb, propiconazole, propineb, propionic acid, proquinazid, prothiocarb, prothioconazole, pydiflumetofen, pyracarbolid, pyraclostrobin, pyrametrostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyridinitril, pyrifenox, pyrimethanil, pyriofenone, pyroquilon, pyroxychlor, pyroxyfur, pyrrolnitrin, quaternary ammonium compounds, quinacetol, quinazamid, quinconazole, quinomethionate, quinoxyfen, quintozene, rabenzazole, santonin, sedaxane, silthiofam, simeconazole, sipconazole, sodium pentachlorophenate, spiroxamine, streptomycin, sulphur, sultropen, tebuconazole, tebfloquin, tecloftalam, tecnazene, tecoram, tetraconazole, thiabendazole, thiadifluor, thicyofen, thifluzamide, 2-(thiocyanomethylthio) benzothiazole, thiophanate-methyl, thioquinox, thiram, tiadinil, timibenconazole, tioxymid, tolclofos- methyl, tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol, triazbutil, triazoxide, tricyclazole, tridemorph, trifloxystrobin, triflumazole, triforine, triflumizole, triticonazole, uniconazole, urbacide, validamycin, valifenalate, vapam, vinclozolin, zarilamid, zineb, ziram, and zoxamide.

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

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

The compounds of the invention may be used in combination with derivatives and analogues of the general class of dioxomorpholine antiparasitic agents as described in WO-9615121 and also with anthelmintic active cyclic depsipeptides such as those described in WO-961 1945, WO-9319053, WO- 9325543, EP-626375, EP-382173, WO-9419334, EP-382173, and EP-503538.

The compounds of the invention may be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; 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 invention may be used in combination with terpene alkaloids, for example those described in WO 95/19363 or WO 04/72086, particularly the compounds disclosed therein.

Other examples of such biologically active compounds that the compounds of the invention may be used in combination with include but are not restricted to the following:

Organophosphates: acephate, azamethiphos, azinphos-ethyl, azinphos- methyl, bromophos, bromophos-ethyl, cadusafos, chlorethoxyphos, chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton-S-methyl, demeton-S-methyl sulphone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosthiazate, heptenophos, isazophos, isothioate, isoxathion, malathion, methacriphos, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, paraoxon, parathion, parathion-methyl, phenthoate, phosalone, phosfolan, phosphocarb, phosmet, phosphamidon, phorate, phoxim, pirimiphos, pirimiphos-methyl, profenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, sulprophos, temephos, terbufos, tebupirimfos, tetrachlorvinphos, thimeton, triazophos, trichlorfon, vamidothion. Carbamates: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801 , isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, UC-51717.

Pyrethroids: acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl (E)-(1 R)-cis-2,2- dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bifenthrin, beta-cyfluthrin, cyfluthrin, a-cypermethrin, beta-cypermethrin, bioallethrin, bioallethrin((S)-cyclopentylisomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, ethofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), imiprothrin, cyhalothrin, lambda-cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrins (natural products), resmethrin, tetramethrin, transfluthrin, theta-cypermethrin, silafluofen, t- fluvalinate, tefluthrin, tralomethrin, Zeta-cypermethrin.

Arthropod growth regulators: a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, chlorfentazine; 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-1 18, azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl, bromopropylate, BTG-504, BTG-505, camphechlor, cartap, chlorobenzilate, chlordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine, diacloden, diafenthiuron, DBI-3204, dinactin, dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan, ethiprole, ethofenprox, fenazaquin, flumite, MTI- 800, fenpyroximate, fluacrypyrim, flubenzimine, flubrocythrinate, flufenzine, flufenprox, fluproxyfen, halofenprox, hydramethylnon, IKI-220, kanemite, NC-196, neem guard, nidinorterfuran, nitenpyram, SD-35651 , WL-108477, pirydaryl, propargite, protrifenbute, pymethrozine, pyridaben, pyrimidifen, NC-1 1 1 1 , R-195,RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601 , silafluofen, silomadine, spinosad, tebufenpyrad, tetradifon, tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad, triazamate, triethoxyspinosyn, trinactin, verbutin, vertalec, YI-5301 .

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

Bactericides: chlortetracycline, oxytetracycline, streptomycin.

Other biological agents: enrofloxacin, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel, triclabendazole.

Another aspect of invention is related to the use of a compound of formula (I) or of a preferred individual compound as above-defined, of a composition comprising at least one compound of formula (I) or at least one preferred individual compound as above-defined, or of a fungicidal or insecticidal mixture comprising at least one compound of formula (I) or at least one preferred individual compound as above-defined, in admixture with other fungicides or insecticides as described above, for controlling or preventing infestation of plants, e.g. useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g., harvested food crops, or non-living materials by insects or by phytopathogenic microorganisms, preferably fungal organisms.

A further aspect of invention is related to a method of controlling or preventing an infestation of plants, e.g., useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. harvested food crops, or of non-living materials by insects or by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, which comprises the application of a compound of formula (I) or of a preferred individual compound as above-defined as active ingredient to the plants, to parts of the plants or to the locus thereof, to the propagation material thereof, or to any part of the non-living materials.

Controlling or preventing means reducing infestation by insects or by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, to such a level that an improvement is demonstrated.

A preferred method of controlling or preventing an infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects which comprises the application of a compound of formula (I), or an agrochemical composition which contains at least one of said compounds, is foliar application. The frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen or insect. However, the compounds of formula (I) can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plant with a liquid formulation, or by applying the compounds in solid form to the soil, e.g., in granular form (soil application). In crops of water rice such granulates can be applied to the flooded rice field. The compounds of formula (I) may also be applied to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation.

A formulation, e.g. a composition containing the compound of formula (I), and, if desired, a solid or liquid adjuvant or monomers for encapsulating the compound of formula (I), may be prepared in a known manner, typically by intimately mixing and/or grinding the compound with extenders, for example solvents, solid carriers and, optionally, surface active compounds (surfactants).

Advantageous rates of application are normally from 5g to 2kg of active ingredient (a.i.) per hectare (ha), preferably from 10g to 1 kg a.i./ha, most preferably from 20g to 600g a.i./ha. When used as seed drenching agent, convenient dosages are from 10mg to 1 g of active substance per kg of seeds.

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

The following mixtures of the compounds of formula (I) with active ingredients are preferred. The abbreviation“TX” means one compound selected from the group of compounds 1 .a.001 - 1 .a.100 to 1 .bf.001 - 1 .bf.100 described in Table 1 , and the compounds described in Table 2 (below): a compound selected from the group of substances consisting of petroleum oils + TX, 1 ,1 -bis(4- chlorophenyl)-2-ethoxyethanol + TX, 2,4-dichlorophenyl benzenesulfonate + TX, 2-fluoro-N-methyl-N- 1 -naphthylacetamide + TX, 4-chlorophenyl phenyl sulfone + TX, acetoprole + TX, aldoxycarb + TX, amidithion + TX, amidothioate + TX, amiton + TX, amiton hydrogen oxalate + TX, amitraz + TX, aramite + TX, arsenous oxide + TX, azobenzene + TX, azothoate + TX, benomyl + TX, benoxafos + TX, benzyl benzoate + TX, bixafen + TX, brofenvalerate + TX, bromocyclen + TX, bromophos + TX, bromopropylate + TX, buprofezin + TX, butocarboxim + TX, butoxycarboxim + TX, butylpyridaben + TX, calcium polysulfide + TX, camphechlor + TX, carbanolate + TX, carbophenothion + TX, cymiazole + TX, chino- methionat + TX, chlorbenside + TX, chlordimeform + TX, chlordimeform hydrochloride + TX, chlorfenethol + TX, chlorfenson + TX, chlorfensulfide + TX, chlorobenzilate + TX, chloromebuform + TX, chloromethiuron + TX, chloropropylate + TX, chlorthiophos + TX, cinerin I + TX, cinerin II + TX, cinerins + TX, closantel + TX, coumaphos + TX, crotamiton + TX, crotoxyphos + TX, cufraneb + TX, cyanthoate + TX, DCPM + TX, DDT + TX, demephion + TX, demephion-O + TX, demephion-S + TX, demeton- methyl + TX, demeton-O + TX, demeton-O-methyl + TX, demeton-S + TX, demeton-S-methyl + TX, demeton-S-methylsulfon + TX, dichlofluanid + TX, dichlorvos + TX, dicliphos + TX, dienochlor + TX, dimefox + TX, dinex + TX, dinex-diclexine + TX, dinocap-4 + TX, dinocap-6 + TX, dinocton + TX, dino- penton + TX, dinosulfon + TX, dinoterbon + TX, dioxathion + TX, diphenyl sulfone + TX, disulfiram + TX, DNOC + TX, dofenapyn + TX, doramectin + TX, endothion + TX, eprinomectin + TX, ethoate-methyl + TX, etrimfos + TX, fenazaflor + TX, fenbutatin oxide + TX, fenothiocarb + TX, fenpyrad + TX, fen- pyroximate + TX, fenpyrazamine + TX, fenson + TX, fentrifanil + TX, flubenzimine + TX, flucycloxuron + TX, fluenetil + TX, fluorbenside + TX, FMC 1 137 + TX, formetanate + TX, formetanate hydrochloride + TX, formparanate + TX, gamma-HCH + TX, glyodin + TX, halfenprox + TX, hexadecyl cyclopropanecarboxylate + TX, isocarbophos + TX, jasmolin I + TX, jasmolin II + TX, jodfenphos + TX, lindane + TX, malonoben + TX, mecarbam + TX, mephosfolan + TX, mesulfen + TX, methacrifos + TX, methyl bromide + TX, metolcarb + TX, mexacarbate + TX, milbemycin oxime + TX, mipafox + TX, monocrotophos + TX, morphothion + TX, moxidectin + TX, naled + TX, 4-chloro-2-(2-chloro-2-methyl- propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one + TX, nifluridide + TX, nikkomycins + TX, nitrilacarb + TX, nitrilacarb 1 :1 zinc chloride complex + TX, omethoate + TX, oxydeprofos + TX, oxydisulfoton + TX, pp'-DDT + TX, parathion + TX, permethrin + TX, phenkapton + TX, phosalone + TX, phosfolan + TX, phosphamidon + TX, polychloroterpenes + TX, polynactins + TX, proclonol + TX, promacyl + TX, propoxur + TX, prothidathion + TX, prothoate + TX, pyrethrin I + TX, pyrethrin II + TX, pyrethrins + TX, pyridaphenthion + TX, pyrimitate + TX, quinalphos + TX, quintiofos + TX, R-1492 + TX, phosglycin + TX, rotenone + TX, schradan + TX, sebufos + TX, selamectin + TX, sophamide + TX, SSI- 121 + TX, sulfiram + TX, sulfluramid + TX, sulfotep + TX, sulfur + TX, diflovidazin + TX, tau-fluvalinate + TX, TEPP + TX, terbam + TX, tetradifon + TX, tetrasul + TX, thiafenox + TX, thiocarboxime + TX, thiofanox + TX, thiometon + TX, thioquinox + TX, thuringiensin + TX, triamiphos + TX, triarathene + TX, triazophos + TX, triazuron + TX, trifenofos + TX, trinactin + TX, vamidothion + TX, vaniliprole + TX, bethoxazin + TX, copper dioctanoate + TX, copper sulfate + TX, cybutryne + TX, dichlone + TX, dichlorophen + TX, endothal + TX, fentin + TX, hydrated lime + TX, nabam + TX, quinoclamine + TX, quinonamid + TX, simazine + TX, triphenyltin acetate + TX, triphenyltin hydroxide + TX, crufomate + TX, piperazine + TX, thiophanate + TX, chloralose + TX, fenthion + TX, pyridin-4-amine + TX, strychnine + TX, 1 -hydroxy-1 H-pyridine-2-thione + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide + TX, 8- hydroxyquinoline sulfate + TX, bronopol + TX, copper hydroxide + TX, cresol + TX, dipyrithione + TX, dodicin + TX, fenaminosulf + TX, formaldehyde + TX, hydrargaphen + TX, kasugamycin + TX, kasugamycin hydrochloride hydrate + TX, nickel bis(dimethyldithiocarbamate) + TX, nitrapyrin + TX, octhilinone + TX, oxolinic acid + TX, oxytetracycline + TX, potassium hydroxyquinoline sulfate + TX, probenazole + TX, streptomycin + TX, streptomycin sesquisulfate + TX, tecloftalam + TX, thiomersal + TX, Adoxophyes orana GV + TX, Agrobacterium radiobacter + TX, Amblyseius spp. + TX, Anagrapha falcifera NPV + TX, Anagrus atomus + TX, Aphelinus abdominalis + TX, Aphidius colemani + TX, Aphidoletes aphidimyza + TX, Autographa californica NPV + TX, Bacillus sphaericus Neide + TX, Beauveria brongniartii + TX, Chrysoperla carnea + TX, Cryptolaemus montrouzieri + TX, Cydia pomonella GV + TX, Dacnusa sibirica + TX, Diglyphus isaea + TX, Encarsia formosa + TX, Eretmocerus eremicus + TX, Heterorhabditis bacteriophora and H. megidis + TX, Hippodamia convergens + TX, Leptomastix dactylopii + TX, Macrolophus caliginosus + TX, Mamestra brassicae NPV + TX, Metaphycus helvolus + TX, Metarhizium anisopliae var. acridum + TX, Metarhizium anisopliae var. anisopliae + TX, Neodiprion sertifer NPV and N. lecontei NPV + TX, Orius spp. + TX, Paecilomyces fumosoroseus + TX, Phytoseiulus persimilis + TX, Steinernema bibionis + TX, Steinernema carpocapsae + TX, Steinernema feltiae + TX, Steinernema glaseri + TX, Steinernema riobrave + TX, Steinernema riobravis + TX, Steinernema scapterisci + TX, Steinernema spp. + TX, Trichogramma spp. + TX, Typhlodromus occidentalis + TX , Verticillium lecanii + TX, apholate + TX, bisazir + TX, busulfan + TX, dimatif + TX, hemel + TX, hempa + TX, metepa + TX, methiotepa + TX, methyl apholate + TX, morzid + TX, penfluron + TX, tepa + TX, thiohempa + TX, thiotepa + TX, tretamine + TX, uredepa + TX, (E)-dec-5-en-1 -yl acetate with (E)-dec-5-en-1 -ol + TX, (E)-tridec-4-en-1 -yl acetate + TX, (E)-6- methylhept-2-en-4-ol + TX, (E,Z)-tetradeca-4,10-dien-1 -yl acetate + TX, (Z)-dodec-7-en-1 -yl acetate + TX, (Z)-hexadec-1 1 -enal + TX, (Z)-hexadec-l 1 -en-1 -yl acetate + TX, (Z)-hexadec-13-en-1 1 -yn-1 -yl acetate + TX, (Z)-icos-13-en-10-one + TX, (Z)-tetradec-7-en-1 -al + TX, (Z)-tetradec-9-en-1 -ol + TX, (Z)- tetradec-9-en-1 -yl acetate + TX, (7E,9Z)-dodeca-7,9-dien-1 -yl acetate + TX, (9Z,1 1 E)-tetradeca-9,1 1 - dien-1 -yl acetate + TX, (9Z,12E)-tetradeca-9,12-dien-1 -yl acetate + TX, 14-methyloctadec-1 -ene + TX, 4-methylnonan-5-ol with 4-methylnonan-5-one + TX, alpha-multistriatin + TX, brevicomin + TX, codlelure + TX, codlemone + TX, cuelure + TX, disparlure + TX, dodec-8-en-1 -yl acetate + TX, dodec-9-en-1 -yl acetate + TX, dodeca-8 + TX, 10-dien-1 -yl acetate + TX, dominicalure + TX, ethyl 4-methyloctanoate + TX, eugenol + TX, frontalin + TX, grandlure + TX, grandlure I + TX, grandlure II + TX, grandlure III + TX, grandlure IV + TX, hexalure + TX, ipsdienol + TX, ipsenol + TX, japonilure + TX, lineatin + TX, litlure + TX, looplure + TX, medlure + TX, megatomoic acid + TX, methyl eugenol + TX, muscalure + TX, octadeca-2,13-dien-1 -yl acetate + TX, octadeca-3,13-dien-1 -yl acetate + TX, orfralure + TX, oryctalure + TX, ostramone + TX, siglure + TX, sordidin + TX, sulcatol + TX, tetradec-1 1 -en-1 -yl acetate + TX, trimedlure + TX, trimedlure A + TX, trimedlure Bi + TX, trimedlure B2 + TX, trimedlure C + TX, trunc-call + TX, 2-(octylthio)ethanol + TX, butopyronoxyl + TX, butoxy(polypropylene glycol) + TX, dibutyl adipate + TX, dibutyl phthalate + TX, dibutyl succinate + TX, diethyltoluamide + TX, dimethyl carbate + TX, dimethyl phthalate + TX, ethyl hexanediol + TX, hexamide + TX, methoquin-butyl + TX, methylneodecanamide + TX, oxamate + TX, picaridin + TX, 1 -dichloro-1 -nitroethane + TX, 1 ,1 -dichloro- 2,2-bis(4-ethylphenyl)ethane + TX, 1 ,2-dichloropropane with 1 ,3-dichloropropene + TX, 1 -bromo-2- chloroethane + TX, 2,2,2-trichloro-1 -(3,4-dichlorophenyl)ethyl acetate + TX, 2,2-dichlorovinyl 2- ethylsulfinylethyl methyl phosphate + TX, 2-(1 ,3-dithiolan-2-yl)phenyl dimethylcarbamate + TX, 2-(2- butoxyethoxy)ethyl thiocyanate + TX, 2-(4,5-dimethyl-1 ,3-dioxolan-2-yl)phenyl methylcarbamate + TX, 2-(4-chloro-3,5-xylyloxy)ethanol + TX, 2-chlorovinyl diethyl phosphate + TX, 2-imidazolidone + TX, 2- isovalerylindan-1 ,3-dione + TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate + TX, 2- thiocyanatoethyl laurate + TX, 3-bromo-1 -chloroprop-1 -ene + TX, 3-methyl-1 -phenylpyrazol-5-yl dimethylcarbamate + TX, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate + TX, 5,5-dimethyl-3- oxocyclohex-1 -enyl dimethylcarbamate + TX, acethion + TX, acrylonitrile + TX, aldrin + TX, allosamidin + TX, allyxycarb + TX, alpha-ecdysone + TX, aluminium phosphide + TX, aminocarb + TX, anabasine + TX, athidathion + TX, azamethiphos + TX, Bacillus thuringiensis delta endotoxins + TX, barium hexafluorosilicate + TX, barium polysulfide + TX, barthrin + TX, Bayer 22/190 + TX, Bayer 22408 + TX, beta-cyfluthrin + TX, beta-cypermethrin + TX, bioethanomethrin + TX, biopermethrin + TX, bis(2- chloroethyl) ether + TX, borax + TX, bromfenvinfos + TX, bromo-DDT + TX, bufencarb + TX, butacarb + TX, butathiofos + TX, butonate + TX, calcium arsenate + TX, calcium cyanide + TX, carbon disulfide + TX, carbon tetrachloride + TX, cartap hydrochloride + TX, cevadine + TX, chlorbicyclen + TX, chlordane + TX, chlordecone + TX, chloroform + TX, chloropicrin + TX, chlorphoxim + TX, chlorprazophos + TX, cis-resmethrin + TX, cismethrin + TX, clocythrin + TX, copper acetoarsenite + TX, copper arsenate + TX, copper oleate + TX, coumithoate + TX, cryolite + TX, CS 708 + TX, cyanofenphos + TX, cyanophos + TX, cyclethrin + TX, cythioate + TX, d-tetramethrin + TX, DAEP + TX, dazomet + TX, decarbofuran + TX, diamidafos + TX, dicapthon + TX, dichlofenthion + TX, dicresyl + TX, dicyclanil + TX, dieldrin + TX, diethyl 5-methylpyrazol-3-yl phosphate + TX, dilor + TX, dimefluthrin + TX, dimetan + TX, dimethrin + TX, dimethylvinphos + TX, dimetilan + TX, dinoprop + TX, dinosam + TX, dinoseb + TX, diofenolan + TX, dioxabenzofos + TX, dithicrofos + TX, DSP + TX, ecdysterone + TX, El 1642 + TX, EMPC + TX, EPBP + TX, etaphos + TX, ethiofencarb + TX, ethyl formate + TX, ethylene dibromide + TX, ethylene dichloride + TX, ethylene oxide + TX, EXD + TX, fenchlorphos + TX, fenethacarb + TX, fenitrothion + TX, fenoxacrim + TX, fenpirithrin + TX, fensulfothion + TX, fenthion-ethyl + TX, flucofuron + TX, fosmethilan + TX, fospirate + TX, fosthietan + TX, furathiocarb + TX, furethrin + TX, guazatine + TX, guazatine acetates + TX, sodium tetrathiocarbonate + TX, halfenprox + TX, HCH + TX, HEOD + TX, heptachlor + TX, heterophos + TX, HHDN + TX, hydrogen cyanide + TX, hyquincarb + TX, IPSP + TX, isazofos + TX, isobenzan + TX, isodrin + TX, isofenphos + TX, isolane + TX, isoprothiolane + TX, isoxathion + TX, juvenile hormone I + TX, juvenile hormone II + TX, juvenile hormone III + TX, kelevan + TX, kinoprene + TX, lead arsenate + TX, leptophos + TX, lirimfos + TX, lythidathion + TX, m-cumenyl methylcarbamate + TX, magnesium phosphide + TX, mazidox + TX, mecarphon + TX, menazon + TX, mercurous chloride + TX, mesulfenfos + TX, metam + TX, metam-potassium + TX, metam-sodium + TX, methanesulfonyl fluoride + TX, methocrotophos + TX, methoprene + TX, methothrin + TX, methoxychlor + TX, methyl isothiocyanate + TX, methylchloroform + TX, methylene chloride + TX, metoxadiazone + TX, mirex + TX, naftalofos + TX, naphthalene + TX, NC-170 + TX, nicotine + TX, nicotine sulfate + TX, nithiazine + TX, nornicotine + TX, 0-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate + TX, O,O-diethyl 0-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate + TX, O,O-diethyl 0-6-methyl-2-propylpyrimidin-4-yl phosphorothioate + TX, O,O,O',O'-tetrapropyl dithiopyrophosphate + TX, oleic acid + TX, para-dichlorobenzene + TX, parathion-methyl + TX, pentachlorophenol + TX, pentachlorophenyl laurate + TX, PH 60-38 + TX, phenkapton + TX, phosnichlor + TX, phosphine + TX, phoxim-methyl + TX, pirimetaphos + TX, polychlorodicyclopentadiene isomers + TX, potassium arsenite + TX, potassium thiocyanate + TX, precocene I + TX, precocene II + TX, precocene III + TX, primidophos + TX, profluthrin + TX, promecarb + TX, prothiofos + TX, pyrazophos + TX, pyresmethrin + TX, quassia + TX, quinalphos-methyl + TX, quinothion + TX, rafoxanide + TX, resmethrin + TX, rotenone + TX, kadethrin + TX, ryania + TX, ryanodine + TX, sabadilla) + TX, schradan + TX, sebufos + TX, SI-0009 + TX, thiapronil + TX, sodium arsenite + TX, sodium cyanide + TX, sodium fluoride + TX, sodium hexafluorosilicate + TX, sodium pentachlorophenoxide + TX, sodium selenate + TX, sodium thiocyanate + TX, sulcofuron + TX, sulcofuron-sodium + TX, sulfuryl fluoride + TX, sulprofos + TX, tar oils + TX, tazimcarb + TX, TDE + TX, tebupirimfos + TX, temephos + TX, terallethrin + TX, tetrachloroethane + TX, thicrofos + TX, thiocyclam + TX, thiocyclam hydrogen oxalate + TX, thionazin + TX, thiosultap + TX, thiosultap-sodium + TX, tralomethrin + TX, transpermethrin + TX, triazamate + TX, trichlormetaphos-3 + TX, trichloronat + TX, trimethacarb + TX, tolprocarb + TX, triclopyricarb + TX, triprene + TX, veratridine + TX, veratrine + TX, XMC + TX, zetamethrin + TX, zinc phosphide + TX, zolaprofos + TX, meperfluthrin + TX, tetramethylfluthrin + TX, bis(tributyltin) oxide + TX, bromoacetamide + TX, ferric phosphate + TX, niclosamide-olamine + TX, tributyltin oxide + TX, pyrimorph + TX, trifenmorph + TX, 1 ,2-dibromo-3-chloropropane + TX, 1 ,3-dichloropropene + TX, 3,4- dichlorotetrahydrothiophene 1 ,1 -dioxide + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 5-methyl-6- thioxo-1 ,3,5-thiadiazinan-3-ylacetic acid + TX, 6-isopentenylaminopurine + TX, 2-fluoro-N-(3- methoxyphenyl)-9H-purin-6-amine + TX, benclothiaz + TX, cytokinins + TX, DCIP + TX, furfural + TX, isamidofos + TX, kinetin + TX, Myrothecium verrucaria composition + TX, tetrachlorothiophene + TX, xylenols + TX, zeatin + TX, potassium ethylxanthate + TX .acibenzolar + TX, acibenzolar-S-methyl + TX, Reynoutria sachalinensis extract + TX, alpha-chlorohydrin + TX, antu + TX, barium carbonate + TX, bisthiosemi + TX, brodifacoum + TX, bromadiolone + TX, bromethalin + TX, chlorophacinone + TX, cholecalciferol + TX, coumachlor + TX, coumafuryl + TX, coumatetralyl + TX, crimidine + TX, difenacoum + TX, difethialone + TX, diphacinone + TX, ergocalciferol + TX, flocoumafen + TX, fluoroacetamide + TX, flupropadine + TX, flupropadine hydrochloride + TX, norbormide + TX, phosacetim + TX, phosphorus + TX, pindone + TX, pyrinuron + TX, scilliroside + TX, sodium fluoroacetate + TX, thallium sulfate + TX, warfarin + TX, 2-(2-butoxyethoxy)ethyl piperonylate + TX, 5-(1 ,3-benzodioxol-5-yl)-3- hexylcyclohex-2-enone + TX, farnesol with nerolidol + TX, verbutin + TX, MGK 264 + TX, piperonyl butoxide + TX, piprotal + TX, propyl isomer + TX, S421 + TX, sesamex + TX, sesasmolin + TX, sulfoxide + TX, anthraquinone + TX, copper naphthenate + TX, copper oxychloride + TX, dicyclopentadiene + TX, thiram + TX, zinc naphthenate + TX, ziram + TX, imanin + TX, ribavirin + TX, mercuric oxide + TX, thiophanate-methyl + TX, azaconazole + TX, bitertanol + TX, bromuconazole + TX, cyproconazole + TX, difenoconazole + TX, diniconazole + TX, epoxiconazole + TX, fenbuconazole + TX, fluquinconazole + TX, flusilazole + TX, flutriafol + TX, furametpyr + TX, hexaconazole + TX, imazalil + TX, imiben- conazole + TX, ipconazole + TX, metconazole + TX, myclobutanil + TX, paclobutrazole + TX, pefurazoate + TX, penconazole + TX, prothioconazole + TX, pyrifenox + TX, prochloraz + TX, propiconazole + TX, pyrisoxazole + TX, simeconazole + TX, tebuconazole + TX, tetraconazole + TX, triadimefon + TX, triadimenol + TX, triflumizole + TX, triticonazole + TX, ancymidol + TX, fenarimol + TX, nuarimol + TX, bupirimate + TX, dimethirimol + TX, ethirimol + TX, dodemorph + TX, fenpropidine + TX, fenpropimorph + TX, spiroxamine + TX, tridemorph + TX, cyprodinil + TX, mepanipyrim + TX, pyrimethanil + TX, fenpiclonil + TX, fludioxonil + TX, benalaxyl + TX, furalaxyl + TX, metalaxyl -+ TX, Rmetalaxyl + TX, ofurace + TX, oxadixyl + TX, carbendazim + TX, debacarb + TX, fuberidazole + TX, thiabendazole + TX, chlozolinate + TX, dichlozoline + TX, myclozoline + TX, procymidone + TX, vinclozoline + TX, boscalid + TX, carboxin + TX, fenfuram + TX, flutolanil + TX, mepronil + TX, oxycarboxin + TX, penthiopyrad + TX, thifluzamide + TX, dodine + TX, iminoctadine + TX, azoxystrobin + TX, dimoxystrobin + TX, enestroburin + TX, fenaminstrobin + TX, flufenoxystrobin + TX, fluoxastrobin + TX, kresoxim-methyl + TX, metominostrobin + TX, trifloxystrobin + TX, orysastrobin + TX, picoxystrobin + TX, pyraclostrobin + TX, pyrametostrobin + TX, pyraoxystrobin + TX, ferbam + TX, mancozeb + TX, maneb + TX, metiram + TX, propineb + TX, zineb + TX, captafol + TX, captan + TX, fluoroimide + TX, folpet + TX, tolylfluanid + TX, bordeaux mixture + TX, copper oxide + TX, mancopper + TX, oxine-copper + TX, nitrothal-isopropyl + TX, edifenphos + TX, iprobenphos + TX, phosdiphen + TX, tolclofos-methyl + TX, anilazine + TX, benthiavalicarb + TX, blasticidin-S + TX, chloroneb + TX, chlorothalonil + TX, cyflufenamid + TX, cymoxanil + TX, cyclobutrifluram + TX, diclocymet + TX, diclomezine + TX, dicloran + TX, diethofencarb + TX, dimethomorph + TX, flumorph + TX, dithianon + TX, ethaboxam + TX, etridiazole + TX, famoxadone + TX, fenamidone + TX, fenoxanil + TX, ferimzone + TX, fluazinam + TX, fluopicolide + TX, flusulfamide + TX, fluxapyroxad + TX, fenhexamid + TX, fosetyl- aluminium + TX, hymexazol + TX, iprovalicarb + TX, cyazofamid + TX, methasulfocarb + TX, metrafenone + TX, pencycuron + TX, phthalide + TX, polyoxins + TX, propamocarb + TX, pyribencarb + TX, proquinazid + TX, pyroquilon + TX, pyriofenone + TX, quinoxyfen + TX, quintozene + TX, tiadinil + TX, triazoxide + TX, tricyclazole + TX, triforine + TX, validamycin + TX, valifenalate + TX, zoxamide + TX, mandipropamid + TX, flubeneteram + TX, isopyrazam + TX, sedaxane + TX, benzovindiflupyr + TX, pydiflumetofen + TX, 3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro- biphenyl-2-yl)-amide + TX, isoflucypram + TX, isotianil + TX, dipymetitrone + TX, 6-ethyl-5,7-dioxo- pyrrolo[4,5][1 ,4]dithiino[1 ,2-c]isothiazole-3-carbonitrile + TX, 2-(difluoromethyl)-N-[3-ethyl-1 ,1 -dimethyl- indan-4-yl]pyridine-3-carboxamide + TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3- carbonitrile + TX, (R)-3-(difluoromethyl)-1 -methyl-N-[1 ,1 ,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine + TX, 4- (2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1 ,3-dimethyl-1 H-pyrazol-5-amine + TX, fluindapyr + TX, coumethoxystrobin (jiaxiangjunzhi) + TX, Ivbenmixianan + TX, dichlobentiazox + TX, mandestrobin + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1 -yl)quinolone + TX, 2-[2-fluoro- 6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol + TX, oxathiapiprolin + TX, tert-butyl N-[6-[[[(1 - methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, pyraziflumid + TX, inpyrfluxam + TX, trolprocarb + TX, mefentrifluconazole + TX, ipfentrifluconazole+ TX, 2- (difluoromethyl)-N-[(3R)-3-ethyl-1 ,1 -dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, N'-(2,5-dimethyl- 4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5- dimethyl-phenyl]-N-ethyl-N-methyl-formamidine + TX, [2-[3-[2-[1 -[2-[3,5-bis(difluoromethyl)pyrazol-1 - yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl] methanesulfonate + TX, but-3-ynyl N-[6-[[(Z)-[(1 -methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate + TX, 3-chloro- 6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX, pyridachlometyl + TX, 3-(difluoromethyl)-1 - methyl-N-[1 ,1 ,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 1 -[2-[[1 -(4-chlorophenyl)pyrazol-3- yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one + TX, 1 -methyl-4-[3-methyl-2-[[2-methyl-4- (3,4,5-trimethylpyrazol-1 -yl)phenoxy]methyl]phenyl]tetrazol-5-one + TX, aminopyrifen + TX, ametoctradin + TX, amisulbrom + TX, penflufen + TX, (Z,2E)-5-[1 -(4-chlorophenyl)pyrazol-3-yl]oxy-2- methoxyimino-N,3-dimethyl-pent-3-enamide + TX, florylpicoxamid + TX, fenpicoxamid + TX, tebufloquin + TX, ipflufenoquin + TX, quinofumelin + TX, isofetamid + TX, N-[2-[2,4-dichloro-phenoxy]phenyl]-3- (difluoromethyl)-1 -methyl-pyrazole-4-carboxamide + TX, N-[2-[2-chloro-4-

(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1 -methyl-pyrazole-4-carboxamide + TX, benzothiostrobin + TX, phenamacril + TX, 5-amino-1 ,3,4-thiadiazole-2-thiol zinc salt (2:1) + TX, fluopyram + TX, flutianil + TX, fluopimomide + TX, pyrapropoyne + TX, picarbutrazox + TX, 2- (difluoromethyl)-N-(3-ethyl-1 ,1 -dimethyl-indan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N- ((3R)-1 ,1 ,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, 4-[[6-[2-(2,4-difluorophenyl)-1 ,1 -difluoro-

2-hydroxy-3-(1 ,2,4-triazol-1 -yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, metyltetraprole + TX, 2- (difluoromethyl)-N-((3R)-1 ,1 ,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, a-(1 ,1 -dimethylethyl)- a-[4'-(trifluoromethoxy)[1 ,T-biphenyl]-4-yl]-5-pyrimidinemethanol + TX, fluoxapiprolin + TX, enoxastrobin + TX, 4-[[6-[2-(2,4-difluorophenyl)-1 ,1 -difluoro-2-hydroxy-3-(1 ,2,4-triazol-1 -yl)propyl]-3- pyridyljoxy] benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1 ,1 -difluoro-2-hydroxy-3-(5-sulfanyl-1 ,2,4- triazol-1 -yl)propyl]-3-pyridyl]oxy] benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1 ,1 -difluoro-2-hydroxy-

3-(5-thioxo-4H-1 ,2,4-triazol-1 -yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, trinexapac + TX, coumoxystrobin + TX, zhongshengmycin + TX, thiodiazole copper + TX, zinc thiazole + TX, amectotractin + TX, iprodione + TX; N'-[5-bromo-2-methyl-6-[(1 S)-1 -methyl-2-propoxy-ethoxy]-3- pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-[(1 R)-1 -methyl-2-propoxy-ethoxy]- 3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1 -methyl-2-propoxy-ethoxy)-3- pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-chloro-2-methyl-6-(1 -methyl-2-propoxy-ethoxy)-3- pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1 -methyl-2-propoxy-ethoxy)-3- pyridyl]-N-isopropyl-N-methyl-formamidine + TX (these compounds may be prepared from the methods described in WO2015/155075); N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N- methyl-formamidine + TX (this compound may be prepared from the methods described in IPCOM000249876D); N-isopropyl-N’-[5-methoxy-2-methyl-4-(2, 2, 2-trifluoro-1 -hydroxy-1 -phenyl- ethyl)phenyl]-N-methyl-formamidine+ TX, N’-[4-(1 -cyclopropyl-2, 2, 2-trifluoro-1 -hydroxy-ethyl)-5- methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine + TX (these compounds may be prepared from the methods described in WO2018/228896); N-ethyl-N’-[5-methoxy-2-methyl-4-[2- trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine + TX, N-ethyl-N’-[5-methoxy-2-methyl-4-[2- trifuoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine + TX (these compounds may be prepared from the methods described in WO2019/1 10427); N-[(1 R)-1 -benzyl-3-chloro-1 -methyl-but-3- enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1 S)-1 -benzyl-3-chloro-1 -methyl-but-3-enyl]-8-fluoro- quinoline-3-carboxamide + TX, N-[(1 R)-1 -benzyl-3, 3, 3-trifluoro-1 -methyl-propyl]-8-fluoro-quinoline-3- carboxamide + TX, N-[(1 S)-1 -benzyl-3, 3, 3-trifluoro-1 -methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1 R)-1 -benzyl-1 ,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, N-[(1 S)-1 -benzyl- 1 , 3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, 8-fluoro-N-[(1 R)-1 -[(3- fluorophenyl)methyl]-1 ,3-dimethyl-butyl]quinoline-3-carboxamide + TX, 8-fluoro-N-[(1 S)-1 -[(3- fluorophenyl)methyl]-1 ,3-dimethyl-butyl]quinoline-3-carboxamide + TX, N-[(1 R)-1 -benzyl-1 ,3-dimethyl- butyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1 S)-1 -benzyl-1 ,3-dimethyl-butyl]-8-fluoro-quinoline-3- carboxamide + TX, N-((1 R)-1 -benzyl-3-chloro-1 -methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + TX, N-((1 S)-1 -benzyl-3-chloro-1 -methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + TX (these compounds may be prepared from the methods described in WO2017/153380); 1 -(6,7-dimethylpyrazolo[1 ,5-a]pyridin-3-yl)-4, 4, 5-trifluoro-3, 3-dimethyl-isoquinoline + TX, 1 -(6,7- dimethylpyrazolo[1 ,5-a]pyridin-3-yl)-4, 4, 6-trifluoro-3, 3-dimethyl-isoquinoline + TX, 4,4-difluoro-3,3- dimethyl-1 -(6-methylpyrazolo[1 ,5-a]pyridin-3-yl)isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1 -(7- methylpyrazolo[1 ,5-a]pyridin-3-yl)isoquinoline + TX, 1-(6-chloro-7-methyl-pyrazolo[1 ,5-a]pyridin-3-yl)-

4.4-difluoro-3, 3-dimethyl-isoquinoline + TX (these compounds may be prepared from the methods described in WO2017/025510); 1 -(4, 5-dimethylbenzimidazol-1 -yl)-4, 4, 5-trifluoro-3, 3-dimethyl- isoquinoline + TX, 1 -(4, 5-dimethylbenzimidazol-1 -yl)-4,4-difluoro-3, 3-dimethyl-isoquinoline + TX, 6- chloro-4,4-difluoro-3,3-dimethyl-1 -(4-methylbenzimidazol-1 -yl)isoquinoline + TX, 4,4-difluoro-1 -(5- fluoro-4-methyl-benzimidazol-1 -yl)-3, 3-dimethyl-isoquinoline + TX, 3-(4,4-difluoro-3,3-dimethyl-1 - isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole + TX (these compounds may be prepared from the methods described in WO2016/156085); N-methoxy-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]cyclopropanecarboxamide + TX, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1 ,2,4- oxadiazol-3-yl]phenyl]methyl]propanamide + TX, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4- oxadiazol-3-yl]phenyl]methyl]propanamide + TX, 1 -methoxy-3-methyl-1 -[[4-[5-(trifluoromethyl)-1 ,2,4- oxadiazol-3-yl]phenyl]methyl]urea + TX, 1 ,3-dimethoxy-1 -[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]urea + TX, 3-ethyl-1 -methoxy-1 -[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]urea + TX, N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX,

5.5-dimethyl-2-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, ethyl

1 -[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate + TX, N,N-dimethyl- 1 -[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]-1 ,2,4-triazol-3-amine + TX. The compounds in this paragraph may be prepared from the methods described in WO 2017/055473, WO 2017/055469, WO 2017/093348 and WO 2017/1 18689; 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3- pyridyl]-1 -(1 ,2,4-triazol-1 -yl)propan-2-ol + TX (this compound may be prepared from the methods described in WO 2017/029179); 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1 -(1 ,2,4-triazol-1 - yl)propan-2-ol + TX (this compound may be prepared from the methods described in WO 2017/029179); 3-[2-(1 -chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile + TX (this compound may be prepared from the methods described in WO 2016/156290); 3-[2-(1 - chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile + TX (this compound may be prepared from the methods described in WO 2016/156290); (4- phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate + TX (this compound may be prepared from the methods described in WO 2014/006945); 2,6-Dimethyl-1 H,5H-[1 ,4]dithiino[2,3-c:5,6- c']dipyrrole-1 ,3,5,7(2H,6H)-tetrone + TX (this compound may be prepared from the methods described in WO 201 1 /138281); N-methyl-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzenecarbothioamide + TX; N-methyl-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide + TX; (Z,2E)-5-[1 -(2,4- dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide + TX (this compound may be prepared from the methods described in WO 2018/153707); N'-(2-chloro-5-methyl-4-phenoxy- phenyl)-N-ethyl-N-methyl-formamidine + TX; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N- ethyl-N-methyl-formamidine + TX (this compound may be prepared from the methods described in WO 2016/202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl-1 ,1 -dimethyl-indan-4-yl]pyridine-3-carboxamide + TX (this compound may be prepared from the methods described in WO 2014/095675); (5-methyl-2- pyridyl)-[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methanone + TX, (3-methylisoxazol-5-yl)-[4- [5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methanone + TX (these compounds may be prepared from the methods described in WO 2017/220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1 ,2,4- oxadiazol-3-yl]phenyl]acetamide + TX (this compound may be prepared from the methods described in WO 2018/065414); ethyl 1 -[[5-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4- carboxylate + TX (this compound may be prepared from the methods described in WO 2018/158365) ; 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]acetamide + TX, N-[(E)- methoxyiminomethyl]-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide + TX, N-[(Z)- methoxyiminomethyl]-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide + TX, N-[N-methoxy-C- methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide + TX (these compounds may be prepared from the methods described in WO 2018/202428).

Most of the active ingredients described above are referred to hereinabove by a so-called "common name", the relevant "ISO common name" or another "common name" being used in individual cases. If the designation is not a "common name", the nature of the designation used instead is given in round brackets for the particular compound; in that case, the lUPAC name, the lUPAC/Chemical Abstracts name, a "chemical name", a "traditional name", a "compound name" or a "development code" is used or, if neither one of those designations nor a "common name" is used, an "alternative name" is employed.“CAS Reg. No” means the Chemical Abstracts Registry Number.

The active ingredient mixture of the compounds of formula (I) selected from a compound 1 .a.001 - 1 .a.100 to 1 .bf.001 - 1 .bf.100 described in Table 1 , and the compounds described in Table 2 (below), and an active ingredient as described above are preferably in a mixing ratio of from 100:1 to 1 :6000, especially from 50:1 to 1 :50, more especially in a ratio of from 20:1 to 1 :20, even more especially from 10:1 to 1 :10, very especially from 5:1 and 1 :5, special preference being given to a ratio of from 2:1 to 1 :2, and a ratio of from 4:1 to 2:1 being likewise preferred, above all in a ratio of 1 :1 , or 5:1 , or 5:2, or 5:3, or 5:4, or 4:1 , or 4:2, or 4:3, or 3:1 , or 3:2, or 2:1 , or 1 :5, or 2:5, or 3:5, or 4:5, or 1 :4, or 2:4, or 3:4, or 1 :3, or 2:3, or 1 :2, or 1 :600, or 1 :300, or 1 :150, or 1 :35, or 2:35, or 4:35, or 1 :75, or 2:75, or 4:75, or 1 :6000, or 1 :3000, or 1 :1500, or 1 :350, or 2:350, or 4:350, or 1 :750, or 2:750, or 4:750. Those mixing ratios are by weight.

The mixtures as described above can be used in a method for controlling pests, which comprises applying a composition comprising a mixture as described above to the pests or their environment, with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.

The mixtures comprising a compound of formula (I) selected from one of compounds 1 .a.001 - 1 .a.100 to 1 . bf.001 - 1. bf.100 described in Table 1 , and the compounds described in Table 2 (below), and one or more active ingredients as described above can be applied, for example, in a single“ready- mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a“tank-mix”, and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days. The order of applying the compounds of formula (I) selected from a compound 1 .a.001 - 1 .a.100 to 1. bf .1 - 1 . bf.100 described in Table 1 , and the compounds described in Table 2 (below), and the active ingredients) as described above, is not essential for working the present invention.

The compositions of the invention may be employed in any conventional form, for example in the form of a twin pack, a powder for dry seed treatment (DS), an emulsion for seed treatment (ES), a flowable concentrate for seed treatment (FS), a solution for seed treatment (LS), a water dispersible powder for seed treatment (WS), a capsule suspension for seed treatment (CF), a gel for seed treatment (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

Such compositions may be produced in conventional manner, e.g., by mixing the active ingredients with appropriate formulation inerts (diluents, solvents, fillers and optionally other formulating ingredients such as surfactants, biocides, anti-freeze, stickers, thickeners and compounds that provide adjuvancy effects). Also conventional slow release formulations may be employed where long lasting efficacy is intended. Particularly formulations to be applied in spraying forms, such as water dispersible concentrates (e.g. EC, SC, DC, OD, SE, EW, EO and the like), wettable powders and granules, may contain surfactants such as wetting and dispersing agents and other compounds that provide adjuvancy effects, e.g. the condensation product of formaldehyde with naphthalene sulphonate, an alkylarylsulphonate, a lignin sulphonate, a fatty alkyl sulphate, and ethoxylated alkylphenol and an ethoxylated fatty alcohol.

A seed dressing formulation is applied in a manner known per se to the seeds employing the combination of the invention and a diluent in suitable seed dressing formulation form, e.g., as an aqueous suspension or in a dry powder form having good adherence to the seeds. Such seed dressing formulations are known in the art. Seed dressing formulations may contain the single active ingredients or the combination of active ingredients in encapsulated form, e.g. as slow release capsules or microcapsules.

In general, the formulations include from 0.01 to 90% by weight of active agent, from 0 to 20% agriculturally acceptable surfactant and 10 to 99.99% solid or liquid formulation inerts and adjuvant(s), the active agent consisting of at least the compound of formula (I), and optionally other active agents, particularly microbiocides or conservatives or the like. Concentrated forms of compositions generally contain in between about 2 and 80%, preferably between about 5 and 70% by weight of active agent. Application forms of formulation may for example contain from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight of active agent. Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ diluted formulations. Table 1 below illustrates examples of individual compounds of formula (I) according to the invention.

Table 1 : Examples of individual compounds of formula (I) according to the invention.

Wherein there are: a) 100 compounds of formula (I. a):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. b) 100 compounds of formula (l.b):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. c) 100 compounds of formula (l .c)

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. d) 100 compounds of formula (l.d): wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. e) 100 compounds of formula (l.e):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. f) 100 compounds of formula (l.f):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. g) 100 compounds of formula (l.g):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. h) 100 compounds of formula (l.h): wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. i) 100 compounds of formula (l.i):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. j) 100 compounds of formula (l.j):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. k) 100 compounds of formula (I. k):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. m) 100 compounds of formula (I. m): wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. n) 100 compounds of formula (l.n):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. o) 100 compounds of formula (l.o):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. p) 100 compounds of formula (I. p):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. q) 100 compounds of formula (l.q): wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. r) 1 00 compounds of formula (l .r):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. s) 100 compounds of formula (l .s):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. t) 100 compounds of formula (l .t):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. u) 100 compounds of formula (l.u): wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. v) 100 compounds of formula (l.v):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. w) 100 compounds of formula (l.w):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. x) 100 compounds of formula (l.x):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. y) 100 compounds of formula (l.y): wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. z) 100 compounds of formula (l.z):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres.

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. ac) 100 compounds of formula (l.ac): wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. ad) 100 compounds of formula (I. ad):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. ae) 100 compounds of formula (l.ae):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. af) 100 compounds of formula (I. af):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. ag) 100 compounds of formula (l.ag): wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. ah) 100 compounds of formula (I. ah):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. ai) 100 compounds of formula (l.ai):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. aj) 100 compounds of formula (l.aj):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. ak) 100 compounds of formula (l.ak): wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. am) 100 compounds of formula (I. am):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. an) 100 compounds of formula (I. an):

wherein R¹ , R², and R³ are as defined in Table 1 . ao) 100 compounds of formula (I.ao):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. ap) 100 compounds of formula (l.ap):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. aq) 100 compounds of formula (l.aq):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. ar) 100 compounds of formula (l.ar):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. as) 100 compounds of formula (I. as):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. at) 100 compounds of formula (I. at):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. au) 100 compounds of formula (l.au): wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. av) 100 compounds of formula (l.av):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. aw) 100 compounds of formula (l.av):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. ax) 100 compounds of formula (I. ax):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. ay) 100 compounds of formula (I. ay): wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres.

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. ba) 100 compounds of formula (l.ba):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. be) 100 compounds of formula (I. be):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. bd) 100 compounds of formula (l.bd):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. bf) 100 compounds of formula (l.bf):

wherein R¹ , R², and R³ are as defined in Table 1 , and wherein the symbols * and ** indicate the locations of chiral centres. Formulation Examples

Wettable powders a) b) c)

active ingredient [compound of formula (I)] 25 % 50 % 75 %

sodium lignosulfonate 5 % 5 %

sodium lauryl sulfate 3 % 5 %

sodium diisobutylnaphthalenesulfonate 6 % 10 %

phenol polyethylene glycol ether 2 %

(7-8 mol of ethylene oxide)

highly dispersed silicic acid 5 % 10 % 10 %

Kaolin 62 % 27 %

The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with waterto give suspensions of the desired concentration.

Powders for dry seed treatment a) b) c)

active ingredient [compound of formula (I)] 25 % 50 % 75 %

light mineral oil 5 % 5 % 5 %

highly dispersed silicic acid 5 % 5 %

Kaolin 65 % 40 %

Talcum 20 %

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

Emulsifiable concentrate

active ingredient [compound of formula (I)] 10 %

octylphenol polyethylene glycol ether 3 %

(4-5 mol of ethylene oxide)

calcium dodecylbenzenesulfonate 3 %

castor oil polyglycol ether (35 mol of ethylene oxide) 4 %

Cyclohexanone 30 %

xylene mixture 50 %

Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water. Dusts a) b) c)

Active ingredient [compound of formula (I)] 5 % 6 % 4 % talcum 95 %

Kaolin 94 %

mineral filler 96 %

Ready-for-use dusts are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.

Extruder granules

Active ingredient [compound of formula (I)] 15 %

sodium lignosulfonate 2 %

carboxymethylcellulose 1 %

Kaolin 82 %

The active ingredient is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

Coated granules

Active ingredient [compound of formula (I)] 8 %

polyethylene glycol (mol. wt. 200) 3 %

Kaolin 89 % The finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.

Suspension concentrate

active ingredient [compound of formula (I)] 40 %

propylene glycol 10 %

nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 %

Sodium lignosulfonate 10 %

carboxymethylcellulose 1 %

silicone oil (in the form of a 75 % emulsion in water) 1 %

Water 32 % The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion. Flowable concentrate for seed treatment active ingredient [compound of formula (I)] 40 %

propylene glycol 5 %

copolymer butanol PO/EO 2 %

tristyrenephenole with 10-20 moles EO 2 %

1 ,2-benzisothiazolin-3-one (in the form of a 20% solution in water) 0.5 %

monoazo-pigment calcium salt 5 %

Silicone oil (in the form of a 75 % emulsion in water) 0.2 %

Water 45.3 %

The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

Slow Release Capsule Suspension

28 parts of a combination of the compound of formula (I) are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1 ). This mixture is emulsified in a mixture of 1 .2 parts of polyvinyl alcohol, 0.05 parts of a defoamer and 51 .6 parts of water until the desired particle size is achieved. To this emulsion a mixture of 2.8 parts 1 ,6-diaminohexane in 5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed.

The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingredients. The medium capsule diameter is 8-15 microns.

The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.

Examples

The Examples which follow serve to illustrate the invention. The compounds of the invention can be distinguished from known compounds by virtue of greater efficacy at low application rates, which can be verified by the person skilled in the art using the experimental procedures outlined in the Examples, using lower application rates if necessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1 .5 ppm, 0.8 ppm or 0.2 ppm.

Compounds of formula (I) may possess any number of benefits including, inter alia, advantageous levels of biological activity for protecting plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingredients (for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile (including improved crop tolerance), improved physico-chemical properties, or increased biodegradability). List of Abbreviations

°C degrees Celsius

CDCb chloroform-d

DCM dichloromethane

DIPEA N,N-Diisopropylethylamine

DMAP 4-Dimethylaminopyridine

EDCI 1 -ethyl-3-(3-dimethylaminopropyl)carbodiimide

d doublet

dr diastereomeric ratio

m multiplet

MHz mega hertz

mp melting point

ppm parts per million

PyBop benzotriazol-1 -yl-oxytripyrrolidinophosphonium hexafluorophosphate

q quartet

s singlet

THF tetrahydrofuran

Examples

Example 1 : This example illustrates the preparation of [2-[[(1 S)-2-[2-(3,5-dichloro-2-pyridyl)-1 -methyl- propoxy]-1 -methyl-2-oxo-ethyl]carbamoyl]-4-methoxy-3-pyridyl]oxymethyl 2-methylpropanoate a) Preparation of 1 -(3,5-dichloro-2-pyridyl)propan-2-one

Acetic anhydride

N-Methylimidazole

In a round bottom flask 2-(3,5-dichloropyridin-2-yl)acetic acid (100 g, 485.4 mmol, 1 equiv.) was mixed with acetic anhydride (5 equiv.) under an argon atmosphere at room temperature. 1 -methylimidazole (0.5 equiv.) was slowly added to the stirred mixture and the reaction was stirred at room temperature for 3 days. Then the temperature was lowered to 0°C and water (500 mL) was carefully added to the mixture and the reaction was stirred for 1 additional hour at room temperature. Next the water phase was extracted three times with ethyl acetate and the combined organic phases washed with NaOHaq (1 M), water and brine. The resulting organic phase was dried over sodium sulphate and concentrated under vacuo. Purification by chromatography on silica gel (eluent: mixtures heptane/ethyl acetate) gave the desired 1 -(3,5-dichloro-2-pyridyl)propan-2-one (37.2 g, 38% yield). ¹H-NMR (400 MHz, CDCb): d = 2.28

(s, 3H), 4.12 (s, 2H), 7.74 (d, 1 H), 8.43 (d, 1 H). b) Preparation of 3-(3,5-dichloro-2-pyridyl)butan-2-one In a round bottom flask under an argon atmosphere, sodium hydride (60% in mineral oil, 1 .05 equiv.) was suspended in THF (180 mL) and the temperature was lowered to 0°C. Next a solution of 1 -(3,5- dichloro-2-pyridyl)propan-2-one in THF (36.0 g, 1 equiv., in 173 mL) was added dropwise and the resulting mixture was stirred at 0°C for 30 min. Then iodomethane (1 .05 equiv.) was added dropwise at 0°C and the temperature allowed to reach room temperature. After two hours the reaction was carefully quenched with water and the mixture was extracted with ethyl acetate three times. The combined organic phases were washed with water and brine, dried over sodium sulphate and concentrated in vacuo. The desired 3-(3,5-dichloro-2-pyridyl)butan-2-one (38.5 g, 84.5% yield) was obtained after purification by chromatography on silica gel (eluent: heptane/ethyl acetate). ¹H-NMR (400 MHz, CDCb): d = 1 .58 (d, 3H), 2.15 (s, 3H), 4.37 (q, 1 H), 7.74 (d, 1 H), 8.45 (d, 1 H). c) Preparation of 3-(3,5-dichloro-2-pyridyl)butan-2-ol

rac

In a round bottom flask 3-(3,5-dichloro-2-pyridyl)butan-2-one (32.5 g, 1 .0 equiv.) was dissolved in THF (745 mL) under argon and the solution stirred at room temperature. Zinc chloride (1 .4 equiv.) was added portionwise and the mixture stirred for 30 additional minutes. The temperature was cooled to 0°C and sodium borohydride (1 .1 equiv.) was added portionwise. The reaction was stirred for 1 hour at 0°C, then a saturated ammonium chloride aqueous solution and ethyl acetate were added in sequence. THF was distilled off using a rotatory evaporator, the phases separated and the aqueous layer extracted with additional ethyl acetate. The combined organic phases were dried over sodium sulphate and the volatiles evaporated in vacuo. The desired 3-(3,5-dichloro-2-pyridyl)butan-2-ol (30.9 g, 94% yield, dr = 6:1) was obtained after purification by chromatography on silica gel (eluent: mixtures heptane/ethyl acetate). The two diastereoisomers are described as A (major) and B (minor): ¹H-NMR (400 MHz, CDCb): 5 = 1 .18-1 .35 (m, 6H A + 6H B), 3.20-3.33 (m, 1 H A), 3.35-3.45 (m, 1 H B), 4.06-4.18 (m, 1 H B), 4.20-4.30 (m, 1 H A), 4.50 (bs, 1 H A +1 H B), 7.70-7.80 (m, 1 H A +1 H B), 8.35-8.45 (m, 1 H A +1 H B). d) Preparation of [2-(3,5-dichloro-2-pyridyl)-1 -methyl-propyl] (2S)-2-(tert-butoxycarbonylamino) propanoate 3-(3,5-dichloro-2-pyridyl)butan-2-ol (dr = 6:1 , 41 g, 1 .0 equiv.) was dissolved in DCM (1 .5 L) under argon at room temperature. The solution was stirred at 0°C and then Boc-alanine (38.8 g, 1 .1 equiv.) and DMAP (0.1 equiv.) were added in sequence. Next, 1 -(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride was added slowly and the resulting mixture was allowed to reach room temperature and stirred for 15 hours. Next, all the volatiles were removed by rotatory evaporation and the crude material purified by chromatography on silica gel (eluent: mixtures heptane/ethyl acetate). The desired [2-(3,5- dichloro-2-pyridyl)-1 -methyl-propyl] (2S)-2-(tert-butoxycarbonylamino)propanoate was obtained as mixture of diastereoisomers (47.5 g, 65% yield). ¹H-NMR (400 MHz, CDC ): d = 0.90-1 .65 (m, 18 H), 3.55-3.70 (m, 1 H), 4.30-4.45 (m, 1 H), 5.0-5.25 (m, 1 H), 5.40-5.50 (m, 1 H), 7.60-7.75 (m, 1 H), 8.40-8.50 (m, 1 H). e) Preparation of [(1 S)-2-[2-(3,5-dichloro-2-pyridyl)-1 -methyl-propoxy]-1 -methyl-2-oxo-ethyl]ammonium chloride

In a round bottom flask, a 4M HCI solution in dioxane (10 equiv.) was added to a stirred solution of [2- (3, 5-dichloro-2-pyridyl)-1 -methyl-propyl] (2S)-2-(tert-butoxycarbonylamino)propanoate (mixture of diastereoisomers, 47.0 g, 1 .0 equiv.) in DCM (600 ml_). The reaction was stirred at room temperature for 1 h and concentrated in vacuo to yield the desired product, which was used in the next step without further purification. f) Preparation of [2-(3,5-dichloro-2-pyridyl)-1 -methyl-propyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2- carbonyl)amino]propanoate

Under argon [(1 S)-2-[2-(3,5-dichloro-2-pyridyl)-1 -methyl-propoxy]-1 -methyl-2-oxo-ethyl]ammonium chloride (mixture of diastereoisomers, 37.2 g, 1 .0 equiv.) was dissolved in DCM (570 ml_) in a round bottom flask and 3-hydroxy-4-methoxypyridine-2-carboxylic acid (1 .1 equiv.) was added. PyBop (1 .1 equiv.) and DIPEA (3.3 equiv.) were added in sequence to the stirred mixture and the reaction was stirred at room temperature for 2 hours. Next the mixture was concentrated in vacuo and the desired product was obtained by chromatography on silica gel (eluent: mixtures heptane/ethyl acetate). [2-(3,5- dichloro-2-pyridyl)-1 -methyl-propyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino] propanoate is obtained as a mixture of diastereoisomers (dr = 6:6:1 :1 , 41 g, 82% yield). The four diastereoisomers are described as A (first major), B (second major), C (first minor), D (second minor). Ή-NMR (400 MHz, CDC ): d = 1 .10-1 .65 (m, 9H A + 9H B + 9H C + 9H D), 3.55-3.75 (m, 1 H A + 1 H B + 1 H C + 1 H D), 3.97 (s, 3H A + 3H B + 3H C + 3H D), 4.40-4.60 (1 H C + 1 H D), 4.65-4.80 (1 H A + 1 H B), 5.30-5.50 (m, 1 H A + 1 H B + 1 H C + 1 H D), 6.80-6.90 (m, 1 H A + 1 H B + 1 H C + 1 H D), 7.55- 7.65 (m, 1 H C + 1 H D), 7.65-7.75 (m, 1 H A + 1 H B), 7.95-8.05 (m, 1 H A + 1 H B + 1 H C + 1 H D), 8.25- 8.38 (m, 1 H C + 1 H D), 8.38-8.43 (m, 1 H C + 1 H D), 8.43-8.46 (m, 1 H A + 1 H B), 8.47-8.60 (m, 1 H A + 1 H B), 12.05-12.15 (m, 1 H C + 1 H D), 12.15-12.25 (m, 1 H A + 1 H B).

Separation of diastereoisomers was obtained by preparative HPLC. The details of the method can be found below:

Sepiatec Prep SFC 100

Column: Daicel CHIRALPAK® IF, 5pm, 2.0 cm x 25cm

Mobile phase: A: CO2 B: EtOH+0.1 %TFA isocratic: 10% B in 10 min

Backpressure: 150 bar

Flow rate: 60 ml/min

GLS pump: 4ml/min EtOAc

Detection: UV 280 nm

Sample concentration: 93 mg/ml_ in MeOH

Injection: 200-500mI

g) Preparation of [2-[[(1 S)-2-[2-(3,5-dichloro-2-pyridyl)-1 -methyl-propoxy]-1 -methyl-2-oxo- ethyl]carbamoyl]-4-methoxy-3-pyridyl]oxymethyl 2-methylpropanoate mixture of diastereoisomers (dr = 6:6:1 :1). Under argon [2-(3,5-dichloro-2-pyridyl)-1 -methyl-propyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2- carbonyl)amino]propanoate (as a mixture of diastereoisomers A B C D = 6:6:1 A , 687 mg, 1 .0 equiv.) was dissolved in acetone (8 ml_) and stirred at room temperature in a round bottom flask. Sodium iodide (1 .0 equiv.), sodium carbonate (3.0 equiv.) and chloromethyl isobutyrate (2.0 equiv.) were added in sequence and the mixture was stirred 6 hours at room temperature. Ethyl acetate was added and acetone distilled off using a rotatory evaporator. The organic phase was washed with water and brine, then dried over sodium sulphate and concentrated in vacuo. The desired product was obtained after purification by chromatography on silica gel (eluent: mixtures heptane/ethyl acetate). [2-[[(1 S)-2-[2-(3,5- dichloro-2-pyridyl)-1 -methyl-propoxy]-1 -methyl-2-oxo-ethyl]carbamoyl]-4-methoxy-3-pyridyl]oxymethyl 2-methylpropanoate was obtained as mixture of diastereoisomers (674 mg, 82% yield, dr = 6:6:1 :1 ), which are here described as A (first major), B (second major), C (first minor), D (second minor). ¹H-NMR (400 MHz, CDC ): d = 1 .00-1 .65 (m, 15H A + 15H B + 15H C + 15H D), 2.45-2.55 (m, 1 H A + 1 H B + 1 H C + 1 H D), 3.60-3.70 (m, 1 H A + 1 H B + 1 H C + 1 H D), 3.90 (s, 3H A + 3H B + 3H C + 3H D), 4.45- 4.60 (1 H C + 1 H D), 4.70-4.85 (1 H A + 1 H B), 5.30-5.50 (m, 1 H A + 1 H B + 1 H C + 1 H D), 5.75-5.85 (m, 2H A + 2H B + 2H C + 2H D), 6.90-6.95 (m, 1 H A + 1 H B + 1 H C + 1 H D), 7.60-7.65 (m, 1 H C + 1 H D), 7.65-7.75 (m, 1 H A + 1 H B), 8.25-8.35 (m, 1 H A + 1 H B + 1 H C + 1 H D), 8.40-8.55 (m, 2H A + 2H B + 2H C + 2H D). g) Preparation of [2-[[(1 S)-2-[2-(3,5-dichloro-2-pyridyl)-1 -methyl-propoxy]-1 -methyl-2-oxo- ethyl]carbamoyl]-4-methoxy-3-pyridyl]oxymethyl 2-methylpropanoate as single diastereoisomer (isomer A).

Under argon [2-(3,5-dichloro-2-pyridyl)-1 -methyl-propyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2- carbonyl)amino]propanoate (single isomer A from example (F), 18.0 g, 1 .0 equiv.) was dissolved in acetone (210 ml_) and stirred at room temperature in a round bottom flask. Sodium iodide (1 .0 equiv.), sodium carbonate (3.0 equiv.) and chloromethyl isobutyrate (2.0 equiv.) were added in sequence and the mixture stirred for 6 hours at room temperature. Ethyl acetate was added and acetone distilled off using a rotatory evaporator. The organic phase was washed with water and brine, then dried over sodium sulphate and concentrated in vacuo. The desired product was obtained after purification by chromatography on silica gel (eluent: mixtures heptane/ethyl acetate). [2-[[(1 S)-2-[2-(3,5-dichloro-2- pyridyl)-1 -methyl-propoxy]-1 -methyl-2-oxo-ethyl]carbamoyl]-4-methoxy-3-pyridyl]oxymethyl 2-methyl propanoate was obtained as single diastereoisomer (14.4 g, 65.2% yield, isomer A). ¹H-NMR (400 MHz, CDCb): d = 1 .00-1 .65 (m, 15H), 2.45-2.55 (m, 1 H), 3.60-3.70 (m, 1 H), 3.90 (s, 3H), 4.70-4.85 (1 H), 5.35- 5.45 (m, 1 H), 5.75-5.82 (m, 2H), 6.95 (d, 1 H), 7.68 (d, 1 H), 8.28 (d, 1 H), 8.40-8.50 (m, 2H). Table 2 below illustrates exemplified individual compounds of formula (I) according to the invention.

Throughout this description, temperatures are given in degrees Celsius (°C) and“m.p.” means melting point. LC/MS means Liquid Chromatography Mass Spectrometry and the description of the apparatus and the method is: (Method A ACQUITY UPLC from Waters, Waters UPLC HSS T3, 1 .8 mhi particle size, 30 x 2.1 mm column, 0.85 mL/min., 60 °C, H₂0/MeOH 95:5 + 0.05% HCOOH (90%) / CHsCN + 0.05% HCOOH (10%) - 1 .2 min. - CH₃CN + 0.05% HCOOH (100%) - 0.30 min., ACQUITY SQD Mass Spectrometer from Waters, ionization method: electrospray (ESI), Polarity: positive ions, Capillary (kV) 3.00, Cone (V) 30.00, Extractor (V) 2.00, Source Temperature (°C) 150, Desolvation Temperature (°C) 350, Cone Gas Flow (L/Hr) 0, Desolvation Gas Flow (L/Hr) 650). Method B: ACQUITY UPLC from Waters, Waters UPLC HSS T3, 1 .8 mhi particle size, 30 x 2.1 mm column, 0.85 mL/min., 60 °C, H₂0/Me0H 95:5 + 0.05% HCOOH (90%) / CH₃CN + 0.05% HCOOH (10%) - 2.7 min. - CH₃CN + 0.05% HCOOH (100%) - 0.30 min., ACQUITY SQD Mass Spectrometer from Waters, ionization method: electrospray (ESI), Polarity: positive ions, Capillary (kV) 3.00, Cone (V) 30.00, Extractor (V) 2.00, Source Temperature (°C) 150, Desolvation Temperature (°C) 350, Cone Gas Flow (L/Hr) 0, Desolvation Gas Flow (L/Hr) 650)).

Table 2: LC/MS data (R_t = Retention time) for selected compounds of Table 1.

Biological examples

Botryotinia fuckeliana (Botrytis cinerea) / liquid culture (Gray mould)

Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (Vogels broth). After placing a (DMSO) solution of test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24 °C and the inhibition of growth is determined photometrically 3-4 days after application. The following compounds gave at least 80% control of Botryotinia fuckeliana at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: E-2, E-3.

Glomerella lagenarium (Colletotrichum lagenarium) / liquid culture (Anthracnose)

Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24 °C and the inhibition of growth is measured photometrically 3-4 days after application. The following compounds gave at least 80% control of Glomerella lagenarium at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: E-1 , E-2.

Blumeria graminis f. sp. tritici (Erysiphe graminis f. sp. tritici) / wheat / leaf disc preventative (Powdery mildew on wheat)

Wheat leaf segments cv. Kanzler are placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks are inoculated by shaking powdery mildew infected plants above the test plates 1 day after application. The inoculated leaf disks are incubated at 20 °C and 60% rh under a light regime of 24 h darkness followed by 12 h light / 12 h darkness in a climate chamber and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears on untreated check leaf segments (6 - 8 days after application). The following compounds gave at least 80% control of Blumeria graminis f. sp. tritici at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: E-1 .

Phaeosphaeria nodorum (Septoria nodorum) / wheat / leaf disc preventative (Glume blotch)

Wheat leaf segments cv. Kanzler are placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks are inoculated with a spore suspension of the fungus 2 days after application. The inoculated test leaf disks are incubated at 20 °C and 75% rh under a light regime of 12 h light / 12 h darkness in a climate cabinet and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf disks (5 - 7 days after application). The following compounds gave at least 80% control of Phaeosphaeria nodorum at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: E-1 , E-2, E-6, E-7. Monographella nivalis (Microdochium nivale) / liquid culture (foot rot cereals)

Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24 °C and the inhibition of growth is determined photometrically 4-5 days after application. The following compounds gave at least 80% control of Monographella nivalis at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: E-1 , E-2, E-3, E-4, E-5, E-6, E-7.

Mycosphaerella arachidis (Cercospora arachidicola) / liquid culture (early leaf spot)

Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24 °C and the inhibition of growth is determined photometrically 4-5 days after application. The following compounds gave at least 80% control of Mycosphaerella arachidis at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: E-1 , E-2, E-3, E-4, E-6, E- 7.

Phakopsora pachyrhizi /soybean /preventative (soybean rust)

Soybean leaf disks are placed on water agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. One day after application leaf discs are inoculated by spraying a spore suspension on the lower leaf surface. After an incubation period in a climate cabinet of 24-36 hours in darkness at 20 °C and 75% rh leaf disc are kept at 20 °C with 12 h light/day and 75% rh. The activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf disks (12 - 14 days after application). The following compounds gave at least 80% control of Phakopsora pachyrhizi at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: E-1 , E-2, E-3, E-6, E-7.

Puccinia recondita f. sp. tritici / wheat / leaf disc curative (Brown rust)

Wheat leaf segments cv. Kanzler are placed on agar in multiwell plates (24-well format). The leaf segments are inoculated with a spore suspension of the fungus. Plates are stored in darkness at 19 °C and 75% rh. The formulated test compound diluted in water is applied 1 day after inoculation. The leaf segments are incubated at 19 °C and 75% rh under a light regime of 12 h light / 12 h darkness in a climate cabinet and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (6 - 8 days after application). The following compounds gave at least 80% control of Puccinia recondita f. sp. tritici at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: E-1 , E-2, E-3, E-4, E-6, E-7. Puccinia recondite f. sp. tritici / wheat / leaf disc preventative (Brown rust)

Wheat leaf segments cv. Kanzler are placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks are inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf segments are incubated at 19 °C and 75% rh under a light regime of 12 h light / 12 h darkness in a climate cabinet and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (7 - 9 days after application). The following compounds gave at least 80% control of Puccinia recondita f. sp. tritici at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: E-1 , E-2, E-6, E-7.

Magnaporthe grisea (Pyricularia oryzae) / rice / leaf disc preventative (Rice Blast)

Rice leaf segments cv. Ballila are placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water. The leaf segments are inoculated with a spore suspension of the fungus 2 days after application. The inoculated leaf segments are incubated at 22 °C and 80% rh under a light regime of 24 h darkness followed by 12 h light / 12 h darkness in a climate cabinet and the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (5 - 7 days after application). The following compounds gave at least 80% control of Magnaporthe grisea at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: E-1 , E-2, E-4, E-6, E-7.

Sclerotinia sclerotiorum / liquid culture (cottony rot)

Mycelia fragments of a newly grown liquid culture of the fungus are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of test compound into a microtiter plate (96-well format) the nutrient broth containing the fungal material is added. The test plates are incubated at 24 °C and the inhibition of growth is determined photometrically 3-4 days after application. The following compounds gave at least 80% control of Sclerotinia sclerotiorum at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: E-1 , E- 2, E-3, E-6.

Mycosphaerella graminicola (Septoria tritici) / liquid culture (Septoria blotch)

Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24 °C and the inhibition of growth is determined photometrically 4-5 days after application. The following compounds gave at least 80% control of Mycosphaerella graminicola at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: E-1 , E-2, E-3, E-4, E-5, E- 6, E-7.

Claims

Claims:

1 . A diastereomer, or mixture of diastereomers, of a compound of formula (I):

wherein,

R² is Ci-Ci2alkyl, Cs-Cscycloalkyl, Ci-C6haloalkyl, Ci-C6alkoxyCi-C6alkyl, or C3- C8halocycloalkyl;

R³ is Ci-Ci2alkyl or Cs-Cscycloalkyl;

2. The diastereomer, or mixture of diastereomers, according to claim 1 , wherein the compound of formula (I) is in the (R,R,S)-, (S,S,S)-, (S,R,S)- and/or (R,S,S)- diastereomeric form(s).

3. The diastereomer, or mixture of diastereomers, according to claim 1 or claim 2, wherein R¹ is hydroxy, acetoxy, propanoyloxy, acetoxymethoxy, propanoyloxymethoxy, or 2-methyl- propanoyloxymethoxy.

4. The diastereomer, or mixture of diastereomers, according to any one of claims 1 to 3, wherein R² and R³ are each independently Ci-C₄alkyl.

5. The diastereomer, or mixture of diastereomers, according to any one of claims 1 to 4, wherein R⁴ is heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered aromatic ring which comprises 1 , 2 or 3 heteroatoms individually selected from N, O and S, and wherein the heteroaryl moiety is optionally substituted by 1 , 2 or 3 substituents, which may be the same or different, selected from R⁵.

6. The diastereomer, or mixture of diastereomers, according to any one of claims 1 to 5, wherein R⁴ is heteroaryl, wherein the heteroaryl moiety is a 6-membered aromatic ring which comprises 1 or 2 heteroatoms individually selected from N, O and S, and wherein the heteroaryl moiety is optionally substituted by 1 or 2 substituents, which may be the same or different, selected from R⁵.

7. The diastereomer, or mixture of diastereomers, according to any one of claims 1 to 6, wherein R⁵ is fluoro, chloro, methyl, or trifluoromethyl.

8. The diastereomer, or mixture of diastereomers, according to any one of claims 1 to 7, wherein the compound of formula (I) is a mixture of compounds of formula (l-a), (l-b), (l-c), (l-d), (l-e), (l-f), (l-g), and (l-h).

9. The diastereomer, or mixture of diastereomers, according to any one of claims 1 to 8, wherein the compound of formula (I) is a mixture of compounds of formula (l-a), (l-b), (l-c), and (l-d).

10. The diastereomer, or mixture of diastereomers, according to any one of claims 1 to 9, wherein the compound of formula (I) is a mixture of compounds of formula (l-a), (l-b), (l-c), and (l-d) in a molar ratio of 99:0.3:0.3:0.3 to 0.3:99:0.3:0.3 to 0.3:0.3:99:0.3 to 0.3:0.3:0.3:99.

1 1 . The diastereomer, or mixture of diastereomers, according to any one of claims 1 to 10, wherein the compound of formula (I) is a mixture of compounds of formula (l-a), (l-b), (l-c), and (l-d) in a molar ratio of 10:1 :1 :1 to 1 :10:1 :1 to 1 :1 :10:1 to 1 :1 :1 :10.

12. An agrochemical composition comprising a fungicidally effective amount of a diastereomer, or mixture of diastereomers, of a compound of formula (I) according to any one of claims 1 to 1 1 .

13. The composition according to claim 12, further comprising at least one additional active ingredient and/or an agrochemically-acceptable diluent or carrier.

14. A method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a fungicidally effective amount of a diastereomer, or mixture of diastereomers, of a compound of formula (I) according to any of claims 1 to 1 1 , or a composition comprising this compound as active ingredient, is applied to the plants, to parts thereof or the locus thereof.

15. Use of a diastereomer, or mixture of diastereomers, of a compound of formula (I) according to any one of claims 1 to 1 1 as a fungicide.