Microbiocidal Compounds

The present invention relates to microbiocidal tetrazolone derivatives, e.g. , as active ingredients, which have microbiocidal activity, in particular, fungicidal activity. The invention also relates to agrochemical compositions which comprise at least one of the tetrazolone derivatives, to processes of preparation of these compounds and to uses of the tetrazolone derivatives or compositions in agriculture or horticulture for controlling or preventing infestation of plants, harvested food crops, seeds or nonliving materials by phytopathogenic microorganisms, preferably fungi. JP09208565 and WO2016/088747 describe the use of tetrazolone derivatives for combating phytopathogenic fungi.

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

wherein

R is hydrogen, methyl or halogen; R ² is hydrogen, halogen, cyano, Ci-4alkyl, C2-4alkenyl, C2-4alkynyl, Ci-4haloalkyl, Ci-4alkoxy, Ci-

4haloalkoxy, Ci-4alkylsulfanyl, Ci-4haloalkylsulfanyl, C3-6cycloalkyl or Cs ehalocycloalkyl;

R ³ is hydrogen, Ci-4alkyl, Ci-4haloalkyl, C3-6cycloalkyl or C3-6cycloalkylCi-2alkyl-; R ⁴ is Ci-4alkyl, C2-4alkenyl, C2-4alkynyl, Ci-4haloalkyl, C2-4haloalkenyl, C2-4haloalkynyl or C3-

6cycloalkyl;

R ⁵ is hydrogen, Ci-ealkyl, C2-6alkenyl, C2-6alkynyl, Ci ehaloalkyl, C2-6haloalkenyl, C2-6haloalkynyl, Ci-4alkoxyCi-2alkyl-, Ci-4haloalkoxyCi-2alkyl-, C3-6cycloalkyl, Cs ehalocycloalkyl, C3-6cycloalkylCi-2alkyl-, C3-6cycloalkylC2-3alkenyl- or C3-6halocycloalkylCi-2alkyl-;

R ⁶ is hydrogen, Ci-4alkyl, C2-4alkenyl, C2-4alkynyl, Ci-4haloalkyl, C2-4haloalkenyl, C2-4haloalkynyl, Ci-2alkoxyCi-2alkyl-, Cs ecycloalkyl or C3-6cycloalkylCi-2alkyl-; including a geometrical isomer thereof; or an agronomically acceptable salt thereof. It has been found that the novel compounds of formula (I) have, 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 compound of formula (I) and an agrochemically- acceptable diluent or carrier. Such an agricultural composition may further comprise at least one additional active ingredient.

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 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 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.

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

As used herein, cyano means a -CN group.

As used herein, hydroxy means an -OH group.

As used herein, the term "Ci-6alkyl" 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. Ci-4alkyl and Ci-2alkyl are to be construed accordingly. Examples of d ealkyl include, but are not limited to, methyl, ethyl, n- propyl, 1-methylethyl (/so-propyl), n-butyl, and 1-dimethylethyl (i-butyl).

As used herein, the term "Ci-4alkoxy" refers to a radical of the formula -OR _a where R _a is a Ci- C4alkyl radical as generally defined above. Ci-2alkoxy is to be construed accordingly. Examples of Ci- 4alkoxy include, but are not limited to, methoxy, ethoxy, propoxy, / ^' so-propoxy, i-butoxy.

As used herein, the term "Ci-6haloalkyl" refers to a d ealkyl radical as generally defined above substituted by one or more of the same or different halogen atoms. Ci-4haloalkyl and Ci-2haloalkyl are to be construed accordingly. Examples of C-i ehaloalkyl include, but are not limited to chloromethyl, fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl.

As used herein, the term "C2-6alkenyl" 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 (Z)-configuration, having from two to six carbon atoms, which is attached to the rest of the molecule by a single bond . C2-4alkenyl is be construed accordingly. Examples of C2-C6alkenyl include, but are not limited to, prop-1-enyl, allyl (prop-2-enyl), but-1-enyl.

As used herein, the term "C2-6haloalkenyl" refers to a C2-C6alkenyl radical as generally defined above substituted by one or more of the same or different halogen atoms. C2-4haloalkenyl is be construed accordingly. Examples of C2-6haloalkenyl include, but are not limited to chloroethylene, fluoroethylene, 1 ,1-difluoroethylene, 1 ,1-dichloroethylene, 1 ,1 ,2-trichloroethylene.

As used herein, the term "C2-6alkynyl" 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 . C2-4alkynyl is to be construed accordingly. Examples of C2-6alkynyl include, but are not limited to, prop-1-ynyl, propargyl (prop-2-ynyl), but-1-ynyl.

As used herein, the term "C2-6haloalkynyl" refers to a C2-C6alkynyl radical as generally defined above substituted by one or more of the same or different halogen atoms. C2-4haloalkynyl is to be construed accordingly.

As used herein, the term "Ci-4haloalkoxy" refers to a Ci-4alkoxy group as defined above substituted by one or more of the same or different halogen atoms. Ci-2haloalkoxy is to be construed accordingly. Examples of Ci-4haloalkoxy include, but are not limited to, fluoromethoxy, difluoromethoxy, fluoroethoxy, trifluoromethoxy, trifluoroethoxy.

As used herein, the term "Ci-4alkylsulfanyl" refers to a radical of the formula -SR _a where R _a is a Ci C4alkyl radical as generally defined above.

As used herein, the term "Ci-4haloalkylsulfanyl" refers to a Ci-4alkylsulfanyl group as defined above substituted by one or more of the same or different halogen atoms.

As used herein, the term "Ci-4alkoxyCi-2alkyl-" refers to radical of the formula R _a -0-Rb- where Rb is a Ci-4alkyl radical as generally defined above, and Rb is a Ci-2alkylene radical as generally defined above. Ci-2alkoxyCi-2alkyl is to be construed accordingly.

As used herein, the term "Ci-4haloalkoxyCi-2alkyl-" refers to radical of the formula R _a -0-Rb- where R _a is a Ci-4haloalkyl radical as generally defined above, and Rb is a Ci-2alkylene radical as generally defined above. Ci-2haloalkoxyCi-2alkyl is to be construed accordingly.

As used herein, the term "C3-6cycloalkyl" refers to a stable, monocyclic ring radical which is saturated or partially unsaturated and contains 3 to 6 carbon atoms. C3-4cycloalkyl is to be construed accordingly. Examples of C3-6cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

As used herein, the term "C3-6halocycloalkyl" refers to a C3-6cycloalkyl radical as generally defined above substituted by one or more of the same or different halogen atoms. C3-4halocycloalkyl is to be construed accordingly.

As used herein, the term "C3-6cycloalkylCi-2alkyl-" refers to a C3-6cycloalkyl ring as defined above attached to the rest of the molecule by a Ci-2alkylene radical as defined above. The term "C3- 4cycloalkylCi-2alkyl" is to be construed accordingly. Examples of C3-6cycloalkylCi-2alkyl include, but are not limited to cyclopropyl-m ethyl- and cyclobutyl-ethyk

As used herein, the term "C3-6cycloalkylC2-3alkenyl-" refers to a C3-6cycloalkyl ring as defined above attached to the rest of the molecule by a C2-3alkenyl radical as defined above, containing at least one double bond that can be of either the (E)- or (Z)-configu ration, having from two to three carbon atoms, which is attached to the rest of the molecule by a single bond.

As used herein, the term "C3-6halocycloalkylCi-2alkyl" refers to a Cs ehalocycloalkyl ring as defined above attached to the rest of the molecule by a Ci-2alkylene radical as defined above. The term "C3-4halocycloalkylCi-2alkyl" is to be construed accordingly.

The compound of formula (I) may exist as E and/or Z isomers. This invention covers all such isomers and mixtures thereof in all proportions.

For example a compound of formula (I) can be drawn in at least 8 different isomeric forms shown below.

The presence of one or more possible asymmetric carbon atoms in a compound of formula (I) means that the compounds may occur in chiral 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 (including lactam-lactim tautomerism and keto- enol tautomerism) where present. 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 covalently hydrated form, or in salt form, e.g., an agronomically usable or agrochemically acceptable salt form.

The following list provides definitions, including preferred definitions, for substituents R , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ with reference to the compounds of formula (I) according to the invention. 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.

R is hydrogen, methyl or halogen. Preferably, R is hydrogen or methyl. Most preferably, R is hydrogen.

R ² is hydrogen, halogen, cyano, Ci-4alkyl, C2-4alkenyl, C2-4alkynyl, Ci-4haloalkyl, Ci-4alkoxy, Ci- 4haloalkoxy, Ci-4alkylsulfanyl, Ci-4haloalkylsulfanyl, C3-6cycloalkyl or Cs ehalocycloalkyl. Preferably, R ² is hydrogen, halogen, Ci-4alkyl, Ci-4haloalkyl, Ci-4alkoxy, Ci-4haloalkoxy, C3-6cycloalkyl, or C3- 6halocycloalkyl. More preferably, R ² is hydrogen, halogen, Ci-4alkyl or Ci-4alkoxy. Even more preferably, R ² is halogen or Ci-4alkyl. Even more preferably still, R ² is bromo, methyl or ethyl. Most preferably, R ² is methyl.

In one embodiment R ² is halogen, Ci-4alkyl or C3-6cycloalkyl. Preferably R ² is bromo, chloro, methyl, ethyl or cyclopropyl.

R ³ is hydrogen, Ci-4alkyl, Ci-4haloalkyl, C3-6cycloalkyl or C3-6cycloalkylCi-2alkyk Preferably, R ³ is hydrogen, Ci-4alkyl, C3-4cycloalkyl or C3-4cycloalkylCi-2alkyl. More preferably, R ³ is hydrogen or Ci- 4alkyl. Even more preferably, R ³ is Ci-4alkyl. Most preferably, R ³ is methyl or ethyl.

In one embodiment R ³ is Ci-4alkyl, Ci-4haloalkyl, C3-6cycloalkyl or C3-6cycloalkylCi-2alkyl. Preferably R ³ is Ci-4alkyl, Ci-4haloalkyl, C3-4cycloalkyl or C3-4cycloalkylCi-2alkyl.

In another embodiment R ³ is methyl, ethyl, / ^' so-propyl, ; ^' so-butyl, n-propyl, difluoromethyl, trifluoromethyl, CF3CH2-, CH3CF2-, FCH2CH2-, cyclopropyl, cyclobutyl or cyclopropyl-methyl-. Preferably R ³ is methyl, ethyl, / ^' so-propyl, / ^' so-butyl, difluoromethyl, trifluoromethyl, cyclopropyl or cyclopropyl- methyl-. More preferably, R ³ is methyl, ethyl, difluoromethyl or cyclopropyl.

R ⁴ is Ci-4alkyl, C2-4alkenyl, C2-4alkynyl, Ci-4haloalkyl, C2-4haloalkenyl, C2-4haloalkynyl or C3- 6cycloalkyl. Preferably, R ⁴ is Ci-4alkyl, Ci-4haloalkyl or C3-4cycloalkyl. More preferably, R ⁴ is Ci-4alkyl. Most preferably, R ⁴ is methyl or ethyl.

In one embodiment R ⁴ is Ci-4alkyl or C3-4cycloalkyl. Preferably, R ⁴ is methyl, ethyl or cyclopropyl. R ⁵ is hydrogen, d ealkyl, C2-6alkenyl, C2-6alkynyl, C-i ehaloalkyl, C2-6haloalkenyl, C2-6haloalkynyl,

Ci-4alkoxyCi-2alkyl-, Ci-4haloalkoxyCi-2alkyl-, C3-6cycloalkyl, Cs ehalocycloalkyl, C3-6cycloalkylCi-2alkyl-, C3-6cycloalkylC2-3alkenyl- or C3-6halocycloalkylCi-2alkyl-. Preferably, R ⁵ is d ealkyl, C2-6alkenyl, Ci- 6haloalkyl, C2-6haloalkenyl, C3-6cycloalkyl, C3-6cycloalkylCi-2alkyl-, C3-6cycloalkylC2-3alkenyl- or C3- 6halocycloalkylCi-2alkyl-. More preferably, R ⁵ is Ci ealkyl, C2-6alkenyl, C3-6cycloalkyl or C3-6cycloalkylCi- 2alkyl-. Even more preferably, R ⁵ is Ci-4alkyl, C2-4alkenyl or C3-4cycloalkylCi-2alkyl-. Even more preferably still, R ⁵ is methyl, ethyl, 2-methylprop-2-enyl or cyclopropyl-methyl-. Most preferably, R ⁵ is methyl.

In a further embodiment R ⁵ is Ci-4alkyl, C2-4alkenyl, C3-4cycloalkyl or C3-4cycloalkylCi-2alkyl-. Preferably, R ⁵ is methyl, ethyl, n-propyl, 2-methylprop-2-enyl, cyclopropyl or cyclopropyl-methyl-. More preferably, R ⁵ is methyl, ethyl, n-propyl or cyclopropyl.

R ⁶ is hydrogen, Ci-4alkyl, C2-4alkenyl, C2-4alkynyl, Ci-4haloalkyl, C2-4haloalkenyl, C2-4haloalkynyl, Ci-2alkoxyCi-2alkyl-, C3-6cycloalkyl or C3-6cycloalkylCi-2alkyl-. Preferably, R ⁶ is hydrogen, Ci-4alkyl, Ci- 4haloalkyl, C3-6cycloalkyl or C3-6cycloalkylCi-2alkyl-. More preferably, R ⁶ is hydrogen, Ci-4alkyl or C3- 6cycloalkylCi-2alkyl-. Even more preferably, R ⁶ is Ci-4alkyl. Most preferably, R ⁶ is methyl or ethyl.

In another embodiment R ⁶ is Ci-4alkyl, C2-4alkenyl, C2-4alkynyl, Ci-4haloalkyl, Ci-2alkoxyCi-2alkyl- , C3-6cycloalkyl or C3-6cycloalkylCi-2alkyl-. Preferably, R ⁶ is methyl, ethyl, ; ^' so-propyl, allyl, propargyl, CF3CH2-, CHF2CH2-, CH3OCH2CH2-, cyclopentyl or cyclopropyl-methyl-. More preferably, R ⁶ is methyl, ethyl or propargyl.

Preferably, in a compound according to formula (I) of the invention;

R is hydrogen or methyl;

R ² is halogen or Ci-4alkyl;

R ³ is Ci- ₄ alkyl;

R ⁴ is Ci- ₄ alkyl;

R ⁵ is Ci ealkyl, C2-6alkenyl, C3-6cycloalkyl or C3-6cycloalkylCi-2alkyl-; and

R ⁶ is Ci- ₄ alkyl.

In an alternative preferred embodiment of the invention; R is hydrogen or methyl;

R ² is halogen, Ci-4alkyl or C3-6cycloalkyl;

R ³ is Ci-4alkyl, Ci-4haloalkyl, C3-6cycloalkyl or C3-6cycloalkylCi-2alkyl;

R ⁴ is Ci-4alkyl or C3-4cycloalkyl;

R ⁵ is d ealkyl, C2-6alkenyl, C3-6cycloalkyl or C3-6cycloalkylCi-2alkyl-; and

R ⁶ is Ci-4alkyl, C2-4alkenyl, C2-4alkynyl, Ci-4haloalkyl, Ci-2alkoxyCi-2alkyl-, C3-6cycloalkyl or C3- 6cycloalkylCi-2alkyl-.

More preferably,

R is hydrogen;

R ² is bromo, methyl or ethyl;

R ³ is methyl or ethyl;

R ⁴ is methyl or ethyl;

R ⁵ is Ci-4alkyl, C2-4alkenyl or C3-4cycloalkylCi-2alkyl-; and

R ⁶ is methyl or ethyl.

In an alternative more preferred embodiment,

R is hydrogen;

R ² is bromo, chloro, methyl, ethyl or cyclopropyl;

R ³ is methyl, ethyl, / ^' so-propyl, / ^' so-butyl, n-propyl, difluoromethyl, trifluoromethyl, CF3CH2-,

CH3CF2-, FCH2CH2-, cyclopropyl, cyclobutyl or cyclopropyl-methyl-;

R ⁴ is methyl, ethyl or cyclopropyl;

R ⁵ is methyl, ethyl, n-propyl, 2-methylprop-2-enyl, cyclopropyl or cyclopropyl-methyl-; and R ⁶ is methyl, ethyl, / ^' so-propyl, allyl, propargyl, CF3CH2-, CHF2CH2-, CH3OCH2CH2-, cyclopentyl or cyclopropyl-methyl-.

Even more preferably,

R is hydrogen;

R ² is methyl;

R ³ is methyl or ethyl;

R ⁴ is methyl or ethyl;

R ⁵ is methyl, ethyl, 2-methylprop-2-enyl or cyclopropyl-methyl-; and

R ⁶ is methyl or ethyl. In an alternative even more preferred embodiment,

R is hydrogen;

R ² is methyl;

R ³ is methyl, ethyl, difluoromethyl or cyclopropyl;

R ⁴ is methyl or ethyl;

R ⁵ is methyl, ethyl, n-propyl or cyclopropyl; and

R ⁶ is methyl, ethyl or propargyl. In one embodiment, the compounds of formula (I) according to the invention may be useful for combating phytopathogenic fungi (e.g Alternaria alternata, Plasmopara viticola, Sclerotinia sclerotiorum or Septoria tritici also known as Mycosphaerella graminicola) containing a mutation in the mitochondrial cytochrome b gene conferring resistance to Qo inhibitors (e.g strobilurins such as azoxystrobin, pyraclostrobin and trifloxystrobin or fenamidone or famoxadon e).

In a further embodiment, the compounds of formula (I) according to the invention may be useful for combating phytopathogenic fungi (e.g Alternaria alternata, Plasmopara viticola, Sclerotinia sclerotiorum or Septoria tritici also known as Mycosphaerella graminicola) containing a mutation in the mitochondrial cytochrome b gene conferring resistance to Qo inhibitors (e.g strobilurins such as azoxystrobin, pyraclostrobin and trifloxystrobin or fenamidone or famoxadone), wherein the mutation is G143A. In another embodiment, the invention also relates to a method of controlling or preventing infestation of useful plants by phytopathogenic microorganisms (e.g Alternaria alternate, Plasmopara viticola, Sclerotinia sclerotiorum or Septoria tritici also known as Mycosphaerella graminicola), wherein the phytopathogenic microorganisms may contain a mutation in the mitochondrial cytochrome b gene conferring resistance to Qo inhibitors (e.g strobliurins such as azoxystrobin, pyraclostrobin and trifloxystrobin or fenamidone or famoxadone) and wherein a fungicidally effective amount of a 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.

The level of resistance and therefore the impact on the performance of the fungicide can be measured by the use of a 'Resistance Factor' (RF). The resistance factor can be calculated by dividing the concentration of a fungicide that provides a set level of disease control (i.e. 50 percent) for the 'resistant' fungal strain with the concentration of the same fungicide that provides the same level of disease control for the 'susceptible' strain of the same fungal species (RF = EC50 value of the resistant strain/EC50 value of the sensitive strain). Although there are no set rules, three categories can be defined: 1 ) RF > 50 = resistant strain, 2) 5≤ RF < 50 = less sensitive strain (shift in sensitivity), and 3) RF < 5 = sensitive strain.

In order to obtain resistant fungal strains, a researcher is to locate a host crop and geographical region where the relevant resistance had been reported in literature. Leaf samples infected by the target disease are then collected from the locations/host crops and sent to a laboratory, where pure cultures would be isolated. The resistant phenotype of the fungal cultures is determined either by conducting a full dose response bioassay and comparing the bioassay results to similar bioassay results for a known susceptible strain of the same species. Alternatively the resistance genotype of the fungal strain can be determined by molecular techniques (e.g. qPCR) if the resistance mechanism for the relevant species is known. Compounds of formula (I) can be prepared by reaction of compounds of formula (II), wherein R R ² and are as defined for compounds of formula (I) with compounds of formula (III), wherein R ³ , R ⁴ , R ⁵ and R ⁶ are as defined for compounds of formula (I) in a suitable solvent (e.g. DMF, toluene, tetrahydrofuran or dioxane) at a temperature between 25°C and 1 10°C, optionally in the presence of an organic or inorganic base (eg, NaH, NaO'Bu, triethylamine or K2CO3). This reaction is shown in Scheme 1.

(II) (HI)

(I)

Scheme 1

Compounds of formula (II) wherein R and R ² are as defined for compounds of formula (I) and Hal is a halogen atom (eg, bromo) can be prepared by reacting a compound of formula (IV), wherein R and R ² are as defined for compounds of formula (I), with a halogenating agent (eg, bromine, chlorine, iodine, N-chlorosuccinimide, N-bromosuccinimide, 1 ,3-dibromo-5,5-dimethylhydantoin), in the presence of a radical initiator (eg, benzoyl peroxide, azobisisobutyronitrile), in a suitable solvent (eg, hexane, benzene, carbontetrachloride), at temperature ranging from room temperature up to the solvent boiling point. This is shown in scheme 2.

Scheme 2

It is recommended to perform this transformation on compounds wherein R and R ² are not Ci- 4alkyl or C3-6cycloalkyl to avoid formation of side products poly-halogenated. However, it should also be understood that a person skilled in the art could manage to isolate the desired compounds of formula (II) from mixtures of mono- and poly-halogenated compounds would that be required. Alternatively, the Ci-4alkyl or Cs ecycloalkyl groups can be introduced by standard transformations such as metal mediated cross-coupling reactions starting from compounds where R ² is chloro, bromo or iodo. There are no particular limitations on the coupling agent, catalyst, solvent and bases, provided it is used in ordinary coupling reactions, such as those described in "Cross-Coupling Reactions: A Practical Guide (Topics in Current Chemistry)", edited by Norio Miyaura and S.L. Buchwald (editions Springer), or "Metal- Catalyzed Cross-Coupling Reactions", edited by Armin de Meijere and Frangois Diederich (editions WILEY-VCH).

Compounds of formula (IV) wherein R and R ² are as defined for compounds of formula (I) can be prepared by alkylation of a compound of formula (V), wherein R and R ² are as defined for compounds of formula (I), with methyl iodide and a base (eg, K2CO3, NaH) in a suitable solvent (eg, tetrahydrofuran, Ν,Ν-dimethylformamide, acetone). This is shown in scheme 3.

(V) (IV)

Scheme 3 Compounds of formula (V) wherein R and R ² are as defined for compounds of formula (I) can be prepared by azidation of a compound of formula (VI), wherein R and R ² are as defined for compounds of formula (I), in a suitable solvent (eg, toluene, hexane, 1 ,2-dichloroethane) or neat. Examples of azidating agents include inorganic azides such as sodium azide and organic azides such as trimethylsilyl azide and diphenylphosphorylazide. If necessary a Lewis acid such as aluminum trichloride or zinc chloride may be added to the reaction. This is shown in scheme 4. Similar transformations have been described in the literature.

(VI) (V)

Scheme 4 _

12

Isocyanates of formula (VI), wherein R and R ² are as defined for compounds of formula (I), can be prepared from the corresponding aniline (VII), wherein R and R ² are as defined for compounds of formula (I), in the presence of an isocyanating agent such as phosgene or carbonyldiimidazole. Alternatively they can be prepared from the carboxylic acid derivatives (VIII), wherein R and R ² are as defined for compounds of formula (I), using methods know to a person skilled in the art. This is shown in scheme 5. Among the various protocols reported for the transformation of acids to isocyanates (VI), the following have found wide spread application:

1 ) Treatment of acids (VIII) with diphenylphosphoryl azide and an amine base such as tributylamine in an inert organic solvent such as toluene at temperatures between 50 °C and 120 °C to give isocyanate (VI) as described in /At/si. J. Chem., 1973, 1591-3.

2) Treatment of acids (VIII) with an activating agent, such as thionyl chloride or propylphosphonic anhydride, in the presence of an azide source, such as sodium azide, and an organic base, such as triethyl amine, in an inert solvent, such as tetrahydrofuran, at temperatures between 20 °C and 100 °C as described in Synthesis 201 1 , 1477-1483.

3) Conversion of acids (VIII) to the corresponding hydroxamic acid which can then be treated with a dehydrating agent, such as para-toluenesulfonyl chloride, and a base, such as trimethylamine, in an inert organic solvent, such as toluene, at temperatures between 20 °C and 120 °C.

Scheme 5

Compounds of formula (III), wherein R ³ , R ⁴ , R ⁵ and R ⁶ are as defined for compounds of formula (I), can be prepared by the reaction of compounds of formula (IX), wherein R ⁴ , R ⁵ and R ⁶ are as defined for compounds of formula (I), with hydrazides of formula (X),wherein R ³ is as defined for compounds of formula (I), in a suitable solvent (e.g. DMF, ethanol, toluene or tetrahydrofuran) at a temperature between 25°C and 1 10°C, optionally in the presence of an organic or inorganic base (eg, triethylamine or K2CO3). In some cases, a better reaction performance may be gained from the use of an acid catalyst (eg, acetic acid) or a dehydrating agent (eg, MgSC ). This reaction is shown in Scheme 6.

Scheme 6

Alternatively, compounds of formula (III), wherein R ³ , R ⁴ , R ⁵ and R ⁶ are as defined for compounds of formula (I), can be prepared by reaction of compounds of formula (XI), wherein R ⁴ , R ⁵ and R ⁶ are as defined for compounds of formula (I), with an acid chloride of formula (XII), wherein R ³ is as defined for compounds of formula (I), in a suitable solvent (e.g. toluene, tetrahydrofuran or pyridine) at a temperature between 25°C and 1 10°C, optionally in the presence of an organic or inorganic base (eg, triethylamine or K2CO3). In some cases, a better reaction performance may be gained from the use of dimethylaminopyridine. This reaction is shown in Scheme 7.

Scheme 7

Compounds of formula (XI), wherein R ⁴ , R ⁵ and R ⁶ are as defined for compounds of formula (I), can be prepared by reaction of compounds of formula (IX) wherein R ⁴ , R ⁵ and R ⁶ are as defined for compounds of formula (I), with hydrazine, one of its acid addition salts, or its hydrate, in a suitable solvent (e.g. water, methanol, ethanol, toluene, tetrahydrofuran or pyridine) at a temperature between 25°C and 1 10°C, optionally in the presence of an organic or inorganic base (eg, triethylamine or K2CO3). In some cases, a better reaction performance may be gained from the use of an acid catalyst (eg, acetic acid) or a dehydrating agent (eg, MgSC ). This reaction is shown in Scheme 8

Compounds of formula (IX), wherein R ⁴ , R ⁵ and R ⁶ are as defined for compounds of formula (I), can be obtained by alkylation of an oxime (IX-a), wherein R ⁴ and R ⁵ are as defined for compounds of formula (I), using an alkylating reagent of formula (XIII), wherein R ⁶ is as defined for compounds of formula (I) and LG is a leaving group such as halogen (eg, bromo, iodo) or a suitable sulphonate derivative (eg, methyl sulphonate), in the presence of a suitable base (eg, NaH, K2CO3, triethylamine). This reaction is shown in Scheme 9.

Scheme 9 It should be recognised that compounds of formula (IX-a), wherein R ⁴ and R ⁵ are as defined for compounds of formula (I), can be prepared by reaction of a compound of formula (XIV), wherein R ⁴ and R ⁵ are as defined for compounds of formula (I), using nitrous acid or its salts (eg, NaNCh) or alkyl nitrites (eg, isopentyl nitrite) in the presence of an acid (eg, HCI) or base (eg, NaH, LDA, K2CO3) in a suitable solvent at temperature from -20°C to 80°C. This reaction is shown in Scheme 10. H

(XIV) (IX-a)

Scheme 10

Alternatively compounds of formula (IX-a), wherein R ⁴ and R ⁵ are as defined for compounds of formula (I), can be obtained from a compound of formula (XV), wherein R ⁴ and R ⁵ are as defined for compounds of formula (I) and R ^c is Ci-e-alkyl, via decarboxylase oximation using a base and a nitrous acid salt or an alkyl nitrite, followed by treatment with an acid, at temperatures that range from -20°C to 80°C. This reaction is shown in Scheme 1 1.

(XV) (IX-a)

Scheme 1 1

Compounds of formula (XIV) and (XV), wherein R ⁴ and R ⁵ are as defined for compounds of formula (I), are prepared by known methods or are commercially available. Functional group interconversions as described in the previous schemes are known to the persons skilled in the art. Extensive lists of reaction conditions can be found in: Comprehensive Organic Functional Group Transformations, Edited by A. R. Katritzky, O. Meth-Cohn and C. W. Rees. Pergamon Press (Elsevier Science Ltd.), Tarrytown, NY. 1995; or in: Comprehensive Organic Transformations: A Guide to Functional Group Preparations, Edited by Richard C. Larock, Wiley-VCH, New York 1999.

If the synthesis yields mixtures of isomers in the case of oximes or hydrazones, a separation is generally not necessarily required because in some cases the individual isomers can be interconverted during work-up for use or during application (e. g. under the action of light, acids or bases). Such conversions may also take place after use, e. g. in the treatment of plants in the treated plant, or in the harmful fungus to be controlled. The skilled person would understand that a compound of formula (I) can be drawn to represent such a mixture of isomers as shown below for a compound of formula (l-x).

(l-x)

In a compound of formula (l-x) the crossed bonds indicate that the substituted imines and oxime may be present in E or Z form or as mixtures of both in any proportion.

As already indicated, it has now been found that the novel compounds of Formula (I) of the present invention have 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 the 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 can 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 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" where used 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 may also be possible to use compounds of formula (I) as dressing agents for the treatment of plant propagation material, e.g., seed, such as fruits, tubers or grains, or plant cuttings, 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: seed, for example, can be dressed before being sown. The active compounds of formula (I) 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, for example, 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 of formula (I) 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) are 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.

The compounds of formula (I) may be used for example on turf, ornamentals, such as flowers, shrubs, broad-leaved trees or evergreens, for example conifers, as well as for tree injection, pest management and the like.

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 also including 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 also including 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 CrylllB(bl ) 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 (Bt11 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 δ-endotoxins, e.g. CrylAb, CrylAc, Cryl 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.

Further, in the context of the present invention there are to be understood by δ-endotoxins, for example CrylAb, CrylAc, Cryl 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, WO93/07278, W095/34656, 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 CrylAc toxin); Bollgard II® (cotton variety that expresses a CrylAc 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 * 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 * 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 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 can 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 can be protected before transplantation by a total or partial treatment by immersion. Preferably "plant propagation material" is understood to denote seeds.

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.

Suspension concentrates are aqueous formulations in which finely divided solid particles of the active compound are suspended. Such formulations include anti-settling agents and dispersing agents and may further include a wetting agent to enhance activity as well an anti-foam and a crystal growth inhibitor. In use, these concentrates are diluted in water and normally applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.

Wettable powders are in the form of finely divided particles which disperse readily in water or 5 other liquid carriers. The particles contain the active ingredient retained in a solid matrix. Typical solid matrices include fuller's earth, kaolin clays, silicas and other readily wet organic or inorganic solids. Wettable powders normally contain from 5% to 95% of the active ingredient plus a small amount of wetting, dispersing or emulsifying agent.

Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other 10 liquid and may consist entirely of the active compound with a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isophorone and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquid and normally applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.

15 Granular formulations include both extrudates and relatively coarse particles and are usually applied without dilution to the area in which treatment is required. Typical carriers for granular formulations include sand, fuller's earth, attapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, ground corn cobs, ground peanut hulls, sugars, sodium chloride, sodium sulphate, sodium silicate,

20 sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulphate and other organic or inorganic materials which absorb or which can be coated with the active compound. Granular formulations normally contain 5% to 25% of active ingredients which may include surface-active agents such as heavy aromatic naphthas, kerosene and other petroleum fractions, or vegetable oils; and/or stickers such as dextrins, glue or synthetic resins.

25 Dusts are free-flowing admixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids which act as dispersants and carriers.

Microcapsules are typically droplets or granules of the active ingredient enclosed in an inert porous shell which allows escape of the enclosed material to the surroundings at controlled rates. Encapsulated droplets are typically 1 to 50 microns in diameter. The enclosed liquid typically constitutes

30 50 to 95% of the weight of the capsule and may include solvent in addition to the active compound.

Encapsulated granules are generally porous granules with porous membranes sealing the granule pore openings, retaining the active species in liquid form inside the granule pores. Granules typically range from 1 millimetre to 1 centimetre and preferably 1 to 2 millimetres in diameter. Granules are formed by extrusion, agglomeration or prilling, or are naturally occurring. Examples of such materials are

35 vermiculite, sintered clay, kaolin, attapulgite clay, sawdust and granular carbon. Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.

Other useful formulations for agrochemical applications include simple solutions of the active 40 ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene and other organic solvents. Pressurised sprayers, wherein the active ingredient is dispersed in finely-divided form as a result of vaporisation of a low boiling dispersant solvent carrier, may also be used.

Suitable agricultural adjuvants and carriers that are useful in formulating the compositions of the invention in the formulation types described above are well known to those skilled in the art.

Liquid carriers that can be employed include, for example, water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetonalcohol, 1 ,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, Ν,Ν-dimethyl formamide, dimethyl sulfoxide, 1 ,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkyl pyrrolidinone, ethyl acetate, 2-ethyl hexanol, ethylene carbonate, 1 ,1 ,1-trichloroethane, 2-heptanone, alpha pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol diacetate, glycerol monoacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropyl benzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxy-propanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octyl amine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol, and higher molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, etc., ethylene glycol, propylene glycol, glycerine and N-methyl-2-pyrrolidinone. Water is generally the carrier of choice for the dilution of concentrates.

Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, diatomaxeous earth, lime, calcium carbonate, bentonite clay, fuller's earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour and lignin.

A broad range of surface-active agents are advantageously employed in both said liquid and solid compositions, especially those designed to be diluted with carrier before application. These agents, when used, normally comprise from 0.1 % to 15% by weight of the formulation. They can be anionic, cationic, non-ionic or polymeric in character and can be employed as emulsifying agents, wetting agents, suspending agents or for other purposes. Typical surface active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulphate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C.sub. 18 ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-C.sub. 16 ethoxylate; soaps, such as sodium stearate; alkylnaphthalenesulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyi esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono and dialkyi phosphate esters. Other adjuvants commonly utilized in agricultural compositions include crystallisation inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, anti-foaming agents, light-blocking agents, compatibilizing agents, antifoam agents, sequestering agents, neutralising agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, emollients, lubricants and sticking agents.

In addition, further, other biocidally active ingredients or compositions may be combined with the compositions of the invention and used in the methods of the invention and applied simultaneously or sequentially with the compositions of the invention. When applied simultaneously, these further active ingredients may be formulated together with the compositions of the invention or mixed in, for example, the spray tank. These further biocidally active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and/or plant growth regulators.

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

In addition, the compositions of the invention may also be applied with one or more systemically acquired resistance inducers ("SAR" inducer). SAR inducers are known and described in, for example, United States Patent No. US 6,919,298 and include, for example, salicylates and the commercial SAR inducer acibenzolar-S-methyl.

The compounds of formula (I) are normally used in the form of agrochemical 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 nonselective 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 defined herein, in free form or in agrochemically usable salt form, and at least one of the above-mentioned adjuvants.

The invention therefore 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, sulfonamide 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)-me thanone, (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)-m ethoxyimino]-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,N - dimethyl-5-p-tolylimidazole-1 -sulfonamide, N-allyl-4, 5,-dimethyl-

2- trimethylsilylthiophene-3-carboxamide, N- (l-cyano-1 , 2-d i m ethyl p ropy I )-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-ieri-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-met hoxyacrylate, methyl (E)-2-[2-[6-(2,6-difluorophenoxy)pyrimidin-4-yloxy]phenyl]-3 -methoxyacryla te, 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-methoxyacrylat e, 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-methoxyac rylate, 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-ieri-butyl-pyridin-2-yloxy)phenyl]-3-methoxyacry late, 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-methoxy acrylate, methyl (E)-2-[2-[6-(2-chloropyridin-3-yloxy)pyrimidin-4-yloxy]pheny l]-3-methoxyac rylate, methyl (E),(E)-2-[2- (5,6-dimethylpyrazin-2-ylmethyloximinomethyl)phenyl]-3-metho x yacrylate, methyl (E)-2-{2-[6-(6- methylpyridin-2-yloxy)pyrimidin-4-yloxy]phenyl}-3-methoxy-a 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-methox yacrylate, methyl (E),(E)-2-{2-[(4-chlorophenyl)- methyloximinomethyl]-phenyl}-3-methoxyacryl ate, methyl (E)-2-{2-[6-(2-n-propylphenoxy)-1 ,3,5- triazin-4-yloxy]phenyl}-3-methoxyacr ylate, 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, 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)^-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, hexa chlorobenzene, 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, LY211795, 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, paclobutrazol, 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 96/15121 and also with anthelmintic active cyclic depsipeptides such as those described in WO 96/11945, WO 93/19053, WO 93/25543, EP 0 626 375, EP 0 382 173, WO 94/19334, EP 0 382 173, and EP 0 503 538.

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 International Patent Application Publication Numbers 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, thiabendazole.

The following mixtures of the compounds of formula (I) with active ingredients are preferred. The abbreviation "TX" means one compound selected from the group consisting of the compounds described in Tables 1 .1 to 1.19 (below) or Table A (compounds A-1 to A-63) (below). an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628) + TX,

an acaricide selected from the group of substances consisting of 1 , 1-bis(4-chlorophenyl)-2- ethoxyethanol (lUPAC name) (910) + TX, 2,4-dichlorophenyl benzenesulfonate (lUPAC/Chemical Abstracts name) (1059) + TX, 2-fluoro-A/-methyl-A/-1-naphthylacetamide (lUPAC name) (1295) + TX, 4- chlorophenyl phenyl sulfone (lUPAC name) (981 ) + TX, abamectin (1 ) + TX, acequinocyl (3) + TX, acetoprole [CCN] + TX, acrinathrin (9) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, alpha- cypermethrin (202) + TX, amidithion (870) + TX, amidoflumet [CCN] + TX, amidothioate (872) + TX, amiton (875) + TX, amiton hydrogen oxalate (875) + TX, amitraz (24) + TX, aramite (881 ) + TX, arsenous oxide (882) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, azobenzene (lUPAC name) (888) + TX, azocyclotin (46) + TX, azothoate (889) + TX, benomyl (62) + TX, benoxafos (alternative name) [CCN] + TX, benzoximate (71 ) + TX, benzyl benzoate (lUPAC name) [CCN] + TX, bifenazate (74) + TX, bifenthrin (76) + TX, binapacryl (907) + TX, brofenvalerate (alternative name) + TX, bromocyclen (918) + TX, bromophos (920) + TX, bromophos-ethyl (921 ) + TX, bromopropylate (94) + TX, buprofezin (99) + TX, butocarboxim (103) + TX, butoxycarboxim (104) + TX, butylpyridaben (alternative name) + TX, calcium polysulfide (lUPAC name) (1 1 1 ) + TX, camphechlor (941 ) + TX, carbanolate (943) + TX, carbaryl (1 15) + TX, carbofuran (1 18) + TX, carbophenothion (947) + TX, CGA 50'439 (development code) (125) + TX, chinomethionat (126) + TX, chlorbenside (959) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorfenapyr (130) + TX, chlorfenethol (968) + TX, chlorfenson (970) + TX, chlorfensulfide (971 ) + TX, chlorfenvinphos (131 ) + TX, chlorobenzilate (975) + TX, chloromebuform (977) + TX, chloromethiuron (978) + TX, chloropropylate (983) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX, chlorthiophos (994) + TX, cinerin I (696) + TX, cinerin II (696) + TX, cinerins (696) + TX, clofentezine (158) + TX, closantel (alternative name) [CCN] + TX, coumaphos (174) + TX, crotamiton (alternative name) [CCN] + TX, crotoxyphos (1010) + TX, cufraneb (1013) + TX, cyanthoate (1020) + TX, cyflumetofen (CAS Reg. No.: 400882-07-7) + TX, cyhalothrin (196) + TX, cyhexatin (199) + TX, cypermethrin (201 ) + TX, DCPM (1032) + TX, DDT (219) + TX, demephion (1037) + TX, demephion-0 (1037) + TX, demephion-S (1037) + TX, demeton (1038) + TX, demeton-methyl (224) + TX, demeton- O (1038) + TX, demeton-O-methyl (224) + TX, demeton-S (1038) + TX, demeton-S-methyl (224) + TX, demeton-S-methylsulfon (1039) + TX, diafenthiuron (226) + TX, dialifos (1042) + TX, diazinon (227) + TX, dichlofluanid (230) + TX, dichlorvos (236) + TX, dicliphos (alternative name) + TX, dicofol (242) + TX, dicrotophos (243) + TX, dienochlor (1071 ) + TX, dimefox (1081 ) + TX, dimethoate (262) + TX, dinactin (alternative name) (653) + TX, dinex (1089) + TX, dinex-diclexine (1089) + TX, dinobuton (269) + TX, dinocap (270) + TX, dinocap-4 [CCN] + TX, dinocap-6 [CCN] + TX, dinocton (1090) + TX, dino- penton (1092) + TX, dinosulfon (1097) + TX, dinoterbon (1098) + TX, dioxathion (1 102) + TX, diphenyl sulfone (lUPAC name) (1 103) + TX, disulfiram (alternative name) [CCN] + TX, disulfoton (278) + TX, DNOC (282) + TX, dofenapyn (1 1 13) + TX, doramectin (alternative name) [CCN] + TX, endosulfan (294) + TX, endothion (1 121 ) + TX, EPN (297) + TX, eprinomectin (alternative name) [CCN] + TX, ethion (309) + TX, ethoate-methyl (1 134) + TX, etoxazole (320) + TX, etrimfos (1 142) + TX, fenazaflor (1 147) + TX, fenazaquin (328) + TX, fenbutatin oxide (330) + TX, fenothiocarb (337) + TX, fenpropathrin (342) + TX, fenpyrad (alternative name) + TX, fenpyroximate (345) + TX, fenson (1 157) + TX, fentrifanil (1 161 ) + TX, fenvalerate (349) + TX, fipronil (354) + TX, fluacrypyrim (360) + TX, fluazuron (1 166) + TX, flubenzimine (1 167) + TX, flucycloxuron (366) + TX, flucythrinate (367) + TX, fluenetil (1 169) + TX, flufenoxuron (370) + TX, flumethrin (372) + TX, fluorbenside (1 174) + TX, fluvalinate (1 184) + TX, FMC 1 137 (development code) (1 185) + TX, formetanate (405) + TX, formetanate hydrochloride (405) + TX, formothion (1 192) + TX, formparanate (1 193) + TX, gamma-HCH (430) + TX, glyodin (1205) + TX, halfenprox (424) + TX, heptenophos (432) + TX, hexadecyl cyclopropanecarboxylate (lUPAC/Chemical Abstracts name) (1216) + TX, hexythiazox (441 ) + TX, iodomethane (lUPAC name) (542) + TX, isocarbophos (alternative name) (473) + TX, isopropyl 0-(methoxyaminothiophosphoryl)salicylate (lUPAC name) (473) + TX, ivermectin (alternative name) [CCN] + TX, jasmolin I (696) + TX, jasmolin II (696) + TX, jodfenphos (1248) + TX, lindane (430) + TX, lufenuron (490) + TX, malathion (492) + TX, malonoben (1254) + TX, mecarbam (502) + TX, mephosfolan (1261 ) + TX, mesulfen (alternative name) [CCN] + TX, methacrifos (1266) + TX, methamidophos (527) + TX, methidathion (529) + TX, methiocarb (530) + TX, methomyl (531 ) + TX, methyl bromide (537) + TX, metolcarb (550) + TX, mevinphos (556) + TX, mexacarbate (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafox (1293) + TX, monocrotophos (561 ) + TX, morphothion (1300) + TX, moxidectin (alternative name) [CCN] + TX, naled (567) + TX, NC-184 (compound code) + TX, NC-512 (compound code) + TX, nifluridide (1309) + TX, nikkomycins (alternative name) [CCN] + TX, nitrilacarb (1313) + TX, nitrilacarb 1 : 1 zinc chloride complex (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, omethoate (594) + TX, oxamyl (602) + TX, oxydeprofos (1324) + TX, oxydisulfoton (1325) + TX, pp'-DDT (219) + TX, parathion (615) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, phenkapton (1330) + TX, phenthoate (631 ) + TX, phorate (636) + TX, phosalone (637) + TX, phosfolan (1338) + TX, phosmet (638) + TX, phosphamidon (639) + TX, phoxim (642) + TX, pirimiphos-methyl (652) + TX, polychloroterpenes (traditional name) (1347) + TX, polynactins (alternative name) (653) + TX, proclonol (1350) + TX, profenofos (662) + TX, promacyl (1354) + TX, propargite (671 ) + TX, propetamphos (673) + TX, propoxur (678) + TX, prothidathion (1360) + TX, prothoate (1362) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyridaphenthion (701 ) + TX, pyrimidifen (706) + TX, pyrimitate (1370) + TX, quinalphos (71 1 ) + TX, quintiofos (1381 ) + TX, R-1492 (development code) (1382) + TX, RA-17 (development code) (1383) + TX, rotenone (722) + TX, schradan (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, sophamide (1402) + TX, spirodiclofen (738) + TX, spiromesifen (739) + TX, SSI-121 (development code) (1404) + TX, sulfiram (alternative name) [CCN] + TX, sulfluramid (750) + TX, sulfotep (753) + TX, sulfur (754) + TX, SZI-121 (development code) (757) + TX, tau-fluvalinate (398) + TX, tebufenpyrad (763) + TX, TEPP (1417) + TX, terbam (alternative name) + TX, tetrachlorvinphos (777) + TX, tetradifon (786) + TX, tetranactin (alternative name) (653) + TX, tetrasul (1425) + TX, thiafenox (alternative name) + TX, thiocarboxime (1431 ) + TX, thiofanox (800) + TX, thiometon (801 ) + TX, thioquinox (1436) + TX, thuringiensin (alternative name) [CCN] + TX, triamiphos (1441 ) + TX, triarathene (1443) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, trichlorfon (824) + TX, trifenofos (1455) + TX, trinactin (alternative name) (653) + TX, vamidothion (847) + TX, vaniliprole [CCN] and YI-5302 (compound code) + TX,

an algicide selected from the group of substances consisting of bethoxazin [CCN] + TX, copper dioctanoate (lUPAC name) (170) + TX, copper sulfate (172) + TX, cybutryne [CCN] + TX, dichlone (1052) + TX, dichlorophen (232) + TX, endothal (295) + TX, fentin (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamid (1379) + TX, simazine (730) + TX, triphenyltin acetate (lUPAC name) (347) and triphenyltin hydroxide (lUPAC name) (347) + TX, an anthelmintic selected from the group of substances consisting of abamectin (1 ) + TX, crufomate (101 1 ) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291 ) + TX, emamectin benzoate (291 ) + TX, eprinomectin (alternative name) [CCN] + TX, ivermectin (alternative name) [CCN] + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, piperazine [CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) and thiophanate (1435) + TX,

an avicide selected from the group of substances consisting of chloralose (127) + TX, endrin (1 122) + TX, fenthion (346) + TX, pyridin-4-amine (lUPAC name) (23) and strychnine (745) + TX, a bactericide selected from the group of substances consisting of 1 -hydroxy- 1 - -pyridi ne-2- thione (lUPAC name) (1222) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (lUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (lUPAC name) (170) + TX, copper hydroxide (lUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophen (232) + TX, dipyrithione (1 105) + TX, dodicin (1 1 12) + TX, fenaminosulf (1 144) + TX, formaldehyde (404) + TX, hydrargaphen (alternative name) [CCN] + TX, kasugamycin (483) + TX, kasugamycin hydrochloride hydrate (483) + TX, nickel bis(dimethyldithiocarbamate) (lUPAC name) (1308) + TX, nitrapyrin (580) + TX, octhilinone (590) + TX, oxolinic acid (606) + TX, oxytetracycline (61 1 ) + TX, potassium hydroxyquinoline sulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, streptomycin sesquisulfate (744) + TX, tecloftalam (766) + TX, and thiomersal (alternative name) [CCN] + TX,

a biological agent selected from the group of substances consisting of Adoxophyes orana GV (alternative name) (12) + TX, Agrobacterium radiobacter (alternative name) (13) + TX, Amblyseius spp. (alternative name) (19) + TX, Anagrapha falcifera NPV (alternative name) (28) + TX, Anagrus atomus (alternative name) (29) + TX, Aphelinus abdominalis (alternative name) (33) + TX, Aphidius colemani (alternative name) (34) + TX, Aphidoletes aphidimyza (alternative name) (35) + TX, Autographa californica NPV (alternative name) (38) + TX, Bacillus firmus (alternative name) (48) + TX, Bacillus sphaericus Neide (scientific name) (49) + TX, Bacillus thuringiensis Berliner (scientific name) (51 ) + TX, Bacillus thuringiensis subsp. aizawai (scientific name) (51 ) + TX, Bacillus thuringiensis subsp. israelensis (scientific name) (51 ) + TX, Bacillus thuringiensis subsp. japonensis (scientific name) (51 ) + TX, Bacillus thuringiensis subsp. kurstaki (scientific name) (51 ) + TX, Bacillus thuringiensis subsp. tenebrionis (scientific name) (51 ) + TX, Beauveria bassiana (alternative name) (53) + TX, Beauveria brongniartii (alternative name) (54) + TX, Chrysoperla carnea (alternative name) (151 ) + TX, Cryptolaemus montrouzieri (alternative name) (178) + TX, Cydia pomonella GV (alternative name) (191 ) + TX, Dacnusa sibirica (alternative name) (212) + TX, Diglyphus isaea (alternative name) (254) + TX, Encarsia formosa (scientific name) (293) + TX, Eretmocerus eremicus (alternative name) (300) + TX, Helicoverpa zea NPV (alternative name) (431 ) + TX, Heterorhabditis bacteriophora and H. megidis (alternative name) (433) + TX, Hippodamia convergens (alternative name) (442) + TX, Leptomastix dactylopii (alternative name) (488) + TX, Macrolophus caliginosus (alternative name) (491 ) + TX, Mamestra brassicae NPV (alternative name) (494) + TX, Metaphycus helvolus (alternative name) (522) + TX, Metarhizium anisopliae var. acridum (scientific name) (523) + TX, Metarhizium anisopliae var. anisopliae (scientific name) (523) + TX, Neodiprion sertifer NPV and N. lecontei NPV (alternative name) (575) + TX, Orius spp. (alternative name) (596) + TX, Paecilomyces fumosoroseus (alternative name) (613) + TX, Phytoseiulus persimilis (alternative name) (644) + TX, Spodoptera exigua multicapsid nuclear polyhedrosis virus (scientific name) (741 ) + TX, Steinemema bibionis (alternative name) (742) + TX, Steinemema carpocapsae (alternative name) (742) + TX, Steinemema feltiae (alternative name) (742) + TX, Steinemema glaseri (alternative name) (742) + TX, Steinemema riobrave (alternative name) (742) + TX, Steinemema riobravis (alternative name) (742) + TX, Steinemema scapterisci (alternative name) (742) + TX, Steinemema spp. (alternative name) (742) + TX, Trichogramma spp. (alternative name) (826) + TX, Typhlodromus occidentalis (alternative name) (844) and Verticillium lecanii (alternative name) (848) + TX, bacillus subtilis var. amyloliquefaciens Strain FZB24 (available from Novozymes Biologicals Inc., 5400 Corporate Circle, Salem, VA 24153, U.S.A. and known under the trade name Taegro®) + TX,

a soil sterilant selected from the group of substances consisting of iodomethane (lUPAC name)

(542) and methyl bromide (537) + TX,

a chemosterilant selected from the group of substances consisting of apholate [CCN] + TX, bisazir (alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, diflubenzuron (250) + TX, dimatif (alternative name) [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, methiotepa [CCN] + TX, methyl apholate [CCN] + TX, morzid [CCN] + TX, penfluron (alternative name) [CCN] + TX, tepa [CCN] + TX, thiohempa (alternative name) [CCN] + TX, thiotepa (alternative name) [CCN] + TX, tretamine (alternative name) [CCN] and uredepa (alternative name) [CCN] + TX,

an insect pheromone selected from the group of substances consisting of (E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol (lUPAC name) (222) + TX, (E)-tridec-4-en-1-yl acetate (lUPAC name) (829) + TX, (E)-6-methylhept-2-en-4-ol (lUPAC name) (541 ) + TX, (E,Z)-tetradeca-4, 10-dien-1-yl acetate (lUPAC name) (779) + TX, (Z)-dodec-7-en-1-yl acetate (lUPAC name) (285) + TX, (Z)-hexadec- 1 1-enal (lUPAC name) (436) + TX, (Z)-hexadec-l 1-en-1-yl acetate (lUPAC name) (437) + TX, (Z)- hexadec-13-en-1 1-yn-1-yl acetate (lUPAC name) (438) + TX, (Z)-icos-13-en-10-one (lUPAC name) (448) + TX, (Z)-tetradec-7-en-1-al (lUPAC name) (782) + TX, (Z)-tetradec-9-en-1-ol (lUPAC name) (783) + TX, (Z)-tetradec-9-en-1-yl acetate (lUPAC name) (784) + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate (lUPAC name) (283) + TX, (9Z, 1 1 E)-tetradeca-9, 1 1-dien-1-yl acetate (lUPAC name) (780) + TX, (9Z, 12E)-tetradeca-9, 12-dien-1-yl acetate (lUPAC name) (781 ) + TX, 14-methyloctadec-1-ene (lUPAC name) (545) + TX, 4-methylnonan-5-ol with 4-methylnonan-5-one (lUPAC name) (544) + TX, alpha- multistriatin (alternative name) [CCN] + TX, brevicomin (alternative name) [CCN] + TX, codlelure (alternative name) [CCN] + TX, codlemone (alternative name) (167) + TX, cuelure (alternative name) (179) + TX, disparlure (277) + TX, dodec-8-en-1-yl acetate (lUPAC name) (286) + TX, dodec-9-en-1-yl acetate (lUPAC name) (287) + TX, dodeca-8 + TX, 10-dien-1-yl acetate (lUPAC name) (284) + TX, dominicalure (alternative name) [CCN] + TX, ethyl 4-methyloctanoate (lUPAC name) (317) + TX, eugenol (alternative name) [CCN] + TX, frontalin (alternative name) [CCN] + TX, gossyplure (alternative name) (420) + TX, grandlure (421 ) + TX, grandlure I (alternative name) (421 ) + TX, grandlure II (alternative name) (421 ) + TX, grandlure III (alternative name) (421 ) + TX, grandlure IV (alternative name) (421 ) + TX, hexalure [CCN] + TX, ipsdienol (alternative name) [CCN] + TX, ipsenol (alternative name) [CCN] + TX, japonilure (alternative name) (481 ) + TX, lineatin (alternative name) [CCN] + TX, litlure (alternative name) [CCN] + TX, looplure (alternative name) [CCN] + TX, medlure [CCN] + TX, megatomoic acid (alternative name) [CCN] + TX, methyl eugenol (alternative name) (540) + TX, muscalure (563) + TX, octadeca-2, 13-dien-1-yl acetate (lUPAC name) (588) + TX, octadeca-3, 13-dien- 1-yl acetate (lUPAC name) (589) + TX, orfralure (alternative name) [CCN] + TX, oryctalure (alternative name) (317) + TX, ostramone (alternative name) [CCN] + TX, siglure [CCN] + TX, sordidin (alternative name) (736) + TX, sulcatol (alternative name) [CCN] + TX, tetradec-1 1-en-1-yl acetate (lUPAC name) (785) + TX, trimedlure (839) + TX, trimedlure A (alternative name) (839) + TX, trimedlure Bi (alternative name) (839) + TX, trimedlure B2 (alternative name) (839) + TX, trimedlure C (alternative name) (839) and trunc-call (alternative name) [CCN] + TX,

an insect repellent selected from the group of substances consisting of 2-(octylthio)ethanol (lUPAC name) (591 ) + TX, butopyronoxyl (933) + TX, butoxy(polypropylene glycol) (936) + TX, dibutyl adipate (lUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (lUPAC name) (1048) + TX, diethylamide [CCN] + TX, dimethyl carbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1 137) + TX, hexamide [CCN] + TX, methoquin-butyl (1276) + TX, methylneodecanamide [CCN] + TX, oxamate [CCN] and picaridin [CCN] + TX,

an insecticide selected from the group of substances consisting of 1-dichloro-1-nitroethane (lUPAC/Chemical Abstracts name) (1058) + TX, 1 ,1-dichloro-2,2-bis(4-ethylphenyl)ethane (lUPAC name) (1056), + TX, 1 ,2-dichloropropane (lUPAC/Chemical Abstracts name) (1062) + TX, 1 ,2- dichloropropane with 1 ,3-dichloropropene (lUPAC name) (1063) + TX, 1-bromo-2-chloroethane (lUPAC/Chemical Abstracts name) (916) + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate (lUPAC name) (1451 ) + TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate (lUPAC name) (1066) + TX, 2-(1 ,3-dithiolan-2-yl)phenyl dimethylcarbamate (lUPAC/ Chemical Abstracts name) (1 109) + TX, 2-(2-butoxyethoxy)ethyl thiocyanate (lUPAC/Chemical Abstracts name) (935) + TX, 2-(4,5- dimethyl-1 ,3-dioxolan-2-yl)phenyl methylcarbamate (lUPAC/ Chemical Abstracts name) (1084) + TX, 2- (4-chloro-3,5-xylyloxy)ethanol (lUPAC name) (986) + TX, 2-chlorovinyl diethyl phosphate (lUPAC name) (984) + TX, 2-imidazolidone (lUPAC name) (1225) + TX, 2-isovalerylindan-1 ,3-dione (lUPAC name) (1246) + TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate (lUPAC name) (1284) + TX, 2- thiocyanatoethyl laurate (lUPAC name) (1433) + TX, 3-bromo-1-chloroprop-1-ene (lUPAC name) (917) + TX, 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate (lUPAC name) (1283) + TX, 4-methyl(prop-2- ynyl)amino-3,5-xylyl methylcarbamate (lUPAC name) (1285) + TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate (lUPAC name) (1085) + TX, abamectin (1 ) + TX, acephate (2) + TX, acetamiprid (4) + TX, acethion (alternative name) [CCN] + TX, acetoprole [CCN] + TX, acrinathrin (9) + TX, acrylonitrile (lUPAC name) (861 ) + TX, alanycarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, aldrin (864) + TX, allethrin (17) + TX, allosamidin (alternative name) [CCN] + TX, allyxycarb (866) + TX, alpha- cypermethrin (202) + TX, alpha-ecdysone (alternative name) [CCN] + TX, aluminium phosphide (640) + TX, amidithion (870) + TX, amidothioate (872) + TX, aminocarb (873) + TX, amiton (875) + TX, amiton hydrogen oxalate (875) + TX, amitraz (24) + TX, anabasine (877) + TX, athidathion (883) + TX, AVI 382 (compound code) + TX, AZ 60541 (compound code) + TX, azadirachtin (alternative name) (41 ) + TX, azamethiphos (42) + TX, azinphos-ethyl (44) + TX, azinphos-methyl (45) + TX, azothoate (889) + TX, Bacillus thuringiensis delta endotoxins (alternative name) (52) + TX, barium hexafluorosilicate (alternative name) [CCN] + TX, barium polysulfide (lUPAC/Chemical Abstracts name) (892) + TX, barthrin [CCN] + TX, Bayer 22/190 (development code) (893) + TX, Bayer 22408 (development code) (894) + TX, bendiocarb (58) + TX, benfuracarb (60) + TX, bensultap (66) + TX, beta-cyfluthrin (194) + TX, beta-cypermethrin (203) + TX, bifenthrin (76) + TX, bioallethrin (78) + TX, bioallethrin S- cyclopentenyl isomer (alternative name) (79) + TX, bioethanomethrin [CCN] + TX, biopermethrin (908) + TX, bioresmethrin (80) + TX, bis(2-chloroethyl) ether (lUPAC name) (909) + TX, bistrifluron (83) + TX, borax (86) + TX, brofenvalerate (alternative name) + TX, bromfenvinfos (914) + TX, bromocyclen (918) + TX, bromo-DDT (alternative name) [CCN] + TX, bromophos (920) + TX, bromophos-ethyl (921 ) + TX, bufencarb (924) + TX, buprofezin (99) + TX, butacarb (926) + TX, butathiofos (927) + TX, butocarboxim (103) + TX, butonate (932) + TX, butoxycarboxim (104) + TX, butylpyridaben (alternative name) + TX, cadusafos (109) + TX, calcium arsenate [CCN] + TX, calcium cyanide (444) + TX, calcium polysulfide (lUPAC name) (1 1 1 ) + TX, camphechlor (941 ) + TX, carbanolate (943) + TX, carbaryl (1 15) + TX, carbofuran (1 18) + TX, carbon disulfide (lUPAC/Chemical Abstracts name) (945) + TX, carbon tetrachloride (lUPAC name) (946) + TX, carbophenothion (947) + TX, carbosulfan (1 19) + TX, cartap (123) + TX, cartap hydrochloride (123) + TX, cevadine (alternative name) (725) + TX, chlorbicyclen (960) + TX, chlordane (128) + TX, chlordecone (963) + TX, chlordimeform (964) + TX, chlordimeform hydrochloride (964) + TX, chlorethoxyfos (129) + TX, chlorfenapyr (130) + TX, chlorfenvinphos (131 ) + TX, chlorfluazuron (132) + TX, chlormephos (136) + TX, chloroform [CCN] + TX, chloropicrin (141 ) + TX, chlorphoxim (989) + TX, chlorprazophos (990) + TX, chlorpyrifos (145) + TX, chlorpyrifos-methyl (146) + TX, chlorthiophos (994) + TX, chromafenozide (150) + TX, cinerin I (696) + TX, cinerin II (696) + TX, cinerins (696) + TX, cis-resmethrin (alternative name) + TX, cismethrin (80) + TX, clocythrin (alternative name) + TX, cloethocarb (999) + TX, closantel (alternative name) [CCN] + TX, clothianidin (165) + TX, copper acetoarsenite [CCN] + TX, copper arsenate [CCN] + TX, copper oleate [CCN] + TX, coumaphos (174) + TX, coumithoate (1006) + TX, crotamiton (alternative name) [CCN] + TX, crotoxyphos (1010) + TX, crufomate (101 1 ) + TX, cryolite (alternative name) (177) + TX, CS 708 (development code) (1012) + TX, cyanofenphos (1019) + TX, cyanophos (184) + TX, cyanthoate (1020) + TX, cyclethrin [CCN] + TX, cycloprothrin (188) + TX, cyfluthrin (193) + TX, cyhalothrin (196) + TX, cypermethrin (201 ) + TX, cyphenothrin (206) + TX, cyromazine (209) + TX, cythioate (alternative name) [CCN] + TX, cf-limonene (alternative name) [CCN] + TX, cf-tetramethrin (alternative name) (788) + TX, DAEP (1031 ) + TX, dazomet (216) + TX, DDT (219) + TX, decarbofuran (1034) + TX, deltamethrin (223) + TX, demephion (1037) + TX, demephion-0 (1037) + TX, demephion-S (1037) + TX, demeton (1038) + TX, demeton-methyl (224) + TX, demeton-0 (1038) + TX, demeton-O-methyl (224) + TX, demeton-S (1038) + TX, demeton-S-methyl (224) + TX, demeton-S-methylsulphon (1039) + TX, diafenthiuron (226) + TX, dialifos (1042) + TX, diamidafos (1044) + TX, diazinon (227) + TX, dicapthon (1050) + TX, dichlofenthion (1051 ) + TX, dichlorvos (236) + TX, dicliphos (alternative name) + TX, dicresyl (alternative name) [CCN] + TX, dicrotophos (243) + TX, dicyclanil (244) + TX, dieldrin (1070) + TX, diethyl 5- methylpyrazol-3-yl phosphate (lUPAC name) (1076) + TX, diflubenzuron (250) + TX, dilor (alternative name) [CCN] + TX, dimefluthrin [CCN] + TX, dimefox (1081 ) + TX, dimetan (1085) + TX, dimethoate (262) + TX, dimethrin (1083) + TX, dimethylvinphos (265) + TX, dimetilan (1086) + TX, dinex (1089) + TX, dinex-diclexine (1089) + TX, dinoprop (1093) + TX, dinosam (1094) + TX, dinoseb (1095) + TX, dinotefuran (271 ) + TX, diofenolan (1099) + TX, dioxabenzofos (1 100) + TX, dioxacarb (1 101 ) + TX, dioxathion (1 102) + TX, disulfoton (278) + TX, dithicrofos (1 108) + TX, DNOC (282) + TX, doramectin (alternative name) [CCN] + TX, DSP (1 1 15) + TX, ecdysterone (alternative name) [CCN] + TX, El 1642 (development code) (1 1 18) + TX, emamectin (291 ) + TX, emamectin benzoate (291 ) + TX, EMPC (1 120) + TX, empenthrin (292) + TX, endosulfan (294) + TX, endothion (1 121 ) + TX, endrin (1 122) + TX, EPBP (1 123) + TX, EPN (297) + TX, epofenonane (1 124) + TX, eprinomectin (alternative name) [CCN] + TX, esfenvalerate (302) + TX, etaphos (alternative name) [CCN] + TX, ethiofencarb (308) + TX, ethion (309) + TX, ethiprole (310) + TX, ethoate-m ethyl (1 134) + TX, ethoprophos (312) + TX, ethyl formate (lUPAC name) [CCN] + TX, ethyl-DDD (alternative name) (1056) + TX, ethylene dibromide (316) + TX, ethylene dichloride (chemical name) (1 136) + TX, ethylene oxide [CCN] + TX, etofenprox (319) + TX, etrimfos (1 142) + TX, EXD (1 143) + TX, famphur (323) + TX, fenamiphos (326) + TX, fenazaflor (1 147) + TX, fenchlorphos (1 148) + TX, fenethacarb (1 149) + TX, fenfluthrin (1 150) + TX, fenitrothion (335) + TX, fenobucarb (336) + TX, fenoxacrim (1 153) + TX, fenoxycarb (340) + TX, fenpirithrin (1 155) + TX, fenpropathrin (342) + TX, fenpyrad (alternative name) + TX, fensulfothion (1 158) + TX, fenthion (346) + TX, fenthion-ethyl [CCN] + TX, fenvalerate (349) + TX, fipronil (354) + TX, flonicamid (358) + TX, flubendiamide (CAS. Reg. No.: 272451-65-7) + TX, flucofuron (1 168) + TX, flucycloxuron (366) + TX, flucythrinate (367) + TX, fluenetil (1 169) + TX, flufenerim [CCN] + TX, flufenoxuron (370) + TX, flufenprox (1 171 ) + TX, flumethrin (372) + TX, fluvalinate (1 184) + TX, FMC 1 137 (development code) (1 185) + TX, fonofos (1 191 ) + TX, formetanate (405) + TX, formetanate hydrochloride (405) + TX, formothion (1 192) + TX, formparanate (1 193) + TX, fosmethilan (1 194) + TX, fospirate (1 195) + TX, fosthiazate (408) + TX, fosthietan (1 196) + TX, furathiocarb (412) + TX, furethrin (1200) + TX, gamma-cyhalothrin (197) + TX, gamma-HCH (430) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, GY-81 (development code) (423) + TX, halfenprox (424) + TX, halofenozide (425) + TX, HCH (430) + TX, HEOD (1070) + TX, heptachlor (121 1 ) + TX, heptenophos (432) + TX, heterophos [CCN] + TX, hexaflumuron (439) + TX, HHDN (864) + TX, hydramethylnon (443) + TX, hydrogen cyanide (444) + TX, hydroprene (445) + TX, hyquincarb (1223) + TX, imidacloprid (458) + TX, imiprothrin (460) + TX, indoxacarb (465) + TX, iodomethane (lUPAC name) (542) + TX, IPSP (1229) + TX, isazofos (1231 ) + TX, isobenzan (1232) + TX, isocarbophos (alternative name) (473) + TX, isodrin (1235) + TX, isofenphos (1236) + TX, isolane (1237) + TX, isoprocarb (472) + TX, isopropyl 0-(methoxy- aminothiophosphoryl)salicylate (lUPAC name) (473) + TX, isoprothiolane (474) + TX, isothioate (1244) + TX, isoxathion (480) + TX, ivermectin (alternative name) [CCN] + TX, jasmolin I (696) + TX, jasmolin II (696) + TX, jodfenphos (1248) + TX, juvenile hormone I (alternative name) [CCN] + TX, juvenile hormone II (alternative name) [CCN] + TX, juvenile hormone III (alternative name) [CCN] + TX, kelevan (1249) + TX, kinoprene (484) + TX, lambda-cyhalothrin (198) + TX, lead arsenate [CCN] + TX, lepimectin (CCN) + TX, leptophos (1250) + TX, lindane (430) + TX, lirimfos (1251 ) + TX, lufenuron (490) + TX, lythidathion (1253) + TX, m-cumenyl methylcarbamate (lUPAC name) (1014) + TX, magnesium phosphide (lUPAC name) (640) + TX, malathion (492) + TX, malonoben (1254) + TX, mazidox (1255) + TX, mecarbam (502) + TX, mecarphon (1258) + TX, menazon (1260) + TX, mephosfolan (1261 ) + TX, mercurous chloride (513) + TX, mesulfenfos (1263) + TX, metaflumizone (CCN) + TX, metam (519) + TX, metam-potassium (alternative name) (519) + TX, metam-sodium (519) + TX, methacrifos (1266) + TX, methamidophos (527) + TX, methanesulfonyl fluoride (lUPAC/Chemical Abstracts name) (1268) + TX, methidathion (529) + TX, methiocarb (530) + TX, methocrotophos (1273) + TX, methomyl (531 ) + TX, methoprene (532) + TX, methoquin-butyl (1276) + TX, methothrin (alternative name) (533) + TX, methoxychlor (534) + TX, methoxyfenozide (535) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, methylchloroform (alternative name) [CCN] + TX, methylene chloride [CCN] + TX, metofluthrin [CCN] + TX, metolcarb (550) + TX, metoxadiazone (1288) + TX, mevinphos (556) + TX, mexacarbate (1290) + TX, milbemectin (557) + TX, milbemycin oxime (alternative name) [CCN] + TX, mipafox (1293) + TX, mirex (1294) + TX, monocrotophos (561 ) + TX, morphothion (1300) + TX, moxidectin (alternative name) [CCN] + TX, naftalofos (alternative name) [CCN] + TX, naled (567) + TX, naphthalene (lUPAC/Chemical Abstracts name) (1303) + TX, NC-170 (development code) (1306) + TX, NC-184 (compound code) + TX, nicotine (578) + TX, nicotine sulfate (578) + TX, nifluridide (1309) + TX, nitenpyram (579) + TX, nithiazine (131 1 ) + TX, nitrilacarb (1313) + TX, nitrilacarb 1 :1 zinc chloride complex (1313) + TX, NNI-0101 (compound code) + TX, NNI-0250 (compound code) + TX, nornicotine (traditional name) (1319) + TX, novaluron (585) + TX, noviflumuron (586) + TX, 0-5-dichloro-4- iodophenyl O-ethyl ethylphosphonothioate (lUPAC name) (1057) + TX, 0,0-diethyl 0-4-methyl-2-oxo- 2A -chromen-7-yl phosphorothioate (lUPAC name) (1074) + TX, Ο,Ο-diethyl 0-6-methyl-2- propylpyrimidin-4-yl phosphorothioate (lUPAC name) (1075) + TX, 0,0, 0',Ο'-tetrapropyl dithiopyrophosphate (lUPAC name) (1424) + TX, oleic acid (lUPAC name) (593) + TX, omethoate (594) + TX, oxamyl (602) + TX, oxydemeton-methyl (609) + TX, oxydeprofos (1324) + TX, oxydisulfoton (1325) + TX, pp'-DDT (219) + TX, para-dichlorobenzene [CCN] + TX, parathion (615) + TX, parathion-methyl (616) + TX, penfluron (alternative name) [CCN] + TX, pentachlorophenol (623) + TX, pentachlorophenyl laurate (lUPAC name) (623) + TX, permethrin (626) + TX, petroleum oils (alternative name) (628) + TX, PH 60-38 (development code) (1328) + TX, phenkapton (1330) + TX, phenothrin (630) + TX, phenthoate (631 ) + TX, phorate (636) + TX, phosalone (637) + TX, phosfolan (1338) + TX, phosmet (638) + TX, phosnichlor (1339) + TX, phosphamidon (639) + TX, phosphine (lUPAC name) (640) + TX, phoxim (642) + TX, phoxim-methyl (1340) + TX, pirimetaphos (1344) + TX, pirimicarb (651 ) + TX, pirimiphos-ethyl (1345) + TX, pirimiphos-methyl (652) + TX, polychlorodicyclopentadiene isomers (lUPAC name) (1346) + TX, polychloroterpenes (traditional name) (1347) + TX, potassium arsenite [CCN] + TX, potassium thiocyanate [CCN] + TX, prallethrin (655) + TX, precocene I (alternative name) [CCN] + TX, precocene II (alternative name) [CCN] + TX, precocene III (alternative name) [CCN] + TX, primidophos (1349) + TX, profenofos (662) + TX, profluthrin [CCN] + TX, promacyl (1354) + TX, promecarb (1355) + TX, propaphos (1356) + TX, propetamphos (673) + TX, propoxur (678) + TX, prothidathion (1360) + TX, prothiofos (686) + TX, prothoate (1362) + TX, protrifenbute [CCN] + TX, pymetrozine (688) + TX, pyraclofos (689) + TX, pyrazophos (693) + TX, pyresmethrin (1367) + TX, pyrethrin I (696) + TX, pyrethrin II (696) + TX, pyrethrins (696) + TX, pyridaben (699) + TX, pyridalyl (700) + TX, pyridaphenthion (701 ) + TX, pyrimidifen (706) + TX, pyrimitate (1370) + TX, pyriproxyfen (708) + TX, quassia (alternative name) [CCN] + TX, quinalphos (71 1 ) + TX, quinalphos-methyl (1376) + TX, quinothion (1380) + TX, quintiofos (1381 ) + TX, R-1492 (development code) (1382) + TX, rafoxanide (alternative name) [CCN] + TX, resmethrin (719) + TX, rotenone (722) + TX, RU 15525 (development code) (723) + TX, RU 25475 (development code) (1386) + TX, ryania (alternative name) (1387) + TX, ryanodine (traditional name) (1387) + TX, sabadilla (alternative name) (725) + TX, schradan (1389) + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, SI-0009 (compound code) + TX, SI-0205 (compound code) + TX, SI-0404 (compound code) + TX, SI-0405 (compound code) + TX, silafluofen (728) + TX, SN 72129 (development code) (1397) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoride (lUPAC/Chemical Abstracts name) (1399) + TX, sodium hexafluorosilicate (1400) + TX, sodium pentachlorophenoxide (623) + TX, sodium selenate (lUPAC name) (1401 ) + TX, sodium thiocyanate [CCN] + TX, sophamide (1402) + TX, spinosad (737) + TX, spiromesifen (739) + TX, spirotetrmat (CCN) + TX, sulcofuron (746) + TX, sulcofuron-sodium (746) + TX, sulfluramid (750) + TX, sulfotep (753) + TX, sulfuryl fluoride (756) + TX, sulprofos (1408) + TX, tar oils (alternative name) (758) + TX, tau-fluvalinate (398) + TX, tazimcarb (1412) + TX, TDE (1414) + TX, tebufenozide (762) + TX, tebufenpyrad (763) + TX, tebupirimfos (764) + TX, teflubenzuron (768) + TX, tefluthrin (769) + TX, temephos (770) + TX, TEPP (1417) + TX, terallethrin (1418) + TX, terbam (alternative name) + TX, terbufos (773) + TX, tetrachloroethane [CCN] + TX, tetrachlorvinphos (777) + TX, tetramethrin (787) + TX, theta-cypermethrin (204) + TX, thiacloprid (791 ) + TX, thiafenox (alternative name) + TX, thiamethoxam (792) + TX, thicrofos (1428) + TX, thiocarboxime (1431 ) + TX, thiocyclam (798) + TX, thiocyclam hydrogen oxalate (798) + TX, thiodicarb (799) + TX, thiofanox (800) + TX, thiometon (801 ) + TX, thionazin (1434) + TX, thiosultap (803) + TX, thiosultap-sodium (803) + TX, thuringiensin (alternative name) [CCN] + TX, tolfenpyrad (809) + TX, tralomethrin (812) + TX, transfluthrin (813) + TX, transpermethrin (1440) + TX, triamiphos (1441 ) + TX, triazamate (818) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, trichlorfon (824) + TX, trichlormetaphos-3 (alternative name) [CCN] + TX, trichloronat (1452) + TX, trifenofos (1455) + TX, triflumuron (835) + TX, trimethacarb (840) + TX, triprene (1459) + TX, vamidothion (847) + TX, vaniliprole [CCN] + TX, veratridine (alternative name) (725) + TX, veratrine (alternative name) (725) + TX, XMC (853) + TX, xylylcarb (854) + TX, YI-5302 (compound code) + TX, zeta-cypermethrin (205) + TX, zetamethrin (alternative name) + TX, zinc phosphide (640) + TX, zolaprofos (1469) and ZXI 8901 (development code) (858) + TX, cyantraniliprole [736994-63-19 + TX, chlorantraniliprole [500008-45-7] + TX, cyenopyrafen [560121-52-0] + TX, cyflumetofen [400882-07-7] + TX, pyrifluquinazon [337458-27-2] + TX, spinetoram [187166-40-1 + 187166-15-0] + TX, spirotetramat [203313-25-1] + TX, sulfoxaflor [946578-00-3] + TX, flufiprole [704886-18-0] + TX, meperfluthrin [915288-13-0] + TX, tetramethylfluthrin [84937-88-2] + TX, triflumezopyrim (disclosed in WO 2012/0921 15) + TX,

a molluscicide selected from the group of substances consisting of bis(tributyltin) oxide (lUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, cloethocarb (999) + TX, copper acetoarsenite [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, ferric phosphate (lUPAC name) (352) + TX, metaldehyde (518) + TX, methiocarb (530) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX, pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, tazimcarb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913) + TX, trifenmorph (1454) + TX, trimethacarb (840) + TX, triphenyltin acetate (lUPAC name) (347) and triphenyltin hydroxide (lUPAC name) (347) + TX, pyriprole [394730-71-3] + TX,

a nematicide selected from the group of substances consisting of AKD-3088 (compound code) + TX, 1 ,2-dibromo-3-chloropropane (lUPAC/Chemical Abstracts name) (1045) + TX, 1 ,2- dichloropropane (lUPAC/ Chemical Abstracts name) (1062) + TX, 1 ,2-dichloropropane with 1 ,3- dichloropropene (lUPAC name) (1063) + TX, 1 ,3-dichloropropene (233) + TX, 3,4- dichlorotetrahydrothiophene 1 , 1-dioxide (lUPAC/Chemical Abstracts name) (1065) + TX, 3-(4- chlorophenyl)-5-methylrhodanine (lUPAC name) (980) + TX, 5-methyl-6-thioxo-1 ,3,5-thiadiazinan-3- ylacetic acid (lUPAC name) (1286) + TX, 6-isopentenylaminopurine (alternative name) (210) + TX, abamectin (1 ) + TX, acetoprole [CCN] + TX, alanycarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, AZ 60541 (compound code) + TX, benclothiaz [CCN] + TX, benomyl (62) + TX, butylpyridaben (alternative name) + TX, cadusafos (109) + TX, carbofuran (1 18) + TX, carbon disulfide (945) + TX, carbosulfan (1 19) + TX, chloropicrin (141 ) + TX, chlorpyrifos (145) + TX, cloethocarb (999) + TX, cytokinins (alternative name) (210) + TX, dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamidafos (1044) + TX, dichlofenthion (1051 ) + TX, dicliphos (alternative name) + TX, dimethoate (262) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291 ) + TX, emamectin benzoate (291 ) + TX, eprinomectin (alternative name) [CCN] + TX, ethoprophos (312) + TX, ethylene dibromide (316) + TX, fenamiphos (326) + TX, fenpyrad (alternative name) + TX, fensulfothion (1 158) + TX, fosthiazate (408) + TX, fosthietan (1 196) + TX, furfural (alternative name) [CCN] + TX, GY-81 (development code) (423) + TX, heterophos [CCN] + TX, iodomethane (lUPAC name) (542) + TX, isamidofos (1230) + TX, isazofos (1231 ) + TX, ivermectin (alternative name) [CCN] + TX, kinetin (alternative name) (210) + TX, mecarphon (1258) + TX, metam (519) + TX, metam-potassium (alternative name) (519) + TX, metam- sodium (519) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, Myrothecium verrucaria composition (alternative name) (565) + TX, NC-184 (compound code) + TX, oxamyl (602) + TX, phorate (636) + TX, phosphamidon (639) + TX, phosphocarb [CCN] + TX, sebufos (alternative name) + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) + TX, terbam (alternative name) + TX, terbufos (773) + TX, tetrachlorothiophene (lUPAC/ Chemical Abstracts name) (1422) + TX, thiafenox (alternative name) + TX, thionazin (1434) + TX, triazophos (820) + TX, triazuron (alternative name) + TX, xylenols [CCN] + TX, YI-5302 (compound code) and zeatin (alternative name) (210) + TX, fluensulfone [318290-98-1] + TX,

a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580) + TX,

a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Reynoutria sachalinensis extract (alternative name) (720) + TX,

a rodenticide selected from the group of substances consisting of 2-isovalerylindan-1 ,3-dione

(lUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (lUPAC name) (748) + TX, alpha-chlorohydrin [CCN] + TX, aluminium phosphide (640) + TX, antu (880) + TX, arsenous oxide (882) + TX, barium carbonate (891 ) + TX, bisthiosemi (912) + TX, brodifacoum (89) + TX, bromadiolone (91 ) + TX, bromethalin (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorophacinone (140) + TX, cholecalciferol (alternative name) (850) + TX, coumachlor (1004) + TX, coumafuryl (1005) + TX, coumatetralyl (175) + TX, crimidine (1009) + TX, difenacoum (246) + TX, difethialone (249) + TX, diphacinone (273) + TX, ergocalciferol (301 ) + TX, flocoumafen (357) + TX, fluoroacetamide (379) + TX, flupropadine (1 183) + TX, flupropadine hydrochloride (1183) + TX, gamma-HCH (430) + TX, HCH (430) + TX, hydrogen cyanide (444) + TX, iodomethane (lUPAC name) (542) + TX, lindane (430) + TX, magnesium phosphide (lUPAC name) (640) + TX, methyl bromide (537) + TX, norbormide (1318) + TX, phosacetim (1336) + TX, phosphine (lUPAC name) (640) + TX, phosphorus [CCN] + TX, pindone (1341 ) + TX, potassium arsenite [CCN] + TX, pyrinuron (1371 ) + TX, scilliroside (1390) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoroacetate (735) + TX, strychnine (745) + TX, thallium sulfate [CCN] + TX, warfarin (851 ) and zinc phosphide (640) + TX,

a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl piperonylate (lUPAC name) (934) + TX, 5-(1 ,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (lUPAC name) (903) + TX, farnesol with nerolidol (alternative name) (324) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code) (296) + TX, piperonyl butoxide (649) + TX, piprotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesasmolin (1394) and sulfoxide (1406) + TX,

5 an animal repellent selected from the group of substances consisting of anthraquinone (32) +

TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171 ) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, methiocarb (530) + TX, pyridin-4-amine (lUPAC name) (23) + TX, thiram (804) + TX, trimethacarb (840) + TX, zinc naphthenate [CCN] and ziram (856) + TX,

10 a virucide selected from the group of substances consisting of imanin (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX,

a wound protectant selected from the group of substances consisting of mercuric oxide (512) + TX, octhilinone (590) and thiophanate-methyl (802) + TX,

and biologically active compounds selected from the group consisting of ametoctradin [865318-

15 97-4] + TX, amisulbrom [348635-87-0] + TX, azaconazole [60207-31-0] + TX, benzovindiflupyr

[1072957-71-1] + TX, bitertanol [70585-36-3] + TX, bixafen [581809-46-3] + TX, bromuconazole [1 16255-48-2] + TX, coumoxystrobin [850881-70-8] + TX, cyproconazole [94361-06-5] + TX, difenoconazole [1 19446-68-3] + TX, diniconazole [83657-24-3] + TX, enoxastrobin [238410-1 1-2] + TX, epoxiconazole [106325-08-0] + TX, fenbuconazole [1 14369-43-6] + TX, fenpyrazamine [473798-59-3]

20 + TX, fluquinconazole [136426-54-5] + TX, flusilazole [85509-19-9] + TX, flutriafol [76674-21-0] + TX, fluxapyroxad [907204-31-3] + TX, fluopyram [658066-35-4] + TX, fenaminstrobin [366815-39-6] + TX, isofetamid [875915-78-9] + TX, hexaconazole [79983-71-4] + TX, imazalil [35554-44-0] + TX, imiben- conazole [86598-92-7] + TX, ipconazole [125225-28-7] + TX, ipfentrifluconazole [1417782-08-1 ] + TX, isotianil [224049-04-1] + TX, mandestrobin [173662-97-0] (can be prepared according to the procedures

25 described in WO 2010/093059) + TX, mefentrifluconazole [1417782-03-6] + TX, metconazole [1251 16- 23-6] + TX, myclobutanil [88671-89-0] + TX, paclobutrazol [76738-62-0] + TX, pefurazoate [101903-30- 4] + TX, penflufen [494793-67-8] + TX, penconazole [66246-88-6] + TX, prothioconazole [178928-70-6] + TX, pyrifenox [88283-41-4] + TX, prochloraz [67747-09-5] + TX, propiconazole [60207-90-1] + TX, simeconazole [149508-90-7] + TX, tebuconazole [107534-96-3] + TX, tetraconazole [1 12281-77-3] +

30 TX, triadimefon [43121-43-3] + TX, triadimenol [55219-65-3] + TX, triflumizole [99387-89-0] + TX, triticonazole [131983-72-7] + TX, ancymidol [12771-68-5] + TX, fenarimol [60168-88-9] + TX, nuarimol [63284-71-9] + TX, bupirimate [41483-43-6] + TX, dimethirimol [5221-53-4] + TX, ethirimol [23947-60- 6] + TX, dodemorph [1593-77-7] + TX, fenpropidin [67306-00-7] + TX, fenpropimorph [67564-91-4] + TX, spiroxamine [1 18134-30-8] + TX, tridemorph [81412-43-3] + TX, cyprodinil [121552-61-2] + TX,

35 mepanipyrim [1 10235-47-7] + TX, pyrimethanil [531 12-28-0] + TX, fenpiclonil [74738-17-3] + TX, fludioxonil [131341-86-1] + TX, fluindapyr [1383809-87-7] + TX, benalaxyl [71626-1 1-4] + TX, furalaxyl [57646-30-7] + TX, metalaxyl [57837-19-1 ] + TX, R-metalaxyl [70630-17-0] + TX, ofurace [58810-48-3] + TX, oxadixyl [77732-09-3] + TX, benomyl [17804-35-2] + TX, carbendazim [10605-21-7] + TX, debacarb [62732-91-6] + TX, fuberidazole [3878-19-1] + TX, thiabendazole [148-79-8] + TX,

40 chlozolinate [84332-86-5] + TX, dichlozoline [24201-58-9] + TX, iprodione [36734-19-7] + TX, myclozoline [54864-61-8] + TX, procymidone [32809-16-8] + TX, vinclozoline [50471-44-8] + TX, boscalid [188425-85-6] + TX, carboxin [5234-68-4] + TX, fenfuram [24691-80-3] + TX, flutolanil [66332- 96-5] + TX, flutianil [958647-10-4] + TX, mepronil [55814-41-0] + TX, oxycarboxin [5259-88-1] + TX, penthiopyrad [183675-82-3] + TX, thifluzamide [130000-40-7] + TX, guazatine [108173-90-6] + TX, dodine [2439-10-3] [1 12-65-2] (free base) + TX, iminoctadine [13516-27-3] + TX, azoxystrobin [131860- 5 33-8] + TX, dimoxystrobin [149961-52-4] + TX, enestroburin {Proc. BCPC, Int. Congr., Glasgow, 2003,

1 , 93} + TX, fluoxastrobin [361377-29-9] + TX, kresoxim-methyl [143390-89-0] + TX, metominostrobin [133408-50-1] + TX, trifloxystrobin [141517-21-7] + TX, orysastrobin [248593-16-0] + TX, picoxystrobin [1 17428-22-5] + TX, pyraclostrobin [175013-18-0] + TX, pyraoxystrobin [862588-1 1-2] + TX, ferbam [14484-64-1] + TX, mancozeb [8018-01-7] + TX, maneb [12427-38-2] + TX, metiram [9006-42-2] + TX, 10 propineb [12071-83-9] + TX, thiram [137-26-8] + TX, zineb [12122-67-7] + TX, ziram [137-30-4] + TX, captafol [2425-06-1] + TX, captan [133-06-2] + TX, dichlofluanid [1085-98-9] + TX, fluoroimide [41205-

21- 4] + TX, folpet [133-07-3 ] + TX, tolylfluanid [731-27-1] + TX, bordeaux mixture [801 1-63-0] + TX, copperhydroxid [20427-59-2] + TX, copperoxychlorid [1332-40-7] + TX, coppersulfat [7758-98-7] + TX, copperoxid [1317-39-1] + TX, mancopper [53988-93-5] + TX, oxine-copper [10380-28-6] + TX, dinocap

15 [131-72-6] + TX, nitrothal-isopropyl [10552-74-6] + TX, edifenphos [17109-49-8] + TX, iprobenphos

[26087-47-8] + TX, isoprothiolane [50512-35-1] + TX, phosdiphen [36519-00-3] + TX, pyrazophos [13457-18-6] + TX, tolclofos-m ethyl [57018-04-9] + TX, acibenzolar-S-methyl [135158-54-2] + TX, anilazine [101-05-3] + TX, benthiavalicarb [413615-35-7] + TX, blasticidin-S [2079-00-7] + TX, chinomethionat [2439-01-2] + TX, chloroneb [2675-77-6] + TX, chlorothalonil [1897-45-6] + TX,

20 cyflufenamid [180409-60-3] + TX, cymoxanil [57966-95-7] + TX, dichlone [1 17-80-6] + TX, diclocymet

[139920-32-4] + TX, diclomezine [62865-36-5] + TX, dicloran [99-30-9] + TX, diethofencarb [87130-20- 9] + TX, dimethomorph [1 10488-70-5] + TX, SYP-LI90 (Flumorph) [21 1867-47-9] + TX, dithianon [3347-

22- 6] + TX, ethaboxam [162650-77-3] + TX, etridiazole [2593-15-9] + TX, famoxadone [131807-57-3] + TX, fenamidone [161326-34-7] + TX, fenoxanil [1 15852-48-7] + TX, fentin [668-34-8] + TX, ferimzone

25 [89269-64-7] + TX, fluazinam [79622-59-6] + TX, fluopicolide [2391 10-15-7] + TX, flusulfamide [106917- 52-6] + TX, fenhexamid [126833-17-8] + TX, fosetyl-aluminium [39148-24-8] + TX, hymexazol [10004- 44-1] + TX, iprovalicarb [140923-17-7] + TX, IKF-916 (Cyazofamid) [1201 16-88-3] + TX, kasugamycin [6980-18-3] + TX, methasulfocarb [66952-49-6] + TX, metrafenone [220899-03-6] + TX, pencycuron [66063-05-6] + TX, phthalide [27355-22-2] + TX, picarbutrazox [500207-04-5] + TX, polyoxins [1 1 1 13-

30 80-7] + TX, probenazole [27605-76-1] + TX, propamocarb [25606-41-1] + TX, proquinazid [189278-12- 4] + TX, pydiflumetofen [1228284-64-7] + TX, pyrametostrobin [915410-70-7] + TX, pyroquilon [57369- 32-1] + TX, pyriofenone [688046-61-9] + TX, pyribencarb [799247-52-2] + TX, pyrisoxazole [847749- 37-5] + TX, quinoxyfen [124495-18-7] + TX, quintozene [82-68-8] + TX, sulfur [7704-34-9] + TX, Timorex Gold™ (plant extract containing tea tree oil from the Stockton Group) + TX, tebufloquin [376645-78-2] +

35 TX, tiadinil [223580-51-6] + TX, triazoxide [72459-58-6] + TX, tolprocarb [91 1499-62-2] + TX, triclopyricarb [902760-40-1] + TX, tricyclazole [41814-78-2] + TX, triforine [26644-46-2] + TX, validamycin [37248-47-8] + TX, valifenalate [283159-90-0] + TX, zoxamide (RH7281 ) [156052-68-5] + TX, mandipropamid [374726-62-2] + TX, isopyrazam [881685-58-1] + TX, phenamacril + TX, sedaxane [874967-67-6] + TX, trinexapac-ethyl [95266-40-3] + TX, 3-difluoromethyl-1-methyl-1 H-pyrazole-4-

40 carboxylic acid (9-dichloromethylene-1 ,2,3,4-tetrahydro-1 ,4-methano-naphthalen-5-yl)-amide (dislosed in WO 2007/048556) + TX, 3-difluoromethyl-1-methyl-1 H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro- biphenyl-2-yl)-amide (disclosed in WO 2006/087343) + TX, [(3S,4R,4aR,6S,6aS, 12R, 12aS, 12bS)-3- [(cyclopropylcarbonyl)oxy]- 1 ,3,4,4a,5,6,6a, 12, 12a, 12b-decahydro-6, 12-dihydroxy-4,6a,12b-trimethyl- 1 1-oxo-9-(3-pyridinyl)-2H, 1 1 /-/naphtho[2, 1 ]pyrano[3,4-e]pyran-4-yl]methyl-cyclopropanecarboxylate [915972-17-7] + TX and 1 ,3,5-trimethyl-N-(2-methyl-1-oxopropyl)-N-[3-(2-methylpropyl )-4-[2,2,2- 5 trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]phenyl]-1 H-pyrazole-4-carboxamide [926914-55-8] + TX, or a biologically active compound selected from the group consisting of N-[(5-chloro-2-isopropyl- phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-m ethyl-pyrazole-4-carboxamide (can be prepared according to the procedures described in WO 2010/130767) + TX, 2,6-Dimethyl-1 H,5H- [1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetrone (can be prepared according to the procedures

10 described in WO 201 1/138281 ) + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1 ,4]dithiino[1 ,2-c]isothiazole-3- carbonitrile + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5 -dimethyl-pyrazol-3- amine (can be prepared according to the procedures described in WO 2012/031061 ) + TX, 3- (difluoromethyl)-N-(7-fluoro-1 , 1 ,3-trimethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide (can be prepared according to the procedures described in WO 2012/084812) + TX, CAS 850881-30-0 + TX, 3-

15 (3,4-dichloro-1 ,2-thiazol-5-ylmethoxy)-1 ,2-benzothiazole 1 , 1-dioxide (can be prepared according to the procedures described in WO 2007/129454) + TX, 2-[2-[(2,5-dimethylphenoxy)methyl]phenyl]-2- methoxy-N-methyl-acetamide + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)qui nolone (can be prepared according to the procedures described in WO 2005/070917) + TX, 2-[2-fluoro-6-[(8- fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol (can be prepared according to the procedures

20 described in WO 201 1/081 174) + TX, 2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro- phenyl]propan-2-ol (can be prepared according to the procedures described in WO 201 1/081 174) + TX, oxathiapiprolin + TX [1003318-67-9], tert-butyl N-[6-[[[(1-methyltetrazol-5-yl)-phenyl- methylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, N-[2-(3,4-difluorophenyl)phenyl]-3- (trifluoromethyl)pyrazine-2-carboxamide (can be prepared according to the procedures described in WO

25 2007/ 072999) + TX, 3-(difluoromethyl)-1-methyl-N-[(3R)-1 , 1 ,3-trimethylindan-4-yl]pyrazole-4- carboxamide (can be prepared according to the procedures described in WO 2014/013842) + TX, 2,2,2- trifluoroethyl N-[2-methyl-1-[[(4-methylbenzoyl)amino]methyl]propyl]carbama te + TX, (2RS)-2-[4-(4- chlorophenoxy)-a,a,a-trifluoro-o-tolyl]-1-(1 H-1 ,2,4-triazol-1-yl)propan-2-ol + TX, (2RS)-2-[4-(4- chlorophenoxy)-a,a,a-trifluoro-o-tolyl]-3-methyl-1-(1 H-1 ,2,4-triazol-1-yl)butan-2-ol + TX, 2-

30 (difluoromethyl)-N-[(3R)-3-ethyl-1 , 1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, 2- (difluoromethyl)-N-[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 (can be prepared according to the procedures described in WO 2007/031513) + TX, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]- 4-piperidyl]thiazol-4-yl]-

35 4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl] methanesulfonate (can be prepared according to the procedures described in WO 2012/025557) + TX, but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl- methylene]amino]oxymethyl]-2-pyridyl]carbamate (can be prepared according to the procedures described in WO 2010/000841 ) + TX, 2-[[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]met hyl]- 4H-1 ,2,4-triazole-3-thione (can be prepared according to the procedures described in WO 2010/146031 )

40 + TX, methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]m ethyl]carbamate + TX, 3- chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine (can be prepared according to the procedures described in WO 2005/121 104) + TX, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1 -(1 ,2,4- triazol-1 -yl)propan-2-ol (can be prepared according to the procedures described in WO 2013/024082) + TX, 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine (can be prepared according to the procedures described in WO 2012/020774) + TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine- 3-carbonitrile (can be prepared according to the procedures described in WO 2012/020774) + TX, (R)- 3-(difluoromethyl)-1 -methyl-N-[1 , 1 ,3-trimethylindan-4-yl]pyrazole-4-carboxamide (can be prepared according to the procedures described in WO 201 1/162397 ) + TX, 3-(difluoromethyl)-N-(7-fluoro-1 , 1 ,3- trimethyl-indan-4-yl)-1 -methyl-pyrazole-4-carboxamide (can be prepared according to the procedures described in WO 2012/084812) + TX, 1 -[2-[[1 -(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl- phenyl]-4-methyl-tetrazol-5-one (can be prepared according to the procedures described in WO 2013/162072) + TX, 1 -methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1 - yl)phenoxy]methyl]phenyl]tetrazol-5-one (can be prepared according to the procedures described in WO 2014/051 165) + TX, (Z,2E)-5-[1 -(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethy l- pent-3-enamide + TX, (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate + TX, N-(5- chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5 -fluoro-1 -methylpyrazole-4-carboxamide [1255734-28-1 ] (can be prepared according to the procedures described in WO 2010/130767) + TX, 3- (difluoromethyl)-N-[(R)-2,3-dihydro-1 , 1 ,3-trimethyl-1 H-inden-4-yl]-1 -methylpyrazole-4-carboxami^ [1352994-67-2] + TX, N^2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidin e + TX, N'-[4- (4,5-dichloro-thiazol-2-yloxy)-2,5-dimethyl-phenyl]-N-ethyl- N-methyl-formamidine + TX, N'-(2,5- dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-fornrianriidine + TX, N'-[4-(4,5-dichloro-thiazol-2-yloxy)- 2 5-dimethyl-phenyl]-N-ethyl-N-methyl-fornrianriidine + TX,

O (fenpicoxamid [517875-34-2]) + TX (as described in WO

2003/035617), aminopyrifen [1531626-08-0] + TX, florylpicoxamid [1961312-55-9] (as described in WO 2016/109257) + TX, inpyrfluxam [1352994-67-2] + TX, ipflufenoquin [1314008-27-9] + TX, isoflucypram [1255734-28-1 ] +TX, pyrapropoyne [1803108-03-3] + TX, pyraziflumid [942515-63-1 ] +TX, pyridachlometyl [1358061 -55-8] +TX, quinofumelin [861647-84-9] + TX, 4-[[6-[2-(2,4- difluorophenyl)-1 , 1 -difluoro-2-hydroxy-3-(1 ,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile (can be prepared according to the procedures described in WO 2016/187201 ) + TX, 2-(difluoromethyl)-N- (1 , 1 ,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-(3-ethyl-1 , 1 -dimethyl- indan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-(1 , 1 -dimethyl-3-propyl-indan-4- yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-(3-isobutyl-1 , 1 -dimethyl-indan-4-yl)pyridine-3- carboxamide + TX, 2-(difluoromethyl)-N-[(3R)-1 , 1 ,3-trimethylindan-4-yl]pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1 , 1 -dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, and 2- (difluoromethyl)-N-[(3R)-1 , 1 -dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide + TX, wherein each of these carboxamide compounds can be prepared according to the procedures described in WO 2014/095675 and/or WO 2016/139189.

The references in brackets behind the active ingredients, e.g. [3878-19-1] refer to the Chemical Abstracts Registry number. The above described mixing partners are known. Where the active ingredients are included in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: C. D. S. TomLin; The British Crop Protection Council], they are described therein under the entry number given in round brackets hereinabove for the particular compound; for example, the compound "abamectin" is described under entry number (1 ). Where "[CCN]" is added hereinabove to the particular compound, the compound in question is included in the "Compendium of Pesticide Common Names", which is accessible on the internet [A. Wood; Compendium of Pesticide Common Names, Copyright © 1995-2004]; for example, the compound "acetoprole" is described under the internet address http://www.alanwood.net/pesticides/acetoprole.html.

Most of the active ingredients described above are referred to hereinabove by 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 "develoment 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 described in Tables 1.1 to 1.19 (below) or Table A (compounds A-1 to A-63) (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 a compound described in Tables 1.1 to 1.19 (below) or Table A (compounds A-1 to A-63) (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 described in Tables 1.1 to 1.19 (below) or Table A (compounds A-1 to A-63) (below), and the active ingredient(s) as described above, is not essential for working the present invention.

The compositions according to the invention can also comprise further solid or liquid auxiliaries, such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematocides, plant activators, molluscicides or herbicides.

The compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and/or compressing a solid active ingredient and in the presence of at least one auxiliary for example by intimately mixing and/or grinding the active ingredient with the auxiliary (auxiliaries). These processes for the preparation of the compositions and the use of the compounds of formula (I) for the preparation of these compositions are also a subject of the invention. Another aspect of the invention is related to the use of a compound of formula (I) or of a preferred individual compound as defined herein, 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 the 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 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 1g 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.

Suitably, a composition comprising a compound of formula (I) according to the present invention is applied either preventative, meaning prior to disease development or curative, meaning after disease development.

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 ondensation 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) optionally together with 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.

Whereas it is preferred to formulate commercial products as concentrates, the end user will normally use dilute formulations.

The compounds in Tables 1.1 to 1.19 below illustrate the compounds of the invention. The skilled person would understand that the compounds of formula (I) may exist as E and/or Z isomers as described hereinbefore. Where mentioned the specific geometric configuration is not considered to be limiting.

Each of Tables 1.2 to 1.19 (which follow Table 1.1 ) discloses 165 individual compounds of the formula (I) in which R ² and R ³ is specifically defined in Tables 1.2 to 1.19, which refer to Table Z.1 wherein R , R ⁴ , R ⁵ and R ⁶ are specifically defined.

Table Z.1

Compound R ¹ R ⁴ R ⁵ R ⁶

El.l H CH ₃ cyclopropyl CH ₃

El.2 H CH ₃ H ₂ C=CH- CH ₃

E1.3 H CH ₃ (CH ₃ ) ₂ C=CH- CH ₃ Compound R ¹ R ⁴ R ⁵ R ⁶

E1.4 H CH ₃ (CH ₃ CH ₂ ) ₂ C=CH- CH ₃

E1.5 H CH ₃ (CH ₃ CH ₂ )(CH ₃ )C=CH- CH ₃

E1.6 H CH ₃ (cyclopropyl)CH=CH- CH ₃

E1.7 H CH ₃ (CF ₃ )CH=CH- CH ₃

E1.8 H CH ₃ (CH ₃ ) ₂ C=C(CH ₃ )- CH ₃

E1.9 H CH ₃ CH ₃ CH=C(CH ₃ )- CH ₃

E1.10 H CH ₃ CH ₃ CH ₃

El.ll H CH ₃ CH ₃ CH ₂ - CH ₃

E1.12 H CH ₃ CH ₃ CH ₂ CH ₂ - CH ₃

E1.13 H CH ₃ (CH ₃ ) ₂ CH- CH ₃

E1.14 H CH ₃ (CH ₃ ) ₂ CHCH ₂ - CH ₃

E1.15 H CH ₃ (CH ₃ ) ₃ CCH ₂ - CH ₃

E1.16 H CH ₃ cyclopropylmethyl- CH ₃

E1.17 H CH ₃ cyclobutyl CH ₃

E1.18 H CH ₃ cyclobutymethyl- CH ₃

E1.19 H CH ₃ 1 iichlorocycloprop-2-yl-methyl- CH ₃

E1.20 H CH ₃ 1 iifluorocycloprop-2-yl-methyl- CH ₃

E1.21 H CH ₃ 1 -f luorocyclopropyl-methyl- CH ₃

E1.22 H CH ₃ 1-chlorocyclopropyl-methyl- CH ₃

E1.23 H CH ₃ 1 -cyanocyclopropyl-methyl- CH ₃

E1.24 H CH ₃ 1-methylcyclopropyl-methyl- CH ₃

E1.25 H CH ₃ 1-trifluoromethylcyclopropyl-methyl- CH ₃

E1.26 H CH ₃ allyl CH ₃

E1.27 H CH ₃ propargyl CH ₃

E1.28 H CH ₃ CH ₃ C≡CCH ₂ - CH ₃

E1.29 H CH ₃ CH ₂ =C(CH ₃ )CH ₂ - CH ₃

E1.30 H CH ₃ CH ₂ =C(CH ₂ CH ₃ )CH ₂ - CH ₃

E1.31 H CH ₃ C(CH ₃ ) ₂ =C(CH ₃ )CH ₂ - CH ₃

E1.32 H CH ₃ CH(CH ₃ )=C(CH ₃ )CH ₂ - CH ₃

E1.33 H CH ₃ CH(CH ₃ )=C(CH ₂ CH ₃ )CH ₂ - CH ₃

E1.34 H CH ₃ CF ₃ CH=CHCH ₂ - CH ₃

E1.35 H CH ₃ CH ₂ =C(CF ₃ )CH ₂ - CH ₃

E1.36 H CH ₃ CH ₂ =CCICH ₂ - CH ₃ Compound R ¹ R ⁴ R ⁵ R ⁶

E1.37 H CH ₃ cyclopropyl CH ₃ CH ₂

E1.38 H CH ₃ H ₂ C=CH- CH ₃ CH ₂

E1.39 H CH ₃ (CH ₃ ) ₂ C=CH- CH ₃ CH ₂

E1.40 H CH ₃ (CH ₃ CH ₂ ) ₂ C=CH- CH ₃ CH ₂

E1.41 H CH ₃ (CH ₃ CH ₂ )(CH ₃ )C=CH- CH ₃ CH ₂

E1.42 H CH ₃ (cyclopropyl)CH=CH- CH ₃ CH ₂

E1.43 H CH ₃ (CF ₃ )CH=CH- CH ₃ CH ₂

E1.44 H CH ₃ (CH ₃ ) ₂ C=C(CH ₃ )- CH ₃ CH ₂

E1.45 H CH ₃ CH ₃ CH=C(CH ₃ )- CH ₃ CH ₂

E1.46 H CH ₃ CH ₃ CH ₃ CH ₂

E1.47 H CH ₃ CH ₃ CH ₂ - CH ₃ CH ₂

E1.48 H CH ₃ CH ₃ CH ₂ CH ₂ - CH ₃ CH ₂

E1.49 H CH ₃ (CH ₃ ) ₂ CH- CH ₃ CH ₂

E1.50 H CH ₃ (CH ₃ ) ₂ CHCH ₂ - CH ₃ CH ₂

E1.51 H CH ₃ (CH ₃ ) ₃ CCH ₂ - CH ₃ CH ₂

E1.52 H CH ₃ cyclopropylmethyl- CH ₃ CH ₂

E1.53 H CH ₃ cyclobutyl CH ₃ CH ₂

E1.54 H CH ₃ cyclobutymethyl- CH ₃ CH ₂

E1.55 H CH ₃ 1 iichlorocycloprop-2-yl-methyl- CH ₃ CH ₂

E1.56 H CH ₃ 1 iifluorocycloprop-2-yl-methyl- CH ₃ CH ₂

E1.57 H CH ₃ 1 -f luorocyclopropyl-methyl- CH ₃ CH ₂

E1.58 H CH ₃ 1-chlorocyclopropyl-methyl- CH ₃ CH ₂

E1.59 H CH ₃ 1 -cyanocyclopropyl-methyl- CH ₃ CH ₂

E1.60 H CH ₃ 1-methylcyclopropyl-methyl- CH ₃ CH ₂

E1.61 H CH ₃ 1-trifluoromethylcyclopropyl-nriethyl- CH ₃ CH ₂

E1.62 H CH ₃ allyl CH ₃ CH ₂

E1.63 H CH ₃ propargyl CH ₃ CH ₂

E1.64 H CH ₃ CH ₃ C≡CCH ₂ - CH ₃ CH ₂

E1.65 H CH ₃ CH ₂ =C(CH ₃ )CH ₂ - CH ₃ CH ₂

E1.66 H CH ₃ CH ₂ =C(CH ₂ CH ₃ )CH ₂ - CH ₃ CH ₂

E1.67 H CH ₃ C(CH ₃ ) ₂ =C(CH ₃ )CH ₂ - CH ₃ CH ₂

E1.68 H CH ₃ CH(CH ₃ )=C(CH ₃ )CH ₂ - CH ₃ CH ₂

E1.69 H CH ₃ CH(CH ₃ )=C(CH ₂ CH ₃ )CH ₂ - CH ₃ CH ₂ Compound R ¹ R ⁴ R ⁵ R ⁶

E1.103 H CH3CH2 C(CH ₃ )2=C(CH ₃ )CH2- CH ₃

E1.104 H CH3CH2 CH(CH ₃ )=C(CH ₃ )CH2- CH3

E1.105 H CH3CH2 CH(CH3)=C(CH ₂ CH ₃ )CH2- CH ₃

E1.106 H CH3CH2 CF ₃ CH=CHCH ₂ - CH ₃

E1.107 H CH3CH2 CH2=C(CF ₃ )CH ₂ - CH ₃

E1.108 H CH3CH2 CH ₂ =CCICH ₂ - CH ₃

E1.109 H CH3CH2 cyclopropyl CH3CH2

E1.110 H CH3CH2 H ₂ C=CH- CH3CH2

El.lll H CH3CH2 (CH ₃ ) ₂ C=CH- CH3CH2

E1.112 H CH3CH2 (CH ₃ CH ₂ )2C=CH- CH3CH2

E1.113 H CH3CH2 (CH ₃ CH2)(CH ₃ )C=CH- CH3CH2

E1.114 H CH3CH2 (cyclopropyl)CH=CH- CH3CH2

E1.115 H CH3CH2 (CF ₃ )CH=CH- CH3CH2

E1.116 H CH3CH2 (CH ₃ )2C=C(CH ₃ )- CH3CH2

E1.117 H CH3CH2 CH ₃ CH=C(CH ₃ )- CH3CH2

E1.118 H CH3CH2 CH ₃ CH3CH2

E1.119 H CH3CH2 CH3CH2- CH3CH2

E1.120 H CH3CH2 CH3CH2CH2- CH3CH2

E1.121 H CH3CH2 (CH ₃ ) ₂ CH- CH3CH2

E1.122 H CH3CH2 (CH ₃ ) ₂ CHCH2- CH3CH2

E1.123 H CH3CH2 (CH ₃ ) ₃ CCH2- CH3CH2

E1.124 H CH3CH2 cyclopropylmethyl- CH3CH2

E1.125 H CH3CH2 cyclobutyl CH3CH2

E1.126 H CH3CH2 cyclobutymethyl- CH3CH2

E1.127 H CH3CH2 1 ,1-dichlorocycloprop-2-yl-methyl- CH3CH2

E1.128 H CH3CH2 1 ,1-difluorocycloprop-2-yl-methyl- CH3CH2

E1.129 H CH3CH2 1 -f luorocyclopropyl-methyl- CH3CH2

E1.130 H CH3CH2 1-chlorocyclopropyl-methyl- CH3CH2

E1.131 H CH3CH2 1 -cyanocyclopropyl-methyl- CH3CH2

E1.132 H CH3CH2 1-methylcyclopropyl-methyl- CH3CH2

E1.133 H CH3CH2 1-trifluoromethylcyclopropyl-methyl- CH3CH2

E1.134 H CH3CH2 allyl CH3CH2

E1.135 H CH3CH2 propargyl CH3CH2 Compound R ¹ R ⁴ R ⁵ R ⁶

E1.136 H CH ₃ CH ₂ CH ₃ C≡CCH ₂ - CH ₃ CH ₂

E1.137 H CH ₃ CH ₂ CH ₂ =C(CH ₃ )CH ₂ - CH ₃ CH ₂

E1.138 H CH ₃ CH ₂ CH ₂ =C(CH ₂ CH ₃ )CH ₂ - CH ₃ CH ₂

E1.139 H CH ₃ CH ₂ C(CH ₃ ) ₂ =C(CH ₃ )CH ₂ - CH ₃ CH ₂

E1.140 H CH ₃ CH ₂ CH(CH ₃ )=C(CH ₃ )CH ₂ - CH ₃ CH ₂

E1.141 H CH ₃ CH ₂ CH(CH ₃ )=C(CH ₂ CH ₃ )CH ₂ - CH ₃ CH ₂

E1.142 H CH ₃ CH ₂ CF ₃ CH=CHCH ₂ - CH ₃ CH ₂

E1.143 H CH ₃ CH ₂ CH ₂ =C(CF ₃ )CH ₂ - CH ₃ CH ₂

El.144 H CH ₃ CH ₂ CH ₂ =CCICH ₂ - CH ₃ CH ₂

E1.145 CH ₃ CH ₃ CH ₃ CH ₃

E1.146 CH ₃ CH ₃ CH ₃ CH ₂ - CH ₃

E1.147 CH ₃ CH ₃ cyclopropylmethyl- CH ₃

E1.148 CH ₃ CH ₃ CH ₂ =C(CH ₃ )CH ₂ - CH ₃

E1.149 CH ₃ CH ₃ CH ₂ CH ₃ CH ₃

E1.150 CH ₃ CH ₃ CH ₂ CH ₃ CH ₂ - CH ₃

E1.151 CH ₃ CH ₃ CH ₂ cyclopropylmethyl- CH ₃

E1.152 CH ₃ CH ₃ CH ₂ CH ₂ =C(CH ₃ )CH ₂ - CH ₃

E1.153 CH ₃ CH ₃ CH ₃ CH ₃ CH ₂

E1.154 CH ₃ CH ₃ CH ₃ CH ₂ - CH ₃ CH ₂

E1.155 CH ₃ CH ₃ cyclopropylmethyl- CH ₃ CH ₂

E1.156 CH ₃ CH ₃ CH ₂ =C(CH ₃ )CH ₂ - CH ₃ CH ₂

E1.157 CH ₃ CH ₃ CH ₂ CH ₃ CH ₃ CH ₂

E1.158 CH ₃ CH ₃ CH ₂ CH ₃ CH ₂ - CH ₃ CH ₂

E1.159 CH ₃ CH ₃ CH ₂ cyclopropylmethyl- CH ₃ CH ₂

E1.160 CH ₃ CH ₃ CH ₂ CH ₂ =C(CH ₃ )CH ₂ - CH ₃ CH ₂

E1.161 H cyclopropyl- CH ₃ CH ₃

E1.162 H cyclopropyl- CH ₃ CH ₂ - CH ₃

E1.163 H cyclopropyl- CH ₃ CH ₂ CH ₂ - CH ₃

E1.164 H cyclopropyl- cyclopropyl CH ₃

E1.165 H cyclopropyl- cyclopropylmethyl- CH ₃

Table 1.2: This table discloses 165 specific compounds of formula (I) wherein R ² is methyl, R ³ is hydrogen and wherein the values of R\ R ⁴ , R ⁵ and R ⁶ are as defined in Table Z.1. Table 1.3: This table discloses 165 specific compounds of formula (I) wherein R ² is methyl, R ³ is methyl and wherein the values of R\ R ⁴ , R ⁵ and R ⁶ are as defined in Table Z.1.

Table 1.4: This table discloses 165 specific compounds of formula (I) wherein R ² is methyl, R ³ is ethyl and wherein the values of R , R ⁴ , R ⁵ and R ⁶ are as defined in Table Z.1.

Table 1.5: This table discloses 165 specific compounds of formula (I) wherein R ² is methyl, R ³ is propyl and wherein the values of R , R ⁴ , R ⁵ and R ⁶ are as defined in Table Z.1. Table 1.6: This table discloses 165 specific compounds of formula (I) wherein R ² is chloro, R ³ is methyl and wherein the values of R , R ⁴ , R ⁵ and R ⁶ are as defined in Table Z.1.

Table 1.7: This table discloses 165 specific compounds of formula (I) wherein R ² is bromo, R ³ is methyl and wherein the values of R , R ⁴ , R ⁵ and R ⁶ are as defined in Table Z.1.

Table 1.8: This table discloses 165 specific compounds of formula (I) wherein R ² is fluoro, R ³ is methyl and wherein the values of R , R ⁴ , R ⁵ and R ⁶ are as defined in Table Z.1.

Table 1.9: This table discloses 165 specific compounds of formula (I) wherein R ² is methoxy, R ³ is methyl and wherein the values of R , R ⁴ , R ⁵ and R ⁶ are as defined in Table Z.1.

Table 1.10: This table discloses 165 specific compounds of formula (I) wherein R ² is chloro, R ³ is ethyl and wherein the values of R , R ⁴ , R ⁵ and R ⁶ are as defined in Table Z.1. Table 1.11 : This table discloses 165 specific compounds of formula (I) wherein R ² is bromo, R ³ is ethyl and wherein the values of R , R ⁴ , R ⁵ and R ⁶ are as defined in Table Z.1.

Table 1.12: This table discloses 165 specific compounds of formula (I) wherein R ² is fluoro, R ³ is ethyl and wherein the values of R , R ⁴ , R ⁵ and R ⁶ are as defined in Table Z.1.

Table 1.13: This table discloses 165 specific compounds of formula (I) wherein R ² is methoxy, R ³ is ethyl and wherein the values of R , R ⁴ , R ⁵ and R ⁶ are as defined in Table Z.1.

Table 1.14: This table discloses 165 specific compounds of formula (I) wherein R ² is methyl, R ³ is isopropyl and wherein the values of R , R ⁴ , R ⁵ and R ⁶ are as defined in Table Z.1.

Table 1.15: This table discloses 165 specific compounds of formula (I) wherein R ² is methyl, R ³ is cyclopropyl and wherein the values of R , R ⁴ , R ⁵ and R ⁶ are as defined in Table Z.1. Table 1.16: This table discloses 165 specific compounds of formula (I) wherein R ² is methyl, R ³ is difluoromethyl and wherein the values of R , R ⁴ , R ⁵ and R ⁶ are as defined in Table Z.1. Table 1.17: This table discloses 165 specific compounds of formula (I) wherein R ² is methyl, R ³ is trifluoromethyl and wherein the values of R , R ⁴ , R ⁵ and R ⁶ are as defined in Table Z.1. Table 1.18: This table discloses 165 specific compounds of formula (I) wherein R ² is methyl, R ³ is isobutyl and wherein the values of R , R ⁴ , R ⁵ and R ⁶ are as defined in Table Z.1.

Table 1.19: This table discloses 165 specific compounds of formula (I) wherein R ² is methyl, R ³ is cyclopropylmethyl- and wherein the values of R , R ⁴ , R ⁵ and R ⁶ are as defined in Table Z.1.

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 60 ppm, 20 ppm or 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).

Throughout this description, temperatures are given in degrees Celsius and "m.p." means melting point. LC/MS means Liquid Chromatography Mass Spectroscopy and the description of the apparatus and the methods are:

Method A:

Spectra were recorded on a Mass Spectrometer from Waters (SQD, SQDII Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive and negative ions), Capillary: 3.00 kV, Cone range: 30 V, Extractor: 2.00 V, Source Temperature: 150°C, Desolvation Temperature: 350°C, Cone Gas Flow: 50 l/h, Desolvation Gas Flow: 650 l/h, Mass range: 100 to 900 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment, diode-array detector and ELSD detector. Column: Waters UPLC HSS T3, 1.8 μητι, 30 x 2.1 mm, Temp: 60 °C, DAD Wavelength range (nm): 210 to 500, Solvent Gradient: A = water + 5% MeOH + 0.05 % HCOOH, B= Acetonitrile + 0.05 % HCOOH, gradient: 10-100% B in 1.2 min; Flow (ml/min) 0.85.

Method B:

Spectra were recorded on a Mass Spectrometer from from Agilent Technologies (6410 Triple Quadruple Mass Spectrometer) equipped with an electrospray source, Polarity: positive or negative ions, Scan Type: MS2 Scan, Capillary (kV): 4.00, Fragmentor (V): 100.00, Gas Temperature (°C): 350, Gas Flow (L/min): 11 , Nebulizer Gas (psi): 45, Mass range: 1 10 to 1000 Da and a 1200 Series HPLC from Agilent:, Temp: 40 °C, DAD Wavelength range (nm): 210 to 400, Column: KINETEX EVO C18, 2.4 μπι, 50 x 4.6 mm, Solvent Gradient: A = water with 0.1 % formic acid : Acetonitrile: 95:5 (v/v), B= Acetonitrile with 0.1 % formic acid, gradient: 10-100% B in 0.9 min then 100% B for 0.9 min; Flow (ml/min) 1.85.

Where necessary, enantiomerically pure final compounds may be obtained from racemic materials as appropriate via standard physical separation techniques, such as reverse phase chiral chromatography, or through stereoselective synthetic techniques, eg, by using chiral starting materials. 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 water to 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 mi) i with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that n 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 ide) 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 polyvinylalcohol, 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.

List of Abbreviations: AIBN = azobisisobutyronitrile

CCU = carbon tetrachloride

CDCI3 = chloroform-d

°C = degrees Celsius DMF = dimethylformamide

Dppf = 1 , 1 '-bis(diphenylphosphino)ferrocene

d = doublet

h = hour(s)

HCI = hydrochloric acid

M = molar

min = minutes

MHz = mega hertz

mp = melting point

ppm = parts per million

RT = room temperature

s = singlet

t = triplet

THF = tetrahydrofuran

LC/MS = Liquid Chromatography Mass Spectrometry (description of the apparatus and the methods used for LC/MS analysis are given above)

Preparation examples: Example 1 (compound A-10 in table A): This example illustrates the preparation of [2-methyl-6-(4- methyl-5-oxo-tetrazol-1-yl)phenyl]methyl N-[3-cyclopropyl-2-methoxyimino-1-methyl- propylidene]propanehydrazonate

Step 1: Preparation of 1-bromo-3-isocyanato-2-m ethyl-benzene

To a vigorously stirred solution of 3-bromo-2-methylaniline (5.0 g, 26.9 mmol) in a 1 :1 mixture of dichloromethane (67.2 mL) and sodium bicarbonate (80.6 mL, 1 .15 M) was added dropwise a solution of triphosgene (2.79 g, 9.41 mmol, 0.35 equiv) in (15 mL) at 0°C. The reaction mixture was stirred until no more gas formation was observed. The organic and water phases were separated. The aqueous phase was extracted with dichloromethane, and the combined organic layer was washed with brine, dried over Na2S04 and concentrated under reduced pressure to give 1-bromo-3- isocyanato-2-methyl-benzene (5.70 g, 98 %) as a brown liquid that was used in the next step without further purification. Ή NMR (400 MHz, CDCIs) δ 7.40 (dd, J = 7.9, 1.5 Hz, 1 H), 7.05 (dd, J = 8.0, 1.5 Hz, 1 H), 7.00 (t, J = 7.9 Hz, 1 H), 2.43 (s, 3H). LC (method A): 0.99 min. Step 2: Preparation of 4-(3-bromo-2-methyl-phenyl)-1 H-tetrazol-5-one

To 1-bromo-3-isocyanato-2-methyl-benzene (2.60 g, 12.3 mmol) was added trimethylsilyl azide (5.14 mL, 36.8 mmol, 3 equiv) at room temperature under Ar. The reaction mixture was heated to 100°C for 5 6 h, behind a shield. After cooling to room temperature, the reaction mixture was poured into 10% aq sodium acetate solution and ethylacetate. The organic and water phases were separated and the aqueous phase extracted with ethylacetate. The combined organic layer was washed with 10% aq sodium acetate solution and brine, dried over Na2S04 and concentrated under reduced pressure to give 4-(3-bromo-2-methyl-phenyl)-1 H-tetrazol-5-one (3.24 g, 93 %) that was used in the next step 10 without further purification. Ή NMR (400 MHz, DMSO-de) δ 14.71 (s, 1 H), 7.83 (dd, J = 8.1 , 1.3 Hz, 1 H), 7.49 (dd, J = 7.9, 1.3 Hz, 1 H), 7.35 (t, J = 8.0 Hz, 1 H), 2.23 (s, 3H). LC (method A): 1.15 min, [M+H] ⁺ = 255.

Step 3: Preparation of 1-(3-bromo-2-methyl-phenyl)-4-methyl-tetrazol-5-one

15

To a solution of 4-(3-bromo-2-methyl-phenyl)-1 H-tetrazol-5-one (55 g, 215.6 mmol) in

dimethylformamide (215 mL) was added K2CO3 (47.68 g, 345.0 mmol, 1.6 equiv) and iodomethane (20.8 mL, 323.4 mmol, 1 .5 equiv) at room temperature under Ar. The temperature was kept at 20-

20 25°C with a water bath (slightly exothermic reaction). After reaction completion, water was added until no more precipitate was formed. The precipitate was filtered off, washed with ice-cooled water and dissolved in dichloromethane. The aqueous phase was extracted with dichloromethane. The combined organic layer was washed with brine, dried over Na2S04 and concentrated under reduced pressure to give 1-(3-bromo-2-methyl-phenyl)-4-methyl-tetrazol-5-one (60.5 g, 94 %) as a brown solid.

25 Ή NMR (400 MHz, CDCI3) 5 7.71 (dd, J = 8.1 , 1 .3 Hz, 1 H), 7.30 (dd, J = 7.9, 1 .3 Hz, 1 H), 7.21 (t, J = 8.1 Hz, 1 H), 3.73 (s, 3H), 2.33 (s, 3H). LC: 1.30 min (method A), [M+H] ⁺ = 271. Step 4: Preparation of 1-[3-bromo-2-(bromomethyl)phenvn-4-methyl-tetrazol-5-one

H 3

To a suspension of 1-(3-bromo-2-methyl-phenyl)-4-nriethyl-tetrazol-5-one (10 g, 35.3 mmol) and N- bromosuccinimide (7.05 g, 38.8 mmol, 1.1 equiv) in CCU (100 mL) were added at 70°C AIBN (592 mg, 3.53 mmol, 0.1 equiv) and benzoyl peroxide (570 mg, 1.77 mmol, 0.05 equiv). After reaction completion, the reaction mixture was cooled to room temperature and quenched with sodium thiosulfate. The separated organic phase was concentrated in vacuum, then poured into water and dichloromethane, the layers were separated and the organic phase was washed with brine, dried over Na2S04 and concentrated under reduced pressure. The residue was purified by flash chromatography to give 1-[3-bromo-2-(bromomethyl)phenyl]-4-methyl-tetrazol-5-one (10.92 g, 89 %). 1 H NMR (400 MHz, CDCI3) δ 7.80 (dd, J = 7.7, 1.7 Hz, 1 H), 7.47 - 7.34 (m, 2H), 4.75 (s, 2H), 3.79 (s, 3H). LC: 0.92 min (method A), [M+H] ⁺ = 349.

Step 5: Preparation of 2-bromo-6-(4-methyl-5-oxo-tetrazol-1-yl)benzaldehvde H 3

To a solution of 4-methylmorpholine N-oxide (3.5 g, 29 mmol, 4.0 equiv) in THF (36 mL) was added 1- [3-bromo-2-(bromomethyl)phenyl]-4-methyl-tetrazol-5-one (2.5 g, 7.2 mmol). The reaction mixture was heated at reflux for 2 h. Then, it was quenched with water, and extracted with ethylacetate. The combined organic layer was washed with brine, dried over Na2S04 and concentrated under reduced pressure. The residue was purified by flash chromatography to give 2-bromo-6-(4-methyl-5-oxo- tetrazol-1-yl)benzaldehyde (1.64 g, 81 %) as a white powder. Ή NMR (400 MHz, CDCI ₃ ) 5 10.31 (s, 1 H), 7.81 (dd, J = 7.6, 1.7 Hz, 1 H), 7.68 - 7.45 (m, 2H), 3.71 (s, 3H). LC: 0.77 min (method A), [M+H] ⁺ = 285. Step 6: Preparation of 2-methyl-6-(4-methyl-5-oxo-tetrazol-1-yl)benzaldehvde

To a stirred solution of 2-bromo-6-(4-methyl-5-oxo-tetrazol-1-yl)benzaldehyde (2.98 g, 10.5 mmol) in dioxane (105 mL) was added K2CO3 (2.91 g, 21.1 mmol, 2 equiv), trimethylboroxine (2.97 mL, 21.1 mmol, 2 equiv), 3A molecular sieves and Pd(dppf)Cl2 (373 mg, 0.526 mmol, 0.05 equiv) under Ar. The reaction mixture was stirred at 100°C for 2 h. After cooling to room temperature, the reaction mixture was quenched with saturated aqueous NaHCCh solution and extracted with ethyl acetate, at pH 8. The organic layer was washed with brine, dried over Na2S04 and concentrated under reduced pressure. The residue was purified by flash chromatography to give 2-methyl-6-(4-methyl-5-oxo-tetrazol-1- yl)benzaldehyde (3.0 g, 91 %) as a white powder. Ή NMR (400 MHz, CDCI3) δ 10.20 (s, 1 H), 7.59 (t, J = 7.8 Hz, 1 H), 7.44 - 7.37 (m, 2H), 3.72 (s, 3H), 2.69 (s, 3H). LC: 0.73 min (method A), [M+H] ⁺ = 219. Step 7: Preparation of 1-[2-(hvdroxymethyl)-3-methyl-phenyll-4-methyl-tetrazol-5-on e

To a solution of 2-methyl-6-(4-methyl-5-oxo-tetrazol-1-yl)benzaldehyde (14.1 mmol, 3.23 g) in ethanol (42 mL) at RT was added sodium borohydride (14.8 mmol, 0.559 g). The reaction mixture was stirred for 20 minutes and then quenched by slowly adding a2.5M aqueous solution of NH4CI. The resulting mixture was concentrated under reduced pressure to around a third of the original volume. Then ethylacetate and aqueous NaHCCh 1 M were added. The layers were separated and the aqueous one extracted once more with ethylacetate. The combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated in vacuo to give 1-[2-(hydroxymethyl)-3-methyl-phenyl]-4- methyl-tetrazol-5-one as a dark grey solid. The crude residue was used for the next step without further purification.

LC/MS (Method A) retention time = 0.77 min; [M+Na ⁺ ] = 243 Step 8: Preparation of 1-[2-(bromomethv0-3-methyl-phenvn-4-methyl-tetrazol-5-one

To a solution of 1-[2-(hydroxymethyl)-3-methyl-phenyl]-4-methyl-tetrazol-5-on e (1.7 g, 7.7 mmol) in dichloromethane at 0 °C was added tribromophosphane (1.1 equiv., 8.5 mmol) and the reaction mixture was allowed to stir at 0°C for 30 minutes. The reaction mixture was then diluted with dichloromethane, washed with 10% sodium metabisulphite and then with water. The organic layer was then dried over sodium sulphate, filtered and concentrated under reduced pressure to afford 1-[2- (bromomethyl)-3-methyl-phenyl]-4-methyl-tetrazol-5-one as a white solid.

LC/MS (Method A) retention time = 0.89 min; [M+H ⁺ ] = 283 and 285

Step 9: Synthesis of ethyl 2-(cvclopropylmethvD-3-oxo-butanoate

Bromomethylcyclopropane was added to a mixture of ethyl acetoacetate, potassium iodide, potassium carbonate and tetrabutylammonium bromide in DMF at 50 °C. The reaction mixture was then heated at 70 °C for 16h. The reaction mixture was then diluted with water and extracted with diethyl ether. The combined organic layers were dried over Na2S04, filtered and concentrated under reduced pressure. The crude residue was purified by flash chromatography to give 2-(cyclopropylmethyl)-3- oxo-butanoate as a slightly yellow liquid.

2-(cyclopropylmethyl)-3-oxo-butanoate can also be purchased from Cambridge Chemicals.

Step 10: Synthesis of 4-cvclopropyl-3-hvdroxyimino-butan-2-one

The 2-(cyclopropylmethyl)-3-oxo-butanoate was dissolved in 10% KOH aqueous solution and cooled down to 0 °C. Sodium nitrite was then slowly added and the resulting mixture was warmed to RT and stirred overnight. The reaction mixture was again cooled down to 0 °C and 10% H2SO4 solution was added dropwise while keeping internal temperature under 10 °C. Evolution of CO2 was observed once 2 equivalents of H2SO4 solution was added. The reaction mixture was stirred at ca. 5 °C until CO2 evolution stopped (1 h). The reaction mixture was then diluted with water and extracted with ethyl acetate. The combined organic layers were dried over Na2S04, filtered and concentrated under reduced pressure. The crude residue was purified by flash chromatography to give 4-cyclopropyl-3- hydroxyimino-butan-2-one as a white solid.

LC/MS (Method A) retention time = 0.73 min; [M+H ⁺ ] = 142

Step 11: Synthesis of 4-cvclopropyl-3-methoxyimino-butan-2-one

To a solution of 4-cyclopropyl-3-hydroxyimino-butan-2-one (2 g, 14.2 mmol) in DMF (71 mL) at 0 °C was added portion wise sodium hydride 60% in mineral oil (595 mg, 14.9 mmol). After gas evolution ceased, iodomethane (0.98 mL, 15.6 mmol, 1.1 eq), was added dropwise while maintaining the reaction mixture at 0°C. The resulting yellow solution was stirred 1 h20 at 0°C at which point it was quenched carefully by the addition of water. The aqueous phase was extracted with diethyl ether and the combined organic layers were washed generously with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford 4-cyclopropyl-3-methoxyimino-butan-2-one as a yellow oil. The crude residue was used for the next step without further purification.

LC/MS (Method A) retention time = 0.99 min; product did not ionized

Ή NMR (400 MHz, CDCI3) δ: 4.05 (s, 3H), 2.97 (s, 1 H), 2.89 (s, 1 H), 2.38 (s, 3H), 0.83-0.95 (m, 1 H), 0.31-0.43 (m, 2H), 0.1 1-0.20 (m, 2H)

Step 12: Synthesis of N-[3-cvclopropyl-2-methoxyimino-1-methyl-propylidenelaminolp ropanamide

To a solution of propanehydrazide (330 mg, 3.75 mmol, 1 eq) in ethanol (1 1.2 mL), at RT under argon, was added 4-cyclopropyl-3-methoxyimino-butan-2-one (581 mg, 3.75 mmol, 1 eq) followed by acetic acid (0.107 mL, 1.87 mmol, 0.5 eq). The resulting colourless solution was stirred at 70°C for 16h. The crude reaction mixture was then concentrated under reduce pressure. The residue obtained was partitioned between dichloromethane and a solution of saturated NaHCC^. The aqueous layer was extracted with dichloromethane and the combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The solid obtained was crystallized from cold pentane and few drops of ether to afford the desired product as a white solid.

LC/MS (Method A) retention time = 0.97 min; [M+H+] = 226

Ή NMR (400 MHz, CDCIs) δ: 8.47 (s, 1 H), 3.91-4.00 (m, 3H), 2.70 (q, J=7.7 Hz, 2H), 2.50-2.60 (m, 2H), 2.05 (s, 3H), 1 .21 (t, J=7.5 Hz, 3H), 0.95-1.04 (m, 1 H), 0.37-0.43 (m, 2H), 0.16-0.23 (m, 2H)

Step 13: Synthesis of [2-methyl-6-(4-methyl-5-oxo-tetrazol-1-vnphenyllmethyl-N-[3- cyclopropyl-2- m ethoxyim i no- 1 -m ethyl-propylidenel propanehvd razonate

To a solution of 1-[2-(bromomethyl)-3-methyl-phenyl]-4-methyl-tetrazol-5-one (250 mg, 0.883 mmol, 1 eq) in DMF (7 mL), at RT under argon, was added potassium carbonate (250 mg, 1.77 mmol, 2 eq) followed by N-[(E)-[(2E)-3-cyclopropyl-2-methoxyimino-1-methyl-propylide ne]amino]propanamide (199 mg, 0.883 mmol, 1 eq). The resulting colorless solution was stirred at 30°C for 16h and then at 50°C for an additional 2h. The reaction mixture was then quenched with water, and the organic layer was extracted with dichloromethane. The combined organic layers were washed with water, brine and then dried on sodium sulfate and concentrated under reduced pressure. The residue obtained was purified by column chromatography (0-10% gradient of ethylacetate in a 1 :1 mixture of cyclohexane and dichloromethane containing 1 % triethylamine). The solid obtained was then crystallized from cold pentane (1 mL) to afford the desired product as a white solid.

LC/MS (Method A) retention time = 1.26 min; [M+H+] = 428 mp = 74-76°C

Ή NMR (400 MHz, CDCI3) δ: 7.34-7.45 (m, 2H), 7.23-7.26 (m, 1 H), 5.22 (s, 2H), 3.97 (s, 3H), 3.69 (s, 3H), 2.60 (d, J=7.0 Hz, 2H), 2.51 (s, 3H), 2.44 (q, J=7.5 Hz, 2H), 2.08 (s, 3H), 1 .03 (t, J=7.5 Hz, 4H), 0.34-0.41 (m, 2H), 0.16-0.23 (m, 2H) Table A provides compounds of the present invention prepared by analogous procedures, from appropriate starting materials. The skilled person would understand that the compounds of formula (I) may exist as E and/or Z isomers as described hereinbefore. Where mentioned the specific geometric configuration is not considered to be limiting.

Preferably, the compound according to formula (I) is selected from a compound A-1 to A-63 listed in Table A (below). able A: Physical data of compounds of formula I

Biological examples

Alternaria solani I tomato / leaf disc (early blight)

Tomato leaf disks cv. Baby 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 2 days after application. The inoculated leaf disks are incubated at 23 °C / 21 °C (day/night) and 80% rh under a light regime of 12/12 h (light/dark) 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 on untreated check disk leaf disks (5 - 7 days after application). The following compounds gave at least 80% control of Alternaria solani at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: A-2, A-4, A-5, A-6, A-8, A-9, A-13, A-14, A-15, A-16, A-18, A-19, A-20, A-21 , A-23, A-25, A-26, A-29, A-30, A-31 , A-32, A-39, A-41 , A-42, A-48, A-52, A-55

Botryotinia fuckeliana (Botrytis cinerea) I 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:

A-10, A-16, A-18, A-19, A-20, A-21 , A-22, A-23, A-25, A-26, A-27, A-29, A-30, A-34, A-36, A-37, A- 39, A-40, A-41 , A-42, A-49, A-50, A-51 , A-58, A-59, A-60, A-63

Glomerella lagenarium (Colletotrichum lagenarium) I 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:

A-2, A-3, A-5, A-6, A-7, A-8, A-9, A-10, A-13, A-14, A-15, A-16, A-18, A-19, A-20, A-21 , A-22, A-23, A-25, A-26, A-27, A-28, A-29, A-30, A-32, A-33, A-37, A-39, A-40, A-41 , A-42, A-43, A-46, A-49, A- 50, A-51 , A-53, A-55, A-56, A-58, A-59, A-60, A-62, A-63

Blumeria graminis f. sp. tritici (Erysiphe graminis f. sp. tritici) I 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. triticiai 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

A-2, A-3, A-5, A-6, A-7, A-8, A-9, A-10, A-1 1 , A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21 , A-22, A-23, A-26, A-27, A-28, A-29, A-30, A-32, A-33, A-34, A-36, A-37, A-39, A-40, A-41 , A-42, A- 43, A-46, A-48, A-49, A-50, A-51 , A-52, A-55, A-56

Fusarium culmorum I liquid culture (Head blight)

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 3-4 days after application.

The following compounds gave at least 80% control of Fusarium culmorum at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

A-10

Phaeosphaeria nodorum (Septoria nodorum) I 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:

A-2, A-5, A-6, A-8, A-9, A-14, A-15, A-16, A-18, A-19, A-23, A-26, A-27, A-29, A-30, A-32, A-33, A- 34, A-36, A-37, A-39, A-41 , A-42, A-43, A-46, A-48, A-49, A-50, A-51 , A-52, A-55, A-56

Monographella nivalis (Microdochium nivale) I 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:

A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-1 1 , A-12, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21 , A-22, A-23, A-25, A-26, A-27, A-28, A-29, A-30, A-31 , A-32, A-33, A-34, A-35, A-36, A- 37, A-38, A-39, A-40, A-41 , A-42, A-43, A-46, A-47, A-48, A-49, A-50, A-51 , A-52, A-58, A-59, A-60, A-62, A-63

Mycosphaerella arachidis (Cercospora arachidicola) I 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:

A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21 , A-22, A-23, A-25, A-26, A-27, A-28, A-29, A-30, A-31 , A-32, A-33, A-34, A-36, A-37, A-38, A-39, A- 40, A-41 , A-42, A-43, A-46, A-48, A-49, A-50, A-51 , A-52

Phakopsora pachyrhizi I 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:

A-6, A-30

Plasmopara viticola I grape / leaf disc preventative (late blight)

Grape vine leaf disks are placed on water 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 disks are incubated at 19 °C and 80% 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 (6 - 8 days after application). The following compounds gave at least 80% control of Plasmopara viticola at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

A-2, A-29, A-32, A-42

Puccinia recondita f. sp. tritici I 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:

A-2, A-5, A-9, A-18, A-19, A-20, A-21 , A-26, A-27, A-30, A-32, A-33, A-34, A-36, A-37, A-39, A-41 , A-42, A-46, A-51 , A-52, A-55

Puccinia recondita f. sp. tritici I 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:

A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-1 1 , A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21 , A-23, A-25, A-26, A-27, A-29, A-30, A-31 , A-32, A-33, A-34, A-36, A-37, A-38, A-39, A-40, A- 41 , A-42, A-43, A-46, A-48, A-49, A-50, A-51 , A-52, A-55, A-56

Magnaporthe grisea (Pyricularia oryzae) I 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:

A-2, A-5, A-10, A-13, A-15, A-16, A-18, A-19, A-20, A-21 , A-23, A-25, A-26, A-27, A-29, A-30, A-31 , A-32, A-33, A-36, A-37, A-39, A-40, A-41 , A-42, A-46, A-48, A-49, A-50, A-52, A-55, A-56

Pyrenophora teres I barley / leaf disc preventative (Net blotch)

Barley leaf segments cv. Hasso are placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water. The leaf segmens are inoculated with a spore suspension of the fungus 2 days after application. The inoculated leaf segments are incubated at 20 °C and 65% 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 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 Pyrenophora teres at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-1 1 , A-14, A-15, A-16, A-18, A-19, A-20, A-21 , A-26, A-27, A-29, A-30, A-31 , A-32, A-33, A-34, A-36, A-37, A-39, A-40, A-41 , A-42, A-43, A-46, A-48, A- 49, A-50, A-51 , A-52, A-55

Thanatephorus cucumeris (Rhizoctonia solani) I liquid culture (foot rot, dam ping-off)

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 the test compounds 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 Thanatephorus cucumeris at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

A-2

Sclerotinia sclerotiorum I 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:

A-32, A-37, A-42 Mycosphaerella graminicola (Septoria tritici, field strain bearing the G143A mutation of the cytochrome b subunit of the ubiquinol-cytochrome-c reductase complex) / 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:

A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-1 1 , A-13, A-14, A-15, A-16, A-17, A-18, A-19, A-20, A-21 , A-22, A-23, A-25, A-26, A-27, A-28, A-29, A-30, A-31 , A-32, A-33, A-34, A-35, A-36, A-37, A- 38, A-39, A-40, A-41 , A-42, A-43, A-46, A-48, A-49, A-50, A-51 , A-52, A-53, A-55, A-56, A-57, A-58, A-59, A-60, A-62

Mycosphaerella graminicola (Septoria tritici) I 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:

A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-13, A-14, A-16, A-17, A-18, A-19, A-20, A-21 , A-22, A-23, A-25, A-26, A-27, A-28, A-29, A-30, A-31 , A-32, A-33, A-34, A-36, A-37, A-39, A-40, A-41 , A- 42, A-43, A-46, A-48, A-49, A-50, A-51 , A-52, A-55, A-56, A-59, A-60, A-62, A-63

Comparative data:

The biological activity of compounds A-5, A-10, A-16, A-18 and A-30 of the invention are compared to the reference compounds X-1 and X-2. Reference compounds X-1 and X-2 are specifically disclosed on page 460 of WO 2016/088747.

The data are presented as the percentage of disease control of each compound for the biological tests described above. The testing rates of each biological test is specifically described in table C below. Table C: Comparative Data

Reference Compound X-1 Reference Compound X-2 WO 2016/088747 WO 2016/088747