RU2796397C9 - 4-substituted phenylamine derivatives and their use to protect crops against undesirable phytopathogenic microorganisms - Google Patents

Abstract

FIELD: organic chemistry.

SUBSTANCE: derivatives of 4-substituted phenylamine of general formula (I) and agronomically acceptable salts of these compounds, where R¹ is hydrogen; R² is C_2-8alkyl; R³ is C_1-6alkyl; where each R² and R³ may be optionally substituted with one or more groups selected from the group consisting of X and R'; R⁴, R⁵, R⁶ and R⁷ are independently selected from the group consisting of hydrogen, X, CN, S(O)_nR'' ,OR'', C_1-8-alkyl and C_3-8-cycloalkyl; and all groups above may be optionally substituted with one or more groups selected from the group consisting of X and R'; R⁸ and R⁹ are independently selected from the group consisting of hydrogen, X, CN, (C=O)-R'', C_1-6-alkyl and C_1-6-alkoxy; and all groups above may be substituted with one or more groups selected from the group consisting of X and R' or R⁸ and R⁹ together with the atoms to which they are attached may form a group =C(R'R'''), =NR'''; A is selected from the group consisting of fused or non-fused C₆-₁₀aryl and pyridinyl; this ring A is optionally substituted with one or more R¹⁰ groups; where R¹⁰ is selected from the group containing hydrogen, X, CN, NO₂, NR'₂, S(O)_nR'', C_1-8alkyl, C_1-8haloalkyl, C_1-8alkoxy, C_1-8alkylthio, C_1-8haloalkoxy, C_1-8haloalkylthio, C_3-8cycloalkyl; and where each R⁸, R⁹ and R¹⁰ may be optionally substituted with one or more groups selected from the group consisting of X and R'; where X is a halogen; R' is selected from the groups consisting of hydrogen, straight or branched chain C _1-6 -alkyl and cyclic C _3-6 -alkyl, where each group R' optionally substituted with one or more Xs; R'' selected from groups consisting of hydrogen, NR'₂, OR' and unbranched or branched chain C_1-12alkyl; each R group'' optionally substituted with one or more groups selected from the group consisting of X, R', OR', CN and phenyl which is optionally substituted with one or more R'; R''' is selected from the groups consisting of hydrogen and unbranched or branched C_1-6alkyl; and all groups above may be substituted with one or more X; m and n are integers, where n=0, 1 or 2; and m=1 or 2. The invention also relates to a composition, the use of a compound represented by formula (I) or a composition based on it, a method for controlling or preventing infection of useful plants with phytopathogenic fungi in cultivated crops and/or horticultural crops.

EFFECT: effective protection against phytopathogenic microorganisms of beneficial plants in cultivated crops and/or horticultural crops provided by a compound of general formula (I) or a composition based on it.

13 cl, 3 tbl, 32 ex

(I)

Description

FIELD OF THE INVENTION

The invention relates to compounds aimed at protecting crops from unwanted phytopathogenic fungi. More precisely, the subject of this invention relates to derivatives of 4-substituted phenylamine, which are used to protect crops from unwanted phytopathogenic fungi.

BACKGROUND OF THE INVENTION

The control of crop damage caused by phytopathogenic microorganisms is very important in achieving high crop performance. For example, plant diseases affecting ornamental plants, vegetables, field crops, cereals and fruit crops can significantly reduce yields and thereby increase their cost to the consumer. Many products for the control of such diseases are commercially available. The need for new compounds that are more effective, less expensive, less toxic, environmentally safer and/or have different modes of action remains relevant. Certain derivatives of phenylamine are described in the literature as microbiologically active components of pesticides. For example, WO 2000046184, WO 2003093224, WO 2003024219, WO 2005089547, WO 2005120234 and US 20110082036 describe the use of phenylamine derivatives, especially phenylamidine, alone or as part of a compound as fungicides. Certain phenyl benzamide compounds, the method for producing such compounds, and their use in controlling unwanted microorganisms are described in WO 2004005242.

US 4,173,637 describes phenylurea compounds and compositions containing such compounds as insecticides. JP 08291146 describes N-substituted phenylsulfonamide compounds which have good herbicidal activity, especially herbicides for irrigated fields. WO 2008110314 describes fluoroalkyl phenylamidines as fungicidal compounds, a method for their manufacture, and a method for protecting seeds from undesirable microorganisms using such compounds. Another PCT publication WO 2011095462 describes phenylamine derivatives, including carboxamides, their manufacturing process and insecticidal, acaricidal, nematicidal or molluscicide compositions containing such compounds. Certain amidine compounds exhibit antifungal activity against the pathogenic fungi Candida, Aspergillus and Trichophyton, being pharmaceutically useful, and are described in WO 2013018735.

The efficiency of the phenylamine derivatives described in the prior art is good, but there are still points that one would like to see in different cases. Therefore, there is always a great interest in agriculture in the use of new pesticide compounds to prevent and/or control the development of microorganisms, such as fungal or bacterial pathogens, or pests resistant to known active ingredients. Therefore, there is great interest in the use of new compounds that are more active than those already known, in order to reduce the amount of active compound used, but with at least the same efficiency as the known compounds.

We have found a new family of compounds that have the above effects or benefits. The new family of compounds, namely the 4-substituted phenylamine derivatives, in which the phenyl rings are substituted in accordance with the invention, therefore provide an unexpected and significantly higher activity against undesirable microorganisms, such as fungal or bacterial pathogens or pests.

BRIEF DESCRIPTION OF THE INVENTION

The invention relates to the latest and developed derivatives of 4-substituted phenylamine formula (I),

where the definition of substituents is defined with the following detailed description.

The 4-substituted phenylamine derivatives of the present invention are new and innovative even in view of US 8080688 and the corresponding EP application No. 2120558.

US 8,080,688 describes 3,4-substituted phenoxyphenyl amidines represented by the general formula

where two phenyl rings are linked by "-O-".

See Chart I, steps (a-f) on pages 18-25 compound (I), and steps (g-j) on pages 27-30 compound (I) of US 8080688. See also examples in Table IV on pages 48-49.

However, in the embodiment of the invention on page 18, par. 5 and claim 4, Applicant US 8080688 describes 3,4-substituted benzylphenyl amidines. The list of 3,4-substituted benzylphenyl amidines compounds provided in US 8,080,688 is as follows:

N'-[4-(2,3-dihydro-1H-inden-5-ylmethyl)-2,5-dimethylphenyl]-N-ethyl-N-methylimidoformamide,

N'-{4-[(3,3-dimethyl-2,3-dihydro-1H-inden-5-yl)methyl]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide,

N'-[4-(3-chloro-4-isopropylbenzyl)-2,5-dimethylphenyl]-N-ethyl-N-methylimidoformamide,

N'-[4-(3-chloro-4-tert-butylbenzyl)-2,5-dimethylphenyl]-N-ethyl-N-methylimidoformamide,

N-ethyl-N'-{4-[(3-hydroxy-3-methyl-2,3-dihydro-1H-inden-5-yl)methyl]-2,5-dimethylphenyl}-N-methylimidoformamide,

N'-[4-(3-chloro-4-methylbenzyl)-2,5-dimethylphenyl]-N-ethyl-N-methylimidoformamide,

N'-{2,5-dimethyl-4-[(1,1,3-trimethyl-2,3-dihydro-1H-inden-5-yl)methyl]phenyl}-N-ethyl-N-methylimidoformamide,

N'-{2,5-dimethyl-4-[(1,1,3-trimethyl-2,3-dihydro-1H-inden-5-yl)methyl]phenyl}-N-isopropyl-N-methylimidoformamide,

N'-{2,5-dimethyl-4-[(1,1,3-trimethyl-2,3-dihydro-1H-inden-5-yl)methyl]phenyl}-N-methyl-N-propylimidoformamide,

N'-[2,5-dimethyl-4-(5,6,7,8-tetrahydronaphthalen-2-ylmethyl)phenyl]-N-ethyl-N-methylimidoformamide,

N'-[2,5-dimethyl-4-(5,6,7,8-tetrahydronaphthalen-2-ylmethyl)phenyl]-N-isopropyl-N-methylimidoformamide,

N'-[2,5-dimethyl-4-(5,6,7,8-tetrahydronaphthalen-2-ylmethyl)phenyl]-N-methyl-N-propylimidoformamide,

2,5-dimethyl-N-[(1E)-piperidin-1-ylmethylene]-4-(5,6,7,8-tetra-hydronaphthalen-2-ylmethyl)aniline,

4-(4-tert-butyl-3-chlorobenzyl)-2,5-dimethyl-N-[(1E)-piperidin-1-ylmethylene]aniline,

N'-(4-{3-Chlor-4-[(trimethylsilyl)methyl]benzyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,

N'-[4-(3-chloro-4-isobutylbenzyl)-2,5-dimethylphenyl]-N-ethyl-N-methylimidoformamide,

N'-[4-(4-butyl-3-chlorobenzyl)-2,5-dimethylphenyl]-N-ethyl-N-methylimidoformamide,

N'-(2,5-dimethyl-4-{4-(trifluoromethyl)-3-[(trimethylsilyl)methyl]benzyl}phenyl)-N-ethyl-N-methylimidoformamide, and

N'-{4-[3-cyclophenyl-4-(trifluoromethyl)benzyl]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide.

This description of the 3,4-substituted benzylphenyl amidines compounds in US 8,080,688 is erroneous and unintended for the following reasons: i) Claim 4 implies that the Applicant intends to claim 3,4-substituted phenoxyphenyl amidines rather than 3,4-substituted bunylphenyl amidines; ii) 3,4-substituted bunzylphenyl amidines cannot be prepared using the procedures described in the Schemes and Examples; iii) Table IV on pages 48-49 of US 8080688 describes 3,4-substituted phenoxyphenyl amidines.

Therefore, given these typographical errors, which are reflected in US 8080688 and the corresponding EP application No. 2120558, the compounds of this invention are new.

The novelty/non-obviousness of the compounds of the present invention can be seen in the comparative results presented in the example section, where it is observed that the compounds of the present invention further increase the effectiveness of protecting crops from attack by pests, microorganisms, weeds or abiotic stress.

DETAILED DESCRIPTION OF THE INVENTION

This invention relates to compounds of formula (I)

Where

R ¹ is selected from the group containing hydrogen, CN, SR'', _S (O) _n R'', _OR '', C _1-12 alkyl, C _1-12 alkoxy, C _1-12 alkylthio, C 2-12 alkenyl, C 2-12 alkynyl, C _1-12 haloalkyl, C _2-12 haloalkenyl, C _2-12 haloalkyne yl, C _3-8 cycloalkyl, C _4-8 cycloalkenyl, C _5-8 cycloalkynyl; where in the system of cyclic rings, one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, and S(O)nN, O, and S(O) _n ;

R ² and R ³ are independently selected from the group containing hydrogen, CN, S(O) _n R'', OR', ₍ C=O)-R'', C _1-12 alkyl, C 2-12 alkenyl, C _2-12 alkynyl, C _1-12 haloalkyl, C _2-12 haloalkenyl, C _2-12 haloalkynyl, C _3-8 cycloalkyl, C _4-8 cycloalkenyl, C _5-8 cycloalkynyl, C _5-18 aryl, C _7-19 aralkyl, C _7-19 alkaryl; where in the system of cyclic rings one or more carbon atoms can be replaced by heteroatoms selected from the group containing N, O, and S(O) _n ; or

R ¹ and R ² , R ² and R ³ or R ¹ and R ³ together with the atoms to which they are attached, or together with subsequent atoms selected from the group containing C, N, O, S and optionally including 1-3 ring elements, selected from the group containing C(=O), C(=S), S(O) _m and SiR' ₂ , may form a ring with 4-7 elements, which may be partially substituted by one or more X, R' , OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR'₂; and where each R ¹ , R ² , and R ³ may optionally be substituted with one or more groups selected from the group consisting of X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR'₂;

R ⁴ , R ⁵ , R ⁶ и R ⁷ независимо выбраны из группы, содержащей водород, X, CN, SCN, SF ₅ , S(O) _n R'', SiR' ₃ , OR'', NR'R'', (C=O)-R'', CR'=NR'', С _1-12 -алкил, C _2-12 -алкенил, С _2-12 -алкинил, С _1-12 -галоалкил, С _2-12 -галоалкенил, С _2-12 -галоалкинил, С _1-12 -галоалкокси, C _1-12 -галоалкилтио, С _3-8 -циклоалкил, С _4-8 -циклоалкенил, С _5-8 -циклоалкинил, С _3-8 -циклоалкокси, С _5-8 -циклоалкилтио, С _5-18 -арил, С _7-19 -аралкил, С _7-19 -алкрил; where in the system of cyclic rings one or more carbon atoms can be replaced by heteroatoms selected from the group containing N, O, and S(O) _n ; and all groups above may be optionally substituted with one or more groups selected from the group consisting of X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR'₂; or

where, R ⁴ and R ⁷ or R ⁵ and R ⁶ together with the atoms to which they are attached, or together with subsequent atoms selected from the group containing C, N, O, S and optionally including 1-3 ring elements, selected from the group containing C(=O), C(=S), S(O) _m and SiR' ₂ , may form a ring with 4-7 elements, which may be partially substituted by one or more X, R', OR', SR ', NR' ₂ , SiR' ₃ , COOR', CN, and CONR'₂; and where each R ⁴ , R ⁵ , R ⁶ and R ⁷ may optionally be substituted with one or more groups selected from the group consisting of X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR'₂;

R ⁸ и R ⁹ независимо выбраны из группы, содержащей водород, X, CN, SCN, S(O) _n R'', OS(O) _n R'', SiR' ₃ , OSiR' ₃ , NR'R'', NR'S(O) _n R'', (C=O)-R'', CR'=NR'', C _1-12 -алкил, С _2-12 -алкенил, С _2-12 -алкинил, С _1-12 -алкокси, С _1-12 -галоалкил, С _2-12 -галоалкенил, С _2-12 -галоалкинил, С _1-12 -галоалкокси, С _1-12 -галоалкилтио, С _3-8 -циклоалкил, С _4-8 -циклоалкенил, С _5-8 -циклоалкинил, С _3-8 -циклоалкокси, С _3-8 -циклоалкилтио, С _5-18 -арил, С _7-19 -аралкил, С _7-19 -алкарил; where in the system of cyclic rings one or more carbon atoms can be replaced by heteroatoms selected from the group containing N, O, and S(O) _n ; and all groups above may be substituted with one or more groups selected from the group consisting of X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR'₂; or where

R ⁸ and R ⁹ together with the atoms to which they are attached, or together with subsequent atoms selected from the group containing C, N, O, S, and optionally including 1-3 ring elements selected from the group containing C(=O), C(=S), S(O) _m and SiR' ₂ , may form a ring with 4-7 elements, which may be partially substituted by one or more X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR'₂; or where

R ⁸ and R ⁹ together with the atoms to which they are attached may form the group ═C(R'R'''), ═S, ═NR''';

A is selected from the group containing fused or unfused C _6-18 -aryl, C _5-18 -heteroaryl, where one or more carbon atoms are replaced by heteroatoms selected from N, O, S, and optionally including 1-3 ring elements selected from the group containing C(=O), C(=S), S(O) _m and SiR' ₂ , optionally substituted with one or more R ¹⁰ groups; with the proviso that heteroaryl is not triazolyl or triadiazolyl; Where

R ¹⁰ выбран из группы, содержащей водород, X, CN, SCN, SF ₅ , R'', OR'', NO ₂ , NR'' ₂ , SiR' ₃ , (C=O)-R'', S(O) _n R'', OS(O) _n R'', NR'S(O) _n R'', OSiR' ₃ , С _1-8 -алкил-S(O) _n R'', C _1-8 -алкил-(С=O)-R'', CR'=NR'', S(O) _n C _5-18 -арил, S(O) _n C _7-19 -аралкил, S(O) _n C _7-19 -алкил, C _1-12 -алкил, С _2-12 -алкенил, С _2-12 -алкинил, C _1-12 -галоалкил, C _2-12 -галоалкенил, С _2-12 -галоалкинил, С _1-12 -алккси, C _1-12 -алкилтио, C _1-12 -галоалкокси, С _1-12 -галалкилтио, С _3-12 -цикоалкил, С _4-8 -циклоалкенил, С _5-8 -цикоалкинил, С _3-8 -циклоалкокси, С _3-8 -цикоалкилтио, С _7-19 -аралкил, С _7-19 -алкарил; bicyclic C _5-12 alk, C _7-12 alkenyl; where in the system of cyclic rings one or more carbon atoms can be replaced by heteroatoms selected from the group containing N, O, and S(O) _n ; and all groups above may be substituted with one or more groups selected from the group consisting of X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR'₂;

and where each R ⁸ , R ⁹ and R ¹⁰ may be optionally substituted with one or more groups selected from the group consisting of X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR'₂;

Where

X is halogen;

R' represents hydrogen, straight or branched chain C _1-12 alkyl or cyclic C _3-10 alkyl, which are optionally substituted with one or more X;

R'' represents hydrogen; NR' ₂ , OR', straight or branched chain C _1-12 -alkyl, C _1-12 -haloalkyl, cyclic C _3-8 -alkyl, which are optionally substituted by one or more groups selected from the group consisting of X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR' ₂ , C _5-18 -ar silt, which is optionally substituted by one or more R';

R''' is selected from the groups consisting of hydrogen, R'', CN, OR', (C=O)-R', COOR', CONR' ₂ straight or branched C _1-12 alkyl, C _2-12 alkenyl, C _2-12 alkynyl; cyclic C _3-8 alkyl, C _4-8 alkenyl, C _5-8 alkynyl; C _5-18 aryl, C _7-19 aralkyl, C _7-19 alkaryl; where in the system of cyclic rings one or more carbon atoms can be replaced by heteroatoms selected from the group containing N, O, and S(O) _n ; and all groups above may be substituted with one or more groups selected from the group consisting of X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR'₂; or

R' and R''', together with the atoms to which they are attached, or together with subsequent atoms selected from the group consisting of N, O, and S(O) _n , may form a ring with 3-6 elements, which may be partially substituted by one or more X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR'₂; Where,

m and n are integers, where n=0, 1 or 2; and m=1 or 2.

In accordance with other embodiments, the compounds of formula (Ia) can also be described as

Where

R ^x and R ^y are independently selected from the group consisting of hydrogen, hydroxy, CN, NO ₂ , COOR', S(O) _n R'', OR', (C=O)-R'', C ₁ -C ₁₂ alkyl, C 2-12 alkenyl, C _2-12 alkynyl, C _3-8 cycloalkyl, C _4-8 cycloalkenyl, C _5-8 cycloalkynyl, C _{5 -18} -aryl, C _7-19 -aralkyl, C _7-19 -alkaryl; where in the system of cyclic rings one or more carbon atoms can be replaced by heteroatoms selected from the group containing N, O, and S(O) _n ; or

R ^x and R ^y together with the atoms to which they are attached, or together with subsequent atoms selected from the group containing C, N, O, S and optionally including 1-3 ring elements selected from the group containing C(=O), C(=S), S(O) _m and SiR' ₂ , may form a ring with 3-7 elements, which may be partially substituted by one or more X, R', OR', SR', NR' ₂ , SiR ' ₂ , COOR', CN, and CONR'₂;

and where all groups R ^x and R ^y may be optionally substituted with one or more groups selected from the group consisting of X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR'₂;

and all other substitutions A and R ⁴ -R ¹⁰ are as defined in one of the above embodiments.

In another exemplary preferred substitution, R ¹ a compound of formula (I) is hydrogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 alkylthio, C _1-6 haloalkyl, C _3-8 cycloalkyl.

In another example of a more preferred substitution, the R ¹ compound of formula (I) is hydrogen, C _1-6 alkyl.

In another exemplary preferred substitution, R ² and R ³ a compound of formula (I) are C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _1-6 alkoxy, C _1-6 alkylthio, C _1-6 haloalkyl, C _3-8 cycloalkyl.

In another embodiment, R ¹ and R ² , R ² and R ³ or R ¹ and R ³ together with the atoms to which they are attached or together with subsequent atoms selected from the group containing C, N, O, S and optionally including 1-3 ring elements selected from the group containing C(=O), C(=S), S(O) _m and SiR' ₂ may form a ring with 4-7 elements, which may be partially substituted by one or more X, R', OR', SR' and CN.

In another embodiment, preferred ring formation structures with R ¹ and R ² , R ² and R ³ or R ¹ and R ³ substitutions together with the atoms to which they are attached are azetidine, pyrrolidine, imidazoline, oxazolidine, piperidine, morpholine, thiomorpholine, piperazine, 1-methyl piperazine, 1-methylpyrrolidine, 1-methylpiperidine, 3 -methyl-1,3-thiazinan.

In another embodiment, the preferred substitution, R ⁴ and R ⁵ compounds of General formula (I) are X, CN, S(O) _n R'', NR'R'', (C=O)-R'', CR'=NR'', C _1-6 -alkyl, C _2-6 -alkenyl, C 1-6 -haloalkyl, C _1-6 -alkoxy, C _1-6 -haloalkylthio, C _{3-8 -cyclo alkyl, C 3-8 -cycloalkylthio} .

In another embodiment, the preferred substitution, R ⁶ and R ⁷ compounds of General formula (I) are hydrogen, X, CN, S(O) _n R'', NR'R'', (C=O)-R'', CR'=NR'', C _1-6 -alkyl, C _2-6 -alkenyl, C 1-6 -haloalkyl, C _1-6 -alkoxy, C _1-6 -haloalkylthio, C _{3- 8} -cycloalkyl, C _3-8 -cycloalkylthio.

R ⁴ and R ⁷ or R ⁵ and R ⁶ together with the atoms to which they are attached, or together with subsequent atoms selected from the group containing C, N, O, S and optionally including 1-3 ring elements, selected from the group containing C(=O), C(=S), S(O) _m and SiR' ₂ may form a ring with 4-7 elements, which may be partially replaced by one or more X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR'₂; and where each R ⁴ , R ⁵ , R ⁶ and R ⁷ may optionally be substituted with one or more groups selected from the group consisting of X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR'₂;

In another preferred substitution, R ⁸ and R ⁹ compound of formula (I) are X, CN, S(O) _n R'', NR'R'', (C=O)-R'', CR'=NR'', C _1-6 alkyl, C _{1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy} , C _1-4 alkylthio, C _1-6 halo alkylthio, C _3-8 cycloalkyl, _{C 3-8 cycloalkoxy} , C _3-8 cycloalkylthio.

In another embodiment, R ⁸ and R ⁹ together with the atoms to which they are attached, or together with subsequent atoms selected from the group containing C, N, O, S, may form a ring with 3-6 elements, which may be partially substituted with one or more X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR' ₂ .

In another embodiment, the preferred substitution R¹⁰ in the compound of formula (I) are hydrogen X, CN, SCN, SF₅, R'', OR'', NO₂,NR''₂, SiR'₃, (C=O)-R'', S(O)_nR'', C_1-8-alkyl-S(O)_nR'', C_1-6-alkyl-(C=O)-R'', CR'=NR'', C_2-6-alkenyl, C_2-6-alkynyl, C_1-6-haloalkyl, C_2-6-haloalkenyl, C_1-12-alkoxy, C_1-12-alkylthio, C_1-12-haloalkoxy, C_1-12-haloalkylthio, C_3-8-cycloalkyl, C_4-8-cycloalkenyl, C_3-8-cycloalkoxy, C_3-8-cycloalkylthio.

In another embodiment, two R ¹⁰ together with the atoms to which they are attached, or together with subsequent atoms selected from the group containing C, N, O, S and optionally including 1-3 ring elements selected from the group containing of C(=O), C(=S), S(O) _m and SiR' ₂ , may form a ring with 4-10 elements, which may be partially substituted by one or more X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR' ₂ .

In another embodiment, preferred A is phenyl, naphthalenyl, furyl, trienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, imidazolyl, oxadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothio phenyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinazolinyl, cinnonyl; substituted with one or more R ¹⁰ .

In another embodiment, preferred A is phenyl, naphthalene, thienyl, isothiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl; substituted with one or more R ¹⁰ .

In another embodiment, where each R ¹ -R ¹⁰ may be optionally substituted with one or more groups selected from the group consisting of X, R'', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR'₂;

In another embodiment, the preferred compound of formula (I) are

N'-(4-benzyl-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(4-(methoxy(phenyl)methyl)-2,5-dimethylphenyl)-N-methylformimidamide;

N'-(4-(3,5-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(4-bromobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3,4-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dimethyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(4-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dimethyl-4-(4-(methylthio)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dimethyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2-bromo-4-(4-bromobenzyl)-3,6-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3-chlorobegoyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dimethyl-4-(4-(methylsulfonyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3-bromobenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3-bromobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(4-(2-fluorobegoyl)-2,5-dimethylphenyl)-N-methylformimidamide;

N'-(2-chloro-4-(2-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(2-chlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dimethyl-4-(4-(methylsulfonyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(3,4-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(3,5-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(4-bromobenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dimethyl-4-(2-(methylthio)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dimethyl-4-(2-(methylsulfonyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dimethyl-4-(2-(methylsulfonyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(2,5-dimethylbenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3-chloro-4-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(4-(3-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;

N'-(2-chloro-4-(3-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dimethyl-4-((Z)-(methylimino)(phenyl)methyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dimethyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dimethyl-4-(2-phenyl-1,3-dithiolan-2-yl)phenyl)-N-ethyl-N-methylformimidamide;

N-(4-(3-chloro-4-fluorobenzyl)-2,5-dimethylphenyl)-1-morpholinomethanimine;

N-(4-(3-chloro-4-fluorobenzyl)-2,5-dimethylphenyl)-1-(piperidin-1-yl)methanamine;

N-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-1-morpholinomethanimine;

N-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-1-(piperidin-1-yl)methanamine;

N-(2-chloro-4-(3-fluorobenzyl)-5-methylphenyl)-1-morpholinomethanimine;

N-(2-chloro-4-(3-fluorobenzyl)-5-methylphenyl)-1-(piperidin-1-yl)methanamine;

N-(2-chloro-4-(2-fluorobenzyl)-5-methylphenyl)-1-morpholinomethanimine;

N'-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;

N'-(2-chloro-4-(3-fluorobenzyl)-5-methylphenyl)-N-methylformimidamide;

N'-(2-chloro-5-methyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-5-methyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(4-(3-methoxybenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;

N'-(2,5-dimethyl-4-(3-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3-cyanobegoyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(4-cyanobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dimethyl-4-(3-nitrobenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dimethyl-4-(2-nitrobenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dimethyl-4-(3-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(4-(3-fluoro-5-(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-methylformimidamide;

N'-(2,5-dimethyl-4-(2-methyl-5-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(4-(4-methoxybenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;

N-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-1-morpholinomethanimine;

N-(4-(4-fluorobenzyl)-2,5-dimethylphenyl)-1-morpholinomethanimine;

N-ethyl-N'-(4-(4-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;

N-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-1-(piperidin-1-yl)methanamine;

N-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-1-(piperidin-1-yl)methanamine;

N-(4-(4-fluorobenzyl)-2,5-dimethylphenyl)-1-(piperidin-1-yl)methanamine;

N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-methoxy-N-methylformimidamide

N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-methoxy-N-methylformimidamide

N-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-1-morpholinomethanimine;

N-cyano-N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)formimidamide;

N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-cyanoformimidamide;

N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-isopropylformimidamide;

N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-isopropylformimidamide;

N'-(2-chloro-4-(4-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(4-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(3-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-5-methyl-4-(3-nitrobenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(3-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(difluoro(phenyl)methyl)-2-iodo-3,6-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-benzyl-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-5-methyl-4-(2-nitrobenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(4-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-5-methyl-4-(4-((trifluoromethyl)thio)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(3-chlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(4-chlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-5-methyl-4-(3-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-isopropyl-N-methylformimidamide;

N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-isopropyl-N-methylformimidamide;

N-allyl-N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;

N-allyl-N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;

N-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-1-thiomorpholinomethanimine;

N-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-1-thiomorpholinomethanimine;

N-(cyclopropylmethyl)-N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;

N-(cyclopropylmethyl)-N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-isopropylformimidamide;

N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-(cyclopropylmethyl)-N-isopropylformimidamide;

N'-(4-(2-cyclobenzyl)-2,5-dimethylphenyl)-N-cyano-N-(cyanomethyl)formimidamide;

N-cyano-N-(cyanomethyl)-N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)formimidamide;

N'-(2,5-dimethyl-4-(4-((trifluoromethyl)thio)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dimethyl-4-(2-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dimethyl-4-(4-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(4-chloro-3-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3,5-bis(trifluoromethyl)benzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dimethyl-4-(4-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dimethyl-4-(4-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(2-chloro-4-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(2-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-5-methyl-4-(4-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-5-methyl-4-(2-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-5-methyl-4-(2-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dimethyl-4-(4-methyl-3-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(4-chloro-3-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3,5-bis(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3-(1-cycloethyl)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(4-chloro-3-methylbenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(4-(4-fluoro-3-methylbenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;

N'-(4-(2-chloro-4-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3-(dimethiamino)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(2,3-dimethylbenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3,4-dimethylbenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3,5-dimethylbenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(2-cyanobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dimethyl-4-(2-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dimethyl-4-(4-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3-chloro-2-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(4-fluoro-3-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(4-chloro-3-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

(E)-N'-(2-chloro-5-methyl-4-(4-(tritormethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-5-methyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(3-chloro-2-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-5-methyl-4-(3-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(2-chloro-3-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(3-chloro-2-fluoro-5-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(cyano(phenyl)methyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(2,3-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(3,5-difluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(3,5-dimethylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(2-chloro-3-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3,5-difluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(2,3-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3-chloro-2-fluoro-5-(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3-chloro-5-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(4-chloro-3-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(3-fluoro-4-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(3,4-difluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(3-fluoro-4-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(3-fluoro-5-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dichloro-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(4-chloro-3-(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(2-chloro-5-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(4-(3-fluoro-4-methylbenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;

N'-(4-(4-chloro-3-(trifluoromethoxy)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3,4-difluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dichloro-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dichloro-4-(3-fluorobenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dichloro-4-(2-fluorobenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dichloro-4-(2-chlorobenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dichloro-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dichloro-4-(3-chlorobenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(2,6-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(2-bromobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(2-chloro-6fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(4-(3-fluoro-5-methoxybenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;

N-ethyl-N'-(4-(5-fluoro-2-methylbenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;

N-ethyl-N'-(4-(3-fluoro-4-(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-methylformimidamide;

N'-(4-(2-chloro-5-(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(2,5-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(2,4-difluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(2,4-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(4-(2-fluorobenzyl)phenyl)-N-methylformimidamide;

N'-(4-(2-chlorobenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(5-fluoro-2-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(2,5-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(4-fluoro-2-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(2-chloro-5-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(3-fluoro-5-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(2,3-dimethylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(5-fluoro-2-methyl-4-(3-methylbenzyl)phenyl)-N-methylformimidamide;

N-ethyl-N'-(5-fluoro-4-(3-fluorobenzyl)-2-methylphenyl)-N-methylformimidamide;

N'-(4-(3-chlorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(2-chlorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(5-fluoro-2-methyl-4-(4-methylbenzyl)phenyl)-N-methylformimidamide;

N'-(2-chloro-4-(3-chloro-5-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(4-chloro-3-(trifluoromethoxy)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(2-chloro-5-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(2,4-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(2,4-difluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(4-fluoro-3-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dichloro-4-(3-(tritormethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-dichloro-4-(3-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(2-chloro-6-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(5-fluoro-4-(2-fluorobenzyl)-2-methylphenyl)-N-methylformimidamide;

N-ethyl-N'-(5-fluoro-2-methyl-4-(2-methylbenzyl)phenyl)-N-methylformimidamide;

N'-(2-chloro-4-(cyano(4-(trifluoromethyl)phenyl)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(cyano(3-(trifluoromethyl)phenyl)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(cyano(4-fluorophenyl)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-((3-chloro-4-fluorophenyl)(cyano)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(cyano(p-tolyl)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-((2-chlorophenyl)(cyano)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-((4-chlorophenyl)(cyano)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(cyano(3-fluorophenyl)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(2,6-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(5-fluoro-2-methyl-4-(3-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide;

N'-(2-cyclopropyl-4-(3-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-cyclopropyl-5-methyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3-chlorobenzyl)-2-cyclopropyl-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(4-(3-fluoro-5-methylbenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;

N-ethyl-N'-(4-(2-fluoro-4-(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-methylformimidamide;

N'-(2,5-dimethyl-4-(pyridin-2-ylmethyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-4-(2,6-difluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-chloro-5-methyl-4-(pyridin-3-ylmethyl)phenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(2-fluoro-5-methyl-4-(3-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide;

N-ethyl-N'-(2-fluoro-5-methyl-4-(3-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide;

N-ethyl-N'-(2-fluoro-5-methyl-4-(2-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide;

N'-(4-(3-chlorobenzyl)-2-fluoro-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(2-fluoro-4-(3-fluorobenzyl)-5-methylphenyl)-N-methylformimidamide;

N-ethyl-N'-(2-fluoro-5-methyl-4-(3-methylbenzyl)phenyl)-N-methylformimidamide;

N-ethyl-N'-(2-fluoro-5-methyl-4-(4-methylbenzyl)phenyl)-N-methylformimidamide;

N-ethyl-N'-(2-fluoro-5-methyl-4-(2-methylbenzyl)phenyl)-N-methylformimidamide;

N'-(4-(2-chlorobenzyl)-2-fluoro-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(2-fluoro-4-(2-fluorobenzyl)-5-methylphenyl)-N-methylformimidamide;

N'-(2,5-dimethyl-4-((Z)-(methylimino)(o-tolyl)methyl)phenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(4-(3-fluorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-methylformimidamide;

methyl N-(2-bromo-4-(4-bromobenzyl)-3,6-dimethyl phenyl)formimidate

N'-(4-(3-chlorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2-bromo-3,6-dimethyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N-(2-chloro-4-(2-fluoro-6-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-cyclopropyl-4-(2-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-cyclopropyl-5-methyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(2-chlorobenzyl)-2-cyclopropyl-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-cyclopropyl-5-methyl-4-(3-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(2-fluoro-4-(4-methylbenzyl)-5-(trifluoromethyl)phenyl)-N-methylformimidamide;

N'-(4-(2-cyclobenzyl)-2-fluoro-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(2-fluoro-4-(2-fluorobenzyl)-5-(trifluoromethyl)phenyl)-N-methylformimidamide;

N-ethyl-N'-(2-fluoro-4-(2-methylbenzyl)-5-(trifluoromethyl)phenyl)-N'-methylformimidamide;

N'-(4-(3-cyclobenzyl)-2-fluoro-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(2-fluoro-4-(3-fluorobenzyl)-5-(trifluoromethyl)phenyl)-N-methylformimidamide;

N-ethyl-N'-(2-fluoro-4-(3-methylbenzyl)-5-(trifluoromethyl)phenyl)-N-methylformimidamide;

N-ethyl-N'-(2-fluoro-5-(trifluoromethyl)-4-(3-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide;

N-ethyl-N'-(2-fluoro-4-(3-(trifluoromethoxy)benzyl)-5-(trifluoromethyl)phenyl)-N-methylformimidamide;

N-ethyl-N-methyl-N'-(5-methyl-4-(2-methylbenzyl)-2-(methylsulfonyl)phenyl)formimidamide;

N-ethyl-N-methyl-N'-(5-methyl-4-(4-methylbenzyl)-2-(methylsulfonyl)phenyl)formimidamide;

N'-(5-chloro-4-(cyano(5-fluoro-2-methylphenyl)methyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;

methyl 2-(2-chloro-4-(((ethyl(methyl)amino)methylene)amino)-5-methylphenyl)-2-(3-chlorophenyl)acetate

N'-(4-(1-(4-bromophenyl)vinyl)-5-chloro-2-methylphenyl)-N-ethyl-N-methylformimidamide;

2-(2-chloro-4-(((ethyl(methyl)amino)methylene)amino)-5-methylphenyl)-2-(3-fluorophenyl)-N,N-dimethylpropanamide;

2-(2-chloro-4-(((ethyl(methyl)amino)methylene)amino)-5-methylphenyl)-2-(5-fluoro-2-methylphenyl)-N,N-dimethylacetamide;

N'-(5-chloro-4-((4-chloro-3-fluorophenyl)(cyano)methyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-difluoro-4-(2-fluorobenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3-chlorobenzyl)-2,5-difluorophenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-difluoro-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-difluoro-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(2-chlorobenzyl)-5-cyano-2-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(5-cyano-4-(2-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(5-cyano-2-methyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3-chlorobenzyl)-5-cyano-2-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(5-cyano-4-(3-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(5-cyano-2-methyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(5-cyano-2-methyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(2-chlorobenzyl)-2,5-difluorophenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-difluoro-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(5-chloro-4-(2-chlorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(5-chloro-4-(2-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(5-chloro-2-methyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(5-chloro-4-(3-chlorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(5-chloro-4-(3-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;

N'-(5-chloro-2-methyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(5-chloro-2-methyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(2-chlorobenzyl)-2-cyclopropyl-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2-cyclopropyl-4-(3-methylbenzyl)-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2-cyclopropyl-4-(4-methylbenzyl)-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(3-chlorobenzyl)-2-cyclopropyl-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2-cyclopropyl-4-(3-fluorobenzyl)-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide;

N-(2-cyclopropyl-4-(4-uyclopropylbenzyl)-3,6-dimethylphenyl)-N-ethyl-N-methylformimidamide;

N'-(2-cyclopropyl-4-(2-methylbenzyl)-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(2,5-difluoro-4-(3-fluorobenzyl)phenyl)-N-ethyl-N-methylformimidamide;

N'-(4-(2-chlorobenzyl)naphthalen-1-yl)-N-ethyl-N-methylformimidamide;

N-ethyl-N-methyl-N'-(4-(2-methylbenzyl)naphthalen-1-yl)formimidamide;

N'-(2-chloro-4-(cyano(3-(trifluoromethyl)phenyl)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N-methyl-N'-(5-methyl-4-(3-methylbenzyl)-2-(methylsulfonyl)phenyl)formimidamide;

N-ethyl-N'-(4-(2-fluorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-1N-methylformimidamide;

N'-(4-(2-chlorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N-methyl-N'-(5-methyl-2-(methylsulfonyl)-4-(3-(trifluoromethyl)benzyl)phenyl)formimidamide;

N-ethyl-N-methyl-N'-(5-methyl-2-(methylsulfonyl)-4-(3-(trifluoromethoxy)benzyl)phenyl)formimidamide;

N'-ethyl-N-methyl-N'-(5-methyl-4-(2-methylbenzyl)-2-(methylsulfonyl)phenyl)formimidamide;

N-ethyl-N-methyl-N'-(5-methyl-4-(4-methylbenzyl)-2-(methylsulfonyl)phenyl)formimidamide;

N-(4-(3-chlorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N'-(4-(3-fluorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-methylformimidamide;

N-ethyl-N-methyl-N'-(5-methyl-4-(3-methylbenzyl)-2-(methylsulfonyl)phenyl)formimidamide;

N-ethyl-N'-(4-(2-fluorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-methylformimidamide;

N'-(4-(2-chlorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-ethyl-N-methylformimidamide;

N-ethyl-N-methyl-N'-(5-methyl-2-(methylsulfonyl)-4-(3-(trifluoromethyl)benzyl)phenyl)formimidamide;

N-ethyl-N-methyl-N'-(5-methyl-2-(methylsulfonyl)-4-(3-(trifluoromethoxy)benzyl)phenyl)formimidamide and

N-ethyl-N'-(5-fluoro-2-methyl-4-(3-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide.

* Compound names generated using Chemdraw Professional16.0

According to the invention, any compound may exist in one or more optical, geometric, or chiral isomeric forms, depending on the number of asymmetric centers in the compound. Therefore, the invention applies equally to all optical isomers and their racemic and scalemic mixtures (the term "scalemic" means a mixture of enantiomers in different proportions) and mixtures of all possible stereoisomers in all proportions. Diastereoisomers and/or optical isomers may be separated according to methods known per se to those skilled in the art.

According to the invention, any compounds may also exist in one or more geometric isomeric forms, depending on the number of double bonds in the compound. The invention therefore applies equally to all geometric isomers and to all possible mixtures in all proportions. The geometric isomers may be separated according to general methods known per se to those skilled in the art.

According to the invention, any compounds may also exist in one or more amorphous or isomorphic or polymorphic forms, depending on their preparation, purification, storage, and various other factors. Therefore, the invention relates to all possible amorphous, isomorphic and polymorphic forms in all proportions. Amorphous, isomorphic and polymorphic forms may be prepared and/or separated and/or purified in accordance with general methods known per se to those skilled in the art.

In the above description, the term "alkyl", whether used alone or in a compound word such as "alkylthio" or "haloalkyl", includes straight or branched alkyl, such as methyl, ethyl, p-propyl, i-propyl, or various isomers of butyl, pentyl, or hexyl.

"Alkenyl" includes straight or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl and various isomers of butenyl, pentenyl and hexenyl. "Alkenyl" also includes polyenes such as 1-propadienyl and 2,4-hexadienyl.

"Alkynyl" includes straight or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the various isomers of butynyl, pentynyl and hexynyl. "Alkynyl" also includes fragments of the molecule consisting of different triple bonds, such as 2,5-hexadiynyl.

"Cyclic alkyl" or "cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Cyclic alkenyl includes, for example, cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl. Similarly, cyclic alkynyl refers to cyclic pentynyl, hexynyl, heptynyl, and octynyl.

The term "aryl" is used to refer to a group that contains an aromatic carbon group, including, but not limited to, phenyl, naphthalene, biphenyl, anthracene, and the like. The aryl group may be substituted or unsubstituted. In addition, the aryl group may be a single ring structure or be composed of multiple ring structures, which may be fused ring structures or attached through one or more overlapping groups, such as a carbon-carbon bond.

The term "hetero" when used with rings means a ring in which at least one ring atom is not carbon and which may contain 1-4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each ring contains no more than 4 nitrogen atoms, no more than 2 oxygen atoms and no more than 2 sulfur atoms.

The term "heterocyclyl" means a cyclic ring system in which at least one ring atom is not carbon and which contains heteroatoms independently selected from the group consisting of nitrogen, oxygen, sulfur, phosphorus, boron, etc.

The term "heterocyclyl" can also be classified as "non-aromatic heterocyl" and "aromatic heterocyl or heteroaryl".

The term "non-aromatic heterocyl" includes a fused or non-fused three to fifteen component, preferably three to twelve component saturated or fully or partially unsaturated heterocycle, monocycle or polycycle (spiro, fused, combined, non-fused) heterocycle wherein the heteroatom is selected from the group of oxygen, nitrogen and sulfur; and if the ring contains more than one oxygen atom, they are not adjacent; non-limiting examples of non-aromatic heterocyls include oxetanyl, oxiranil; aziridinyl; triiranil; azetidinyl, thiethanil, dithiethanil, diazetidinyl, 2-tetrahydrofuranyl; 3-tetrahydrofuranyl; 2-tetrahydrothienyl; 3-tetrahydrothienyl; 2-pyrrolidinyl; 3-pyrrolidinyl; 3-isoxazolidinyl; 4-isoxazolidinyl; 5-isoxazolidinyl; 3-isothiazolidinyl; 4-isothiazolidinyl; 2-tetrahydropyranyl; 4-tetrahydropyranyl. This definition also refers to heterocyclyl as part of a complex substituent, eg, heterocyclylalkyl (heterocyl radicals including the alkyl moiety as defined above), etc., unless otherwise specified.

The term "heteroaryl aryl" is used to denote a group that contains fused or unfused three to fifteen component, preferably three to twelve component, more preferably 5 or 6 component monocyclic or polycyclic unsaturated ring systems which contain heteroatoms selected from the group of oxygen, nitrogen, sulfur, phosphorus, boron, etc.

Non-limiting examples of 5-component heteroaryl groups include 2-furyl; 3-furyl; 2-thienyl; 3-thienyl; 2-pyrrolyl; 3-pyrrolyl; 3-isoxazolyl; 4-isoxazolyl; 5-isoxazolyl; 3-isothiazolyl; 4-isothiazolyl; 5-isothiazolyl; 3-pyrazolyl; 4-pyrazolyl; 5-pyrazolyl; 2-oxazolyl; 4-oxazolyl; 5-oxazolyl; 2-thiazolyl; 4-thiazolyl; 5-thiazolyl; 2-imidazolyl; 4-imidazolyl; 1,2,4-oxadiazol-3-yl; 1,2,4-oxadiazol-5-yl; 1,2,4-thiadiazol-3-yl; 1,2,4-thiadiazol-5-yl; 1,2,4-triazol-3-yl; 1,3,4-oxadiazol-2-yl; 1,3,4-thiadiazol-2-yl and 1,3,4-triazol-2-yl; 1-pyrrolyl; 1-pyrazolyl; 1,2,4-triazol-1-yl; 1-imidazolyl; 1,2,3-triazol-1-yl; 1,3,4-triazol-1-yl and similar substances.

Non-limiting examples of 6-component heteroaryl groups include 2-pyridinyl; 3-pyridinyl; 4-pyridinyl; 3-pyridazinyl; 4-pyridazinyl; 2-pyrimidinyl; 4-pyrimidinyl; 5-pyrimidinyl; 2-pyrazinyl; 1,3,5-triazin-2-yl; 1,2,4-triazin-3-yl; 1,2,4,5-tetrazin-3-yl and similar substances.

Non-limiting examples of benzofused 5-component heteroaryls include indol-1-yl; indol-2-yl; indol-3-yl; indol-4-yl; indol-5-yl; indol-6-yl; indol-7-yl; benzimidazol-1-yl; benzimidazol-2-yl; benzimidazol-4-yl; benzimidazol-5-yl; indazol-1-yl; indazol-3-yl; indazol-4-yl; indazol-5-yl; indazol-6-yl; indazol-7-yl; indazol-2-yl; 1-benzofuran-2-yl; 1-benzofuran-3-yl; 1-benzofuran-4-yl; 1-benzofuran-5-yl; 1-benzofuran-6-yl; 1-benzofuran-7-yl; 1-benzothiophen-2-yl; 1-benzothiophen-3-yl; 1-benzothiophen-4-yl; 1-benzothiophen-5-yl; 1-benzothiophen-6-yl; 1-benzothiophen-7-yl; 1,3-benzothiazol-2-yl; 1,3-benzothiazol-4-yl; 1,3-benzothiazol-5-yl; ,3-benzothiazol-6-yl; 1,3-benzothiazol-7-yl; 1,3-benzoxazol-2-yl; 1,3-benzoxazol-4-yl; 1,3-benzoxazol-5-yl; 1,3-benzoxazol-6-yl; 1,3-benzoxazol-7-yl and similar substances.

Non-limiting examples of benzo-fused 6-component heteroaryls include quinolin-2-yl; quinolin-3-yl; quinolin-4-yl; quinolin-5-yl; quinolin-6-yl; quinolin-7-yl; quinolin-8-yl; isoquinolin-1-yl; isoquinolin-3-yl; isoquinolin-4-yl; isoquinolin-5-yl; isoquinolin-6-yl; isoquinolin-7-yl; isoquinolin-8-yl and similar substances.

The term "aralkyl" denotes aryl hydrocarbon radicals, including the alkyl moiety as defined above. Examples include benzyl, phenylethyl and 6-naptylhexyl. As used herein, the term "aralkenyl" refers to any aryl hydrocarbon radicals, including the alkenyl moiety as defined above and the aryl moiety as defined above. Examples include styryl, 3-(benzyl)prop-2-enyl and 6-naptylhex-2-enyl.

The term "alkaryl" refers to an aryl group that contains an alkyl group; as used herein, the term "alkaryl" includes substituted and unsubstituted groups. One example of an alkaryl group is the 4-methylphenyl radical.

"Alkoxy" includes, for example, methoxy, ethoxy, n-pryloxy, isopropyloxy, and the various betoxy, pentoxy, and hexyloxy isomers.

"Alkylthio" includes the branched and unbranched flags of the atkylthio molecule, such as methylthio, ethylthio and the various propylthio, butylthio, pentylthio and hexylthio isomers.

The term "halogen", whether used alone or in a compound word such as "haloalkyl", includes fluorine, chlorine, bromine, and iodine.

The total number of carbon atoms in the substituent group is indicated by the prefix "C _ij ", where i and j are numbers from 1 to 21. For example, C _1-3 alkoxy means methoxy to propoxy. In the enumeration above, when a compound of formula (I) consists of one or more heterocyclic rings, all substituents are attached to such rings through any available carbon or nitrogen atoms, replacing the hydrogen on said carbon or nitrogen.

When a compound is substituted with a substituent with an index that indicates that the number of said substituents may exceed 1, said substituents (when greater than 1) are independently selected from the group of specified substituents. When the index indicates a range, for example, (R) _i+j, the number of substituents may be selected from integers i to j inclusive.

When a group contains a substituent, which may be hydrogen, for example R ¹ or R ² if the substituent is hydrogen, this equates to an unsubstituted specified group.

The invention also relates to compositions for the control of unwanted microorganisms, consisting of at least one compound of formula (I) and one or more inert carriers. The inert carrier may consist of agricultural aids, solutions, surfactant solvents and/or diluents.

The invention also relates to compositions for the control of unwanted microorganisms, consisting of at least one compound of formula (I) and/or one or more active compatible compounds selected from fungicides, bactericides, acaricides, insecticides, nematicides, herbicides, biopesticides, plant growth regulators, antibiotics, fertilizers and/or mixtures thereof.

The invention also relates to a composition in which the concentration of compounds of formula (I) varies from 1 to 90% by weight relative to the total weight of the composition, preferably from 5 to 50% by weight relative to the total weight of the composition.

The invention also relates to a method for controlling unwanted microorganisms, where the compounds of formula (I) are used for microorganisms and/or their natural environment.

The invention also provides a method for protecting seeds from undesirable microorganisms by using seeds treated with at least one compound of formula (I).

The compounds of formula (I) can be highly microbicidal and can be used to control undesirable microorganisms such as fungi, insects, mice, nematodes and bacteria, to protect crops and horticultural crops and to protect such materials.

The compounds of formula (I) may exhibit very good fungicidal properties and may be used for crop protection, for example to control Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

The compounds of formula (I) can be used as nematicides for crop protection, for example to control Rhabditida, Dorylaimida, and Tryplonchida.

The compounds of formula (I) can be used as crop protection insecticides, for example to control Lepidoptera, Coleoptera, Hemiptera, Homoptera, Thysanoptera, Diptera, Orthoptera and Isoptera.

The compounds of formula (I) can be used as acaricides for crop protection, for example to control Eriophyoidea, Tetranychoidea, Eupodoidea and Tarsonemidae.

The compounds of formula (I) can be used as bactericides for crop protection, for example to control Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

The compounds of formula (I) can be used as herbicides and can be effective against a wide range of economically important mono- and dicotyledonous pests. Monocotyledonous deciduous weed species may include Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria and Cyperus spp. from the annual group and perennial Agropyron, Cynodon, Imperata and Sorghum spp. and perennial Cyperus spp. Dicotyledonous deciduous weed species may include Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Sida, Matricaria and Abutilon species from the annual group, as well as Convolvulus, Cirsium, Rumex and Artemisia perennial deciduous weeds. Harmful plants that occur in rice such as Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus can be controlled with the compounds of formula (I).

The compounds of formula (I) can be used for radical or protective control of phytopathogenic fungi. Therefore, the invention relates to radical and protective methods for the control of phytopathogenic fungi using innovative active ingredients or compositions that are applied to seeds, plants and plant parts, fruits or soil in which the plant grows.

The compounds of formula (I) can be used to control or prevent phytopathogenic fungi, bacteria, insects, nematodes, crop or horticultural mice.

The compounds of formula (I) can be used to protect crops where the crops are cereals, wheat, rice, soybeans and other leguminous plants, fruits and fruit trees, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbits, oil plants, tobacco, coffee, tea, cocoa, sugar beets, sugar cane, cotton, potatoes, tomatoes, onions, peppers and other vegetables and ornamental plants.

According to the invention, as defined above, the carrier is a natural or synthetic, organic or inorganic substance with which the active ingredients are mixed or combined for better applicability, in particular for use on plants, plant parts or seeds. The carrier, which may be in solid or liquid form, is generally inert and should be suitable for agricultural use.

Useful solid carriers include, for example, ammonium salts and ground natural rocks, such as kaolins, clay, talc, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic rocks, such as finely ground silicate, aluminum oxides and silicates; useful solid carriers for granules include: for example, crushed or fractionated natural rocks, such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic flour, and granules of organic materials such as paper, sawdust, coconut husks, maize and tobacco stalks; useful emulsifiers and/or foaming agents, including: for example, non-ionic and aionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol esters, for example, alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, as well as protein hydrolysates; suitable dispersants are non-ionic and/or ionic substances, for example from the class of alcohols -POE and/or -POP esters, acids and/or POP POE esters, alkylaryl and/or POP POE ethers, fats and/or POP POE adducts, POE and/or POP polyol derivatives, POE and/or POP sorbitan or -sugar adducts, alkyl or aryl sulfates, alkyl- or arylsulfonates and alkyl or aryl phosphates or the corresponding PO ether adducts. Further suitable are oligo- or polymers, for example derived from vinyl monomers, from acrylic acid, from EO and/or PO alone or in combination with, for example, (poly) alcohols or (poly) amines. It is also possible to use lignin and its sulfonic acid derivatives, unmodified and modified celluloses, aromatic and/or aliphatic sulfonic acids, as well as formaldehyde adducts.

The active ingredients can be used as is or after being converted into traditional formulations, or in the form of their formulations, or use prepared forms, such as ready-to-use solutions, emulsions, aqueous and oily suspensions, powders, soakable powders, pastes, soluble powders, soluble tablets, dusts, soluble granules, granules for inoculation and suspoemulsion concentrations, natural products saturated with the active ingredient, synthetic substances saturated with the active ingredient, fertilizers , as well as microencapsulation into polymeric substances. The application is carried out in the traditional way, for example, by watering, spraying, fine spraying, using in incubators, spreading over the field, pollinating, aerating, applying and others. It is also possible to use the active ingredients in an ultra-low volume method, or to introduce a solution of the active ingredient or the active ingredient itself into the soil. Plant seeds can also be processed.

Also, active ingredients can be nanoformulated to further improve water solubility, thermal stability, bioavailability, sensory characteristics, and physiological performance.

Moreover, the choice of formulation type will depend on the particular use.

Said formulations can be prepared as such, for example by mixing the active ingredients with at least one conventional excipient, solution or solvent, emulsifier, dispersant and/or binder or fixative, wetting agent, water repellant, if necessary, drying agents and UV stabilizers, and if necessary, dyes and pigments, defoamers, preservatives, secondary thickeners, adhesives, gibberellins, as well as other technological auxiliary substances.

The invention includes not only formulations that are ready for use and can be applied with appropriate apparatus to plants or seeds, but also commercial concentrates that must be diluted with water before use.

The adjuvants used may include substances which are suitable for imparting certain properties to the composition itself and/or solutions derived from it (e.g. spray liquids, seed disinfection), such as certain technical properties and/or also certain biological properties. Typical adjuvants are fillers, solutions and carriers.

Suitable excipients are, for example, water, polar and non-polar organic chemical liquids, for example, from the aromatic and non-aromatic hydrocarbon classes (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may optionally also be substituted, esterified and/or esterified), ketones (such as acetone, cyclohexanone), ethers (including fats and oils), and (poly) ethers, unsubstituted and substituted amines, amides, lactams (such as N-alkylpyrrodidones) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide).

Liquefied gaseous excipients or carriers mean liquids which are in a gaseous state at standard temperature and at standard pressure, such as aerosol propellants such as halocarbons or butane, propane, nitrogen and carbon dioxide.

Tackifiers such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latex, such as arabia gum, polyvinyl alcohol and polyvinyl acetate, or other natural phospholipids such as cephalins and lecithins, and synthetic phospholipids can be used in the formulation. Also auxiliary substances can be mineral, vegetable oils and methyl vegetable oils.

If water is used as filler, it is also possible to use, for example, organic solvents as co-solvents. Useful liquid solvents are: aromatic compounds such as xylene, toluene or alkylnaphthalenes, chloride aromatic compounds or chloride aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, such as petroleum fractions, alcohols, such as butanol or glycol and their ethers and esters, ketones, such as , acetone, methyl ethyl ketone, methyl isobutyl ketone or cylohexanones, strong polar solvents such as dimethylformamide and dimethyl sulfoxide, or other water.

Compositions consisting of compounds of formula (I) may additionally include other components, such as surfactants. Suitable surfactants are emulsifiers and/or foaming agents, dispersants or wetting agents with ionic or non-ionic properties, or mixtures of such surfactants. Examples are salts of polyacrylic acid, salts of ignosulfonic acid, salts of phenosulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide with fatty alcohols or fatty acids or fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic esters, taurine derivatives (preferably alkyl taurates), polyethoxylated phosphoric acid esters. alcohols or phenols, fatty esters of polyols and derivatives of compounds containing sulfates, sulfonates and phosphonates, such as alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignosulphite waste solutions and methylcellulose. The presence of a surfactant is necessary if one of the active ingredients and/or one of the inert carriers is insoluble in water and exposed to water during application. The proportion of surfactants is 5-40% by weight of the invented composition.

Dyes such as inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin pigment, azo dyes and metal phthalocyanine dyes, and indicator nutrients such as salts of iron, magnesium, boron, copper, cobalt, molybdenum and zinc can be used.

Additives can also be perfumes, mineral or vegetable, optionally modified oils, paraffins, and nutrients (including labeled nutrients) such as iron, magnesium, boron, copper, cobalt, molybdenum, and zinc salts.

Additional components may be stabilizers, such as cold stabilizers, preservatives, antioxidants, light stabilizers or other substances that improve chemical and/or physical stability.

If necessary, other additional components may also be present, for example, protective colloids, binders, adhesives, thickeners, thixotropic agents, wetting agents, stabilizers, stabilizing agents, complexing agents. In general, the active ingredients may be combined with any solid or liquid additives commonly used for formulation purposes.

Typically, formulations contain 0.05-99% by weight, 0.01-98% by weight, preferably 0.1-95% by weight, more preferably 0.5-90% of the active ingredient, most preferably 10-70% by weight.

The formulations described above can be used to control unwanted microorganisms, where compositions containing compounds of formula (I) are used on microorganisms and/or their natural environment.

In accordance with the present invention, the compounds of formula (I) as well as salts, N-oxides, metal complexes, stereoisomers or polymorphs can be used as such or in formulations and can be mixed with known miscible substances to expand, for example, the spectrum of action or prevent the development of resistance. Useful mixants include, for example, known fungicides, insecticides, acaricides, nematicides, biopesticides, and bactericides. A mixture with other known active ingredients, such as herbicides, or with fertilizers and growth regulators, safeners and/or chemical signal agents, is also possible.

Examples of such chemical ingredients are provided below, but the list is not exhaustive. Some of these are listed by common names that are known and described, for example in the Pesticide Manual, 17th edition, or can be found on the Internet (eg www.alanwood.net/pesticides). Others are written according to systematic names in accordance with the SHRAS rules for nomenclature.

All named mixing substances of classes (A)-(O) described below may, if their functional groups permit, optionally form salts with the corresponding bases or acids, appearing as stereoisomers, even if not indicated in each case, or as polymorphs. They are also understood as specified in the document. Such examples are

A) Inhibitors of ergosterol biosynthesis, for example (A01) aldimorph, (A02) azaconazole, (A03) bitertanol, (A04) bromuconazole, (A05) cyproconazole, (A06) diclobutrazol, (A07) difenoconazole, (A08) diniconazole, (A09) diniconazole-M, (A10) dode morph, (A11) dodemorph acetate, (A12) epoxiconazole, (A13) etaconazole, (A14) fenarimol, (A15) fenbuconazole, (A16) fenhexamide, (A17) fepropidine, (A18) fenpropimorph, (A19) fluquinconazole, (A20) flurprimidol, (A21) fluconazole , (A22) flutriafol, (A23) furconazole, (A24) furconazole-cis, (A25) hexaconazole, (A26) imazalil, (A27) imazalil sulfate, (A28) imibenconazole, (A29) ipconazole, (A30) metconazole, (A31) myclobutanil, (A32) on ftifine, (A33) nuarimol, (A34) oxpoconazole, (A35) paclobutrazol, (A36) pefiirazoate, (A37) penconazole, (A38) piperalin, (A39) prochloraz, (A40) propiconazole, (A41) prothioconazole, (A42) piributicarb, (A43) pyrefenox, ( A44) quinconazole, (A45) simeconazole, (A46) spiroxamine, (A47) tebuconazole, (A48) terbinafine, (A49) tetraconazole, (A50) triadimefon, (A51) triadimenol, (A52) tridemorph, (A53) triflumizole, (A54) triforin, (A55) triticonazole . sol-5-carboxylate, (A62) N'-{5-(diformethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamide, (A63) N-ethyl-N-methyl-N'-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamide, (A64) O-[1 -(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl]-1H-imidazole-1-carbothioate, (A65) pyrisoxazole, (A66) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (A67)1-{[ 3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate (A68) 5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole [1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, (A70) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2, 4-triazol-3-thione, (A71) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (A72)1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl) oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (A73)1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (A74) 5-(allylsulfanyl)-1-{[ rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (A75) 5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-tria sol, (A76) 2-[(2S,4S,5S)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (A77l) 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, (A78) 2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (A79) 2-[ (2S,4R,5R)-1-(2,4-'dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, (A80) 2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-s-2,6,6-trimethylheptan-4-yl]- 2,4-dihydro-3H-1,2,4-triazole-3-thione, (A81) 2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-dichlorophenyl-2,6,6-trimethylheptan-4-c]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (A82) 2-[(2R,4R,5S )-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-c, (A83) 2-[(2S,4R,5S)-l-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1 ,2,4-triazol-3-thione, (A84) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (A85) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2 -ol, (A86) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol, (A87) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (A88) 2-[2-chloro -4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (A89) (2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-c]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (A90) (2R)-2-(1-chlorocyclopropyl) )-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (A91) (2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (A92) (2S)-2 -(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocytopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (A93) (1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (A94) (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (A95) 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol.

C) Respiratory chain inhibitors in complex I or II, for example, (B01) bixafen, (B02) boscalid, (B03) carboxin, (B04) cypropamide, (B05) diflumetorim, (B06) fenfuram, (B07) fluoropyram, (B08) flutlanil, (B09) fluxapiroxad, (B10) furamet pyrase, (B11) furmecyclox, (B12) isopyrase (mixture of syn-epimer racemate 1RS,4SR,9RS and anti-epimer racemate 1RS,4SR,9SR), (B13) isopyrase (anti-epimer racemate 1RS,4SR,9SR), (B14) isopyrase (anti-epimer enantiomer 1R, 4S,9S), (B15) isopyrazam (anti-epimer enantiomer 1S,4R,9R), (B16) isopyrazam (syn-epimer racemate 1RS,4SR,9RS), (B17) isopyrase (syn-epimer enantiomer 1R,4S,9R), (B18) isopyrazam (syn-epimer enantiomer 1S ,4R,9S), (B19) mepronil, (B20) oxycarboxin, (B21) penflufen, (B22) penthiopyrad, (B23) pidiflumethofen, (B24) sedaxan, (B25) tifluzamide, (B26) 1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl) -1H-pyrazole-4-carboxamide, (B27) 3-(difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide, (B28) 3-(difluoromethyl)-1N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1H-pyra sol-4-carboxamide, (B29) N-[1(2,4-dichloromethyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (B30) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, (B31) benzovindiflupyr, (B32) N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanenaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (B33) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4- tetrahydro-1,4-methanenaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (B34) 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazol-4-carboxamide, (B35) 1,3,5-trimethyl-N-( 1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (B36) 1-methyl-3-(tritoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazol-4-carboxamide, (B37) 1-methyl-3-(trifluoromethyl)-N-[( 3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (B38) 1-methyl-3-(trifluoromethyl)-N- [(38)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (B39) 3-(difluoromethyl) -1-methyl-N-(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (B40) l,3,5-trimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamide, (B42) 3) benodanil, (B44) 2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide, (B45) Isofetamide, (B46)1-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazol-4-carboxamide, (B47) N-(4'-chlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (B48) yl]-1H-pyrazole-4-carboxamide, (B50) N-(2',5'-difluorobiphenyl-2-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide, (B51) 3-(difluoromethyl)-1-methyl-N-[4'-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazol-4-carboxamide, ( B52) 5-fluoro-1,3-dimethyl-N-[4'-yl)biphenyl-2-yl]nicotinamide, (B54) 3-(difluoromethyl)-N-[4'-(3,3-Dimethylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide, (B55) N-[4'-(3,3-Dimethylbut-1- in-1-yl)biphenyl-2-yl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (B56) 3-(difluoromethyl)-N-(4'-ethynylbiphenyl-2-yl)-1-methyl-1H-pyrazole-4-carboxamide, (B57) N-(4'-ethynylbiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyr sol-4-carboxamide, (B58) 2-chloro-N-(4'-ethynylbiphenyl-2-yl)nicotinamide, (B59) 2-chloro-N-[4'-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide, (B60) 4-(difluoromethyl)-2-methyl-N-[4'-(trifluoromethyl)biphenyl-2-yl] -1,3-thiazole-5-carboxamide, (B61) 5-fluoro-N[4'-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide, (B62) 2-chloro-N-[4'-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide . carboxamide, (B65) 2-chloro-N-[4'-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotinamide, (B66) 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (B67) 1,3-dimethyl-N -[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (B68) 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (B69) 3-(difluoromethyl)-N -methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propan-2-yl]-1H-pyrazole-4-carboxamide, (B70) 3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide, (B71) 3-(difluoromethyl) -N-[(3,R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (B72) 3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4- carboxamide.

C) Complex III respiratory chain inhibitors e.g. ) fenamidone, (C11) fenamistrobin, (C12) fluphenoxystrobin, (C13) fluoroxastrobin, (C14) kresoxim-methyl, (C15) methominostrobin, (C16) mandestrobin, (C17) orysastrobin, (C18) picoxystrobin, (C19) pyraclostrobin, (C20) pyrametostrobin, (C21) ) pyraoxystrobin, (C22) pyribencarb, (C23) triclopyricarb, (C24) trifluoroxystrobin, (C25) (2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylacetamide, (C26) (2E)-2-(methoxyimino) -N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)acetamide, (C27) (2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}cetamide, (C28) (2E)-2-{ 2-[({[(1Е)-1-(3-{[(Е)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (С29) Phenaminostrobin, (С30) 5-methoxy-2-methyl-4-(2-{[({(1Е)-1-[3-(trifluoromethyl)phenyl]ethylidene}ami no)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, (C31) methyl (2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}sulfanyl)methyl]phenyl}-3-methoxyacrylate, (C32) N-(3-ethyl-3,5,5-trimethylcyclophenyl)-3-formamido-2-hydroxybenzamide, (C33) 2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (C34) 2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (C35) (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimide but)-N,3-dimethylpent-3-enamide.

D) Inhibitors of mitosis and cell division e.g. methyl, (D11) thiophanate, (D12) zoxamide, (D13) 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine, (D14) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-tri fluorophenyl) pyridazine.

E) Compounds with multicenter action, for example, (E01) Bordeaux liquid, (E02) captafol, (E03) captan, (E04) chlorthalonil, (E05) copper hydroxide, (E06) copper naphthenate, (E07) copper oxide, (E08) copper oxychloride, (E09) copper (2+) sulfate, (E10) dichlofluanide, (E1 1) dithianone, (E12) dodine, (E13) dodine neutral base, (E14) ferbam, (E15) fluorofolpet, (E16) folpet, (E17) quasatin, (E18) quasatin acetate, (E19) iminoctadine, (E20) iminoctadine albesilate, (E21) iminoctadine triacetate, (E22) man copper, (E23) mancozeb, (E24) maneb, (E25) metiram, (E26) metiram zinc, (E27) oxin-copper, (E28) propamidin, (E29) propineb, (E30) sulfur and sulfur solutions, including calcium polysulfide, (E31) thiram, (E32) tolylfluanid, (E33) zineb, (E34) ziram, (E33) anilazine.

F) Compounds capable of inducing immune protection, eg (F01) acibenzolar-b-methyl, (F02) isothianil, (F03) probenazole, (F04) thiadinil, (F05) kelp.

G) Inhibitors of amino acid and/or protein biosynthesis e.g. 4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (G09) oxytetracycline, (G10) steptomycin.

H) ATP production inhibitors, for example. (H01) fentin acetate, (H02) fentin chloride, (H03) fentin hydroxide, (H04) silthiopham.

I) Cell wall synthesis inhibitors e.g. (111) (2E)-3-(4-ter-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (112) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

J) Lipid and membrane synthesis inhibitors e.g. J11) prothiocarb, (J12) pyrazophos, (J13) quintozene, (J14) tecnazene, (J15) toclophos-methyl.

K) Inhibitors of melanin biosynthesis, e.g. (K01) carpropamide, (K02) diclocimet, (K03) phenoxanil, (K04) phthalide, (K05) pyroquilon, (K06) tolprocarb, (K07) tricyclazole.

L) Nucleic acid synthesis inhibitors e.g. metalaxyl-M (mefenoxam), (L11) ofuras, (L12) oxadixyl, (L13) oxolinic acid, (L14) octylinone.

M) Signal transduction inhibitors, e.g. (M01) chlorosolinate, (M02) fenpiclonil, (M03) fludioxonil, (M04) iprodine, (M05) procymidone, (M06) quinoxyfen, (M07) vinclozoline, (M08) proquinazid.

N) Compounds capable of acting as disconnectors, eg (N01) binapacryl, (N02) dinocap, (N03) ferimsone, (N04) fluazinam, (N05) meptyldinocap.

O) Additional compounds, e.g. (O01) benthiazole, (O02) betoxazine, (O3) capsimycin, (O04) carvone, (O05) quinomethionate, (O06) pyriophenone (chlazaphenone), (O07) kufraneb, (O08) cyflufenamide, (O09) cymoxanil, (O10) cyprosulfamide , (O11) dazomet, (O12) debacarb, (O13) dichlorphen, (O14) dichlobentiazox, (O15) dichlomesin, (O16) diphenzoquat, (O17) diphenzoquat methyl sulfate, (O18) diphenylamine, (O19) ecomat, (O20) phenpyrazamine, (O21) fenhexamine, (O22 ) flumetover, (O23) fluorimide, (O24) flusulfamide, (O25) fluthianil, (O26) fosetyl-aluminum, (O27) fosetyl-calcium, (O28) fosetyl-sodium, (O29) hexaclobenzene, (O30) irumamycin, (O31) isothianil, (O32) metasulfocarb , (O33) methyl isothiosulfonate, (O34) metrafenone, (O35) mildiomycin, (O36) natamycin, (O37) nickel dimethyldithiocarbamate, (O38) nitrotal-isopropyl, (O39) oxamocarb, (O40) oxyphentiine, (O41) pentachlorophenol and salts, (O42) phenothrin, (O43) picar butrazox (O44) phosphoric acid and its salts, (O45) propamocarb-fosetilate, (O46) propanosine sodium, (O47) pyrimorph, (O48) pyraziflumide (O49) pyrrolnitrine, (O50) tebufloquine, (O51) tecloftalam, (O52) tolnifanide, (O53) triazoxide, (O54) three chlamyd, (O55) sarylamide, (O56) (3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoate, (O57) 1-(4-{4 -[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (O58) 1-(4-{4-[(58)-5-(2,6-difluorophenyl)-4 ,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (O59) oxathiapiproline, (O60) 1-(4-meoxyphenoxy)-3,3-dimethylbutan-2-yl-1H-imidazol-1-car boxylate, (O61) 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine, (O62) 2,3-dibutyl-6-chlorothieno[2,3-c1]pyrimidin-4(3H)-one, (O63) 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrol-1,3, 5,7(2H,6H)-tetron, (064) 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone, (O65) 2-[5-methyl-3 -(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone, (O66) 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-]-yl]-1-{4-[4-(5 -phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone, (O67) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (O68) 2-chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazol- 5-yl]pyridine, (069) 2-phenylphenol and salts, (О70) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (O71) 3,4,5-trichloropyridine-2,6-dicarbonitrate, (O72) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl) )-6-methylpyridazine, (O73) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (O74) 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine, (O75) 5-amino-1,3,4-thiadiazole-2-thiol, (O76) 5-chloro-N'-phenyl-N' -(prop-2-yn-1-yl)thiophene-2-sulfonohydrazide, (O77) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (O78) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (O79) 5-methyl-6-octyl[1,2,4]triazole[1,5-a]pyrimidine- 7-amine, (O80) ethyl (27)-3-amino-2-cyano-3-phenylacrylate, (O81) N'-(4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (O82) N-(4-chlorobenzyl)-3-[3-methoxy-4-( prop-2-yn-1-yloxy)phenyl]propanamide, (O83) N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide, (O84) N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloronicotinamide, (О85) N-[-[1-( 5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide, (086) N-[-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotinamide, (О87) N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenyl acetamide, (O88) N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide, (O89) N'-{4-[(3-tert-butyl-4-cyano-1,2-thiazol-5-yl)oxy]-2-chloro-5-methylphenyl}-N-ethyl-N-methylimidoformamide, (O90) N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazol-4-carboxamide, (O91) N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl] acetyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazol-4-carboxamide, (O92) N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4 -tetrahydronaphthalen-1-yl]-1,3-thiazol-4-carboxamide, (O93) pentyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (O94) phenazine-1-carboxylic acid, (095) quinolin-8-ol, (O96) quinoline -8-ol sulfate (2:1) N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)tyl]-N2-(methylsulfonyl)valinamide, (O100) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (O101) but-3-yn-1-yl {6-[({[Z)-(1-methyl-1H-tetrazol-5 -yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (O102) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2(1H)-one), (O103) propyl 3,4,5-trihydroxybenzoate, (O104) [3-(4-chloro-2-fluorophenyl)-5-(2 ,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (O105) (8)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (O106) (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4- difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (0107) 2-fluoro-6-(trifluoromethyl)-N-[-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide, (O108) 2-(6-benzylpyridin-2-yl)quinazoline, (O109) 2-[6- (3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, (O110) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (O111) abscisic acid, (O112) N'-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2 -methylpyridin-3-yl]-N-ethyl-N-methylidimformamide, (O113) N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylidimformamide, (O114) N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methyl pyridin-3-yl}-N-ethyl-N-methylidimformamide, (O115) N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylidimformamide, (O116) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyri din-3-yl}-N-[-ethyl-N-methylidimformamide, (O117) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-[-ethyl-N-methylidimformamide, (O118) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyra sol-4-carboxamide, (O119) N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (O120) N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (O121) N-( 5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (O122) N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (O123) N-[-cyclopropyl-3-(difluoromethyl)-N- (2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (O124) N-cycloopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (O125) N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)- 5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (O126) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (O127) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyra sol-4-carboxamide, (O128) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (O129) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (O130 ) N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (O131) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (O132) N-[5-chloro-2- (trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (O133) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide, (O134) N-[2-chloro-6-(trifluoromethyl)benzyl ]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (O135) N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (O136) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl -4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (O137) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide, (O138) N'-(2,5-dimethyl-4-phenoxyphenyl)-N-[-ethyl-N-methylidimformamide, (O139) N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-[-ethyl-N-methylidimformamide, (O140) N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (O141) 9-fluoro -2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine, (O142) 2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl} propan-2-ol, (O143) 2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan- 2-ol, (O144) 4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (O145) 4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (O146) (2-chloro-6-fluorophenyl)-1,3-dimethyl-1Н-pyrazole-5-amine, (O147) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1Н-pyrazole-5-amine, (O148) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1Н -pyrazol-5-amine, (O149) 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (O150) bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (O152) N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (O153) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyra zol-5-amine, (O154) 4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (O155) 4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (0156) difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylidimformamide, (O157) N'-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylidimformamide, (O158) N'-(2,5-dimethyl-4-{3-[(2,2,2 -trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylidimformamide, (O159) N'-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylidimformamide, (O160) N'-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy }phenyl)-N-ethyl-N-methylidimformamide, (0161) N'-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylidimformamide, (0162) N'-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylide imformamide, (O163) N'-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylidimformamide, (O165) N'-(2,5-dimethyl-4-{[3-(pentafluoroepoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidofomiamide, (O166) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro- 1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (O167) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl }-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (O168) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2 -yl)piperidin-1-yl]ethanone, (O169) 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl methanesulfonate, (O170) 2-{3-[ 2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (O171) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4- (4-{(5S)-5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (O172) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5 -[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (O173) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-fluoro-6-(pro p-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (O174) 1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (O175) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl ]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-ethanone, (O176) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro -1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (O177) 2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2- oxazol-5-yl}phenyl methanesulfonate, (0178) 2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl methanesulfonate, (O179) 2- {(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (О180) 2-{(5R)-3-[2-(1-{[3,5- bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (O181) (3S,6S,7R,8R)-8-benzyl-3-{3-[(isobutyryloxy)methoxy]-4-methoxypicoline amido}-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl isobutyrate.

As described above, the compound of formula (I) may be mixed with one or more active compatible compounds selected from the insecticide/acaricide/nematicide class. which are listed by common names that are known and described in, for example, the Pesticide Manual, 17th Edition, or can be found on the Internet (eg www.alanwood.net/pesticides).

(1) Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. alanicarb, aldicarb, bendiocarb, benfuracarb, butocarboxym, butoxycarboxym, carbaryl, carbofuran, carbosulfan, ethiophencarb, fenobucarb, formetanate, furatiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pyrimicarb, propoxur, thiodicarb, thiophanox, triazamate, trimetacarb, CMS and xylylcarb or organophosphates such as acephate, azamethifos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyphos, chlorphenvinphos, chlormephos, chlorpyrifos , chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichdlovos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfotone, EPN, ethion, etoprofos, famfur, fenamiphos, fenitrothion, fenthion, fostiazate, heptenophos, imicylate, isofentphos, isopropyl O-(methoxy aminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, metidathione, mevinphos, monocrotophos, naled, ometoate, oxydemeton-methyl, parathion, parathion-methyl, phentoate, phorate, fosalon, phosmet, phosphamidon, foxim, pyrimifos-methyl, profenofos, propetam phos, prothiophos, pyraclophos, pyridafenthion, quinalphos, sulfotep, tebupyrimphos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, and vamidothione.

(2) Antagonists of the GABA chloride ion transport channel, such as organochlorides of the cyclodient, for example, chlordane and endosulfan, or phenylpyrazoles (fiproles), for example, ethiprol and finpronil.

(3) Sodium channel modulators/voltage-dependent sodium channel blockers, such as pyrethroids, e.g. da-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyfenotrin [(1R)-trans isomers], deltamethrin, empentrin [(EZ)-(1R)-isomers], esfenvalerate, etofenprox, fenpropatrin, fenvalerate, flucitrinate , flumethrin, tau-fluvalinate, halfenprox, imiprothrin, cadetrin, momftorthrin, permethrin, phenothrin [(1R)-trans isomer), pralletrin, pyrethrins (pyrethrum), resmethrin, silaflufen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomers)], tralometrin and trasfluthrin or DDT or meth oxychlor.

(4) Nicotinic acetylcholine receptor (nAChR) competitive modulators such as neonicotinoids such as acemamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiachloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifuron.

(5) Allosteric nicotinic acetylcholine receptor (nAChR) modulators such as spirosins, eg spinetoram and spinosad.

(6) Allosteric modulators of the glutamate chloride ion transport channel (GluCl), such as avermectins/milbemycins, eg abamectin, emamectin benzoate, lipemectin and milbemectin.

(7) Juvenile hormone mimics, such as juvenile hormone analogues, such as hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

(8) Active compounds with unknown or non-specific mechanisms of action, such as alkyl halides, such as methyl bromide and other alkyl halides, or chloropicrin or fluorides, or borates, or emetic tartar, or methyl isocyanate generators.

(9) Chordotonal organ TRPV channel modulators, such as pyridine azomethine derivatives, eg pimetrosine and pyrifluquinasone or flonicamid.

(10) Mouse growth inhibitors such as clofentezin, hexythiazox and difluvidazine or ethoxazole.

(11) Insect midgut microbial disruptors such as Bacillus thuringiensis subsp. israelensis, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis and Bacillus sphaericus and BT plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A 105, C ry2Ab, Vip3a, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1.

(12) Inhibitors of mitochondral ATP synthesis, such as organotin miticides, such as azocyclotin, cyhexatin and fenbutatin oxide or diafenthiuron or propargit or tetradifon.

(13) Oxidative phosphorylation breakers acting through protoconal gradient disruption, eg chlorfenapyr, DNOC and sulfluramide.

(14) A nicotinic acetylcholine receptor (nAChR) channel blocker such as bensultap, cartap hydrochloride, thiocyclam and thiosulptar sodium.

(15) Type 0 chitin biosynthesis inhibitors such as bistrifluoron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

(16) Inhibitors of chitin biosynthesis, type 1, such as buprofezin.

(17) Moult breakers (particularly in dipteran), such as cyromazine.

(1S) Ecdysone receptor antagonists such as chlormafenoside, halofenoside, methoxyfenoside and tebufenoside.

(19) Octopamine receptor antagonists such as amitraz.

(20) Inhibitors of mitochondrial complex III electron transport, such as hydramethylnon or acequinocyl or fluacripyrim or biphenazate.

(21) Mitochondrial complex I electron transport inhibitors such as METI acaricides and insecticides, eg phenazquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad or rotenone (derris).

(22) Voltage-dependent sodium channel blockers, such as indoxacarb or metaflumizone.

(23) Acetyl CoA carboxylase inhibitors such as tetronic and tetramic acid derivatives such as spirodiclofen, spiromesifen and spirotetramat.

(24) Mitochondrial complex IV electron transport inhibitors such as phosphides, eg aluminum phosphide, calcium phosphide, zinc phosphide and phosphine or cyanides.

(25) Inhibitors of mitochondrial complex II electron transport, such as beta-ketonitrile derivatives, such as cyenopyraphene and cyflumethophen or carboxanilides.

(28) Ryanodine receptor modulators such as diamides, eg chlorantraniliprole, cyantraniliprone and flubendiamide.

(29) Modulators of the chordotonal organ at an indeterminate target site, such as flonicamid.

Other active ingredients with unknown or undetermined mechanism of action, such as afidopyropene, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, quinomethionate, cryolite, cyclaniliprol, cycloxapride, cichalodiamide, dichlormesothiaz, dicofol, diflovidazine, flomethoquine, fluazaindolizin, fluensulfone, flufenerim, flufenoxystrobin, flufiprol, fluhexafon, fluopyram, fluralaner, fluxamethamide, fufenoside, guadipyr, heptafluthrin, imidaclotiz, iprodione, lotilaner, meperfluthrin, paihongding, piflubumide, pyradalil, pyrifluquinazon, pyriminotrobin, sarolaner, tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole, thioxazafen, triflumesopyrim and iodomethane; further solutions based on Bacillus firmus (I-1582, BioNeem, Votivo) and the following known active ingredients: -(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4'-piperidin]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO2003106457), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidine-4- yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO2006003494), 3-(2,5-dimethylphenyl)-4-hydroxy-S-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO2009049851), 3-(2,5-dimethylphenyl)-S-methoxy-2-oxo-1,8 -diazaspiro[4.5]dec-3-en-4-yl ethyl carbonate (known from WO2009049851), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO2004099160), 4-(but-2-yn-1-yloxy)-6-(3-chlorophenyl)pyr imidine (known from WO2003076415), PF1364 (CAS-Rev. No. 1204776-60-2), methyl 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2-methylhydrazinecarboxylate (known from WO2005085216), methyl 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-ethylhydrazinecarboxylate (known from WO2005085216), methyl 2-[2-({[3-bromo-1-(3-chloro- pyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazinecarboxylate (known from WO2005085216), methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chloro-pyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino) benzoyl]-2-ethylhydrazinecarboxylate (known from WO2005085216), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-carboxamide (known from CN102057925), 4-[5-( 3,5-dichlorophenyl)-5-(tritoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxidothietan-3-yl)benzamide (known from WO2009080250), N-[(2E)-1-[(6-chloropyridine-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,2-tritor acetamide (known from WO2012029672), 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidine-1-ium-2-olate (known from WO2009099929), 1-[(6-chloropyridin-3-yl)methyl]-4-oxo-3-phenyl- 4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate (known from WO2009099929), 4-(3-{2,6-dichloro-4-[(3,3-dichloroprop-2-en-1-yl)oxy]phenoxy}propoxy)-2-methoxy-6-(trifluoromethyl)pyrimidine (known from CN101337940), N-[2- (tert-butylcarbanoyl)-4-chloro-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-(fluoromethoxy)-1H-pyrazol-5-carboxamide (known from WO2008134969), butyl-[2-(2,4-dichlorophenyl)-3-oxo-4-oxaspiro[4.5]dec-1-en-1-yl]carbonate (specified in CN102060818), 3(E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoropropan-2-one (known from WO2013144213), N-(methylsulfonyl)-6-[2-(pyridin-3-yl)-1,3-thiazol-5-yl]pyridine-2-carboxamide ( known from WO2012000896), N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (known from WO2010051926).

The compounds of formula (I) can be used to treat certain fungal pathogens. Non-limiting examples of fungal disease pathogens that can be treated in accordance with the invention include:

diseases caused by powdery mildew pathogens, eg Blumeria spp., eg Blumeria graminis; a species of Podosphaera, for example, Podosphaera leucotricha; a species of Sphaerotheca, for example, Sphaerotheca fuliginea; Uncinula spp., eg Uncinula necator; Erysiphe spp., eg Erysiphe cichoracearu;

diseases caused by rust disease pathogens, eg Gymnosporangium spp., eg Gymnosporangium sabinae; a species of Hemileia, for example, Hemileia vastatrix; a species of Phakopsora, such as Phakopsora pachyrhizi or Phakopsora meibomiae; Puccinia species, for example Puccinia recondita, Puccinia graminis or Puccinia striiformis; Uromyces spp., e.g. Uromyces appendiculatus;

diseases caused by pathogens from the oomycete group, eg Albugo spp., eg Albugo Candida; a species of Bremia, for example, Bremia lactucae; Peronospora spp., for example Peronospora pisi or P. brassicae; a species of Phytophthora, such as Phytophthora infestans; a species of Plasmopara, for example, Plasmopara viticola; a species of Pseudoperonospora, for example Pseudoperonospora humuli or Pseudoperonospora cubensis; a species of Pythium, such as Pythium ultimum;

cucumber leaf spot diseases and vascular leaf diseases caused by, for example, Alternaria spp., eg Alternaria solani; a species of Cercospora, such as Cercospora beticola; Cladiosporium species, for example Cladiosporium cucumerinum; a species of Cochliobolus, for example, Cochliobolus sativus (conidial form: Drechslera, syn: Helminthosporium) or Cochliobolus miyabeanus; Colletotrichum spp., for example Colletotrichum lindemuthanium; a species of Cycloconium, for example, Cycloconium oleaginum; Diaporthe spp., e.g. Diaporthe citri; Elsinoe spp., e.g. Elsinoe fawcettii; Gloeosporium spp., eg Gloeosporium laeticolor; Glomerella spp., eg Glomerella cingulata; a species of Guignardia, for example, Guignardia bidwelli; a species of Leptosphaeria, for example, Leptosphaeria maculans; a species of Magnaporthe, for example, Magnaporihe grisea; a species of Microdochium, for example, Microdochium nivale; a species of Mycosphaerella, for example Mycosphaerella graminicola, Mycosphaerella arachidicola or Mycosphaerella fijiensis; a species of Phaeosphaeria, for example, Phaeosphaeria nodorum; a species of Pyrenophora, such as Pyrenophora teres or Pyrenophora tritici repentis; a species of Ramularia, such as Ramularia collo-cygni or Ramularia areola; a species of Rhynchosporium, for example, Rhynchosporium secalis; a Septoria species, for example Septoria apii or Septoria lycopersici; a species of Stagonospora, for example, Stagonospora nodorum; a Typhula species, for example, Typhula incarnata; a species of Venturia, for example, Venturia inaequalis;

diseases of the root and stem, caused, for example, by a species of Corticium, for example, Corticium graminearum; Fusarium spp., e.g. Fusarium oxysporum; a species of Gaeumannomyces, for example, Gaeumannomyces graminis; a Plasmodiophora species such as Plasmodiophora brassicae; a species of Rhizoctonia, for example, Rhizoctonia solani; a Sarocladium species, for example, Sarocladium oryzae; a species of Sclerotium, for example, Sclerotium oryzae; a species of Tapesia, for example, Tapesia acuformis; Thielaviopsis species, for example Thielaviopsis basicola; a species of Ganoderma, for example, Ganoderma lucidum;

spike and panicle diseases (including corn cobs) caused by, for example, Alternaria spp., eg Alternaria spp.; Aspergillus species, for example Aspergillus flavus; a Cladosporium species, for example Cladosporium cladosporioides; a species of Claviceps, for example, Claviceps purpurea; Fusarium spp., e.g. Fusarium culmorum; Gibberella spp., eg Gibberella zeae; a species of Monographella, for example, Monographella nivalis; species Stagnospora, for example, Stagnospora nodorum;

diseases caused by smut fungi, eg Sphacelotheca spp., eg Sphacelotheca reiliana; Tilletia spp., eg Tilletia caries or Tilletia controversy Urocystis spp., eg Urocystis occulta; view of Ustilago, for example, Ustilago nuda;

fruit rot caused, for example, by Aspergillus spp., eg Aspergillus flavus; a species of Botrytis, for example, Botrytis cinerea; a Penicillium spp., for example Penicillium expansum or Penicillium purpurogenum; Rhizopus species, for example, Rhizopus stolonifer; a species of Sclerotinia, for example, Sclerotinia sclerotiorum; Verticilium spp., e.g. Verticilium alboatrum;

rot transmitted through seeds or soil, as well as seedling diseases caused, for example, by Alternaria spp., eg Alternaria brassicicola; Aphanomyces spp., e.g. Aphanomyces euteiches; species of Ascochyta, for example, Ascochyta lentis; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium herbarum; a species of Cochliobolus, eg Cochliobolus sativus (conidial form: Drechslera, Bipolaris syn: Helminthosporium); Colletotrichum spp., such as Colletotrichum coccodes; Fusarium spp., e.g. Fusarium culmorum; Gibberella spp., eg Gibberella zeae; Macrophomina spp., for example Macrophomina phaseolina; a species of Microdochium, for example, Microdochium nivale; a species of Monographella, for example, Monographella nivalis; a species of Penicillium, for example, Penicillium expansum; Phoma species, such as Phoma lingam; Phomopsis species, for example, Phomopsis sojae; Phytophthora species, for example Phytophthora cactorum; a species of Pyrenophora, for example, Pyrenophora graminea; a species of Pyricularia, for example, Pyricularia oryzae; a species of Pythium, such as Pythium ultimum; a species of Rhizoctonia, for example, Rhizoctonia solani; Rhizopus species, for example, Rhizopus oryzae; a species of Sclerotium, for example Sclerotium rolfsii; a species of Septoria, for example, Septoria nodorum; a Typhula species, for example, Typhula incarnata; Verticillium species, for example Verticillium dahliae;

ulcers, bald patches and honeysuckle caused by, for example, a Nectria species, eg Nectria galligena;

vascular diseases caused, for example, by Monilinia species, eg Monilinia laxa;

deformations of leaves, flowers and fruits caused, for example, by an Exobasidium species, for example, Exobasidium vexans; a species of Taphrina, such as Taphrina deformans;

degenerative diseases of woody plants caused by, for example, Esc spp., eg Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranean Ganoderma spp., eg Ganoderma boninense;

flower and seed diseases caused, for example, by Botrytis spp., eg Botrytis cinerea;

diseases of plant tubers caused, for example, by Rhizoctonia spp., eg Rhizoctonia solani; Helminthosporium species, for example Helminthosporium solani;

diseases caused by bacterial pathogens, eg Xanthomonas species, eg Xanthomonas campestris pv. oryzae; Pseudomonas species, e.g. Pseudomonas syringae pv. lachrymans; Erwinia species, for example Erwinia amylovora; Ralstonia spp., e.g. Ralstonia solanacearum;

Fungal diseases on roots and stem base caused, for example, by black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina), fusarium rot or wilt, root rot and pod and branch rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), roots oyster rot (Mycoleptodiscus terrestris), neocosmospores (Neocosmospora vasinfecta), bean and stem rot (Diaporthe phaseolorum), trunk cancer (Diaporthe phaseolorum var. caulivora), late blight rot (Phytophthora megasperma), soybean stem brown rot (Phialophora gregata), mushroom rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctonia root rot, stem rot and black leg rot (Rhizoctonia solani), sclerotinia stem rot (Sclerotinia sclerotiorum), white rot (Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsis basicold).

Plants that can be treated according to the invention include: Rosaceae (e.g. pome fruits such as apples, pears, apricots, cherries, almonds and peaches), Ribesioidae, Juglandaceae, Betulaceae, Anacardiaceae, Fagaceae, Moraceae, Oleaceae, Actinidaceae, Lauraceae, Musaceae (e.g. bananas and plantations), Rubiaceae (e.g. coffee), Theaceae, Sterculiceae , Rutaceae (eg lemons, oranges and grapefruits); Vitaceae (eg grapes); Solanaceae (eg tomato, pepper), Liliaceae, Asteraceae (eg lettuce), Umbelliferae, Cruciferae, Chenopodiaceae, Cucurbitaceae (eg cucumber), Alliaceae. (eg leeks, onions), Papilionaceae (eg peas); staple crops such as Poaceae (e.g. corn, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale), Asteraceae (e.g. sunflower), Brassicaceae (e.g. white cabbage, red cabbage, broccoli, cauliflower, brussels sprouts, chinese cabbage, kohlrabi, radish, and oilseed rape, chicken, horseradish and watercress), Fabacae (eg beans, peanuts), Papilionaceae (eg soybeans), Solanaceae (eg potatoes), Chenopodiaceae (eg sugar beet, fodder beet, chard, red beet); Malvaceae (eg cotton); useful plants and ornamental plants for gardens and woodlands; and genetically modified species of each of such plants.

All plants and plant parts can be treated in accordance with the invention. Plants are herein understood to mean all plants and plant populations, such as desired and undesired wild plants or crops (including crops of natural origin). Crops can be plants that can be obtained using conventional cultivation and optimization methods or biotechnological methods and genetic engineering methods or a combination of such methods, including transgenic plants, and including plant varieties that are protected and not protected by plant breeders' rights. Plant parts are understood to mean all parts and organs of plants located above and below ground, such as cuttings, leaves, flowers and roots, examples of which include leaves, needles, stalks, stems, flowers, fruiting bodies, fruits and seeds, as well as roots, tubers and rhizomes. Plant parts also include crop material and propagative and generative material, such as cuttings, tubers, rhizomes, cuttings, and seeds.

The invention will also include a method for treating seeds, in particular seeds (dormant, primed, sprouted or even rooted and leafed) treated with at least one of the compounds of formula (I) and compositions. The developed seeds are used in methods to protect seeds and emerging plants from phytopathogenic harmful fungi. Such methods use seeds treated with at least one developed active ingredient.

It is also desirable to optimize the amount of active ingredient used to provide the best possible protection for seeds, germinated plants and emerging shoots from attack by phytopathogenic fungi, but without damaging the plants themselves by the active ingredient used. In particular, methods for seed treatment should also take into account the inherent phenotypes of transgenic plants in order to achieve optimal seed and germinating plant protection using minimal crop protection compositions.

Therefore, the present invention also relates to a method for protecting seeds, germinated plants and emerging seedlings from attacks by animal pests and/or plant pathogenic harmful microorganisms by treating the seeds with an active composition. The invention also relates to the use of compositions according to the invention for seed treatment to protect seeds, germinated plants and emerging seedlings from animal pests and/or phytopathogenic microorganisms. The invention also relates to seeds that have been treated with the developed composition for protection against animal pests and/or phytopathogenic microorganisms.

One of the advantages of this invention is that the treatment of seeds with such compositions not only protects the seeds themselves, but also subsequent plants from animal pests and/or plant pathogens. Thus, immediate treatment of the crop at the time of sowing or immediately after, protects the plants in the same way as seed treatment before sowing. It is also considered an advantage that the developed active components or compositions can also be used for transgenic seeds, in which case the plant that grows from such seeds is able to release a protein that acts against pests, herbicidal damage or abiotic stress. Treatment of such seeds with developed active ingredients or compositions, such as an insecticidal protein, may result in the control of certain pests. In this case, a further synergistic effect can be observed, which further increases the effectiveness of protection against attacks by pests, microorganisms, weeds or abiotic stress.

The compounds of formula (I) are suitable for the protection of seeds of any plant species which are used in agriculture, greenhouses, forests or horticulture. In particular, cereals (such as wheat, barley, rye, millet, oats), oilseed rape, corn, cotton, soybeans, rice, potatoes, sunflowers, beans, coffee, beets (such as sugar beets and fodder beets), peanuts, vegetables (such as tomatoes, cucumber, onions and lettuces), lawn grass and ornamental plants. Particularly significant is the treatment of wheat, soybean, oilseed rape, corn and rice seeds.

As described below, the treatment of transgenic seeds with developed active ingredients or compositions is of particular importance. This applies to plant seeds that contain at least one heterologous gene that provides for the expression of a polypeptide or protein, for example, with insecticidal properties. Such heterologous genes in transgenic seeds may arise, for example, from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. Such heterologous genes preferably originate from the species Bacillus., in which case the gene product is effective against corn borer and/or grass rootworm. Particularly preferred is the origin of the heterologous gene from Bacillus thuringiensis.

In the context of this invention, the developed composition is applicable to seeds alone or in an appropriate formulation. It is preferable to treat the seeds in a state where they are stable enough to prevent damage during treatment. In general, seeds can be processed at any time between harvest and post-sowing. It is customary to use seeds that are separated from the plant and obtained from the fruits, husks, cuttings, skins, hairs, or pulp of the fruit. For example, you can use seeds that have been harvested, cleaned and dried to a moisture content of less than 15% by weight. Alternatively, it is also possible to use seeds that, after drying, for example, have been treated with water and then dried again, or seeds immediately after priming, or seeds stored in the priming state and before germination, or seeds sown in trays, on tapes or paper.

During seed treatment, it is generally necessary to ensure that the amount of seed formulation being used and/or the amount of adjuvants is chosen such that seed germination is not affected or that the plant will not be damaged in the future. This must especially be guaranteed in the case of active ingredients which have a phytotoxic effect at certain application rates.

The compounds of formula (I) can be applied directly, ie without any other components and without dilution, in general it is preferable to use seed compositions in the form of an appropriate formulation. Appropriate formulations and methods for seed treatment are known to those skilled in the art. The compounds of formula (I) can be formulated into conventional formulations suitable for application to seeds, such as solutions, emulsions, suspensions, powders, foams, solutions, or in combination with other seed coating compositions, such as film forming materials, granulating materials, fine powders of iron or other metals, granules, coating material for non-activated seeds, as well as UVF formulations.

During seed treatment, the seeds may be coated with a polymer to facilitate germination. The polymer coating consists of a binder, wax and pigment, and one or more stabilizers in an amount sufficient to stabilize the slurry. The binder may be a polymer selected from the group consisting of vinyl acetate-ethylene copolymer, vinyl acetate homopolymer, vinyl acetate-acrylic copolymer, vinyl acrylic, acrylic, ethylene-vinyl chloride, vinyl ester maleic anhydride, or butadiene-styrene copolymer. Other similar polymers may be used.

Such formulations are developed in a known manner by mixing active ingredients or active ingredient compositions with conventional excipients, for example conventional excipients and solutions or diluents, colorants, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins, and also water.

Useful colorants that may be present in seed disinfection formulations used in accordance with the invention are all colorants that are conventional for such purposes. Any pigments that are sparingly soluble in water or dyes that are soluble in water can be used. Examples include the dyes known as Rhodamine B, C.I. pigment red 112 and C.I. solvent red 1.

Useful wetting agents that may be present in seed disinfection formulations used in accordance with the invention are all agents that promote wetting and are traditionally used to formulate active agrochemicals. Preferred for use are alkylnaphthalenesulfonates, such as diisopropyl or diisobutylnaphthalenesulfonates.

Useful dispersants and/or emulsifiers that may be present in seed disinfection formulations used in accordance with the invention are all non-ionic, anionic and cationic dispersants that are traditionally used to formulate active agrochemical components. Preferred for use are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Useful non-ionic dispersants include ethylene oxide/propylene oxide block polymers, alkylphenol polyglycol ethers and tristrirylphenol polyglycol ether and their phosphated or sulfated derivatives. Suitable anionic dispersants are lignosulfonates, polyactylate salts and arylsulfonate/formaldehyde condensates.

Defoamers that may be present in seed disinfection formulations used in accordance with the invention are all foam inhibitors that are traditionally used to formulate active agrochemical components. Silicone defoamers and magnesium stearate are preferred for use.

Preservatives that may be present in seed disinfection formulations used in accordance with the invention are all substances used for such purposes in agrochemical compositions. Examples include dichlorophen and the benzyl alcohol semiformal.

Secondary thickeners that may be present in seed disinfection formulations used in accordance with the invention are all substances used for such purposes in agrochemical compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan, modified clays, and finely divided silica.

Adhesives that may be present in seed disinfection formulations used in accordance with the invention are traditional binders that are used in seed disinfection preparations. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

The formulations for seed preparations that are used in accordance with the invention can be used to treat various types of seeds directly or after pre-dilution with water. For example, concentrates or solutions obtained by dilution with water can be used to disinfect seeds of cereals, such as wheat, barley, rye and triticale, as well as seeds of corn, soybeans, rice, oilseed rape, peas, beans, cotton, sunflowers and beets, or seeds of various other vegetables. The formulations used in accordance with the invention, or from diluted solutions, can also be used for seeds of transgenic plants. In this case, additional synergistic effects may also occur when interacting with substances formed by the expression.

For the treatment of seeds with the formulations used in accordance with the invention, or solutions prepared from them by the addition of water, all mixtures conventionally used for application to seeds are useful. The seed application procedure involves placing the seeds in a mixer, adding the required amount of the formulation as is or after pre-dilution with water, and mixing until the formulation is uniformly distributed over the seeds. If necessary, drying is carried out after application.

The rate of application of formulations used in accordance with the invention may vary over a relatively wide range. This is determined by the specific content of active ingredients in the recipe and seeds. The application rate of each individual active ingredient is usually 0.001 to 15 g per kilogram of seeds, preferably 0.01 to 5 g per kilogram of seeds.

When using a compound of formula (I) as a fungicide, the application rate may vary within a relatively wide range depending on the type of application. The application rate of the developed active components:

in case of treatment of plant parts, e.g. leaves: 0.1-10000 g/ha, preferably 10-1000 g/ha, more preferably 30-300 g/ha (in case of application by watering or spraying, it is possible to reduce the application rate, especially when inert substrates such as mineral wool or perlite are used);

in the case of seed treatment: 0.1-200 g per 100 kg of seeds, preferably 1-150 g per 100 kg of seeds, more preferably 2.5-25 g per 100 kg of seeds, even more preferably 2.5-12.5 g per 100 kg of seeds;

in the case of tillage: 0.1-10000 g/ha, preferably 1-5000 g/ha.

Such application rates are given by way of example only and are not limited for the purposes of the invention.

In some cases, the compounds of formula (I) may, at certain concentrations or application rates, also be used as herbicides, safeners, growth regulators or plant enhancers, or as microbicides, for example as fungicides, antifungals, bactericides, viricides (including compositions against viroids) or as compositions against MLOs (mycoplasmal organisms) and RLOs (rickettsia-like organisms).

The compounds of formula (I) occur in the physiological processes of plants and can therefore also be used as plant growth regulators. Plant growth regulators can have various effects on plants. The effect of the substances is particularly dependent on the time of application in relation to the stage of development of the plant, the variety of plants, as well as the amount of active ingredient applied to the plants or their habitat and the type of application. In each case, the growth regulators must have a certain desired effect on crops.

Effects on growth regulation include early germination, improved emergence, more developed root system and/or improved root growth, increased tillering capacity, more productive shoots, onset of flowering, increased plant growth and/or biomass, stem shortening, improved shoot growth, number of kernels/cobs, number of ears/m ² , number of underground shoots and/or number of flowers, improved yield weight percentage to full plant weight, larger leaves, less dead grassroots, improved phyllotaxis, early ripening/early fruit ripening, uniform ripening, longer grain filling time, better fruit ripening, larger fruit/vegetable size, growth tolerance and reduced lodging.

Increased or improved yield refers to total biomass per hectare, yield per hectare, grain/fruit weight, seed size and/or hectoliter weight, and improved product quality, including:

improved processability in terms of size distribution (grain, fruit, etc.), uniform maturation, grain moisture filling, better grinding, improved winemaking, improved brewing, increased juice, yield, digestibility, sedimentation number, number of falls, pod stability, storage stability, improved fiber length/strength/uniformity, increased quality of milk and/or meat from silage-fed animals, adaptation for cooking and frying;

also including improved competitiveness in terms of fruit/grain quality, size distribution (grains, fruits, etc.), improved storage/shelf life, hardness/softness, taste (aroma, texture, etc.), class (size, shape, number of fruits, etc.), number of fruits/fruits per branch, crunchiness, freshness, waxing, incidence of physiological disorders, color, etc.;

also including increased amounts of desired components such as protein content, fatty acids, oil content, oil quality, amino acid composition, sugar content, acid content (pH), sugar to acid ratio (Brix), polyphenols, starch content, nutritional value, gluten content/index, energy value, taste, etc.;

and also including a reduced amount of undesirable components such as less mycotoxins, less aphthatoxins, geosmin levels, phenolic aroma, polyphenol oxidases and peroxidases, nitrate content, etc.

Plant growth regulating compounds can be used, for example, to slow down the vegetative growth of plants. Such growth retardations have an economic effect, for example in the case of grass, as this makes it possible to reduce the frequency of cutting grass in ornamental gardens, parks and sports fields, on roadsides, at airports or in the case of fruit crops. Also important is the suppression of the growth of cereals and woody plants on roadsides and near pipelines or power lines, or in areas where strong plant growth is undesirable.

Also important is the use of growth regulators to inhibit the longitudinal growth of cereals. This reduces or completely eliminates the risk of plant lodging before harvest. In addition, in the case of cereals, growth regulators can strengthen the stems, which also counteracts lodging. Using Growth Regulators to shorten and strengthen stems allows you to place higher amounts of fertilizer to increase yield without the risk of crop lodging.

In the case of many crops, the suppression of vegetative growth allows the plantings to be concentrated and therefore it is possible to achieve a higher yield based on the soil surface. Another advantage for smaller plants obtained in this way is that cultivation and harvesting are easier.

Decreased vegetative plant growth can also result in increased or improved yield, as nutrients and assimilation have more benefits for flower and fruit formation than for the vegetative parts of the plant.

Alternatively, growth regulators can also be used to promote vegetative growth. This is a great advantage when harvesting the vegetative parts of the plant. However, promoting vegetative growth can also promote generative growth by producing more assimilates, resulting in more or larger fruits.

Moreover, beneficial effects on yield growth can be achieved through improved food use efficiency, especially nitrogen (N) use efficiency, phosphorus (P) use efficiency, water use efficiency, improved transport, respiration and/or CO ₂ assimilation rate, improved nodule formation, improved Ca metabolism, etc.

Similarly, growth regulators can be used to change the composition of plants, which in turn can lead to improved crop quality. Under the influence of growth regulators, parthenocarp fruits can form. In addition, you can influence the gender of flowers. Pollen sterility can also be reduced, which is very important for reproduction and the production of hybrid seeds.

The use of growth regulators can control the branching of plants. On the one hand, by interrupting apical dominance, the development of side shoots can be promoted, which can be very desirable in particular for the cultivation of ornamental plants, also in combination with growth inhibition. On the other hand, however, it is possible to inhibit the growth of side shoots. In particular, this effect is interesting, for example, in the cultivation of tobacco or tomatoes.

Under the influence of growth regulators, the number of leaves on plants can also be controlled to achieve plant defoliation at the desired time. Such defoliation plays a major role in the mechanical harvest of cotton, but is also of interest in facilitating the harvest of other crops, such as in winemaking. Plant defoliation is also used to reduce plant transpiration prior to transplanting.

Moreover, growth regulators can also modulate plant senescence, which can result in a longer green leaf period, longer seed filling phase, improved yield quality, and so on.

Similarly, growth regulators can be used to control fruit opening. On the one hand, premature opening of the fruit can be prevented. On the other hand, it is possible to promote opening of the fruit or even premature cessation of flowering to achieve the desired weight ("thinning"). In addition, growth regulators can be used during harvest to reduce the effort required to separate the fruit in the case of mechanical harvesting or to facilitate manual harvesting.

Growth regulators can also be used to achieve faster or delayed maturation of harvested material before or after harvest. This is advantageous in particular, since allows you to optimally adapt to the requirements of the market. Moreover, in some cases, growth regulators can improve fruit color. In addition, growth regulators can also be used to synchronize maturation with a certain period of time. This establishes prerequisites for fully mechanical or manual harvesting in a single operation, such as in the case of tobacco, tomatoes or coffee.

By using growth regulators, it is also possible to influence plant seed or bud settling so that plants such as pineapples or ornamental plants in greenhouses, for example, germinate, sprout or flower at a time when they would not normally do so. In areas where there is a risk of frost, it may be desirable to delay bud formation or seed germination with growth regulators to prevent damage from late frosts.

Finally, growth regulators can improve plant resistance to frost, drought, or severe salinity. This allows you to grow plants in regions that are not usually suitable for such a procedure.

The compounds of formula (I) also exhibit a strong plant hardening effect. Accordingly, they can be used to mobilize the plant's defenses against attack by undesirable microorganisms.

Substances that strengthen plants (increase resistance), in this context are substances capable of stimulating the defense system of plants so that the treated plants, in the event of planting undesirable microorganisms, subsequently show a high level of resistance to such microorganisms.

Also in the context of this invention, the physiological effects of the plant include the following:

Abiotic stress tolerance, including heat or cold tolerance, drought tolerance and recovery from drought, water use efficiency (relative to reduced water consumption), flood tolerance, ozone stress and UV tolerance, chemical tolerance such as heavy metals, salts, pesticides, etc.

Biotic stress tolerance, including increased resistance to fungi and increased resistance to nematodes, viruses and bacteria. In the context of the present invention, biotic stress tolerance preferably includes increased resistance to fungi and increased resistance to nematodes.

Increased plant vigor, consisting of plant health/plant quality and seed vigor, reduced planting problems, improved appearance, improved recovery from periods of stress, improved pigmentation (e.g. chlorophyll content, greening effect, etc.) and improved photosynthetic efficiency.

In addition, the compounds of formula (I) can reduce the content of mycotoxins in the collected material and food products and feed made from it. In particular, mycotoxins include, but are not limited to, the following: deoxynavalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2- and HT2-toxin, fumonisins, zearalenones, moniliformin, fusarin, diacetoxyscirpenol (DAS), beauvericin, enniatin, fusaroproliferin, fusarenol, ochratoxins, patulins, ergot alkaloids and aflatoxins, the sources of which can be, for example, the following fungi: Fusarium spp., such as F. acuminatum, F. asiaticum, F. avenaceum, F. crookwellense, F. culmorum, F. graminearum (Gibberella zeae), F. equiseti, F. fujikoroi, F. musarum, F. oxys porum, F. proliferatum, F. poae, F. pseudograminearum, F. sambucinum, F. scirpi, F. semitectum, F. solani, F. sporotrichoides, F. langsethiae, F. subglutinans, F. tricinctum, F. verticillioides, etc., as well as Aspergillus species, such as A. flavus, A. parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, Penicillium spp., such as P. verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, P. roqueforti, Claviceps spp., such as C. purpurea, C. fusiformis, C. paspali, C. africana , species Stachybotrys and others.

The compounds of formula (I) can also be used to protect materials, to protect industrial materials from attack and destruction by phytopathogenic fungi.

In addition, the compounds of formula (I) can be used as anti-rot compositions alone or together with other active ingredients.

In this context, industrial materials are understood as non-living materials that have been prepared for use in industry. For example, industrial materials that need to be protected from microbial alteration or degradation by the designed compositions can be adhesives, glue, paper, wallpaper and board/cardboard, textiles, carpets, leather, wood, fibers and fabrics, paints and plastic products, cooling lubricants, and other materials that can be infected or destroyed by microorganisms. Parts of industrial plants and buildings, such as water cooling circuits, cooling and heating systems, ventilation and air conditioning devices, which may be affected by microbial growth, may also be included in the materials that must be protected. Industrial materials covered by this invention preferably include adhesives, dimensions, paper and cards, leather, wood, paints, coolants and heat transfer fluids, more preferably wood.

The compounds of formula (I) can prevent side effects such as rotting, decomposition, discolouration, discoloration or mold formation.

In the case of wood treatment, the compounds of formula (I) can also be used to prevent fungal diseases that usually appear on or inside the wood. The term "wood" means all types of wood and all types of wood products intended for construction, such as solid wood, durable wood, laminated wood and plywood. The wood treatment method according to the invention basically consists of the inclusion of a composition according to the invention; this includes, for example, direct application, spraying, dipping, injecting, or other appropriate means.

In addition, the compounds of formula (I) can be used to protect objects that come into contact with salt water or hard water, especially hulls, nets, nets, buildings, moorings and signal systems, from biological fouling.

Also, compounds of formula (I) can be used to protect stored goods. Stored goods are understood to be natural substances or vegetables or products of animal origin or processed products of natural origin and for which long-term protection is desirable.

Stored plant products, e.g. plants or parts of plants, such as stems, leaves, tubers, seeds, fruits, can be protected immediately after harvest or after processing by (pre-) drying, moistening, chopping, grinding, pressing or baking. Stored goods also include wood, whether unprocessed, such as construction timber, power poles and barriers, or in finished goods, such as furniture. Stored goods of animal origin include, for example, hides, skins, furs and hair. Designed compositions can prevent side effects such as rotting, decomposition, discoloration, discoloration or mold.

Microorganisms capable of degrading or altering industrial materials include, for example, bacteria, fungi, yeasts, algae, and mucus. The compounds of formula (I) preferably act against fungi, especially moulds, fungi that discolor or destroy wood (Ascomycetes, Basidiomycetes, Deuteromycetes and Zygomycetes), and against mucus and algae. Examples include microorganisms of the following classes: Alternaria, such as Alternaria tenuis; Aspergillus, such as Aspergillus niger, Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana; Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor, Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma, such as Trichoderma viride; Ophiostoma spp., Ceratocystis spp., Humicola spp., Petriella spp., Trichurus spp., Coriolus spp., Gloeophyllum spp., Pleurotus spp., Porta spp., Serpula spp. and Tyromyces spp., Cladosporium spp., Paecilomyces spp. Mucor spp., Escherichia, such as Escherichia coli; Pseudomonas, such as Pseudomonas aeruginosa; Staphylococcus, such as Staphylococcus aureus, Candida spp. and Saccharomyces spp., such as Saccharomyces cerevisae.

In addition, the compounds of formula (I) also have a very good antifungal activity. They have a broad spectrum of antifungal activity, especially against dermatophytes and yeasts, molds and biphasic fungi (for example, against Candida species, such as Candida albicans, Candida glabrata), and Epidermophyton floccosum, Aspergillus species, such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species, such as Trichophyton mentagrophytes, Microsporon such as Microsporon canis and audouinii. The listing of such fungi in no way constitutes a limitation on the fungal spectrum covered, and is for illustrative purposes only.

The compounds can also be used to control important fungal pathogens in fisheries and crayfish farming, eg saprolegnia diclina in trout, saprolegnia parasitica in crayfish.

Therefore, the compounds of formula (I) can be used for medical and non-medical purposes.

The compounds of formula (I) may be used as they are in their formulation form, or forms prepared from them may be used, such as ready-to-use solutions, suspensions, reconstitutable powders, pastes, soluble powders, dusts and granules. Application is carried out in the traditional way, such as watering, spraying, fine spraying, spreading over the field, pollination, aeration, application and others. It is also possible to use the active ingredients in the ultra-low volume method or to introduce the solution of the active ingredient / the active ingredient itself into the soil. Plant seeds can also be processed.

It is possible to treat all plants and their parts in accordance with the invention, preferably wild plant species and plant varieties, or those obtained by traditional methods of biological cultivation, such as crossing or fusion of protoplasts, as well as parts thereof. In a further preferred embodiment, transgenic plants and genetically engineered plant varieties are processed, if applicable, together with conventional methods (genetically modified organisms) and parts thereof. The terms "parts" and "plant parts" are explained above. More preferably, plants of varieties that are commercially available or used are treated according to the invention. Plant varieties are understood as plants that have new properties ("features") and have been obtained by conventional cultivation, mutagenesis or recombinant DNA techniques. They can be cultivars, varieties, bio- or genotypes.

According to the invention, the treatment method can be used to treat genetically modified organisms (GMOs), such as plants or seeds. Genetically modified plants (or transgenic plants) are plants whose heterologous gene has been stably integrated into the genome. The term "heterologous gene" means a gene that is provided or created outside of a plant and, when introduced into the nuclear, chloroplastic, or mitochondrial genome, provides the transformed plant with new or improved agronomic or other properties by expressing a desired protein or polypeptide, or by down-regulating or suppressing other genes that are present in the plant (for example, by desensitization technology, co-suppression technology, RNA interference technology - RINA or microRNA technology - miRNA). A heterologous gene located in the genome is also called a transgene. A transgene is identified by its location in the plant genome and is called a transformational or transgenic event.

Plants and plant varieties that are preferably to be treated in accordance with the invention include all plants that have genetic material that imparts certain advantageous, beneficial traits to such plants (obtained by cultivation and/or biotechnological methods).

Plants and plant varieties, which are also preferably to be treated in accordance with the invention, are resistant to one or more biotic stresses, i.e. said plants show better protection against animal and microbial pests, such as against nematodes, insects, mice, phytopathogenic fungi, bacteria, viruses and/or viroids.

Plants and plant varieties that can also be treated in accordance with the invention are plants that are resistant to one or more abiotic stresses. Abiotic stress conditions may include, for example, drought, exposure to cold temperatures, exposure to heat, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozone exposure, high light exposure, limited nitrogen nutrient availability, limited phosphorus nutrient availability, lack of shade.

Plants and plant varieties that can also be treated in accordance with the invention are plants that have increased yield characteristics. Increased yield in said plants may result, for example, from improved plant physiology, growth and development, such as water use efficiency, moisture retention efficiency, improved nutrient utilization, increased carbon assimilation, improved photosynthesis, increased germination efficiency, and accelerated maturation. Also, the improved architecture of the plant (in a state of stress and under conditions without stress) can also affect the exit, including, but not limited, early flowering, flowering control for the production of hybrid seeds, the power of the seedlings, the size of the plant, the quantity and the distance between the inter -navigations, the growth of the roots, the size of the seed, the size of the pod, the amount of pep With the completion of seeds, reduced flights of seeds, reduced scraping of pods and resistance to hopping. Yield properties also include seed composition, such as hydrocarbon content and composition, for example, cotton or starch, protein content, oil content and composition, nutritional value, reduction of anti-nutritional compounds, improved processability, and better storage stability.

Plants that can be treated in accordance with the invention are hybrid plants that already have heterosis or hybrid vigor characteristics, resulting in generally higher yield, vigor, health and resistance to biotic and abiotic stress).

Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) that can be treated in accordance with the invention are herbicide-resistant plants, that is, plants that are resistant to one or more herbicides. Such plants can be obtained by gene transformation or plant breeding techniques that convey such herbicide resistance.

Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering) that can be treated in accordance with the invention are transgenic plants resistant to insects, that is, plants that are resistant to attack by certain target insects. Such plants can be obtained by gene transformation or plant breeding techniques that convey such insect resistance.

Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering) that can be treated in accordance with the invention are transgenic plants resistant to insects, that is, plants resistant to abiotic stresses. Such plants can be obtained by gene transformation or plant breeding techniques that convey such stress tolerance.

Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) show altered quantity, quality and/or storage stability of the harvested products and/or altered properties of specific components of the harvested products.

Plants or plant varieties (obtained by plant biotechnology, such as genetic engineering) that can be treated in accordance with the invention are plants, such as cotton plants, with altered fiber characteristics. Such plants can be obtained by gene transformation or plant breeding techniques that convey such altered fiber characteristics.

Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering) that can be treated in accordance with the invention are plants, such as oilseed rape or corresponding ornamental cabbage species with altered oil profile characteristics. Such plants can be obtained by gene transformation or by plant breeding techniques that convey such altered characteristics of the oilseed profile.

Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering) that can be treated in accordance with the invention are plants, such as oilseed rape or corresponding types of ornamental cabbage with modified seed cleavage characteristics. Such plants can be obtained by gene transformation or plant breeding that transmit mutations, such as seed cleavage characteristics, and include plants such as oilseed rape with delayed or reduced seed cleavage.

Plants or plant varieties (obtained by plant biotechnology, such as genetic engineering) that can be treated in accordance with the invention are plants, such as tobacco, with altered post-translational protein modification patterns.

Accordingly, the compounds of the present invention are illustrated in Tables 1 and 2.

The table below shows non-exhaustive examples of compounds in accordance with the invention. In the following examples, M+1 (or M-1) means a molecular ion peak of plus or minus 1 amu (atomic mass unit), respectively, as observed in the ¹ H-NMR mass spectrometry data of the selected examples listed in the ¹ H-NMR Peak List. For each signal peak, the δ-values in ppm and the number of protons are given in parentheses.

To calibrate the chemical shift for the ¹ H spectrum, we use tetramethylsilane and/or the chemical shift of the solvent used, especially in the case of spectra measured in DMSO. Therefore, a tetramethylsilane peak may appear in the NMR peak lists, but not necessarily.

The ¹ H-NMR peak lists are similar to the classic ¹ H-NMR replicas and therefore typically contain all 15 peaks that are listed in the classic NMR interpretation.

Additionally, like classic ¹ H-NMR copies, they can show solvent signals, stereoisomers of target compounds that are also the subject of the invention, and/or impurity peaks.

Table 1 shows the compounds of general formula (I)

Table 2 shows compounds of general formula (Ia), where R ^x , R ^y , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and A are defined.

The compounds of this invention, as defined by formula (I) and/or in Tables 1 and 2, can be prepared in a known manner, in various ways, as described in Schemes 1-4.

Scheme 1

A compound of formula 1a can be synthesized by treating a compound of formula 3 with trimethylorthoformate and PTSA followed by reaction with various secondary amines (HNR ¹ R ² ) as described in US20110130282.

Compound 1 is an important intermediate for the synthesis of the compound of formula 1a. The literature describes various methods for the synthesis of the compound of formula 1, such as,

Method 1: From the appropriate benzoyl chloride using a ZnCl ₂ or AlCl ₃ catalyst in the presence of dichloromethane as described in Helvitachimica Act XXIX (1946), pp. 1413-1424, and Tetrahedron, 56 (2000), pp. 7199-7203

Method 2: From the appropriate benzoic acid in the presence of an acid catalyst such as (a) trifluoromethane sulfonic acid as described in Tetrahedron, 56 (2000), pp. 7199-7203; (b) graphite and methane sulfonic acids as described in Synthesis 13 (2004), pp. 2165-2168; (c) graphite sulfonic acid and p-toluene as described in Helvetiva Chimica act 88 (2005) pages 2282-2287; (d) 1-perfluorobutanesulfonic acid as described in Synthesis 10 (2000), pp. 1427-1430.

Method 3: From an appropriate benzoic acid derivative in the presence of metal triflates such as copper triflate, gallium triflate or antimonium triflate or ytterbium triflate or scandium triflate or bismuth triflate as described in Green chemistry, 4 (2002), pp. 129-133 or in Tetrahedron, 56 (2000), pp. 6 63-64 65, or Bull chemical society of Jpn 73 (2000), pp. 2325-2333.

Method 4: From the appropriate substituted benzoic acid in the presence of P2O5 as such or absorbed on silica gel as described in Tetrahedron letters 49 (2008), pp. 6715-6719.

Scheme 2

A compound of formula 1a can be synthesized with a properly substituted 2a followed by the same methods as described in Scheme 1. The corresponding intermediate 2a can be synthesized from phenyl acetonitrile in the presence of alkalis such as sodium hydroxide or sodium tert butoxide or sodium hydride followed by oxidation with H ₂ O ₂ /mCPBA in the presence of aqueous KOH as described in (J. Org. Chem 1983, 48, 4097-98, J. Org. Chem. 1983, 48, 4087-4096)

Scheme 3

The compound of formula 1a can also be synthesized using the Suzuki reaction by treating the compound of formula 6 with an appropriate substituted benzyl halide as described in Bioorganic & Medicinal Chemistry Letters, 14(4), pp. 1023-1026; 2004.

The compound of formula 6 can be synthesized by treating the bromine derivative 5 with bis(pincolato)diborane using palladium acetate and a PdCl ₂ (dppf) DCM complex in dioxane in good yield.

Scheme 4

A compound of formula 1 can be synthesized by treating a phenylboronic acid derivative 7 with a compound of formula 8, where X is a carboxylic acid activator, for example, and Y is the starting material of an amine group, such as a nitro group or an NHCOCH ₃ group, in the presence of alkalis such as sodium carbonate, a palladium catalyst and a surfactant, such as sodium dodecyl sulfate, as described in Synthesis, 13, (2007), page 197 0-1980.

The present invention is further illustrated in the following non-exhaustive examples. The structures of the new compounds were confirmed by NMR and/or other relevant assays indicated.

EXAMPLE 1

Preparation of N'-(4-(3,5-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide

Step A: N-(4-(3,5-dichlorobenzyl)-2,5-dimethylphenyl)acetamide

Triethylsilane (2.78 ml, 17.40 mmol) was added to a suspension of N-(4-(3,5-dichlorobenzoyl)-2,5-dimethylphenyl)acetamide (0.9 g, 2.68 mmol) in dichloromethane (15 ml) at 0°C. The reaction mixture was stirred for 10 minutes. Boron trifluoride etherate (2.090 g, 14.72 mmol) was added dropwise to this reaction mixture. The reaction mixture was stirred for 36 hours at room temperature. After completion of the reaction, the reaction mixture was neutralized with solid sodium bicarbonate and then extracted with dichloromethane (3×200 ml). The combined organic phases were dried in anhydrous Na ₂ SO ₄ . The mixture was filtered and concentrated under reduced pressure. Thereafter, the residues were purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to give N-(4-(3,5-dichlorobenzyl)-2,5-dimethylphenyl)acetamide (0.7 g) as a solid. LCMS (M+H) 323.23

Step B: 4-(3,5-dichlorobenzyl)-2,5-dimethylaniline

To a suspension of N-(4-(3,5-dichlorobenzyl)-2,5-dimethylphenyl)acetamide (0.9 g, 2.79 mmol) in water (10 ml): ethanol (10 ml), sodium hydroxide (3.35 g, 84 mmol) was charged and the reaction mixture was heated to reflux (100°C) for 36 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane. The combined organic phases were dried in anhydrous Na ₂ SO ₄ . The mixture was filtered and evaporated under reduced pressure. Thereafter, the residues were purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to give the desired 4-(3,5-dichlorobenzyl)-2,5-dimethylaniline (0.4 g) as a gum. LCMS (M+H) 281.29

Step C: Preparation of N'-(4-(3,5-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide

A solution of 4-(3,5-dichlorobenzyl)-2,5-dimethylalaniline (0.500 g, 1.784 mmol) in trimethyl orthoformate (10.00 ml) with p-toluenesulfonic acid monohydrate (0.017 g, 0.089 mmol) was stirred at 103°C for 4 hours. The reaction mixture was concentrated under reduced pressure to give an intermediate which was then taken up in 1,4-dioxane (10 ml). Was added N-ethylmethylamine (1.551 ml, 17.84 mmol) and the reaction mixture was heated to 103°C for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give a precipitate, which was then purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to obtain the desired N'-(4-(3,5-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide (0.210 g) as a gum. LCMS (M+H) 350.35, ¹ H-NMR(400 MHz, DMSO-d6) δ 7.61 (bs, 1H), 7.40 (t 1H), 7.12 (d 2H), 6.90 (s, 1H), 6.58 (s, 1H), 3.87 (s, 2H), 3.49-3.32 (bs , 2H), 2.92 (s, 3H), 2.12 (s, 3H), 2.07 (s, 3H), 1.11 (t„ 3H)

EXAMPLE 2

Preparation of N'-(4-(4-bromobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide

Step A: Preparation of N-(4-(4-bromobenzyl)-2,5-dimethylphenyl)acetamide

Triethylsilane (3.02 g, 26.0 mmol) was added to a suspension of N-(4-(4-bromobenzoyl)-2,5-dimethylphenyl)acetamide (1.5 g, 4.33 mmol) in dichloromethane (30 ml) at 0°C. After stirring the reaction mixture for 10 minutes, boron trifluoride etherate (3.69 g, 26.0 mmol) was added dropwise to the reaction mixture. After the addition, the reaction mixture was stirred for 36 hours at room temperature. After completion of the reaction, the reaction mixture was neutralized with solid sodium bicarbonate and then extracted with dichloromethane (3×200 ml). The combined organic phases were dried in anhydrous Na ₂ SO ₄ . The mixture was filtered and concentrated under reduced pressure. The mixture was filtered and evaporated under reduced pressure. Thereafter, the residues were purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to give N-(4-(4-bromobenzyl)-2,5-dimethylphenyl)acetamide (0.7 g) as a gum. LCMS (M+H) 333.24

Step B: Preparation of 4-(4-bromobenzyl)-2,5-dimethylaniline

To a suspension of (4-amino-2,5-dimethylphenyl)(4-bromophenyl)methanone (0.7 g, 2.301 mmol) in a solution of ethanol (21 ml) and water (9 ml), potassium hydroxide (3.87 g, 69.0 mmol) was charged and the reaction mixture was heated to reflux (100°C) for 36 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with dichloromethane. The combined organic phases were dried in anhydrous Na ₂ SO ₄ . The mixture was filtered and evaporated under reduced pressure. Thereafter, the residues were purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to give the desired 4-(4-bromobenzyl)-2,5-dimethylaniline (0.45 g) as a gum. LCMS (M+H) 291.20

Step C: Preparation of N'-(4-(4-bromobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide

A solution of 4-(4-bromobenzyl)-2,5-dimethylalaniline (0.4 g, 1.378 mmol) in trimethyl orthoformate (15.00 ml) with p-toluenesulfonic acid monohydrate (0.013 g, 0.069 mmol) was stirred at 103°C for 4 hours. The reaction mixture was concentrated under reduced pressure to obtain an intermediate product, which was then placed in 1,4-dioxane (15 ml). Was added N-ethylmethylamine (1.198 ml, 13.78 mmol) and the reaction mixture was heated to 103°C for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give a precipitate, which was then purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to obtain the desired N'-(4-(4-bromobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide (0.4 g) as a gum. ¹ H-NMR(400 MHz, CHLOROFORM-D) δ 7.42 (bs, 1H), 7.35 (d, 2H), 6.98 (d, 2H), 6.86 (s, 1H), 6.58 (s, 1H), 3.84 (s, 2H), 3.59-3.18 (bs, 2H), 3.01 (s, 3H), 2.21 (s.3H), 2.18 (s.3H), 1.21 (t.3H)

EXAMPLE 3

N'-(4-(3,4-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide Step A: Preparation of N-(4-(3,4-dichlorobenzyl)-2,5-dimethylphenyl)acetamide

Triethylsilane (1.245 g, 10.71 mmol) was added to a suspension of N-(4-(3,4-dichlorobenzoyl)-2,5-dimethylphenyl)acetamide (0.6 g, 17.85 mmol) in dichloromethane (30 ml) at 0°C. After stirring the reaction mixture for 10 minutes, boron trifluoride etherate (1.520 g, 10.71 mmol) was added dropwise to the reaction mixture. After the addition, the reaction mixture was stirred for 36 hours at room temperature. After completion of the reaction, the reaction mixture was neutralized with solid sodium bicarbonate and then extracted with dichloromethane (3×200 ml). The combined organic phases were dried in anhydrous Na ₂ SO ₄ . The mixture was filtered and concentrated under reduced pressure. The mixture was filtered and evaporated under reduced pressure. Thereafter, the residues were purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to give N-(4-(3,4-dichlorobenzyl)-2,5-dimethylphenyl)acetamide (0.4 g) as a gum. LCMS (M+H) 323.23

Step B: Preparation of 4-(3,4-dichlorobenzyl)-2,5-dimethylaniline

Potassium hydroxide (2.86 g, 51.0 mmol) was charged to a suspension of (4-amino-2,5-dimethylphenyl)(3,4-dichlorobenzyl)methanone (0.5 g, 1.700 mmol) in a solution of ethanol (10 ml) and water (3 ml) and the reaction mixture was heated to reflux (100°C) for 36 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with dichloromethane. The combined organic phases were dried in anhydrous Na ₂ SO ₄ . The mixture was filtered and evaporated under reduced pressure. Thereafter, the residues were purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to give the desired 4-(3,4-dichlorobenzyl)-2,5-dimethylaniline (0.2 g) as a gum. LCMS (M+H) 281.20

Step C: Preparation of N'-(4-(3,4-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide

A solution of 4-(3,4-dichlorobenzyl)-2,5-dimethylalaniline (0.150 g, 0.535 mmol) in trimethyl orthoformate (10.00 mL) with p-toluenesulfonic acid monohydrate (5.09 g, 0.027 mmol) was stirred at 103°C for 4 hours. The reaction mixture was concentrated under reduced pressure to give an intermediate which was then taken up in 1,4-dioxane (10 ml). Was added N-ethylmethylamine (0,465 ml, 5.35 mmol)and the reaction mixture was heated to 103°C for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give a precipitate, which was then purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to obtain the desired N'-(4-(3,4-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide (0.13 g) as a gum. ¹ H-NMR(400 MHz, DMSO-d6) δ 7.60 (bs, 1H), 7.52 (d, 1H), 7.33 (d, 1H), 7.09 (dd, 8.0 Hz, 1H), 6.88 (s, 1H), 6.57 (s, 1H), 3.85 (s, 2H), 3.48-3.3 0 (bs, 2H), 2.91 (s, 3H), 2.11 (s, 3H), 2.07 (s, 3H), 1.11 (t, 3H).

EXAMPLE 4

N'-(2,5-dimethyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide

Step A: N-(2,5-dimethyl-4-(3-methylbenzyl)phenyl)acetamide

Triethylsilane (2.98 g, 25.6 mmol) was added to a suspension of N-(2,5-dimethyl-4-(3-methylbenzoyl)phenyl)acetamide (1.5 g, 4.33 mmol) in dichloromethane (30 ml) at 0°C. After stirring the reaction mixture for 10 minutes, boron trifluoride etherate (4.16 g, 29.3 mmol) was added dropwise to the reaction mixture. After the addition, the reaction mixture was stirred for 36 hours at room temperature. After completion of the reaction, the reaction mixture was neutralized with solid sodium bicarbonate and then extracted with dichloromethane (3×200 ml). The combined organic phases were dried in anhydrous Na ₂ SO ₄ . The mixture was filtered and concentrated under reduced pressure. Thereafter, the residues were purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to give N-(2,5-dimethyl-4-(3-methylbenzyl)phenyl)acetamide (0.8 g) as a gum. LCMS (M+H) 268.37

Step B: Preparation of 2,5-dimethyl-4-(3-methylbenzyl)aniline

To a suspension of 1M-(2,5-dimethyl-4-(3-methylbenzyl)phenyl)acetamide (0.7 g, 2.62 mmol) in a solution of ethanol (21 ml) and water (9 ml), potassium hydroxide (4.41 g, 79 mmol) was charged and the reaction mixture was heated to reflux (100°C) for 36 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with dichloromethane. The combined organic phases were dried in anhydrous Na ₂ SO ₄ . The mixture was filtered and evaporated under reduced pressure. Thereafter, the residues were purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to give the desired 2,5-dimethyl-4-(3-methylbenzyl)aniline (0.4 g) as a gum. LCMS (M+H) 226.34

Step C: Preparation of N'-(2,5-dimethyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide

A solution of 2,5-dimethyl-4-(3-methylbenzyl)aniline (0.3 g, 1.331 mmol) in trimethyl orthoformate (10 mL) with p-toluenesulfonic acid monohydrate (0.013 g, 0.067 mmol) was stirred at 103° C. for 4 hours. The reaction mixture was concentrated under reduced pressure to give an intermediate which was then taken up in 1,4-dioxane (10 ml). Was added N-ethylmethylamine (1.157 ml, 13.31 mmol) and the reaction mixture was heated to 103°C for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give a precipitate, which was then purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to obtain N'-(2,5-dimethyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide (0.160 g) as a gum. ¹ H-NMR(400 MHz, DMSO-d6) δ 7.58 (bs, 1H), 7.13 (t, 7.6 Hz, 1H), 6.96 (d, 7.9 Hz, 1H), 6.92 (s, 1H), 6.89 (d, 1H), 6.85 (s, 1H), 6.54 (s, 1H), 3 .79 (s, 2H), 3.42 (bs, 2H), 2.91 (s, 3H), 2.24 (s, 3H), 2.10 (2s, 6H), 1.11 (t, 3H)

EXAMPLE 5

N'-(4-(4-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide

Step A: Preparation of N-(4-(4-chlorobenzyl)-2,5-dimethylphenyl)acetamide

Triethylsilane (4.16 g, 35.8 mmol) was added to a suspension of N-(4-(4-chlorobenzoyl)-2,5-dimethylphenyl)acetamide (1.8 g, 5.96 mmol) in dichloromethane (40 ml) at 0°C. After stirring the reaction mixture for 10 minutes, boron trifluoride etherate (5.08 g, 35.8 mmol) was added dropwise to the reaction mixture. After the addition, the reaction mixture was stirred for 36 hours at room temperature. After completion of the reaction, the reaction mixture was neutralized with solid sodium bicarbonate and then extracted with dichloromethane (3×200 ml). The combined organic phases were dried in anhydrous Na ₂ SO ₄ . The mixture was filtered and concentrated under reduced pressure. The mixture was filtered and evaporated under reduced pressure. Thereafter, the residues were purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to give N-(4-(4-chlorobenzyl)-2,5-dimethylphenyl)acetamide (1.5 g) as a solid. LCMS (M+H) 288.79.

Step B: Preparation of 4-(4-chlorobenzyl)-2,5-dimethylaniline

To a suspension of N-(4-(4-chlorobenzyl)-2,5-dimethylphenyl)acetamide (1.3 g, 4.52 mmol) in a solution of ethanol (21 ml) and water (9 ml), potassium hydroxide (7.60 g, 136 mmol) was charged and the reaction mixture was heated to reflux (100°C) for 36 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with dichloromethane. The combined organic phases were dried in anhydrous Na ₂ SO ₄ . The mixture was filtered and evaporated under reduced pressure. Thereafter, the residues were purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to give the desired 4-(4-chlorobenzyl)-2,5-dimethylaniline (0.8 g) as a gum. LCMS (M+H) 246.75

Step C: Preparation of N'-(4-(4-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide

A solution of 4-(4-chlorobenzyl)-2,5-dimethylalaniline (0.7 g, 2.85 mmol) in trimethyl orthoformate (10.00 ml) with p-toluenesulfonic acid monohydrate (0.027 g, 0.142 mmol) was stirred at 103°C for 4 hours. The reaction mixture was concentrated under reduced pressure to give an intermediate which was then taken up in 1,4-dioxane (10 ml). Was added N-ethylmethylamine (2,476 ml, 28.5 mmol)and the reaction mixture was heated to 103°C for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give a precipitate, which was then purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to obtain the desired N'-(4-(4-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide (0.3 g) as a gum. ¹ H-NMR(400 MHz, DMSO-d6) δ 7.66-7.43 (bs, 1H), 7.30 (d, 2H), 7.14-7.08 (d, 2H), 6.85 (s, 1H), 6.54 (s, 1H), 3.82 (s, 2H), 3.47-3.32 (bs, 2H), 2.99-2.79 (s, 3H), 2.09 (s, 3H), 2.06 (s, 3H), 1.10 (t, 3H)

EXAMPLE 6

N'-(2,5-dimethyl-4-(4-(methylthio)benzyl)phenyl)-N-ethyl-N-methylformimidamide

Step A: Preparation of N-(2,5-dimethyl-4-(4-(methylthio)benzyl)phenyl)acetamide

Triethylsilane (3.78 g, 32.5 mmol) was added to a suspension of N-(2,5-dimethyl-4-(4-(methylthio)benzoyl)phenyl)acetamide (1.7 g, 5.42 mmol) in dichloromethane (30 ml) at 0°C. After stirring the reaction mixture for 10 minutes, boron trifluoride etherate (4.62 g, 32.5 mmol) was added dropwise to the reaction mixture. After the addition, the reaction mixture was stirred for 36 hours at room temperature. After completion of the reaction, the reaction mixture was neutralized with solid sodium bicarbonate and then extracted with dichloromethane (3×200 ml). The combined organic phases were dried in anhydrous Na ₂ SO ₄ . The mixture was filtered and concentrated under reduced pressure. Thereafter, the residues were purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to give N-(2,5-dimethyl-4-(4-(methylthio)benzyl)phenyl)acetamide (0.7 g) as a gum. LCMS (M+H) 297.90

Step B: Preparation of 2,5-dimethyl-4-(4-(methylthio)benzyl)aniline

To a suspension of N-(2,5-dimethyl-4-(4-(methylthio)benzyl)phenyl)acetamide (0.7 g, 2.338 mmol) in a solution of ethanol (21 ml) and water (9 ml), potassium hydroxide (3.93 g, 70.1 mmol) was charged and the reaction mixture was heated to reflux (100°C) for 36 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with dichloromethane. The combined organic phases were dried in anhydrous Na ₂ SO ₄ . The mixture was filtered and evaporated under reduced pressure. Thereafter, the residues were purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to give the desired 2,5-dimethyl-4-(4-(methylthio)benzyl)aniline (0.4 g) as a solid. LCMS (M+H) 256.90

Step C: Preparation of N'-(2,5-dimethyl-4-(4-(methylthio)benzyl)phenyl)-N-ethyl-N-methylformimidamide A solution of 2,5-dimethyl-4-(4-(methylthio)benzyl)aniline (0.3 g, 1.166 mmol) in trimethyl orthoformate (10 mL) with p-toluenesulfonic acid monohydrate (0.011 g, 0.0 58 mmol) was stirred at 103°C for 4 hours. The reaction mixture was concentrated under reduced pressure to give an intermediate which was then taken up in 1,4-dioxane (10.00 ml). Was added N-ethylmethylamine (1,013 ml, 11.66 mmol)and the reaction mixture was heated to 103°C for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give a precipitate, which was then purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to obtain the desired N'-(2,5-dimethyl-4-(4-(methylthio)benzyl)phenyl)-N-ethyl-N-methylformimidamide (0.21 g) as a gum. 1H-NMR(400 MHz, DMSO-d6) δ 7.59-7.44 (bs, 1H), 7.12 (d, 2H), 7.01 (d, 2H), 6.83-6.78 (s, 1H), 6.51 (s, 1H), 3.75 (s, 2H), 3.42-3.30 (bs, 2H), 2.87 (s, 3Н), 2.39 (s, 3Н), 2.06 (s, 3Н), 2.05 (s, 3Н), 1.07 (t, 3Н)

EXAMPLE 7

N'-(2,5-dimethyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide

Step A: Preparation of N-(2,5-dimethyl-4-(4-methylbenzyl)phenyl)acetamide

Triethylsilane (3.47 g, 29.9 mmol) was added to a suspension of N-(2,5-dimethyl-4-(4-(methylbenzoyl)phenyl)acetamide (1.4 g, 4.98 mmol) in dichloromethane (30 ml) at 0° C. After stirring the reaction mixture for 10 minutes, boron trifluoride etherate (4.24 g, 29.9 mmol) was added dropwise to the reaction mixture ol).After the addition, the reaction mixture was stirred for 36 hours at room temperature.After completion of the reaction, the reaction mixture was neutralized with solid sodium bicarbonate and then extracted with dichloromethane (3×200 ml).The combined organic phases were dried in anhydrous Na₂SO₄. The mixture was filtered and concentrated under reduced pressure. The mixture was filtered and evaporated under reduced pressure. Thereafter, the residues were purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to give N-(2,5-dimethyl-4-(4-methylbenzyl)phenyl)acetamide (0.9 g) as a solid. LCMS (M+H) 268.37

Step B: Preparation of 2,5-dimethyl-4-(4-methylbenzyl)aniline

To a suspension of N-(2,5-dimethyl-4-(4-methylbenzyl)phenyl)acetamide (0.7 g, 2.62 mmol) in a solution of ethanol (21 ml) and water (9 ml), potassium hydroxide (4.41 g, 79 mmol) was charged and the reaction mixture was heated to reflux (100°C) for 36 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with dichloromethane. The combined organic phases were dried in anhydrous Na ₂ SO ₄ . The mixture was filtered and evaporated under reduced pressure. Thereafter, the residues were purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to give the desired 2,5-dimethyl-4-(4-methylbenzyl)aniline (0.28 g) as a gum. LCMS (M+H) 226.37

Step C: Preparation of N'-(2,5-dimethyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide

A solution of 2,5-dimethyl-4-(4-methylbenzyl)aniline (0.3 g, 1.331 mmol) in trimethyl orthoformate (10 ml) with p-toluenesulfonic acid monohydrate (0.013 g, 0.067 mmol) was stirred at 103° C. for 4 hours. The reaction mixture was concentrated under reduced pressure to give an intermediate which was then taken up in 1,4-dioxane (10 ml). Was added N-ethylmethylamine (1.157 ml, 13.31 mmol) and the reaction mixture was heated to 103°C for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give a precipitate, which was then purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to obtain N'-(2,5-dimethyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide (0.160 g) as a gum. ¹ H-NMR(400 MHz, DMSO-d6) δ 7.56 (bs, 1Н), 7.04 (d, 2Н), 6.97 (d, 2Н), 6.82 (s, 1Н), 6.53 (s, 1H), 3.79 (s, 2Н), 3.33 (bs, 2Н), 2.90 (s, 3Н), 2.2 3 (s, 3Н), 2.14-2.04 (2s, 6Н), 1.10 (t, 3Н)

EXAMPLE 8

N'-(2-bromo-4-(4-bromobenzyl)-3,6-dimethylphenyl)-N-ethyl-N-methylformimidamide

Step A and step B were performed as described in the examples above.

Step C: Preparation of N'-(2-bromo-4-(4-bromobenzyl)-3,6-dimethylphenyl)-N-ethyl-N-methylformimidamide

A solution of 4-(bromo-(4-bromophenyl)methyl)-2,5-dimethylalaniline (0.5 g, 1.355 mmol) in trimethyl orthoformate (30.0 ml) with p-toluenesulfonic acid monohydrate (0.013 g, 0.068 mmol) was stirred at 103°C for 4 hours. The reaction mixture was concentrated under reduced pressure to obtain an intermediate product, which was then placed in 1,4-dioxane (30 ml). Was added N-ethylmethylamine (1,178 ml, 13.55 mmol)and the reaction mixture was heated to 103°C for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give a precipitate, which was then purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to obtain the desired N'-(2-bromo-4-(4-bromobenzyl)-3,6-dimethylphenyl)-N-ethyl-N-methylformimidamide (0.2 g) as a gum. ¹ H-NMR(400 MHz, DMSO-d6) δ 7.45 (d, 2H), 7.40-7.23 (bs, 1H), 7.05 (d, 2H), 6.96 (s, 1H), 3.96-3.86 (s, 2H), 3.50-3.36 (bs, 1H), 3.29-3.19 (bs, 1Н), 2.91 (s, 3Н), 2.18 (s, 3Н), 2.05 (s, 3Н), 1.11 (bs, 3Н)

EXAMPLE 9

N'-(4-(3-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide

Step A: Preparation of N-(4-(3-chlorobenzyl)-2,5-dimethylphenyl)acetamide

Triethylsilane (8.05 g, 69.3 mmol) was added to a suspension of N-(4-(3-chlorobenzoyl)-2,5-dimethylphenyl)acetamide (3.8 g, 12.59 mmol) in dichloromethane (40 ml) at 0°C. After stirring the reaction mixture for 10 minutes, boron trifluoride etherate (8.04 g, 56.7 mmol) was added dropwise to the reaction mixture. After the addition, the reaction mixture was stirred for 36 hours at room temperature. After completion of the reaction, the reaction mixture was neutralized with solid sodium bicarbonate and then extracted with dichloromethane (3×200 ml). The combined organic phases were dried in anhydrous Na ₂ SO ₄ . The mixture was filtered and concentrated under reduced pressure. Thereafter, the residues were purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to give N-(4-(3-chlorobenzyl)-2,5-dimethylphenyl)acetamide (2.5 g) as a solid. LCMS (M+H) 288.79

Step B: Preparation of 4-(3-chlorobenzyl)-2,5-dimethylaniline

To a suspension of N-(4-(3-chlorobenzyl)-2,5-dimethylphenyl)acetamide (4.6 g, 15.98 mmol) in a solution of ethanol (80 ml) and water (20 ml), potassium hydroxide (26.9 g, 480 mmol) was charged and the reaction mixture was heated to reflux (100°C) for 36 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with dichloromethane. The combined organic phases were dried in anhydrous Na ₂ SO ₄ . The mixture was filtered and evaporated under reduced pressure. Thereafter, the residues were purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to give the desired 4-(3-chlorobenzyl)-2,5-dimethylaniline (2.5 g) as a gum. LCMS (M+H) 246.75

Step C: Preparation of N'-(4-(3-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide

A solution of 4-(3-chlorobenzyl)-2,5-dimethylalaniline (0.8 g, 3.26 mmol) in trimethyl orthoformate (30.0 ml) with p-toluenesulfonic acid monohydrate (0.031 g, 0.163 mmol) was stirred at 103°C for 4 hours. The reaction mixture was concentrated under reduced pressure to obtain an intermediate product, which was then placed in 1,4-dioxane (30 ml). Was added N-ethylmethylamine (2.83 ml, 32.6 mmol) and the reaction mixture was heated to 103°C for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give a precipitate, which was then purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to obtain the desired N'-(4-(3-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide (0.3 g) as a gum. ¹ H-NMR(400 MHz, DMSO-d6) δ 7.68-7.42 (bs, 1H), 7.28 (d, 1H), 7.21 (dd, 1H), 7.11 (s, 1H), 7.08 (d, 1H), 6.87 (s, 1H), 6.56 (s, 1H), 3.85 (s, 2H ), 3.49-3.34 (bs, 1H), 3.32-3.19 (bs, 1H), 2.91 (s, 3H), 2.11 (s, 3H), 2.07 (s, 3H), 1.10 (t, 3H)

EXAMPLE 10

N'-(2,5-dimethyl-4-(4-(methylsulfonyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide

Step A and step B were performed as described in the examples above.

Step C: Preparation of N'-(2,5-dimethyl-4-(4-(methylsulfonyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide

A solution of 2,5-dimethyl-4-(4-(methylsulfonyl)benzyl)aniline (0.3 g, 1.037 mmol) in trimethyl orthoformate (15 mL) with p-toluenesulfonic acid monohydrate (0.020 g, 0.104 mmol) was stirred at 100° C. for 4 hours. After completion of the reaction, the volatiles were evaporated. The precipitate was added to 1,4-dioxane (15.00 ml) and N-ethylmethylamine (0.270 g, 3.11 mmol) was added. The reaction mixture was heated to 100°C for 4 hours. After completion of the reaction, the dioxane was evaporated and the residue was purified by HPLC to give N'-(2,5-dimethyl-4-(4-(methylsulfonyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide (240 mg) as a gum. 1H NMR (400 MHz, DMSO-d6) δ=7.81 (d, 2H), 7.55 (bs, 1H), 7.36 (d, 2H), 6.89 (s, 1H), 6.56 (s, 1H), 3.95 (s, 2H), 3.35-3.29 (m, 2H), 3.15 (s, 3H ), 2.90 (s, 3Н), 2.10 (s, 3Н), 2.08 (s, 3Н), 1.10 (t, 3Н); LCMS (M+H) 359.15

EXAMPLE 11

N'-(2,5-dimethyl-4-(4-(methylsulfonyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide

Step A and step B were performed as described in the examples above.

Step C: Preparation of N'-(2,5-dimethyl-4-(4-(methylsulfonyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide

To a solution of N'-(2,5-dimethyl-4-(4-(methylthio)benzyl)phenyl)-N-ethyl-N-methylformimidamide (0.3 g, 0.919 mmol) in ethanol (5 ml) was added oxone (0.282 g, 0.919 mmol) and the mixture was heated at 65°C for 2 hours. After completion of the reaction, the reaction mixture was filtered, the filtrate was evaporated to give a precipitate, which was then purified on a column to give N'-(2,5-dimethyl-4-(4-(methylsulfonyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide (0.25 g); 1Н NMR (400 MHz, DMSO-d6) δ 7.57-7.55 (m, 3Н), 7.29 (d, 2Н), 6.88 (s, 1Н), 6.55 (s, 1Н), 3.90 (s, 2Н), 3.35-3.29 (m, 2Н), 2.90 (s, 3Н), 2.68 ( s, 3Н), 2.09 (s, 3Н), 2.08 (s, 3Н), 1.10 (t, 3Н); LCMS (M+H) 343.20

EXAMPLE 12

N'-[4-(3-bromo-2-torbenzyl)-2,5-dimethylphenyl]-N-methylformimidamide

Step A and step B were performed as described in the examples above.

Step C: Preparation of N'-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide

To a solution of 4-(3-bromo-2-fluorobenzyl)-2,5-dimethialinyl (1.5 g, 4.87 mmol) in trimethyl orthoformate (10 ml) was added p-toluenesulfonic acid monohydrate (0.926 g, 4.87 mmol) and the mixture was stirred for 4 hours at 103°C. Then the reaction mixture was concentrated under reduced pressure to obtain an intermediate product. 1,4-dioxane (10.00 ml) and methylamine (20.02 ml, 40.0 mmol) were added to the intermediate. The reaction mixture was again heated to 103°C for 2.0 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain a crude product. Неочищенный продукт был очищен с помощью флэш-хроматографии с использованием гексан: этил ацетата для получения N'-(4-(3-бром-2-фторбензил)-2,5-диметилфенил)-N-метилформимидамида(400 мг) в виде смолы.. ¹ H-NMR(400 МГц, ДМСО-d6) δ 7.61 (s, 1H), 7.56-7.49 (m, 1H), 7.05 (t, 1H), 7.03-6.96 (m, 1Н), 6.81 (s, 1H), 6.61 (s, 1H), 3.88 (s, 2Н), 3.64-3.57 (m, 4Н), 3.54-3.34 (4Н), 2.11 (s, 3Н), 2.07 (s, 3Н)

EXAMPLE 13

N'-[2-chloro-4-(3-fluorobenzyl)-5-methylphenyl]-N-methylimidoformamide

Step A and step B were performed as described in the examples above.

Step C: Preparation of N'-(2-chloro-4-(3-fluorobenzyl)-5-methylphenyl)-N-methylformimidamide

To a solution of 2-chloro-4-(3-fluorobenzyl)-5-methylaniline (1.0 g, 4.00 mmol) in trimethyl orthoformate (10 ml) was added p-toluenesulfonic acid monohydrate (0.038 g, 0.200 mmol) and the mixture was stirred for 4 hours at 103°C. Then the reaction mixture was concentrated under reduced pressure to obtain an intermediate product. 1,4-dioxane (10.00 ml) and methylamine (20.02 ml, 40.0 mmol) were added to the intermediate. The reaction mixture was again heated to 103°C for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain a crude product. The crude product was purified by flash chromatography using hexane:ethyl acetate to give N'-(2-chloro-4-(3-fluorobenzyl)-5-methylphenyl)-N-methylformimidamide (600 mg) as a gum. ¹ H-NMR(400 MHz, DMSO-d6) δ 7.60 (d, 1H), 7.31 (td, 1H), 7.22-7.12 (1H), 7.09 (s, 1H), 7.05-6.88 (m, 3H), 6.72 (s, 1H), 3.88 (s, 2H), 2.77 (d, 3Н), 2.10 (s, 3Н)

EXAMPLE 14

4-(3-Chloro-4-fluorobenzyl)-2,5-dimethyl-N-[(Z)-morpholin-4-ylmethylden]aniline

Step A and step B were performed as described in the examples above.

Step C: Preparation of N-(4-(3-chloro-4-fluorobenzyl)-2,5-dimethylphenyl)-1-morpholinomethanimine

To a solution of 4-(3-chloro-4-fluorobenzyl)-2,5-dimethylaniline (0.3 g, 1.137 mmol) in trimethyl orthoformate (10 ml) was added p-toluenesulfonic acid monohydrate (10.82 g, 0.057 mmol) and the mixture was stirred for 4 hours at 103°C. The reaction mixture was then concentrated under reduced pressure to give a residue, which was then taken up in 1,4-dioxane (10.00 ml). Morpholine (0.991 ml, 11.37 mmol) was added and the reaction mixture was heated to 103° C. for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain a precipitate. The residue was purified by flash chromatography using hexane:ethyl acetate to give N-(4-(3-chloro-4-fluorobenzyl)-2,5-dimethylphenyl)-1-morpholinemethanimine (270 mg) as a gum. ¹ H-NMR(400 MHz, DMSO-d6) δ 7.61 (s, 1H), 7.37-7.26 (m, 1H), 7.24 (dd, 1H), 7.15-7.00 (m, 1H), 6.88 (s, 1H), 6.60 (s, 1H), 3.83 (s, 2H), 3.68- 3.55 (m, 4H), 3.44 (br, 4H), 2.10 (s, 3H), 2.07 (s, 3H)

EXAMPLE 15

4-(3-Chloro-4-fluorobenzyl)-2,5-dimethyl-N-[(Z)-piperidin-1-ylmethylidene]aniline

Step A and step B were performed as described in the examples above.

Step C: Preparation of N-(4-(3-chloro-4-fluorobenzyl)-2,5-dimethylphenyl)-1-(piperidin-1-yl)methanimine

To a solution of 4-(3-chloro-4-fluorobenzyl)-2,5-dimethialinyl (0.3 g, 1.137 mmol) in trimethyl orthoformate (10 ml) was added p-toluenesulfonic acid monohydrate (10.82 g, 0.057 mmol) and the mixture was stirred for 4 hours at 103°C. Then the reaction mixture was concentrated under reduced pressure to obtain a precipitate. 1,4-dioxane (10 ml) and piperidine (0.969 g, 11.37 ml) were added to the residue and the reaction mixture was heated to 103° C. for 2 hours. After completion of the reaction, the volatiles were evaporated under reduced pressure to obtain a crude product. The crude product was purified by flash chromatography using hexane:ethyl acetate to give N-(4-(3-chloro-4-fluorobenzyl)-2,5-dimethylphenyl)-1-(piperidin-1-yl)methanimine (301 mg) as a gum. ¹ H-NMR (400 MHz, DMSO-d6) δ 7.53 (s, 1H), 7.29 (dd, 1H), 7.24 (dd, 1H), 7.15–7.00 (m, 1H), 6.86 (s, 1H), 6.56 (s, 1H), 3.82 (s, 2H), 3.59–3.32 ( 4H), 2.09 (s, 3H), 2.06 (s, 3H), 1.67-1.54 (m, 2H), 1.54-1.41 (m, 4H)

EXAMPLE 16

4-(3-bromo-2-fluorobenzyl)-2,5-dimethyl-N-[(Z)-morpholin-4-ylmethylden]aniline

Step A and step B were performed as described in the examples above.

Step C: Preparation of N-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-1-morpholinomethanimine

To a solution of 4-(3-bromo-2-fluorobenzyl)-2,5-dimethialinyl (0.25 g, 0.811 mmol) in trimethyl orthoformate (10 ml) was added p-toluenesulfonic acid monohydrate (7.71 g, 0.041 mmol) and the mixture was stirred for 4 hours at 103°C. Then the reaction mixture was concentrated under reduced pressure to obtain an intermediate product. 1,4-dioxane (10 ml) and morpholine (0.71 g, 8.11 ml) were added to the intermediate product and the mixture was heated to 103° C. for 2 hours. After completion of the reaction, the volatiles were evaporated under reduced pressure to obtain a crude product. The crude product was purified by flash chromatography using hexane:ethyl acetate to give N-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-1-morpholino methanimine (250 mg) as a gum. ¹ H-NMR(400 MHz, DMSO-d6) δ 7.61 (s, 1H), 7.56-7.49 (m, 1H), 7.05 (t, 1H), 7.03-6.96 (m, 1H), 6.81 (s, 1H), 6.61 (s, 1H), 3.88 (s, 2H), 3.64- 3.57 (m, 4H), 3.54-3.34 (4H), 2.11 (s, 3H), 2.07 (s, 3H)

EXAMPLE 17

4-(3-bromo-2-fluorobenzyl)-2,5-dimethyl-N-[(Z)-piperidin-1-ylmethylden]aniline

Step A and step B were performed as described in the examples above.

Step C: Preparation of N-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-1-(piperidin-1-yl)methanimine

To a solution of 4-(3-bromo-2-fluorobenzyl)-2,5-dimethialinyl (0.25 g, 0.811 mmol) in trimethyl orthoformate (10 ml) was added p-toluenesulfonic acid monohydrate (7.71 g, 0.041 mmol) and the mixture was stirred for 4 hours at 103°C. Then the reaction mixture was concentrated under reduced pressure to obtain an intermediate product. 1,4-dioxane (10 ml) and piperidine (0.691 g, 8.11 ml) were added to the intermediate product and the reaction mixture was heated again to 103° C. for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain a crude product. The crude product was purified by flash chromatography using hexane:ethyl acetate to give N-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-1-(piperidin-1-yl)methanimine (280 mg) as a gum. ¹ H-NMR (400 MHz, DMSO-d6) δ 7.54 (s, 1H), 7.53-7.47 (m, 1H), 7.05 (t, 1H), 7.03-6.94 (m, 1H), 6.79 (s, 1H), 6.58 (s, 1H), 3.87 (s, 2H), 3.59- 3.32 (4Н), 2.10 (s, 3Н), 2.07 (s, 3Н), 1.66-1.55 (m, 2Н), 1.55-1.41 (m, 4Н)

EXAMPLE 18

N-ethyl-N'-[4-(4-fluorobenzyl)-2,5-dimethylphenyl]-N-methylimideformamide

Step A and step B were performed as described in the examples above.

Step C: Preparation of N-ethyl-N'-(4-(4-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide

To a solution of 4-(4-fluorobenzyl)-2,5-methylaniline (0.3 g, 1.308 mmol) in trimethyl orthoformate (10 ml) was added p-toluenesulfonic acid monohydrate (0.012 g, 0.065 mmol) and the mixture was stirred for 4 hours at 103°C. Then the reaction mixture was concentrated under reduced pressure to obtain an intermediate product. 1,4-dioxane (10 ml) and N-ethylmethylamine (1.137 g, 13.08 ml) were added to the intermediate product and the reaction mixture was again heated to 103° C. for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to obtain a crude product. The crude product was purified by flash chromatography using hexane:ethyl acetate to give N-ethyl-N'-(4-(4-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide (0.3 g) as a gum.

EXAMPLE 19

N-ethyl-N'-[4-(3-methoxybenzyl)-2,5-dimethylphenyl]-N-methylimideformamide

Step A: Preparation of N'-(2,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)phenyl)-N-ethyl-N-methylformimidamide

To a solution of N'-(4-bromo-2,5-dimethylphenyl)-N-ethyl-N-methylimideformamide (2.7 g, 10.03 mmol) in 1,4-dioxane (27 ml) were added DIBORANE PINACOLONE (5.09 g, 20.06 mmol) and potassium acetate (3.94 g, 40.1 mmol). Nitrogen gas was purged for 20 minutes and then PdCl ₂ (dppf)-CH ₂ Cl ₂ adduct catalyst (0.819 g, 1.003 mmol) in nitrogen was added and the reaction mixture was heated to 110° C. for 2 hours. After the reaction, the reaction mixture was concentrated under reduced pressure to obtain a crude product. The crude product was purified by flash chromatography using hexane:ethyl acetate to give the desired N'-(2,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)phenyl)-N-ethyl-N-methylformimidamide (2.5 g) as a gum. LCMS (M+H) 317.25

Step B: Preparation of N-ethyl-N'-(4-(3-methoxybenzyl)-2,5-dimethylphenyl)-N-methylformimidamide

A solution of N'-(2,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)phenyl)-N-ethyl-N-methylformimidamide (0.45 g, 1.423 mmol), 1-(bromomethyl)-3-methoxybenzene (0.429 g, 2.134 mmol) and potassium carbonate (0.590 g, 4 .27 mmol) in a solution of 1,4-dioxane (10 ml) and water (0.01 ml) was purified with nitrogen over 20 minutes, Pd(Ph ₃ p) ₄ (0.164 g, 0.142 mmol) was added to the reaction mixture, and the reaction mixture was heated to 110°C for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the crude product was purified by preparatory HPLC to give N-ethyl-N'-(4-(3-methoxybenzyl)-2,5-dimethylphenyl)-N-methylformimidamide (0.3 g) as a gum. ¹ H-NMR(400 MHz, DMSO-d6) δ 7.59-7.44 (bs, 1H), 7.12 (d, 2H), 7.01 (d, 2H), 6.83-6.78 (s, 1H), 6.51 (s, 1H), 3.75 (s, 2H), 3.42-3.30 (bs, 2H), 2.87 (s, 3Н), 2.39 (s, 3Н), 2.06 (s, 3Н), 2.05 (s, 3Н), 1.07 (t, 3Н)

EXAMPLE 20

N-ethyl-N'-(4-(methoxy(phenyl)methyl)-2,5-dimethylphenyl)-N-methyl formimidamide

A solution of (4-amino-2,5-dimethylphenyl)(phenyl)methanol (0.7 g, 3.08 mmol) in trimethyl orthoformate (20 ml) with p-toluenesulfonic acid monohydrate (0.029 g, 0.154 mmol) was stirred for 4 hours at 103°C. Then the reaction mixture was concentrated under reduced pressure to obtain an intermediate product. 1,4-dioxane (20 ml) and N-ethylmethylamine (2.68 g, 30.8 ml) were added to the intermediate product and the reaction mixture was again heated to 103° C. for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give a precipitate, which was then purified by silica gel capillary chromatography using hexane:ethyl acetate as eluent to obtain N-ethyl-N'-(4-(methoxy(phenyl)methyl)-2,5-dimethylphenyl)-N-methylformimidamide (0.4 g) as a gum. ¹ H-NMR (400 MHz, DMSO-d6) δ 7.60 (bs, 1H), 7.36-7.18 (m, 5H), 7.03 (s, 1H), 6.52 (s, 1H), 5.35 (s, 1H), 3.48-3.34 (bs, 1H), 3.32-3.24 (bs, 1H), 3.20 (s, 3H), 2.91 (s, 3H), 2.14 (s, 3H), 2.11 (s, 3H), 1.11 (t, 3H)

EXAMPLE 21

N'-(2,5-dimethyl-4-(2-phenyl-1,3-dithiolan-2-yl)phenyl)-N-ethyl-N-methyl formimidamide

Step A: Preparation of N'-(2,5-dimethyl-4-(2-phenyl-1,3-dithiolan-2-yl)phenyl)acetamide

To a solution of N-(4-benzoyl-2,5-dimethylphenyl)acetamide (1.5 g, 5.61 mmol) in anhydrous CH ₂ Cl ₂ (25 ml) were added ethane-1,2-dithiol (1.057 g, 11.22 mmol) and acetic acid (0.642 ml, 11.22 mmol), the mixture was cooled to 0 ° C, followed by the addition of boron trifluoride e terate (0.782 ml, 6.17 mmol) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane followed by quenching by dropping the reaction mixture into an aqueous NaOH solution, the mixture was separated, the combined organic layer was dried over anhydrous Na ₂ SO ₄ and concentrated. The crude product was purified by capillary chromatography to give N-(2,5-dimethyl-4-(2-phenyl-1,3-dithiolan-2-yl)phenyl)acetamide (1.8 g). LCMS (M+H) 344.50

Step B: Preparation of 2,5-dimethyl-4-(2-phenyl-1,3-dithiolan-2-yl)aniline:

To a solution of N-(2,5-dimethyl-4-(2-phenyl-1,3-dithiolan-2-yl)phenyl)acetamide (2.75 g, 8.01 mmol) in ethanol (25 ml) and water (20.00 ml) was added potassium hydroxide solution (8.98 g, 160 mmol) and the reaction mixture was heated to 90°C for 15 hours. The reaction mixture was evaporated under reduced pressure; the precipitate was diluted with water (150 ml) and extracted with ethyl acetate (3×150 ml). The combined organic layer was dried over anhydrous sodium sulfate and concentrated. The crude compound was purified by capillary chromatography to give 2,5-dimethyl-4-(2-phenyl-1,3-dithiolan-2-yl)aniline (1.2 g). LCMS (M+H) 302

Step C: Preparation of N'-(2,5-dimethyl-4-(2-phenyl-1,3-dithiolan-2-yl)phenyl)-N-ethyl-N-methylformimidamide

To a solution of 2,5-dimethyl-4-(2-phenyl-1,3-dithiolan-2-yl)aniline (270 g, 0.896 mmol) in trimethyl orthoformate (25 ml) was added PTSA (10 mg) and the reaction mixture was heated to 103°C for 4 hours. The solution was evaporated under reduced pressure. The precipitate was mixed with dioxane (25.00 ml) followed by the addition of the reaction mixture of N-ethylmethylamine (0.779 ml, 8.96 mmol), the reaction mixture was heated at 103°C for 2 hours. After conversion of the starting material was completed, the reaction mixture was concentrated under reduced pressure, the crude compound was purified by preparatory HPLC to give N'-(2,5-dimethyl-4-(2-phenyl-1,3-dithiolan-2-yl)phenyl)-N-ethyl-N-methylformimidamide (220 mg). ¹ H-NMR (400 MHz, DMSO-d6) δ 7.79 (s, 1H), 7.64 (s, 1H), 7.38 (d, 2H), 7.23-7.27 (m, 2H), 7.16-7.20 (m, 1H), 6.52 (s, 1H), 3.51-3.40 (3H), 3.4 0-3.32 (3H), 2.91 (s, 3H), 2.20 (s, 3H), 1.74 (s, 3H), 1.11 (t, 3H)

As described above, the compounds of general formula (I) show a very high antifungal activity, which is shown against various phytopathogenic fungi that attack important agricultural crops. The compounds of this invention have been evaluated for activity against one or more of:

Examples of biological tests (IN VITRO TEST)

Example 1: Pyricularia oryzae (rice blast): The compound was diluted in 0.3% DMSO and then added to potato glucose agar medium just prior to application to Petri dishes. 5 ml of the medium with compound at the desired concentration were dispensed into 60 mm sterile Petri dishes. After solidification, each dish was seeded with 5 mm mycelium discs taken from the outer edge of an actively growing hazardous culture plate. The plates were placed in growth chambers at 25° C. and 60% relative humidity for seven days and radial growth was measured. Connections 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 54, 55, 56, 57, 58, 59, 60, 61, 63, 64, 66, 67, 68 , 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 92, 93, 94, 95, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 12 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176 , 177, 178, 179, 180, 181, 182, 183, 184, 185, 186, 188, 189, 190, 193, 194, 195, 196, 197, 198, 199, 200.201, 202, 203, 20 4, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 232, 233, 234, 237, 238, 239, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 253, 254, 255, 256, 257, 258, 259 , 260, 261, 262, 263, 264, 265, 266, 267, 269, 270, 271, and 273 at 300 ppm showed over 75% control in these tests compared to untreated tests, which showed strong disease progression.

Example 2: Rhizoctonia solani (rice epidermal disease/potato black scab): The compound was diluted in 0.3% DMSO and then added to the potato glucose agar medium immediately prior to application to Petri dishes. 5 ml of the medium with compound at the desired concentration were dispensed into 60 mm sterile Petri dishes. After solidification, each dish was seeded with 5 mm mycelium discs taken from the outer edge of an actively growing hazardous culture plate. The plates were placed in growth chambers at 25° C. and 60% relative humidity for seven days and radial growth was measured. Connections 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 39, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 54, 55, 56, 57, 58, 59, 60, 61, 63, 66, 67, 68, 69, 70, 71 , 72, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 92, 93, 94, 95, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 127, 128, 129, 130, 131 , 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 151, 152, 153, 154, 155, 156, 157, 158, 1 59, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 178, 179, 180, 181, 182, 183, 184 185 186 189 191 193 196 197 198 199 200 201 204 205 206 207 208 209 210 211 212 213 214 215 21 6, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 232, 239, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 253, 254, 255, 256, 257, 258, 259, 261, 262, 263, 264, 265, 267, 269, 270, 271 and 273 and 33 at 300 ppm showed more than 80% control in such tests compared to untreated tests, which showed a strong development of the disease.

Example 3: Botrytis cinerea (gray mold): The compound was diluted in 0.3% DMSO and then added to the potato glucose agar medium just prior to application to Petri dishes. 5 ml of the medium with compound at the desired concentration were dispensed into 60 mm sterile Petri dishes. After solidification, each dish was seeded with 5 mm mycelium discs taken from the outer edge of an actively growing hazardous culture plate. The plates were placed in growth chambers at 22° C. and 90% relative humidity for seven days and radial growth was measured. Connections 1, 3, 4, 5, 6, 7, 8, 9, 10, 11, 13, 14, 15, 16, 17, 18, 21, 22, 23, 26, 27, 28, 29, 30, 32, 35, 37, 40, 41, 42, 43, 44 , 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 63, 65, 66, 67, 69, 70, 71, 74, 75, 76, 77, 78, 79, 80, 8 1, 82, 83, 84, 85, 86, 87, 88, 89, 92, 93, 94, 95, 97, 98, 99, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 113, 114, 116, 117, 118, 119, 120, 121, 123, 124, 128, 129, 130, 131, 132, 133. 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144 , 145, 146, 149, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 1 72 173 174 175 176 177 178 179 180 181 182 183 184 185 186 187 188 189 190 191 193 195 196 197 198 199, 200, 201, 204, 206, 207, 208, 209, 210, 211, 212, 213, 214, 217, 219, 220, 221, 222, 223, 224, 225, 230, 232, 233, 23 4, 235, 236, 238, 239, 242, 244, 245, 246, 247, 248, 249, 250, 251, 252, 253, 254, 255, 256, 257, 258, 259, 260, 261, 262, 263, 264, 265, 266, 267, 269, 270, 271, 272, and 273 at 300 ppm showed over 80% control in these tests compared to untreated tests, which showed strong disease progression.

Example 4: Alternaria solani (Tomato/Potato Alternaria): The compound was diluted in 0.3% DMSO and then added to potato-glucose agar medium immediately prior to application to Petri dishes. 5 ml of the medium with compound at the desired concentration were dispensed into 60 mm sterile Petri dishes. After solidification, each dish was seeded with 5 mm mycelium discs taken from the outer edge of an actively growing hazardous culture plate. The plates were placed in growth chambers at 25° C. and 60% relative humidity for seven days and radial growth was measured. Connections 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 37, 39, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 63, 66, 67, 68, 69 , 70, 71, 72, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102 , 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 1 27 128 129 130 131 132 133 134 135 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 17 6, 177, 178, 179, 180, 181, 182, 184, 185, 186, 195, 196, 197, 198, 199, 200, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 232, 233, 234, 237 , 238, 239, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 253, 254, 255, 256, 257, 258, 259, 260, 261, 262, 263, 2 64, 265, 266, 267, 269, 270, 271, 272, and 273 at 300 ppm showed over 75% control in these tests compared to untreated tests, which showed strong disease progression.

Example 5: Colletotrichum capsici (anthracnose): The compound was diluted in 0.3% DMSO and then added to potato glucose agar medium just prior to application to Petri dishes. 5 ml of the medium with compound at the desired concentration were dispensed into 60 mm sterile Petri dishes. After solidification, each dish was seeded with 5 mm mycelium discs taken from the outer edge of an actively growing hazardous culture plate. The plates were placed in growth chambers at 25° C. and 60% relative humidity for seven days and radial growth was measured. Connections 1, 3, 4, 5, 6, 7, 8, 9, 10, 11, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 25, 26, 27, 28, 29, 30, 32, 34, 35, 37, 39, 41 , 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 57, 58, 59, 60, 63, 66, 67, 69, 70, 71, 72, 74, 75, 76, 78, 79, 80, 8 1, 82, 83, 84, 85, 86, 87, 92, 93, 94, 95, 99, 100, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 1 16, 117, 118, 119, 120, 121, 122, 123, 124, 127, 128, 129, 130, 131, 132, 133. 134, 135, 136, 137, 138, 139, 140, 142, 143, 144, 145, 146, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 172, 173, 17 4, 175, 176, 177, 178, 179, 180, 184, 185, 186, 195, 196, 197, 198, 199, 200, 201, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 220, 221, 222, 223, 225, 239, 243, 245, 246, 249, 254, 255, 256, 257, 258, 259, 260, 261, 262, 263 , 269, and 270 at 300 ppm showed over 80% control in these tests compared to untreated tests, which showed strong disease progression.

Example 6: Septoria lycopersici (tomato leaf spot): The compound was diluted in 0.3% DMSO and then added to the potato glucose agar medium just prior to application to Petri dishes. 5 ml of the medium with compound at the desired concentration were dispensed into 60 mm sterile Petri dishes. After solidification, each dish was seeded with 5 mm mycelium discs taken from the outer edge of an actively growing hazardous culture plate. The plates were placed in growth chambers at 25° C. and 70% relative humidity for seven days and radial growth was measured. Connections 1, 3, 4, 5, 6, 7, 8, 9, 13, 14, 15, 16, 17, 18, 20, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 37, 41, 42 , 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 63, 64, 66, 67, 68, 69, 70, 71, 72, 74, 81, 82, 8 3, 84, 86, 92, 93, 94, 102, 104, 105, 106, 108, 109, 110, 111, 112, 113, 114, 116, 117, 118, 128, 129, 130, 131, 133. 134, 135, 138, 139, 142, 143, 144, 145, 146, 154, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 172 , 173, 174, 175, 176, 177, 178, 185, 186, 195, 196, 197, 198, 199, 200,201, 206, 207, 208, 209, 210, 211, 212, 213, 214, 21 5, 216, 220, 221, 222, 223, 224, 225, 228, 229, 243, 244, 245, 246, 248, 249, 250, 252, 254, 255, 256, 257, 258, 259, 260, 261, 262, 263, 270 and 271 at 300 ppm showed over 70% control in these tests compared to untreated tests which showed strong disease progression.

Example 7: Fusarium culmorum (cereal late blight): The compound was diluted in 0.3% DMSO and then added to potato glucose agar medium just prior to application to Petri dishes. 5 ml of the medium with compound at the desired concentration were dispensed into 60 mm sterile Petri dishes. After solidification, each dish was seeded with 5 mm mycelium discs taken from the outer edge of an actively growing hazardous culture plate. The plates were placed in growth chambers at 25° C. and 60% relative humidity for seven days and radial growth was measured. Connections 1, 4, 5, 6, 7, 9, 11, 14, 15, 16, 17, 18, 22, 23, 26, 27, 28, 29, 30, 31, 32, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 63, 66, 67, 68, 69, 70, 71, 72, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 87, 92, 93, 94, 99, 104, 105, 108, 109, 110, 111, 112, 113, 114, 117, 118, 119, 120, 121, 129, 132, 136, 137, 138, 139, 142, 143, 144, 145, 146, 153, 154, 155, 156, 157, 158, 159, 160, 161, 162, 165, 167, 169, 170, 171, 172, 173, 174, 175, 176, 178, 179 , 180, 181, 185, 186, 189, 196, 197, 198, 199, 200, 201, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 220, 221, 222, 2 23, 224, 225, 239, 249, 250, 252, 253, 256, 257, 258, 259, 260, 261, 262, 263, 269, and 271 at 300 ppm showed over 75% control in such tests compared to untreated tests, which showed strong disease progression.

Examples of biological tests (GREENHOUSE)

Example A Testing Rice for Pyricularia oryzae

The compound was diluted in 2% DMSO/acetone and then mixed with water to calibrate the 50 ml spray volume. This 50 ml spray solution was filled into spray bottles for future use.

To test the preventive effect of the compounds, healthy young seedlings of rice/plant grown in a greenhouse were sprayed with a solution of the active compound at the indicated application rate inside the spray chambers using wide spray tips. One day after treatment, the plants were infected with a spore suspension (sterile water) containing an inoculum of 1.4×10 ⁶ Pyricularia oryzae. The infected plants were then placed in a greenhouse chamber at 24° C. and 95% relative humidity for disease manifestation.

A visual assessment of the activity of the compound was carried out by assessing the severity of the disease (scale 0-100%) on the treated plants at 3, 7, 10 and 15 days after application. Efficacy (% control) of the compounds was calculated by comparing the disease score in the treated group with the control untreated group. For plants sprayed with the compounds, the phytotoxic effects of the compound were also evaluated by recording symptoms such as necrosis, chlorosis and stunting. Compounds 26, 44, 48, 51, 63, 87, 93, 94, 96, 103, 110, 112, 120, 133, 135, 148, 149 and 183 at 500 ppm showed 70-100% control in such tests compared to untreated tests which showed strong disease progression. None of the compounds showed phytotoxicity for rice crops.

Example B: Testing wheat for Fusarium culmorum

The compound was diluted in 2% DMSO/acetone and then mixed with water to calibrate the 50 ml spray volume. This 50 ml spray solution was filled into spray bottles for future use.

To test the preventive effect of the compounds, healthy young wheat grown in a greenhouse was sprayed with a solution of the active compound at the indicated application rate inside the spray chambers using wide spray tips. One day after treatment, the plants were infected with a spore suspension (2% rye malt) containing an inoculum of 2×10 ⁶ Fusarium culmorum. Then the infected plants were placed in a greenhouse chamber at a temperature of 24°C and a relative humidity of 80-90% for the manifestation of the disease.

A visual assessment of the activity of the compound was carried out by assessing the severity of the disease (scale 0-100%) on the treated plants at 3, 7, 10 and 15 days after application. The efficacy (% control) of the compounds was assessed by comparing the disease score in the treated group with the control untreated group. For plants sprayed with the compounds, the phytotoxic effects of the compound were also evaluated by recording symptoms such as necrosis, chlorosis and stunting. Connections 1, 7, 12, 13, 16, 17, 18, 19, 22, 23, 28, 30, 32, 33, 35, 41, 42, 57, 75, 76, 77, 81, 96, 101, 136, 149, 157, 160 172 and 183 at 500 ppm showed 70-100% control in such tests compared to untreated tests which showed strong disease progression. None of the compounds showed phytotoxicity to wheat.

Example C: Testing tomatoes for Botrytis cinera

The compound was diluted in 2% DMSO/acetone and then mixed with water to calibrate the 50 ml spray volume. This 50 ml spray solution was filled into spray bottles for future use.

To test the preventive effect of the compounds, healthy young bean/chili plants grown in a greenhouse were sprayed with a solution of the active compound at the indicated application rate inside the spray chambers using wide spray tips. One day after treatment, the plants were infected with a spore suspension (2% rye malt) containing an inoculum of 1.2×10 ⁶ Botrytis cinera. Then the infected plants were placed in a greenhouse chamber at a temperature of 18-20°C and a relative humidity of 90-100% for the manifestation of the disease.

A visual assessment of the activity of the compound was carried out by assessing the severity of the disease (scale 0-100%) on the treated plants at 3, 7, 10 and 15 days after application. The efficacy (% control) of the compounds was assessed by comparing the disease score in the treated group with the control untreated group. For plants sprayed with the compounds, the phytotoxic effects of the compound were also evaluated by recording symptoms such as necrosis, chlorosis and stunting. Connections 1, 2, 3, 4, 5, 6, 7, 9, 10, 11, 12, 13, 14, 15, 17, 18, 19, 22, 23, 24, 25, 27, 28, 29, 31, 32, 40, 43, 59, 90, 94, 10 1, 102, 103, 104, 105, 133, 166, 170, 179, 180 and 184 at 500 ppm showed 70-100% control in such tests compared to untreated tests which showed severe disease progression. None of the compounds showed phytotoxicity in tomatoes.

Example D: Testing tomatoes for Alternaria solani

The compound was diluted in 2% DMSO/acetone and then mixed with water to calibrate the 50 ml spray volume. This 50 ml spray solution was filled into spray bottles for future use.

To test the preventive effect of the compounds, healthy young tomato plants grown in a greenhouse were sprayed with a solution of the active compound at the indicated application rate inside the spray chambers using wide spray tips. One day after treatment, the plants were infected with a spore suspension (2% rye malt) containing an inoculum of 0.24×10 ⁶ Alternaria solani. Then the infected plants were placed in a greenhouse chamber at a temperature of 22-24°C and a relative humidity of 90-95% for the manifestation of the disease.

A visual assessment of the activity of the compound was carried out by assessing the severity of the disease (scale 0-100%) on the treated plants at 3, 7, 10 and 15 days after application. The efficacy (% control) of the compounds was assessed by comparing the disease score in the treated group with the control untreated group. For plants sprayed with the compounds, the phytotoxic effects of the compound were also evaluated by recording symptoms such as necrosis, chlorosis and stunting. Connections 2, 8, 9, 23, 25, 27, 29, 31, 32, 35, 36, 40, 41, 42, 48, 50, 68, 71, 97, 115, 128, 160, 161, 170, 174, 175, 176, 178, 179, 180 and 180 at 500 ppm showed 70-100% control in these tests compared to untreated tests which showed strong disease progression. None of the compounds showed phytotoxicity for tomatoes.

The table below shows a comparative analysis of the compound claimed in the prior art (WO200046184) and the compound specified in this invention.

From the above comparison and analysis, it can be concluded that the compounds of this invention show an unexpectedly high biological activity for the tested pathogens in comparison with the biological activity of the reference compound.

Once the invention has been described with respect to certain preferred aspects, other aspects will become apparent to those skilled in the art upon examination of the specifications. It will be apparent to those skilled in the art that many modifications to materials and methods can be practiced without departing from the scope of the invention.

Claims (294)

1. Compound of formula (I) Where R ¹ represents hydrogen; R ² represents C _2-8 -alkyl; R ³ represents C _1-6 alkyl; wherein each R ² and R ³ may be optionally substituted with one or more groups selected from the group consisting of X and R'; R ⁴ , R ⁵ , R ⁶ and R ⁷ are independently selected from the group consisting of hydrogen, X, CN, S(O) _n R'', OR'', C _1-8 -alkyl and C _3-8 -cycloalkyl; and all of the groups mentioned above may be optionally replaced by one or more groups selected from the group consisting of X and R'; R ⁸ and R ⁹ are independently selected from the group consisting of hydrogen, X, CN, (C=O)-R'', C _1-6 -alkyl and C _1-6 -alkoxy; and all the groups specified above may be replaced by one or more groups selected from the group consisting of X and R' or R ⁸ and R ⁹ , together with the atoms to which they are attached, can form the group =C(R'R'''), =NR'''; A is selected from the group consisting of fused or unfused C _6-10 -aryl and pyridinyl; said ring A is optionally replaced by one or more R ¹⁰ groups; Where R ¹⁰ is selected from the group containing hydrogen, X, CN, NO ₂ , NR' ₂ , S(O) _n R'', C _1-8 -alkyl, C _1-8 -haloalkyl, C _1-8 -alkoxy, C _1-8 -alkylthio, C _1-8 -haloalkoxy, C _1-8 -haloalkylthio, C _3-8 -cycloalkyl; and wherein each R ⁸ , R ⁹ and R ¹⁰ may be optionally substituted with one or more groups selected from the group consisting of X and R'; Where X represents halogen; R' is selected from the groups consisting of hydrogen, straight or branched chain C _1-6 alkyl and cyclic C _3-6 alkyl, wherein each R' group is optionally substituted with one or more X's; R'' is selected from the groups consisting of hydrogen, NR' ₂ , OR' and straight or branched chain C _1-12 alkyl; each R'' group is optionally substituted by one or more groups selected from the group consisting of X, R', OR', CN and phenyl, which is optionally substituted by one or more R'; R''' is selected from the groups consisting of hydrogen and straight or branched chain C _1-6 alkyl; and all groups mentioned above may be substituted by one or more X; m and n represent integers, where n=0, 1 or 2; and m=1 or 2; and agronomically acceptable salts of said compounds. 2. A compound of formula (I) according to claim 1, wherein each substituent is independently selected from: R ¹ - hydrogen; R ² - ethyl; R ³ - methyl; R ⁴ and R ⁵ are independently selected from the group consisting of X, CN, S(O) _n R'', C _1-6 alkyl and C _3-8 cycloalkyl; R ⁶ and R ⁷ are independently selected from the group consisting of hydrogen, X, C _1-6 alkyl and C _3-8 cycloalkyl; R ⁸ and R ⁹ are selected from the group containing hydrogen, X, CN, (C=O)-R'', C _1-4 -alkoxy; A is phenyl; wherein said phenyl ring is optionally substituted with one or more R ¹⁰ groups; R ¹⁰ - X, CN, NO ₂ , NR' ₂ , S(O) _n R'', C _1-6 -haloalkyl, C _1-6 -alkoxy, C _1-6 -alkylthio, C _1-6 -haloalkoxy , C _1-6 -haloalkylthio, C _3-8 -cycloalkyl; and agronomically acceptable salts of said compounds. 3. A compound of formula (I) according to claim 1 or 2, wherein each substituent is independently selected from: R ¹ - hydrogen; R ² - C _2-6 -alkyl; R ³ - methyl; R ⁴ and R ⁵ are selected from the group consisting of X, CN, S(O) _n R'', C _1-6 -alkyl, C _1-6 -haloalkyl and C _3-8 -cycloalkyl; R ⁶ and R ⁷ are selected from the group containing hydrogen, X and C _1-6 -alkyl; R ⁸ and R ⁹ are selected from the group containing hydrogen, X, C _1-4 -alkyl, C _1-4 -alkoxy; R ¹⁰ is selected from the group consisting of X, CN, C _1-6 -alkyl, C _1-6 -alkoxy, C _1-6 -alkylthio, C _1-6 -haloalkoxy and C _3-8 -cycloalkyl; and agronomically acceptable salts of said compounds. 4. Connection according to any one of paragraphs. 1-3, where the compound of formula (I) is: N'-(4-benzyl-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(4-(methoxy(phenyl)methyl)-2,5-dimethylphenyl)-N-methylformimidamide; N'-(4-(3,5-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(4-bromobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(3,4-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(4-(4-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-(4-(methylthio)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-bromo-4-(4-bromobenzyl)-3,6-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(3-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-(4-(methylsulfonyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(4-(3-bromobenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(3-bromobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide; N'-(2-chloro-4-(2-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(2-chlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-(4-(methylsulfonyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(3,4-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(3,5-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(4-bromobenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-(2-(methylthio)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-(2-(methylsulfonyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-(2-(methylsulfonyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(4-(2,5-dimethylbenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(3-chloro-4-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(4-(3-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide; N'-(2-chloro-4-(3-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-((Z)-(methylimino)(phenyl)methyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-5-methyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-5-methyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(4-(3-methoxybenzyl)-2,5-dimethylphenyl)-N-methylformimidamide; N'-(2,5-dimethyl-4-(3-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(4-(3-cyanobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(4-cyanobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-(3-nitrobenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-(2-nitrobenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-(3-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(4-(3-fluoro-5-(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-methylformimidamide; N'-(2,5-dimethyl-4-(2-methyl-5-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(4-(4-methoxybenzyl)-2,5-dimethylphenyl)-N-methylformimidamide; N-ethyl-N'-(4-(4-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide; N'-(2-chloro-4-(4-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(4-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(3-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-5-methyl-4-(3-nitrobenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(3-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(difluoro(phenyl)methyl)-2-iodo-3,6-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-benzyl-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-5-methyl-4-(2-nitrobenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(4-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-5-methyl-4-(4-((trifluoromethyl)thio)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(3-chlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(4-chlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-5-methyl-4-(3-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-isopropyl-N-methylformimidamide; N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-isopropyl-N-methylformimidamide; N-(cyclopropylmethyl)-N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide; N-(cyclopropylmethyl)-N'-(4-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-isopropylformimidamide; N'-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-(cyclopropylmethyl)-N-isopropylformimidamide; N'-(2,5-dimethyl-4-(4-((trifluoromethyl)thio)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-(2-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-(4-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(4-chloro-3-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(3,5-bis(trifluoromethyl)benzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(2-chloro-4-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(2-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-5-methyl-4-(4-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-5-methyl-4-(2-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-5-methyl-4-(2-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-(4-methyl-3-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(4-(4-chloro-3-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(3,5-bis(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(3-(1-cyanoethyl)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(4-chloro-3-methylbenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(4-(4-fluoro-3-methylbenzyl)-2,5-dimethylphenyl)-N-methylformimidamide; N'-(4-(2-chloro-4-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(3-(dimethiamino)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(2,3-dimethylbenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(3,4-dimethylbenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N-(4-(3,5-dimethylbenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(2-cyanobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-(2-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dimethyl-4-(4-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(4-(3-chloro-2-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(4-fluoro-3-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(4-chloro-3-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-5-methyl-4-(4-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-5-methyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(3-chloro-2-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-5-methyl-4-(3-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(2-chloro-3-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(3-chloro-2-fluoro-5-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(cyano(phenyl)methyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(2,3-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(3,5-difluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(3,5-dimethylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(2-chloro-3-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(3,5-difluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(2,3-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(3-chloro-2-fluoro-5-(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(3-chloro-5-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(4-chloro-3-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(3-fluoro-4-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(3,4-difluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(3-fluoro-4-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(3-fluoro-5-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dichloro-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(4-(4-chloro-3-(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(2-chloro-5-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(4-(3-fluoro-4-methylbenzyl)-2,5-dimethylphenyl)-N-methylformimidamide; N'-(4-(4-chloro-3-(trifluoromethoxy)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(3,4-difluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dichloro-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dichloro-4-(3-fluorobenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dichloro-4-(2-fluorobenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dichloro-4-(2-chlorobenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dichloro-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dichloro-4-(3-chlorobenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(4-(2,6-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(2-bromobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(2-chloro-6-fluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(4-(3-fluoro-5-methoxybenzyl)-2,5-dimethylphenyl)-N-methylformimidamide; N-ethyl-N'-(4-(5-fluoro-2-methylbenzyl)-2,5-dimethylphenyl)-N-methylformimidamide; N-ethyl-N'-(4-(3-fluoro-4-(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-methylformimidamide; N'-(4-(2-chloro-5-(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(2,5-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(2,4-difluorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(2,4-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(4-(2-fluorobenzyl)phenyl)-N-methylformimidamide; N'-(4-(2-chlorobenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(5-fluoro-2-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(2,5-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(4-fluoro-2-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(2-chloro-5-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(3-fluoro-5-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(2,3-dimethylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(5-fluoro-2-methyl-4-(3-methylbenzyl)phenyl)-N-methylformimidamide; N-ethyl-N'-(5-fluoro-4-(3-fluorobenzyl)-2-methylphenyl)-N-methylformimidamide; N'-(4-(3-chlorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(2-chlorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(5-fluoro-2-methyl-4-(4-methylbenzyl)phenyl)-N-methylformimidamide; N'-(2-chloro-4-(3-chloro-5-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(4-chloro-3-(trifluoromethoxy)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(2-chloro-5-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(2,4-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(2,4-difluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(4-fluoro-3-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dichloro-4-(3-(tritoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-dichloro-4-(3-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(2-chloro-6-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(5-fluoro-4-(2-fluorobenzyl)-2-methylphenyl)-N-methylformimidamide; N-ethyl-N'-(5-fluoro-2-methyl-4-(2-methylbenzyl)phenyl)-N-methylformimidamide; N'-(2-chloro-4-(cyano(4-(trifluoromethyl)phenyl)methyl)-5-methylphenyl)-N-ethylmethylformimidamide; N'-(2-chloro-4-(cyano(3-(trifluoromethyl)phenyl)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(cyano(4-fluorophenyl)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-((3-chloro-4-fluorophenyl)(cyano)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(cyano(p-tolyl)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-((2-chlorophenyl)(cyano)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-((4-chlorophenyl)(cyano)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(cyano(3-fluorophenyl)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(2,6-dichlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(5-fluoro-2-methyl-4-(3-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide; N'-(2-cyclopropyl-4-(3-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-cyclopropyl-5-methyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(4-(3-chlorobenzyl)-2-cyclopropyl-5-methylphenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(4-(3-fluoro-5-methylbenzyl)-2,5-dimethylphenyl)-N-methylformimidamide; N-ethyl-N'-(4-(2-fluoro-4-(trifluoromethyl)benzyl)-2,5-dimethylphenyl)-N-methylformimidamide; N'-(2,5-dimethyl-4-(pyridin-2-ylmethyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(2,6-difluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-5-methyl-4-(pyridin-3-ylmethyl)phenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(2-fluoro-5-methyl-4-(3-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide; N-ethyl-N'-(2-fluoro-5-methyl-4-(3-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide; N-ethyl-N'-(2-fluoro-5-methyl-4-(2-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide; N'-(4-(3-chlorobenzyl)-2-fluoro-5-methylphenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(2-fluoro-4-(3-fluorobenzyl)-5-methylphenyl)-N-methylformimidamide; N-ethyl-N'-(2-fluoro-5-methyl-4-(3-methylbenzyl)phenyl)-N-methylformimidamide; N-ethyl-N'-(2-fluoro-5-methyl-4-(4-methylbenzyl)phenyl)-N-methylformimidamide; N-ethyl-N'-(2-fluoro-5-methyl-4-(2-methylbenzyl)phenyl)-N-methylformimidamide; N'-(4-(2-chlorobenzyl)-2-fluoro-5-methylphenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(2-fluoro-4-(2-fluorobenzyl)-5-methylphenyl)-N-methylformimidamide; N'-(2,5-dimethyl-4-((Z)-(methylimino)(o-tolyl)methyl)phenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(4-(3-fluorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-methylformimidamide; N'-(4-(3-chlorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-bromo-3,6-dimethyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(2-fluoro-6-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-cyclopropyl-4-(2-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N-(2-cyclopropyl-5-methyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(4-(2-chlorobenzyl)-2-cyclopropyl-5-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-cyclopropyl-5-methyl-4-(3-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(2-fluoro-4-(4-methylbenzyl)-5-(trifluoromethyl)phenyl)-N-methylformimidamide; N'-(4-(2-chlorobenzyl)-2-fluoro-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(2-fluoro-4-(2-fluorobenzyl)-5-(trifluoromethyl)phenyl)-N-methylformimidamide; N-ethyl-N'-(2-fluoro-4-(2-methylbenzyl)-5-(trifluoromethyl)phenyl)-N-methylformimidamide; N'-(4-(3-chlorobenzyl)-2-fluoro-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N'-(2-fluoro-4-(3-fluorobenzyl)-5-(trifluoromethyl)phenyl)-N-methylformimidamide; N-ethyl-N'-(2-fluoro-4-(3-methylbenzyl)-5-(trifluoromethyl)phenyl)-N-methylformimidamide; N-ethyl-N'-(2-fluoro-5-(trifluoromethyl)-4-(3-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide; N-ethyl-N'-(2-fluoro-4-(3-(trifluoromethoxy)benzyl)-5-(trifluoromethyl)phenyl)-N-methylformimidamide; N-ethyl-N-methyl-N'-(5-methyl-4-(2-methylbenzyl)-2-(methylsulfonyl)phenyl)formimidamide; N-ethyl-N-methyl-N'-(5-methyl-4-(4-methylbenzyl)-2-(methylsulfonyl)phenyl)formimidamide; N'-(5-chloro-4-(cyano(5-fluoro-2-methylphenyl)methyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide; methyl 2-(2-chloro-4-(((ethyl(methyl)amino)methylene)amino)-5-methylphenyl)-2-(3-chlorophenyl)acetate; N'-(4-(1-(4-bromophenyl)vinyl)-5-chloro-2-methylphenyl)-N-ethyl-N-methylformimidamide; 2-(2-chloro-4-(((ethyl(methyl)amino)methylene)amino)-5-methylphenyl)-2-(3-fluorophenyl)-N,N-dimethylpropanamide; 2-(2-chloro-4-(((ethyl(methyl)amino)methylene)amino)-5-methylphenyl)-2-(5-fluoro-2-methylphenyl)-N,N-dimethylacetamide; N'-(5-chloro-4-((4-chloro-3-fluorophenyl)(cyano)methyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-difluoro-4-(2-fluorobenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(4-(3-chlorobenzyl)-2,5-difluorophenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-difluoro-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-difluoro-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(4-(2-chlorobenzyl)-5-cyano-2-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(5-cyano-4-(2-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(5-cyano-2-methyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(4-(3-chlorobenzyl)-5-cyano-2-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(5-cyano-4-(3-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(5-cyano-2-methyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(5-cyano-2-methyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(4-(2-chlorobenzyl)-2,5-difluorophenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-difluoro-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(5-chloro-4-(2-chlorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(5-chloro-4-(2-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(5-chloro-2-methyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(5-chloro-4-(3-chlorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(5-chloro-4-(3-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(5-chloro-2-methyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(5-chloro-2-methyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(4-(2-chlorobenzyl)-2-cyclopropyl-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-cyclopropyl-4-(3-methylbenzyl)-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-cyclopropyl-4-(4-methylbenzyl)-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(4-(3-chlorobenzyl)-2-cyclopropyl-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-cyclopropyl-4-(3-fluorobenzyl)-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-cyclopropyl-4-(4-cyclopropylbenzyl)-3,6-dimethylphenyl)-N-ethyl-N-methylformimidamide; N'-(2-cyclopropyl-4-(2-methylbenzyl)-5-(trifluoromethyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2,5-difluoro-4-(3-fluorobenzyl)phenyl)-N-ethyl-N-methylformimidamide; N'-(2-chloro-4-(cyano(3-(trifluoromethyl)phenyl)methyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N-methyl-N'-(5-methyl-4-(3-methylbenzyl)-2-(methylsulfonyl)phenyl)formimidamide; N-ethyl-N'-(4-(2-fluorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-methylformimidamide; N'-(4-(2-chlorobenzyl)-5-methyl-2-(methylsulfonyl)phenyl)-N-ethyl-N-methylformimidamide; N-ethyl-N-methyl-N'-(5-methyl-2-(methylsulfonyl)-4-(3-(trifluoromethyl)benzyl)phenyl)formimidamide; N-ethyl-N-methyl-N'-(5-methyl-2-(methylsulfonyl)-4-(3-(trifluoromethoxy)benzyl)phenyl)formimidamide; N-ethyl-N'-(5-fluoro-2-methyl-4-(3-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide; and agronomically acceptable salts of said compounds. 5. A composition for the control or prevention of infection of beneficial plants caused by phytopathogenic fungi, consisting of a compound of formula (I) according to claim 1 and one or more inert carriers, in which the concentration of the compound of formula (I) varies from 1 to 90% by weight relative to total mass of the composition. 6. The composition according to claim 5, further containing one or more active compatible compounds selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and/or mixtures thereof. 7. The composition according to claim 5, in which the concentration of the compound of formula (I) varies from 5 to 50% by weight relative to the total weight of the composition. 8. Use of a compound of formula (I) according to claim 1 for the control or prevention of infection caused by phytopathogenic fungi in agricultural crops and/or horticultural crops. 9. Use of the composition according to claim 5 for the control or prevention of infection caused by phytopathogenic fungi of agricultural crops and/or horticultural crops. 10. Use of a compound of formula (I) according to claim 1 or a composition according to claim 5 for the control or prevention of infection caused by phytopathogenic fungi of agricultural crops, where the agricultural crops are cereals, wheat, rice, soybeans and other legumes, fruits and fruits trees, nuts and walnut trees, citrus and citrus trees, any garden plants, pumpkins, oilseeds, tobacco, coffee, tea, cocoa, sugar beets, sugar cane, cotton, potatoes, tomatoes, onions, peppers and other vegetables and ornamental plants . 11. A method for controlling or preventing infection of beneficial plants by phytopathogenic fungi in agricultural crops and/or horticultural crops, wherein the compound of formula (I) according to claim 1 or the composition according to claim 5 is applied to the plant, part of the plant or locus. 12. A method for controlling or preventing infection of beneficial plants by phytopathogenic fungi in agricultural crops and/or horticultural crops, wherein the compound of formula (I) according to claim 1 or the composition according to claim 5 is applied to the seeds of the plant. 13. A method for controlling or preventing infection of beneficial plants by phytopathogenic fungi in agricultural crops and/or horticultural crops using a compound of formula (I) according to claim 1 or a composition according to claim 5, which includes applying an effective dose of the compound or composition in an amount of 1 g up to 5 kg per hectare of agricultural or horticultural crops.