4-Substituted phenylamine derivatives and their use for protecting crops by combating unwanted phytopathogenic microorganisms - Patents.com

Abstract

The present invention relates to 4-substituted phenylamine derivatives of general formula (I), wherein R 1 ~R 9 and A have the meanings as defined in the specification. The present invention further relates to processes for their preparation and the use of said compounds for combating unwanted phytopathogenic microorganisms, as well as agents comprising the phenylamine derivatives for said purpose, all according to the invention. The present invention further relates to a method for combating unwanted pathogenic microorganisms by applying the 4-substituted phenylamine derivatives of general formula (I) to such unwanted microorganisms and / or their habitats, in accordance with the present invention. [Formula 1] (I) [Selection diagram] None

Description

[Technical field]

[0001] The present invention relates to compounds intended to protect crops by combating unwanted phytopathogenic microorganisms. More precisely, the subject of the present invention relates to 4-substituted phenylamine derivatives used to protect crops by combating unwanted phytopathogenic microorganisms. [Background technology]

[0002] Controlling damage to crops caused by phytopathogenic microorganisms is crucial to achieving high crop efficiency. For example, damage caused by plant diseases to ornamental plants, vegetables, field crops, cereals and fruit crops can lead to significant loss of productivity, which can lead to increased costs for consumers. Many products for controlling such damage are available on the market. There is still a need for new compounds that are more effective, less expensive, less toxic, safer to the environment, and / or have different modes of action. Certain phenylamine derivatives have been disclosed in the literature as antibacterial active ingredients in pest control agents. For example, WO2000046184, WO2003093224, WO2003024219, WO2005089547, WO2005120234 and US20110082036 disclose the use of phenylamine derivatives, especially phenylamidines, as fungicides, alone or as part of a composition. Certain phenylbenzamide compounds, methods for producing such compounds, and their use for controlling undesirable microorganisms are disclosed in WO2004005242.

[0003] US4173637 discloses phenylurea compounds and compositions containing the compounds as insecticides. JP08291146 discloses N-substituted phenylsulfonamide compounds with excellent herbicidal activity, especially herbicides for paddy fields. WO2008110314 discloses fluoroalkylphenylamidines as fungicidal compounds, methods for preparing the same, and methods for protecting seeds from undesirable microorganisms using such compounds. One other PCT publication WO2011095462 discloses carboxamide-containing phenylamine derivatives, methods for preparing the same, and insecticidal, acaricidal, molluscicidal or molluscicidal compositions containing the same. Certain pharmaceutically useful amidine compounds exhibiting antifungal activity against pathogenic fungi, including fungi of the genera Candida, Aspergillus and Trichophyton, are disclosed in WO2013018735.

[0004] Although the effectiveness of phenylamine derivatives described in the prior art is good, they leave something to be desired in various cases.Therefore, there is always a high interest in using new pest control compounds in agriculture to avoid and / or control the occurrence of microorganisms such as fungal or bacterial pathogens or pests that are resistant to known active ingredients.Therefore, there is a high interest in using new compounds that are more active than those already known, with the aim of reducing the amount of active compounds used and at the same time maintaining at least the same effectiveness as those already known.

[0005] We have now found a new family of compounds with the above-mentioned effects or advantages. Thus, the new family of compounds according to the present invention, namely 4-substituted phenylamine derivatives substituted at the phenyl ring, allows unexpected and much higher activity against undesirable microorganisms such as fungal or bacterial pathogens or pests. Summary of the Invention [Means for solving the problem]

[0006] The present invention relates to a compound represented by the general formula (I)

[0007] [ka] With regard to the novel inventive 4-substituted phenylamine derivatives of the formula:

[0008] The 4-substituted phenylamine derivatives of the present invention are novel and inventive in view of US8080688 and its corresponding EP application no. 2120558.

[0009] US8080688 is a general formula

[0010] [ka] US Pat. No. 5,993,336 discloses 3,4-disubstituted phenoxyphenyl amidines represented by the formula:

[0011] See Scheme I, steps (a-f) on pages 18-25 of Compound (I) and steps (g-j) on pages 27-30 of Compound (I) of US8080688. Also see the examples in Table IV on pages 48-49.

[0012] However, in the embodiments and claim 4 of paragraph 5 on page 18, the applicant of US8080688 discloses 3,4-disubstituted benzylphenylamidines. A list of 3,4-disubstituted benzylphenylamidine compounds disclosed in US8080688 is reproduced below: 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-propylimido-formamide, 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-ylmethylphenyl]-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-chloro-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-cyclopentyl-4-(trifluoromethyl)benzyl]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide.

[0013] The disclosure of this 3,4-disubstituted benzylphenylamidine compound in US8080688 is erroneous and unintentional for the following reasons: i) from the language of claim 4, it appears that the applicant intended to claim 3,4-disubstituted phenoxyphenylamidines and not 3,4-disubstituted benzylphenylamidines; ii) 3,4-disubstituted benzylphenylamidines cannot be prepared by the procedures described in the schemes and examples; iii) in Table IV on pages 48-49 of US8080688, only 3,4-disubstituted phenoxyphenylamidines are disclosed.

[0014] Therefore, in view of this typographical error requiring correction in US8080688 and its corresponding EP application no. 2120558, the compounds of the present invention are novel.

[0015] The inventiveness / unobviousness of the compounds of the present invention can be confirmed from the comparative results shown in the Examples section, where it is surprisingly observed that the compounds of the present invention further increase the effectiveness of crop protection against attack by pests, microorganisms, weeds or abiotic stresses. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0016] Thus, the present invention relates to a compound of general formula (I)

[0017] [ka] (In the formula, R 1 is 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 -Haloalkynyl, C 3~8 -Cycloalkyl, C 4~8 -Cycloalkenyl, C 5~8 -cycloalkynyl; in the cyclic ring system, one or more carbon atoms are selected from the group consisting of N, O, and S(O)nN, O, and S(O) n may be replaced by a heteroatom selected from the group consisting of: R 2 and R 3 are independently 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, C5~8 -Cycloalkynyl, C 5~18 -aryl, C 7~19 -Aralkyl, C 7~19 -alkaryl; in the cyclic ring system, one or more carbon atoms are selected from the group consisting of N, O, and (O) n or R 1 and R 2 , R 2 and R 3 Or R 1 and R 3 together with the atom to which they are attached or together with a further atom selected from the group consisting of C, N, O, S, as well as C(=O), C(=S), S(O) m and SiR'2 to form a 4-7 membered ring, which may be partially substituted by one or more of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; R 1 , R 2 and R 3 each of which 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; R 4 , R 5 , R 6 and R 7 are independently hydrogen, X, CN, SCN, SF5, S(O) n R'', SiR' 3、 OR'', NR'R'', (C=O)-R'', CR'=NR'', 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 1~12 -Haloalkoxy, C 1~12 -Haloalkylthio, C 3~8 -Cycloalkyl, C4~8 -Cycloalkenyl, C 5~8 -Cycloalkynyl, C 3~8 -Cycloalkyloxy, C 3~8 -Cycloalkylthio, C 5~18 -aryl, C 7~19 -Aralkyl, C 7~19 -alkaryl; in the cyclic ring system, one or more carbon atoms are selected from the group consisting of N, O, and S(O) n all of the above groups 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 R 4 and R 7 Or R 5 and R 6 together with the atom to which they are attached or together with a further atom selected from the group consisting of C, N, O, S, as well as C(=O), C(=S), S(O) m and SiR'2 to form a 4-7 membered ring, which may be partially substituted by one or more of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; R 4 , R 5 , R 6 and R 7 each of which 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; R 8 and R 9 are independently hydrogen, 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 -Alkyl, C 2~12 -Alkenyl, C2~12 -Alkynyl, C 1~12 -Alkoxy C 1~12 -Haloalkyl, C 2~12 -Haloalkenyl, C 2~12 -Haloalkynyl, C 1~12 -Haloalkoxy, C 1~12 -Haloalkylthio, C 3~8 -Cycloalkyl, C 4~8 -Cycloalkenyl, C 5~8 -Cycloalkynyl, C 3~8 -Cycloalkyloxy, C 3~8 -Cycloalkylthio, C 5~18 -aryl, C 7~19 -Aralkyl, C 7~19 -alkaryl; in the cyclic ring system, one or more carbon atoms are selected from the group consisting of N, O, and S(O) n any of the above groups 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 8 and R 9 together with the atom to which they are attached or together with a further atom selected from the group consisting of C, N, O, S, as well as C(=O), C(=S), S(O) m and SiR'2 to form a 3-7 membered ring, which may be optionally substituted in part by one or more of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; or R 8 and R 9 may together with the atom to which they are attached form a =C(R'R''), =S, =NR''' group; A is a condensed or non-condensed C 6~18 -aryl, C 5~18 -heteroaryl, wherein one or more carbon atoms are replaced by a heteroatom selected from N, O, S, and R10 C(=O), C(=S), S(O) optionally substituted with one or more groups m and SiR'2, with the proviso that heteroaryl does not represent thiazolyl or thiadiazolyl; R 10 are hydrogen, X, CN, SCN, SF5, R'', OR'', NO2, NR''2, SiR'3, (C=O)-R'', S(O) n R'', OS(O) n R'', NR'S(O) n R'', OSiR'3,C 1~8 -Alkyl-S(O) n R'', C 1~8 -Alkyl-(C=O)-R'', CR'=NR'', S(O) n C 5~18 -aryl, S(O) n C 7~19 -Aralkyl, S(O) n C 7~19 -Alkaril, 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 1~12 -Alkoxy, C 1~12 -Alkylthio, C 1~12 -Haloalkoxy, C 1~12 -Haloalkylthio, C 3~12 -Cycloalkyl, C 4~8 -Cycloalkenyl, C 5~8 -Cycloalkynyl, C 3~8 -Cycloalkyloxy, C 3~8 -Cycloalkylthio, C 7~19 -Aralkyl, C 7~19 -Alkaryl; Bicyclic C 5~12 -Alkyl, C 7~12 -alkenyl; in the cyclic ring system, one or more carbon atoms are selected from the group consisting of N, O, and S(O) nany of the above groups 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; R 8 , R 9 , and R 10 each of which 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; X represents a halogen; R' is a straight or branched chain C optionally substituted with hydrogen or one or more X's. 1~12 -Alkyl or cyclic C 3~10 - represents alkyl; R″ is a straight or branched chain C optionally substituted with one or more groups selected from the group consisting of hydrogen; NR′2, OR′, X, R′, OR′, SR′, NR′2, SiR′3, COOR′, CN, and CONR′2. 1~12 -Alkyl, C 1~12 -Haloalkyl, cyclic C 3~8 -alkyl, C optionally substituted with one or more R' 5~18 - represents aryl; R''' is hydrogen, R'', CN, OR', (C=O)-R', COOR', CONR'2, straight or branched chain C 1~12 -Alkyl, C 2~12 -Alkenyl, C 2~12 -Alkynyl;Cyclic 3~8 -Alkyl, C 4~8 -Alkenyl, C 5~8 -Alkynyl; C 5~18 -aryl, C 7~19 -Aralkyl, C 7~19 -alkaryl; in the cyclic ring system, one or more carbon atoms are selected from the group consisting of N, O, and S(O) nany of the above groups 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 R' and R''' together with the atom to which they are attached or N, O, and S(O) n may form a 3-6 membered ring together with additional atoms selected from the group consisting of, which ring may be partially substituted by one or more of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; m and n represent integers, where n=0, 1 or 2; m=1 or 2.

[0018] According to another embodiment, the compound of general formula (Ia) further comprises

[0019] [ka] In one embodiment, the compound may be represented as: R x and R y are independently hydrogen, hydroxy, CN, NO2, COOR', S(O) n R'', OR', (C=O)-R'', C1~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; in the cyclic ring system, one or more carbon atoms are selected from the group consisting of N, O, and S(O) n or R x and R ytogether with the atom to which they are attached or together with a further atom selected from the group consisting of C, N, O, S, as well as C(=O), C(=S), S(O) m and SiR'2 to form a 3-7 membered ring, which may be optionally substituted in part by one or more of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; R x and R y all of the groups 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; All other substitutions A and R 4 ~R 10 is as defined in one of the above embodiments.

[0020] In one alternative preferred embodiment, R of the compound of formula (I) 1 is hydrogen, C 1~6 -Alkyl, C 1~6 -Alkoxy, C 1~6 -Alkylthio, C 1~6 -Haloalkyl, C 3~8 -cycloalkyl.

[0021] In one further embodiment, R of the compound of general formula (I) is 1 is hydrogen, C 1~6 -alkyl.

[0022] In one alternative preferred embodiment, R of the compound of formula (I) 2 and R 3 is 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.

[0023] In one alternative embodiment, R 1 and R 2 , R 2 and R 3 or R 1 and R 3 together with the atom to which they are attached or together with a further atom selected from the group consisting of C, N, O, S, as well as C(=O), C(=S), S(O) m and SiR'2 to form a 4-7 membered ring, which may be partially substituted by one or more of X, R', OR', SR', and CN.

[0024] In one alternative embodiment, the substituents R together with the atoms to which they are attached 1 and R 2 , R 2 and R 3 or R 1 and R 3 Preferred ring forming structures having the formula: are azetidine, pyrrolidine, imidazolidine, oxazolidine, piperidine, morpholine, thiomorpholine, piperazine, 1-methylpiperazine, 1-methylpyrrolidine, 1-methylpiperidine, 3-methyl-1,3-thiazinane.

[0025] In one alternative preferred embodiment, R of the compound of formula (I) 4 and R 5 is 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.

[0026] In one alternative preferred embodiment, R of the compound of formula (I) 6 and R 7 is 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.

[0027] R 4 and R 7 or R 5 and R 6 together with the atom to which they are attached or together with a further atom selected from the group consisting of C, N, O, S, as well as C(=O), C(=S), S(O) m and SiR'2 to form a 4-7 membered ring, which may be partially substituted by one or more of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2; R 4 , R 5 , R 6 and R 7 Each of 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.

[0028] In one alternative preferred embodiment, R on the compound of general formula (I) 8 and R 9 is hydrogen, 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 -Haloalkylthio, C 3~8 -Cycloalkyl, C 3~8 -Cycloalkoxy, C 3~8 -cycloalkylthio.

[0029] In one alternative embodiment, R 8 and R 9 may form a 3- to 6-membered ring together with the atom to which they are attached, or together with an additional atom selected from the group consisting of C, N, O, and S, which ring may be partially substituted by one or more of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2.

[0030] In one alternative preferred embodiment, R on the compound of general formula (I) 10 are hydrogen, X, CN, SCN, SF5, R'', OR'', NO2, NR''2, SiR'3, (C=O)-R'', S(O) n R'', C 1~8 -Alkyl-S(O) n R'', 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 -Cycloalkyloxy, C 3~8 -cycloalkylthio.

[0031] In one alternative embodiment, two R 10 together with the atom to which they are attached or together with a further atom selected from the group consisting of C, N, O, S, as well as C(=O), C(=S), S(O) mand SiR'2 to form a 4-10 membered ring, which may be optionally substituted in part by one or more of X, R', OR', SR', NR'2, SiR'3, COOR', CN, and CONR'2.

[0032] In another embodiment, preferred A is one or more R 10 phenyl, naphthalenyl, furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, imidazolyl, oxadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, benzimidazolyl, indazolyl; benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinazolinyl, cinnonyl.

[0033] In another embodiment, more preferred A is one or more R 10 and phenyl, naphthalenyl, thienyl, isothiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl substituted with .

[0034] In one alternative embodiment, R 1 ~R 10 may be further 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.

[0035] In one alternative embodiment, preferred compounds of general 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-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-(methylsulfinyl)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-(methylsulfinyl)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)methanimine; N-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-1-morpholinomethanimine; N-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-1-(piperidin-1-yl)methanimine; N-(2-chloro-4-(3-fluorobenzyl)-5-methylphenyl)-1-morpholinomethanimine; N-(2-chloro-4-(3-fluorobenzyl)-5-methylphenyl)-1-(piperidin-1-yl)methanimine; N-(2-chloro-4-(2-chlorobenzyl)-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-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-(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)methanimine; N-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-1-(piperidin-1-yl)methanimine; N-(4-(4-fluorobenzyl)-2,5-dimethylphenyl)-1-(piperidin-1-yl)methanimine; 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-chlorobenzyl)-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-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-(dimethylamino)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-(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-(trifluoromethoxy)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-dimethylphenyl)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-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'-(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 hydrochloride; 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; 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 It is. * Compound names were generated using Chemdraw Professional 16.0.

[0036] Any compound according to the invention may exist in one or more optical, geometric or chiral isomeric forms depending on the number of asymmetric centers in the compound.The invention therefore relates equally to all optical isomers and their racemic or scalemic mixtures (the term "scalemic" refers to a mixture of enantiomers in different proportions), as well as to mixtures of all possible stereoisomers in all proportions.Diastereoisomers and / or optical isomers can be separated according to methods known per se to those skilled in the art.

[0037] Also, any compound according to the present invention can exist in one or more geometric isomeric forms depending on the number of double bonds in the compound.Therefore, the present invention is equally related to all geometric isomers and all possible mixtures in all ratios.Geometric isomers can be separated according to the general methods known per se to those skilled in the art.

[0038] Also, any compound according to the present invention may exist in one or more amorphous or isomorphic or polymorphic forms depending on its preparation, purification, storage and various other influencing factors.The present invention therefore 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 according to general methods known per se to those skilled in the art.

[0039] In the above description, the term "alkyl", used alone or in compound words such as "alkylthio" or "haloalkyl", includes straight-chain or branched alkyl, for example methyl, ethyl, n-propyl, i-propyl, or the various butyl, pentyl or hexyl isomers.

[0040] "Alkenyl" includes straight-chain or branched alkenes, such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. "Alkenyl" also includes polyenes, such as 1,2-propadienyl and 2,4-hexadienyl.

[0041] "Alkynyl" includes straight-chain or branched alkynes, such as ethynyl, 1-propynyl, 2-propynyl, and the different butynyl, pentynyl and hexynyl isomers. "Alkynyl" can also include moieties that contain multiple triple bonds, such as 2,5-hexadiynyl.

[0042] "Cyclic alkyl" or "cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Cyclic alkenyl includes, for example, cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl. Cyclic alkynyl similarly refers to cyclic pentynyl, hexynyl, heptynyl, and octynyl.

[0043] The term "aryl" as used herein is a group that includes any carbon-based aromatic group, including, but not limited to, phenyl, naphthalene, biphenyl, anthracene, and the like. Aryl groups may be substituted or unsubstituted. Furthermore, aryl groups may be single ring structures or may include multiple ring structures that are fused ring structures or are linked through one or more bridging groups, such as carbon-carbon bonds.

[0044] The term "hetero" in reference to a ring refers to a ring in which at least one ring atom is not carbon and which may contain from 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur, provided that each ring contains no more than 4 nitrogens, no more than 2 oxygens, and no more than 2 sulfurs.

[0045] The term "heterocyclyl" means a cyclic ring system in which at least one ring atom is not carbon and can include a heteroatom independently selected from the group including nitrogen, oxygen, sulfur, phosphorus, boron, and the like.

[0046] The term "heterocyclyl" can be further classified as "non-aromatic heterocycle" and "aromatic heterocycle or heteroaryl."

[0047] The term "non-aromatic heterocycle" includes fused or non-fused 3- to 15-membered, preferably 3- to 12-membered saturated or fully or partially unsaturated heterocycles, monocyclic or polycyclic (spiro, fused, bridged, non-fused) heterocycles, in which the heteroatoms are selected from the group of oxygen, nitrogen and sulfur; if a ring contains more than one oxygen atom, they are not directly adjacent; non-limiting examples of non-aromatic heterocycles are oxetanyl, oxiranyl; aziridinyl; thiiraniyl; This definition also applies to heterocyclyl as part of a compound substituent, such as heterocyclylalkyl (a heterocyclic group containing an alkyl moiety as defined above), unless specifically defined elsewhere.

[0048] The term "heteroarylaryl" as used herein refers to a group containing a fused or non-fused 3- to 15-membered, preferably 3- to 12-membered, more preferably 5- or 6-membered monocyclic or polycyclic unsaturated ring system containing heteroatoms selected from the group of oxygen, nitrogen, sulfur, phosphorus, boron, and the like.

[0049] Non-limiting examples of 5-membered 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-oxazolyl. These include azol-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 the like.

[0050] Non-limiting examples of 6-membered 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 the like.

[0051] Non-limiting examples of benzo-fused 5-membered 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-2-yl. 1,3-benzothiazol-2-yl; 1,3-benzothiazol-4-yl; 1,3-benzothiazol-5-yl; 1,3-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; 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 the like.

[0052] Non-limiting examples of benzo-fused 6-membered 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 the like.

[0053] The term "aralkyl" refers to an aryl hydrocarbon group containing an alkyl portion as defined above. Examples include benzyl, phenylethyl, and 6-naphthylhexyl. As used herein, the term "aralkenyl" refers to an aryl hydrocarbon group containing an alkenyl portion as defined above and an aryl portion as defined above. Examples include styryl, 3-(benzyl)prop-2-enyl, and 6-naphthylhex-2-enyl.

[0054] The term "alkaryl" refers to an aryl group bearing an alkyl group; as used herein, the term "alkaryl" includes both substituted and unsubstituted groups. One example of an alkaryl group is the 4-methylphenyl group.

[0055] "Alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.

[0056] "Alkylthio" includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.

[0057] The term "halogen", either alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine.

[0058] The total number of carbon atoms in a substituent is indicated by the prefix "C i~j ", where i and j are numbers from 1 to 21. For example, C 1~3 Alkoxy refers to methoxy through propoxy. In the above list, when the compound of formula (I) contains one or more heterocyclic rings, all substituents are attached to these rings through an available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.

[0059] When a compound is substituted with a substituent having a subscript indicating the number of substituents that may be more than one, the substituents (if more than one) are independently selected from the group of defined substituents. Additionally, when a subscript indicates a range, e.g., (R i~j In the case of, the number of substituents may be selected from integers i to j, inclusive.

[0060] Groups include substituents which may be hydrogen, e.g. R 1 or R 2 When this substituent is taken as hydrogen, it is understood to be equivalent to the unsubstituted said group.

[0061] The present invention further relates to a composition for controlling undesirable microorganisms, comprising at least one compound of formula (I) and one or more inert carriers, which further comprise agriculturally suitable adjuvants, solvents, diluents, surfactants and / or extenders, etc.

[0062] The present invention further relates to compositions for controlling unwanted microorganisms comprising at least one compound of formula (I) and / or one or more active compatible compounds selected from fungicides, bactericides, acaricides, insecticides, molluscicides, herbicides, biopesticides, plant growth regulators, antibiotics, fertilizers and / or mixtures thereof.

[0063] The present invention further relates to a composition, wherein the concentration of the compound having general formula (I) ranges 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.

[0064] The present invention also relates to a method for controlling unwanted microorganisms, wherein a compound of formula (I) is applied to the microorganisms and / or their habitat.

[0065] The present invention further provides a method for protecting seeds against undesirable microorganisms by using seeds treated with at least one compound of formula (I).

[0066] The compounds of formula (I) may have strong antibacterial activity and may be used in agricultural or horticultural crop protection, and in the protection of such materials, to control unwanted microorganisms, such as fungi, insects, mites, nematodes and bacteria.

[0067] The compounds of formula (I) may have very good fungicidal properties and may be used in crop protection, for example for controlling Plasmodiophora, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Fungi imperfecti.

[0068] The compounds of formula (I) may be used in crop protection as molluscicides, for example for controlling nematodes, pseudomediums and Tryplonchida.

[0069] The compounds of formula (I) may be used as insecticides in crop protection, for example for the control of Lepidoptera, Coleoptera, Hemiptera, Homoptera, Thysanoptera, Diptera, Orthoptera and Isoptera.

[0070] The compounds of formula (I) may be used in crop protection as acaricides, for example for controlling Erioidea, Tetranychidae, Eupodoidea and Tarsorrhexidae.

[0071] The compounds of formula (I) may be used as fungicides in crop protection, for example for the control of Pseudomonadaceae, Rhizobiumaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

[0072] The compounds of formula (I) can be used as herbicides and can be effective against a wide range of economically important harmful monocotyledonous and dicotyledonous plants.Monocotyledonous broadleaf weed species can include Avena sativa, Ryegrass, Alpine foxtail, Reed canary, Barnyard millet, Digitaria ciliaris, Setaria and Cyperus species from annual plant group, and perennial species of Wheatgrass, Cyperus dactylon, Imperata cyperus and Sorghum, as well as perennial Cyperus species. Dicotyledonous broadleaf weed species may include annual species such as Cleome, Viola, Speedwell, Lamium, Chickweed, Amaranth, White Mustard, Sweet Potato, Fern, Deutzia, and Abutilon, and perennial species such as Convolvulus, Thistle, Rumex, and Artemisia. Harmful plants on rice, such as Echinochloa, Salvia, Scutellaria, Scutellaria, Bulbul, and Cyperus, may be controlled by the compounds of formula (I).

[0073] The compounds of formula (I) can be used for curative or protective control of phytopathogenic fungi.Therefore, the present invention also relates to a curative and protective method for controlling phytopathogenic fungi by using the active ingredient or composition of the present invention, which is applied to seeds, plants or plant parts, fruits, or the soil in which plants grow.

[0074] The compounds of formula (I) may be used to control or prevent plant pathogens, bacteria, insects, nematodes, mites in agricultural and / or horticultural crops.

[0075] The compounds of formula (I) may be used in crop protection, agricultural crops being cereals, maize, rice, soybean and other legumes, fruit and fruit trees, nuts and nut trees, citrus and citrus trees, any horticultural plant, cucurbit, oil plants, tobacco, coffee, tea, cocoa, sugar beet, sugar cane, cotton, potato, tomato, onion, pepper and other plants, and ornamental plants.

[0076] According to the present invention, as defined above, carrier is a natural or synthetic organic or inorganic material with which active ingredient is mixed or combined for better application, especially for application to plant or plant part or seed.Carrier, which may be solid or liquid, should generally be inert and suitable for use in agriculture.

[0077] Useful solid carriers include, for example, ammonium salts and natural rock flours, such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, as well as synthetic rock flours, such as micronized silica, alumina and silicates; useful solid carriers for granules include, for example, crushed and fragmented natural rocks, such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic powders, as well as granules of organic materials, such as paper, sawdust, coconut shells, corn cobs and tobacco stalks; useful emulsifiers and / or foaming agents include, for example, nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, such as alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, as well as protein hydrolysates; suitable dispersants include nonionic and / or ionic substances, such as alcohol-POE and / or -POP ethers, acids and / or POP. These are from the classes of POE esters, alkylaryl and / or POP POE ethers, fatty 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 aryl sulfonates and alkyl or aryl phosphates, or the corresponding PO-ether adducts. Furthermore, oligomers or polymers, such as those obtained from vinyl monomers, acrylic acid, EO and / or PO alone or in combination, for example, with (poly)alcohols or (poly)amines, are suitable. It is also possible to use lignin and its sulfonic acid derivatives, unmodified and modified cellulose, aromatic and / or aliphatic sulfonic acids, as well as their adducts with formaldehyde.

[0078] The active ingredient may be applied as it is, or may be converted into a special formulation, or may be prepared from it in its formulation or use form, such as ready-to-use solutions, emulsions, aqueous or oily suspensions, powders, wettable powders, pastes, soluble powders, soluble tablets, dusts, soluble granules, granules for spreading, suspoemulsion concentrates, natural products impregnated with the active ingredient, synthetic materials impregnated with the active ingredient, fertilizers, and even in microencapsulated form in polymeric materials. Application is achieved in the usual manner, for example by watering, spraying, misting, seedbed boxes, scattering, dusting, foaming, spreading, etc. It is also possible to distribute the active ingredient by ultra-low-volume methods, or to inject the active ingredient preparation or the active ingredient itself into the soil. It is also possible to treat the seeds of plants.

[0079] The active ingredients may be further converted into nanoformulations with the aim of further improving water solubility, thermal stability, bioavailability, organoleptic properties, and physiological performance.

[0080] Additionally, the choice of formulation type will depend on the particular application.

[0081] The formulations mentioned can be prepared in a manner known per se, for example by mixing the active ingredient with at least one customary extender, solvent or diluent, emulsifier, dispersant and / or binder or fixative, wetting agent, water repellent, where appropriate drying agents and UV stabilizers, and also where appropriate dyes and pigments, defoamers, preservatives, auxiliary thickeners, adhesives, gibberellins and also other processing auxiliaries.

[0082] The invention includes not only formulations which are already ready to use and can be distributed onto plants or seeds by suitable equipment, but also commercial concentrates which must be diluted with water before use.

[0083] The adjuvants used may be substances suitable for imparting certain properties, such as certain technical properties and / or certain biological properties, to the composition itself and / or to the preparations obtained therefrom (e.g. spray liquids, seed dressings). Typical adjuvants include extenders, solvents and carriers.

[0084] Suitable extenders are, for example, water, polar and non-polar organic chemical liquids, such as aromatic and non-aromatic hydrocarbons (e.g. paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (optionally substituted, etherified and / or esterified), ketones (e.g. acetone, cyclohexanone), esters (including fats and oils), and (poly)ethers, unsubstituted and substituted amines, amides, lactams (e.g. N-alkylpyrrolidones) and lactones, sulfones, and sulfoxides (e.g. dimethyl sulfoxide).

[0085] Liquefied gaseous extenders or carriers are understood to mean liquids which are gaseous at standard temperature and pressure, such as aerosol propellants, such as halohydrocarbons, or, among others, butane, propane, nitrogen and carbon dioxide.

[0086] In the formulations it is possible to use tackifiers such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids, such as cephalin and lecithin, and also synthetic phospholipids. Further additives may be mineral, vegetable and methylated seed oils.

[0087] When the extender used is water, it is also possible to use organic solvents, for example as auxiliary solvents.Useful liquid solvents are essentially aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, such as petroleum fractions, alcohols, such as butanol or glycols and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethylsulfoxide, or else water.

[0088] The composition comprising the compound of formula (I) may further comprise further components, such as surfactants.Suitable surfactants are emulsifiers and / or foaming agents, dispersants or wetting agents with ionic or nonionic properties, or mixtures of these surfactants.Examples thereof are salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic 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 acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty esters of polyols, and derivatives of compounds containing sulfates, sulfonates and phosphates, such as alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates, protein hydrolysates, lignosulfite effluents, and methylcellulose. The presence of a surfactant is necessary when one of the active ingredients and / or one of the inert carriers is insoluble in water and when application is carried out with water. The proportion of surfactant is 5 to 40 percent by weight of the composition of the invention.

[0089] It is possible to use inorganic pigments, such as dyes such as iron oxide, titanium oxide and Prussian blue, as well as organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

[0090] Further additives may be flavourings, mineral or vegetable, optionally modified oils, waxes and nutrients (including micronutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

[0091] The additional component may be a stabilizer, such as a low temperature stabilizer, a preservative, an antioxidant, a light stabilizer, or other agent that improves chemical and / or physical stability.

[0092] Where appropriate, other additional ingredients may be present, such as protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrating agents, stabilizers, sequestering agents, complex formers, etc. In general, the active ingredient may be combined with any solid or liquid additive commonly used for formulation purposes.

[0093] The formulations generally contain from 0.05 to 99%, from 0.01 to 98%, preferably from 0.1 to 95%, more preferably from 0.5 to 90%, most preferably from 10 to 70% by weight of active ingredient.

[0094] The above-mentioned formulations may be used to control undesirable microorganisms, whereby a composition comprising a compound of formula (I) is applied to the microorganisms and / or their habitat.

[0095] The compounds of formula (I) according to the present invention and salts, N-oxides, metal complexes, stereoisomers or polymorphs can be used as such or in their formulations, and can be mixed with known mixing partners, for example to broaden the spectrum of activity or to prevent the development of resistance. Useful mixing partners include, for example, known fungicides, insecticides, acaricides, molluscicides, biopesticides and bactericides. Mixtures with other known active ingredients, such as herbicides, or with fertilizers and growth regulators, safeners and / or semiochemicals are also possible.

[0096] Examples of such chemical components are given herein without limitation. Some of them are specified herein by their common names, which are known and described, for example, in The Pesticide Manual 17th Ed., or can be found on the Internet (for example, at www.alanwood.net / pesticides). Others are described by their systematic names according to the IUPAC nomenclature.

[0097] All named mixture partners of classes (A) to (O) described below can optionally form salts with suitable bases or acids, if their functional groups allow, and can appear as stereoisomers, even if not specifically mentioned in each case, or as polymorphs, which are understood to be included in this specification. Examples of these are as follows:

[0098] A) Inhibitors of ergosterol biosynthesis, such as (A01) aldimorph, (A02) azaconazole, (A03) bitertanol, (A04) bromuconazole, (A05) cyproconazole, (A06) diclobutrazol, (A07) difenoconazole, (A08) diniconazole, (A09) diniconazole-M, (A10) dodemorph, (A11) dodemorph acetate, (A12) epoxiconazole, (A13) etaconazole, (A14) fenarimol, (A15) fenbuconazo (A16) fenhexamid, (A17) fenpropidin, (A18) fenpropimorph, (A19) fluquinconazole, (A20) flurprimidol, (A21) flusilazole, (A22) flutriafol, (A23) fluconazole, (A24) fluconazole-cis, (A25) hexaconazole, (A26) imazalil, (A27) imazalil sulfate, (A28) imibenconazole, (A29) ipconazole, (A30) metconazole, (A31) microbenconazole, (A32) hexaconazole, (A33) hexaconazole, (A34) hexaconazole, (A35) hexaconazole, (A36) hexaconazole, (A37) hexaconazole, (A38) hexaconazole, (A39) hexaconazole, (A40) hexaconazole, (A41) hexaconazole, (A42) hexaconazole, (A43) hexaconazole, (A44) hexaconazole, (A45) hexaconazole, (A46) hexaconazole, (A47) hexaconazole, (A48) hexaconazole, (A49) hexaconazole, (A50) hexaconazole, (A51) hexaconazole, (A52) hexaconazole, (A53) hexaconazole, (A54) hexaconazole, (A55) hexaconazole, (A56) hexaconazole, (A57) hexaconazole, (A58) hexaconazole, (A59) hexaconazole, (A60) hexaconazole, (A61) hexaconazole, (A62) hexaconazole Tanil, (A32) Naftifine, (A33) Nuarimol, (A34) Oxpoconazole, (A35) Paclobutrazol, (A36) Pefurazoate, (A37) Penconazole, (A38) Piperalin, (A39) Prochloraz, (A40) Propiconazole, (A41) Prothioconazole, (A42) Pyributicarb, (A43) Pyrifenox, (A44) Quinconazole, (A45) Simeconazole, (A46) Spiroxamine, (A47) Tebuconazole, (A48) Terbinaf , (A49) tetraconazole, (A50) triadimefon, (A51) triadimenol, (A52) tridemorph, (A53) triflumizole, (A54) triforine, (A55) triticonazole, (A56) uniconazole, (A57) uniconazole-p, (A58) biniconazole, (A59) voriconazole, (A60) 1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, (A61) methyl 1-(2,2-dimethyl-2,3-Dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate, (A62) N'-{5-(difluoromethyl)-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-imidazo (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-(arylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate (A69) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-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-triazole-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-(arylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (A75) 5-(arylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (A76) 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole (A77) 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-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, ,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-triazole-3-thione, (A80) 2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-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-hydroxy-2,6,6-trimethylheptan-4-yl]-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-triazole-3-thione, (A83) 2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-Triazole-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 1-(1H-1,2,4-triazol-1-yl)propan-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-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol; (A90) (2R)-2-(1- (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-dichlorocyclopropyl]-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.

[0099] B) Inhibitors of the respiratory chain at complex I or II, such as (B01) bixafen, (B02) boscalid, (B03) carboxin, (B04) cypropamide, (B05) diflumetrim, (B06) fenfuram, (B07) fluopyram, (B08) flutolanil, (B09) fluxapyroxad, (B10) furametpyr, (B11) flumecyclox, (B12) isopyrazam (mixture of syn-epimer racemates 1RS,4SR,9RS and anti-epimer racemates 1RS,4SR,9SR), (B13) isopyrazam (anti-epimer racemates 1RS,4SR,9SR), (B14) isopyrazam (mixture of syn-epimer racemates 1RS,4SR,9SR), (B15) isopyrazam (mixture of syn-epimer racemates 1RS,4SR,9SR), (B16) isopyrazam (mixture of syn-epimer racemates 1RS,4SR,9SR), (B17) isopyrazam (mixture of syn-epimer racemates 1RS,4SR,9SR), (B18) isopyrazam (mixture of syn-epimer racemates 1RS,4SR,9SR), (B19) isopyrazam (mixture of syn-epimer racemates 1RS,4SR,9SR), (B20) isopyrazam (mixture of syn-epimer racemates 1RS,4SR,9SR), (B21) isopyrazam (mixture of syn-epimer racemates 1RS,4SR,9SR), (B22) isopyrazam (mixture of syn-epimer racemates 1RS,4SR,9SR), (B23) isopyrazam (mixture of syn-epimer racemates 1RS (B14) Isopyrazam (anti-epimer enantiomer 1R,4S,9S), (B15) Isopyrazam (anti-epimer enantiomer 1S,4R,9R), (B16) Isopyrazam (syn-epimer racemate 1RS,4SR,9RS), (B17) Isopyrazam (syn-epimer enantiomer 1R,4S,9R), (B18) Isopyrazam (syn-epimer enantiomer 1S,4R,9S), (B19) Mepronil, (B20) Oxycarboxin, (B21) Penflufen, (B22) Penthiopyrad , (B23) pydiflumetofen, (B24) sedaxane, (B25) thifluzamide, (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)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl (B29) N-[1-(2,4-dichlorophenyl)-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-Methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (B33) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-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-pyrazole-4-carboxamide amide, (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-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (B37) 1-methyl-3-(trifluoromethyl)-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole (B38) 1-methyl-3-(trifluoromethyl)-N-[(3S)-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) 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-di (B41) 1,3,5-trimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (B42) 1,3,5-trimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (B43) 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-pyrazole-4-carboxamide, (B47) N-(4'-chlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (B48) N-(2',4'-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H -pyrazole-4-carboxamide, (B49) 3-(difluoromethyl)-1-methyl-N-[4'-(trifluoromethyl)biphenyl-2-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-pyrazole-4-carboxamide, ( B52) 5-fluoro-1,3-dimethyl-N-[4'-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (B53) 2-chloro-N-[4'-(prop-1-yn-1-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-yn-1-yl)biphenyl-2-yl] (B57) N-(4'-ethynylbiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-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, (B63) 4-(difluoromethyl)-2-methyl-N-[4'-(trifluoromethyl)biphenyl-2-yl]-1,3-thiazole-5-carboxamide, (B64) 5-fluoro-N-[4'-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide, (B65) 2-chloro-N-[4'-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl] (B63) 3-(difluoromethyl)-N-[4'-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide, (B64) 5-fluoro-N-[4'-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide, (B65) 2-chloro-N-[4'-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]- -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-pi 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.

[0100] C) Inhibitors of the respiratory chain at complex III, such as (C01) amethoctrazine, (C02) amisulbrom, (C03) azoxystrobin, (C04) cyazofamid, (C05) cumoxystrobin, (C06) cumoxystrobin, (C07) dimoxystrobin, (C08) enoxastrobin, (C09) famoxadone, (C10) fenamidone, (C11) phenaminestrobin, (C12) flufenoxystrobin, (C13) fluoxastrobin, (C14) kresoxim-methyl, (C15) metominostrobin , (C16) mandestrobin, (C17) orysastrobin, (C18) picoxystrobin, (C19) pyraclostrobin, (C20) pyrametostrobin, (C21) pyraoxystrobin, (C22) pyribencarb, (C23) triclopyricarb, (C24) trifloxystrobin, (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}acetamide, (C28)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}- 2-(Methoxyimino)-N-methylacetamide, (C29) Fenaminostrobin, (C30) 5-Methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)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-trimethylcyclohexyl)-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-(methoxyimino)-N,3-dimethylpent-3-enamide.

[0101] D) Inhibitors of mitosis and cell division, such as (D01) benomyl, (D02) carbendazim, (D03) chlorphenazole, (D04) diethofencarb, (D05) ethaboxam, (D06) fluopicolide, (D07) albendazole, (D08) pencycuron, (D09) thiobendazole, (D10) thiophanate-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-trifluorophenyl)pyridazine.

[0102] E) Compounds capable of having a multisite of action, for example (E01) Bordeaux mixture, (E02) captafol, (E03) captan, (E04) chlorothalonil, (E05) copper hydroxide, (E06) copper naphthenate, (E07) copper oxide, (E08) copper oxychloride, (E09) copper(2+) sulfate, (E10) dichlofluanid, (E11) dithianone, (E12) dodine, (E13) dodine free base, (E14) ferbam, (E15) fluorofolpet, (E16) folpet, (E17) guazatine, (E18) guazatine, (E20) iminoctadine albesilate, (E21) iminoctadine triacetate, (E22) mancopper, (E23) mancozeb, (E24) maneb, (E25) metiram, (E26) metiram zinc, (E27) oxine-copper, (E28) propamidine, (E29) propineb, (E30) sulphur preparations containing sulphur and calcium polysulphide, (E31) thiram, (E32) tolylfluanid, (E33) zenib, (E34) ziram, (E35) anilazine.

[0103] F) Compounds capable of inducing host defense, such as (F01) acibenzolar-S-methyl, (F02) isotianil, (F03) probenazole, (F04) tiadinil, (F05) laminarin.

[0104] G) Inhibitors of amino acid and / or protein biosynthesis, such as (G01) andoprim, (G02) blasticidin-S, (G03) cyprodinil, (G04) kasugamycin, (G05) kasugamycin hydrochloride hydrate, (G06) mepanipyrim, (G07) ​​pyrimethanil, (G08) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (G09) oxytetracycline, (G10) streptomycin.

[0105] H) Inhibitors of ATP production, such as (H01) fentin acetate, (H02) fentin chloride, (H03) fentin hydroxide, (H04) silthiofam.

[0106] I) Inhibitors of cell wall synthesis, such as (I01) benthiavalicarb, (I02) dimethomorph, (I03) flumorph, (I04) iprovalicarb, (I05) mandipropamid, (I06) polyoxins, (I07) polyoxorim, (I08) validamycin A, (I09) valifenalate, (I10) polyoxin B, (I11) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (I12) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

[0107] J) Inhibitors of lipid and membrane synthesis, such as (J01) biphenyl, (J02) chloroneb, (J03) dicloran, (J04) edifenphos, (J05) etridiazole, (J06) iodocarb, (J07) iprobenfos, (J08) isoprothiolane, (J09) propamocarb, (J10) propamocarb hydrochloride, (J11) prothiocarb, (J12) pyrazophos, (J13) quintozene, (J14) tecnazene, (J15) toclofos-methyl.

[0108] K) Inhibitors of melanin biosynthesis, such as (K01) carpropamid, (K02) diclocymet, (K03) fenoxanil, (K04) phthalide, (K05) pyroquilon, (K06) tolprocarb, (K07) tricyclazole.

[0109] L) Inhibitors of nucleic acid synthesis, such as (L01) benalaxyl, (L02) benalaxyl-M (chiralaxyl), (L03) bupirimate, (L04) clozylacon, (L05) dimethirimol, (L06) ethirimol, (L07) furalaxyl, (L08) hymexazole, (L09) metalaxyl, (L10) metalaxyl-M (mefenoxam), (L11) ofrace, (L12) oxadixyl, (L13) oxolinic acid, (L14) octhilinone.

[0110] M) Signal transduction inhibitors, such as (M01) clozolinate, (M02) fenpiclonil, (M03) fludioxonil, (M04) iprodione, (M05) procymidone, (M06) quinoxyfen, (M07) vinclozolin, (M08) proquinazide.

[0111] N) Compounds which may act as uncouplers, such as (N01) binapacryl, (N02) dinocap, (N03) ferimzone, (N04) fluazinam, (N05) meptyldinocap.

[0112] O) Further compounds, such as (O01) benthazole, (O02) bethoxadin, (O03) capsimycin, (O04) carvone, (O05) quinomethionate, (O06) pyriophenone (clazafenone), (O07) kufuraneb, (O08) cyflufenamid, (O09) cymoxanil, (O10) cyprosulfamide, (O11) dazomet, (O12) debacarb, (O13) dichlorophen, (O14) diclobentiazox, (O15) diclomedine, (O16) difenzoquat, (O17) difenzoquat methylsulfate ate, (O18) diphenylamine, (O19) ecomate, (O20) fenpyrazamine, (O21) fenhexamine, (O22) flumetober, (O23) fluoroimide, (O24) flusulfamide, (O25) fluthianil, (O26) fosetyl-aluminum, (O27) fosetyl-calcium, (O28) fosetyl-sodium, (O29) hexachlorobenzene, (O30) irumamycin, (O31) isotianil, (O32) methasulfocarb, (O33) methylisothiocyanate, (O34) metrafenone, ( O35) Mildomycin, (O36) Natamycin, (O37) Nickel dimethyldithiocarbamate, (O38) Nitrotar-isopropyl, (O39) Oxamocarb, (O40) Oxyfenthiin, (O41) Pentachlorophenol and salts, (O42) Fenothrin, (O43) Picarburazox, (O44) Phosphoric acid and salts, (O45) Propamocarb-focetylate, (O46) Propanosine-sodium, (O47) Pyrimorph, (O48) Pyraziflumid, (O49) Pyrrolnitrin, (O50) Tebufloquine, ( O51) Tecloftalam, (O52) Tornifanide, (O53) Triazoxide, (O54) Trichlamide, (O55) Zaliramide, (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-methylpropionate, (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-[(5S)-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-methoxyphenoxy)-3,3-dimethylbutane -2-yl-1H-imidazole-1-carboxylate, (O61) 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine, (O62) 2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one, (O63) 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone, (O64) 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro 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, (O69) 2-phenylphenol and salts, (O70) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (O71) 3,4,5-trichloropyridine-2,6-Dicarbonitrile, (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-sulfonohydra 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (O77) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (O78) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (O79) 5-methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine, (O80) ethyl(2Z)-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, (O85) N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotine amide, (O86) N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotinamide, (O87) N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide, (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-thiazole-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-thiazole-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-thiazole-4-carboxamide, (O93) pentyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbame ester, (O94) phenazine-1-carboxylic acid, (O95) quinolin-8-ol, (O96) quinolin-8-ol sulfate (2:1), (O97) tert-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (O98) (5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone, (O99) N-[2-(4-{[3-(4-chlorophenyl)prop-2-yne-1-yl]amino]oxy]methyl]pyridin-2-yl}carbamate, -yl]oxy}-3-methoxyphenyl)ethyl]-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) (S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (O1 06) (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (O107) 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 (O113) N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (O114) N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (O115) N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (O116) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (O117) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide amide, (O118) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-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- Cyclopropyl-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-cyclopropy-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-pyrazole-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-methylimidoformamide,(O139) N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide, (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, (O14 6) 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (O147) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (O148) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (O149) 4-(2-bromo-4-fluorophenyl)- N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (O150) 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (O151) 4-(2-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-pyrazol-5-amine,(O153) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-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-pyrazol-5-amine, (O156) N'-(4-{3-[(difluoromethyl)sulfanyl] phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (O157) N'-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (O158) N'-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (O159) N'-(2,5-dimethyl-4-{3- [(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (O160) N'-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (O161) N'-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (O162) N'-(2,5-dimethyl- 4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (O163) N'-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (O164) N'-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (O165) N'-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidamide, (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-yn-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-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (O1 69) 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, (O1 71) 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-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (O174) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-fluoro-6 -(prop-2-yn-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-yl]ethanone, (O176) 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-yl]ethanone, 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 yl}phenyl methanesulfonate, (O178) 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}phenyl methanesulfonate2-Oxazol-5-yl}-3-chlorophenyl methanesulfonate, (O180) 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-methoxypicolinamido}-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl isobutyrate.

[0113] As mentioned above, the compounds of formula (I) may be mixed with one or more compatible active compounds selected from the classes of insecticides / acaricides / nematicides, which are designated herein by their common names, which are known and described, for example, in The Pesticide Manual, 17th Edition, or which can be found on the Internet (e.g., www.alanwood.net / pesticides).

[0114] (1) Acetylcholinesterase (AChE) inhibitors, such as carbamates, such as alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb, or organophosphates, such as acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP ... Lotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famfur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyaphos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, ometho. phthalate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimphos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothion.

[0115] (2) GABA-gated chloride channel antagonists, for example, cyclodiene organochlorins, such as chlordane and endosulfan or phenylpyrazoles (fiproles), such as ethiprole and fipronil.

[0116] (3) Sodium channel modulators / voltage-dependent sodium channel blockers, for example, pyrethroids, for example, acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans- isomer)], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, fenothrin [(1R)-trans-isomer)], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer)], tralomethrin and transfluthrin or DDT or methoxychlor.

[0117] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, for example, neonicotinoids, such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.

[0118] (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators, such as the spinosyns, e.g., spinetoram and spinosad.

[0119] (6) GluCl-gated chloride channel allosteric modulators, such as the avermectins / milbemycins, e.g., abamectin, emamectin benzoate, lepimectin and milbemectin.

[0120] (7) Juvenile hormone-like substances, such as juvenile hormone analogues, for example, hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

[0121] (8) Active compounds with unknown or non-specific mechanisms of action, such as alkyl halides (e.g., methyl bromide and other alkyl halides), or chloropicrin or fluorides or borates or tartar emetics or methyl isocyanate generators.

[0122] (9) Chordal organ TRPV channel modulators, such as pyridine azomethine derivatives, such as pymetrozine and pyrifluquinazone or flonicamide.

[0123] (10) Mite growth inhibitors, such as clofentezine, hexythiazox and diflovidazine or etoxazole.

[0124] (11) Microbial disruptors of insect midguts, such as Bacillus thuringiensis subspecies israelensis, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and Bacillus sphaericus, as well as BT crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, and Cry1A. 105, Cry2Ab, Vip3a, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1.

[0125] (12) Inhibitors of mitochondrial ATP synthase, for example organotin acaricides such as azocyclotin, cyhexatin and fenbutatin oxide or diafenthiuron or propargite or tetradifon.

[0126] (13) Uncouplers of oxidative phosphorylation that act via disruption of the proton gradient, such as chlorfenapyr, DNOC, and sulfluramide.

[0127] (14) Nicotinic acetylcholine receptor (nAChR) channel blockers, such as bensultap, cartap hydrochloride, thiocyclam and thiosultap-sodium.

[0128] (15) Inhibitors of chitin biosynthesis (type 0), such as bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxyuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, and triflumuron.

[0129] (16) Inhibitors of chitin biosynthesis (type 1), such as buprofezin.

[0130] (17) Molting disruptors (especially in Dipterans), such as cyromazine.

[0131] (18) Ecdysone receptor agonists, such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0132] (19) Octopamine receptor agonists, such as amitraz.

[0133] (20) Mitochondrial complex III electron transport inhibitors, such as hydramethylnon or acequinocyl or fluacrypyrim or bifenazate.

[0134] (21) Mitochondrial complex I electron transport inhibitors, for example METI acaricides and insecticides, such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Derris).

[0135] (22) Voltage-dependent sodium channel blockers, such as indoxacarb or metaflumizone.

[0136] (23) Inhibitors of acetyl-CoA carboxylase, such as tetronic acid and tetramic acid derivatives, such as spirodiclofen, spiromesifen and spirotetramat.

[0137] (24) Mitochondrial complex IV electron transport inhibitors, such as phosphides, for example aluminum phosphide, calcium phosphide, zinc phosphide and phosphines or cyanides.

[0138] (25) Mitochondrial complex II electron transport inhibitors, such as beta-ketonitrile derivatives, such as cyenopyrafen and cyflumetofen or carboxanilides.

[0139] (28) Ryanodine receptor modulators, for example diamides, such as chlorantraniliprole, cyantraniliprole and flubendiamide.

[0140] (29) Chordotonal organ modulators with undefined target sites, e.g., flonicamide.

[0141] Further active ingredients with unknown or undetermined modes of action, for example afidopiropen, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, quinomethionate, cryolite, cyclaniliprole, cycloxapride, cyhalodiamide, dichloromezothiaz, dicofol, diflobidazine, flometoquin, fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin, flufiprole , fluhexafon, fluopyram, fluralaner, fluxamethamide, fufenozide, guadipyr, heptafluthrin, imidaclothiz, iprodione, lotilaner, meperfluthrin, paichongding, piflubumid, pyridalyl, pyrifluquinazone, pyriminostrobin, sarolaner, tetramethylfluthrin, tetranipiprole, tetrachlorantraniliprole, thioxazaphene, triflumezopyrim and iodomethane; and Bacillus firmus (Bacillus firmus) (I-1582, BioNeem, Votivo), and the following known active compounds: 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (known from WO2006043635), {1'-4[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4'-piperidine]-1(2H)-yl}(2-chloropyridine- 4-yl)methanone (known from WO2003106457), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO2006003494), 3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO2009049851), 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1,8-Diazaspiro[4.5]dec-3-en-4-ylethyl 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)pyrimidine (known from WO2003076415), PF1364 (CAS registration number 1204776-60-2), methyl-2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)- 1H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2-methylhydrazine carboxylate (known from WO2005085216), methyl-2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-ethylhydrazine carboxylate (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-methylhydrazine carboxylate (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-ethylhydrazine carboxylate (known from WO2005085216), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloropyridine- 2-yl)-1H-pyrazole-5-carboxamide (known from CN102057925), 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxidothietan-3-yl)benzamide (known from WO2009080250), N-[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (known from WO2012029672), 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-oleate (known from WO2009099929), 1-[(6-chloropyridin-3-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-oleate (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-butylcarbamoyl)-4-chloro-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (known from WO2008134969), butyl-[2-(2,4-dichlorophenyl)-3-oxo-4-oxaspiro[4.5]dec-1-en-1-yl]carbonate (disclosed 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).

[0142] The compounds of formula (I) may be used to treat a number of fungal pathogens. Non-limiting examples of fungal disease pathogens that can be treated according to the present invention include: Diseases caused by the following powdery mildew pathogens, for example Blumeria species, for example Blumeria graminis; Podosphaera species, for example Podosphaera leucotricha; Sphaerotheca species, for example Sphaerotheca fuliginea; Uncinula species, for example Uncinula necator; Erysiphe species, for example Erysiphe cichoraceau; Diseases caused by the following rust pathogens, for example Gymnosporangium species, for example Gymnosporangium sabinae; Hemileia species, for example Hemileia vastatrix; Phakopsora species, for example Phakopsora pachyrhizi or Phakopsora meibomiae; Puccinia species, for example Puccinia recondita, Puccinia graminis or Puccinia striiformis; Uromyces species, for example Uromyces appendiculatus; Diseases caused by pathogens from the following groups of oomycetes, for example Albugo species, such as Albugo candida; Bremia species, such as Bremia lactucae; Peronospora species, such as Peronospora pisi or P. brassicae; Phytophthora species, such as Phytophthora infestans; Plasmopara species, such as Plasmopara viticola; Pseudoperonospora species, such as Pseudoperonospora humuli or Pseudoperonospora cubensis. cubensis);Pythium species, e.g., Pythium ultimum; Leaf blight and wilt diseases caused by, for example, Alternaria species, such as Alternaria solani; Cercospora species, such as Cercospora beticola; Cladiosporum species, such as Cladiosporium cucumerinum; Cochliobolus species, such as Cochliobolus sativus (conidiomorph: Drexlera, synonym: Helminthosporium); or Cochliobolus miyabeanus; Colletotrichum species, such as Colletotrichum lindemuthanium; Cycloconium species, such as Cycloconium oleaginum; oleaginum; Diaporthe species, for example, Diaporthe citri; Elsinoe species, for example, Elsinoe fawcettii; Gloeosporium species, for example, Gloeosporium laeticolor; Glomerella species, for example, Glomerella cingulata; Guignardia species, for example, Guignardia bidwelli; Leptosphaeria species, for example, Leptosphaeria maculans; Magnaporthe species, for example, Magnaporthe grisea; Microdochium species, for example, Microdochium nivale nivale); Mycosphaerella species, for example Mycosphaerella graminicola, Mycosphaerella arachidicola or Mycosphaerella fijiensis;Phaeosphaeria species, for example Phaeosphaeria nodorum; Pyrenophora species, for example Pyrenophora teres or Pyrenophora tritici repentis; Ramularia species, for example Ramularia collo-cygni or Ramularia areola; Rhynchosporium species, for example Rhynchosporium secalis; Septoria species, for example Septoria apii or Septoria lycopersici; Stagonospora species, for example Stagonospora nodorum. nodorum); Typhula species, e.g., Typhula incarnata; Venturia species, e.g., Venturia inaequalis; Root and stem diseases caused by, for example, Corticium species, such as Corticium graminearum; Fusarium species, such as Fusarium oxysporum; Gaeumannomyces species, such as Gaeumannomyces graminis; Plasmodiophora species, such as Plasmodiophora brassicae; Rhizoctonia species, such as Rhizoctonia solani; Sarocladium species, such as Sarocladium oryzae; Sclerotium species, such as Sarocladium oryzae; Tapesia species, such as Tapesia aquaformis; acuformis); Thielaviopsis species, e.g., Thielaviopsis basicola; Ganoderma species, e.g., Ganoderma lucidum; Diseases of ears (including corn cobs) caused by, for example, Alternaria spp., for example Alternaria spp.; Aspergillus spp., for example Aspergillus flavus; Cladosporium spp., for example Cladosporium cladosporioides; Claviceps spp., for example Claviceps purpurea; Fusarium spp., for example Fusarium culmorum; Gibberella spp., for example Gibberella zeae; Monographera spp., for example Monographella nivalis; Stagnospora spp., for example Stagnospora nodoru; Diseases caused by the following smut fungi, for example Sphacelotheca species, for example Sphacelotheca reiliana; Tilletia species, for example Tilletia caries or Tilletia controversa; Urocystis species, for example Urocystis occulta; Ustilago species, for example Ustilago nuda; Fruit rot caused by, for example, Aspergillus species, for example Aspergillus flavus; Botrytis species, for example Botrytis cinerea; Penicillium species, for example Penicillium expansum or Penicillium purpurogenum; Rhizopus species, for example Rhizopus stolonifer; Sclerotinia species, for example Sclerotinia sclerotiorum; Verticillium species, for example Verticillium alboatrum; Seed and soil borne rot and wilt diseases as well as seedling diseases caused by, for example, Alternaria species, for example Alternaria brassicicola; Aphanomyces species, for example Aphanomyces euteiches; Ascochyta species, for example Ascochyta lentis; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium herbarum; herbarum; Cochliobolus species, for example Cochliobolus sativus (conidiomorph: Drexlera, Bipolaris syn.: Helminthosporium); Colletotrichum species, for example Colletotrichum coccodes; Fusarium species, for example Fusarium curmorum; Gibberella species, for example Gibberella zeae; Macrohomina species, for example Macrohomina phaseolina; Microdochium species, for example Microdochium nivale; Monogramfera species, for example Monogramfera nivalis; Penicillium species, for example Penicillium expansum; Poma species, for example Phoma lingam lingam);Homapsis species, for example, Phomopsis sojae;Phytophthora species, for example, Phytophthora cactorum;Pleospora species, for example, Pyrenophora graminea;Pyricularia species, for example, Pyricularia oryzae;Pythium species, for example, Pythium ultimum;Rhizoctonia species, for example, Rhizoctonia solani;Rhizopus species, for example, Rhizopus oryzae;Sclerotium species, for example, Sclerotium rolfsii;Septoria species, for example, Septoria nodorum; Typhula species, for example, Typhula incarnata; Verticillium species, for example, Verticillium dahliae; Canker, gall and witches' broom diseases caused by, for example, Nectria species, e.g. Nectria galligena; Wilt diseases caused by, for example, Monilinia species, e.g. Monilinia laxa; Malformations of leaves, flowers and fruits caused by, for example, Exobasidium species, e.g., Exobasidium vexans; Taphrina species, e.g., Taphrina deformans; debilitating diseases of woody plants caused by, for example, Esca species, such as Phaemoniella clamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea; Ganoderma species, such as Ganoderma boninense; Flower and seed diseases caused by, for example, Botrytis species, e.g. Botrytis cinerea; Diseases of plant tubers caused by, for example, Rhizoctonia species, e.g., Rhizoctonia solani; Helminthosporium species, e.g., Helminthosporium solani; Diseases caused by the following bacterial pathogens, for example: Xanthomonas species, for example, Xanthomonas campestris pv. oryzae; Pseudomonas species, for example, Pseudomonas syringae pv. lachrymans; Erwinia species, for example, Erwinia amylovora; Ralstonia species, for example, Ralstonia solanacearum; Fungal diseases of the roots and stem bases caused by, for example, black root rot (Calonectria crotalariae), anthracnose (Macrophomina phaseolina), Fusarium wilt or Fusarium wilt, root rot and sheath and root rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus root rot (Mycoleptodiscus terrestris), Neocosmospora (Neocosmospora basinfecta), vasinfecta), sheath and stem blight (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var. caulivora), Phytophthora rot (Phytophthora megasperma), leaf drop (Phialophora gregata), Pythium rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum ultimum), Rhizoctonia root rot, stem rot and damping off (Rhizoctonia solani), Sclerotinia stem rot (Sclerotinia sclerotiorum), Sclerotinia southern blight (Sclerotinia rolfsii), Thielaviopsis root rot (Thielaviopsis basicola).

[0143] Plants that can be treated according to the invention include the following: Rosaceae (e.g. pome fruits such as apple, pear, apricot, cherry, almond and peach), Libesioidae, Juglandaceae, Birch, Anacardiaceae, Fagaceae, Mulberry, Oleaceae, Actinidiaceae, Lauraceae, Musaceae (e.g. banana trees and plantation plants), Rubiaceae (e.g. coffee), Tulips, and the like. Plants of the family Celastraceae, Brassicaceae, Rutaceae (e.g., lemons, oranges, and grapefruit); Plants of the family Vitaceae (e.g., grapes); Plants of the family Solanaceae (e.g., tomatoes, peppers), Plants of the family Lilies, Plants of the family Asteraceae (e.g., lettuce), Plants of the family Apiaceae, Plants of the family Cruciferae, Plants of the family Chenopodiaceae, Plants of the family Cucurbitaceae (e.g., cucumbers), Plants of the family Allium celastraceae (e.g., leeks, onions), Plants of the family Fabaceae (e.g., peas); Plants of the family Poaceae Major crop plants such as Gramineae sp. / Gramineae (e.g., maize, turfgrass, cereals (wheat, rye, rice, barley, oats, millet, and triticale), Asteraceae (e.g., sunflower), Brassicas (e.g., white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, bok choy, kohlrabi, radishes, and rapeseed, mustard, horseradish, and cress), Fabasae (e.g., beans, peanuts), Papilionaceae (e.g., soybeans), Solanaceae (e.g., potatoes), Chenopodiaceae (e.g., sugar beet, fodder beet, Swiss chard, beet root); Mallow (e.g., cotton); useful and ornamental plants for gardens and woodlands; and genetically modified varieties of each of these plants.

[0144] All plants and plant parts can be treated according to the invention. Plants are understood here to mean all plants and plant populations, such as desirable and undesirable wild plants or crop plants (including natural crop plants). Crop plants can be plants that can be obtained by conventional breeding and optimization methods, or by biotechnological and genetic engineering methods or a combination of these methods, including transgenic plants, and including plant cultivars that can and cannot be protected by plant breeder's rights. Plant parts are understood to mean all parts and organs of plants above and below ground, such as shoots, leaves, flowers and roots, examples of which include leaves, needles, stalks, stems, leaves, fruit bodies, fruits and seeds, as well as roots, tubers and rhizomes. Plant parts also include harvested material, as well as vegetative and reproductive propagation material, such as cuttings, tubers, rhizomes, scions and seeds.

[0145] The present invention further comprises the method of treating seeds, in particular the seeds (dormant, primed, pre-emerged, or even when roots and leaves emerge) treated with at least one compound of formula (I) and its composition.The seeds of the present invention are used in the method of protecting seeds and the plants that germinate from seeds from phytopathogenic harmful fungi.These methods use the seeds treated with at least one active ingredient of the present invention.

[0146] It is also desirable to optimize the amount of active ingredient used so that the seed, germinating plants and germinating seedlings are protected from attack by phytopathogens as best possible, while the plant itself is not damaged by the active ingredient used.In particular, the seed treatment method should also take into account the specific phenotype of transgenic plants, so as to minimize the use of crop protection compositions and provide optimal protection for the seed and germinating plants.

[0147] Therefore, the present invention also relates to a method for protecting seeds, germinating plants and emerging seedlings from attack by animal pests and / or phytopathogenic harmful microorganisms by treating the seeds with the composition of the present invention.The present invention also relates to the use of the composition according to the present invention for treating seeds to protect the seeds, germinating plants and emerging seedlings from animal pests and / or phytopathogenic microorganisms.The present invention further relates to seeds treated with the composition of the present invention for protection against animal pests and / or phytopathogenic microorganisms.

[0148] One of the advantages of the present invention is that the treatment of seeds with these compositions protects not only the seeds themselves but also the plants obtained after emergence from animal pests and / or phytopathogenic harmful microorganisms.In this way, plants are protected by immediate treatment of crops at or shortly after sowing and by seed treatment before sowing.The active ingredient or composition of the present invention can also be used, inter alia, for transgenic seeds, in which case the advantage is also conceivable that the plants grown from these seeds can express proteins that act against pests, herbicide damage or abiotic stress.The treatment of such seeds with the active ingredient or composition of the present invention, for example insecticidal proteins, can result in the control of certain pests.Surprisingly, further synergistic effects can be observed in this case, which further increases the effectiveness of protection against attack by pests, microorganisms, weeds or abiotic stress.

[0149] The compounds of formula (I) are suitable for the protection of the seeds of any plant variety used in agriculture, greenhouses, forestry or horticulture.More specifically, the seeds refer to the seeds of cereals (such as wheat, barley, rye, millet and oats), rapeseed, maize, cotton, soybean, rice, potato, sunflower, bean, coffee, beet (such as sugar beet and fodder beet), peanut, vegetables (such as tomato, cucumber, onion and lettuce), turf and ornamental plants.The treatment of the seeds of wheat, soybean, rapeseed, maize and rice is particularly important.

[0150] As also described below, the treatment of transgenic seeds with the active ingredients or compositions of the present invention is particularly important. Transgenic seeds refer to the seeds of plants that contain at least one heterologous gene, which allows the expression of a polypeptide or protein with, for example, insecticidal properties. Such heterologous genes in transgenic seeds can be derived from microorganisms of, for example, the species of Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. These heterologous genes are preferably derived from species of the genus Bacillus, in which case the gene product is effective against the European corn borer and / or the Western corn rootworm. In particular, preferably, the heterologous genes are derived from Bacillus thuringiensis.

[0151] In the context of the present invention, the composition of the present invention is applied either alone or in a suitable formulation.Preferably, the seed is treated in a sufficiently stable state so that no damage occurs during the process of treatment.Generally, the seed can be treated at any time between harvesting and a certain time after sowing.It is customary to use the seed separated from the plant and the seed removed from the fruit cob, husk, stalk, skin, hair or flesh.For example, it is possible to use the seed that is harvested, washed and dried to a moisture content of less than 15% by weight.Alternatively, it is also possible to use the seed that is treated after drying, for example with water, and then dried again, or the seed immediately after priming, or the seed that is stored under priming conditions, or the seed after pre-germination, or the seed that is sown on a seedbed tray, tape or paper.

[0152] When treating seeds, it must be ensured that the amount of the composition of the invention and / or the amount of further additives applied to the seeds is selected so as not to cause harm to the germination of the seeds or to cause damage to the plants obtained.This must be ensured especially in the case of active ingredients that may show phytotoxic effects at certain application rates.

[0153] The compound of formula (I) can be applied directly, i.e., it does not contain any other components and is not diluted.Generally, it is preferred to apply the composition to seeds in the form of a suitable formulation.Suitable formulations and methods for seed treatment are known to those skilled in the art.The compound of formula (I) can be converted into a conventional formulation related to seed surface application, such as a solution, emulsion, suspension, dust, foam, slurry, or can be combined with other seed coating compositions, such as film-forming materials, pellet-forming materials, fine iron or other metal powders, granules, seed inactivating coating materials, and also ULV formulations.

[0154] In the treatment of seeds to facilitate planting, the seeds may be coated with a polymer. The polymer coating comprises a binder, a wax and a pigment, and one or more stabilizers in an amount effective to stabilize the suspension. 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 ether maleic anhydride, or butadiene styrene. Other similar polymers may also be used.

[0155] These formulations are prepared in known manner by mixing the active ingredient or combinations of active ingredients with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersing agents, emulsifiers, antifoaming agents, preservatives, secondary thickeners, adhesives, gibberellins and also water.

[0156] Useful dyes that can be present in the seed dressing formulations that can be used according to the invention are all dyes that are conventional for such purposes. Either water-soluble or water-soluble pigments can be used. Examples include the dyes known by the names Rhodamine B, CI Pigment Red 112 and CI Solvent Red 1.

[0157] Useful wetting agents that can be present in the seed dressing formulations that can be used according to the invention are all substances that promote wetting and are commonly used in the formulation of active pesticide ingredients. Alkylphthalenesulfonates, such as diisopropylnaphthalenesulfonate or diisobutylphthalenesulfonate, can be used preferentially.

[0158] Useful dispersants and / or emulsifiers that can be present in the seed dressing formulations that can be used according to the invention are all non-ionic, anionic and cationic dispersants that are customarily used in the formulation of active agrochemical ingredients. Non-ionic or anionic dispersants or mixtures of non-ionic or anionic dispersants can be preferentially used. Useful nonionic dispersants include, inter alia, ethylene oxide / propylene oxide block polymers, alkylphenol polyglycol ethers and tristyrylphenol polyglycol ethers, and their phosphorylated or sulfated derivatives. Suitable anionic dispersants are, inter alia, lignosulfonates, polyacrylates, and arylsulfonic acid / formaldehyde condensates.

[0159] Antifoaming agents that may be present in the seed dressing formulations that can be used according to the invention are all foam-inhibiting substances that are customarily used in the formulation of active agrochemical ingredients. Silicone antifoaming agents and magnesium stearate can be used preferentially.

[0160] Preservatives which may be present in the seed dressing formulations usable according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophene and benzyl alcohol hemiformal.

[0161] Secondary thickeners which may be present in the seed dressing formulations usable according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.

[0162] Adhesives that can be present in the seed dressing formulations that can be used according to the invention are all conventional binders that can be used in seed dressing products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

[0163] The formulations for seed surface application usable according to the invention can be used to treat a wide variety of seeds, either directly or after pre-dilution with water. For example, the concentrates, or preparations obtainable from the concentrates by dilution with water, can be used to dress cereal seeds such as wheat, barley, rye, oats and triticale, as well as maize, soybean, rice, rapeseed, pea, bean, cotton, sunflower and beet seeds, or a wide variety of vegetable seeds. The formulations usable according to the invention, or their diluted preparations, can also be used on the seeds of transgenic plants. In this case, additional synergistic effects may also occur upon interaction with the substances formed by expression.

[0164] When treating seeds with the formulations that can be used according to the present invention or the preparations that are prepared from said formulations by adding water, all mixing units that can be used for seed surface application are useful.Specifically, the procedure for seed surface application is to put seeds into a mixer, add a specific desired amount of formulation, either as is or after pre-dilution with water, and mix everything until all applied formulations are uniformly distributed on the seed surface.If appropriate, this is followed by a drying operation.

[0165] The application rate of the formulations usable according to the invention can vary within a relatively wide range.The application rate is guided by the specific content of active ingredients in the formulation and by the seed.The application rate of each single active ingredient is generally between 0.001 and 15 g per kilogram of seed, preferably between 0.01 and 5 g per kilogram of seed.

[0166] When using the compounds of formula (I) as fungicides, the application rates can vary within a relatively wide range, depending on the type of application. The application rates of the active ingredients according to the invention are as follows: For the treatment of plant parts, e.g. leaves: 0.1 to 10 000 g / ha, preferably 10 to 1 000 g / ha, more preferably 30 to 300 g / ha (when applied by watering or dripping it is even possible to reduce the application rate, especially when using inert substrates such as rock wool or perlite); For 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; For soil treatment: 0.1 to 10,000 g / ha, preferably 1 to 5,000 g / ha It is.

[0167] These application rates are merely examples and are not limiting for the purposes of the present invention.

[0168] In some cases, the compounds of formula (I) may also be used, at certain concentrations or application rates, as herbicides, safeners, growth regulators, or agents for improving plant properties, or as microbicides, for example as fungicides, antifungals, bactericides, antiviral agents (including compositions against viroids), or as compositions against MLOs (mycoplasma-like organisms) and RLOs (rickettsia-like organisms).

[0169] The compounds of formula (I) interfere with the physiological processes of plants and may therefore also be used as plant growth regulators. Plant growth regulators can exert various effects on plants.The effect of this substance essentially depends on the development stage of the plant, the application time with respect to the plant variety, and also on the amount of active ingredient applied to the plant or its environment, and the type of application.In each case, the growth regulator should have a specific desired effect on crop plants.

[0170] The growth regulating effects are earlier germination, better emergence, more developed root system and / or improved root growth, improved tillering ability, more effective tillers, earlier flowering, increased plant length and / or biomass, shorter stems, improved shoot growth, number of kernels / panicles, number of panicles / m 2 These include number of shoots, number of stalks and / or number of flowers, increased harvest index, larger leaves, reduced basal leaves, improved phyllotaxy, early maturity / early fruit set, uniform ripening, increased ripening period, better fruit set, larger fruit / vegetable size, reduced sprouting resistance and lodging.

[0171] The increase or improvement in yield may be measured by measuring total biomass per hectare, yield per hectare, kernel / fruit weight, seed size and / or hectoliter weight, as well as the following: Improved processability in terms of size distribution (kernel, fruit, etc.), uniform ripening, grain moisture, better milling, better brewing, better brewing, increased juice yield, harvestability, digestibility, sedimentation value, falling number, pod stability, storage stability, improved fibre length / strength / homogeneity, improved milk and / or meat quality in silage-raised animals, suitability for cooking and frying. further including improved fruit / grain quality, size distribution (kernel, fruit, etc.), improved storage / shelf life, improved marketability related to elasticity / softness, taste (aroma, texture, etc.), grade (size, shape, number of berries, etc.), number of berries / fruits per bunch, crispness, freshness, amount of wax coverage, frequency of physiological injuries, color, etc.; Further, the present invention further includes an increase in desired components such as protein content, fatty acids, oil content, oil quality, amino acid composition, sugar content, acid content (pH), sugar / acid ratio (Brix meter), polyphenols, starch content, nutritional quality, gluten content / index, energy content, taste, etc. Further reductions in undesirable components such as, for example, less mycotoxins, less aflatoxins, geosmin levels, phenolic aroma, laccase, polyphenol oxidase and peroxidase, nitrate content, etc. Refers to improving the quality of products.

[0172] Plant growth regulating compounds can be used, for example, to slow down the vegetative growth of plants.Thus, such growth slowdown is of economic interest, for example, in the case of grass, because it can reduce the frequency of mowing in ornamental gardens, parks and sports facilities, roadsides, airports, or in fruit crops.Similarly important is the suppression of the growth of herbaceous and woody plants on roadsides and near pipelines or overhead cables, or very generally in areas where vigorous plant growth is not desired.

[0173] Similarly, the use of growth regulators is important because they inhibit the longitudinal growth of cereals. This reduces or completely eliminates the risk of lodging of the plants before harvest. Furthermore, growth regulators in the case of cereals can strengthen the culms which also prevent lodging. The use of growth regulators to shorten and strengthen the culms allows for greater fertilizer application to increase yields without any risk of lodging of the cereal crop.

[0174] In many crop plants, the reduction in vegetative growth allows for denser plantings and therefore higher yields to be achieved based on the soil surface. Another advantage of the smaller plants obtained in this way is that the crop is easier to grow and harvest.

[0175] Reduction in vegetative plant growth can also result in increased and improved yields since nutrients and assimilates are more beneficial to flower and fruit formation than to the vegetative parts of the plant.

[0176] Alternatively, growth regulators can also be used to promote vegetative growth, which has great benefits when harvesting vegetative plant parts, but promoting vegetative growth can also promote reproductive growth, where additional assimilates are formed, resulting in more or larger fruits.

[0177] Furthermore, beneficial effects on growth or yield can be achieved through improved nutrient use efficiency, especially nitrogen (N) use efficiency, phosphorus (P) use efficiency, water use efficiency, improved transpiration, respiration and / or CO2 assimilation rates, better nodulation, improved Ca metabolism, etc.

[0178] Similarly, growth regulators can be used to modify the composition of plants, which can then lead to improved quality of harvested products. Under the influence of growth regulators, parthenocarpic fruits can be formed. In addition, the sex of flowers can be influenced. It is also possible to produce sterile pollen, which is very important in the breeding and production of hybrid seeds.

[0179] The use of growth regulators can control the branching of plants. On the other hand, it is possible to promote the growth of lateral shoots by breaking apical dominance, which, also in combination with growth inhibition, can be very desirable, especially in the cultivation of ornamental plants. On the other hand, it is also possible to inhibit the growth of lateral shoots. This effect is of particular interest, for example, in the cultivation of tobacco or in the cultivation of tomatoes.

[0180] Under the influence of growth regulators, the amount of leaves on the plant can be controlled so that the plant defoliates at the desired time. Such defoliation plays a major role in the mechanical harvesting of cotton, but is also of interest in other crops, such as viticulture, to facilitate harvesting. Defoliation of plants can also be carried out to reduce the transpiration of the plant before it is transplanted.

[0181] Additionally, growth regulators can modulate plant senescence, which may increase the duration of green leaf area, prolong the grain filling period, and improve yield quality.

[0182] Similarly, growth regulators can be used to regulate fruit dehiscence. On the one hand, it is possible to prevent premature fruit dehiscence. On the other hand, it is also possible to promote fruit dehiscence or even deflowering ("deflowering") to achieve a desired mass. Furthermore, growth regulators can be used at harvest to reduce the force required to cut the fruit, to allow mechanical harvesting or to facilitate manual harvesting.

[0183] Growth regulators can also be used to achieve faster or slower maturation of harvested material before or after harvest. This is particularly advantageous, since it allows optimal adjustment to market requirements. Furthermore, growth regulators can improve fruit color in some cases. Furthermore, growth regulators can also be used to synchronize maturation within a certain period of time, which establishes the necessary conditions for completing mechanical or manual harvesting in a single operation, for example in the case of tobacco, tomatoes or coffee.

[0184] By using growth regulators, it is further possible to affect the dormancy of plant seeds or sprouts, so that plants such as pineapples or nursery ornamentals, for example, sprout, emerge or flower at a time when they would not normally be inclined to do so. In areas at risk of frost, it may be desirable to delay seed emergence or germination with the aid of growth regulators in order to avoid damage caused by late frosts.

[0185] Finally, growth regulators can induce resistance in plants to frost, drought or high salinity in the soil, which allows the cultivation of plants in areas that are not normally suitable for this purpose.

[0186] The compounds of formula (I) also show a strong enhancing effect in plants and can therefore be used to mobilize the defense of plants against attack by unwanted microorganisms.

[0187] A plant-enhancing (resistance-inducing) substance in this context is a substance capable of stimulating the plant's defense system so that, when the treated plant is subsequently inoculated with undesirable microorganisms, it develops a high degree of resistance to these microorganisms.

[0188] Furthermore, in the context of the present invention, the plant physiological effects of the present invention include the following: high or low temperature tolerance, drought tolerance and recovery after drought stress, water use efficiency (related to reduced water consumption), flood tolerance, ozone stress and UV tolerance, abiotic stress tolerance including tolerance to chemicals such as heavy metals, salts, pesticides, etc.

[0189] Biotic stress resistance, including improved resistance to fungi and improved resistance to nematodes, viruses and bacteria. In the context of the present invention, biotic resistance preferably includes improved resistance to fungi and improved resistance to nematodes.

[0190] Increased plant vigour including plant health / plant quality and seed vigour, reduced stand defects, improved appearance, enhanced recovery after periods of stress, improved pigmentation (e.g. chlorophyll content, stay-green effect etc.) and improved photosynthetic efficiency.

[0191] Furthermore, the compounds of formula (I) are capable of reducing the mycotoxin content in harvested material and in foods and feeds prepared therefrom. Mycotoxins include in particular, but not exclusively, the following; deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2- and HT2-toxins, fumonisins, zearalenone, moniliformin, fusarin, diaceotoxicirpenol (DAS), beauvericin, enniatins, fusaroproliferin, fusarenol, ochratoxin, patulin, ergot alkaloids and aflatoxins, which are found, for example, in the fungi F. acuminatum, F. asiaticum, F. avenaceum, F. crookwellense, F. curmorum, F. graminearum (Gibberella zeae), F. arginata, ... zeae), F. equiseti, F. fujikoroi, F. musarum, F. oxysporum, F. proliferatum, F. poae, F. pseudograminearum, F. sambucinum, F. scirpi, F. semitectum, F. solani, F. sporotrichoides, F. langsetiae by Fusarium species such as F. langsethiae, F. subglutinans, F. tricinctum, F. verticillioides, and also by Aspergillus species such as A. flavus, A. parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, P. vercosum ...verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, P. roqueforti, and other Penicillium species; Claviceps species such as C. purpurea, C. fusiformis, C. paspali, C. africana, and other Stachybotrys species.

[0192] The compounds of formula (I) may also be used in materials protection, for protecting industrial materials against attack and destruction by phytopathogenic fungi.

[0193] Additionally, the compounds of formula (I) can be used alone or in combination with other active ingredients as antifouling compositions.

[0194] Industrial materials in this context are understood to mean inanimate materials prepared for use in industry.For example, the industrial materials to be protected by the composition of the present invention from microbial degradation or destruction can be adhesives, glues, paper, wallpaper and cardboard / cardboard, textiles, carpets, leather, wood, textiles and tissues, paints and plastic articles, cooling lubricants, and other materials that may be infected or destroyed by microorganisms.Parts of manufacturing plants and buildings that may be damaged by microbial growth, such as cooling water circuits, cooling and heating systems, and ventilation and air conditioning units, can be mentioned within the scope of the materials to be protected.Industrial materials within the scope of the present invention preferably include adhesives, sizing agents, paper and cardboard, leather, wood, paints, cooling lubricants, and heat transfer fluids, more preferably wood.

[0195] The compounds of formula (I) are capable of preventing deleterious effects such as decay, spoilage, discolouration, bleaching or mould formation.

[0196] When treating wood, the compound of formula (I) can also be used against fungal diseases that tend to grow on or inside wood.The term "wood" refers to all types of wood species and all types of such wood products for construction, such as solid wood, high density wood, laminated wood and plywood.The method of treating wood according to the present invention mainly consists in contacting the composition according to the present invention.This includes, for example, direct application, spraying, immersion, injection, or any other suitable means.

[0197] Furthermore, the compounds of formula (I) can be used to protect objects in contact with seawater or brackish water from fouling, especially ship hulls, covers, nets, structures, mooring rigging and signalling systems.

[0198] The compounds of formula (I) can also be used to protect stored goods, which are understood to mean natural substances of vegetable or animal origin or their processed products of natural origin, for which long-term protection is desired.

[0199] Storage products of plant origin, such as plants or plant parts, such as stems, leaves, tubers, seeds, fruits, grains, etc., can be protected in the freshly harvested state or after being processed by (pre)drying, moistening, crushing, grinding, pressing or roasting.Storage products also include both unprocessed wood, such as building timber, utility poles and fences, or wood in the form of finished products, such as furniture.Storage products of animal origin are, for example, hides, leather, furs and animal hair.The composition of the present invention can prevent harmful effects such as decay, rotting, discoloration, bleaching or mold formation.

[0200] Microorganisms capable of deteriorating or degenerating industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms. The compounds of formula (I) preferably act against fungi, especially molds, wood-discoloring fungi and wood-destroying fungi (Ascomycetes, Basidiomycetes, Deuteromycetes and Zygomycetes), as well as slime organisms and algae. Examples include microorganisms of the following genera: 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 piciophylla). pityophila, etc.); Trichoderma (Trichoderma viride, etc.); Ophiostoma spp., Ceratocystis spp., Humicola spp., Petriella spp., Triculus spp., Coriolus spp., Gloeophyllum spp., Pleurotus spp., Polya spp., Serpula spp., and Chiromyces spp., Cladosporium spp., Paecilomyces spp., Mucor spp., Escherichia (Escherichia coli, etc.); Pseudomonas (Pseudomonas aeruginosa, etc.); Staphylococcus (Staphylococcus aureus, etc.); aureus), Candida species, and Saccharomyces species (e.g., Saccharomyces cerevisae).

[0201] Moreover, the compounds of formula (I) also have very good antifungal action. They have a very wide spectrum of antifungal activity, especially against dermatophytes and yeasts, molds and dimorphic fungi (e.g. Candida species such as Candida albicans, Candida glabrata), and Aspergillus species such as Epidermophyton floccosum, Aspergillus niger and Aspergillus fumigatus, Triclophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and Microsporon audouinii. The listing of these fungi in no way constitutes a limitation of the spectrum of molds included, but is merely exemplary in nature.

[0202] The compounds can also be used to control important fungal pathogens in fish and shellfish aquaculture, such as Saprolegnia diclina in trout and Saprolegnia parasitica in crayfish.

[0203] Thus, the compounds of formula (I) may be used in both medical and non-medical applications.

[0204] The compounds of formula (I) can be used as they are, or in the form of their preparations, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules, or in the use forms prepared from the form of their preparations. Application is carried out in a conventional manner, for example by watering, spraying, misting, general application, dusting, dusting, foaming, surface application, etc. It is also possible to spread the active ingredient by ultra-low-volume method, or to inject the active ingredient preparation / active ingredient itself into the soil. It is also possible to treat the seeds of plants.

[0205] Preferably, wild plant species and plant cultivars, or those obtained by conventional biological breeding methods such as crossing or protoplast fusion, and also parts thereof, can be treated with all plants and their parts according to the invention. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering methods, where appropriate in combination with conventional methods (genetically modified organisms) and their parts, are treated. The terms "parts" or "plant parts" or "plant parts" are explained above. More preferably, plants of plant cultivars that are commercially available or in use are treated according to the invention. Plant cultivars are understood to mean plants that have new properties ("traits") and that are obtained by conventional breeding, by mutagenesis or recombinant DNA techniques. They can be cultivars, varieties, biotypes or genotypes.

[0206] The treatment method according to the invention can be used for the treatment of genetically modified organisms (GMOs), for example plants or seeds. A genetically modified plant (or transgenic plant) is a plant in which a heterologous gene is stably integrated into the genome. The expression "heterologous gene" essentially means a gene presented or constructed outside the plant, which, when introduced into the nuclear, chloroplast or mitochondrial genome, confers new or improved agronomic or other properties to the transformed plant by expressing a protein or polypeptide of interest or by down-regulating or silencing other gene(s) present in the plant (for example using antisense, cosuppression, RNA interference-RNAi- or microRNA-miRNA-technologies). A heterologous gene located in the genome is also called a transgene. A transgene defined by its specific location in the plant genome is called a transformation or transgenic event.

[0207] Plants and plant cultivars which are preferably treated according to the invention include all plants (whether obtained by breeding and / or biotechnological means) which have genetic material that confers particularly advantageous and useful traits to these plants.

[0208] Plants and plant cultivars which are preferably also treated according to the invention are tolerant to one or more biotic stresses, i.e. they exhibit good protection against animals and harmful microorganisms, such as nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and / or viroids.

[0209] Plants and plant cultivars that can also be treated according to the present invention are plants that are tolerant to one or more abiotic stresses.Abiotic stress conditions include, for example, drought, exposure to low temperatures, exposure to heat, osmotic stress, waterlogging, increased salinity in the soil, increased exposure to minerals, exposure to ozone, exposure to strong light, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, and shade avoidance.

[0210] Plants and plant cultivars that can also be treated according to the present invention are plants that are characterized by the feature of increased yield. The increased yield in said plants can be the result of improved plant physiology, growth and development, such as, for example, water use efficiency, water retention efficiency, improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, improved germination efficiency and accelerated maturation. Yield can further be affected by improved plant architecture, including, but not limited to, early flowering, flowering control for hybrid seed production, seedling vigor, plant size, number and distance of internodes, root growth, seed size, fruit size, pod size, number of pods or ears, number of seeds per pod or ear, seed mass, enhanced seed ripening, reduced seed dispersal, reduced pod dehiscence and reduced lodging resistance (under stress and non-stress conditions). Further yield traits include seed composition such as carbohydrate content and composition, e.g. cotton or starch, protein content, oil content and composition, nutritional value, reduced anti-nutritional compounds, improved processability, and good storage stability.

[0211] The plants that can be treated according to the invention are generally hybrid plants that already exhibit the characteristics of heterosis, i.e. hybrid vigor, which results in higher yields, higher vigor, higher health and higher resistance to biotic and abiotic stresses.

[0212] The plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can be treated according to the present invention are herbicide-resistant plants, i.e. plants that have been made tolerant to one or more given herbicides. Such plants can be obtained by genetic transformation or by selecting plants that contain a mutation that confers such herbicide resistance.

[0213] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can be treated according to the invention are insect-resistant transgenic plants, i.e. plants that are made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation or by selecting plants that contain mutations that confer such insect resistance.

[0214] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can be treated according to the invention are tolerant to abiotic stresses. Such plants can be obtained by genetic transformation or by selecting plants containing mutations that confer such stress tolerance.

[0215] Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can be treated according to the invention exhibit alterations in the quantity, quality and / or storage stability of the harvested product and / or alterations in the characteristics of certain components of the harvested product.

[0216] Plants or plant cultivars (obtainable by plant biotechnology methods such as genetic engineering) that can be treated according to the invention are plants with modified fiber characteristics, such as cotton plants. Such plants can be obtained by genetic transformation or by selecting plants containing mutations that confer such modified fiber characteristics.

[0217] Plants or plant cultivars (which can be obtained by plant biotechnology methods such as genetic engineering) that can be treated according to the present invention are plants such as rapeseed plants or related Brassica plants, which have modified oil profile characteristics. Such plants can be obtained by genetic transformation or by selecting plants containing mutations that confer such modified oil profile characteristics.

[0218] Plants or plant cultivars (which can be obtained by plant biotechnology methods such as genetic engineering) that can be treated according to the present invention are plants such as rapeseed plants or related Brassica plants that have seed shattering characteristics. Such plants can be obtained by genetic transformation or by selecting plants that contain mutations that confer such seed shattering characteristics, and include plants such as rapeseed plants in which seed shattering is delayed or reduced.

[0219] Plants or plant cultivars (which may be obtained by plant biotechnology methods such as genetic engineering) which may be treated according to the invention are plants, such as tobacco plants, which have an altered post-translational protein modification pattern.

[0220] Thus, compounds of the present invention are exemplified in Tables 1 and 2.

[0221] The following table illustrates non-limiting examples of compounds according to the present invention. In the following examples, M+1 (or M-1) means the molecular ion peak plus or minus 1 a.mu (atomic mass unit), respectively, as observed by mass spectrometry. The "H-NMR data for selected examples is 1 The information is provided in the form of a H-NMR peak list. For each signal peak, the δ value in ppm and the number of protons in parentheses are listed.

[0222] 1 To calibrate the chemical shifts for H spectra, we use the chemical shifts of tetramethylsilane and / or the solvent used, especially for spectra measured in DMSO. Thus, in the NMR peak list, tetramethylsilane peaks may, but do not necessarily, occur.

[0223] 1 The H-NMR peak list is a standard 1 It resembles a 1 H-NMR print and therefore contains all 15 peaks normally listed in a standard NMR interpretation.

[0224] Moreover, the peaks are similar to those of the solvent standard. ’ 1 H-NMR prints may show the stereoisomers of the target compound of the present invention and / or peaks of impurities.

[0225] Table 1 presents compounds of general formula (I). [ka]

[0226] [Table 1]

[0227] [Table 2]

[0228] [Table 3]

[0229] [Table 4]

[0230] [Table 5]

[0231] [Table 6]

[0232] [Table 7]

[0233] [Table 8]

[0234]

Table 9

[0235]

Table 10

[0236]

Table 11

[0237]

Table 12

[0238]

Table 13

[0239]

Table 14

[0240]

Table 15

[0241]

Table 16

[0242]

Table 17

[0243]

Table 18

[0244] [Table 19]

[0245] [Table 20]

[0246] [Table 21]

[0247] [Table 22]

[0248] [Table 23]

[0249] [Table 24]

[0250] [Table 25]

[0251] [Table 26]

[0252] [Table 27]

[0253] Table 2 shows the R x , R y , R 4 , R 5 , R 6 , R 7 , R 8 , R 9and A is defined as follows: [ka]

[0254] [Table 28]

[0255] [Table 29]

[0256] The compounds of the invention as defined by general formula (I) and / or in Tables 1 and 2 can be prepared in a variety of ways as known in the art and as described in Schemes 1 to 4. [ka]

[0257] Compounds of formula 1a can be prepared by treating compounds of formula 3 with trimethyl orthoformate followed by cleavage with various secondary amines (HNR 1 R 2 ) can be synthesized by reaction with

[0258] Compound 1 is a key intermediate in the synthesis of compounds of formula 1a. Various methods have been described in the literature for the synthesis of compounds of formula 1, such as: Method 1: From the corresponding benzoyl chloride using the catalyst ZnCl2 or AlCl3 in the presence of dichloromethane, as described in Helvitachimica Act XXIX (1946), pp. 1413-1424 and Tetrahedron, vol. 56 (2000), pp. 7199-7203.

[0259] Method 2: (a) from trifluoromethanesulfonic acid, as described in Tetrahedron, vol. 56 (2000), pp. 7199-7203; (b) from graphite and methanesulfonic acid, as described in Synthesis, vol. 13 (2004), pp. 2165-2168; (c) from graphite and p-toluenesulfonic acid, as described in Helvetiva Chimica act, vol. 88 (2005), pp. 2282-2287; (d) from the corresponding benzoic acid in the presence of an acid catalyst such as 1-perfluorobutanesulfonic acid, as described in Synthesis, vol. 10 (2000), pp. 1427-1430.

[0260] Method 3: From the corresponding derivative of benzoic acid in the presence of a metal salt of trifluoromethanesulfonate such as copper trifluoromethanesulfonate, gallium trifluoromethanesulfonate, antimony trifluoromethanesulfonate, ytterbium trifluoromethanesulfonate, scandium trifluoromethanesulfonate, or bismuth trifluoromethanesulfonate, as described in Green Chemistry, Vol. 4 (2002), pp. 129-133, or Tetrahedron, Vol. 56 (2000), pp. 663-6465, or Bull Chemical Society of Jpn, Vol. 73 (2000), pp. 2325-2333.

[0261] Method 4: From the corresponding substituted benzoic acids in the presence of P2O5 either as such or adsorbed on silica gel, as described in Tetrahedron letters vol. 49 (2008), pp. 6715-6719. [ka]

[0262] Compounds of formula 1a can be synthesized using appropriately substituted 2a according to the same method as described in Scheme 1. The corresponding intermediate 2a can be synthesized from phenylacetonitrile in the presence of a base such as sodium hydroxide or sodium tert.butoxide or sodium hydride, followed by oxidation with H2O2 / mCPBA in the presence of aqueous KOH, as described in (J.Org.Chem. 1983, vol. 48, pp. 4097-98; J.Org.Chem. 1983, vol. 48, pp. 4087-4096). [ka]

[0263] Compounds of formula 1a can also be synthesized using the Suzuki reaction by treating compounds of formula 6 with the corresponding substituted benzyl halide as described in Bioorganic & Medicinal Chemistry Letters, Vol. 14(No. 4), pp. 1023-1026; 2004.

[0264] Compounds of formula 6 can be synthesized in good yields by treating the bromo derivative 5 with bis(pincolato)diborane using palladium acetate and PdCl2(dppf)DCM complex in dioxane. [ka]

[0265] Compounds of formula 1 can be synthesized by treating a phenylboronic acid derivative having formula 7 with a compound of formula 8 (X is an activated form of a carboxylic acid, e.g., a chloride, and Y represents a precursor of an amine group, such as a nitro group or a NHCOCH3 group) in the presence of a base such as sodium carbonate, a palladium-based catalyst, and a surfactant such as sodium dodecyl sulfate, as described in Synthesis, Vol. 13, (2007), pp. 1970-1980.

[0266] The invention is further illustrated in the following non-limiting examples: The structures of the novel compounds were confirmed by NMR and / or other appropriate analyses as presented below. EXAMPLES

[0267] 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 To a suspension of N-(4-(3,5-dichlorobenzoyl)-2,5-dimethylphenyl)acetamide (0.9 g, 2.68 mmol) in dichloromethane (15 ml) was added triethylsilane (2.78 ml, 17.40 mmol) at 0° C. The reaction mixture was stirred for 10 minutes. Boron trifluoride etherate (2.090 g, 14.72 mmol) was added dropwise to the reaction mixture. The reaction mixture was stirred at room temperature for 36 hours. 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 phase was dried over anhydrous Na2SO4. The mixture was filtered and concentrated under reduced pressure. The residue was then purified by column chromatography on silica gel using hexane:ethyl acetate as eluent to give the desired N-(4-(3,5-dichlorobenzyl)-2,5-dimethylphenyl)acetamide (0.7 g) as a solid. LCMS (M+H) 323.23

[0268] 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) was charged sodium hydroxide (3.35 g, 84 mmol) 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 phase was dried over anhydrous Na2SO4. The mixture was then filtered and evaporated under reduced pressure. The residue was then purified by column chromatography on silica gel 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

[0269] 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-dimethylaniline (0.500 g, 1.784 mmol) in trimethyl orthoformate (10.00 ml) containing 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 dissolved in 1,4-dioxane (10 ml). N-ethylmethylamine (1.551 ml, 17.84 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 give a residue, which was then purified by column chromatography on silica gel using hexane:ethyl acetate as eluent to give 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, 1H-NMR(400MHz,DMSO-d6)δ7.61(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) EXAMPLES

[0270] 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 To a suspension of N-(4-(4-bromobenzoyl)-2,5-dimethylphenyl)acetamide (1.5 g, 4.33 mmol) in dichloromethane (30 ml) was added triethylsilane (3.02 g, 26.0 mmol) at 0° C. After stirring the reaction for 10 minutes, boron trifluoride etherate (3.69 g, 26.0 mmol) was added dropwise to the reaction mixture. After completion of the addition, the reaction mixture was stirred at room temperature for 36 hours. 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 phase was dried over anhydrous Na2SO4. The mixture was filtered and concentrated under reduced pressure. The mixture was then filtered and evaporated under reduced pressure. The residue was then purified by column chromatography on silica gel using hexane:ethyl acetate as eluent to give the desired N-(4-(4-bromobenzyl)-2,5-dimethylphenyl)acetamide (0.7 g) as a gum. LCMS (M+H) 333.24

[0271] 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 ethanol (21 ml)-water (9 ml) was charged potassium hydroxide (3.87 g, 69.0 mmol) 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 phase was dried over anhydrous Na2SO4. The mixture was then filtered and evaporated under reduced pressure. The residue was then purified by column chromatography on silica gel 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

[0272] Step C: Preparation of N'-(4-(4-bromobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide A solution of 4-(4-bromobenzyl)-2,5-dimethylaniline (0.4 g, 1.378 mmol) in trimethyl orthoformate (15.00 ml) containing 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 give an intermediate, which was then dissolved in 1,4-dioxane (15 ml). N-ethylmethylamine (1.198 ml, 13.78 mmol) was added and the reaction mixture was heated at 103° C. for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give a residue, which was then purified by column chromatography on silica gel using hexane:ethyl acetate as eluent to give the desired N'-(4-(4-bromobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide (0.4 g) as a gum. 1 H-NMR (400MHz, chloroform-D) δ7.42(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) EXAMPLES

[0273] 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 To a suspension of N-(4-(3,4-dichlorobenzoyl)-2,5-dimethylphenyl)acetamide (0.6 g, 1.785 mmol) in dichloromethane (30 ml) was added triethylsilane (1.245 g, 10.71 mmol) 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 completion of the addition, the reaction mixture was stirred at room temperature for 36 hours. 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 phase was dried over anhydrous Na2SO4. The mixture was filtered and concentrated under reduced pressure. The mixture was then filtered and evaporated under reduced pressure. The residue was then purified by column chromatography on silica gel using hexane:ethyl acetate as eluent to give the desired N-(4-(3,4-dichlorobenzyl)-2,5-dimethylphenyl)acetamide (0.4 g) as a gum. LCMS (M+H) 323.23

[0274] Step B: Preparation of 4-(3,4-dichlorobenzyl)-2,5-dimethylaniline To a suspension of (4-amino-2,5-dimethylphenyl)(3,4-dichlorophenyl)methanone (0.5 g, 1.700 mmol) in ethanol (10 ml)-water (3 ml) was charged potassium hydroxide (2.86 g, 51.0 mmol) 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 phase was dried over anhydrous Na2SO4. The mixture was then filtered and evaporated under reduced pressure. The residue was then purified by column chromatography on silica gel 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

[0275] 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-dimethylaniline (0.150 g, 0.535 mmol) in trimethyl orthoformate (10.00 ml) containing p-toluenesulfonic acid monohydrate (5.09 mg, 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 dissolved in 1,4-dioxane (10 ml). N-ethylmethylamine (0.465 ml, 5.35 mmol) was added and the reaction mixture was heated at 103° C. for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give a residue, which was then purified by column chromatography on silica gel using hexane:ethyl acetate as eluent to give the desired N'-(4-(3,4-dichlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide (0.13 g) as a gum. 1H-NMR(400MHz,DMSO-d6)δ7.60(bs,1H),7.52(d,1H),7.33(d,1H),7.09(dd,8.0Hz,1H),6.88(s,1H) ,6.57(s,1H),3.85(s,2H),3.48-3.30(bs,2H),2.91(s,3H),2.11(s,3H),2.07(s,3H),1.11(t,3H). EXAMPLES

[0276] N'-(2,5-dimethyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide Step A: N-(2,5-dimethyl-4-(3-methylbenzyl)phenyl)acetamide To a suspension of N-(2,5-dimethyl-4-(3-methylbenzoyl)phenyl)acetamide (1.5 g, 5.33 mmol) in dichloromethane (30 ml) was added triethylsilane (2.98 g, 25.6 mmol) at 0° C. After stirring for 10 minutes, boron trifluoride etherate (4.16 g, 29.3 mmol) was added dropwise to the reaction mixture. After completion of the addition, the reaction mixture was stirred at room temperature for 36 hours. 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 phase was dried over anhydrous Na2SO4. The mixture was filtered and concentrated under reduced pressure. The residue was then purified by column chromatography on silica gel using hexane:ethyl acetate as eluent to give the desired N-(2,5-dimethyl-4-(3-methylbenzyl)phenyl)acetamide (0.8 g) as a gum. LCMS (M+H) 268.37.

[0277] Step B: Preparation of 2,5-dimethyl-4-(3-methylbenzyl)aniline To a suspension of N-(2,5-dimethyl-4-(3-methylbenzyl)phenyl)acetamide (0.7 g, 2.62 mmol) in ethanol (21 ml)-water (9 ml) was charged potassium hydroxide (4.41 g, 79 mmol) 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 phase was dried over anhydrous Na2SO4. The mixture was then filtered and evaporated under reduced pressure. The residue was then purified by column chromatography on silica gel 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

[0278] 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) containing 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 dissolved in 1,4-dioxane (10 ml). N-ethylmethylamine (1.157 ml, 13.31 mmol) was added and the reaction mixture was heated at 103° C. for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give a residue, which was then purified by column chromatography on silica gel using hexane:ethyl acetate as eluent to give the desired N'-(2,5-dimethyl-4-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide (0.160 g) as a gum. 1H-NMR(400MHz,DMSO-d6)δ7.58(bs,1H),7.13(t,7.6Hz,1H),6.96(d,7.9Hz,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) EXAMPLES

[0279] N'-(4-(4-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide Step A: Preparation of N-(4-(4-chlorobenzyl)-2,5-dimethylphenyl)acetamide To a suspension of N-(4-(4-chlorobenzoyl)-2,5-dimethylphenyl)acetamide (1.8 g, 5.96 mmol) in dichloromethane (40 ml) was added triethylsilane (4.16 g, 35.8 mmol) 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 completion of the addition, the reaction mixture was stirred at room temperature for 36 hours. 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 phase was dried over anhydrous Na2SO4. The mixture was filtered and concentrated under reduced pressure. The mixture was then filtered and evaporated under reduced pressure. The residue was then purified by column chromatography on silica gel using hexane:ethyl acetate as eluent to give the desired N-(4-(4-chlorobenzyl)-2,5-dimethylphenyl)acetamide (1.5 g) as a solid. LCMS (M+H) 288.79.

[0280] 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 ethanol (21 ml)-water (9 ml) was charged potassium hydroxide (7.60 g, 136 mmol) 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 phase was dried over anhydrous Na2SO4. The mixture was then filtered and evaporated under reduced pressure. The residue was then purified by column chromatography on silica gel using hexane:ethyl acetate as eluent to give the desired 4-(4-chlorobenzyl)-2,5-dimethylaniline (0.8 g) as a solid. LCMS (M+H) 246.75

[0281] Step C: Preparation of N'-(4-(4-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide A solution of 4-(4-chlorobenzyl)-2,5-dimethylaniline (0.7 g, 2.85 mmol) in trimethyl orthoformate (10.00 ml) containing 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 dissolved in 1,4-dioxane (10 ml). N-ethylmethylamine (2.476 ml, 28.5 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 give a residue, which was then purified by column chromatography on silica gel using hexane:ethyl acetate as eluent to give the desired N'-(4-(4-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide (0.3 g) as a gum. 1H-NMR(400MHz,DMSO-d6)δ7.66-7.43(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) EXAMPLES

[0282] 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 To a suspension of N-(2,5-dimethyl-4-(4-(methylthio)benzoyl)phenyl)acetamide (1.7 g, 5.42 mmol) in dichloromethane (30 ml) was added triethylsilane (3.78 g, 32.5 mmol) at 0° C. After stirring the reaction for 10 minutes, boron trifluoride etherate (4.62 g, 32.5 mmol) was added dropwise to the reaction mixture. After completion of the addition, the reaction mixture was stirred at room temperature for 36 hours. 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 phase was dried over anhydrous Na2SO4. The mixture was filtered and concentrated under reduced pressure. The residue was then purified by column chromatography on silica gel using hexane:ethyl acetate as eluent to give the desired N-(2,5-dimethyl-4-(4-(methylthio)benzyl)phenyl)acetamide (0.7 g) as a gum. LCMS (M+H) 297.90

[0283] 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 ethanol (21 ml)-water (9 ml) was charged potassium hydroxide (3.93 g, 70.1 mmol) 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 phase was dried over anhydrous Na2SO4. The mixture was then filtered and evaporated under reduced pressure. The residue was then purified by column chromatography on silica gel 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

[0284] 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) containing p-toluenesulfonic acid monohydrate (0.011 g, 0.058 mmol) was stirred at 103° C. for 4 hours. The reaction mixture was concentrated under reduced pressure to give an intermediate, which was then dissolved in 1,4-dioxane (10.00 ml). N-ethylmethylamine (1.013 ml, 11.66 mmol) was added and the reaction mixture was heated at 103° C. for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give a residue, which was then purified by column chromatography on silica gel using hexane:ethyl acetate as eluent to give the desired N'-(2,5-dimethyl-4-(4-(methylthio)benzyl)phenyl)-N-ethyl-N-methylformimidamide (0.21 g) as a gum. 1H-NMR(400MHz,DMSO-d6)δ7.59-7.44(bs,1H),7.12(d,2H),7.01(d,2H),6.83-6.78(s,1H),6.51(s,1 H),3.75(s,2H),3.42-3.30(bs,2H),2.87(s,3H),2.39(s,3H),2.06(s,3H),2.05(s,3H),1.07(t,3H) EXAMPLES

[0285] 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 To a suspension of N-(2,5-dimethyl-4-(4-methylbenzoyl)phenyl)acetamide (1.4 g, 4.98 mmol) in dichloromethane (30 ml) was added triethylsilane (3.47 g, 29.9 mmol) 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. After completion of the addition, the reaction mixture was stirred at room temperature for 36 hours. 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 phase was dried over anhydrous Na2SO4. The mixture was filtered and concentrated under reduced pressure. The mixture was then filtered and evaporated under reduced pressure. The residue was then purified by column chromatography on silica gel using hexane:ethyl acetate as eluent to give the desired N-(2,5-dimethyl-4-(4-methylbenzyl)phenyl)acetamide (0.9 g) as a solid. LCMS (M+H) 268.37.

[0286] 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 ethanol (21 ml)-water (9 ml) was charged potassium hydroxide (4.41 g, 79 mmol) 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 phase was dried over anhydrous Na2SO4. The mixture was then filtered and evaporated under reduced pressure. The residue was then purified by column chromatography on silica gel 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

[0287] 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) containing 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 dissolved in 1,4-dioxane (10 ml). N-ethylmethylamine (1.157 ml, 13.31 mmol) was added and the reaction mixture was heated at 103° C. for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give a residue, which was then purified by column chromatography on silica gel using hexane:ethyl acetate as eluent to give the desired N'-(2,5-dimethyl-4-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide (0.160 g) as a gum. 1 H-NMR(400MHz,DMSO-d6)δ7.56(bs,1H),7.04(d,2H),6.97(d,2H),6.82(s,1H),6.53(s,1 H),3.79(s,2H),3.33(bs,2H),2.90(s,3H),2.23(s,3H),2.14-2.04(2s,6H),1.10(t,3H) EXAMPLES

[0288] N'-(2-bromo-4-(4-bromobenzyl)-3,6-dimethylphenyl)-N-ethyl-N-methylformimidamide Steps A and B were carried out as described in the above examples.

[0289] 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-dimethylaniline (0.5 g, 1.355 mmol) in trimethyl orthoformate (30.0 ml) containing 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 give an intermediate, which was then dissolved in 1,4-dioxane (30 ml). N-ethylmethylamine (1.178 ml, 13.55 mmol) was added and the reaction mixture was heated at 103° C. for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give a residue, which was then purified by column chromatography on silica gel using hexane:ethyl acetate as eluent to give the desired N'-(2-bromo-4-(4-bromobenzyl)-3,6-dimethylphenyl)-N-ethyl-N-methylformimidamide (0.2 g) as a gum. 1 H-NMR(400MHz,DMSO-d6)δ7.45(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,1H),2.91(s,3H),2.18(s,3H),2.05(s,3H),1.11(bs,3H) EXAMPLES

[0290] N'-(4-(3-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide Step A: Preparation of N-(4-(3-chlorobenzyl)-2,5-dimethylphenyl)acetamide To a suspension of N-(4-(3-chlorobenzoyl)-2,5-dimethylphenyl)acetamide (3.8 g, 12.59 mmol) in dichloromethane (40 ml) was added triethylsilane (8.05 g, 69.3 mmol) at 0° C. After stirring the reaction mixture for 10 minutes, boron trifluoride ethyl ether complex (8.04 g, 56.7 mmol) was added dropwise to the reaction mixture. After addition, the reaction mixture was stirred at room temperature for 36 hours. 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 phase was dried over anhydrous Na2SO4. The mixture was filtered and concentrated under reduced pressure. The residue was then purified by column chromatography on silica gel using hexane:ethyl acetate as eluent to give the desired N-(4-(3-chlorobenzyl)-2,5-dimethylphenyl)acetamide (2.5 g) as a solid. LCMS (M+H) 288.79

[0291] 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 ethanol (80 ml)-water (20 ml) was charged potassium hydroxide (26.9 g, 480 mmol) 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 phase was dried over anhydrous Na2SO4. The mixture was then filtered and evaporated under reduced pressure. The residue was then purified by column chromatography on silica gel using hexane:ethyl acetate as eluent to give the desired 4-(3-chlorobenzyl)-2,5-dimethylaniline (2.5 g) as a solid. LCMS (M+H) 246.75

[0292] Step C: Preparation of N'-(4-(3-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide A solution of 4-(3-chlorobenzyl)-2,5-dimethylaniline (0.8 g, 3.26 mmol) in trimethyl orthoformate (30.0 ml) containing 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 give an intermediate, which was then dissolved in 1,4-dioxane (30 ml). N-ethylmethylamine (2.83 ml, 32.6 mmol) was added and the reaction mixture was heated at 103° C. for 2 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give a residue, which was then purified by column chromatography on silica gel using hexane:ethyl acetate as eluent to give the desired N'-(4-(3-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide (0.3 g) as a gum. 1 H-NMR(400MHz,DMSO-d6)δ7.68-7.42(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) EXAMPLES

[0293] N'-(2,5-dimethyl-4-(4-(methylsulfonyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide Steps A and B were carried out as described in the above examples. Step C: Preparation of N'-(2,5-dimethyl-4-(4-(methylsulfonyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide To a solution of 2,5-dimethyl-4-(4-(methylsulfonyl)benzyl)aniline (0.3 g, 1.037 mmol) in trimethyl orthoformate (15 ml) was added p-toluenesulfonic acid monohydrate (0.020 g, 0.104 mmol) and heated at 100° C. for 4 hours. After completion of the reaction, the volatiles were evaporated. The residue was dissolved in 1,4-dioxane (15.00 ml) and N-ethylmethylamine (0.270 ml, 3.11 mmol) was added. The reaction mixture was heated at 100° C. for 4 hours and after completion of the reaction, dioxane was evaporated and the residue was purified by preparative HPLC to give N'-(2,5-dimethyl-4-(4-(methylsulfonyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide (240 mg) as a gum. 1H NMR(400MHz,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,3H),2.10(s,3H),2.08(s,3H),1.10(t,3H,);LCMS(M+H)359.15 EXAMPLES

[0294] N'-(2,5-dimethyl-4-(4-(methylsulfinyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide Steps A and B were carried out as described in the above examples. Step C: Preparation of N'-(2,5-dimethyl-4-(4-(methylsulfinyl)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), oxone (0.282 g, 0.919 mmol) was added and heated at 65° C. for 2 hours. After completion of the reaction, the reaction mixture was filtered and the filtrate was evaporated to give a residue, which was then purified by column to give N'-(2,5-dimethyl-4-(4-(methylsulfinyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide (0.25 g). 1H NMR(400MHz,DMSO-d6)δ7.57-7.55(m,3H),7.29(d,2H,),6.88(s,1H),6.55(s,1H),3.90(s,2H),3.3 5-3.29(m,2H),2.90(s,3H),2.68(s,3H),2.09(s,3H),2.08(s,3H),1.10(t,3H,);LCMS(M+H)343.20 EXAMPLES

[0295] N'-[4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl]-N-methylimidoformamide Steps A and B were carried out as described in the above examples. 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-dimethylaniline (1.5 g, 4.87 mmol) in trimethyl orthoformate (10 ml) was added p-toluenesulfonic acid monohydrate (0.926 g, 4.87 mmol) and stirred at 103° C. for 4 hours. The reaction mixture was then concentrated under reduced pressure to give the intermediate. To this intermediate was added 1,4-dioxane (10.00 ml) and methylamine (20.02 ml, 40.0 mmol). 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 give the crude product. The crude product was purified by flash chromatography using hexane:ethyl acetate to give the desired N'-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide (400 mg) as a gum. 1 H-NMR(400MHz,DMSO-d6)δ7.61(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) EXAMPLES

[0296] N'-[2-chloro-4-(3-fluorobenzyl)-5-methylphenyl]-N-methylimidoformamide Steps A and B were carried out as described in the above examples. 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), p-toluenesulfonic acid monohydrate (0.038 g, 0.200 mmol) was added and stirred at 103° C. for 4 hours. The reaction mixture was then concentrated under reduced pressure to give the intermediate. To this intermediate, 1,4-dioxane (10.00 ml) and methylamine (20.02 ml, 40.0 mmol) were added. 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 the crude product. The crude product was purified by flash chromatography using hexane:ethyl acetate to give the desired N'-(2-chloro-4-(3-fluorobenzyl)-5-methylphenyl)-N-methylformimidamide (600 mg) as a gum. 1 H-NMR(400MHz,DMSO-d6)δ7.60(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,3H),2.10(s,3H) EXAMPLES

[0297] 4-(3-chloro-4-fluorobenzyl)-2,5-dimethyl-N-[(Z)-morpholin-4-ylmethylidene]aniline Steps A and B were carried out as described in the above examples. 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), p-toluenesulfonic acid monohydrate (10.82 mg, 0.057 mmol) was added and stirred at 103° C. for 4 hours. The reaction mixture was concentrated under reduced pressure to give a residue, which was dissolved in 1,4-dioxane (10.00 ml). Morpholine (0.991 ml, 11.37 mmol) was added 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 residue. This was purified by column chromatography using hexane:ethyl acetate as eluent to give the desired N-(4-(3-chloro-4-fluorobenzyl)-2,5-dimethylphenyl)-1-morpholinomethanimine (270 mg) as a gum. 1 H-NMR(400MHz,DMSO-d6)δ7.61(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) EXAMPLES

[0298] 4-(3-chloro-4-fluorobenzyl)-2,5-dimethyl-N-[(Z)-piperidin-1-ylmethylidene]aniline Steps A and B were carried out as described in the above examples. 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-dimethylaniline (0.3 g, 1.137 mmol) in trimethyl orthoformate (10 ml), p-toluenesulfonic acid monohydrate (10.82 mg, 0.057 mmol) was added and stirred at 103° C. for 4 hours. The reaction mixture was concentrated under reduced pressure to give a residue. To the residue, 1,4-dioxane (10 ml) and piperidine (0.969 g, 11.37 mmol) were added 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 give the crude compound. The crude product was purified by flash chromatography using hexane:ethyl acetate to give the desired N-(4-(3-chloro-4-fluorobenzyl)-2,5-dimethylphenyl)-1-(piperidin-1-yl)methanimine (301 mg) as a gum. 1 H-NMR(400MHz,DMSO-d6)δ7.53(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) EXAMPLES

[0299] 4-(3-Bromo-2-fluorobenzyl)-2,5-dimethyl-N-[(Z)-morpholin-4-ylmethylidene]aniline Steps A and B were carried out as described in the above examples. 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-dimethylaniline (0.25 g, 0.811 mmol) in trimethyl orthoformate (10 ml) was added p-toluenesulfonic acid monohydrate (7.71 mg, 0.041 mmol) and stirred at 103° C. for 4 hours. The reaction mixture was then concentrated under reduced pressure to give the intermediate. To this intermediate was added 1,4-dioxane (10 ml) and morpholine (0.71 ml, 8.11 mmol) and heated to 103° C. for 2 hours. After completion of the reaction, the volatiles were evaporated under reduced pressure to give the crude product. The crude product was purified by flash chromatography using hexane:ethyl acetate to give the desired N-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-1-morpholinomethanimine (250 mg) as a gum. 1 H-NMR(400MHz,DMSO-d6)δ7.61(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) EXAMPLES

[0300] 4-(3-Bromo-2-fluorobenzyl)-2,5-dimethyl-N-[(Z)-piperidin-1-ylmethylidene]aniline Steps A and B were carried out as described in the above examples. 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-dimethylaniline (0.25 g, 0.811 mmol) in trimethyl orthoformate (10 ml), p-toluenesulfonic acid monohydrate (7.71 mg, 0.041 mmol) was added and stirred at 103° C. for 4 hours. The reaction mixture was concentrated under reduced pressure to give the intermediate. To the intermediate, 1,4-dioxane (10 ml) and piperidine (0.691 g, 8.11 mmol) were added 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 give the crude product. The crude product was purified by flash chromatography using hexane:ethyl acetate to give the desired N-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-1-(piperidin-1-yl)methanimine (280 mg) as a gum. 1 H-NMR(400MHz,DMSO-d6)δ7.54(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(4H),2.10(s,3H),2.07(s,3H),1.66-1.55(m,2H),1.55-1.41(m,4H) EXAMPLES

[0301] N-Ethyl-N'-[4-(4-fluorobenzyl)-2,5-dimethylphenyl]-N-methylimidoformamide Steps A and B were carried out as described in the above examples. Step C: Preparation of N-ethyl-N'-(4-(4-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide To a solution of 4-(4-fluorobenzyl)-2,5-dimethylaniline (0.3 g, 1.308 mmol) in trimethyl orthoformate (10 ml), p-toluenesulfonic acid monohydrate (0.012 g, 0.065 mmol) was added and stirred at 103° C. for 4 hours. The reaction mixture was then concentrated under reduced pressure to give the intermediate. To this intermediate, 1,4-dioxane (10 ml) and N-ethylmethylamine (1.137 ml, 13.08 mmol) were added 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 the crude product. The crude product was purified by flash chromatography using hexane:ethyl acetate to give the desired N-ethyl-N'-(4-(4-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide (0.3 g) as a gum. EXAMPLES

[0302] N-Ethyl-N'-[4-(3-methoxybenzyl)-2,5-dimethylphenyl]-N-methylimidoformamide Step A: Preparation of N'-(2,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-N-ethyl-N-methylformimidamide To a solution of N'-(4-bromo-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide (2.7 g, 10.03 mmol) in 1,4-dioxane (27 ml) was 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, then catalytic PdCl2(dppf)-CH2Cl2 adduct (0.819 g, 1.003 mmol) was added under nitrogen atmosphere and the reaction mixture was heated to 110° C. for 2 hours. The reaction mixture was then concentrated under reduced pressure to give the crude product. The crude product was purified by flash chromatography using hexanes:ethyl acetate to give the desired N'-(2,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-N-ethyl-N-methylformimidamide (2.5 g) as a gum. LCMS (M+H) 317.25

[0303] 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-dioxaborolan-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 1,4-dioxane (10 ml)-water (0.01 ml) was purged with nitrogen for 20 min. Pd(Ph3p)4 (0.164 g, 0.142 mmol) was added and the reaction mixture was heated to 110 °C for 2 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and the crude product was purified by preparative HPLC to give the desired N-ethyl-N'-(4-(3-methoxybenzyl)-2,5-dimethylphenyl)-N-methylformimidamide (0.3 g) as a gum. 1H-NMR(400MHz,DMSO-d6)δ7.59-7.44(bs,1H),7.12(d,2H),7.01(d,2H),6.83-6.78(s,1H),6.51(s,1 H),3.75(s,2H),3.42-3.30(bs,2H),2.87(s,3H),2.39(s,3H),2.06(s,3H),2.05(s,3H),1.07(t,,3H) EXAMPLES

[0304] N-Ethyl-N'-(4-(methoxy(phenyl)methyl)-2,5-dimethylphenyl)-N-methylformimidamide A solution of (4-amino-2,5-dimethylphenyl)(phenyl)methanol (0.7 g, 3.08 mmol) in trimethyl orthoformate (20 ml) containing p-toluenesulfonic acid monohydrate (0.029 g, 0.154 mmol) was stirred at 103° C. for 4 hours. The reaction mixture was then concentrated under reduced pressure to give the intermediate. This intermediate was charged with 1,4-dioxane (20 ml) and N-ethylmethylamine (2.68 ml, 30.8 mmol) 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 residue which was then purified by column chromatography on silica gel using hexane:ethyl acetate as eluent to give the desired N-ethyl-N'-(4-(methoxy(phenyl)methyl)-2,5-dimethylphenyl)-N-methylformimidamide (0.4 g) as a gum. 1 H-NMR(400MHz,DMSO-d6)δ7.60(bs,1H),7.36-7.18(m,5H),7.03(s,1H),6.52(s,1H),5.35(s,1H),3.4 8-3.34(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) EXAMPLES

[0305] N'-(2,5-dimethyl-4-(2-phenyl-1,3-dithiolan-2-yl)phenyl)-N-ethyl-N-methylformimidamide 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 CHCl (25 ml), ethane-1,2-dithiol (1.057 g, 11.22 mmol) was added, acetic acid (0.642 ml, 11.22 mmol) was cooled to 0° C., then boron trifluoride etherate (0.782 ml, 6.17 mmol) was added, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane, and then quenched by pouring the reaction mixture dropwise into aqueous NaOH, the mixture was separated, and the combined organic layers were dried over anhydrous NaSO and concentrated. The crude product was purified by column chromatography to give the desired N-(2,5-dimethyl-4-(2-phenyl-1,3-dithiolan-2-yl)phenyl)acetamide (1.8 g). LCMS (M+H) 344.50

[0306] 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 a solution of potassium hydroxide (8.98 g, 160 mmol) and the reaction mixture was heated at 90° C. for 15 hours. The reaction mixture was evaporated under reduced pressure. The residue was diluted with water (150 ml) and extracted with ethyl acetate (3×150 ml). The combined organic layers were dried over anhydrous sodium sulfate and concentrated. The crude compound was purified by column chromatography to give the desired product 2,5-dimethyl-4-(2-phenyl-1,3-dithiolan-2-yl)aniline (1.2 g). LCMS (M+H) 302

[0307] 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 mg, 0.896 mmol) in trimethyl orthoformate (25 ml) was added PTSA (10 mg) and the reaction mixture was heated at 103° C. for 4 h. The solvent was evaporated under reduced pressure. Dioxane (25.00 ml) was charged to the residue, then N-ethylmethylamine (0.779 ml, 8.96 mmol) was added to the reaction mixture and the reaction mixture was heated at 103° C. for 2 h. After complete conversion of the starting material, the reaction mixture was concentrated under reduced pressure and the crude compound was purified by preparative HPLC to give the desired N'-(2,5-dimethyl-4-(2-phenyl-1,3-dithiolan-2-yl)phenyl)-N-ethyl-N-methylformimidamide (220 mg). 1 H-NMR(400MHz,DMSO-d6)δ7.79(s,1H),7.64(s,1H),7.38(d,2H),7.23-7.27(m,2H),7.16-7.20(m,1 H),6.52(s,1H),3.51-3.40(3H),3.40-3.32(3H),2.91(s,3H),2.20(s,3H),1.74(s,3H),1.11(t,3H)

[0308] As described herein, the compounds of general formula (I) exhibit very high fungicidal activity against a number of plant pathogens that attack important agricultural crops. The activity of the compounds of the invention was evaluated against one or more of the following:

[0309] Biological Test Examples (In Vitro Tests) Example 1: Pyricularia oryzae (Rice Blast): Compounds were dissolved in 0.3% DMSO and then added to potato dextrose agar medium immediately prior to dispensing into Petri plates. 5 ml of medium containing compounds at the desired concentration was dispensed into 60 mm sterile Petri plates. After solidification, each plate was inoculated with a 5 mm sized mycelium disk taken from the outer edge of an actively growing virulent culture plate. Plates were incubated in a growth chamber at 25°C and 60% relative humidity for 7 days and the thickening growth was measured.In these tests, 300 ppm of compounds 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, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 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 3, 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, 1 20, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 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, 187, 188, 189, 190, 191, 192, 193, 194, 195, 196, 197, 198, 199, 198, 199, 199, 2, 183, 184, 185, 186, 188, 189, 190, 193, 194, 195, 196, 197, 198, 199, 200, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 232, 233, 234, 235, 2 16, 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 provided greater than 75% control compared to untreated controls which showed widespread disease incidence.

[0310] Example 2: Rhizoctonia solani (Rice sheath blight / Potato black spot): Compounds were dissolved in 0.3% DMSO and then added to potato dextrose agar medium immediately prior to dispensing into Petri plates. 5 ml of medium containing compounds at the desired concentration was dispensed into 60 mm sterile Petri plates. After solidification, each plate was inoculated with a 5 mm sized mycelium disk taken from the outer edge of an actively growing virulent culture plate. Plates were incubated in a growth chamber at 25°C temperature and 60% relative humidity for 7 days and the thickening growth was measured.In these tests, 300 ppm of compounds 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, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 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, 127, 128, 1, 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, 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, 189, 191, 193, 196, 197, 198, 199, 200, 201, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 2 14, 215, 216, 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 provided greater than 80% control compared to untreated controls which showed widespread disease incidence.

[0311] Example 3: Botrytis cinerea (gray mold): Compounds were dissolved in 0.3% DMSO and then added to potato dextrose agar medium immediately prior to dispensing into Petri plates. 5 ml of medium containing compounds at the desired concentration was dispensed into 60 mm sterile Petri plates. After solidification, each plate was inoculated with a 5 mm sized mycelium disk taken from the outer edge of an actively growing toxic culture plate. Plates were incubated in a growth chamber at 22°C temperature and 90% relative humidity for 7 days and the thickening growth was measured.In these tests, 300 ppm of compounds 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, 81, 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, 172, 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, 234, 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 yielded over 80% compared to untreated controls which showed widespread disease incidence.

[0312] Example 4: Alternaria solani (tomato / potato late blight): Compounds were dissolved in 0.3% DMSO and then added to potato dextrose agar medium immediately prior to dispensing into Petri plates. 5 ml of medium containing compounds at the desired concentration was dispensed into 60 mm sterile Petri plates. After solidification, each plate was inoculated with a 5 mm sized mycelium disk taken from the outer edge of an actively growing virulent culture plate. Plates were incubated in a growth chamber at 25°C temperature and 60% relative humidity for 7 days and thickening growth was measured.In these tests, compounds 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, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 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, 127, 12 4, 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, 127, 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, 176, 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, 2 20, 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, 272 and 273 provided greater than 75% control compared to untreated controls which showed widespread disease incidence.

[0313] Example 5: Colletotrichum capsici (Anthracnose): Compounds were dissolved in 0.3% DMSO and then added to potato dextrose agar medium immediately prior to dispensing into Petri plates. 5 ml of medium containing compounds at the desired concentration was dispensed into 60 mm sterile Petri plates. After solidification, each plate was inoculated with a 5 mm sized mycelium disk taken from the outer edge of an actively growing virulent culture plate. Plates were incubated in a growth chamber at 25°C and 60% relative humidity for 7 days and the thickening growth was measured. In these tests, 300 ppm of compounds 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, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 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, 127, 128, 129, 130, 131, 132, 133, 134, 135, , 76, 78, 79, 80, 81, 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, 116, 117, 118, 119, 120, 121, 122, 123, 124, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 1 37, 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, 174, 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 provided greater than 80% control compared to untreated controls which showed widespread disease incidence.

[0314] Example 6: Septoria lycopersici (tomato spot disease): Compounds were dissolved in 0.3% DMSO and then added to potato dextrose agar medium immediately prior to dispensing into Petri plates. 5 ml of medium containing compounds at the desired concentration was dispensed into 60 mm sterile Petri plates. After solidification, each plate was inoculated with a 5 mm sized mycelium disk taken from the outer edge of an actively growing virulent culture plate. Plates were incubated in a growth chamber at 25°C and 70% relative humidity for 7 days and the thickening growth was measured. In these tests, compounds 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, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 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, 127, 128, 129, 130, 13 3, 64, 66, 67, 68, 69, 70, 71, 72, 74, 81, 82, 83, 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, 2 15, 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 provided greater than 70% control compared to untreated controls which showed widespread disease incidence.

[0315] Example 7: Fusarium culmorum (corn bottom rot): Compounds were dissolved in 0.3% DMSO and then added to potato dextrose agar medium immediately prior to dispensing into Petri plates. 5 ml of medium containing compounds at the desired concentration was dispensed into 60 mm sterile Petri plates. After solidification, each plate was inoculated with a 5 mm sized mycelium disk taken from the outer edge of an actively growing virulent culture plate. Plates were incubated in a growth chamber at 25°C temperature and 60% relative humidity for 7 days and thickening growth was measured. In these tests, 300 ppm of compounds 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, 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, 176, 177, 178, 179, 180, 181, 182, 183, 184, 185, 186, 187, 188, 189, 190, 191, 192, 193, 194, 195, 196, 197, 198, 199, 198, 199, 200, 201, 202, 203, 204, 205, 20 5, 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, 20 9, 210, 211, 212, 213, 214, 215, 220, 221, 222, 223, 224, 225, 239, 249, 250, 252, 253, 256, 257, 258, 259, 260, 261, 262, 263, 269 and 271 provided 75% control compared to untreated controls which showed widespread disease incidence.

[0316] Biological test example (greenhouse) Example A: Pyricularia oryzae in rice Compounds were dissolved in 2% DMSO / acetone and then mixed with water to a calibrated spray volume of 50 ml. This 50 ml spray solution was poured into a spray bottle for further application.

[0317] To test the preventive activity of the compounds, healthy young rice seedlings / plants grown in a greenhouse were sprayed with a preparation of the active compound in a spray cabinet at the stated application rate using a hollow cone nozzle. One day after treatment, 1.4x10 6 The plants were inoculated with a spore suspension (sterile water) containing the Pyricularia oryzae inoculum of 1000 mg / kg / day. The inoculated plants were then kept in a greenhouse chamber at a temperature of 24°C and 95% relative humidity for disease manifestation.

[0318] Visual evaluation of compound performance was done by rating disease severity (on a scale of 0-100%) on treated plants 3, 7, 10 and 15 days after application. Compound efficacy (% control) was calculated by comparing disease ratings on treatments with untreated controls. Sprayed plants were also evaluated for phytotoxic effects of compounds by recording symptoms such as necrosis, chlorosis and growth stunting. In these tests, compounds 26, 44, 48, 51, 63, 87, 93, 94, 96, 103, 110, 112, 120, 133, 135, 148, 149 and 183 at 500 ppm provided 70-100% control compared to untreated controls which showed widespread disease development. None of these compounds showed any phytotoxicity to rice crops.

[0319] Example B: Testing for Fusarium culmorum in wheat Compounds were dissolved in 2% DMSO / acetone and then mixed with water to a calibrated spray volume of 50 ml. This 50 ml spray solution was poured into a spray bottle for further application.

[0320] To test the preventive activity of the compounds, healthy young wheat plants grown in a greenhouse were sprayed with a preparation of the active compound in a spray cabinet using a hollow cone nozzle at the stated application rate. One day after treatment, 2x10 6 The plants were inoculated with a spore suspension (2% malt) containing Fusarium culmorum inoculum of 1000 mg / kg. The inoculated plants were then maintained in a greenhouse chamber at a temperature of 24 °C and 80–90% relative humidity for disease manifestation.

[0321] Visual evaluation of compound performance was performed by rating disease severity (on a scale of 0-100%) on treated plants 3, 7, 10 and 15 days after application. Compound efficacy (% control) was calculated by comparing disease ratings on treatments to untreated controls. Sprayed plants were also evaluated for phytotoxic effects of compounds by recording symptoms such as necrosis, chlorosis and growth stunting. In these tests, compounds 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 provided 70-100% control compared to untreated controls which showed widespread disease development. None of these compounds showed any phytotoxicity to wheat crops.

[0322] Example C: Botrytis cinera test in tomatoes Compounds were dissolved in 2% DMSO / acetone and then mixed with water to a calibrated spray volume of 50 ml. This 50 ml spray solution was poured into a spray bottle for further application.

[0323] To test the preventive activity of the compounds, healthy young bean / chili plants grown in a greenhouse were sprayed with a preparation of the active compound in a spray cabinet using a hollow cone nozzle at the stated application rate. One day after treatment, 1.2x10 6The plants were inoculated with a spore suspension (2% malt) containing Botrytis cinerea inoculum of 1000 mg / kg / day. The inoculated plants were then kept in a greenhouse chamber at temperatures between 18 and 20 °C and 90–100% relative humidity for disease expression.

[0324] Visual evaluation of compound performance was performed on treated plants by rating disease severity (on a scale of 0-100%) at 3, 7, 10 and 15 days after application. Compound efficacy (% control) was calculated by comparing disease ratings in treated plants with untreated controls. Sprayed plants were also evaluated for phytotoxic effects of compounds by recording symptoms such as necrosis, chlorosis and stunting. In these tests, compounds 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, 101, 102, 103, 104, 105, 133, 166, 170, 179, 180, and 184 at 500 ppm provided 70-100% control compared to untreated controls which showed widespread disease incidence. None of these compounds showed any phytotoxicity to tomato crops.

[0325] Example D: Alternaria solani test on tomato Compounds were dissolved in 2% DMSO / acetone and then mixed with water to a calibrated spray volume of 50 ml. This 50 ml spray solution was poured into a spray bottle for further application.

[0326] To test the preventive activity of the compounds, healthy young tomato plants grown in a greenhouse were sprayed with a preparation of the active compound in a spray cabinet using a hollow cone nozzle at the stated application rate. One day after treatment, 0.24x10 6 The plants were inoculated with a spore suspension (2% malt) containing Alternaria solani inoculum of 1000 mg / kg. The inoculated plants were then maintained in a greenhouse chamber at temperatures of 22–24 °C and 90–95% relative humidity for disease expression.

[0327] Visual evaluation of compound performance was performed by rating disease severity (on a scale of 0-100%) on treated plants 3, 7, 10 and 15 days after application. Compound efficacy (% control) was calculated by comparing disease ratings on treatments to untreated controls. Sprayed plants were also evaluated for phytotoxic effects of compounds by recording symptoms such as necrosis, chlorosis and growth stunting. In these tests, compounds 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 provided 70-100% control compared to untreated controls which showed widespread disease development. None of these compounds showed any phytotoxicity towards tomato crops.

[0328] Table 3 below shows a comparative analysis of compounds reported in the prior art (WO200046184) and the compounds of the present invention.

[0329] [Table 30]

[0330] [Table 31]

[0331] From the above comparison and analysis, it can be concluded that the compounds of the present invention unexpectedly exhibit higher biological activity against the tested pathogens when compared to the biological activity of the comparative compounds.

[0332] While the invention has been described with reference to certain preferred embodiments, other embodiments will become apparent to those skilled in the art from consideration of this specification. It will be apparent to those skilled in the art that many modifications, both to materials and methods, can be made without departing from the scope of the invention.

Claims

1. 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-(methylsulfinyl)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-(methylsulfinyl)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-(4-(3-chloro-4-fluorobenzyl)-2,5-dimethylphenyl)-1-morpholinomethanimine; N-(4-(3-chloro-4-fluorobenzyl)-2,5-dimethylphenyl)-1-(piperidin-1-yl)methanimine; N-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-1-morpholinomethanimine; N-(4-(3-bromo-2-fluorobenzyl)-2,5-dimethylphenyl)-1-(piperidin-1-yl)methanimine; N-(2-chloro-4-(3-fluorobenzyl)-5-methylphenyl)-1-morpholinomethanimine; N-(2-chloro-4-(3-fluorobenzyl)-5-methylphenyl)-1-(piperidin-1-yl)methanimine; N-(2-chloro-4-(2-chlorobenzyl)-5-methylphenyl)-1-morpholinomethanimine; 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-(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)methanimine; N-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-1-(piperidin-1-yl)methanimine; N-(4-(4-fluorobenzyl)-2,5-dimethylphenyl)-1-(piperidin-1-yl)methanimine; N-(4-(2-chlorobenzyl)-2,5-dimethylphenyl)-1-morpholinomethanimine; 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-(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'-(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-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-(dimethylamino)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'-(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-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-(trifluoromethoxy)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-chloro-4-(2,6-difluorobenzyl)-5-methylphenyl)-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'-(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'-(5-chloro-4-(cyano(5-fluoro-2-methylphenyl)methyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide; N'-(4-(1-(4-bromophenyl)vinyl)-5-chloro-2-methylphenyl)-N-ethyl-N-methylformimidamide; 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-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 hydrochloride; N-ethyl-N-methyl-N'-(5-methyl-4-(3-methylbenzyl)-2-(methylsulfonyl)phenyl)formimidamide; N-ethyl-N'-(5-fluoro-2-methyl-4-(3-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide; and N'-(4-(cyano(3-(trifluoromethyl)phenyl)methyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide; and agriculturally acceptable salts, stereoisomers, diastereoisomers, enantiomers, tautomers, or N-oxides of said compounds.

2. 10. A composition for controlling or preventing plant pathogenic microorganisms, comprising a compound according to claim 1 and one or more inert carriers.

3. 3. The composition of claim 2, further comprising one or more active compounds selected from fungicides, insecticides, molluscicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and / or mixtures thereof.

4. The composition described in claim 2, wherein the concentration of the compound described in claim 1 is in the range of 1 to 90 weight % based on the total weight of the composition.

5. The composition described in claim 2, wherein the concentration of the compound described in claim 1 is in the range of 5 to 50 weight % based on the total weight of the composition.

6. 2. Use of the compounds according to claim 1 for controlling plant pathogens and bacteria in agricultural and / or horticultural crops.

7. 10. Use of the compounds according to claim 1 for controlling or preventing phytopathogenic fungi in agricultural and / or horticultural crops.

8. 3. Use of the composition according to claim 2 for controlling or preventing plant pathogens, bacteria in agricultural and / or horticultural crops.

9. 9. The use according to claim 8, wherein the agricultural crop is selected from the group consisting of cereals, maize, rice, soybean and other legumes, fruits and fruit trees, nuts and nut trees, citrus and citrus trees, any horticultural plants, cucurbits, oil plants, tobacco, coffee, tea, cocoa, sugar beet, sugar cane, cotton, potato, tomato, onion, pepper and other plants, and ornamental plants.

10. 2. A method for controlling or preventing the infestation of phytopathogenic fungi or bacteria in useful plants in agricultural and / or horticultural crops, in which a compound according to claim 1 is applied to the plant, to a part or to a site thereof.

11. 13. A method for controlling or preventing the infestation of phytopathogenic fungi or bacteria in useful plants in agricultural and / or horticultural crops, in which a compound according to claim 1 is applied to the seeds of the plants.

12. 13. A method of controlling or preventing plant pathogens or bacteria in agricultural and / or horticultural crops using a compound according to claim 1, which comprises applying an effective dose of the compound comprising an amount of compound in the range of 1 g to 5 kg per hectare of agricultural or horticultural crop.

13. 11. The method of claim 10, wherein the agricultural crop is selected from the group consisting of cereals, corn, rice, legumes, fruits and fruit trees, nuts and nut trees, citrus and citrus trees, horticultural plants, cucurbits, oil plants, tobacco, coffee, tea, cocoa, sugar beet, sugar cane, cotton, potato, tomato, onion, pepper and other plants, and ornamental plants.

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