JPWO2018069842A5 - - Google Patents

Description

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

Controlling crop damage caused by phytopathogenic microorganisms is crucial for achieving high crop efficiency. For example, damage from plant diseases to ornamental plants, vegetables, upland crops, grains and fruit crops can result in a significant reduction in productivity, thereby increasing costs for consumers. Many products are commercially available to control such damage. There is still a need for new compounds that are more effective, less costly, less toxic, more environmentally safe, and / or have different mechanisms of action. Certain phenylamine derivatives are disclosed in the literature as antibacterial active ingredients in pest control agents. For example, WO2000046184, WO2003093224, WO2003024219, WO20050895447, and WO2005120234 disclose the use of phenylamine derivatives, especially phenylamidine, as fungicides, alone or as part of a composition. WO2004005242 discloses certain phenylbenzamide compounds, methods of producing such compounds, and their use for controlling unwanted microorganisms.

US4173633 discloses a phenylurea compound and a composition as an insecticide containing this compound. JP08291146 discloses an N-substituted phenylsulfonamide compound having excellent herbicidal activity, particularly a herbicide for paddy fields. WO2008110314 discloses fluoroalkylphenylamidine as a fungal removal compound, a method for preparing the same, and a method for using such a compound to protect seeds from unwanted microorganisms. One other PCT application publication WO2011095462 discloses a phenylamine derivative containing carboxamide, a method for preparing it, and a pesticide, mite control, mollusk control or mollusk composition containing this derivative.

Although the effectiveness of the phenylamine derivative described in the prior art is good, it remains desired in various cases. Therefore, in agriculture, there is always great interest in using new pest control compounds to avoid and / or control the development of microorganisms such as fungi or bacterial pathogens or pests that are resistant to known active ingredients. I'm collecting. Therefore, new compounds with higher activity than those already known are used with the aim of reducing the amount of active compounds used while maintaining at least the same efficacy as those already known. Is of great interest.

Here, we have found a new family of compounds with the above-mentioned effects or advantages. Thus, a new family of compounds according to the invention, namely phenyl ring substituted 4-substituted phenylamine derivatives, allows for unexpected and much higher activity against unwanted microorganisms such as fungi or bacterial pathogens or pests. To.

The present invention has the general formula (I).

の４－置換フェニルアミン誘導体に関し、置換基の定義は、上記の詳細な説明において定義されている。

With respect to the 4-substituted phenylamine derivative of, the definition of substituent is defined in the above detailed description.

Therefore, the present invention has the general formula (I).

式中、
Ｒ^１は、水素、ＣＮ、ＳＲ’’、Ｓ（Ｏ）_ｎＲ’’、ＯＲ’’、Ｃ_１～１２－アルキル、Ｃ_１～１２－アルコキシ、Ｃ_{１～１２－}アルキルチオ、Ｃ_２～１２－アルケニル、Ｃ_２～１２－アルキニル、Ｃ_１～１２－ハロアルキル、Ｃ_２～１２－ハロアルケニル、Ｃ_２～１２－ハロアルキニル、Ｃ_３～８－シクロアルキル、Ｃ_４～８－シクロアルケニル、Ｃ_５～８－シクロアルキニルからなる群から選択され、環式環系において、１個または複数の炭素原子は、Ｎ、Ｏ、およびＳ（Ｏ）_ｎからなる群から選択されるヘテロ原子により置き換えられていてもよく；
Ｒ^２およびＲ^３は、独立して、水素、ＣＮ、Ｓ（Ｏ）_ｎＲ’’、ＯＲ’、（Ｃ＝Ｏ）－Ｒ’’、Ｃ_１～１２－アルキル、Ｃ_２～１２－アルケニル、Ｃ_２～１２－アルキニル、Ｃ_１～１２－ハロアルキル、Ｃ_２～１２－ハロアルケニル、Ｃ_２～１２－ハロアルキニル、Ｃ_３～８－シクロアルキル、Ｃ_４～８－シクロアルケニル、Ｃ_５～８－シクロアルキニル、Ｃ_５～１８－アリール、Ｃ_７～１９－アラルキル、Ｃ_７－１９－アルカリールからなる群から選択され；環式環系において、１個または複数の炭素原子は、Ｎ、Ｏ、およびＳ（Ｏ）_ｎからなる群から選択されるヘテロ原子により置き換えられていてもよく；
Ｒ^１およびＲ^２、Ｒ^２およびＲ^３またはＲ^１およびＲ^３は、それらが結合している原子と共に、またはＣ、Ｎ、Ｏ、Ｓからなる群から選択されるさらなる原子と共に、ならびにＣ（＝Ｏ）、Ｃ（＝Ｓ）、Ｓ（Ｏ）_ｍおよびＳｉＲ’_２からなる群から選択される１～３つの環員を任意選択で含めて、４～７員環を形成してもよく、この環は、一部が、１つまたは複数のＸ、Ｒ’、ＯＲ’、ＳＲ’、ＮＲ’_２、ＳｉＲ’_３、ＣＯＯＲ’、ＣＮ、およびＣＯＮＲ’_２により置換されていてもよく；Ｒ^１、Ｒ^２およびＲ^３の基は全て、Ｘ、Ｒ’、ＯＲ’、ＳＲ’、ＮＲ’_２、ＳｉＲ’_３、ＣＯＯＲ’、ＣＮ、およびＣＯＮＲ’_２からなる群から選択される１つまたは複数の基により任意選択で置換されていてもよく；
Ｒ^４、Ｒ^５、Ｒ^６およびＲ^７は、独立して、水素、Ｘ、ＣＮ、ＳＣＮ、ＳＦ_５、Ｓ（Ｏ）_ｎＲ’’、ＳｉＲ’_３、ＯＲ’’、ＮＲ’Ｒ’’、（Ｃ＝Ｏ）－Ｒ’’、ＣＲ’－ＮＲ’’、Ｃ_１～１２－アルキル、Ｃ_２～１２－アルケニル、Ｃ_２～１２－アルキニル、Ｃ_１～１２－ハロアルキル、Ｃ_２～１２－ハロアルケニル、Ｃ_２～１２－ハロアルキニル、Ｃ_１～１２－ハロアルコキシ、Ｃ_１～１２－ハロアルキルチオ、Ｃ_３～８－シクロアルキル、Ｃ_４～８－シクロアルケニル、Ｃ_５～８－シクロアルキニル、Ｃ_３～８－シクロアルキルオキシ、Ｃ_３～８－シクロアルキルチオ、Ｃ_５～１８－アリール、Ｃ_７～１９－アラルキル、Ｃ_７～１９－アルカリールからなる群から選択され；環式環系において、１個もしくは複数の炭素原子は、Ｎ、Ｏ、およびＳ（Ｏ）_ｎからなる群から選択されるヘテロ原子により置き換えられていてもよく；上述の基は全て、Ｘ、Ｒ’、ＯＲ’、ＳＲ’、ＮＲ’_２、ＳｉＲ’_３、ＣＯＯＲ’、ＣＮ、およびＣＯＮＲ’_２からなる群から選択される１つもしくは複数の基により任意選択で置換されていてもよく；または
Ｒ^４およびＲ^７もしくはＲ^５およびＲ^６は、それらが結合している原子と共に、もしくはＣ、Ｎ、Ｏ、Ｓからなる群から選択されるさらなる原子と共に、ならびにＣ（＝Ｏ）、Ｃ（＝Ｓ）、Ｓ（Ｏ）_ｍおよびＳｉＲ’_２からなる群から選択される１～３つの環員を任意選択で含めて、４～７員環を形成してもよく、この環は、一部が、１つもしくは複数のＸ、Ｒ’、ＯＲ’、ＳＲ’、ＮＲ’_２、ＳｉＲ’_３、ＣＯＯＲ’、ＣＮ、およびＣＯＮＲ’_２により置換されていてもよく；Ｒ^４、Ｒ^５、Ｒ^６およびＲ^７の基は全て、Ｘ、Ｒ’、ＯＲ’、ＳＲ’、ＮＲ’_２、ＳｉＲ’_３、ＣＯＯＲ’、ＣＮ、およびＣＯＮＲ’_２からなる群から選択される１つもしくは複数の基により任意選択で置換されていてもよく；
Ｒ^８は、水素、ＣＮ、ＳＣＮ、Ｓ（Ｏ）_ｎＲ’’、ＳｉＲ’_３、ＮＲ’Ｒ’’、（Ｃ＝Ｏ）－Ｒ’’、ＣＲ’＝ＮＲ’’、Ｃ_１～１２－アルキル、Ｃ_２～１２－アルケニル、Ｃ_２～１２－アルキニル、Ｃ_１～１２－ハロアルキル、Ｃ_２～１２－ハロアルケニル、Ｃ_２～１２－ハロアルキニル、Ｃ_３～８－シクロアルキル、Ｃ_４～８－シクロアルケニル、Ｃ_５～８－シクロアルキニル、Ｃ_５～１８－アリール、Ｃ_７～１９－アラルキル、Ｃ_７～１９－アルカリールからなる群から選択され；環式環系において、１個または複数の炭素原子は、Ｎ、Ｏ、およびＳ（Ｏ）_ｎからなる群から選択されるヘテロ原子により置き換えられていてもよく；上述の基は全て、Ｘ、Ｒ’、ＯＲ’、ＳＲ’、ＮＲ’_２、ＳｉＲ’_３、ＣＯＯＲ’、ＣＮ、およびＣＯＮＲ’_２からなる群から選択される１つまたは複数の基により置換されていてもよく；
Ａは、縮合または非縮合Ｃ_６～１８－アリール、Ｃ_５～１８－ヘテロアリールからなる群から選択され、１個または複数の炭素原子は、Ｎ、Ｏ、Ｓから選択されるヘテロ原子により置き換えられ、またＲ^９の１つまたは複数の基により任意選択で置換されたＣ（＝Ｏ）、Ｃ（＝Ｓ）、Ｓ（Ｏ）_ｍおよびＳｉＲ’_２からなる群から選択される１～３つの環員を任意選択で含み；
Ｒ^９は、水素、Ｘ、ＣＮ、ＳＣＮ、ＳＦ_５、Ｒ’’、ＯＲ’’、ＮＯ_２、ＮＲ’’_２、ＳｉＲ’_３、（Ｃ＝Ｏ）－Ｒ’’、Ｓ（Ｏ）_ｎＲ’’、ＯＳ（Ｏ）_ｎＲ’’、ＯＳｉＲ’_３、ＮＲ’Ｓ（Ｏ）_ｎＲ’’、Ｃ_１～８－アルキル－Ｓ（Ｏ）_ｎＲ’’、Ｃ_１～８－アルキル－（Ｃ＝Ｏ）－Ｒ’’、ＣＲ’＝ＮＲ’’、Ｓ（Ｏ）_ｎＣ_５～１８－アリール、Ｓ（Ｏ）_ｎＣ_７～１９－アラルキル、Ｓ（Ｏ）_ｎＣ_７～１９－アルカリール、Ｃ_１～１２－アルキル、Ｃ_２～１２－アルケニル、Ｃ_２～１２－アルキニル、Ｃ_１～１２－ハロアルキル、Ｃ_２～１２－ハロアルケニル、Ｃ_２～１２－ハロアルキニル、Ｃ_１～１２－アルコキシ、Ｃ_１～１２－アルキルチオ、Ｃ_１～１２－ハロアルコキシ、Ｃ_１～１２－ハロアルキルチオ、Ｃ_３～１２－シクロアルキル、Ｃ_４～８－シクロアルケニル、Ｃ_５～８－シクロアルキニル、Ｃ_３～８－シクロアルキルオキシ、Ｃ_３～８－シクロアルキルチオ、Ｃ_７～１９－アラルキル、Ｃ_７～１９－アルカリール；二環式Ｃ_５～１２－アルキル、Ｃ_７～１２－アルケニルからなる群から選択され；環式環系において、１個もしくは複数の炭素原子は、Ｎ、Ｏ、およびＳ（Ｏ）_ｎからなる群から選択されるヘテロ原子により置き換えられていてもよく；上述の基は全て、Ｘ、Ｒ’、ＯＲ’、ＳＲ’、ＮＲ’_２、ＳｉＲ’_３、ＣＯＯＲ’、ＣＮ、およびＣＯＮＲ’_２からなる群から選択される１つもしくは複数の基により置換されていてもよく；または、２つのＲ^９が、それらが結合している原子と共に、置換されていてもよい環を形成してもよく；
Ｒ^８、Ｒ^９およびＲ^１０の基は全て、Ｘ、Ｒ’、ＯＲ’、ＳＲ’、ＮＲ’_２、ＳｉＲ’_３、ＣＯＯＲ’、ＣＮ、およびＣＯＮＲ’_２からなる群から選択される１つまたは複数の基により任意選択で置換されていてもよく；
Ｘは、ハロゲンを表し；
Ｒ’は、水素、１つまたは複数のＸにより任意選択で置換された直鎖もしくは分岐鎖Ｃ_１～１２－アルキルまたは環式Ｃ_３～１０－アルキルを表し；
Ｒ’’は、水素；ＮＲ’_２、ＯＲ’、直鎖または分岐鎖Ｃ_１～１２－アルキル、Ｃ_１～１２－ハロアルキル、環式Ｃ_３～８－アルキルであって、Ｘ、Ｒ’、ＯＲ’、ＳＲ’、ＮＲ’_２、ＳｉＲ’_３、ＣＯＯＲ’、ＣＮ、およびＣＯＮＲ’_２からなる群から選択される１つまたは複数の基により任意選択で置換されたもの、１つまたは複数のＲ’により任意選択で置換されたＣ_５～１８－アリールを表し；
ｍおよびｎは整数を表し、ｎ＝０、１または２であり、ｍ＝１または２である）の化合物に関する。

During the ceremony
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 . -Alkoxy, C _2-12 -alkynyl, C _1-12 -haloalkyl, C _2-12 -haloalkoxy, C _2-12 -haloalkynyl, C _3-8 -cycloalkyl, C _4-8 -cycloalkenyl, C Selected from the group consisting of _5-8 -cycloalkoxynyl, in the cyclic ring system, one or more carbon atoms are replaced by heteroatoms selected from the group consisting of N, O, and S (O) _n . May be;
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, C _{5 ~} Selected from the group consisting of ₈ -cycloalkynyl, _C5-18 -aryl, _C7-19 -aralkyl, _C7-19 -alkalyl; in a cyclic ring system, one or more carbon atoms are N, It may be replaced by a heteroatom selected from the group consisting of O and S (O) _n ;
R ¹ and R ² , R ² and R ³ or R ¹ and R ³ with the atom to which they are attached, or with additional atoms selected from the group consisting of C, N, O, S, and C ( A 4- to 7-membered ring may be formed by optionally including 1 to 3 ring members selected from the group consisting of = O), C (= S), S (O) _m and _SiR'2 . , This ring may be partially substituted with one or _more X, R', OR', SR', NR' ₂ , _SiR'3 , COOR', CN, and CONR'2; The groups of R ¹ , R ² and R ³ are all _one selected from the group consisting of X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR'2. Or it may be optionally replaced by multiple groups;
R ⁴ , R ⁵ , R ⁶ and R ⁷ independently contain hydrogen, X, CN, SCN, SF ₅ , 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, C2-12-haloalkynyl, _{C1-12 -} haloalkoxy, C1-12 _- haloalkylthio, C3-8-cycloalkyl, _C4-8 -cycloalkenyl, _{C5-8 -} cyclo Selected from the group consisting of alkynyl, C _3-8 -cycloalkyloxy, C _3-8 -cycloalkylthio, C 5-18-aryl, C _7-19 -aralkyl, C _7-19 - _alkalyl ; cyclic ring. In the system, one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, and S (O) _n ; all of the above groups are X, R',. It may be optionally substituted with one or _more groups selected from the group consisting of OR', SR', _NR'2 , _SiR'3 , COOR', CN, and CONR'2; or ^R4 . And R ⁷ or R ⁵ and R ⁶ with the atoms to which they are bonded, or with additional atoms selected from the group consisting of C, N, O, S, and C (= O), C (= S). ), S (O) _m and 1 to 3 ring members selected from the group consisting of _SiR'2 may be optionally included to form a 4 to 7 member ring, the ring of which is partially. May be substituted with one or more X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR'₂; R ⁴ , R ⁵ , R ⁶ And all ^R7 groups are by one or _more groups selected from the group consisting of X, R', OR', SR', _NR'2 , _SiR'3 , COOR', CN, and CONR'2. It may be replaced by any option;
R ⁸ is hydrogen, CN, SCN, S (O) _n R'', _SiR'3 , NR'R'', (C = O) -R'', CR'= NR'', _C1-12 . -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 Selected from the group consisting of _-8 -cycloalkenyl, C5-8 _- cycloalkynyl, _C5-18 -aryl, _C7-19 -aralkyl, _C7-19 -alkalyl; one in a cyclic ring system. Alternatively, the plurality of carbon atoms may be replaced by a heteroatom selected from the group consisting of N, O, and S (O) _n ; all of the above groups are X, R', OR', SR'. , _NR'2 , _SiR'3 , COOR', CN, and CONNR'2 may be substituted with one or _more groups selected from the group;
A is selected from the group consisting of condensed or non-condensed C _6-18 -aryl, C _5-18 -heteroaryl, and one or more carbon atoms are replaced by heteroatoms selected from N, O, S. 1-3 selected from the group consisting of C ( ₌ O), C (= S), S (O) _m and ^SiR'2 optionally substituted by one or more groups of R9. Includes two members at will;
R ⁹ is hydrogen, X, CN, SCN, SF ₅ , R'', OR'', NO ₂ , NR'' ₂ , _SiR'3 , (C = O) -R'', S (O) _n . R'', OS (O) _n R'', _OSiR'3 , NR'S (O) _n R'', 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 -Alkoxy, S (O) _n C _{7- 19} -Alkoxy, C 1-12-Alkoxy, C 2-12-Alkoxy, C _2-12 -Alkinyl, C _{1-12 -} Haloalkyl, C _2-12 -Haloalkoxy, C _{2-12 -} Haloalkynyl, C _{1-12 -} alkoxy, C1-12 _- alkylthio, C1-12-haloalkoxy, _C1-12 -haloalkylthio, C3-12 _- cycloalkyl, _{C4-8 -} cycloalkenyl, C5-8- Cycloalkynyl, C _3-8 -cycloalkyloxy, C _3-8 -cycloalkylthio, C _7-19 -aralkyl, C _7-19 -alkoxy; bicyclic C _5-12 -alkyl, C _7-12- Selected from the group consisting of alkoxys; in the cyclic ring system, one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, and S (O) _n ; All of the above groups are replaced by one or _more groups selected from the group consisting of X, R', OR', SR', _NR'2 , _SiR'3 , COOR', CN, and CONR'2. Or the two ^R9s may form a ring, which may be substituted, with the atom to which they are attached;
The groups of R ⁸ , R ⁹ and R ¹⁰ are all _one selected from the group consisting of X, R', OR', SR', _NR'2 , _SiR'3 , COOR', CN, and CONR'2. Or it may be optionally replaced by multiple groups;
X represents halogen;
R'represents a linear or branched chain C _1-12 -alkyl or cyclic C _3-10 -alkyl optionally substituted with hydrogen, one or more Xs;
R'' is hydrogen; _NR'2 , OR', straight chain or branched chain C _1-12 -alkyl, C _1-12 -haloalkyl, cyclic C _3-8 -alkyl, X, R', One or more optionally substituted by one or _more groups selected from the group consisting of OR', SR', _NR'2 , _SiR'3 , COOR', CN, and CONR'2. Represents C _5-18 -aryl optionally substituted by R';
m and n represent integers, n = 0, 1 or 2, and m = 1 or 2).

According to one other embodiment, the compound of general formula (Ib) further comprises.

として説明され得、式中、
Ｒ^ｘおよびＲ^ｙは、独立して、水素、ヒドロキシ、ＣＮ、ＮＯ_２、ＣＯＯＲ’、Ｓ（Ｏ）_ｎＲ’’、ＯＲ’、（Ｃ＝Ｏ）－Ｒ’’、Ｃ_１～Ｃ_１２－アルキル、Ｃ_２～１２－アルケニル、Ｃ_２～１２－アルキニル、Ｃ_３～８－シクロアルキル、Ｃ_４～８－シクロアルケニル、Ｃ_５～８－シクロアルキニル、Ｃ_５～１８－アリール、Ｃ_７～１９－アラルキル、Ｃ_７～１９－アルカリールからなる群から選択され；環式環系において、１個もしくは複数の炭素原子は、Ｎ、Ｏ、およびＳ（Ｏ）_ｎからなる群から選択されるヘテロ原子により置き換えられていてもよく；または
Ｒ^ｘおよびＲ^ｙは、それらが結合している原子と共に、もしくはＣ、Ｎ、Ｏ、Ｓからなる群から選択されるさらなる原子と共に、ならびにＣ（＝Ｏ）、Ｃ（＝Ｓ）、Ｓ（Ｏ）_ｍおよびＳｉＲ’_２からなる群から選択される１～３つの環員を任意選択で含めて、３～７員環を形成してもよく、この環は、一部が、１つもしくは複数のＸ、Ｒ’、ＯＲ’、ＳＲ’、ＮＲ’_２、ＳｉＲ’_３、ＣＯＯＲ’、ＣＮ、およびＣＯＮＲ’_２により置換されていてもよく；
全ての他の置換基Ｒ^４～Ｒ^９は、第１の実施形態において定義された通りである。

Can be explained as, in the formula,
R ^x and R ^y are independently hydrogen, hydroxy, CN, NO ₂ , COOR', S (O) _n R'', OR', (C = O) -R'', C ₁ to 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 Selected from the group consisting of _{~ 19} -Aralkyl, C7-19-Alkaline; in the cyclic ring system, one or more carbon atoms are selected from the group consisting of N, O, and S (O) _n . It may be replaced by a heteroatom; or ^Rx and ^Ry with the atom to which they are attached, or with an additional atom selected from the group consisting of C, N, O, S, and C ( A 3- to 7-membered ring may be formed by optionally including 1 to 3 ring members selected from the group consisting of = O), C (= S), S (O) _m and _SiR'2 . , This ring may be partially substituted with one or _more X, R', OR', SR', NR' ₂ , _SiR'3 , COOR', CN, and CONR'2;
All other substituents ^R4 to ^R9 are as defined in the first embodiment.

In a preferred substitution of one other embodiment, R ¹ of the compound of general formula (I) is hydrogen, C _1-12 -alkyl, C _1-12 -alkoxy, C _1-12 -alkylthio, C _1-12 . -Haloalkyl, C _3-8 -Cycloalkyl.

In a more preferred substitution of one other embodiment, R ¹ of the compound of general formula (I) is hydrogen, C _1-6 -alkyl.

In a preferred substitution of one other embodiment, the compounds of general formula (I), R ² and R ³ , are C _1-12 -alkyl, C _2-6 -alkoxy, C _2-12 -alkynyl, C _{1-. 12} -alkoxy, C1-12 _- alkylthio, _{C1-12 -} haloalkyl, C3-8-cycloalkyl.

In one other embodiment, R ¹ and R ² , R ² and R ³ or R ¹ and R ³ are selected with the atoms to which they are attached or from the group consisting of C, N, O, S. With additional atoms, and optionally including 1 to 3 ring members selected from the group consisting of C (= O), C (= S), S (O) _m and SiR'2, ₄ to 7 A member ring may be formed, and the ring may be partially substituted with one or more X, R', OR', SR'and CN.

In one other embodiment, preferred ring-forming structures having substitutions R ¹ and R ² , R ² and R ³ or R ¹ and R ³ with the atoms to which they are attached are azetidine, pyrrolidine, imidazolidine, oxazolidine. , Piperidine, morpholine, thiomorpholine, piperazine, 1-methylpiperazine, 1-methylpyrrolidine, 1-methylpiperidine, 3-methyl-1,3-thiadinane.

In a preferred substitution of one other embodiment, the compounds of general formula ⁽ I), ^R4 and R5, are X, CN, S (O) _n R'', NR'R'', (C = O). -R'', CR'= NR'', C _1-12 -alkyl, C _2-6 -alkenyl, C _2-6 -alkynyl, C _1-12 -haloalkyl, C _1-12 -haloalkylthio, C _{3 ~ 8} -Cycloalkyl, C _3-8 -Cycloalkylthio.

In a preferred substitution of one other embodiment, the compounds of general formula (I), R ⁶ and R ⁷ , are hydrogen, X, CN, S (O) _n R'', NR'R'', (C = O) -R'', CR'= NR'', C1-12 _- alkyl, C2-6 _- alkenyl, C2-6-alkynyl, _{C1-12 -} haloalkyl, C1-12 _- haloalkylthio, C _3-8 -cycloalkyl and C _3-8 -cycloalkylthio.

In a preferred substitution of one other embodiment, R ⁸ on the compound of general formula (I) is hydrogen, CN, S (O) _n R'', NR'R'', (C = O) -R. '', CR'= NR'', C _1-12 -alkyl, C _2-6 -alkenyl, C _2-6 -alkynyl, C _1-12 -haloalkyl, C _3-8 -cycloalkyl, C _3-6 -Heterocyclyl, C _3-6 -Heterocyclyl alkyl.

In a preferred substitution of one other embodiment, R ⁹ on the compound of general formula (I) is X, CN, SCN, SF ₅ , R'', OR'', NO ₂ , NR'' ₂ , SiR. ' ₃ , (C = O) -R'', S (O) _n R'', OS (O) _n R'', _OSiR'3 , NR'S (O) _n R'', C _1-8 -Alkyl-S (O) _n R'', C _1-8 -alkyl- (C = O) -R'', CR'= NR'', SC _1-12 -alkyl, C _2-12 -alkenyl, C _2-12 -alkynyl, C _1-12 -haloalkyl, C _2-12 -haloalkenyl, C _1-12 -alkoxy, C _1-12 -alkylthio, C _1-12 -haloalkoxy, C _1-12 -halo Alkylthio, C _{3-12 -} cycloalkyl, _{C4-8 -} cycloalkenyl, C3-8-cycloalkyloxy, C3-8-cycloalkylthio.

^In one other embodiment, the two R9 substituents are with the atom to which they are attached, or with an additional atom selected from the group consisting of C, N, O, S, as well as C (= O). , C (= S), S (O) _m and SiR'2 may optionally include 1 to ₃ ring members selected from the group to form a 4 to 10 member ring. May be partially substituted with one or more X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR' ₂ .

In one other embodiment, preferred A is phenyl, naphthalenyl, frill, thienyl, pyrrolyl, thiazolyl, isooxazolyl, isothiazolyl, thiadiazolyl, pyrazolyl, oxazolyl, imidazolyl, oxadiazolyl, triazolyl substituted with one or more ^R9s . , Pyrizinyl, pyridadinyl, pyrimidinyl, pyrazinyl, triazinyl, indrill, benzoimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinazolinyl, cinnonyl.

In one other embodiment, A is phenyl, naphthalenyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, oxazolyl, isooxazolyl, oxadiazolyl, pyridinyl, pyridadinyl, pyrimidinyl, pyrazinyl, quinolinyl substituted with one or more ^R9s . be.

In one other embodiment, R ¹ to R ⁸ are selected from the group consisting of X, R'', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR' ₂ . It may be further optionally substituted with one or more groups.

In one other embodiment, the preferred compound of general formula (I) is
N'-(2,5-dimethyl-4- (phenylamino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (methyl (phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-5-methyl-4- (phenylamino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-5-methyl-4- (methyl (phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (N-phenylmethylsulfonamide) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (methyl (2-methyl-4- (perfluoropropane-2-yl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((4-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((3,4-dichlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-5-methyl-4- (methyl (3,4,5-trifluorophenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-5-methyl-4- (methyl (m-tolyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((3,4-dichlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((3-methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-5-methyl-4- (methyl (4- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-5-methyl-4- (methyl (p-tolyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((2-Methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-5-methyl-4- (N-phenylmethylsulfonamide) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((2-chlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((4-chlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((4-Methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((4-Methoxy-3-methylphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((3,4-dimethoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((3,5-dimethoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (methyl (m-tolyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N-ethyl-N'-(4-((3-methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
N'-(2,5-dimethyl-4- (methyl (p-tolyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N-Ethyl-N'-(4-((4-Methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
N-ethyl-N'-(4-((3-methoxyphenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
N'-(2,5-dimethyl-4- (m-tolylamino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (p-tolylamino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((4- (tert-butyl) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((4- (tert-butyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((2-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((2-chlorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N-Ethyl-N'-(4-((2-fluorophenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
N-Ethyl-N'-(4-((2-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
N'-(2-Chloro-4-((2-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N-Ethyl-N'-(4-((3-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
N-Ethyl-N'-(4-((4-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
N'-(4-((2-chlorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N-(4-(((Ethyl (methyl) amino) methylene) amino) -2,5-dimethylphenyl) -N-phenylacetamide;
N'-(2-chloro-5-methyl-4- (methyl (pyridine-2-yl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((4-chlorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N-Ethyl-N'-(4-((4-fluorophenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
N-ethyl-N'-(4-((2-methoxyphenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
N-Ethyl-N'-(4-((3-fluorophenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
N'-(2-Chloro-4-((2-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-4-((3-chlorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N- (3-chlorophenyl) -N, 2,5-trimethyl-4-((morpholinomethylene) amino) aniline;
N'-(2-Chloro-4-((3-chlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N- (3-chlorophenyl) -N, 2,5-trimethyl-4-((piperidine-1-ylmethylene) amino) aniline;
N-allyl-N'-(4-((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
N'-(4-((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-isopropyl-N-methylformimideamide;
N'-(4-((2-bromophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((3-chlorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N-Ethyl-N'-(4-((4-Methoxyphenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
N'-(2,5-dimethyl-4-((2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (methyl (2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4-((4- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4-((3- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (methyl (4- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (methyl (3- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4-((3- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((2-bromophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N-Ethyl-N'-(4-((2-Methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
N'-(2,5-dimethyl-4- (methyl (3- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-5-methyl-4-((3- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-5-methyl-4- (m-tolylamino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-4-((3-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-5-methyl-4- (o-tolylamino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((4-chlorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (o-tolylamino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((4-Methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-5-methyl-4- (methyl (o-tolyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((2-bromophenyl) amino) -2-chloro-5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((2-bromophenyl) (methyl) amino) -2-chloro-5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (methyl (o-tolyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((2-Methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-5-methyl-4-((2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-5-methyl-4- (methyl (2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-5-methyl-4-((4- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((3-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((4-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((3-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((4-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4-((3- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-5-methyl-4-((3- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-5-methyl-4- (methyl (3- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (methyl (3- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((2,6-difluorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((2,6-difluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((2,6-difluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((2,6-difluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((2-Chloro-6-fluorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((2-chloro-6-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((2-Chloro-6-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4-((4- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((2,6-dichloro-4- (trifluoromethyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4-((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-5-methyl-4-((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-5-methyl-4-((3- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4-((4- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-5-methyl-4-((4- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (methyl (2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-5-methyl-4- (methyl (2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (methyl (4- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-5-methyl-4- (methyl (4- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-5-methyl-4- (methyl (3- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-5-methyl-4- (N-phenylethylsulfonamide) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((2,4-dichloro-6- (trifluoromethyl) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-5-methyl-4-((4- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((2-Chloro-6-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (methyl (4- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-5-methyl-4- (methyl (4- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-5-methyl-4- (methyl (3- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4-((2-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-5-methyl-4-((2-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((3-((difluoromethyl) thio) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4-((4-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-5-methyl-4-((4-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (methyl (2-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-5-methyl-4- (methyl (2-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (methyl (4-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-5-methyl-4- (methyl (4-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((3-((difluoromethyl) thio) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4-((3-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4-((4- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-5-methyl-4-((4- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (methyl (3-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-5-methyl-4- (methyl (3-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (methyl (4- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-5-methyl-4- (methyl (4- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4-((3- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-5-methyl-4-((3- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (methyl (3- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-5-methyl-4- (methyl (3- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((3,5-bis (trifluoromethyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((3,5-bis (trifluoromethyl) phenyl) amino) -2-chloro-5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-5-methyl-4-((3-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((4- (dimethylamino) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((4- (dimethylamino) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((3-((difluoromethyl) thio) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((3-((difluoromethyl) thio) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((3- (difluoromethoxy) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((3- (difluoromethoxy) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((3- (difluoromethoxy) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4-((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4-((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4-((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((4- (difluoromethoxy) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((2,5-difluorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((2,5-difluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((3,5-bis (trifluoromethyl) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((3,5-bis (trifluoromethyl) phenyl) (methyl) amino) -2-chloro-5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4-((5-methyl-2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((2,5-difluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((2,5-difluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (methyl (5-methyl-2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((4-chloro-2- (trifluoromethyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((4-chloro-2- (trifluoromethyl) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((4-Chloro-2- (trifluoromethyl) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((4-chloro-2- (trifluoromethyl) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-5-methyl-4- (methyl (2- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((3- (difluoromethoxy) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-5-methyl-4-((2- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((2-Chloro-4- (trifluoromethyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((2-chloro-4- (trifluoromethyl) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((2-Chloro-4- (trifluoromethyl) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((2-Chloro-4- (trifluoromethyl) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4-((2- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N-Ethyl-N'-(4-((4-fluoro-3- (1,1,2,2-tetrafluoroethoxy) phenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide ;
N'-(2-Chloro-4-((4-fluoro-3- (1,1,2,2-tetrafluoroethoxy) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylform Imidamide;
5-Chloro-N- (2-fluorophenyl) -N, 2-dimethyl-4-((morpholinomethylene) amino) aniline;
N'-(2-chloro-4- (N- (2-fluorophenyl) methylsulfonamide) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N- (5-Chloro-4-(((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (2-fluorophenyl) acetamide;
N'-(2-Chloro-4-((2-fluorophenyl) (methyl) amino) -5-methylphenyl) -N, N-dimethylformimideamide;
N'-(2-Chloro-4- (ethyl (2-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
5-Chloro-N- (2-fluorophenyl) -N, 2-dimethyl-4-((morpholinomethylene) amino) aniline;
5-Chloro-N- (2-fluorophenyl) -N, 2-dimethyl-4-((thiomorpholinomethylene) amino) aniline;
N-ethyl-N'-(5-fluoro-4-((4-fluoro-3- (1,1,2,2-tetrafluoroethoxy) phenyl) amino) -2-methylphenyl) -N-methylform Imidamide;
N-Ethyl-N'-(5-Fluoro-4-((4-fluoro-3- (1,1,2,2-tetrafluoroethoxy) phenyl) (methyl) amino) -2-methylphenyl) -N -Methylformimide amide;
N- (5-Chloro-4-(((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (2-chlorophenyl) acetamide;
N'-(2-Chloro-4- (N- (2-chlorophenyl) methylsulfonamide) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((4-((difluoromethyl) thio) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((4-((difluoromethyl) thio) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((4-((difluoromethyl) thio) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((4-((difluoromethyl) thio) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4- (ethyl (phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N- (5-Chloro-4-(((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N-phenylacetamide;
N'-(2-Chloro-4-((2-((difluoromethyl) thio) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((2-((difluoromethyl) thio) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4- (ethyl (3-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((3- (difluoromethoxy) -4-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-4- (N- (3-methoxyphenyl) methylsulfonamide) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((3- (difluoromethoxy) -4-fluorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((3- (difluoromethoxy) -4-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((3- (difluoromethoxy) -4-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((2,5-dimethylphenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((2,5-dimethylphenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N- (5-Chloro-4-(((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (2-chlorophenyl) propionamide;
N-ethyl-N'-(5-fluoro-4-((4-methoxyphenyl) amino) -2-methylphenyl) -N-methylformimideamide;
N-Ethyl-N'-(5-Fluoro-4-((4-Methoxyphenyl) (Methyl) Amino) -2-Methylphenyl) -N-Methylformimideamide;
N- (5-Chloro-4-(((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (2-fluorophenyl) propionamide N'-(2-chloro-4-( N- (4-fluoro-3- (1,1,2,2-tetrafluoroethoxy) phenyl) methylsulfonamide) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4-((3- (1,1,2,2-tetrafluoroethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (methyl (3- (1,1,2,2-tetrafluoroethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N-Ethyl-N'-(4-((2-fluoro-5-methylphenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
N-ethyl-N'-(5-fluoro-4-((2-fluorophenyl) amino) -2-methylphenyl) -N-methylformimideamide;
N-Ethyl-N'-(4-((2-fluoro-5-methylphenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
N'-(2-Chloro-4-((2-fluoro-5-methylphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N-ethyl-N'-(5-fluoro-2-methyl-4- (phenylamino) phenyl) -N-methylformimideamide;
N'-(4-((2-chlorophenyl) amino) -5-fluoro-2-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((4- (tert-butyl) phenyl) amino) -5-fluoro-2-methylphenyl) -N-ethyl-N-methylformimideamide;
N-Ethyl-N'-(5-fluoro-2-methyl-4- (m-tolylamino) phenyl) -N-methylformimideamide;
N- (5-Chloro-4-(((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N-phenylpropionamide;
N- (5-Chloro-4-(((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (3-methoxyphenyl) acetamide N'-(2-chloro-4-((() 4-Fluoro-3-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N-Ethyl-N'-(4-((4-fluoro-3-methoxyphenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
N-Ethyl-N'-(4-((4-fluoro-3-methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
N'-(4-((2-((difluoromethyl) thio) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(4-((2-((difluoromethyl) thio) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-4-((4-fluoro-3-methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
N'-(2-bromo-6-fluoro-3-methyl-4- (phenylamino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-Chloro-5-methyl-4-((5-oxo-5,6,7,8-tetrahydronaphthalene-2-yl) amino) phenyl) -N-ethyl-N-methylformimideamide ;
N'-(2-bromo-6-fluoro-3-methyl-4- (methyl (phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2-chloro-5-methyl-4-((1-methylindolin-5-yl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4-((5-oxo-5,6,7,8-tetrahydronaphthalene-2-yl) amino) phenyl) -N-ethyl-N-methylformimideamide;
N-ethyl-N'-(5-fluoro-2-methyl-4- (methyl (phenyl) amino) phenyl) -N-methylformimideamide;
N'-(4-((4- (tert-butyl) phenyl) (methyl) amino) -5-fluoro-2-methylphenyl) -N-ethyl-N-methylformimideamide;
N-Ethyl-N'-(5-fluoro-2-methyl-4- (methyl (m-tolyl) amino) phenyl) -N-methylformimideamide;
N-ethyl-N'-(7-((2-methoxyphenyl) amino) -2,3-dihydro-1H-inden-4-yl) -N-methylformimideamide;
N-ethyl-N-methyl-N'-(7- (p-tolylamino) -2,3-dihydro-1H-inden-4-yl) formimideamide;
N'-(7-((4-chlorophenyl) amino) -2,3-dihydro-1H-indene-4-yl) -N-ethyl-N-methylformimideamide;
N-ethyl-N-methyl-N'-(4- (phenylamino) naphthalene-1-yl) formimideamide;
N'-(2,5-dimethyl-4- (pyridin-2-ylamino) phenyl) -N-ethyl-N-methylformimideamide;
N'-(2,5-dimethyl-4- (methyl (pyridine-2-yl) amino) phenyl) -N-ethyl-N-methylformimideamide and N'-(2-chloro-5-methyl-4) -(Ppyridine-2-ylamino) phenyl) -N-ethyl-N-methylformimideamide;
Is.
* Compound names were generated using Chemdraw Professional 16.0.

Any compound according to the invention may be present in one or more optical, geometric or chiral isomer forms, depending on the number of asymmetric centers in the compound. Accordingly, the present invention relates to all optical isomers and their racemic or scalemic mixtures (the term "scalemic" refers to mixtures of enantiomers in different proportions), as well as all possible stereoisomers in all proportions. Equally related to the mixture. Diastereoisomers and / or optical isomers can be separated according to methods known to those of skill in the art.

Also, any compound according to the invention may be present in one or more geometric isomer forms, depending on the number of double bonds in the compound. Therefore, the present invention is equally relevant to all geometric isomers and all possible mixtures in all proportions. Geometric isomers can be separated according to common methods known to those of skill in the art.

Also, any compound according to the invention may be present in one or more amorphous or homomorphic or polymorphic forms, depending on its preparation, purification, storage and various other influencing factors. Accordingly, the present invention relates to all possible amorphous, isomorphic and polymorphic forms in all proportions. Amorphous, isomorphic and polymorphic forms can be prepared and / or separated and / or purified according to common methods known to those of skill in the art.

In the above description, the term "alkyl", used alone or in compound terms such as "alkylthio" or "haloalkyl", refers to linear or branched alkyls such as methyl, ethyl, n-propyl, iso-propyl, Or it contains various butyl, pentyl or hexyl isomers.

"Alkenes" include linear or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, as well as various butenyl, pentenyl and hexenyl isomers. "Alkenyl" also includes polyenes such as 1,2-propazienyl and 2,4-hexadienyl.

"Alkynyl" includes linear or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and various butynyl, pentynyl and hexynyl isomers. The "alkynyl" may also include a moiety containing multiple triple bonds, such as 2,5-hexadynyl.

"Cycloalkyl" or "cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Cycloalkenyl includes, for example, cyclopropenium, cyclobutenyl, cyclopentenyl, and cyclohexenyl. Cycloalkynyl also refers to cyclic pentynyl, hexynyl, heptynyl and octynyl.

"Cycloalkyloxy" includes, for example, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy.

"Cycloalkylthio" includes, for example, cyclopropylthio, cyclobutylthio, cyclopentylthio.

The term "aryl", as used herein, is a group comprising any carbon-based aromatic group, including but not limited to phenyl, naphthalene, biphenyl, anthracene and the like. Aryl groups may be substituted or unsubstituted. Further, the aryl group may have a monocyclic structure, a fused ring structure, or may contain a plurality of ring structures bonded via one or a plurality of cross-linking groups such as a carbon-carbon bond.

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

The term "alkaline" refers to an aryl group having an alkyl group; as used herein, the term "alkali" includes both substituted and unsubstituted groups. An example of an alkaline reel group is a 4-methylphenyl group.

"Alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and various butoxy, pentoxy and hexyloxy isomers.

"Alkylthio" includes branched or linear alkylthio moieties such as methylthio, ethylthio and various propylthio, butylthio, pentylthio and hexylthio isomers.

The term "hetero" associated with a ring refers to a ring in which at least one ring atom is not carbon and may contain 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur. However, each ring contains 4 or less nitrogen, 2 or less oxygen and 2 or less sulfur.

The term "heterocycle" means a cyclic ring system in which at least one ring atom can contain a heteroatom independently selected from the group containing nitrogen, oxygen, sulfur, phosphorus, boron, etc., rather than carbon. do.

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

The term "non-aromatic heterocycle" refers to a fused or uncondensed 3-15 member, preferably 3-12 member saturated or fully or partially unsaturated heterocycle, monocyclic or polycyclic (spiro, condensed, crosslinked,). Non-condensed) Heterocycles, the heteroatoms are selected from the group of oxygen, nitrogen and sulfur; if the rings contain more than one oxygen atom, they are not directly adjacent; without limitation of non-aromatic heterocycles. Examples are oxetanyl, oxylanyl; aziridinyl; tiyranyl, azetidinyl, thietanyl, dithietanyl, diazetidinyl, 2-tetrahydrofuranyl; 3-tetrahydrofuranyl; 2-tetrahydrothienyl; 3-tetrahydrothienyl; 2-pyrrolidinyl; 3-pyrrolidinyl; 3-iso. Includes oxazolidinyl; 4-isooxazolidinyl; 5-isooxazolidinyl; 3-isothiazolidinyl; 4-isothiazolidinyl; 2-tetrahydropyranyl; 4-tetrahydropyranyl. This definition also applies to heterocyclyls as part of complex substituents such as heterocyclylalkyls (heterocyclic groups containing the alkyl moieties defined above), unless specifically defined elsewhere.

The term "heteroarylaryl" as used herein is fused or non-condensed 3-15 member, preferably 3-12 member, more preferably 5 or 6 member monocyclic or polycyclic unsaturated. It is a ring-containing group and contains a heteroatom selected from the group of oxygen, nitrogen, sulfur, phosphorus, boron and the like.

Unlimited examples of 5-membered heteroaryl groups are 2-furyl; 3-furyl; 2-thienyl; 3-thienyl; 2-pyrrolyl; 3-pyrrolyl; 3-isoxazolyl; 4-isoxazolyl; 5-isoxazolyl; 3-isothiazolyl. 4-Isotiazolyl; 5-Isotiazolyl; 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-oxadiazole-3-yl; 1,2,4-oxadiazole-5-yl; 1,2,4-thiadiazole-3-yl; 1,2,4-thiazole -5-yl; 1,2,4-triazole-3-yl; 1,3,4-oxadiazole-2-yl; 1,3,4-thiadiazole-2-yl and 1,3,4-triazole -2-Il; 1-Pyrrolyl; 1-Pyrazolyl; 1,2,4-Triazole-1-yl; 1-imidazolyl; 1,2,3-Triazole-1-yl; 1,3,4-Triazole-1 -Including ill etc.

Unlimited examples of 6-membered heteroaryl groups are 2-pyridinyl; 3-pyridinyl; 4-pyridinyl; 3-pyridazinyl; 4-pyridazinyl; 2-pyrimidinyl; 4-pyrimidinyl; 5-pyrimidinyl; 2-pyrazinyl; 1,3. , 5-Triazine-2-yl; 1,2,4-triazine-3-yl; 1,2,4,5-tetrazine-3-yl and the like.

Unlimited examples of benzofuran 5-member heteroaryls are indole-1-yl; indole-2-yl; indole-3-yl; indole-4-yl; indole-5-yl; indole-6-yl; indole- 7-il; benzimidazol-1-yl; benzimidazol-2-yl; benzimidazol-4-yl; benzimidazol-5-yl; indazole-1-yl; indazole-3-yl; indazole-4-yl; Indazole-5-yl; Indazole-6-yl; Indazole-7-il; Indazole-2-yl; 1-benzofuran-2-yl; 1-benzofuran-3-yl; 1-benzofuran-4-yl; 1- Benzofuran-5-yl; 1-benzofuran-6-yl; 1-benzofuran-7-yl; 1-benzothiophen-2-yl; 1-benzothiophen-3-yl; 1-benzothiophen-4-yl; 1 -Benzofuran-5-yl; 1-benzothiophen-6-yl; 1-benzothiophen-7-yl; 1,3-benzothiazole-2-yl; 1,3-benzothiazole-4-yl; 1, 3-benzothiazole-5-yl; 1,3-benzothiazole-6-yl; 1,3-benzothiazole-7-yl; 1,3-benzoxazole-2-yl; 1,3-benzoxazole-4 -Il; 1,3-benzoxazole-5-yl; 1,3-benzoxazole-6-yl; 1,3-benzoxazole-7-yl and the like are included.

Non-limiting examples of benzofused 6-membered heteroaryls are quinoline-2-yl; quinoline-3-yl; quinoline-4-yl; quinoline-5-yl; quinoline-6-yl; quinoline-7-yl; quinoline-. 8-yl; isoquinoline-1-yl; isoquinoline-3-yl; isoquinoline-4-yl; isoquinoline-5-yl; isoquinoline-6-yl; isoquinoline-7-yl; isoquinoline-8-yl and the like.

The term "halogen" is a single term or a compound term such as "haloalkyl" and includes fluorine, chlorine, bromine or iodine. Further, when used in a compound term such as "haloalkyl", the alkyl may be partially or completely substituted with halogen atoms which may be the same or different. Non-limiting examples of "haloalkyl" include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2 -Dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1,1-dichloro-2,2,2-trifluoroethyl, and 1,1,1-trifluoropropa-2- Including Il.

The terms "haloalkenyl", "haloalkynyl", "haloalkoxy" and "haloalkylthio" are similarly defined, provided that instead of the alkyl group, the alkenyl, alkynyl, alkoxy and alkylthio groups are one of the substituents. It exists as a department.

The total number of carbon atoms in the substituent is indicated by the prefix "C _i-j ", where i and j are numbers 1-21. For example, C _1-3 alkoxy refers from methoxy to propoxy. In the above enumeration, if the compound of formula (I) comprises one or more heterocyclic rings, all substituents are via the carbon or nitrogen by replacement of hydrogen on the available carbon or nitrogen. Is attached to these rings.

If the compound is substituted with said substituent having a subscript indicating the number of substituents which may be greater than 1, the substituent (if greater than 1) is independently defined as a substituent. Selected from the group of. Further, if the subscript indicates a range, for example (R) _i-j , the number of substituents can be selected from integers i-j (including them).

If the group contains a substituent that may be hydrogen, eg R ¹ or R ² , then when this substituent is considered hydrogen, it is understood to be equivalent to the unsubstituted group.

The present invention further relates to a composition for controlling unwanted microorganisms, comprising at least one compound of formula (I) and one or more inert carriers. The inert carrier further comprises an agriculturally suitable adjunct, solvent, diluent, surfactant and / or bulking agent and the like.

The invention further relates to at least one of the compounds of formula (I) and / or fungicides, fungicides, tick repellents, pesticides, nematicides, herbicides, bios. It relates to a composition for controlling undesired microorganisms, which comprises one or more activity compatible compounds selected from pesticides, plant growth regulators, antibiotics, fertilizers and / or mixtures thereof.

In the present invention, the concentration of the compound having the general formula (I) is further in the range of 1 to 90% by weight, preferably 5 to 50% by weight, based on the total weight of the composition. With respect to a composition.

The present invention also relates to methods for controlling unwanted microorganisms, wherein the compound of formula (I) is applied to the microorganism and / or its habitat.

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

The compounds of formula (I) may have strong antibacterial activity and in the protection of crops or horticultural crops, and the protection of such materials, unwanted microorganisms such as fungi, insects, mites, nematodes and bacteria. Can be used for control of.

The compound of formula (I) can have very good fungal removal properties and control, for example, Plasmodiohora, Egg fungi, Chytrids, Zygomycota, Ascomycetes, Basidiomycetes and Imperfecti in crop protection. Can be used for.

The compounds of formula (I) can be used as nematicides in crop protection, for example in the control of rhabditidae, fake nematodes, and Tripronchida.

The compound of formula (I) is used as an insecticide in crop protection, for example, for the control of Lepidoptera, Coleoptera, Hemiptera, Diptera, Orthoptera, Diptera, Orthoptera and E.optera. obtain.

The compound of formula (I) can be used as a tick repellent in crop protection, eg, for the control of Eriophyoidea, Eriophyoidea, Eupodoidea, and Tarsonemidae.

The compound of formula (I) can be used as a bactericidal agent in crop protection, for example in the control of Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corinebacterium and Streptomyces.

The compound of formula (I) can be used as a herbicide and can be effective against a wide range of economically important harmful monocotyledonous and dicotyledonous plants. The broad-leaved weed species of monocotyledonous plants include Phalaris, Ryegrass, Alopecurus, Phalaris, Barnyardgrasses, Fingergrasses, Setaria and Cynodon, and the perennial species Cynodon and Cynodon. Species, Imperata and Morokosi, as well as perennial Phalaris species can be included. The broad-leaved weed species of dicotyledonous plants include Galium, Sumire, Kuwagatasou, Dead-nettle, Hakobe, Convolanth, Shirogarashi, Ipomoea, Shida, Shikaregiku and Ichibi, as well as perennial broad-leaved. In the case of strain weeds, bindweed, Ipomoea, Ipomoea and Galium can be included. Harmful plants that occur in rice, such as the genus Echinochloa, the genus Alisma, the genus Alisma, the genus Eleocharis, the genus Scirpus, and the genus Kayatsurigusa, can be controlled by the compound of the formula (I).

The compounds of formula (I) can be used for curative or protective control of phytopathogenic fungi. Accordingly, the invention is also for controlling phytopathogenic fungi by using the active ingredient or composition of the invention applied to seeds, plants or plant parts, fruits, or soils in which plants grow. Regarding curative and protective methods.

The compound of formula (I) can be used to control or prevent phytopathogenic fungi, bacteria, insects, nematodes, mites in crops and / or garden crops.

The compound of formula (I) can be used for crop protection and the crops are grains, corn, rice, soybeans and other legumes, fruits and fruit trees, fruit and fruit trees, citrus and citrus fruit trees, any garden plants. , Uridae, oily plants, tobacco, coffee, tea, cacao, sugar cane, sugar cane, cotton, potatoes, tomatoes, onions, peppers and other plants, as well as ornamental plants.

According to the invention, as defined above, the carrier is a natural or synthetic organic or inorganic mixture or combination of active ingredients for better applicability, especially application to plants or plant parts or seeds. It is a substance. Carriers, which may be solid or liquid, are generally inert and should be suitable for agricultural use.

Useful solid carriers include, for example, ammonium salts and natural rock powders such as kaolin, clay, talc, cretaceous, quartz, attapargite, montmorillonite or diatomaceous soil, and synthetic rock powders such as pulverized silica, alumina and silicate; in granules. Useful solid carriers include, for example, ground and fragmented natural rocks such as pulverized stones, marbles, pebbles, sea foam and dolomites, as well as synthetic granules of inorganic and organic powders, as well as organic materials such as paper, shavings, coconut shells. , Corn panicles and tobacco stalk granules; useful emulsifiers and / or effervescent agents include, for example, nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers such as alkylaryls. Includes polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and even protein hydrolysates; suitable dispersants are nonionic and / or ionic substances such as alcohol-POE and / or -POP ethers, acids. And / or POP POE esters, alkylaryls and / or POP POE ethers, fats and / or POP POE adducts, POE-and / or POP-polyol derivatives, POE-and / or POP-sorbitan or-sugar adducts, alkyl Alternatively, it is from a class of aryl sulphates, alkyl-or aryl sulfonates and alkyl or aryl phosphates, or corresponding PO-ether adducts. Further suitable are oligomers or polymers obtained from, for example, vinyl monomers, acrylic acids, EO and / or PO alone, or in combination with, for example, (poly) alcohols or (poly) amines. It is also possible to use lignin and its sulfonic acid derivatives, unmodified and modified celluloses, aromatic and / or aliphatic sulfonic acids, as well as adducts thereof with formaldehyde.

The active ingredient may be applied as is, or converted to a special formulation, or its formulation or use form prepared from it, eg, ready-to-use solutions, emulsions, aqueous or oily suspensions. Turbids, powders, wettable powders, pastes, soluble powders, soluble tablets, powders, soluble granules, granules for spraying, Saspo emulsion concentrates, natural products impregnated with active ingredients, synthetic substances impregnated with active ingredients, It may be in the form of microencapsulation in a fertilizer or even a polymer substance. The application is customary and is achieved, for example, by watering, spraying, atomizing, nursery boxes, spraying, powdering, foaming, spreading and the like. It is also possible to distribute the active ingredient by the ultra-trace method, or to inject the active ingredient preparation / active ingredient itself into the soil. It is also possible to process plant seeds.

The active ingredient can be further converted to nanoformulations for the purpose of further improving water solubility, thermal stability, bioavailability, sensory properties, and physiological performance.

In addition, the choice of formulation type depends on the particular application.

The formulations referred to are in a manner known per se, eg, the active ingredient in at least one conventional bulking agent, solvent or diluent, emulsifier, dispersant and / or binder or fixing agent, wetting agent. Water repellents, desiccants and UV stabilizers where appropriate, and dyes and pigments, defoamers, preservatives, auxiliary thickeners, adhesives, gibererins and even other processing aids where appropriate. Can be prepared by mixing with.

The present invention includes not only formulations that are already readily available and can be distributed to plants or seeds by suitable equipment, but also commercial concentrates that need to be diluted with water prior to use.

The auxiliaries used have specific properties, such as certain technical and / or specific biological properties, in the composition itself and / or in the preparations obtained from it (eg spray liquids, seed powder coats). It may be a suitable substance to impart. Typical auxiliaries include bulking agents, solvents and carriers.

Suitable bulking agents are, for example, water, polar and non-polar organic chemical liquids, such as aromatic and non-aromatic hydrocarbons (eg, paraffin, alkylbenzene, alkylnaphthalene, chlorobenzene), alcohols and polyols (optionally substituted, ethers). Chemistry and / or esterified), ketones (eg acetone, cyclohexanones), esters (including fats and oils), and (poly) ethers, unsubstituted and substituted amines, amides, lactams (eg N-alkyl). Pyrrolidone) and lactones, sulfones, and sulfoxides (eg, dimethylsulfoxides).

It is understood that the liquefied gaseous bulking agent or carrier means a liquid that is gaseous under standard temperature and pressure, eg aerosol propellant, eg halohydrocarbons, or other butane, propane, nitrogen and carbon dioxide. To.

In formulations, natural and synthetic polymers in the form of tackifiers such as carboxymethyl cellulose, powder, granules or latex, such as Arabic gum, polyvinyl alcohol and polyvinyl acetate, or other natural phospholipids such as cephalin and lecithin, and synthetic. It is possible to use phospholipids. Additional additives may be minerals, vegetable oils and methylated seed oils.

When the bulking agent used is water, it is also possible to use an organic solvent as an auxiliary solvent, for example. Useful liquid solvents are essentially aromatics such as xylene, toluene or alkylnaphthalene, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or Paraffins such as petroleum distillates, alcohols such as butanol or glycol 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 other water. ..

The composition comprising the compound of formula (I) may further comprise an additional component, such as a surfactant. Suitable surfactants are emulsifiers and / or foaming agents, dispersants or wetting agents with ionic or nonionic properties, or mixtures of these surfactants. Examples are polyacrylic acid salts, lignosulfonic acid salts, phenol sulfonic acid or naphthalene sulfonic acid salts, polycondensates of ethylene oxide with fatty alcohols or fatty acids or fatty amines, substituted phenols (preferably alkylphenols or arylphenols). ), Sulfonic acid ester salts, taurine derivatives (preferably alkyl taurates), polyethoxylated alcohols or phenolic acid esters, polyol fatty esters, and derivatives of compounds including sulfates, sulfonates and phosphates, such as alkylarylpoly. Glycol ethers, alkyl sulphonates, alkyl sulphates, aryl sulphonates, protein hydrolysates, lignosulfite effluents, and methylcellulose. The presence of a surfactant is required if one of the active ingredients and / or one of the inert carriers is insoluble in water, and if the application is carried out with water. The proportion of surfactant is 5-40 weight percent of the composition of the invention.

Inorganic pigments such as dyes such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes and metallic phthalocyanine dyes, and trace amounts of salts such as iron, manganese, boron, copper, cobalt, molybdenum and zinc. It is possible to use nutrients.

Additional additives may be flavors, minerals or vegetables, optionally modified oils, waxes and nutrients (including micronutrients), such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salts. ..

Additional ingredients may be stabilizers such as cryostats, preservatives, antioxidants, photostabilizers, or other agents that improve chemical and / or physical stability.

Where appropriate, other additional components such as protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrants, stabilizers, sequestering agents, complexing agents may be present. In general, the active ingredient can be combined with any solid or liquid additive commonly used for formulation purposes.

The formulations are generally 0.05-99% by weight, 0.01-98% by weight, preferably 0.1-95% by weight, more preferably 0.5-90% by weight, most preferably 10-70% by weight. Includes% active ingredient.

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

The compounds and salts of formula (I), N-oxides, metal complexes, stereoisomers or polymorphs according to the invention can be used as is or in formulations thereof, eg, to extend the range of activity or tolerate. Can be mixed with known mixing partners to prevent the development of. Useful mixing partners include, for example, known fungicides, pesticides, acaricides, nematicides, biopesticides and fungicides. Mixtures with other known active ingredients such as herbicides, or fertilizers and growth regulators, toxicity mitigators and / or semiochemicals are also possible.

Examples of such chemical components are shown herein, but not exclusively. Some of them are described herein, for example, in The Pesticide Manual 17th Ed. Known and described in, or specified by their common names that can be searched on the Internet (eg, at www.alanwood.net/pesticides). Others are described by their system names according to the IUPAC nomenclature.

All named mixtures of classes (A)-(O) described below may optionally form salts with the appropriate base or acid, if the functional group allows. In some cases, it may appear as a stereoisomer or as a polymorph, even if not specifically mentioned. It is understood that they are also included herein. Examples of these are:

A) Inhibitors of ergosterol biosynthesis, such as (A01) aldimorph, (A02) azaconazole, (A03) bitertanol, (A04) bromconazole, (A05) cyproconazole, (A06) diclobutrazole, (A07). ) Diphenoconazole, (A08) Diniconazole, (A09) Diniconazole-M, (A10) Dodemorph, (A11) Dodemorph acetate, (A12) Epoxyconazole, (A13) Etaconazole, (A14) Phenalimol, (A15) Fembco Nazole, (A16) fenhexamide, (A17) fenpropidine, (A18) fenpropimorph, (A19) fluconazole, (A20) fluconazole, (A21) flusilazole, (A22) flutriazole, (A20) A23) Fluconazole, (A24) Fluconazole-cis, (A25) Hexaconazole, (A26) Imazalil, (A27) Imazalyl sulfate, (A28) Imibenconazole, (A29) Ipconazole, (A30) Metoconazole, (A31) Microbutanil , (A32) Naftifin, (A33) Nuarimol, (A34) Oxpoconazole, (A35) Paclobutrazole, (A36) Pefrazoate, (A37) Penconazole, (A38) Piperline, (A39) Prochloraz, (A40) Pro Piconazole, (A41) Prothioconazole, (A42) Pyributycarb, (A43) Pyriphenox, (A44) Kinconazole, (A45) Simeconazole, (A46) Spiroxamine, (A47) Tebuconazole, (A48) Terbinazole, (A49) ) Tetraconazole, (A50) triazimephon, (A51) triazimenol, (A52) tridemorph, (A53) triflumazole, (A54) trifolin, (A55) triticonazole, (A56) uniconazole, (A56) A57) Uniconazole-p, (A58) Biniconazole, (A59) Voliconazole, (A60) 1- (4-Chlorophenyl) -2- (1H-1,2,4-Triazole-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-d Chill-N-methylimideformamide, (A63) N-ethyl-N-methyl-N'-{2-methyl-5- (trifluoromethyl) -4- [3- (trimethylsilyl) propoxy] phenyl} imideformamide, (A64) O- [1- (4-methoxyphenoxy) -3,3-dimethylbutane-2-yl] -1H-imidazole-1-carbothioate, (A65) pyriisoxazole, (A66) 2-{ [3- (2-Chlorophenyl) -2- (2,4-difluorophenyl) oxylan-2-yl] methyl} -2,4-dihydro-3H-1,2,4-triazole-3-thione, (A67) ) 1-{[3- (2-Chlorophenyl) -2- (2,4-difluorophenyl) oxylan-2-yl] methyl} -1H-1,2,4-triazole-5-ylthiocyanate, (A68) 5- (Allylsulfanyl) -1-{[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxylan-2-yl] methyl} -1H-1,2,4-triazole, (A69) ) 2- [1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptane-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3- Thion, (A70) 2-{[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxylan-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) oxylan-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) oxylan-2-yl] methyl} -1H-1,2,4-triazole-5-ylthiocyanate, (A73) 1-{[rel (2R, 3R) -3- (2-chlorophenyl) )-2- (2,4-difluorophenyl) oxylan-2-yl] methyl} -1H-1,2,4-triazole-5-ylthiocyanate, (A74) 5- (allyl sulfanyl) -1-{[ rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxylan-2-yl] methyl} -1H-1,2,4-triazole, (A75) 5- (allyl sulfanyl) -1-{[rel (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxylan-2-yl] methyl} -1H- 1,2,4-Triazole, (A76) 2-[(2S, 4S, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl]- 2,4-Dihydro-3H-1,2,4-triazole-3-thione, (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, (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-trimethylheptane-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-Thion, (A84) 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2,4-triazole-1-yl) propan-2-ol , (A85) 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2) , 4-Triazole-1-yl) butane-2-ol, (A86) 2- [4- (4-chlorophenoxy) -2- (trifluoromethyl) phenyl] -1- (1H-1,2,4) -Triazole-1-yl) pentan-2-ol, (A87) 2- [2-chloro-4- (4-chlorophenoxy) phenyl] -1- (1H-1,2,4-triazole-1-yl) ) Butan-2-ol, (A88) 2- [2-chloro-4- (2,4-dichlorophenoxy) phenyl] -1- (1H-1,2,4-triazole-1-yl) propane2- All, (A89) (2R) -2- (1-chlorocyclopropyl) -4-[(1R) -2,2-dichlorocyclopropyl] -1- (1H-1,2,4-triazole-1-) Il) Butan-2-ol, (A90) (2R) -2- (1-chlorocyclopropyl) -4-[(1S) -2,2-dichlorocyclopropyl] -1- (1H-1,2, 4-Triazole-1-yl) butane-2-ol, (A91) (2S) -2- (1-chlorocyclopropyl) -4-[(1S) -2,2-dichlorocyclopropyl] -1-( 1H-1,2,4-triazole-1-yl) butane-2-ol, (A92) (2S) -2- (1-chlorocyclopropyl) -4-[(1R) -2,2-dichlorocyclo Propyl] -1- (1H-1,2,4-triazole-1-yl) butane-2-ol, (A93) (1S, 2R, 5R) -5- (4-chlorobenzyl) -2- (chloro Methyl) -2-methyl-1- (1H-1,2,4-triazole-1-ylmethyl) cyclopentanol, (A94) (1R, 2S, 5S) -5- (4-chlorobenzyl) -2- (Chloromethyl) -2-methyl-1- (1H-1,2,4-triazole-1-ylmethyl) cyclopentanol, (A95) 5- (4-chlorobenzyl) -2- (chloromethyl) -2 -Methyl-1- (1H-1,2,4-triazole-1-ylmethyl) cyclopentanol.

B) Inhibitors of the respiratory chain at complex I or II, such as (B01) bixaphen, (B02) boscalid, (B03) carboxamide, (B04) cipropamide, (B05) diflumethrim, (B06) fenfurum, (B07). Fluopyram, (B08) flutranil, (B09) fluxapyrazoled, (B10) flametopil, (B11) flumecyclox, (B12) isopyrazole (syn-epimalasemata 1RS, 4SR, 9RS and anti-epimarasemiform 1RS, 4SR, 9SR mixture), (B13) isopyrazam (anti-epimer semiform 1RS, 4SR, 9SR), (B14) isopyrazam (anti-epimer mirror image isomers 1R, 4S, 9S), (B15) isopyrazam (anti-epimer mirror image isomer) 1S, 4R, 9R), (B16) Isopyrazam (syn-epimer semiform 1RS, 4SR, 9RS), (B17) Isopyrazam (syn-epimer mirror image isomers 1R, 4S, 9R), (B18) Isopyrazam (syn-epimer mirror image) Isolates 1S, 4R, 9S), (B19) mepronil, (B20) oxycarboxamide, (B21) penflufen, (B22) penthiopyrazole, (B23) pidiflumethofen, (B24) sedaxane, (B25) thyfluzamide, (B24) B26) 1-methyl-N- [2- (1,1,2,2-tetrafluoroethoxy) phenyl] -3- (trifluoromethyl) -1H-pyrazole-4-carboxamide, (B27) 3- (difluoro) Methyl) -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] -1-methyl-1H-pyrazole-4-carboxamide, (B29) N- [1- (2,4-) Dichlorophenyl) -1-methoxypropan2-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (B30) 5,8-difluoro-N- [2- (2-fluoro-) 4-{[4- (Trifluoromethyl) pyridine-2-yl] oxy} phenyl) ethyl] quinazoline-4-amine, (B31) benzobindiflupyr, (B32) N-[(1S, 4R) -9 -(Dichloromethylene) -1,2,3,4-tetrahydro-1,4-metha Nonaphthalene-5-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (B33) N-[(1R, 4S) -9- (dichloromethylene) -1,2, 3,4-Tetrahydro-1,4-methanonaphthalene-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, (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-4-carboxamide, (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-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (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) benodanyl, (B44) 2-chloro-N -(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) pyridin-3-carboxamide, (B45) isofetamide, (B46) 1-methyl-3- (trifluoro) Methyl) -N- [2'-(trifluoromethyl) biphenyl-2-yl] -1H-pyrazole-4-carboxamide, (B47) N- (4'-chlorobiphenyl-2-yl) -3- (difluoro) Methyl) -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'-(propa-1-in-1-yl) biphenyl-2-yl] -1H-pyrazole-4-carboxamide, (B52) 5-fluoro-1,3-dimethyl-N- [4'-( Propa-1-in-1-yl) biphenyl-2-yl] -1H-pyrazole-4-carboxamide, (B53) 2-chloro-N- [4'-(propa-1-in-1-yl) biphenyl -2-yl] Nicotinamide, (B54) 3- (difluoromethyl) -N- [4'-(3,3-dimethylbuta-1-in-1-yl) biphenyl-2-yl] -1-methyl -1H-pyrazole-4-carboxamide, (B55) N- [4'-(3,3-dimethylbuta-1-in-1-yl) biphenyl-2-yl] -5-fluoro-1,3-dimethyl -1H-pyrazole-4-carboxamide, (B56) 3- (difluoromethyl) -N- (4'-ethynylbiphenyl-2-yl) -1-methyl-1H-pyrazole-4-carboxamide, (B57) N- (4'-Etinylbiphenyl-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-dimethylbuta-1-in-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-methylbuta-1-in-1-yl) biphenyl-2-yl] -1,3-dimethyl-1H-pyrazole-4-carboxamide, (B62) 2-chloro -N- [4'-(3-Hydroxy-3-methylbuta-1-in-1-yl) biphenyl-2-yl] nicotine amide, (B63) 3- (difluoromethyl) -N- [4'-( 3-Methyl-3-methylbuta-1-in-1-yl) biphenyl-2-yl] -1-methyl-1H-pyrazole-4-carboxamide, (B64) 5-fluoro-N- [4'-(3'-(3) -Methyl-3-methylbuta-1-in-1-yl) biphenyl-2-yl] -1,3-dimethyl-1H-pyrazole-4-carboxamide, (B65) 2-chloro-N- [4'-( 3-Methyl-3-methylbuta-1-in-1-yl) biphenyl-2-yl] nicotine amide, (B66) 1,3-dimethyl-N- (1,1,3-trimethyl-2,3-dihydro) -1H-inden-4-yl) -1H-pyrazol-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 -Il] -1H-pyrazole-4-carboxamide, (B69) 3- (difluoromethyl) -N-methoxy-1-methyl-N- [1- (2,4,6-trichlorophenyl) propan-2-yl ] -1H-pyrazole-4-carboxamide, (B70) 3- (difluoromethyl) -N- (7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)- 1-Methyl-1H-pyrazole-4-carboxamide, (B71) 3- (difluoromethyl) -N-[(3,R) -7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H -Inden-4-yl] -1-methyl-1H-pyrazole-4-carboxamide, (B72) 3- (difluoromethyl) -N-[(3S) -7-fluoro-1,1,3-trimethyl-2 , 3-Dihydro-1H-Inden-4-yl] -1-Methyl-1H-Pyrazole-4-Carboxamide.

C) Inhibitors of the respiratory chain in Complex III, such as (C01) amethoctrazine, (C02) amysulbrom, (C03) azoxystrobin, (C04) siazofamide, (C05) kumethoxystrobin, (C06) spumoxy. Strobin, (C07) dymoxystrobin, (C08) enoxastrobin, (C09) famoxadon, (C10) fenamiden, (C11) phenaminestrobin, (C12) fluphenoxystrobin, (C13) fluoxa Strobin, (C14) cresoxime-methyl, (C15) metminostrobin, (C16) mandestrobin, (C17) orisastrobin, (C18) picoxystrobin, (C19) pyracrostrobin, (C20) pyrametostrobin , (C21) pyraoxystrobin, (C22) pyribencarb, (C23) triclopyricalve, (C24) trifloxystrobin, (C25) (2E) -2- (2-{[6- (3-chloro-) 2-Methylphenoxy) -5-fluoropyrimidine-4-yl] oxy} phenyl) -2- (methoxyimino) -N-methylacetamide, (C26) (2E) -2- (methoxyimino) -N-methyl- 2-(2-{[({(1E) -1- [3- (trifluoromethyl) phenyl] etylidene} 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) etylidene] amino} oxy) methyl] phenyl} -2- (methoxyimino) -N-Methylacetamide, (C29) phenaminostrobin, (C30) 5-methoxy-2-methyl-4- (2-{[({(1E) -1- [3- (trifluoromethyl) phenyl]] Ethiliden} amino) oxy] methyl} phenyl) -2,4-dihydro-3H-1,2,4-triazol-3-one, (C31) methyl (2E) -2-{2-[({cyclopropyl [ (4-Methylphenyl) imino] methyl} sulfanyl) methyl] phenyl} -3-methoxyacrylate, (C32) N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formamide -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-dimethylpenta-3-enamide.

D) Inhibitors of mitosis and cell division, such as (D01) benomyl, (D02) carbendazim, (D03) chlorphenazole, (D04) dietofencarb, (D05) etaboxam, (D06) fluoride, (D07) alben. Dazole, (D08) pencyclon, (D09) thiobendazole, (D10) thiophanate-methyl, (D11) thiophanate, (D12) zoxamide, (D13) 5-chloro-7- (4-methylpyridazine-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.

E) Compounds capable of having multipoint action, such as (E01) Bordeaux solution, (E02) captahole, (E03) captan, (E04) chlorotalonyl, (E05) copper hydroxide, (E06) copper naphthenate, (E06) copper naphthenate. E07) Copper Oxide, (E08) Copper Oxychloride, (E09) Copper Sulfate (2+), (E10) Diclofluanide, (E11) Dithianone, (E12) Dodine, (E13) Dodine Free Base, (E14) Felbam, (E15) Fluoroholpet, (E16) Holpet, (E17) Guazatin, (E18) Guazatin Acetate, (E19) Imminoctazine, (E20) Imminoctazine Alvesilate, (E21) Imminoctadine Triacetate, (E22) Mancopper, Sulfur preparation containing (E23) mancozeb, (E24) maneb, (E25) methylam, (E26) methylam zinc, (E27) oxine-copper, (E28) propamidin, (E29) propineb, (E30) sulfur and calcium polysulfide. Things, (E31) copper, (E32) trillfluanide, (E33) xenib, (E34) diram, (E35) anilazine.

F) Compounds capable of inducing host defense, such as (F01) acibenzolar-S-methyl, (F02) isothianyl, (F03) probenazole, (F04) thiazinyl, (F05) laminarin.

G) Inhibitors of amino acid and / or protein biosynthesis, such as (G01) andprim, (G02) Blasticidin-S, (G03) cyprodinyl, (G04) kasugamycin, (G05) kasugamycin hydrochloride hydrate, (G06). ) Mepanipyrim, (G07) pyrimethanyl, (G08) 3- (5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinoline-1-yl) quinoline, (G09) oxytetracycline, (G10) )streptomycin.

H) Inhibitors of ATP production, such as (H01) fentin acetate, (H02) fentin chloride, (H03) fentin hydroxydo, (H04) silthiofam.

I) Inhibitors of cell wall synthesis, such as (I01) Bench Avaricarb, (I02) Dimethmorph, (I03) Fulmorph, (I04) Iprovaricarb, (I05) Mandipropamide, (I06) Polyoxin, (I07) Polyoxolim, (I08). Validamycin A, (I09) varifenalate, (I10) polyoxin B, (I11) (2E) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1-( Morpholine-4-yl) propa-2-ene-1-one, (I12) (2Z) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1-( Morpholine-4-yl) Propa-2-en-1-on.

J) Inhibitors of lipid and membrane synthesis, such as (J01) biphenyl, (J02) chloroneb, (J03) dichloran, (J04) edifenphos, (J05) etridiazole, (J06) iodocarb, (J07) iprobenphos, (J08). ) Isoprothiolan, (J09) propamocarb, (J10) propamocarb hydrochloride, (J11) prothiocarb, (J12) pyrazophos, (J13) quintozen, (J14) technazen, (J15) tocrophos-methyl.

K) Inhibitors of melanin biosynthesis, such as (K01) carpropamide, (K02) diclosimet, (K03) phenoxanyl, (K04) phthalide, (K05) pyrokyron, (K06) tolprocarb, (K07) tricyclazole.

L) Inhibitors of nucleic acid synthesis, such as (L01) Benalaxil, (L02) Benalaxil-M (Kiraluxil), (L03) Bupirimate, (L04) Closilacon, (L05) Dimethyrimol, (L06) Etilimol, (L07) Flaluxil, (L03) L08) Himexazole, (L09) Metalaxil, (L10) Metalaxyl-M (Mephenoxam), (L11) Offrace, (L12) Oxolinic acid, (L13) Oxolinic acid, (L14) Octinone.

M) Signal transduction inhibitors such as (M01) clozoline, (M02) phenpicronyl, (M03) fludioxonyl, (M04) iprodion, (M05) procymidone, (M06) quinoxyphene, (M07) binclozoline, (M08) proquinazide.

N) Compounds that can act as uncouplers, such as (N01) binapacryl, (N02) dinocup, (N03) ferlimzone, (N04) fluazinum, (N05) meptylzinocup.

O) Additional compounds such as (O01) benzazole, (O02) betoxazine, (O03) capsimicin, (O04) carboxylic, (O05) quinomethiocyanate, (O06) pyriophenone (clazaphenone), (O07) cufraneb, (O08) siflufenamide, (O09) Simoxanyl, (O10) Cyprosulfamide, (O11) Dazomet, (O12) Devacarb, (O13) Dichlorophene, (O14) Diclobenazox, (O15) Dichromedin, (O16) Diphenzocoat, (O17) Diphenzocoat methylsulfate, (O18) diphenylamine, (O19) ecomate, (O20) fenpyrazamine, (O21) fenhexamine, (O22) flumethobel, (O23) fluoroimide, (O24) flusulfamide, (O25) fluthianyl, (O24) O26) Fosetyl-Aluminum, (O27) Fosetyl-Calcium, (O28) Fosetyl-Sodium, (O29) Hexachlorobenzene, (O30) Irumamycin, (O31) Isothianyl, (O32) Metasulfocarb, (O33) Methylisothiocyanate , (O34) Metraphenone, (O35) Mildomycin, (O36) Natamycin, (O37) Nickeldimethyldithiocarbamate, (O38) Nitrotal-isopropyl, (O39) Oxamocarb, (O40) Oxyfenthine, (O41) Pentachlorophenol. And salts, (O42) phenotrin, (O43) picalbutrazox (O44) phosphate and its salts, (O45) propamocarb-phocetylate, (O46) propanosine-sodium, (O47) pyrimorph, (O48) pyraziflumid, (O49). ) Pyrol nitrin, (O50) tebuflokin, (O51) tecrophthalam, (O52) tornifanide, (O53) triazoxide, (O54) tricramide, (O55) zaryramid, (O56) (3S, 6S, 7R, 8R) -8- Benzyl-3-[({3-[(isobutyryloxy) methoxy] -4-methoxypyridine-2-yl} carbonyl) amino] -6-methyl-4,9-dioxo-1,5-dioxonan-7 -Il 2-methylpropionate, (O57) 1-(4- {4-[(5R) -5- (2,6-difluorophenyl) -4,5-dihydro-1,2-oxazole-3- Il] -1,3-thiazole-2-yl} pipe Lysine-1-yl) -2- [5-methyl-3- (trifluoromethyl) -1H-pyrazole-1-yl] etanone, (O58) 1- (4- {4-[(5S) -5-yl] (2,6-difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazole-2-yl} piperidin-1-yl) -2- [5-methyl- 3- (Trifluoromethyl) -1H-pyrazole-1-yl] etanone, (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) -on, (O63) 2,6-dimethyl-1H, 5H- [1,4] ditiino [2,3-c: 5,6-c'] dipyrazole-1,3,5,7 (2H, 6H) -Tetron, (O64) 2- [5-Methyl-3- (trifluoromethyl) -1H-pyrazole-1-yl] -1- (4- {4-[(5R) -5-yl] Phenyl-4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazole-2-yl} piperidin-1-yl) etanone, (O65) 2- [5-methyl-3-( Trifluoromethyl) -1H-pyrazole-1-yl] -1- (4- {4-[(5S) -5-phenyl-4,5-dihydro-1,2-oxazol-3-yl] -1, 3-Thiazole-2-yl} piperidin-1-yl) etanone, (O66) 2- [5-methyl-3- (trifluoromethyl) -1H-pyrazole-] -yl] -1- {4- [4 -(5-Phenyl-4,5-dihydro-1,2-oxazol-3-yl) -1,3-thiazole-2-yl] piperidin-1-yl} etanone, (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-imidazole) -5-Il] Pyridine, (O69) 2-phenylphenol and salt, (O70) 3- (4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline , (O71) 3,4,5-trichloropyridin-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-thiasiazol-2-thiol, (O76) 5 -Chloro-N'-phenyl-N'-(propa-2-in-1-yl) thiophen-2-sulfonohydrazide, (O77) 5-fluoro-2-[(4-fluorobenzyl) oxy] pyrimidin- 4-amine, (O78) 5-fluoro-2-[(4-methylbenzyl) oxy] pyrimidin-4-amine, (O79) 5-methyl-6-octyl [1,2,4] triazolo [1,5] -A] Pyrimidine-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-methylimideformamide, (O82) N- (4-chlorobenzyl) -3- [3- [3- Methoxy-4- (propa-2-in-1-yloxy) phenyl] propanamide, (O83) N-[(4-chlorophenyl) (cyano) methyl] -3- [3-methoxy-4- (propa-2) -In-1-yloxy) phenyl] propanamide, (O84) N-[(5-bromo-3-chloropyridine-2-yl) methyl] -2,4-dichloronicotinamide, (O85) N- [1 -(5-Bromo-3-chloropyridine-2-yl) ethyl] -2,4-dichloronicotinamide, (O86) N- [1- (5-bromo-3-chloropyridine-2-yl) ethyl] -2-Fluoro-4-iodonicotinamide, (O87) N-{(E)-[(cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2,3-difluorophenyl] methyl} -2-phenyl Acetamide, (O88) N-{(Z)-[(cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2,3-difluorophenyl] methyl} -2-phenylacetamide, (O89) N'-{ 4-[(3-tert-butyl-4-cyano-1,2-thiazole-5-yl) oxy] -2-chloro-5-methylphenyl} -N- Ethyl-N-methylimideformamide, (O90) N-methyl-2- (1-{[5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -N- (1,2,3,4-tetrahydronaphthalene-1-yl) -1,3-thiazole-4-carboxamide, (O91) N-methyl-2- (1-{[5-methyl-3-3) (Trifluoromethyl) -1H-pyrazole-1-yl] acetyl} piperidine-4-yl) -N-[(1R) -1,2,3,4-tetrahydronaphthalene-1-yl] -1,3- Thiazol-4-carboxamide, (O92) N-methyl-2- (1-{[5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidine-4-yl) -N -[(1S) -1,2,3,4-tetrahydronaphthalene-1-yl] -1,3-thiazole-4-carboxamide, (O93) pentyl {6-[({[(1-methyl-1H- Tetrazole-5-yl) (phenyl) methylene] amino} oxy) methyl] pyridine-2-yl} carbamate, (O94) phenazine-1-carboxylic acid, (O95) quinoline-8-ol, (O96) quinoline-8 -All sulfate (2: 1), (O97) tert-butyl {6-[({[(1-methyl-1H-tetrazole-5-yl) (phenyl) methylene] amino} oxy) methyl] pyridine-2- Il Carbamate, (O98) (5-bromo-2-methoxy-4-methylpyridine-3-yl) (2,3,4-trimethoxy-6-methylphenyl) methanone, (O99) N- [2-( 4-{[3- (4-chlorophenyl) propa-2-in-1-yl] oxy} -3-methoxyphenyl) tyl] -N2- (methylsulfonyl) valineamide, (O100) 4-oxo-4- [ (2-Phenylethyl) amino] butanoic acid, (O101) buta-3-in-1-yl {6-[({[(Z)-(1-methyl-1H-tetrazole-5-yl) (phenyl)) Methylene] amino} oxy) methyl] pyridine-2-yl} carbamate, (O102) 4-amino-5-fluoropyrimidine-2-ol (mutual variant: 4-amino-5-fluoropyrimidine-2 (1H)) -On), (O103) propyl 3,4,5-trihydroxybenzoate, (O104) [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridine-3-yl) methanol, (O105) (S)-[3- (4-chloro-2-fluorophenyl) -5 -(2,4-Difluorophenyl) -1,2-oxazol-4-yl] (pyridine-3-yl) methanol, (O106) (R)-[3- (4-chloro-2-fluorophenyl)- 5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridine-3-yl) methanol, (O107) 2-fluoro-6- (trifluoromethyl) -N- (1, 1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) benzamide, (O108) 2- (6-benzylpyridine-2-yl) quinazoline, (O109) 2- [6- (3- (3-) Fluoro-4-methoxyphenyl) -5-methylpyridine-2-yl] quinazoline, (O110) 3- (4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (O111) Absidic acid (O112) N'-[5-bromo-6- (2,3-dihydro-1H-inden-2-yloxy) -2-methylpyridine-3-yl] -N-ethyl-N- Methylimideformamide, (O113) N'-{5-bromo-6- [1- (3,5-difluorophenyl) ethoxy] -2-methylpyridine-3-yl} -N-ethyl-N-methylimideformamide , (O114) N'-{5-bromo-6-[(1R) -1- (3,5-difluorophenyl) ethoxy] -2-methylpyridine-3-yl} -N-ethyl-N-methylimide Formamide, (O115) N'-{5-bromo-6-[(1S) -1- (3,5-difluorophenyl) ethoxy] -2-methylpyridine-3-yl} -N-ethyl-N-methyl Imidformamide, (O116) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl) oxy] -2-methylpyridine-3-yl} -N-ethyl-N-methylimideformamide, (O117) ) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl) oxy] -2-methylpyridine-3-yl} -N-ethyl-N-methylimideformamide, (O118) N-cyclopropyl -3- (Difluoromethyl) -5-Fluoro-N- (2-Isopropylbenzyl) -1-Methyl-1H-Pyrazole-4-ka Luvoxamide, (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-cyclopropi-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-methyl) Benzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboki Samide, (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-cyclo Propyl-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-methylimideformamide, (O139) N'-{4-[(4,5-dichloro-1,3-thiazole-2-yl) oxy] -2,5-dimethylphenyl} -N- Ethyl-N-methylimideformamide, (O140) N- (4-chloro-2,6-difluorophenyl) -4- (2-chloro-4-fluorophenyl) -1,3-dimethyl-1H-pyrazole-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} propane-2-ol, (O143) 2-{2-[(7,8-difluoro-2-methylquinolin-3) -Il) oxy] -6-fluorophenyl} propa N-2-ol, (O144) 4- (2-chloro-4-fluorophenyl) -N- (2-fluorophenyl) -1,3-dimethyl-1H-pyrazole-5-amine, (O145) 4- (2-Chloro-4-fluorophenyl) -N- (2,6-difluorophenyl) -1,3-dimethyl-1H-pyrazole-5-amine, (O146) 4- (2-chloro-4-fluorophenyl) ) -N- (2-Chloro-6-fluorophenyl) -1,3-dimethyl-1H-pyrazole-5-amine, (O147) 4- (2-bromo-4-fluorophenyl) -N- (2-) Chloro-6-fluorophenyl) -1,3-dimethyl-1H-pyrazole-5-amine, (O148) N- (2-bromo-6-fluorophenyl) -4- (2-chloro-4-fluorophenyl) -1,3-dimethyl-1H-pyrazole-5-amine, (O149) 4- (2-bromo-4-fluorophenyl) -N- (2-bromophenyl) -1,3-dimethyl-1H-pyrazole- 5-Amine, (O150) 4- (2-bromo-4-fluorophenyl) -N- (2-bromo-6-fluorophenyl) -1,3-dimethyl-1H-pyrazole-5-amine, (O151) 4- (2-bromo-4-fluorophenyl) -N- (2-chlorophenyl) -1,3-dimethyl-1H-pyrazole-5-amine, (O152) N- (2-bromophenyl) -4- ( 2-Chloro-4-fluorophenyl) -1,3-dimethyl-1H-pyrazole-5-amine, (O153) 4- (2-chloro-4-fluorophenyl) -N- (2-chlorophenyl) -1, 3-Dimethyl-1H-pyrazole-5-amine, (O154) 4- (2-bromo-4-fluorophenyl) -N- (2,6-difluorophenyl) -1,3-dimethyl-1H-pyrazole-5 -Amine, (O155) 4- (2-bromo-4-fluorophenyl) -N- (2-fluorophenyl) -1,3-dimethyl-1H-pyrazole-5-amine, (O156) N'-(4) -{3-[(Difluoromethyl) sulfanyl] phenoxy} -2,5-dimethylphenyl) -N-ethyl-N-methylimideformamide, (O157) N'-(2,5-dimethyl-4- {3- [(1,1,2,2-Tetrafluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimideformamide, (O158) N'-(2,5-) Dimethyl-4- {3-[(2,2,2-trifluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimideformamide, (O159) N'-(2,5-dimethyl-4) -{3-[(2,2,3,3-tetrafluoropropyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimideformamide, (O160) N'-(2,5-dimethyl-4-) {3-[(Pentafluoroethyl) sulfanyl] phenoxy} phenyl) -N-ethyl-N-methylimideformamide, (O161) N'-(4-{[3- (difluoromethoxy) phenyl] sulfanyl} -2, 5-Dimethylphenyl) -N-ethyl-N-methylimideformamide, (O162) N'-(2,5-dimethyl-4-{[3- (1,1,2,2-tetrafluoroethoxy) phenyl] Sulfanyl} phenyl) -N-ethyl-N-methylimideformamide, (O163) N'-(2,5-dimethyl-4-{[3- (2,2,2-trifluoroethoxy) phenyl] sulfanyl} phenyl ) -N-Ethyl-N-Methylimideformamide, (O164) N'-(2,5-dimethyl-4-{[3- (2,2,3,3-tetrafluoropropoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimideformamide, (O165) N'-(2,5-dimethyl-4-{[3- (pentafluoroethoxy) phenyl] sulfanyl} phenyl) -N-ethyl-N-methylimide Homiamide, (O166) 2- [3,5-bis (difluoromethyl) -1H-pyrazole-1-yl] -1- [4- (4- {5- [2- (propa-2-in-1) -Iloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazole-2-yl) piperidin-1-yl] etanone, (O167) 2- [3,5 -Bis (difluoromethyl) -1H-pyrazole-1-yl] -1- [4- (4- {5- [2-fluoro-6- (propa-2-in-1-yloxy) phenyl] -4, 5-Dihydro-1,2-oxazol-3-yl} -1,3-thiazole-2-yl) piperidin-1-yl] etanone, (O168) 2- [3,5-bis (difluoromethyl) -1H -Pyrazole-1-yl] -1- [4- (4- {5- [2-chloro-6- (propa-2-in-1-yloxy) phenyl] -4] -4 , 5-Dihydro-1,2-oxazol-3-yl} -1,3-thiazole-2-yl) piperidin-1-yl] etanone, (O169) 2-{3- [2- (1-{[ 3,5-bis (difluoromethyl) -1H-pyrazole-1-yl] acetyl} piperidin-4-yl) -1,3-thiazole-4-yl] -4,5-dihydro-1,2-oxazol- 5-yl} phenylmethanesulfonate, (O170) 2-{3- [2-(1-{[3,5-bis (difluoromethyl) -1H-pyrazole-1-yl] acetyl} piperidin-4-yl)) -1,3-Thiazole-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} -3-chlorophenylmethanesulfonate, (O171) 2- [3,5-bis (difluoromethyl) -1H-Pyrazole-1-yl] -1- [4- (4-{(5S) -5- [2- (propa-2-in-1-yloxy) phenyl] -4,5-dihydro-1, 2-Oxazole-3-yl} -1,3-thiazole-2-yl) piperidin-1-yl] etanone, (O172) 2- [3,5-bis (difluoromethyl) -1H-pyrazole-1-yl) ] -1- [4- (4- {(5R) -5- [2- (propa-2-in-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazole-2-yl) piperidin-1-yl] etanone, (O173) 2- [3,5-bis (difluoromethyl) -1H-pyrazole-1-yl] -1- [4-( 4-{(5S) -5- [2-Fluoro-6- (propa-2-in-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3 -Thiazol-2-yl) piperidin-1-yl] etanone, (O174) 2- [3,5-bis (difluoromethyl) -1H-pyrazole-1-yl] -1- [4- (4-{( 5R) -5- [2-Fluoro-6- (propa-2-in-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3-thiazole-2 -Il) piperidin-1-yl] etanone, (O175) 2- [3,5-bis (difluoromethyl) -1H-pyrazole-1-yl] -1- [4- (4- {(5S) -5) -[2-Chloro-6- (propa-2-in-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl}- 1,3-thiazole-2-yl) piperidin-1-yl] etanone, h (O176) 2- [3,5-bis (difluoromethyl) -1H-pyrazole-1-yl] -1- [4- ( 4-{(5R) -5- [2-Chloro-6- (propa-2-in-1-yloxy) phenyl] -4,5-dihydro-1,2-oxazol-3-yl} -1,3 -Thiazol-2-yl) piperidin-1-yl] etanone, (O177) 2-{(5S) -3- [2- (1-{[3,5-bis (difluoromethyl) -1H-pyrazole-1) -Il] acetyl} piperidine-4-yl) -1,3-thiazole-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} phenylmethanesulfonate, (O178) 2-{(O178) 2-{( 5R) -3- [2- (1-{[3,5-bis (difluoromethyl) -1H-pyrazole-1-yl] acetyl} piperidine-4-yl) -1,3-thiazole-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} phenylmethanesulfonate, (O179) 2-{(5S) -3- [2- (1-{[3,5-bis (difluoromethyl)) -1H-pyrazole-1-yl] acetyl} piperidine-4-yl) -1,3-thiazole-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} -3-chlorophenylmethane Ssulfonate, (O180) 2-{(5R) -3- [2- (1-{[3,5-bis (difluoromethyl) -1H-pyrazole-1-yl] acetyl} piperidin-4-yl) -1 , 3-Thiazole-4-yl] -4,5-dihydro-1,2-oxazol-5-yl} -3-chlorophenylmethanesulfonate, (O181) (3S, 6S, 7R, 8R) -8-benzyl- 3- {3-[(Isobutyryloxy) methoxy] -4-methoxypicolinamide} -6-methyl-4,9-dioxo-1,5-dioxonan-7-ylisobutyrate.

As described above, the compound of formula (I) can be mixed with one or more compatible active compounds selected from the class of insecticide / acaricide / nematode repellent. The active ingredient from the class of insecticides / tick repellents / nematicides is described herein, for example, in The Pesticide Manual 17th Ed. Known and described in, or specified by their common names that can be searched on the Internet (eg, at www.alanwood.net/pesticides).

(1) Acetylcholinesterase (AChE) inhibitors such as carbamates such as aranicalve, aldicalb, benziocarb, benfuracarb, buttocarboxym, butoxycarboxym, carbalyl, carbofuran, carbosulfane, ethiophencarb, phenoccarb, formethanate, fratiocarb, isoprocarb, Metiocarb, Metmil, Metlucalve, Oxamil, Pyrimicalve, Propoxul, Thiodicarb, Thiophanox, Triazamate, Trimethacarb, XMC and Xylylcarb, or organic phosphates such as acetyl, azamethiphos, azinephos-ethyl, azinephos-methyl, cassaphos, chlorpyrifos, chlorpyrifos. , Chlorpyrifos, Chlorpyrifos, Chlorpyrifos-Methyl, Coomass, Cyanophos, Demeton-S-Methyl, Diadinone, Dichlorvos / DDVP, Diclotophos, Dimethate, Dimethylbinphos, Disulfoton, EPN, Ethion, Etoprophos, Famfur, Phenamiphos, Fenitrothion, Fention , Heptenophos, Imiciaphos, Isophenphos, Isopropyl O- (methoxyaminothio-phosphoryl) salicylate, isoxathione, malathion, mecarbam, methamidophos, metidathion, mevinphos, chlorpyrifos, naredo, ometoate, oxydemethone-methyl, parathion, parathion-methyl, fentoate, Holate, Hosalon, Hosmet, Phosphamiden, Hoxime, Pyrimiphos-methyl, Prophenofus, Propetanphos, Prothiophos, Pyraclophos, Pyridafenthion, Kinalphos, Sulfotep, Tebupyrimphos, Temephos, Telbuhos, Tetrachlorbinphos, Thiometon, Triazophos, Trichlorfon and Bamidthione.

(2) GABA open / close chlorine channel antagonists, such as cyclodiene organic chlorin systems, such as chlordan and endosulfan or phenylpyrazole (fiprol), such as etiprol and fipronil.

(3) Sodium channel modulator / potential-dependent sodium channel blocker, for example, pyrethroids, such as acrinathrin, aletrin, d-cis-trans aletrin, d-trans aletrin, bifentrin, bioaletrin, bioaletrin S-cyclopentenyl isomer, Bioresmethrin, Cycloprothrin, Cypermethrin, Beta-Cypermethrin, Cypermethrin, Lambda-Cypermethrin, Gamma-Cypermethrin, Cipermethrin, Alpha-Cypermethrin, Beta-Cypermethrin, Theta-Cypermethrin, Zeta-Cypermethrin, Ciphenothrin [(1R) ) -Trans-isomer], deltamethrin, empentrin [(EZ)-(1R) -isomer], esphenvalerate, etofenprox, phenpropathrin, fenvalerate, flucytrinate, flumethrin, tau-fluvalinate, Halphenprox, imiprothrin, cadetrin, monfluorothrin, permethrin, phenothrin [(1R) -trans-isomer)], prarethrin, pyrethrins (pyrethrin), lesmethrin, cypermethrin, tefluthrin, tetramethrin, tetramethrin [(1R) -isomer) Body)], tralomethrin and transfluthrin or DDT or methoxychlor.

(4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, such as neonekotinoids, such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradiflon.

(5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators, such as spinosins, such as spinetram and spinosad.

(6) Glutamic acid open / close chlorine channel (GluCl) allosteric modulators, such as avermectin / milbemycin, such as abamectin, emamectin benzoate, lepimectin and milbemectin.

(7) Juvenile hormone-like agents such as juvenile hormone analogs such as hydroprene, quinoprene and methoprene or phenoxycarb or pyriproxyfen.

(8) Active compounds with unknown or non-specific mechanisms of action, such as alkyl halides (eg, methyl bromide and other alkyl halides), or chloropicrin or fluoride or borates or talites. Or a methyl isocyanate generator.

(9) Notochord TRPV channel modulators, such as pyridineazomethine derivatives, such as pimetrodin and pyrifluquinazone or flonicamid.

(10) Tick growth inhibitors such as clofentezine, hexitiazox and difluorovidazine or etoxazole.

(11) Insect intestine Intestinal microbial disturbant, for example, Bacillus thuringiensis subspecies islaelensis, Bacillus thuringiensis subspecies Islaelensis, Bacillus thuringiensis sis sis Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies Teneblionis (Bacillus thuringiensiss subspirices tenebrises) and Bacillus Sfacillus Vip3a, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1.

(12) Inhibitors of mitochondrial ATP synthase, such as organic tint tick repellents, such as azocyclotin, cyhexatin and fenbutatin oxide or diafenthiuron or propargite or tetradiphon.

(13) Oxidative phosphorylation uncouplers that act through disruption of the proton gradient, such as chlorfenapyr, DNOC and sulfluramide.

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

(15) Inhibitors of chitin biosynthesis (type 0), such as bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxyuron, hexaflumron, lufenuron, novallon, nobiflumron, teflubenzuron and triflumron.

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

(17) Molting perturbants (especially in Diptran), such as cyromazine.

(18) Ecdysone receptor agonists such as chromaphenozide, halophenozide, methoxyphenozide and tebufenozide.

(19) Octopamine receptor agonists such as Amitraz.

(20) Mitochondrial Complex III Electron Transfer Inhibitors, such as hydramethylnon or acequinosyl or fluaclipirim or biphenazate.

(21) Mitochondrial Complex I Electron Transfer Inhibitors, such as METI tick repellents and insecticides, such as phenazaquin, phenpyroximate, pyrimidifen, pyridaben, tebufenpyrado and tolfenpyrado or rotenone (Delis).

(22) Voltage-gated sodium channel blockers, such as indoxacarb or metaflumison.

(23) Inhibitors of acetyl-CoA carboxylase, such as tetrolic acid and tetramic acid derivatives, such as spirodiclofen, spiromesiphen and spirotetramate.

(24) Mitochondrial complex IV electron transfer inhibitors such as phosphides such as aluminum phosphide, calcium phosphide, zinc phosphide and phosphide or cyanide.

(25) Mitochondrial Complex II Electron Transfer Inhibitors, such as beta-ketonitrile derivatives, such as sienopyraphen and siflumethofen or carboxyanilide.

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

(29) Chordotonal organ regulators for undefined target sites, such as flonicamid.

Additional active ingredients with unknown or uncertain modes of action, such as afidopyropen, ahoxolanel, azadilactin, bencrothias, benzoximate, biphenazate, brofuranilide, bromopropylate, quinomethionate, glacial stone, cyclaniliprol, cycloxapride, cihalodiamide. , Dichloromesothiaz, dicohol, difluorovidazine, fromotkin, fluazindrindin, fluenesulfone, fluphenerim, fluphenoxystrobin, fluphyllol, fluhexaphone, fluopirum, flularanel, fluxametamid, fuphenozide, guadipill, heptafluthrin, imidacrotiz , Rotylanel, Meperfluthrin, Pyconguzing, Pifrubmid, Pyridaryl, Pyrifluquinazone, Pyriminostrobin, Saroranel, Tetramethylfluthrin, Tetranipiplol, Tetrachloranthraniliprol, Thioxazaphen, Triflumezopyrim and Iodomethane; Preparations based on Filmus (I-1582, BioNeem, Votivo), and the following known active compounds: 1- {2-fluoro-4-methyl-5-[(2,2,2-tri). Fluoroethyl) sulfinyl] phenyl} -3- (trifluoromethyl) -1H-1,2,4-triazole-5-amine (known from WO2006403635), {1'-4 [(2E) -3- (4-) Chlorophenyl) propa-2-ene-1-yl] -5-fluorospiro [indole-3,4'-piperidin] -1 (2H) -yl} (2-chloropyridine-4-yl) metanone (known from WO2003106457) ), 2-Chloro-N- [2- {1-[(2E) -3- (4-chlorophenyl) propa-2-en-1-yl] piperidine-4-yl} -4- (trifluoromethyl) Phenyl] Isonicotinamide (known from WO2006003494), 3- (2,5-dimethylphenyl) -4-hydroxy-8-methoxy-1,8-diazaspiro [4.5] deca-3-en-2-one ( (Known from WO200949851), 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1,8-diazaspiro [4.5] deca-3-en-4-ylethyl carbonate (known from WO200949851) , 4- (Buta-2-in-1-yloxy) -6 -(3,5-dimethylpiperidin-1-yl) -5-fluoropyrimidine (known from WO200499160), 4- (but-2-in-1-yloxy) -6- (3-chlorophenyl) pyrimidin (known from WO2003076415) ), PF1364 (CAS registration number 1204776-60-2), methyl-2- [2-({[3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazole-5-yl] carbonyl] } Amino) -5-Chloro-3-methylbenzoyl] -2-methylhydrazine carboxylate (known from WO2005085216), methyl-2- [2-({[3-bromo-1- (3-chloropyridin-2-) Il) -1H-pyrazole-5-yl] carbonyl} amino) -5-cyano-3-methylbenzoyl] -2-ethylhydrazine carboxylate (known from WO2005085216), methyl-2- [2-({[3-] 3- Bromo-1- (3-chloro-pyridin-2-yl) -1H-pyrazole-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-pyrazole-5-yl] carbonyl} amino) benzoyl]- 2-Ethylhydrazine carboxylate (known from WO2005085216), N- [2- (5-amino-1,3,4-thiazylazole-2-yl) -4-chloro-6-methylphenyl] -3-bromo-1 -(3-Chloropyridin-2-yl) -1H-pyrazole-5-carboxamide (known from CN1020579225), 4- [5- (3,5-dichlorophenyl) -5- (trifluoromethyl) -4,5- Dihydro-1,2-oxazol-3-yl] -2-methyl-N- (1-oxide thietan-3-yl) benzamide (known from WO2009080250), N-[(2E) -1-[(6--) Chloropyridin-3-yl) methyl] Pyridine-2 (1H) -iriden] -2,2,2-trifluoroacetamide (known from WO2012029672), 1-[(2-chloro-1,3-thiazole-5-) Il) Methyl] -4-oxo-3-phenyl-4H-pyrido [1,2-a] pyrimidin-1-ium-2-oleate (publicly available 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] deca-1-en-1-yl] carbonate ( 3 (E) -3- [1-[(6-chloro-3-pyridyl) methyl] -2-pyridylidene] -1,1,1-trifluoropropane-2-one (disclosed in CN102060818) (Known from WO2013144213), N- (Methylsulfonyl) -6- [2- (Pyridine-3-yl) -1,3-thiazole-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 WO20100051926).

The compound of formula (I) may be used to treat some fungal pathogens. Non-limiting examples of fungal disease pathogens that can be treated by the present invention include:
Diseases caused by the following powdery mildew pathogens, eg, species of the genus Blumeria, eg, Blumeria graminis; species of the genus Podosphaera, eg, podosphaera leucotrica; species of the genus Sphaeroteca, eg. Sphaerotheca fuliginea; species of the genus Powderysiphe, such as Uncinulla necator; species of the genus Erysiphe, such as Erysiphe cychoraceau;
Diseases caused by: Genus species, such as Phakopsora pachyrhiji or Phakopsora meibomiae; Puccinia species, such as Puccinia recondita (Puccinia) striiformis); species of the genus Puccinia, eg, Uromyces apendiculatus;
Diseases caused by pathogens derived from the following groups of oomycetes, eg, species of the genus Albugo, eg, Albugo candida; species of the genus Bremia; eg, species of the genus Bremia lactucae; For example, Peronospora pisi or P. brassicae; species of the genus Phytophthora; for example, Phytophthora infestans; species of the genus Plasmopara, such as Plasmopara. Species of the genus Pseudonospora, such as Pseudoperonospora humuli or Pseudoperonospora cubensis; Species of the genus Pythium, such as Pythium.
Leaf blight and wilt caused by, for example, species of the genus Alternaria; eg Alternaria solani; species of the genus Cochliobolus; eg, species of the genus Cochliobolus; For example, Cradiosporium cucumerinum; species of the genus Cochliobolus, such as Cochliobolus sativus (species morphology: Drexlera, nickname: Cochliobolus); or Cochliobolus. cochliobolus; species of the genus Cochliobolus, eg, Cochliobolus lindemutanium; species of the genus Cycloconium, eg, species of the genus Cycloconium oleaginum (genus Cycloconium oleaginum; Species such as Elsinoe fawcettii; species of the genus Cochliobolus, such as Cochliobolium laeticolor; species of the genus Cochliobolus, such as Glomerella singlati; Glomerla Genus species, such as Guignardia bidwelli; species of the genus Cochliobolus, eg, Leptosphaeria maculans; species of the genus Cochliobolus, eg, genus Cochliobolus. Species of the genus Cochliobolus (Microdochium nivale); species of the genus Cochliobolus (eg, Mycosphaerella glaminicola), Cochliobolera arachijicola (Mycosphaerella) Species, such as Faeos faeria nodolm (Phaeo) Septoria nodolum); species of the genus Pyrenohora, such as Pyrenophora teres or Pyrenophora tritici repentis; species of the genus Lamlaria, eg, lumaria colo. Lumularia areola; species of the genus Lincosporium, eg, Rynchosporium secalis; species of the genus Septoria, eg Septoria apii or Septoria licoperci (Septoria). Species of the genus Septoria, such as Septoria nodolum; species of the genus Septoria, such as Typhula incarnata; species of the genus Benzria, such as Venturia inaq.
Diseases of the roots and stems caused by, for example, species of the genus Cortisium; eg Corticium graminearm; species of the genus Fusalium; eg, species of the genus Fusarium oxysporum; species of the genus Gaeumannomises, eg. , Gaeumannomyces graminis; species of the genus Plasmodiophora, such as Plasmodiophora brassicae; species of the genus Rizoctonia, such as the genus Rizoctonia solani (Rhizo). For example, Sarocladium oryzae; species of the genus Sclerotium, such as Sarocladium oryzae; species of the genus Tapesia, such as the genus Tapesia acuformis, genus Tapesia acuformis; basicola); species of the genus Ganoderma, such as Ganoderma lucidum;
Ear diseases caused by: eg, species of the genus Alternaria, eg, species of the genus Alternaria; species of the genus Aspergillus, eg, Aspergillus flavus; Species of the genus Cladosporium cladosporioides; species of the genus Claviceps, for example, species of the genus Fusarium; for example, species of the genus Fusarium; Species such as Gibbella zeae; species of the genus Monografera, such as Monografella nivalis; species of the genus Stagnospora, such as Stagnospora no.
Diseases caused by the following scab fungi, such as species of the genus Sphacelloteca, such as Sphacellotheca reiliana; species of the genus Tilletia, such as Tilletia caries or Tilletia controversa. Species of the genus Tilletia, such as Urosistis occulta; species of the genus Ustilago, such as Ustilago nuda;
Fruit spoilage caused by, for example, species of the genus Aspergillus, such as Aspergillus flavus; species of the genus Botrytis, such as Botrytis sinerea; species of the genus Penicillium, such as Penicillium expansum. (Penicillium expansum) or Penicillium purpurogenum; species of the genus Rezopus, such as Rhizopus stolonifer; species of the genus Sclerotinia, such as Sclerotini screlotini -Verticillium album;
Seed- and soil-mediated rot and wilt and also seed disease caused by, for example, species of the genus Alternaria, eg Alternaria brassicicola; species of the genus Afanomyces, eg Afanomyces. Aphanomyces euteiches; species of the genus Ascokita, eg, Ascochyta lentis; species of the genus Aspergillus, eg, species of the genus Aspergillus flavus; species of the genus Cladosporium, eg. (Cladosporium herbarum); species of the genus Cocriobolus, eg, Cocriobolus satibus (species morphology: genus Drexlera, nicknamed Bipolaris: genus Helmintsporium); species of the genus Collettricum, eg, collettricome Species of the genus Fusalium, eg, Fusalium krumorm; Species of the genus Giberella, eg, Gibelera Zeae; Species of the genus Macrohomina, eg, Macrophomina phaseolina; Genus species such as Monographera nivalis; Penicillium species such as Penicillium expansum; Poma species such as Poma lingam; Homapsis species such as Homopsis sojae Species of the genus Phytophthora, such as Phytophthora cactorum; Species of the genus Preospora, such as Pyrenophora graminea; For example, Pythium ultimum; species of the genus Rezoctonia, such as lysoctonia solani; species of the genus Ryzopus; , For example, Septoria Nodolm nodorum); species of the genus Chikhura, eg, Chikhura incarnata; species of the genus Verticillium, eg, Verticillium dahliae;
Cancer disease, hump and witches' broom disease, eg, species of the genus Nextria, eg, Nectria galligena; caused by:
Wilt disease caused by, for example, species of the genus Monilinia, such as Monilinia laxa;
Leaf, flower and fruit malformations caused by, for example, species of the genus Exovasidium, eg, Exobasideium vexans; species of the genus Taphrina, eg, Taphrina deformans;
Declining diseases of woody plants caused by, for example, species of the genus Ganoderma, such as Phaemoniella clamydospora, Phaeoacremonium aleofilm or Fomitipolia elaeofilum Species of the genus, such as Ganoderma boninense;
Flower and seed diseases caused by, for example, species of the genus Botrytis, such as Botrytis cinerea;
Diseases of plant tubers caused by, for example, Rhizoctonia species, eg Rhizoctonia solani; Helminthosporium genus species, eg Helminthosporium solani;
Diseases caused by the following bacterial pathogens, such as species of the genus Xanthomonas, such as Xanthomonas campestris pv. Xanthomonas campestris pv. Oryzae; species of the genus Pseudomonas, such as Pseudomonas syringae pv. Pseudomonas syringae pv. Lachrymans; species of the genus Erwinia, eg Erwinia amylovora; species of the genus Ralstonia, eg Ralstonia solan
Fungal diseases of the root and stem base caused by, for example, black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina), red mold or fusarium wilt. As well as pods and terrestrial rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equectum, Fusarium root rot, Fusarium root rot) Mycoleptodiscus terrestris, Neocosmospora basinfecta, Sheath and stalk blight (Diaporte phaseola stalk Fusarium) phasolerum var. Caulivora), phytofutra rot (Phytophthora megasperma), deciduous disease (Phialophora gregata), phylophora gregata, phythium rot Pythium irregulare, Pythium devarianum, Pythium myriotylum, Phythium ultimum (Pythium ultilum and scab, Fusarium root rot, Fusarium rot) Stem rot (Sclerotinia sclerotiorum), Sclerotinia white silk disease (Sclerotinia lorfsii), Thieraviopsis root rot (Chierabiopsis basicola) tis.

Plants that can be treated according to the present invention include: rose family plants (eg, fruit seeds such as apples, pears, apricots, cherries, almonds and peaches), Ribesioidae plants, walnuts plants, mosquito plants, Urushi family plants, beech family plants, mulberry family plants, mokusei family plants, matatabi family plants, kusunoki family plants, basho family plants (eg banana trees and plantation plants), madder family plants (eg coffee), camellia family plants , Blue-green algae, citrus plants (eg, lemons, oranges and grapefruits); vines (eg, grapes); eggplants (eg, tomatoes, peppers), lilies, citrus (eg,) , Lettuce), Seri family plant, Abranaceae plant, Red lizard family plant, Uri family plant (eg cucumber), Negi family plant (eg Leeki, onion), Bean family plant (eg pea); Rice family (Poaceae) Major crop plants such as sp.) / Gramineae sp. (For example, maize, shiva, grain (such as wheat, lime, rice, barley, oat wheat, millet and rye wheat)), and plants of the family Kiku (eg, sunflower). , Abranaceae plants (eg, white cabbage, red cabbage, broccoli, cauliflower, sprout cabbage, chingensai, korurabi, radish, and rapeseed, pearl oyster, horse radish and cress), fabacae sp. ), Papilionaceae sp. (eg, soybean), eggplant family plant (eg potato), red azalea family plant (eg sugar daikon, feed beet, fudansou, beet root); ); Useful and ornamental plants for gardens and forests; as well as genetically modified varieties of each of these plants.

All plants and parts of all plants can be treated according to the present invention. Plants are here understood to mean all plants and all plant populations, such as desirable and undesired wild plants or crop plants (including natural crop plants). Crop plants include transgenic plants, as well as cultivars that can and cannot be protected by the rights of plant breeders, by conventional breeding and optimization methods, or by bioengineering and genetic engineering methods. Alternatively, it can be a plant that can be obtained by a combination of these methods. Plant parts are understood to mean all parts and organs of above-ground and underground plants such as shoots, leaves, flowers and roots, examples of which are leaves, needles, stalks, stems, leaves and fruits. Includes body, fruits and seeds, as well as roots, bulbs and rhizomes. Plant parts also include harvested materials, as well as vegetative and reproductive materials such as cuttings, tubers, rhizomes, scions and seeds.

The present invention relates to seeds, in particular seeds treated with at least one of the compounds of formula (I) and a composition thereof (during dormancy, after undercoating, before germination, or even when roots and leaves are present. ) Is further included. The seeds of the present invention are used as a method for protecting seeds and plants germinated from seeds from phytopathogenic harmful fungi. In these methods, seeds treated with at least one active ingredient of the invention are used.

Seeds, sprouting plants and sprouted seedlings are used so that the active ingredients used do not damage the plant itself, but provide the best possible protection from attack by phytopathogenic fungi. It is also desirable to optimize the amount of active ingredient to be produced. In particular, seed treatment methods should also take into account the unique phenotype of transgenic plants in order to minimize the use of crop protection compositions and achieve optimal protection of seeds and germinating plants. ..

Accordingly, the invention also relates to a method of protecting seeds, germinating plants and germinated seedlings from attack by animal pests and / or phytopathogenic pests by treating the seeds with the compositions of the invention. .. The invention also relates to the use of compositions according to the invention for treating seeds to protect seeds, germinated plants and germinated seedlings from animal pests and / or phytopathogenic microorganisms. The invention further relates to seeds treated with the compositions of the invention to protect against animal pests and / or phytopathogenic microorganisms.

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 pests. .. In this way, the plant is protected by immediate treatment of the crop at or immediately after sowing and seed treatment before sowing. The active ingredient or composition of the invention can also be used, among other things, in transgenic seeds, where plants grown from this seed act against pests, herbicide damage or abiotic stress. The advantage of being able to express a protein is also conceivable. Treatment of such seeds with the active ingredient or composition of the invention, such as insecticidal proteins, can result in the control of certain pests. Surprisingly, additional synergies can be observed in this case, which further enhances the effectiveness of protection from attacks by pests, microorganisms, weeds or abiotic stress.

The compound of formula (I) is suitable for the protection of seeds of any plant variety used in agriculture, greenhouses, forests or horticulture. More specifically, seeds are grains (such as wheat, barley, rye, millet and oat), rapeseed, maize, cotton, soybeans, rice, potatoes, sunflowers, beans, coffee, beets (eg, sugar cane and fodder beets). ), Peanuts, vegetables (tomatoes, ryes, onions and lettuce, etc.), lawn and ornamental plant seeds. Treatment of wheat, soybean, rapeseed, maize and rice seeds is of particular importance.

As also described below, treatment of transgenic seeds with the active ingredient or composition of the invention is of particular importance. Transgenic seeds refer to, for example, plant seeds containing at least one non-homologous gene that allows the expression of a polypeptide or protein with pesticidal properties. Such non-homologous genes in transgenic seeds can be derived, for example, from microorganisms of species of the genera Bacillus, Resovium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. These non-homologous 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 root worm. In particular, preferably, the non-homologous gene is derived from Bacillus turingiensis.

In the context of the invention, the compositions of the invention are applied either alone or in a suitable formulation. Preferably, the seeds are treated in a sufficiently stable condition so that they are not damaged during the treatment process. In general, seeds can be processed at any time between harvest and some time after sowing. It is customary to use seeds isolated from the plant and seeds removed from the cob, shell, stalk, skin, hair or pulp of the fruit. For example, it is possible to use seeds that have been harvested, washed and dried to a moisture content of less than 15% by weight. Alternatively, after drying, for example, treated with water and then re-dried, or seeds immediately after undercoating, or seeds stored under undercoating conditions, or pre-germinated seeds, or on nursery trays, tape or paper. It is also possible to use sown seeds.

When treating seeds, the amount of the composition of the invention and / or the amount of additional additives applied to the seeds is selected so as not to harm the germination of the seeds, or the resulting plant It should generally be ensured that it will not be damaged. This must be ensured, especially in the case of active ingredients that can exhibit phytotoxic effects at certain doses.

The compounds of formula (I) can be applied directly, i.e., without any other constituents and without dilution. In general, it is preferable to apply the composition to seeds in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those of skill in the art. The compound of formula (I) can be converted into a conventional formulation related to seed surface application, such as a solution, an emulsion, a suspension, a powder, a foam, or a slurry, or film formation. It can be combined with other coating compositions of seeds such as sex substances, pellet-forming substances, fine iron or other metal powders, granules, coating materials that inactivate seeds, and even ULV formulations.

In the treatment of seeds to facilitate plantability, the seeds can be coated with a polymer. Polymer coatings consist of binders, waxes and pigments, as well as one or more stabilizers in an effective amount 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 anhydride maleic acid or butadiene styrene. can. Other similar polymers can also be used.

These formulations are composed of active ingredients or combinations of active ingredients and conventional additives such as conventional bulking agents and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, two. It is prepared by a known method by mixing with a next thickener, an adhesive, gibererin and also water.

The useful pigments that can be present in the seed powder coating formulations that can be used according to the present invention are all of the pigments that are conventional for such purposes. Either a pigment that is slightly soluble in water or a water-soluble pigment can be used. For example, Rhodamine B, C.I. I. Pigment Red 112 and C.I. I. Contains a dye known by the name Solvent Red 1.

The useful wetting agents that can be present in the seed powder coating formulations that can be used according to the present invention are all substances that promote wetting and are commonly used in the formulation of active pesticide components. Alkylphthalene sulfonates such as diisopropylnaphthalene sulfonate or diisobutylphthalene sulfonate can be used preferentially.

Useful dispersants and / or emulsifiers that can be present in the seed powder coating formulations available according to the invention are nonionic, anionic and cationic formulations commonly used in the formulation of active pesticide components. All of the dispersants. Nonionic or anionic dispersants, or mixtures of nonionic or anionic dispersants, can be used preferentially. Useful nonionic dispersants include, among other things, ethylene oxide / propylene oxide block polymers, alkylphenol polyglycol ethers and tristyrylphenol polyglycol ethers, and their phosphorylated or sulfated derivatives. Suitable anionic dispersants are, among other things, lignosulphonates, polyacrylic acids and arylsulphonic acid / formaldehyde condensates.

The defoaming agents that can be present in the seed powder coating formulations that can be used according to the present invention are all foaming inhibitors commonly used in the formulations of active pesticide components. Silicone defoamers and magnesium stearate may be used preferentially.

The preservatives that can be present in the seed powder coating formulations that can be used according to the present invention are all substances that can be used for such purposes in pesticide compositions. Examples include dichlorophen and benzyl alcohol hemiformal.

The secondary thickeners that can be present in the seed powder coating formulations that can be used according to the present invention are all substances that can be used for such purposes in pesticide compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan, modified clay and finely ground silica.

The adhesives that can be present in the seed powder coating formulations that can be used according to the present invention are all of the conventional binders that can be used in seed powder coating products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

The formulations for seed surface application available according to the invention can be used to treat a wide variety of seeds, either directly or after pre-dilution with water. For example, concentrates, or preparations that can be obtained from concentrates by diluting with water, are seeds of grains such as wheat, barley, rye, oat and rye wheat, as well as maize, soybean, rice, rapeseed, peas, etc. It can be used to coat rye, cotton, sunflower and beet seeds, or a wide variety of vegetable seeds. The formulations available according to the invention, or diluted preparations thereof, can also be used for seeds of transgenic plants. In this case, additional synergies may also occur during interaction with the substance formed by expression.

For the treatment of seeds with the formulations available according to the invention, or the formulations prepared from the formulations by the addition of water, all mixing units routinely usable for seed surface application are useful. be. Specifically, the procedure for seed surface application is to put the seed in a mixer, add a specific desired amount of the pharmaceutical product as it is or after pre-diluting with water, and all the applied pharmaceutical products are on the seed surface. Mix everything until it is evenly distributed. If appropriate, this is followed by a drying operation.

The dosages of the formulations that can be used according to the present invention can vary over a relatively wide range. The application dose is guided by the specific content of the active ingredient in the formulation and by the seeds. The application rate of each single active ingredient is generally between 0.001 and 15 g per kilogram of seeds, preferably between 0.01 and 5 g per kilogram of seeds.

When the compound of formula (I) is used as a fungicides, the application dose can vary over a relatively wide range, depending on the type of application. The application dose of the active ingredient of the present invention is as follows:
For treatment of plant parts, eg leaves: 0.1-10000 g / ha, preferably 10-1000 g / ha, more preferably 30-300 g / ha (when applied by watering or drip, especially rock wool or perlite, etc. It is even possible to reduce the application rate when using the inert substrate of);
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: 0.1-10000 g / ha, preferably 1-5000 g / ha
Is.

These doses are merely examples and are not limited to the purposes of the present invention.

In some cases, the compound of formula (I) may be used as a herbicide, fungicide, growth regulator, or agent to improve plant properties, or as a microbial killing agent, at a particular concentration or dose. For example to be used as fungicides, antifungal agents, antibacterial agents, antiviral agents (including compositions against willoids), or as compositions against MLOs (mycoplasma-like organisms) and RLOs (rickettsia-like organisms). You can also.

The compound of formula (I) interferes with the physiological process of the plant and can therefore also be used as a plant growth regulator. Plant growth regulators can exert various effects on plants. The action of this substance is essentially dependent on the stage of plant development, the time of application with respect to the plant variety, and also 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 particular desired effect on the crop plant.

Growth-regulating effects include faster germination, better germination, improved root system and / or root growth, improved seeding ability, more effective seeding, early blooming, plant length and / or biomass. Increase, stem shortening, improvement of shoot growth, number of seeds / ears, number of ears / m ² , number of buds and / or number of flowers, increase in yield index, larger leaves, reduction of basal leaves, Includes improved foliage, early ripening / early fruit finish, uniform ripening, increased ripening period, better fruit finish, larger fruit / vegetable size, reduced germination resistance and lodging.

Increased or improved yields include total biomass per hectare, yield per hectare, seed / fruit weight, seed size and / or hectolitre weight, and:
Improved processability with respect to size distribution (silage, fruit, etc.), uniform ripening, grain moisture, good milling, good brewing, good beer brewing, increased fruit juice yield, harvestability, digestibility, sedimentation value Includes, falling number, sheath stability, storage stability, improved fiber length / strength / homogeneity, improved milk and / or meat quality of silage-reared animals, adaptability to cooking and frying, etc.
Fruit / grain quality, improved size distribution (seed, fruit, etc.), improved storage / shelf life, elasticity / softness, taste (fragrance, texture, etc.), grade (size, shape, number of berries, etc.), Further includes marketability improvements related to number of berries / fruits per bundle, freshness, freshness, wax coverage, frequency of physiological injuries, color tones, etc.
For example, protein content, fatty acid, oil content, oil quality, amino acid composition, sugar content, acid content (pH), sugar / acid ratio (Brix meter), polyphenol, starch content, nutritional quality, gluten content. / Further includes an increase in desired ingredients such as index, energy content, taste, etc.
Further including reductions in unwanted components such as less mycotoxins, less aflatoxins, geosmine levels, phenolic aromas, laccases, polyphenol oxidases and peroxidases, nitrate content, etc.
Refers to improving the quality of products.

Plant growth-regulating compounds can be used, for example, to slow down the vegetative growth of plants. Thus, for example, in the case of grass, such a decline in growth can reduce the frequency of mowing in gardens of foliage plants, parks and sports facilities, roadsides, airports, or in fruit crops. Highly interested. Similarly, it is important to control the growth of herbaceous and woody plants by the side of the road and near pipelines or overhead cables, or very generally, in areas where active plant growth is not desired. Is.

Similarly, the use of growth regulators is important because it inhibits the longitudinal growth of grains. This reduces or completely eliminates the risk of pre-harvest plant lodging. In addition, growth regulators in the case of cereals can enhance the culm, which also prevents lodging. By using growth regulators to shorten and strengthen the culm, higher fertilizer amounts can be placed to increase yields without any risk of cereal crop lodging.

For many crop plants, diminished vegetative growth allows for denser planting and therefore higher yields relative to the soil surface. Another advantage of the smaller plants obtained by this method is that the crops are easier to grow and harvest.

Decreased growth of vegetative plants can also result in increased and improved yields, as nutrients and anabolic products are more beneficial to flower and fruit formation than to the vegetative portion of the plant.

Alternatively, growth regulators can also be used to promote vegetative growth. This has great benefits when harvesting plant parts. However, promotion of vegetative growth can also promote reproductive growth in which further anabolic products are formed, resulting in more or larger fruits.

In addition, beneficial effects on growth or yield include improved nutrient use efficiency, especially nitrogen (N) use efficiency, phosphorus (P) use efficiency, water use efficiency, transpiration, respiration and / or CO ₂ assimilation rate. It can be realized by good nodule engraftment, improvement of Ca metabolism and the like.

Similarly, growth regulators can be used to modify the composition of the plant, which in turn can result in improved quality of the harvested product. Parthenogenetic fruits may be formed under the influence of growth regulators. In addition, it can affect the gender of the flower. It is also possible to produce sterile pollen, which is very important in the breeding and production of hybrid seeds.

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

Under the influence of growth regulators, the amount of leaves relative to the plant can be controlled so that defoliation of the plant is achieved at the desired time. Such defoliation plays a major role in the mechanical harvesting of cotton, but is also of great interest for facilitating harvesting in other crops, such as viticulture. Plant defoliation can also be done to reduce transpiration of the plant prior to transplanting the plant.

In addition, growth regulators can modulate plant aging, which may increase the duration of green leaf area, prolong ripening period and improve yield quality.

Similarly, growth regulators can be used to regulate fruit dehiscence. On the other hand, it is possible to prevent premature fruit dehiscence. On the other hand, it is also possible to promote dehiscence of the fruit, or even flower picking (“flower picking”) to achieve the desired mass. In addition, growth modifiers can be used at the time of harvest to reduce the force required to cut the fruit, either to allow mechanical harvesting or to facilitate manual harvesting.

Growth regulators can also be used to achieve faster or otherwise delayed maturation of the harvested material before or after harvest. This is especially advantageous as it allows for optimal adjustment of market requirements. In addition, growth regulators can, in some cases, improve fruit color. In addition, growth regulators can also be used to synchronize maturation within a particular time period. This establishes the requirements for completing mechanical or manual harvesting in a single operation, for example for tobacco, tomato or coffee.

The use of growth regulators can further affect the rest of the seeds or buds of the plant, thus plants such as pineapples or ornamental plants in the nursery tend to germinate, germinate or bloom, for example. It germinates, buds or blooms at times not normally. In areas at risk of frost, it may be desirable to delay seed germination or germination with the help of growth regulators to avoid damage caused by late frost.

Finally, growth regulators can induce plant resistance to frost, drought or high salinity in the soil. This allows for plant cultivation in areas that are not normally appropriate for this purpose.

The compound of formula (I) also exhibits a strong enhancing effect in plants. Thus, compounds of formula (I) can be used to assemble plant defenses from unwanted microbial attack.

Plant-enhancing (resistance-inducing) substances in this context provide a plant defense system that allows treated plants to develop a high degree of resistance to these microorganisms when subsequently inoculated with unwanted microorganisms. It is a substance that can be stimulated.

Further, in the context of the present invention, the plant physiology effects of the present invention include: resistance to high or low temperatures, drought tolerance and recovery after drought stress, water use efficiency (related to reduced water consumption), flood tolerance. Includes abiotic stress resistance, including resistance to chemicals such as ozone stress and UV resistance, heavy metals, salts, pesticides, etc.

Biological stress resistance, including increased resistance to fungi, and increased resistance to nematodes, viruses and bacteria. In the context of the present invention, biological resistance preferably comprises increased resistance to fungi and to nematodes.

Plant health / plant quality and seed vitality, reduced grove defects, improved appearance, enhanced recovery after stress periods, improved pigmentation (eg, chlorophyll content, green maintenance effect, etc.) and photosynthetic efficiency Increased plant vitality, including improvements in.

In addition, the compounds of formula (I) can reduce the content of mycotoxins in the harvested material and the foods and feeds prepared from it. Mycotoxins are not particularly exclusive, but: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2- and HT2-toxin, fumonisin, zearalenone, moniliformin, fusalin, diaseotoxin. It contains ssilpenol (DAS), bubericin, enniatin, fusaloproliferin, fusalenol, ochratoxin, patulin, arsenic alkaloids and aflatoxins, which include, for example, the following fungi: F. F. acuminatum, F. F. Asiaticum, F. F. avenaceum, F. F. crokwellense, F. Krumorum, F.M. F. graminearum (Gibberella zeae), F. cerevisiae. Equiseti, F. Fujikoroy (F. fujikoroi), F. F. musum, F. F. oxysporum, F. oxysporum, F. oxysporum. F. proliferatum, F. F. poae, F. F. pseudograminearum, F. pseudograminearum, F. F. sambucinum, F. F. scirpi, F. F. semitectum, F. F. solani, F. F. sporotichoides, F. F. Langsetiae, F. F. subglutinans, F. subglutinans, F. F. tricinctum, F. tricinctum, F. By species of the genus Fusarium, such as F. verticillioides, and even A. Flabus, A. flavus. Parasiticus, A. Nomius, A. Ochraceus, A. A. clavatus, A. Terreus, A. Species of the genus Aspergillus, such as Aspergillus, P. versicolor. P. verrucosum, P. verrucosum. P. viridicatum, P. P. citrinum, P. citrinum, P. P. expansum, P. Claviforme, P. Species of the genus Penicillium, such as P. roqueforti, C.I. C. purpurea, C.I. C. fusiformis, C.I. C. paspari, C.I. It can be produced by species of the genus Clavicept, such as C. africana, species of the genus Stachybotry, and the like.

Compounds of formula (I) can also be used in the protection of materials to protect industrial materials against attack and destruction by phytopathogenic fungi.

In addition, the compounds of formula (I) can be used alone or in combination with other active ingredients as antifouling compositions.

Industrial material in this context is understood to mean inanimate material prepared for use in industry. For example, the industrial materials that will be protected from microbial modification or destruction by the compositions of the present invention are adhesives, glues, papers, wallpaper and cardboard / paperboard, textiles, carpets, leather, wood, fibers and thin fabrics. , Paints and plastic articles, cooling lubricants, and other materials that can be infected or destroyed by microorganisms. Mention that parts of manufacturing plants and structures that can be compromised by the growth of microorganisms, such as cooling water circulation channels, cooling and heating systems, as well as ventilation and air conditioning units, are within the range of materials to be protected. Can be done. Industrial materials within the scope of the invention preferably include adhesives, sizing agents, paper and thick paper, leather, wood, paints, cooling lubricants and heat conductive fluids, more preferably wood.

The compound of formula (I) can prevent adverse effects such as decay, putrefaction, discoloration, decolorization or mold formation.

When treating wood, the compounds of formula (I) can also be used against fungal diseases that tend to grow on or inside the lumber. The term "timber" means all types of wood species, and all types of such processed wood for construction, such as solid wood, high density wood, laminated wood and plywood. The method for treating timber according to the present invention is mainly in the step of contacting the composition according to the present invention. This includes, for example, direct application, spraying, soaking, infusion, or any other suitable means.

In addition, the compounds of formula (I) can be used to protect objects in contact with seawater or fresh seawater, especially hulls, shields, nets, structures, mooring rigging and signaling systems from deposits.

The compound of formula (I) can also be used to protect the storage. Storage is understood to mean natural substances of plant or animal origin or their processed products of natural origin for which long-term protection is desired.

Plant-derived stocks, such as stems, leaves, tubers, seeds, fruits, grains and other plant or plant parts, can be protected in a freshly harvested state or (preliminary) dried, humidified, ground. Can be protected after being processed by grinding, compression or roasting. Storage also includes both building timber, raw timber such as utility poles and fences, or timber in the form of finished products such as furniture. Animals of animal origin are, for example, leather, leather, fur and animal hair. The compositions of the present invention can prevent harmful effects such as decay, putrefaction, discoloration, decolorization or mold formation.

Microorganisms capable of degrading or denaturing industrial materials include, for example, bacteria, fungi, yeasts, algae and mucous organisms. The compounds of formula (I) are preferably against fungi, especially fungi, wood-discoloring fungi and wood-destroying fungi (ascomycetes, basidiomycetes, imperfecti and zygomycetes), as well as mucous organisms and algae. It works. Examples include microorganisms of the following genera: Alternaria (such as Alternaria tenuis); Aspergillus (such as Aspergillus niger); Genus Coniophora (Coniophora puetana, etc.); Genus Lentinus (Lentinus tigrininus, etc.); Etc.); Aureobasidium genus (Aureobasidium pullulans, etc.); Sclelohoma genus (Scleropoma pityophila, etc.); Trichoderma genus (Trichoderma viride), etc. , Seratocystis species, Fumicola species, Petriella species, Tricles species, Coriolus species, Groeofilrum species, Preurotus species, Polya species, Serpra species and Tyromiseus species Species, Cladosporium genus, Paesiromyces genus, Mucor genus, Escherichia coli, etc.; Pseudomonas aeruginosa, etc. Includes (such as Staphylococcus aureus), species of the genus Candida and species of the genus Saccharomyces (such as Saccharomyces cerevisae).

In addition, the compounds of formula (I) also have very good antifungal activity. They are, among other things, dermatophytosis and yeast, fungi and biphasic fungi (eg, species of the genus Candida such as Candida albicans, Candida glabratta), and Epidermophyton. Aspergillus sp., Aspergillus sp. It has a very broad antifungal activity spectrum against species of the genus Microsporon such as (Microsporon aspergillus). The enumeration of these fungi by no means constitutes a limitation of the included fungal spectrum, but merely an exemplary property.

The compound can also be used to control important fungal pathogens in fish and crustacean aquaculture, such as saprolegnia diclina in trout and saprolegnia parasitica in crayfish.

Therefore, the compound of formula (I) can be used for both medical and non-medical uses.

The compound of formula (I) can be used as it is, and may be in the form of a preparation thereof such as a ready-to-use solution, suspension, wettable powder, paste, soluble powder, powder and granule. It can be used in a usage form prepared from the form of the preparation. The application is carried out by a conventional method, for example, by watering, spraying, spraying, spraying over the entire surface, spraying, powder coating, foam formation, surface coating and the like. It is also possible to develop the active ingredient by the ultra-trace method or to inject the active ingredient preparation / active ingredient itself into the soil. It is also possible to process plant seeds.

Preferably, all plants and parts thereof according to the present invention are treated with wild plant species and plant cultivars, or those obtained by conventional biological breeding methods such as crosses or protoplast fusions, and even some thereof. It is possible to do. In a more preferred embodiment, where appropriate, transgenic plants and plant cultivars obtained by genetically engineered methods are treated in combination with conventional methods (genetically modified organisms) and portions thereof. The terms "part" or "part of plant" or "plant part" are described above. More preferably, commercially available or in-use plant cultivars of plants are treated according to the present invention. It is understood that plant cultivars have new traits (“traits”) and mean plants obtained by mutagenesis or recombinant DNA techniques by conventional breeding. They can be cultivars, varieties, biotypes or genotypes.

The treatment method according to the invention can be used for the treatment of genetically modified organisms (GMOs), such as plants or seeds. A genetically modified plant (or a transgenic plant) is a plant in which its non-homologous gene is stably integrated into the genome. The expression "non-homologous gene" is essentially a gene that is presented or constructed outside the plant and is introduced into the nuclear genome, chlorophyll genome, or mitochondrial genome. New or improved agriculture in transformed plants by expressing the protein or polypeptide of interest, or by down-regulating or silencing other genes (s) present in the plant. Means a gene that imparts a specific or different characteristic (eg, using antisense technology, co-suppression technology, RNA interference-RNAi-technology or microRNA-miRNA-technology). Non-homologous genes located within the genome are also referred to as transgenes. A transgene defined by its particular location within the plant genome is referred to as a transformation or transgenic event.

The plants and plant cultivars preferably treated according to the present invention, whether obtained by breeding and / or bioengineering means, have genetic material that imparts particularly advantageous and useful traits to these plants. Not included).

Plants and plant cultivars preferably similarly treated according to the present invention are resistant to one or more biological stresses. That is, the plant exhibits good protection against animals and harmful microorganisms such as nematodes, insects, ticks, phytopathogenic fungi, bacteria, viruses and / or viroids.

The plants and plant cultivars that can be similarly treated according to the present invention are plants that are resistant to one or more abiotic stresses. Abiotic stress conditions include, for example, drought, low temperature exposure, heat exposure, infiltration stress, flooding, increased salinity in soil, increased exposure to minerals, exposure to ozone, exposure to strong light, nitrogen. It can include restrictions on the use of nutrients, restrictions on the use of phosphorus nutrients, and shade repellent.

Plants and plant cultivars that can be similarly treated according to the present invention are plants characterized by the characteristic of increased yield. Increased yields in said plants include, for example, improved water use efficiency, water retention efficiency, improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, improved germination efficiency and accelerated maturation. It can be the result of physiology, growth and development. Yields are not limited to: early blooming, flowering control for hybrid seed production, seedling vitality, plant size, number and distance between nodes, root growth, seed size, fruit size, pod size, pods or ears. Further impact by improved plant structure, including number of pods, number of seeds per pod or ear, seed mass, increased seed ripening, reduced seed dispersal, pod dehiscence and reduced lodging resistance. Acceptable (stressed and non-stressed conditions). Additional yield traits include carbohydrate content and composition such as cotton or starch, protein content, oil content and composition, nutritional value, reduced anti-nutrient compounds, improved processability, and good storage stability. Seed composition is included.

The plants that can be treated according to the present invention generally result in higher yields, higher vitality, higher health, and higher resistance to biological and abiotic stress, heterosis, or heterosis. It is a hybrid plant that has already exhibited the characteristics of (hybrid vigor).

Plants or plant cultivated varieties that can be treated according to the present invention (obtained by plant biotechnology methods such as genetic engineering) are made resistant to herbicide-tolerant plants, i.e. one or more given herbicides. It is a plant. Such plants can be obtained by genetic transformation or by selecting plants containing mutations that confer such herbicide resistance.

Plants or plant cultivated varieties that can be treated according to the present invention (obtained by plant biotechnology methods such as genetic engineering) are made resistant to attack by insect resistant transgenic plants, i.e., certain target insects. It is a plant that is growing. Such plants can be obtained by genetic transformation or by selecting plants containing mutations that confer such insect resistance.

The plants or plant cultivated varieties that can be treated according to the present invention (obtained by plant biotechnology methods such as genetic engineering) are resistant to abiotic stress. Such plants can be obtained by genetic transformation or by selecting plants containing mutations that confer such stress tolerance.

Plants or plant cultivated varieties that can be treated according to the present invention (obtained by plant biotechnology methods such as genetic engineering) are subject to changes in the quantity, quality and / or storage stability of the harvested product, and / or harvested. Shows changes in the properties of certain components of the product.

The plants or plant cultivated varieties that can be treated according to the present invention (which can be obtained by plant biotechnology methods such as genetic engineering) are plants with alterations in fiber characteristics, such as cotton plants. Such plants can be obtained by genetic transformation or by selecting plants containing mutations that confer such alterations in fibrous characteristics.

The plants or plant cultivated varieties that can be treated according to the present invention (which can be obtained by plant biotechnology methods such as genetic engineering) are plants such as rapeseed plants or related Brassica plants with modifications of oil profile characteristics. be. Such plants can be obtained by genetic transformation or by selecting plants containing mutations that confer such alterations in oil profile properties.

The plants or plant cultivated varieties that can be treated according to the present invention (which can be obtained by plant biotechnology methods such as genetic engineering) are plants such as rapeseed plants or related Brassica plants that have seed shedding characteristics. Such plants can be obtained by genetic transformation or by selecting plants containing mutations that confer such alterations in seed threshing characteristics, rapeseed plants with delayed or reduced seed threshing. Including plants such as.

The plants or plant cultivated varieties that can be treated according to the present invention (which can be obtained by plant biotechnology methods such as genetic engineering) are plants such as tobacco plants that have a modification of the post-translation protein modification pattern.

Therefore, the compounds of the present invention are exemplified in Tables 1 and 2.

The table below exemplifies, but is not limited to, examples of compounds according to the invention. In the following examples, M + 1 (or M-1) will be observed by mass spectrometry, molecular ion peak plus or minus 1a, respectively. m. u. It means that it is (atomic mass unit). The'H-NMR data of the selected examples are described in the form of ¹ H-NMR peak list. For each signal peak, list the δ value in ppm and the number of protons in parentheses.

To calibrate the chemical shift with respect to the ¹ H spectrum, we use the chemical shift of the solvent used for tetramethylsilane and / or in particular for spectra measured in DMSO. Therefore, in the NMR peak list, a peak of tetramethylsilane may occur, but it is not always the case.

The ¹ H-NMR peak list is similar to a standard ¹ H-NMR print (print) and therefore includes all of the usually 15 peaks listed in the standard NMR interpretation.

Furthermore, those peaks may also indicate a standard 3 / 4-NMR print of the solvent, a stereoisomer of the compound of interest which is also the peak of the object and / or impurities of the invention.

Table 1 shows the compounds of the general formula (I).

^* Compound names were generated using Chemdraw Professional 16.0.

Table 2 shows the compounds of the general formula (Ia).

^* Compound names were generated using Chemdraw Professional 16.0.

The compounds of the invention defined by the general formula (I) and / or in Tables 1 and 2 can be prepared by known methods and by the various methods described in Schemes 1-2.

Scheme 1

The compound of formula 1a can be synthesized by treating compound 2 with trimethyl orthoformate in the presence of catalytic pTSA and then reacting with a _secondary amine of formula _HNR2R3 , as described in US20111020382.

Compound 1 is an important intermediate in which Y is a nitro group or a protected amine functional group, formula 3

（式中、Ｘはハロゲンであり、Ｙはニトロ基または保護アミン官能基である）の化合物を、Ｅｕｒｏｐｅａｎ Ｊｏｕｒｎａｌ ｏｆ Ｏｒｇａｎｉｃ Ｃｈｅｍｉｓｔｒｙ、２０１６（１０）、１９０８～１９１４頁；Ｇｒｅｅｎ Ｃｈｅｍｉｓｔｒｙ、２０１６、１６（７）、３４９４～３５００頁；およびＴｅｔｒａｈｅｄｒｏｎ Ｌｅｔｔｅｒｓ、２０１４、５５（３０）、４０９８～４１０１頁において言及されているように対応するアニリン誘導体と反応させることにより合成され得る。

(In the formula, X is a halogen and Y is a nitro group or a protected amine functional group), the compound of European Journal of Organic Chemistry, 2016 (10), pp. 1908-1914; Green Chemistry, 2016, 16 (7). ), pp. 3494-3500; and can be synthesized by reacting with the corresponding aniline derivative as referred to in Tetrahedron Letters, 2014, 55 (30), pp. 4098-4101.

Scheme 2

バックワルド条件（Buchwald Condition）

Buchwald Condition

The compounds of formula 1a are also J. Mol. Med. Seen in Chem 2012, Vol. 55, 19, 8538-48; Synlett 2012, Vol. 23, 13, 2504-10; and Journal of Organic Chemistry, 2010, Vol. 75, 19, 6477-88. As such, compound 4 can be synthesized by treatment with appropriately substituted aniline using Buchwald conditions.

The compounds of formula 4 can be synthesized by using the corresponding aniline derivatives and converting them to amidine using known literature methods.

The present invention is further exemplified in the following, but not limited to examples. The structure of the novel compound was confirmed by NMR and / or other suitable analysis as shown below.

Preparation of N'-[2,5-dimethyl-4- (phenylamino) phenyl] -N-ethyl-N-methylimideformamide Step A: 2,5-dimethyl-N-phenylbenzene-1,4-diamine 1 Tin (II) chloride (3.62 g) in a stirred solution of 4-anilino-2,5-dimethylnitrobenzene (1.3 g, 5.365 mmol) in 4-dioxane and concentrated HCl (1: 1) (30 ml). , 16.097 mmol) was added. The reaction mixture was heated at 100 ° C. for 3-4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and carefully based to pH 7-8 with sodium bicarbonate. The aqueous layer was extracted with 5% methanol / dichloromethane (3 x 100 ml). The combined organic layer was washed with water (1 x 100 ml) and brine solution (1 x 100 ml). The organic layer was dehydrated with anhydrous sodium sulfate. The organic layer is filtered and evaporated under high vacuum to give a residue, which is then purified by flash chromatography using 0-80% ethyl acetate: hexane as eluent to 2,5-dimethyl-. N-Phenylbenzene-1,4-diamine (0.9 g) was obtained as a solid. LCMS (M + H) 249.75

Step B: 4-aniline-2,5-dimethylaniline in N'-[2,5-dimethyl-4- (phenylamino) phenyl] -N-ethyl-N-methylimideformamide trimethyl orthoformate (80 ml) PTSA (0.02 g, 0.113 mmol) was added to a stirred solution of 0.8 g (3.791 mmol) and the reaction mixture was heated at 100 ° C. for 6 hours. After the amine had completely disappeared, the reaction mixture was cooled and the volatiles were evaporated. 1,4-Dioxane (20 ml) was added to the residue, followed by N-ethylmethylamine (0.45 g, 7.582 mmol). The reaction mixture was heated at 100 ° C. for 1-2 hours. After completion of the reaction, evaporation of the volatiles yields a residue, which is then purified by flash chromatography eluting with 0-60% ethyl acetate: hexane as eluent to N'-[2,5- Dimethyl-4- (phenylamino) phenyl] -N-ethyl-N-methylimideformamide (0.25 g) was obtained as a viscous substance. ^{1 1} H-NMR (400MHz, DMSO-d6) δ7.60 (bs, 1H), 7.17 (s, 1H), 7.08 (t, J = 7.8Hz, 2H), 6.88 (s, 1H), 6.64 (d, J = 7.3Hz, 3H), 6.60 (t, J = 7.3Hz, 1H), 3.51-3.35 (m, 2H), 3.02- 2.84 (bs, 3H), 2.10 (s, 3H), 2.07 (s, 3H), 1.12 (t, J = 7.1Hz, 3H)

Preparation of N'-{2,5-dimethyl-4- [methyl (phenyl) amino] phenyl} -N-ethyl-N-methylimideformamide Step A: Preparation of 4-N-methylanilino-2,5-dimethylaniline Tin (II) chloride (II) chloride (II) in a stirred solution of 4-N-methylaniline-2,5-dimethylnitrobenzene (2.0 g, 7.80 mmol) in 1,4-dioxane and concentrated HCl (1: 1) (50 ml). 3.62 g, 16.097 mmol) was added. The reaction mixture was heated at 100 ° C. for 3-4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and carefully based to pH 7-8 with sodium bicarbonate. The aqueous layer was extracted with 5% methanol / dichloromethane (3 x 100 ml). The combined organic layer was washed with water (1 x 100 ml) and brine solution (1 x 100 ml). The organic layer was dehydrated with anhydrous sodium sulfate. The organic layer is filtered and evaporated under high vacuum to give a residue, which is then purified by flash chromatography using 0-80% ethyl acetate: hexane as eluent to give 4-N-methylaniline. 2,5-Dimethylaniline (1.5 g) was obtained as a solid. LCMS (M + H) 227.40

Step B: Preparation of N'-{2,5-dimethyl-4- [methyl (phenyl) amino] phenyl} -N-ethyl-N-methylimideformamide 4-N-methylaniline in trimethyl orthoformate (80 ml) PTSA (0.02 g, 0.099 mmol) was added to a stirred solution of 2,5-dimethylaniline (0.7 g, 3.317 mmol). The reaction mixture was heated at 100 ° C. for 6 hours. After completion of the reaction, the reaction mixture was cooled and evaporated. 1,4-Dioxane was added to the residue, followed by N-ethylmethylamine (0.392 g, 6.635 mmol). The reaction mixture was heated at 100 ° C. for 2 hours. After the reaction was complete, the volatiles were evaporated. When the residue is purified by flash chromatography eluting with 0-60% ethyl acetate: hexane, N'-{2,5-dimethyl-4- [methyl (phenyl) amino] phenyl} -N-ethyl-N-methylimide Formamide (0.25) was obtained as a viscous substance. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.73-7.51 (bs, 1H), 7.09 (t, J = 8.0 Hz, 2H), 6.82 (s, 1H), 6. 69 (s, 1H), 6.61-6.54 (m, 1H), 6.42 (d, J = 7.8Hz, 2H), 3.49-3.34 (m, 2H), 3. 11 (s, 3H), 2.93 (s, 3H), 2.12 (s, 3H), 1.97 (s, 3H), 1.13 (t, J = 7.1Hz, 3H)

Preparation of N'-[2-Chloro-5-Methyl-4- (Phenylamino) Phenyl] -N-Ethyl-N-Methylimideformamide Step A: Preparation of 4-anilino-2-chloro-5-methylaniline Ethanol -4-Aniline-2-chloro-5-methylnitrobenzene (2 g, 7.61 mmol), iron (2.12 g, 3.80 mmol) and ammonium chloride (2.1 g,) in a water (1: 1.50 ml) mixture. The stirred solution (3.80 mmol) was heated at 9 ° C. for 2 hours. After the reaction was complete, the contents were passed through Celite and filtered. The filtrate was concentrated, diluted with ethyl acetate (300 ml) and then washed with saturated sodium bicarbonate solution. The organic layer was separated, dehydrated with anhydrous sodium sulfate and concentrated to give a crude compound, which was purified by flash column chromatography to give 4-anilino-2-chloro-5-methylaniline (1.6 g). Obtained as a viscous substance. LCMS (M + H) 233.74

Step B: Preparation of N'-[2-chloro-5-methyl-4- (phenylamino) phenyl] -N-ethyl-N-methylimideformamide 4-aniline-2-chloro in trimethyl orthoformate (80 ml) PTSA (0.02 g, 0.1137 mmol) was added to a stirred solution of -5-methylaniline (0.8 g, 3.791 mmol) and the reaction mixture was heated at 100 ° C. for 6 hours. After the reaction was complete, the reaction mixture was cooled and the volatiles were evaporated. 1,4-Dioxane was added to the residue, followed by N-ethylmethylamine (0.45 g, 0.65 ml, 7.582 mmol). The reaction mixture was heated at 100 ° C. for 2 hours. After the reaction was completed, the volatiles were evaporated under reduced pressure. Purification of the crude compound by flash chromatography eluting with 0-60% ethyl acetate: hexane reveals N'-[2-chloro-5-methyl-4- (phenylamino) phenyl] -N-ethyl-N-methylimide. Formamide (0.25 g) was obtained. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.76-7.56 (br, 1H), 7.32 (s, 1H), 7.14 (t, J = 7.8 Hz, 2H), 7. 06 (s, 1H), 6.85 (s, 1H), 6.72 (d, J = 8.2Hz, 2H), 6.68 (t, J = 7.3Hz, 1H), 3.42 ( m, 2H), 3.04-2.85 (br, 3H), 2.11 (s, 3H), 1.13 (t, J = 6.9Hz, 3H)

Preparation of N'-{2-Chloro-5-Methyl-4- [Methyl (Phenyl) Amino] Phenyl} -N-Ethyl-N-Methylimideformamide Step A: 5-Chloro-N-2-dimethyl-N- Preparation of Phenylbenzene-1,4-diamine 5-chloro-N, 2-dimethyl-4-nitro-N-phenylaniline (2 g, 7.24 mmol) in an ethanol-water (1: 1, 50 ml) mixture, iron A stirred solution of (2.02 g, 36.17 mmol) and ammonium chloride (1.93 g, 36.17 mmol) was heated at 90 ° C. for 2 hours. After the reaction was complete, the contents were filtered through Celite. The filtrate was concentrated, diluted with ethyl acetate (300 ml) and then washed with saturated sodium bicarbonate solution. The organic layer is separated, dehydrated with anhydrous sodium sulfate and concentrated to obtain a crude compound, which is purified by flash column chromatography to obtain 5-chloro-N-2-dimethyl-N-phenylbenzene-1,4. -Diamine (1.7 g) was obtained as a solid. LCMS (M + H) 227.32

Step B: Preparation of N'-{2-Chloro-5-Methyl-4- [Methyl (Phenyl) Amino] Phenyl} -N-Ethyl-N-Methylimideformamide 5-Chloro- in trimethyl (50 ml) orthoformate PTSA (0.02 g, 0.11 mmol) was added to a stirred solution of N-2-dimethyl-N-phenylbenzene-1,4-diamine (0.9 g, 3.6 mmol), and the reaction mixture was prepared at 100 ° C. It was heated for 6 hours. After the reaction was complete, the volatiles were evaporated. 1,4-Dioxane was added to the residue, followed by N-ethylmethylamine (0.45 g, 0.65 ml, 7.582 mmol). The reaction was heated at 100 ° C. for 2 hours. After the reaction is complete, the volatiles are evaporated and the residue is purified by flash chromatography eluting with 0-60% ethyl acetate: hexane to give N'-{2-chloro-5-methyl-4- [methyl (phenyl). ) Amino] phenyl} -N-ethyl-N-methylimideformamide (0.8 g) was obtained. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.79-7.63 (br, 1H), 7.13 (td, J = 7.0, 1.6 Hz, 2H), 7.08 (s, 1H) ), 6.97-6.88 (br, 1H), 6.64 (t, J = 7.1Hz, 1H), 6.46 (d, J = 7.7Hz, 2H), 3.51-3 .36 (m, 2H), 3.13 (s, 3H), 3.05-2.91 (br, 3H), 1.99 (s, 3H), 1.15 (t, J = 6.9Hz) , 3H)

Preparation of N- [4-([ethyl (methyl) amino] methylidene} amino) -2,5-dimethylphenyl] -N-phenylmethanesulfonamide Step A was performed as described in the above Examples.

Step B: Preparation of N- [4-([ethyl (methyl) amino] methylidene} amino) -2,5-dimethylphenyl] -N-phenylmethanesulfonamide (N- in trimethyl (20.00 ml) oltoformate) In a stirred solution of (4-amino-2,5-dimethylphenyl) -N-phenylmethanesulfonamide (0.5 g, 1.722 mmol), p-toluenesulfonic acid monohydrate (0.016 g, 0.086 mmol). ) Was added. The reaction mixture was stirred at 103 ° C. for 3 hours. After 3 hours, the volatile substance was evaporated and 1,4-dioxane (20 ml) was added to the residue under a nitrogen atmosphere. N-methylethaneamine. (1.018 g, 17.22 mmol) was added and stirred at 103 ° C. for 3 hours. After completion of the reaction, evaporation of the volatiles yielded a crude compound, which was then purified by flash column chromatography. The desired N'-(2,5-dimethyl-4- (N-phenylmethylsulfonamide) phenyl) -N-ethyl-N-methylformimideamide (0.294 g) was obtained ¹ H-NMR (. 400MHz, DMSO-d6) δ7.73-7.53 (br, 1H), 7.35 (m, 4H), 7.28 (s, 1H), 7.23-7.14 (m, 1H), 6.69 (s, 1H), 3.49-3.36 (bs, 1H), 3.32-3.28 (bs, 1H), 3.24 (s, 3H), 3.02-2. 87 (br, 3H), 2.19 (s, 3H), 2.16 (s, 3H), 1.12 (t, J = 7.1Hz, 3H)

Preparation of N''-{4-[(4-chlorophenyl) (methyl) amino] -2,5-dimethylphenyl} -N-ethyl-N-methylimideformamide Step A: N-1- (4-chlorophenyl) -Preparation of N'-1,2,5-trimethylbenzene-1,4-diamine N- (4-chlorophenyl) -N, 2,5-trimethyl-4 in ethanol (16 ml) and water (4.00 ml) -Ammonium chloride (0.442 g, 8.25 mmol) and iron (1.152 g, 20.64 mmol) were added to a solution of nitroaniline (0.6 g, 2.064 mmol). The reaction mixture was stirred at 65 ° C. for 2 hours. After completion of the reaction, the reaction was cooled to room temperature and filtered through Celite. Evaporation of the filtrate gave a residue, which was placed in water and extracted with ethyl acetate. The ethyl acetate layer was washed with water (2 x 100 ml) and brine solution (1 x 100 ml). The organic layer was collected and dehydrated with anhydrous sodium sulfate. The organic layer is filtered and evaporated to give a residue, which is purified by flash chromatography to give the desired N1- (4-chlorophenyl) -N1,2,5-trimethylbenzene-1,4-diamine (0. 5 g) was obtained. LCMS (M + H) 261.77

Step B: Preparation of N'-{4-[(4-chlorophenyl) (methyl) amino] -2,5-dimethylphenyl} -N-ethyl-N-methylimideformamide N- in trimethyl (20 ml) orthogeate P-Toluenesulfonic acid monohydrate (0) in a stirred solution of 1- (4-chlorophenyl) -N'-1,2,5-trimethylbenzene-1,4-diamine (0.5 g, 1.917 mmol) .036 g, 0.192 mmol) was added. The reactants were stirred at 105 ° C. for 3 hours. After the reaction was complete, the volatiles were evaporated. Dioxane (20.00 ml) was added to the residue, followed by N-methylethaneamine (1.133 g, 19.17 mmol) and the reaction mixture was stirred for 3 hours. After completion of the reaction, evaporation of the volatiles yields a crude product, which is purified by preparative HPLC to give the desired N'-(4-((4-chlorophenyl) (methyl) amino) -2, 5-Dimethylphenyl) -N-ethyl-N-methylformimideamide (0.35 g) was obtained. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.71-7.55 (br, 1H), 7.12 (dd, J = 7.1, 2.1 Hz, 2H), 6.83 (s, 1H) ), 6.70 (s, 1H), 6.40 (dd, J = 6.9, 2.3Hz, 2H), 3.48-3.34 (bs, 1H), 3.31-3.25 (Bs, 1H), 3.11 (s, 3H), 3.02-2.86 (br, 3H), 2.12 (s, 3H), 1.95 (s, 3H), 1.13 ( t, J = 7.1Hz, 3H).

Preparation of N'-{4-[(3-chlorophenyl) (methyl) amino] -2,5-dimethylphenyl} -N-ethyl-N-methylimideformamide Step A: N-1- (3-chlorophenyl)- Preparation of N'-1,2,5-trimethylbenzene-1,4-diamine N- (3-chlorophenyl) -N, 2,5-trimethyl-4- in ethanol (15 ml) and water (3.00 ml) Ammonium chloride (0.46 g, 8.6 mmol) and iron (0.960 g, 17.20 mmol) were added to a solution of nitroaniline (0.5 g, 1.720 mmol). The reaction mixture was stirred at 65 ° C. for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and filtered through Celite. Evaporation of the filtrate gave a residue, which was placed in water and extracted with ethyl acetate. The ethyl acetate layer is dehydrated with anhydrous sodium sulfate and evaporated to give a residue, which is purified by flash chromatography to obtain the desired N-1- (3-chlorophenyl) -N1,2,5-trimethylbenzene-1. , 4-Diamine (0.4 g) was obtained. LCMS (M + H) 262.77

Step B: Preparation of N''-{4-[(3-chlorophenyl) (methyl) amino] -2,5-dimethylphenyl} -N-ethyl-N-methylimideformamide N in trimethyl (16 ml) orthogeate P-Toluenesulfonic acid monohydrate (p-toluenesulfonic acid monohydrate) in a stirred solution of -1- (3-chlorophenyl) -N'-1,2,5-trimethylbenzene-1,4-diamine (0.4 g, 1.534 mmol). 0.029 g, 0.153 mmol) was added. The reaction mixture was stirred at 105 ° C. for 3 hours. After the reaction was complete, the volatiles were evaporated. Dioxane (16.00 ml) followed by N-methylethaneamine (0.907 g, 15.34 mmol) was added to the residue, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, evaporation of the volatiles yields a crude compound, which is then purified by flash column chromatography to give the desired N'-(4-((3-chlorophenyl) (methyl) amino) -2. , 5-Dimethylphenyl) -N-ethyl-N-methylformimideamide (0.23 g) was obtained. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.74-7.55 (br, 1H), 7.10 (t, J = 8.5 Hz, 1H), 6.84 (s, 1H), 6. 72 (s, 1H), 6.60 (dot, J = 7.3, 1.1Hz, 1H), 6.36 (m, 2H), 3.50-3.34 (m, 2H), 3. 12 (s, 3H), 3.03-2.87 (bs, 3H), 2.13 (s, 3H), 1.96 (s, 3H), 1.13 (t, J = 7.1Hz, 3H)

Preparation of N'-{4-[(3,4-dichlorophenyl) (methyl) amino] -2,5-dimethylphenyl} -N-ethyl-N-methylimideformamide Step A: N-1- (3,4) -Preparation of dichlorophenyl) -N-1,2,5-trimethylbenzene-1,4-diamine N- (3,4-dichlorophenyl) -N'-1, in ethanol (15 ml) and water (3.75 ml) Ammonium chloride (0.395 g, 7.38 mmol) and iron (1.030 g, 18.45 mmol) were added to a stirred solution of 2,5-trimethyl-4-nitroaniline (0.6 g, 1.845 mmol). .. The reaction was then stirred at 65 ° C. for 2 hours. After completion of the reaction, the reaction mixture was passed through Celite and filtered. Evaporation of the filtrate gave a residue, which was partitioned between ethyl acetate and water. The ethyl acetate layer is separated, dehydrated with anhydrous sodium sulfate and evaporated to give a residue, which is purified by flash chromatography to give the desired N-1- (3,4-dichlorophenyl) -N'-1, 2,5-trimethylbenzene-1,4-diamine (0.5 g) was obtained. LCMS (M + H) 296.31

Step B: Preparation of N'-{4-[(3,4-dichlorophenyl) (methyl) amino] -2,5-dimethylphenyl} -N-ethyl-N-methylimideformamide in trimethyl (20 ml) orthogeate A stirred solution of N-1- (3,4-dichlorophenyl) -N'-1,2,5-trimethylbenzene-1,4-diamine (0.5 g, 1.69 mmol) with p-toluenesulfonic acid monohydrate. Japanese product (0.016 g, 0.085 mmol) was added. Then, the reaction mixture was stirred at 105 ° C. for 3 hours. The volatile material was evaporated, then dioxane (20.00 ml) was added to the residue, followed by N-methylethaneamine (1.001 g, 16.94 mmol). The reaction mixture was stirred for 3 hours. After the reaction is complete, the volatiles are evaporated and the crude product is purified by column chromatography to give the desired N'-(4-((3,4-dichlorophenyl) (methyl) amino) -2,5-dimethyl). Phenyl) -N-ethyl-N-methylformimideamide (270 mg) was obtained. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.77-7.52 (br, 1H), 7.29 (d, J = 9.2 Hz, 1H), 6.85 (s, 1H), 6. 73 (s, 1H), 6.55 (d, J = 2.3Hz, 1H), 6.35 (dd, J = 9.2,2.3Hz, 1H), 3.52-3.35 (m) , 2H), 3.13 (s, 3H), 3.03-2.87 (bs, 3H), 2.12 (s, 3H), 1.96 (s, 3H), 1.13 (t, J = 6.9Hz, 3H)

Preparation of N'-{2-Chloro-5-Methyl-4- [Methyl (3,4,5-Trifluorophenyl) Amino] Phenyl} -N-Ethyl-N-Methylimideformamide Step A: 5-Chloro- N, 2-dimethyl-N- (3,4,5-trifluorophenyl) benzene-1,4-diamine 5-chloro-N, 2-dimethyl-4-nitro-N- (3) in an ethanol-water mixture , 4,5-Trifluorophenyl) Iron (0.895 g, 16.03 mmol) and ammonium chloride (0.857 g, 16.03 mmol) were added to a stirred solution of aniline (0.53 g, 1.603 mmol). The reaction mixture was heated at 90 ° C. for 2 hours. After completion of the reaction, the reaction mixture is filtered through Celite, concentrated and diluted with ethyl acetate (30 ml), washed with saturated sodium bicarbonate, the organic layer separated, dehydrated with anhydrous sodium sulfate and concentrated. A crude compound was obtained, which was purified by flash chromatography to give 5-chloro-N-1,2-dimethyl-N1- (3,4,5-trifluorophenyl) benzene-1,4-diamine (0. 35 g) was obtained as a light brown viscous substance. LCMS (M + H) 301.71

Step B: Preparation of N'-{2-chloro-5-methyl-4- [methyl (3,4,5-trifluorophenyl) amino] phenyl} -N-ethyl-N-methylimideformamide trimethyl oltostate ( Stirring 5-chloro-N-1,2-dimethyl-N'-1- (3,4,5-trifluorophenyl) benzene-1,4-diamine (0.3 g, 0.998 mmol) in 10 ml) A catalytic amount of p-toluenesulfonic acid monohydrate (0.019 g, 0.100 mmol) was added to the solution, and the reaction content was heated at 105 ° C. for 2 hours under a nitrogen atmosphere. After completion of the reaction, the volatiles are evaporated under high vacuum, the contents are diluted with 1,4-dioxane (8 ml) and N-ethylmethylamine (0.139 ml, 1.596 mmol) is gradually added at room temperature. Added. The contents were heated at 75 ° C. for 4 hours. After completion of the reaction, the dioxane was evaporated under high vacuum and purified by flash column chromatography using 35-90% ethyl acetate: hexane to give N'-(2-chloro-5-methyl-4- (methyl (2-chloro-5-methyl-4-). 3,4,5-Trifluorophenyl) amino) phenyl) -N-ethyl-N-methylformimideamide (0.299 g) was obtained as a viscous substance. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.83-7.64 (br, 1H), 7.14 (s, 1H), 7.00-6.92 (br, 1H), 6.20 ( dd, J = 12.0, 6.0Hz, 2H), 3.49-3.34 (m, 2H), 3.13 (s, 3H), 3.05-2.92 (br, 3H), 1.99 (s, 3H), 1.15 (t, J = 6.9Hz, 3H)

Preparation of N'-{2-Chloro-5-Methyl-4- [Methyl (3-Methylphenyl) Amino] Phenyl} -N-Ethyl-N-Methylimideformamide Step A: 5-Chloro-N, 2-dimethyl -N- (3-Methylphenyl) benzene-1,4-diamine 5-chloro-N, 2-dimethyl-4-nitro-N- (m-tolyl) aniline in an ethanol-water mixture (0.55 g, 1) A stirred solution of .892 mmol), iron (1.056 g, 18.92 mmol) and ammonium chloride (1.012 g, 18.92 mmol) was heated at 90 ° C. for 2 hours. After completion of the reaction, the reaction mixture is filtered through Celite, concentrated and diluted with ethyl acetate (30 ml), washed with saturated sodium bicarbonate, the organic layer separated, dehydrated with anhydrous sodium sulfate and concentrated. A residue was obtained, which was purified by flash column chromatography to give 5-chloro-N-1,2-dimethyl-N1- (m-tolyl) benzene-1,4-diamine (0.34 g) a light brown viscosity. Obtained as a substance. LCMS (M + H) 261.77

Step B: Preparation of N'-{2-Chloro-5-methyl-4- [methyl (3-methylphenyl) amino] phenyl} -N-ethyl-N-methylimideformamide 5 in trimethyl (10 ml) orthogeate A catalytic amount of p-toluenesulfonic acid in a stirred solution of -chloro-N-1,2-dimethyl-N-1- (m-tolyl) benzene-1,4-diamine (0.34 g, 1.304 mmol). A hydrate (0.025 g, 0.130 mmol) was added, and the reaction content was heated at 105 ° C. for 2 hours under a nitrogen atmosphere. After completion of the reaction, the volatiles were evaporated under vacuum, the residue was diluted with 1,4-dioxane (10 ml) and N-ethylmethylamine (0.181 ml, 2.086 mmol) was added slowly at room temperature. .. The contents were heated at 75 ° C. for 4 hours. After completion of the reaction, the dioxane was evaporated and the residue was purified by flash column chromatography using 35-90% ethyl acetate: hexane for N'-(2-chloro-5-methyl-4- (methyl (m-)). Trill) amino) phenyl) -N-ethyl-N-methylformimideamide (0.155 g) was obtained as a viscous substance. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.83-7.61 (br, 1H), 7.07 (s, 1H), 7.02 (t, J = 8.0 Hz, 1H), 6. 98-6.87 (br, 1H), 6.25 (dd, J = 8.0, 2.1Hz, 1H), 6.08-5.94 (m, 2H), 3.65 (s, 3H) ), 3.51-3.35 (m, 2H), 3.11 (s, 3H), 3.04-2.90 (br, 3H), 1.99 (s, 3H), 1.15 ( t, J = 6.9Hz, 3H)

Preparation of N'-{2-Chloro-4-[(3,4-dichlorophenyl) (methyl) amino] -5-methylphenyl} -N-ethyl-N-methylimideformamide Step A is described in the above Examples. I went like this.

Step B: Preparation of N'-{2-chloro-4-[(3,4-dichlorophenyl) (methyl) amino] -5-methylphenyl} -N-ethyl-N-methylimideformamide trimethyl oltodium acid (10 ml) In a stirred solution of 5-chloro-N-1- (3,4-dichlorophenyl) -N-1,2-dimethylbenzene-1,4-diamine (0.32 g, 1.014 mmol) in, a catalytic amount of p. -Toluenesulfonic acid monohydrate (0.019 g, 0.101 mmol) was added, and the reaction content was heated at 105 ° C. for 2 hours under a nitrogen atmosphere. After completion of the reaction, the contents were evaporated, the residue was diluted with 1,4-dioxane (10 ml) and N-ethylmethylamine (0.141 ml, 1.622 mmol) was added slowly at room temperature. The contents were heated at 75 ° C. for 4 hours. After completion of the reaction, the dioxane was evaporated and the residue was purified by flash column chromatography using 35-90% ethyl acetate: hexane to give N'-(2-chloro-4-((3,4-dichlorophenyl)) ( Methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide (0.302 g) was obtained as a viscous substance. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.83-7.64 (br, 1H), 7.32 (d, J = 9.2 Hz, 1H), 7.14 (s, 1H), 7. 02-6.89 (br, 1H), 6.60 (d, J = 2.7Hz, 1H), 6.36 (dd, J = 8.9, 3.0Hz, 1H), 3.50-3 .34 (m, 2H), 3.14 (s, 3H), 3.05-2.89 (br, 3H), 1.98 (s, 3H), 1.15 (t, J = 6.9Hz) , 3H)

N'-{2-Chloro-4-[(3-methoxyphenyl) (methyl) amino] -5-methylphenyl} -N-ethyl-N-methylimideformamide Step A is as described in the above Examples. gone.

Step B: Preparation of N'-{2-Chloro-4-[(3-methoxyphenyl) (methyl) amino] -5-methylphenyl} -N-ethyl-N-methylimideformamide in trimethyl (12 ml) orthogeate 5-Chloro-N-1- (3-methoxyphenyl) -N-1,2-dimethylbenzene-1,4-diamine (0.3 g, 1.084 mmol) in a stirred solution of p-toluene in a catalytic amount. Sulfonic acid monohydrate (0.021 g, 0.108 mmol) was added, and the reaction content was heated at 105 ° C. for 3 hours. After completion of the reaction, the volatile material was evaporated under high vacuum to give a residue, which was placed in 1,4-dioxane (12 ml). N-Ethylmethylamine (0.151 ml, 1.734 mmol) was added and the contents were heated at 75 ° C. for 4 hours. After completion of the reaction, the volatiles were evaporated and the residue was purified by flash column chromatography using 35-90% ethyl acetate: hexane to give N'-(2-chloro-4-((3-methoxyphenyl)). (Methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide (0.347 g) was obtained as a viscous substance. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.81-7.62 (br, 1H), 7.06 (s, 1H), 7.00 (t, J = 7.8 Hz, 1H), 6. 97-6.88 (br, 1H), 6.47 (d, J = 7.3Hz, 1H), 6.29 (s, 1H), 6.25 (dd, 8.0, 2.0Hz, 1H) ), 3.51-3.35 (m, 2H), 3.11 (s, 3H), 3.05-2.91 (br, 3H), 2.18 (s, 3H), 1.98 ( s, 3H), 1.15 (t, J = 7.1Hz, 3H)

N'-(2-Chloro-5-methyl-4- {methyl [4- (trifluoromethyl) phenyl] amino} phenyl) -N-ethyl-N-methylimideformamide Step A is described in the above Examples. I went like that.

Step B: Preparation of N'-(2-chloro-5-methyl-4- {methyl [4- (trifluoromethyl) phenyl] amino} phenyl) -N-ethyl-N-methylimideformamide trimethyl oltodium acid (10 ml) ) In a stirred solution of 5-chloro-N-1,2-dimethyl-N1- (4- (trifluoromethyl) phenyl) benzene-1,4-diamine (0.35 g, 1.112 mmol) in a catalytic amount. P-Toluenesulfonic acid monohydrate (0.021 g, 0.111 mmol) was added, and the reaction content was heated at 105 ° C. for 2 hours under a nitrogen atmosphere. After complete conversion of the starting material, the volatiles were evaporated and the residue was diluted with 1,4-dioxane (10 ml). N-Ethylmethylamine (0.155 ml, 1.779 mmol) was added slowly at room temperature. The contents were heated at 75 ° C. for 4 hours. After completion of the reaction, the dioxane was evaporated and the crude compound was purified by preparative HPLC to obtain N'-(2-chloro-5-methyl-4- (methyl (4- (trifluoromethyl) phenyl) amino) phenyl). -N-Ethyl-N-methylformimideamide (0.359 g) was obtained as a pale yellow viscous substance. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.83-7.66 (br, 1H), 7.45 (d, J = 8.7 Hz, 2H), 7.16 (s, 1H), 7. 03-6.92 (br, 1H), 6.55 (d, J = 8.7Hz, 2H), 3.51-3.35 (m, 2H), 3.20 (s, 3H), 3. 05-2.90 (br, 3H), 1.98 (s, 3H), 1.16 (t, J = 6.9Hz, 3H)

N'-{2-Chloro-5-Methyl-4- [Methyl (4-Methylphenyl) Amino] Phenyl} -N-Ethyl-N-Methylimideformamide Step A was performed as described in the above Examples. ..

Step B: Preparation of N'-{2-Chloro-5-Methyl-4- [methyl (4-methylphenyl) amino] phenyl} -N-ethyl-N-methylimideformamide 5 in trimethyl (10 ml) orthogeate -A catalytic amount of p-toluenesulfonic acid monohydration in a stirred solution of -chloro-N-1,2-dimethyl-N1- (p-tolyl) benzene-1,4-diamine (0.35 g, 1.342 mmol). A product (0.026 g, 0.134 mmol) was added, and the reaction content was heated at 105 ° C. for 2 hours under a nitrogen atmosphere. After completion of the reaction, the volatiles were evaporated under vacuum and the contents were diluted with 1,4-dioxane (10 ml). N-Ethylmethylamine (0.187 ml, 2.148 mmol) was added slowly at room temperature. The contents were heated at 75 ° C. for 4 hours. After completion of the reaction, the dioxane is evaporated to give a residue, which is purified by preparative HPLC to N'-(2-chloro-5-methyl-4- (methyl (p-tolyl) amino) phenyl)-. N-Ethyl-N-methylformimideamide (0.317 g) was obtained as a viscous substance. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.82-7.62 (br, 1H), 7.05 (s, 1H), 6.94 (m, 3H), 6.38 (dd, J = 11.4, 2.7Hz, 2H), 3.50-3.34 (m, 2H), 3.10 (s, 3H), 3.05-2.91 (br, 3H), 2.17 ( s, 3H), 1.98 (s, 3H), 1.15 (t, J = 6.9Hz, 3H)

N'-{2-Chloro-4-[(2-Methoxyphenyl) (methyl) amino] -5-methylphenyl} -N-ethyl-N-methylimideformamide Step A is as described in the above Examples. gone.

Step B: Preparation of N'-{2-Chloro-4-[(2-methoxyphenyl) (methyl) amino] -5-methylphenyl} -N-ethyl-N-methylimideformamide in trimethyl (10 ml) orthoformate 5-Chloro-N1- (2-methoxyphenyl) -N-1,2-dimethylbenzene-1,4-diamine (0.35 g, 1.265 mmol) in a stirring solution and a catalytic amount of p-toluenesulfonic acid. Monohydrate (0.024 g, 0.126 mmol) was added, and the reaction content was heated at 105 ° C. for 2 hours under a nitrogen atmosphere. After the reaction was complete, the volatiles were evaporated. The residue was diluted with 1,4-dioxane (10 ml). N-Ethylmethylamine (0.176 ml, 2.023 mmol) was added slowly at room temperature. The contents were heated at 75 ° C. for 4 hours. After completion of the reaction, the dioxane is evaporated under high vacuum and the residue is purified by preparative HPLC to give N'-(2-chloro-4-((2-methoxyphenyl) (methyl) amino) -5-methylphenyl). ) -N-Ethyl-N-methylformimideamide (0.310 g) was obtained as a viscous substance. ^{1 1} H-NMR (400MHz, DMSO-d6) δ7.76-7.56 (br, 1H), 7.03-6.89 (m, 3H), 6.81 (m, 1H), 6.79- 6.72 (br, 1H), 6.73-6.61 (m, 1H), 3.70 (s, 3H), 3.47-3.34 (2H), 3.01 (s, 3H) , 2.99-2.88 (br, 3H), 1.84 (s, 3H), 1.12 (t, J = 7.1Hz, 3H)

N- [5-Chloro-4- ({-[ethyl (methyl) amino] methylidene} amino) -2-methylphenyl] -N-phenylmethanesulfonamide Step A was performed as described in the above Examples. ..

Step B: Preparation of N- [5-chloro-4- ({-[ethyl (methyl) amino] methylidene} amino) -2-methylphenyl] -N-phenylmethanesulfonamide N in trimethyl (10 ml) orthogeate -(4-Amino-5-chloro-2-methylphenyl) -N-phenylmethanesulfonamide (0.32 g, 1.030 mmol) in a stirred solution with a catalytic amount of p-toluenesulfonic acid monohydrate (0). .020 g, 0.103 mmol) was added and the reaction contents were heated at 105 ° C. for 2 hours under a nitrogen atmosphere. After complete conversion of the amine derivative, the volatile material was evaporated under high vacuum to give a residue. 1,4-Dioxane (10 ml) was added to this residue, followed by N-ethylmethylamine (0.233 ml, 2.68 mmol) at room temperature. The contents were heated at 75 ° C. for 4 hours. After completion of the reaction, the dioxane was evaporated under high vacuum and the residue was purified by preparative HPLC to give -N'-(2-chloro-5-methyl-4- (N-phenylmethylsulfonamide) phenyl) -N. -Ethyl-N-methylformimideamide (0.07 g) was obtained as a viscous substance. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.81-7.65 (br, 1H), 7.61 (s, 1H), 7.43-7.33 (m, 4H), 7.23 ( td, J = 5.6, 2.9Hz, 1H), 6.95-6.87 (br, 1H), 3.54-3.34 (m, 2H), 3.27 (s, 3H), 3.03-2.91 (br, 3H), 2.20 (s, 3H), 1.14 (t, J = 6.9Hz, 3H)

N'-{2-Chloro-4-[(2-chlorophenyl) (methyl) amino] -5-methylphenyl} -N-ethyl-N-methylimideformamide Step A is performed as described in the above Examples. rice field.

Step B: Preparation of -N'-{2-chloro-4-[(2-chlorophenyl) (methyl) amino] -5-methylphenyl} -N-ethyl-N-methylimideformamide in trimethyl (10 ml) oltostate 5-Chloro-N1- (2-chlorophenyl) -N-1,2-dimethylbenzene-1,4-diamine (0.31 g, 1.102 mmol) in a stirred solution with a catalytic amount of p-toluenesulfonic acid. A hydrate (0.021 g, 0.110 mmol) was added, and the reaction content was heated at 105 ° C. for 2 hours under a nitrogen atmosphere. Volatiles were evaporated under high vacuum. The residue was diluted with 1,4-dioxane (10 ml). N-Ethylmethylamine (0.192 ml, 2.205 mmol) was added slowly at room temperature. The contents were heated at 75 ° C. for 4 hours. After completion of the reaction, the dioxane was evaporated under reduced pressure and the residue was purified by preparative HPLC to give -N'-(2-chloro-4-((2-chlorophenyl) (methyl) amino) -5-methylphenyl). -N-Ethyl-N-methylformimideamide (0.359 g) was obtained as a pale yellow viscous substance. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.80-7.59 (br, 1H), 7.40 (dd, J = 7.8, 1.4 Hz, 1H), 7.32-7.23 (M, 1H), 7.11-6.99 (m, 2H), 6.84 (s, 2H), 3.47-3.35 (m, 2H), 3.04 (s, 3H), 3.02-2.87 (br, 3H), 1.98 (s, 3H), 1.13 (t, J = 6.9Hz, 3H)

N'-{2-Chloro-4-[(4-chlorophenyl) (methyl) amino] -5-methylphenyl} -N-ethyl-N-methylimideformamide Step A is performed as described in the above Examples. rice field.

Step B: Preparation of N'-{2-chloro-4-[(4-chlorophenyl) (methyl) amino] -5-methylphenyl} -N-ethyl-N-methylimideformamide) in trimethyl (10 ml) orthogeate A catalytic amount of p-toluenesulfonic acid monohydrate in a stirred solution of 5-chloro-N1- (4-chlorophenyl) -N-1,2-dimethylbenzene-1,4-diamine (0.32 g, 1.138 mmol). A Japanese product (0.022 g, 0.114 mmol) was added, and the reaction content was heated at 105 ° C. for 2 hours under a nitrogen atmosphere. After complete conversion of the amine, the volatiles are removed under vacuum, the contents are diluted with 1,4-dioxane (10 ml) and N-ethylmethylamine (0.198 ml, 2.276 mmol) is gradually added at room temperature. Was added to. The contents were heated at 75 ° C. for 4 hours. After completion of the reaction, the dioxane was removed and the residue was purified by preparative HPLC to give -N'-(2-chloro-4-((4-chlorophenyl) (methyl) amino) -5-methylphenyl) -N- Ethyl-N-methylformimideamide (0.360 g) was obtained as a viscous substance. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.86-7.64 (br, 1H), 7.16 (dd, J = 6.9, 2.3 Hz, 2H), 7.11 (s, 1H) ), 7.01-6.90 (br, 1H), 6.44 (dd, J = 6.9, 2.3Hz, 2H), 3.51-3.34 (m, 2H), 3.13 (S, 3H), 3.04-2.92 (br, 3H), 1.98 (s, 3H), 1.15 (t, J = 6.9Hz, 3H)

N'-{2-Chloro-4-[(4-Methoxyphenyl) (methyl) amino] -5-methylphenyl} -N-ethyl-N-methylimideformamide Step A is as described in the above Examples. gone.

Step B: Preparation of N'-{2-chloro-4-[(4-methoxyphenyl) (methyl) amino] -5-methylphenyl} -N-ethyl-N-methylimideformamide in trimethyl (10 ml) orthoformate 5-Chloro-N1- (4-Methoxyphenyl) -N-1,2-dimethylbenzene-1,4-diamine (0.3 g, 1.084 mmol) in a stirring solution and a catalytic amount of p-toluenesulfonic acid. Monohydrate (0.021 g, 0.108 mmol) was added, and the reaction content was heated at 105 ° C. for 2 hours under a nitrogen atmosphere. After completion of the reaction, the volatile material was evaporated under high vacuum. The residue was diluted with 1,4-dioxane (10 ml). N-Ethylmethylamine (0.188 ml, 2.168 mmol) was added slowly at room temperature. The contents were heated at 75 ° C. for 4 hours and monitored by TLC. After completion of the reaction, the dioxane was evaporated and the residue was purified by preparative HPLC to obtain N'-(2-chloro-4-((4-methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-. Ethyl-N-methylformimideamide (0.079 g) was obtained as a viscous substance. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.82-7.62 (br, 1H), 7.03 (s, 1H), 6.96-6.85 (br, 1H), 6.77 ( dd, J = 6.9, 2.3Hz, 2H), 6.46 (dd, J = 6.9, 2.3Hz, 2H), 3.65 (s, 3H), 3.49-3.35 (M, 2H), 3.08 (s, 3H), 3.04-2.92 (br, 3H), 1.99 (s, 3H), 1.15 (t, J = 6.9Hz, 3H) )

N'-(2-Chloro-4-((4-Methoxy-3-methylphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide Step A is described in the above Examples. I went as described in.

Step B: Preparation of N'-(2-Chloro-4-((4-Methoxy-3-methylphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide Orthosilicic acid In a stirred solution of 5-chloro-N1- (4-methoxy-3-methylphenyl) -N-1,2-dimethylbenzene-1,4-diamine (0.3 g, 1.032 mmol) in trimethyl (10 ml) , A catalytic amount of p-toluenesulfonic acid monohydrate (0.196 g, 1.032 mmol) was added, and the reaction content was heated at 105 ° C. for 2 hours under a nitrogen atmosphere. After completion of the reaction, evaporation of the volatile material gave a residue, which was diluted with 1,4 dioxane (10 ml). N-Ethylmethylamine (0.090 ml, 1.032 mmol) was added slowly at room temperature. The contents were heated at 75 ° C. for 4 hours. After completion of the reaction, the dioxane was evaporated and the crude compound was purified by preparative HPLC to obtain N'-(2-chloro-4-((4-methoxy-3-methylphenyl) (methyl) amino) -5-methyl. Phenyl) -N-ethyl-N-methylformimideamide (0.124 g) was obtained as a viscous substance. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.91-7.57 (br, 1H), 7.03 (s, 1H), 6.98-6.83 (br, 1H), 6.75 ( d, J = 8.7Hz, 1H), 6.37 (d, J = 2.7Hz, 1H), 6.31 (dd, J = 8.7, 2.7Hz, 1H), 3.68 (s) , 3H), 3.51-3.37 (m, 2H), 3.07 (s, 3H), 3.05-2.90 (br, 3H), 2.05 (s, 3H), 1. 98 (s, 3H), 1.15 (t, J = 6.9Hz, 3H)

N'-(2-Chloro-4-((3,4-dimethoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide Step A is described in the above Examples. I went like this.

Step B: Preparation of N'-(2-Chloro-4-((3,4-dimethoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide trimethyl oltodium acid ( In a stirred solution of 5-chloro-N1- (3,4-methoxyphenyl) -N-1,2-dimethylbenzene-1,4-diamine (0.24 g, 0.782 mmol) in 10 ml), in a catalytic amount. p-Toluenesulfonic acid monohydrate (0.015 g, 0.078 mmol) was added, and the reaction contents were heated at 105 ° C. for 2 hours under a nitrogen atmosphere. After completion of the reaction, the volatile material was evaporated under vacuum. The residue was diluted with 1,4-dioxane (10 ml). N-Ethylmethylamine (0.122 ml, 1.408 mmol) was added slowly at room temperature. The contents were heated at 75 ° C. for 4 hours. After completion of the reaction, the dioxane was evaporated and the residue was purified by preparative HPLC to obtain N'-(2-chloro-4-((3,4-dimethoxyphenyl) (methyl) amino) -5-methylphenyl)-. N-ethyl-N-methylformimideamide (0.192 g) was obtained as a viscous substance. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.82-7.59 (br, 1H), 7.05 (s, 1H), 6.95-6.84 (br, 1H), 6.75 ( d, J = 8.7Hz, 1H), 6.19 (d, J = 2.7Hz, 1H), 5.95 (dd, J = 8.7, 2.7Hz, 1H), 3.64 (s) , 3H), 3.63 (s, 3H), 3.50-3.34 (br, 2H), 3.10 (s, 3H), 3.04-2.88 (br, 3H), 1. 99 (s, 3H), 1.14 (t, J = 6.9Hz, 3H)

N'-(2-Chloro-4-((3,5-dimethoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide Step A is described in the above Examples. I went like this.

Step B: Preparation of N'-(2-Chloro-4-((3,5-dimethoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide trimethyl oltostate ( 10 ml) in a stirred solution of 5-chloro-N1- (3,5-dimethoxyphenyl) -N-1,2-dimethylbenzene-1,4-diamine (0.28 g, 0.913 mmol) in a catalytic amount. p-Toluenesulfonic acid monohydrate (0.017 g, 0.091 mmol) was added, and the reaction contents were heated at 105 ° C. for 2 hours under a nitrogen atmosphere. After completion of the reaction, the volatile material was evaporated under vacuum. The residue was diluted with 1,4-dioxane (10 ml). N-Ethylmethylamine (0.143 ml, 1.643 mmol) was added slowly at room temperature. The contents were heated at 75 ° C. for 4 hours. After completion of the reaction, the dioxane was evaporated and purified by preparative HPLC to allow N'-(2-chloro-4-((3,5-dimethoxyphenyl) (methyl) amino) -5-methylphenyl) -N-. Ethyl-N-methylformimideamide (0.267 g) was obtained as a viscous substance. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.83-7.61 (br, 1H), 7.06 (s, 1H), 6.96-6.86 (1H), 5.87 (s, 1H), 5.58 (s, 2H), 3.63 (s, 6H), 3.51-3.34 (m, 2H), 3.10 (s, 3H), 3.04-2.87 (Br, 3H), 1.99 (s, 3H), 1.14 (t, J = 6.6Hz, 3H)

N-Ethyl-N'-(4-((3-methoxyphenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide Step A was performed as described in the above Examples.

Step B: Preparation of N-ethyl-N'-(4-((3-methoxyphenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide N1- (10 ml) in trimethyl oltostate In a stirred solution of 3-methoxyphenyl) -2,5-dimethylbenzene-1,4-diamine (0.22 g, 0.908 mmol), a catalytic amount of p-toluenesulfonic acid monohydrate (0.017 g, 0) .091 mmol) was added, and the reaction contents were heated at 105 ° C. for 2 hours under a nitrogen atmosphere. After completion of the reaction, the volatile material was evaporated under vacuum. The residue was diluted with 1,4-dioxane (10 ml). N-Ethylmethylamine (0.158 ml, 1.816 mmol) was added slowly at room temperature. The contents were heated at 90 ° C. for 4 hours. After completion of the reaction, the dioxane was evaporated and the crude compound was purified by preparative HPLC to obtain N-ethyl-N'-(4-((3-methoxyphenyl) amino) -2,5-dimethylphenyl) -N-. Methylformimide amide (0.235 g) was obtained as a viscous substance. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.70-7.49 (bs, 1H), 6.77 (s, 1H), 6.72 (d, J = 9.0 Hz, 2H), 6. 64 (s, 1H), 6.39 (d, J = 9.2Hz, 2H), 3.63 (s, 3H), 3.54-3.19 (bs, 2H), 3.05 (s, 3H), 2.91 (s, 3H), 2.09 (s, 3H), 1.96 (s, 3H), 1.11 (t, J = 7.1Hz, 3H)

N-Ethyl-N'-(4-((4-Methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide Step A is performed as described in the above Examples. rice field.

Step B: Preparation of N-ethyl-N'-(4-((4-methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide in trimethyl (10 ml) orthogeate A catalytic amount of p-toluenesulfonic acid was added to a stirred solution of N-1- (4-methoxyphenyl) -N-1,2,5-trimethylbenzene-1,4-diamine (0.31 g, 1.209 mmol). A hydrate (0.023 g, 0.121 mmol) was added, and the reaction content was heated at 105 ° C. for 2 hours under a nitrogen atmosphere. After completion of the reaction, the volatiles are evaporated under vacuum, the contents are diluted with 1,4-dioxane (10 ml) and N-ethylmethylamine (0.210 ml, 2.419 mmol) is added slowly at room temperature. bottom. The contents were heated at 90 ° C. for 4 hours. After completion, the dioxane was removed and the residue was purified by preparative HPLC using ammonium formate buffer to N-ethyl-N'-(4-((4-methoxyphenyl) (methyl) amino) -2,5. -Dimethylphenyl) -N-methylformimideamide (0.177 g) was obtained as a pale yellow viscous substance. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.70-7.49 (bs, 1H), 6.77 (s, 1H), 6.72 (d, J = 9.0 Hz, 2H), 6. 64 (s, 1H), 6.39 (d, J = 9.2Hz, 2H), 3.63 (s, 3H), 3.54-3.19 (bs, 2H), 3.05 (s, 3H), 2.91 (s, 3H), 2.09 (s, 3H), 1.96 (s, 3H), 1.11 (t, J = 7.1Hz, 3H)

N'-(2-Chloro-4-((2-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide Step A: N'-(4-bromo-2-chloro Preparation of -5-Methylphenyl) -N-Ethyl-N-Methylformimideamide A catalytic amount in a stirred solution of 4-bromo-2-chloro-5-methylaniline (2 g, 9.07 mmol) in trimethyl oltostate. The p-toluenesulfonic acid monohydrate (0.173 g, 0.907 mmol) was added, and the reaction content was heated at 105 ° C. for 2 hours under a nitrogen atmosphere. After the reaction is complete, the volatiles are removed under vacuum, the contents are diluted with 1,4-dioxane (15 ml) and N-ethylmethylamine (2.365 ml, 27.2 mmol) is added slowly at room temperature. bottom. The contents were heated at 90 ° C. for 4 hours. After completion of the reaction, dioxane was removed and purified by flash column chromatography using ethyl acetate: hexane as an eluent to purify N'-(4-bromo-2-chloro-5-methylphenyl) -N-ethyl-. N-Methylformimideamide (2.2 g) was obtained as a light brown viscous substance. LCMS (M + H) 289.60

Step B: N'-(2-chloro-4-((2-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide N'-(4-bromo- in toluene) 2-Chloro-5-methylphenyl) -N-ethyl-N-methylformimide amide (0.521 g, 1.800 mmol), 2-fluoroaniline (0.2 g, 1.800 mmol), BINAP (0.112 g, A stirred solution of 0.180 mmol) and cesium carbonate (1.290 g, 3.96 mmol) was degassed for 15 minutes, palladium (II) acetate (0.061 g, 0.090 mmol) was added and degassed for another 15 minutes. , The contents were heated at 110 ° C. for 8 hours. After completion of the reaction, the contents were filtered through Celite and purified by flash column chromatography to obtain N'-(2-chloro-4-((2-fluorophenyl) amino) -5-methylphenyl) -N. -Ethyl-N-methylformimideamide (0.1318 g) was obtained as a viscous substance. ^{1 1} H-NMR (400 MHz, chloroform-D) δ7.60-7.36 (br, 1H), 7.23 (s, 1H), 7.11-7.01 (m, 1H), 6.96 ( t, J = 7.6Hz, 1H), 6.73-6.85 (m, 3H), 5.38 (s, 1H), 3.68-3.22 (2H), 3.08 (s, 3H), 2.19 (s, 3H), 1.25 (t, J = 7.2Hz, 3H)

N'-(2-Chloro-4-((3-chlorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide Step A was performed as described in Examples.

Step B: N'-(2-chloro-4-((3-chlorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide 3-chloroaniline in toluene (1 g, 7. 84 mmol), N'-(4-bromo-2-chloro-5-methylphenyl) -N-ethyl-N-methylformimideamide (2.27 g, 7.84 mmol), BINAP (0.488 g, 0.784 mmol) ), A stirred solution of cesium carbonate (7.66 g, 23.52 mmol) was degassed for 15 minutes, palladium (II) acetate (0.264 g, 0.392 mmol) was added, and the contents were degassed for another 15 minutes. Was heated at 110 ° C. for 8 hours. After completion of the reaction, the contents were filtered through Celite and purified by flash column chromatography to obtain N'-(2-chloro-4-((3-chlorophenyl) amino) -5-methylphenyl) -N-. Ethyl-N-methylformimideamide (0.8 g) was obtained as a viscous substance. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.73 (bs, 1H), 7.66 (s, 1H), 7.10-7.14 (m, 1H), 7.07 (s, 1H) , 6.88 (s, 1H), 6.70-6.63 (m, 1H), 6.58-6.60 (m, 2H), 3.50-3.33 (2H), 3.04 -2.86 (3H), 2.08 (s, 3H), 1.13 (t, J = 7.0Hz, 3H)

N'-(2-Chloro-4-((3-chlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide Step A: N'-(2-chloro-4) -Preparation of ((3-chlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide (Compound 53) Compound 52 (0) from Example 26 in DMF at 0 ° C. Iodomethane (0.112 ml, 1.784 mmol) was added to a stirred solution of 0.3 g, 0.892 mmol) and sodium hydride (0.043 g, 1.784 mmol), and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was poured into crushed ice and diluted with ethyl acetate. The separated organic layer was washed with brine and dehydrated with anhydrous sodium sulfate. Evaporation under high vacuum gives a residue, which is purified by preparative HPLC to N'-(2-chloro-4-((3-chlorophenyl) (methyl) amino) -5-methylphenyl) -N. -Ethyl-N-methylformimideamide (0.249 g) was obtained as a pale yellow viscous substance. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.83-7.61 (1H), 7.10-7.14 (m, 2H), 6.95 (s, 1H), 6.63-6. 66 (m, 1H), 6.35-6.40 (m, 2H), 3.34-3.45 (m, 2H), 3.13 (s, 3H), 3.05-2.87 ( 3H), 1.97 (s, 3H), 1.14 (t, J = 6.9Hz, 3H)

N- (3-chlorophenyl) -N, 2,5-trimethyl-4-((morpholinomethylene) amino) aniline Step A was performed as described in Example 1.

Step B: Preparation of N- (3-chlorophenyl) -N, 2,5-trimethyl-4-((morpholinomethylene) amino) aniline N1- (3-chlorophenyl) -N-1,2, in trimethyl orthoformate A catalytic amount of p-toluenesulfonic acid monohydrate (0.010 g, 0.053 mmol) was added to a stirred solution of 5-trimethylbenzene-1,4-diamine (0.3 g, 1.150 mmol), and the reaction was carried out. The contents were heated at 105 ° C. for 2 hours in a nitrogen atmosphere. After the reaction was complete, the volatiles were removed under vacuum. The residue was diluted with 1,4-dioxane (10 ml) and morphine (0.200 ml, 2.301 mmol) was added slowly at room temperature. The contents were heated at 90 ° C. for 4 hours. After completion of the reaction, dioxane was removed and purified by preparative HPLC to dilute N- (3-chlorophenyl) -N, 2,5-trimethyl-4-((morpholinomethylene) amino) aniline (0.277 g). Obtained as a yellow viscous substance. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.69 (s, 1H), 7.07-7.11 (m, 1H), 6.85 (s, 1H), 6.75 (s, 1H) , 6.65-6.54 (1H), 6.34-6.36 (m, 2H), 3.61-3.63 (m, 4H), 3.59-3.38 (m, 4H) , 3.11 (s, 3H), 2.11 (s, 3H), 1.96 (s, 3H)

N- (3-chlorophenyl) -N, 2,5-trimethyl-4-((piperidine-1-ylmethylene) amino) aniline Step A was performed as described in Example 1.

Step B: N- (3-chlorophenyl) -N, 2,5-trimethyl-4-((piperidin-1-ylmethylene) amino) aniline N1- (3-chlorophenyl) -N-1,2 in trimethyl orthoformate , 5-trimethylbenzene-1,4-diamine (0.3 g, 1.150 mmol) was added with a catalytic amount of p-toluenesulfonic acid monohydrate (0.015 g, 0.079 mmol). The reaction contents were heated at 105 ° C. for 2 hours under a nitrogen atmosphere. After completion of the reaction, the volatiles were removed under vacuum, the contents were diluted with 1,4-dioxane (10 ml) and piperidine (0.228 ml, 2.301 mmol) was added slowly at room temperature. The contents were heated at 90 ° C. for 4 hours and monitored by TLC. Upon completion, dioxane was removed and purified by preparative HPLC using ammonium formate buffer to N- (3-chlorophenyl) -N, 2,5-trimethyl-4-((piperidine-1-ylmethylene) amino). Aniline (0.231 g) was obtained as an off-white viscous substance. ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.61 (s, 1H), 7.12-7.04 (m, 1H), 6.83 (s, 1H), 6.71 (s, 1H) , 6.58-6.60 (m, 1H), 6.34-6.36 (m, 2H), 3.64-3.33 (4H), 3.11 (s, 3H), 2.11. (S, 3H), 1.95 (s, 3H), 1.59-1.62 (m, 2H), 1.48-1.54 (m, 4H)

N'-(4-((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-cyanoformimideamide Step A was performed as described in Example 1.

Step B: N'-(4-((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-cyanoformimideamide N1- (3-chlorophenyl) -N- in trimethyl oltostate A catalytic amount of p-toluenesulfonic acid monohydrate (0.02 g, 0.105 mmol) was added to a stirred solution of 1,2,5-trimethylbenzene-1,4-diamine (0.3 g, 1.150 mmol). The reaction contents were added and heated at 105 ° C. for 2 hours under a nitrogen atmosphere. After completion of the reaction, the solvent was removed under vacuum and the contents were diluted with 1,4-dioxane (10 ml). Cyanamide (0.1 g, 2.379 mmol) was added slowly at room temperature. The contents were heated at 90 ° C. for 4 hours. After completion of the reaction, dioxane was removed and purified by preparative HPLC using ammonium formate buffer. N'-(4-((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl)- N-Cyanoformimide amide was obtained as an off-white solid (0.172 g). ^{1 1} H-NMR (400 MHz, DMSO-d6) δ11.09-10.13 (1H), 8.81-8.49 (1H), 7.38 (d, J = 41.7 Hz, 1H), 7. 10-7.14 (m, 1H), 7.05 (d, J = 13.8Hz, 1H), 6.66 (d, J = 7.3Hz, 1H), 6.46-6.39 (1H) ), 6.39-6.31 (1H), 3.14 (3H), 2.19 (3H), 2.01 (s 3H)

N-allyl-N'-(4-((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide Step A was performed as described in Example 1. ..

Step B: N-allyl-N'-(4-((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide N1- (3-chlorophenyl) in trimethyl oltoformate ) -N-1,2,5-trimethylbenzene-1,4-diamine (0.3 g, 1.150 mmol) in a stirred solution with a catalytic amount of p-toluenesulfonic acid monohydrate (0.02 g, 0). .105 mmol) was added and the reaction contents were heated at 105 ° C. for 2 hours under a nitrogen atmosphere. After completion of the reaction, the solvent was removed under vacuum, the contents were diluted with 1,4-dioxane (10 ml) and N-allylmethylamine (0.205 g, 2.88 mmol) was added slowly at room temperature. The contents were heated at 90 ° C. for 4 hours. After completion, the dioxane was removed and purified by preparative HPLC using ammonium formate buffer to obtain N-allyl-N'-(4-((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl). ) -N-Methylformimideamide was obtained as a light brown viscous substance (0.227 g). ^{1 1} H-NMR (400 MHz, DMSO-d6) δ7.69 (s, 1H), 7.07-7.11 (m, 1H), 6.84 (s, 1H), 6.72 (s, 1H) , 6.58-6.61 (m, 1H), 6.35 (t, J = 2.3Hz, 2H), 5.94-5.77 (1H), 5.18-5.23 (m, 2H), 4.13-3.78 (2H), 3.11 (s, 3H), 2.90 (bs, 3H), 2.11 (s, 3H), 1.96 (s, 3H).

As described herein, compounds of general formula (I) exhibit very high bactericidal activity exerted against a large number of phytopathogenic fungi that attack important crops. The activity of the compounds of the invention for one or more of the following was evaluated:

Biological test examples (in vitro test)
Example 1: Pyricularia oryzae (Imochi disease): The compound was dissolved in 0.3% DMSO and then added to potato dextrose agar medium just prior to dispensing into Petri dishes. 5 ml of medium containing the compound was dispensed into a 60 mm sterile Petriplate. After solidification, each plate was seeded with a 5 mm sized mycelium disc collected from the outer edge of the actively growing toxic culture plate. Plates were placed in a growing box at a temperature of 25 ° C. and 60% relative humidity for 7 days to measure hypertrophic growth. 300 ppm compound 1, 2, 3, 4, 5, 6, 7, 8, 9, 11, 13, 16, 18, 20, 24, 25, 26, 27, 28, 29, 30, 31, 33, 34 , 35, 36, 38, 39, 40, 42, 43, 44, 45, 46, 47, 48, 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, 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, 110, 111, 112, 113, 115, 116, 117, 118, 119, 121, 122, 123, 125, 126, 129, 130, 131, 133, 134, 135, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149,150,151,152,155,156,157,158,159,160,161,162,163,164,165,166,167,168,169,170,171,172,173,176,177, 178, 180, 181, 182, 184, 185, 186, 187, 188, 189, 190, 191, 192, 193, 194, 195, 196, 197, 198, 199, 200, 201, 202, 203, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 217, 218, 219, 220, 221, 222, 223, 224, 227, 228, 229 and 230 were found in these tests. It resulted in 70-100% control compared to untreated criteria showing the development of a wide range of diseases.

Example 2: Rhizoctonia solani (Rhizoctonia solani): Dissolve the compound in 0.3% DMSO and then immediately before dispensing into a Petri dish, potato dextrose agar medium. Added to. 5 ml of medium containing the compound was dispensed into a 60 mm sterile Petriplate. After solidification, each plate was seeded with a 5 mm sized mycelium disc collected from the outer edge of the actively growing toxic culture plate. Plates were placed in a growing box at a temperature of 25 ° C. and 60% relative humidity for 7 days to measure hypertrophic growth. In these tests, 300 ppm compounds 1, 2, 3, 4, 6, 7, 8, 9, 10, 11, 13, 14, 15, 16, 18, 19, 20, 21, 24, 25, 26, 27, 29, 30, 31, 33, 34, 35, 36, 38, 39, 40, 42, 43, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 70, 71, 72, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 135, 137, 139, 140, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 155, 156, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167,168,169,170,171,173,176,177,180,181,184,185,186,187,188,190,191,192,195,197,198,199,201,202,205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 219, 220, 221, 222, 228, 229 and 230 are 70% compared to untreated counterparts that have shown widespread disease outbreaks. It brought about 100% control.

Example 3: Botrytis cinerea (Botrytis cinerea): The compound was dissolved in 0.3% DMSO and then added to potato dextrose agar medium just prior to dispensing into Petri dishes. 5 ml of medium containing the compound was dispensed into a 60 mm sterile Petriplate. After solidification, each plate was seeded with a 5 mm sized mycelium disc collected from the outer edge of the actively growing toxic culture plate. Plates were placed in a growing box at a temperature of 22 ° C. and 90% relative humidity for 7 days to measure hypertrophic growth. In these tests, 300 ppm compounds 1, 2, 3, 4, 8, 9, 18, 19, 33, 34, 35, 38, 40, 46, 47, 48, 52, 53, 54, 55, 57, 58, 59, 60, 61, 62, 63, 64, 70, 72, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 86, 87, 88, 89, 93, 94, 95, 97, 98, 99, 100, 101, 103, 104, 105, 106, 107, 108, 110, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 129, 130, 133, 135, 142, 143, 144, 145, 146, 148, 149, 150, 151, 152, 153, 155, 156, 157, 158, 159, 160, 161, 162, 166, 167, 168, 169, 173, 177, 181, 186, 187, 197, 199, 206, 207, 209, 210, 211, 212, 213, 214, 217, 218, 219, 220, 221, 223, 225, 229 and 230 yielded 70-100% compared to untreated matching products that showed widespread disease outbreaks.

Example 4: Alternaria solani (Alternaria solani): Dissolve the compound in 0.3% DMSO and then add to potato dextrose agar medium just before dispensing into Petri dishes. rice field. 5 ml of medium containing the compound was dispensed into a 60 mm sterile Petriplate. After solidification, each plate was seeded with a 5 mm sized mycelium disc collected from the outer edge of the actively growing toxic culture plate. Plates were placed in a growing box at a temperature of 25 ° C. and 60% relative humidity for 7 days to measure hypertrophic growth. In these tests, 300 ppm compounds 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 15, 16, 18, 19, 20, 21, 22, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 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, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 110, 112, 115, 116, 117, 118, 119, 121, 123, 125, 126, 127, 128, 129, 130, 131, 132, 133, 135, 137, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 155, 156, 157, 158, 159, 160, 161, 163, 164, 165, 166, 167, 168, 169, 170, 171, 173, 176, 177, 180, 181, 184, 185, 186, 187, 188, 189, 190, 191, 192, 193, 195, 196, 197, 198, 199, 200, 201, 202, 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, and 230 provided 70-100% control compared to untreated counterparts that showed widespread disease outbreaks.

Example 5: Colletotrichum capsici (anthrax): Compounds were dissolved in 0.3% DMSO and then added to potato dextrose agar medium just prior to dispensing into Petri dishes. 5 ml of medium containing the compound was dispensed into a 60 mm sterile Petriplate. After solidification, each plate was seeded with a 5 mm sized mycelium disc collected from the outer edge of the actively growing toxic culture plate. Plates were placed in a growing box at a temperature of 25 ° C. and 60% relative humidity for 7 days to measure hypertrophic growth. In these tests, 300 ppm compounds 2, 3, 4, 7, 8, 9, 11, 15, 18, 19, 24, 25, 26, 27, 29, 31, 32, 33, 34, 35, 36, 38, 39, 40, 43, 44, 46, 48, 51, 52, 53, 54, 55, 57, 58, 59, 60, 61, 62, 63, 64, 66, 71, 72, 74, 75, 76, 77, 79, 80, 82, 83, 85, 86, 88, 89, 92, 93, 95, 96, 97, 98, 99, 100, 102, 104, 106, 110, 111, 112, 113, 116, 117, 118, 119, 121, 123, 125, 126, 127, 129, 131, 133, 135, 141, 142, 144, 145, 146, 147, 148, 149, 151, 152, 155, 156, 157, 158, 159, 160, 161, 162, 166, 167, 168, 169, 170, 171, 173, 176, 180, 181 202, 205, 206, 207, 209, 210, 211, 212, 213, 217, 218, 219, 220, 221, 222, 225 and 230 were compared to the untreated collated products that showed widespread disease outbreaks. It resulted in 70-100% control.

Example 6: Septoria lycopersici (tomato spot disease): The compound was dissolved in 0.3% DMSO and then added to potato dextrose agar medium just prior to dispensing into a Petri dish. 5 ml of medium containing the compound was dispensed into a 60 mm sterile Petriplate. After solidification, each plate was seeded with a 5 mm sized mycelium disc collected from the outer edge of the actively growing toxic culture plate. Plates were placed in a growing box at a temperature of 25 ° C. and 70% relative humidity for 7 days to measure hypertrophic growth. In these tests, 300 ppm compounds 1, 2, 3, 4, 6, 7, 8, 9, 11, 13, 15, 16, 18, 19, 20, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 43, 44, 45, 46, 47, 48, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 66, 72, 77, 86, 89, 98, 99, 102, 106, 110, 112, 116, 119, 123, 125, 126, 129, 135, 145, 148, 155, 166, 158, 159, 160, 161, 166, 167, 168, 169, 171, 173, 180, 184, 186, 188, 190, 191, 194, 195, 197, 198, 199, 202, 205, 206, 207, 208, 209, 211, 212, 213, 214, 217, 218, 219, 220, 221, 222, 223, 224, 225 and 230 are untreated collated products showing widespread disease outbreaks. Compared with, it brought about 80-1000% control.

Example 7: Fusarium culmorum (grain hem rot): The compound was dissolved in 0.3% DMSO and then added to potato dextrose agar medium just prior to dispensing into Petri dishes. 5 ml of medium containing the compound was dispensed into a 60 mm sterile Petriplate. After solidification, each plate was seeded with a 5 mm sized mycelium disc collected from the outer edge of the actively growing toxic culture plate. Plates were placed in a growing box at a temperature of 25 ° C. and 60% relative humidity for 7 days to measure hypertrophic growth. In these tests, 300 ppm compounds 1, 7, 8, 26, 27, 29, 31, 35, 38, 39, 40, 45, 52, 53, 54, 55, 57, 58, 59, 60, 61, 62, 64, 66, 71, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 89, 102, 104, 106, 116, 117, 119, 121, 123, 125, 126, 129, 145, 147, 148, 151, 153, 155, 156, 158, 159, 160, 161, 166, 168, 170, 172, 181, 197, 205, 206, 209, 210, 213, 220 and 221 provided 70-100% control compared to untreated collating products that showed widespread disease outbreaks.

Biological test example (greenhouse)
Example A: Pyricularia oryzae in rice
The compound was 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.

To test the preventive activity of the compound, healthy young rice seedlings / plants grown in a greenhouse were sprayed with a preparation of the active compound in a spray cabinet at the specified dosage using a hollow cone nozzle. One day after treatment, plants were inoculated with a spore suspension (sterile water) containing ^1.4x106 pyricularia oryzae inoculation material. The inoculated plant was then maintained at a temperature of 24 ° C. and a relative humidity of 95% in a green house chamber for disease manifestation.

The performance of the compounds was visually assessed by rating the treated plants 3, 7, 10 and 15 days after application on the severity of the disease (0-100% scale). The efficacy (% control) of the compound was calculated by comparing the disease grade in the treatment with the untreated subject. In addition, the sprayed plants were evaluated for the phytotoxic effects of the compounds by recording symptoms such as necrosis, bleaching and growth inhibition. 500 ppm of compounds 54, 58, 80, 129, 138 and 152 provided 70-100% control in these tests compared to untreated criteria showing the development of a wide range of diseases. None of these compounds showed any phytotoxicity to rice crops.

Example B: Test compound for Fusarium culmorum in wheat was 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.

To test the preventive activity of the compound, healthy young wheat plants grown in the greenhouse were sprayed with a preparation of the active compound in a spray cabinet at the specified dosage using a hollow cone nozzle. One day after treatment, plants were inoculated with a spore suspension (2% malt) containing ^2x106 fusarium-krumorum inoculum. The inoculated plants were then maintained in a greenhouse chamber at a temperature of 24 ° C. and 80-90% relative humidity for disease development.

Visual evaluation of compound performance was performed by grading the treated plants with disease severity (0-100% scale) on days 3, 7, 10 and 15 after application. The efficacy (% control) of the compound was calculated by comparing the disease grade in the treatment with the untreated subject. The sprayed plants were also evaluated for the phytotoxic effects of the compounds by recording symptoms such as necrosis, chlorosis and growth inhibition. In these tests, 500 ppm compounds 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 20, 21, 27, 28, 31, 35, 36, 82, 112, 139, 151, 152 and 158 resulted in 70-100% control compared to untreated counterparts that showed widespread disease outbreaks. None of these compounds showed any phytotoxicity to wheat crops.

Example H: Botrytis cinera test compound in tomato was 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.

To test the preventive activity of the compound, healthy young bean / chili plants grown in the greenhouse were sprayed with a preparation of the active compound in a spray cabinet at the specified dosage using a hollow cone nozzle. One day after treatment, plants were inoculated with a spore suspension (2% malt) containing ^1.2x106 Botrytis cinera inoculation material. The inoculated plant was then maintained at a temperature of 18-20 ° C. and a relative humidity of 90-100% in a green house chamber for disease manifestation.

Visual evaluation of compound performance was performed by grading the treated plants with disease severity (0-100% scale) on days 3, 7, 10 and 15 after application. The efficacy (% control) of the compound was calculated by comparing the disease grade in the treatment with the untreated subject. The sprayed plants were also evaluated for the phytotoxic effects of the compounds by recording symptoms such as necrosis, chlorosis and growth inhibition. In these tests, 500 ppm compounds 1, 2, 3, 4, 5, 6, 7, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 43, 44, 45, 46, 85, 86, 87, 88, 90, 96, 97, 99, 100, 102, 103, 123, 127, 128, 129, 133, 134, 135, 136, 137, 138, 150, 161, 162, 163 and 164 are compared with the untreated products. It resulted in 70-100% control. None of these compounds showed any phytotoxicity to tomato crops.

Example D: Alternaria solani test compound in tomato was 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.

To test the preventive activity of the compound, healthy young tomato plants grown in a greenhouse were sprayed with a preparation of the active compound in a spray cabinet at the specified dosage using a hollow cone nozzle. One day after treatment, plants were inoculated with a spore suspension (2% malt) containing 0.24x10 ⁶ Alternaria solani inoculum material. The inoculated plants were then maintained in a greenhouse chamber at a temperature of 22-24 ° C. and 90-95% relative humidity for disease development.

Visual evaluation of compound performance was performed by grading the treated plants with disease severity (0-100% scale) on days 3, 7, 10 and 15 after application. The efficacy (% control) of the compound was calculated by comparing the disease grade in the treatment with the untreated subject. The sprayed plants were also evaluated for the phytotoxic effects of the compounds by recording symptoms such as necrosis, chlorosis and growth inhibition. In these tests, 500 ppm compounds 1, 2, 3, 5, 6, 8, 12, 13, 14, 15, 16, 17, 18, 19, 20, 22, 23, 24, 25, 26, 28, 29, 30, 31, 32, 33, 35, 37, 40, 43, 44, 54, 66, 67, 75, 88, 89, 116, 117, 118, 119, 123, 124, 125, 129, 130, 131, 132, 139, 143, 148, 156, 157 and 158 provided 70-100% control compared to untreated products. None of these compounds showed any phytotoxicity to tomato crops.

Example E: Corynespora corrica test compound in tomatoes was 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.

To test the preventive activity of the compound, healthy young tomato plants grown in a green house were sprayed with the active compound preparation in a spray cabinet at a specified rate of application using a hollow cone nozzle. One day after treatment, plants were inoculated with a spore suspension (tween 20 aqueous solution) containing 2.6 × 10 ⁶ Corica spora corica inoculum materials. The inoculated plant was then maintained at a temperature of 22-24 ° C. and a relative humidity of 90-95% in a green house chamber for disease manifestation.

The performance of the compounds was visually assessed by rating the treated plants 3, 7, 10 and 15 days after application on the severity of the disease (0-100% scale). The efficacy (% control) of the compound was calculated by comparing the disease rating in the treatment with the untreated control. In addition, the sprayed plants were evaluated for the phytotoxic effects of the compounds by recording symptoms such as necrosis, bleaching and growth inhibition.

500 ppm of Compounds 1, 3, 13, 14, 15, 16, 17, 18, 19, 20 and 22 provided 70-100% control in these tests compared to untreated. None of these compounds showed any phytotoxicity to tomato crops.

Although the present invention has been described with reference to certain preferred embodiments, other embodiments will be apparent to those skilled in the art from the discussion herein. It will be apparent to those skilled in the art that neither the substance nor the method can make numerous modifications without departing from the scope of the invention.

<Appendix 1>
General formula (I)

During the ceremony
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 -Alkyne, C _1-12 -Haloalkyl, C _2-12 -Haloalkenyl, C _2-12 -Halo alkynyl, C _3-8 -Cycloalkyl, C _4-8 -Cycloalkenyl, C _5-8 -Selected from the group consisting of cycloalkynyls, in a cyclic ring system, one or more carbon atoms are N, O, and S (O). _n It may be replaced by a heteroatom selected from the group consisting of;
R ² And R ³ Independently, hydrogen, CN, S (O) _n R ″, OR ″, (C = O) -R ″, C _1-12 -Alkyl, C _2-12 -Alkenyl, C _2-12 -Alkyne, C _1-12 -Haloalkyl, C _2-12 -Haloalkenyl, C _2-12 -Halo alkynyl, C _3-8 -Cycloalkyl, C _4-8 -Cycloalkenyl, C _5-8 -Cycloalkynyl, C _5-18 -Aryl, C _7-19 -Aralkill, C _7-19 -Selected from the group consisting of alkaline reels; in a cyclic ring system, one or more carbon atoms are N, O, and S (O). _n It may be replaced by a heteroatom selected from the group consisting of;
R ¹ And R ² , R ² And R ³ Or R ¹ And R ³ With the atoms to which they are bonded, or with additional atoms selected from the group consisting of C, N, O, S, as well as C (= O), C (= S), S (O). _m And SiR' ₂ A 4- to 7-membered ring may be formed by optionally including 1 to 3 ring members selected from the group consisting of, and the ring may partially include one or more X, R',. OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR' ₂ May be replaced by; R ¹ , R ² And R ³ Are all based on X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR' ₂ It may be optionally replaced by one or more groups selected from the group consisting of;
R ⁴ , R ⁵ , R ⁶ And R ⁷ Independently, hydrogen, X, CN, SCN, SF ₅ , 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 -Alkyne, C _1-12 -Haloalkyl, C _2-12 -Haloalkenyl, C _2-12 -Halo alkynyl, 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 -Aralkill, C _7-19 -Selected from the group consisting of alkaline reels; in a cyclic ring system, one or more carbon atoms are N, O, and S (O). _n It may be replaced by a heteroatom selected from the group consisting of; all of the above groups are X, R', OR', SR', NR'. ₂ , SiR' ₃ , COOR', CN, and CONR' ₂ It may be optionally substituted by one or more groups selected from the group consisting of; or
R ⁴ And R ⁷ Or R ⁵ And R ⁶ With the atoms to which they are bonded, or with additional atoms selected from the group consisting of C, N, O, S, as well as C (= O), C (= S), S (O). _m And SiR' ₂ A 4- to 7-membered ring may be formed by optionally including 1 to 3 ring members selected from the group consisting of, and the ring may partially include one or more X, R',. OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR' ₂ May be replaced by; R ⁴ , R ⁵ , R ⁶ And R ⁷ Are all based on X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR' ₂ It may be optionally substituted by one or more groups selected from the group consisting of;
R ⁸ Is hydrogen, CN, SCN, S (O) _n R ″, SiR ″ ₃ , NR ″ R ″, (C = O) -R ″, CR ″ = NR ″, C _1-12 -Alkyl, C _2-12 -Alkenyl, C _2-12 -Alkyne, C _1-12 -Haloalkyl, C _2-12 -Haloalkenyl, C _2-12 -Halo alkynyl, C _3-8 -Cycloalkyl, C _4-8 -Cycloalkenyl, C _5-8 -Cycloalkynyl, C _5-18 -Aryl, C _7-19 -Aralkill, C _7-19 -Alkaline, heterocyclyl, C _3-8 -Selected from the group consisting of heterocyclylalkyl; in a cyclic ring system, one or more carbon atoms are N, O, and S (O). _n It may be replaced by a heteroatom selected from the group consisting of; all of the above groups are X, R', OR', SR', NR'. ₂ , SiR' ₃ , COOR', CN, and CONR' ₂ May be substituted with one or more groups selected from the group consisting of; or
A is condensed or non-condensed C _6-18 -Aryl, C _5-18 -Selected from the group consisting of heteroaryls, one or more carbon atoms are replaced by heteroatoms selected from N, O, S and also R ⁹ C (= O), C (= S), S (O) optionally substituted by one or more groups of _m And SiR' ₂ Includes 1 to 3 ring members selected from the group consisting of;
R ⁹ Is hydrogen, X, CN, SCN, SF ₅ , R ″, OR ″, NO ₂ , NR ″ ₂ , SiR' ₃ , (C = O) -R ″, S (O) _n R ″, OS (O) _n R ″, OSiR ″ ₃ , NR'S (O) _n R ″, 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 -Aral Kill, S (O) _n C _7-19 -Alka reel, C _1-12 -Alkyl, C _2-12 -Alkenyl, C _2-12 -Alkyne, C _1-12 -Haloalkyl, C _2-12 -Haloalkenyl, C _2-12 -Halo alkynyl, 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 -Aralkill, C _7-19 -Alkaline; Bicyclic C _5-12 -Alkyl, C _7-12 -Selected from the group consisting of alkenyl; in a cyclic ring system, one or more carbon atoms are N, O, and S (O). _n It may be replaced by a heteroatom selected from the group consisting of; all of the above groups are X, R', OR', SR', NR'. ₂ , SiR' ₃ , COOR', CN, and CONR' ₂ It may be substituted with one or more groups selected from the group consisting of; or two Rs. ⁹ With the atoms to which they are bonded, or with additional atoms selected from the group consisting of C, N, O, S, as well as C (= O), C (= S), S (O). _m And SiR' ₂ A 4- to 10-membered ring may be formed by optionally including 1 to 3 ring members selected from the group consisting of, and the ring may partially include one or more X, R',. OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR' ₂ May be replaced by;
R ⁸ And R ⁹ Are all based on X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR' ₂ It may be optionally substituted by one or more groups selected from the group consisting of;
X represents halogen;
R'is a linear or branched chain C optionally substituted with hydrogen, one or more Xs. _1-12- Alkyl or cyclic C _3-10 -Represents alkyl;
R ″ is hydrogen; NR ″ ₂ , OR', straight chain or branched chain C _1-12 -Alkyl, C _1-12 -Haloalkyl, cyclic C _3-8 -Alkyl, X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR' ₂ Optionally substituted by one or more groups selected from the group consisting of C, optionally substituted by one or more R' _5-18 -Represents aryl;
m and n represent integers, n = 0, 1 or 2; m = 1 or 2) compound,
And agriculturally acceptable salts, metal complexes, isomers / structural isomers, stereoisomers, diastereomers, enantiomers, tautomers, or N-oxides of said compounds.

<Appendix 2>
Each substituent is independently selected from the following:
R ¹ But hydrogen, C _1-6 -Alkyl, C _1-6 -Alkoxy, C _1-6- Alkylthio, C _1-6 -Haloalkyl, C _3-8 -Cycloalkyl;
R ² And R ³ But C _1-6 -Alkyl, C _2-6 -Alkenyl, C _2-6 -Alkyne, C _1-6 -Alkoxy, C _1-6- Alkylthio, C _1-6 -Haloalkyl, C _3-8 -Cycloalkyl;
R ¹ And R ² , R ² And R ³ Or R ¹ And R ³ With the atoms to which they are bonded, or with additional atoms selected from the group consisting of C, N, O, S, as well as C (= O), C (= S), S (O). _m And SiR' ₂ A 4- to 7-membered ring may be formed by optionally including 1 to 3 ring members selected from the group consisting of, and the ring may partially include one or more X, R',. OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR' ₂ May be replaced by;
R ⁴ And R ⁵ But X, CN, S (O) _n R ″, NR ″ R ″, (C = O) -R ″, CR ″ = NR ″, C _1-6 -Alkyl, C _2-6 -Alkenyl, C _2-6 -Alkyne, C _1-6 -Haloalkyl, C _1-6 -Haloalkylthio, C _3-8 -Cycloalkyl, C _3-8 -Cycloalkylthio;
R ⁶ And R ⁷ However, hydrogen, X, CN, S (O) _n R ″, NR ″ R ″, (C = O) -R ″, CR ″ = NR ″, C _1-6 -Alkyl, C _2-6 -Alkenyl, C _2-6 -Alkyne, C _1-6 -Haloalkyl, C _1-6 -Haloalkylthio, C _3-8 -Cycloalkyl, C _3-8 -Cycloalkylthio;
R ⁴ And R ⁷ Or R ⁵ And R ⁶ With the atoms to which they are bonded, or with additional atoms selected from the group consisting of C, N, O, S, as well as C (= O), C (= S), S (O). _m And SiR' ₂ A 4- to 7-membered ring may be formed by optionally including 1 to 3 ring members selected from the group consisting of, and the ring may partially include one or more X, R',. OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR' ₂ May be replaced by;
R ⁸ But hydrogen, CN, S (O) _n R ″, NR ″ R ″, (C = O) -R ″, CR ″ = NR ″, C _1-6 -Alkyl, C _2-6 -Alkenyl, C _2-6 -Alkyne, C _1-6 -Haloalkyl, C _3-8 -Cycloalkyl, C _3-8 -Heterocyclyl, C _3-8 -Heterocyclylalkyl;
R ⁹ But X, CN, SCN, SF ₅ , R ″, OR ″, NO ₂ , NR ″ ₂ , SiR' ₃ , (C = O) -R ″, S (O) _n R ″, OS (O) _n R ″, OSiR ″ ₃ , NR'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 -Alkyne, 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 or two Rs ⁹ With the atoms to which they are bonded, or with additional atoms selected from the group consisting of C, N, O, S, as well as C (= O), C (= S), S (O). _m And SiR' ₂ A 4- to 10-membered ring may be formed by optionally including 1 to 3 ring members selected from the group consisting of, and the ring may partially include one or more X, R',. OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR' ₂ May be replaced by;
A is one or more R ⁹ Phenyl, naphthalenyl, frills, thienyl, pyrrolyl, isooxazolyl, isothiazolyl, pyrazolyl, oxazolyl, imidazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridadinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, benzoimidazolyl Benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinazolinyl, cinnonyl;
R ¹ ~ R ⁹ However, X, R ", OR", SR ", NR" ₂ , SiR' ₃ , COOR', CN, and CONR' ₂ The compound of the general formula (I) according to Appendix 1, which may be further optionally substituted with one or more groups selected from the group consisting of.
And an agriculturally acceptable salt, isomer / structural isomer, stereoisomer, diastereoisomer, enantiomer, tautomer, or N-oxide of the compound.

<Appendix 3>
Each substituent is independently selected from the following:
R ¹ But hydrogen or C _1-6 -Alkyl;
R ² And R ³ But C _1-6 -Alkyl, C _1-6 -Haloalkyl;
R ⁴ And R ⁵ But X, CN, C _1-6 -Alkyl, C _1-6 -Haloalkyl, C _3-8 -Cycloalkyl;
R ⁶ And R ⁷ But hydrogen, X, C _1-6 -Alkyl, C _1-6 -Haloalkyl;
R ⁸ But hydrogen, CN, S (O) _n R ″, (C = O) -R ″, C _1-6 -Alkyl, C _1-6 -Haloalkyl, C _2-6 -Alkenyl, C _2-6 -Alkyne, C _3-8 -Cycloalkyl, C _3-6 -Heterocyclyl, C _3-6 -Heterocyclylalkyl;
R ⁹ But X, CN, SCN, SF ₅ , R ″, OR ″, NO ₂ , NR ″ ₂ , SiR' ₃ , (C = O) -R ″, S (O) _n R ″, C _1-6 -Alkyl-S (O) _n R ″, OS (O) _n R ″, OSiR ″ ₃ , NR'S (O) _n R ″, C _1-6 -Alkyl- (C = O) -R ", CR" = NR ", SC _1-6 -Alkyl, C _2-6 -Alkenyl, C _2-6 -Alkyne, 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 or two Rs ⁹ With the atoms to which they are bonded, or with additional atoms selected from the group consisting of C, N, O, S, as well as C (= O), C (= S), S (O) m and SiR. ' ₂ A 4- to 10-membered ring may be formed by optionally including 1 to 3 ring members selected from the group consisting of, and the ring may partially include one or more X, R',. OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and CONR' ₂ May be replaced by;
A is one or more R ⁹ Phenyl, naphthalenyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, oxazolyl isoxazolyl, oxadiazolyl, pyridinyl, pyridadinyl, pyrimidinyl, pyrazinyl and quinolinyl substituted with.
R ¹ ~ R ⁹ However, X, R ", OR", SR ", NR" ₂ , SiR' ₃ , COOR', CN, and CONR' ₂ The compound of the general formula (I) according to Appendix 1, 2 or 4, which may be further optionally substituted with one or more groups selected from the group consisting of.
And an agriculturally acceptable salt, isomer / structural isomer, stereoisomer, diastereoisomer, enantiomer, tautomer, or N-oxide of the compound.

<Appendix 4>
The compound of the general formula (I) is
(Serial number 1) N'-(2,5-dimethyl-4- (phenylamino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 2) N'-(2,5-dimethyl-4- (methyl (phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 3) N'-(2-chloro-5-methyl-4- (phenylamino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 4) N'-(2-chloro-5-methyl-4- (methyl (phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 5) N'-(2,5-dimethyl-4- (N-phenylmethylsulfonamide) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 6) N'-(2,5-dimethyl-4- (methyl (2-methyl-4- (perfluoropropane-2-yl) phenyl) amino) phenyl) -N-ethyl-N-methylformimide amide ;
(Serial number 7) N'-(4-((4-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 8) N'-(4-((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 9) N'-(4-((3,4-dichlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 10) N'-(2-chloro-5-methyl-4- (methyl (3,4,5-trifluorophenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 11) N'-(2-chloro-5-methyl-4- (methyl (m-tolyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 12) N'-(2-chloro-4-((3,4-dichlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 13) N'-(2-chloro-4-((3-methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 14) N'-(2-chloro-5-methyl-4- (methyl (4- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 15) N'-(2-chloro-5-methyl-4- (methyl (p-tolyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 16) N'-(2-chloro-4-((2-methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 17) N'-(2-chloro-5-methyl-4- (N-phenylmethylsulfonamide) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 18) N'-(2-chloro-4-((2-chlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 19) N'-(2-chloro-4-((4-chlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 20) N'-(2-chloro-4-((4-methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 21) N'-(2-chloro-4-((4-methoxy-3-methylphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 22) N'-(2-chloro-4-((3,4-dimethoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 23) N'-(2-chloro-4-((3,5-dimethoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 24) N'-(2,5-dimethyl-4- (methyl (m-tolyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 25) N-ethyl-N'-(4-((3-methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 26) N'-(2,5-dimethyl-4- (methyl (p-tolyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 27) N-ethyl-N'-(4-((4-methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 28) N-ethyl-N'-(4-((3-methoxyphenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 29) N'-(2,5-dimethyl-4- (m-tolylamino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 30) N'-(2,5-dimethyl-4- (p-tolylamino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 31) N'-(4-((4- (tert-butyl) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 32) N'-(4-((4- (tert-butyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 33) N'-(4-((2-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 34) N'-(2-chloro-4-((2-chlorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 35) N-ethyl-N'-(4-((2-fluorophenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 36) N-ethyl-N'-(4-((2-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 37) N'-(2-chloro-4-((2-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 38) N-ethyl-N'-(4-((3-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 39) N-ethyl-N'-(4-((4-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 40) N'-(4-((2-chlorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 41) N- (4-(((ethyl (methyl) amino) methylene) amino) -2,5-dimethylphenyl) -N-phenylacetamide;
(Serial number 42) N'-(2-chloro-5-methyl-4- (methyl (pyridine-2-yl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 43) N'-(4-((4-chlorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 44) N-ethyl-N'-(4-((4-fluorophenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 45) N-ethyl-N'-(4-((2-methoxyphenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 46) N-ethyl-N'-(4-((3-fluorophenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 47) N'-(2-chloro-4-((2-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 48) N'-(2-chloro-4-((3-chlorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 49) N- (3-chlorophenyl) -N, 2,5-trimethyl-4-((morpholinomethylene) amino) aniline;
(Serial number 50) N'-(2-chloro-4-((3-chlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 51) N- (3-chlorophenyl) -N, 2,5-trimethyl-4-((piperidine-1-ylmethylene) amino) aniline;
(Serial number 52) N-allyl-N'-(4-((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 53) N'-(4-((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-isopropyl-N-methylformimideamide;
(Serial number 54) N'-(4-((2-bromophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 55) N'-(4-((3-chlorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 56) N-ethyl-N'-(4-((4-methoxyphenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 57) N'-(2,5-dimethyl-4-((2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 58) N'-(2,5-dimethyl-4- (methyl (2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 59) N'-(2,5-dimethyl-4-((4- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 60) N'-(2,5-dimethyl-4-((3- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 61) N'-(2,5-dimethyl-4- (methyl (4- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 62) N'-(2,5-dimethyl-4- (methyl (3- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 63) N'-(2,5-dimethyl-4-((3- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 64) N'-(4-((2-bromophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 65) N-ethyl-N'-(4-((2-methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 66) N'-(2,5-dimethyl-4- (methyl (3- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 67) N'-(2-chloro-5-methyl-4-((3- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 68) N'-(2-chloro-5-methyl-4- (m-tolylamino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 69) N'-(2-chloro-4-((3-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 70) N'-(2-chloro-5-methyl-4- (o-tolylamino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 71) N'-(2-chloro-4-((4-chlorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 72) N'-(2,5-dimethyl-4- (o-tolylamino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 73) N'-(2-chloro-4-((4-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 74) N'-(2-chloro-5-methyl-4- (methyl (o-tolyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 75) N'-(4-((2-bromophenyl) amino) -2-chloro-5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 76) N'-(4-((2-bromophenyl) (methyl) amino) -2-chloro-5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 77) N'-(2,5-dimethyl-4- (methyl (o-tolyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 78) N'-(2-chloro-4-((2-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 79) N'-(2-chloro-5-methyl-4-((2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 80) N'-(2-chloro-5-methyl-4- (methyl (2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 81) N'-(2-chloro-5-methyl-4-((4- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 82) N'-(2-chloro-4-((3-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 83) N'-(2-chloro-4-((4-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 84) N'-(2-chloro-4-((3-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 85) N'-(2-chloro-4-((4-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 86) N'-(2,5-dimethyl-4-((3- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 87) N'-(2-chloro-5-methyl-4-((3- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 88) N'-(2-chloro-5-methyl-4- (methyl (3- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 89) N'-(2,5-dimethyl-4- (methyl (3- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 90) N'-(4-((2,6-difluorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 91) N'-(2-chloro-4-((2,6-difluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 92) N'-(4-((2,6-difluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 93) N'-(2-chloro-4-((2,6-difluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 94) N'-(4-((2-chloro-6-fluorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 95) N'-(2-chloro-4-((2-chloro-6-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 96) N'-(4-((2-chloro-6-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 97) N'-(2,5-dimethyl-4-((4- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 98) N'-(4-((2,6-dichloro-4- (trifluoromethyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 99) N'-(2,5-dimethyl-4-((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 100) N'-(2-chloro-5-methyl-4-((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 101) N'-(2-chloro-5-methyl-4-((3- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 102) N'-(2,5-dimethyl-4-((4- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 103) N'-(2-chloro-5-methyl-4-((4- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 104) N'-(2,5-dimethyl-4- (methyl (2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 105) N'-(2-chloro-5-methyl-4- (methyl (2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 106) N'-(2,5-dimethyl-4- (methyl (4- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 107) N'-(2-chloro-5-methyl-4- (methyl (4- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 108) N'-(2-chloro-5-methyl-4- (methyl (3- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 109) N'-(2-Chloro-5-methyl-4- (N-phenylethyl sulfonamide) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 110) N'-(2-chloro-4-((2,4-dichloro-6- (trifluoromethyl) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide ;
(Serial number 111) N'-(2-chloro-5-methyl-4-((4- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 112) N'-(2-chloro-4-((2-chloro-6-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimide amide;
(Serial number 113) N'-(2,5-dimethyl-4- (methyl (4- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 114) N'-(2-chloro-5-methyl-4- (methyl (4- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 115) N'-(2-chloro-5-methyl-4- (methyl (3- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 116) N'-(2,5-dimethyl-4-((2-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 117) N'-(2-chloro-5-methyl-4-((2-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 118) N'-(4-((3-((difluoromethyl) thio) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 119) N'-(2,5-dimethyl-4-((4-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 120) N'-(2-chloro-5-methyl-4-((4-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 121) N'-(2,5-dimethyl-4- (methyl (2-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 122) N'-(2-chloro-5-methyl-4- (methyl (2-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 123) N'-(2,5-dimethyl-4- (methyl (4-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 124) N'-(2-chloro-5-methyl-4- (methyl (4-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 125) N'-(4-((3-((difluoromethyl) thio) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 126) N'-(2,5-dimethyl-4-((3-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 127) N'-(2,5-dimethyl-4-((4- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 128) N'-(2-chloro-5-methyl-4-((4- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 129) N'-(2,5-dimethyl-4- (methyl (3-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 130) N'-(2-chloro-5-methyl-4- (methyl (3-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 131) N'-(2,5-dimethyl-4- (methyl (4- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 132) N'-(2-chloro-5-methyl-4- (methyl (4- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 133) N'-(2,5-dimethyl-4-((3- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 134) N'-(2-chloro-5-methyl-4-((3- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 135) N'-(2,5-dimethyl-4- (methyl (3- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 136) N'-(2-chloro-5-methyl-4- (methyl (3- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 137) N'-(4-((3,5-bis (trifluoromethyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 138) N'-(4-((3,5-bis (trifluoromethyl) phenyl) amino) -2-chloro-5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 139) N'-(2-chloro-5-methyl-4-((3-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 140) N'-(2-chloro-4-((4- (dimethylamino) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 141) N'-(4-((4- (dimethylamino) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 142) N'-(2-chloro-4-((3-((difluoromethyl) thio) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 143) N'-(2-chloro-4-((3-((difluoromethyl) thio) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 144) N'-(4-((3- (difluoromethoxy) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 145) N'-(4-((3- (difluoromethoxy) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 146) N'-(2-chloro-4-((3- (difluoromethoxy) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 147) N'-(2,5-dimethyl-4-((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 148) N'-(2,5-dimethyl-4-((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 149) N'-(2,5-dimethyl-4-((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 150) N'-(2-chloro-4-((4- (difluoromethoxy) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 151) N'-(4-((2,5-difluorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 152) N'-(2-chloro-4-((2,5-difluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 153) N'-(4-((3,5-bis (trifluoromethyl) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 154) N'-(4-((3,5-bis (trifluoromethyl) phenyl) (methyl) amino) -2-chloro-5-methylphenyl) -N-ethyl-N-methylformimide amide ;
(Serial number 155) N'-(2,5-dimethyl-4-((5-methyl-2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 156) N'-(4-((2,5-difluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 157) N'-(2-chloro-4-((2,5-difluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 158) N'-(2,5-dimethyl-4- (methyl (5-methyl-2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 159) N'-(4-((4-chloro-2- (trifluoromethyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 160) N'-(2-chloro-4-((4-chloro-2- (trifluoromethyl) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimide amide;
(Serial number 161) N'-(4-((4-chloro-2- (trifluoromethyl) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 162) N'-(2-chloro-4-((4-chloro-2- (trifluoromethyl) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimide Amide;
(Serial number 163) N'-(2-chloro-5-methyl-4- (methyl (2- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 164) N'-(2-chloro-4-((3- (difluoromethoxy) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimide amide;
(Serial number 165) N'-(2-chloro-5-methyl-4-((2- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 166) N'-(4-((2-chloro-4- (trifluoromethyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 167) N'-(2-chloro-4-((2-chloro-4- (trifluoromethyl) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimide amide;
(Serial number 168) N'-(4-((2-Chloro-4- (trifluoromethyl) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 169) N'-(2-chloro-4-((2-chloro-4- (trifluoromethyl) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimide Amide;
(Serial number 170) N'-(2,5-dimethyl-4-((2- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 171) N-ethyl-N'-(4-((4-fluoro-3- (1,1,2,2-tetrafluoroethoxy) phenyl) amino) -2,5-dimethylphenyl) -N- Methylformimide amide;
(Serial number 172) N'-(2-chloro-4-((4-fluoro-3- (1,1,2,2-tetrafluoroethoxy) phenyl) amino) -5-methylphenyl) -N-ethyl- N-Methylformimideamide;
(Serial number 173) 5-Chloro-N- (2-fluorophenyl) -N, 2-dimethyl-4-((morpholinomethylene) amino) aniline;
(Serial number 174) N'-(2-chloro-4- (N- (2-fluorophenyl) methylsulfonamide) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 175) N- (5-chloro-4-(((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (2-fluorophenyl) acetamide
(Serial number 176) N'-(2-chloro-4-((2-fluorophenyl) (methyl) amino) -5-methylphenyl) -N, N-dimethylformimideamide;
(Serial number 177) N'-(2-chloro-4- (ethyl (2-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 178) 5-Chloro-N- (2-fluorophenyl) -N, 2-dimethyl-4-((morpholinomethylene) amino) aniline;
(Serial number 179) 5-Chloro-N- (2-fluorophenyl) -N, 2-dimethyl-4-((thiomorpholinomethylene) amino) aniline;
(Serial number 180) N-ethyl-N'-(5-fluoro-4-((4-fluoro-3- (1,1,2,2-tetrafluoroethoxy) phenyl) amino) -2-methylphenyl)- N-Methylformimideamide;
(Serial number 181) N-ethyl-N'-(5-fluoro-4-((4-fluoro-3- (1,1,2,2-tetrafluoroethoxy) phenyl) (methyl) amino) -2-methyl) Phenyl) -N-methylformimideamide;
(Serial number 182) N- (5-chloro-4-(((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (2-chlorophenyl) acetamide;
(Serial number 183) N'-(2-chloro-4- (N- (2-chlorophenyl) methylsulfonamide) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 184) N'-(4-((4-((difluoromethyl) thio) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 185) N'-(2-chloro-4-((4-((difluoromethyl) thio) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 186) N'-(4-((4-((difluoromethyl) thio) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 187) N'-(2-chloro-4-((4-((difluoromethyl) thio) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 188) N'-(2-chloro-4- (ethyl (phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 189) N- (5-chloro-4-(((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N-phenylacetamide;
(Serial number 190) N'-(2-chloro-4-((2-((difluoromethyl) thio) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 191) N'-(2-chloro-4-((2-((difluoromethyl) thio) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 192) N'-(2-chloro-4- (ethyl (3-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 193) N'-(2-chloro-4-((3- (difluoromethoxy) -4-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimide amide;
(Serial number 194) N'-(2-chloro-4- (N- (3-methoxyphenyl) methylsulfonamide) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 195) N'-(4-((3- (difluoromethoxy) -4-fluorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 196) N'-(2-chloro-4-((3- (difluoromethoxy) -4-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide ;
(Serial number 197) N'-(4-((3- (difluoromethoxy) -4-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 198) N'-(4-((2,5-dimethylphenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 199) N'-(2-chloro-4-((2,5-dimethylphenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 200) N- (5-chloro-4-(((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (2-chlorophenyl) propionamide;
(Serial number 201) N-ethyl-N'-(5-fluoro-4-((4-methoxyphenyl) amino) -2-methylphenyl) -N-methylformimideamide;
(Serial number 202) N-ethyl-N'-(5-fluoro-4-((4-methoxyphenyl) (methyl) amino) -2-methylphenyl) -N-methylformimideamide;
(Serial number 203) N- (5-chloro-4-(((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (2-fluorophenyl) propionamide
(Serial number 204) N'-(2-Chloro-4- (N- (4-fluoro-3- (1,1,2,2-tetrafluoroethoxy) phenyl) methylsulfonamide) -5-methylphenyl)- N-ethyl-N-methylformimide amide;
(Serial number 205) N'-(2,5-dimethyl-4-((3- (1,1,2,2-tetrafluoroethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimide amide ;
(Serial number 206) N'-(2,5-dimethyl-4- (methyl (3- (1,1,2,2-tetrafluoroethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimide Amide;
(Serial number 207) N-ethyl-N'-(4-((2-fluoro-5-methylphenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 208) N-ethyl-N'-(5-fluoro-4-((2-fluorophenyl) amino) -2-methylphenyl) -N-methylformimideamide;
(Serial number 209) N-ethyl-N'-(4-((2-fluoro-5-methylphenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 210) N'-(2-chloro-4-((2-fluoro-5-methylphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 211) N-ethyl-N'-(5-fluoro-2-methyl-4- (phenylamino) phenyl) -N-methylformimideamide;
(Serial number 212) N'-(4-((2-chlorophenyl) amino) -5-fluoro-2-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 213) N'-(4-((4- (tert-butyl) phenyl) amino) -5-fluoro-2-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 214) N-ethyl-N'-(5-fluoro-2-methyl-4- (m-tolylamino) phenyl) -N-methylformimideamide;
(Serial number 215) N- (5-chloro-4-(((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N-phenylpropionamide;
(Serial number 216) N- (5-chloro-4-(((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (3-methoxyphenyl) acetamide;
(Serial number 217) N'-(2-chloro-4-((4-fluoro-3-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 218) N-ethyl-N'-(4-((4-fluoro-3-methoxyphenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 219) N-ethyl-N'-(4-((4-fluoro-3-methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 220) N'-(4-((2-((difluoromethyl) thio) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 221) N'-(4-((2-((difluoromethyl) thio) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 222) N'-(2-chloro-4-((4-fluoro-3-methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimide amide;
(Serial number 223) N'-(2-bromo-6-fluoro-3-methyl-4- (phenylamino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 224) N'-(2-chloro-5-methyl-4-((5-oxo-5,6,7,8-tetrahydronaphthalene-2-yl) amino) phenyl) -N-ethyl-N- Methylformimide amide;
(Serial number 225) N'-(2-bromo-6-fluoro-3-methyl-4- (methyl (phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 226) N'-(2-chloro-5-methyl-4-((1-methylindolin-5-yl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 227) N'-(2,5-dimethyl-4-((5-oxo-5,6,7,8-tetrahydronaphthalene-2-yl) amino) phenyl) -N-ethyl-N-methylform Imidamide;
(Serial number 228) N-ethyl-N'-(5-fluoro-2-methyl-4- (methyl (phenyl) amino) phenyl) -N-methylformimideamide;
(Serial number 229) N'-(4-((4- (tert-butyl) phenyl) (methyl) amino) -5-fluoro-2-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 230) N-ethyl-N'-(5-fluoro-2-methyl-4- (methyl (m-tolyl) amino) phenyl) -N-methylformimideamide;
(Serial number 231) N-ethyl-N'-(7-((2-methoxyphenyl) amino) -2,3-dihydro-1H-inden-4-yl) -N-methylformimideamide;
(Serial number 232) N-ethyl-N-methyl-N'-(7- (p-tolylamino) -2,3-dihydro-1H-inden-4-yl) formimideamide;
(Serial number 233) N'-(7-((4-chlorophenyl) amino) -2,3-dihydro-1H-inden-4-yl) -N-ethyl-N-methylformimideamide;
(Serial number 234) N-ethyl-N-methyl-N'-(4- (phenylamino) naphthalene-1-yl) formimideamide;
(Serial number 235) N'-(2,5-dimethyl-4- (pyridin-2-ylamino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 236) N'-(2,5-dimethyl-4- (methyl (pyridine-2-yl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 237) N'-(2-chloro-5-methyl-4- (pyridin-2-ylamino) phenyl) -N-ethyl-N-methylformimideamide;
The compound according to any one of Supplementary note 1, 2 or 3.

<Appendix 5>
A composition for controlling or preventing phytopathogenic microorganisms, which comprises the compound of the general formula (I) according to any one of Supplementary note 1 to 4 and one or more kinds of inert carriers.

<Appendix 6>
Compounds of the general formula (I) according to any one of Supplementary note 1 to 4, and / or fungicides, insecticides, nematicides, tick repellents, biopesticides, herbicides. , A composition comprising one or more active compatible compounds selected from plant growth regulators, antibiotics, fertilizers and / or mixtures thereof.

<Appendix 7>
Addendum 5 or 6 wherein the concentration of the compound having the general formula (I) is in the range of 1 to 90% by weight, preferably 5 to 50% by weight, based on the total weight of the composition. The composition according to.

<Appendix 8>
Of the general formula (I) according to any one of Supplementary note 1 to 4 for controlling phytopathogenic fungi, bacteria, insects, nematodes, and mites of agricultural crops and / or garden crops. Use of compounds.

<Appendix 9>
The compound of the general formula (I) according to any one of Supplementary note 1 to 4 or any one of Supplementary notes 5 to 7 for controlling or preventing phytopathogenic fungi of agricultural crops and / or horticultural crops. Use of the compositions described in section.

<Appendix 10>
The composition according to any one of Supplementary note 5 to 7, for controlling or preventing phytopathogenic fungi, bacteria, insects, nematodes, and mites of agricultural crops and / or garden crops. Use of things.

<Appendix 11>
Agricultural crops include grains, corn, rice, soybeans and other legumes, fruits and fruit trees, fruit and fruit trees, citrus and citrus fruit trees, any garden plant, Uridae, oily plants, tobacco, coffee, tea, cacao, The compound of the general formula (I) according to any one of Supplementary note 1 to 4, which is a sugar daikon, sugar cane, cotton, potato, tomato, onion, peppers and other plants, and an ornamental plant, or a supplementary note. Use of the composition according to any one of 5 to 7.

<Appendix 12>
A method for controlling or preventing infection of phytopathogenic microorganisms in useful plants in agricultural crops and / or garden crops, from the compound of the general formula (I) described in any one of Supplementary note 1 to 4 or from Supplementary note 5. 7. A method in which the composition according to any one of 7 is applied to a plant, a part thereof or a topic thereof.

<Appendix 13>
A method for controlling or preventing infection of phytopathogenic microorganisms in useful plants in agricultural crops and / or garden crops, from the compound of the general formula (I) described in any one of Supplementary note 1 to 4 or from Supplementary note 5. 7. A method in which the composition according to any one of 7 is applied to plant seeds.

<Appendix 14>
Plant-pathogenic microorganisms in crops and / or horticultural crops using the compound of the general formula (I) according to any one of Supplements 1 to 4 or the composition according to any one of Supplements 5 to 7. A method comprising the application of an effective dose of a compound or composition in an amount ranging from 1 g to 5 kg per hectare of a crop or horticultural crop.

Claims (13)

Compound of formula (I)

During the ceremony
R ¹ is hydrogen, CN, C 1-6 _- alkyl, C _1-6 -alkoxy, C _{1-6 -} alkylthio, C2-6 _- alkenyl, C2-6 _- alkynyl, C1-6 _- haloalkyl and Selected from the group consisting of C _3-8 -cycloalkyl ,;
R ² is C _1-6 -alkyl,
R ³ is hydrogen, OR' , C _1-12 -alkyl, C _2-12 -alkenyl, C _2-12 -alkynyl, C _1-12 -haloalkyl, C _2-12 -haloalkenyl, C _2-12- Selected from the group consisting of haloalkynyl, C _3-8 -cycloalkyl ; in a cyclic ring system, one or more carbon atoms are hetero selected from the group consisting of N, O, and S (O) _n . May be replaced by an atom; or
R ² and R ³ are with the atoms to which they are attached, or with additional atoms selected from the group consisting of C, N, O, S, as well as C (= O), C (= S), S ( O) 1 to 3 ring members selected from the group consisting of _m and _SiR'2 may be optionally included to form a 4 to 7 member non-aromatic ring, further one or more. May be substituted with X, R', OR', SR', _NR'2 , _SiR'3 , COOR', CN, and CONR'2; ^each group of ^{R1 ,} _R2 and R3 It may be optionally substituted with one or more groups selected from the group consisting of X, R', OR'and CN ;
R ⁴ and R ⁵ are independently hydrogen, X, CN, S (O) _n R'', OR'', C 1-6 _- alkyl, C2-6 _- alkoxy, C2-6 _- alkynyl. , C _{1-6 -} haloalkyl, C2-6 -haloalkenyl, C2-6 _- haloalkynyl, C1-6 _{- haloalkoxy} , C1-6 -haloalkylthio, C3-8 _- cycloalkyl, _C4 Selected from the group consisting of _{~ 8} -cycloalkenyl, _{C5-8 -} cycloalkoxynyl, C3-8-cycloalkyloxy, C3-8-cycloalkylthio, phenyl, benzyl ; one or more in the cyclic ring system. Multiple carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, and S (O) _n ; all of the above groups are X, R', OR', SR', It may be optionally substituted with one or more groups selected from the group consisting of _NR'2 and CN ;
R ⁶ and R ⁷ independently consist of hydrogen, X, OR', C _1-6 -alkyl, C _2-6 -alkenyl, C _1-6 -haloalkyl, and C 3-6 _- cycloalkyl. Selected from; or with ^R4 and ^R7 or ^R5 and ^R6 with the atoms to which they are attached, or with additional atoms selected from the group consisting of C, N, O, S, and C (= A 4- to 7-membered ring may be formed by optionally including 1 to 3 ring members selected from the group consisting of O), C (= S), S (O) _m and _SiR'2 . This ring may be partially substituted with one or more X, R', OR', SR', NR' ₂ and CN ; of R ⁴ , R ⁵ , R ⁶ and R ⁷ . All groups may be optionally substituted with one or more groups selected from the group consisting of X, R', OR', SR', _NR'2 , and CN ;
R ⁸ is hydrogen, S (O) _n R'' , _SiR'3 , NR'R'', (C = O) -R'', C1-6 _- alkyl, C2-6 _- alkenyl, C. _{2-6 -} alkynyl, C1-6 _- haloalkyl, C2-6 _- haloalkenyl, C2-6 - haloalkynyl, C3-8 _- cycloalkyl, _{C4-8 -} cycloalkenyl, C5-8- Selected from the group consisting of cycloalkynyl, C _3-4 heterocyclyl, C _3-4 -heterocyclyl alkyl; in a cyclic ring system, one or more carbon atoms consist of N, O, and S (O) _n . It may be replaced by a heteroatom selected from the group; all of the above groups may be one or more selected from the group consisting of X, R', OR', SR', _NR'2 , and CN . It may be substituted with a group; or A is selected from the group consisting of condensed or non-condensed C _6-10 -aryl, C _5-10 -heteroaryl, and one or more carbon atoms are N, O. , C (= O), C (= S), S (O) _m and ^SiR'2 replaced by a heteroatom selected from S, and optionally by one or _more groups of R9. Includes 1 to 3 ring members selected from the group consisting of;
R ⁹ is hydrogen, X, CN, SCN, SF ₅ , R'', OR'', NO ₂ , NR'' ₂ , _SiR'3 , (C = O) -R'', S (O) _n . R'', OS (O) _n R'', _OSiR'3 , NR'S (O) _n R'', 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} -Alkayl, 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, C1-12 _- alkylthio, C1-12-haloalkoxy, _C1-12 -haloalkylthio, C3-12 _- cycloalkyl, _{C4-8 -} cycloalkenyl, C5-8- Cycloalkynyl, C _3-8 -cycloalkyloxy, C _3-8 -cycloalkylthio, C _7-19 -aralkyl, C _7-19 -alkali; bicyclic C _5-12 -alkyl, C _7-12- Selected from the group consisting of alkenyl; in the cyclic ring system, one or more carbon atoms may be replaced by heteroatoms selected from the group consisting of N, O, and S (O) _n ; All of the above groups are replaced by one or _more groups selected from the group consisting of X, R', OR', SR', _NR'2 , _SiR'3 , COOR', CN, and CONR'2. May be; or two ^R9s , with the atoms to which they are attached, or with additional atoms selected from the group consisting of C, N, O, S, as well as C (= O), C (=). A 4- to 10-membered ring may be optionally included to optionally include 1 to 3 ring members selected from the group consisting of S), S (O) _m and _SiR'2 , with one more ring. Alternatively, it may be substituted with a plurality of X, R', OR', SR', _NR'2 , _SiR'3 , COOR', CN, and _CONR'2 ;
The groups of R ⁸ and R ⁹ are all selected from the group consisting of X, R', OR', SR', _NR'2 , _SiR'3 , COOR', CN, and _CONR'2 . It may be optionally substituted by the group;
X represents halogen;
R'represents a linear or branched chain C _1-12- alkyl or cyclic C _3-10 -alkyl optionally substituted with hydrogen, one or more Xs;
R'' is hydrogen; _NR'2 , OR', straight chain or branched chain C _1-12 -alkyl, C _1-12 -haloalkyl, cyclic C _3-8 -alkyl, X, R', OR One or more Rs optionally substituted by one or _more groups selected from the group consisting of', SR', _NR'2 , _SiR'3 , COOR', CN, and CONR'2. Represents a _C5-18 -aryl optionally substituted by';
m and n represent integers, n = 0, 1 or 2; m = 1 or 2) compound,
And these agriculturally acceptable salts, metal complexes, stereoisomers , diastereoisomers, enantiomers, or N-oxides. Each substituent is independently selected from the following:
^R1 is selected from the group consisting of hydrogen, C1-6 _- alkyl, C1-6 _- alkoxy, C1-6 _- alkylthio, C1-6 _- haloalkyl or C3-8 _- cycloalkyl;
R3 is C1-6 ^- alkyl, C2-6 _- alkenyl, C2-6 _- alkynyl, C1-6 _- alkoxy, C1-6 _- alkylthio, C1-6 _- haloalkyl or _{C3-8 .} -Selected from the group consisting of cycloalkyl;
R ⁴ and R ⁵ independently X, CN, S (O) _n R'', NR'R'', (C = O) -R'', CR'= NR'', C _{1 to} Consists of ₆ -alkyl, C2-6 _- alkenyl, C2-6 _- alkynyl, C1-6 _- haloalkyl, C1-6 _- haloalkylthio , C3-8 _- cycloalkyl or C3-8 _- cycloalkylthio Selected from the group ;
R ⁶ and R ⁷ are independently selected from the group consisting of hydrogen, X, CN, C _1-6 -alkyl, C _1-6 -haloalkyl or C 3-8 _- cycloalkyl; or
R ⁸ is hydrogen, CN, S (O) _n R'', NR'R'', (C = O) -R'', CR'= NR'', C1-6 _- alkyl, _C2- Selected from the group consisting of ₆ -alkenyl, C2-6 _- alkynyl, C1-6 _- haloalkyl, C3-8 _- cycloalkyl, C3-8 _- heterocyclyl or C3-8 _- heterocyclylalkyl;
A is phenyl, naphthalenyl, frill, thienyl, pyrrolyl, isooxazolyl, isothiazolyl, pyrazolyl, oxazolyl, imidazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyridadinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, benzoimidazolyl, indazolyl, indyl. Selected from the group consisting of phenyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinazolinyl or cinnonyl, each A being replaced with one or more ^R9s ;
R ⁹ is X, CN, SCN, SF ₅ , R'', OR'', NO ₂ , NR'' ₂ , _SiR'3 , (C = O) -R'', S (O) _n R'' , OS (O) _n R'', _OSiR'3 , NR'S (O) _n R'', C _1-8 -alkyl-S (O) _n R'', C _1-6 -alkyl- (C) = O) -R'', CR'= NR'', C2-6-alkenyl, C2-6 _- alkynyl, C1-6 _- haloalkyl, C2-6 _- haloalkenyl, _{C1-12 -} alkoxy , C _{1-12 -} alkylthio, C1-12 _- haloalkoxy, C1-12-haloalkylthio, C _{3-8 -} cycloalkyl, C4-8-cycloalkenyl, C3-8 _- cycloalkyloxy or C Selected from the group consisting of _3-8 -cycloalkylthio, or two ^R9s with additional atoms selected from the atom to which they are attached, or from the group consisting of C, N, O, S, as well as A 4- to 10-membered ring is formed by optionally including 1 to 3 ring members selected from the group consisting of C (= O), C (= S), S (O) _m and _SiR'2 . Often, this ring may be partially substituted with one or more X, R', OR', SR', NR' ₂ , SiR' ₃ , COOR', CN, and _CONR'2 . Often;
Claims that R ¹ to R ⁹ may be further optionally substituted with one or more groups selected from the group consisting of X, R'', OR', SR', NR' ₂ and CN . Item 1, the compound of the formula (I),
And these agriculturally acceptable salts, stereoisomers , diastereoisomers, enantiomers or N-oxides. Each substituent is independently selected from the following:
R ¹ is hydrogen or C _1-6 -alkyl;
^R2 is methyl and
R ³ is C _1-6 -alkyl or C _1-6 -haloalkyl;
R ⁴ and R ⁵ are independently selected from the group consisting of X, CN, C _1-6 -alkyl, C _1-6 -haloalkyl or C _3-8 -cycloalkyl;
R ⁶ and R ⁷ are independently selected from the group consisting of hydrogen, X, C _1-6 -alkyl, C _1-6 -haloalkyl;
R ⁸ is hydrogen, CN, S (O) _n R'', (C = O) -R'', C _1-6 -alkyl, C _1-6 -haloalkyl, C _2-6 -alkenyl, C _{2 ~ 6 -} alkynyl, C3-8 _- cycloalkyl, C3-6-heterocyclyl or C3-6-heterocyclylalkyl;
Select from the group consisting of phenyl, naphthalenyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, oxazolylisooxazolyl, oxadiazolyl, pyridinyl, pyridadinyl, pyrimidinyl, pyrazinyl and quinolinyl in which A is substituted with one or more ^R9s . Beed ;
R ⁹ is X, CN, R'' , OR'', NO ₂ , NR'' ₂ , SiR'3 _, S (O) _n R'', C _1-6 -alkyl , 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, C4-8 _- cycloalkenyl, C3-8-cycloalkyloxy, C3-8 _- cycloalkylthio ;
Claims that R ¹ to R ⁹ may be further optionally substituted with one or more groups selected from the group consisting of X, R'', OR', SR', NR' ₂ and CN . The compound of the formula (I) according to Item 1 or 2 .
And an agriculturally acceptable salt, stereoisomer , diastereoisomer, enantiomer or N-oxide of the compound. The compound of the general formula (I) is
(Serial number 1) N'-(2,5-dimethyl-4- (phenylamino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 2) N'-(2,5-dimethyl-4- (methyl (phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 3) N'-(2-chloro-5-methyl-4- (phenylamino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 4) N'-(2-chloro-5-methyl-4- (methyl (phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 5) N'-(2,5-dimethyl-4- (N-phenylmethylsulfonamide) phenyl) -N-ethyl-N-methylformimideamide;
(Serial No. 6) N'-(2,5-dimethyl-4- (methyl (2-methyl-4- (perfluoropropane-2-yl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide ;
(Serial number 7) N'-(4-((4-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 8) N'-(4-((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 9) N'-(4-((3,4-dichlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 10) N'-(2-chloro-5-methyl-4- (methyl (3,4,5-trifluorophenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 11) N'-(2-chloro-5-methyl-4- (methyl (m-tolyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 12) N'-(2-chloro-4-((3,4-dichlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 13) N'-(2-chloro-4-((3-methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 14) N'-(2-chloro-5-methyl-4- (methyl (4- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 15) N'-(2-chloro-5-methyl-4- (methyl (p-tolyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 16) N'-(2-chloro-4-((2-methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 17) N'-(2-chloro-5-methyl-4- (N-phenylmethylsulfonamide) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 18) N'-(2-chloro-4-((2-chlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 19) N'-(2-chloro-4-((4-chlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 20) N'-(2-chloro-4-((4-methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 21) N'-(2-chloro-4-((4-methoxy-3-methylphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimide amide;
(Serial number 22) N'-(2-chloro-4-((3,4-dimethoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 23) N'-(2-chloro-4-((3,5-dimethoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 24) N'-(2,5-dimethyl-4- (methyl (m-tolyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 25) N-ethyl-N'-(4-((3-methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 26) N'-(2,5-dimethyl-4- (methyl (p-tolyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 27) N-ethyl-N'-(4-((4-Methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 28) N-ethyl-N'-(4-((3-methoxyphenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 29) N'-(2,5-dimethyl-4- (m-tolylamino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 30) N'-(2,5-dimethyl-4- (p-tolylamino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 31) N'-(4-((4- (tert-butyl) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 32) N'-(4-((4- (tert-butyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 33) N'-(4-((2-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 34) N'-(2-chloro-4-((2-chlorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 35) N-ethyl-N'-(4-((2-fluorophenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 36) N-ethyl-N'-(4-((2-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 37) N'-(2-chloro-4-((2-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 38) N-ethyl-N'-(4-((3-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 39) N-ethyl-N'-(4-((4-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 40) N'-(4-((2-chlorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 41) N- (4-(((Ethyl (methyl) amino) methylene) amino) -2,5-dimethylphenyl) -N-phenylacetamide;
(Serial number 42) N'-(2-chloro-5-methyl-4- (methyl (pyridine-2-yl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 43) N'-(4-((4-chlorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 44) N-ethyl-N'-(4-((4-fluorophenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 45) N-ethyl-N'-(4-((2-methoxyphenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 46) N-ethyl-N'-(4-((3-fluorophenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 47) N'-(2-chloro-4-((2-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 48) N'-(2-chloro-4-((3-chlorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 49) N- (3-chlorophenyl) -N, 2,5-trimethyl-4-((morpholinomethylene) amino) aniline;
(Serial number 50) N'-(2-chloro-4-((3-chlorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 51) N- (3-chlorophenyl) -N, 2,5-trimethyl-4-((piperidine-1-ylmethylene) amino) aniline;
(Serial number 52) N-allyl-N'-(4-((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 53) N'-(4-((3-chlorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-isopropyl-N-methylformimideamide;
(Serial number 54) N'-(4-((2-bromophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 55) N'-(4-((3-chlorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 56) N-ethyl-N'-(4-((4-methoxyphenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 57) N'-(2,5-dimethyl-4-((2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 58) N'-(2,5-dimethyl-4- (methyl (2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 59) N'-(2,5-dimethyl-4-((4- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 60) N'-(2,5-dimethyl-4-((3- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 61) N'-(2,5-dimethyl-4- (methyl (4- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 62) N'-(2,5-dimethyl-4- (methyl (3- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 63) N'-(2,5-dimethyl-4-((3- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 64) N'-(4-((2-bromophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 65) N-ethyl-N'-(4-((2-methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 66) N'-(2,5-dimethyl-4- (methyl (3- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 67) N'-(2-chloro-5-methyl-4-((3- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 68) N'-(2-chloro-5-methyl-4- (m-tolylamino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 69) N'-(2-chloro-4-((3-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 70) N'-(2-chloro-5-methyl-4- (o-tolylamino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 71) N'-(2-chloro-4-((4-chlorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 72) N'-(2,5-dimethyl-4- (o-tolylamino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 73) N'-(2-chloro-4-((4-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 74) N'-(2-chloro-5-methyl-4- (methyl (o-tolyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 75) N'-(4-((2-bromophenyl) amino) -2-chloro-5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 76) N'-(4-((2-bromophenyl) (methyl) amino) -2-chloro-5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 77) N'-(2,5-dimethyl-4- (methyl (o-tolyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 78) N'-(2-chloro-4-((2-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 79) N'-(2-chloro-5-methyl-4-((2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 80) N'-(2-chloro-5-methyl-4- (methyl (2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 81) N'-(2-chloro-5-methyl-4-((4- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 82) N'-(2-chloro-4-((3-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 83) N'-(2-chloro-4-((4-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 84) N'-(2-chloro-4-((3-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 85) N'-(2-chloro-4-((4-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 86) N'-(2,5-dimethyl-4-((3- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 87) N'-(2-chloro-5-methyl-4-((3- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 88) N'-(2-chloro-5-methyl-4- (methyl (3- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 89) N'-(2,5-dimethyl-4- (methyl (3- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 90) N'-(4-((2,6-difluorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 91) N'-(2-chloro-4-((2,6-difluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 92) N'-(4-((2,6-difluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 93) N'-(2-chloro-4-((2,6-difluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 94) N'-(4-((2-chloro-6-fluorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 95) N'-(2-chloro-4-((2-chloro-6-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 96) N'-(4-((2-Chloro-6-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 97) N'-(2,5-dimethyl-4-((4- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 98) N'-(4-((2,6-dichloro-4- (trifluoromethyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 99) N'-(2,5-dimethyl-4-((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 100) N'-(2-chloro-5-methyl-4-((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 101) N'-(2-chloro-5-methyl-4-((3- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 102) N'-(2,5-dimethyl-4-((4- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 103) N'-(2-chloro-5-methyl-4-((4- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 104) N'-(2,5-dimethyl-4- (methyl (2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 105) N'-(2-chloro-5-methyl-4- (methyl (2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 106) N'-(2,5-dimethyl-4- (methyl (4- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 107) N'-(2-chloro-5-methyl-4- (methyl (4- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 108) N'-(2-chloro-5-methyl-4- (methyl (3- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 109) N'-(2-Chloro-5-methyl-4- (N-phenylethyl sulfonamide) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 110) N'-(2-chloro-4-((2,4-dichloro-6- (trifluoromethyl) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide ;
(Serial number 111) N'-(2-chloro-5-methyl-4-((4- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 112) N'-(2-chloro-4-((2-chloro-6-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimide amide;
(Serial number 113) N'-(2,5-dimethyl-4- (methyl (4- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 114) N'-(2-chloro-5-methyl-4- (methyl (4- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 115) N'-(2-chloro-5-methyl-4- (methyl (3- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 116) N'-(2,5-dimethyl-4-((2-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 117) N'-(2-chloro-5-methyl-4-((2-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 118) N'-(4-((3-((difluoromethyl) thio) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 119) N'-(2,5-dimethyl-4-((4-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 120) N'-(2-chloro-5-methyl-4-((4-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 121) N'-(2,5-dimethyl-4- (methyl (2-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimide amide;
(Serial number 122) N'-(2-chloro-5-methyl-4- (methyl (2-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimide amide;
(Serial number 123) N'-(2,5-dimethyl-4- (methyl (4-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 124) N'-(2-chloro-5-methyl-4- (methyl (4-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 125) N'-(4-((3-((difluoromethyl) thio) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 126) N'-(2,5-dimethyl-4-((3-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 127) N'-(2,5-dimethyl-4-((4- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 128) N'-(2-chloro-5-methyl-4-((4- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 129) N'-(2,5-dimethyl-4- (methyl (3-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 130) N'-(2-chloro-5-methyl-4- (methyl (3-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 131) N'-(2,5-dimethyl-4- (methyl (4- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 132) N'-(2-chloro-5-methyl-4- (methyl (4- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 133) N'-(2,5-dimethyl-4-((3- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 134) N'-(2-chloro-5-methyl-4-((3- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 135) N'-(2,5-dimethyl-4- (methyl (3- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 136) N'-(2-chloro-5-methyl-4- (methyl (3- (pentafluoro-l6-sulfaneyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 137) N'-(4-((3,5-bis (trifluoromethyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 138) N'-(4-((3,5-bis (trifluoromethyl) phenyl) amino) -2-chloro-5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 139) N'-(2-chloro-5-methyl-4-((3-((trifluoromethyl) thio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 140) N'-(2-chloro-4-((4- (dimethylamino) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 141) N'-(4-((4- (dimethylamino) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 142) N'-(2-chloro-4-((3-((difluoromethyl) thio) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 143) N'-(2-chloro-4-((3-((difluoromethyl) thio) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 144) N'-(4-((3- (difluoromethoxy) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 145) N'-(4-((3- (difluoromethoxy) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 146) N'-(2-chloro-4-((3- (difluoromethoxy) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 149) N'-(2,5-dimethyl-4-((2- (trifluoromethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 150) N'-(2-chloro-4-((4- (difluoromethoxy) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimide amide;
(Serial number 151) N'-(4-((2,5-difluorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 152) N'-(2-chloro-4-((2,5-difluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 153) N'-(4-((3,5-bis (trifluoromethyl) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 154) N'-(4-((3,5-bis (trifluoromethyl) phenyl) (methyl) amino) -2-chloro-5-methylphenyl) -N-ethyl-N-methylformimideamide ;
(Serial number 155) N'-(2,5-dimethyl-4-((5-methyl-2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 156) N'-(4-((2,5-difluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 157) N'-(2-chloro-4-((2,5-difluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 158) N'-(2,5-dimethyl-4- (methyl (5-methyl-2- (trifluoromethyl) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 159) N'-(4-((4-chloro-2- (trifluoromethyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 160) N'-(2-chloro-4-((4-chloro-2- (trifluoromethyl) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimide amide;
(Serial number 161) N'-(4-((4-chloro-2- (trifluoromethyl) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 162) N'-(2-chloro-4-((4-chloro-2- (trifluoromethyl) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimide Amide;
(Serial number 163) N'-(2-chloro-5-methyl-4- (methyl (2- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 164) N'-(2-chloro-4-((3- (difluoromethoxy) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimide amide;
(Serial number 165) N'-(2-chloro-5-methyl-4-((2- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 166) N'-(4-((2-chloro-4- (trifluoromethyl) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 167) N'-(2-chloro-4-((2-chloro-4- (trifluoromethyl) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimide amide;
(Serial number 168) N'-(4-((2-Chloro-4- (trifluoromethyl) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 169) N'-(2-chloro-4-((2-chloro-4- (trifluoromethyl) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimide Amide;
(Serial number 170) N'-(2,5-dimethyl-4-((2- (methylthio) phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 171) N-ethyl-N'-(4-((4-fluoro-3- (1,1,2,2-tetrafluoroethoxy) phenyl) amino) -2,5-dimethylphenyl) -N- Methylformimide amide;
(Serial number 172) N'-(2-chloro-4-((4-fluoro-3- (1,1,2,2-tetrafluoroethoxy) phenyl) amino) -5-methylphenyl) -N-ethyl- N-Methylformimideamide;
(Serial number 173) 5-Chloro-N- (2-fluorophenyl) -N, 2-dimethyl-4-((morpholinomethylene) amino) aniline;
(Serial number 174) N'-(2-chloro-4- (N- (2-fluorophenyl) methylsulfonamide) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 175) N- (5-chloro-4-(((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (2-fluorophenyl) acetamide
(Serial number 176) N'-(2-chloro-4-((2-fluorophenyl) (methyl) amino) -5-methylphenyl) -N, N-dimethylformimideamide;
(Serial number 177) N'-(2-chloro-4- (ethyl (2-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 179) 5-Chloro-N- (2-fluorophenyl) -N, 2-dimethyl-4-((thiomorpholinomethylene) amino) aniline;
(Serial number 180) N-ethyl-N'-(5-fluoro-4-((4-fluoro-3- (1,1,2,2-tetrafluoroethoxy) phenyl) amino) -2-methylphenyl)- N-Methylformimideamide;
(Serial number 181) N-ethyl-N'-(5-fluoro-4-((4-fluoro-3- (1,1,2,2-tetrafluoroethoxy) phenyl) (methyl) amino) -2-methyl) Phenyl) -N-methylformimideamide;
(Serial number 182) N- (5-chloro-4-(((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (2-chlorophenyl) acetamide;
(Serial number 183) N'-(2-chloro-4- (N- (2-chlorophenyl) methylsulfonamide) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 184) N'-(4-((4-((difluoromethyl) thio) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 185) N'-(2-chloro-4-((4-((difluoromethyl) thio) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 186) N'-(4-((4-((difluoromethyl) thio) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 187) N'-(2-chloro-4-((4-((difluoromethyl) thio) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 188) N'-(2-chloro-4- (ethyl (phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 189) N- (5-chloro-4-(((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N-phenylacetamide;
(Serial number 190) N'-(2-chloro-4-((2-((difluoromethyl) thio) phenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 191) N'-(2-chloro-4-((2-((difluoromethyl) thio) phenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 192) N'-(2-chloro-4- (ethyl (3-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 193) N'-(2-chloro-4-((3- (difluoromethoxy) -4-fluorophenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimide amide;
(Serial number 194) N'-(2-chloro-4- (N- (3-methoxyphenyl) methylsulfonamide) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 195) N'-(4-((3- (difluoromethoxy) -4-fluorophenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 196) N'-(2-chloro-4-((3- (difluoromethoxy) -4-fluorophenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide ;
(Serial number 197) N'-(4-((3- (difluoromethoxy) -4-fluorophenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 198) N'-(4-((2,5-dimethylphenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 199) N'-(2-chloro-4-((2,5-dimethylphenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 200) N- (5-chloro-4-(((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (2-chlorophenyl) propionamide;
(Serial number 201) N-ethyl-N'-(5-fluoro-4-((4-methoxyphenyl) amino) -2-methylphenyl) -N-methylformimideamide;
(Serial number 202) N-ethyl-N'-(5-fluoro-4-((4-methoxyphenyl) (methyl) amino) -2-methylphenyl) -N-methylformimideamide;
(Serial number 203) N- (5-chloro-4-(((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (2-fluorophenyl) propionamide
(Serial number 204) N'-(2-chloro-4- (N- (4-fluoro-3- (1,1,2,2-tetrafluoroethoxy) phenyl) methylsulfonamide) -5-methylphenyl)- N-ethyl-N-methylformimide amide;
(Serial number 205) N'-(2,5-dimethyl-4-((3- (1,1,2,2-tetrafluoroethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimide amide ;
(Serial number 206) N'-(2,5-dimethyl-4- (methyl (3- (1,1,2,2-tetrafluoroethoxy) phenyl) amino) phenyl) -N-ethyl-N-methylformimide Amide;
(Serial number 207) N-ethyl-N'-(4-((2-fluoro-5-methylphenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 208) N-ethyl-N'-(5-fluoro-4-((2-fluorophenyl) amino) -2-methylphenyl) -N-methylformimideamide;
(Serial number 209) N-ethyl-N'-(4-((2-fluoro-5-methylphenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 210) N'-(2-chloro-4-((2-fluoro-5-methylphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimide amide;
(Serial number 211) N-ethyl-N'-(5-fluoro-2-methyl-4- (phenylamino) phenyl) -N-methylformimideamide;
(Serial number 212) N'-(4-((2-chlorophenyl) amino) -5-fluoro-2-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 213) N'-(4-((4- (tert-butyl) phenyl) amino) -5-fluoro-2-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 214) N-Ethyl-N'-(5-fluoro-2-methyl-4- (m-tolylamino) phenyl) -N-methylformimideamide;
(Serial number 215) N- (5-chloro-4-(((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N-phenylpropionamide;
(Serial number 216) N- (5-chloro-4-(((ethyl (methyl) amino) methylene) amino) -2-methylphenyl) -N- (3-methoxyphenyl) acetamide;
(Serial number 217) N'-(2-chloro-4-((4-fluoro-3-methoxyphenyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 218) N-ethyl-N'-(4-((4-fluoro-3-methoxyphenyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 219) N-ethyl-N'-(4-((4-fluoro-3-methoxyphenyl) (methyl) amino) -2,5-dimethylphenyl) -N-methylformimideamide;
(Serial number 220) N'-(4-((2-((difluoromethyl) thio) phenyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 221) N'-(4-((2-((difluoromethyl) thio) phenyl) (methyl) amino) -2,5-dimethylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 222) N'-(2-chloro-4-((4-fluoro-3-methoxyphenyl) (methyl) amino) -5-methylphenyl) -N-ethyl-N-methylformimide amide;
(Serial number 223) N'-(2-bromo-6-fluoro-3-methyl-4- (phenylamino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 224) N'-(2-chloro-5-methyl-4-((5-oxo-5,6,7,8-tetrahydronaphthalene-2-yl) amino) phenyl) -N-ethyl-N- Methylformimide amide;
(Serial number 225) N'-(2-bromo-6-fluoro-3-methyl-4- (methyl (phenyl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 226) N'-(2-chloro-5-methyl-4-((1-methylindoline-5-yl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 227) N'-(2,5-dimethyl-4-((5-oxo-5,6,7,8-tetrahydronaphthalene-2-yl) amino) phenyl) -N-ethyl-N-methylform Imidamide;
(Serial number 228) N-ethyl-N'-(5-fluoro-2-methyl-4- (methyl (phenyl) amino) phenyl) -N-methylformimideamide;
(Serial number 229) N'-(4-((4- (tert-butyl) phenyl) (methyl) amino) -5-fluoro-2-methylphenyl) -N-ethyl-N-methylformimideamide;
(Serial number 230) N-ethyl-N'-(5-fluoro-2-methyl-4- (methyl (m-tolyl) amino) phenyl) -N-methylformimideamide;
(Serial number 231) N-ethyl-N'-(7-((2-methoxyphenyl) amino) -2,3-dihydro-1H-inden-4-yl) -N-methylformimideamide;
(Serial number 232) N-ethyl-N-methyl-N'-(7- (p-tolylamino) -2,3-dihydro-1H-inden-4-yl) formimideamide;
(Serial number 233) N'-(7-((4-chlorophenyl) amino) -2,3-dihydro-1H-inden-4-yl) -N-ethyl-N-methylformimideamide;
(Serial number 234) N-ethyl-N-methyl-N'-(4- (phenylamino) naphthalene-1-yl) formimideamide;
(Serial number 235) N'-(2,5-dimethyl-4- (pyridin-2-ylamino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 236) N'-(2,5-dimethyl-4- (methyl (pyridine-2-yl) amino) phenyl) -N-ethyl-N-methylformimideamide;
(Serial number 237) N'-(2-chloro-5-methyl-4- (pyridin-2-ylamino) phenyl) -N-ethyl-N-methylformimideamide;
The compound according to any one of claims 1, 2 or 3. A composition for controlling or preventing phytopathogenic microorganisms, which comprises the compound of the formula (I) according to any one of claims 1 to 4 and / or one or more kinds of inert carriers. It contains the compound of the formula (I) according to claim 5 , and further contains a fungicides, an insecticide, a nematicides, a tick repellent, a biopesticide, a herbicide, a plant growth regulator, and an antibiotic. A composition comprising one or more active compatible compounds selected from substances, fertilizers and / or mixtures thereof. The composition according to claim 5 or 6, wherein the concentration of the compound of the formula (I) is in the range of 1 to 90% by weight based on the total weight of the composition. Of the formula (I) according to any one of claims 1 to 4, for controlling phytopathogenic fungi, bacteria, insects, nematodes, and mites of crops and / or garden crops. Use of a compound or the composition according to any one of claims 5 to 7 . The compound of the formula (I) according to any one of claims 1 to 4 or any of claims 5 to 7 for controlling or preventing phytopathogenic fungi of agricultural crops and / or garden crops. Use of the composition according to paragraph 1. Agricultural crops include grains, corn, rice, soybeans and other legumes, fruits and fruit trees, fruit and fruit trees, citrus and citrus fruit trees, any garden plant, Uridae, oily plants, tobacco, coffee, tea, cacao, The compound of formula (I) according to any one of claims 1 to 4, which is a sugar cane, sugar cane, cotton, potato, tomato, onion, peppers and other plants, and an ornamental plant, or a claim. Use of the composition according to any one of Items 5 to 7. A method for controlling or preventing infection of a phytopathogenic microorganism in a useful plant in an agricultural crop and / or a garden crop, wherein the compound of the formula (I) according to any one of claims 1 to 4 or claim 5 A method in which the composition according to any one of 7 to 7 is applied to a plant, a part thereof or a topic thereof. A method for controlling or preventing infection of a phytopathogenic microorganism in a useful plant in an agricultural crop and / or a garden crop, wherein the compound of the formula (I) according to any one of claims 1 to 4 or claim 5 A method in which the composition according to any one of 7 to 7 is applied to plant seeds. Plant pathogenicity in crops and / or horticultural crops using the compound of formula (I) according to any one of claims 1 to 4 or the composition according to any one of claims 5 to 7. A method for controlling or preventing microorganisms, comprising applying an effective dose of a compound or composition in an amount ranging from 1 g to 5 kg per hectare of crop or horticultural crop.