Substituted anilide derivative, its intermediate compound, chemicals for control of agricultural and fruit crop pests and their using

FIELD: organic chemistry, agriculture, insecticides.

SUBSTANCE: invention relates to a substituted anilide derivative of the formula (I): wherein R1 represents hydrogen atom, (C1-C6)-alkyl group; R2 represents hydrogen atom, halogen atom or halogen-(C1-C6)-alkyl group; R3 represents hydrogen atom, halogen atom, (C1-C6)-alkyl group, hydroxyl group or (C1-C6)-alkoxy-group; t = 1; m = 0; each among X that can be similar or different represents (C2-C8)-alkyl group, hydroxy-(C1-C6)-alkyl group or (C3-C6)-cycloalkyl-(C1-C6)-alkyl group; n = 1 or 2; Z represents oxygen atom; Q means a substitute represented by any of the following formulae: Q1-Q3, Q6, Q8-Q12, Q14-Q19, Q21 and Q23 (wherein each among Y1 that can be similar or different represents halogen atom, (C1-C6)-alkyl group, and so on); Y2 represents (C1-C6)-alkyl group or halogen-(C1-C6)-alkyl group; Y3 represents (C1-C6)-alkyl group, halogen-(C1-C6)-alkyl group or substituted phenyl group; p represents a whole number from 1 to 2; q represents a whole number from 0 or 2; r represents a whole number from 0 to 2. Also, invention proposes a chemical for control of pests of agricultural and fruit crops. The chemical comprises substituted anilide derivative of the formula (I) as an active component and represents insecticide, fungicide or acaricide. Also, invention proposes a method for addition of the chemical for control of pests of agricultural and fruits crops. Also, invention proposes aniline derivative represented by the general formula (II): wherein R1 represents hydrogen atom, (C1-C6)-alkyl group; R2 represents hydrogen atom, halogen atom or halogen-(C1-C6)-alkyl group; R3 represents hydrogen atom, halogen atom, (C1-C6)-alkyl group, hydroxyl group or (C1-C6)-alkoxy-group; t = 1; m = 0; each among X that can be similar or different represents (C2-C8)-alkyl group, hydroxy-(C1-C6)-alkyl group or (C3-C6)-cycloalkyl-(C1-C6)-alkyl group; n = 1 or 2. Invention provides the development of anilide derivative as insecticide, fungicide and acaricide against pests of agricultural and fruit crops.

EFFECT: valuable properties of compound.

5 cl, 6 tbl, 27 ex

 

The scope to which the invention relates.

The present invention relates to substituted anilinium derived; their intermediate compounds; chemicals for pest control agricultural and fruit crops, and in particular, to insecticides, fungicides or acaricides to control pests of agricultural and fruit crops containing these compounds as the active ingredient; and for the use of these chemical compounds.

Prior art

In JP-A-5-221994 and JP-A-10-251240 reported that compounds similar substituted anilides derivative of the present invention, can be used as a fungicide to protect agricultural and fruit crops.

The production of agricultural and horticultural crops and the like are still suffering serious damage caused by insect pests and the like, and therefore the development of new chemicals to control pests of agricultural and fruit crops, and in particular, insecticides for use in agriculture and horticulture, it is extremely necessary, for example, because of the emergence of insect pests that are resistant to existing chemicals. In addition, because of the increased among farmers, the elderly, etc. there is a need to develop a less time-consuming methodology the application and receipt of chemicals, which can be used to control pests of agricultural and horticultural crops and which have properties suitable for such methods of application.

Description of the invention

The authors of the present invention have conducted serious studies in order to develop new chemical compounds for pest control agricultural and fruit crops, and as a result of these studies it was found that substituted aniline derivative represented by the General formula (II) of the present invention, is new, is not described in the literature connection, which represents an intermediate compound that can be used for producing various derivatives having physiological activity, as a drug, agrochemical means or the like, and it was found that substituted aniline derivative of General formula (I)derived from the specified connection is a new connection that is not described in the literature and which can be used as a chemical means to control pests of agricultural and fruit crops, and in particular, as an insecticide, fungicide or acaricide against pests and fruit crops, and on the basis of these studies was to create the but the present invention.

Thus, the present invention relates to substituted anilides derivative represented by the General formula (I):

{where R1represents a hydrogen atom, (C1-C6)alkyl group, halogen(C1-C6)alkyl group, (C1-C6)alkylcarboxylic group, halogen(C1-C6)alkylcarboxylic group, phenyl group or substituted phenyl group having one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (these dialkylamino) (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;

R2represents a hydrogen atom, and the Ohm halogen or halo(C 1-C6)alkyl group;

R3represents a hydrogen atom, halogen atom, (C1-C6)alkyl group; a halogen(C1-C6)alkyl group; a cyano; hydroxyl group; and (C1-C6)alkoxygroup; halogen(C1-C6)alkoxygroup; and (C1-C6)alkoxy(C1-C3)alkoxygroup; halogen(C1-C6)alkoxy(C1-C3)alkoxygroup; and (C1-C6)alkylthio(C1-C3)alkoxygroup; halogen(C1-C6)alkylthio(C1-C3)alkoxygroup; and (C1-C6)alkylsulfonyl-(C1-C3)alkoxygroup; halogen(C1-C6)alkylsulfonyl(C1-C3)alkoxygroup; and (C1-C6)alkylsulfonyl(C1-C3)alkoxygroup; halogen(C1-C6)alkylsulfonyl(C1-C3)alkoxygroup; mono(C1-C6)alkylamino(C1-C3)alkoxygroup; di(C1-C6)alkylamino(C1-C3)alkoxygroup, where (C1-C6)alkyl groups may be the same or different; and (C1-C6)allylthiourea; halogen(C1-C6)alkylthio group; and (C1-C6)alkylsulfonyl group; halogen(C1-C6)alkylsulfonyl group; and (C1-C6)alkylsulfonyl group; halogen(C1-C6)alkyl is sulfonyloxy group; the amino group; a mono(C1-C6)alkylamino; di(C1-C6)alkylamino; where (C1-C6)alkyl groups may be the same or different; fenoxaprop; replaced fenoxaprop with one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups; phenylthiourea; replaced phenylthiourea with one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)al is exigrep, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups; phenylsulfinyl group; substituted phenylsulfinyl group having one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups mouthbut the same or different, and (C1-C6)alkoxycarbonyl groups; phenylsulfonyl group; substituted phenylsulfonyl group having one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups; phenyl(C1-C6)alkoxygroup; or substituted phenyl(C1-C6)alkoxygroup having on the ring one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)al is exigrep, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;

t is 0 or 1, m is an integer from 0 to 6,

if t is 0, then each of X, which may be the same or different, represents (C2-C8)alkyl group, (C1-C8)alkoxygroup, (C1-C6)allylthiourea, (C1-C6)alkylsulfonyl group, (C1-C6)alkylsulfonyl group, (C1-C6)alkoxy(C1-C6)alkyl group, a mono(C1-C6)alkylamino(C1-C6)alkyl group or di(C1-C6)alkylamino(C1-C6)alkyl group, where (C1-C6)alkyl groups specified di(C1-C6)alkylamino may be the same or different, and n is an integer from 1 to 4;

if t is equal to 1, each of X, which may be the same or different, represents and what Ohm halogen; the cyano; and (C1-C8)alkyl group; a halogen(C1-C8)alkyl group; a (C2-C8)alkenylphenol group; halogen(C2-C8)alkenylphenol group; and (C2-C8)alkylamino group; halogen(C2-C8)alkylamino group; and (C3-C6)cycloalkyl group; and (C3-C6)cycloalkyl(C1-C6)alkyl group; a (C1-C8)alkoxygroup; halogen(C1-C8)alkoxygroup; and (C1-C6)alkylthiols; and (C1-C6)alkylsulfonyl group; and (C1-C6)alkylsulfonyl group; a mono(C1-C6)alkylamino; di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different; and (C1-C8)alkylcarboxylic group; halogen(C1-C8)alkylcarboxylic group; and (C1-C8)alkylthiomethyl group; halogen(C1-C8)alkylthiomethyl group; and (C1-C6)alkylsulphonyl(C1-C6)alkyl group; a halogen(C1-C6)alkylsulphonyl(C1-C6)alkyl group; a (C1-C6)alkylthiomethyl(C1-C6)alkyl group; a halogen(C1-C6)alkylthiomethyl(C1-C6)alkyl group; a (C1-C6)alkoxy(C1-C6)Alki is inuu group; halogen(C1-C6)alkoxy(C1-C6)alkyl group; a (C1-C6)alkylthio(C1-C6)alkyl group; a (C1-C6)alkylsulfonyl(C1-C6)alkyl group; a (C1-C6)alkylsulfonyl(C1-C6)alkyl group; a mono(C1-C6)alkylamino(C1-C6)alkyl group; a di(C1-C6)alkylamino(C1-C6)alkyl group, where (C1-C6)alkyl groups specified di(C1-C6)alkylamino may be the same or different; a phenyl group; a substituted phenyl group having one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl group which can be the same or different, and (C1-C6)alkoxycarbonyl groups; fenoxaprop; replaced fenoxaprop with one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups; phenylthiourea; replaced phenylthiourea with one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio is p, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups; heterocyclic group; or a substituted heterocyclic group having one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups; and n is an integer from 1 to 4

1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups; and X, taken together with R1may form a 5-8-membered ring which may contain one or two atoms which may be the same or different and selected from oxygen atom, sulfur atom and nitrogen atom, between adjacent carbon atoms constituting the ring;

Z represents an oxygen atom or a sulfur atom, and

Q means the Deputy represented by any of formula Q1 - Q25:

(where each of the Y1that may be the same or different, represents a halogen atom; a cyano; a nitro-group; and (C1-C6)alkyl group; a halogen(C1-C6)alkyl group; a (C2-C6)alkenylphenol group; halogen(C2-C6)alkenylphenol group; and (C2-C6)alkylamino group; halogen(C2-C6)alkylamino group; and (C1-C6)alkoxygroup; halogen(C1-C6)alkoxygroup; and (C1-C6)allylthiourea; halogen(C1-C6)alkylthiols; and (C1-C6)alkylsulfonyl group; halogen(C1-C6)alkylsulfonyl group; and (C1-C6)alkylsulfonyl group; halogen(C1-C6)alkylsulfonyl group; a mono(C1-C6)alkylamino; di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different; a phenyl group; a substituted phenyl group having one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen 1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups; fenoxaprop; replaced fenoxaprop with one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups; heterocyclic group; or amestoy heterocyclic group, with one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;

in addition, two adjacent Y1on the aromatic ring, taken together, may form a condensed ring which may have one or more substituents, which may be the same or different and selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1 -C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;

Y2represents a halogen atom; a cyano; a nitro-group; and (C1-C6)alkyl group; a halogen(C1-C6)alkyl group; a (C1-C6)alkoxygroup; halogen(C1-C6)alkoxygroup; and (C1-C6)allylthiourea; halogen(C1-C6)alkylthiols; and (C1-C6)alkylsulfonyl group; halogen(C1-C6)alkylsulfonyl group; and (C1-C6)alkylsulfonyl group; halogen(C1-C6)alkylsulfonyl group; a mono(C1-C6)alkylamino; di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different; a phenyl group; a substituted phenyl group having one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl gr is PP, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups; fenoxaprop; replaced fenoxaprop with one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, the which (With 1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups; heterocyclic group; or a substituted heterocyclic group having one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;

Y3represents a hydrogen atom, (C1-C6)alkyl group, halogen(C1-C6)alkyl group, phenyl group or substituted phenyl group having one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, C 1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;

p represents an integer from 0 to 2, q represents an integer from 0 to 4, and r represents an integer from 0 to 3)},

to chemical means to control pests of agricultural and fruit crops, and to their use. In addition, the present invention relates to substituted aniline derivative represented by the General formula (II):

(where R1represents a hydrogen atom, (C1-C6)alkyl group, halogen(C1-C6)alkyl group, phenyl group or substituted phenyl group having one or more substituents, which may be the same or different and are selected and the atoms of halogen, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;

R2represents a hydrogen atom, a halogen atom or halogen(C1-C6)alkyl group;

R3represents a hydrogen atom, halogen atom, (C1-C6)alkyl group, halogen(C1-C6)alkyl group, a cyano, a hydroxyl group, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkoxy(C1-C6)alkoxygroup, halogen(C1-C6)alkoxy(C1-C6)alkoxygroup, (C1-C6)alkylthio(C1-C6)alkoxygroup, halogen(C1-C6)alkylthio(C1-C6)alkoxygroup, (C1-C6)alkyl is sulfinyl(C 1-C6)alkoxygroup, halogen(C1-C6)alkylsulfonyl(C1-C6)alkoxygroup, (C1-C6)alkylsulfonyl(C1-C6)alkoxygroup, halogen(C1-C6)alkylsulfonyl(C1-C6)alkoxygroup, mono(C1-C6)alkylamino(C1-C6)alkoxygroup, di(C1-C6)alkylamino(C1-C6)alkoxygroup, where (C1-C6)alkyl groups may be the same or different; and (C1-C6)allylthiourea; halogen(C1-C6)alkylthio group; and (C1-C6)alkylsulfonyl group, halogen(C1-C6)alkylsulfonyl group; and (C1-C6)alkylsulfonyl group; halogen(C1-C6)alkylsulfonyl group; amino group; mono(C1-C6)alkylamino; di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different; fenoxaprop; replaced fenoxaprop with one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio is, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups; phenylthiourea; replaced phenylthiourea with one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups; phenylsulfinyl the ing group; substituted phenylsulfinyl group having one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups; phenylsulfonyl group; substituted phenylsulfonyl group having one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkyl is whinily groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups; phenyl(C1-C6)alkoxygroup; or substituted phenyl(C1-C6)alkoxygroup having on the ring one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups;

t is 1, and m is an integer from 0 to 6,

each X, which may be the same or different, represents a halogen atom, a cyano; and (C1-C8)alkyl group; a halogen(C1-C8)alkyl group; a (C2-C8)alkenylphenol group; halogen(C2-C8)alkenylphenol group; and (C2-C8)alkylamino group; halogen(C2-C8)alkylamino group; and (C3-C6)cycloalkyl group; and (C3-C6)cycloalkyl(C1-C6)alkyl group; a (C1-C8)alkoxygroup; halogen(C1-C8)alkoxygroup; and (C1-C6)alkylthiols; and (C1-C6)alkylsulfonyl group; and (C1-C6)alkylsulfonyl group; a mono(C1-C6)alkylamino; di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different; and (C1-C6)alkylsulphonyl(C1-C6)alkyl group; a halogen(C1-C6)alkylsulphonyl(C1-C6)alkyl group; a (C1-C6)alkylthiomethyl(C1-C6)alkyl group; a (C1-C6)alkoxy(C1-C6)alkyl group; a halogen(C1-C6)alkoxy(C1-C6)alkyl group; a (C1-C6)alkylthio(C1-C6)alkyl group; a (C1-C6)alkylsulfonyl(C1- 6)alkyl group; a (C1-C6)alkylsulfonyl(C1-C6)alkyl group; a mono(C1-C6)alkylamino(C1-C6)alkyl group; a di(C1-C6)alkylamino(C1-C6)alkyl group, where (C1-C6)alkyl groups specified di(C1-C6)alkylamino may be the same or different; a phenyl group; or a substituted phenyl group having one or more substituents, which may be the same or different and are selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups; and n is an integer from 1 to 4

in addition, two adjacent X on the aromatic ring, taken together,may form a condensed ring, which may have one or more substituents, which may be the same or different and selected from halogen atoms, ceanography, nitro, (C1-C6)alkyl groups, halogen(C1-C6)alkyl groups, (C1-C6)alkoxygroup, halogen(C1-C6)alkoxygroup, (C1-C6)alkylthio, halogen(C1-C6)alkylthio, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, (C1-C6)alkylsulfonyl groups, halogen(C1-C6)alkylsulfonyl groups, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, in which (C1-C6)alkyl groups may be the same or different, and (C1-C6)alkoxycarbonyl groups), which is an intermediate compound used to obtain the substituted anilides derived.

The method of implementation of the present invention

In the definition of General formula (I)presented for substituted anilides derivative of the present invention, the term "halogen atom" means a chlorine atom, bromine atom, iodine atom or fluorine atom. In this definition, the prefix "n-" means "normal", the prefix "s-" means "secondary", the prefix "t" means tertiary," and the prefix "i-" Osnach is no "best". The term "(1-C6)alkyl" means a straight or branched alkyl group having from 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl or the like, the Term "halogen(C1-C6)alkyl" means and substituted straight or branched alkyl group with 1 to 6 carbon atoms having as the substituent(s) one or more halogen atoms, which may be the same or different. The term "(3-C6)cycloalkyl" means a cyclic alkyl group with 3-6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or the like

The term "heterocyclic group" means a 5 - or 6-membered heterocyclic group having one or more heteroatoms selected from oxygen atom, sulfur atom and nitrogen atom. Such a heterocyclic group is, for example, Peregrina group, a pyridine-N-oxide group, pyrimidinyl group, furilla group, tetrahydrofuryl group, thienyl group, tetrahydroquinoline group, tetrahydropyranyl group, tetrahydropyranyl group, oxazoline group, isoxazolyl group, oxadiazolyl group, thiazolidine group, isothiazolinone group, thiadiazolyl group, imidazolidinyl group, thiazolidine group and the feast is zailina group. The term "condensed ring" means, for example, naphthalene, tetrahydronaphthalene, inden, indan, quinoline, hinzelin, indole, indoline, chroman, isochroman, benzodioxan, benzodioxole, benzofuran, dihydrobenzofuran, benzothiophene, dihydrobenzofuran, benzoxazole, benzothiazole, benzimidazole and indazole.

In some cases, substituted aniline derivative of General formula (I) of the present invention contains in its structural formula one or more asymmetric centers, and in some cases it has two or more optical isomers and diastereomers. The present invention also includes all of the individual optical isomers and a mixture of these isomers in any ratio. Substituted aniline derivative of General formula (I) of the present invention in some cases has two geometric isomer, due to the presence of carbon-carbon double bond in its structural formula. The present invention also includes individual geometrical isomers and mixture of these isomers in any proportion.

In substituted anilide derivative of General formula (I) of the present invention, Q is preferably Q9, Q14 and Q15, and more preferably Q9; Y1preferably represents a halogen atom or (C1-C2)alkyl group, and particularly preferably 3,Demetriou group; Y3preferably represents (C1-C3)alkyl group or phenyl group, and particularly preferably a methyl group; Xnpreferably represents (C5-C7)alkyl group in the 2-position, particularly preferably6the alkyl group in the 2-position; Z especially preferably represents an oxygen atom; R1especially preferably represents a hydrogen atom; R2especially preferably represents triptorelin group; R3preferably represents a hydrogen atom, halogen atom or (C1-C2)alkoxygroup, and especially preferably a hydrogen atom; m is particularly preferably equal to 0, and t is particularly preferably equal to 1.

Typical methods of obtaining anilides derivative represented by the General formula (I) of the present invention, described below, but these methods should not be construed as limiting the scope of the invention.

The method of obtaining 1.

where R1, R2, R3, X, m, n, t and Q are defined above, R4represents a hydrogen atom, (C1-C6)alkyl group, halogen(C1-C6)alkyl group, phenyl group, substituted phenyl group or phenyl(C1-C6)alkyl group, and W represents-O-, -S -, or N(R4)-, where R defined above.

Substituted aniline derivative (I-3), that is substituted aniline derivative of General formula (I), where Z is Oh, can be obtained by the reaction of interaction of aniline derivative having any one of General formulas (II-1) to (II-3) with the acid chloride of heterocyclic carboxylic acids of General formula (III) in an inert solvent in the presence or in the absence of a base, or by reaction of interaction of aniline derivative having any one of General formulas (II-1) to (II-3) with a heterocyclic carboxylic acid of General formula (IV) in an inert solvent in the presence of a condensing agent and in the presence or in the absence of base. This may be carried out in a standard way obtain amide.

Aniline derivative of General formula (II-2) can be obtained by restoring the aniline derivative of General formula (II-1) in an inert solvent in the presence of a reducing agent.

Aniline derivative of General formula (II-3) can be obtained by the reaction of interaction of aniline derivative of General formula (II-1) with an alcohol derived from a thiol derivative or a derivative of an amine of General formula (V) in an inert solvent in the presence or absence of a base.

General formula (II-1) → General formula (II-2)

Reducing agent (restoring the m-agent), used in this reaction are, for example, metal hydrides such as alumalite lithium, borohydride lithium, borohydride sodium hydride diisobutylamine, bis(2-methoxyethoxy)alumoweld sodium and the like; or a metal or metal salts, such as lithium metal, etc. with regard to the quantity of the reducing agent, the reducing agent may be used in an appropriate amount selected in the range from 1 equivalent to an excess of one equivalent of aniline derivative of General formula (II-1).

As for the inert solvent used in this reaction, this reaction can be used any inert solvent, provided that it has no significant inhibitory effect on the course of the reaction. As an example, an inert solvent can be mentioned, for example, aromatic hydrocarbons such as benzene, toluene, xylene and the like; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride and the like; halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene and the like; acyclic or cyclic ethers, such as diethyl ether, dioxane, tetrahydrofuran, etc. These inert solvents can be used alone or as mixtures.

As for the reaction temperature, the reaction mo is et to be carried out in the range from room temperature to the boiling point of the used inert solvent. Although the reaction time may vary depending on the scale of the reaction, the reaction temperature and the like, however, this reaction can be carried out during the period of time from several minutes to 50 hours.

After completion of the reaction, the desired compound is recovered from the reaction system containing such a compound, the standard method and, if necessary, purified by recrystallization, column chromatography and the like, which may be obtained the desired connection. This connection can be used in the next stage of the reaction without isolation from the reaction medium.

General formula (II-1) → General formula (II-3)

The base used in this reaction are, for example, metal hydrides such as lithium hydride, sodium hydride, potassium hydride and the like; metal alcoholate such as sodium methoxide, ethoxide sodium tert-piperonyl potassium and the like; and altimetry, such as n-utility, second-utility, tert-utility, etc. with regard to the amount used of the base, this base can be used in an appropriate amount selected in the range from 1 equivalent to an excess of one equivalent of aniline derivative of General formula (II-1).

As for the inert solvent used in this reaction, there may be used any inert dissolve the l provided that he has no significant inhibitory effect on the course of the reaction. As an example, an inert solvent can be mentioned, for example, aromatic hydrocarbons such as benzene, toluene, xylene and the like; alcohols such as methanol, ethanol and the like; acyclic or cyclic ethers, such as diethyl ether, 1,2-dimethoxyethane, dioxane, tetrahydrofuran, etc. These inert solvents can be used alone or as mixtures.

As for the reaction temperature, this reaction can be carried out in the range from -70°C to the boiling point of the used inert solvent. Although the reaction time may vary depending on the scale of the reaction, the reaction temperature and the like, however, this reaction can be carried out during the period of time from several minutes to 50 hours.

After completion of the reaction, the desired compound is recovered from the reaction system containing the desired connection, the standard method and, if necessary, purified by recrystallization, column chromatography and the like, which may be obtained the desired connection. This connection can be used in the next reaction stage without isolation from the reaction medium.

General formula (II-1), General formula (II-2) or

General formula (II-3) → General formula (I-3)

To danceroom agent, used in this reaction are, for example, diethylthiophosphate (DEPC), carbonyl-diimidazole (CDI), 1,3-DICYCLOHEXYL-carbodiimide (DCC), esters harpalinae acid and iodide 2-chloro-1-methylpyridine.

As the base used in this reaction can be used, for example, inorganic or organic bases. Inorganic bases are, for example, hydroxides of alkali metal atoms such as sodium hydroxide, potassium hydroxide and the like; hydrides of alkali metals, sodium hydride, potassium hydride and the like; alkali metal salts and alcohols, such as ethoxide sodium tert-piperonyl potassium and the like; carbonates such as sodium carbonate, potassium carbonate, sodium bicarbonate, and the like, Organic bases are, for example, triethylamine, pyridine and DBU. The amount used of the base, this base can be used in an appropriate amount selected in the range from 1 mol to molar excess per mole of the derivative of heterocyclic carboxylic acids of General formula IV.

As for the inert solvent used in this reaction, there may be used any inert solvent, provided that it has no significant inhibitory effect on the course of the reaction. As an example, an inert solvent can be mentioned, for example aromatic hydrocarbons, such as benzene, toluene, xylene and the like; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride and the like; halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene and the like; acyclic or cyclic ethers, such as diethyl ether, dioxane, tetrahydrofuran and the like; esters such as ethyl acetate and the like; amides, such as dimethylformamide, dimethylacetamide and the like; dimethyl sulfoxide; 1,3-dimethyl-2-imidazolidinone; acetone; methyl ethyl ketone; and the like, These inert solvents can be used alone or as mixtures.

Since this reaction is equimolar, it is sufficient that these reagents were used in equimolar quantities, although any of these reagents may be used in excess. As for the reaction temperature, this reaction can be carried out in the range from room temperature to the boiling point of the used inert solvent. Although the reaction time may vary depending on the scale of the reaction, the reaction temperature and the like, however, this reaction can be carried out during the period of time from several minutes to 48 hours.

After completion of the reaction, the desired compound is recovered from the reaction system containing this connection, the standard method and, if necessary, clean the by recrystallization, column chromatography and the like, which may be obtained the desired connection.

Aniline derivative compounds of General formula (II-1), i.e. the parent compound in this reaction can be obtained by a method described in JP-A-11-302233 or JP-A-2001-122836.

The method of obtaining 2.

where R1, R2, R3, X, m, n, t and Q are defined above.

Substituted aniline derivative (I-4), that is substituted aniline derivative of General formula (I), where Z is S, can be obtained by the reaction of interaction of substituted anilides derivative of General formula (I-3) with a reagent of Lawesson in accordance with a well-known method (Tetrahedron Lett., 21(42), 4061 (1980)).

Typical compounds used as substituted anilides derivative of General formula (I)are listed in tables 1-4, and the typical compounds used as the substituted aniline derivative of General formula (II)are listed in table 6, but they should not be construed as limiting the scope of the present invention. In tables 1-4 and in table 6 physical property means melting point (° (C) or refractive index (the value in brackets indicates the temperature (°)), and "Me" means methyl group, "Et" means ethyl group, "Pr" means through the group, "Bu" means a bout the optimum group, and "Ph" means phenyl group.

Table 1 (continued)
No.XnY3mR3Physical property
1-382-CH(Me)CH2Snme23-ClMe0H
1-392-CH(Me)CH2Snme23-BrMe0H1.5111(22.2)
1-402-CH(Me)CH2CHMe23-IMe0Hamorphous
1-412-CH(Me)CH2CHMe23-SMeMe0H129-130
1-422-CH(Me)CH2CHMe23-SOMeMe0H
1-432-CH(Me)CH2CHMe23-SO2MeMe0H
1-442-CH(Me)CH2CHMe23-OMe Me0H102-105
1-452-CH(Me)CH2Snme25-IUMe0H1.4790(25.2)
1-462-CH(Me)CH2CHMe25-SMeMe0H1.6201(16.8)
1-472-CH(Me)CH2Snme25-SOMeMe0H1.4930(23.7)
1-482-CH(Me)CH2CHMe25-SO2MeMe0H48
1-492-CH(Me)CH2Snme25-FMe0H
1-502-CH(Me)CH2Snme25-ClMe0Hpasta
1-512-CH(Me)CH2Snme25-ClEt0H1.5110(21.7)
1-522-CH(Me)CH2Snme25-ClCH2CH2F0H1.4931(22.5)
1-532-CH(Me)CH2Snme2 5-BrMe0Hpasta
1-542-CH(Me)CH2Snme25-BrEt0H1.5061
1-552-CH(Me)CH2Snme25-Brt-Bu0H67-68
1-562-CH(Me)CH2CHMe25-IMe0H119-120
1-572-CH(Me)CH2CHMe25-IEt0H132-133
1-582-CH(Me)CH2CHMe25-It-Bu0H98-99
1-592-CH(Me)CH2CHMe25-IPh0H127-128
1-602-CH(Me)CH2CHMe23-Cl-5-MeMe0H95-97

Table 1 (continued)
No.XnY3mR3NAT the static property
1-612-N(Me)CH2Snme23-Br-5-IUMe0H1.5208(21.1)
1-622-N(Me)CH2Snme23-I-5-IUMe0H1.5252(21.1)
1-632-N(Me)CH2Snme23-I-5-IUEt0H170-171
1-642-N(Me)CH2Snme23-Me-5-FMe0F
1-652-N(Me)CH2Snme23-Me-5-FMe0H1.4974(22.8)
1-662-N(Me)CH2Snme23-Me-5-FMe0OMe1.4889(21,2)
1-672-N(Me)CH2Snme23-Me-5-FMe1F
1-682-N(Me)CH2Snme23-Me-5-FMe1H
1-692-N(Me)CH2Snme23-Me-5-FMe1OMe
1-702-N(Me)CH2Snme23-Me-5-ClMe0F88-90
1-712-N(Me)CH2Snme23-Me-5-ClMe0H1.5025(23.7)
1-722-N(Me)CH2Snme23-Me-5-ClMe0OMeamorphous
1-732-N(Me)CH2Snme23-Me-5-ClMe0OEt1.5003(15.7)
1-742-N(Me)CH2Snme23-Me-5-ClMe1F
1-752-N(Me)CH2Snme23-Me-5-ClMe1H
1-762-N(Me)CH2Snme23-Me-5-ClMe1OMe
1-772-N(Me)CH2Snme23-Me-5-ClMe1OEt
1-782-N(Me)CH2Snme23-Me-5-ClEt01.4905(21.2)
1-792-N(Me)CH2Snme23-Me-5-ClEt0OMe
1-802-N(Me)CH2Snme23-Me-5-ClEt0OEt
1-812-N(Me)CH2Snme23-Me-5-BrMe0H134-135
1-822-N(Me)CH2Snme23-Me-5-BrMe0OMe96-97
1-832-N(Me)CH2Snme23-Me-5-BrEt0OH1.5140(22.2)

Table 1 (continued)
No.XnY3mR3Physical property
1-1042-N(Me)CH2Snme23-CF3-5-ClMe0OMe1.4712(18.2)
1-1052-N(Me)CH2Snme23-CFsub> 3-5-OPhMe0N1.4951(19.4)
1-1062-N(Me)CH2Snme23,5-Me2Me0F81-82
1-1072-N(Me)CH2Snme23,5-Me2Me0N1.4958(15.7)
1-1082-N(Me)CH2Snme23,5-Me2Me0OMe94-96
1-1092-N(Me)CH2Snme23,5-Me2Me0OEt1.4958(20.1)
1-1102-N(Me)CH2Snme23,5-Me2Me1F
1-1112-N(Me)CH2Snme23,5-Me2Me1N
1-1122-N(Me)CH2Snme23,5-Me2Me1QMe
1-1132-N(Me)CH2Snme23,5-Me2Me1OEt
1-1142-N(Me)CH2Snme23,5-Me2Et0F1.4950(18.4)
1-1152-N(Me)CH2Snme23,5-Me2Et0H
1-1162-N(Me)CH2Snme23,5-Me2Et0OMe1.4961(27,8)
1-1172-N(Me)CH2Snme23,5-Me2Et0OEt
1-1182-N(Me)CH2Snme23,5-Me2n-Pr0F1.4907(19.2)
1-1192-N(Me)CH2Snme23,5-Me2n-Pr0H1.4970(17.4)
1-1202-N(Me)CH2Snme23,5-Me2n-Pr0OMe
1-1212-N(Me)CH2Snme23,5-Me2n-Pr0OEt
1-1222-N(Me)CH2Snme23,5-Me20F
1-1232-N(Me)CH2Snme23,5-Me2Ph0H
1-1242-N(Me)CH2Snme23,5-Me2Ph0OMe
1-1252-N(Me)CH2Snme23,5-Me2Ph0OEt
1-1262-N(Me)CH2Snme2the 3.5-F2Me0F

1,4904(25,0) Me
Table 1 (continued)
NoXnY3mR3Physical property
1-1652-CH(Me)CH2CME2-3-IU3,5-Me2Me0H1,4863(25,0)
1-1662-CH(Me)CH2CME2-3-IU3,5-Me2Me0F
1-1672-CH(Me)CH2CMe2O-33,5-Me2Me0H189-193
1-1682-CH(Me)CH2CME2-33,5-Me2Me0H199-200
1-1692-CH(Me)CH2Snme23,5-Me22,6-0H193-195
Cl2-4-
CF3-Ph
1-1702-CH(Me)CH2Snme25-CF3Me0H143-145
1-1712-CH(Me)CH2CHMe23-CF3-5-IUMe0H1,4810(22,5)
1-1722-CH(Me)CH2Snme25-OMeMe0H1,5015(21,0)
1-1732-CH(Me)CH2CHMe23-och2CH=CH2,0H1,5262(21,1)
5-OPh
1-1742-CH(Me)CH2-Snme23-CF3-5-BrMe0H145-146
1-1752-CH(Me)CH2Snme23-CF3-5-IMe0H171-173
1-1762-CH(Me)CH2Snme23-Me-5-CF3Me0H42-45
1-1772-CH(Me)CH2CHEt23,5-Me2Me0H1,4951(25,7)
1-1782-CH(Me)CH2with Neh3,5-Me2Me0H1,5020(25,4)
1-1792-CH(Me)CH2-with-Bu3,5-Me2Me0H1,4828(27,9)
1-1802-CH(OH)(Me)CH2-Snme23,5-Me2Me0F186-187
1-1812-CH(OH)(Me)CH2 23,5-Me2Me0H172-173

NoXnY3mR3Physical property
1-1822-CH(Et)CH2CHMe23,5-Me2Me0N103-104
1-1832-CH(Et)CHzCHMe23-Me-5-ClMe0N95-96
1-1842-CH(n-Pr)CH2CHMe23-Me-5-ClMe0N1,4965(26,2)
1-1852-CH(Me)CH2Snme23,5-Et2Me0N1,4694(26,4)
1-186 2-CH(Me)CH2Snme23,5-Me2ClCH2CH20Noil
1-1872-CH(Me)CH2CHMe23,5-Me2CF3CH20Noil
1-1882-CH(Me)CH2Snme23,5-Me2ONSN2CH20Noil
1-1892-CH(Me)CH2Snme2, 6-Me3,5-Me2Me0Namorphous
1-1902-CH(Me)CH2Snme2A 6-IU3-IUMe0Namorphous
1-1912-CH(Me)CH2Snme23,5-Me2CHF20 N1,4879(28,8)
1-1922-CH(Me)CH2Snme23,5-Me2FCH2CH20N1,4747(25,1)
1-1932-CH(Me)CH2CHMe23,5-Me2CH2=SN0N1,5084(18,7)
1-1942-CH(Me)CH2CHMe23,5-Me2N0Npasta
1-1952-CH(Me)CH2Snme23-CF3-5-FMe0N1,4624(25,4)
1-1962-CH(Me)CH2Snme23-CF3-5-IUMe0N1,4711(21,2)
1-1972-CH(Me)CH2Snme23-Me-5-CF Me0N1,4700(21,2)
Table 1-1 (Q=Q9, R2=CF3, Z=0, t=1)
NoXnY3mR1R3Physical property
1-1982-CH(Me)CH2CHMe23,5-Me2Me0EtFMC(m/z):
492,491,
406,281,
207,138,
137,43

td align="center"> 3-17
Table 3 (R1=H, R2=CF3, Z=O, m=0, t=1)
No.QXnR3Physical property
3-1Q12-CH(Me)CH2CHMe23-CF3N
3-2Q12-CH(Me)CH2Snme23,5-Cl2N108-109
3-3Q22-CH(Me)CH2Snme24-CF3N1.4860(22.7)
3-4Q22-CH(Me)CH2Snme22-ClN68
3-5Q22-CH(Me)CH2Snme22-Cl-6-MeNamorphous
3-6Q32-CH(Me)CH2Snme23-CF3N
3-7Q3 2-CH(Me)CH2Snme22,6-Cl2N1.5182(20.5)
3-8Q62-CH(Me)CH2Snme22-SMe-4-CF3Npasta
3-9Q62-CH(Me)CH2Snme24-CF3N
3-10Q112-CH(Me)CH2Snme2MeF104
3-11Q112-CH(Me)CH2Snme2MeNamorphous
3-12Q112-CH(Me)CH2CHMe2CF3N85-88
3-13Q122-CH(Me)CH2Snme22,4-Me2N72-73
3-14Q122-CH(Me)CH2Snme22,4-Me2OMe
3-15Q132-CH(Me)CH2Snme23-BrF
3-16Q132-CH(Me)CH2Snme23-BrN
Q132-CH(Me)CH2Snme23-BrOMe
3-18Q142-CH(Me)CH2Snme22-BrN

Table 3 (continued)
No.QXnR3Physical property
3-19Q142-CH(Me)CH2CHMe22-BrOMe
3-20Q142-CH(Me)CH2CHMe22-BrOEt
3-21Q142-CH(Me)CH2Snme24-BrN1.5080(20.4)
3-22Q142-CH(Me)CH2CHMe24-BrCME
3-23Q142-CH(Me)CH2CHMe24-BrOEt
3-24Q142-CH(Me)CH2CHMe22,4-Me2N
3-25 Q142-CH(Me)CH2CHMe22,4-Me2OMe
3-26Q142-CH(Me)CH2CHMe22,4-Me2OEt
3-27Q152-CH(Me)CH2CHMe2NN133.5-135
3-28Q152-CH(Me)CH2CHMe23-ClNpasta
3-29Q152-CH(Me)CH2CHMe23-BrN
3-30Q152-CH(Me)CH2CHMe23-IN1.5365(18.4)
3-31Q152-CH(Me)CH2CHMe23-IOMe1.5081(18.5)
3-32Q182-CH(Me)CH2CHMe22-ClN104.5-106
3-33Q182-CH(Me)CH2CHMe22-Me-5-(2-Cl-Ph)N1.5425(21.1)
3-34Q212-CH(Me)CH2CHMe23,5-Me2Namorphous
3-35Q21 2-CH(Me)CH2CHMe23,5-Me2OMe1.4870(19.4)
3-36Q242-CH(Me)CH2CHMe23,5-Me2N
3-37Q242-CH(Me)CH2CHMe23,5-Me2OMe

Table 3 (continued)
NoQXnR3Physical property
3-38Q22-CH(Me)CH2CHMe22-MeH63-65
3-39Q22-CH(Me)CH2CHMe26-MeH1,4845(23,2)
3-40Q22-CH(Me)CH2CHMe22,6-Me2H80-82
3-41Q22-CH(Me)CH2CHMe22-Me-6-CF3H1,4690(21,4)
3-42Q22-CH(Me)CH2CHMe24-MeH1,4961(22,2)
3-43Q2 2-CH(Me)CH2CHMe22-CF3H140
3-44Q62-CH(Me)CH2CHMe24-MeH107-110
3-45Q112-CH(Me)CH2CHMe2t-BuHpasta
3-46Q112-CH(Me)CH2CHMe2c-PrH1,5117(25,0)
3-47Q122-CH(Me)CH2CHMe22-MeH1,4965(27,5)
3-48Q122-CH(Me)CH2CHMe23,5-Me2H1,4895(21,0)
3-49Q152-CH(Me)CH2CHMe25-MeH128-130
3-50Q152-CH(Me)CH2CHMe23-MeH92-94
3-51Q192-CH(Me)CH2CHMe24-MeH1,5005(20,0)
3-52Q192-CH(Me)CH2CHMe22-ClH106-107
3-53Q192-CH(Me)CH2CHMe22,4-Mesub> 2H1,5157(20,0)
3-54Q192-CH(Me)CH2CHMe22-Me-4-i-PrH1,5248(23,5)
3-55Q192-CH(Me)CH2CHMe22-Me-4-EtH1,4056(28,0)
3-56Q192-CH(Me)CH2CHMe22-Et-4-MeH1,5160(23,5)
3-57Q232-CH(Me)CH2CHMe22,4-Cl2H1,5049(20,9)
358 forQ232-CH(Me)CH2CHMe23-MeH55-56

Q17
Table 4 (R1=H, R2=CF3, Z=O, m=0, t=1)
No.QXnY3R3Physical property
4-1Q82-CH(Me)CH2CHMe24-Cl-5-IUMeH160
4-2Q82-CH(Me)CH2CHMe24-Br-5-IUMeH149-150
4-3 Q102-CH(Me)CH2CHMe23-IUMeH1.4848(23.6)
4-4Q102-CH(Me)CH2CHMe23-me-4-ClMeH108-109
4-5Q102-CH(Me)CH2CHMe23-Me-4-BrMeH112-113
4-6Q102-CH(Me)CH2CHMe23-t-Bu-4-ClMeH1.4915(23.9)
4-7Q102-CH(Me)CH2CHMe23-Me-4-NO2MeH1.4971(25.3)
4-8Q162-CH(Me)CH2CHMe22,4-Me2MeF
4-9Q162-CH(Me)CH2CHMe22,4-Me2MeH1.5062(18.4)
4-10Q162-CH(Me)CH2CHMe22,4-Me2MeOMe
4-11Q162-CH(Me)CH2CHMe22,4-Me2MeOEt
4-12Q162-CH(Me)CH2CHMe22,4-Me2EtF
4-13Q162-CH(Me)CH2CHMe22,4-Me2EtH
4-14Q162-CH(Me)CH2CHMe22,4-Me2EtOMe
4-15Q162-CH(Me)CH2CHMe22,4-Me2EtOEt
4-16Q172-CH(Me)CH2CHMe23-IUMeF
4-17Q172-CH(Me)CH2CHMe23-IUMeH
4-18Q172-CH(Me)CH2CHMe23-IUMeOMe
4-19Q172-CH(Me)CH2CHMe23-IUMeOEt
4-20Q172-CH(Me)CH2CHMe23-ClEtF
4-212-CH(Me)CH2CHMe23-ClEtH
4-22Q172-CH(Me)CH2CHMe23-ClEtOMe
4-23Q172-CH(Me)CH2CHMe23-ClEtOEt

Table 4 (continued)
NoQXnY2R3Physical property
4-24Q82-CH(Me)CH2CHMe25-MeMeH142-143
4-25Q82-CH(Me)CH2CHMe25-MeCHF2H1,4841(22,3)
4-26Q82-CH(Me)CH2CHMe24,5-Me2MeH111-112
4-27Q82-CH(Me)CH2CHMe25-Me2-Cl-H1,5231(26,6)
Ph
4-28Q102-CH(Me)CH2CHMe23,4-Me2MeH1,4919(28,2)
4-29Q102-CH(Me)CH2CHMe23-(CH2)3-4MeH1,5179(22,5)
4-30Q162-CH(Me)CH2CHMe24-MeHH78-80
4-31Q162-CH(Me)CH2CHMe24-MeMeH90-92
4-32Q172-CH(Me)CH2CHMe2nMeH84-87

Table 5 presents data1H-NMR for compounds having physical properties defined by the term "amorphous" in tables 1-4.

Table 5
No.1H-NMR [CDC13/TMS, the value of δ (ppm)]
1-40to 8.20 (s, 1H), 7,98 (s, 1H), of 7.90 (d, 1H), 7,32-7,25 (m, 2H), of 4.05 (m, 1H), 3.96 points (s, 3H), 3,20 (m, 1H), 1,65-of 1.40 (m, 3H), of 1.24 (d, 3H), from 0.84 (m, 6H)
1-72of 8.04 (d, 1H), 7,87 (s, 1H), 7,46-7,39 (m, 2H), 3,86 (s, 3H), 3,47 (s, 3H), 3,03 (m, 3H), and 52 (C, 3H), 1,69-of 1.40 (m, 3H), of 1.23 (d, 3H), from 0.84 (d, 6H)
1-868,01 (d, 1H), 7,83 (s, 1H), 7,47-7,39 (m, 2H), 3,91 (s, 3H), 3,47 (s, 3H), of 3.07 (m, 1H), equal to 2.94 (m, 1H), 1,67-of 1.40 (m, 3H), 1.30 and of 1.20 (m, 6H), is 0.84 (d, 6H)
1-1327,98 (d, 1H), 7,83 (s, 1H), 7,30-7,21 (m, 2H), Android 4.04 (m, 1H), a 3.87 (s, 3H), 3,10-2,80 (m, 3H), 1,63-of 1.40 (m, 3H), 1,33-of 1.18 (m, 6H), is 0.84 (d, 6H)
1-1488,13 (d, 1H), 7,50-7,40 (m, 2H), 7,33 (s, 1H), of 3.77 (s, 3H), 2,82 (m, 1H), 2,54 (s, 3H), of 2.51 (s, 3H), 1,72-of 1.52 (m, 2H), 1,52-of 1.39 (m, 1H), 1.27mm (d, 3H), 1,21-1,10 (m, 1H), 1,10-of 0.91 (m, 1H), of 0.82 (d, 6H)
3-58,32 (s, 1H), to 8.20 (d, 1H), 8,01 (d, 1H), 7,35-7,20 (m, 3H), 4,06 (m, 1H), 3,05 (m, 1H), 2,61 (s, 3H), 1.60-to of 1.40 (m, 3H), 1,22 (d, 3H), from 0.84 (d, 6H)
3-34the 7.85 (d, 1H), 7,31-7,20 (m, 3H), 4,06 (m, 1H), 2,92 (m, 1H), to 2.67 (s, 3H), of 2.51 (s, 3H), 1.60-to of 1.40 (m, 3H), 1,22 (t, 3H), of 0.85 (m, 6H)

General formula (II)

Table 6 (R1=N, t=1)
No.XnmR2R31H-NMR [CDCl3/TMS, the value of δ (ppm)]
5-12-n-Pr0CF3H7,12-7,02 (m, 2H), 6,69 (d, 1H), 4,0 to 3.7 (m, 3H), 2,52 (square, 2H), 1.27mm (t, 3H)
5-22-t-Bu0CF3H7,17 (s, 1H), 7,06 (d, 1H), only 6.64 (d, 1H), 4,1-3,9 (user., 2H), 3,91 (m, 1H), 141 (C, 9H)
5-32-Ph0CF3H7,52-to 7.32 (m, 5H), 7,19-7,10 (m, 2H), 6,77 (d, 1H), 4,08-of 3.85 (m, 3H)
5-42-CH(Me)

CHMe2
0CF3H7,08-7,01 (m, 2H), of 6.71 (s, 1H), 3,91 (m, 1H), 2,50 (m, 1H), 1,87 (m, 1H), 1,21 (d, 3H), of 0.92 (d, 3H), of 0.87 (d, 3H)
5-52-CH(Me)

CHMe2-6-Et
0CF3Hof 6.96 (d, 2H), 3,92 (m, 1H), 3,85-3,70 (user., 2H), 2,65 (m, 1H), 2,53 (DD, 2H), 1,80 of 1.50 (m, 2H), of 1.23 (d, 3H), of 0.90 (t, 3H)
5-62-(CH2)4-30CF3Hfrom 7.24 (d, 1H), 6,60 (d, 1H), to 4.41 (m, 1H), 3,76 (user., 2H), 2,70 (user., 2H), 2,47 (user., 2H), of 1.84 (m, 4H)
5-72-CH=CH-CH

=CH-3
0CF3Hto $ 7.91-to 7.84 (m, 2H), 7, 68-7,47 (m, 3H), PC 6.82 (d, 1H), 4,96 (m, 1H), 4,40-4,20 (user., 2H)
5-82-CH(Me)

CH2CH3
0CF3H7,06-6,98 (m, 2H), to 6.67 (d, 1H), 3,91 (m, 1H), 3,85-3,70 (user., 2H), 2,62 (m, 1H), 1,78 of 1.50 (m, 2H), 1,22 (d, 3H), of 0.89 (t, 3H)
5-92-CH(Me)

CH2CH2CH3
0CF3H7,08-7,00 (m, 2H), is 6.61 (d, 1H), 3,91 (m, 1H), 3,82-3,70 (user., 2H), 2,71 (m, 1H), 1.70 to 1,50 (m, 2H), 1,40-1,20 (who, 5H), of 0.90 (t, 3H)
5-102-CH(Me)

CH2CH2CH3
0CF3OMefrom 7.24 (s, 1H), 7,16 (d, 1H), 6,70 (d, 1H), 4,00-3,82 (user., 2H), 3.43 points (s, 3H), 2,73 (m, 1H), 1.70 to a 1.45 (m, 2H), 1,40-1,20 (m, 5H), of 0.90 (t, 3H)
5-112-CH(Me)

CH2CHMe2
0CF3H7,10-7,00 (m, 2H), 6,69 (s, 1H), 3,91 (m, 1H), 2,80 (m, 1H), 1,65 of 1.50 (m, 2H), 1,43-1,32 (m, 1H), 1,21 (d, 3H), of 0.89 (t, 6H)
5-122-CH(Me)

CH2CHMe2
0CF3OH7,39 (s, 1H), 7,30 (d, 1H), of 6.68 (d, 1H), 3,90-3,60 (user., 2H), and 2.79 (m, 1H), 1,61 of 1.50 (m, 1H), 1,45-of 1.35 (m, 1H), 1,21 (d, 3H), 0,89 (square, 6H)
5-132-CH(Me)

CH2CHMe2
0CF3OMe7,26 (s, 1H), 7,15 (d, 1H), 6,70 (d, 1H), 4,00-3,65 (user., 2H), 3.43 points (s, 1H), and 2.79 (m, 1H), and 1.56 (m, 2H), 1,37 (m, 1H), 1,20 (d, 3H), of 0.91 (t, 6H)
5-142-CH(Me)CH2CHMe20CF3OEt7,26 (s, 1H), 7,16 (d, 1H), 6,69 (d, 1H), 3,98-3,67 (user., 2H), 3,59 (square, 2H), 2,80 (m, 1H), and 1.56 (m, 2H), 1,38 (m, 1H), of 1.30 (t, 3H), of 1.20 (d, 3H), of 0.89 (t, 6H)
5-152-CH(Me)

CH2CH2CH

Me2
0CF3H7,08-7,00 (m, 2H), of 6.68 (d, 1H), 3, 92 (m, 1H), 3,99-3,70 (user., 2H), 2,65 (m, 1H), 1,78-1,2 (m, 4H), 1.30 and 1.10 for (m, 5H), 0,86 (d, 6H)
5-162-CH(Me)

CH2CH2CH2< / br>
CH3
0CF3H7,26 (s, 1H), 7,20 (m, 1H), of 6.71 (d, 1H), 3.95 to 3,78 (user., 2H), 2,69 (m, 1H), 1,72-of 1.42 (m, 2H), 1,40-of 1.18 (m, 7H), to 0.88 (t, 3H)
5-172-CH(Me)

CH2CHMe2
0HH6,98 (s, 1H), 6,92 (d, 1H), 6,65 (d, 1H), 3,85-3,60 (user., 2H), 3,24 (DD, 2H), and 2.79 (m, 1H), 1,65 is 1.48 (m, 2H), 1,45-of 1.30 (m, 1H), 1,19 (d, 3H), of 0.90 (t, 6H)
5-182-CH(Me)

CH2CHMe2
2HH6,97 (s, 1H), 6.90 to (d, 1H), 6,65 (d, 1H), 3,82 is 3.40 (user., 2H), 3,23 (t, 2H), and 2.79 (m, 1H), 1.70 to 1,50 (m, 2H), 1.39 in (m, 1H), 1,20 (d, 3H), of 0.90 (t, 6H)
5-192-CH(Me)

CH2CHMe2
4HH6,97 (s, 1H), 6,92 (d, 1H), 6,65 (d, 1H), 4,00-3,70 (user., 2H), 3,24 (t, 2H), and 2.79 (m, 1H), 1,68 is 1.48 (m, 2H), 1,45-of 1.30 (m, 1H), 1,22 (d, 3H), of 0.89 (m, 6H)
5-202-CH(Me)

CH2CHMe2
6HH6,97 (s, 1H), 6.90 to (d, 1H), 6,65 (d, 1H), 3,24 (t, 2H), and 2.79 (m, 1H), 1,67-of 1.45 (m, 2H), 1,42-of 1.30 (m, 1H), 1,22 (d, 3H), of 0.90 (t, 6H)

Typical examples, examples of the preparation of compositions and examples of tests of the present invention described below, however, they should not be construed as limiting the scope of the invention.

When the EP 1-1

Getting 2-(1,3-dimethylbutyl)-4-[2,2,2-Cryptor-1-(trifluoromethyl)ethyl]aniline (compound No. 5-11)

Alumoweld lithium (2 g, and 52.7 mmol) suspended in tetrahydrofuran (60 ml)and then was added dropwise 2-(1,3-dimethylbutyl)-4-[1,2,2,2-titrator-1-(trifluoromethyl)ethyl]aniline (14 g, a 40.5 mmol) and the resulting mixture was stirred while boiling under reflux for 3 hours. To the reaction mixture in small portions under ice cooling was added water, and then was stirred for 10 minutes. After this was added magnesium sulfate and stirred for 10 minutes. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure to obtain 13 g of the desired compound.

Yield: 98%.

Example 1-2

Obtain N-{2-(1,3-dimethylbutyl)-4-[2,2,2-Cryptor-1-(trifluoromethyl)ethyl]phenyl}-5-chloro-1-methyl-3-cryptomaterial-4-carboxamide (compound No. 1-103)

5-Chloro-1-methyl-3-cryptomaterial-4-carboxylic acid (230 mg, 1 mmol) was dissolved in thionyl chloride (2 ml) and the solution was stirred while boiling under reflux for 2 hours. After concentration under reduced pressure the obtained acid chloride was added to a solution of 2-(1,3-dimethylbutyl)-4-[2,2,2-Cryptor-1-(trifluoromethyl)ethyl]aniline (330 mg, 1 mmol) and triethylamine (150 mg, 1.5 mmol) in tetrahydrofuran (10 ml) under ice cooling and the resulting mixture premesis is whether at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate, and then washed with water. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure and the obtained residue was separated and purified column chromatography on silica gel (hexane:ethyl acetate = 3:1) to give 233 mg of the desired compound.

Physical properties: melting point of 102-104°C. Yield: 43%.

Example 2-1

Getting 2-(1,3-dimethylbutyl)-4-[1-methoxy-2,2,2-Cryptor-1-(trifluoromethyl)ethyl]aniline (compound No. 5-13)

Sodium (533 mg, 23 mmol) was dissolved in methanol (40 ml)and then added 2-(1,3-dimethylbutyl)-4-[1,2,2,2-titrator-1-(trifluoromethyl)ethyl]aniline (2 g, 5.8 mmol) and the resulting mixture was stirred while boiling under reflux for 3 hours. The reaction mixture was concentrated under reduced pressure and the residue was diluted with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate, and then concentrated under reduced pressure and the obtained residue was separated and purified column chromatography on silica gel (hexane:ethyl acetate=6:1) to obtain 1.8 g of the desired compound.

Yield: 87%.

Example 2-2

Obtain N-{2-(1,3-dimethylbutyl)-4-[1-methoxy-2,2,2-Cryptor-1-(trifluoromethyl)ethyl]phenyl}-1,3,5-trimethylpyrazole-4-carboxamide (compound No. 1-108)

1,3,5-trimethylpyrazole-4-carboxylic acid (15 mg, 1 mmol) was dissolved in thionyl chloride (5 ml) and the solution was stirred while boiling under reflux for 2 hours. The reaction mixture was concentrated under reduced pressure and the obtained acid chloride was added to a solution of 2-(1,3-dimethylbutyl)-4-[1-methoxy-2,2,2-Cryptor-1-(trifluoromethyl)ethyl]aniline (345 mg, 1 mmol) and triethylamine (150 mg, 1.5 mmol) in tetrahydrofuran (10 ml) under ice cooling, after which the resulting mixture was boiled under reflux for 2 hours. The reaction mixture was diluted with ethyl acetate, and then washed with water. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure and the obtained residue was separated and purified column chromatography on silica gel (hexane:ethyl acetate = 1:2) to obtain 200 mg of the desired compound.

Physical properties: melting point of 94-96°C. Yield: 41%.

Example 3-1

Getting 2-(1-hydroxy-1,4-dimethylpentyl)aniline

Magnesium (960 mg, 40 mmol), and then a catalytic amount of iodine was added to diethyl ether (15 ml), then slowly boiling under reflux was added isoamylase (6,04 g, 40 mmol) and the resulting mixture was stirred while boiling under reflux for 30 minutes and then at room temperature for 30 minutes. To the obtained solution under cooling is Edom was added 2-aminoacetophenone (1.8 g, 13.3 mmol)and then stirred at room temperature for 3 hours. After this was added ammonium chloride and the resulting mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate, and then concentrated under reduced pressure to obtain 2.7 g of 2-(1-hydroxy-1,4-dimethylpentyl)aniline.

Physical properties:1H-NMR [CDCl3/TMS, values δ, (ppm)]

7,10-7,00 (m, 2H), 6,72-6,60 (m, 2H), 4,00-3,70 (user., 2H), 2,03 (m, 2H), 1.61 of (s, 3H), 1,50 (m, 2H), 1,20-1,00 (m, 1H), 0,90-of 0.83 (m, 6H).

Yield: 99%.

Example 3-2

Getting 2-(1,4-dimethylpentyl)aniline

After obtaining 2.7 g (13,1 mol) of 2-(1-hydroxy-1,4-dimethylpentyl)aniline as described in example 3-1, it was diluted with toluene and then added monohydrate p-toluensulfonate acid (225 mg) and the resulting mixture dehydrational boiling under reflux for 3 hours using traps Dean-stark. The reaction mixture was diluted with ethyl acetate, and then washed with an aqueous solution of sodium bicarbonate and saturated aqueous sodium chloride. The organic layer was dried over magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was dissolved in ethanol, and then to this solution was added 5% palladium on coal (100 mg) and the resulting mixture was stirred in hydrogen atmosphere at room temperature in the course is the development of 12 hours. The reaction mixture was filtered through celite and the residue was concentrated under reduced pressure to obtain 2.2 g of 2-(1,4-dimethylpentyl)aniline.

Physical properties:1H-NMR [CDCl3/TMS, values δ, (ppm)]

7,10 (DD, 2H), 7,02 (dt, 1H), 6,79 (dt, 1H), 6,69 (DD, 1H), 3,67 (users, 2H), 2,68 (m, 1H), 1,80-of 1.42 (m, 4H), 1.30 and 1.10 for (m, 5H), of 0.87 (d, 6H).

Yield: 87%.

Example 3-3

Getting 2-(1,4-dimethylpentyl)-4-[1,2,2,2-titrator-1-(trifluoromethyl)ethyl]aniline

2-(1,4-dimethylpentyl)aniline (1.8 g, 9.4 mmol), obtained as described in example 3-2 was dissolved in a solution (50 ml), consisting of tert-butyl methyl ether and water in the ratio of 1:1. To the resulting solution was added 1,2,2,2-titrator-1-(trifluoromethyl)ethyliodide (2,78 g, 9.4 mmol), bisulfate Tetra-n-butylamine (318 g of 0.94 mmol), sodium bicarbonate (795 mg, 9.4 mmol), and then dithionite sodium (1.63 g, 9.4 mmol) and the resulting mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted with hexane and twice washed 3h. hydrochloric acid and then aqueous sodium bicarbonate solution and saturated aqueous sodium chloride. The organic layer was dried over magnesium sulfate, and then concentrated under reduced pressure to obtain 3.28 g of the desired compound.

Physical properties:1H-NMR [CDCl3/TMS, values δ, (ppm)]

7,26 (s, 1H), 7,21 (d, 1H), 6,72 (d, 1H), 4,05-3,80 (user., 2H), or 2.67 (m, 1H), 1,78-1,40 (who, 4H), of 1.30 to 1.00 (m, 5H), of 0.85 (d, 6H).

Yield: 97%.

Example 3-4

Getting 2-(1,4-dimethylpentyl)-4-[2,2,2-Cryptor-1-(trifluoromethyl)ethyl]aniline (compound No. 5-15)

The desired compound was obtained by carrying out the reaction for 4 hours by the method described in example 1-1, except that instead of 2-(1,3-dimethylbutyl)-4-[1,2,2,2-titrator-1-(trifluoromethyl)ethyl]aniline was used 2-(1,4-dimethylpentyl)-4-[1,2,2,2-titrator-1-(trifluoromethyl)ethyl]aniline.

Yield: 82%.

Example 3-5

Obtain N-{2-(1,4-dimethylpentyl)-4-[2,2,2-Cryptor-1-(tri-permitil)ethyl]phenyl}-5-chloro-1,3-dimethylpyrazol-4-carboxamide (compound No. 1-146)

5-Chloro-1,3-dimethylpyrazol-4-carboxylic acid (349 mg, 2 mmol) was dissolved in thionyl chloride (10 ml) and the solution was stirred while boiling under reflux for 2 hours. After concentration under reduced pressure the obtained acid chloride was added to a solution of 2-(1,4-dimethylpentyl)-4-[2,2,2-Cryptor-1-(trifluoromethyl)ethyl]aniline (682 mg, 2 mmol) and triethylamine (300 mg, 3 mmol) in tetrahydrofuran (20 ml) under ice cooling and the resulting mixture was stirred while boiling under reflux for 2 hours. The reaction mixture was diluted with ethyl acetate, and then washed with water. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure and the obtained residue was separated and chiwele column chromatography on silica gel (hexane:ethyl acetate = 2:3) to obtain 200 mg of the desired compound.

Physical properties: the refractive index 1,4905 (20,4°). Yield: 41%.

Example 4-1

Getting 4-iodine-2-(1,3-dimethylbutyl)aniline

In methanol was dissolved 2,53 g (10 mmol) of iodine, and to this solution under ice cooling, was added 2-(1,3-dimethylbutyl)aniline (1.77 g, 10 mmol), then added an aqueous solution of sodium bicarbonate (1.26 g, 15 mmol) and the resulting mixture was stirred at 0°C for 4 hours. To the reaction mixture were added sodium thiosulfate and the mixture was concentrated under reduced pressure, diluted with ethyl acetate, and then washed with water. The organic layer was dried over magnesium sulfate, and the residue was separated and purified column chromatography on silica gel (hexane:ethyl acetate=10:1) to obtain a 2.71 g of the desired compound.

Yield: 89%.

Example 4-2

Getting 2-(1,3-dimethylbutyl)-4-panafcortelone

4-iodine-2-(1,3-dimethylbutyl)aniline (1.35 g, of 4.45 mmol), copper powder (0.85 grams, of 13.4 mmol) and panafcortelone (1.42 g, 5,77 mmol) was added to dimethylsulfoxide (10 ml) and the resulting mixture was stirred at 130°C for 4 hours. The mixture was filtered through celite and the filtrate was diluted with ethyl acetate and 4 times washed with water. The organic layer was dried over magnesium sulfate, and then concentrated under reduced pressure to obtain 1.24 g of the desired compound.

Physical properties:1NAMR [CDCl 3/TMS, values δ, (ppm)]

7,26 (s, 1H), 7,20 (m, 1H), 6,70 (d, 1H), 4,00-3,85 (user., 2H), 3,00 (m, 1H), 1,68 of 1.50 (m, 2H), 1,48-of 1.30 (m, 1H), 1,22 (t, 3H), were 0.94 (m, 6H).

Yield: 95%.

Example 4-3

Getting 2-(1,3-dimethylbutyl)-4-(2,2,2-triptorelin)aniline (compound No. 5-17)

Alumoweld lithium (1,62 g, 4.26 deaths mmol) was dissolved in tetrahydrofuran (20 ml)and then was added dropwise 2-(1,3-dimethylbutyl)-4-panafcortelone (974 mg, 3.3 mmol) and the resulting mixture was stirred while boiling under reflux for 3 hours. To the reaction mixture in small portions under ice cooling, was added water, and then was stirred for 10 minutes. After this was added magnesium sulfate and stirred for 10 minutes. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure, then the residue was separated and purified column chromatography on silica gel (hexane:ethyl acetate=9:1) to give 260 mg of the desired compound.

Yield: 30%.

Example 5-1

Getting 2-(1,3-dimethylbutyl)-4-nonafterburning

The desired compound was obtained by carrying out the reaction for 4 hours by the method described in example 4-2, except that instead of panafcortelone used nonoperational.

Physical properties:1H-NMR [CDCl3/TMS, values δ, (ppm)].

of 7.25 (s, 1H), 7,20 (m, 1H), of 6.71 (d, 1H), was 4.02-of 3.85 (m, 2H), and 2.79 (m, 1H), 1,68 of 1.50 (m, 2H),1,50-of 1.35 (m, 1H), 1,22 (d, 3H), of 0.90 (t, 6H).

Yield: 90%.

Example 5-2

Getting 2-(1,3-dimethylbutyl)-4-(2,2,3,3,4,4,4-hepta-forhekset)aniline (compound No. 5-18)

The desired compound was obtained by carrying out the reaction for 3 hours by the method described in example 4-3, except that instead of 2-(1,3-dimethylbutyl)-4-panafcortelone used 2-(1,3-dimethylbutyl)-4-nonafterburning.

Yield: 92%.

Example 6-1

Getting 2-(1,3-dimethylbutyl)-4-tridecafluorohexyl

The desired compound was obtained by carrying out the reaction for 4 hours by the method described in example 4-2, except that instead of panafcortelone used tridecafluorohexyl.

Physical properties:1H-NMR [CDCl3/TMS, values δ, (ppm)].

of 7.25 (s, 1H), 7,20 (m, 1H), of 6.71 (d, 1H), 4,05-a 3.87 (m, 2H), and 2.79 (m, 1H), 1,68 of 1.50 (m, 2H), 1,48-of 1.30 (m, 1H), 1,22 (d, 3H), of 0.90 (t, 6H).

Yield: 87%.

Example 6-2

Getting 2-(1,3-dimethylbutyl)-4-(2,2,3,3,4,4,5,5,6,6,6-undecafluoropentyl)aniline (compound No. 5-19)

The desired compound was obtained by stirring for 3 hours by the method described in example 4-3, except that instead of 2-(1,3-dimethylbutyl)-4-panafcortelone used 2-(1,3-dimethylbutyl)-4-tridecafluorohexyl.

Yield: 85%.

Example 7-1

Getting 2-(1,3-dimethylbutyl)-4-heptadecafluorooctane

The desired compound which was alocale by carrying out the reaction for 4 hours by the way, described in example 4-2, except that instead of panafcortelone used heptadecapeptide.

Physical properties:1H-NMR [CDCl3/TMS, values δ, (ppm)].

from 7.24 (s, 1H), 7,19 (d, 1H), 6,70 (d, 1H), 4,05-3,85 (user., 2H), 2,78 (m, 1H), 1,67 of 1.50 (m, 3H), 1,50-1,32 (m, 1H), 1,21 (d, 3H), of 0.89 (t, 6H).

Yield: 40%.

Example 7-2

Getting 2-(1,3-dimethylbutyl)-4-(2,2,3,3,4,4,5,5,6,6,6-pentadecafluoroheptyl)aniline (compound No. 5-20)

The desired compound was obtained by stirring for 3 hours by the method described in example 4-3, except that instead of 2-(1,3-dimethylbutyl)-4-panafcortelone used 2-(1,3-dimethylbutyl)-4-heptadecafluorooctane.

Yield: 58%.

Agent for pest control agricultural and fruit crops, and in particular, insecticide or acaricide for this application containing substituted aniline derivative of the present invention represented by the formula (I)or its salt, can be used as active ingredient for the control of various insects, such as insect pests of agricultural and fruit crops, insect pests of stored grain insect pests, sanitary-technical equipment, nematodes, etc. that affect the paddy rice, fruit trees, vegetable crops and other crops, flowers, ornamental plants, etc. They are about adut significant insecticidal action, for example,Lepidopteraincluding fruit-tree tortrix (Adoxophes orana fasciata), a small moth tea (Adoxophyes sp.), the moth Manchu (Grapholita inopinata), the moth Oriental peach (Grapholita molesta), svalilsya soy (Leguminovora glycinivorella), trubkovich mulberry (Olethreutes mori), trubkovich tea (Caloptilia thevivora), lilac mol (Caloptilia zachrysa), Apple leaf miner fly (Phyllonorycter ringoniella), the bark of pear (Spulerrina astraurota), small butterflies (Piers rapae crucivora), well tobacco (Heliothis sp.), the Codling moth (Laspey resia pomonella), cabbage moth (Plutella xylostella), mol cane brown (Argyresthia conjugella), peach moth (Carposina niponensis), borers of rice stem (Hilo) (Chilo suppressalis), rice moth (Cnaphalocrocis medinalis), Ognevka tobacco (Ephestia elutella), Ognevka mulberry (Glyphodes pyloalis), borers of rice yellow (Scirpophaga incertulas), Tolstoganova rice (Parnara guttata), well rice (Pseudaletia separata), grinder red (Sesamia inferens), well potrysayushey (Spodoptera litura), well beet (Spodoptera exigua), etc.;Bugsincluding, cinadco Asteraceae (Macrosteles fascifrons), Cicada rice green (Nephotettix cincticepts), Cicada brown rice (Nilaparvata lugens), Cicada rice white-winged (Sogatella furcifera), listblock citrus (Diaphorina citri), whiteflies striped (Aleurolibus taonabae), whiteflies bathtowel (Bemisia tabaci), the greenhouse whitefly (Trialeurodes vaporariorum), aphid lookupentry (Lipaphis erysimi), aphid green peach is Yu (Myzus persicae), a) wax (Ceroplastes ceriferus), San Jose scale white citrus (Pulvinaria aurantii), San Jose scale Japanese camphor (Pseudaonidia duplex), California San Jose scale (Comstockaspis perniciosa), the interior of Eastern citrus (Unapsis yanonensis), etc.;Tylenchida,including root nematode (Pratylenchus sp.), the soybean pollen beetle (Anomala rufocurpea), Japanese beetle (Popillia japonica), tobacco beetle (Lasioderma serricorne), the beetle trevorite (Lyctus brunneus), dvadtsativosmiletny Ladybird (Epilachna vigintiotopunctata), the weevil Chinese (Callosobruchus chinensis), vegetable weevil (Listroderes costirostris), corn weevil (Sitophilus zeamais), weevil cotton (Anthonomus grandis grandis), rice weevil water (Lissorhoptrus oryzophilus), of pumpkin leaf (Aulacophora femoralis), of rice leaf (Oulema oryzae), beetle-Blasco striped (Phyllotreta striolata), pine leaf (Tomicus piniperda), Colorado potato beetle (Leptinotarsa decemlineata), the Mexican bean weevil (Epilachna varivestis), Blasko dlinnoyu (Diabrotica sp.) etc.;Dipteraincluding (Dacus(Zeugodacus) cucurbitae), fly Oriental fruit (Dacus(Bactrocera) dorsalis), leaf miner fly rice (Agnomyza oryzae), the larva of the onion fly (Delia antiqua), the larva of a fly germ (Delia platura), Midge soy (Asphondylia sp.), fly home real (Musca domestica), a mosquito-Piskun (Culex pipiens pipiens), and the like;Tylenchidaincluding root nematode (Pratylenchus sp.), coffee nematode (Pratylenchus coffeae), potato cyst nematode (Globodera rostochiensis), Javanese root-knot the nematode (Meloidogyne sp.), citrus is th nematode (Tylenchulus semipenetrans), aphelenchus (Aphelenchus avenae), leaf hrizantemovogo (Aphelenchoides ritzemabosi) and the like; andTicksincluding Clasica red citrus (Panonychus citri), mite red fruit (Panonychus ulmi), spider mite (Tetranychus cinnabarinus), Kanzawa spider mite (Tetranychus Kanzawai Kishida), mite bimaculated spider mites (Tetranychus urticae Koch), Clasica red tea (Acaphylla theae), Clasica red citrus (Aculops pelekassi), Clasica tea Magenta (Calacarus carinatus), Clasica pear (Epitrimerus pyri), etc.

Agents for combating pests of agricultural and fruit crops containing substituted aniline derivative represented by the General formula (I)can be also used as a fungicide to control pests of agricultural and fruit crops, and they are highly effective fungicidal activity against various diseases. Specific examples of diseases against which the compounds of the present invention have a pronounced effect, are piricularia rice (Pyricularia oryzae), Rhizoctonia rice (Rhizoctonia solani), Helminthosporium leaf spot of rice (Cochiobolus miyabeanus), powdery mildew of various plant hosts, for example, powdery mildew of barley and wheat (Erysiphe graminis), crown rust of oats (Puccinia coronata), rust stems of other plants, late blight of tomato (Phytophtora infestans), late blight of other plants, fitit the roses or fitoterapia rot of various plants, for example, downy mildew of cucumber (Pseudoperonospora cubensis), downy mildew of grapevine (Plasmopara viticola), etc., Apple scab (Venturia inequalis), Alternaria leaf Apple (Alternaria mali), black spot of pear (Alternaria kikuchiana), melanosis of citrus (Diaporthe citri), a bacterial disease caused by bacteria of the genus Pseudomonas, such as bacteriosis cucumbers (Pseudomonas syringae pv.lachrymans) and bacterial wilt of tomato (Pseudomonas solanacearum), a bacterial disease caused by bacteria of the genus Xanthomonas, such as black rot of cabbage (Xanthomonas campestris), bacteriosis of rice (Xanthomonas oryzae) and cancer of citrus (Xanthomonas citri), and bacterial diseases, wyzwolenie by bacteria of the genusErwiniasuch as wet rot of cabbage (Erwinia carotovora), and viral diseases such as tobacco mosaic virus (tobacco mosaic tobacco mosaic), etc.

Agent for pest control agricultural and fruit crops, and in particular insecticide for use in agriculture and horticulture, which contains as active ingredient a substituted aniline derivative of the present invention of General formula (I) or its salt, has a pronounced insecticidal action on the above insect pests affecting field crops paddy rice, upland rice culture, fruit trees, vegetable crops and other crops, flowers and ornamental plants, etc. So desire the initial effect of the agent, used to combat agricultural pests and fruit crops, and in particular, the insecticide of the present invention, used in agriculture and gardening, can be achieved by making the specified agent in the water on the fields of rice-paddy, drawing on the stems and leaves of fruit trees, vegetables and other crops, flowers and ornamental plants, soil, etc. in the season expect insect pests, before or at the time of their appearance.

The agent of the present invention, designed to combat agricultural pests and fruit crops, are usually obtained in traditional forms in accordance with standard techniques of toxic chemicals.

That is substituted aniline derivative of General formula (I) or its salt, and, optionally, the adjuvant is mixed with a suitable carrier in an appropriate ratio and get a suitable preparative form such as a suspension, emulsifiable concentrate, wettable powder, granules, dusty, tablets, packets or the like, through dissolution, dispersion, suspension, mixing, impregnation, adsorption or bonding.

The inert carrier used in the present invention may be solid or liquid. Examples of the material used as a solid carrier, could the t to serve soy flour, flour from grain, wood flour, flour from tree bark, sawdust, shredded tobacco stems, crushed walnut shells, bran, powdered cellulose, vegetable residues after extraction, powdered synthetic polymers or resins, clays (e.g. kaolin, bentonite and acid clay), talc (e.g. talc and pyrophyllite), silica powder or flake quartz (e.g., diatomaceous earth, silica sand, mica and white soot [synthetic vysokodispersnye silicic acid, also called finely dispersed gidratirovannym silica or hydrated silicic acid, some of the commercially available products contain the calcium silicate as a main component]), activated carbon, powdered sulfur, pumice, calcined diatomaceous earth, ground brick, fly ash, sand, calcium carbonate, calcium phosphate and other inorganic or mineral powders, chemical fertilizers (e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and ammonium chloride) and compost. These carriers can be used both separately and in mixture.

The material used as the liquid media, which are selected from materials which are soluble or which are not soluble, but capable of dispersing active in redient with adjuvant. The following are typical examples of liquid carriers that can be used both separately and in mixture, namely: water, alcohols (e.g. methanol, ethanol, isopropanol, butanol and ethylene glycol), ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyrate and cyclohexanone), ethers (e.g. ethyl ether, dioxane, cellosolve, DIPROPYLENE ether and tetrahydrofuran), aliphatic hydrocarbons (e.g. kerosene and mineral oil), aromatic hydrocarbons (e.g. benzene, toluene, xylene, benzene and alkylnaphthalene), halogenated hydrocarbons (e.g. dichloroethane, chloroform, tetrachlorethane and chlorobenzene), ethers (e.g. ethyl acetate, diisopropylphenol, dibutyl phthalate and dioctylphthalate), amides (e.g. dimethylformamide, diethylformamide and dimethylacetamide), NITRILES (e.g. acetonitrile), and dimethyl sulfoxide.

The following are typical examples of adjuvants that are used depending on the purpose of their use, and in some cases they are used separately, and in some cases in combination with each other, if they are used.

For emulsification, dispersion, dissolution and/or wetting compounds used as the active ingredient, applied surface-active substance. As examples over OSTO-active substances can be mentioned alkalemia esters of polyoxyethylene, alkylacrylate esters of polyoxyethylene, esters of polyoxyethylene and of higher fatty acids, polyoxyethylenated, monolaurate polarizationsensitive, alkylarylsulfonate, condensation products naphtalenesulfonic acid, ligninsulfonate and esters of sulfates of higher alcohols.

In addition, to stabilize the dispersion of the compounds used as the active ingredient, its bonding and/or binding, can also be used adjuvants listed below, namely adjuvants such as casein, gelatin, starch, meticulosa, carboxymethylcellulose, Arabian gum, polyvinyl(e) alcohol(s), turpentine, oil of bran, bentonite and ligninsulfonate.

To improve the yield of solid product can also be used following adjuvants, namely adjuvants such as waxes, stearates, alkylphosphate etc.

Adjuvants, such as condensation products naphtalenesulfonic acid and polycondensate phosphates, may also be used as patinator for dispersible products.

Such adjuvants as silicone oil, may be used as antifoam.

Adjuvants, such as 1,2-benzisothiazolin-3-one, 4-chloro-3,5-Xylenol, butyl-p-hydroxybenzoate, can also be added as a preservative.

In addition, if it is necessary the mo, it can be also added functional spray agents, active amplifiers, such as a metabolic inhibitor of decomposition, such as piperonylbutoxide; substance reduce the freezing temperature, such as propylene glycol; antioxidants, such as BHT; absorbers of ultraviolet radiation, etc.

If necessary, the content of the compounds used as the active ingredient can vary, and this connection can be used in a properly selected value, comprising in the range from 0.01 to 90 wt. parts per 100 parts of the agent used to combat agricultural pests and fruit crops. For example, in doctah or granules suitable amount of the compounds used as the active ingredient is from 0.01 to 50 wt.%. In the emulsifiable concentrate or flowable wettable powders, this amount is from 0.01 to 50 wt.%.

The agent of the present invention is used to control various insect pests of agricultural and fruit crops as follows: this agrochemicals applied to the culture, which, as expected, it can be damaged by insects, or area, where the appearance or reproduction of these insect pests is undesirable, it may be applied either directly the public, or after appropriate dilution with water or suspension in water or the like, in an amount effective to combat insect pests.

The dose applied insecticide used to control pests of agricultural and fruit crops, varies depending on various factors such as the purpose of application, specific insect pests against which is applied the insecticide from the stage of plant growth, the likelihood of insect-pest, weather, environmental conditions, form of drug, and the time and place of the making of this insecticide. This quantity may, generally, be in the range from 0.001 g to 10 kg, and preferably from 0.01 g to 1 kg (compounds used as the active ingredient) 10 ar depending on the purpose of application.

The agent of the present invention, designed to combat agricultural pests and fruit crops, can be used in a mixture with other insecticides, acaricides, nematicides, fungicides, pesticides biological effect or the like to expand the circle of insect pests, against the use of these pesticides, and to increase the effective period of these pesticides or to reduce the dose. In addition, the agent of the present invention can be used in sm is si with herbicides, regulators of plant growth, fertilizers or the like, depending on conditions of use.

As examples of other vegetable insecticides, acaricides and nematicides used for the above purposes, may be mentioned are insecticides, acaricides and nematicides, usually used to combat agricultural pests and fruit crops, such as ation, trichlorfon, metamidophos, Arafat, dichlorvos, mevinphos, monocrotophos, Malathion, dimethoate, formothion, mecarbam, vamidothion, thiometon, disulfoton, oxidation, naled, methylparathion, fenitrothion, cyanophos, propafol, fenthion, prothiofos, profenofos, isofenphos, temephos, pentat, dimethylene, chlorfenvinfos, tetrachlorvinphos, Proxim, isoxathion, pyraclofos, mitigation, chlorpyrifos, chlorpropamide, predatation, diazinon, pirimiphosmethyl, fozalon, phosmet, dioxybenzone, finalpos, terbufos, ethoprophos, cadusafos, resolvents, DPS (NK-0795), fastcars, fenamiphos, solidagos, fosthiazate, isazofos, ethoprophos, fenthion, hostican, dichlofenthion, thionazin, sulprofos, fensulfothion, diamides, pyrethrin, allethrin, prallethrin, resmethrin, permethrin, tefluthrin, bifenthrin, fenpropathrin, cypermethrin, α-cypermethrin, cigalotrin, λ-cigalotrin, deltamethrin, acrinathrin, fenvalerate, esfenvalerate, flucythrinate, fluvalinate, cicloprofen, etofenprox, g is femprox, selflove, fluvalinate, methomyl, oxamyl, thiodicarb, aldicarb, alankar, cartap, metolcarb, killchar, propoxur, fenoxycarb, fenobucarb, ethiofencarb, fanatical, bifenazate, VRMS, carbaryl, primicarb, carbofuran, carbosulfan, furathiocarb, benfuracarb, aldoxycarb, diafenthiuron, diflubenzuron, teflubenzuron, hexaflumuron, novaluron, lufenuron, flufenoxuron, chlorfluazuron, the oxide fenbutatin, hydroxide tricyclohexyl, sodium oleate, potassium oleate, methoprene, hydroprene, binapacryl, amitraz, dicofol, kerzen, Chlorobenzilate, bromopropylate, tetradifon, bensultap, benoxinate, tebufenozide, methoxyfenozide, chromafenozide, propargite, acehenese, endosulfan, giovanola, chlorfenapyr, fenpyroximate, toppenberg, fipronil, tebufenpyrad, triazamate, etoxazole, hexythiazox, nicotine sulphate, nitenpyram, acetamiprid, thiacloprid, Imidacloprid, thiamethoxam, clothianidin, nidentified, fluazinam, pyriproxifen, hydramethylnon, pyrimidifen, pyridaben, cyromazine, TPIC (tripropellant), pymetrozine, clofentezine, buprofezin, thiocyclam, fenazaquin, chinomethionat, indoxacarb, polyactive complexes, milbemectin, abamectin, emamectin-benzoate, spinosad, W (Bacillus thuringiensis), azadirachtin, rotenone, hydroxypropyltrimonium starch, levamisole hydrochloride, METAM-sodium tartrate morantel, dazomet, trilam the d, Pasteuria penetrans,Monacrosporium-phymatophagumetc. as examples of the fungicides used for the above purposes, may be mentioned such fungicides used in agriculture and horticulture as sulfur, lime-sulfur mixture, basic copper sulfate, iprobenfos, edifenphos, cyclophosphates, thiram, polycarbamate, zineb, MANEB, MANCOZEB, propineb, tiopinac, thiophenemethyl, benomyl, acetate of iminoctadine, albella of iminoctadine, mepronil, flutolanil, pencycuron, parameter, leflunomid, metalaxyl, oxadixyl, cropropamide, dichlofluanid, glucolipid, CHLOROTHALONIL, kresoxim-methyl, phenoxyl (NNF-9425), hymexazol, etridiazole, perimed, procymidon, vinclozolin, iprodione, triadimefon, triflumizole, bitertanol, econazole, fluconazole, propiconazol, difenoconazol, myclobutanil, tetraconazole, hexaconazole, tebuconazole, kabekona, prochloraz, peyratout, tsyprokonazolu, isoprothiolane, fenarimol, Pyrimethanil, mepanipyrim, pirivenas, fluazinam, triforine, declomycin, AZOXYSTROBIN, thiadiazin, Captan, provenzal, acibenzolar-S-methyl (CGA-245704), phtalic, tricyclazole, pyroxylin, chinomethionat, oxolinic acid, dithianon, kasugamycin, validamycin, polyoxin, blasticidin, streptomycin and so in the Same way as examples of herbicides can be referred to herbicides such as glyphosate, sulfosate, glufosinate, b is Alatas, butamifos, asbroker, prosulfocarb, benthiocarb, perimutter, Azul, linuron, damron, benzylbromide, cycloaliphatic, chinaculture, pyrazosulfuron, azimsulfuron, imazosulfuron, trichlor, alachlor, pretilachlor, clomipram, etamesonic, mefenacet, pendimethalin, bifenox, acifluorfen, lactofen, cyhalofop-butyl, ioxynil, bromated, aloxide, sethoxydim, napropamide, indianian, pyrazolate, benzefoam, pyraflufen-ethyl, imazapic, sulfentrazone, cafestol, bentonite, oxadiazon, paraquat, Diquat, Perminova, Simazine, atrazine, deltamethrin, triazolam, Benfleet, fluthiacet-methyl, hisamoto-ethyl, bentazon, calcium peroxide, etc.

With regard to biological pesticides, the effect similar to that described above can be expected when using the agent of the present invention used to control pests of agricultural and fruit crops in the mixture, for example, viral compositions derived from nuclear polyhedrosis virus (NPV), virus granulata (GV), virus cytoplasmic polyhedrosis (CPV), entomopoxvirus (investment) and the like; microbial pesticides that are used as insecticides or nematicides, such as Monacrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidae, Pasteuria penetrans, etc.; microbial pesticides, used as fungicides, such as Trichoderma lignorum, Agrobacterium radiobctor, non-pathogenic Erwinia carotovora, Bacillus subtilis and the like; and biological pesticides that are used as herbicides, such as Xanthomonas campestris, etc.

In addition, the agent of the present invention, designed to combat agricultural pests and fruit crops, can be used in combination with biological pesticides, including natural enemies, such as wasp parasites (Encarsia formosa), wasp parasite (Aphidius colemani), Midge (Aphidoletes aphidimyza), wasp parasite (Diglyphus iseae), tick-parasite (Dacnusa sibirica), predatory mite (Phytoseiulus persimilis), predatory mite (Amblyseius cucumeris), the predatory bug (Orius sauteri) and the like; microbial pesticide, such as Beauveria brongniartii, and the like; and with pheromones, such as (Z)-10-tetradecanol-acetate, (E,Z)-4,10-tetradecanoate, (Z)-8-dodecalactam, (Z)-11-tetradecanoate, (Z)-13-ECOSAN-10-he (Z)-8-dodecenyl-acetate, (Z)-11-tetradecanoate, (Z)-13-ECOSAN-10-he, 14-methyl-1-octadecene etc.

The following are typical examples of the implementation of the present invention, but they should not be construed as limiting the scope of the invention.

Used in the examples, the terms "part" and "parts" mean part and part by mass.

An example of obtaining compositions 1

Any connection specified in tables 1-410 pieces
Xylene70 parts
N-organic10 pieces
The mixture nonylphenylether ether of polyoxyethylene and Las calcium

10 pieces

Emulsifiable concentrate was obtained by uniformly mixing the above ingredients to effect the dissolution.

An example of obtaining compositions 2

Any connection specified in tables 1-43 parts
Powdered clay82 part
Powdered diatomaceous earth15 pieces

The dust was obtained by uniform grind the above ingredients.

An example of obtaining compositions 3

Any connection specified in tables 1-45 pieces
Mixed powder of bentonite clay90 parts
Ligninsulfonate calcium5 pieces

Pellets were obtained by uniformly mixing the above ingredients and mixing the resulting mixture with a suitable amount of water, followed by granulation and drying.

An example of obtaining compositions 4

Any connection specified in tables 1-420 pieces
A mixture of kaolin and synthetic kaolin and highly dispersed silicic acid75 parts
The mixture nonylphenylether ether of polyoxyethylene and Las calcium

5 pieces

Wettable powder was obtained by uniformly mixing and dispersing the above-mentioned ingredients,

The test example 1: Insecticidal effect on the cabbage moth (Plutella xylostella)

Adult Diamondback moths were released on seedlings of Chinese cabbage to lay eggs. Two days after laying moths, seedlings, which were deferred eggs were immersed for 30 seconds in a liquid chemical composition, obtained by dilution of the drug containing as an active ingredient of each of the compounds listed in tables 1-4, up to a concentration of 500 h/million After air drying, the seedlings were left in thermostat, which was maintained at room temperature at 25°C. six days after immersion counted the number of insects hatched from eggs. Then calculate the percentage of the death of the insect by the equation below and the insecticidal effect was evaluated according to the criterion described below. The tests were carried out using three duplicates of what has been created groups of 10 insects each.

Criteria:

And --- Mortality 100%

In --- Mortality 99-90%

With --- Mortality 89-80%

D --- Mortality 79-50%.

In the assessment or above received the following connections: No. 1-2, 1-4, 1-10, 1-14, 1-17, 1-20, 1-21, 1-26, 1-28, 1-33, 1-35, 1-41, 1-48, 1-52, 1-56, 1-57, 1-58, 1-65, 1-70, 1-73, 1-82, 1-103, 1-107, 1-108, 1-132, 1-133, 1-143, 1-145, 1-146, 1-163, 1-164, 3-2, 3-3, 3-4, 3-10, 3-12, 4-1, 4-4, and 4-5.

The test example 2: Insecticidal effect on the tea tortrix (Adoxophyes sp.)

The tea leaves were immersed for 30 seconds in a liquid chemical composition, obtained by dilution of the drug containing as an active ingredient of each of the compounds listed in tables 1-4, up to a concentration of 500 h/million After air drying the tea leaves were placed in a plastic Petri dish with a diameter of 9 cm and was inoculable leafroller larvae tea, after which the Cup was left in thermostat, which was maintained at room temperature at 25°C and humidity of 70%. Eight days after inoculation were counting the number of dead and living individuals. Then calculate the percentage of the death of the insect by the equation given below, and insecticidal activity was evaluated by the following criteria specified in test example 1. The tests were carried out using three duplicate groups of 10 insects each.

In the assessment of the ku At or above received the following connections: nos: 1-52, 1-60, 1-103, 3-12, 3-28, 3-30 and 3-31.

The test example 3: Acaricide effect on mite bimaculated spider mites (Tetranychus urticae)

From the leaves of kidney beans cut leaf disks of 2 cm in diameter, these discs were placed on wet filter paper was inoculable adult females bimaculated spider mite, and then on these disks evenly on the rotating table was sprayed with 50 ml of the liquid chemical composition, obtained by dilution of the drug containing as an active ingredient of each of the compounds listed in tables 1-4, up to a concentration of 500 h/million After spraying the leaf disks were left in thermostat, which was maintained at room temperature at 25°C. two days after spraying were counting the number of dead insects and evaluated acaricide action by the criterion described in test 1. The tests were carried out using two duplicate groups of 10 insects each.

As a result of the above tests, it was found that the activity that scored At or above had the following compounds: 1-22, 1-23, 1-25, 1-26, 1-34, 1-39, 1-40, 1-51, 1-52, 1-54, from 1-60 to 1-62, 1-65, 1-70 to 1-73, 1-78, 1-81, 1-82, 1-103, 1-104, 1-106 to 1-109, 1-119, 1-132, 1-143, 1-146, 3-13, 3-21, 3-30 to 3-32 and 4-3.

The test example 4: Insecticidal activity of the green peach aphid (Myzus persicae)

Each of the C plants of Chinese cabbage were planted in plastic pots with a diameter of 8 cm and a height of 8 cm and these plants were propagated green peach aphid. Then the stems and leaves were sprayed with a sufficient amount of liquid chemical composition, obtained by dilution of the drug containing as an active ingredient of each of the compounds listed in tables 1-4, up to a concentration of 500 h/million After air drying, the pots were left in the greenhouse. Six days after spraying were counting the number of insects green peach aphid parasites on each plant Chinese cabbage, and figured acaricide effect, which was evaluated according to the criterion described below.

The destruction efficiency (%) = 100- [(T x Sa)/TA x C)] x 100

TA: the number of parasites before spraying in the treated group,

T: the number of parasites after spraying in the treated group,

Sa: the number of parasites before spraying in untreated group,

With: the number of parasites after spraying in untreated group,

Assessment criteria:

A: the efficiency of destruction of 100%

In: efficiency of destruction 99-90%

From: the efficiency of destruction 89-80%

D: the effectiveness of destruction 79-50%.

As a result of the above tests, it was found that the activity that scored At or above had the following connections: 1-4, 1-8, 1-25, 1-35, 1-41, 1-52, 1-65, 1-81, 1-87, 1-106 - 1-108, 1-146, 3-27, 3-13, 3-34 and 4-1.

The test example 5: Inhibitory effect against powdery mildew of barley

In sagindie in pots of barley plants at stage 1 of the sheet was inoculable spores of the fungus powdery mildew (Erysiphe graminis hordei) by means of spraying. After one day, the plants were sprayed liquid chemical composition, obtained by dilution of the drug containing as an active ingredient of each of the compounds listed in table 1, table 3 and table 4, concentrations up to 200 h/million Then these vessels were left in thermostat, which was maintained at room temperature at 25°C. one week after inoculation was measured lesions of each sheet and the obtained value was compared with the area of the untreated plots, while the inhibitory effect was evaluated according to the criterion described below.

Assessment criteria:

A: the effectiveness of suppression 100-95%

In: the effectiveness of suppression 94-80%

From: the effectiveness of suppression 79-60%

D: the effectiveness of suppression 59-0%.

As a result of the above tests, it was found that the activity that scored At or above had the following compounds: 1-5, 1-12, 1-23, 1-30, 1-45, 1-47, 1-52, 1-54, 1-83, 1-133, 3-30, 3-31 and 4-3.

1. Substituted aniline derivative represented by the General formula (I)

where R1represents a hydrogen atom, (C1-C6)alkyl group;

R2represents a hydrogen atom, a halogen atom or halogen(C1-C6)alkyl group;

R3represents a hydrogen atom; a halogen atom; and (C1-C )alkyl group; a hydroxyl group or(C1-C6)alkoxygroup;

t is 1, m is an integer 0,

each X, which may be the same or different, represents (C2-C8)alkyl group, hydroxy (C1-C6)alkyl group or (C3-C6)cycloalkyl (C1-C6)alkyl group;

n is an integer from 1 to 2;

in addition, two adjacent X on the aromatic ring, taken together, may form a condensed ring,

Z represents an oxygen atom

Q means the Deputy represented by any of formula Q1-Q3, Q6, Q8-Q12, Q14-Q19, Q21 and Q23:

where each of the Y1that may be the same or different, represents a halogen atom; and (C1-C6)alkyl group; a halogen(C1-C6) alkyl group; a (C2-C6)alkenylacyl; and (C1-C6)alkoxygroup; and (C1-C6)alkylthiols; and (C1-C6)alkylsulfonyl group; and (C1-C6) alkylsulfonyl group; a substituted phenyl group having one Deputy, selected from halogen atoms, or fenoxaprop;

Y2is (C1-C6 )alkyl group or a halogen(C1-C6) alkyl group;

Y3represents a hydrogen atom, (C1-C6)alkyl group, halogen (C1-C6)alkyl group or a substituted phenyl group having one or more substituents, which may be the same or different and are selected from halogen atoms or halogen (C1-C6) alkyl groups;

p represents an integer from 1 to 2, q represents an integer from 0 to 2 and r represents an integer from 0 to 2.

2. The chemical for pest control agricultural and fruit crops, characterized in that it includes substituted aniline derivative according to claim 1 as an active ingredient and is an insecticide, fungicide or acaricide designed for use in agriculture and horticulture.

3. Method of making chemical for pest control agricultural and fruit crops, characterized by the application of chemicals to control pests of agricultural and fruit crops according to claim 2 on a protected plant or in the soil at a dose effective for protecting useful plants against pests.

4. Substituted aniline derivative represented by the General formula (II):

where R1represents a hydrogen atom, (the 1-C6)alkyl group;

R2represents a hydrogen atom, a halogen atom or halogen(C1-C6) alkyl group;

R3represents a hydrogen atom, halogen atom, (C1-C6)alkyl group, a hydroxyl group, or(C1-C6)alkoxygroup;

t is 1, a m is 0,

each X, which may be the same or different, represents (C2-C8)alkyl group; a hydroxy(C1-C6)alkyl group or (C3-C6)cycloalkyl (C1-C6)alkyl group;

n is an integer from 1 to 2,

in addition, two adjacent X on the aromatic ring, taken together, may form a condensed ring.



 

Same patents:

The invention relates to new derivatives of amidine General formula (I’)

where it is:

in which R1, R2and R3HE or1-C6alkyl, C1-C6alkoxy, R4- H1-C6alkyl, R5- H1-C6alkyl or the radical:

where R10, R11and R12- OH or H, R13- H1-C6alkyl; or the radical:

where R18, R19and R20- H, HE, C1-C6alkyl, R21and R22- H, C1-C6alkyl, or R21-alkylsulfonyl, alkylsulfonyl, alkylaryl, and R22- H or the radical:

where T is -(CH2)k-, k = 1, 2, R27- H, C1-C6alkyl

The invention relates to compounds of formula (I)

in which f represents phenylenebis radical, a represents the radical

in which Rl, R2, R3, R4, R5represent independently a hydrogen atom, IT is a group or an unbranched or branched alkyl or alkoxyalkyl having from 1 to 6 carbon atoms; R11represents a hydrogen atom, an unbranched or branched alkyl radical having from 1 to 6 carbon atoms, or the radical

in which Rl, R2, R3, R4, R5represent independently a hydrogen atom, IT is a group or an unbranched or branched alkyl or alkoxyalkyl having from 1 to 6 carbon atoms; b is a thiophene; W is absent or represents an Association or S; X represents a bond or a radical -(CH2)k-NR16-, -O-, -CO-, -NR16-CO-, and so forth, and k is 0 or 1; Y represents a bond or a radical selected from the radicals -(CH2)m-, -(CH2)m-O-(CH2)n, -(CH-Q-(CH2)n; and Q represents pieperazinove radical, m and n are equal to integers from 0 to 6; R16, R17, R18represent independently a hydrogen atom, or a salt of the compounds

The invention relates to amide derivative of the formula I

< / BR>
where R3represents (1-6C)alkyl or halogen; m is 0, 1, 2 or 3; R1represents hydroxy, halogen, trifluoromethyl, nitro, amino, (1-6C)alkyl, (2-6C)alkenyl, (2-6C)quinil, (1-6C)alkoxy, (1-6C)alkylamino, di-[(1-6C)alkyl] amino, amino-(2-6C)alkylamino, (1-6C)alkylamino-(2-6C)alkylamino etc

The invention relates to inhibitors of potassium channel, in particular a derivative of tetrahydronaphthalene formula (I) or their pharmaceutically acceptable salts, stereoisomers, crystalline or amorphous forms

< / BR>
where t is 1; a and b each represent H; R1represents aryl, optionally substituted by one or more groups selected from lower alkyl, lower alkoxy, nitro, trifloromethyl, triptoreline; aromatic 5-membered monocyclic system which consists of carbon atoms and contains sulfur as one heteroatom; a saturated 5-membered monocyclic system which consists of carbon atoms and contains nitrogen as one heteroatom, which is optionally substituted by aralkyl, and aryl optionally substituted with halogen; provided that when R1represents optionally substituted aryl, R1is not dialkoxybenzene; Y2represents (CH2)qwhere q is 0; X2is SO2; R3represents H, lower alkyl, in which one hydrogen atom substituted aromatic 6-membered monocyclic system which consists of atom N; R2represents aryl, optionally substituted by one or more groups selected from lower alkyl, lower alkoxy, nitro, trifloromethyl, triptoreline; aromatic 5-membered monocyclic system which consists of carbon atoms and contains sulfur as one heteroatom; a saturated 5-membered monocyclic system which consists of carbon atoms and contains nitrogen as one heteroatom, which is optionally substituted by aralkyl, and aryl optionally substituted with halogen; Y1represents (CH2)pwhere p is 1; NS=SN or ethinyl; X1is C=O or (CH2)nwhere n is 0, 1 or 2; R4represents H, lower alkyl, in which one hydrogen atom substituted aromatic 6-membered monocyclic system which consists of carbon atoms and contains nitrogen as heteroatom

The invention relates to the field of medicine and relates to a method of increasing the expression of molecular chaperone cell and/or increasing the activity of molecular chaperones in cells by treating the cells an effective amount of hydroxylamine derivative of the formula (I) or (II), as well as to new derivatives of hydroxylamine and farmkompanijam based on them

The invention relates to new compounds for combating pests, in particular derivatives carbanilide and fungicide-insecticidal tool based on them

The invention relates to Amida aminodiphenylamine acid I in which R1, R2each independently of one another denotes N, And, moreover, one of the residues R1or R2in all cases has a value other than H; R1and R2together represent alkylene with 3-5 C-atoms, R3and R4each independently of one another denotes N or C1-C4-alkoxy; R3and R4together denote also-O-CH2-O - or-O-CH2-CH2-O-; And denotes alkyl with 1-6 C-atoms, R5means-X-Y, X represents CO, Y represents a phenyl or cyclohexyl, unsubstituted monosubstituted COOH or cooa, n denotes 1, 2 or 3, as well as their physiologically acceptable salts

The invention relates to amide derivative of the formula I

< / BR>
where R3represents (1-6C)alkyl or halogen; m is 0, 1, 2 or 3; R1represents hydroxy, halogen, trifluoromethyl, nitro, amino, (1-6C)alkyl, (2-6C)alkenyl, (2-6C)quinil, (1-6C)alkoxy, (1-6C)alkylamino, di-[(1-6C)alkyl] amino, amino-(2-6C)alkylamino, (1-6C)alkylamino-(2-6C)alkylamino etc

The invention relates to new chemical compounds, namely, esters of 2-furfurylamine-2-tsianuksusnogo acid of General formula

< / BR>
where R: CH2CF3(Ia), CH(CF3)2(IB), CH2(CF2)2CF3(IB), CH2(CF2)4H (Iك), CH2PhX (Ia), CH2C(CH3)(X)2(S), CH2C2H5)(X)2(AI), CH2WITH(X)3(IK),

when X

< / BR>
These compounds can be used as an inhibitor to prevent premature polymerization of unsaturated compounds in their synthesis, processing and storage, such as methyl methacrylate, styrene, dimethylphenylcarbinol, ethyl-2-cyanoacrylate and other

The invention relates to dimethylpolysiloxene General formula

< / BR>
in which the radicals R1and R2may be the same or different, represents hydrogen, C2-C6- alkyl, C3-C6-cycloalkyl, C3-C6alkenyl,

C2-C6-quinil, C1-C3-halogenated, benzoyloxy group containing substituents, benzoylamino, which can also contain one or two Deputy, C2-C6-alkanolamines, C3-C6-cycloalkylcarbonyl, benzyl group which may contain substituents, the phenyl group with possible alternates, and other substituents, provided that at the same time R1and R2are not hydrogen atoms, the second condition is that one of R1and R2is not unsubstituted phenyl group when the other one represents a hydrogen atom, and the third condition is one of R1and R2in anthopology is not an aniline ring, C2-C6-alkyl, C3-C6-cycloalkyl or C2-C6-alkoxygroup when the other one represents a hydrogen atom

The invention relates to new methods of obtaining salt orthocarbonate acids or alcoholate hem-triolo having the structural formula R-Me where R is phenyl, furyl, R1-CH= CH-, CH3-(CH= CH)2- CH= C-CH3; Me - Na, K; Rlis phenyl, furyl, used as an intermediate reagents in organic synthesis, as well as in the printing industry for the regeneration of aluminum plates

The invention relates to new derivatives of benzothiadiazole, benzoxazoles and benzodiazines formula I in free base form or in the form of a pharmaceutically acceptable acid salt additive that can be used as an anxiolytic drug in the treatment of any condition, which is associated with increased endogenous levels of CRF or in which violated the regulation of the hPa system (hypothalamic - pituitary), or various diseases that are caused by CRF1or the manifestation of which contributes CRF1such as arthritis, asthma, allergies, anxiety, depression, etc

The invention relates to new heterocyclic substituted phenoxyacetamide, methods for their preparation and use as a means protivodiareynogo
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