Substituted anilide derivative of pyrazole-carbonic acid or its salt, its intermediate compound, agent for application in agriculture and gardening and its application

FIELD: agriculture.

SUBSTANCE: substituted pyrazole-carbonic anilide derivatives of formula (I) are described, where R1 represents H, alkyl, alkyl carbonyl, alkenyl carbonyl, phenyl alkyl, phenyl carbonyl; R2 represents H, halogen, alkoxy; G represents alkyl, alkenyl; Z represents O; X represents H, halogen, alkyl; Y1 represents alkyl, alkenyl; Y2 represents halogen, C1-C6alkyl, m is equal to 1 or 2; and n is equal to 1, and their salts, acaricide for agriculture, such as pyrazole carbonic anilide derivatives of formula (I) and method for its application. Intermediate compound of formula (II) is also described, as well as 1.3-dimethyl-5-trifluoromethylpyrazole-4-carbonic acid.

EFFECT: improved use of new acaricides.

12 cl, 5 tbl, 20 ex

 

The present invention relates to substituted pyrazolecarboxylate derivatives or their salts, to their intermediate compounds and agents for agriculture, in particular to insecticides or acaricides containing these compounds as active ingredient, and the method of their application.

Usually substituted pyrazolecarboxylate derivatives, similar to the present invention, as is known, are useful as insecticides, fungicides or acaricides for agriculture (for example, patent application of Japan JP-A-2003-48878, JP-A-2004-189738 and JP-A-2004-269515). In the patent application of Japan JP-A-2003-48878 described substituted pyrazolecarboxylate derivatives. However, the substituents in the aniline residue for the most part limited to the substituents in position 2, the substituent in position 3 represents only the methyl group and the compound described in the present invention, where an alkyl group having 2 or more carbon atoms is introduced at position 3, is not included in the list of these compounds. Moreover, the form with the methyl group in position 3, specifically described in it do not shows acaricidal activity. In the patent application of Japan JP-A-2004-189738 described substituted pyrazolecarboxylate derivatives. However, the substituents in the aniline residue limited alkoxygroup, alkylthiol and Alki the amino group, and the connection described in the present invention, where an alkyl group having 2 or more carbon atoms, directly entered in position 3, is not even included in the list of connections. In the patent application of Japan JP-A-2004-269515 described substituted pyrazolecarboxylate derivatives. However, only describes the amide compound with heterocyclisation, and substituted pyrazolecarboxylate derivatives of the present invention are not described.

When growing agricultural and garden plants damage by harmful insects, remains a serious problem, and the development of new agents for agriculture, in particular the development of insecticides and acaricides is desirable due to the generation of harmful insects that are resistant to known agents and the like. Because they are demanded by various agricultural practices, labor-saving, due to the increase in the number of older workers in agriculture, you must also create agents for agriculture with properties suitable for such agricultural work with labor saving, in particular insecticides and acaricides.

The authors of the present invention have continued extensive studies on the development of new agents for agriculture, in particular insecticides and acaricides and found what in the wide range of compounds described in the above prior art substituted pyrazolecarboxylate derivative represented by the formula (I), where pyrazol ring is selected as the remainder of the heterocyclic carboxylic acid, and a specific Deputy entered in the aniline residue in position 3, demonstrate excellent controlling effect as acaricides, as a rule, are not predictable on the contents described in the above references to the previous level. In addition, the authors found that the intermediate compounds of the compounds, i.e. the substituted aniline derivative represented by the formula (II), and 1,3-dimethyl-5-cryptomaterial-4-carboxylic acid or its salt are novel compounds unknown in the links on the previous level, and are useful as intermediates for various derivatives having physiological activity, such as pharmaceuticals, pesticides and the like, and thus have completed the present invention.

Accordingly, the present invention relates to substituted pyrazolecarboxylate derivative represented by the formula (I):

(I)

where R11a is a) a hydrogen atom, 2a) C1-C8alkalinuria, 3a) Halogens1-C6alkyl group, 4a) C1-C6alkylcarboxylic group 5a)

Halogens1-C6alkylcarboxylic group 6a) C2-C6alkenylboronic group 7a) Halogens2-C6alkenylboronic group 8a) C1-C6alkylcarboxylic1-C6alkyl group, 9a) C3-C6cycloalkyl group, 10a) Halogens3-C6cycloalkyl group, 11a) C3-C6cycloalkyl1-C6alkyl group, 12a) Halogens3-C6cycloalkyl1-C6alkyl group, 13a) C2-C6alkenylphenol group, 14a) Halogens2-C6alkenylphenol group, 15a) C2-C6alkylamino group, 16a) Halogens2-C6alkylamino group, 17a) C1-C10alkoxyl1-C6alkyl group, 18a) Halogens1-C6alkoxyl1-C6alkyl group, 19a) C2-C6alkenylacyl1-C6alkyl group, 20a) C1-C6alkoxyl1-C6alkoxyl1-C6alkyl group, 21a) C1-C6alkylthio1-C6alkyl group, 22a) Halogens1-C6alkylthio1-C6alkyl group, 23a) C1-C6alkylsulfonyl1-C6alkyl group, 24a) Halogens1-C6alkylsulfonyl1-C6alkyl group, 25a) C 1-C6alkylsulfonyl1-C6alkyl group 26a) Halogens1-C6alkylsulfonyl1-C6alkyl group, 27a)

menos1-C6alkylamino1-C6alkyl group, 28a) dis1-C6alkylamino1-C6alkyl group, where the alkyl groups are the same or different, 29a) panels1-C6alkoxyl1-C6alkyl group, 30a) substituted phenyls1-C6alkoxyl1-C6alkyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 31a) C1-C16alkoxycarbonyl group, 32a) 1-C6alkoxyl1-C6alkoxycarbonyl group, 33a) Halogens1-C6alkoxycarbonyl group, 34a) C2-C6altneratively group, 35a) C1-C6alkylthiomethyl group, 36a) mono1-C6alkylaminocarbonyl group 37a) dis1-C6alkylaminocarbonyl group, where the alkyl groups are the same or different, 38a) C1-C6alkoxycarbonyl1-C6alkyl group, 39a) C1-C6alkylsulfonyl group, 40a) Halogens1-C6alkylsulfonyl group, 41a) tsianos1-C6alkyl group, 42a) panels1-C6alkyl group, 43a) substituted phenyls1-C6alkyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6 alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 44a) phenylcarbonylamino group, 45a) substituted phenylcarbonylamino group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o)

dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 46a) geterotsiklicheskikh group, 47a) substituted geterotsiklicheskikh group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl groups, f C 1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o)

dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 48a) phenoxycarbonyl group, 49a) substituted phenoxycarbonyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same is akovali or different, and (p) C1-C6alkoxycarbonyl group, 50a) venoxis1-C6alkylcarboxylic group, 51a) substituted venoxis1-C6alkylcarboxylic group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group 52a) phenylsulfonyl group, 53a) substituted phenylsulfonyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C 6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group 54a) dis1-C6alkylphosphonium, where the alkyl groups are the same or different, 55a) dis1-C6alkylphosphonium, where the alkyl groups are the same or different, 56a) N-C1-C6alkyl-N-C1-C6alkoxycarbonylmethyl, 57a) N-C1-C6alkyl-N-C1-C6alkoxycarbonyl1-C6alkylammonium, 58a) dis1-C6alkylammonium, where the alkyl groups are the same or different, 59a) C3-C6cycloalkylcarbonyl group, 60a) Halogens3-C6cycloalkylcarbonyl group, 61a) C1-C6alkyls3-C6cycloalkylcarbonyl group, 62a) Halogens1-C6alkyls3-C6cycloalkylcarbonyl group, 63a) panels1-C6alkylcarboxylic group, 64a) substituted phenyls1-C6alkali manilow group, having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o)

dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 65a) panels3-C6cycloalkylcarbonyl group, 66a) substituted phenyls3-C6cycloalkylcarbonyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl GRU is dust, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 67a) C3-C6cycloalkyl1-C6alkylcarboxylic group, 68a) C1-C6alkoxyl1-C6alkylcarboxylic group, 69a) Halogens3-C6cycloalkyl1-C6alkylcarboxylic group, 70a) venoxis1-C6alkoxycarbonyl group, 71a) substituted venoxis1-C6alkoxycarbonyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino PPI, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 72a) C1-C6alkylcarboxylic1-C6alkyl group, 73a) C1-C6alkylcarboxylic1-C6alkylcarboxylic group or 74a) C1-C6alkoxycarbonyl1-C6alkylcarboxylic group;

R21b is a) a hydrogen atom, 2b) halogen atom, 3b) C1-C6alkyl group, 4b) Halogens1-C6alkyl group, 5b) cyano, 6b) a hydroxy-group, 7b) C1-C6alkoxygroup, 8b) Halogens1-C6alkoxygroup, 9b) C1-C6alkoxyl1-C3alkoxygroup, 10b) Halogens1-C6alkoxyl1-C3alkoxygroup, 11b) C1-C6alkylthio1-C3alkoxygroup, 12b) Halogens1-C6alkylthio1-C3alkoxygroup, 13b) C1-C6alkylsulfonyl1-C3alkoxygroup, 14b)

Halogens1-C6alkylsulfonyl1-C3alkoxygroup, 15b) C1-C6alkylsulfonyl1-C3alkoxygroup, 16b) Halogens1-C6alkylsulfonyl1-C3alkoxygroup, 17b) mono1-C6alkylamino1-C3alkoxygroup, 18b) dis1-C6alkylamino1-C3 alkoxygroup, where the alkyl groups are the same or different, 19b) C1-C6allylthiourea, 20b) Halogens1-C6allylthiourea, 21b) C1-C6alkylsulfonyl group, 22b) Halogens1-C6alkylsulfonyl group, 23b) C1-C6alkylsulfonyl group, 24b) Halogens1-C6alkylsulfonyl group, 25b) amino group, 26b) mono1-C6alkylamino, 27b) dis1-C6alkylamino, where the alkyl groups are the same or different, 28b) fenoxaprop, 29b) is substituted by fenoxaprop having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxy is arbonelli group, 30b) phenylthiourea, 31b) is substituted by phenylthiourea having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 32b) phenylsulfinyl group, 33b) substituted phenylsulfinyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Gal who gens 1-C6alkylsulfonyl group, j) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 34b) phenylsulfonyl group, 35b) substituted phenylsulfonyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 36b) panels1-C6alkoxygroup or 37b) substituted phenyls1-C6alkoxygroup having on the ring one or more objects is s or different substituents, selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group;

G represents 1c) C2-C10alkyl group, 2c) Halogens2-C10alkyl group, 3c) C3-C10alkenylphenol group, 4c) Halogens3-C10alkenylphenol group, 5c) C3-C10alkylamino group, 6c) Halogens3-C10alkylamino group, 7c) C3-C10cycloalkyl group, 8c) substituted C3-C10cycloalkyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) C1-C6alkyl groups and c) Halogens1-C6alkyl group, 9c) C3-C10cycloalkenyl group, 10c) for sennou C 3-C10cycloalkenyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) C1-C6alkyl groups and c) Halogens1-C6alkyl group, 11c) C3-C8cycloalkyl1-C6alkyl group or 12c) Halogens3-C8cycloalkyl1-C6alkyl group;

Z represents an oxygen atom or a sulfur atom;

X may be the same or different and represent 1d) a hydrogen atom, 2d) halogen atom, 3d) cyano, 4d) of the nitrogroup, 5d) C1-C6alkyl group or 6d) Halogens1-C6alkyl group;

Y1represents 1e) a hydrogen atom, 2e) C1-C6alkyl group, 3e) Halogens1-C6alkyl group, 4e) C2-C6alkenylphenol group, 5e) Halogens2-C6alkenylphenol group, 6e) C2-C6alkylamino group, 7e) Halogens2-C6alkylamino group, 8e) C1-C6alkoxyl1-C6alkoxyl1-C6alkyl group, 9e) hydraxis1-C6alkyl group, 10e) C1-C6alkylcarboxylic1-C6alkyl group, 11e) C3-C6cycloalkyl group, 12e) Halogens3-C6cycloalkyl group, 13e) C3-C6cycloalkyl1-C6alkyl gr the PPU, 14e) Halogens3-C6cycloalkyl1-C6alkyl group, 15e) C1-C6alkylsulfonyl group, 16e) Halogens1-C6alkylsulfonyl group, 17e) C1-C6alkylthio1-C6alkyl group, 18e) Halogens1-C6alkylthio1-C6alkyl group, 19e) C1-C6alkylsulfonyl1-C6alkyl group, 20e) Halogens1-C6alkylsulfonyl1-C6alkyl group, 21e) C1-C6alkylsulfonyl1-C6alkyl group, 22e) Halogens1-C6alkylsulfonyl1-C6alkyl group, 23e) mono1-C6alkylamino1-C6alkyl group, 24e) dis1-C6alkylamino1-C6alkyl group, where the alkyl groups are the same or different, 25e) phenyl group, 26e) substituted phenyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6al is ylsulphonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group;

Y2may be the same or different and represent 1f) a hydrogen atom, 2f) halogen atom, 3f) cyano, 4f) the nitrogroup, 5f) hydroxyl group, 6f) mercaptopropyl, 7f) amino group, 8f) carboxyl group, 9f) C1-C6alkyl group, 10f) Halogens1-C6alkyl group, 11f) C2-C6alkenylphenol group, 12f) Halogens2-C6alkenylphenol group, 13f) C2-C6alkylamino group, 14f) Halogens2-C6alkylamino group, 15f) Tris1-C6alkylsilanes2-C6alkylamino group, where the alkyl groups are the same or different, 16f) panels2-C6alkylamino group, 17f) C1-C6alkoxyl1-C6alkoxyl1-C6alkyl group, 18f) hydraxis1-C6alkyl group, 19f) C1-C6alkylcarboxylic1-C6alkyl group, 20f) C3-C6cycloalkyl group, 21f) Halogens3-C6cycloalkyl group, 22f) C3-C6cycloalkyl1-C6alkyl gr the PPU, 23f) Halogens3-C6cycloalkyl1-C6alkyl group, 24f) C1-C6alkoxygroup, 25f) Halogens1-C6alkoxygroup, 26f) C1-C6alkoxyl1-C6alkoxygroup, 27f) Halogens1-C6alkoxyl1-C6alkoxygroup, 28f) panels1-C6alkoxygroup, 29f) C1-C6alkoxyl1-C6alkyl group, 30f) Halogens1-C6alkoxyl1-C6alkyl group, 31f) C1-C6allylthiourea, 32f) Halogens1-C6allylthiourea, 33f) C1-C6alkylsulfonyl group, 34f) Halogens1-C6alkylsulfonyl group, 35f) C1-C6alkylsulfonyl group, 36f) Halogens1-C6alkylsulfonyl group, 37f)1-C6alkylthio1-C6alkyl group, 38f) Halogens1-C6alkylthio1-C6alkyl group, 39f) C1-C6alkylsulfonyl1-C6alkyl group, 40f) Halogens1-C6alkylsulfonyl1-C6alkyl group, 41f) C1-C6alkylsulfonyl1-C6alkyl group, 42f) Halogens1-C6alkylsulfonyl1-C6alkyl group, 43f) mono1-C6alkylamino, 44f) dis1-C6alkylamino, where the alkyl groups are the same or once the ranks, 45f) phenylaminopropyl, range from 46f) mono1-C6alkylamino1-C6alkyl group, 47f) dis1-C6alkylamino1-C6alkyl group, where the alkyl groups are the same or different, 48f) phenyl group, 49f) substituted phenyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 50f) fenoxaprop, 51f) replaced fenoxaprop having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1 -C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 52f) heterocyclic group or 53f) substituted heterocyclic group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same and which are different, and (p) C1-C6alkoxycarbonyl group;

m is 1 or 2; and

n is an integer from 1 to 3,

their salts and agents for agriculture, containing the compound as an active ingredient, and to methods of their use.

In addition, the present invention also relates to substituted aniline derivative represented by the formula (II), which are intermediate compounds:

where R11a is a) a hydrogen atom, 2a) C1-C8alkyl group, 3a) Halogens1-C6alkyl group, 4a) C1-C6alkylcarboxylic group 5a) Halogens1-C6alkylcarboxylic group 6a) C2-C6alkenylboronic group 7a) Halogens2-C6alkenylboronic group 8a) C1-C6alkylcarboxylic1-C6alkyl group, 9a) C3-C6cycloalkyl group, 10a) Halogens3-C6cycloalkyl group, 11a) C3-C6cycloalkyl1-C6alkyl group, 12a) Halogens3-C6cycloalkyl1-C6alkyl group, 13a) C2-C6alkenylphenol group, 14a) Halogens2-C6alkenylphenol group, 15a) C2-C6alkylamino group, 16a) Halogens2-C6alkylamino group, 17a) C1-C10alkoxyl1-C6alkalinuria, 18a) Halogens1-C6alkoxyl1-C6alkyl group, 19a) C2-C6alkenylacyl1-C6alkyl group, 20a) C1-C6alkoxyl1-C6alkoxyl1-C6alkyl group, 21a) C1-C6alkylthio1-C6alkyl group, 22a) Halogens1-C6alkylthio1-C6alkyl group, 23a) C1-C6alkylsulfonyl1-C6alkyl group, 24a) Halogens1-C6alkylsulfonyl1-C6alkyl group, 25a) C1-C6alkylsulfonyl1-C6alkyl group, 26a) Halogens1-C6alkylsulfonyl1-C6alkyl group, 27a) mono1-C6alkylamino C1-C6alkyl group, 28a) dis1-C6alkylamino1-C6alkyl group, where the alkyl groups are the same or different, 29a) panels1-C6alkoxyl1-C6alkyl group, 30a) substituted phenyls1-C6alkoxyl1-C6alkyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1 6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 31a) C1-C16alkoxycarbonyl group, 32a) C1-C6alkoxyl1-C6alkoxycarbonyl group, 33a) Halogens1-C6alkoxycarbonyl group, 34a) C2-C6altneratively group, 35a) C1-C6alkylthiomethyl group, 36a) mono1-C6alkylaminocarbonyl group 37a) dis1-C6alkylaminocarbonyl group, where the alkyl groups are the same or different, 38a) C1-C6alkoxycarbonyl1-C6alkyl group, 39a) C1-C6alkylsulfonyl group, 40a) Halogens1-C6alkylsulfonyl group, 41a) tsianos1-C6alkyl group, 42a) panels1-C6alkyl group, 43a) substituted phenyls1-C6alkyl group having on the ring one or more identical or different substituents, wybran the x from a) a halogen atom, b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 44a) phenylcarbonylamino group, 45a) substituted phenylcarbonylamino group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono 1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 46a) geterotsiklicheskikh group, 47a) substituted geterotsiklicheskikh group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 48a) phenoxycarbonyl group, 49a) substituted phenoxycarbonyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl is Noah group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 50a) venoxis1-C6alkylcarboxylic group, 51a) substituted venoxis1-C6alkylcarboxylic group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6the alkyl is of kinogruppy, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group 52a) phenylsulfonyl group, 53a) substituted phenylsulfonyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group 54a) dis1-C6alkylphosphonium, where the alkyl groups are the same or different, 55a) dis1-C6alkylphosphonium, where the alkyl groups are the same or different, 56a) N-C1-C6alkyl-N-C1-C6alkoxycarbonylmethyl, 57a) N-C1-C6alkyl-N-C1-C6alkoxycarbonyl1-C6and is colamination, 58a) dis1-C6alkylammonium, where the alkyl groups are the same or different, 59a) C3-C6cycloalkylcarbonyl group, 60a) Halogens3-C6cycloalkylcarbonyl group, 61a) C1-C6alkyls3-C6cycloalkylcarbonyl group, 62a) Halogens1-C6alkyls3-C6cycloalkylcarbonyl group, 63a) panels1-C6alkylcarboxylic group, 64a) substituted phenyls1-C6alkylcarboxylic group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 65a) panels3-C6cycloalkylcarbonyl group 6a) substituted phenyls 3-C6cycloalkylcarbonyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, 1) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 67a) C3-C6cycloalkyl1-C6alkylcarboxylic group, 68a) C1-C6alkoxyl1-C6alkylcarboxylic group, 69a) Halogens3-C6cycloalkyl1-C6alkylcarboxylic group, 70a) venoxis1-C6alkoxycarbonyl group, 71a) substituted venoxis1-C6alkoxycarbonyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1- 6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 72a) C1-C6alkylcarboxylic1-C6alkyl group, 73a) C1-C6alkylcarboxylic1-C6alkylcarboxylic group or 74a) C1-C6alkoxycarbonyl1-C6alkylcarboxylic group;

R21b is a) a hydrogen atom, 2b) halogen atom, 3b) C1-C6alkyl group, 4b) Halogens1-C6alkyl group, 5b) cyano, 6b) a hydroxy-group, 7b) C1-C6alkoxygroup, 8b) Halogens1-C6alkoxygroup, 9b) C1-C6alkoxyl1-C3alkoxygroup, 10b) Halogens1-C6alkoxyl1-C3alkoxygroup, 11b) C1-C6alkylthio1-C3alkoxygroup, 12b) Halogens 1-C6alkylthio1-C3alkoxygroup, 13b) C1-C6alkylsulfonyl1-C3alkoxygroup, 14b) Halogens1-C6alkylsulfonyl1-C3alkoxygroup, 15b) C1-C6alkylsulfonyl1-C3alkoxygroup, 16b) Halogens1-C6alkylsulfonyl1-C3alkoxygroup, 17b) mono1-C6alkylamino1-C3alkoxygroup, 18b) dis1-C6alkylamino1-C3alkoxygroup, where the alkyl groups are the same or different, 19b) C1-C6allylthiourea, 20b) Halogens1-C6allylthiourea, 21b) C1-C6alkylsulfonyl group, 22b) Halogens1-C6alkylsulfonyl group, 23b) C1-C6alkylsulfonyl group, 24b) Halogens1-C6alkylsulfonyl group, 25b) amino group, 26b) mono1-C6alkylamino, 27b) dis1-C6alkylamino, where the alkyl groups are the same or different, 28b) fenoxaprop, 29b) is substituted by fenoxaprop having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6Ala is syrupy, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 30b) phenylthiourea, 31b) is substituted by phenylthiourea having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 32b) phenylsulfinyl GRU is PU, 33b) substituted phenylsulfinyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 34b) phenylsulfonyl group, 35b) substituted phenylsulfonyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens -C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 36b) panels1-C6alkoxygroup or 37b) substituted phenyls1-C6alkoxygroup having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group;

G represents 1c) C2-C10alkyl group, 2c) Halogens2-C10alkyl group, 3c) C3-C 10alkenylphenol group, 4c) Halogens3-C10alkenylphenol group, 5c) C3-C10alkylamino group, 6c) Halogens3-C10alkylamino group, 7c) C3-C10cycloalkyl group, 8c) substituted C3-C10cycloalkyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) C1-C6alkyl groups and c) Halogens1-C6alkyl group, 9c) C3-C10cycloalkenyl group, 10c) substituted C3-C10cycloalkenyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) C1-C6alkyl groups and c) Halogens1-C6alkyl group, 11e) C3-C8cycloalkyl1-C6alkyl group or 12c) Halogens3-C8cycloalkyl1-C6alkyl group;

X may be the same or different and represent 1d) a hydrogen atom, 2d) halogen atom, 3d) cyano, 4d) of the nitrogroup, 5d) C1-C6alkyl group or 6d) Halogens1-C6alkyl group;

n is an integer from 1 to 3,

their salts and 1,3-dimethyl-5-cryptomaterial-4-carboxylic acid and its salts.

Definitions substituted pyrazolecarboxylate derivative of the formula (I) and samisen the th aniline derivative of the formula (II) of the present invention, "halogen", "C1-C6alkyl, C1-C6alkoxyl", "C2-C6alkenyl", "C2-C6quinil" or "heterocyclic group" and the like, each of the substituents has the following value.

"Halogen" or "halogen atom" means a chlorine atom, bromine atom, iodine atom or fluorine atom.

"C1-C6alkyl" represents a linear alkyl and branched chain having 1-6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 2-methylbutyl, 1-ethylpropyl, n-hexyl, 2-ethylbutyl and the like.

"C1-C6alkyl" represents a linear alkyl and branched chain having 1-8 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 2-methylbutyl, 1-ethylpropyl, n-hexyl, 2-ethylbutyl, n-heptyl, n-octyl, 2-ethylhexyl, and the like.

"C2-C10alkyl" represents a linear alkyl and branched chain having 2-10 carbon atoms, such as ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 2-methylbutyl, n-hexyl, 2-ethylbutyl, 1-ethylpropyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl and the like.

"C3-C6 cycloalkyl" is a cyclic alkyl having 3-6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.

"C3-C8cycloalkyl" is a cyclic alkyl having 3-8 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and the like.

"C3-C10cycloalkyl" is a cyclic alkyl having 3 to 10 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, cyclodecyl and the like.

"C3-C10cycloalkenyl" represents a cyclic alkenyl having 3-10 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentenyl, cyclohexenyl, cyclooctyl, cyclodecyl and the like.

"C1-C3alkoxy" represents an alkoxy, where the alkyl residue is a linear alkyl and branched chain having 1-3 carbon atoms, such as methoxy, ethoxy, propoxy, isopropoxy and the like.

"C1-C6alkoxy" represents an alkoxy, where the alkyl residue is a above "C1-C6alkyl, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, isopentylamine, neopentylene, tert-pentyloxy, 2-methylb the toxi, 1 ethylpropoxy, hexyloxy, 2-ethylbutane and the like.

"C1-C10alkoxy" represents an alkoxy, where the alkyl residue is a linear alkyl and branched chain having 1-10 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, isopentylamine, neopentylene, tert-pentyloxy, 2-methylbutoxy, 1 ethylpropoxy, hexyloxy, 2-ethylbutane, n-heptyloxy, n-octyloxy, 2-ethylhexyloxy, n-nonyloxy, n-decyloxy and the like.

"C1-C16alkoxy" represents an alkoxy, where the alkyl residue is a linear alkyl and branched chain having 1 to 16 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, isopentylamine, neopentylene, tert-pentyloxy, 2-methylbutoxy, 1 ethylpropoxy, hexyloxy, 2-ethylbutane, n-heptyloxy, n-octyloxy, 2-ethylhexyloxy, n-nonyloxy, n-decyloxy, n-undecyloxy, n-dodecyloxy, n-tridecylamine, n-tetradecane, n-pentadecane, n-hexadecylamine and the like.

"C2-C6alkenyl is alkenyl with linear and branched chain having 2 to 6 carbon atoms, which has at least one double bond, such as vinyl, 1-propenyl, allyl, 1-bout the sludge, 2-butenyl, 3-butenyl, 2-pentenyl, 2-methyl-1-propenyl, 2,4-pentadienyl, 3-hexenyl and the like.

"C3-C10alkenyl is alkenyl with linear and branched chain having 3-10 carbon atoms, which has at least one double bond, such as 1-butenyl, 2-butenyl, 3-butenyl, 2-pentenyl, 2,4-pentadienyl, 3-hexenyl, 3-heptenyl, 3-octenyl, 3-nonanol, 3-decenyl and the like.

"C2-C6quinil" is a quinil with linear and branched chain having 2 to 6 carbon atoms, which has at least one triple bond, such as ethinyl, 2-PROPYNYL, 1-butynyl, 2-butynyl, 3-butynyl, 2-pentenyl, 3-hexenyl and the like.

"C3-C10quinil" is a quinil with linear and branched chain having 3-10 carbon atoms, which has at least one triple bond, such as 1-butynyl, 2-butynyl, 3-butynyl, 2-pentenyl, 3-hexenyl, 3-heptenyl, 3-octenyl, 3-nonenal, 3-decenyl and the like.

The numbers in the "C2-C6", "C3-C10" and things like that, show the range of the number of carbon atoms, such as 2 to 6 carbon atoms and 3 to 10 carbon atoms.

In addition, the above definition can be applied to groups, which are attached to the above substituents. For example, "Halogens1-C6alkyl" means an alkyl group with whether anoy or branched chain, having 1-6 carbon atoms, which is substituted by one or more identical or different halogen atoms, such as chloromethyl, 2-chloroethyl, 2,2,2-trichloroethyl, 3-chloropropyl, 2-chloro-1,1-dimethylethyl, 1-bromo-1-methylethyl, deformity, trifluoromethyl, 2,2,2-triptorelin, perferences and the like.

"Heterocyclic group" and "heterocyclyl" represent a 5 - or 6-membered heterocyclic group having one or more heteroatoms selected from oxygen atom, sulfur atom and nitrogen atom, including, for example, pyridyloxy group, a pyridine-N-oxide group, pyrimidinyl group, follow group, tetrahydrofuryl group, thienyl group, tetrahydrocannibinol group, tetrahydropyranyloxy group, tetrahydropyranyloxy group, oxazolidinyl group, isoxazolyl group, oxadiazolyl group, thiazolidine group, isothiazolinone group, thiadiazolyl group, imidazolidinyl group, triazolyl group and pyrazolidine group.

Salt substituted pyrazolecarboxylate derivative represented by the formula (I) of the present invention includes a salt of an alkali metal (lithium, sodium, potassium and the like); salts of alkaline-earth metal (calcium, magnesium and the like); salt, ammonium salt and organic amine (methylamine, triethylamine, diethanolamine, piperidine, pyrid is on, and the like) or an acid additive salt. An acid additive salt includes, for example, carboxylate, such as acetate, propionate, oxalate, triptorelin, benzoate and the like; sulfonate such as methanesulfonate, triftorbyenzola, p-toluensulfonate and the like; a salt of an inorganic acid such as hydrochloride, sulfate, nitrate, carbonate, and the like.

In substituted pyrazolecarboxylate derivatives represented by the formula (I) of the present invention, R1preferably represents 1a) a hydrogen atom, 2a) C1-C6alkyl group, 3a) Halogens1-C6alkyl group, 4a) C1-C6alkylcarboxylic group 5a) Halogens1-C6alkylcarboxylic group 6a) C2-C6alkenylboronic group 13a) C2-C6alkenylphenol group, 17a) C1-C10alkoxyl1-C6alkyl group, 18a) Halogens1-C6alkoxyl1-C6alkyl group, 19a) C2-C6alkenylacyl1-C6alkyl group, 20a) C1-C6alkoxyl1-C6alkoxyl1-C6alkyl group, 29a) panels1-C6alkoxyl1-C6alkyl group, 30a) substituted phenyls1-C6alkoxyl1-C6alkyl group having on the ring one or more identical or different substituents selected from a) halogen atom is, b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 31a) C1-C16alkoxycarbonyl group, 32a) C1-C6alkoxyl1-C6alkoxycarbonyl group, 33a) Halogens1-C6alkoxycarbonyl group, 34a) C2-C6altneratively group, 35a) C1-C6alkylthiomethyl group 42a) panels1-C6alkyl group, 43a) substituted phenyls1-C6alkyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C 6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 44a) phenylcarbonylamino group, 45a) substituted phenylcarbonylamino group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl the school group, 46a) geterotsiklicheskikh group, 47a) substituted geterotsiklicheskikh group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 48a) phenoxycarbonyl group, 49a) substituted phenoxycarbonyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 50a) venoxis1-C6alkylcarboxylic group, 51a) substituted venoxis1-C6alkylcarboxylic group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group 52a) phenylsulfonyl group, 53a) substituted phenyls Lionello group, having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 58a) dis1-C6alkylammonium, where the alkyl groups are the same or different, 59a) C3-C6cycloalkylcarbonyl group, 61a) C1-C6alkyls3-C6cycloalkylcarbonyl group, 63a) panels1-C6alkylcarboxylic group, 64a) substituted phenyls1-C6alkylcarboxylic group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 65a) panels3-C6cycloalkylcarbonyl group, 66a) substituted phenyls3-C6cycloalkylcarbonyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (c) nitro group, (d) C1-C6alkyl groups, e) Halogens1-C6alkyl group, f) C1-C6alkoxygroup, g) Halogens1-C6alkoxygroup, h) C1-C6allylthiourea, i) Halogens1-C6allylthiourea, j) C1-C6alkylsulfonyl group, k) Halogens1-C6alkylsulfonyl group, l) C1-C6alkylsulfonyl group, m) Halogens1-C6alkylsulfonyl groups, n) mono1-C6alkylamino, o) dis1-C6alkylamino, where the alkyl groups are the same or different, and p) C1-C6alkoxycarbonyl group, 68a) C1-C6alkoxyl1-C6alkylcarboxylic group, 73a) C1-C6alkylcarboxylic1-C6alkylcarboxylic group or 74a) C1-C6alkoxycarbonyl1-C6alkylcarboxylic group, and more preferably, 1a) a hydrogen atom, 4a) C1-C6alkylcarboxylic group 5a) Halogens1-C6alkylcarboxylic group, 17a) C1-C10alkoxyl1-C6alkyl group, 18a) Halogens1-C6alkoxyl1-C6alkyl group, 31a) C1-C16alkoxycarbonyl group, 33a) Halogens1-C6alkoxycarbonyl group or 68a) C1-C6alkoxyl1-C6alkylcarboxylic group.

R2preferably represents 1b) a hydrogen atom, 2b) halogen atom, 6b) a hydroxy-group, 7b) C1-C6alkoxygroup or 8b) Halogens1-C6alkoxygroup, and more preferably, 1b) a hydrogen atom or 7b) C1-C6alkoxygroup.

G preferably represents 1c) C2-C10alkyl group, 3c) C3-C10alkenylphenol group or 11e) C3-C8cycloalkyl1-C6alkyl group, and more preferably, 1c) C2-C10alkyl group

X preferably represents 1d) a hydrogen atom, 2d) halogen atom or 5d) C1-C6alkyl group, and more preferably, 1d) hydrogen atom.

Z preferably represents an oxygen atom.

Y1preferably represents 2e) C1-C6alkyl group, 3e) Halogens1-C6alkyl group or 4e) C2-C6alkenylphenol group, and more preferably, 2e) C1-C6alkyl group.

Y2preferably represents 1f) a hydrogen atom, 2f) halogen atom, 9f) C1-C6alkyl group, 10f) Halogens1-C6alkyl group or 31f) C1-C6allylthiourea, and more preferably, 1f) a hydrogen atom, 2f) halogen atom, 9f) C1-C6alkyl group or 10) Halogens1-C6alkyl group.

m is preferably equal to 2.

In addition, the salt of the substituted aniline derivative represented by the formula (II)preferably represents an acid additive salt, including, for example, carboxylate, such as acetate, propionate, oxalate, triptorelin, benzoate and the like; sulfonate such as methanesulfonate, triftorbyenzola, p-toluensulfonate and the like; a salt of an inorganic acid such as hydrochloride, sulfate, nitrate, carbonate, and the like.

Salt of 1,3-dimethyl-5-three is torneypurta-4-carboxylic acid of the present invention includes a salt of an alkali metal (lithium, sodium, potassium and the like); a salt of alkaline earth metal (calcium, magnesium and the like); salt, ammonium salt and organic amine (methylamine, triethylamine, diethanolamine, piperidine, pyridine and the like).

Substituted pyrazolecarboxylate derivative represented by the formula (I), or an intermediate compound that is substituted aniline derivative represented by the formula (II), the present invention can have one or more asymmetric centers in the structural formula, and in addition, there may be two or more optical isomers and diastereomers. As a consequence, the present invention completely covers each optical isomer and a mixture of any of their ratio. In addition, substituted pyrazolecarboxylate derivative represented by the formula (I), the present invention can have two types of geometrical isomers derived from the double bond C-C in the structural formula. The present invention encompasses all geometric isomers and mixtures thereof at any proportion. In addition, the present invention encompasses their hydrates.

Representative methods of obtaining substituted pyrazolecarboxylate derivative represented by the formula (I), and substituted aniline derivative represented by the formula (II)as its intermediate is soedineniya, illustrated below, but the present invention should not be construed as limited by them.

The method of obtaining 1

(where G, R1, X, n, Y1, Y2and m are as defined above, and R3represents a hydrogen atom, a C1-C6alkyl group, Halogens1-C6alkyl group, phenyl group, substituted phenyl group or panels1-C4alkyl group; W represents-O-, -S - or-N(R4)-, where R4represents a hydrogen atom, a C1-C6alkyl group, Halogens1-C6alkyl group, phenyl group, substituted phenyl group or panels1-C4alkyl group, and Q represents a halogen atom or C1-C6CNS group).

Among the substituted pyrazolecarboxylate derivatives represented by the formula (I), substituted pyrazolecarboxylate derivative (I-1), where Z represents O, and R2represents a hydrogen atom, a fluorine atom or WR3where W and R3are as defined above, can be obtained by reacting an aniline derivative represented by formula (II-1)to(II-3), with halogenerator pyrazolylborate acid or ether pyrazolylborate acid represented by the formula (III), in presets is under or in the absence of a base, in an inert solvent, or by reacting an aniline derivative represented by formula (II-1)to(II-3), with pyrazolylborate acid represented by the formula (IV), in the presence of a condensing agent, in the presence or in the absence of a base in an inert solvent, and can be used any conventional methods for producing amides.

Aniline derivative represented by formula (II-2)may be obtained by reduction of an aniline derivative represented by formula (II-1), in the presence of a reducing agent, in an inert solvent.

Aniline derivative represented by formula (II-3)can be obtained by reacting an aniline derivative represented by formula (II-1), with an alcohol derivative, tilenum derived or aminoven derivative represented by the formula (V)in the presence or in the absence of a base in an inert solvent.

Formula (II-1) → formula (II-2)

An example of a reducing agent, which can be used in this reaction include metal hydrides, such as sociallyengaged, borohydride lithium, borohydride sodium, diisobutylaluminium, sodium bis-(2-methoxyethoxy)aluminiumhydride and the like, metal such as lithium, and the like, or metal salts, and the like. The amount of the reducing agent, the which can be used choose appropriately in the range from an equivalent amount to an excessive amount in relation to the aniline derivative represented by formula (II-1).

Examples of the inert solvent which can be used in this reaction and may be any, as he does not appreciably slow the progress of this reaction include 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; ethers, straight chain or cyclic, such as a simple diethyl ether, dioxane, tetrahydrofuran and the like, or dimethylsulfoxide and the like, and these inert solvents can to be used individually or in combination of two or more types.

The reaction temperature may be from room temperature to the boiling point of the inert solvent which can be used, and the reaction time may be from several minutes to 50 hours, depending on the reaction scale and reaction temperature.

After completion of the reaction, the desired compound can be isolated from the reaction mixture by conventional methods, yulaeva the connection can be subjected to cleaning using recrystallization or column chromatography, and the like, if it is necessary. The desired compound can be used at a later stage of the reaction without isolation from the reaction mixture.

Formula (II-1) → formula (II-3)

An example of a Foundation that can be used in this reaction include 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 metallocene, such as n-utility, second-utility, tert-utility and the like. The number of bases that can be used can be selected appropriately in the range from an equivalent amount to an excessive amount in relation to the aniline derivative represented by formula (II-1).

Examples of the inert solvent which can be used in this reaction and may be any, as he does not appreciably slow the progress of this reaction include aromatic hydrocarbons such as benzene, toluene, xylene and the like; alcohols such as methanol, ethanol and the like; ethers, straight chain or cyclic, such as a simple diethyl ether, 1,2-dimethoxyethane, dioxane, tetrahydrofuran and the like, and these inert solvents can be used individually or in combination of two or more VI is s.

The reaction temperature may be in the range from -70°C to the boiling point of the inert solvent which can be used, and the reaction time may be from several minutes to 50 hours, depending on the reaction scale and reaction temperature.

After completion of the reaction, the desired compound can be isolated from the reaction mixture by conventional methods, and the desired compound can be subjected to cleaning using recrystallization or column chromatography, and the like, if necessary. The desired compound can be used at a later stage of the reaction without isolation from the reaction mixture.

Formula (II-1), (II-2) or (II-3) → formula (I-1)

Examples of the condensing agent which can be used in this reaction include diethylthiophosphate (DEPC), carbonyldiimidazole (CDI), 1,3-dicyclohexylcarbodiimide (DCC), chloroformate, 2-chloro-1-methylpyridinium and the like.

As the substrate that can be used in this reaction included inorganic base or organic base, and examples of inorganic bases include alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and the like; alkali metal hydrides such as sodium hydride, potassium hydride and the like; salts selecing the metal and alcohol, such as ethoxide sodium tert-piperonyl potassium and the like; carbonates such as sodium carbonate, potassium carbonate, sodium bicarbonate and the like; and the example of organic bases include triethylamine, pyridine, DBU and the like. The number of bases that can be used can be selected within the range of an equivalent amount to an excessive amount in relation to the derived pyrazolylborate acid represented by the formula (III) or (IV).

Examples of the inert solvent which can be used in this reaction and may be any, as he does not appreciably slow the progress of this reaction include 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; ethers, straight chain or cyclic, such as a simple 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 may be used separately or in combination of two or more types.

Since this reaction is an equimolar reaction, each reagent can be used in equal molar quantities, however, any of the reagents can also be used in excess. The reaction temperature may be from room temperature to the boiling point of the inert solvent which can be used, and the reaction time may be from several minutes to 48 hours, depending on the reaction scale and reaction temperature.

After completion of the reaction, the desired compound can be isolated from the reaction mixture by conventional methods, and the desired compound can be subjected to cleaning using recrystallization or column chromatography, and the like, if necessary.

Aniline derivative represented by formula (II-1)as the starting material of this reaction, can be obtained in accordance with the production method, described in the patent of Japan JP-A-11-302233, JP-A-2001-122836 or JP-A-2006-8675.

Derived pyrazolylborate acid represented by the formula (III) or (IV)may be obtained according to several methods known in the literature (e.g., Aust. J. Chem., 1983, 36, 135-147, Synthesis, 1986, 753-755, application Japan patent JP-A-52-87168, JP-A-63-452 64, JP-A-1-106866 and the like).

The method of obtaining 2

(where G, R1, R2, X, n, Y1, Y2and m are as defined above).

Among the substituted pyrazolecarboxylate derivatives represented by the formula (I), substituted pyrazolecarboxylate derivative (1-2), where Z represents S, can be obtained by reacting anilides derivative represented by (I-1), with a reagent of Losone in accordance with the known method (Tetrahedron Lett., 21 (42), 4061 (1980)).

The method of obtaining 3

(where G, R2, X, n, Y1, Y2, m and Q are as defined above, and R1' is as defined above, except hydrogen atom).

Among the substituted pyrazolecarboxylate derivatives represented by the formula (I), substituted pyrazolecarboxylate derivative (I-4), where R1is other than a hydrogen atom can be obtained by reacting the amide derivative represented by formula (I-3)with a halide derivative or ester derivative represented by the formula (VI)in the presence or in the absence of a base in an inert solvent.

Examples of bases that can be used in this reaction include metal hydroxides such as sodium hydroxide, potassium hydroxide and the like; carbonates such as sodium carbonate, carbonate Kali is, sodium bicarbonate and the like; 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; altimetry, such as n-utility, second-utility, tert-utility and the like. The number of bases that can be used can be selected appropriately in the range from an equivalent amount to the excess amount relative to the amide derivative represented by formula (I-3).

Examples of the inert solvent which can be used in this reaction and may be any, as he does not appreciably slow the progress of this reaction include aromatic hydrocarbons such as benzene, toluene, xylene and the like; alcohols such as methanol, ethanol and the like; ethers, straight chain or cyclic, such as a simple diethyl ether, 1,2-dimethoxyethane, dioxane, tetrahydrofuran and the like; amides, such as dimethylformamide, dimethylacetamide and the like; dimethyl sulfoxide; 1,3-dimethyl-2-imidazolidinone and the like. These inert solvents may be used individually or in combination of two or more types.

The reaction temperature may be in the range from -70°C to the boiling point, and not the private solvent, which can be used, and the reaction time may be from several minutes to 50 hours, depending on the reaction scale and reaction temperature.

After completion of the reaction, the desired compound can be isolated from the reaction mixture by conventional methods, and the desired compound can be subjected to cleaning using recrystallization or column chromatography, and the like, if necessary.

The method of obtaining 4

(where G, R1, R3, X, n, Y1, Y2and m are as defined above, and q is 1 or 2).

Substituted pyrazolecarboxylate derivative represented by formula (I-6)can be obtained by reacting a sulfide derivative represented by formula (I-5), which can be obtained according to the method of obtaining 1, with an oxidizing agent in the presence of an inert solvent.

Examples of the inert solvent which can be used in this reaction include halogenated hydrocarbons such as methylene chloride, chloroform and the like; aromatic hydrocarbons such as toluene, xylene and the like; halogenated aromatic hydrocarbons such as torbenson, chlorobenzene, dichlorobenzene and the like; acids such as acetic acid and the like is; alcohols, such as methanol, ethanol, propanol and the like.

Examples of the oxidizing agent include m-peroxycarbonates acid, peracetic acid, metaperiodate potassium, hydropersulfides potassium (Oxon), hydrogen peroxide, and the like. The amount of oxidizing agent, which can be used can be selected appropriately in the range from 0.5 to 3 equivalents relative to the sulfide derivative represented by formula (I-5).

The reaction temperature may be in the range from -50°C to the boiling point of the inert solvent which can be used, and the reaction time may be from several minutes to 24 hours, depending on the reaction scale and reaction temperature.

After completion of the reaction, the desired compound can be isolated from the reaction mixture by conventional methods, and the desired compound can be subjected to cleaning using recrystallization or column chromatography, and the like, if necessary.

Specific compounds substituted pyrazolecarboxylate derivatives represented by the formula (I)depicted in tables 1 and 2, specific compounds substituted aniline derivative represented by the formula (II), illustrated in table 3, and substituted derivatives pyrazolylborate acid, p is zestawienie formula (IV), illustrated in table 4, but the present invention should not be construed as limited by them.

In the column "property" in table 1 and table 2 shows the melting temperature (°C) or refractive index (nD(°C)) and compounds described as amorphous or pasty, their data1H-NMR are shown in table 5. In the tables, "n" means normal, "i" means ISO, "t" means tertiary, "c-" means cyclo, Me means methyl group, "Et" means ethyl group, "Pr" means through the group, "Bu" means boutelou group, "Pen" means pentelow group, "Hex" means hexoloy group, "Ph" means phenyl group, "Bn" means benzyl group, "Ac" means acetyl group and "Pyr" means personilnya group.

Table 1
Formula (I-4)

(Xn=H)
No.GY1Y2mR1R2Properties
1-1EtMe 2HH72-75
1-2EtMe3,5-Me2AUH
1-3EtMe3,5-Me2HOMe129-131
1-4EtMe3,5-Me2AcOMe1,5028(25,4)
1-5EtMe3,5-Me2COEtOMe
1-6EtMe3,5-Me2CO-c-PrOMe118,8-to 121.6
1-7EtMe3,5-Me2 CH2OMeOMe
1-8EtMe3,5-Me2CH2OEtOMe1,4889(24,2)
1-9EtMe3,5-Me2COOMeOMe
1-10EtMe3,5-Me2COOEtOMe77,2-79,2
1-11EtMe3,5-Me2COO-n-PrOMe
1-12EtMe3,5-Me2COO-i-BuOMe1,4895(25,4)
1-13EtMe 3,5-Me2HOEt110-113
1-14EtMe3,5-Me2AcOEt
1-15EtMe3,5-Me2COEtOEt90-91
1-16EtMe3,5-Me2CO-c-PrOEt119-120
1-17EtMe3,5-Me2CH2OMeOEt
1-18EtMe3,5-Me2CH2OEtOEt
1-19EtMe 3,5-Me2COOMeOEt
1-20EtMe3,5-Me2COOEtOEt
1-21EtMe3,5-Me2COO-n-PrOEt
1-22EtMe3,5-Me2COO-i-BuOEt
1-23EtMe3-CF3-5-MeHH1,4768(21,8)
1-24EtMe3-CF3-5-MeAcH132-134
1-25EtMe 3-CF3-5-MeHOMe57-60
1-26EtMe3-CF3-5-MeAcOMe1,4736(24,6)
1-27EtMe3-CF3-5-MeCOEtOMe134-135
1-28EtMe3-CF3-5-MeCO-c-PrOMe1,4830(26,2)
1-29EtMe3-CF3-5-MeCH2OMeOMe
1-30EtMe3-CF3-5-MeCH2OEtOMe
1-31Et Me3-CF3-5-MeCOOMeOMe128-130
1-32EtMe3-CF3-5-MeCOOEtOMe1,4697(25,9)
1-33EtMe3-CF3-5-MeCOO-n-PrOMe
1-34EtMe3-CF3-5-MeCOO-i-BuOMe1,4681(26,2)
1-35EtMe3-CF3-5-MeHOEt142-145
1-36EtMe3-CF3-5-MeAcOEt1,4720(24,5)
1-37Et/td> Me3-CF3-5-MeCOEtOEt1,4710(26,9)
1-38EtMe3-CF3-5-Meco-c-PrOEt
1-39EtMe3-CF3-5-MeCH2OMeOEt

1-40EtMe3-CF3-5-MeCH2OEtOEt
1-41EtMe3-CF3-5-MeCOOMeOEt
1-42EtMe3-CF3-5-MeCOOEtOEt
1-43EtMe3-CF3-5-MeCOO-n-PrOEt
1-44EtMe3-CF3-5-MeCOO-i-BuOEt
1-45n-PrMe3,5-Me2HH167-168
1-46n-PrMe3,5-Me2AcH
1-47n-PrMe3,5-Me2HOMe184-185
1-48n-PrMe3,5-Me2AcOMe 1,4953(25,0)
1-49n-PrMe3,5-Me2COEtOMe1,4982(34,2)
1-50n-PrMe3,5-Me2CO-c-PrOMe
1-51n-PrMe3,5-Me2CH2OMeOMe1,4979(22,1)
1-52n-PrMe3,5-Me2CH2OEtOMeto 1.4942(22,7)
1-53n-PrMe3,5-Me2COOMeOMe1,4980(22,7)
1-54n-PrMe3,5-Me2COOEt OMe1,4952(23,0)
1-55n-PrMe3,5-Me2COO-n-PrOMe
1-56n-PrMe3,5-Me2COO-i-BuOMe1,4933(23,2)
1-57n-PrMe3,5-Me2HOEt178-179
1-58n-PrMe3,5-Me2AcOEt
1-59n-PrMe3,5-Me2COEtOEt1,4980(22,7)
1-60n-PrMe3,5-Me2CO-c-Pr OEt
1-61n-PrMe3,5-Me2CH2OMeOEt
1-62n-PrMe3,5-Me2CH2OEtOEt
1-63n-PrMe3,5-Me2COCMeOEt
1-64n-PrMe3,5-Me2COOEtOEt
1-65n-PrMe3,5-Me2COO-n-PrOEt
1-66n-PrMe3,5-Me2COO-i-Bu OEt
1-67n-PrMe3-CF3-5-MeHH131-133
1-68n-PrMe3-CF3-5-MeAcH
1-69n-PrMe3-CF3-5-MeHOMe124
1-70n-PrMe3-CF3-5-MeAcOMe1,4711(25,6)
1-71n-PrMe3-CF3-5-MeCOEtOMe1,4700(26,8)
1-72n-PrMe3-CF3-5-MeCO-c-Pr OMe1,4795(25,5)
1-73n-PrMe3-CF3-5-MeCH2OMeOMe
1-74n-PrMe3-CF3-5-MeCH2OEtOMe1,4658(26,9)
1-75n-PrMe3-CF3-5-MeCOOMeOMe126-128
1-76n-PrMe3-CF3-5-MeCOOEtOMe1,4671(26,9)
1-77n-PrMe3-CF3-5-MeCOO-n-PrOMe
1-78n-PrMe3-CF3-5-Me COO-i-BuOMe1,4645(26,9)
1-79n-PrMe3-CF3-5-MeHOEt
1-80n-PrMe3-CF3-5-MeAcOEt
1-81n-PrMe3-CF3-5-MeCOEtOEt
1-82n-PrMe3-CF3-5-MeCO-c-PrOEt
1-83n-PrMe3-CF3-5-MeCH2OMeOEt
1-84n-PrMe3-CF3-5-Me CH2OEtOEt
1-85n-PrMe3-CF3-5-MeCOOMeOEt
1-86n-PrMe3-CF3-5-MeCOOEtOEt
1-87n-PrMe3-CF3-5-MeCOO-n-PrOEt
1-88n-PrMe3-CF3-5-MeCOO-i-BuOEt
1-89n-BuMe3,5-Me2HH150-151,5
1-90n-BuMe3,5-Me2 AcH
1-91n-BuMe3,5-Me2HOMe196-197
1-92n-BuMe3,5-Me2AcOMe
1-93n-BuMe3,5-Me2HOEt
1-94n-BuMe3,5-Me2AcOEt
1-95n-BuMe3-CF3-5-MeHH83-85

H OMe
1-96n-BuMe 3-CF3-5-MeAcH
1-97n-BuMe3-CF3-5-MeHOMe
1-98n-BuMe3-CF3-5-MeAcOMe
1-99n-BuMe3-CF3-5-MeHOEt
1-100n-BuMe3-CF3-5-MeAcOEt
1-101i-BuMe3-MeHH141-144
1-102i-BuMe3-Me EtOMe1,4916(23,7)
1-103i-BuMe3-MeAcOMe1,4961(26,4)
1-104i-BuMe3-MeCOEtOMe1,4973(26,2)
1-105i-BuMe3-MeCO-c-PrOMe1,5014(25,5)
1-106i-BuMe3-MeCO(4-Me-Ph)OMeamorphous
1-107i-BuMe3-MeCO(4-NO2-Ph)OMeamorphous
1-108i-BuMe3-Me COOMeOMe95,5 of 97.8
1-109i-BuMe3-MeCOOEtOMe84,6-86,2
1-110i-BuMe3-MeCOO-n-PrOMe86,7-88,4
1-111i-BuMe3-MeCOO-i-BuOMe91,8-94,0
1-112i-BuMe3-MeCH2OMeOMe1,4919(24,0)
1-113i-BuMe3-MeCH2OEtOMe1,4920(24,4)
1-114i-BuMe3-CF3 HH172-174
1-115i-BuMe3-CF3ACH
1-116i-BuMe3-CF3HOMeamorphous
1-117i-BuMe3-CF3AcOMe
1-118i-BuMe3-CF3HOEt
1-119i-BuMe3-CF3AcOEt
1-120i-BuEt3-CF3H175-176
1-121i-BuMe5-CF3HH155-156
1-122i-BuMe5-SMeHH107-110
1-123i-BuMe3,5-Me2HH148-151
1-124i-BuMe3,5-Me2SO2(4-F-Ph)Hamorphous
1-125i-BuMe3,5-Me2ACH1,5021(22,5)
1-126i-BuMe3,5-Me2COEt H143,1-148, 8 persons
1-127i-BuMe3,5-Me2COPhH51,3-65,3
1-128i-BuMe3,5-Me2COCH2CMe3H1,4859(22,0)
1-129i-BuMe3,5-Me2CH2OEtH1,4882(23,8)
1-130i-BuMe3,5-Me2CH2O(CH2)7MeH1,4854(22,0)
1-131i-BuMe3,5-Me2CH2O(CH2)2OMeH1,4889(21,9)
1-132i-Bu3,5-Me2CH2OBnH1,5212(21,9)
1-133i-BuMe3,5-Me2COOCH2ClH121, 1million-of 124.8
1-134i-BuMe3,5-Me2COOCH2CCl3H143,1-145,6
1-135i-BuMe3,5-Me2COO(CH2)2CH2ClH117,1-121,4
1-136i-BuMe3,5-Me2COO-i-BuH122,2-138,0
1-137i-BuMe3,5-Me2COO-t-BuH39,2
1-138i-BuMe3,5-Me2COO(CH2)2OMeH1,4750(23,5)
1-139i-BuMe3,5-Me2COO(CH2)15MeH90,5 to 92.1
1-140i-BuMe3,5-Me2AcOMe1,5016(23,3)
1-141i-BuMe3,5-Me2COEtOMe1,4981(23,5)
1-142i-BuMe3,5-Me2CO-i-PrOMeof 82.5-83
1-143i-BuMe3,5-Me2COPh1,5219(23,7)
1-144i-BuMe3,5-Me2CH2OMeOMe1,4944(23,1)
1-145i-BuMe3,5-Me2CH2OEtOMe1,4892(22,2)
1-146i-BuMe3,5-Me2CH2O(CH2)2OMeOMe1,4885(25,1)
1-147i-BuMe3,5-Me2COOMeOMe1,4926(23,2)
1-148i-BuMe3,5-Me2COOEtOMe1,4894(23,2)
1-149i-BuMe 3,5-Me2COOCH2ClOMe1,4941(21,5)
1-150i-BuMe3,5-Me2COO-n-PrOMe1,4928(22,2)
1-151i-BuMe3,5-Me2COO-i-PrOMe1,4884(23,0)

1-152i-BuMe3,5-Me2COO-i-BuOMe1,4829(22,3)
1-153i-BuMe3,5-Me2COOCH2CMe3OMe1,4864(23,0)
1-154i-BuMe3,5-Me2COO(CH2)2OMeOMe 1,4959(23,0)
1-155i-BuMe3,5-Me2HOMe189-190
1-156i-BuMe3,5-Me2EtOMeamorphous
1-157i-BuMe3,5-Me2CH2CCl3OMe1,4939(22,2)
1-158i-BuMe3,5-Me2AcOEt1,4940(26,4)
1-159i-BuMe3,5-Me2COEtOEt1,4921(26,5)
1-160i-BuMe3,5-Me2CO-i-Pr OEtpasty
1-161i-BuMe3,5-Me2COPhOEt
1-162i-BuMe3,5-Me2CH2OMeOEt
1-163i-BuMe3,5-Me2CH2OEtOEt
1-164i-BuMe3,5-Me2CH2O(CH2)2OMeOEt
1-165i-BuMe3,5-Me2COOMeOEt
1-166i-BuMe3,5-Me2/td> COOEtOEt
1-167i-BuMe3,5-Me2COOCH2ClOEt
1-168i-BuMe3,5-Me2COO-n-PrOEt
1-169i-BuMe3,5-Me2COO-i-PrOEt
1-170i-BuMe3,5-Me2COO-i-BuOEt
1-171i-BuMe3,5-Me2COOCH2CMe3OEt
1-172i-BuMe 3,5-Me2COO(CH2)2OMeOEt
1-173i-BuMe3,5-Me2HOEt165-166
1-174i-BuMe3,5-Me2EtOEt
1-175i-BuMe3,5-Me2CH2CCl3OEt
1-176i-BuEt3,5-Me2HH127-128
1-177i-BuMe3,5-Me2HF136,5-137,5
1-178i-Bu Me3,5-Me2EtH1,4904(25,7)
1-179i-BuMe3-Me-5-FHH169, 5mm-171
1-180i-BuMe3-Me-5-FHOMe135-137
1-181i-BuMe3-Me-5-FEtOMe1,4825(26,0)
1-182i-BuMe3-Me-5-FAcOMe86,4
1-183i-BuMe3-Me-5-FCOPhOMeof 124.1-130, 8mm
1-184i-BuMe 3-Me-5-FCOOMeOMe64,5-80,5
1-185i-BuMe3-Me-5-FCOO-i-BuOMe1,4789(23,7)
1-186i-BuMe3-Me-5-FCOO(CH2)2OMeOMe1,4857(22,3)
1-187i-BuMe3-Me-5-FCH2OEtOMe1,4804(23,8)
1-188i-BuMe3-Me-5-ClHH160-161
1-189i-BuMe3-Me-5-ClHOMe144-146
1-190i-BuMe 3-Me-5-ClMeOMe1,4919(25,6)
1-191i-BuMe3-Me-5-ClEtOMe1,4938(26,0)
1-192i-BuMe3-Me-5-ClCH2OMeOMel.4961(26,0)
1-193i-BuMe3-Me-5-ClCH2OEtOMe1,4932(25,6)
1-194i-BuMe3-Me-5-ClCOOMeOMe1,4883(25,6)
1-195i-BuMe3-Me-5-ClCOOEtOMe1,4915(26,0)
1-196i-BuMe 3-Me-5-ClCOO-i-BuOMe1,4850(25,6)
1-197i-BuMe3-Me-5-ClCOO(CH2)2OMeOMe1,4946(26,0)
1-198i-BuMe3-Me-5-ClACOMe102,6-102,8
1-199i-BuMe3-Me-5-ClCOEtOMe101,8-104,2
1-200i-BuMe3-Me-5-ClCOPhOMe1,5210(26,0)
1-201i-BuEt3-Me-5-ClHHof 104.5-106
1-202i-BuMe 3-Me-5-IHH152-153
1-203i-BuMe3-Me-5-CF3HOMe88-89
1-204i-BuMe3-Me-5-CF3AcOMe1,4710(25,7)
1-205i-BuMe3-Me-5-CF3COOMeOMe1,4672(25,7)
1-206i-BuMe3-Me-5-CF3CH2OEtOMe1,4652(25,7)
1-207i-BuMe3-CF3-5-MeHH1,4869(23,4)

i-Butd align="center"> 3,5-Me2
1-208Me3-CF3-5-MeAcH152-152,5
1-209i-BuMe3-CF3-5-MeCOOMeH148,5-150
1-210i-BuMe3-CF3-5-MeCH2OEtH1,4623(22,8)
1-211i-BuMe3-CF3-5-MeHOMe138-139
1-212i-BuMe3-CF3-5-MeCOOMeOMe1,4729(20,7)
1-213i-BuMe3-CF3-5-MeCOOEtOMe1,4695(20,7)
1-214i-BuMe3-CF3-5-MeCOOCH2CH=CH2OMe1,4742(24,5)
1-215i-BuMe3-CF3-5-MeCOO(CH2)2MeOMe1,4685(20,7)
1-216i-BuMe3-CF3-5-MeCOO(CH2)3MeOMe1,4689(24,5)
1-217i-BuMe3-CF3-5-MeCOO-i-BuOMe1,4669(22,6)
1-218i-BuMe3-CF3-5-MeCOOPhOMe50-55
1-219i-BuMe3-CF3-5-Me 2)2OMeOMe1,4691(22,3)
1-220i-BuMe3-CF3-5-MeCOSMeOMe1,4870(24,9)
1-221i-BuMe3-CF3-5-MeCOSEtOMe1,4862(24,9)
1-222i-BuMe3-CF3-5-MeCH2OMeOMe1,4669(22,4)
1-223i-BuMe3-CF3-5-MeCH2OEtOMe108-110
1-224i-BuMe3-CF3-5-MeAcOMe1,4720(20,6)
1-225i-Bu Me3-CF3-5-MeCO-C-PrOMe1,4735(24,8)
1-226i-BuMe3-CF3-5-MeHOEt
1-227i-BuMe3-CF3-5-MeAcOEt
1-228i-BuMe3-CF3-5-ClHH136-137
1-229i-BuMe3-CF3-5-ClAcH
1-230i-BuMe3-CF3-5-ClHOMe130-132
1-231i-Bu3-CF3-5-ClAcOMe
1-232i-BuMe3-CF3-5-ClHOEt
1-233i-BuMe3-CF3-5-ClAcOEt
1-234(CH2)4MeMe3,5-Me2HH128-130
1-2 35mm(CH2)4MeMe3,5-Me2AcH
1-236(CH2)4MeMe3,5-Me2HOMe
1-237 (CH2)4MeMe3,5-Me2AcOMe
1-238(CH2)4MeMe3,5-Me2HOEt
1-239(CH2)4MeMe3,5-Me2AcOEt
1 to 240(CH2)4MeMe3-CF3-5-MeHH
1-241(CH2)4MeMe3-CF3-5-MeAcH
1-242(CH2)4MeMe3-CF3-5-MeHMe
1-243(CH2)4MeMe3-CF3-5-MeAcOMe
1-244(CH2)4MeMe3-CF3-5-MeHOEt
1-245(CH2)4MeMe3-CF3-5-MeAcOEt
1-246CH2CMe3Me3,5-Me2HH174-176
1-247CH2CMe3Me3,5-Me2AcH
1-248CH2CMe3MeHOMe
1-249CH2CMe3Me3,5-Me2AcOMe
1-250CH2CMe3Me3,5-Me2HOEt
1-251CH2CMe3Me3,5-Me2AcOEt
1-252CH2CMe3Me3-CF3-5-MeHH
1-253CH2CMe3Me3-CF3-5-MeAcH
1-254 CH2CMe3Me3-CF3-5-MeHOMe
1-255CH2CMe3Me3-CF3-5-MeAcOMe
1-256CH2CMe3Me3-CF3-5-MeHOEt
1-257CH2CMe3Me3-CF3-5-MeAcOEt
1-258CH2CH(Me)EtMe3,5-Me2HH67-70
1-259CH2CH(Me)EtMe3,5-Me2AcH
1-260CH2CH(Me)EtMe3,5-Me2HOMe158-160
1-261CH2CH(Me)EtMe3,5-Me2AcOMe
1-262CH2CH(Me)EtMe3,5-Me2HOEt
1-263CH2CH(Me)EtMe3,5-Me2AcOEt

1-264CH2CH(Me)EtMe3-CF3-5-MeHH
1-265CH2CH(Me)EtMe 3-CF3-5-MeAcH
1-266CH2CH(Me)EtMe3-CF3-5-MeHOMe143-144
1-267CH2CH(Me)EtMe3-CF3-5-MeAcOMe
1-268CH2CH(Me)EtMe3-CF3-5-MeHOEt
1-269CH2CH(Me)EtMe3-CF3-5-MeAcOEt
1-270CH2CHEt2Me3,5-Me2HH67-70
1-271 CH2CHEt2Me3,5-Me2AcH
1-272CH2CHEt2Me3,5-Me2HOMe
1-273CH2CHEt2Me3,5-Me2AcOMe
1-274CH2CHEt2Me3,5-Me2HOEt
1-275CH2CHEt2Me3,5-Me2AcOEt
1-276CH2CHEt2Me3-CF3-5-MeHH
1-277CH2CHEt2Me3-CF3-5-MeAcH
1-278CH2CHEt2Me3-CF3-5-MeHOMe
1-279CH2CHEt2Me3-CF3-5-MeAcOMe
1-280CH2CHEt2Me3-CF3-5-MeHOEt
1-281CH2CHEt2Me3-CF3-5-MeAcOEt
1-282(CH2)2CHMe2 Me3,5-Me2HH152-153
1-283(CH2)2CHMe2Me3,5-Me2AcH
1-284(CH2)2CHMe2Me3,5-Me2HOMe166-167
1-285(CH2)2CHMe2Me3,5-Me2AcOMe1,4925(21,8)
1-286(CH2)2CHMe2Me3,5-Me2HOEt
1-287(CH2)2CHMe2Me3,5-Me2Ac OEt
1-288(CH2)2CHMe2Me3-CF3-5-MeHH
1-289(CH2)2CHMe2Me3-CF3-5-MeAcH
1-290(CH2)2CHMe2Me3-CF3-5-MeHOMe138-140
1-291(CH2)2CHMe2Me3-CF3-5-MeAcOMe
1-292(CH2)2CHMe2Me3-CF3-5-MeHOEt
1-293 (CH2)2CHMe2Me3-CF3-5-MeAcOEt
1-294(CH2)7MeMe3,5-Me2HH1,5052(23,3)
1-295(CH2)7MeMe3,5-Me2AcH
1-296(CH2)7MeMe3,5-Me2HOMe
1-297(CH2)7MeMe3,5-Me2AcOMe
1-298(CH2)7MeMe3,5-Me2H OEt
1-299(CH2)7MeMe3,5-Me2AcOEt
1-300(CH2)7MeMe3-CF3-5-MeHH
1-301(CH2)7MeMe3-CF3-5-MeAcH
1-302(CH2)7MeMe3-CF3-5-MeHOMe
1-303(CH2)7MeMe3-CF3-5-MeAcOMe
1-304(CH2)7Mee 3-CF3-5-MeHOEt
1-305(CH2)7MeMe3-CF3-5-MeAcOEt
1-306n-PrMe3-Me-5-CF3HH141-143
1-307n-PrMe3-Me-5-CF3HOMe152-153
1-308n-PrMe3-Me-5-CF3AUOMe1,4688(25,6)
1-309n-PrMe3-Me-5-CF3AcH112-113
1-310i-u Me3-CF3-5-MeCH2OMeH1,4690(25,9)
1-311i-BuMe3-Me-5-FCOOCH2CH2ClOMe1,4966(24,7)
1-312i-BuMe3,5-Me2COOCH2CH2ClOMe1,5039(24,8)
1-313i-BuMe3,5-Me2COCH2CMe3OMe1,4914(24,8)
1-314i-BuMe3,5-Me2CO-c-PrOMe1,5061(24,9)
1-315i-BuMe3-CF3-5-MeCOEtH 171-173
1-316i-BuClCH2CH23,5-Me2HOMe170-171
1-317i-BuClCH2CH23,5-Me2AcOMe1,4955(24,8)
1-318i-BuMe3,5-Me2CO-n-PrOMe1,4943(24,8)
1-319i-BuMe3,5-Me2CO-t-BuOMe113-115

3,5-Me2 Metd align="center"> i-Bu 1-339 OMe 3,5-Me2
1-320i-BuMe3,5-Me2CO(4-MeO-Ph)OMe1,5198(25,3)
1-321i-BuMeCO(4-Me-Ph)OMe1,5139(25,0)
1-322i-BuMe3,5-Me2CO(4-Cl-Ph)OMe51-64
1-323n-PrMe3-Me-5-CF3COEtOMe1,4705(26,8)
1-324i-BuMe3,5-Me2CO(3-Cl-Ph)OMe1,5266(25,4)
1-325i-BuMe3,5-Me2CO(3-Me-Ph)OMe1,5182(25,5)
1-326i-BuMe3,5-Me2CO(3-MeO-Ph)OMe1,5165(26,5)
1-327i-Bu3,5-Me2CO(2-Me-Ph)OMe88-128
1-328i-BuMe3,5-Me2CO(2-Cl-Ph)OMe121-122
1-329i-BuMe3,5-Me2CO(2-MeO-Ph)OMe57-83
1-330i-BuMe3,5-Me2COCH=CH2OMe1,5088(24,5)
1-331i-BuMe3,5-Me2COCHClMeOMeamorphous
1-332i-BuMe3,5-Me2CO(3-Me-2-Pyr)OMe52-64
1-333Me3,5-Me2SNEt2OMe
1-334i-BuMe3-CF3-5-MeCO-i-PrH161-163
1-335EtMe3-CF3-5-MeCO-i-PrOMe1,4680(26,4)
1-336i-BuMe3,5-Me2CO-t-PenOMe95-96
1-337i-BuMe3,5-Me2COCH2OMeOMe1,4939(26,5)
1-338i-BuMe3,5-Me2CO(4-CF3-Ph)OMe54
i-BuMe3,5-Me2COCH2PhOMe
1-340i-BuMe3,5-Me2COCH=CMe2OMe1,5091(26,5)
1-341i-BuMe3,5-Me2COCH=CHMeOMe1,5082(26,5)
1-342i-BuMe3,5-Me2COCH2CH2COOEtOMe100-101
1-343n-PrMe3-CF3-5-MeCOOCH2CH=CH2OMe1,4728(27,0)
1-344n-PrMe3-CF3-5-MeCO-t-Bu1,4715(26,9)
1-345n-PrMe3-CF3-5-MeCO-n-PrOMe1,4660(26,8)
1-346EtMe3-CF3-5-MeCOOCH2CH2OMeOMe1,4695(26,2)
1-347EtMe3-CF3-5-MeCO-t-BuOMe1,4730(26,2)
1-348i-BuMe3,5-Me2COCMe2CH2ClOMe1,5062(26,7)
1-349i-BuMe3,5-Me2CO-c-PenOMe1,5019(26,8)
1-350i-BuCH=CH2HOMe124-130
1-351i-BuCH=CH23,5-Me2CO-i-PrOMe1,5044(25,8)
1-352i-BuMe3,5-Me2CO(2,4-Cl2-Ph)OMeto 1.5220(26,1)
1-353i-BuMe3,5-Me2CO(3,4-Cl2-Ph)OMe53
1-354n-PrMe3,5-Me2CO-i-PrOMe1,5075(25,1)
1-355n-PrMe3-CF3-5-MeCO-i-PrOMe1,4741(25,8)
1-356 EtMe3-CF3-5-MeCOOCH2CH=CH2OMe1,4781(25,9)
1-357n-PrMe3,5-Me2CO-t-BuOMe1,4888(26,0)
1-358n-PrMe3,5-Me2CO(4-Cl-Ph)OMe41
1-359EtMe3,5-Me2n-PenOMe1,4897(25,0)
1-360EtMe3,5-Me2CH2(4-F-Ph)OMe107,9
1-361EtMe3,5-Me2CO-c-BuOMe1,4939(32,1)
1-362EtMe3,5-Me2CO-i-PrOMe100,3-103,4
1-363EtMe3,5-Me2CO-s-BuOMe1,5031(22,9)
1-364EtMe3,5-Me2CO-t-BuOMe108
1-365EtMe3,5-Me2COCMe2EtOMe1,4983(20,5)
1-366EtMe3,5-Me2COCH2OMeOMe1,4958(21,6)
1-367EtMe3,5-Me2COCHEt21,4991(21,8)
1-368EtMe3,5-Me2CO-c-PenOMe1,4977(30,5)
1-369EtMe3,5-Me2CO-c-HexOMe1,4934(25,2)
1-370EtMe3,5-Me2COCH2OPhOMeamorphous
1-371EtMe3,5-Me2COCH2-t-BuOMe1,4962(32,1)
1-372EtMe3,5-Me2CO(4-CF3-Ph)OMe1,5023(32,2)
1-373EtMe35-Me 2OMe1,4211(32,0)
1-374EtMe3,5-Me2CH2OCH2CH2OMeOMe1,4892(31,0)

1-375EtMe3,5-Me2CH2O-i-PrOMe1,4855(30,2)
1-376EtMe3,5-Me2CH2O-i-BuOMe1,4849(33,2)
1-377EtMe3,5-Me2CH2O-n-PrOMe1,4982(23,1)
1-378EtMe3,5-Me2CH2O-n-Bu OMe1,4940(23,2)
1-379EtMe3,5-Me2COOCH2CCl3OMe145, 2mm-145,8
1-380EtMe3,5-Me2COO-n-PenOMe1,4960(20,2)
1-381EtMe3-CF3-5-MeCOEtH127-128
1-382EtMe3-CF3-5-MeCO-c-BuOMe1,4818(19,1)
1-383EtMe3-CF3-5-MeCO-s-BuOMe1,4701(24,4)
1-384EtMe3-CF3-5-Me COCHEt2OMe1,4724(24,3)
1-385EtMe3-CF3-5-MeCH2O-n-BuOMe1,4670(23,7)
1-386EtMe3-CF3-5-MeCH2O-i-BuOMe1,4659(21,8)
1-387EtMe3-CF3-5-MeCH2O-n-PrOMe1,4672(21,8)
1-388EtMe3-Me-5-ClHOMeRUB 127.3-128,5
1-389EtMe3-Me-5-ClCO-i-PrOMe134,1-135,4
1-390Et Me3-Me-5-ClCO-c-BuOMe136,1 is 137.2
1-391EtMe3-Me-5-ClCO-t-BuOMe108,6-110,4
1-392EtMe3-Me-5-ClCOO-i-BuOMe1,4931(32,1)
1-393EtMe3-Me-5-ClCH2O-i-PrOMe1,4884(30,5)
1-394EtMe3-Me-5-ClCH2O-n-BuOMe1,4875(29,1)
1-395EtMe3-MeHOMe183,8-185,4
1-396Et Me3-MeCO-i-PrOMeto 114.4-USD 114.9
1-397EtMe3-MeCO-c-PenOMe1,4975(31,0)
1-398EtMe3-MeCH2O-i-PrOMe1,4902(23,4)
1-399EtMe3,5-Me2CO-n-PrOEt1,4932(23,0)
1-400EtMe3,5-Me2CO-i-PrOEt80-81
1-401n-PrMe3,5-Me2COOCH2CH=CH2OMe1,4841(23,7)
1-402 n-PrMe3,5-Me2COOCH2CHEt-n-BuOMe1,4894(23,8)
1-403n-PrMe3,5-Me2COCH2OMeOMepasty
1-404n-PrMe3,5-Me2MeOMe1,4983(22,0)
1-405n-PrMe3,5-Me2EtOMe1,4970(20,0)
1-406n-PrMe3,5-Me2CH2CH=CH2OMe1,5019(23,2)
1-407n-PrMe3,5-Me2(CH2)7MeOMe/td> 1,4880(23,5)
1-408n-PrMe3-CF3-5-MeCOOMeH140-145
1-409n-PrMe3-CF3-5-MeCOOEtH129-130
1-410n-PrMe3-CF3-5-MeCOEtH140-145
1-411n-PrMe3-CF3-5-MeCO-i-PrH135-137
1-412n-PrMe3-CF3-5-MeCH2O-n-PrOMe1,4673(21,8)
1-413n-PrMe3-CF3-5-Me CH2O-t-BuOMe1,4669(21,7)
1-414i-BuMe3,5-Me2MeOMepasty
1-415i-BuMe3,5-Me2n-PrOMepasty
1-416i-BuMe3,5-Me2CH2CH=CH2OMe70-71
1-417i-BuMe3,5-Me2CH2(4-NO2-Ph)OMepasty
1-418i-BuMe3,5-Me2CH2PhOMe90-97
1-419 i-BuMe3,5-Me2CH2(4-Me-Ph)OMepasty
1-420i-BuMe3,5-Me2CH2O-n-PrOMe59-65
1-421i-BuMe3,5-Me2CH2O-n-BuOMepasty
1-422i-BuMe3,5-Me2CH2O-i-PrOMepasty
1-423i-BuMe3,5-Me2CH2O-i-BuOMe80-82
1-424i-BuMe3,5-Me2CH2O-t-Bu OMepasty
1-425i-BuMe3,5-Me2CH2O-s-BuOMepasty
1-426i-BuMe3,5-Me2CH2OCH2CF3OMepasty
1-427i-BuMe3,5-Me2CH2OCH2CH=CH2OMepasty
1-428i-BuMe3,5-Me2CH2O(CH2)7MeOMepasty
1-429i-BuMe3,5-Me2CO-c-BuOMepasty
1-430i-BuMe3,5-Me2CO-s-BuOMe106,1-107,8

amorphous
1-431i-BuMe3,5-Me2COCHEt2OMe97,2-101,8
1-432i-BuMe3,5-Me2COCMe2BrOMe93-106
1-433i-BuMe3,5-Me2CO-c-HexOMe1,5035(24,7)
1-434i-BuMe3,5-Me2CH2(2,4,6-Cl3-Ph)OMe64,2-66,7
1-435i-BuMe3,5-Me2 OMe1,4991(20,5)
1-436i-BuMe3,5-Me2COCHMeOMeOMe1,4977(20,6)
1-437i-BuMe3,5-Me2COCMe2OMeOMe1,4906(23,6)
1-438i-BuMe3,5-Me2COOPhOMe135,3-136,1
1-439i-BuMe3-Me-5-CF3COO-i-BuOMe1,4733(21,2)
1-440i-BuMe3-Me-5-CF3CO-t-BuOMe1,4745(21,2)
1-441Me3-Me-5-CF3CO-i-PrOMe1,4722(32,1)
1-442i-BuMe3-Me-5-CF3CO-c-PrOMe1,4780(32,0)
1-443i-BuMe3-CF3-5-MeCOEtOMe1,4727(24,1)
1-444i-BuMe3-CF3-5-MeCO-i-PrOMe1,4720(24,2)
1-445i-BuMe3-CF3-5-MeCH2O-n-PrOMe1,4658(22,7)
1-446i-BuMe3-CF3-5-MeCH2O-n-BuOMe1,4670(22,5)
1-447i-BuMe3-CF3-5-MeCH2O-i-BuOMe1,4625(21,9)
1-448i-BuMe3-Me-5-FCO-t-BuOMeamorphous
1-449i-BuMe3-Me-5-ClCO-i-PrOMe124-124,4
1-450i-BuMe3-Me-5-ClCO-t-BuOMe1,4860(31,4)
1-451i-BuMe3-Me-5-ClCO-c-BuOMe114-115,3
1-452i-BuMe3-Me-5-ClCOCH2OMeOMe
1-453i-BuMe3-Me-5-ClCO-c-PenOMe136,2-137
1-454i-BuMe3-Me-5-ClCH2O-n-PrOMe1,4887(31,6)
1-455i-BuMe3-Me-5-ClCH2O-i-BuOMe60,7-64,7
1-456i-BuMe3-MeCO-i-PrOMe67,3-68,2
1-457i-BuMe3-MeCO-t-BuOMeof 124.1 output reached 125.5
1-458i-BuMe3-MeCO-s-BuOMe 1,4914(32,0)
1-459i-BuMe3-MeCO-c-BuOMe83-88,6
1-460i-BuMe3-MeCO-c-PenOMe1,4990(31,7)
1-461i-BuMe3-MeCOCHEt2OMe1,4905(28,5)
1-462i-BuMe3-MeCH2O-i-PrOMe1,4817(31,7)
1-463i-BuH3,5-Me2HOMe82,8-90,5
1-464i-BuEt3,5-Me2HOMe 162-163
1-465i-BuCH2CF33,5-Me2HOMe176-177
1-466i-BuMe3,5-Me2CO-i-PrF1,4860(22,7)
1-467CH2CHMeEtMe3,5-Me2COEtOMe1,4929(20,1)
1-468CH2CHMeEtMe3,5-Me2CO-i-PrOMe1,4910(20,0)
1-469n-BuMe3,5-Me2COEtOMe1,4895(20,6)
1-470n-BuMe3,5-Me2 CO-i-PrOMe1,4835(18,9)
1-471CH2CH-c-PenMe3-CF3-5-MeHH200-201
1-472CH2CH2CHMe2Me3,5-Me2COEtOMe1,4960(20,5)
1-473CH2CH2CHMe2Me3,5-Me2CO-i-PrOMethen 1.4950(21,6)
1-474Eti-Pr3,5-Me2HOEt173-174
1-475Eti-Pr3,5-Me2AcOEt88-89
1-476Et Me3,5-Me2HO-n-Pr104-105
1-477EtMe3,5-Me2CO-n-PrO-n-Pr1,4833(33,0)
1-478EtMe3,5-Me2CO-i-PrO-n-Pr1,4919(33,0)
1-479EtMe3,5-Me2CO-t-BuO-n-Pr1,4848(32,0)
1-480EtMe3,5-Me2CH2OEtO-n-Pr1,4729(23,5)

1-481EtMe3-I-5-MeHH134-135
1-482EtMe3,5-Me2COCHMeCOEtOEt
1-483n-PrMe3,5-Me2CO-n-PrOMe1,4959(31,2)
1-484n-PrMe3,5-Me2CO-s-BuOMe1,4960(32,3)
1-485n-PrMe3,5-Me2CO-c-PenOMe1,4880(29,0)
1-486n-PrMe3,5-Me2CH2O-n-PrOMe1,4869(28,0)
1-487n-PrMe3,5-Me2CH2O-i-Pr OMe1,4819(29,3)
1-488n-PrMe3-Me-5-ClHOMe135,4-139,0
1-489n-PrMe3-Me-5-ClCO-i-PrOMe128,1-128,2
1-490n-PrMe3-Me-5-ClCO-s-BuOMe99,2-99,7
1-491n-PrMe3-Me-5-ClCO-c-PrOMe123,0-123,9
1-492n-PrMe3-Me-5-ClCO-c-PenOMe141,7-142,1
1-493n-PrMe3-Me-5-ClCH2OEt OMe1,4954(20,7)
1-494n-PrMe3-I-5-MeHH183-185
1-495n-PrMe3-MeHOMe146,8-147,0
1-496n-PrMe3-MeCO-i-PrOMe61,6-62,9
1-497n-PrMe3-MeCO-s-BuOMe1,4960(22,2)
1-498n-PrMe3-MeCO-c-PenOMe1,4991(22,1).
1-499n-PrMe3-MeCH2O-n-PrOMe 1,4864(22,8)
1-500n-PrMe3-MeCH2O-i-PrOMe1,4863(22,4)
1-501n-PrMe3,5-Me2CO-n-PrOEt1,4892(22,7)
1-502n-PrMe3,5-Me2CO-i-PrOEt1,4910(22,8)
1-503n-PrMe3,5-Me2HO-n-Pr158-159,5
1-504n-PrMe3,5-Me2COEtO-n-Pr1,4975(20,5)
1-505n-PrMe3,5-Me2CO-n-Pr O-n-Pr1,4940(20,5)
1-506n-PrMe3,5-Me2CO-i-PrO-n-Pr1,4960(20,6)
1-507i-BuCH2CF33,5-Me2COEtOMe137-138
1-508i-BuCH2CF33,5-Me2CO-i-PrOMe
1-509i-Bui-Pr3,5-Me2HOMe166-167
1-510i-Bui-Pr3,5-Me2CO-i-PrOMe107-108
1-511i-BuMe3-Me-5-C HF143,2-144,7
1-512i-BuMe3-Me-5-ClCO-i-PrF1,4888(23,0)
1-513i-BuMe3-Cl-5-MeHOMe153-161
1-514i-BuMe3-Cl-5-MeCO-i-PrOMepasty
1-515i-BuMe3-Cl-5-MeCH2O-i-PrOMepasty
1-516i-BuMe3-Cl-5-MeCOOMeOMeamorphous
1-517i-BuMeHOMe172-174
1-518i-BuMe3-Br-5-MeCO-i-PrOMepasty
1-519i-BuMe3-Br-5-MeCH2O-i-PrOMepasty
1-520i-BuMe3-I-5-MeHH178-183
1-521i-BuMe3-Br-5-MeCOOMeOMepasty
1-522i-BuMe3-I-5-MeHOMeamorphous
1-523i-BuMe 3-I-5-MeCOOMeOMepasty
1-524i-BuMe3-I-5-MeCO-i-PrOMepasty
1-525i-BuMe3-I-5-MeCH2OEtOMe100-103
1-526i-BuMe3-I-5-MeCH2O-i-PrOMe100-102
1-527i-BuMe3,5-Me2CH2CH=CMe2OMe81-83
1-528CH=CMe2Me3,5-Me2HOMe
1-529i-Bu Me5-CF3HOMe170
1-530i-BuMe5-CF3CO-i-PrOMe1,4680(22,8)
1-531i-BuEt3,5-Me2CO-i-PrOMe1,4913(23,0)
1-532CH=CMe2Me3,5-Me2CO-i-PrOMe

1-541
1-533i-BuMe3,5-Me2CO-n-PrOEt1,4870(22,5)
1-534i-BuMe3,5-Me2HO-n-Pr 138-139
1-535i-BuMe3-IHOMe210-218
1-536i-BuMe3-BrHOMe203
1-537i-BuMe3-ClHOMe174-182
1-538i-BuMe3,5-Cl2HOMe132
1-539i-BuMe3-1CO-i-PrOMepasty
1-540i-BuMe3-BrCO-i-PrOMepasty
i-BuMe3-ClCO-i-PrOMepasty
1-542i-BuMe3-CF3CO-i-PrOMepasty
1-543i-BuMe3,5-Cl2CO-i-PrOMe113-114
1-544i-BuMe3,5-Me2Famorphous
1-545i-BuMe3,5-Me2Famorphous
1-546i-BuMe3,5-Me2 OMe150,4-151,2
1-547i-BuMe3,5-Me2CH2OAcOMe94-95
1-548i-BuMe3,5-Me2CH2OC(=O)EtOMe99
1-549i-BuMe3,5-Me2CH2OC(O)-i-PrOMe112
1-550i-BuMe3,5-Me2COSMeOMe
1-551i-BuMe3,5-Me2COSEtOMe

Table 2
Faure is ula (I-4)

(Y1=Me)
No.GXnY2mR1R2Properties
2-1Et6-Me3,5-Me2HH
2-2Et6-Me3,5-Me2AcH
2-3Et6-Me3,5-Me2HOMe
2-4Et6-Me3,5-Me2AcOMe
2-5Et6-Me 3,5-Me2HOEt
2-6Et6-Me3,5-Me2AcOEt
2-7Et6-Me3-CF3-5-MeHH
2-8Et6-Me3-CF3-5-MeAcH
2-9Et6-Me3-CF3-5-MeHOMe
2-10Et6-Me3-CF3-5-MeAcOMe
2-11Et6-Me3-CF3-5-Me HOEt
2-12Et6-Me3-CF3-5-MeAcOEt
2-13n-Pr6-Me3,5-Me2HH128-131
2-14n-Pr6-Me3,5-Me2AcH
2-15n-Pr6-Me3,5-Me2HOMe132-134
2-16n-Pr6-Me3,5-Me2AcOMe1,4905(25,9)

2-17n-Pr 6-Me3,5-Me2HOEt154-155
2-18n-Pr6-Me3,5-Me2AcOEt
2-19n-Pr6-Me3-CF3-5-MeHH
2-20n-Pr6-Me3-CF3-5-MeAcH
2-21n-Pr6-Me3-CF3-5-MeHOMe104-106
2-22n-Pr6-Me3-CF3-5-MeAcOMe1,4751(26,7)
2-23n-Pr 6-Me3-CF3-5-MeHOEt152-153
2-24n-Pr6-Me3-CF3-5-MeAcOEt
2-25n-Pr6-Me3-Me-5-ClHOMe127-128,5
2-26n-Pr6-Me3-CF3-5-MeCOEtOMe151-152
2-27i-Bu6-Cl3,5-Me2HOMe106-109
2-28i-Bu6-Cl3,5-Me2AcOMeamorphous
2-29Et 6-Me3,5-Me2CO-c-PrOMe138-140
2-30Et6-Me3,5-Me2COEtOMe132-134
2-31Et6-Me3-CF3-5-MeCO-n-PrOMe1,4960(26,6)
2-32n-Pr6-Me3-CF3-5-MeCOOMeOMe165-166
2-33i-Bu6-Me3,5-Me2HOMe126-127
2-34n-Pr6-Me3,5-Me2CO-i-PrOMe1,4955(33,5)
2-35 n-Pr6-Me3,5-Me2CO-t-BuOMe128,5-130,2
2-36n-Pr6-Me3,5-Me2COCHEt2OMe1,4918(32,6)
2-37n-Pr6-Me3,5-Me2COO-i-BuOMe1,4870(30,1)
2-38i-Bu6-Me3,5-Me2COEtOMeamorphous
2-39Et6-Me3,5-Me2CO-i-PrOMe1,4952(32,0)
2-40n-Pr6-Me3-MeHOMeamorphous
2-41n-Pr6-Me3-MeCO-i-PrOMepasty
2-42n-Pr6-Me3,5-Me2CO-i-PrOEt111-112
2-43i-Bu6-Me3,5-Me2CO-i-PrOMe38-42
2-44n-Pr6-Me3-CF3-5-MeCO-i-PrOMe155
2-45i-Bu6-Me3-CF3-5-MeHOMe68-70
2-46n-Pr6-Me3,5-Me2HOH192-195 (in Russian)

Table 3
Formula (II)

(R1=H)
NoGXnR21H-NMR[CDCl3/TMS, δ value (ppm)]
3-1n-Pr6-MeFto 7.09 (s, 1H), is 6.54 (s, 1H), 3,76 (users, 2H), 2.63 in (m, 2H), 2.13 and (s, 3H), 1,58 (m, 2H), of 0.96 (t, 3H)
3-2n-Pr6-MeHto 7.18 (s, 1H), is 6.54 (s, 1H), 4,45-4,20 (user., 2H), 4,27 (m, 1H), 2,50 (DD, 2H), and 2.14 (s, 3H), of 1.57 (m, 2H), and 0.98 (t, 3H)
3-3n-Pr6-MeOMe7,10 (s, 1H), 6,66 (s, 1H), 3.72 points users, 2H), 3,42 (s, 3H), 2,84 (m, 2H), and 2.14 (s, 3H), of 1.61 (m, 2H), and 1.00 (t, 3H)
3-4Et6-MeFto 7.09 (s, 1H), 6,56 (s, 1H), 3,78 (users, 2H), 2,71 (m, 2H), and 2.14 (s, 3H), 1,19 (dt, 3H)
3-5Et 6-MeOMe7,10 (s, 1H), of 6.68 (s, 1H), 3,75 (users, 2H), 3,41 (s, 3H), 2.91 in (DD, 2H), of 2.15 (s, 3H), 1,22 (t, 3H)
3-6EtHO-n-Pr7,22 (d, 1H), to 6.67 (d, 1H), of 6.52 (DD, 1H), 3,80 (user., 2H), 3.46 in (t, 2H), 2,92 (DD, 2H), 1.69 in (DD, 2H), 1,21 (t, 3H), were 0.94 (t, 3H)
3-7n-PrHO-n-Pr7,22 (d, 1H), 6,66 (d, 1H), 6,51 (DD, 1H), 3,78 (user., 2H), 3,47 (t, 2H), 2,85 (m, 2H), 1.70 to (DD, 2H), 1,60 (m, 2H), and 1.00 (t, 3H), were 0.94 (t, 3H)
3-8i-BuHO-n-Prfrom 7.24 (d, 1H), 6,70 (d, 1H), 6,53 (DD, 1H), 3,79 (users, 2H), 3,47 (t, 2H), 2,81 (d, 2H), 2,10 (m, 1H), 1,70 (m, 2H), of 0.95 (t, 3H), of 0.91 (d, 6H)

Table 4
Formula (IV)
NoY1Y2mMelting point (°C)
4-1Me3-Me-5-CF3 124-125,5

Table 5
No.1H-NMR[CDCl3/MS, δ value (ppm)]
1-106to 7.61 (d, 2H), 7,52 (d, 1H), 7,17 (m, 4H), 7,11 (m, 1H), 3,69 (s, 3H), 3,47(s, 3H), 2,86(d, 2H), 2,39 (s, 3H), is 2.37 (s, 3H), 1,96 (m, 1H), 0,73 (d, 6H)
1-107of 8.27 (d, 2H), 7,83 (d, 2H), to 7.59 (d, 1H), 7,22 (d, 1H), 7,17 (m, 1H), 6,97 (s, 1H), 3,66 (s, 3H), 3,51 (s, 3H), 2.91 in (d, 2H), a 2.36(s, 3H), of 1.97 (m, 1H), of 0.77 (d, 6H)
1-116of 8.04 (s, 1H), 7,73 (user., 1H), 7,72 (d, 1H), 7,50 (d, 1H), 7,43 (DD, 1H), 4,01 (s, 3H), 3,47 (s, 3H), of 2.93 (d, 2H), of 2.21 (m, 1H), were 0.94 (d, 6H)
1-1247,80 (DD, 2H), 7,49 (d, 1H), 7,13 (DD, 2H), 7,02 (DD, 1H), 6.89 in (d, 1H), 4,40-or 4.31 (m, 1H), only 3.57 (s, 3H), 2,42 (d, 2H), 2,28 (s, 3H), 2,22 (s, 3H), 1.70 to to 1.59 (m, 1H), 0,78 (d, 6H)
1-1567,41 (d, 1H), 7,01(DD, 1H), of 6.96 (d, 1H), 3,98 (DD, 2H), of 3.56 (s, 3H), 3,44(s, 3H), and 2.79(d, 2H), 2.06 to (s, 3H), from 2.00 (s, 3H), of 1.86 (m, 1H), 1,25 (DD, 3H), 0.74 and (d, 6H)
1-1607,47 (d, 1H), 7,16-7,05 (m, 2H), to 3.67 (s, 3H), of 3.60 (DD, 2H), 3.04 from (m, 1H), 2,88 (d, 2H), is 2.37 (s, 3H), of 2.25 (s, 3H), of 1.97 (m, 1H), 1,31 (t, 3H), 1.26 in (d, 6H), of 0.77 (d, 6H)
1-331of 7.48 (d, 1H), 7,10 (d, 1H), was 7.08 (s, 1H), 5,11 (kV, 1H), to 3.64 (s, 3H), of 3.45 (s, 3H), 2,96 (DD, 1H), 2,74 (the d, 1H), 2,31 (s, 3H), 2,24 (s, 3H), of 1.92 (m, 1H), 1.77 in (d, 3H), from 0.84 (d, 3H), of 0.65 (d, 3H)
1-3707,41 (d, 1H), 7,28 (m, 2H), was 7.08 (d, 1H), 6,98 (m, 2H), 6,84 (m, 2H), to 4.98 (s, 2H), 3,63 (s, 3H), 3,40 (s, 3H), 2,96 (kV, 2H), 2,18 (s, 3H), and 2.14 (s, 3H), of 1.26 (t, 3H)
1-403the 7.43 (d, 1H), 7,14 (d, 1H), 7,18 (m, 1H), 4,32 (s, 2H), 3,66 (s, 3H), 3.43 points (s, 3H), 3,39 (s, 3H), of 2.92 (m, 2H), 2,31 (s, 3H), of 2.23 (s, 3H)and 1.51 (m, 2H), were 0.94 (t, 3H)
1-4147,41 (d, 1H), 7,01 (m, 2H), to 3.58 (s, 3H), of 3.48 (s, 3H), 3,44 (s, 3H), and 2.79 (d, 2H), 2.06 to (s, 3H), from 2.00 (s, 3H), of 1.85 (m, 1H), 0,76 (d, 6H)
1-4157,39 (d, 1H), 7,00 (DD, 1H), 6,97 (d, 1H), 3,88 (m, 2H), of 3.56 (s, 3H), 3,44 (s, 3H), 2,78 (d, 2H), 2.05 is (s, 3H), from 2.00 (s, 3H), of 1.84 (m, 1H), of 1.66 (m, 2H), of 0.95 (t, 3H), 0.75 in (d, 6H)
1-4178,18 (d, 2H), 7,50 (d, 2H), 7,38 (d, 1H), 6,95 (DD, 1H), to 6.88 (d, 1H), 5,22 (s, 2H), to 3.58 (s, 3H), 3,41 (s, 3H), 2,73 (d, 2H), 2,08 (s, 3H), of 1.99 (s, 3H), at 1.73 (m, 1H), 0,70 (d, 6H)
1-4197,33 (d, 1H), 7.23 percent (d, 2H), 6,93 (DD, 1H), 6.89 in (d, 1H), 6,83 (d, 2H), is 5.06 (s, 2H), 3,79 (s, 3H), of 3.56 (s, 3H), 3,40 (s, 3H), 2,73 (d, 2H), 2.05 is (s, 3H), a 2.01 (s, 3H), of 1.74 (m, 1H), 0,70 (d, 6H)
1-4217,40 (d, 1H), 7,16 (m, 2H), and 5.30 (s, 2H), 3,61 (t, 2H)and 3.59 (s, 3H), 3.43 points (s, 3H), 2,80 (d, 2H), 2,09 (s, 3H), 2,04 (s, 3H), of 1.87 (m, 1H), 1,59 (m, 2H), 1,37 (m, 2H), of 0.91 (t, 3H), from 0.76 (d, 6H)
1-4227,39 (d, 1H), 7,18 (m, 2H), 5,31 (s, 2H), 3,91 (m, 1H)and 3.59 (s, 3H), 3.43 points (who, 3H), 2,80 (d, 2H), 2,08 (s, 3H), 2,04 (s, 3H), of 1.87 (m, 1H), 1,22 (d, 6H), of 0.77 (d, 6H)
1-4247,39 (d, 1H), 7.23 percent (m, 2H), 5,23 (s, 2H), to 3.58 (s, 3H), 3.43 points (s, 3H), 2,80 (d, 2H), 2,07 (s, 6H), 1,89 (m, 1H), 1.26 in (,9H), to 0.78 (d, 6H)
1-4257,39 (d, 1H), 7,17 (m, 2H), 5,43 (d, 1H), 5,22 (d, 1H), 3,68 (m, 1H)and 3.59 (s, 3H), 3.43 points (s, 3H), 2,80 (d, 2H), 2,08 (s, 3H), 2,04 (s, 3H), of 1.87 (m, 1H), 1,46-to 1.63 (m, 2H), 1,20 (d, 3H), of 0.89 (t, 3H), 0,77 (DD, 6H)
1-4267,42 (d, 1H), 7,10 (m, 2H), 5,43 (s, H)to 4.14 (q, 2H), to 3.58 (s, 3H), 3,44 (s, 3H), 2,80 (d, 2H), 2.05 is(s, 3H), a 2.01 (s, 3H), of 1.85 (m, 1H), 0,76 (d, 6H)
1-4277,40 (d, 1H), 7,17 (DD, 1H), 7,13 (d, 1H), by 5.87 is 5.98 (m, 1H), 5,32 (s, 2H), from 5.29 (DD, 1H), 5,20 (DD, 1H), 4.16 the (d, 2H)and 3.59 (s, 3H), 3,44 (s, 3H), 2,80 (d, 2H), 2,09 (s, 3H), 2,04 (s, 3H), of 1.87 (m, 1H), 0,76 (d, 6H)
1-4287,39 (d, 1H), 7,15 (m, 2H), and 5.30 (s, 2H), 3,60 (t, 2H)and 3.59 (s, 3H), 3.43 points (s, 3H), 2,80 (d, 2H), 2,09 (s, 3H), 2,04 (s, 3H), of 1.88 (m, 1H), 1,60 (m, 2H), 1.27mm (m, 10H)to 0.88 (t, 3H), of 0.77 (d, 6H)
1-4297,49 (d, 1H), 7,12 (d, 1H), was 7.08 (DD, 1H), 3,68 (s, 3H), 3.46 in (m, 1H), 3.46 in (s, 3H), 2,88 (d, 2H), 2.40 a (m, 2H), 2,35 (s, 3H), of 2.25 (s, 3H), 1,84-2,11 (m, 5H), to 0.80 (d, 6H)
1-4487,49 (d, 1H), 7,06 (d, 1H), 6,98 (m, 1H), to 3.64 (s, 3H), 3,47 (s, 3H), 2,86 (d, 2H), 2,39 (s, 3H), of 1.95 (m, 1H), to 1.38 (s, 9H), from 0.76 (d, 6H)
1-4527,49 (d, 1H), 7,18 (d, 1H), 7,13 (m, 1H), or 4.31 (s, 2H), 3,71 (s, H), of 3.46 (s, 3H), 3,42(s, 3H), 2,88 (d, 2H), 2,32 (s, 3H), 2,03 (m, 1H), of 0.79 (d, 6H)
1-5147,53 (d, 1H), 7,27 (d, 1H), 7,16 (DD, 1H), and 3.72 (s, 3H), of 3.48 (s, 3H), of 2.92 (d, 2H), 2,88 (m, 1H), 2,43 (s, 3H), 2,07 (m, 1H), 1,21 (d, 6H), is 0.84 (d, 6H)
1-5157,41 (d, 1H), 7,21 (s, 1H), 7,19 (d, 1H), 5,28 (s, 2H), 3,92 (m, 1H), 3,63 (s, 3H), 3,44 (s, 3H), 2,82 (d, 2H), 2,19 (s, 3H), of 1.94 (m, 1H), 1,21 (d, 6H), of 0.79 (d, 6H)
1-516at 7.55 (d, 1H), 7,32 (d, 1H), 7,16 (DD, 1H), 3,79 (s, 3H), 3,76 (s, 3H), 3,49 (s, 3H), 2,94 (d, 2H), 2,47 (s, 3H), and 2.14 (m, 1H), to 0.92 (d, 6H)
1-5187,53 (d, 1H), 7,28 (d, 1H), 7,18 (DD, 1H) 3,74 (s, 3H), 3,47 (s, 3H), of 2.92 (m, 1H), 2.91 in (d, 2H), 2,42 (s, 3H), 2,07 (m, 1H), of 1.23 (d, 6H), is 0.84 (d, 6H)
1-5197,42 (d, 1H), 7,22 (d, 1H), 7,21 (s, 1H), 5,28 (with,2H), 3,94 (m, 1H), 3,63 (s, 3H), 3,44 (s, 3H), 2,82 (d, 2H), and 2.14 (s, 3H), of 1.95 (m, 1H), 1,21 (d, 6H), of 0.79 (d, 6H)
1-5217,56 (d, 1H), 7,35 (d, 1H), 7,19 (DD, 1H), 3,81 (s, 3H), 3,76 (s, 3H), 3,50 (s, 3H), 2,94 (d, 2H), 2,47 (s, 3H), and 2.14 (m, 1H), to 0.92 (d, 6H)
1-5228,17 (user., 1H), 7,78 (d, 1H), 7,47-7,53 (m, 2H), of 3.84 (s, 3H), 3,47 (s, 3H), of 2.93 (d, 2H), 2,62 (s, 3H), 2,24 (m, 1H), of 0.95 (d, 6H)
1-523EUR 7.57 (d, 1H), 7,39 (d, 1H), 7,22 (DD, 1H), 3,84 (s, 3H), 3,76 (s, 3H), 3,50 (s, 3H), 2.95 and (d, 2H), 2,46 (s, 3H), of 2.15 (m, 1H), to 0.92 (d, 6H)
1-5247,51 (d, 1H), 7,27 (d, 1H), 7,20 (DD, 1H), 3,74 (s, 3H), 3.46 in (s, 3H), 2,99 (m, 1H), 2,90 (d, 2H), is 2.37 (s, 3H), 2,07 (m, 1H), 1.26 in (d, 6H), of 0.82 (d, 6H)
1-539at 7.55 (d, 1H), 7,16 (d, 1H), 7,11 (DD, 1H), 6.87 in (s, 1H), of 3.73 (s, 3H), of 3.48 (s, 3H), and 3.31 (m, 1H), 2,89 (d, 2H), 2,04 (m, 1H), 1.27mm (d, 6H), of 0.79 (d, 6H)
1-540at 7.55 (d, 1H), 7,20 (m, 1H), 7,12 (DD, 1H), 7,05 (s, 1H), and 3.72 (s, 3H), 3,49 (s, 3H), up 3.22 (m, 1H), 2,90 (d, 2H), 2.05 is (m, 1H), 1.26 in (d, 6H), 0,81 (d, 6H)
1-5417,56 (d, 1H), 7,21 (d, 1H), 7,15 (s, 1H), 7,12 (DD, 1H), and 3.72 (s, 3H), 3,49 (s, 3H), 3,17 (m, 1H), 2.91 in (d, 2H), 2.05 is (m, 1H), 1,25 (d, 6H), of 0.82 (d, 6H)
1-542EUR 7.57 (d, 1H), 7,17 (d, 1H), to 7.09 (DD, 1H), 7,06 (s, 1H), of 3.78 (s, 3H), 3,49 (s, 3H), 3,26 (m, 1H), 2,90 (d, 2H), 2,03 (m, 1H), 1,24 (d, 6H), to 0.78 (d, 6H)
1-5447,51 (d, 1H), 7,16 (m, 1H), 6,97 (d, 1H), 3,82 (s, 3H), of 3.65 (s, 3H), 2.63 in (t, 2H), and 2.27 (s, 3H), 2,24 (s, 3H), 2,10 (s, 3H), from 2.00 (s, 3H), 1,67 (m, 1H), 0,81 (d, 6H)
1-5457,47 (d, 1H), 7,34(d, 1H), 7,11 (m, 1H), 6,94(d, 1H), 6,86 (d, 1H), to 3.67(s, 3H), 2,60(t, 2H), of 2.51(s, 3H), of 2.38 (s, 3H), of 2.28 (s, 3H), at 1.73 (m, 1H), 0.75 in (d, 6H)
2-28a 7.62 (s, 1H), 7,25 (s, 1H), 3,71 (s, 3H), 3,50 (s, 3H), 2,88 (d, 2H), of 2.38 (s, 3H), 2,32 (s, 3H), 2,24 (s, 3H), 2,02 (m, 1H), of 0.85 (d, 6H)
2-387,41 (s, 1H), 7,12 (s, 1H), and 3.72 (s, 3H), of 3.48 (s, 3H), 2,88 (d, 2H), of 2.38 (s, 3H), of 2.30 (s, 3H), 2,24 (s, 3H), 2.40 a-2,30 (m, 2H), 2,04 (m, 1H), 1,4 (t, 3H), 0,85 (who, 6H)
2-40compared to 8.26 (s, 1H), 7,82 (s, 1H), 7,27 (user., 2H), 3,90 (s, 3H), of 3.45 (s, 3H), 2.95 and (m, 2H), 2.57 m (s, 3H), 2,32 (s, 3H), 1,71 (m, 2H), of 1.02 (t, 3H)
2-417,37 (s, 1H), 7,10 (s, 1H), 6.30-in (s, 1H)and 3.59 (s, 3H), 3,47 (s, 3H), 3.43 points (m, 1H), 2,92 (user., 2H), 2,48 (s, 3H), 2,17 (s, 3H), 1.55V (user. 2H), 1.28 (in d, 6H), were 0.94 (t, 3H)

Insecticides or acaricides for agriculture containing substituted pyrazolecarboxylate derivative represented by the formula (I)or salt of the present invention as an active ingredient are useful for the control of various insect pests such as insect pests for agriculture, harmful insects to stored grain, bad sanitary insects, nematodes and the like, which are harmful neobluchennuyu rice, fruit trees, plants other crops, flowers and ornamental plants, and the like. They have a significant insecticidal effect, for example, LEPIDOPTERA, including species of fruit trees (Adoxophes orana fasciata), a small tea tortrix (Adoxophyes sp.), the moth Manchu Codling (Grapholita inopinata), tortrix Oriental peach (Grapholita molesta), soybean moth (Leguminivoraglycinivorella), the mulberry moth (Olethreutes mori), the tea tortrix (Caloptiliathevivora/u> ), Caloptilia sp. (Caloptilia zachrysa), Apple leaf miner moth (Phy Honor yet er ringonie11a), ermine moth (Spulerrina astaurota), replica (Piers rapae crucivora), the leafroller caterpillar-Packed tobacco (Heliothis sp.), Codling moth (Laspey resia pomonella)the cabbage moth (Plutella xylostella), cane moth brown (Argyresthia conjugella), cane moth peach (Carposina niponensis), rice plavica (Chilo_ suppressalis), rice moth (Cnaphalocrocis medinalis), Ognevka chocolate (Ephestiaelutella), the mulberry Ognevka (Glyphodes pyloalis), stableboy rice Ognevka (Scirpophaga incertulas), Tolstoganova rice (Parnara guttata), rice well (Pseudaletia separata), Ognevka pink (Sesamia inferens), well litura (Spodoptera litura), well small (Spodoptera exiguaand the like;

HEMIPTERA, including Cicada restitutional (Macrosteles fascifrons), spring rice Cicada (Nephotettix cincticepts), brown rice Cicada (Nilaparvata lugens), white-backed rice Cicada (Sogatellafurcifera),Eastern listblock (Diaphorina citri), whiteflies striped (Aleurolibustaonabae), the tobacco whitefly (Bemisia tabaci), the greenhouse whitefly (Trialeurodes vaporariorum), mustard aphid leaf (Lipaphiserysimi), green peach aphid (Myzuspersicae),) wax (Ceroplastes ceriferus), pulvinaria citrus (Pulvinaria aurantii), San Jose scale Japanese camphor (Pseudaonidia duplex), California San Jose scale (Corastockaspis perniciosa), East citrus San Jose scale (Unaspisyanonensisand the like;

TYLENCHIDA, including hrusica brilliantly red (Anomala rufocuprea), Japanese beetle (Popilliajaponica), tobacco grinder small (Lasioderma serricorne), Gravograph dark brown (Lyctus brunneus), spotted ladybug (Epilachnavigintiotopunctata), Chinese weevil (Callosobruchus chinensis), vegetable weevil (Listroderescostirostris), maize weevil (Sitophilus zeamais), weevil-of cotton pollen beetle (Anthonomus grandis), rice weevil water (Lissorhoptrus oryzophilus), leaf pumpkin (Aulacophora femoralis), leaf rice (Ouleraa oryzae), beetle-Blasco striped (Phyllotreta striolata), big pine beetle (Tomicus piniperda), the Colorado potato beetle (Leptinotarsa decemlineata), the bean weevil Mexican (Epilachna varivestis), corn beetles (Diabrotica sp.and the like;

DIPTERA, including melon fly (Dacus(Zeugodacus)cucurbitae), fly Oriental fruit (Dacus(Bactrocera) dorsalis), rice leaf miner moth (Agnomyza oryzae), onion fly (Delia antiqua), fly sprout (Delia platura), Midge (Asphondylia sp.and the like;

TYLENCHIDA, including root nematode (Pratylenchus sp.), potato cyst nematodes (Globodera rostochiensis), root gall nematodes (Meloidogyne sp.), citrus nematodes (Tylenchulus semipenetrans), Aphelenchus sp. (Aphelenchus avenae), crisantemo Nemat the remote control ( Aphelenchoides ritzemabosiand the like; and

ACARINA, including citrus red mite (Panonychuscitri), red fruit mite (Panonychus ulna), red spider mite (Tetranychus cinnabarinus), tick Cansave (Tetranychus Kanzawai Kishida), Clasica spider bimaculated (Tetranychus urticae Koch), red tea gall mite (Acaphylla theae), red citrus gall mite (Aculopspelekassi), false the red Clasica (Calacarus carinatus), pear gall mite (Epitrimerus pyri), and the like.

Substituted pyrazolecarboxylate derivative represented by the formula (I)or its salts of the present invention is preferably used as insecticides or acaricides for agriculture. However, the connection shows excellent controlling effect against harmful insects, such as insect pests of forest and timber insects for livestock, sanitary insect pests, and the like, and can be used as agents for combating pests in a wide variety of areas. Examples of pests include: Tabanidae such asTabanus rufidens Bigot; Muscidae such as the fly room (Musca domestica uicina MACQUART); Gasterophilidae, such as gastric botflies (Gasterophilus intestinalis); Hypodermatidae, such as the gadfly bullish (Hypodermabovis L.); Phoridae, such asMegaselia spircularis ; Culicidae, such as pale Culex (Culex pipiens pallens),Anopheles sinensis, tiger mosquito (Aedes albopictusandAedes japonicus; Pulicidae, such as cat flea (Ctenocephalides felis), dog flea (Ctenocephalides canis), human flea (Pulex irritans); Ixodidae such asIxodes ovatus Neumann; Lymantriidae such asEuproctis similes; Rhynchophoridae, such as rice weevil (Sitophilus zeamais); Vespidae such asVespa simillima xanthoptera Cameron; Blattellidae, such as red cockroaches (Blattela germanica); Blattidae, such as the American cockroach (Periplaneta americanaandPeriplaneta japonica; Pthiridae, such as lice (Phthirus pubis); Termitidae, such as the Japanese termite (Reticulitermes speratusand homemade termite (Coptotermes formosanus); and Ixodidae such asIxodes persulcatus; and Macronyssidae, such as tropical rat mites (Ornithonyssus bacoti).

Agents for agriculture, in particular insecticides or acaricides for agriculture containing substituted pyrazolecarboxylate derivative represented by the formula (I)or its salt of the present invention as an active ingredient, have a noticeable controlling effect on the above harmful insects, which are pests of agricultural crops in paddy fields, upland agricultural plants, fruit trees, plants, and other crops, flowers and ornamental plants, and the fact is such. For this reason, the desired impact of insecticides for agriculture of the present invention can be demonstrated by applying agents on rice fields, fields, fruit trees, plants, and other agricultural crops, seeds, flowers and ornamental plants, the water in the rice fields, the stalks and leaves or on the soil, at that time of year when it is expected occurrence of harmful insects, before or at the time when confirmed their appearance.

Plants, which can be used by the agent for agriculture of the present invention are not specifically limited and include, for example, plants, shown below.

Cereals (such as rice (Oryza sativa), barley (Hordeum vulgare), wheat (Triticum aestivuroL.), rye (Secale cereale), oats (Avena), maize (Zea mays L.), sorghum and the like); legumes (soybeans, beans radiant, horse beans, kidney beans, peanuts, etc.); fruit trees and fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherries, walnuts, almonds, banana, strawberries and the like); vegetables (cabbage, tomatoes, spinach, broccoli, lettuce, onion, onion, Welsh onion, green pepper, and the like); root crops (carrots, potatoes, potty, radish, Lotus root, turnips and the like); industrial crops (cotton, flax (Linum usitaissimum ), paper mulberry(Broussonetia kasinokiSIEB), edgeworthia momaganon (Edgeworthia papyrifera), rape (Brassica napus L.), beets (Beta vulgaris), hops, sugar cane (Saccharum officinarum), sugar beet (Beta vulgaris var.saccharifera), olives, rubber, coffee, tobacco, tea and the like); pumpkin (pumpkin, cucumber, watermelon, melon, etc.); grass garden grass, sorghum, Timothy grass, meadow clover, alfalfa, etc.); grass (zoysia Japanese, restavratsiya grass and the like); plants for herbs (lavender (Lavandula officinalisCHAIX), rosemary, thyme, parsley, pepper, ginger and the like); and flowers (chrysanthemums, roses, orchids and the like).

Recently began to develop genetically modified recombinant crops (plants resistant to herbicides, plants, resistant to harmful insects that have incorporated the gene generation insecticidal toxin resistant to the diseases of plants that have incorporated the gene producing the inductor's resistance to diseases, plants with improved taste, plants with improved properties canning, plants with improved yield, and the like), a technology using sex insect pheromones (chemicals that Deplete the pheromones leafrollers, cabbage moths, and the like), IPM (integrated pest control) using prirodnykh enemies of insects, and composition of the pesticide of the present invention can be used in combination or in the system together with such technologies.

Agent for agriculture of the present invention typically are prepared in easy to use forms, in accordance with the usual method of preparation agrochemicals.

That is, substituted pyrazolecarboxylate derivative represented by the formula (I)or salt of the present invention and, optionally, auxiliary substance is mixed with an appropriate use of the inert carrier in the appropriate proportions and prepared in the form of appropriate medication, such as a suspension, emulsifiable concentrate, soluble concentrate, wettable powder, dispersible in water, pellets, granules, fine powder, pill, packing or the like, by dissolution, dispersion, suspension, mixing, impregnation, adsorption or sticking.

The inert carrier used in the present invention may be either solid or liquid. As a material used as a solid carrier, can be cast soybean flour, cereal flour, wood flour, flour from the bark, saw dust, powdered tobacco stalks, powdered walnut shells of nuts, bran, powdered cellulose, is used, resin, such as powdered synthetic polymers and the like, clays (e.g. kaolin, bentonite and acid clay), only (e.g. talc and pyrophyllite), powders or flakes of silicon oxide (for example, diatomaceous earth, silica sand, mica and white carbon [synthetic highly dispersed silicic acid, also called finely dispersed hydrated silica or hydrated silicic acid, some of commercially available products contain calcium silicate as the main component]), inorganic or mineral powders, such as activated carbon, powdered sulfur, pumice, calcined diatomaceous earth, crushed brick, ash, sand, calcium carbonate, calcium phosphate and the like, plastic media, such as polyethylene, polypropylene, poly(vinylidenechloride) and the like, chemical fertilizers (e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and ammonium chloride) and compost. Such media can be used individually or as a mixture of two or more kinds of them.

The material used as the liquid media, which are selected from materials which are dissolved or that, even without such dissolution, capable of dispersing the active ingredient with adjuvant. Below is a specific clause shall emery a liquid medium, which can be used individually or as a mixture of two or more kinds of: 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 (for example, a simple ethyl ether, dioxane, cellosolve, simple DIPROPYLENE ether and tetrahydrofuran), aliphatic hydrocarbons (e.g. kerosene and mineral oil), aromatic hydrocarbons (e.g. benzene, toluene, xylene, solvent naphtha and alkylnaphthalene),halogenated hydrocarbons (e.g. dichloroethane, chloroform, carbon tetrachloride 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.

Below are specific examples of the adjuvant, which is used depending on the purpose or separately, or in combination of two or more species, or, in some cases, may not be used at all.

For emulsification, dispersion, dissolution and/or wetting compounds as the active ingredient is used surfactant. As surface-active substances may b the th provides a simple polyoxyethylenesorbitan esters, simple polyoxyethylenesorbitan esters, complex polyoxyethylene esters of higher fatty acids, polyoxyethylenated, polyoxyethylenesorbitan, polyoxyethylenesorbitan monooleate, alkylarylsulfonates, condensation products naphthalenesulfonic acids, ligninsulfonate and complex sulfate esters of higher alcohols.

In addition, to stabilize the dispersion of the compounds as the active ingredient, to make it sticky and/or link it can also be used adjuvants below, and it can be used adjuvants such as casein, gelatin, starch, methylcellulose, carboxymethylcellulose, Arabian gum, poly(vinyl alcohols), turpentine, oil of bran, bentonite and ligninsulfonate.

To improve the flowability of the solid product can be used the following adjuvants, namely, such as waxes, stearates, alkylphosphate and the like.

Adjuvants, such as condensation products naphthalenesulfonic acids and polycondensate phosphates, can be used as activator for plasticization dispersible products.

Adjuvants, such as silicone oil, can also be used as protivovspenivayushchie agent.

Adjuvants, such as 1,2-benzisothiazolin-3-one, p-chloro-m-Xylenol, butyl-p-hydroxybenzoate, also is there might be added as a preservative.

In addition, if necessary, can be added also functional distributing agents, amplifiers activity, such as a metabolic inhibitor of decomposition, such piperonylbutoxide, antifreeze agents, such as propylene glycol, antioxidants, such as BHT, ultraviolet absorbers and other additives.

The content of the compound as active ingredient may be changed if necessary, and the compound as active ingredient may be used in proportions selected appropriately in the range from 0.01 to 90 mass parts per 100 parts agents for agriculture. For example, fine powders or granules suitable for use the content of the compounds as the active ingredient is from 0.01 to 50 wt.%. In emulsifiable concentrate or wettable powders, it is from 0.01 to 50 wt.%.

Agent for agriculture of the present invention used to control a variety of insect pests in the following manner: it is used to crop, which is expected to appear harmful insects, or to such place, where the emergence and growth of harmful insects is undesirable, as such or after appropriate dilution with water or suspension in water or the like, to the number, effective for combating harmful insects.

The applied dosage of the agent for agriculture of the present invention varies depending on various factors such as the purpose, harmful insects, which have to fight the state of plant growth, the tendency to the appearance of harmful insects, weather, environmental conditions, the form of preparation, method of application, place of application and time of application. It can be selected appropriately in the range from 0.001 g to 10 kg, preferably from 0.01 g to 1 kg (in terms of the compounds as the active ingredient) per 10 Ares, depending on the purpose.

Agent for agriculture of the present invention can be used in a mixture with other insecticides, acaricides, nematicides, fungicides, biotic pesticides for agriculture or similar, to expand both spectrum of controllable kinds of harmful insects, and the period of time when effective application, or to reduce the dosage. In addition, insecticide for agriculture of the present invention can be used in combination with herbicides, plant growth regulators, fertilizers or the like, depending on the situations.

As other insecticides, acaricides and nematicides for agriculture, which used to indicated the Anna above objectives, can be given such insecticides, acaricides and nematicides for agriculture, 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, phoxim, isoxathion, pyraclofos, methidathion, chlorpyrifos, chlorpyrifos, predatation, diazinon, pirimiphosmethyl, fosalan, phosmet, dioxybenzone, finalpos, terbufos, ethoprophos, cadusafos, resolvents, spirodiclofen, metaflumizone, flubendiamide, DPS (NK-0795), fastcars, fenamiphos, solidagos, fosthiazate, isazofos, ethoprophos, fenthion, pastilan, dichlofenthion, thionazin, sulprofos, fensulfothion, diamides, pyrethrin, allethrin, prallethrin, resmethrin, permethrin, tefluthrin, bifenthrin, fenpropathrin, cypermethrin and α-cypermethrin, cigalotrin, λ - cigalotrin, deltamethrin, acrinathrin, fenvalerate, esfenvalerate, cicloprofen, etofenprox, halftracks, selflove, flucythrinate, fluvalinate, maternal, oxamyl, thiodicarb, aldicarb alankar, cartap, metolcarb, kelekar, propoxur, fenoxycarb, fenobucarb, ethiofencarb, fanatical, bifenazate, BPMC, carbaryl, Prentice, carbofuran, carbosulfan, the truck is icarb, benfuracarb, aldoxycarb, diafenthiuron, diflubenzuron, teflubenzuron, hexaflumuron, novaluron, lufenuron, flufenoxuron, chlorfluazuron, fenbutatin oxide, hydroxide tricyclohexyl, sodium oleate, potassium oleate, methoprene, hydroprene, binapacryl, amitraz, dicofol, kerzen, Chlorobenzilate, bromopropylate, tetradifon, bensultap, benoxinate, tebufenozide, methoxyfenozide, pyridalyl, chromafenozide, propargite, acehenese, endosulfan, giovanola, chlorfenapyr, fenpyroximate, tolpinrud, fipronil, tebufenpyrad, triazamate, etoxazole, hexythiazox, nicotine sulfate, nitenpyram, acetamiprid, thiacloprid, Imidacloprid, thiamethoxam, clothianidin dinotefuran, fluazinam, pyriproxifen, hydramethylnon, pyrimidifen, pyridaben, cyromazine, TPIC (tripropyl isocyanurate), pymetrozine, clofentezine, buprofezin, thiocyclam, fentahun, chinomethionat, indoxacarb, complexes polyctena, milbemectin, abamectin, emamectin-benzoate, spinosad, BT (Bacillus thuringiensis), azadirachtin, rotenone, hydroxypropyl starch, levamisole hydrochloride, METAM-sodium, morantel titrat, dazomet, trihemic, pasteuria penetrans, Monacrosporium-phymatophagum and the like.

As fungicides for agriculture, used for the same purpose, as indicated above, may be provided such fungicides for agriculture as sulfur, lime sulfur, cos the main copper sulfate, iprobenfos, edifenphos, tolclofos-methyl, thiram, polycarbamate, zineb, MANEB, MANCOZEB, propineb, tiopinac, thiophenemethyl, benomyl, iminoctadine acetate, iminoctadine albella, mepronil, flutolanil, pencycuron, parameter, tifusari, metalaxyl, oxadixyl, napropamide, dichlofluanid, glucolipid, CHLOROTHALONIL, kresoxim-methyl, phenoxyl, hymexazol, etridiazole, perimed, procymidon, vinclozolin, iprodione, triadimefon, bitertanol, triflumizole, econazole, fluconazole, propiconazol, difenoconazol, myclobutanil, tetraconazole, hexaconazole, tebuconazole, tadini, kabekona, prochloraz, peyratout, tsyprokonazolu, isoprothiolane, fenarimol, Pyrimethanil, marripalem, pirivenas, fluazinam, triforine, declomycin, AZOXYSTROBIN, thiadiazin, Captan, provenzal, acibenzolar-S-methyl, phtalic, tricyclazole, pyroxylin, chinomethionat, oxolinic acid, dithianon, kasugamycin, validamycin, polyoxin, blasticidin, streptomycin and the like.

Similarly, as herbicides, can be brought herbicides such as glyphosate, sulfosate, glufosinate, bialaphos, butamifos, asbroker, promecarb, benthiocarb, perimutter, Azul, linuron, damron, Sauron, encultured methyl, cycloaliphatic, chinaculture, pyrazosulfuron ethyl azimsulfuron, imazosulfuron, tanishlar, alachlor, pretilachlor, clomipram, this is benzene, 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, hislopi-ethyl, bentazon, calcium peroxide, and the like.

Regarding biotic pesticides, the same effect as above can be expected when using the agent for agriculture of the present invention in a mixture with, for example, viral drugs prepared from nuclear polyhedrosis virus (NPV), virus granulata (GV), virus cytoplasmic polyhedrosis (CPV), virus entomopox (investment) and the like; microbial pesticides that are used as insecticides or nematicides, such asMonacrosporium phymatophagum,Steinernema carpocapsae,Steirxernema kushidai,Pasteuria penetransand the like; microbial pesticides that are used as fungicides, such asTrichodermalignorum,Agrobacterium radiobactor, non-pathogenicErwinia carotovora,Bacillus subtilisand the like; and biotic pesticides that are used as herbicides, such asXanthomonascampestrisand the like.

In addition, the agent for agriculture this izaberete the Oia can be used in combination with biotic pesticides, including natural enemies, such as wasps are parasites (Encarsia formosa), wasps, parasites (Aphidius colemani), haloorange insects (Aphidoletes aphidimyza), wasps, parasites (Diglyphus isaea), ticks-parasites (Dacnusa sibirica), predatory mites (Phytoseiuluspersimilis), predatory mites (Amblyseiuscucumeris), predatory bugs (Orius sauteriand the like; microbial pesticides, such asBeauveria brongniartii,and the like; and pheromones, such as (Z)-10-tetradecanoate, (E,Z)-4,10-tetradecanoate, (Z)-8-dodecalactam, (Z)-11-tetradecanoate, (Z)-13-ECOSAN-10-he like.

Examples

Substituted pyrazolecarboxylate derivative represented by the formula (I), and substituted aniline derivative represented by the formula (II), and substituted pyrazolylborate acid represented by the formula (IV), which are intermediate compounds of the present invention, is described hereinafter with reference to examples, which should not be construed as limiting.

Example 1

Obtain 1,3-dimethyl-5-cryptomaterial-4-carboxylic acid (compound No. 4-1)

4-Iodine-1,3-dimethyl-5-cryptomaterial (8.7 g, 30 mmol) dissolved in tetrahydrofuran (87 ml) and slowly add a solution (1.6 m, 28 ml) n-utility in hexane in an argon atmosphere while cooling the mixture of dry ice/acetone (not higher than -60°C). After stirring at -0°C for 30 min the mixture was gradually warmed to room temperature, equalising it with carbon dioxide. The reaction mixture was poured into water, the organic layer removed and the aqueous layer was acidified with hydrochloric acid. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and concentrate under reduced pressure. The obtained crude crystal was washed with hexane, to give the desired compound (4,67 g) in the form of crystals.

Yield 74%.

Property: melting point 124-125,5°C.

Example 2

Obtain N-{3-isobutyl-4-[1-methoxy-2,2,2-Cryptor-1-(trifluoromethyl)ethyl]phenyl}-1,5-dimethyl-3-cryptomaterial-4-carboxamide (compound No. 1-211)

1,5-Dimethyl-3-cryptomaterial-4-carboxylic acid (2,09 g, 10 mmol) is dissolved in thionyl chloride and the mixture is heated to boiling under reflux for 3 hours. The mixture is concentrated under reduced pressure to obtain 1,5-dimethyl-3-cryptomaterial-4-carbonylchloride. The resulting carbonylchloride added to a solution of 3-isobutyl-4-[1-methoxy-2,2,2-Cryptor-1-(trifluoromethyl)ethyl]aniline (3,29 g, 10 mmol) and triethylamine (3.03 g, 30 mmol) in tetrahydrofuran (30 ml) and the mixture heated to boiling under reflux for 2 hours. The reaction mixture was diluted with ethyl acetate, washed with water and dried over magnesium sulfate. After concentration under reduced pressure obtained is the residue purified column chromatography on silica gel (hexane:ethyl acetate=1:1), to give the desired compounds (of 3.64 g) in the form of crystals.

Yield 70%.

Property: melting point 138-139°C.

Example 3

Obtaining N-methoxymethyl-N-{3-isobutyl-4-[1-Patxi-2,2,2-Cryptor-1-(trifluoromethyl)ethyl]phenyl}-1,5-dimethyl-3-cryptomaterial-4-carboxamide (compound No. 1-222)

Sodium hydride (32 mg, 60%, 0.8 mmol) suspended in tetrahydrofuran (10 ml) and add dropwise a solution of N-{3-isobutyl-4-[1-methoxy-2,2,2-Cryptor-1-(trifluoromethyl)ethyl]phenyl}-1,5-dimethyl-3-cryptomaterial-4-carboxamide (250 mg, 0.48 mmol) in tetrahydrofuran (5 ml). After stirring at room temperature for 30 min add the solution is simple chloromethylmethylether ester (64 mg, 0.8 mmol) in tetrahydrofuran (2 ml) and the mixture is stirred for 5 hours. The reaction mixture is poured into dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, concentrated under reduced pressure and the resulting residue is purified column chromatography on silica gel (hexane:ethyl acetate=2:1) to give the desired compound (238 mg).

Yield: 88%.

Property: nD1,4669 (22,4°C).

Example 4

Obtaining 2-methyl-5-n-propyl-4-[1,2,2,2-titrator-1-(trifluoromethyl)ethyl]aniline (compound No. 3-1)

5-n-Propyl-2-methylaniline (14.9 g, 0.1 mol) was diluted with a mixed process is ielem (300 ml) simple tert-butyl methyl ether-water (1:1) and sequentially add heptafluoroisopropyl (29,6 g, 0.1 mol), tetrabutylammonium hydrosulfate (3.4 g, 0.01 mol), sodium bicarbonate (of 8.4 g, 0.1 mol) and dithionite sodium (17 g, 0.1 mol). The mixture is stirred over night at room temperature. The reaction mixture was diluted with hexane, washed twice 3 n hydrochloric acid and washed with aqueous sodium bicarbonate solution and saturated salt solution. The organic layer is dried over magnesium sulfate and concentrate under reduced pressure. The residue is purified by chromatography on silica gel (hexane:ethyl acetate=5:1) to give the desired compound (28.5 g).

Yield: 90%.

Property:1H-NMR [CDCl3/TMS, the value δ (ppm)] to 7.09 (s, 1H), is 6.54 (s, 1H), 3,76 (users, 2H), 2.63 in (m, 2H), 2.13 in (m, 3H), 1,58 (m, 2H), of 0.96 (t, 3H).

Example 5

Getting 4-[1-methoxy-2,2,2-Cryptor-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylaniline (compound No. 3-3)

2-Methyl-5-n-propyl-4-[1,2,2,2-titrator-1-(trifluoromethyl)ethyl]aniline (1.6 g, 5 mmol) dissolved in 28% solution (9.6 g) of sodium methoxide in methanol and the mixture is heated to boiling under reflux for 3 hours. After she was given the opportunity to cool, the reaction mixture is poured into ice water and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and concentrate under reduced pressure. The resulting residue is purified column chromatography on silica gel (hexane:ethyl shall zitat=5:1) to give the desired compound (1.31 g).

Yield: 79%.

Property:1H-NMR [CDCl3/TMS, the value δ (ppm)] 7,10 (s, 1H), 6,66 (s, 1H), 3.72 points users, 2H), 3,42 (s, 3H), 2,84 (m, 2H), and 2.14 (s, 3H), of 1.61 (m, 2H), and 1.00 (t, 3H).

Example 6

Obtaining 2-methyl-5-n-propyl-4-[2,2,2-Cryptor-1-(trifluoromethyl)ethyl]aniline (compound No. 3-2)

2-Methyl-5-n-propyl-4-[1,2,2,2-titrator-1-(trifluoromethyl)ethyl]aniline (1.6 g, 5 mmol) dissolved in dimethyl sulfoxide (20 ml), add small portions of borohydride sodium (378 mg, 10 mmol) and the mixture was stirred at 60°C for 5 hours. Add ice in small portions to the reaction mixture and then add acetic acid dropwise. The reaction mixture was diluted with ethyl acetate, the organic layer is washed 4 times with water, dried over magnesium sulfate and concentrated under reduced pressure to give the desired compound (1.47 g).

Yield: 99%.

Property:1H-NMR [CDCl3/TMS, the value δ (ppm)] to 7.18 (s, 1H), is 6.54 (s, 1H), 4,45-4,20 (user., 2H), 4,27 (m, 1H), 2,50 (DD, 2H), and 2.14 (s, 3H), of 1.57 (m, 2H), and 0.98 (t, 3H).

Example 7

Obtain N-{4-[1-methoxy-2,2,2-Cryptor-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylphenyl}-1,3,5-trimethylpyrazole-4-carboxamide (compound No. 2-15)

1,3,5-Trimethylpyrazole-4-carbonylchloride (172 mg, 1 mmol), 4-[1-methoxy-2,2,2-Cryptor-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylaniline (329 mg, 1 mmol) and triethylamine (303 mg, 3 mmol) dissolved in tetrahydrofuran (10 ml) and the mixture is heated at the boiling OBR is Tim refrigerator for 3 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer is dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue is purified column chromatography on silica gel (hexane:ethyl acetate=1:2), to give the desired compound (360 mg).

Yield: 77%.

Property: melting point 132-134°C.

Example 8

Obtaining N-acetyl-N-{4-[1-methoxy-2,2,2-Cryptor-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylphenyl}-1,3,5-trimethylpyrazole-4-carboxamide (compound No. 2-16)

Sodium hydride (32 mg, 60%, 0.8 mmol) suspended in tetrahydrofuran (10 ml) and add dropwise a solution of N-{4-[1-methoxy-2,2,2-Cryptor-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylphenyl}-1,3,5-trimethylpyrazole-4-carboxamide (250 mg, of 0.53 mmol) in tetrahydrofuran (5 ml). After stirring at room temperature for 30 minutes, add a solution of acetic anhydride (80 mg, 0.78 mmol) in tetrahydrofuran (2 ml) and the mixture is stirred for one day. The reaction mixture is poured into dilute hydrochloric acid and the mixture extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, concentrated under reduced pressure and the resulting residue is purified column chromatography on silica gel (hexane:ethyl acetate=1:3) to give the desired compound (139 mg).

Yield: 52%.

With aisto: n D1,4905 (25,9°C).

Example 9

Obtain N-{2-methyl-5-n-propyl-4-[2,2,2-Cryptor-1-(trifluoromethyl)ethyl]phenyl-2-methyl-5-n-propylphenyl}-1,3,5-trimethylpyrazole-4-carboxamide (compound No. 2-13)

According to the method of example 7, except that 2-methyl-5-n-propyl-4-[2,2,2-Cryptor-1-(trifluoromethyl)ethyl]aniline is used instead of 4-[1-methoxy-2,2,2-Cryptor-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylaniline, the reaction is carried out for 3 hours to give the desired compound.

Yield: 66%.

Property: melting point 128-131°C.

Example 10

Obtain N-{3-isobutyl-4-[1-methoxy-2,2,2-Cryptor-1-(trifluoromethyl)ethyl]phenyl}-1,3,5-trimethylpyrazole-4-carboxamide (compound No. 1-155)

1,3,5-trimethylpyrazole-4-carbonylchloride (3,93 g of 22.8 mmol), 3-isobutyl-4-[1-methoxy-2,2,2-Cryptor-1-(trifluoromethyl)ethyl]aniline (5.0 g, of 15.2 mmol) and triethylamine (of 3.07 g, 30.4 mmol) was dissolved in tetrahydrofuran (100 ml) and the mixture heated to boiling under reflux for 5 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer is dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained crude crystal was washed with simple ether to give the desired compound (5,62 g).

Yield: 80%.

Property: melting point 189-190°C.

Example 11

Obtaining N-ethoxymethyl-N-{3-isobutyl-4[1-methoxy-2,2,2-Cryptor-1-(trifluoromethyl)ethyl]phenyl}-1,3,5-trimethylpyrazole-4-carboxamide (compound No. 1-145)

Sodium hydride (29 mg, 60%, 0.73 mmol) suspended in tetrahydrofuran (10 ml) and add dropwise a solution of N-{3-isobutyl-4-[1-methoxy-2,2,2-Cryptor-1-(trifluoromethyl)ethyl]phenyl}-1,3,5-trimethylpyrazole-4-carboxamide (260 mg, 0.48 mmol) in tetrahydrofuran (5 ml). After stirring at room temperature for 30 min add the solution is simple chloromethylation ester (70 mg, 0.73 mmol) in tetrahydrofuran (2 ml) and the mixture is stirred for one day. The reaction mixture is poured into dilute hydrochloric acid and the mixture extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, concentrated under reduced pressure and the resulting residue is purified column chromatography on silica gel (hexane:ethyl acetate=1:3) to give the desired compound (200 mg).

Yield: 69%.

Property: nD1,4892 (22,4°C).

Example 12

Obtaining N-isobutylketone-N-{3-isobutyl-4-[1-methoxy-2,2,2-Cryptor-1-(trifluoromethyl)ethyl]phenyl}-1,3,5-trimethylpyrazole-4-carboxamide (compound No. 1-152)

Sodium hydride (29 mg, 60%, 0.73 mmol) suspended in tetrahydrofuran (10 ml) and add dropwise a solution of N-{3-isobutyl-4-[1-methoxy-2,2,2-Cryptor-1-(trifluoromethyl)ethyl]phenyl}-1,3,5-trimethylpyrazole-4-carboxamide (260 mg, 0.48 mmol) in tetrahydrofuran (5 ml). After stirring at room temperature for 30 min dobavlaut solution isobutylparaben (100 mg, 0.73 mmol) in tetrahydrofuran (2 ml) and the mixture is stirred for one day. The reaction mixture is poured into dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, concentrated under reduced pressure and the resulting residue is purified column chromatography on silica gel (hexane:ethyl acetate=1:1) to give the desired compound (280 mg).

Yield: 91%.

Property: nD1,4829 (22,3°C).

Example 13

Obtain N-{3-isobutyl-4-[2,2,2-Cryptor-1-(trifluoromethyl)ethyl]phenyl}-1,3,5-trimethylpyrazole-4-carboxamide (compound No. 1-123)

1,3,5-Trimethylpyrazole-4-carbonylchloride (of 2.09 g, 10.0 mmol), 3-isobutyl-4-[2,2,2-Cryptor-1-(trifluoromethyl)ethyl]aniline (2.0 g, 6,69 mmol) and triethylamine (1.35 g, a 13.4 mmol) dissolved in tetrahydrofuran (60 ml) and the mixture heated to boiling under reflux for 5 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer is dried over anhydrous magnesium sulfate, concentrated under reduced pressure and the resulting residue is purified column chromatography on silica gel (hexane:ethyl acetate=1:3) to give the desired compound (2,41 g).

Yield: 77%.

Property: melting point 148-151°C.

Example 14

Obtaining N-acetyl-N-{3-isobutyl-4-[2,2,2-Cryptor-1-(trifluoromethyl)ethyl]phenyl}-1,3,trimethylpyrazole-4-carboxamide (compound No. 1-125)

Sodium hydride (38 mg, 60%, 0.96 mmol) suspended in tetrahydrofuran (10 ml) and add dropwise a solution of N-{3-isobutyl-4-[2,2,2-Cryptor-1-(trifluoromethyl)ethyl]phenyl}-1,3,5-trimethylpyrazole-4-carboxamide (300 mg, 0.64 mmol) in tetrahydrofuran (5 ml). After stirring at room temperature for 30 min add a solution of acetylchloride (75 mg, 0.96 mmol) in tetrahydrofuran (2 ml) and the mixture is stirred for one day. The reaction mixture is poured into dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, concentrated under reduced pressure and the resulting residue is purified column chromatography on silica gel (hexane:ethyl acetate=1:3) to give the desired compound (90 mg).

Yield: 28%.

Property: nD1,5021 (22,5°C).

Comparative example obtain 1

4-iodine-1,3-dimethyl-5-cryptomaterial

Iodine (30 g) dissolved in 60% sulfuric acid (fuming, 80 g) and slowly added 1,3-dimethyl-5-cryptomaterial (13,12 g, 80 mmol) under cooling on ice. The mixture is stirred at 0°C for 2 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with aqueous sodium thiosulfate and saturated salt solution, dried over magnesium sulfate and concentrate under reduced pressure. Obtained the crude crystal was washed with hexane to give the desired compound (20 g) in the form of crystals.

Yield 86%.

Property:1H-NMR [CDCl3/TMS, the value δ (ppm)] 3,98 (s, 3H), and 2.26 (s, 3H).

Specific examples of the preparation and the sample of the study the present invention are described below, but they should not be construed as limiting the scope of the present invention.

As used in the examples, the terms "part" and "parts" are parts by weight.

Sample preparation 1

Each compound listed in table 1
or table 2
10 h
Xylene70 h
N-organic10 h
A mixture of simple polyoxyethyleneglycol ether and
the Las calcium
10 h

Emulsifiable concentrate prepared by homogeneous mixing of the above ingredients to dissolve.

Example preparation of 2

Each compound listed in table 1
or table 2
3 hours
The clay powder82 h
Powder diatomaceous earth 15 h

The fine powder prepared by homogeneous mixing and grinding of the above ingredients.

Example preparation of 3

Each compound listed in table 1
or table 2
5 h
Mixed powder of bentonite clay90 h
Calcium ligninsulfonate5 h

Granules prepared by homogeneous mixing of the above ingredients and kneading the resulting mixture together with an appropriate amount of water, followed by granulation and drying.

Example preparation of 4

Each compound listed in table 1
or table 2
20 h
A mixture of kaolin and synthetic highly dispersed silicic acid75 h
A mixture of simple nonylphenylether ether of polyoxyethylene and Las calcium5 pieces

Wettable powder is prepared by homogeneous mixing and grinding the above ing is eventov.

Example study 1:

Acaricidal effect on clasic spider bimaculated (Tetranychus urticae)

The disk sheet kidney beans 2 cm in diameter is placed on moist filter paper. Ten adult males of klasika spider bimaculated inoculant on each disk sheet and pollinate 50 ml of the investigated solution obtained by diluting a preparation containing each of the compounds listed in table 1 or table 2, as an active ingredient, to establish each of the concentrations at 500 hours/million, 50 hours/million and 5 hours/million two days after treatment, consider surviving mites. Adjusted mortality is calculated using the following equation, and acaricidal activity is evaluated according to the criteria shown below. The experiment is carried out twice under the conditions, at 25°C.

Corrected mortality (%)=The number of surviving mites in the untreated group-The number of surviving mites in the treated group× 100
The number of surviving mites in the untreated group

Criteria:

A -- Adjusted mortality 100%

B --- Adjusted mortality 99-90%

C --- Adjusted mortality 89-80%

D --- Adjusted mortality 79-50%

As comparative compounds used compound No. 1-163 and 1-164 described in the patent application of Japan JP-A-2003-48878.

In the above studies of compounds No. 1-1, 1-3, 1-4, 1-6, 1-8, 1-10, 1-12, 1-13, 1-15, 1-16, (1-25)-(1-28), 1-31, (1-34)-(1-37), 1-45, (1-47)-(1-49), (1-51)-(1-54), 1-56, 1-57, 1-59, 1-67, (1-69)-(1-72), (1-74)-(1-76), 1-89, (1-101)-(1-114), (1-120)-(1-160), (1-176)-(1-225), 1-228, 1-234, 1-246, 1-258, 1-260, 1-266, 1-270, 1-282, 1-285, 1-294, (1-306)-(1-325), (1-327)-(1-332), (1-335)-(1-337), (1-339)-(1-342), (1-344)-(1-358), (1-361)-(1-373), (1-375)-(1-380), (1-382)-(1-384), (1-386)-(1-389), (1-391)-(1-394), 1-396, (1-399)-(1-406), (1-412)-(1-416), (1-420)-(1-423), (1-425)-(1-427), (1-429)-(1-433), (1-435)-(1-439), (1-441)-(1-445), 1-448, (1-450)-(1-452), (1-454)-(1-463), (1-467)-(1-470), 1-473, 1-477, 1-478, (1-482)-(1-487), (1-489)-(1-493), (1-496)-(1-502), 1-510, 1-514, 1-515, 1-518, 1-519, (1-523)-(1-527), 1-531, (1-539)-(1-541), (1-546)-(1-549), 2-13, (2-15)-(2-17), (2-21)to(2-23), 2-25, 2-34, (2-36)-(2-39), (2-41)-(2-43 and 2-45 of the present invention show activity A at any concentration, 500 hours/million, 50 hours/million and 5 hours/million, and compound No. 1-23, 1-32, 1-78, 1-173, 1-284, 1-326, 1-334, 1-338, 1-343, 1-385, (1-397)-(1-398), 1-408, 1-410, 1-417, 1-440, 1-447, 1-449, 1-464, 1-472, 1-475, 1-476, 1-479, 1-480, (1-504)-(1-506), 1-509, 1-521, 1-529, 1-530, 1-533, 1-542, (2-26)to(2-33), 2-40 and 2-46 show activity A at any concentration, 500 hours/million and 50 hours/million In contrast, both control connections are not shown acaricidal activity even at a concentration of 500 PM/million

In accordance with the present invention, can be obtained agents for agriculture, in particular, insecticides and acaricides, possessing superior properties compared to conventional technologies.

This application is based on patent applications No. 234405/2005, 322531/2005 and 114937/2006 filed in Japan, the contents of which are incorporated in this description by reference.

Although the present invention is shown and described with reference to its preferred embodiments of specialists in this field will be clear that there can be produced various changes in form and details without deviating from the scope of the present invention covered by the appended claims.

All patents, patent publications and other publications identified or described in this description are incorporated by reference in their entirety.

1. Substituted pyrazolecarboxylate derivative represented by the formula (I):

where R11A is a) a hydrogen atom, 2A)1-C8alkyl group. 3A) Halogens1-C6alkyl group, 4A) C1-C6alkylcarboxylic group 5A) Halogens1-C6alkylcarboxylic group 6A)2-C6alkenylboronic group 13A) C2-C6alkenylphenol group, 17A)1-C10alkoxyl1-C61-C6alkoxyl1-C6alkyl group, 19a)2-C6alkenylacyl1-C6alkyl group, 20A) C1-C6alkoxyl1-Cbalkoxy, C1-C6alkyl group, 29A) panels1-C6alkoxyl1-C6alkyl group, 31A)1-C16alkoxycarbonyl group, 32A)1-C6alkoxyl1-C6alkoxycarbonyl group, 33a) Halogens1-C6alkoxycarbonyl group, 34a)2-C6altneratively group, 35A) C1-C6alkylthiomethyl group, 42A) panels1-C6alkyl group, 43A) substituted phenyls1-C6alkyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (C) nitro and (d) C1-C6alkyl group, 44a) phenylcarbonylamino group, 45A) substituted phenylcarbonylamino group having on the ring one or more identical or different substituents selected from a) halogen atom, (C) nitro group, (d) C1-C6alkyl group, (e) Halogens1-C6alkyl groups and (f) C1-C6alkoxygroup 47A) substituted geterotsiklicheskikh group selected from pyrazinecarboxamide group, pyrazolecarboxylate group, thiophencarboxylic g is uppy and diazocarbonyl group, having on the ring one or more identical or different substituents selected from (d) C1-C6alkyl group, 48A) phenoxycarbonyl group, 50A) venoxis1-C6alkylcarboxylic group, 53A) substituted phenylsulfonyl group having on the ring one or more identical or different substituents selected from a) halogen atom, 58A) dis1-C6alkylammonium, where the alkyl groups are the same or different, 59A)3-C6cycloalkylcarbonyl group, 61A) C1-C6alkyls3-C6cycloalkylcarbonyl group, 63A) panels1-C6alkylcarboxylic group, 65A) panels3-C6cycloalkylcarbonyl group, 68A)1-C6alkoxyl1-C6alkylcarboxylic group, 72A)1-C6alkylcarboxylic1-C6alkyl group, 73a) C1-C6alkylcarboxylic1-C6alkylcarboxylic group or a)1-C6alkoxycarbonyl1-C6alkylcarboxylic group;
R21b is a) a hydrogen atom, 2b), a halogen atom or 7b) C1-C6alkoxygroup;
G represents 1)2-C10alkyl group, 3C)3-C10alkenylphenol group, or 11)3-C8cycloalkyl1-C6alkyl group;
represents an oxygen atom;
X may be the same or different and represent Id) a hydrogen atom, 2d) halogen atom or 5d) C1-C6alkyl group;
Y1represents 2E) C1-C6alkyl group, 3E) Halogens1-C6alkyl group or 4E)2-C6alkenylphenol group;
Y2may be the same or different and represent 2f) halogen atom,
9f) C1-C6alkyl group, 10f) Halogens1-C6alkyl group or 31f) C1-C6allylthiourea;
m is 1 or 2; and
n is 1,
or its salt.

2. Substituted pyrazolecarboxylate derivative according to claim 1, where R11A is a) a hydrogen atom, 2A)1-C8alkyl group, 3A) Halogens1-C6alkyl group, 4A) C1-C6alkylcarboxylic group 5A) Halogens1-C6alkylcarboxylic group 6A)2-C6alkenylboronic group 13A)2-C6alkenylphenol group, 17A)1-C10alkoxyl1-C6alkyl group, 18a) Halogens1-C6alkoxyl1-C6alkyl group, 19a)2-C6alkenylacyl1-C6alkyl group, 20A)1-C6alkoxyl1-C6alkoxy, C1-C6alkyl group, 29A) panels1-C6alkoxyl1-C6alkalinuria, 31A)1-C16alkoxycarbonyl group, 32A)1-C6alkoxyl1-C6alkoxycarbonyl group, 33a) Halogens1-C6alkoxycarbonyl group, 34a)2-C6altneratively group, 35A) C1-C6alkylthiomethyl group, 42A) panels1-C6alkyl group, 43A) substituted phenyls1-C6alkyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (C) nitro and (d) C1-C6alkyl group, 44a) phenylcarbonylamino group, 45A) substituted phenylcarbonylamino group having on the ring one or more identical or different substituents selected from a) halogen atom, (C) nitro group, (d) C1-C6alkyl group, (e) Halogens1-C6alkyl groups and (f) C1-C6alkoxygroup 47A) substituted geterotsiklicheskikh group selected from pyrazinecarboxamide group, pyrazolecarboxylate group, thiophencarboxylic group and diazocarbonyl group having on the ring one or more identical or different substituents selected from (d) C1-C6alkyl group, 48A) phenoxycarbonyl group, 50A) venoxis1-C6alkylcarboxylic group, 53A) substituted phenylsulfonyl group, with n the ring one or more identical or different substituents, selected from a) halogen atom, 58A) dis1-C6alkylammonium, where the alkyl groups are the same or different, 59A)3-C6cycloalkylcarbonyl group, 61 (a) C1-C6alkyls3-C6cycloalkylcarbonyl group, 63A) panels1-C6alkylcarboxylic group, 65A) panels3-C6cycloalkylcarbonyl group, 68A) C1-C6alkoxyl1-C6alkylcarboxylic group, 73a)1-C6alkylcarboxylic1-C6alkylcarboxylic group or a)1-C6alkoxycarbonyl1-C6alkylcarboxylic group, or its salt.

3. Substituted pyrazolecarboxylate derivative according to claim 1 or 2, where R21b is a) a hydrogen atom, 2b), a halogen atom or 7b) C1-C6alkoxygroup.

4. Substituted pyrazolecarboxylate derivative according to claim 1 or 2, where G is a 1 C)2-C10alkyl group, 3C)3-C10alkenylphenol group, or 11)3-C8cycloalkyl1-C6alkyl group, or its salt.

5. Substituted pyrazolecarboxylate derivative according to claim 1 or 2, where X is a 1d) a hydrogen atom, 2d) halogen atom or 5d) C1-C6alkyl group, or its salt.

6. Substituted pyrazolecarboxylate derivative according to claim 1 or 2, where Z is predstavljaet an oxygen atom;
Y1represents 2E) C1-C6alkyl group, 3E) Halogens1-C6alkyl group or 4E)2-C6alkenylphenol group;
Y2may be the same or different and represent 2f) halogen atom,
9f) C1-C6alkyl group, 10f) Halogens1-C6alkyl group or 31f) C1-C6allylthiourea, or its salt.

7. Substituted pyrazolecarboxylate derivative according to claim 1, where R11A is a) a hydrogen atom, 4A) C1-C6alkylcarboxylic group 5A) Halogens1-C6alkylcarboxylic group, 17A)1-C10alkoxyl1-C6alkyl group, 18a) Halogens1-C6alkoxyl1-C6alkyl group, 31A)1-C16alkoxycarbonyl group, 33a) Halogens1-C6alkoxycarbonyl group or 68A)1-C6alkoxyl1-C6alkylcarboxylic group;
R21b is a) a hydrogen atom or 7b) C1-C6alkoxygroup;
G represents 1C)2-C10alkyl group;
Z represents an oxygen atom;
X represents 1d) a hydrogen atom;
Y1represents 2E) C1-C6alkyl group;
Y2can be odinakovimi or different and represent 2f) atom Galaga is a,
9f) C1-C6alkyl group or 10f) Halogens1-C6alkyl group, or its salt.

8. Acaricide for agriculture containing substituted pyrazolecarboxylate derivative according to claims 1 to 7 or its salt as an active ingredient.

9. How to apply acaricide for agriculture, which includes the processing target plants or soil an effective amount of acaricide for agriculture in item 8 for combating harmful organisms in useful plants.

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

R11A is a) a hydrogen atom, 2A)1-C8alkyl group, 3A) Halogens1-C6alkyl group, 4A)1-C6alkylcarboxylic group 5A) Halogens1-C6alkylcarboxylic group 6A)2-C6alkenylboronic group 13A)2-C6alkenylphenol group, 17A)1-C10alkoxyl1-C6alkyl group, 18a) Halogens1-C6alkoxyl1-C6alkyl group, 19a)2-C6alkenylacyl1-C6alkyl group, 20A) C1-C6alkoxyl1-C6alkoxy, C1-C6alkyl group, 29A) panels1-C6alkoxyl1-C6alkyl group, 31A)1-C1 alkoxycarbonyl group, 32A)1-C6alkoxyl1-C6alkoxycarbonyl group, 33a) Halogens1-C6alkoxycarbonyl group, 34a)2-C6altneratively group, 35A) C1-C6alkylthiomethyl group, 42A) panels1-C6alkyl group, 43A) substituted phenyls1-C6alkyl group having on the ring one or more identical or different substituents selected from a) halogen atom, (C) nitro and (d) C1-C6alkyl group, 44a) phenylcarbonylamino group, 45 (a) substituted phenylcarbonylamino group having on the ring one or more identical or different substituents selected from a) halogen atom, (C) nitro group, (d) C1-C6alkyl group, (e) Halogens1-C6alkyl groups and (f) C1-C6alkoxygroup 47A) substituted geterotsiklicheskikh group selected from pyrazinecarboxamide group, pyrazolecarboxylate group, thiophencarboxylic group and diazocarbonyl group having on the ring one or more identical or different substituents selected from (d) C1-C6alkyl group, 48A) phenoxycarbonyl group, 50A) venoxis1-C6alkylcarboxylic group, 53A) substituted phenylsulfonyl group having on the ring one or more of the LCO identical or different substituents, selected from a) halogen atom, 58A) dis1-C6alkylammonium, where the alkyl groups are the same or different, 59A)3-C6cycloalkylcarbonyl group, 61A) C1-C6alkyls3-C6cycloalkylcarbonyl group, 63A) panels1-C6alkylcarboxylic group, 65A) panels3-C6cycloalkylcarbonyl group, 68A)1-C6alkoxyl1-C6alkylcarboxylic group, 72A)1-C6alkylcarboxylic1-C6alkyl group, 73a) C1-C6alkylcarboxylic1-C6alkylcarboxylic group or a)1-C6alkoxycarbonyl1-C6alkylcarboxylic group;
R21b is a) a hydrogen atom, 2b), a halogen atom or 7b) C1-C6alkoxygroup;
G represents 1C)2-C10alkyl group, 3C)3-C10alkenylphenol group or 11S)3-C8cycloalkylcarbonyl group;
X may be the same or different and represent 1d) a hydrogen atom, 2d) halogen atom or 5d) C1-C6alkyl group;
n is 1,
or its salt.

11. Substituted aniline derivative of claim 10, where R11A is a) a hydrogen atom, 2A) C1-C6alkyl group, 3A) Halogens1-C6alkyl group, 4A) 1-C6alkylcarboxylic group 5A) Halogens1-C6alkylcarboxylic group, 17A) C1-C6alkoxyl1-C6alkyl group, 18a) Halogens1-C6alkoxyl1-C6alkyl group, 31A)1-C16alkoxycarbonyl group, 33a) Halogens1-C6alkoxycarbonyl group, 44a) phenylcarbonylamino group or 45A) substituted phenylcarbonylamino group having on the ring one or more identical or different substituents selected from a) halogen atom, (b) ceanography, (C) nitro group, (d) C1-C6alkyl group, (e) Halogens1-C6alkyl groups and (f) C1-C6alkoxygroup;
R21b is a) a hydrogen atom, 2b), a halogen atom or 7b) C1-C6alkoxygroup;
G represents 1C)2-C10alkyl group; and
X represents 1d) a hydrogen atom or 5d) C1-C6alkyl group, or its salt.

12. 1,3-Dimethyl-5-cryptomaterial-4-carboxylic acid or its salt.



 

Same patents:

FIELD: chemistry.

SUBSTANCE: invention relates to novel malononitryl derivatives of formula (I), which can be applied to fight pest insects. In formula (I) R1 represents hydrogen atom; R2 represents hydrogen atom; R represents hydrogen atom; R4 represents C1-C5-alkyl group substituted with at least one halogen atom, C2-C5-alkenyl group; R5 represents hydrogen atom, halogen atom, C1-C5-alkyl group; at least one of X1, X2 and X3 values represents CR6, the other represent nitrogen atoms; R represents hydrogen atom, halogen atom, cyanogroup, nitrogroup, formyl group, C1-C5-alkyl group optionally substituted with at least one halogen atom, C1-C5-alkyltiogroup, substituted with at least one halogen atom, C2-C6-alkylcarbonyl group substituted with at east one halogen atom, C2-C5-alkoxycarbonyl group or group (CH2)mQ, where m = 0, and Q stands for phenyl; and in case when one of R5 and R6 is bonded with two atoms in adjacent positions or two R6 are bonded with two atoms in adjacent positions, they can be bonded to each other in end positions with formation of C2-C6-alkandiyl group, or C4-C6-alkenediyl group. Invention also relates to composition and method used to fight pest-insects.

EFFECT: obtaining novel malononitryl derivatives of formula (I), which can be applied to fight pest-insects.

11 cl, 90 ex

FIELD: chemistry.

SUBSTANCE: invention relates to new compounds with general formula (I) , where R1 and R2 are independently chosen from hydrogen, halogen, nitro, alkyl, alkylaryl and XYR5; X and Y are independently chosen from O and (CR6R7)n; R3 represents hydrogen, alkyl or M; M represents an ion, chosen from aluminium, calcium, lithium, magnesium, potassium, sodium, zinc or their mixture; Z represents CR4; R4 is chosen from hydrogen, halogen, alkyl, alkylaryl and XYR5; R5 is chosen from aryl, substituted aryl, heteroaryl and substituted heteroaryl; R6 and R7 are independently chosen from hydrogen and alkyl; n is an integer from 1 to 6; at least one of R1 and R2 represents XYR5, and at least one of X and Y represents (CR6R7)n. The invention also pertains to the method of increasing concentration of D-serine and/or reducing concentration of toxic products of D-serine oxidation under the effect of DAAO in mammals, involving introduction into a subject of a therapeutically effective amount of a formula I compound, to the method of treating schizophrenia, treating or preventing loss of memory and/or cognitive ability, to the method of improving learning ability, method of treating neuropathic pain, as well as to a pharmaceutical composition, with DAAO inhibitory activity, based on these compounds.

EFFECT: obtained are new compounds and a pharmaceutical composition based on these compounds.

27 cl, 4 tbl, 72 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to novel compounds of the formula (I): wherein R1 represents halogen atom; R2 represents halogen atom; R3 represents (C1-C4)-alkyl; X represents nitrogen atom (N) or -CH; n = 0-3 under condition that when X represents -CH then n= 1 at least. Also, invention relates to novel compounds of the formula (II): wherein R1 represents halogen atom; R2 represents halogen atom; R3 represents hydrogen atom (H) or (C1-C4)-alkyl; X represents N or -CH; n = 0-3 under condition that when X represents -CH then n = 1 at least. Also, invention relates to a method for synthesis of compound of the formula (I), a method for synthesis of compound of the formula (II) and to a method for synthesis of compound of the formula (III) given in the invention description. Also, invention describes intermediate compounds of the formula (4) given in the invention description. Invention provides synthesis of novel biologically active compounds that can be used as insecticides, and a method for their synthesis.

EFFECT: valuable properties of compounds.

24 cl, 3 tbl, 19 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to derivatives of adamantine, in particular, to a new method for preparing adamant-1-yl-containing azoles of the general formula I-VIII: wherein R1 means ; R2 means ; R3 means ; R4 means ; R5 means ; R6 means ; R7 means , and R8 means . Indicated derivatives of adamantine are semifinished products used in synthesis of biologically active substances. Proposed method for preparing these compounds involves using a new method for synthesis of adamant-1-yl-containing azoles that includes the addition reaction of azoles: 2-methylimidazole, 3(5)-methylpyrazole and 4-methylpyrazole, 3,4-dinitropyrazole, 1,2,4-triazole, 3-methylpyrazole, 3-nitro-1,2,4-triazole and 5-methyltetrazole to 1,3-dehydroadamantane in the mole ratio of 1,3-dehydroadamantane to azole = 1:1 in diethyl ether medium at temperature 100°C for 4-5 h.

EFFECT: improved preparing method.

8 ex

FIELD: organic chemistry, chemical technology, herbicides.

SUBSTANCE: invention describes new substituted derivatives of pyrazole of the general formula (I): wherein n = 0 or 1; group A represents independently hydrogen atom, alkyl group with 1-4 carbon atoms, halogenalkyl group with 1-4 carbon atoms, cycloalkyl group with 3-6 carbon atoms or phenyl group having substituting groups optionally; group D represents hydrogen atom, alkyl group with 1-4 carbon atoms, halogenalkyl group with 1-4 carbon atoms, alkenyl group with 2-4 carbon atoms, alkoxy-group with 1-4 carbon atoms, cycloalkyl group with 3-6 carbon atoms, halogen atom, alkoxycarbonyl group with 1-4 carbon atoms, alkylsulfonyl group with 1-4 carbon atoms or phenyl group; group E represents hydrogen atom, halogen atom or phenyl group; groups R1 and R2 both represent halogen atom; group R3 represents hydrogen atom, alkyl group with 1-4 carbon atoms, halogenalkyl group with 1-4 carbon atoms, alkenyl group with 2-4 carbon atoms, alkynyl group with 2-4 carbon atoms or benzyl group; groups R4 and R5 are similar or different and each represents hydrogen atom, alkyl group with 1-4 carbon atoms, halogenalkyl group with 1-4 carbon atoms, cycloalkyl group with 3-8 carbon atoms that can be substituted with alkyl group with 1-4 carbon atoms, alkenyl group with 2-4 carbon atoms, alkynyl group with 2-4 carbon atoms, cyanomethyl group or phenyl group; or each R4 and R5 group means benzyl group; or each R4 and R5 group represents α- or β-phenethyl group having substituting groups at benzyl ring optionally. Indicated substituting groups represent alkoxy-groups with 1-4 carbon atoms wherein indicated substituting groups substitute hydrogen atom at the arbitrary positions 0-2 of the benzyl ring; or groups R4 and R5 form in common 5-membered or 6-membered aliphatic ring wherein the indicated ring can be substituted with alkyl groups with 1-4 carbon atoms and indicated ring can comprise one or two heteroatoms chosen from nitrogen oxygen and sulfur atom, and a method for their preparing. Also, invention describes herbicide compositions based on compound of the formula (I). Invention provides preparing herbicide compositions showing the strong herbicide effect and broad herbicide spectrum of their effect.

EFFECT: improved preparing method, valuable properties of derivatives and compositions.

7 cl, 6 tbl, 3 ex

The invention relates to biphenylamine General formula I

< / BR>
and their salts, where R1means H or F; R2means H, halogen, C1-C4-alkyl; R3means of CH3; connection I use for combating phytopathogenic fungi

The invention relates to new derivatives of 1-methyl-5-chloropyrazole General formula where R is CH2Cl, CF3, 4-CLC6H4, 3-NO2C6H4that shows antibacterial activity

FIELD: chemistry.

SUBSTANCE: invention relates to novel malononitryl derivatives of formula (I), which can be applied to fight pest insects. In formula (I) R1 represents hydrogen atom; R2 represents hydrogen atom; R represents hydrogen atom; R4 represents C1-C5-alkyl group substituted with at least one halogen atom, C2-C5-alkenyl group; R5 represents hydrogen atom, halogen atom, C1-C5-alkyl group; at least one of X1, X2 and X3 values represents CR6, the other represent nitrogen atoms; R represents hydrogen atom, halogen atom, cyanogroup, nitrogroup, formyl group, C1-C5-alkyl group optionally substituted with at least one halogen atom, C1-C5-alkyltiogroup, substituted with at least one halogen atom, C2-C6-alkylcarbonyl group substituted with at east one halogen atom, C2-C5-alkoxycarbonyl group or group (CH2)mQ, where m = 0, and Q stands for phenyl; and in case when one of R5 and R6 is bonded with two atoms in adjacent positions or two R6 are bonded with two atoms in adjacent positions, they can be bonded to each other in end positions with formation of C2-C6-alkandiyl group, or C4-C6-alkenediyl group. Invention also relates to composition and method used to fight pest-insects.

EFFECT: obtaining novel malononitryl derivatives of formula (I), which can be applied to fight pest-insects.

11 cl, 90 ex

FIELD: chemistry.

SUBSTANCE: invention relates to new compounds with general formula (I) , where R1 and R2 are independently chosen from hydrogen, halogen, nitro, alkyl, alkylaryl and XYR5; X and Y are independently chosen from O and (CR6R7)n; R3 represents hydrogen, alkyl or M; M represents an ion, chosen from aluminium, calcium, lithium, magnesium, potassium, sodium, zinc or their mixture; Z represents CR4; R4 is chosen from hydrogen, halogen, alkyl, alkylaryl and XYR5; R5 is chosen from aryl, substituted aryl, heteroaryl and substituted heteroaryl; R6 and R7 are independently chosen from hydrogen and alkyl; n is an integer from 1 to 6; at least one of R1 and R2 represents XYR5, and at least one of X and Y represents (CR6R7)n. The invention also pertains to the method of increasing concentration of D-serine and/or reducing concentration of toxic products of D-serine oxidation under the effect of DAAO in mammals, involving introduction into a subject of a therapeutically effective amount of a formula I compound, to the method of treating schizophrenia, treating or preventing loss of memory and/or cognitive ability, to the method of improving learning ability, method of treating neuropathic pain, as well as to a pharmaceutical composition, with DAAO inhibitory activity, based on these compounds.

EFFECT: obtained are new compounds and a pharmaceutical composition based on these compounds.

27 cl, 4 tbl, 72 ex

FIELD: chemistry.

SUBSTANCE: described are 2,4,6-phenyl-substituted cyclic ketoenols of formula (I, in which W, X, Y and CKE are given in invention formula. Also described are esters of acylamino acids of formula (II), substituted derivatives of phenylacetic acid of formula (XXIX), (XXVII), (XXXI), which are intermediate compounds for obtaining formula (I) compound.

EFFECT: obtaining herbicidal preparation containing combinations of biologically active substances, including (a), formula (I) compound and (b') improving compatibility with cultural plants mefenpyr-diethyl, with weight ratio 5-1:1-7.7.

9 cl, 46 tbl, 36 ex

FIELD: chemistry, pharmacology.

SUBSTANCE: claimed invention relates to compounds of formula (I) or their pharmaceutically acceptable salts, where Q represents optionally substituted with 1-3 substituents, determined in formula, phenyl or pyridyl or pyrodazinyl; R2 represents C1-6alkyl or aminogroup, determined in item 1 of formula or C1-6alkyl, substituted with said aminogroup; bond between oxygen atom O* and adjacent carbon atom C1 or (i) is double bond, which determines carbonyl group [C(=O)], where R6 represents C1-6alkyl or cyclopropyl; or (ii) represents simple bond, where, in case of simple bond, said oxygen atom O*, is in addition bound to group R6 and, taken together with R6 and with adjacent nitrogen atom, determines optionally substituted with C1-6alkyl, oxadiazolyl ring, bond between C1 and adjacent nitrogen atom being double bond.

EFFECT: obtaining medications which are useful in obtaining medications for treatment of conditions connected with p38 kinase and/or in obtaining medications for treatment of inflammatory diseases or conditions in patient.

8 cl, 6 tbl, 88 ex

FIELD: chemistry, pharmacology.

SUBSTANCE: invention relates to novel compounds -acidified arylcycloalkylamins of formula I in any of their stereoisomeric forms or in form of their mixture in any ratio, or their pharmaceutically acceptable salts, where in formula I : R1 represents aryl, not obligatory substituted with one or two similar or different substitutes, selected from group that includes C1-C6-alkyl and halogen; R2 represents aryl or heteroaryl, which represents residue of 5-6-member aromatic monocyclic heterocycle, containing 1-2 nitrogen atoms as heteroatom and/or 1 sulfur atom or oxygen atom, or residue of 9-10-member aromatic bicyclic heterocycle, containing 1-2 nitrogen atoms as heteroatom, each of which is unsubstituted or contains 1-3 similar or different substitutes, selected from group, consisting of halogens, NH2, unsubstituted C1-C10-alkyl, C1-C10 -alcoxy, C1-C10-alkylamino and di(C1-C10-alkyl)amino, and at least monosubstituted C1-C10-alkyl, etc., n represents 1, 2, 3 or 4. Invention relates to pharmaceutical composition, stimulating expression of endothelial NO synthase, based on said compounds, as well as application of compounds of formula I for production of medication for stimulating expression of endothelial NO-synthase and for treatment of such cardiovascular diseases as atherosclerosis, thrombosis, coronary artery disease, hypertension and impaired cardiac function.

EFFECT: invention ensures enhancing composition and treatment method efficiency.

9 cl, 2 tbl, 41 ex

FIELD: chemistry.

SUBSTANCE: aim of the invention is to create a method of obtaining a compound with general formula I , in which R1 represents a hydrogen atom or halogen or (C1-C4)alkene group; R2, R3, R4, R5, R6, R7 each independently represents a hydrogen atom or halogen or (C1-C4)alkene, (C1-C4)alkoxy, trifluoromethyl group as well as its salts. The proposed method involves reaction of a pentane derivative with formula X-(CH2)5-X'(II), in which each of X and X' independently represent a halogen atom or YSO2O- group, in which Y represents (C1-C4)alkene, (C1-C4)perfluoroalkene, phenyl group, unsubstituted or substituted with methyl, chloro- or a nitro- group, and the corresponding derivative of pyrazole-3-carbohydrazide. The invention also pertains to the method of obtaining N-piperidino-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxamide (rimonabant) and its salts.

EFFECT: development of an alternative method of obtaining formula I compounds and, in particular, pure rimonabant, which shows activity in clinic in obesity and smoking addiction.

11 cl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention refers to the method of preparation of 3-halogen-4.5-dihydro-1H-pyrasol compound of the formula , it includes interreaction with HX1of other 4.5-dihydro-1H-pyrasol compound of the formula , in which X1 is halogen and R3, R4, Z, n and X2 have values given in the description. The invention also describes preparation of the compounds of the formula , in which X1, R3, R6, R7, R8a, R8b and n have values, which are indicated in the description, in terms of the formula (Ia) of the compound, prepared according to p.1 of the invention formula.

EFFECT: development of the alternative method of preparation of the compounds with using reagent of relatively low price.

9 cl, 1 tbl, 4 ex, 9 dwg

FIELD: chemistry.

SUBSTANCE: the said invention relates to о-cyclopropylcarboxanilides of general formula (I) , where Het stands for pyrrolyl, pyrazolyl or thiazolyl, each being substituted with R4, R5 and R6 groups; R1, RЗ stand for hydrogen or halogen; R3 stands for С2-12 alkyl, С3-12 cycloalkyl, С3-12 cycloalkyl substituted with С1-3 alkyl, phenyl or halogen-substituted phenyl; and R4, R5 and R6 are independently selected from hydrogen, halogen, С1-4 alkyl or С1-4 haloalkyl, provided that at least one of R4, R5 and R6 is other than hydrogen. Intermediates used in synthesis of I, as well as antimicrobial composition and methods for control and prevention of cultivated plants' infection with phytopathogenic microorganisms are described.

EFFECT: compounds can be used to protect plants from being infected with phytopathogenic microorganisms.

8 cl, 7 tbl, 12 ex

FIELD: organic chemistry, fungicides.

SUBSTANCE: invention describes pyrazolylcarboxanilides of the formula (I) wherein R means difluoromethyl or trifluoromethyl group; R1 and R2 mean independently of one another halogen atom or (C1-C6)-alkyl; R3 means fluorine atom, and agent and method for control of undesirable fungi using compounds of the formula (I), and novel intermediate substances - derivatives of aniline and halogenpyrazolcarboxanilides. Compounds of the formula (I) elicit fungicide properties and can be used in protection of plants.

EFFECT: valuable properties of compounds and agent.

15 cl, 8 tbl, 10 ex

FIELD: organic chemistry, insecticides.

SUBSTANCE: invention relates to compounds of the formula (1) , their N-oxides and salts that can be used in agriculture wherein values A, B, J, R1, R3, R4 and n are given in the invention claim. Also, invention describes a method for control of arthropoda pests to provides high productivity that comprises applying the effective dose of compound of the formula (1) on arthropoda pests and in medium of their habitation, and a the composition with arthropocide activity comprising compounds of the formula (1).

EFFECT: valuable properties of compounds and composition.

23 cl, 34 tbl, 759 ex

FIELD: organic chemistry, fungicides.

SUBSTANCE: invention describes pyrazolylcarboxanilides of the formula (I) wherein R means difluoromethyl or trifluoromethyl group; R1 and R2 mean independently of one another halogen atom or (C1-C6)-alkyl; R3 means fluorine atom, and agent and method for control of undesirable fungi using compounds of the formula (I), and novel intermediate substances - derivatives of aniline and halogenpyrazolcarboxanilides. Compounds of the formula (I) elicit fungicide properties and can be used in protection of plants.

EFFECT: valuable properties of compounds and agent.

15 cl, 8 tbl, 10 ex

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