13-substituted derivatives milbemycin, obtaining them and their use against insects and other pests

 

Describes the 13-substituted derivatives milbemycin General formula (I):

and their salts,

where R1represents methyl group, ethyl group, sec-boutelou group; R2represents a hydrogen atom or alkyl group with 1-6 carbon atoms; R3represents hydrogen, acetyl group, pentanoyl group and alkylsulfonyl group; or R2and R3together with the nitrogen atom to which they are attached, form a 2-oxazolidinone-3-ilen group; and the group and, together with the carbon atom to which it is attached, form a 3-6-membered cycloalkyl group. Describes 13-[1-(4-methoxyacetophenone)cyclopentanecarboxylate]-5-hydroxymelatonin And4or its salt, 13-[1-(4-methoxyacetophenone)cyclopentanecarboxylate]-5-hydroxymelatonin And3or its salt. The presented composition, method of protecting plants or animals from damage caused by parasites. These compounds have anthelmintic, acaricidal and insecticidal activity. 5 S. and 26 C.p. f-crystals, 10 PL.

Description text in facsimile form (see graphic part).

Formula izaberete the R1represents methyl group, ethyl group or second-boutelou group;

R2represents a hydrogen atom or alkyl group with 1-6 carbon atoms;

R3represents a hydrogen atom, acetyl group, which optionally can be substituted by 1-3 substituents selected, independently, from among the substituents (which are defined below), pentanoyl group and alkylsulfonyl group in which the alkyl part contains 1 to 6 carbon atoms, or

R2and R3together with the nitrogen atom to which they are attached, form a 2-oxazolidinone-3-ilen group

group and, together with the carbon atom to which it is attached, form a 3-6-membered cycloalkyl group;

substituents And are selected from the group consisting of: halogen atoms, cyano groups, hydroxyl groups, alkoxygroup with 1-6 carbon atoms, amino group, substituted alkyl group with 1-6 carbon atoms and acetyl group, and 2-oxopyrrolidin group,

or its salt, acceptable for agriculture or veterinary medicine.

2. The compound of formula (I) or its salt, acceptable for agriculture or veterinary medicine under item 1, where R1represents methyl group or ethyl group.

3. Connect dstanley a hydrogen atom or alkyl group with 1-3 carbon atoms.

4. The compound of formula (I) or its salt, acceptable for agriculture or veterinary medicine under item 1 or 2, where R2represents a hydrogen atom or methyl group.

5. The compound of formula (I) or its salt, acceptable for agriculture or veterinary medicine under item 1 or 2, where R2represents a hydrogen atom.

6. The compound of formula (I) or its salt, acceptable for agriculture or veterinary medicine according to any one of paragraphs.1-5, where R3represents a hydrogen atom, acetyl group, which optionally may be substituted by 1 or 2 substituents selected, independently, from the group consisting of halogen atoms, cyano groups, hydroxyl groups, alkoxygroup (1-3 carbon atoms), amino groups substituted by alkyl group with 1-3 carbon atoms and acetyl group, and 2-oxopyrrolidin group, pentanoyl group or alkylsulfonyl group in which the alkyl part contains 1-3 carbon atoms.

7. The compound of formula (I) or its salt, acceptable for agriculture or veterinary medicine according to any one of paragraphs.1-5, where R3represents a hydrogen atom, acetyl group, hydroxyazetidine group, methoxyacetyl group, ethoxyacetylene group or trifluoracetyl group.

8. Compound f which is methoxyacetyl group.

9. The compound of formula (I) or its salt, acceptable for agriculture or veterinary medicine under item 1 or 2, where R2and R3together with the nitrogen atom to which they are attached, form a 2-oxazolidinone-3-ilen group.

10. The compound of formula (I) or its salt, acceptable for agriculture or veterinary medicine according to any one of paragraphs.1-9, where the group and, together with the carbon atom to which it is attached, forms cyclobutyl group or cyclopentyl group.

11. The compound of formula (I) or its salt, acceptable for agriculture or veterinary medicine according to any one of paragraphs.1-9, where the group and, together with the carbon atom to which it is attached, forms cyclopentyloxy group.

12. The compound of formula (I) or its salt, acceptable for agriculture or veterinary medicine under item 1, where

R1represents methyl group, ethyl group or second-boutelou group;

R2represents a hydrogen atom or alkyl group with 1-3 carbon atoms;

R3represents a hydrogen atom, acetyl group, which optionally may be substituted by 1 or 2 substituents selected, independently, from the group consisting of halogen atoms, cyano groups, hydroxyl groups, alkoxygroup (with 1-3 atoms uperoleia group, pentanoyl group, alkylsulfonyl group in which the alkyl part contains 1-3 carbon atoms,

or R2and R3together with the nitrogen atom to which they are attached, form a 2-oxazolidinone-3-ilen group, and

group and, together with the carbon atom to which it is attached, forms cyclobutyl group or cyclopentyl group.

13. The compound of formula (I) or its salt, acceptable for agriculture or veterinary medicine under item 12, where both R2and R3cannot simultaneously represent hydrogen atoms.

14. The compound of formula (I) or its salt, acceptable for agriculture or veterinary medicine under item 1, where

R1represents methyl group or ethyl group;

R2and R3together with the nitrogen atom to which they are attached, form a 2-oxazolidinone-3-ilen group, and

group and, together with the carbon atom to which it is attached, forms cyclobutyl group or cyclopentyl group.

15. The compound of formula (I) or its salt, acceptable for agriculture or veterinary medicine under item 1, where

R1represents methyl group or ethyl group;

R2and R3together with the nitrogen atom to which they are attached, education will formed cyclopentyloxy group.

16. The compound of formula (I) or its salt, acceptable for agriculture or veterinary medicine under item 1, where

R1represents methyl group or ethyl group;

R2represents a hydrogen atom or alkyl group with 1-3 carbon atoms;

R3represents a hydrogen atom, acetyl group, which optionally may be substituted by 1 or 2 substituents selected, independently, from the group consisting of halogen atoms, cyano groups, hydroxyl groups, alkoxygroup (1-3 carbon atoms), amino group, substituted alkyl group with 1-3 carbon atoms and acetyl group, and 2-oxopyrrolidin group, pentanoyl group and alkylsulfonyl group in which the alkyl group contains 1-3 carbon atoms, and

group and, together with the carbon atom to which it is attached, forms cyclobutyl group or cyclopentyl group.

17. The compound of formula (I) or its salt, acceptable for agriculture or veterinary medicine under item 1, where

R1represents methyl group or ethyl group;

R2represents a hydrogen atom or methyl group;

R3represents a hydrogen atom or acetyl group, optionally substituted Deputy SEL is amino, substituted alkyl group with 1-3 carbon atoms and acetyl group, and 2-oxopyrrolidin group, and

group and, together with the carbon atom to which it is attached, forms cyclopentyloxy group.

18. The compound of formula (I) or its salt, acceptable for agriculture or veterinary medicine under item 1, where

R1represents methyl group or ethyl group;

R2represents a hydrogen atom;

R3represents a hydrogen atom, acetyl group, hydroxyazetidine group, methoxyacetyl group, ethoxyacetylene group or trifluoracetyl group and

group and, together with the carbon atom to which it is attached, forms cyclopentyloxy group.

19. The compound of formula (I) or its salt, acceptable for agriculture or veterinary medicine under item 1, where

R1represents methyl group or ethyl group;

R2represents a hydrogen atom;

R3is methoxyacetyl group and

group and, together with the carbon atom to which it is attached, forms cyclopentyloxy group.

20. The compound of formula (I) under item 1, selected from the group including:

13-[1-(4-AMINOPHENYL)cyclopentanecarboxylate]-5-hydroxymelatonin And4;

13-[1-(4-hydroxyethylaminophenol)

cyclopentanecarbonyl]-5-hydroxymelatonin And4;

13-[1-(4-methoxyacetophenone)

cyclopentanecarbonyl]-5-hydroxymelatonin And4;

13-[1-(4-methanesulfonylaminoethyl)

cyclopentanecarbonyl]-5-hydroxymelatonin And4;

13-[1-(4-methoxyacetophenone)

cyclopentanecarbonyl]-5-hydroxymelatonin And3;

13-[1-(4-methanesulfonylaminoethyl)

cyclopentanecarbonyl]-5-hydroxymelatonin And3;

13-[1-(4-methoxyacetophenone)cyclobutanecarbonyl]-5-hydroxymelatonin And4;

13-[1-(4-methanesulfonylaminoethyl)

cyclobutanecarbonyl]-5-hydroxymelatonin And4;

13-{1-[4-(N-acetyl-N-methylamino)phenyl]

cyclopentanecarbonyl}-5-hydroxymelatonin And4,

or its salt, acceptable for agriculture or veterinary medicine.

21. 13-[1-(4-Methoxyacetophenone) cyclopentanecarboxylate]-5-hydroxymelatonin And4or its salt, acceptable for agriculture or veterinary medicine.

22. 13-[1-(4-Methoxyacetophenone) cyclopentanecarboxylate]-5-hydroxymelatonin And3or its salt, acceptable for agriculture or veterinary medicine.

23. Anthelminthic, aka the e in mixture with acceptable agricultural or veterinary carrier or diluent, where the specified connection selected from the group consisting of compounds of the formula (I) and their salts acceptable for agriculture or veterinary medicine according to any one of paragraphs.1-22.

24. The composition according to p. 23 suitable for veterinary use against ticks, worms or insects, parasitic on mammals.

25. The composition according to p. 23, which is suitable for use as an insecticide against cat fleas (Ctenocephalides felis) and dog fleas (Ctenocephalides canis).

26. Method of protecting plants or animals from damage caused by parasites selected from the group consisting of mites, worms and insects, comprising applying an active compound to said plants or animals, or parts or reproductive material of these plants or to the locus of these plants or animals or parts or reproductive material of these plants, where the active compound selected from the group consisting of compounds of the formula (I) and their salts acceptable for agriculture or veterinary medicine according to any one of paragraphs.1-22.

27. The method according to p. 26 to protect non-human animals from damage ticks, worms or insects on these animals.

28. The method according to p. 26 to protect animals from Povray (I) or its salt, acceptable for agriculture or veterinary medicine according to any one of paragraphs.1-26, for use as a remedy for protection of animals from damage caused by parasites selected from the group consisting of mites, worms and insects.

30. The compound of formula (I) or its salt, acceptable for agriculture or veterinary medicine for use on p. 29, where these parasites are ticks, worms or insects on animals.

31. The compound of formula (I) or its salt, acceptable for agriculture, horticulture, pharmacy or veterinary medicine for use on p. 29, where these parasites are cat fleas (Ctenocephalides felis) or dog fleas (Ctenocephalides canis).

 

Same patents:

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< / BR>
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,

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FIELD: agriculture.

SUBSTANCE: invention describes a method for feeding potato and tomato with 6-benzylaminopurine an aqueous solution taken in the concentration 10-4 M and growing pants up to preparing harvest according to technology accepted for the culture crop. Invention proposes 3-fold treatment of plants for vegetation: at the lateral branching phase, at onset of forming economically value organs and immediately after the growth termination. Method provides the effective enhancing the productivity of the most important vegetable crops - tomato and potato.

EFFECT: improved enhancing method.

6 tbl, 4 ex

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