Bafilomycin pesticides

• US 4,558,139 A
• Filed: 03/14/1984
• Issued: 12/10/1985
• Est. Priority Date: 03/23/1983
• Status: Expired due to Fees

• Current Assignee: Bayer AG
• Original Assignee: Bayer AG
• Inventors: Andrews, Peter, Reinecke, Paul, Brandes, Wilhelm, Schaller, Klaus, Stendel, Wilhelm, Zahner, Hans, Zoebelein, Gerhard, Holst, Hartwig, Werner, Gerhard, Hagenmaier, Hans-Paul, Drautz, Hannelore
• Primary Examiner(s): Fan, Jane T.
• Application Number:
  US06/589,380
• Time in Patent Office: 636 Days
• Field of Search: 549/271
• US Class Current: 549/271
• CPC Class Codes: A61P 33/10 Anthelmintics
• CPC Class Codes: C07H 7/06 Heterocyclic radicals
• CPC Class Codes: C12N 1/205 Bacterial isolates
• CPC Class Codes: C12P 19/02 Monosaccharides 2-ketogulonic acid C12P7/60
• CPC Class Codes: C12P 19/44 Preparation of O-glycosides, e.g. glucosides polysaccharides and not substituted disaccharides C12P19/04, C12P19/12
• CPC Class Codes: C12R 2001/465 Streptomyces

Abstract

Bafilomycins of the formula ##STR1## in which R¹ is hydrogen or CH₃, and

R² is hydrogen, or the group ##STR2## are produced by culturing certain streptomyces, e.g. Tu 1922, Tu 2437 and Tu 2599. Those wherein at least one of the OH groups is acylated are new. The compounds are pesticidally active.

Claims

1. Bafilomycin of the formula ##STR6## in which R is hydrogen or the acyl radical of a carboxylic acid having one to six carbon atoms,

R¹ is hydrogen or CH₃, and

R² is hydrogen, the acyl radical of a carboxylic acid having one to six carbon atoms or the group ##STR7## at least one of R and R² being the radical of a carboxylic acid acyl.

2. A Bafilomycin according to claim 1, in which the acyl radical is acetyl.

9. Bafilomycin according to claim 1, in which R and R¹ are hydrogen and R² is acetyl.

10. Bafilomycin according to claim 1, in which R and R² are acetyl and R¹ is hydrogen.

11. Bafilomycin according to claim 1, in which R is hydrogen, R¹ is methyl and R² is acetyl.

12. Bafilomycin according to claim 1, in which R and R² are acetyl and R¹ is methyl.

13. An insecticidal, arachnicidal, nematicidal or fungicidal composition comprising an insecticidally, arachnicidally, nematicidally or fungicidally effective amount of pure Bafilomycin according to claim 1 in admixture with a diluent.

3. A pure Bafilomycin of the formula ##STR8## in which R is hydrogen or the acyl radical of a carboxylic acid having one to six carbon atoms,

R¹ is hydrogen or CH₃, and

R² is hydrogen, the acyl radical of a carboxylic acid having one to six carbon atoms or the group ##STR9##

4. A Bafilomycin according to claim 3, in which the acyl radical is acetyl.

5. Bafilomycin A₁ according to claim 3 in which R, R¹ and R² are hydrogen and having the following properties:

Appearance;

colorless amorphous powder,

Melting point;

98°

-106°

C. (decomposition),

Solubility;

readily soluble in methanol,

readily soluble in chloroform,

sparingly soluble in water,

Thin-layer chromatogram (silica gel);

CHCl₃ ;

CH₃ OH (9;

1 parts by volume),

Rf;

0.51,

Ethyl methyl ketone;

CHCl₃ (1;

1 parts by volume) Rf;

0.42,

Ethyl methyl ketone;

Rf;

0.86,

Acetone;

Rf;

0.91,

Molecular weight;

622,

Molecular formula (elemental analysis);

C₃₅ H₅₈ O₉,

Spectra;

UV;

FIG. 1,

IR;

FIG. 2,

NMR;

FIG. 3.

6. Bafilomycin A₂ according to claim 3 in which R and R² are hydrogen and R¹ is methyl, and having the following properties:

Appearance;

colorless amorphous powder,

Melting point;

116°

-119°

C. (decomposition),

Solubility;

readily soluble in methanol,

readily soluble in chloroform,

sparingly soluble in water,

Thin-layer chromatogram;

CHCl₃ ;

CH₃ OH (9;

1 parts by volume),

Rf;

0.52,

Ethyl methyl ketone;

CHCl₃ (1;

1 parts by volume) Rf;

0.42,

Acetone;

Rf;

0.91,

Molecular formula (elemental analysis);

C₃₆ H₆₀ O₉,

Spectra;

UV;

FIG. 4,

IR;

FIG. 5,

NMR;

FIG. 6,

Molecular weight;

636.

7. Bafilomycin B₁ according to claim 3 in which R and R¹ are hydrogen and R² is ##STR10## and having the following properties:

Appearance;

amorphous powder with an intense yellow color,

Melting point;

89°

-96°

C. (decomposition),

Solubility;

readily soluble in methanol,

readily soluble in chloroform,

readily soluble in pyridine,

soluble in ethyl acetate,

sparingly soluble in water,

Thin-layer chromatogram (silica gel);

CHCl₃ ;

CH₃ OH (9;

1 parts by volume),

Rf;

0.43,

Ethyl methyl ketone;

CHCl₃ (1;

1 parts by volume) Rf;

0.37,

Ethyl methyl ketone;

Rf;

0.78,

Acetone;

Rf;

0.76,

Molecular weight;

815,

Molecular formula (elemental analysis);

C₄₄ H₆₅ O₁₃ N,

Spectra;

UV;

FIG. 7,

IR;

FIG. 8,

NMR;

FIG. 9.

8. Bafilomycin B₂ according to claim 3, in which R is hydrogen, R¹ is methyl and R² is ##STR11##

14. An insecticidal, arachnicidal, nematicidal or fungicidal composition comprising an insecticidally, arachnicidally, nematicidally or fungicidally effective amount of pure Bafilomycin according to claim 3 in admixture with a diluent.

15. A method of combating insects, arachnids, nematodes or fungi which comprises administering thereto or to a habitat thereof an insecticidally, arachnicidally, nematicidally or fungicidally effective amount of Bafilomycin of the formula ##STR12## in which R is hydrogen or the acyl radical of a carboxylic acid having one to six carbon atoms,

R¹ is hydrogen or CH₃, and

R² is hydrogen, the acyl radical of a carboxylic acid having one to six carbon atoms or the group ##STR13##

16. The method according to claim 15, wherein the Bafilomycin is selected from the group consisting of Bafilomycins wherein

(a) R, R¹ and R² are hydrogen,

(b) R and R² are hydrogen and R¹ is methyl,

(c) R and R¹ are hydrogen and R² is ##STR14## (d) R is hydrogen, R¹ is methyl and R² is ##STR15## (e) R and R¹ are hydrogen and R² is acetyl, (f) R and R² are acetyl and R¹ is hydrogen

(g) R is hydrogen, R¹ is methyl and R² is acetyl, and

(h) R and R² are acetyl and R¹ is methyl.