Antibiotic substances B-41, their production and their use as insecticides and acaricides

Claim 1

A process for producing antibiotic substances B-41-A 1 , B-41-A 2 , B-41-A 3 , B-41-A 4 , B-41-B 1 , B-41-B 2 , B-41-B 3 , B-41-C 1 and B-41-C 2 which comprises culturing Streptomyces strain B-41-146 (NRRL 5739) and mutants thereof, wherein i. substance A 1 is represented by the formula ##STR5## ii. substances A 3 , A 4 , B 2 and B 3 are represented by the formula ##STR6## wherein ______________________________________ substance R.sub.1 R.sub.2 R.sub.3 ______________________________________ A.sub.3 H CH.sub.3 CH.sub.3 A.sub.4 H CH.sub.3 C.sub.2 H.sub.5 B.sub.2 CH.sub.3 CH.sub.3 CH.sub.3 B.sub.3 CH.sub.3 CH.sub.3 C.sub.2 H.sub.5 ______________________________________ wherein R 1 represents a hydrogen atom or methyl, R 2 represents methyl and R 3 represents methyl or ethyl; iii. substances C 1 and C 2 are represented by the formula ##STR7## wherein R 1 represents a hydrogen atom, R 2 represents a pyrroyloxymethyl group of the formula ##STR8## and R 3 represents a methyl group of an ethyl group; iv. substance B-41-A 2 is a colorless amorphous powder form which is difficultly soluble in water and easily soluble in n-hexane, benzene, acetone, ethanol and chloroform and has a molecular formula of C 38 H 56 O 10 , a composition of 71.73% carbon and 8.26% hydrogen and the following properties; molecular weights of 672.1 obtained by an osmometric method in acetone and of 672 according to mass spectrum; a specific rotatory power of D 20 = + 54° obtained with the concentration of a sample of 5 mg./2ml. and the length of a layer of 10 cm. in acetone; no pKa at a pH ranging from 2 to 12; absorption maximum in the ultraviolet region of the spectrum at 245 mμ; characteristic absorption bands in the infrared region shown in FIG. 11; nuclear magnetic resonance spectrum in (CD 3 ) 2 CO shown in FIG. 20; main peaks of the mass spectrum 672, 181, 153 and 151 obtained under the conditions of 75 eV at ionization room temperature of 200° C. and a sample temperature of 120°-190° C.; and the following color reactions according to a thin layer chromatography; yellow to iodine/chloroform, negative to ninhydrin, reddish purple to sulfuric acid and yellow to potassium permanganate; and v. substance B-41-B 1 is a colorles substance which is difficultly soluble in water and easily soluble in n-hexane, benzene, acetone, ethanol and chloroform and has a molecular formula of C 39 H 58 O 10 , a composition of 68.00% carbon and 8.32% hydrogen and the following properties; a melting point of 176°-178° C.; molecular weights of 629.5 obtained by an osmometric method in acetone and of 686 according to mass spectrum; a specific rotatory powder of D 20 = +75° obtained with the concentration of a sample of 5 mg./2 ml. and the length of a layer of 10 cm. in acetone; no pKa at a pH ranging from 2 to 12; absorption maximum in the ultraviolet region of the spectrum at 245 mμ; characteristic absorption bands in the infrared region shown in FIG. 14; nuclear magnetic resonance spectrum in (CD 3 ) 2 CO shown in FIG. 23; main peaks of the mass spectrum 686, 414, 195, 167, 151 and 125 obtained under the conditions of 75 eV at ionization room temperature of 200° C. and a sample temperature of 120°-190° C.; and the following color reactions according to a thin layer chromatography, yellow to iodine/chloroform, negative to ninhydrin, reddish purple to sulfuric acid and yellow to potassium permanganate.