2079-00-7

Usage

Uses

Used in Agriculture:
Blasticidin S is used as a fungicide for the control of rice blast (Pyricularia oryzae) by foliar application.
Used in Pharmaceutical Industry:
Blasticidin S is used as an antifungal agent with potent activity against various pathogens, making it a valuable asset in the development of treatments for fungal infections.
Used in Research and Development:
Blasticidin S is used as a marker for strain manipulations, aiding researchers in their work with various microorganisms and contributing to advancements in the field of microbiology.

Production Methods

Blasticidin S is produced by Streptomyces griseochromogenes, and has a wide range of antimicrobial activity (4). This antibiotic was utilized in the Far East beginning in 1961 against the rice blast pathogen Pyricularia oryzae, with effective control achieved at rates of 10–40 ppm (4).

Pharmacology

Inhibits protein synthesis both in eukaryotes and in prokaryotes (5,6). Interacts with ribosomal RNA in large subunit, interfering with the transpeptidation step. Inhibits cell-free protein synthesis in P. oryzae and Escherichia coli.

Metabolic pathway

Several blasticidin S-resistant microorganisms are found to produce blasticidin S deaminase which catalyzes the hydrolytic deamination of the cytosine moiety in blasticidin S to give a non-toxic deaminohydroxy derivative.

Metabolism

3H-blasticidin S administered to mice was excreted in the urine and feces within 24 h. Cytomycin and cytosin were identified as the main metabolites in and on rice plants, respectively (7). In soil, DT50 < 5 d. Metabolized to nontoxic deaminohydroxy blasticidin S by Aspergillus sp. and resistant Bacillus cereus. Novel deaminase and coding genes, BSD and bsr, were isolated as selectable marker genes for genetic engineering (8).

Toxicity evaluation

Acute oral LD50 for male rats: 56.8, female rats: 55.9, male mice: 51.9, and female mice: 60.1 mg/kg. Acute percutaneous LD50 for rats >500 mg/kg. Eye: severe irritation.

Degradation

Blasticidin-S is obtained as white needle crystals which are very soluble in water. The compound is stable in the pH range 5-7 but it is unstable under alkaline conditions. It is readily degraded by sunlight when on the surface of rice plants with the main degradation product being cytosine (2) (Yamaguchi et al., 1972) as shown in Scheme 1.

InChI:InChI=1/C17H26N8O5/c1-24(16(20)21)6-4-9(18)8-12(26)22-10-2-3-13(30-14(10)15(27)28)25-7-5-11(19)23-17(25)29/h2-3,5,7,9-10,13-14H,4,6,8,18H2,1H3,(H3,20,21)(H,22,26)(H,27,28)(H2,19,23,29)/t9?,10-,13+,14-/m0/s1

Upstream product

• 220144-84-3 dl-arginine hydrochloride 
• 19018-47-4 leucylblasticidin S 
• 2280-44-6 D-Glucose 
• 71-30-7 Cytosine 
• 74-79-3 L-arginine 
• 63-68-3 L-methionine 

Downstream Products

• 1860-84-0 cytosinine 

Relevant academic research and scientific papers

Reevaluation of the final steps in the biosynthesis of blasticidin S by Streptomyces griseochromogenes and identification of a novel self-resistance mechanism

The final steps in the biosynthesis of the antifungal peptidyl- nucleoside blasticidin S (3) have been revised to include a novel self- resistance mechanism wherein the previously proposed final precursor, demethylblasticidin S (7), is modified with a leucine residue yielding leucyldemethylblasticidin S (10) which exhibits reduced antibiotic activity. Methylation of 10 yields leucylblasticidin S (9) which can be exported from the bacterium and hydrolyzed to 3. Also disclosed is the finding of a blasticidin S N-acetyltransferase activity that may function to detoxify 3 and 7 inadvertently produced prior to export or which gain reentry to the cell. (C) 2000 Elsevier Science Ltd.

Stereochemistry of C-3 deoxygenation of sugar nucleosides: Formation of pentopyranine C from [3-2H]-D-glucose by Streptomyces griseochromogenes

Cytosylglucuronic acid (CGA) has previously been shown to be the first intermediate in the biosynthesis of the antibiotic blasticidin S (BS), produced by Streptomyces griseochromogenes. Addition of aminooxyacetic acid (AOAA), an inhibitor of pyridoxal phosphate/pyridoxamine phosphate-dependent transaminases, to 5. griseochromogenes fermentations led to substantial accumulations of CGA and pentopyranine C (PPNC, a shunt metabolite which has undergone decarboxylation at C-5′, deoxygenation at C-3′, and epimerization at C-4′) and to substantial reductions in the production of BS and N-demethylBS. In contrast, inhibitors of glutamine-dependent amidotransferases had little effect. [3-2H]-D-Glucose was fed to a fermentation of S. griseochromogenes containing arginine hydroxamate, an inhibitor of arginine biosynthesis, and a large quantity of cytosine-currently the best conditions for maximum production of CGA and PPNC. This yielded cytosyl[3′-2H]glucuronic acid, an 85:15 mixture of [3′-2Haxial]- and [3′-2Hequatorial]PPNC, and a small amount of a 46:54 mixture of [3′-2Haxial]- and [3′-2Hequatorial]pentopyranone (the immediate precursor to PPNC). The relationship of this C-3 sugar deoxygenation to blasticidin S biosynthesis and to the pyridoxamine phosphate-dependent CDP-4-keto-6-deoxy-D-glucose-3-dehydrase reaction which is central to cell-wall lipopolysaccharide biosynthesis of Gram-negative bacteria is discussed.

SUBSTITUTED SPIROCYCLIC KETOENOLS

The present invention relates to novel substituted spirocyclic ketoenols of the formula (I) in which W, X, Y, Z, A, B, D and G are as defined in the disclosure, to a plurality of processes for their preparation and to their use as pesticides, microbicides and herbicides.

Glyoxyl acid amides, method for producing them and their use for controlling harmful organisms

The invention relates to novel gloyoxylic acid amides, to a process for their preparation and to their use for controlling harmful organisms.

Use of oxabicyclo[2.2.1]heptane derivatives as pesticidal agents

7-oxabicyclo[2.2.1]heptane derivatives of formula (I) in which X, R1, R2, R3 and R4 have the meanings set forth in the specification, are very suitable for controlling undesired microorganisms and animal pests. New 7-oxabicyclo[2.2.1]heptane derivatives of formula (Ia) in which X, R1, R2, R3 and R14 have the meanings set forth in the specification, and a process for the preparation of the new compounds.

Triazolopyrimidines

The invention relates to novel triazolopyrimidines of the formula 1wherein X represents halogen, Y represents a hydrogen atom or halogen, and R has the meanings given in the disclosure, to a process for the preparation of the new compounds, and to their use as microbicides.

Heterocyclic fluoroalkenyl thioethers and the use thereof as pesticides(III)

The present invention relates to novel heterocyclic fluoroalkenyl thioethers of the formula (I) in which X represents hydrogen, halogen or alkyl, m represents integers from 3 to 10, n represents 0, 1 or 2, Y represents sulphur or oxygen, R1 represents halogen, represents in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkenyl, alkenyloxy, alkenylthio or alkylcarbonyl, represents optionally substituted cycloalkyl, represents optionally substituted aryl or represents optionally substituted heterocyclyl and R2 represents hydrogen, halogen, represents in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkenyl, alkenyloxy, alkenylthio or alkylcarbonyl, represents optionally substituted cycloalkyl, represents optionally substituted aryl or represents optionally substituted heterocyclyl, ?except for compounds where R1=alkyl, Y=oxygen and X=hydrogen, and to processes for their preparation and to their use as pesticides.

Heterocyclic fluoroalkenyl thioethers and the use thereof as pesticides (I)

The present invention relates to novel heterocyclic fluoroalkenyl thioethers of the formula (I) in which X represents hydrogen, halogen or alkyl, m represents integers from 2 to 10, n represents 0, 1 or 2, Y represents unsubstituted or substituted methylene and p represents 1, 2 or 3. and to processes for their preparation and to their use as pesticides.

Substituted imide derivatives

The present invention relates to novel substituted imide derivatives of the general formula (I) in which R1 represents optionally substituted cycloalkyl, R2 represents optionally substituted alkyl or optionally substituted cycloalkyl, R3 represents alkyl, alkoxy, alkylthio, amino, alkylamino or dialkylamino and R4 represents cyano or nitro, and to processes for their preparation and to their use for controlling animal pests and as herbicides.

Substituted 3-thiocarbamoylpyrazoles

The invention relates to novel substituted 3-thiocarbamoylpyrazoles of general formula (I), wherein m, n, R1, R2, R3and Ar have the meanings cited in the description. The invention further relates to methods for the production and use thereof as pesticides.