| Identification | Back Directory | [Name]
Polyoxin | [CAS]
11113-80-7 | [Synonyms]
POLYOXINS
1-[(2R,3R,4S,5R)-5…
1-[(2R,3R,4S,5R)-5-(1-amino-2-oxoethyl)-3,4-dihydroxyoxolan-2-yl]-2,4-dioxopyrimidine-5-carboxylic acid | [Molecular Formula]
C11H13N3O8 | [MOL File]
11113-80-7.mol | [Molecular Weight]
315.236 |
| Hazard Information | Back Directory | [Description]
Polyoxin was found in the culture broth of Streptomyces cacaoi var. asoensis by Suzuki et al. in 1965. It consists of several closely related components, A through O, and shows activity against phytopathogenic fungi by inhibition of cell-wall chitin synthesis. Polyoxin has been used in agriculture against fungal infections, especially Alternaria leaf spot in vegetables and fruits. | [Uses]
The fungicidal activities of polyoxins reported on many
plant pathogens, including Alternaria spp. and Rhizoctonia
zoctonia spp. (24,25).
Polyoxin B is used for control of Alternaria spp.
and powdery mildews in apples and pears; Botrytis
cinerea in vines and aubergines; powdery mildews in
roses, chrysanthemums, and melons; blight of carnation;
powdery mildew, brown spot, and gray mold in tobacco;
powdery mildew and gray mold in strawberries; leaf mold,
early blight, and gray mold in tomatoes; powdery mildew,
gray mold, Sclerotinia erotinia spp. rot, and Corynespora
melonis in cucumbers; Alternaria spp. blight in carrots;
purple blotch in leeks. Patent: JP 493008 Formulation
types: WP; EC; SG. Mixes with captan; oxine-copper;
iminoctadine triacetate. Compatibility: Incompatible with
alkaline materials. Tradename “Polyoxin AL.”
Polyoxin D zinc salt is used for control of sheath
blight (Rhizoctonia solani) in rice; canker in apples
and pears; Rhizoctonia solani, Drechslera spp., Bipolaris
spp., Curvularia spp., and Helminthosporium spp. in
lawn turf. Formulation types: WP; PA. Mixes with
thiram; propiconazole. Compatibility: Incompatible with
alkaline materials. Tradenames “Kakengel” (zinc salt);
“Polyoxin Z” (zinc salt); “Stopit.”
Application of polyoxins can be made at any growth
stage of rice plants without causing phytotoxicity even at
800-ppm application. Foliar sprays of 200 ppm of polyoxins
have produced no phytotoxicity on all the other crops
tested. | [Metabolism]
Polyoxin B causes a marked abnormal swelling on germ
tubes of spores and hyphal tips in Alternaria spp.,
and this makes the pathogen noninfectious. In a cellfree
system of Neurospora crassa, polyoxin D inhibits
the incorporation of N-acetyl-glucosamine (GlcNAc) into
chitin in a competitive manner between UDP-GlcNAc
and polyoxin D; the pyrimidine nucleoside moiety of the
antibiotics was shown to fit into the binding site of the
enzyme protein, and the carbamoylpolyoxamic acid moiety
of polyoxins stabilizes the polyoxin-enzyme complex (26).
Polyoxin-resistant strains of A. alternata were recognized
in pear orchards after several years of intensive
use of the antibiotics. The resistance was suggested to be
caused by a lowered permeability of the antibiotic through
the cell membrane into the site of chitin synthesis (27). | [Toxicity evaluation]
Acute oral LD50 of polyoxin B for male rats 21, female
rats 21.2, male mice 27.3, and femalemice 22.5 g/kg. Acute
percutaneous LD50 for rats >2 g/kg. Nonirritant to mucous
membranes and skin (rats). Inhalation LD50 (6 h) for rats
10 mg/L air. NOEL (2 y) for rats and mice >48-g/kg diet.
Toxicity class EPA (formulation) IV.
Acute oral LD50 of polyoxin D for male rats and
female rats >9.6 g/kg. Acute percutaneous LD50 for rats
>750 mg/kg. Inhalation LD50 (4 h) for male rats 2.44,
female rats 2.17 mg/L air. NOEL (2 y) for rats >50, mice
>40 g/kg diet. Toxicity class EPA (formulation) III (WP). |
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