Kasugamycin

379.36

379.36

615-014-8

O957UYB9DY

DTXSID1040374

221

-5.75 (est)

2.0±0.1 g/cm3

203 deg C (dec)

585.9±60.0 °C at 760 mmHg

308.2±32.9 °C

1.738

In water, 1X10+6 mg/L at 25 deg C /Miscible/ (est)

<1.3X10-4 mm Hg at 25 deg C

pKa1 = 3.23 /carboxylic acid/; pKa2 = 7.73 /cyclic primary amine/; pKa3 = 11.0 /secondary amine/

Hydroxyl radical reaction rate constant = 2.34X10-10 cu cm/molec-sec at 25 °C (est)|Physicochemical properties of the technical grade compound (Kasugamycin hydrochloride hydrate). [Table#6189]

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

SOURCE DOMINATED: Kasugamycin was detected at 13 mg/cu m in air after application of 12 g/ha to a paddy field 750 ha in size, Niigata, Kysougase-mura, Japan(1). The study date ranged from August 8 through August 14, 1991(1).

LD50 Mouse dermal >10 g/kg|LD50 Mouse oral > 5000 mg/kg|LD50 Rat oral 11,400 mg/kg|LD50 Rat oral >5000 mg/kg /Kasugamycin hydrochloride hydrate, from table/|For more Non-Human Toxicity Values (Complete) data for KASUGAMYCIN (8 total), please visit the HSDB record page.

Kasugamycin's production may result in its release to the environment through various waste streams; it's use as a agricultural systemic fungicide and bactericide(1) will result in its direct release to the environment(SRC). Kasugamycin is not registered for use in the US; however, tolerances were established to cover imported produce from Mexico(2).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that kasugamycin is expected to have very high mobility in soil(SRC). The first and second pKas of kasugamycin are 3.23 (carboxylic acid) and 7.73 (cyclic primary amine)(3), indicating that this compound will exist as a zwitterion in the environment. Volatilization of kasugamycin from moist soil surfaces is not expected to be an important fate process because ionic compounds do not volatilize(4). Kasugamycin is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of <1.3X10-4 mm Hg(5). Biodegradation data were not available(SRC, 2006).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that kasugamycin is not expected to adsorb to suspended solids and sediment(SRC). The pKas of 3.23 (carboxylic acid) and 7.73 (cyclic primary amine)(3) indicate kasugamycin will exist as a zwitterion at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. According to a classification scheme(4), an estimated BCF of 3(SRC), from an estimated log Kow of -5.75(5), suggests that the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2006).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), kasugamycin, which has <1.3X10-4 mm Hg at °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase kasugamycin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1.6 hrs(SRC), calculated from its rate constant of 2.3X10-14 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase kasugamycin may be removed from the air by wet or dry deposition(SRC). Kasugamycin does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4).

The rate constant for the vapor-phase reaction of kasugamycin with photochemically-produced hydroxyl radicals has been estimated as 2.3X10-14 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.6 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Kasugamycin is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Kasugamycin does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(2).

An estimated BCF of 3 was calculated in fish for kasugamycin(SRC), using an estimated log Kow of -5.75(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of kasugamycin can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that kasugamycin is expected to have very high mobility in soil. The pKas of kasugamycin are 3.23 and 7.73(3), indicating that this compound will exist as a zwitterion in the environment(SRC).

The pKas of 3.23 (carboxylic acid) and 7.73 (cyclic primary amine)(1) indicate kasugamycin will exist as a zwitterion at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. Kasugamycin is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.3X10-4 mm(2).

Occupational exposure and general population exposure should be low or non-existent since kasugamycin is not produced or used in the US(SRC). Tolerance guidelines indicate that the general population may be exposed to kasugamycin via ingestion of certain imported foods(1).

Kasugamycin ... is active against Pseudomonas, Erwinia, Xanthomonas and Corynebacterium bacterial species.|Based on the remarkable low toxicity of kasugamycin, it was tested and proven to be effective against Pseudomonas aeruginosa urinary infections in humans.

When a rabbit was sc injected with ... /100 mg/kg/ of kasugamycin, the fungicide disappeared from the blood within 8 hr, and 96% of the injected material was excreted into urine in 8 hr after injection; kasugamycin concn in the urine was highest (43 mg/mL) after 45 min.|Oral admin of 100 mg/kg kasugamycin to mice indicated rapid absorption and 43 to 68% excretion with urine in 6 hr.|On im injection of 1.0g kasugamycin into humans, about 63% of the fungicide was excreted unchanged with urine in 8 hr.|In the rat metabolism study, the mean radioactivity recovery 168 hours after exposure ranged from 91 to 97%, with the majority of the dose recovered within 48 hours in the feces (81.9-93.9%) and urine (1.26-3.07%). The maximum concentration found in the plasma of both males and females occurred approximately one hour after the administration of a single low or high dose. Between one and six hours after a single low or high dose, more kasugamycin accumulated in the kidneys, urinary bladder, and lymph nodes than in the blood, but after 168 hours, little or no kasugamycin was found in these tissues. The absorption and metabolism of kasugamycin in rats was limited (less than 5% of the dose) and was not affected by sex, dose level, or duration of dosing. The parent compound was the major component identified in the urine, feces, liver, kidney, and plasma. Minor amounts (less than 1% of the dose) of the metabolite kasuganobiosamine were identified in urine, liver, kidney, and plasma, but none was detected in the feces. Elimination occurred primarily in the feces (88 to 95%), suggesting low absorption; kasugamycin was not excreted in the bile (enterohepatic circulation did not occur).

In the tomato metabolism study, the metabolite profile was similar for tomato fruit and foliage. ... The major metabolic pathway of kasugamycin in plants involves conjugation of the parent compound, conversion to kasugamycinic acid, and subsequent conjugation of kasugamycinic acid. Conversion of kasugamycin to 2-N-acetyl kasugamycin and kasuganobiosamine was thought to be a minor metabolic route. Parent compound (kasugamycin per se) was the major identified component in all samples from all harvest intervals.|In the rat metabolism study, the mean radioactivity recovery 168 hours after exposure ranged from 91 to 97%, with the majority of the dose recovered within 48 hours in the feces (81.9-93.9%) and urine (1.26-3.07%). ... The absorption and metabolism of kasugamycin in rats was limited (less than 5% of the dose) and was not affected by sex, dose level, or duration of dosing. The parent compound was the major component identified in the urine, feces, liver, kidney, and plasma. Minor amounts (less than 1% of the dose) of the metabolite kasuganobiosamine were identified in urine, liver, kidney, and plasma, but none was detected in the feces.

In cell-free systems, kasugamycin inhibited protein synthesis in Pyricularia oryzae and Pseudomonas fluorescens markedly but much less so in rat liver preparation. The antibiotic was shown to interfere with aminoacyl-tRNA binding to the 30-S ribosomal subunit of Escherichia coli ... Kasugamycin is inhibitory to P. oryzae in acidic (pH = 5) but not in neutral media.|... Kasugamycin affects translational accuracy in vitro. The drug decreases the incorporation of histidine relative to alanine into the coat protein of phage MS2, the gene of which is devoid of histidine codons. The read-through of the MS2 coat cistron is suppressed by the antibiotic. ... The effects of kasugamycin take place at concentrations that do not inhibit coat protein biosynthesis. Kasugamycin-resistant mutants (ksgA) lacking dimethylation of two adjacent adenosines in 16 S ribosomal RNA, show an increased leakiness of nonsense and frameshift mutants (in the absence of antibiotic).

Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

3-O-(2-amino-4((carboxyiminomethyl)amino)-2,3,4,6-tetradeoxy-alpha-D-arabino-hexopyranosyl)-D-chiroinositol

Trade names: Kasu, Kasumin, Kiasu|Dust, liquid, ULV, wettable powder.|Kasugamycin is usually sold as hydrochloride hydrate. Typical formulations for spraying, dusting, or seed treatment are wettable powders and soluble liquid concn alone (0.3 to 3% active ingredient) or in combination with other pesticides.

Kasugamycin HCl hydrate is more stable than the free base and does not deteriorate upon storage at 50 °C for 10 days. It tolerates weak acids, decomposes slowly at a pH of 7, and decomposes faster within weeks in alkaline soln at ambient temp.|Kasugamycin ... is an aminoglycoside antibiotic produced by Streptomyces kasugaenesis.|... Has largely been replaced by more modern compounds but remains important in some countries because of its low price.|Not registered, import tolerance established|Kasugamycin is not registered in the U.S., however, tolerances were established to cover residues on imported tomatoes and peppers from Mexico where the registrant is seeking to register Kasumin 2L, a liquid formulation comprised of 2% kasugamycin (by weight) as the active ingredient (ai), for use on rice, potato, pepper, and tomato in Mexico.

Product analysis by cup assay with Pseudomonas fluorescens (NIHJ B-254). Residues determined by cup assay with Pyricularia oryzae (P2)

Agrochemicals -> Bactericides, Fungicides