(6R,25R)-5-O-Demethyl-28-deoxy-6,28-epoxy-25-methylmilbemycin B
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(6R,25R)-5-O-Demethyl-28-deoxy-6,28-epoxy-25-methylmilbemycin B
structure -
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CAS No:
51596-10-2
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Formula:
C31H44O7
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Chemical Name:
(6R,25R)-5-O-Demethyl-28-deoxy-6,28-epoxy-25-methylmilbemycin B
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Synonyms:
Milbemycin B,5-O-demethyl-28-deoxy-6,28-epoxy-25-methyl-,(6R,25R)-;Spiro[11,15-methano-2H,7H,13H-furo[4,3,2-pq][2,6]benzodioxacyclooctadecin-13,2′-[2H]pyran],milbemycin B deriv.;(6R,25R)-5-O-Demethyl-28-deoxy-6,28-epoxy-25-methylmilbemycin B;Antibiotic B 41A3;Milbemycin α1;Milbemycin A3;(+)-Milbemycin α1;Milbeknock;GWN 1725;Gowan 1725;Matsuguard;Koromite;Mesa;Emamectin A3;Mesa (acaricide);Ultiflora;Milbemectin;56197-00-3
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CAS No:
(6R,25R)-5-O-Demethyl-28-deoxy-6,28-epoxy-25-methylmilbemycin B Basic Attributes
528.67700
528.68
610-705-0
C76Y8Z9GEX
DTXSID1058391
White, crystalline powder (Technical grade)
Characteristics
94.45000
4.53420
1.21g/cm3
213.5 °C
725.5ºC at 760mmHg
233.1ºC
1.577
1.66e-06 M|Milbemycin A3: In methanol 64.8, ethanol 41.9, acetone 66.1, n-hexane 1.4, benzene 143.1, ethyl acetate 69.5 (all in g/L, 20 °C). Milbemycin A4: In methanol 458.8, ethanol 234.0, acetone 365.3, n-hexane 6.5, benzene 524.2, ethyl acetate 320.4 (all in g/L, 20 °C).|Milbemycin A3: In water 0.88 ppm (20 °C). Milbemycin A4: In water 7.2 ppm (20 °C)
0-6ºC
9.8X10-11 mm Hg at 20 °C
Henry's Law constant = 3.8X10-15 atm-cu m/mole at 25 °C (est)
Hydroxyl radical reaction rate constant = 4.7X10-10 cu cm/molecule-sec at 25 °C (est)
Safety Information
III
6.1(b)
UN 2588
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.|Do not contaminate water, foodstuff or feed by disposal. Open dumping or burning of this product or its packaging is prohibited. Burning in an incinerator can be made in accordance with local relevant laws and regulations. However, the appropriate regulatory agencies should be contacted prior to disposal, because acceptable methods of disposal may vary by location, and regulatory requirements may change. ... /Ultiflora Miticide/|This product is toxic to fish ... Drift or runoff from treated area may be hazardous to aquatic organisms in neighboring aquatic site. Do not contaminate water when disposing of equipment washwaters. /Ultiflora Miticide/|... Pesticide Disposal: Wastes resulting from the use of this product may be disposed of ... at an approved waste disposal facility. ... /Ultiflora Miticide/|... Container Disposal: Triple rinse (or equivalent). Then offer for recycling or reconditioning, or puncture and dispose of in a sanitary landfill, or incineration or, if allowed by state and local authorities, by burning. If burned, stay out of smoke. /Ultiflora Miticide/
European Commission/Health & Consumer protection Directorate-General; Commission Working Document on Milbemectin (04 April 2005). Available from: http://ec.europa.eu/food/plant/protection/evaluation/newactive/milbemectin_draft_review_report.pdf as of February 21, 2008.|California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summaries. Available from: http://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.htm on Milbemectin as of February 7, 2008.
Personal protective equipment (PPE): Some materials that are chemical-resistant to this product are listed below. If you want more options, follow the instructions for category F on an EPA chemical resistance category selection chart. Mixers, loaders, applicators and other handlers must wear: Long-sleeved shirt and long pants; Chemical-resistant gloves, such as barrier laminate, butyl or nitrile rubber or Viton; Shoes plus socks. Follow manufacturer's instructions for cleaning/maintaining PPE. If no such instructions for washables, use detergent and hot water. Keep and wash PPE separately from other laundry. /Ultiflora Miticide/
Ultiflora is a flammable liquid. Major flammable constituents are cyclohexanone and aromatic hydrocarbons. /Ultiflora Miticide/
Appropriate Extinguishing Media: CO2, dry chemical, foam, water. Fire Fighting Guidance: Move containers from fire area if it can be done without risk. Isolate hazard area; avoid inhalation of smoke and fumes. Contain runoff by diking to prevent entry into sewers or waterways. /Ultiflora Miticide/
Keep material out of streams and sewers. Dike to confine spill and absorb with an absorbent such as clay, sand or soil. Vacuum, shovel or pump wastes into a drum for later disposal. Wash area with water and detergent thoroughly and collect washwaters into a drum for later disposal. /Ultiflora Miticide/
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
Toxicity
LD50 Rat oral 456 mg/kg /From table/|LD50 Rat (male) oral 5200 mg/kg /Ultiflora Miticide/|LD50 Rat (female) oral 5300 mg/kg /Ultiflora Miticide/|LD50 Rat dermal >5000 mg/kg /From table/|For more Non-Human Toxicity Values (Complete) data for MILBEMECTIN (6 total), please visit the HSDB record page.
/OTHER TERRESTRIAL SPECIES/ Apis mellifera (honeybee) cage study with Milbeknock 1% EC - endpoints: mortality, foraging, brood - dosages: 27.9 active substance (as)/hectare (ha) (exposure to dried residues), 2.96 g as/ha (direct spray) and 7.5 g as/ha (direct spray) - effects: no effects at the three tested dosages. /Milbeknock 1% EC/ /From table/
Milbenectin is a mixture of natural compounds (milbemycins) is derived from the soil microorganism Streptomyces hygroscopias subsp aureolacrimosus.
Milbemectin's production may result in its release to the environment through various waste streams; its use as an acaricide and insecticide(1) will result in its direct release to the environment(SRC). Milbemectin is a mixture of homologues milbemycin A3 (methyl) and milbemycin A4 (ethyl) in the ratio 3 to 7(1).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 38,600(SRC), determined from a log Kow of 5.9(2) and a regression-derived equation(3), indicates that milbemectin is expected to be immobile in soil(SRC). Volatilization of milbemectin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.8X10-15 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Milbemectin is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.8X10-11 mm Hg at 20 °C(5). The half-life of milbemectin in soil was reported to range from 16 to 33 days(2).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 38,600(SRC), determined from a log Kow of 5.9(2) and a regression-derived equation(3), indicates that milbemectin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.8X10-15 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 7000(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). Biodegradation data for milbemectin in water were not located(SRC, 2008); however, a biodegradation half-life of 16-33 days in soil(2) suggests biodegradation in natural water may be an important environmental fate process(SRC). Milbemectin is reported to hydrolyze in alkaline media(2); however, no rate for this reaction was reported.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), milbemectin, which has a vapor pressure of 9.8X10-11 mm Hg at 20 °C(2), is expected to exist solely in the particulate phase. Particulate-phase milbemectin may be removed from the air by wet or dry deposition(SRC). Milbemectin contains chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight(3).
Milbemectin was reported as unstable in alkaline media(1) and is expected to undergo hydrolysis in the environment since it contains functional groups that hydrolyze under environmental conditions(2); however, the rate of this reaction is not known(SRC). Milbemectin contains chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight(2).
An estimated BCF of 7,000 was calculated in fish for milbemectin(SRC), using a log Kow of 5.9(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC), provided the compound is not metabolized by the organism(SRC).
The Koc of milbemectin is estimated as 38,600(SRC), using a log Kow of 5.9(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that milbemectin is expected to be immobile in soil(SRC).
The Henry's Law constant for milbemectin is estimated as 3.8X10-15 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that milbemectin is expected to be essentially nonvolatile from water surfaces(2). Milbemectin's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to be an important environmental fate process(SRC). Milbemectin is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.8X10-11 mm Hg at 20 °C(3).
Occupational exposure may occur through dermal contact with this compound at workplaces where it is produced or used. (SRC)
Drug Information
Agents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal. (See all compounds classified as Anthelmintics.)|Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice. (See all compounds classified as Antinematodal Agents.)|Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)
Absorption, distribution, excretion and metabolism in mammals: At least 47% /absorbed/ at single low dose (2.5 mg/kg), based on biliary and urinary excretion. Widely distributed; highest residues in adrenals, kidneys, pancreas, lymph nodes, and reproductive fat. No evidence for accumulation. /24 hr excretion/ urinary 5 to 9%; fecal 85 to 100%. /From table/|Fischer 344 rats (5/sex/group) were dosed with (14)C-Milbemycin A4 (14C-E187) orally by gavage at dose levels of 2.5 mg/kg (low dose) and 25 mg/kg (high dose) according to the following regimen: (1) single low dose; (2) 14-day repeated nonlabelled dose followed by a single carbon-14 low dose; (3) single high dose; (4) single low dose to monitor pharmacokinetics; and (5) single high dose for pharmacokinetics. Tissue distribution studies were conducted using 9 rats/sex/group by administering single oral low and high doses. Bile cannulation studies were conducted using 4 rats/sex/group by admin single oral low and high doses. For the single oral low and high dose and repeated dose groups, the mean total recoveries of the admin (14)C ranged from 93.7 to 106%, with 81.5 to 100% eliminated in feces and 3.28 to 9.29% in urine. The amt in the remaining tissues were < 0.44% of the total radioactive residue (TRR). Excretion of carbon-14 was rapid with most being excreted within 24 hr of admin. The amt of carbon-14 detected in bile and urine indicated that ca 50% (at low dose) and 30% (at high dose) of carbon-14 was absorbed. Following the oral dose, the plasma concn of carbon-14 peaked after 2 to 3 hr post-dose. Most of the carbon-14 in tissues was found in the gastrointestinal tract or in the liver ...
Extensively metabolised /in animals/ (no parent compound in faeces or bile at low dose) mainly by hydroxylation, also evidence for minor glucuronidation pathway. /From table/|Fifty-three Fischer 344 rats (5/sex/group) were dosed with (14)C-Milbemycin A4 ((14)C-E187) orally by gavage ... The major metabolite found in plasma, liver, and kidney samples was 13-hydroxy A4, accounting for up to 60.2, 52.4, and 66.7% of the total radioactive residue, respectively. The following metabolites were characterized from the feces: dihydroxylated A4s (3 metabolites); and trihydroxylated A4s (2 metabolites). The major urinary metabolite was dihydroxylated A4s (0.95 to 4.38% of admin dose).
... Milbeknock acts on the nervous system mediated with inhibitory neurotransmitter, GABA (g-Amino butyric acid). /Milbeknock/
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ 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/|/SRP:/ 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/
5-hydroxymilbemycin beta7
(6R,25R)-5-O-Demethyl-28-deoxy-6,28-epoxy-25-methylmilbemycin B Use and Manufacturing
Milbemectin is a mixture of natural compounds derived from fermentation of the soil microorganism Streptomyces hygroscopicus subsp. aureolacrimosus
Trade name: Milbeknock (milbemectin 1% EC)|Trade name: Ultiflora/Ultiflora Miticide (Milbemectin (1 % w/w))|Milbemectin is formulated as an emulsifiable concentrate (EC) or wettable powder (WP)
Milbemectin is a mixture of homologues milbemycin A3 (methyl) and milbemycin A4 (ethyl) in the ratio 3 to 7
Agrochemicals -> Insecticides|Nematicides, Acaricides, Insecticides
Computed Properties
Molecular Weight:528.7
XLogP3:3.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:7
Exact Mass:528.30870374
Monoisotopic Mass:528.30870374
Topological Polar Surface Area:94.4
Heavy Atom Count:38
Complexity:1040
Defined Atom Stereocenter Count:10
Defined Bond Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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