3-メチルチオ-2-ブタノンO-(メチルカルバモイル)オキシム

Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Carbamate Insecticides

Pesticide (Butocarboxim) -> USDA PDB

log Kow = 1.1

1.11

Soluble in most organic solvents.

Completely miscible with aromatic hydrocarbons, esters, and ketones. Low solubility in aliphatic hydrocarbons (11 g/l) and carbon tetrachloride.

In water, 35 g/l @ 20 °C

0.0000795 [mmHg]

7.95X10-5 mm Hg @ 20 °C

Pale brown liquid (technical product); (E)- isomer: mp = 37 deg C; (Z)- isomer: liquid at room temperature; [HSDB] Nearly colorless liquid (partially crystallized); mp = 34-37 deg C; [INCHEM JMPR] Colorless solid; mp = 32-37 deg C; [MSDSonline]

Liquid /Technical/

stable at pH 4-7

Danger

H226: Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P321, P330, P337+P317, P361+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Danger

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P321, P330, P337+P317, P361+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

A mild skin and moderate eye irritant; No effects observed on fertility, growth rate, or mortality and no evidence of carcinogenicity or mutagenicity in two year feeding study with rats at highest dose (300 mg/kg diet); [HSDB] An eye irritant; [eChemPortal: ESIS] See CARBAMATE INSECTICIDES.

Flam. Liq. 3 (100%)

Flammable liquid - category 3

Flam. Liq. 3

Slightly irritating to skin, moderately irritating to eyes.

Carbamates produce slight to moderate skin and eye irritation, depending on the vehicle used, duration of contact, and on whether the substance is applied to the abraided or intact skin. From the available data, it cannot be excluded that some of the carbamates will have a slight to moderate sensitization potential. /Carbamate Pesticides/

Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baseline; Butylcholinesterase activity in serum or plasma = 60% of individual's baseline; Sample at end of shift; [TLVs and BEIs]

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.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

The protective clothing should be kept in separate places where it cannot be contaminated with toxic chemicals. It should be forbidden to keep this clothing in living quarters. Protective clothing must be washed at least once a week and each time it is contaminated with pesticides. Before washing the clothing should be soaked for several hours in a calcium carbonate solution. /Pesticides/

Smoking, eating, and drinking before washing should be absolutely prohibited when any pesticide ... is being handled or used. /Pesticides/

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (A15321).

LC50 Rainbow trout 38 mg/l (24 hr) /Conditions of bioassay not specified/

LD50 Mallard duck 64 mg/kg

LC50 Japanese quail 1,180 mg/kg diet/8 days

LC50 Rainbow trout 29 mg/l/96 hr /Conditions of bioassay not specified/

For more Ecotoxicity Values (Complete) data for BUTOCARBOXIM (8 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 37(SRC), determined from a structure estimation method(2), indicates that butocarboxim is expected to have very high mobility in soil(SRC). Volatilization of butocarboxim from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 5.70X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 7.95X10-5 mm Hg(3) and water solubility, 35,000 mg/l(3). Butocarboxim is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Half-lives in soils were reported as 1-8 days(3). Butocarboxim was found to degrade on sterilized soils exposed to sunlight; half-lives were approximately 9-11 days(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 37(SRC), determined from a structure estimation method(2), indicates that butocarboxim is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 5.70X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 7.95X10-5 mm Hg(4) and water solubility, 35,000 mg/l(4). According to a classification scheme(5), an estimated BCF of 1.4(SRC), from its log Kow of 1.1(4) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low. Butocarboxim is stable at pH 5-7, up to 50 °C, but is hydrolyzed by strong acids and alkalis(4).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), butocarboxim, which has a vapor pressure of 7.95X10-5 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase butocarboxim 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 15 hours(SRC), calculated from its rate constant of 2.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase butocarboxim may be removed from the air by wet and dry deposition(SRC). Butocarboxim was found to photodegrade on sterilized soil surfaces when exposed to sunlight(4), but no data were found regarding direct photolysis in air by sunlight(SRC).

Butocarboxim is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop.

/BIRDS and MAMMALS/ As a rule, birds are not very sensitive to carbamates. /Carbamate pesticides/

/BIRDS and MAMMALS/ Day-old chicks were fed on ration containing 500, 1,000, and 1,500 ppm of butocarboxim for 75 consecutive days. Blood analysis at fortnightiy intervals revealed dose dependent and progressive reduction in blood cholinesterase activity of the birds. The insecticide fed birds also showed significant elevation in serum glutamic pyruvate transaminase and urea nitrogen levels.

/AQUATIC SPECIES/ Although carbamates are not very stable under aquatic conditions, and will not persist long in this environment, some carbamates are highly toxic for invertebrates and fish, others /are/ much less /toxic/. Some /carbamates/ bioaccumulate in fish, mainly because the metabolism is slow in /these animals/. /Carbamate Pesticides/

/OTHER TERRESTRIAL SPECIES/ Toxic to bees.

/OTHER TERRESTRIAL SPECIES/ In laboratory tests the active ingredient of Co 755 proved harmless to predators such as lady bugs. The preliminary LD5O per os for bees lies at approximately 1 mug/animal.

As with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (L795)

SRP: Workers should undergo an annual medical exam. Contraindications for work with organophosporous pesticides are organic diseases of the CNS, mental disorders and epilepsy, and pronounced endocrine disorders. Blood cholinesterase, both plasma and RBC, must be determined before work starts. In the event of prolonged work periods, this activity should be determined at intervals of 3-4 days. Persons exhibiting a fall in cholinesterase activity of 25% or more must be transferred to other work where they are not exposed until cholinesterase activity is restored. /Organophosphorous pesticides; Anticholinesterase pesticides/

Measurement of whole blood-AChE is the most widely adopted method for monitoring the effects of occupational exposure to organophosphorus insecticides. Physiological variations in blood ChE levels occur in a healthy person and are seen among a population. It has been estimated that the coefficient of variation for AChE activity in samples from an individual is 8-11%, and that a decrease of 23% below pre-exposure level may, therefore, be considered significant. If the average of several pre-exposure values were available, then a decrease of 17% would be significant. It has been recommended that, if measured activity is reduced by 30% or more of the pre-exposure value, AChE measurements should be repeated at appropriate intervals to confirm the results. Depressions of AChE or ChE in excess of 20-25% are considered diagnostic of exposure but not, necessarily, indicative of hazard. Depressions of 30-50% or more are considered indicators for removal of an exposed individual from further contact with pesticides until levels return to normal. /Organophosphorus pesticides; Anticholinesterase pesticides/

...Organophosphorus pesticides may undergo hydrolysis in vivo to yield substituted phosphoric acids that are subsequently excreted in urine. Advances in gas chromatography and combined gas chromatography/mass spectrometry (GC/MS) have made it possible to analyse the urine of exposed persons for the presence of appropriate metabolites. It is usually necessary to preserve the sample by the addition of chloroform, to concentrate or extract the metabolite(s), and to convert them to suitably-volatile derivatives that can be detected by GC. Obviously, access to a well-equipped analytical laboratory, capable of the quick processing of samples, is a necessary factor if monitoring by urine analysis is proposed. However, in some cases, simpler and sensitive colorimetric tests are available for screening the urine of exposed persons. Thus, 4-nitrophenol can be measured directly in the urine of workers exposed to parathion. Consideration of the concentration of metabolite(s) in the urine can be helpful in determining patterns of exposure, and these concentrations can be calibrated against the effects on AChE for a particular pesticide. However, the time-course and peak of excretion of metabolites appears to vary according to dose, so that serial sampling and analyses of urine are desirable. Levels of metabolite alone cannot be considered a guide to hazard. This is obvious when it is realized that pesticides that have very different toxicities may yield identical acidic metabolites. Thus, the level of metabolites in urine, after exposure to sufficient amounts of the very toxic parathion-methyl to depress blood-AChE to 50%, will be much lower than that of the identical metabolites, following exposure to the related fenitrothion, which is about 40 times less toxic. /Organophosphorus pesticides; Anticholinesterase pesticides/

Using a structure estimation method based on molecular connectivity indices(1), the Koc for butocarboxim can be estimated to be 37(SRC). According to a classification scheme(2), this estimated Koc value suggests that butocarboxim is expected to have very high mobility in soil.

/SIGNS AND SYMPTOMS/ The clinical picture of carbamates intoxication results from accumulation of ACh at nerve endings. ...The signs and symptoms can be categorized into the following 3 groups: (a) Muscarinic manifestations - increased bronchial secretion, excessive sweating, salivation, and lachrymation; pinpoint pupils, bronchoconstriction, abdominal cramps (vomiting and diarrhea); and bradycardia. (b) Nicotinic manifestations - fasciculation of fine muscles (in severe cases, diaphragm and respiratory muscles also involved); and tachycardia. (c) Central nervous system manifestations- headache, dizziness, anxiety, mental confusion, convulsions, and coma; and depression of respiratory center. All these signs and symptoms can occur in different combinations and can vary in onset and sequence, depending on the chemical, dose, and route of exposure. The duration of symptoms is usually shorter than that observed in organophosphorus poisoning. Mild poisoning might include muscarinic and nicotinic signs only. Severe cases always show central nervous system involvement; the clinical picture is dominated by the respiratory failure sometimes leading to pulmonary edema due to the combination of the above mentioned symptoms. /Carbamate pesticides/

/SIGNS AND SYMPTOMS/ Principal effects /of anticholinesterases as toxic components of insecticides/ on eye, whether from local contact or systemic poisoning, are miosis and spasm of accommodation for near vision. /Anticholinesterases/

Carbamates are effective insecticides by virtue of their ability to inhibit acetylcholinesterase (AChE) in the nervous system. They also inhibit other esterases. The carbamylation of the enzyme is unstable, and the regeneration of AChE is relatively rapid compared with that from a phosphorylated enzyme. /Carbamate Pesticides/

In mammals, following oral administration, metabolised to butoxycarboxim, and excreted in the urine as butoxycarboxim and its...products.

The first step in the metabolism of carbamates is hydrolysis to carbamic acid, which decomposes to carbon dioxide (CO2) and the corresponding amine. The mechanism of hydrolysis is different for N -methyl and N -dimethyl derivatives. The N -methyl carbamates pass through an isocyanate intermediate, whereas in the hydrolysis of N - dimethylcarbamates, an addition product with a hydroxyl ion is formed yielding the alcohol and N -dimethyl substituted acid. The rate of hydrolysis by esterases is faster in mammals than in plants and insects. Apart from hydrolysis, oxidation also takes place including: hydroxylation of the aromatic ring, O -dealkylation, N -methyl hydroxylation, N -dealkylation, oxidation of aliphatic side chains, and sulfoxidation to the corresponding sulfone. Oxidation is associated with the mixed-function oxidase (MFO) enzymes. Conjugation leads to the formation of O - and N -glucuronides, sulfates, and mercapturic acid derivatives in mammals. Glycosides and phosphates are conjugation products more common in plants. /Carbamate Pesticides/

The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)

Little information is available on the distribution of carbamates in the various organs and tissues in mammals following exposure by inhalation or the oral route. The organs in which residues have been reported are the liver, kidneys, brain, fat, and muscle. The half-life in the rat is of the order of 3-8 hr. ...It seems that the excretion of carbamates via urine is also rapid in man, and that the metabolic pathways in man are the same as those in the rat. /Carbamate Pesticides/

Used as systemic insecticide for sucking insects in citrus, cotton, vegetables, fruit trees, and ornamentals; [HSDB] Also provides good secondary control of mites; Used in some European countries, Israel, and Taiwan (as of 1983); [INCHEM JMPR]

Cancelled--no longer registered as a pesticide for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

Systemic insecticide. For sucking insects, especially Aleurotrixus floccosus in citrus; Bemisia tabaci in cotton; aphids in vegetables, fruit trees; ornamentals in hydroculture.

...Recommended use rates range from 0.3-3.5 kg/ha on most commodities, with post-treatment intervals varying from 3-21 days. There are no post-harvest, animal or soil treatment uses, but ornamental uses include soil drenching and hydroponic incorporation.

Status: Cancelled

Emulsifiable concentrates.

Obtained as a 85% tech concentrate in xylene containing (E)- and (Z)-isomers in a ratio of 85-90:15-10 /Technical/

Aerosol dispenser, emulsifiable concentrate, soluble concentrate.

Tradenames: 'Drawin' (Wacker); 'Systemschutz D' (Wacker); 'Hydrosekt' (Luxan)

...It is marketed as either a 25% or 50% ai emulsifiable concentrate, which is diluted to 0.1-0.15% with water for spray application.

The WHO Recommended Classification of Pesticides by Hazard identifies Butocarboxim (technical grade) as Class IB: highly hazardous; Main Use: insecticide.

Butocarboxim is a systemic insecticide of the oximcarbamate family