Amitraz
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Amitraz
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CAS No:
33089-61-1
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Formula:
C19H23N3
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Chemical Name:
Amitraz
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Synonyms:
Methanimidamide,N′-(2,4-dimethylphenyl)-N-[[(2,4-dimethylphenyl)imino]methyl]-N-methyl-;Formamidine,N-methyl-N′-2,4-xylyl-N-(N-2,4-xylylformimidoyl)-;N′-(2,4-Dimethylphenyl)-N-[[(2,4-dimethylphenyl)imino]methyl]-N-methylmethanimidamide;U 36059;BTS 27419;Azaform;Amitraz;Triazid;BAAM;1,5-Di(2,4-dimethylphenyl)-3-methyl-1,3,5-triazapenta-1,4-diene;Taktic;Edrizar;Mitac;Fumilat A;Mitaban;BAAM (pesticide);TCL;Varamit;Ovasyn;Bovitraz;Ektodex;Acarac;ENT 27967;NSC 324552;Parsec;Amigard;N′-(2,4-Dimethylphenyl)-N-[(2,4-dimethylphenyl)imino]methyl-N-methylimidoformamide;Apivar ND;ApiVar;Preventic;Triatox;51847-94-0
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CAS No:
Description
Amitraz is a non-systemic acaricide and insecticide, with alpha-adrenergic agonist activity, interaction with octopamine receptors of the central nervous system and inhibition of monoamine oxidases and prostaglandin synthesis.
Amitraz appears as white monoclinic crystals. Melting point 187-189°F (86-87°C). Insoluble in water. Used as an acaricide, insecticide and treatment of demodectic mange in dogs.|COLOURLESS CRYSTALS.
Amitraz appears as white monoclinic crystals. Melting point 187-189°F (86-87°C). Insoluble in water. Used as an acaricide, insecticide and treatment of demodectic mange in dogs.|Amitraz is a tertiary amino compound that is 1,3,5-triazapenta-1,4-diene substituted by a methyl group at position 3 and 2,4-dimethylphenyl groups at positions 1 and 5. It has a role as an acaricide, a xenobiotic, an environmental contaminant and an insecticide. It is a tertiary amino compound and a member of formamidines.|Amitraz is a non-systemic acaricide and insecticide. It was generated in 1969 by the Boots Co. in England. Amitraz presents insect repellent effects and hence, it can be used as an insecticide and pesticide. Its insecticide effect is due to its agonistic activity in the alpha-adrenergic system, its interaction with the octopamine receptors in the central nervous system and its driven inhibition of the synthesis of monoamine oxidases and prostaglandins. All the abovementioned effects are translated into the overexcitation, paralysis, and death in insects. Amitraz presents a lower effect in mammals and thus, it is widely used in the treatment of mite- or tick-infestation of dogs.
Amitraz Basic Attributes
293.41
293.41
251-375-4
33IAH5017S
0098
758952|324552
2588
DTXSID5023871
White/pale yellow crystalline solid|Colorless needles|White monoclinic needles
QP53AX65|QP53AD51
2925290030
Characteristics
28
5.50
White Powder/Solid
1.1 g/cm3
86-87 °C
450.7±55.0 °C at 760 mmHg
226.4±31.5 °C
1.546
Solubility in water: none
0-6°C
Vapour pressure, Pa at 20°C: (negligible)
Oral-Rat LD50: 400 mg/kg; Oral-Mouse LD50:1600 mg/kg
Combustion produces toxic nitrogen oxide gas
Slight amine odor
9.87e-06 atm-m3/mole|Henry's Law constant = 9.87X10-6 atm-cu m/mol at 25 °C
pKa = 4.20
Unstable to acidic pH|Hydroxyl radical reaction rate constant = 1.33X10-10 cu cm/molec-sec at 25 °C (est)
Insoluble in water.
Amines, Phosphines, and Pyridines
Unstable in acid.
Safety Information
9
UN 3077
3
22-43-48/22-50/53
22-24-36/37-60-61
ZF0480000
Xn;N,N,Xn
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
Amitraz is unstable under acidic conditions.
P260-P280-P301 + P312 + P330
H302-H317-H373-H410
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.|Do not reuse empty pouch or box. Wrap pouch and put in trash collection. When discarding cut off end and used collar, wrap in newspaper and place in trash collection. Dispose of in accordance with all applicable federal, state, and local laws. /Prevent Tick Collar for Dogs/|Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal. /Residential users/|Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Many communities have programs to recycle household waste such as empty bottles and cans. Do not recycle any pesticide containers, however, unless the recycling program specifically accepts pesticide containers and you follow the program's instructions for preparing the empty containers for collection. /Residential users/
Amitraz is unstable under acidic conditions.
Amitraz liquid. ... For dogs for the treatment of generalized demodicosis ( Demodex canis ). ... Federal law restricts this drug to use by or on the order of a licensed veterinarian.|The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Amitraz is included on this list.
USEPA/Office of Pesticide Programs; Report of the Food Quality Protection Act (FQPA) Tolerance Reassessment Progress and Risk Management Decision (TRED) for Amitraz. EPA issues a TRED for a pesticide that requires tolerance reassessment decisions, but does not require a reregistration eligibility decision at present because: the pesticide was initially registered after November 1, 1984, and by law is not included within the scope of the reregistration program; EPA completed a RED for the pesticide before FQPA was enacted on August 3, 1996; or the pesticide is not registered for use in the U.S. but tolerances are established that allow crops treated with the pesticide to be imported from other countries.[Available from, as of August 23, 2012: http://www.epa.gov/pesticides/reregistration/status.htm]|USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Amitraz (March 1995). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of January 26, 2012: http://www.epa.gov/pesticides/reregistration/status.htm]
Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire. Risk of fire and explosion if formulations contain flammable/explosive solvents.
|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P314, P321, P330, P333+P313, P363, P391, and P501|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P312, P314, P321, P322, P330, P333+P313, P361, P363, P391, P405, and P501|Aggregated GHS information provided by 266 companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P260, P261, P264, P270, P272, P280, P301+P312, P302+P352, P309+P311, P314, P321, P330, P333+P313, P363, P405, and P501|P201, P202, P260, P261, P264, P270, P271, P272, P273, P280, P281, P301+P312, P302+P352, P304+P340, P307+P311, P308+P313, P312, P314, P321, P330, P333+P313, P363, P391, P403+P233, P405, and P501
Wear protective gloves and clothing to prevent any reasonable probability of skin contact. ... All protective clothing (suits, gloves, footwear, headgear) should be clean, available each day, and put on before work. ... wear dust-proof chemical goggles and face shield unless full facepiece respriatory protection is worn. ...|Rubber gloves for prolonged or repeated exposure. /Prevent Tick Collar for Dogs/
Fire Extinguishing Media: Water, foam, dry powder, CO2.|Firefighters should wear self-contained breathing apparatus and full protective equipment in fire situations. /Prevent Tick Collar for Dogs/
If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label./Residential users/|After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash. /Residential users/
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. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.|SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.|Avoid prolonged or repeated contact with this product. Wash hands thoroughly with soap and water after handling and before eating, drinking, chewing gum or using tobacco. /Prevent Tick Collar for Dogs/|... Employees should wash immediately with soap when skin is wet or contaminated. ...|For more Preventive Measures (Complete) data for AMITRAZ (9 total), please visit the HSDB record page.
... Eye or skin contact can cause irritation. ...
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access.
No indication can be given about the rate at which a harmful concentration of this substance in the air is reached.
The substance may cause effects on the central nervous system and cardiovascular system.
NO open flames.
STRICT HYGIENE! AVOID EXPOSURE OF BREASTFEEDING WOMEN! AVOID EXPOSURE OF ADOLESCENTS AND CHILDREN!
Use ventilation (not if powder).
Protective gloves. Protective clothing.
Wear safety spectacles or face shield.
Amitraz was not detected in fifteen animal feed concentrate samples from Karnal (Haryana) India(1).
Toxicity
moderately
Three different insecticides: dimethoate, cypermethrin and amitraz were given, alone or combined with the heavy metals Pb, Hg and Cd, to male Wistar rats ... /by oral administration/ for 12 weeks from their 4th week of life. After the treatment period, the left hemisphere of the rats was exposed in urethane anesthesia, and spontaneous and evoked cortical activity was recorded from the primary sensory areas. The effects of dimethoate on the spontaneous activity, and of dimethoate and amitraz on the evoked responses, were increased by the metal combination treatment, whereby the metals alone had no effect on the spontaneous and mild effect on the evoked activity. Finally, the animals were dissected, organ weights measured, and relative organ weights calculated. The weight gain of all treated groups was significantly retarded compared to the control. Several organ weights were also significantly reduced, mainly in groups receiving insecticide plus metal treatment. The toxic interactions observed in this work indicate that combined human exposure to environmental pesticide residues and heavy metals may have unexpectedly severe effects.|Amitraz and thiram are pesticides that have been shown to disrupt luteinizing hormone (LH) secretion in rats, albeit by different mechanisms. Amitraz acts via alpha-noradrenergic antagonism; whereas thiram inhibits norepinephrine synthesis. Here, we sought to evaluate the cumulative effects of amitraz and thiram on pregnancy maintenance when administered during the LH-dependent period of pregnancy (days 7-10). To assess dose additivity, in Experiment 1, F344 rats were administered amitraz at 40 mg/kg (A40), thiram at 25 mg/kg (T25), or the two combined (AThigh) at 20 and 12.5 mg/kg, respectively, by gavage on gestation days (GD) 6-10. Controls received vehicle (1% methylcellulose). In Experiment 2, all doses were halved to yield treatments of A20, T12.5, and AT-low (A10 + T6.25). Tail-blood samples were taken from selected dams for assay of serum LH. Litters were examined on postnatal days (PD) 1 and 6. Full-litter resorption (FLR) was observed in 23 (79%), 8 (33%), and 18 (64%) of the dams in the A40, T25, and AT-high groups, respectively, and in 7 (41%), 3 (25%), and 1 (7%) of the dams in the A20, T12.5, and AT-low groups, respectively. One (5%) control dam had full-litter loss, but, unlike the other cases, the loss appeared to occur near term. Reduced serum LH levels were observed on GD 10 in A40, T25, and AT-high dams with FLR, and in A40 dams with live litters. For dams with surviving litters, delayed parturition was noted in the A40, T25, and AT-high groups. Surviving A40 litters had increased resorption rates and increased incidences of eye defects (microphthalmia, anophthalmia). Pup weights were reduced on PD 1 at A40 and T25. Thus, both chemicals, alone and in combination at the high doses, caused FLR and delayed parturition; these findings are consistent with dose additivity. Whereas the low doses of each chemical alone also caused FLR, dose additivity was not clearly demonstrated by the AT-low combination.
LD50 Rat oral 600 mg/kg bw|LD50 Rat oral 400 mg/kg|LD50 Rat ip 800 mg/kg|LD50 Mouse oral 1600 mg/kg|For more Non-Human Toxicity Values (Complete) data for AMITRAZ (12 total), please visit the HSDB record page.
/AQUATIC SPECIES/ Developmental effects of amitraz (acaricide), its metabolite (2,4-dimethylaniline), and paraquat (herbicide) on embryos of a nontarget organism, Xenopus laevis, were investigated. Following the standard protocol of the American Society for Testing and Materials (ASTM), the experiments were carried out using native Xenopus frogs. There was a drastic increase in mortality from 24 hr to 96 hr for paraquat, but 2,4-dimethylaniline showed no mortality at the highest concentration tested (100 mg/L). The 96-hr LC50 values were 0.67, 3.27, and >>100 mg/L for paraquat, amitraz, and 2,4-dimethylaniline, respectively. At concentrations higher than 0.2 mg/L of paraquat all the embryos were malformed, whereas growth reduction was apparent at all test concentrations (0.1-5 mg/L). The most common teratogenic effects were flexures of the notochord and stunting of growth. Edema was the most common effect of amitraz on the embryos, and 100% of the surviving embryos in 5 mg/L were edematous. The 96 hr EC50 (malformation) values were 1.21 (95% CI 0.48-3.03) and 0.18 (95% CI 0.16-0.20) mg/L for amitraz and paraquat, respectively. The ratio of 96 hr LC50 to 96 hr EC50 (malformation), i.e., the teratogenicity index (TI) were 2.7 and 3.72 for amitraz and paraquat, respectively, and for 2,4-dimethylaniline (TI > 5) all the embryos in 25 mg/L showed observable pigment loss and encephalomegaly. This shows that paraquat and the degradation product of amitraz, 2,4-dimethylaniline, should be classified as teratogens. Teratogenic risks of massive application of these pesticides on Kenyan farms should therefore be considered.|/OTHER TERRESTRIAL SPECIES/ Honey bee colonies were exposed to pesticides used in agriculture or within bee hives by beekeepers: coumaphos; diazinon; amitraz or fluvalinate. Samples of bee workers, larvae and royal jelly were analysed using Gas Chromatography-Electron Capture Detection (GC-ECD). Amitraz was quantified using High Performance Liquid Chromatography (HPLC). ... Amitraz residues in all sampled material were below the level of detection of 10 ng/g. ...|/FIELD STUDIES/ Toxic and genotoxic effects of alachlor, metolachlor, amitraz, chlordimeform, their respective environmentally stable degradation products 2,6-diethylaniline, 2-ethyl-4-methylaniline, 2,4-dimethylaniline, and two other related compounds, 3,4-dichloroaniline and aniline were compared. Acute toxicity tests with Chironomus riparius (96 hr) and Vibrio fischeri (Microtox) and genotoxicity tests with a dark mutant of V. fischeri (Mutato) were carried out. Our results demonstrate that toxicity and genotoxicity of the pesticides are retained upon degradation to their alkyl-aniline metabolites. In the case of the herbicides alachlor and metolachlor, the toxicity to V. fischeri was enhanced upon degradation. Narcosis alone explains toxicity of the compounds to the midge, but not so for the bacteria suggesting a disparity in the selectivity of the test systems. All compounds showed direct genotoxicity in the Vibrio test, but amitraz and its metabolite were genotoxic at concentrations 10(3)-10(5) lower than all the other compounds. The observations indicate that stable aniline degradation products of the pesticides may contribute considerably to environmental risks of pesticides application and that genotoxic effects may arise upon degradation of pesticides.
Amitraz's production may result in its release to the environment through various waste streams; its use as an acaricide, insecticide(1) will result in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), a Koc range of 1000(2) to 2000(3) indicates that amitraz is expected to have low mobility in soil(SRC). The pKa of amitraz is 4.20(3), indicating that this compound will partially exist in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). However, moderate mobilty has been reported in some soils(5). Volatilization of amitraz from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.87X10-6 atm-cu m/mole(3). Amitraz is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.0X10-6 mm Hg at 25 °C(2). A biodegradation half-life in soil of 1 day(5) suggests that biodegradation is an important environmental fate process in soil(SRC).|FIELD: Amitraz breaks down rapidly in the environment with a reported half-life of 1 day; it forms BTS 27271 (N-(2,4-dimethylphenyl)-N"-methylformamide)(2) and BTS 27919 (2,4-dimethylphenylformamide)(3). However these products are more persistent than the parent with half-lives ranging from 17 to 110 days and 70 to 150 days, respectively(1).|AQUATIC FATE: Based on a classification scheme(1), a Koc range of 1000(2) to 2000(3) indicates that amitraz is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 9.87X10-6 atm-cu m/mole(3). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 6.5 and 53 days, respectively(SRC). According to a classification scheme(5), measured BCF values of 588-1,838(6) suggest bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). A biodegradation half-life in soil of 1 day(6) suggests that biodegradation may be an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), amitraz, which has a vapor pressure of 2.0X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase amitraz 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 0.95 hours(SRC), calculated from its rate constant of 1.3X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase amitraz may be removed from the air by wet or dry deposition(SRC). UV light appears to have little affect on stability(4).
The rate constant for the vapor-phase reaction of amitraz with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 0.95 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Amitraz is expected to undergo hydrolysis in the environment with reported half-lives at 25 °C of 2.1 hours at pH 5, 22.1 hours at pH 7, and 25.5 hours at pH 9(2). Hydrolysis of amitraz proceeds at any pH but the rate is faster towards the acidic pH range. The primary hydrolysis degradation products are 2,4-dimethylaniline at very acidic pH (pH<3), N-(2,4-dimethylphenyl)-N'-methylformamidine and 2,4-dimethylformamidine at less acidic pH (pH 3-6), and 2,4-dimethylphenylformamidine at basic pH(3). The acid-stable hydrolytic product 2,4-dimethylphenylformamide will further hydrolyze to 2,4-dimethylaniline, with more rapid degradation occurring under basic conditions(4). UV light appears to have little affect on stability(2). Photolysis rates of 131/day at <30 °C in soil and 0.173/day at 25 °C in water have been reported(5).|Amitraz hydrolysis(1),[Table#6513]
Measured BCF values of 588-1,838 in bluegill sunfish have been reported for amitraz(1). According to a classification scheme(2), these BCF values suggest bioconcentration in aquatic organisms is high to very high(SRC), provided the compound is not metabolized by the organism(SRC).
1.00e+03 L/kg|The Koc of amitraz was reported to range from 1,000(1) to 2000(2). According to a classification scheme(3), this Koc value indicates amitraz will have low mobility in soil. Although it is considered to be moderately mobile in some soils (batch equilibrium studies indicated moderate mobility in sandy loam, silt loam and clay soils and very mobile in clay soils), amitraz degrades rapidly and therefore is not considered to be a serious concern for groundwater contamination(4). Amitraz had measured Freundlich adsorption coefficients of 1.69 in a Shelby sandy soil, 3.01 in a Spencer sand, 89.13 in a Terling clay and 16.31 in a Shelford clay(4). The pKa of amitraz is 4.20(2), indicating that this compound will partially exist in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5).
The Henry's Law constant for amitraz is 9.87X10-6 atm-cu m/mole(1). This Henry's Law constant indicates that amitraz is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 6.5 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 52.9 days(SRC). Amitraz is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.0X10-6 mm Hg(3).
Amitraz was detected in 19 of 221 samples of honey collected in Spain in 1988-1991, at concns ranging from 33 ng/kg to 1820 ng/kg, with an average concn of 420 ng/kg(1). Amitraz, applied at the field recommended dose to tea, was 90% dissipated within 10 days after application. After the 10th day the residue persisted in the range of 0.15-0.27 ppm(2).
Occupational exposure to amitraz may occur through inhalation and dermal contact with this compound at workplaces where amitraz is produced or used. Limited monitoring and use data indicate that the general population may be exposed to amitraz via inhalation or ingestion of certain imported foods and dermal contact with consumer products containing amitraz. (SRC)
Drug Information
Treatment and prevention of infestations in dogs by ticks (Ixodes ricinus, Dermacentor reticulatus, Rhipicephalus sanguineus, Ixodes scapularis, Dermacentor variabilis, Haemaphysalis elliptica, Haemaphysalis longicornis, Amblyomma americanum and Amblyomma maculatum) and fleas (Ctenocephalides felis and Ctenocephalides canis). Treatment of infestations by chewing lice (Trichodectes canis). Prevention of environmental flea contamination by inhibiting the development of all flea immature stages. The product can be used as part of a treatment strategy for the control of flea-allergy dermatitis. Elimination of fleas and ticks within 24 hours. One treatment prevents further infestations for five weeks by ticks and for up to five weeks by fleas.The treatment indirectly reduces the risk of transmission of tick-borne diseases (canine babesiosis, monocytic ehrlichiosis, granulocytic anaplasmosis and borreliosis) from infected ticks for four weeks.|For the treatment and prevention of infestations by fleas (Ctenocephalides canis and C. felis), and ticks (Ixodes ricinus, Ixodes hexagonus, Rhipicephalus sanguineus, Dermacentor reticulatus and Dermacentor variabilis), and treatment of demodicosis (caused by Demodex spp.) and lice (Trichodectes canis) in dogs.The veterinary medicinal product can be used as part of a treatment strategy for flea allergy dermatitis (FAD).
MEDICATION (VETERINARY): Amitraz ... is used primarily as an acaricide to control ticks and mites. It is available as a dip for control of canine demodicosis and will also control scabies. An amitraz-impregnated collar is also marketed for the control of ticks on dogs. More recently, an amitraz-containing spot-on product for control of ectoparasites in dogs was developed. It combines the action of amitraz against ticks, mites, and demodectic and sarcoptic mange with that of metaflumizone, a sodium channel blocker, broadening the spectrum of activity by adding efficacy against fleas and lice. Amitraz is not approved for use on cats.|MEDICATION (VETERINARY): A 2.5-yr-old female llama (Lama glama) ... with skin lesions was presented to the Animal Health Center in Seoul Grand Park Zoo, Korea. Mites of the genus Demodex in the absence of other mites or fungi were identified from the lesions by skin scrapings. ... Treatment with amitraz (0.025%) eliminated the mites and resolved the clinical signs.
Compounds that bind to and activate ADRENERGIC ALPHA-2 RECEPTORS. (See all compounds classified as Adrenergic alpha-2 Receptor Agonists.)|Chemicals that, while not possessing inherent pesticidal activity, nonetheless promote or enhance the effectiveness of other pesticides when combined. (See all compounds classified as Pesticide Synergists.)|Substances causing insects to turn away from them or reject them as food. (See all compounds classified as Insect Repellents.)|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.)
In all species examined, urine was the major route of excretion, accounting for 65-84% of the dose (55-76% within the first 24 hr). ... In both rats and mice, increasing the dose of amitraz from 1 to 100 mg/kg bw increased the excretion of N-methyl- N'-(2,4-xylyl)formamidine from approximately 5 to 30% of the total excretion.|In separate studies, groups of two male and two female beagle dogs were dosed orally (4 mg/kg bw by capsule) or dermally (20-21 mg on an area of 400-500 cm sq) with (14)C-amitraz (specific activity, 8.6 mCi/g). Peak blood concentrations of radiolabel were observed during the first 8 hr after oral administration. About 80% of the oral dose was excreted within the first 24 hr and 100% within 72 hr, preferentially in the urine. After dermal treatment, peak blood concentrations occurred within 24-72 hr, and only 25-40% was recovered in urine and feces over a 10-day collection period, demonstrating the poor dermal absorption of amitraz.
Analysis of urine obtained from volunteers dosed with (14)C-amitraz indicated that the metabolism of amitraz was qualitatively similar to that in the other species. The major metabolites were 4-formamido- meta-toluic acid, 4-acetamido- meta-toluic acid and N-methyl- N'-(2,4-xylyl)formamidine. In addition, 40-60% of the metabolites excreted in urine were accounted for by a polar fraction containing conjugates of 4-formamido- meta-toluic acid and 4-acetamido- meta-toluic acid. The minor metabolites included 4-amino- meta-toluic acid and form-2',4'-xylidide. Excretion of N-methyl- N'-(2,4-xylyl)formamidine was dose-dependent. The metabolites identified in the volunteers were 4-formamido- meta-toluic acid plus 4-acetamido- meta-toluic acid (27% of the total radiolabel in urine), N-methyl- N'-(2,4-xylyl)formamidine (6%), 4-amino- meta-toluic acid (4%), form-2',4'-xylidide (4 %), the product of acid hydrolysis of N-methyl- N'-(2,4-xylyl)formamidine and form-2',4'-xylidide (1%), and polar material (57%).|When (14)C-amitraz was applied to Boophilus microplus, penetration occurred readily. Cleavage to 2,4-dimethylformanilide and N-2,4-dimethylphenyl N'-methylformamidine and large amounts of polar material occurred. 2,4-dimethylaniline adn CO2 were also produced.|... Pear samples were extracted with ethyl acetate and anhydrous sodium sulphate. Amitraz was found to be rapidly decomposed into four related compounds, of which N-(2,4-dimethylphenyl)formamidine (DMPF) was the most abundant and persistent. N,N'-bisdimethylphenylformamidine (BDMPF), 2,4-dimethylformamidine (DMF) and 2,4-dimethyl aniline (DMA) were also main metabolites of amitraz.|In separate studies, groups of two male and two female beagle dogs were dosed orally (4 mg/kg bw by capsule) or dermally (20-21 mg on an area of 400-500 cm sq) with (14)C-amitraz (specific activity, 8.6 mCi/g). ... /The/ metabolism of amitraz was essentially the same after oral and dermal administration. 4-Formamido- meta-toluic acid was the predominant residue in both blood and urine. The parent compound and the first hydrolysis products, N-methyl- N'-(2,4-xylyl)formamidine and form-2',4'-xylidide, were not observed at measurable concentrations in either blood or urine.|The hydrolyzed metabolic products of amitraz include 2,4-dimethylaniline, and N-(2,4-dimethylphenyl)-N'-methylformamidine. These metabolites are further metabolized to 2,4-dimethylaniline and ultimately to 4-amino-3-methylbenzoic acid, the principal amitraz metabolite found in the urine and liver.
Amitraz exhibits monoamine oxidase-inhibiting properties in vitro, but only at high doses does it or its main metabolite (n-2,4 dimethylphenyl-N-methyl-formamide-- BTS27-271) exhibit central; monoamine oxidase-inhibiting properties in animals in vivo. The hydrolyzed metabolic product 2,4-dimethylaniline is a relatively weak methemoglobin formed in dog and presumably man. Topical application of high doses of amitraz in the dog incr plasma glucose and suppresses insulin. Amitraz appears to be a central alpha-adrenoceptor agonist whose action results in diminished peripheral sympathetic tone with a lowering of blood pressure and heart rate. Peripherally, it exhibits both alpha1 and alpha2 adrenoceptor agonist activity resulting in some elevation of blood pressure. The xylene present in amitraz formulations is more likely to induce central nervous system depression.
Fresh air, rest. Seek medical attention if you feel unwell.
Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .
Rinse with plenty of water (remove contact lenses if easily possible). Refer for medical attention.
Airway protection. Ensure that a clear airway exists. Intubate the patient and aspirate the secretions with a large-bore suction device if necessary. Administer oxygen by mechanically assisted pulmonary ventilation if respiration is depressed. Improve tissue oxygenation as much as possible before administering atropine, to minimize the risk of ventricular fibrillation. In severe poisonings, it may be necessary to support pulmonary ventilation mechanically for several days. /N-methyl carbamate insecticides/|Atropine. Administer atropine sulfate intravenously, or intramuscularly if intravenous injection is not possible. Remember that atropine can be administered through an endotracheal tube if initial IV access is difficult to obtain. Carbamates usually reverse with much smaller dosages of atropine that those required to reverse organophosphates. The objective of atropine antidotal therapy is to antagonize the effects of excessive concentrations of acetylcholine at end-organs having muscarinic receptors. Atropine does not reactivate the cholinesterase enzyme or accelerate excretion or breakdown of carbamate. Recrudescence of poisoning may occur if tissue concentrations of toxicant remain high when the effect of atropine wears off. Atropine is effective against muscarinic manifestations, but is ineffective against nicotinic actions, specifically, muscle weakness and twitching and respiratory depression. Despite these limitations, atropine is often a life-saving agent in N-methyl carbamate poisonings. Favorable response to a test dose of atropine ... given intravenously can help differentiate poisoning by anticholinesterase agents from other conditions such as cardiogenic pulmonary edema and hydrocarbon ingestion. However, lack of response to the test dose, indicating no atropinization (atropine refractoriness), is characteristic of moderately severe to severe poisoning and indicates a need for further atropine. If the test dose does not result in mydriasis and drying of secretions, the patient can be considered atropine refractory. /N-methyl carbamate insecticides/|Skin decontamination. In patients with contaminated skin, clothing, hair, and/or eyes, decontamination must proceed concurrently with what ever resuscitative and antidotal measures are needed to preserve life. Flush the chemical from eyes with copious amounts of clean water. For asymptomatic individuals who are alert and physically able, a prompt shower and shampoo may be appropriate for thorough skin decontamination, provided the patient is carefully observed to insure against sudden appearance of poisoning. If there are any indications of weakness ataxia or other neurologic impairment, clothing should be removed and a complete bath and shampoo given while the victim is recumbent, using copious amounts of soap and water. Attendants should wear rubber gloves as vinyl provides no protection against skin absorption. Wash the chemical from skin folds and from under fingernails. Contaminated clothing should be promptly removed, bagged, and laundered before returning. Contaminated leather shoes should be discarded. Note that the pesticide can contaminate the inside surfaces of gloves, boot, and headgear. /N-methyl carbamate insecticides/|Gastrointestinal decontamination. If N-methyl carbamate has been ingested in a quantity probably sufficient to cause poisoning, consideration should be given to gastrointestinal decontamination ... . If the patient has presented with a recent ingestion and is still asymptomatic, adsorption of poison with activated charcoal may be beneficial. In significant ingestions, diarrhea, and/or vomiting are so constant that charcoal adsorption and catharsis are not indicated. Attention should be given to oxygen, airway management, and atropine. /N-methyl carbamate insecticides/|For more Antidote and Emergency Treatment (Complete) data for AMITRAZ (16 total), please visit the HSDB record page.
/HUMAN EXPOSURE STUDIES/ In a double-blind, randomized cross-over study, six healthy male volunteers aged 18-45 years and weighing 60-70 kg received sequential single oral doses of 0, 0.063, and 0.13 mg/kg bw amitraz, two to three weeks apart. Each dose was given with 150 mL water, 30 min after breakfast. Pulse rate, respiration rate, blood pressure, and temperature were measured at - 1, - 0.5, 1, 3, 6, 12, 24, and 36 hr, and electrocardiograms were performed at -1, 1, 3, 6, 12, 24, and 36 hr with respect to dosing. Pupil responsiveness and psychomotor performance were evaluated before treatment and at 2.5 and 8 hr. Urine was collected at 0-36 h and 36-60 hr. There were no clinically significant changes in vital signs or electrocardiographic parameters. Moreover, hematological, blood chemical, and urinary parameters, pupil responsiveness, and psychomotor performance were unaffected by treatment. The NOAEL was 0.13 mg/kg bw, the highest dose tested.|/HUMAN EXPOSURE STUDIES/ Two human volunteers who received a single oral dose of 0.25 mg/kg bw 14C-amitraz showed drowsiness, disorientation, slurred speech, decreased pulse rate and blood pressure, and other effects.|/SIGNS AND SYMPTOMS/ Clinical signs and symptoms after human exposure to an amitraz formulation initially include drowsiness, loss of consciousness, confused mental state, or agitation, with weakness, headache, vomiting, and malaise. Absent bowel sounds, miosis or mydriasis, abdominal pain and tenderness, and hyperactive deep tendon reflexes have been observed in children. Exposure to amitraz formulations in man may terminate fatally. ...|/SIGNS AND SYMPTOMS/ ... Amitraz poisoning is a rare disorder characterized by central nervous system (CNS) and respiratory depression, bradycardia, hypotension, hypothermia, hyperglycemia,nausea and vomiting. Poisoning may occur ... by oral, inhalation and dermal route.|For more Human Toxicity Excerpts (Complete) data for AMITRAZ (26 total), please visit the HSDB record page.
amitraz
The substance can be absorbed into the body by inhalation and by ingestion.
Transient skin flushing.
Amitraz Use and Manufacturing
It is prepared by reacting 2, 4-dimethylaniline, triethyl orthoformate and methylamine. Raw material consumption quota: 2, 4-dimethylaniline (100%) 350kg/t, triethyl orthoformate (100%) 500kg/t, monomethylamine 70kg/t, xylene 750kg/t.
Broad-spectrum acaricide is mainly used for the prevention and control of mites in crops such as fruit trees, cotton and vegetables, and it can also be used for the prevention and control of acarids in cattle, sheep and other livestock. This product is a broad-spectrum acaricide. Mainly used for fruit trees, flowers, strawberries and other agricultural and horticultural crops. Prevents and controls mites, especially for citrus mites. It is also used to control cotton bollworm and red bollworm; control ticks, mites and scabies of domestic animal parasites. Amitraz is a kind of acaricide with better efficacy in Chinese medicine. Calibration instruments and devices; evaluation methods; working standards; quality assurance/quality control; others.
USEPA/OPP Pesticide Code 106201; Trade Names: Baam, Triazid,U-36059, BTS-27419, ENT 27967, MITAC.|Emulsifiable concentrate; wettable powder.|Premix Partners: Bifenthrin; Tralomethrin.|Formulations include the following: METABAN liquid concentration- amitraz, xylene, propylene oxide, blend of alkyl benzene sulfonates, and ethoxylated polyethers. MITAC 20 EC- Amitraz in 75% xylene. In Turkey some amitraz formulations contain 20% amitraz, and some veterinary formulation may contain 12.5 to 13.6% amitraz. The amount of xylene as a solvent varies between 30 and 70%.|For more Formulations/Preparations (Complete) data for AMITRAZ (11 total), please visit the HSDB record page.
The WHO Recommended Classification of Pesticides by Hazard identifies amitraz (technical grade) as Class II: moderately hazardous; Main Use: acaricide.|Registered uses on cotton and pears have been cancelled|Registered uses on beef and dairy cattle, and hogs for tick, mite and lice management .. Formulations may be used to treat the walls and surfaces of swine houses ... used to treat ticks on dogs via amitraz-impregnated dog collars
Product analysis by glc ... Residue analysis also by glc with ECD ... Residues in soil by gc with NPD.|FDA Method 242.1. Organonitrogen Residues General Method for Nonfatty Foods Including Acetone Extraction and Isolation in Organic Phase.
Agrochemicals -> Acaricides, Insecticides|Veterinary drugs -> Certifect -> EMA Drug Category|Ectoparasiticides for topical use, incl. insecticides -> Veterinary pharmacotherapeutic group|Veterinary drugs -> ProMeris Duo -> EMA Drug Category|Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients|Veterinary substances, Acaricides, Insecticides|Pesticides -> Insecticides|Environmental transformation -> Pesticides (parent, predecessor)
Amitraz has known environmental transformation products that include 2,4-dimethylphenylformamide and N'-(2,4-Dimethylphenyl)-N-methylformamidine.|Amitraz has known environmental transformation products that include 2,4-dimethylformanilide and N-(2,4-dimethylphenyl)-N-methyl-formamidine.
Computed Properties
Molecular Weight:293.4
XLogP3:5.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:293.189197746
Monoisotopic Mass:293.189197746
Topological Polar Surface Area:28
Heavy Atom Count:22
Complexity:354
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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