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Amitraz

Overview Indication and contradiction Pharmacokinetics and pharmacodynamic Reference
Amitraz
Amitraz structure
CAS No.
33089-61-1
Chemical Name:
Amitraz
Synonyms
baam;bipin;RACET;ZAMIR;ISOKA;MITAC;acarac;TAKTIC;SENDER;AMITAC
CBNumber:
CB9680920
Molecular Formula:
C19H23N3
Formula Weight:
293.41
MOL File:
33089-61-1.mol

Amitraz Properties

Melting point:
86-87°C
Boiling point:
425.25°C (rough estimate)
Density 
1.1280
refractive index 
1.5892 (estimate)
storage temp. 
0-6°C
form 
Powder/Solid
color 
White
λmax
247nm(lit.)
Merck 
14,486
InChIKey
QXAITBQSYVNQDR-ZIOPAAQOSA-N
CAS DataBase Reference
33089-61-1(CAS DataBase Reference)
NIST Chemistry Reference
Amitraz(33089-61-1)
EPA Substance Registry System
Methanimidamide, N'-(2,4-dimethylphenyl)- N-[[(2,4-dimethylphenyl)imino] methyl]-N-methyl-(33089-61-1)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes  Xn;N,N,Xn
Risk Statements  22-43-48/22-50/53
Safety Statements  22-24-36/37-60-61
RIDADR  UN 3077
WGK Germany  3
RTECS  ZF0480000
HazardClass  9
PackingGroup  III
Hazardous Substances Data 33089-61-1(Hazardous Substances Data)
Toxicity LD50 in male rats, female mice, rabbits, guinea pigs, bobwhite quail (mg/kg): 800, >1600, >100, >400, 788 orally; LD50 in rabbits, male rats (mg/kg): >200, >1600 dermally; LC50 (48 hr) in rainbow trout, Japanese carp: 3.3, 1.2 ppm (Labonne)
Symbol(GHS):
Signal word: Warning
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H302 Harmful if swallowed Acute toxicity,oral Category 4 Warning P264, P270, P301+P312, P330, P501
H317 May cause an allergic skin reaction Sensitisation, Skin Category 1 Warning P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H373 May cause damage to organs through prolonged or repeated exposure Specific target organ toxicity, repeated exposure Category 2 Warning P260, P314, P501
H410 Very toxic to aquatic life with long lasting effects Hazardous to the aquatic environment, long-term hazard Category 1 Warning P273, P391, P501
Precautionary statements:
P260 Do not breathe dust/fume/gas/mist/vapours/spray.
P273 Avoid release to the environment.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P391 Collect spillage. Hazardous to the aquatic environment
P333+P313 IF SKIN irritation or rash occurs: Get medical advice/attention.
P501 Dispose of contents/container to..…

Amitraz price More Price(2)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 45323 Amitraz PESTANAL 33089-61-1 250mg $26.8 2018-11-20 Buy
Sigma-Aldrich 1028000 Amitraz United States Pharmacopeia (USP) Reference Standard 33089-61-1 200mg $338.1 2018-11-20 Buy

Amitraz Chemical Properties,Uses,Production

Overview

Amitraz is a formamidine pesticide widely used as an insecticide and acaricide. Formamidine pesticides were developed in the late 1950s and early 1960s due to the development of resistances to conventional insecticides. The two formamidines primarily marketed and most widely used are chlordimeform and amitraz. Amitraz (1,5-di (2,4-dimethylphenyl)-3-methyl-1, 3, 5-triazapenta1,4-diene) (Figure 1) was first patented in 1971, registered as a pesticide of technical grade in 1975[1] and marketed in 1981.
Amitraz is an insecticide used to prevent tick and mite infestation and is in common use around the world. Amitraz is applied to cattle[2] and sheep in dip baths at concentrations of 0.025%[3], to dogs from collars impregnated with 0.025% amitraz, or by topical application in a bath of 0.05% amitraz[4], to pigs in sprays containing 12.5%, and to cotton and hops[5] by spraying 20% solutions of amitraz from aeroplanes and ground sprinklers. In addition, amitraz is used to control psylla infestations of pears[6]. Human exposure to amitraz occurs when diluting the concentrate obtained from the manufacturer, when applying the amitraz to crops or animals, and when working in amitraz-treated areas, for example pear orchards or cotton fields[1].
Different agencies have evaluated amitraz toxicity and the lethal dose 50 (LD50) or lethal concentration 50(LC50) values on acute toxicity studies[1, 7]. The EPA (Environmental Protection Agency), according to acute toxicity studies, classifies amitraz as Class III-slightly toxic by the oral and inhalation routes, as Class II-moderately toxic by the dermal route, and as Class IV-not a dermal irritant and only slightly irritant to the eyes and not a dermal sensitizer[1].
Amitraz is rapidly absorbed, distributed, metabolized, and eliminated primarily via urine when administered orally to mammals.[1, 7] No differences have been described between species and genders in the rates and routes of excretion. In all species studied, 55−74% of the dose was excreted in the urine within the first 24 h after dosing[1, 7]. The degradation products present in the urine include N′-[2,4-dimethylphenyl]-Nmethylformamidine (BTS-27271), 2,4-dimethylformanilide (BTS-27919), 2,4-dimethylaniline (BTS-24868), 4-formamido3-methylbenzoic acid (BTS-39098), 4-amino-3-methylbenzoic acid (BTS-28369), and several unknown metabolites.[8] Moreover, the spectrum of metabolites observed was similar in all species studied. BTS-27271 and BTS-27919 are the main metabolites of amitraz and a cause of concern due to the content of the 2,4-dimethylaniline moiety, which could lead to developmental and genotoxic effects.[1, 2] Furthermore, BTS-27271 has been found to be more potent than amitraz with regard to its miticidal activity and mammalian toxicity. The action of these metabolites has been described only for some of the mechanisms and effects of amitraz; thus, further studies are needed to determine their participation in the rest of the mechanisms and effects[9, 10].

Figure 1 the chemical structure of amitraz

Indication and contradiction

Amitraz is indicated for animal use against mites, lice and ticks for cattle, swine and sheep. For dogs, it is used against ticks and mite[11]. It was reported as the drug of choice in the treatment of localized and generalized demodicosis in dogs[11]. Along with macrocyclic lactones such as milbemycin oxime, ivermectin, moxidectin, and doramectin, amitraz is still recommended for the treatment of generalized canine demodicosis, although it is not very efficient in adult-onset demodicosis cases[12]. Chesney (1989) also reported the use of amitraz in the treatment of demodicosis in cats[13]. Gunaratnam et al. (1983)[14] evaluated amitraz toxicity in cats, and concluded that low concentrations, around 0,0125% are capable of generating moderate toxic effects, especially anorexia. The toxic effects are even more evident in cats, due to their licking habit, resulting in a higher intake of the product. However, it is possible to use amitraz topically in healthy cats, respecting the appropriate contraindications common to the other species, which is to avoid the use in diabetic, hypothermic, and cardiac patients.
Amitraz is contraindicated in horses due to the risk of hypomotility and intestinal atony, leading to severe intestinal impaction[13, 14]. It has been also observed, besides the intestinal symptoms, the occurrence of neurologic signs as drowsiness, decreased cranial nerve reflexes and ataxia in horses submitted to the experimental use of amitraz. This substance is contraindicated for patients with extended skin injuries, which could lead to an over absorption, favoring intoxication.

Pharmacokinetics and pharmacodynamic

Amitraz is quickly hydrolyzed in an acid environment when it is orally administrated, due to its instability in this environment. The hydrolysis in a low pH generates the compound 2,4-dimethylphenyl formamide, which is stable in an acid environment. This substance can still be hydrolyzed, generating 2,4-dimethylaniline[15]. Absorption is effective through the skin, which may be major or minor depending on its integrity, the occurrence of injuries, and inflammation. After reaching the blood stream, the drug reaches the highest plasmatic level in up to two hours. The biotransformation occurs in the liver, generating the active metabolite BTS 27271, the most important pharmacologically, because it acts directly in the regulation of the insulin and glucagon secretion by binding to the α2A and α2D-adrenergic receptors, inhibiting insulin and stimulating glucagon secretion, resulting in hyperglycemia. Metabolites are excreted in bile and urine.
In insects, formamidines such as chlordimeform and amitraz operate its toxic effects by interacting with octopaminergic receptors in the central nervous system[16]. The mechanisms by which the deleterious effects of amitraz in mammals are determined are based on its agonistic action on α2-adrenergic receptors and inhibitory action over the monoamine oxidase (MAO), but there are reports of various action pathways, such as: H1 histamine receptor inhibition, prostaglandin synthase inhibition, adenylyl cyclase inhibition, voltage-gated calcium channels activation, reactive oxygen species generation, cell death induction and endocrine disruptions. Amitraz is also related to the emergence of neurotoxic effects and modifications in the reproductive sphere in rats[17].

Reference

  1. USEPA (United States Environmental Protection Agency) (1996)
  2. McDougall K and Lewis I (1984). Aust Vet J 61,137–140.
  3. Eamens G, Spence S and Turner M (2001) Aust Vet J 79,703–706.
  4. Shaw S and Foster A (2000) Aust Vet J 78,243–244.
  5. Weichel L and Nauen R (2003) Pest Manage Sci 59,991–998.
  6. Schaub L, Sardy S and Capkun G (2002) Pest Manage Sci 58,959–963.
  7. JMPR. Pesticide Residues in Food−1998, Evaluations Part II: Toxicological WHO/PCS/99.18, 1998
  8. Knowles, C. O., and Benezet, H. J. (1981) J. Environ. Sci. Health, Part B 16, 547−555.
  9. Schuntner, C. A., and Thompson, P. G. (1978) Aust. J. Biol. Sci. 31, 141−148.
  10. Pass, M. A., and Mogg, T. D. (1991) Comp. Biochem. Physiol., Part C: Pharmacol., Toxicol. Endocrinol. 99, 169−172.
  11. Folz, S.D et al. Veterinary Parasitology, 16(3-4): 335–341, 1984.
  12. Mueller, R.S. Veterinary Dermatology, 15: 75-89, 2004
  13. Chesney, C.J. Journal of Small Animal Practice, 30(12): 689-695, 1989
  14. Gunaratnam, P.; Wilkinson, G.T.; Seawright, A.A. Australian Veterinary Journal, 60(9): 278–279, 1983.
  15. Pierpoint, A.C.; Hapeman, C.J.; Torrents, A. Journal of Agricultural and Food Chemistry's. 45(5): 1937-1939,1997.
  16. Chen, A.C.; He, H.; Davey, R.B. Veterinary Parasitology, 148: 379-383, 2007.
  17. Del Pino, J.; et al Chemical Research in Toxicology, 28(6): 1073-1094, 2015.
  18. Costa, L. G., Wu, D. S., Olibet, G., and Murphy, S. D. (1989) Neurotoxicol. Teratol. 11, 405−411.
  19. Douglas, W. W. (1980) Histamine and 5-Hydroxytryptamine (Serotonin) and Their Antagonist, in The Pharmacological Basis of Therapeutics., pp 609−646, Macmillan, New York.
  20. Levitt, P., et al. (1997) Trends Neurosci. 20, 269−274.
  21. Fajardo, A. M., et al (2014) Cancers 6, 436−458.
  22. Shin, D. H., and Hsu, W. H. (1994) Toxicol. Appl. Pharmacol. 128, 45−49.
  23. Radakovic, M., et al J. Biosci. (New Delhi, India) 38, 53−62.
  24. Gregorc, A., and Bowen, I. D. (2000) Cell Biol. Int. 24, 319−324.

Chemical Properties

Beige to Pale Yellow Solid

Chemical Properties

Amitraz forms colorless needle-like crystals. Liquid formulations may contain flammable organic solvents.

Uses

coccidiostat, antiplatelet

Uses

Amitraz is an antiparasitic used to control red spider mites, leaf miners and scale insects. This compound is active by inhibiting the targets monoaminooxidase enzyme.

Definition

ChEBI: 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.

Uses

Acaricide; insecticide.

General Description

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.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Unstable in acid.

Agricultural Uses

Insecticde, Acaricide, Veterinary medicine: Registered for control of pear psylla on pears, whitefly and mites on pears and cotton; cattle, dogs, sheep, and hog dip to control ticks, mange mites, lice and other pests. Not permitted on apples. Used to control red spider mites, leaf miners, scale insects, and aphids. Also used on cotton to control bollworms, white fly, leaf worms, and tobacco budworms. Not registered for use in EU countries

Trade name

AAZDIENO®; ACARAC®; ACADREX®; ARMY®; AZODIENO®; BAAM®; BOOTS BTS 27419®; BTS 27,419®; BUMETRAN®; COYOTE®; DANICUT®; ECTODEX®; EDRIZAN®; EDRIZAR®; GARIAL®; ISTAMBUL®; MITABAN®; MITAC®; OVASYN®; OVIDREX®; PARSEC®; ROTRAZ®; SENDER®; TAC-PLUS®; TACTIK®; TRIATIX®; TRIATOX®; TUDY®; VAPCOZIN TAKTIC®; UPJOHN U-36059®

Potential Exposure

Those engaged in the manufacture, formulation and application of this insecticide and acaricide. A rebuttable presumption against registration for amitraz was issued on April 6, 1977 by United States Environmental Protection Agency on the basis of oncogenicity. Incompatibilities: Keep away from strong oxidizers and strong acids. Acids may render this material unstable.

First aid

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.

Metabolic pathway

14C-Amitraz is applied on lemons grown under glasshouse conditions at final harvest and the applied radioactivity is quantitatively recovered, predominantly in the peel (86%). The total residue at harvest contains amitraz, N-methyl-N'-(2,4-xylyl)formamidine, and formyl-2',4'-xylydine and conjugates of 4-amino- m-toluic acid and the conjugated metabolites which are convertible to 2,4-xylidine. Amitraz is readily hydrolyzed at low pH values, forming acid-stable formyl-2,4-xylydine which can be further hydrolyzed to 2,4-xylidine.

Shipping

UN2763 Triazine pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Incompatibilities

Those engaged in the manufacture, formulation and application of this insecticide and acaricide. A rebuttable presumption against registration for amitraz was issued on April 6, 1977 by United States Environmental Protection Agency on the basis of oncogenicity. Incompatibilities: Keep away from strong oxidizers and strong acids. Acids may render this material unstable.

Waste Disposal

In accordance with 40CFR 165 recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.

Amitraz Preparation Products And Raw materials

Raw materials

Preparation Products


Amitraz Suppliers

Global( 225)Suppliers
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View Lastest Price from Amitraz manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-08-15 Amitraz
33089-61-1
US $1.00 / KG 1G 98% 100KG career henan chemical co
2019-03-26 33089-61-1 Amitraz 12.5% ec in veterinary medicine
33089-61-1
US $1.00-1.00 / KG 1 kg/桶 99% 20tons Hebei Jimi Trading Co., Ltd.
2018-07-10 Amitraz
33089-61-1
US $10.00-10.00 / KG 10KG 99% 10tons Hebei Chisure Biotechnology Co., Ltd.

Amitraz Spectrum


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