ChemicalBook CAS DataBase List 33089-61-1

33089-61-1

Name	Amitraz
CAS	33089-61-1
EINECS(EC#)	251-375-4
Molecular Formula	C19H23N3
MDL Number	MFCD00069396
Molecular Weight	293.41
MOL File	33089-61-1.mol

Synonyms

1,5-di(2,4-dimethylphenyl)-3-methyl-1,3,5-triazapenta-1,4-diene AMITAC AMITRAZ AURORA KA-686 BAAM(R) BTS 27419 BYEBYE EDRIZAR ENT 27967 ISOKA methyl-bis(2,4-xylyliminomethyl)amine MITAC MITAC(R) N'-(2,4-DIMETHYLPHENYL)-N-[[(2,4-DIMETHYLPHENYL)IMINO]METHYL]-N-METHYLMETHANIMIDAMIDE N-METHYL-N'-2,4-XYLYL-N-(N-2,4-XYLYLFORMIMIDOYL)-FORMAMIDINE N'-N'-[(METHYLIMINO)-DIMETHYLIDINE]-BIS-(2,4-XYLIDINE) PARSEC RACET SENDER TAKTIC

Chemical Properties

Appearance	Amitraz forms colorless needle-like crystals. Liquid formulations may contain flammable organic solvents.
Melting point	86-87°C
Boiling point	425.25°C (rough estimate)
density	1.1280
vapor pressure	3.4×10^-4 Pa (25 °C)
refractive index	1.5892 (estimate)
storage temp.	0-6°C
solubility	DMF: 30 mg/ml; DMF:PBS (pH 7.2) (1:2): 0.33 mg/ml; DMSO: 20 mg/ml; Ethanol: 2 mg/ml
form	Powder/Solid
pka	4.2 (weak base)
Water Solubility	0.08 mg l^-1
color	White
λmax	247nm(lit.)
Merck	13,486
Henry's Law Constant	1.0×10⁰ mol/(m³Pa) at 25℃, MacBean (2012)
Major Application	agriculture environmental
InChI	1S/C19H23N3/c1-14-6-8-18(16(3)10-14)20-12-22(5)13-21-19-9-7-15(2)11-17(19)4/h6-13H,1-5H3/b20-12+,21-13+
InChIKey	QXAITBQSYVNQDR-ZIOPAAQOSA-N
SMILES	CN(\C=N\c1ccc(C)cc1C)\C=N\c2ccc(C)cc2C
CAS DataBase Reference	33089-61-1(CAS DataBase Reference)
NIST Chemistry Reference	Amitraz(33089-61-1)
EPA Substance Registry System	33089-61-1(EPA Substance)

Safety Data

Symbol(GHS)	GHS07,GHS08,GHS09
Signal word	Warning
Hazard statements	H302-H317-H373-H410
Precautionary statements	P260-P273-P280-P301+P312-P302+P352-P314
Hazard Codes	Xn;N,N,Xn
Risk Statements	R22:Harmful if swallowed. R43:May cause sensitization by skin contact. R48/22:Harmful: danger of serious damage to health by prolonged exposure if swallowed . R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . less more
Safety Statements	S22:Do not breathe dust . S24:Avoid contact with skin . S36/37:Wear suitable protective clothing and gloves . S60:This material and/or its container must be disposed of as hazardous waste . S61:Avoid release to the environment. Refer to special instructions safety data sheet . less more
RIDADR	UN 3077
WGK Germany	3
RTECS	ZF0480000
REACH Registrations	Inactive
HazardClass	9
PackingGroup	III
HS Code	29252900
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Aquatic Acute 1 Aquatic Chronic 1 Skin Sens. 1 STOT RE 2
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) less more

Raw materials And Preparation Products

Hazard Information

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.

Reactivity Profile

Unstable in acid.

Air & Water Reactions

Insoluble in water.

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.

Shipping

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

Incompatibilities

Description

Amitraz is an amidine acaricide and insecticide. It is volatile, almost insoluble in water and, based on its chemical properties, is only slightly mobile with a low potential for leaching to groundwater. It is not persistent in soil systems, degradation being very rapid and would also not be expected to persistent in surface water under normal conditions. Amitraz has a moderate mammalian toxicity and there is some concern regarding its potential for bioaccumulation. It is considered to be a neurotoxin. Amitraz has a high to moderate toxicity to most terrestrial and aquatic species, the main exception being algae for which amitraz has a low level of toxicity.

Chemical Properties

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

Chemical Properties

Beige to Pale Yellow Solid

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.

Originator

Aludex,Hoechst Roussel Vet Ltd.

Uses

Acaricide; insecticide.

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.

Uses

Amitraz is used for the control of all stages of mites and insects such as aphids and whitefly, and the eggs and first instar larvae of Lepidoptera on fruit, cotton and vegetables. It is also used in honey bee hives and for the control of ticks, mites and lice on domestic and farm animals.

Uses

coccidiostat, antiplatelet

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.

Production Methods

The production of amitraz, a formamidine pesticide, typically involves a one-pot synthesis using 2,4-dimethylaniline, N-methylformamide, and triethyl orthoformate as starting materials. The mixture is heated to around 120 DegC for several hours, during which the reaction forms the amitraz compound and ethanol is volatilised.

Manufacturing Process

A mixture of 55.1 g 2,4-dimethylaniline hydrochloride, 83.7 g ptoluenesulphonyl chloride and 150 ml N-methylformamide was stirred with occasional cooling to maintain the temperature at 20°-35°C. When the exothermic reaction had subsided, the mixture was stirred at room temperature for 4 h, poured into a mixture of ice and water, and basified with 10 N sodium hydroxide solution, keeping the temperature of the mixture below 10°C. The precipitated solid was filtered, washed with water until free from alkali, dried at room temperature, to give N-2,4-dimethylphenyl-N'- methylformamidine, melting point 75°-76°C (recrystallized from cyclohexane).
A solution of 19.4 g N-2,4-dimethylphenyl-N'-methylformamidine and 0.3 g ptoluenesulphonic acid in 195 ml dry xylene was refluxed under anhydrous conditions for 48 h, causing the evolution of methylamine. The xylene was distilled off under reduced pressure to give 1,5-di-(2,4-dimethylphenyl)-3- methyl-1,3,5-triaza-penta-1,4-diene, melting point 88°-89°C (crystallized twice from isopropyl).

Therapeutic Function

Acaricide, Scabicide, Tickicide, Appetite stimulant

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®

Mechanism of action

Non-systemic having contact and respiratory action. Acts on nervous system. Octopamine receptor agonist.

Pharmacology

The mechanism of action of amitraz has not been completely elucidated, and, presently, a dual mode of action appearsmost likely. Firstly, the enzymemonoamine oxidase, which metabolizes neurotransmitter amines in mites and ticks, is inhibited. Secondly, octopamine receptors in the central nervous system of ectoparasites are activated by amitraz, thereby modifying tonic muscle contractions. The effect of amitraz is to induce increased neuronal activity, abnormal behavior, detachment, and death of mites and ticks.

Veterinary Drugs and Treatments

In dogs, amitraz solution is used topically primarily in the treatment of generalized demodicosis. A topical spot-on solution (ProMeris? for Dogs) and a collar (Preventic?) are available for treatment and prevention of flea and tick infestation. It is also used as a general insecticidal/ miticidal agent in several other species (see label information). The pharmacologic action of amitraz is not well understood, but it is a monoamine oxidase (MAO) inhibitor (in mites) and may have effects on the CNS of susceptible organisms. It apparently also possesses alpha-2 adrenergic activity and inhibits prostaglandin synthesis. Amitraz can cause a significant increase in plasma glucose levels, presumably by inhibiting insulin release via its alpha2-adrenergic activity. Yohimbine (alpha2 blocker) or atipamezole can antagonize this effect.

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.

Metabolism

Amitraz is poorly absorbed when applied topically to animals. By contrast, orally administered amitraz is rapidly and extensively absorbed. The metabolism and excretion of amitraz are also rapid. It is hydrolyzed to N-(2,4-dimethylphenyl)-N -methyl formamidine and 2,4- dimethyl formamidine and the final product, 4-amino-3- methylbenzoic acid, is converted to non-toxic conjugates. The latter are excreted in the urine and, to a lesser extent, in bile.

Degradation

Amitraz is readily hydrolysed at acidic pH but is relatively stable under alkaline conditions. Its DT₅₀ values at 25 °C at pH 5,7 and 9 are given as 2.1,22.1 and 25.5 hours, respectively (PM). A recent study (Pierpoint et aE., 1997) as part of the development of a vat management and waste disposal programme for animal dips describes the kinetics and mechanism of hydrolysis of amitraz in detail. Pseudo-first-order rate constants are given for six pH values between 3.24 and 9.12. The DT₅₀ values at pH values 3.24, 5.09 and 9.12 were respectively 0.4, 8.7 and 112 hours. The reaction was mainly acid-catalysed with a small unassisted component. There was no base catalysis. One of the primary products (Scheme 1) was N-2,4 dimethylphenyl-N-methylformamidine( 2); however, at low pH this was not detected because it was rapidly hydrolysed to 2,4-dimethylphenylformamide (3). Some direct hydrolysis of amitraz to product 3 was also seen. The latter underwent slow base-catalysed hydrolysis to 2,4 dimethylaniline (4). This was a much slower reaction with a DT₅₀ (pH 9.12) of about 300 days.

Toxicity evaluation

Amitraz displays serotonin (5-hydroxytryptamine) blocking activity and a2-adrenoceptor agonist activity in animals. The clinical signs associated with intoxication in dogs include sedation, bradycardia, hypotension, hyperglycaemia, hypothermia, and mydriasis. The specific antidote for animal toxicity is the a2-adrenoceptor antagonist, yohimbine. The toxicity profile of amitraz in the horse includes transient sedation and intestinal stasis that can progress to impaction colic (79). For this reason, amitraz is not approved for use in this species in any country.

References

[1] Patent: CN107778200, 2018, A. Location in patent: Paragraph 0079-0104

Pesticide Type

Insecticide; Acaricide; Veterinary substance

Material Safety Data Sheet(MSDS)

Questions And Answer

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.
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33089-61-1

Chemical Properties

Safety Data

Raw materials And Preparation Products

Raw materials

Preparation Products

Hazard Information

General Description

Reactivity Profile

Air & Water Reactions

Potential Exposure

First aid

Shipping

Incompatibilities

Description

Chemical Properties

Chemical Properties

Waste Disposal

Originator

Uses

Uses

Uses

Uses

Definition

Production Methods

Manufacturing Process

Therapeutic Function

Agricultural Uses

Trade name

Mechanism of action

Pharmacology

Veterinary Drugs and Treatments

Metabolic pathway

Metabolism

Degradation

Toxicity evaluation

References

Pesticide Type

Material Safety Data Sheet(MSDS)

Questions And Answer

Overview

Indication and contradiction

Pharmacokinetics and pharmacodynamic

Reference

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