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2,4 - Xylidine, N,N' - (methyliminodimethylidyne) bis -

RTECS #: ZF0480000

CAS #: 33089-61-1

UPDATE: February 2009 MW: 293.45 MF: C19H23N3


NOTE:

TABLE OF CONTENTS:
  1. SYNONYMS:
  2. REPRODUCTIVE EFFECTS DATA:
  3. ACUTE TOXICITY DATA:
  4. OTHER MULTIPLE DOSE DATA:
  5. REVIEWS:
  6. STANDARDS AND REGULATIONS:
  7. STATUS IN FEDERAL AGENCIES:
  8. REFERENCES:

SYNONYMS:

  1. 1,5 - Di (2,4 - dimethylphenyl) - 3 - methyl - 1,3,5 - triazapenta - 1,4 - diene
  2. 2 - Methyl - 1,3 - di (2,4 - xylylimino) - 2 - azapropane
  3. Acarac
  4. Amitraz
  5. Amitraz estrella
  6. Amitraze (French)
  7. Azadieno
  8. Azaform
  9. BAAM
  10. BTS 27,419
  11. Bipin
  12. Boots BTS 27419
  13. ENT 27967
  14. Ectodex
  15. Edrizar
  1. Fumilat A
  2. Kenaz
  3. Methanimidamide, N' - (2,4 - dimethylphenyl) - N - ( ( (2,4 - dimethylphenyl) imino) methyl) - N - methyl -
  4. Mitaban
  5. Mitac
  6. N' - (2,4 - Dimethylphenyl) - N - ( ( (2,4 - dimethylphenyl) imino) methyl) - N - methylmethanimidamide
  7. N,N' - ( (Methylimino) dimethylidyne) di - 2,4 - xylidine
  8. N,N - Bis (2,4 - xylyliminomethyl) methylamine
  9. N,N - Di - (2,4 - xylyliminomethyl) methylamine
  10. N - Methyl - N' - 2,4 - xylyl - N - (N - 2,4 - xylylformimidoyl) formamidine
  11. N - Methyl - bis (2,4 - xylyliminomethyl) amine
  12. R.D. 27419
  13. Taktic
  14. U - 36059
  15. Upjohn U - 36059


SKIN AND EYE IRRITATION DATA AND REFERENCES:

ROUTE/
ORGANISM 		DOSE
EFFECT

 REFERENCE
N/R
 N/R N/R N/R


MUTATION DATA AND REFERENCES:

SYSTEM TEST ROUTE/
ORGANISM/
TISSUE 		DOSE REFERENCE
N/R N/R N/R N/R


REPRODUCTIVE EFFECTS DATA AND REFERENCES:

ROUTE/
ORGANISM 		DOSE
EFFECT

 REFERENCE
oral
mouse 		lowest published toxic dose: 887 mg/kg (84 day male) Reproductive: Effects on fertility: Male fertility index (e.g., # males impregnating females per # males exposed to fertile nonpregnant females) TOLED5 138,253,2003
oral
mouse 		lowest published toxic dose: 455 mg/kg (84 day male) Reproductive: Effects on fertility: Post- implantation mortality (e.g., dead and/or resorbed implants per total number of implants) TOLED5 138,253,2003
oral
rat 		lowest published toxic dose: 140 mg/kg (7 day prior to copulation) Reproductive: Effects on newborn: Delayed effects NETEEC 16,65,1994
oral
rat 		lowest published toxic dose: 100 mg/kg (6-10 day pregnant) Reproductive: Effects on fertility: Post- implantation mortality (e.g., dead and/or resorbed implants per total number of implants) TOXID9 44,229,2005
oral
rat 		lowest published toxic dose: 200 mg/kg (6-10 day pregnant) Reproductive: Maternal effects: Parturition

Reproductive: Specific developmental abnormalities: Eye, ear

Reproductive: Effects on newborn: Growth statistics (e.g., reduced weight gain) 		TOXID9 44,229,2005
oral
rat 		lowest published toxic dose: 190 mg/kg (1-19 day pregnant) Reproductive: Other effects to embryo or fetus

Reproductive: Specific developmental abnormalities: Musculoskeletal system

Reproductive: Other developmental abnormalities 		AECTCV 52,137,2007
oral
rat 		lowest published toxic dose: 570 mg/kg (1-19 day pregnant) Reproductive: Effects on fertility: Post- implantation mortality (e.g., dead and/or resorbed implants per total number of implants)

Reproductive: Effects on fertility: Litter size (e.g., # fetuses per litter; measured before birth)

Reproductive: Effects on embryo or fetus: Fetal death 		AECTCV 52,137,2007


TUMORIGENIC DATA AND REFERENCES:

ROUTE/
ORGANISM 		DOSE
EFFECT

 REFERENCE
N/R
 N/R N/R N/R


ACUTE TOXICITY DATA AND REFERENCES:

ROUTE/
ORGANISM 		DOSE
EFFECT

 REFERENCE
inhalation
rat 		lethal concentration (50 percent kill): 65 gm/m3/6 hour N/R ENTOX* -,99,2005
intramuscular
rat 		lowest published lethal dose: 250 mg/kg Peripheral Nerve and Sensation: Spastic paralysis with/without sensory change

Blood: Hemorrhage

Skin: After systemic exposure: Dermatitis, other 		VHTODE 41,355,1999
intraperitoneal
mouse 		lethal dose : 600 mg/kg N/R TXAPA9 93,319,1988
intraperitoneal
mouse 		lowest published toxic dose: 150 mg/kg Brain and Coverings: Other degenerative changes TXAPA9 93,319,1988
intraperitoneal
rat 		lethal dose (50 percent kill): 800 mg/kg N/R DEVEAA 33,66,1979
intraperitoneal
rat 		lowest published toxic dose: 40 mg/kg Nutritional and Gross Metabolic: Body temperature decrease LSPPAT 23,2509,1978
intraperitoneal
rat 		lowest published toxic dose: 80 mg/kg Biochemical: Metabolism (intermediary): Effect on inflammation or mediation of inflammation LSPPAT 23,2509,1978
intravenous
woman 		lowest published toxic dose: 0.1 mL/kg Behavioral: Coma

Cardiac: Change in rate

Lung, Thorax, or Respiration: Respiratory depression 		CTOXAO 43,113,2005
oral
child 		lowest published toxic dose: 0.625 mL/kg Behavioral: Somnolence (general depressed activity)

Behavioral: Change in psychophysiological tests

Cardiac: Change in rate 		HETOEA 22,95,2003
oral
duck 		lethal dose (50 percent kill): 7 gm/kg N/R PEMNDP 9,28,1991
oral
dog 		lethal dose (50 percent kill): 100 mg/kg N/R SPEADM 78-1,22,1978
oral
guinea pig 		lethal dose (50 percent kill): >400 mg/kg N/R DEVEAA 33,66,1979
oral
human 		lowest published toxic dose: 0.36 mL/kg Eye: Miosis (pupilliary constriction)

Cardiac: Change in rate

Lung, Thorax, or Respiration: Respiratory depression 		CTOXAO 44,19,2006
oral
man 		lowest published toxic dose: 3,571 mg/kg Behavioral: Ataxia

Behavioral: Coma

Cardiac: Pulse rate decreased with fall in BP 		HETOEA 16,600,1997
oral
man 		lowest published toxic dose: 0.286 mL/kg Gastrointestinal: Nausea or vomiting

Vascular: BP lowering not characterized in autonomic section

Behavioral: Coma 		BCLPT* 97,185,2005
oral
mouse 		lethal dose (50 percent kill): 1,085 mg/kg N/R MTPEEI (4),36,1995
oral
mouse 		lowest published toxic dose: 15 mg/kg Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: Phosphatases

Biochemical: Metabolism (intermediary): Other 		HETOEA 22,99,2003
oral
mouse 		lowest published toxic dose: 45 mg/kg Nutritional and Gross Metabolic: Changes in: Ca

Nutritional and Gross Metabolic: Changes in: P

Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: Transaminases 		HETOEA 22,99,2003
oral
quail 		lethal dose (50 percent kill): 788 mg/kg N/R FMCHA2 -,C20,1991
oral
rat 		lethal dose (50 percent kill): 400 mg/kg N/R 85KYAH 11,80,1989
oral
rat 		lowest published toxic dose: 20 mg/kg Nutritional and Gross Metabolic: Weight loss or decreased weight gain AECTCV 52,137,2007
oral
rat 		lowest published lethal dose: 40 mg/kg N/R AECTCV 52,137,2007
oral
rabbit 		lethal dose (50 percent kill): >100 mg/kg N/R DEVEAA 33,66,1979
oral
woman 		lowest published lethal dose: 200 µL/kg Brain and Coverings: Other degenerative changes

Cardiac: Other changes

Kidney, Ureter, and Bladder: Changes in tubules (including acute renal failure, acute tubular necrosis) 		AJEMEN 6,510,1988
skin
rat 		lethal dose (50 percent kill): >1,600 mg/kg N/R ENTOX* -,99,2005
skin
rabbit 		lethal dose (50 percent kill): >200 mg/kg N/R DEVEAA 33,66,1979
unreported route
rat 		lethal dose (50 percent kill): 600 mg/kg N/R JJTOEX 2,289,1989


OTHER MULTIPLE DOSE DATA AND REFERENCES:

ROUTE/
ORGANISM 		DOSE
EFFECT

 REFERENCE
intraperitoneal
rat 		lowest published toxic dose: 150 mg/kg/3 day- intermittent Behavioral: Alteration of operant conditioning FAATDF 9,131,1987
intraperitoneal
rat 		lowest published toxic dose: 30 mg/kg/3 day- intermittent Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: Other oxidoreductases FCTOD7 42,1785,2004
intraperitoneal
rat 		lowest published toxic dose: 75 mg/kg/3 day- intermittent Liver: Changes in liver weight

Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: Hepatic microsomal mixed oxidase (dealkylation, hydroxylation, etc.)

Related to Chronic Data: Changes in uterine weight 		FCTOD7 42,1785,2004
intraperitoneal
rat 		lowest published toxic dose: 150 mg/kg/3 day- intermittent Lung, Thorax, or Respiration: Changes in lung weight

Kidney, Ureter, and Bladder: Changes in kidney weight

Nutritional and Gross Metabolic: Weight loss or decreased weight gain 		FCTOD7 42,1785,2004
oral
mouse 		lowest published toxic dose: 455.28 mg/kg/12 week- continuous Behavioral: Fluid intake

Reproductive: Paternal effects: Prostate, seminal vesicle, Cowper's gland, accessory glands 		TOLED5 138,253,2003
oral
mouse 		lowest published toxic dose: 887.04 mg/kg/12 week- continuous Reproductive: Paternal effects: Spermatogenesis (including genetic material, sperm morphology, motility, and count)

Nutritional and Gross Metabolic: Weight loss or decreased weight gain

Related to Chronic Data: Changes in testicular weight 		TOLED5 138,253,2003
oral
mouse 		lowest published toxic dose: 1,712.76 mg/kg/12 week- continuous Reproductive: Paternal effects: Testes, epididymis, sperm duct TOLED5 138,253,2003
oral
rat 		lowest published toxic dose: 200 mg/kg/5 day- intermittent Endocrine: Change in LH TOXID9 44,229,2005
oral
rat 		lowest published toxic dose: 400 mg/kg/5 day- intermittent Biochemical: Metabolism (intermediary): Other

Biochemical: Neurotransmitters or modulators (putative): Dopamine in striatum

Biochemical: Neurotransmitters or modulators (putative): Dopamine at other sites 		TOXID9 90,304,2006
oral
rat 		lowest published toxic dose: 190 mg/kg/19 day- intermittent Lung, Thorax, or Respiration: Other changes

Gastrointestinal: Changes in structure or function of salivary glands

Nutritional and Gross Metabolic: Weight loss or decreased weight gain 		AECTCV 52,137,2007
oral
rat 		lowest published toxic dose: 570 mg/kg/19 day- intermittent Lung, Thorax, or Respiration: Other changes

Nutritional and Gross Metabolic: Weight loss or decreased weight gain

Related to Chronic Data: Death in the "MULTIPLE DOSE" data type field 		AECTCV 52,137,2007


REVIEWS:

ORGANIZATION STANDARD
REFERENCE
TOXICOLOGY REVIEW
TOLED5 142,207,2003
TOXICOLOGY REVIEW
MUTAEX 21,93,2006
TOXICOLOGY REVIEW
ENTOX* -,99,2005
TOXICOLOGY REVIEW
FEREAC 72,32570,2007
TOXICOLOGY REVIEW
FEREAC 72,53449,2007
TOXICOLOGY REVIEW
FEREAC 72,32570,2007
TOXICOLOGY REVIEW
FEREAC 72,53449,2007
TOXICOLOGY REVIEW
JTPAE7 19,1,2006


STANDARDS AND REGULATIONS:

ORGANIZATION STANDARD
REFERENCE
Environmental Protection Agency (EPA) Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC 54,7740,1989
Environmental Protection Agency (EPA) Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) 1998 STATUS OF PESTICIDES: RED Completed RBREV* -,85,1998


NIOSH DOCUMENTATION AND SURVEILLANCE:

ORGANIZATION STANDARD or SURVEY
REFERENCE
N/R N/R N/R


STATUS IN FEDERAL AGENCIES:

ORGANIZATION
REFERENCE
On EPA IRIS database


REFERENCES:

CODEN
REFERENCE
85KYAH "Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989
AECTCV Archives of Environmental Contamination and Toxicology. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 070944) V.1- 1973-
AJEMEN American Journal of Emergency Medicine. (WB Saunders, Philadelphia, PA) V.1- 1983-
BCLPT* Basic & clinical pharmacology & toxicology (Copenhagen, Denmark : Nordic Pharmacological Society Oxford, UK : Distributed by Blackwell Munksgaard) V.94- 2004-
CTOXAO Clinical Toxicology. (New York, NY) V.1-18, 1968-81. For publisher information, see JTCTDW.
DEVEAA Defense des Vegetaux. (Federation Nationale des Groupements de Protection des Cultures, 149, rue de Bercy, 75595 Paris Cedex, 12, France) V.1- 1947-
ENTOX* Encyclopedia of Toxicology: Reference Book, Elsevier, 2005
FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1-40, 1981-97. For publisher information, see TOSCF2
FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982-
FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936-
FMCHA2 Farm Chemicals Handbook. (Meister Pub., 37841 Euclid Ave., Willoughy, OH 44094)
HETOEA Human & Experimental Toxicology. (Macmillan Press Ltd., Brunel Road, Houndmills, Basingstoke, Hampshire, RG21 2XS, UK) V.9- 1990-
JJTOEX Japanese Journal of Toxicology. (Yakugyo Jihosha, Hokushin Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo, 101, Japan) V.1- 1988-
JTPAE7 Journal of Toxicologic Pathology. (Nihon Dokusei Byori Gakkai, editor, 3-25-8 Nishi- shinbashi, Minato-ku, Tokyo 105, Japan) V.1- 1988
LSPPAT Life Sciences, Part 1: Physiology and Pharmacology. (New York, NY) V.9-13, 1970-73. For publisher information, see LIFSAK.
MTPEEI Meditsina Truda i Promyshlennaya Ekologiya. Industrial Medicine and Ecology. (Mezhdunarodnaya Kniga, ul.B. Yakimanka, 39 117049 Moscow, Russia) No.1- 1993-
MUTAEX Mutagenesis. (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1986-
NETEEC Neurotoxicology and Teratology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.9- 1987-
PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968-
RBREV* Status of Pesticides in Registration, Reregistration, and Special Review (Rainbow Report), Special Review and Reregistration Division Office of Pesticide Programs U.S. Environmental Protection Agency, 401 M. Street, S.W., Washington, D.C. 20460, Spring 1998
SPEADM Special Publication of the Entomological Society of America. (4603 Calvert Rd., College Park, MD 20740)
TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977-
TOXID9 Toxicologist. (Soc. of Toxicology, Inc., 475 Wolf Ledge Parkway, Akron, OH 44311) V.1- 1981-
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959-
VHTODE Veterinary and Human Toxicology. (American College of Veterinary and Comparative Toxicology, Publication Office, Comparative Toxicology, Manhattan, KS 66506) V.19- 1977-

Used to control pear psylla on pears and tetranychid and eriophyid mites on fruit, etc.

RTECS Compound Description:
   Agricultural Chemical
   Reproductive Effector
   Human Data

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