1H-Pyrrole-3-carbonitrile, 4-bromo-2-(4-chlorophenyl)-5-trifluoromethyl
CAS No. 122454-29-9
 
 

Activity: Antifoulant, Fungicide (pyrrole)

CAS Name: 1H-Pyrrole-3-carbonitrile, 4-bromo-2-(4-chlorophenyl)-5-trifluoromethyl

Structure: not available

Note: This pesticide contains both bromine and fluorine; a combination that has the potential to produce severe adverse effects - particularly to the brain.

Adverse Effects:

• No toxicological data available. See above.

Regulatory Information
(only comprehensive for the US)
US EPA Registered: Pending
US EPA PC Code: 119093
Other Information:
Molecular Formula: C<12>H<5>BrClF<3>N<2>
Manufacturer: American Cyanamid Co.
Other Names:
AC 303268
AC 303,268
CL303, 268
Of special interest:
PAN Data 
Material Safety Data Sheet - 1997, American Cyanamid Co.
Parent chemical: Chlorfenapyr
See - http://www.fluorideaction.org/pesticides/chlorfenapyr-page.htm

Breakdown Products of
1H-Pyrrole-3-carbonitrile, 4-
bromo-2-(4-chlorophenyl)-5-trifluoromethyl
Chemical Name: US EPA PC Code: Ref:
2-Pyrroline-3-carbonitrile, 2-(p-chlorophenyl)-5-hydroxy-4-oxo-5- 619093 PAN
Pyrrole-2-carboxylic acid, 3-bromo-5-(p-chlorophenyl)-4-cyano- 619094 PAN
Pyrrole-2-carboxylic acid, 5-(p-chlorophenyl)-4-cyano-
(metabolite of AC 303, 268 )
619095 PAN
Chlorfenapyr is the first commercial pesticide to be derived from a class of microbially-produced compounds known as halogenated pyrroles.  Synthesized in 1988 from a naturally-produced chlorinated pyrrole, chlorfenapyr (AC 303,630 Technical: 4-bromo-2-(4-chlorophenyl)-1-(ethosymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile) is being used in at least 32 countries, including the United States.  Chlorfenapyr is a 'proinsecticide', i.e., it requires activation through metabolism. The parent compound is converted to a metabolite, which functions as an uncoupler of oxidative phosphorylation at mitochondria.The primary, and most toxic, metabolite is the N-dealkylated compound AC 303,268 (Fig. 1).Chlorfenapyr has low volatility and water solubility; is lipophilic; binds strongly to soil particles; and degrades slowly in soil (avg. half life of` 1 yr), sediment (avg. half life of 1.1 yr), and water (avg. half life of 0.8 yr).
Ref: Effects of Chlorfenapyr on Adult Birds, Patuxent Wildlife Research Center.
Compound AC 303,268


From Toxline at Toxnet

Source: DUKE, S. O., J. J. MENN AND J. R. PLIMMER (ED.). ACS SYMPOSIUM SERIES, 524. PEST CONTROL WITH ENHANCED ENVIRONMENTAL SAFETY; 203RD NATIONAL MEETING OF THE AMERICAN CHEMICAL SOCIETY, SAN FRANCISCO, CALIFORNIA, USA, APRIL 5-10, 1992. X+357P. AMERICAN CHEMICAL SOCIETY: WASHINGTON, DC, USA. ISBN 0-8412-2638-5.; 0 (0). 1993. 219-232.

Document Number: BIOSIS/93/30843

INSECTICIDAL PYRROLES

Authors: KUHN DG, ADDOR RW, DIEHL RE, FURCH JA, KAMHI VM, HENEGAR KE, KREMER KA, LOWEN GT, BLACK BC, ET AL

Abstract: RRM AC-303630 INSECTICIDE MITICIDE
Medical Subject Headings (MeSH):

CAS Registry Numbers:

122454-29-9 -
1H-Pyrrole-3-carbonitrile, 4-bromo-2-(4-chlorophenyl)-5-
trifluoromethyl


122453-73-0 - Chlorfenapyr: 1H-Pyrrole-3-carbonitrile, 4-bromo-2-(4-
chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-

105888-54-8 - Pyrroxamycin [Molecular Formula: C12-H6-Cl4-N2-O4]
52315-07-8 - Cypermethrin [Molecular Formula: C22-H19-Cl2-N-O3]
30560-19-1 - Acephate [Molecular Formula: C4-H10-N-O3-P-S]
16752-77-5 - Methomyl [Molecular Formula: C5-H10-N2-O2-S]
115-29-7 - Endosulfan [Molecular Formula: C9-H6-Cl6-O3-S]

62441-54-7 - several names: Hexafluoramin, Fentrifanil, Famaflur, Flufenamine, PP-199. [Molecular Formula: C14-H6-Cl-F6-N3-O4]

no information available as of January 2005
143464-11-3
122454-33-5
122454-31-3
122454-30-2
122453-72-9
122453-38-7
122452-96-4
122452-95-3
111237-02-6


US Federal Register
Date Published Docket Identification Number Details
Jan 6, 2005 OPP-2004-0294

Registration Applications for Pesticide Products Containing Active Ingredients Not Included in any Previously Registered Products.

Note the bromine + fluorine in the chemical formula. From previous pesticides with this combination we must be concerned about severe brain effects.

Note from EC: This chemical formula is similar to Chlorfenapyr (CAS No. 122453-73-0), which is one of the most reproductively toxic pesticides to avian species that EPA has evaluated. It is also a persistent compound in soil and sediment. Brain effects noted in rat and mice studies: spongiform myelopathy and/or vacuolation. In mice studies spongiform encephalopathy.

Product Name:
File Symbol:
Applicant:   Use: % Active Ingredient in product:

Econea Technical

43813-ET

William Goodwine, Janssen
Pharmaceutical, Inc.
,
Plant and Material Protection Division,
1125 Trenton-Harbourton Road,
Titusville, NJ 08560-0200
Antifoulant paint product. 93.2%.

Sigma Nexxium 20 Antifouling

11350-GL

Sigma Coatings USA BV,
Box 816,
Harvey, LA 70059
Antifoulant paint product. 3.4%

 

 
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