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% |
|
|