Bifenthrin
CAS Nos. 82657-04-3 (Cis) and 83322-02-5 (Trans)
 
 

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Adverse Effects
Abstracts

ACTIVITY: Insecticide, Acaricide (pyrethroid)

CAS Name: (2-methyl[1,1?-biphenyl]-3-yl)methyl 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate

Structure:

Adverse Effects:

Ataxia
Bladder
Body Weight Decrease
Cancer: Possible Human Carcinogen URINARY BLADDER, LIVER,
LUNG
Endocrine: Ovary/Estrus

Endocrine: Suspected Disruptor
Endocrine: Thyroid
Liver
Lung
Tremors/Convulsions
Tumor Promoter

Environmental Effects:

Very Highly Toxic to Fish and Zooplankton
Very persisten in aquatic sediment
Groundwater pollutant

Regulatory Information
(only comprehensive for the US)
US EPA Registered: Yes
US EPA PC Code: 128825 
California Chemical Code 2300
US Tolerances: 180.442
FDA LMS Code: 930
US EPA Permit Date
and Registrant:
1985, FMC
Registered use in
(includes only a limited list of countries)

Australia, Hungary, New Zealand, Pakistan, Portugal, South Africa, Tanzania, Uganda, UK, US

EU:
Tea

Japan's Maximum Residue Levels (MRLs)

Partial List:
Apple • Artichoke • Asparagus • Banana • Beans • Broccoli • Brussels sprouts • • Cabbage • Cauliflower • Cherry • Corn • Cotton seeds • Cucumber (including Gherkin) • Eggplant • Grape • Grapefruit • Hop • Japanese plum (including Prunes) • Lemon • Lime • Loquat • Melons • NATSUDAIDAI (whole) • Orange (including Navel) • Other berries • Other Citrus fruits • Other Vegetables • Peach • Pear • Potato • Quince • Rape seeds • Strawberry • Sugar beet • Tea • Tomato • UNSHU orange • Watermelon

-- Note high levels - 25 ppm - for Tea (Green, Black, Oolong, Wulung)

US Maximum Residue Levels permitted in food commodities

As of Feb 11, 2005, Permitted in or on 198 food commodities including:
Artichoke, Brassica, Cabbage, Caneberry, Cattle, Citrus Fruit & Oil, Corn, Cotton, Egg, Eggplant, Goat, Grape, Hogs, Horse, Lettuce, Milk, Peanut meat (hulls removed), Pepper (bell and non-bell), Poultry, Potato, Rapeseed, Sheep, Strawberry, Sweet Potato, Legumes, Cattle, Goat, Hog, Horse, Poultry, Sheep

Also, a tolerance of 0.05 ppm In or on all food/feed items (other than those covered by a higher tolerance as a result of use on growing crops) in food/feed handling establishments, such as restaurants, cafeterias, supermarkets, bakeries, breweries, dairies, meat slaughtering and packing plants, and canneries, feed handling establishments including feed manufacturing and processing establishments.

Other Information
Molecular Formula: C23H22Cl F3 O2 
Manufacturers: FMC   
Other Names: Capture, Biphenate,
Biphenthrin, Bifenthrine,
Biflex, Biphentrin
Brigade, Capture, DeterMite,
FMC 54800, Talstar
Manufacture site:

US
FMC, Baltimore,
Maryland 21226

Of special interest:
PAN Bad Actor (Develomental or Reproductive Toxin and Suspected Endocrine Disruptor)
Material Safety Data Sheets & Labels
Oct 26, 2005 - Pyrethroid pesticides found at toxic levels in California urban streams. By Robert Sanders.
A group of commonly used pesticides recently found at toxic levels in stream sediments in many agricultural areas around California is also a problem in urban streams, according to a new study by researchers from the University of California, Berkeley, Southern Illinois University and the Central Valley Regional Water Quality Control Board...
Bifenthrin, the pyrethroid that contributed most to the toxicity measured in the study, is available widely and sometimes mixed with fertilizer to spread as granules over lawns... Weston said that the most toxic of the pyrethroids - all of which are identified by the suffix -thrin - was bifenthrin, which could have gotten into the streams as runoff from homes treated by professional pest-control companies for pest such as ants, or from lawns treated with pesticides or popular fertilizer/pesticide combinations... Weston and his colleagues reported their findings in the Oct. 19 online issue of Environmental Science & Technology (ES&T), a publication of the American Chemical Society. The article will appear in the Dec. 1 print edition.
•• See also Science News: ... bifenthrin, was found at levels about 15 times higher than those reported in areas of California with intensive agriculture...
May 23, 2005 - Court Issues Preliminary Injunction in FMC Label Infringement Case Against CSI. PCT Online.

Bifenthrin is used as a preconstruction termite barrier in Austrailia. See:
DeterMite - a preconstruction timber termiticide
Weyerhaeuser Material Safety Data Sheet: H2-F (Bifenthrin) Treated TJI Joist

Talstar termiticide. FMC Material Safety Data Sheet for Talstar (2004)
2004-2006 - US EPA CHEERS study in Jacksonville, Duval County, Florida. This 2-year study of children's exposure to selected pesticides and chemicals has ignited enormous controversy. Bifenthrin was one of 16 pesticides selected to be monitored in children (ages 0-3 years). See FAN's updates on this study.
March 14, 2005: Upswing in Lesser Used, but More Potent Pesticides in California's Central Valley.
University of California-Berkeley researchers have conducted a study to determine the harmful effects of pyrethroid pesticides on aquatic organisms through sediment residues. What they have found is a trend toward using newer compounds that can be more toxic to aquatic life. The team of researchers studied six pyrethroids in three sediments taken from California’s Central Valley, where two-thirds of the state’s cropland is found. Study results showed acute toxicity and growth impairment in the amphipod Hyalella azteca, a sensitive test species. Animal biomass was roughly 38% below that of the control group when exposed to pyrethroid levels that were one-third to one-half of the lethal concentration. Except for permethrin, most pyrethroids would be acutely toxic to H. azteca at concentrations only slightly above detection limits. The six compounds tested in order of decreasing toxicity were bifenthrin, lambda-cyhalothrin, deltamethrin, esfenvalerate, cyfluthrin and permethrin.
To read the entire study, click here: http://www.allenpress.com/pdf/entc_24_414_966_972.pdf
2003 - Australia. Health Based Investigation Level for Bifenthrin in Soil, by Sarah Taylor and Peter Di Marco, Department of Health, Western Australia.
US MAP of pesticide use based on 1991-1995 data 
US EPA Maximum residue tolerance levels in 116 food commodities as of September 25, 2003.
TOXNET profile from Hazardous Substances Data Bank
List of Bifenthrin insecticide products in the US 
September 2001 - DRAFT TOXICOLOGICAL PROFILE FOR PYRETHRINS AND PYRETHROIDS. U.S. DEPARTMENT OF HEALTH AND HUMAN SERVICES. The fluorinated pyrethroids discussed in this report are: Bifenthrin (Type I), Cyfluthrin (Type II) , Cyhalothrin (Type II), Flucythrinate (Type II) , Flumethrin (Type II), Fluvalinate (Type II), Tefluthrin (Type I). Public Health Service Agency for Toxic Substances and Disease Registry. http://www.atsdr.cdc.gov/toxprofiles/tp155.pdf
Abstracts
2000 Toxic Release Inventory. Brief Summary.
January 25, 1999 - Sediment Toxicity and Fate of Synthetic Pyrethroids. The synthetic pyrethroids were conditionally registered beginning in 1984 for use on cotton and later for use on other major crops including corn, soybeans, and sugarcane. Currently, EPA is assessing risks to non-target organisms for ten synthetic pyrethroids: bifenthrin, cyfluthrin, cypermethrin, deltamethrin, fenpropathrin, fenvalerate, cyhalothrin, tefluthrin, tralomethrin, and permethrin. Each of these synthetic pyrethroids are conditionally registered for use on cotton, with the exception of tefluthrin, which is conditionally registered for use on corn. Each of these chemicals is highly lipophilic and in aquatic environments tend to strongly adsorb to sediments. Environmental Fate and Effects Division Office of Pesticide Programs U.S. Environmental Protection Agency Washington, D.C.
Note: organofluorine pesticides highlighted in red.
November 1995 - Pesticide Fact Sheet - U.S. Department of Agriculture
1999 - Environmental Fate of Bifenthrin - California Environmental Protection Agency. Also at: http://www.cdpr.ca.gov/docs/empm/pubs/fatememo/bifentn.pdf
June 2002 -In Australia when Bifenthrin is used "As an insecticide and acaricide on ornamentals - Seed Lucerne treatment" no maximum residue levels are required. Ref: June 2002. Table 5. Uses of substances where maximum residue limits are not necessary. Australian National Registration Authority for Agricultural Veterinary Chemicals. The MRL Standard. Maximum residue limits in food and animal feedstuff. http://www.nra.gov.au/residues/mrl5.pdf
April 2002 - Beer in the UK: 23 organofluorine pesticides approved for use on malting barley. Published by the British Beer and Pubs Association and Brewing Research International.
2000 - "P" is for Poison. Update on Pesticide Use in California Schools, by TM Olle. A report by Californians for Pesticide Reform. Also available at: http://www.calpirg.org/healthyschools/PDFs/healthyschools.pdf
The fluorinated pesticides cited in this report are:
Benefin (Benfluralin), Bifenthrin, Bromethalin, Cyfluthrin, Fipronil, Fluazifop-butyl, Hydramethylnon, Lambda-cyhalothrin, Sulfuryl fluoride (Vikane), Trifluralin
October 1998 - Structural Pest Management pesticides. FAN's compilation of information cited on fluorine and organofluorine pesticides published in General Pest Management, Category 7A. A Guide for Commercial Applicators. Prepared by: Carolyn Randall, MSU Pesticide Education Program. Published by MSU Pesticide Education (Michigan State University). MSU manual number: E-2048.
1999 - Pesticide Information Profile - Cornell Extoxnet Profile
August 2001 - IR-4 New Products/Transitional Solution List This list contains brief descriptions of numerous new pest control materials that have been introduced over the last several years. Additionally, it contains information on some "older" crop protection chemicals that are believed to have room for new uses. This List includes: Bifenthrin
Online as of Dec 2, 2001 - Japan - Listed as a "Deleterious Substance" under the "Poisonous and and Deleterious Substances Control Law" by the National Institute of Health Sciences in Japan.
October 2001 - Glossary of Pesticide Chemicals. A listing of pesticides subject to analysis of residues in foods and feeds by the US Food and Drug Administration.
April 2000 - Food and Drug Administration Pesticide Residue Monitoring. Table 3. Pesticides detectable and found by methods used in 1999 regulatory monitoring.

Rationale for US EPA to add Bifenthrin to the Toxic Release Inventory

Tremors or head and forelimb twitching were noted in dogs, rats and rabbits exposed to various doses. NOEL values based on the appearance of tremors (often transient) ranged from 1 to 2.67 mg/kg/day. The oral RfD for bifenthrin was based on a 1 year beagle dog feeding study, in which the LOEL, based on tremors observed during weeks 15 to 29, was 3.0 mg/ kg/day and the NOEL was 1.5 mg/kg/day. The RfD based on this NOEL was 0.015 mg/kg/day. In a rat teratology study, an increased incidence of hydroureter (without hydronephrosis) was noted in fetuses at 2 mg/kg/day (LOEL). The NOEL was 1 mg/kg/day. EPA believes that there is sufficient evidence for listing bifenthrin on EPCRA section 313 pursuant to EPCRA section 313(d)(2)(B) based on the available neurological and developmental toxicity data. Aquatic acute toxicity values for bifenthrin include a bluegill 96- hour LC 50 of 0.35 ppb, a rainbow trout 96-hour LC 50 of 0.15 ppb, a sheepshead minnow LC 50 of 17.5 ppb, and a daphnid 48-hour EC 50 of 1.6 ppb. EPA believes that there is sufficient evidence for listing bifenthrin on EPCRA section 313 pursuant to EPCRA section 313(d)(2)(C) based on the available environmental toxicity data.

Ref: USEPA/OPP. Support Document for the Addition of Chemicals from Federal Insecticide, Fungicide, Rodenticide Act (FIFRA) Active Ingredients to EPCRA Section 313. U. S. Environmental Protection Agency, Washington, DC (1993). As cited by US EPA in: Federal Register: January 12, 1994. Part IV. 40 CFR Part 372. Addition of Certain Chemicals; Toxic Chemical Release Reporting; Community Right-to-Know; Proposed Rule.


Table D2: Details of Residues Exceeding non-harmonised MRLs,
including national MRLs

Surveillance sampling
Reporting country: Germany
Year of sampling: 2003
http://www.bvl.bund.de/lebensmittel/dateien/eg03-642d2_v2.pdf
Pesticide Food item Point of sampling (*) Country of origin Residue in mg/kg national MRL (mg/kg) Follow-up (**)
bifenthrin Lettuce W NL 0.12 0.05 A
bifenthrin Papaya R EC 0.12 0.05 - 
bifenthrin Papaya R EC 0.15 0.05 - 
bifenthrin Pears O TR 0.08 0.05 - 
bifenthrin Pears O TR 0.08 0.05 - 
bifenthrin Peppers R ES 0.18 0.05 - 
bifenthrin Strawberries R BE 0.06 0.05 - 
bifenthrin Strawberries O FR 0.07 0.05 - 
bifenthrin Table Grape R IT 0.052 0.05 - 
bifenthrin Table Grape R IT 0.068 0.05 - 
bifenthrin Table Grape O IT 0.069 0.05 - 
bifenthrin Table Grape O QU 0.06 0.05 - 

(*) Point of sampling in distribution: F = farmgate, R = retail, W = wholesale, O = other

(**) A: Administrative consequences have followed, e.g. prohibiting for sale, prosecutions, the levying of penalties or fines

These explanatory notes are cited at http://www.bvl.bund.de/lebensmittel/dateien/eg03-642d1_v2.pdf


Table 6-1. Trends of National Pyrethroid Use

Ref: September 2001. Draft Toxicological Profile for Pyrethrins and Pyrethroids. US Department of Health and Human Services. Public Health Service Agency for Toxic Substances and Disease Registry. Organofluorine pyrethroids discussed in the Profile: Bifenthrin (Type 1), Cyfluthrin (Type 2), Cyhalothrin (Type 2), Flucythrinate (Type 2), Flumethrin (Type 2), Fluvalinate (Type 2), Tefluthrin (Type 1).

Note from EC: The following 4 organofluorine pesticides were included in a list of 11 pesticides.

Pyrethroid Amounts applied
(pounds)
1992
Amounts applied
(pounds)
1997
Percent change
Bifenthrin 116,716 110,246 -5
Cyfluthrin 124,360 177,782 +43
lambda Cyhalothrin 205,329 321,284 +57
Tefluthrin 238,429 576,865 +142

June 14, 2001 - Implementation of the Community Strategy for Endocrine Disruptors - a range of substances suspected of interfering with the hormone systems of humans and wildlife. Communication from the Commission to the Council and the European Parliament. Commission of the European Communities, Brussels COM (2001) 262 final.
-More information available at:
http://europa.eu.int/comm/environment/docum/01262_en.htm

This document presents a "priority list of substances for further evaluation of their role in endocrine disruption. During 2000, a candidate list of 553 man-made substances and 9 synthetic/natural hormones has been identified." Organofluorine pesticides in this list include:

Substances included on the Endocrine Disruptor Liist CAS No. Substances included on the Endocrine Disruptor Liist CAS No.
Bifenthrin 82657-04-3  Flutriafol 76674-21-0
Cyhalothrin (@Karate) 91465-08-6 Fluvalinate 69409-94-5
Diflubenzuron 35367-38-5 Prodiamine 29091-21-2
Epoxiconazole - Stannane, tributylfluoro [Tributyltin fluoride] 1983-10-4
Fipronil - Thiazopyr -
Fluazifop-butyl 69806-50-4 Trifluralin -


US Federal Register

•• Note: Due to length, the following is a partial list. Click here to see full list of FR entries.

Published Date Docket Identification Number Details
October 24, 2007 EPA-HQ-OPP-2007-0471

IR-4. Pesticide tolerance. FINAL RULE. Documents available with this Final Rule:

• Bifenthrin: Risk Assessment. Docket # EPA-HQ-OPP-2007-0471-0008
• Bifenthrin: Dietary Review. Docket # EPA-HQ-OPP-2007-0471-0007
• Bifenthrin: BEAD. Review Docket # EPA-HQ-OPP-2007-0471-0006

Commodity

PPM

FINAL RULE

PPM

Requested

Pesticide Petition Number
Beet, garden, roots

0.45 same PP 6E7126
Beet, garden, tops
15 same PP 6E7126
Grain, aspirated fractions 70 None  
Groundcherry 0.5 None  
Mayhaw
1.4 same PP 6E7125
Peanut 0.05 same PP 6E7127
Pepino 0.5 None  
Pistachio 0.05 same PP 6E7127
Radish, tops 4.5 None  
Soybean, hulls
0.50 None  
Soybean, refined oil
0.30 None  
Soybean, seed 0.2 0.2
for "Soybean"
PP 6E7128
Vegetable, root, subgroup 1B except sugar beet and garden beet
This subgroup includes 19 commodities: beet, garden • burdock, edible • carrot • carrot culls • celeriac • chervil, turnip rooted • chicory root • ginseng • horseradish • parsley, turnip rooted • parsnip • radish • radish, oriental • rutabaga • salsify • salsify, black • salsify, spanish • skirret • turnip
0.10 0.07 PP 6E7126

Cancer. Bifenthrin was classified as a group ``C'' (possible human carcinogen). The Agency concluded that the chronic risk and exposure assessment, making use of the cPAD, to be protective of any potential carcinogenic risk. Therefore, no separate exposure assessment was conducted pertaining to cancer risk.

Note on Petiton for Vegetable, fruiting, group 8. Tolerances are established for residues of bifenthrin per se at 0.05 ppm in/on eggplant, at 0.15 ppm in/on tomato, and at 0.5 ppm in/on bell and non-bell pepper. EPA has determined that a fruiting vegetables crop group tolerance for residues of bifenthrin per se is not appropriate for the following reasons:
Maximum residues in eggplant are more than a factor of five lower than the tolerance for tomatoes and the use pattern for tomato and tomatillo are different from the other members of the crop group in terms of the PHI, maximum seasonal use rate, number of applications, and interval between applications. However, EPA is establishing tolerances for residues in/on groundcherry and pepino at 0.50 ppm based on the 0.5 ppm tolerance for bell and non-bell pepper. As 40 CFR 180.1 indicates that a tolerance for residues in/on tomato applies to tomatillo, a tolerance for residues in/on tomatillo is not required.

From July 25, 2007, Health Risk Assessment;

• Page 3. Bifenthrin is a neurotoxic insecticide acting through direct contact and ingestion, having a slight repellent effect. The primary biological effects of bifenthrin and other pyrethroids on insects and vertebrates are inhibition of the voltage-gated Ca 2+ channels coupled with a stimulatory effect on the voltage-gated Na+ channels. All pyrethroids act as axonic poisons, affecting both the peripheral and central nervous systems, and share similar modes of action. Pyrethroids, including bifenthrin, stimulate repetitive action in the nervous system by binding to voltage-gated sodium channels, prolonging the sodium ion permeability during the excitatory phase of the action potential. This action leads to spontaneous depolarizations, augmented neurotransmitter secretion rate and neuromuscular block, which ultimately results in paralysis of the insect.

• Page 4. Bifenthrin produces characteristic pyrethroid neurotoxicity. Tremors have been observed in developmental toxicity studies in the rat and rabbit, a 2-generation rat reproduction toxicity study, subchronic toxicity studies in the rat and dog, acute and subchronic neurotoxicity rat studies, a 21-day toxicity dermal rat study, chronic oral toxicity studies in the rat and dog, and a mouse oncogenicity study. The subchronic and chronic oral toxicity studies in dogs and rats demonstrate neurotoxicological responses of similar magnitude. Staggered gait and exaggerated hindlimb flexion were noted in a 21-day dermal toxicity study in the rat. The neurotoxicity of bifenthrin has been supported by the results of acute and subchronic neurotoxicity studies in the rat. Functional observation battery (FOB) findings were observed in these neurotoxicity studies. FOB findings consisted of tremors, abnormal posture, splayed hindlimbs, staggered gait, altered activity, altered landing foot-splay, twitching, uncoordinated movement/ataxia, and convulsions.

• Page 4. A developmental neurotoxicity (DNT) study on bifenthrin with rats has been submitted. In this study, maternal and offspring toxicity was observed at the same dose levels. The maternal toxicity was primarily manifested as tremors, clonic convulsions, and increased grooming counts. The offspring toxicity was manifested as increased grooming counts. This study does not show any evidence of increased susceptibility of offspring following exposure to bifenthrin.

• Pages 13-14. The CPRC (1992) has characterized bifenthrin as Category C (possible human carcinogen) and recommended that for the purpose of risk characterization, the RfD approach should be used for quantification of human cancer risk. This decision was based in part on the statistically significant increased trend for hemangiopericytomas in the urinary bladders’ of Swiss Webster mice. The incidence of these lesions was double at the highest dose tested (HDT; 600 ppm) as compared to controls. The male mice also had significant dose-related trends with respect to hepatocellular carcinomas and combined hepatocellular adenomas and carcinomas, and increased incidences of bronchioalveolar adenomas and adenocarcinomas of the lung in females at 50, 200 and 600 ppm (but not 500 ppm) relative to their controls.

• Page 24. In a 2-generation study (MRID 00157225), liquified bifenthrin (88.35% ai) mixed with acetone was administered in the diet to TAC(SD)fBR rats (25/sex/dose) at dose levels of 0, 30, 60, or 100 ppm as FMC 54800 technical (approximately equivalent to 0, 1.5, 3.0 and 5.0 mg/kg/day)... In the high-dose P generation females, there was a statistically significant increase in absolute and relative brain weights... In the 100 ppm group F1b female progeny, absolute adrenal and heart weights were statistically elevated compared to control values. Significantly elevated absolute ovary and ovary/brain weights were also observed in these animals.

•• Note: Due to length, the above is a partial list. Click here to see full list of FR entries.


 
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