Trifloxystrobin
CAS No. 141517-21-7

 
 

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ACTIVITY: Fungicide (Strobin)

CAS Name: methyl (?E)-?-(methoxyimino)-2-[[[(E)-[1-[3-(trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]benzeneacetate

Structure:

Adverse Effects:

Body Weight Decrease
Bone
Endocrine: Pituitary
Endocrine:
Thymus
Eye
Kidney
Liver
Mesenteric Lymph Node
Pancreas
Spleen

Environmental Effects:

Very Highly Toxic to Freshwater and Estuarine/Marine Fish and Invertebrates

Trifloxystrobin's major metabolite, CGA-321113, is persistent and mobile and has a potential to leach into groundwater. It has been found in the soil profile at the 36 inch depth.

Regulatory Information
(only comprehensive for the US)
US EPA Registered: Yes 
US EPA PC Code: 129112 
California Chemical Code CFR 180.555  
Registered use in
(includes only a limited list of countries)

Australia, Canada, Germany, Hungary, New Zealand, South Africa, UK, US

Australia: Grape

Canada (As of March 2005): Apple, Crabapple, Grape, Grape (table), Grape (wine), Loquat mayhaw, Pear, Pear (Oriental), Quince, Wheat (Canada prairie), Wheat (durum), Wheat (hard red), Wheat (soft white), Wheat (spring), Wheat (winter) - Ornamentals, Turf

US Maximum Residue Levels permitted in food commodities
Permitted in or on 262 food commodities, including:
Almond, Apple, Aspirated Grain, Banana, Beet, Citrus dried pulp, Citrus oil, Corn, Egg,, Cattle, Sheep, Fruit (Pome), Grape, Goat, Hog, Horse, Milk, Nut tree group, Peanut, Pistachio, Potato, Poultry (fat, meat, and byproducts), Rice (grain, hulls and straw), Soybean (forage, hay, seed), Vegetable (Cucurbits & Fruiting), Wheat
  
UK Temporary MRL's

Applicable from: August 2003

Apple & Pear: 0.3 ppm
Winter wheat: 0.02 ppm

UK Import Tolerances

Citrus fruit: 0.3 ppm (as of 2002)
Cherry: 2.0 ppm (as of 2003)
Tomato: 1.0 ppm (as of 2003)
Soybean: 0.05 ppm (as of 2005)

Other Information
Molecular Formula: C20H19 F3 N2O4  
Entry Year: 1999 
Manufacturers: Bayer (Novartis/Syngenta) 
Other Names: Flint
Twist
Stratego
Sphere
Compass
Tega,
CGA 27920
2 F 279
CG-233
 
Manufacture site:

SWITZERLAND:
Novartis, Munchwilen

SWITZERLAND:
Bayer, Muttenz

Of special interest:
PAN Data 
Material Safety Data Sheets & Labels
July 19, 2005 - Canada. Reduced-Risk Update. Report: RR2005-02. Canada Pest Management Regulatory Agency (PMRA).
See excerpted list of fluorinated pesticides.
January 30, 2004 - Regulatory Note REG2004-03. Canada Pest Management Regulatory Agency. The active ingredient trifloxystrobin and associated end-use products (EPs) Compass 50 WG, Flint
50 WG and Stratego 250 EC (containing the fungicides trifloxystrobin and propiconazole) have been granted temporary registration under Section 17 of the Pest Control Products (PCP) Regulations. This Regulatory Note provides a summary of data reviewed and the rationale for the regulatory decision for these products. Also available at: http://www.hc-sc.gc.ca/pmra-arla/english/pdf/reg/reg2004-03-e.pdf
April 7, 2003 - Review report for the active substance trifloxystrobin. Trifloxystrobin. SANCO/4339/2000-Final. Finalised in the [European Commission] Standing Committee on the Food Chain and Animal Health at its meeting on 15 April 2003 in view of the inclusion of trifloxystrobin in Annex I of Directive 91/414/EEC. 
September 20, 1999 - US EPA FACT SHEET
Up to January 1, 2004: Congressional Request to allow this chemical to be Duty-Free up to Jan 1, 2004 (HR 3963 IH). 
March 28, 2002 - Residue Data Sheet. Australia National Regulatory Authority (NRA) for Agricultural & Veterinary Chemicals. 
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.  

Sept 2001 - June 2002 AUSTRALIA: Time-limited permit for use on banana trees in the Tully Banana Production Area.

December 7, 2000 - BAYER - Flint® fungicide aquired by Bayer. December 7, 2000, Press Release from Bayer Corporation. 
One of 8 fluorinated pesticides used to cultivate grapes in Australia. 
Flint 500 WG. Used on Grapes in Australia. Australian Wine Research Institute. 
In October 2000, Novartis Agribusiness announced the sale of its global trifloxystrobin business to Bayer for $760 million to satisfy anti-trust concerns over the planned merger with Zeneca’s agrochemical operation to form Syngenta (Zeneca marketed the rival strobilurin product, azoxystrobin, D0030L).  The sale included the entire trifloxystrobin (D0044) business including intellectual property rights, formulation technologies, trade marks, registration rights and production facilities in Muttenz, Switzerland.  Bayer agreed to retain the Muttenz workforce.  Bayer estimates that the Flint line has annual sales potential of €300 million and hopes to exploit its full ‘blockbuster’ potential within 5 years.  The sales potential will be further enhanced by the combinations to be developed with Bayer’s existing portfolio products and pipeline candidates. ... Crop protection business sales reached €2,708 million ($2,418 million) in 2001, up 10.3% on the previous year.  The acquisition of trifloxystrobin and sulcotrione made a significant contribution to this performance.
http://www.pjbpubs.com/agroprojects/weed_company.htm
Pesticide products - partial list 
April 2000 - Stratego® fungicide labeled for wheat by Don Hershman Extension Plant Pathologist. (Syngenta, Bayer, Novartis, Zeneca, Quadris.) University of Kentucky Wheat Science News. 
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: Trifloxystrobin 
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.  

US Federal Register

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

Date Published Docket Identification Number Details
September 19, 2007 EPA-HQ-OPP-2007-0539

Bayer CropScience. Pesticide tolerance. FINAL RULE. This regulation establishes a tolerance for combined residues of Trifloxystrobin and the acid metabolite CGA-321113, at higher levels than requested by Bayer, in or on

-- Grass, forage at 12 ppm (Bayer requested 10.0 ppm)
-- Grass, hay at 17 ppm (Bayer requested 14.0 ppm)

April 11, 2007: Human Health Risk Assessment for Section 3 Registration for the Proposed Uses on Grasses Grown for Seed.

Based upon review of the data supporting the petition, EPA has modified the tolerances proposed for grass, forage and grass, hay. The appropriate tolerances for grass forage and hay were calculated to be 12 and 17 ppm, respectively. Although residue data were also provided for grass straw and seed screenings, tolerances are not required on these commodities as the Agency no longer considers them to be significant livestock feedstuffs. The recommended tolerance levels for grass forage and hay were determined considering recent Agency Guidance (Guidance for Setting Pesticide Tolerances Based on Field Trial Data).

Conclusion. EPA has determined that reliable data show that it would be safe for infants and children to reduce the FQPA safety factor to 1X. That decision is based on the following findings:
i. The toxicity database for Trifloxystrobin is complete except for an acute neurotoxicity study which is classified as unacceptable. The toxicity database contains developmental toxicity studies in two species (rats and rabbits) and a 2-generation reproduction study in rats which are adequate to assess pre and/or post natal susceptibility to infants and children. Although the available, submitted acute neurotoxicity study was found to be unacceptable, based on a weight-of- the evidence review of the available data, the lack of this study does not impact the Agency's ability to make an FQPA safety factor decision. Given that there was no evidence of neurotoxicity in this study at the Limit Dose nor in the other subchronic and chronic studies in the database there is not an uncertainty concerning neurotoxic effects and EPA has reliable data to show that removal of the FQPA safety factor is safe for children. Additionally, these data demonstrate that a developmental neurotoxicity study is not required for this pesticide.

August 1, 2007 EPA-HQ-OPP-2007-0539

Bayer CropScience. Pesticide Petition PP 6F7024. Proposal to establish a tolerance for residues of the fungicide trifloxystrobin in or on food commodities

-- grass, forage at 10.0 ppm
-- grass, hay at 14.0 ppm.

A practical analytical methodology for detecting and measuring levels of trifloxystrobin in or on raw agricultural commodities has been submitted. The limit of detection (LOD) for each analyte of this method is 0.08 ng injected, and the limit of quantitation (LOQ) is 0.02 ppm. The method is based on crop specific cleanup procedures and determination by gas chromatography with nitrogen-phosphorus detection.

September 22, 2006 EPA-HQ-OPP-2005-0299 Bayer CropScience. Pesticide Tolerance. FINAL RULE.
in or on
-- soybean, forage at 10.0 ppm
-- soybean, hay at 25.0 ppm
-- soybean, seed at 0.08 ppm.
September 13, 2006 EPA-HQ-OPP-2006-0730

IR-4. Pesticide petition: PP 6E7088.
Proposing the establishment of new tolerances in or on
-- asparagus at 0.07 ppm
-- papaya at 0.4 ppm
-- sapote, black at 0.4 ppm
-- canistel at 0.4 ppm
-- sapote, mamey at 0.4 ppm
-- mango at 0.4 ppm
-- sapodilla at 0.4 ppm
-- star apple at 0.4 ppm
-- radish, tops at 20 ppm

-- vegetable, root, except sugar beet, subgroup 1B at 0.2 ppm

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

June 28, 2006 EPA-HQ-OPP-2006-0084

Notice of Receipt of Requests to Voluntarily Cancel Certain Pesticide Registrations.

EPA Registration No. Product Name Registrant
000264 WA-01-003 Stratego Fungicide Bayer Cropscience LP
2 T.W. Alexander Drive
Research Triangle Park, NC 27709.
March 29, 2006 EPA-HQ-OPP-2005-0299 Bayer CropScience and IR-4. Pesticide Tolerance. FINAL RULE.
This regulation establishes a tolerance for combined residues of trifloxystrobin and the free form of its acid metabolite CGA-321113 ((E,E)-methoxyimino-[2-[1-(3-trifluoromethylphenyl)-ethylideneaminooxymethyl]-
phenyl]acetic acid) pesticide petition (PP 4F6892) in or on
Commodity
Parts per million
Registrant Pesticide Petition
Barley, grain
0.05
IR-4 PP 3E6769
Barley, hay
0.3
IR-4 PP 3E6769
Barley, straw
5.0
IR-4 PP 3E6769
Corn, sweet, cannery waste
0.6
BAYER PP 4F6892
Corn, sweet, forage
0.6
BAYER PP 4F6892
Corn, sweet, kernel plus cob with husks removed
0.04
BAYER PP 4F6892
Corn, sweet, stover
0.25
BAYER PP 4F6892
Oat, forage
0.3
IR-4 PP 3E6769
Oat, grain
0.05
IR-4 PP 3E6769
Oat, hay
0.3
IR-4 PP 3E6769
Oat, straw
5.0
IR-4 PP 3E6769

• Specific information on the studies received and the nature of the toxic effects caused by trifloxystrobin and CGA-321113 as well as the no-observed adverse effect level (NOAEL) and the lowest observed adverse effect level (LOAEL) from the toxicity studies can be found in the Federal Register of May 22, 2002

Effects cited only from rat studies: decreases in body weight, body weight gains, reduced food consumption and histopathological lesions in the liver, kidneys and spleen

Cancer. EPA determined that trifloxystrobin should be classified as a ``Not Likely Human Carcinogen.'' Due to the classification, no cancer exposure assessment was performed.

Conclusion. EPA determined that the 10X SF to protect infants and children should be reduced to 1X. The FQPA, SF is reduced because ...
iii. EPA determined that a developmental neurotoxicity study in rats is not required;
iv. Although an acute neurotoxicity study is required (the submitted study was unacceptable), the lack of an acute neurotoxicity study does not impact EPA's ability to make an FQPA safety factor decision because upgrading the study would not result in a lower NOAEL than what is present for the acute RfD ...

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

 
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