Tetraconazole
CAS No. 112281-77-3

 
 

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ACTIVITY: Fungicide (azole)

CAS Name: 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]-1H-1,2,4-triazole

Structure:

Adverse Effects:

Amyloidosis
Blood
Body Weight Decrease

Bone

Brain
Cancer: Likely to be Carcinogenic to Humans - LIVER
Cholesterol
Endocrine: Ovary
Endocrine: Pituitary
Endocrine: Prostate
Endocrine:
Testicular

Endocrine: Thymus
Endocrine: Thyroid
Endocrine: Uterus
Endocrine: Vaginal
Kidney
Liver
Lung
Reproductive/Developmental

Environmental:

Persistent in soil and water sediment
Moderately toxic to birds
Highly toxic to fish, aquatic invertebrates, algae/aquatic plants and sediment dwelling organisms
Hazardous to bees
Moderately toxic to earthworms

Regulatory Information
(only comprehensive for the US)

US EPA Registered: Yes 
US EPA PC Code: 120603 
US Tolerances: CFR 180.557  
Registered use in
(includes only a limited list of countries)

Brazil, Greece, Hungary, Itally, Japan, Portugal, South Africa, Spain, Taiwan, UK, US 
Japan's Maximum Residue Levels (MRLs) Apple, Apricot, Artichoke,
Barley, Cherry, Cucumber,
Grape, Loquat, Makuwauri,
Melons, Nectarine,
Oriental pickling melon,
Other cereal grains,
Other cucurbitaceous vegs,
Peach, Pear, Plum,
Pumpkin (inc Squash),
Quince, Strawberry,
Sugar beet, Tomato,
Watermelon, Tea, Wheat
 
US Maximum Residue Levels permitted in food commodities
Permitted in or on 10 food commodities, including:
Cattle, Milk, Sugarbeets,
Sugarbeet-related commodities
 
Other Information
Molecular Formula: C13H11Cl2 F4 N3O 
Entry Year: 1993 
Manufacturers: Isagro-Ricerca 
Other Names: Arpege
Buongiorno
Domark
Eminent
Hokugard
Lospel
M 14360
TMF-931
 
Of special interest:
PAN BAD ACTOR - Carcinogen 

January 26, 2007 - Tetraconazole: Human-Health Risk Assessment for Proposed Uses on Soybean, Sugar Beet, Peanut, Pecan, and Turf. Federal Register Docket #: EPA-HQ-OPP-2006-0576-0010. - 105 pages.

July 2007 - Summary of toxicology data. California EPA, Department of Pesticide Regulation, Medical Toxicology Branch.

August 2005 - Evaluation of Tetraconazole in the product Domark 40ME Fungicide. Australian Pesticides and Veterinary Medicines Authority.

Detectable residues are likely to occur in table grapes. There are no import tolerances for tetraconazole residues in/on table grapes in the major export markets (ie Hong Kong, Singapore and Malaysia). In contrast to the wine industry, the table grape industry does not have the same QA programs in place to manage chemical residues in exported produce. The table grape industry should be made aware that residues of tetraconazole may present a risk to Australia’s export trade in this commodity. (page 14)

April 2005 - EPA Pesticide Fact Sheet: Tetraconazole.

The end-use product, Eminent 125SL, contains 11.6% tetraconazole by weight and is a liquid fungicide for control of Cercospora leafspot and powdery mildew on sugar beets. The proposed application method is ground and aerial application as a foliar spray or by chemigation. The applications must by alternated with non-triazole fungicides. Applications should begin when disease conditions are favorable and be repeated at 21-28 day intervals. A maximum of two applications per growing season may be made using 13 fluid ounces of a 1pound per gallon product per acre. The preharvest interval is 14 days. The product is for agricultural use only. The pesticide's use is proposed in seven U.S. states: CO, MI, MN, MT, ND, NE, and WY.

April 27, 2005 - U.S. Congressman David Price (D-NC) introduced a bill "to suspend temporarily the duty on Tetraconazole" up to December 31, 2009. The bill was referred to the House Committee on Ways and Means.
March 24, 2005 - Tetraconazole, which will be sold as Domark in the United States ... contains the triazole class of chemistry that is currently used on 75 percent of all soybean acres treated in Brazil...
.......Valent recently acquired the rights to sell Domark fungicide in the U.S. soybean market from Isagro SpA...
.......Domark is now available for use in Alabama, Arkansas, Delaware, Georgia, Illinois, Indiana, Iowa, Kansas, Kentucky, Louisiana, Maryland, Michigan, Minnesota, Mississippi, Missouri, Nebraska, New York, North Carolina, North Dakota, Ohio, Oklahoma, Pennsylvania, South Carolina, South Dakota, Texas, Virginia, West Virginia and Wisconsin for the control of Asian soybean rust under a Section 18.
Delta Farm Press.
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.  
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: Tetraconazole  
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.  

Hazard Characterization (Page 13)
1,2,4-triazole (free triazole) is a metabolite common to a number of triazole-derivative pesticides, and is found in both mammalian (rat) and plant metabolism studies. Although for most pesticides, mammals convert only a small proportion to free triazole (less than 25%), two compounds (tetraconazole and flusilazole) demonstrate relatively high conversion (68-77%) in rat metabolism studies. ...(Ref:
Human Health Aggregate Risk Assessment for Triazole-derivative Fungicide Compounds (1,2,4-Triazole, Triazole Alanine, Triazole Acetic Acid). US EPA, February 7, 2006.)

Tetraconazole Metabolites EPA "has determined that three toxicologically different groups of compounds are of concern following application of tetraconazole. The implications for risk assessment of these groups are discussed below. Free triazole metabolites (includes 1,2,4-triazole (T), triazolyl alanine (TA), triazolyl acetic acid (TAA), triazolyl hydroxypropionic acid (THP), and/or all labile conjugates of these compounds): HED has previously addressed the toxicity of T, TA and TAA in D322215 (HED Risk Assessment Document; M. Doherty et al., 7-Feb-2006). Please refer to this document for information concerning the toxicity of these free triazole metabolites. The free triazole risk assessment mentioned above pertains to exposure to T, TA, and TAA from the conazole/triazole fungicides. Tetraconazole results in the formation of these compounds as well as THP. THP is a residue of concern in rotational crops and livestock (included as a residue of concern in livestock based on the identification in rotational crops and therefore as a potential residue in feed). Based on the proposed application rates and the results of the confined rotational crop studies, HED has concluded that residues in rotational crops will be negligible; therefore, residue of THP will be negligible and the previous free-triazole risk assessment is acceptable. (Ref: Tetraconazole: Human-Health Risk Assessment for Proposed Uses on Soybean, Sugar Beet, Peanut, Pecan, and Turf. January 26, 2007 - 105 pages
Docket #: EPA-HQ-OPP-2006-0576-0010
)


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
April 11, 2007 EPA-HQ-OPP-2006-0576

Sipcam Agro USA, Inc. and Isagro S.p.A. Pesticide Tolerance. FINAL RULE.

Human Health Aggregate Risk Assessment for Triazole-derivative Fungicide Compounds (1,2,4-Triazole, Triazole Alanine, Triazole Acetic Acid). US EPA, February 7, 2006.

Hazard Characterization (Page 13)
1,2,4-triazole (free triazole) is a metabolite common to a number of triazole-derivative pesticides, and is found in both mammalian (rat) and plant metabolism studies. Although for most pesticides, mammals convert only a small proportion to free triazole (less than 25%), two compounds (tetraconazole and flusilazole) demonstrate relatively high conversion (68-77%) in rat metabolism studies. As a plant metabolite, and given the wide use of triazole-derivative pesticides (used as fungicides on many crops as well as on turf) free triazole is found in a variety of food commodities, including animal byproducts. 1,2,4-triazole appears to be relatively stable in the environment, and may be found in rotational crops as well as in water. ...

Documents in the Federal Register Docket:

Tetraconazole: Human-Health Risk Assessment for Proposed Uses on Soybean, Sugar Beet, Peanut, Pecan, and Turf. January 26, 2007 - 105 pages
Docket #: EPA-HQ-OPP-2006-0576-0010

Tetraconazole. Dietary Exposure and Risk Assessment. Application of Tetraconazole to Pecan, Sugar Beet, and Soybean. January 23, 2007 - 39 pages
Docket #: EPA-HQ-OPP-2006-0576-0011

Notice of Filing Sipcam Agro USA (PP#9F6023 and PP#6F7084) Undated - 9 pages
Docket #: EPA-HQ-OPP-2006-0576-0004

Notice of Filing Sipcam Agro USA (PP#9F5066) - Undated - 6 pages
Docket #: EPA-HQ-OPP-2006-0576-0005

Notice of Filing PP#576971 Isagro - Undated - 6 pages
Docket #: EPA-HQ-OPP-2006-0576-0007

Projected Percent Crop Treated for the Fungicide Tetraconazole - November 29, 2006 - 9 pages
Docket #: EPA-HQ-OPP-2006-0576-0009

Commodity PPM
Aspirated grain fractions 1.0
Beet sugar, dried pulp 0.15
Beet sugar, molasses 0.15
Beet sugar, root 0.05
Cattle, fat 0.02
Cattle, liver 0.20
Cattle, meat 0.01
Cattle, meat byproducts (except liver) 0.01
Eggs 0.02
Goat, fat 0.02
Goat, liver 0.20
Goat, meat 0.01
Goat, meat byproducts (except liver) 0.01
Hog, fat 0.01
Hog, liver 0.05
Hog, meat 0.01
Hog, meat byproducts (except liver) 0.01
Horse, fat. 0.02
Horse, liver 0.20
Horse, meat 0.01
Horse, meat byproducts (except liver) 0.01
Milk 0.01
Milk, fat 0.25
Peanut 0.03
Peanut, oil 0.10
Pecan 0.04
Poultry, fat 0.05
Poultry, meat 0.01
Poultry meat byproducts 0.01
Sheep, fat 0.02
Sheep, liver 0.20
Sheep, meat 0.01
Sheep, meat byproducts (except liver) 0.01
Soybean, refined oil 0.80
Soybean, seed 0.15
December 20, 2006 EPA-HQ-OPP-2006-0576

Sipcam Agro USA, Inc. Pesticide petitions.

Pesticide Petition PP 6F7084.
in or on the food commodity
-- pecan at 0.05 ppm.

Pesticide Petition PP 9F6023.
in or on the food commodity
-- peanut, nutmeat at 0.05 ppm
-- peanut, refined oil at 0.15 ppm.

Pesticide Petition PP 9F5066.
in or on the food commodities
-- sugarbeet roots at 0.05 ppm
-- sugarbeet top at 3.0
-- sugarbeet dried pulp at 0.15 ppm
-- sugarbeet molasses at 0.15 ppm
-- meat of cattle, goat, horse and sheep at 0.05 ppm
-- liver of cattle, goat, horse and sheep at 4.0 ppm
-- fat of cattle, goat, horse and sheep at 0.30 ppm
-- meat byproducts, except liver, of cattle, goat, horse and sheep at 0.10 ppm
-- milk at 0.05 ppm.

July 26, 2006 EPA-HQ-OPP-2006-0576 Isagro S.p.A. Pesticide petition: PP 5F6971.
To establish a new tolerance for residues of the fungicide tetraconazole in or on food commodities
-- soybean, aspirated grain fractions/refined oil at 0.5 parts ppm
-- soybean, seed at 0.1 ppm
-- poultry, fat at 0.05 ppm
-- poultry, egg/ liver/meat/meat byproducts at 0.01 ppm.
Dec 21, 2005 EPA-HQ-OPP-2004-0388

Pesticide Product Registrations; Conditional Approval. Notice.

This notice announces Agency approval of applications submitted by Sipcam Agro, USA Inc. to conditionally register the pesticide products, Tetraconazole Technical, EPA Registration Number 60063-11 and Eminent 125 SL Fungicide, EPA Registration Number 60063-12, containing a new active ingredient not included in any previously registered products pursuant to the provisions of section 3(c)(7)(C) of the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA), as amended.

EPA issued a notice, published in the Federal Register of October 20, 1999 which announced that Sipcam Agro, USA Inc., 70 Mansell Court, Suite 230, Roswell, GA 30076 submitted an application to register the following two pesticide products:
1. Tetraconazole Technical, (EPA File Symbol: 60063-RR). Active ingredient: Tetraconazole: at 97.0%. The application for the product Tetraconazole Technical was approved for manufacturing or formulating purposes on April 14, 2005, to use for formulation into end-use products for use on sugar beets (EPA Registration Number 60063-11).
2. Eminent 125SL Fungicide, (EPA File Symbol: 60063-RE). Active ingredient: Tetraconazole: at 11.6%. The application for the product Eminent 125SL was approved on April 14, 2005 for the control of Cercospora leaf spot and powdery mildew disease of sugar beets (EPA Registration Number 60063-12).

The Agency has considered the available data on the risks associated with the proposed use of tetraconazole, and information on social, economic, and environmental benefits to be derived from such use. Specifically, the Agency has considered the nature and its pattern of use, application methods and rates, and level and extent of potential exposure. Based on these reviews, the Agency was able to make basic health and safety determinations which show that use of tetraconazole during the period of conditional registration will not cause any unreasonable adverse effect on the environment, and that use of the pesticide is, in the public interest.

A paper copy of the fact sheet, which provides more detail on this registration, may be obtained from the National Technical Information Service (NTIS), 5285 Port Royal Rd., Springfield, VA 22161. [See EPA's April 2005 Fact Sheet - note that tetraconazole is classified as "likely to be carcinogenic to humans“ based on the occurrence of liver tumors in male and female mice.] In accordance with section 3(c)(2) of FIFRA, a copy of the approved label, the list of data references, the data and other scientific information used to support registration, except for material specifically protected by section 10 of FIFRA, are also available for public inspection. Requests for data must be made in accordance with the provisions of the Freedom of Information Act and must be addressed to the Freedom of Information Office (A-101), 1200 Pennsylvania Ave., NW., Washington, DC 20460-0001. The request should: Identify the product name and registration number and specify the data or information desired.

•• Comments submitted to US EPA on this Notice from FAN Pesticide Project.
•• FOIA Request for documents on tetraconazole.

August 31, 2005 OPP-2005-0223

Pesticide Emergency Exemptions:

• New Jersey. EPA authorized the use of tetraconazole on soybeans to control soybean rust; April 25, 2005 to November 10, 2007. Contact: (Andrew Ertman)
• Tennessee. EPA authorized the use of tetraconazole on soybeans to control soybean
rust; April 25, 2005 to November 10, 2007. Contact: (Andrew Ertman).
• Vermont. EPA authorized the use of tetraconazole on soybeans to control soybean
rust; June 23, 2005 to November 10, 2007. Contact: (Andrew Ertman)

July 13, 2005 OPP-2005-0188 Pesticide Emergency Exemptions:
Minnesota: Crisis: EPA authorized the use of tetraconazole on soybeans to control soybean rust; March 2, 2005, to March 1, 2008.
South Dakota: Quarantine: EPA authorized the use of tetraconazole on soybeans to control soybean rust; March 2, 2005, to March 1, 2008.
June 1, 2005 OPP-2005-0078 Pesticide Tolerances for Emergency Exemptions. Final Rule.
This regulation establishes time-limited tolerances for residues of tetraconazole in or on
Commodity Parts per million Expiration/ revocation date
Egg 0.03 12/31/09
Poultry, fat 0.004 12/31/09
Poultry, liver 0.03 12/31/09
Poultry, meat 0.0003 12/31/09
Poultry, meat byproduct, except liver 0.002 12/31/09
Soybean, seed 0.05 12/31/09

The States of Minnesota and South Dakota, as lead state agencies in what is essentially a ``national'' section 18 request for all soybean growing States... Soybean rust has been designated as a biosecurity threat and therefore, it is important that control measures be available for the disease.

For purposes of this section 18 petition, parent tetraconazole is being considered. The Agency does have concern about potential toxicity of 1,2,4-triazole and two conjugates, triazolylalanine and triazolyl acetic acid. These three compounds are metabolites to most of the triazole-containing fungicides. To support the extension of existing parent triazole-derivative fungicide tolerances, EPA conducted an interim human health assessment for aggregate exposure to 1,2,4-triazole. The exposure and risk estimates presented in this assessment are overestimates of actual likely exposures and therefore, should be considered to be highly conservative. Based on this assessment EPA concluded that for all exposure durations and population subgroups, aggregate exposures to 1,2,4-triazole are not expected to exceed its level of concern. This assessment should be considered interim due to the ongoing series of studies being conducted by the U.S. Triazole Task Force (USTTF). Those studies are designed to provide the Agency with more complete toxicological and residue information for free triazole and are expected to be submitted to the Agency in late 2004. Upon completion of the review of these data, EPA will prepare a more sophisticated assessment based on the revised toxicological and exposure databases.
The most recent estimated aggregate risks resulting from the use of tetraconazole, are discussed in the Federal Register of April 22, 2005 final rule (see below) establishing tolerances for residues of tetraconazole in/on sugarbeet and livestock commodities.
In that prior action, risk was estimated assuming tolerance level residues in all commodities for established and proposed tolerances, including the tolerances for soybean and animal commodities discussed in this document.

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

 
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