Hydramethylnon
CAS No. 67485-29-4
 
 

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Adverse Effects
Abstracts

ACTIVITY: Insecticide (unclassified)

CAS Name: tetrahydro-5,5-dimethyl-2(1H)-pyrimidinone [3-[4-(trifluoromethyl)phenyl]-1-[2-[4-
(trifluoromethyl)phenyl]ethenyl]-2-propenylidene]hydrazone

Structure:

Adverse Effects:

Amyloidosis - Kidney
Blood
Body Weight Decrease (including cachexia and anorexia)
Bone
Cancer: Possible Human Carcinogen - LUNG
Endocrine: Adrenal
Endocrine: Suspected Disruptor
Endocrine: Testicular
Endocrine: Thymus
Endocrine: Uterus
Kidney
Lung
Reproductive/Developmental

Environmental Effects:

Potential for accumulation in Fish

Fish: Highly to Very Highly Toxic

Regulatory Information
(only comprehensive for the US)
US EPA Registered: Yes 
US EPA PC Code: 118401  
California Chemical Code 2203 
US Tolerances: CFR 180.395 
FDA LMS Code: 754 
US EPA Permit Date
and Registrant:
1980, American Cyanamid 
European Commission: Not allowed to be used as an active ingredient after July 25, 2003. 
Registered use in
(includes only a limited list of countries)

Australia, Canada, India, Netherlands, New Zealand, Philippines, Singapore, South Africa, Tanzania, US 
US Maximum Residue Levels permitted in food commodities
Grass (pasture & rangeland)
Grass hay (pasture & rangeland)
Pineapple
Other Information
Molecular Formula: C25H24 F6 N4 
Manufacturers: BASF 
Other Names: Pyrimidinone
Amdro Fire Ant Control
Amidinohydrazone
Maxforce
Pyramdron
Siege
Wipeout
 
Of special interest:
PAN BAD ACTOR - Developmental or Reproductive Toxin 
Material Safety Data Sheets & Labels
June 2002 - Summary of Toxicology Data. California EPA.
2002 - Aventis Environmental Science has agreed to acquire the Maxforce product line from Clorox for an undisclosed sum. The Maxforce line, based on firponil or hydramethylnon, consists of a range of products to control ants and cockroaches, and is sold to the professional pest control markets in over 100 countries. Clorox will continue to sell its consumer insecticies, including the "Combat" and "Black Flag" branded products, into the consumer markets. Aventis already has the exclusive rights to market the Maxforce line in Europe, whilst also selling it in South America. Under the new agreement, Aventis will now have global rights to sell Maxforce to the professional pest control markets.
Ref: February 2002. Agrochemical Service. PhytoPhile.
December 1998 - Reregistration Eligibility Decision (RED) - US EPA (long)
December 1998 - RED Fact Sheet - US EPA (short)
TOXNET profile from Hazardous Substances Data Bank
June 30, 2004: Canada's Pest Management Regulatory Agency has determined that hydramethylnon is acceptable for continuing registration provided that some mitigation measures are implemented. Uses: as an insecticide to kill cockroaches or ants. Re-evaluation Decision Document No. RRD2004-16. Canada Pest Management Regulatory Agency.
November 26, 2002 - European Commission: Hydramethylnon is one of 320 pesticides to be withdrawn in July 2003. Some 320 substances used in plant protection products (PPPs) - including insecticides, fungicides and herbicides - are to be withdrawn from the market by 25 July 2003 as part of the European Commission's new approach to the evaluation of active substances in plant protection products. This aims to improve safeguards to ensure that all such products in use are safe for the environment and human health. Users, wholesalers and retailers of plant protection products will need to be aware of whether the products they use or sell are likely to be withdrawn, so as to prevent them being left with stocks of unusable material. Those concerned should contact their national authority to check the authorisation status for any particular product. The Regulation (ní 2076/2002 of 20 November 2002), with the list of the 320 substances, has now been published in the Offical Journal...." Ref: MIDDAY EXPRESS. News from the Press and Communication Service's midday briefing. 
Identified by the State of California as "Known to Cause Developmental Toxicity" and "Male Reproductive Toxicity" - Prop 65 
June 2002 - In Australia when Hydramethylnon is used "In bait trays for control of ants" 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  
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.  
Japan: Listed since Nov 15, 1991, as a Designated Chemical Substance. A substance which, either in itself or one of its degradation products, is not easily degradable or which may be harmful to human health when ingested continuously and which is considered to cause or expected to cause harm to human health due to significant residues of the substance in a wide range of areas. A person who manufactures or imports this substance shall for every fiscal year submit a report on manufactured or imported quantities. Division of Chem-Bio Informatics, National Institute of Health Sciences, Japan. 
October 2001 - Glossary of Pesticide Chemials. A listing of pesticides subject to analysis of residues in foods and feeds by the US Food and Drug Administration.
Abstracts 
Insecticide Products - partial list
2000 Toxic Release Inventory. Brief Summary.
Nov 14, 1996: Pyrimidinone. Case 2585. Chemical 118401. Product and Residue Chemistry Chapters for the Reregistration Eligibility Decision (RED). From K. Dockter, USEPA Chemistry Branch II to Jane Smith, USEPA Risk Characterization & Analysis Branch. August 1, 2007, Docket EPA-HQ-OPP-2004-0154-0013.
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: Hydramethylnon 

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

In a 90-day dog feeding study, testicular atrophy was observed at 6 mg/ kg/day (LOEL). The NOEL was 3 mg/kg/day. In a 90-day rat study, dietary administration of 5 mg/kg/day (LOEL) produced testicular atrophy. The NOEL was 2.5 mg/kg/day. Dietary administration of 6.5 mg/kg/day for 18 months produced testicular lesions in mice. The NOEL was 2.75 mg/kg/ day. In a 2-year rat study, dietary administration of 5 mg/kg/day produced decreased testicular weight and testicular atrophy. The NOEL was 2.5 mg/kg/day. In a 3-generation rat reproduction study, oral administration of 5 mg/kg/day produced male infertility. The NOEL was 2.5 mg/kg/day.

Decreased fetal weight was observed in the offspring of rats administered 30 mg/kg/day (LOEL). The NOEL was 10 mg/kg/day. Increased post implantation loss and decreased fetal viability were observed in the offspring of rabbits administered 15 mg/kg/day (LOEL). The NOEL was 5 mg/kg/day. Vertebral anomalies were seen in the offspring of rabbits administered 10 mg/kg/day (LOEL). The NOEL was 5 mg/kg/day.

Dietary administration of 1 mg/kg/day (LOEL) for 6 months to dogs produced increased absolute and relative liver weights. The NOEL was 0.33 mg/kg/day. Based on the NOEL of the study, an oral RfD of 0.0003 mg/kg/day was derived.

EPA believes that there is sufficient evidence for listing hydramethylnon on EPCRA section 313 pursuant to EPCRA section 313(d)(2)(B) based on the available reproductive, developmental, and hepatic toxicity data for this chemical.

The 96-hour LC 50 in the Chanel Catfish was 90 ppb. Bioaccumulation factors in bluegill sunfish are 1300 for the whole fish, 780 for the fillet, and 1900 for viscera. EPA believes that there is sufficient evidence for listing hydramethylon on EPCRA section 313 pursuant to EPCRA section 313(d)(2)(C) based on the available environmental toxicity data and the potential for bioaccumulation.

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.



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
Fluorinated pesticides cited:
Active Ingredient Product Name   Active Ingredient Product Name
Benefin
(also known as
Benfluralin)
Team,
XL 2G
  Hydramethylnon MaxForce Ant Killer Granular Bait,
MaxForce Roach Gel,
Siege
Bifenthrin Talstar Lawn & Tree   Lambda-cyhalothrin Demand CS
Bromethalin Vengence   Sulfuryl fluoride Vikane
Cyfluthrin Intruder HPX,
Tempo 20 WP
  Trifluralin Team,
Turflan
Fipronil MaxForce Ant Station,
MaxForce Roach Station,
MaxForce FC
  Unknown Fluorgard
Fluazifop-butyl Fusilade,
Fusilade II,
Ornamec
  -

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
August 1, 2007 EPA-HQ-OPP-2004-0154

Proposal to Increase tolerances. Hydramethylnon (Pyrimidinone). EPA is increasing the following commodity tolerances in 40 CFR 180.395(a):

``grass (pasture and rangeland)'' from 0.05 ppm to 2.0 ppm

and revising the terminology to ``grass, forage'' and ``grass, hay;'' based on available field trial data which show residues of hydramethylnon above the current tolerance level and label amendments which reflect parameters of use patterns for which field trials are available; (i.e., reflect a 0 day post harvest interval) since the Agency no longer allows a PHI (post harvest interval) restriction on grass. The tolerance for ``grass hay (pasture and rangeland)'' was recommended to be increased from 0.05 ppm to 0.1 ppm, based on available field trial data previously discussed and label amendments which reflect a 0 day post harvest interval. However, because the terminology should be revised to ``grass, hay,'' that tolerance at 0.1 ppm is no longer needed since it would be a duplicate covered by the proposed tolerance at 2.0 ppm. Therefore, EPA is removing the tolerance in 40 CFR 180.395(a) for grass hay (pasture and rangeland).
After the hydramethylnon RED was completed in 1998, a permanent tolerance was established in 40 CFR 180.395(a) on pineapple (68 FR 48302, August 13, 2003)(FRL-7319-5). Since the proposal of August 4, 2004 (69 FR 47051), the time-limited tolerance for hydramethylnon residues on pineapple in 40 CFR 180.395(b), for section 18 emergency exemptions, expired on June 30, 2005. The Agency did not propose in a notice for comment to remove the text and table with the expired tolerance and reserve 40 CFR 180.395(b). However, section 553(b)(3)(B) of the Administrative Procedure Act provides that notice and comment is not necessary ``when the agency for good cause finds (and incorporates the finding and a brief statement of reasons therefore in the rules issued) that notice and public procedure thereon are impracticable, unnecessary, or contrary to the public interest.'' Consequently, for good cause, EPA is removing the text and table from 40 CFR 180.395(b) and reserving that section for emergency exemptions in this document. The reason for taking this action is because such action has no practical impact on the use of or exposure to the pesticide active ingredient, hydramethylnon, since the sole time-limited tolerance in 40 CFR 180.395(b) had expired and, as it no longer needs to be codified in that section, should be removed for the sake of clarity.
•• Document made available with this notice:

Nov 14, 1996: Pyrimidinone. Case 2585. Chemical 118401. Product and Residue Chemistry Chapters for the Reregistration Eligibility Decision (RED). From K. Dockter, USEPA Chemistry Branch II to Jane Smith, USEPA Risk Characterization & Analysis Branch. August 1, 2007, Docket EPA-HQ-OPP-2004-0154-0013.

August 3, 2005 OPP-2005-0201

Cancellation of Pesticides for Non-payment of Year 2005 Registration Maintenance Fees.

Section 24(c) Registrations canceled for non-payment of the 2005
maintenance fee are shown in the following Table 1:

Table 1.--Section 24(c) Registrations Canceled for Non-Payment of Maintenance Fee

SLN no. Product Name
000241 TX-01-0016 Amdro Fire Ant Insecticide
Oct 27, 2004 OPP-2004-0338 Cancellation of Pesticides for Non-payment of Year 2004 Registration Maintenance Fees.
Table 1.--Section 24(c) Registrations Canceled for Non-Payment of
Maintenance Fee
Name of Pesticide Product Name Registrant SLN No.
Hydramethylnon

Amdro Fire Ant Insecticide

BASF Corporation 000241 HI-02-0003
Hydramethylnon Amdro Fire Ant Insecticide BASF Corporation 000241 HI-02-0009.
August 4, 2004 OPP-
2004-0154

Tolerances increased and terminology revision. EPA is proposing to increase the tolerance in 40 CFR 180.395(a) on ``grass (pasture and rangeland)'' from 0.05 to 2.0 ppm and revise the terminology to ``grass, forage'' and ``grass, hay;'' based on available field trial data which show residues of hydramethylnon above the current tolerance level and label amendments which reflect parameters of use patterns for which field trials are available; i.e., reflect a zero day post harvest interval since that the Agency no longer allows a PHI restriction on grass.

Section 180.395 is amended by revising the table in paragraph (a) to read as follows:
Commodity
Parts per million
Grass, forage
2.0
Grass, hay
2.0
Pineapple
0.05
Nov 26, 2003 OPP-2003-0358 Pesticide Emergency Exemption. A ``specific exemption'' authorizes use of a pesticide against specific pests on a limited acreage in a particular State.
-- Hawaii Department of Agriculture. Specific. EPA authorized the use of hydramethylnon on pineapple to control big-headed and Argentine ants; June 6, 2003 to June 24, 2004.
Aug 13, 2003 OPP-2003-0251 BASF. Pesticide Tolerance for Pineapple at 0.05 ppm. FINAL RULE.
The US EPA Cancer Peer Review Committee classified hydramethylnon as a Group C-possible human carcinogen, and recommended that, for the purpose of risk characterization, the Reference Dose approach should be used for quantification of human risk. This classification was based upon statistically significant increases in lung adenomas and combined lung adenomas/carcinomas in female mice.
Subchronic, Chronic, and Other Toxicity (from Table 1.)
Study Type Results
Rat -
Subchronic Feeding
NOAEL = 2.5 mg/kg/ - Rat day LOAEL = 5.0 mg/kg/ day - decreased testicular weights (34%), and testicular atrophy.
Dog - Subchronic Gavage NOAEL = 3 mg/kg/ day - LDT; decreased food consumption (11%/ 20%, males/ females) and body weight gain (11%/ 9%, males/ females). LOAEL = not defined Lethal Dose = 6 mg/kg/day - decreased food consumption and body weight gain, SGPT, cachexia, wasting of muscle and subcutaneous fat, testicular atrophy, and death.
Rabbit -
21-Day Dermal
NOAEL = 250 mg/kg/day (HDT) Food consumption was depressed as much as 38% and 45% in the high- dose males and females, compared to controls. The high-dose males and females weighed as much as 8% and 9% less than the controls. The platelet count in the high-dose females at termination was 54% less than controls, but was not considered adverse because it is a common finding following skin abrasion.
Rat - Developmental Toxicity Maternal NOEL = 3 mg/kg/day Maternal NOAEL = 10 mg/kg/day - 8% decrease in body weight and yellowish discoloration of the fat. Maternal LOAEL = 30 mg/kg/day - 16% decrease in body weight; increased incidence of nasal mucus, alopecia, soft stools, staining of the anogenital fur, yellowish discoloration of the fat, and small thymus. Developmental NOEL = 10 mg/kg/ day Developmental LOAEL = 30 mg/kg/ day - decreased mean fetal weights and increased incidence of rudimentary structures and incompletely ossified supraoccipitals. At 30 mg/kg/day, a 16% decrease in maternal body weight, increased incidence of clinical signs (nasal mucus, alopecia, soft stool, staining of anogenital fur), yellowish discoloration of the fat, and small thymus were observed.
Rabbit - Developmental Toxicity ... Developmental NOAEL = 5 mg/kg/ day - decreased fetal weight (8%). Developmental LOAEL = 10 mg/kg/ day - abortions, decreased fetal weight (16%).
Rat -
2-Generation Reproductive Toxicity
Reproductive/ Systemic NOAEL = 25 ppm (1.66/2.01 mg/kg/day, male/ female) Reproductive/ Systemic LOAEL = 50 ppm (3.32 / 4.13 mg/kg/day, male/female) (degeneration of the germinal epithelium (1/29) and aspermia (1/ 29)
Mouse -
Carcinogenicity Feeding (18 months)
NOAEL = 25 ppm (3.57 mg/kg/day) in males NOAEL = not defined in females. LOAEL = 50 ppm (6.93 mg/kg/day) in males (testicular lesions) LOAEL = 25 ppm (4.45 mg/kg/day) in females (LDT; combined lung adenomas and carcinomas) The high-dose females were sacrificed after 5 weeks due to high mortality.
Rat -
Chronic Feeding Toxicity/ Carcinogenicity
NOAEL = 50 ppm (2.4 mg/kg/day in males, 3.0 mg/kg/ day in females) LOAEL = 100 ppm (4.9 mg/kg/day in males, 6.2 mg/kg/ day in females) (small, soft testes, decreased testicular weights, and testicular atrophy in males; decreased body weight gain in females)

Conditions The following studies are required to further characterize the environmental effects of hydramethylnon:
-- Estuarine/marine fish LC
50 (72-1),
-- Estuarine/marine invertebrate EC50 (72-2), and
-- Sediment Toxicity Testing (Harmonized guidelines 850.1735 and 850.1740).

In addition, the following studies are required for any future expansion of hydramethylnon uses:
-- Aquatic Photodegradation (161- 2),
-- Aerobic Aquatic Metabolism (162-4), and
-- Terrestrial Field Dissipation (164-1).

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

 
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