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Hydramethylnon

HCID 49901
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
67485-29-4
Standard SMILES
CC1(C)CN=C(NN=C(C=Cc2ccc(C(F)(F)F)cc2)C=Cc2ccc(C(F)(F)F)cc2)NC1
InChIKey
IQVNEKKDSLOHHK-UHFFFAOYSA-N
Molecular formula
C25H24F6N4
Average molar mass
494.5 g/mol
Monoisotopic mass
494.19051575

Overview

Hydramethylnon appears as odorless yellow crystals. Insoluble in water. Used as an insecticide.

Names & identifiers

Preferred name
Hydramethylnon
IUPAC
N-[1,5-bis[4-(trifluoromethyl)phenyl]penta-1,4-dien-3-ylideneamino]-5,5-dimethyl-4,6-dihydro-1H-pyrimidin-2-amine
English name
Hydramethylnon
Molecular formula
C25H24F6N4
Molecular weight
494.48

Names & synonyms

hydromethylnonDTXSID6023868CHEBI:2630NSC-379665AC-217300RefChem:788601DTXCID608102635,5-Dimethyl-perhydro-pyrimidin-2-one alpha-(4-trifluoromethylstyryl)-alpha-(4-trifluoromethyl)cinnamylidenehydrazone405-090-9614-073-7TETRAHYDRO-5,5-DIMETHYL-2(1H)-PYRIMIDINONE(3-(4-(TRIFLUOROMETHYL)PHENYL)-1-(2-(4-(TRIFLUOROMETHYL)PHENYL)ETHENYL)-2-PROPENYLIDENE)HYDRAZONE2(1H)-Pyrimidinone, tetrahydro-5,5-dimethyl-, (3-(4-(trifluoromethyl)phenyl)-1-(2-(4-(trifluoromethyl)phenyl)ethenyl)-2-propenylidene)hydrazone
Show more names
HydramethylonMatoxWipeoutMAXFORCEac217300cl217300
5,5-dimethyltetrahydropyrimidin-2(1H)-one (3-(4-(trifluoromethyl)phenyl)-1-(2-(4-(trifluoromethyl)phenyl)ethenyl)prop-2-en-1-ylidene)hydrazone67485-29-4AC 217300AmdroCL 217300CombatHydramethylnonJ265GZ7MFJ

Properties

Computed structural properties

XLogP
6.4
Topological polar surface area
48.8 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
8
Rotatable bonds
6
Heavy atoms
35
Formal charge
0
Complexity
763

Experimental & physicochemical properties

Chemical ClassesTeratogens
PFASPFAS -> PFAS identified in REACH Regulation EC No. 1272/2008
Pesticides · 4 items

Pesticide -> EPA IRIS

Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Other Insecticides

LogP · 2 items

log Kow = 2.31

2.31

OdorCharacteristic of vegetable oil
Color/Form · 3 items

Yellow to tan crystals

Yellow-tan, free-flowing granules

Crystals from isopropanol

Solubility · 2 items

In acetone 360, ethanol 72, 1,2-dichloroethane 170, methanol 230, isopropanol 12, xylene 94, chlorobenzene 390 (all in g/L at 20 °C)

In water, 0.006 mg/L at 25 °C

Flash Point>220 °F (SFCC)
Endocrine Disruptors

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P260, P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P319, P330, P337+P317, P391, and P501 (click each P-code to see the statement)

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P304+P340, P305+P351+P338, P317, P318, P319, P330, P337+P317, P391, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 6 items

Hazard Traits - Developmental Toxicity; Reproductive Toxicity

2(1H)-Pyrimidinone, tetrahydro-5,5-dimethyl-, [3-[4-(trifluoromethyl)phenyl]-1-[2-[4-(trifluoromethyl)phenyl]ethenyl]-2-propenylidene]hydrazone is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2(1H)-Pyrimidinone, tetrahydro-5,5-dimethyl-, [3-[4-(trifluoromethyl)phenyl]-1-[2-[4-(trifluoromethyl)phenyl]ethenyl]-2-propenylidene]hydrazone are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Hydramethylnon is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2002/2076

REACH registered substance: 5,5-dimethyl-perhydro-pyrimidin-2-one α-(4-trifluoromethylstyryl)-α-(4-trifluoromethyl)cinnamylidenehydrazone (EC: 405-090-9)

Hydramethylnon: HSNO Approval: HSR003435 Approved with controls

DOT LabelClass 9
Fire HazardsExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Health HazardsExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

... The most abundant metabolite /in rats/ was CL 98,724: 1,5- bis(alpha,alpha,alpha-trifluoro-p-tolyl)-1,4-pentadien-3-one. ...

Sprague-Dawley rats were dosed with hydramethylnon ( ... CL 217,300) by gavage in corn oil at low (3 mg/kg) or high (100 mg/kg) single doses. Also, multiple-dosing was done with 14 consecutive daily treatments of 3 mg/kg, followed by 3 mg/kg of labeled hydramethylnon. In all cases, both phenyl and pyrimidinyl ring-labeled treatments were evaluated. There were no substantial differences associated with sex, dose level, or duration of treatment. ... The two main identified urinary metabolites were a substituted cinnamic acid and a substituted p-toluic acid. ... The major labeled component of tissues was parent compound, with appreciable amounts of moderately polar material as the second-most abundant fraction. ...

MeSH Pharmacological ClassificationPesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.
Absorption, Distribution and Excretion · 5 items

In rats, following oral admin, rapidly eliminated in the feces and urine.

No residues were detectable in the milk or tissues of goats (0.2 mg/kg in the daily diet for 8 days). No residues were found in the milk or tissues of cows (0.05 mg/kg for 21 consecutive days).

Sprague-Dawley rats were dosed with hydramethylnon ( ... CL 217,300) by gavage in corn oil at low (3 mg/kg) or high (100 mg/kg) single doses. Also, multiple-dosing was done with 14 consecutive daily treatments of 3 mg/kg, followed by 3 mg/kg of labeled hydramethylnon. In all cases, both phenyl and pyrimidinyl ring-labeled treatments were evaluated. There were no substantial differences associated with sex, dose level, or duration of treatment. Elimination was relatively rapid. Most of the label was excreted within 36 hr. Label was excreted principally in feces (about 90%). Parent compound was the major labeled fecal component (70-85% of administered doses ... ). Urinary elimination was about 1-4% of total administered compound ... . The two main identified urinary metabolites were a substituted cinnamic acid and a substituted p-toluic acid. Residues remaining in tissues after 7 days ranged from 3 to 10% of administered dose. The major labeled component of tissues was parent compound, with appreciable amounts of moderately polar material as the second-most abundant fraction. Data suggest inefficient absorption and a modest rate of metabolism of absorbed hydramethylnon. ...

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
67485-29-4
PubChem CID
49901
DTXSID
DTXSID6023868
ChEMBL
CHEMBL464812
EC Number
405-090-9、614-073-7
Potential endocrine disrupting compound
DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxide and hydrogen fluoride/
Melting Point190 °C
Vapor Pressure · 3 items

0.00000002 [mmHg]

Yellow to tan crystalline solid with characteristic vegetable odor. MP 189-191 °C. Insoluble in water, slightly soluble in alcohols, and soluble in acetone, chorobenzene, and 1,2-dichloroethane. VP: 2X10-8 mm Hg at 25 °C. /Technical/

2.03X10-8 mm Hg at 25 °C

Physicochemical properties

Melting point
185 · 185-190°C
Boiling point
510.5 · 510.5±60.0 °C(Predicted)
Density
1.2816 · 1.2816 (estimate)
vapor pressure
2.7 x · 2.7 x l0-6 Pa (25 °C)
storage temp.
0 · 0-6°C
solubility
Chloroform (Slightly), DMSO (Sparingly), Methanol (Slightly)
Water Solubility
0.005 · 0.005-0.007 mg l-1(25 °C)
pka
14.38 · 14.38±0.40(Predicted)
BRN
6015162 · 6015162
Henry's Law Constant
4.5 · 4.5×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Stability
Light Sensitive
Major Application
agricultureenvironmental
InChIKey
IQVNEKKDSLOHHK-FNCQTZNRSA-N
SMILES
CC1(C)CN\C(NC1)=N\N=C(\C=C\c2ccc(cc2)C(F)(F)F)/C=C/c3ccc(cc3)C(F)(F)F
CAS DataBase Reference
67485 · 67485-29-4(CAS DataBase Reference)
FDA UNII
265 GZ7MFJ · J265GZ7MFJ
Proposition 65 List
Hydramethylnon
NIST Chemistry Reference
2 · 2(1H)-pyrimidinone, tetrahydro-5,5-dimethyl-, (3-(4-(trifluoromethyl)phenyl)-1-(2-(4-(trifluoromethyl)phenyl)ethenyl)-2-propenylidene)hydrazone(67485-29-4)
EPA Substance Registry System
Hydramethylnon (67485-29-4)
Pesticides Freedom of Information Act (FOIA)
Amdro
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07,GHS08,GHS09
Signal word
Danger
Hazard statements
302 · H302-H319-H372-H410
Precautionary statements
273 · P273-P301+P312+P330-P305+P351+P338-P314
Hazard Codes
T;N,N,T
Risk Statements
22 · 22-36-48/25-50/53
Safety Statements
1 · 1/2-22-26-36/37-45-60-61
RIDADR
3077 · UN3077 9/PG 3
WGK Germany
3 · 3
RTECS
7583000 · UW7583000
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
4 OralAquatic · Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2STOT RE 1 Oral
Hazardous Substances Data
67485 · 67485-29-4(Hazardous Substances Data)
REACH Registrations
Inactive
Hazards SummaryAn eye irritant; [eChemPortal: ERMA; ESIS]
Reactive GroupAmines, Phosphines, and Pyridines
Special Reports · 1 item

USEPA/OPPTS; Reregistration Eligibility Decisions (REDs) Database on Hydramethylnon (67485-29-4). 155 pp. USEPA 738-R-98-023. Dec 1998. This document provides a thorough review of the scientific data underlying hydramethylnon's registration and fulfills the EPA's requirement to determine whether pesticides containing the active ingredient hydramethylnon are eligible for reregistration before calling in data on products.

FIFRA Requirements · 3 items

Tolerances are established for residues of the insecticide tetrahydro-5,5-dimethyl-2(1H)-pyrimidinone(3-(4-(trifluoromethyl)phenyl)-1-(2-(4-(trifluoromethyl)phenyl)ethenyl)-2-propenylidene)hydrazone in or on the following raw agricultural commodities: [Table#6165]

Section 4(g)(2)(A) of FIFRA calls for the Agency to determine, after submission of relevant data concerning an active ingredient, whether products containing the active ingredient are eligible for reregistration. The Agency has previously identified and required the submission of the generic (i.e. active ingredient specific) data required to support reregistration of products containing hydramethylnon. The Agency has completed its review of these generic data and has determined that the data are sufficient to support reregistration of all products containing hydramethylnon. Appendix B identifies the generic data requirements that the Agency reviewed as part of its determination of reregistration eligibility of hydramethylnon and lists the submitted studies that the Agency found acceptable. The data identified in Appendix B were sufficient to allow the Agency to assess the registered uses of hydramethylnon, and to determine that hydramethylnon can be used without resulting in unreasonable adverse effects to humans and the environment. The Agency therefore finds that all products containing hydramethylnon as the active ingredient are eligible for reregistration.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Tetrahydro-5,5-dimethyl-2(1H)-pyrimidinone is found on List B. Case No: 2585; Pesticide type: insecticide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.; Active ingredient (AI): tetrahydro-5,5-dimethyl-2(1H)-pyrimidinone; Data Call-in (DCI) Date(s): 4/12/91, 7/12/91, 3/3/95, 10/13/95; AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

Reactivity ProfileHYDRAMETHYLNON is a trifluoromethyl amidinohydrazone.
Air and Water ReactionsInsoluble in water. Hydrolysis occurs rapidly at low and high pHs.
Hazard Classes and Categories · 6 items

Acute Tox. 4 (100%)

Acute Tox. 4 (100%)

Specific target organ toxicity (repeated exposure) - category 1

Acute toxicity (Oral) - Category 4

Teratogens

Acute Tox. 4 *

Safety & protection

Fire FightingExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
First AidExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Fire Fighting ProceduresWater, foam, carbon dioxide, or dry chemical.
Storage Conditions · 2 items

Store in a cool, dry, secure place and keep container tightly closed. Use product within 3 months after opening for best results.

Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water. /Residential uses/

Cleanup Methods · 3 items

Sweep up any spill and place in a closed container for disposal.

If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label./Residential uses/

After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash. /Residential uses/

Nonfire Spill ResponseExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Disposal Methods · 3 items

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal. /Residential uses/

Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it. /Residential uses/

Preventive Measures · 5 items

Users must follow manufacturer's instructions for cleaning/maintaining PPE. If no such instructions for washables exist, use detergent and hot water. Keep and wash PPE separately from other laundry.

User Safety Recommendations: Wash hands before eating, drinking, chewing gum, using tobacco, or using the toilet. Remove clothing/PPE immediately if pesticide gets inside and then wash thoroughly and put on clean clothing. Remove PPE immediately after handling hydramethylnon, wash the outside of gloves before removing, and as soon as possible, wash thoroughly and change into clean clothing.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Do not apply this product in a way that will contact workers or other persons, either directly or through drift. Only protected handlers may be in the area during application.

For more Preventive Measures (Complete) data for HYDRAMETHYLNON (11 total), please visit the HSDB record page.

Isolation and EvacuationExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Allowable Tolerances · 1 item

Tolerances are established for residues of the insecticide tetrahydro-5,5-dimethyl-2(1H)-pyrimidinone(3-(4-(trifluoromethyl)phenyl)-1-(2-(4-(trifluoromethyl)phenyl)ethenyl)-2-propenylidene)hydrazone in or on the following raw agricultural commodities: [Table#6164]

Personal Protective Equipment (PPE) · 3 items

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

End Use Products Intended for Occupational Use (WPS and Non-WPS)): Applicators and other handlers must wear: long-sleeve shirt and long pants, water-resistant gloves, and shoes plus socks.

A 12-hour restricted entry interval (REI) is required. The PPE required for early entry is: coveralls, water resistant gloves, and shoes plus socks.

Toxicology

Target OrgansHepatic
Ecotoxicity Values · 5 items

LD50 /Anas platyrhynchos/ (Mallard duck) oral >2,510 mg/kg

LD50 /Colinus virginianus/ (Bobwhite quail) oral 1,828 mg/kg

LC50 Anas platyrhynchos (Mallard duck, age 14 days) diet 4355 ppm for 8 days (95% confidence interval: 2877-6592 ppm)[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on Tetrahydro-5,5-dimethyl-2(1H)-pyrimidio[3-[4-Trifluoromethyl)phenyl]-1-[2-

LC50 Colinus virginianus (Northern bobwhite, age 14 days) diet 1136 ppm for 8 days (95% confidence interval: 908-1420 ppm)[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on Tetrahydro-5,5-dimethyl-2(1H)-pyrimidio[3-[4-Trifluoromethyl)phenyl]-1-[2-

For more Ecotoxicity Values (Complete) data for HYDRAMETHYLNON (32 total), please visit the HSDB record page.

Environmental Fate · 4 items

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 3,300 and 8,677(2) indicate that hydramethylnon is expected to have very slight to no mobility in soil(SRC). Volatilization of hydramethylnon from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.20X10-6 atm-cu m/mole(SRC), based upon its vapor pressure, 2.03X10-8 mm Hg(3), and water solubility, 6.0X10-3 mg/L(3). Hydramethylnon is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Photolysis on soil is diphasic with a half-life of 4 days for the first phase and about 30 days for the second phase(2). A biodegradation half-life for aerobic soil metabolism of 385 days(2) suggests that biodegradation is not an important environmental fate process in soil(SRC).

TERRESTRIAL FATE: The half-life of hydramethylnon in sandy loam was approximately 7 days, 28 days when incorporated into the soil(1). Using test field plots in Florida and Texas, half-lives of 3 days and 55, respectively, were observed with no detections below the 0-6 inch soil depth. Hydramethylnon is reported as persistent and immobile below soil surfaces(2).

AQUATIC FATE: Based on a classification scheme(1), Koc values of 3,300 and 8,677(2) indicate that hydramethylnon is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.2X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 2.03X10-8 mm Hg(4), and water solubility, 6.0X10-3 mg/L(4). The photolysis half-lives in aqueous suspension at 25 °C have been reported as 24-33 days (pH 9), 10-11 days (pH 7.02), and 11-12 days (pH 8.87)(4). According to a classification scheme(5), a BCF of 1,300(2), suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC). The half-life for anaerobic aquatic metabolism ranges from 445 to 552 days(2) which suggests that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hydramethylnon, which has a vapor pressure of 2.03X10-8 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase hydramethylnon is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 3 hrs(SRC), calculated from its rate constant of 1.35X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase hydramethylnon may be removed from the air by wet or dry deposition(SRC). Hydramethylnon is rapidly degraded in sunlight by photolysis, with a half-life of approximately 1 hour(2).

Food Survey ValuesNegligible residues of hydramethylnon were found in radishes, barley, and french beans planted three months after treatment of the soil(1).
Milk Concentrations · 1 item

EXPERIMENTAL: No residues of hydramethylnon were detectable in the milk of goats after being exposed to 0.2 mg/kg hydramethylnon in the daily diet for 8 days(1). No residues were found in the milk of cows after being exposed to 0.05 mg/kg hydramethylnon for 21 consecutive days(1).

Ecotoxicity Excerpts · 4 items

/BIRDS and MAMMALS/ An acute oral toxicity study using the technical grade of the active ingredient (TGAI) was conducted to establish the toxicity of hydramethylnon to birds. In Northern bobwhite quail (Colinus virginianus) administered 92% a.i. the LD50 was 1828 mg/kg, leading EPA to conclude that the substance was slightly toxic to bobwhite quail. In Mallard duck (Anas platyrhynchos) administered 92% a.i. the LD50 was 2510 mg/kg, leading EPA to conclude that the substance was practically nontoxic to Mallard ducks. Two avian subacute toxicity tests were also available. In Northern bobwhite quail (Colinus virginianus) 92% a.i. had an 5-day LC50 of 1136 ppm and in Mallard duck (Anas platyrhynchos) 92% a.i. had a 5-day LC50 of 4355 ppm. EPA judged both studies as showing hydramethylnon to be slightly toxic.

/BIRDS and MAMMALS/ Wild mammal testing is required /by EPA for pesticides/ on a case-by-case basis, depending on the results of lower tier laboratory mammalian studies, intended use pattern and pertinent environmental fate characteristics. In most cases, rat or mouse toxicity values obtained from the Agency's files substitute for wild mammal testing. ... In the Norway Rat (Rattus norvegicus), 95% a.i. administered orally produced an LD50 of 817 mg/kg (m) and 1502 mg/kg (f); combined: 1146 mg/kg; EPA considered this information that hydramethylnon is slightly toxic in an acute oral test. In a 3-generation reproductive study in Norway Rat (Rattus norvegicus), administration of 92% a.i. resulted in male infertility at 100 ppm.

/AQUATIC SPECIES/ Two freshwater fish toxicity studies using the technical grade active ingredient were required by EPA to establish the toxicity of hydramethylnon to fish. Three acute studies of 92% a.i. were available. The 96 hr LC50s indicated that hydramethylnon is highly toxic to Rainbow trout (Oncorhynchus mykiss), moderately toxic to Bluegill sunfish (Lepomis macrochirus), and very highly toxic to Channel catfish (Ictalurus punctatus). In a freshwater aquatic invertebrate toxicity test, a 48-hour LC50/ EC50 of 1.14 ppm indicated that the 92% a.i. was moderately toxic to the waterflea (Daphnia magna).

/OTHER TERRESTRIAL SPECIES/ A honey bee acute contact study using the technical grade active ingredient was required for hydramethylnon because its outdoor use may result in honey bee exposure. The LD50 of 68.0 g/bee using 96.8% a.i. demonstrated that hydramethylnon is practically non-toxic to bees on an acute contact basis.

Plant ConcentrationsResidues of hydramethylnon in grass four months after treatment were <0.01 ppm(1).
Animal Concentrations · 1 item

No residues of hydramethylnon were detectable in tissues of goats after being exposed to 0.2 mg/kg hydramethylnon in the daily diet for 8 days(1). No residues were found in tissues of cows after being exposed to 0.05 mg/kg hydramethylnon for 21 consecutive days(1).

Acute Toxicity LinkChemical: AMDRO
EPA IRIS Information · 3 items

Amdro

Hepatic

3 x 10 ^-4 mg/kg-day

Soil Adsorption/Mobility · 1 item

Koc values of hydramethylnon have been reported as ranging from 3,300 to 8,677 using loamy sand, sandy loam, loam and silt loam soils, with reported Kds of 1,039-1,782 mL/g(1). According to a classification scheme(2), these Koc values suggest that hydramethylnon is expected to be slightly mobile to immobile in soil.

Artificial Pollution SourcesHydramethylnon's production may result in its release to the environment through various waste streams; its use as an insecticide(1) will result in its direct release to the environment(SRC).

Regulatory information

FIFRA Requirements · 3 items

Tolerances are established for residues of the insecticide tetrahydro-5,5-dimethyl-2(1H)-pyrimidinone(3-(4-(trifluoromethyl)phenyl)-1-(2-(4-(trifluoromethyl)phenyl)ethenyl)-2-propenylidene)hydrazone in or on the following raw agricultural commodities: [Table#6165]

Section 4(g)(2)(A) of FIFRA calls for the Agency to determine, after submission of relevant data concerning an active ingredient, whether products containing the active ingredient are eligible for reregistration. The Agency has previously identified and required the submission of the generic (i.e. active ingredient specific) data required to support reregistration of products containing hydramethylnon. The Agency has completed its review of these generic data and has determined that the data are sufficient to support reregistration of all products containing hydramethylnon. Appendix B identifies the generic data requirements that the Agency reviewed as part of its determination of reregistration eligibility of hydramethylnon and lists the submitted studies that the Agency found acceptable. The data identified in Appendix B were sufficient to allow the Agency to assess the registered uses of hydramethylnon, and to determine that hydramethylnon can be used without resulting in unreasonable adverse effects to humans and the environment. The Agency therefore finds that all products containing hydramethylnon as the active ingredient are eligible for reregistration.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Tetrahydro-5,5-dimethyl-2(1H)-pyrimidinone is found on List B. Case No: 2585; Pesticide type: insecticide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.; Active ingredient (AI): tetrahydro-5,5-dimethyl-2(1H)-pyrimidinone; Data Call-in (DCI) Date(s): 4/12/91, 7/12/91, 3/3/95, 10/13/95; AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

Safety data

wgk
3
rtecs
UW7583000
ridadr
UN3077 9/PG 3
risk_code
22-36-48/25-50/53
Signal word
Danger
Symbol(GHS)
GHS07,GHS08,GHS09
hazard_code
T;N,N,T
safety_code
1/2-22-26-36/37-45-60-61
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard statements
H302-H319-H372-H410
REACH Registrations
Inactive
Hazard Classifications
Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2STOT RE 1 Oral
Precautionary statements
P273-P301+P312+P330-P305+P351+P338-P314
Hazardous Substances Data
67485-29-4(Hazardous Substances Data)

... This rat study found that 71.5% of oral dose was eliminated in feces unchanged. The lesser amounts of label found in urine yielded no parent compound, but rather a number of polar metabolites. In tissues sampled (including liver), parent compound was generally the most abundant labeled moiety. The most abundant metabolite was CL 98,724: 1,5- bis(alpha,alpha,alpha-trifluoro-p-tolyl)-1,4-pentadien-3-one. ...

For more Absorption, Distribution and Excretion (Complete) data for HYDRAMETHYLNON (6 total), please visit the HSDB record page.

Uses & manufacturing

Uses · 6 items

Used as slow-acting stomach poison insecticide for control of ants and cockroaches; [HSDB]

Farming (Pesticides) [Category: Industry]

For hydramethylnon (USEPA/OPP Pesticide Code: 118401) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Insecticide for ants (big headed, fire, harvester)

Slow activating stomach poison insecticide

A slow-acting toxicant used successfully in bait for the fire ant, other ants, and cockroaches

U.S. Production2023: <50,000 lb
Industry UsesIntermediate
Methods of Manufacturing4-(Trifluormethylbenzaldehyde) + acetone + hydrazine + neopentyl glycol + urea (carbonyl condensation/ imine formation/ condensation/ imine formation)
Formulations/Preparations · 5 items

Formulations: Oil bait

AMDRO GRANULAR INSECTICIDE: Active Ingredient 0.88% Hydramethylnon

AMDRO 20 FIREANT INSECTICIDE: Active Ingredient 0.88% Hydramethylnon.

HYDRAMETHYLNON TECHNICAL INSECTICIDE: Active Ingredient 98% Hydramethylnon.

For more Formulations/Preparations (Complete) data for HYDRAMETHYLNON (38 total), please visit the HSDB record page.

Household ProductsInformation on 15 consumer products that contain Hydramethylnon in the following categories is provided:
Use ClassificationINSECTICIDES
General Manufacturing Information · 2 items

All Other Basic Organic Chemical Manufacturing

Registered for the control of ants in grasses and non-crop lands such as lawns, turfs, and non-bearing nursery stocks. Also registered for the control of ants and cockroaches in non-food use areas in domestic dwellings and commercial establishments.

Applications · 4 items

DescriptionHydramethylnon is an organic pesticide active ingredient from the trifluoromethyl aminohydrazone chemical class. It is a registered chemical alternative for chlorpyrifos for use as a termiticide and against ants, crickets, and cockroaches around the home and lawn. Hydramethylnon is also used in a wide variety of professional pesticide products and in various formulations, These include foaming products, granular products, gel baits, liquid concentrates.

HistoryHydramethylnon was developed by DuPont in 1975 and introduced to ornamentals industry in the 1990s. Acequinocyl was also discovered by DuPont in the 1970s and further developed by AgroKanesbo Co. Ltd. and Tomen Agro in Japan. Arysta LifeScience first introduced acequinocyl to the U.S. ornamentals market in 2005. Bifenazate was first developed by Uniroyal Chemical in 1990 and commercialized by Crompton Corporation in 1999. Bifenazate was introduced to the ornamental market in 2010.

UsesHydramethylon is an insecticide primarily used in the form of baits for cockroaches and ants.

General DescriptionHydramethylnon appears as odorless yellow crystals. Insoluble in water. Used as an insecticide.

Preparation methods

PreparationHydramethylnon synthesis was achieved through the coupling in alcoholic media refluxing the compound 1,5-bis[p-(trifluoromethoxy)phenyl]-1,4-pentadien-3-one afforded the desired product in 50% yield.Synthesis of hydramethylnon

Upstream & downstream products

Upstream raw materials

Hexamethylenetetramine4-(Trifluoromethyl)benzaldehyde

Suppliers100 total

阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
湖北威德利化学试剂有限公司186-02735115 18062128043 · [email protected]
山东泰诚生物科技有限公司18769832557 18769832557 · [email protected]
深圳市星凯越生物科技有限公司0755-18589069862 18589069862 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
湖北鑫杰成化工科技有限公司13554075426 · [email protected]
温州共赢化学有限公司+86-0086-577-64498589 +86-15355981851 · [email protected]
陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]
湖北云镁科技有限公司027-59206672 18327059871 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
江苏豪隆化工有限公司0513-89083520 13328092525 · [email protected]
湖南瑞威尔生物科技有限公司18627957289 18173226957 · [email protected]
湖北威德利化学试剂有限公司17771473825 13385289472 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
湖北魏氏化学试剂股份有限公司027-59102966 18717199209 · [email protected]
上海艾梯西生物科技有限公司18721763493 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
玺标(上海)科技有限公司18512111473 18512111473 · [email protected]
上海毕楷科技有限公司18516304666 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
广东元丰化学试剂有限公司0751-2829979 13376591640 · [email protected]
武汉普洛夫生物科技有限公司17612776928 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
天津阿尔塔科技有限公司022-65378550-8551 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
康迪斯化工(湖北)有限公司13343438265 · [email protected]
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
湖北赛恩斯化工有限公司15994282563 15994282563 · [email protected]
海南瀚海致远生物科技有限公司18171012772 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
湖北威德利化学科技有限公司027-83989310 18627915365 · [email protected]
Henan Alfa Chemical Co., Ltd+8618339805032 · [email protected]
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
泰安嘉岳生物化工有限公司15318151873 · [email protected]
嘉兴市德亿化工有限公司0573-85866609 13325730825 · [email protected]
西安天广源生物科技有限公司+86-029-86333380 +86-18829239519 · [email protected]
湖北美钡新材料有限公司18271819653 · [email protected]
南京艾比克斯生化科技有限公司025-87193546 18652950785 · [email protected]
上海炎泽化工有限公司15345144255 19901447308 · [email protected]
湖北猫尔沃生物医药有限公司[email protected]
武汉市承天精细化工有限公司18164098996 · [email protected]
河北克拉维尔生物科技有限公司19930503252 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Hydramethylnon is a member of the class of hydrazones that is used as an insecticide for control of ants and cockroaches. It has a role as a mitochondrial cytochrome-bc1 complex inhibitor and an insecticide. It is a hydrazone, a member of pyrimidines, a member of (trifluoromethyl)benzenes, an olefinic compound and a member of guanidines.