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Hydramethylnon (Tetrahydro-5,5-dimethyl- 2(1H)pyrimidinone[3-[4-(trifluoromethyl)phenyl]-1-[2- [4(trifluoromethyl) phenyl]ethenyl]-2 propenylidene]hydrazone)(CAS No. 67485-29-4)

Hydramethylnon (Tetrahydro-5,5-dimethyl- 2(1H)pyrimidinone[3-[4-(trifluoromethyl)phenyl]-1-[2- [4(trifluoromethyl) phenyl]ethenyl]-2 propenylidene]hydrazone) C25H24F6N4 (cas 67485-29-4) Molecular Structure

67485-29-4 Structure

Identification and Related Records

Hydramethylnon (Tetrahydro-5,5-dimethyl- 2(1H)pyrimidinone[3-[4-(trifluoromethyl)phenyl]-1-[2- [4(trifluoromethyl) phenyl]ethenyl]-2 propenylidene]hydrazone)
【CAS Registry number】
AC 217300
2(1H)-Pyrimidinone,tetrahydro-5,5-dimethyl-,[3-[4-(trifluoromethyl)phenyl]-1-[2-[4- (trifluoromethyl)phenyl]ethenyl]-2-propenylidene] hydrazone
CL 217300
Hydramethylnon 95%TC
【Molecular Formula】
C25H24F6N4 (Products with the same molecular formula)
【Molecular Weight】
【Canonical SMILES】
【Isomers smiles】
【MOL File】

Chemical and Physical Properties

Odorless yellow crystals.
【Melting Point】
【Boiling Point】
510.5°C at 760 mmHg
【Refractive Index】
【Flash Point】
0.006 mg/L @ 25 C
Yellowish oily liquid
No data.
【Storage temp】
【Spectral properties】
Index of refraction: 1.618-1.623 at 20 deg C/D
【Computed Properties】
Molecular Weight:132.15922 [g/mol]
Molecular Formula:C9H8O
H-Bond Donor:0
H-Bond Acceptor:1
Rotatable Bond Count:2
Exact Mass:132.057515
MonoIsotopic Mass:132.057515
Topological Polar Surface Area:17.1
Heavy Atom Count:10
Formal Charge:0
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:1
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Ring Count:1
Effective Rotor Count:2
Conformer Sampling RMSD:0.4
CID Conformer Count:2

Safety and Handling

【Hazard Codes】
【Risk Statements】
【Safety Statements 】

Moderately toxic by ingestion. Low toxicity by inhalation and skin contact routes. When heated to decomposition it emits toxic vapors of NOx and F.
Safety information of Hydramethylnon (67485-29-4):
Hazard Codes  T;N
Risk Statements  22-36-48/25-50/53
R22: Harmful if swallowed
R36: Causes burns
R48/25: Toxic: danger of serious damage to health by prolonged exposure if swallowed
R50/53: Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment 
Safety Statements  1/2-22-26-36/37-45-60-61
S1/2: Keep locked up and out of the reach of children
S22: Do not breathe dust
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37: Wear suitable protective clothing and gloves
S45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
S60: This material and/or its container must be disposed of as hazardous waste
S61: Avoid release to the environment. Refer to special instructions safety data sheet
RIDADR  UN3077 9/PG 3

【Skin, Eye, and Respiratory Irritations】
Primary eye irritant ... Dermal irritant.
No primary dermal irritation was observed in human subjects exposed for 48 hours to a solution of a 3% active ingredient, while severe primary dermal irritation was observed in human subjects after exposure to 8% active ingredient.
【Cleanup Methods】
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal.
Do not contaminate water by cleaning of equipment or disposal of wastes. /Cinnacure A3005/
UN3077 9/PG 3
【Fire Fighting Procedures】
CO2, dry chemical, or appropriate foam.
Perfume grade, FCC, 98% min purity.
Chief ingredient (up to 90%) of oil of cinnamon.
Cinnacure A3005; Active ingredient 30.00% Cinnamaldehyde
Cinnacure Ready to Use; Active ingredient 0.255% Cinnamaldehyde
【Exposure Standards and Regulations】
Synthetic flavoring substances and adjuvants /for human consumption/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Cinnamaldehyde is included on this list.
Synthetic flavoring substances and adjuvants /for animal drugs, feeds, and related products/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Cinnamaldehyde is included on this list.
【Reactivities and Incompatibilities】
Rags soaked in sodium hydroxide and in /cinnamaldehyde/ overheated and ignited owing to aerobic oxidation when they came into contact in a waste bin.
【Other Preventative Measures】
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
User should: Wash hands before eating, drinking, chewing gum, using tobacco or using the toilet. Remove clothing immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing. /Cinnacure A3005/
Agricultural use requirements. Use this product only in accordance with its labeling and with Worker Protection Standard, 40 CFR part 170. ... Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of 4 hours. /Cinnacure A3005/
Do not apply directly to water, or to areas where surface water is present or to intertidal areas below the nean high water mark. /Cinnacure A3005/
【Protective Equipment and Clothing】
Agricultural use requirements. PPE required for early entry to treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated, such as plants, soil, water, is: Coveralls, waterproof gloves, shoes plus socks./Cinnacure A3005/
Long-sleeved shirt and long pants, protective eyewear, shoes plus socks, waterproof gloves.
【Octanol/Water Partition Coefficient】
log Kow = 1.90
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Do not use, pour, spill or store near heat or open flame. /Cinnacure A3005/

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

For the synthesis, only the base-catalyzed condensation of benzaldehyde with acetaldehyde has been adopted on an industrial scale.
Cinnamaldehyde has been efficiently isolated in high purity by fractional distillation from cassia and cinnamon bark essential oils.
Preparation by condensation of benzaldehyde and acetaldehyde.
... Oxidation of cinnamyl alcohol
U.S. Imports

(1972) 1.85X10+7 G (CINNAMON OIL)
(1975) 1.9X10+7 G (OIL)
U.S. Production

(1972) 7.11X10+8 G
(1973) 8.0X10+8 GRAMS
2-Propenal, 3-phenyl- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 1986 >1 million - 10 million 1990 >1 million - 10 million 1994 >1 million - 10 million 1998 >1 million - 10 million 2002 >1 million - 10 million
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 2006 1 to <10 million lbs
Consumption Patterns

Greater than 95% of the consumption of cinnamaldehyde occurs in flavor applications where a spicy, cinnamon character is required.
Slow-acting insecticide for ants (big headed, fire, harvester).

Biomedical Effects and Toxicity

【Pharmacological Action】
- Agents that reduce the frequency or rate of spontaneous or induced mutations independently of the mechanism involved.
- Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.
- Substances added to foods and medicine to improve the quality of taste.
【Therapeutic Uses】
/EXPL THER/ Cinnamonum zeylanicum (cinnamon) is widely used in traditional system of medicine to treat diabetes in India. The present study was carried out to isolate and identify the putative antidiabetic compounds ... Cinnamaldehyde was administered at different doses (5, 10 and 20 mg/kg bw) for 45 days to streptozotocin (STZ) (60 mg/kg bw)-induced male diabetic wistar rats. It was found that plasma glucose concentration was significantly (p<0.05) decreased in a dose-dependent manner (63.29%) compared to the control. In addition, oral administration of cinnamaldehyde (20 mg/kg bw) significantly decreased glycosylated hemoglobin (HbA(1C)), serum total cholesterol, triglyceride levels and at the same time markedly increased plasma insulin, hepatic glycogen and high-density lipoprotein-cholesterol levels. Also cinnamaldehyde restored the altered plasma enzyme (aspartate aminotransferase, alanine aminotransferase, lactate dehydrogenase, alkaline phosphatase and acid phosphatase) levels to near normal. Administration of glibenclamide, a reference drug (0.6 mg/kg bw) also produced a significant (p < 0.05) reduction in blood glucose concentration in STZ-induced diabetic rats. The results of this experimental study indicate that cinnamaldehyde possesses hypoglycemic and hypolipidemic effects in STZ-induced diabetic rats. [Subash BP et al; Phytomedicine 14 (1): 15-22 (2007). Available from, as of July 14, 2009:]
【Biomedical Effects and Toxicity】
The bioavailability of microencapsulated cinnamaldehyde (CNMA) was investigated in male F344 rats. Rats were gavaged with CNMA in corn oil using either microencapsulated or the neat chemical at doses of 50, 250, and 500 mg/kg. No differences between the two formulations at any of the doses were found in either CNMA blood concentration profiles or in the rate of urinary hippuric acid excretion. Both formulations showed a low bioavailability (PubMed Abstract
/Cinnamaldehyde is/ presumably oxidized in vivo to cinnamic acid, which is excreted in urine as benzoic and hippuric acids.
After ip admin of cinnamic aldehyde to rats, urinary thio ether excretion amounted to 6.5% of dose.
Cinnamaldehyde administered intraperitoneally to a rabbit was excreted in the urine as cinnamic acid, cinnamoylglycine, benzoic acid and hippuric acid.
Once formed, cinnamyl alcohol, cinnamaldehyde and cinnamic acid have all been shown to be rapidly absorbed from the gut, metabolized and excreted primarily in the urine and, to a minor extent, in the feces. Results of numerous studies indicate that cinnamyl derivatives are absorbed, metabolized and excreted as polar metabolites within 24 hr. [Adams TB et al; Food and Chem Toxicol 42: 157-185 (2004). Available from, as of July 14, 2009:] PubMed Abstract
In a study of tissue distribution and excretion of cinnamaldehyde, male F344 rats (8/ group) were pretreated with single daily oral doses of 5, 50, or 500 mg/kg bw of cinnamaldehyde by gavage for 7 days. Twenty-four hours later, animals in each group received a single oral dose of [3-(14)C]cinnamaldehyde equivalent to the pretreatment level. Groups of rats (8/ group) receiving no pretreatment were also given single oral doses of 5, 50 or 500 mg/kg bw. Radioactivity is distributed primarily to the gastrointestinal tract, kidneys, and liver, after single- or multiple-dose oral administration. After 24 hr, >80% of the radioactivity is recovered in the urine and PubMed Abstract
In a study of the effect of dose, species, and sex on the disposition of [3-(14)C]cinnamaldehyde. A 2.0 or 250 mg/kg bw dose of cinnamaldehyde was administered to groups of male and female F344 rats (4/group) or CD1 mice (6/group) by intraperitoneal injection. Regardless of the dose level, species, or sex, greater than 85% of the radiolabel is recovered in the urine and feces within 24 hr. Greater than 90% is recovered after 72 hr. When 250 mg/kg bw of [3-(14)C]cinnamaldehyde is administered orally to F344 rats, 98% is recovered from the urine (91%) and feces (7%) within 24 hr. [Adams TB et al; Food and Chem Toxicol 42: 157-185 (2004). Available from, as of July 14, 2009:] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 37(SRC), determined from a log Kow of 1.9(2) and a regression-derived equation(3), indicates that cinnamaldehyde is expected to have very high mobility in soil(SRC). Volatilization of cinnamaldehyde from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 3.5X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 2.89X10-2 mm Hg(4), and water solubility, 1,420 mg/L(5). Cinnamaldehyde is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Biodegradation data were not available(SRC, 2009).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 37(SRC), determined from a log Kow of 1.9(2) and a regression-derived equation(3), indicates that cinnamaldehyde is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 3.5X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 2.89X10-2 mm Hg(4), and water solubility, 1,420 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 290 hours and 91 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 8(SRC), from its log Kow (2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2009).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cinnamaldehyde, which has a vapor pressure of 2.89X10-2 mm Hg at 25 deg C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase cinnamaldehyde 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 10 hours and 9.5 hours for the cis- and trans-isomers, respectively(SRC), calculated from its rate constant of 3.8X10-11 and 4.0X10-11 cu cm/molecule-sec at 25 deg C for cis- and trans-isomers, respectively(SRC). Cinnamaldehyde does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

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