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Home > Encyclopedia > Halofenozide

Halofenozide

Halofenozide structure

Halofenozide 

structure
  • CAS No:

    112226-61-6

  • Formula:

    C18H19ClN2O2

  • Chemical Name:

    Halofenozide

  • Synonyms:

    Benzoic acid,4-chloro-,2-benzoyl-2-(1,1-dimethylethyl)hydrazide;RH 0345;Halofenozide;Benzoic acid N-tert-butyl-N-(4-chlorobenzoyl)hydrazide;Spectrum Grub Stop Once & Done;Mach 2;Spectracide Grub Stop Once & Done;RG 100864;468062-58-0

  • Categories:

    Analytical Chemistry  >  Standard

Description

Halofenozide is a bisacylhydrazine insecticide and a member of monochlorobenzenes. It derives from a N'-benzoyl-N-(tert-butyl)benzohydrazide.

Halofenozide Basic Attributes

330.813

330.81

431-600-4

C81K20PELV

DTXSID4032619

White solid

29242990

Characteristics

49.4

3.22

0.38

>200 °C

1.584

In water, 12.3 ppm at 25 deg C

Store in a cool dry well-ventilated area. Prevent cross contamination with other pesticides, fertilizers, food, and feed. Store in original container and out of reach of children. Do not allow product to freeze. /MACH 2 2SC Insecticide/

4.07X10-10 mm Hg at 25 deg C (est)

Henry's Law constant = 3.58X10-11 atm-cu m/mol at 25 °C (est)

pKa = 1.40 (est)

Hydroxyl radical reaction rate constant = 2.4X10-11 cu cm/molec-sec at 25 °C (est)

Safety Information

III

9

3077

3

43-51/53

24-37-61

DG4976795

Xi,N

Stable to heat, light and water; hydrolysis DT50 310 days (pH 5), 481 days (pH 7), 226 days (pH 9).

P273-P280

H317-H411

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.|Triple rinse (or equivalent). then offer for recycling or reconditioning, or puncture and dispose of in a sanitary landfill, or by incineration, or , if allowed by State and local authorities, by burning. If burned, stay out of smoke. /MACH 2 2SC Insecticide/|Wastes resulting from the use of this product (that cannot be used according to label instructions) may be disposed of on site or at an approved waste disposal facility. /MACH 2 2SC Insecticide/|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 permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. 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 be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

|Warning|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P273, P280, P302+P352, P321, P333+P313, P363, P391, and P501|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|Aggregated GHS information provided by 194 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Applicators and other handlers who handle this pesticide for any use covered by the Worker Protection Standard (40 CFR 170) - in general, agricultural plant uses are covered - must wear: Long-sleeved shirt and long pants, waterproof gloves, shoes plus socks. /MACH 2 2SC Insecticide/|... Restricted-entry interval (REI) of 12 hours. Personal protective equipment (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, or water is: Coveralls. Waterproof gloves. Shoes plus socks. /MACH 2 2SC Insecticide/

Remain upwind. Avoid breathing smoke. Use water spray to cool containers exposed to fire. Contain run-off. /MACH 2 2SC Insecticide/|Firefighting equipment: Wear self-contained breathing apparatus (pressure demand NIOSH approved or equivalent) and full protective gear. /MACH 2 2SC Insecticide/|Use the following extinguishing media when fighting fires involving this material: carbon dioxide, dry chemical or water spray. /MACH 2 2SC Insecticide/

Pesticide particulates can become airborne. /MACH 2 2SC Insecticide/

Contain and absorb small spills with inert materials with sand or earth. Transfer liquids and solid diking material to separate suitable containers for recovery or disposal. Avoid breathing vapor. Keep spills and cleaning run-off out of municipal sewers and open bodies of water. ... If exposed to material during clean-up operations, remove all contaminated clothing promptly. Wash all exposed skin areas with soap and water immediately after exposure. Thoroughly lauder clothing before reuse. Do not take clothing home to be laundered. /MACH 2 2SC Insecticide/|Do not contaminate water when cleaning equipment or disposing of equipment washwaters. /MACH 2 2SC Insecticide/

Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR Part 170. /MACH 2 2SC Insecticide/|For terrestrial uses, do not apply directly to water or to areas where surface water is present or to intertidal areas below the mean high water mark. /MACH 2 2SC Insecticide/|Users should: Wash hands before eating, drinking, chewing gum, using tobacco or using the toilet. Remove contaminated clothing immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing. /MACH 2 2SC Insecticide/|Follow manufacturer's instructions for cleaning/maintaining personal protective equipment (PPE). If not such instructions for washables, use detergent and hot water. Keep and wash PPE separately from other laundry. /MACH 2 2SC Insecticide/|For more Preventive Measures (Complete) data for Halofenozide (7 total), please visit the HSDB record page.

SOURCE DOMINATED: Maximum and average concentrations of halofenozide applied at a rate of 1680 g/ha from August 1 through September 1 to Northeastern U.S. bentgrass greens and fairways in Boston, MA; Philadelphia, PA; and Rochester, NY were (max, ave; ug/cu m): 3.2X10-4, 9.2X10-6; 5.3X10-4, 1.6X10-6; and 4.3X10-4, 1.2X10-5, respectively(1).

Toxicity

LC50 Rat inhalation >2.7 mg/L/4 hr|LD50 Rabbit dermal >2000 mg/kg|LD50 Mouse oral 2214 mg/kg|LD50 Rat oral 2850 mg/kg

Halofenozide's production may result in its release to the environment through various waste streams; its use as an insecticide(1) in turfgrass management(2) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc range of 224 to 279(2) indicates that halofenozide is expected to have moderate mobility in soil(SRC). Volatilization of halofenozide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.6X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Halofenozide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.1X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Soil biodegradation half-lives ranging from 54 to 845 days(2) suggest that biodegradation is a variable environmental fate process in soil and may be strongly influenced by soil properties(SRC).|AQUATIC FATE: Based on a classification scheme(1), a Koc range of 224 to 279(2) indicates that halofenozide 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 3.6X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 62(SRC), from its log Kow of 3.22(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegradation data in water were not available(SRC, 2011).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), halofenozide, which has an estimated vapor pressure of 4.1X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase halofenozide may be removed from the air by wet or dry deposition(SRC). Halofenozide is stable to light(3) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Halofenozide is not expected to undergo hydrolysis in the environment based on half-lives of 310 days at pH 5, 481 days at pH 7, and 226 days at pH 9(1). Halofenozide is stable in light(1), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC). Photolysis half-live of 10 days in pond water and 129 days in soil have been reported(1). Overall soil dissipation half-lives in the field ranges from 42 to 267 days when applied to 5 different sites(1).

An estimated BCF of 62 was calculated in fish for halofenozide(SRC), using a log Kow of 3.22(1) and a regression-derived equation(2). Using a modeling approach based on the quantitative structure-activity relationship (QSAR), a log BCF of 1.6869, corresponding to a BCF of 49 was calculated(3). According to a classification scheme(4), these estimated BCF values suggest the potential for bioconcentration in aquatic organisms is moderate(SRC).

The Koc range of halofenozide is reported to be 224 to 279(1). According to a classification scheme(2), this Koc range suggests that halofenozide is expected to have moderate mobility in soil.

The Henry's Law constant for halofenozide is estimated as 3.6X10-11 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that halofenozide is expected to be essentially nonvolatile from water and moist soil surfaces(2). Halofenozide was applied at a rate of 1680 g/ha from August 1 through September 1 to Northeastern U.S. bentgrass greens and fairways in Boston, MA, Philadelphia, PA, and Rochester, NY in a study designed to assess inhalation health risk to golfers from turfgrass pesticides. Annual volatilization was 0.03, 0.04, and 0.02% of annual application, respectively(3). Halofenozide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.1X10-10 mm Hg(SRC), determined from a fragment constant method(4).

Occupational exposure to halofenozide may occur through inhalation and dermal contact with this compound at workplaces where halofenozide is produced or used(SRC). Limited monitoring data indicate that the general population may be exposed to halofenozide via inhalation of ambient air at golf courses(SRC). Halofenozide was applied at a rate of 1680 g/ha from August 1 through September 1 to Northeastern U.S. bentgrass greens and fairways in Boston, MA, Philadelphia, PA, and Rochester, NY in a study designed to assess inhalation health risk to golfers from turfgrass pesticides(1).

Drug Information

Pesticides 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. (See all compounds classified as Insecticides.)

Ecdysone agonist causing premature molting; insect growth regulator.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

halofenozide

Halofenozide Use and Manufacturing

Methods of Manufacturing

Preparation: R.W. Addor et al., EP 228564 (1987 to American Cyanamid)

Uses

Insecticide.

Granule; suspension concentrate.|Grub-B-Gon Granular Insecticide (The Scotts Company) Halofenozide 1%|Grubex (The Scotts Company) Halofenozide 1.5%|Mach 2 1.5g (Setre Chemical Co.) Halofenozide 1.5%|For more Formulations/Preparations (Complete) data for Halofenozide (13 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies halofenozide (technical grade) as Class III: slightly hazardous; Main Use: insecticide.

Determination of residues in soil by GC/NPD.

Computed Properties

Molecular Weight:330.8
XLogP3:3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:330.1135055
Monoisotopic Mass:330.1135055
Topological Polar Surface Area:49.4
Heavy Atom Count:23
Complexity:419
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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