Enilconazole

Last updated
Enilconazole
Enilconazole.svg
Imazalil 3D BS.png
Names
Preferred IUPAC name
1-{2-(2,4-Dichlorophenyl)-2-[(prop-2-en-1-yl)oxy]ethyl}-1H-imidazole
Other names
1-[2-(Allyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole
Imazalil
Chloramizole
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.047.817 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C14H14Cl2N2O/c1-2-7-19-14(9-18-6-5-17-10-18)12-4-3-11(15)8-13(12)16/h2-6,8,10,14H,1,7,9H2 Yes check.svgY
    Key: PZBPKYOVPCNPJY-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C14H14Cl2N2O/c1-2-7-19-14(9-18-6-5-17-10-18)12-4-3-11(15)8-13(12)16/h2-6,8,10,14H,1,7,9H2
    Key: PZBPKYOVPCNPJY-UHFFFAOYAI
  • Clc1ccc(c(Cl)c1)C(OCC=C)Cn2ccnc2
Properties
C14H14Cl2N2O
Molar mass 297.18 g·mol−1
AppearanceSlightly yellow to brown solidified oil [1]
Density 1.23 g/mL
Melting point 50 °C (122 °F; 323 K) [1]
Boiling point 347 °C (657 °F; 620 K) [2]
1400 mg/L (20 °C) [1]
Pharmacology
QD01AC90 ( WHO )
Hazards
Flash point 181 °C (358 °F; 454 K) [2]
Lethal dose or concentration (LD, LC):
227 mg/kg (oral rat)
4200 mg/kg (dermal, rabbit)
16 mg/l/4 h (inhalation, rat) [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Enilconazole (synonyms imazalil, chloramizole) is a fungicide widely used in agriculture, particularly in the growing of citrus fruits. [3] Trade names include Freshgard, Fungaflor, and Nuzone.

Contents

Enilconazole is also used in veterinary medicine as a topical antimycotic. [4]

History

In 1983, enilconazole was first introduced by Janssen Pharmaceutica and it has since consistently been registered as an antifungal postharvest agent. [5] Shortly after its introduction, enilconazole was used for seed treatment in 1984 and later used in chicken hatcheries in 1990. Like any fungicide, it was used to protect crops from becoming diseased and unable to yield a profitable harvest. Today, it continues to be utilized as an agricultural aid for its contribution to maintaining crop integrity and production output.[ citation needed ]

Use on crops

Enilconazole is found on a wide variety of fruits and vegetables, but it is primarily used on tubers for storage. [6] Common fungi that are attracted to tubers are Fusarium spp, Phoma spp, and Helminthosporium solani which depreciate the crop quality. [6] In 1984, when enilconazole was initially used for seed treatment, barley was a main target to mitigate crop loss due to disease. [6]

In addition, the antifungal agent is commonly used on citrus fruits. [3]

In the EU its use as a fungicide is permitted within some limits and imported fruits may contain limited amounts. [7]

Hazards

In 1999, based on studies in rodents, enilconazole was identified as "likely to be carcinogenic in humans" under The Environmental Protection Agency's Draft Guidelines for Carcinogenic Assessment. [5] However, because pesticide residues are well below the concentrations associated with risk, the lifetime cancer risk estimate associated with citrus fruit contamination was valued as insignificant. [5]

The EPA has established an equivalent toxicity level for human exposure at 6.1 x 10−2 mg/kg/day. This level placed it in Category I, II, and IV for oral, dermal, and inhalation toxicity. [5] Category I is classified as highly irritating to the eyes, but not to the skin. As for oral toxicity, when the fungicide is transferred via food into the body, it must be metabolized before it can do any damage.

Under California's Proposition 65, enilconazole is listed as "known to the State to cause cancer". [8]

The EPA determined there is no substantial risk of enilconazole toxicity through food and water exposure. Enilconazole has a very minute degree of mobility, so its level of drinking water contamination is quite low. The estimated environmental concentration (EEC) found the levels to be 0.072 ppb for surface water, which is much less than the 500 ppb comparison level for drinking water. [5]

Related Research Articles

Chlordane, or chlordan, is an organochlorine compound that was used as a pesticide. It is a white solid. In the United States, chlordane was used for termite-treatment of approximately 30 million homes until it was banned in 1988. Chlordane was banned 10 years earlier for food crops like corn and citrus, and on lawns and domestic gardens.

<span class="mw-page-title-main">Piperonyl butoxide</span> Chemical compound

Piperonyl butoxide (PBO) is a pale yellow to light brown liquid organic compound used as an adjuvant component of pesticide formulations for synergy. That is, despite having no pesticidal activity of its own, it enhances the potency of certain pesticides such as carbamates, pyrethrins, pyrethroids, and rotenone. It is a semisynthetic derivative of safrole and is produced from the condensation of the sodium salt of 2-(2-butoxyethoxy) ethanol and the chloromethyl derivative of hydrogenated safrole (dihydrosafrole); or through 1,2-Methylenedioxybenzene.

<span class="mw-page-title-main">Lindane</span> Organochlorine chemical and an isomer of hexachlorocyclohexane

Lindane, also known as gamma-hexachlorocyclohexane (γ-HCH), gammaxene, Gammallin and benzene hexachloride (BHC), is an organochlorine chemical and an isomer of hexachlorocyclohexane that has been used both as an agricultural insecticide and as a pharmaceutical treatment for lice and scabies.

<span class="mw-page-title-main">Dicofol</span> Chemical compound

Dicofol is an insecticide, an organochlorine that is chemically related to DDT. Dicofol is a miticide that is very effective against spider mite. Its production and use is banned internationally under the Stockholm Convention.

<span class="mw-page-title-main">Imidacloprid</span> Chemical compound

Imidacloprid is a systemic insecticide belonging to a class of chemicals called the neonicotinoids which act on the central nervous system of insects. The chemical works by interfering with the transmission of stimuli in the insect nervous system. Specifically, it causes a blockage of the nicotinergic neuronal pathway. By blocking nicotinic acetylcholine receptors, imidacloprid prevents acetylcholine from transmitting impulses between nerves, resulting in the insect's paralysis and eventual death. It is effective on contact and via stomach action. Because imidacloprid binds much more strongly to insect neuron receptors than to mammal neuron receptors, this insecticide is more toxic to insects than to mammals.

<span class="mw-page-title-main">Chlorpyrifos</span> Chemical compound

Chlorpyrifos (CPS), also known as chlorpyrifos ethyl, is an organophosphate pesticide that has been used on crops, and animals in buildings, and in other settings, to kill several pests, including insects and worms. It acts on the nervous systems of insects by inhibiting the acetylcholinesterase enzyme. Chlorpyrifos was patented in 1966 by Dow Chemical Company.

<span class="mw-page-title-main">Persistent organic pollutant</span> Organic compounds that are resistant to environmental degradation

Persistent organic pollutants (POPs) are organic compounds that are resistant to degradation through chemical, biological, and photolytic processes. They are toxic and adversely affect human health and the environment around the world. Because they can be transported by wind and water, most POPs generated in one country can and do affect people and wildlife far from where they are used and released.

<span class="mw-page-title-main">Vinclozolin</span> Fungicide used on fruits and vegetables

Vinclozolin is a common dicarboximide fungicide used to control diseases, such as blights, rots and molds in vineyards, and on fruits and vegetables such as raspberries, lettuce, kiwi, snap beans, and onions. It is also used on turf on golf courses. Two common fungi that vinclozolin is used to protect crops against are Botrytis cinerea and Sclerotinia sclerotiorum. First registered in 1981, vinclozolin is widely used but its overall application has declined. As a pesticide, vinclozolin is regulated by the United States Environmental Protection Agency. In addition to these restrictions within the United States, as of 2006 the use of this pesticide was banned in several countries, including Denmark, Finland, Norway, and Sweden. It has gone through a series of tests and regulations in order to evaluate the risks and hazards to the environment and animals. Among the research, a main finding is that vinclozolin has been shown to be an endocrine disruptor with antiandrogenic effects.

<span class="mw-page-title-main">Fipronil</span> Chemical compound

Fipronil is a broad-spectrum insecticide that belongs to the phenylpyrazole chemical family. Fipronil disrupts the insect central nervous system by blocking the ligand-gated ion channel of the GABAA receptor and glutamate-gated chloride (GluCl) channels. This causes hyperexcitation of contaminated insects' nerves and muscles. Fipronil's specificity towards insects is believed to be due to its greater binding affinity for the GABAA receptors of insects than to those of mammals, and for its action on GluCl channels, which do not exist in mammals. As of 2017, there does not appear to be significant resistance among fleas to fipronil.

Pesticide residue refers to the pesticides that may remain on or in food, after they are applied to food crops. The maximum allowable levels of these residues in foods are stipulated by regulatory bodies in many countries. Regulations such as pre-harvest intervals also prevent harvest of crop or livestock products if recently treated in order to allow residue concentrations to decrease over time to safe levels before harvest.

<span class="mw-page-title-main">Chlorothalonil</span> Fungicide

Chlorothalonil (2,4,5,6-tetrachloroisophthalonitrile) is an organic compound mainly used as a broad spectrum, nonsystemic fungicide, with other uses as a wood protectant, pesticide, acaricide, and to control mold, mildew, bacteria, algae. Chlorothalonil-containing products are sold under the names Bravo, Echo, and Daconil. It was first registered for use in the US in 1966. In 1997, it was the third most used fungicide in the US, behind only sulfur and copper, with 12 million pounds used in agriculture that year. Including nonagricultural uses, the United States Environmental Protection Agency (EPA) estimates, on average, almost 15 million lb (6.8 million kg) were used annually from 1990 to 1996.

<span class="mw-page-title-main">Soil contamination</span> Pollution of land by human-made chemicals or other alteration

Soil contamination, soil pollution, or land pollution as a part of land degradation is caused by the presence of xenobiotic (human-made) chemicals or other alteration in the natural soil environment. It is typically caused by industrial activity, agricultural chemicals or improper disposal of waste. The most common chemicals involved are petroleum hydrocarbons, polynuclear aromatic hydrocarbons, solvents, pesticides, lead, and other heavy metals. Contamination is correlated with the degree of industrialization and intensity of chemical substance. The concern over soil contamination stems primarily from health risks, from direct contact with the contaminated soil, vapour from the contaminants, or from secondary contamination of water supplies within and underlying the soil. Mapping of contaminated soil sites and the resulting clean ups are time-consuming and expensive tasks, and require expertise in geology, hydrology, chemistry, computer modelling, and GIS in Environmental Contamination, as well as an appreciation of the history of industrial chemistry.

<span class="mw-page-title-main">Methoxychlor</span> Synthetic organochloride insecticide, now obsolete.

Methoxychlor is a synthetic organochloride insecticide, now obsolete. Tradenames for methoxychlor include Chemform, Maralate, Methoxo, Methoxcide, Metox, and Moxie.

<span class="mw-page-title-main">Dimethoate</span> Chemical compound

Dimethoate is a widely used organophosphate insecticide and acaricide. It was patented and introduced in the 1950s by American Cyanamid. Like other organophosphates, dimethoate is an acetylcholinesterase inhibitor which disables cholinesterase, an enzyme essential for central nervous system function. It acts both by contact and through ingestion. It is readily absorbed and distributed throughout plant tissues, and is degraded relatively rapidly. One of the breakdown products of dimethoate is omethoate, a potent cholinesterase inhibitor, is ten times more toxic than its parent compound.

<span class="mw-page-title-main">Azoxystrobin</span> Chemical compound

Azoxystrobin is a broad spectrum systemic fungicide widely used in agriculture to protect crops from fungal diseases. It was first marketed in 1996 using the brand name Amistar and by 1999 it had been registered in 48 countries on more than 50 crops. In the year 2000 it was announced that it had been granted UK Millennium product status.

<span class="mw-page-title-main">Clothianidin</span> Chemical compound

Clothianidin is an insecticide developed by Takeda Chemical Industries and Bayer AG. Similar to thiamethoxam and imidacloprid, it is a neonicotinoid. Neonicotinoids are a class of insecticides that are chemically similar to nicotine, which has been used as a pesticide since the late 1700s. Clothianidin and other neonicotinoids act on the central nervous system of insects as an agonist of nAChR, the same receptor as acetylcholine, the neurotransmitter that stimulates and activating post-synaptic acetylcholine receptors but not inhibiting AChE. Clothianidin and other neonicotinoids were developed to last longer than nicotine, which is more toxic and which breaks down too quickly in the environment.

<span class="mw-page-title-main">Chlormequat</span> Chemical compound

Chlormequat is an organic compound with the formula ClCH
2
CH
2
N(CH
3
)+
3
that is used as a plant growth regulator. It is typically sold as the chloride salt, chlormequat chloride (C5H13Cl2N), a colorless hygroscopic crystalline substance that is soluble in water and ethanol. It is an alkylating agent and a quaternary ammonium salt. Chlormequat is one of the onium-type growth regulators.

<span class="mw-page-title-main">Cyproconazole</span> Chemical compound

Cyproconazole is an agricultural fungicide of the class of azoles, used on cereal crops, coffee, sugar beet, fruit trees and grapes, and peanuts, on sod farms and golf course turf and on wood as a preservative. It has been used against powdery mildew, rust on cereals and apple scab, and applied by air or on the ground or by chemigation.

<i>Penicillium digitatum</i> Species of fungus

Penicillium digitatum is a mesophilic fungus found in the soil of citrus-producing areas. It is a major source of post-harvest decay in fruits and is responsible for the widespread post-harvest disease in Citrus fruit known as green rot or green mould. In nature, this necrotrophic wound pathogen grows in filaments and reproduces asexually through the production of conidiophores and conidia. However, P. digitatum can also be cultivated in the laboratory setting. Alongside its pathogenic life cycle, P. digitatum is also involved in other human, animal and plant interactions and is currently being used in the production of immunologically based mycological detection assays for the food industry.

<span class="mw-page-title-main">Butylate (herbicide)</span> Weed control herbicide

Butylate or butilate is a widely used thiocarbamate herbicide. As a herbicide, it was introduced in 1962, and it quickly became the fourth most used herbicide in the US, with 28.5 million pounds used in 1974. Its use has declined significantly, to 15 million pounds in 1991 to 950 thousand pounds by 1998. It is used on corn, to control grassy and broadleaf weeds and nutsedge.

References

  1. 1 2 3 "Pesticide Information Profile: Imazalil". Extension Toxicology Network.
  2. 1 2 3 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. 1 2 Kaplan, H. J.; Dave, B. A. (1979). "The current status of Imazalil: a post harvest fungicide for citrus". Proceedings of the Florida State Horticultural Society. 92: 37–43.
  4. EMA Committee for Veterinary Products: Enilconazole
  5. 1 2 3 4 5 "R.E.D. Facts: Imazalil" (PDF). Environmental Protection Agency. February 2005.{{cite journal}}: Cite journal requires |journal= (help)
  6. 1 2 3 "Imazalil". Certis Europe. Archived from the original on 2018-04-05. Retrieved 2013-04-18.
  7. Commission Regulation (EU) 2019/1582 of 25 September 2019 amending Annexes II and III to Regulation (EC) No 396/2005 of the European Parliament and of the Council as regards maximum residue levels for imazalil in or on certain products
  8. Proposition 65 Archived 2019-07-29 at the Wayback Machine , Office of Environmental Health Hazard Assessment