Acetochlor

Last updated
Acetochlor [1]
Acetochlor.png
Names
Preferred IUPAC name
2-Chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methylphenyl)acetamide
Other names
Azetochlor
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.047.166 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C14H20ClNO2/c1-4-12-8-6-7-11(3)14(12)16(10-18-5-2)13(17)9-15/h6-8H,4-5,9-10H2,1-3H3 Yes check.svgY
    Key: VTNQPKFIQCLBDU-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C14H20ClNO2/c1-4-12-8-6-7-11(3)14(12)16(10-18-5-2)13(17)9-15/h6-8H,4-5,9-10H2,1-3H3
    Key: VTNQPKFIQCLBDU-UHFFFAOYAJ
  • ClCC(=O)N(c1c(cccc1CC)C)COCC
Properties
C14H20ClNO2
Molar mass 269.77 g·mol−1
Density 1.100 at 30 °C
1.136 at 20 °C
Melting point <0 °C (32 °F; 273 K)
223 ppm
Hazards
Flash point >100 °C (212 °F; 373 K)
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 ?)

Acetochlor is an herbicide developed by Monsanto Company and Zeneca. It is a member of the class of herbicides known as chloroacetanilides. Its mode of action is elongase inhibition, and inhibition of geranylgeranyl pyrophosphate (GGPP) cyclization enzymes, part of the gibberellin pathway. It carries high risks of environmental contamination. [2]

Contents

Uses

In the United States, acetochlor was registered by the EPA as a direct substitute for many herbicides of known concern. The EPA imposed several restrictions and conditions on the use of acetochlor. [3]

It is approved for pre-emergence application or for pre-planting application with soil incorporation, in corn. (maize) at 5 litres / hectare (1835g / hectare of a.i.) [4] It is the main active ingredient in Acenit, Keystone, Guardian, Harness, Relay, Sacemid, Surpass, Top-Hand, Trophy and Winner.

It is used to control weeds in corn, and is particularly useful as a replacement for atrazine in the case of some important weeds.

Safety

Acetochlor has been classified as a probable human carcinogen. [1] [3] Acetochlor, as alachlor, can cause nasal turbinate tumors via the generation of a common tissue reactive metabolite that leads to cytotoxicity and regenerative proliferation in the nasal epithelium. [5]

It is a thyroid disruptor. [6] [ non-primary source needed ]

Human health effects from acetochlor at low environmental doses or at biomonitored levels from low environmental exposures are unknown. [7] A case of poisoning with extremely swollen genitals as a symptom was reported after contact. [8]

Ecologic effects

In the United States, acetochlor is the third most frequently detected herbicide in natural waters. [9]

Acetochlor can accelerate metamorphosis in amphibians. [10] It can also affect the development of fish. [10]

See also

Related Research Articles

<span class="mw-page-title-main">Pesticide</span> Substance used to destroy pests

Pesticides are substances that are used to control pests. They include herbicides, insecticides, nematicides, fungicides, and many others. The most common of these are herbicides, which account for approximately 50% of all pesticide use globally. Most pesticides are used as plant protection products, which in general protect plants from weeds, fungi, or insects. In general, a pesticide is a chemical or biological agent that deters, incapacitates, kills, or otherwise discourages pests. Target pests can include insects, plant pathogens, weeds, molluscs, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, or spread disease, or are disease vectors. Along with these benefits, pesticides also have drawbacks, such as potential toxicity to humans and other species.

Roundup is a brand name of herbicide originally produced by Monsanto, which Bayer acquired in 2018. Prior to the late-2010s formulations, it used broad-spectrum glyphosate-based herbicides. As of 2009, sales of Roundup herbicides still represented about 10 percent of Monsanto's revenue despite competition from Chinese producers of other glyphosate-based herbicides. The overall Roundup line of products represented about half of Monsanto's yearly revenue in 2009. The product is marketed to consumers by Scotts Miracle-Gro Company. In the late-2010s other non-glyphosate containing herbicides were also sold under the Roundup brand.

<span class="mw-page-title-main">Glyphosate</span> Systemic herbicide and crop desiccant

Glyphosate is a broad-spectrum systemic herbicide and crop desiccant. It is an organophosphorus compound, specifically a phosphonate, which acts by inhibiting the plant enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSP). It is used to kill weeds, especially annual broadleaf weeds and grasses that compete with crops. Its herbicidal effectiveness was discovered by Monsanto chemist John E. Franz in 1970. Monsanto brought it to market for agricultural use in 1974 under the trade name Roundup. Monsanto's last commercially relevant United States patent expired in 2000.

<span class="mw-page-title-main">Pesticide poisoning</span> Poisoning of humans from pesticide exposure

A pesticide poisoning occurs when pesticides, chemicals intended to control a pest, affect non-target organisms such as humans, wildlife, plants, or bees. There are three types of pesticide poisoning. The first of the three is a single and short-term very high level of exposure which can be experienced by individuals who commit suicide, as well as pesticide formulators. The second type of poisoning is long-term high-level exposure, which can occur in pesticide formulators and manufacturers. The third type of poisoning is a long-term low-level exposure, which individuals are exposed to from sources such as pesticide residues in food as well as contact with pesticide residues in the air, water, soil, sediment, food materials, plants and animals.

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

In organic chemistry, chlorpyrifos (CPS), also known as chlorpyrifos ethyl, is an organophosphate pesticide that has been used on crops, animals, and 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">Endocrine disruptor</span> Chemicals that can interfere with endocrine or hormonal systems

Endocrine disruptors, sometimes also referred to as hormonally active agents, endocrine disrupting chemicals, or endocrine disrupting compounds are chemicals that can interfere with endocrine systems. These disruptions can cause numerous adverse human health outcomes including, alterations in sperm quality and fertility, abnormalities in sex organs, endometriosis, early puberty, altered nervous system function, immune function, certain cancers, respiratory problems, metabolic issues, diabetes, obesity, cardiovascular problems, growth, neurological and learning disabilities, and more. Found in many household and industrial products, endocrine disruptors "interfere with the synthesis, secretion, transport, binding, action, or elimination of natural hormones in the body that are responsible for development, behavior, fertility, and maintenance of homeostasis ."

<span class="mw-page-title-main">Paraquat</span> Chemical compound used as an herbicide

Paraquat (trivial name; ), or N,N′-dimethyl-4,4′-bipyridinium dichloride (systematic name), also known as methyl viologen, is an organic compound with the chemical formula [(C6H7N)2]Cl2. It is classified as a viologen, a family of redox-active heterocycles of similar structure. This salt is one of the most widely used herbicides. It is quick-acting and non-selective, killing green plant tissue on contact. It is also toxic (lethal) to human beings and animals due to its redox activity, which produces superoxide anions. It has been linked to the development of Parkinson's disease and is banned in 58 countries.

<span class="mw-page-title-main">Alachlor</span> Chemical compound; herbicide

Alachlor is an herbicide from the chloroacetanilide family. It is an odorless, white solid. The greatest use of alachlor is for control of annual grasses and broadleaf weeds in crops. Use of alachlor is illegal in the European Union and no products containing alachlor are currently registered in the United States.

<span class="mw-page-title-main">Atrazine</span> Herbicide

Atrazine is a chlorinated herbicide of the triazine class. It is used to prevent pre-emergence broadleaf weeds in crops such as maize (corn), soybean and sugarcane and on turf, such as golf courses and residential lawns. Atrazine's primary manufacturer is Syngenta and it is one of the most widely used herbicides in the United States, Canadian, and Australian agriculture. Its use was banned in the European Union in 2004, when the EU found groundwater levels exceeding the limits set by regulators, and Syngenta could not show that this could be prevented nor that these levels were safe.

<span class="mw-page-title-main">Dicamba</span> Chemical compound used as herbicide

Dicamba is a selective systemic herbicide first registered in 1967. Brand names for formulations of this herbicide include Dianat, Banvel, Diablo, Oracle and Vanquish. This chemical compound is a chlorinated derivative of o-anisic acid. It has been described as a "widely used, low-cost, environmentally friendly herbicide that does not persist in soils and shows little or no toxicity to wildlife and humans."

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

Metolachlor is an organic compound that is widely used as an herbicide. It is a derivative of aniline and is a member of the chloroacetanilide family of herbicides. It is highly effective toward grasses.

<span class="mw-page-title-main">Organophosphate poisoning</span> Toxic effect of pesticides

Organophosphate poisoning is poisoning due to organophosphates (OPs). Organophosphates are used as insecticides, medications, and nerve agents. Symptoms include increased saliva and tear production, diarrhea, vomiting, small pupils, sweating, muscle tremors, and confusion. While onset of symptoms is often within minutes to hours, some symptoms can take weeks to appear. Symptoms can last for days to weeks.

<span class="mw-page-title-main">Environmental toxicology</span>

Environmental toxicology is a multidisciplinary field of science concerned with the study of the harmful effects of various chemical, biological and physical agents on living organisms. Ecotoxicology is a subdiscipline of environmental toxicology concerned with studying the harmful effects of toxicants at the population and ecosystem levels.

<span class="mw-page-title-main">Pesticide drift</span> Diffusion of pesticides into the environment

Pesticide drift, also known as spray drift refers to the unintentional diffusion of pesticides toward nontarget species. It is one of the most negative effects of pesticide application. Drift can damage human health, environment, and crops. Together with runoff and leaching, drift is a mechanism for agricultural pollution. Some drift results from contamination of sprayer tanks.

<span class="mw-page-title-main">Environmental impact of pesticides</span> Environmental effect

The environmental effects of pesticides describe the broad series of consequences of using pesticides. The unintended consequences of pesticides is one of the main drivers of the negative impact of modern industrial agriculture on the environment. Pesticides, because they are toxic chemicals meant to kill pest species, can affect non-target species, such as plants, animals and humans. Over 98% of sprayed insecticides and 95% of herbicides reach a destination other than their target species, because they are sprayed or spread across entire agricultural fields. Other agrochemicals, such as fertilizers, can also have negative effects on the environment.

<span class="mw-page-title-main">Health effects of pesticides</span> How pesticides affect human health

Health effects of pesticides may be acute or delayed in those who are exposed. Acute effects can include pesticide poisoning, which may be a medical emergency. Strong evidence exists for other, long-term negative health outcomes from pesticide exposure including birth defects, fetal death, neurodevelopmental disorder, cancer, and neurologic illness including Parkinson's disease. Toxicity of pesticides depend on the type of chemical, route of exposure, dosage, and timing of exposure.

Xenohormones or environmental hormones are compounds produced outside of the human body which exhibit endocrine hormone-like properties. They may be either of natural origin, such as phytoestrogens, which are derived from plants, or of synthetic origin. These compounds can cause endocrine disruption by multiple mechanisms including acting directly on hormone receptors, affecting the levels of natural hormones in the body, and by altering the expression of hormone receptors. The most commonly occurring xenohormones are xenoestrogens, which mimic the effects of estrogen. Other xenohormones include xenoandrogens and xenoprogesterones. Xenohormones are used for a variety of purposes including contraceptive & hormonal therapies, and agriculture. However, exposure to certain xenohormones early in childhood development can lead to a host of developmental issues including infertility, thyroid complications, and early onset of puberty. Exposure to others later in life has been linked to increased risks of testicular, prostate, ovarian, and uterine cancers.

<span class="mw-page-title-main">2,4-Dichlorophenoxyacetic acid</span> Herbicide

2,4-Dichlorophenoxyacetic acid is an organic compound with the chemical formula Cl2C6H3OCH2CO2H. It is usually referred to by its ISO common name 2,4-D. It is a systemic herbicide that kills most broadleaf weeds by causing uncontrolled growth, but most grasses such as cereals, lawn turf, and grassland are relatively unaffected.

Glyphosate-based herbicides are usually made of a glyphosate salt that is combined with other ingredients that are needed to stabilize the herbicide formula and allow penetration into plants. The glyphosate-based herbicide Roundup was first developed by Monsanto in the 1970s. It is used most heavily on corn, soy, and cotton crops that have been genetically modified to be resistant to the herbicide. Some products include two active ingredients, such as Enlist Duo which includes 2,4-D as well as glyphosate. As of 2010, more than 750 glyphosate products were on the market. The names of inert ingredients used in glyphosate formulations are usually not listed on the product labels.

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

Cyanazine is a herbicide that belongs to the group of triazines. Cyanazine inhibits photosynthesis and is therefore used as a herbicide.

References

  1. 1 2 Cornell University Extension Toxicology Network Pesticide Information Profile on Acetochlor
  2. Arregui, M.; Sánchez, D.; Althaus, R.; Scotta, R.; Bertolaccini, I. (2010). "Assessing the risk of pesticide environmental impact in several Argentinian cropping systems with a fuzzy expert indicator". Pest Management Science. 66 (7): 736–740. doi:10.1002/ps.1935. PMID   20232283.
  3. 1 2 "Acetochlor". EPA. Retrieved 2 April 2010.
  4. "e-phy". agriculture.gouv.fr. Retrieved 17 May 2015.
  5. "Cumulative Risk Assessment for the Chloroacetanilides" (PDF). EPA. 2006-03-29. Retrieved 2 April 2010.
  6. Turque, N.; Palmier, K.; Le Mével, S.; Alliot, C.; Demeneix, B. A. (2005). "A Rapid, Physiologic Protocol for Testing Transcriptional Effects of Thyroid-Disrupting Agents in Premetamorphic Xenopus Tadpoles". Environmental Health Perspectives. 113 (11): 1588–1593. doi:10.1289/ehp.7992. PMC   1310923 . PMID   16263516.
  7. "National Report on Human Exposure to Environmental Chemicals". CDC. 11 February 2010. Archived from the original on 5 June 2011. Retrieved 2 April 2010.
  8. Tian, Runhui; Liu, Lingyun; Liang, Zuowen; Guo, Kaimin (2019). "Acetochlor poisoning presenting as acute genital edema: A case report". Urology Case Reports. 22: 47–48. doi:10.1016/j.eucr.2018.10.014. PMC   6214889 . PMID   30406020.
  9. Foley, M.; Sigler, V.; Gruden, C. (2008). "A multiphasic characterization of the impact of the herbicide acetochlor on freshwater bacterial communities". The ISME Journal. 2 (1): 56–66. doi: 10.1038/ismej.2007.99 . PMID   18180747.
  10. 1 2 Li, W.; Zha, J.; Li, Z.; Yang, L.; Wang, Z. (2009). "Effects of exposure to acetochlor on the expression of thyroid hormone related genes in larval and adult rare minnow (Gobiocypris rarus)". Aquatic Toxicology. 94 (2): 87–93. doi:10.1016/j.aquatox.2009.06.002. PMID   19577311.