Names | |
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Preferred IUPAC name 2-Chloro-N-(ethoxymethyl)-N-(2-ethyl-6-methylphenyl)acetamide | |
Other names Azetochlor CP55097 ICIA-5676 | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.047.166 |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
| |
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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). |
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]
Acetochlor is manufactured in two steps from 2-ethyl-6-methylaniline. A reaction with chloroacetyl chloride gives an anilide which is treated with chloromethyl ethyl ether and sodium hydroxide to form the herbicide. [3]
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. [4]
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.) [5] 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.
Acetochlor has been classified as a probable human carcinogen. [1] [4] 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. [6]
It is a thyroid disruptor. [7] [ non-primary source needed ]
Human health effects from acetochlor at low environmental doses or at biomonitored levels from low environmental exposures are unknown. [8] A case of poisoning with extremely swollen genitals as a symptom was reported after contact. [9]
In the United States, acetochlor is the third most frequently detected herbicide in natural waters. [10]
Acetochlor can accelerate metamorphosis in amphibians. [11] It can also affect the development of fish. [11]
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.
Herbicides, also commonly known as weed killers, are substances used to control undesired plants, also known as weeds. Selective herbicides control specific weed species while leaving the desired crop relatively unharmed, while non-selective herbicides kill plants indiscriminately. The combined effects of herbicides, nitrogen fertilizer, and improved cultivars has increased yields of major crops by 3x to 6x from 1900 to 2000.
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.
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.
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.
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 die by 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.
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.
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.
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.
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.
Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one hydrogen atom by an atom of iodine. It is naturally emitted by rice plantations in small amounts. It is also produced in vast quantities estimated to be greater than 214,000 tons annually by algae and kelp in the world's temperate oceans, and in lesser amounts on land by terrestrial fungi and bacteria. It is used in organic synthesis as a source of methyl groups.
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.
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.
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.
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.
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.
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.
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.
Cyanazine is a herbicide that belongs to the group of triazines. Cyanazine inhibits photosynthesis and is therefore used as a herbicide.