Butamifos

Last updated
Butamifos
Butamifos Structural Formula.svg
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.126.299 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 609-231-7
KEGG
PubChem CID
UNII
  • InChI=1S/C13H21N2O4PS/c1-5-11(4)14-20(21,18-6-2)19-13-9-10(3)7-8-12(13)15(16)17/h7-9,11H,5-6H2,1-4H3,(H,14,21)
    Key: OEYOMNZEMCPTKN-UHFFFAOYSA-N
  • CCC(C)NP(=S)(OCC)OC1=C(C=CC(=C1)C)[N+](=O)[O-]
Properties
C13H21N2O4PS
Molar mass 332.35 g·mol−1
Hazards
GHS labelling: [1]
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Warning
H302, H410
P264, P270, P273, P301+P317, P330, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Butamifos is an herbicide that is used to control weeds. [2]

Contents

Production

The production of butamifos is based on N-[chloro(ethoxy)phosphinothioyl]butan-2-amine and 5-methyl-2-nitrophenol and is described in the following reaction sequence: [3]

Synthesis of butamifos Butamifos Synthesis.svg
Synthesis of butamifos

Properties

Butamifos is a chiral molecule. The technical product uses a mixture of the (R)- and (S)-isomers. [4]

In a study, the level of pesticide contamination in soil and water of an agriculturally intensive area in Nepal was investigated. Endosulfan, Iprobefos, monocrotophos, mevinphos, and butamifos were detected in water samples, while cypermethrin, dichlorvos, and cyfluthrin were detected in soil samples. The increased concentration of butamifos in water may be due to higher water solubility and lower affinity for adsorption in soil. [5]

Use

Application and mode of action

Butamifos is used on beans, turf and various vegetables. [3] The active ingredient is a non-systemic, selective herbicide. Its effect is based on inhibition of microtubule formation. It also acts as an acetylcholinesterase inhibitor, making it moderately toxic to mammals. [4] [6]

Trade name

A crop protection product containing the active ingredient butamifos is marketed under the trade name Cremart. [3]

Registration

No plant protection products containing butamifos are registered in the European Union or Switzerland. [7]

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.

<span class="mw-page-title-main">Herbicide</span> Type of chemical used to kill unwanted plants

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 (sometimes called total weed killers kill plants indiscriminately. Due to herbicide resistance – a major concern in agriculture – a number of products combine herbicides with different means of action. Integrated pest management may use herbicides alongside other pest control methods.

Roundup is a brand name of herbicide originally produced by Monsanto, which Bayer acquired in 2018. Prior to the late-2010s formulations, were systemic, 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, which includes genetically modified seeds, represented about half of Monsanto's yearly revenue. 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">Organic movement</span>

The organic movement broadly refers to the organizations and individuals involved worldwide in the promotion of organic food and other organic products. It started during the first half of the 20th century, when modern large-scale agricultural practices began to appear.

<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">Diquat</span> Chemical compound

Diquat is the ISO common name for an organic dication that, as a salt with counterions such as bromide or chloride is used as a contact herbicide that produces desiccation and defoliation. Diquat is no longer approved for use in the European Union, although its registration in many other countries including the USA is still valid.

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

Picloram is a systemic herbicide used for general woody plant control. It also controls a wide range of broad-leaved weeds, but most grasses are resistant. A chlorinated derivative of picolinic acid, picloram is in the pyridine family of herbicides.

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">Pesticide application</span> Delivery of pesticides

Pesticide application refers to the practical way in which pesticides are delivered to their biological targets. Public concern about the use of pesticides has highlighted the need to make this process as efficient as possible, in order to minimise their release into the environment and human exposure. The practice of pest management by the rational application of pesticides is supremely multi-disciplinary, combining many aspects of biology and chemistry with: agronomy, engineering, meteorology, socio-economics and public health, together with newer disciplines such as biotechnology and information science.

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

Pesticide drift refers to the unintentional diffusion of pesticides and the potential negative effects of pesticide application, including off-target contamination due to spray drift as well as runoff from plants or soil. This can lead to damage in human health, environmental contamination, and property damage. Some pesticides are more likely to drift than others which can mean it is more harmful in some cases. For example, fumigants which are gaseous pesticides move easily through air and will drift if not contained. Some pesticides look like a cloud when they drift while others can be invisible and odorless.

<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">Organic food</span> Food complying with organic farming standards

Organic food, ecological food, or biological food are foods and drinks produced by methods complying with the standards of organic farming. Standards vary worldwide, but organic farming features practices that cycle resources, promote ecological balance, and conserve biodiversity. Organizations regulating organic products may restrict the use of certain pesticides and fertilizers in the farming methods used to produce such products. Organic foods are typically not processed using irradiation, industrial solvents, or synthetic food additives.

<span class="mw-page-title-main">Pesticides in the United States</span> Review of the topic

Pesticides in the United States are used predominantly by the agricultural sector, but approximately a quarter of them are used in houses, yards, parks, golf courses, and swimming pools.

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

Methiocarb is a carbamate pesticide which is used as an insecticide, bird repellent, acaricide and molluscicide since the 1960s. Methiocarb has contact and stomach action on mites and neurotoxic effects on molluscs. Seeds treated with methiocarb also affect birds. Other names for methiocarb are mesurol and mercaptodimethur.

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

Bensulide is a selective organophosphate herbicide. It is one of a few organophosphate compounds that are used as an herbicide. Most of the others are used as insecticides. It is used on vegetable crops such as carrots, cucumbers, peppers, and melons and in cotton and turfgrass to control annual grasses such as bluegrass and crabgrass and broadleaf weeds. It is often applied before the weed seeds germinate (pre-emergence) in order to prevent them from germinating. It is available as granules or an emulsifiable concentrate. Estimates place the total use of bensulide in the United States at about 632,000 pounds annually. Application rates may be relatively heavy when it is used. The EPA classifies bensulide as a general use pesticide.

<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.

Pesticide degradation is the process by which a pesticide is transformed into a benign substance that is environmentally compatible with the site to which it was applied. Globally, an estimated 1 to 2.5 million tons of active pesticide ingredients are used each year, mainly in agriculture. Forty percent are herbicides, followed by insecticides and fungicides. Since their initial development in the 1940s, multiple chemical pesticides with different uses and modes of action have been employed. Pesticides are applied over large areas in agriculture and urban settings. Pesticide use, therefore, represents an important source of diffuse chemical environmental inputs.

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. "Butamifos". pubchem.ncbi.nlm.nih.gov. Retrieved 5 August 2022.
  2. Toshiyuki Katagi (March 1993), "Photochemistry of organophosphorus herbicide butamifos", Journal of Agricultural and Food Chemistry (in German), vol. 41, no. 3, pp. 496–501, doi:10.1021/jf00027a028, ISSN   0021-8561
  3. 1 2 3 Thomas A. Unger (1996), [ , p. 376, at Google Books "Butamifos"], Pesticide Synthesis Handbook (in German), Elsevier, p. 376, doi:10.1016/b978-081551401-5.50299-9, ISBN   978-0-8155-1401-5 {{citation}}: Check |url= value (help)
  4. 1 2 Butamifos in the Pesticide Properties DataBase (PPDB)
  5. Kafle, B. K., Pokhrel, B., Shrestha, S., Raut, R., Dahal, B. M. (2015), "Determination of pesticide residues in water and soil samples from Ansikhola watershed, Kavre, Nepal", International Journal of Geology, Earth & Environmental Sciences (in German), vol. 5, no. 2, pp. 119-127{{citation}}: CS1 maint: multiple names: authors list (link)
  6. Paranjape, Kalyani. (2014), [ , p. 74, at Google Books The pesticide encyclopedia] (in German), Wallingford, Oxfordshire UK: CABI, p. 74, ISBN   978-1-78064-014-3 {{citation}}: Check |url= value (help)
  7. "European Commission Directorate-General for Health and Food Safety".