Prosulfocarb

Last updated
Prosulfocarb [1] [2]
Prosulfocarb v2.svg
Names
IUPAC name
S-Benzyl N,N-dipropylcarbamothioate
Other names
Prosulfocarb, A8545C
Identifiers
ECHA InfoCard 100.100.363 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
Properties
C14H21NOS
Molar mass 251.39 g·mol−1
AppearanceColourless - pale yellow
Odor Aromatic
Density 1049 kg/m3 [1]
Melting point -20 °C [3]
Boiling point 341 °C [3]
Insoluble [3]
Solubility in xylene Soluble [3]
Solubility in acetone Soluble [3]
Solubility in heptane Soluble [3]
Solubility in ethyl acetate Soluble [3]
Vapor pressure 0.79 mPa [3]
Hazards
GHS labelling:
GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Warning
H227, H302, H317, H335, H371, H373, H401
Flash point 167.1 °C [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Prosulfocarb is a pre-emergent herbicide used agriculturally in Australia, the EU, Japan, New Zealand, (since 2020), Morocco and Iran, for control of annual ryegrass and toad rush in wheat and barley crops. [4] [5] [6] [3] It was introduced to the EU in 1988 and is rapidly growing in use, with sales increasing by over 500% in France since 2008. [7]

Contents

Prosulfocarb is a thiocarbamate, and is absorbed by the roots of germinating seedlings to inhibit growth in the meristem by inhibiting fat synthesis, [4] of resistance HRAC Group J, (Aus), [4] K3/N, (Global), 15. (numeric) [8] Applying prosulfocarb repeatedly builds weed resistance but undoes trifluralin (Group 3) resistance, as they have opposing mechanisms: prosulfocarb is resisted by decreasing pesticide metabolism; trifluralin is resisted by increasing metabolism. [9]

Application

To target annual ryegrass, 2.5L/ha (of 800 g/L emulsifiable concentrate) is prepared and sprayed before sowing. It can be applied to barley post-emergence, but if applied wrongly may cause crop damage. [10] Prosulfocarb does not need much moisture to be applied efficably, due to low volatility. [11]

Prosulfocarb is often applied alongside s-Metolachlor and pyroxasulfone, or in Australia with trifluralin, with which it more efficiently circumvents weed resistance. [12]

Prosulfocarb prevents target weeds from germinating, or failing that, the shoots grow swollen and bright green. [10]

Toxicology

Prosulfocarb's LD50 toxicity is 1820 mg/kg orally for rats, [2] which is comparable to paracetamol. The human toxicological effect is low. [7] Prosulfocarb itself is not a combustible, but formulations can be due to other components. (e.g. solvent naphtha) [13] Prosulfocarb is an irritant. [3]

What limited mammalian toxicity exists, seems to affect the liver and kidneys, and in long-term studies, reduces appetite. Evidence does not show any carcinogenicity or genotoxicity. No toxic effect on the reproduction is shown. Prosulfocarb may have weak teratogenic potential, though there is no convincing evidence for it. [14]

Environmental effect

Prosulfocarb is toxic to aquatic organisms; it is mandatory in Australia not to spray it within 20 metres upwind of aquatic or wetland areas or to apply by air. Nor if heavy rain is expected, to prevent runoff. [4] It is not persistent in soil, with a halflife of 35 days. Prosulfocarb bioaccumulates, and has slight mobility in soil. [13] Prosulfocarb's halflife in water (measured in ditches) is only 2.9 days. [15]

Prosulfocarb was detectable in 97% of beeswax samples in a Swiss study, to a maximum level of 21 μg/kg, and was detectable in 27% of pollen. [16]

Production

Global herbicide production is in TGAC form, typically 95-98% purity, whence it is shipped and locally formulated into commercially practical formulations, a mix with a solvent such as solvent naptha [13] and other agents to make good mixing behaviour. Tech production is often in the USA, Japan, China, and India, the top four global agrochemical producers. [17] Hermani, in Bharuch, India, has the capacity for 5000 tonnes of technical per year; Punjab Chemicals, in Dera Bassi, another 3000; [18] Weifang Sino-Agri, China, another 1000 tonnes per year. [19]

Synthesis

Prosulfocarb is synthesised by combination of dipropyl amine and phosgene, the amine replacing a chlorine atom, and this is then combined with benzyl mercaptan which takes the place of phosgene's other chlorine atom. The other order, adding the mercaptan to phosgene first, is also possible. [20]

Lists

These lists are non-exhaustive.

Prosulfocarb has been used to control the following weeds: annual ryegrass, Lolium rigidum , [4] which is highly resistant to other herbicides, notably glyphosate, barley grass, toad rush, red and white fumitory, paradoxa grass (canary grass), Phalaris spp., sand fescue, silver grass (Vulpia spp.), soil surface wild oats, wireweed (hogweed), suppression of brome grass, deadnettle, rough poppy and yellow burr weed. [21]

Prosulfocarb has been applied to the following crops: wheat and barley. [4]

Prosulfocarb has been sold under these tradenames: Prosulfocarb 800, (4Famers, Genfarm, Reylon), Profuse, Arcade, (Syngenta), Countdown, Boxer Gold, (combination with s-Metolachlor), Defi, and Dian.

Related Research Articles

<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 kill plants indiscriminately. The combined effects of herbicides, nitrogen fertilizer, and improved cultivars has increased yields of major crops by three to six times from 1900 to 2000.

<span class="mw-page-title-main">Weed control</span> Botanical component of pest control for plants

Weed control is a type of pest control, which attempts to stop or reduce growth of weeds, especially noxious weeds, with the aim of reducing their competition with desired flora and fauna including domesticated plants and livestock, and in natural settings preventing non native species competing with native species.

<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.

<i>Lolium</i> Genus of plants (tufted grasses)

Lolium is a genus of tufted grasses in the bluegrass subfamily (Pooideae). It is often called ryegrass, but this term is sometimes used to refer to grasses in other genera.

<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 a toxic 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 worldwide. It is quick-acting and non-selective, killing green plant tissue on contact.

<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">Pendimethalin</span> Chemical compound

Pendimethalin is an herbicide of the dinitroaniline class used premergently and postemergently to control annual grasses and certain broadleaf weeds. It inhibits cell division and cell elongation. Pendimethalin is a K1-group according to the Herbicide Resistance Action Committee (HRAC) classification and is approved in Europe, North America, South America, Africa, Asia and Oceania for different crops including cereals, corn, soybeans, rice, potato, legumes, fruits, vegetables, and nuts, plus lawns and ornamental plants.

<span class="mw-page-title-main">Trifluralin</span> Weed control herbicide

Trifluralin is a common pre-emergent selective herbicide, a dinitroaniline. With about 14 million pounds (6,400 t) used in the United States in 2001, and 3–7 million pounds (1,400–3,200 t) in 2012, it is one of the most widely used herbicides. Trifluralin is also used in Australia, and New Zealand, previously in the EU. Introduced in 1964, Trifluralin was the first organofluorine compound used as an agrochemical.

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

Mesotrione is a selective herbicide used mainly in maize crops. It is a synthetic compound inspired by the natural substance leptospermone found in the bottlebrush tree Callistemon citrinus. It inhibits the enzyme 4-hydroxyphenylpyruvate dioxygenase (HPPD) and is sold under brand names including Callisto and Tenacity. It was first marketed by Syngenta in 2001.

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

Benfluralin is an herbicide of the dinitroaniline class. The mechanism of action of benfluralin involves pre-emergent inhibition of mitosis, root and shoot development, same as trifluralin, from which benfluralin was developed in 1963.

<i>Lolium rigidum</i> Species of grass

Lolium rigidum is a species of annual grass. Common names by which it is known include annual ryegrass, a name also given to Italian ryegrass, rigid ryegrass, stiff darnel, Swiss ryegrass and Wimmera ryegrass. It is a native of southern Europe, northern Africa, the Middle East and the Indian subcontinent and is grown as a forage crop, particularly in Australia, where it is also a serious and economically damaging crop weed.

<span class="mw-page-title-main">Quizalofop</span> Weed control herbicide

Quizalofop is a chlorophenxy and phenoxy herbicide that works by inhibition of acetyl-CoA-carboxylase to selectively control grasses, without affecting broadleaf crops. It may be shortened to QPE, from Quizalofop-P-Ethyl. It is a Group 1 / A / A herbicide, used in Australia, Morocco and Europe.

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

Butafenacil is the ISO common name for an organic compound of the pyrimidinedione chemical class used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase to control broadleaf and some grass weeds in crops including cereals and canola.

<span class="mw-page-title-main">Chlorsulfuron</span> ALS inhibitor herbicide

Chlorsulfuron is an ALS inhibitor herbicide, and is a sulfonylurea compound. It was discovered by George Levitt in February 1976 while working at DuPont, which was the patent assignee.

<span class="mw-page-title-main">Diflufenican</span> Weed control herbicide

Diflufenican is a herbicide used to control weeds including wild radish and wild turnip weeds or suppress capeweed, crassula, marshmallow or shepherd's purse, in clover pasture, lupins, lentils or field peas. It has seen use in Australia, Europe, and in Feb 2024 registered in North America by the PMRA, EPA registration pending, for use on soybean and corn.

<span class="mw-page-title-main">Isoproturon</span> Weed control herbicide

Isoproturon (IPU) is a urea class selective herbicide, which has been used to control annual grasses and many broad leafed weeds in wheat, barley, rye and triticale.

<span class="mw-page-title-main">Nitralin</span> Weed control herbicide

Nitralin is a selective pre-emergent dinitroaniline herbicide that is closely related to trifluralin, and released two years later in 1966. Today it is largely obsolete. It was used in the USA, France and Australia to control annual grasses and broad-leaved weeds, and was applied on vines, crops and turf.

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

Profluralin is a dinitroaniline herbicide used preëmergently to control annual grasses and broadleaf weeds, in cotton, soybeans, peanuts, sunflower, cabbage, cauliflower, tomato and others. Profluralin has largely fallen out of use. It rose out of the related, still in common use, trifluralin.

<span class="mw-page-title-main">Butralin</span> Weed control herbicide

Butralin is a herbicide, used to control suckers on tobacco in the United States,, Australia, Mozambique and, for food crops also, China. It is a preëmergent dinitroaniline, first registered in the US in 1976. It was used in the EU, until a ban for exotoxicity in 2009.

<span class="mw-page-title-main">Ethalfluralin</span> Weed control herbicide

Ethalfluralin is a herbicide. It is a preëmergent dinitroaniline developed from trifluralin, used to control annual grasses and broad-leaved weeds. It was synthesised in 1971, first sold in Turkey in 1975, the United States in 1983. It is used on soybeans, peanuts, potatoes, and as of 2023, is the first conventional herbicide the EPA permits on hemp, as ethalfluralin leaves no residue in the plant. Ethalfluralin is not used domestically.

References

  1. 1 2 3 "Prosulfocarb SDS" (PDF). ChemicalBook. Retrieved 5 August 2024.
  2. 1 2 "Prosulfocarb Standard SDS" (PDF). FujiFilm. Retrieved 5 August 2024.
  3. 1 2 3 4 5 6 7 8 9 10 "Prosulfocarb (Ref: SC 0574)". Pesticide Properties DataBase. Retrieved 8 August 2024.
  4. 1 2 3 4 5 6 "4Farmers Australia Prosulfocarb Leaflet" (PDF). www.4farmers.com.au. 4Farmers Australia. Retrieved 5 August 2024.
  5. ↑ "Prosulfocarb 800 Label" (PDF). GenFarm. Retrieved 5 August 2024.
  6. ↑ "Permission granted for new potato protector". www.epa.govt.nz. 10 August 2020.
  7. 1 2 Devault, Damnien; Guillemin, Jean-Philippe; Maurice, Millet; Eymery, Frank (January 2022). "Prosulfocarb at center stage!". Environmental Science and Pollution Research. doi:10.1007/s11356-019-06928-8 . Retrieved 5 August 2024.
  8. ↑ "2024 HRAC Global Herbicide MOA Classification Master List". Herbicide Resistance Action Committee.
  9. ↑ Busi, Roberto; Goggin, Danica E; Onofri, Andrea; Boutsalis, Peter; Preston, Christopher; Powles, Stephen B; Beckie, Hugh J (December 2020). "Loss of trifluralin metabolic resistance in Lolium rigidum plants exposed to prosulfocarb recurrent selection". Pest Management Science. 76 (12): 3926–3934. doi:10.1002/ps.5993.
  10. 1 2 "4Farmers Prosulfocarb 800 EC Infosheet" (PDF). www.4farmers.com.au. 4Farmers Australia. Retrieved 5 August 2024.
  11. ↑ "Australia - Give your barley growers value through efficacy and flexibility in ARG control". Grainews.
  12. ↑ Kleemann, Samuel G. L.; Preston, Christopher; Gill, Gurjeet S. (2014). "Influence of Seeding System Disturbance on Preplant Incorporated Herbicide Control of Rigid Ryegrass (Lolium rigidum) in Wheat in Southern Australia" (PDF). Weed Technology (28): 323–331. Retrieved 5 August 2024.
  13. 1 2 3 "4Farmers Prosulfocarb Herbicide Safety Data Sheet" (PDF). 4farmers.com.au. 4Farmers Australia. Retrieved 5 August 2024.
  14. ↑ "Conclusion regarding the peer review of the pesticide risk assessment of the active substance prosulfocarb". www.efsa.europa.eu. 28 August 2007. doi: 10.2903/j.efsa.2007.111r .
  15. ↑ Adriaanse, Paulien I; Boesten, Jos JTI; Crum, Steven JH (June 2013). "Estimating degradation rates in outdoor stagnant water by inverse modelling with TOXSWA : a case study with prosulfocarb". Pest Management Science. 69 (6): 755–767. doi:10.1002/ps.3435.
  16. ↑ Kast, Christina; Müller, Jan; Fracheboud, Marion (15 October 2024). "Temporal entry of pesticides through pollen into the bee hive and their fate in beeswax". Environmental Science and Pollution Research. 31 (51): 61060–61072. doi:10.1007/s11356-024-35224-3.
  17. ↑ "22 active ingredient patents to expire by 2030: What it means for Indian agrochemical companies". Grainews.
  18. ↑ "Will India's Herbicide Boom Year Continue?". Grainews.
  19. ↑ "Weifang Sino-Agri Union's 1,000-tons prosulfocarb technical project completed". Grainews.
  20. ↑ Unger, Thomas A. (1996). Pesticide synthesis handbook (1st ed.). Noyes Publications. p. 115.
  21. ↑ "Prosulfocarb 800 Label" (PDF). Reylon.
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