Bensulide

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Bensulide
Bensulide.svg
Bensulide-from-xtal-3D-bs-17.png
Names
Preferred IUPAC name
S-[2-(Benzenesulfonamido)ethyl] O,O-di(propan-2-yl) phosphorodithioate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.919 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C14H24NO4PS3/c1-12(2)18-20(21,19-13(3)4)22-11-10-15-23(16,17)14-8-6-5-7-9-14/h5-9,12-13,15H,10-11H2,1-4H3 Yes check.svgY
    Key: RRNIZKPFKNDSRS-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C14H24NO4PS3/c1-12(2)18-20(21,19-13(3)4)22-11-10-15-23(16,17)14-8-6-5-7-9-14/h5-9,12-13,15H,10-11H2,1-4H3
    Key: RRNIZKPFKNDSRS-UHFFFAOYAE
  • CC(C)OP(=S)(OC(C)C)SCCNS(=O)(=O)C1=CC=CC=C1
Properties
C14H24NO4PS3
Molar mass 397.50 g·mol−1
AppearanceColorless liquid or white crystalline solid
Density 1.224 g/mL
Melting point 34.4 °C (93.9 °F; 307.5 K)
5.6 mg/L @ 20 C
Solubility in organic solventsSoluble[ vague ]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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 (up to 22.6 kg/ha) when it is used. The EPA classifies bensulide as a general use pesticide. [1]

Contents

Application

Bensulide generally is applied to bare soil, before crops are planted. It is incorporated 1 to 2 inches deep in order for the control of grasses and broadleaf weeds in agricultural crops, residential grass lawns, and golf courses. [2]

Uses

Proturk Goosegrass and Crabgrass Control and Anderson's Goose and Crabgrass Control both have bensulide as one of their active ingredients, along with oxadiazon at a concentration of 5.25% and 1.31% respectively. [3] Bensulide products may be used outdoors by homeowners on lawns and ornamentals, and by professional lawn care operators. Bensulide may be used on turf (primarily golf course greens and tees), on ornamentals, and for greenhouse and outdoor uses in commercial nurseries. 550,000 pounds of active ingredient are used per year, a relatively low value. [1]

Risks

There are a few minor risks that are involved with herbicides that include bensulide. Generally, indirect exposure to it is non-lethal. Dietary exposures from eating food crops treated with bensulide are below the level of concern for the entire U.S. population, including infants and children. Drinking water is not a significant source of exposure. [1]

Risks are of concern for homeowners who apply bensulide, and for children entering turf areas treated with bensulide if label directions are not followed properly. EPA also has risk concerns for workers who mix, load, and/or apply bensulide to agricultural sites, golf courses, and home lawns. Chronic risks are of concern for birds and mammals; risks are posed to some aquatic species. [1]

Related Research Articles

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

Pesticides are substances that are meant to control pests. This includes herbicide, insecticide, nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, microbicide, fungicide, and lampricide. The most common of these are herbicides which account for approximately 80% of all pesticide use. Most pesticides are intended to serve as plant protection products, which in general, protect plants from weeds, fungi, or insects. As an example, the fungus Alternaria solani is used to combat the aquatic weed Salvinia.

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

Herbicides, also commonly known as weedkillers, 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 can be used to clear waste ground, industrial and construction sites, railways and railway embankments as they kill all plant material with which they come into contact. Apart from selective/non-selective, other important distinctions include persistence, means of uptake, and mechanism of action. Historically, products such as common salt and other metal salts were used as herbicides, however these have gradually fallen out of favor and in some countries a number of these are banned due to their persistence in soil, and toxicity and groundwater contamination concerns. Herbicides have also been used in warfare and conflict.

Triclopyr Chemical compound used as a herbicide

Triclopyr is an organic compound in the pyridine group that is used as a systemic foliar herbicide and fungicide.

<span class="mw-page-title-main">Organophosphate</span> Class of organophosphorus compounds

Organophosphates are a class of organophosphorus compounds with the general structure O=P(OR)3, a central phosphate molecule with alkyl or aromatic substituents. They can be considered as esters of phosphoric acid. Like most functional groups organophosphates occur in a diverse range of forms, with important examples including key biomolecules such as DNA, RNA and ATP, as well as many insecticides, herbicides, nerve agents and flame retardants. OPEs have been widely used in various products as flame retardants, plasticizers, and performance additives to engine oil. The popularity of OPEs as flame retardants came as a substitution for the highly regulated brominated flame retardants. The low cost of production and compatibility to diverse polymers made OPEs to be widely used in industry including textile, furniture, electronics as plasticizers and flame retardants. These compounds are added to the final product physically rather than by chemical bond. Due to this, OPEs leak into the environment more readily through volatilization, leaching, and abrasion. OPEs have been detected in diverse environmental compartments such as air, dust, water, sediment, soil and biota samples at higher frequency and concentration.

Alachlor 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.

Vinclozolin 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.

Acetochlor Chemical compound

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.

Pendimethalin Chemical compound

Pendimethalin is an herbicide of the dinitroaniline class used in premergence and postemergence applications to control annual grasses and certain broadleaf weeds. It inhibits cell division and cell elongation. Pendimethalin is listed in the 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, nuts as well as lawns and ornamental plants.

<i>Eleusine indica</i> Species of plant (grass)

Eleusine indica, the Indian goosegrass, yard-grass, goosegrass, wiregrass, or crowfootgrass, is a species of grass in the family Poaceae. It is a small annual grass distributed throughout the warmer areas of the world to about 50 degrees latitude. It is an invasive species in some areas.

Dicamba Chemical compound used as herbicide

Dicamba is a broad-spectrum 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.

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

Acephate is an organophosphate foliar and soil insecticide of moderate persistence with residual systemic activity of about 10–15 days at the recommended use rate. It is used primarily for control of aphids, including resistant species, in vegetables and in horticulture. It also controls leaf miners, caterpillars, sawflies, thrips, and spider mites in the previously stated crops as well as turf, and forestry. By direct application to mounds, it is effective in destroying imported fire ants.

Sulfentrazone Chemical compound

Sulfentrazone is the ISO common name for an organic compound used as a broad-spectrum herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase. It was first marketed in the US in 1997 by FMC Corporation with the brand name Authority.

Dithiopyr Chemical compound

Dithiopyr is a preemergent herbicide for crabgrass control in turf and ornamental grasses. It is effective on 45 grassy and broadleaf weeds. Dithiopyr inhibits root growth of susceptible weeds as well as turf grass and thus should be used only on established turf with a well-developed root system. Its duration of efficacy is approximately 4 months, so lawns should not be reseeded during this time frame following application of the chemical. Dithiopyr acts primarily as a preemergent herbicide but can also be used in early postemergent control of crabgrass.

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">Etofenprox</span> Chemical compound

Etofenprox is a pyrethroid derivative which is used as an insecticide. Mitsui Chemicals Agro Inc. is the main manufacturer of the chemical. It is also used as an ingredient in flea medication for cats and dogs.

Mesotrione Chemical compound used as an herbicide

Mesotrione is the ISO common name for an organic compound that is used as a selective herbicide, especially in maize. A synthetic inspired by the natural substance leptospermone, 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.

2,4-Dichlorophenoxyacetic acid Herbicide

2,4-Dichlorophenoxyacetic acid is an organic compound with the chemical formula C8H6Cl2O3 which is usually referred to by its ISO common name 2,4-D. It is a systemic herbicide which kills most broadleaf weeds by causing uncontrolled growth in them but most grasses such as cereals, lawn turf, and grassland are relatively unaffected.

Aminocyclopyrachlor Chemical compound

Aminocyclopyrachlor is a selective, low-toxicity herbicide that provides pre- and post-emergent control of broadleaf weeds, woody species, vines and grasses on several non-food use sites, such as rights of way, wildlife management areas, recreational areas, turf/lawns, golf courses and sod farms. It was conditionally registered as Imprelis by DuPont in August 2010, and first used in Fall 2010. The chemical is a systemic herbicide and acts by disrupting gene expression. This causes undifferentiated cell division and elongation.

Quinclorac Herbicide, synthetix auxin

Quinclorac is a selective herbicide used primarily to control weeds in rice crops, but is also used on other agricultural crops and is found in some household herbicides for lawn use. Most lawn maintenance companies use the product for the control of annual grass weeds like crabgrass.

Indaziflam Preemergent herbicide discovered in 2009

Indaziflam is a preemergent herbicide especially for grass control in tree and bush crops.

References

  1. 1 2 3 4 Bensulide Facts. Environmental Protection Agency. June 2000.
  2. Antonious GF (2009). "Mobility and half-life of bensulide in agricultural soil". Journal of Environmental Science and Health, Part B. 45: 1. doi:10.1080/03601230903404283.
  3. EPA Office of Pesticide Programs. (October 18, 2007). Risks of bensulide use to Federally Listed California red legged frog (Rana aurora draytonii) (PDF) (Report). Washington, D.C.: Office of Pesticide Programs.