Names | |
---|---|
Preferred IUPAC name rac-N-[-butan-2-yl]-4-tert-butyl-2,6-dinitroaniline | |
Other names
| |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.046.902 |
EC Number |
|
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C14H21N3O4 | |
Molar mass | 295.339 g·mol−1 |
Appearance | Yellow/orange powder [1] |
Density | 1.063 [2] |
Melting point | 59 [2] °C (138 °F; 332 K) |
Vapor pressure | 0.000013 mmHg |
Hazards | |
GHS labelling: [1] [3] | |
Warning | |
H302, H319, H341, H361, H410 | |
P203, P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P318, P330, P337+P317, P391, P405, P501 | |
Flash point | 36 °C (97 °F; 309 K) |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | |
LC50 (median concentration) |
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Butralin is a preemergent herbicide used to control suckers on tobacco in the United States, [4] [5] Australia, [6] Mozambique and, for food crops also, China. [7] It is a dinitroaniline, first registered in the US in 1976. [8] It was used in the EU until a ban in 2009 due to its exotoxicity. [7] [9]
Butralin works by the HRAC mode of action Group D / K1 / 3, (Australian, Global, Numeric respectively), which involves inhibition of microtubule formation, by binding to tubulin, halting growth, and causing depolymerization.
In ryegrass meristems, butralin-treated roots show reduced elongation, but greater diameter. The cells' rate of mitosis lowers 36% after one hour, and they develop multiple nuclei. Butralin's effect is more similar to carbamate herbicides such as chlorpropham rather than other dinitroanilines. [10]
Butralin is sold in Mozambique as "Tobralin 36% EC", made in South Africa. Users are instructed to pour 10 mL on each tobacco plant by hand, and not to unclog nozzles with their mouths. [11] [12]
In China, over 100 tons per year are used, as of 2022, on garlic, soybean, tomato, rice, peanut, pepper, cotton, eggplant, and watermelon. The maximum residue limit is 0.02 to 0.1 mg/kg. [7] The growing Chinese market sells it in 36% or 48% emulsifiable concentrates, and in development as of 2012, a 41% wettable powder. The powder claims to be environmentally friendly, as it lacks the volatile organic molecules such as toluene and xylene used as solvent in EC formulations. [13] The powder is recommended to be applied at 2100 g/Ha (active ingredient). [14]
Butralin is of low acute toxicity. [6] There is no association with lung cancer. [9]
Butralin is likely to be moderately persistent to persistent and relatively immobile in terrestrial environments. Butralin is stable to abiotic hydrolysis and photodegradation on soil. Its characteristics are unlike those of chemicals that leach to groundwater. [8] Butralin's major soil metabolite is 4-tert-butyl-2,6-dinitroaniline. [15] Other major metabolites see the loss of more or all of the carbons and hydrogen over the nitrogen, or loss of oxygen from the nitro groups. The principle residue in crops, however, is the parent butralin. [16]
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). Glyphosate-based herbicides are 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.
Pesticides vary in their effects on bees. Contact pesticides are usually sprayed on plants and can kill bees when they crawl over sprayed surfaces of plants or other areas around it. Systemic pesticides, on the other hand, are usually incorporated into the soil or onto seeds and move up into the stem, leaves, nectar, and pollen of plants.
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.
Diphenylamine is an organic compound with the formula (C6H5)2NH. The compound is a derivative of aniline, consisting of an amine bound to two phenyl groups. The compound is a colorless solid, but commercial samples are often yellow due to oxidized impurities. Diphenylamine dissolves well in many common organic solvents, and is moderately soluble in water. It is used mainly for its antioxidant properties. Diphenylamine is widely used as an industrial antioxidant, dye mordant and reagent and is also employed in agriculture as a fungicide and antihelmintic.
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.
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."
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.
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.
Thiamethoxam is the ISO common name for a mixture of cis-trans isomers used as a systemic insecticide of the neonicotinoid class. It has a broad spectrum of activity against many types of insects and can be used as a seed dressing.
Chlorpropham or CIPC is a plant growth regulator and herbicide used as a sprout suppressant for grass weeds, alfalfa, lima and snap beans, blueberries, cane fruit, carrots, cranberries, ladino clover, garlic, seed grass, onions, spinach, sugar beets, tomatoes, safflower, soybeans, gladioli and woody nursery stock. It is also used to inhibit potato sprouting and for sucker control in tobacco. Chlorpropham is available in emulsifiable concentrate and liquid formulations.
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.
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.
A pesticide, also called Plant Protection Product (PPP), which is a term used in regulatory documents, consists of several different components. The active ingredient in a pesticide is called “active substance” and these active substances either consist of chemicals or micro-organisms. The aims of these active substances are to specifically take action against organisms that are harmful to plants. In other words, active substances are the active components against pests and plant diseases.
Glyphosate-based herbicides are herbicides made of a glyphosate salt usually combined with other ingredients needed to stabilize the formula and allow penetration into plants. Roundup was the first glyphosate-based herbicide, 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.
Prosulfocarb is a pre-emergent herbicide used agriculturally in Australia, the EU, Japan, New Zealand,, Morocco and Iran, for control of annual ryegrass and toad rush in wheat and barley crops. It was introduced to the EU in 1988 and is rapidly growing in use, with sales increasing by over 500% in France since 2008.
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.
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.
Chlornidine is a preemergent herbicide. It is a dinitroaniline used in China and India on soybeans, corn, cotton, sorghum, and peanuts.
Dinitramine is a preëmergent dinitroaniline herbicide incorporated into soil to control weeds for months after. It is no longer approved in the U.S.A., and is not in the European Union, though in Iran it has been used to control annual grasses and broadleaf weeds in cotton and soybeans, as it was in the U.S. as of 1975, where it was also used on sunflower.