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Mesotrione
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Mesotrione
Mesotrione is a selective herbicide used mainly in maize crops and has also been shown to have weak insecticidal properties. 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.
The invention of the triketone class of herbicides had its beginnings in an observation in 1977 of allelopathic weed control near a bottlebrush tree, Callistemon citrinus. Chemists at the Stauffer Chemical Company identified the compound responsible as leptospermone, a known natural product which had not previously been reported as having biological activity. Extensive work on analogues led to the discovery and development of sulcotrione and mesotrione.[25][26}[12]
The triketone herbicides were found to be effective on a wide range of commercially-important weed species and to have both pre- and post-emergence activity. Mesotrione was chosen for development (by Zeneca Agrochemicals under the code number ZA1296) because it controls a wide range of broad-leaved weeds that compete with maize and can also suppress some annual grass weeds that may be present in the crop. It achieves this selectivity and lack of damage to the crop owing to its greater potency on the target enzyme found in dicotyledons than monocotyledons and because maize can metabolise the compound in the dione-containing ring.
The synthesis of mesotrione was first disclosed in patents filed by ICI, who had acquired Stauffer in 1987. 1,3-Cyclohexanedione is first reacted with the acid chloride of 4-(methylsulfonyl)-2-nitrobenzoic acid under conditions in which the enolic hydroxyl group of the diketone reacts to form the benzoylated derivative. In a separate step, this is rearranged to mesotrione using a catalytic amount of cyanide ion derived from acetone cyanohydrin.
Mesotrione inhibits the enzyme 4-hydroxyphenylpyruvate dioxygenase (HPPD). It is an extremely potent inhibitor of HPPD in laboratory tests using the plant Arabidopsis thaliana, with a Ki value of about 10 pM. In plants, HPPD is necessary for the biosynthesis of tocopherols and of plastoquinone, which is essential to carotenoid production. Inhibiton of the pathway ultimately leads to bleaching of leaves as chlorophyll is degraded, followed by plant death.
Mesotrione is made available to end-users only in formulated products. These use non-powdery material with reduced or no use of hazardous solvents, for example suspension concentrates. The herbicide is compatible with other compounds that may be mixed by the farmer to extend control to the grass weeds which mesotrione itself does not kill.
Mesotrione is a systemic pre- and post-emergence herbicide for the selective contact and residual control of broadleaf weeds in field corn, seed corn, yellow popcorn and sweet corn. Mesotrione possesses a broad spectrum of activity on commercially important broadleaf weeds including Abutilon theophrasti, Amaranthus powellii, Amaranthus retroflexus, Chenopodium album, Datura stramonium, Digitaria sanguinalis, Lamium purpureum, Polygonum persicaria, Rumex crispus, Senecio vulgaris, Solanum nigrum, Stellaria media and Xanthium strumarium. In addition, its properties mean that it can be applied to soil so emerging weeds take it up and are controlled. Alternatively, spraying after weeds are already present in the crop will also lead to control. This combination of properties has meant that mesotrione achieved widespread use very quickly and reached annual sales of more than $400 million by 2011. The product is used at application rates of 75-150 g/ha.
The estimated annual use of mesotrione in US agriculture is mapped by the US Geological Service and shows an increasing trend from its introduction in 2001 to 2018, the latest date for which figures are available and now reaching 4,500,000 pounds (2,000,000 kg). As would be expected for a compound used almost exclusively in maize, the heaviest use is in the Corn Belt.
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Mesotrione
Mesotrione is a selective herbicide used mainly in maize crops and has also been shown to have weak insecticidal properties. 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.
The invention of the triketone class of herbicides had its beginnings in an observation in 1977 of allelopathic weed control near a bottlebrush tree, Callistemon citrinus. Chemists at the Stauffer Chemical Company identified the compound responsible as leptospermone, a known natural product which had not previously been reported as having biological activity. Extensive work on analogues led to the discovery and development of sulcotrione and mesotrione.[25][26}[12]
The triketone herbicides were found to be effective on a wide range of commercially-important weed species and to have both pre- and post-emergence activity. Mesotrione was chosen for development (by Zeneca Agrochemicals under the code number ZA1296) because it controls a wide range of broad-leaved weeds that compete with maize and can also suppress some annual grass weeds that may be present in the crop. It achieves this selectivity and lack of damage to the crop owing to its greater potency on the target enzyme found in dicotyledons than monocotyledons and because maize can metabolise the compound in the dione-containing ring.
The synthesis of mesotrione was first disclosed in patents filed by ICI, who had acquired Stauffer in 1987. 1,3-Cyclohexanedione is first reacted with the acid chloride of 4-(methylsulfonyl)-2-nitrobenzoic acid under conditions in which the enolic hydroxyl group of the diketone reacts to form the benzoylated derivative. In a separate step, this is rearranged to mesotrione using a catalytic amount of cyanide ion derived from acetone cyanohydrin.
Mesotrione inhibits the enzyme 4-hydroxyphenylpyruvate dioxygenase (HPPD). It is an extremely potent inhibitor of HPPD in laboratory tests using the plant Arabidopsis thaliana, with a Ki value of about 10 pM. In plants, HPPD is necessary for the biosynthesis of tocopherols and of plastoquinone, which is essential to carotenoid production. Inhibiton of the pathway ultimately leads to bleaching of leaves as chlorophyll is degraded, followed by plant death.
Mesotrione is made available to end-users only in formulated products. These use non-powdery material with reduced or no use of hazardous solvents, for example suspension concentrates. The herbicide is compatible with other compounds that may be mixed by the farmer to extend control to the grass weeds which mesotrione itself does not kill.
Mesotrione is a systemic pre- and post-emergence herbicide for the selective contact and residual control of broadleaf weeds in field corn, seed corn, yellow popcorn and sweet corn. Mesotrione possesses a broad spectrum of activity on commercially important broadleaf weeds including Abutilon theophrasti, Amaranthus powellii, Amaranthus retroflexus, Chenopodium album, Datura stramonium, Digitaria sanguinalis, Lamium purpureum, Polygonum persicaria, Rumex crispus, Senecio vulgaris, Solanum nigrum, Stellaria media and Xanthium strumarium. In addition, its properties mean that it can be applied to soil so emerging weeds take it up and are controlled. Alternatively, spraying after weeds are already present in the crop will also lead to control. This combination of properties has meant that mesotrione achieved widespread use very quickly and reached annual sales of more than $400 million by 2011. The product is used at application rates of 75-150 g/ha.
The estimated annual use of mesotrione in US agriculture is mapped by the US Geological Service and shows an increasing trend from its introduction in 2001 to 2018, the latest date for which figures are available and now reaching 4,500,000 pounds (2,000,000 kg). As would be expected for a compound used almost exclusively in maize, the heaviest use is in the Corn Belt.
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