A sulfonylurea herbicide for the control of a range of broadleaved and sedge weeds in paddy fields and other crops. It is highly soluble in water, semi-volatile and, based on its physico-chemical properties, appears to have potential for leaching to groundwater. It is not expected to be persistent in the field but can be persistent in water systems. It has a low mammalian toxicity but has high potential for bioaccumulation. No adverse health effects have been identified. Azimsulfuron is moderately toxic to algae, honeybees and earthworms but less so to birds and fish.
Azimsulfuron may be used as an analytical reference standard for the determination of the pesticide in:
- Paddy field water by direct injection using liquid chromatography-hybrid triple quadrupole-linear ion trap-mass spectrometry (LC-QqLIT-MS).
- Tap and leaching water samples by solid-phase extraction (SPE), followed by LC coupled to tandem mass spectrometry (LC-MS/MS).
The production of azimsulfuron involves a multi-step synthesis beginning with the formation of a key sulfonyl chloride intermediate. This is achieved by treating a precursor compound with reagents such as aqueous acetic acid or formic acid and chlorine gas or sodium hypochlorite, in the presence of hydrochloric acid and chlorinated solvents like dichloromethane or tetrahydrofuran. The resulting sulfonyl chloride is then converted into a sulfonamide, which is subsequently reacted with phenyl (4,6-dimethoxypyrimidin-2-yl) carbamate to yield azimsulfuron.
ChEBI: Azimsulfuron is an N-sulfonylurea that is urea in which a nitrogen attached to one of the nitrogens has been replaced by a 4,6-dipyrimidin-2-yl group while a hydrogen attached to the other urea nitrogen has been replaced by a [1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazol-5-yl]sulfonyl group. An acetolactate synthase inhibitor, it is used as a herbicide for the control of a variety of broad-leaved and sedge weeds in paddy fields and other aquatic situations. It has a role as a herbicide and an EC 2.2.1.6 (acetolactate synthase) inhibitor. It is an aromatic ether, a biaryl, a N-sulfonylurea, a member of tetrazoles and a pyrazole pesticide.
Azimsulfuron is a sulfonylurea based pesticide.
Azimsulfuron (DPX‐A8947) is a new rice herbicide introduced in 1996 by DuPont for the control of broadleaf weeds (including hard‐to‐control perennials). At application rates of 8–20 g a.i. ha−1, it provides superior weed control, including E. crus-galli, when compared with the first‐generation sulfonylurea bensulfuron at 50–75 g a.i. ha−1. Azimsulfuron is targeted to replace or supplement bensulfuron in some applications. In Japan, in planted rice, azimsulfuron is used as a premixture with bensulfuron (6 + 30 g a.i. ha−1) to boost the activity against perennial weeds. Good control has also been reported of other members of the Echinochloa family, such as E. hispidula, E. oryzicola, and E. oryzoides. Other weeds controlled include Alisma lanceolatum, A. plantago‐aquatica, Butomus umbellatus, Cyperus difformis, Scirpus maritimus, S. mucronatus, S. supinus, Heteranthera limosa, Potamogeton nodosus, Ammannia coccinea, A. robusta, Bergia capensis, and Lindernia dubia.
Azimsulfuron is sold under the trade names “Gulliver” and “Azin.”
Selective, absorbed by foliage. It inhibits plant amino acid synthesis - acetohydroxyacid synthase (AHAS)
Very unstable, explosivecompound. Very sensitive to heat. Samples have explodedduring analytical combustion. When heated todecomposition it emits toxic fumes of NOx. See AZIDES.
Low toxicity by ingestion,inhalation, skin contact, and intraperitoneal routes. A mildeye irritant. When heated to decomposition it emits toxicvapors of NOx and SOx.
