Triazolopyrimidine sulfonamides

The triazolopyrimidine-2-sulfonamides 45 were prepared from the 1,2,4-triazole 40 by reaction with phenyl chloroformate to give 41, whose chlorination gave 42, then transformed to the amide 43. Hydrolysis of... 

Sulfonylureas, imidazolinones, triazolopyrimidine sulfonamides Acetolactate synthase 73... 

Penoxsulam has a toxicological profile similar to other triazolopyrimidine sulfonamides. There was no indication of acute or chronic toxicity issues to mammalian and non-target organisms such as fish, fresh water invertebrates, honey bees, earthworm and beneficial arthropods. 

However, these compounds are weaker herbicides than the triazolopyrimidine sulfonamides. 

Gerwick BC, Deboer GJ, Schmitzer PR, Mechanism of Tolerance to Triazolopyrimidine Sulfonamide. In Herbicides Inhibiting Branch Chain Amino Acid Biosynthesis, Stetter, J. Ed., Spinger-Verlag, Germany, 1994, Vol. 10, pp 145-160. 

Flumetsulam is one of several in the triazolopyrimidine sulfonamide class of herbicide. This class of AHAS inhibitors is effective for broadleaf weed... 

This pathway exists in plants and microorganisms such as bacteria, fungi and algae. ALS is the primary target site of action for at least four structurally distinct classes of herbicides including the sulfonylureas (SU), the imidazolinones (IM), the triazolopyrimidine sulfonamides (TP) and oin pyrimidinyl carboxy herbicides (PC)(Fig. 2). 

Three distinct classes of herbicidally active chemicals inhibit ALS sulfonylureas, imidazolinones, and triazolopyrimidine sulfonamides. " Recently, a fourth type, pyrimidinyl oxobenzoic acids, has been patented. ... 

Triazolopyrimidine, Triazolo[l, 5-a]pyrimidine, Triazolo[l, 5-c]pyrimidine. Sulfonamide, Penoxsulam... 

The structure-activity trends for the triazolo[15-a]pyrazines have not been studied as extensively as other members of triazolopyrimidine sulfonanilides [51]. Table 2.4.10 shows the activity on broadleaf and grass species for a series of substitutions on the fused heterocyclic portion of 34. The highest levels of activity on grass and broadleaf species are observed when both 5- and 8-positions are substituted with methoxy (34, R = R = OMe). However, the herbicidal activity observed for 34 is weaker than that for the triazolo[l,5-a]pyrimidine sulfonamides. 

The activity of the non-halogenated sulfonamide herbicide asulam (105 1965, Asulox , May Baker 1-10 kg-a.i. ha ) [196] was remarkable improved by replacing the 4-aminophenyl ring with a halogenated triazolopyrimidine moiety and/or by replacement the N-methoxycarbonyl group with a series of ortho-halogenated electron-deficient phenyl rings such as 2,6-difluoro-, 2,6-dichloro- or... 

Soil column extraction (SCE) SCE consists on a specific solvent percolation to a column packed with the sampled material (soil, sediment) containing herbicides. About 100mmoll potassium phosphate buffer adjusted to pH 8 at ambient temperature readily extracts imidazolinones, diphenyl ethers, sulfonyl ureas, aryloxyphenoxypropionic acids, and triazolopyrimidines from soil samples. The same SCE procedure was applied to 0.2-0.4% carbon-containing sediments for isolation of sulfonamides and triazines with recoveries ranging from 63% to 99%. Further cleanup (e.g., on Carbograph cartridges) or concentration (SPME) may sometimes be necessary. 

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