Sulfonamide herbicides

Fontaine, D.D., R.G. Lehmann, and J.R. Miller. 1991. Soil adsorption of neutral and anionic forms of a sulfonamide herbicide, flumetsulam. J. Environ. Qual. 20(4) 759-762. 

M. Rodriguez and D.B. Orescan, Confirmation and quantitation of selected sulfonylurea, imida-zolinone, and sulfonamide herbicides in surface water using electrospray LC/MS, Anal. Chem., 70, 2710-2717 (1998). 

SIM with three compound specific ions can be applied, as for instance demonstrated by Wang and Budde [101] for sixteen carbamate, urea and thioiuea pesticides and herbicides, by Rodriguez and Orescan [51] for selected sulfonylurea, imidazolinone, and sulfonamide herbicides, and by Yu et al. [17] for 52 carbamates, thiocaibamates, and phenylureas. In the latter case, computer-controlled optimization of the MS measurement conditions is performed. The most prominent ion, either a protonated or an ammoniated molecule, is used for quantitation. The dwell time for each ion in SIM was 0.02 s with an inter-charmel delay of 0.02 s, i.e., 2 s are needed for each data point in the chromatogram. Detection limits ranged from 0.09 to 19 pg/1 with 50-pl injections. 

Triazole-sulfonamide herbicides are egosterol biosynthesis inhibitors, and include prop-iconazole (100) and flusilazole (101). Apart from a range of sulfonamides introduced in 1992, no further important developments occurred until the introduction of protox-inhibiting herbicides, mainly diphenyl ethers and cyclic imides, the latter including aryl... 

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... 

A single multiresidue method was developed to determine 109 priority compoimds listed in the 76/464/EEC Coimcil Directive on Pollution of the EU [49]. For trapping analytes, automated off-line SPE with a polymeric sorbent "Oasis" 60 mg cartridge, was optimized. A multianalyte method for the confirmation and quantitation of 16 selected sulfonylurea, imidazolinone, and sulfonamide herbicides in surface water has been proposed [50]. This method is based on analyte extraction with a polymeric material (RP-102) and extract cleanup with a strong anion exchanger (SAX) cartridge stacked on... 

Furlong, E.T. et al.. Routine determination of sulfonylurea, imidazolinone, and sulfonamide herbicides at nanogram-per-Uter concentrations by solid-phase extraction and liquid chromatography/mass spectrometry, Sci. Total Environ., 248,135, 2000. 

Plan of Study to Determine the Occurrence of Sulfonylurea, Sulfonamide, and Imidazolinone Herbicides in Surface and Ground-Water of the Midwestern United States. US Geological Survey, Washington, DC (1998). Also available on the World Wide Web http //webserver.cr.usgs.gov/midconherh/html/workplan98.html, accessed September 2002. 

The types of compounds that are of concern as contaminants are chlorinated insecticides, organophosphates, herbicides, fungicides, fas-ciolicides (phenolic compounds administered to cattle to control liver flukes), antibiotics and sulfonamides, detergents and disinfectants, and polychlorinated biphenyls (PCBs). Contaminants in milk have been reviewed by Kroger (1974) and Snelson (1979). In several cases, allowable levels for specific contaminants in milk have been set by the World Health Organization. Surveys have seldom revealed levels in excess of such standards. 

Compounds 272 are useful as herbicides and inhibitors of nitrification of amino nitrogen in soil, and they are used for the control of Echinochioa crusgalli without damage to rice. 5-Fluoromethyl-7-methoxy-l,2,4-triazolo-[l,5-a]pyrimidine-2-sulfonamides are useful for the control of pigweed (85USP4818273). 

Chemical Name 4-(dipropylamino)-3,5-dinitrobenzene-sulfonamide 3,5-dinitro-lV, A -dipropylsulfanilamide Uses herbicide for pre-emergence control of many annual grasses and broadleaf weeds in cotton, fruit trees, vines, nut trees, soybeans, groundnuts, oilseed rape, sunflowers, lucerne, peas, sweet potatoes, mint, ornamentals and also used in noncrop areas. 

Thiophene sulfonamide DoM chemistry is by far the most highly explored in view of the agrochemical significance of the sulfonylurea herbicides [23]. Potential for regioselective deprotonation as a function of kinetic or thermodynamic control 38 may lead to 3- or 5-... 

Uses herbicide, soyabeans, maize Trade names Broadstrike, (DowElanco) Type pyrimidine, triazole, sulfonamide... 

A wide variety of sulfamate esters have been synthesised and screened as herbicides, pharmaceutical agents and sweeteners (see Chapter 11, p. 240). Sulfamates containing a primary amino group (124) are conveniently prepared by condensation of the appropriate alcohol with sulfamoyl chloride (125) in DMF in the presence of sodium hydride (Scheme 50). An illustrative example is provided by the conversion of substituted p-phenylethanols (126) to the corresponding sulfamates (127) (Scheme 50). Compounds of type (127) exhibit anticonvulsant and carbonic anhydrase activity and may be useful in the treatment of epilepsy and glaucoma. Sulfamoyl chlorides (125) may be prepared by treatment of amines or amine hydrochlorides with sulfuryl chloride (128). An analogous reaction also occurs with dialkyl sulfonamides (129) (Scheme 51). 

A wide variety of organosulfur compounds show useful biological activity examples include the sulfonamide antibacterials and diuretics, penicillin and cephalosporin antibiotics, the antiulcer drug ranitidine, and agrochemicals such as the thiophosphoryl (P=S) insecticides like malathion, herbicides like chlorsulfuron, many fungicides like the dithiocarbamates (see Chapter 9, p. 148) and captan (see Chapter 9, p. 151), and sulfone acaricides like tetradifon (see Chapter 7, p. 104). 

A typical thermospray ionization mass spectrum for a sulfonylurea contains a weak protonated molecular ion and three to four characteristic fragment ions. Figure 2 shows the thermospray positive ion mass spectrum for HARMONY. The spectrum contains a protonated molecular ion at m/z 388, the sulfonamide ammonium adduct ion at m/z 239 and the protonated triazine urea fragment ion at m/z 184. At the same time, Figure 3 shows the positive ion thermospray mass spectrum for LONDAX. It contains the protonated pyrimidine amine at m/z 156, the protonated pyrimidine urea is at m/z 199 and the sulfonamide ammonium adduct ion at m/z 247. LONDAX (bensulfuron methyl) is a sulfonylurea rice herbicide and it elutes between EXPRESS and CLASSIC if we use the LC conditions outlined in Figure 1. HARMONY and LONDAX thermospray spectra were generated with the thermospray vaporizer tip temperature at 150°C and the source block temperature at 320°C. 

For the six sulfonylurea herbicides included in Figure 1, we monitored the protonated molecular ion fen each herbicide in addition to one or two major fragment ions. Table 1 shows the ions selected for each of the sulfonylurea and Figure 4 shows the ion traces for each compound. The table shows two ions which are common for some of these sulfonylurea herbicides. HARMONY, ALLY and GLEAN contain the same triazine urea ion at m/z 184 while ALLY, OUST and EXPRESS contain the same sulfonamide ions at m/z 233. Selecting these common ions for quantitation will increase the overall sensitivity for multiresidue analysis. 

Sulfonyl chlorides have extensive uses in organic synthesis in the preparation of sulfonamides and sulfonate esters. Methanesulfonyl chloride is a key raw material in the synthesis of critical components for photographic color developing formulations, as well as for herbicides and pharmaceuticals. 

The reaction of 2-amino-5,7-dimethyl-l,8-naphthyridine 403 with 2-chlorophenyl sulfonylchloride produces sulfonamide 404, which possesses herbicidal and growthcontrolling properties (1990GEP3804990). Condensation of amine 403 with trichloroacetone affords a mixture of angular imidazo[l, 2-a][l, 8]naphthyridines 405-407 (1992JHC691). 

Sulfonamides Pharmaceuticals, herbicides, enzymatic degradation product of corrosion inhibiting agents Water... 

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