Fluoroalkanesulfonanilides, a new class of herbicides

Trepka, Robert D.; Harringon, Joseph K.; Robertson, Jerry E.; Waddington, J.

doi:10.1021/jf60172a040

Cited by 18 publications

(12 citation statements)

References 4 publications

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“…Common alkanesulfonylamides, however, found little application in the pharmaceutical or agrochemical area at that time [1]. When fluorine was introduced into these common alkanesulfonylamides, their biological activity was satisfactorily improved [1][2][3][4]. For example, Trepka and Moore found that fluorinated N-phenylalkanesulfonylamides showed potent herbicidal and anti-inflammatory activities in 1970s [2][3][4].…”

Section: Introductionmentioning

confidence: 99%

“…When fluorine was introduced into these common alkanesulfonylamides, their biological activity was satisfactorily improved [1][2][3][4]. For example, Trepka and Moore found that fluorinated N-phenylalkanesulfonylamides showed potent herbicidal and anti-inflammatory activities in 1970s [2][3][4]. Lu recently reported that N-alkylfluoroalkanesulfonylamides were environment-friendly insecticides [5].…”

Section: Introductionmentioning

confidence: 99%

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Determination of pKa values of fluoroalkanesulfonamides and investigation of their nucleophilicity

Zhang

Wang

Chen

et al. 2010

Journal of Fluorine Chemistry

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Determination of pKa values of fluoroalkanesulfonamides and investigation of their nucleophilicity

Zhang

Wang

Chen

et al. 2010

Journal of Fluorine Chemistry

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“…We also tried to change the acidic group to a sulfonamide group to provide a broader weeding spectrum. 8) As a result, we have succeeded in redesigning PC herbicides by replacing the oxy-bridge with a carbonyl bridge and the carboxyl group with a sulfonamide group, and synthesized 2Ј-pyrimidinecarbonylsulfonanilides (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and herbicidal activity of sulfonanilides having a pyrimidinyl-containing group at the 2'-position

Yoshimura¹,

Nakatani²,

Asakura

et al. 2011

J. Pestic. Sci.

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The total acreage of rice in Japan in 2009 was 1.62 million ha and most of the paddy fields are mechanically transplanted, using young seedlings grown in nursery boxes.1) It is also noteworthy that most Japanese rice farmers apply so-called one-shot herbicides, which are now essential tools for weed control in paddy fields.2) This has been made possible by the wide variety of one-shot herbicides now available on the Japanese market. While sulfonylurea (SU) herbicides are most commonly used as the active principles in the formulation of one-shot herbicides, because SU herbicides control a wide range of paddy weeds including annual broadleaves and perennial Cyperaceae and about 90% of one-shot herbicides contain 3 to 4 active ingredients. 2)We have so far developed and commercialized our original pyrimidinyl carboxy (PC) herbicides, viz. bispyribac-sodium, pyrithiobac-sodium and pyriminobac-methyl.3-5) These herbicides exhibit their activities by specifically and strongly inhibiting ALS enzyme of plants, which is involved in the biosynthesis of branched-chain amino acids in plants, such as valine, leucine and isoleucine. 6) Because mammals lack ALS enzyme, these herbicides are inherently safe for mammals and, coupled with high activity with low use rates, these PC herbicides are extensively used worldwide as environmentally friendly herbicides.In the course of our researches on PC herbicides, we confirmed that in order for a compound to exhibit high ALS inhibitory activity and high herbicidal activity, the hydrophobic group, pyrimidine ring and acidic group need be placed in a suitable spatial position linked by a suitable spacer group via a suitable linkage group. 7) Based on the findings, we have conducted extensive studies to place various hydrophobic groups and acidic groups in an appropriate position on the pyrimidine ring.PC herbicides have a carboxyl group, but due to their relatively high water solubility as a result of their acidity, PC herSynthesis and herbicidal activity of sulfonanilides having a pyrimidinyl-containing group at the 2-position A novel series of sulfonanilides having a pyrimidinyl-containing group at the 2Ј-position was prepared and their herbicidal activities against paddy weeds and selectivity against rice plants were assessed. The structure-activity relationships were probed by substitution of the sulfonyl group, bridge and benzene ring. Among the sulfonamides, difluoromethyl compound showed comparatively high activity and a broad spectrum to control weeds, including Echinochloa oryzicola. The most preferable substitution position on the benzene ring was in the 6-position and the lower alkyl group showed high herbicidal activity and a broad weed control spectrum, and among the compounds tested, the methoxymethyl group was the best. In respect of the bridge moiety, the hydroxyl group was the best. Among the compounds examined, 2Ј-[(4,6-dimethoxypyrimidin-2-yl)(hydroxy)methyl]-1,1-difluoro-6Ј-(methoxymethyl)methanesulfonanilide, applied at rates between 4 to 16 g a.i./ha, showed excelle...

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“…3 Relatively simple fluoromethane sulfonamides (F 3 CSO 2 NRR or HF 2 CSO 2 NRR) have been shown to possess anti-inflammatory and herbicidal properties. [4][5][6][7] Nevertheless, besides recent studies with carbonic anhydrase, 8, 9 an enzyme known to exhibit a high affinity for a wide range of sulfonamides, such compounds have never been examined as enzyme inhibitors. One possible reason for this was a lack of a facile method for their preparation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a non-hydrolyzable estrone sulfate analogue bearing the difluoromethanesulfonamide group and its evaluation as a steroid sulfatase inhibitor

et al. 2005

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Steroid sulfatase (STS) catalyzes the hydrolyis of steroidal sulfates such as estrone sulfate (ES1) and is considered to be an attractive target in the treatment of steroid dependent cancers. A non-hydrolyzable estrone sulfate (ES1) analogue bearing an alpha,alpha-difluorosulfonamide moiety at the 3-position on the A-ring, compound , was synthesized. Key to the success of this synthesis was the first use of the allyl group as a sulfonamide protecting group. The pK(a) of this ES1 mimic in 0.1 M bis-tris propane, 10% DMSO was determined to be 8.05 using 19F NMR. Compound is a reversible inhibitor with a K(i) similar to that of its sulfonate analogue at pH 7.0. It is more potent than its non-fluorinated sulfonamide analogue and, its inhibitory potency increases with increasing pH, a trend opposite to that of other STS inhibitors. Possible reasons for this are presented.

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Fluoroalkanesulfonanilides, a new class of herbicides

Cited by 18 publications

References 4 publications

Determination of pKa values of fluoroalkanesulfonamides and investigation of their nucleophilicity

Determination of pKa values of fluoroalkanesulfonamides and investigation of their nucleophilicity

Synthesis and herbicidal activity of sulfonanilides having a pyrimidinyl-containing group at the 2'-position

Synthesis of a non-hydrolyzable estrone sulfate analogue bearing the difluoromethanesulfonamide group and its evaluation as a steroid sulfatase inhibitor

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