Trifluoromethylpyridines as Building Blocks for New Agrochemicals

Haga, Takahiro; Tsujii, Yasuhiro; Hayashi, Kouji; Kimura, Fumio; Sakashita, N.; Fujikawa, K.

doi:10.1021/bk-1991-0443.ch009

Cited by 21 publications

(8 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Flazasulfuron degrades rapidly in water and soil by a novel chemical mechanism [70]. For example, its half-life in water is 11 days at 25 DC and 90% of applied ftazasulfuron degrades within 80-100 days at 15 DC in several soils.…”

Section: Flazasulfuronmentioning

confidence: 99%

Recent Advances in Sulfonylurea Herbicides

Brown

Cotterman

1994

Chemistry of Plant Protection

View full text Add to dashboard Cite

The sulfonylurea herbicides were discovered in 1975 and immediately set a new standard for chemical weed control. The subsequent worldwide development effort has led to the commercialization of 18 different active ingredients in over a dozen major crops, and additional development candidates have been announced. Some of the reasons for the rapid commercial acceptance of sulfonylurea herbicides include their exceptionally low application rates (often a factor of 10-100 times lower than conventional herbicides), favorable environmental and toxicological properties, and compatibility with the trend towards postemergence weed control.This chapter reviews recent developments in the biology and biochemistry of the sulfonylurea herbicides. The agricultural utilities of 12 new sulfonylureas commercialized or introduced since 1990 and significant new uses of existing commercial sulfonylureas are reviewed. These include tribenuron methyl, amidosulfuron, and NC330 in wheat and barley; metsulfuron methyl, cinosulfuron, pyrazosulfuron ethyl, and imazosulfuron in rice; rimsulfuron, NC319/MON12000, and CGA 152,005 in maize; and ethametsulfuron methyl, triflusulfuron, flazasulfuron, and rimsulfuron in oilseed rape, sugar beets, turf, and potatoes, respectively. Additionally, the biochemical crop selectivity mechanisms of five sulfonylureas in maize, wheat, and oilseed rape are reviewed. Metabolic reactions involved include aryl and aliphatic hydroxylation and oxidative 0-and N-dealkylation leading to inactivation of herbicidal compounds or selective activation of pro herbicidal sulfonylurea analogs. Finally, current information relating to weed resistance to sulfonylureas is reviewed including occurrence, mechanisms, fitness, gene flow, and management strategies. New developments include, among others, the occurrence of ALS-inhibitor resistant biotypes of aquatic species in U.S. rice production and the appearance of ALSinhibitor resistant biotypes of X anthium strumarium in soybeans. In addition, recent studies of competitiveness, seed production and other fitness comparisons suggest little or no difference in fitness between susceptible and resistant biotypes. Finally, management strategies are described which are designed to preserve the widespread utility of this important class of crop protection tools.

show abstract

Section: Flazasulfuronmentioning

confidence: 99%

Recent Advances in Sulfonylurea Herbicides

Brown

Cotterman

1994

Chemistry of Plant Protection

View full text Add to dashboard Cite

show abstract

“…[38][39][40] Over decades, triuoromethylpyridine ring, a special uorinated nitrogen heterocycle, has been a hot spot for the creation of novel pesticides. [41][42][43] For the period 2000-2017, among a total 166 ISO common name proposals, 10 (6%) contain a tri-uoromethylpyridine, including 3 fungicides, 2 herbicides and 5 insecticides. 43 Our previous works [44][45][46] also revealed that some compounds containing triuoromethyl pyridine showed excellent anti-virus, anti-bacterial and insecticidal activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological activities of novel trifluoromethylpyridine amide derivatives containing sulfur moieties

Guo

Dai

et al. 2020

RSC Adv.

View full text Add to dashboard Cite

show abstract

“…These favorable features of the pyridine derivative are far superior to the corresponding benzene analogue and showed excellent herbicidal activity on perennial grass weeds. 22) As shown in Scheme 5, 2,5-CTF was employed as a key intermediate for the synthesis. Fluazifop-butyl is known to have an asymmetric center on the propionate moiety, with only the (R)-enantiomer being active.…”

Section: Herbicidementioning

confidence: 99%

“…25) Flazasulfuron, which was first reported by ISK in 1986, 26) is a sulfonylurea-type acetolactate synthase (ALS)-inhibiting herbicide that is selective on turf, sugarcane, and perennial crops such as citrus and grape. 22) In the process of evaluating physicochemical and biological properties, it was found that flazasulfuron was readily decomposed and/or metabolized under various conditions through an intramolecular nucleophilic aromatic substitution reaction triggered by the large electronegativity of the trifluoromethyl moiety on the pyridine ring. 27) This observation could be a breakthrough to overcome the carry-over problem with sulfonylurea herbicides and led to the invention of nicosulfuron.…”

Section: Herbicidementioning

confidence: 99%

See 1 more Smart Citation

Synthesis and application of trifluoromethylpyridines as a key structural motif in active agrochemical and pharmaceutical ingredients

et al. 2021

View full text Add to dashboard Cite

Herein, we provide a brief overview of the synthesis and applications of trifluoromethylpyridine (TFMP) and its derivatives in the agrochemical and pharmaceutical industries. Currently, the major use of TFMP derivatives is in the protection of crops from pests. Fluazifopbutyl was the first TFMP derivative introduced to the agrochemical market, and since then, more than 20 new TFMP-containing agrochemicals have acquired ISO common names. Several TFMP derivatives are also used in the pharmaceutical and veterinary industries; five pharmaceutical and two veterinary products containing the TFMP moiety have been granted market approval, and many candidates are currently undergoing clinical trials. The biological activities of TFMP derivatives are thought to be due to the combination of the unique physicochemical properties of the fluorine atom and the unique characteristics of the pyridine moiety. It is expected that many novel applications of TFMP will be discovered in the future.

show abstract

Trifluoromethylpyridines as Building Blocks for New Agrochemicals

Cited by 21 publications

References 0 publications

Recent Advances in Sulfonylurea Herbicides

Recent Advances in Sulfonylurea Herbicides

Synthesis and biological activities of novel trifluoromethylpyridine amide derivatives containing sulfur moieties

Synthesis and application of trifluoromethylpyridines as a key structural motif in active agrochemical and pharmaceutical ingredients

Contact Info

Product

Resources

About