Discovery of (2-benzoylethen-1-ol)-containing 1,2-benzothiazine derivatives as novel 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibiting-based herbicide lead compounds

Lei, Kang; Hua, Xuewen; Tao, Yuanyuan; Liu, Yang; Liu, Na; Ma, Yangmin; Li, Yonghong; Xu, Xinhua; Kong, Chui‐Hua

doi:10.1016/j.bmc.2015.11.032

Cited by 46 publications

(36 citation statements)

References 41 publications

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“…Allelochemicals may act as leads for new herbicide discovery . The benzothiazine derivative, originating from the rice allelochemical tricin, was identified as an allelochemical‐based herbicide . However, determination of herbicidal efficacy and rice safety in paddy systems was needed.…”

Section: Discussionmentioning

confidence: 99%

“…It is not surprising that the benzothiazine derivative has no toxic effects on zebrafish and earthworms. The benzothiazine derivative is a HPPD‐inhibiting compound that inhibits weeds through interference with photosynthetic processes . HPPD is an important enzyme in the tyrosine metabolic pathway, leading to plastoquinone (PQ) synthesis.…”

Section: Discussionmentioning

confidence: 99%

“…Therefore, as an ideal lead allelochemical for new herbicide discoveries, tricin has been a major focus of allelochemical‐based herbicides. A series of tricin‐derived compounds including aurones, 3‐benzoyl‐4‐hydroxylcoumarins and (2‐benzoylethen‐1‐ol)‐containing benzothiazine derivatives have been synthesized . Several (2‐benzoylethen‐1‐ol)‐containing 1, 2‐benzothiazine derivatives showed good pre‐emergent activity against weeds by inhibiting 4‐hydroxyphenylpyruvate dioxygenase (HPPD) .…”

Section: Introductionmentioning

confidence: 99%

“…A series of tricin‐derived compounds including aurones, 3‐benzoyl‐4‐hydroxylcoumarins and (2‐benzoylethen‐1‐ol)‐containing benzothiazine derivatives have been synthesized . Several (2‐benzoylethen‐1‐ol)‐containing 1, 2‐benzothiazine derivatives showed good pre‐emergent activity against weeds by inhibiting 4‐hydroxyphenylpyruvate dioxygenase (HPPD) . Among them, a benzothiazine derivative 3‐(2‐chloro‐4‐methanesulfonyl)‐benzoyl‐4‐hydroxy‐2‐methyl‐2H‐ 1,2‐benzothiazine‐1,1‐dioxide effectively inhibited the growth of barnyardgrass ( Echinochloa crus‐galli ) at low concentrations through interference with photosynthetic performance .…”

Section: Introductionmentioning

confidence: 99%

“…[14][15][16] Several (2-benzoylethen-1-ol)-containing 1, 2-benzothiazine derivatives showed good pre-emergent activity against weeds by inhibiting 4-hydroxyphenylpyruvate dioxygenase (HPPD). 16 Among them, a benzothiazine derivative 3-(2-chloro-4-methanesulfonyl)-benzoyl-4-hydroxy-2-methyl-2H-1,2-benzothiazine-1,1-dioxide effectively inhibited the growth of barnyardgrass (Echinochloa crus-galli) at low concentrations through interference with photosynthetic performance. 17 Therefore, the benzothiazine derivative was patented as an allelochemical-based herbicide in China.…”

Section: Introductionmentioning

confidence: 99%

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Herbicidal efficacy and ecological safety of an allelochemical‐based benzothiazine derivative

Zhao

Kong

2019

Pest Management Science

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Background The development of allelochemical‐based herbicides may be of particular value for weed management in cropping systems. However, the action of potential allelochemical‐based herbicides on crop selectivity and ecotoxicology needs to be clarified before they can be introduced into cropping systems. Results An allelochemical‐based 3‐(2‐chloro‐4‐ethanesulfonyl)‐benzoyl‐hydroxy‐2‐ methyl‐2H‐1,2‐benzothiazine‐1,1‐dioxide, originating from the rice allelochemical tricin, was applied to a paddy system. The benzothiazine derivative could effectively control dominant weeds, while rice was not affected at rates of 75–100 g a.i. ha−1. Furthermore, this target compound significantly inhibited the growth of all weeds tested with excellent selectivity for maize; however, it was not safe for soybean. The benzothiazine derivative had no toxic effects on zebrafish and earthworms. The benzothiazine derivative was rapidly degraded in soil with half‐lives of 17.51–20.47 days. MiSeq‐pyrosequencing revealed relative safety to soil microorganisms at 5 mg kg−1 of the benzothiazine derivative. Conclusion The allelochemical‐based benzothiazine derivative at optimal application rates can be recommended to provide satisfactory control of paddy weeds. The benzothiazine derivative with excellent crop selectivity and ecological safety may be further developed for weed management in maize fields. © 2019 Society of Chemical Industry

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Herbicidal efficacy and ecological safety of an allelochemical‐based benzothiazine derivative

Zhao

Kong

2019

Pest Management Science

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N‐Heterocyclic Carbene Organocatalyzed [3+3] Annulation for the Enantioselective Synthesis of Benzopyranothiazinones

Mroczyńska,

Rafiński

2024

Adv Synth Catal

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The design, inspired by the core‐structure of oxicam has allowed the enantioselective synthesis of benzopyranothiazinone motifs employing N‐heterocyclic carbene (NHC) catalysis. The NHC‐mediated transformation involves the reaction of α,β‐unsaturated aldehydes with suitable substituted benzothiazinone derivatives. This process encompasses the initial formation of α,β‐unsaturated acylazoliums from ynals and concurrent generation of enolates from benzothiazinone. The culmination of these reactions results in an efficient annulation, yielding the desired products with reasonable yields and high stereoselectivities. This study underscores the potential of NHC catalysis in the streamlined synthesis of complex heterocyclic structures.

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Mesotrione Herbicide: Efficiency, Effects, and Fate in the Environment after 15 Years of Agricultural Use

Carles

Joly

2017

CLEAN Soil Air Water

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Mesotrione (2‐[4‐(methylsulfonyl)‐2‐nitrobenzoyl]‐cylohexane‐1,3‐dione) is an herbicide brought to the market 15 years ago and commonly used on maize cultures. This review summarizes the results obtained from worldwide scientific studies on its efficiency, effects, and fate in environment, in order to bring first overall conclusions about its safety of use. The comprehensive review of the available scientific literature reveals that mesotrione applied as recommended ensures the desired effects on sensitive crops, mainly in post‐emergence application, while exhibiting favorable toxicological, and environmental profile. According to the studies realized so far, mesotrione presents no significant risks to humans and other non‐target organisms or to the environment. Its degradation by soil microorganisms is fast, ensuring a low possibility to retrieve mesotrione in ground water. Its terminal residues in soil, maize, grain, and maize straw are below the limit of quantification. All these results suggest that mesotrione applied as directed ensures the respect of current environmental standards and food safety. Future prospects should focus on its associated pesticides when applied in mixtures on field, and on the detection, quantification, and risk assessment of its transformation products in order to exclude any toxicological synergistic effects.

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Discovery of (2-benzoylethen-1-ol)-containing 1,2-benzothiazine derivatives as novel 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibiting-based herbicide lead compounds

Cited by 46 publications

References 41 publications

Herbicidal efficacy and ecological safety of an allelochemical‐based benzothiazine derivative

Herbicidal efficacy and ecological safety of an allelochemical‐based benzothiazine derivative

N‐Heterocyclic Carbene Organocatalyzed [3+3] Annulation for the Enantioselective Synthesis of Benzopyranothiazinones

Mesotrione Herbicide: Efficiency, Effects, and Fate in the Environment after 15 Years of Agricultural Use

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