Design and Synthesis of Novel 3,4-Dihydro-2H-1,2,4-benzothiadiazine 1,1-Dioxides-based Strobilurins as Potent Fungicide Candidates

Li, Fengyun; Gong, Jianing; Liu, Jingbo; Li, Yuxin; Li, Zhengming

doi:10.1007/s40242-020-0160-9

Cited by 5 publications

(2 citation statements)

References 29 publications

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“…Another candidate 63 displayed good in vivo activity against E. graminis with 85% inhibition even at 0.2 μg/mL in greenhouse test, close to those of azoxystrobin and trifloxystrobin. Meanwhile, compound 63 possessed 70% and 55% inhibition against P. cubensis at 1.56 and 0.2 μg/mL, respectively, obviously superior to azoxystrobin and trifloxystrobin …”

Section: β-Methoxyacrylate Derivatives As Pesticidesmentioning

confidence: 99%

“…Meanwhile, compound 63 possessed 70% and 55% inhibition against P. cubensis at 1.56 and 0.2 μg/mL, respectively, obviously superior to azoxystrobin and trifloxystrobin. 100 Chen and co-workers developed β-methoxyacrylate derivatives by employing the active 1,2,3-thiadiazole and 3,4dichloroisothiazole scaffolds as side chains. The 1,2,3thiadiazole-based compound 64 displayed remarkable activities against R. cerealis, S. sclerotiorum, and G. zeae with EC 50 values of 0.01, 0.44, and 2.68 μg/mL, respectively, evidently better than positive controls with EC 50 ranging from 0.06 to 15.12 μg/mL.…”

Section: β-Methoxyacrylate Derivatives As Pesticidesmentioning

confidence: 99%

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Comprehensive Overview of β-Methoxyacrylate Derivatives as Cytochrome bc₁ Inhibitors for Novel Pesticide Discovery

Luo

Ning

Rao

2022

J. Agric. Food Chem.

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β-Methoxyacrylate derivatives represent a new class of pesticides, which have attracted increasing attention owing to their unique structure, broad biological activity, and unique mechanisms of action. They inhibit mitochondrial respiration via preventing electron transfer at the Qo site of the cytochrome bc 1 complex and thus are identified as cyt bc 1 inhibitors. A variety of βmethoxyacrylate derivatives have been reported by many research groups for discovery of novel pesticides with improved expected activities. This review focuses on development of β-methoxyacrylate derivatives with great significance as pesticides such as fungicides, acaricides, insecticides, herbicides, and antiviral agents. In addition, the structure−activity relationships (SARs) of βmethoxyacrylate derivatives are summarized. Moreover, the cause of resistance to β-methoxyacrylate fungicides and some solutions are also introduced. Finally, the development trend of β-methoxyacrylate derivatives as pesticides is explored. We hope the review will give a guide to develop novel β-methoxyacrylate pesticides in the future.

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Section: β-Methoxyacrylate Derivatives As Pesticidesmentioning

confidence: 99%

Section: β-Methoxyacrylate Derivatives As Pesticidesmentioning

confidence: 99%

Comprehensive Overview of β-Methoxyacrylate Derivatives as Cytochrome bc₁ Inhibitors for Novel Pesticide Discovery

Luo

Ning

Rao

2022

J. Agric. Food Chem.

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Synthesis and thermal safety assessment of methyl (αE)-2-(bromomethyl)-α-(methoxyimino)benzeneacetate

Yu,

Zhu,

et al. 2024

Process Safety and Environmental Protection

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Nickel Pincer Complexes Catalyzed Sustainable Synthesis of 3,4-Dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxides via Acceptorless Dehydrogenative Coupling of Primary Alcohols

Pennamuthiriyan,

Rengan

2024

J. Org. Chem.

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We report the atom-economic and sustainable synthesis of biologically important 3,4-dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxide (DHBD) derivatives from readily available aromatic primary alcohols and 2-aminobenzenesulfonamide catalyzed by nickel(II)-N∧N∧S pincer-type complexes. The synthesized nickel complexes have been well-studied by elemental and spectroscopic (FT-IR, NMR, and HRMS) analyses. The solidstate molecular structure of complex 2 has been authenticated by a single-crystal X-ray diffraction study. Furthermore, a series of 3,4dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxide derivatives have been synthesized (24 examples) utilizing a 3 mol % Ni(II) catalyst through acceptorless dehydrogenative coupling of benzyl alcohols with benzenesulfonamide. Gratifyingly, the catalytic protocol is highly selective with the yield up to 93% and produces eco-friendly water/hydrogen gas as byproducts. The control experiments and plausible mechanistic investigations indicate that the coupling of the in situ generated aldehyde with benzenesulfonamide leads to the desired product. In addition, a large-scale synthesis of one of the thiadiazine derivatives unveils the synthetic usefulness of the current methodology.

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Design and Synthesis of Novel 3,4-Dihydro-2H-1,2,4-benzothiadiazine 1,1-Dioxides-based Strobilurins as Potent Fungicide Candidates

Cited by 5 publications

References 29 publications

Comprehensive Overview of β-Methoxyacrylate Derivatives as Cytochrome bc₁ Inhibitors for Novel Pesticide Discovery

Comprehensive Overview of β-Methoxyacrylate Derivatives as Cytochrome bc₁ Inhibitors for Novel Pesticide Discovery

Synthesis and thermal safety assessment of methyl (αE)-2-(bromomethyl)-α-(methoxyimino)benzeneacetate

Nickel Pincer Complexes Catalyzed Sustainable Synthesis of 3,4-Dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxides via Acceptorless Dehydrogenative Coupling of Primary Alcohols

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Design and Synthesis of Novel 3,4-Dihydro-2H-1,2,4-benzothiadiazine 1,1-Dioxides-based Strobilurins as Potent Fungicide Candidates

Cited by 5 publications

References 29 publications

Comprehensive Overview of β-Methoxyacrylate Derivatives as Cytochrome bc1 Inhibitors for Novel Pesticide Discovery

Comprehensive Overview of β-Methoxyacrylate Derivatives as Cytochrome bc1 Inhibitors for Novel Pesticide Discovery

Synthesis and thermal safety assessment of methyl (αE)-2-(bromomethyl)-α-(methoxyimino)benzeneacetate

Nickel Pincer Complexes Catalyzed Sustainable Synthesis of 3,4-Dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxides via Acceptorless Dehydrogenative Coupling of Primary Alcohols

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Product

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Comprehensive Overview of β-Methoxyacrylate Derivatives as Cytochrome bc₁ Inhibitors for Novel Pesticide Discovery

Comprehensive Overview of β-Methoxyacrylate Derivatives as Cytochrome bc₁ Inhibitors for Novel Pesticide Discovery