Recent developments in fluorine‐containing pesticides

Pest Management Science, Journal Year: 2023, Volume and Issue: 80(7), P. 3065 - 3087

Published: Dec. 11, 2023

To ensure ongoing sustainability, the modern agrochemical industry is faced with enormous challenges. These arise from provision of high-quality food to increasing water use and environmental impact as well a growing world population. The loss previous agrochemicals due consumer perception, changing grower needs ever-changing regulatory requirements higher than number active ingredients that are being introduced into crop protection market. Therefore, development novel essential provide improved efficacy profiles. In this context, introduction fluorine atoms fluorine-containing motifs molecule an important method influence its physicochemical properties. include, for example, small difluoro- trifluoromethyl, or trifluoromethoxy groups at aryl heterocyclic moieties but also fragments like 2,2,2-trifluoroethoxycarbonyl, trifluoromethylsulfonyl, trifluoroacetyl, so far unusal rest heptafluoro-iso-propyl. This review gives overview recent developments pesticides launched over past 7 years describes selection current candidates. © 2023 Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf Society Chemical Industry.

Language: Английский

---

Design, Synthesis, and Antifungal Activities of Novel Pyrazole-4-carboxamide Derivatives Containing an Ether Group as Potential Succinate Dehydrogenase Inhibitors

Journal of Agricultural and Food Chemistry, Journal Year: 2023, Volume and Issue: 71(24), P. 9255 - 9265

Published: June 7, 2023

A series of novel pyrazole-4-carboxamides bearing an ether group were designed and synthesized on the basis structure commercial succinate dehydrogenase inhibitor (SDHI) fungicide flubeneteram via scaffold hopping evaluated for their antifungal activities against five fungi. The bioassay results showed that most target compounds exhibited excellent in vitro activity Rhizoctonia solani some exerted remarkable Sclerotinia sclerotiorum, Botrytis cinerea, Fusarium graminearum, Alternaria alternate. Particularly, 7d 12b displayed outstanding R. solani, with EC50 value 0.046 μg/mL, far superior to boscalid (EC50 = 0.741 μg/mL) fluxapyroxad 0.103 μg/mL). Meanwhile, compound also presented a broader fungicidal spectrum than other compounds. Moreover, vivo anti-R. could significantly inhibit growth rice leaves protective curative efficacies. In addition, (SDH) enzymatic inhibition assay generated significant SDH inhibition, IC50 3.293 μM, which was about 2 times better (IC50 7.507 μM) 5.991 μM). Furthermore, scanning electron microscopy (SEM) analysis indicated destroyed typical morphology hyphae. molecular docking study revealed embed into binding pocket form hydrogen bond interactions TRP173 TRY58 at site SDH, line fluxapyroxad, indicating they had similar mechanism action. These demonstrated be promising candidates SDHI fungicides, deserved further investigation.

Language: Английский

---

Discovery and Mechanism of a Nematicide Candidate (W3): A Novel Amide Compound Containing a Cyclopropyl Moiety

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(11), P. 5585 - 5594

Published: March 5, 2024

To find novel nematicides, we screened the nematicidal activity of compounds in our laboratory compound library. Interestingly,

Language: Английский

---

Fluopyram analogues containing an indole moiety: synthesis, biological activity and molecular docking study

Molecular Diversity, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 20, 2025

Language: Английский

---

A Study in Scaffold Hopping: Discovery and Optimization of Thiazolopyridines as Potent Herbicides That Inhibit Acyl-ACP Thioesterase

Journal of Agricultural and Food Chemistry, Journal Year: 2023, Volume and Issue: 71(47), P. 18212 - 18226

Published: Sept. 7, 2023

In the search for new chemical entities that can control resistant weeds by addressing novel modes of action (MoAs), we were interested in further exploring a compound class contained 1,8-naphthyridine core. By leveraging scaffold hopping methodologies, able to discover thiazolopyridine act as potent herbicidal molecules. Further biochemical investigations allowed us identify thiazolopyridines inhibit acyl-acyl carrier protein (ACP) thioesterase (FAT), with this being confirmed via an X-ray cocrystal structure. Greenhouse trials revealed display excellent grass weed species pre-emergence application coupled dose response windows enable partial selectivity certain crops.

Language: Английский

---

Novel amide derivatives containing azetidine moiety as potential SDH inhibitors: Design, synthesis, and evaluation of bioactivity

Journal of Saudi Chemical Society, Journal Year: 2024, Volume and Issue: 28(3), P. 101853 - 101853

Published: April 5, 2024

Fluopyram is a highly effective agricultural fungicide targeting succinate dehydrogenase (SDH). Twenty-six novel amide derivatives containing azetidine were designed and synthesized with fluopyram as the lead, their biological activities tested. The results showed that some compounds had obvious antifungal against Phomopsis sp., among them, EC50 value of compound C24 was 5.7 mg/L, which significantly better than (105.4 mg/L). curative protective on kiwi fruit infected sp. 42.2 52.9 %, (30.4 35.6 %) at 200 mg/L. Moreover, exhibited excellent inhibitory SDH. scanning electron microscopy (SEM) indicated mycelium collapsed or even ruptured after treatment. Meanwhile, molecular docking deeply embedded into SDH binding pocket, model stabilized by cation–π interaction Cys-40, Tyr-58 an H-bond Lys-455 Asn-452. Compound can provide valuable idea to find new inhibitors.

Language: Английский

---

Recent innovations in crop protection research

Pest Management Science, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 30, 2024

Abstract As the world's population continues to grow and demand for food increases, agricultural industry faces challenge of producing higher yields while ensuring safety quality harvests, operators, consumers. The emergence resistance, pest shifts, stricter regulatory requirements also urgently calls further advances in crop protection discovery new innovative products sustainable protection. This study reviews recent highlights innovation as presented at 15th IUPAC International Congress Crop Protection Chemistry held New Delhi, 2023. following are discussed: insecticides Indazapyroxamet, Dimpropyridaz Fenmezoditiaz, fungicides Mefentrifluconazole Pyridachlomethyl, nematicide Cyclobutrifluram, herbicides Rimisoxafen, Dimesulfazet, Epyrifenacil well abiotic stress management product Anisiflupurin. In addition, latest research areas all will be presented, including insecticidal alkyl sulfones 1,3,4‐trisubstituted pyrazoles, fungicidal picolinamides, herbicidal ketoenols, trifluoromethylpyrazoles, enhancement green control research. © 2024 Author(s). Pest Management Science published by John Wiley & Sons Ltd on behalf Society Chemical Industry.

Language: Английский

---

Structure-Based Virtual Screening of Natural Products and Optimization for the Design and Synthesis of Novel CeCht1 Inhibitors as Nematicide Candidates

Journal of Agricultural and Food Chemistry, Journal Year: 2022, Volume and Issue: 71(1), P. 244 - 254

Published: Dec. 29, 2022

Nematode chitinases are critical components of the nematode life cycle, and CeCht1 is a potential target for developing novel nematicides. Herein, lunidonine, natural quinoline alkaloid, was first discovered to have inhibitory activity against CeCht1, which acquired from library over 16,000 products using structure-based virtual screening methodology. A pocket-based lead optimization strategy employed based on predicted binding mode lunidonine. Subsequently, series benzo[d][1,3]dioxole-5-carboxylate derivatives were designed synthesized, their activities as well in vitro nematicidal Caenorhabditis elegans assessed. The analysis structure-activity relationship mechanisms provided insights into interactions with active site, could facilitate future research improving potency activity. Especially, compound a12 interacted exhibited excellent C. LC50 value 41.54 mg/L, suggesting that it be promising candidate chemical nematicide targeting CeCht1. known modes structural features these inhibitors will contribute design stronger CeCht1-based nematicides control nematodes agriculture.

Language: Английский

---

Design, Synthesis, and Properties of Silicon-Containing meta-Diamide Insecticides

Journal of Agricultural and Food Chemistry, Journal Year: 2023, Volume and Issue: 71(47), P. 18188 - 18196

Published: May 16, 2023

Silicon-containing compounds are sporadically used in crop protection and drug discovery have demonstrated to increase the biological efficacy as well reduce toxicity, improve physicochemical properties, favorably impact environmental profile. As part of our research, we investigated application bioisosteric silicon replacements meta-diamide insecticides studied activity molecular properties corresponding novel compounds. At all meaningful structural elements meta-diamides, silicon-containing substituents were introduced synthetic methodology was developed for their syntheses. most promising compound, II-18 emerged, which exhibits a very low LC50 value 2.00 mg/L against Mythimna separata compares reference 28 (LC50 = 0.17 mg/L) II-20 0.27 mg/L). Our research on once again confirmed that can be beneficially affected by insertion silicone introduction well-chosen motifs is an excellent strategy agrochemical research.

Language: Английский

---

A New Class of Diaryl Ether Herbicides: Structure–Activity Relationship Studies Enabled by a Rapid Scaffold Hopping Approach

Journal of Agricultural and Food Chemistry, Journal Year: 2023, Volume and Issue: 71(47), P. 18171 - 18187

Published: June 23, 2023

We report on the development of a novel class diaryl ether herbicides. After discovery phenoxybenzoic acid with modest herbicidal activity, optimization led to several molecules improved control broadleaf and grass weeds. To facilitate this process, we first employed three-step combinatorial approach, then pivoted one-step Ullmann-type coupling that provided faster access new analogs. determining primary target site our benchmark ethers was acetolactate synthase (ALS), further leveraged copper-catalyzed methodology conduct scaffold hopping campaign in hope uncovering an additional mode action fewer documented cases resistance. Our comprehensive systematic investigation revealed while activity area seems be exclusively linked ALS inhibition, represent structurally distinct Group 2 The structure-activity relationships us conclusion are described herein.

Language: Английский

---