1,1-Diaryl compounds as important bioactive module in pesticides

Xiao, Yumei; Li, Jiaqi; Fu, Bin; Qin, Z. H.

doi:10.1007/s11030-018-9895-3

Cited by 25 publications

(22 citation statements)

References 89 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The first-generation pyrazole-type HPPD inhibitors, such as pyrazolinate, pyrazoxyfen, and benzofenap (Figure ), were mainly used to control weeds in the rice fields with application rates up to 4 kg of active ingredient (ai)/ha. , After HPPD was identified as the action target of these herbicides, structure-based discovery of novel HPPD inhibitors has become a hot area for pesticide chemists worldwide and has produced second-generation pyrazole-type HPPD inhibitors with significantly reduced application rates, including topramezone, pyrasulfotole, and tolpyralate. − However, these products are mainly used for the weed control of corn and cereal fields, and new HPPD-inhibiting herbicides for other crops are of great urgency as a result of the rapid development of weed resistance …”

Section: Introductionmentioning

confidence: 99%

Discovery of Novel Pyrazole–Quinazoline-2,4-dione Hybrids as 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

et al. 2020

J. Agric. Food Chem.

View full text Add to dashboard Cite

4-Hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) has been identified as one of the most significant targets in herbicide discovery for resistant weed control. In a continuing effort to discover potent novel HPPD inhibitors, we adopted a ring-expansion strategy to design a series of novel pyrazole−quinazoline-2,4-dione hybrids based on the previously discovered pyrazole−isoindoline-1,3-dione scaffold. One compound, 3-(2-chlorophenyl)-6-(5-hydroxy-1,3-dimethyl-1H-pyrazole-4-carbonyl)-1,5-dimethylquinazoline-2,4(1H,3H)-dione (9bj), displayed excellent potency against AtHPPD, with an IC 50 value of 84 nM, which is approximately 16-fold more potent than pyrasulfotole (IC 50 = 1359 nM) and 2.7-fold more potent than mesotrione (IC 50 = 226 nM). Furthermore, the co-crystal structure of the AtHPPD−9bj complex (PDB ID 6LGT) was determined at a resolution of 1.75 Å. Similar to the existing HPPD inhibitors, compound 9bj formed a bidentate chelating interaction with the metal ion and a π−π stacking interaction with Phe381 and Phe424. In contrast, o-chlorophenyl at the N3 position of quinazoline-2,4-dione with a double conformation was surrounded by hydrophobic residues (Met335, Leu368, Leu427, Phe424, Phe392, and Phe381). Remarkably, the greenhouse assay indicated that most compounds displayed excellent herbicidal activity (complete inhibition) against at least one of the tested weeds at the application rate of 150 g of active ingredient (ai)/ha. Most promisingly, compounds 9aj and 9bi not only exhibited prominent weed control effects with a broad spectrum but also showed very good crop safety to cotton, peanuts, and corn at the dose of 150 g of ai/ha.

show abstract

Section: Introductionmentioning

confidence: 99%

Discovery of Novel Pyrazole–Quinazoline-2,4-dione Hybrids as 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

et al. 2020

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

“…The so‐called plug‐in molecule is a class of molecules defined by us, which is a pharmacodynamic cluster occurring in bioactive compounds with high frequency and functioned by an easily derivatized group. Both diaryl ketones and aryl ethanones are excellent plug‐in molecules for the discovery of novel agrochemicals . Using this strategy, compounds 1 and 2 react with hydroxylamine hydrochloride to generate oximes 3 and 4 respectively (see Appendix for the preparation method and structural characterization data).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and herbicidal activity against barnyard grass of novel diarylmethanone O‐(2,6‐bis((4,6‐dimethoxypyrimidin‐2‐yl)oxy)benzoyl)oximes

Xiang

Zhang

et al. 2020

Pest Management Science

Self Cite

View full text Add to dashboard Cite

BACKGROUND: Pyribenzoxim is an excellent herbicide that can effectively control barnyard grass. However, there are few reports of its structural analogs and structure-activity relationship (SAR), which makes pyribenzoxim an isolated case. Here, a series of diarylmethanone oxime esters characterized by pyridine heterocycles were designed and synthesized for herbicidal screening and SAR investigation against barnyard grass.RESULTS: At greenhouse treatment concentrations of 1.17-37.5 ∼g mL −1 , the title compounds showed a positive dosetoxicity correlation toward barnyard grass plants, with the damage becoming progressively more serious over time. At a concentration of 18.75 ∼g mL −1 and above, obvious damage was observed in 3 days, most plants died in 7 days, and all died in 14 days. Different degrees of damage were also seen when the concentration was lower than 9.38 ∼g mL −1 . The selected compounds 5-20 and 5-21 showed excellent control against Echinochloa crusgalli (L.) Beauv., Leptochloa chinensis (L.) Nees, Cyperus difformis L. and Lindernia procumbens (Krock.) Philcox in paddy fields, which was slightly better than that of pyribenzoxim.CONCLUSION: SAR analysis of greenhouse data revealed that the type and position of substituents on aromatic rings greatly influenced the activity of the compounds, although log P values showed no obvious correlation with activity. Combined with compounds 5-20 and 5-21, which showed moderate and excellent activity in greenhouse experiments, and excellent activity in controlling barnyard grass in the field, we conclude that pyribenzoxim analogs probably act as prodrugs, and this could be a focus of attention in future studies on structural optimization of the herbicide. L Xiang et al.wileyonlinelibrary.com/journal/ps *CD, Cyperus difformis L.; EC, Echinochloa crusgalli (L.) Beauv.; LC, Leptochloa chinensis (L.) Nees; LP, Lindernia procumbens (Krock.) Philcox. †Significant difference at 5% level. In the abcde label below, those with the same letters show no significant difference, but the others are significant. synthesis and herbicidal activity against barnyard grass of novel pyribenzoxim analogues

show abstract

“…Chromatography refers to flash silica gel column chromatography (0.060−0.200 mm (60 Å) silica gel from Sorbent Technology was used as the stationary phase). 1 H NMR and 13 C NMR spectra were recorded at room temperature in DMSO-d 6 and CDCl 3 on a Bruker 400 or 400 MHz instrument operating at 300 MHz. 1 H chemical shifts were referenced to the DMSO solvent signal (2.48 ppm).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…1 H NMR and 13 C NMR spectra were recorded at room temperature in DMSO-d 6 and CDCl 3 on a Bruker 400 or 400 MHz instrument operating at 300 MHz. 1 H chemical shifts were referenced to the DMSO solvent signal (2.48 ppm). 13 C chemical shifts were referenced to the DMSO solvent signal (40.00 ppm).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…9b,11 To advance this synthetic approach, a convenient method for preparation of the N-Boc-3-aryl-3-azetidinol precursors was needed. As illustrated in Scheme 2, commercially available N-Boc-3-azetidinone (1) was readily converted into the corresponding N-Boc-3-aryl-3-azetidinols 2 by nucleophilic addition at the ketone moiety using aryllithium reagents. 12 The aryllithium reagents were generated in situ from the corresponding aryl bromides upon treatment with nbutyllithium.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Simple 3,3-Diarylazetidines from N-Boc-3-arylazetidinols Using Friedel–Crafts Arylation Conditions

Das

Weissenfluh

et al. 2020

J. Org. Chem.

View full text Add to dashboard Cite

A synthesis of 3,3-diarylazetidines from N-Boc-3-aryl-3-azetidinols using Friedel–Crafts arylation conditions with AlCl3 is described. A series of substituted diarylazetidines were readily prepared and isolated as the oxalate salts in high yield and high purity. The 3,3-diarylazetidine oxalates were then easily converted into N-alkyl and N-acyl analogues (RX, NaHCO3/DMF/100 °C) in high overall yields.

show abstract

1,1-Diaryl compounds as important bioactive module in pesticides

Cited by 25 publications

References 89 publications

Discovery of Novel Pyrazole–Quinazoline-2,4-dione Hybrids as 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

Discovery of Novel Pyrazole–Quinazoline-2,4-dione Hybrids as 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

Synthesis and herbicidal activity against barnyard grass of novel diarylmethanone O‐(2,6‐bis((4,6‐dimethoxypyrimidin‐2‐yl)oxy)benzoyl)oximes

Synthesis of Simple 3,3-Diarylazetidines from N-Boc-3-arylazetidinols Using Friedel–Crafts Arylation Conditions

Contact Info

Product

Resources

About