Design, synthesis, and evaluation of novel isoxazoline derivatives containing 2-phenyloxazoline moieties as potential insecticides.

Isoxazoline insecticides have shown broad-spectrum insecticidal activity against a variety of insect pests. However, the high toxicity of isoxazoline compounds towards honeybees restricts their application in crop protection. To mitigate this issue, a series of isoxazoline derivatives containing 2-phenyloxazoline were designed and synthesized.

Discovery of new N-Phenylamide Isoxazoline derivatives with high insecticidal activity and reduced honeybee toxicity.

Isoxazoline is a novel structure with strong potential for controlling agricultural insect pests, but its high toxicity to honeybees limits its development in agriculture. Herein, a series of N-phenylamide isoxazoline derivatives with low honeybee toxicity were designed and synthesized using the intermediate derivatization method. Bioassay results showed that these compounds exhibited good insecticidal activity.

Discovery of Arylfluorosulfates as Novel Fungicidal Agents against Plant Pathogens.

A series of arylfluorosulfates were synthesized as fungicide candidates through a highly efficient sulfur fluoride exchange (SuFEx) reaction. A total of 32 arylfluorosulfate derivatives with simple structures have been synthesized, and most of them exhibited fungal activities against five agricultural pathogens (, , , , and ). Among the target compounds, compound exhibited great antifungal activity against (EC = 1.

Rational Design of Insecticidal Isoxazolines Containing Sulfonamide or Sulfinamide Structure as Antagonists of GABA Receptors with Reduced Toxicities to Honeybee and Zebrafish.

To develop highly effective, nontarget organism-friendly insecticides based on the isoxazoline scaffold, we rationally designed and synthesized 25 isoxazoline derivatives containing sulfonamides and sulfinamides. Their insecticidal activities against the diamondback moth (), fall armyworm (), beet armyworm (), and Fabricius () were evaluated. The trifluoromethyl sulfinamide-containing compound displayed excellent activities with LC values being 0.

Bruceine D Acts as a Potential Insecticide by Antagonizing 20E-EcR/USP Signal Transduction.

Bruceine D (BD) is an effective insecticidal compound found in the Chinese herb (L.) Merr. BD inhibits the growth and metamorphosis of and ; however, its target protein and the molecular mechanism of insecticidal activity remain unclear.

Design, synthesis, insecticidal activities and translocation of amino acid-tralopyril conjugates as vectorizing agrochemicals.

Background: Conjugating amino acid moieties to active ingredients has been recognized as an effective method for improving the precise targeting of the active form to the specific site. Based on the vectorization strategy, a series of amino acid-tralopyril conjugates were designed and synthesized as novel proinsecticide candidates, with the potential capability of root uptake and translocation to the foliage of crops.

Results: Bioassay results showed excellent insecticidal activities of some conjugates, in particular, the conjugates 6b, 6e, and 7e, against the diamondback moth (Plutella xylostella), with equivalent insecticidal activity to chlorfenapyr (CFP).

Mode of Action of Novel Pyrazoloquinazoline on Diamondback Moth () Ligand-Gated Chloride Channels.

In our previous study, a series of novel pyrazoloquinazolines were synthesized. Pyrazoloquinazoline showed high insecticidal activity against the diamondback moth () and no cross-resistance to fipronil. Patch clamp electrophysiology performed on pupae brains and two-electrode voltage clamp electrophysiology performed on oocytes indicated that might act on the ionotropic γ-aminobutyric acid (GABA) receptor (GABAR) and glutamate-gated chloride channel (GluCl).

Azocalixarene-Based Supramolecular System for the Detection of Paraquat via an Improved Indicator Displacement Assay.

In view of the lethal toxicity of paraquat (PQ) on human health, herein, a simple indicator displacement assay (IDA) based on an azo-modified calixarene host (azoCX[4]) and a fluorophore guest (-DPD) were elaborately constructed for PQ detection in environmental water samples and plant surfaces. The fluorescent signal of -DPD in the probe can be quenched by azoCX[4] through a photon-induced electron transfer process and recovered upon the addition of PQ within 10 s. The detection range of the -DPD@azoCX[4] probe was calculated to be 0.

Design, synthesis, and biological activity of novel spiro-pyrazolo[1,5-a]quinazolines derivatives as potential insecticides.

Background: Arylpyrazole insecticides display broad-spectrum insecticidal activity against insect pests. However, the high toxicity toward honeybees associated with fipronil prohibits its agronomic utility. To explore reducing the toxicity of aryl pyrazole analogs to bees, a series of new spiro-pyrazolo[1,5-a]quinazoline derivatives were designed and synthesized.

General Method for Pesticide Recognition Using Albumin-Based Host-Guest Ensembles.

The massive use of pesticides nowadays has led to serious consequences for the environment and public health. Fluorescence analytical methods for pesticides are particularly advantageous with respect to simplicity and portability; however, currently available fluorescence methods (enzyme-based assays and indicator displacement assays) with poor universality are only able to detect few specific pesticides (., organophosphorus).

Diversity-Oriented Synthesis of Fluoromethylated Arenes via Palladium-Catalyzed C-H Fluoromethylation of Aryl Iodides.

Herein we report the first versatile and expeditious method for the site-selective C-H fluoromethylation of aryl iodides via Pd/norbornene cooperative catalysis, which could work as a robust toolbox for the diversity-oriented synthesis (DOS) of fluoromethylated arenes. This methodology features the use of the low-cost industrial raw material CHIF as the fluoromethyl source, an excellent functional group tolerance, and a broad termination scope and can be expanded to the late-stage modification of biorelevant molecules.

Overexpression of AtAAP1 increased the uptake of an alanine-chlorantraniliprole conjugate in Arabidopsis thaliana.

Transporters play an important role in the uptake and redistribution of agrochemicals to the site of insect feeding. The product of the Arabidopsis thaliana gene AtAAP1 substantially contributes to inorganic nitrogen acquisition under ecologically relevant amino acid concentrations. Here, the transporter ability of AtAAP1 to a chlorantraniliprole-alanine conjugate (CAP-Ala-1) was tested both in planta and in vitro.

DMSO-mediated palladium-catalyzed cyclization of two isothiocyanates C-H sulfurization: a new route to 2-aminobenzothiazoles.

DMSO was found to activate arylisothiocyanates for self-nucleophilic addition. A subsequent intramolecular C-H sulfurization catalyzed by PdBr enables access to a wide range of 2-aminobenzothiazole derivatives in moderate to good yields. This is the first example of a DMSO-mediated Pd-catalyzed synthesis of 2-aminobenzothiazoles through cyclization/C-H sulfurization of two isothiocyanates.

HFIP-Promoted Bischler Indole Synthesis under Microwave Irradiation.

1,1,1,3,3,3-Hexafluoropropan-2-ol (HFIP) was found to be effective for the Bischler indole synthesis under microwave irradiation in the absence of a metal catalyst. Under the catalysis of HFIP, a wide range of α-amino arylacetones were successfully transformed into indole derivatives with moderate to good yields.

AtLHT1 Transporter Can Facilitate the Uptake and Translocation of a Glycinergic-Chlorantraniliprole Conjugate in Arabidopsis thaliana.

Understanding of the transporters involved in the uptake and translocation of agrochemicals in plants could provide an opportunity to guide pesticide to the site of insect feeding. The product of Arabidopsis thaliana gene AtLHT1 makes a major contribution to the uptake into the roots of free amino acids and some of their derivatives. Here, a chlorantraniliprole-glycine conjugate (CAP-Gly-1) was tested for its affinity to AtLHT1 both in planta and in vitro.

Novel amino acid ester-chlorantraniliprole conjugates: design, synthesis, phloem accumulation and bioactivity.

Background: Conjugating amino acid and glucose fragments with existing pesticide structures has been shown to be an effective way to introduce phloem mobility into non-phloem mobile species. However, the resulting derivatives always suffer from lower bioactivity compared with their parent compound. To solve this problem, we designed and synthesised a series of ester-capped amino-acid-conjugated chlorantraniliproles.

Uptake and phloem transport of glucose-fipronil conjugate in Ricinus communis involve a carrier-mediated mechanism.

Some compounds containing glucose are absorbed via the monosaccharide transporters of the plasma membrane. A glucose-fipronil conjugate, N-[3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazol-5-yl]-1-(β-d-glucopyranosyl)-1H-1,2,3-triazole-4-methanamine (GTF), has been synthesized in our previous work. GTF exhibits moderate phloem mobility in Ricinus communis.