Alkyl sulfones: discovery of novel structural types with differentiated opportunities for insect control.

The discovery of novel chemical classes with novel modes of action for insect control form the backbone of innovation with the goal to deliver much-needed solutions into the hands of growers. Over the last decade, alkyl sulfones have emerged as one of the most versatile new classes and are under intensive investigation in many R&D programs in the industry, with Sumitomo Chemicals recently introducing oxazosulfyl as a first active ingredient to the market. In this review, we discuss some of our strategies to invent novel classes based upon ligand-based design, and also show how incorporation of physical chemical properties into our design enabled us to predictably control chewing and sucking pests.

The Discovery of Bicyclopyrone.

Two short topics were presented in the lecture titled Some Highlights of an Agro Career presented at the Fall Meeting Swiss Chemical Society, September 10th, 2021. The first of these topics discussed the discovery of the selective corn herbicide Bicyclopyrone. The second topic presented was concerned with host marking pheromones (HMPs), and described the HMP of the Mexican fruit fly anastrepha ludens, and its use in crop protection.

Synthetic approaches to the 2015-2018 new agrochemicals.

In this review, the synthesis of 33 agrochemicals that received an international standardization organization (ISO) name between January 2015 and December 2018 is described. The aim is to showcase the broad range and scope of reactions, reagents and intermediates used to discover and produce the latest active ingredients addressing the crop protection industry's needs.

Synthetic approaches to the 2010-2014 new agrochemicals.

In this review, the synthesis of 30 agrochemicals that received an international standardization organization (ISO) name during the last five years (January 2010 to December 2014) is described. The aim is to showcase the range and scope of chemistries used to discover or produce the latest active ingredients addressing the crop protection industry's needs.

Bicyclic heterocyclic anthranilic diamides as ryanodine receptor modulators with insecticidal activity.

The diamide insecticides act on the ryanodine receptor (RyR). The synthesis of various bicyclic anthranilic derivatives is reported. Their activity against the insect ryanodine receptor (RyR) and their insecticidal activity in the greenhouse is presented, as well as structure activity relationship considerations.

Efficient synthesis of fused bicyclic ethers and their application in herbicide chemistry.

A series of triketones 2 and 3 featuring novel fused bicyclic aryl ethers have been prepared. The syntheses utilized ring-closing olefin metathesis (compounds 2), or oxidative cyclization of allylphenols as the key steps. The herbicidal activity of the targeted triketones 2 and 3 on various grasses and broad-leaved weeds was determined and compared with compound 1.

A Robust Protocol for Pd(II)-catalyzed C-3 Arylation of () Indazoles and Pyrazoles: Total Synthesis of Nigellidine Hydrobromide.

C3-arylated indazole and pyrazoles are privileged structural motifs in agrochemicals and pharmaceuticals. C-3 C-H arylation of () indazole and pyrazole has been a significant challenge due to the poor reactivity of the C-3 position. Herein, we report a practical Pd(II)/Phen catalyst and conditions for direct C-3 arylation of indazole and pyrazole with ArI or ArBr without using Ag additives as halide scavengers.

Investigating the mode of action of sulfoxaflor: a fourth-generation neonicotinoid.

Background: The precise mode of action of sulfoxaflor, a new nicotinic acetylcholine receptor-modulating insecticide, is unclear. A detailed understanding of the mode of action, especially in relation to the neonicotinoids, is essential for recommending effective pest management practices.

Results: Radiolabel binding experiments using a tritiated analogue of sulfoxaflor ([(3) H]-methyl-SFX) performed on membranes from Myzus persicae demonstrate that sulfoxaflor interacts specifically with the high-affinity imidacloprid binding site present in a subpopulation of the total nAChR pool.

Ligand-promoted C3-selective arylation of pyridines with Pd catalysts: gram-scale synthesis of (±)-preclamol.

The first example of Pd-catalyzed, C3-selective arylation of unprotected pyridines has been developed by employing a catalytic system consisting of Pd(OAc)(2) and 1,10-phenanthroline. This protocol provides an expeditious route to an important class of 3-arylpyridines and 3-arylpiperidines frequently found in bioactive compounds. A brief synthesis of the drug molecule (±)-preclamol is also reported.

Synthesis of CF3-substituted sulfoximines from sulfonimidoyl fluorides.

N-Protected trifluoromethyl-substituted sulfoximines have been prepared by treatment of sulfonimidoyl fluorides with a combination of the Ruppert-Prakash reagent (TMSCF(3)) and tetrabutyl ammonium fluoride (TBAF). The starting materials were accessed following two synthetic routes, and for each reaction sequence the substrate scope was evaluated. Accordingly, a wide variety of aryl-substituted products were obtained in moderate to good yield.

Host marking pheromone (HMP) in the Mexican fruit fly Anastrepha ludens.

Host marking pheromones (HMPs) are used by insects to mark hosts (usually a fruit) where they have already laid eggs. The compounds serve as a deterrent to conspecifics avoiding over-infestation of hosts (i.e.

Herbicidal 4-hydroxyphenylpyruvate dioxygenase inhibitors--a review of the triketone chemistry story from a Syngenta perspective.

A review, outlining the origins and subsequent development of the triketone class of herbicidal 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors.