Methionine Biosynthesis‐Inhibiting Anilinopyrimidine Fungicides

Lamberth, Clemens

doi:10.1002/9783527664412.ch12

Cited by 8 publications

(11 citation statements)

References 23 publications

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“…The anilinopyrimidine fungicide mepanipyrim 115 (Frupica, Cockpit, Figure ), introduced by Kumiai Chemical Industry in 1995, is widely used as a methionine biosynthesis inhibitor. − It is used to control a wide range of fungal pathogens, such as Botrytis cinerea (gray mold) on vines and vegetables, Venturia sp. (scab) on apples and pears, and Monilinia fructicola (brown rot) on peaches.…”

Section: Carbon–nitrogen Bond Forming Cross-couplingsmentioning

confidence: 99%

Palladium-Catalyzed Cross-Coupling Reactions: A Powerful Tool for the Synthesis of Agrochemicals

Devendar

Kang

et al. 2018

J. Agric. Food Chem.

316

165

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Pd-catalyzed cross-coupling reactions have become essential tools for the construction of carbon-carbon and carbon-heteroatom bonds. Over the last three decades, great efforts have been made with cross-coupling chemistry in the discovery, development, and commercialization of innovative new pharmaceuticals and agrochemicals (mainly herbicides, fungicides, and insecticides). In view of the growing interest in both modern crop protection and cross-coupling chemistry, this review gives a comprehensive overview of the successful applications of various Pd-catalyzed cross-coupling methodologies, which have been implemented as key steps in the synthesis of agrochemicals (on R&D and pilot-plant scales) such as the Heck, Suzuki, Sonogashira, Stille, and Negishi reactions, as well as decarboxylative, carbonylative, α-arylative, and carbon-nitrogen bond bond-forming cross-coupling reactions. Some perspectives and challenges for these catalytic coupling processes in the discovery of agrochemicals are briefly discussed in the final section. The examples chosen demonstrate that cross-coupling chemistry approaches open-up new, low-cost, and more efficient industrial routes to existing agrochemicals, and such methods also have the capability to lead the new generation of pesticides with novel modes of action for sustainable crop protection.

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Section: Carbon–nitrogen Bond Forming Cross-couplingsmentioning

confidence: 99%

Palladium-Catalyzed Cross-Coupling Reactions: A Powerful Tool for the Synthesis of Agrochemicals

Devendar

Kang

et al. 2018

J. Agric. Food Chem.

316

165

View full text Add to dashboard Cite

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“…Although ferimzone ( 37 ) is a closely related, stretched version of pyrimethanil ( 36 ), the two fungicides do not share the same mode of action. Pyrimethanil ( 36 ) belongs to the methionine biosynthesis inhibiting anilinopyrimidines, whereas the elongated ferimzone ( 37 ) has an unknown mode of action. , The cellulose synthase inhibitor 39 is a derivative of mandipropamid ( 38 ) elongated by an additional two-atom spacer. Both compounds 38 and 39 have been shown to possess high potency against the oomycete pathogens Plasmopara viticola and Phytophthora infestans (Scheme ).…”

Section: Further Insertion Examples Involving Other Mode Of Action Cl...mentioning

confidence: 99%

Insertion of Small Flexible Linkers as a Useful Scaffold Hopping Tool in Agrochemistry

Lamberth

2022

J. Agric. Food Chem.

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Inserting small flexible linkers of only one- to three-atom chain lengths into a molecular backbone is an important scaffold hopping manipulation. Analogues derived from biologically active compounds through the utilization of such a strategy are often similar in shape and physicochemical properties and, therefore, likely to exhibit similar potency. This review will demonstrate how the elongation with oxygen, amino, methylene, ethylene, vinyl, ethynyl, and CH2O bridges led to the discovery of highly active agrochemicals.

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“…Cyprodinil belongs to the methionine biosynthesis inhibiting anilinopyrimidine fungicides and shows potent efficacy against different Ascomycetes pathogens, such as Botrytis cinerea , causal agent of gray mold, and Alternaria solani , causal agent of early blight (Scheme 3). 21,22 …”

Section: Fungicides Originating From Herbicide Leadsmentioning

confidence: 99%

“…Scheme 4. Fungicides metalaxyl(15), diclocymet(18) and proquinazid(21) and their roots in herbicide chemistry.…”

mentioning

confidence: 99%

The power of cross‐indication testing: agrochemicals originally stemming from a different indication

Lamberth

2022

Pest Management Science

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Cross‐indication testing is the assaying of final compounds, but also their intermediates or side products, from one agrochemical indication against target species of other product lines. This approach has proven to be a highly successful source of lead compounds, which led to several important crop protection products. This review article describes, which herbicides came from fungicides and insecticides, how fungicides have been obtained from herbicide and insecticide leads and which insecticides have their roots in herbicide and fungicide chemistry. © 2022 Society of Chemical Industry.

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Methionine Biosynthesis‐Inhibiting Anilinopyrimidine Fungicides

Cited by 8 publications

References 23 publications

Palladium-Catalyzed Cross-Coupling Reactions: A Powerful Tool for the Synthesis of Agrochemicals

Palladium-Catalyzed Cross-Coupling Reactions: A Powerful Tool for the Synthesis of Agrochemicals

Insertion of Small Flexible Linkers as a Useful Scaffold Hopping Tool in Agrochemistry

The power of cross‐indication testing: agrochemicals originally stemming from a different indication

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