Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume -, Issue -, Pages -Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jafc.3c01634
Keywords
aryl pyrrolidinoneanilide; grass weed control; pyrimidine biosynthesis; dihydroorotate dehydrogenase
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This paper describes the discovery and optimization process of a new herbicide with excellent weed control and safety on rice. It also introduces the proposed common name and the classification of this herbicide.
Thelast new herbicidal modes-of-action with commercialsignificancewere introduced to the marketplace multiple decades ago. Serious weedresistance to most herbicidal classes have since emerged with widespreaduse. Aryl pyrrolidinone anilides represent an entirely new mode-of-actionclass of herbicides that interfere with de novo pyrimidinebiosynthesis in plants via inhibition of dihydroorotate dehydrogenase.The chemical lead for this new herbicide class discovery was identifiedfrom high-volume sourced greenhouse screening that required structuralreassignment of the hit molecule followed by an extensive syntheticoptimization effort. With excellent grass weed control and pronouncedsafety on rice, the selected commercial development candidate hasa proposed common name of tetflupyrolimet and represents the firstmember of the new HRAC (Herbicide Resistance Action Committee) Group28. This paper describes the discovery path to tetflupyrolimet withan added focus on the bioisosteric modifications pursued in optimization,including replacements of the lactam core itself.
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