Saflufenacil

Uses

Saflufenacil-d7 is the labeled version of Saflufenacil (S081800), which is a herbicide of the pyrimidinedione chemical class used for the preplant burndown and selective preemergence dicot weed control in different field crops. It was found to inhibit protoporphyrinogen IX oxidase (PPO) enzyme.

Definition

ChEBI: Saflufenacil is a member of the class of sulfamides that is sulfamide in which one of the amino groups has been substituted by a methyl group an an isopropyl group, while the other has been substituted by a 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]benzoyl group. An important BASF herbicide, not registered in Europe but sold in USA, Canada and several other countries to control weeds in a wide range of food crops. Often mixed with other products such as glyphosate. It has a role as an EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor, a herbicide and an agrochemical. It is a member of monochlorobenzenes, a member of monofluorobenzenes and a member of sulfamides. It is functionally related to a uracil.

Synthesis

A preparation method of saflufenacil is characterized by comprising the following steps:
(1) adding an I-methyl intermediate and a solvent into an organic solvent, and carrying out continuous chlorination reaction under pressure to obtain an intermediate I-trichlorobenzyl;
(2) adding I-trichlorobenzyl and a sulfuryl diamide intermediate into an organic solvent for condensation reaction to obtain a product saflufenacil;
the reaction formula is as follows:

Mode of action

Physiological and biochemical profiling confirmed that saflufenacil was a protoporphyrinogen-IX-oxidase (PPO) inhibitor. Saflufenacil elicits symptoms similar to other peroxidizing herbicides, including rapid, light-dependent necrosis of foliar tissue. Saflufenacil is readily absorbed by the root and shoot tissue of plants. Once absorbed, Saflufenacil is predominantly translocated via the xylem, with limited movement via the phloem. Saflufenacil is highly effective in controlling dicot weeds through contact and residual activity. In addition to non-crop and pre-plant burndown utility, saflufenacil demonstrates preemergence selectivity in a wide range of crops. Selectivity is conferred by physical placement and rapid metabolism of saflufenacil in tolerant crop species such as corn.