- Synthesis of 6-Aryl-5-fluoropicolinate Herbicides via Halex Reaction of Tetrachloropicolinonitrile
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The development of a new synthesis of 6-aryl-5-fluoropicolinate herbicides is described. This general route employs the halogen exchange (halex) reaction of tetrachloropicolinonitrile to give a mixture of chlorofluoropicolinonitriles. It was found that th
- Whiteker, Gregory T.,Froese, Robert D. J.,Arndt, Kim E.,Renga, James M.,Zhu, Yuanming,Roth, Gary A.,Yang, Qiang,Canturk, Belgin,Klosin, Jerzy
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p. 2166 - 2174
(2019/08/26)
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- The discovery of Arylex active and Rinskor active: Two novel auxin herbicides
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Multiple classes of commercially important auxin herbicides have been discovered since the 1940s including the aryloxyacetates (2,4-D, MCPA, dichlorprop, mecoprop, triclopyr, and fluroxypyr), the benzoates (dicamba), the quinoline-2-carboxylates (quinclorac and quinmerac), the pyrimidine-4-carboxylates (aminocyclopyrachlor), and the pyridine-2-carboxylates (picloram, clopyralid, and aminopyralid) In the last 10 years, two novel pyridine-2-carboxylate (or picolinate) herbicides were discovered at Dow AgroSciences This paper will describe the structure activity relationship study that led to the discovery of the 6-aryl-picolinate herbicides Arylex active (2005) and Rinskor active (2010) While Arylex was developed primarily for use in cereal crops and Rinskor is still in development primarily for use in rice crops, both herbicides will also be utilized in additional crops.
- Epp, Jeffrey B.,Alexander, Anita L.,Balko, Terry W.,Buysse, Ann M.,Brewster, William K.,Bryan, Kristy,Daeuble, John F.,Fields, Stephen C.,Gast, Roger E.,Green, Renard A.,Irvine, Nicholas M.,Lo, William C.,Lowe, Christian T.,Renga, James M.,Richburg, John S.,Ruiz, James M.,Satchivi, Norbert M.,Schmitzer, Paul R.,Siddall, Thomas L.,Webster, Jeffery D.,Weimer, Monte R.,Whiteker, Gregory T.,Yerkes, Carla N.
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p. 362 - 371
(2016/01/25)
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- Synthesis of Novel Fluoropicolinate Herbicides by Cascade Cyclization of Fluoroalkyl Alkynylimines
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The cascade cyclization of fluoroalkyl alkynylimines with primary amines has been modified to allow the synthesis of 4-amino-5-fluoropicolinates. Use of N-trityl and acetal protecting groups in the cyclization precursor led to 5-fluoropyridines that were
- Johnson, Peter L.,Renga, James M.,Galliford, Christopher V.,Whiteker, Gregory T.,Giampietro, Natalie C.
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supporting information
p. 2905 - 2907
(2015/06/30)
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- PROCESS FOR THE PREPARATION OF 4-AMINO-5-FLUORO-3-CHLORO-6-(SUBSTITUTED)PICOLINATES
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4-Amino-5-fluoro-3-chloro-6-(substituted)picolinates are prepared from trifluoroacetic acid, p-methoxyaniline, a C1-C4 alkyl propiolate and a substituted methylene amine by a series of steps.
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Paragraph 0053; 0054
(2014/06/25)
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- 6-Aryl-4-aminopicolinates and their use as herbicides
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4-Aminopicolinic acids having aryl or heteroaryl substituents in the 6-position and their amine and acid derivatives are potent herbicides demonstrating a broad spectrum of weed control.
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