2,6-dihalo-5-alkoxy-4-substituted-pyrimidines, pyrimidine- carbaldehydes, and methods of formation and use
AssigneeDow AgroSciences LLC
InventorsThomas Lyman Siddall, Joshua John Roth
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Abstract
2,6-Dihalo-5-alkoxy-4-substituted-pyrimidines, 2,6-dihalo-5-alkoxy-4-pyrimdine carbaldehydes, and derivatives of each are useful intermediates in forming potent herbicides that demonstrate a broad spectrum of weed control. These compounds are disclosed, as are methods of forming and using these compounds.
Claims23
A compound of the formula I
- wherein
- X1 represents a halogen;
- R1 represents a hydrocarbon chain;
- and
- Q represents a C1-C2 alkoxy.
A compound of the formula II
- wherein
- X1 represents a halogen;
- and
- Q represents a C1-C2 alkoxy.
A method of farming a 2,6-dihalo-5-alkoxy-pyrimdine-4-carbaldehyde comprising reacting a 2,6-dihalo-5-alkoxy-4-substituted pyrimidine with an oxidant.
A method of forming a 2,6-dihalo-5-alkoxy-4-substituted pyrimidine comprising:
- reacting a 2,6-dihalo-5-alkoxy pyrimidine with an organometallic halide reagent to form a 2,6-dihalo-5-alkoxy-4-substituted-3-(metal-halo or metal) pyrimidine;
- and
- oxidizing the 2,6-dihalo-5-alkoxy-4-substituted-3-(metal-halo or metal) pyrimidine to form the 2,6-dihalo-5-alkoxy-4-substituted pyrimidine.
A method of using a 2,6-dihalo-5-alkoxy-4-substituted pyrimidine to form an herbicide, the 2,6-dihalo-5-alkoxy-4-substituted pyrimidine comprising a pyrimidine ring having a 4 position and a 6 position, the pyrimidine ring further comprising a hydrocarbon chain at the 4 position and a halogen at the 6 position, the method comprising:
- contacting the hydrocarbon chain at the 4 position with an oxidant to form a carbonyl group at the 4 position;
- contacting the carbonyl group at the 4 position with bromine in an alcohol to form a carboalkoxy group at the 4 position;
- and
- contacting the halogen at the 6 position with an amine to form an amino group at the 6 position.
A method of using 2,6-dihalo-5-alkoxy-4-substituted pyrimidine to form a 2,6-dihalo-5-alkoxy-pyrimidine-4-carboxylic acid, the 2,6 dihalo-5-alkoxy-4-substituted pyrimidine comprising a pyrimidine ring comprising a 4 position, the pyrimidine ring comprising a hydrocarbon chain at the 4 position, the method comprising contacting the hydrocarbon chain at the 4 position with an oxidant to form a carboxyl group at the 4 position.
Dependencies are inferred from the claim text.