Protoporphyrinogen oxidase inhibitors
AssigneeEnko Chem, Inc.
InventorsNeville John Anthony, Paul Galatsis, David Jeffrey Lauffer, Peter Stchur, III
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Abstract
The present invention relates to protoporphyrinogen IX oxidase (PPO) inhibitors of the general formula (I) where the variables are defined herein. The invention features processes and intermediates for preparing the compounds of formula (I), compositions comprising them, and their use as herbicides—e.g., for controlling harmful plants. The invention also features methods for controlling unwanted vegetation comprising allowing an herbicidal effective amount of at least one PPO inhibitor of formula (I) to act on plants, their seed, and/or their habitat.
Claims37
A compound of formula (I):
- or suitable salt thereof, wherein:
- X is —CH or —N;
- R1 is —SR1a or —S(O)2R1b;
- R1a is C1-4alkyl optionally substituted with phenyl, C(O)OR1c, or C(O)N(R1c)2;
- each R1c is independently, H, CH2CH2OC(O)R1d, or optionally substituted C1-4alkyl, wherein the optional substituents are C3-6cycloalkyl, C(O)OC1-4alkyl, or up to 3 F atoms, or two R1c with an intervening nitrogen atom form a 5-6 membered ring optionally substituted with C(O)OH or C(O)OC1-4alkyl;
- R1d is C1-4alkyl or C1-4alkenyl;
- R1b is CH2C(O)C1-4alkyl or N(R1e)R1f;
- R1e is H, C1-4alkyl, C1-4alkenyl, C1-4alkynyl, C(O)C1-2alkyl, or OC1-4alkyl;
- R1f is H, C1-6alkyl, C(O)C(O)C1-4alkyl, C(O)R1g, or S(O)2R1g, or R1e and R1f together with the intervening nitrogen atom form a 5-6 membered ring, optionally containing up to two C(O) ring members;
- R1g is C1-4alkyl, C1-4alkenyl, phenyl, Het, N(Rh)2, OC1-4alkyl, C3-6cycloalkyl, or CH2(OCH2CH2)4CH3, wherein each alkyl group is optionally substituted with up to 3 F atoms, phenyl, C3-6cycloalkyl, OH, OC1-4alkyl, wherein each cycloalkyl group is optionally substituted with OH or OC1-4alkyl, wherein each phenyl is optionally substituted with up to 3 Cl or F atoms, and wherein Het is a 5-6 membered heterocyclic ring containing up to two ring members selected from O, N, S, or S(O)2 and optionally substituted with OH or OC1-4alkyl;
- each Rh is, independently H, C1-4alkyl, benzyl, or phenyl;
- each of R2 and R3 is Cl or F;
- and
- each of R4, R5, and R6 is F or H, wherein Ring A comprises at least 4 F atoms.
A compound selected from the group consisting of:
- or a salt thereof.
Dependencies are inferred from the claim text.