Protoporphyrinogen oxidase inhibitors
AssigneeEnko Chem, Inc.
InventorsNeville John Anthony, Paul Galatsis, David Jeffrey Lauffer, Peter Stchur, III
Life of this patent
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Abstract
The present invention relates to protoporphyrinogen oxidase inhibitors of the general formula (I) where the variables are defined herein. The invention features processes and intermediates for preparing the benzoxazinones of formula (I), compositions comprising them, and their use as herbicides—i.e. for controlling harmful plants. The invention also features methods for controlling unwanted vegetation comprising allowing an herbicidal effective amount of at least one benzoxazinone of formula (I) to act on plants, their seed, and/or their habitat.
Claims22
A method of controlling undesired vegetation, wherein the undesired vegetation comprises protoporphyrinogen IX oxidase (PPO) inhibitor-resistant weeds, the method comprising contacting the undesired vegetation or its environment with an herbicidally effective amount of a composition comprising a compound of formula I:
- or a salt thereof, wherein:
- R1 is H or C1-4alkyl optionally substituted with R1a, phenyl, or benzyl, wherein each of said alkyl, phenyl or benzyl is optionally substituted with up to 3 F atoms, an OH group, or an OC1-4alkyl group;
- R1a is
- each R1b is, independently, H, C1-4alkyl, or cyclopropyl;
- each of R2 and R3 is, independently, H, Cl, F, CH3, or R2 and R3 together with the intervening carbon is cyclopropyl;
- R4 is H, Cl, or F;
- R5 is H or F;
- each of R6 and R7 is, independently, F, H, C1-2alkyl optionally substituted with OH, alkenyl, OH, OC1-2alkyl, O-cyclopropyl, OCH2CCH, NHCH2Ph, N(Rx)2, or SCH3;
- R8 is H or F;
- each Rx is, independently, H, CH3, or C(O)CH3;
- and
- wherein Ring A contains at least 4 F atom substituents.
A method of controlling undesired vegetation, wherein the undesired vegetation comprises protoporphyrinogen IX oxidase (PPO) inhibitor-resistant weeds, the method comprising contacting the undesired vegetation or its environment with an herbicidally effective amount of a compound selected from the group consisting of
- or a salt thereof.
A method of preparing a compound of formula (I):
- or a salt thereof, wherein:
- R1 is H or C1-4alkyl optionally substituted with R1a, phenyl, or benzyl, wherein each of said alkyl, phenyl or benzyl is optionally substituted with up to 3 F atoms, an OH group, or an OC1-4alkyl group;
- R1a is
- each R1b is, independently, H, C1-4alkyl, or cyclopropyl;
- each of R2 and R3 is, independently, H, Cl, F, CH3, or R2 and R3 together with the intervening carbon is cyclopropyl;
- R4 is H, Cl, or F;
- R5 is H or F;
- each of R6 and R7 is, independently, F, H, C1-2alkyl optionally substituted with OH, alkenyl, OH, OC1-2alkyl, O-cyclopropyl, OCH2CCH, NHCH2Ph, N(Rx)2, or SCH3;
- R8 is H or F;
- each Rx is, independently, H, CH3, or C(O)CH3;
- and
- wherein Ring A contains at least 4 F atom substituents,
- the method comprising:
- i) deprotecting a compound of formula (c), or a salt thereof, to yield a compound of formula (d), or a salt thereof,
- ii) reducing the compound of formula (d), or a salt thereof, to yield a compound of formula (e), or a salt thereof,
- iii) reacting the compound of formula (e), or a salt thereof, with a compound of formula (f), or a salt thereof, to yield a compound of formula (g), or a salt thereof,
- iv) cyclizing the compound of formula (g), or a salt thereof, to yield a compound of formula (h), or a salt thereof,
- and
- when R1 is other than H, the method further comprises:
- v) reacting the compound of formula (h), or a salt thereof, with a compound of formula (i), or a salt thereof, to yield the compound of formula (I), or a salt thereof,
- wherein:
- Y is X or B (OH) 2;
- X is Br or I;
- and
- R1-R8 and ring A are as defined for formula (I).
A method of preparing a compound of formula (I):
- or a salt thereof, wherein:
- R1 is H or C1-4alkyl optionally substituted with R1a, phenyl, or benzyl, wherein each of said alkyl, phenyl or benzyl is optionally substituted with up to 3 F atoms, an OH group, or an OC1-4alkyl group;
- R1a is
- each R1b is, independently, H, C1-4alkyl, or cyclopropyl;
- each of R2 and R3 is, independently, H, Cl, F, CH3, or R2 and R3 together with the intervening carbon is cyclopropyl;
- R4 is H, Cl, or F;
- R5 is H or F;
- each of R6 and R7 is, independently, F, H, C1-2alkyl optionally substituted with OH, alkenyl, OH, OC1-2alkyl, O-cyclopropyl, OCH2CCH, NHCH2Ph, N(Rx)2, or SCH3;
- R8 is H or F;
- each Rx is, independently, H, CH3, or C(O)CH3;
- and
- wherein Ring A contains at least 4 F atom substituents,
- the method comprising reacting a compound of formula (n), or a salt thereof, with a compound of formula (o), or a salt thereof, to form the compound of formula (I), or a salt thereof,
- wherein:
- R is H or phenyl;
- X is Br or I;
- and
- R1-R8 and ring A are as defined for formula (I).
A compound of formula (c), (d), (e), (g), or (h):
- or a salt thereof, wherein:
- each of R2 and R3 is, independently, H, Cl, F, CH3, or R2 and R3 together with the intervening carbon is cyclopropyl;
- R4 is H, Cl, or F;
- R5 is H or F;
- each of R6 and R7 is, independently, F, H, C1-2alkyl optionally substituted with OH, alkenyl, OH, OC1-2alkyl, O-cyclopropyl, OCH2CCH, NHCH2Ph, N(Rx)2, or SCH3;
- R8 is H or F;
- each Rx is, independently, H, CH3, or C(O)CH3;
- and
- wherein Ring A contains at least 4 F atom substituents,
- wherein the compound is not
Dependencies are inferred from the claim text.