Granted Patent B2

US 12,637,438 · App. 18/234,250 · Granted May 26, 2026

Inventors: Neville John Anthony (Northborough, MA); Paul Galatsis (Newton, MA); David Jeffrey Lauffer (Stow, MA); Peter Stchur, III (Waterford, CT)

Assignee: Enko Chem, Inc.

C07D265/38A01N43/84A01P13/02

Abstract

Claims (87)

1 . 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:

R 1 is H or C 1-4 alkyl optionally substituted with R 1a , 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 OC 1-4 alkyl group;

R 1a is

each R 1b is, independently, H, C 1-4 alkyl, or cyclopropyl;

each of R 2 and R 3 is, independently, H, Cl, F, CH 3 , or R 2 and R 3 together with the intervening carbon is cyclopropyl;

R 4 is H, Cl, or F;

R 5 is H or F;

each of R 6 and R 7 is, independently, F, H, C 1-2 alkyl optionally substituted with OH, alkenyl, OH, OC 1-2 alkyl, O-cyclopropyl, OCH 2 CCH, NHCH 2 Ph, N(R x ) 2 , or SCH 3 ;

R 8 is H or F;

each R x is, independently, H, CH 3 , or C(O)CH 3 ; and

wherein Ring A contains at least 4 F atom substituents.

2 . The method of claim 1 , wherein the compound is of formula II:

or a salt thereof, wherein R 1 , R 2 , R 3 , and R 4 are as defined in formula I.

3 . The method of claim 1 , wherein the compound is of formula III:

or a salt thereof, wherein R 1 , R 2 , R 3 , and R 4 are as defined in formula I.

4 . The method of claim 1 , wherein the compound is of formula IV:

or a salt thereof, wherein R 1 , R 2 , R 3 , and R 4 are as defined in formula I.

5 . The method of claim 1 , wherein each of R 2 , R 3 , and R 4 is F.

6 . The method of claim 1 , wherein each of R 2 and R 3 is H and R 4 is F.

7 . The method of claim 1 , wherein each of R 2 , R 3 , and R 4 is F, and R 1 is CH 2 CCH.

8 . The method of claim 1 , wherein the composition further comprises at least one additional component that serves as a carrier.

9 . The method of claim 8 , wherein the at least one additional component in the composition is a surfactant or a diluent.

10 . The method of claim 1 , wherein the composition is an herbicidal composition.

11 . The method of claim 1 , wherein the PPO inhibitor-resistant weeds have a dG210 mutation.

12 . The method of claim 1 , wherein the composition is applied at a rate of 1 to 100 g per 10,000 m 2 .

13 . The method of claim 1 , wherein the contacting the undesired vegetation or its environment with the composition leads to postemergence control of the undesired vegetation.

14 . The method of claim 1 , wherein the undesired vegetation is at least 60% controlled.

15 . The method of claim 1 , wherein the undesired vegetation is controlled in a field of corn, soybean, wheat and/or cotton.

16 . The method of claim 1 , wherein the contacting the undesired vegetation or its environment with the composition leads to preemergence control of the undesired vegetation.

17 . 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.

18 . The method of claim 17 , wherein the compound is:

or a salt thereof.

19 . A method of preparing a compound of formula (I):

or a salt thereof, wherein:

R 1 is H or C 1-4 alkyl optionally substituted with R 1a , 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 OC 1-4 alkyl group;

R 1a is

each R 1b is, independently, H, C 1-4 alkyl, or cyclopropyl;

each of R 2 and R 3 is, independently, H, Cl, F, CH 3 , or R 2 and R 3 together with the intervening carbon is cyclopropyl;

R 4 is H, Cl, or F;

R 5 is H or F;

each of R 6 and R 7 is, independently, F, H, C 1-2 alkyl optionally substituted with OH, alkenyl, OH, OC 1-2 alkyl, O-cyclopropyl, OCH 2 CCH, NHCH 2 Ph, N(R x ) 2 , or SCH 3 ;

R 8 is H or F;

each R x is, independently, H, CH 3 , or C(O)CH 3 ; 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 R 1 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

R 1 -R 8 and ring A are as defined for formula (I).

20 . A method of preparing a compound of formula (I):

or a salt thereof, wherein:

R 1 is H or C 1-4 alkyl optionally substituted with R 1a , 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 OC 1-4 alkyl group;

R 1a is

each R 1b is, independently, H, C 1-4 alkyl, or cyclopropyl;

each of R 2 and R 3 is, independently, H, Cl, F, CH 3 , or R 2 and R 3 together with the intervening carbon is cyclopropyl;

R 4 is H, Cl, or F;

R 5 is H or F;

each of R 6 and R 7 is, independently, F, H, C 1-2 alkyl optionally substituted with OH, alkenyl, OH, OC 1-2 alkyl, O-cyclopropyl, OCH 2 CCH, NHCH 2 Ph, N(R x ) 2 , or SCH 3 ;

R 8 is H or F;

each R x is, independently, H, CH 3 , or C(O)CH 3 ; 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

R 1 -R 8 and ring A are as defined for formula (I).

21 . A compound of formula (c), (d), (e), (g), or (h):

or a salt thereof, wherein:

each of R 2 and R 3 is, independently, H, Cl, F, CH 3 , or R 2 and R 3 together with the intervening carbon is cyclopropyl;

R 4 is H, Cl, or F;

R 5 is H or F;

each of R 6 and R 7 is, independently, F, H, C 1-2 alkyl optionally substituted with OH, alkenyl, OH, OC 1-2 alkyl, O-cyclopropyl, OCH 2 CCH, NHCH 2 Ph, N(R x ) 2 , or SCH 3 ;

R 8 is H or F;

each R x is, independently, H, CH 3 , or C(O)CH 3 ; and

wherein Ring A contains at least 4 F atom substituents,

wherein the compound is not

22 . The compound of claim 21 , wherein the compound is of formula (d), (e), (g), or (h):

or a salt thereof.

Assignments (1)

Continuity (6)

References Cited (300)