US 5,723,411 AGranted

Herbicidal pyridazinones

AssigneeE. I. Du Pont de Nemours and Company

InventorThomas Martin Stevenson

Life of this patent

Estimating the term…

Abstract

Compounds of Formula I, and their N-oxides and agriculturally-suitable salts, are disclosed which are useful for controlling undesired vegetation ##STR1## wherein Q, W, R.sup.1, R.sup.2 and R.sup.3 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula I and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective mount of a compound of Formula I.

Claims4

Dependent claims

A compound selected from Formula I, N-oxides and agriculturally-suitable salts thereof, ##STR25## wherein:

Q is phenyl, substituted with R.sup.4 and optionally substituted with up to three R.sup.5 ;
provided that, when R.sup.4 and an adjacently attached R.sup.5 are taken together, then Q is selected from the group ##STR26## A is --CH.sub.2 -- or --CH.sub.2 --CH.sub.2 --, each group optionally substituted with 1-4 halogen;
W is O or S;
R.sup.1 is H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, or C.sub.3 -C.sub.6 cycloalkyl;
R.sup.2 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy, halogen, or cyano;
R.sup.3 is OR.sup.6, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 haloalkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 haloalkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, C.sub.1 -C.sub.6 haloalkylsulfonyl, mercapto, or halogen;
R.sup.4 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, OR.sup.7, S(O).sub.m R.sup.8, S(O).sub.2 NR.sup.9 R.sup.10, C(.dbd.O)R.sup.8, C(.dbd.O)OR.sup.8, C(.dbd.O)NR.sup.9 R.sup.10, NR.sup.11 R.sup.12, halogen, cyano, or nitro;
each R.sup.5 is independently C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, OR.sup.7, S(O).sub.m R.sup.8, S(O).sub.2 NR.sup.9 R.sup.10, C(.dbd.O)R.sup.8, C(.dbd.O)OR.sup.8, C(.dbd.O)NR.sup.9 R.sup.10, NR.sup.11 R.sup.12, halogen, cyano, or nitro;
or
R.sup.6 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkoxyalkyl, formyl, C.sub.2 -C.sub.6 alkylcarbonyl, C.sub.2 -C.sub.6 alkoxycarbonyl, C.sub.2 -C.sub.6 alkylamino carbonyl, C.sub.3 -C.sub.7 dialkylaminocarbonyl, C.sub.1 -C.sub.6 alkylsulfonyl, or C.sub.1 -C.sub.6 haloalkylsulfonyl;
or R.sup.6 is benzoyl or phenylsulfonyl, each optionally substituted with C.sub.1 -C.sub.3 alkyl, halogen, cyano, or nitro;
each R.sup.7 is independently C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.4 -C.sub.6 cycloalkylalkyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.5 cyanoalkyl, formyl, C.sub.2 -C.sub.5 alkylcarbonyl, C.sub.2 -C.sub.5 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylsulfonyl, or C.sub.1 -C.sub.4 haloalkylsulfonyl;
each R.sup.8 is independently C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.4 -C.sub.6 cycloalkylalkyl, C.sub.2 -C.sub.6 alkoxyalkyl, or C.sub.2 -C.sub.5 cyanoalkyl;
each R.sup.9 is independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, or C.sub.1 -C.sub.6 alkoxy;
or R.sup.9 is phenyl or benzyl, each optionally substituted on the phenyl ring with C.sub.1 -C.sub.3 alkyl, halogen, cyano, or nitro;
each R.sup.10 is independently H, C.sub. -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, or C.sub.3 -C.sub.6 haloalkynyl;
or
each pair of R.sup.9 and R.sup.10, when attached to the same atom, can independently be taken together as --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --, each group optionally substituted with 1-2 C.sub.1 -C.sub.3 alkyl;
each R.sup.11 is independently H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.4 -C.sub.6 cycloalkylalkyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.5 cyanoalkyl, formyl, C.sub.2 -C.sub.5 alkylcarbonyl, C.sub.2 -C.sub.5 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylsulfonyl, or C.sub.1 -C.sub.4 haloalkylsulfonyl;
each R.sup.12 is independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, or C.sub.1 -C.sub.6 alkoxy;
or R.sup.12 is phenyl or benzyl, each optionally substituted on the phenyl ring with C.sub.1 -C.sub.3 alkyl, halogen, cyano, or nitro;
or
each pair of R.sup.11 and R.sup.12, when attached to the same atom, can independently be taken together as --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --, each group optionally substituted with 1-2 C.sub.1 -C.sub.3 alkyl;
R.sup.13 is H or C.sub.1 -C.sub.4 alkyl;
each R.sup.14 is independently C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 haloalkylthio, hydroxy, or halogen;
or two R.sup.14 bonded to the same carbon atom can be taken together as --OCH.sub.2 CH.sub.2 O--, --OCH.sub.2 CH.sub.2 CH.sub.2 O--, --SCH.sub.2 CH.sub.2 S--, or --SCH.sub.2 CH.sub.2 CH.sub.2 S--, each CH.sub.2 optionally substituted with 1-2 CH.sub.3 or 1-2 halogen;
or two R.sup.14 bonded to the same carbon atom can be taken together with the carbon to which they are attached to form C(.dbd.O), C(.dbd.S) or C(.dbd.N--OR.sup.15);
provided that when two R.sup.14, groups are attached to a carbon atom which is attached to a SO.sub.2 as in Q-1 and Q-2 above then said R.sup.14 groups are other than taken together as optionally substituted --OCH.sub.2 CH.sub.2 O--, --OCH.sub.2 CH.sub.2 CH.sub.2 O--, --SCH.sub.2 CH.sub.2 S--, or --SCH.sub.2 CH.sub.2 CH.sub.2 S-- and no more than one of said R.sup.14 groups can be C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 haloalkylthio, or hydroxy;
each R.sup.15 is independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, or C.sub.3 -C.sub.6 alkynyl;
each m is independently 0, 1, or 2;
and
each p is independently 1, 2, or 3.

29 more elements

Dependencies are inferred from the claim text.

patentgrep

Loading patent…

Abstract

A compound selected from Formula I, N-oxides and agriculturally-suitable salts thereof, ##STR25## wherein:

Q is phenyl, substituted with R.sup.4 and optionally substituted with up to three R.sup.5 ;
provided that, when R.sup.4 and an adjacently attached R.sup.5 are taken together, then Q is selected from the group ##STR26## A is --CH.sub.2 -- or --CH.sub.2 --CH.sub.2 --, each group optionally substituted with 1-4 halogen;
W is O or S;
R.sup.1 is H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, or C.sub.3 -C.sub.6 cycloalkyl;
R.sup.2 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy, halogen, or cyano;
R.sup.3 is OR.sup.6, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 haloalkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.1 -C.sub.6 haloalkylsulfinyl, C.sub.1 -C.sub.6 alkylsulfonyl, C.sub.1 -C.sub.6 haloalkylsulfonyl, mercapto, or halogen;
R.sup.4 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, OR.sup.7, S(O).sub.m R.sup.8, S(O).sub.2 NR.sup.9 R.sup.10, C(.dbd.O)R.sup.8, C(.dbd.O)OR.sup.8, C(.dbd.O)NR.sup.9 R.sup.10, NR.sup.11 R.sup.12, halogen, cyano, or nitro;
each R.sup.5 is independently C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, OR.sup.7, S(O).sub.m R.sup.8, S(O).sub.2 NR.sup.9 R.sup.10, C(.dbd.O)R.sup.8, C(.dbd.O)OR.sup.8, C(.dbd.O)NR.sup.9 R.sup.10, NR.sup.11 R.sup.12, halogen, cyano, or nitro;
or
R.sup.6 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkoxyalkyl, formyl, C.sub.2 -C.sub.6 alkylcarbonyl, C.sub.2 -C.sub.6 alkoxycarbonyl, C.sub.2 -C.sub.6 alkylamino carbonyl, C.sub.3 -C.sub.7 dialkylaminocarbonyl, C.sub.1 -C.sub.6 alkylsulfonyl, or C.sub.1 -C.sub.6 haloalkylsulfonyl;
or R.sup.6 is benzoyl or phenylsulfonyl, each optionally substituted with C.sub.1 -C.sub.3 alkyl, halogen, cyano, or nitro;
each R.sup.7 is independently C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.4 -C.sub.6 cycloalkylalkyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.5 cyanoalkyl, formyl, C.sub.2 -C.sub.5 alkylcarbonyl, C.sub.2 -C.sub.5 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylsulfonyl, or C.sub.1 -C.sub.4 haloalkylsulfonyl;
each R.sup.8 is independently C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.4 -C.sub.6 cycloalkylalkyl, C.sub.2 -C.sub.6 alkoxyalkyl, or C.sub.2 -C.sub.5 cyanoalkyl;
each R.sup.9 is independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, or C.sub.1 -C.sub.6 alkoxy;
or R.sup.9 is phenyl or benzyl, each optionally substituted on the phenyl ring with C.sub.1 -C.sub.3 alkyl, halogen, cyano, or nitro;
each R.sup.10 is independently H, C.sub. -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, or C.sub.3 -C.sub.6 haloalkynyl;
or
each pair of R.sup.9 and R.sup.10, when attached to the same atom, can independently be taken together as --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --, each group optionally substituted with 1-2 C.sub.1 -C.sub.3 alkyl;
each R.sup.11 is independently H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.4 -C.sub.6 cycloalkylalkyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.5 cyanoalkyl, formyl, C.sub.2 -C.sub.5 alkylcarbonyl, C.sub.2 -C.sub.5 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylsulfonyl, or C.sub.1 -C.sub.4 haloalkylsulfonyl;
each R.sup.12 is independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, or C.sub.1 -C.sub.6 alkoxy;
or R.sup.12 is phenyl or benzyl, each optionally substituted on the phenyl ring with C.sub.1 -C.sub.3 alkyl, halogen, cyano, or nitro;
or
each pair of R.sup.11 and R.sup.12, when attached to the same atom, can independently be taken together as --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --, each group optionally substituted with 1-2 C.sub.1 -C.sub.3 alkyl;
R.sup.13 is H or C.sub.1 -C.sub.4 alkyl;
each R.sup.14 is independently C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 haloalkylthio, hydroxy, or halogen;
or two R.sup.14 bonded to the same carbon atom can be taken together as --OCH.sub.2 CH.sub.2 O--, --OCH.sub.2 CH.sub.2 CH.sub.2 O--, --SCH.sub.2 CH.sub.2 S--, or --SCH.sub.2 CH.sub.2 CH.sub.2 S--, each CH.sub.2 optionally substituted with 1-2 CH.sub.3 or 1-2 halogen;
or two R.sup.14 bonded to the same carbon atom can be taken together with the carbon to which they are attached to form C(.dbd.O), C(.dbd.S) or C(.dbd.N--OR.sup.15);
provided that when two R.sup.14, groups are attached to a carbon atom which is attached to a SO.sub.2 as in Q-1 and Q-2 above then said R.sup.14 groups are other than taken together as optionally substituted --OCH.sub.2 CH.sub.2 O--, --OCH.sub.2 CH.sub.2 CH.sub.2 O--, --SCH.sub.2 CH.sub.2 S--, or --SCH.sub.2 CH.sub.2 CH.sub.2 S-- and no more than one of said R.sup.14 groups can be C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 haloalkylthio, or hydroxy;
each R.sup.15 is independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, or C.sub.3 -C.sub.6 alkynyl;
each m is independently 0, 1, or 2;
and
each p is independently 1, 2, or 3.

29 more elements