Pyrrolidinones herbicides
Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof: wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Q 1 , Q 2 , Y 1 , and Y 2 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.
1. A herbicidal composition comprising a compound selected from Formula 1 N-oxides and salts thereof:
wherein
Q 1 is a phenyl ring substituted with 1 to 3 substituents independently selected from R 7 ;
Q 2 is a phenyl ring substituted with 1 to 3 substituents independently selected from R 10 ;
Y 1 and Y 2 are each O;
R 1 is H, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl;
R 2 , R 3 , R 4 , R 5 and R 6 are each H;
each R 7 and R 10 is independently halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C 1 -C 4 nitroalkyl, C 2 -C 4 nitroalkenyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 haloalkoxyalkyl, C 3 -C 4 cycloalkyl, C 3 -C 4 halocycloalkyl, cyclopropylmethyl, methylcyclopropyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 haloalkenyloxy, C 3 -C 4 alkynyloxy, C 3 -C 4 haloalkynyloxy, C 3 -C 4 cycloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, hydroxy, formyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkylcarbonyloxy, C 1 -C 4 alkylsulfonyloxy, C 1 -C 4 haloalkylsulfonyloxy, formylamino, C 2 -C 4 alkylcarbonylamino, —SF5, —SCN, C 3 -C 4 trialkylsilyl, trimethylsilylmethyl or trimethylsilylmethoxy;
provided that when Q 1 is a phenyl ring and said ring is substituted with IC at both ortho positions relative to the bond to the remainder of Formula 1, then said ring is also independently substituted with IC on at least one additional position; and
at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.
2. The herbicidal composition of claim 1 further comprising at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners.
3. A herbicidal mixture comprising (a) a compound selected from Formula 1, N-oxides and salts thereof:
wherein
Q 1 is a phenyl ring substituted with 1 to 3 substituents independently selected from R 7 ;
Q 2 is a phenyl ring substituted with 1 to 3 substituents independently selected from R 10 ;
Y 1 and Y 2 are each O;
R 1 is H, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl;
R 2 , R 3 , R 4 , R 5 and R 6 are each H;
each R 7 and R 10 is independently halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C 1 -C 4 nitroalkyl, C 2 -C 4 nitroalkenyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 haloalkoxyalkyl, C 3 -C 4 cycloalkyl, C 3 -C 4 halocycloalkyl, cyclopropylmethyl, methylcyclopropyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 haloalkenyloxy, C 3 -C 4 alkynyloxy, C 3 -C 4 haloalkynyloxy, C 3 -C 4 cycloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, hydroxy, formyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkylcarbonyloxy, C 1 -C 4 alkylsulfonyloxy, C 1 -C 4 haloalkylsulfonyloxy, formylamino, C 2 -C 4 alkylcarbonylamino, —SF5, —SCN, C 3 -C 4 trialkylsilyl, trimethylsilylmethyl or trimethylsilylmethoxy;
provided that when Q 1 is a phenyl ring and said ring is substituted with R 7 at both ortho positions relative to the bond to the remainder of Formula 1, then said ring is also independently substituted with R 7 on at least one additional position; and (b) at least one additional active ingredient selected from the group consisting of photosystem II inhibitors, acetohydroxy acid synthase (AHAS) inhibitors, acetyl-CoA carboxylase (ACCase) inhibitors, auxin mimics, 5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, photosystem I electron diverters, protoporphyrinogen oxidase (PPO) inhibitors, glutamine synthetase (GS) inhibitors, very long chain fatty acid (VLCFA) elongase inhibitors, auxin transport inhibitors, phytoene desaturase (PDS) inhibitors, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, homogentisate solanesyltransferase (HST) inhibitors, cellulose biosynthesis inhibitors, other herbicides including mitotic disruptors, organic arsenicals, asulam, bromobutide, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb, herbicide safeners, and salts thereof.
4. The herbicidal mixture of claim 3 , wherein the at least one additional active ingredient is selected from the group consisting of acetohydroxy acid synthase (AHAS) inhibitors, very long chain fatty acid (VLCFA) elongase inhibitors, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, and salts of compounds of, hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, and salts thereof.
5. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound selected from Formula 1, N-oxides and salts thereof:
wherein
Q 1 is a phenyl ring substituted with 1 to 3 substituents independently selected from R 7 ;
Q 2 is a phenyl ring substituted with 1 to 3 substituents independently selected from R 10 ;
Y 1 and Y 2 are each O;
R 1 is H, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl;
R 2 , R 3 , R 4 , R 5 and R 6 are each H;
each R 7 and R 10 is independently halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C 1 -C 4 nitroalkyl, C 2 -C 4 nitroalkenyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 haloalkoxyalkyl, C 3 -C 4 cycloalkyl, C 3 -C 4 halocycloalkyl, cyclopropylmethyl, methylcyclopropyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 haloalkenyloxy, C 3 -C 4 alkynyloxy, C 3 -C 4 haloalkynyloxy, C 3 -C 4 cycloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, hydroxy, formyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkylcarbonyloxy, C 1 -C 4 alkylsulfonyloxy, C 1 -C 4 haloalkylsulfonyloxy, formylamino, C 2 -C 4 alkylcarbonylamino, —SF5, —SCN, C 3 -C 4 tri alkyl silyl, trimethylsilylmethyl or trimethylsilylmethoxy;
provided that when Q 1 is a phenyl ring and said ring is substituted with IC at both ortho positions relative to the bond to the remainder of Formula 1, then said ring is also independently substituted with IC on at least one additional position.
6. A mixture comprising a compound selected from Formula 1, N-oxides and salts thereof:
wherein
Q 1 is a phenyl ring substituted with 1 to 3 substituents independently selected from R 7 ;
Q 2 is a phenyl ring substituted with 1 to 3 substituents independently selected from R 10 ;
Y 1 and Y 2 are each O;
R 1 is H, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl;
R 2 , R 3 , R 4 , R 5 and R 6 are each H;
each R 7 and R 10 is independently halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C 1 -C 4 nitroalkyl, C 2 -C 4 nitroalkenyl, C 2 -C 4 alkoxyalkyl, C 2 -C 4 haloalkoxyalkyl, C 3 -C 4 cycloalkyl, C 3 -C 4 halocycloalkyl, cyclopropylmethyl, methylcyclopropyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 haloalkenyloxy, C 3 -C 4 alkynyloxy, C 3 -C 4 haloalkynyloxy, C 3 -C 4 cycloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, hydroxy, formyl, C 2 -C 4 alkylcarbonyl, C 2 -C 4 alkylcarbonyloxy, C i-C 4 alkylsulfonyloxy, C 1 -C 4 haloalkylsulfonyloxy, formylamino, C 2 -C 4 alkylcarbonylamino, —SF5, —SCN, C 3 -C 4 trialkylsilyl, trimethylsilylmethyl or trimethylsilylmethoxy;
provided that when Q 1 is a phenyl ring and said ring is substituted with IC at both ortho positions relative to the bond to the remainder of Formula 1, then said ring is also independently substituted with R 7 on at least one additional position; and
a compound selected from the group consisting of benzobicyclon, bromobutide, fenquinotrione, metazosulfuron, pethoxamid, pretilachlor, pyrazolynate, pyrazosulfuron-ethyl, pyrimisulfan and triafamone.