Pyrrolidinones as 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 compound of Formula 1:
or a salt thereof,
wherein
Q 1 is a 5- to 6-membered fully unsaturated heterocyclic ring, each ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 S and up to 4 N atoms, each ring optionally substituted with up to 5 substituents independently selected from R 7 on carbon atom ring members and selected from R 9 on nitrogen atom ring members;
Q 2 is a phenyl ring substituted with 1 to 2 substituents independently selected from R 10 ;
Y 1 is O;
Y 2 is O;
R 1 is H or CH 3 ;
R 2 is H;
R 3 is H;
R 4 is H;
R 5 is H;
R 6 is H;
each R 7 is independently halogen or C 1 -C 2 haloalkyl;
each R 9 is CH 3 ;
each R 10 is independently halogen or C 1 haloalkyl;
provided that
when Q 1 comprises a 3-furanyl or 3-pyridinyl ring directly bonded to the remainder of Formula 1, then said ring is substituted with at least one substituent selected from R 7 .
2. A herbicidal composition comprising a compound of claim 1 and at least one component selected from the group consisting of surfactants, solid diluents, and liquid diluents.
3. The herbicidal composition of claim 2 further comprising at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners.
4. A herbicidal mixture comprising (a) the compound of claim 1 and (b) at least one additional active ingredient selected from 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 dioxyenase (HPPD) inhibitors, homogentisate solanesyltransferase (HST) inhibitors, cellulose biosynthesis inhibitors, other herbicides selected from mitotic disruptors, organic arsenicals, asulam, bromobutide, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol, fosamine, foamine-ammonium, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb, and herbicide safeners; and salts thereof.
5. A herbicidal mixture comprising (a) a compound of claim 1 and (b) at least one additional active ingredient selected from acetohydroxy acid synthase (AHAS) inhibitors, very long chain fatty acid (VLCFA) elongase inhibitors, and 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors; and salts thereof.
6. A method for controlling the growth of weeds comprising contacting the weeds or their environment with a herbicidally effective amount of a compound of claim 1 .
7. A mixture comprising a compound of claim 1 and a compound selected from benzobicyclon, bromobutide, fenquinotrione, metazosulturon, pethoxamid, pretilachlor, pyrazolynate, pyrazolsulfuron-ethyl, pyrimisulfan, and triafamone.
8. A compound of Formula 1:
or a salt thereof,
wherein
R v is R 7 or R 9 ; wherein substituent R 7 is on the carbon atom ring members and substituent R 9 is on the nitrogen atom ring members;
r is 1 or 2;
Q 2 is Ph(2,3-di-F) or Ph(2-F);
Y 1 is O;
Y 2 is O;
R 1 is H or CH 3 ;
R 2 is H;
R 3 is H;
R 4 is H;
R 5 is H;
R 6 is H;
each R 7 is independently halogen or C 1 -C 2 haloalkyl; and
each R 9 is CH 3 ,
provided when Q 1 comprises a 3-pyridinyl ring directly bonded to the remainder of Formula 1, then said ring is substituted with at least one substituent selected from R′.
9. The compound of claim 8 , or a salt thereof,
wherein
Q 1 is
10. The compound of claim 8 , or a salt thereof,
wherein
Q 1 is
11. The compound of claim 8 , or a salt thereof,
wherein
Q 1 is
12. The compound of claim 8 , or a salt thereof, wherein Q 2 is Ph(2,3-di-F).
13. The compound of claim 8 , or a salt thereof, wherein Q 2 is Ph(2-F).
14. The compound of claim 8 , or a salt thereof, wherein R 1 is H.
15. The compound of claim 8 , or a salt thereof, wherein R 1 is CH 3 .
16. The compound of claim 8 , or a salt thereof, wherein each R 7 is independently halogen or C haloalkyl.
17. The compound of claim 8 , or a salt thereof, wherein each R 7 is independently halogen or C 1 fluoroalkyl.
18. The compound of claim 8 , or a salt thereof, wherein each R 7 is independently halogen or CF 3 .
19. The compound of claim 8 , or a salt thereof, wherein each R 7 is independently F, Cl, Br or CF 3 .
20. The compound of claim 8 , or a salt thereof, wherein each R 7 is independently F or CF 3 .
21. The compound of claim 8 , or a salt thereof, wherein
Q 1 is
Q 2 is Ph(2,3-di-F), and R 1 is CH 3 .
22. A herbicidal composition comprising a compound of claim 8 and at least one component selected from the group consisting of surfactants, solid diluents, and liquid diluents.
23. The herbicidal composition of claim 22 further comprising at least one additional active ingredient selected from the group consisting of other herbicides and herbicide safeners.
24. A herbicidal mixture comprising (a) the compound of claim 8 and (b) at least one additional active ingredient selected from 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 dioxyenase (HPPD) inhibitors, homogentisate solanesyltransferase (HST) inhibitors, cellulose biosynthesis inhibitors, other herbicides selected from mitotic disruptors, organic arsenicals, asulam, bromobutide, cinmethylin, cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol, fosamine, foamine-ammonium, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb, and herbicide safeners; and salts thereof.
25. A herbicidal mixture comprising (a) a compound of claim 8 and (b) at least one additional active ingredient selected from acetohydroxy acid synthase (AHAS) inhibitors, very long chain fatty acid (VLCFA) elongase inhibitors, and 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors; and salts thereof.
26. A method for controlling the growth of weeds comprising contacting the weeds or their environment with a herbicidally effective amount of a compound of claim 8 .
27. A mixture comprising a compound of claim 8 and a compound selected from benzobicyclon, bromobutide, fenquinotrione, metazosulfuron, pethoxamid, pretilachlor, pyrazolynate, pyrazolsulfuron-ethyl, pyrimisulfan, and triafamone.