WO2012122171A1 - Oxohétérocycles bis-azotés herbicides - Google Patents

Oxohétérocycles bis-azotés herbicides Download PDF

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Publication number
WO2012122171A1
WO2012122171A1 PCT/US2012/027889 US2012027889W WO2012122171A1 WO 2012122171 A1 WO2012122171 A1 WO 2012122171A1 US 2012027889 W US2012027889 W US 2012027889W WO 2012122171 A1 WO2012122171 A1 WO 2012122171A1
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alkyl
compound
independently
haloalkyl
hydroxy
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PCT/US2012/027889
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English (en)
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Andrew Edmund Taggi
Thomas Martin Stevenson
Kanu Maganbhai Patel
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E. I. Du Pont De Nemours And Company
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Publication of WO2012122171A1 publication Critical patent/WO2012122171A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Definitions

  • This invention relates to certain bis-nitrogen oxo heterocycles, their salts and compositions, and methods of their use for controlling undesirable vegetation. This invention also relates to certain intermediates and a method useful for prepaing these bis-nitrogen heterocycles and their salts.
  • the control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, maize, potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different sites of action.
  • R 1 is C 1 -C 6 alkyl
  • R 2 and R 3 are each independently hydrogen, cyano, or nitro
  • A is a A- 1 through A-5 as defined therein as herbicides.
  • This invention is directed to compounds of Formula 1 (including all stereoisomers), N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides:
  • A is a radical selected from the group consisting of
  • B 1 and B 3 are each independently a radical selected from the group consisting of
  • B 2 is a radical selected from the group consisting of
  • Rl is or
  • R 1 is N(R 40 )R 41 ;
  • Rl is -G A or -W 2 G A ;
  • each G A is a 4- to 7-membered carbocyclic ring including ring members selected from
  • each G A is a 9-membered partially saturated fused ring system containing carbon ring members and 2 nitrogen ring members, the ring optionally substituted with up to 2 substituents selected from R 21 on carbon ring members and R 22 on nitrogen ring members;
  • each E 1 , E 2 , and E 3 is independently O, S, NR 28 , NOR 28 , NN(R 28 ) 2 , N-CN or N-N0 2 ; each L is independently O, N(R 31 ) or S;
  • each R 24 , R 25 , R 26 and R 27 is independently hydrogen; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, N0 2 , hydroxy, C 1 -C 4 alkoxy, CJ-C 4 alkylsulfinyl, Q-C 4 alkylsulfonyl, C1-C4 alkylamino, C 2 -C 8 dialkylamino, C 3 -C 6 cycloalkylamino and (C1-C 4 alkyl ⁇ -C 6 cycloalkylamino;
  • each R 28 is independently H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;
  • each R 29 is independently H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylsulfonyl or C 1 -C 6 haloalkylsulfonyl;
  • each Q 1 and Q 2 is independently O, S or N(R 31 );
  • Q 3 is C1-C 4 alkylene optionally substituted with up to 4 substituents selected from C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl and C 3 -C 6 cycloalkyl;
  • R 30 is independently H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl
  • R 31 is independently H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl
  • R 32 is H or C 1 -C 6 alkyl
  • each x is 0, 1 or 2;
  • W 5 is C 1 -C 6 alkylene
  • W 1 is C 1 -C 6 alkylene, C 2 -C 6 alkenylene or C 2 -C 6 alkynylene; or -(CH 2 ) 2 OCH 2 - or -(CH 2 ) 3 OCH 2 -; C 1 -C 6 alkylene;
  • cycloalkylalkyl Cg-C 1 4 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 3 -C 10 alkoxyalkenyl, C 4 -CK) cycloalkoxyalkyl, C 3 -C20 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkylsulfonylalkyl, C 2 -C 8 alkylaminoalkyl, C 3 -CJQ dialkylaminoalkyl, C 2 -C 8 haloalkylaminoalkyl,
  • cycloalkylaminocarbonyl C 2 -C5 cyanoalkyl, C 1 -C 6 hydroxyalkyl, C 4 -CK ) cycloalkenylalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 8 haloalkoxyhaloalkyl, C 4 -C 1 g halocycloalkoxyalkyl, C 4 -C 10
  • cycloalkenyloxyalkyl C4-C1Q halocycloalkenyloxyalkyl, C 3 -C 10 dialkoxyalkyl, C 3 -C 10 alkoxyalkylcarbonyl, C 3 -C 10 alkoxycarbonylalkyl, C 2 -C 8
  • haloalkoxycarbonyl C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C ⁇ -C IQ cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C 6 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 2 -C 8 alkoxyalkoxy, C 2 -C 8 alkylcarbonyloxy, C 2 -C 8 haloalkylcarbonyloxy, C 4 -C 10
  • cycloalkylcarbonyloxy C ⁇ - IQ alkylcarbonylalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6
  • haloalkylsulfinyl C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 3 -C 8 trialkylsilyl, C 3 -C 8 cycloalkenyloxy, C 3 ⁇ C 8 halocycloalkenyloxy, C 2 -C 8 haloalkoxyalkoxy, C 2 -C 8 alkoxyhaloalkoxy, C 2 -C 8 haloalkoxyhaloalkoxy, C 3 -C 10 alkoxycarbonylalkoxy, C 2 -C 8
  • dialkylaminosulfonyl C 3 -C 10 halotrialkylsilyl, C 1 -C 6 alkylamino, C 2 -C 8 dialkylamino, C 1 -Cg haloalkylamino, C 2 -C 8 halodialkylamino, C 3 -C 8 cycloalkylamino, C 2 -C 8 alkylcarbonylamino, C 2 -C 8 haloalkylcarbonylamino, C 1 -Cg alkylsulfonylamino, C 1 -Cg haloalkylsulfonylamino or C 4 -C 10
  • each E 4 , E 5 , and E 6 is independently O, S, NR 37 , NOR 37 , NN(R 37 ) 2 , N-CN or N-N0 2 ; each L 1 is independently O, N(R 38 ) or S;
  • each R 33 , R 34 , R 35 and R 36 is independently hydrogen; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -Cg alkynyl or C 3 -C 6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, N0 2 , hydroxy,
  • each R 37 is independently H, C 1 -Cg alkyl or C 1 -Cg haloalkyl;
  • each Q 4 and Q 5 is independently O, S or N(R 38 );
  • Q 6 is C1-C 4 alkylene optionally substituted with up to 4 substituents selected from C 1 -Cg alkyl, C 2 -Cg alkenyl, C 2 -Cg alkynyl and C 3 -C 6 cycloalkyl;
  • R 38 is independently H, C 1 -Cg alkyl or C 1 -Cg haloalkyl
  • R59 is H or C 1 -C 6 alkyl
  • each y is 0, 1 or 2;
  • W 7 is C 1 -C 6 alkylene
  • W 6 is C 1 -C 6 alkylene, C 2 -C 6 alkenylene or C 2 -C 6 alkynylene; or -(CH 2 ) 2 OCH 2 - or
  • W 3 is C Cg alkylene, C 2 -C 6 alkenylene or C 2 -Cg alkynylene;
  • W 4 is C 1 -C 6 alkylene
  • alkylcarbonylalkoxy C 1 -Cg alkylthio, C 1 -Cg haloalkylthio, C 3 -C 8
  • alkylsulfonyl C 1 -Cg haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 1 -Cg alkylsulfonyloxy, C 1 -Cg alkylamino, C 2 -C 8 dialkylamino, C 1 -Cg
  • haloalkylamino C 2 -C 8 halodialkylamino, C 3 -C 8 cycloalkylamino, C 2 -C 8 alkylcarbonylamino, C 2 -C 8 haloalkylcarbonylamino, C 1 -C 6 alkylsulfonylamino or C 1 -Cg haloalkylsulfonylamino; or benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy, phenyl sulfonyloxy, benzylsulfonyloxy, phenylthio, benzylthio, phenylsulfinyl, benzylsulfinyl, phenylsulfonyl or benzylsulfonyl, each optionally substituted on ring members with up to five substituents selected from R 21 ;
  • M + is an alkali metal cation or an ammonium cation
  • R 4 , R 5 , R 6 and R 7 are each independently H, halogen, hydroxy, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -Cg haloalkyl, C 1 -Cg alkoxy, C 1 -Cg haloalkoxy, C 3 -C 8 cycloalkoxy or C 3 -C 8 halocycloalkoxy; or phenyl or benzyl, each optionally substituted on ring members with up to five substituents selected from R21;
  • R 8 is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6
  • haloalkenyl C 2 -Cg haloalkynyl, C 3 -C 8 cycloalkyl or C 3 -C 8 halocycloalkyl; or benzyl optionally substituted on ring members with up to five substituents selected from R 21 ;
  • R 9 is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6
  • haloalkenyl C 2 -Cg haloalkynyl, C 3 -Cg cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, Cg-C ⁇ cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C5-C22 alkylcycloalkylalkyl, C 3 -Cg cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -Cg alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl or C 2 -Cg alkylthioalkyl;
  • R 10 is H, halogen, cyano, hydroxy, amino, nitro, SH, -S0 2 NH 2 , -S0 2 NHCN,
  • R 1 1 is H, halogen, cyano, hydroxy, amino, C 1 -Cg alkyl, C 2 -Cg alkenyl, C 2 -C 6 alkynyl, C 1 -Cg haloalkyl, C 2 -C 6 haloalkenyl, C -C ⁇ haloalkynyl, C 3 -Cg cycloalkyl, C 3 -C halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 10 alk
  • R 12 is H, halogen, cyano, hydroxy, amino, C 1 -Cg alkyl, C 2 -C alkenyl, C 2 -C 6 alkynyl, C 1 -Cg haloalkyl, C 2 -Cg haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C -C ⁇ cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C5-CJ2 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl or C 2 -Cg alkoxycarbonylamino;
  • R 13 is H, halogen, cyano, hydroxy, amino, nitro or C 2 -C 8 alkoxycarbonyl
  • n 0, 1, or 2;
  • each R 14 , R 15 , R 18 and R 19 is independently H, halogen, cyano, hydroxy or C 1 -Cg alkyl; or
  • R 14 and R 18 is taken together as C 2 -Cg alkylene or C 2 -Cg alkenylene;
  • R 20 is H, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 1 -Cg alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 8 cycloalkyl; T is C 1 -Cg alkylene or C 2 -C alkenylene;
  • each G is independently a 5- or 6-membered heterocyclic ring or an 8-, 9- or
  • cycloalkylalkyl C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -Cg alkylsulfinylalkyl, C 2 -Cg alkoxyhaloalkyl, C 2 -C5 cyanoalkyl, C 1 -Cg hydroxyalkyl, C 1 -Cg alkoxy, C 1 -Cg haloalkoxy, C 3 -Cg cycloalkoxy, C 3 ⁇ Cg halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C alkenyloxy, C 2 -C haloalkenyloxy, C 2 -
  • each R 22 is independently C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C3 ⁇ 4 alkynyl, C 1 -Cg haloalkylthio, C 3 -Cg cycloalkylthio, C 1 -Cg alkylsulfinyl, C 1 -Cg haloalkylsulfinyl, C 1 -Cg alkylsulfonyl, C 1 -Cg haloalkylsulfonyl, C 3 -Cg cycloalkylsulfonyl, C 1 -Cg alkylamino, C 2 -Cg dialkylamino, C ⁇ -Cg haloalkylamino, C 2 -Cg halodialkylamino or C 3 -Cg cycloalkylamino; each R 22 is independently C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C
  • R ° is C 1 -C 6 alkyl
  • R 41 is C 1 -C 6 alkyl
  • This invention pertains to a compound of Formula 1 (including all stereoisomers), an N-oxide, or a salt thereof.
  • This invention also relates to a herbicidal composition comprising a compound of the invention (i.e. in a herbicidally effective amount) and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents.
  • This invention further relates to a method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of the invention (e.g., as a composition described herein).
  • This invention also relates to a herbicidal mixture of (a) a compound of Formula 1 and (b) at least one additional active ingredient.
  • This invention is also directed to an intermediate compound of Formula 1Q (including all stereoisomers), N-oxides, and salts thereof:
  • A' is a radical selected from the group consisting of
  • R 1 , R 2 , B 1 , B 2 , B 3 , T, R 9 and R 10 are as defined above for a compound of Formula 1 which is useful for preparing a compound of Formula 1.
  • This invention is also directed to a compound of Formula 1R (including all stereoisomers), N-oxides, and salts thereof:
  • R 1 is N(R 40 )R 41 ;
  • R 1 is G A ;
  • each E 1 , E 2 and E 3 is independently O, NOR 28 or N(R 28 ) 2 ;
  • L is independently O or N(R 1 );
  • each R 24 , R 25 and R 26 is independently hydrogen; or CJ-C 4 alkyl or C 3 -C 5 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, hydroxy, C1-C 2 alkoxy, alkylsulfinyl and
  • each R 28 is independently H, alkyl or C1-C 3 haloalkyl
  • each R 29 is independently H, C 1 -C 3 alkyl, C1-C 3 haloalkyl, C 1 -C 3 alkylcarbonyl,
  • each Q 1 and Q 2 is independently O or N(R 31 );
  • Q 3 is C 2 -C 3 alkylene optionally substituted with up to 2 substituents selected from C r C 4 alkyl;
  • R 30 is independently H, C r C 3 alkyl or C r C 3 haloalkyl;
  • R 31 is independently H, C 1 -C 3 alkyl or C1-C 3 haloalkyl;
  • R 32 is H or C r C 3 alkyl
  • W 5 is C r C 4 alkylene
  • W 1 is C 2 -C 4 alkylene, -(CH 2 ) 2 OCH 2 - or -(CH 2 ) 3 OCH 2 -;
  • R 2 is phenyl or -W 3 (phenyl), each substituted on ring members with up to two
  • W 3 is C 1 -Cg alkylene, C 2 -C 6 alkenylene or C 2 -Cg alkynylene;
  • each G is independently a 5- or 6-membered heterocyclic ring or an 8-, 9- or
  • cycloalkylalkyl C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -Cg alkoxyalkyl, C 4 -CK) cycloalkoxyalkyl, C 3 -CJQ alkoxyalkoxyalkyl, C 2 -C alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -Cg alkoxyhaloalkyl, C 2 -C5 cyanoalkyl, C 1 -Cg hydroxyalkyl, C 1 -Cg alkoxy, C 1 -Cg haloalkoxy, C 3 -Cg cycloalkoxy, C 3 -Cg halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -Cg alkenyloxy, C 2 -Cg haloalkenyloxy, C 2
  • alkylcarbonyloxy C 1 -Cg alkylthio, C 1 -Cg haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -Cg alkylsulfinyl, C 1 -Cg haloalkylsulfinyl, C 1 -Cg alkylsulfonyl, C 1 -Cg haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 1 -C 6 alkylamino, C 2 -C 8 dialkylamino, C ⁇ Cg haloalkylamino, C 2 -C 8 halodialkylamino or C 3 -C 8 cycloalkylamino;
  • each R 22 is independently C 1 -Cg alkyl, C 2 -Cg alkenyl, C 2 -Cg alkynyl, C ⁇ Cg
  • haloalkyl C 3 -C cycloalkyl or C 2 -C 8 alkoxyalkyl
  • R 40 is C 1 -Cg alkyl
  • R 41 is C 1 -Cg alkyl
  • This invention is also directed to a compound of Formula IS (including all stereoisomers), N-oxides, and salts thereof:
  • R 1 is ;
  • R 1 is N(R 40 )R 41 ;
  • R 1 is G A ;
  • each E 1 , E 2 and E 3 is independently O, NOR 28 or N(R 28 ) 2 ;
  • L is independently O or N(R 31 );
  • each R 24 , R 25 and R 26 is independently hydrogen; or C1-C 4 alkyl or C 3 -C 5 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, hydroxy, C C 2 alkoxy, C 1 -C 2 alkylsulfinyl and C1-C 4 alkylsulfonyl;
  • each R 28 is independently H, C1-C3 alkyl or haloalkyl
  • each R 29 is independently H, C1-C 3 alkyl, C1-C 3 haloalkyl, Ci-C ⁇ alkylcarbonyl, C 1 -C 3 alkylsulfonyl or CJ-C 3 haloalkylsulfonyl;
  • each Q 1 and Q 2 is independently O or N(R 31 );
  • Q 3 is C 2 -C 3 alkylene optionally substituted with up to 2 substituents selected from C r C 4 alkyl;
  • R 30 is independently H, CJ-C 3 alkyl or C!-C 3 haloalkyl;
  • R 31 is independently H, C 1 -C 3 alkyl or C1-C 3 haloalkyl;
  • R 32 is H or C r C 3 alkyl
  • W 5 is C r C 4 alkylene
  • W 1 is C 2 -C 4 alkylene, -(CH 2 ) 2 OCH 2 - or -(CH 2 ) 3 OCH 2 -;
  • R 2 is phenyl or -W 3 (phenyl), each substituted on ring members with up to two
  • R 21 substituents selected from R 21 ; or -G; or C 1 -Cg alkyl or C 3 -C 8 cycloalkyl;
  • W 3 is C 1 -Cg alkylene, C 2 -C 6 alkenylene or C 2 -Cg alkynylene;
  • each G is independently a 5- or 6-membered heterocyclic ring or an 8-, 9- or
  • alkylcarbonyloxy C 1 -Cg alkylthio, C 1 -Cg haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -Cg alkylsulfinyl, C 1 -Cg haloalkylsulfinyl, C 1 -Cg alkylsulfonyl, C 1 -Cg haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 1 -C 6 alkylamino, C 2 -C 8 dialkylamino, C ⁇ Cg haloalkylamino, C 2 -C 8 halodialkylamino or C 3 -C 8 cycloalkylamino;
  • each R 22 is independently C 1 -Cg alkyl, C 2 -Cg alkenyl, C 2 -Cg alkynyl, C ⁇ Cg
  • R 23 is an optionally substituted carbon moiety
  • R 40 is C 1 -Cg alkyl
  • R 41 is C 1 -Cg alkyl
  • compositions comprising, “comprising,” “includes,” “including,” “has,” “having,” “contains”, “containing,” “characterized by” or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated.
  • a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method.
  • transitional phrase consisting essentially of is used to define a composition or method that includes materials, steps, features, components, or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components, or elements do not materially affect the basic and novel characteristic(s) of the claimed invention.
  • a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).
  • seedling used either alone or in a combination of words means a young plant developing from the embryo of a seed.
  • alkylating agent refers to a chemical compound in which a carbon-containing radical is bound through a carbon atom to a leaving group such as halide or sulfonate, which is displaceable by bonding of a nucleophile to said carbon atom. Unless otherwise indicated, the term “alkylating” does not limit the carbon-containing radical to alkyl; the carbon-containing radicals in alkylating agents include the variety of carbon-bound substituent radicals specified for R 1 , R 2 and R 3 .
  • de-alkylating agent refers to a reagent that cleaves a carbon-carbon or carbon-oxygen bond.
  • alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, «-propyl, z ' -propyl, or the different butyl, pentyl or hexyl isomers.
  • Alkenyl includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers.
  • Alkenyl also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl.
  • Alkynyl includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers.
  • Alkynyl can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
  • Alkylene denotes a straight-chain or branched alkanediyl.
  • alkylene examples include CH 2 , CH 2 CH 2 , CH(CH 3 ), CH 2 CH 2 CH 2 , CH 2 CH(CH 3 ) and the different butylene isomers.
  • Alkenylene denotes a straight-chain or branched alkenediyl containing one olefinic bond.
  • Alkynylene denotes a straight-chain or branched alkynediyl containing one triple bond. Examples of “alkynylene” include C ⁇ C, CH 2 C ⁇ C, C ⁇ CCH 2 and the different butynylene isomers.
  • Alkoxy includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.
  • Alkoxyalkyl denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” include CH 3 OCH 2 , CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 , CH 3 CH 2 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
  • Alkoxyalkoxy denotes alkoxy substitution on alkoxy.
  • Alkenyloxy includes straight-chain or branched alkenyloxy moieties.
  • alkynyloxy includes straight-chain or branched alkynyloxy moieties. Examples of “alkynyloxy” include HC ⁇ CCH 2 0, CH 3 C ⁇ CCH 2 0 and CH 3 C ⁇ CCH 2 CH 2 0.
  • Alkoxyalkenyl includes straight-chain or branched alkenyl substituted by an alkoxy group.
  • Alkoxyalkoxyalkyl denotes alkoxyalkoxy substitution on alkyl.
  • alkoxyalkoxyalkyl examples include CH 3 OCH 2 OCH 2 , CH 3 OCH 2 OCH 2 CH 2 , CH 3 CH 2 OCH 2 OCH 2 and CH 3 OCH3CH 2 OCH2CH 2 .
  • Alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.
  • Alkylsulfmyl includes both enantiomers of an alkylsulfinyl group. Examples of “alkylsulfinyl” include CH 3 S(0)-, CH 3 CH 2 S(0)-, CH 3 CH 2 CH 2 S(0)-, (CH 3 ) 2 CHS(0)- and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers.
  • alkylsulfonyl examples include CH 3 S(0) 2 -, CH 3 CH 2 S(0) 2 -, CH 3 CH 2 CH 2 S(0) 2 -, (CH 3 ) 2 CHS(0) 2 -, and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers.
  • cycloalkylsulfinyl and “cycloalkylsulfonyl are defined analogously to the terms “alkylsulfinyl” and “alkylsulfonyl” above.
  • Alkyl thioalkyl denotes alkylthio substitution on alkyl.
  • alkylthioalkyl include CH 3 SCH 2 , CH 3 SCH 2 CH 2 , CH 3 CH 2 SCH 2 , CH 3 CH 2 CH 2 CH 2 SCH 2 and CH 3 CH 2 SCH 2 CH 2 ;
  • alkylsulfinylalkyl and “alkylsulfonylalkyl” include the corresponding sulfoxides and sulfones, respectively.
  • Alkylamino includes an NH radical substituted with straight-chain or branched alkyl.
  • alkylamino examples include CH 3 CH 2 NH, CH 3 CH 2 CH 2 NH, and (CH 3 ) 2 CHCH 2 NH.
  • dialkylamino examples include (CH 3 ) 2 N, (CH 3 CH 2 CH 2 ) 2 N and CH 3 CH 2 (CH 3 )N.
  • Alkylaminoalkyl denotes alkylamino substitution on alkyl. Examples of “alkylaminoalkyl” include CH 3 NHCH 2 , CH 3 NHCH 2 CH 2 , CH 3 CH 2 NHCH 2 , CH 3 CH 2 CH 2 CH 2 NHCH 2 and CH 3 CH 2 NHCH 2 CH 2 .
  • dialkylaminoalkyl examples include ((CH 3 ) 2 CH) 2 NCH 2 , (CH 3 CH 2 CH 2 ) 2 NCH 2 and CH 3 CH 2 (CH 3 )NCH 2 CH 2 .
  • Alkylcarbonylthio denotes a straight-chain or branched alkylcarbonyl attached to and linked through a sulfur atom.
  • alkyl(thiocarbonyl)oxy denotes an alkyl group bonded to a thiocarbonyl moiety attached to and linked through an oxygen atom.
  • alkyl(thiocarbonyl)thio refers to an alkyl group bonded to a sulfur atom.
  • Trialkylsilyl includes 3 branched and/or straight-chain alkyl radicals attached to and linked through a silicon atom, such as trimethylsilyl, triethylsilyl and tert-butyldimethylsilyl.
  • halotrialkylsilyl include CF 3 (CH 3 ) 2 Si-, (CF 3 ) 3 Si-, and CH 2 Cl(CH 3 ) 2 Si-.
  • Hydroalkyl denotes an alkyl group substituted with one hydroxy group. Examples of “hydroxyalkyl” include HOCH 2 CH 2 , CH 3 CH 2 (OH)CH and HOCH 2 CH 2 CH 2 CH 2 .
  • Cyanoalkyl denotes an alkyl group substituted with one cyano group. Examples of “cyanoalkyl” include NCCH 2 , NCCH 2 CH 2 and CH 3 CH(CN)CH 2 .
  • Cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • alkylcycloalkyl denotes alkyl substitution on a cycloalkyl moiety and includes, for example, ethyl cyclopropyl, z ' -propylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl.
  • cycloalkylalkyl denotes cycloalkyl substitution on an alkyl moiety.
  • cycloalkylalkyl examples include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups.
  • cycloalkoxy denotes cycloalkyl linked through an oxygen atom such as cyclopentyloxy and cyclohexyloxy.
  • alkylcycloalkyl denotes alkyl substitution on a cycloalkyl moiety.
  • alkylcycloalkyl examples include methylcyclopropyl, ethylcyclopentyl, and other straight-chain or branched alkyl groups bonded to cycloalkyl moiety.
  • alkoxycycloalkyl denotes alkoxy substitution on a cycloalkyl moiety.
  • alkoxycycloalkyl include methoxycyclopropyl, ethoxycyclopentyl and other straight -chain or branched alkoxy groups bonded to a cycloalkyl moiety.
  • Cycloalkylalkoxy denotes cycloalkylalkyl linked through an oxygen atom attached to the alkyl chain.
  • Examples of “cycloalkylalkoxy” include cyclopropylmethoxy, cyclopentylethoxy, and other cycloalkyl moieties bonded to straight-chain or branched alkoxy groups.
  • cyanocycloalkyl examples include 4-cyanocyclohexyl and 3-cyanocyclopentyl.
  • Cycloalkenyl includes groups such as cyclopentenyl and cyclohexenyl as well as groups with more than one double bond such as 1,3- and 1 ,4-cyclohexadienyl.
  • halogen either alone or in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” or “alkyl substituted with halogen” include F 3 C-, C1CH 2 -, CF 3 CH 2 - and CF 3 CC1 2 -.
  • halocycloalkyl halocycloalkyl
  • haloalkenyloxy haloalkynyloxy
  • haloalkenyl haloalkynyloxy
  • haloalkoxyalkyl haloalkoxyalkoxy
  • haloalkoxyhaloalkoxy haloalkoxyhaloalkoxy
  • haloalkoxyhaloalkyl haloalkylamino
  • haloalkylaminoalkyl halocycloalkoxy
  • halocycloalkylalkyl halocycloalkenyl
  • halocycloalkenyloxy halocycloalkenyloxyalkyl
  • alkoxyhaloalkoxy alkoxyhaloalkyl, haloalkyl,
  • haloalkoxy examples include CF3O-, CC1 3 CH 2 0-, HCF 2 CH 2 CH 2 0- and CF 3 CH 2 0-.
  • haloalkylthio examples include CC1 3 S-, CF 3 S-, CC1 3 CH 2 S- and C1CH 2 CH 2 CH 2 S-.
  • haloalkylsulfmyl examples include CF 3 S(0)-, CC1 3 S(0)-, CF 3 CH 2 S(0)- and CF 3 CF 2 S(0)-.
  • haloalkylsulfonyl examples include CF 3 S(0) 2 -, CC1 3 S(0) 2 -, CF 3 CH 2 S(0) 2 - and CF 3 CF 2 S(0) 2 -.
  • haloalkynyl examples include HCsCCHCl-, CF 3 CsC-, CC1 3 C ⁇ C- and FCH 2 C ⁇ CCH 2 -.
  • haloalkoxyalkoxy examples include CF 3 OCH 2 0-, C1CH 2 CH 2 0CH 2 CH 2 0-, Cl 3 CCH 2 OCH 2 0- as well as branched alkyl derivatives.
  • haloalkylamino examples include CF 3 (CH 3 )CHNH, (CF 3 ) 2 CHNH and CH 2 C1CH 2 NH.
  • halodialkyl either alone or in compound words such as “halodialkylamino" means at least one of the two alkyl groups is substituted with at least one halogen atom, and independently each halogenated alkyl group may be partially or fully substituted with halogen atoms which may be the same or different.
  • halodialkylamino examples include (BrCH 2 CH 2 ) 2 N and BrCH 2 CH 2 (ClCH 2 CH 2 )N.
  • haloalkylcarbonyl "haloalkoxycarbonyl”, “alkoxyalkylcarbonyl”, “cycloalkoxycarbonyl”, “cycloalkylalkoxycarbonyl” and “cycloalkylaminocarbonyl” are defined analogously.
  • alkylcarbonylalkoxy denotes alkylcarbonyl bonded to an alkoxy moiety.
  • cycloalkylcarbonyloxy denotes a cycloalkylcarbonyl group bonded to oxygen.
  • Examples of “cycloalkylcarbonyloxy” include cyclopropyl-C(0)0- and cyclohexyl-C(0)0-.
  • Alkylsulfonylamino denotes an NH radical substituted with alkylsulfonyl.
  • alkylsulfonyloxy denotes an alkylsulfonyl group bonded to an oxygen atom.
  • cycloalkoxyalkyl denotes cycloalkoxy substitution on an alkyl moiety.
  • examples of “cycloalkoxyalkyl” include cyclopropyloxymethyl, cyclopentyloxyethyl, and other cycloalkoxy moieties bonded to straight-chain or branched alkyl groups.
  • cycloalkylthio denotes cycloalkyl attached to and linked through a sulfur atom such as cyclopropylthio and cyclopentylthio;
  • cycloalkylsulfonyl includes the corresponding sulfones.
  • Alkylcycloalkylalkyl denotes an alkyl group substituted with alkylcycloalkyl.
  • alkylcycloalkylalkyl include 1-, 2-, 3- or 4-methyl or -ethyl cyclohexylmethyl.
  • cycloalkoxyalkoxyalkyl denotes a cycloalkoxy moiety attached to the alkoxy moiety of an alkoxyalkyl group.
  • Examples of the term “cycloalkoxyalkoxyalkyl” include (cyclopropyl)OCH 2 OCH 2 -,
  • cycloalkylcycloalkyl denotes cycloalkyl substitution on another cycloalkyl ring, wherein each cycloalkyl ring independently has from 3 to 7 carbon atom ring members.
  • cycloalkylcycloalkyl examples include cyclopropylcyclopropyl (such as ⁇ , ⁇ -bicyclopropyl-l-yl, l,l'-bicyclopropyl-2-yl), cyclohexylcyclopentyl (such as 4-cyclopentylcyclohexyl) and cyclohexylcyclohexyl (such as ⁇ , -bicyclohexyl-l-yl), and the different cis- and fr «5-cycloalkylcycloalkyl isomers, (such as (1 ?,2S)-l, -bicyclopropyl-2-yl and ( 1 R,2R)- 1 , 1 '-bicyclopropyl-2-yl) .
  • Dialkoxyalkyl denotes two independent alkoxy groups substituted on same carbon of the alkyl group. Examples of “dialkoxyalkyl” include (CH 3 0) 2 CH- and CH 3 CH 2 0(CH 3 0)CH-.
  • Cycloalkylamino denotes an NH radical substituted with cycloalkyl. Examples of “cycloalkylamino” include cyclopropylamino and cyclohexylamino.
  • Cycloalkyl(alkyl)amino means a cycloalkylamino group where the hydrogen atom is replaced by an alkyl radical.
  • cycloalkyl(alkyl)amino examples include groups such as cyclopropyl(methyl)amino, cyclobutyl(butyl)amino, cyclopentyl(propyl)amino, cyclohexyl(methyl)amino and the like.
  • cycloalkylaminoalkyl denotes cycloalkylamino substitution on an alkyl group.
  • Examples of “cycloalkylaminoalkyl” include cyclopropylaminomethyl, cyclopentylaminoethyl, and other cycloalkylamino moieties bonded to straight-chain or branched alkyl groups.
  • Examples of “cycloalkylalkoxycarbonyl” include cyclopropylethoxycarbonyl and cyclopentylmethoxycarbonyl.
  • Cycloalkylcarbonyloxy denotes cycloalkylcarbonyl attached to and linked through an oxygen atom. Examples of “cycloalkylcarbonyloxy” include cyclohexylcarbonyloxy and cyclopentylcarbonyloxy.
  • cycloalkenylalkyl denotes cycloalkenyl substitution on an alkyl moiety.
  • cycloalkenylalkyl examples include cyclobutenylmethyl, cyclopentenylethyl, and other cycloalkenyl moieties bonded to straight-chain or branched alkyl groups.
  • cycloalkenyloxy denotes cycloalkenyl linked through an oxygen atom such as cyclopentenyloxy and cyclohexenyloxy.
  • cycloalkenyloxyalkyl denotes cycloalkenyloxy substitution on an alkyl moiety.
  • cycloalkenyloxyalkyl examples include cyclobutenyloxymethyl, cyclopentenyloxyethyl, and other cycloalkenyloxy moieties bonded to straight-chain or branched alkyl groups.
  • alkylaminosulfonyl denotes a straight-chain or branched alkylamino moiety bonded to a sulfonyl group.
  • alkylaminosulfonyl examples include CH 3 NHS(0) 2 - or CH 3 CH 2 CH 2 NHS(0) 2 -.
  • dialkylaminosulfonyl denotes a straight-chain or branched dialkylamino moiety bonded to a sulfonyl group.
  • Examples of a “dialkylaminosulfonyl” group include (CH 3 ) 2 NS(0) 2 - or (CH 3 CH 2 CH 2 ) 2 NS(0) 2 -.
  • C1-C4 alkylsulfonyl designates methylsulfonyl through butylsulfonyl
  • C 2 alkoxyalkyl designates CH 3 OCH 2 -
  • C 3 alkoxyalkyl designates, for example, CH 3 CH(OCH 3 )-, CH 3 OCH 2 CH 2 - or CH 3 CH 2 OCH 2 -
  • C 4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 - and CH 3 CH 2 OCH 2 CH 2 -.
  • said substituents are independently selected from the group of defined substituents, e.g., (R V ) R , r is 1, 2, 3, 4 or 5 in U-l of Exhibit 3.
  • a group contains a substituent which can be hydrogen, for example R 2 , R3, R4 R5, R6, R7 ? RS, R9 ? RW RU R 12 ? R H R14 R15 ; RIS, R19 OR R 20 ? THEN when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted.
  • variable group When a variable group is shown to be optionally attached to a position, for example (R V ) R in Q-29 of Exhibit 2 then hydrogen may be at the position (i.e. when r is 0) even if not recited in the variable group definition.
  • hydrogen atoms When one or more positions on a group are said to be "not substituted” or “unsubstituted”, then hydrogen atoms are attached to take up any free valency.
  • a "ring” or “ring system” as a component of Formula 1 is carbocyclic or heterocyclic.
  • the term “ring system” denotes two or more fused rings.
  • the terms “bicyclic ring system” and “fused bicyclic ring system” denote a ring system consisting of two fused rings, in which either ring can be saturated, partially unsaturated, or fully unsaturated unless otherwise indicated.
  • the term “spirocyclic ring system” denotes two rings fused at a single atom, and can be either carbospirocyclic or heterospirocyclic.
  • carbocyclic ring denotes a ring or ring system wherein the atoms forming the ring backbone are selected only from carbon.
  • a carbocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring.
  • saturated carbocyclic refers to a ring having a backbone consisting of carbon atoms linked to one another by single bonds; unless otherwise specified, the remaining carbon valences are occupied by hydrogen atoms.
  • heterocyclic ring denotes a ring or ring system in which at least one atom forming the ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur.
  • a heterocyclic ring contains no more than 4 nitrogen atoms, no more than 2 oxygen atoms and no more than 2 sulfur atoms.
  • a heterocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring. When a fully unsaturated heterocyclic ring satisfies Hiickel's rule, then said ring is also called a "heteroaromatic ring” or “aromatic heterocyclic ring”.
  • heterocyclic rings and ring systems can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
  • Aromatic indicates that each of the ring atoms is essentially in the same plane and has a ⁇ -orbital perpendicular to the ring plane, and that (4n + 2) ⁇ electrons, where n is a positive integer, are associated with the ring to comply with Hiickel's rule.
  • aromatic ring system denotes a carbocyclic or heterocyclic ring system in which at least one ring of the ring system is aromatic.
  • G A can be (among others) a 6- to 12-membered saturated or partially saturated carbospirocyclic or heterospirocyclic ring system optionally including ring members, each ring or ring system optionally substituted with up to five substituents as defined in the Summary of the Invention (i.e. R 21 or R 22 ).
  • G A is a 9-membered partially saturated fused ring system containing carbon ring members and 2 nitrogen ring members
  • the ring can be optionally substituted with up to 2 substituents selected from R 21 on carbon ring members and R 22 on nitrogen ring members.
  • Exhibit 1A shows examples of examples of 9-membered partially saturated fused ring systems containing carbon ring members and 2 nitrogen ring members and are optionally substituted by R v (i.e. R 21 or R 22 ). Note that when the attachment point on the T group is illustrated as floating, the T group can be attached to the remainder of Formula 1 through any available carbon or nitrogen of the T group by replacement of a hydrogen atom.
  • G When G is a 5- or 6-membered heterocyclic ring, it may be attached to the remainder of Formula 1 through any available carbon or nitrogen ring atom, unless otherwise described.
  • G When G is (among others) a 5- or 6-membered heterocyclic ring it may be saturated or unsaturated, optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary of the Invention.
  • Examples of a 5- or 6-membered heterocyclic ring optionally substituted with from one or more substituents include the rings Q- 1 through Q-60 illustrated in Exhibit 2 wherein R v is the optional substituent and is any substituent as defined in the Summary of the Invention for R 21 on carbon ring members or R 22 on nitrogen ring members, and r is an integer from 0 to 4, limited by the number of available positions on each Q group.
  • Q-29, Q-30, Q-36, Q-37, Q-38, Q-39, Q-40, Q-41, Q-42 and Q-43 have only one available position, for these Q groups r is limited to the integers 0 or 1, and r being 0 means that the Q group is unsubstituted and a hydrogen is present at the position indicated by (R v ) r .
  • G is a 5- or 6-membered heterocyclic ring optionally substituted with one or more substituents selected from the group of substituents as defined in the Summary of the Invention for R 21
  • one or two carbon ring members of the heterocycle can optionally be in the oxidized form of a carbonyl moiety.
  • Examples of a 5- or 6-membered heterocyclic ring include the rings U-l through U-36 as illustrated in Exhibit 3. Note that when the attachment point on the U group is illustrated as floating, the U group can be attached to the remainder of Formula 1 through any available carbon or nitrogen of the U group by replacement of a hydrogen atom.
  • the optional substituents corresponding to R v can be attached to any available carbon or nitrogen by replacing a hydrogen atom.
  • r is typically an integer from 0 to 4, limited by the number of available positions on each U group.
  • G comprises a ring selected from U-29 through U-36
  • U 2 is selected from O, S or N.
  • the nitrogen atom can complete its valence by substitution with either H or the substituents corresponding to R v as defined in the Summary of the Invention for U (i.e. R 22 ).
  • G can be (among others) an 8-, 9- or 10-membered fused bicyclic ring system optionally substituted with one or more substituents selected from a group of substituents as defined in the Summary of the Invention (i.e. R 21 or R 22 ).
  • Examples of 8-, 9- or 10-membered fused bicyclic ring system optionally substituted with from one or more substituents include the rings Q-81 through Q-123 illustrated in Exhibit 4 wherein R v is any substituent as defined in the Summary of the Invention for G (i.e. R 21 or R 22 ), and r is typically an integer from 0 to 4.
  • R v groups are shown in the structures Q-l through Q-60 and Q-81 through Q-123, it is noted that they do not need to be present since they are optional substituents.
  • the nitrogen atoms that require substitution to fill their valence are substituted with H or R v .
  • (R v ) r can be attached to any available carbon atom or nitrogen atom of the Q group.
  • the Q group can be attached to the remainder of Formula 1 through any available carbon or nitrogen of the Q group by replacement of a hydrogen atom.
  • some Q groups can only be substituted with less than 4 R v groups (e.g., Q-l through Q-5, Q-7 through Q-48, and Q-52 through Q-60).
  • Compounds of this invention can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
  • the compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form.
  • a compound of Formula 1 when a compound of Formula 1 is identified by A being A-l, A-2 or A-3, and the R 3 variable being -SH, then said compound of Formula 1 can exist as a "di-keto thioketo" tautomer, a "di-keto thioenol” tautomer or a "keto thioketo enol” tautomer, or a combination thereof.
  • a compound of Formula 1Q wherein A' is A'-l, A'-2 or A'-3 can be present as a "di-ketone" tautomer or two possible “keto enol” tautomers, or a combination thereof.
  • acyclic enols e.g., the fragment A-7 in the definition of the variable A
  • tautomers represent functionally equivalent species, and identification of a compound by one tautomer is to be considered reference to all possible tautomers of the compound unless otherwise indicated
  • Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts.
  • Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types).
  • polymorph refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice.
  • polymorphs can have the same chemical composition, they can also differ in composition due the presence or absence of co-crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability.
  • a polymorph of a compound of Formula 1 can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound of Formula 1.
  • Preparation and isolation of a particular polymorph of a compound of Formula 1 can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures.
  • nitrogen-containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen-containing heterocycles which can form N-oxides.
  • nitrogen-containing heterocycles which can form N-oxides.
  • tertiary amines can form N-oxides.
  • N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and /n-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as i-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane.
  • MCPBA peroxy acids
  • alkyl hydroperoxides such as i-butyl hydroperoxide
  • sodium perborate sodium perborate
  • dioxiranes such as dimethyldioxirane
  • salts of chemical compounds are in equilibrium with their corresponding nonsalt forms, salts share the biological utility of the nonsalt forms.
  • the salts of a compound of Formula 1 include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • salts also include those formed with organic or inorganic bases such as pyridine, triethylamine or ammonia, or amides, hydrides, hydroxides or carbonates of sodium, potassium, lithium, calcium, magnesium or barium. Accordingly, the present invention comprises compounds selected from Formula 1, N-oxides and agriculturally suitable salts thereof.
  • Embodiments of the present invention as described in the Summary of the Invention also include (where Formula 1 as used in the following Embodiments includes N-oxides and salts thereof):
  • Embodiment 1 A compound of Formula 1 as described in the Summary of the
  • A is A-l, A-3, A-4, A-5 or A-6.
  • Embodiment 2 A compound of Embodiment 1 wherein A is A-l, A-3, A-5 or A-6.
  • Embodiment 3. A compound of Embodiment 2 wherein A is A-l, A-3 or A-5.
  • Embodiment 4 A compound of Embodiment 3 wherein A is A-l or A-3.
  • Embodiment 5 A compound of Embodiment 4 wherein A is A- 1.
  • Embodiment 6 A compound of Embodiment 4 wherein A is A-3.
  • Embodiment 7 A compound of Formula 1 or any one of Embodiments 1 through 4 wherein A is other than A-l .
  • Embodiment 8 A compound of Formula 1 or any one of Embodiments 1 through 7 wherein B 1 is C- 1.
  • Embodiment 9 A compound of Formula 1 or any one of Embodiments 1 through 7 wherein B 1 is C-2.
  • Embodiment 10 A compound of Formula 1 or any one of Embodiments 1 through 9 wherein B 2 is C-3.
  • Embodiment 11 A compound of Formula 1 or any one of Embodiments 1 through 9 wherein B 2 is C-4.
  • Embodiment 12 A compound of Formula 1 or any one of Embodiments 1 through 11 wherein B 3 is C-l.
  • Embodiment 13 A compound of Formula 1 or any one of Embodiments 1 through 11 wherein B 3 is C-2.
  • Embodiment 14 A compound of Formula 1 or any one of Embodiments 1 through 13 wherein R 1 is
  • R 1 is -G A or -W G A .
  • Embodiment 15 A compound of Formula 1 or any one of Embodiments 1 through 14 wherein R 1 is
  • Embodiment 16 A compound of Embodiment 15 wherein each Q 1 and Q 2 is
  • Embodiment 17 A compound of Embodiment 16 wherein each Q 1 and Q 2 is O.
  • Embodiment 18 A compound of Formula 1 or any one of Embodiments 1 through 17 wherein Q 3 is C 2 -C 3 alkylene optionally substituted with up to 4 substituents selected from C C 4 alkyl.
  • Embodiment 19 A compound of Embodiment 18 wherein Q 3 is C 2 -C 3 alkylene optionally substituted with up to 2 substituents selected from C J-C 2 alkyl.
  • Embodiment 20 A compound of Embodiment 19 wherein Q 3 is C 2 -alkylene
  • Embodiment 21 A compound of Embodiment 20 wherein Q 3 is C 2 -alkylene
  • Embodiment 22 A compound of Formula 1 or any one of Embodiments 1 through 21 wherein W 5 is C r C 4 alkylene.
  • Embodiment 22 A A compound of Formula 1 or any one of Embodiments 1 through
  • Embodiment 22 wherein W 5 is C 2 -C 3 alkylene.
  • Embodiment 22B A compound of Embodiment 22 wherein W 5 is C 2 alkylene or C 3 alkylene.
  • Embodiment 23 A compound of Formula 1 or any one of Embodiments 1 through 22 wherein R 32 is H or CJ-C 3 alkyl.
  • Embodiment 23A A compound of Embodiment 23 wherein R 32 is H or methyl.
  • Embodiment 24 A compound of Embodiment 23 wherein R 32 is H.
  • Embodiment 25 A compound of Embodiment 23 wherein R 32 is i-C ⁇ alkyl.
  • Embodiment 26 A compound of Embodiment 25 wherein R 32 is methyl.
  • Embodiment 30 A compound of Formula 1 or any one of Embodiments 1 through 14 or 26A through 29 wherein each E 1 , E 2 , and E 3 is independently O, NOR 28 or
  • Embodiment 31 A compound of Embodiment 27 wherein E 1 is O.
  • Embodiment 32 A compound of Embodiment 27 wherein E 1 is NOR 28 .
  • Embodiment 33 A compound of Embodiment 27 wherein E 1 is NN(R 28 )2- Embodiment 34. A compound of Embodiment 28 wherein E 2 is O.
  • Embodiment 35 A compound of Embodiment 28 wherein E 2 is NOR 28 .
  • Embodiment 36 A compound of Embodiment 28 wherein E 2 is NN(R 8 ) 2 .
  • Embodiment 37 A compound of Embodiment 29 wherein E 3 is O.
  • Embodiment 38 A compound of Embodiment 29 wherein E 3 is NOR 28 .
  • Embodiment 39 A compound of Embodiment 29 wherein E 3 is NN(R 28 ) 2 .
  • Embodiment 39A A compound of Formula 1 or any of Embodiments 1 through 39 wherein each R 28 is independently H, Ci -C 3 alkyl or C 1 -C 3 haloalkyl.
  • Embodiment 40 A compound of Formula 1 or any one of Embodiments 26A, 28, 29 or 34 through 39 wherein each L is independently O or N(R 31 ); provided when E 3 is O, L is other than O.
  • Embodiment 41 A compound of Embodiment 40 wherein L is O.
  • Embodiment 42 A compound of Embodiment 40 wherein L is N(R 31 ).
  • Embodiment 42 A A compound of Embodiment 40 or 42 wherein R 31 is
  • Embodiment 42B A compound of Formula 1 or any one of Embodiments 1 through 42 wherein W 1 is C 2 -C 4 alkylene, -(CH 2 ) 2 OCH 2 - or -(CH 2 ) 3 OCH 2 -.
  • Embodiment 43 A compound Embodiments 42B wherein W 1 is C 1 -C 4 alkylene.
  • Embodiment 43 B A compound of Formula 1 or any one of Embodiments 1 through 42 wherein W 2 is C 1 -C 3 alkylene.
  • Embodiment 44 A compound of Formula 1 or any one of Embodiments 1 through 14 or 27 through 39 wherein each R 24 , R 25 and R 26 is independently hydrogen; or C 1 -C 4 alkyl or C 3 -C5 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, hydroxy, C 1 -C 2 alkoxy, C 1 -C 2 alkylsulfinyl and C j -C 4 alkylsulfonyl.
  • Embodiment 45 A compound of Embodiment 44 wherein each R 24 , R 25 and R 26 is independently hydrogen; or C 1 -C 2 alkyl or C 3 -C 4 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, hydroxy and C 1 -C 2 alkoxy.
  • Embodiment 46 A compound of Formula 1 or any one of Embodiments 1 through 14 wherein R 1 is -G A .
  • Embodiment 47 A compound of Formula 1 or any one of Embodiments 1 through 14 wherein R 1 is -W 2 G A .
  • Embodiment 47 A A compound of any one of Embodiments 46 or 47 wherein each G A is a 4- to 7-membered carbocyclic ring including ring members selected from
  • Embodiment 49 A A compound of any one of Embodiments 47 A through 49 wherein each R 29 is independently H, C1-C 3 alkyl, C1-C 3 haloalkyl, C1-C 3
  • alkylcarbonyl C ⁇ C ⁇ alkylsulfonyl or Q-C 3 haloalkylsulfonyl.
  • Embodiment 49B A compound of Embodiment 49A wherein each R 29 is
  • Embodiment 49C A compound of any one of Embodiments 47A through 49 wherein R 30 is independently H, C r C 3 alkyl or C r C 3 haloalkyl.
  • Embodiment 50 A compound of Formula 1 or Embodiment 47 A wherein G A is a 6- to 12-membered saturated or partially saturated carbospirocyclic or
  • Embodiment 50A A compound of Embodiment 50 wherein G A is a 9- to
  • Embodiment 50B A compound of Embodiment 50 wherein R 30 is independently H, C r C 3 alkyl or C r C 3 haloalkyl.
  • Embodiment 50C A compound of Embodiment 50 wherein each R 29 is C Cg alkyl, C 1 -Cg haloalkyl, C 1 -Cg alkylcarbonyl.
  • Embodiment 51 A compound of Embodiment 50A wherein G A is selected from
  • r is 0 to 3; and R v is selected from R 21 .
  • Embodiment 52 A compound of Embodiment 51 wherein G A is selected from G A -1, G A -2, G A -3, G A -7, G A -8 and G A -9.
  • Embodiment 53 A compound of Embodiment 52 wherein G A is selected from G A -2 and G A -3.
  • Embodiment 53 A A compound of Embodiment 53 wherein G A is G A -2.
  • Embodiment 53B A compound of Formula 1 or any one of Embodiments 1 throuh 53A wherein each G A is other than a 9-membered partially saturated fused ring system containing carbon ring members and 2 nitrogen ring members, the ring optionally substituted with up to 2 substituents selected from R 21 on carbon ring members and R 22 on nitrogen ring members.
  • Embodiment 53C A compound of Formula 1 or any one of Embodiments 1 through 47 wherein each G A is a 9-membered partially saturated fused ring system containing carbon ring members and 2 nitrogen ring members, the ring substituted with 1 substituent selected from R 22 on one nitrogen ring member.
  • Embodiment 53D A compound of Embodiment 53C wherein each G A is
  • bond projecting to the left represents the point of attachment to the remainder of the compound of Formula 1.
  • Embodiment 53E A compound of Embodiment 53D wherein each G A is
  • Embodiment 54 A compound of Formula 1 or any one of Embodiments 1 through 53E wherein R 2 is phenyl or -W 3 (phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G; or C 1 -Cg alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -CJ0 cycloalkylalkyl, Cg-C ⁇ cycloalkylcycloalkyl, C 4 -C 10
  • halocycloalkylalkyl C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C alkoxyalkyl, C 3 -CK ) alkoxyalkenyl, C 4 -C 10 cycloalkoxyalkyl, C 4 -C 10 cycloalkoxylalkoxyalkyl, C 3 -C J0 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -Cg alkylsulfinylalkyl, C 2 -C ⁇ alkylsulfonylalkyl, C 2 -Cg alkylcarbonyl, C 4 -C 10 cycloalkenylalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkoxyhaloalkyl,
  • haloalkylsulfinyl C 1 -Cg alkylsulfonyl, C 1 -Cg haloalkylsulfonyl, C 3 -C cycloalkylsulfonyl, C 3 -C 8 trialkylsilyl, C 3 -C 8 cycloalkenyloxy, C 3 -Cg halocycloalkenyloxy, C 2 -Cg haloalkoxyalkoxy, C 2 -Cg alkoxyhaloalkoxy, C 2 -C 8 haloalkoxyhaloalkoxy, C 3 -C J0 alkoxycarbonylalkoxy, C 2 -Cg
  • alkyl(thiocarbonyl)oxy C 3 -Cg cycloalkylsulfinyl or C 3 -C 10 halotrialkylsilyl; or
  • Embodiment 54 A A compound of Embodiment 54 wherein R 2 is phenyl or
  • Embodiment 59 A compound of Formula 1 or any one of Embodiments 1 through 58 wherein each E 4 , E 5 and E 6 is independently O, NOR 37 or N(R 37 )2.
  • Embodiment 60 A compound of Formula 1 or any one of Embodiments 1 through 56 wherein E 4 is O.
  • Embodiment 61 A compound of Formula 1 or any one of Embodiments 1 through 56 wherein E 4 is NOR 37 .
  • Embodiment 62 A compound of Embodiment Formula 1 or any one of Embodiments
  • E 4 is NN(R 37 ) 2 .
  • Embodiment 63 A compound of Formula 1 or any one of Embodiments 1 through 55 or 57 wherein E 5 is O.
  • Embodiment 64 A compound of Formula 1 or any one of Embodiments 1 through 55 or 57 wherein E 5 is NOR 37 .
  • Embodiment 65 A compound of Formula 1 or any one of Embodiments 1 through 55 or 57 wherein E 5 is NN(R 37 ) 2 .
  • Embodiment 66 A compound of Formula 1 or any one of Embodiments 1 through 55 or 58 wherein E 6 is O.
  • Embodiment 67 A compound of Formula 1 or any one of Embodiments 1 through 55 or 58 wherein E 6 is NOR 37 .
  • Embodiment 68 A compound of Formula 1 or any one of Embodiments 1 through 55 or 58 wherein E6 is NN(R 37 ) 2 .
  • Embodiment 68 A A compound of Formula 1 or any one of Embodiments 1 through 68 wherein W 6 is C 2 -C 4 alkylene, -(CH 2 ) 2 OCH 2 - or -(CH 2 ) 3 OCH 2 -.
  • Embodiment 69 A compound of Formula 1 or any one of Embodiments 1 through 68 wherein W 6 is C 2 -C 4 alkylene.
  • Embodiment 70 A compound of Formula 1 or any one of Embodiments 1 through 55 or 57 through 59 or 63 through 69 wherein each L 1 is independently O or N(R 8).
  • Embodiment 70A A compound of any one of Embodiments 59, 61, 64 through 65 or 68 wherein each R 37 is independently H, C1-C 3 alkyl or C1-C 3 haloalkyl.
  • Embodiment 71 A compound of Formula 1 or any one of Embodiments 1 through 70 wherein each R 33 , R 34 and R 35 is independently hydrogen; or C 1 -C 6 alkyl or C 3 -C 6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO2, hydroxy, CJ-C 4 alkoxy, C 1 -C 4 alkylsulfinyl and CJ-C 4 alkylsulfonyl.
  • Embodiment 7 IB A compound of Embodiment 71 wherein each R 33 , R 34 and R 35 is independently hydrogen; or C1-C 4 alkyl, C 3 -C5 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, hydroxy, C1-C 2 alkoxy, C1-C 2 alkylsulfinyl and C1-C 2
  • Embodiment 72 A compound of Embodiment 7 IB wherein each R 33 , R 34 and R 35 is independently hydrogen; or C J-C 2 alkyl or C 3 -C 4 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, hydroxy and C J-C 2 alkoxy.
  • Embodiment 73 A compound of Formula 1 or any one of Embodiments 1 through 72 wherein R 2 is phenyl or -W 3 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or -G; or C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl.
  • Embodiment 74 A compound of Embodiment 73 wherein R 2 is phenyl optionally substituted on ring members with up to two substituents selected from R 21 ; or
  • Embodiment 74 A A compound of Embodiment 73 wherein R 2 is phenyl; or -G; or C 3 -C 8 cycloalkyl.
  • Embodiment 74B A compound of Embodiment 74A wherein R 2 is phenyl, 2-thienyl
  • Embodiment 74C A compound of Embodiment 74A wherein R 2 is phenyl, 3-thienyl or cyclopropropyl.
  • Embodiment 75 A compound of Embodiment 74 wherein R 2 is phenyl,
  • Embodiment 76 A compound of Embodiment 74 wherein R 2 is phenyl,
  • Embodiment 76A A compound of Embodiment 74A wherein R 2 is 5-chloro-2- pyridinyl.
  • Embodiment 77 A compound of Embodiment 74 wherein R 2 is phenyl.
  • Embodiment 78 A compound of Formula 1 or any one of Embodiments 1 through 76 wherein R 2 is other than phenyl.
  • Embodiment 79 A compound of Embodiment 74 wherein R 2 is 3-thienyl, 2-thienyl or
  • Embodiment 79A A compound of Embodiment 79 wherein R 2 is 2-thienyl.
  • Embodiment 80 A compound of Embodiment 79 wherein R 2 is 3-pyridinyl.
  • Embodiment 81 A compound of Embodiment 76 wherein R 2 is w-propyl, «-butyl or cyclopropyl.
  • Embodiment 81 A A compound of Embodiment 81 wherein R 2 is cyclopropyl.
  • Embodiment 82 A compound of Formula 1 or any one of Embodiments 1 through 75 wherein W 3 is -CH2-.
  • Embodiment 83 A compound of Formula 1 or any one of Embodiments 1 through 75 wherein W 4 is -CH 2 -.
  • Embodiment 84 A compound of Formula 1 or any one of Embodiments 1 through 83 wherein R 3 is hydroxy, -OM + , C 2 -C alkylcarbonyloxy, C 2 -Cg
  • alkylcarbonylalkoxy or benzyloxy, phenyloxy, benzylcarbonyloxy,
  • Embodiment 85 A compound of Embodiment 84 wherein R 3 is hydroxy, -0 ⁇ M + or C 2 -Cg alkylcarbonyloxy; or phenylsulfonyloxy optionally substituted with up to two substituents selected from R 21 .
  • Embodiment 86 A compound of Embodiment 85 wherein M + is a sodium or
  • Embodiment 87 A compound of Embodiment 86 wherein R 3 is hydroxy or C 2 -Cg alkylcarbonyloxy.
  • Embodiment 88 A compound of Embodiment 87 wherein R 3 is hydroxy or
  • Embodiment 89 A compound of Formula 1 or any one of Embodiments 1, 7 and 14 through 88 wherein R 4 , R 5 , R 6 and R 7 are each independently H or C 1 -C alkyl.
  • Embodiment 90 A compound of Formula 1 or any one of Embodiments 1 or 7
  • R 8 is C 1 -Cg alkyl or C 3 -Cg cycloalkyl.
  • Embodiment 91 A compound of Embodiment 90 wherein R 8 is CH3, CH2CH3 or cyclopropyl.
  • Embodiment 92 A compound of Formula 1 or any one of Embodiments 1 through 3 or
  • R 9 is C 1 -Cg alkyl.
  • Embodiment 93 A compound of Embodiment 92 wherein R 9 is CH2CH3.
  • Embodiment 94 A compound of Formula 1 or any one of Embodiments 1 through 3 or 14 through 93 wherein R 10 is H, halogen or C 1 -Cg alkyl.
  • Embodiment 95 A compound of Embodiment 94 wherein R 10 is H or CH3.
  • Embodiment 96 A compound of Formula 1 or any one of Embodiments 1, 2 or 14 through 95 wherein R 11 is H or C 1 -C 6 alkyl.
  • Embodiment 97 A compound of Embodiment 96 wherein R 1 1 is H.
  • Embodiment 98 A compound of Formula 1 or any one of Embodiments 1, 2 or 14 through 97 wherein R 12 is H, halogen, cyano, hydroxy, amino or C 1 -C 6 alkyl.
  • Embodiment 99 A compound of Embodiment 98 wherein R 12 is H, halogen, cyano, C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl.
  • Embodiment 100 A compound of Embodiment 99 wherein R 12 is CH3, CH2CH3 or cyclopropyl.
  • Embodiment 101 A compound of Formula 1 or any one of Embodiments 1 or 14 through 100 wherein R 13 is H, halogen, cyano or nitro.
  • Embodiment 102 A compound of Embodiment 101 wherein R 13 is cyano or nitro.
  • Embodiment 103 A compound of Formula 1 or any one of Embodiments 1 through
  • R 14 and R 18 are taken alone (i.e. R 14 and R 18 are not taken together as alkylene or alkenylene), then independently said instances of R 14 and R 18 are H or C 1 -C 6 alkyl.
  • Embodiment 104 A compound of Embodiment 103 wherein when instances of R 14 and R 18 are taken alone, then independently said instances of R 14 and R 18 are H or CH 3 .
  • Embodiment 105 A compound of Embodiment 104 wherein when instances of R 14 and R 18 are taken alone, then independently said instances of R 14 and R 18 are H.
  • Embodiment 106 A compound of Formula 1 or any one of Embodiments 1 through
  • Embodiment 107 A compound of Formula 1 or any one of Embodiments 1 through
  • Embodiment 108 A compound of Formula 1 or any one of Embodiments 1 through
  • each R 15 and R 19 is H or C 1 -Cg alkyl.
  • Embodiment 109 A compound of Embodiment 108 wherein independently each R 15 and R 19 is H or CH 3 .
  • Embodiment 110 A compound of Embodiment 109 wherein independently each R 15 and R 19 is H.
  • Embodiment 110A A compound of any one of Embodiments 104 and 109 wherein each R 14 , R 15 , R 18 and R 19 is H or CH 3 .
  • Embodiment 110B A compound of Embodiment 110A wherein each R 14 , R 15 , R 18 and R 19 is H.
  • Embodiment 111 A compound of Formula 1 or any one of Embodiments 1 through
  • R 2 ° is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 3 -C 8 cycloalkyl.
  • Embodiment 112 A compound of Embodiment 111 wherein R 20 is H or CH 3 .
  • Embodiment 114 A compound of Embodiment 113 wherein T is -CH 2 CH 2 -.
  • Embodiment 115 A compound of Formula 1 or any one of Embodiments 1 through 54, 75 or 84 through 114 wherein each G is independently a 5- or 6-membered heterocyclic ring optionally substituted with up to five substituents selected from R 21 on carbon ring members and R 22 on nitrogen ring members.
  • Embodiment 116 A compound of Embodiment 115 wherein G is
  • r is 0, 1, 2 or 3.
  • Embodiment 117 A compound of Embodiment 116 wherein G is G-2, G-3 or G-15.
  • Embodiment 119 A compound of Embodiment 118 wherein G is G-2.
  • Embodiment 120 A compound of Embodiment 118 wherein G is G-3.
  • Embodiment 120A A compound of Embodiment 116 wherein G is G-15.
  • Embodiment 121. A compound of Formula 1 or any one of Embodiments 1 through 120 wherein each R 21 is independently halogen, cyano, hydroxy, nitro, -CHO, -SH, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -Cg haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -CJ Q alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -Cg alkoxyalkyl,
  • cycloalkylalkoxy C 2 -C 6 alkenyloxy, C 2 -Cg haloalkenyloxy, C 2 -Cg alkoxyalkoxy, C 2 -Cg alkylcarbonyloxy, C 1 -Cg alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C Cg alkylsulfinyl, C 1 -Cg haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C ⁇ -C 6 haloalkylsulfonyl or C 3 -C 8 cycloalkylsulfonyl.
  • Embodiment 121 A A compound of Embodiment 121 wherein each R 21 is
  • Embodiment 122 A compound of Embodiment 121 A wherein each R 21 is
  • Embodiment 123 A compound of Formula 1 or any one of Embodiments 1 through 122 wherein each R 22 is independently C Cg alkyl or C 1 -C 6 haloalkyl.
  • Embodiment 124 A compound of Embodiment 123 wherein each R 22 is
  • Embodiment 124A A compound of Embodiment 124 wherein R 22 is CH3.
  • Embodiment 124B A compound of Formula 1 or any one of Embodiments 1 through 124A wherein R 40 is ethyl or z ' -propyl.
  • Embodiment 124C A compound of Fromula 1 or any one of Embodiments 1 through 124A wherein R 41 is ethyl or z ' -propyl.
  • Embodiment 124E A compound of Embodiment 124D wherein R 40 and R 41 are taken together as -(CH 2 ) 5 - or -(CH 2 ) 2 0(CH 2 ) 2 -.
  • Embodiment 124F A compound of Embodiment 124E wherein R 40 and R 41 are taken together as -(CH 2 ) 2 0(CH 2 ) 2 -.
  • This invention also includes a herbicidal mixture comprising (a) a compound selected from Formula 1, N-oxides, and salts thereof, and (b) at least one additional active ingredient selected from (bl) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5) 5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6) photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors, (blO) auxin transport inhibitors, (bl l) phytoene desaturase (PDS) inhibitors, (bl2) 4-hydroxyphenyl -pyruv
  • Embodiment 125 A herbicidal mixture comprising (a) a compound of Formula 1 or any one of Embodiments 1 through 125E, and (b) at least one additional active ingredient selected from (bl), (b2), (b3), (bl2), (bl3) and (bl5).
  • Embodiment 126 A herbicidal mixture of Embodiment 125 wherein component (b) comprises at least one additional active ingredient selected from (bl), (bl2),
  • Embodiment 127 A herbicidal mixture of Embodiment 126 wherein component (b) comprises at least one additional active ingredient selected from (bl).
  • Embodiment 128 A herbicidal mixture of Embodiment 127 wherein component (b) comprises bromoxynil.
  • Embodiment 129 A herbicidal mixture of Embodiment 127 wherein component (b) comprises dimethametryn.
  • Embodiment 130 A herbicidal mixture of Embodiment 126 wherein component (b) comprises at least one additional active ingredient selected from (bl3).
  • Embodiment 131 A herbicidal mixture of Embodiment 130 wherein component (b) comprises haloxydine.
  • Embodiment 132 A herbicidal mixture of Embodiment 126 wherein component (b) comprises at least one additional active ingredient selected from (bl5).
  • Embodiment 133 A herbicidal mixture of Embodiment 132 wherein component (b) comprises at least one additional active ingredient selected from allidochlor, benoxacor, 1 -bromo-4-[(chloromethyl)sulfonyl]benzene, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, 4-(dichloroacetyl)-l-oxa-4-azospiro[4.5]decane (MON 4660),
  • component (b) comprises at least one additional active ingredient selected from allidochlor, benoxacor, 1 -bromo-4-[(chloromethyl)sulfonyl]benzene, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, 4-
  • Embodiment 134 A herbicidal mixture of Embodiment 133 wherein component (b) comprises at least one additional active ingredient selected from benoxacor, cloquintocet-mexyl, cyprosulfamide, diamuron, fenchlorazole-ethyl, mefenpyr-diethyl, mephenate and oxabetrinil.
  • component (b) comprises at least one additional active ingredient selected from benoxacor, cloquintocet-mexyl, cyprosulfamide, diamuron, fenchlorazole-ethyl, mefenpyr-diethyl, mephenate and oxabetrinil.
  • Embodiment 135. A herbicidal mixture of Embodiment 134 wherein component (b) comprises at least one additional active ingredient selected from
  • Embodiment 136 A herbicidal mixture of Embodiment 135 wherein component (b) comprises at least one additional active ingredient selected from
  • Embodiment 137 A herbicidal mixture of Embodiment 135 wherein component (b) comprises at least one additional active ingredient selected from oxabetrinil.
  • Embodiments of this invention can be combined in any manner, and the descriptions of variables in the embodiments pertain not only to the compounds of Formula 1 but also to the starting compounds and intermediate compounds, including compounds of Formulae 1Q, 1R and IS, useful for preparing the compounds of Formula 1.
  • embodiments of this invention including Embodiments 1-124E or 125—137 above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present invention.
  • Embodiment A A compound of Formula 1 wherein
  • A is A-l, A-3, A-4, A-5 or A-6;
  • R 1 is N(R 40 )R 41 ;
  • R 1 is G A or -W 2 G A ;
  • G A is a 9- to 11-membered saturated or partially saturated carbospirocyclic or
  • each G A is a 9-membered partially saturated fused ring system containing carbon ring members and 2 nitrogen ring members, the ring substituted with 1 substituent selected from R 22 on one nitrogen ring member;
  • each E 1 , E 2 and E 3 is independently O, NOR 28 or N(R 28 ) 2 ;
  • L is independently O or N(R 31 );
  • each R 24 , R 25 and R 26 is independently hydrogen; or C1-C 4 alkyl or C 3 -C 5 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, hydroxy, ⁇ -0 2 alkoxy, C 1 -C 2 alkylsulfinyl and
  • each R 28 is independently H, C1-C 3 alkyl or C1-C 3 haloalkyl;
  • each R 29 is independently H, C1-C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkylcarbonyl,
  • each Q 1 and Q 2 is independently O or N(R 31 );
  • Q 3 is C 2 -C 3 alkylene optionally substituted with up to 2 substituents selected from
  • R 30 is independently H, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl
  • R 31 is independently H, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl
  • R 3 is H or C r C 3 alkyl
  • W 1 is C 2 -C 4 alkylene, -(CH 2 ) 2 OCH 2 - or -(CH 2 ) 3 OCH 2 -;
  • W 2 is C r C 3 alkylene
  • W 5 is C 1-C 4 alkylene
  • R 2 is phenyl or -W 3 (phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -Cg halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10
  • cycloalkylalkyl C5-CJ4 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C5"C 12 alkylcycloalkylalkyl, C 3 -Cg cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -Cg alkoxyalkyl, C 3 -C 10 alkoxyalkenyl, C 4 -C 10 cycloalkoxyalkyl, C 4 -C 10 cycloalkoxylalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -Cg alkylthioalkyl, C 2 -Cg alkylsulfinylalkyl, C 2 -C 8 alkylsulfonylalkyl, C 2 -Cg alkylcarbonyl, C 4 -C 10 cycloalkenylalkyl, C
  • cycloalkenyloxyalkyl C 4 -CJ Q halocycloalkenyloxyalkyl, C 3 -C 10 dialkoxyalkyl, C 1 -Cg alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 3 -C5 alkynyloxy, C 3 -C 6 haloalkynyloxy, C 2 -C alkoxyalkoxy, C 2 -Cg
  • alkylcarbonyloxy C 2 -C 8 haloalkylcarbonyloxy, C 4 -C 10 cycloalkylcarbonyloxy, C 3 -C 10 alkylcarbonylalkoxy, C 1 -Cg alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -Cg alkylsulfinyl, C 1 -Cg haloalkylsulfinyl, C 1 -Cg
  • alkylsulfonyl C ⁇ -Cg haloalkylsulfonyl, C 3 -Cg cycloalkylsulfonyl, C 3 -Cg trialkylsilyl, C 3 -C 8 cycloalkenyloxy, C 3 -C halocycloalkenyloxy, C 2 -Cg haloalkoxyalkoxy, C 2 -Cg alkoxyhaloalkoxy, C 2 -Cg haloalkoxyhaloalkoxy, C 3 -C 10 alkoxycarbonylalkoxy, C 2 -Cg alkyl(thiocarbonyl)oxy, C 3 -C
  • each E 4 , E 5 , and E 6 is independently O, NOR 37 or NN(R 37 ) 2 ;
  • each L 1 is independently O or N(R 8 );
  • each R 33 , R 34 and R 35 is independently hydrogen; or C1-C 4 alkyl, C 3 -C5 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, hydroxy, C 1 -C 2 alkoxy, C C 2 alkylsulfinyl and C 1 -C 2 alkylsulfonyl;
  • each R 37 is independently H, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl;
  • R 38 is independently H, C 1 -C 3 alkyl or C 1 -C 3 haloalkyl
  • W 3 is -CH 2 -;
  • W 6 is C 2 -C 4 alkylene, -(CH 2 ) 2 OCH 2 - or -(CH 2 ) 3 OCH 2 -;
  • R 3 is hydroxy, -OM + , C 2 -Cg alkylcarbonyloxy, C 2 -C haloalkylcarbonyloxy, C 4 -C 10 cycloalkylcarbonyloxy or C 3 -CJQ alkylcarbonylalkoxy; or benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy, phenylsulfonyloxy or benzylsulfonyloxy, each optionally substituted on ring members with up to two substituents selected from R 21 ;
  • M + is a sodium or potassium metal cation
  • R 9 is C 1 -C 6 alkyl
  • R 10 is H, halogen or C 1 -C 6 alkyl
  • R 1 1 is H or C 1 -C 6 alkyl
  • R 12 is H, halogen, cyano, hydroxy, amino or C 1 -Cg alkyl
  • each R 14 , R 15 , R 18 and R 19 is H or CH 3 ;
  • R 20 is H or CH 3 ;
  • each G is G-l through G-20 (as depicted in Embodiment 116);
  • r 0, 1, 2 or 3;
  • each R 21 is independently halogen, cyano, hydroxy, nitro, -CHO, -SH, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C r C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -Cg cycloalkyl, C 3 -Cg halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -CJ Q cycloalkylalkyl, C 3 -Cg cycloalkenyl, C 3 -Cg halocycloalkenyl, C 2 -C alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C j0 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2
  • alkylcarbonyloxy C 1 -C alkylthio, C 1 -Cg haloalkylthio, C 3 -C cycloalkylthio, C 1 -Cg alkylsulfinyl, C 1 -Cg haloalkylsulfinyl, C 1 -Cg alkylsulfonyl, C 1 -Cg haloalkylsulfonyl or C 3 -C cycloalkylsulfonyl;
  • each R 22 is independently C 1 -Cg alkyl or C 1 -Cg haloalkyl
  • R 40 is ethyl or /-propyl
  • R 41 is ethyl or z ' -propyl
  • Embodiment B A compound of Embodiment A wherein
  • A is A-l, A-3 or A-5;
  • B 1 is C-l
  • B 2 is C-3;
  • B 3 is C-l
  • R 1 is -G A ;
  • each G A is selected from G A -1, G A -2, G A -3, G A -7, G A -8 and G A -9; or
  • R 2 is phenyl or -W 3 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or -G; or C 1 -Cg alkyl or C 3 -C cycloalkyl; R 3 is hydroxy or C 2 -C alkylcarbonyloxy;
  • R 9 is CH 2 CH 3 ;
  • R 10 is H or CH 3 ;
  • T is -CH 2 CH 2 -;
  • G is G-2, G-3 or G- 15;
  • R 1 is independently halogen, nitro, C 1 -Cg alkyl, C 1 -Cg haloalkyl, C 1 -Cg alkoxy, C 1 -Cg haloalkoxy or C 1 -Cg alkylthio;
  • each R 22 is independently CH 3 or CH 2 CF 3 ;
  • Embodiment C A compound of Embodiment B wherein A is A-l or A-3;
  • each G A is selected from G A -2 and G A -3; or
  • R 2 is phenyl; or -G; or C 3 -C 8 cycloalkyl
  • R 40 and R 41 are taken together as -(CH 2 ) 5 - or -(CH 2 )20(CH 2 )2-.
  • Embodiment D A compound of Embodiment C wherein
  • A is A-l
  • R 2 is phenyl
  • R 30 is H or methyl
  • R 21 halogen or C 1-C 3 alkyl
  • R 22 is CH 3 .
  • Embodiment E A compound of Embodiment B wherein
  • A is A-l
  • G A is G A -2;
  • R 2 is phenyl, 2-thienyl, 5-chloro-2-pyridinyl or cyclopropyl; R 3 is hydroxy; and
  • each R 14 , R 15 , R 18 and R 19 is H.
  • Embodiment F A compound of Embodiment B wherein
  • A is A-3;
  • G A is G A -2;
  • R 2 is phenyl, 2-thienyl 5-chloro-2-pyridinyl or cyclopropyl; and R 3 is hydroxy.
  • Embodiment G A compound of Embodiment A wherein
  • A is A-l
  • each Q 1 and Q 2 is O;
  • Q 3 is C 2 -alkylene;
  • R 32 is H or methyl
  • W 5 is C 2 -C 3 alkylene
  • R 2 is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl,
  • each R 14 , R ⁇ , Rl8 and R 19 is H or CH 3 .
  • Embodiment H A compound of Embodiment G wherein
  • W 5 is C 2 alkylene or C 3 alkylene
  • R 2 is phenyl, 3-thienyl cyclopropropyl
  • R 3 is hydroxy
  • Specific embodiments include a compound of Formula 1 selected from:
  • Embodiments of the present invention as described in the Summary of the Invention also include (where Formula 1Q from the Summary of the Invention as used in the following Embodiments includes N-oxides and salts thereof):
  • Embodiment 1Q A compound of Formula 1Q wherein A' is A'-l, A'-3 or A'-5.
  • Embodiment 2Q A compound of Embodiment 1Q wherein A' is A'-l or A'-3.
  • Embodiment 3Q A compound of Embodiment 2Q wherein A' is A'-l.
  • Embodiment 4Q A compound of Embodiment 2Q wherein A' is A'-3.
  • Embodiment 5Q A compound of Formula 1Q or any one of Embodiments 1Q through
  • Embodiment 6Q A compound of Formula 1Q or any one of Embodiments 1Q through
  • Embodiment 7Q A compound of Formula 1Q or any one of Embodiments 1Q through
  • Embodiment 8Q A compound of Formula 1Q or any one of Embodiments 1Q through
  • Embodiment 9Q A compound of Formula 1Q or any one of Embodiments 1Q through
  • Embodiment 10Q A compound of Formula 1Q or any one of Embodiments 1Q
  • Embodiment 11Q A compound of Formula 1Q or any one of Embodiments 1Q
  • R 1 is -G A or -W 2 G A .
  • Embodiment 12Q A compound of Formula 1Q or any one of Embodiments 1Q
  • Embodiment 13Q A compound of Embodiment 12Q wherein each Q 1 and Q 2 is O.
  • Embodiment 14Q A compound of Embodiment 12Q wherein Q 3 is C 2 -alkylene optionally substituted with up to 2 substituents selected from C j-C 2 alkyl.
  • Embodiment 15Q A compound of Embodiment 14Q wherein Q 3 is C 2 -alkylene optionally substituted with up to 2 substituents selected from methyl.
  • Embodiment 16Q A compound of Formula 1Q or any one of Embodiments 1Q
  • W 5 is C1-C 4 alkylene.
  • Embodiment 17Q A compound of Formula 1Q or any one of Embodiments 1Q
  • R 32 is H or CJ-C 3 alkyl.
  • Embodiment 17QA A compound of Embodiment 17Q wherein R 32 is H or methyl.
  • Embodiment 18Q A compound of Embodiments 17Q wherein R 32 is methyl.
  • Embodiment 19Q A compound of Formula 1Q or any one of Embodiments 1Q
  • Embodiment 12QA A compound of Formula 1Q or any one of Embodiments 1Q through 19Q wherein W 1 is C 2 -C 4 alkylene, -(CH 2 ) 2 OCH 2 - or -(CH 2 ) 3 OCH 2 -.
  • Embodiment 20Q A compound of Formula 1Q or any one of Embodiments 1Q through 11Q or 19Q wherein each E 1 , E 2 , and E 3 is independently O, NOR 28 or NN(R 28 ) 2 .
  • Embodiment 20QA A compound of Formula 1Q or any of Embodiments 1Q through 20Q wherein each R 28 is independently H, CJ-C 3 alkyl or C1-C 3 haloalkyl
  • Embodiment 20QB A compound of Formula 1Q or any one of Embodiments 1Q through 10Q wherein R 1 is other than -N(R 40 )(R 41 ).
  • Embodiment 21 Q A compound of Formula 1Q or any one of Embodiments 1Q
  • each L is independently O or N(R 3 ! );
  • Embodiment 22Q A compound of Formula 1Q or any one of Embodiments 1Q
  • W 1 is CJ-C 4 alkylene.
  • Embodiment 23Q A compound of Formula 1Q or any one of Embodiments 1Q
  • each R 24 , R 25 and R 26 is independently hydrogen; or C j -C 2 alkyl or C 3 -C 4 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, hydroxyl and Ci-C 2 alkoxy.
  • Embodiment 24Q A compound of Formula 1Q or any one of Embodiments 1Q
  • Embodiment 25Q A compound of Embodiment 24Q wherein G A is a 5- or
  • Embodiment 26Q A compound of Embodiment 25Q wherein R 29 is independently H, C ! -C 3 alkyl, C l -C 3 haloalkyl or C 1 -C 3 alkylcarbonyl.
  • Embodiment 26QA A compound of Embodiment 25Q wherein R 30 is independently
  • Embodiment 27Q A compound of Embodiment 24Q wherein G A is a 9- to
  • Embodiment 28Q A compound of Embodiment 27Q wherein R 30 is independently H,
  • Embodiment 29Q A compound of Embodiment 27Q or 28Q wherein G A is selected from G A -1, G A -2, G A -3, G A -7, G A -8 and G A -9 (as described in Embodiment Embodiment 30Q.
  • G A is selected from G A -2 and G A -3.
  • Embodiment 30QA A compound of Embodiment 30Q wherein G A is G A -2.
  • Embodiment 30QB A compound of Formula 1Q or any one of Embodiments 1Q
  • each G A is other than a 9-membered partially saturated fused ring system containing carbon ring members and 2 nitrogen ring members, the ring optionally substituted with up to 2 substituents selected from R 21 on carbon ring members and R 22 on nitrogen ring members.
  • Embodiment 30QC A compound of Formula 1 or any one of Embodiments 1Q
  • each G A is a 9-membered partially saturated fused ring system containing carbon ring members and 2 nitrogen ring members, the ring substituted with 1 substituent selected from R 22 on one nitrogen ring member.
  • Embodiment 30QD A compound of Embodiment 30QC wherein each G A is
  • bond projecting to the left represents the point of attachment to the remainder of the compound of Formula 1.
  • Embodiment 30QE A compound of Embodiment 30QD wherein each G A is
  • Embodiment 31Q A compound of Formula 1Q or any one of Embodiments 1Q
  • R 2 is phenyl or -W 3 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or -G or; or C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl.
  • Embodiment 32Q A compound of Embodiment 31Q wherein R 2 is phenyl optionally substituted on ring members with up to two substituents selected from R 21 ; or -G; or C 1 -Cg alkyl, C 3 -C 8 cycloalkyl.
  • Embodiment 32QA A compound of Embodiment 32Q wherein R 2 is phenyl; or -G; or C 3 -C 8 cycloalkyl.
  • Embodiment 32QB A compound of Embodiment 32QA wherein R 2 is phenyl,
  • Embodiment 32QC A compound of Embodiment 32QA wherein R 2 is phenyl,
  • Embodiment 33Q A compound of Embodiment 32Q wherein R 2 is phenyl,
  • Embodiment 33QA A compound of Embodiment 32Q wherein R 2 is phenyl, 3-thienyl or cyclopropropyl.
  • Embodiment 34Q A compound of Embodiment 33Q wherein R 2 is phenyl.
  • Embodiment 35Q A compound of Formula 1Q or any one of Embodiments 1Q
  • R 2 is other than phenyl.
  • Embodiment 36Q A compound of Embodiment 35Q wherein R 2 is 3-thienyl,
  • Embodiment 36Qa A compound of Embodiment 36Q wherein R 2 is 3-pyridinyl.
  • Embodiment 37Q. A compound of Formula 1Q or any one of Embodiments 1Q
  • Embodiment 38Q A compound of Formula 1Q or any one of Embodiments 1Q
  • R 9 is C 1 -C 6 alkyl.
  • Embodiment 39Q A compound of Embodiments 38Q wherein R 9 is CH2CH3.
  • Embodiment 40Q A compound of Formula 1Q or any one of Embodiments 1Q or
  • R 10 is H, halogen or C 1 -C 6 alkyl.
  • Embodiment 41Q A compound of Embodiment 40Q wherein R 10 is H or CH 3 .
  • Embodiment 42Q A compound of Formula 1Q or any one of Embodiments 1Q
  • R 14 and R 18 are taken alone (i.e. R 14 and R 18 are not taken together as alkylene or alkenylene), then independently said instances of R 14 and R 18 are H or C 1 -C 6 alkyl.
  • Embodiment 43Q A compound of Embodiment 42Q wherein when instances of R 14 and R 18 are taken alone, then independently said instances of R 14 and R 18 are H or CH 3 .
  • Embodiment 44Q A compound of Embodiment 43Q wherein when instances of R 14 and R 18 are taken alone, then independently said instances of R 14 and R 18 are H.
  • Embodiment 45Q A compound of Formula 1Q or any one of Embodiments 1Q
  • each R 15 and R 19 is H or CH3.
  • Embodiment 46Q A compound of Embodiment 45Q wherein independently each R 15 and R 19 is H.
  • Embodiment 47Q A compound of Formula 1Q or any one of Embodiments 1Q
  • Embodiment 48Q A compound of Embodiment 47Q wherein R 20 is H or CH3.
  • Embodiment 50Q A compound of Embodiment 49Q wherein T is -CH2CH2-.
  • Embodiment 51Q A compound of Formula 1Q or any one of Embodiments 1Q
  • G is G-2, G-3 or G-15 (as depicted in Embodiment 51).
  • Embodiment 52Q A compound of Embodiment 51Q wherein G is G-2 (as depicted in
  • Embodiment 53Q A compound of Embodiment 51Q wherein G is G-3 (as depicted in Embodiment 51).
  • Embodiment 54Q A compound of Formula 1Q or any one of Embodiments 1Q
  • each R 21 is independently halogen, nitro, C 1 -Cg alkyl, C 1 -Cg haloalkyl, C 1 -Cg alkoxy, C 1 -Cg haloalkoxy or C 1 -Cg alkylthio.
  • Embodiment 55Q A compound of Embodiment 54Q wherein each R 21 is
  • Embodiment 56Q A compound of Formula 1Q or any one of Embodiments 1Q
  • each R 22 is independently C 1 -C 6 alkyl or C 1 -C 6 haloalkyl.
  • Embodiment 57Q A compound of Embodiment 56Q wherein each R 22 is
  • Embodiment 58Q A compound of Formula 1Q or any one of Embodiments 1Q
  • R 40 is ethyl or /-propyl.
  • Embodiment 59Q A compound of Formula 1Q or any one of Embodiments 1Q
  • R 41 is ethyl or z-propyl.
  • Embodiment 60Q A compound of Formula 1Q or any one of Embodiments 1 through
  • Embodiment 61Q A compound of Embodiment 60Q wherein R 40 and R 1 are taken together as -(CH 2 ) 5 - or -(CH 2 ) 2 0(CH 2 ) 2 -.
  • Embodiment 62Q A compound of Embodiment 61Q wherein R 40 and R 41 are taken together as -(CH 2 ) 2 0(CH 2 ) 2 -.
  • Embodiments of the present invention as described in the Summary of the Invention also include (where Formula 1R from the Summary of the Invention as used in the following Embodiments include N-oxides and salts thereof):
  • Embodiment 1R A compound of Formula 1R wherein R 1 is
  • each Q 1 and Q 2 is O;
  • Q 3 is C 2 -alkylene
  • R 32 is H or methyl; W 5 is C 2 -C 3 alkylene;
  • R 2 is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl,
  • each R 14 , R 15 , R 18 and R 19 is H.
  • Embodiment IRA A compound of Formula 1R or Embodiment 1 wherein R 1 is other than -N(R 40 )(R 41 ).
  • Embodiment 1RB A compound of Formula 1R wherein R 2 is phenyl; or -G; or C 3 -C 8 cycloalkyl.
  • Embodiment IRC A compound of Embodiment 1RB wherein R 2 is phenyl, 2-thienyl
  • Embodiment 1RD A compound of Embodiment 1RB wherein R 2 is phenyl, 3-thienyl or cyclopropropyl.
  • Embodiment 2R A compound of Embodiment 1R wherein R 2 is phenyl,
  • Embodiment 3R A compound of Embodiment 1R wherein R 2 is phenyl, 3-thienyl or cyclopropropyl.
  • Embodiment 3RA A compound of Embodiment 1R wherein R 2 is phenyl,
  • Embodiment 4R A compound of Embodiment 1R wherein R 2 is 3-thienyl, 2-thienyl or 3-pyridinyl.
  • Embodiment 5R A compound of Embodiment 1R wherein R 2 is phenyl.
  • Embodiment 6R A compound of Formula 1R wherein
  • E 1 is NOR 28 ;
  • R 28 is H or methyl
  • R 2 is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3 -fluorophenyl 3,5-difluorophenyl, 3-thienyl, 2-thienyl or 3-pyridinyl.
  • Embodiment 7R A compound of Embodiment 6R wherein R 2 is phenyl,
  • Embodiment 8R A compound of Embodiment 6R wherein R 2 is phenyl,
  • Embodiment 9R A compound of Embodiment 6R wherein R 2 is 3-thienyl, 2-thienyl or 3-pyridinyl.
  • Embodiment 10R A compound of Embodiment 6R wherein R 2 is phenyl.
  • Embodiment 11R A compound of Formula 1R wherein
  • Rl is -G A ;
  • R 30 is H or methyl
  • R 21 halogen or C r C 3 alkyl
  • R 22 is C r C 3 alkyl.
  • Embodiment 12R A compound of Embodiment 11R wherein G A is selected from G A -1, G a -2, G a -3, G A -7, G a -8 and G A -9 (as depicted in Embodiment 51), and R 2 is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3 -fluorophenyl 3,5-difluorophenyl, 3-thienyl 2-thienyl or 3-pyridinyl;
  • Embodiment 13R A compound of Embodiment 11R wherein R 2 is phenyl,
  • Embodiment 14R A compound of Embodiment 11R wherein R 2 is phenyl,
  • Embodiment 15R A compound of Embodiment 11R wherein R 2 is 3-thienyl, 2-thienyl or 3-pyridinyl.
  • Embodiment 16R A compound of Embodiment 11R wherein R 2 phenyl.
  • Embodiment 16RA A compound of Formula 1R wherein each G A is
  • bond projecting to the left represents the point of attachment to the remainder of the compound of Formula 1R.
  • Embodiment 16RB A compound of Embodiment 16RA wherein each G A is
  • Embodiment 17R A compound of Formula 1R or any one of Embodiments 1R through 16R wherein R 40 is ethyl or /-propyl.
  • Embodiment 18R A compound of Formula 1R or any one of Embodiments 1R
  • R 41 is ethyl or /-propyl.
  • Embodiment 19R A compound of Formula 1R or any one of Embodiments 1R
  • -CH 2 CH CHCH 2 - or -(CH 2 ) 2 0(CH 2 ) .
  • Embodiment 20R A compound of Embodiment 19R wherein R 40 and R 41 are taken together as -(CH 2 ) 5 - or -(CH 2 ) 2 0(CH 2 ) 2 -.
  • Embodiment 21 R A compound of Embodiment 20R wherein R 40 and R 41 are taken together as -(CH 2 ) 2 0(CH 2 ) 2 -.
  • Embodiments of the present invention as described in the Summary of the Invention also include (where Formula IS from the Summary of the Invention as used in the following Embodiments includes N-oxides and salts thereof):
  • Embodiment IS A compound of Formula IS wherein
  • each Q 1 and Q 2 is O;
  • Q 3 is C 2 -alkylene
  • R 32 is H or methyl
  • W 5 is C 2 -C 3 alkylene
  • R 2 is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3 -fluorophenyl, 3,5-difluorophenyl, 3-thienyl, 2-thienyl or 3-pyridinyl;
  • each R 14 , R ⁇ , Rl8 and R 19 is H
  • R 23 is methyl or ethyl.
  • Embodiment ISA A compound of Formula IS or Embodiment IS wherein R 1 is other than -N(R 40 )(R 41 ).
  • Embodiment 1SB A compound of Formula IS or Embodiment IS wherein R 2 is phenyl; or -G; or C 3 -C 8 cycloalkyl.
  • Embodiment ISC A compound of Embodiment 1SB wherein R 2 is phenyl, 2-thienyl
  • Embodiment 1SD A compound of Embodiment 1SB wherein R 2 is phenyl, 3-thienyl or cyclopropropyl.
  • Embodiment 2S A compound of Embodiment IS wherein R 2 is phenyl,
  • Embodiment 2SA A compound of Embodiment IS wherein R 2 is phenyl, 3-thienyl or cyclopropropyl.
  • Embodiment 3S A compound of Embodiment IS wherein R 2 is phenyl,
  • Embodiment 4S A compound of Embodiment IS wherein R 2 is 3-thienyl, 2-thienyl or 3-pyridinyl.
  • Embodiment 5S A compound of Embodiment IS wherein R 2 is phenyl.
  • E 1 is NOR 28 ;
  • R 28 is H or methyl
  • R 2 is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl,
  • Embodiment 7S A compound of Embodiment 6S wherein R 2 is phenyl,
  • Embodiment 8S A compound of Embodiment 6S wherein R 2 is phenyl,
  • Embodiment 9S A compound of Embodiment 6S wherein R 2 is 3-thienyl, 2-thienyl or 3-pyridinyl.
  • Embodiment 9SA A compound of Embodiment 6S wherein R 2 is 2-thienyl.
  • Embodiment 10S A compound of Embodiment 6S wherein R 2 is phenyl.
  • Embodiment 1 IS. A compound of Formula IS wherein
  • R 1 is -G A ;
  • R 30 is H or methyl
  • R 21 halogen or C r C 3 alkyl
  • R 22 is C r C 3 alkyl.
  • Embodiment 12S A compound of Embodiment 1 IS wherein G A is selected from G A -1, G A -2, G A -3, G A -7, G A -8 and G A -9; and
  • R 2 is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3 -fluorophenyl, 3,5-difluorophenyl, 3-thienyl, 2-thienyl or 3-pyridinyl.
  • Embodiment 12SA A compound of Embodiment 12S wherein G A is selected from G A -2; and
  • R 2 is phenyl or 2-thienyl.
  • Embodiment 13S A compound of Embodiment 1 IS wherein wherein R 2 is phenyl,
  • Embodiment 14S A compound of Embodiment 1 IS wherein R 2 is phenyl,
  • Embodiment 15S A compound of Embodiment 1 IS wherein R 2 is 3-thienyl, 2-thienyl or 3-pyridinyl.
  • Embodiment 16S A compound of Formula IS wherein each G A is
  • bond projecting to the left represents the point of attachment to the remainder of the compound of Formula IS.
  • Embodiment 17S A compound of Embodiment 16S wherein each G A is
  • Embodiment 17SA A compound of Formula IS or any one of Embodiments IS
  • R 40 is ethyl or z ' -propyl.
  • Embodiment 18S A compound of Formula IS or any one of Embodiments IS through
  • R 41 is ethyl or z ' -propyl.
  • Embodiment 19S A compound of Formula IS or any one of Embodiments IS
  • -CH 2 CH CHCH 2 - or -(CH 2 ) 2 0(CH 2 ) 2 -.
  • Embodiment 20S A compound of Embodiment 19S wherein R 40 and R 41 are taken together as -(CH 2 ) 5 - or -(CH 2 ) 2 0(CH 2 ) 2 -.
  • Embodiment 21 S A compound of Embodiment 20S wherein R 40 and R 41 are taken together as -(CH 2 )20(CH 2 ) 2 -.
  • This invention is also directed to compounds of Formula IP (including all stereoisomers), N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides:
  • A is a radical selected from the group consisting of
  • B 1 and B 3 are each independently a radical selected from the group consisting of
  • B 2 is a radical selected from the group consisting of R 1 is
  • R 1 is -G A or -W 2 G A ;
  • each E 1 , E 2 , and E 3 is independently O, S, NR 28 , NOR 28 , NN(R 28 ) 2 , N-CN or N-N0 2 ; each L is independently O, NR 31 or S;
  • each R 24 , R 25 , R 26 and R 27 is independently hydrogen; or C 1 -Cg alkyl, C 2 -Cg alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, N0 2 , hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 alkylsulfinyl, i-C 4 alkylsulfonyl, Ci-C 4 alkylamino, C 2 -Cg dialkylamino, C 3 -C5 cycloalkylamino and (CJ-C 4 alkyl)C 3 -Cg cycloalkylamino;
  • each R 28 is independently H, C 1 -Cg alkyl or C 1 -Cg haloalkyl;
  • R 29 is independently H, C 1 -Cg alkyl, C C haloalkyl, C 1 -Cg alkylcarbonyl, C 1 -Cg alkylsulfonyl, or C 1 -C haloalkylsulfonyl;
  • each Q 1 and Q 2 is independently O, S or -NR 31 ;
  • Q 3 is C j -C 4 alkylene optionally substituted with up to 4 substituents selected from C 1 -Cg alkyl, C 2 -Cg alkenyl, C 2 -Cg alkynyl and C 3 -C 6 cycloalkyl;
  • R 30 is independently H, C 1 -Cg alkyl or C 1 -Cg haloalkyl
  • R 31 is independently H, C 1 -Cg alkyl or C 1 -Cg haloalkyl
  • R 32 is H or C 1 -C 6 alkyl
  • each x is 0, 1 or 2;
  • W 5 is C 1 -C 6 alkylene
  • W 1 is C 1 -Cg alkylene, C 2 -C 6 alkenylene or C 2 -Cg alkynylene; or -(CH 2 ) 2 OCH 2 - or -(CH 2 ) 3 OCH 2 -;
  • cycloalkylalkyl Cg-C ⁇ cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -Cg alkoxyalkyl, C 3 -C 10 alkoxyalkenyl, C 4 -CJQ cycloalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -Cg alkylthioalkyl, C 2 -Cg alkylsulfinylalkyl, C 2 -C 8 alkylsulfonylalkyl, C 2 -C 8 alkylaminoalkyl, C 3 -C 10 dialkylaminoalkyl, C 2 -Cg haloalkylaminoalkyl, C
  • cycloalkylaminocarbonyl C 2 -C 5 cyanoalkyl, C 1 -Cg hydroxyalkyl, C ⁇ -CIQ cycloalkenylalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -Cg alkoxyhaloalkyl, C 2 -Cg haloalkoxyhaloalkyl, C 4 -C 10 halocycloalkoxyalkyl, C 4 -C 10
  • cycloalkenyloxyalkyl C 4 -CJ Q halocycloalkenyloxyalkyl, C 3 -C 10 dialkoxyalkyl, C 3 -C 10 alkoxyalkylcarbonyl, C 3 -C 10 alkoxycarbonylalkyl, C 2 -C 8
  • haloalkoxycarbonyl C 1 -C 6 alkoxy, C 1 -Cg haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -Cg haloalkenyloxy, C 2 -Cg alkynyloxy, C 3 -C5 haloalkynyloxy, C 2 -Cg alkoxyalkoxy, C 2 -C 8 alkylcarbonyloxy, C 2 -C 8 haloalkylcarbonyloxy, C 4 -C 10
  • cycloalkylcarbonyloxy C 3 -C 10 alkylcarbonylalkoxy, C 1 -C 6 alkylthio, C 1 -Cg haloalkylthio, C 3 -Cg cycloalkylthio, C 1 -Cg alkylsulfinyl, C 1 -Cg
  • haloalkylsulfinyl C 1 -Cg alkylsulfonyl, C 1 -Cg haloalkylsulfonyl, C 3 -Cg cycloalkylsulfonyl, C 3 -Cg trialkylsilyl, C 3 -Cg cycloalkenyloxy, C 3 -C 8 halocycloalkenyloxy, C 2 -Cg haloalkoxyalkoxy, C 2 -C 8 alkoxyhaloalkoxy, C 2 -Cg haloalkoxyhaloalkoxy, C 3 -C 10 alkoxycarbonylalkoxy, C 2 -C 8
  • alkyl(thiocarbonyl)oxy C 2 -C ⁇ alkylcarbonylthio, C 2 -C 8 alkyl(thiocarbonyl)thio, C 3 -Cg cycloalkylsulfinyl, C 1 -Cg alkylaminosulfonyl, C 2 -Cg
  • each E 4 , E 5 , and E 6 is independently O, S, NR 37 , NOR 37 , NN(R 37 ) 2 , N-CN or N-N0 2 ; each L 1 is independently O, NR 38 or S;
  • each R 33 , R 34 , R 35 and R 36 is independently hydrogen; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -Cg alkynyl or C 3 -C 6 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, N0 2 , hydroxy,
  • each R 37 is independently H, C 1 -Cg alkyl or C 1 -Cg haloalkyl;
  • each Q 4 and Q 5 is independently O, S or NR 38 ;
  • Q 6 is C1-C 4 alkylene optionally substituted with up to 4 substituents selected from C 1 -Cg alkyl, C 2 -Cg alkenyl, C 2 -Cg alkynyl and C 3 -C 6 cycloalkyl;
  • R 38 is independently H, C 1 -Cg alkyl or C 1 -Cg haloalkyl
  • R59 is H or C 1 -C 6 alkyl
  • each x is 0, 1 or 2;
  • W 7 is C 1 -C 6 alkylene
  • W 6 is C 1 -C 6 alkylene, C 2 -C 6 alkenylene or C 2 -C 6 alkynylene; or -(CH 2 ) 2 OCH 2 - or
  • W 3 is C Cg alkylene, C 2 -C 6 alkenylene or C 2 -Cg alkynylene;
  • W 4 is C 1 -C 6 alkylene
  • alkylcarbonylalkoxy C 1 -Cg alkylthio, C 1 -Cg haloalkylthio, C 3 -Cg
  • alkylsulfonyl C 1 -Cg haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 1 -Cg alkylsulfonyloxy, C 1 -Cg alkylamino, C 2 -Cg dialkylamino, C 1 -Cg
  • haloalkylamino C 2 -Cg halodialkylamino, C 3 -C 8 cycloalkylamino, C 2 -Cg alkylcarbonylamino, C 2 -C 8 haloalkylcarbonylamino, C 1 -C 6 alkylsulfonylamino or C 1 -Cg haloalkylsulfonylamino; or benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy, phenyl sulfonyloxy, benzylsulfonyloxy, phenylthio, benzylthio, phenylsulfinyl, benzylsulfinyl, phenylsulfonyl or benzylsulfonyl, each optionally substituted on ring members with up to five substituents selected from R 21 ;
  • M + is an alkali metal cation or an ammonium cation
  • R 4 , R 5 , R 6 and R 7 are each independently H, halogen, hydroxy, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -Cg haloalkyl, C 1 -Cg alkoxy, C 1 -Cg haloalkoxy, C 3 -C 8 cycloalkoxy or C 3 -C 8 halocycloalkoxy; or phenyl or benzyl, each optionally substituted on ring members with up to five substituents selected from R21;
  • R 8 is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6
  • haloalkenyl C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl or C 3 -C 8 halocycloalkyl; or benzyl optionally substituted on ring members with up to five substituents selected from R 21 ;
  • R 9 is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 2 -C 6
  • haloalkenyl C 2 -Cg haloalkynyl, C 3 -Cg cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C ⁇ cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 22 alkylcycloalkylalkyl, C 3 -Cg cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -Cg alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl or C 2 -Cg alkylthioalkyl;
  • R 10 is H, halogen, cyano, hydroxy, amino, nitro, SH, -S0 2 NH 2 , -S0 2 NHCN,
  • R 1 1 is H, halogen, cyano, hydroxy, amino, C 1 -Cg alkyl, C 2 -C 8 alkenyl, C 2 -C 6 alkynyl, C 1 -Cg haloalkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 haloalkynyl, C 3 -Cg cycloalkyl, C 3 -C halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -Cg halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 10 al
  • R 12 is H, halogen, cyano, hydroxy, amino, C 1 -Cg alkyl, C 2 -C alkenyl, C 2 -C 6 alkynyl, C 1 -Cg haloalkyl, C 2 -Cg haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C -C ⁇ cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C5-C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl or C 2 -Cg alkoxycarbonylamino;
  • R 13 is H, halogen, cyano, hydroxy, amino, nitro or C 2 -C 8 alkoxycarbonyl
  • n 0, 1, or 2;
  • each R 14 , R 15 , R 18 and R 19 is independently H, halogen, cyano, hydroxy or C 1 -Cg alkyl; or
  • R 14 and R 18 is taken together as C 2 -Cg alkylene or C 2 -Cg alkenylene;
  • R 20 is H, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 1 -Cg alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 8 cycloalkyl; T is C 1 -Cg alkylene or C 2 -C alkenylene;
  • each G is independently a 5- or 6-membered heterocyclic ring or an 8-, 9- or
  • cycloalkylalkyl C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -Cg alkylsulfinylalkyl, C 2 -Cg alkoxyhaloalkyl, C 2 -C5 cyanoalkyl, C 1 -Cg hydroxyalkyl, C 1 -Cg alkoxy, C 1 -Cg haloalkoxy, C 3 -Cg cycloalkoxy, C 3 ⁇ Cg halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C alkenyloxy, C 2 -C haloalkenyloxy, C 2 -
  • each R 22 is independently C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C3 ⁇ 4 alkynyl, C 1
  • haloalkyl C 3 -C 8 cycloalkyl or C 2 -Cg alkoxyalkyl.
  • Embodiment PA is A-l, A-3, A-4, A-5 or A-6;
  • Rl is G A or -W G A ;
  • L is independently O or NR 31 ;
  • each R 24 , R 25 and R 26 is independently hydrogen; or C1-C 4 alkyl or C 3 -C5 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, hydroxy, i-C 2 alkoxy, C 1 -C 2 alkylsulfinyl and C1-C 4 alkylsulfonyl;
  • each R 28 is independently H, C 1 -C 3 alkyl or CJ-C 3 haloalkyl;
  • R 29 is independently H, C C 3 alkyl, C r C 3 haloalkyl, C r C 3 alkylcarbonyl, C r C 3 alkylsulfonyl or CJ-C 3 haloalkylsulfonyl;
  • each Q 1 and Q 2 is independently O or N(R 31 );
  • Q 3 is C 2 -C 3 alkylene optionally substituted with up to 2 substituents selected from C r C 4 alkyl;
  • R 30 is independently H, C C 3 alkyl or C r C 3 haloalkyl
  • R 31 is independently H, CJ-C 3 alkyl or C1-C 3 haloalkyl
  • R 32 is H or C r C 3 alkyl
  • W 1 is C 2 -C 4 alkylene, -(CH 2 ) 2 OCH 2 - or -(CH 2 ) 3 OCH 2 -;
  • W 2 is C r C 3 alkylene
  • W 5 is C r C 4 alkylene
  • R 2 is phenyl or -W 3 (phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G; or C -C ⁇ alkyl, C 2 -C 6 alkenyl, C 2 -Cg alkynyl, C 1 -C 6 haloalkyl, C 2 -Cg haloalkenyl, C 2 -Cg haloalkynyl, C 3 -C53 cycloalkyl, C 3 -C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10
  • cycloalkylalkyl Cg-C ⁇ cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 1 2 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -Cg alkoxyalkyl, C 3 -C 10 alkoxyalkenyl, C 4 -C 10 cycloalkoxyalkyl, C 4 -C 10 cycloalkoxylalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -Cg alkylthioalkyl, C 2 -Cg alkylsulfinylalkyl, C 2 -Cg alkylsulfonylalkyl, C 2 -Cg alkylcarbonyl, C 4 -C 10 cycloalkenylalkyl
  • cycloalkenyloxyalkyl C 4 -CJ Q halocycloalkenyloxyalkyl, C 3 -C 10 dialkoxyalkyl, C 1 -Cg alkoxy, C 1 -Cg haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -Cg halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -Cg alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -Cg alkynyloxy, C 3 -C 6 haloalkynyloxy, C 2 -Cg alkoxyalkoxy, C 2 -Cg
  • alkylcarbonyloxy C 2 -Cg haloalkylcarbonyloxy, C 4 -C 10 cycloalkylcarbonyloxy, C 3 -CJ Q alkylcarbonylalkoxy, C 1 -Cg alkylthio, C 1 -C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C haloalkylsulfinyl, C 1 -C 6
  • alkylsulfonyl C 1 -Cg haloalkylsulfonyl, C 3 -Cg cycloalkylsulfonyl, C 3 -Cg trialkylsilyl, C 3 -C cycloalkenyloxy, C 3 -C halocycloalkenyloxy, C 2 -Cg haloalkoxyalkoxy, C 2 -C alkoxyhaloalkoxy, C 2 -Cg haloalkoxyhaloalkoxy, C 3 -CJ Q alkoxycarbonylalkoxy, C 2 -Cg alkyl(thiocarbonyl)oxy, C 3 ⁇ C
  • each E 4 , E 5 , and E 6 is independently O, NOR 37 or NN(R 37 ) 2 ;
  • each L 1 is independently O or NR 38 ;
  • each R 33 , R 34 and R 35 is independently hydrogen; or C j-C 4 alkyl, C 3 -C5 cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, hydroxy, Ci ⁇ C 2 alkoxy, C C 2 alkylsulfinyl, or C 1 -C 2 alkylsulfonyl;
  • each R 37 is independently H, C 1 -C 3 alkyl or C1-C 3 haloalkyl;
  • R 38 is independently H, C 1 -C 3 alkyl or haloalkyl
  • W 3 is -CH 2 -;
  • W 6 is C 2 -C 4 alkylene, -(CH 2 ) 2 OCH 2 - or -(CH 2 ) 3 OCH 2 -;
  • R 3 is hydroxy, -OM + , C 2 -Cg alkylcarbonyloxy, C 2 -Cg haloalkylcarbonyloxy, C 4 -C 10 cycloalkylcarbonyloxy or C 3 -C 10 alkylcarbonylalkoxy; or benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy, phenylsulfonyloxy or benzylsulfonyloxy, each optionally substituted on ring members with up to two substituents selected from R 21 ;
  • M + is a sodium or potassium metal cation
  • R 9 is C 1 -C 6 alkyl
  • R 10 is H, halogen or C 1 -C 6 alkyl
  • R 1 1 is H or C 1 -C 6 alkyl
  • R 12 is H, halogen, cyano, hydroxy, amino or C 1 -Cg alkyl
  • each R 14 , R 15 , R 18 and R 19 is H or CH 3 ;
  • R 20 is H or CH 3 ;
  • each G is G-l through G-20 (as depicted in Embodiment 116);
  • r 0, 1, 2 or 3;
  • each R 21 is independently halogen, cyano, hydroxy, nitro, -CHO, -SH, C 1 -Cg alkyl, C 2 -Cg alkenyl, C 2 -Cg alkynyl, C 1 -Cg haloalkyl, C 2 -Cg haloalkenyl, C 2 -Cg haloalkynyl, C 3 -Cg cycloalkyl, C 3 -Cg halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C ⁇ alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -C 10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2
  • alkylcarbonyloxy C ⁇ -Cg alkylthio, C 1 -Cg haloalkylthio, C 3 -Cg cycloalkylthio, C 1 -Cg alkylsulfinyl, C 1 -Cg haloalkylsulfinyl, C 1 -Cg alkylsulfonyl, C 1 -Cg haloalkylsulfonyl or C 3 -Cg cycloalkylsulfonyl; and
  • each R 22 is independently C 1 -Cg alkyl or C 1 -Cg haloalkyl.
  • Embodiment PB A compound of Embodiment PA wherein
  • A is A-l, A-3 or A-5;
  • Bl is C-l
  • B 2 is C-3;
  • B 3 is C-l
  • R 2 is phenyl or -W 3 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or -G; or C 1 -Cg alkyl or C 3 -Cg cycloalkyl; R 3 is hydroxy or C 2 -Cg alkylcarbonyloxy;
  • R 9 is CH 2 CH 3 ;
  • R 10 is H or CH 3 ;
  • G is G-2, G-3 or G-l 5;
  • R 21 is independently halogen, nitro, C 1 -Cg alkyl, C 1 -Cg haloalkyl, C 1 -Cg alkoxy, C 1 -Cg haloalkoxy or C 1 -Cg alkylthio.
  • Embodiment PC A compound of Embodiment PB wherein A is A-l;
  • each Q 1 and Q 2 is O;
  • Q 3 is C 2 -alkylene
  • R 32 is H or methyl
  • W 5 is C 3 -C 4 alkylene
  • R 2 is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3 -fluorophenyl 3,5-difluorophenyl, 3-thienyl or 2-thienyl;
  • each R 14 , R 15 , R 18 and R 19 is H or CH 3 .
  • Embodiment PD A compound of Embodiment B wherein
  • A is A-l
  • R 1 is -WiC ⁇ E ⁇ R 24 ;
  • E 1 is NOR 28 ;
  • R 28 is H or methyl
  • R 2 is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3 -fluorophenyl 3,5-difluorophenyl, 3-thienyl 2-thienyl or 2-pyridinyl;
  • each R 14 , R!S, RIS and R 19 is H.
  • Embodiment PE A compound of Embodiment PB wherein
  • A is A-l
  • R 1 is -G A ;
  • R 30 is R 30 is H or methyl
  • R 21 halogen or C r C 3 alkyl
  • R 22 is C r C 3 alkyl
  • Embodiment PF A compound of Embodiment PE wherein G A is selected from G A -1, G A -2, G A -3, G A -7, G A -8 and G A -9.
  • R 2 is phenyl, 2-methylphenyl, 3-methylphenyl, 4-chlorophenyl, 3 -fluorophenyl or
  • R 3 is hydroxy
  • each R 14 , R 15 , R 18 and R 19 is H.
  • This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation a herbicidally effective amount of a compound of the invention (e.g., as a composition described herein).
  • a herbicidally effective amount of a compound of the invention e.g., as a composition described herein.
  • embodiments relating to methods of use are those involving the compounds of embodiments described above.
  • this invention also includes a herbicidal mixture comprising (a) a compound selected from Formula 1, N-oxides, and salts thereof, and (b) at least one additional active ingredient selected from (bl) photosystem II inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5) 5-enol-pyruvylshikimate-3 -phosphate (EPSP) synthase inhibitors, (b6) photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very long chain fatty acid (VLCFA) elongase inhibitors, (blO) auxin transport inhibitors, (bl 1) phytoene desaturase (PDS) inhibitors, (bl2) 4-hydroxyphenyl-pyru-pyru
  • Photosystem II inhibitors are chemical compounds that bind to the D-l protein at the Qg-binding niche and thus block electron transport from to Qg in the chloroplast thylakoid membranes.
  • the electrons blocked from passing through photosystem II are transferred through a series of reactions to form toxic compounds that disrupt cell membranes and cause chloroplast swelling, membrane leakage, and ultimately cellular destruction.
  • the Qg-binding niche has three different binding sites: binding site A binds the triazines such as atrazine, triazinones such as hexazinone, and uracils such as bromacil, binding site B binds the phenylureas such as diuron, and binding site C binds benzothiadiazoles such as bentazon, nitriles such as bromoxynil and phenyl-pyridazines such as pyridate.
  • binding site A binds the triazines such as atrazine, triazinones such as hexazinone, and uracils such as bromacil
  • binding site B binds the phenylureas such as diuron
  • binding site C binds benzothiadiazoles such as bentazon, nitriles such as bromoxynil and phenyl-pyridazines such as pyridate.
  • photosystem II inhibitors include ametryn, atrazine, cyanazine, desmetryne, dimethametryn, prometon, prometryne, propazine, simazine, simetryn, terbumeton, terbuthylazine, terbutryne, trietazine, hexazinone, metamitron, metribuzin, amicarbazone, bromacil, lenacil, terbacil, chloridazon, desmedipham, phenmedipham, chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, ethidimuron, fenuron, fluometuron, isoproturon, isouron, linuron, methabenzthiazuron, metobromuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron, propa il, pentanochlor, brom
  • AHAS inhibitors are chemical compounds that inhibit acetohydroxy acid synthase (AHAS), also known as acetolactate synthase (ALS), and thus kill plants by inhibiting the production of the branched-chain aliphatic amino acids such as valine, leucine and isoleucine, which are required for DNA synthesis and cell growth.
  • AHAS acetohydroxy acid synthase
  • ALS acetolactate synthase
  • AHAS inhibitors include amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flupyrsulfuron-methyl (including sodium salt), foramsulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron-methyl (including sodium salt), mesosulfuron-methyl, metazosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl,
  • ACCase inhibitors are chemical compounds that inhibit the acetyl-CoA carboxylase enzyme, which is responsible for catalyzing an early step in lipid and fatty acid synthesis in plants. Lipids are essential components of cell membranes, and without them, new cells cannot be produced. The inhibition of acetyl CoA carboxylase and the subsequent lack of lipid production leads to losses in cell membrane integrity, especially in regions of active growth such as meristems. Eventually shoot and rhizome growth ceases, and shoot meristems and rhizome buds begin to die back.
  • ACCase inhibitors include clodinafop, cyhalofop, diclofop, fenoxaprop, fluazifop, haloxyfop, propaquizafop, quizalofop, alloxydim, butroxydim, clethodim, cycloxydim, pinoxaden, profoxydim, sethoxydim, tepraloxydim and tralkoxydim, including resolved forms such as fenoxaprop-P, fluazifop-P, haloxyfop-P and quizalofop-P and ester forms such as clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl and fenoxaprop-P -ethyl.
  • auxin is a plant hormone that regulates growth in many plant tissues.
  • auxin mimics are chemical compounds mimicking the plant growth hormone auxin, thus causing uncontrolled and disorganized growth leading to plant death in susceptible species.
  • auxin mimics include but are not limited to aminocyclopyrachlor, aminopyralid benazolin-ethyl, chloramben, clomeprop, clopyralid, dicamba, 2,4-D, 2,4-DB, dichlorprop, fluroxypyr, mecoprop, MCPA, MCPB, 2,3,6-TBA, picloram, triclopyr, quinclorac and quinmerac.
  • EEPSP (5-enol-pyruvylshikimate-3-phosphate) synthase inhibitors are chemical compounds that inhibit the enzyme, 5 -enol-pyruvylshikimate-3 -phosphate synthase, which is involved in the synthesis of aromatic amino acids such as tyrosine, tryptophan and phenylalanine.
  • EPSP inhibitor herbicides are readily absorbed through plant foliage and translocated in the phloem to the growing points.
  • Glyphosate is a relatively nonselective postemergence herbicide that belongs to this group.
  • Glyphosate includes esters and salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium) and trimesium (alternatively named sulfosate).
  • Photosystem I electron diverters are chemical compounds that accept electrons from Photosystem I, and after several cycles, generate hydroxyl radicals. These radicals are extremely reactive and readily destroy unsaturated lipids, including membrane fatty acids and chlorophyll. This destroys cell membrane integrity, so that cells and organelles "leak", leading to rapid leaf wilting and desiccation, and eventually to plant death. Examples of this second type of photosynthesis inhibitor include paraquat and diquat.
  • PPO inhibitors are chemical compounds that inhibit the enzyme protoporphyrinogen oxidase, quickly resulting in formation of highly reactive compounds in plants that rupture cell membranes, causing cell fluids to leak out.
  • PPO inhibitors include acifluorfen-sodium, bifenox, chlomethoxyfen, fluoroglycofen-ethyl, fomesafen, halosafen, lactofen, oxyfluorfen, fluazolate, pyraflufen-ethyl, cinidon-ethyl, flumioxazin, flumiclorac-pentyl, fluthiacet-methyl, thidiazimin, oxadiazon, oxadiargyl, saflufencil, azafenidin, carfentrazone, carfentrazone-ethyl, sulfentrazone, pentoxazone, benzfendizone, butafenaci
  • GS (glutamine synthase) inhibitors are chemical compounds that inhibit the activity of the glutamine synthetase enzyme, which plants use to convert ammonia into glutamine. Consequently, ammonia accumulates and glutamine levels decrease. Plant damage probably occurs due to the combined effects of ammonia toxicity and deficiency of amino acids required for other metabolic processes.
  • the GS inhibitors include glufosinate and its esters and salts such as glufosinate-ammonium and other phosphinothricin derivatives, glufosinate-P and bilanaphos.
  • VLCFA very long chain fatty acid
  • elongase inhibitors are herbicides having a wide variety of chemical structures, which inhibit the elongase.
  • Elongase is one of the enzymes located in or near chloroplasts which are involved in biosynthesis of VLCFAs.
  • very-long-chain fatty acids are the main constituents of hydrophobic polymers that prevent desiccation at the leaf surface and provide stability to pollen grains.
  • Such herbicides include acetochlor, alachlor, butachlor, dimethachlor, dimethanamid, metazachlor, metolachlor, pethoxamid, pretilachlor, propachlor, propisochlor, pyroxasulfone, thenylchlor, diphenamid, napropamide, naproanilide, fenoxasulfone, flufenacet, indanofan, mefenacet, fentrazamide, anilofos, cafenstrole, piperophos including resolved forms such as S-metolachlor and chloroacetamides and oxyacetamides.
  • auxin transport inhibitors are chemical substances that inhibit auxin transport in plants, such as by binding with an auxin-carrier protein.
  • auxin transport inhibitors include but are not limited to naptalam (also known as N-(l-naphthyl)phthalamic acid and 2-[(l-naphthalenylamino)carbonyl]benzoic acid) and diflufenzopyr.
  • PDS phytoene desaturase inhibitors
  • bl l are chemical compounds that inhibit carotenoid biosynthesis pathway at the phytoene desaturase step.
  • PDS inhibitors include norflurzon, diflufenican, picolinafen, beflubutamide, fluridone, flurochloridone and flurtamone.
  • HPPD (4-hydroxyphenyl-pyruvate-dioxygenase) inhibitors are chemical substances that inhibit the biosynthesis of synthesis of 4-hydroxy- phenyl-pyruvate-dioxygenase.
  • HPPD inhibitors include, but are not limited to mesotrione, sulcotrione, topramezone, tefuryltrione, tembotrione, isoxachlortole, isoxaflutole, benzofenap, pyrasulfatole, pyrazolynate, pyrazoxyfen, bicyclopyrone and benzobicyclon.
  • HST homogentisate solenesyltransferase inhibitors
  • HST inhibitors include haloxydine, pyriclor and the compounds of Formulae A, B and C
  • HST inhibitors also include the compounds of Formulae D and E
  • R dl is H, CI or CF 3 ;
  • R* 12 is H, CI or Br;
  • R d3 is H or CI;
  • R d4 is H, CI or CF 3 ;
  • R d5 is CH 3 , CH 2 CH 3 or CH 2 CHF 2 ;
  • R el is H, F, CI, CH 3 or CH 2 CH 3 ;
  • R e2 is H or CF 3 ;
  • R e3 is H, CH 3 or CH 2 CH 3 ;
  • R ⁇ is H, F or Br;
  • R e5 is CI, CH 3 , CF 3 , OCF 3 or CH 2 CH 3 ;
  • R e6 is H, CH 3 , CH 2 CHF 2 or C ⁇ CH;
  • herbicides include herbicides that act through a variety of different modes of action such as mitotic disruptors (e.g., flamprop-M-methyl and fiamprop-M-isopropyl) organic arsenicals (e.g., DSMA, and MSMA), 7,8-dihydropteroate synthase inhibitors, chloroplast isoprenoid synthesis inhibitors and cell-wall biosynthesis inhibitors.
  • mitotic disruptors e.g., flamprop-M-methyl and fiamprop-M-isopropyl
  • organic arsenicals e.g., DSMA, and MSMA
  • 7,8-dihydropteroate synthase inhibitors e.g., chloroplast isoprenoid synthesis inhibitors and cell-wall biosynthesis inhibitors.
  • Other herbicides include those herbicides having unknown modes of action or do not fall into a specific category listed in (bl) through (bl2) or act through a combination of modes of action listed above.
  • herbicides examples include aclonifen, asulam, amitrole, clomezone, fluometuron, difenzoquat, bromobutide, flurenol, cinmethylin, cumyluron, dazomet, dymron, methyldymron, methiozolon, ipfencarbazone, etobenzanid, fosamine, fosamine-ammonium, metam, oxaziclomefone, oleic acid, pelargonic acid and pyributicarb.
  • herbicide safeners are substances added to a herbicide formulation to eliminate or reduce phytotoxic effects of the herbicide to certain crops. These compounds protect crops from injury by herbicides but typically do not prevent the herbicide from controlling undesired vegetation.
  • herbicide safeners include but are not limited to allidochlor, benoxacor, l-bromo-4-[(chloromethyl)sulfonyl]benzene, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, 4-(dichloroacetyl)-l-oxa-4-azospiro[4.5]decane (MON 4660),
  • Compounds of Formula la, lb or lc (where R 3 is hydroxy) can be prepared via the two-step process shown in Schemes la, lb and lc respectively.
  • Intermediate 4a, 4b or 4c can be prepared by reacting dione 2 with intermediate 3 where G 1 is a nucleophilic reaction leaving group (e.g., G 1 is a halogen, alkoxycarbonyl, haloalkylcarbonyloxy, haloalkoxycarbonyloxy, pyridinyl or imidazoyl group).
  • Reaction of intermediate 4a, 4b or 4c with the appropriate cyano compound e.g., acetone cyanohydrin, potassium cyanide, sodium cyanide
  • a base such as triethylamine or pyridine
  • a fluoride anion source such as potassium fluoride or cesium fluoride
  • a phase transfer catalyst e.g. tetrabutyl ammonium bromide, etc.
  • a solvent such as dimethylsulfoxide, N,N-dimethylformamide, acetonitrile or dichloromethane at ambient temperature to the reflux temperature of the solvent can lead to a compound of Formula la, lb or lc.
  • Formula la, lb or lc can be prepared by Process 2 (in Schemes la, lb and lc respectively) by reacting dione 2 a, 2b or 2c with intermediate 3 in the presence of a cyano compound or a fluoride anion source along with a base.

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Abstract

La présente invention concerne des composés de formule 1, comprenant tous les stéréoisomères, N-oxydes et sels de ceux-ci, A est un radical choisi dans le groupe constitué de, et B1, B2, B3, T, R1, R2 R3, R4, R5, R6, R7, R8, R9, R10, R11, R12 et R13 sont tels que définis dans la description. La présente invention concerne en outre des compositions contenant les composés de formule 1 et des procédés pour lutter contre une végétation indésirable comprenant la mise en contact de la végétation indésirable avec une quantité efficace d'un composé ou d'une composition de l'invention.
PCT/US2012/027889 2011-03-09 2012-03-06 Oxohétérocycles bis-azotés herbicides WO2012122171A1 (fr)

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Cited By (5)

* Cited by examiner, † Cited by third party
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CN103271054A (zh) * 2013-02-01 2013-09-04 张德健 一种保护性耕作玉米田复配除草剂
WO2016001119A1 (fr) 2014-07-01 2016-01-07 Bayer Cropscience Aktiengesellschaft Associations de principes actifs insecticides et fongicides
WO2019007887A1 (fr) 2017-07-06 2019-01-10 Bayer Aktiengesellschaft Associations de principes actifs insecticides et fongicides
WO2019007888A1 (fr) 2017-07-06 2019-01-10 Bayer Aktiengesellschaft Associations de principes actifs insecticides
JP2019533689A (ja) * 2016-10-28 2019-11-21 シンジェンタ パーティシペーションズ アーゲー 除草性ピリダジノン化合物

Citations (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2891855A (en) 1954-08-16 1959-06-23 Geigy Ag J R Compositions and methods for influencing the growth of plants
US3060084A (en) 1961-06-09 1962-10-23 Du Pont Improved homogeneous, readily dispersed, pesticidal concentrate
US3235361A (en) 1962-10-29 1966-02-15 Du Pont Method for the control of undesirable vegetation
US3299566A (en) 1964-06-01 1967-01-24 Olin Mathieson Water soluble film containing agricultural chemicals
US3309192A (en) 1964-12-02 1967-03-14 Du Pont Method of controlling seedling weed grasses
US3920442A (en) 1972-09-18 1975-11-18 Du Pont Water-dispersible pesticide aggregates
US4144050A (en) 1969-02-05 1979-03-13 Hoechst Aktiengesellschaft Micro granules for pesticides and process for their manufacture
US4172714A (en) 1976-12-20 1979-10-30 E. I. Du Pont De Nemours And Company Dry compactible, swellable herbicidal compositions and pellets produced therefrom
GB2095558A (en) 1981-03-30 1982-10-06 Avon Packers Ltd Formulation of agricultural chemicals
EP0080592A1 (fr) 1981-12-01 1983-06-08 AUSONIA FARMACEUTICI S.r.l. Composé vasodilatateur, procédé de préparation et compositions pharmaceutiques
DE3246493A1 (de) 1982-12-16 1984-06-20 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von wasserdispergierbaren granulaten
WO1991013546A1 (fr) 1990-03-12 1991-09-19 E.I. Du Pont De Nemours And Company Granules pesticides dispersibles ou solubles dans l'eau, obtenus a partir de liants thermo-actives
US5180587A (en) 1988-06-28 1993-01-19 E. I. Du Pont De Nemours And Company Tablet formulations of pesticides
US5208030A (en) 1989-08-30 1993-05-04 Imperial Chemical Industries Plc Active ingredient dosage device
US5232701A (en) 1990-10-11 1993-08-03 Sumitomo Chemical Company, Limited Boron carbonate and solid acid pesticidal composition
EP0568041A1 (fr) * 1992-04-28 1993-11-03 Sumitomo Chemical Company, Limited Dérivés de pyrimidone et leur usage
WO2003024222A1 (fr) 2001-09-21 2003-03-27 E. I. Du Pont De Nemours And Company Traitement arthropodicide a l'anthranilamide
JP2003327580A (ja) 2002-05-10 2003-11-19 Kureha Chem Ind Co Ltd ２−（置換ベンゾイル）チアジン誘導体、その製造方法及び除草剤
WO2006133242A2 (fr) 2005-06-07 2006-12-14 Pharmacopeia, Inc. Inhibiteurs d'azinone et de diazinone v3 utilises dans les troubles lies a la depression et au stress
WO2007088876A1 (fr) 2006-02-02 2007-08-09 Kumiai Chemical Industry Co., Ltd. Derive de pyridone et herbicide

Patent Citations (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2891855A (en) 1954-08-16 1959-06-23 Geigy Ag J R Compositions and methods for influencing the growth of plants
US3060084A (en) 1961-06-09 1962-10-23 Du Pont Improved homogeneous, readily dispersed, pesticidal concentrate
US3235361A (en) 1962-10-29 1966-02-15 Du Pont Method for the control of undesirable vegetation
US3299566A (en) 1964-06-01 1967-01-24 Olin Mathieson Water soluble film containing agricultural chemicals
US3309192A (en) 1964-12-02 1967-03-14 Du Pont Method of controlling seedling weed grasses
US4144050A (en) 1969-02-05 1979-03-13 Hoechst Aktiengesellschaft Micro granules for pesticides and process for their manufacture
US3920442A (en) 1972-09-18 1975-11-18 Du Pont Water-dispersible pesticide aggregates
US4172714A (en) 1976-12-20 1979-10-30 E. I. Du Pont De Nemours And Company Dry compactible, swellable herbicidal compositions and pellets produced therefrom
GB2095558A (en) 1981-03-30 1982-10-06 Avon Packers Ltd Formulation of agricultural chemicals
EP0080592A1 (fr) 1981-12-01 1983-06-08 AUSONIA FARMACEUTICI S.r.l. Composé vasodilatateur, procédé de préparation et compositions pharmaceutiques
DE3246493A1 (de) 1982-12-16 1984-06-20 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von wasserdispergierbaren granulaten
US5180587A (en) 1988-06-28 1993-01-19 E. I. Du Pont De Nemours And Company Tablet formulations of pesticides
US5208030A (en) 1989-08-30 1993-05-04 Imperial Chemical Industries Plc Active ingredient dosage device
WO1991013546A1 (fr) 1990-03-12 1991-09-19 E.I. Du Pont De Nemours And Company Granules pesticides dispersibles ou solubles dans l'eau, obtenus a partir de liants thermo-actives
US5232701A (en) 1990-10-11 1993-08-03 Sumitomo Chemical Company, Limited Boron carbonate and solid acid pesticidal composition
EP0568041A1 (fr) * 1992-04-28 1993-11-03 Sumitomo Chemical Company, Limited Dérivés de pyrimidone et leur usage
WO2003024222A1 (fr) 2001-09-21 2003-03-27 E. I. Du Pont De Nemours And Company Traitement arthropodicide a l'anthranilamide
JP2003327580A (ja) 2002-05-10 2003-11-19 Kureha Chem Ind Co Ltd ２−（置換ベンゾイル）チアジン誘導体、その製造方法及び除草剤
WO2006133242A2 (fr) 2005-06-07 2006-12-14 Pharmacopeia, Inc. Inhibiteurs d'azinone et de diazinone v3 utilises dans les troubles lies a la depression et au stress
WO2007088876A1 (fr) 2006-02-02 2007-08-09 Kumiai Chemical Industry Co., Ltd. Derive de pyridone et herbicide
EP1982978A1 (fr) * 2006-02-02 2008-10-22 Kumiai Chemical Industry Co., Ltd. Derive de pyridone et herbicide

Non-Patent Citations (32)

* Cited by examiner, † Cited by third party
Title
"Comprehensive Heterocyclic Chemislty", 1984, PERGAMON PRESS
"Comprehensive Heterocyclic Chemistry II", 1996, PERGAMON PRESS
"Developments in formulation technology", 2000, P.JB PUBLICATIONS
"McCutcheon's Volume 2: Functional Materials", MCCUTCHEON'S DIVISION, THE MANUFACTURING CONFECTIONER PUBLISHING CO.
"McCutclaeon's Emulsfiers and Detergents", MCCUTCHEON'S DIVISION, THE MANUFACTURING CONFECTIONER PUBLISHING CO.
"Perry's Chemical Engineer's Handbook", 1963, MCGRAW-HILL, pages: 8 - 57
"The BioPesticide Manual", 2001, BRITISH CROP PROTECTION COUNCIL
"The Pesticide Manual", 2003, BRITISH CROP PROTECTION COUNCIL
A. S. DAVIDSON; B. MILWIDSKY: "Synthetic Detergents", 1987, JOHN WILEY AND SONS
ALMISICK A. V.: "Modern Crop Protection Compounds", 2007, WILEY
BIOORG. & MED. CHEM. LETT., vol. 19, no. 16, 2009, pages 4733 - 4739
BRAND ET AL., J. AGRIC. FOOD CHEM., vol. 32, 1984, pages 221 - 226
BROWNING: "Agglomeration", CHEMICAL ENGINEERING, 4 December 1967 (1967-12-04), pages 147 - 148
CHEMISTRY - A EUROPEAN JOURNAL, vol. 15, 2009, pages 7292 - 7296
EDMUNDS, A.: "Modern Crop Protection Compounds", 2007, WILEY
EDMUNDS, A.; ALMISICK A. V.: "Modern Crop Protection Compounds", 2007, WILEY
G. W. H. CHEESEMAN; E. S. G. WERSTIUK: "Advances in Heterocyclic Chemistry", vol. 22, ACADEMIC PRESS, pages: 390 - 392
GREENE, T. W.; WUTS, P. G. M.: "Protective Groups in Organic Synthesis", 1991, WILEY
HANCE ET AL.: "Weed Control Handbook", 1989, BLACKWELL SCIENTIFIC PUBLICATIONS
J. ORG. CHEM., vol. 75, 2010, pages 945 - 947
KLINGMAN: "Weed Control as a Science", 1961, JOHN WILEY AND SONS, INC., pages: 81 - 96
M. R. GRIMMETT; B. R. T. KEENE: "Advances in Heterocyclic Chemistry", vol. 43, ACADEMIC PRESS, pages: 149 - 161
M. TISLER; B. STANOVNIK: "Advances in Heterocyclic Chemistry", vol. 9, ACADEMIC PRESS, pages: 285 - 291
M. TISLER; B. STANOVNIK: "Comprehensive Heterocyclic Chemistry", vol. 3, PERGAMON PRESS, pages: 18 - 20
MARSDEN: "Solvents Guide", 1950, LNTVRSCIENCE
ORG. LETT, vol. 0, 2008, pages 445 - 448
ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 12, 2008, pages 1201 - 1208
SISELY; WOOD: "Encyclopedia of Surface Active Agents", 1964, CHEMICAL PUBL. CO., INC.
T. L. GILCHRIST: "Comprehensive Organic Synthesis", vol. 7, PERGAMON PRESS, pages: 748 - 750
T. S. WOODS: "Pesticide Chemistry and Bioscience. The Food-Environment Challenge", 1999, THE ROYAL SOCIETY OF CHEMISTRY, article "The Formulator's Toolbox - Product Fonns for Modem Agriculture", pages: 120 - 133
TETRAHEDRON, vol. 57, 2001, pages 2689
WATKINS ET AL.: "Handbook of Insecticide Dust Diluents and Carriers", DORLAND BOOKS

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103271054A (zh) * 2013-02-01 2013-09-04 张德健 一种保护性耕作玉米田复配除草剂
WO2016001119A1 (fr) 2014-07-01 2016-01-07 Bayer Cropscience Aktiengesellschaft Associations de principes actifs insecticides et fongicides
JP2019533689A (ja) * 2016-10-28 2019-11-21 シンジェンタ パーティシペーションズ アーゲー 除草性ピリダジノン化合物
JP7004711B2 (ja) 2016-10-28 2022-01-21 シンジェンタ パーティシペーションズ アーゲー 除草性ピリダジノン化合物
WO2019007887A1 (fr) 2017-07-06 2019-01-10 Bayer Aktiengesellschaft Associations de principes actifs insecticides et fongicides
WO2019007888A1 (fr) 2017-07-06 2019-01-10 Bayer Aktiengesellschaft Associations de principes actifs insecticides

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