WO2012033548A2 - Oxo-hétérocycles et sulfono-hétérocycles bis-azotés herbicides - Google Patents

Oxo-hétérocycles et sulfono-hétérocycles bis-azotés herbicides Download PDF

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WO2012033548A2
WO2012033548A2 PCT/US2011/027737 US2011027737W WO2012033548A2 WO 2012033548 A2 WO2012033548 A2 WO 2012033548A2 US 2011027737 W US2011027737 W US 2011027737W WO 2012033548 A2 WO2012033548 A2 WO 2012033548A2
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phenyl
compound
alkyl
hydroxy
cycloalkyl
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PCT/US2011/027737
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WO2012033548A3 (fr
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Kanu Maganbhai Patel
Thomas Paul Selby
Brenton Todd Smith
Andrew Edmund Taggi
Patrick Ryan Kovacs
Atul Puri
William Louis Patzoldt
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E. I. Du Pont De Nemours And Company
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Priority claimed from PCT/US2010/047944 external-priority patent/WO2011031658A1/fr
Application filed by E. I. Du Pont De Nemours And Company filed Critical E. I. Du Pont De Nemours And Company
Priority to TW101105776A priority Critical patent/TWI549943B/zh
Priority to ARP120100774A priority patent/AR085645A1/es
Priority to UY33944A priority patent/UY33944A/es
Publication of WO2012033548A2 publication Critical patent/WO2012033548A2/fr
Publication of WO2012033548A3 publication Critical patent/WO2012033548A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond
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    • C07D405/12—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 chain containing hetero atoms as chain links
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    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
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Definitions

  • This invention relates to certain bis-nitrogen 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.
  • This invention als relates to certain bis-nitrogen oxo or sulfono heterocycles, their salts and compositions, and methods of their use for controlling undesirable vegetation.
  • 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 j is C ⁇ -Cg 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: wherein
  • X is CH
  • Y is C(O);
  • 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 phenyl, phenylsulfonyl, -W 1 (phenyl), -W ⁇ S-phenyl), -W 1 (S0 2 -phenyl),
  • cycloalkylalkyl C 6 -C 18 cycloalkylcycloalkyl, C 4 -C 14 halocycloalkylalkyl, C 5 -C 16 alkylcycloalkylalkyl, C 3 -C 12 cycloalkenyl, C 3 -C 12 halocycloalkenyl, C 2 -C ⁇ 2 alkoxyalkyl, C 3 -C ⁇ 2 alkoxyalkenyl, C 4 -C ⁇ 4 alkylcycloalkyl, C 4 -C ⁇ 4 alkoxycycloalkyl, C 4 -C ⁇ 4 cycloalkoxyalkyl, CyCi ⁇ cycloalkoxyalkoxyalkyl, C 3 -C ⁇ 4 alkoxyalkoxyalkyl, C 2 -C ⁇ 2 alkylthioalkyl, C 2 -C ⁇ 2 alkylsulfinylalkyl, C 2 -C ⁇ 2 alkylsul
  • alkylcarbonyl C 2 -C 12 haloalkylcarbonyl, C 4 -C 14 cycloalkylcarbonyl, C 2 -C 12 alkoxycarbonyl, C 4 -C ⁇ cycloalkoxycarbonyl, C5-C ⁇ 4 cycloalkylalkoxycarbonyl, C 2 -C ⁇ 2 alkylaminocarbonyl, C 3 -C ⁇ 4 dialkylaminocarbonyl, C 4 -C ⁇ 4
  • cycloalkylaminocarbonyl C 2 -C 9 cyanoalkyl, CJ-CJO hydroxyalkyl, C 4 -C 14 cycloalkenylalkyl, C 2 -C ⁇ 2 haloalkoxyalkyl, C 2 -C ⁇ 2 alkoxyhaloalkyl, C 2 -C ⁇ 2 haloalkoxyhaloalkyl, C 4 -C ⁇ 4 halocycloalkoxyalkyl, C 4 -C ⁇ 4
  • haloalkoxycarbonyl C J-CJ Q alkoxy, C J-C JO haloalkoxy, C 3 -C 12 cycloalkoxy, C 3 -C ⁇ 2 halocycloalkoxy, C 4 -C ⁇ 4 cycloalkylalkoxy, C 2 -C ⁇ o alkenyloxy, C 2 -C ⁇ o haloalkenyloxy, C 2 -C 10 alkynyloxy, C 3 -C 10 haloalkynyloxy, C 2 -C 12
  • alkoxyalkoxy C 2 -C ⁇ 2 alkylcarbonyloxy, C 2 -C ⁇ 2 haloalkylcarbonyloxy, C 4 -C ⁇ 4 cycloalkylcarbonyloxy, C 3 -C 14 alkylcarbonylalkoxy, CJ-CJ Q alkylthio, CJ-CJ Q haloalkylthio, C 3 -C 12 cycloalkylthio, CJ-CJ Q alkylsulfinyl, C J-C J Q
  • dialkylaminosulfonyl C ⁇ -C ⁇ Q alkylamino, C 2 -C ⁇ 2 dialkylamino, C ⁇ -C ⁇ Q haloalkylamino, C 2 -C ⁇ 2 halodialkylamino, C 3 -C ⁇ 2 cycloalkylamino, C 2 -C ⁇ 2 alkylcarbonylamino, C 2 -C ⁇ 2 haloalkylcarbonylamino, C ⁇ -C ⁇ Q
  • alkylsulfonylamino C ⁇ -C ⁇ Q haloalkylsulfonylamino or C 4 -C ⁇ 4
  • W 1 is C j -Cg alkylene, C 2 -C 6 alkenylene or C 2 -C 6 alkynylene;
  • W 2 is C r C 6 alkylene
  • cycloalkylalkyl C 6 -C 14 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 ⁇ o alkoxyalkenyl, C 4 -C ⁇ o cycloalkoxyalkyl, C 3 -C ⁇ o alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkylsulfonylalkyl, C 2 -C 8 alkylaminoalkyl, C 3 -C ⁇ o dialkylaminoalkyl, C 2 -C 8 haloalkylaminoal
  • alkylaminocarbonyl C 3 -C ⁇ o dialkylaminocarbonyl, C 4 -C ⁇ o
  • cycloalkylaminocarbonyl C 2 -C 5 cyanoalkyl, C j -Cg hydroxyalkyl, C 4 -C 10 cycloalkenylalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 8 haloalkoxyhaloalkyl, C 4 -C ⁇ o halocycloalkoxyalkyl, C 4 -C ⁇ o
  • haloalkoxycarbonyl C ⁇ -Cg alkoxy, C ⁇ -Cg 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 2 -Cg alkynyloxy, C 3 -Cg haloalkynyloxy, C 2 -C 8 alkoxyalkoxy, C 2 -C 8 alkylcarbonyloxy, C 2 -C 8 haloalkylcarbonyloxy, C 4 -C 10
  • alkyl(thiocarbonyl)oxy C 2 -C 8 alkylcarbonylthio, C 2 -C 8 alkyl(thiocarbonyl)thio, C 3 -C 8 cycloalkylsulfinyl, C j -Cg alkylaminosulfonyl, C 2 -C 8
  • dialkylaminosulfonyl C 3 -C ⁇ o halotrialkylsilyl, C ⁇ -Cg alkylamino, C 2 -C 8 dialkylamino, C ⁇ -Cg haloalkylamino, C 2 -C 8 halodialkylamino, C 3 -C 8 cycloalkylamino, C 2 -C 8 alkylcarbonylamino, C 2 -C 8 haloalkylcarbonylamino, C ⁇ -Cg alkylsulfonylamino, C ⁇ -Cg haloalkylsulfonylamino or C 4 -C ⁇ o
  • R 1 and R 2 are taken together along with the atoms to which they are attached to make a 5-, 6- or 7-membered unsaturated, partially unsaturated or fully unsaturated ring along with members consisting of up to 2 oxygen atoms, 2 nitrogen atoms or 2 sulfur atoms or up to two -S(O)-, -S(0) 2 -, -C(O)- groups optionally substituted on carbon atom ring members selected from halogen, cyano, C j -Cg alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C j -Cg haloalkyl, C 3 -C 8 cycloalkyl and C 2 -C 8 alkoxyalkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C j -Cg alkyl, C j -Cg alkoxy and C j -Cg
  • W 3 is C j -Cg alkylene, C 2 -C 6 alkenylene or C 2 -C 6 alkynylene;
  • W 4 is C r C 6 alkylene
  • cycloalkylalkoxy C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -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 3 -C 10
  • alkylsulfonyl -Cg haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, -Cg alkylsulfonyloxy, C j -Cg alkylamino, C 2 -C 8 dialkylamino, C j -Cg
  • haloalkylamino C 2 -C 8 halodialkylamino, C3-C 8 cycloalkylamino, C 2 -C 8 alkylcarbonylamino, C 2 -C 8 haloalkylcarbonylamino, C ⁇ -Cg alkylsulfonylamino or C ⁇ -Cg haloalkylsulfonylamino; or benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy, phenylsulfonyloxy, benzylsulfonyloxy, phenylthio, benzylthio, phenylsulfmyl, 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 j -Cg alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C j -Cg haloalkyl, C j -Cg alkoxy, C j -Cg haloalkoxy,
  • R 8 is H, C r C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C r C 6 haloalkyl, C 2 -C 6
  • R 9 is H, C r 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 -Cg haloalkynyl, C3-C 8 cycloalkyl, C3-C 8 halocycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C4-C10 halocycloalkylalkyl, C5-C ⁇ 2 alkylcycl
  • R 10 is H, halogen, cyano, hydroxy, amino, nitro, SH, -S0 2 NH 2 , -S0 2 NHCN,
  • C 3 -C 8 halocycloalkyl C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 4 -C ⁇ o halocycloalkylalkyl, C5-C ⁇ 2 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl or C 2 -C 8 alkylthioalkyl;
  • R 1 1 is H, halogen, cyano, hydroxy, amino, C j -Cg alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl,
  • R 12 is H, halogen, cyano, hydroxy, amino, C j -Cg alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C j -Cg 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 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 4 -C ⁇ o halocycloalkylalkyl, C5-C ⁇ 2 alkylcycloalkylalkyl, C3"C 8 cycloalkenyl, C3-C 8 halocycloalkenyl or C 2 -C 8 alkoxy carbonylamino;
  • 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 j -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 j -Cg haloalkyl, C 2 -C 6 haloalkenyl, C j -Cg alkoxy, C j -Cg haloalkoxy, C 3 -C 8 cycloalkoxy, C j -Cg alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 8 cycloalkyl; T is C j -Cg alkylene or C 2 -C 6 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, C4-C10 cycloalkoxyalkyl, C 3 -C ⁇ Q alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C5 cyanoalkyl, C j -Cg hydroxyalkyl, -Cg alkoxy, C j -Cg haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C4-C10 cycloalkylalkoxy, C 2 -Cg alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2
  • alkylcarbonyloxy C ⁇ -Cg alkylthio, C ⁇ -Cg haloalkylthio, C 3 -C 8 cycloalkylthio, C j -Cg alkylsulfinyl, C j -Cg haloalkylsulfinyl, -Cg alkylsulfonyl, -Cg haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, -Cg alkylamino, C 2 -C 8 dialkylamino, C ⁇ -Cg haloalkylamino, C 2 -C 8 halodialkylamino or C 3 -C 8 cycloalkylamino; and
  • each R 22 is independently -Cg alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C j -Cg
  • haloalkyl C 3 -C 8 cycloalkyl or C 2 -C 8 alkoxyalkyl.
  • 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 roup 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 method of using a compound of Formula IS as a herbicide safener.
  • This invention is also directed to a compound of Formula 1R (including all stereoisomers), N-oxides, and salts thereof:
  • R 1 is phenyl, -W 1 (phenyl), -W ⁇ S-phenyl), -W 1 (S0 2 -phenyl), -W 2 (S0 2 CH 2 -phenyl) or -W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or -W 2 G; or C ⁇ -Cg alkyl, C 2 -Cg alkenyl, C 2 -Cg alkynyl, C ⁇ -Cg haloalkyl, C 2 -Cg haloalkenyl, C3-C8 cycloalkyl, C4-C10 cycloalkylalkyl, C5-C j2 alkylcycloalkylalkyl, C3-C8 cycloalkenyl, C3-C halocycloalkenyl, C 2 -Cg alkoxyalkyl, C3-C10
  • W 1 is C j -Cg alkylene, C 2 -Cg alkenylene or C 2 -Cg alkynylene;
  • W 2 is C r C 6 alkylene
  • R 2 is phenyl or -W 3 (phenyl), each substituted on ring members with up to two
  • W 3 is C j -Cg alkylene, C 2 -C£ alkenylene or C 2 -C£ alkynylene;
  • each G is independently a 5- or 6-membered heterocyclic ring or an 8-, 9- or
  • alkylcarbonyloxy C ⁇ -Cg alkylthio, C ⁇ -Cg haloalkylthio, C 3 -C 8 cycloalkylthio, C j -Cg alkylsulfinyl, C j -Cg haloalkylsulfinyl, -Cg alkylsulfonyl, -Cg haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, -Cg alkylamino, C 2 -C 8 dialkylamino, C ⁇ -Cg haloalkylamino, C 2 -C 8 halodialkylamino or C 3 -C 8 cycloalkylamino; and
  • each R 22 is independently -Cg alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C j -Cg
  • This invention is also directed to a method of using a compound of Formula 1R as herbicide safener.
  • This invention is also directed to a compound of Formula IS (including all stereoisomers), N-oxides, and salts thereof:
  • R 1 is phenyl, -W 1 (phenyl), -W ⁇ S-phenyl), -W 1 (S0 2 -phenyl), -W 2 (S0 2 CH 2 -phenyl) or -W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or -W 2 G; or C j -Cg alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C j -Cg haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C halocycloalkenyl, C 2 -C 8 alkoxyalky
  • W 1 is C j -Cg alkylene, C 2 -C 6 alkenylene or C 2 -C 6 alkynylene;
  • W 2 is C r C 6 alkylene
  • R 2 is phenyl or -W 3 (phenyl), each substituted on ring members with up to two substituents selected from R 21 ; or -G; or C j -Cg alkyl or C 3 -C 8 cycloalkyl;
  • W 3 is C j -Cg alkylene, C 2 -C 6 alkenylene or C 2 -C 6 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 -C 8 alkoxyalkyl, C4-C 10 cycloalkoxyalkyl, C 3 -C ⁇ Q alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 5 cyanoalkyl, C j -Cg hydroxyalkyl, -Cg alkoxy, C j -Cg haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C4-C 10 cycloalkylalkoxy, C 2 -Cg alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2
  • alkylcarbonyloxy C ⁇ -Cg alkylthio, C ⁇ -Cg haloalkylthio, C 3 -C 8 cycloalkylthio, C j -Cg alkylsulfinyl, -Cg haloalkylsulfinyl, -Cg alkylsulfonyl, -Cg haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C j -Cg 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 j -Cg alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C j -Cg
  • R 23 is an optionally substituted carbon moiety
  • This invention is also directed to a method of using a compound of Formula IS as a herbicide safener.
  • This invention is also directed to a process for preparing a compound of Formula 1 from a compound of formula 1 in the presence of cesium floride:
  • A' is a radical selected from A'-l, A'-2, A'-3 and A'-5 as defined above for a compound of Formula 1Q; and A is radical selected from A-1, A-2, A-3 and A-5 as defined above for a compound of Formula 1; and R 1 and R 2 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 compounds of Formula IP (including all stereoisomers), N-oxides, and salts thereof, agricultural compositions containing them and their use as herbicides:
  • X is CH or N
  • Y is C(O) or S(0) 2 ; provided that when Y is S(0) 2 , then X is CH;
  • 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 phenyl, phenylsulfonyl, -W 1 (phenyl), -W ⁇ S-phenyl), -W 1 (S0 2 -phenyl),
  • cycloalkylalkyl C 6 -C 14 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl,
  • cycloalkylaminocarbonyl C 2 -C 5 cyanoalkyl, -Cg hydroxyalkyl, C 4 -C 10 cycloalkenylalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 8 haloalkoxyhaloalkyl, C 4 -C ⁇ o halocycloalkoxyalkyl, C 4 -C ⁇ o
  • haloalkoxycarbonyl C ⁇ -Cg alkoxy, C ⁇ -Cg 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 2 -Cg alkynyloxy, C 3 -Cg haloalkynyloxy, C 2 -C 8 alkoxyalkoxy,
  • haloalkylsulfinyl -Cg alkylsulfonyl, C j -Cg haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C 2 -C 8 alkylcarbonylthio, C 2 -C 8 alkyl(thiocarbonyl)thio,
  • dialkylaminosulfonyl C ⁇ -Cg alkylamino, C 2 -C 8 dialkylamino, C ⁇ -Cg haloalkylamino, C 2 -C 8 halodialkylamino, C 3 -C 8 cycloalkylamino, C 2 -C 8 alkylcarbonylamino, C 2 -C 8 haloalkylcarbonylammo, C ⁇ -Cg alkylsulfonylamino, C ⁇ -Cg haloalkylsulfonylamino or C 4 -C ⁇ o cycloalkyl(alkyl)amino;
  • W 1 is C j -Cg alkylene, C 2 -C 6 alkenylene or C 2 -C 6 alkynylene;
  • W 2 is C r C 6 alkylene
  • cycloalkylalkyl C 6 -C 14 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl,
  • dialkylaminocarbonyl C 4 -C ⁇ o cycloalkylaminocarbonyl, C 2 -C 5 cyanoalkyl, C j -Cg hydroxyalkyl, C 4 -C 10 cycloalkenylalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 8 haloalkoxyhaloalkyl, C 4 -C ⁇ o halocycloalkoxyalkyl,
  • haloalkylsulfinyl C j -Cg alkylsulfonyl, C j -Cg 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 ⁇ o alkoxycarbonylalkoxy, C 2 -C 8
  • alkyl(thiocarbonyl)oxy C 2 -C 8 alkylcarbonylthio, C 2 -C 8 alkyl(thiocarbonyl)thio, C 3 -C 8 cycloalkylsulfinyl, C j -Cg alkylaminosulfonyl, C 2 -C 8
  • dialkylaminosulfonyl C 3 -C ⁇ o halotrialkylsilyl, C ⁇ -Cg alkylamino, C 2 -C 8 dialkylamino, C ⁇ -Cg haloalkylamino, C 2 -C 8 halodialkylamino, C 3 -C 8 cycloalkylamino, C 2 -C 8 alkylcarbonylamino, C 2 -C 8 haloalkylcarbonylamino, C ⁇ -Cg alkylsulfonylamino, C ⁇ -Cg haloalkylsulfonylamino or C 4 -CI Q
  • W 3 is C j -Cg alkylene, C 2 -C 6 alkenylene or C 2 -C 6 alkynylene;
  • W 4 is C r C 6 alkylene
  • cycloalkylalkoxy C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -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 3 -C 10
  • alkylsulfonyl -Cg haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C j -Cg alkylsulfonyloxy, C j -Cg alkylamino, C 2 -C 8 dialkylamino, C j -Cg
  • haloalkylamino C 2 -C 8 halodialkylamino, C3-C 8 cycloalkylamino, C 2 -C 8 alkylcarbonylamino, C 2 -C 8 haloalkylcarbonylamino, C ⁇ -Cg alkylsulfonylamino or C ⁇ -Cg haloalkylsulfonylamino; or benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy, phenylsulfonyloxy, benzylsulfonyloxy, phenylthio, benzylthio, phenylsulfmyl, 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 j -Cg alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C j -Cg haloalkyl, -Cg alkoxy, C j -Cg haloalkoxy, C3"C 8 cycloalkoxy or C3-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 r 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 -Cg haloalkynyl, C3-C 8 cycloalkyl or C3-C 8 halocycloalkyl; or benzyl optionally substituted on ring members with up to five substituents selected from R 21 ;
  • R 9 is H, C r C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C r C 6 haloalkyl, C 2 -C 6
  • R 10 is H, halogen, cyano, hydroxy, amino, nitro, SH, -S0 2 NH 2
  • R 1 1 is H, halogen, cyano, hydroxy, amino, C j -Cg alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C j -Cg 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 -C 10 cycloalkylalkyl, C 4 -C 10 halocycloalkylalkyl, C5-C ⁇ 2 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 4 -C 10 cycloalkoxyalkyl, C 3 -
  • R 12 is H, halogen, cyano, hydroxy, amino, C j -Cg alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C j -Cg 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 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 4 -C ⁇ o halocycloalkylalkyl, C5-C ⁇ 2 alkylcycloalkylalkyl, C 3 -Cg cycloalkenyl, C 3 -Cg halocycloalkenyl or C 2 -Cg alkoxy carbonylamino;
  • 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 j -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 j -Cg haloalkyl, C 2 -C 6 haloalkenyl, C j -Cg alkoxy, C j -Cg haloalkoxy, C 3 -C 8 cycloalkoxy, C j -Cg alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 8 cycloalkyl; T is C j -Cg alkylene or C 2 -C 6 alkenylene;
  • each G is independently a 5- or 6-membered heterocyclic ring or an 8-, 9- or
  • alkylcarbonyloxy C ⁇ -Cg alkylthio, C ⁇ -Cg haloalkylthio, C 3 -C 8 cycloalkylthio, C j -Cg alkylsulfinyl, -Cg haloalkylsulfinyl, -Cg alkylsulfonyl, -Cg haloalkylsulfonyl, C 3 -C 8 cycloalkylsulfonyl, C j -Cg alkylamino, C 2 -C 8 dialkylamino, C ⁇ -Cg haloalkylamino, C2-C 8 halodialkylamino or C 3 -C 8 cycloalkylamino; and
  • each R 22 is independently C j -Cg alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, -Cg
  • haloalkyl C 3 -C 8 cycloalkyl or C2-C 8 alkoxyalkyl.
  • this invention pertains to a compound of Formula IP (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 includes a herbicidal mixture of (a) a compound of Formula IP and (b) an active ingredient selected from a photosystem II inhibitor.
  • compositions, 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.
  • broadleaf weed means dicot or dicotyledon, a term used to describe a group of angiosperms characterized by embryos having two cotyledons.
  • 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 .
  • alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, /-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.
  • 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 OCH 3 CH 2 OCH 2 CH 2 .
  • Alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.
  • Alkylsulfinyl 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 butylsulfmyl, pentylsulfmyl and hexylsulfmyl 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.
  • Alkylthioalkyl 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 ;
  • alkylsulfmylalkyl 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 refers to an alkylsulfmyl moiety group bonded to an oxygen atom.
  • alkyl(thiocarbonyl)oxy include CH 3 CH 2 OS(0) and CH 3 CH 2 CH 2 OS(0).
  • alkyl(thiocarbonyl)thio refers to an alkylsulfinyl moiety bonded to a sulfur atom.
  • alkyl(thiocarbonyl)thio include CH 3 CH 2 S(0)S.
  • 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, ethylcyclopropyl, 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 CF 3 0-, 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-.
  • haloalkylsulfinyl 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 HC ⁇ CCHC1-, CF 3 C ⁇ C-, 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", “cycloalkylaminocarbonyl” are defined analogously.
  • alkylcarbonylalkoxy denotes alkylcarbonyl bonded to an alkoxy moiety.
  • cycloalkylcarbonyloxy denotes a cycloalkylcarbonyl group bonded to oxygen.
  • Examples of “cycloalkylcarbonyloxy” include c-Pr-C(0)0- and c- hexyl-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 an alkoxyalkyl group. Examples of the term “cycloalkoxyalkoxyalkyl” include (tetrahydrofuran-2-yl)CH 2 OCH 2 -, (tetrahydrofuran-3-yl)CH 2 CH 2 OCH 2 - or
  • 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 trans-cycloalkylcycloalkyl isomers, (such as (li?,25)-l,l'-bicyclopropyl-2-yl and (li?,2i?)-l,l'-bicyclopropyl-2-yl).
  • cyclopropylcyclopropyl such as ⁇ , ⁇ -bicyclopropyl-l-yl, l,l'-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.
  • Examples of “cycloalkenylalkyl” 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 -.
  • C j -Cj The total number of carbon atoms in a substituent group is indicated by the "C j -Cj" prefix where i and j are numbers from 1 to 14.
  • C 1 -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 2.
  • a group contains a substituent which can be hydrogen, for example R 2 , R 3 , R 4 , R 5 , R 6 , R?, R8, R9 RI O, R n R 12 ? R 13 ? R 14 R 15 ? R 18 ? R 19 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 1 then hydrogen may be at the position 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.
  • 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. Typically a heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs. Unless otherwise indicated, a heterocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring. When a fully unsaturated heterocyclic ring satisfies Huckel's rule, then said ring is also called a “heteroaromatic ring” or “aromatic heterocyclic ring”. Unless otherwise indicated, 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 Huckel's rule.
  • aromatic ring system denotes a carbocyclic or heterocyclic ring system in which at least one ring of the ring system is aromatic.
  • aromatic carbocyclic ring system denotes a carbocyclic ring system in which at least one ring of the ring system is aromatic.
  • aromatic heterocyclic ring system denotes a heterocyclic ring system in which at least one ring of the ring system is aromatic.
  • nonaromatic ring system denotes a carbocyclic or heterocyclic ring system that may be fully saturated, as well as partially or fully unsaturated, provided that none of the rings in the ring system are aromatic.
  • nonaromatic carbocyclic ring system denotes a carbocylcic ring system in which no ring in the ring system is aromatic.
  • nonaromatic heterocyclic ring system denotes a heterocyclic ring system in which no ring in the ring system is aromatic.
  • an optionally substituted group may have a substituent at each substitutable position of the group, and each substitution is independent of the other.
  • G When G is a 5- or 6-membered nitrogen-containing 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 unsaturated aromatic heterocyclic ring optionally substituted with from one or more substituents include the rings Q-l through Q-60 illustrated in Exhibit 1 wherein R v 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 saturated or unsaturated non-aromatic 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 saturated or non-aromatic unsaturated heterocyclic ring include the rings U-l through U-36 as illustrated in Exhibit 2. 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 ).
  • 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 3 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-1 through Q-5, Q-7 through Q-48, and Q-52 through Q-60).
  • R 1 and R 2 are taken together along with the atoms to which they are attached to make a 5-, 6- or 7-membered unsaturated, partially unsaturated or fully unsaturated ring along with members consisting of up to 2 oxygen atoms, 2 nitrogen atoms or 2 sulfur atoms or up to two -S(O)-, -S(0) 2 -, -C(O)- groups.
  • R 1 and R 2 may also be connected to form a ring fused to the ring to which they are attached.
  • the fused ring can be a 5-, 6- or 7-membered ring including as ring members the two atoms shared with the ring to which the substituents are attached.
  • the other 3, 4 or 5 ring members of the fused ring are provided by R 1 and R 2 substituents taken together.
  • These other ring members can include up to 5 carbon atoms (as allowed by the ring size) and optionally up to 3 heteroatoms selected from up to 2 O, up to 2 S and up to 3 N.
  • the fused ring is optionally substituted with up to 3 substituents as noted in the Summary of the Invention.
  • Exhibit 4 provides, as illustrative examples, rings formed by R 1 and R 2 taken together.
  • the optional substituents (R v ) r are independently selected from the group consisting of halogen, cyano, i ⁇ C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci ⁇ C 6 haloalkyl, C 3 -C 8 cycloalkyl and C 2 -C 8 alkoxyalkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, Ci ⁇ C 6 alkyl, Ci ⁇ C 6 alkoxy and i ⁇ C 6 haloalkoxy; on carbon atom ring members.
  • the optional substituents (R v ) r are independently selected from the group consisting of H and i ⁇ C 6 alkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, Ci ⁇ C 6 alkyl, i-C ⁇ alkoxy and Ci-C ⁇ haloalkoxy; on nitrogen ring members. Substituents are limited by the number of available positions on each T-ring. When the attachment point between (R v ) r and the T-ring is illustrated as floating, R v may be bonded to any available T-ring carbon or nitrogen atom (as applicable).
  • r is nominally an integer from 0 to 3
  • some of the rings shown in Exhibit 4 have less than 3 available positions, and for these groups r is limited to the number of available positions.
  • r is 0 this means the ring is unsubstituted and hydrogen atoms are present at all available positions. If r is 0 and (R v ) r is shown attached to a particular atom, then hydrogen is attached to that atom.
  • the nitrogen atoms that require substitution to fill their valence are substituted with H or R v .
  • some of the rings shown in Exhibit 4 can form tautomers, and the particular tautomer depicted is representative of all the possible tautomers.
  • 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.
  • Noncrystalline 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 m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane.
  • MCPBA peroxy acids
  • alkyl hydroperoxides such as t-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 wherein 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- 1 , 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-l .
  • 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 5 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-l .
  • 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 1 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 1 1 wherein B 3 is C-l .
  • Embodiment 13 A compound of Formula 1 or any one of Embodiments 1 through 1 1 wherein B 3 is C-2.
  • alkylcarbonyl C 2 -C 12 haloalkylcarbonyl, C 4 -C 14 cycloalkylcarbonyl, C 2 -C 12 alkoxycarbonyl, C 4 -C ⁇ 6 cycloalkoxycarbonyl, C5-C ⁇ 4 cycloalkylalkoxycarbonyl, C 2 -C ⁇ 2 alkylaminocarbonyl, C 3 -C ⁇ 4 dialkylaminocarbonyl, C 4 -C ⁇ 4
  • cycloalkylaminocarbonyl C 2 -C 9 cyanoalkyl, CJ-CJ Q hydroxyalkyl, C 4 -C 14 cycloalkenylalkyl, C 2 -C ⁇ 2 haloalkoxyalkyl, C 2 -C ⁇ 2 alkoxyhaloalkyl, C 2 -C ⁇ 2 haloalkoxyhaloalkyl, C 4 -C ⁇ 4 halocycloalkoxyalkyl, C 4 -C ⁇ 4
  • Embodiment 15 A compound of Formula 1 or any one of Embodiments 1 through 14 wherein R 1 is phenyl, phenylsulfonyl, -W 1 (phenyl), -W ⁇ S-phenyl),
  • cycloalkylalkyl C 6 -C 14 cycloalkylcycloalkyl, C 4 -C 10 halocycloalkylalkyl,
  • dialkylaminocarbonyl C 4 -C ⁇ o cycloalkylaminocarbonyl, C 2 -C5 cyanoalkyl, Ci-Cfr hydroxyalkyl, C 4 -C 10 cycloalkenylalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 8 haloalkoxyhaloalkyl, C 4 -C ⁇ o halocycloalkoxyalkyl, C 4 -C 10 cycloalkenyloxyalkyl, C 4 -C 10 halocycloalkenyloxyalkyl, C 3 -C 10 dialkoxyalkyl, C 3 -C ⁇ o alkoxyalkylcarbonyl, C 3 -C ⁇ o alkoxycarbonylalkyl or C 2 -C 8 haloalkoxycarbonyl.
  • Embodiment 16 A compound of Embodiment 15 wherein R 1 is phenyl, -W ⁇ phenyl), -W ⁇ S-phenyl), -W 1 (S0 2 -phenyl), -W 2 (S0 2 CH 2 -phenyl) or -W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R21 ; or -G or -W 2 G; or C R C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C R C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2
  • alkoxycycloalkyl C 3 -C ⁇ o alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl or C 2 -C 8 alkylsulfonylalkyl .
  • Embodiment 17 A compound of Embodiment 16 wherein R 1 is phenyl or
  • -W 1 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or -G or -W 2 G; or Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci ⁇ C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -Cg alkoxyalkyl C 3 -C I Q alkoxyalkenyl, C4-C 10
  • alkylcycloalkyl or C4-C 10 alkoxycycloalkyl are examples of alkylcycloalkyl or C4-C 10 alkoxycycloalkyl.
  • Embodiment 18 A compound of Embodiment 17 wherein R 1 is phenyl,
  • Embodiment 19 A compound of Embodiment 18 wherein R 1 is phenyl, 4-ethylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl,
  • Embodiment 20 A compound of Embodiment 19 wherein R 1 is phenyl,
  • Embodiment 21 A compound of Embodiment 20 wherein R 1 is phenyl.
  • Embodiment 22 A compound of Embodiment 19 wherein R 1 is 3,4-dimethoxyphenyl.
  • Embodiment 23 A compound of Embodiment 19 wherein R 1 is 5-chloro-2- methylphenyl.
  • Embodiment 24 A compound of Formula 1 or any one of Embodiments 1 through 21 wherein R 1 is other than phenyl.
  • Embodiment 25 A compound of Embodiment 17 wherein R 1 is -G or -W 2 G; Ci-C ⁇ alkyl, C 3 -C 8 cycloalkyl, or C 2 -C 8 alkoxyalkyl.
  • Embodiment 26 A compound of Embodiment 25 wherein R 1 is -G or -W 2 G.
  • Embodiment 27 A compound of Embodiment 26 wherein R 1 is Ci-C ⁇ alkyl, C 3 -Cg cycloalkyl, or C 2 -Cg alkoxyalkyl.
  • Embodiment 28 A compound of Embodiment 27 wherein R 1 is n-Vr, z ' -Pr, n- u,
  • Embodiment 29 A compound of Embodiment 28 wherein R 1 is n-Vr, c-hexyl,
  • Embodiment 29a A compound of Embodiment 29 wherein R 1 is n-Vr or
  • Embodiment 29b A compound of Embodiment 29 wherein R 1 is c-hexyl.
  • Embodiment 30 A compound of Formula 1 or any one of Embodiments 1 through 17 wherein W 1 is i ⁇ C 6 alkylene.
  • Embodiment 31 A compound of Embodiment 30 wherein W 1 is -CH 2 -.
  • Embodiment 32 A compound of Formula 1 or any one of Embodiments 1 through 17,
  • Embodiment 33 A compound of Formula 1 or any one of Embodiments 1 through 32 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; Ci-C 6 alkyl, C 2 - C 6 alkenyl, C 2 -C 6 alkynyl, Ci ⁇ 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, C4-C10 cycloalkylalkyl, C ⁇ -C ⁇ cycloalkylcycloalkyl, C4-C10
  • halocycloalkylalkyl C5-C ⁇ 2 alkylcycloalkylalkyl, C3-C 8 cycloalkenyl, C3-C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 3 -C 10 alkoxyalkenyl, C 4 -C 10
  • cycloalkoxyalkyl C4-C10 cycloalkoxylalkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkylsulfonylalkyl, C 2 -C 8 alkylcarbonyl, C4-C10 cycloalkenylalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 8 haloalkoxyhaloalkyl, C4-C10 halocycloalkoxyalkyl, C 4 -C 10 cycloalkenyloxyalkyl, C 4 -C 10 halocycloalkenyloxyalkyl, C 3 -C 10 dialkoxyalkyl, i-C ⁇ alkoxy, i-
  • cycloalkylcarbonyloxy C 3 -C 10 alkylcarbonylalkoxy, i ⁇ C 6 alkylthio, i ⁇ C 6 haloalkylthio, C 3 -C 8 cycloalkylthio, i ⁇ C 6 alkylsulfinyl, Ci ⁇ C 6
  • haloalkylsulfinyl Ci ⁇ C 6 alkylsulfonyl, Ci ⁇ 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, C3-C10 alkoxycarbonylalkoxy, C 2 -C 8
  • Embodiment 34 A compound of Embodiment 33 wherein R 2 is phenyl or
  • Embodiment 35 A compound of Embodiment 34 wherein R 2 is phenyl optionally substituted on ring members with up to two substituents selected from R 21 ; or -G; or Ci-Cfr alkyl, C 3 -C 8 cycloalkyl.
  • Embodiment 36 A compound of Embodiment 35 wherein R 2 is phenyl,
  • Embodiment 36a A compound of Embodiment 35 wherein R 2 is phenyl, 3- bromophenyl, 3-chlorophenyl, or 2-methylphenyl.
  • Embodiment 37 A compound of Embodiment 35 wherein R 2 is phenyl.
  • Embodiment 38 A compound of Formula 1 or any one of Embodiments 1 through 36 wherein R 2 is other than phenyl.
  • Embodiment 39 A compound of Embodiment 35 wherein R 2 is 3-thienyl or 2-thienyl.
  • Embodiment 40 A compound of Embodiment 35 wherein R 2 is /? -propyl, /? -butyl, or cyclopropyl.
  • Embodiment 41 A compound of Formula 1 or any one of Embodiments 1 through 13 wherein R 1 and R 2 are taken together along with the atoms to which they are attached to make a 6- or 7-membered unsaturated, partially unsaturated or fully unsaturated ring along with members consisting of up to 2 oxygen atoms, 2 nitrogen atoms or 2 sulfur atoms or up to two -S(O)-, -S(0) 2 -, -C(O)- groups optionally substituted on carbon atom ring members selected from halogen, cyano, i ⁇ C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci ⁇ C 6 haloalkyl, C 3 -C 8 cycloalkyl and C 2 -C 8 alkoxyalkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, Ci ⁇ C 6 alkyl, Ci ⁇ C 6 alk
  • Embodiment 42 A compound of Embodiment 41 wherein R 1 and R 2 are taken
  • Embodiment 43 A compound of Embodiment 42 wherein R 1 and R 2 are taken
  • Embodiment 44 A compound of Embodiment 43 wherein R 1 and R 2 are taken
  • Embodiment 45 A compound of Formula 1 or any one of Embodiments 1 through 34 wherein W 3 is -CH 2 -.
  • Embodiment 46 A compound of Formula 1 or any one of Embodiments 1 through 32 wherein W 4 is -CH 2 -.
  • Embodiment 47 A compound of Formula 1 or any one of Embodiments 1 through 46 wherein R 3 is hydroxy, -O M + , C 2 -C 8 alkylcarbonyloxy, C 2 -C 8
  • haloalkylcarbonyloxy C4-C10 cycloalkylcarbonyloxy or C 3 -CIQ alkylcarbonylalkoxy; or benzyloxy, phenyloxy, benzylcarbonyloxy,
  • Embodiment 48 A compound of Embodiment 47 wherein R 3 is hydroxy, -O M + or C 2 -C 8 alkylcarbonyloxy; or phenylsulfonyloxy optionally substituted with up to two substituents selected from R 21 .
  • Embodiment 49 A compound of Embodiment 48 wherein M + is a sodium or
  • Embodiment 50 A compound of Embodiment 49 wherein R 3 is hydroxy or C2 ⁇ Cg alkylcarbonyloxy.
  • Embodiment 51 A compound of Embodiment 50 wherein R 3 is hydroxy or
  • Embodiment 52 A compound of Formula 1 or any one of Embodiments 1 , 7 and 14 through 51 wherein R 4 , R 5 , R 6 and R 7 are each independently H, or i-C ⁇ alkyl.
  • Embodiment 53 A compound of Formula 1 or any one of Embodiments 1 , 7 and 14 through 52 wherein R 8 is i ⁇ C 6 alkyl or C 3 -C 8 cycloalkyl.
  • Embodiment 54 A compound of Embodiment 53 wherein R 8 is CH 3 , CH2CH3 or cyclopropyl.
  • Embodiment 55 A compound of Formula 1 or any one of Embodiments 1 through 3, 7 and 14 through 51 wherein R 9 is C j -C 6 alkyl.
  • Embodiment 56 A compound of Embodiment 55 wherein R 9 is CH2CH3.
  • Embodiment 57 A compound of Formula 1 or any one of Embodiments 1 through 3, 7 and 14 through 51 wherein R 10 is H, halogen or i-C ⁇ alkyl.
  • Embodiment 58 A compound of Embodiment 57 wherein R 10 is H or CH 3 .
  • Embodiment 59 A compound of Formula 1 or any one of Embodiments 1 , 2, 8, 10 and
  • R 1 1 is H or i-C ⁇ alkyl.
  • Embodiment 60 A compound of Embodiment 59 wherein R 1 1 is H.
  • Embodiment 61 A compound of Formula 1 or any one of Embodiments 1 , 2, 8, 10 and 12 through 51 wherein R 12 is H, halogen, cyano, hydroxy, amino or Ci ⁇ C 6 alkyl.
  • Embodiment 62 A compound of Embodiment 61 wherein R 12 is H, halogen, cyano,
  • Ci-Cfr alkyl or C 3 -C 8 cycloalkyl are Ci-Cfr alkyl or C 3 -C 8 cycloalkyl.
  • Embodiment 63 A compound of Embodiment 62 wherein R 12 is CH 3 , CH 2 CH 3 or cyclopropyl.
  • Embodiment 64 A compound of Formula 1 or any one of Embodiments 7 and 15
  • R 13 is H, halogen, cyano or nitro.
  • Embodiment 65 A compound of Embodiment 64 wherein R 13 is cyano or nitro.
  • Embodiment 66 A compound of Formula 1 or any one of Embodiments 1 through 65 wherein when instances of 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 r C 6 alkyl.
  • Embodiment 67 A compound of Embodiment 66 wherein when instances of R 1 and
  • R 18 are taken alone, then independently said instances of R 14 and R 18 are H or CH 3 .
  • Embodiment 68 A compound of Embodiment 68 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 70 A compound of Formula 1 or any one of Embodiments 1 through 68 wherein all instances of R 14 and R 18 are taken alone.
  • Embodiment 71 A compound of Formula 1 or any one of Embodiments 1 through 70 wherein independently each R 15 and R 19 is H or i-C ⁇ alkyl.
  • Embodiment 72 A compound of Embodiment 71 wherein independently each R 15 and
  • R 19 is H or CH 3 .
  • Embodiment 73 A compound of Embodiment 72 wherein independently each R 15 and R 19 is H.
  • Embodiment 73a A compound of Embodiments 67 and 72 wherein each R 14 , R 15 , R 18 and R 19 is H or CH 3 .
  • Embodiment 73b A compound of Embodiment 73 wherein each R 14 , R 15 , R 18 and R 19 is H.
  • Embodiment 74 A compound of Formula 1 or any one of Embodiments 1 through 73 wherein R 20 is H, Ci ⁇ C 6 alkyl, C 2 -C 6 alkenyl or C 3 -C 8 cycloalkyl.
  • Embodiment 75 A compound of Embodiment 74 wherein R 20 is H or CH 3 .
  • Embodiment 76 A compound of Formula 1 or any one of Embodiments 1 through 4,
  • Embodiment 77 A compound of Embodiment 76 wherein T is -CH 2 CH 2 -.
  • Embodiment 78 A compound of Formula 1 or any one of Embodiments 1 through 17 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 79 A compound of Embodiment 78 wherein G is
  • G-16 G-17 G-18 G-19 G-20 r is 0, 1, 2 or 3.
  • Embodiment 80 A compound of Embodiment 79 wherein G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20.
  • Embodiment 81 A compound of Embodiment 79 wherein when R 1 is G, then G is G-18, G-19 or G-20.
  • Embodiment 82 A compound of Embodiment 81 wherein when R 1 is G, then G is G-19 or G-20.
  • Embodiment 83 A compound of Embodiment 82 wherein when R 1 is G, then G is G-20.
  • Embodiment 84 A compound of Embodiment 82 wherein when R 1 is G, then G is G-19.
  • Embodiment 85 A compound of Embodiment 79 wherein when R 2 is G, then G is G-2, G-3 or G-15.
  • Embodiment 86 A compound of Embodiment 84 wherein when R 2 is G, then G is G-2 or G-3.
  • Embodiment 87 A compound of Embodiment 84 wherein when R 2 is G, then G is G-2.
  • Embodiment 88 A compound of Embodiment 84 wherein when R 2 is G, then G is G-3.
  • Embodiment 89 A compound of Formula 1 or any one of Embodiments 1 through 88 wherein each R 21 is independently halogen, cyano, hydroxy, nitro, -CHO, -SH, Ci-Cfr alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci ⁇ 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 -C 10 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 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkoxyhaloalkyl, C 2 -C 5 cyanoalkyl, Ci ⁇ C 6 hydroxyalkyl, Ci ⁇ C 6 alkoxy, i ⁇ C 6 haloalkoxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 halocycloalkoxy, C 4 -CIQ
  • alkoxyalkoxy C 2 -C 8 alkylcarbonyloxy, Ci-C ⁇ alkylthio, Ci-C ⁇ haloalkylthio,
  • Embodiment 90 A compound of Embodiment 91 wherein each R 21 is independently halogen, nitro, i ⁇ C 6 alkyl, Ci ⁇ C 6 haloalkyl, Ci ⁇ C 6 alkoxy, i ⁇ C 6 haloalkoxy or C r C 6 alkylthio.
  • Embodiment 91 A compound of Embodiment 92 wherein each R 21 is independently fluorine, chlorine, bromine, CH 3 , CF 3 , OCH 3 , OCF 3 or SCH 3 .
  • Embodiment 92 A compound of Formula 1 or any one of Embodiments 1 through 91 wherein each R 22 is independently i-C ⁇ alkyl or i-C ⁇ haloalkyl.
  • Embodiment 93 A compound of Embodiment 92 wherein each R 22 is independently
  • Embodiment 94A A compound of Formula 1 or any one of Embodiments 1 through 14 wherein R 1 is phenyl optionally substituted with up to five substituents selected from R 21 ; or -G or -W 2 G; C 4 -C 10 alkylcycloalkyl, C 4 -C 10
  • cycloalkylalkyl C 2 -C 8 alkoxyalkyl, C 4 -C 10 alkoxy cycloalkyl, C 2 -C 8
  • alkylthioalkyl C 2 -C 8 alkylsulfinylalkyl, C 2 -C 8 alkylsulfonylalkyl, C 2 -C 8 haloalkoxyalkyl, C 3 -C ⁇ o dialkoxyalkyl or C 3 -C ⁇ o alkoxycarbonylalkyl or C 2 -C 8 haloalkoxycarbonyl.
  • Embodiment 95 A A compound of Embodiment 94A wherein R 1 is phenyl,
  • Embodiment 96A A compound of Embodiment 95 A wherein R 1 is 4-methoxyphenyl.
  • Embodiment 97A A compound of Embodiment 95 A wherein R 1 is
  • Embodiment 98A A compound of Embodiment 95 a wherein R 1 is other than phenyl.
  • Embodiment 99A A compound of Embodiment 95 A wherein R 1 is
  • Embodiment 100A A compound of Embodiment 94A wherein R 1 is -G or -W 2 G.
  • Embodiment 101 A A compound of Embodiment 100A wherein R 1 is -W 2 G.
  • Embodiment 102 A A compound of Embodiment 100 A or 101 A wherein G is G-9 or G-15.
  • Embodiment 103 A A compound of Embodiment 102A wherein W 2 is -CH 2 - and G is tetrahydrofuran-2-yl.
  • Embodiment 104A A compound of Embodiment 103 A wherein R 1 is
  • Embodiment 105 A A compound of Embodiment 94A wherein R 1 is
  • Embodiment 106A A compound of Embodiment 105 A wherein R 1 is
  • Embodiment 107A A compound of Embodiment 106A wherein R 1 is
  • Embodiment 108 A A compound of Embodiment 106A wherein R 1 is
  • Embodiment 109A A compound of Embodiment 106A wherein R 1 is
  • Embodiment 110A A compound of Embodiment 106A wherein R 1 is of
  • Embodiment 111A A compound of Embodiment 105A wherein R 1 is -CH 2 CH 2 SCH 3 ,
  • Embodiment 112A A compound of Embodiment 111A wherein R 1 is -CH 2 CH 2 SCH 3 , -CH 2 CH 2 SCH 2 CH 3 , -CH 2 CH 2 SOCH 3 , -CH 2 CH 2 SOCH 2 CH 3 ,
  • Embodiment 113 A A compound of Embodiment 112A wherein R 1 is
  • Embodiment 1 14A A compound of Embodiment 29 wherein R 1 is n-Pr.
  • Embodiment 1 15 A A compound of Embodiment 29 wherein R 1 is -CH2CH2OCH3.
  • Embodiment 1 16A A compound of Embodiment 34 wherein R 2 is phenyl or
  • Embodiment 1 17A A compound of Embodiment 1 16A wherein R 2 is -G.
  • Embodiment 1 18 A A compound of Embodiment 1 17A wherein R 2 is 3-thienyl
  • Embodiment 1 19A A compound of Embodiment 1 18A wherein R 2 is 3-pyridinyl.
  • Ci-Cft alkyl C2 ⁇ Cg alkoxyalkyl, C4-C10 alkoxycycloalkyl or C3-C10 alkoxy alkoxy alky 1.
  • This invention also includes a herbicidal mixture comprising (a) a compound of Formula 1 and (b) at least one additional active ingredient selected from (bl) photosystem II inhibitors, (b2) AHAS inhibitors, (b3) ACCase inhibitors, (b4) auxin mimics and (b5) EPSP inhibitors.
  • This invention also includes a herbicidal mixture comprising (a) a compound of Formula 1 and (b) at least one additional active ingredient selected from (b6) photosystem I electron diverters, (b7) PPO (protoporphyrinogen oxidase) inhibitors, (b8) GS (glutamine synthetase) inhibitors, (b9) VLCFA (very long chain fatty acid) elongase inhibitors, (blO) auxin transport inhibitors, (bl 1) PDS (phytoene desaturase) inhibitors, (bl2) HPPD (4-hydroxyphenyl-pyruvate-dioxygnase) inhibitors, (bl3) HST (homogentisate solenesyltransfererase) inhibitors, (bl4) other herbicides including mitotic disrupters, organic arsenicals, asulam, difenzoquat, bromobutide, flurenol, cinmethylin, cumyluron, dazomet, dy
  • Embodiment 94 A herbicidal mixture comprising (a) a compound of Formula 1 and
  • Embodiment 95 A herbicidal mixture comprising (a) a compound of Formula 1 and
  • Embodiment 96 A herbicidal mixture of Embodiment 95 comprising (a) a compound of Formula 1 and (b) one additional active ingredient selected from the group consisting of ametryn, amicarbazone, atrazine, bentazon, bromacil, bromoxynil, chlorotoluron, dimethametryn, diuron, hexazinone, isoproturon, metribuzin, pyridate, simazine and terbutryn.
  • one additional active ingredient selected from the group consisting of ametryn, amicarbazone, atrazine, bentazon, bromacil, bromoxynil, chlorotoluron, dimethametryn, diuron, hexazinone, isoproturon, metribuzin, pyridate, simazine and terbutryn.
  • Embodiment 97 A herbicidal mixture of Embodiment 95 comprising (a) a compound of Formula 1; and (b) bromoxynil.
  • Embodiment 98 A herbicidal mixture of Embodiment 95 comprising (a) a compound of Formula 1; and (b) dimethametryn.
  • Embodiment 99 A herbicidal mixture comprising (a) a compound of Formula 1 and
  • Embodiment 100B A herbicidal mixture comprising (a) a compound of Formula 1 and
  • (b) at least one additional active ingredient selected from (bl), (b2), (b3), (bl3) and (b 15).
  • Embodiment 10 IB A herbicidal mixture comprising (a) a compound of Formula 1 and (b) at least one additional active ingredient selected from (bl 3) HST
  • Embodiment 102B A herbicidal mixture comprising (a) a compound of Formula 1 and (b) at least one additional active ingredient selected from (bl 3) HST
  • Embodiment 103B A herbicidal mixture of Embodiment 102B comprising (a) a
  • Embodiment 104B A herbicidal mixture of Embodiment 10 IB comprising (a) a
  • compound of Formula 1 and (b) at least one additional active ingredient selected from (bl5) herbicide safeners.
  • Embodiment 105B A herbicidal mixture of Embodiment 104B comprising (a) a
  • Embodiment 106B A herbicidal mixture of Embodiment 105B comprising (a) a
  • Embodiment 107B A herbicidal mixture of Embodiment 106B comprising (a) a
  • compound of Formula 1 and (b) at least one additional active ingredient selected from cloquintocet-mexyl, mefenpyr-diethyl and oxabetrinil.
  • Embodiment 108B A herbicidal mixture or Embodiment 107B comprising (a) a
  • Embodiment 109B A herbicidal mixture of Embodiment 108B wherein the one additional active ingredient is mefenpyr-diethyl.
  • Embodiment HOB A herbicidal mixture of Embodiment 108B wherein the at least one additional active ingredient is cloquintocet-mexyl.
  • Embodiment 11 IB A herbicidal mixture of Embodiment 94 or 100B comprising (a) a compound of Formula 1 and (b) at least one additional active ingredient selected from (b2) AH AS inhibitors.
  • Embodiment 112B A herbicidal mixture of Embodiment 11 IB wherein the at least one additional active ingredient is selected from 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,
  • Embodiment 113B A herbicidal mixture of Embodiment 112B wherein the at least one additional active ingredient is selected from azimsulfuron, bensulfuron- methyl, chlorimuron-ethyl, chlorsulfuron, metsulfuron-methyl, nicosulfuron, rimsulfuron and thifensulfuron-methyl.
  • Embodiment 114B A herbicidal mixture of Embodiment 113B wherein the at least one additional active ingredient is selected from azimsulfuron and bensulfuron- methyl.
  • Embodiment A A compound of Formula 1 wherein
  • A is A-l, A-3, A-4, A-5 or A-6;
  • R 1 is phenyl, phenylsulfonyl, -W 1 (phenyl), -W ⁇ S-phenyl), -W 1 (S0 2 -phenyl),
  • cycloalkylalkyl C 6 -C 18 cycloalkylcycloalkyl, C 4 -C 14 halocycloalkylalkyl, C 5 -C 16 alkylcycloalkylalkyl, C 3 -C 12 cycloalkenyl, C 3 -C 12 halocycloalkenyl, C 2 -C ⁇ 2 alkoxyalkyl, C 3 -C ⁇ 2 alkoxyalkenyl, C 4 -C ⁇ 4 alkylcycloalkyl, C 4 -C ⁇ 4 alkoxycycloalkyl, C 4 -C ⁇ 4 cycloalkoxyalkyl, CyCi ⁇ cycloalkoxyalkoxyalkyl, C 3 -C ⁇ 4 alkoxyalkoxyalkyl, C 2 -C ⁇ 2 alkylthioalkyl, C 2 -C ⁇ 2 alkylsulfinylalkyl, C 2 -C ⁇ 2 alkylsulf
  • alkylcarbonyl C 2 -C 12 haloalkylcarbonyl, C 4 -C 14 cycloalkylcarbonyl, C 2 -C 12 alkoxycarbonyl, C 4 -C ⁇ 6 cycloalkoxycarbonyl, C5-C ⁇ 4 cycloalkylalkoxycarbonyl, C 2 -C ⁇ 2 alkylaminocarbonyl, C 3 -C ⁇ 4 dialkylaminocarbonyl, C 4 -C ⁇ 4
  • cycloalkylaminocarbonyl C 2 -C 9 cyanoalkyl, C 1 -C 1 0 hydroxyalkyl, C 4 -C 14 cycloalkenylalkyl, C 2 -C ⁇ 2 haloalkoxyalkyl, C 2 -C ⁇ 2 alkoxyhaloalkyl, C 2 -C ⁇ 2 haloalkoxyhaloalkyl, C 4 -C ⁇ 4 halocycloalkoxyalkyl, C 4 -C ⁇ 4
  • cycloalkenyloxyalkyl C 4 -C ⁇ 4 halocycloalkenyloxyalkyl, C 3 -C ⁇ 4 dialkoxyalkyl, C 3 -C ⁇ 4 alkoxyalkylcarbonyl, C 3 -C ⁇ 4 alkoxycarbonylalkyl or C 2 -C ⁇ 2
  • cycloalkylalkyl C 6 -C 14 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 ⁇ o alkoxyalkenyl, C 4 -C ⁇ o cycloalkoxyalkyl, C 4 -C ⁇ o cycloalkoxylalkoxyalkyl, C 3 -C ⁇ o alkoxyalkoxyalkyl, C 2 -Cg alkylthioalkyl, C 2 - C 8 alkylsulfinylalkyl, C 2 -C 8 alkylsulfonylalkyl, C 2 -C 8 alkylcarbonyl, C 4 -C 10 cycloalkeny
  • cycloalkenyloxyalkyl C 4 -C ⁇ o halocycloalkenyloxyalkyl, C 3 -C ⁇ o dialkoxyalkyl, Ci-Cft alkoxy, i-C ⁇ haloalkoxy, C 3 -Cg cycloalkoxy, C 3 -Cg halocycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 haloalkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C6 haloalkynyloxy, C 2 -Cg alkoxyalkoxy, C 2 -Cg
  • W 3 is -CH 2 -;
  • W 4 is -CH 2 -;
  • R 1 and R 2 are taken together along with the atoms to which they are attached to make a 6- or 7-membered unsaturated, partially unsaturated or fully unsaturated ring along with members consisting of up to 2 oxygen atoms, 2 nitrogen atoms or 2 sulfur atoms or up to two -S(O)-, -S(0) 2 -, -C(O)- groups optionally substituted on carbon atom ring members selected from halogen, cyano, i ⁇ C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci ⁇ C 6 haloalkyl, C 3 -C 8 cycloalkyl and C 2 -C 8 alkoxyalkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, i-C ⁇ alkyl, i-C ⁇ alkoxy and Ci-C ⁇ haloalkoxy; and optionally substituted on nitrogen
  • R 3 is hydroxy, -O M + , C 2 -C 8 alkylcarbonyloxy, C 2 -C 8 haloalkylcarbonyloxy, C 4 -C 10 cycloalkylcarbonyloxy or C 3 -C ⁇ o 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 r C 6 alkyl
  • R 10 is H, halogen or Ci ⁇ C 6 alkyl
  • R 1 1 is H or C r C 6 alkyl
  • R 12 is H, halogen, cyano, hydroxy, amino or Ci ⁇ C 6 alkyl
  • R 13 is cyano or nitro
  • 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 79);
  • r is 0, 1 , 2 or 3;
  • each R 21 is independently halogen, cyano, hydroxy, nitro, -CHO, -SH, Ci ⁇ C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci ⁇ 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 -C 10 cycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C4-C10 cycloalkoxyalkyl, C 3 -Cio alkoxyalkoxyalkyl, C2-C 8 alkylthioalkyl, C2-C 8 alkylsul
  • each R 22 is independently i-C ⁇ alkyl or i-C ⁇ haloalkyl.
  • Embodiment B A compound of Embodiment A wherein
  • X is CH
  • A is A-3 or A-5;
  • B 2 is C-3;
  • R 1 is phenyl, -W 1 (phenyl), -W ⁇ S-phenyl), -W 1 (S0 2 -phenyl), -W 2 (S0 2 CH 2 -phenyl) or -W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or -W 2 G; or Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci ⁇ C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C2-C 8 alkoxyalkyl, C 3 -C
  • R 2 is phenyl or -W 3 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or Ci-C 6 alkyl, Ci ⁇ C 6 haloalkyl, C 3 -C 8 cycloalkyl, Ci ⁇ C 6 alkoxy, i ⁇ C 6 alkylthio or Ci ⁇ C 6 alkylsulfonyl;
  • R 3 is hydroxy or -O M + ; or phenylsulfonyloxy optionally substituted on ring members with up to two substituents selected from R 21 ;
  • R 9 is CH 2 CH 3 ;
  • R 10 is H or CH 3 ;
  • W 1 is -CH 2 -;
  • W 3 is -CH 2 -;
  • G is G-13, G-14, G-15, G-16 or G-17;
  • each R 21 is independently halogen, nitro, i ⁇ C 6 alkyl, Ci ⁇ C 6 haloalkyl, Ci ⁇ C 6 alkoxy, C ⁇ -C6 haloalkoxy or i-C ⁇ alkylthio.
  • Embodiment C 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 phenyl, -W 1 (phenyl), -W ⁇ S-phenyl), -W 1 (S0 2 -phenyl), -W 2 (S0 2 CH 2 -phenyl) or -W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or -W 2 G; or Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci ⁇ C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 al
  • alkylcycloalkyl C4-C 10 alkoxycycloalkyl, C 3 -C ⁇ Q alkoxyalkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C ⁇ 2 alkylsulfinylalkyl or C 2 -C 8 alkylsulfonylalkyl;
  • W 1 is -CH 2 -;
  • 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 Ci ⁇ C 6 alkyl or C 3 -C 8 cycloalkyl;
  • R 1 and R 2 are taken together along with the atoms to which they are attached to make an unsubstituted 7-membered partially unsaturated ring;
  • R 3 is hydroxy or C 2 -C 8 alkylcarbonyloxy
  • R 9 is CH 2 CH 3 ;
  • R 10 is H or CH 3 ;
  • G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20;
  • R 21 is independently halogen, nitro, i ⁇ C 6 alkyl, Ci ⁇ C 6 haloalkyl, Ci ⁇ C 6 alkoxy, C ⁇ -C6 haloalkoxy or i-C ⁇ alkylthio.
  • Embodiment D A compound of Embodiment C wherein
  • A is A-l or A-3;
  • R 1 is phenyl, 2-fluorophenyl, 3 -fluorophenyl, 4-fluorophenyl, 2-chlorophenyl,
  • R 2 is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl,
  • each R 14 , R 15 , R 18 and R 19 is H or CH 3 ;
  • T is -CH 2 CH 2 -.
  • Embodiment E A compound of Embodiment D wherein
  • A is A-l
  • R 1 is phenyl, 4-ethylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl,
  • R 2 is phenyl, 3-chlorophenyl, or 2-methylphenyl
  • Embodiment F A compound of Embodiment C wherein
  • A is A-3;
  • R 1 is rc-Pr or -CH 2 CH 2 OCH 3 ;
  • R 2 is phenyl, 2-methylphenyl, 3-methylphenyl, 4-chlorophenyl, 3 -fluorophenyl or 3,5 difiuorophenyl;
  • R 3 is hydroxy
  • each R 14 , R 15 , R 18 and R 19 is H.
  • Embodiment G A compound of Embodiment C wherein
  • A is A-l ;
  • R 1 is -G or -W 2 G; C r C 6 alkyl, C 3 -C 8 cycloalkyl, or C 2 -C 8 alkoxyalkyl;
  • G is G- 19 or G-20;
  • R 2 is phenyl, 2-methylphenyl, 3-methylphenyl, 4-chlorophenyl, 3 -fluorophenyl or 3,5 difiuorophenyl;
  • R 3 is hydroxy
  • each R 14 , R 15 , R 18 and R 19 is H.
  • Embodiment H A compound of Embodiment C wherein
  • A is A-l ;
  • R 1 is ⁇ - ⁇ , c-hexyl, -CH 2 CH 2 OCH 3 or -CH 2 CH 2 CH 2 OCH 3 ;
  • R 2 is 3-thienyl or 2-thienyl
  • R 3 is hydroxy
  • each R 14 , R 15 , R 18 and R 19 is H.
  • Specific embodiments include a compound of Formula 1 selected from:
  • Specific embodiments also include a compound of Formula 1 selected from:
  • te is a compound of Formula 1 selected from:
  • Embodiments of the present invention as described in the Summary of the Invention also include (where Formula IQ from the Summary of the Invention as used in the following Embodiments includes N-oxides and salts thereof):
  • Embodiment IQ A compound of Formula IQ wherein A' is A'-l , A'-3 or A'-5.
  • Embodiment 2Q A compound of Embodiment 2Q wherein A' is A'-l or A'-3.
  • Embodiment 3Q A compound of Embodiment 3Q wherein A' is A'-l .
  • Embodiment 4Q A compound of Embodiment 4Q wherein A' is A'-3.
  • Embodiment 5Q A compound of Formula IQ or any one of Embodiments IQ through
  • Embodiment 6Q A compound of Formula IQ or any one of Embodiments IQ through
  • Embodiment 7Q A compound of Formula IQ or any one of Embodiments IQ through 6Q wherein B 2 is C-3.
  • Embodiment 8Q A compound of Formula IQ or any one of Embodiments IQ through
  • Embodiment 9Q A compound of Formula IQ or any one of Embodiments IQ through 8Q wherein B 3 is C-l .
  • Embodiment 10Q A compound of Formula IQ or any one of Embodiments IQ
  • Embodiment 1 IQ A compound of Formula IQ or any one of Embodiments IQ
  • R 1 is phenyl, -W 1 (phenyl), -W ⁇ S-phenyl), -W 1 (S0 2 - phenyl), -W 2 (S0 2 CH 2 -phenyl) or -W 2 (SCH 2 -phenyl), each optionally substituted on ring members with up to five substituents selected from R 21 ; or -G or -W 2 G; or C r C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C r C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12
  • alkylcycloalkylalkyl C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 3 -CIQ alkoxyalkenyl, C4-C10 alkylcycloalkyl, C4-C 10
  • alkoxycycloalkyl C 3 -C IQ alkoxyalkoxyalkyl, C2-C 8 alkylthioalkyl, C2-C12 alkylsulfinylalkyl or C2-C 8 alkylsulfonylalkyl.
  • Embodiment 12Q A compound of Embodiment HQ wherein R 1 is phenyl or
  • -W 1 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or -G or -W 2 G; or Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci ⁇ C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C2-C 8 alkoxyalkyl C 3 -C IQ alkoxyalkenyl, C4-C 10
  • alkylcycloalkyl or C4-C10 alkoxycycloalkyl are examples of alkylcycloalkyl or C4-C10 alkoxycycloalkyl.
  • Embodiment 13Q A compound of Embodiment 12Q wherein R 1 is phenyl,
  • Embodiment 14Q A compound of Embodiment 13Q wherein R 1 is phenyl, 4- ethylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl.
  • Embodiment 15Q A compound of Embodiment 14Q wherein R 1 is phenyl,
  • Embodiment 16Q A compound of Embodiment 15Q wherein R 1 is phenyl.
  • Embodiment 17Q A compound of Embodiment 14Q wherein R 1 is
  • Embodiment 18Q A compound of Embodiment 14Q wherein R 1 is 5-chloro-2- methylphenyl.
  • Embodiment 19Q A compound of Formula 1Q or any one of Embodiments 1 through
  • Embodiment 20Q A compound of Embodiment HQ wherein R 1 is -G or -W 2 G; C ⁇ - C 6 alkyl, C 3 -C 8 cycloalkyl, or C 2 -C 8 alkoxyalkyl.
  • Embodiment 21Q A compound of Embodiment 20Q wherein R 1 is -G or -W 2 G.
  • Embodiment 22Q A compound of Embodiment 20Q wherein R 1 is C ⁇ -C6 alkyl
  • Embodiment 23 Q A compound of Embodiment 22Q wherein R 1 is n-Vr, z ' -Pr, n- u, c-hexyl, -CH 2 CH 2 OCH 3 , -CH 2 CH 2 CH 2 OCH 3 or -CH 2 CH 2 OCH 2 CH 3 .
  • Embodiment 24Q A compound of Embodiment 23 Q wherein R 1 is n-Vr, c-hexyl, -CH 2 CH 2 OCH 3 or -CH 2 CH 2 CH 2 OCH 3 .
  • Embodiment 25 Q A compound of Formula IQ or any one of Embodiments IQ through 12Q wherein W 1 is i ⁇ C 6 alkylene.
  • Embodiment 26Q A compound of Embodiment 25Q wherein W 1 is -CH 2 -.
  • Embodiment 27Q A compound of Formula IQ or any one of Embodiments IQ
  • Embodiment 28Q A compound of Formula IQ or any one of Embodiments
  • Embodiment IQ through 27Q 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; or Ci ⁇ C 6 alkyl or C 3 -C 8 cycloalkyl.
  • Embodiment 29Q A compound of Embodiment 28Q wherein R 2 is phenyl optionally substituted on ring members with up to two substituents selected from R 21 ; or
  • Ci-Cfr alkyl, C 3 -C 8 cycloalkyl is Ci-Cfr alkyl, C 3 -C 8 cycloalkyl.
  • Embodiment 30Q A compound of Embodiment 29Q wherein R 2 is phenyl,
  • Embodiment 31Q A compound of Embodiment 30Q wherein R 2 is phenyl.
  • Embodiment 32Q A compound of Formula IQ or any one of Embodiments IQ
  • R 2 is other than phenyl.
  • Embodiment 33Q A compound of Embodiment 32Q wherein R 2 is 3-thienyl or 2- thienyl.
  • Embodiment 34Q A compound of Embodiment 33Q wherein R 2 is n-propyl, n-butyl, or cyclopropyl.
  • Embodiment 35Q A compound of Formula IQ or any one of Embodiments IQ
  • Embodiment 36Q A compound of Formula IQ or any one of Embodiments IQ
  • R 9 is C r C 6 alkyl.
  • Embodiment 37Q A compound of Formula IQ or any one of Embodiments IQ or
  • Embodiment 38Q A compound of Formula IQ or any one of Embodiments IQ or HQ through 36Q wherein R 10 is H, halogen or C r C 6 alkyl.
  • Embodiment 39Q A compound of Embodiment 38Q wherein R 10 is H or CH 3 .
  • Embodiment 40Q A compound of Formula IQ or any one of Embodiments IQ
  • 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 i-C ⁇ alkyl.
  • Embodiment 41Q A compound of Embodiment 40Q 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 42Q A compound of Embodiment 41Q 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 43 Q A compound of Formula 1Q or any one of Embodiments 1Q
  • each R 15 and R 19 is is H or CH 3 .
  • Embodiment 44Q A compound of Embodiment 43Q wherein independently each R 15 and R 19 is H.
  • Embodiment 45 Q A compound of Formula 1Q or any one of Embodiments 1Q
  • Embodiment 46Q A compound of Embodiment 45 Q wherein R 20 is H or CH 3 .
  • Embodiment 47Q A compound of Formula 1Q or any one of Embodiments 1Q, 2Q,
  • Embodiment 48Q A compound of Embodiment 47Q wherein T is -CH 2 CH 2 -.
  • Embodiment 49Q A compound of Formula 1Q or any one of Embodiments 1Q
  • G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20 (as depicted in Embodiment 79).
  • Embodiment 50Q A compound of Embodiment 49Q wherein when R 1 is G, then G is G-19 or G-20.
  • Embodiment 51Q A compound of Embodiment 50Q wherein when R 1 is G, then G is G-19.
  • Embodiment 52Q A compound of Embodiment 50Q wherein when R 1 is G, then G is G-20.
  • Embodiment 53Q A compound of Embodiment 49Q wherein when R 2 is G, then G is G-2, G-3 or G-15.
  • Embodiment 54Q A compound of Embodiment 53Q wherein when R 2 is G, then G is G-2.
  • Embodiment 55Q A compound of Embodiment 53Q wherein when R 2 is G, then G is G-3.
  • Embodiment 56Q A compound of Formula 1Q or any one of Embodiments 1Q
  • each R 21 is independently halogen, nitro, i ⁇ C 6 alkyl, C j - haloalkyl, i-C ⁇ alkoxy, Ci-C ⁇ haloalkoxy or i-C ⁇ alkylthio.
  • Embodiment 57Q A compound of Embodiment 56Q wherein each R 21 is
  • Embodiment 58Q A compound of Formula 1Q or any one of Embodiments 1Q
  • each R 22 is independently i-C ⁇ alkyl or i-C ⁇ haloalkyl.
  • Embodiment 59Q A compound of Embodiment 58Q wherein each R 22 is
  • Embodiment 60Q A compound of Formula 1 or any one of Embodiments 1Q through
  • R 1 is phenyl optionally substituted with up to five substituents selected from R 21 ; or -G or -W 2 G; C 4 -C 10 alkylcycloalkyl, C 4 -C 10
  • alkylthioalkyl C2-Cg alkylsulfinylalkyl, C2-Cg alkylsulfonylalkyl, C2-Cg haloalkoxyalkyl, C3-C10 dialkoxyalkyl or C3-C10 alkoxycarbonylalkyl or C2-Cg haloalkoxycarbonyl.
  • Embodiment 61Q A compound of Embodiment 60Q wherein R 1 is phenyl,
  • Embodiment 62Q A compound of Embodiment 61Q wherein R 1 is 4-methoxyphenyl.
  • Embodiment 63 Q A compound of Embodiment 61Q wherein R 1 is
  • Embodiment 64Q A compound of Embodiment 61Q wherein R 1 is
  • Embodiment 65Q A compound of Embodiment 60Q wherein R 1 is -G or -W 2 G.
  • Embodiment 66Q A compound of Embodiment 65Q wherein R 1 is -W 2 G.
  • Embodiment 67Q A compound of Embodiment 65Q or 66Q wherein G is G-9.
  • Embodiment 68Q A compound of Embodiment 67Q wherein W 2 is -CH 2 - and G is tetrahydrofuran-2-yl.
  • Embodiment 69Q A compound of Embodiment 68Q wherein R 1 is
  • Embodiment 70Q A compound of Embodiment 60Q wherein R 1 is
  • Embodiment 71Q A compound of Embodiment 70Q wherein R 1 is
  • Embodiment 72Q A compound of Embodiment 71Q wherein R 1 is
  • Embodiment 73 Q A compound of Embodiment 72Q wherein R 1 is
  • Embodiment 74Q A compound of Embodiment 72Q wherein R 1 is
  • Embodiment 75 Q A compound of Embodiment 72Q wherein R 1 is a mixture of
  • Embodiment 76Q A compound of Embodiment 70Q wherein R 1 is -CH2CH2SCH3, -CH 2 CH 2 SCH 2 CH 3 , -CH 2 CH 2 SOCH 3 , -CH 2 CH 2 SOCH 2 CH 3 ,
  • Embodiment 77Q A compound of Embodiment 76Q wherein R 1 is -CH 2 CH 2 SCH 3 ,
  • Embodiment 78Q A compound of Embodiment 77Q wherein R 1 is
  • Embodiment 79Q A compound of Embodiment 23 Q wherein R 1 is n-Pr.
  • Embodiment 80Q A compound of Embodiment 23Q wherein R 1 is -CH 2 CH 2 OCH 3 .
  • Embodiment 81Q A compound of Embodiment 28Q wherein R 2 is phenyl or
  • Embodiment 82Q A compound of Embodiment 81Q wherein R 2 is -G.
  • Embodiment 83Q A compound of Embodiment 80Q wherein R 2 is 3-thienyl, 2-thienyl or 3-pyridinyl.
  • Embodiment 84Q A compound of Embodiment 83Q wherein R 2 is 3-pyridinyl.
  • Embodiment 85Q A compound of Embodiment 81Q wherein R 2 is phenyl or
  • Embodiment 86Q A compound of Embodiment 60Q whereinR 1 is phenyl substituted with up to two substituents selected from Ci-C 6 alkoxy; or -W 2 G; or Ci-C 6 alkyl, C 2 -C 8 alkoxyalkyl, C4-C10 alkoxycycloalkyl or C 3 -C ⁇ o
  • 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 phenyl, -W 1 (phenyl),
  • Embodiment 2R A compound of Embodiment 1R wherein R 1 is phenyl or
  • -W 1 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or -G or -W 2 G; or Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci ⁇ C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, 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 -C 10
  • alkylcycloalkyl or C4-C10 alkoxycycloalkyl are examples of alkylcycloalkyl or C4-C10 alkoxycycloalkyl.
  • Embodiment 3R A compound of Embodiment 2R wherein R 1 is phenyl,
  • Embodiment 4R A compound of Embodiment 3R wherein R 1 is phenyl, 4- ethylphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl.
  • Embodiment 5R A compound of Embodiment 4R wherein R 1 is phenyl,
  • Embodiment 6R A compound of Embodiment 5R wherein R 1 is phenyl.
  • Embodiment 7R A compound of Embodiment 4R wherein R 1 is
  • Embodiment 8R A compound of Embodiment 4R wherein R 1 is 5-chloro-2- methylphenyl.
  • Embodiment 9R A compound of Formula IR or any one of Embodiments IR through
  • Embodiment 10R A compound of Formula IR or any one of Embodiments IR and 2R R wherein R 1 is -G or -W 2 G; C r C 6 alkyl, C 3 -C 8 cycloalkyl, or C 2 -C 8 alkoxyalkyl.
  • Embodiment 1 IR.
  • Embodiment 12R A compound of Embodiment 10R wherein R 1 is Ci-C ⁇ alkyl, C 3 -C 8 cycloalkyl, or C 2 -C 8 alkoxyalkyl.
  • Embodiment 13R A compound of Embodiment 12R wherein R 1 is n-Vr, z ' -Pr, n- u, c-hexyl, -CH 2 CH 2 OCH 3 , -CH 2 CH 2 CH 2 OCH 3 or -CH 2 CH 2 OCH 2 CH 3 .
  • Embodiment 14R A compound of Embodiment 13R wherein R 1 is n-Vr, c-hexyl,
  • Embodiment 15R A compound of Formula IR or any one of Embodiments IR and 2R wherein W 1 is i ⁇ C 6 alkylene.
  • Embodiment 16R A compound of Embodiment 15R wherein W 1 is -CH 2 -.
  • Embodiment 17R A compound of Formula IR or any one of Embodiments IR, 2R
  • Embodiment 18R A compound of Formula 1R or any one of Embodiments
  • Embodiment 1R through 17R 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; or Ci ⁇ C 6 alkyl or C 3 -C 8 cycloalkyl.
  • Embodiment 19R A compound of Embodiment 18R wherein R 2 is phenyl optionally substituted on ring members with up to two substituents selected from R 21 ; or
  • Embodiment 20R A compound of Embodiment 19R wherein R 2 is phenyl,
  • Embodiment 21R A compound of Embodiment 20R wherein R 2 is phenyl.
  • Embodiment 22R A compound of Formula 1R or any one of Embodiments 1R
  • R 2 is other than phenyl
  • Embodiment 23R A compound of Embodiment 22R wherein R 2 is 3-thienyl or
  • Embodiment 24R A compound of Embodiment 23R wherein R 2 is n-propyl, n-butyl, or cyclopropyl.
  • Embodiment 25R A compound of Formula 1R or any one of Embodiments 1R
  • Embodiment 26R A compound of Formula 1R or any one of Embodiments 1R
  • G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20 (as depicted in Embodiment 79).
  • Embodiment 27R A compound of Embodiment 26R wherein when R 1 is G, then G is G-19 or G-20.
  • Embodiment 28R A compound of Embodiment 27R wherein when R 1 is G, then G is G-19.
  • Embodiment 29R A compound of Embodiment 28R wherein when R 1 is G, then G is G-20.
  • Embodiment 3 OR. A compound of Embodiment 26R wherein when R 2 is G, then G is G-2, G-3 or G-15.
  • Embodiment 31R A compound of Embodiment 3 OR wherein when R 2 is G, then G is G-2.
  • Embodiment 32R A compound of Embodiment 31R wherein when R 2 is G, then G is G-3.
  • Embodiment 33R A compound of Formula 1R or any one of Embodiments 1R
  • each R 21 is independently halogen, nitro, i ⁇ C 6 alkyl, C j - haloalkyl, i-C ⁇ alkoxy, Ci-C ⁇ haloalkoxy or i-C ⁇ alkylthio.
  • Embodiment 34R A compound of Embodiment 33R wherein each R 21 is
  • Embodiment 35R A compound of Formula IR or any one of Embodiments IR
  • each R 22 is independently i-C ⁇ alkyl or i-C ⁇ haloalkyl.
  • Embodiment 36R A compound of Embodiment 35R wherein each R 22 is
  • Embodiment 37R A compound of Formula 1 or Embodiment IR wherein R 1 is phenyl optionally substituted with up to five substituents selected from R 21 ; or -G or
  • Embodiment 38R A compound of Embodiment 37R wherein R 1 is phenyl,
  • Embodiment 39R A compound of Embodiment 38R wherein R 1 is 4-methoxyphenyl.
  • Embodiment 40R A compound of Embodiment 38R wherein R 1 is
  • Embodiment 41R A compound of Embodiment 38R wherein R 1 is
  • Embodiment 42R A compound of Embodiment 37R wherein R 1 is -G or -W 2 G.
  • Embodiment 43R A compound of Embodiment 42R wherein R 1 is -W 2 G.
  • Embodiment 44R A compound of Embodiment 43R wherein G is G-9.
  • Embodiment 45R A compound of Embodiment 43R wherein W 2 is -CH 2 - and G is tetrahydrofuran-2-yl.
  • Embodiment 46R A compound of Embodiment 45R wherein R 1 is
  • Embodiment 47R A compound of Embodiment 37R wherein R 1 is
  • Embodiment 48R A compound of Embodiment 47R wherein R 1 is
  • Embodiment 49R A compound of Embodiment 48R wherein R 1 is
  • Embodiment 5 OR.
  • Embodiment 51R A compound of Embodiment 49R wherein R 1 is
  • Embodiment 52R A compound of Embodiment 48R wherein R 1 is a mixture of
  • Embodiment 53R A compound of Embodiment 47R wherein R 1 is -CH 2 CH 2 SCH 3 ,
  • Embodiment 54R A compound of Embodiment 53R wherein R 1 is -CH 2 CH 2 SCH 3 ,
  • Embodiment 55R A compound of Embodiment 54R wherein R 1 is
  • Embodiment 56R A compound of Embodiment 13R wherein R 1 is n-Pr.
  • Embodiment 57R A compound of Embodiment 13R wherein R 1 is -CH 2 CH 2 OCH 3 .
  • Embodiment 58R A compound of Embodiment 18R wherein R 2 is phenyl or
  • Embodiment 59R A compound of Embodiment 58R wherein R 2 is -G.
  • Embodiment 60R A compound of Embodiment 48R wherein R 2 is 3-thienyl, 2-thienyl or 3-pyridinyl.
  • Embodiment 61R A compound of Embodiment 60R wherein R 2 is 3-pyridinyl.
  • Embodiment 62R A compound of Embodiment 61R wherein R 2 is phenyl or
  • Embodiment 63R A compound of Embodiment 58R wherein R 2 is phenyl, 3-pyridyl, 3,5-dimethylphenyl, 3,5-difluorophenyl, 3-methylphenyl, 3-methoxyphenyl.
  • Embodiment 64R A compound of Embodiment 2R wherein R 1 is phenyl optionally substituted with up to two substituents selected from R 21 ; or -W 2 G; or Ci-C 6 alkyl, C 2 -Cg alkoxyalkyl, C4-C10 alkoxycycloalkyl.
  • Embodiment 65R A compound of Embodiment 37R wherein R 1 is phenyl substituted with up to two substituents selected from Ci-C 6 alkoxy; or -W 2 G; or Ci-C 6 alkyl, C 2 -Cg alkoxyalkyl, C4-C10 alkoxycycloalkyl or C 3 -C ⁇ o
  • Embodiment 66R A compound of Embodiment 65R wherein R 1 is
  • 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 R 1 is phenyl, -W 1 (phenyl),
  • Embodiment 2S A compound of Embodiment IS wherein R 1 is phenyl or
  • -W 1 (phenyl), each optionally substituted on ring members with up to two substituents selected from R 21 ; or -G or -W 2 G; or Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Ci ⁇ C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 3 -C 8 cycloalkyl, C 4 -C 10 cycloalkylalkyl, C 5 -C 12 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 3 -C 8 halocycloalkenyl, C 2 -C 8 alkoxyalkyl, C 3 -C ⁇ o alkoxyalkenyl, C4-C10 alkylcycloalkyl, C4-C10 alkoxycycloalkyl.
  • Embodiment 3S A compound of Embodiment 2S wherein R 1 is phenyl,
  • Embodiment 4S A compound of Embodiment 3S wherein R 1 is phenyl,
  • Embodiment 5S A compound of Embodiment 4S wherein R 1 is phenyl,
  • Embodiment 6S A compound of Embodiment 5S wherein R 1 is phenyl.
  • Embodiment 7S A compound of Embodiment 4S wherein R 1 is 3,4-dimethoxyphenyl.
  • Embodiment 8S A compound of Embodiment 4S wherein R 1 is 5-chloro-2- methylphenyl.
  • Embodiment 9S A compound of Formula IS or any one of Embodiments IS through 8S wherein R 1 is other than phenyl.
  • Embodiment 10S A compound of Formula IS or any one of Embodiments IS and 2S wherein R 1 is -G or -W 2 G; i ⁇ C 6 alkyl, C 3 -C 8 cycloalkyl, or C 2 -C 8 alkoxyalkyl.
  • Embodiment 1 IS.
  • Embodiment 12S A compound of Embodiment 10S wherein R 1 is i ⁇ C 6 alkyl, C 3 -C 8 cycloalkyl, or C 2 -C 8 alkoxyalkyl.
  • Embodiment 13S A compound of Embodiment 12S wherein R 1 is n-Vr, z ' -Pr, n- u, c-hexyl, -CH 2 CH 2 OCH 3 , -CH 2 CH 2 CH 2 OCH 3 or -CH 2 CH 2 OCH 2 CH 3 .
  • Embodiment 14S A compound of Embodiment 13S wherein R 1 is n-Vr, c-hexyl,
  • Embodiment 15S A compound of Formula IS or any one of Embodiments IS and 2S wherein W 1 is i ⁇ C 6 alkylene.
  • Embodiment 16S A compound of Embodiment 15S wherein W 1 is -CH 2 -.
  • Embodiment 17S A compound of Formula IS or any one of Embodiments IS, 2S 10S and 1 IS wherein W 2 is -CH 2 -.
  • Embodiment 18S A compound of Formula IS or any one of Embodiments
  • Embodiment IS through 17S 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; or Ci ⁇ C 6 alkyl or C 3 -C 8 cycloalkyl.
  • Embodiment 19S A compound of Embodiment 18S wherein R 2 is phenyl optionally substituted on ring members with up to two substituents selected from R 21 ; or
  • Ci-Cfr alkyl, C 3 -C 8 cycloalkyl is Ci-Cfr alkyl, C 3 -C 8 cycloalkyl.
  • Embodiment 20S A compound of Embodiment 19S wherein R 2 is phenyl,
  • Embodiment 2 IS.
  • Embodiment 22S A compound of Formula IS or any one of Embodiments IS through
  • Embodiment 23S A compound of Embodiment 22S wherein R 2 is 3-thienyl or
  • Embodiment 24S A compound of Embodiment 23S wherein R 2 is n-propyl, n-butyl, or cyclopropyl.
  • Embodiment 25 S A compound of Formula IS or any one of Embodiments IS through
  • Embodiment 26S A compound of Formula IS or any one of Embodiments IS through 25S wherein G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20 (as depicted in
  • Embodiment 27S A compound of Embodiment 26S wherein when R 1 is G, then G is G-19 or G-20.
  • Embodiment 28S A compound of Embodiment 27S wherein when R 1 is G, then G is G-19.
  • Embodiment 29S A compound of Embodiment 28S wherein when R 1 is G, then G is G-20.
  • Embodiment 30S A compound of Embodiment 26S wherein when R 2 is G, then G is G-2, G-3 or G-15.
  • Embodiment 3 I A compound of Embodiment 30S wherein when R 2 is G, then G is G-2.
  • Embodiment 32S A compound of Embodiment 3 I S wherein when R 2 is G, then G is G-3.
  • Embodiment 33 S A compound of Formula IS or any one of Embodiments I S through
  • each R 21 is independently halogen, nitro, i ⁇ C 6 alkyl, Ci ⁇ C 6 haloalkyl, i-C ⁇ alkoxy, Ci-C ⁇ haloalkoxy or i-C ⁇ alkylthio.
  • Embodiment 34S A compound of Embodiment 33S wherein each R 21 is
  • Embodiment 35 S A compound of Formula IS or any one of Embodiments I S through
  • each R 22 is independently i-C ⁇ alkyl or i-C ⁇ haloalkyl.
  • Embodiment 36S A compound of Embodiment 35S wherein each R 22 is
  • Embodiment 37S A compound of Formula IS or any on of Embodiments I S through
  • R 23 is an optionally substituted carbon moiety, R 23 is C j -C ⁇ alkyl; or phenyl or benzyl optionally substituted with halogen, nitro, cyano or hydroxy on ring members.
  • Embodiment 38S A compound of Embodiment 37S wherein when R 23 is an
  • R 23 is Ci -Ci Q alkyl; or phenyl or benzyl optionally substituted with halogen or nitro on ring members.
  • Embodiment 39S A compound of Embodiment 38S wherein when R 23 is an
  • R 23 is i ⁇ C 6 alkyl; or benzyl optionally substituted with halogen or nitro on ring members.
  • Embodiment 40S A compound of Embodiment 39S wherein when R 23 is an
  • R 23 is i ⁇ C 6 alkyl; or unsubsituted benzyl.
  • R 23 is i ⁇ C 6 alkyl.
  • Embodiment 42S A compound of Embodiment 41 S wherein when R 23 is an
  • R 23 is unsubstituted benzyl.
  • Embodiment 43S A compound of Embodiment 42S wherein when R 23 is an
  • R 23 is ethyl, n-propyl, n-butyl or /-propyl.
  • Embodiment 44S A compound of Embodiment 43S wherein when R 23 is an optionally substituted carbon moiety, R 23 is ethyl, n-propyl or /-propyl.
  • Embodiment 45S A compound of Embodiment 44S wherein when R 23 is an
  • R 23 is ethyl
  • Embodiment 46S A compound of Formula 1 or any one of Embodiments IS or 2S wherein R 1 is phenyl optionally substituted with up to five substituents selected from R 21 ; or -G or -W 2 G; C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 2 -C 8 alkoxyalkyl, C 4 -C 10 alkoxycycloalkyl, C 2 -C 8 alkylthioalkyl, C 2 -C 8 alkylsulfinylalkyl, C 2 -Cg alkylsulfonylalkyl, C 2 -Cg haloalkoxyalkyl, C 3 -CI Q dialkoxyalkyl or C 3 -C I Q alkoxycarbonylalkyl or C 2 -Cg haloalkoxycarbonyl.
  • Embodiment 47S A compound of Embodiment 46S wherein R 1 is phenyl,
  • Embodiment 48S A compound of Embodiment 47S wherein R 1 is 4-methoxyphenyl.
  • Embodiment 49S A compound of Embodiment 47S wherein R 1 is
  • Embodiment 50S A compound of Embodiment 47S wherein R 1 is
  • Embodiment 5 IS.
  • Embodiment 52S A compound of Embodiment 5 IS wherein R 1 is -W 2 G.
  • Embodiment 53S A compound of Embodiment 52S wherein G is G-9.
  • Embodiment 54S A compound of Embodiment 53S wherein W 2 is -CH 2 - and G is tetrahydrofuran-2-yl.
  • Embodiment 55S A compound of any one of Embodiments 51S through 54S wherein R 1 is -CH 2 (tetrahydrofuran-2-yl).
  • Embodiment 56S A compound of Embodiment 46S wherein R 1 is
  • Embodiment 57S A compound of Embodiment 56S wherein R 1 is
  • Embodiment 58S A compound of Embodiment 57S wherein R 1 is
  • Embodiment 59S A compound of Embodiment 58S wherein R 1 is
  • Embodiment 60S A compound of Embodiment 59S wherein R 1 is
  • Embodiment 61S A compound of Embodiment 57S wherein R 1 is a mixture of
  • Embodiment 62S A compound of Embodiment 56S wherein R 1 is -CH2CH2SCH3,
  • Embodiment 63 S. A compound of Embodiment 62S wherein R 1 is -CH 2 CH 2 SCH 3 ,
  • Embodiment 64S A compound of Embodiment 63 S wherein R 1 is
  • Embodiment 65 S. A compound of Embodiment 13S wherein R 1 is n-Pr.
  • Embodiment 66S A compound of Embodiment 13S wherein R 1 is -CH 2 CH 2 OCH 3 .
  • Embodiment 67S A compound of Embodiment 18S wherein R 2 is phenyl or
  • Embodiment 68S A compound of Embodiment 67S wherein R 2 is -G.
  • Embodiment 69S A compound of Embodiment 68S wherein R 2 is 3-thienyl, 2-thienyl or 3-pyridinyl.
  • Embodiment 70S A compound of Embodiment 69S wherein R 2 is 3-pyridinyl.
  • Embodiment 7 IS.

Abstract

Cette invention concerne des composés de Formule (1), comprenant tous leurs stéréoisomères, N-oxydes, et sels, (Formula (1)). Dans la Formule (1), X est CH ou N ; Y est C(O) ou S(O)2 ; à condition que, quand Y est S(O)2, alors X est CH ; A est un radical choisi dans le groupe constitué par les Formules (A-1), (A-2), (A-3), (A-4), (A-5), (A-6) et (A-7) ; 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. Des compositions contenant les composés de Formule (1) sont également décrites, ainsi que des procédés pour lutter contre la végétation indésirable, lesdits composés comprenant la mise en contact de la végétation indésirable ou de son environnement avec une quantité efficace d'un composé ou d'une composition selon l'invention.
PCT/US2011/027737 2009-09-09 2011-03-09 Oxo-hétérocycles et sulfono-hétérocycles bis-azotés herbicides WO2012033548A2 (fr)

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TW101105776A TWI549943B (zh) 2011-03-09 2012-02-22 除草之含側氧與磺酸基(sulfono)雙氮雜環
ARP120100774A AR085645A1 (es) 2011-03-09 2012-03-09 Derivados de pirimidinona herbicidas
UY33944A UY33944A (es) 2009-09-09 2012-03-09 Oxo y sulfono heterociclos herbicidas que contienen bis-hidrógeno

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USPCT/US1000/047944 2010-09-07
PCT/US2010/047944 WO2011031658A1 (fr) 2009-09-09 2010-09-07 Dérivés herbicides de pyrimidone
ARP20100103305 2010-09-09
ARP100103305 AR078354A1 (es) 2009-09-09 2010-09-09 Heterociclos herbicidas oxo y sulfono bis-nitrogenados

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WO2014100525A2 (fr) 2012-12-21 2014-06-26 Pioneer Hi-Bred International, Inc. Compositions et procédés pour la conjugaison d'analogues d'auxine
WO2014153242A1 (fr) 2013-03-14 2014-09-25 Pioneer Hi-Bred International, Inc. Compositions ayant une activité de décarboxylase de dicamba et leurs procédés d'utilisation
WO2014153234A1 (fr) 2013-03-14 2014-09-25 Pioneer Hi-Bred International, Inc. Compositions ayant une activité de dicamba décarboxylase et procédés d'utilisation
CN104557739A (zh) * 2013-10-25 2015-04-29 华中师范大学 三酮类化合物及其制备方法和应用
WO2016084922A1 (fr) * 2014-11-28 2016-06-02 塩野義製薬株式会社 Dérivé 1,2,4-triazine et composition pharmaceutique correspondante
CN112552303A (zh) * 2020-12-14 2021-03-26 承德医学院 嘧啶酮并二氮杂卓类化合物及其盐、其制备方法及医药用途
US11072608B2 (en) * 2014-12-17 2021-07-27 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014100525A2 (fr) 2012-12-21 2014-06-26 Pioneer Hi-Bred International, Inc. Compositions et procédés pour la conjugaison d'analogues d'auxine
WO2014153242A1 (fr) 2013-03-14 2014-09-25 Pioneer Hi-Bred International, Inc. Compositions ayant une activité de décarboxylase de dicamba et leurs procédés d'utilisation
WO2014153234A1 (fr) 2013-03-14 2014-09-25 Pioneer Hi-Bred International, Inc. Compositions ayant une activité de dicamba décarboxylase et procédés d'utilisation
CN104557739A (zh) * 2013-10-25 2015-04-29 华中师范大学 三酮类化合物及其制备方法和应用
CN104557739B (zh) * 2013-10-25 2016-11-09 山东先达农化股份有限公司 三酮类化合物及其制备方法和应用
US9771334B2 (en) 2013-10-25 2017-09-26 Shandong Cynda Chemical Co., Ltd. Triketone compound and preparation method and use thereof
WO2016084922A1 (fr) * 2014-11-28 2016-06-02 塩野義製薬株式会社 Dérivé 1,2,4-triazine et composition pharmaceutique correspondante
US11072608B2 (en) * 2014-12-17 2021-07-27 Syngenta Participations Ag Pesticidally active heterocyclic derivatives with sulphur containing substituents
CN112552303A (zh) * 2020-12-14 2021-03-26 承德医学院 嘧啶酮并二氮杂卓类化合物及其盐、其制备方法及医药用途
CN112552303B (zh) * 2020-12-14 2021-11-30 承德医学院 嘧啶酮并二氮杂卓类化合物及其盐、其制备方法及医药用途

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