EP0922032A1 - Pyridinylcetones et pyrazolylphenylcetones herbicides - Google Patents

Pyridinylcetones et pyrazolylphenylcetones herbicides

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Publication number
EP0922032A1
EP0922032A1 EP97928809A EP97928809A EP0922032A1 EP 0922032 A1 EP0922032 A1 EP 0922032A1 EP 97928809 A EP97928809 A EP 97928809A EP 97928809 A EP97928809 A EP 97928809A EP 0922032 A1 EP0922032 A1 EP 0922032A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
halogen
compound
cyano
nitro
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP97928809A
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German (de)
English (en)
Inventor
Kanu Maganbhai Patel
Morris Padgett Rorer
Chi-Ping Tseng
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of EP0922032A1 publication Critical patent/EP0922032A1/fr
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/72—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
    • A01N43/74—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 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/24—Radicals substituted by oxygen atoms
    • 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
    • C07D401/10—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 linked by a carbon chain containing aromatic rings

Definitions

  • This invention relates to certain phenyl ketones, their JV-oxides, agriculturally suitable 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, corn (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 which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
  • WO 96/26200 discloses pyrazoles of Formula i as herbicides:
  • Q represents a cyclohexane- 1,3-dione ring
  • L and M are hydrogen, C r C 6 alkyl, C ⁇ -C 4 alkoxy, halogen or nitro;
  • Z represents a five to six-membered heterocyclic saturated or unsaturated group.
  • This invention is directed to compounds of Formula I including all geometric and stereoisomers, TV-oxides, and agriculturally suitable salts thereof, agricultural compositions containing them and their use for controlling undesirable vegetation:
  • A is a five- to ten-membered monocyclic or fused bicyclic ring system, which may be fully aromatic or partially saturated, containing 1 to 4 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that each heterocyclic ring system contains no more than 2 oxygens and no more than 2 sulfurs, and each ring system is optionally substituted with one to three R 2 , provided that when a nitrogen atom of a heterocyclic ring is substituted with R 2 , then R 2 is other than halogen; each R 1 is independently H, C ⁇ -C 6 alkyl, C r C 6 haloalkyl, C r C 6 alkoxy, C r C 6 haloalkoxy, halogen, cyano, nitro, -(Y) r S(O) n R 15 or -(Y) t -C(O)R 15 ;
  • W is N or CH
  • Y is O or NR 12 ;
  • R 2 is C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C r C 6 alkoxy, C C 6 haloalkoxy, C 3 -C 6 alkenyloxy, C ⁇ -C ⁇ alkynyloxy, mercapto, C j -C 6 alkylthio, C j -C 3 haloalkylthio, C 3 -C 6 alkenylthio, C 3 -C 6 haloalkenylthio, C 3 -C 6 alkynylthio, C 2 -C 5 alkoxyalkylthio, C 3 -C 5 acetylalkylthio, C 3 -C 6 alkoxycarbonylalkylthio, C2-C 4 cyanoal
  • R 2 is phenyl or benzylthio, each optionally substituted on the phenyl ring with C ] -C 3 alkyl, C r C 3 haloalkyl, C ⁇ -C 3 alkoxy, C j -C 3 haloalkoxy, 1-2 halogen, cyano or nitro;
  • R 3 is OR 14 , SH, C C 6 alkylthio, C,-C 6 haloalkylthio, C r C 6 alkylsulfinyl, C r C 6 haloalkylsulfinyl, C j -Cg alkylsulfonyl, C j -C 6 haloalkylsulfonyl, halogen or
  • R 3 is phenylthio, phenylsulfonyl or -SCH 2 C(O)Ph, each optionally substituted with C ] -C 3 alkyl, halogen, cyano or nitro; each R 4 is independently C r C 3 alkyl, C j -C 3 alkoxy, C j -C 3 alkylthio or halogen; or when two R 4 are attached to the same carbon atom, then said R 4 pair can be taken together to form -OCH 2 CH 2 O-, -OCH 2 CH 2 CH 2 O-, -SCH 2 CH 2 S- or -SCH 2 CH 2 CH 2 S-, each group optionally substituted with 1-4 CH 3 ;
  • R 5 is OR 14 , SH, C r C 6 alkylthio, C r C 6 haloalkylthio, C r C 6 alkylsulfinyl, C,-C 6 haloalkylsulfinyl, C r C 6 alkylsulfonyl, C j -C 6 haloalkylsulfonyl, halogen or NR 12 R 13 ; or R 5 is phenylthio, phenylsulfonyl or -SCH 2 C(O)Ph, each optionally substituted with C ⁇ -C 3 alkyl, halogen, cyano or nitro;
  • R 6 is H, C,-C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or
  • R 6 is phenyl or benzyl, each optionally substituted on the phenyl ring with Cj-C 3 alkyl, halogen, cyano or nitro;
  • R 7 is H, C ] -C 6 alkyl, C ⁇ -C 6 haloalkyl, C r C 6 alkoxy, C r C 6 haloalkoxy, halogen, cyano or nitro;
  • R8 is H, C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 cycloalkyl or C 3 -C 6 halocycloalkyl;
  • R 9 is H, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 haloalkoxy carbonyl, CO 2 H or cyano;
  • R 10 is C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 cycloalkyl optionally substituted with 1-4 C r C 3 alkyl or C 3 -C 6 halocycloalkyl;
  • R 1 ! is cyano, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylcarbonyl, S(O) n R 13 or
  • each R 12 is independently H or C r C 6 alkyl
  • R 13 is C r C 6 alkyl or C r C 6 alkoxy
  • R 12 and R 13 can be taken together as -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 - or -CH 2 CH 2 OCH 2 CH 2 -;
  • R 14 is H, C,-C 6 alkyl, C C 6 haloalkyl, C 2 -C 6 alkoxyalkyl, formyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C(O)NR 12 R 13 , C,-C 6 alkylsulfonyl or C j -C ⁇ haloalkylsulfonyl; or R 14 is phenyl, benzyl, benzoyl, -CH 2 C(O)phenyl or phenylsulfonyl, each optionally substituted on the phenyl ring with C1-C3 alkyl, halogen, cyano or nitro; R 15 is NR 12 R 13 , C r C 6 alkoxy, C,-C 6 haloalkoxy, C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C£ alkenyl, C 3
  • C j -C 3 haloalkyl C ⁇ -C 3 alkoxy, C C 3 haloalkoxy, 1-2 halogen, cyano or nitro
  • R 16 is C r C 3 alkoxy, C 2 -C alkoxycarbonyl, C r C 3 alkylthio, C j -C 3 alkylsulfinyl or C r C 3 alkylsulfonyl; or R 16 is phenyl optionally substituted with C r C 3 alkyl, Cj-C 3 haloalkyl, C1-C3 alkoxy, C r C 3 haloalkoxy, 1-2 halogen, cyano or nitro;
  • m is O, 1, 2 or 3;
  • n is 0, 1 or 2;
  • p is O, 1, 2, 3 or 4;
  • r is 1, 2 or 3; and
  • t is 0 or 1 ; provided that when W is CH and A is in the meta position with respect to
  • alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, H-propyl, -propyl, or the different butyl, pentyl or hexyl isomers.
  • 1-2 alkyl indicates that one or two of the available positions for that substituent may be alkyl.
  • Alkenyl includes straight-chain or branched alkenes such as 1-propenyl, 2-pro ⁇ enyl, 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 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. "Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. "Alkoxyalkyl” denotes alkoxy substitution on alkyl.
  • alkoxyalkyl examples include CH 3 OCH 2 , CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 , CH 3 CH 2 CH 2 OCH 2 and CH 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.
  • alkylsulfinyl examples include CH 3 S(O), CH 3 CH 2 S(O), CH 3 CH 2 CH 2 S(O), (CH 3 ) 2 CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers.
  • alkylsulfonyl examples include CH 3 S(O) 2 , CH 3 CH 2 S(O) 2 , CH 3 CH 2 CH 2 S(O) 2 , (CH 3 ) 2 CHS(O) 2 and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers.
  • alkylamino “dialkylamino”, and the like, are defined analogously to the above examples.
  • Cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • halogen either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl", said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” include F 3 C, C1CH 2 , CF 3 CH 2 and CF 3 CC1 2 .
  • haloalkoxy examples include CF 3 O, CCl 3 CH 2 O, HCF 2 CH 2 CH 2 O and CF 3 CH 2 O.
  • haloalkylthio examples include CC1 3 S, CF 3 S, CC1 3 CH 2 S and C1CH 2 CH 2 CH 2 S.
  • haloalkylsulfonyl examples include CF 3 S(O) 2 , CCl 3 S(O) 2 , CF 3 CH 2 S(O) 2 and CF 3 CF 2 S(O) 2 .
  • 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 6.
  • C ] -C 3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl
  • C 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 .
  • alkylcarbonyl examples include C(O)CH 3 , C(O)CH 2 CH 2 CH 3 and C(O)CH(CH 3 ) 2 .
  • Stereoisomers of this invention can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s).
  • the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
  • the present invention comprises compounds selected from Formula I, /V-oxides and agriculturally suitable salts thereof.
  • the compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.
  • Some compounds of this invention can exist as one or more tautomers.
  • compounds of Formula la (Formula I where Q is Q-1, R 3 is OR 14 , and R 14 is H) can also exist as the tautomers of Formulae lb and Ic as shown below.
  • said tautomers often exist in equilibrium with each other. As these tautomers interconvert under environmental and physiological conditions, they provide the same useful biological effects.
  • the present invention includes mixtures of such tautomers as well as the individual tautomers of compounds of Formula I.
  • the salts of the compounds of the invention 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.
  • 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.
  • the salts of the compounds of the invention also include those formed with organic bases (e.g., pyridine, ammonia, or triethylamine) or inorganic bases (e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium) when the compound contains an acidic group such as a carboxylic acid or enol.
  • organic bases e.g., pyridine, ammonia, or triethylamine
  • inorganic bases e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium
  • Preferred salts include the lithium, sodium, potassium, triethylammonium, and quaternary ammonium salts of the compounds of the invention.
  • Preferred compounds for reasons of better activity and/or ease of synthesis are: Preferred 1.
  • A is selected from the group lH-pyrrolyl; furanyl; thienyl; lH-pyrazolyl; lH-imidazolyl; isoxazolyl; oxazolyl; isothiazolyl; thiazolyl; lH-l,2,3-triazolyl; 2H-l,2,3-triazolyl; lH-l,2,4-triazolyl; 4H-l,2,4-triazolyl;
  • each R 1 is independently C ] -C 3 alkyl, C j -C 3 alkoxy, halogen or nitro;
  • R3 is OR 14 ;
  • R 14 is ⁇ or C j -C alkylsulfonyl; or R 14 is benzoyl or phenylsulfonyl, each optionally substituted with C C 3 alkyl, halogen, cyano or nitro.
  • Preferred 4 Compounds of Preferred 3 wherein:
  • A is pyridinyl, pyridazinyl, pyrimidinyl or lH-pyrazolyl;
  • R 2 is -(Y) t -S(O) n R 15 , CF 3 , OCF 3 , OCF 2 ⁇ or cyano;
  • R15 is C r C 6 alkyl; t is 0; and n is 2.
  • Q is Q-2;
  • Preferred 6 Compounds of Preferred 5 wherein: each R 1 is independently Cj-C 3 alkyl, C r C 3 alkoxy, halogen or nitro; R5 is OR 14 ;
  • R 14 is H or C
  • R 6 is H, C r C 6 alkyl, or C 3 -C 6 alkenyl; and R7 is H;
  • A is pyridinyl, pyridazinyl, pyrimidinyl or lH-pyrazolyl;
  • R 2 is -(Y) t -S(O) n R 15 , CF 3 , OCF 3 , OCF 2 ⁇ or cyano;
  • Rl5 is C r C 6 alkyl; t is 0; and n is 2.
  • Preferred 8 Compounds of Preferred 1 wherein: Q is Q-3.
  • each R 1 is independently C j -C 3 alkyl, C j -C 3 alkoxy, halogen or nitro;
  • R 8 is H, C.-C 3 alkyl, or cyclopropyl; and
  • R 9 is H or C 2 -C 3 alkoxycarbonyl.
  • A is pyridinyl, pyridazinyl, pyrimidinyl or lH-pyrazolyl;
  • R 2 is -(Y),-S(O) n R 15 , CF 3 , OCF 3 , OCF 2 ⁇ or cyano;
  • R15 is C,-C 6 alkyl; t is 0; and n is 2.
  • each R 1 is independently C r C 3 alkyl, C C 3 alkoxy, halogen or nitro;
  • R 10 is CyCf, cycloalkyl or C 3 -C6 halocycloalkyl, each optionally substituted with 1-4 C j -C 3 alkyl; and
  • R 1 * is cyano or C 2 -Cg alkoxycarbonyl.
  • Preferred 13 Compounds of Preferred 12 wherein:
  • A is pyridinyl, pyridazinyl, pyrimidinyl or lH-pyrazolyl;
  • R 2 is -(Y) r S(O) n R 15 , CF 3 , OCF 3 , OCF 2 ⁇ or cyano;
  • R'5 is C r C 6 alkyl; t is 0; and n is 2.
  • Most preferred are compounds of Formula la above, and sodium, potassium, and quaternary ammonium salts thereof, selected from the group: a) 3-hydroxy-2-[[6-(trifluoromethyl)[2,4'-bipyridin]-3-yl]carbonyl]-2- cyclohexen-1-one; b) 2-[2-chloro-4-(4-pyridinyl)benzoyl]-3-hydroxy-2-cyclohexen- 1 -one; and c) 2-[2,5-dimethyl-3-( 1 -methyl- lH-pyrazol-3-yl)-4-(methylsulfonyl)benzoyl]- 3-hydroxy-2-cyclohexen-l-one.
  • This invention also relates to herbicidal compositions comprising herbicidally effective amounts of the compounds of the invention and at least one of a surfactant, a solid diluent or a liquid diluent.
  • This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the compounds of the invention (e.g., as a composition described herein).
  • the preferred methods of use are those involving the above preferred compounds.
  • the compounds of Formula I can be prepared by one or more of the following methods and variations as described in Schemes 1-22.
  • the definitions of W, Y, A, R ! -R 16 , m, n, p, r, and t in the compounds of Formulae 1-22 below are as defined above in the Summary of the Invention.
  • Compounds of Formulae Ia-Ig are various subsets of the compounds of Formula I, and all substituents for Formulae Ia-Ig are as defined above for Formula I.
  • Id Scheme 1 illustrates the preparation of compounds of Formula Id (R 3 is OR 17 and R 17 is the same as R 14 as described in the Summary of the Invention excluding H) whereby a compound of Formula Id (R 3 is OH) is reacted with a reagent of Formula 1 in the presence of a base wherein X 1 is chlorine, bromine, fluorine, trifluorosulfonyloxy (OTf) or acetyloxy (OAc) and R 17 is as previously defined.
  • X 1 is chlorine, bromine, fluorine, trifluorosulfonyloxy (OTf) or acetyloxy (OAc) and R 17 is as previously defined.
  • the coupling is carried out by methods known in the art (or by slight modification of these methods): for example, see K. Nakamura, et al., WO 95/04054.
  • R' 7 is the same as R' as described in the Summary of the Invention excluding H;
  • X 1 is chlorine, bromine, fluorine, trifluorosulfonyloxy (OTf) or acetyloxy (OAc)
  • Scheme 2 illustrates the preparation of compounds of Formula Id (R 3 is SO n R 18 ; n is 1 or 2; and R 18 is Cj-Cg alkyl or C]-C 6 haloalkyl) whereby a compound of Formula Id (R 3 is SR 18 ) is reacted with an oxidizing reagent such as peroxyacetic acid, m-chloroperoxybenzoic acid, potassium peroxymonosulfate (e.g., Oxone®, available from Aldrich Chemical Company), or hydrogen peroxide (the reaction may be buffered with a base such as sodium acetate or sodium carbonate).
  • an oxidizing reagent such as peroxyacetic acid, m-chloroperoxybenzoic acid, potassium peroxymonosulfate (e.g., Oxone®, available from Aldrich Chemical Company), or hydrogen peroxide (the reaction may be buffered with a base such as sodium acetate or sodium carbonate).
  • the oxidation is carried
  • R ⁇ is C1-C6 alkyl or C ⁇ -C(, haloalkyl
  • Nu is SR 18 or OR 19 ; M is Na, K or Li; and R 19 is Cj-C6 alkyl, Cj-C ⁇ haloalkyl or C -C6 alkoxyalkyl
  • Compounds of Formula Id (R 3 is halogen) can be prepared by reacting a compound of Formula Id (R 3 is OH) with a halogenating reagent such as oxalyl bromide or oxalyl chloride (Scheme 4). This conversion is carried out by methods known in the art (or by slight modification of these methods): for example see S. Muller, et al., WO 94/13619; S. Muller, et al., DE 4,241,999.
  • a halogenating reagent such as oxalyl bromide or oxalyl chloride
  • Halogenating reagent e.g., oxalyl bromide, oxalyl chloride
  • Scheme 5 illustrates the preparation of compounds of Formula Id (R 3 is OH), whereby an enol ester of Formula 3 is reacted with a base such as triethylamine in the presence of a catalytic amount of cyanide source (e.g., acetone cyanohydrin or potassium cyanide).
  • cyanide source e.g., acetone cyanohydrin or potassium cyanide.
  • Enol esters of Formula 3 can be prepared by reacting a dione of Formula 4 with an acid chloride of Formula 5 in the presence of a slight mole excess of a base such as triethylamine in an inert organic solvent such as acetonitrile, methylene chloride or toluene at temperatures between 0 °C and 110 °C (Scheme 6).
  • a base such as triethylamine
  • an inert organic solvent such as acetonitrile, methylene chloride or toluene
  • the acid chlorides of Formula 5 can be prepared by one skilled in the art by reacting an acid of Formula 6 with oxalyl chloride (or thionyl chloride) and a catalytic amount of dimethylformamide (Scheme 7). This chlorination is well known in the art: for example, see W. J. Michaely, EP 369,803.
  • Enol esters of Formula 3a can also be prepared by directly reacting the acid of Formula 6a with N-methyl-2-chloropyridinium iodide, followed by treatment of the formed intermediate with the dione of Formula 4 in the presence of a base such as triethylamine (Scheme 8).
  • This coupling is carried out be methods known in the art (or by slight modification of these methods): for example, see E. Haslam Tetrahedron (1980), 36, 2409-2433. 530
  • Scheme 9 illustrates the preparation of acids of Formula 6 (R 1 is S(O) n R 15 and n is 1 or 2) whereby an acid of Formula 6 (R 1 is SR 15 ) is reacted with an oxidizing reagent such as peroxyacetic acid, w-chloroperoxybenzoic acid, Oxone®, or hydrogen peroxide (the reaction may be buffered with a base such as sodium acetate or sodium carbonate).
  • an oxidizing reagent such as peroxyacetic acid, w-chloroperoxybenzoic acid, Oxone®, or hydrogen peroxide
  • a base such as sodium acetate or sodium carbonate
  • R 1 is S(0) n R 15 and n is 0 wherein R 1 is S(0) n R 15 and n is 1 or 2
  • Scheme 10 illustrates the preparation of acids of Formula 6 (n is 0 if R 1 is S(O) n R 15 ) whereby a phenyl bromide of Formula 7 (n is 0 if R 1 is S(O) n R 15 ) is treated with n-butyllithium (or magnesium) and the lithium salt (or the Grignard reagent) generated in situ is then reacted with carbon dioxide followed by acidification with an acid such as hydrochloric acid.
  • This conversion is carried out by methods known in the art (or by slight modification of these methods): for example, see M. A.
  • acids of Formula 6 can also be prepared, as shown in Scheme 1 1 , whereby an ester of Formula 8 is saponified (for example, potassium hydroxide in methanol, then acidification with an acid such as hydrochloric acid), or, alternatively, hydrolyzed in acid (for example, 5/V hydrochloric acid in acetic acid) by methods known in the art (or slight modification of these methods); see for example, M. A. Ogliaruso, et al., Synthesis of Carboxylic Acids, Esters and Their Derivatives, John Wiley & Sons,
  • R " is CH 3 or CH 2 CH 3 530
  • Esters of Formula 8 can be prepared using methods known in the art (or by slight modification of these methods): for example, see A. R. Katritzky, et al., Comprehensive Heterocyclic Chemistry, volumes 2-6, Pergamon Press.
  • Esters of Formula 8a or 8b can also be prepared as shown in Scheme 12, whereby an ester of Formula 9a or 9b is contacted with an appropriate nucleophilic heterocycle Nu 1 and a suitable base in an inert solvent.
  • This reaction can be carried out by a variety of well-known methods, preferably with potassium carbonate or potassium tert-butoxide as the base with N,N-dimethylfoimamide as the solvent and at a reaction temperature range of from approximately 0 to 100 °C.
  • X 3 is Cl, F or CF 3 S0 0, wherein A l is 1 /-imidazole, l/Z-pyrazole, l -l,2,4-t ⁇ azole or 4/7-1,2,4-t ⁇ azole
  • Nu ' is an imidazole, pyrazole or t ⁇ azole
  • Esters of Formula 9a and 9b are commercially available or can be prepared using methods known in the art (or by slight modification of these methods).
  • Scheme 13 illustrates the preparation of acids of Formula 6a whereby an aryl bromide of Formula 9c is treated with an aryl tin reagent in the presence of a palladium catalyst. This conversion is carried out by methods known in the art (or by slight modification of these methods): for example, see M. Fujta, et al., Tetrahedron Letters, (1995), 29, 5247-5250; Y. Yamamoto, et al., Heterocycles, (1996), 42, 189-194. Saponification of the ester with a base such as sodium hydroxide provides the acids of Formula 6a.
  • Bromides of Formula 9c are either commercially available or can easily be prepared by methods known in the art (or by slight modification of these methods): for example, see T. Bryson, et al., J. Org. Chem., (1976), 41, 2066; Andrea, T. A. and
  • Aryl and heteroaryl organotin compounds can be prepared by methods known in the art (or by slight modification of these methods): for example, see D. Peters, et al., J. Heterocyclic Chem., (1990), 27, 2165.
  • Bromides of Formula 7 (n is 0 if Rl is S(O) n R 15 ) can be prepared by one skilled in the art by using methods known in the art (or by slight modification of these methods): for example, see A. R. Katritzky, et al., Comprehensive Heterocyclic Chemistry, Volume 2-6, Pergamon Press; B. M. Lynch, et al., Tel. Lett. (1964), p. 617; M. A. ahn, et al., Rev. Latinoam. Quim. (1972), 3, p. 1 19; M. Kosugi, et al., Bull. Chem. Soc. Jpn. (1986), 59 (2), p. 677.
  • bromides of Formula 7 (n is 0 if R 1 is S(O) n Rl 5 ) can also be prepared by bromination of the corresponding substituted benzenes of Formula 8 (n is 0 if Rl is S(O) n R l5 ) with the bromine or other equivalent reagent in an inert organic solvent as shown in Scheme 14.
  • This bromination is carried out by general methods known in the art; see, for example, E. Campaigne, et al., J. Heterocycl. Chem. (1969), 6, p. 517; H. Gilman, J. Am. Chem. Soc. (1955), 77, p. 6059;
  • the compounds of Formula 8 (n is 0 if R 1 is S(O) n R 15 ) can be prepared by one skilled in the art by using methods known in the art (or by slight modification of these methods): for example, see A. R. Katritzky, et. al., Comprehensive Heterocyclic Chemistry, Volume 2-6, Pergamon Press; B. M. Lynch, et al., Tet. Lett. (1964), p. 617; 530
  • Scheme 15 illustrates the preparation of compounds of Formula le (R 14 is R 14a and R ⁇ 4a is the same as R l as described in the Summary of the Invention excluding H) whereby a compound of Formula le ( R' 4 is H) is reacted with a reagent of Formula 9 in the presence of a base wherein X 2 is chlorine, bromine, fluorine, OTf or OAc and R , 4a is as previously defined.
  • This coupling is carried out by methods known in the art (or by slight modification of these methods): for example, see K. Nakamura, et al., WO 95/04054.
  • Scheme 16 illustrates the preparation of compounds of Formula le (R 14 is H). whereby an ester of Formula 10 is reacted with a base such as triethylamine in the presence of a catalytic amount of cyanide source (e.g., acetone cyanohydrin or potassium cyanide).
  • cyanide source e.g., acetone cyanohydrin or potassium cyanide.
  • Esters of Formula 10 can be prepared by reacting a hydroxypyrazole of Formula 11 with an acid chloride of Formula 5 in the presence of a slight mole excess of a base such as triethylamine in an inert organic solvent such as acetonitrile, methylene chloride or toluene at temperatures between 0 °C and 110 °C (Scheme 17).
  • a base such as triethylamine
  • an inert organic solvent such as acetonitrile, methylene chloride or toluene
  • Scheme 18 illustrates the preparation of compounds of Formula If whereby a compound of Formula 12 is reacted with a salt of hydroxylamine such as hydroxylamine hydrochloride in the presence of a base or acid acceptor such as triethylamine or sodium acetate.
  • a base or acid acceptor such as triethylamine or sodium acetate.
  • the substituents of the immediate products may be further modified if appropriate. This cyclization is carried out by methods known in the art (or by slight modification of these methods): for example, see P. A. Cain, et al., EP 560,483; C. J. Pearson, et al., EP 636,622. 530
  • L is a leaving group such as C ] -C 4 alkoxy (e.g. OC 2 H5) or V-dialkylamino (e.g. dimethyl amino)
  • R 9 a is R 9 or CONH 2
  • Scheme 19 illustrates the preparation of compounds of Formula 12 whereby a compound of Formula 13 is reacted with a reagent of Formula 14 or Formula 15. This conversion is carried out by methods known in the art (or by slight modification of these methods): for example, see P. A. Cain, et al., EP 560,483; C. J. Pearson, et al., EP 636,622.
  • Scheme 20 illustrates the preparation of compounds of Formula 13 whereby a ester of Formula 16 is decarboxylated in the presence of a catalyst, such as -toluenesulfonic acid, in an inert solvent such as toluene.
  • a catalyst such as -toluenesulfonic acid
  • an inert solvent such as toluene.
  • Esters of Formula 16 can be prepared by reacting the metal salt of a compound of
  • Scheme 22 illustrates the preparation of compounds of Formula Ig whereby a compound of Formula 5 is reacted with a compound of Formula 18 in the presence of a base such as triethylamine, potassium carbonate, sodium hydride or Mg(OEt) 2 in an inert organic solvent such as diethyl ether, tetrahydrofuran, NN-dimethylformamide, dichloromethane or acetonitrile.
  • a base such as triethylamine, potassium carbonate, sodium hydride or Mg(OEt) 2
  • an inert organic solvent such as diethyl ether, tetrahydrofuran, NN-dimethylformamide, dichloromethane or acetonitrile.
  • Step B Preparation of 2,3-dihvdro-5,8-dimethyl-4H-l -benzopyran-4-one
  • Step C Preparation of 6-bromo-2,3-dihvdro-5,8-dimethyl-4H- 1 -benzothiopyran-
  • Step D Preparation of 6-bromo-5,8-dimethyl-4H- 1 -benzothiopyran-4-one
  • Step E Preparation of 3-[3-bromo-2,5-dimethyl-6-(methylthio)phenvn- 1-methyl- lH-pyrazole 13.25 g (0.049 mol) of the title compound of step D and 2.88 mL (0.054 mol) of methylhydrazine (purchased from Aldrich Chemical Company) was added to 150 mL of absolute ethanol. After stirring at reflux under nitrogen for 5 hr the mixture was allowed to warm to room temperature and stir for 2.5 days.
  • step E 5.9 g (0.019 mol) of the title compound of step E was added to 100 mL of tetrahydrofuran and cooled to -70 °C. 9.1 mL (0.023 mol) of 2.5M ⁇ -butyllithium (purchased from Aldrich Chemical Company) was added dropwise keeping the temperature below -65 C. Solid carbon dioxide was added in one portion and the mixture warmed to room temperature. 200 mL of hexane was added and the mixture was filtered. The solid collected was added to water and acidified to about p ⁇ 1 with concentrated hydrochloric acid.
  • Step G Preparation of 2,5-dimethyl-3-(l -methyl- lH-pyrazol-3-yl)-4-
  • Step H Preparation of 3-oxo-l-cylcohexen-l-yl 2,5-dimethyl-3-(l-methyl-lH- pyrazol-3-yl)-4-(methylsulfonyl)benzoate 1.39 g (0.0045 mol) of the title compound of step G, 1.18 mL (0.0135 mol) of oxalyl chloride (purchased from Janssen), and 2 drops of N,N-dimethylformamide were added to 50 mL of methylene chloride. The mixture was refluxed under nitrogen for 2.5 hr and was then evaporated to dryness. 50 mL of methylene chloride was added to the residue and the solution was again evaporated to dryness.
  • Step B Preparation of 3-oxo- 1 -cyclohexen- 1 -yl 2-r3-(trifluoromethyl)- 1 H- pyrazol- 1 -yllbenzoate
  • oxalyl chloride oxalyl chloride
  • the suspension was refluxed for about 3 hours and then concentrated under reduced pressure.
  • the residue was azeotroped with dichloromethane (two times with 20 mL at 60 °C) to yield an oil which solidified upon cooling and melted at 64-68 °C.
  • Step C Preparation of 3-hvdroxy-2-r2-f3-(trifluoromethyl)-lH-pyrazol- l- yllbenzovn-2-cvclohexen-l-one To 20 mL of acetonitrile was added sequentially 1.8 g (0.005 mol) of the title compound of Step B, 1.0 g (0.01 mol) of triethylamine, and 8 drops of acetone cyanohydrin.
  • Step D Preparation of 3-hvdroxy-2-f[6-(trifluoromethyl)f2,4'-bipyridin1-3- yllcarbonvn-2-cvclohexen- 1 -one To a solution of 1.22 g (3.5 mmol) of the title compound of Step C in 25 mL of acetonitrile was added 1.16 mL (8.36 mmol) of triethylamine, followed by 2 drops of acetonecyanohydrin.
  • A-53 (3-methyl- l,2,4-oxad ⁇ azol-5-yl)-
  • A-79 (4-methyl-2-py ⁇ m ⁇ d ⁇ nyl)-
  • A-60 (3-methyl l ,2,4-th ⁇ ad ⁇ azol-5-yl)-
  • A-86 (6-methyl-2-pyrazmyl)-
  • A-61 (5-methyl-l ,2,4-th ⁇ ad ⁇ azol-3-yl)-
  • A-87 (2-pyraz ⁇ nyl)-
  • A-62 (4-methyl- l ,2,5-th ⁇ ad ⁇ azol-3-yl)-
  • A-88 (4,6-d ⁇ methyl- I ,3,5-t ⁇ az ⁇ n-2-yl)-
  • A-63 (5-methyl- l ,3,4-th ⁇ ad ⁇ azol-2-yl)-
  • A-89 (4,6-d ⁇ chloro- l,3,5-t ⁇ az ⁇ n-2-yl)-
  • A-64 (l-methyl-l/7-tetrazol-5-yl)-
  • A-90 (l ,3,5-t ⁇ az ⁇ n-2-yl)-
  • A-65 (l//-tetrazol-5-yl)-
  • A-91 (4-methyl- 1,3,5-t ⁇ az ⁇ n- 2-yl)-
  • A-66 (5-methyl-l /-tetrazol-l-yI)-
  • A-92 (3-methyl- l ,2,4-t ⁇ az ⁇ n-5-yl)-
  • A-67 (2-methyl-2/ -tetrazol-5-yl)-
  • A-93 (3-methyl- l,2,4-t ⁇ az ⁇ n-6-yl)-
  • A-68 (2-ethyl-2/ -tetrazol-5-yl)-
  • A-69 (5-methyl-2 /-tetrazol-2-yl)-
  • A-70 (2 -tetrazol-2-yl)-
  • A-71 (2-py ⁇ d ⁇ nyl)-
  • A-72 (6-methyl-2-py ⁇ d ⁇ nyl)-
  • A-73 (4-py ⁇ d ⁇ nyl)-
  • A-74 (3-py ⁇ d ⁇ nyl)-
  • A-75 (6-methyl-3-py ⁇ daz ⁇ nyl)-
  • A-76 (5-methyl -3-py ⁇ daz ⁇ nyl)- 97/46530
  • R 15 is CT and R 6 is CH 2 CH 3
  • A-42 S0 2 N(CH 3 ) 2 CH 3 CH 3
  • A-44 S0 2 N(CH 3 ) 2 CH 3 CH 3
  • A-42 S0 2 OCH 2 CF 3 CH 3 CH 3
  • A-44 S0 2 OCH 2 CF 3 CH 3 CH 3
  • R la is CH, R lb is CN, and W is N
  • Rla is Cl.
  • R lb is Cl. and W is CH
  • Rla is CH .
  • R lb is SO 2 CH ? . and W is N
  • R ⁇ a is CH , R b is H, and W is N
  • Rl a isCl.R lb isCl.andWisCH
  • Rla is isCH
  • Rla is Cl.
  • R l b is Cl. and W is N
  • Rla is Cl.
  • R lb is Cl. and W is CH
  • Compounds of this invention will generally be used as a formulation or composition with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant.
  • the formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.
  • Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels.
  • Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible ("wettable") or water-soluble.
  • Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated”). Encapsulation can control or delay release of the active ingredient.
  • Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation.
  • the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.
  • Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.
  • Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers.
  • Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
  • Liquid diluents include, for example, water, ⁇ /,/V-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-mefhyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.
  • Solutions can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S.
  • Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4, 144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566.
  • Example A High Strength Concentrate Compound 1 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0%.
  • Compound 15 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%.
  • Granule Compound 25 10.0% attapulgite granules (low volatile matter
  • Example D Extruded Pellet Compound 26 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%.
  • Test results indicate that the compounds of the present invention are highly active preemergent and postemergent herbicides or plant growth regulants. Many of them have utility for broad-spectrum pre- and/or postemergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-in theaters, air fields, river banks, irrigation and other waterways, around billboards and highway and railroad structures.
  • Some of the compounds are useful for the control of selected grass and broadleaf weeds with tolerance to important agronomic crops which include but are not limited to alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass).
  • important agronomic crops which include but are not limited to alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato,
  • a herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of compounds of this invention is 0.001 to 20 kg/ha with a preferred range of 0.004 to 1.0 kg/ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.
  • Compounds of this invention can be used alone or in combination with other commercial herbicides, insecticides or fungicides. Compounds of this invention can also be used in combination with commercial herbicide safeners such as benoxacor, dichlormid and furilazole to increase safety to certain crops.
  • commercial herbicide safeners such as benoxacor, dichlormid and furilazole to increase safety to certain crops.
  • a mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, ametryn, amidosulfuron, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, bifenox, bispyribac and its sodium salt, bromacil, bromoxynil, bromoxynil octanoate, butachlor, butralin, butroxydim (ICIA0500), butylate, caloxydim (BAS 620H), carfentrazone-ethyl,
  • combinations with other herbicides having a similar spectrum of control but a different mode of action will be particularly advantageous for preventing the development of resistant weeds.
  • Preferred for better control of undesired vegetation (e.g., lower use rate, broader spectrum of weeds controlled, or enhanced crop safety) or for preventing the development of resistant weeds are mixtures of a compound of this invention with a herbicide selected from the group nicosulfuron, rimsulfuron, nicosulfuron in combination with rimsulfuron, imazethapyr, sethoxydim, glyphosate, and glufosinate.
  • the following Tests demonstrate the control efficacy of the compounds of this invention against specific weeds.
  • the weed control afforded by the compounds is not limited, however, to these species. See Index Tables A-D for compound descriptions. The abbreviation “dec.” indicates that the compound appeared to decompose on melting. The abbreviation “Ex.” stands for “Example” and is followed by a number indicating in which example the compound is prepared. INDEX TABLE A
  • Plants ranged in height from two to eighteen cm (one to four leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table A, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result.
  • the compounds evaluated in this test were formulated in a non-phytotoxic solvent mixture which includes a surfactant and applied to the soil surface before plant seedlings emerged (preemergence application), to water that covered the soil surface (flood application), and to plants that were in the one-to-four leaf stage (postemergence application).
  • preemergence application to water that covered the soil surface
  • postemergence application to plants that were in the one-to-four leaf stage
  • a sandy loam soil was used for the preemergence and postemergence tests, while a silt loam soil was used in the flood test. Water depth was approximately 2.5 cm for the flood test and was maintained at this level for the duration of the test.
  • Plant species in the preemergence and postemergence tests consisted of barnyardgrass (Echinochloa crus-galli), barley (Hordeum vulgare), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), cocklebur (Xanthium strumarium), corn (Zea mays v.
  • Plant species in the flood test consisted of rice (Oryza sativa), umbrella sedge (Cyperus difformis), duck salad (Heteranthera limosa), barnyardgrass2 (Echinochloa crus-galli) and Late watergrass (Echinochloa oryzicola grown to the 2 leaf stage for testing.
  • Plastic pots were partially filled with silt loam soil. The soil was then saturated with water.
  • Indica Rice Oryza saliva seed or seedlings at the 2.0 to 3.5 leaf stage; seeds, tubers or plant parts selected from arrowhead (Sagittaria rigida), barnyardgrass (Echinochloa crus- galli), ducksalad (Heteranthera limosa), early watergrass (Echinochloa oryzoides), junglerice (Echinochloa colonum), late watergrass (Echinochloa oryzicola), redstem (Ammonia species), rice flatsedge (Cyperus iria), smallflower flatsedge (Cyperus difformis) and tighthead sprangletop (Leptochloafasicularis), were planted into this soil.
  • Plantings and waterings of these crops and weed species were adjusted to produce plants of appropriate size for the test. At the two leaf stage, water levels were raised to 3 cm above the soil surface and maintained at this level throughout the test. Chemical treatments were formulated in a non-phytotoxic solvent mixture which includes a surfactant and applied directly to the paddy water, by pipette, or to the plant foliage, by an air-pressure assisted, calibrated belt-conveyer spray system.
  • alexandergrass (Brachiaria plantaginea), bermudagrass (Cynodon dactylon), broadleaf signalgrass (Brachiaria platyphylla), common purslane (Portulaca oleracea), common ragweed (Ambrosia elatior), cotton (Gossypium hirsutum), dallisgrass (Paspalum dilatatum), goosegrass (Eleusine indica), guineagrass (Panicum maximum), itchgrass (Rottboellia exaltat ⁇ ), Johnson grass (Sorghum halepense), large crabgrass (Digitaria sanguinalis), peanuts (Arachis hypogaea), pitted morningglory (Ipomoea lacunosa), purple nutsedge (Cyperus rotundus), sandbur (Cenchrus echinatus), sourgrass (Trichachne insularis), and Surinam grass (Brachiaria plantaginea), ber
  • Test chemicals were formulated in a non-phytotoxic solvent mixture which included a surfactant and applied preemergence and postemergence to the plants. Untreated control plants and treated plants were placed in the greenhouse and visually evaluated for injury 13 to 21 days after herbicide application. Plant response ratings, summarized in Table D, are based on a 0 to 100 scale where 0 is no injury and 100 is complete control. A dash (-) response means no test result.
  • soybean2 Glycine max v. Asgrow 3304
  • sunflower Helianthus annuus
  • velvetleaf Abutilon theophrasti
  • wild proso Pancium miliaceum
  • woolly cupgrass Eriochloa villosa
  • yellow foxtail Setaria lutescens
  • purple nutsedge Cyperus rotundus tubers
  • Crop and weed species include arrowleaf sida (Sida rhombifoli ⁇ ), barnyardgrass (Echinochloa crus-galli), cocklebur (Xanthium strumarium), common lambsquarters (Chenopodium album), corn (Zea mays), cotton (Gossypium hirsutum), eastern black nightshade (Solanum ptycanthum), fall panicum (Panicum dichotomiflorum), field bindweed (Convolvulus arvensis), Florida beggarweed (Desmodium purpureum), giant foxtail (Setaria faberii), hairy beggarticks (Bidens pilosa), ivyleaf morningglory (Ipomoea hederacea), johnsongrass (Sorghum halepense), ladys
  • Treated plants and untreated controls were maintained in a greenhouse for approximately 14 to 21 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table F, were based upon a 0 to 100 scale where 0 was no effect and 100 was complete control. A dash response (-) means no test result.
  • Crop and weed species include bristly starbur (Acanthospermun hispidum) alexandergrass (Brachiaria plantaginea), american black nightshade (Solanum americanum), apple-of-Peru (Nicandra physaloides), arrowleaf sida (Sida rhombifolia), Brazilian sicklepod (Cassia tora Brazilian), Surinam grass (Brachiaria decumbens), capim- colchao (Digitaria horizontalis), Crist, soybean (Glycine max v.
  • Cristalina florida beggarweed (Desmodium purpureum), hairy beggarticks (Bidens pilosa), slender amaranth (Amaranthus viridis), southern sandbur (Cenchrus echinatus), tall morningglory (Ipomoea purpurea), tropical spiderwort (Commelina benghalensis), W20 Soybean (Glycine max v. W20), W4-4 Soybean (Glycine max v. W4-4), corn (Zea mays v. Pioneer 3394) and wild pointsettia (Eupohorbia heterophylla).
  • Treated plants and untreated controls were maintained in a greenhouse for approximately 13 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table G, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control.
  • Braz Sicklepod 60 Braz Sicklepod 35 Braz Sicklepod 10
  • Capim-Colch 100 Capim-Colch 65
  • Capim-Colch 60 Corn 0 Corn 0 Corn 0
  • Morningglory 70 Morningglory 65 Morningglory 60
  • Crop and weed species include annual bluegrass (Poa annu ⁇ ), blackgrass (Alopecurus myosuroides), black nightshade (Solanum nigra), chickweed
  • Treated plants and untreated controls were maintained in a greenhouse for approximately 21 to 28 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table H, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash response (-) means no test result.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Composés de formule (I) et leurs N-oxydes et sels appropriés pour l'agriculture, qui sont utiles pour lutter contre la végétation non désirée. Dans ladite formule, Q est Q-1, Q-2, Q-3 ou Q-4 et A, W, R?1, R3-R11¿ et m sont tels que définis dans le descriptif. La présente invention concerne également des compositions contenant les composés de formule (I) et un procédé de lutte contre la végétation non désirée qui consiste à mettre en contact ladite végétation ou son environnement avec une quantité efficace d'un composé de formule (I).
EP97928809A 1996-06-06 1997-06-02 Pyridinylcetones et pyrazolylphenylcetones herbicides Withdrawn EP0922032A1 (fr)

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US1935296P 1996-06-06 1996-06-06
US19352P 1996-06-06
US3363396P 1996-12-20 1996-12-20
US33633P 1996-12-20
PCT/US1997/009569 WO1997046530A1 (fr) 1996-06-06 1997-06-02 Pyridinylcetones et pyrazolylphenylcetones herbicides

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