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(12) United States Patent (10) Patent No.: US 8,530,667 B2 Jeanmart Et Al

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(12) United States Patent (10) Patent No.: US 8,530,667 B2 Jeanmart Et Al USOO853.0667B2 (12) United States Patent (10) Patent No.: US 8,530,667 B2 Jeanmart et al. (45) Date of Patent: Sep. 10, 2013 (54) HERBICIDES (52) U.S. Cl. USPC .......... 548/100: 548/204:546/287.7: 549/60; (75) Inventors: Stephane André Marie Jeanmart, 549/459; 549/78; 54.4/318 Bracknell (GB); John Benjamin Taylor, (58) Field of Classification Search Bracknell (GB); Melloney Tyte, None Bracknell (GB); Christopher John See application file for complete search history. Mathews, Bracknell (GB); Stephen Christopher Smith, Bracknell (GB) (56) References Cited (73) Assignee: Syenta Limited, Guildford, Surrey U.S. PATENT DOCUMENTS (GB) 2005, 0164883 A1 7/2005 Maetzke (*) Notice: Subject to any disclaimer, the term of this 58-385 A. 585 May patent is extended or adjusted under 35 2012/0094832 A1 4/2012 Tyte et al. U.S.C. 154(b) by 116 days. 2012/0142529 A1 6/2012 Tyte et al. (21) Appl. No.: 12/675,975 FOREIGN PATENT DOCUMENTS WO 96.03366 2, 1996 (22) PCT Filed:1-1. Sep. 1, 2008 WO O17477O9948869 10,9, 20011999 (86). PCT No.: PCT/EP2008/007 132 W. 3352 1358. S371 (c)(1), Primary Examiner — Nyeemah A Grazier (2), (4) Date: Jun. 15, 2010 (74) Attorney, Agent, or Firm — R. Kody Jones (87) PCT Pub. No.: WO2009/030450 (57) ABSTRACT PCT Pub. Date: Mar. 12, 2009 Compounds of formula (I) wherein the substituents are as (65) Prior Publication Data defined in claim 1, are suitable for use as herbicides. US 2010/O29814.0 A1 Nov. 25, 2010 (I) (30) Foreign Application Priority Data Sep. 3, 2007 (GB) ................................... 07170822 (51) Int. Cl. C07D 293/00 (2006.01) C07D 277/30 (2006.01) CO7D 409/00 (2006.01) C07D 307/00 (2006.01) CO7D 333/6 (2006.01) CO7D 405/00 (2006.01) C07D 239/02 (2006.01) 13 Claims, No Drawings US 8,530,667 B2 1. 2 HERBCDES alkoxy, tri(C-C)alkylsilyl (C-C)alkoxy, C-C alkoxycar bonyl(C-C)alkoxy, C-Cohaloalkoxy, aryl(C-C)alkoxy This application is a 371 of International Application No. (where the aryl group is optionally Substituted), C-C, PCT/EP2008/007 132 filed Sep. 1, 2008, which claims prior cycloalkyloxy (where the cycloalkyl group is optionally Sub ity to GB 0717082.2 filed Sep. 3, 2007, the contents of which stituted with C-C alkyl or halogen), C-Co alkenyloxy, are incorporated herein by reference. Cs-Co alkynyloxy, mercapto, C-Co alkylthio, C-Co The present invention relates to novel, herbicidally active haloalkylthio, aryl (C-C)alkylthio (where the aryl group is cyclopentanedione compounds, and derivatives thereof, to optionally substituted), C-C, cycloalkylthio (where the processes for their preparation, to compositions comprising cycloalkyl group is optionally substituted with C-C alkyl or 10 halogen), tri(C-C)alkylsilyl(C-C)alkylthio, arylthio those compounds, and to their use in controlling weeds, espe (where the aryl group is optionally Substituted), C-C alkyl cially in crops of useful plants, or in inhibiting undesired plant Sulfonyl, C-Chaloalkylsulfonyl, C-C alkylsulfinyl, C-C, growth. haloalkylsulfinyl, arylsulfonyl (where the aryl group may be Cyclopentanedione compounds having herbicidal action optionally substituted), tri(C-C)alkylsilyl, aryldi(C-C) are described, for example, in WO 01/74770 and WO 15 alkylsilyl (C-C)alkyldiarylsilyl, triarylsilyl, aryl(C-C) 96/03366. alkylthio(C-C)alkyl, aryloxy(C-C)alkyl, formyl, C-Co Novel cyclopentanedione compounds, and derivatives alkylcarbonyl, HOC, C-C alkoxycarbonyl, aminocarbo thereof, having herbicidal and growth-inhibiting properties nyl, C-C alkylaminocarbonyl, di(C-C alkyl)aminocarbo have now been found. nyl, N-(C-C alkyl)-N-(C-C alkoxy)aminocarbonyl, The present invention accordingly relates to compounds of C-C alkylcarbonyloxy, arylcarbonyloxy (where the aryl formula (I) group is optionally substituted), di(C-C)alkylaminocarbo nyloxy, C-Calkyliminooxy, C-Calkenyloxyimino, ary loxyimino, aryl (itself optionally substituted), heteroaryl (it (I) self optionally substituted), heterocyclyl (itself optionally 25 substituted with C-C alkyl or halogen), aryloxy (where the aryl group is optionally Substituted), heteroaryloxy, (where the heteroaryl group is optionally Substituted), heterocycly loxy (where the heterocyclyl group is optionally substituted with C-C alkyl or halogen), amino, C-C alkylamino, 30 di(C-C)alkylamino, C-C alkylcarbonylamino, N-(C- C.)alkylcarbonyl-N-(C-C)alkylamino, C-C alkenylcar bonyl, C-C alkynylcarbonyl, C-C alkenyloxycarbonyl, C-C alkynyloxycarbonyl, aryloxycarbonyl (where the aryl wherein group is optionally Substituted) and arylcarbonyl (where the R" and R are independently of each other hydrogen, 35 aryl group is optionally Substituted). C-C alkyl, C-Chaloalkyl, C-Calkoxy, C-C alkylthio. Alkenyl and alkynyl moieties can be in the form of straight halogen or C-Calkoxycarbonyl, or branched chains, and the alkenyl moieties, where appro R. R. R. R. R. and R7 are independently of each other priate, can be of either the (E)- or (Z)-configuration. hydrogen or a Substituent, or Examples are vinyl, allyl and propargyl. Alkenyl and alkynyl R" and R. RandR, or RandR together with the carbon 40 moieties can contain one or more double and/or triple bonds atoms to which they are attached form an optionally Substi in any combination. It is understood, that allenyl and alkyli tuted ring, optionally containing a heteroatom, or nylalkenyl are included in these terms. RandR together with the carbon atoms to which they are When present, the optional substituents on alkenyl or alky attached form a keto, imino or alkenyl unit, or nyl include those optional Substituents given above for an RandR together form a bond, 45 alkyl moiety. G is hydrogen or an alkali metal, alkaline earth metal, Sulfo Halogen is fluorine, chlorine, bromine or iodine. nium, ammonium or a latentiating group, Haloalkyl groups are alkyl groups which are substituted Het is an optionally substituted monocyclic or bicyclic het with one or more of the same or different halogen atoms and eroaromatic ring, and agronomically acceptable salts thereof. are, for example, CF, CFC, CFH, CC1H, FCH, CICH, In the substituent definitions of the compounds of the for 50 BrCH, CHCHF (CH),CF, CFCH or CHFCH. mula (I), each alkyl moiety either alone or as part of a larger In the context of the present specification the terms “aryl'. group (Such as alkoxy, alkoxycarbonyl, alkylcarbonyl, alky 'aromatic ring and 'aromatic ring system’ refer to ring laminocarbonyl, dialkylaminocarbonyl) is a straight or systems which may be mono-, bi- or tricyclic. Examples of branched chain and is, for example, methyl, ethyl, n-propyl. Such rings include phenyl, naphthalenyl, anthracenyl, indenyl n-butyl, n-pentyl, n-hexyl, iso-propyl. n-butyl, sec-butyl, iso 55 or phenanthrenyl. A preferred aryl group is phenyl. In addi butyl, tert-butyl or neopentyl. The alkyl groups are suitably tion, the terms "heteroaryl, "heteroaromatic ring or “het C to C alkyl groups, but are preferably C-C alkyl groups. eroaromatic ring system” refer to an aromatic ring system Ring forming alkylene, and alkenylene groups can option containing at least one heteroatom and consisting either of a ally be further substituted by one or more halogen, single ring or of two or more fused rings. Preferably, single C-C alkyl and/or C-Calkoxy groups. When present, the 60 rings will contain up to three and bicyclic systems up to four optional Substituents on an alkyl moiety (alone or as part of a heteroatoms which will preferably be chosen from nitrogen, larger group Such as alkoxy, alkoxycarbonyl, alkylcarbonyl, oxygen and Sulphur. Suitable examples of heteroaromatic alkylaminocarbonyl, dialkylaminocarbonyl) include one or rings are, for example, thienyl, furyl, pyrrolyl, isoxazolyl, more of halogen, nitro, cyano, C-C, cycloalkyl (itself oxazolyl, isothiazolyl, thiazolyl pyrazolyl, imidazolyl, tria optionally Substituted with C-C alkyl or halogen), Cs-C, 65 Zolyl, tetrazolyl pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, cycloalkenyl (itself optionally substituted with C-C alkyl or triazinyl, oxadiazolyl and thiadiazolyl, and, where appropri halogen), hydroxy, C-Co alkoxy, C-Co alkoxy(C-Co) ate, N-oxides and salts thereof. US 8,530,667 B2 3 4 The terms heterocycle and heterocyclyl preferably refer to C.)alkylamino (where the aryl group is substituted by C-C, a non-aromatic preferably monocyclic or bicyclic ring sys alkyl or halogen), aryl-N-(C-C)alkylamino (where the tems containing up to 7 atoms including one or more (pref aryl group is substituted by C-C alkyl or halogen), ary erably one or two) heteroatoms selected from O, S and N. lamino (where the aryl group is Substituted by C-C alkyl or Examples of Such rings include 1,3-dioxolane, oxetane, tet halogen), heteroaryl amino (where the heteroaryl group is rahydrofuran, morpholine, thiomorpholin and piperazine. Substituted by C-C alkyl or halogen), heterocyclylamino When present, the optional substituents on heterocyclyl (where the heterocyclyl group is substituted by C-C alkyl or include C-C alkyl and C-C haloalkyl as well as those halogen), aminocarbonylamino, C-C alkylaminocarbony optional Substituents given above for an alkyl moiety. lamino, di(C-C)alkylaminocarbonylamino, arylaminocar Cycloalkyl includes preferably cyclopropyl, cyclobutyl, 10 cyclopentyl and cyclohexyl. Cycloalkylalkyl is preferentially bonylamino where the aryl group is Substituted by C-C, cyclopropylmethyl. Cycloalkenyl includes cyclopentenyl alkyl or halogen), aryl-N-(C-C)alkylamino-carbony and cyclohexenyl. lamino where the aryl group is Substituted by C-C alkyl or When present, the optional substituents on cycloalkyl or halogen). C-Calkylaminocarbonyl-N-(C-C)alky cycloalkenyl include C-C alkyl as well as those optional 15 lamino, di(C-C)alkylaminocarbonyl-N-(C-C)alky Substituents given above for an alkyl moiety. lamino, arylaminocarbonyl-N-(C-C)alkylamino where Carbocyclic rings include aryl, cycloalkyl and cycloalk the aryl group is substituted by C-C alkyl or halogen) and enyl groups.
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