Herbicidally active heteroaryl-substituted cyclic diones or derivatives tliereof The present invention relates to novel, herbicidally active heteroaryl diones or derivatives thereof, specifically herbicidally active heteroaryl-substituted cyclic diones or derivatives thereof, more specifically herbicidally active 2-heteroaryl-cyclopentane-1,3-diones or derivatives thereof; to processes for the preparation of these compounds or derivatives; to compositions comprising these compounds or derivatives; and to their use in controlling weeds, especially in crops of useful plants, or in inhibiting undesired plant growth. Heteroaryl cyclic dione compounds having herbicidal action are described in US 4,678,501. WO 96/16061 A1 (Bayer AG) discloses thiophene-substituted cyclic diones, wherein the cyclic dione is selected from one of eight heterocyclic or carbocyclic classes such as cyclopentanedione or cyclohexanedione. and the use of these diones as pesticides and herbicides. WO 02/088098 A1 (Bayer AG) discloses thiazolyl-substituted carbocyclic 1,3-diones, specifically 2-(thiazolyl)-cyclopentane-1,3-diones and 2-(thia2olyl)-cyclohexane- 1,3-diones, and derivatives thereof, and their uses as pesticidal agents, herbicides, and fungicides. WO 03/035643 A1 (Bayer Cropscience AG) discloses 5-membered-heterocycles substituted by oxo and also substituted by either N-linked-pyrazolyl or C- linked-pyrazolyl, and their uses as phytosanilary products, microbicides, and herbicides. WO 2009/000533 A1 (Syngenta Limited) discloses inter alia pyrandione, thiopyrandione and cyclohexanetrione compounds, which are substituted by an optionally substituted monocyclic or bicyclic heteroaromatic ring such as thiophene or thiazolyl, and their use as herbicides. WO 2009/015877 A1 (Syngenta Limited) discloses bicyclic (bridged carbocyclic) diones, which are substituted by an optionally substituted monocyclic or bicyclic heteroaromatic ring such as thiophene or thiazolyl, and their use as herbicides. WO 2009/086041 A1 (E.I. DuPonl de Nemours & Co.) discloses herbicidal pyridazinone derivatives substituted by -G-J where G and J are each independently an optionally substituted phenyl ring or an optionally substituted 5- or 6-membered heteroaromatic ring; in WO 2009/086041, G can for example be substituted 1H-pyrazol-1-yl. US 4,338,122 (Union Carbide Corp.) discloses 2-aryl-1,3-cyclopentanedione compounds exhibiting acaricidal and herbicidal activity. WO 96/01798 (Bayer AG) and its derived patent US 5,840,661 disclose 2-aryl-cyclopentane-1,3-dione derivatives and their use as pesticides and herbicides. WO 01/74770 (Bayer AG), its equivalent US 2003/0216260 A1, and its derived AU patent 782557 (AU 200144215C) disclose C2-phenyl-substituted cyclic (heterocyclic or carbocyclic) ketoenols and their use as pesticides and herbicides. WO - 2 - 2008/071405 A1 (Syngenta Limited et al.) discloses inter alia pyrandione, thiopyrandione and cyclohexanetrione compounds, which are substituted by a phenyl ring which is substituted by optionally substituted aryl or optionally substituted heteroaryl, and their use as herbicides. WO 2008/145336 A1 (Syngenta Limited) discloses bicyclic (bridged carbocyclic) diones, which are substituted by a substituted phenyl ring, and their use as herbicides. Copending patent application PCT/EP2009/058250, filed on 1 July 2009 and published on 7 January 2010 as WO 2010/000773 Al (Syngenta Limited), discloses 5-(heterocyclylalkyl)-3- hydroxy-2-phenyl-cyclopent-2-enones, and their 2-phenyl-4-(heterocyclylalkyl)-cyclopentane- 1,3-dione tautomers, and derivatives thereof, as herbicides. Copending patent application PCT/EP2009/066712, filed on 9 December 2009 and published on 24 June 2010 as WO 2010/069834 Al (Syngenta Participations AG and Syngenta Limited), discloses 2-phenyl-4- (heteroarylmethyl)-cyclopentane-1,3-diones, and derivatives thereof as herbicides. Novel heteroaryl dione compounds and derivatives thereof, having herbicidal and/or plantgrowth- inhibiting properties, have now been found. The present invention accordingly relates to a compound of formula (I) OG RI i yOm f^1 O 5 4 R R (I). wherein: G is hydrogen or an agriculturally acceptable metal, sulfonium, ammonium or latentiating group; and R\ R^ R^. R" and R^ are independently hydrogen, halogen, d-Cealkyl. Ci-CehaloalkyI, Ci- Cealkoxy, Ci-Cehaioalkoxy, C2-C6alkenyl, Cz-Cehaloalkenyl. Ca-Cealkynyl, Ca-Cealkenyloxy, Ca-Cehaloalkenyloxy, Ca-Cealkynyloxy, Ca-CecycloalkyI, Ci-Cealkylthio, Ci-Cealkylsulfinyl, Ci- Cealkylsulfonyl, Ci-Cehaloalkylsulfonyl. Ci-Cealkoxysulfonyl, Ci-Cehaloalkoxysulfonyl, cyano. nitro, phenyl, phenyl substituted by C,-C4alkyl, Ci-CahaloalkyI, Ci-Caalkoxy, Ci-Cahaloalkoxy, cyano. nitre, halogen, d-Caalkylthio, Ci-Caalkylsulfinyl or Ci-Caalkylsulfonyl, or heteroaryl or - 3 - heteroaryl substituted by Ci-C4alkyl, Ci-C3haloalkyl, d-Csalkoxy, Ci-Cahaloalkoxy, cyano, nitro, halogen, Ci-Caalkylthio, d-Caalkylsulfinyl or Ci-Caalkylsulfonyl, or benzyl or benzyl substituted by Ci-C4alkyl, Ci-CahaloalkyI, d-Csalkoxy, Ci-Cshaloalkoxy, cyano, nitro, halogen, C-Caalkylthio. CrCsalkylsulfinyl or Ci-Caalkylsulfonyl, or Ca-CecycloalkylCi-Csaikyl in which a ring or chain methylene group is optionally replaced by an oxygen or sulfur atom; and/or R^ and R^ or R" and R^ together with the carbon atoms to which they are attached form an optionally substituted 3- to 8-membered ring, optionally containing an oxygen, sulphur or nitrogen atom; and/or R^ and R" together form a bond; and Q is C3-C8 saturated or mono-unsaturated heterocyclyl containing at least one heteroatom selected from O, N and S, unsubstituted or substituted by a residue of formula =0, =N-R^°, CrC4alkyl, Ci-C4haloalkyl, Ci-C4alkoxyCi-C2alkyl, Ca-CecycloalkyI, phenyl or phenyl substituted by C,-C4alkyl, Ci-CahaloalkyI, Ci-Csalkoxy, Ci-Cahaloalkoxy, cyano, nitro. halogen, Ci-Caalkylthio, Ci-Caalkylsulfinyl or Ci-Caalkylsulfonyl, where R^° is Ci-CealkyI, C,- Cehaloalkyi, Ca-C/cycloalkyI, Ci-Cealkoxy, Ci-Cehaloalkoxy, Ci-Cealkylsulfinyl, Ci- Cealkylsuifonyl, Ci-C6alkylcart>onyl, Ci-Cehaloalkylcarbonyl, C-Cealkoxycarbonyl, Ci- Cealkylaminocarbonyl, C2-C8dialkylaminocarbonyl, Ci-Cehaloalkylsulfinyl or d - Cehaloalkylsulfonyl; or Q is an heteroaryl or heteroaryl substituted by Crdalkyl, Ci-Cahaioalkyi, d-Caalkoxy, Ci- Cahaloalkoxy, cyano, nitro, halogen, Ci-Caalkylthio, Ci-Caalkylsulfinyl or Ci-Csalkylsulfonyl; and m is 1, 2 or 3; and Het is an optionally substituted monocyclic or bicydic heteroaromatic ring; wherein, in the optionally substituted monocyclic or bicydic heteroaromatic ring which is Het, the optional substituents are selected, independently, from halogen, nitro, cyano, rhodano, isothiocyanato, CrCealkyI, d-CehaloalkyI, d-C6alkoxy(CrC6)alkyl, C2-C6alkenyl, C2- Cehaloalkenyl, C2-C6alkynyl, Ca-dcycloalkyi (itself optionally substituted with d-Cealkyi or halogen), Cs-ycycloalkenyl (itself optionally substituted with Ci-CealkyI or halogen), hydroxy, Ci-Cioalkoxy, d-doalkoxy(Ci-do)alkoxy, tri(d-C4)alkylsilyl(d-C6)alkoxy, Ci- C6alkoxycarbonyl(d-do)alkoxy, Ci-Ciohaloalkoxy, aryl(d-C4)alkoxy (where the aryl group is optionally substituted with halogen or Ci-CealkyI), Ca-Cycycloalkyloxy (where the cycloalkyi group is optionally substituted with Ci-Cealkyl or halogen), Ca-doalkenyloxy, C3- - 4 - Cioalkynyloxy, mercapto, Ci-Cioalkylthio, Ci-Ciohaloalkylthio, aryl(Ci-C4)alkylthio, C3- Crcycloalkylthio (where the cycloalkyi group is optionally substituted with Ci-CealkyI or halogen). tri(Ci-C4)-alkylsilyl(Ci-C6)alkylthio. arylthio. d-Cealkylsulfonyl, C,- Cehaloalkylsulfonyl, C-Cealkylsulfinyl, Ci-Cehaloalkylsulfinyl, arylsulfonyl, tri(Ci-C4)alkylsilyl. aryldl(CrC4)alkylsllyl, C,-C4alkyldiarylsilyl, triarylsilyl, Ci-Cioalkylcarbonyl, HO2C, C,- Cioalkoxycarbonyl, aminocarbonyl, Ci-Cealkylaminocarbonyl, di(Ci-C6alkyl)-aminocarbonyl, A/-(Ci-C3 alkyl)-/V-{Ci-C3alkoxy)aminocarbonyl, Ci-Cealkylcarbonyloxy, arylcarbonyloxy, di(Ci-C6)alkylaminocarbonyloxy, aryl (itself optionally substituted with Ci-CealkyI or halogen), heteroaryl (itself optionally substituted with CrCealkyI or halogen), heterocyclyl (itself optionally substituted with Ci-CealkyI or halogen), aryloxy (where the aryl group is optionally substituted with Ci-CealkyI or halogen), heteroaryloxy (where the heteroaryl group is optionally substituted with Ci-CealkyI or halogen), heterocyclyloxy (where the heterocyclyl group is optionally substituted with Ci-CealkyI or halogen), amino, Ci-Cealkylamino, di(Ci- C6)alkylamino, Ci-Cealkylcarbonylamino, N-(Ci-C6)alkylcarbonyl-N-(Ci-C6)alkylamino, and arylcarbonyl (where the aryl group is itself optionally substituted with halogen or Ci-CealkyI); or two adjacent positions on the Het heteroaromatic system are optionally cyclised to fonn a 5, 6 or 7 membered carbocyclic or heterocyclic ring, itself optionally substituted with halogen or d-Cealkyl; or, in the optionally substituted monocyclic or bicyclic heteroaromatic ring which is Het, the optional substituents are selected from arylcarbonylamino (where the aryl group is substituted by Ci-CealkyI or halogen), (Ci-C6)alkoxycarbonylamino, (Ci- C6)alkoxycarbonyl-A/-(C,-C6)alkylamino, aryloxycarbonylamino (where the aryl group is substituted by Ci-CealkyI or halogen), aryloxycarbonyl-A/-(Ci-C6)alkylamino, (where the aryl group is substituted by Ci-CealkyI or halogen), arylsulphonylamino (where the aryl group is substituted by Ci-CealkyI or halogen), arylsulphonyl-A/-(CrC6)alkylamino (where the aryl group is substituted by Ci-CealkyI or halogen), aryi-N-(Ci-C6)alkylamino (where the aryl group is substituted by Ci-CealkyI or halogen), arylamino (where the aryl group is substituted by Ci-CealkyI or halogen), heteroaryl amino (where the heteroaryl group is substituted by Cr Csalkyl or halogen), heterocyclylamino (where the heterocyclyl group is substituted by d - Cealkyl or halogen), aminocarbonylamino, Ci-Cealkylaminocarbonylamino, di(Ci- C6)alkylaminocarbonylamino, arylaminocarbonylamino (where the aryl group is substituted by Ci-CealkyI or halogen), aryl-A/- (Ct-C6)alkylaminocarbonylamino (where the aryl group is substituted by Ci-CealkyI or halogen). Ci-C6alkylaminocarbonyl-/V-(Ci-C6)alkylamino, di(Ci- CB)alkylaminocarbonyl-A/-( CrC6)alkylamino, arylaminocarbonyl-/V-(Ci-C6)alkylamino (where - 5 - the aryl group is substituted by Ci-C6allR^ -SO2-R*, -P(X*XR')-R^ and CHa-X'-R^ wherein X', X''. X*^, X"*, X^ and X' are independently of each other oxygen or sulfur; and wherein R' is H, Ci-CisalkyI (e.g. Ci-CealkyI or CrC4atkyl such as terf-butyl or isopropyl), Ca-Ciealkenyl, C2-Ci8alkynyl, d-Ciohaloalkyl (e.g. Ci-Ciofiuoroalkyi). Ci- Ciocyanoalkyl, Ci-Cionitroalkyl. Ci-Cioaminoalkyl, Ci-C5alkylamino(Ci-C5)alkyl, C2- C8dialkylamino(Ci-C5)alkyl. C3-C7cycloalkyl(Ci-C5)alkyl. CrC5alkoxy(Ci-C5)alkyl, C3- C5alkenyloxy(Ci-C5)alkyl, Ci-C5alkylthio(Ci-C5)alkyl, Ci-C5alkylsulfinyl(Ci-C5)alkyl, Ci- C5alkylsulfonyl(CrC5)alkyl. C2-C8alkylideneaminoxy(Ci-C5)alkyl, CrCsalkyicarbonyKCr C5)alkyl, Ci-C5alkoxycarbonyl(CrC5)alkyl, aminocarbonyl(CrC5)alkyl, d - C5alkylaminocarbonyl(Ci-C5)alkyl, C2-C8dialkylaminocarbonyl(d-C5)alkyl, d - C5alkylcarbonylamino(CrC5)alkyl, A/-(d-d)alkylcarbonyl-A/-(Ci-C5)alkylamino(d-C5)alkyl, C3-C6trialkylsilyl(Ci-C5)alkyl, phenyl(d-C5)alkyl (wherein the phenyl is optionally substituted by Ci-dalkyl, d-CahaloalkyI, Ci-Caalkoxy, d-dhaloalkoxy, d-Caaikylthio, d - dalkylsulfinyl, d-Caalkylsulfonyl, halogen, cyano, or by nitro), heteroaryl(Ci-C5)alkyl (wherein the heteroaryl is optionally substituted by Ci-CaaikyI, Ci-CahaloalkyI, Ci-Caalkoxy, d-dhaloalkoxy, d-dalkylthio, d-Caalkylsulfinyl, Ci-Caalkylsulfonyl, halogen, cyano, or by nitro), d-Cshaloalkenyl, Ca-CacycloalkyI, or phenyl or phenyl substituted by d-dalkyi, Cr dhaloalkyl, Ci-Caalkoxy. Ci-dhaloalkoxy, halogen, cyano or nitro, or heteroaryl or heteroaryl substituted by C i - d alkyl, Ci-dhaloalkyl, d-dalkoxy, CrCahaloalkoxy, halogen, cyano or nitro; R** is Ci-CisalkyI (e.g. Ci-CealkyI or Ci-C4alkyl such as Ci-CzalkyI), Cs-Cisalkenyl, d - Ciaaikynyl, d-Ciohaloalkyl (e.g. d-Ciofluoroalkyl), Ci-Ciocyanoalkyl, Ci-Cionitroalkyl, d - Cioaminoalkyl, Ci-dalkylamino(Ci-d)alkyl, C2-ddialkylamino(Ci-C5)alkyl, C3- - 7 - C7cycloalkyl(Ci-C5)alkyl, CrC5alkoxy(CrC5)alkyl. C3-C5alkenyloxy(Ci-C5)alkyl, C3- C5alkynyloxy(Ci-C5)alkyl, CrC5alkylthio(Ci-C5)alkyl. Ci-C5alkylsulfinyl(CrC5)alkyl, d - C5alkylsulfonyl(Ci-C5)alkyl. C2-C8aIkylideneaminoxy(CrC5)alkyl, CrCsalkylcarbonylCd- C5)alkyl, Ci-C5alkoxycarbonyl(CrC5)alkyl, aminocarbonyl(Ci-C5)alkyl. d - C5alkylaminocarbonyl(CrC5)alkyl, C2-C8dialkylaminocarbonyl(Ci-C5)alkyl, Cr C5alkylcarbonylamino(Ci-C5)alkyl. W-(C,-C5)alkylcarbonyl-/V-(Ci-C5)alkylamino(CrC5)alkyl, C3-C6trialkylsilyl(Ci-C5)alkyl, phenyl(Ci-C5)alkyl (wherein the phenyl is optionally substituted by d-Csalkyl. CrCshaloalkyI, d-Csalkoxy, d-Cahaloalkoxy. d-Caalkylthio, d - Caalkylsulfinyl, d-Caalkylsulfonyl, halogen, cyano, or by nitro), heteroaryld-CsalkyI, (wherein the heteroaryl is optionally substituted by Ci-Caalkyl. Ci-CshaloalkyI, d-C3alkoxy, Ci- Cshaloalkoxy, Ci-Csalkyl-thio, Ci-Csalkylsulfinyl, Ci-Csalkylsulfonyl. halogen, cyano, or by nitro), Cs-Cshaloalkenyl. C3-C8cycloalkyl. or phenyl or phenyl substituted by d-Csalkyl, d - Cshaloalkyl, d-Csalkoxy, Ci-Cshaloalkoxy. halogen, cyano or nitro, or heteroaryl or heteroaryl substituted by C1-C3 alkyl, d-C3haloalkyl, Ci-Csalkoxy, d-C3haloalkoxy, halogen, cyano or nitro; R'^ and R" are each independently of each other hydrogen, Ci-CioalkyI (e.g. Ci-CealkyI or Cidalkyl such as d-Cjalkyl), C3-doalkenyl, Cs-doalkynyl, d-CiohaloalkyI (e.g. C2- Ciofluoroalkyl), Ci-Ciocyanoalkyl, d-Cionitroalkyl, Ci-Cioaminoalkyl, CrC5alkylamino(Ci- C6)alkyl, C2-C8dialkylamino(d-C5)alkyl, C3-C7cycloalkyl(d-C5)alkyl, d-C5alkoxy(d-d)alkyl, C3-C5alkenyloxy(Ci-C5)alkyl, C3-C5alkynyloxy(CrC5)alkyl, d-C5alkylthio(CrC5)alkyl, Ci- C5alkylsulfinyl(d-C5)alkyl, d-dalkylsulfonyl(Ci-C5)alkyl, C2-C8alkylideneaminoxy(d- C5)alkyl, Ci-dalkylcarbonyl(d-C5)alkyl, d-C5alkoxycarbonyl(Ci-C5)alkyl, aminocarbonyl(d- C6)alkyl, d-C5alkylaminocarbonyl(Ci-C5)alkyl, d-C8dialkylaminocarbonyl(Ci-C5)alkyl, Ci- C5alkylcarbonylamino(d-C5)alkyl. /S/-(d-C5)alkylcarbonyl-A/-(C2-C5)alkylaminoalkyl, d - dtrialkylsilyl(Crd)alkyl, phenyl(Ci-C5)alkyl (wherein the phenyl is optionally substituted by d-Caalkyl, Ci-Cshaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, Ci-Csalkylsulfinyl. Ci-Caalkylsulfonyl, halogen, cyano, or by nitro), heteroaryl(Ci-C5)alkyl (wherein the heteroaryl is optionally substituted by d-dalkyi, Ci-CshaloalkyI, Ci-dalkoxy, Ci-Cshaloalkoxy, Ci- Csalkylthio, Ci-Csalkylsulfinyl, Ci-Csalkylsulfonyl, halogen, cyano, or by nitro), C2- Cshaloalkenyl, Cs-CacycloalkyI, or phenyl or phenyl substituted by Ci-CsalkyI, CrCshaloalkyl, Ci-Caalkoxy, d-Cshaloalkoxy, halogen, cyano or nitro, or heteroaryl or heteroaryl substituted by d-CaalkyI, Ci-Cshaloalkyl, d-Csalkoxy, d-Cshaloalkoxy, halogen, cyano or nitro, or heteroarylamino or heteroarylamino substituted by d-CaalkyI, Ci-Cshaloalkyl, Ci-Csalkoxy, Ci-Cahaloalkoxy, halogen, cyano or nitro, or diheteroarylamino or diheteroarylamino - 8 - substituted by Ci-Caalkyl. Ci-CshaloalkyI, Ci-Caalkoxy, Ci-Cshaloalkoxy, halogen, cyano or nitre, or phenylamino or phenylamino substituted by Ci-Caaikyl. Ci-Calialoalkyl. Ci-Caalkoxy, Ci-Cahaloalkoxy, halogen, cyano or by nitro, or diphenylamino or diphenylamino substituted by Ci-CaalkyI, Ci-CahaloalkyI, Ci-Caalkoxy, Ci-Cahaloalkoxy, halogen, cyano or by nitro, or Cs-C/cycloalkylamino. di-Ca-C/cycloalkylamino or Cs-Crcycloalkoxy; or R"^ and R" join together to form a 3-7 membered ring, optionally containing one heteroatom selected from O or S; R* is Ci-Cioalkyl (e.g. Ci-CealkyI or Ci-C4alkyl such as Ci-C2alkyl), Ca-Cioalkenyl. C2- Cioalkynyl, Ci-CiohaloalkyI (e.g. Ci-CiofluoroalkyI), C,-Ciocyanoalkyl. Ci-Cionitroalkyl. C,- Cioaminoalkyl, Ci-C5alkylamino(Ci-C5)alkyl, C2-C8dialkylamino(Ci-C5)alkyl, C3- C7cycloalkyl(C,-C5)alkyl. Ci-C5alkoxy(Ci-C5)alkyl, C3-C5alkenyloxy(C,-C5)alkyl, C3- C5alkynyloxy(C,-C5)alkyl. C,-C5alkylthio(C,-C5)alkyl. CrC5alkylsulfinyl(C,-C5)alkyl, C,- C5alkylsulfonyl(Ci-C5)alkyl. C2-C8alkylideneaminoxy(Ci-C5)alkyl, Ci-C5alkylcarbonyl(Ct- C5)alkyl, Ci-C5alkoxycarbonyl(Ci-C5)alkyl, aminocarbonyl(Ci-C5)alkyl, C,- C5alkylaminocarbonyl(Ci-C5)aikyl, C2-C8dialkylaminocarbonyl(Ci-C5)alkyl, d - C5alkylcarbonylamino(Ci-C5)alkyl, A/-(Ci-C5)alkylcarbonyl-A/-(Ci-Cs)alkylamino(Ci-C5)alkyl, C3-C6trialkylsilyl(Ci-C5)aikyi, phenyl(C,-C5)alkyl (wherein the phenyl is optionally substituted by Ci-Csalkyl. Ci-CshaloalkyI, Ci-C3alkoxy, Ci-Cshaloalkoxy, Ci-C3alkylthio, Ci- Csalkylsulfinyl, Ci-Csaikylsulfonyl. halogen, cyano, or by nitro), heteroaryl(Ci-C5)alkyl (wherein the heteroaryl is optionally substituted by Ci-CsalkyI, Ci-C3haloalkyl, Ci-C3alkoxy, Ci-Cshaloalkoxy, Ci-Csalkylthio, Ci-Csalkylsulfinyl, Ci-Csalkylsulfonyl, halogen, cyano, or by nitro), C2-C5haloalkenyl, Cs-CecycloalkyI, or phenyl or phenyl substituted by Ci-CsalkyI, Ci- C3haloalkyl, Ci-Caalkoxy, Ci-Cahaloalkoxy, halogen, cyano or nitro, or heteroaryl or heteroaryl substituted by Ci-C3alkyl, Ci-CahaloalkyI, Ci-C3alkoxy, Ci-Cshaloalkoxy, halogen, cyano or by nitro, or heteroarylamino or heteroarylamino substituted by C1-C3 alkyl, Ci- Cshaloalkyl, Ci-Caalkoxy, Ci-Cahaloalkoxy, halogen, cyano or by nitro, or diheteroarylamino or diheteroarylamino substituted by Ci-CaalkyI, Ci-Cshaloalkyl, Ci-C3alkoxy, Ci-C3haloalkoxy, halogen, cyano or nitro, or phenylamino or phenylamino substituted by Ci-CaalkyI, Ci- Cshaloalkyl, Ci-Caalkoxy, CrCahaloalkoxy, halogen, cyano or nitro, or diphenylamino or diphenylamino substituted by Ci-CaalkyI, Ci-CahaloalkyI, Ci-Caalkoxy, Ci-Cahaloalkoxy, halogen, cyano or nitro, or Ca-CTCycloalkylamino, diCa-CTcycloalkylamino, Cs-CTcycloalkoxy, Ci-Cioalkoxy, d-Ciohaloalkoxy, Ci-Csalkylamino or C2-C6dialkylamino; - 9 - R' and R^ are are each independently of each other Ci-Cioalkyl (e.g. Ci-CealkyI or Ci-C4alkyl such as Ci-C2alkyl), Cz-Cioalkenyl. C2-Cioalkynyl, CrCioalkoxy, Ci-CiohaloalkyI (e.g. Ci- Ciofluoroalkyl), Ci-CiocyanoalkyI, Ci-Cionitroalkyl, Ci-Cioaminoalkyl, Ci-C5alkylamino(Ci- C5)alkyl, C2-C8dialkylamino(CrC5)alkyl, C3-C7cycloalkyl(Ci-C5)alkyl, Ci-C5alkoxy(Ci-C5)alkyl, C3-C5alkenyloxy(Ci-C5)alkyl. C3-C5alkynyloxy(Ci-C5)alkyl, Ci-C5alkylthio(CrC5)alkyl, C,- C5alkylsulfinyl(Ci-C5)alkyl. CrC5alkylsulfonyl(Ci-C5)alkyl. C2-C8alkylideneaminoxy(Cr C5)alkyl. Ci-C5alkylcarbonyl(Ci-C5)alkyl, Ci-C5alkoxycarbonyl(Ci-C6)alkyl, aminocarbonyl(Ci- C5)alkyl. Ci-C5alkylaminocarbonyl(Ci-C5)alkyl. C2-C8dialkylaminocart>onyl(Ci-C5)alkyl, Ci- C5alkylcarbonylamino(Ci-C5)alkyl, A/-(Ci-C5)alkylcarbonyl-A/-(C2-C5)alkylaminoalkyl. C3- C6trialkylsilyl(Ci-C5)alkyl, phenyl(Ci-C5)alkyl (wherein the phenyl is optionally substituted by d-Csalkyl. Ci-CshaloalkyI, Ci-C3alkoxy, Ci-Cshaloalkoxy, Ci-Csalkylthio. Ci-Csalkylsulfinyl, Ci-Caalkylsulfonyl, halogen, cyano. or by nitro). heteroaryl(Ci-C5)alkyl (wherein the heteroaryl is optionally substituted by Ci-C3alkyl, Ci-CshaloalkyI, Ci-Caalkoxy, Ci-Cshaloaikoxy, Ci- C3alkylthio, Ci-Csalkylsulfinyl, C-Csalkylsulfonyl, halogen, cyano, or by nitro), C2- Cshaloalkenyl, Cs-CscycloalkyI, or phenyl or phenyl substituted by Ci-CsalkyI, Ci-Cshaloalkyl, Ci-Csalkoxy, Ci-C3haloalkoxy, halogen, cyano or nitro, or heteroaryl or heteroaryl substituted by C1-C3 alkyl, Ci-CshaloalkyI, Ci-C3alkoxy. Ci-Cshaloalkoxy. halogen, cyano or by nitro, or heteroarylamino or heteroarylamino substituted by C1-C3 alkyl, Ci-CshaloalkyI, Ci-C3alkoxy, Ci-Cshaloalkoxy. halogen, cyano or by nitro, or diheteroarylamino or diheteroarylamino substituted by C1-C3 alkyl. Ci-CshaloalkyI, Ci-Caalkoxy, Ci-Cshaloalkoxy, halogen, cyano or nitro, or phenylamino or phenylamino substituted by C-CsalkyI, Ci-CshaloalkyI, Ci-Csalkoxy, Ci-Cahaloalkoxy, halogen, cyano or nitro, or diphenylamino or diphenylamino substituted by Ci-CsalkyI, Ci-C3haloalkyl, Ci-C3alkoxy, Ci-Cahaloalkoxy, halogen, cyano or nitro, or Cs-Cycycloalkylamino, diC3-C7cycloalkylamino, C3-C7cycloalkoxy, Ci-Ciohaloalkoxy, Ci- Csalkylamino or C2-C8dialkylamino, or benzyloxy or phenoxy, wherein the benzyl and phenyl groups are in turn optionally substituted by Ci-CsalkyI, Ci-Cshaioalkyl, Ci-Csalkoxy, Ci- Cshaloalkoxy, halogen, cyano or nitro; and R** is C-Cioalkyl (e.g. d-Cealkyl or CrC4alkyl such as Ci-CzalkyI), Cs-Cioalkenyl, C3- Cioalkynyl, Ci-Ciohaloalkyl (e.g. Ci-Ciofluoroalkyl), C,-Ciocyanoalkyl, Ci-Cionitroalkyl, C2- Cioaminoalkyl, Ci-C5alkylamino(Ci-C5)alkyl, C2-C8dialkylamino(CrC5)alkyl, C3- C7cycloalkyl(Ci-C5)alkyl, Ci-C5alkoxy(Ci-C5)alkyl, C3-C5alkenyloxy(Ci-C5)alkyl, C3- C5alkynyloxy(Ci-C5)alkyi, Ci-C5alkylthio(C,-C5)alkyl, Ci-C5alkylsulfinyl(Ci-C5)alkyl, C,- C5alkylsulfonyl(Ci-C5)alkyl, C2-C8alkylideneaminoxy(CrC5)aikyl, Ci-CsalkylcarbonyKCi- C5)alkyl, Ci-C5alkoxycarbonyl(Ci-C5)alkyl, aminocarbonyl(Ci-C5)alkyl, Ci- 10- C5alkylaminocarbonyl(CrC5)alkyl, C2-C8dialkylaminocarbonyl(Ci-C5)alkyl, Ci- C5alkylcarbonylamino(Ci-C5)alkyl, /\/-(Ci-C5)alkylcarbonyl-A/-(Ci-C5)alkylamino(Ci-C5)alkyl, C3-C6trialkylsilyl(CrC5)alkyl, phenyl(Ci-C5)alkyl (wherein wherein the phenyl is optionally substituted by Ci-CaalkyI, d-Cshaloalkyl, Ci-Csalkoxy, Ci-Cahaloalkoxy, Ci-Caalkylthio. Ci- Caalkylsulfinyl. C1-C3 alkylsulfonyl, halogen, cyano or by nitro), heteroaryl(Ci-C5)alkyi (wherein the heteroaryl is optionally substituted by Ci-CsalkyI, Ci-Cahaloaikyl, Ci-Caalkoxy, Ci-Cahaloalkoxy, Ci-Csalkylthio, Ci-Caalkylsulfinyl, C1-C3 alkylsulfonyl, halogen, cyano or by nitro), phenoxy(Ci-C5)alkyl (wherein the phenyl is optionally substituted by Ct-CaalkyI, Ci- Cahaloaikyi, Ct-Caalkoxy, Ci-Cahaloalkoxy, Ci-Caalkylthio, Ci-Csalkylsulfinyl. C1-C3 alkylsulfonyl, halogen, cyano or by nitro), heteroaryloxy(Ci-C5)alkyl (wherein the heteroaryl is optionally substituted by Ci-CaalkyI, Ci-CshaloalkyI, Ci-Csalkoxy, Ci-Cshaloalkoxy, C,- Csalkylthio, Ci-C3alkylsulfinyl, C1-C3 alkylsulfonyl, halogen, cyano or by nitro), C3- Cshaloalkenyl, Ca-CecycioalkyI, or phenyl or phenyl substituted by Ci-CsalkyI, Ci-CahaloalkyI, Ci-Csalkoxy, Ci-C3haloalkoxy, halogen or by nitro, or heteroaryl or heteroaryl substituted by Ci-CaalkyI, Ci-Cshaloalkyi, Ci-Caalkoxy, Ci-Cshaloalkoxy, halogen, cyano or by nitro; and wherein the compound is optionally an agronomically acceptable salt thereof. In the substituent definitions of the compounds of the formula I, each alkyl moiety either alone or as part of a larger group (such as alkoxy, alkylthio, alkoxycarbonyl, alkylcarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or cycloalkylalkyi) is a straight or branched chain and is, for example, independently methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, isopropyi, n-butyl, sec-butyl, isobutyl, fe/t-butyl or neopentyl. The alkyl groups are suitably Ci-CealkyI groups, but are preferably Ci-C4alkyl or Ci-C3alkyl groups, and, more preferably, Ci-C2alkyl groups. Alkenyl and alkynyl moieties can be in the form of straight or branched chains, and the alkenyl moieties, where appropriate, can be of either the (E)- or (Z)-configuration. Examples are vinyl, aliyl and propargyl. Alkenyl and alkynyl moieties can contain one or more double and/or triple bonds in any combination. It is understood, that allenyl is included in these terms. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine. - 1 1 - Haloalkyl (e.g. fluoroalkyl) groups are alkyl groups which are substituted with one or more of the same or different halogen (e.g. fluorine) atoms and are suitably, independently, CF3, CF2CI, CF2H. CCI2H. FCH2. CICH2, BrCH2. CH3CHF, (CH3)2CF, CF3CH2 or CHF2CH2; preferably, independently, CF3. CF2H, FCH2. CH3CHF, (CH3)2CF, CF3CH2 or CHF2CH2. The terms "heteroaryl" and/or "heteroaromatic" preferably refer to an aromatic ring system containing at least one heteroatom and consisting either of a single ring or of two or more fused rings. Preferably, single rings will contain up to three heteroatoms and bicyclic systems up to four heteroatoms which will preferably be chosen from nitrogen, oxygen and sulphur. Examples of such groups include independently furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyi, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl. 1,2,3-triazinyi. 1,2,4-triazinyl, 1,3,5-tria2inyl, benzofuryl, benzisofuryl, benzothienyl, benzisothienyl, indolyl, isoindolyl, indazolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl, 2,1,3-benzoxadiazole, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl, pteridinyl or indolizinyl. Preferred examples of heteroaromatic radicals include independently pyridyl, pyrimidinyl, triazinyl, thienyl, furyl, oxazolyl, isoxazolyl, 2,1,3-benzoxadiazolyl or thiazolyl. Another group of preferred heteroaryls comprises independently pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl or quinoxalinyl. The term "heterocyclyl" preferably refers to a non-aromatic preferably monocyclic or bicyclic ring systems containing up to 7 atoms including one or more (preferably one or two) heteroatoms selected from O, S and N. Examples of such rings include 1,3-dioxolane, oxetane, tetrahydrofuran, tetrahydropyran, morpholine, thiomorpholin and piperazine. When present, the optional substituents on heterocyclyl include Ci-CealkyI and Ci-CehaloalkyI as well as those optional substituents given above for an alkyl moiety. CycloalkyI includes preferably independently cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. CycloalkylalkyI is preferentially cyclopropylmethyl. -12- Carbocyclic rings include independently aryl, cycloalkyi or carbocyclic groups, and cycloalkenyl groups. In the compounds of the formula I, each aryl group, either alone or as part of a larger group (e.g. aryloxy etc.), is independently preferably phenyl. When present, the optional substituents on aryl (preferably phenyl), heteroaryl and/or carbocycles are preferably selected, independently, from hatogen, nitro, cyano, rhodano, isothiocyanato, Ci-Cealkyl. Ci-Cehaloalkyi, Ci-C6alkoxy(Ci-C6)aikyl, C2-C6alkenyl, C2- Cehaloalkenyl, CrCealkynyl, Ca-C/cycioalkyl (itself optionally substituted with Ci-Ceaikyl or halogen), Cs-ycycloaikenyl (itself optionally substituted with Ci-CealkyI or halogen), hydroxy, Ci-Cioalkoxy, Ci-C,oalkoxy(Ci-C,o)alkoxy, tri(Ci-C4)alkylsiIyl(Ci-C6)alkoxy, d - C6alkoxycarbonyl(Ci-Cio)alkoxy, Ci-Ciohaloalkoxy, aryl(Ci-C4)alkoxy (where the aryl group is optionally substituted with halogen or Ci-CealkyI), Ca-Cycycioalkyloxy (where the cycloalkyi group is optionally substituted with Ci-CealkyI or halogen), Ca-Cioalkenyloxy, C3- Cioalkynyloxy, mercapto, Ci-Cioalkylthio, Ci-Ciohaloalkylthio, aryl(Ci-C4)alkylthio, C3- Cycycloalkylthio (where the cycloalkyi group is optionally substituted with Ci-CealkyI or halogen), tri(Ci-C4)-alkylsilyl(Ci-C6)alkylthio, arylthio, Ci-Cealkylsulfonyl, Ci- Cehaloalkylsulfonyl, Ci-Cealkylsulfinyl, CrCehaloalkylsulfinyl, arylsulfonyl, tri(Ci-C4)alkylsilyl, aryldi(Ci-C4)alkylsilyl, Ci-C4alkyldiarylsilyl, triarylsilyl, Ci-Cioalkylcarbonyl, HO2C, d - Cioalkoxycarbonyl, aminocarbonyl, Ci-Cealkylaminocarbonyl, di(Ci-C6alkyl)-aminocarbonyl, A/-(Ci-C3 alkyl)-A/-(Ct-C3alkoxy)aminocarbonyl, Ci-Cgalkylcarbonyloxy, arylcarbonyloxy, di(Ci-C6)alkylaminocarbonyloxy, aryl (itself optionally substituted with Ci-CealkyI or halogen), heteroaryl (itself optionally substituted with Ci-CealkyI or halogen), heterocyclyl (itself optionally substituted with Ci-CealkyI or halogen), aryloxy (where the aryl group is optionally substituted with Ci-CealkyI or halogen), heteroaryloxy (where the heteroaryl group is optionally substituted with Ci-CealkyI or halogen), heterocyclyloxy (where the heterocyclyl group is optionally substituted with Ci-CealkyI or halogen), amino, Ci-Cealkylamino, di(Ci- C6)alkylamino, Ci-Cealkylcarbonylamino, A/-(Ci-C6)alkylcarbonyl-A/-(Ci-C6)alkylamino. and arylcarbonyl (where the aryl group is itself optionally substituted with halogen or Ci-CealkyI); or two adjacent positions on an aryl or heteroaryl system may be cyclised to form a 5, 6 or 7 membered carbocyclic or heterocyclic ring, itself optionally substituted with halogen or Ci- Cealkyl. Further substituents for aryl or heteroaryl include arylcarbonylamino (where the aryl group is substituted by Ci-CealkyI or halogen), (Ci-C6)alkoxycarbonylamino, (Ci- C6)alkoxycarbonyl-W-(CrC6)alkylamino, aryloxycarbonylamino (where the aryl group is substituted by Ci-CealkyI or halogen), aryloxycarbonyl-A/-(Ci-C6)alkylamino, (where the aryl group is substituted by Ci-CealkyI or halogen), arylsulphonylamino (where the aryl group is -13- substituted by Ci-CealkyI or halogen), arylsulphonyl-A/-(Ci-C6)alkylamino (where the aryl group is substituted by Ci-CealkyI or halogen). aryl-N-(CrC6)alkylamino (where the aryl group is substituted by Ci-CealkyI or halogen), arylamino (where the aryl group is substituted by Ci-Cealkyi or halogen), heteroaryl amino (where the heteroaryl group is substituted by Ci- Cgalkyl or halogen), heterocyclylamino (where the heterocyclyl group is substituted by Ci- Cealkyl or halogen), aminocarbonylamino. Ci-Cealkylaminocarbonylamino, di(Ci- C6)alkylaminocarbonylamino. arylaminocarbonylamino (where the aryl group Is substituted by Ci-CealkyI or halogen), aryl-ZV- (Ci-C6)alkylaminocarbonylamino (where the aryl group is substituted by Ci-Cealkyi or halogen), Ci-C6alkylaminocarbonyl-/\/-(Ci-C6)alkylamino, di(Ci- C6)alkylaminocarbonyl-A/-( C,-C6)alkylamino, arylaminocarbonyl-A/-(Ci-C6)alkylamino (where the aryl group is substituted by Ci-CealkyI or halogen) and aryl-A/-(Ci-C6)alkylaminocarbonyl- A/-(Ci-C6)alkylamino (where the aryl group is substituted by Ci-CsalkyI or halogen). For substituted heterocyclyl groups it is preferred that one or more substituents are independently selected from halogen, Ci-CealkyI, Ci-CehaloalkyI, Ci-Cealkoxy. Ci- Cehaloalkoxy, Ci-Cealkylthio, Ci-Cealkylsulfinyl, Ci-Cealkylsulfonyl, nitro and cyano. It is to be understood that dialkylamino substituents include those where the dialkyi groups together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N or S and which is optionally substituted by one or two independently selected Ci-Cealkyi groups. When heterocyclic rings are formed by joining two groups on an N atom, the resulting rings are suitably pyrrolidine, piperidine, thiomorpholine and morpholine each of which may be substituted by one or two independently selected Ci-CealkyI groups. The invention relates also to the agriculturally acceptable salts which the compounds of formula I are able to form with transition metal, alkali metal or alkaline earth metal bases, amines, quaternary ammonium bases or tertiary sulfonium bases. Among the transition metal, alkali metal or alkaline earth metal salt capable of forming transition metal, alkali metal or alkaline earth metal salts (i.e. where G is a metal), special mention should be made of the hydroxides of copper, iron, lithium, sodium, potassium, magnesium or calcium; and preferably the hydroxides, bicarbonates or carbonates of sodium or potassium. - 1 4 - Examples of amines suitable for ammonium salt formation (i.e. where G is an ammonium) Include ammonia, or primary, secondary or tertiary Ci-Cisalkylamines, C,- C4hydroxyalkylamines or C2-C4alkoxyalkyl-amines, for example methylamine, ethylamine, npropylamine, isopropylamine, the four butylamine isomers, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine. decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, methylhexylamine, methylnonylamine. methylpentadecylamine, methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, di-n-amylamine, di-isoamylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, isopropanolamine. N.Ndiethanolamine, A/-ethylpropanolamine, A/-butylethanolamine, allylamine, n-but-2-enyiamine, n-pent-2-enylamine, 2,3-dimethylbut-2-enylamine, dibut-2-enylamine, rj-hex-2-enylamine, propyienediamine, trimethylamine, triethylamine, tri-n-propylamlne, tri-isopropylamine, tri-nbutylamine, tri-isobutylamine, tri-sec-butylamine, tri-n-amylamine, methoxyethylamine or ethoxyethylamine; or heterocyclic amines, for example pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine or azepine; or primary arylamines, for example anilines, methoxyanilines, ethoxyanilines, o-, m- or p-toluidines, phenylenediamines, benzidines, naphthylamines or o-, m- or p-chloroanilines; but especially triethylamine, isopropylamine or di-isopropylamine. Preferred quaternary ammonium bases suitable for salt formation (i.e. where G is an ammonium) correspond, for example, to the formula [N(Ra Rb Re Rd)]OH, wherein Ra, Rb. Re and Rd are each independently of the others hydrogen or C,-C4alkyl. Further suitable tetraalkylammonium bases with other anions can be obtained, for example, by anion exchange reactions. Preferred tertiary sulfonium bases suitable for salt formation (i.e. where G is a sulfonium) correspond, for example, to the formula (SReRfRgJOH, wherein Re, Rf and Rg are each independently of the others C1-C4 alkyl. Trimethyisulfonium hydroxide is especially preferred. Suitable sulfonium bases may be obtained from the reaction of thioethers, in particular dialkylsulfides, with alkylhalides, followed by conversion to a suitable base, for example a hydroxide, by anion exchange reactions. -15- It should be understood that in those compounds of formula I, where G is a metal, ammonium or suMonium as mentioned above and as such represents a cation, the corresponding negative charge is largely delocalised across the 0-C=C-C=0 unit. The compounds of formula I according to the invention also include hydrates, for example hydrates which may be formed during salt formation. The latentiating group G Is selected to allow its removal by one or a combination of biochemical, chemical or physical processes to afford compounds of formula I where G is H before, during or following (preferably during or following) application to the treated area or plants. Examples of these processes include enzymatic cleavage (e.g. enzymatic cleavage of esters), chemical hydrolysis and photoloysis. Compounds bearing such groups G may, in some cases, offer certain advantage(s), such as: improved penetration of the cuticula of the plants treated; increased tolerance of crops; improved compatibility or stability in formulated mixtures containing other herbicides, herbicide safeners, plant growth regulators, fungicides nd/or insecticides; and/or reduced leaching in soils; in particular improved penetration of the cuticula of the plants treated. In the latentiating group G, preferably, X', X", X', X"*, X" and/or X' are oxygen. More preferably, all of X', X^ X", X^ X* and X' are oxygen. Preferably, the latentiating group G is a group -C(X'')-R' or -C(X'')-X''-R''. More preferably, the latentiating group G is a group -C(X')-R' or -C(X'')-X''-R^ wherein R^ is hydrogen or Ci-CiealkyI (more preferably, hydrogen or Ci-CealkyI, still more preferably C,- Cealkyl, most preferably Ci-C4alkyl such as (ert-butyl or isopropyl), R*" is CrCisalkyl (more preferably, Ci-Cealkyl, still more preferably Ci-C4alkyl such as Ci-C2alkyl), and the meanings of X^ X^'and X*" are as defined above (more preferably, X^ X" and X*^ are oxygen). It is preferred that G is hydrogen, an alkali metal or alkaline earth metal, where hydrogen is especially preferred. -16- Depending on the nature of the substituents. compounds of formula I may exist in different isomeric forms. When G is hydrogen, for example, compounds of formula I may exist in different tautomeric forms (one dione tautomer and two different keto-enol tautomers), as shown in the following scheme: OH O O R V L R^ 11 R^ U ,\/=55>-^Het iN/V-Het ,\/\^Het a—'^ I R-''\, I R'^—\ If Wtn R1 O pf)m ,^1 O pf)m R1 OH R' R' R* R' R* R' This invention covers all such isomers and tautomers and mixtures thereof in all proportions. Also, when substituents contain double bonds, cis- and frans-isomers can exist. These isomers, too, are within the scope of the claimed compounds of the formula I. In a prefeaed group of compounds of the formula (I), R^ is hydrogen, halogen, Ci-CealkyI, C,- Cehaloalkyl, Ci-Cealkoxy or Ci-Cehaloalkoxy, and, more preferably. R' is hydrogen or methyl. In another preferred group of the compounds of the formula (I), R^and R^ independently are hydrogen, halogen, Ci-Cgalkyl, Ci-Cehaloaikyl, Ci-Cealkoxy or Ci-Cehaloalkoxy, and, more preferably, R^and R^ independently are hydrogen or methyl. Preferably, in the compounds of the formula (I), R''and R^ independently are hydrogen, halogen, Ci-CsalkyI, Ci-Cehaloalkyl. Ci-Cealkoxy or CrCehaloalkoxy, and, more preferably, R^and R' independently are hydrogen or methyl. Preferred saturated or mono-unsalurated rings Q are those of formulae Qi to Qior: <«'.-<>* <^'"-i^* '«>.-0'* ""•"O'' '«>.-d O A Q, Q^ Q3 Q4 Q^ <'^>4CX^ ^'^""O-^ ^^^--O^"" '""'^-^^ '''>"-^' 0 / - 1 7 - -.-<>* -"-iy^ -"-fr* -"-«>^H(V* """-CT* ""--O^* """"O'* """"i^* -^fr' ...-Ci^ ..„-<;x^ ...-<;i^ .^^, Q96 R' R' R" Q100 Q97 Q93 Q99 -19- ' ^ t ^ , '"„!-5C '^'cCl, <^'"Xl, <^""^, °'01 °«» °«0 Q,04 Ql05 ..-cr' "^' -^<1 '"'^ O:K o"V. "•' o >r^. ^_^t^^ . , ^ ^ Q1O6 Q,07 R./ ""« Quo Q108 Q1O6 ^ Q.07 wherein: R is hydrogen, halogen, Ci-Ceall^yl, Ci-CehaloalkyI, Ci-Cealkoxy, CrCehaloalkoxy, C2- Ceslkenyl, Ca-Cehaloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, Ca-Cealkenyloxy, C3- Cehaloalkenyloxy, Cs-Cealkynyloxy, Ca-Cecycloalkyi, Ci-Cealkylthio, CrCealkylsulfinyl, Ci- Cealkylsulfonyl, Ci-Cealkoxysulfonyl. Ci-Cehaloalkoxysulfonyl, cyano, nitre, phenyl, phenyl substituted by Ci-C4alkyl, Ci-C3haloaikyl, Ci-Caalkoxy, d-Cahaloalkoxy, cyano, nitro, halogen, Ci-Caalkylthio, Ci-Caalkylsulfinyl or Ci-Caalkylsulfonyl, or heteroaryl or heteroaryl substituted by Ct-C4alkyl, Ci-CahaloalkyI, Ci-Caalkoxy, Ci-Cahaioalkoxy, cyano, nitro, halogen, Ci-Caalkylthio, Ci-Caalkylsulfinyl or Ci-Csalkylsulfonyl; R' is hydrogen, Ci-CealkyI, Ci-CehaloalkyI, Ca-CycycloalkyI, Ci-Cealkoxy, Ci-Cehaloalkoxy, Ci-Cealkylsulfinyl, CrCealkylsulfonyl, Ci-Cealkylcarbonyl, Ci-Cehaloalkylcarbonyl, Cr Cealkoxycarbonyl, d-Cealkylaminocarbonyl, C2-C8dialkylaminocarbonyl, Ce-Cioarylsulfonyl, Ce-Cioarylcarbonyl, Ce-Cioarylaminocarbonyl, Cr-Ciearylalkylaminocarbonyl, Ci- Cgheteroarylsulfonyl, Ci-Cgheteroarylcarbonyl, Ci-Cgheteroarylaminocarbonyl, C2- Csheteroarylalkylaminocarbonyl; R" is hydrogen, Ci-CealkyI, Ci-CehaloalkyI, Ca-C/cycloalkyI, Ci-Cealkoxy, Ci-Cehaloalkoxy, Ci-Cealkylsuifinyl, CrCealkylsulfonyl, Ci-Cealkylcarbonyl, Ci-Cehaloalkylcarbonyl, Ci- Cealkoxycarbonyl, Ci-Cealkylaminocarbonyl, Ca-Cgdialkylaminocarbonyl, CrCehaloalkylsulfinyl or Ci-Cehaloalkylsulfonyr, nisO, 1,2. 3 or 4; and A denotes the position of attachment to the -(CR^R^)^,- moiety. -20- Groups Qi. Q2. Q3, Q4. Q5. Qe, Q?. Q25- Q26. Q27. Q28. Q29. Qse. Qa?. Qse. Qsg, Q90 are more preferred, and groups Qi to Q7 are particularly preferred. Preferably, R and R' are independently hydrogen, Ci-C4all-«' BA^' B W^ B Z B X B ^ Het, Hetj Hetg Het^ :ii- :^- :^-." >•• Hetg Hetg Het^ Hetg ^V^v_. "N^ "V^v ''N^ pio B '^ 1^10 B '^ Hetg Hetio Het„ Het,2 wherein: B designates the point of attachment to the ketoenol moiety; W' is N or CR^• W^ and W^ are Independently of each other N or CR^" W is N or CR'"; with the proviso that at least one of \N\ W^ W^ or W is N; X is O. S. or NR'^- Z is N or CR^^- wherein R^ is hydrogen, halogen, Ci-C4alkyl, Ci-C4haloalkyl, C2-C4alkenyl, C2-C4haloalkenyl, C2- C4alkynyl, Ci-C4alkoxy. Ci-C4haloalkoxy, Ci-C4alkylthio, Ci-C4alkylsulfinyl, Ci-C4alkylsulfonyl, nitro or cyano; preferably halogen, Ci-C2alkyl, Ci-Cahaloaikyl (e.g. CF3, CFjCI, CF2H, CCI2H, -22- FCH2, CICH2, BrCH2, CH3CHF, CF3CH2 or CHF2CH2). vinyl, ethynyl. or methoxy; and even more preferably methyl or ethyl; R' is hydrogen, d-Cealkyl, Ci-Cghaloalkyl (e.g. CF3, CF2CI, CF2H, CCI2H, FCH2, CICH2, BrCHz, CH3CHF. CF3CH2 or CHF2CH2), Ca-Cealkenyl. C2-C6haloalkenyl, C2-C6alkynyl, Cg-Ce cycloalkyi, Cs-Cecycloalkenyl, halogen, Ci-Cealkoxy, Ci-Cealkoxy-CrCealkyI, Ci- Cehaloalkoxy, optionally substituted aryl (e.g. optionally substituted phenyl), optionally substituted aryloxy (e.g. optionally substituted phenoxy), optionally substituted heteroaryl or optionally substituted heteroaryloxy; preferably optionally substituted aryl (e.g. optionally substituted phenyl) or optionally substituted heteroaryl v\/herein the optional substituents are selected from halogen. C1-C2 alkyl, C1-C2 alkoxy, C1-C2 haloalkyi (e.g. CF3, CF2CI, CF2H, CCI2H, FCH2, CICH2, BrCH2. CH3CHF, CF3CH2 or CHF2CH2), C,-C2 haloalkoxy, cyano or nitro; and even more preferably phenyl, substituted once, twice or three times, by halogen, C1-C2 alkyl, Ci-Cz alkoxy, C1-C2 haloalkyi (e.g. CF3, CF2CI, CF2H, CCI2H, FCH2. CICH2, BrCH2, CH3CHF. CF3CH2 or CHF2CH2), C1-C2 haloalkoxy or cyano; R® is hydrogen. C1-C4 alkyl, C2-C3alkenyl, C2-C3alkynyl, C1-C4 haloalkyi (e.g. CF3, CF2CI, CF2H. CCI2H. FCH2. CICH2. BrCHz. CH3CHF. CF3CH2 or CHF2CH2), or C2-C3 haloalkenyl; preferably methyl or ethyl; R^is hydrogen, methyl, halomethyl (e.g. CF3. CF2CI, CF2H, CCI2H, FCH2, CICH2, or BrCH2), or halogen; preferably hydrogen; R^° is hydrogen, halogen, Cj-C^ alkyl, C,-C4 haloalkyi (e.g. CF3, CF2CI. CFgH. CCI2H, FCH2, CICH2, BrCH2. CH3CHF. CF3CH2 or CHF2CH2), C2-C4alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, CrC4alkylth(o, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl or cyano; preferably hydrogen, halogen, methyl or ethyl; R" is hydrogen, methyl, ethyl, halomethyl (e.g. CF3, CF2CI, CF2H, CCI2H, FCH2, CICH2. or BrCHz), haloethyl (e.g. CH3CHF, CF3CH2 or CHF2CH2), optionally substituted aryl (e.g. optionally substituted phenyl) or optionally substituted heteroaryl; preferably optionally substituted aryl (e.g. optionally substituted phenyl) or optionally substituted heteroaryl wherein the optional substituents are selected from halogen, C1-C2 alkyl, C1-C2 alkoxy, C1-C2 haloalkyi (e.g. CF3, CF2CI, CF2H. CCI2H, FCH2. CICH2, BrCH2. CH3CHF, CF3CH2 or CHF2CH2), C1-C2 haloalkoxy, cyano or nitro; even more preferably phenyl, substituted once, twice or three times, by halogen, Ct-C2 alkyl, C1-C2 alkoxy, C,-C2 haloalkyi (e.g. CF3, CF2CI, CF2H, CCI2H, FCH2, CICH2, BrCH2, CH3CHF. CF3CH2 or CHF2CH2), C,-C2 haloalkoxy or cyano; R'^ is hydrogen, methyl, ethyl, or halomethyl (e.g. CF3, CF2CI, CF2H, CCI2H, FCH2, CICH2, or BrCHa); and -23- R^^ is hydrogen, methyl, ethyl, halomethyl (e.g. CF3, CF2CI, CF2H, CCI2H, FCH2, CICH2, or BrCH2), haloethyl (e.g. CH3CHF, CF3CH2 or CHF2CH2). halogen, cyano or nitro; preferably hydrogen. • More preferably. Het is a group of the formula Het2, wherein X is S and Z is N and R^ and R^ are as defined above. Preferably, in this embodiment, R^ is methyl or ethyl. Preferably, in this embodiment. R^ is phenyl, substituted once, twice or three times, by halogen, C1-C2 alkyl, C1-C2 alkoxy, C1-C2 haloalkyi, C1-C2 haloalkoxy or cyano; more preferably, R^ is phenyl substituted once, twice or three times (e.g. once) by halogen (e.g. chlorine); even more preferably. R^ is 4-chlorophenyl. It is also more preferred that Het is a group of the formula Hetio, wherein Z is CR^^ and R^, R^ and R^^ are as defined above. Preferably, in this embodiment, R^^ is hydrogen or methyl; more preferably hydrogen. Preferably, in this embodiment. R^ is methyl or ethyl. Preferably, in this embodiment. R^ is phenyl, substituted once, twice or three times, by halogen, C1-C2 alkyl, C1-C2 alkoxy, C1-C2 haloalkyi. C^-Cz haloalkoxy or cyano; more preferably, R^ is phenyl substituted once, twice or three times (e.g. once) by halogen (e.g. chlorine); even more preferably, R^ is 4-chlorophenyl. It is also preferred that Het is a group of the formula Het2, wherein X is S and Z is CR^^ and R^, R^ and R^^ are as defined above. Preferably, in this embodiment, R^^ is hydrogen. Preferably, in this embodiment. R® is methyl or ethyl. Preferably, in this embodiment, R^ is phenyl, substituted once, twice or three times, by halogen, C1-C2 alkyl, C1-C2 alkoxy, C1-C2 haloalkyi, C1-C2 haloalkoxy or cyano. It is also preferred that Het is a group of the formula Heti, wherein W' is CR®, W^ is N, W^ is CR^, W^ is N, and R^, R^ and R® are as defined above. Preferably, in this embodiment, R® is hydrogen. Preferably, in this embodiment, R® is methyl or ethyl. Preferably, in this embodiment, R' is phenyl, substituted once, twice or three times, by halogen. C1-C2 alkyl. Ci- C2 alkoxy, C1-C2 haloalkyi, C1-C2 haloalkoxy or cyano. In a group of preferred compounds of formula I, R^ is hydrogen or methyl; R^ and R^ independently are hydrogen or methyl; R" and R^ independently are hydrogen or methyl; and -24- Q is pyridyl. pyrimidinyl, pyridazinyl. quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl or quinoxalinyl, where these rings are optionally substituted one or two times by fluoro. chioro, bromo, methyl, methoxy. cyano or trifluoromethyl; or Q is thienyl, furyl, oxazoiyi, isoxazolyl, benzofuryl. thiazolyl, oxazolyl, isothiazolyl, benzothienyl, benzoisolhienyl, benzothiazolyl. benzisothiazolyl. benzoxazolyl or benzisoxazolyl, where these rings are optionally substituted one or two times by fluoro, chioro, bromo, methyl, methoxy, cyano or trifluoromethyl; and m is 1 ; Het is a group Hetj Het2 i wherein X is S, Z is N, R^ is methyl or ethyl, R^ is 4-chlorophenyl or 4-bromophenyl, and B designates the point of attachment to the ketoenol moiety; and G is hydrogen, an alkali metal or alkaline earth metal. Within this group of prefen'ed compounds of formula I, a particularly preferred group of compounds of formula I are those wherein R' to R® and G are hydrogen and Q, Het and m are as defined. In a particularly preferred group of the compounds of formula I, R^ to R^ are hydrogen and G is hydrogen, an alkali or alkaline earth metal, m is 1, Q is group selected from -.-^^ <-^' -.^^ -•-!>* --C^, Q, Q2 Q3 °* Q5 0. Q, -25- wherein n is 0 and A designates the point of attachment to the -{CR''R®)n, moiety, or Q is pyridyl, and Het is a group of the formula Hetg wherein X is S, Z is N, R^ is methyl or ethyl. R^ is phenyl substituted by halogen, and B designates the point of attachment to the ketoenol moiety, or Het is a group of the formula Hetio . wherein Z is CH or C-CH3. R^ is methyl or ethyl, R^ is phenyl substituted by halogen, and B designates the point of attachment to the ketoenol moiety. Even more preferably, Q is a group of the formula Q^ or pyridine-2-yl, and Het is a group of the formula Het2 or Hetio, wherein R^ is 4-chlorophenyl. In an alternative suitable embodiment. Het is a group of formula Heti3 : Heti3 , wherein: 8 designates the point of attachment to the ketoenol moiety; R*^ is halogen, Ci-Caalkyl. Ci-C2fluoroalkyl. vinyl, ethynyi, or methoxy; preferably methyl or ethyl; and R^^ is hydrogen or C,-C4alkyl. -26- Preferably, the compound of formula I is one of compounds A1 to A25 as shown below, or an agriculturally or agronomically acceptable salt thereof (e.g. agriculturally acceptable metal or ammonium salt, e.g. an alkali metal or alkaline earth metal salt thereof): I (Ai) CI'-'N^ (A2), °xr ^ n. c K \ ^ (A3), 8' (A4), ^ (A5), CI (A6), C' (A7), CI (A8), \=/ o 11 1 C" (A9). CI (A10), C'(A11), ci(A12), -27- F CI (A13), CI (A14)_ T p \ ° CI (A15), CI (A16). ^ ^ (A17), CI (A18), ^N^ _, p r ^ - ' N ^ /=\ J " I V^v Jl O (A19), ^ Cl(A20). F •^ ^ 0 ^^^^{A2n C (A22). o ^-^ ci(A23). ci(A24). o \^^Ci (A25). More preferably, the compound of formula I is one of compounds A7. A12, A16, A17, A18, A20, A23. A24 or A25 as shown above, or an agriculturally or agronomically acceptable salt -28- thereof (e.g. agriculturally acceptable metal or ammonium salt, e.g. an alkali metal or alkaline earth metal salt thereof). Certain compounds of formula (I) are alkenes, and as such undergo further reactions typical of alkenes to give additional compounds of formula (I) according to known procedures. Example of such reaction include, but are not restricted to, halogenation or hydrogenation ,OG 2 OG RI \ L RI \ X ^\f \--Z —" ^\f VX R^ R^ R' (I) (I) wherein R^ and R'' form a bond Compounds of formula (I) wherein R^ and R^ form a bond and R^ is halogen (preferably chloride or bromide) or R* is d-Cealkylsulfonate (preferably mesylate) or C,- Cehaloalkylsulfonate (preferably triflate) or an arylsulfonate (preferable tosylate) may undergo a cross-coupling reaction with a suitable coupling partner under conditions described in the literature for Suzuki-Miyaura, Sonogashira and related cross-coupling reactions to give additional compounds of formula (I) (see, for example, O'Brien, C. J. and Organ, M. G. Angew. Chem. Int. Ed. (2007), 46, 2768-2813; Suzuki, A. Journal of Organometallic Chemistry (2002), 653, 83; Miyaura N. and Suzuki. A. Chem. Rev. (1995), 95, 2457-2483). Those skilled in the art will appreciate that compounds of formula (I) may contain an heteroaromatic moiety bearing one or more substituents capable of being transformed into alternative substituents under known conditions, and that these compounds may themselves serve as intermediates in the preparation of additional compounds of formula (I). -29- Additional compounds of formula (I) may be prepared by selectively reducing compounds of formula (I) where Q is a Heteroaromatic ring prefereably furan or pyrrole in the presence of a suitable catalyst, and in a suitable solvent. R\ OG R\ OG 7^ \v Hydrogenalion I \> R^ ;,^ O R'k' ^ (I) (I) Q= Heteroaromatic Q= Heterocycle For example, compounds of formula (I) wherein R^, R^, R® or R^° is alkenyl or alkynyl, may be reduced to compounds of formula (I) wherein R®, R^. R® or R^° is alkyl under known conditions and compounds of formula (I) wherein R^ is halogen, preferably bromide or iodine, may undergo a cross-coupling reaction with a suitable coupling partner under conditions described in the literature for Suzuki-Miyaura, Sonogashira and related cross-coupling reactions to give additional compounds of formula (I) (see, for example, O'Brien, C. J. and Organ, M. G. Angew. Chem. Int. Ed. (2007), 46, 2768-2813; Suzuki. A. Journal of Organometallic Chemistry (2002), 653, 83; Miyaura N. and Suzuki, A. Chem. Rev. (1995), 95. 2457-2483). Compounds of formula (I) wherein G is Ci-CealkyI, C2-C8haloalkyl, phenylCi-Cgalkyl (wherein the phenyl may optionally be substituted by Ci-CaalkyI, Ci-Cahaloalkyl. Ci-Csalkoxy. Ci-Cahaloalkoxy, d-Caalkylthio, Ci-Caalkylsufinyl, Ci-Caalkyjsulfonyl, halogen, cyano or by nitro), heteroarylCi-Cgalkyl (wherein the heteroaryl may optionally be substituted by Ci- Csalkyl. Ci-CahaloaikyI, Ci-Caalkoxy, Ci-Cghaloalkoxy, Ci-Cgalkylthio, Ci-Caalkylsufinyl, d - Caalkylsulfonyl. halogen, cyano or by nitro). Ca-Ce alkenyl. Ca-Cahaloalkenyl, Ca-Csalkynyl, C(X^)-R', C(X'')-X'=-R^ C(X'')-N(R^)-R'*, -S02-R^ -P(X^)(RVR9 or CH2-X'-R*' where X^ X^ X'. X". X^, X'. R^ R^ R^ R", R^ R', R^ and R" are as defined above may be prepared by treating compounds of formula (A), which are compounds of formula (I) wherein G is H, with a reagent G-Z, wherein G-Z is alkylating agent such as an alkyl halide (the definition of alkyl halides includes simple Ci-Cs alkyl halides such as methyl iodide and ethyl iodide, substituted alkyl halides such as chloromethyl alkyl ethers, CI—CH2-X'-R^ wherein X* is oxygen, and chloromethyl alkyl sulfides CI—CH2-X'-R'', wherein X' is sulfur), a C-CaalkyI -30- sulfonate. or a di-Ci-CaalkyI sulfate, or with a Ca-Cealkenyl halide, or with a Ca-Cflall^ynyl halide. or with an acylating agent such as a carboxylic acid, HO-C(X^)R*, wherein X^ is oxygen, an acid chloride, CI-C(X^)R^, wherein X® is oxygen, or acid anhydride, [R^C(X^)]20, wherein X* is oxygen, or an isocyanate, R'=N=C=0, or a carbamoyl chloride, CI-C(X'')-N(R')- R^ (wherein X'^is oxygen and with the proviso that neither R'^ or R** is hydrogen), or a thiocarbamoyi chloride CI-C(X'')-N(R>R''(wherein X" is sulfur and with the proviso that neither R'' nor R"* is hydrogen) or a chloroformate, Cl-C{X^)-X''-R*', (wherein X** and X'' are oxygen), or a chlorothioformate CI-C(X'')-X''-R''(wherein X" is oxygen and X*' is sulfur), or a chiorodithioformate CI-C(X'*)-X''-R'', (wherein X" and X*^ are sulfur),oran isothiocyanate, R<=N=C=S. or by sequential treatment with carbon disulfide and an alkylating agent, or with a phosphorylating agent such as a phosphoryl chloride. CI-P(X*)(R')-R^ or with a sulfonylating agent such as a sulfonyl chloride CI-SO2—R®, preferably in the presence of at least one equivalent of base. Isomeric compounds of formula (I) may be formed. For example, compounds of formula (A) may give rise to two isomeric compounds of fonnula (I), or to isomeric mixtures of compounds of formula (I). This invention covers both isomeric compounds of formula (I), together with mixtures of these compounds in any ratio. O OG o 3 \ / > - H e t ^ 7 3 \ / % ^ H e t , \ / \ ^ H et yOm R1 0 Wm R1 O yOm R1 OG R' R' R' R' R' R* (A) (I) (I) The 0-alkylation of cyclic 1,3-diones is known; suitable methods are described, for example, in US4436666. Alternative procedures have t>een reported by Pizzorno, M. T. and Albonico, S. M. Chem. Ind. (London) (1972). 425; Born, H. ef a/. J. Chem. See. (1953). 1779; Constantino, M. G. et al. Synth. Commun. (1992), 22 (19), 2859; Tian, Y. et al. Synth. Commun. (1997). 27 (9), 1577; Chandra Roy, S. etal.. Chem. Lett. (2006), 35 (1), 16; Zubaidha, P. K. et al. Tetrahedron Lett. (2004), 45. 7187 and by Zwanenburg, B. et al. Tetrahedron (2005). 45 (22). 7109. - 3 1 - The acylation of cyclic 1,3-cliones may be effected by procedures similar to those described, for example, in US4551547, US4175135, US4422870, US4659372 and US4436666. Typically diones of formula (A) may be treated with the acylating agent in the presence of at least one equivalent of a suitable base, optionally in the presence of a suitable solvent. The base may be inorganic, such as an alkali metal carbonate or hydroxide, or a metal hydride, or an organic base such as a tertiary amine or metal alkoxide. Examples of suitable inorganic bases include sodium carbonate, sodium or potassium hydroxide, sodium hydride, and suitable organic bases include trialkylamines, such as trimethylamrne and triethylamine, pyridines or other amine bases such as 1,4-diazobicyclo[2.2.2]octane and 1,8- diazabicyclo[5.4.0]undec-7-ene. Preferred bases include triethylamine and pyridine. Suitable solvents for this reaction are selected to be compatible with the reagents and include ethers such as tetrahydrofuran and 1,2-dimethoxyethane and halogenated solvents such as dichloromethane and chloroform. Certain bases, such as pyridine and triethylamine, may be employed successfully as both base and solvent. For cases where the acylating agent is a carboxylic acid, acylation is preferably effected in the presence of a coupling agent such as 2-chloro-1-methylpyridinium iodide, W./V-dicyclohexylcarbodiimide, 1-(3- dimethylaminopropyi)-3-ethylcarbDdiimide and A/,/\/-carbodiimidazole, and optionally a base such as triethylamine or pyridine in a suitable solvent such as tetrahydrofuran, dichloromethane or acetonitrile. Suitable procedures are described, for example, by Zhang, W. and Pugh, G. Tetrahedron Lett. (1999), 40 (43), 7595 and Isobe, T. and Ishikawa, T. J. Org. Chem. (1999), 64 (19) 6984. Phosphorylation of cyclic-1,3-diones may be effected using a phosphoryl halide or thiophosphoryl halide and a base by procedures analogous to those described in US4409153. Sulfonylation of compounds of formula (A) may be achieved using an alkyl or aryl sulfonyl halide, preferably in the presence of at least one equivalent of base, for example by the procedure of Kowalski. C. J. and Fields, K. W. J. Org. Chem. (1981), 46, 197. Compounds of formula (A) may be prepared from a compounds of formula (I) by hydrolysis, preferably in the presence of an acid catalyst such as hydrochloric acid and optionally in the presence of a suitable solvent such as tetrahydrofuran or acetone preferably between 25 "C and 150 °C under conventional heating or under microwave irradiation. -32- OG O R ^ V S ^ ^ ^ * hydrolysis ^ ^-^\f^^^ yym R^ o "^^ (^1 o R' R' R= R^ (I) (A) In a further approach, compounds of formula (A) may be prepared by the cyclisation of a compound of formula (B) or a compound of formula (C), wherein R'" is hydrogen or an alkyl group, preferably in the presence of an acid or base, and optionally in the presence of a suitable solvent, by analogous methods to those described by T. N. Wheeler, US4209532. Compounds of formula (B) or compounds of formula (C) wherein R'" is hydrogen may be cyclised under acidic conditions, preferably in the presence of a strong acid such as sulfuric acid, polyphosphoric acid or Eaton's reagent, optionally in the presence of a suitable solvent such as acetic acid, toluene or dichloromethane. Het O R\ R' ( '^\ X^ M«t y R^ V = 0 cyclisation D3--V^ j^ Q / ~ - N R 3 ^ Q->^vA^ R"'0-A R2 yV"' R' ^ O R' R' (B) (A) OR'" O 1 V'R cyclisation Q S ^ ^ \ - - H et / \ ^ >—\ W"" R^ O R' R O Het R' R' (C) (A) Compounds of formula (B) or compounds of formula (C) wherein R'" is alkyl (preferably methyl or ethyl), may be cyclised under acidic or basic conditions, preferably in the presence of at least one equivalent of a strong base such as potassium fert-butoxide, lithium -33- diisopropylamide or sodium hydride and in a solvent sucli as tetrahydrofuran, toluene, dimethylsulfoxide or A/,A/-dimethylformamide. Compounds of formula (B) and compounds of formula (C), wherein R'" is H, may be esterified to, respectively, compounds of formula (B) and compounds of formula (C), wherein R'" is alkyl, under standard conditions, for example by heating with an alkyl alcohol, ROH, in the presence of an acid catalyst. Compounds of formula (B) and compounds of formula (C), wherein R'" is H, may be prepared, respectively, by saponification of a compounds of formula (D) and compounds of formula (E) wherein R"" is alkyl (preferably methyl or ethyl), under standard conditions, followed by acidification of the reaction mixture to effect decarboxylation, by similar processes to those described, for example, by T. N. Wheeler, US4209532. R'-'-O^C Het Hat R \ R ' \ R\R' ,( y. R' N—Q 1. saponification V R \ —Q ^ J r^R^ 2. decarboxylation ^ / r>R^ R - 0 - 4 R2 R-0-^ R2 O O (D) (B) OR"' OR"' 0 = ( 2 0=( 2 1 V^R 1. saponification 1 \r'^ Rv / x 3 '^^ /^ 3 Q N( R CO R"" Q-~.^ C>( ^ \hQ\ / ^ 2. decarboxylation vv^R R 0 Hal R' R 0 Het (E) (C) Compounds of formula (D) and compounds of formula (E), wherein R"" is alkyl, may be prepared by treating, respectively, compounds of formula (F) with suitable carboxylic acid chlorides of formula (G) or suitable carboxylic acid chlorides of formula (H) under basic conditions. Suitable bases include potassium /ert-butoxide, sodium bis(trimethylsilyl)amide and lithium diisopropylamlde and the reaction is preferably conducted in a suitable solvent (such as tetrahydrofuran or toluene) at a temperature of between -80 "C and 30 °C. Alternatively, compounds of formula (D) and compounds of formula (E), wherein R"" is H, may be prepared by treating a compound of formula (F) with a suitable base (such as -34- potassium (ert-butoxide, sodium bis(trimethylsilyl)amide and lithium diisopropylamide) in a suitable solvent (such as tetrahydrofuran or toluene) at a suitable temperature (between -80 °C and 30 °C) and reacting the resulting anion with a suitable anhydride of formula (J): OR'" / R1 R* N / R^ ^ ^ C l R-'OjC Het O R\ R' R""OX (°) >L R^ ) =0 Het , Q y—(C^ 3 3 D^ / R (F) "^X/^O O vf™ \ n R - R ^ / (D) (J) O R - 0 - ^ R 3 R RQI ORR- OJC 5^;*^ RI^ V '^ Rv /\ /^ ( (F) '^V/^^ '^^ ^'° ^^^ (J) Compounds of formula (F) are known compounds, or may be prepared from known compounds by known methods. Compounds of formula (J) may be prepared, for example, by analogous methods to those described by Ballini, R. et at. Synthesis (2002), (5), 681-685; Bergmeier, S. C. and Ismail, K. A. Synthesis (2000), (10). 1369-1371; Groutas, W. C. et al. J. Med. Chem. (1989), 32 (7). 1607-11 and Bernhard. K. and Lincke. H. Helv. Chim. Acta (1946), 29, 1457-1466. -35- Compounds of formula (G) or compounds of formula (H) may be prepared from a compound of formula (J) by treatment with an alkyl alcohol, R"'-OH, in the presence of a base, such as dimethylaminopyridine or an alkaline metal alkoxide (see, for example, Buser, S. and Vasella, A. Helv. Chim. Acta. (2005), 88, 3151 and M. Hart etal. Bioorg. Med. Chem. Letters, (2004), 14,1969), followed by treatment of the resulting acid with a chlorinating reagent such as oxalyl chloride or thionyl chloride under known conditions (see, for example, Santelli- Rouvier. C. Tetrahedron Lett. (1984). 25 (39). 4371; Walba D. and Wand, M. Tetrahedron Lett. (1982), 23 (48), 4995; Cason. J. Org. Synth. Coll. Vol. III. (169), 1955). ORRI P* a* R5 //° O V S ^ ° R"'-OH , V ^ Q Rl K 4 A V'O chlonnating agent ^JV R >vrO Ar—C\ R5/'4 / = " O C' (J) (G) (H) Compounds of fonnula (G) and compounds of formula (H) may be made from known compounds by known methods. For example, analogous methods to obtain compounds of fonnula (G) and compounds of formula (H) are described by Bergmeier, S. C. and Ismail, K. A. Synthesis (2000), (10). 1369-1371. In an further approach to compounds of formula (1) may be prepared by treating compounds of fonnula (K) with compounds of formula (L) wherein LG is a leaving group such as halogen (preferably Iodide, bromide or chloride) or an activated alcohol (preferably mesylate or tosylate) under basic conditions. Suitable bases include lithium diisopropylamide, sodium hexamethyldisilazide, potassium fert-butoxide and the reaction is preferably conducted in a suitable solvent (such as tetrahydrofuran) at a temperature between -80 "C and 30 °C GO R^ R^ 3 9^ / O ^„\^i o ^ R' R' (K) (1) -36- Compounds of formula (L) are kr^own, or may be made known compounds by known methods (see for example: WO2006016178; Ueno. H. et a/. J. Med. Chem. (2005), 48(10). 3586-3604; Kanoh, S. et al. Tetrahedron (2002), 58(35), 7049-7064; Strachan, J.-P. et al. J. Org. Chem. (2006). 71(26), 9909-9911). Compounds of fonnula (K) are known compounds or may be made from known compounds by known methods (see, for example. Song, Y. S. S. et al. Tetrahedron Lett. (2005), 46 (46), 5987-5990 and WO09030450) Alternatively, compounds of formula (K) wherein G is Ci-CealkyI may be prepared by alkylation of compounds of formula (K), wherein G is hydrogen under known conditions. Compounds of formula (K), wherein G is hydrogen, are known, or may be prepared from known compounds by known methods (see, for example, DE10118310). Alternatively, in a further approach to compounds of formula (K). compounds of formula (M), which are compounds of formula (K) wherein G is hydrogen and Het is (Heta) when R® is CH2R'"" and R'"" is hydrogen or methyl, may t»e prepared by thermal rearrangement of compounds of formula (AN), optionally in the presence of a suitable solvent and optionally under microwave irradiation. (N) (M) Preferably, the rearrangement is effected by heating compounds of formula (AN) at temperatures of between 120-300 °C, optionally in a suitable solvent such as 1,2- dimethoxyethane, diethylene glycol methyl ether, triglyme, tetraglyme. xylene, mesitylene or Dowtherm®, and optionally under microwave irradiation. Similarly, compounds of formula (O). which are compounds of formula (K) wherein G is hydrogen and Het is (Hets) when R^ is CH2R and R is hydrogen or methyl, may be prepared from compounds of formula (P) using similar methods. -37- Rttiii '^^^ r>-R^ — - iVf i O O (P) (O) Compounds of formula (N) may be prepared from compounds of formula (Q) by alkylation with compounds of formula (R), wherein L is a suitable leaving group such as a halogen or an alkyl- or aryl-sulfonate, optionally in the presence of a suitable base and optionally in a suitable solvent as described above for the alkylation of compounds of formula (A) R"'" \ \ ^ /A ^ R R Y^ base, solvent '^'^^^ O (Q) (N) Similarly, compounds of formula (P) may be prepared from compounds of formula (Q) by alkylation with compounds of formula (S), wherein L is a suitable leaving group such as a halogen or an alkyl- or aryl-sulfonate, under similar conditions. R p i / ^ base, solvent j-^y X O (Q) (P) -38- In an alternative approach, compounds of formula (N) may be prepared from compounds of formula (Q) by condensation with alcohols of formula (T), optionally in the presence of a suitable acid catalyst such as p-toluenesulfonic acid, or a Lewis acid catalyst, for example, ytterbium (III) trifluoromethanesulfonate, lanthanum (III) trifluoromethanesulfonate, sodium tetrachloroaurate (III) dihydrate, titanium (IV) chloride, indium (III) chloride or aluminium chloride, and optionally in a suitable solvent. Suitable solvents are selected to be compatible with the reagents used, and include, for example, toluene, ethanol or acetonilrile. Similar approaches have been described by. for example. M. Curini; F. Epifano. S. Genovese. Tetrahedron Lett. (2006), 47,4697-700; A. Arcadi, G. Bianchi, S. Di Giuseppe, F. Marinelli, Green Chemistry (2003), 5, 64-7. R"™ iL.£ R .J-V catalyst * ^ j ^ / V ^ - ^ R' ^ W solvent R'"'^^^ O (Q) (N) Alternatively, the condensation may be effected in the presence of suitable coupling agents such as 2-chloro-1-methylpyridinium iodide, N.N'-dicyclohexylcarbodiimide, 1.(3- dimethylaminopropyl)-3-ethylcarbodiimimde and N,N-carbodiimidazole and a suitable base such a triethylamine or pyridine in a suitable solvent such as tetrahydrofuran. acetonitrile or dichloromethane, or in the presence of a triarylphosphine (such as triphenylphosphine) and a dialkyi azidodicarboxylate (preferably diethyl azidodicarboxylate or diisopropyl azidodicarboxylate) and in a suitable solvent such as diethyl ether, tetrahydrofuran or 1,4- dioxane as described, for example, by O. Mitsunobu, Synthesis (1981), 1, 1-28. Using similar processes, compounds of formula (P) may be prepared by reaction of compounds of formula (Q) with compounds of formula (U). -39- R . / L V catalyst ' ' ^ " X / X ^ ' ^' R W solvent R^'^\O (Q) (P) Additional compounds of formula (N) wherein R^ is an aromatic or heteroaromatic moiety, or is an all-A 1—z—7— "-!> K^^ I y ^2 Sonogashira coupling y~-~^ ^ p i / " " ^ or similar R 'A O O (V) (N) For example, compounds of formula (V) may be treated with aryl-, heteroaryl-, alkyl-, alkenylor alkynylboronic acids, R^-B(0H)2, boronate esters. R^-B(0R""")2, wherein R is C,- Cealkyl or R^-B(OR""")2 represents cyclic boronate esters derived from a Ci-Cediol (especially preferred are cyclic boronate esters derived from pinacol), or a metal (especially potassium) aryl-, heteroaryl, alkyl-, alkenyl- and alkynyltrifluoroborate salts, M*[R^-BF3]" in the presence of a suitable palladium catalyst, a suitable ligand and a suitable base in the presence of a suitable solvent, under Suzuki-Miyaura conditions (see, for example K. Billingsley and S. Buchwald, J. Am. Chem. Soc. (2007), 129, 3358-3366; H. Stefani, R. Cella and A. Vieira, Tetrahedron (2007), 63, 3623-3658; N. Kudo, M. Perseghini and G. Fu, Angew. Chem. Int. Ed. (2006), 45, 1282-1284; A. Roglans, A. Pla-Quintana and M. Moreno- 40- Manas, Chem. Rev. (2006), 106, 4622-4643; J-H Li. Q-M Zhu and Y-X Xie. Tetrahedron (2006). 10888-10895; S. Nolan et al., J. Org. Chem. (2006). 71. 685-692; M. Lysen and K. Kdhler. Synthesis (2006), 4, 692-698; K. Anderson and S. Buchwald. Angew. Chem. Int. Ed. (2005), 44, 6173-6177; Y. Wang and D. Sauer, Org. Lett. (2004), 6 (16). 2793-2796; I. Kondolff, H. Doucet and M, Santelli. Tetrahedron. (2004), 60, 3813-3818; F. Bellina. A. Carpita and R. Rossi. Synthesis (2004), 15, 2419-2440; H. Stefani, G. Molander, C-S Yun, M. Ribagorda and B. Biolatto. J. Org. Chem. (2003), 68. 5534-5539; A. Suzuki. Journal of Organometallic Chemistry (2002), 653, 83; G. Molander and C-S Yun, Tetrahedron (2002), 58, 1465-1470; G. Zou. Y. K. Reddy and J. Faick, Tetrahedron Lett. (2001), 42, 4213-7215; S. Darses, G. Michaud and J-P, Genet, Eur. J. Org. Chem. (1999), 1877-1883). ,R R^-B(0H)2, R7-B(OR")2 R -L / Z catalyst, base, solvent JL / Z R ^ - ^ R^^ o b (V) (N) Alternatively, compounds of formula (N). wherein R^ is an optionally substituted acetylene, may be prepared from compounds of formula (V) by reacting with a terminal alkyne, R'-H, in the presence of a suitable palladium catalyst and optionally in the presence of a suitable copper co-catalyst, a suitable ligand, a suitable base and a suitable additive under conditions known to effect the Sonogashira coupling (see, for example, U. Sorenson and E Pombo- Villar, Tetrahedron (2005), 2697-2703; N. Leadbeater and B. Tominack, Tetrahedron Lett. (2003), 44. 8653-8656; K. Sonogashira, J. Organomet Chem. (2002). 653, 46-49). In a further approach, compounds of formula (N), wherein R^ is alkyl, optionally substituted vinyl, optionally substituted ethynyl, optionally substituted aryl or optionally substituted heteroaryl, may be prepared from compounds of formula (V) by reaction with a suitable organnostannane under Stille conditions (see, for example, R. Bedford, C. Cazin and S. Hazlewood (2002), 22, 2608-2609; S. Ley et al.. Chem. Commun. (2002). 10,1134-1135; G. Grasa and S. Nolan, Org. Lett. (2001). 3 (1), 119-122; T. Weskamp, V. Boehm. J. Organomet. Chem. (1999). 585 (2), 348-352; A. Littke and G. Fu. Angew. Chem. Int. Ed. (1999). 38 (16), 2411-2413; J. Stille et al.. Org. Synth. (1992), 71, 97). -41 - Compounds of formula (P) may be prepared from compounds of formula (W), wherein A and R'"" are as defined for compounds of formula (V), by analogous methods using appropriate starting materials. R R 2 o ^ \ Suzuki-Mlyaura coupling _2 o—R\ / \-Z Stiile coupling ,'^\ / V-Z y ^x Sonogashira coupling I, 7 ^x - i / ^ v ^ or related reactfon R'''^'^(( O O (W) (P) Compounds of fonnula (V) may be prepared from compounds of formula (Q), by reaction with compounds of formula (Z) wherein L is a suitable leaving group such as a halogen or an alkyl- or aryl-sulfonate, by processes analogous to those described above for the preparation of compounds of formula (N) from compounds of formula (Q). Alternatively, compounds of formula (V) may be prepared by reaction of compounds of formula (Q) with compounds of formula (AA) by processes analogous to those described above for the preparation of compounds of formula (N) from compounds of formula (Q). R (Z) base, solvent ' R"" (AA) catalyst, solvent -42- Compounds of formula (W) may be prepared from compounds of formula (Q), by reaction with compounds of formula (AB) wherein L is a suitable leaving group such as a halogen or an alkyl- or aryl-sulfonate, by processes analogous to those desaibed above for the preparation of compounds of fomiula (N) from compounds of formula (Q). Alternatively, compounds of formula (W) may be prepared by reaction of compounds of formula (Q) with compounds of formula (AB) by processes analogous to those described above for the preparation of compounds of fomiula (N) from compounds of formula (Q). R"'" (AB) base, solvent o ? o (AC) catalyst, solvent In an alternative approach, compounds of formula (Q) may be treated with a halogenating agent such as phosphorus oxychloride, phosphorus pentachloride, phosphorus pentabromide, phosphorus oxybromide, oxalyl chloride or oxalyl bromide, optionally in a suitable solvent such as toluene, chloroform, dichloromethane with optionally the presence of dimethylformamide, and the resulting vinyl halides of formula (AD), wherein Hal is chlorine or bromine may be converted by reaction with alcohols of formula (T), or of formula (U), or of formula (AA) or of formula (AC) optionally in the presence of a suitable base such as sodium hydride, sodium te/t-butoxide, potassium /ert-butoxide and a suitable solvent such as tetrahydrofuran, 1,4-dioxane. diethylene glycol dimethyl ether to give compounds of formula (N). formula (P), formula (V) and formula (W) respectively: -43- Z base, solvent / I ' :t^^'^"' DIMM \J X z '^) A^ ».>^,>>, ^d^' '"' •""•"^"' ATlry^, O O R O (Q) (AD) JL^X (P) R' 0 - \ _ (AA) base, solvent ^3 \ J F 'V (AC) base, solvent R\ / V-Z I :i^ t^ 0 (W) CompouncJs of formula (Q) are known compounds or may be made from known compounds by known methods. Those skilled in the art will appreciate that compounds of formula (K) may contain a heteroaromatic moiety bearing one or more substituents capable of being transformed into alternative substituents under known conditions, and that these compounds may themselves serve as intermediates in the preparation of additional compounds of formula (K). For example, a heterocycle of formula (M) wherein R' is alkenyl or alkynyl, may be reduced to compounds of formula (M) wherein R' is alky! under known conditions. -44- R\ ? ( Hj, catalyst f^\ / ( ^ , A ( ^ z A ^ . solvent ^}-~^z^^ o o wherein R26 is wherein R^^ is alkyl alky! or alkenyl In a further approach to compounds of formula (M), wherein Het is a group of formula (Het2), X is S. and Z is N, compounds of formula (AE) wherein L is a suitable leaving group such as a halogen or an alkyl- or haloalkylsulfonate, may be treated with compounds of formula (AF) in the presence of a suitable base (such as triethylamine or pyridine), and optionally in a suitable solvent (such as water, acetone, ethanol or isopropanol) according to known procedures, (see, for example, E. Knott, J. Chem. Soc. (1945), 455; H. Brederick, R. Gompper, Chem. Ber. (1960), 93, 723; B. Friedman, M. Sparks and R. Adams, J. Am. Chem. Soc. (1937), 59, 2262). S X R\ PH H,N R^ ^ OH R6 p i / ^ ^ V ^ V'R^ base, solvent ^ ^ ^ \ ^^^^R' 0 L O (AE) (K) where G is H and Het is Hetj X is S and Z is N Alternatively, compounds of formula (AE) may be treated with thiourea, by known procedures (see, for example, V. Pshenichniya, 0. Gulyakevich and V. Kripach, Chemistry of Heterocyclic Compounds (1990), 10,1409-1412), and the resulting products of formula (AG) may be converted into additional compounds of formula (K) by conversion to halides of formula (AH), wherein Hal is chlorine, bromine or iodine, under Sandmeyer conditions, and compounds of formula (AH) may be converted to compounds of formula (K) by crosscoupling under known conditions for the Suzuki-Miyaura, Sonogashira, Stille and related reactions, as described previously. - 4 5 - S R? P^^ A R? OH R^ R'^\^ /~^' base, solvent R ' ^ ^ N ^ N H O L 0 ^ (AE) (AG) Sandmeyer ^^~J\__j/^ cross-coupling R^—r^^^J^S 0 O (K) (AH) where G is H and Het is Hetj X is S and Z is N Compounds of formula (AE) may be prepared from compounds of formula (Q) under known conditions (see, for example, V. Pshenichniya, O. Gulyakevich and V. Kripach, Chemistry of Heterocyclic Compounds (1990). 10,1409-1412; V. Pshenichniya, O. Gulyakevich and V. Kripach. Russian Journal of Organic Chemistry (1989). 25 (9), 1882-1888). Compounds of fomiula (R), formula (S), formula (T), formula (U), formula (Z), formula (AA). formula (AB) and formula (AC) are known or may be prepared by known methods from known compounds (see, for example T. T. Denton. X. Zhang, J. R. Cashman, J. Med. Cham. (2005). 48, 224-239; J. Reinhard. W. E. Hull. C.-W. von der Lieth. U. Eichhorn, H.-C. Kliem. J. Med. Chem. (2001). 44. 4050-4061; H. Krausand H. Rege, DE19547076; M. L. Boys, L. A. Schretzman, N, S. Chandrakumar, M. B. Tollefson, S. B. Mohler, V. L. Downs, T. D. Penning, M. A. Russell, J. A. Wendt, B. B. Chen, H. G. Stenmark, H. Wu, D. P. Spangler. M. Clare, B. N. Desai, I. K. Khanna, M. N. Nguyen. T. Duffin, V. W. Engleman, M. B. Finn, S. K. Freeman, M. L. Hanneke. J. L. Keene. J. A. Klover, G. A. Nickols. M. A. Nickols, C. N. Steininger, M. Westlin, W. Westlin, Y. X. Yu, Y. Wang. C. R. Dalton. S. A. Norring. Bioorg. -46- Med. Chem. Lett. (2006), 16, 839-844; A. Silberg. A. Benko, G. Csavassy, Chem. Ber. (1964), 97,1684-1687; K. Brown and R. Newbury, Tetrahedron Lett. (1969), 2797; A. Jansen and M. Szeike, J. Chem. Soc. (1961), 405; R. Diaz-Cortes, A. Silva and L. Maldonado, Tetrahedron Lett. (1997), 38(13), 2007-2210; M. Friedrich, A. Waechtler and A De Meijure, Synlett. (2002), 4. 619-621; F. Kerdesky and L. Self. Synth. Commun. (1995), 25 (17). 2639- 2645; 2. Zhao, G. Scarlato and R. Armstrong., Tetrahedron Lett. (1991), 32 (13), 1609-1612; K-T. Kang and S. Jong, Synth. Commun. (1995), 25 (17), 2647-2653; M. Allamura and E. Perrotta. J. Org. Chem. (1993), 58 (1), 272-274). Alternatively, compounds of formula (I) where R^ and R" from a bond can be prepared from compounds of formula (AJ) by known methods (see for example Nagaoka, H. et al. Tetrahedron Letters (1985), 26 (41), 5053-5056; Nagaoka, H. etal. J. Am. Chem. Soc. (1986). 108 (16), 5019-5021; Zuki, M. etal. Bull. Chem. Soc. Japan (1988). 61(4), 1299- 1312; Enholm, E. J. ef al. J. Org. Chem. (1996). 61 (16). 5384-5390; Clive. D. L. J. et al. Tetrahedron (2001). 57 (18). 3845-3858; Bartoli. G. etal. J. Org. Chem. (2002), 67 (25), 9111-9114. Jung, M. E, etal. Chem. Comm. (2003). (2), 196-197; EP1433772; JP2004203844; INI94295) OG GQ R-V^^)—Het ''^ I R* OH Q-^ ""' R (AJ) (I) wherein R' and R* form a bond Compounds of formula (AJ) may be prepared by treating compounds of formula (K) with compounds of formula (AK) under basic conditions. Suitable bases include lithium diisopropylamide, sodium hexamethyldisilazide, potassium /ert-butoxide and the reaction is preferably conducted in a suitable solvent (such as tetrahydrofuran) at a temperature between -80 "C and 30 °C -47- O °>f^R' OG GO ^ ^ R\ 1 1 \ ^ /Het (AK) R?--y^^^Het R^ OH (•<) (AJ) Compounds of formula (AK) are known, or may be made from known compounds by known methods. Compounds of formula (I) (wherein G is Ci-C4alkyl) may be prepared by reacting a compounds of formula (AL) (wherein G is d-CAalkyl, and Hal is a halogen, preferably bromine or iodine), with heteroaryl boronic acids, Hel-B(0H)2 of fomiula (AM) or heteroaryl boronate esters in the presence of a suitable palladium catalyst (for example 0.001-50% palladium(ll) acetate with respect to compound (AL)) and a base (for example 1 to 10 equivalents potassium phosphate with respect to compound (AL)) and preferably in the presence of a suitable ligand (for example 0.001-50% (2-dicyclohexylphosphino)-2',6'- dimelhoxybiphenyl with respect to compound (AL)), and in a suitable solvent (for example toluene or 1.2-dimethoxyethane), preferably between 25 "C and 200 °C under conventional heating or under microwave irradiation (see, for example, Song, Y. S. S. et al. Tetrahedron Lett. (2005), 46 (46). 5987-5990). OG OG RI I R\ Jv 2 \ / % — H a l "Pd". ligand O O Y " ^ ^ " ®* R - ^ A / + (HO)2B-Het ,• R \ / Q^ A \ V base, solvent ^NvfW^^ yOm R^ O W™ R^ O R' R^ R' R' (AL) (AM) (I) Preferred coupling partners include heteroarylboronic acids, (Pi) to (P8),wherein R^ R^ R^, R^ R^°, R", X. W\ W^. W^ W and Z are as defined above. -48- HO.J>' "O^BA/^-"'-^BX'^"' "°^BA'^^' ' ' I OH OH OH OH ^" (AMi) (AM2) (AM3) (AM,) in °" ' in in (AM5) (AMe) (AM7) (AMg) Heteroarylboronic acids of formula (AM) are known compounds, or may be prepared from known compounds by known methods (see for example A. Voisin et al., Tetrahedron (2005), 1417-1421; A. Thompson et al, Tetrahedron (2005), 61, 5131-5135; K. Billingsley and S. Buchwald. J. Am. Chem. Soc. (2007), 129, 3358-3366; N. Kudo, M. Pauro and G. Fu. Angew. Chem. Int. Ed. (2006), 45.1282-1284; A. Ivachtchenkoef a/., J. Heterocyclic Chem. (2004), 41(6). 931-939; H. Matondo et al., Synth. Commun. (2003), 33 (5) 795-800; A. Bouillon etal.. Tetrahedron (2003), 59. 10043-10049; W. Li etal.. J. Org. Chem. (2002). 67, 5394-5397; C. Enguehard etal.. J. Org. Chem. (2000), 65. 6572-6575; H-N Nguyen, X. Huang and S. Buchwald, J. Am. Chem. Soc. (2003). 125.11818-11819, and references therein). Compounds of formula (AL) may be prepared by halogenating compounds of formula (AN), followed by alkylation of the resulting halide of formula (AO) with a CrC4alkyl halide or tri-Ci-C4alkylorthoformate under known conditions, for example by the procedures of Shepherd R. G. et al. J. Chem. Soc. Perkin Trans. 1 (1987), 2153-2155 and Lin Y. -L. et al. Bioorg. Med. Chem. (2002), 10, 685-690. Alternatively, compounds of formula (AL) may be prepared by alkylating a compound of formula (AN) with a Ci_4alkyl halide or a tri-Ci^- alkylorthoformate, and halogenating the resulting enone of formula (AP) under known conditions (see for example Song, Y. S. et al. Tetrahedron Lett. (2005), 46 (36), 5987-5990; Kuethe, J. T. etal. J. Org. Chem. (2002), 67(17), 5993-6000; Belmont, D. T. et al. J. Org. Chem. 1985. 50 (21), 4102-4107). -49- R\ /? halogenation j ^ /~~Hal y\ R'0 alkylation R^R^ ° R^k ° (AN) (AL) ,R\ P^ alkylation '^ iTx^ halogenation (AP) Compounds of formula (AP) may be prepared by treating compounds of formula (AQ) with compounds of formula (L) wherein LG is a leaving group such as halogen (preferably iodide or bromide) or an activated alcohol (preferably mesylate or tosylate) under basic conditions. Suitable bases include lithium diisopropylamide, sodium hexamethykJisilazide, potassium /erf-butoxide and the reaction is preferably conducted in a suitable solvent (such as tetrahydrofuran) at a temperature between -80 "C and 30 °C (see, for example, Gulias, M. et al. Org. Lett. (2003), 5(11). 1975-1977; Altenbach. R. J. et a/. J. Med. Chem. (2006), 49 (23), 6869-6887; Snowden, R. L. Tetrahedron (1986), 42 (12), 3277-90; Oppolzer, W. et al. Helv. Chim. Acta (1980), 63 (4), 788-92; Mellor, M. et al. Synth. Commun. 1979. 9 (1), 1-4). Q.^LG / o W"'R'R' R' R* ° (AQ) (AP) -50- Compounds of formula (AQ) are known, or may be made from known compounds by known methods. Alternatively compounds of formula (AP) where R^ and R* from a bond can be prepared from compounds of formula (AR) by known methods (see, for example, Nagaoka, H. et al. Tetrahedron Letters (1985). 26 (41). 5053-5056; Nagaoka, H. et al. J. Am. Chem. Soc. (1986). 108 (16). 5019-5021; zuki. M. etal. Bull. Chem. Soc. Japan (1988). 61(4). 1299- 1312; Enholm. E. J. etal. J. Org. Chem. (1996), 61 (16). 5384-5390; Clive. D. L. J. etal. Tetrahedron (2001). 57 (18). 3845-3858; Bartoli. G. etal. J. Org. Chem. (2002). 67 (25), 9111-9114. Jung. M. E. et al. Chem. Comm. (2003), (2), 196-197; EP1433772; JP2004203844; IN 194295). OG '^>£^/M. " R'^\Q'TliST-/ o D« R^ It O R OH U^ , Q ^ (AR) (AP) wherein R' and R* form a bond Compounds of fonnula (AR) may be prepared by treating compounds of formula (AQ where in R^ is hydrogen) with compounds of formula (AK) under basic conditions. Suitable bases include lithium diisopropylamide. sodium hexamethyldisilazide. potassium (ert-butoxide and the reaction is preferably conducted in a suitable (such as tetrahydrofuran) at a temperature between -80 °C and 30 "C (see, for example. Aleman, J. et al. Chem. Comm. (2007), (38), 3921-3923). O GO H H 3 j O Q-\ )mT^ 0 R^ OH (AQ) (AR) wherein R^ is hydrogen -51 - Compounds of formula (AN) may be prepared from compounds of formula (AP) by hydrolysis, preferably in the presence of an acid catalyst such as hydrochloric acid and optionally in the presence of a suitable solvent such as tetrahydrofuran or acetone preferably between 25 °C and 150 °C under conventional heating or under microwave irradiation. / hydrolysis ^ R* R^ R' R (AP) (AN) Alternatively, compounds of formula (AN) can be made from known compounds by known methods (see for example Manukina, T. A. et al. Zhurnal Organicheskoi Khimii (1986), 22(4), 873-4; Mellor, M. et al. Synth. Commun. 1979. 9 (1), 1-4). In a further approach, compounds of formula (A) may be prepared by reacting compounds of formula (AN) with suitable heteroaryl halides (Het-Hal where Hal is, for example, an iodide or bromide), in the presence of a suitable palladium catalyst (for example 0.001-50% palladium(ll) acetate with respect to compound (AN)) and a base (for example 1 to 10 equivalents potassium phosphate with respect to compound (AN)) and preferably in the presence of a suitable ligand (for example 0.001-50% (2-dicyclohexylphosphino)-2',4',6'- triisopropylbiphenyl with respect to compound (AN)), and in a suitable solvent (for example 1,4-dioxane), preferably between 25°C and 200°C. Similar couplings are known in the literature (see for example, J. M. Fox, X. Huang, A. Chieffi, and S. L. Buchwald, J. Am. Chem. Soc. (2000), 122, 1360-1370; B. Hong etal. WO 2005/000233). Alternatively, compounds of formula (A) may be prepared by reacting compounds of formula (AN) with suitable heteroaryl halides (Het-Hal where Hal is. for example, an iodide or bromide) in the presence of a suitable copper catalyst (for example 0.001-50% copper(l) iodide with respect to compound (AN)) and a base (for example 1 to 10 equivalents potassium carbonate with respect to compound (AN)) and preferably in the presence of a suitable ligand (for example 0.001-50% L-proline with respect to compound (AN)), and in a suitable solvent (for example dimethylsulfoxide), preferably between 25°C and 200°C. Similar - 5 2 - couplings are known in the literature for aryl halides (see for example, Y. Jiang, N. Wu, H. Wu, and M. He. Synlett (2005). 18,2731-2734). R? O ^R^y P ^ J ' x catalyst, ligand | ^Q / L / + Het-Hal " Q..,^^A-^^/^^^ OOm * i\\ base, solvent (AN) (A) In a further approach, compounds of fonnuia (A) may be prepared by reaction of compounds of formula (AN) with a heteroaryl lead tricarboxylates under conditions described in the literature (for example see, J. T. Pinhey, B. A. Rowe, Aust. J. Chem. (1979), 32, 1561-6; J. Morgan, J. T. Pinhey, J. Chem. Soc. Perkin Trans. 1 (1990), 3, 715-20; J. T. Pinhey, Roche, E. G. J. Chem. Soc. Perkin Trans. 1 (1988), 2415-21). Preferably the heteroaryl lead tricarboxylates are heteroaryl triacetates of formula (AS) and the reaction is conducted in the presence of a suitable ligand (for example N,N-dimethylaminopyridine, pyridine, imidazole, bipyridine, and 1,10-phenanthroline, preferably one to ten equivalents of N,Ndimethylaminopyridine with respect to compound (AN)) and in a suitable solvent (for example chloroform, dichloromethane and toluene, preferably chloroform and optionally in the presence of a co-solvent such as toluene) at 25°C to lOO'C (preferably 60-90°C). R\ P R3 P / \ 1 ligand, solvent / Q Jr^/ + AcO—Pb—Het ^ Q J \ / ^ H et Y-^h^ OAc 25oCto100oC y f \^ (AN) (AS) (A) Compounds of formula (AS) may be prepared from compounds of formula (AM) by treatment with lead tetraacetate in a suitable solvent (for example chloroform) at 25°C to 100°C (preferably 25-50°C), optionally in the presence of a catalyst such as mercury diacetate, according to procedures described in the literature (for example see, K. Shimi, G. Boyer, J-P. Finet and J-P. Galy, Letters in Organic Chemistry (2005), 2, 407-409; J. Morgan and J. T. Pinhey, J. Chem. Soc. Perkin Trans. 1 (1990), 3, 715-20). -53- HO 9^^ \ Pb(OAc)4 1 B-Het ~ ^ AcO—Pb—Het / I HO Hg(0Ac)2, solvent OAc (AM) (AS) Additional compounds of formula (A) may be prepared by reacting an iodonium ylide of formula (AT), wherein Ar is an optionally substituted phenyl group, and an aryl boronic acid of formula (AM), in the presence of a suitable palladium catalyst, a base and in a suitable solvent. R\ /? R^ P l \ ^ ^^\ catalyst, base 1—Q l^y^''='-~Ar + ^B-Het .- Q i. / ^ H et yT^ki\\ HO additive, solvent ^W^MXC R'^ R^ ° R^ J,^ '^ O (AT) (AM) (A) Suitable palladium catalysts are generally palladium(ll) or palladium(O) complexes, for example palladium(l!) dihalides, palladium(li) acetate, palladium(ll) sulfate, bis(triphenylphosphine)-palladium(ll)dichloride, bis(tricyclopentylphosphine)palladium(ll) dichloride, bis(tricyclohexyl-phosphine)palladium(ll)dichloride, bis(dibenzylideneacetone)palladium(0) or tetrakis-(triphenylphosphine)palladium(0). The palladium catalyst can also be prepared in situ from palladium(ll) or palladium(O) compounds by complexing with the desired ligands, by, for example, combining the palladium(ll) salt to be complexed, for example palladium(ll) dichloride (PdCl2) or palladium(ll) acetate (Pd(0Ac)2), together with the desired ligand, for example triphenylphosphine (PPhs), tricyclopentylphosphine. tricyclohexylphosphine, 2-dicyciohexylphosphino-2',6'- dimethoxybiphenyl or 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl and the selected solvent, with a compound of formula (AT), the arylboronic acid of formula (AM), and a base. Also suitable are bidendate ligands, for example 1,1'-bis(diphenylphosphino)ferrocene or 1,2-bis(diphenylphosphino)ethane. By heating the reaction medium, the palladium(ll) complex or palladium(O) complex desired for the C-C coupling reaction is thus formed in situ, and then initiates the C-C coupling reaction. The palladium catalysts are used in an amount of from 0.001 to 50 mo! %, preferably in an amount of from 0.1 to 15 mol %, based on the compound of formula (AT). The reaction may -54- also be carried out in the presence of other additives, such as tetralkylammonium salts, for example, tetrabutylammonium bromide. Preferably the palladium catalyst is palladium acetate, the base is lithium hydroxide and the solvent is aqueous 1,2-dimethoxyethane. A compound of formula (AT) may be prepared from a compound of formula (AN) by treatment with a hypervalent iodine reagent such as a (diacetoxy)iodobenzene or an iodosylbenzene and a base such as aqueous sodium carbonate, lithium hydroxide or sodium hydroxide in a solvent such as water or an aqueous alcohol such as aqueous ethanol according to the procedures of Schank K. ef al. Synthesis (1983), 392, Moriarty R.M.et al. J. Am. Chem. Soc. (1985). 107, 1375 or of Yang Z. et al. Org. Lett. (2002). 4 (19), 3333. l \ Arl(OAc)2 or ArlO, base j \. R* R^ O R'k ^ (AN) (AT) In a further approach to compounds of fonriula (A), compounds of fonmula (AU), which are compounds of formula (I) wherein G is hydrogen and Het is (Heta) when R® is CH2R and R is hydrogen or methyl, may be prepared by thermal rearrangement of compounds of formula (AU). optionally in the presence of a suitable solvent and optionally under microwave irradiation. r. A-^/ ^ solvent Q-+vi\\\ Z^'^D^ R^R^ O R R (AV) (AU) Preferably, the rearrangement is effected by heating compounds of formula (AT) at temperatures of between 120-300 "C, optionally in a suitable solvent such as 1,2- dimethoxyethane, diethylene glycol methyl ether, triglyme, tetraglyme, xylene, mesitylene or Dowtherm®, and optionally under microwave irradiation. -55- Similarly, compounds of formula (AW), which are compounds of formula (I) wherein G is hydrogen and Het is (Heta) when R® is CH2R and R is hydrogen or methyl, may be prepared from compounds of formula (AX) using similar methods. pMMI R*"*' «'-vv r>-R' —- „ x y ^ i ] / X solvent Q-YVTV^ X-'^D? R^ R (AX) (AW) Compounds of formula (AV) may be prepared from compounds of formula (AN) by alkylation with compounds of fonnula (R). wherein L is a suitable leaving group such as a halogen or an alkyl- or aryl-sulfonate. optionally in the presence of a suitable base and optionally in a suitable solvent as described above for the alkylation of compounds of formula (A) R T ^^' R R\ P ^ Ji oAV ^ ^~T> S^«^ "Wm^jiW base, solvent Q^y\~~~r( R' R j\,^ o R^ R' (AN) (AT) Similarly, compounds of formula (AX) may be prepared from compounds of formula (AN) by alkylation with compounds of formula (S), wherein L is a suitable leaving group such as a halogen or an alkyl- or aryl-sulfonate, under similar conditions. -56- R Q - M A ^ base, solvent L 7 X R' R I\,^ O R* R (AN) (AX) In an alternative approach, compounds of formula (AV) may be prepared from compounds of formula (AN) by condensation with alcohols of formula (T), optionally in the presence of a suitable acid catalyst such as p-toluenesulfonic acid, or a Lewis acid catalyst, for example, ytterbium (III) trifluoromethanesulfonate, lanthanum (III) trifluoromethanesulfonate, sodium tetrachloroaurate (III) dihydrate, titanium (IV) chloride, indium (III) chloride or aluminium chloride, and optionally in a suitable solvent. Suitable solvents are selected to be compatible with the reagents used, and include, for example, toluene, ethanol or acetonitrile. Similar approaches have been described by, for example, M. Curini, F. Epifano, S. Genovese, Tetrahedron Lett. (2006), 47, 4697-700; A. Arcadi. G. Bianchi, S. Di Giuseppe. F. Marinelli, Green Chemistry (2003), 5,64-7. R WmrjAv solvent ^tifl^iV^ R R R' R' ° (AN) (AV) Alternatively, the condensation may be effected in the presence of suitable coupling agents such as 2-chloro-1-methylpyridinium iodide, N.N'-dicyclohexylcarbodiimide. 1,(3- dimethylaminopropyl)-3-ethylcarbodiimimde and N,N-carbodiimidazole and a suitable base such a triethylamine or pyridine in a suitable solvent such as tetrahydrofuran, acetonitrile or -57- dichloromethane, or in the presence of a triarylphosphine (such as triphenylphosphine) and a dialkyi azidodicarboxylate (preferably diethyl azidodicarboxylate or diisopropyl azidodicarboxylate) and in a suitable solvent such as diethyl ether, tetrahydrofuran or 1,4- dioxane as described, for example, by O. Mitsunobu, Synthesis (1981), 1.1-28. Using similar processes, compounds of formula (AX) may be prepared by reaction of compounds of formula (AN) with compounds of formula (U). R'"" 1 > ^~l\ ^ /^R' Q-Yv^A^ catalyst i / X ^ " . RA\ solvent ° ^ ( x C^ R^R^ ° /,.^0 (AN) (AX) Additional compounds of formula (AV) w/herein R'' is an aromatic or heteroaromatic moiety, or is an alkyl, alkenyl or alkynyl group, may be prepared by the reaction of compounds of formula (AY), wherein A is an atom or group suitable for undergoing cross-coupling reactions (for example A is chlorine, bromine or iodine, or a haloalkylsulfonate such as trifluoromethanesulfonate), and R'"" is as defined for compound of formula (O), with a suitable coupling partner under conditions described in the literature for Suzuki-Miyaura. Sonogashira, Stille and related cross-coupling reactions. p2 P ^ X ^ Y Suzuki-Miyaura coupling p2 P ' N V ^Y 3 \ ^ if \ Stille coupling a \ ^ n \ ^ " T \ ^.^A — — — - ^-ys ^,-^R^ Q JU-y Sonogashira coupling Q . / W ^ ^fxIrnVTiu or similar ^txli^Vju R^R^ ° R^R^ ° (AY) (AV) -58- For example, compounds of fomiula (AY) may be treated with aryl-. heteroaryl-, alkyl-, alkenyl- or aikynylboronic acids. R^-B(0H)2, boronate esters. R'-B(0R""")2, wtierein R""" is Ci-CealkyI or R^-B{OR )2 represents cyclic boronate esters derived from a Ci-Cediol (especially preferred are cyclic boronate esters derived from pinacol). or a metal (especially potassium) aryl-, heteroaryl, alkyl-, alkenyl- and alkynyltrifluoroborate salts, M*[R^-BF3]' in the presence of a suitable palladium catalyst, a suitable ligand and a suitable base in the presence of a suitable solvent, under Suzuki-Mlyaura conditions (see, for example K. Billingsley and S. Buchwald, J. Am. Chem. Soc. (2007), 129. 3358-3366; H. Stefani, R. Cella and A. Vieira, Tetrahedron (2007), 63, 3623-3658; N. Kudo. M. Perseghini and G. Fu, Angew. Chem. Int. Ed. (2006), 45,1282-1284; A. Roglans, A. Pla-Quintana and M. Moreno- Manas, Chem. Rev. (2006), 106, 4622-4643; J-H Li, Q-M Zhu and Y-X Xie, Tetrahedron (2006). 10888-10895; S. Nolan et al.. J. Org. Chem. (2006), 71, 685-692; M. Lysen and K. Kohler, Synthesis (2006), 4, 692-698; K. Anderson and S. Buchwald. Angew. Chem. Int. Ed. (2005). 44. 6173-6177; Y. Wang and D. Sauer, Org. Lett. (2004), 6 (16). 2793-2796; I. Kondolff. H. Doucet and M. Santelli, Tetrahedron, (2004), 60, 3813-3818; F. Bellina, A. Carpita and R. Rossi, Synthesis (2004), 15, 2419-2440; H. Stefani, G. Molander, C-S Yun, M. Ribagorda and B. Biolatto, J. Org. Chem. (2003), 68. 5534-5539; A. Suzuki, Journal of Organometallic Chemistry (2002), 653. 83; G. Molander and C-S Yun. Tetrahedron (2002), 58,1465-1470; G. Zou. Y. K. Reddy and J. Falck. Tetrahedron Lett (2001). 42, 4213-7215; S. Darses. G. Michaud and J-P, Genet. Eur. J. Org. Chem. (1999), 1877-1883). r R7-B(OH)2, R^-B(OR")2 / f\^ ir\ orMIR^BFJ- j \ ^ /T^ Q y\~^ ^ catalyst, base, solvent Q ^/A~~-y^ ^ R^R* ° R^R^ ° (AY) (AV) Alternatively, compounds of formula (AV), wherein R' is an optionally substituted acetylene, may be prepared from compounds of formula (AY) by reacting with a terminal alkyne. R^-H. in the presence of a suitable palladium catalyst and optionally in the presence of a suitable copper co-catalyst, a suitable ligand, a suitable base and a suitable additive under conditions known to effect the Sonogashira coupling (see, for example, U. Sorenson and E Pombo- 59- Villar, Tetrahedron (2005), 2697-2703; N. Leadbeater and B. Tominack. Tetrahedron Lett. (2003), 44, 8653-8656; K. Sonogashira, J. Organomet. Chem. (2002), 653, 46-49). In a further approach, compounds of formula (AV). wherein R^ is alkyl, optionally substituted vinyl, optionally substituted ethynyl, optionally substituted aryl or optionally substituted heteroaryl, may be prepared from compounds of formula (AY) by reaction with a suitable organnostannane under Stille conditions (see, for example, R. Bedford, C. Cazin and S. Hazlewood (2002). 22. 2608-2609; S. Ley e^ a/.. Chem. Commun. (2002). 10,1134-1135; G. Grasa and S. Nolan, Org. Lett. (2001). 3 (1), 119-122; T. Weskamp, V. Boehm, J. Organomet. Chem. (1999), 585 (2). 348-352; A. Littke and G. Fu. Angew. Chem. Int. Ed. (1999). 38 (16), 2411-2413; J. Stille et al.. Org. Synth. (1992), 71. 97). Compounds of formula (AX) may be prepared from compounds of formula (AZ), wherein A and R'"" are as defined for compounds of formula (AY), by analogous methods using appropriate starting materials. p2 P^'\^y Suzuki-Miyaura coupling „2 0~\^ Q / U ^ / ^ Sonogashira coupling ^ >A^^/ ^ "h^fm p i ^ or related reaction VT^m^Vi R4^ ° R4^ ' ° (AX) (AX) Compounds of formula (AY) may be prepared from compounds of formula (AN), by reaction with compounds of formula (Z) wherein L is a suitable leaving group such as a halogen or an alkyl- or aryl-sulfonate. by processes analogous to those described above for the preparation of compounds of formula (AV) from compounds of formula (AN). Alternatively, compounds of formula (AY) may be prepared by reaction of compounds of formula (AN) with compounds of formula (AA) by processes analogous to those described above for the preparation of compounds of formula (AV) from compounds of formula (AN). -60- R (Z) base, solvent (AN) H 0 ^ \ ;, R^R^ ° ^ Z (AV) (AA) catalyst, solvent Compounds of formula (AZ) may be prepared from compounds of formula (AN), by reaction with compounds of formula (AB) wherein L is a suitable leaving group such as a halogen or an alkyl- or aryl-sulfonate, by processes analogous to those described above for the preparation of compounds of formula (AV) from compounds of formula (AN). Alternatively, compounds of formula (AZ) may be prepared by reaction of compounds of formula (AN) with compounds of formula (AB) by processes analogous to those described above for the preparation of compounds of formula (AV) from compounds of formula (AN). - 6 1 - R (AB) base, solvent (AN) HO"\j-\^A ^'^* ° ^ X I (A2) (AC) catalyst, solvent In an alternative approach, compounds of formula (AN) may be treated with a halogenating agent such as phosphorus oxychloride, phosphorus pentachloride, phosphorus pentabromide, phosphorus oxybromide, oxalyl chloride or oxalyl bromide, optionally in a suitable solvent such as toluene, chloroform, dichloromethane with optionally the presence of dimethylformamide, and the resulting vinyl halides of formula (BA), w/herein Hal is chlorine or bromine may be converted by reaction with alcohols of formula (T), or of fonnula (U), or of fonnuia (AA) or of formula (AC) optionally in the presence of a suitable base such as sodium hydride, sodium fe/t-butoxide, potassium tert-butoxide and a suitable solvent such as tetrahydrofuran, 1,4-dioxane, diethylene glycol dimethyl ether to give compounds of formula (AV), formula (AX), formula (AY) and formula (AZ) respectively: -62- R Z base, solvent j (T) R! P'V-X I «'-H C>-R' R-" R' R* ° R\ /? R\ ? R? o - ^ , R ' - V A U . . R'—\--^ <^> "^se, solvent ,'^\ / V-? vr R & W" R o w- R^ R'R' ° R'R^ ° R-" P4* O I X " ^ (AX) (M) base, solvent _3 \ ^ y 'iL.c.\ base, solvent R\ / \—2 I—^^2! . R O A rv-A R'R^ ° (AZ) Compounds of formula (BA) may be also prepared from compounds of formula (BB) by an intramolecular FrIedel-Crafts-type cyclisation by treating the carboxylic acid (BB) with halogenating agent, such as phosphorus oxychloride, phosphorus pentachloride, phosphorus pentabromide, phosphorus oxybromide, oxalyl chloride or oxalyl bromide, optionally in a suitable solvent such as toluene, chloroform, dichloromethane with optionally the presence of dimethylformamide, treating the reaction mixture with a Lewis acid, preferably AICI3 and subsequently doing a standard aqueous workup, using, for example, a saturated aqueous solution of sodium bicarbonate (see, for example, Y. Xu ei al. J. Org. Chem. 2009, DOI: 10.1021/jo900696k). -63- I^OH ^ XV A' ° R4' ° (^« (BA) Compounds of formula (BB) may be prepared from compounds of formula (BC), by reaction 2-chloro-3-iodopropene derivates under basic conditions. Suitable bases include sodium bis(trimethylsilyl)amide, lithium diisopropylamide, n-butyl lithium and the reaction is preferably conducted in a suitable solvent (such as tetrahydrofuran or toluene) at a temperature of between -80 °C and 30 "C (see, for example, Y. Xu e^ al. J. Org. Chem. 2009, DOI: 10.1021/jo900696k). 2 9' Q X^^^ ° 1 5'* 4 ^ 0 R*R (BC) (BB) Compounds of formula (BC) are known or may be made from known compounds by known methods. In a further approach to compounds of formula (A), wherein Het is a group of formula (Hetz), X is S, and 2 is N, compounds of formula (BD) wherein L is a suitable leaving group such as a halogen or an alkyl- or haloalkylsulfonate, may be treated with compounds of formula (BE) in the presence of a suitable base (such as triethylamine or pyridine), and optionally in a suitable solvent (such as water, acetone, ethanol or isopropanol) according to known procedures, (see, for example, E. Knott, J. Chem. Soc. (1945), 455; H. Brederick, R. Gompper, Chem. Ber. (1960), 93, 723; B. Friedman, M. Sparks and R. Adams, J. Am. Chem. Soc. (1937), 59. 2262). -64- S p2 OH H^N R' PJ2 OH p6 ^^ Z' »- y — ^ I Q-fr^t'A^^ ^—R® base, solvent ^^(W\^ N^^o' Wm R1\\ / ^A''" R ^^ '^ R 4 ' ° ' R4^ ° (BD) (K) where G is H and Het is Het2 X is S and Z is N Alternatively, compounds of formula (BD) may be treated with thiourea, by known procedures (see, for example, V. Pshenichniya, O. Gulyakevich and V. Kripach, Chemistry of Heterocyclic Compounds (1990), 10,1409-1412), and the resulting products of formula (BF) may be converted into additional compounds of formula (I) by conversion to halides of formula (BG), wherein Hal is chlorine, bromine or iodine, under Sandmeyer conditions, and compounds of formula (BG) may be converted to compounds of fomiula (I) by cross-coupling under known conditions for the Suzuki-Miyaura, Sonogashira, Stille and related reactions, as described previously. -65- R^ P X R\ n R^ V ' D i T - R ' base, solvent " " ^ ^ ''" NH, (BD) (Bf^) Sandmeyer R?—V--A, / / " S cross-coupling R—\ \ _ _ _ / /^ R4^ ° R^R^ ° (I) (B6) where G is H and Het is Het2 X is S and Z is N Compounds of formula (BD) may be prepared from compounds of formula (AN) under known conditions (see, for example. V. Pshenichniya, O. Gulyakevich and V. Kripach, Chemistry of Heterocyclic Compounds (1990), 10,1409-1412; V. Pshenichniya. O. Gulyakevich and V. Kripach. Russian Journal of Organic Chemistry (1989), 25 (9), 1882-1888). Additional compounds of formula (A) may be prepared by the pinacol rearrangement of compounds of formula (BG) or compounds of formula (BJ) wherein R ' is C1-C4 alkyl (preferably methyl) under acidic conditions (see, for example, Eberhardt, U. et al. Chem. Ber. (1983). 116(1). 119-35 and Wheeler, T. N. US4283348) -66- ^ OSi(R )3 , OH 9\ OH R\ R^ O pSi(R )3 JXA j^2y\iL-R Het "^ R^^^y/ \ rearrangement ^"XX)\~^ R^ R* (BH) (BJ) (A) Compounds of formula (BH) and compounds of formula (BJ) may be prepared by treating compounds of formula (BK) with compounds of formula (BL) in the presence of an acid (such as titanium tetrachloride or magnesium iodide) optionally in a suitable solvent (such as dichloromethane) at a temperature between -80 °C and 30 °C (see, for example, Li, W.-D. Z. and Zhang, X.-X. Org. Lett. (2002), 4(20), 3485-3488; Shimada, J. et al. J. Am. Chem. Soc. (1984), 106(6), 1759-73; Eberhardt, U. et. al. Chem. Ber. (1983), 116(1). 119-35 and Wheeler. T. N. US4283348). OSi(R )3 \ OH p,2>V^.Ri Het Q-Wm R^ R' 2^\ OSi(R )3 LA ^^^^ ^ , ^ . O^He. _ (BL) (BK) R P ^ y ^ H e t R R3 (BJ) Compounds of formula (BK) are known or may be made from known compounds by known methods. -67- Compounds of formula (BL) may be prepared from compounds of formula (BM) where in R'" is an alkyl group (preferably methyl) in the presence of chloro tri-Ci-C^alkyl silyl and a metal (preferably sodium) in a suitable solvent (such as toluene or diethyl ether) at a temperature between 20 'C and 150 "C (see, for example, Blanchard, A. N. and Burnell. D. J. Tetrahedron Lett. (2001), 42(29), 4779-4781 and Salaun, J. etal. Tetrahedron (1989), 45(10), 3151-62). R \ l ' / ^2j\ OSi(R )3 RI / \ D1 I Q v / \ X OR- ^ ^ Z~^ 0 R^R' (BM) (BL) Compounds of formula (BM) are analogous to compounds of formula (H) and compounds of fonnula (G) and may be prepared by know methods analogous to those describe for compounds of formula (H) and compounds of fonnula (G). Additional compounds of formula (I) may be prepared wherein R^ and R'' form a bond and R^ is Ci-Cealkylsulfonate (preferably mesylate) or Ci-Cehaloalkylsulfonate (preferably triflate) or an arylsulfonate (preferable tosylate) may be prepared from compounds of formula (BN) following known procedures (Specklin et al. J. Org. Chem. 2008, 73(19), 7845-7848). OG OG R\ 1 R\ 1 R—V'^^^Het R---Y %—Het OH R^ (BN) (I) wherein Ri and R** form a bond Compounds of formula (BM) may be prepared from compounds of formula (BO) under basic or acidic conditions. For example of a procedure see G. Quinkert et al. Helv. Chim. Acta, 1986, 69(3), 469-537. - 6 8 - OG OG R?-\As^Het ^ R—V'^—Het O (BO) (BN) Compounds of formula (BO) may be prepared by reaction of compounds of formula (K) wherein R^ is hydrogen with acids chloride of formula (BP) in the presence of a base. " M IM CI OG R R R\ 1 GO R-V^V-^^e* R ' " V - ^ ^ base 5 ^"^^ °(B0) Compounds of formula (BP) are known or may be made by known methods from known compounds. Alternatively, compounds of formula (BN) can be prepared from compounds of formula (AJ) using known oxidative procedures (see for example D. B. Dess and J. C. Martin J. Org. Chem. 1983. 48 (22), 4155-4156). -69- OG OG R^.-Y'^^Het R---VNs^Het R\^ \_^ —- R\^ y^ Q-cyclopent- 2-enone (150 mg, 0.5 mmol), 1,5-dimethyl-1H-indazole-4-boronic acid (148 mg, 0.78 mmol) and freshly powdered potassium phosphate tribasic (221 mg, 1 mmol) in anhydrous, degassed toluene (1.5 ml) under a nitrogen atmosphere were added palladium acetate (6 mg, 0.03 mmol) and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (21 mg, 0.05 mmol). The reaction was heated to 140 "C for 30 minutes in the microwave (using "normal" absorbtion). The reaction was diluted with water (10 ml) and extracted with ethyl acetate (3x15 ml). The combined organic extracts were washed with brine (10 ml), dried over magnesium sulfate and evaporated to dryness under reduced pressure to give a brown oil. The crude product was purified by column chromatography (30% EtOAc/hexane to 100% EtOAc as eluent) to give 2-(1,5-Dimethyl-1 H-indazol-4-yi)-3-methoxy-5-(tetrahydro-pyran-4-ylmethyl)-cyclopent-2- enone (41 mg). This material was dissolved in acetone (2 ml) and 2 M hydrochloric acid (2 ml) added. This solution was heated in the microwave (using "normal" absorbtion) for 1 h at 120 °C. This solution was then extracted with dichloromethane (2x10 ml) and the organics dried over magnesium sulfate and reduced in vacuo. The crude material was purified by reverse phase preparative HPLC (eluting with acetonitrile/water) to give 2-(1,5-dimethyl-1Hindazol- 4-yl)-4-(tetrahydro-pyran-4-ylmethyl)-cyclopentane-1.3-dione (4 mg). Example2: Preparation of 2-[2-(4-Chloro-phenvn-5-methyl-pvrimidin-4-vl1-4-ftetrahvdro-pvran-4- vlmethvl)-cvclopentane-1.3-dione -98- Step 1: Preparation of 2-(4-Chloro-phenvl)-5-methvl-3H-pvrimidin-4-one o Sodium metal (276 mg. 12 mmol) was added portion wise to ethanol (15 ml) under a nitrogen atmosphere and the mixture allowed to stir at room temperature for 30 minutes until the reaction became homogeneous. 4-Chloro-benzamidine (hydroiodide salt) (1.41 g, 5 mmol) was then added in one portion and the reaction stirred at room temperature for a further 60 minutes. 2-Methyl-3-oxo-propionic acid ethyl ester (716 mg, 5.5 mmol) was finally added drop wise. The reaction was left to stir at room temperature overnight before quenching the reaction slowly with 2M Hydrochloric acid until reaction pH measured pH 1. The resulting precipitate was filtered and air dried, to give 2-(4-Chloro-phenyl)-5-methyl-3H-pyrimidin-4- one as a white solid (570 mg, 2.58 mmol, 52% yield). Step 2: Preparation of 6-Chloro-2-(4-chloro-phenvl)-5-methvl-1 .e-dihydro-pyrimidine CI 2-(4-Chloro-phenyl)-5-methyl-3H-pyrimidin-4-one (570 mg, 2.58 mmol) was suspended in phosphorus oxychloride (2 ml) and heated to reflux for 2 hours. The mixture was cooled before being stripped to dryness in vacuo. The resulting crude product was solubilised in water (10 ml) and ethyl acetate (10 ml) and the biphasic mixture separated. The aqueous layer was further extracted with ethyl acetate (10 ml) before the combined organics were dried with magnesium sulphate, filtered and stripped to dryness in vacuo to give 6-Chloro-2- (4-chloro-phenyl)-5-methyl-1,6-dihydro-pyrimidine as a white solid (667 mg, 2.38 mmol, 92% yield). Step 3: Preparation of 2-f2-(4-Chloro-phenvl)-5-methyl-pyrimidin-4-yn-cvclopentane-1.3-dione -99- To a microwave vial was added 1,3-cyclopentadione (0.5 g, 5.1 mmoi), 6-Chloro-2-(4-chlorophenyl)- 5-methyl-1,6-dihydro-pyrimidine (1.04 g. 4.3 mmol), palladium acetate (58 mg, 0.26 mmol), 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (183 mg, 0.38 mmol), potassium phosphate tribasic (2.49 g, 11.7 mmol) and 1,4-dioxane (10 ml). This was heated in the microwave for 30 minutes at 150°C on a normal setting with a pre-stir of 25 seconds. The resulting slurry was diluted with ethyl acetate (10 ml) and 2M hydrochloric acid (10 ml) before filtering through celite. The filter cake was washed with further ethyl acetate (10 ml) and 2M hydrochloric acid (10 ml).The resulting biphasic mixture was separated and the aqueous layer was extracted with further ethyl acetate (2x10 ml). The combined organic layers were then dried with magnesium sulphate, filtered and stripped to dryness to yield a dark yellow solid. This was purified by normal phase chromatography (gradient system of 100% dichloromethane - 5% methanol: dichloromethane) to give 2-[2-(4-Chloro-phenyl)-5-methylpyrimidin- 4-yl]-cyclopentane-1,3-dione as a yellow solid (348 mg, 1.16 mmol, 22% yield). Step 4: Preparation of 2-f2-(4-Chloro-phenvl)-5-methvl-pvrimidin-4-vl1-3-methoxv-cyclopent-2-enone 2-[2-(4-Chloro-phenyl)-5-methyl-pyrimidin-4-yl]-cyclopentane-1,3-dione (650 mg, 2.16 mmol) was slurried in acetone (20 ml) and potassium carbonate (300 mg, 2.16 mmol) was added. After stirring at room temperature for 5 minutes, dimethyl sulphate (0.20 mi, 2.16 ml) was added in one portion and the reaction was heated to reflux. After 3 hours at reflux the reaction was complete and subsequently cooled to room temperature, before stripping to dryness. The resulting orange solid was re-solubilised in ethyl acetate (20 ml) and 1M sodium hydroxide (20 ml) and the biphasic mixture separated. The aqueous layer was further extracted with ethyl acetate (2x10 ml) before combining the organic layers, drying over magnesium sulphate, filtering and stripping to dryness to isolate a brown solid. This was -100- purified by normal phase chromatography (gradient system of 100% dichloromethane - 5% methanol: dichloromethane) to isolate 2-[2-(4-Chloro-phenyl)-5-methyl-pyrimidin-4-yl]-3- methoxy-cyclopent-2-enone as a yellow foam (526 mg, 1.67 mmol, 77% yield). Step 5: Preparation of 2-f2-(4-Chloro-phenvl)-5-methvl-Pvrimidin-4-yn-5-rhvdroxv-(tetrahvdro-pyran- 4-yl)-methyll-3-methoxv-cvclopent-2-enone HO—/ A solution of 2-[2-(4-Chloro-phenyl)-5-methyl-pyrimidin-4-yl]-3-methoxy-cyclopent-2-enone (69.5 mg, 0.22 mmol) in anhydrous tetrahydrofuran (3 ml), under nitrogen, was cooled to - 78°C and stirred for 10 minutes before the drop wise addition of lithium diisopropylamide (as a 2.0M solution in hexane/tetrahydrofuran/ethylbenzene) (0.14 ml, 0.28 mmol). The resulting brown solution was stirred at -78°C for a further 45 minutes before the drop wise addition of 4-formyltetrahydropyran (34 mg, 0.30 mmol). The orange solution was then warmed to room temperature. After 2.5h the reaction was shown to have reached a steady state and was therefore quenched with saturated ammonium chloride (5ml). ethyl acetate (5 ml) and water (1 ml). The biphasic mixture was separated and the aqueous layer further extracted with ethyl acetate (2x5 mi). Combined organics were dried over magnesium sulphate, filtered and stripped to dryness to yield a yellow oil. This was purified by normal phase chromatography (100% dichloromethane - 5% methanol: dichloromethane) to give 2-[2-(4- Chloro-phenyl)-5-methyl-pyrimidin-4-yl]-5-[hydroxy-(tetrahydro-pyran-4-yl)-methyl]-3- methoxy-cyclopent-2-enone as a dark yellow oil (50.3 mg, 0.12 mmol, 53% yield). Step 6: Preparation of 2-[2-(4-Chloro-phenvl)-5-methvl-pvrimidin-4-vll-4-f1-(tetrahvdro-pvran-4-vl)- meth-(E)-vlidene-cvclopentane-1.3-dione -101- 2-[2-(4-Chloro-phenyl)-5-methyl-pyrimidin-4-yl]-5-[hydroxy-(tetrahydro-pyran-4-yl)-methyl]-3- methoxy-cyclopent-2-enone (50 mg, 0.12 mmol) was solubilised in 1,4-dioxane (2.0 ml) to form a yellow solution. Concentrated hydrochloric acid (20 jxi) was then added in one portion and the resulting orange solution was heated to 60*0. It was stirred at this temperature for 6 hours, adding more concentrated hydrochloric acid after 3 hours (20 \i\) and 4 hours (20 |il), before reaction completion was seen. Reaction was cooled to room temperature and then stripped to dryness to yield 2-[2-(4-Chloro-phenyl)-5-methyl-pyrimidin-4-yl]-4-[1-(tetrahydropyran- 4-yl)-meth-(E)-ylidene-cyclopentane-1,3-dione as a dark orange oil (88 mg, 0.22 mmol, 185% yield). Step 7: Preparation of 2-[2-(4-Chloro-phenvl)-5-methvl-pvrimidin-4-vn-4-(tetrahvdro-pyran-4- vlmethvl)-cvclopentane-1.3-dione 2-[2-(4-Chloro-phenyl)-5-methyl-pyrimidin-4-yl]-4-[1-(tetrahydro-pyran-4-yl)-meth-(E)-ylidenecyclopentane- 1,3-dione (88 mg, 0.22 mmol) was solubilised in ethanol (2.5 ml) and 5% palladium on activated charcoal (4.4 mg, 5% weight relative to starting material) was added. The reaction was stirred at room temperature under 1.5 bar pressure of hydrogen for 14.5 hours, adding more 5% palladium on activated charcoal (4.4 mg, 5% weight relative to starting material) after 7.5 hours. Reaction was then filtered through celite, washing the filter -102- pad with ethanol (10 ml). The resulting solution was stripped to dryness to yield a yellow oil which was purified by reverse phase preparative HPLC (using water, acetonitrile) to give 2- [2-(4-Chloro-phenyl)-5-methyl-pyrimidin-4-yl]-4-(telrahydro-pyran-4-ylmethyl)-cyclopentane- 1,3-dione as a pale yellow oil (9.8 mg, 0.025 mmol, 11% yield). Example 3: Preparation of 2-r2-(4-Chloro-phenvl)-5-methvl-thiazol-4-yl]-4-(tetrahvdro-pvran-4-vlmethvl)- cvclopentane-1.3-dione CI / ^ N O ^ ^ Stepi: Preparation of 2-(4-Chloro-phenyl)-thiazole-5-carbaldehvde O f^\^^^ To a suspension of 4-chlorophenyl thioamide (lOg, 58.2mmol) in 1,2-dimethoxyethane (80ml) was added 2-chloromalonaldehyde (11.3g, 87.3mmol), followed by magnesium carbonate hexahydate (14.12g, 30.8mmol), and the reaction heated to 60°C under nitrogen for 3 hours. The crude reaction mixture was filtered through a plug of silica (50g), washed with ethyl acetate, and the combined filtrate concentrated under reduced pressure to give 2-(4-Chloro-phenyl)-thiazole-5- carbaldehyde (7.66g). Step 2: Preparation of [2-(4-Chloro-phenvl)-thia20l-5-yl1-methanol - 1 0 3 - To a solution of 2-(4-Chloro-phenyl)-thiazole-5-carbaldehyde (5.59g, 25mmol) in methanol (65ml) at 0°C was added sodium borohydride (1.04g, 27.5mmol) portionwise over a period of 5 minutes. The reaction was then allowed to warm to room temperature and stirred under nitrogen for 3 hours. The reaction was quenched with saturated aqueous ammonium chloride solution (100ml) and stirred for 5 minutes, before the methanol was removed under reduced pressure. The resulting heterogeneous mixture was then extracted with ethyl acetate (2 x 100ml), the combined organics dried over magnesium sulphate and the solvent removed under reduced pressure to give [2-{4-Chloro-phenyl)-thiazol-5-yl]-methanol (5.27g). Step 3: Preparation of 3-f2-(4-Chloro-phenyl)-thiazol-5-ylmethoxv1-cyclopent-2-enone O To a solution of [2-(4-Chloro-phenyl)-thiazol-5-yl]-methanol (2g, 8.8mmol) in anhydrous THF (50ml), at 0°C, under an atmosphere of nitrogen was added cyclopentane-1,3-dione (1.12g, 11.4mmol), followed by triphenylphosphine (2.99g, 11.4mmol). Diisopropylazodicarboxylate (2.2ml, 11.4mmol) was then added dropwise over a period of 5 minutes and the reaction allowed to warm to room temperature and stirred for 2 hours. The crude reaction mixture was dry loaded onto silica and purified by flash chromatography to give 3-[2-(4-Chloro-phenyl)-thiazol-5- ylmethoxy]-cyclopent-2-enone (2.12g). Step 4: Preparation of 2-[2-(4-Chloro-phenvlV5-methvl-thiazol-4-vl]-cvclopentane-1.3-dione -104- To a solution of 3-[2-(4-Chloro-phenyl)-thiazol-5-ylmethoxy]-cyclopent-2-enone (1.29g, 4.22mmol) in ethylene glycol dimethyl ether (10ml) was added 1-butyl-3-methylimidazolium bis(trifluoromethylsulphonyl) imide (lOOjil) and the reaction heated to 230°C by microwave irradiation for 30 minutes. The crude reaction mixture was dry loaded onto silica and purified by flash chromatography to give 2-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-cyclopentane-1,3- dione(1.12g). Step 5: Preparation of 2-f2-(4-Chloro-phenvl)-5-methvl-thiazol-4-vl1-3-methoxv-cvclopent-2-enone 0-0 To a solution of 2-[2-{4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-cyclopentane-1,3-dione (1.12g, 3.66mmol) in acetone (20ml) was added potassium carbonate (1.04g, 7.32mmol), followed by iodomethane (455^1, 7.32mmol), and the reaction heated to 40°C for 6 hours. The solvent was then removed from the crude reaction mixture under reduced pressure and the residue partitioned between water (100ml) and ethyl acetate (100ml). The organic layer was separated, dry loaded onto silica and purified by flash chromatography to give 2-[2-(4-Chloro-phenyl)-5- methyl-thiazol-4-yl]-3-methoxy-cyclopent-2-enone(780mg). Step 6: Preparation of 2-[2-(4-Chloro-phenvl)-5-methvl-thiazol-4-yi]-3-methoxv-5-[1-(tetrahydro-pvran-4- vn-meth-(E)-vlidenel-cvclopent-2-enone -105- o >-N To a solution of 2-[2-(4-Chloro-phenyl)-5-methyl-thia2ol-4-yl]-3-methoxy-cyclopent-2-enone {640mg, 2mmol) in anhydrous tetrahydrofuran (12mi) at -78*C under an atmosphere of nitrogen was added lithium diisopropylamide (1.8M in THF/heptanes/ethylbenzene; 1.1ml, 2mmol) dropwise over a period of 5 minutes, and the reaction allowed to stir at 78°C for 30 minutes. A solution of tetrahydro-pyran-4-oarbaldehyde (228mg, 2mmbl) in anhydrous tetrahydrofuran (1ml) was then added dropwise over a period of 5 minutes t)efore the reaction is allowed to warm to room temperature and stirred for a further 30 minutes. Potassium fert-butoxide (337mg, 3 mmol) was then added in one portion and the reaction stirred for a further 90 minutes. The reaction was quenched by the addition of saturated aqueous ammonium chloride solution (50ml) and extracted with ethyl acetate (50ml) and the organic later separated, dry loaded onto silica and purified by flash chromatography to give 2-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-3-methoxy-5-[1- (tetrahydro-pyran-4-yl)-meth-(E)-ylidene]-cyclopent-2-enone(195mg). Step 7: Preparation of 2-f2-(4-Chloro-phenvl)-5-methyl-thiazol-4-vn-4-[1-(tetrahvdro-pvran-4-yl)-meth-(E)- vlidene1-cvclopentane-1.3-dione O >-N To a solution of 2-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-3-methoxy-5-[1-{tetrahydro-pyran-4- yl)-meth-(E)-ylidene]-cyclopent-2-enone (190mg, 0.45mmol) in acetone (2ml) was added 2N hydrochloric acid (2ml) and the reaction heated to 120°C for 30 minutes by microwave irradiation. The crude reaction was diluted with ethyl acetate (25ml) and washed with saturated aqueous -106- ammonium chloride solution {25ml), brine (25ml) and the organic later separated, dried over magnesium sulphate and the solvent removed under reduced pressure to give 2-[2-(4-Chlorophenyl)- 5-methyl-thiazol-4-yl]-4-[1-(tetrahydro-pyran-4-yl)-meth-(E)-ylidene]-cyclopentane-1,3- dione (168mg). Step 8: Preparation of 2-f2-(4-Chloro-phenyl)-5-methvl-thiazol-4-vl1-4-(tetrahydro-Pvran-4-vlmethvl)- cyclopentane-1.3-dione O >-N To a solution of 2-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-4-[1-(tetrahydro-pyran-4-yl)-meth- (E)-ylidene]-cyclopentane-1,3-dione (130mg, 0.32mmol) in ethanol (2ml) was added 5% palladium on carbon (13mg), and the reaction stirred under an atmosphere hydrogen at a pressure of 2 bar for 4 hours. The crude reaction mixture was filtered through a pad of Celite and purified by preparative mass-directed HPLC to give 2-[2-{4-Chloro-phenyl)-5-methyl-thiazol-4-yl]- 4-(tetrahydro-pyran-4-ylmethyl)-cyclopentane-1,3-dione (30mg). Preparation of 2-f2-(4-Chloro-phenvn-5-methvl-thiazol-4-vl1-4-(5-fluoro-pvridin-2-yimethvl)- cvclopentane-1.3-dione CI SteoJ: -107- Preparationof 2-[2-(4-Chloro-phenvn-5-methvl-thiazol-4-vll-5-f(5-fluoro-pvridin-2-yl)-hvdroxymethvl)- 3-methoxv-cvclopent-2-enone CI To a solution of 2-[2-(4-Chloro-phenyl)-5-methyl-thia20l-4-yl]-3-methoxy-cyclopent-2-enone (400mg, 1.25mmol) in anhydrous tetrahydrofuran (10ml) at -78°C under an atmosphere of nitrogen was added lithium diisopropylamide (1.8M in THF/heptanes/ethylbenzene ; 0.76ml, 1.37mmol) dropwise over a period of 5 minutes, and the reaction allowed to stir at 78°C for 30 minutes. A solution of 5-fluoro-pyridine-2-carbaldehyde (17lmg. 1.37mmol) in anhydrous tetrahydrofuran (1ml) was then added dropwise over a period of 5 minutes ttefore the reaction was allowed to warm to room temperature and stirred for a further 30 minutes. The reaction was quenched by the addition of saturated aqueous ammonium chloride solution (50ml) and extracted with ethyl acetate (50ml) and the organic later separated, dry loaded onto silica and purified by flash chromatography to give 2-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-5-[(5-fluoro-pyridin-2- yl)-hydroxy-methyl)-3-methoxy-cyclopent-2-enone(400mg). -108- Step 2: Preparation of 2-f2-(4-Chloro-phenvl)-5-methvl-thiazol-4-vn-4-ri-(5-fluoro-pvridin-2-vl)-meth-(E)- ylidenel-cvclopentane-l .S-dione CI / ^ N O To a solution of 2-[2-(4-Chioro-phenyi)-5-methyl-thiazol-4-yl]-3-methoxy-5-[1-(tetrahydro-pyran-4- yl)-meth-(E)-ylidene]-cyclopent-2-enone (190mg, 0.45mmol) in acetone (2ml) was added 2N hydrochloric acid (2ml) and the reaction heated to 130°C for 90 minutes by microwave irradiation. The crude reaction is then dry loaded onto silica and purified by flash chromatography to give 2- [2-(4-Chloro-phenyl)-5-methyl-thia2ol-4-yl]-4-[1-(5-fluoro-pyridin-2-yl)-meth-(E)-ylidene]- cyciopentane-1,3-dione (93mg). Step 3: Preparation of 2-f2-(4-Chloro-phenyl)-5-methvl-thiazol-4-vl]-4-(5-fluoro-pvridin-2-vlmethvl)- cvclopentane-1 .S-dione CI /^N O To a solution of 2-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-4-[1-(5-fiuoro-pyridin-2-yl)-meth-(E)- yiidene]-cyclopentane-1,3-dione (70mg, 0.17mmol) in glacial acetic acid (2ml) was added zinc powder (10mg), and the reaction heated to 80°C for 17 hours. The crude reaction mixture was then dry loaded onto silica and purified by flash chromatography to give 2-[2-(4-Chloro-phenyl)-5- methyl-thiazol-4-yl]-4-(5-fluoro-pyridin-2-ylmethyl)-cyclopentane-1.3-dione(55mg). -109- Preparation of 2-f2-(4-Chloro-phenvl)-5-ethvl-thiazol-4-yl1-4-ri-(tetrahvclro-pvran-4-vl)-meth-(E)- ylidenel-cvclopentane-l .3-dione CI MN 0 Step1: Preparation of 2-(4-Chloro-phenyn-thiazole-5-carbalclehyde H \\ / / ^ ^ To a suspension of 4-chlorophenyl thioamide (lOg, 58.2mmol) in 1,2-dimethoxyethane (80ml) was added 2-chloromalonaldehyde (11.3g, 87.3mmol), followed by magnesium carbonate hexahydrate (14.12g, 30.8mmol), and the reaction heated to 60°C under an atmosphere of nitrogen for 3 hours. The crude reaction mixture is filtered through a plug of silica (50g), which wass washed with ethyl acetate, and the combined filtrate concentrated under reduced pressure to give 2-(4-Chloro-phenyl)-thia2ole-5-carbaldehyde (7.66g). Step 2: Preparation of 1-f2-(4-Chloro-phenyn-thiazol-5-yn-ethanol To a solution of 2-(4-Chloro-phenyl)-thiazole-5-carbaldehyde (4.95g, 22.14mmol) in THF (65ml) at 0°C under an atmosphere of nitrogen was added methyl magnesium chloride (3M in THF; -110- 8.11ml, 24.35mnriol) dropwise over a period of 5 minutes. The reaction was then allowed to warm to room temperature and stirred for a further 2 hours. The reaction was quenched with saturated aqueous ammonium chloride solution (100ml) and stirred for 5 minutes, before the methanol is removed under reduced pressure. The resulting heterogeneous mixture was then extracted with ethyl acetate (2 x 100ml), the combined organics dried over magnesium sulphate and the solvent removed under reduced pressure to give 1-[2-(4-Chloro-phenyl)-thiazol-5-yl]-ethanol (4.71g). Step 3: Preparation of 3-(1 -[2-f4-Chloro-phenyl)-thia20l-5-yl1-ethoxy}-cyclopent-2-enone O To a solution of 1-[2-(4-Chloro-phenyl)-thiazol-5-yl]-ethanol (4.1g, 17.1mmol) in anhydrous THF (100ml), at 0°C under an atmosphere of nitrogen was added cyclopentane-1,3-dione (2.18g, 22.23mmol), followed by triphenylphosphine (5.83g, 22.23mmol). Diisopropylazodicarboxylate (4.31ml, 22.23mmol) wss then added dropwise over a period of 5 minutes and the reaction allowed to warm to room temperature and stirred for 2 hours. The cmde reaction mixture was dry loaded onto silica and purified by flash chromatography to give 3-{1-[2-{4-Chloro-phenyl)-thiazol- 5-yl]-ethoxy}-cyclopent-2-enone(2.29g). Step 4: Preparation of 2-f2-(4-Chloro-phenyl)-5-ethvl-thia2ol-4-vl1-cyclopentane-1 •3-dione tic To a solution of 3-{1-[2-(4-Chloro-phenyl)-thia2ol-5-yl]-ethoxy}-cyclopent-2-enone (2.29g, 7.16mmol) in ethylene glycol dimethyl ether (10ml) was added 1-butyl-3-methylimidazolium bis(trifluoromethylsulphonyl) imide (100^1) and the reaction heated to 230°C by microwave irradiation for 30 minutes. The crude reaction mixture was dry loaded onto silica and purified by - 1 1 1 - flash chromatography to give 2-[2-<4-Chloro-phenyl)-5-ethyl-thiazol-4-yl]-cyclopentane-1.3-dione (681 mg). Step 5: Preparation of 2-f2-(4-Chloro-phenyl)-5-ethvl-thiazol-4-vl]-3-methoxv-cvclopent-2-enone a, To a solution of 2-[2-(4-Chloro-phenyl)-5-ethyi-thiazol-4-yl]-cyclopentane-1,3-clione (650mg, 2.03mnnol) in acetone (10ml) was added potassium carbonate (553mg, 4mmol), followed by iodomethane (248^1, 4mnriol), and the reaction heated to 40°C for 6 hours. The solvent was then removed from the crude reaction mixture under reduced pressure and the residue partitioned between water (100ml) and ethyl acetate (100ml). The organic layer was separated, dry loaded onto silica and purified by flash chromatography to give 2-[2-(4-Chloro-phenyl)-5-ethyl-thiazol-4- yl]-3-methoxy-cyclopent-2-enone(395mg). Step 6: Preparation of 2-r2-(4-Chloro-phenvl)-5-ethvl-thiazol-4-vl]-5-[hvdroxv-(tetrahvdro-pvran-4-vl)- methyl]-3-methoxv-cvclopent-2-enone O >-N To a solution of 2-[2-(4-Chloro-phenyl)-5-ethyl-thiazol-4-yl]-3-methoxy-cyclopent-2-enone (175mg, 0.52mmol) in anhydrous tetrahydrofuran (5ml) at -78°C under an atmosphere of nitrogen was added lithium diisopropylamide (1.8M in THF/heptanes/ethylbenzene; 1.1ml, -112- 2mmol) dropwise over a period of 1 minute and the reaction allowed to stir at 78°C for 40 minutes. A solution of tetrahydro-pyran-4-carbaldehyde {228mg, 2mmoi) in anhydrous tetrahydrofuran (Imi) was then added dropwise over a period of 30 seconds before the reaction was allowed to warm to room temperature and stirred for a further 30 minutes. The reaction was quenched by the addition of saturated aqueous ammonium chloride solution (50ml) and extracted with ethyl acetate (50ml) and the organic layer separated, dry loaded onto silica and purified by flash chromatography to give 2-[2-(4-Chloro-phenyl)-5-ethyl-thiazol-4-yl]-5-[hydroxy-(tetrahydropyran- 4-yl)-methyl]-3-methoxy-cyclopent-2-enone(86mg). Step 7: Preparation of 2-f2-(4-Chloro-phenvl)-5-ethvl-thia2ol-4-vl1-4-[1-(tetrahydro-pyran-4-vl)-meth-(E)- ylidene]-cvclopentane-1,3-dione O >-N O To a stirred solution of 2-[2-(4-Chloro-phenyl)-5-ethyl-thiazol-4-yl]-3-methoxy-5-[1-(tetrahydropyran- 4-yl)-meth-(E)-ylidene]-cyclopent-2-enone (85mg, 0.19mmol) in 1,4-dioxane (3ml) was added 12M hydrochloric acid (32jil, 0.38mmol) and the reaction heated to 60°C for 12 hours. The solvent was removed under reduced pressure and the residue purified by mass-directed preparative HPLC to give 2-[2-(4-Chloro-phenyl)-5-ethyl-thiazol-4-yl]-4-[1-(tetrahydro-pyran-4-yl)- meth-(E)-ylidene]-cyclopentane-1,3-dione (4mg). Example 4: Preparation of 2-f5-(4-Chloro-phenvl)-2-methyl-thiophen-3-vl1-4-ftetrahydro-Pvran-4-vlmethvl)- cvclopentane-1 •3-dione - 1 1 3 - CI Stepi: Preparation of f5-(4-Chloro-phenvl)-thiophen-2-vll-methanol To a solution of 5-(4-Chloro-phenyl)-thiophene-2-Garbalclehyde (5g, 22.45nnnnol) in methanol (250nnl) at 0°C under an atmosphere of nitrogen was added sodium borohydride (1.02g, 26.94mmol) portionwise over a period of 5 minutes. The reaction was then allowed to warm to room temperature and stin^ed for 3 hours. The reaction was quenched with saturated aqueous ammonium chloride solution (100ml) and stirred for 5 minutes, before the methanol is removed under reduced pressure. The resulting heterogeneous mixture was then extracted with ethyl acetate (2 x 100ml), the combined organics dried over magnesium sulphate and the solvent removed under reduced pressure to give [5-(4-Chloro-phenyl)-thiophen-2-yl]-methanol (4.89g). Step 2: Preparation of 3-('5-(4-Chloro-phenyl)-thiophen-2-ylmethoxv]-cvclopent-2-enone o -114- To a solution of [2-(4-Chloro-phenyl)-thiazol-5-yl]-methanol (4.89g. 21.75mmol) in anhydrous THF (100ml), at 0°C under.an atmosphere of nitrogen was added cyclopentane-1,3-dione (2.78g. 28.27mmol) followed by triphenylphosphine (7.41g, 28.27mnnol). Diisopropylazodicarboxylate {5.48ml, 28.27mmol) was then added dropwise over a period of 5 minutes and the reaction allowed to warm to room temperature and stirred for 2 hours. The crude reaction mixture was dry loaded onto silica and purified by flash chromatography to give 3-[5-(4-Chloro-phenyl)-thiophen-2- ylmethoxy]-cyclopent-2-enone (5.1 g). Step 3: Preparation of 2-f5-(4-Chloro-phenvlV2-methvl-thiophen-3-yl1-cyclopentane-1.3-dione To a solution of 3-[5-(4-Chloro-phenyl)-thiophen-2-ylmethoxy]-cyclopent-2-enone (4.89, 4.22mmol)in 1,2-diemethoxyethane (10ml) was added 1-butyl-3-methylimidazolium bis(trifluoromethylsulphonyl) imide (100^l) and the reaction heated to 180°C by microwave irradiation for 30 minutes. The crude reaction mixture was dry loaded onto silica and purified by flash chromatography to give 2-[5-(4-Chloro-phenyl)-2-methyl-thiophen-3-yl]-cyclopentane-1,3- dione (2.21g). Step 4: Preparation of 2-[5-(4-Chloro-phenvl)-2-methvl-thiophen-3-vn-3-methoxv-cvclopent-2-enone f^^V-CI To a solution of 2-[5-(4-Chloro-phenyl)-2-methyl-thiophen-3-yl]-cyclopentane-1,3-dione (2.21g, 7.25mmol) in acetone (50ml) was added potassium carbonate (1514g, 10.87mmol) followed by iodomethane (670^1,10.87mmol) and the reaction heated to 40°C for 6 hours. The solvent was then removed from the crude reaction mixture under reduced pressure and the residue partitioned between water (100ml) and ethyl acetate (100ml). The organic layer was seperated, -115- dry loaded onto silica and purified by flash chromatography to give 2-[5-(4-Chloro-phenyl)-2- methyl-thiophen-3-yl]-3-methoxy-cyclopent-2-enone (818mg). Step 5: Preparation of 2-f5-(4-Chloro-phenvl)-2-methvl-thiophen-3-yn-5-fhvdroxy-(tetrahvdro-pvran-4-vnmethvn- 3-methoxv-cvclopent-2-enone To a solution of 2-[5-(4-Chloro-phenyl)-2-methyl-thiophen-3-yl]-3-methoxy-cyclopent-2-enone (255mg, O.Bmmol) in anhydrous tetrahydrofuran (6ml) at -78°C under an atmosphere of nitrogen was added lithium diisopropylamide (1.8M in THF/heptanes/ethylbenzene; 0.49ml, 0.89mmol) dropwise over a period of 5 minutes and the reaction allov/ed to stir at 78°C for 30 minutes. A solution of tetrahydro-pyran-4-carbaldehyde (102mg, 0.89mmol) in anhydrous tetrahydrofuran (1ml) was then added dropwise over a period of 5 minutes before the reaction was allowed to warm to room temperature and stirred for a further 30 minutes. The reaction was quenched by the addition of saturated aqueous ammonium chloride solution (50ml) and extracted with ethyl acetate (50ml) and the organic later separated, dry loaded onto silica and purified by flash chromatography to give 2-[5-(4-Chloro-phenyl)-2-methyl-thiophen-3-yl]-5-[hydroxy-(tetrahydropyran- 4-yl)-methyl]-3-methoxy-cyclopent-2-enone(292mg). Step 6: Preparation of 2-f5-(4-Chloro-phenyl)-2-methvl-thiophen-3-yn-4-f 1 -(tetrahvdro-pvran-4-vl)-meth- (E)-ylidene]-cvclopentane-1.3-dione -116- To a solution of 2-[5-(4-Chloro-phenyl)-2-methyl-thiophen-3-yl]-5-[hydroxy-(tetrahydro-pyran-4-yl)- methyl]-3-methoxy-cyclopent-2-enone {280mg, 0.65mmol) in acetone {2ml) was added 2N hydrochloric acid (2ml) and the reaction heated to 120°C for 60 minutes by microwave irradiation. The crude reaction was diluted with ethyl acetate (25ml) and washed with saturated aqueous ammonium chloride solution (25ml). brine (25ml) and the organic layer dry loaded onto silica and purified by flash chromatography to give 2-[5-(4-Chloro-phenyl)-2-methyl-thiophen-3-yl]-4-[1- (tetrahydro-pyran-4-yl)-meth-(E)-ylidenel-cyclopentane-1,3-dione (88mg). Step 7: Preparation of 2-f5-(4-Chloro-phenvl)-2-methvl-thiophen-3-vn-4-^tetrahvdro-pvran-4-vlmethyncvclopentane- 1.3-dione rCI u To a solution of 2-[5-(4-Chloro-phenyl)-2-methyl-thiophen-3-yl]-4-f1-(tetrahydro-pyran-4-yl)-meth- (E)-ylidene]-cyclopentane-1,3-dione (88mg, 0.22mmol) in ethanol (2ml) was added 5% palladium on carbon (9mg) and the reaction stirred under an atmosphere of hydrogen at a pressure of 2 bar for 4 hours. The crude reaction mixture was filtered through a pad of Celite and purified by preparative mass-directed HPLC to give 2-[5-(4-Chloro-phenyl)-2-methyl-thiophen-3-yl]-4- (tetrahydro-pyran-4-ylmethyl)-cyclopentane-1,3-dione (43mg). Preparation of 2-f5-(4-Chloro-phenvn-2-methyl-thiophen-3-vl1-4-(tetrahvdro-furan-3-vlmethvl)- cyclopentane-1 •3-dione CI V-o -117- Step1: Preparation of 2-f5-(4-Chloro-phenyl)-2-methvl-thiophen-3-vl1-3-methoxv-5-(tetrahydro-furan-3- ylmethvn-cvclopent-2-enone To a solution of 2-[5-(4-Chloro-phenyl)-2-methyl-thiophen-3-yl]-3-methoxy-cyclopent-2-enone (285mg. 0.89mmol) in anhydrous tetrahydrofuran (6ml) at -78°C under an atnnosphere of nitrogen is added lithium diisopropylamide (1.8M in THF/heptanes/ethylbenzene; 0.55ml, 1 .Ommol) dropwise over a period of 5 minutes and the reaction allowed to stir at -78°C for 30 minutes. A solution of 3-iodomethyl tetrahydrofuran (212mg, 1mmol) in anhydrous tetrahydrofuran (1ml) was then added dropwise over a period of 5 minutes before the reaction was allowed to warm to room temperature and stirred for a further 30 minutes. The reaction was quenched by the addition of saturated aqueous ammonium chloride solution (50ml) and extracted with ethyl acetate (50ml) and the organic later separated, dry loaded onto silica and purified by flash chromatography to give 2-[5-(4-Chloro-phenyl)-2-methyl-thiophen-3-yl]-3-methoxy-5-(tetrahydro-furan-3-ylmethyl)- cyclopent-2-enone (150mg) Step 2: Preparation of 2-f5-(4-Chloro-phenyl)-2-methyl-thiophen-3-vll-4-(tetrahvdro-furan-3-vlmethvlV cvclopentane-1 .S-dione /•^%-CI To a solution of 2-[5-(4-Chloro-phenyl)-2-methyl-thiophen-3-yl]-3-methoxy-5-(tetrahydro-furan-3- ylmethyl)-cyclopent-2-enone (150mg, 0.37mmol) in acetone (2ml) was added 2N hydrochloric -118- acid (2ml) and the reaction heated to 120°C for 60 minutes by microwave irradiation. The crude reaction was diluted with ethyl acetate (25ml) and washed with saturated aqueous ammonium chloride solution (25ml), brine (25ml). The solvent was removed under reduce pressure and the residue purified by mass-directed preparative HPLC to give 2-[5-(4-Chloro-phenyl)-2-methylthiophen- 3-ylH-(tetrahydro-furan-3-ylmethyl)-cyclopentane-1.3-dione(15mg). Compounds characterised by HPLC-MS were analysed using one of three methods described below. Method A Compounds characterised by HPLC-MS were analysed using a Waters 2795 HPLC equipped with a Waters Atlantis dCI 8 column (column length 20 mm, internal diameter of column 3 mm, particle size 3 micron, temperature 40 °C). Waters photodiode an-ay and Micromass ZQ2000. The analysis was conducted using a three minutes run time, according to the following gradient table: Time(mins) Solvent A (%) Solvent B(%) Flow (ml/mn) 0.00 90.0 10.0 2.00 0.25 90.0 10.0 2.00 2.00 10.0 90.0 2.00 2.50 10.0 90.0 2.00 2.60 90.0 10.0 2.00 3.0 90.0 10.0 2.00 Solvent A: H2O containing 0.1% HCOOH Solvent B: CH3CN containing 0.1% HCOOH Method B Compounds characterised by HPLC-MS were analysed using an Waters 2777 injector with a 1525 micro pump HPLC equipped with a Waters Atlantis dC18 IS column (column length 20 mm, -119- internal diameter of column 3 mm. particle size 3 micron), Waters 2996 photodiode array, Waters 2420 ELSD and Micromass ZQ2000. The analysis was conducted using a three minutes run time, according to the following gradient table: Time Solvent A Solvent B Flow (ml/mn) (mins) (%) (%) "OOO 95^0 5 1.300 2.50 OOO 100 1.300 TSO OOO iOO 1.300 2.90 95!0 5 1.300 Solvent A: H2O with 0.05% TFA Solvent B: CH3CN with 0.05% TFA Method C: Compounds characterised by HPLC-MS were analysed using a Finnigan Surveyor MSQ Plus equipped with a Waters Xterra column (column length 50 mm, internal diameter of column 4.6 mm, particle size 3.5 micron, temperature 40 "C). Waters photodiode array and Micromass ZQ2000. The analysis was conducted using a six minutes run time, according to the following gradient table: Time (mins) Solvent A (%) Solvent B(%) Flow (ml/mn) 0.00 90.0 10.0 1.30 3.80 0.00 100 1.30 4.80 0.00 100 1.30 5.00 90.0 10.0 1.30 6.00 90.0 10.0 1.30 Solvent A: H2O containing 0.05% HCOOH Solvent B: CH3CN containing 0.05% HCOOH -120- Method D Compounds characterised by UPLC-MS were analysed using a Waters Acquity UPLC equipped with a Waters Atlantis dC18 column (column length 20 mm, internal diameter of column 3 mm, particle size 3 micron, temperature 40 °C), Waters photodiode anray and Micromass ZQ2G00. The analysis was conducted using a two minute run time, according to the following gradient table: Time (mins) Solvent A (%) Solvent B (%) Flow (ml / mn) 0.00 90.0 10.0 2.00 1.50 10.0 90.0 2.00 1.75 10.0 90.0 2.00 1.9 90.0 10.0 2.00 2.00 90.0 10.0 2.00 Solvent A: H2O containing 0.1% HCOOH Solvent B: CH3CN containing 0.1% HCOOH -121 - Table A1 Compound Structure LC/MS, NMR or Number other physical data A1 /"'^-''V-^ V- LC/MS (Method D) ^ S c P v / ^ ES*:MH* = 410 o X A rt=1.43min A2 /""VN-^ V- LC/MS (Method D) ° ^ X / O . ES*: MH* = 434. j y ^ rt=1.03min A3 r'N'^'^V-^ V LC/MS (Method D) ^ Xy^lX ES^MH^=432. W 7 rt=1.16min A4 r^N^'V-^ )- LC/MS (Method D) ° ^ V ^ ^ ES-:MH-=447, Br rt=1.12min A5 /\/\ 11 V LC/MS (Method D) 2* rt= 0.94 min A6 r^\^"\^ X- LC/MS (Method D) o Xi ^^^ CI rt= 0.99 min A7 Q / LC/MS (Method D) ° K^ rt= 1.35 min I CI j -122- A8 r'N'^N-/ ^ = \ LC/MS (Method D) ° ^ L / ^ / ES*:MH* = 399, \_/ rt= 1.00 min CI A9 r'N-'V^ V=\ LC/MS (Method D) o . ] L / ^ / ES*:MH* = 397. \ _ _ / rt= 1.04 min CI A10 r ' N ^ ^ ^ V- LC/MS (Method D) °^ S < C 1 ^ ES*: MH* = 401, o T^ ^^^ CI rt= 1.01 min A11 /^..^-^ // V LC/MS (Method D) \ = ^ L / - < J ES*: MH* = 384. CI rt= 1.36 min A12 r-^^..,--v J V LC/MS (Method D) F - \ ^ N L / \ J L ES*: MH* = 415, CI rt= 1.03 min A13 (T^^'^-r^ y^ LC/MS (Method D) F ^ \ ^N L V A ^ J ES*:MH' = 413. ^ CI rt= 1.03 min I LC/MS (Method D) r / ES*:MH' = 413, I /? \ ^""^ |y__/~~"? rt= 1.41 min A14 I ^^c. I -123- f^ LC/MS (Method D) S ^ ^ o ES*:MH* = 395. S ^ Vs 397 [ /-< I W^ N^=\.^x, rt=1.24min .A15 ^^c. : ^-'V^.-N^y? V LC/MS (Method D) \ ^N L / ~ \ J ES*: MH* = 397. A16 ^ CI rt= 0.79 min ^ V ^ s ^ j ^ V LC/MS (Method D) ° - ^ X ^ ~ v L ^ ES^MH^ = 370 b [' ] rt= 1.02 min A17 2^ ^ - s / ^ ^ ^ ^ \ LC/MS (Method D) A18 ^ ^ rt= 1.12 min o -R' / I where G, is hydrogen, and R^ and R^ are as described in Table 1. -144- Table 47 covers 98 compounds of the following type H where G, is hydrogen, and R* and R^ are as described in Table 1. Table 48 covers 98 compounds of the following type GO // \ 7 F where G, is hydrogen, and R^ and R^ are as described in Table 1. Table 49 covers 98 compounds of the following type R \ JL -x^R CI where G. is hydrogen, and R® and R^ are as described in Table 1. Table 50 covers 98 compounds of the following type -145- where G, is hydrogen, and R^ and R^ are as described in Table 1. Table 51 covers 98 compounds of the following type where G, is hydrogen, and R® and R^ are as described in Table 1. Table 52 covers 98 compounds of the following type GO 1/ \ 7 V JL >x^R where G, is hydrogen, and R^ and R^ are as described in Table 1. Table 54 covers 98 compounds of the following type -146- where G, is hydrogen, and R^ and R^ are as described in Table 1. Table 55 covers 98 compounds of the following type / where G. is hydrogen, and R® and R^ are as described in Table 1. Biological Examples Example A: Seeds of a variety of test species are sown in standard soil in pots. After cultivation for one day (pre-emergence) or after 8 days cultivation (post-emergence) under controlled conditions in a glasshouse (at 24/16°C, day/night; 14 hours light; 65 % humidity), the plants are sprayed with an aqueous spray solution derived from the formulation of the technical active ingredient in acetone / water (50:50) solution containing 0.5% Tween 20 (polyoxyethyiene sorbitan monolaurate, CAS RN 9005-64-5). The test plants are then grown in a glasshouse under controlled conditions in a glasshouse (at 24/16°C, day/night; 14 hours light; 65 % humidity) and watered twice daily. After 13 days for pre and post-emergence, the test is evaluated (100 = total damage to plant; 0 = no damage to plant). -147- Test plants: Lolium perenne (LOLPE), Alopecurus myosuroides (ALOMY), Echinochloa crus-galli (ECHCG), Avena fatua (AVEFA) Post-Emergence Activity I j I I I Compound Rate g/ LOLPE ALOMY ECHCG AVEFA Number ha A1 250 0 10 10 0 A2 250 10 10 20 0 A3 250 0 10 20 0 A4 250 0 20 70 0 AS 250 30 50 80 50 A6 250 0 50 60 0 A7 250 60 90 100 100 A8 250 50 50 90 50 A9 250 40 20 100 60 A10 250 10 20 70 0 A11 250 0 10 80 0 A12 250 100 100 100 90 A13 250 0 10 20 10 A15 250 0 10 20 0 A16 250 100 90 100 100 A17 250 100 90 100 90 A18 250 100 100 100 100 A19 250 0 20 40 10 A20 250 90 80 100 90 A21 250 60 70 90 30 A22 250 50 70 90 60 A23 250 100 90 100 100 A24 250 90 100 100 90 A25 I 250 I 100 I 100 j 100 | 100 Pre-Emergence Activity -148- Compound Rate g/ha LOLPE ALOMY ECHCG AVEFA Number A1 10 10 50 0 A1 A7 80 70 100 70 A7 A8 80 50 100 60 A8 A9 70 10 100 50 A9 A12 100 100 100 90 A12 A16 90 90 100 80 A16 A17 100 70 100 50 A17 A18 100 80 100 90 A18 A20 70 40 100 20 A20 A21 90 40 90 10 A21 A22 60 40 70 20 A22 A23 100 90 100 90 A23 A24 100 60 100 60 A24 A25 90 70 100 70 A25 EXAMPLE B: Seeds of the Winter Wheat variety 'Hereward' were sown in standard soil in pots. After 8 days cultivation under controlled conditions in a glasshouse (at 24/16°C, day/night; 14 hours light; 65 % humidity), the plants were sprayed post-emergence with an aqueous spray solution derived from the formulation of the technical active ingredient in acetone / water (50:50) solution containing 0.5% Tween 20 (polyoxyethylene sorbitan monolaurate, CAS RN 9005-64-5). Seeds of the Winter Wheat variety 'Hereward' were seed treated with a wettable powder formulation of the cereal herbicide safener, cloquintocet mexyl, at a rate of 0.5 grams per kilogram of dry seed prior to the initiation of glasshouse testing. One seed was sown per 1.5 inch plastic pot into a sandy loam soil at a depth of 1cm, 8 days prior to application of the test compounds and was watered and grown under controlled conditions in a glasshouse (at 24/16°C, day/night; 14 hours light; 65 % humidity). The plants were sprayed postemergence with an aqueous spray solution derived from the formulation of the technical active ingredient in acetone / water (50:50) solution containing 0.5% Tween 20 (polyoxyethylene sorbitan monolaurate, CAS RN 9005-64-5). -149- The test plants were then grown in a glasshouse under controlled conditions in a glasshouse (at 24/16°C, day/night; 14 hours light; 65 % humidity) and watered twice daily. After 13 days for pre and post-emergence, the test was evaluated (100 = total damage to plant; 0 = no damage to plant). Compound Rate Winter Wheat Winter Wheat Number g/ha (Hereward) (Hereward) + cloquintocet mexyl A1 250 20 g_ A6 250 10 0^ A7 250 90 40 A8 250 20 0_ A9 250 50 0_ A12 250 70 80 A15 250 10 0_ A16 250 60 60 A17 250 60 40 A18 250 80 90 A20 250 70 70_ A21 250 20 1^ A22 250 60 10_ A23 250 80 60, A24 250 70 g_ A25 I 250 I 80j 40_ - 150- CLAIMS: 1. A compound of formula I OG RI i ^' ^' (1), wherein: G is hydrogen or an agriculturally acceptable metal, sulfonium, ammonium or latentiating group; and R\ R^, R^, R"* and R^ are independently hydrogen, halogen, Ci-Cealkyl. Ci-CehaloalkyI, Cr Cealkoxy, Ci-Cehaloalkoxy, C2-C6alkenyl, C2-C6haloalkenyl, Cj-Cealkynyl, Ca-Cealkenyloxy, Ca-Cehaloalkenyloxy, Ca-Cealkynyioxy, Ca-CecycloalkyI, Ci-Cealkylthio. Ci-Cealkylsulfinyl, Ci- Cealkylsulfonyl, Ci-Cehaloalkylsulfonyl, Ci-Cealkoxysulfonyl, Ci-Cehaloalkoxysulfonyl, cyano, nitro, phenyl, phenyl substituted by Ci-C4alkyl, d-Cahaloalkyl, Ci-Caalkoxy, Ci-Cahaioalkoxy, cyano, nitro, halogen, Ci-Caalkylthio, CrCsalkylsuifinyl or CrCaaikylsulfonyl, or heteroaryl or heteroaryl substituted by Ci-C4alkyl, C-CshaloalkyI, Ci-C3alkoxy, Ci-Cahaloalkoxy, cyano, nitro, halogen, Ci-Caalkylthio, Ci-Caalkyisulfinyl or Ci-Caalkylsulfonyl, or benzyl or benzyl substituted by Ci-C4alkyl, Ci-Cshaloaikyl. Ci-Caalkoxy, d-Cshaloalkoxy, cyano, nitro, halogen, Ci-Caaikylthio, Ci-Caalkylsulfinyl or Ci-Caalkylsulfonyl, or Ca-CecycloalkylCi-CsalkyI in which a ring or chain methylene group is optionally replaced by an oxygen or sulfur atom; and/or R^ and R' or R" and R^ together with the carbon atoms to which they are attached form an optionally substituted 3- to 8-membered ring, optionally containing an oxygen, sulphur or nitrogen atom; and/or R^ and R" together form a bond; and Q is CS-CB saturated or mono-unsaturated heterocyclyl containing at least one heteroatom selected from O, N and S, unsubstituted or substituted by a residue of formula =0, =N-R^°, Ci-C4alkyl. Ci-C4haloalkyl, Ci-C4alkoxyC,-C2alkyl, Cs-Cecycloalkyi, phenyl or phenyl substituted by C,-C4alkyl, Ci-CahaloalkyI, Ci-Caalkoxy, Ci-Cahaloalkoxy, cyano, nitro, halogen, Ci-Caalkylthio. Ci-Caalkyisulfinyl or Ci-Caalkylsulfonyl, where R^° is Ci-Cealkyi, Ci- 151- Cghaloalkyl. Ca-Crcycloalkyl, Ci-Ceslkoxy. Ci-Cehaloalkoxy, Ci-Cealkylsulfinyl, Ci- Ceslkylsulfonyl, d-Cealkylcarbonyl, Ci-Cehaloalkylcarbonyl, Ci-Cealkoxycarbonyl. Cr Cealkylaminocarbonyl, C2-C8dialkylaminocarbonyl, C-Cehaloalkylsulfinyl or Ci- Cehaloalkylsulfonyl; or Q is an heteroaryl or heteroaryl substituted by Ci-C4alkyl, Ci-CahaloalkyI, Ci-Csalkoxy, Ci- Cahaloalkoxy, cyano. nitro, halogen, Ci-Caalkylthio, Ci-Caalkylsulfinyl or Ci-Caalkylsulfonyl; and m is 1, 2 or 3; and Het is an optionally substituted monocyclic or bicyclic heteroaromatic ring; wherein, in the optionally substituted monocyclic or bicyclic heteroaromatic ring which is Het, the optional substituents are selected, independently, from halogen, nitro, cyano, rhodano, isothiocyanato, Ci-CealkyI, Ci-Cehaloaikyl, Ci-C6alkoxy(Ci-C6)alkyl, Ca-Cealkenyl, C2- Cehaioalkenyl, C2-C6alkynyl, Ca-Cycycloalkyi (itself optionally substituted with Ci-CealkyI or halogen), Cs-ycycloalkenyl (itself optionally substituted with Ci-CealkyI or halogen), hydroxy, Ci-Cioalkoxy, Ci-Cioalkoxy(C,-Cio)alkoxy, tri(Ci-C4)alkylsilyl(Ci-C6)alkoxy, Ci- C6alkoxycarbonyl(Ci-Cio)alkoxy, Ci-Ciohaloalkoxy, aryl(Ci-C4)alkoxy (where the aryl group is optionally substituted with halogen or Ci-CealkyI), Cs-C/Cycloalkyloxy (where the cycloalkyi group is optionally substituted with Ci-CealkyI or halogen), Ca-Cioalkenyloxy, C3- Cioalkynyloxy, mercapto, Ci-Cioalkylthio, Ci-Ciohaloalkylthio, aryl(Ci-C4)alkylthio, C3- Cycycloalkyithio (where the cycloalkyi group is optionally substituted with Ci-Cgalkyi or halogen), tri(Ci-C4)-alkylsilyl(Ci-C6)alkylthio, arylthio, Ci-Cealkylsulfonyl, C^- Cehaloalkylsulfonyl, Ci-Cealkylsulfinyl, Ci-Cehaloalkylsulfinyl, arylsulfonyl, tri(Ci-C4)alkylsilyl, aryldi(Ci-C4)alkylsilyl, Ci-C4alkyldiarylsilyl, triarylsilyl, Ci-Cioalkylcarbonyl, HO2C. Cr Cioalkoxycarbonyl, aminocarbonyl, Ci-Cealkylaminocarbonyl, di(Ci-C6alkyl)-aminocarbonyl, N-(CrC3 alkyl)-A/-(Ci-C3alkoxy)aminocarbonyl, d-Cealkylcarbonyloxy, arylcarbonyloxy, di(Ci-C6)alkylaminocarbonyloxy, aryl (itself optionally substituted with Ci-CealkyI or halogen), heteroaryl (itself optionally substituted with Ci-CealkyI or halogen), heterocyclyl (itself optionally substituted with Ci-CealkyI or halogen), aryloxy (where the aryl group is optionally substituted with Ci-CealkyI or halogen), heteroaryloxy (where the heteroaryl group is optionally substituted with Ci-CealkyI or halogen), heterocyclyloxy (where the heterocyclyl group is optionally substituted with Ci-CealkyI or halogen), amino, d-Cealkylamino, di(Ci- C6)alkylamino, Ci-Ceaikylcarbonylamino, /V-(Ci-C6)alkylcarbonyl-/S/-(CrC6)alkylamino, and arylcarbonyl (where the aryl group is itself optionally substituted with halogen or Ci-CealkyI); -152- or two adjacent positions on ihe Het heteroaromatic system are optionally cyclised to form a 5, 6 or 7 membered carbocyclic or heterocyclic ring, itself optionally substituted with halogen or CrCealkyI; or, in the optionally substituted monocyclic or bicyclic heteroaromatic ring which is Het, the optional substituents are selected from arylcarbonylamino (where the aryl group is substituted by Ci-CealkyI or halogen), (CrC6)alkoxycarbonylamino, (Ci- C6)alkoxycarbonyl-A/-(Ci-C6)alkylamino, aryloxycarbonylamino (where the aryl group is substituted by Ci-CealkyI or halogen), aryloxycarbonyl-A/-(Ci-C6)alkylamino, (where the aryl group is substituted by Ci-CealkyI or halogen), arylsulphonylamino (where the aryl group is substituted by Ci-CealkyI or halogen), arylsulphonyl-A/-(Ci-C6)alkylamino (where the aryl group is substituted by Ci-CealkyI or halogen), aryl-N-(Ci-C6)alkylamino (where the aryl group is substituted by Ci-CgalkyI or halogen), arylamino (where the aryl group is substituted by Ci-CealkyI or halogen), heteroaryl amino (where the heteroaryl group is substituted by C,- Cealkyl or halogen), heterocyclylamino (where the heterocyclyl group is substituted by Ci- Cealkyl or halogen), aminocarbonylamino, Ci-Cealkylaminocarbonylamino, di(Ci- C6)alkylaminocarbonylamino, arylaminocarbonylamino (where the aryl group is substituted by Ci-CealkyI or halogen), aryl-A/- (Ci-C6)alkylaminocarbonylamino (where the aryl group is substituted by Ci-CealkyI or halogen), Ci-C6alkylaminocarbonyl-A/-(Ci-C6)alkylamino, di(Ci- C6)alkylaminocarbonyl-A/-( Ci-C6)alkylamino, arylaminocarbonyl-A/-(Ci-C6)alkylamino (where the aryl group is substituted by Ci-CealkyI or halogen), and aryl-A/-(Ci-C6)alkylaminocarbonyl- /V-(Ci-C6)alkylamino (where the aryl group is substituted by Ci-Cgalkyl or halogen); and wherein, when R^ and R^ or R^ and R^ together with the carbon atoms to which they are attached form an optionally substituted 3- to 8-membered ring, optionally containing an oxygen, sulphur or nitrogen atom, then: when R^ and R^ or R^ and R' together with the carbon atoms to which they are attached form a carbocycle, then the optional substituents on the carbocycle are selected, independently, from halogen, nitro, cyano, rhodano, isothiocyanato, Ci-CealkyI, Ci- Cehaloalkyl, Ci-C6alkoxy(Ci-C6)alkyl, Cz-Cgalkenyl, Cz-Cehaloalkenyl, Ca-Cealkynyl, C3- Cycycloalkyl (itself optionally substituted with Ci-CealkyI or halogen), Cs-ycycloalkenyl (itself optionally substituted with Ci-CealkyI or halogen), hydroxy, Ci-Cioalkoxy, Ci-Cioalkoxy(Ci- C,o)alkoxy, tri(Ci-C4)alkylsilyl(Ci-C6)alkoxy, Ci-C6alkoxycarbonyl(Ci-Cio)alkoxy, Ci- Ciohaloalkoxy, aryl(Ci-C4)alkoxy (where the aryl group is optionally substituted with halogen or Ci-CealkyI), Ca-C/cycloalkyloxy (where the cycloalkyi group is optionally substituted with Ci-CealkyI or halogen), Ca-Cioalkenyloxy, C3-Cioalkynyloxy, mercapto, Ci-Cioalkylthio, Ci- 153- Ciohaloalkylthio, aryl(Ci-C4)alkylthio, Ca-Cycycloalkylthio (where the cycloalkyi group is optionally substituted with Ci-Cgalkyl or halogen), tri(Ci-C4)-alkylsilyl(Ci-C6)alkylthio, arylthio, Ci-Cealkyisulfonyl, Ci-Cehaloalkylsuifonyl, Ci-Cealkylsulfinyi, Ci-Cehaloalkylsulfinyl, arylsulfonyl, tri(Ci-C4)alkylsilyl, aryldi(Ci-C4)alkylsilyl. Ci-C4alkyldiarylsilyl, triarylsilyl. C,- Cioalkylcarbonyl, HO2C, Ci-Cioalkoxycarbonyl, aminocarbonyl, Ci-Cealkylaminocarbonyl, di(Ci-C6alkyl)-aminocarbonyl, /\/-(Ci-C3 alkyl)-A/-(Ci-C3alkoxy)anninocarbonyl, d - Cealkylcarbonyloxy, arylcarbonyloxy, di(CrC6)aikylaminocarbonyloxy, aryl (itself optionally substituted with Ci-CealkyI or halogen), heteroaryl (itself optionally substituted with Ci-CealkyI or halogen), heterocyclyl (itself optionally substituted with Ci-CealkyI or halogen), aryloxy (where the aryl group is optionally substituted with Ci-CealkyI or halogen), heteroarytoxy (where the heteroaryl group is optionally substituted with Ci-CealkyI or halogen), heterocyclyloxy (where the heterocyclyl group is optionally substituted with Ci-CealkyI or halogen), amino, d-Cealkylamino, di(Ci-C6)alkyiamino, Ci-Cealkylcarbonylamino, A/-(Ci- C6)alkylcarbonyl-A/-(Ci-C6)alkylamino, and arylcarbonyl (where the aryl group is itself optionally substituted with halogen or Ci-CealkyI); and when R^ and R^ or R^ and R^ together with the carbon atoms to which they are attached form an optionally substituted 3- to 8-memt)ered ring which contains an oxygen, sulphur or nitrogen atom, then, in the resulting heterocyclyl group, the one or more optional substituents are independently selected from halogen, Ci-CealkyI, Ci-Cehaloalkyi, d - Cealkoxy, Ci-Cehaloalkoxy, Ci-Cealkylthio, Ci-Cealkylsulfinyl, Ci-Cealkylsulfonyl, nitro and cyano; and wherein the latentiating group G is selected from the groups CrCsalkyI, C2-C8haloalkyl, phenylCi-CsalkyI (wherein the phenyl is optionally substituted by Ci-CaalkyI, Ci-CahaloalkyI, Ci-Caalkoxy, Ci-Cahaloalkoxy, Ci-Caalkylthio, Ci-Caalkylsulfinyl, Ci-Caalkylsulfonyl, halogen, cyano or by nitro), heteroarylCi-Caalkyi (wherein the heteroaryl is optionally substituted by Ci-C3alkyl, Ci-CahaloalkyI, Ci-Caalkoxy, Ci-Cahaloalkoxy. Ci-Csalkylthio, Ci-Caalkylsulfinyl, C1-C3 alkylsulfonyl, halogen, cyano or by nitro), Cs-Caalkenyl, Ca-Cehaloalkenyl, Cs-Csalkynyl, C(X^)-R^ C(X'')-X'=-R^ C(X'')-N(R=)-R^ -S02-R^ -P(X^)(R')-R9 and CHz-X'-R*'; wherein X^, X^ X"", X'', X* and X' are independently of each other oxygen or sulfur; and wherein R^ is H. Ci-CiaalkyI, Ca-Ciealkenyi, Cz-Cisalkynyl, Ci-Ciohaloalkyl, Ci- Ciocyanoalkyl, Ci-C,onitroalkyl, Ci-Cioaminoalkyl, Ci-C5alkylamino(Ci-C5)alkyl, C2- C8dialkylamino(Ci-C5)alkyl, C3-C7Cycloalkyl(Ci-C5)alkyl, Ci-C5alkoxy(Ci-C5)alkyl, C3- -154- C5alkenyloxy(Ci-C5)alkyl, Ci-C5alkylthio(Ci-C5)alkyl, CrC5alkylsulfinyl(Ci-C5)alkyl, d - C5alkylsulfonyl(Ci-C5)alkyl, C2-C8alkylideneaminoxy(Ci-C5)alkyl, Ci-CsalkylcarbonyKCi- C5)alkyl, Ci-C5alkoxycarbonyl(Ci-C5)alkyl, aminocarbonyl(Ci-C5)alkyl, C,- C5alkylaminocarbonyl(Ci-C5)alkyl. C2-C8dialkylaminocarbonyl(Ci-C5)alkyl, Ci- C5alkylcarbonylamino(CrC5)alkyl, A/-(Ci-C5)alkylcarbonyl-A/-(Ci-C5)alkylamino(Ci-C5)alkyl, C3-C6trialkylsilyl(Ct-C5)alkyl, phenyl(Ci-C5)alkyl (wherein the phenyl is optionally substituted by Ci-Csalkyl. Ci-Cahaioalkyl. CrCaalkoxy, Ci-Cahaloalkoxy, Ci-Caalkylthio, Ci- Caalkylsulfinyl, Ci-Caalkylsulfonyi, halogen, cyano, or by nitro), heteroaryl(Ci-C5)alkyl (wherein the heteroaryl is optionally substituted by Ci-CsalkyI, Ci-CahaloalkyI, Ci-Caalkoxy, Ci-Cahaloaikoxy, Ci-Caalkylthio, Ci-Caaikylsulfinyi, Ci-Caalkylsulfonyl, halogen, cyano, or by nitro), Cj-Cshaloalkenyl, Ca-CgCycloalkyI, or phenyl or phenyl substituted by Ci-Caaikyl, Ci- Cahaloalkyl, Ci-Caalkoxy, Ci-Cahaloalkoxy, halogen, cyano or nitro, or heteroaryl or heteroaryl substituted by Ct-Ca alkyl, Ci-CahaloalkyI, Ci-Caalkoxy, Ci-Cahaloalkoxy, halogen, cyano or nitro; R" is Ci-CisalkyI, Cs-Ciaalkenyl, Ca-Ciealkynyl. Cz-CiohaloalkyI, Ci-Ciocyanoalkyl, C,- Cionitroalkyl, Cz-CioaminoaikyI, Ci-C5alkylamino(Ci-C5)alkyl, C2-C8dialkylamino(Ci-C5)alkyl, C3-C7cycloalkyl(Ci-C5)alkyl, Ci-C5alkoxy(Ci-C5)alkyl, C3-C5alkenyloxy(Ci-C5)alkyl, C3- C5alkynyloxy(Ci-C5)alkyl, CrC5alkylthio(Ci-Cs)alkyl, Ci-C5alkylsulfinyl(Ci-C5)alkyl, C,- C5alkylsulfonyl(Ci-C5)alkyl, C2-Cealkylideneaminoxy(Ci-C5)alkyl. Ci-CsaikylcarbonyKCr C5)alkyl, Ci-C5aikoxycarbonyi(Ci-C6)alkyl, aminocart)onyl(Ci-C5)aikyl, C,- C5alkylanriinocarbonyl(Ci-C5)alkyl, C2-C8dialkylaminocarbonyl(Ci-C5)alkyl. Ci- C5alkylcarbonylamino(Ci-C5)alkyl, A/-(Ci-C5)alkylcarbonyl-A/.(Ci-C5)alkylamino(Ci-C5)alkyl, C3-C6trialkylsilyl(Ci-C5)alkyl, phenyl(Ci-C5)alkyl (wherein the phenyl is optionally substituted by Ci-CaalkyI, Ci-CahaloalkyI, CrCaalkoxy, Ci-Cahaloalkoxy, Ci-Caalkylthio, Cr Csalkylsulfinyl, Ci-Caalkyisulfonyl, halogen, cyano, or by nitro), heteroarylCi-Csalkyi, (wherein the heteroaryl is optionally substituted by CrC3alkyl, Ci-C3haloalkyl, Ci-Caalkoxy, Cr C3haloalkoxy, Ci-Csalkyl-thio, Ci-Csalkylsulfinyl, Ci-C3alkylsulfonyl, halogen, cyano. or by nitro), C3-C5haloalkenyl. Cs-Cscycloalkyi, or phenyl or phenyl substituted by Ci-Csalkyl. Ci- Cshaloalkyl. Ci-Csalkoxy, Ci-C3haloalkoxy, halogen, cyano or nitro, or heteroaryl or heteroaryl substituted by C1-C3 alkyl, Ci-C3haloalkyl, CrCaalkoxy, Ci-Cahaloalkoxy. halogen, cyano or nitro; R"" and R*" are each independently of each other hydrogen, Ci-CioalkyI, C3-Cioalkenyl, C3- Cioalkynyl, C2-Ciohaloalkyl. Ci-Ciocyanoalkyl, Ci-Cionitroalkyl. Ci-CioaminoalkyI, C,- -155- C5alkylamino(Ci-C5)alkyl, C2-C8dialkylamino(Ci-C5)alkyl, C3-C7cycloalkyl(Ci-C5)alkyl. C,- C5alkoxy(Ci-C5)alkyl, C3-C5alkenyloxy(Ci-C5)alkyl. C3-C5alkynyloxy(Ci-C5)alkyl, Ci- C5alkylthio(Ci-C5)alkyl. Ci-C5alkylsulfinyl(Ci-C5)alkyl, Ci-C5alkylsulfonyl(Ci-C5)alkyl, Cg- C8alkylideneaminoxy(Ci-C5)alkyl, Ci-C5alkylcarbonyl(Ci-C5)alkyl, Ci-C5alkoxycarbonyl(Ci- C5)alkyl, aminocarbonyl(Ci-C5)alkyl, Ci-C5alkylaminocarbonyl(Ci-C5)alkyl, C2- C8dialkylaminocarbonyl{Ci-C5)alkyl, Ci-C5alkylcarbonylamino(Ci-C5)alkyl, A/-(C,- C5)alkylcarbonyl-A/-(C2-C5)alkylaminoalkyl, C3-C6trialkylsilyl(Ci-C5)alkyl, phenyl(Ci-C5)alkyl {wherein the phenyl is optionally substituted by Ci-CaalkyI, Ci-Cahaloalkyl. Ci-Caalkoxy, Ci- C3haloalkoxy, Ci-C3alkylthio, Ci-Caalkylsulfinyl, CrC3alkylsulfonyl. halogen, cyano. or by nitro), heteroaryl(Ci-C5)alkyl (wherein the heteroaryl is optionally substituted by Ci-CaalkyI, Ci-CahaloalkyI, Ci-Caalkoxy, Ci-Cshaloalkoxy, d-Csalkylthio, Ci-Csalkylsulfinyl, Ci- C3alkylsulfonyl, halogen, cyano, or by nitro). Cj-Cshaloalkenyl, Cs-Cscycioalkyl, or phenyl or phenyl substituted by Ci-CsalkyI, Ci-CahaloalkyI, Ci-Caalkoxy. d-Cahaloalkoxy, halogen, cyano or nitro, or heteroaryl or heteroaryl substituted by Ci-CaaikyI, Ci-CahaloalkyI, Ci- C3alkoxy, Ci-Cahaloalkoxy, halogen, cyano or nitro, or heteroarylamino or heteroarylamino substituted by Ci-C3alkyl, d-Cahaloalkyl, Ci-Csalkoxy, Ci-Cshaloalkoxy, halogen, cyano or nitro, or diheteroarylamino or diheteroarylamino substituted by Ci-C3alkyl, Ci-CahaloalkyI, Cr Csalkoxy, Ci-Cahaloalkoxy, halogen, cyano or nitro, or phenylamino or phenylamino substituted by Ci-CsalkyI, Ci-CshaloalkyI, Ci-Csalkoxy, CrCshaloalkoxy, halogen, cyano or by nitro, or diphenylamino or diphenylamino substituted by Ci-CaalkyI, Ci-CshaloalkyI, Ci- Csalkoxy, Ci-Cshaloalkoxy, halogen, cyano or by nitro, or Cs-CTcycloalkylamino, di-C3- C/cycloalkylamino or Ca-Crcycloalkoxy; or fC^ and R" join together to form a 3-7 membered ring, optionally containing one heteroatom selected from O or S; R* is Ci-Cioalkyl. Ca-Cioalkenyl, Cz-Cioalkynyl, Ci-CiohaloalkyI, Ci-CiocyanoalkyI, Ci- Cionitroalkyl, Ci-Cioaminoalkyl, Ci-C5alkylamino(Ci-C5)alkyl, C2-C8dialkylamino(Ci-C5)alkyl, C3-C7cycloalkyl(C,-C5)alkyl, Ci-C5alkoxy(Ci-C5)alkyl, C3-C5alkenyloxy(Ci-C5)alkyl, C3- C5alkynyloxy(Ci-C5)alkyl. Ci-C5alkylthio(Ci-C5)alkyl, Ci-C5alkylsulfinyl(Ci-C5)alkyl, Ci- C6alkylsulfonyl(Ci-C5)alkyl, C2-C8alkylideneaminoxy(Ci-C5)alkyl, Ci-CsalkylcarbonyKCr C5)alkyl. Ci-C5alkoxycarbonyl(Ci-C5)alkyl, aminocarbonyl(Ci-C5)alkyl, Ci- C5alkylaminocarbonyl(Ci-C5)alkyl, C2-C8dialkylaminocarbonyl(Ci-C5)alkyl, Ci- C5alkylcarbonylamino(Ci-C5)alkyl, A/-(Ci-C5)alkylcarbonyl-A/-(Ci-C5)alkylamino(Ci-C5)alkyl, C3-C6trialkyisilyl(Ci-C5)aikyl, phenyl(Ci-C5)alkyl (wherein the phenyl is optionally substituted by Ci-Caalkyi, Ci-Cshaloalkyl. Ci-C3alkoxy, Ci-Cahaloalkoxy, CrCsalkylthio, Ci- 156- Caalkylsulfinyl, Ci-Caalkylsulfonyl, halogen, cyano, or by nitro), heteroaryl(Ci-C5)alkyl (wherein the heteroaryl is optionally substituted by C-CsalkyI, Ci-CahaloalkyI, Ci-Caalkoxy. Ci-Cahaloalkoxy, Ci-Caalkylthio, Ci-Caalkylsulfinyl, Ci-Caalkylsulfonyl, halogen, cyano, or by nitro), Ca-Cshaloalkenyl, Ca-CscycloalkyI, or phenyl or phenyl substituted by Ci-CaalkyI, Ci- Cahaloalkyl, C,-C3alkoxy, Ci-Cshaloalkoxy, halogen, cyano or nitro, or heteroaryl or heteroaryl substituted by d-Caalkyl, Ci-CahaloalkyI, Ci-Caalkoxy, Ci-Cahaloalkoxy, halogen, cyano or by nitro, or heteroarylamino or heteroarylamino substituted by C1-C3 alkyl, Ci- Cahaloalkyl, Ci-Csalkoxy, Ci-Cahaloalkoxy, halogen, cyano or by nitro, or diheteroarylamino or diheteroarylamino substituted by Ci-CsalkyI, Ci-CahaloalkyI, Ci-Caaikoxy, Ci-Cahaloalkoxy. halogen, cyano or nitro, or phenylamino or phenylamino substituted by CrCaalkyI, Ci- Cahaioalkyl, Ci-Caalkoxy, Ci-Cahaloalkoxy, halogen, cyano or nitro, or diphenylamino or diphenylamino substituted by Ci-CaalkyI, Ci-CahaloalkyI, CrCaalkoxy, Ci-Cshaloalkoxy, halogen, cyano or nitro, or Ca-C/cycloalkylamino, diCa-Crcycloalkylamino, Cs-Crcycloalkoxy, Ci-Cioalkoxy, CrCiohaloalkoxy, Ci-Csalkyiamino or C2-C8dialkylamino; R* and R^ are are each independently of each other Ci-Cioalkyl, Ca-Cioalkenyl, Ca-Cioalkynyl, Ci-Cioalkoxy, Ci-Ciohaloalkyl, Ci-CiocyanoalkyI, Ci-Cionitroaikyl. CrCioaminoalkyl. Ci- C5alkylamino(Ci-C5)alkyl, C2-C8dialkylamino(Ci-C5)alkyl, C3-C7cycloalkyl(Ci-C5)alkyl. C,- C5alkoxy(C,-C5)alkyl, C3-C5alkenyloxy(C,-C5)alkyl, C3-C5alkynyioxy(Ci-C5)alkyl. C,- C5alkylthio(CrC5)alkyl, Ci-C5alkylsulfinyl(Ci-C5)alkyl, Ci-C5alkylsulfonyl(Ci-C5)alkyl, C2- C8alkylideneaminoxy(Ci-C5)alkyl, Ci-C5alkylcarbonyl(Ci-C5)alkyl, Ci-C5alkoxycarbonyl(Ci- C5)alkyl, aminocarbonyl(Ci-C5)aikyl, Ci-C5alkyiaminocarbonyl(Ci-C5)alkyl, C2- C8dialkylaminocarbonyl(Ci-C5)alkyl, Ci-C5alkylcarbonylamino(Ci-C5)alkyl, A/-(Ci- C5)alkylcarbonyl-/V-(C2-C5)alkylaminoalkyl, C3-C6trialkylsilyl(Ci-C5)alkyl, phenyl(C,-C5)alkyl (wherein the phenyl is optionally substituted by Ci-CsalkyI, Ci-CshaloalkyI, Ci-C3alkoxy, Ci- Cshaloalkoxy, d-Csalkylthio, Ci-Csalkylsulfinyl, Ci-C3alkylsuifonyl, halogen, cyano, or by nitro), heteroaryl(Ci-C5)alkyl (wherein the heteroaryl is optionally substituted by Ci-CsalkyI, Ci-C3haloalkyl, Ci-Cgalkoxy, Ci-Cshaloalkoxy, Ci-C3alkylthio, Ci-Csalkylsulfinyl, Ci- Csalkylsulfonyl, halogen, cyano, or by nitro), C2-C5haloalkenyl, C3-C8cycloalkyl, or phenyl or phenyl substituted by Ci-C3alkyl, Ci-C3haloalkyl, Ci-Csalkoxy. Ci-Cshaloalkoxy, halogen, cyano or nitro, or heteroaryl or heteroaryl substituted by C1-C3 alkyl, Ci-C3haloalkyl, Ci- Csalkoxy, Ci-Cshaloalkoxy, halogen, cyano or by nitro, or heteroarylamino or heteroarylamino substituted by C1-C3 alkyl, Ci-CshaloalkyI, Ci-C3alkoxy, Ci-Cshaloalkoxy, halogen, cyano or by nitro, or diheteroarylamino or diheteroarylamino substituted by C1-C3 alkyl, Ci-C3haloalkyl, Ci-C3alkoxy, Ci-Cshaloalkoxy, halogen, cyano or nitro, or phenylamino -157- or phenylamino substituted by CrCaalkyI, Ci-CahaloalkyI, Ci-Csalkoxy, C-Cahaloalkoxy. halogen, cyano or nitro, or diphenylamino or diphenylamino substituted by Ci-CaalkyI, d - Cshaioalkyl, CrCaaikoxy. Ci-Cahaloalkoxy. halogen, cyano or nitro, or Ca-Cycycloalkylamino. diCs-C/cycloalkylamino. Ca-C/cycloalkoxy, Ci-Ciohaloalkoxy, Ci-Csalkylamino or C2- Csdialkylamino, or benzyloxy or phenoxy, wherein the benzyl and phenyl groups are in turn optionally substituted by Ci-CsalkyI, Ci-CahaloalkyI, Ci-Caalkoxy. Ci-Cahaloalkoxy, halogen, cyano or nitro; and R" is Ci-CioalkyI, Ca-Cioalkenyl. Cs-Cioalkynyl, Ci-CiohaloalkyI, Ci-Ciocyanoalkyl, Ci- Cionitroalkyl, CrCioaminoalkyI, Ci-C5alkylamino(Ci-C5)alkyl, C2-C8dialkylamino(CrC5)alkyl, C3-C7Cycloalkyl(Ci-C5)alkyl, Ci-C5alkoxy(Ci-C5)alkyl, C3-C5alkenyloxy(Ci-C5)alkyl, C3- C5alkynyloxy(C,-C5)alkyl, Ci-C5alkylthio(Ci-C5)alkyl, Ci-C5alkylsulfinyl(C,-C5)alkyl. C,- C5alkylsulfonyl(Ci-C5)alkyl, C2-C8alkylideneaminoxy(Ci-C5)alkyl, Ci-C5alkylcarbonyl(Ci- C5)alkyl, Ci-C5alkoxycarbonyl(Ci-C5)alkyl, anninocarbonyl(Ci-C5)alkyl, C^- C5alkylaminocarbonyl(Ci-C5)alkyl, C2-C6dialkylaminocarbonyl{Ci-C5)alkyi, Ci- C5alkylcarbonylamino(Ci-C5)alkyl, A/-(C,-C5)alkylcarbonyl-A/-(Ci-C5)alkylamino(Ci-C5)alkyl, C3-C6trialkylsilyl(Ci-C5)alkyl, phenyl(Ci-C5)alkyl (wherein wherein the phenyl is optionally substituted by C,-C3alkyl, Ci-Cshaloaikyl, Ci-C3alkoxy, Ci-Cahaloalkoxy, Ci-Csalkylthio, Ci- C3alkylsulfinyl, C1-C3 alkylsulfonyl, halogen, cyano or by nitro), heteroaryl(Ci-C5)alkyl (wherein the heteroaryl is optionally substituted by Ci-C3alkyl, Ci-C3haloalkyl, Ci-Csalkoxy, Ci-Cshaloalkoxy, Ci-Csalkylthio, CrCsalkylsulfinyl, C1-C3 alkylsulfonyl, halogen, cyano or by nitro), phenoxy(Ci-C5)alkyl (wherein the phenyl is optionally substituted by Ci-CsalkyI, C,- Cshaloalkyi, Ci-Csalkoxy, Ci-Cahaloalkoxy, Ci-Csalkylthio, Ci-Caalkylsulfinyl, C1-C3 alkylsulfonyl, halogen, cyano or by nitro), heteroaryloxy(Ci-C5)alkyl (wherein the heteroaryl is optionally substituted by Ci-CsalkyI, Ci-CshaloalkyI, Ci-Csalkoxy, Ci-Cshaloalkoxy, Ci- C3alkylthio, Ci-C3alkylsulfinyl, C1-C3 alkylsulfonyl, halogen, cyano or by nitro), C3- Cshaioalkenyl, C3-C8Cycloalkyl, or phenyl or phenyl substituted by Ci-CsalkyI, CrCshaloalkyI, Ci-Csalkoxy, Ci-Cshaloalkoxy, halogen or by nitro, or heteroaryl or heteroaryl substituted by Ci-CsalkyI, Ci-C3haloalkyl, Ci-Caalkoxy, Ci-Cahaloalkoxy, halogen, cyano or by nitro; and wherein the compound is optionally an agronomically acceptable salt thereof. 2. A compound according to claim 1, wherein R^ is hydrogen, halogen, Ci-CealkyI, Ci- Cghaloaikyl, Ci-Cealkoxy or Ci-Cehaloalkoxy. -158- 3. A compound according to claim 2, wherein R^ is hydrogen or methyl. 4. A compound according to claim 1, wherein R^and R^ independently are hydrogen, halogen, Ci-CealkyI, Ci-CehaloalkyI, Ci-Cealkoxy or Ci-Cehaloalkoxy. 5. A compound according to claim 1, 2, 3 or 4. wherein R^and R^ independently are hydrogen, halogen, Ci-CealkyI, Ci-Cehaloalkyl. Ci-Ceaikoxy or Ci-Cehaloalkoxy. 6. A compound according to claim 5, wherein R" and R^ independently are hydrogen or methyl. 7. A compound according to any one of claims 1 to 6, wherein m is 1. 8. A compound according to any one of claims 1 to 7, wherein Q is a group selected from fomiulae Qi to Q107 as defined b)elow: <«)«-"-QL, Q, Q2 Q3 Q^ Q, ^^^""Ox <'^""OL ^'^"'^0"'' ^'^""^'' ^^'"-^^ -^^' -"-iy^ -.-fr' ...-^^ ""'-€X, '^'"-d, '"'""Ci, "".-^r' Q2, QjZ Q23 °'' Q25 -159- <«.* '"W^ '^'r) A A N=^ N-O N=/Q4S Q47 Q^g Q« Q50 'V "C^- \ > ~-^i' Q5I Q52 Q53 Q^ Q^ (Rj/o-^ (R)„/^ '^^"O^ ^^"X^ (R)n^S-^ Q56 Q57 Q« Q59 Qeo o 0 0 0 0 S'^-N''^ _ir^N'* ^ \ ' ' N-^N'* R-N'^N-'^ ,,,XJ •"'••O '^''-O ,.,^" ^>-^ Qe, ^62 Q„ Qg, Qej o 0 0 0 0 R.^A^^A A-^ NA,^A ^A^.A ^A .A o Qee ^67 Qg, Qge Q70 -160- QTB Q77 Q^ Q„ Qgg 9 ^ ^^^"X\ /^ °^^ N=\ N=\ A ^^— A A A Qsa Q«5 Qgi Q82 QM <«)."-^' ^'^^--O^' ^"^""O^'' ^^^""i^' Q91 °'^ ^ 0 9 4 0 9 5 '-.-p^* -.-Xl, <"'"^, Q1OI Q,o2 Q,03 Q^^ Q^^ ' eX/>-^' A:>~r B^-z^^' Het, Hetg Hetj Het^ "^j" V<"' '-W ""v" .x^- .^r- .)^"-"" .X--" R Hetg Hetg Het7 Hetg Hetg Het,o Het,, Het^j wherein: B designates the point of attachment to the ketoenol moiety; W' is N or CR®; W^ and W^ are independently of each other N or CR^; W^ is N or CR^°; with the proviso that at least one of \N\ W^, W^ or W^ is N; X is O, S, or N R " ; Z is N or CR^^ wherein R® is halogen, Ci-CaalkyI, Ci-Cghaloalkyl, vinyl, ethynyl, or methoxy; R^ is phenyl, substituted once, twice or three times, by halogen, Ci-Ca alkyl, d-Ca alkoxy, CrC2 haloalkyi, C1-C2 haloalkoxy or cyano; R® is hydrogen, C1-C4 alkyl, Ca-Caalkenyl, Ca-Caalkynyl, CrC4 haloalkyi or C2-C3 haloalkenyl; -164- R^is hydrogen, methyl, halomethyl or halogen; R^° is hydrogen, halogen, Ci-C^ alkyl, C1-C4 haloalkyi, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C1-C4 alkoxy. C,-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl or cyano; R" is phenyl, substituted once, twice or three times, by halogen, C1-C2 alkyl, C1-C2 alkoxy. C1-C2 haloalkyi, C1-C2 haloalkoxy or cyano; R^^ is hydrogen, methyl, ethyl or halomethyl; and R" is hydrogen, methyl, ethyl, halomethyl. haloethyl, halogen, cyano or nitro. 15. A compound according to claim 14, wherein: R* is methyl or ethyl; R* is methyl or ethyl; R^ is hydrogen; and R^° is hydrogen, halogen, methyl or ethyl. 16. A compound according to any one of claims 1 to 15, wherein the latentiating group G is a group -C(X')-R' or -C(X'')-X'=-R^ 17. A compound according to any one of claims 1 to 15, wherein the latentiating group G is a group -C(X^)-R' or -C(X'')-X"'-R^ wherein R^ is hydrogen or Ci-Ci8alkyl. R" is CrCi8alkyl. and the meanings of X', X" and X*^ are as defined in claim 1. 18. A compound according to any one of claims 1 to 15, wherein G is hydrogen, an alkali metal or an alkaline earth metal. 19. A compound according to claim 1, wherein: R^ is hydrogen or methyl; R^and R^ independently are hydrogen or methyl; R''and R^ independently are hydrogen or methyl; and Q is pyridyl, pyrimidinyl. pyridazinyl, quinolinyl. isoquinolinyl. cinnolinyl. phthalazinyl, quinazolinyl or quinoxalinyl, where these rings are optionally substituted one or two times by fluoro. chloro. bromo. methyl, methoxy, cyano or trifluoromethyl; or Q is thienyl, furyl. oxazolyl, isoxazolyl. benzofuryl. thiazolyl. oxazolyl, isothiazolyl, benzothienyl, benzoisothienyl. benzothiazolyl. benzisothiazolyl, benzoxazolyl or -165- benzisoxazolyl, where these rings are optionally substituted one or two times by fluoro, chloro, bromo, methyl, methoxy, cyano or trifluoromethyl; and m is 1; Het is a group Heta Hetj wherein X is S, Z is N, R^ is methyl or ethyl, R^ is 4-chlorophenyl or 4-bromophenyl, and B designates the point of attachment to the keloenol moiety; and G is hydrogen, an alkali metal or an alkaline earth metal. 20. A compound according to claim 19, wherein R' to R* are hydrogen and G is hydrogen. 21. A compound according to claim 1, wherein R^ to R^ are hydrogen; G is hydrogen, an alkali or an alkaline earth metal; m is 1; and Q is group selected from formulae Qi to Q7 as defined below: -.-cr* -^--Cr' -.-^^ --