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(12) Patent Application Publication (10) Pub. No.: US 2015/0342185 A1 Mound Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2015/0342185 A1 Mound Et Al US 20150342185A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2015/0342185 A1 Mound et al. (43) Pub. Date: Dec. 3, 2015 (54) HERBICIDALLY ACTIVECYCLIC DIONE C07D 309/32 (2006.01) COMPOUNDS, ORDERIVATIVES C07D 213/50 (2006.01) THEREFOR, SUBSTITUTED BY A PHENYL (52) U.S. Cl. WHICH HAS ANALKYNYL-CONTAINING CPC .............. A0IN 43/16 (2013.01); C07D 309/32 SUBSTITUENT (2013.01); C07C 49/747 (2013.01); A0IN 35/06 (2013.01); C07D 309/06 (2013.01); (71) Applicant: Syngenta Limited, Guildford Surrey C07D 213/50 (2013.01); A0IN 43/40 (CH) (2013.01); C07D 311/96 (2013.01); C07C 321/20 (2013.01); C07C329/06 (2013.01); (72) Inventors: William Roderick Mound, Bracknell A0IN 47/06 (2013.01); C07C 2102/44 Berkshire (GB); James Nicholas Scutt, (2013.01) Bracknell Berkshire (GB); Mark Slater, Bracknell Berkshire (GB); Nigel James (57) ABSTRACT Willetts, Bracknell Berkshire (GB) The present invention relates to a compound of formula (I), (73) Assignee: Syngenta Limited, Guildford Surrey wherein: X is methyl orchlorine; R is methyl or chlorine; R. (CH) is hydrogen, methyl, ethyl, n-propyl, cyclopropyl, vinyl, ethynyl, fluorine, chlorine, bromine, C-Calkoxy, C-C- (21) Appl. No.: 14/653,674 fluoroalkoxy, C-Calkoxy-C-Calkoxy- O C fluoroalkoxy-C-Calkoxy-; and Y is O, S, S(O), S(O), (22) PCT Filed: Dec. 19, 2013 N(C-C alkyl), N(C-Calkoxy), C(O), CRR or CR'R''CR'R' ; and G, R, R, R and R are as (86). PCT No.: PCT/EP2013/077541 defined herein; wherein the compound of formula (I) is optionally present as an agrochemically acceptable salt S371 (c)(1), thereof. These compounds are suitable for use as herbicides. (2) Date: Jun. 18, 2015 The invention therefore also relates to a method of controlling (30) Foreign Application Priority Data weeds, especially grassy monocotyledonous weeds, in crops ofuseful plants, comprising applying a compound of formula Dec. 21, 2012 (GB) ................................... 1223429.0 (I), or a herbicidal composition comprising such a compound, May 31, 2013 (GB) ... ... 1309.728.2 to the plants or to the locus thereof. Dec. 4, 2013 (GB) ................................... 1321553.8 Publication Classification (I) (51) Int. Cl. AOIN 43/16 (2006.01) C07C 49/747 (2006.01) AOIN35/06 (2006.01) CO7D 309/06 (2006.01) AOIN 47/06 (2006.01) AOIN 43/40 (2006.01) CO7D 3II/96 (2006.01) C07C32L/20 (2006.01) C07C329/06 (2006.01) US 2015/0342185 A1 Dec. 3, 2015 HERBICIDALLY ACTIVE CYCLIC DONE 0009 Copending PCT application PCT/EP2012/074118, COMPOUNDS, ORDERIVATIVES filed on 30 Nov. 2012 and published on 6 Jun. 2013 as WO THEREFOR, SUBSTITUTED BY A PHENYL 2013/079672A1 (Syngenta Limited and Syngenta Participa WHICH HAS ANALKYNYL-CONTAINING tions AG) discloses that certain substituted spiroheterocyclic SUBSTITUENT pyrrolidine dione compounds, having an alkynyl-phenyl headgroup, have herbicidal properties. 0001. The present invention relates to herbicidally active cyclic diones, in particular pyrandione, thiopyrandione, (0010 Copending PCT application PCT/EP2012/074172, cyclohexanedione, alkanediyl-bridged cyclohexanedione, filed on 30 Nov. 2012 and published on 6 Jun. 2013 as WO cyclohexanetrione or cycloheptanedione compounds, or 2013/079708 A1 (Syngenta Limited and Syngenta Participa derivatives thereof (e.g. enol ketone tautomer derivatives tions AG) discloses cyclopentane-1,3-dione compounds and thereof), to processes for their preparation, to herbicidal com derivatives (e.g. fused and/or spirocyclic bicyclic derivatives) positions comprising those compounds, and to their use in thereof, which are substituted at the 2-position of the cyclo controlling weeds such as grassy monocotyledonous weeds, pentane-1,3-dione by a phenyl which itself is substituted at especially in crops of useful plants, or in inhibiting undesired the 4-position by (specifically) either prop-1-ynyl or chloro plant growth. In particular, the present invention relates to ethynyl, and derivatives of the enol ketone tautomer of such herbicidally active cyclic dione compounds, or derivatives cyclopentanediones, which have herbicidal activity and/or thereof (e.g. enol ketone tautomer derivatives thereof), which plant-growth-inhibiting properties, especially in the control are substituted by a phenyl which has an alkynyl-containing of grassy monocotyledonous weeds and/or when used post substituent. emergence. 0002 WO 01/17972 A2 (Syngenta Participations AG) dis 0011 Cyclic dione compounds have now been found, in closes phenyl-substituted (such as 4-methyl-2,6-diethyl-phe particular pyran-3,5-dione, thiopyran-3,5-dione, cyclohex nyl-substituted) heterocycles suitable for use as herbicides. ane-1,3-dione, alkanediyl-bridged cyclohexane-1,3-dione, 0003 WO 03/013249 A1 (Bayer AG) and its equivalent cyclohexane-1,3,5-trione or cycloheptane-1,3-dione com US 2005/0054535A1 disclose selective herbicidal composi pounds, which are Substituted, at the ring-carbon atom of the tions comprising (a) a (Substituted-phenyl)-substituted cyclic cyclic dione which is between the two oxo-substituted ring ketoenol and (b) a compound which improves crop plant carbons of the cyclic dione, by a phenyl which itself is sub compatibility, in particular cloquintocet-mexyl or mefenpyr stituted at the 4-position by (specifically) either prop-1-ynyl diethyl. or chloroethynyl and at the 2-position by (specifically)methyl 0004 WO 2007/068427 A2 (Bayer CropScience AG) and or chlorine, or derivatives of the enol ketone tautomer of such its equivalent US 2009/0227563 A1 disclose a composition cyclic diones, which have herbicidal activity and/or plant comprising (a) a (Substituted-phenyl)-substituted cyclic growth-inhibiting properties, in particular in the control of ketoenol as a herbicide, and (b) an ammonium or phospho grassy monocotyledonous weeds. The herbicidal data avail nium salt to boost activity. able, as shown in the Biological Examples hereinafter, Sug 0005 WO 2008/071405 A1 and WO 2009/074314 A1 gests that these 4-(prop-1-ynyl)-2-(methyl or chloro)-phenyl (both Syngenta Limited and Syngenta Participations AG) or 4-(chloroethynyl)-2-(methyl or chloro)-phenyl cyclic each disclose herbicidally active pyran-3,5-diones, thiopy dione compounds are more potent herbicides against grassy ran-3,5-diones and cyclohexane-1,3,5-triones, each Substi monocotyledonous weeds (e.g. when applied post-emer tuted at the 4-position of the cyclic dione or trione by an gence) than the corresponding 4-ethynyl-2-(methyl or aryl-substituted-phenyl or by a heteroaryl-substituted-phe chloro)-phenyl cyclic dione compounds. The herbicidal nyl. activity against 'warm-season’ (warm climate) grassy mono 0006 WO 2010/081755 A1 and WO 2010/0892 11 A1 cotyledonous weeds of most of the compounds of the inven (both Syngenta Limited) each disclose herbicidally active tion which have been exemplified and tested herein (com pyran-3,5-diones, thiopyran-3,5-diones, cyclohexanediones, pounds A-1 to A-17, A-18 to A-24, P-1 to P-5, or P-7) appears cycloheptanediones and cyclohexanetriones, each Substi to be potent, in particular after post-emergence application of tuted by an aryloxy-substituted-phenyl or by a heteroaryloxy the compounds at an application rate of about 250 g/ha. Also, substituted-phenyl. many of the exemplified compounds exhibit areasonably low 0007 WO 2008/110308A1 (Syngenta Participations AG) phytotoxicity against wheat and/or certain docotyledonous discloses 2-(Substituted-phenyl)-cyclohexane-1,3-dione crops, in particular soybean and/or Sugar beet (see Biological compounds and derivatives, containing a R X (CRR) Examples 1B and 3 hereinafter). — substituent (wherein X is O, S, S(O) or S(O)) or a 0012. Therefore, in a first aspect of the present invention, heteroatom-containing-spirocyle at the 5-position of the there is provided a compound of formula (I): cyclohexane-1,3-dione, and having herbicidal properties. WO 2008/110307 A1 (Syngenta Participations AG) discloses 2-(substituted-phenyl)-5-heterocyclyl-cyclohexane-1,3-di (I) one compounds and derivatives, and their use as herbicides. WO 2010/046194A1 (Syngenta Limited) discloses 2-(sub stituted-phenyl)-cyclohexane-1,3-dione compounds and derivatives, containing a Q-CR'R' substituent at the 5-po sition of the cyclohexane-1,3-dione (wherein Q is a saturated or mono-unsaturated heterocycle), and having herbicidal properties. 0008 WO 2008/145336A1 and A8 (Syngenta Limited) disclose herbicidally active phenyl-substituted bicyclic (car bon-bridged, e.g. alkanediyl-bridged) 1..3-dione compounds, such as 3-(substituted-phenyl)-bicyclo[3.2.1]octane-2,4-di OS. US 2015/0342185 A1 Dec. 3, 2015 wherein: S(O), NH, N(C-C alkyl), N(C-C fluoroalkyl), NC X is methyl or chlorine: (O)C-Calkyl). NIC(O)C-C-fluoroalkyl or N(C- R" is methyl or chlorine; Calkoxy) moiety; R is hydrogen, methyl, ethyl, n-propyl, cyclopropyl, vinyl, 10015 C-C cycloalkyl substituted by one substituent ethynyl, fluorine, chlorine, bromine, C-Calkoxy, being C-Calkoxy (in particular C-Calkoxy) and C-C-fluoroalkoxy, C-Calkoxy-C-Calkoxy-, O optionally further substituted by one substituent being C fluoroalkoxy-C-Calkoxy-; and C-Calkyl (in particular methyl); R. R. RandR', independently of each other, are hydrogen, 0016 Cs-Cocycloalkenyl or Cs-Cocycloalkenyl substi C1-C5 alkyl (in particular C-C alkyl, e.g. C-C alkyl). tuted by one or two C-C alkyl (in particular methyl) C2-Calkenyl (in particular C-Calkenyl-CH , e.g. ethe Substituents; nyl-CH2-), C-C alkynyl (in particular C-C alkynyl 0017 C-CacycloalkylC-Calkyl- (in particular CH . C.9. ethynyl-CH ), C-C fluoroalkyl, Cs-Cocycloalkylmethyl-) or C-CacycloalkylC-Calkyl- (in C-CalkoxyC-Calkyl, C-C alkylthioC-Calkyl, particular C-Cacycloalkylmethyl-) substituted by one or two C-C alkylsulfinylC-Calkyl, C-C alkylsulfonylC ring substituents which independently are C-C alkyl or Calkyl, C-Cacycloalkyl (in particular cyclopropyl); or an C-C-fluoroalkyl; and in which one ring CH moiety of a unsubstituted 4, 5 or 6 (e.g.
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