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Pyrandione, Thiopyrandione and Cyclohexanetrione Compounds Having Herbicidal Properties

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Pyrandione, Thiopyrandione and Cyclohexanetrione Compounds Having Herbicidal Properties (19) TZZ ¥¥¥_T (11) EP 2 527 333 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.: 28.11.2012 Bulletin 2012/48 C07D 263/32 (2006.01) C07D 277/24 (2006.01) C07D 293/06 (2006.01) C07D 333/10 (2006.01) (2006.01) (2006.01) (21) Application number: 12170624.6 C07D 403/04 C07D 409/04 C07D 417/04 (2006.01) A01N 43/76 (2006.01) (2006.01) (22) Date of filing: 26.06.2008 A01N 43/78 (84) Designated Contracting States: (72) Inventors: AT BE BG CH CY CZ DE DK EE ES FI FR GB GR • Jeanmart, Stephane André Marie HR HU IE IS IT LI LT LU LV MC MT NL NO PL PT 4332 Stein (CH) RO SE SI SK TR • Mathews, Christopher John Bracknell, Berkshire RG42 6EY (GB) (30) Priority: 28.06.2007 GB 0712653 • Taylor, John Benjamin Bracknell, Berkshire RG42 6EY (GB) (62) Document number(s) of the earlier application(s) in • Smith, Stephen Christopher accordance with Art. 76 EPC: Bracknell, Berkshire RG42 6EY (GB) 08784557.4 / 2 173 727 • Phadte, Mangala 403110 Goa (IN) (71) Applicant: Syngenta Limited Guildford Remarks: Surrey GU2 7YH (GB) This application was filed on 01-06-2012 as a divisional application to the application mentioned under INID code 62. (54) Pyrandione, thiopyrandione and cyclohexanetrione compounds having herbicidal properties 5 (57) Pyrandione, thiopyrandione and cyclohexane- wherein Y is O, C=O, S(O)m or S(O)nNR ; provided that trione compounds having herbicidal properties have when Y is C=O, R3 and R4 are different from H when been found. Accordingly, the invention relates to a com- either R1 or R2 is H, and R1 and R2 are different from H pound of formula I when either R3 or R4 is H; m is 0 or 1 or 2 and n is 0 or 1; and Het is an optionally substituted monocyclic or bicyclic heteroaromatic ring (heteroaryl), as defined in the de- scription; and G is hydrogen, an alkali metal, alkaline earth metal, sul- fonium, ammonium or a latentiating group. EP 2 527 333 A1 Printed by Jouve, 75001 PARIS (FR) EP 2 527 333 A1 Description [0001] The present invention relates to novel, herbicidally active cyclic diones, and derivatives thereof, to processes for their preparation, to compositions comprising those compounds, and to their use in controlling weeds, especially in 5 crops of useful plants such as rice, corn, cereals, cotton, soya, sugarbeet, oilseed rape or canola, sugar cane, or in inhibiting plant growth. [0002] Cyclic diones having herbicidal action are described, for example, in WO 01/74770. [0003] Novel pyrandione, thiopyrandione and cyclohexanetrione compounds having herbicidal and growth-inhibiting properties have now been found. 10 [0004] The present invention accordingly relates to compounds of formula I 15 20 wherein 1 2 3 4 R ,R,R and R , independently of each other, are hydrogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxyC1-C4 alkyl, 25 C1-C4alkylthioC1-C4alkyl, C1-C4alkylsulfinykC1-C4alkyl, C1-C4alkylsulfonylC1-C4alkyl, cyclopropyl or cyclopropyl sub- stituted by C1-orC2alkyl, C1-orC2 haloalkyl or halogen; cyclobutyl or cyclobutyl substituted by C1-orC2 alkyl; oxetanyl or oxetanyl substituted by C1-orC2 alkyl; C5-C7cycloalkyl or C5-C7cycloalkyl substituted by C1-or C2alkyl or C1-or C2haloalkyl, where a methylene group of the cycloalkyl moiety is optionally replaced by an oxygen or sulfur atom or a sulfinyl or sulfonyl group; C4-C7cycloalkenyl or C4-C7cycloalkenyl substituted by C1-orC2alkyl or C1-orC2haloalkyl, 30 where a methylene group of the cycloalkenyl moiety is optionally replaced by an oxygen or sulfur atom or a sulfinyl or sulfonyl group; cyclopropylC1-C5alkyl or cyclopropylC1-C5alkyl substituted by C1-orC2alkyl, C1-orC2haloalkyl or hal- ogen; cyclobutylC1-C5alkyl or cyclobutylC1-C5alkyl substituted by C1-C2 alkyl; oxetanylC1-C5alkyl or oxetanylC1-C5alkyl substituted by C1-orC2alkyl; C5-C7cycloalkylC1-C5alkyl or C5-C7cycloalkylC1-C5alkyl substituted by C1-orC2alkyl or C1-orC2haloalkyl, where a methylene group of the cycloalkyl moiety is optionally replaced by an oxygen or sulfur atom 35 or a sulfinyl or sulfonyl group; C4-C7cycloalkenylC1-C5alkyl or C4-C7cycloalkenylC1-C5alkyl which is substituted by C1- or C2alkyl or C1-orC2haloalkyl, where a methylene group of the cycloalkenyl moiety is optionally replaced by an oxygen or sulfur atom or a sulfinyl or sulfonyl group; phenyl or phenyl substituted by C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl, halogen, nitro, cyano, C1-C4 alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl or C1-C4alkylcarbonyl; benzyl or benzyl substituted by C1-C4alkyl, C1-C4 alkoxy, C1-C4haloalkyl, halogen, nitro, cyano, C1-C4 alkylthio, C1-C4alkylsulfinyl, 40 C1-C4alkylsulfonyl or C1-C4alkylcarbonyl; or heteroaryl or heteroaryl substituted by C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl, halogen, nitro, cyano, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl or C1-C4alkylcarbonyl; or R1 and R2,orR3 and R4, are joined to form a 3-7 membered saturated ring in which a methylene group is optionally replaced by an oxygen or sulfur atom, and which may be optionally substituted by C1-orC2-alkyl, halogen or C1-C2 alkoxy, or a 5-7 membered unsaturated ring in which a methylene group is optionally replaced by an oxygen or sulfur 45 atom, and which may be optionally substituted by C1- or C2-alkyl, halogen or C1-C2 alkoxy; or R1 and R3 are joined to form a 5-7 membered saturated or unsaturated ring or a 5-7 membered saturated or unsaturated ring optionally substituted by C1- or C2alkyl, C1- or C2alkoxy, hydroxy or halogen; and 5 3 4 1 Y is O, C=O, S(O)m or S(O)nNR ; provided that when Y is C=O, R and R are different from hydrogen when either R or R2 is hydrogen, and R1 and R2 are different from hydrogen when either R3 or R4 is hydrogen; m is 0 or 1 or 2 and n is 0 or 1; 50 5 R is hydrogen, C1-C6alkyl, C3-C6cycloalkyl, C1-C6alkoxycarbonyl, tri(C1-C6alkyl)silyl-ethyloxycarbonyl, C1-C6haloalkoxycarbonyl, cyano, C1-C6haloalkyl, C1-C6hydroxyalkyl, C2-C6alkenyl, C2-C6alkynyl, C2-C6haloalkenyl, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C6cycloalkylcarbonyl, phenylcarbonyl or phenylcarbonyl substituted by R6; benzylcarbonyl or benzylcarbonyl substituted by R6; pyridylcarbonyl or pyridylcarbonyl substituted by R6; phenox- ycarbonyl or phenoxycarbonyl substituted by R6; benzyloxycarbonyl or benzyloxycarbonyl substituted by R6; 55 6 R is C1-C6haloalkyl, C1-C6alkoxycarbonyl, nitro, cyano, formyl, carboxyl or halogen; Het is a group of the formula R1 to R12 2 EP 2 527 333 A1 5 10 15 20 25 30 wherein A designates the point of attachment to the ketoenol moiety, and W1 is N or CR10; W2 and W3 are independently of each other N or CR8; 35 W4 is N or CR11; with the proviso that at least one of W1, W2, W3 or W4 is N; X is O, S, Se, or NR13; Z is N or CR14; 7 R is halogen, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C1-C4 40 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, nitro or cyano; 8 R is hydrogen, halogen, cyano, nitro, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 alkoxy, C2-C4 alkenyloxy, C1-C4 alkylthio, C1-C4 alkylsulphinyl, C1-C4 alkylsulphonyl, C1-C4 alkoxy C1-C4 alkyl, poly C1-C4 alkoxyC1-C4 alkyl, C1-C4 alkylthio C1-C4 alkyl, each of which is unsubstituted or substituted by halogen, or C3-C8cycloalkyl, thienyl, furyl, pyrrolyl, isoxazolyl, oxazolyl, isothiazolyl, thiazolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, oxadiazolyl, thia- 45 diazolyl, pyridazinyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl or quinoxalinyl, or an N-oxide or a salt thereof, each of these substituents being unsubstituted or substituted by halogen, C1-C4 alkyl, haloC1-C4 alkyl, C1-C4 alkoxy, C2-C4 alkenyloxy, C1-C4 alkylthio, C1-C4 alkylsulphinyl, C1-C4 alkyl-sulphonyl, haloC1-C4 alkyl, haloC1-C4 alkoxy, cyano or nitro; 9 R is hydrogen, C1-C4 alkyl, C2-C3alkenyl, C2-C3alkynyl, C1-C4 haloalkyl or C2-C3 haloalkenyl; R10 is hydrogen, methyl, halomethyl or halogen; 50 11 R is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl or cyano; 12 R is hydrogen, methyl, ethyl, halomethyl, haloethyl, aryl, aryl substituted by C1-C2-alkyl, C1-C2-alkoxy, C1-C2 haloalkyl, C1-C2 haloalkoxy, cyano or nitro, heteroaryl or heteroaryl substituted by C1-C2-alkyl, C1-C2-alkoxy, C1-C2 haloalkyl, C1-C2 haloalkoxy, cyano or nitro; 55 R13 is hydrogen, methyl or halomethyl; and R14 is hydrogen, methyl, ethyl, halomethyl, haloethyl, halogen, cyano or nitro; and wherein: G is hydrogen, an alkali metal, alkaline earth metal, sulfonium, ammonium or a latentiating group. 3 EP 2 527 333 A1 [0005] In the substituent definitions of the compounds of the formula I, the alkyl substituents and alkyl moieties of alkoxy, alkylamino etc. having 1 to 6 carbon atoms are preferably methyl, ethyl, propyl, butyl, pentyl and hexyl, in the form of their straight and branched isomers. The alkenyl and alkynyl radicals having 2 to 6 carbon atoms as well as up to 10 carbon atoms can be straight or branched and can contain more than 1 double or triple bond. Examples are vinyl, 5 allyl, propargyl, butenyl, butynyl, pentenyl and pentynyl. Suitable cycloalkyl groups contain 3 to 7 carbon atoms and are for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. Cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl are preferred. Heterocycles, as a rule, correspond to the carbocycles or cycloalkyl radicals mentioned above with the exception that one or two methylene groups are replaced by an oxygen, sulphur or nitrogen atom, which can be substituted further.
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