GB2511386A - Herbicidal compositions - Google Patents

Abstract

The present invention provides a herbicidal composition comprising: (a) a compound of formula (I) or an agriculturally acceptable salt thereof: wherein the substituents are as defined herein; and (b) an ALS (acetolactate synthase) inhibitor herbicide suitable for use on rice, wherein the rice-suitable ALS inhibitor herbicide is bensulfuron-methyl, pyrazosulfuron-ethyl, azimsulfuron, flucetosulfuron, orthosulfamuron, prosulfuron, triasulfuron, trifloxysulfuron, bispyribac, pyriminobac-methyl, pyribenzoxim, and/or penoxsulam, or an agriculturally acceptable salt of any of these; and wherein the weight ratio of the compound of formula (I) or the salt thereof, (calculated as the free compound), to the rice-suitable ALS inhibitor herbicide, (calculated as the free compound), is as defined herein. Also claimed is a composition comprising (a) and (b) and a safener. The invention also relates to a method of controlling grassy weeds (e.g. Brachiaria, Echinochloa, and/or Leptochloa) in crops of useful plants (e.g. rice), which comprises applying the composition to the grassy weeds or to the locus (particularly to the flooded locus, e.g. floodwaters) thereof.

Description

Intellectual Property Office Application No. GB1321409.3 RTM Date:26 June 20t4 The following terms are registered trade marks and should be read as such wherever they occur in this document: Emulsogen N an s a Solvesso Permit Sirius Intellectual Property Office is an operating name of the Patent Office www.ipo.govuk Herbicidal compositions The present invention relates to a herbicidal composition, for example suitable for controlling weeds (e.g. grassy weeds) in crops of useful plants, especially in crops of rice; which composition comprises (a) a herbicidally active pyrandione [preferably a biphenyl pyrandione; more preferably a 4- (substituted biphenyl-3-yl)-2H-pyran-3,5(4H,6H)-dione, even more preferably a 4-(substituted biphenyl-3-y-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione, for example a 4-(4-ethyl or 4- cyclopropyl, 2-chloro-or 2-fluoro-, 4'-chloro-biphenyl-3-yl)-2,2,6,6-tetramethyl-2H-pyran- 3,5(4H,6H)-dione]; or an enol ketone tautomer thereof; or a derivative (preferably an ester or carbonate derivative, such as a methyl ester or methyl carbonate derivative) of a biphenyl pyrandione (preferably as defined herein), for example a methyl carbonate derivative of 4-(4-ethyl-2',4'-dichloro-biphenyl-3-y-2,2,6,6-tetramethyl-2/-1-pyran-3,5 (4H,6/--dione; and (b) a selected acetolactate synthase (ALS) inhibitor herbicide suitable for use on rice.

The present invention also relates to a method of controlling weeds in crops of rice comprising applying the herbicidal composition.

WO 2008/071405 Al (Syngenta Participations AG and Syngenta Limited) discloses pyrandione, thiopyrandione and cyclohexanedione compounds, and enol ketone tautomer derivatives thereof, suitable for use as herbicides. wa 2008/071405 Al also discloses mixtures of these pyrandione, thiopyrandione or cyclohexanedione compounds with any of a large number of herbicidal mixture partners. Three of the many specific pyrandione herbicidal compounds disclosed in WO 2008/071405 Al are compound A-45 (on PCT page 93), compound A-66 (on PCI page 95), and compound D-26 (on PCT page 231) whose structures are as follows: 4'"J%.1%% 1Ii compound NumberA-45 compound NumberA-66 Compound Number D-26 from WO 20081071405 Al from WO 2008/071405 Al from wa 2008/071405 Al Wa 201 0/136431 A9 (Syngenta Limited) discloses a genus of spirocyclic epoxy ketones, and their use as intermediates in the preparation of herbicidally active substituted 4-phenyl-3,5-pyrandiones, 4-phenyl-3,5-thiopyrandiones and 6-phenylcyclohexane-l,3,5-triones including those disclosed in WO 2008/071405 Al. Three of the several specific pyrandione compounds disclosed in WO 2010/136431 A9 are Example P8 (POT pages 31-32 and 35- 36), Example P9 (POT pages 36-37 and 40-41), and Example PlO (POT pages 41 and 44- 45), whose structures are shown below: Example P8 from Example P9 from Example PlO from Wa 2010/136431 A9 WO 2010/136431 A9 Wa 2010/136431 A9 WO 2011/073615A2 (Syngenta Limited) discloses herbicidal compositions comprising (a) a genus of inter a/ia 4-(4-(R1-substituent)-biphenyl-3-yl)-2,2,6,6-tetraalkyl-2H-pyran- 3,5(4H,6/-O-dione or derivative compounds in which the R1-substituent is methyl, ethyl, n-propyl, halogen, difluoromethoxy, trifluoromethoxy ortrifluoromethyl, in particular one of the three pyrandione compounds A-4, A-7 and A-9 shown below; and (b) a co-herbicide selected from the group consisting of fenoxasulfone, ipfencarbazone, propyrisulfuron, and N-[2-[(4,6- dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1, 1 -difluoro-N-methylmethanesulfonamide; and the use of these herbicidal compositions on inter a/ia rice crops and/or to control Echinochloa and/or Leptochloa weeds: I jfJ%11% I compound A-4 from compound A-7 from Compound A-9 from wa 2011/073615A2 W02011/073615A2 WO 2011/073615 A2 WO 2011/073616 A2 (Syngenta Limited) discloses herbicidal compositions comprising (a) a genus of 4-(4-cyclopropyl-biphenyl-3-yl)-2,2,6,6-tetraalkyl-2H-pyran-3,5(4H,6H) -dione or derivative compounds, in particular one of the two pyrandione compounds A-12 and A-13 shown below; and (b) a co-herbicide selected from the group consisting of fenoxasulfone, ipfencarbazone, propyrisulfuron, and N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1, 1 -difluoro-N-methylmethanesulfonamide; and the use of these compositions inter a/ia on rice crops to control weeds; and also discloses inter a/ia the use of compound A- 13 to control weeds (e.g. Echinochloa and/or Leptochloa weeds) in crops of rice: _Li5L, compound A-12 from compound A-13 from Without being bound by theory, and without being able to confirm this by experiment, the five specific biphenyl pyrandione compounds illustrated above, which were specifically disclosed in one or more ofWO 2008/071405 Al, WO 2010/136431 A9, WO 2011/073615 A2 and WO 2011/073616 A2, are thought to exhibit herbicidal activity against grassy monocotyledonous weeds by virtue of being able to inhibit aceM-CoA carboxyase (ACCase) within the target weeds, which is likely to lead to the inhibition of lipid synthesis within the target weeds.

It is desirable to discover new mixtures of certain pyrandione compounds or enol-ketone-tautomer-derivative compounds disclosed in WO 2008/071405 Al and/or WO 2010/136431 A9 and/or WO 2011/073615 A2 and/or WO 2011/073616 A2 with other co-herbicides, especially: i) a mixture suitable for use in crops of rice, for example either transplanted flooded rice (e.g. using post-emergent application to the flood-waters) or direct-seeded rice (e.g. using post-emergent foliar and/or spray application), preferably having low or relatively low levels of phytotoxicity on the rice crops; and/or ii) mixtures suitable to control certain grassy monocotyledonous weeds such as Echinochloa, Brachiaria and/or Leptochloa, which are often found in rice crops, while also having activity against certain sedges and/or certain broadleaf and/or dicotyledonous weeds which can be found in rice crops.

Surprisingly, in field trials (Biological Example 3 hereinafter), a mixture of one such pyrandione,,Compound no. 1' (as defined hereinafter) using an EC 050 formulation thereof, tank-mixed with either (i) the sulfonyl urea rice herbicide pyrazosulfuron-ethyl or (ii) the sulfonyl urea rice herbicide bensulfuron-methyl, and then applied generally post-emergence to the floodwaters of transplanted rice, showed the unexpected benefit of improved rice crop tolerance (decreased phytotoxicity on rice), compared to the application of the Compound no. 1 alone.

Also, in Biological Example 4 hereinafter, studying e.g. Compound no. 1 (within the compound of formula (I) or (IA)) + Safener no. 1 + 21 g ai/ha pyrazosulfuron-ethyl in transplanted rice, rice crop tolerance was variable depending mainly on the location and soil types. In sandy clay loam the level of (maximum) damage to rice was higher reaching 23% at 120 g ai/ha of Compound no. 1. However the three way mixture Compound no. 1 + Safener no. 1 + pyrazosulfuron-ethyl gave a noticeable improvement of the margin of rice selectivity by delivering a good level of Echinochloa control already at the rate of 60 g ai/ha Compound no. 1 +30 g ai/ha Safener no. 1 + 21 g ai/ha pyrazosulfuron-ethyl (ai = active ingredient). A close look at all the field results showed that there was a clear pattern between the crop tolerance and the soil type, where the higher the soil sand content was, the higher the risk of crop injury. Whilst Compound no. 1 applied alone (solo) at 60 and 90 g ai/ha was injurious on rice up to 28% (maximum rice phytotoxicity) in soils with more than 60% of sand, the three way mixture of Compound no. 1 + Safener no. 1 + pyrazosulfuron-ethyl gave no more than 18% of (maximum) rice phytotoxicity in the same extreme soil conditions, demonstrating a clear safening effect, which is believed to be (surprisingly) at least partly caused by the presence of pyrazosulfuron-ethyl.

In Biological Example 5 hereinafter, laboratory (hydroponics) studies on root uptake shed some light on the possible mechanism associated with the unexpected safening effect of three way mixture Compound no. 1 + Safener no. 1 + pyrazosulfuron-ethyl seen in Biological Example 4. Mixing Compound no. 1 with pyrazosulfuron-ethyl resulted in a surprising reduction of up to five-fold of the root uptake into rice. Thus, a great and unexpected reduction of root uptake in rice by pyrazosulfuron-ethyl could explain the safening effects (i.e. reduced rice phytotoxicity) shown in the field (see Biological Example 4 and also Biological Example 3) with the three way mixture of Compound no. 1 + Safener no. 1 + pyrazosulfuron-ethyl.

A first aspect of the present invention provides a herbicidal composition comprising: (a) a compound of formula (I) or an agriculturally acceptable salt thereof: R R (I), wherein: R1 is methyl, ethyl, n-propyl, cyclopropyl, fluorine, chlorine, bromine, difluoromethoxy or trifluoromethoxy; R2 is phenyl or phenyl substituted by 1, 2 or 3 (e.g. 1 or 2) substituents independently being halogen, C1C2 alkyl, C1C2 fluoroalkyl, 01-C2 alkoxy, C1-C2 fluoroalkoxy or cyano; and either R4, R5, R6 and R7, independently of each other, are hydrogen, 01-03 alkyl, n-butyl or C1-C2alkoxyC1-C2alkyl; or R4 and R7 together are methanediyl, ethane-1,2-diyl or propane-i,3-diyl each of which is optionally substituted by one or two methyl substituents, or R4 and R7 together are ethene- 1,2-diyl optionally substituted by one or two methyl substituents; and R5 and R6, independently of each other, are hydrogen, ClC3 alkyl, n-butyl or 01-C2alkyoxyC1-C2alkyl; and G is hydrogen, an alkali metal, alkaline earth metal, sulfonium, or ammonium, orG is -C(o)-R2 or wherein R is H, C1-C18alkyl, C2-C18alkenyl, C2-C13alkynyl, C1-C10fluoroalkyl, C2 C5fluoroalkenyl, 03-C3cycloalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C1-C10aminoalkyl, C- C5alkylaminoC1-C5alkyl, CrCadialkylaminoCi-Csalkyl, C3-C7cycloalkylC1-C5alkyl, C- C5alkoxyC1-C5alkyl, (C2-C4alkenyl-methoxy)C1-C5alkyl, (02-C4alkynyl-methoxy)C1-C5alkyl, C-C5alkylthioC1-C5alkyl, C1-C5alkylsulfinylc1-C5alkyl, C1-C5alkylsulfonylC1-C5alkyl, C2 C8alkylideneaminoxyC1-C5alkyl, C1-C5alkylcarbonylC1-C5alkyl, C1-C5alkoxycarbonylC1-C5alkyl, aminocarbonylC1-C5alkyl, C1-C5alkylaminocarbonylC1-C5alkyl, C2 C3dialkylaminocarbonylC1-C5alkyl, 01-C5alkylcarbonylaminoC1-C5alkyl, N-C1-C5alkylcarbonyl-N-C1-C5alkylaminoC1-C5alkyl, 03-C5trialkylsilylc1-C5alkyl, phenylC1-C5alkyl (wherein the phenyl is optionally substituted by 1,2 or3 (e.g. 1)substituents independently being C-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, fluorine, chlorine, bromine, cyano, or nitro), heteroarylC1-C5alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 (e.g. 1) substituents independently being C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, fluorine, chlorine, bromine, cyano, or nitro); phenyl or phenyl substituted by 1, 2 or 3 (e.g. 1) substituents independently being C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C-C3fluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro; or heteroaryl or heteroaryl substituted by 1,2 cr3 (e.g. 1) substituents independently being C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, fluoline, chlorine, bromine, cyano or nitro; and RL is C1-C18alkyl, C2-C17alkenyl-CH2-, C2-C16alkenyl-CHMe-, C2-C15alkenyl-CMe2-, C2- C17alkynyl-CH2-, CrCi6alkynyl-CHMe-, CrCisalkynyl-CMe2-, C2-C10fluoroalkyl, 02- C4fluoroalkenyl-CH2-, C2-C3fluoroalkenyl-CHMe-, C2fluoroalkenyl-CMe2-, C3-C8cycloalkyl, C1- C10cyanoalkyl, C1-C10nitroalkyl, C2-C10aminoalkyl, C1-C5alkylaminoC1-C5alkyl, C2- C6dialkylaminoC1-C5alkyl, C3-C7cycloalkylC1-C5alkyl, C1-C5alkoxyC1-C5alkyl, (C2-C4alkenyl- methoxy)C1-C5alkyl, (CC4alkynyl-methoxy)C1-C5alkyl, C1-C5alkylthioC1-C5alkyl, C1- C5alkylsulfinylC1-C5alkyl, C1-C5alkylsulfonylC1-C5alkyl, C2-C8alkylideneaminoxyC1-C5alkyl, C- C5alkylcarbonylo1-C5alkyl, C1-C5alkoxycarbonylC1-C5alkyl, aminocarbonylC1-C5alkyl, Ci- C5alkylaminocarbonylC1-C5alkyl, C2-C8dialkylaminocarbonylC1-C5alkyl, C- C5alkylcarbonylaminoC1-C5alkyl, N-C1-C5alkylcarbonyl-N-C1-C5alkylaminoC1-C5alkyl, C3-C6trialkylsilylC1-C5alkyl, phenylC1-C5alkyl (wherein the phenyl is optionally substituted by 1,2 or 3 (e.g. 1) substituents independently being C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, fluorine, chlorine, bromine, cyano, or nitro), heteroarylC1-C5alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or3 (e.g. 1) substituents independently being C-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, fluorine, chlorine, bromine, cyano, ornitro); phenylorphenylsubstituted by 1,2 or3(e.g. 1) substituents independently being C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro; or heteroaryl or heteroaryl substituted by 1, 2 or 3 (e.g. 1) substituents independently being C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro; and (b) an ALS (acetolactate synthase) inhibitor herbicide suitable for use on rice; wherein the rice-suitable ALS inhibitor herbicide is bensulfuron-methyl, pyrazosulfuron-ethyl, azimsulfuron, flucetosulfuron, orthosulfamuron, prosulfuron, triasulfuron, trifloxysulfuron, bispyribac, pyriminobac-methyl, pyribenzoxim, and/or penoxsulam, or an agriculturally acceptable salt of any of these; and wherein the weight ratio of the compound of formula (I) or the salt thereof, calculated as the free compound, to the rice-suitable ALS inhibitor herbicide, calculated as the free compound, is as follows: if bensulfuron-methyl or a salt thereof is present, then the weight ratio of the compound of formula (I) to bensulfuron-methyl is from 180:20 to 10:120, or from 150:20 to 10:120; if pyrazosulfuron-ethyl or a salt thereof is present, then the weight ratio of the compound of formula (I) to pyrazosulfuron-ethyl is from 180:7 to 10:60, or from 150:7 to 10:60; if azimsulfuron or a salt thereof is present, then the weight ratio of the compound of formula (I) to azimsulfuron is from 180:7 to 10:50, or from 150:7 to 10:50; if flucetosulfuron or a salt thereof is present, then the weight ratio of the compound of formula (I) to flucetosulfuron is from 180:7 to 10:60, or from 150:7 to 10:60; if orthosulfamuron or a salt thereof is present, then the weight ratio of the compound of formula (l)to orthosulfamuron is from 180:15 to 10:150, or from 150:15 to 10:150; if prosulfuron or a salt thereof is present, then the weight ratio of the compound of formula (I) toprosulfuron isfrom 180:4to 10:60, orfrom 150:4to 10:60; if triasulfuron or a salt thereof is present, then the weight ratio of the compound of formula (I) totriasulfuron is from 180:1.5 to 10:20, or from 150:1.5 to 10:20; if trifloxysulfuron or a salt thereof is present, then the weight ratio of the compound of formula (I) to trifloxysulfuron is from 180:1.5 to 10:100, or from 150:1.5 to 10:100; if bispyribac or a salt thereof is present, then the weight ratio of the compound of formula (I) tobispyribacisfrom 180:lOto 10:70, orfrom 150:lOto 10:70; if pyriminobac-methyl or a salt thereof is present, then the weight ratio of the compound of formula (I) to pyriminobac-methyl is from 180:12 to 10:175, orfrom 150:12 to 10:175; if pyribenzoxim or a salt thereof is present, then the weight ratio of the compound of formula (I) to pyribenzoxim is from 180:10 to 10:70, or from 150:10 to 10:70; and if penoxsulam or a salt thereof is present, then the weight ratio of the compound of formula (I) to penoxsulam is from 180:2 to 10:60, or from 150:2 to 10:60.

Particularly preferably, the compound of formula (I) or the agriculturally acceptable salt thereof is a compound of formula (IA) or a compound of formula (IB) or an agriculturally acceptable salt of either of these: (IA) (IB), wherein, in formula (IA), R1 is ethyl or cyclopropyl, and R2A is hydrogen, chlorine or fluorine.

Most preferably, in all aspects or embodiments of the invention, in formula (IA), RM is chlorine or fluorine.

The invention, in a second aspect, also relates to a method of controlling weeds, especially monocotyledorious weeds (in particular grassy weeds in particular Brachiaria, Echinochloa, and/or Leptochloa), in crops of useful plants, which comprises applying the herbicidal composition to the weeds, e.g. monocotyledonous e.g. grassy monocotyledonous weeds, or to the locus thereof.

A second aspect of the present invention also relates to a method of controlling weeds in crops of useful plants, which comprises applying a herbicidal composition as defined in the first aspect of the invention to the weeds and/or useful plants (preferably flooded weeds and/or flooded useful plants) and/or to the locus (preferably to the flooded locus) thereof.

(More preferably, the method comprises applying the herbicidal composition to the flood-waters at the flooded locus of the flooded weeds and/or flooded useful plants).

In the present invention, and throughout this specification, "calculated as the free compound" or "measured as the free compound" means that the weight of the stated compound is calculated (or measured) (a) by including the weight of the stated compound and (b) by excluding the weight of any salt counter-ions which may or may not be present or associated with the stated compound. For example, when the the rice-suitable ALS inhibitor herbicide is bispyribac-sodium, which is the sodium salt of bispyribac, then the weight of the bispyribac (the free compound) is included and the weight of the sodium ions (counter-ions) is excluded, when calculating the weight of the free compound.

Typically, the herbicidal composition comprises: (a) a herbicidally effective amount of the compound of formula (I) or the agriculturally acceptable salt thereof, and (b) a herbicidally effective amount of the rice-suitable ALS inhibitor herbicide.

The preferred, suitable, particular, optional and/or other features of the compound of formula (I), in particular the preferred, suitable, particular, optional and/or other values of the substituents G, R1, R2, R3, R4, R5, R6, and/or R7 in the compound of formula (I), are set out below (and/or generally herein). These features can be either taken alone or taken together, in any combination(s) thereof, with one or more of any other preferred, suitable, particular, optional and/or other features of any of the present inventions as follows: (i) features of the compound of formula (I), and/or (ii) features of the rice-suitable ALS inhibitor herbicide, and/or (iü) features of the weight ratio(s) of the compound of formula (I) to the rice-suitable ALS inhibitor herbicide in the herbicidal composition, and/or (iv) features of any of the uses or formulations of the herbicidal composition (e.g. crops, weeds, application methods, application rates and/or composition/formulation ingredients).

Preferably, in all aspects or embodiments of the invention, in the compound of formula (I), R1 is methyl, ethyl, n-propyl, cyclopropyl, chlorine, bromine, difluoromethoxy ortrifluoromethoxy.

More preferably, R1 is methyl, ethyl, cyclopropyl, chlorine, difluoromethoxy or trifluoromethoxy. Most preferably, R1 is ethyl or cyclopropyl.

Preferably, in all aspects or embodiments of the invention, in the compound of formula (I), 2 is phenyl substituted by 1,2 or3 (e.g. 1 or2)substituents independently being halogen (in particular fluorine, chlorine or bromine, preferably fluorine or chlorine), C1C2 alkyl (in particular methyl), 01-02 fluoroalkyl (in particular C fluoroalkyl, such as CF3 or CHF2), C1-C2 alkoxy (in particular methoxy), 01-02 fluoroalkoxy (in particular C fluoroalkoxy, such as 0F30 orCHF2O), orcyano. More preferably, R2 is phenyl substituted by 1,2 or3(e.g. 1 or2) substituents independently being halogen (in particular fluorine, chlorine or bromine, preferably fluorine or chlorine), 01-02 alkyl (in particular methyl), 01-02 fluoroalkyl (in particular C fluoroalkyl, such as CF3 or CHF2), 01-02 alkoxy (in particular methoxy), 01-02 fluoroalkoxy (in particular C fluoroalkoxy, such as 0F30 or CHF2O), or cyano, wherein the 4-position of the phenyl is substituted (preferably the 4-position of the phenyl is substituted by a halogen, more preferably by chlorine or fluorine). Even more preferably, R2 is phenyl substituted at the 4-position by chlorine or fluorine (or more preferably by chlorine), and optionally further substituted by 1 or 2 (e.g. 1) further substituents independently being fluorine, chlorine, methyl, C fluoroalkyl (in particular CF3 or OH F2), methoxy, C fluoroalkoxy (in particular CF3O or CHF2O), or cyano; or R2 is 4-bromophenyl, 4-iodophenyl or 4-trifluoromethoxyphenyl.

Still more preferably, in the compound of formula (I), R2 is 4-chlorophenyl, 4-bromophenyl, 4-iodophenyl, 4-trifluoromethoxyphenyl, 2,4-dichlorophenyl, 4-chloro-2-fluorophenyl, 4-chloro-2-methylphenyl, 4-chloro-2-difluoromethylphenyl, 4-chloro-2-methoxyphenyl, 4-chloro-2-cyanophenyl, 3,4-dichlorophenyl, 4-chloro-3-trifluoromethylphenyl, 4-chloro-3-methoxyphenyl, 4-chloro-3-trifluoromethoxyphenyl, 4-chloro-3-cyanophenyl, 2,4,5-trichlorophenyl, 4-chloro-2-fluoro-3-trifluoromethylphenyl, 3,4-dichloro-2-fluorophenyl, 2,4-dichloro-3-fluorophenyl, 2,4-dichloro-5-fluorophenyl, 4-chloro-2,6-difluorophenyl, 4-chloro-2,5-difluorophenyl, or 2,4,5-trifluorophenyl.

Yet more preferably, R2 is 4-chlorophenyl, 2,4-dichlorophenyl, 4-chloro-2-fluorophenyl, 4-chloro-2-methylphenyl, 4-chloro-2-difluoromethylphenyl, 4-chloro-2-methoxyphenyl, 4-chloro-2-cyanophenyl, 3,4-dichlorophenyl, 4-chloro-3-methoxyphenyl, -ii- 4-chloro-3-cyanophenyl, 4-chloro-2-fluoro-3-trifluoromethylphenyl, or 4-chloro-2,6-difluorophenyl.

Most preferably, R2 is 4-chlorophenyl, 2,4-dichlorophenyl, 4-chloro-2-fluorophenyl, 4-chloro-2-methylphenyl, 4-chloro-2-methoxyphenyl, 4-chloro-3-methoxyphenyl, 4-chloro-3-cyanophenyl, or 4-chloro-2,6-difluorophenyl.

Preferably, in all aspects or embodiments of the invention, in the compound of formula (I), either R4, R5, R6 and R7, independently of each other, are hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, or methoxyethyl (in which case, preferably at least one (more preferably 2, 3 or 4) of R4, R5, R6 and R7 is or are not hydrogen); or R4 and R7 together are ethane-1,2-diyl or propane-i,3-diyl each of which is optionally substituted by one or two methyl substituents; and R5 and R°, independently of each other, are hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, or methoxyethyl.

More preferably, either R4, R5, R6 and R7, independently of each other, are hydrogen, methyl, ethyl or methoxymethyl (in which case, preferably at least one (more preferably 2, 3 or 4) of R4, R5, R6 and R7 is or are not hydrogen); or R4 and R7 together are unsubstituted ethane-1,2-diyl; and R5 and R6, independently of each other, are hydrogen, methyl, ethyl or methoxymethyl.

Even more preferably, R4, R5, R6 and R7, independently of each other, are hydrogen, methyl, ethyl or methoxymethyl; provided that at least one (more preferably 2, 3 or 4) of R4, R5, S6 and 7 is or are not hydrogen.

Yet more preferably, and 6, independently of each other, are hydrogen or methyl; and 4 and 7, independently of each other, are hydrogen, methyl, ethyl or methoxymethyl; provided that at least one (more preferably 2, 3 or 4) of 4, 5, 6 and 7 is or are not hydrogen.

Most preferably, 4, 5 and 6 are methyl, and 7 is hydrogen, methyl, ethyl or methoxymethyl; or 5 and 6 are methyl, and 4 and 7 are ethyl; or 4 and 5 are methyl, and 6 and 7 are hydrogen; -12-or R4 and R5 are hydrogen, and R6 and R7 are methyl.

Preferably, in all aspects or embodiments of the invention, in the compound of formula (I), R is C1-C10alkyl (preferably C1-C5alkyl or C1-C4alkyl), C2-C5alkenyl, C2-C6alkynyl, 03-C6cycloalkyl, C3-C6cycloalkyl-methyl-, or C1-C2alkoxyC1-C2alkyl. More preferably, Ra is C1-C4alkyl (in particular methyl, ethyl, isopropyl ort-butyl), allyl (CH2=CH-CH2-), propargyl (HC5C-CH), methoxymethyl or 2-methoxyethyl. Most preferably, R is C1-C4alkyl, in particular methyl, ethyl, isopropyl or t-butyl.

Preferably, in all aspects or embodiments of the invention, in the compound of formula (I), Rb is C1-C10alkyl (preferably C1-C5alkyl or C1-C4alkyl), C2-Csalkenyl-CHr, 02-C4alkenyl-CHMe-, C2-C3alkenyl-CMe, C2-C5alkynyl-CH, C2-C4alkynyl-CHMe-, CC3alkynyl-CMe, C3-C5cycloalkyl, C3-C6cycloalkyl-methyl-, or 2-(01-C2alkoxy)ethyl. More preferably, Rb is C1-C4alkyl (such as methyl, ethyl, isopropyl or t-butyl), allyl (CH2=CH-CH2-), propargyl (HCEC-CH2-), or 2-methoxyethyl; in particular C1-C4alkyl (such as methyl, ethyl, isopropyl or t-butyl). Most preferably, Rb is methyl or ethyl.

Preferably, in all aspects or embodiments of the invention, in the compound of formula (I), G is hydrogen, C(O)Ra or C(O)ORb.

Wien G is -C(O)-R3 or C(O)ORb, then in general G is a latentiating group. These latentiating groups G are selected to allow their removal by one or a combination of biochemical (e.g. enzymatic), chemical (e.g. hydrolytic or photolytic) or physical processes to afford compounds of formula (I) wherein G is H during or following application to the treated area or to the plants. Examples of these processes by which the G latentiating group may be removed include enzymatic cleavage, chemical hydrolysis and/or photolysis. Compounds bearing such latentiating groups G may in some cases exhibit certain slightly altered properties compared to the corresponding G = H compound, for example somewhat altered (e.g. somewhat improved) penetration of the cuticula of (e.g. some of) the plants to which the compound is applied.

Preferably, in the compound of formula (I), G is hydrogen, C(O)Ra or C(O)ORb, wherein Ra is C1-C10alkyl (preferably C1-C5alkyl or C1-C4alkyl), C2-C5alkenyl, C2-C5alkynyl, C-C6cycloalkyl, C3-C6cycloalkyl-methyl-, or C1-C2alkoxyC1-C2alkyl; and Rb is C1-C10alkyl (preferably C1-C6alkyl or C1-C4alkyl), C2-C5alkenyl-CH2-, C2 C4alkenyl-CHMe-, C2-C3alkenyl-CMe2-, CC5alkynyl-CH, C2-C4alkynyl-CHMe-, C2 C3alkynyl-CMe2-, C3-C3cycloalkyl, C3-C6cycloalkyl-methyl-, or 2-(C1-C2alkoxy)ethyl.

Even more preferably, G is hydrogen, -C(O)-01-C4alkyl or -C(O)-O-C1-C4alkyl. Most preferably, G can be hydrogen, -C(O)-C1-C2alkyl or -C(O)-O-C1-C2alkyl. For example, G can in particular be hydrogen.

Particularly preferably, in all aspects or embodiments of the invention, in the compound of formula (Q: R1 is methyl, ethyl, cyclopropyl, chlorine, difluoromethoxy or trifluoromethoxy (or, most preferably, R1 is ethyl or cyclopropyl); and R2 is 4-chlorophenyl, 2,4-dichlorophenyl, 4-chloro-2-fluorophenyl, 4-chloro-2-methylphenyl, 4-chloro-2-difluoromethylphenyl, 4-chloro-2-methoxyphenyl, 4-chloro-2-cyanophenyl, 3,4-dichlorophenyl, 4-chloro-3-methoxyphenyl, 4-chloro-3-cyanophenyl, 4-chloro-2-fluoro-3-trifluoromethylphenyl, or 4-chloro-2,6-difluorophenyl (or, most preferably, R2 is 4-chlorophenyl, 2,4-dichlorophenyl, 4-chloro-2-fluorophenyl, 4-chloro-2-methylphenyl, 4-chloro-2-methoxyphenyl, 4-chloro-3-methoxyphenyl, 4-chloro-3-cyanophenyl, or 4-chloro- 2,6-difluorophenyl); and R5 and R6, independently of each other, are hydrogen or methyl; and R4 and R7, independently of each other, are hydrogen, methyl, ethyl or methoxymethyl; provided that at least one (more preferably 2, 3 or 4) of R4, R5, R8 and R7 is or are not hydrogen; (or, most preferably: R4, R5 and R6 are methyl, and R7 is hydrogen, methyl, ethyl or methoxymethyl; or R5 and R6 are methyl, and R4 and R7 are ethyl; or R4 and R5 are methyl, and R6 and R7 are hydrogen; or R4 and R5 are hydrogen, and R6 and R7 are methyl); and G is hydrogen, -C(O)-C1-C4alkyl or -C(O)-O-C1-C4alkyl (or, most preferably, 0 is hydrogen, -C(O)-C1-C2alkyl or -C(O)-O-C1-C2alkyl; for example, 0 can in particular be hydrogen).

Preferably, in all aspects of the invention, the compound of formula (I) or the agriculturally acceptable salt thereof comprises (preferably is): -14-one of the following compounds: A-4, D-7, D-8, D-12, D-13, D-15, D-16, D-18, D-21, A-45 (also named Compound no. 1), 0-23, D-26 (also named Compound no. 5), AA-13 (also named Compound no. 2), AA-14, AA-15, A-66 (also named Compound no. 3), AA-5, AA-6, AA-12 (also named Compound no. 4), A-167, A-5, A-49, A-Si, A-59, A-70, A-34, A-35, A-26, A-71, A-64, A-65, A-67, A-69, A-79, A-99, A-i00, A-i0i, A-141, A-142, A-149, A-144, A-154, A-155, A-158, 8.007, 8.049, 8.056, 14.055, 14.056, 14.058, 14.059, 14.060, 14.073, 17.035, 17.059, 17.065, 17.066, 17.071, 17.074, 17.084, 18.049, 18.058, 18.060, 20.049, 20.052, 20.055, 20.056, 20.058, 20.059 or 20.060, whose structures are shown below; or an agriculturally acceptable salt thereof:

I

(A-4) (D-7) (0-8)

CI

(0-12) (0-13) (D-15) 16) ci ci (0-18) (D-21) _ 0 0 0 > Os 0 0 /\ >(>=o& 0 0 /B r\/-1 aO aO / / o aB a MB m -pfl) oW / C, 0B -(p

-

a -a a a p p p p ->K/° /0 0-> > o-o o-o 01 a) 0 / o P p P P P / / 0-> >Ko 0 /\ 00 00 o 00 2a / 0 0 >( )_o a0 ft rn 0 0 0 o 0 0 0 0 0 0 0 0 >oy >oc >oc oc 0c ::: 0 0 0 0 0 0 0 0 o o o o o 01=0

I I H H-

F F

/ )( )=o)( )=o)( )=o --C)

I mm 90

I I H-H- o-

%5' o Th >( >=o)( )=o --(_) I001I

I IIcI

(20.060) The above-shown preferred compounds of formula (I) have been disclosed before, e.g. in WO 2008/071405 Al, WO 2010/136431 A9, WO 201 1/073615 A2, and/orWO 2011/073616 A2. The above-shown compound numbers are generally the same as the compound numbers previously disclosed in WO 2008/071405 Al for the same compounds. For example, compound numbersA-4, 0-7, D-8, D-12, 0-13, 0-15, D-16, D-18, D-2l, A-45 (also named Compound no. 1 herein), 0-23, 0-26 (also named Compound no. 5 herein), A-66 (also named Compound no. 3 herein), A-167, A-5, A-49, A-51, A-59, A-70, A-34, A-35, A-26, A-71, A-64, A-65, A-67, A-69, A-79, A-99, A-l00, A-l0l, A-141, A-142, A-149, A-144, A-154, A-l55 and A-158, as shown hereinabove, are disclosed as specific example compounds in wa 2008/071405 Al within Table A (pages 87-109) or Table D (pages 227-233) of WO 2008/071405 Al; they are disclosed in wa 2008/071405 Al under the same "A" compound numbers and together with physical data, usually 1H nuclear magnetic resonance (NMR) data; some herbicidal data is also disclosed in WO 2008/071405 Al for most but not all of these compounds. Compound numbers 8.007, 8.049, 8.056, 14.055, 14.056, 14.058, 14.059, 14.060, 14.073, 17.035, 17.059, 17.065, 17.066, 17.071, 17.074, 17.084, 18.049, 18.058, 18.060, 20.049, 20.052, 20.055, 20.056, 20.058, 20.059 or 20.060, as shown herein, are disclosed in Tables 8, 14, 17, 18 and 20 of WO 2008/071405 Al which are cross-referenced to the relevant outer-phenyl substituent patterns disclosed in Table 1 of WO 2008/071405 Al. Finally, the "AA" compound numbers shown above generally correspond numerically to the "A" compound numbers previously disclosed in either WO 2011/073615 A2 or WO 2011/073616 A2 for the same compounds.

More preferably, in all aspects of the invention, the compound of formula (I) or the agriculturally acceptable salt thereof comprises (preferably is): one of the following compounds: A-4, D-7, D-8, D-12, D-13, D-15, D-16, D-18, D-21, A-45 (also named Compound no. 1), 0-23, 0-26 (also named Compound no. 5), AA-13 (also named Compound no. 2), AA-14, AA-15, A-66 (also named Compound no. 3), AA-5, AA-6, -20 -AA-12 (also named Compound no. 4), A-167, A-5, A-49, A-51, A-59, A-70, A-26, A-64, A-65, A-69, A-99, A-141, A-142, A-154, A-158, 14.059, 17.066, 17.071, 17.074, 18.049, 20.049, 20.052, 20.055, 20.056, 20.058, 20.059 or 20.060, whose structures are shown herein; or an agriculturally acceptable salt thereof.

Even more preferably, in all aspects of the invention, the compound of formula (I) or the agriculturally acceptable salt thereof comprises (preferably is): one of the following compounds: A-4, A-45 (also named Compound no. 1), D-26 (also named Compound no. 5), AA-13 (also named Compound no. 2), A-66 (also named Compound no. 3), AA-12 (also named Compound no. 4), A-167, A-26, A-64, A-65, A-69, A-99, A-158, 14.059, 20.049 or 20.056, whose structures are shown herein; or an agriculturally acceptable salt thereof.

Particularly preferably, in all aspects of the invention, the compound of formula (I) or the agriculturally acceptable salt thereof is a compound of formula (IA) or a compound of formula (IB) or an agriculturally acceptable salt of either of these: (IA) (IB), wherein, in formula (IA), R1 is ethyl or cyclopropyl, and R2A is hydrogen, chlorine or fluorine.

Most preferably, in all aspects or embodiments of the invention, in formula (IA), R is chlorine or fluorine.

Within a compound of formula (I) in which G = H (e.g. the compound of formula (IA)), the C-H of the pyrandione ring-carbon which is bonded to the biphenyl and which is between the two ketones, is acidic. Therefore, the agriculturally acceptable salt of the compound of formula (IA) can, for example, be an agriculturally acceptable base addition salt such as an -21 -alkali metal (e.g. sodium, potassium or lithium) salt, alkaline earth (e.g. calcium or magnesium) salt, ammonium salt, or a tetraC1-C4alkylammonium (e.g. tetramethylammonium, tetra-ethyl-ammonium or tetra-n-butylammonium) salt thereof. For example, the anion of the base addition salt of the compound of formula (IA) may, for example, have the following structure, where the negative charge is delocalized over the two diones and over the biphenyl: Preferably, the compound of formula (I) (e.g. compound of formula (IA) or (IB)) is present as the free compound (e.g. as a substantially salt-free compound).

In the compound of formula (IA) or the salt thereof, in one preferred embodiment, R1 is ethyl.

In the compound of formula (IA) or the salt thereof, in an alternative preferred embodiment, R1 is cyclopropyl.

In the compound of formula (I) or the salt thereof, in the most preferred embodiment, the compound of formula (I) is a compound of formula (IA) wherein R1 is ethyl and R is chlorine. In this embodiment, which is most preferred, the compound of formula (I) (and (IA)) is: (named Compound no. 1) (also named A-45).

The above-shown compound has the following chemical name: 4-(2',4'-dichloro-4-ethylbiphenyl-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5 (4H,6I--dione. Still more preferably, this -22 - compound or the salt thereof is present as the free compound (e.g. as a substantially salt-free compound). For the purposes of the present patent application and invention, the above-shown compound, present as the free compound, is named Compound no. 1. This compound (e.g. as the enol ketone tautomer) was previously disclosed as compound A-45 in WO 2008/071405 Al, and as Example PlO within WO 2010/136431 A9, and can in general be synthesized using the methods of preparation disclosed in either of these publications.

In the compound of formula (I) or the salt thereof, in an alternative particularly preferred embodiment, the compound of formula (I) is a compound of formula (IA) wherein R1 is cyclopropyl and R is fluorine. In this embodiment, which is particularly preferred, the compound of formula (I) (and (IA)) is: Cl (named Compound no. 2) (also named AA-13).

The above-shown compound has the following chemical name: 4-(4'-chloro-4-cyclopropyl-2'-fluorobiphenyl-3-yl)-2,2,6, 6-tetramethyl-2H-pyran-3,5(4H,6/--dione. Still more preferably, this compound or the salt thereof is present as the free compound (e.g. as a substantially salt-free compound). For the purposes of the present patent application and invention, the above-shown compound, present as the free compound, is named Compound no. 2. This compound (e.g. as the enol ketone tautomer) was previously disclosed as Example P8 within WO 2010/1 36431 A9, and can in general be synthesized using the methods of preparation disclosed in either WO 2008/071405 Al or WO 2010/136431 A9. Compound no. 2 is also disclosed as compound A-13 in WO 2011/073616 A2 (and so in the present specification it is named compound AA-13).

In the compound of formula (I) or the salt thereof, in an alternative particular embodiment, the compound of formula (I) is a compound of formula (IA) wherein R1 is ethyl and R is fluorine.

In this embodiment, the compound of formula (I) is: -23 - (named Compound no. 3) (also named A-66).

Preferably, the above-shown compound or the salt thereof is present as the free compound (e.g. as a substantially salt-free compound). For the purposes of the present patent application and invention, the above-shown compound, present as the free compound, is named Compound no. 3. This compound (e.g. as the enol ketone tautomer) was previously disclosed as compound A-66 in WO 2008/071405 Al, and can in general be synthesized using the methods of preparation disclosed in either WO 2008/071405 Al or WO 2010/1 36431 A9.

In the compound of formula (I) or the salt thereof, in an alternative particular embodiment, the compound of formula (I) is a compound of formula (IA) wherein R1 is cyclopropyl and R2A is chlorine. In this embodiment, the compound of formula (I) is: cI (named Compound no. 4) (also named AA-12).

Preferably, the above-shown compound or the salt thereof is present as the free compound (e.g. as a substantially salt-free compound). For the purposes of the present patent application and invention, the above-shown compound, present as the free compound, is named Compound no. 4. This compound (e.g. as the enol ketone tautomer) was previously disclosed as Example P9 within WO 201 0/1 36431 A9, and can in general be synthesized using the methods of preparation disclosed in either WO 2008/071405 Al or WO 2010/136431 A9. Compound no. 4 is also disclosed as compound A-i 2 in WO 2011/073616 A2 (and so in the present specification it is named compound AA-12).

In the compound of formula (I) or the salt thereof, in an alternative particular embodiment, the compound of formula (I) is a compound of formula (IB): (IS) (named Compound no. 5) (also named D-26).

Preferably, the above-shown compound or the salt thereof is present as the free compound (e.g. as a substantially salt-free compound). For the purposes of the present patent application and invention, the above-shown compound, present as the free compound, is named Compound no. 5. This compound was previously disclosed as compound D-26 of WO 2008/071405 Al (see PCT page 231).

A compound of formula (I) in which G is hydrogen can be present as the first or the second of the two equilibrating tautomeric forms (e.g. as shown below for formula (IA)) oras a mixture of both tautomeric forms. A first tautomeric form is a cyclic dione, specifically a 4-substituted 2H-pyran-3,5(4H,6H)-dione, and a second tautomeric form is the corresponding cyclic enol ketone, specifically a 3-hydroxy-4-substituted-2H,6H-pyran-3-ene-5-one. The compound of formula (I), as used in the present invention, encompasses the first tautomeric form, the second tautomeric form, and a mixture of the first and second tautomeric forms. This tautomerism is shown below for the particularly preferred compounds of formula (IA), but this tautomerism applies in the same or corresponding way to all compounds of formula (I) in which G is hydrogen: Cl Cl So, for example, in formula (IA), when R1 is ethyl and R2A is chlorine, the compound of formula (I) is: -25 -ci / , which, in all aspects of the present invention, is alternatively or OH Ci additionally present as And, for example, when R1 is cyclopropyl and R is fluorine, the compound of formula (I) is: 0 F 0 H 5, which, in all aspects of the present invention, is alternatively or additionally present as Preferred or particular or optional embodiments for the component (b), the rice-suitable ALS inhibitor herbicide, are as follows.

In one particular embodiment, the rice-suitable ALS inhibitor herbicide is present as an agriculturally acceptable salt, more particularly present as an agriculturally acceptable base addition salt such as an alkali metal (e.g. sodium, potassium or lithium) salt. This is preferable for bispyribac and/or trifloxysulfuron. Preferably, bispyribac is present as an agriculturally acceptable base addition salt such as an alkali metal (e.g. sodium, potassium or lithium, preferably sodium) salt thereof, more preferably bispyribac-sodium. Preferably, trifloxysulfuron is present as an agriculturally acceptable base addition salt such as an alkali metal (e.g. sodium, potassium or lithium, preferably sodium) salt thereof, more preferably trifloxysulfuron-sodium.

In an alternative particular embodiment, the rice-suitable ALS inhibitor herbicide is present as the free compound (e.g. as a substantially salt-free compound). This is preferable for -26 -bensulfuron-methyl, pyrazosulfuron-ethyl, azimsulfuron, flucetosulfuron, orthosulfamuron, prosulfuron, triasulfuron, pyriminobac-methyl, pyribenzoxim, and/or penoxsulam.

Among the rice-suitable ALS inhibitor herbicides are: -the following su/fonyl urea herbicides: bensulfuron-methyl, pyrazosulfuron-ethyl, azimsulfuron, flucetosulfuron, orthosulfamuron, prosulfuron, triasulfuron, and/or trifloxysulfuron, or an agriculturally acceptable salt of any of these, -the following pyrimidinyl (thio or oxy) benzoate herbicides: bispyribac, pyriminobac-methyl, and/or pyribenzoxim, or an agriculturally acceptable salt of any of these, and/or -the following triazolopyrimidine herbicide: penoxsulam or an agriculturally acceptable salt thereof.

In one preferred embodiment (bi), the rice-suitable ALS inhibitor herbicide is one of the above-listed sulfonyl urea herbicides.

Within this sulfonyl urea class (bi), more preferably, the rice-suitable ALS inhibitor herbicide is bensulfuron-methyl, pyrazosulfuron-ethyl, azimsulfuron, flucetosulfuron, and/or orthosulfamuron, or an agriculturally acceptable salt of any of these.

Most preferably, the rice-suitable ALS inhibitor herbicide is bensulfuron-methyl and/or pyrazosulfuron-ethyl, or an agriculturally acceptable salt of either of these. These two, when combined with the compound of formula (I), are associated with reduced phytotoxicity on rice e.g. transplanted rice (see Biological Example 3 hereinafter).

In an alternative also-preferred embodiment (b2), the rice-suitable ALS inhibitor herbicide is (a) one of the above-listed pyrimidinyl (thio or oxy) benzoate herbicides, or is (b) penoxsulam or an agriculturally acceptable salt thereof.

Within this (b2) class, more preferably, the rice-suitable ALS inhibitor herbicide is bispyribac and/or penoxsulam, or an agriculturally acceptable salt of either of these. These two are also regarded as excellent and suitable mixture partners for the compound of formula (I).

-27 -Considering the whole class overall [(bi) + (b2)], more preferably, the rice-suitable ALS inhibitor herbicide is bensulfuron-methyl, pyrazosulfuron-ethyl, bispyribac, and/or penoxsulam, or an agriculturally acceptable salt of any of these.

Particularly preferably, the rice-suitable ALS inhibitor herbicide is bensulfuron-methyl or an agriculturally acceptable salt thereof.

In all aspects or embodiments of the invention, preferably, if bensulfuron-methyl or a salt thereof is present, then the weight ratio of the compound of formula (I) or the salt thereof (e.g. Compound no. 1 or 2, or a salt thereof), calculated as the free compound, to the bensulfuron-methyl or the salt thereof, calculated as the free compound, is from 140:30 to 25:90, orfrom 120:30to30:90, ormorepreferablyisfrom 120:40to40:70, orfrom 120:40to 45:70, ormostpreferablyis 105:45to70:65, orfrom 105:45to75:65.

Particularly preferably, the rice-suitable ALS inhibitor herbicide is pyrazosulfuron-ethyl or an agriculturally acceptable salt thereof.

In all aspects or embodiments of the invention, preferably, if pyrazosulfuron-ethyl or a salt thereof is present, then the weight ratio of the compound of formula (I) or the salt thereof (e.g. Compound no. 1 or 2, or a salt thereof), calculated as the free compound, to the pyrazosulfuron-ethyl or the salt thereof, calculated as the free compound, is from 140:10 to 25:50, or from 120:10 to 30:50, or more preferably from 120:10 to 40:40, or from 120:15 to 45:30, or most preferably is from 105:15 to 70:30, or from 105:15 to 75:30.

In all aspects or embodiments of the invention, preferably, if azimsulfuron or a salt thereof is present, then the weight ratio of the compound of formula (I) or the salt thereof (e.g. Compound no. 1 or 2, or a salt thereof), calculated as the free compound, to the azimsulfuron or the salt thereof, calculated as the free compound, is from 140:10 to 25:40, or from 120:10 to 30:40, or more preferably is from 120:15 to 40:30, or from 120:15 to 45:30, or most preferably is from 105:20 to 70:25, or from 105:20 to 75:25.

In all aspects or embodiments of the invention, preferably, if flucetosulfuron or a salt thereof is present, then the weight ratio of the compound of formula (I) or the salt thereof (e.g. Compound no. 1 or 2, or a salt thereof), calculated as the free compound, to the flucetosulfuron or the salt thereof, calculated as the free compound, is from 140:10 to 25:50, -28 -or from 120:10 to 30:50, or is more preferably from 120:15 to 40:40, or from 120:15 to 45:40, or is most preferably from from 105:20 to 70:30, or from 105:20 to 75:30.

In all aspects or embodiments of the invention, preferably, if orthosulfamuron or a salt thereof is present, then the weight ratio of the compound of formula (I) or the salt thereof (e.g. Compound no. 1 or 2, or a salt thereof), calculated as the free compound, to the orthosulfamuron or the salt thereof, calculated as the free compound, is 140:20 to 25:100, or from 120:20 to 30:100, or is more preferably from 120:25 to 40:75, or from 120:25 to 45:75, or is most preferably from 105:40 to 70:75, or from 105:40 to 75:75.

In all aspects or embodiments of the invention, preferably, if prosulfuron or a salt thereof is present, then the weight ratio of the compound of formula (I) or the salt thereof (e.g. Compound no. 1 or 2, or a salt thereof), calculated as the free compound, to the prosulfuron or the salt thereof, calculated as the free compound, is from 140:5 to 25:50, or from 120:5 to 30:50, or is more preferably from 120:7 to 40:40, or from 120:7 to 45:40, or is most preferably from 105:12 to 70:30, or from 105:12 to 75:30.

In all aspects or embodiments of the invention, preferably, if triasulfuron or a salt thereof is present, then the weight ratio of the compound of formula (I) or the salt thereof (e.g. Compound no. 1 or 2, or a salt thereof), calculated as the free compound, to the triasulfuron or the salt thereof, calculated as the free compound, is from 140:2 to 25:15, or from 120:2 to 30:15, or is more preferably from 120:3 to 40:10, or from 120:3 to 45:10, or is most preferably from 105:5 to 70:10, or from 105:5 to 75:10.

In all aspects or embodiments of the invention, preferably, if trifloxysulfuron or a salt thereof is present, then the weight ratio of the compound of formula (I) or the salt thereof (e.g. Compound no. 1 or 2, or a salt thereof), calculated as the free compound, to the trifloxysulfuron or the salt thereof, calculated as the free compound, is from 140:2 to 25:80, or from 120:2 to 30:80, or is more preferably from 120:3 to 40:70, or from 120:3 to 45:70, or is most preferably from 105:5 to 70:65, or from 105:5 to 75:65.

Particularly preferably, the rice-suitable ALS inhibitor herbicide is bispyribac or an agriculturally acceptable salt thereof, more preferably bispyribac or an agriculturally acceptable base addition salt thereof, still more preferably an agriculturally acceptable base addition salt of bispyribac, such as an alkali metal (e.g. lithium, sodium or potassium) salt of bispyribac, most preferably a or the sodium salt of bispyribac (i.e. bispyribac-sodium).

-29 -In all aspects or embodiments of the invention, preferably, if bispyribac or a salt thereof is present, then the weight ratio of the compound of formula (I) or the salt thereof (e.g. Compound no. 1 or 2, or a salt thereof), calculated as the free compound, to the bispyribac or the salt thereof, calculated as the free compound, is preferably from 140:15 to 25:50, or from 120:15 to 30:50, or more preferably from 120:20 to 40:40, or from 120:20 to 45:40, or most preferably from 105:25 to 70:35, or from 105:25 to 75:35.

In all aspects or embodiments of the invention, preferably, if pyriminobac-methyl or a salt thereof is present, then the weight ratio of the compound of formula (I) or the salt thereof (e.g. Compound no. 1 or 2, or a salt thereof), calculated as the free compound, to the pyriminobac-methyl or the salt thereof, calculated as the free compound, is from 140:15 to 25:150, or from 120:15 to 30:150, or is more preferably from 120:20 to 40:140, or from 120:20 to 45:140, or is most preferably from 105:30 to 70:120, or from 105:30 to 75:120.

In all aspects or embodiments of the invention, preferably, if pyribenzoxim or a salt thereof is present, then the weight ratio of the compound of formula (I) or the salt thereof (e.g. Compound no. 1 or 2, or a salt thereof), calculated as the free compound, to the pyribenzoxim or the salt thereof, calculated as the free compound, is preferably from 140:15 to 25:50, or from 120:15 to 30:50, or is more preferably from 120:20 to 40:40, or from 120:20 to 45:40, or is most preferably from 105:30 to 70:30, or from 105:30 to 75:30.

Particularly preferably, the rice-suitable ALS inhibitor herbicide is penoxsulam or an agriculturally acceptable salt thereof.

In all aspects or embodiments of the invention, preferably, if penoxsulam or a salt thereof is present, then the weight ratio of the compound of formula (I) or the salt thereof (e.g. Compound no. 1 or 2, or a salt thereof), calculated as the free compound, to the penoxsulam or the salt thereof, calculated as the free compound, is from 140:4 to 25:50, or from 120:4 to 30:50, or more preferably from 120:10 to 40:40, or from 120:10 to 45:40, or most preferably from 105:15 to 70:30, or from 105:15 to 75:30.

Particular mixtures or combinations that can be used in the herbicidal composition -30 -In a preferred embodiment of all aspects of the invention, a herbicidal composition of the invention comprises one of the following mixtures or combinations of (a) the compound of formula (I) or a salt thereof, and (b) the ALS (acetolactate synthase) inhibitor herbicide suitable for use on rice. In these preferred compositons or mixtures or combinations listed below, the numbers of the compounds of formula (I) (e.g. compoundsA-4, D-7, D-8, D-12, D- 13, D-15, D-16, D-18, D-21, A-45 (also named Compound no. 1), D-23, D-26 (also named Compound no. 5), AA-13 (also named Compound no. 2), AA-14, AA-15, A-66 (also named Compound no. 3), AA-5, AA-6, AA-12 (also named Compound no. 4), A-167, A-5, A-49, A- 51, A-59, A-70, A-34, A-35, A-26, A-71, A-64, A-65, A-67, A-69, A-79, A-99, A-100, A-101, A- 141, A-142, A-149, A-144, A-154, A-155, A-158, 8.007, 8.049, 8.056, 14.055, 14.056, 14.058, 14.059, 14.060, 14.073, 17.035, 17.059, 17.065, 17.066, 17.071, 17.074, 17.084, 18.049, 18.058, 18.060, 20.049, 20.052, 20.055, 20.056, 20.058, 20.059 or 20.060) refer to the previously-mentioned preferred compounds of formula (I) whose structures are shown hereinabove: [pad/cu/arty preferred]: compound A-4 or salt + bensulfuron-methyl or salt, compound A-4 or salt + pyrazosulfuron-ethyl or salt, compound A-4 or salt + azimsulfuron or salt, compound A- 4 or salt + flucetosulfuron or salt, compound A-4 or salt + orthosulfamuron or salt, compound A-4 or salt + piosulfuron or salt, compound A-4 or salt + triasulfuron or salt, compound A-4 or salt + trifloxysulfuron or salt, compound A-4 or salt + bispyribac or salt (e.g. compound A-4 or salt + bispyribac-sodium or bispyribac-potassium), compound A-4 or salt + pyriminobac-methyl or salt, compound A-4 or salt + pyribenzoxim or salt, or compound A-4 or salt + penoxsulam or salt; or compound D-7 or salt + bensulfuron-methyl or salt, compound D-7 or salt + pyrazosulfuron-ethyl or salt, compound 0-7 or salt + azimsulfuron or salt, compound D-7 or salt + flucetosulfuron or salt, compound D-7 or salt ÷ orthosulfamuron or salt, compound D-7 or salt + prosulfuron or salt, compound D-7 or salt + triasulfuron or salt, compound 0-7 or salt + trifloxysulfuron or salt, compound 0-7 or salt + bispyribac or salt (e.g. compound 0-7 or salt + bispyribac-sodium or bispyribac-potassium), compound 0-7 or salt + pyriminobac-methyl or salt, compound 0-7 or salt + pyribenzoxim or salt, or compound 0-7 or salt + penoxsulam or salt; or -31 - compound D-8 or salt + bensulfuron-methyl or salt, compound D-8 or salt + pyrazosulfuron-ethyl or salt, compound 0-8 or salt + azimsulfuron or salt, compound D-8 or salt + flucetosulfuron or salt, compound D-8 or salt + orthosulfamuron or salt, compound D-8 or salt + prosulfuron or salt, compound D-8 or salt + triasulfuron or salt, compound 0-8 or salt + trifloxysulfuron or salt, compound D-8 or salt ÷ bispyribac or salt (e.g. compound D-8 or salt + bispyribac-sodium or bispyribac-potassium), compound 0-8 or salt + pyriminobac-methyl or salt, compound 0-8 or salt + pyribenzoxim or salt, or compound 0-8 or salt + penoxsulam or salt; or compound D-12 orsalt+ bensulfuron-methyl or salt, compound D-12 orsalt+ pyrazosulfuron-ethyl or salt, compound 0-12 or salt + azimsulfuron or salt, compound D-12 or salt + flucetosulfuron or salt, compound D-12 or salt + orthosulfamuron or salt, compound D-12 or salt + prosulfuron or salt, compound D-12 or salt + triasulfuron or salt, compound 0- 12 or salt + trifloxysulfuron or salt, compound D-12 or salt + bispyribac or salt (e.g. compound D-12 or salt + bispyribac-sodium or bispyribac-potassium), compound D-12 or salt + pyriminobac-methyl or salt, compound D-12 or salt + pyribenzoxim or salt, or compound D- 12 or salt + penoxsulam or salt; or compound D-13 or salt + bensulfuron-methyl or salt, compound D-13 or salt + pyrazosulfuron-ethyl or salt, compound D-13 or salt + azimsulfuron or salt, compound D-13 or salt + flucetosulfuron or salt, compound D-13 or salt + orthosulfamuron or salt, compound D-13 or salt + prosulfuron or salt, compound 0-13 or salt + triasulfuron or salt, compound 0- 13 or salt + trifloxysulfuron or salt, compound D-13 or salt + bispyribac or salt (e.g. compound D-13 or salt + bispyribac-sodium or bispyribac-potassium), compound 0-13 or salt + pyriminobac-methyl or salt, compound 0-13 or salt + pyribenzoxim or salt, or compound D- 13 or salt + penoxsulam or salt; or compound 0-15 or salt + bensulfuron-methyl or salt, compound 0-15 or salt + pyrazosulfuron-ethyl or salt, compound D-15 or salt + azimsulfuron or salt, compound D-15 or salt + flucetosulfuron or salt, compound 0-15 or salt + orthosulfamuron or salt, compound D-15 or salt + prosulfuron or salt, compound D-15 or salt + triasulfuron or salt, compound 0-or salt + trifloxysulfuron or salt, compound D-15 or salt + bispyribac or salt (e.g. compound D-15 or salt + bispyribac-sodium or bispyribac-potassium), compound D-15 or salt -32 - + pyriminobac-methyl or salt, compound D-15 or salt + pyribenzoxim or salt, or compound D-or salt + penoxsulam or salt; or compound 0-16 or salt + bensulfuron-methyl or salt, compound 0-16 or salt + pyrazosulfuron-ethyl or salt, compound D-16 or salt + azimsulfuron or salt, compound D-16 or salt + flucetosulfuron or salt, compound 0-16 or salt + orthosulfamuron or salt, compound D-16 or salt + prosulfuron or salt, compound D-16 or salt + triasulfuron or salt, compound 0- 16 or salt + trifloxysulfuron or salt, compound D-16 or salt + bispyribac or salt (e.g. compound 0-16 or salt + bispyribac-sodium or bispyribac-potassium), compound 0-16 or salt + pyriminobac-methyl or salt, compound 0-16 or salt + pyribenzoxim or salt, or compound D- 16 or salt + penoxsulam or salt; or compound D-18 or salt + bensulfuron-methyl or salt, compound D-18 or salt + pyrazosulfuron-ethyl or salt, compound 0-18 or salt + azimsulfuron or salt, compound D-18 or salt + flucetosulfuron or salt, compound D-18 or salt + orthosulfamuron or salt, compound D-18 or salt + prosulfuron or salt, compound D-18 or salt ÷ triasulfuron or salt, compound D- 18 or salt + trifloxysulfuron or salt, compound 0-18 or salt + bispyribac or salt (e.g. compound 0-18 or salt + bispyribac-sodium or bispyribac-potassium), compound 0-18 or salt + pyriminobac-methyl or salt, compound 0-18 or salt + pyribenzoxim or salt, or compound D- 18 or salt + penoxsulam or salt; or compound 0-21 or salt + bensulfuron-methyl or salt, compound 0-21 or salt + pyrazosulfuron-ethyl or salt, compound 0-21 or salt + azimsulfuron or salt, compound D-21 or salt + flucetosulfuron or salt, compound 0-21 or salt + orthosulfamuron or salt, compound D-21 or salt + prosulfuron or salt, compound 0-21 or salt + triasulfuron or salt, compound 0- 21 or salt + trifloxysulfuron or salt, compound 0-21 or salt + bispyribac or salt (e.g. compound 0-21 or salt + bispyribac-sodium or bispyribac-potassium), compound 0-21 or salt + pyriminobac-methyl or salt, compound 0-21 or salt + pyribenzoxim or salt, or compound 0- 21 or salt + penoxsulam or salt; or [particularly preferred]: compound A-45 (Compound no. 1) or salt + bensulfuron-methyl or salt, compound A-45 (Compound no. 1) or salt + pyrazosulfuron-ethyl or salt, compound A- (Compound no. 1) or salt + azimsulfuron or salt, compound A-45 (Compound no. 1) or salt + flucetosulfuron or salt, compound A-45 (Compound no. 1) or salt + orthosulfamuron or salt, -33 -compound A-45 (Compound no. 1) or salt + prosulfuron or salt, compound A-45 (Compound no. 1) or salt + triasulfuron or salt, compound A-45 (Compound no. 1) or salt + trifloxysulfuron or salt, compound A-45 (Compound no. 1) or salt + bispyribac or salt (e.g. compound A-45 (Compound no. 1) or salt + bispyribac-sodiurn or bispyribac-potassium), compound A-45 (Compound no. 1) or salt + pyriminobac-methyl or salt, compound A-45 (Compound no. 1) or salt + pyribenzoxim or salt, or compound A-45 (Compound no. 1) or salt + penoxsulam or salt; or compound D-23 or salt + bensulfuron-methyl or salt, compound D-23 or salt + pyrazosulfuron-ethyl or salt, compound 0-23 or salt + azimsulfuron or salt, compound D-23 or salt + flucetosulfuron or salt, compound 0-23 or salt + orthosulfamuron or salt, compound D-23 or salt + prosulfuron or salt, compound D-23 or salt ÷ triasulfuron or salt, compound D- 23 or salt + trifloxysulfuron or salt, compound D-23 or salt + bispyribac or salt (e.g. compound D-23 or salt + bispyribac-sodium or bispyribac-potassium), compound D-23 or salt + pyriminobac-methyl or salt, compound D-23 or salt + pyribenzoxim or salt, or compound D- 23 or salt + penoxsulam or salt; or [particularly preferred]: compound D-26 (Compound no. 5) or salt + bensulfuron-methyl or salt, compound 0-26 (Compound no. 5) or salt + pyrazosulfuron-ethyl or salt, compound D- 26 (Compound no. 5) or salt + azimsulfuron or salt, compound D-26 (Compound no. 5) or salt + flucetosulfuron or salt, compound D-26 (Compound no. 5) or salt + orthosulfamuron or salt, compound 0-26 (Compound no. 5) or salt + prosulfuron or salt, compound 0-26 (Compound no. 5) or salt + triasulfuron or salt, compound D-26 (Compound no. 5) or salt + trifloxysulfuron or salt, compound 0-26 (Compound no. 5) or salt + bispyribac or salt (e.g. compound D-26 (Compound no. 5) or salt + bispyribac-sodium or bispyribac-potassium), compound D-26 (Compound no. 5) or salt + pyriminobac-methyl or salt, compound D-26 (Compound no. 5) or salt + pyribenzoxim or salt, or compound D-26 (Compound no. 5) or salt + penoxsulam or salt; or [particularly preferred]: compound AA-13 (Compound no. 2) or salt + bensulfuron-methyl 01 salt, compound AA-13 (Compound no. 2) or salt + pyrazosulfuron-ethyl or salt, compound AA-13 (Compound no. 2) or salt + azimsulfuron or salt, compound AA-13 (Compound no. 2) or salt + flucetosulfuron or salt, compound AA-13 (Compound no. 2) or salt + orthosulfamuron or salt, compound AA-13 (Compound no. 2) or salt + prosulfuron or salt, -34 -compound AA-13 (Compound no. 2) or salt + triasulfuron or salt, compound AA-13 (Compound no. 2) or salt + trifloxysulfuron or salt, compound AA-13 (Compound no. 2) or salt + bispyribac or salt (e.g. compound AA-13 (Compound no. 2) or salt + bispyribac-sodium or bispyribac-potassium), compound AA-13 (Compound no. 2) or salt + pyriminobac-methyl or salt, compound AA-13 (Compound no. 2) or salt + pyribenzoxim or salt, or compound AA- 13 (Compound no. 2) or salt + penoxsulam or salt; or compound AA-14 or salt + bensulfuron-methyl or salt, compound AA-14 or salt + pyrazosulfuron-ethyl or salt, compound AA-14 or salt + azimsulfuron or salt, compound AA- 14 or salt + flucetosulfuron or salt, compound AA-14 or salt + orthosulfamuron or salt, compound AA-14 or salt + prosulfuron or salt, compound AA-14 or salt + triasulfuron or salt, compound AA-14 or salt + trifloxysulfuron or salt, compound AA-14 or salt + bispyribac or salt (e.g. compound AA-14 or salt + bispyribac-sodium or bispyribac-potassium), compound AA-14 or salt + pyriminobac-methyl or salt, compound AA-14 or salt÷ pyribenzoxim or salt, or compound AA-14 or salt + penoxsulam or salt; or compound AA-15 or salt + bensulfuron-methyl or salt, compound AA-15 or salt + pyrazosulfuron-ethyl or salt, compound AA-15 or salt + azimsulfuron or salt, compound AA-or salt + flucetosulfuron or salt, compound AA-15 or salt + orthosulfamuron or salt, compound AA-15 or salt + prosulfuron or salt, compound AA-15 or salt + triasulfuron or salt, compound AA-15 or salt + trifloxysulfuron or salt, compound AA-15 or salt + bispyribac or salt (e.g. compound AA-15 or salt + bispyribac-sodium or bispyribac-potassium), compound AA-15 or salt + pyriminobac-methyl or salt, compound AA-15 or salt+ pyribenzoxim or salt, or compound AA-15 or salt + penoxsulam or salt; or [particularly preferred]: compound A-66 (Compound no. 3) or salt + bensulfuron-methyl or salt, compound A-SB (Compound no. 3) or salt + pyrazosulfuron-ethyl or salt, compound A- 66 (Compound no. 3) or salt + azimsulfuron or salt, compound A-66 (Compound no. 3) or salt + flucetosulfuron or salt, compound A-66 (Compound no. 3) or salt + orthosulfamuron or salt, compound A-66 (Compound no. 3) or salt + prosulfuron or salt, compound A-66 (Compound no. 3) or salt + triasulfuron or salt, compound A-66 (Compound no. 3) or salt + trifloxysulfuron or salt, compound A-66 (Compound no. 3) or salt + bispyribac or salt (e.g. compound A-66 (Compound no. 3) or salt + bispyribac-sodiurii or bispyribac-potassium), compound A-66 (Compound no. 3) or salt + pyriminobac-methyl or salt, compound A-66 (Compound no. 3) or -35 -salt + pyribenzoxim or salt, or compound A-66 (Compound no. 3) or salt + penoxsulam or salt; or compound AA-5 or salt + bensulfuron-methyl or salt, compound AA-5 or salt + pyrazosulfuron-ethyl or salt, compound AA-5 or salt + azimsulfuron or salt, compound AA-5 or salt + flucetosulfuron or salt, compound AA-5 or salt ÷ orthosulfamuron or salt, compound AA-5 or salt + prosulfuron or salt, compound AA-5 or salt + triasulfuron or salt, compound AA-5 or salt + trifloxysulfuron or salt, compound AA-5 or salt + bispyribac or salt (e.g. compound AA-5 or salt + bispyribac-sodium or bispyribac-potassium), compound AA-5 or salt + pyriminobac-methyl or salt, compound AA-5 or salt + pyribenzoxim or salt, or compound AA-5 or salt + penoxsulam or salt; or compound AA-6 or salt + bensulfuron-methyl or salt, compound AA-6 or salt + pyrazosulfuron-ethyl or salt, compound AA-6 or salt + azimsulfuron or salt, compound AA-6 or salt + flucetosulfuron or salt, compound AA-6 or salt + orthosulfamuron or salt, compound AA-6 or salt + prosulfuron or salt, compound AA-6 or salt + triasulfuron or salt, compound AA-6 or salt + trifloxysulfuron or salt, compound AA-6 or salt + bispyribac or salt (e.g. compound AA-6 or salt + bispyribac-sodium or bispyribac-potassium), compound AA-6 or salt + pyriminobac-methyl or salt, compound AA-6 or salt + pyribenzoxim or salt, or compound AA-6 or salt + penoxsulam or salt; or [particularly preferred]: compound AA-12 (Compound no. 4) or salt + bensulfuron-methyl or salt, compound AA-12 (Compound no. 4) or salt + pyrazosulfuron-ethyl or salt, compound AA-12 (Compound no. 4) or salt + azimsulfuron or salt, compound AA-12 (Compound no. 4) or salt + flucetosulfuron or salt, compound AA-12 (Compound no. 4) or salt + orthosulfamuron or salt, compound AA-12 (Compound no. 4) or salt + prosulfuron or salt, compound AA-12 (Compound no. 4) or salt + triasulfuron or salt, compound AA-12 (Compound no. 4) or salt + trifloxysulfuron or salt, compound AA-12 (Compound no. 4) or salt + bispyribac or salt (e.g. compound AA-12 (Compound no. 4) or salt + bispyribac-sodium or bispyribac-potassium), compound AA-12 (Compound no. 4) or salt + pyrirninobac-methyl or salt, compound AA-12 (Compound no. 4) or salt + pyribenzoxim or salt, or compound AA- 12 (Compound no. 4) or salt + penoxsulam or salt; or -36 - [particularly preferred]: compound A-167 or salt + bensulfuron-methyl or salt, compound A- 167 or salt + pyrazosulfuron-ethyl or salt, compound A-167 or salt + azimsulfuron or salt, compound A-167 or salt + flucetosulfuron or salt, compound A-167 or salt + orthosulfamuron or salt, compound A-167 or salt + prosulfuron or salt, compound A-167 or salt + triasulfuron S or salt, compound A-167 or salt + trifloxysulfuron or salt, compound A-167 or salt + bispyribac or salt (e.g. compound A-167 or salt + bispyribac-sodium or bispyribac-potassium), compound A-167 or salt + pyriminobac-methyl or salt, compound A-167 or salt + pyribenzoxim or salt, or compound A-167 or salt + penoxsulam or salt; or compound A-S or salt + bensulfuron-methyl or salt, compound A-5 or salt + pyrazosulfuron-ethyl or salt, compound A-5 or salt + azimsulfuron or salt, compound A-5 or salt + flucetosulfuron or salt, compound A-S or salt ÷ orthosulfamuron or salt, compound A-S or salt + prosulfuron or salt, compound A-5 or salt + triasulfuron or salt, compound A-5 or salt + trifloxysulfuron or salt, compound A-5 or salt + bispyribac or salt (e.g. compound A-S or salt + bispyribac-sodium or bispyribac-potassium), compound A-S or salt + pyriminobac-methyl or salt, compound A-S or salt + pyribenzoxim or salt, or compound A-S or salt + penoxsulam or salt; or compound A-49 or salt + bensulfuron-methyl or salt, compound A-49 or salt + pyrazosulfuron-ethyl or salt, compound A-49 or salt + azimsulfuron or salt, compound A-49 or salt + flucetosulfuron or salt, compound A-49 or salt + orthosulfamuron or salt, compound A- 49 or salt + prosulfuron or salt, compound A-49 or salt + triasulfuron or salt, compound A-49 or salt + trifloxysulfuron or salt, compound A-49 or salt + bispyribac or salt (e.g. compound A- 49 or salt + bispyribac-sodium or bispyribac-potassium), compound A-49 or salt + pyriminobac-methyl or salt, compound A-49 or salt + pyribenzoxim or salt, or compound A-49 or salt + penoxsulam or salt; or compound A-51 or salt + bensulfuron-methyl or salt, compound A-Si or salt + pyrazosulfuron-ethyl or salt, compound A-Si or salt + azimsulfuron or salt, compound A-Si or salt + flucetosulfuron or salt, compound A-51 or salt + orthosulfamuron or salt, compound A-Si or salt + prosulfuron or salt, compound A-Si or salt + triasulfuron or salt, compound A-Si or salt + trifloxysulfuron or salt, compound A-Si or salt + bispyribac or salt (e.g. compound A-Si or salt + bispyribac-sodium or bispyribac-potassium), compound A-Si or salt + -37 -pyriminobac-methyl or salt, compound A-Si or salt + pyribenzoxim or salt, or compound A-Si or salt + penoxsulam or salt; or compound A-59 or salt + bensulfuron-methyl or salt, compound A-59 or salt + pyrazosulfuron-ethyl or salt, compound A-59 or salt + azimsulfuron or salt, compound A-59 or salt + flucetosulfuron or salt, compound A-59 or salt + orthosulfamuron or salt, compound A- 59 or salt + prosulfuron or salt, compound A-59 or salt + triasulfuron or salt, compound A-59 or salt + trifloxysulfuron or salt, compound A-59 or salt + bispyribac or salt (e.g. compound A- 59 or salt + bispyribac-sodium or bispyribac-potassium), compound A-59 or salt + pyriminobac-methyl or salt, compound A-59 or salt + pyribenzoxim or salt, or compound A-59 or salt + penoxsulam or salt; or compound A-70 or salt + bensulfuron-methyl or salt, compound A-70 or salt + pyrazosulfuron-ethyl or salt, compound A-70 or salt + azimsulfuron or salt, compound A-70 or salt + flucetosulfuron or salt, compound A-70 or salt + orthosulfamuron or salt, compound A-or salt + prosulfuron or salt, compound A-70 or salt + triasulfuron or salt, compound A-70 or salt + trifloxysulfuron or salt, compound A-70 or salt + bispyribac or salt (e.g. compound A-or salt + bispyribac-sodium or bispyribac-potassium), compound A-70 or salt + pyriminobac-methyl or salt, compound A-70 or salt + pyribenzoxim or salt, or compound A-70 or salt + penoxsulam or salt; or compound A-34 or salt + bensulfuron-methyl or salt, compound A-34 or salt + pyrazosulfuron-ethyl or salt, compound A-34 or salt + azimsulfuron or salt, compound A-34 or salt + flucetosulfuron or salt, compound A-34 or salt + orthosulfamuron or salt, compound A- 34 or salt + prosulfuron or salt, compound A-34 or salt + triasulfuron or salt, compound A-34 or salt + trifloxysulfuron or salt, compound A-34 or salt + bispyribac or salt (e.g. compound A- 34 or salt + bispyribac-sodium or bispyribac-potassium), compound A-34 or salt + pyriminobac-methyl or salt, compound A-34 or salt + pyribenzoxim or salt, or compound A-34 or salt + penoxsulam or salt; or compound A-35 or salt + bensulfuron-methyl or salt, compound A-35 or salt + pyrazosulfuron-ethyl or salt, compound A-35 or salt + azimsulfuron or salt, compound A-35 or salt + flucetosulfuron or salt, compound A-35 or salt + orthosulfamuron or salt, compound A-or salt + prosulfuron or salt, compound A-35 or salt + triasulfuron or salt, compound A-35 -38 - or salt + trifloxysulfuron or salt, compound A-35 or salt + bispyribac or salt (e.g. compound A-or salt + bispyribac-sodium or bispyribac-potassium), compound A-35 or salt + pyriminobac-methyl or salt, compound A-35 or salt + pyribenzoxim or salt, or compound A-35 or salt + penoxsulam or salt; or [particularly preferred]: compound A-26 or salt + bensulfuron-methyl or salt, compound A-26 or salt + pyrazosulfuron-ethyl or salt, compound A-26 or salt + azimsulfuron or salt, compound A-26 or salt + flucetosulfuron or salt, compound A-26 or salt + orthosulfamuron or salt, compound A-26 or salt + prosulfuron or salt, compound A-26 or salt + triasulfuron or salt, compound A-26 or salt + trifloxysulfuron or salt, compound A-26 or salt + bispyribac or salt (e.g. compound A-26 or salt + bispyribac-sodium or bispyribac-potassium), compound A- 26 or salt + pyriminobac-methyl or salt, compound A-26 or salt ÷ pyribenzoxim or salt, or compound A-26 or salt + penoxsulam or salt; or compound A-71 or salt + bensulfuron-methyl or salt, compound A-71 or salt + pyrazosulfuron-ethyl or salt, compound A-71 or salt + azimsulfuron or salt, compound A-71 or salt + flucetosulfuron or salt, compound A-71 or salt + orthosulfamuron or salt, compound A- 71 or salt + prosulfuron or salt, compound A-71 or salt + triasulfuron or salt, compound A-71 or salt + trifloxysulfuron or salt, compound A-71 or salt + bispyribac or salt (e.g. compound A- 71 or salt + bispyribac-sodium or bispyribac-potassium), compound A-71 or salt + pyriminobac-methyl or salt, compound A-71 or salt + pyribenzoxim or salt, or compound A-71 or salt + penoxsulam or salt; or [particularly preferred]: compound A-64 or salt + bensulfuron-methyl or salt, compound A-64 or salt + pyrazosulfuron-ethyl or salt, compound A-64 or salt + azimsulfuron or salt, compound A-64 or salt + flucetosulfuron or salt, compound A-64 or salt + orthosulfamuron or salt, compound A-64 or salt + prosulfuron or salt, compound A-64 or salt + triasulfuron or salt, compound A-64 or salt + trifloxysulfuron or salt, compound A-64 or salt + bispyribac or salt (e.g. compound A-64 or salt + bispyribac-sodium or bispyribac-potassium), compound A- 64 or salt + pyriminobac-methyl or salt, compound A-64 or salt + pyribenzoxim or salt, or compound A-64 or salt + penoxsulam or salt; or [particularly preferred]: compound A-65 or salt + bensulfuron-methyl or salt, compound A-65 or salt + pyrazosulfuron-ethyl or salt, compound A-65 or salt + azimsulfuron or salt, -39 -compound A-65 or salt + flucetosulfuron or salt, compound A-65 or salt + orthosulfamuron or salt, compound A-65 or salt + prosulfuron or salt, compound A-65 or salt + triasulfuron or salt, compound A-65 or salt + trifloxysulfuron or salt, compound A-65 or salt + bispyribac or salt (e.g. compound A-65 or salt + bispyribac-sodium or bispyribac-potassium), compound A- 65 or salt + pyriminobac-methyl or salt, compound A-65 or salt ÷ pyribenzoxim or salt, or compound A-65 or salt + penoxsulam or salt; or compound A-67 or salt + bensulfuron-methyl or salt, compound A-67 or salt + pyrazosulfuron-ethyl or salt, compound A-67 or salt + azimsulfuron or salt, compound A-67 or salt + flucetosulfuron or salt, compound A-67 or salt + orthosulfamuron or salt, compound A- 67 or salt + prosulfuron or salt, compound A-67 or salt + triasulfuron or salt, compound A-67 or salt + trifloxysulfuron or salt, compound A-67 or salt + bispyribac or salt (e.g. compound A- 67 or salt + bispyribac-sodium or bispyribac-potassium), compound A-67 or salt + pyriminobac-methyl or salt, compound A-67 or salt + pyribenzoxim or salt, or compound A-67 or salt + penoxsulam or salt; or [particularly preferred]: compound A-69 or salt + bensulfuron-methyl or salt, compound A-69 or salt + pyrazosulfuron-ethyl or salt, compound A-69 or salt + azimsulfuron or salt, compound A-69 or salt + flucetosulfuron or salt, compound A-69 or salt + orthosulfamuron or salt, compound A-69 or salt + prosulfuron or salt, compound A-69 or salt + triasulfuron or salt, compound A-69 or salt + trifloxysulfuron or salt, compound A-69 or salt + bispyribac or salt (e.g. compound A-69 or salt + bispyribac-sodium or bispyribac-potassium), compound A- 69 or salt + pyriminobac-methyl or salt, compound A-69 or salt + pyribenzoxim or salt, or compound A-69 or salt + penoxsulam or salt; or compound A-79 or salt + bensulfuron-methyl or salt, compound A-79 or salt + pyrazosulfuron-ethyl or salt, compound A-79 or salt + azimsulfuron or salt, compound A-79 or salt + flucetosulfuron or salt, compound A-79 or salt + orthosulfamuron or salt, compound A- 79 or salt + prosulfuron or salt, compound A-79 or salt + triasulfuron or salt, compound A-79 or salt + trifloxysulfuron or salt, compound A-79 or salt + bispyribac or salt (e.g. compound A- 79 or salt + bispyribac-sodium or bispyribac-potassium), compound A-79 or salt + pyriminobac-methyl or salt, compound A-79 or salt + pyribenzoxim or salt, or compound A-79 or salt + penoxsulam or salt; or -40 - [particularly preferred]: compound A-99 or salt + bensulfuron-methyl or salt, compound A-99 or salt + pyrazosulfuron-ethyl or salt, compound A-99 or salt + azimsulfuron or salt, compound A-99 or salt + flucetosulfuron or salt, compound A-99 or salt + orthosulfamuron or salt, compound A-99 or salt + prosulfuron or salt, compound A-99 or salt + triasulfuron or salt, compound A-99 or salt + trifloxysulfuron or salt, compound A-99 or salt ÷ bispyribac or salt (e.g. compound A-99 or salt + bispyribac-sodium or bispyribac-potassium), compound A- 99 or salt + pyriminobac-methyl or salt, compound A-99 or salt + pyribenzoxim or salt, or compound A-99 or salt + penoxsulam or salt; or compound A-100 or salt + bensulfuron-methyl or salt, compound A-100 or salt + pyrazosulfuron-ethyl or salt, compound A-100 or salt + azimsulfuron or salt, compound A-100 or salt + flucetosulfuron or salt, compound A-lOU or salt + orthosulfamuron or salt, compound A-100 or salt + prosulfuron or salt, compound A-lao or salt + triasulfuron or salt, compound A-100 or salt + trifloxysulfuron or salt, compound A-l00 or salt + bispyribac or salt (e.g. compound A-lOU or salt + bispyribac-sodium or bispyribac-potassium), compound A-lOU or salt + pyriminobac-methyl or salt, compound A-100 or salt ÷ pyribenzoxim or salt, or compound A-100 or salt + penoxsulam or salt; or compound A-101 or salt + bensulfuron-methyl or salt, compound A-101 or salt + pyrazosulfuron-ethyl or salt, compound A-10l or salt + azimsulfuron or salt, compound A-l01 or salt + flucetosulfuron or salt, compound A-l01 or salt + orthosulfamuron or salt, compound A-101 or salt + prosulfuron or salt, compound A-l01 or salt + triasulfuron or salt, compound A-101 or salt + trifloxysulfuron or salt, compound A-l01 or salt + bispyribac or salt (e.g. compound A-101 or salt + bispyribac-sodium or bispyribac-potassium), compound A-lO1 or salt + pyriminobac-methyl or salt, compound A-101 or salt + pyribenzoxim or salt, or compound A-101 or salt + penoxsulam or salt; or compound A-141 or salt + bensulfuron-methyl or salt, compound A-141 or salt + pyrazosulfuron-ethyl or salt, compound A-141 or salt ÷ azimsulfuron or salt, compound A-141 or salt + flucetosulfuron or salt, compound A-141 or salt + orthosulfamuron or salt, compound A-141 or salt + prosulfuron or salt, compound A-141 or salt + triasulfuron or salt, compound A-141 or salt + trifloxysulfuron or salt, compound A-141 or salt + bispyribac or salt (e.g. compound A-141 or salt + bispyribac-sodium or bispyribac-potassium), compound A-141 or -41 -salt + pyriminobac-methyl or salt, compound A-141 or salt + pyribenzoxim or salt, or compound A-141 or salt + penoxsulam or salt; or compound A-142 or salt + bensulfuron-methyl or salt, compound A-142 or salt + pyrazosulfuron-ethyl or salt, compound A-142 or salt + azimsulfuron or salt, compound A-142 or salt + flucetosulfuron or salt, compound A-142 or salt + orthosulfamuron or salt, compound A-142 or salt + prosulfuron or salt, compound A-142 or salt + triasulfuron or salt, compound A-142 or salt + trifloxysulfuron or salt, compound A-142 or salt + bispyribac or salt (e.g. compound A-142 or salt + bispyribac-sodium or bispyribac-potassium), compound A-142 or salt + pyriminobac-methyl or salt, compound A-142 or salt + pyribenzoxim or salt, or compound A-142 or salt + penoxsulam or salt; or compound A-149 or salt + bensulfuron-methyl or salt, compound A-149 or salt + pyrazosulfuron-ethyl or salt, compound A-149 or salt + azimsulfuron or salt, compound A-149 or salt + flucetosulfuron or salt, compound A-149 or salt + orthosulfamuron or salt, compound A-149 or salt + prosulfuron or salt, compound A-149 or salt + triasulfuron or salt, compound A-149 or salt + trifloxysulfuron or salt, compound A-149 or salt + bispyribac or salt (e.g. compound A-149 or salt + bispyribac-sodium or bispyribac-potassium), compound A-149 or salt + pyriminobac-methyl or salt, compound A-149 or salt + pyribenzoxim or salt, or compound A-149 or salt + penoxsulam or salt; or compound A-144 or salt + bensulfuron-methyl or salt, compound A-144 or salt + pyrazosulfuron-ethyl or salt, compound A-144 or salt + azimsulfuron or salt, compound A-144 or salt + flucetosulfuron or salt, compound A-144 or salt + orthosulfamuron or salt, compound A-144 or salt + prosulfuron or salt, compound A-144 or salt + triasulfuron or salt, compound A-144 or salt + trifloxysulfuron or salt, compound A-144 or salt + bispyribac or salt (e.g. compound A-144 or salt + bispyribac-sodium or bispyribac-potassium), compound A-144 or salt + pyriminobac-methyl or salt, compound A-144 or salt + pyribenzoxim or salt, or compound A-144 or salt + penoxsulam or salt; or compound A-154 or salt + bensulfuron-methyl or salt, compound A-154 or salt + pyrazosulfuron-ethyl or salt, compound A-154 or salt + azimsulfuron or salt, compound A-154 or salt + flucetosulfuron or salt, compound A-154 or salt + orthosulfamuron or salt, compound A-154 or salt + prosulfuron or salt, compound A-154 or salt + triasulfuron or salt, compound -42 -A-154 or salt + trifloxysulfuron or salt, compound A-154 or salt + bispyribac or salt (e.g. compound A-154 or salt + bispyribac-sodium or bispyribac-potassium), compound A-154 or salt + pyriminobac-methyl or salt, compound A-154 or salt + pyribenzoxim or salt, or compound A-154 or salt + penoxsulam or salt; or compound A-155 or salt + bensulfuron-methyl or salt, compound A-155 or salt + pyrazosulfuron-ethyl or salt, compound A-155 or salt + azimsulfuron or salt, compound A-155 or salt + flucetosulfuron or salt, compound A-155 or salt + orthosulfamuron or salt, compound A-155 or salt + prosulfuron or salt, compound A-155 or salt + triasulfuron or salt, compound A-155 or salt + trifloxysulfuron or salt, compound A-155 or salt + bispyribac or salt (e.g. compound A-155 or salt + bispyribac-sodium or bispyribac-potassium), compound A-155 or salt + pyriminobac-methyl or salt, compound A-155 or salt ÷ pyribenzoxim or salt, or compound A-155 or salt + penoxsulam or salt; or [particularly preferred]: compound A-158 or salt + bensulfuron-methyl or salt, compound A- 158 or salt + pyrazosulfuron-ethyl or salt, compound A-158 or salt + azimsulfuron or salt, compound A-158 or salt + flucetosulfuron or salt, compound A-158 or salt + orthosulfamuron or salt, compound A-158 or salt + prosulfuron or salt, compound A-158 or salt + triasulfuron or salt, compound A-158 or salt + trifloxysulfuron or salt, compound A-158 or salt + bispyribac or salt (e.g. compound A-158 or salt + bispyribac-sodium or bispyribac-potassium), compound A-158 or salt + pyriminobac-methyl or salt, compound A-158 or salt + pyribenzoxim or salt, or compound A-158 or salt + penoxsulam or salt; or compound 8.007 or salt + bensulfuron-methyl or salt, compound 8.007 or salt + pyrazosulfuron-ethyl or salt, compound 8.007 or salt + azimsulfuron or salt, compound 8.007 or salt + flucetosulfuron or salt, compound 8.007 or salt + orthosulfamuron or salt, compound 8.007 or salt + prosulfuron or salt, compound 8.007 or salt + triasulfuron or salt, compound 8.007 or salt + trifloxysulfuron or salt, compound 8.007 or salt + bispyribac or salt (e.g. compound 8.007 or salt + bispyribac-sodium or bispyribac-potassium), compound 8.007 or salt + pyriminobac-methyl or salt, compound 8.007 or salt + pyribenzoxim or salt, or compound 8.007 or salt + penoxsulam or salt; or compound 8.049 or salt + bensulfuron-methyl or salt, compound 8.049 or salt + pyrazosulfuron-ethyl or salt, compound 8.049 or salt + azimsulfuron or salt, compound 8.049 -43 -or salt + flucetosulfuron or salt, compound 8.049 or salt + orthosulfamuron or salt, compound 8.049 or salt + prosulfuron or salt, compound 8.049 or salt + triasulfuron or salt, compound 8.049 or salt + trifloxysulfuron or salt, compound 8.049 or salt + bispyribac or salt (e.g. compound 8.049 or salt + bispyribac-sodium or bispyribac-potassium), compound 8.049 or salt + pyriminobac-methyl or salt, compound 8.049 or salt + pyribenzoxim or salt, or compound 8.049 or salt + penoxsulam or salt; or compound 8.056 or salt + bensulfuron-methyl or salt, compound 8.056 or salt + pyrazosulfuron-ethyl or salt, compound 8.056 or salt + azimsulfuron or salt, compound 8.056 or salt + flucetosulfuron or salt, compound 8.056 or salt + orthosulfamuron or salt, compound 8.056 or salt + prosulfuron or salt, compound 8.056 or salt + triasulfuron or salt, compound 8.056 or salt + trifloxysulfuron or salt, compound 8.056 or salt ÷ bispyribac or salt (e.g. compound 8.056 or salt + bispyribac-sodium or bispyribac-potassium), compound 8.056 or salt + pyriminobac-methyl or salt, compound 8.056 or salt + pyribenzoxim or salt, or compound 8.056 or salt + penoxsulam or salt; or compound 14.055 or salt + bensulfuron-methyl or salt, compound 14.055 or salt + pyrazosulfuron-ethyl or salt, compound 14.055 or salt + azimsulfuron or salt, compound 14.055 or salt + flucetosulfuron or salt, compound 14.055 or salt + orthosulfamuron or salt, compound 14.055 or salt + prosulfuron or salt, compound 14.055 or salt + triasulfuron or salt, compound 14.055 or salt + trifloxysulfuron or salt, compound 14.055 or salt + bispyribac or salt (e.g. compound 14.055 or salt + bispyribac-sodium or bispyribac-potassium), compound 14.055 or salt + pyriminobac-methyl or salt, compound 14.055 or salt + pyribenzoxim or salt, or compound 14.055 or salt + penoxsulam or salt; or compound 14.056 or salt + bensulfuron-methyl or salt, compound 14.056 or salt + pyrazosulfuron-ethyl or salt, compound 14.056 or salt + azimsulfuron or salt, compound 14.056 or salt + flucetosulfuron or salt, compound 14.056 or salt + orthosulfamuron or salt, compound 14.056 or salt + prosulfuron or salt, compound 14.056 or salt + triasulfuron or salt, compound 14.056 or salt + trifloxysulfuron or salt, compound 14.056 or salt + bispyribac or salt (e.g. compound 14.056 or salt + bispyribac-sodium or bispyribac-potassium), compound 14.056 or salt + pyriminobac-methyl or salt, compound 14.056 or salt + pyribenzoxim or salt, or compound 14.056 or salt + penoxsulam or salt; or -44 -compound 14.058 or salt + bensulfuron-methyl or salt, compound 14.058 or salt + pyrazosulfuron-ethyl or salt, compound 14.058 or salt + azimsulfuron or salt, compound 14.058 or salt + flucetosulfuron or salt, compound 14.058 or salt + orthosulfamuron or salt, compound 14.058 or salt + prosulfuron or salt, compound 14.058 or salt + triasulfuron or salt, compound 14.058 or salt + trifloxysulfuron or salt, compound 14.058 or salt + bispyribac or salt (e.g. compound 14.058 or salt + bispyribac-sodium or bispyribac-potassium), compound 14.058 or salt + pyriminobac-methyl or salt, compound 14.058 or salt + pyribenzoxim or salt, or compound 14.058 or salt + penoxsulam or salt; or [particularly preferred]: compound 14.059 or salt + bensulfuron-methyl or salt, compound 14.059 or salt + pyrazosulfuron-ethyl or salt, compound 14.059 or salt + azimsulfuron or salt, compound 14.059 or salt + flucetosulfuron or salt, compound 14.059 or salt + orthosulfamuron or salt, compound 14.059 or salt + prosulfuron or salt, compound 14.059 or salt + triasulfuron or salt, compound 14.059 or salt + trifloxysulfuron or salt, compound 14.059 or salt + bispyribac or salt (e.g. compound 14.059 or salt + bispyribac-sodium or bispyribac-potassium), compound 14.059 or salt + pyriminobac-methyl or salt, compound 14.059 or salt + pyribenzoxim or salt, or compound 14.059 or salt + penoxsulam or salt; or compound 14.060 or salt + bensulfuron-methyl or salt, compound 14.060 or salt + pyrazosulfuron-ethyl or salt, compound 14.060 or salt + azimsulfuron or salt, compound 14.060 or salt + flucetosulfuron or salt, compound 14.060 or salt + orthosulfamuron or salt, compound 14.060 or salt + prosulfuron or salt, compound 14.060 or salt + triasulfuron or salt, compound 14.060 or salt + trifloxysulfuron or salt, compound 14.060 or salt + bispyribac or salt (e.g. compound 14.060 or salt + bispyribac-sodium or bispyribac-potassium), compound 14.060 or salt + pyriminobac-methyl or salt, compound 14.060 or salt + pyribenzoxim or salt, or compound 14.060 or salt + penoxsulam or salt; or compound 14.073 or salt + bensulfuron-methyl or salt, compound 14.073 or salt + pyrazosulfuron-ethyl or salt, compound 14.073 or salt + azimsulfuron or salt, compound 14.073 or salt + flucetosulfuron or salt, compound 14.073 or salt + orthosulfamuron or salt, compound 14.073 or salt + prosulfuron or salt, compound 14.073 or salt + triasulfuron or salt, compound 14.073 or salt + trifloxysulfuron or salt, compound 14.073 or salt + bispyribac or salt (e.g. compound 14.073 or salt + bispyribac-sodium or bispyribac-potassium), compound -45 - 14.073 or salt + pyriminobac-methyl or salt, compound 14.073 or salt + pyribenzoxim or salt, or compound 14.073 or salt + penoxsulam or salt; or compound 17.035 or salt + bensulfuron-methyl or salt, compound 17.035 or salt + pyrazosulfuron-ethyl or salt, compound 17.035 or salt + azimsulfuron or salt, compound 17.035 or salt + flucetosulfuron or salt, compound 17.035 or salt + orthosulfamuron or salt, compound 17.035 or salt + prosulfuron or salt, compound 17.035 or salt + triasulfuron or salt, compound 17.035 or salt + trifloxysulfuron or salt, compound 17.035 or salt + bispyribac or salt (e.g. compound 17.035 or salt + bispyribac-sodium or bispyribac-potassium), compound 17.035 or salt + pyriminobac-methyl or salt, compound 17.035 or salt + pyribenzoxim or salt, or compound 17.035 or salt + penoxsulam or salt; or compound 17.059 or salt + bensulfuron-methyl or salt, compound 17.059 or salt + pyrazosulfuron-ethyl or salt, compound 17.059 or salt + azimsulfuron or salt, compound 17.059 or salt + flucetosulfuron or salt, compound 17.059 or salt + orthosulfamuron or salt, compound 17.059 or salt + prosulfuron or salt, compound 17.059 or salt + triasulfuron or salt, compound 17.059 or salt + trifloxysulfuron or salt, compound 17.059 or salt + bispyribac or salt (e.g. compound 17.059 or salt + bispyribac-sodium or bispyribac-potassium), compound 17.059 or salt + pyriminobac-methyl or salt, compound 17.059 or salt + pyribenzoxim or salt, or compound 17.059 or salt + penoxsulam or salt; or compound 17.065 or salt + bensulfuron-methyl or salt, compound 17.065 or salt + pyrazosulfuron-ethyl or salt, compound 17.065 or salt + azimsulfuron or salt, compound 17.065 or salt + flucetosulfuron or salt, compound 17.065 or salt + orthosulfamuron or salt, compound 17.065 or salt + prosulfuron or salt, compound 17.065 or salt + triasulfuron or salt, compound 17.065 or salt + trifloxysulfuron or salt, compound 17.065 or salt + bispyribac or salt (e.g. compound 17.065 or salt + bispyribac-sodium or bispyribac-potassium), compound 17.065 or salt + pyriminobac-methyl or salt, compound 17.065 or salt + pyribenzoxim or salt, or compound 17.065 or salt + penoxsulam or salt; or compound 17.066 or salt + bensulfuron-methyl or salt, compound 17.066 or salt + pyrazosulfuron-ethyl or salt, compound 17.066 or salt + azimsulfuron or salt, compound 17.066 or salt + flucetosulfuron or salt, compound 17.066 or salt + orthosulfamuron or salt, compound 17.066 or salt + prosulfuron or salt, compound 17.066 or salt + triasulfuron or salt, -46 -compound 17.066 or salt + trifloxysulfuron or salt, compound 17.066 or salt + bispyribac 01 salt (e.g. compound 17.066 or salt + bispyribac-sodium or bispyribac-potassium), compound 17.066 or salt + pyriminobac-methyl or salt, compound 17.066 or salt + pyribenzoxim or salt, or compound 17.066 or salt + penoxsulam or salt; or compound 17.071 orsalt+ bensulfuron-methyl or salt, compound 17.071 orsalt+ pyrazosulfuron-ethyl or salt, compound 17.071 or salt + azimsulfuron or salt, compound 17.071 or salt + flucetosulfuron or salt, compound 17.071 or salt + orthosulfamuron or salt, compound 17.071 or salt + prosulfuron or salt, compound 17.071 or salt + triasulfuron or salt, compound 17.071 or salt + trifloxysulfuron or salt, compound 17.071 or salt + bispyribac or salt (e.g. compound 17.071 or salt + bispyribac-sodium 01 bispyribac-potassium), compound 17.071 or salt + pyriminobac-methyl or salt, compound 17.071 or salt + pyribenzoxim or salt, or compound 17.071 or salt + penoxsulam or salt; or compound 17.074 or salt + bensulfuron-methyl or salt, compound 17.074 or salt + pyrazosulfuron-ethyl or salt, compound 17.074 or salt + azimsulfuron or salt, compound 17.074 or salt + flucetosulfuron or salt, compound 17.074 or salt + orthosulfamuron or salt, compound 17.074 or salt + prosulfuron or salt, compound 17.074 or salt + triasulfuron or salt, compound 17.074 or salt + trifloxysulfuron or salt, compound 17.074 or salt + bispyribac or salt (e.g. compound 17.074 or salt + bispyribac-sodium 01 bispyribac-potassium), compound 17.074 or salt + pyriminobac-methyl or salt, compound 17.074 or salt + pyribenzoxim or salt, or compound 17.074 or salt + penoxsulam or salt; or compound 17.084 or salt + bensulfuron-methyl or salt, compound 17.084 or salt + pyrazosulfuron-ethyl or salt, compound 17.084 or salt + azimsulfuron or salt, compound 17.084 or salt + flucetosulfuron or salt, compound 17.084 or salt + orthosulfamuron or salt, compound 17.084 or salt + prosulfuron or salt, compound 17.084 or salt + triasulfuron or salt, compound 17.084 or salt + trifloxysulfuron or salt, compound 17.084 or salt + bispyribac or salt (e.g. compound 17.084 or salt + bispyribac-sodium or bispyribac-potassium), compound 17.084 or salt + pyriminobac-methyl or salt, compound 17.084 or salt + pyribenzoxim or salt, or compound 17.084 or salt + penoxsulam or salt; or compound 18.049 or salt + bensulfuron-methyl or salt, compound 18.049 or salt + pyrazosulfuron-ethyl or salt, compound 18.049 or salt + azimsulfuron or salt, compound -47 - 18.049 or salt + flucetosulfuron or salt, compound 18.049 or salt + orthosulfamuron or salt, compound 18.049 or salt + prosulfuron or salt, compound 18.049 or salt + triasulfuron or salt, compound 18.049 or salt + trifloxysulfuron or salt, compound 18.049 or salt+ bispyribac or salt (e.g. compound 18.049 or salt + bispyribac-sodium or bispyribac-potassium), compound 18.049 or salt + pyriminobac-methyl or salt, compound 18.049 or salt + pyribenzoxim or salt, or compound 18.049 or salt + penoxsulam or salt; or compound 18.058 or salt + bensulfuron-methyl or salt, compound 18.058 or salt + pyrazosulfuron-ethyl or salt, compound 18.058 or salt + azimsulfuron or salt, compound 18.058 or salt + flucetosulfuron or salt, compound 18.058 or salt + orthosulfamuron or salt, compound 18.058 or salt + prosulfuron or salt, compound 18.058 or salt + triasulfuron or salt, compound 18.058 or salt + trifloxysulfuron or salt, compound 18.058 or salt + bispyribac or salt (e.g. compound 18.058 or salt + bispyribac-sodium or bispyribac-potassium), compound 18.058 or salt + pyriminobac-methyl or salt, compound 18.058 or salt + pyribenzoxim or salt, or compound 18.058 or salt + penoxsulam or salt; or compound 18.060 or salt + bensulfuron-methyl or salt, compound 18.060 or salt + pyrazosulfuron-ethyl or salt, compound 18.060 or salt + azimsulfuron or salt, compound 18.060 or salt + flucetosulfuron or salt, compound 18.060 or salt + orthosulfamuron or salt, compound 18.060 or salt + prosulfuron or salt, compound 18.060 or salt + triasulfuron or salt, compound 18.060 or salt + trifloxysulfuron or salt, compound 18.060 or salt + bispyribac or salt (e.g. compound 18.060 or salt + bispyribac-sodium or bispyribac-potassium), compound 18.060 or salt + pyriminobac-methyl or salt, compound 18.060 or salt + pyribenzoxim or salt, or compound 18.060 or salt + penoxsulam or salt; or [particularly preferred]: compound 20.049 or salt + bensulfuron-methyl or salt, compound 20.049 or salt + pyrazosulfuron-ethyl or salt, compound 20.049 or salt + azimsulfuron or salt, compound 20.049 or salt + flucetosulfuron or salt, compound 20.049 or salt + orthosulfamuron or salt, compound 20.049 or salt + prosulfuron or salt, compound 20.049 or salt + triasulfuron or salt, compound 20.049 or salt + trifloxysulfuron or salt, compound 20.049 or salt + bispyribac or salt (e.g. compound 20.049 or salt + bispyribac-sodium or bispyribac-potassium), compound 20.049 or salt + pyriminobac-methyl or salt, compound 20.049 or salt + pyribenzoxim or salt, or compound 20.049 or salt + penoxsulam or salt; or -48 -compound 20.052 or salt + bensulfuron-methyl or salt, compound 20.052 or salt + pyrazosulfuron-ethyl or salt, compound 20.052 or salt + azimsulfuron or salt, compound 20.052 or salt + flucetosulfuron or salt, compound 20.052 or salt + orthosulfamuron or salt, compound 20.052 or salt + prosulfuron or salt, compound 20.052 or salt + triasulfuron or salt, compound 20.052 or salt + trifloxysulfuron or salt, compound 20.052 or salt + bispyribac or salt (e.g. compound 20.052 or salt + bispyribac-sodium or bispyribac-potassium), compound 20.052 or salt + pyriminobac-methyl or salt, compound 20.052 or salt + pyribenzoxim or salt, or compound 20.052 or salt + penoxsulam or salt; or compound 20.055 or salt + bensulfuron-methyl or salt, compound 20.055 or salt + pyrazosulfuron-ethyl or salt, compound 20.055 or salt + azimsulfuron or salt, compound 20.055 or salt + flucetosulfuron or salt, compound 20.055 or salt + orthosulfamuron or salt, compound 20.055 or salt + prosulfuron or salt, compound 20.055 or salt + triasulfuron or salt, compound 20.055 or salt + trifloxysulfuron or salt, compound 20.055 or salt + bispyribac or salt (e.g. compound 20.055 or salt + bispyribac-sodium or bispyribac-potassium), compound 20.055 or salt + pyriminobac-methyl or salt, compound 20.055 or salt + pyribenzoxim or salt, or compound 20.055 or salt + penoxsulam or salt; or [particularly preferred]: compound 20.056 or salt + bensulfuron-methyl or salt, compound 20.056 or salt + pyrazosulfuron-ethyl or salt, compound 20.056 or salt + azimsulfuron or salt, compound 20.056 or salt + flucetosulfuron or salt, compound 20.056 or salt + orthosulfamuron or salt, compound 20.056 or salt + prosulfuron or salt, compound 20.056 or salt + triasulfuron or salt, compound 20.056 or salt + trifloxysulfuron or salt, compound 20.056 or salt + bispyribac or salt (e.g. compound 20.056 or salt + bispyribac-sodium or bispyribac-potassium), compound 20.056 or salt + pyriminobac-methyl or salt, compound 20.056 or salt + pyribenzoxim or salt, or compound 20.056 or salt + penoxsulam or salt; or compound 20.058 or salt + bensulfuron-methyl or salt, compound 20.058 or salt + pyrazosulfuron-ethyl or salt, compound 20.058 or salt + azimsulfuron or salt, compound 20.058 or salt + flucetosulfuron or salt, compound 20.058 or salt + orthosulfamuron or salt, compound 20.058 or salt + prosulfuron or salt, compound 20.058 or salt + triasulfuron or salt, compound 20.058 or salt + trifloxysulfuron or salt, compound 20.058 or salt + bispyribac or salt (e.g. compound 20.058 or salt + bispyribac-sodium or bispyribac-potassium), compound -49 - 20.058 or salt + pyriminobac-methyl or salt, compound 20.058 or salt + pyribenzoxim or salt, or compound 20.058 or salt + penoxsulam or salt; or compound 20.059 or salt + bensulfuron-methyl or salt, compound 20.059 or salt + pyrazosulfuron-ethyl or salt, compound 20.059 or salt + azimsulfuron or salt, compound 20.059 or salt + flucetosulfuron or salt, compound 20.059 or salt + orthosulfamuron or salt, compound 20.059 or salt + prosulfuron or salt, compound 20.059 or salt + triasulfuron or salt, compound 20.059 or salt + trifloxysulfuron or salt, compound 20.059 or salt + bispyribac or salt (e.g. compound 20.059 or salt + bispyribac-sodium or bispyribac-potassium), compound 20.059 or salt + pyriminobac-methyl or salt, compound 20.059 or salt + pyribenzoxim or salt, or compound 20.059 or salt + penoxsulam or salt; or compound 20.060 or salt + bensulfuron-methyl or salt, compound 20.060 or salt + pyrazosulfuron-ethyl or salt, compound 20.060 or salt + azimsulfuron or salt, compound 20.060 or salt + flucetosulfuron or salt, compound 20.060 or salt + orthosulfamuron or salt, compound 20.060 or salt + prosulfuron or salt, compound 20.060 or salt + triasulfuron or salt, compound 20.060 or salt + trifloxysulfuron or salt, compound 20.060 or salt + bispyribac or salt (e.g. compound 20.060 or salt + bispyribac-sodium or bispyribac-potassium), compound 20.060 or salt + pyriminobac-methyl or salt, compound 20.060 or salt + pyribenzoxim or salt, or compound 20.060 or salt + penoxsulam or salt.

Formulations and formulation ingredients The herbicidal compositions of the present invention can be prepared in a variety of ways using various formulation aids, such as carriers (e.g. liquid or solid carrier), solvents and/or surface-active substances. Therefore, preferably, the herbicidal composition of the present invention is a formulation comprising a carrier (e.g. liquid or solid carrier, preferably liquid), a solvent and/or a surface-active substance.

The herbicidal composition can be in various physical forms, for example in the form of a dustable powder (DP), a gel, a wettable powder (WP), a granule (GR) (such as an emulsifiable granule (EG) or more particularly a water-dispersible granule (WG)), a water-dispersible tablet (WT), an effervescent compressed tablet, an emulsifiable concentrate (EC), a microemulsifiable concentrate, an oil-in-water emulsion (E\A, an oil flowable (e.g. a -50 -spreading oil (SO)), an aqueous dispersion (e.g. aqueous suspension concentrate (SC)), an oily dispersion (CD), a suspo-emulsion (SE), a capsule suspension (CS), a soluble liquid, a water-soluble concentrate (with water or a water-miscible organic solvent as carrier), an impregnated polymer film, or in another form such as a form known, for example, from the Manual on Development and Use of FAQ Specifications for Plant Protection Products, 5th Edition, 1999.

Preferably, the herbicidal composition is in the form of a wettable powder!P), a granule (GR) (such as an emulsifiable granule (EG) or more particularly a water-dispersible granule (WG)), an emulsifiable concentrate (EC), a microemulsifiable concentrate, an oil-in-water emulsion (EW), an oil flowable (e.g. a spreading oil (SO)), an aqueous dispersion (e.g. aqueous suspension concentrate (SC)), an oily dispersion (CD), a soluble liquid, or a water-soluble concentrate (wherein the water-soluble concentrate is with water or a water-miscible organic solvent as carrier).

More preferably, the herbicidal composition is in the form of an emulsifiable concentrate (EC).

The herbicidal composition of the invention can for example be used directly or, more typically, can be diluted prior to use. Diluted liquid herbicidal compositions can be prepared, for example, by mixing (e.g. in a tank) the herbicidal composition of the invention with water, fertiliser(s) (e.g. liquid or granular fertiliser(s)), micronutrient(s), biological organism(s), oil and/or solvent(s); and/or by mixing the herbicidal composition of the invention with water and optionally other ingredients (typically fertiliser(s), micronutrient(s), biological organism(s), oil and/or solvent(s)).

The herbicidal compositions can be prepared. for example, by mixing the active ingredient with one or more formulation aids. The composition can e.g. be formed in the form of finely divided solids, granules, solutions, dispersions or emulsions. The active ingredients can also be mixed with other formulation aids, for example finely divided solids, mineral oils, vegetable oils, modified vegetable oils, organic solvents, water, surface-active substances or combinations thereof. The active ingredients can also be contained in very fine microcapsules consisting of a polymer. Microcapsules contain the active ingredients in a porous carrier. This enables the active ingredients to be released into their surroundings in controlled amounts (e.g. slow release). Microcapsules usually have a diameter of from 0.1 to 500 microns. They contain active ingredients in an amount of about from 25 to 95 % by -51 -weight of the capsule weight. The active ingredients can be present in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution. The encapsulating membranes comprise, for example, natural and synthetic gums, cellulose, styrene-butadiene copolymers, polyacrylonitrile, polyacrylate, polyester, polyamides, polyureas, polyurethane or chemically modified polymers and starch xanthates or other polymers that are known to the person skilled in the art in this connection.

Alternatively it is possible for very fine microcapsules to be formed wherein the active ingred-ient is present in the form of finely divided particles in a solid matrix of a base substance, but in that case the microcapsule is not encapsulated.

The formulation aids suitable for the preparation of the compositions according to the invention can include those known perse.

As liquid carrier (and/or solvent) there may be used: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylenes carbonate, chlorobenzene, cyclo-hexane, cyclohexanol, alkyl esters of acetic acid (e.g. ethyl acetate, butyl acetate, amyl acetate, or isoamyl acetate, et al), diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylfomiamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone, ethyl acetate, 2-ethyl-hexanol, ethylene carbonate, 1,1,1 -trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG 400), propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, or higher molecular weight alcohols (i.e. an alcohol having a higher molecular weight than isopropanol, such as amyl alcohol, tetrahydrofurfuryl alcohol, -52 -hexanol, octanol, 2-ethyl-hexanol, cyclohexanol, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, hexylene glycol, or glycerol), or N-methyl-2-pyrrolidone, N-octyl-2-pyrrolidone, a mixture of heavy aromatic hydrocarbons (e.g. containing a mixture of C1-C4alkylnaphthalenes and optionally also naphthalene, e.g. Solvesso 200 TM) or a similar liquid carrier (and/or a similar solvent).

Water is generally the carrier of choice for the dilution of a concentrate (e.g. emulsifiable concentrate) herbicidal composition.

Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica (silicon dioxide), attapulgite clay, kieselguhr, limestone, calcium carbonate, bentonite, calcium montomorillonite, cottonseed husks, wheatmeal, soybean flour, pumice, wood flour, ground walnut shells, lignin and/or similar materials, as described, for example, in CFR 180.1001. (c) &(d).

A surface-active substance can advantageously be used both in solid and in liquid herbicidal compositions, especially in those herbicidal compositions which can be diluted with a carrier prior to use. Surface-active substances may be anionic, cationic, non-ionic or polymeric and they may be used as emulsifiying, wetting or suspending agents or for other purposes.

Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of alkylarylsulfonates, such as calcium dodecyl-benzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride, polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono-and di-alkyl phosphate esters; and also further substances described e.g. in "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, 1981.

Further formulation aids which can usually be used in the herbicidal composition include crystallisation inhibitors, viscosity-modifying substances, suspending agents, dyes, anti-oxidants, foaming agents, light absorbers, mixing aids, anti-foams, complexing agents, neutralising or pH-modifying substances and/or buffers, corrosion-inhibitors, fragrances, -53 -wetting agents, absorption improvers, micronutrients, plasticisers, glidants, lubricants, dispersants, thickeners, anti-freezes, microbiocides, and/or liquid and/or solid fertilisers.

The herbicidal compositions may also comprise additional active substances, for example one or more further herbicides, herbicide safeners, plant growth regulators, fungicides and/or insecticides.

The compositions according to the invention can additionally include an additive comprising an oil of vegetable or animal origin, a mineral oil, alkyl esters of such oils or mixtures of such oils and oil derivatives. The amount of oil additive used in the composition according to the invention is generally from 0.01 to 10 %, based on the spray mixture. For example, the oil additive can be added to the spray tank in the desired concentration after the spray mixture has been prepared. Preferred oil additives comprise mineral oils or an oil of vegetable origin, for example rapeseed oil, olive oil or sunflower oil, emulsified vegetable oil, such as AMIGO® (Rhône-Foulenc Canada Inc.), alkyl esters of oils of vegetable origin, for example the methyl derivatives, or an oil of animal origin, such as fish oil or beef tallow. A preferred additive contains, for example, as active components essentially 80 % by weight alkyl esters of fish oils and 15 % by weight methylated rapeseed oil, and also 5 % by weight of customary emulsifiers and pH modifiers. Especially preferred oil additives comprise alkyl esters of CrC22 fatty acids, especially the methyl derivatives of C12-C13 fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid, being important. Those esters are known as methyl laurate (CAS-111-82-0), methyl palmitate(CAS-112-39-0) and methyl oleate (CAS-1 12-62-9). A preferred fatty acid methyl ester derivative is Emery® 2230 and 2231 (Cognis GmbH). Those and other oil derivatives are also known from the Compendium of Herbicide Adjuvants, 5th Edition, Southern Illinois University, 2000.

The application and action of the oil additives can be further improved by combining them with surface-active substances, such as non-ionic, anionic or cationic surfactants. Examples of suitable anionic, non-ionic and cationic surfactants are listed on pages 7 and 8 of WO 97/34485. Preferred surface-active substances are anionic surfactants of the dodecyl-benzylsulfonate type, especially the calcium salts thereof, and also non-ionic surfactants of the fatty alcohol ethoxylate type. Special preference is given to ethoxylated C12-C22 fatty alcohols having a degree of ethoxylation of from 5 to 40. Examples of commercially available surfactants are the Genapol types (Clariant AG). Also preferred are silicone surfactants, especially polyalkyl-oxide-modified heptamethyltrisiloxanes, which are commercially available e.g. as Silwet L-77®, and also perfluorinated surfactants. The concentration of -54 -surface-active substances in relation to the total additive is generally from 1 to 30 % by weight. Examples of oil additives that comprise or consist of mixtures of oils or mineral oils or derivatives thereof with surfactants are Edenor ME SU®, Turbocharge® (a mixture of surfactant, 1-octanol and petroleum oil) (Syngenta AG, OH), and Actipron® (BP Oil UK Limited, GB).

The said surface-active substances may also be used in the herbicidal compositions alone, that is to say without oil additives.

Furthermore, the addition of an organic solvent to the oil additive/surfactant mixture can contribute to a further enhancement of action. Suitable solvents are, for example, Solvesso® (ESSO) and Alomatic Solvent® (Exxon Corporation).The concentration of such solvents can be from 10 to 80 % by weight of the total weight. Such oil additives, which may be in admixture with solvents, are described, for example, in US-A-4 834 908. A commercially available oil additive disclosed therein is known by the name MERGE® (BASF Corporation).

A further oil additive that is preferred according to the invention is SCORE® (Syngenta Crop Protection Canada.) In addition to the oil additives listed above, in order to enhance the activity of the composi-tions according to the invention it is also possible for compositions of alkylpyrrolidones, (e.g. Agrimax®) to be added to the spray mixture. Compositions of synthetic latices, such as, for example, polyacrylamide, polyvinyl compounds or poly-1-p-menthene (e.g. Bond®, Courier® or Emerald®) can also be used. Solutions that contain propionic acid, for example Eurogkem Pen-e-trate®, can also be mixed into the spray mixture as activity-enhancing agents.

The herbicidal compositions generally contain: (a) from 0.1 to 99 % by weight, especially from 0.5 to 95 % by weight, more especially from 1 to 60 % by weight or from ito 40 % by weight, of the compound of formula (I) or the salt thereof; and (b) from 0.1 to 99 % by weight, especially from 0.5 to 95 % by weight, more especially from i to 60 % by weight or from ito 40 % by weight, of the rice-suitable ALS inhibitor herbicide; and (b) from 5 to 99.5%, or from 20 to 98%, or from 40% to 95%, by weight) of one or more formulation aids (e.g. a total of from 5 to 99.5%, or from 20 to 98%, or from 40% to 95%, by weight of the herbicidal composition, of: any carrier (e.g. liquid or solid carrier) (if present), -55 -any solvent (if present), any surface-active substance (if present), and any other formulation aids which may be present).

The formulation aid(s) preferably include(s) from ito 25 % by weight of a surface-active substance, e.g. one or more emulsifiers.

Unless the context requires otherwise, in this specification, % by weight means % by weight of the herbicidal composition.

i0 Wiereas commercial products (e.g. liquid herbicidal compositions) will preferably be formulated as concentrates, the end user will normally employ diluted formulations.

Preferred formulations have especially the following compositions: = percent by weight of the herbicidal composition or formulation): i5 Emulsifiable concentrates: active ingredient: ito 95 %, in particular ito 60 % (e.g. ito 40 %) or 60 to % surface-active agent: ito 30 %, preferably 5 to 30 % or 5 to 20 % liquid carrier (and/or solvent): ito 90 % or ito 80 %, in particular ito 35 % or 35 to 90 % (such as 35 to 80 %) Dusts: active ingredient: 0.i to iO %, preferably 0.i to 5 % solid carrier: 99.9 to 90 %, preferably 99.9 to 99 % Suspension concentrates: active ingredient: 2 to 75 % or 5 to 75 %, preferably iO to 50 % water: 94 to 24 %, preferably 88 to 30 % surface-active agent: ito 40 %, preferably 2 to 30 %

Wettable powders:

active ingredient: 0.5 to 90 %, preferably i to 80 % surface-active agent: 0.5 to 20 %, preferably ito iS % solid carrier: 5 to 95 %, preferably 15 to 90 % -56 -Granules: active ingredient: 0.1 to 30 %, preferably 0.1 to 15 % solid carrier: 99.5 to 70 010 preferably 97 to 85 %, where the term "active ingredient" refers to the mixture of compound of formula (I) with a co-herbicide.

The following Examples further illustrate, but do not limit, the invention.

El. Emulsifiable concentrates a) b) c) d) active ingredient 5 % 10% 25% 50% calcium dodecylbenzene-sulfonate 6% 8% 6% 8% castor oil polyglycol ether 4 % -4 % 4 % (36 mol of ethylene oxide) octylphenol polyglycol ether -4 % -2 % (7-8 mol of ethylene oxide) NMP (N-methylpyrrolidone) --10% 20% aromatic hydrocarbon 85 % 78 % 55 % 16 % mixture C9-C12 Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.

E2. Solutions a) b) c) d) active ingredient 5 % 10 % 50 % 90 % 1 -methoxy-3-(3-methoxy- propoxy)-propane -20 % 20 % - polyethylene glycol MW 400 20% 10% --NMP (N-methylpyrrolidone) --30% 10 % aromatic hydrocarbon 75 % 60 % --mixture C9-C12 The solutions are suitable for application in the form of microdrops.

F3. Wettable powders a) b) c) d) active ingredient 5 % 25 % 50% 80 % -57 -sodium lignosulfonate 4 % -3 % sodium lauryl sulfate 2 % 3 % -4 % sodium diisobutylnaphthalene-sulfonate -6% 5% 6% octylphenol polyglycol ether -1 % 2 % (7-8 mol of ethylene oxide) highly dispersed silicic acid 1 % 3 % 5 % 10% kaolin 88% 62% 35% The active ingredient is thoroughly mixed with the formulation aid(s) and the mixture is thoroughly ground in a suitable mill, yielding wettable powders which can be diluted with water to give suspensions of any desired concentration.

F4. Coated granules a) b) c) active ingredient 0.1 % 5 % 15 % highly dispersed silicic acid 0.9 % 2 % 2 % inorganic carrier 99.0 % 93 % 83 % (diameter 0.1 -1 mm) e.g. CaCO3 or Si02 The active ingredient is dissolved in methylene chloride, the solution is sprayed onto the carrier and the solvent is subsequently evaporated off/n vacuo.

F5. Coated aranules a) b) c) active ingredient 0.1 % S % 15 % polyethylene glycol MW 200 1.0 % 2 % 3 % highly dispersed silicic acid 0.9 % 1 % 2 % inorganic carrier 98.0 % 92 % 80 % (diameter 0.1 -1 mm) e.g. CaCO3 or Si02 The finely ground active ingredient is applied uniformly, in a mixer, to the carrier moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.

ES. Extruder granules a) b) c) d) active ingredient 0.1 % 3 % 5 % 15 % sodium lignosulfonate 1.5% 2% 3% 4% carboxymethylcellulose 1.4% 2% 2 % 2% kaolin 97.0% 93% 90% 79% -58 -The active ingredient is mixed and ground with the formulation aid(s) and the mixture is moistened with water. The resulting mixture is extruded and then dried in a stream of air.

F7. Dusts a) b) c) active ingredient 0.1 % 1 % 5 % talcum 39.9 % 49 % 35 % kaolin 60.0 % 50% 60 % Ready-to-use dusts are obtained by mixing the active ingredient with the carriers and grinding the mixture in a suitable mill.

F8. Suspension concentrates a) b) c) d) active ingredient 3 % 10% 25% 50 % ethyleneglycol 5% 5% 5% 5% nonylphenol polyglycol ether -1 % 2 % - (15 mol of ethylene oxide) sodium lignosulfonate 3 % 3 % 4 % 5 % carboxymethylcellulose 1 % 1 % 1 % 1 % 37 % aqueous formaldehyde 0.2 % 0.2 % 0.2 % 0.2 % solution silicone oil emulsion 0.8 % 0.8 % 0.8 % 0.8 % water 87% 79% 62% 38% The finely ground active ingredient is intimately mixed with the formulation aid(s), yielding a suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water.

The term active ingredient" in the examples mentioned above refers to the mixture of compound of formula (I) with a co-herbicide.

Herbicidal uses A second aspect of the present invention relates to a method of controlling weeds in crops of useful plants, which comprises applying a herbicidal composition of the invention as defined herein to the weeds and/or useful plants (preferably flooded weeds and/or flooded useful plants) and/or to the locus (preferably the flooded locus) thereof. More preferably, the -59 -method comprises applying the herbicidal composition to the flood-waters at the flooded locus of the flooded weeds and/or flooded useful plants.

The second aspect of the invention also relates also to a method for the control (e.g. selective control) of weeds in crops of useful plants, which comprises treating the weeds and/or useful plants (preferably flooded weeds and/or flooded useful plants), and/or the area under cultivation (preferably the flooded area), and/or the locus (preferably the flooded locus) thereof, with a herbicidal composition according to this invention. More preferably, the method comprises applying the herbicidal composition to the flood-waters at the flooded locus of the flooded weeds and/or flooded useful plants.

The invention also relates to a herbicidal composition as defined herein, for controlling weeds in crops of useful plants (e.g. flooded plants), especially in crops of rice (e.g. flooded rice).

In all aspects of the invention, the application of the herbicidal composition is preferably post-emergence (e.g. after the emergence of the crop(s) and/or the weed(s)).

The crops of useful plants, e.g. in which the compositions according to the invention can be used, are in particular cereals, cotton, soybeans, sugar beet, sugar cane, potatoes, plantation crops, rape (e.g. oilseed rape), maize or rice; or more particularly cotton, soybeans, sugar beet, sugar cane, potatoes, rape (e.g. oilseed rape), or rice.

The crops of useful plants are preferably rice, in particular indica rice (such as IR-64, Ciherang, Pusa e.g. Pusa-1121, Jiayu 293, 01 NK-3325 hybrid); orjaponica rice (such as Koshihikari, Arborio, or Liangyou peiju e.g. Liangyou peiju PS3100).

The rice is preferably flooded rice.

The rice can for example be direct-seeded [e.g. dry-sown (dry-seeded) or wet-sown] rice; which can optionally be flooded (e.g. before or after the herbicidal composition is applied).

However, preferably the rice is transplanted rice, which is typically flooded (e.g. before the herbicidal composition is applied).

The weeds to be controlled may be monocotyledonous and/or dicotyledonous weeds, such as, for example, Echinochloa (e.g. Echinoch/oa crus-ga/li), Brachiaria (e.g. Bra chiaria plantaginia), Leptochloa (e.g. Leptochioa chinensis), Digitaria, Setaria, Scirpus (e.g. Scirpus -60 -marit/mus or Scirpus juncoides), Monochoria, Fimbristylis, Cyperus, Commelina, Sagittaria, Elatine, Lindernia, Ludwigia, Stellaria, Nasturtium, Agrostis, Avena, Sinapis, Lolium, Solanum, Bromus, Alopecurus, Sorghum, Rottboellia, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, I pomoea, Chrysanthemum, Galium, Viola, Veronica, and/or Schoenoplectus.

Preferably, the weeds to be controlled comprise: monocotyledonous weeds, and/or weeds found in rice fields e.g. rice paddy fields. Preferably, the weeds to be controlled comprise: Echinochloa (e.g. Echinochloa crus-galli (ECHCG), Echinochloa otyzoides, Echinoch/oa co/ona or co/onum (ECHCO), Ech/noch/oa crus-pavonis, or Echinoch/oa oryzicola; or Echinoch/oa muricata or Echinoch/oa stagnina), Brachiaria (e.g. Brachiaria p/antagin/a (BRAPL)), Leptochloa (e.g. Leptochloa chinensis (LEECH) or Leptochloa pan/co/des), Digitaria, Setaria, Scirpus (e.g. Scirpus maritimus (SCPMA), Scirpusjuncoides (SCPJU), Scirpus marit/mus, Scirpus fluviatilis, Scirpus pendulus, Scirpus triangulatus, or one of many other Scirpus species), Monochoria (e.g. Monochoria vagina/is (MOOVA) or Monochoria korsakovil), Fimbristylis (e.g. F/mix/sty//s m//iacea (FIMMD), Cyperus (e.g. Cyperus serot/nus), Commelina, Sagittaria, Elatine, Lindernia and/or Ludwigia; and/or Schoenoplectus (e.g. Schoenop/ectus mucronatus or Schoenop/ectusjuncoides).

More preferably, the weeds to be controlled comprise: Echinochloa (e.g. Echinoch/oa crus-ga/li (ECHCG), Fch/noch/oa oryzo/des, Echinoch/oa co/ona or co/onum (ECHCO), Echinoch/oa crus-pa von/s7 or Echinoch/oa oryzico/a; or Echinoch/oa muricata or Ech/noch/oa stagnina), Brachiaria (e.g. Brachiaria p/anta gin/a (BRAPL)), Leptochloa (e.g. Leptochioa chinensis (LEFCH) or Leptoch/oa pan/co/des), Scirpus (e.g. Scirpus maritimus (SCPMA), Scirpus juncoides (SCPJ U), Scirpus maritimus, Sc/rpus fluviatilis, Scirpus pendulus, Sc/rpus triangu/atus, or one of many other Scirpus species), Monochoria (e.g. Monochoria vagina/is (MOOVA) or Monochoria korsakovii), Fimbristylis (e.g. Fimbristy/is mi//acea (FIMMfl), and/or Cyperus (e.g. Cyperus serot/nus).

Most preferably, the weeds to be controlled comprise Echinochloa, such as Echinoch/oa crus-ga/// (ECHCG), and/or Brachiaria, such as Brachiaria p/anta gin/a (BRAPL).

Still more preferably, the weeds to be controlled (e.g. comprising Echinochloa) are in crops of flooded rice, especially crops of flooded transplanted rice. -61 -

The term "crops" is to be understood as also including crops that have been rendered tolerant to herbicides or classes of herbicides (for example ALS, GS, EPSPS, PPO, ACCase or HPPD inhibitors) as a result of conventional methods of breeding or genetic engineering.

Examples of crop that have been rendered tolerant e.g. to imidazolinones, such as imazamox, by conventional methods of breeding are Clearfield® summer rape (Canola) or Clearfield® rice. Examples of crops that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate-resistant or glufosinate-resistant maize or rice varieties, e.g. those commercially available under the trade names RoundupReady® (glyphosate-resistant maize or rice) or LibertyLink® (glufosinate-resistant maize or rice).

Crops are also to be understood as being those which have been rendered resistant to harmful insects by genetic engineering methods, for example Bt maize (resistant to European corn borer), St cotton (resistant to cotton boll weevil) and also St potatoes (resistant to Colorado beetle). Examples of St maize are the Bt-176 maize hybrids of NK® (Syngenta Seeds). The Bttoxin is a protein that is formed naturally by Bacillus thuringiensis soil bacteria. Examples of toxins and transgenic plants able to synthesise such toxins are described in EP-A-451 878, EP-A-374 753, WO 93/07278, WO 95/34656, WO 03/052073 and EP-A-427 529. Examples of transgenic plants that contain one or more genes which code for an insecticidal resistance and express one or more toxins are Knockaut® (maize), Yield Gard® (maize), NuCaTIN33B® (cotton), Sollgard® (cotton), NewLeaf® (potatoes), NatureGard® and Protexcta®. Plant crops and their seed material can be resistant to herbicides and at the same time also to insect feeding ("stacked" transgenic events). Seed can, for example, have the ability to express an insecticidally active Cry3 protein and at the same time be glyphosate-tolerant. The term "crops" is to be understood as also including crops obtained as a result of conventional methods of breeding or genetic engineering which contain so-called output traits (e.g. improved flavour, storage stability, nutritional content).

Areas under cultivation are to be understood as including land where the crop plants are already growing as well as land intended for the cultivation of those crop plants.

The rates of application of each of the herbicides (the compound of formula (I) or salt, and separately the rice-suitable ALS inhibitor herbicide) may vary within wide limits, and for example can depend upon the nature of the soil, the method of application (pre-or post-emergence; seed dressing; application to the seed furrow; no tillage application etc.), the crop plant, the weed to be controlled, the prevailing climatic conditions, and/or other factors governed by the method of application, the time of application and/or the target crop.

-62 -In the method of controlling (or for the control of) weeds in crops of useful plants (e.g. rice) and/or in the herbicidal composition for controlling weeds in crops of useful plants (e.g. rice), according to the invention, and/or in other aspects of the invention, preferably, the herbicidal composition is applied to the plants and/or the weeds, or to the locus thereof, at an application rate as defined below.

Preferably, in general, the application rate for the compound of formula (I) or the salt thereof (e.g. Compound no. 1 or 2, or a salt thereof), is: from 30 to 250 g/ha, e.g. 60, 90, 120 or 240 g/ha; preferably from 50 to 180 g/ha or from 50 to 150 g/ha, e.g. 60, 90 or 120 g/ha; more preferably from 80 to 130 g/ha or from 90 to 120 g/ha, e.g. 90 01120 g/ha; of the compound of formula (I) or a salt thereof (e.g. Compound no. 1 or 2, or a salt thereof), calculated as the free compound. "ha" = hectare.

Preferably, in general, the preferred application rates (especially for post-emergence application) for the rice-suitable ALS inhibitor herbicide are as follows, all calculated as the free compound (in respect of the stated rice-suitable ALS inhibitor herbicide): Bi. bensulfuron-methyl Application rates (preferably for post-emergence application): Broadest ranges: from 20 to 120 g/ha.

Preferable range: from 30 to 90 g/ha.

More preferable range: from 40 to 70 g/ha.

Most preferable range: from 45 to 65 glha -eg 50 or 60 g/ha.

B2. pyrazosulfuron-ethyl Application rates (preferably for post-emergence application): Broadest ranges: from 7 to 60 g/ha.

Preferable range: from 10 to 50 g/ha.

More preferable range: from 10 to 40 g/ha.

Most (or even more) preferable range: from 15 to 30 g/ha -eg 20 or 21 g/ha.

B3. azimsulfuron -7-50, preferably 10-40, more preferably 15-30, most preferably 20-25 g/ha.

-63 -B4. flucetosulfuron -7-60, preferably 10-50, more preferably 15-40, most preferably 20-30 g/ha B5. orthosulfamuron -15-150, preferably 20-100, more preferably 25-75. most preferably 40-75 glha B6. prosulfuron -4-60, preferably 5-50, more preferably 7-40, most preferably 12-30 g/ha B7. triasulfuron -1.5-20, preferably 2-15, more preferably 3-10, most preferably 5-10 g/ha B8. trifloxysulfuron -1.5-100, preferably 2-80, more preferably 3-70, most preferably 5-65 g/ha B9. bispyribac Application rates (preferably for post-emergence application): Broadest ranges: from 10 to 70 g/ha.

Preferable range: from 15 to 50 g/ha.

More preferable range: from 20 to 40 g/ha -eg 20, 25, 30 g/ha.

Most preferable range: from 25 to 35 g/ha -eg 25, 30 g/ha.

BlO. pyriminobac-methyl -12-175, preferably 15-150, more preferably 20-140, most preferably 30-120 g/ha Bli. pyribenzoxim -10-70, preferably 15-50, more preferably 20-40, most preferably 30 g/ha B12. penoxsulam Application rates (preferably for post-emergence application): Broadest ranges: from 2 to 60 g/ha.

Preferable range: from 4 to 50 g/ha -eg 5, 10, 12, 15, 20, 25, or 30 g/ha..

More preferable range: from 10 to 40 g/ha -eg 10, 12, 15, 20, 25, or 30 g/ha.

Most (or even more) preferable range: from 15 to 30 g/ha -eg 15, 20, 25, or 30 g/ha.

-64 -Preferably, for application (preferably foliar and/or spray application) to direct-seeded rice (e.g. dry-seeded rice or wet-sown rice; and/or preferably direct-seeded flooded rice), the application rate for the compound of formula (I) or the salt thereof (e.g. Compound no. 1 or 2, or a salt thereof), is: from 30 to 250 g/ha, preferably from 30 to 180 g/ha or from 30 to 150 g/ha, more preferably from 30 to 130 g/ha, still more preferably from 45 to 130 g/ha, yet more preferably from 60 to g/ha (e.g. 60, 90 or 120 g/ha), such as from from 60 to 90 g/ha; of the compound of formula (I) or a salt thereof (e.g. Compound no. 1 or 2, or a salt thereof), calculated as the free compound. "ha" = hectare.

Preferably, for application to (preferably application to the flood-waters of) transplanted rice (preferably transplanted flooded rice), the application rate for the compound of formula (I) or the salt thereof (e.g. Compound no. 1 or 2, or a salt thereof), is: from 30 to 250 g/ha, e.g. 60, 90, 120 or 240 g/ha; preferably from 50 to 180 g/ha or from 50 to 150 g/ha, e.g. 60, 90 or 120 g/ha; more preferably from 80 to 130 g/ha orfrom 90 to 120 g/ha, e.g. 90 or 120 g/ha; of the compound of formula (I) or a salt thereof (e.g. Compound no. 1 or 2, or a salt thereof), calculated as the free compound. "ha' = hectare.

-65 -In all aspects of the invention, the herbicidal composition (and/or compound of formula (I) or salt thereoO according to any aspect of the invention described herein (above or below) can also be used in combination with one or more safeners. The following mixtures with safeners, especially, come into consideration: [herbicidal composition of the invention, or compound of formula (I) or salt] + a compound of Me C+&NHMe the following formula: ° (herein named Safener no. 1") (e.g. as disclosed in EP 0 365 484 A -see e.g. compound 1.028 therein -or e.g. as disclosed in WO 2009/056333 or WO 2011/064533), [herbicidal composition of the invention, or compound of formula (I) or salt] + cyprosulfamide, [herbicidal composition of the invention, or compound of formula (I) or salt] + cloquintocet-mexyl, [herbicidal composition of the invention, or compound of formula (I) or salt] + cloquintocet acid or a salt thereof, [herbicidal composition of the invention, or compound of formula (I) or salt] + fenchlorazole-ethyl, [herbicidal composition of the invention, or compound of formula (I) or salt] + fenchlorazole acid or a salt thereof, [herbicidal composition of the invention, or compound of formula (I) or salt] + mefenpyr-diethyl, [herbicidal composition of the invention, or compound of formula (I) or salt] + mefenpyr diacid, [herbicidal composition of the invention, or compound of formula (I) or salt] + isoxadifen-ethyl, [herbicidal composition of the invention, or compound of formula (I) or salt] + isoxadifen acid, [herbicidal composition of the invention, or compound of formula (I) or salt] + furilazole, [herbicidal composition of the invention, or compound of formula (I) or salt] + furilazole R-isomer, [herbicidal composition of the invention, or compound of formula (I) or salt] + benoxacor, [herbicidal composition of the invention, or compound of formula (I) or salt] + dichlormid, [herbicidal composition of the invention, or compound of formula (I) or salt] + AD-67, [herbicidal composition of the invention, or compound of formula (I) or salt] + oxabetrinil, [herbicidal composition of the invention, or compound of formula (I) or salt] + cyometrinil, -66 - [herbicidal composition of the invention, or compound of formula (I) or salt] + cyometrinil Z-isomer, [herbicidal composition of the invention, or compound of formula (I) or salt] + fenclorim, [herbicidal composition of the invention, or compound of formula (I) or salt] + naphthalic anhydride, [herbicidal composition of the invention, or compound of formula (I) or salt] + flurazole, [herbicidal composition of the invention, or compound of formula (I) or salt] + CL 304,415, [herbicidal composition of the invention, or compound of formula (I) or salt] + dicyclonon, [herbicidal composition of the invention, or compound of formula (I) or salt] + fluxofenim, [herbicidal composition of the invention, or compound of formula (I) or salt] + DKA-24, [herbicidal composition of the invention, or compound of formula (I) or salt] + R-29148, or [herbicidal composition of the invention, or compound of formula (I) or salt] + PPG-1292.

The above-mentioned safeners are described, for example, in the Pesticide Manual, Twelfth Edition, British Crop Protection Council, 2000. R-29148 is described, for example by PB.

Goldsbrough et al., Plant Physiology, (2002), Vol. 130 pp. 1497-1 505 and references therein; and PPG-1292 is known from W02009/211761.

A safening effect is also thought to be possible for the mixtures of the compound of the formula (I) + dymron.

As a preferable safener, it is preferable for the herbicidal composition of the invention (or the compound of formula (I) or salt) to contain (or be mixed with) the compound of the following Me 1I1HO4YNHMe formula: 0 (herein named "Safenerno. 1"), or cyprosulfamide.

Preferably, the weight ratio of the compound of formula (I) or salt thereof (e.g. Compound no. 1 or 2, or salt thereof), calculated as the free compound, to the safener (e.g. the compound Me H /\H -. if 2

of formula 0 ° , orcyprosulfamide) is from 20:1 to 1:2, more -67 -preferably from 8:1 to 1:2 (e.g. 8:1,4:1 or2:1), still more preferablyfrom 4:1 to 1:1, e.g. 4:1 or 2:1.

According to a further aspect of the invention there is provided a herbicidal composition comprising: (a) a compound of formula (I) or an agriculturally acceptable salt thereof: R R (I), wherein the substituents within the compound of formula (I), and/or the compound of formula (I) or the salt thereof, are as defined herein (e.g. in the preferred embodiments thereof herein); and (b) an ALS (acetolactate synthase) inhibitor herbicide suitable for use on rice, wherein the rice-suitable ALS inhibitor herbicide is bensulfuron-methyl, pyrazosulfuron-ethyl, azimsulfuron, flucetosulfuron, orthosulfamuron, prosulfuron, triasulfuron, trifloxysulfuron, bispyribac, pyriminobac-methyl, pyribenzoxim, and/or penoxsulam, or an agriculturally acceptable salt of any of these; and (c) a safener which is a compound of the following formula: Me 0 or an agriculturally acceptable salt thereof or which is cyprosulfamide or an agriculturally acceptable salt thereof.

In this further aspect, preferably, the compound of formula (I) is a compound of formula (IA) or a compound of formula (IB), or an agriculturally acceptable salt thereof: -68 -(IA) (IB), wherein, in formula (IA), R1 is ethyl or cyclopropyl, and R2A is chlorine or fluorine.

In this further aspect, the weight ratio of the compound of formula (I) or the salt thereof, calculated as the free compound, to the rice-suitable ALS inhibitor herbicide. calculated as the free compound, is preferably as defined in the first aspect of the invention.

Preferably, the weight ratio of the compound of formula (I) or salt thereof (e.g. Compound no. 1 or 2, or salt thereoi, calculated as the free compound, to the safener (e.g. the compound Me

H H

S.. N NHMe of formula ° , or cyprosulfamide) is from 20:1 to 1:2, more preferably from 8:1 to 1:2 (e.g. 8:1, 4:1 or2:1), still more preferablyfrom 4:1 to 1:1, e.g. 4:1 or2:1.

The rate of application of safener in relation to herbicide depends largely on the method of application. In the case of field treatment, which is effected either using a tank mixture comprising a combination of safener and herbicide mixture or by separate application of safener and herbicide mixture, the ratio of the compound of formula (I) or salt (calculated as the free compound) to the safener is generally from 100:1 to 1:10, preferably from 20:1 to 1:1. In the case of field treatment, from 1 to 200 g of safener/ha, preferably from 5 to 100 kg of safener/ha, is generally applied.

In the composition according to the invention, the amounts of any oil additive which might be employed are generally from 0.01 to 2 %, based on the spray mixture. The oil additive can, -69 -for example, be added to the spray tank in the desired concentration after the spray mixture has been prepared.

Some non-limiting examples of the present invention are disclosed in the following Formulation Examples and/or Biological Examples.

-70 -

FORMULATION EXAM PLES

Formulation Example 1 -Emulsifiable concentrate (EC) formulation of Compound no. 1 (ECO5O formulation)

_________________________ ____________ ___________________ __________________ ________________

Ingredient (chemical Role Chemical name Grade Concentration structure/name or trade (g.r1) name) __________ ________________ _______________ ______________ Active I ingredient (Al) (Compound no. 1) __________ _______________ _______________ 50 Emulsifier castor oil 36 moles of ethoxylate ethylene oxide per mole of Emulsogen EL 360 TM castor oil 94.7 Emulsifier calcium salt of 63 % in dodecyl-benzene isobutanol Nansa EVM 63/B TM sulfonic acid _______________ 63.1 Emulsifier tristyrylphenol 16 moles of ethoxylate ethylene oxide per mole of Soprophor BSU TM __________ _______________ tristyrylphenol 31.6 Solvent N-octyl-2-N-octyl-2-pyrrolidone __________ pyrrolidone _______________ 210.5 2-ethyl hexanol Solvent 2-ethyl hexanol _______________ to 1 litre Formulation Example 2 -Emulsifiable concentrate (EC) formulation of Compound no. 2 (ECO5O formulation) Ingredient (chemical Role Chemical name Grade Concen-structure / name or trade tration (g11) name) __________ _________________ _______________ ____________ Active 50 uigredient (Compound no. 2) __________ ________________ ______________ ___________ -71 -Emulsogen EL 360 Emulsifier castor oil 36 moles of 84 4 ethoxylate ethylene oxide per mole of castor oil Nansa EVM63/B Emulsifier calcium salt of 63 % in 42 2 dodecyl-benzene isobutanol ________________________ __________ sulfonic acid _______________ ____________ acetophenone Solvent methyl-102.9 _________________________ ___________ phenylketone ________________ _____________ Solvesso 200 IM Solvent mixture of heavy ultra low to 1 litre aromatic naphthalene ________________________ __________ hydrocarbons content Formulation Example 3 -Emulsifiable concentrate (EC) formulation of Compound no. 3 (ECO5O formulation) Ingredient (chemical Role Chemical name Grade Concen-structure/name or trade tration (g.r1) name) ___________ _________________ ______________ _____________ Active ingredient (Compound no. 3) __________ ________________ _____________ 50 Emulsifier castor oil 36 moles of ethoxylate ethylene oxide per mole of Emulsogen EL 360 TM castor oil 95 Emulsifier calcium salt of 63 % in dodecyl-benzene isobutanol Nansa EVM 63/B TM sulfonic acid _____________ 63.3 Emulsifier tristyrylphenol 16 moles of ethoxylate ethylene oxide per mole of Soprophor BSU TM tristyrylphenol 31.7 Solvent N-octyl-2-N-octyl-2-pyrrolidone ___________ pyrrolidone ______________ 211.1 2-ethyl-hexanol Solvent 2-ethyl hexanol ______________ to 1 litre -72 -Emulsifiable concentrate (EC) procedure (used for Formulation Examples 1,2 and 3) The solvent(s) are added to the vessel, followed by the emulsifiers. The mixture is rolled until a clear solution is obtained. The active ingredient is then added, and rolled till a clear solution is obtained.

Formulation Example IA -Emulsifiable concentrate (EC) formulation containing Compound no. 1 and a rice-suitable ALS inhibitor herbicide (as defined herein) Formulation Example 1A is a variation of Formulation Example 1 in which, in the emulsifiable concentrate (EC), in addition to Compound no. 1, there is present a rice-suitable ALS inhibitor herbicide (which is bensulfuron-methyl, pyrazosulfuron-ethyl, azimsulfuron, flucetosulfuron, orthosulfamuron, prosulfuron, triasulfuron, trifloxysulfuron, bispyribac, pyriminobac-methyl, pyribenzoxim, and/or penoxsulam, or an agriculturally acceptable salt of any of these), and wherein Compound no. 1 and the rice-suitable ALS inhibitor herbicide are present in the following weight ratios: Formulation Example 1A: weight ratio of Compound no. ito the rice-suitable ALS inhibitor herbicide (each calculated as the free compound) is: 45:120, 60:120, 75:120, 90:120, 120:120, 45:90,60:90, 75:90, 90:90, 120:90, 45:60, 60:60, 75:60, 90:60, 120:60, 45:50, 60:50, 75:50, 90:50, 120:50, 45:30, 60:30, 75:30, 90:30, 120:30, 45:25, 60:25, 75:25, 90:25, 120:25, 45:20, 60:20, 75:20, 90:20, 120:20, 45:15, 60:15, 75:15, 90:15, or 120:15.

Formulation Example 2A -Emulsifiable concentrate (EC) formulation containing Compound no. 2 and a rice-suitable ALS inhibitor herbicide (as defined herein) Formulation Example 2A is a variation of Formulation Example 2 in which, in the emulsifiable concentrate (EC), in addition to Compound no. 2, there is present a rice-suitable ALS inhibitor herbicide (which is bensulfuron-methyl, pyrazosulfuron-ethyl, azimsulfuron, flucetosulfuron, orthosulfamuron, prosulfuron, triasulfuron, trifloxysulfuron, bispyribac, pyriminobac-methyl, pyribenzoxim, and/or penoxsulam, or an agriculturally acceptable salt of any of these), and wherein Compound no. 2 and the rice-suitable ALS inhibitor herbicide are present in the following weight ratios: -73 -Formulation Example 2A: weight ratio of Compound no. 2 to rice-suitable ALS inhibitor herbicide (each calculated as the free compound) is: 45:120, 60:120, 75:120, 90:120, 120:120, 45:90, 60:90, 75:90, 90:90, 120:90, 45:60, 60:60, 75:60, 90:60, 120:60, 45:50, 60:50, 75:50, 90:50, 120:50, 45:30, 60:30, 75:30, 90:30, 120:30, 45:25, 60:25, 75:25, 90:25, 120:25, 45:20, 60:20, 75:20, 90:20, 120:20, 45:15, 60:15, 75:15, 90:15, or 120:15.

Formulation Example 3A -Emulsifiable concentrate (EC) formulation containing Compound no. 3 and a rice-suitable ALS inhibitor herbicide (as defined herein) Formulation Example 3A is a variation of Formulation Example 3 in which, in the emulsifiable concentrate (EC), in addition to Compound no. 3, there is present a rice-suitable ALS inhibitor herbicide (which is bensulfuron-methyl, pyrazosulfuron-ethyl, azimsulfuron, flucetosulfuron, orthosulfamuron, prosulfuron, triasulfuron, trifloxysulfuron, bispyribac, pyriminobac-methyl, pyribenzoxim, and/or penoxsulam, or an agriculturally acceptable salt of any of these), and wherein Compound no. 3 and the rice-suitable ALS inhibitor herbicide are present in the following weight ratios: Formulation Example 3A: weight ratio of Compound no. 3 to the rice-suitable ALS inhibitor herbicide (each calculated as the free compound) is: 45:120, 60:120, 75:120, 90:120, 120:120, 45:90, 60:90, 75:90, 90:90, 120:90, 45:60, 60:60, 75:60, 90:60, 120:60, 45:50, 60:50, 75:50, 90:50, 120:50, 45:30, 60:30, 75:30, 90:30, 120:30, 45:25, 60:25, 75:25, 90:25, 120:25, 45:20, 60:20, 75:20, 90:20, 120:20, 45:15, 60:15, 75:15, 90:15, or 120:15.

-74 -

BIOLOGICAL EXAMPLES

Test plants (rice and weeds) were grown in a glasshouse (greenhouse) under hot and humid conditions, and the application of various herbicides and herbicidal mixtures were tested: -by post-emergence foliar spray application to rice or weeds (see Biological Example 1 below); and -by post-emergence application to the floodwaters of transplanted flooded rice or to the floodwaters of flooded weeds (see e.g. Biological Example 2 below).

Further, field trials have also been conducted on various compositions / mixtures of the compound of formula (I) with various rice-suitable ALS inhibitor herbicides (see e.g. Biological Example 3 et al).

Biological Example I -Glasshouse test for post-emergence foliar spray application of mixtures of compounds of formula (I) with either pyrazosulfuron-ethyl or halosulfuron-methyl, to rice or weeds (test 106) Biological Example I -Materials and Methods * Herbicide Arplication: Post-emergence foliar spray application, 300 LIha, single replicate * Climate: Standard rice conditions (hot and humid), in glasshouse. Specifically, the glasshouse bay conditions were 30°C/20°C day/night; 18/6 hours light/dark; 75% humidity.

* Rice: Rice seeds, variety IR-64 (an indica type of rice), were sown in seed trays. After about 7-8 days the resulting plants were transplanted into 6-inch-diameter circular pots with no holes containing Boughton loam soil, which was then was saturated with water replicating swampy conditions. The herbicide application took place when the rice was at the 3-leaf 1-tiller growth stage -this was 9 days after transplantation.

* Weeds: Long thin troughs with no holes, containing five weed species in five different positions side-by-side in Boughton loam soil, were used, as follows; the herbicidal application took place at the shown growth stages: * Echinochloa crus-galli (ECHCG) -2-3 leaves; this is a grassy monocotyledonous weed * Leptoch/oa chinensis (LEFCH) -2 leaves; this is a grassy monocotyledonous weed * Brachiaria p/antaginia (BRAPL) -2 leaves; this is a grassy monocotyledonous weed * Scirpusjuncoides (SCPJU) -2 leaves; this is an aquatic monocotyledonous sedge species in the family Cyperaceae (the sedges), -75 - * Monochoria vagina/is (MOOVA) -2 leaves; this is a monocotyledonous flowering plant in the water hyacinth family * Soil used for weeds and rice: Boughton loam (clay soil, pH 7.0, 5.9% OM), * Herbicidal compounds and compositions tested: * Compound no. 1 was tested in the form of ECO5O Formulation Example 1 * Compound no. 2 was tested in the form of ECO5O Formulation Example 2 * Compound nos. 1 and 2 were each tested at 15, 60, 90 & 120 g/ha on the weeds, and 60, 90,120 & 240 g/ha on the rice; and were each tested alone or in combination with: 21g/ha pyrazosulfuron-ethyl (WPO5 wettable powder formulation), or 20g/ha halosulfuron-methyl (WG75 water-dispersible granule formulation, marketed by Nissan under the trade marks PERMIT TM or SERVIAN TM) * In addition, a single rate of 90g/ha of each of Compound nos. 1 and 2 was tested in combination with a lower rate of each sulfonylurea: lOg/ha pyrazosulfuron-ethyl (WPO5 wettable powder formulation), or lOg/ha halosulfuron-methyl (WG75 water-dispersible granule formulation).

* The sulfonyl ureas were also tested alone at the higher rate (21g/ha pyrazosulfuron-ethyl, or 20g/ha halosulfuron-methyl).

* All herbicidal treatments were applied with the adjuvant Adsee at 0.2%v/v.

Biological Example I -Overview of the General Materials and Greenhouse (Glasshouse) Methods for Post-emergence Foliar Spray Application Rice seeds of variety IR-64 (an indica type of rice), were sown in seed trays. After about 7-8 days the resulting plants were transplanted into 6-inch-diameter circular pots with no holes containing Boughton loam soil. The loam soil in the rice pots was saturated with water replicating swampy conditions. The post-emergence foliar spray application of the herbicide(s) to the rice took place when the rice was at the 3-leaf 1-tiller growth stage -this was 9 days after transplantation and about 17 days after sowing.

The weeds, Echinoch/oa crus-ga/li (ECHCG), Leptoch/oa chinensis (LEECH), Bra chiairia plantaginea (BRAPL), Scirp us juncoides (SCPJU) and Monochoria vagina/is (MOOVA), were sown in seed trays (troughs) containing Boughton loam soil saturated with water, replicating swampy conditions. The rice and the weeds were then sprayed with the test herbicide(s) when they reached the growth stages mentioned above.

Glasshouse bay conditions were 30°C/20°C day/night; 18/6 hours light/dark; 75% humidity.

The test herbicidal solutions were prepared by mixing the appropriate aliquots of the test substance and adjuvant (Adsee at 0.2%v/v) in de-ionised water to give the desired treatment concentration.

-76 -The herbicidal application was made as a foliar spray, using a tracksprayer. 2 days after application the weed trays I troughs and rice pots were flooded to ca. 2-3 cm water depth, and maintained at this level for the duration of the test.

A visual assessment of the % herbicidal damage was made S and 15 Days After herbicide Application (DAA), and the results are presented herein as % visual herbicidal damage where 0 = no damage to plants and 100 = total kill.

Biological Example I -Some Specific Notes on Materials and Methods Actually Used 1. Weeds were initially grown in biodegradable troughs! trays, however these started leaking 1 week prior to spray application. The weeds along with soil they had rooted into were transferred with as little disturbance as possible, into plastic troughs. The weeds continued to grow well and did not appear to be checked in their growth due to this change.

2. The pots of rice and troughs!trays of weeds were mistakenly flooded 1-2 days prior to the herbicidal spray application. An attempt was made to remove this flood water (leaving wet swampy soil) just before the foliar spray application of the herbicide(s). Pots and troughs were then flooded 2 days after the spray application of the herbicide(s). The rice and weeds were then grown on, in the same hot and humid glasshouse conditions, and were generally watered once or twice daily, generally keeping the flood water at a depth of ca. 2 -3 cm in the pots and troughs.

3. The Scirpusjuncoides (SCPJU) controls varied, so any results of 0 to 40% phytotoxicity versus SCPJU should be treated with caution.

Biological Example I -Results 8 DAA (8 Days After herbicidal Application) Trends were similar at8 DAA to those described below at 15 DAA.

DAA (15 Days After herbicidal Application) The results at 15 DAA are illustrated in Table 1 below. A commentary then follows.

-77 -Table I -Biological Example I -Results (NT = not tested) Species and growth stage at application (numbers are % damage to the plant species ___________ __________ ________ ________ _______ ______ at 15 DAA) ______ ______ Applic-ation rate, Applic-comp-ation Rice Sulfonyl ound of rate, IR-64, ECH Compound urea formula sulfonyl 3 leaf CG, LEF BRA SOP MOO of formula mixture (I) (g / urea (g I & 1 2-3 CH, PL, JU, VA, (I) partner ha) ha) tiller leaf 2 leaf 2 leaf 2 leaf 2 leaf Compound no. 1 (ECOSO, Formulation Example 1) None 15 -NT 55 10 20 0 0 Compound no. 1 (ECO5O) None 60 -5 100 5 30 0 0 Compound no. 1 (EC050) None 90 -0 100 35 88 20 0 Compound no. 1 (ECO5O) None 120 -5 100 30 75 20 0 Compound no. 1 (ECOSO) None 240 -30 NT NT NT NT NT pyrazo- Compound sulfuron-no. 1 ethyl (ECOS0, VF05 Formulation formu-Example 1) lation) 15 21 NT 50 0 5 95 90 Compound pyrazo- no. 1 sulfuron- (EC0SO) ethyl 60 21 10 88 0 15 98 100 Compound pyrazo- no. 1 sulfuron- (ECO5O) ethyl 90 21 10 87 10 80 97 97 Compound pyrazo- no. 1 sulfuron- (ECO5O) ethyl 120 21 10 92 50 80 98 98 Compound pyrazo- no. 1 sulfuron- (ECO5O) ethyl 240 21 10 NT NT NT NT NT Compound halo- no. 1 sulfuron- (ECOS0, methyl Formulation G75 Example 1) formul-15 20 NT 55 0 20 100 80 -78 -ation) Compound halo- no. 1 sulfuron- (ECO5O) methyl 60 20 10 100 0 30 95 70 Compound halo- no. 1 sulfuron- (EC050) methyl 90 20 5 100 5 60 92 80 Compound halo- no. 1 sulfuron- (ECO5O) methyl 120 20 0 100 20 95 90 65 Compound halo- no. 1 sulfuron- (ECO5O) methyl 240 20 15 NT NT NT NT NT Compound pyrazo- no. 1 sulfuron- (ECOSO) ethyl 90 10 10 40 15 5 95 90 Compound halo- no. 1 sulfuron- (ECO5O) methyl 90 10 10 100 0 65 85 50 Compound no. 2 (ECO5O, Formulation Example2) None 15 -NT 75 0 10 10 0 Compound no. 2 (ECO5O) None 60 -0 100 5 78 20 0 Compound no. 2 (ECOSO) None 90 -0 100 5 92 10 0 Compound no. 2 (ECOSO) None 120 -0 100 5 98 90 0 Compound no. 2 (ECOSO) None 240 -0 NT NT NT NT NT pyrazo- Compound sulfuron-no. 2 ethyl (ECOSO, VF05 Formulation form-Example 2) ulation) 15 21 NT 50 0 30 95 100 Compound pyrazo- no. 2 sulfuron- (ECO5O) ethyl 60 21 0 100 0 40 90 100 Compound pyrazo- no. 2 sulfuron- (ECO5O) ethyl 90 21 5 100 0 80 95 99 Compound pyrazo- no. 2 sulfuron- (ECO5O) ethyl 120 21 0 100 10 94 97 96 -79 - Compound pyrazo- no. 2 sulfuron- (ECO5O) ethyl 240 21 10 NT NT NT NT NT halo- Compound sulfuron-no. 2 methyl (ECOSO, VG75 Formulation formul-Example 2) ation) 15 20 NT 50 0 0 90 88 Compound halo- no. 2 sulfuron- (ECO5O) methyl 60 20 5 100 15 78 80 65 Compound halo- no. 2 sulfuron- (ECO5O) methyl 90 20 5 100 10 93 95 93 Compound halo- no. 2 sulfuron- (ECO5O) methyl 120 20 0 100 30 93 93 80 Compound halo- no. 2 sulfuron- (ECO5O) methyl 240 20 10 NT NT NT NT NT Compound pyrazo- no. 2 sulfuron- (ECO5O, ethyl Formulation VF05

Example 2) form-

__________ ulation) 90 10 10 100 10 88 95 90 Compound halo- no. 2 sulfuron- (ECOSO, methyl Formulation G75

Example 2) formul-

__________ ation) 90 10 0 0 0 30 75 40 None pyrazo- S u If u ron-ethyl fP05 form u I- __________ ation) -21 10 45 10 20 97 90 None halo- s u If u ron-methyl ___________ (WG75) -20 5 25 0 30 95 88 Discussion of Results for Compound no. I at 15 DAA Rice: 24Oglha of Compound no. 1 caused 30% damage to the rice at 15 DAA. Neither of the sulfonyl ureas (21 g/ha pyrazosulfuron-ethyl or2og/ha halosulfuron-methyl) tested in combination with 240g/ha Compound no. 1 caused this much damage (maximum 15% -80 -phytotoxicity), thus implying they are having a safening effect. It should be noted that the score (30%) that this is based on was from just one pot of rice to which 24OgIha Compound no. 1 had been applied.

Weeds: Compound no. 1 alone achieved excellent control of ECHCG (100% herbicidal damage at 60-120g/ha), good herbicidal activity on BRAPL (approx 88-75% herbicidal damage) at 90- 120g/ha, only moderate herbicidal activity on LEFCH (approx 35-30% herbicidal damage) at 90-120g/ha, low herbicidal activity on SCPJU, and zero activity on MOOVA.

Addition of 21g/ha pyrazosulfuron-ethylto Compound no. 1 caused a slight reduction in ECHCG activity (reduced from 100% to 87-92%), had little effect on BRAPL activity, and had little effect on LEECH activity except that herbicidal damage appeared to be numerically increased from ca. 30% to Ca. 50% when used with 120g/ha of Compound no. 1.

Importantly, addition of 21g/ha pyrazosulfuron-ethyl to Compound no. 1 provided almost complete control of SCPJU (95-98%) and MOOVA (90-100%), unlike Compound no. 1 alone.

Addition of 20g/ha halosulfuron-methyl to Compound no. 1 did not reduce the herbicidal activity of Compound no. 1 against ECHCG, but was generally less effective than pyrazosulfuron-ethyl at controlling MOOVA. Eor example, 20g/ha halosulfuron-methyl + 120g/ha Compound no. 1 appeared to give 95% control of BRAPL but control of MOOVA had fallen to 65%.

The lower (10 g/ha) pyrazosulfuron-ethyl rate in admixture with 90g/ha Compound no. 1 gave results on SCPJU and MOOVA similar the those achived by the higher (21 g/ha) pyrazosulfuron-ethyl rate with 9Oglha Compound no. 1.

The lower (10 g/ha) halosulfuron-methyl rate in admixture with 90g/ha Compound no. 1 gave lower activity on the MOOVA than the higher (20 g!ha) halosulfuron-methyl rate in admixture with 90g/ha Compound no. 1.

Discussion of Results for Compound no. 2 at 15 DAA Rice: Compound no.2 alone showed no rice damage atlS-240g/ha. The addition of the sulfonyl ureas caused negligible damage.

-81 -Weeds: Compound no. 2 alone achieved excellent (100%) control of ECHCG at 60-120g/ha, and at 15g/ha the control remained quite good (75%) and was slightly better than that of Compound no. 1. Compound no. 2 alone also achieved good control of BRAPL (78%, 92%, 98% at 60, 120g/ha, slightly better than Compound no. 1), and 90% control of SCPJU at l2OgIha.

Addition of 21g/ha pyrazosulfuron-ethylto Compound no.2 improved Compound no. 2's weed spectrum by adding good-very good control of SCPJU and MOOVA.

Addition of 20g/ha halosulfuron-methyl to Compound no. 2 improved Compound no. 2's weed spectrum by giving good activity on SCPJU and quite good activity on MOOVA.

The lower (10 g/ha) pyrazosulfuron-ethyl rate in combination with 90g/ha Compound no. 2 appeared to give a slightly higher BRAFL herbicidal activity and a slightly lower MOOVA herbicidal activity than the higher (21 g/ha) pyrazosulfuron-ethyl rate + 90g/ha Compound no. 2.

Halosulfuron-methyl (lOg/ha) + 90g/ha Compound no.2 scores were inconsistent with respect to grass weed control, and thus are not considered here.

Discussion of Results for pyrazosulfuron-ethyl orhalosu/furon-methyl mixture partners at 15 DAtA 21g/ha pyrazosulfuron-ethyl alone gave good control of SCPJU and MOOVA. Application of 21g/ha pyrazosulfuron-ethyl with Compound no. 1 or Compound no. 2 gave good control of all of ECHCG, BRAPL, SCPJU and MOOVA (especially at 90-120g/ha of Compound no. 1 or 2), though LEFCH was still not fully controlled.

20g/ha halosulfuron-methyl alone gave good control of SCPJU and MOOVA. Addition of either Compound no. 1 or Compound no. 2 to the 20g/ha halosulfuron-methyl gave good or quite good control of ECHCG, BRAPL and SCPJU (especially at 120g/ha of Compound no. 1 and 60-120g/ha of Compound no. 2), though in these mixtures the MOOVA activity was often reduced compared to 20g/ha halosulfuron-methyl alone, and LEFCH was still not fully controlled.

-82 -

Biological Example I -Conclusions

In this glasshouse test, Compound no. 2 was safer to rice and slightly more active on the weeds (ECHCG, BRAPL and SCPJU) than Compound no. 1, under the glasshouse conditions tested.

There is the possibility of safening of Compound no. 1 damage to rice, especially at higher (e.g. 240 g/ha) application rates, by applying Compound no. 1 in mixture with pyrazosulfuron-ethyl or halosulfuron-methyl.

Mixtures of 60 to 240 g/ha of Compound no. 1 together with 21 g/ha of pyrazosulfuron-ethyl, and of 90 g/ha Compound no. 1 + log/ha pyrazosulfuron-ethyl, were observed to have low (10%) phytotoxicity on the IR-64 indica rice, under the glasshouse conditions tested.

Mixtures of 60 to 240 g/ha of Compound no. 2 together with 21 g/ha of pyrazosulfuron-ethyl, and of 90 g/ha Compound no.2 + lOg/ha pyrazosulfuron-ethyl, were observed to have low or very low (0-10%) phytotoxicity on the IR-64 indica rice, under the glasshouse conditions tested.

The weed-control spectrum of Compound no. 1 and Compound no. 2 is increased and improved (to include activity against SCPJU and MOOVA) by inclusion of each of the two sulfonyl urea mixture partners (pyrazosulfuron-ethyl or halosulfuron-methyl), with the pyrazosulfuron-ethyl-containing mixtures controlling MOOVA better than the halosulfuron-methyl-containing mixtures, under the glasshouse conditions tested. None of the mixtures fully controlled LEFCH.

It is also noted that each of Compound no. 1 and Compound no. 2 alone have post-emergent herbicidal activity against BRAPL.

-83 -Biological Example 2 -Glasshouse test for post-emergence floodwater application of mixtures of compounds of formula (I) with either pyrazosulfuron-ethyl or halosulfuron-methyl, to flooded transplanted rice orto flooded weeds (test 105) Biological Example 2 -Overview of the Materials and Methods of Greenhouse (glassho use) for the Transplanted Rice (TPR) System, as used in this test Rice seeds, variety IR-64 (an indica type of rice), were sown in seed trays. After about 7 days the resulting plants were transplanted as 3 groups of 2 plants, into 6-inch-diameter circular pots containing a loam soil (here, Boughton loam (clay, pH 7.0, S.907o OM)) saturated with water, replicating swampy conditions. These were grown on for a further 9 days in a glasshouse bay (under the following climatic conditions: 30/20°C day/night; 18/6 hours light/dark; 75% humidity).

The weeds, Echinoch/oa crus-galli (ECHCG), Fimbristy/is miliacea (FIMMO; Scirpus mahtimus (SCPMA) and Monochoha vagina/is (MOOVA) were sown in long thin seed trays (troughs), with the trays / troughs containing the different weed species in different positions side-by-side. The trays / troughs contained a loam soil (Boughton loam) saturated with water, replicating swampy conditions. The weeds were grown on in a glasshouse bay under the same climatic conditions as the rice.

All pots of rice and all trays / troughs of weeds were flooded to ca. 2-3 cm water depth on the day prior to application of the test herbicidal substances. The herbicidal treatments were applied 9 days after the rice was transplanted. Growth stages at time of herbicide application were as follows (note: activity vs ECHCG was tested at two different growth stages): IR-64 Rice: 2-3 leaves and 1 tiller ECHCG (section 1 of trays): 2-3 leaves MOOVA (section 2 of trays): 1-2 leaves FIMMI (section 3 of trays): 3 leaves ECHCG (section 4 of trays): 0.5 to 1 leaves (early growth stage of ECHCG) SCPMA (section 3 of trays): 3 leaves Test solutions were prepared by mixing the appropriate aliquots of the test substances in de-ionised water to give the desired treatment concentration.

-84 -Most of the test substances were used as formulated products. Specifically, Compound no. 1 was applied as the ECO5O formulation disclosed in Formulation Example 1 herein (EC = emulsifiable concentrate). Compound no. 2 was applied as the ECO5O formulation disclosed in Formulation Example 2 herein. Halosulfuron-methyl was used as a WG75 water-dispersible granule formulation, marketed by Nissan under the trade marks PERMIT TM or SERVIAN TM Pyrazosulfuron-ethyl was used as a WPO5 wettable powder formulation.

Application of the test substances was made by pipetting the required amount of the test solution or the test formulation gently into the flood water of the appropriate pot or tray/trough.

The test plants were then grown on in the same glasshouse conditions, and watered twice daily keeping the flood water at a depth of ca. 2 -3 cm.

A visual assessment of the % herbicidal damage was made 7 & 14 Days After Application of the herbicide(s) (DAA), and the results are presented herein as % visual heibicidal damage, where 0 = no damage to plants and 100 = total kill.

For the weeds and the rice, for each herbicidal compound or mixture, and for each application rate, only one rice pot and one weed tray/trough was used. That is, there were no replicates.

Biological Example 2 -Resu/ts The results at 14 DAA are illustrated in Table 2 below. A commentary then follows.

-85 -Table 2 -Biological Example 2 -Results (NT = not tested) The results below show % herbicidal damage to the plant species tested at 14 DAA.

Species and growth stage at application (numbers are % damage to the plant species at ________ _______ ______ ______ _____ _____ 14 DAA) ____ ____ appli- cation appli-rate for cation comp-rate for IR-64 ound of sulf-rice ECH MOO FIM ECH SCP Compound sulfonyl formula onyl 2-3 CG VA Ml CG MA of formula urea (l)(gI urea (g leaf, 1 2-3 1-2 3 0.5-1 3 (I) herbicide ha) I ha) tiller leaf leaf leaf leaf leaf Compound no. 1 (EC050, Formulation Example 1) none 60 -NT 80 0 5 100 0 Compound no. 1 (ECO5O) none 90 -15 85 0 5 98 0 Compound no. 1 (ECO5O) none 120 -20 100 0 5 100 0 Compound no. 1 (ECOSO) none 240 -35 NT NT NT NT NT Compound no. 1 (ECOSO) none 480 -55 NT NT NT NT NT pyrazo- Compound sulfuron-no. 1 ethyl (ECOSO, (WPOS Formulation formul-Example 1) ation) 60 21 NT 60 95 100 70 85 Compound pyrazo- no. 1 sulfuron- (ECOSO) ethyl 90 21 10 65 95 100 75 90 Compound pyrazo- no. 1 sulfuron- (ECOSO) ethyl 120 21 15 75 95 100 90 85 Compound pyrazo- no. 1 sulfuron- (ECOSO) ethyl 240 21 35 NT NT NT NT NT Compound pyrazo- no. I sulfuron- (ECOSO) ethyl 480 21 50 NT NT NT NT NT -86 - halo- Compound sulfuron-no. 1 methyl (ECO5O, G75 Formulation formul-Example 1) ation) 60 20 NT 30 95 95 55 90 Compound halo- no. 1 sulfuron- (ECO5O) methyl 90 20 20 60 90 100 65 M Compound halo- no. 1 sulfuron- (ECO5O) methyl 120 20 25 65 95 100 85 85 Compound halo- no. 1 sulfuron- (ECO5O) methyl 240 20 30 NT NT NT NT NT Compound halo- no. I sulfuron- (ECO5O) methyl 480 20 50 NT NT NT NT NT pyrazo- Compound sulfuron-no. I ethyl (ECO5O, P05 Formulation formul-Example 1) ation) 90 15 5 50 95 95 75 80 halo- Compound sulfuron-no. I methyl (ECO5O, G75 Formulation formul-Example 1) ation) 90 15 30 55 98 100 90 75 Compound no. 2 (ECO5O, Formulation Example 2) none 60 ________ NT 85 0 0 90 0 Compound no. 2 (ECOSO) none 90 _______ 10 98 0 5 100 0 Compound no. 2 (ECO5O) none 120 _______ 20 98 0 5 100 0 Compound no. 2 (ECO5O) none 240 _______ 20 NT NT NT NT NT Compound no. 2 (ECOSO) none 480 _______ 30 NT NT NT NT NT pyrazo- Compound sulfuron-no. 2 ethyl (ECOSO, (WPOS Formulation formul-Example 2) ation) 60 21 NT 60 95 98 75 90 -87 - Compound pyrazo- no. 2 sulfuron- (EC050) ethyl 90 21 5 70 95 98 75 90 Compound pyrazo- no. 2 sulfuron- (ECO5O) ethyl 120 21 5 100 95 98 95 90 Compound pyrazo- no. 2 sulfuron- (EC050) ethyl 240 21 25 NT NT NT NT NT Compound pyrazo- no. 2 sulfuron- (ECOSO) ethyl 480 21 30 NT NT NT NT NT halo- Compound sulfuron-no. 2 methyl (ECO5O, G75 Formulation formul-Example 2) ation) 60 20 NT 60 95 100 70 80 Compound halo- no. 2 sulfuron- (ECO5O) methyl 90 20 5 85 95 100 85 70 Compound halo- no. 2 sulfuron- (ECO5O) methyl 120 20 5 85 95 100 90 95 Compound halo- no. 2 sulfuron- (ECOSO) methyl 240 20 15 NT NT NT NT NT Compound halo- no. 2 sulfuron- (ECO5O) methyl 480 20 30 NT NT NT NT NT Compound no. 2 pyrazo- (ECOSO, sulfuron-Formulation ethyl Example 2) (WPO5) 120 15 5 70 100 95 90 90 halo- Compound sulfuron-no. 2 methyl (ECOSO) (WG7S) 120 15 NC* NC* NC* NC* NC* NC* pyrazo- sulfuron-ethyl (WPOS formul-none ation) -15 0 30 95 98 40 95 pyrazo- sulfuron-ethyl none (WROS) -21 5 40 95 98 40 95 halo- sulfuron-methyl none (WG75) -15 5 5 90 100 15 40 -88 - halo- sulfuron-methyl none (WG75) -20 10 5 80 100 5 80 NT = not tested. M = missing result.

* NC = results not considered. The results on the weeds for 120 g/ha of Compound no. 2 and 15 g/ha halosulfuron-methyl were clearly not consistent with other similar treatments, suggesting there may have been an error in chemical formulation for this specific treatment, and so the rice and weeds results have been removed and not considered where NC is shown.

Biological Example 2 -Comments on the results 1. Inclusion of pyrazosulfuron-ethyl as a mixture partner with either Compound no. 1 or Compound no. 2 gave a herbicidal composition with low or reasonably low (5-15%) rice phytotoxicity (damage), under the glasshouse conditions tested. See for example the reasonably low rice phytotoxicity results for: (a) 21 g/ha pyrazosulfuron-ethyl + 90-120 g/ha Compound no. 1, (b) 15 g/ha pyrazosulfuron-ethyl + 90 g/ha Compound no. 1, (c) 21 g/ha pyrazosulfuron-ethyl + 90-120 g/ha Compound no. 2, and (d) 15 g/ha pyrazosulfuron-ethyl + 120 g/ha Compound no. 2.

2. There is a slight indication that pyrazosulfuron-ethyl may slightly reduce rice phytotoxicity (damage) caused by 90-120g/ha Compound no. 1 or Compound no. 2, under the glasshouse conditions tested.

3. Inclusion of either pyrazosulfuron-ethyl or halosulfuron-methyl as a mixture partner with either Compound no. 1 or Compound no. 2 improved the weed control spectrum of Compound no. 1 or Compound no. 2 by achieving control of MOOVA, FIMMI and SCPMA, under the glasshouse conditions tested.

4. Compound no. 2 (alone or in mixtures) was generally less damaging to rice than Compound no. 1 (under comparable conditions, alone or in mixtures), under the glasshouse conditions tested.

-89 -Biological Example 3-Field Trial Results -Evaluation in the field of Compound no. I applied together with either pyrazosulfuron-ethyl or bensulfuron-methyl, for one-pass weed control in rice in Asia

Biological Example 3 -Summary

Weed control and crop tolerance of Compound no. 1 (using an EC 050 formulation similar or identical to Formulation Example 1) applied in combination with the sulfonyl urea rice herbicides pyrazosulfuron-ethyl and bensulfuron-methyl were evaluated by Syngenta, in a series of field trials in several countries in Asia. One advantage of combining active ingredients is to create products which will control grasses (grassy weeds) and broadleaved weeds to acheive broader spectrum weed control. In addition combinations with sulfonyl ureas ideally should retain flexibility re the timing of the herbicidal application.

As the field trial work continued, a further, unexpected, benefit of these mixtures became more and more obvious. These combinations exhibit an improved rice crop tolerance vs. the application of the Compound no. 1 alone.

The original objective of all these trials was the evaluation and eventually selection of the best partner for additional activity on broadleaved weeds and sedges. This brief report will focus on the additional benefit of improved rice crop tolerance which unexpectedly came obvious during the evaluations. The report uses the combination of Compound no. 1 and pyrazosulfuron-ethyl in transplanted rice as an example mixture. The same effect was also observed to be present with another sulfonyl urea rice herbicide, bensulfuron-methyl.

Biological Example 3-Introduction

Compound no. 1 is a grass weed herbicide discovered and developed by Syngenta, which is believed to work via inhibiting ACCase within grassy monocotyledonous weeds. Syngenta performed a series of field trials to evaluate the biological performance of combinations of Compound no. 1 with a certain sulfonylurea (pyrazosulfuron-ethyl or bensulfuron-methyl, seeking to acheive one-pass broad (or broader) spectrum weed control.

Objectives: * evaluate mixtures of Compound no. 1 applied as an EC 050 formulation in a tank mix with either pyrazosulfuron-ethyl or bensulfuron-methyl -90 - * describe rice crop tolerance, application window and weed spectrum of such tank mixes in wet sown rice and transplanted rice, * compare performance and behavior of different mixtures with standards Biological Example 3 -Materials, Methods and Locations 1. Locations Field trials were conducted in a number of South Asian and/or Asia-Pacific countries where rice is grown.

2. Material and Methods Abbreviations: WSR = wet sown rice, or wet-seeded rice.

DSFR = direct-seeded (or dry-seeded) flooded rice.

TPR = transplanted rice.

DATP = days after transplanting of the rice DAA = days after application of the herbicide(s) Product samples of Compound no. 1 were provided as formulated EC 050 formulations (e.g. Formulation Example 1 or a similar formulation), and were used in various rice cropping systems and in different application methods.

In transplanted rice the liquid EC (emulsifiable concentrate) formulation was diluted in 5 litres of water and injected via pipette into the paddy water (i.e. application to the floodwaters). In WSR and DSFR rice cropping systems, the formulations were diluted with the calculated amounts of water and sprayed with knapsack-sprayer. The applied product -water solutions were based on water volumes of 200-300 litres/ha.

The herbicides were generally applied at the following application rates: -120 g/ha Compound no. 1 (as a ECO5O formulation), tank mixed with 20 g/ha pyrazosulfuron-ethyl (as Sirius 250 SC or as Sirius 0,07 GR) -120 g/ha Compound no. 1 (as a ECO5O formulation), tank mixed with 50 g/ha bensulfuron-methyl (as Londax 60 DF or as Londax 80 WP) -91 -The field trials were layed out as randomized complete block systems with 3 replicates. Plot sizes varied from 10 to 25 qm. Results were recorded from trials with two/three replications.

The data describe the performance on indigenous weed infestations on the rice variety IR-64

(this rice variety was used in all field tests).

In the majority of cases the stage of the ECHCG (Fchinochloa crus-gal/i) weeds present guided the application timings. In transplanted rice generally the applications were carried out at one of the following three approximate timings: pre-emergence/very-early-post-emergence = 0-1 leaves = 3 DAIP, post-emergence = 2 -3 leaves = 10 DATP post-emergence = 3 -4 leaves = 15 DATP In transplanted rice the majority of trials were applied at DATP 10 which is very common application timing in practical rice farming. Foliar sprays in WSR and DSFR were applied as post-emergence applications to the 3 -5 leaves stages of ECHCG.

Trials were visually evaluated for phytotoxicity and efficacy at 7, 15, 30, 40-50 DAA. Records were taken in percent (%) damage to the crop resp. activity on the weeds. Ratings always compare to untreated plots.

The rice crop phytotoxicity values show the maximum scores of rice crop damage across all the crop phytotoxicity ratings (2-4 in the period of 7-45 days after transplanting) of a given treatment.

Biological Example 3-Results Biological Example 3-Rice Crop Tolerance Compound no. 1 + pyrazosulfuron-ethyl (Sirius 250 SC or as Sirius 0,07 GR) Rice Crop tolerance of Compound no. 1 applied alone as an EC5O can be critical. Compound no. 1 at 120 g/ha in light (sandy) soil conditions was seen to cause some transient stunting of the rice which can exceed acceptable limits. Taking in account all trials disregarding the soil -92 -factor we obtain some improvement in crop tolerance (ca. 3% to 4.5%) if Compound no. 1 was applied as a tank-mix with pyrazosulfuron-ethyl (see Table 2A below).

Table 2A: Maximum rice crop phytotoxicity scores (%) for Compound no. 1, or Compound no. 1 tank-mixed with pyrazosulfuron-ethyl, in transplanted rice DATP1O DATP15 DATP3 pyrazo-pyrazo-pyrazo- sulfuron-sulfuron-sulfuron-Compound Compound Compound ethyl + ethyl + ethyl + Trial Soil type no. 1 no. 1 no. 1 Compound Compound Compound no. I no. I no. 1 g/ha + 20 g/ha + 20 g/ha + 120g/ha 120g/ha l2OgIha 120g/ha l2OgIha 120 glha sandy 1 30.0 15.0 loam sandy 2 15.0 8.3 loam clay 3 16.0 15.0 loam clay 4 15.0 11.0 loam clay 8.3 11.7 loam clay 6 5.3 7.0 loam clay 7 0.0 0.0 loam clay 8 0.0 0.0 loam sandy 9 40.7 32.3 loam sandy 40.7 32.3 loam clay 11 47.5 45.0 loam 12 clay 32.5 27.5 -93 -loam clay 13 26.0 20.0 loam sandy 14 53.3 41.7 loam sandy 53.3 41.7 loam clay 16 0.7 1.3 loam clay 17 0.0 0.0 loam clay 18 5.0 11 loam clay 19 13.5 13.5 loam clay 11.0 13.5 loam Sum of max. rice 274.0 225.3 92.3 68.2 47.5 45.0 phytotoxicities Average of max. rice 24.9% 20.5% 11.5% 8.5% 47.5% 45.0% phytotoxicities Difference, in average of max. rice phytotoxicities, between Compound 4.4 % 3.0 % 2.5 % 1 alone and Compound 1 with pyrazosulfu ron-ethyl The improvement of the crop tolerance (reduction in crop phyto Idamage) with the mixtures is best expressed in light! sandy soil situations. In both application timings (DATP1O and DATP 15) -crop tolerance improves considerably. In clay loam soil conditions the differences in the phytotoxicity scores of Compound no. 1 alone and the mixture with pyrazosulfuron-ethyl is much less visible (see Tables 3, 4, 5, and 6 below).

-94 -Table 3: Maximum rice phytotoxicity scores (%) for Compound no. 1, or Compound no. 1 as a tank mix with pyrazosulfuron-ethyl, in transplanted rice in sandy soils at DATP 10 DATP 10 Difference Compound pyrazosulfuron-ethyl + Trial Soil type no. 1 Compound no. 1 g/ha 20 g/ha + 120 g/ha 2 sandy loam 15.0 8.3 6.7 9 sandy loam 40.7 32.3 8.3 sandy loam 40.7 32.3 8.3 14 sandy loam 53.3 41.7 11.7 sandy loam 53.3 41.7 11.7 Sum of max. rice 203.0 156.3 46.7 (difference) phytotoxicities Average of max. rice 40.6% 31.3 % 9.3 % (difference) phytotoxicities Table 4: Maximum rice phytotoxicity scores (%) for Compound no. 1, or Compound no. I as a tank mix with pyrazosulfuron-ethyl, in transplanted rice in sandy soils at DATP 15 DAIP 15 Difference Compound pyrazosulfuron-ethyl + Trial Soil type no. 1 Compound no. 1 g/ha 20 glha + 120 glha 1 sandyloam 30% 15% 15% Table 5: Maximum rice phytotoxicity scores (%) for Compound no. 1, or Compound no. 1 as a tank mix with pyrazosulfuron-ethyl, in transplanted rice in clay loam soils at DATP 10 DATF 10 Difference Trial Soil type Compound pyrazosulfuron-ethyl + no. 1 Compound no. 1 -95 -g/ha 20 g/ha + 120 g/ha 3 clay loam 16.0 15.0 1.0 clay loam 8.3 11.7 -3.3 7 clay loam 0.0 0.0 0.0 12 clay loam 32.5 27.5 5.0 16 clay loam 0.7 1.3 -0.7 19 clay loam 13.5 13.5 0.0 Sum of max. rice 71.0 69.0 2.0 phytotoxicities Average of max. rice 11.8% 11.5% 0.3% phytotoxicities Table 6: Maximum rice phytotoxicity scores (%) for Compound no. 1, or Compound no. I as a tank mix with pyrazosulfuron-ethyl, in transplanted rice in clay loam soils at DATP 15 DATP 15 Difference Compound pyrazosulturon-ethyl + Trial Soil type no. 1 Compound no. 1 g/ha 20 g/ha + 120 g/ha 4 clay loam 15.0 11.0 4.0 6 clay loam 5.3 7.0 -1.7 8 clay loam 0.0 0.0 0.0 13 clay loam 26.0 20.0 6.0 17 clay loam 0.0 0.0 0.0 18 clay loam 5.0 1.7 3.3 clay loam 11.0 13.5 -2.5 Sum of max. rice 62.3 53.2 9.2 phytotoxicities Average of max. rice 8.9% 7.6% 1.3% phytotoxicities -96 -Compound no. I + bensulfuron-methyl (Londax 60 OF or Londax 80 WP) The statements, regarding reduced rice crop phytotoxicity, made for the Compound no. 1 + pyrazosulfuron-ethyl mixture were found also to apply for the mixture of Compound no. 1 + bensulfuron-methyl. Again the advantage of the improved crop tolerance with mixture is more visible in light (sandy) soils (see Tables 7 and 8 below).

Table 7: Maximum rice phytotoxicity scores (%) for Compound no. 1, or Compound no. I in a tank mix with bensulfuron-methyl, in transplanted rice in all soils -all application timings All application timings Difference, in average of Compound pyrazosulfuron-ethyl + max. rice phytotoxicities, Trial Soil type no. 1 Compound no. 1 between Compound 1 alone and Compound 1 g/ha 20 g/ha + 120 g/ha with pyrazosulfuron-ethyl 1 sandy loam 30.0 15.0 15.0 2 sandy loam 15.0 2.7 12.3 3 clay loam 16.0 14.0 2.0 4 clay loam 15.0 10.3 4.7 S clay loam 8.3 13.3 -5.0 6 clay loam 5.3 5.3 0.0 9 sandy loam 40.7 36.7 4.0 sandy loam 40.7 36.7 4.0 11 clay loam 47.5 40.0 7.5 12 clay loam 32.5 30.0 2.5 13 clay loam 26.0 20.0 6.0 14 sandy loam 53.3 51.7 1.7 sandy loam 53.3 51.7 1.7 16 clay loam 0.7 3.0 -2.3 17 clay loam 0.0 0.0 0.0 18 clay loam 5.0 4.0 1.0 21 clay loam 12.5 0.0 12.5 22 clay loam 12.5 5.0 7.5 Sum of max. rice 414.3 339.3 75.0 (difference) phytotoxicities Average of max. rice 23.0% 18.9% 4.2% (difference) phytotoxicities -97 -Table 8: Maximum rice phytotoxicity scores (%) for Compound no. 1, or Compound no. 1 in a tank mix with bensulfuron-methyl, in transplanted rice in sandy soils -all application timings All application timings Difference, in average of Compound pyrazosulfuron-ethyl + max. rice phytotoxicities, Trial Soil type no. 1 Compound no. 1 between Compound 1 alone and Compound 1 g/ha 20 g/ha + 120 g/ha with pyrazosulfuron-ethyl 1 sandy loam 30.0 15.0 15.0 2 sandy loam 15.0 2.7 12.3 9 sandy loam 40.7 36.7 4.0 sandy loam 40.7 36.7 4.0 14 sandy loam 53.3 51.7 1.7 sandy loam 53.3 51.7 1.7 Sum of max. rice 233.3 194.4 38.7 (difference) phytotoxicities Average of max. rice 38.8 % 32.4 % 4.2 % (difference) phytotoxicities Biological Example 3-Weed control Weed control The performances of all of: Compound no. 1 at 120 g ai/ha, Compound no. 1 in a tank mix with pyrazosulfuron-ethyl, and Compound no. 1 in a tank mix with bensulfuron-methyl, on in particular Echinochloa crus-galli weeds was good.

The data set shows that despite achieving better rice crop tolerance with the two mixture products, the control of Echinochloa spp. reaches essentially the same level as Compound no. 1 alone.

The average % control (% herbicidal efficacy) on various weeds is shown in Table 9 below: Table 9 -Average weed control (% herbicidal efficacy) on various weeds, in transplanted rice, for all herbicidal application timings -for non-paired trials -98 -Compound bensulfuron-methyl + pyrazosulfuron-ethyl + Weed species no. 1 Compound no. 1 Compound no. 1 g/ha 50 g/ha + 120 g/ha 20 g/ha + 120 g/ha Cyperus difforniis 8 84 87 Echinochloa crus-ga/li 89 89 88 Fimbristy/is miliacea 0 91 37 Leptoch/oa chinensis 94 92 91 Ludwig/a adscendens 6 84 81 Mars/lea spp. 5 90 83 Monochoria spp. 0 90 94 Scirpus spp. 7 78 84 Sphenoc/ea zeylandica 11 88 83

Biological Example 3-Discussion and Conclusion

The mixtures of Compound no. 1 with pyrazosulfuron-ethyl or bensulfuron-methyl at application rates of 120g ai/ha of Compound no. 1 and 20g ai/ha of pyrazosulfuron-ethyl or 50g ai/ha bensulfuron-methyl (ai = Al = active ingredient), applied in a tank mix at application timings of 3 10 and 15 days after transplanting (DATP), show improved rice crop tolerance vs. Compound no. 1 alone at 120g al/ha. This is quite unexpected particularly if we take in consideration that the activity of the tank mixes on the key grass weed EchinochIoa crus-gaI/i remains on the same level achieved by Compound no. 1 alone. In consequence this unexpected improvement in rice crop tolerance of the mixtures probably cannot be explained with an antagonistic effect (in the rice) of the sulfonylurea Al to the Compound no. 1 if mixed and applied on the same time. Instead there appears to be an interaction of Compound no. 1 and the sulfonyl urea, related to uptake or translocation in the plant.

Finally, it can be stated that both sulfonyl urea herbicides add activity on a range of broadleaved weeds and sedges. Hence-the mixture of Compound no. 1 combined with either pyrazosulfuron-ethyl or bensulfuron-methyl, at an appropriate application rate, provides broad-spectrum weed control in a "one-shot" (one-pass) herbicidal application.

-99 -Biological Example 4-Field Trial Results -Evaluation in the field of Compound no. I applied together with pyrazosulfuron-ethyl, in transplanted rice

Materials and Methods of Field Trialing

The field trials within Biological Example 4 were carried-out during three different rice growing seasons in a South Asian country where rice is grown. The trial sites were selected in traditional rice growing tracts with known hot spots for infestation of target weeds (Echinochloa spp.) and with different soil types. An overview of the locations is reported in

the Table 10.

Table 10 -Overview of locations where the field trials of Biological Example 4 were carried out and their main soil characteristics. % CEC

Location Soil % Sand % Clay % Silt pH Organic (meq/100 Texture _________ __________ _________ _______ _________ ______ matter gr) Location Sandy 20 20 6.3 0.53 19.2 1 clay loam _________ _______ _________ ______ ________ _________ Location Loam 43 23 34 6.9 0.65 18.2 2 ____________ ___________ _________ ___________ ________ __________ ___________ Location Sandy 15 20 6.6 0.85 15.8 3 Loam _________ _______ _________ ______ ________ _________ Location Clay 40 30 6.5 0.78 43.7 4 loam ________ _______ ________ ______ ________ ________ Location Clay 33 38 29 7.4 0.68 19.1 loam _________ _______ _________ ______ ________ _________ Location Clay 32 43 25 7.2 0.76 22.4 6 ___________ __________ ________ __________ _______ __________ __________ The cropping system adopted in those trials was transplanted rice which consists to grow rice first in nursery area and then transplant the young seedlings in the open field. For this system 40-60 kg of pre-soaked seeds of different rice varieties, depending on the location, were sown in a nursery area (about 800 m2) for 25-30 days. When rice plants reached the 2-3 leaf stage they were uprooted and manually transplanted in the open field.

The experimental design followed was a Randomized Block Design (RBD) with 2-3 replications depending on the protocol requirements. 10 m2 (3.00 x 3.33 m) plots were prepared from the field previously ploughed, puddle and leveled. Each plot was provided by inlet and out for a proper water management and was isolated by channels to avoid cross contaminations between different treatments.

In the plot prepared as described above, 25-30 days old seedlings were manually transplanted following spacing of 25 x 20 cm. After transplanting any plot leveling was carried-out if needed.

The herbicide treatments were performed either at 10 days or at 15 days after transplanting, corresponding to an early-post and a post emergence application, respectively.

The chemicals were applied into the floodwater by using a pipette. All liquid formulations were pre-diluted in water in a separate vessel by using a water volume of 10 litres/ha and injected in to the respective plots at 8-10 places/plot to ensure a uniform coverage. At the time of application, the water (floodwater) level was maintained at 5 cm.

A ECO5O formulation (EC = emulsifiable concentrate) of Compound no. 1 was applied either alone, or in a tank mixture with the following herbicide safener Me C1H&NHMe 0 0 -herein named "Safenerno. 1", as a 50100 formulation: SC = suspension concentrate), or in a tank mixture with Safener no. 1 and the broadleaved-weed-herbicide partner (pyrazosulfuron-ethyl, as a WP1O formulation, WP = wettable powder). More details about the treatments are reported in Table 11 below.

-101 -Table 11: Herbicide treatments adopted in the field trials of Biological Example 4 (ai = active ingredient).

Compound/s Formulation Application Rates used __________________________________ __________________ (g ai I ha) Compound no. 1 ECO5O (i) 60 (ii) 90 ______________________________________________ ________________________ (üi) 120 Compound no. 1 + Safener no. 1 EC050 + SC100 (i) 60 + 30 (ii) 90 + 45 ________________________________ _________________ (iiQl2O + 60 Compound no. 1 + Safener no. 1 + ECO5O + SC100 + (i) 60 + 30 + 21 pyrazosulfuron-ethyl WP1O (ü) 90 + 45 + 21 The weed control and crop tolerance were assessed at regular intervals, generally at 5, 10, and 40 DAA (days after application of the herbicide). A visual assessment compared to untreated check was adopted. A scale from 0 to 100% was used, where 0 means no damage and 100% means dead crop or weed plants. However, for the discussion of the results only the peak of rice damage observed in the trials was reported, which represented the most critical data point and in most of the cases the crop fully recovered during the trial. Similarly, for the weed control only the last assessment (generally 40 or 50 DAS) was considered in the discussion being the most representative for the herbicidal efficacy.

Ordinary maintenance practices were carried-out during the trials. Green manure 5 t/ha was applied at the time of land preparation, in main field, followed by NPK fertilizer (nitrogen + phosphorus + potassium containing fertilizer) applications during different stages of the rice according to the local practices. Insect and disease control was carried out as local practices.

During the trial water level was carefully managed. At the time of transplanting and up to 7 days 2 cm depth of water level was maintained and after that, 3-5 cm water level was maintained throughout trial period.

-102 -

Field Results -Crop Tolerance and Weed Control

The results of crop tolerance and weed control for the different locations, soil types and timings are repoited in Table 12 below. The rice crop tolerance is expressed as the maximum level of phytotoxicity observed in each trial (this is a conservative risk-averse way of analysing I measuring crop phytotoxicity -the actual average % phytotoxicity will generally be lower). The weed control indicates the efficacy against Echinoch/oa spp. (ECHss) (mainly Echinochloa crus-ga/Ii, but also Echinochloa column in one trail) and the latest assessment timing available (generally 40-50 DAA) (DAA = days after application of the herbicide) was considered in the following elaboration.

Table 12: Results of field trails across different locations, soil types and rates of Compound no. 1 solo (alone) or in mixture with other herbicide and/or safener partners (ai = active ingredient).

Appli-Loca-Soil Compound(s) Appli-Maxi-ECHSS cation tion type cation mum control Timing Rate(s) Rice at the (DATp (g ai/ha) Phyto-latest = days toxicity assess-after (%) ment (%) trans-plant) _________ _________ _______________________ ____________ ___________ ___________ Loca-Sandy Compound no. 1 60 25 73 tion 1 clay 90 28 90 loam 120 35 94 Compound no. 1 + 60+30 28 75 Safener_no._1 ___________ __________ __________ ____________________ 90+45 25 88 120+60 33 93 Compound no. 1 + Lii Safenerno. 1 + 60+30+21 10 91 pyrazosulfuron-ethyl ____________ ___________ ___________ _______ _______ ___________________ 90+45+21 15 95 Loca-Loam Compound no. 1 60 0 53 LU tion2 90 0 88 F __________________ 120 0 100 Compound no. 1 + 60+30 0 58 c Safener no. 1 90+45 0 90 ___________________ 120+60 0 93 Compound no. 1 + Safenerno. 1 + 60+30+21 0 85 pyrazosulfuron-ethyl ____________ ___________ ___________ 90+45+21 0 95 Loca-Clay Compound no. 1 60 3 73 tion 4 loam 90 4 88 12 90 Compound no. 1 + 120+60 10 91 Safener no. 1 Compound no. 1 + Safener no. 1 + 60÷30+21 3 85 pyrazosulfuron-ethyl ____________ ___________ ___________ 90+45+21 3 91 Loca-Sandy Compound no. 1 60 16 80 tion 3 Loam 90 20 95 27 99 Compound no. 1 + 120+60 24 80 Safener_no._1 ___________ __________ __________ Compound no. 1 + Safenerno. 1 + 60+30+21 11 83 pyrazosulfuron-ethyl ____________ ___________ ___________ ________ ________ ____________________ 90+45+21 14 98 Loca-Clay Compound no. 1 60 0 80 tion6 90 3 89 ___________________ 120 8 98 Compound no. 1 + 120+60 3 93 Safener_no._1 ___________ __________ __________ Compound no. 1 + Safenerno. 1 + 60+30+21 2 89 pyrazosulfuron-ethyl ____________ ___________ ___________ 90+45+21 3 90 Loca-Clay Compound no. 1 60 0 78 tion 5 loam 90 3 85 ___________________ 120 9 93 Compound no. 1 + 120+60 8 90 Safener_no._1 ___________ __________ __________ Compound no. 1 + Safenerno. 1 + 60+30+21 3 80 _________ pyrazosulfuron-ethyl ____________ ___________ ___________ 90+45+21 4 90 Loca-Sandy Compound no. 1 60 10 68 a tionl clay 90 15 90

C loam

c 120 23 92 Compound no. 1 + 60+30 13 65 LU Safener no. 1

__________________________________________________________________________ __________ __________________________________________________________________________ __________________________________________________________________________

W 90+45 15 82 0 ______________________ ___________ __________ __________ 120+60 23 92 a F-Compound no. 1 + Safenerno. 1 + 60+30+21 13 91

C

pyrazosulfuron-ethyl ___________ __________ __________ -. 90+45+21 18 95 -104 -Loca-Loam Compound no. 1 60 0 45 tion2 90 0 80 0 98 Compound no. 1 + 60+ Safener_no._1 ___________ __________ __________ 90+45 0 98 120+60 0 98 Compound no. 1 + Safenerno. 1 + 60+30+21 0 95 pyrazosulfuron-ethyl ____________ ___________ ___________ 90+45+21 0 95 Discussion of Early Post-emergence results (application 10 days aftertransplant) Good Echinochloa control was achieved with 90 g al/ha of Compound no. 1. The addition of Safener no. 1, in the (weight) ratio 2:1 of Compound no. 1: Safener no. 1, generally did not have a great visible impact on rice crop tolerance or efficacy on Echinochloa, while the three way mixture Compound no. 1 + Safener no. 1 + pyrazosulfuron-ethyl showed a clear improvement of the efficacy even at lower application rates (i.e. 60+30+21 g ai/ha) (ai = active ingredient).

The rice crop tolerance was variable depending on the application rates of Compound no. 1 and particularly on the soil types. In most of the cases, the treatments including Compound no. 1 were sufficiently safe with a (maximum) crop injury within the commercially acceptable level (i.e. < 15%). A few exceptions, with (maximum) damage to rice greater than 20%, were observed for the Compound no. 1 treatments, as solo (alone) or mixed with Safener no. 1, in sandy soils. However, under the same soil conditions, the three way mixture Compound no. 1 + Safener no. 1 + pyrazosulfuron-ethyl was always sufficiently safe and gave good Echinochloa control.

Discussion of Post-emergence results (application 15 days after transplant) g ai/ha of Compound no. 1 gave very good Echinochloa control. The addition of safener Safener no. 1 to Compound no. 1, in the (weight) ratio 2:1 of Compound no. 1: Safener no. 1, improved the level of grass control in one location (Location 2 with Loam soil, at 60+30 g/ha and 90+45 g/ha of Compound no. 1 + Safener no. 1) but not in the other location. The effect was particularly visible at the lowest application rate where the Echinochloa control increased from 45% with 60 g ai/ha of Compound no. ito 60% with 60 g ai/ha of Compound no. 1 plus 30 g ai/ha of Safener no. 1 (ai = active ingredient). The three-way mixture Compound no. 1 + Safener no. 1 + pyrazosulfuron-ethyl resulted in a substantial improvement in Echinochloa control across application rates and locations.

The rice crop tolerance was variable depending mainly on the location and soil types. In sandy clay loam the level of (maximum) damage to rice was higher reaching 23% at 120 g ai/ha of Compound no. 1. However the three way mixture Compound no. 1 + Safener no. 1 + pyrazosulfuron-ethyl gave a noticeable improvement of the margin of rice selectivity by delivering a good level of Echinochloa control already at the rate of 60 g ai/ha Compound no. 1 +30 g ai/ha Safener no. 1 + 21 g ai/ha pyrazosulfuron-ethyl (ai = active ingredient).

A close look at all the field results showed that there was a clear pattern between the crop tolerance and the soil type, where the higher the soil sand content was, the higher the risk of crop injury. The results shown in Table 12 above can be used to correlate the maximum phytotoxicity observed in the different trials with the % of sand content of soils. Whilst Compound no. 1 applied alone (solo) at 60 and 90 g ai/ha was injurious on rice up to 28% (maximum rice phytotoxicity) in soils with more than 60% of sand, the three way mixture of Compound no. 1 + Safener no. 1 + pyrazosulfuron-ethyl gave no more than 18% of (maximum) rice phytotoxicity in the same extreme soil conditions, demonstrating a clear safening effect.

-106 -Biological Example 5 -Root uptake study in Laboratory -growing rice and Echinochloa in a hydroponic system Materials and Methods This root uptake study consists in growing rice and Echinochloa in a hydroponic system. For this type of study the procedures below were followed.

The tops of SmI amber vials were covered with Nescofilm and SmI of 1⁄4 strength Hoaglands solution (pH 5) was added to each vial. Pre-grown rice (md/ca variety, lR-64) and Ech/noch/oa crus-ga//i seedlings (2 leaf stage) were placed on top of the vials, ensuring that the roots were submerged in the solution. Particular care was taken in avoiding to damage the root system. The vials were then transferred to the Controlled Environment (C.E.) room at 24/18°C (day/night) for 24/48 hours to acclimatize prior to treatment.

The treatment solution was applied directly into the vials and the vials so treated were left in the CE. room until required for sampling. The Table 13 below summarizes the rates for each chemical.

Table 13: Treatment list used for the rice and Echinochloa root uptake studies.

Compound Formulation Concentration of Volume applied stock solution(s) in the vial (ppm = parts per (microlitres) ___________________________ ___________ million) ________________ Compound no. 1 ECO5O 1000 ppm 80 p1 Pyrazosulfuron-ethyl WPO5O 1000 ppm 20 p1 Safener no. 1 SC100 1000 ppm 40 p1 Compound no. 1+ ECO5O + 1000 ppm and 80 p1 + 20 p1 pyrazosulfuron-ethyl WPO5O 1000 ppm _______________ Compound no. 1 + Safener no. ECO5O + 1000 ppm and 80 p1 + 40 p1 1 SC100 1000 ppm _____________ Compound no. 1 + Safener no. ECO5O + 1000 ppm, 1000 80 p1 + 40 p1 + 20 1 + pyrazosulfuron-ethyl SC100 + ppm and 1000 p1 ___________________________ WPOSO ppm ________________ Samples were taken at time zero, 20, 40, 60 and 180 minutes after the chemical application.

For each time point six replicates were taken. Samples were removed from the amber vial and the roots were washed in solvent (80:20 acetonitrile:water), blotted dry and placed on a tray. The roots were separated from the shoot tissue and weighed individually. The samples were transferred to fast preparation tubes containing imI of solvent, macerated and centrifuged. The supernatant was withdrawn and transferred to an HPLC (high pressure/performance liquid chromatography) vial for analysis on the LCMS (liquid chromatography -mass spectrometry) apparatus.

Biological Example 5 -Laboratory Results -Rice and Echinochloa Root Uptake Interestingly, the ancillary laboratory studies on root uptake shed some light on the possible mechanism associated with the unexpected safening effect of three way mixture Compound no. 1 + Safener no. 1 + pyrazosulfuron-ethyl seen in Biological Example 4.

A hydroponic system was used to investigate the root uptake in rice and Echinochloa of different treatments with Compound no. 1 solo (alone) and in two or three way mixture with Safener no. 1 and/or pyrazosulfuron-ethyl. The results in Table 14 below showed a differential root uptake between rice and Echinochloa, where rice tended to absorb more chemical than Echinochloa. There were no clear differences in the root uptake in Echinochloa over the different chemical treatments. On the other hand, a treatment effect was noticed in rice, where the root uptake was highest when Compound no. 1 was applied with Safener no. 1. The peak of uptake was observed 1 hour after application, so much earlier than for the other treatments. Mixing Compound no. 1 with pyrazosulfuron-ethyl resulted in a reduction of up to five-fold of the root uptake into rice. Thus, a great reduction of root uptake in rice by pyrazosulfuron-ethyl could explain the safening effects (i.e. reduced rice phytotoxicity) shown in the field (see Biological Example 4 and also Biological Example 3) with the three way mixture of Compound no. 1 + Safener no. 1 + pyrazosulfuron-ethyl.

Table 14: Results of rice and Echinochloa root uptake with different chemical treatments and different sampling points.

______________________________ Sampling time (minutes after chemical application) ________________________________ 0 20 40 60 180 ________________________________ pg (micrograms) of Comoound no. 1 / root fresh weight in Rice Compound no. 1 solo (alone) 17.8 123.8 119.5 144.9 130.8 Compound no. 1 i-Safener no. 1 27.4 161.5 180.7 265.2 162.6 Compound no. 1 + pyrazosufluion-ethyl 14.0 22.4 28.3 25.6 29.9 Compound no. 1 + Safener no. 1 + pyrazosufluion-ethyl 15.5 22.9 24.1 22.3 28.6 pg (micrograms) of Compound no. 1/root fresh weight in __________________________________ ___________ _____________ Echinoohloa ___________ ___________ Compound no. 1 solo (alone) 1.5 9.0 10.1 11.6 21.2 Compound no. 1 + Safenei no. 1 3.4 8.4 10.0 12.0 20.3 Compound no. 1 + pyrazosufluron-ethyl 2.1 6.3 11.4 10.4 15.1 Compound no. 1 + Safener no. 1 + pyrazosufluron-ethyl 4.0 8.5 12.0 16.6 16.5

Claims (30)

1. CLAIMS: 1. A herbicidal composition comprising: (a) a compound of formula (I) or an agriculturally acceptable salt thereof: R R (I), wherein: R1 is methyl, ethyl, n-propyl, cyclopropyl, fluorine, chlorine, bromine, difluoromethoxy or trifluoromethoxy; R2 is phenyl or phenyl substituted by 1, 2 or 3 (e.g. 1 or 2) substituents independently being halogen, C1-C2 alkyl, C1-C2 fluoroalkyl, C1-C2 alkoxy, C1-C2 fluoroalkoxy or cyano; and either R4, R5, R6 and R7, independently of each other, are hydrogen, C-C alkyl, n-butyl or C1-C2alkoxyC1-C2alkyl; or R4 and R7 together are methanediyl, ethane-1,2-diyl or propane-i,3-diyl each of which is optionally substituted by one or two methyl substituents, or R4 and R7 together are ethene- 1,2-diyl optionally substituted by one or two methyl substituents; and R5 and R6, independently of each other, are hydrogen, C1-C3 alkyl, n-butyl or C1-C2alkyoxyC1-C2alkyl; and G is hydrogen, an alkali metal, alkaline earth metal, sulfonium, or ammonium, orG is C(c)Ra or C(O)ORUJ; wherein R is H, C1-C18alkyl, C2-C18alkenyl, C2-C13alkynyl, C1-C10fluoroalkyl, C2- C5fluoroalkenyl, C3-C3cycloalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C1-C10aminoalkyl, C- C5alkylaminoC1-C5alkyl, CC8dialkylaminoC1-C5alkyl, C3-C7cycloalkylC1-C5alkyl, C1- C5alkoxyC1-C5alkyl, (CC4alkenyl-methoxy)C1-C5alkyl, (C2-C4alkynyl-methoxy)C1-C5alkyl, C1- C5alkylthioC1-C5alkyl, C1-C5alkylsulfinylC1-C5alkyl, C1-C5alkylsulfonylC1-C5alkyl, C2- C3alkylideneaminoxyC1-C5alkyl, C1-C5alkylcarbonylC1-C5alkyl, C1-C5alkoxycarbonylC1- C5alkyl, aminocarbonylC1-C5alkyl, C1-C5alkylaminocarbonylC1-C5alkyl, C2- C8dialkylaminocarbonylC1-C5alkyl, C1-C5alkylcarbonylaminoC1-C5alkyl, N-C1-C5alkylcarbonyl-N-C1-C5alkylaminoC1-C5alkyl, C3-C3trialkylsilylC1-C5alkyl, phenylC1-C5alkyl (wherein the phenyl is optionally substituted by 1,2 or3 (e.g. 1)substituents independently being C-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, fluorine, chlorine, bromine, cyano, or nitro), heteroarylC1-C5alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or 3 (e.g. 1) substituents independently being C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, fluorine, chlorine, bromine, cyano, or nitro); phenyl or phenyl substituted by 1, 2 or3 (e.g. 1) substituents independently being C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro; or heteroaryl or heteroaryl substituted by 1,2 or3 (e.g. 1) substituents independently being C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro; and Rb is C1-C15alkyl, C2-C17alkenyl-CH2-, CrCi6alkenyl-CHMe-, CrCi5alkenyl-CMe2-, Cr C17alkynyl-CH2-, CrCi6alkynyl-CHMe-, CrCi5alkynyl-CMe2-, C2-C10fluoroalkyl, 02- C4fluoroalkenyl-CH2-, C2-C3fluoroalkenyl-CHMe-, C2fluoroalkenyl-CMe2-, C3-C8cycloalkyl, C- C10cyanoalkyl, C1-C10nitroalkyl, C2-C10aminoalkyl, C1-C5alkylaminoC1-C5alkyl, C2- C3dialkylaminoC1-C5alkyl, C3-C7cycloalkylC1-C5alkyl, C1-C5alkoxyC1-C5alkyl, (C2-C4alkenyl- methoxy)C1-C5alkyl, (C2-C4alkynyl-methoxy)C1-C5alkyl, C1-C5alkylthioC1-C5alkyl, C1- C5alkylsulfinylC1-C5alkyl, C1-C5alkylsulfonylC1-C5alkyl, CrCsalkylideneaminoxyCi-Csalkyl, C1- C5alkylcarbonylC1-C5alkyl, C1-C5alkoxycarbonylC1-C5alkyl, aminocarbonylC1-C5alkyl, C1- C5alkylaminocarbonylC1-C5alkyl, CrCedialkylaminocarbonylCi-Csalkyl, Ci- C5alkylcarbonylaminoC1-C5alkyl, N-C1-C5alkylcarbonyl-N-C1-C5alkylaminoC1-C5alkyl, C3-C5trialkylsilylC1-C5alkyl, phenylC1-C5alkyl (wherein the phenyl is optionally substituted by 1,2 or 3 (e.g. 1) substituents independently being C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, fluorine, chlorine, bromine, cyano, or nitro), heteroarylC1-C5alkyl (wherein the heteroaryl is optionally substituted by 1, 2 or3 (e.g. 1) substituents independently being C-C3alkyl, 01-C3fluoroalkyl, 01-C3alkoxy, C1-C3fluoroalkoxy, fluorine, chlorine, bromine, cyano, or nitro); phenyl or phenyl substituted by 1, 2 or 3 (e.g. 1) substituents independently being C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro; or heteroaryl or heteroaryl substituted by 1, 2 or 3 (e.g. 1) substituents independently being C1-C3alkyl, C1-C3fluoroalkyl, C1-C3alkoxy, C1-C3fluoroalkoxy, fluorine, chlorine, bromine, cyano or nitro; and (b) an ALS (acetolactate synthase) inhibitor herbicide suitable for use on rice, wherein the rice-suitable ALS inhibitor herbicide is bensulfuron-methyl, pyrazosulfuron-ethyl, azimsulfuron, flucetosulfuron, orthosulfamuron, prosulfuron, triasulfuron, trifloxysulfuron, bispyribac, pyriminobac-methyl, pyribenzoxim, and/or penoxsulam, or an agriculturally acceptable salt of any of these; and wherein the weight ratio of the compound of formula (I) or the salt thereof, calculated as the free compound, to the rice-suitable ALS inhibitor herbicide, calculated as the free compound, is as follows: if bensulfuron-methyl or a salt thereof is present, then the weight ratio of the compound of formula (I) to bensulfuron-methyl is from 180:20 to 10:120, orfrom 150:20 to 10:120; if pyrazosulfuron-ethyl or a salt thereof is present, then the weight ratio of the compound of formula (I) to pyrazosulfuron-ethyl is from 180:7 to 10:60, or from 150:7 to 10:60; if azimsulfuron or a salt thereof is present, then the weight ratio of the compound of formula (I) to azimsulfuron is from 180:7 to 10:50, or from 150:7 to 10:50; if flucetosulfuron or a salt thereof is present, then the weight ratio of the compound of formula (I) to flucetosulfuron is from 180:7 to 10:60, or from 150:7 to 10:60; if orthosulfamuron or a salt thereof is present, then the weight ratio of the compound of formula (l)to orthosulfamuron is from 180:15 to 10:150, or from 150:15 to 10:150; if prosulfuron or a salt thereof is present, then the weight ratio of the compound of formula (I) toprosulfuron isfrom 180:4to 10:60, orfrom 150:4to 10:60; if triasulfuron or a salt thereof is present, then the weight ratio of the compound of formula (I) to triasulfuron is from 180:1.5 to 10:20, or from 150:1.5 to 10:20; if trifloxysulfuron or a salt thereof is present, then the weight ratio of the compound of formula (I) to trifloxysulfuron is from 180:1.5 to 10:100, or from 150:1.5 to 10:100; if bispyribac or a salt thereof is present, then the weight ratio of the compound of formula (I) tobispyribacisfrom 180:lOto 10:70, orfrom 150:lOto 10:70; if pyriminobac-methyl or a salt thereof is present, then the weight ratio of the compound of formula (I) to pyriminobac-methyl is from 180:12 to 10:175, or from 150:12 to 10:175; if pyribenzoxim or a salt thereof is present, then the weight ratio of the compound of formula (I) to pyribenzoxim is from 180:10 to 10:70, or from 150:10 to 10:70; and if penoxsulam or a salt thereof is present, then the weight ratio of the compound of formula (I) to penoxsulam is from 180:2 to 10:60, or from 150:2 to 10:60.
2. 2. A herbicidal composition as claimed in claim 1, wherein, in the compound of formula (I): R1 is methyl, ethyl, cyclopropyl, chlorine, difluoromethoxy or trifluoromethoxy; and R2 is 4-chlorophenyl, 2,4-dichlorophenyl, 4-chloro-2-fluorophenyl, 4-chloro-2-methylphenyl, 4-chloro-2-difluoromethylphenyl, 4-chloro-2-methoxyphenyl, 4-chloro-2-cyanophenyl, 3,4-dichlorophenyl, 4-chloro-3-methoxyphenyl, 4-chloro-3-cyanophenyl, 4-chloro-2-fluoro-3-trifluoromethylphenyl, or 4-chloro-2,6-difluorophenyl; and R5 and R6, independently of each other, are hydrogen or methyl; and R4 and R7, independently of each other, are hydrogen, methyl, ethyl or methoxymethyl; provided that at least one of R4, R5, R6 and R7 is or are not hydrogen; and G is hydrogen, -C(O)-C1-C4alkyl or -C(O)-O-C1-C4alkyl.
3. 3. A herbicidal composition as claimed in claim 1 or 2, wherein the compound of formula (I) or the agriculturally acceptable salt thereof comprises: one of the following compounds: A-4, D-7, D-8, D-12, D-13, D-15, D-16, D-18, D-21, A-45 (also named Compound no. 1), 0-23, D-26 (also named Compound no. 5), AA-13 (also named Compound no. 2), AA-14, AA-15, A-66 (also named Compound no. 3), AA-5, AA-6, AA-12 (also named Compound no. 4), A-167, A-5, A-49, A-Si, A-59, A-70, A-34, A-35, A-26, A-fl, A-64, A-65, A-67, A-69, A-79, A-99, A-100, A-101, A-141, A-142, A-149, A-144, A-154, A-155, A-158, 8.007, 8.049, 8.056, 14.055, 14.056, 14.058, 14.059, 14.060, 14.073, 17.035, 17.059, 17.065, 17.066, 17.071, 17.074, 17.084, 18.049, 18.058, 18.060, 20.049, 20.052, 20.055, 20.056, 20.058, 20.059 0120.060, whose structures are shown below; or an agriculturally acceptable salt thereof: _:,jji1IEJII:I'1%iIII:;L I ±iII1IIIIIL1 (A-4) (D-7) (D-8) FOcI (D-12) (0-13) (D-15) -16) ci (0-18) (D-21) _ 0 0 0 > Os 0 0 /\ >(>=o& 0 0 /B r\/-1 aO aO / / o aB a MB m -pfl) oW / C, 0B -(p-a -a a a p p p p ->K/° /0 rj a -x 0-> > o-o o-o 01 a) -x-P P P P P / / 0-> >Ko 0 /\00 00 o 00 2a / 0 0 >( )_o a0 ft rn 0 0 0 o 0 0 0 0 0 0 0 0 >oy >oc >oc oc 0c ::: 0 0 0 0 0 0 0 0 o o o o o 01=0I I H H-F F / )( )=o)( )=o)( )=o --C)I mm 90I I H-H- o-%5' o Th >( >=o)( )=o --(_) I001I HI IIcI(20.060)
4. 4. A herbicidal composition as claimed in claim 3, wherein the compound of formula (I) or the agriculturally acceptable salt thereof comprises: one of the following compounds: A-4, D-7, D-8, D-12, D-13, D-15, D-16, D-18, D-21, A-45 (also named Compound no. 1), 0-23, D-26 (also named Compound no. 5), AA-13 (also named Compound no. 2), AA-14, AA-15, A-66 (also named Compound no. 3), AA-5, AA-6, AA-12 (also named Compound no. 4), A-167, A-5, A-49, A-Si, A-59, A-70, A-26, A-64, A-65, A-69, A-99, A-14i, A-i42, A-154, A-i58, 14.059, 17.066, 17.071, 17.074, 18.049, 20.049, 20.052, 20.055, 20.056, 20.058, 20.059 or 20.060, whose structures are shown in claim 3; or an agriculturally acceptable salt thereof.
5. 5. A herbicidal composition as claimed in claim i, 2, 3 or 4, wherein the compound of iS formula (I) or the agriculturally acceptable salt thereof is a compound of formula (IA) or a compound of formula (IS) or an agriculturally acceptable salt of either of these: (IA) (IB), wherein, in formula (IA), R1 is ethyl or cyclopropyl, and R2A is hydrogen, chlorine or fluorine.
6. 6. A herbicidal composition as claimed in claim 5, wherein, in formula (IA), R2A is chlorine or fluorine.
7. 7. A herbicidal composition as claimed in claim 6, wherein, in the compound of formula (IA) or the salt thereof, S1 is ethyl.
8. 8. A herbicidal composition as claimed in claim 7, wherein, in the compound of formula (IA) or the salt thereof, 1 is ethyl and 5M is chlorine.
9. 9. A herbicidal composition as claimed in claim 1, 2, 3, 4, 5, 6, 7 orB, wherein the compound of formula (I) or (IA) or the salt thereof is present as the compound.
10. 10. A herbicidal composition as claimed in claim 6, wherein, in the compound of formula (IA) or the salt thereof, l is cyclopropyl.
11. 11. A herbicidal composition as claimed in claim 10, wherein, in the compound of formula (IA) or the salt thereof, l is cyclopropyl and 52A is fluorine.
12. 12. A herbicidal composition as claimed in claim 10 or 11, wherein the compound of formula (I) or (IA) or the salt thereof is present as the compound.
13. 13. A method of controlling weeds in crops of useful plants, which comprises applying a herbicidal composition, as defined in any one of claims ito 12, to the weeds and/or to the useful plants and/or to the locus thereof
14. 14. A method as claimed in claim 13, wherein the compound of formula (I) or the agriculturally acceptable salt thereof is as defined in claim 2, 3 or 4.
15. 15. A method as claimed in claim 13, wherein the compound of formula (I) or the agriculturally acceptable salt thereof is a compound of formula (IA) or the agriculturally acceptable salt thereof, wherein either l is ethyl and R2A is chlorine, or R1 is cyclopropyl and R2A is fluorine.
16. 16. A method as claimed in claim 13, 14 or 15, wherein the weeds and/or the useful plants and/or the locus thereof are flooded.
17. 17. A method as claimed in claim 16, which comprises applying the herbicidal composition to the flooded locus of the flooded weeds and/or the flooded useful plants.
18. 18. A method as claimed in claim 17, which comprises applying the herbicidal composition to the flood-waters at the flooded locus of the flooded weeds and/or the flooded useful plants.
19. 19. A method as claimed in claim 13, 14, 15, 16, 17 or 18, , wherein the herbicidal composition is applied post-emergence.
20. 20. A method as claimed in claim 13, 14, 15, 16, 17, 18 or 19, wherein the crops of useful plants are rice.
21. 21. A method as claimed in claim 20, wherein the rice is direct-seeded rice.
22. 22. A method as claimed in claim 13, 14, 15, 16, 19,20 or 21, wherein the herbicidal composition is applied post-emergence by foliar and/or spray application.
23. 23. A method as claimed in claim 21 or 22, wherein the application rate for the compound of formula (I) or the agriculturally acceptable salt thereof, is from 30 to 150 g/ha of the compound of formula (I) or the salt thereof, calculated as the free compound.
24. 24. A method as claimed in claim 13, 14, 15, 16, 17, 18 or 19, wherein the crops of useful plants are transplanted flooded rice.
25. 25. A method as claimed in claim 24, wherein the herbicidal composition is applied to the flood-waters of the transplanted flooded rice at an application rate, for the compound of formula (I) or the salt thereof, of from 30 to 250 g/ha of the compound of formula (I) or a salt thereof, calculated as the free compound.
26. 26. A method as claimed in claim 25, wherein the herbicidal composition is applied to the flood-waters of the transplanted flooded rice at an application rate, for the compound of formula (I) or the salt thereof, of from 50 to 180 g/ha of the compound of formula (I) or a salt thereof, calculated as the free compound.-121 -
27. 27. A method as claimed in any of claims 13 to 26, wherein the weeds to be controlled comprise: Echinochloa, Brachiaria, Leptochloa, Scirpus, Monochoria, Fimbristylis, and/or Cyperus.
28. 28. A method as claimed in any of claims 13 to 26, wherein the weeds to be controlled comprise Echinochloa and/or Brachiaria and/or Leptochloa.
29. 29. A herbicidal composition comprising: (a) a compound of formula (I) or an agriculturally acceptable salt thereof: R R (I), wherein the substituents within the compound of formula (I), and/or the compound of formula (I) or the salt thereof, are as defined in any of claims ito 12; and (b) an ALS (acetolactate synthase) inhibitor herbicide suitable for use on rice, wherein the rice-suitable ALS inhibitor herbicide is bensulfuron-methyl, pyrazosulfuron-ethyl, azimsulfuron, flucetosulfuron, orthosulfamuron, prosulfuron, triasulfuron, trifloxysulfuron, bispyribac, pyriminobac-methyl, pyribenzoxim, and/or penoxsulam, or an agriculturally acceptable salt of any of these; and (c) a safener which is a compound of the following formula: Me O1+O 0 0 or an agriculturally acceptable salt thereof or which is cyprosulfamide or an agriculturally acceptable salt thereof.-122-
30. 30. A herbicidal composition as claimed in claim 29, wherein the compound of formula (I) is a compound of formula (IA) or a compound of formula (IB), or an agriculturally acceptable salt thereof: R2A Cl (IA) HCI (IB), wherein, in formula (IA), R1 is ethyl or cyclopropyl, and R2A is chlorine or fluorine.