GB2282537A - Herbicidal compositions containing ketones derived from monic acid - Google Patents

Abstract

A herbicidal composition comprising a compound of formula (I) in admixture with a herbicidally acceptable carrier or diluent <IMAGE> wherin R<1> is an alkyl, alkenyl, alkynyl, alkylcycloalkyl, aryl, aralkyl or heterocyclyl group, each of which group is optionally substituted.

Description

HERBICIDAL COMPOSITIONS This invention relates to herbicidal compositions and processes utilising them.

A number of derivatives of monic acid are known to have utility as biologically active compounds for use in human and veterinary medicine.

Such compounds are described inter alia in International application WO 92/02518, European patent application 0,029,665, International application WO 93/15072, International application WO 91/09855, and J. Med.

Chem., 1989, 32, 151, the disclosure of which is incorporated by reference.

We have now found that compounds such as those disclosed in the above references have herbicidal activity.

Thus according to the present invention there is provided a herbicial composition comprising a compound of formula (I) in admixture with a herbicidally acceptable carrier or diluent , wherein R1 is an optionally substituted alkyl, optionally substituted alkylcycloalkyl, optionally substituted aryl, optionally substituted aralkyl or optionally substituted heterocyclyl group.

Optionally substituted C1 10 alkyl groups, optionally substituted C37 cycloalkyl groups, optionally substituted C2-10 alkenyl groups and optionally substituted C2~ alkyl groups are preferred.Optional substituents which may be present in optionally substituted alkyl, alkenyl or alkynyl groups include C37 cycloalkyl, C11O alkoxy, C1 lO alkylthio, C28 alkenyloxy, C28 alkenylthio, C28 alkynyloxy, C28 alkynylthio, halogen, halo-C1-10 alkoxy, halo2 8 alkenyloxy, halo2 8 alkynyloxy, carboxy, C16 alkoxycarbonyl, carbamoyl, aryl (which may itself be optionally substituted), aryloxy (which may itself be optionally substituted), aralkyl (which may itself be optionally substituted), aralkyloxy (which may itself be optionally substituted), heterocyclyl (which may itself be optionally substituted), heterocyclyloxy (which may itself be optionally substituted), hydroxy, cyano, nitro, C16 alkanoyloxy, amino, mono- and di- (C1-6) alkylamino.

The terms alkyl, alkylcycloalkyl, alkenyl and alkynyl also include those alkyl, alkylcycloalkyl, alkenyl and alkynyl groups disclosed in EP 0,029,665 and suitable substituents for alkyl, alkenyl and alkynyl include those substituents disclosed therein, which alkyl, alkenyl and alkynyl groups and substituents are incorporated herein by reference as are individual compounds disclosed in EP 0,029,665.

The term "aryl" as used herein includes phenyl and naphthyl each of which may be optionally substituted with up to five substituents independently selected from halogen, C16 alkyl, C16 alkoxy, C16 alkylthio, halo-(C1 6) alkyl, hydroxy-(C1 6) alkyl, halo-(C1 ) alkoxy, C28 alkenyl, C28 alkenyloxy, C28 alkenylthio, C28 alkynyl, C28 alkynyloxy, C28 alkynylthio, hydroxy, cyano, nitro, amino, mono- and di (C1-6) alkylamino, C16 alkanesulphinyl, C1 6 alkanesulphonyl, carboxy, C1 6 alkoxycarbonyl, C16 alkoxycarbonyl(C16)alkyl, methylenedioxy, aryl (which may itself be substituted), aryloxy (which may itself be substituted), C14 aralkyloxy (which may itself be substituted), or heterocyclyl or heterocyclyloxy (which may itself be substituted). The term aryl also includes those aryl groups disclosed in WO 91/09855 and EP 0,029,665 and suitable substituents for aryl include those substituents for aryl disclosed therein, which aryl groups and substituents are incorporated herein by reference as are individual compounds disclosed in WO 91/09855 and EP 0,029,665.

The term aralkyl as used herein includes groups in which the aryl moiety is a phenyl group which may be optionally substituted as hereinbefore defined for aryl and in which the alkylene radical has from 1 to 4 carbon atoms. A preferred aralkyl group is optionally substituted benzyl. The term aralkyl also includes those aralkyl groups disclosed in EP 0,029,665 and suitable substituents for aralkyl include those substituents for aralkyl disclosed therein, which aralkyl groups and substituents are incorporated herein by reference as are individual compounds disclosed in EP 0,029,665.

The term "heterocyclyl" as used herein includes aliphatic or aromatic single or fused rings each ring containing a total of from 3 to 8 ring atoms and containing up to four hetero atoms in the ring selected from oxygen, nitrogen and sulphur and optionally substituted with aryl (which may itself be substituted), with another heterocyclic ring (which may itself be substituted) or with one or more of those substituents mentioned above as optional substituents for aryl.Examples of suitable heterocyclyl rings for use in the present invention include furyl, thienyl, pyrrolyl, benzofuranyl, benzthienyl, indolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, benzimidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, thiatriazolyl, pyridyl (such as pyrid-3-yl and pyrid-4-yl), quinolinyl, isoquinolinyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl. The term heterocyclyl also includes those heterocyclyl groups disclosed in EP 0,029,665, W0/92 02581 and WO 93/15072 and suitable substituents for heterocyclyl include those substituents for heterocyclyl disclosed therein, which heterocyclyl groups and substituents are incorporated herein by reference, as are individual compounds disclosed in EP 0,029,665, WO 92/02518 and WO 93/15072.

Examples of preferred compounds for use in the present invention include those in which R1 is optionally substituted C1 10 alkyl, optionally substituted aryl, particularly phenyl, and optionally substituted heterocyclyl, particularly thienyl and thiazolyl.

Preferred substituents for the alkyl, aryl and heterocyclyl groups include alkoxy, alkylthio and halo, particularly chloro or bromo.

Particularly suitable compounds are listed in Table 1.

Examples of suitable compounds for use in compositions of the present invention are listed in Table 1.

TABLE 1 Compound R1 Number 1 CH CH2CH2-OC2H5 2 n-butyl 3 4-chlorophenyl 4 2-thienyl 5 2-(2-Methoxyethoxy)thiazol-5-yl Compounds for use in the present invention are either known compounds or may be prepared by methods analogous to those used for the preparation of correspono.,lg known compounds. Several suitable methods of preparation of the compounds for use in the composition of the present invention are described in the literature.

One route for the preparation of the compounds of formula (I) uses as a starting material the protected aside (6) which is shown in Scheme 1 and which can be prepared according to the method described in WO 93/06118.

This amide is reacted with a Grignard reagent of formula: RlMgBr where R1 is as defined above and subsequently deprotected using dilute acid.

An alternative method for the preparation of the compounds of formula (I) is to react a protected aldehyde of formula (7) shown in Scheme 2 with an organolithium reagent of formula R1Li which can be prepared by methods well known to those skilled in the art.

The resulting protected alcohol may be reacted with an oxidising agent such as manganese dioxide to form the corresponding protected ketone which may be deprotected, again using methods known in the art such as treatment with dilute acid. The preparation of the starting material, aldehyde (7) is described in WO 92/02518.

The compounds for use in the compositions of the present invention are active against a broad range of weed species including monocotyledonous and dicotyledonous species. Many compounds show good selectivity in crops, particularly wheat, barley, maize, oil seed rape, sugar beet and rice. The compounds for use in compositions of the present invention are preferably applied directly to unwanted plants (post-emergence application) but they may also be applied to the soil before the unwanted plants emerge (pre-emergence application).

Thus according to a further aspect of the present invention there is provided a process of severely damaging or killing unwanted plants, which comprises applying to the plants or the the growth medium of the plants a herbicidally effective amount of a compound of the formula (I) as hereinbefore defined wherein R1 is as hereinbefore defined.

Novel compounds of the present invention are preferably used in the form of a composition comprising a compound of formula (I) in admixture with a carrier comprising a solid or liquid diluent.

Suitable compositions of the present inv .it-i-on include both dilute compositions, which are ready for immediate use, and concentrated compositions, which require to be diluted before use, usually with water.

Preferably the compositions contain from 0.01% to 90% by weight of the active ingredient. Dilute compositions ready for use preferably contain from 0.01 to 2% of active ingredient, while concentrated compositions may contain from 20 to 90% of active ingredient, although from 20 to 70% is usually preferred.

The solid compositions may be in the form of granules, or dusting powders wherein the active ingredient is mixed with a finely divided solid diluent, e.g. kaolin, bentonite, kieselguhr, dolomite, calcium carbonate, talc, powdered magnesia, Fuller's earth and gypsum. They may also be in the form of dispersible powders or grains, comprising a wetting agent to facilitate the dispersion of the powder or grains in liquid. Solid compositions in the form of a powder may be applied as foliar dusts.

Liquid compositions may comprise a solution or dispersion of an active ingredient in water optionally containing a surface-active agent, or may comprise a solution or dispersion of an active ingredient in a water-immiscible organic solvent which is dispersed as droplets in water.

Surface-active agents may be of the cationic, anionic, or non-ionic type or mixtures thereof. The cationic agents are, for example, quaternary ammonium compounds (e.g. cetyltrimethylammonium bromide). Suitable anionic agents are soaps; salts of aliphatic mono ester of sulphuric acid, for example sodium lauryl sulphate; and salts of sulphonated aromatic compounds, for example sodium dodecylbenzenesulphonate, sodium,calcium, and ammonium lignosulphonate, butylnaphthalene sulphonate, and a mixture of the sodium salts of diisopropyl and triisopropylnaphthalenesulphonic acid.

Suitable non-ionic agents are the condensation products of ethylene oxide with fatty alcohols such as oleyl alcohol and cetyl alcohol, or with alkylphenols such as octyl- or nonyl- phenol (e.g. Agral 90) or octyl-cresol. Other non-ionic agents are the partial esters derived from long chain fatty acids and hexitol anhydrides, for example sorbitan monolaurate; the condensation products of the partial ester with ethylene oxide; the lecithins; and silicone surface active agents (water soluble surface active agents having a skeleton which comprises a siloxane chain e.g. Silwet L77). A suitable mixture in mineral oil is Atplus 411F.

The aqueous solutions or dispersions may be prepared by dissolving the active ingredient in water or an organic solvent optionally containing wetting or dispersing agent(s) and then, when organic solvents are used, adding the mixture so obtained to water optionally containing wetting or dispersing agent(s). Suitable organic solvents include, for example, ethylene dichloride, isopropyl alcohol, propylene glycol, diacetone alcohol, toluene, kerosene, methyinaphthalene, the xylenes and trichloroethylene.

The compositions for use in the form of aqueous solutions or dispersions are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, and the concentrate is then diluted with water before use. The concentrates are usually required to withstand storage for prolonged periods and after such storage, to be capable of dilution with water to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment. Concentrates conveniently contain 20-90%, preferably 20-70%, by weight of the active ingredient(s). Dilute preparations ready for use may contain varying amounts of the active ingredient(s) depending upon the intended purpose; amounts of 0.01% to 10.0% and preferably 0.1% to 2%, by weight of active ingredient(s) are normally used.

A preferred form of concentrated composition comprises the active ingredient which has been finely divided and which has been dispersed in water in the presence of a surface-active agent and a suspending agent.

Suitable suspending agents are hydrophilic colloids and include, for example, polyvinylpyrrolidone and sodium carboxymethylcellulose, and the vegetable gums, for example gum acacia and gum tragacanth. Preferred suspending agents are those which impart thixotropic properties to, and increase the viscosity of the concentrate. Examples of preferred suspending agents include hydrated colloidal mineral silicates, such as montmorillonite, beidellite, nontronite, hectorite, saponite, and saucorite. Bentonite is especially preferred. Other suspending agents include cellulose derivatives and polyvinyl alcohol.

The rate of application of the compounds of the invention will depend on a number of factors including, for example, the compound chosen for use, the identity of the plants whose growth is to be inhibited, the formulations selected for use and whether +e compound is to be applied for foliage or root uptake. As a general guide, however, an application rate of from 0.0001 to 20 kilograms per hectare is suitable while from 0.001 to 10, for example 0.001 to 2 kilograms per hectare may be preferred.

The compositions of the invention may comprise, in addition to one or more compounds of the invention, one or more compounds not of the invention but which possess biological activity. Accordingly in yet a still further embodiment the invention provides a herbicidal composition comprising a mixture of at least one herbicidal compound of formula (I) as hereinbefore defined with at least one other herbicide.

The other herbicide may be any herbicide not having the formula (I).

It will generally be a herbicide having a complementary action in the particular application.

Examples of useful complementary herbicides include: A. benzo-2,1,3-thiadiazin-4-one-2,2-dioxides such as bentazone; B. hormone herbicides, particularly the phenoxy alkanoic acids such as MCPA, MCPA-thioethyl, dichlorprop, 2,4,5-T, MCPB, 2,4-D, 2,4-DB, mecoprop, trichlopyr, clopyralid, and their derivatives (eg. salts, esters and amides); C. 1,3 dimethylpyrazole derivatives such as pyrazoxyfen, pyrazolate and benzofenap; D.Dinitrophenols and their derivatives (eg. acetates) such as dinoterb, dinoseb and its ester, dinoseb acetate; E. dinitroaniline herbicides such as dinitramine, trifluralin, ethalflurolin, pendimethalin, oryzalin; ** F. arylurea herbicides such as diuron , flumeturon, metoxuron, neburon, ** ** isoproturon , chlorotoluron , chloroxuron, linuron, monolinuron, chlorobromuron, daimuron, methabenzthiazuron; G. phenylcarbamoyloxyphenylcarbamates such as phenmedipham and desmedipham; H. 2-phenylpyridazin-3-ones such as chloridazon and norflurazon; ** I. uracil herbicides such as lenacil , bromacil and terbacil; ** J. triazine herbicides such as atrazine , simazine, aziprotryne, cyanazine, prometryn, dimethametryn, simetryne, and terbutryn; K. phosphorothioate herbicides such as piperophos, bensulide, and butamifos;; L. thiocarbamate herbicides such as cycloate, vernolate, molinate, * * thiobencarb, butylate , EPTC , tri-allate, di-allate, esprocarb, ** tiocarbazil, pyridate, prosulfocarb and dimepiperate; M. 1,2,4-triazin-5-one herbicides such as metamitron and metribuzin; N. benzoic acid herbicides such as 2,3,6-TBA, dicamba and chloramben; 0. anilide herbicides such as pretilachlor, butachlor, alachlor, ** propachlor, propanil, metazachlor, metolachlor, acetochlor , and dimethachl or; ** P. dihalobenzonitrile herbicides such as dichlobenil, bromoxynil and ioxynil; Q. haloalkanoic herbicides such as dalapon, TCA and salts thereof;; R. diphenylether herbicides such as lactofen, fluroglycofen or salts or ester thereof, nitrofen, bifenox, aciflurofen and salts and esters thereof, oxyfluorfen, fomesafen, chlornitrofen and chlomethoxyfen; S. phenoxyphenoxypropionate herbicides such as diclofop and esters ** thereof such as the methyl ester, fluazifop and esters thereof, haloxyfop and esters thereof, quizalofop and esters thereof and fenoxaprop and esters thereof such as the ethyl ester; T. cyclohexanedione herbicides such as alloxydim and salts thereof, sethoxydim, cycloxydim, tralkoxydim , and clethodim; U. sulfonyl urea herbicides such as chlorsulfuron, sulfometuron, metsulfuron and esters thereof; benzsulfuron and esters thereof such as DPX-M6313, chlorimuron and esters such as the ethyl ester thereof pirimisulfuron and esters such as the methyl ester thereof, 2-t3-(4-methoxy-6-methyl-1,3,5- triazin-zyl)-3-methylureidosulphonyl) benzoic acid esters such as the methyl ester thereof (DPX-LS300) and pyrazosul furon; V. imidazolidinone herbicides such as imazaquin, imazamethabenz, imazapyr and isopropylammonium salts thereof, imazethapyr; W. arylanilide herbicides such as flamprop and esters thereof, ** benzoylprop-ethyl, diflufenican ; X. amino acid herbicides such as glyphosate and glufosinate and their ** ** salts and esters , sulphosate (glyphosate trimesium) and bialaphos; Y. organoarsenical herbicides such as monosodium methanearsonate (MSMA);; . herbicidal amide derivative such as napropamide, propyzamide, carbetamide, tebutam, bromobutide, isoxaben, naproanilide and naptalam; AA triketones such - sulcotrione; BB. miscellaneous herbicides including ethofumesate, cinmethylin, difenzoquat and salts thereof such as the methyl sulphate salt, clomazone, oxadiazon, bromofenoxim, barban, tridiphane, flurochloridone, quinchlorac and mefanacet; CC. Examples of useful contact herbicides include: bipyridylium herbicides such as those in which the active entity is paraquat and those in which the active entity is diquat; * These compounds are preferably employed in combination with a safener such as dichlormid.

** These compounds have been demonstrated to exhibit additive and in several instances synergystic effects when applied in admixture with compounds of the present invention.

It is an advantage of preferred compounds of the present invention that they are compatible with a wide range of co-herbicides such as those listed above and may exhibit additive or synergystic effects in such mixtures.

The invention will now be further described with reference to the following examples.

EXAMPLE 1 Preparation of Compound 1 of Table 1.

Compound 1 was prepared from the amide (6) according to the route shown in Scheme 1.

A Grignard reagent was prepared from 1-bromo-3-ethoxypropane (1.0g, 5.99mmol) and magnesium turnings (0.159, 6.17mmol) in dry tetrahydrofuran (THF, 10 ml) under an atmosphere of nitrogen. Part of the resulting solution (2.1 ml, ca. 1.2 mmol of the Grignard reagent) was added dropwise to a stirred solution of the amide (6) (500 mg, 0.83 mmol, prepared as described in WO 93/06118, SmithKline Beecham) in dry THF (6 ml) and under an atmosphere of nitrogen at -100C. Following the addition, the reaction mixture was stirred at -10 C for 15 minutes, then allowed to warm to room temperature and stand overnight (ca. 16 hours). Saturated aqueous ammonium chloride (2 m:; and water (20 ml) were then added successively to the reaction mixture with vigorous stirring, and the mixture was then extracted with dimethyl ether. The extracts were washed with brine, dried over magnesium sulphate and concentrated under reduced pressure to give a colourless oil. This oil was dissolved in THF (10 ml) and 0.4 M hydrochloric acid (2 ml) was added in one portion. The mixture was stirred for 2.5 minutes, then saturated aqueous sodium hydrogen carbonate solution (20 ml) was added and the resulting mixture was extracted with ethyl acetate. The extracts were washed with brine, dried over magnesium sulphate and concentrated under reduced pressure to give a pale yellow oil.

Purification by column chromatography on silica gel using 7% methanol in tbutyl methyl ether as eluent then gave the title Compound 1 as a viscous pale yellow oil (200 mg, 58% yield overall). The proton NMR data are set out in Table 2.

EXAMPLES 2 to 4 Preparation of Compounds 2-4 of Table 1.

Compounds 2 to 4 were prepared from the amide (6) and an appropriate Grignard reagent using a method analagous to that described in Example 1.

Again, the NMR data are set out in Table 2.

EXAMPLE 5 Preparation of Compound 5.

Compound 5 of Table 1 was prepared from the aldehyde (7) using the route shown in Scheme 2.

n-Butyl-lithium (0.53 ml of a 2.25 M solution in hexanes, 1.19 mmol) was added dropwise over 5 minutes to a solution of 2-(2methoxyethoxy)thiazole (0.19 g, 1.19 mmol, prepared as described in WO 93/15072, in dry THF (5 ml) and under an atmosphere of dry nitrogen at 700C. The resulting mixture was allowed to stir at -700C for 30 minutes, then a solution of the aldehyde (7) (0.59 g, 1.08 mmol, prepared as described in WO 92/02518, SmithKline Beecham) in dry THF (5 ml) was added dropwise over 5 minutes. After a further hour at -700C, saturated aqueous ammonium chloride solution (2.0 ml) was added in one portion and the mixture was allowed to warm to room temperature. Water was then added, and it was extracted with ether.The extracts were washed with saturated brine, then dried over magnesium sulphate and concentrated under reduced pressure to give a colourless oil. Column chromatography on silica gel using a mixture of t-butyl methyl ether and hexane (3:1) as eluent gave the alcohol (8) as a mixture of diastereomers, a colourless oil (460 mg).

A mixture of the alcohol (8) (453 mg, 0.64 mmol), activated manganese dioxide (226 mg, 2.60 mmol) and powdered 4-angstrom molecular sieve (1.0 g) in dichloromethane (12 ml) was stirred at room temperature. Further portions of manganese dioxide (200 mg) were added after 5 hours and 21 hours. Finally, after a total of 25 hours from the start of the reaction, the mixture was applied to the top of a column of silica gel made up with a 1:1 mixture of t-butyl methyl ether and hexane, and it was eluted with the same solvent mixture to give the silylated ketone (9).

The ketone (9) was desilylated with 0.4 M hydrochloric acid in the way described in example 1. The crude product, a viscous oil, was purified by column chromatography on silica gel using increasing proportions (3 to 10%) of methanol in t-butyl methyl ether as eluent to give the title compound, Compound 5, as a colourless foam which could be broken up into an amorphous solid (170 mg), with proton NMR data as in Table 2.

Table 2: Proton NMR data for the compounds of Table 1. All data were recorded on an instrument operating at 270 MHz, with CDCl3 as solvent and tetramethylsilane as internal standard. The signals listed below are representative only: the complete spectrum is not recorded for each compound. Key: s = singlet, d = doublet, t = triplet, m = multiplet.

Compound 1 3 0.94(3H,d), 1.18(3H,t), 1.22(3H,d), 2.18(3H,s), 3.44 (4H,m), 6.16(1H,s)ppm.

Compound 2 8 0.92(6H,m), 1.22(3H,d), 2.18(3H,s), 2.44(2H,t), 6.14 (1H,s)ppm.

Compound 3 3 0.96(3H,d), 1.22(3H,d), 2.23(3H,s), 6.77(1H,s), 7.42 (2H,d), 7.87(2H,d)ppm.

Compound 4 8 0.94(3H,d), 1.22(3H,d), 2.28(3H,s), 6.76(1H,s), 7.11 (1H, t), 7.60(1H,d), 7.70(1H,d)ppm.

Compound 5 3 0.94(3H,d), 1.22(3H,d), 2.25(3H,s), 3.43(3H,s), 3.75 (2H,m), 4.62(2H,m), 6.60(1H,s), 7.73(1H,s) ppm.

EXAMPLE 6 This Example illustrates the herbicidal properties of compounds according to the invention.

The herbicidal activity f the compounds was tested as follows: Each chemical was formulated by dissolving it in an appropriate amount, dependent on the final spray volume, of a solvent/surfactant blend which comprised 78.2 gm/litre of Tween 20 and 21.8 gm/litre of Span 80 adjusted to 1 litre using methylcyclohexanone. Tween 20 is a Trade Mark for a surface-active agent comprising a condensate of 20 molar proportions of ethylene oxide with sorbitan laurate. Span 80 is a Trade Mark for a surface-active agent comprising sorbitan mono-laurate. If the chemical did not dissolve, the volume was made up to 5cm3 with water, glass beads were added and this mixture was then shaken to effect dissolution or suspension of the chemical, after which the beads were removed. In all cases, the mixture was then diluted with water to the required spray volume.If sprayed independently, volumes of 25cm3 and 30cm3 were required for pre-emergence and post-emergence tests respectively; if sprayed together, 45cm3 was required. The sprayed aqueous emulsion contained 4% of the initial solvent/surfactant mix and the test chemical at an appropriate concentration.

The spray compositions so prepared were sprayed onto young pot plants (post-emergence test) at a spray volume equivalent to 400 litres per hectare. Damage to plants was assessed 13 days after spraying by comparison with untreated plants, on a scale of O to 9 where 0 is 0% damage, 1 is 1-5% damage, 2 is 6-15% damage, 3 is 16-25% damage, 4 is 26-35% damage, 5 is 36-59% damage, 6 is 60-69% damage, 7 is 70-79% damage, 8 is 80-89% damage and 9 is 90-100% damage.

The designation "-" indicates that a compound was not tested against the indicated species.

The results of the tests are given in Table 3 below in which the rate of application was 500 g/ha.

Table 3 Test Plant Comp'd BN GM ZM OS TA PA MI CA GA AR PO IH AT XT AF AM LR SH SV BP PD EC CE 1 -8122999498979522688264 2 34110879598521100095270 3 -5221999759544522534534 4 -4200227465724010344522 5 -3322427595914530354232 TABLE 4 Abbreviations used for Test Plants BN - Rape GM - Soybean ZM - Maize OS - Rice TA - Winter wheat PA - Polvaonum aviculare CA - Chenopodium album GA - Galium aparine AR - Amaranthus retroflexus PO - Portulaca oleracea IH - Ipomoea hederacea (post-emergence) AT - Abutilon theophrasti XT - Xanthium strumarium AF - Avena fatua AM - Alopecurus myosuroides 'R - Lolium ripidum SH - Sorghum halepense SV - Setaria viridis BP - Brachiaria platyphylla EC - Echinochloa crus-aalli CE - Cyperus esculentus MI - Matricaria perforata LR - Lolium rigidum Pp - Panicuum dicotomifirum CHEMICAL FORMULA (as in description)

SCHEME 1

SCHEME 2

Claims (8)

1. CLAIMS 1. A herbicidal composition comprising a compound of formula (I) in admixture with a herbicidally acceptable carrier or diluent

   wherein R1 is an optionally substituted alkyl, optionally substituted alkylcycloalkyl, optionally substituted aryl optionally substituted aralkyl or optionally substituted heterocyclyl group.
2. 2. A composition as claimed in claim 1, wherein R1 is C1-10 alkyl, C3-7 cycloalkyl, C2 10 alkenyl or C210 alkynyl, any of which may optionally be substituted with C3 7 cycloalkyl, C1 10 alkoxy, C1 10 alkylthio, C2-8 alkenyloxy, C2-8 alkenylthio, C2-8 alkynyloxy, C2~8 alkynylthio, halogen, halo-1-10 alkoxy, halo, alkenyloxy, halo-C2-8 alkynyloxy, carboxy, C1-6 alkoxycarbonyl, carbamoyl, aryl (which may itself be optionally substituted), aryloxy (which may itself be optionally substituted), aralkyl (which may itself be optionally substituted), aralkyloxy (which may itself be optionally substituted), heterocyclyl (which may itself be optionally substituted), heterocyclyloxy (which may itself be optionally substituted), hydroxy, cyano, nitro, C1-6 alkanoyloxy, amino, mono and di-(C1-6) alkylamino; or R1 is aryl, optionally substituted with up to five substituents independently selected from halogen, C1-6 alkyl, 1-6 alkoxy, C1 6 alkylthio, halo-(C1 6) alkyl, hydroxy-(C1 6) aikyl, halo-(C. 6) alkoxy, C2-8 alkenyl, C2-8 alkenyloxy, C2-8 alkenylthio, C28 alkynyl, C2-8 alkynyloxy, C2-8 alkynylthio, hydroxy, cyano, nitro, amino, mono- and di- (C. 6) alkylamino, C1-6 alkanesulohinyl, C1 6 alkanesulphonyl, carboxy, C1-6 alkoxycarbonyl, C16 alkoxycarbonyl(C16)alkyl, methylenedioxy, aryl (which may itself be substituted), aryloxy (which may itself be substituted), C14 aralkyloxy (which may itself be substituted), or heterocyclyl or heterocyclyloxy (which may itself be substituted).
3. 3. A composition as claimed in claim 2, wherein R1 is optionally substituted C1 10 alkyl, optionally substituted aryl or optionally substituted heterocyclyl.
4. 4. A composition as claimed in claim 3, wherein R1 is optionally substituted C1-10 alkyl, optionally substituted phenyl or optionally substituted thienyl or thiazolyl.
5. 5. A composition as claimed in claim 3 or claim 4, wherein the alkyl, aryl or heterocyclyl groups are substituted with alkoxy, alkylthio or halo.
6. 6. A composition as claimed in any one of claims 1 to 5, comprising a compound of formula (I) as defined above in which R1 is 3-ethoxy propyl, n-butyl, 4-chlorophenyl, 2-thienyl or 2- (2-methoxyethoxy) thi azol -5-yl.
7. 7. A composition as claimed in any one of claims 1 to 6 which further contains a complementary herbicide.
8. 8. A process for severely damaging or killing unwanted plants, the process comprising applying to the plants a herbicidally effective amount of a compound of formula (I) as defined in claim 1.