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GB2223946A - Herbicidal compositions and their use - Google Patents

Herbicidal compositions and their use Download PDF

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Publication number
GB2223946A
GB2223946A GB8824836A GB8824836A GB2223946A GB 2223946 A GB2223946 A GB 2223946A GB 8824836 A GB8824836 A GB 8824836A GB 8824836 A GB8824836 A GB 8824836A GB 2223946 A GB2223946 A GB 2223946A
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alkyl
herbicidal composition
haloalkyl
optionally substituted
formula
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GB8824836D0 (en
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Michael Derek Barker
Mark Vincent Smith
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SHELL INT RESEARCH
Shell Internationale Research Maatschappij BV
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SHELL INT RESEARCH
Shell Internationale Research Maatschappij BV
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

A herbicidal composition comprising as active ingredient at least one indeno-[1,2-c]-pyrazol-4-one derivative of formula (I): <IMAGE> wherein R1 is an acyl group, R2 is an optionally substituted alkyl or cycloalkyl group and X represents halogen, nitro, alkyl, haloalkyl, alkoxy or haloalkoxy, and n is 0, 1 or 2, is useful for preventing or combating undesired plant growth at a locus.

Description

HERBICIDAL COMPOSITIONS AND THEIR USEw The present invention relates to a herbicidal composition and to its use in preventing or controlling undesired plant growth.
3-Substituted and 1,3-disubstituted indeno[1,2-c]- pyrazol-4-one derivatives of form.la:
wherein R is hydrogen, ethyl, ethoxycarbonyl or benzoyl and R1 is t-butyl, phenyl, p-methoxyphenyl or phenyl are described in J. Org. Chem. 24, 648-650 (1959) as fluorescent compounds. No biological activity is ascribed to the compounds. US-A-2,969,371, US-A-2,969,373 and US-A-2,969,374 describe various 3-substituted and 1,3disubstituted indenoll,2-czpyrazol-4-one derivatives in which the 1-substituent can be an acyl group.These patent documents describe the derivatives in question only as intermediates in the preparation of indenoll,2-c]pyrazol-4- one hydrazones or azines, optionally substituted in the benzene ring of the indanone moiety, and ascribe pharmacological activity to the hydrazones and azines. US-A-2,969,372 describes, again only as intermediates in the preparation of pharmacologically active hydrazones, various 3-substituted and 1,3-disubstituted indenoll,2-c]pyrazol-4- one derivatives in which the 3-substituent is cycloalkyl and the 1-substituent can be acyl.
It has now been found that certain 1,3-disubstituted indeno[l,2-c]pyrazol-4-one derivatives have useful herbicidal properties. Accordingly the invention provides a herbicidal composition which comprises a carrier and, as active ingredient, at least one indeno!1,2-cpyrazol-4-one derivative of formula (I):
wherein Ri is an acyl group, R2 is an optionally substituted alkyl or cycloalkyl group and X represents halogen, nitro, alkyl, haloalkyl, alkoxy or haloalkoxy, and n is 0, 1 or 2.
By "acyl" we mean an organic group derived by removal of an hydroxyl group from an organic acid.
Preferred acyl groups for Rl are those derived from organic carboxylic, including carbamic, acids and sulfonic acids, especially acyl groups of the formula R3 CO- and R3SO2-, wherein R3 is alkyl haloalkyl, optionally substituted aryl (preferably phenyl), optionally substituted aromatic heterocycle (preferably of 5 or 6 ring atoms, especially 2 thienyl) or optionally substituted amino (such as alkylamino and dialkylamino). Suitable substituents for the aryl and aromatic heterocyclic groups include halogen, especially chlorine or fluorine, nitro, alkoxy, haloalkoxy, alkyl, especially methyl, ethyl, and isopropyl, and haloalkyl, especially trifluoromethyl.Although more than one substituent may be present it is preferred that any aryl or aromatic heterocyclic group present as R3 should be unsubstituted or monosubstituted.
Preferably R2 is an alkyl or haloalkyl group, especially a branched chain such group, most preferably t-butyl.
The benzene ring of the indanone moiety is preferably unsubstituted (i.e. n is zero) but may be monoor disubstituted by halogen, especially chlorine or fluorine, nitro, alkoxy, haloalkoxy, alkyl, especially methyl, ethyl or isopropyl, or haloalkyl, especially trifluoromethyl.
When an alkyl moiety is present, as such or in an alkoxy, haloalkoxy or haloalkyl group, in the compounds of formula (I) they suitably have up to 10, preferably up to 6, and especially up to 4, carbon atoms.
The compounds of formula (I) may be prepared in accordance with known methods, in particular in accordance with methods described in the prior art documents referred to above, and in US-A-2,989,538. In general the method for preparing a compound of formula (I) comprises two stages, a first stage involving the preparation of a 3-substituted indeno[l,2-c]pyrazol-4-one derivative and the second stage involving the introduction of the l-substituent. The first stage comprises reacting a 2-acyl-1,3-indandione with about one molar equivalent of hydrazine in accordance with the following reaction scheme:
This reaction is preferably carried out at elevated temperatures, such as from 40 C to 1300C, from 30 minutes to 24 hours in a suitable inert solvent in which the reactants are substantially soluble.Usually a polar organic solvent is used, such as the preferred lower (C1 - C4 ) alcohols, especially methanol and ethanol or mixtures thereof.
Alternatively, however, benzene, tetrahydrofuran, toluene, xylene or other such solvents can be used. The hydrazine reactant may be either pure hydrazine or the hydrate.
Small amounts of hydrazone impurities are formed as byproducts in some cases. The reaction mixture is conveniently worked up by diluting the mixture with water, separating the resulting solid and fractionally crystallizing the intermediate of formula (II).
The second stage is preferably carried out by reacting the intermediate of formula (II) with a basic reagent, preferably an alkali metal or hydroxide, amide, carbonate or, especially, hydride, to form an N-metal salt at the l-position, preferably an alkali metal, especially sodium, potassium or lithium, salt. This N-metal salt is then reacted with an acylating agent of formula R1Y, wherein Rl is the desired l-substituent as previously defined and Y is a leaving group or atom, preferably halogen and especially chlorine, Lo provide the desired compound of formula (I).
The compounds of the general formula (I) have been found to possess useful herbicidal properties, and accordingly the invention provides a herbicidal composition containing such a compound. Further, in accordance with the invention, there is provided a method of combating undesired plant growth at a locus by treating the locus with a compound of formula (I) or composition containing such a compound. Application to the locus may be pre-emergence or post-emergence. The dosage of active ingredient used may, for example, be from 0.05 to 4kg/ha. A carrier in a composition according to the invention is any material with which the active ingredient is formulated to facilitate application to the locus to be treated, which may for example be a plant, seed or soil, or to facilitate storage, transport or handling.A carrier may be a solid or a liquid, including a material which is normally gaseous but which has been compressed to form a liquid, and any of the carriers normally used in formulating herbicidal compositions may be used. Preferably compositions according to the invention contain 0.5 to 95% by weight of active ingredient.
Suitable solid carriers include natural and synthetic clays and silicates, for example natural silicas such as diatomaceous earths; magnesium silicates, for example talcs; magnesium aluminium silicates, for example attupulgites and vermiculites; aluminium silicates, for example kaolinites, montmorillonites and micas; calcium carbonate; calcium sulphate; ammonium sulphate; synthetic hydrated silicon oxides and synthetic calcium or aluminium silicates; elements, for example carbon and sulphur; natural and synthetic resins, for example coumarone resins, polyvinyl chloride, and styrene polymers and copolymers; solid polychlorophenols; bitumen; waxes; and solid fertilisers, for example superphosphates.
Suitable liquid carriers include water; alcohols, for example isopropanol and glycols; ketones, for example acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; ethers; aromatic or araliphatic hydrocarbons, for example benzene, toluene and xylene; petroleum fractions, for example kerosine and light mineral oils; chlorinated hydrocarbons, for example carbon tetrachloride, perchloroethylene and trichloroethane. Mixtures of different liquids are often suitable.
Agricultural compositions are often formulated and transported in a concentrated form which is subsequently diluted by the user before application. The presence of small amounts of a carrier which is a surface-active agent facilitates this process of dilution. Thus preferably at least one carrier in a composition according to the invention is a surface-active agent. For example the composition may contain at least two carriers, at least one of which is a surface-active agent.
A surface-active agent may be an emulsifying agent, a dispersing agent or a wetting agent; it may be nonionic or ionic. Examples of suitable surface-active agents include the sodium or calcium salts of polyacrylic acids and lignin sulphonic acids; the condensation of fatty acids or aliphatic amines or amides containing at least 12 carbon atoms in the molecule with ethylene oxide and/or propylene oxide; fatty acid esters of glycerol, sorbitan, sucrose or pentaerythritol; condensates of these with ethylene oxide and/or propylene oxide; condensation products of fatty alcohol or alkyl phenols, for example g-octylphenol or p-octylcresol, with ethylene oxide and/or propylene oxide; sulphates or sulphonates of these condensation products; alkali or alkaline earth metal salts, preferably sodium salts, of sulphuric or sulphonic acid esters containing at least 10 carbon atoms in the molecule, for example sodium lauryl sulphate, sodium secondary alkyl sulphates, sodium salts of sulphonated castor oil, and sodium alkylaryl sulphonates such as dodecylbenzene sulphonate; and polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide.
The compositions of the invention may for example be formulated as wettable powders, dusts, granules, solutions, emulsifiable concentrates, emulsions, suspension concentrates and aerosols. Wettable powders usually contain 25, 50 or 75% w of active ingredient and usually contain in addition to solid inert carrier, 3-10% w of a dispersing agent and, where necessary, 0-10% w of stabiliser(s) and/or other additives such as penetrants or stickers. Dusts are usually formulated as a dust concentrate having a similar composition to that of a wettable powder but without a dispersant, and are diluted in the field with further solid carrier to give a composition usually containing 1/2-10% w of active ingredient. Granules are usually prepared to have a size between 10 and 100 BS mesh (1.676 - 0.152 mm), and may be manufactured by agglomeration or impregnation techniques.Generally, granules will contain 1/2-75% w active ingredient and 0-10% w of additives such as stabilisers, surfactants, slow release modifiers and binding agents. The so-called "dry flowable powders" consist of relatively small granules having a relatively high concentration of active ingredient. Emulsifiable concentrates usually contain, in addition to a solvent and, when necessary, co-solvent, 10-5-% w/v active ingredient, 2-20% w/v emulsifiers and 0-20% w/v of other additives such as stabilisers, penetrants and corrosion inhibitors.
Suspension concentrates are usually compounded so as to obtain a stable, non-sedimenting flowable product and uaually contain 10-75% w active ingredient, 0.5-15% w of dispersing agents, 0.1-108 w of suspending agents such as protective colloids and thixotropic agents, 0-10% w of other additives such as defoamers, corrosion inhibitors, stabilisers, penetrants and stickers, and water or an organic liquid in which the active ingredient is substantially insoluble; certain organic solids or inorganic salts may be present dissolved in the formulation to assist in preventing sedimentation or as anti-freeze agents for water.
Aqueous dispersions and emulsions, for example compositions obtained by diluting a wettable powder or a concentrate according to the invention with water, also lie within the scope of the invention. The said emulsions may be of the water-in-oil or of the oil-in-water type, and may have a thick 'mayonnaise'-like consistency.
The composition of t.e invention may also contain other ingredients, for example other compounds possessing herbicidal, insecticidal or fungicidal properties.
Representative compounds of formula (I) which may be used as the active ingredient of a herbicidal composition in accordance with the invention are as summarized in Table I which follows. In all of these compounds the benzene ring of the indanone moiety is unsubstituted (i.e. n is zero).
A representative prepa-ative method for one of the compounds (Example 5) is also given below.
TABLE I
Example R1 R2 Elemetal Analysis MOL WT Calculated Found Calc Found No. C H N C H N 1 ClCH2CO- tC4H9- 63.5 5.0 9.3 302 302 2 C6H5CO- tC4H9- 76.4 5.45 8.5 76.1 5.5 8.6 330 330 3 #-CO- tC4H9- 67.8 4.8 8.3 67.3 4.8 8.9 336 336 4 4Cl-PhenylCO tC4H9- 69.1 4.7 7.7 69.1 4.7 7.7 364 364 5 C2H5CO-2 tC4H9- 72.3 6.4 9.9 72.4 6.6 10.1 282 282 6 nC3H7CO- tC4H9- 72.9 6.8 9.5 71.8 6.7 9.5 296 296 7 iC3H7CO- tC4H9- 70.8 5.5 11.0 70.5 5.5 11.1 296 296 8 nC4H9CO- tC4H9- 73.5 7.1 9.0 73.3 7.2 9.3 310 310 TABLE I (Continued)
Example R1 R2 Elemetal Analysis MOL WT Calculated Found Calc Found No. C H N C H N 9 nC5H11CO- tC4H9- 74.0 7.5 8.6 74.1 7.5 8.9 324 324 10 C2H5CO- C2H5- 70.8 5.5 11.0 70.4 5.5 11.1 254 254 11 nC3H7CO- iC3H7- 72.3 6.4 9.9 71.9 6.4 9.9 282 282 12 nC5H11CO- nC3H7- 73.5 7.1 9.0 72.3 7.0 8.9 310 310 13 tC4H9CO- tC4H9- 73.5 7.1 9.0 73.2 7.2 9.1 310 310 14 Ch3NHCO- tC4H9- 67.8 6.0 14.8 67.9 6.2 15.1 283 283 15 (CH3)2NCO- tC4H9- 68.7 6.4 14.1 68.8 6.5 14.2 297 297 TABLE I (Continued)
Example R1 R2 Elemetal Analysis MOL WT Calculated Found Calc Found No. C H N C H N 16 nC4H9NHCO- tC4H9- 70.1 7.1 12.9 70.6 7.0 12.8 325 325 17 CH3CH2C(CH3)2CO- tC4H9- 74.1 7.4 8.6 73.9 7.5 8.7 324 324 18 (CH3CH2)2(CH3)CCO- tC4H9- 74.55 7.7 8.3 74.7 7.9 8.3 338 338 19 CH3CH2CH2C(CH3)2CO- tC4H9- 74.55 7.7 8.3 74.0 7.8 8.1 338 338 20 tC4H9CO- CH3- 71.6 6.0 10.4 71.3 6.2 11.0 268 268 21 CH3NHCO- CH3- 64.7 4.6 17.4 65.5 4.9 17.4 241 241 Preparation of compound 5 3-t-Butylindeno[1,2-c]pyrazolo-4(1H)one (1.0g) was dissolved in ether (50 mls) and the solution cooled in ice/water. Triethylamine (1.0 mls) was added. Propionylchloride (0.4 mls) in ether (10 mls) was added dropwise with stirring during 20 minutes.
Stirring was continued at ambient temperature overnight. The ether solution was washed twice with water, the combined washes back-extracted once with ether and the combined ether solutions dried over MgSO4, filtered and ether removed in vacuo. The bright yellow solid (1.3g, 95%) that remained had Tnpt 122.5-124C and was pure by analysis.
(3-substituted indeno[1,2-c]pyrazolo-4(1H)-ones were prepared by reaction of an appropriate methyl ketone with a diester of phthalic acid followed by reaction with hydrazine as described in U.S. Patent 2,969,371).
Herbicidal Activity To evaluate their herbicidal activity, compounds of formula (I) were tested using as a representative range of plants: maize, Zea mays (Mz); rice, Oryza sativa (R); barnyard grass, Echinochloa crusgalli (BG); oat, Avena sativa (0); linseed, Linum usitatissisum (L); mustard, Sinapsis alba (M); sugar beet, Beta vulgaris (SB) and soya bean, Glycine max (S).
The tests fall into two categories, pre-emergence and post-emergence. The pre-emergence tests involved spraying a liquid formulation of the compound onto the soil in which the seeds of the plant species mentioned above had recently been sown. The post-emergence tests involved two types of test, viz., soil drench and foliar spray tests. In the soil drench tests the soil in which the seedling plants of the above species were growing was drenched with a liquid formulation containing a compound of the invention, and in the foliar spray tests the seedling plants were sprayed with such a formulation.
The soil used in the tests was a prepared horticultural loam.
The formulations used in the tests were prepared from solutions of the test compounds in acetone containing 0.4% by weight of an alkylphenol/ethylene oxide condensate available under the trade mark TRITON X-155. These acetone solutions were diluted with water and the resulting formulations applied at dosage levels corresponding to 5 kg or 1 kg of active material per hectare in a volume equivalent to 600 litres per hectare in the soil spray and foliar spray tests, and at a dosage level equivalent to 10 kilograms of active material per hectare in a volume equivalent to approximately 3,000 litres per hectare in the soil drench tests.
In the pre-emergence tests untreated sown soil and in the post-emergence tests untreated soil bearing seedling plants were used as controls.
The herbicidal effects of the test compounds were assessed visually twelve days after spraying the foliage and the soil, and thirteen days after drenching the soil and were recorded on a 0-9 scale. A rating 0 indicates growth as untreated control, a rating 9 indicates death. An increase of 1 unit on the linear scale approximates to a 10% increase in the level of effect.
The results of the tests are set out in Table II below.
TABLE II
Compound of Phytotoxicity Rating (0-9) Example No. Dose Post-emergence (plants) seeds Kg/ha Soil drech 10/Kg/ha Foliar spray Pre-emergence Mz R BG O L M SB S Mz R BG O L M SB S Mz R BG O L M SB S 1(1) 5 0 0 5 0 3 6 7 2 4 3 9 8 9 9 9 7 0 0 5 0 2 8 8 0 1 2 2 8 7 8 9 9 6 0 0 3 0 0 5 3 0 2 5 0 0 0 0 0 6 7 1 4 4 9 8 9 9 9 7 0 0 0 0 0 0 0 0 1 2 3 8 6 8 9 9 6 0 0 0 0 0 0 0 0 3 5 0 0 0 0 0 0 0 0 0 0 7 5 8 8 8 4 0 0 0 0 0 0 0 0 1 0 0 4 2 6 6 6 3 0 0 0 0 0 0 0 0 4 5 0 0 0 0 0 0 0 0 4 0 8 4 6 9 9 5 0 0 0 0 0 0 0 0 1 0 0 6 3 5 8 8 2 0 0 0 0 0 0 0 0 TABLE II (Contd.)
Compound of Phytotoxicity Rating (0-9) Example No. Dose Post-emergence (plants) seeds Kg/ha Soil drench 10/Kg/ha Foliar spray Pre-emergence Mz R BG O L M SB S Mz R BG O L M SB S Mz R BG O L M SB S 5 5 0 0 0 0 0 4 5 2 2 2 9 8 9 9 9 7 0 0 0 0 4 8 9 0 1 1 1 7 5 7 9 9 5 0 0 0 0 1 5 5 0 6 5 0 0 0 0 0 6 4 2 2 2 9 8 9 9 9 6 0 0 0 0 2 7 8 0 1 0 1 7 5 6 9 9 3 0 0 0 0 0 5 6 0 7 5 0 0 0 0 0 0 4 0 4 2 9 8 8 9 9 7 0 0 0 0 2 7 9 0 1 1 0 6 5 6 8 9 4 0 0 0 0 1 2 2 0 8 5 0 0 0 0 0 0 0 0 2 3 9 8 8 9 9 7 0 0 0 0 2 8 9 0 1 1 0 8 6 7 9 9 5 0 0 0 0 1 4 4 0 9 5 0 0 0 0 0 0 4 0 2 1 9 8 9 9 9 7 0 0 0 0 2 8 8 0 1 1 0 8 6 7 9 9 5 0 0 0 0 0 2 3 0 11 5 0 3 0 0 0 3 8 0 1 0 2 4 3 2 6 9 3 0 0 0 0 0 0 0 0 TABLE II (Contd.)
Compound of Phytotoxicity Rating (0-9) Example No. Dose Post-emergence (plants) seeds Kg/ha Soil drench 10/Kg/ha Foliar spray Pre-emergence Mz R BG O L M SB S Mz R BG O L M SB S Mz R BG O L M SB S 12 5 0 0 0 0 0 0 0 0 2 5 3 3 4 6 6 3 0 0 0 0 0 0 0 0 1 0 1 1 0 2 2 2 1 0 0 0 0 0 0 0 0 13 5 0 0 0 0 0 3 0 0 2 3 9 8 9 9 9 6 0 0 9 8 2 9 9 0 1 0 1 9 8 8 9 8 4 0 0 4 1 0 7 9 0 14 5 0 0 0 0 0 0 0 0 1 2 8 4 6 7 7 3 0 0 0 3 0 0 0 0 1 0 1 3 3 4 6 7 2 0 0 0 0 0 0 0 0 15 5 0 0 0 0 0 0 0 0 0 2 8 6 8 9 7 3 0 0 0 0 0 3 9 0 1 0 1 5 3 4 7 5 2 0 0 0 0 0 0 0 0 17 5 0 0 0 0 0 0 0 0 2 1 8 6 7 9 9 2 0 0 0 0 0 9 9 0 1 0 0 3 1 2 8 6 2 0 0 0 0 0 8 7 0 TABLE II (Contd.)
Compound of Phytotoxicity Rating (0-9) Example No. Dose Post-emergence (plants) seeds Kg/ha Soil drench 10/Kg/ha Foliar spray Pre-emergence Mz R BG O L M SB S Mz R BG O L M SB S Mz R BG O L M SB S 19 5 0 0 0 0 0 0 0 0 4 4 6 8 8 9 9 5 0 0 0 0 0 6 0 0 1 1 1 1 2 3 8 6 2 0 0 0 0 0 1 0 0 NOTE: (1) Composition sprayed immediately after solution.
Comparative Examples A to E Compounds structurally closely related to compounds of formula (I) were tested in similar manner for herbicidal activity. The compounds used were as follows: Comparative Example A n n B n C " "
The following results obtained are set out in Table III below. TABLE III
Compound of Phytotoxicity Rating (0-9) Example No. Dose Post-emergence (plants) seeds Kg/ha Soil drench 10/Kg/ha Foliar spray Pre-emergence Mz R BG O L M SB S Mz R BG O L M SB S Mz R BG O L M SB S A 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 B 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 C 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 D 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 E 5 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Claims (6)

1. A herbicidal composition which comprises a carrier and, as active ingredient, at least one indeno (1,2-cpyrazol-4-one derivative of formula (I):
wherein Rl is an acyl group, R2 is an optionally substituted alkyl or cycloalkyl group and X represents halogen, nitro, alkyl, haloalkyl, alkoxy or haloalkoxy, and n is 0, 1 or 2.
2. A herbicidal composition according to claim 1 wherein R1 is an acyl group of formula R3 CO- or R,SO,-, wherein R3 is alkyl, haloalkyl, optionally substituted aryl, optionally substituted aromatic heterocycle or optionally substituted amino.
3. A herbicidal composition according to claim 2 wherein R3 is Cl - C6 alkyl or haloalkyl, phenyl, chlorophenyl, 2-thienyl, amino, C1 - C6 alkylamino or di (Cl - C6 alkyl)amino.
4. A herbicidal composition according to claim 1, 2 or 3 wherein R2 is C1 - C6 alkyl or haloalkyl.
5. A herbicidal composition according to claim 4 wherein R3 is a branched chain alkyl, preferably t-butyl.
6. A method of preventing or combating undesired plant growth at a locus which comprises treating said plant growth or locus with a herbicidal composition as claimed in any one of the preceding claims.
GB8824836A 1988-10-24 1988-10-24 Herbicidal compositions and their use Withdrawn GB2223946A (en)

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Cited By (8)

* Cited by examiner, † Cited by third party
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US5637554A (en) * 1993-01-20 1997-06-10 Basf Aktiengesellschaft 5-substituted 4-methyl-5H-indeno[3,2-b]pyridines and 9-substituted 1-methyl-9H-indeno[2,3-c]pyridines, their preparation and use as herbicides and plant growth regulators
EP0862860A3 (en) * 1997-03-04 1999-02-24 Rohm And Haas Company Indanone herbicide compositions and use thereof
US6291504B1 (en) 1999-10-20 2001-09-18 Dupont Pharmaceuticals Company Acylsemicarbazides and their uses
US6407103B2 (en) 1998-04-21 2002-06-18 Bristol-Myers Squibb Pharma Company Indeno [1,2-c] pyrazol-4-ones and their uses
US6413957B1 (en) 1998-04-21 2002-07-02 Bristol-Myers Suibb Pharma Company Methods of inhibiting cell proliferation using indeno [1,2-c]pyrazol-4-ones
US6706718B2 (en) 2000-12-01 2004-03-16 Bristol-Myers Squibb Company 3-(2,4-dimethylthiazol-5-yl)indeno[1,2-c]pyrazol-4-one derivatives and their uses
US6849631B2 (en) 2000-12-08 2005-02-01 Bristol Myers Squibb Pharma Company Semicarbazides and their uses
US7250435B2 (en) 1999-10-20 2007-07-31 Bristol-Myers Squibb Pharma Company Acylsemicarbazides as cyclin dependent kinase inhibitors useful as anti-cancer and anti-proliferative agents

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5637554A (en) * 1993-01-20 1997-06-10 Basf Aktiengesellschaft 5-substituted 4-methyl-5H-indeno[3,2-b]pyridines and 9-substituted 1-methyl-9H-indeno[2,3-c]pyridines, their preparation and use as herbicides and plant growth regulators
EP0862860A3 (en) * 1997-03-04 1999-02-24 Rohm And Haas Company Indanone herbicide compositions and use thereof
US6025301A (en) * 1997-03-04 2000-02-15 Rohm And Haas Company Indanone herbicide compositions and use thereof
US6407103B2 (en) 1998-04-21 2002-06-18 Bristol-Myers Squibb Pharma Company Indeno [1,2-c] pyrazol-4-ones and their uses
US6413957B1 (en) 1998-04-21 2002-07-02 Bristol-Myers Suibb Pharma Company Methods of inhibiting cell proliferation using indeno [1,2-c]pyrazol-4-ones
US6291504B1 (en) 1999-10-20 2001-09-18 Dupont Pharmaceuticals Company Acylsemicarbazides and their uses
US7250435B2 (en) 1999-10-20 2007-07-31 Bristol-Myers Squibb Pharma Company Acylsemicarbazides as cyclin dependent kinase inhibitors useful as anti-cancer and anti-proliferative agents
US6706718B2 (en) 2000-12-01 2004-03-16 Bristol-Myers Squibb Company 3-(2,4-dimethylthiazol-5-yl)indeno[1,2-c]pyrazol-4-one derivatives and their uses
US6849631B2 (en) 2000-12-08 2005-02-01 Bristol Myers Squibb Pharma Company Semicarbazides and their uses

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