WO1998013341A1 - Derives d'hydroxybenzophenones en tant qu'herbicides - Google Patents

Derives d'hydroxybenzophenones en tant qu'herbicides Download PDF

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Publication number
WO1998013341A1
WO1998013341A1 PCT/EP1997/005210 EP9705210W WO9813341A1 WO 1998013341 A1 WO1998013341 A1 WO 1998013341A1 EP 9705210 W EP9705210 W EP 9705210W WO 9813341 A1 WO9813341 A1 WO 9813341A1
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Prior art keywords
hydrogen
alkyl
halogen
formula
methyl
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PCT/EP1997/005210
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English (en)
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WO1998013341B1 (fr
Inventor
Susan Mary Cramp
Fabrice Viviani
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Rhone-Poulenc Agriculture Ltd.
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Priority to AU47051/97A priority Critical patent/AU4705197A/en
Publication of WO1998013341A1 publication Critical patent/WO1998013341A1/fr
Publication of WO1998013341B1 publication Critical patent/WO1998013341B1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
    • 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups

Definitions

  • This invention relates to novel hydroxybenzophenone derivatives, compositions containing them, processes and intermediates for their preparation, and their use as herbicides.
  • the present invention provides hydroxybenzophenone derivatives of formula (I):
  • R 1 represents :- straight- or branched- chain halogenated alkyl containing up to four carbon atoms and at least two halogen atoms; or a member of the group consisting of -N0 , R 9 S(0) m -, R 9 S0 2 -0-, R 9 S(0) m -CH(R 10 ) -, (R 9 0) (R 1:L 0)P(0) -, (R 9 0) (R ⁇ : 0)P(0) -CH(R 10 ) -, R 10 R 12 NC(O)N(R 10 ) -, R 13 XCCO)N(R 10 ) -, R 9 R 1:L NS0 2 -, R 14 S0 2 N (R 10 ) - , -SF 5 , Het-CH(R 10 ) -, R 9 S(0) m -CH 2 CH 2 - and benzyl optionally substituted by one or more groups R 15 which may be the same or different
  • R 2 and R 3 independently represent : -
  • R 1 hydrogen, halogen, straight- or branched- chain alkyl containing up to four carbon atoms optionally halogenated with one halogen; straight- or branched- chain optionally halogenated alkoxy containing up to four carbon atoms; straight- or branched- chain alkyl containing up to six carbon atoms which is substituted by one or more -OR 1 ⁇ groups,- or a member of the group consisting of cyano, R 9 C(0)-, R 9 XC(0)-, R 10 R 12 NC(O) -, R 13 C (0) N (R 10 ) - and NR 10 R 12 ; wherein the ortho position of the phenyl ring is substituted by a non-hydrogen substituent;
  • R 4 represents :- hydrogen, R 13 , straight- or branched- chain alkyl containing up to six carbon atoms which is substituted by one or more -XR 16 groups; or a member of the group consisting of R 9 S0 2 -, R 9 C(0)- and R 10 C(O)C(R 10 ) (R 12 ) -;
  • R 5 , R 6 and R 7 independently represent: - hydrogen, halogen, hydroxy, R 16 SO m -, R 13 , straight- or branched- chain optionally halogenated alkoxy containing one to four carbon atoms; straight- or branched- chain alkyl containing up to six carbon atoms which is substituted by one or more -OR 16 ; or a member of the group consisting of -N0 2 , cyano,
  • R 14 S0 2 N(R 10 ) -, R 9 C(0)-, R 9 XC(0)-, R 9 C (0) N (R 10 ) - , R 10 R 12 NC(O) -, R 10 R 12 NC(O)N(R 10 ) -, R 10 R 12 NS0 2 -, and cycloalkyl containing from three to six ring carbon atoms,- R 8 is as defined for R 5 with the exclusion of hydroxy;
  • R 9 and R independently represent : - straight- or branched- chain optionally halogenated alkyl containing up to four carbon atoms ; or phenyl or benzyl which are optionally substituted by one to five groups R 15 which may be the same or different;
  • R 10 and R 12 independently represent hydrogen or R 9 ;
  • R 13 represents straight- or branched- chain optionally halogenated alkyl containing up to four carbon atoms
  • R 14 represents straight- or branched- chain alkyl containing up to four carbon atoms
  • R 15 represents halogen, optionally halogenated methyl; or R 14 SO m - ; R 16 represents straight- or branched- chain alkyl containing up to six carbon atoms,-
  • Het represents a five me bered aromatic heterocyclic ring containing from one to three ring nitrogen atoms which is attached to the -CH(R 10 )- group via one of the ring nitrogen atoms ;
  • X represents oxygen or sulphur
  • m represents the values 0,1, or 2; with the proviso that: (a) when R 1 represents nitro it is located at the 2 -position of the phenyl ring and that at least one of R 2 and R 3 represents halogen, R 9 S(0) m -, or straight- or branched- chain halogenated alkyl containing up to four carbon atoms;
  • R 1 is not 2-SOMe, 2-S0 2 Me or 2-S- (4-methylphenyl) ;
  • R 1 when R 1 represents 2-CF3 and each of R 2 to R 6 and R 8 represent hydrogen, R 7 is not chloro or hydroxy; (e) when R 1 represents 2-CF3.
  • R 7 and R 8 each represent hydrogen and R 5 represents chloro, R 6 is not methoxy;
  • R 1 when R 1 represents 2-CF3; R 2 , R 3 , R 5 and R 8 each represent hydrogen and R 6 represents methoxy, R 4 is not hydrogen or methyl; (h) when R 1 represents 2-CF 3 ; R 2 , R 3 , R 5 , R 6 and R 8 each represent hydrogen and R 4 represents methyl, R 7 is not methoxy;
  • R 1 represents 2-CF3
  • R 2 , R 3 and R 7 each represent hydrogen
  • R 4 represents methyl
  • R 5 and R 6 each represent methoxy
  • R 8 is not methyl
  • agriculturally acceptable salts thereof, which possess valuable herbicidal properties.
  • a number of the substituents may result in the compounds of the invention existing as optical and/or stereo isomers. All such forms are embraced by the present invention.
  • agriculturally acceptable salts is meant salts the cations or anions of which are known and accepted in the art for the formation of salts for agricultural or horticultural use.
  • the salts are water-soluble.
  • Suitable salts with bases include alkali metal (e.g. sodium and potassium), alkaline earth metal (e.g. calcium and magnesium), ammonium and amine (e.g. diethanolamine, triethanolamine, octylamine, morpholine and dioctylmethylamine) salts.
  • Suitable acid addition salts include salts with inorganic acids, for example hydrochloride ⁇ , sulphates, phosphates and nitrates and salts with organic acids for example acetic acid.
  • R 1 is straight- or branched- chain haloalkyl containing up to four carbon atoms; or R 9 S(0) m - wherein m is as defined above and R 9 is straight- or branched- chain alkyl containing up to four carbon atoms are preferred.
  • R 1 or R 2 occupies the ortho- position of the phenyl ring (compounds in which R occupies the ortho- position are especially preferred) .
  • R 2 is optionally halogenated alkoxy or (most preferably) hydrogen; and/or R 3 is hydrogen, halogen or haloalkoxy.
  • R 1 represents C1-C3 alkyl containing at least two halogen atoms (for example trifluoromethyl) , -S(0) m R 9 (wherein R 9 represents C1-C3 alkyl), -CH(R 10 ) -S (0) m -R 9 (wherein R 9 represents C1-C3 alkyl or phenyl, and R 10 represents hydrogen or methyl) , N0 or R 14 S0 2 N(R 10 ) - (wherein R 14 and R 10 represent Cl- C3 alkyl) ;
  • R 2 and R 3 independently represent C1-C3 optionally halogenated alkyl (for example methyl or trifluoromethyl) , hydrogen, halogen, C1-C3 optionally halogenated alkoxy or -S(0) m R 9 (wherein R 9 represents C1-C3 alkyl) ;
  • R 4 represents hydrogen, C1-C3 alkyl, R 9 S0 - (wherein R 9 represents C1-C3 alkyl or phenyl optionally substituted by one to five halogen, methyl or R 1 S(0) m - groups wherein R 14 represents C1-C3 alkyl), R 9 C(0)- (wherein R 9 represents C1-C3 alkyl or phenyl optionally substituted by one to five halogen or C1-C3 alkyl groups), R 10 C(O)CH 2 - (wherein R 10 represents phenyl optionally substituted by one or more halogen or C1-C3 alkyl groups) , or methyl substituted by -XR 16 wherein R 16 represents C1-C3 alkyl; R 5 , R 6 and R 7 independently represent hydrogen, halogen, hydroxy, C1-C3 alkoxy or R 16 S(0) m - wherein R 16 represents C1-C3 alkyl; and R 8 represents hydrogen or halogen.
  • R 1 which represents -S(0) m -R 9 (wherein R 9 represents Cl-C3-alkyl) , -CH(R 10 ) -S(0) m -R 9 (wherein R 9 represents C1-C3- alkyl or phenyl and R 10 represents hydrogen or methyl), or R 14 S0 2 N(R 10 ) - (wherein R 10 and R 14 represent C1-C3 alkyl) are also preferred.
  • a preferred class of compounds are those in which:
  • R 4 represents hydrogen
  • R 5 , R 6 and R 7 represent hydrogen, halogen, hydroxy, R 16 S(0) m -, R 13 , straight- or branched- chain optionally halogenated alkoxy containing up to four carbon atoms, straight- or branched- chain alkyl containing up to six carbon atoms which is substituted by one or more OR 16 groups, -N0 2 , cyano, or R 10 R 12 NSO 2 - ; and
  • R 8 is as defined for R 5 excluding hydroxy.
  • a further preferred class of compounds are those having one or more of the following features :
  • R 1 represents MeS(0) m - or -CF3.
  • R 2 , R 4 and R 8 each represent hydrogen
  • R 3 represents hydrogen or -CF 3 ;
  • R 5 represents hydrogen, halogen, hydroxy or methoxy;
  • R 6 represents hydrogen or MeS(0) m -
  • R 7 represents hydrogen, halogen or methyl.
  • a further preferred class of compounds are those in which: the ortho- sub ⁇ tituent of the phenyl ring bearing R 1 , R 2 or R 3 is -S(0) m R 9 (wherein R 9 represents C1-C3 alkyl), -CH (R 10 ) -S (0) m -phenyl (wherein R 10 repre ⁇ ent ⁇ hydrogen or methyl) , Cl- C3 haloalkyl (for example trifluoromethyl) ,
  • R 14 S0 2 N(R 10 ) - (wherein R 14 and R 10 represent Cl- C3 alkyl) or C1-C3 alkyl (for example methyl) ; the para-substituent of the phenyl ring bearing R 1 , R 2 or R 3 i ⁇ hydrogen, halogen, C1-C3 haloalkyl (for example trifluoromethyl) or
  • R 9 represents C1-C3 alkyl
  • the meta-substituent of the phenyl ring is selected from hydrogen, halogen, C1-C3 optionally halogenated alkoxy (for example methoxy or 2, 2-difluoroethoxy) and C1-C3 alkyl;
  • R 4 represents hydrogen or C1-C3 alkyl (for example methyl) ;
  • R 5 represents hydrogen, halogen, hydroxy or C1-C3 alkoxy (for example methoxy) ⁇
  • R ⁇ represents hydrogen, halogen or R 16 S(0) m - wherein R 16 represents C1-C3 alkyl; R 7 represents hydrogen, halogen or C1-C3 alkoxy (for example methoxy) ; and
  • R 8 represents hydrogen
  • compounds of formula (I) may be prepared by the reaction of a compound of general formula (II):
  • R 4 as defined above and Y represents a leaving group (for example chlorine or -NR 17 R 18 wherein R 17 represents lower alkyl, preferably methyl, and
  • R 18 represents lower alkyl or preferably alkoxy, methoxy being especially preferred) , with an organometallic reagent of formula (III):
  • R 1 , R 2 and R 3 are as defined above and M is a suitable metal, preferably lithium.
  • the reaction is generally performed in an inert solvent (for example ether) at a temperature from -78°C to 30°C.
  • compounds of formula (I) may be prepared by the reaction of a compound of general formula (I la) :
  • reaction is generally performed in an inert solvent (for example ether or tetrahydrofuran) at a temperature from -78 °C to 30°C.
  • inert solvent for example ether or tetrahydrofuran
  • compounds of formula (I) wherein R 1 , R 2 , R 3 , R 5 , R 6 , R 7 and R 8 are as defined above and R 4 represents hydrogen may be prepared by de-etherification of the corresponding compound of formula (I) in which R 4 represents R 13 , preferably methyl.
  • This reaction is generally carried out with a boron trihalide of formula BZ3 wherein Z represents halogen, preferably bromine.
  • the reaction is generally performed in an inert solvent, for example dichloromethane, at a temperature from -78°C to 30°C.
  • compounds of formula (I) wherein R 1 , R 2 , R 3 , R 5 , R 6 , R 7 and R 8 are as defined above and R 4 represents R 9 S0 may be prepared by reaction of the corresponding compound of formula (I) in which R 4 represents hydrogen with a sulphonyl chloride of formula R 9 S0 C1 in which R 9 is as defined above.
  • the reaction is generally performed in the presence of a base, for example pyridine, in an inert solvent, for example dichloromethane, at a temperature from 0°C to 30°C.
  • compounds of formula (I) wherein R 1 , R 2 , R 3 , R 5 , R 6 , R 7 and R 8 are as defined above and R 4 represents R 10 C(0)C(R 10 ) (R 12 )-, wherein R 10 and R 12 are as defined above may be prepared by the reaction of the corresponding compound of formula (I) in which R 4 represents hydrogen, with a compound of formula (IV) :
  • R l -> and R 12 are as defined above and Z represents halogen preferably chlorine.
  • the reaction is generally performed in the presence of a base, for example potassium carbonate, in an inert solvent, for example acetone, at a temperature from 20°C to 120°C.
  • a base for example potassium carbonate
  • an inert solvent for example acetone
  • compounds in which m is one or two may be prepared by the oxidation of the sulphur atom of the corresponding compounds in which m is zero or one.
  • the oxidation of the sulphur atom is generally carried out using for example 3-chloroperoxybenzoic acid in an inert solvent such as dichloromethane at a temperature from -40°C to room temperature.
  • N-methoxy-N-methyl-2-methoxy-4- (methylthio)benzamide NMR 2.41 (s,3H), 3.2 (br s , 3H ) , 3 . 5 (br s , 3H ) , 3 . 76 ( ⁇ , 3H ) , 6 . 75 (m, 2H ) , 7 . 1 - 7 . 2 (m, lH) ;
  • N-methoxy-N-methyl-2, 3-dimethoxybenzamide NMR 3.29 (br ⁇ ,3H), 3.41 (br ⁇ ,3H), 3.8 ( ⁇ ,3H), 3.81 ( ⁇ ,3H), 6.8-7.1 (m,3H); N-methoxy-N-methyl-4-chloro-2- methoxybenzamide, NMR 3.29 (br s,3H), 3.4 (br ⁇ ,3H), 3.82 ( ⁇ ,3H), 7.0 (m, IH) , 7.1 (m, IH) , 7.35 (m,lH) ;
  • N-methoxy-N-methyl-2 -methyl ulphonyl-4 - trifluoromethylbenzamide NMR 3.22(s,3H), 3.33(s,3H), 3.75( ⁇ ,3H), 7.81(m,lH), 7.94- 8.09(m,2H) ; N-methoxy-N-methyl-2 -methylthio-4 - trifluoromethylbenzamide, m.p .131-144°C (dec) ,-
  • N-methoxy-N-methyl-2- phenylthiomethylbenzamide NMR3.24 ( ⁇ , 3H) , 3 . 75 ( s , 3H ) , 4 . 51 ( s , 2H) , 7 . 18 - 7 . 44 (m, 8H) , 7 . 89 - 7 . 94 (m, lH ) ;
  • compositions suitable for herbicidal use comprising one or more of the hydroxybenzophenone derivatives of formula I or an agriculturally acceptable salt thereof, in association with, and preferably homogeneously dispersed in, one or more compatible agriculturally- acceptable diluents or carriers and/or surface active agents [i.e. diluents or carriers and/or surface active agents of the type generally accepted in the art as being suitable for use in herbicidal compositions and which are compatible with compounds of formula I] .
  • compositions are used in a broad sense to include not only compositions which are ready for use as herbicides but also concentrates which must be diluted before use.
  • the composition ⁇ contain from 0.05 to 90% by weight of one or more compounds of formula I .
  • the herbicidal compositions may contain both a diluent or carrier and surface-active (e.g. wetting, dispersing, or emulsifying) agent.
  • herbicidal compositions of the present invention may be of the ionic or non-ionic types.
  • the herbicidal compositions according to the present invention may comprise up to 10% by weight, e.g. from 0.05% to 10% by weight, of surface-active agent but, if desired, herbicidal composition ⁇ according to the pre ⁇ ent invention may compri ⁇ e higher proportions of surface-active agent, for example up to 15% by weight in liquid emul ⁇ ifiable suspension concentrates and up to 25% by weight in liquid water soluble concentrates.
  • suitable solid diluents or carriers are aluminium silicate, microfine silicon dioxide, talc, chalk, calcined magnesia, kie ⁇ elguhr, tricalcium pho ⁇ phate, powdered cork, ad ⁇ orbent carbon black and clay ⁇ such as kaolin and bentonite.
  • the solid compo ⁇ ition ⁇ (which may take the form of dust ⁇ , granule ⁇ or wettable powders) are preferably prepared by grinding the compounds of formula I with solid diluents or by impregnating the solid diluents or carriers with solution ⁇ of the compound ⁇ of formula I in volatile solvents, evaporating the solvent ⁇ and, if nece ⁇ ary, grinding the product ⁇ ⁇ o a ⁇ to obtain powders.
  • Granular formulations may be prepared by absorbing the compounds of formula I (dissolved in suitable ⁇ olvent ⁇ , which may, if desired, be volatile) onto the solid diluents or carriers in granular form and, if desired, evaporating the solvent ⁇ , or by granulating compositions in powder form obtained a ⁇ described above.
  • Solid herbicidal compositions, particularly wettable powders and granules may contain wetting or dispersing agents (for example of the types described above) , which may also, when solid, serve as diluents or carriers.
  • Liquid compositions according to the invention may take the form of aqueous, organic or aqueous-organic solution ⁇ , ⁇ u ⁇ pensions and emul ⁇ ion ⁇ which may incorporate a surface-active agent.
  • Surface-active agents which may be pre ⁇ ent in the liquid compo ⁇ itions, may be ionic or non-ionic and may, when liquid, also serve as diluents or carriers.
  • Powders, dispersible granules and liquid compositions in the form of concentrates may be diluted with water or other suitable diluents, for example mineral or vegetable oils, particularly in the case of liquid concentrates in which the diluent or carrier is an oil, to give compositions ready for use.
  • suitable diluents for example mineral or vegetable oils, particularly in the case of liquid concentrates in which the diluent or carrier is an oil, to give compositions ready for use.
  • liquid compositions of the compound of formula I may be used in the form of self -emul ⁇ ifying concentrates containing the active substance ⁇ dissolved in the emulsifying agents or in solvents containing emulsifying agents compatible with the active substances, the simple addition of such concentrates to water producing compositions ready for use.
  • Liquid concentrates in which the diluent or carrier is an oil may be used without further dilution using the electrostatic ⁇ pray technique .
  • Herbicidal compo ⁇ itions according to the present invention may also contain, if de ⁇ ired, conventional adjuvant ⁇ ⁇ uch a ⁇ adhesives, protective colloids, thickeners, penetrating agents, spreading agents, stabiliser ⁇ , ⁇ equestering agents, anti-caking agents, colouring agents and corrosion inhibitors. These adjuvants may also serve as carriers or diluents .
  • Preferred herbicidal composition ⁇ are aqueous suspen ⁇ ion concentrate ⁇ , wettable powder ⁇ , water ⁇ oluble or water dispersible powders, liquid water soluble concentrates, liquid emulsifiable suspension concentrates, water disper ⁇ ible granule ⁇ and emul ⁇ ifiable concentrates.
  • Herbicidal compo ⁇ ition ⁇ may also comprise the compounds of formula I in association with, and preferably homogeneously dispersed in, one or more other pesticidally active compound ⁇ and, if desired, one or more compatible pesticidally acceptable diluents or carriers, surface-active agents and conventional adjuvants as hereinbefore described.
  • Examples of other pesticidally active compounds which may be included in, or used in conjunction with, the herbicidal composition ⁇ of the present invention include herbicides (which are preferred partners), insecticides, fungicides and plant growth regulators .
  • Pe ⁇ ticidally active compound ⁇ and other biologically active materials which may be included in, or used in conjunction with, the herbicidal compositions of the present invention and which are acids, may, if desired, be utilized in the form of conventional derivatives, for example alkali metal and amine salts and esters.
  • herbicidal partners include aclonifen, alachlor, amitrole, atrazine, bentazone, bifenox, bromojcynil, chlortoluron, 2,4-D, dicamba, dichlobenil, dichlorprop, difenzoquat, diflufenican, dithiopyr, dimefuron diuron, ET-751, flampropme hyl , fluometuron, fluoroxypyr, glyphosate and glyphosate trime ⁇ ium (sulfosate) salt, hexazinone, imazapyr, isoproturon, isoxaben, MCPA, mecoprop, metolachlor or alpha- metolachlor, norflurazon, oryzalin, oxadiazon, oxyfluorofen, pendimethalin, ⁇ imazine, ⁇ ulcotrione, ⁇ ulfonyl urea ⁇ ⁇ uch as
  • a suspension concentrate is formed from: Compound 1 20%
  • Similar ⁇ u ⁇ pension concentrates may be prepared by replacing Compound 1 with other hydroxybenzophenone derivatives of formula I .
  • An emulsion concentrate is formed from the following:
  • Synperonic NPE1800 Surfactant
  • Arylan CA Surfactant
  • Solvesso 150 (blending agent) 5.0% Water to 100%
  • NMP N-methylpyrrolidinone
  • a wettable powder is formed from the following:
  • a method for controlling the growth of weeds i.e. undesired vegetation
  • a locu ⁇ which compri ⁇ e ⁇ applying to the locu ⁇ a herbicidally effective amount of at lea ⁇ t one hydroxybenzophenone derivative of formula I or an agriculturally acceptable salt thereof.
  • the hydroxybenzophenone derivatives are normally used in the form of herbicidal compositions (i.e. in association with compatible diluents or carriers and/or surface active agents suitable for use in herbicidal compositions) , for example as hereinafter described.
  • the compounds of formula I show herbicidal activity against dicotyledonous (i.e. broad- leafed) and monocotyledonous (e.g. grass) weeds by pre- and/or post-emergence application.
  • pre-emergence application application to the soil in which the weed seeds or seedlings are present before emergence of the weeds above the surface of the soil .
  • post-emergence application application to the aerial or exposed portions of the weeds which have emerged above the surface of the soil.
  • the compound ⁇ of formula I may be used to control the growth of : broad-leafed weeds, for example, AbutiIon theophrasti, Amaranthus retroflexus, Bidens pilosa, Chenopodium album, Galium aparine, Ipomoea spp ⁇ e.g. Ipomoea purpurea. Sesbania exaltata, Sinapi ⁇ arvensis.
  • Solanum nigrum and Xanthium strumarium, and grass weeds for example Alopecurus mvosuroides , Avena fatua, Digitaria sanguinalis. Echinochloa crus-galli, Eleusine indica and Setaria spp, e.g. Setaria faberii or Setaria viridis, and sedges, for example, Cyperus esculentus.
  • the amounts of compounds of formula I applied vary with the nature of the weeds, the compositions used, the time of application, the climatic and edaphic conditions and (when used to control the growth of weeds in crop-growing areas) the nature of the crops.
  • the rate of application should be sufficient to control the growth of weed ⁇ without cau ⁇ ing ⁇ ub ⁇ tantial permanent damage to the crop.
  • application rates from about 0.01 to about 4.0kg (preferably from 0.01 to 1.0 kg) of active material per hectare give good results.
  • higher or lower application rates may be used, depending upon the particular problem of weed control encountered.
  • the compounds of the invention exhibit herbicidal propertie ⁇ at a dose rate of 250g/ha or lower.
  • the compounds of formula I may be used to control selectively the growth of weeds, for example to control the growth of those specie ⁇ hereinbefore mentioned, by pre- or post- emergence application in a directional or non- directional fashion, e.g. by directional or non- directional spraying, to a locus of weed infe ⁇ tation which is an area used, or to be used, for growing crops, for example cereals, e.g.
  • the compounds of formula I may also be used to control the growth of weeds, especially those indicated above, by pre- or post-emergence application in establi ⁇ hed orchards and other tree-growing areas, for example forests, woods and parks, and plantations, e.g. sugar cane, oil palm and rubber plantations.
  • plantations e.g. sugar cane, oil palm and rubber plantations.
  • they may be applied in a directional or non- directional fashion (e.g. by directional or non- directional spraying) to the weeds or to the soil in which they are expected to appear, before or after planting of the trees or plantations at application rates between 50 g and 5000 g, and preferably between 50 g and 2000 g, most preferably between 100 g and 1000 g of active material per hectare.
  • the compounds of formula I may also be used to control the growth of weeds, especially those indicated above, at loci which are not crop- growing areas but in which the control of weeds is nevertheless desirable.
  • non-crop-growing areas include airfields, industrial sites, railways, roadside verges, the verges of rivers, irrigation and other waterways, scrubland ⁇ and fallow or uncultivated land, in particular where it is desired to control the growth of weeds in order to reduce fire risk ⁇ .
  • the active compounds are normally applied at dosage rates higher than those used in crop-growing areas as hereinbefore described. The precise dosage will depend upon the nature of the vegetation treated and the effect sought.
  • Pre- or post-emergence application, and preferably pre-emergence application, in a directional or non-directional fa ⁇ hion e.g.
  • ⁇ praying at application rate ⁇ between 50 g and 5000 g, and preferably between 50 g and 2000 g, mo ⁇ t preferably between 100 g and 1000 g of active material per hectare are particularly suitable for this purpose.
  • the compounds of formula I When used to control the growth of weeds by pre-emergence application, the compounds of formula I may be incorporated into the soil in which the weeds are expected to emerge. It will be appreciated that when the compounds of formula I are used to control the growth of weeds by post-emergence application, i.e. by application to the aerial or exposed portions of emerged weeds, the compounds of formula I will also normally come into contact with the soil and may also then exercise a pre-emergence control on later-germinating weeds in the ⁇ oil. Where e ⁇ pecially prolonged weed control is required, the application of the compounds of formula I may be repeated if required.
  • the compounds of the invention were applied to the soil surface, containing the seeds, as described in (a) .
  • Pots containing the species represented were allocated to each treatment, with unsprayed controls and controls sprayed with acetone/water alone. After treatment the pots were placed on capillary matting kept in a glass house, and watered by overhead sprinkler (pre- emergence) and sub-irrigation, supplemented overhead (post- emergence) . Visual assessment of weed control and crop damage was made 12 days (post- emergence) and 17 days (pre- emergence) after spraying. The results were expres ⁇ ed a ⁇ the percentage reduction in growth or damage to the crop or weeds, in compari ⁇ on with the plants in the control pots.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
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  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
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Abstract

L'invention concerne des dérivés d'hydroxybenzophénones selon la formule (I). Dans cette dernière, R?1, R2, R3, R4, R5, R6, R7 et R8¿ sont tels que définis dans le descriptif. L'invention traite également de l'utilisation de ces composés comme herbicides.
PCT/EP1997/005210 1996-09-27 1997-09-23 Derives d'hydroxybenzophenones en tant qu'herbicides WO1998013341A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU47051/97A AU4705197A (en) 1996-09-27 1997-09-23 Hydroxybenzophenone derivatives as herbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9620202.3A GB9620202D0 (en) 1996-09-27 1996-09-27 New herbicides
GB9620202.3 1996-09-27

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Publication Number Publication Date
WO1998013341A1 true WO1998013341A1 (fr) 1998-04-02
WO1998013341B1 WO1998013341B1 (fr) 1998-06-18

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AU (1) AU4705197A (fr)
GB (1) GB9620202D0 (fr)
ID (1) ID19545A (fr)
WO (1) WO1998013341A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0967196A2 (fr) * 1998-06-24 1999-12-29 American Cyanamid Company 2-hydroxy substitué benzophénones, leur préparation, leur utilisation comme fongicide et compositions fongiques les contenant
EP1023832A1 (fr) * 1999-01-29 2000-08-02 American Cyanamid Company Suspension aqueuse concentrée

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US3387035A (en) * 1963-11-04 1968-06-04 Air Force Usa Fluorine substituted benzophenone ultraveiolet absorbers
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DE2111766A1 (de) * 1970-03-11 1971-09-30 Ciba Geigy Ag Verwendung von 2-Hydroxybenzophenonen als Stabilisierungsmittel gegen Ultraviolettstrahlung in farbphotographischem Material
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US3387035A (en) * 1963-11-04 1968-06-04 Air Force Usa Fluorine substituted benzophenone ultraveiolet absorbers
DE2033302A1 (de) * 1969-07-25 1971-02-11 Sandoz Ag, Basel (Schweiz) Verfahren zur Herstellung von neuen 2 Hydroxy-3,5 tert butyl-benzophenonen
DE2111766A1 (de) * 1970-03-11 1971-09-30 Ciba Geigy Ag Verwendung von 2-Hydroxybenzophenonen als Stabilisierungsmittel gegen Ultraviolettstrahlung in farbphotographischem Material
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EP0002666A1 (fr) * 1977-11-21 1979-07-11 Hoechst Aktiengesellschaft Acides 1,2-benzisoxazolyloxy (ou thio) acétiques et dérives apparentés, leurs procédés de préparation et médicaments les contenant
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0967196A2 (fr) * 1998-06-24 1999-12-29 American Cyanamid Company 2-hydroxy substitué benzophénones, leur préparation, leur utilisation comme fongicide et compositions fongiques les contenant
EP0967196A3 (fr) * 1998-06-24 2001-12-19 Basf Aktiengesellschaft 2-hydroxy substitué benzophénones, leur préparation, leur utilisation comme fongicide et compositions fongiques les contenant
EP1023832A1 (fr) * 1999-01-29 2000-08-02 American Cyanamid Company Suspension aqueuse concentrée

Also Published As

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ID19545A (id) 1998-07-23
AU4705197A (en) 1998-04-17
GB9620202D0 (en) 1996-11-13

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