Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
  • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
  • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
  • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
• • 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
  • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
  • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
• • 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
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
  • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
• • 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
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
  • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• • 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
  • C07C323/01—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 halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
  • C07C323/09—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 halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
  • C07C39/24—Halogenated derivatives
  • C07C39/367—Halogenated derivatives polycyclic non-condensed, containing only six-membered aromatic rings as cyclic parts, e.g. halogenated poly-hydroxyphenylalkanes
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
  • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
  • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
  • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
  • C07D235/26—Oxygen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
  • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
  • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
  • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
  • C07D235/30—Nitrogen atoms not forming part of a nitro radical
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
  • C07D277/62—Benzothiazoles
  • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
  • C07D277/62—Benzothiazoles
  • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
  • C07D277/82—Nitrogen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
  • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

• the invention relates to new substituted biphenyls, to their production and to intermediate products for their production and to their use as herbicides.
• acetamidobiphenyl compounds have herbicidal properties (WO 93/11097). Frequently, however, the herbicidal action of the known compounds is insufficient, or there is a suitable herbicidal action but selectivity problems arise in principal agricultural crops.
• X is oxygen, sulphur, >NH, >NCH 3 , >NCHO, >NCOCH 3 , >NSO 2 CH 3 or >NCOCF 3
• Y is oxygen, sulphur, >NH, >NCH 3 , >NC 2 H 5 , >NCHO, >NSO 2 CH 3 ,
• R 1 is hydrogen, C 1 -C 4 alkyl, C 1 -C 2 alkoxy, phenyl-C 1 -C 2 alkoxy, hydroxy-C 1 -C 2 alkyl, C 1 -C 2 -alkoxy-C 1 -C 2 alkyl, halo-C 1 -C 2 alkyl, halo-C 1 -C 4 alkoxy, C 1 -C 2 alkylthio,
• R 7 is hydrogen, C 1 -C 3 alkyl or halo-C 1 -C 3 alkyl
• R 8 R 9 are the same or different and are hydrogen, C 1 -C 3 alkyl or
• R 10 is hydrogen, C 1 -C 3 alkyl, halo-C 1 -C 3 alkyl or phenyl,
• R 2 is C 1 -C 4 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, halogen, C 1 -C 3 haloalkylthio, C 1 -C 3 alkylthio, cyano or nitro,
• halogen encompasses fluorine, chlorine, bromine and iodine.
• alkyl includes cases where the carbon chain can be branched or unbranched.
• R , R , n and X have the meaning given in general formula I, optionally in the presence of a base and of a solvent, with a benzo-condensed heterocycle of general formula III
• Y , R 3 , R 4 , R 5 and R 6 have the meaning given in general formula I and Z stands for a leaving group such as e . g . Cl , Br , I , -SO 2 alkyl or -SO 2 -aryl , or b ) by reacting a compound of general formula IV
• R 1 , n, X, Y, R , R 4 , R 5 and R 6 have the meaning given in general formula I and U stands for bromine, iodine or -O-SO 2 -CF 3 , with a compound of general formula VII
• R 2 has the meaning given in general formula I and V stands for Li, MgCl, MgBr, B(OH) 2 or trialkyl tin, in the presence of a catalyst.
• the subject-matter of the invention are also compounds of general formulae Ila and lIb
• R 1 and n have the meaning given in formula I and U stands for bromine, iodine or -O-SO 2 CF 3 , with a compound of general formula IX
• R 2 has the meaning given in formula I and V stands for Li, MgCl, MgBr, B(OH) 2 or trialkyl tin, in the presence of a catalyst.
• the intermediate products of general formula lIb can be produced for example ii) by reacting an aniline of general formula X
• R 1 , R 2 and n have the meaning given in general formula I, according to methods customary in the literature.
• acetonitrile, dimethyl formamide and dimethyl sulphoxide are suitable in particular as solvents.
• Tertiary amines such as e.g. pyridines, alkali or alkaline earth carbonates or hydrogen carbonates, alkaline earth oxides or sodium or potassium hydride can be used as bases.
• the compounds according to the invention are processed in the usual manner. Purification takes place e.g. by crystallization or column chromatography.
• the compounds according the invention are colourless or slightly yellow-coloured crystalline or viscous substances, some of which are readily soluble in chlorinated hydrocarbons, such as for example methylene chloride or chloroform, ethers, such as for example diethyl ether or tetrahydrofuran, alcohols, such as for example methanol or ethanol, ketones, such as for example acetone or butanone, amides, such as for example dimethyl formamide, or also sulphoxides, such as for example dimethyl sulphoxide.
• chlorinated hydrocarbons such as for example methylene chloride or chloroform
• ethers such as for example diethyl ether or tetrahydrofuran
• alcohols such as for example methanol or ethanol
• ketones such as for example acetone or butanone
• amides such as for example dimethyl formamide
• sulphoxides such as for example dimethyl sulphoxide.
• the active ingredients according to the invention show a good herbicidal action in the case of broad-leaved weeds and grasses.
• Selective use of the active ingredients according to the invention is possible in various crops, e.g. in rapeseed, beet, soyabeans, cotton, rice, maize, barley, wheat and other types of cereal.
• individual analogous active ingredients are also particularly suitable as selective herbicides in beet, cotton, soya, maize and cereals.
• the compounds can also be used for weed control in perennial crops, such as e.g in forest, ornamental tree and shrub, fruit, wine, citrus, nut, banana, coffee, tea, rubber, palm oil, cocoa, berried fruit and hop plantations.
• the active ingredients according to the invention can be used e.g. with the following genera of plants:
• the application quantities fluctuate, depending on the type of application pre- and post-emergence, between 0.001 to 5 kg/ha.
• the active ingredients according to the invention can also be used as a defoliant, a desiccant and as a haulm destroyer.
• Suitable as preparation forms are e.g. emulsion concentrates, suspensions and salts. The addition of higher proportions of wetting agent is advantageous in appropriate cases.
• the action intensity and the speed of action can for example be promoted by action-enhancing additives, such as organic solvents, wetting agents and oils.
• action-enhancing additives such as organic solvents, wetting agents and oils.
• the active ingredients according to the invention or their mixtures are used expediently in the form of preparations, such as powders, scattering preparations, granulates, solutions, emulsions or suspensions, with the addition of liquid and/or solid carrier substances and diluents and optionally adhesives, wetting agents, emulsification and/or dispersion auxiliaries.
• Suitable liquid carrier substances are for example aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethyl sulphoxide, dimethyl formamide, also mineral oil fractions and vegetable oils.
• Suitable as solid carrier substances are minerals, such as for example bentonite, silica gel, talc, kaolin, attapulgite, limestone and vegetable products, such as for example powders.
• Surface-active substances that may be cited are for example calcium lignin sulphonate, polyethylene alkylphenyl ether, naphthalene sulphonic acids and their salts, phenol sulphonic acids and their salts, formaldehyde condensates, fatty alcohol sulphates and substituted benzene sulphonic acids and their salts.
• the proportion of the active ingredient(s) in the various preparations can vary within wide limits.
• the agents contain about 10 to 90 percent by weight active ingredient, about 90 to 10 percent by weight liquid or solid carrier substances and optionally up to 20 percent by weight surface-active substances.
• the agents can be applied in the usual manner, for example with water as carrier in spray-mix quantities of about 100 to 1000 litres/ha. Using the agents in so-called low-volume and ultra-low processes is also possible, as is their application in the form of so-called microgranulates.
• preparations can be produced in ways known per se, for example by grinding or mixing processes. If desired, preparations of the individual components can also be mixed just prior to their use, as is carried out in practice for example in the so- called tank-mix process.
• the reaction mixture is poured onto 50 ml iced water and extracted three times with 200 ml diethylether in each case.
• the combined organic phases are washed once with 200 ml of 1 % sodium hydroxide solution and twice with 200 ml water in each case, dried over magnesium sulphate, filtered and concentrated on a rotary evaporator.
• the residue is dissolved in 30 ml diethyl ether and mixed under reflux with 9.29 g (166 mol) potassium hydroxide.
• the mixture is then boiled under reflux for 18 hours.
• the reaction mixture is then acidified with 1 molar sulphuric acid and extracted four times with 50 ml diethyl ether in each case.
• the combined organic phases are washed twice with 100 ml water in each case, dried over magnesium sulphate, filtered and concentrated.
• GALAP Galium aparine 3 75 - 89 % damage
• IPOSS Ipomoea purpurea 4 90 - 100 % damage
• the plant species listed were treated in a green house after emergence with the compounds listed in the given application quantity of active ingredient/ha. For this purpose the compounds were sprayed uniformly over the plants as an emulsion with 500 litres water/ha. Three weeks after the treatment the compounds according to the invention displayed a high cultivated plant selectivity in wheat and maize with excellent action against weeds.
• the compounds listed in the table were applied by pipetting onto a water surface area of approx. 170 cm 2 in a green house, the test plants being used in the pre-emergence phase and in the 1-2 leaf phase.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• 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)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

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Citations (6)

• 1995
  • 1995-08-15 IL IL11495095A patent/IL114950A0/xx unknown
  • 1995-08-18 AU AU33468/95A patent/AU3346895A/en not_active Abandoned
  • 1995-08-18 WO PCT/EP1995/003285 patent/WO1996006089A1/en active Application Filing
  • 1995-08-22 TR TR95/01046A patent/TR199501046A1/tr unknown
  • 1995-09-19 TW TW084109824A patent/TW281623B/zh active

Patent Citations (6)

Non-Patent Citations (15)

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