[go: up one dir, main page]

WO1998003478A1 - Derives de nitrone, procedes et intermediaires pour leur preparation, et leur utilisation comme herbicides - Google Patents

Derives de nitrone, procedes et intermediaires pour leur preparation, et leur utilisation comme herbicides Download PDF

Info

Publication number
WO1998003478A1
WO1998003478A1 PCT/EP1997/003656 EP9703656W WO9803478A1 WO 1998003478 A1 WO1998003478 A1 WO 1998003478A1 EP 9703656 W EP9703656 W EP 9703656W WO 9803478 A1 WO9803478 A1 WO 9803478A1
Authority
WO
WIPO (PCT)
Prior art keywords
optionally substituted
phenyl
formula
groups
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP1997/003656
Other languages
English (en)
Inventor
Charles Walter Ellwood
Aleksei Yakovlevich Tikhonov
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Agriculture Ltd
NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY
Original Assignee
Rhone Poulenc Agriculture Ltd
NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rhone Poulenc Agriculture Ltd, NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY filed Critical Rhone Poulenc Agriculture Ltd
Priority to AU36217/97A priority Critical patent/AU3621797A/en
Publication of WO1998003478A1 publication Critical patent/WO1998003478A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C07D213/20—Quaternary compounds 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
    • 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
    • A01N35/08—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 at least one of the bonds to hetero atoms is to nitrogen
    • A01N35/10—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 at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
    • C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide 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
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/46—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
    • C07C323/47—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom

Definitions

  • This invention relates to novel nitrone derivatives, compositions containing them, processes and intermediates for their preparation, and their use as herbicides.
  • BACKGROUND ART Tikhonov and Volodarskii Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk .
  • Russian patent application number 390073 discloses the preparation of 3-(N- benzylideneamino) -1-phenyl-l-propanone N-oxide as a pharmaceutical intermediate.
  • Japanese patent application number 6,923,322 discloses the preparation of 3-N- (5-nitro-2- furylideneamino) -1- (2-carboxyphenyl) -1-propanone N-oxide useful as an antibiotic or food preservative.
  • the present invention provides nitrone derivatives of formula (I):
  • R 2 represents hydrogen
  • R 3 is selected from hydrogen, R 9 , cycloalkyl containing from three to six carbon atoms, -OR 9 , -S(0) p R 9 and - (CH 2 ) q C0 2 R 9 ; or when R 1 is phenyl optionally substituted by one or more groups R 8 , R 1 and R 3 may be linked together via an ortho-carbon atom of R 1 to form a five or six membered saturated carbocyclic ring which is fused to the phenyl ring;
  • R 4 and R 6 which may be the same or different each represent hydrogen or R 9 ; or when R 1 is phenyl optionally substituted by one or more groups R 8 , R 1 and R 4 may be linked together via an ortho-carbon atom of R 1 to form a five or six membered saturated carbocyclic ring which is fused to the phenyl ring;
  • R 5 represents hydrogen, R 9 or phenyl
  • R 7 represents: phenyl optionally substituted by one or more groups R 8 ; or a heterocyclic ring (generally a 5 or 6- membered heterocyclic ring) containing from one to four heteroatoms in the ring selected from oxygen, nitrogen and sulphur, and which is optionally substituted by one or more groups R 8 ;
  • R 8 represents halogen, R 9 , -C0 2 H, -C0 2 R 9 , -OH, -OR 9 , -S(0) r R 9 , -NRLOR 11 , nitro or cyano;
  • R 9 represents a straight- or branched- chain alkyl group containing from one to six carbon atoms which is optionally substituted by one or more halogen atoms;
  • R 10 and R 11 which may be the same or different, each represent hydrogen or R 9 ;
  • m is zero or one;
  • n, p and r independently are zero, one or two; and
  • q is zero, one or two; a geometric iso er thereof; and agriculturally acceptable salts thereof, which possess valuable herbicidal properties, with the provisos that: (a) when R 1 is phenyl optionally substituted by one or two halogen atoms or a nitro group; or R ⁇ is 4-pyridyl, methyl or tert- butyl; R 4 , R 5 and R 6 are hydrogen and R 7 is phenyl; R 3 is not hydrogen; (b) when R 1 is 2-carboxyphenyl and R 2 , R 3 ,
  • R 4 , R 5 and R 6 are hydrogen; R 7 is not 5-nitro-2- furyl;
  • R 1 when R 1 is phenyl, R 1 and R 3 are linked together via an ortho carbon atom of R 1 to form a six membered saturated carbocyclic ring which is fused to the phenyl ring; and R 2 , R 4 , R 5 and R 6 are hydrogen; R 7 is not phenyl; (d) when R 1 is phenyl optionally substituted by a 4-fluoro atom,- or R 1 is methyl; R 5 and R 6 are hydrogen; R 7 is phenyl; and one of R 3 and R 4 is hydrogen, the other is not methyl; or
  • nitrones of general formula (I) generally exist in the cis (Z) form, in certain cases the trans (E) isomer may be obtained in which the R ⁇ and R 7 groups are transposed.
  • Nitrones of general formula (I) may in certain cases exist in tautomeric forms, shown in general formula (la), (lb) or (Ic) below:
  • compositions containing them and their use as herbicides do form part of the invention.
  • substituents R 1 , R 3 , R 4 , R 5 , R 6 and R 7 contribute to optical isomerism and/or stereo isomerism. 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.
  • alkaline earth metal e.g. calcium and magnesium
  • ammonium and amine e.g. diethanolamine, triethanolamine, octylamine, morpholine and dioctylmethylamine
  • Suitable acid addition salts include salts with inorganic acids, for example hydrochlorides, sulphates, phosphates and nitrates and salts with organic acids for example acetic acid.
  • R represents a heterocyclic ring
  • examples of such rings include the following: thiophene, furan, pyrrole, pyrazine, pyrimidine, pyridazine, thiazole, oxazole, imidazole, pyrazole, isoxazole, isothiazole, oxadiazole, thiadiazole, triazole, pyridine, oxadiazine, thiadiazine, triazine and tetrazole.
  • R 1 is phenyl optionally substituted by from one to five (in particular one or two) groups R 8 are preferred.
  • R 3 represents a straight- or branched- chain alkyl group containing from one to six carbon atoms which is optionally substituted by one or more halogens are preferred.
  • R 8 is preferably halogen, a methyl or ethyl group optionally substituted by one or more halogen atoms, or a methoxy or ethoxy group optionally substituted by one or more halogen atoms .
  • a preferred class of compounds of formula (I) are those wherein: R 1 represents phenyl optionally substituted by one or two R 8 groups, wherein R 8 represents halogen, a methyl or ethyl group optionally substituted by one or more halogen atoms, a methoxy or ethoxy group optionally substituted by one or more halogen atoms, nitro or -S(0) n R 9 wherein R 9 represents methyl or ethyl optionally substituted by one or more halogen atoms; or R 1 represents pyridyl, thienyl or furyl optionally substituted by one or two halogen atoms or optionally halogenated methyl groups,- or R 1 represents straight- or branched- chain alkyl containing from one to three carbon atoms or a benzyl group,-
  • R 3 represents a straight- or branched- chain alkyl group containing from one to four carbon atoms optionally substituted by one or more halogen atoms; methoxy, -S(0)pCH3 or
  • R 4 and R 6 represent hydrogen or methyl
  • R 5 represents hydrogen
  • R 7 represents phenyl optionally substituted by one or two groups R 8 , wherein R 8 represents halogen, nitro, dimethylamino or methoxy,- or R 7 represents pyridyl or thienyl.
  • a further preferred class of compounds of formula (I) are those wherein: R 1 represents phenyl optionally substituted by one or two R 8 groups, wherein R 8 represents halogen, a methyl or ethyl group optionally substituted by one or more halogen atoms, a methoxy or ethoxy group optionally substituted by one or more halogen atoms, or -S(0) n R 9 wherein R 9 represents methyl or ethyl optionally substituted by one or more halogen atoms,- or represents pyridyl or thienyl .
  • R 3 represents a straight- or branched- chain alkyl group containing from one to three carbon atoms ;
  • R 4 , R 5 and R 6 represent hydrogen; and R 7 represents phenyl optionally substituted by one or two groups R 8 , wherein R 8 represents halogen, nitro, dimethylamino or methoxy; or R 7 is pyridyl.
  • R 8 represents halogen, nitro, dimethylamino or methoxy; or R 7 is pyridyl.
  • R 1 represents phenyl optionally substituted by one or two R 8 groups, wherein R 8 represents halogen, a methyl or ethyl group optionally substituted by one or more halogens, a methoxy or ethoxy group optionally substituted by one or more halogen atoms;
  • R 3 represents a straight- or branched- chain alkyl group containing from one to three carbon atoms
  • R 4 , R 5 and R 6 represent hydrogen
  • R 7 represents phenyl which is optionally substituted by one or two groups R 8 , wherein R 8 represents halogen, nitro or dimethylamino; or R 7 is pyridyl .
  • compounds of formula (I) may be prepared by the reaction of a compound of general formula (II) :
  • R 1 , R 2 , R 3 , R 4 and R 5 are as defined above, X represents halogen (preferably chlorine, bromine or iodine) and R 12 , R 13 and R 14 each represent a straight- or branched- chain alkyl group containing from one to six carbon atoms (preferably methyl) , with an oxime of formula (III) or an oxime trimethylsilylether
  • R 6 R 7 R 6 ⁇ R 7 (III) (IV) wherein R 6 and R 7 are as defined above and T S represents the trimethylsilyl group.
  • EP-A- 0423524 describes certain compounds of formula (II) as pharmaceutical intermediates.
  • GB 1097566 and 1097567 describe compounds of formula (II) as anthelmintics .
  • US 3824271 describes compounds of formula (II) as pharmaceutical intermediates. J.R.Dimmock et al., Phar azie, vol 39, pages 467-470, (1984); Arm. Khim. Zh. (1969), vol 22(8), pages 693-701 (CA vol 71, No 25, 123786J); Indian J. Chem. (1973), vol 11(3), pages 214-218; and Tikhonov and Volodarskii, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk. volume 3, pages 144- 147, (1979) also describe certain compounds of formula (II) .
  • compounds of formula (II) in which R 1 represents phenyl optionally substituted by one to five groups R 8 ; R 3 represents ethyl; R 4 and R 5 represent hydrogen; R 8 is selected from halogen, optionally halogenated methyl, optionally halogenated methoxy and -S(0) r CH3. and r represents 0,1 or 2, are novel and as such form a further feature of the present invention.
  • compounds of formula (I) may be prepared by the reaction of a compound of general formula (V) :
  • R 1 , R 2 , R 3 , R 4 and R 5 are as defined above and Y represents a leaving group, for example halo preferably chloro or bromo, with an oxime of formula (III), or an oxime trimethylsilyl ether (IV) above.
  • compounds of formula (I) may be prepared by the reaction of a compound of formula (Va) :
  • reaction of a compound of formula (II) , (V) or (Va) is performed using a compound of formula (III) it is preferably carried out in the presence of a base, e.g. potassium hydroxide in an inert solvent such as 1,4-dioxan and at a temperature from 20°C-60°C.
  • a base e.g. potassium hydroxide in an inert solvent such as 1,4-dioxan
  • the reaction is preferably performed in the absence of base in an inert solvent e.g. tetrahydrofuran and at a temperature from 0°C to 60°C.
  • intermediates (VII) may be converted into the desired compounds of formula (I) either by thermolysis optionally in the presence of a solvent (for example xylene) at a temperature from 100°C-250°C, or alternatively in the presence of an acid
  • compounds of formula (I) may be prepared by the oxidation of a compound of formula (VIII) :
  • compounds of formula (I) may be prepared by the oxidation of N,N-dialkylated hydroxylamines of general formula (IX):
  • compounds of formula (I) in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are defined above may be prepared by the reaction of an N- alkyl hydroxylamine of formula (X) :
  • reaction may be performed in an inert solvent for example an alcohol preferably methanol and at a temperature from 0°C to the reflux temperature of the solvent, generally at ambient temperature .
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 12 and R 13 are as defined above.
  • the reaction is performed in the presence of an alkyl halide R 14 X, wherein R 14 represents an alkyl group preferably methyl, and X represents a halogen atom preferably iodo or bromo, and in an inert solvent for example ether, at 0°C to the reflux temperature of the solvent .
  • Intermediates of formula (X) may be prepared by the reaction of a compound of formula (V) with hydroxylamine .
  • the reaction is preferably performed in an inert solvent for example ethanol and optionally in the presence of a base for example potassium hydroxide and at a temperature from 0°C to 60°C. It is understood that compounds of formula (X) may be prepared by the reaction of a compound of formula (V) with hydroxylamine .
  • the reaction is preferably performed in an inert solvent for example ethanol and optionally in the presence of a base for example potassium hydroxide and at a temperature from 0°C to 60°C. It is understood that compounds of formula (X)
  • (X) may exist in tautomeric equilibrium with the isoxazolidine of formula (Xa) , which when the R 2 , R 3 , R 4 and R 5 values differ may exist in diastereomeric forms:
  • (XII) with borane-pyridine complex or sodium cyanoborohydride in an inert solvent for example ethanol in the presence of an acid preferably hydrochloric acid at a temperature from 0°C to 60°C.
  • the carbonyl group in (XII) may be in a protected form, for example as the ethylene ketal.
  • Intermediates of formula (X) may also be prepared by the reaction of a compound of formula (II) with hydroxylamine in an inert solvent generally an alcohol for example methanol at a temperature from 0°C to 60°C preferably at ambient temperature.
  • an inert solvent generally an alcohol for example methanol at a temperature from 0°C to 60°C preferably at ambient temperature.
  • (XIII) with an aldehyde or ketone of formula R 6 R 7 CO.
  • the reaction is conducted in an inert solvent e.g. toluene in the presence of an acid catalyst preferably 4-toluenesulphonic acid at a temperature from 60°C to the reflux temperature, preferably with removal of the water formed by azeotropic distillation.
  • the carbonyl group in (XIII) may be in a protected form, for example as the ethylene ketal.
  • Intermediates of formula (IX) may be prepared by the reaction of an N- alkylhydroxylamine R 6 R 7 CH-NH-OH, with a compound of formula (V) as defined above, or with a compound of formula (II) as defined above.
  • the reaction is performed in an inert solvent for example ethanol and optionally in the presence of a base for example potassium hydroxide and at a temperature from 0°C to 60°C.
  • reaction is conducted for example in toluene in the presence of an acid catalyst for example 4- toluenesulphonic acid at a temperature from 60°C to the reflux temperature, preferably with removal of the water formed by azeotropic distillation.
  • an acid catalyst for example 4- toluenesulphonic acid at a temperature from 60°C to the reflux temperature, preferably with removal of the water formed by azeotropic distillation.
  • Anti-benzaldoxime (0.63g) was added to a stirred solution of [2- (4-chlorobenzoyl) -but-1- yl] trimethylammonium iodide (2.0g) in a mixture of water and tetrahydrofuran and the resultant mixture treated with potassium hydroxide (0.43g) . The mixture was stirred for 4 hours, diluted with water and then hydrochloric acid (2N) and extracted with ether.
  • Hydrogen chloride gas was passed over the surface of a solution of syn 2-fluoro- benzaldoxime (5.9g) in toluene stirred initially at 80°C under an inert atmosphere. When the temperature of the mixture had fallen to 60°C, the addition of hydrogen chloride was discontinued. The mixture was cooled and the solid filtered off and washed (hexane) . To a suspension of the solid in cold ether was added a cold (0°C) solution of sodium hydroxide (3M) , followed by a cold solution of ammonium chloride. The organic phase was dried (magnesium sulphate) and evaporated to give anti 2-fluorobenzaldoxime (3.56g), m.p. 55°C-60°C. This was shown by NMR to contain 25% of the syn- isomer and was used directly in the next stage.
  • aqueous phase from above was ba ⁇ ified (1 M sodium carbonate solution) , extracted (ether) and the extract dried (magnesium sulphate) to give 1- (2-fluorophenyl) -2- dimethylaminomethyl-1-butanone, used directly in the following stage.
  • a method for controlling the growth of weeds i.e. undesired vegetation at a locus which comprises applying to the locus " a herbicidally effective amount of at least one nitrone derivative of formula I or an agriculturally acceptable salt thereof.
  • the nitrone 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 onocotyledonou ⁇ (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 compounds of formula I may be used to control the growth of: broad-leafed weeds, for example, Abutilon theophrasti, Amaranthus retroflexus, Bidens pilosa, Chenopodiu album. Galium aparine, Ipomoea SPP . e.g. Ipo oea purpurea, Sesbania exaltata. Sinapis arvensis.
  • Solanum nigrum and Xanthium strumarium, and grass weeds for example Alopecurus myosuroides, Avena fatua, Diqitaria 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 compounds of formula I may be used to control selectively the growth of weeds, for example to control the growth of those species 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 infestation which is an area used, or to be used, for growing crops, for example cereals, e.g. wheat, barley, oats, maize and rice, soya beans, field and dwarf beans, peas, lucerne, cotton, peanuts, flax, onions, carrots, cabbage, oilseed rape, sunflower, sugar beet, and permanent or sown grassland before or after sowing of the crop or before or after emergence of the crop.
  • cereals e.g. wheat, barley, oats, maize and rice, soya beans, field and dwarf beans, peas, lucerne, cotton, peanuts, flax, onions, carrots, cabbage, oilseed rape
  • the compounds o "the invention are especially useful for controlling grass weed species.
  • 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 established 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, scrublands and fallow or uncultivated land, in particular where it is desired to control the growth of weeds in order to reduce fire risks.
  • the active compounds When used for such purposes in which a total herbicidal effect is frequently desired, 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.
  • 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 soil. Where especially prolonged weed control is required, the application of the compounds of formula I may be repeated if required.
  • compositions suitable for herbicidal use comprising one or more of the nitrone 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] .
  • the term "homogeneously dispersed" is used to include compositions in which the compounds of formula I are dissolved in other components.
  • 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 compositions 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.
  • Surface-active agents which may be present in 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 compositions according to the present invention may comprise higher proportions of surface-active agent, for example up to 15% by weight in liquid emulsifiable 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, kieselguhr, tricalcium phosphate, powdered cork, adsorbent carbon black and clays such as kaolin and bentonite.
  • the solid compositions (which may take the form of dusts, granules 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 solutions of the compounds of formula I in volatile solvents, evaporating the solvents and, if necessary, grinding the products so as to obtain powders .
  • Granular formulations may be prepared by absorbing the compounds of formula I (dissolved in suitable solvents, which may, if desired, be volatile) onto the solid diluents or carriers in granular form and, if desired, evaporating the solvents, or by granulating compositions in powder form obtained as 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 solutions, suspensions and emulsions which may incorporate a surface-active agent. Surface-active agents, which may be present in the liquid compositions, 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
  • liquid compositions of the compound of formula I may be used in the form of self-emulsifying concentrates containing the active substances 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 spray technique .
  • Herbicidal compositions according to the present invention may also contain, if desired, conventional adjuvants such as adhesives, protective colloids, thickeners, penetrating agents, spreading agents, stabilisers, sequestering agents, anti-caking agents, colouring agents and corrosion inhibitors . These adjuvants may also serve as carriers or diluents .
  • Preferred herbicidal compositions according to the present invention are aqueous suspension concentrates, wettable powders, water soluble or water dispersible powders, liquid water soluble concentrates, liquid emulsifiable suspension concentrates, water dispersible granules and emulsifiable concentrates.
  • Herbicidal compositions according to the present invention may also comprise the compounds of formula I in association with, and preferably homogeneously dispersed in, one or more other pesticidally active compounds and, if desired, one or more compatible pesticidally acceptable diluents or carriers, surface-active agents and conventional adjuvants as hereinbefore described.
  • other pesticidally active compounds which may be included in, or used in conjunction with, the herbicidal compositions of the present invention include herbicides (which are preferred partners) , insecticides and fungicides.
  • Pesticidally active compounds 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.
  • a suspension concentrate is formed from: Nitrone derivative (Compound 1) 20% Ethylan BCP (surfactant) 0.5%
  • Rhodorsil 426R Antifoa ing agent
  • Propylene glycol antifreeze
  • Atagel 50 anti-settling agent 2.0 Water to 100% Similar suspension concentrates may be prepared by replacing Compound 1 with other nitrone derivatives of formula I .
  • Example C2
  • An emulsion concentrate is formed from the following:
  • Nitrone derivative (Compound 1) 10% Synperonic NPE1800 (surfactant) 4.9% Arylan CA (surfactant) 5.0%
  • Solvesso 150 (blending agent) 5.0% Water to 100%
  • NMP N-methylpyrrolidinone
  • a wettable powder is formed from the following:
  • Nitrone derivative (Compound 1) 20.0% Arylan SX flake (surfactant) 3.0% Arkopon T (surfactant) 5.0%
  • Similar wettable powders may be prepared by replacing Compound 1 with other nitrone derivatives of formula I.
  • the compounds of the invention were applied to the soil surface, containing the seeds, as described in (a) .
  • a single pot of each crop and each weed was allocated to each treatment, with unsprayed controls and controls sprayed with acetone alone.
  • the weeds and crops were sown directly into John Innes potting compost in 75 mm deep, 70 mm square pots except for Amaranthus which was pricked out at the seedling stage and transferred to the pots one week before spraying. The plants were then grown in the greenhouse until ready for spraying with the compounds used to treat the plants. The number of plants per pot were as follows : -
  • the compounds used to treat the plants were applied to the plants as described in (a) .
  • a single pot of each crop and weed species was allocated to each treatment, with unsprayed controls and controls sprayed with acetone alone .
  • the seeds were sown in 70 mm square, 75 mm deep plastic pots in non-sterile soil, 3 species per pot .
  • the quantities of seed per pot were as follows : - Weed species Approx no. of seeds/species
  • 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 alone.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (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)
  • Pest Control & Pesticides (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Cette invention se rapporte à des dérivés de nitrone, représentés par la formule (I), où R1 représente: -(CH¿2?)m- (phényle éventuellement substitué par un ou plusieurs groupes R?8¿, qui peuvent être identiques ou différents); or pyridyle, furyle ou thiényle éventuellement substitué par ou plusieurs groupes identiques ou différents R9, -s(O)¿nR?9 et halogène, ou un groupe R9; R2 représente hydrogène; R3 est choisi parmi hydrogène, R9, cylcoalkyle contenant trois à six atomes de carbone, -OR9, -s(O)¿pR?9 and -(CH¿2?)qCO2R?9¿; ou, lorsque R1 représente phényle éventuellement substitué par un ou plusieurs groupes R8, alors R1 et R3 peuvent être liés entre eux par un atome d'ortho-carbone de R1, afin de former un noyau carbocyclique saturé à cinq ou six éléments, qui est fusionné au noyau phényle; R4 et R6, qui peuvent être identiques ou différents, représentent chacun hydrogène ou R9, ou, lorsque R1 représente phényle éventuellement substitué par un ou plusieurs groupes R8, alors R1 et R4 peuvent être liés entre eux par un atome d'ortho-carbone de R1, afin de former un noyau carbocyclique saturé à cinq ou six éléments, qui est fusionné au noyau phényle; R5 représente hydrogène, R9 ou phényle; R7 représente: phényle éventuellement substitué par un ou plusieurs groupes R8; ou un noyau hétérocyclique contenant un à quatre hétéroatomes dans le noyau, choisis parmi oxygène, azote et soufre, et qui est éventuellement substitué un ou plusieurs groupes R8; R8 représente halogène, R9, -CO2H, -CO2R9, -OH, -OR9, -S(O)¿r?R?9, -NR10R11¿, nitro et cyano; R9 représente un groupe alkyle à chaîne droite ou ramifiée contenant un à six atomes de carbone que est éventuellement substitué par un ou plusieurs halogènes; R?10 et R11¿ qui peuvent être identiques ou différents, représentent chacun hydrogène ou R9; m est égal à zéro ou à un; n, p et r sont chacuns égaux séparement à zéro, à un ou à deux; et q est égal à un ou à deux. Cette invention se rapporte également à un isomère géométrique de ces composés; ou à un sel de ces composés qui soit acceptable en agriculture; cette invention se rapportant également à l'utilisation de ces composés comme herbicides.
PCT/EP1997/003656 1996-07-18 1997-07-10 Derives de nitrone, procedes et intermediaires pour leur preparation, et leur utilisation comme herbicides Ceased WO1998003478A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU36217/97A AU3621797A (en) 1996-07-18 1997-07-10 Nitrone derivatives, processes and intermediates for their preparation, and their use as herbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
PCT/GB1996/001738 WO1998003479A1 (fr) 1996-07-18 1996-07-18 Derives de nitrones, procedes et intermediaires de preparation, et utilisation comme herbicides
GBPCT/GB96/01738 1996-07-18

Publications (1)

Publication Number Publication Date
WO1998003478A1 true WO1998003478A1 (fr) 1998-01-29

Family

ID=10787730

Family Applications (2)

Application Number Title Priority Date Filing Date
PCT/GB1996/001738 Ceased WO1998003479A1 (fr) 1996-07-18 1996-07-18 Derives de nitrones, procedes et intermediaires de preparation, et utilisation comme herbicides
PCT/EP1997/003656 Ceased WO1998003478A1 (fr) 1996-07-18 1997-07-10 Derives de nitrone, procedes et intermediaires pour leur preparation, et leur utilisation comme herbicides

Family Applications Before (1)

Application Number Title Priority Date Filing Date
PCT/GB1996/001738 Ceased WO1998003479A1 (fr) 1996-07-18 1996-07-18 Derives de nitrones, procedes et intermediaires de preparation, et utilisation comme herbicides

Country Status (2)

Country Link
AU (1) AU3621797A (fr)
WO (2) WO1998003479A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI562979B (en) * 2015-08-06 2016-12-21 Nat Univ Chung Cheng Method of manufacturing nitrone compounds

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6912529B1 (en) * 1998-04-01 2005-06-28 Multex Systems, Inc. Method and system for storing and retrieving documents

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3740441A (en) * 1971-05-03 1973-06-19 Scm Corp Alpha-aryl-n-lower alkyl nitronecontaining compositions useful as anti-microbial agents
US5110831A (en) * 1990-11-30 1992-05-05 Du Pont Merck Pharmaceutical Company Vinylogous hydroxamic acids and derivatives thereof as 5-lipoxygenase inhibitors

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3740441A (en) * 1971-05-03 1973-06-19 Scm Corp Alpha-aryl-n-lower alkyl nitronecontaining compositions useful as anti-microbial agents
US5110831A (en) * 1990-11-30 1992-05-05 Du Pont Merck Pharmaceutical Company Vinylogous hydroxamic acids and derivatives thereof as 5-lipoxygenase inhibitors

Non-Patent Citations (33)

* Cited by examiner, † Cited by third party
Title
A. ALLAIS, BULL. SOC. CHIM. FRANCE, 1949, pages 536 - 538, XP000644514 *
A. BELLY ET AL, BULL. SOC. CHIM. FR., 1972, pages 3951 - 3954 *
A. PADWA ET AL, J. AM. CHEM. SOC., vol. 89, no. 1, 1967, pages 102 - 112, XP002048856 *
A. YU. TIKHONOV ET AL, SIB. KHIM. ZH., no. 2, 1993, pages 97 - 104 *
A.YA. TIKHONOV ET AL, IZV. AKAD. NAUK SSSR, SER. KHIM., no. 10, 1973, pages 2372 - 2373 *
A.YA. TIKHONOV ET AL, IZV. SIB. OTD. AKAD. NAUK SSSR, SER. KHIM. NAUK, no. 3, 1979, pages 144 - 147 *
A.YA. TIKHONOV ET AL, KHIM. GETEROTSIKL. SOEDIN., no. 4, 1981, pages 526 - 529 *
A.YA. TIKHONOV ET AL, ZH. ORG. KHIM., vol. 9, no. 4, 1973, pages 770 - 775 *
CHEMICAL ABSTRACTS, vol. 106, no. 15, 13 April 1987, Columbus, Ohio, US; abstract no. 119393, XP002048862 *
CHEMICAL ABSTRACTS, vol. 118, no. 25, 21 June 1993, Columbus, Ohio, US; abstract no. 254798b, XP002048863 *
CHEMICAL ABSTRACTS, vol. 119, no. 19, 8 November 1993, Columbus, Ohio, US; abstract no. 203386d, XP002048860 *
CHEMICAL ABSTRACTS, vol. 52, no. 14, 25 July 1958, Columbus, Ohio, US; abstract no. 11860d, XP002048857 *
CHEMICAL ABSTRACTS, vol. 56, no. 9, 30 April 1962, Columbus, Ohio, US; abstract no. 10301a, XP002048859 *
CHEMICAL ABSTRACTS, vol. 72, no. 15, 13 April 1970, Columbus, Ohio, US; abstract no. 78850, XP002029891 *
CHEMICAL ABSTRACTS, vol. 79, no. 3, 23 July 1973, Columbus, Ohio, US; abstract no. 18284, XP002029889 *
CHEMICAL ABSTRACTS, vol. 80, no. 9, 4 March 1974, Columbus, Ohio, US; abstract no. 47888, XP002029892 *
CHEMICAL ABSTRACTS, vol. 83, no. 1, 7 July 1975, Columbus, Ohio, US; abstract no. 9871f, XP002048861 *
CHEMICAL ABSTRACTS, vol. 91, no. 19, 5 November 1979, Columbus, Ohio, US; abstract no. 157364, XP002029888 *
CHEMICAL ABSTRACTS, vol. 95, no. 9, 31 August 1981, Columbus, Ohio, US; abstract no. 80878, XP002029890 *
CHEMICAL ABSTRACTS, vol. 96, no. 11, 15 March 1982, Columbus, Ohio, US; abstract no. 85501u, XP002048858 *
DATABASE BEILSTEIN BEILSTEIN INFORMATIONSSYSTEME GMBH; XP002048864 *
DATABASE BEILSTEIN BEILSTEIN INFORMATIONSSYSTEME GMBH; XP002048865 *
F. ASINGER ET AL, MONATSH. CHEM., vol. 88, 1957, pages 464 - 477 *
F.J. MCEVOY ET AL, J. ORG. CHEM., vol. 38, no. 23, 1973, pages 4044 - 4048, XP000644508 *
H.O. HOUSE ET AL, J. ORG. CHEM., vol. 43, no. 22, 1978, pages 4316 - 4323, XP000644511 *
K. GOERLITZER ET AL, ARCH. PHARM. (WEINHEIM, GER.), vol. 314, no. 11, 1981, pages 938 - 949 *
K.N. ZELENIN ET AL, CHEM. HETEROCYCL. COMPD. (ENGL. TRANSLAT.), vol. 26, no. 11, 1990, pages 1301 - 1304 *
M. VENUGOPAL ET AL, PROC. - INDIAN ACAD. SCI., CHEM. SCI., vol. 105, no. 1, 1993, pages 19 - 23 *
S.B. LOHIYA ET AL, INDIAN J. CHEM., SECT. B, vol. 25B, no. 3, 1986, pages 279 - 282 *
S.W. WRIGHT ET AL, BIOORG. MED. CHEM. LETT., vol. 2, no. 9, 1992, pages 1079 - 1084, XP000197002 *
S.W. WRIGHT ET AL, J. MED. CHEM., vol. 35, no. 22, 1992, pages 4061 - 4068, XP000644426 *
T. UEDA, NIPPON KAGAKU ZASSHI, vol. 81, 1960, pages 1751 - 1756 *
V.I. ESAFOV ET AL, IZV. VYSSH. UCHEBN. ZAVED., KHIM. KHIM. TEKHNOL., vol. 18, no. 1, 1975, pages 148 - 150 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI562979B (en) * 2015-08-06 2016-12-21 Nat Univ Chung Cheng Method of manufacturing nitrone compounds
US9708242B2 (en) 2015-08-06 2017-07-18 National Chung Cheng University Method of manufacturing nitrone compound

Also Published As

Publication number Publication date
AU3621797A (en) 1998-02-10
WO1998003479A1 (fr) 1998-01-29

Similar Documents

Publication Publication Date Title
DE69431576T2 (de) Isoxazole Derivate und ihre Verwendung als Herbizide
EP0527036B1 (fr) Dérivés de 4-benzoylisoxazole et leur utilisation comme herbicides
DE69231510T2 (de) Isoxazolderivate als Herbizide
EP0470856B1 (fr) Dérivés d'isoxazole, procédés pour leur fabrication et leurs applications comme herbicides
EP0634413A1 (fr) Herbicides
AU666397B2 (en) 4-heteroaroylisoxazole derivatives which are useful as herbicides
US5849928A (en) Herbicidal isoxazole and 2-cyano-1,3-dione compounds
IE921155A1 (en) New herbicides
WO1995025099A1 (fr) Derives de 2-cyano-1,3-dione utiles en tant qu'herbicides
AU658044B2 (en) New herbicides
US4302238A (en) Herbicidal isoxazolidine-3,5-diones
WO1995031446A1 (fr) Derives de 4-benzoylisoxazole et leur utilisation comme herbicides
WO1998003478A1 (fr) Derives de nitrone, procedes et intermediaires pour leur preparation, et leur utilisation comme herbicides
WO1994004530A1 (fr) Quinolinyl oxadiazoles herbicides
US5721193A (en) 2-oximinomethyl-1-phenyl-1,3-propanedione derivatives as herbicides
AU716198B2 (en) 1,3-oxazin-4-one derivatives as herbicides
US5393730A (en) Nicotinic acid hydrazone compounds which have useful herbicidal compositions
GB2327418A (en) Derivatives of 2-benzoylcyclohexane-1,3-dione
WO1995025105A1 (fr) Derives d'isoxazole et leur utilisation en tant qu'herbicides
WO2025052333A1 (fr) Nouveaux composés 1,2,4-oxadiazoles utilisés comme fongicide
HK1003790B (en) 4-benzoylisoxazole derivatives and their use as herbicides

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AL AU BA BB BG BR CA CN CU CZ EE GE HU IL IS JP KP KR LK LR LT LV MG MK MN MX NO NZ PL RO SG SI SK SL TR TT UA US UZ VN YU AM AZ BY KG KZ MD RU TJ TM

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH KE LS MW SD SZ UG ZW AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: CA

NENP Non-entry into the national phase

Ref country code: JP

Ref document number: 1998506495

Format of ref document f/p: F

122 Ep: pct application non-entry in european phase