GB1601752A - Oxime derivatives and their preparation - Google Patents

Oxime derivatives and their preparation Download PDF

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Publication number
GB1601752A
GB1601752A GB8087/78A GB808778A GB1601752A GB 1601752 A GB1601752 A GB 1601752A GB 8087/78 A GB8087/78 A GB 8087/78A GB 808778 A GB808778 A GB 808778A GB 1601752 A GB1601752 A GB 1601752A
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cooch3
formula
compound
oxime
group
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Novartis AG
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    • 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
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
    • 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
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/02—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by halogen atoms
    • 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
    • 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
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile 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
    • C07D307/56—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 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
    • 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
    • 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
    • C07D333/26—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 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Furan Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Cultivation Of Plants (AREA)

Abstract

Novel compositions which are suitable in agriculture for crop protection contain, together with suitable carrier material, at least one active ingredient from the series comprising oxime ethers, oxime esters or oxime carbamates, the active substance having the formula I <IMAGE> in which the substituents are as defined in Claim 1. The compositions can be used advantageously for crop protection. Such compositions have antidote properties for protecting plants against aggressive agrochemicals and, besides, have other plant-regulating and pesticidal properties.

Description

(54) NOVEL OXIME DERIVATIVES AND THEIR PREPARATION (71) We, CIBA-GEIGY AG, a Swiss Body Corporate, of Basle, Switzerland, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:- This invention relates to novel oxime derivatives and their preparation.
According to the invention there are provided compounds of the general formula I
wherein R1 represents a chlorine atom or a trifluoromethyl or nitro group, R2 represents a hydrogen or chlorine atom or a cyano group, R3 represents a hydrogen atom or a methyl group, R4 represents an amido, methoxycarbonyl, ethoxycarbonyl or cyano group, and X represents a hydrogen or chlorine atom or a cyano or a methyl group.
Preferred are those compounds of the formula I wherein R4 represents a methoxycarbonyl group.
The compounds of the formula I have a plant growth regulating action which in the case of high applied amounts of 6 kg per hectare and more can shift the plant growth regulating action in the direction of a herbicidal action.
The compounds of the formula I may be prepared by processes known per se (Organic Reactions 1953, Vol. 7, pages 343 and 373; Journal f. prakt. Chemie 66, page 353; Liebigs Ann 250, 165) namely by etherifying an oxime of the formula II
(wherein R1, R2 and X are as defined above) or an oxime salt thereof with a halide of the formula III
(wherein R3 and R4 are as defined above and "Hal" represents a halogen, preferably chlorine or bromine, atom).
The etherification of substituted a-oximino compound is effected advantageously with the compounds in the form of their salts, particularly in the form of their alkali metal salts or ammonium salts as is shown in the following selected example
oximealkanecarboxylic acid esters of the formula I (In the above diagram "Hal" denotes halogen, especially Cl or Br).
Suitable as solvents for obtaining the compounds of the formula I are essentially all representatives which behave inertly under the conditions of the reaction. For example, hydrocarbons, particularly however polar solvents, such as acetonitrile, dioxane, "Cellosolve" or DMF, but also ketones, such as methyl ethyl ketone, acetone, etc. Solvents containing hydroxyl groups are excluded.
[Cellosolve is a Registered Trade Mark].
The temperatures are generally in the range of -10"C to about 1500C, preferably between 20 and 1200C.
As agents for splitting off hydrogen halide when a free oxime of formula II is used, it is possible to use bases such as tert. amines (triethylamine, triethylenediamine, piperidine, etc.). Also a suspension of sodium carbonate in the anhydrous reaction medium suffices in some cases.
Oximes are present in two stereoisomeric forms, the syn-form and anti-form.
The compounds of the formula I can be present in either of these forms in the pure state or as mixtures of both. By 'compounds of the formula I' are accordingly meant, within the scope of the present specification, both stereoisomeric forms on their own, or as mixtures with each other in any reciprocal quantitative ratio.
The compounds of the formula I may be prepared by processes analogous to the following although the products of Examples 1 and 2 are not in accordance with the present invention.
Example 1 33.6 g (0.2 mol) of phenylglyoxylonitrile-oxime sodium salt and 25 g (0.22 mol) of chloroacetic acid methyl ester in 200 ml of acetonitrile are held for 3 hours at 6070 C with thorough stirring, in which time the suspension becomes greatly refined. After a further few hours, filtration is performed; the residue is subsequently washed with acetonitrile, and the combined filtrates are concentrated in vacuo to leave an oily residue, which becomes solid after about 24 hours, m.p.
68-700C; Recrystallised from isopropanol: m.p. 71-720C.
Example 2 Production of
a-Cyanobenzylidene-amino-oxacetamide 845 g (5 mols) of benz-acetonitrileoxime as Na salt is suspended in 2.5 litres of acetonitrile, and there is slowly added in the presence of catalytic amounts of Klz with stirring, 468 g (5 mols) of chloroacetamide. The reaction mixture is refluxed for 12 hours; it is then cooled and subsequently allowed to flow into about 12 litres of water. While the salts present are dissolving, the final product precipitates in crystalline form: 882 g (=86.8% of theory), m.p. 128-129 C (from ethanol).
The following compounds were prepared in this manner.
Comp. No. R1 R2 X Q 1 -C1 -C1 -CN -CH2-CO-NH2 2 -Cl -Cl -CN -CH2-OOCH3 4 -Cl -CN -CN -CH2-COOCH3 5 -Cl -CN -CN -CH(CH3)-COOCH3 6 -CF3 -Cl -CN -CH(CH3)-COOCH3 7 -CF3 -Cl -CN -CH2-COOC2H5 8 -NO2 H -CN -CH(CH3)-COOCH3 9 -Cl -Cl -Cl -CH2-CN 10 -Cl -Cl -Cl -CH2-COOCH3 11 -Cl -Cl -Cl -CH(CH3)-COOCH3 12 -Cl -Cl -CH3 -CH2-COOCH3 13 -Cl -Cl -CH3 -CH(CH3)-COOCH3 14 -Cl -Cl H -CH2-COOCH3 15 -Cl -Cl H -CH(CH3)-COOCH3 16 -CF3 -Cl H -CH2-COOCH3 17 -CF3 -Cl H -CH(CH3)-COOCH3
WHAT WE CLAIM IS:1. A compound of the general formula I
wherein R, represents a chlorine atom or a trifluoromethyl or nitro group, R2 represents a hydrogen or chlorine atom or a cyano group, R3 represents a hydrogen atom or a methyl group, R4 represents an amido, methoxycarbonyl, ethoxycarbonyl or cyano group, and X represents a hydrogen or chlorine atom or a cyano or a methyl group.
2. A compound according to Claim 1, wherein R4 represents a methoxycarbonyl group.
3. A compound of the formula
**WARNING** end of DESC field may overlap start of CLMS **.

Claims (7)

  1. **WARNING** start of CLMS field may overlap end of DESC **.
    with stirring, 468 g (5 mols) of chloroacetamide. The reaction mixture is refluxed for 12 hours; it is then cooled and subsequently allowed to flow into about 12 litres of water. While the salts present are dissolving, the final product precipitates in crystalline form: 882 g (=86.8% of theory), m.p. 128-129 C (from ethanol).
    The following compounds were prepared in this manner.
    Comp. No. R1 R2 X Q 1 -C1 -C1 -CN -CH2-CO-NH2 2 -Cl -Cl -CN -CH2-OOCH3 4 -Cl -CN -CN -CH2-COOCH3 5 -Cl -CN -CN -CH(CH3)-COOCH3 6 -CF3 -Cl -CN -CH(CH3)-COOCH3 7 -CF3 -Cl -CN -CH2-COOC2H5 8 -NO2 H -CN -CH(CH3)-COOCH3 9 -Cl -Cl -Cl -CH2-CN 10 -Cl -Cl -Cl -CH2-COOCH3 11 -Cl -Cl -Cl -CH(CH3)-COOCH3 12 -Cl -Cl -CH3 -CH2-COOCH3 13 -Cl -Cl -CH3 -CH(CH3)-COOCH3 14 -Cl -Cl H -CH2-COOCH3 15 -Cl -Cl H -CH(CH3)-COOCH3 16 -CF3 -Cl H -CH2-COOCH3 17 -CF3 -Cl H -CH(CH3)-COOCH3
    WHAT WE CLAIM IS:1. A compound of the general formula I
    wherein R, represents a chlorine atom or a trifluoromethyl or nitro group, R2 represents a hydrogen or chlorine atom or a cyano group, R3 represents a hydrogen atom or a methyl group, R4 represents an amido, methoxycarbonyl, ethoxycarbonyl or cyano group, and X represents a hydrogen or chlorine atom or a cyano or a methyl group.
  2. 2. A compound according to Claim 1, wherein R4 represents a methoxycarbonyl group.
  3. 3. A compound of the formula
  4. 4. A process for preparing a compound of the formula I as claimed in Claim which process comprises etherifying an oxime of the formula II
    (wherein R1, R2 and X are as defined in Claim 1) or an oxime salt thereof with a halide of the formula III
    (wherein R3 and R4 are as defined in Claim 1 and "Hal" represents a halogen atom).
  5. 5. A process according to Claim 4, wherein an alkali metal or ammonium salt of a compound of the formula II is etherified with the halide of the formula III.
  6. 6. A process according to Claim 4 or 5, wherein, in the halide of the formula III, "Hal" represents a chlorine or bromine atom.
  7. 7. A compound according to Claim 1 prepared by the process claimed in any one of Claims 4 to 6.
GB8087/78A 1977-03-02 1978-03-01 Oxime derivatives and their preparation Expired GB1601752A (en)

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CH260677A CH632130A5 (en) 1977-03-02 1977-03-02 Compositions on the basis of oxime ethers, oxime esters or oxime carbamates which are suitable in agriculture for crop protection

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4530716A (en) * 1982-03-15 1985-07-23 Ciba-Geigy Corporation Oxime ethers, compositions containing them and the use thereof
WO2000078710A1 (en) * 1999-06-23 2000-12-28 Alliedsignal Inc. Method of making hydroxylamine salts
US7514439B2 (en) 2005-07-11 2009-04-07 Mitsubishi Tanabe Pharma Corporation Oxime derivative and preparations thereof

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4324579A (en) * 1975-09-11 1982-04-13 Philargo Herbicidal and phytohormonal amidoximes
US4488899A (en) * 1978-08-31 1984-12-18 Ciba-Geigy Corporation Oxime derivatives for protecting plant crops
US4488898A (en) * 1978-08-31 1984-12-18 Ciba-Geigy Corporation Oxime derivatives for protecting plant crops
AT365410B (en) * 1978-08-31 1982-01-11 Ciba Geigy Ag AGENT FOR THE PROTECTION OF CULTIVATED PLANTS FROM AGGRESSIVE VEGETABLES
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US4488900A (en) * 1978-08-31 1984-12-18 Ciba-Geigy Corporation Oxime derivatives for protecting plant crops
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DK93378A (en) 1978-09-03
DD146593A5 (en) 1981-02-18
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ZA781181B (en) 1979-02-28
CS223867B2 (en) 1983-11-25
AT370585B (en) 1983-04-11
BR7801252A (en) 1979-01-02
CA1149398A (en) 1983-07-05
NL7802251A (en) 1978-09-05
NO780714L (en) 1978-09-05
PL205020A1 (en) 1978-11-20
EG13159A (en) 1980-12-31
BE864436A (en) 1978-09-01
TR20211A (en) 1980-10-17
FI780640A (en) 1978-09-03
JPS53108937A (en) 1978-09-22
LU79158A1 (en) 1978-11-27
OA06043A (en) 1981-06-30
FR2387945B1 (en) 1981-11-27
AU3372278A (en) 1979-09-06
AR229079A1 (en) 1983-06-15
ES467450A1 (en) 1978-10-16
ZM3178A1 (en) 1979-02-21
JPS6254096B2 (en) 1987-11-13
ATA145278A (en) 1982-09-15
GR64426B (en) 1980-03-21
AU515449B2 (en) 1981-04-02
IE46471B1 (en) 1983-06-29
MX5502E (en) 1983-09-05
FR2387945A1 (en) 1978-11-17
CH632130A5 (en) 1982-09-30
DD138141A5 (en) 1979-10-17
PL110760B1 (en) 1980-07-31
NZ186597A (en) 1980-10-08
SE7802250L (en) 1978-09-03
BG30612A3 (en) 1981-07-15
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IL54153A0 (en) 1978-04-30
DE2808317A1 (en) 1978-09-07

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PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee

Effective date: 19940301