EP0039168A1 - Amidoximether insecticides - Google Patents

Amidoximether insecticides Download PDF

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Publication number
EP0039168A1
EP0039168A1 EP81301623A EP81301623A EP0039168A1 EP 0039168 A1 EP0039168 A1 EP 0039168A1 EP 81301623 A EP81301623 A EP 81301623A EP 81301623 A EP81301623 A EP 81301623A EP 0039168 A1 EP0039168 A1 EP 0039168A1
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EP
European Patent Office
Prior art keywords
compound
formula
alkyl
mole
insecticidal
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.)
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EP81301623A
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German (de)
French (fr)
Inventor
Jill Helaine Paul
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 CropScience Inc USA
Original Assignee
Rhone Poulenc Industries SA
Rhone Poulenc Inc
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Publication of EP0039168A1 publication Critical patent/EP0039168A1/en
Withdrawn legal-status Critical Current

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    • 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
    • C07C259/12—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 nitrogen atoms, e.g. N-hydroxyamidines
    • C07C259/18—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 nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • A01N41/10—Sulfones; Sulfoxides
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom

Definitions

  • This invention relates to certain aryl amidoxime ethers of 3-phenoxybenzyl alcohol, which have insecticidal activity.
  • the present invention provides a compound having the formula: wherein R is halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyl, C 1 -C 6 alkylthio, C 1 -C 6 haloalkyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, C 1 -C 6 alkylamino, cyano, nitro, C 1 -C 6 carboalkoxy, C 1 -C 6 alkylsulphonyl, C l -C 6 alkox y C 1 -C 6 alkyl, C 2 -C 6 haloalkenyl or C l -C 6 acyl, n is 0 to 5, R 1 and R are hydrogen, C 1 -C 6 alkyl, C3-C 6 cycloalkyl, C 1 -C 6 alkylcycloalky
  • the present invention also provides an insecticidal composition
  • an insecticidal composition comprising a carrier and an insecticidal amount of a compound as described above.
  • the present invention further provides a method of combatting insects which comprises contacting them with an insecticidal amount of a compound as described above.
  • step (A) i.e., benzaldehyde and substituted benzaldehydes, are obtained from commercial sources.
  • the benzaldehydes were dissolved in methanol and refluxed 3-5 hours in the presence of an excess of hydroxylamine hydrochloride and sodium acetate in H 2 0.
  • the reaction mixture was quenched with H 2 0 and the oxime was extracted into an organic solvent. Recrystallization from either hexane, hexane/CHCl 3 or EtOH/H 2 O followed.
  • p-Chlorophenyl hydroxamoyl chloride (0.7 g., 0.0037 mole) was dissolved in 20 ml. of diethyl ether.
  • One milliliter (0.011 mole) of isopropylamine in 10 ml. of diethyl ether was added dropwise, immediately causing precipitation of isopropylamine hydrochloride.
  • the reaction mixture was stirred at room temperature for 2 hours, followed by quenching with 50 ml. H 2 0.
  • the layers were separated and the aqueous layer was extracted once with diethyl ether.
  • the combined organic extracts were washed twice with water, dried, and evaporated to yield 0.6 g. (0.0028 mole) of product.
  • a solution of 0.02 mole of amidoxime in 20 ml. of ethanol is added to a freshly prepared ethanolic solution of 0.02 mole N aOEt.
  • the mixture is stirred at room temperature for 30 minutes and concentrated under reduced pressure to dryness.
  • the resulting sodium oximate salt is dissolved in a minimum volume of 90% DMF and 1 0 % t-butanol, whereupon 0.02 mole of 3-phenoxybenzyl bromide is added dropwise, causing an exotherm of ⁇ 8°.
  • the reaction mixture is stirred overnight at room temperature and poured into H 2 0.
  • the resulting oil is extracted two times into toluene.
  • the combined organic layers are washed with 5% NaOH (50:50 H 2 0/ethanol), H 2 0, dried over M G SO 4 and concentrated under reduced pressure to yield 0.15-0.19 mole of > 90% pure product.
  • the compounds of this invention have been found to exhibit considerable biological activity. They are especially potent pesticides when used to control or combat important agricultural pests. These compounds can be used in various ways to achieve biological action. 'They can be applied per se, as solids or in vaporized form, but are preferably applied as the toxic components in pesticidal compositions of the compound and a carrier.
  • the compositions can be applied as dusts, as liquid sprays, or as gas-propelled sprays and can contain, in addition to a carrier, additives such as emulsifying agents, wetting agents, binding agents, gases compressed to the liquid state, odorants and stabilizers.
  • additives such as emulsifying agents, wetting agents, binding agents, gases compressed to the liquid state, odorants and stabilizers.
  • a wide variety of liquid and solid carriers can be used in the pesticidal compositions.
  • liquid carriers examples include water, organic solvents such as alcohols, ketones, amides, and esters, mineral oils such as kerosene, light oils, and medium oils, and vegetable oils such as cottonseed oil.
  • solid carriers include talc, bentonite, diatomaceous earth, pyrophyllite, fullers earth, gypsum, flours derived from cottonseeds and nut shells, and various natural and synthetic clays having a pH not exceeding about 9.5.
  • the amount of the compounds of this invention utilized in pesticidal compositions will vary rather widely. It depends to some extent upon the type of composition in which the material is being used, the nature of the condition to be controlled, and the method of application (e.i., spraying, dusting, etc.). In the ultimate pesticidal composition, as applied in the field, pesticide concentrations as low as 0.0001 weight percent of the total composition can be used. In general, compositions, as applied, containing 0.05 weight percent pesticide in either liquid or solid carrier, give excellent results. In some cases, however, stronger dosages up to 10 weight percent may be required.
  • pesticidal compositions are usually prepared in the form of concentrates, which are diluted in the field to the concentration desired for application.
  • the concentrate can be a wettable powder containing large amounts of the compound of this invention, a carrier (e.g., attapulgite or other clay), and wetting and dispersing agents.
  • a carrier e.g., attapulgite or other clay
  • Such powders can be diluted prior to application, by dispersing it in water to obtain a sprayable suspension containing the concentration of pesticide desired for application.
  • Other concentrates can be solutions that can be later diluted, e.g., with kerosene.
  • the contemplated pesticidal compositions contain between 0.0001 percent and about 8 0 percent, by weight of the compositions, of a pesticidal compound of this invention and a carrier, liquid or solid, as defined hereinbefore.
  • One milliliter of an aqueous solution or suspension of the candidate compound is pipetted into a 9 cm. petri dish containing filter paper and 0.1 gm. granular sugar. Ten adults are admitted and the dish is closed.
  • Lima bean leaves of a uniform size are momentarily dipped in a 5 0 0 ppm. water-acetone of the test material. Treated leaves are placed on moistened filter paper in 9 cm. petri dishes and allowed to air dry, and then are infested. The dishes are then closed.
  • Examples 1 to 8 were subjected to the aforedescribed insecticide tests. Test concentrations and results are set forth in the Table.

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  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (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)

Abstract

This invention discloses certain aryl amidoxime ethers of 3-phenoxybenzyl alcohol, which have insecticidal activity.

Description

  • This invention relates to certain aryl amidoxime ethers of 3-phenoxybenzyl alcohol, which have insecticidal activity.
  • The present invention provides a compound having the formula:
    Figure imgb0001
    wherein R is halogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C1-C6 alkylthio, C1-C6 haloalkyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, C1-C6 alkylamino, cyano, nitro, C1-C6 carboalkoxy, C1-C6 alkylsulphonyl, Cl-C6 alkoxy C1-C6 alkyl, C2-C6 haloalkenyl or Cl-C6 acyl, n is 0 to 5, R1 and R are hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkylcycloalkyl (C3-C6), or C2-C6 alkenyl.
  • The present invention also provides an insecticidal composition comprising a carrier and an insecticidal amount of a compound as described above.
  • The present invention further provides a method of combatting insects which comprises contacting them with an insecticidal amount of a compound as described above.
  • In Japanese Patent No. 154,426, there are disclosed pyrethroid alcohol esters of substituted phenyl- a-dimethylaminoacetic acid having insecticidal activity.
  • Examples of the compounds of this invention are:
    Figure imgb0002
    Figure imgb0003
  • The compounds of this invention are prepared in accordance with the following series of steps:
    Figure imgb0004
    Figure imgb0005
    Figure imgb0006
    Figure imgb0007
  • The ArCHO reactants in step (A), i.e., benzaldehyde and substituted benzaldehydes, are obtained from commercial sources.
    • General Procedure A for Benzaldoximes
  • In general, the benzaldehydes were dissolved in methanol and refluxed 3-5 hours in the presence of an excess of hydroxylamine hydrochloride and sodium acetate in H20. The reaction mixture was quenched with H20 and the oxime was extracted into an organic solvent. Recrystallization from either hexane, hexane/CHCl3 or EtOH/H2O followed.
    • General Procedure B for Aryl Hydroxamoyl Chlorides
  • A solution of p-chlorobenzaldoxime (1.0 g., 0.0065 mole) in 20 ml. chloroform was cooled to -5°C. Gaseous chlorine was bubbled through the solution at such a rate as to maintain the temperature below 0°C. (-10 to 0°C.). Chlorine addition was stopped after the solution changed from colorless to blue to green. Minor amounts of solids were filtered and washed with chloroform. The filtrate was evaporated under reduced pressure to yield 0.7 g. (0.0037 mole) of product as an off-white solid (m.p. 86-87°C.).
    • General Procedure C for Aryl Amidoximes
  • p-Chlorophenyl hydroxamoyl chloride (0.7 g., 0.0037 mole) was dissolved in 20 ml. of diethyl ether. One milliliter (0.011 mole) of isopropylamine in 10 ml. of diethyl ether was added dropwise, immediately causing precipitation of isopropylamine hydrochloride. The reaction mixture was stirred at room temperature for 2 hours, followed by quenching with 50 ml. H20. The layers were separated and the aqueous layer was extracted once with diethyl ether. The combined organic extracts were washed twice with water, dried, and evaporated to yield 0.6 g. (0.0028 mole) of product.
    • General Procedure D for Amidoximethers
  • A solution of 0.02 mole of amidoxime in 20 ml. of ethanol is added to a freshly prepared ethanolic solution of 0.02 mole NaOEt. The mixture is stirred at room temperature for 30 minutes and concentrated under reduced pressure to dryness. The resulting sodium oximate salt is dissolved in a minimum volume of 90% DMF and 10% t-butanol, whereupon 0.02 mole of 3-phenoxybenzyl bromide is added dropwise, causing an exotherm of ~8°. The reaction mixture is stirred overnight at room temperature and poured into H20. The resulting oil is extracted two times into toluene. The combined organic layers are washed with 5% NaOH (50:50 H20/ethanol), H20, dried over MGSO4 and concentrated under reduced pressure to yield 0.15-0.19 mole of >90% pure product.
  • Using the aforedescribed general procedures, the following compounds were prepared.
    Figure imgb0008
    Figure imgb0009
    Figure imgb0010
    Figure imgb0011
    Figure imgb0012
    Figure imgb0013
    Figure imgb0014
    Figure imgb0015
  • The compounds of this invention have been found to exhibit considerable biological activity. They are especially potent pesticides when used to control or combat important agricultural pests. These compounds can be used in various ways to achieve biological action. 'They can be applied per se, as solids or in vaporized form, but are preferably applied as the toxic components in pesticidal compositions of the compound and a carrier. The compositions can be applied as dusts, as liquid sprays, or as gas-propelled sprays and can contain, in addition to a carrier, additives such as emulsifying agents, wetting agents, binding agents, gases compressed to the liquid state, odorants and stabilizers. A wide variety of liquid and solid carriers can be used in the pesticidal compositions. Examples of liquid carriers include water, organic solvents such as alcohols, ketones, amides, and esters, mineral oils such as kerosene, light oils, and medium oils, and vegetable oils such as cottonseed oil. Examples of solid carriers include talc, bentonite, diatomaceous earth, pyrophyllite, fullers earth, gypsum, flours derived from cottonseeds and nut shells, and various natural and synthetic clays having a pH not exceeding about 9.5.
  • The amount of the compounds of this invention utilized in pesticidal compositions will vary rather widely. It depends to some extent upon the type of composition in which the material is being used, the nature of the condition to be controlled, and the method of application (e.i., spraying, dusting, etc.). In the ultimate pesticidal composition, as applied in the field, pesticide concentrations as low as 0.0001 weight percent of the total composition can be used. In general, compositions, as applied, containing 0.05 weight percent pesticide in either liquid or solid carrier, give excellent results. In some cases, however, stronger dosages up to 10 weight percent may be required.
  • In practice, pesticidal compositions are usually prepared in the form of concentrates, which are diluted in the field to the concentration desired for application. For example, the concentrate can be a wettable powder containing large amounts of the compound of this invention, a carrier (e.g., attapulgite or other clay), and wetting and dispersing agents. Such powders can be diluted prior to application, by dispersing it in water to obtain a sprayable suspension containing the concentration of pesticide desired for application. Other concentrates can be solutions that can be later diluted, e.g., with kerosene. Thus, it is within the contemplation of this invention to provide pesticidal compositions containing up to 80%, by weight of the composition, of a pesticidal compound of this invention. Accordingly, depending upon whether it is ready for application or it is in concentrated form, the contemplated pesticidal compositions contain between 0.0001 percent and about 80 percent, by weight of the compositions, of a pesticidal compound of this invention and a carrier, liquid or solid, as defined hereinbefore.
    • INSECTICIDE TEST METHODS Bait Test [Housefly (Adult)] Method of Treatment
  • One milliliter of an aqueous solution or suspension of the candidate compound is pipetted into a 9 cm. petri dish containing filter paper and 0.1 gm. granular sugar. Ten adults are admitted and the dish is closed.
    • Method of Recording Results
  • Mortality is recorded after 24-75 hours. Compounds which produce 90% mortality are reevaluated at lower concentrations in secondary tests. Mode of action may be by stomach poison, contact or vapor.
    • Stomach Poison - Foliar Dip Test Primary Screen
  • Southern Armyworm (Larva) Mexican Bean Beetle (Larva)
    • Method of Treatment
  • Lima bean leaves of a uniform size are momentarily dipped in a 500 ppm. water-acetone of the test material. Treated leaves are placed on moistened filter paper in 9 cm. petri dishes and allowed to air dry, and then are infested. The dishes are then closed.
    • Method of Recording Results
  • Mortality is recorded 72 hours after infestation. Compounds active at 500 ppm. are retested at 100 and 10 ppm.
  • All test results are recorded as percent mortality. In the tabulation of data, the insect species are abbreviated as follows: Housefly (HF), Mexican Bean Beetle (MB), and Southern Armyworm (SA).
  • Examples 1 to 8 were subjected to the aforedescribed insecticide tests. Test concentrations and results are set forth in the Table.
    Figure imgb0016

Claims (8)

1. A compound having the formula:
Figure imgb0017
wherein R is halogen, C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C1-C6 alkylthio, C1-C6 haloalkyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, difluoromethylthio, C1-C6 alkylamino, cyano, nitro, C1-C6 carboalkoxy, C1-C6 alkylsulphonyl, C1-C6 alkoxy Cl-C6 alkyl, C2-C6 haloalkenyl, or C1-C6 acyl; n is 0-5, R1 and R2 are hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkylcycloalkyl (C3-C6), or C2-C6 alkenyl.
2. A compound of Claim 1 having the formula:
Figure imgb0018
3. A compound of Claim 1 having the formula:
Figure imgb0019
4. A compound of Claim 1 having the formula:
Figure imgb0020
5. A compound of Claim 1 having the formula:
Figure imgb0021
6. A compound of Claim 1 having the formula:
Figure imgb0022
7. An insecticidal composition comprising a carrier and an insecticidal amount of a compound according to any one of claims 1 to 6.
8. The method of combatting insects that comprises contacting them with an insecticidal amount of a compound according to any one of claims 1 to 6.
EP81301623A 1980-04-28 1981-04-14 Amidoximether insecticides Withdrawn EP0039168A1 (en)

Applications Claiming Priority (2)

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US06/144,758 US4268525A (en) 1980-04-28 1980-04-28 Amidoximether insecticides
US144758 1993-10-29

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995024383A1 (en) * 1994-03-10 1995-09-14 Bayer Aktiengesellschaft Oxime derivatives and their use as pesticides
EP1125931A1 (en) * 2000-02-17 2001-08-22 Hunan Research Institute of Chemical Industry Biocidal alkyl-substituted-(hetero)aryl-ketoxime-O-ethers and the production method thereof

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU568028B2 (en) * 1984-07-31 1987-12-10 Commonwealth Scientific And Industrial Research Organisation Oxime insecticides
IL75858A (en) * 1984-07-31 1989-02-28 Commw Scient Ind Res Org Substituted benzyl ethers of oximes,their production and their use as arthropodicides
JP2696342B2 (en) * 1988-06-27 1998-01-14 日本曹達株式会社 Amidine derivative, method for producing the same, acaricide and agricultural / horticultural fungicide
EP0881207A4 (en) * 1996-07-30 1999-11-24 Nippon Soda Co 2,3-dihalogeno-6-trifluoromethylbenzene derivatives and processes for the preparation thereof
US20050215433A1 (en) * 2004-03-26 2005-09-29 Benitez Francisco M Aromatic fluid as agricultural solvent
US8110608B2 (en) 2008-06-05 2012-02-07 Ecolab Usa Inc. Solid form sodium lauryl sulfate (SLS) pesticide composition
US8968757B2 (en) 2010-10-12 2015-03-03 Ecolab Usa Inc. Highly wettable, water dispersible, granules including two pesticides

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4079149A (en) * 1977-06-30 1978-03-14 Shell Oil Company Benzyl oxime ethers
EP0024888A2 (en) * 1979-08-24 1981-03-11 Rhone-Poulenc Inc. Ketoximinoether insecticides

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3394181A (en) * 1964-06-29 1968-07-23 Sterling Drug Inc Phenoxy-lower-alkyl-amidoximes and phenylamino-lower-alkyl-amidoximes
US4152454A (en) * 1976-12-22 1979-05-01 Fmc Corporation Insecticidal compositions comprising N'-aryl-N-methylformamidines and 3-phenoxybenzyl carboxylates
US4183957A (en) * 1978-09-25 1980-01-15 The Dow Chemical Company N'-(substituted phenyl)-N-(2-(halophenoxy)ethyl)alkylanimidamides

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4079149A (en) * 1977-06-30 1978-03-14 Shell Oil Company Benzyl oxime ethers
EP0024888A2 (en) * 1979-08-24 1981-03-11 Rhone-Poulenc Inc. Ketoximinoether insecticides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS Vol. 78, No. 7, 19 February 1973 Columbus, Ohio, USA E. ZIEGLER et al. "Reaction of Amideoxime Ethers with Malonic Acids in Acetic Anhydride" page 486, column 1, Abstract No. 43406q & Zeitschrift fur Naturforschung B Vol. 27, No 10, 1972, pages 1169 to 1171 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995024383A1 (en) * 1994-03-10 1995-09-14 Bayer Aktiengesellschaft Oxime derivatives and their use as pesticides
US6177463B1 (en) 1994-03-10 2001-01-23 Bayer Aktiengesellschaft Oxime derivatives and their use as pesticides
EP1125931A1 (en) * 2000-02-17 2001-08-22 Hunan Research Institute of Chemical Industry Biocidal alkyl-substituted-(hetero)aryl-ketoxime-O-ethers and the production method thereof

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JPS56167660A (en) 1981-12-23
US4268525A (en) 1981-05-19

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