WO1992004318A1 - Carbonates d'oxime utilises comme fongicides - Google Patents

Carbonates d'oxime utilises comme fongicides Download PDF

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Publication number
WO1992004318A1
WO1992004318A1 PCT/US1991/005588 US9105588W WO9204318A1 WO 1992004318 A1 WO1992004318 A1 WO 1992004318A1 US 9105588 W US9105588 W US 9105588W WO 9204318 A1 WO9204318 A1 WO 9204318A1
Authority
WO
WIPO (PCT)
Prior art keywords
dimethylamino
methyl
compounds
naphthylmethyl
naphthyl
Prior art date
Application number
PCT/US1991/005588
Other languages
English (en)
Inventor
John Benjamin Adams, Jr.
Original Assignee
E.I. Du Pont De Nemours And Company
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 E.I. Du Pont De Nemours And Company filed Critical E.I. Du Pont De Nemours And Company
Publication of WO1992004318A1 publication Critical patent/WO1992004318A1/fr

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Classifications

    • 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
    • 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
    • A01N47/06—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 containing —O—CO—O— groups; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/60—Thiocarboxylic acids having sulfur atoms of thiocarboxyl groups further doubly-bound to oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

Definitions

  • Hubele CH 66-16,259 claims compounds of Formula ii as
  • EP 0010588 U.S. equivalents 4,449,999, 4,394,152, 4,451,279 and 4,382,893 discloses the use of compounds of Formula vi as herbicide safeners.
  • R is H, Cl, F or C 1 -C 3 alkyl.
  • This invention pertains to compounds of the Formula (I) including all geometric and stereoisomers, agricultural compositions containing them and their use as fungicides
  • Y is Cl or SO 2 R 4 ; wherein the aromatic rings of R 1 are optionally substituted with methyl, methoxy, nitro or 1-2 halogen;
  • R 2 and R 3 are independently H or C 1 -C 4 alkyl; or R 2 and R 3 can be taken together along with the nitrogen atom to which they are attached to form a pyrrolidino, piperidino or morpholino group, said pyrrolidino, piperidino or
  • morpholino group being optionally substituted with 1-2 methyl
  • Q 1 is C 1 -C 4 normal alkyl; and Q 2 is C 1 -C 3 normal alkyl optionally substituted with 1-2 methyl, or a direct bond.
  • R 4 is methyl, phenyl or benzyl.
  • R 1 is naphthylmethyl or naphthyl(2-ethyl).
  • R 2 and R 3 are both methyl or R 2 and R 3 are taken together along with the nitrogen atom to which they are attached to form a piperidino group.
  • Method A the carboxamide II reacts with the chloroformate llI in an inert solvent in the presence of an acid scavenger (base).
  • suitable solvents include polar aprotic solvents such as acetonitrile and ethyl acetate; ethers such as tetrahydrofuran (THF), dimethoxyethane and diethyl ether; ketones such as acetone and
  • N,N-diethylanilin d N,N-dimethylaniline The reaction temperature can range from about -20 to +50°C, and the reaction time from about 5 minutes to several days depending on choice of reactants, solvent and temperature.
  • the carboxamide II can be made as described in U.S.
  • chloroformates III can be made by methods well-known in the art and exemplified in this specification. However, it is also known in the art that some chloroformates are unstable, readily generating relatively stable cations [(R 1 ) + in this case], most generally for the compounds llI wherein R 1 is a secondary or tertiary benzylic-type group, with loss of CO 2 and formation of alkyl chloride. In those cases Method B is preferred.
  • compounds of Formula (I) are O-substituted oximes and, as such, may exist in the syn or antiform, or mixtures thereof.
  • the scope of this invention includes both the syn and antiforms and mixtures thereof as they are likely to occur.
  • oxime chloroformates that can be similarly prepared include, but are not limited to:
  • Useful formulations of the compounds of Formula (I) can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly.
  • Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare.
  • High strength compositions are primarily used as intermediates for further formulation.
  • the formulations broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:
  • Emulsifiers Annual MC PubHshing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents",
  • the ingredients are blended, hammer-milled until all the solids are substantially under 50 microns, reblended, and packaged.
  • the ingredients are blended, coarsely hammer-milled and then airmilled to produce particles substantially all below 10 microns in
  • the product is reblended before packaging.
  • a slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.
  • the ingredients are blended, hammer-milled and then moistened with about 12% water.
  • the mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings).
  • the granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.
  • Example F Highly aliphatic hydrocarbon oil 70% The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspensions may be applied directly, but preferably after being extended with oils or emulsified in water.
  • Example F The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspensions may be applied directly, but preferably after being extended with oils or emulsified in water.
  • the ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles substantially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.
  • Example H The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.
  • Example H The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.
  • the ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.
  • the active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been comp'eted, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.
  • the ingredients are blended and milled to pass through a 100 mesh screen.
  • This material is then added to a fluid-bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material.
  • the fluidization and spraying are continued until granules of the desired size range are made.
  • the spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%.
  • the material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.
  • the ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening).
  • the concentrate may be formulated further if necessary.
  • Example M The ingredients are blended and ground in a hammer-mill to produce particles substantially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged.
  • Example M The ingredients are blended and ground in a hammer-mill to produce particles substantially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged.
  • the ingredients are thoroughly blended, coarsely hammer-m i lled and then air-milled to produce particles essentially all below 10 microns in size.
  • the material is reblended and then packaged.
  • the ingredients are combined and stirred together to produce a solution.
  • the product can be extended with oils, or emulsified in water.
  • the compounds of this invention are useful as plant disease control agents. They provide control of diseases caused by a broad spectrum of fungal plant pathogens in the Basidiomycete, Ascomycete and Oomycete classes. They are effective in controlling a broad spectrum of plant diseases, particularly foliar pathogens of ornamental, vegetable, field, cereal, and fruit crops. These pathogens include, Venturia inaequalis, Cercosporidium personatum, Cercospora arachidicola, Cercospora beticola, Pseudocercosporella herpotrichoides, Puccinia recpndita,
  • Puccinia gramminis Hemileia yastatrix, Puccinia striiformis, Puccinia arachidis, Pyricularia oryzae, Phytophthora infestans, Plasmopara viticola, Peronospora tabacina, Pseudoperonospora cubensis, Pythium aphanidermatum, Botrytis cinerea, Monilinia fructicola, and other species closely related to these pathogens. They also control seed pathogens. In particular the compounds of this invention are exceptional in their ability to provide control of diseases for an extended period of time after application.
  • the compounds of this invention can be mixed with fungicides, bactericides, acaricides, nematicides, insecticides or other biologically active compounds in order to achieve desired results with a minimum of expenditure of time, effort and material.
  • Suitable agents of this type are well-known to those skilled in the art. Some are listed below:
  • Rates of application for these compounds can be influenced by many factors of the environment and should be determined under actual use conditions. Foliage can normally be protected when treated at a rate of from less than 10 g/ha to 10,000 g/ha of active ingredient. Plants growing in soil treated at a concentration from 0.1 to about 20 kg/ha can be protected from disease. Seed and seedlings can normally be protected when seed is treated at a rate of from 0.1 to 10 g per kilogram of seed.
  • test compounds were dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem 014 (polyhydric alcohol esters). This suspension was sprayed to the point of run-off on peanut seedlings. The following day the seedlings were inoculated with a spore suspension of Cercosporidium personatum (the causal agent of peanut late leafspot) and incubated in a saturated atmosphere at 22°C for 24 hrs., a high humidity atmosphere at 22 to 30°C for 5 days, and then moved to a growth chamber at 29°C for 6 days, after which disease ratings were made.
  • a spore suspension of Cercosporidium personatum the causal agent of peanut late leafspot

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

Abstract

On décrit des carbonates d'oxime sélectionnés de la formule (I) et leurs compositions stéréoisomères et géométriques agricoles contenant de tels composés ainsi que leur utilisation en tant que fongicides. Dans la formule (I), Y représente Cl ou SO2R4; R1 représente (a),(b), (c), ou (d), et les anneaux aromatiques représentés par R1 sont éventuellement substitués; R2 et R3 représentent indépendamment H ou C¿1?-C4 alkyle; ou R?2 et R3¿ peuvent être pris ensemble avec l'atome d'azote auquel ils sont liés pour former éventuellement un anneau hétérocyclique substitué; R4 représente phényle, naphthyle; cycloalkyle; ou C¿1?-C12 alkyle éventuellement substitué avec C1-C2 alcoxy, C5-C6 cycloalkyle, phényle ou naphthyle; Q?1¿ représente alkylène, Q2 représente alkylène ou une liaison directe.
PCT/US1991/005588 1990-08-29 1991-08-14 Carbonates d'oxime utilises comme fongicides WO1992004318A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US57307390A 1990-08-29 1990-08-29
US573,073 1990-08-29

Publications (1)

Publication Number Publication Date
WO1992004318A1 true WO1992004318A1 (fr) 1992-03-19

Family

ID=24290530

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1991/005588 WO1992004318A1 (fr) 1990-08-29 1991-08-14 Carbonates d'oxime utilises comme fongicides

Country Status (4)

Country Link
CN (1) CN1059712A (fr)
AU (1) AU8499491A (fr)
IL (1) IL99324A0 (fr)
WO (1) WO1992004318A1 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2119700A1 (de) * 1970-04-23 1971-12-23 E.I. Du Pont De Nemours And Co., Wilmington, Del. (V.St.A.) Acetamid-S-oxid-Verbindungen und ihre Herstellung und Anwendung

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2119700A1 (de) * 1970-04-23 1971-12-23 E.I. Du Pont De Nemours And Co., Wilmington, Del. (V.St.A.) Acetamid-S-oxid-Verbindungen und ihre Herstellung und Anwendung

Also Published As

Publication number Publication date
IL99324A0 (en) 1992-07-15
CN1059712A (zh) 1992-03-25
AU8499491A (en) 1992-03-30

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