WO2000017154A1 - Composes de tris-oxime pesticides - Google Patents

Composes de tris-oxime pesticides Download PDF

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Publication number
WO2000017154A1
WO2000017154A1 PCT/EP1999/006953 EP9906953W WO0017154A1 WO 2000017154 A1 WO2000017154 A1 WO 2000017154A1 EP 9906953 W EP9906953 W EP 9906953W WO 0017154 A1 WO0017154 A1 WO 0017154A1
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WO
WIPO (PCT)
Prior art keywords
plants
formula
compounds
compound
active ingredient
Prior art date
Application number
PCT/EP1999/006953
Other languages
English (en)
Inventor
Hugo Ziegler
Stephan Trah
Original Assignee
Bayer Aktiengesellschaft
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 Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU61930/99A priority Critical patent/AU6193099A/en
Priority to JP2000574064A priority patent/JP2002526469A/ja
Priority to EP99948797A priority patent/EP1115698A1/fr
Publication of WO2000017154A1 publication Critical patent/WO2000017154A1/fr

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Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
    • C07C251/60—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/61—Carboxylic acid nitriles containing cyano groups and nitrogen atoms being part of imino groups bound to the same carbon skeleton

Definitions

  • the invention relates to novel pesticidally, in particular fungicidally, active tris-oxime compounds of formula I
  • R 2 is hydrogen, methyl or ethyl
  • R 3 is hydrogen, halogen, cyano, d-C 4 alkyl, C C 4 alkoxy, C 2 -C 4 alkenyl, C 2 -C alkynyl or halomethyl; n is 1 or 2.
  • the formula I embraces all stereoisomeric forms and mixtures thereof, such as racemic and diasteromeric mixtures, for example E/Z mixtures.
  • the compounds according to the invention exhibit improved biological properties which render them very suitable for practical use in agriculture and horticulture by having an extraordinarily good fungicidal activity, especially in cereals.
  • the invention furthermore relates to the preparation of these compounds, to agrochemical compositions which comprise, as active ingredients, at least one of these compounds, and to the use of the active ingredients or of the compositions for protecting plants against attack by harmful microorganisms, in particular fungi.
  • C C alkyl on its own or as structural element of other groups such as alkoxy, is methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl or tert-butyl.
  • Alkenyl is straight-chain or branched, for example vinyl, allyl, methallyl, 1-methyivinyl or but-
  • Alkynyl is straight-chain or branched, for example ethynyl, propargyl, but-1 -yn-1 -yl, but-1 -yn-
  • Halogen or halo is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine.
  • Halomethyl may contain identical or different halogen atoms; examples are fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, difluorochloromethyl, dichlorofluoromethyl; trifluoromethyl being preferred.
  • R 2 is methyl
  • R 3 is fluoro, chloro or bromo, CrC 4 alkyl, C ⁇ -C 4 alkoxy, ethynyl or trifluoromethyl.
  • U is a leaving group, for example chlorine, bromine, iodine, mesyloxy or tosyloxy
  • the compounds of formula I can be used in the agricultural sector and related fields preventively and/or curatively as active ingredients in the control of plant diseases.
  • the compounds of formula I according to the invention are distinguished by having good activity even at low rates of concentration, by being well tolerated by plants and by being environmentally friendly. They possess very advantageous, especially systemic, properties and can be used for the protection of a large number of cultivated plants. With the compounds of formula I it is possible to inhibit or destroy the pests that occur on plants or on parts of plants (the fruit, blossom, leaves, stems, tubers or roots) of various crops of useful plants, while parts of plants that grow later are also protected against phytopathogenic microorganisms, in particular fungi.
  • the compounds I can also be used as dressings in the treatment of seed (fruit, tubers, grains) and plant cuttings to provide protection against fungus infections as well as against phytopathogenic fungi that occur in the soil
  • the compounds I are effective, for example, against phytopathogenic fungi belonging to the following classes Fungi imperfecti (e.g. Botrytis, Py ⁇ cularia, Helminthospo ⁇ um, Fusa ⁇ um, Septo ⁇ a, Cercospora und Altema ⁇ a); Basidiomycetes (e.g Rhizoctonia, Hemileia, Pucc- inia), Ascomycetes (e g Ventu ⁇ a and Erysiphe, Podosphaera, Monilinia, Uncinula) and Oomycetes (e g Phytophthora, Pythium, Plasmopara).
  • Fungi imperfecti e.g. Botrytis, Py ⁇ cularia, Helminthospo ⁇ um, Fusa ⁇ um, Septo ⁇ a, Cercospora und Altema ⁇ a
  • Basidiomycetes e.g Rhizoctonia, Hemileia, Pucc- inia
  • Ascomycetes e
  • target crops for plant protection use include, for example, the following species of plants: cereals (wheat, barley, rye, oats, rice, maize, sorghum and related crops); beet (sugar beet and fodder beet), pomes, stone fruit and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries), leguminous plants (beans, lentils, peas, soybeans), oil plants (rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans, groundnuts), cucumber plants (marrows, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); citrus fruit (oranges, lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); lauraceae (avocados, cinnamon, camphor), and plants such as tobacco, nuts, coffee
  • the compounds I are usually used in the form of compositions and can be applied to the area or plant to be treated simultaneously or in succession with further active ingredients
  • further active ingredients may be, for example, fertilisers, micronut ⁇ ent donors or other preparations that influence plant growth It is also possible to use selective herbicides, and insecticides, fungicides, bacte ⁇ cides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or other application-promoting adjuvants customarily employed in formulation technology
  • Suitable carriers and adjuvants may be solid or liquid and are the substances usefully employed in formulation technology, for example natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilisers.
  • a preferred method of applying a compound of formula I, or an agrochemical composition comprising at least one of those compounds, is application to the foliage of the plants (foliar application).
  • the frequency and the rate of application depend upon the risk of infestation by the pathogen in question.
  • the compounds of formula I can also penetrate the plants through the roots via the soil (systemic action) if the locus of the plants is impregnated with a liquid formulation or if the active ingredients are incorporated into the soil in solid form, e.g. in granular form (soil application). In the case of paddy rice crops, such granules may be applied in metered amounts to the flooded rice field.
  • the compounds of formula I may, however, for seed treatment, also be applied to the seed grains (coating), either by impregnating the seeds or tubers with a liquid formulation of the active ingredient or by coating them with a solid formulation.
  • the compounds of formula I are used in unmodified form or, preferably, together with the adjuvants conventionally employed in formulation technology.
  • they are advantageously formulated in known manner e.g. into emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts or granules, for example by encapsulation in e.g. polymer substances.
  • the methods of application such as spraying, atomising, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.
  • Advantageous rates of application are generally from 1 g to 2 kg of active ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kg a.i./ha, especially from 20 g to 600 g a.i./ha.
  • rates of from 10 mg to 1 g of active ingredient per kg of seed are advantageously used.
  • compositions, preparations or mixtures comprising the compound (active ingredient) of formula I and, where appropriate, a solid or liquid adjuvant are prepared in known manner, e.g. by homogeneously mixing and/or grinding the active ingredient with extenders, such as solvents, solid carriers and, where appropriate, surface-active compounds (surfactants).
  • extenders such as solvents, solid carriers and, where appropriate, surface-active compounds (surfactants).
  • the agrochemical compositions normally comprise 0.1 to 99 % by weight, especially 0.1 to 95 % by weight, compound of formula I, 99.9 to 1 % by weight, especially 99.8 to 5 % by weight, of a solid or liquid adjuvant, and 0 to 25 % by weight, especially 0.1 to 25 % by weight, of a surfactant.
  • the compounds of formula I can be mixed with other fungicides, producing in some cases unexpected synergistic effects.
  • Especially preferred mixing partners are azoles such as azaconazole, bitertanol, propiconazole, difenoconazole, diniconazole, cyproconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, tebuconazole, tetraconazole, fenbuconazole, metconazole, myclobutanil, perfurazoate, penconazole, bromuconazole, pyrifenox, prochloraz, triadimefon, triadimenol, triflumizole or triticonazole; pyrimidinyl carbinoles such as ancymidol, fenarimol or nuarimol; 2-amino- pyrimidine such as bupirimate, dimethirimol or ethiri
  • Example B-1 Action against Puccinia qraminis on wheat a) Residual-protective action
  • wheat plants are sprayed to drip point with an aqueous spray mixture (0.02 % active ingredient), prepared from a wettable powder formulation of the active ingredient, and infected 24 hours later with a uredospore suspension of the fungus. After an incubation period of 48 hours (conditions: 95-100 % relative humidity at 20°), the plants are placed in a greenhouse at 22°. Fungus infestation is evaluated 12 days after infection. In this test compounds 1 , 3, 5, 7, 8 and 10 of Table 1 showed an efficacy of 80% or more.
  • wheat plants are watered with an aqueous spray mixture (0.006 % active ingredient, based on the volume of the soil), prepared from a wettable powder formulation of the active ingredient. Care is taken that the spray mixture does not come into contact with parts of the plants that are above the soil.
  • the plants are infected 48 hours later with a uredospore suspension of the fungus. After an incubation period of 48 hours (conditions 95-100 % relative humidity at 20°), the plants are placed in a greenhouse at 22°. Fungus infestation is evaluated 12 days after infection.
  • Example B-2 Action against Phvtophthora infestans on tomatoes a) Residual-protective action
  • aqueous spray mixture (0.02 % active ingredient), prepared from a wettable powder formulation of the active ingredient, and infected 24 hours later with a sporangia suspension of the fungus. Fungus infestation is evaluated 5 days after infection, a relative humidity of 90 to 100 % and a temperature of 20° having been maintained during that period. b) Systemic action
  • tomato plants are watered with an aqueous spray mixture (0.006 % active ingredient, based on the volume of the soil) prepared from a wettable powder formulation of the active ingredient. Care is taken that the spray mixture does not come into contact with parts of the plants that are above the soil. After 48 hours, the plants are infected with a sporangia suspension of the fungus. Fungus infestation is evaluated 5 days after infection, a relative humidity of 90 to 100 % and a temperature of 20° having been maintained during that period.
  • aqueous spray mixture 0.006 % active ingredient, based on the volume of the soil
  • Care is taken that the spray mixture does not come into contact with parts of the plants that are above the soil.
  • the plants are infected with a sporangia suspension of the fungus. Fungus infestation is evaluated 5 days after infection, a relative humidity of 90 to 100 % and a temperature of 20° having been maintained during that period.
  • Example B-3 Action against Plasmopara viticola on vines
  • Vine seedlings at the 4- to 5-leaf stage are sprayed to drip point with an aqueous spray mixture (0.02 % active ingredient), prepared from a wettable powder formulation of the active ingredient, and infected 24 hours later with a sporangia suspension of the fungus.
  • an aqueous spray mixture (0.02 % active ingredient), prepared from a wettable powder formulation of the active ingredient, and infected 24 hours later with a sporangia suspension of the fungus.
  • Fungus infestation is evaluated 6 days after infection, a relative humidity of 95 to100 % and a temperature of 20° having been maintained during that period.
  • Example B-4 Residual-protective action against Venturia inaequalis on apples Apple cuttings with 10-20 cm long fresh shoots are sprayed to drip point with an aqueous spray mixture (0.02 % active ingredient), prepared from a wettable powder formulation of the active ingredient, and infected 24 hours later with a conidia suspension of the fungus. The plants are incubated for 5 days at 90-100 % relative humidity and placed in a greenhouse for a further 10 days at 20-24°. Fungus infestation is evaluated 12 days after infection.
  • Example B-5 Action against Erysiphe graminis on barley a) Residual-protective action
  • Barley plants about 8 cm in height are watered with an aqueous spray mixture (0.002 % active ingredient, based on the volume of the soil) prepared from a wettable powder formulation of the active ingredient. Care is taken that the spray mixture does not come into contact with parts of the plants that are above the soil. The plants are dusted 48 hours later with conidia of the fungus. The infected plants are placed in a greenhouse at 22°. Fungus infestation is evaluated 12 days after infection.

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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

La présente invention concerne de nouveaux composés de tris-oxime pesticides de formule (I) dans laquelle R2 représente hydrogène, méthyle ou éthyle; R3 représente hydrogène, halogène, cyano, C1-C4alkyle, C1-C4alcoxy, C2-C4alkynyle ou halométhyle; et n est égal à 1 ou 2. Ces nouveaux composés, qui présentent des propriétés phytoprotectrices, peuvent servir à protéger les plantes contre les infestations par des micro-organismes phytopathogènes.
PCT/EP1999/006953 1998-09-22 1999-09-20 Composes de tris-oxime pesticides WO2000017154A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU61930/99A AU6193099A (en) 1998-09-22 1999-09-20 Pesticidal tris-oxime compounds
JP2000574064A JP2002526469A (ja) 1998-09-22 1999-09-20 有害生物防除性トリス−オキシム化合物
EP99948797A EP1115698A1 (fr) 1998-09-22 1999-09-20 Composes de tris-oxime pesticides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9820582.6 1998-09-22
GBGB9820582.6A GB9820582D0 (en) 1998-09-22 1998-09-22 Organic compounds

Publications (1)

Publication Number Publication Date
WO2000017154A1 true WO2000017154A1 (fr) 2000-03-30

Family

ID=10839236

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/006953 WO2000017154A1 (fr) 1998-09-22 1999-09-20 Composes de tris-oxime pesticides

Country Status (5)

Country Link
EP (1) EP1115698A1 (fr)
JP (1) JP2002526469A (fr)
AU (1) AU6193099A (fr)
GB (1) GB9820582D0 (fr)
WO (1) WO2000017154A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995018789A1 (fr) * 1994-01-05 1995-07-13 Ciba-Geigy Ag Pesticides
WO1997020809A1 (fr) * 1995-12-07 1997-06-12 Novartis Ag Pesticides

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995018789A1 (fr) * 1994-01-05 1995-07-13 Ciba-Geigy Ag Pesticides
WO1997020809A1 (fr) * 1995-12-07 1997-06-12 Novartis Ag Pesticides

Also Published As

Publication number Publication date
GB9820582D0 (en) 1998-11-11
EP1115698A1 (fr) 2001-07-18
JP2002526469A (ja) 2002-08-20
AU6193099A (en) 2000-04-10

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