WO1998041094A1 - Fungicide mixture - Google Patents

Fungicide mixture Download PDF

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Publication number
WO1998041094A1
WO1998041094A1 PCT/EP1998/001034 EP9801034W WO9841094A1 WO 1998041094 A1 WO1998041094 A1 WO 1998041094A1 EP 9801034 W EP9801034 W EP 9801034W WO 9841094 A1 WO9841094 A1 WO 9841094A1
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WIPO (PCT)
Prior art keywords
co2ch3
compound
phenyl
noch
compounds
Prior art date
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PCT/EP1998/001034
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German (de)
French (fr)
Inventor
Oliver Wagner
Herbert Bayer
Ulf Misslitz
Ulrich Schirmer
Eberhard Ammermann
Gisela Lorenz
Siegfried Strathmann
Original Assignee
Basf Aktiengesellschaft
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Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to AU67240/98A priority Critical patent/AU6724098A/en
Publication of WO1998041094A1 publication Critical patent/WO1998041094A1/en

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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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues 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
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products

Definitions

  • the present invention relates to a fungicidal mixture which
  • R is a C-organic residue which is directly or via a
  • n 0, 1, 2 or 3, where the radicals X can be different if n is greater than 1;
  • X is cyano, nitro, halogen, C ⁇ -C -alkyl, C 4 haloalkyl, C ⁇ -C 4 -alkoxy, C 4 haloalkoxy, C ⁇ -C4-alkylthio;
  • n> 1 a C 3 -C 5 alkylene, C 3 -C 5 alkenylene, oxy-C 2 -C 4 alkylene, oxy bonded to two adjacent C atoms of the phenyl ring -C ⁇ -C 3 -alkyl- noxy-, oxy-C -C 4 -alkenylene, oxy-C 2 -C 4 -alkenyleneoxy or butadienediyl group, these chains in turn can carry one to three of the following radicals: halogen, C ⁇ -C 4 alkyl, C 1 -C 4 haloalkyl, C ⁇ -C 4 -alkoxy, C 4 -haloalkoxy or C ⁇ -C 4 alkylthio,
  • Y C- or -N-;
  • Q cyclopentenyl, cyclohexenyl, phenyl, pyrrolyl, thienyl, furyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, triazolyl, pyridinyl, 2-pyridonyl, pyrimidinyl and triazinyl;
  • the invention also relates to processes for the preparation Derar ⁇ term mixtures, and using the mixtures, for combating harmful fungi in the field of crop and Materialschut ⁇ zes.
  • the herbicidal active ingredient II (trade name: Dicamba) is from the literature (cf. for example "The Pesticide Manual", British Crop Protection Council, 10th edition 1994; US-A 3,013,054), for example for combating broad-leaved plants in cereals (as Herbicide) as well as an auxin-like growth regulator.
  • Active ingredient III (proposed trade name: diflufenzopyr) is also known from the literature (cf. AGROW No. 261, Aug. 2, 1996) as a herbicide with an auxin transport-inhibiting action.
  • the active ingredients IA and IB are, for example, in the following
  • the present invention was based on the object of mixtures which are suitable when using smaller amounts of the compounds IA and IB to develop an improved action against the harmful fungi (synergistic action).
  • Aryloxy optionally subst. Hetaryloxy, optionally subst. Aryl oxymethylene, if necessary subst. Hetaryloxymethylene, optionally subst. Aryl - ethenylene, optionally subst.
  • R ⁇ , R ß R ⁇ , R ⁇ and R ⁇ in general and in particular those in the have the meanings described below: EP-A 370 629, EP-A 414 153, EP-A 426 460, EP-A 460 575, EP-A 463 488, EP-A 472 300, EP-A 498 188, EP A 498 396, EP-A 515 901, EP-A 585 751, EP-A 619 301, EP-A 658 547, WO-A 90 / 07,493,
  • radicals "optionally substituted aryloxy, optionally substituted hetaryloxy" generally and in particular correspond to the meanings described in the following documents: EP-A 178 826, EP-A 242 070, EP-A 242 081, EP- A 253 213, EP-A 254 426, EP-A 256 667, EP-A 260 794, EP-A 280 185, EP-A 307 103, EP-A 341 845, EP-A 382 375, EP-A 393 861, EP-A 398 692, EP-A 405 782, EP-A 430 471, EP-A 468 684, EP-A 468 695, EP-A 477 631, EP-A 483 985, EP-A 498 188, EP-A 513 580, EP-A 515 901, EP-A 623 604, EP-A 634 405, EP-A 647 631, EP-A 658 547, EP-A 667 343, EP-A 669
  • radicals "optionally substituted aryloxymethylene, optionally substituted hetaryloxymethylene” generally and in particular correspond to those described in the following documents Meanings: EP-A 178 826, EP-A 226 917, EP-A 253 213, EP-A 254 426, EP-A 278 595, EP-A 280 185, EP-A 299 694,
  • radicals "optionally substituted arylethenylene, optionally substituted hetarylethenylene” generally and in particular correspond to the meanings described in the following documents: EP-A 178 826, EP-A 203 606, EP-A 253 213, EP- A 254 426, EP-A 280 185, EP-A 378 755, EP-A 398 692, EP-A 402 246,
  • EP-A 474 042 EP-A 475 158, EP-A 477 631, EP-A 487 409, EP-A 498 188, EP-A 498 396, EP-A 513 580, EP-A 515 901, EP- A 528 245, EP-A 544 587, EP-A 658 547, EP-A 669 315, EP-A 691 332, WO-A 93 / 15,046, WO-A 94 / 11,334, WO-A 95 / 01,973, WO -A 96 / 17,851, WO-A 96 / 22,983, WO-A 96 / 31,463, WO-A 96 / 35,669, WO-A 96 / 35,690, and FR-A 2 670 781.
  • EP-A 398 692 EP-A 463 488, EP-A 477 631, EP-A 515 901, EP-A 579 124, EP-A 585 751, EP-A 617 014, EP-A 621 277 , EP-A 622 355, EP-A 623 604, EP-A 627 411, EP-A 628 540, EP-A 647 631, EP-A 656 351, EP-A 667 343, EP-A 669 315, EP -A 669 319, EP-A 673 923, EP-A 691 332,
  • R ' represents -N (OCH 3 ) C0 2 CH 3 , -N (CH 3 ) -C0 2 CH 3 or -N (CH 2 CH 3 ) -C0 2 CH 3 , correspond in general and in particular to the compounds described in the following documents: EP-A 498 396, EP-A 619
  • n has the value 0, R "for optionally subst.
  • active ingredients IA or IB and II When preparing the mixtures, preference is given to using the pure active ingredients IA or IB and II, to which, as required, further active ingredients can be added to combat pests (e.g. insects, arachnids or nematodes) or harmful fungi or else herbicidal or growth-regulating active ingredients or fertilizers.
  • pests e.g. insects, arachnids or nematodes
  • harmful fungi e.g. insects, arachnids or nematodes
  • herbicidal or growth-regulating active ingredients or fertilizers e.g. insects, arachnids or nematodes
  • mixtures of the compounds IA or IB and II or the simultaneous joint or separate use of the compounds IA and II or IB and II are distinguished by an excellent action against a broad spectrum, in particular of phytopathogenic fungi. They are partly systemically effective (i.e. when used for crop protection, they can be absorbed by the treated plant without loss of activity and possibly transported in the plant) and can therefore also be used as leaf and soil fungicides.
  • Botrytis cinerea (gray mold) on strawberries, vegetables, ornamental plants and vines
  • Erysiphe graminis (powdery mildew) on cereals, Fusarium and Verticillium species on various plants, Helmin thosporium species on cereals, Mycosptiaerella species on bananas,
  • the mixtures according to the invention are also suitable for combating harmful fungi such as Paecilomyces variotii in the protection of materials (e.g. wood, paper, dispersions for addressing, fibers or fabrics) and in the protection of stored goods.
  • harmful fungi such as Paecilomyces variotii in the protection of materials (e.g. wood, paper, dispersions for addressing, fibers or fabrics) and in the protection of stored goods.
  • the compounds IA or IB and II and / or III can be applied simultaneously, that is together or separately or in succession, the sequence in the case of separate application generally not having any effect on the success of the control measures.
  • the compounds IA and II or IB and II are usually in a weight ratio of 10: 1 to 0.1: 1, preferably 5: 1 to 0.2: 1, in particular 2: 1 to 0.5: 1 (IA: II or IB: II) applied.
  • the compounds IA or IB and III are usually in a weight ratio of 25: 1 to 0.25: 1, preferably
  • the compounds IA or IB and II and III are usually in a weight ratio of 10: 1: 0.4 to 0.1: 1: 0.4, preferably 5: 1: 0.4 to 0.2: 1: 0 , 4, in particular 2: 1: 0.4 to 0.5: 1: 0.4 (IA: II: III or IB: II: III), applied.
  • the application rates of the mixtures according to the invention are from 2 to 0.1 kg / ha, preferably from 1.25 to 0.2 kg / ha, in particular from 0.75 to 0.3, depending on the type of effect desired kg / ha.
  • the application rates for the compounds IA and IB are 1 to 0.01 kg / ha, preferably 0.5 to 0.02 kg / ha, in particular 0.25 to 0.03 kg / ha.
  • the application rates for the compounds II are generally from 0.5 to 0.001 kg / ha, preferably 0.25 to 0.005 kg / ha, in particular 0.1 to 0.01 kg / ha.
  • the application rates for the compound III are in general from 0.001 to 0.3 kg / ha, preferably 0.005 to 0.2 kg / ha, into ⁇ particular 0.01 to 0.1 kg / ha.
  • the mixing ratios with respect to the compounds II and III are generally 4: 1, preferably 3: 1, in particular 2.5: 1 (II: III).
  • application rates of mixture of 0.1 to 100 g / 100 kg of seed, preferably 0.5 to 50 g / 100 kg of seed, in particular 1 to 10 g / 100 kg of seed, are generally used.
  • the application rates of the mixtures according to the invention are from 0.01 to 20 g / m 3 , preferably 0.05 to 10 g / m 3 , in particular 0.1 to 5, depending on the type of effect desired g / m 3 .
  • the compounds IA or IB and II and / or III or the mixtures of the compounds IA or IB and II and / or III are applied jointly or separately by spraying or dusting the seeds, the Plants or the soil before or after sowing the plants or before or after the plants germinate.
  • the fungicidal synergistic mixtures according to the invention or the compounds IA or IB and II and / or III can be used, for example, in the form of directly sprayable solutions, powders and suspensions or in the form of high-strength aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, pastes , Dusts, scattering agents or granules are prepared and applied by spraying, atomizing, dusting, scattering or pouring.
  • the form of application depends on the intended use; in any case, it should ensure as fine and uniform a distribution of the mixture according to the invention as possible.
  • the formulations are prepared in a manner known per se, for example by adding solvents and / or carriers.
  • Inert additives such as emulsifiers or dispersants are usually added to the formulations.
  • the surface-active substances are the alkali, alkaline earth and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acid, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa- , Hepta- and octadecanols or fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, poly
  • Powders, materials for broadcasting and dusts can be prepared by mixing or jointly grinding the compounds IA or IB and II and / or III or the mixtures of the compounds IA or IB and II and / or III with a solid carrier.
  • Granules e.g. coating, impregnation or homogeneous granules
  • a solid carrier e.g., a wax, a wax, or a wax.
  • Mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics serve as fillers or solid carriers, for example. and fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • the formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of one of the compounds IA or IB or II or III or the mixture of the compounds IA or IB and II and / or III.
  • the active ingredients are in a purity of 90% to
  • the compounds IA, IB, II and III or their mixtures or the corresponding formulations are used by adding the harmful fungi, their habitat or those prior to fungal attack protective materials, plants, seeds, soils, areas or spaces with a fungicidally effective amount of the mixture or of the compounds IA or IB and II and / or III treated separately.
  • the treatment can be carried out before or after the 5 infection by the harmful fungi.
  • the active compounds were prepared separately or together as a 10% emulsion in a mixture of 67% by weight cyclohexanone and 23% by weight 5 emulsifier and diluted with water in accordance with the desired concentration.
  • W (1 - ⁇ ) -100 / ß 5 ⁇ corresponds to the fungal attack of the treated plants in% and ß corresponds to the fungal attack of the untreated (control) plants in%
  • the infection of the treated plants corresponds to that of the untreated control plants; at an efficiency of 100, the treated plants showed no infection.

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  • 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)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention relates to a fungicide mixture with synergistic effect, containing a) a fungicide active compound of formula IA or IB wherein - - - represents a single or double bond and the index and substituents have the following meanings: R' -C[CO2CH3] =CHOCH3, -C[CO2CH3] =NOCH3, -C[CONHCH3] =NOCH3, -C[CO2CH3] =CHCH3, -C[CO2CH3] =CHCH2CH3, -C[COCH3] =NOCH3, -C[COCH2CH3] =NOCH3, -N(OCH3) -CO2CH3, -N(CH3) -CO2CH3, -N(CH2CH3) -CO2CH3; R'' a C-organic radical which is bonded directly or via an oxy-, mercapto-, amino- or alkylamino group; together with a group X and the ring Q or T to which they are bonded, an optionally substituted bicyclic, partially or completely unsaturated system; Rx -OC[CO¿2?CH3] =CHOCH3, -OC[CO2CH3] =CHCH3, -OC[CO2CH3] =CHCH2CH3, -SC[CO2CH3] =CHOCH3, -SC[CO2CH3] =CHCH3, -SC[CO2CH3] =CHCH2CH3, -N(CH3)C[CO2CH3] =CHOCH3, -N(CH3)C[CO2CH3] =NOCH3, -CH2C[CO2CH3] =CHOCH3, -CH2C[CO2CH3] =NOCH3, -CH2C[CONHCH3] =NOCH3; R?y¿ oxygen, sulfur, =CH- or =N-; n 0, 1, 2 or 3; X cyano, nitro, halogen, alkyl, halogenalkyl, alkoxy, halogenalkoxy, alkylthio; if n⊃1, an optionally substituted alkylene, alkenylene, oxyalkylene, oxyalkylenoxy, oxyalkenylene, oxyalkenylenoxy or butadiendiyl group bonded to two adjoining C-atoms of the phenyl ring; Y C- or -N-; Q cyclopentenyl, cyclohexenyl, phenyl, pyrrolyl, thienyl, furyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, triazolyl, pyridinyl, 2-pyridonyl, pyrimidinyl and triazinyl; T phenyl, oxazolyl, thiazolyl, thiadiazolyl, oxadiazolyl, pyridinyl, pyrimidinyl and triazinyl, and b) the herbicide active agent II and/or b2) the herbicide active agent III. The invention also relates to methods for producing mixtures of that type and the use of such mixtures for combatting harmful fungi in the area of plant and material protection.

Description

Fungizide MischungFungicidal mixture
Beschreibungdescription
Die vorliegende Erfindung betrifft eine fungizide Mischung, welcheThe present invention relates to a fungicidal mixture which
a) eine fungizid wirksame Verbindung der Formel IA bzw. IBa) a fungicidally active compound of the formula IA or IB
Figure imgf000003_0001
in denen Z- ^ für eine Einfach- oder Doppelbindung steht und der Index und die Substituenten die folgende Bedeutung haben:
Figure imgf000003_0001
in which Z - ^ stands for a single or double bond and the index and the substituents have the following meaning:
R' -C[C02CH3]=CHOCH3, -C [C02CH3] =NOCH3 , -C [CONHCH3] =NOCH3 , -C [C02CH3] =CHCH3 , -C [C02CH3] =CHCH2CH3 , -C [COCH3] =NOCH3 , -C [COCH2CH3] =NOCH3, -N(OCH3) -C02CH3 , -N(CH3) -C02CH3, -N(CH2CH3) -C02CH3 ;R '-C [C0 2 CH 3] = CHOCH 3, -C [C0 2 CH 3] = NOCH 3, -C [CONHCH 3] = NOCH 3, -C [C0 2 CH 3] = CHCH 3, -C [C0 2 CH 3 ] = CHCH 2 CH 3 , -C [COCH 3 ] = NOCH 3 , -C [COCH 2 CH 3 ] = NOCH 3 , -N (OCH 3 ) -C0 2 CH 3 , -N (CH 3 ) -C0 2 CH 3 , -N (CH 2 CH 3 ) -C0 2 CH 3 ;
R" ein C-organischer Rest, welcher direkt oder über eineR "is a C-organic residue which is directly or via a
Oxy-, Mercapto-, Amino-, oder Alkylaminogruppe gebunden ist;Oxy, mercapto, amino, or alkylamino group;
zusammen mit einer Gruppe X und dem Ring Q bzw. T, an den sie gebunden sind, ein ggf. subst. bicyclisches, partiell oder vollständig ungesättigtes System, welches neben Kohlenstoffringgliedern Heteroatome aus der Gruppe Sauerstoff, Schwefel und Stickstoff enthalten kann;together with a group X and the ring Q or T to which they are attached, a subst. bicyclic, partially or completely unsaturated system which, in addition to carbon ring members, can contain heteroatoms from the group consisting of oxygen, sulfur and nitrogen;
RX -OC[C02CH3]=CHOCH3, -OC [C02CH3] =CHCH3,R X -OC [CO 2 CH 3 ] = CHOCH 3 , -OC [CO 2 CH 3 ] = CHCH 3 ,
-OC [C02CH3] =CHCH2CH3, -SC [C02CH3] =CHOCH3 , -SC [C02CH3] =CHCH3, -SC [C02CH3] =CHCH2CH3, -N(CH3)C[C02CH3]=CHOCH3, -N(CH3)C [C02CH3] =NOCH3 , -CH2C [CO2CH3] =CHOCH3 , -CH2C [C02CH3] =N0CH3 , -CH2C [CO HCH3] =NOCH3 ;-OC [C0 2 CH 3 ] = CHCH 2 CH 3 , -SC [C0 2 CH 3 ] = CHOCH 3 , -SC [C0 2 CH 3 ] = CHCH 3 , -SC [C0 2 CH 3 ] = CHCH 2 CH 3, -N (CH 3) C [C0 2 CH 3] = CHOCH 3, -N (CH 3) C [C0 2 CH 3] = NOCH 3, -CH 2 C [CO 2 CH 3] = CHOCH 3, -CH 2 C [CO 2 CH 3 ] = NOCH 3 , -CH 2 C [CO HCH 3 ] = NOCH 3 ;
RV Sauerstoff, Schwefel, =CH- oder =N- ;RV oxygen, sulfur, = CH- or = N-;
n 0, 1, 2 oder 3, wobei die Reste X verschieden sein kön- nen, wenn n größer als 1 ist; X Cyano, Nitro, Halogen, Cι-C -Alkyl, Cι-C4-Halogenalkyl, Cι-C4-Alkoxy, Cι-C4-Halogenalkoxy, Cι-C4-Alkylthio;n is 0, 1, 2 or 3, where the radicals X can be different if n is greater than 1; X is cyano, nitro, halogen, Cι-C -alkyl, C 4 haloalkyl, Cι-C 4 -alkoxy, C 4 haloalkoxy, Cι-C4-alkylthio;
für den Fall, daß n > 1 ist, eine an zwei benachbarte C-Atome des Phenylrings gebundene C3-C5-Alkylen-, C3-C5-Alkenylen-, Oxy-C2-C4-alkylen-, Oxy-Cι-C3-alkyle- noxy-, Oxy-C -C4-alkenylen-, Oxy-C2-C4-alkenylenoxy- oder Butadiendiylgruppe, wobei diese Ketten ihrerseits ein bis drei der folgenden Reste tragen können: Halogen, Cι-C4-Alkyl, C1-C4-Halogenalkyl, Cι-C4-Alkoxy, Cι-C4-Halogenalkoxy oder Cι-C4-Alkylthio,in the event that n> 1, a C 3 -C 5 alkylene, C 3 -C 5 alkenylene, oxy-C 2 -C 4 alkylene, oxy bonded to two adjacent C atoms of the phenyl ring -Cι-C 3 -alkyl- noxy-, oxy-C -C 4 -alkenylene, oxy-C 2 -C 4 -alkenyleneoxy or butadienediyl group, these chains in turn can carry one to three of the following radicals: halogen, Cι -C 4 alkyl, C 1 -C 4 haloalkyl, Cι-C 4 -alkoxy, C 4 -haloalkoxy or Cι-C 4 alkylthio,
Y =C- oder -N-;Y = C- or -N-;
Q Cyclopentenyl, Cyclohexenyl, Phenyl, Pyrrolyl, Thienyl, Furyl, Pyrazolyl, Imidazolyl, Oxazolyl, Isoxazolyl, Thiazolyl, Thiadiazolyl, Triazolyl, Pyridinyl, 2-Pyrido- nyl, Pyrimidinyl und Triazinyl;Q cyclopentenyl, cyclohexenyl, phenyl, pyrrolyl, thienyl, furyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, triazolyl, pyridinyl, 2-pyridonyl, pyrimidinyl and triazinyl;
Phenyl, Oxazolyl, Thiazolyl, Thiadiazolyl, Oxadiazolyl, Pyridinyl, Pyrimidinyl und Triazinyl,Phenyl, oxazolyl, thiazolyl, thiadiazolyl, oxadiazolyl, pyridinyl, pyrimidinyl and triazinyl,
sowiesuch as
bl) den herbiziden Wirkstoff IIbl) the herbicidal active ingredient II
Figure imgf000004_0001
Figure imgf000004_0001
und/oderand or
b2) den herbiziden Wirkstoff IIIb2) the herbicidal active ingredient III
Figure imgf000004_0002
in einer synergistisch wirksamen Menge enthalten.
Figure imgf000004_0002
contained in a synergistically effective amount.
Außerdem betrifft die Erfindung Verfahren zu Herstellung derar¬ tiger Mischungen sowie zur Verwendung der Mischungen zur Bekämp- fung von Schadpilzen im Bereich des Pflanzen- und Materialschut¬ zes . Der herbizide Wirkstoff II (Handelsname: Dicamba) ist aus der Literatur (vgl. z.B. "The Pesticide Manual", British Crop Pro- tection Council, 10 Aufl. 1994; US-A 3,013,054) beispielsweise zur Bekämpfung von breitblättrigen Pflanzen in Getreide (als Herbizid) sowie als Auxin-ähnlicher Wachstumsregulator bekannt.The invention also relates to processes for the preparation Derar ¬ term mixtures, and using the mixtures, for combating harmful fungi in the field of crop and Materialschut ¬ zes. The herbicidal active ingredient II (trade name: Dicamba) is from the literature (cf. for example "The Pesticide Manual", British Crop Protection Council, 10th edition 1994; US-A 3,013,054), for example for combating broad-leaved plants in cereals (as Herbicide) as well as an auxin-like growth regulator.
Der Wirkstoff III (vorgeschlagener Handelsname: Diflufenzopyr) ist ebenfalls aus der Literatur (vgl. AGROW No. 261, 02. Aug. 1996) als Herbizid mit Auxin-transport-hemmender Wirkung be- kannt.Active ingredient III (proposed trade name: diflufenzopyr) is also known from the literature (cf. AGROW No. 261, Aug. 2, 1996) as a herbicide with an auxin transport-inhibiting action.
Die Wirkstoffe IA und IB sind beispielsweise in den folgendenThe active ingredients IA and IB are, for example, in the following
Schriften beschrieben: EP-A 178 826, EP-A 203 606, EP-A 203 608, EP-A 206 523, EP-A 212 859 EP-A 226 917, EP-A 229 974, EP-A 242 070 EP-A 242 081 EP-A 243 012 EP-A 243 014, EP-A 251 082 EP-A 253 213 EP-A 254 426 EP-A 256 667, EP-A 260 794 EP-A 260 832 EP-A 267 734 EP-A 273 572, EP-A 274 825 EP-A 278 595 EP-A 280 185 EP-A 291 196, EP-A 299 694 EP-A 307 101 EP-A 307 103 EP-A 310 954, EP-A 312 221 EP-A 312 243 EP-A 329 011 EP-A 331 966, EP-A 335 519 EP-A 336 211 EP-A 337 211 EP-A 341 845, EP-A 350 691 EP-A 354 571 EP-A 363 818 EP-A 370 629, EP-A 373 775 EP-A 374 811 EP-A 378 308 EP-A 378 755, EP-A 379 098 EP-A 382 375 EP-A 383 117 EP-A 384 211, EP-A 385 224 EP-A 385 357 EP-A 386 561 EP-A 386 681, EP-A 389 901 EP-A 391 451 EP-A 393 428 EP-A 393 861, EP-A 398 692 EP-A 400 417 EP-A 402 246 EP-A 405 782, EP-A 407 873 EP-A 409 369 EP-A 414 153 EP-A 416 746, EP-A 420 091 EP-A 422 597 EP-A 426 460 EP-A 429 968, EP-A 430 471 EP-A 433 233 EP-A 433 899 EP-A 439 785, EP-A 459 285 EP-A 460 575 EP-A 463 488 EP-A 463 513, EP-A 464 381 EP-A 468 684 EP-A 468 695 EP-A 468 775, EP-A 471 261 EP-A 472 224 EP-A 472 300 EP-A 474 042, EP-A 475 158 EP-A 477 631 EP-A 480 795 EP-A 483 851, EP-A 483 985 EP-A 487 409 EP-A 493 711 EP-A 498 188, EP-A 498 396 EP-A 499 823 EP-A 503 436 EP-A 508 901, EP-A 509 857 EP-A 513 580 EP-A 515 901 EP-A 517 301, EP-A 528 245 EP-A 532 022 EP-A 532 126 EP-A 532 127, EP-A 535 980 EP-A 538 097 EP-A 544 587 EP-A 546 387, EP-A 548 650 EP-A 564 928 EP-A 566 455 EP-A 567 828, EP-A 571 326 EP-A 579 071 EP-A 579 124 EP-A 579 908, EP-A 581 095 EP-A 582 902 EP-A 582 925 EP-A 583 806, EP-A 584 625 EP-A 585 751 EP-A 590 610 EP-A 596 254, EP-A 611 760 EP-A 617 014 EP-A 619 301 EP-A 621 277, EP-A 622 355 EP-A 623 604 EP-A 627 411 EP-A 628 540, EP-A 634 405 EP-A 647 631 EP-A 656 351 EP-A 658 547, EP-A 667 343 EP-A 669 315 EP-A 669 319 EP-A 672 347, EP-A 673 923, EP-A 684 225, EP-A 684 226, EP-A 691 332, EP-A 704 430, EP-A 711 759, EP-A 718 292, EP-A 731 095, EP-A 738 708, EP-A 738 716, WO-A 90/07,493, WO-A 92/13,830, WO-A 92/18,487, WO-A 92/18,494, WO-A 92/21,653, WO-A 93/07,116, WO-A 93/08,180, WO-A 93/08,183, WO-A 93/15,046 WO-A 93/16 986, WO-A 94/00,436, WO-A 94/05,626, WO-A 94/08,948 WO-A 94/08 968, WO-A 94/10,159, WO-A 94/11,334, WO-A 94/14,322 WO-A 94/14 761, WO-A 94/17,060, WO-A 94/19,331, WO-A 94/22,812 WO-A 94/23 576, WO-A 94/26,705, WO-A 95/01,973, WO-A 95/05,367 WO-A 95/05 368, WO-A 95/06,033, WO-A 95/06,039, WO-A 95/14,015 WO-A 95/14 674, WO-A 95/18,789, WO-A 95/21,153, WO-A 95/21,154 WO-A 95/24 396, WO-A 95/25,095, WO-A 95/29,896, WO-A 95/30,639 WO-A 95/32 182, WO-A 96/01,256, WO-A 96/01,258, WO-A 96/11,183 WO-A 96/14 305, WO-A 96/16,029, WO-A 96/16,030, WO-A 96/16,044 WO-A 96/16 047, WO-A 96/16,933, WO-A 96/16,943, WO-A 96/17,851 WO-A 96/22 983, WO-A 96/29,301, WO-A 96/29,305, WO-A 96/31,463 WO-A 96/31 484, WO-A 96/32,399, WO-A 96/33,164, WO-A 96/35,690 WO-A 96/35 669, WO-A 96/37,480, WO-A 96/37,477, WO-A 97/00,862 WO-A 97/01 545, WO-A 97/01,544, WO-A 97/01,530, JP-A 02/121,970, JP-A 04/182,461, JP-A 05/201,946, JP-A 05/201,980, JP-A 05/255,012, JP-A 05/294,948, JP-A 06/025,133, JP-A 06/025,142, JP-A 06/056,756, JP-A 06/087,842, JP-A 06/184,127, JP-A 06/271,525, JP-A 07/025,840, JP-A 07/145,137, JP-A 07/224,041, JP-A 07/278,090, JP-A 07/330,735, JP-A 08/012,648, JP-A 08/027,133, JP-A 08/127,563, JP-A 08/188,565, FR-A 2 670 781, GB-A 2 210 041, GB-A 2 218 702, GB-A 2 238 308, GB-A 249 092, GB-A 2 253 624, GB-A 2 255 092, GB-A 2 276 380, GB-A 276 381, DE-A 39 05 911 und DE-A 43 14 272, DE An . Nr. 19 528 651, DE Anm. Nr. 19 534 492, DE Anm. Nr. 19 540 361, DE Anm. Nr. 19 541 382, DE Anm. Nr. 19 545 094 und DE Anm. Nr. 19 618 852Writings described: EP-A 178 826, EP-A 203 606, EP-A 203 608, EP-A 206 523, EP-A 212 859 EP-A 226 917, EP-A 229 974, EP-A 242 070 EP -A 242 081 EP-A 243 012 EP-A 243 014, EP-A 251 082 EP-A 253 213 EP-A 254 426 EP-A 256 667, EP-A 260 794 EP-A 260 832 EP-A 267 734 EP-A 273 572, EP-A 274 825 EP-A 278 595 EP-A 280 185 EP-A 291 196, EP-A 299 694 EP-A 307 101 EP-A 307 103 EP-A 310 954, EP -A 312 221 EP-A 312 243 EP-A 329 011 EP-A 331 966, EP-A 335 519 EP-A 336 211 EP-A 337 211 EP-A 341 845, EP-A 350 691 EP-A 354 571 EP-A 363 818 EP-A 370 629, EP-A 373 775 EP-A 374 811 EP-A 378 308 EP-A 378 755, EP-A 379 098 EP-A 382 375 EP-A 383 117 EP- A 384 211, EP-A 385 224 EP-A 385 357 EP-A 386 561 EP-A 386 681, EP-A 389 901 EP-A 391 451 EP-A 393 428 EP-A 393 861, EP-A 398 692 EP-A 400 417 EP-A 402 246 EP-A 405 782, EP-A 407 873 EP-A 409 369 EP-A 414 153 EP-A 416 746, EP-A 420 091 EP-A 422 597 EP- A 426 460 EP-A 429 968, EP-A 430 471 EP-A 433 233 EP-A 433 899 EP-A 439 785, EP-A 459 285 EP-A 460 575 EP-A 4 63 488 EP-A 463 513, EP-A 464 381 EP-A 468 684 EP-A 468 695 EP-A 468 775, EP-A 471 261 EP-A 472 224 EP-A 472 300 EP-A 474 042, EP-A 475 158 EP-A 477 631 EP-A 480 795 EP-A 483 851, EP-A 483 985 EP-A 487 409 EP-A 493 711 EP-A 498 188, EP-A 498 396 EP-A 499 823 EP-A 503 436 EP-A 508 901, EP-A 509 857 EP-A 513 580 EP-A 515 901 EP-A 517 301, EP-A 528 245 EP-A 532 022 EP-A 532 126 EP -A 532 127, EP-A 535 980 EP-A 538 097 EP-A 544 587 EP-A 546 387, EP-A 548 650 EP-A 564 928 EP-A 566 455 EP-A 567 828, EP-A 571 326 EP-A 579 071 EP-A 579 124 EP-A 579 908, EP-A 581 095 EP-A 582 902 EP-A 582 925 EP-A 583 806, EP-A 584 625 EP-A 585 751 EP -A 590 610 EP-A 596 254, EP-A 611 760 EP-A 617 014 EP-A 619 301 EP-A 621 277, EP-A 622 355 EP-A 623 604 EP-A 627 411 EP-A 628 540, EP-A 634 405 EP-A 647 631 EP-A 656 351 EP-A 658 547, EP-A 667 343 EP-A 669 315 EP-A 669 319 EP-A 672 347, EP-A 673 923, EP-A 684 225, EP-A 684 226, EP-A 691 332, EP-A 704 430, EP-A 711 759, EP-A 718 292, EP-A 731 095, EP- A 738 708, EP-A 738 716, WO-A 90 / 07,493, WO-A 92 / 13,830, WO-A 92 / 18,487, WO-A 92 / 18,494, WO-A 92 / 21,653, WO-A 93 / 07,116, WO-A 93 / 08,180, WO-A 93 / 08,183, WO-A 93 / 15,046 WO-A 93/16 986, WO-A 94 / 00,436, WO-A 94 / 05,626, WO-A 94 / 08,948 WO-A 94/08 968, WO-A 94 / 10.159, WO-A 94 / 11.334, WO-A 94 / 14.322 WO-A 94/14 761, WO-A 94 / 17.060, WO-A 94 / 19.331, WO-A 94 / 22,812 WO-A 94/23 576, WO-A 94 / 26.705, WO-A 95 / 01.973, WO-A 95 / 05.367 WO-A 95/05 368, WO-A 95 / 06.033, WO -A 95 / 06.039, WO-A 95 / 14.015 WO-A 95/14 674, WO-A 95 / 18.789, WO-A 95 / 21.153, WO-A 95 / 21.154 WO-A 95/24 396, WO- A 95 / 25,095, WO-A 95 / 29,896, WO-A 95 / 30,639 WO-A 95/32 182, WO-A 96 / 01,256, WO-A 96 / 01,258, WO-A 96 / 11,183 WO-A 96 / 14 305, WO-A 96 / 16,029, WO-A 96 / 16,030, WO-A 96 / 16,044 WO-A 96/16 047, WO-A 96 / 16,933, WO-A 96 / 16,943, WO-A 96 / 17,851 WO-A 96/22 983, WO-A 96 / 29,301, WO-A 96 / 29,305, WO-A 96 / 31,463 WO-A 96/31 484, WO-A 96 / 32,399, WO-A 96 / 33,164, WO-A 96 / 35,690 WO-A 96/35 669, WO-A 96 / 37,480, WO-A 96 / 37,477, WO-A 97 / 00,862 WO-A 97/01 545 , WO-A 97 / 01,544, WO-A 97 / 01,530, JP-A 02 / 121,970, JP-A 04 / 182,461, JP-A 05 / 201,946, JP-A 05 / 201,980, JP-A 05 / 255,012, JP-A 05 / 294,948, JP-A 06 / 025,133, JP-A 06 / 025,142, JP-A 06 / 056,756, JP-A 06 / 087,842, JP-A 06 / 184,127, JP-A 06 / 271,525, JP -A 07 / 025,840, JP-A 07 / 145,137, JP-A 07 / 224,041, JP-A 07 / 278,090, JP-A 07 / 330,735, JP-A 08 / 012,648, JP-A 08 / 027,133, JP- A 08 / 127,563, JP-A 08 / 188,565, FR-A 2 670 781, GB-A 2 210 041, GB-A 2 218 702, GB-A 2 238 308, GB-A 249 092, GB-A 2 253 624, GB-A 2 255 092, GB-A 2 276 380, GB-A 276 381, DE-A 39 05 911 and DE-A 43 14 272, DE An. No. 19 528 651, DE Note No. 19 534 492, DE Note No. 19 540 361, DE Note No. 19 541 382, DE Note No. 19 545 094 and DE Note No. 19 618 852
Der vorliegenden Erfindung lagen Mischungen als Aufgabe zugrunde, die geeignet sind bei Einsatz geringerer Mengen an den- Verbindungen IA und IB eine verbesserte Wirkung gegen die Schad- pilze zu entfalten (synergistische Wirkung) .The present invention was based on the object of mixtures which are suitable when using smaller amounts of the compounds IA and IB to develop an improved action against the harmful fungi (synergistic action).
Demgemäß wurden die eingangs definierten Mischungen gefunden. Außerdem wurden Verfahren zu Herstellung dieser Mischungen sowie die Verwendung der Mischungen zur Bekämpfung von Schadpilzen im Bereich des Pflanzen- und Materialschutzes gefunden.We have found that this object is achieved by the mixtures defined at the outset. In addition, processes for the preparation of these mixtures and the use of the mixtures for controlling harmful fungi in the field of plant and material protection were found.
Für die erfindungsgemäßen Mischungen eignen sich grundsätzlich alle in den eingangs angeführten Schriften angeführten Verbindungen des Typs IA bzw. IB, deren gemeinsames Merkmal darin besteht, daß sie die mitochondrialen Atmungskette der Schadpilze auf der Stufe des b/ci-Komplexes hemmen.For the mixtures according to the invention, all compounds of type IA or IB listed in the documents mentioned at the outset, and their common feature, are suitable in principle consists in that they inhibit the mitochondrial respiratory chain of the harmful fungi at the level of the b / ci complex.
Von besonderer Bedeutung sind dabei Verbindungen IA und IB, in denen R" für eine der folgenden Gruppen steht:Of particular importance are compounds IA and IB in which R "represents one of the following groups:
ggf. subst. Aryloxy, ggf. subst. Hetaryloxy, ggf. subst. Aryl- oxymethylen, ggf. subst. Hetaryloxymethylen, ggf. subst. Aryl - ethenylen, ggf. subst. Hetarylethenylen, oder eine Gruppe RαRßC=NOCH2- oder RvON=CRδCRε=NOCH2 wobei die Reste Rα, Rß Rγ, Rδ und Rε im allgemeinen und im besonderen die in den folgenden Schriften beschriebenen Bedeutungen haben: EP-A 370 629, EP-A 414 153, EP-A 426 460, EP-A 460 575, EP-A 463 488, EP-A 472 300, EP-A 498 188, EP-A 498 396, EP-A 515 901, EP-A 585 751, EP-A 619 301, EP-A 658 547, WO-A 90/07,493,if necessary subst. Aryloxy, optionally subst. Hetaryloxy, optionally subst. Aryl oxymethylene, if necessary subst. Hetaryloxymethylene, optionally subst. Aryl - ethenylene, optionally subst. Hetarylethenylene, or a group R α R ß C = NOCH 2 - or R v ON = CR δ CR ε = NOCH 2 where the radicals R α , R ß R γ , R δ and R ε in general and in particular those in the have the meanings described below: EP-A 370 629, EP-A 414 153, EP-A 426 460, EP-A 460 575, EP-A 463 488, EP-A 472 300, EP-A 498 188, EP A 498 396, EP-A 515 901, EP-A 585 751, EP-A 619 301, EP-A 658 547, WO-A 90 / 07,493,
WO-A 92/13,830, WO-A 92/18,487, WO-A 92/18,494, WO-A 93/15,046, WO-A 93/16,986, WO-A 94/08,948, WO-A 94/08,968, WO-A 94/14,322, WO-A 94/14,761, WO-A 95/01,973, WO-A 95/18,789, WO-A 95/21,153, WO-A 95/21,154, WO-A 96/11,183, WO-A 96/14,305, WO-A 96/16,030, WO-A 96/16,044, WO-A 96/16,943, WO-A 96/17,851, WO-A 96/22,983, WO-A 96/31,463, WO-A 96/35,669 WO-A 97/01,544, WO-A 97/01,545, WO-A 97/01,530, JP-A 05/201,946, JP-A 05/255,012, JP-A 05/294,948, JP-A 06/025,133, JP-A 06/025,142, GB-A 2 276 380, DE Anm. Nr. 19 528 651, DE Anm. Nr. 19 534 492, DE Anm. Nr. 19 540 361, DE Anm. Nr. 19 541 382, 19 545 094 und DE Anm. Nr. 19 618 852.WO-A 92 / 13,830, WO-A 92 / 18,487, WO-A 92 / 18,494, WO-A 93 / 15,046, WO-A 93 / 16,986, WO-A 94 / 08,948, WO-A 94 / 08,968, WO -A 94 / 14.322, WO-A 94 / 14.761, WO-A 95 / 01.973, WO-A 95 / 18.789, WO-A 95 / 21.153, WO-A 95 / 21.154, WO-A 96 / 11.183, WO- A 96 / 14,305, WO-A 96 / 16,030, WO-A 96 / 16,044, WO-A 96 / 16,943, WO-A 96 / 17,851, WO-A 96 / 22,983, WO-A 96 / 31,463, WO-A 96 / 35,669 WO-A 97 / 01,544, WO-A 97 / 01,545, WO-A 97 / 01,530, JP-A 05 / 201,946, JP-A 05 / 255,012, JP-A 05 / 294,948, JP-A 06 / 025.133, JP-A 06 / 025.142, GB-A 2 276 380, DE No. 19 528 651, DE No. 19 534 492, DE No. 19 540 361, DE No. 19 541 382, 19 545 094 and DE Note No. 19 618 852.
Besonders bevorzugte Reste "ggf. subst. Aryloxy, ggf. subst. Hetaryloxy" entsprechen im allgemeinen und im besonderen den in den folgenden Schriften beschriebenen Bedeutungen: EP-A 178 826, EP-A 242 070, EP-A 242 081, EP-A 253 213, EP-A 254 426, EP-A 256 667, EP-A 260 794, EP-A 280 185, EP-A 307 103, EP-A 341 845, EP-A 382 375, EP-A 393 861, EP-A 398 692, EP-A 405 782, EP-A 430 471, EP-A 468 684, EP-A 468 695, EP-A 477 631, EP-A 483 985, EP-A 498 188, EP-A 513 580, EP-A 515 901, EP-A 623 604, EP-A 634 405, EP-A 647 631, EP-A 658 547, EP-A 667 343, EP-A 669 315, EP-A 731 095, WO-A 93/15,046, WO-A 94/10,159, WO-A 94/17,060, WO-A 95/01,973, WO-A 95/05,367, WO-A 95/05,368, WO-A 95/06,039, WO-A 95/14,674, WO-A 95/24,396, WO-A 95/32,182, WO-A 96/17,851, WO-A 96/22,983, WO-A 96/29,301, WO-A 96/29,305, WO-A 96/31,463, WO-A 96/35,669, WO-A 96/35,690, GB-A 2 253 624, JP-A 04/182,461, JP-A 06/184,127 und JP-A 07/330,735.Particularly preferred radicals "optionally substituted aryloxy, optionally substituted hetaryloxy" generally and in particular correspond to the meanings described in the following documents: EP-A 178 826, EP-A 242 070, EP-A 242 081, EP- A 253 213, EP-A 254 426, EP-A 256 667, EP-A 260 794, EP-A 280 185, EP-A 307 103, EP-A 341 845, EP-A 382 375, EP-A 393 861, EP-A 398 692, EP-A 405 782, EP-A 430 471, EP-A 468 684, EP-A 468 695, EP-A 477 631, EP-A 483 985, EP-A 498 188, EP-A 513 580, EP-A 515 901, EP-A 623 604, EP-A 634 405, EP-A 647 631, EP-A 658 547, EP-A 667 343, EP-A 669 315, EP- A 731 095, WO-A 93 / 15.046, WO-A 94 / 10.159, WO-A 94 / 17.060, WO-A 95 / 01.973, WO-A 95 / 05.367, WO-A 95 / 05.368, WO-A 95 / 06,039, WO-A 95 / 14,674, WO-A 95 / 24,396, WO-A 95 / 32,182, WO-A 96 / 17,851, WO-A 96 / 22,983, WO-A 96 / 29,301, WO-A 96 / 29,305, WO-A 96 / 31,463, WO-A 96 / 35,669, WO-A 96 / 35,690, GB-A 2 253 624, JP-A 04 / 182.461, JP-A 06 / 184.127 and JP-A 07 / 330.735 .
besonders bevorzugte Reste "ggf. subst. Aryloxymethylen, ggf. subst. Hetaryloxymethylen" entsprechen im allgemeinen und im besonderen den in den folgenden Schriften beschriebenen Bedeutungen: EP-A 178 826, EP-A 226 917, EP-A 253 213, EP-A 254 426, EP-A 278 595, EP-A 280 185, EP-A 299 694,Particularly preferred radicals "optionally substituted aryloxymethylene, optionally substituted hetaryloxymethylene" generally and in particular correspond to those described in the following documents Meanings: EP-A 178 826, EP-A 226 917, EP-A 253 213, EP-A 254 426, EP-A 278 595, EP-A 280 185, EP-A 299 694,
EP-A 335 519, EP-A 350 691, EP-A 363 81t EP-A 373 775, EP-A 378 308, EP-A 385 224, EP-A 386 561, EP-A 398 692, EP-A 400 417, EP-A 407 873, EP-A 472 224, EP-A 477 631, EP-A 498 188, EP-A 498 396, EP-A 513 580, EP-A 515 901, EP-A 579 124, EP-A 628 540, EP-A 658 547, EP-A 669 315,EP-A 335 519, EP-A 350 691, EP-A 363 81t EP-A 373 775, EP-A 378 308, EP-A 385 224, EP-A 386 561, EP-A 398 692, EP-A 400 417, EP-A 407 873, EP-A 472 224, EP-A 477 631, EP-A 498 188, EP-A 498 396, EP-A 513 580, EP-A 515 901, EP-A 579 124 , EP-A 628 540, EP-A 658 547, EP-A 669 315,
EP-A 672 347, EP-A 673 923, EP-A 738 716, WO-A 93/08,180, WO-A 93/15,046, WO-A 94/00,436, WO-A 94/19,331, WO-A 95/01,973, WO-A 95/14,015, WO-A 95/25,095, WO-A 95/29,896, WO-A 95/32,182, WO-A 96/01,256, WO-A 96/01,258, WO-A 96/16,029, WO-A 96/16,047, WO-A 96/17,851, WO-A 96/22,983, WO-A 96/31,463, WO-A 96/31,484, WO-A 96/35,669, WO-A 96/35,690, WO-A 96/37,477, WO-A 96/37,480, JP-A 04/182,461 und GB-A 2 276 381.EP-A 672 347, EP-A 673 923, EP-A 738 716, WO-A 93 / 08,180, WO-A 93 / 15,046, WO-A 94 / 00,436, WO-A 94 / 19,331, WO-A 95 / 01,973, WO-A 95 / 14.015, WO-A 95 / 25.095, WO-A 95 / 29.896, WO-A 95 / 32.182, WO-A 96 / 01.256, WO-A 96 / 01.258, WO-A 96 / 16,029, WO-A 96 / 16,047, WO-A 96 / 17,851, WO-A 96 / 22,983, WO-A 96 / 31,463, WO-A 96 / 31,484, WO-A 96 / 35,669, WO-A 96 / 35,690 , WO-A 96 / 37,477, WO-A 96 / 37,480, JP-A 04 / 182,461 and GB-A 2 276 381.
besonders bevorzugte Reste "ggf. subst. Arylethenylen, ggf. subst. Hetarylethenylen" entsprechen im allgemeinen und im besonderen den in den folgenden Schriften beschriebenen Bedeutungen: EP-A 178 826, EP-A 203 606, EP-A 253 213, EP-A 254 426, EP-A 280 185, EP-A 378 755, EP-A 398 692, EP-A 402 246,particularly preferred radicals "optionally substituted arylethenylene, optionally substituted hetarylethenylene" generally and in particular correspond to the meanings described in the following documents: EP-A 178 826, EP-A 203 606, EP-A 253 213, EP- A 254 426, EP-A 280 185, EP-A 378 755, EP-A 398 692, EP-A 402 246,
EP-A 474 042, EP-A 475 158, EP-A 477 631, EP-A 487 409, EP-A 498 188, EP-A 498 396, EP-A 513 580, EP-A 515 901, EP-A 528 245, EP-A 544 587, EP-A 658 547, EP-A 669 315, EP-A 691 332, WO-A 93/15,046, WO-A 94/11,334, WO-A 95/01,973, WO-A 96/17,851, WO-A 96/22,983, WO-A 96/31,463, WO-A 96/35,669, WO-A 96/35,690, und FR-A 2 670 781.EP-A 474 042, EP-A 475 158, EP-A 477 631, EP-A 487 409, EP-A 498 188, EP-A 498 396, EP-A 513 580, EP-A 515 901, EP- A 528 245, EP-A 544 587, EP-A 658 547, EP-A 669 315, EP-A 691 332, WO-A 93 / 15,046, WO-A 94 / 11,334, WO-A 95 / 01,973, WO -A 96 / 17,851, WO-A 96 / 22,983, WO-A 96 / 31,463, WO-A 96 / 35,669, WO-A 96 / 35,690, and FR-A 2 670 781.
Besonders bevorzugte Wirkstoffe der Formel IA, in denen R' für -C [C0CH3] =CHOCH3 steht, entsprechen im allgemeinen und im beson- deren den in den folgenden Schriften beschriebenen Verbindungen:Particularly preferred active compounds of the formula IA, in which R 'is —C [COCH 3 ] = CHOCH 3 , correspond in general and in particular to the compounds described in the following documents:
EP-A 178 826, EP-A 203 606 EP-A 226 917, EP-A 242 070, EP-A 242 081, EP-A 256 667 EP-A 260 794, EP-A 278 595, EP-A 299 694, EP-A 307 103 EP-A 335 519, EP-A 341 845,EP-A 178 826, EP-A 203 606 EP-A 226 917, EP-A 242 070, EP-A 242 081, EP-A 256 667 EP-A 260 794, EP-A 278 595, EP-A 299 694, EP-A 307 103 EP-A 335 519, EP-A 341 845,
EP-A 350 691 EP-A 370 629 EP-A 373 775, EP-A 378 308, EP-A 378 755 EP-A 382 375 EP-A 385 224, EP-A 386 561,EP-A 350 691 EP-A 370 629 EP-A 373 775, EP-A 378 308, EP-A 378 755 EP-A 382 375 EP-A 385 224, EP-A 386 561,
EP-A 393 861 EP-A 402 246 EP-A 405 782, EP-A 407 873,EP-A 393 861 EP-A 402 246 EP-A 405 782, EP-A 407 873,
EP-A 414 153 EP-A 426 460 EP-A 430 471, EP-A 463 488,EP-A 414 153 EP-A 426 460 EP-A 430 471, EP-A 463 488,
EP-A 468 695 EP-A 472 224 EP-A 474 042, EP-A 475 158,EP-A 468 695 EP-A 472 224 EP-A 474 042, EP-A 475 158,
EP-A 483 985 EP-A 487 409 EP-A 515 901, EP-A 528 245, EP-A 544 587 EP-A 611 760 EP-A 621 277, EP-A 622 355,EP-A 483 985 EP-A 487 409 EP-A 515 901, EP-A 528 245, EP-A 544 587 EP-A 611 760 EP-A 621 277, EP-A 622 355,
EP-A 623 604 EP-A 627 411 EP-A 634 405, EP-A 647 631,EP-A 623 604 EP-A 627 411 EP-A 634 405, EP-A 647 631,
EP-A 656 351, EP-A 667 343 EP-A 669 319, EP-A 672 347,EP-A 656 351, EP-A 667 343 EP-A 669 319, EP-A 672 347,
EP-A 673 923, EP-A 684 225 EP-A 711 759, EP-A 718 292,EP-A 673 923, EP-A 684 225 EP-A 711 759, EP-A 718 292,
EP-A 731 095, EP-A 738 716 WO-A 90/07,493, WO-A 92/18,487, WO-A 92/18,494, WO-A 93/08 180, WO-A 93/16,986, WO-A 94/00,463,EP-A 731 095, EP-A 738 716 WO-A 90 / 07,493, WO-A 92 / 18,487, WO-A 92 / 18,494, WO-A 93/08 180, WO-A 93 / 16,986, WO-A 94 / 00,463,
WO-A 94/08,948, WO-A 94/08 968, WO-A 94/10,159, WO-A 94/11,334,WO-A 94 / 08,948, WO-A 94/08 968, WO-A 94 / 10,159, WO-A 94 / 11,334,
WO-A 94/14,322, WO-A 94/14 761, WO-A 94/17,060, WO-A 94/23,576, WO-A 94/26,705, WO-A 95/05,367, WO-A 95/05,368, WO-A 95/14,674, WO-A 95/18,789, WO-A 95/21,153, WO-A 95/24,396, WO-A 95/25,095, WO-A 95/30,639, WO-A 96/11,183, WO-A 96/14,305, WO-A 96/16,047, WO-A 96/17,851, WO-A 96/22,983, WO-A 96/29,301, WO-A 96/31,463, 5 WO-A 96/31,484, WO-A 96/33,164, WO-A 96/35,690, WO-A 96/37,477, WO-A 97/00,862, WO-A 97/01,530, WO-A 97/01,545, FR-A 2 670 781, JP-A 06/025,133, JP-A 07/224,041, JP-A 08/012,648, JP-A 08/027,133, JP-A 08/127,563, GB-A 2 276 380, GB-A 2 276 381, DE-A 43 14 272, DE Anm. Nr. 19 10 528 651, DE Anm. Nr. 19 534 492, DE Anm. Nr. 19 540 361, DE Anm. Nr. 19 541 382 und DE Anm. Nr. 19 545 094.WO-A 94 / 14.322, WO-A 94/14 761, WO-A 94 / 17.060, WO-A 94 / 23.576, WO-A 94 / 26,705, WO-A 95 / 05,367, WO-A 95 / 05,368, WO-A 95 / 14,674, WO-A 95 / 18,789, WO-A 95 / 21,153, WO-A 95 / 24,396, WO -A 95 / 25,095, WO-A 95 / 30,639, WO-A 96 / 11,183, WO-A 96 / 14,305, WO-A 96 / 16,047, WO-A 96 / 17,851, WO-A 96 / 22,983, WO- A 96 / 29,301, WO-A 96 / 31,463, 5 WO-A 96 / 31,484, WO-A 96 / 33,164, WO-A 96 / 35,690, WO-A 96 / 37,477, WO-A 97 / 00,862, WO- A 97 / 01,530, WO-A 97 / 01,545, FR-A 2 670 781, JP-A 06 / 025,133, JP-A 07 / 224,041, JP-A 08 / 012,648, JP-A 08 / 027,133, JP-A 08 / 127,563, GB-A 2 276 380, GB-A 2 276 381, DE-A 43 14 272, DE note no. 19 10 528 651, DE note no. 19 534 492, DE note no. 19 540 361, DE Note No. 19 541 382 and DE Note No. 19 545 094.
besonders bevorzugte Wirkstoffe des Typs IA, in denen R' für -C [C02CH3] =NOCH3 steht, entsprechen im allgemeinen und im beson-particularly preferred active substances of type IA, in which R 'represents -C [C0 2 CH 3 ] = NOCH 3 , correspond in general and in particular
15 deren den in den folgenden Schriften beschriebenen Verbindungen: EP-A 253 213, EP-A 254 426, EP-A 299 694, EP-A 363 818, EP-A 378 308, EP-A 385 224, EP-A 386 561, EP-A 400 417, EP-A 407 873, EP-A 460 575, EP-A 463 488, EP-A 468 684, EP-A 472 300, EP-A 515 901, EP-A 611 760, EP-A 617 014,15 of the compounds described in the following documents: EP-A 253 213, EP-A 254 426, EP-A 299 694, EP-A 363 818, EP-A 378 308, EP-A 385 224, EP-A 386 561, EP-A 400 417, EP-A 407 873, EP-A 460 575, EP-A 463 488, EP-A 468 684, EP-A 472 300, EP-A 515 901, EP-A 611 760, EP-A 617 014,
20 EP-A 621 277, EP-A 622 355, EP-A 623 604, EP-A 627 411, EP-A 647 631, EP-A 656 351, EP-A 667 343, EP-A 669 319, EP-A 672 347, EP-A 673 923, EP-A 711 759, EP-A 731 095, EP-A 738 708, EP-A 738 716, WO-A 94/00,436, WO-A 94/08,948, WO-A 94/10,159, WO-A 94/11,334, WO-A 94/14,322, WO-A 94/14,761,20 EP-A 621 277, EP-A 622 355, EP-A 623 604, EP-A 627 411, EP-A 647 631, EP-A 656 351, EP-A 667 343, EP-A 669 319, EP -A 672 347, EP-A 673 923, EP-A 711 759, EP-A 731 095, EP-A 738 708, EP-A 738 716, WO-A 94 / 00,436, WO-A 94 / 08,948, WO -A 94 / 10,159, WO-A 94 / 11,334, WO-A 94 / 14,322, WO-A 94 / 14,761,
25 WO-A 95/01,973, WO-A 95/05,368, WO-A 95/06,033, WO-A 95/06,039, WO-A 95/14,015, WO-A 95/18,789, WO-A 95/21,153, WO-A 95/24,396, WO-A 95/25,095, WO-A 95/30,639, WO-A 96/11,183, WO-A 96/14,305, WO-A 96/16,047, WO-A 96/16 , 933 ,_WO-A 96/17,851, WO-A 96/22,983, WO-A 96/29,305, WO-A 96/31,463, WO-A 96/31,484, WO-A 96/33,164,25 WO-A 95 / 01,973, WO-A 95 / 05,368, WO-A 95 / 06,033, WO-A 95 / 06,039, WO-A 95 / 14,015, WO-A 95 / 18,789, WO-A 95 / 21,153, WO-A 95 / 24,396, WO-A 95 / 25,095, WO-A 95 / 30,639, WO-A 96 / 11,183, WO-A 96 / 14,305, WO-A 96 / 16,047, WO-A 96/16, 933 , _WO-A 96 / 17,851, WO-A 96 / 22,983, WO-A 96 / 29,305, WO-A 96 / 31,463, WO-A 96 / 31,484, WO-A 96 / 33,164,
30 WO-A 96/35,690, WO-A 97/00 , 862 ,_WO-A 97/01,530, WO-A 97/01,545, GB-A 2 276 380, GB-A 2 276 381, JP-A 05/201,946, JP-A 05/255,012, JP-A 05/294,948, JP-A 07/224,041, JP-A 08/012,648, JP-A 08/027,133, JP-A 08/127,563, DE Anm. Nr. 19 528 651, DE Anm. Nr. 19 534 492, DE Anm. Nr. 1930 WO-A 96 / 35,690, WO-A 97/00, 862, _WO-A 97 / 01,530, WO-A 97 / 01,545, GB-A 2 276 380, GB-A 2 276 381, JP-A 05 / 201,946, JP-A 05 / 255,012, JP-A 05 / 294,948, JP-A 07 / 224,041, JP-A 08 / 012,648, JP-A 08 / 027,133, JP-A 08 / 127,563, DE Note No. 19 528 651, DE Note No. 19 534 492, DE Note No. 19
35 540 361, DE Anm. Nr. 19 541 382 und DE Anm. Nr. 19 618 852.35 540 361, DE Note No. 19 541 382 and DE Note No. 19 618 852.
besonders bevorzugte Wirkstoffe des Typs IA, in denen R' für -C [CONHCH3] = OCH3 steht, entsprechen im allgemeinen und im besonderen den in den folgenden Schriften beschriebenenParticularly preferred active substances of type IA, in which R 'stands for -C [CONHCH 3 ] = OCH 3 , correspond in general and in particular to those described in the following documents
40 Verbindungen: EP-A 398 692, EP-A 463 488, EP-A 477 631, EP-A 515 901, EP-A 579 124, EP-A 585 751, EP-A 617 014, EP-A 621 277, EP-A 622 355, EP-A 623 604, EP-A 627 411, EP-A 628 540, EP-A 647 631, EP-A 656 351, EP-A 667 343, EP-A 669 315, EP-A 669 319, EP-A 673 923, EP-A 691 332,40 compounds: EP-A 398 692, EP-A 463 488, EP-A 477 631, EP-A 515 901, EP-A 579 124, EP-A 585 751, EP-A 617 014, EP-A 621 277 , EP-A 622 355, EP-A 623 604, EP-A 627 411, EP-A 628 540, EP-A 647 631, EP-A 656 351, EP-A 667 343, EP-A 669 315, EP -A 669 319, EP-A 673 923, EP-A 691 332,
45 EP-A 711 759, EP-A 738 716, WO-A 92/13,830, WO-A 93/08,180,45 EP-A 711 759, EP-A 738 716, WO-A 92 / 13,830, WO-A 93 / 08,180,
WO-A 94/08,948, WO-A 94/10,159, WO-A 94/11,334, WO-A 94/14,322, WO-A 94/14,761, WO-A 94/19,331, WO-A 94/22,812, WO-A 95/01,973, WO-A 95/05,368, WO-A 95/06,033, WO-A 95/14,015, WO-A 95/18,789, WO-A 95/21,154, WO-A 95/24,396, WO-A 95/30,639, WO-A 95/32,182, WO-A 96/11,183, WO-A 96/14,305, WO-A 96/16,047, WO-A 96/17,851, WO-A 96/22,983, WO-A 96/29,305, WO-A 96/31,463, WO-A 96/31,484, WO-A 96/33,164, WO-A 96/35,690, WO-A 97/00,862, WO-A 97/01,530, WO-A 97/01,545, GB-A 2 253 624, GB-A 2 276 380, GB-A 2 276 381, JP-A 04/182,461, JP-A 05/201,946, JP-A 05/255,012, JP-A 05/294,948, JP-A 06/087,842, JP-A 06/184,127, JP-A 07/025,840, JP-A 07/224,041, JP-A 08/012,648, JP-A 08/027,133, JP-A 08/127,563, DE Anm. Nr. 19 528 651,WO-A 94 / 08,948, WO-A 94 / 10,159, WO-A 94 / 11,334, WO-A 94 / 14.322, WO-A 94 / 14.761, WO-A 94 / 19.331, WO-A 94 / 22.812, WO -A 95 / 01.973, WO-A 95 / 05,368, WO-A 95 / 06,033, WO-A 95 / 14,015, WO-A 95 / 18,789, WO-A 95 / 21,154, WO-A 95 / 24,396, WO-A 95 / 30,639, WO -A 95 / 32,182, WO-A 96 / 11,183, WO-A 96 / 14,305, WO-A 96 / 16,047, WO-A 96 / 17,851, WO-A 96 / 22,983, WO-A 96 / 29,305, WO- A 96 / 31,463, WO-A 96 / 31,484, WO-A 96 / 33,164, WO-A 96 / 35,690, WO-A 97 / 00,862, WO-A 97 / 01,530, WO-A 97 / 01,545, GB-A 2 253 624, GB-A 2 276 380, GB-A 2 276 381, JP-A 04 / 182.461, JP-A 05 / 201.946, JP-A 05 / 255.012, JP-A 05 / 294.948, JP-A 06 / 087,842, JP-A 06 / 184,127, JP-A 07 / 025,840, JP-A 07 / 224,041, JP-A 08 / 012,648, JP-A 08 / 027,133, JP-A 08 / 127,563, DE Note No. 19 528 651,
DE Anm. Nr. 19 534 492, DE Anm. Nr. 19 540 361, DE Anm. Nr. 19 541 382 und DE Anm. Nr. 19 618 852;DE note no. 19 534 492, DE note no. 19 540 361, DE note no. 19 541 382 and DE note no. 19 618 852;
besonders bevorzugte Wirkstoffe des Typs IA, in denen R' für -C[C02CH3] =CHCH3 oder -C [C02CH3] =CHCHCH3 steht, entsprechen im allgemeinen und im besonderen den in den folgenden Schriften beschriebenen Verbindungen: EP-A 280 185, EP-A 463 488, EP-A 501 901, EP-A 513 580, EP-A 515 901, EP-A 621 277, EP-A 627 411, EP-A 647 631, EP-A 669 319, EP-A 673 923, EP-A 684 226, WO-A 95/21,153, WO-A 95/29,896, WO-A 96/16,943, WO-A 96/22,983, WO-A 96/35,690, WO-A 96/37,480, WO-A 97/01,545, JP-A 07/224,041, DE Anm. Nr. 19 528 651, DE Anm. Nr. 19 534 492, DE Anm. Nr. 19 540 361, DE Anm. Nr. 19 541 382 und DE Anm. Nr. 19 618 852;Particularly preferred active substances of type IA, in which R 'represents -C [CO 2 CH 3 ] = CHCH 3 or -C [CO 2 CH 3 ] = CHCHCH 3 , correspond in general and in particular to the compounds described in the following documents : EP-A 280 185, EP-A 463 488, EP-A 501 901, EP-A 513 580, EP-A 515 901, EP-A 621 277, EP-A 627 411, EP-A 647 631, EP -A 669 319, EP-A 673 923, EP-A 684 226, WO-A 95 / 21,153, WO-A 95 / 29,896, WO-A 96 / 16,943, WO-A 96 / 22,983, WO-A 96 / 35,690, WO-A 96 / 37,480, WO-A 97 / 01,545, JP-A 07 / 224,041, DE Application No. 19 528 651, DE Application No. 19 534 492, DE Application No. 19 540 361, DE note no. 19 541 382 and DE note no. 19 618 852;
besonders bevorzugte Wirkstoffe des Typs IA, in denen R' für -C [COCH3] =NOCH3 oder -C [COCH2CH3] =NOCH3 steht, entsprechen im allgemeinen und im besonderen den in der EP-A 498 188, WO-A 96/22,983, WO-A 96/31,463 und WO-A 96/35,690 beschriebenen Verbindungen;Particularly preferred active substances of type IA, in which R 'represents -C [COCH 3 ] = NOCH 3 or -C [COCH 2 CH 3 ] = NOCH 3 , correspond in general and in particular to those in EP-A 498 188, Compounds described in WO-A 96 / 22,983, WO-A 96 / 31,463 and WO-A 96 / 35,690;
besonders bevorzugte Wirkstoffe des Typs IA, in denen R' für -N(OCH3)C02CH3, -N(CH3)-C02CH3 oder -N(CH2CH3) -C02CH3 steht, entsprechen im allgemeinen und im besonderen den in den folgenden Schriften beschriebenen Verbindungen: EP-A 498 396, EP-A 619particularly preferred active substances of type IA, in which R 'represents -N (OCH 3 ) C0 2 CH 3 , -N (CH 3 ) -C0 2 CH 3 or -N (CH 2 CH 3 ) -C0 2 CH 3 , correspond in general and in particular to the compounds described in the following documents: EP-A 498 396, EP-A 619
301, EP-A 658 547, EP-A 704 430, WO-A 93/15,046, WO-A 96/01,256, WO-A 96/01,258, WO-A 96/16,029, WO-A 96/16,030, WO-A 96/16,044, WO-A 96/17,851, WO-A 96/22,983, WO-A 96/35,690, WO-A 97/01,544, JP-A 06/025,142, JP-A 06/056,756, JP-A 06/271,525, JP-A 07/145,137, JP-A 07/278,090, JP-A 08/188,565 und DE Anm. Nr. 19 618 852.301, EP-A 658 547, EP-A 704 430, WO-A 93 / 15,046, WO-A 96 / 01,256, WO-A 96 / 01,258, WO-A 96 / 16,029, WO-A 96 / 16,030, WO -A 96 / 16,044, WO-A 96 / 17,851, WO-A 96 / 22,983, WO-A 96 / 35,690, WO-A 97 / 01,544, JP-A 06 / 025,142, JP-A 06 / 056,756, JP- A 06 / 271,525, JP-A 07 / 145,137, JP-A 07 / 278,090, JP-A 08 / 188,565 and DE Note No. 19 618 852.
Besonders bevorzugte Wirkstoffe des Typs IB, in denen Rx für -OC [CO2CH3] =CHOCH3, -OC [C02CH3] =CHCH3, -OC [C02CH3] =CHCH2CH3 , -SC[C02CH3]=CH0CH3, -SC [C02CH3] =CHCH3 , -SC [C02CH3] =CHCH2CH3 , -N(CH3)C[C02CH3]=CHOCH3, -N(CH3)C [C02CH3] =NOCH3 , -CH2C [C02CH3] =CHOCH3 , -CH2C [C02CH3] =NOCH3 oder CH2C [CONHCH3] =NOCH3 steht, entsprechen im allgemeinen und im besonderen den in den folgenden Schriften beschriebenen Verbindungen: EP-A 212 859, EP-A 331 966, EP-A 383 117, EP-A 384 211, EP-A 389 901, EP-A 409 369, EP-A 464 381, EP-A 471 261, EP-A 503 436, EP-A 546 387, EP-A 548 650, EP-A 579 908, EP-A 584 625, WO-A 96/22,983, WO-A 96/32,399, WO-A 96/35,669 und JP-A 07/330,735.Particularly preferred active substances of type IB, in which R x for -OC [CO 2 CH 3 ] = CHOCH 3 , -OC [C0 2 CH 3 ] = CHCH 3 , -OC [C0 2 CH 3 ] = CHCH 2 CH 3 , -SC [C0 2 CH 3 ] = CH0CH 3 , -SC [C0 2 CH 3 ] = CHCH 3 , -SC [C0 2 CH 3 ] = CHCH 2 CH 3 , -N (CH 3 ) C [C0 2 CH 3 ] = CHOCH 3 , -N (CH 3 ) C [CO 2 CH 3 ] = NOCH 3 , -CH 2 C [CO 2 CH 3 ] = CHOCH 3 , -CH 2 C [CO 2 CH 3 ] = NOCH 3 or CH 2 C [CONHCH 3 ] = STILL 3 stands in general and in particular correspond to the compounds described in the following documents: EP-A 212 859, EP-A 331 966, EP-A 383 117, EP-A 384 211, EP-A 389 901, EP-A 409 369, EP-A 464 381, EP-A 471 261, EP-A 503 436, EP-A 546 387, EP-A 548 650, EP-A 579 908, EP-A 584 625, WO-A 96 / 22,983 , WO-A 96 / 32,399, WO-A 96 / 35,669 and JP-A 07 / 330,735.
Beispiele für insbesondere geeignete Wirkstoffe des Typs I sind in den folgenden Tabellen zusammengestellt.Examples of particularly suitable type I active substances are compiled in the following tables.
Tabelle I . IATable I. IA
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(C0CH3)=CHOCH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het) aryl-oxymethylen steht, wobei die ggf. subst. (Het)aryl- gruppe die folgende Bedeutung hatCompounds of the formula IA, in which Q is phenyl, R 'is -C (C0CH 3 ) = CHOCH 3 , n is 0, R "is optionally substituted (het) aryloxymethylene, the optionally subst. (Het) aryl group has the following meaning
Figure imgf000011_0001
Figure imgf000011_0001
Tabelle I . IBTable I. IB
Verbindungen der Formel IA, in denen R' für -C (C02CH3) =CHOCH3 steht, Q Phenyl bedeutet, n den Wert 0 hat, R" für ggf. subst. (Het) aryl-oxy steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hatCompounds of the formula IA, in which R 'is -C (C0 2 CH 3 ) = CHOCH 3 , Q is phenyl, n is 0, R "is optionally substituted (het) aryloxy, where the optionally subst. (het) aryl group has the following meaning
Figure imgf000011_0002
Tabelle I . IC
Figure imgf000011_0002
Table I. IC
Verbindungen der Formel IA, in denen R' für -C (C02CH3) =CHOCH3 steht, Q Phenyl bedeutet, n den Wert 0 hat, R" für ggf. subst. (Het) aryl-ethenylen steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hatCompounds of the formula IA, in which R 'is -C (C0 2 CH 3 ) = CHOCH 3 , Q is phenyl, n is 0, R "is optionally substituted. (Het) aryl-ethenylene, the optionally subst. (het) aryl group has the following meaning
Nr. ggf. subst. (Het)aryl LiteraturNo. if necessary subst. (Het) aryl literature
I.1C-1 1- (2 , 4-Cl2-C6H3) , 5-CF3-pyrazol-4-yl EP-A 528 245I.1C-1 1- (2, 4-Cl 2 -C 6 H 3 ), 5-CF 3 -pyrazol-4-yl EP-A 528 245
I.1C-2 1- (4-Cl-C6H4) -pyrazol-4-yl EP-A 378 755I.1C-2 1- (4-Cl-C 6 H 4 ) -pyrazol-4-yl EP-A 378 755
I.1C-3 3-CF3-C6H4 EP-A 203 606I.1C-3 3-CF 3 -C 6 H 4 EP-A 203 606
I.1C-4 3-Cl-C6H4 EP-A 203 606I.1C-4 3-Cl-C 6 H 4 EP-A 203 606
I.1C-5 4-C6H5-C6H4 EP-A 203 606I.1C-5 4-C 6 H 5 -C 6 H 4 EP-A 203 606
I.1C-6 l-(3-CH3-C6H4) , 5-Cl-pyrazol-4-yl EP-A 528 245I.1C-6 l- (3-CH 3 -C 6 H 4 ), 5-Cl-pyrazol-4-yl EP-A 528 245
I.1C-7 l-(4-CH3-C6H4) , 5-Cl-pyrazol-4-yl EP-A 528 245I.1C-7 l- (4-CH 3 -C 6 H 4 ), 5-Cl-pyrazol-4-yl EP-A 528 245
I.1C-8 l-(3-Cl-C6H4) , 5-Cl-pyrazol-4-yl EP-A 528 245I.1C-8 l- (3-Cl-C 6 H 4 ), 5-Cl-pyrazol-4-yl EP-A 528 245
I.1C-9 l-(4-Cl-C6H4) , 5-Cl-pyrazol-4-yl EP-A 528 245I.1C-9 l- (4-Cl-C 6 H 4 ), 5-Cl-pyrazol-4-yl EP-A 528 245
Tabelle I .1DTable I .1D
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(C02CH3)=CHOCH3 steht, n den Wert 0 hat, R" für CH2ON=CRαRß steht, wobei Rα und R" die folgende Bedeutung habenCompounds of the formula IA, in which Q is phenyl, R 'is -C (C0 2 CH 3 ) = CHOCH 3 , n is 0, R "is CH 2 ON = CR α R ß , where R α and R "have the following meaning
Figure imgf000012_0001
Figure imgf000012_0001
Tabelle I.1ETable I.1E
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(C02CH3)=CHOCH3 steht, n den Wert 0 hat, R" fürCompounds of the formula IA, in which Q is phenyl, R 'is -C (C0 2 CH 3 ) = CHOCH 3 , n is 0, R "is
CH2ON=CRγCRδ=NORε steht, wobei Rγ, Rδ und Rε die folgende Bedeutung habenCH 2 ON = CR γ CR δ = NOR ε , where R γ , R δ and R ε have the following meaning
Figure imgf000012_0002
Figure imgf000012_0002
Figure imgf000013_0001
Figure imgf000013_0001
Tabelle I.2ATable I.2A
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(C02CH3)=NOCH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het) aryl-oxymethylen steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hatCompounds of the formula IA, in which Q is phenyl, R 'is -C (C0 2 CH 3 ) = NOCH 3 , n is 0, R "is optionally substituted (het) aryl-oxymethylene, the optionally subst. (het) aryl group has the following meaning
Figure imgf000013_0002
Figure imgf000013_0002
Tabelle I.2BTable I.2B
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C (Cθ2CH3)=NOCH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het) aryl-oxy steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hatCompounds of the formula IA, in which Q is phenyl, R 'is -C (CO 2 CH 3 ) = NOCH 3 , n is 0, R "is optionally substituted. (Het) aryloxy, where the optionally subst. (het) aryl group has the following meaning
Figure imgf000013_0003
Figure imgf000014_0001
Tabelle I . 2C
Figure imgf000013_0003
Figure imgf000014_0001
Table I. 2C
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C (C0CH3)=NOCH3 steht, n den Wert 0 hat, R" für CH2ON=CRαRß steht, wobei Rα und RP die folgende Bedeutung habenCompounds of formula IA where Q is phenyl, R 'is -C (C0CH 3 ) = NOCH 3 , n is 0, R "is CH 2 ON = CR α Rß, where R α and RP are the following Have meaning
Figure imgf000014_0002
Figure imgf000014_0002
Tabelle I.2DTable I.2D
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(C02CH3)=NOCH3 steht, n den Wert 0 hat, R" für CH2ON=CRγCRδ=NORε steht, wobei Rγ, Rδ und Rε die folgende Bedeutung habenCompounds of the formula IA, in which Q is phenyl, R 'is -C (C0 2 CH 3 ) = NOCH 3 , n is 0, R "is CH 2 ON = CR γ CR δ = NOR ε , where Rγ, R δ and R ε have the following meaning
Figure imgf000014_0003
Figure imgf000015_0001
Tabelle I .3A
Figure imgf000014_0003
Figure imgf000015_0001
Table I .3A
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(CONHCH3)=NOCH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het) aryl-oxymethylen steht, wobei die ggf. subst. (Het)aryl- gruppe die folgende Bedeutung hatCompounds of the formula IA, in which Q is phenyl, R 'is -C (CONHCH 3 ) = NOCH 3 , n is 0, R "is optionally substituted (het) aryl-oxymethylene, the subst. (Het) aryl group has the following meaning
Nr. ggf. subst. (Het)aryl LiteraturNo. if necessary subst. (Het) aryl literature
I.3A-1 2-CH3-C6H4 EP-A 477 631I.3A-1 2-CH 3 -C 6 H 4 EP-A 477 631
I.3A-2 2,5-(CH3)2-C6H3 EP-A 477 631I.3A-2 2.5- (CH 3 ) 2 -C 6 H 3 EP-A 477 631
I.3A-3 2,4-(CH3)2-C6H3 EP-A 477 631I.3A-3 2,4- (CH 3 ) 2 -C 6 H 3 EP-A 477 631
I.3A-4 2,3,5-(CH3)3-C6H2 EP-A 477 631I.3A-4 2,3,5- (CH 3 ) 3 -C 6 H 2 EP-A 477 631
I.3A-5 2-CH3, 4-C[CH3]=NOCH3-C6H3 EP-A 579 124I.3A-5 2-CH 3 , 4-C [CH 3 ] = NOCH 3 -C 6 H 3 EP-A 579 124
I.3A-6 1- [4-Cl-C6H4] -pyrazol-3-yl WO-A 94/19,331I.3A-6 1- [4-Cl-C 6 H 4 ] pyrazol-3-yl WO-A 94 / 19,331
I.3A-7 1- [2 , 4-Cl2-C6H3] -pyrazol-3-yl WO-A 94/19,331I.3A-7 1- [2,4-Cl 2 -C 6 H 3 ] pyrazol-3-yl WO-A 94 / 19,331
I.3A-8 3-C1, 5-CF3-pyridin-2-yl JP-A 04/182,461I.3A-8 3-C1, 5-CF 3 -pyridin-2-yl JP-A 04 / 182,461
I.3A-9 3 , 5-Cl2-pyridin-2-yl JP-A 04/182,461I.3A-9 3, 5-Cl 2 -pyridin-2-yl JP-A 04 / 182,461
I.3A-10 3-CF3, 6-Cl-pyridin-2-yl JP-A 04/182,461I.3A-10 3-CF 3 , 6-Cl-pyridin-2-yl JP-A 04 / 182,461
I.3A-11 2-Cl-C6H EP-A 477 631I.3A-11 2-Cl-C 6 H EP-A 477 631
I.3A-12 2-CF3-C6H4 EP-A 477 631I.3A-12 2-CF 3 -C 6 H 4 EP-A 477 631
I.3A-13 2,4-Cl2-C6H3 EP-A 477 631I.3A-13 2,4-Cl 2 -C 6 H 3 EP-A 477 631
I.3A-14 2,5-Cl2-C6H3 EP-A 477 631I.3A-14 2,5-Cl 2 -C 6 H 3 EP-A 477 631
I.3A-15 4- [2-Cl-C6H4] -thiazol-2-yl WO-A 94/19,331I.3A-15 4- [2-Cl-C 6 H 4 ] -thiazol-2-yl WO-A 94 / 19,331
I.3A-16 4- [2-F-C6H4] -thiazol-2-yl WO-A 94/19,331I.3A-16 4- [2-FC 6 H 4 ] thiazol-2-yl WO-A 94 / 19,331
I.3A-17 4- [2-CH3-C6H ] -thiazol-2-yl WO-A 94/19,331I.3A-17 4- [2-CH 3 -C 6 H] -thiazol-2-yl WO-A 94 / 19,331
I.3A-18 1- [4-F-C6H4] -pyrazol-3-yl WO-A 94/19,331I.3A-18 1- [4-FC 6 H 4 ] pyrazol-3-yl WO-A 94 / 19,331
I.3A-19 1- [2 , 4-F2-C6H3] -pyrazol-3-yl WO-A 94/19,331I.3A-19 1- [2, 4-F 2 -C 6 H 3 ] pyrazol-3-yl WO-A 94 / 19,331
Tabelle I.3BTable I.3B
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(CONHCH3)=NOCH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het) aryl-oxy steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hatCompounds of the formula IA, in which Q is phenyl, R 'is -C (CONHCH 3 ) = NOCH 3 , n is 0, R "is optionally substituted (het) aryloxy, the optionally subst. (Het) aryl group has the following meaning
Figure imgf000015_0002
Tabelle I . 3C
Figure imgf000015_0002
Table I. 3C
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(CONHCH3)=NOCH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het) aryl-ethenylen steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hatCompounds of the formula IA, in which Q is phenyl, R 'is -C (CONHCH 3 ) = NOCH 3 , n is 0, R "is optionally substituted (het) aryl-ethenylene, the optionally subst. (Het) aryl group has the following meaning
Figure imgf000016_0001
Tabelle I.3D
Figure imgf000016_0001
Table I.3D
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(CONHCH3)=NOCH3 steht, n den Wert 0 hat, R" für CH2ON=CRRß steht, wobei Rα und RP die folgende Bedeutung habenCompounds of the formula IA in which Q is phenyl, R 'is -C (CONHCH 3 ) = NOCH 3 , n is 0, R "is CH 2 ON = CRRß, where R α and RP have the following meanings
Figure imgf000016_0002
Figure imgf000016_0002
Tabelle I.3ETable I.3E
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(CONHCH3)=NOCH3 steht, n den Wert 0 hat, R" fürCompounds of the formula IA where Q is phenyl, R 'is -C (CONHCH 3 ) = NOCH 3 , n is 0, R "is
CH2ON=CRγCRδ=NORε steht, wobei Rγ, Rδ und Rε die folgende Bedeutung habenCH 2 ON = CR γ CR δ = NOR ε , where R γ , R δ and R ε have the following meaning
Figure imgf000016_0003
Figure imgf000016_0003
Figure imgf000017_0001
Figure imgf000017_0001
Tabelle I.4ATable I.4A
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(C02CH3)=CHCH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het) aryl-oxymethylen steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hatCompounds of the formula IA, in which Q is phenyl, R 'is -C (C0 2 CH 3 ) = CHCH 3 , n is 0, R "is optionally substituted. (Het) aryl-oxymethylene, the optionally subst. (het) aryl group has the following meaning
Figure imgf000017_0002
Figure imgf000017_0002
Tabelle I .4BTable I .4B
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(C02CH3)=CHCH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het) aryl-oxy steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hatCompounds of the formula IA, in which Q is phenyl, R 'is -C (C0 2 CH 3 ) = CHCH 3 , n is 0, R "is optionally substituted. (Het) aryloxy, where the optionally subst. (het) aryl group has the following meaning
Figure imgf000017_0003
Figure imgf000018_0001
Figure imgf000017_0003
Figure imgf000018_0001
Tabelle I . 4CTable I. 4C
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(C02CH3)=CHCH3 steht, n den Wert 0 hat, R" für CH2ON=CRγCRδ=NORε steht, wobei Rγ, R und Rε die folgende Bedeutung habenCompounds of the formula IA, in which Q is phenyl, R 'is -C (C0 2 CH 3 ) = CHCH 3 , n is 0, R "is CH 2 ON = CR γ CR δ = NOR ε , where R γ , R and R ε have the following meaning
Figure imgf000018_0002
Figure imgf000018_0002
Tabelle I.5ATable I.5A
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' fürCompounds of the formula IA, in which Q is phenyl, R 'for
-C(C02CH3)=CHCH2CH3 steht, n den Wert 0 hat, R" für ggf. subst.-C (C0 2 CH 3 ) = CHCH 2 CH 3 , n has the value 0, R "for optionally subst.
(Het) aryl-oxymethylen steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hat(Het) aryl-oxymethylene, where the subst. (Het) aryl group has the following meaning
Figure imgf000018_0003
Figure imgf000018_0003
Figure imgf000019_0001
Figure imgf000019_0001
Tabelle I . 5BTable I. 5B
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(C02CH3)=CHCH2CH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het) aryl-oxy steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hatCompounds of the formula IA, in which Q is phenyl, R 'is -C (C0 2 CH 3 ) = CHCH 2 CH 3 , n is 0, R "is optionally substituted (het) aryloxy, where the optionally substituted (het) aryl group has the following meaning
Figure imgf000019_0002
Figure imgf000019_0002
Tabelle I.5CTable I.5C
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(C02CH3)=CHCH2CH3 steht, n den Wert 0 hat, R" fürCompounds of the formula IA, in which Q is phenyl, R 'is -C (C0 2 CH 3 ) = CHCH 2 CH 3 , n is 0, R "is
CH2ON=CRγCRδ=NORε steht, wobei Rγ, Rδ und Rε die folgende Bedeutung habenCH 2 ON = CR γ CR δ = NOR ε , where R γ , R δ and R ε have the following meaning
Figure imgf000019_0003
Tabelle 1 . 6A
Figure imgf000019_0003
Table 1 . 6A
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(COCH3)=NOCH3 steht, n den Wert 0 hat, R" für ggf. subst, (Het) aryl-oxymethylen steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hatCompounds of the formula IA, in which Q is phenyl, R 'is -C (COCH 3 ) = NOCH 3 , n is 0, R "is optionally subst, (het) aryl-oxymethylene, the subst. (Het) aryl group has the following meaning
Figure imgf000020_0001
Figure imgf000020_0001
Tabelle I.6BTable I.6B
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(COCH3)=NOCH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het) aryl-oxy steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hatCompounds of the formula IA, in which Q is phenyl, R 'is -C (COCH 3 ) = NOCH 3 , n is 0, R "is optionally substituted (het) aryloxy, the optionally subst. (Het) aryl group has the following meaning
Figure imgf000020_0002
Figure imgf000020_0002
Tabelle I .7ATable I .7A
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(C0CH2CH3)=N0CH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het) aryl-oxymethylen steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hatCompounds of the formula IA, in which Q is phenyl, R 'is -C (COCH 2 CH 3 ) = NOCH 3 , n is 0, R "is optionally substituted (het) aryl oxymethylene, the optionally subst. (het) aryl group has the following meaning
Figure imgf000020_0003
Figure imgf000020_0003
Figure imgf000021_0001
Figure imgf000021_0001
Tabelle I.7BTable I.7B
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -C(COCH2CH3)=NOCH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het) aryl-oxy steht, wobei die ggf. subst. (Het) arylgruppe die folgende Bedeutung hatCompounds of the formula IA, in which Q is phenyl, R 'is -C (COCH 2 CH 3 ) = NOCH 3 , n is 0, R "is optionally substituted. (Het) aryloxy, where the optionally subst. (het) aryl group has the following meaning
Figure imgf000021_0002
Figure imgf000021_0002
Tabelle I .8ATable I .8A
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -N(OCH3)-C02CH3 steht, n den Wert 0 hat, R" für ggf. subst. (Het) aryl-oxymethylen steht, wobei die ggf. subst. (Het)aryl- gruppe die folgende Bedeutung hatCompounds of the formula IA, in which Q is phenyl, R 'is -N (OCH 3 ) -C0 2 CH 3 , n is 0, R "is optionally substituted (Het) aryl-oxymethylene, the optionally subst. (het) aryl group has the following meaning
Figure imgf000021_0003
Figure imgf000022_0001
Figure imgf000021_0003
Figure imgf000022_0001
Tabelle I . 8BTable I. 8B
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -N(OCH3) -C02CH3 steht, n den Wert 0 hat, R" für CH2ON=CRRP steht, wobei Rα und RP die folgende Bedeutung habenCompounds of formula IA where Q is phenyl, R 'is -N (OCH 3 ) -C0 2 CH 3 , n is 0, R "is CH 2 ON = CRRP, where R α and RP are the following Have meaning
Figure imgf000022_0002
Tabelle I .8C
Figure imgf000022_0002
Table I .8C
Verbindungen der Formel IA, in denen Q Phenyl bedeutet, R' für -N(OCH3) -C02CH3 steht, n den Wert 0 hat und R" für CH2ON=CRγCRδ=NORε steht, wobei Rγ, Rδ und Rε die folgende Bedeutung habenCompounds of the formula IA, in which Q is phenyl, R 'is -N (OCH 3 ) -C0 2 CH 3 , n is 0 and R "is CH 2 ON = CR γ CR δ = NOR ε , where R γ , R δ and R ε have the following meaning
Figure imgf000022_0003
Figure imgf000023_0001
Figure imgf000022_0003
Figure imgf000023_0001
Bevorzugt setzt man bei der Bereitstellung der Mischungen die reinen Wirkstoffe IA bzw. IB und II ein, denen man je nach Bedarf weitere Wirkstoffe gegen Schädlinge (z.B. Insekten, Spinntiere oder Nematoden) oder Schadpilze oder auch herbizide oder wachstumsregulierende Wirkstoffe oder Düngemittel beimischen kann.When preparing the mixtures, preference is given to using the pure active ingredients IA or IB and II, to which, as required, further active ingredients can be added to combat pests (e.g. insects, arachnids or nematodes) or harmful fungi or else herbicidal or growth-regulating active ingredients or fertilizers.
Die Mischungen der Verbindungen IA bzw. IB und II bzw. die gleichzeitige gemeinsame oder getrennte Verwendung der Verbindungen IA und II oder IB und II zeichnen sich durch eine hervorragende Wirkung gegen ein breites Spektrum insbesondere von pflanzenpathogenen Pilzen aus. Sie sind z.T. systemisch wirksam (d.h. sie können bei der Anwendung zum Pflanzenschutz ohne Wirkungsverlust von der behandelten Pflanze aufgenommen und ggf. in der Pflanze transportiert werden) und können daher auch als Blatt- und Bodenfungizide eingesetzt werden.The mixtures of the compounds IA or IB and II or the simultaneous joint or separate use of the compounds IA and II or IB and II are distinguished by an excellent action against a broad spectrum, in particular of phytopathogenic fungi. They are partly systemically effective (i.e. when used for crop protection, they can be absorbed by the treated plant without loss of activity and possibly transported in the plant) and can therefore also be used as leaf and soil fungicides.
Besondere Bedeutung haben sie für die Bekämpfung einer Vielzahl von Pilzen an verschiedenen Kulturpflanzen wie Baumwolle, Gemüsepflanzen (z.B. Gurken, Bohnen und Kürbisgewächse), Gerste, Gras, Hafer, Kaffee, Mais, Obstpflanzen, Reis, Roggen, Soja, Wein, Weizen, Zierpflanzen, Zuckerrohr und einer Vielzahl von Samen.They are particularly important for combating a large number of fungi on various crops such as cotton, vegetables (e.g. cucumber, beans and squashes), barley, grass, oats, coffee, corn, fruit plants, rice, rye, soy, wine, wheat, ornamental plants , Sugar cane and a variety of seeds.
Speziell eignen sie sich zur Bekämpfung folgender Pflanzenkrankheiten:They are particularly suitable for combating the following plant diseases:
Alteri-aria-Arten an Gemüse und Obst,Alteri aria types of vegetables and fruits,
Botrytis cinerea (Grauschimmel) an Erdbeeren, Gemüse, Zierpflanzen und Reben,Botrytis cinerea (gray mold) on strawberries, vegetables, ornamental plants and vines,
Cercospora arachidicola an Erdnüssen,Cercospora arachidicola on peanuts,
Erysiphe cichoracearum und Sphaerotheca fuliginea an Kürbisgewächsen,Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin plants,
Erysiphe graminis (echter Mehltau) an Getreide, Fusarium- und Verticillium-Arten an verschiedenen Pflanzen, Helmin thosporium-Arten an Getreide, Mycosptiaerella-Arten an Bananen,Erysiphe graminis (powdery mildew) on cereals, Fusarium and Verticillium species on various plants, Helmin thosporium species on cereals, Mycosptiaerella species on bananas,
Phytophthora infes tans an Kartoffeln und Tomaten, Plasmopara vi ticola an Reben, Podosphaera leucotricha an Äpfeln,Phytophthora infes tans on potatoes and tomatoes, Plasmopara vi ticola on vines, Podosphaera leucotricha on apples,
Pseudocercosporella herpotrichoides an Weizen und Gerste, Pseudocercosporel la-Arten an Hopfen und Gurken, • Pseudoperonospora-Arten an Hopfen und Gurken,Pseudocercosporella herpotrichoides on wheat and barley, Pseudocercosporel la species on hops and cucumber, Pseudoperonospora species on hops and cucumbers,
• Puccinia-Arten an Getreide,Puccinia species on cereals,
• Pyricularia oryzae an Reis,Pyricularia oryzae on rice,
• R izoctonia-Arten an Baumwolle, Reis und Rasen, • Septoria nodorum an Weizen,R izoctonia species on cotton, rice and lawn, Septoria nodorum on wheat,
• Uncinula neca tor an Reben,• Uncinula neca tor on vines,
• [/sfcilago-Arten an Getreide und Zuckerrohr, sowie• [/ sfcilago species on cereals and sugar cane, as well
• Ven turia inaequalis (Schorf) an Äpfeln.• Ven turia inaequalis (scab) on apples.
Die erfindungsgemäßen Mischungen eignen sich außerdem zur Bekämpfung von Schadpilzen wie Paecilomyces variotii im Material - schütz (z.B. Holz, Papier, Dispersionen für den Ansprich, Fasern bzw. Gewebe) und im Vorratsschutz.The mixtures according to the invention are also suitable for combating harmful fungi such as Paecilomyces variotii in the protection of materials (e.g. wood, paper, dispersions for addressing, fibers or fabrics) and in the protection of stored goods.
Die Verbindungen IA bzw. IB und II und/oder III können gleichzeitig, und zwar gemeinsam oder getrennt oder nacheinander aufgebracht werden, wobei die Reihenfolge bei getrennter Applikation im allgemeinen keine Auswirkung auf den Bekämpfungserfolg hat.The compounds IA or IB and II and / or III can be applied simultaneously, that is together or separately or in succession, the sequence in the case of separate application generally not having any effect on the success of the control measures.
Die Verbindungen IA und II bzw. IB und II werden üblicherweise in einem Gewichtsverhältnis von 10 : 1 bis 0,1 : 1, vorzugsweise 5 : 1 bis 0,2 : 1, insbesondere 2 : 1 bis 0,5 : 1 (IA:II bzw. IB:II) angewendet.The compounds IA and II or IB and II are usually in a weight ratio of 10: 1 to 0.1: 1, preferably 5: 1 to 0.2: 1, in particular 2: 1 to 0.5: 1 (IA: II or IB: II) applied.
Die Verbindungen IA bzw. IB und III werden üblicherweise in einem Gewichtsverhältnis von 25 : 1 bis 0,25 : 1, vorzugsweiseThe compounds IA or IB and III are usually in a weight ratio of 25: 1 to 0.25: 1, preferably
20 : 1 bis 0,5 : 1, insbesondere 15 : 1 bis 0,75 : 1 (IA:III bzw. IB:III) angewendet.20: 1 to 0.5: 1, in particular 15: 1 to 0.75: 1 (IA: III or IB: III) applied.
Die Verbindungen IA bzw. IB und II und III werden üblicherweise in einem Gewichtsverhältnis von 10 : 1 : 0,4 bis 0,1 : 1 : 0,4, vorzugsweise 5 : 1 : 0,4 bis 0,2 : 1 : 0,4, insbesondere 2 : 1 : 0,4 bis 0,5 : 1 : 0,4 (IA:II:III bzw. IB:II:III), angewendet.The compounds IA or IB and II and III are usually in a weight ratio of 10: 1: 0.4 to 0.1: 1: 0.4, preferably 5: 1: 0.4 to 0.2: 1: 0 , 4, in particular 2: 1: 0.4 to 0.5: 1: 0.4 (IA: II: III or IB: II: III), applied.
Die Aufwandmengen der erfindungsgemäßen Mischungen liegen bei der Verwendung zum Schutz von Kulturpflanzen je nach der Art des gewünschten Effektes bei 2 bis 0,1 kg/ha, vorzugsweise 1,25 bis 0,2 kg/ha, insbesondere 0,75 bis 0,3 kg/ha.When used to protect crop plants, the application rates of the mixtures according to the invention are from 2 to 0.1 kg / ha, preferably from 1.25 to 0.2 kg / ha, in particular from 0.75 to 0.3, depending on the type of effect desired kg / ha.
Die Aufwandmengen liegen dabei für die Verbindungen IA und IB bei 1 bis 0,01 kg/ha, vorzugsweise 0,5 bis 0,02 kg/ha, insbesondere 0,25 bis 0,03 kg/ha. Die Aufwandmengen für die Verbindungen II liegen im allgemeinen bei 0,5 bis 0,001 kg/ha, vorzugsweise 0,25 bis 0,005 kg/ha, insbesondere 0,1 bis 0,01 kg/ha.The application rates for the compounds IA and IB are 1 to 0.01 kg / ha, preferably 0.5 to 0.02 kg / ha, in particular 0.25 to 0.03 kg / ha. The application rates for the compounds II are generally from 0.5 to 0.001 kg / ha, preferably 0.25 to 0.005 kg / ha, in particular 0.1 to 0.01 kg / ha.
Die Aufwandmengen für die Verbindung III liegen im allgemeinen bei 0,001 bis 0,3 kg/ha, vorzugsweise 0,005 bis 0,2 kg/ha, ins¬ besondere 0,01 bis 0,1 kg/ha.The application rates for the compound III are in general from 0.001 to 0.3 kg / ha, preferably 0.005 to 0.2 kg / ha, into ¬ particular 0.01 to 0.1 kg / ha.
Die Mischungsverhältnisse bezüglich der Verbindungen II und III liegen im allgemeinen bei 4 : 1, vorzugsweise 3 : 1, insbesondere 2,5 : 1 (II:III) .The mixing ratios with respect to the compounds II and III are generally 4: 1, preferably 3: 1, in particular 2.5: 1 (II: III).
Bei der Saatgutbehandlung werden im allgemeinen Aufwandmengen an Mischung von 0,1 bis 100 g/lOOkg Saatgut, vorzugsweise 0,5 bis 50 g/lOOkg Saatgut, insbesondere 1 bis 10 g/lOOkg Saatgut verwendet .In the case of seed treatment, application rates of mixture of 0.1 to 100 g / 100 kg of seed, preferably 0.5 to 50 g / 100 kg of seed, in particular 1 to 10 g / 100 kg of seed, are generally used.
Die Aufwandmengen der erfindungsgemäßen Mischungen liegen bei der Verwendung zum Schutz von Materialien oder Räumen je nach der Art des gewünschten Effektes bei 0,01 bis 20 g/m3, vorzugsweise 0,05 bis 10 g/m3, insbesondere 0,1 bis 5 g/m3.When used to protect materials or spaces, the application rates of the mixtures according to the invention are from 0.01 to 20 g / m 3 , preferably 0.05 to 10 g / m 3 , in particular 0.1 to 5, depending on the type of effect desired g / m 3 .
Sofern für Pflanzen pathogene Schadpilze zu bekämpfen sind erfolgt die gemeinsame oder getrennte Applikation der Verbindungen IA bzw. IB und II und/oder III oder der Mischungen aus den Verbindungen IA bzw. IB und II und/oder III durch Besprühen oder Bestäuben der Samen, der Pflanzen oder der Böden vor oder nach der Aussaat der Pflanzen oder vor oder nach dem Keimen der Pflanzen.If pathogenic harmful fungi are to be combated for plants, the compounds IA or IB and II and / or III or the mixtures of the compounds IA or IB and II and / or III are applied jointly or separately by spraying or dusting the seeds, the Plants or the soil before or after sowing the plants or before or after the plants germinate.
Die erfindungsgemäßen fungiziden synergistischen Mischungen bzw. die Verbindungen IA bzw. IB und II und/oder III können beispielsweise in Form von direkt versprühbaren Lösungen, Pulver und Suspensionen oder in Form von hochprozentigen wäßrigen, öligen oder sonstigen Suspensionen, Dispersionen, Emulsionen, Öldispersionen, Pasten, Stäubemitteln, Streumitteln oder Granulaten aufbereitet und durch Versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen angewendet werden. Die Anwendungsform ist abhängig vom Verwendungszweck; sie soll in jedem Fall eine mög- liehst feine und gleichmäßige Verteilung der erfindungsgemäßen Mischung gewährleisten.The fungicidal synergistic mixtures according to the invention or the compounds IA or IB and II and / or III can be used, for example, in the form of directly sprayable solutions, powders and suspensions or in the form of high-strength aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, pastes , Dusts, scattering agents or granules are prepared and applied by spraying, atomizing, dusting, scattering or pouring. The form of application depends on the intended use; in any case, it should ensure as fine and uniform a distribution of the mixture according to the invention as possible.
Die Formulierungen werden in an sich bekannter Weise hergestellt, z.B. durch Zugabe von Lösungsmitteln und/oder Träger - Stoffen. Den Formulierungen werden üblicherweise inerte Zusatzstoffe wie Emulgiermittel oder Dispergiermittel beigemischt. Als oberflächenaktive Stoffe kommen die Alkali-, Erdalkali- und Ammoniumsalze von aromatischen Sulfonsäuren, z.B. Lignin-, Phenol-, Naphthalin- und Dibutylnaphthalinsulfonsäure, sowie von Fettsäure, Alkyl- und Alkylarylsulfonaten, Alkyl-, Laurylether- und Fettalkoholsulfaten, sowie Salze sulfatierter Hexa-, Hepta- und Octadecanole oder Fettalkoholglycolether, Kondensations - Produkte von sulfoniertem Naphthalin und seinen Derivaten mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxy- ethylenoctylphenolether, ethoxyliertes Isooctyl-, Octyl- oder Nonylphenol, Alkylphenol oder Tributylphenylpolyglycolether, Alkylarylpolyetheralkohole, Isotridecylalkohol, Fettalkohol - ethylenoxid-Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylen- alkylether oder Polyoxypropylen, Laurylalkoholpolyglycolether- acetat, Sorbitester, Lignin-Sulfitablaugen oder Methylcellulose in Betracht.The formulations are prepared in a manner known per se, for example by adding solvents and / or carriers. Inert additives such as emulsifiers or dispersants are usually added to the formulations. The surface-active substances are the alkali, alkaline earth and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acid, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa- , Hepta- and octadecanols or fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol ether, phenyl alcohol phenyl, phenol, phenyl, phenyl, phenyl, phenyl, phenyl, polyphenol, phenyl, phenyl, phenyl, phenyl, phenyl, alphenyl, phenyl, phenol , Isotridecyl alcohol, fatty alcohol - ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxypropylene, lauryl alcohol polyglycol ether acetate, sorbitol ester, lignin sulfite liquor or methyl cellulose.
Pulver, Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermählen der Verbindungen IA bzw. IB und II und/oder III oder der Mischungen aus den Verbindungen IA bzw. IB und II und/oder III mit einem festen Trägerstoff hergestellt werden.Powders, materials for broadcasting and dusts can be prepared by mixing or jointly grinding the compounds IA or IB and II and / or III or the mixtures of the compounds IA or IB and II and / or III with a solid carrier.
Granulate (z.B. Umhüllungs-, Imprägnierungs- oder Homogengranulate) werden üblicherweise durch Bindung des Wirkstoffs oder der Wirkstoffe an einen festen Trägerstoff hergestellt.Granules (e.g. coating, impregnation or homogeneous granules) are usually produced by binding the active ingredient or ingredients to a solid carrier.
Als Füllstoffe bzw. feste Trägerstoffe dienen beispielsweise Mineralerden wie Silicagel, Kieselsäuren, Kieselgele, Silikate, Talkum, Kaolin, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolo- mit, Diatomeenerde, Kalzium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, sowie Düngemittel wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver und andere feste Trägerstoffe.Mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics serve as fillers or solid carriers, for example. and fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
Die Formulierungen enthalten im allgemeinen 0,1 bis 95 Gew.-%, vorzugsweise 0,5 bis 90 Gew.- einer der Verbindungen IA bzw. IB oder II oder III oder der Mischung aus den Verbindungen IA bzw. IB und II und/oder III.The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of one of the compounds IA or IB or II or III or the mixture of the compounds IA or IB and II and / or III.
Die Wirkstoffe werden dabei in einer Reinheit von 90 % bisThe active ingredients are in a purity of 90% to
100 %, vorzugsweise 95 % bis 100 % (nach i-H-NMR- oder HPLC-Spek- trum) eingesetzt.100%, preferably 95% to 100% (according to i -H NMR or HPLC spectrum) is used.
Die Verbindungen IA, IB, II und III bzw. ihre Mischungen oder die entsprechenden Formulierungen werden angewendet, indem man die Schadpilze, ihren Lebensraum oder die vor Pilzbefall zu schützenden Materialien, Pflanzen, Samen, Böden, Flächen oder Räume mit einer fungizid wirksamen Menge der Mischung bzw. der Verbindungen IA bzw. IB und II und/oder III bei getrennter Ausbringung, behandelt. Die Behandlung kann vor oder nach dem Be- 5 fall durch die Schadpilze erfolgen.The compounds IA, IB, II and III or their mixtures or the corresponding formulations are used by adding the harmful fungi, their habitat or those prior to fungal attack protective materials, plants, seeds, soils, areas or spaces with a fungicidally effective amount of the mixture or of the compounds IA or IB and II and / or III treated separately. The treatment can be carried out before or after the 5 infection by the harmful fungi.
Die synergistische Wirkung der erfindungsgemäßen Mischungen ließ sich durch die folgenden Versuche zeigen:The following experiments demonstrated the synergistic effect of the mixtures according to the invention:
0 Anwendungsbeispiele zur synergistischen Wirkung der erfindungs- gemäßen Mischungen gegen Schadpilze0 Application examples for the synergistic effect of the mixtures according to the invention against harmful fungi
Die Wirkstoffe wurden getrennt oder gemeinsam als 10%ige Emulsion in einem Gemisch aus 67 Gew.-% Cyclohexanon und 23 Gew.-% 5 Emulgator aufbereitet und entsprechend der gewünschten Konzentration mit Wasser verdünnt.The active compounds were prepared separately or together as a 10% emulsion in a mixture of 67% by weight cyclohexanone and 23% by weight 5 emulsifier and diluted with water in accordance with the desired concentration.
Die Auswertung erfolgte durch Feststellung der befallenen Blattflächen in Prozent. Diese Prozent-Werte wurden in Wirkungs- 0 grade umgerechnet. Der Wirkungsgrad (W) wurde nach der Formel von Abbot wie folgt bestimmt:The evaluation was carried out by determining the affected leaf areas in percent. These percentages were converted into 0 degrees of effectiveness. Efficiency (W) was determined using Abbot's formula as follows:
W = (1 - α) -100/ß 5 α entspricht dem Pilzbefall der behandelten Pflanzen in % und ß entspricht dem Pilzbefall der unbehandelten (Kontroll-) Pflanzen in %W = (1 - α) -100 / ß 5 α corresponds to the fungal attack of the treated plants in% and ß corresponds to the fungal attack of the untreated (control) plants in%
Q Bei einem Wirkungsgrad von 0 entspricht der Befall der behandelten Pflanzen demjenigen der unbehandelten Kontrollpflanzen; bei einem Wirkungsgrad von 100 wiesen die behandelten Pflanzen keinen Befall auf. Q With an efficiency of 0, the infection of the treated plants corresponds to that of the untreated control plants; at an efficiency of 100, the treated plants showed no infection.
5 Die zu erwartenden Wirkungsgrade der Wirkstoffmischungen wurden nach der Colby Formel [R.S. Colby, Weeds 15., 20-22 (1967)] ermittelt und mit den beobachteten Wirkungsgraden verglichen.5 The expected efficacies of the active ingredient mixtures were determined using the Colby formula [RS Colby, Weeds 15 . , 20-22 (1967)] and compared with the observed efficiencies.
Colby Formel: E = x + y - x-y/100 0Colby formula: E = x + y - x-y / 100 0
E zu erwartender Wirkungsgrad, ausgedrückt in % der unbehandelten Kontrolle, beim Einsatz der Mischung aus den Wirkstoffen A und B in den Konzentrationen a und b x der Wirkungsgrad, ausgedrückt in % der unbehandelten Kon- 5 trolle, beim Einsatz des Wirkstoffs A in der Konzentration a y der Wirkungsgrad, ausgedrückt in % der unbehandelten Kontrolle, beim Einsatz des Wirkstoffs B in der Konzentration bE expected efficacy, expressed in% of the untreated control, when using the mixture of the active ingredients A and B at the concentrations a and bx efficacy, expressed in% of the untreated con- 5 control, when using active ingredient A at the concentration a y the efficiency, expressed in% of the untreated control, when using the active ingredient B in the concentration b
Beispiel 1 Wirksamkeit gegen Puccinia recondita an Weizen (Weizenbraunrost)Example 1 Activity against Puccinia recondita on Wheat (Wheat Brown Rust)
Blätter von in Töpfen gewachsenen Weizensämlingen der Sorte "Frühgold" wurden mit Sporen des Braunrostes (Puccinia recondita) bestäubt. Danach wurden die Töpfe für 24 Stunden in eine Kammer mit hoher Luftfeuchtigkeit (90 bis 95 %) und 20 bis 22°C gestellt. Während dieser Zeit keimten die Sporen aus und die Keimschläuche drangen in das Blattgewebe ein. Die infizierten Pflanzen wurden am nächsten Tag mit einer wäßrigen Wirkstoffauf - bereitung, die aus einer Stammlösung bestehend aus 10 % Wirk- stoff, 63 % Cyclohexanon und 27 % Emulgiermittel angesetzt wor¬ den war, tropfnaß besprüht. Nach dem Antrocknen des Spritz - belages wurden die Versuchspflanzen im Gewächshaus bei Temperaturen zwischen 20 und 22°C und 65 bis 70 % relativer Luftfeuchte für 7 Tage kultiviert. Dann wurde das Ausmaß der Rostpilzent- wicklung auf den Blättern ermittelt.Leaves of potted wheat seedlings of the "Frühgold" variety were dusted with spores of the brown rust (Puccinia recondita). The pots were then placed in a chamber with high air humidity (90 to 95%) and 20 to 22 ° C. for 24 hours. During this time, the spores germinated and the germ tubes penetrated the leaf tissue. The infected plants were on the next day with an aqueous Wirkstoffauf - preparation, the material consisting of 10% from a stock solution active ingredients, 63% of cyclohexanone and 27% emulsifier recognized wor ¬ was, until dripping wet. After the spray coating had dried on, the test plants were cultivated in a greenhouse at temperatures between 20 and 22 ° C. and 65 to 70% relative atmospheric humidity for 7 days. The extent of the rust fungus development on the leaves was then determined.
Die visuell ermittelten Werte für den Prozentanteil befallener Blattflächen wurden in Wirkungsgrade als % der unbehandelten Kontrolle umgerechnet. Wirkungsgrad 0 ist gleicher Befall wie in der unbehandelten Kontrolle, Wirkungsgrad 100 ist 0 % Befall. Die zu erwartenden Wirkungsgrade für Wirkstoffkombinationen wurden nach der Colby- Formel (Colby, S. R. (Calculating synergistic and antagonistic responses of herbicide Combinations" , Weeds, 15, S. 20 - 22, 1967)) ermittelt und mit den beobachteten Wir- kungsgraden verglichen.The visually determined values for the percentage of leaf areas affected were converted into efficiencies as% of the untreated control. Efficiency 0 is the same as in the untreated control, efficiency 100 is 0%. The expected efficacies for combinations of active ingredients were determined using the Colby formula (Colby, S.R. (Calculating synergistic and antagonistic responses of herbicide combinations ", Weeds, 15, pp. 20-22, 1967)) and compared with the observed efficacies.
Figure imgf000028_0001
Anwendungsbeispiel 1
Figure imgf000028_0001
Application example 1
Wirksamkeit gegen Puccinia reconditaEfficacy against Puccinia recondita
Fortsetzung 1Continued 1
Figure imgf000029_0001
Figure imgf000029_0001
*) berechnet nach der Colby- Formel*) calculated according to the Colby formula
Aus den Ergebnissen des Versuches geht hervor, daß der beobachteter Wirkungsgrad in allen Mischungsverhältnissen höher ist, als nach der Colby-Formel vorausberechnete Wirkungsgrad. The results of the experiment show that the observed efficiency in all mixing ratios is higher than the efficiency calculated in advance using the Colby formula.

Claims

Patentansprüche claims
1. Fungizide Mischung, enthaltend1. Fungicidal mixture containing
a) eine fungizid wirksame Verbindung der Formel IA bzw. IBa) a fungicidally active compound of the formula IA or IB
Figure imgf000030_0001
in denen ^-^ für eine Einfach- oder Doppelbindung steht und der Index und die Substituenten die folgende Bedeutung haben:
Figure imgf000030_0001
in which ^ - ^ stands for a single or double bond and the index and the substituents have the following meaning:
R' -C [C0CH3] =CHOCH3 , -C [C02CH3] =N0CH3 , -C [CONHCH3] =NOCH3 , -C [C02CH3] =CHCH3 , -C [C02CH3] =CHCH2CH3 , -C [COCH3] =NOCH3 , -C [COCH2CH3]=NOCH3, -N (OCH3) -C02CH3 ,R '-C [COCH 3 ] = CHOCH 3 , -C [CO 2 CH 3 ] = NOCH 3 , -C [CONHCH 3 ] = NOCH 3 , -C [CO 2 CH 3 ] = CHCH 3 , -C [CO 2 CH 3 ] = CHCH 2 CH 3 , -C [COCH 3 ] = NOCH 3 , -C [COCH 2 CH 3 ] = NOCH 3 , -N (OCH 3 ) -C0 2 CH 3 ,
-N (CH3 ) -C02CH3 , -N (CH2CH3 ) -C02CH3 ;-N (CH 3 ) -C0 2 CH 3 , -N (CH 2 CH 3 ) -C0 2 CH 3 ;
R" ein C-organischer Rest, welcher direkt oder über eine Oxy-, Mercapto-, Amino-, oder Alkylaminogruppe gebunden ist;R "is a C-organic radical which is bonded directly or via an oxy, mercapto, amino or alkylamino group;
zusammen mit einer Gruppe X und dem Ring Q bzw. T, an den sie gebunden sind, ein ggf. subst. bicycli- sches, partiell oder vollständig ungesättigtes Sy- stem, welches neben Kohlenstoffringgliedern Heteroatome aus der Gruppe Sauerstoff, Schwefel und Stickstoff enthalten kann;together with a group X and the ring Q or T to which they are attached, a subst. bicyclic, partially or completely unsaturated system which, in addition to carbon ring members, can contain heteroatoms from the group consisting of oxygen, sulfur and nitrogen;
Rx -OC [C02CH3] =CH0CH3 , -OC [C02CH3] =CHCH3 , -OC[C02CH3]=CHCH2CH3, -SC [C02CH3] =CH0CH3 ,R x -OC [C0 2 CH 3 ] = CH0CH 3 , -OC [C0 2 CH 3 ] = CHCH 3 , -OC [C0 2 CH 3 ] = CHCH 2 CH 3 , -SC [C0 2 CH 3 ] = CH0CH 3 ,
-SC [C02CH3] =CHCH3 , -SC [C0 CH3] =CHCH2CH3 , -N(CH3)C [C0 CH3] =CHOCH3, -N(CH3)C [C02CH3] =NOCH3 , -CH2C [CO2CH3] =CHOCH3, -CH2C [C02CH3] =NOCH3 , -CH2C [CONHCH3] =NOCH3 ;-SC [C0 2 CH 3 ] = CHCH 3 , -SC [C0 CH 3 ] = CHCH 2 CH 3 , -N (CH 3 ) C [C0 CH 3 ] = CHOCH 3 , -N (CH 3 ) C [C0 2 CH 3] = NOCH 3, -CH 2 C [CO 2 CH 3] = CHOCH 3, -CH 2 C [C0 2 CH 3] = NOCH 3, -CH 2 C [CONHCH 3] = NOCH 3;
Ry Sauerstoff, Schwefel, =CH- oder =N-;R y oxygen, sulfur, = CH- or = N-;
n 0, 1, 2 oder 3, wobei die Reste X verschieden sein können, wenn n größer als 1 ist; X Cyano, Nitro, Halogen, Cι-C4-Alkyl, Cι-C4-Halogen- alkyl, Cι~C4-Alkoxy, Cι-C4-Halogenalkoxy, Cχ-C4-Alkylthio;n is 0, 1, 2 or 3, where the radicals X can be different if n is greater than 1; X is cyano, nitro, halogen, Cι-C 4 -alkyl, halo-C 4 alkyl, Cι ~ C 4 -alkoxy, C 4 haloalkoxy, Cχ-C4-alkylthio;
für den Fall, daß n > 1 ist, eine an zwei benachbarte C-Atome des Phenylrings gebundene C3-C5-Alkylen-, C3-C5-Alkenylen- , Oxy-C -C4-alkylen-, Oxy-Cχ-C -alkylenoxy- , Oxy-C2-C4-alkenylen- , Oxy-C2-C4-alkenylenoxy- oder Butadiendiylgruppe, wo- bei diese Ketten ihrerseits ein bis drei der folgenden Reste tragen können: Halogen, Cι.-C4-Alkyl , Cι-C4-Halogenalkyl, Cι-C4-Alkoxy, Cι-C4-Halogenalkoxy oder Cι-C -Alkylthio,in the event that n> 1, a C 3 -C 5 alkylene, C 3 -C 5 alkenylene, oxy-C -C 4 alkylene, oxy- bonded to two adjacent C atoms of the phenyl ring Cχ-C -alkyleneoxy, oxy-C 2 -C 4 -alkenylene, oxy-C 2 -C 4 -alkenyleneoxy or butadienediyl group, where these chains can in turn carry one to three of the following radicals: halogen, Cι . -C 4 -alkyl, -C-C 4 -haloalkyl, -C-C 4 -alkoxy, Cι-C 4 -haloalkoxy or Cι-C -alkylthio,
Y =C- oder -N- ;Y = C- or -N-;
Q Cyclopentenyl, Cyclohexenyl, Phenyl, Pyrrolyl, Thienyl, Furyl, Pyrazolyl, Imidazolyl, Oxazolyl, Isoxazolyl, Thiazolyl, Thiadiazolyl, Triazolyl, Pyridinyl, 2-Pyridonyl, Pyrimidinyl und Triazinyl;Q cyclopentenyl, cyclohexenyl, phenyl, pyrrolyl, thienyl, furyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, triazolyl, pyridinyl, 2-pyridonyl, pyrimidinyl and triazinyl;
T Phenyl, Oxazolyl, Thiazolyl, Thiadiazolyl, Oxa¬ diazolyl, Pyridinyl, Pyrimidinyl und Triazinyl,T is phenyl, oxazolyl, thiazolyl, thiadiazolyl, diazolyl oxa ¬, pyridinyl, pyrimidinyl and triazinyl,
sowiesuch as
bl) den herbiziden Wirkstoff IIbl) the herbicidal active ingredient II
Figure imgf000031_0001
Figure imgf000031_0001
und/oderand or
b2) den herbiziden Wirkstoff IIIb2) the herbicidal active ingredient III
Figure imgf000031_0002
in einer synergistisch wirksamen Menge.
Figure imgf000031_0002
in a synergistically effective amount.
2. Fungizide Mischung nach Anspruch 1, dadurch gekennzeichnet, daß das Gewichtsverhältnis der Verbindungen IA bzw. IB zu der Verbindung II oder III 10:1 bis 0,1:1 und das Gewichts- Verhältnis der Verbindungen IA bzw. IB zu der Verbindung II und der Verbindung III 10:1:0,4 bis 0,1:1:0,4 beträgt.2. Fungicidal mixture according to claim 1, characterized in that the weight ratio of the compounds IA or IB to the compound II or III 10: 1 to 0.1: 1 and the weight The ratio of the compounds IA or IB to the compound II and the compound III is 10: 1: 0.4 to 0.1: 1: 0.4.
3. Verfahren zur Bekämpfung von Schadpilzen, dadurch gekenn- zeichnet, daß man die Schadpilze, deren Lebensraum oder die von ihnen freizuhaltenden Pflanzen, Samen, Böden, Flächen, Materialien oder Räume mit einer Verbindung der Formel IA oder IB gemäß Anspruch 1 und der Verbindung der Formel II gemäß Anspruch 1 und/oder der Verbindung III gemäß Anspruch 1 behandelt.3. A method for combating harmful fungi, characterized in that the harmful fungi, their habitat or the plants, seeds, soils, areas, materials or spaces to be kept free by them with a compound of formula IA or IB according to claim 1 and the compound of the formula II according to claim 1 and / or of the compound III according to claim 1.
4. Verfahren nach Anspruch 3, dadurch gekennzeichnet, daß man die Verbindung IA oder IB gemäß Anspruch 1 und die Verbindung II gemäß Anspruch 1 und/oder die Verbindung III ge- maß Anspruch 1 gleichzeitig, und zwar gemeinsam oder ge¬ trennt, oder nacheinander ausbringt.4. The method according to claim 3, characterized in that the compound IA or IB according to claim 1 and the compound II according to claim 1 and / or the compound III according to claim 1 simultaneously, namely together or ge ¬ separated, or in succession deploys.
5. Verfahren zum Schutz von Kulturpflanzen vor Schadpilzen gemäß Anspruch 3, dadurch gekennzeichnet, daß man die Schad- pilze, ihren Lebensraum oder die von ihnen freizuhaltenden Pflanzen, Samen oder Böden mit 0,01 bis 1 kg/ha einer Verbindung IA oder IB gemäß Anspruch 1 behandelt.5. A method of protecting crop plants from harmful fungi according to claim 3, characterized in that the harmful fungi, their habitat or the plants, seeds or soil to be kept free of them with 0.01 to 1 kg / ha of a compound IA or IB according to Claim 1 treated.
6. Verfahren nach Anspruch 5, dadurch gekennzeichnet, daß man die Verbindung II gemäß Anspruch 1 in einer Menge von 0,01 bis 1 kg/ha anwendet.6. The method according to claim 5, characterized in that the compound II according to claim 1 is used in an amount of 0.01 to 1 kg / ha.
7. Verfahren nach Anspruch 5, dadurch gekennzeichnet, daß man die Verbindung III gemäß Anspruch 1 in einer Menge von 0,001 bis 0,3 kg/ha anwendet.7. The method according to claim 5, characterized in that the compound III according to claim 1 is used in an amount of 0.001 to 0.3 kg / ha.
8. Verfahren zum Schutz von Materialien oder Räumen vor Schadpilzen gemäß Anspruch 3, dadurch gekennzeichnet, daß man die von Schadpilzen freizuhaltenden Materialien oder Räume mit 0,01 bis 20 g/m3 einer Verbindung IA oder IB gemäß Anspruch 1 behandelt.8. A method for protecting materials or rooms from harmful fungi according to claim 3, characterized in that the materials or rooms to be kept free of harmful fungi are treated with 0.01 to 20 g / m 3 of a compound IA or IB according to claim 1.
9. Verfahren nach Anspruch 8, dadurch gekennzeichnet, daß man die Verbindung II gemäß Anspruch 1 in einer Menge von 0,01 bis 20 g/m3 anwendet.9. The method according to claim 8, characterized in that the compound II according to claim 1 is used in an amount of 0.01 to 20 g / m 3 .
10. Verfahren nach Anspruch 8, dadurch gekennzeichnet, daß man die Verbindung III gemäß Anspruch 1 in einer Menge von 0,01 bis 20 g/m3 anwendet. 10. The method according to claim 8, characterized in that the compound III according to claim 1 is used in an amount of 0.01 to 20 g / m 3 .
11. Verwendung einer Verbindung IA bzw. IB gemäß Anspruch 1 zur Herstellung einer fungizid wirksamen synergistischen Mischung gemäß Anspruch 1.11. Use of a compound IA or IB according to claim 1 for the preparation of a fungicidally active synergistic mixture according to claim 1.
12. Verwendung der Verbindung II gemäß Anspruch 1 zur Herstellung einer fungizid wirksamen synergistischen Mischung gemäß Anspruch 1.12. Use of the compound II according to claim 1 for the preparation of a fungicidally active synergistic mixture according to claim 1.
13. Verwendung der Verbindung III gemäß Anspruch 1 zur Herstel - lung einer fungizid wirksamen synergistischen Mischung gemäß Anspruch 1. 13. Use of the compound III according to claim 1 for the production of a fungicidally active synergistic mixture according to claim 1.
PCT/EP1998/001034 1997-03-14 1998-02-23 Fungicide mixture WO1998041094A1 (en)

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PCT/EP1998/001034 WO1998041094A1 (en) 1997-03-14 1998-02-23 Fungicide mixture

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WO2000030450A1 (en) * 1998-11-19 2000-06-02 Basf Aktiengesellschaft Fungicidal mixtures
WO2000036921A1 (en) * 1998-12-22 2000-06-29 Basf Aktiengesellschaft Fungicide mixture
WO2006120231A2 (en) * 2005-05-12 2006-11-16 Basf Aktiengesellschaft Method of enhancing resistibility of crop plants
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CA2565419A1 (en) * 2004-05-13 2005-11-24 Basf Aktiengesellschaft Fungicide mixtures based on a triazolopyrimidine derivative

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Cited By (18)

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US6503936B1 (en) 1998-11-19 2003-01-07 Basf Aktiengesellschaft Fungicidal mixtures
WO2000030450A1 (en) * 1998-11-19 2000-06-02 Basf Aktiengesellschaft Fungicidal mixtures
AU767577B2 (en) * 1998-11-19 2003-11-20 Basf Aktiengesellschaft Fungicidal mixtures
CN1293809C (en) * 1998-12-22 2007-01-10 巴斯福股份公司 Fungicide mixture
CZ301438B6 (en) * 1998-12-22 2010-03-03 Basf Aktiengesellschaft Fungicidal mixtures and use thereof
JP2002532524A (en) * 1998-12-22 2002-10-02 ビーエーエスエフ アクチェンゲゼルシャフト Fungicide mixture
AU769532B2 (en) * 1998-12-22 2004-01-29 Basf Aktiengesellschaft Fungicide mixture
US6541500B1 (en) 1998-12-22 2003-04-01 Basf Aktiengesellschaft Fungicide mixture
WO2000036921A1 (en) * 1998-12-22 2000-06-29 Basf Aktiengesellschaft Fungicide mixture
WO2006120231A2 (en) * 2005-05-12 2006-11-16 Basf Aktiengesellschaft Method of enhancing resistibility of crop plants
WO2006120231A3 (en) * 2005-05-12 2007-08-23 Basf Ag Method of enhancing resistibility of crop plants
WO2010149732A2 (en) 2009-06-25 2010-12-29 Basf Se Use of agrochemical mixtures for increasing the health of a plant
WO2010149732A3 (en) * 2009-06-25 2011-06-30 Basf Se Use of agrochemical mixtures for increasing the health of a plant
CN102458111A (en) * 2009-06-25 2012-05-16 巴斯夫欧洲公司 Use of agrochemical mixtures for increasing the health of plant
CN102458111B (en) * 2009-06-25 2014-07-30 巴斯夫欧洲公司 Use of agrochemical mixtures for increasing the health of plant
EA023113B1 (en) * 2009-06-25 2016-04-29 Басф Се Use of agrochemical mixtures for increasing the health of a plant
EA027489B1 (en) * 2009-06-25 2017-07-31 Басф Се Use of agrochemical mixtures for increasing the health of a plant
EP3213635A1 (en) 2009-06-25 2017-09-06 Basf Se Use of agrochemical mixtures for increasing the health of a plant

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AR012558A1 (en) 2000-11-08
CO5060422A1 (en) 2001-07-30
DE19710760A1 (en) 1998-09-17
AU6724098A (en) 1998-10-12

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