NZ289867A - Fungicidal preparation and method using active compounds inhibiting respiration at the cytochrome complex iii - Google Patents

Fungicidal preparation and method using active compounds inhibiting respiration at the cytochrome complex iii

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Publication number
NZ289867A
NZ289867A NZ289867A NZ28986795A NZ289867A NZ 289867 A NZ289867 A NZ 289867A NZ 289867 A NZ289867 A NZ 289867A NZ 28986795 A NZ28986795 A NZ 28986795A NZ 289867 A NZ289867 A NZ 289867A
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New Zealand
Prior art keywords
c02ch3
formula
alkyl
iia
unsubstituted
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NZ289867A
Inventor
Harald Kohle
Eberhard Ammermann
Gisela Lorenz
Franz Rohl
Herbert Bayer
Hubert Sauter
Karl Eicken
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Basf Ag
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Publication of NZ289867A publication Critical patent/NZ289867A/en

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    • 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
    • A01N47/20—N-Aryl derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N61/00—Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action

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  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Compounds Of Unknown Constitution (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pretreatment Of Seeds And Plants (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Threshing Machine Elements (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Electrical Discharge Machining, Electrochemical Machining, And Combined Machining (AREA)

Abstract

The invention concerns a method of combating harmful fungi which is characterized in that the fungi, their biosphere or the materials, plants, seeds, soils, surfaces or areas to be protected from fungal infection are treated simultaneously together or separately or successively with an active substance I which inhibits the respiration of cytochrome complex III and a) with an active substance of formula IIA, R<1>-CO-NR<2>-OR<3>, in which the substituents have the following meanings: R<1> is hydrogen, alkyl, alkenyl or alkynyl, cycloalkyl or cycloalkenyl, optionally substituted aryl, hetaryl, heterocyclyl, arylcarbonyl or hetarylcarbonyl, R<2>, R<3> designate hydrogen, alkyl or aryl, or b) with an active substance of formula IIB, R<a>-CO-NR<b>-R<c>, in which the substituents have the following meanings: R<a> is optionally substituted phenyl, furyl, dihydropyranyl, oxathi-inyl, oxathi-inyl dioxide, pyridyl or thiazolyl; R<b> is hydrogen, alkyl or alkoxy; R<c> is optionally substituted phenyl or cyclohexyl, and mixtures suitable therefor.

Description

New Zealand Paient Spedficaiion for Paient Number £89867 New Zealand No. 289867 International No. PCT/EP95/02744 TO BE ENTERED AFTER ACCEPTANCE AND PUBLICATION Priority dates: 21.07.1994; Complete Specification Filed: 13.07.1995 Classification:^) A01N43/50,54,647,76; A01N37/28 Publication date: 28 July 1998 Journal No.: 1430 Title of Invention: Method of combating harmful fungi Name, address and nationality of applicant(s) as in international application form: BASF AKTIENGESELLSCHAFT, a German company of D-67056 Ludwigshafen, Federal Republic of Germany NEW ZEALAND PATENTS ACT 1953 COMPLETE SPECIFICATION 0050/45055 289867 Controlling harmful fungi The present invention relates to a method for controlling harmful 5 fungi and to suitable synergistic mixtures for this purpose which, in addition to an acti" a ingredient I which inhibits the respiration at the cytochrome complex III, contains [sic] a) an active ingredient of the formula IIA R1—CO-NR2-OR3 IIA where R1 is hydrogen, Ci-Cio-alkyl, C2-Cio-alkenyl or C3-Cio-alkynyl, C3~C8-cycloalkyl or C^Ca-cycloalkenyl, aryl, hetaryl, heterocyclyl, arylcarbonyl or hetaryl-carbonyl, where the radicals may be partially or completely halogenated.and/or may carry from one to 20 three of the following groups: cyano, nitro, hydroxy1, mercapto, amino, carboxyl, aminocarbonyl, anunothiocarbonyl, Ci-C5-alkyl, Ci-C6-haloalkyl, Ci-Cg-alkyl-sulfonyl, Ci-Cg-alkylsulfoxyl, Ci-C6~alkoxy, 25 Ci-C6~haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylthio, Ci-Cg-alkylamino, di-Ci-Cg-alkylamino, Ci-Ce-alkylaminocarbonyl, di-Ci~C6-alkylaminocarbonyl, Ci-Cg-alkylaminothiocarbonyl, di-Ci-C6~alkylaminothiocarbonyl, 30 - C2-C6~alkenyl, C2-C6~alkenyloxy or Ci-Cg-alkyl- carbonyl, where these groups may be partially or completely halogenated, C3-C6-cycloalkyl, benzyl, benzyloxy, aryl, aryl-oxy, arylthio, hetaryl, hetaryloxy or 35 hetaarylthio [sic], where these groups may be partially or completely halogenated and/or may carry from one to three of the following radicals: cyano, nitro, hydroxyl, Ci~C4-alkyl, Ci-C4~haloalkyl, Ci~C4-alkoxy, Ci~C4-haloalkoxy 40 or Ci-C4~alkylthio, C (=N0Ri) -Ax-Rii, where R^R11 independently of one another are each hydrogen or Ci-C6~alkyl, A is oxygen, sulfur or NH and 45 x is 0 or 1, and C 0050/45055 28986 R2 and R3 independently of one another are each hydrogen, Ci-C6-alkyl or aryl or contain b) an active ingredient of the formula IIB Ra-C0-Rb-Rc IIB where Ra is phenyl, furyl, dihydropyranyl, oxathiinyl, oxathi-inyl dioxide, pyridyl or thiazolyl, where these radicals may carry from one to three of the following substituents: halogen, Ci-C4~alkyl, C1-C4- haloalkyl, 15 Ci~C4-alkoxy, Ci-C4~haloalkoxy or C1-C4- alkylthio; Rb is hydrogen, Ci~C4-alkyl or Ci-C4~alkoxy and Rc is phenyl or cyclohexyl, where these rings may be 20 partially or completely halogenated and/or may carry from one to three of the following radicals: Ci-C4-alkyl, Ci~C4-haloalkyl, Ci~C4-alkoxy, C1-C4-haloalkoxy or Ci-C4-alkylthio.
It is known from the literature that active ingredients which inhibit the cytochrome bci complex (cytochrome complex III) can be used as fungicides (cf. U. Brandt, U. Haase, H. Schagger and G. von Jagow: "Spezifitat und Wirkmechanismus der Strobilurine", Dechema Monograph Vol. 129, 27-38, VCH Verlagsgesellschaft 30 weinheim, 1993; J.M. Clough: Natural Product Reports, 1993, 565-574; F. Rohl and H. Sauter: Biochem. Soc. Trans. 22, 635 (1993)].
Examples of such active ingredients are compounds of the formula 35 IA or IB ^ R' \r" IA IB 45 where I 289867 R' is -C[C02CH3]=CH0CH3, -C[C02CH3]=NOCH3, -C[CONHCH3]=NOCH3, -C[C02CH3]=CHCH3, -C[C02CH3]=CHCH2CH3, -C[COCH3]=NOCH3, 5 -C[COCH2CH3}=NOCH3, -N(0CH3)-C02CH3, -N(CH3)-C02CH3 or —N(CH2CH3)—C02CH3 , R" is a C-organic radical which is bonded directly or via an oxy, mercapto, amino or alkylamino group, or together with a group X and the ring Q or T to which they are bonded, an unsubstituted or substituted bicyclic, partially or completely unsaturated system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogon, 0050/45055 3 is a double or single bond, Rx is -0C[C02CH3]=CH0CH3, -0C[C02CH3]=CHCH3r -0C[C02CH3]=CHCH2CH3, -SC[C02CH3]=CH0CH3, -SC[C02CH3]=CHCH3, -SC[C02CH3]=CHCH2CH3, -N(CH3)C[C02CH3]=CH0CH3, -N (CH3 )C[C02CH3]=N0CH3, -CH2C[C02CH3]=CH0CH3, -CH2C[C02CH3]=N0CH3 or -CH2C[C0NHCH3]=N0CH3, Ry is oxygen, sulfur, =CH- oder ^N-, n is 0, 1, 2 or 3, and the radicals X may be different when n is > 1, X is cyano, nitro, halogen, Ci-C4~alkyl, Ci-C4~haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Cj-Cij-alkylthio or, where n is > 1, a C3-C5~alkylene, C3-C5~alkenylene, oxy-C2-C4~ alkylene, oxy-Ci-C3-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4~alkenyleneoxy or butadienediyl group bonded to two adjacent carbon atoms of the phenyl ring, where these chains in turn may carry from one to three of the following radicals: halogen, Ci-C4~alkyl, Cx-C4-haloalkyl, Ci-C4~alkoxy, Ci-C4~haloalkoxy or Ci-C4~alkylthio, Y is =C- or -N-, 40 Q is phenyl, pyrrolyl, thienyl, furyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, triazolyl, pyridinyl, 2-pyridonyl, pyrimidinyl or triazinyl and T is phenyl, oxazolyl, thiazolyl, thiadiazolyl, oxadiazolyl, 45 pyridinyl, pyrimidinyl or triazinyl.
A 0050/45055 28986 4 Such active ingredients I (or IA and IB) are described, for example, in the following publications: 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, EJ?- -A 480 795, EP- -A 483 851, EP- -A 483 985, EP- -A 487 409, F-?• -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, 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, 35 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, 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, 40 JP-A 06/025,142, JP-A 06/056,756, FR-A 2 670 781, GB-A 2 210 041, GB-A 2 218 702, GB-A 2 238 308, GB-A 2 249 092, GB-A 2 253 624, GB-A 2 255 092, DE-A 3 9 05 911, German Patent Application 43 05 502.8, German Patent Application 43 10 143.7, German Patent Application 45 43 18 397.2, German Patent Application 43 34 709.6, German patent Application 44 03 446.6, < 0050/45055 289867 German Patent Application 44 03 447.4, German Patent Application 44 03 448.2, German Patent Application 44 10 424.3, German Patent Application 44 21 180.5, German Patent Application 44 21 182.1, German Patent 5 Application 44 15 483.6, German Patent Application 44 23 615.8 and German Patent Application 44 23 612.3.
When these active ingredients are used, however, it is found that their action is only temporary, ie. further growth of the fungus 10 occurs after some time.
Furthermore, the literature discloses compounds IIA [G.R. Schon-baum et al.: Plant Physiol. 42, (1971) 124-128] which inhibit the cyanide-resistant respiration in plants. However, a fungicidal 15 action of such compounds is not known.
Compounds of the formula IIB are disclosed in the literature as fungicides [cf. Modern Selective Fungicides, Edit.: H. Lyr, VEB Gustav Fischer Verlag, Jena, Leipzig, 1987, and the literature 20 cited there]. However, these compounds do not have a broad and satisfactory action spectrum.
It is an object of the present invention to remedy the disadvantages in the use of the compounds IA or IB.
We have found that this object is achieved and that harmful fungi can in principle be better controlled if, in addition to an active ingredient IA or IB which inhibits the respiration at the cytochrome complex III, a further active ingredient of the formu-30 la IIA or of the formula IIB is used.
The novel method is probably based on the fact that, when the respiration at the cytochrome complex III is inhibited, the fungus uses a secondary route of alternative respiration, so that 35 complete destruction does not occur. This would mean that the active ingredients of the formula IIA or IIB are suitable for inhibiting alternative respiration. The combination of inhibition of both the respiration via the cytochrome complex III and that of the alternative respiration might be responsible for ensuring 40 that the fungus is completely destroyed.
By the novel combination of corresponding active ingredients, more effective control of the harmful fungus is achieved since lower application rates of the individual active ingredients are 45 required as a result of the combination of the active ingredients IA or IB and IIA or IIB (synergistic effect). 0050/45055 28986 In the novel method, in principle all active ingredients described in the publications stated at the outset are suitable for inhibiting respiration at the cytochrome complex III, the compounds stated in the examples given there being particularly 5 suitable. Of particular importance are compounds IA and IB where R" is one of the following groups: unsubstituted or substituted aryloxy, unsubstituted or substituted hetaryloxy, unsubstituted or substituted aryloxymethylene, unsubstituted or substituted hetaryloxymethylene, unsubstituted 10 or substituted arylethenylene, unsubstituted or substituted hetarylethenylene or a group RaR(Jc=NOCH2— or RyON=CRSCRe=NOCH2, where Ra, R(3, R^, R6 and Re in general and in particular have the meanings described in the 15 publications which follow: 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, 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, JP-A 05/201,946, 20 JP-A 05/255,012, JP-A 05/294,948, JP-A 06/025,133, JP-A 06/025,142, German Patent Application 44 03 447.., German Patent Application 44 03 448.., German Patent Application 44 21 180.5 and German Patent Application 44 21 182.1.; particularly preferred ansubstituted or substituted aryloxy and unsubstituted or substituted hetaryloxy radicals in general and in particular have the meanings described in the publicaticns which follow: 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, 30 EP-A 280 185, EP-A 307 103, EP-A 341 845, EP-A 382 375, EP-A 393 861, EP-A 198 692, 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, EF-A 515 901, WO-A 93/15,046, . WO-A 94/10,159, GB-A 2 253 624, JP-A 04/182,461 and German Patent 35 Application 44 23 612.3; particularly preferred unsubstituted or substituted aryloxymethylene and unsubstituted or substituted hetaryloxymethylene radicals in general and in particular have the meanings stated in the 40 publications which follow: 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 363 818, 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, 45 EP-A 477 631, EP-A 498 188, EP-A 498 396, EP-A 513 580, EP-A 515 901, EP-A 579 124, WO-A 93/08,180, WO-A 93/15,046, WO-A 94/00,436, JP-A 04/182,461, German Application No. 0050/45055 - - 289867 7 43 05 502.., German Application No. 44 10 424.. and German Patent Application 44 15 483.6; particularly preferred unsubstituted or substituted aryletheny-5 lene and unsubstituted or substituted hetarylethenylene radicals in general and in particular have the meanings described in the publications which follow: 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, WO-A 93/15,046, WO-A 94/11,334, FR-A 2 670 781 and German Patent Application 44 23 615.8; particularly preferred active ingredients of the formula IA where R' is -C [CO2CH3 ] =CH0CH3 correspond in general and in particular to the compounds described in the publications which : follow: 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 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 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, WO-A 90/07,493, WO- -A 92/18, 487, WO-A 92/18, WO-A 93/08,180, WO-A 93/16,986, WO-A 94/00,436, WO-A 94/08,948, WO-A 94/08,968, WO-.. 94/10,159, WO-A 94/11,334, FR-A 2 670 781, 30 JP-A 06/025,133, German Application No. 44 03 447.., German Application No. 44 10 424.. and German Patent Application 44 21 180.5; particularly preferred active ingredients of the formula I where 35 R' is -C[CO2CH3] =NOCH3 correspond in general and in particular to the compounds described in the publications which follow: 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, 40 EP-A 472 300, EP-A 515 901, WO-A 94/00,436, WO-A 94/08,948, WO-A 94/10,159, WO-A 94/11,334, JP-A 05/201,946, JP-A 05/255,012, JP-A 05/294,948, German Application No. 44 03 447.., German Application No. 44 10 424.. and German Patent Application 44 21 180.5; n 0050/45055 28986 8 particularly preferred active ingredients of the formula I where R' is -C[CONBCH3]=N0CH3 correspond in general and in particular to the compounds described in the publications which follow: EP-A 398 692, EP-A 463 488, EP-A 477 631, EP-A 515 901, EP-A 579 124, EP-A 585 751, 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, GB-A 2 253 624, JP-A 04/182,461, JP-A 05/201,946, JP-A 05/255,012, JP-A 05/294,94 8, German Application No. 43 05 502.., German Application No. 44 03 448.., German Application No. 44 10 424.., 10 German Patent Application No. 44 23 615.8 and German Patent Application 44 21 182.1; particularly preferred active ingredients of the formula I where R' is -C [C02CH3 ]=CHCH3 or -C [CO2CH3 ]=CHCH2CH3 correspond in general 15 and in particular to the compounds described in the publications which follow: EP-A 280 185, EP-A 463 488, EP-A 501 901, EP-A 513 580, EP-A 515 901, German Application No. 44 03 447.., German Application No. 44 10 424.., German Patent Application No. 44 21 180.5 and German Patent 20 Application No. 44 15 483.6; particularly preferred active ingredients of the formula I where R' is -C [C0CH3 ]=N0CH3 or -C[C0CH2CH3]=N0CH3 correspond in general and in particular to the compounds described in EP-A 498 188; particularly preferred active ingredients of the formula I where R' is -N(0CH3)-C02CH3, -N(CH3)-C02CH3 or -N(CH2CH3)-C02CH3 correspond in general and in particular to the compounds described in the publications which follow: EP-A 498 396, 30 WO-A 93/15,046, JP-A 06/025,142 and German Patent Application 44 23 612.3; particularly preferred active ingredients of the formula I where R' is -0C[C02CH3]=CH0CH3, -0C[C02CH:]=CHCH3, -0C[C02CH3]=CHCH2CH3, 35 -0C[C0CH2CH3]=N0CH3, -SC[C02CH3]=CH0CH3, -SC[C02CH3]=CHCH3, -SC[C02CH3]=CHCH2CH3, -N(CH3)C[CO2CH3]=CHOCH3, -N(CH3)C[C02CH3]=N0CH3, -CH2C[C02CH3]=CH0CH3, -CH2C[C02CH3]=N0CH3 or -CH2C[CONHCH3]=N0CH3 correspond in general and in particular to the compounds described in the publications which follow: 40 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 and EP-A 584 625. 45 Examples of particularly suitable active ingredients I are listed in the tables below. ♦ 0050/45055 Table 1.1A 28986] Compounds of the formula IA where Q is phenyl, R' is -C (CO2CH3) =CH0CH3, n is 0 and R" is unsubstituted or substituted 5 (het)aryloxymethylene, the unsubstituted or substituted (het)aryl group having the following meanings No. unsubstituted or ftubstituted (het)aryl Reference I.lA-1 2-CH3-C6H4 EP-A 226 917 I.lA-2 2,5-(CH3)2-C6H3 EP-A 226 917 I.lA-3 2-CH3, 4-C[CH3]=NOCH3-C5H3 EP-A 386 561 I.lA-4 2-CH2CH2CH3, 6-CF3-pyrimidin-4-yl EP-A 407 873 I.1A-5 2,4-(CH3)2-C6H3 EP-A 226 917 Table 1.IB Compounds of the formula IA where R' is -C(CO2CH3)=CH0CH3, Q is phenyl, n is 0 and R" is unsubstituttd or substituted (het)aryloxy, the unsubstituted or substituted (het)aryl group having the following meanings No. unsubstituted or substituted (het)aryl Reference I.IB—1 c6h5 EP-A 178 826 i.lB-2 6-[ 2-cn-c6h4-o] -pyrimidin-4-yl EP-A 382 375 Table 1.1C Compounds of the formula IA where R' is -C(C02CH3)=CH0CH3, Q is phenyl, n is 0 and R" is unsubstituted or substituted (het)aryl-35 ethenylene, the unsubstituted or substituted (het)aryl group having the following meanings No. unsubtituted or substituted (het)aryl Reference I.lC-1 l-(2,4-Cl2-C6H3), 5-CF3-pyrazol-4-yl EP-A 528 246 I.lC-2 1- (4-CI-C6H4) -pyrazol-4-yl EP-A 378 755 I.lC-3 3-CF3-C6H4 EP-A 203 606 I.lC-4 3-Cl-C6H4 EP-A 203 606 I.1C-5 4-C6H5-C6H4 EP-A 203 606 40 45 0050/45055 289867 Table 1.1D Compounds of the formula IA where Q is phenyl, R' is -C(C02CH3)=CH0CH3r n is 0 and R" is CH20N=CRaRp, Ra and Rp having 5 the following meanings No.
R° RP Reference I.ID—1 ch3 4-Cl-C6H4 EP-A 370 629 I.ID—2 ch3 3-CF3-C6H4 EP-A 370 629 I.1D-3 ch3 4-OCH2CH3-pyrimidin-2-yl WO-A 92/18,487 Table 1.IE Compounds of the formula IA where Q is phenyl,, R' is -C(C02CH3)=CH0CH3, n is 0 and R" is CH2ON=CRYCK6=NORe, R?, R6 and RE having the following meanings No. rV r° re Reference I.IE—1 ch3 ch3 ch3 German Application 44 03 447.4 1.1E-2 ch3 ch3 CH2CH3 German Application 44 03 447.4 I.lE-3 ch3 c6h5 ch3 German Application 44 03 447.4 I.1E-4 ch3 c6h5 ch2ch3 German Application 44 03 447.4 I..IB-5 ch3 4-Cl-C6H4 ch3 German Application 44 21 180.5 I.lE-6 ch3 4-c1-C5H4 CH2CH3 German Application 44 21 180.5 Table 1.2A Compounds of the formula IA where Q is phenyl, R' is -C(C02CH3)=N0CH3/ n is 0 and R" is unsubstituted or substituted (het)aryloxymethylene, the unsubstituted or substituted (het)aryl 40 group having the following meanings No. unsubstituted or substituted (het)aryl Reference I.2A-1 2-ch3-c6h4 ep-a 253 213 I.2A-2 2,5-(ch3)2-c6H3 ep-a 400 417 0050/45055 28986 11 No. unsubstituted or substituted (het)aryl Reference I.2A-3 2,4-(CH3)2-C6H3 EP-A 400 417 I.2A-4 2/3,5-(CH3)3-C6H2 EP-A 400 417 I.2A-5 2-C1, 5-CH3-C6H3 EP-A 400 417 I.2A-6 2-ch3, 4—C[CH3]=NOCH3-C6h3 EP-A 386 561 Table 1.2B Compounds of the formula IA where Q is phenyl, R' is —C (CO2CH3)=N0CH3, n is 0 and R" is unsubstituted or substituted (het)aryloxy, the unsubstituted or substituted (het)aryl group having the following meanings No. unsubstituted or substituted (het)aryl Reference I.2B-1 c6h5 EP-A 253 213 I.2B-? 6-[ 2-CN-C6H4-0]-pyrimidin-4-yl EP-A 468 684 Table 1.2C Compounds of the formula IA where Q is phenyl, R' is -C(C02CH3)=N0CH3, n is 0 and R" is CH20N=CRaR^, Ra and R^ having the following meanings No.
Ra rP Reference I.2C-1 ch3 4-Cl-C6H4 ep-a 463 488 I.2C-2 ch3 3-Cl-C6H4 ep-a 463 488 I.2C-3 ch3 4-cf3-c6h4 ep-a 463 488 X.2C-4 ch3 3-CF3-C6H4 ep-a 363 488 X.2C-5 ch3 4-CH3-C6H4 ep-a 463 488 I.2C-6 ch3 4-OCH2CH3-pyrimidin-2-yl ep-a 472 300 I.2C-7 ch3 3,5-Cl2-C6H3 ep-a 463 488 Table 1.2D Compounds of the formula IA where -C(C02CH3)=N0CH3( n is 0 and R" is 45 having the following meanings Q is phenyl, R' is CH2ON=CRYCR6=NORE, Ry, R6 and Re 0050/45055 28986 12 No. ry r5 re Reference I.2D-1 ch3 ch3 ch3 German Application 44 03 447.4 I.2D-2 ch3 ch3 ch2ch3 German Application 44 03 447.4 I.2D-3 ch3 c6h5 ch3 German Application 44 03 447.4 I.2D-4 ch3 c6h5 ch2ch3 German Application 44 03 447.4 I.2D-5 ch3 4-Cl-C6H4 ch3 German Application 44 21 180.5 I.2D-6 ch3 4-Cl-C6H4 ch2ch3 German Application 44 21 180.5 Table 1.3A Compounds of the formula IA where Q is phenyl, R' is -C(CONHCH3 )=N0CH3( n is 0 and R" is unsubstituted or substituted 20 (het)aryloxymethylene, the unsubstituted or substituted (het)aryl group having the following meanings No. unsubstituted or substituted (het)aryl Reference I.3A-1 2-CH3-C6H4 EP-A 477 631 I.3A-2 2,5-(CH3)2-C6H3 EP-A 477 631 I.3A-3 2,4—(CH3)2-C6H3 EP-A 477 631 I.3A-4 2,3,5-(CH3)3-C6H2 EP-A 477 631 I.3A-5 2-CH3, 4-C[CH3]=NOCH3-C6H3 EP-A 597 124 I.3A-6 l-[4-Cl-c6h4)-pyrazol—3-yl German Application 43 05 502.8 I.3A-7 l-[2,4-Cl2-C6H3]-pyrazol-3-yl German Application 43 05 502.8 Table 1.3B Compounds of the formula IA where Q is phenyl, R' is -C(CONHCH3)=NOCH3, n is 0 and R" is unsubstituted or substituted (het)aryloxy, the unsubstituted or substituted (het)e.ryl group having the following meanings * 0050/45055 28986; 13 No. unsubstituted or substituted (het)aryl Reference I.3B-1 c6h5 ep-a 398 692 I.3B-2 6-[2-CN-C6H4-0]-pyrimidin-4-yl gb-a 2 253 624 Table 1.3C Compounds of the formula IA where Q is phenyl, R' is -C (CONHCH3) =N0CH3, n is 0 and R" is unsubstituted or substituted (het)arylethenylene, the unsubstituted or substituted (het)aryl group having the following meanings No. unsubstituted or substituted (het)aryl Reference I.3C-1 l-[2,4-Cl2-C6H3], 5-CF3-pyrazol-4-yl German Application 44 23 615.8 Table 1.3D Compounds of the formula IA where Q is phenyl, R' is -C(CONHCH3)=NOCH3, n is 0 and R" is CH2ON=CRaRP, Ra and R^ having the following meanings No.
Ra Reference I.3D—1 ch3 4-Cl-C6H4 EP-A 4 63 488 I.3D-2 ch3 3-Cl-C6H4 EP-A 463 488 I.3D-3 ch3 4—CF3—C6H4 EP-A 585 7V.
I.3D-4 ch3 3-CF3"C6H4 EP-A 585 751 I.3D—5 ch3 4-CH3-C6H4 EP-A 463 488 I.3D-6 ch3 3,5-Cl2-C6h3 EP-A 463 488 I.3D-7 ch3 2-OCH2CH3-pyrimidin~2-yl WO-A 92/13,830 Table 1.3E Compounds of the for™ , a IA where Q is phenyl, R' is -C(CONHCH3)=NOCH3, n is 0 and R" is CH2ON=CRYCR6=NORE, Ry, R6 and RE having the following meanings 45 No.
RY R6 re Reference I.3E-1 ch3 ch3 ch3 German Patent Application 44 21 182.1 0050/450'iii 289867 14 No. ry R5 re Reference I.3E-2 ch3 ch3 CH2CH3 German Patent Application 44 21 182.1 I.3E-3 ch3 c6h5 ch3 German Patent Application 4 4 21 182.1 I.3E-4 ch3 c6h5 CH2CH3 German Patent Application 44 21 182.1 I.3E-5 ch3 4—ci-C5H4 ch3 German Patent Application 44 21 182.1 I.3E-6 ch3 4-Cl-C6H4 CH2CH3 German Patent Application 44 21 182.1 I.3E-7 ch3 4-F-C6H4 ch3 German Patent Application 44 21 182.1 Table 1.4A Compounds of the formula IA where Q is phenyl, R' is -C (CO2CH3)=CHCH31 n is 0 and R" is unsubstituted or substituted 20 (het)aryloxymethylene, the unsubstituted or substituted (het)aryl group having the following meanings No. unsubstituted or substituted (het)aryl Reference H > 1 H 2-CH3-C6H4 EP-A 280 185 I.4A-2 2,5-(CH3)2-C6H3 EP-A 513 580 I.4A-3 2,4-(CH3)2-C6H3 EP-A 513 580 I.4A-4 2,3,5-(CH3)3-C6H2 EP-A 513 580 I.4A—5 2-CI, 5-CH3-C6H3 EP-A 513 580 I.4A-6 2-CH3, 4-C[CH3]=N0CH3-C6H3 EP-A 513 580 H > 1 -J l-[ 4-C1-CsH4 ]-pyrazol-3-yl i_ ■— German Patent Application 44 15 483.6 Table 1.4B Compounds of the formula IA where Q is phenyl, R' is 4Q -C (CO2CH3) =CHCH3, n is 0 and R" is unsubstituted or substituted (het)aryloxy, the unsubstituted or substituted (het)aryl group having the following meanings 45 No. unsubstituted or substituted (het)aryl Reference I.4B-1 c6h5 EP-A 513 580 ? 0050/45055 Table 1.4C 28986; Compounds of the formula IA where Q is phenyl, R' is -C(C02CH3)=CHCH3, n is 0 and R" is CH2ON=CRYCR6=NORE, Ry, R6 and RE 5 having the following meanings Ho. rv r5^ re Reference i.4c-1 ch3 ch3 ch3 German Patent Application 44 21 180.5 i.4c-2 ch3 ch3 ch2ch3 German Patent Application 44 21 180.5 i.4c-3 ch3 c6h5 ch3 German Patent Application 44 21 180.5 i.4c-4 ch3 c6h5 ch2ch3 German Patent Application 44 21 180.5 i.4c-5 ch3 4-Cl-C6H4 ch3 German Patent Application 44 21 180.5 i.4c-6 ch3 4-Cl-C6H4 ch2ch3 German Patent Application 44 21 180.5 Table 1.5A Compounds of the formula IA where Q is phenyl, R' is -C (C02CH3) =CHCH2CH3, n is 0 and R" is unsubstituted or substituted (het)aryloxymethylene, the unsubstituted or substituted (het)aryl group having the following meanings No. unsubstituted or substituted (het)aryl Reference I.5A-1 2-CH3-C6H4 EP-A 513 580 I.5A-2 2,5-(CH3)2-C6H3 EP-A 513 580 I.5A-3 2,4-(CH3)2-C6H3 EP-A 513 580 I.5A-4 2,3,5-(CH3)3-C6H2 EP-A 513 580 I.5A-5 2-CI, 5-CH3-C6H3 EP-A 513 580 I.5A-6 2-CH3, 4-C[CH3]=NOCH3-C6H3 EP-A 513 580 40 Table 1.5B 45 Compounds of the formula IA where Q is phenyl, R' is -C (C02CH3) =CHCH2CH3, n is 0 and R" is unsubstituted or substituted (het)aryloxy, the unsubstituted or substituted (het)aryl group having the following meaning 0050/45055 28986 16 No. unsubstituted or substituted (het)aryl Reference I.5B-1 C6Hs EP-A 513 580 Table 1.5C Compounds of the formula IA where Q is phenyl, R' is -C(C02CH3)=CHCH2CH3, n is 0 and R" is CH2ON=CRYCR6=NORE, RY, R6 and RE having the following meanings No. ry r6 re Reference i.5c-1 ch3 ch3 ch3 German Patent Application 44 21 180.5 i.5c-2 ch3 ch3 ch2ch3 German Patent Application 44 21 180.5 i.5c-3 ch3 c6h5 ch3 German Patent Application 44 21 180.5 i.5c-4 ch3 c6h5 ch2ch3 German Patent Application 44 21 180.5 i.5c-5 ch3 4-Cl-C6H4 ch3 German Patent Application 44 21 180.5 i.5c-6 ch3 4-Cl-C6H4 ch2ch3 German Patent Application 44 21 180.5 Table 1.6A Compounds of the formula IA where Q is phenyl, R' is 30 -C (C0CH3 )=N0CH3, n is 0 and R" unsubstituted or substituted (het)aryloxymethylene^ the unsubstituted or substituted (het)aryl group having the following meanings 40 No. unsubstituted or substituted (het)aryl Reference I.6A-1 2-CH3-C6H4 EP-A 498 188 I.6A-2 2.-5-(CH3)2-C6H3 EP-A 498 188 I.6A-3 2,4-(CH3)2-C6H3 EP-A 498 188 I.6A-4 2,3,5-(CH3)3-C6H2 EP-A 498 188 I.6A-5 2-CH3, 4-C[CH3]=NOCH3-C6H3 EP-A 498 188 45 0050/45055 289867 17 Table 1.6B Compounds of the formula IA where Q is phenyl, R' is -C(C0CH3)=N0CH3, n is 0 and R" is unsubstituted or substituted 5 (het)aryloxy, the unsubstituted or substituted (het)aryl group having the following meanings No. unsubstituted or substituted (het)aryl Reference i.6B-1 c6h5 ep-a 498 188 I.63-2 6-[2-CN-c6h4-0]-pyrimidin-4-yl ep-a 498 188 Table 1.7A Compounds of the formula IA where Q is phenyl, R' is -C (COCH2CH3)=NOCH3, n is 0 and R" is unsubstituted or substituted (het)aryloxymethylene, the unsubstituted or substituted (het)aryl group having the following meanings No. unsubstituted or substituted (het)aryl Reference I.7A-1 2-CH3-C6H4 EP-A 498 188 I.7A-2 2,5-(CH3)2-C6H3 EP-A 498 188 I.7A-3 2,4-(CH3)2-C6H3 EP-A 498 188 I.7A-4 2,3,5-(CH3)3-C6H2 EP-A 498 188 I.7A-5 2-CH3, 4-C[CH3]=NOCH3-C6H3 EP-A 498 188 Table 1.7B Compounds of the formula IA where Q is phenyl, R' is -C(COCH2CH3) =NOCH31 n is 0 and R" is unsubstituted or unsubstituted (het)aryloxy, the unsubstituted or substituted (het)aryl group having the following meanings 40 No. unsubstituted or substituted (het)aryl Reference I.7B-1 c6h5 EP-A 498 188 I.7B-2 6- [ 2-cn-c6h4-0 ] -pyrimidin-4-yl EP-A 498 188 45 0050/45055 289867 18 Table 1.8A Compounds of the formula IA where Q is phenyl, R' is -N(0CH3)-CO2CH3, n is 0 and R" is unsubstituted or substituted 5 (het)aryloxymethylene, the unsubstituted or substituted (het)aryl group having the following meanings NO. unsubstituted or substituted (het)aryl Reference I.8A-1 2-CH3-C5H4 WO-A 93/15,046 I.8A-2 2,5-(CH3)2-C6H3 WO-A 93/15,046 X.8A-3 2,4-(CH3)2-C6H3 WO-A 93/15,046 I.8A-4 2,3(5-(CH3)3-C6H2 WO-A 93/15,046 I.8A-5 2-CI, 5-CH3-C6H3 WO-A 93/15,046 I.8A—6 2-CH3, 4-C[CH3]=NOCH3-C6H3 WO-A 93/15,046 I.8A—7 2-CH3, 4-C[CH3]=NOCH2CH3-C6H3 WO-A 93/15,046 I.8A-8 2-CH3, 4-C[CH2CH3]=NOCH3-C6H3 WO-A 93/15,046 I.8A—9 2-CH?, 4-C[CH2CH3]=NOCH2CH3-C6H3 WO-A 93/15,046 I.8A—10 l-[4-CI-C6H4]-pyrazol-3-yl German Patent Application 44 23 612.3 Table 1.8B Compounds of the formula IA where Q is phenyl, R' is -N (OCH3) —CO2CH3, n is 0 and R" is CH20N=CRaR^, where Ra and R^ have 30 the following meaning No.
Ra RH Reference I.8B-1 CH3 3,5-Cl2-C6H3 WO-A 93/15,046 40 45 0050/45055 ?8 Q 86 19 Examples of particularly suitable active ingredients of the formula IA are listed in the table below No.
R1 R2 R3 Reference IIA. 1 2-OH-C6H5 H H J. Am. Chem. Soc. Ill (1989), 114-120 IIA.2 c6h5 H H Org. Synth. Col. Vol. II, (1943), 67 IIA.3 3,5-Cl2-C6H3 CH3 H Similar to J. Org. Chem. 2A (1959), 802 IIA.4 4-CH3-C6H4 H H J. Indian Chem. Soc. (1974), 437 j IIA.5 2-CI-c5h4 H ch3 Tetrahedron 42 (1987), 5375 IIA.6 2,6-Cl2-C6H3 H H EP-A 133 155 IIA.7 3,5-Cl2-C6H3 H H J. Med. Chem. 11 (1970), 571 IIA.8 2—OH, 3,5-Br2-C6H2 H H Gazz. Chim. Ital. IS. (1948), 536 IIA. 9 3-I-C6H4 H H Bull. Acad. Pol. Sci. Ser. Sci. Chim. 12. (1964), 733 IIA.10 3-Cl-C6H4 H H Bull. Acad. Pol. Sci. Ser. Sci. Chim. 12. (1964), 733 45 0050/45055 289867 Examples of particularly suitable active ingredients of the formula IIB are listed in the table below No.
Ra Rb Rc Reference IIB. 1 2-CHa-l,4-oxa-thiin-3-yl h c6h5 Carboxin US-A 3,249,499 US-A 3,393,202 US-A 3,454,391 IIB.2 2-ch3-I,4-oxa-thiin-3-yl-4,4-dioxide H c6h5 Oxycarboxin US-A 3,399,214 US-A 3,402,241 US-A 3,454,391 IIB.3 2,4,5-(CH3) 3-furan-3—yl H c6h5 Methfluroxam DE-A 20 0» 471 IIB.4 2-ch3-4,5-di- hydro- pyran-3-yl h c6h5 Pyracarbol_d DE-A 16 68 790 IIB.5 2-I-C6H4 H c6h5 Benodanil DE-A 16 42 224 IIB.6 2-CH3-C6H4 H 3-OCH(CH3)2-C6H4 Mepronil GB-A 1 421 112 IIB.7 2-CF3-C6-H4 H 3-OCH(CH3)2-C6H4 Flutolanil JP-A 01/104,514 IIB.8 2-CH3~furan -3-yl H c6h5 Fenfuram GB-A 1 215 066 IIB.9 2-CH3-CbH4 H c6h5 Mebenil DE-A 16 42 224 IIB.10 2,4-(CH3)2-thiazol-5—yl H c6h5 Metsulfovax US-A 3,547,912 US-A 3,505,055 US-A 3,709,992 US-A 3,725,427 IIB.11 2,5-(C.H3)2-furan-3-yl och3 Cyclohexyl Furmecyclox DE-A 24 55 082 IIB.12 2-Cl-pyridin -3-yl H 2,3-[CH(CH3)CH2C(CH3)2 ] -c6h3 EP-A 256 503 IIB.13 2-ch3, 4-cf3-thiazol-5-yl H 2,6-Br2, 4-OCF3-C6H2 EP-A 371 950 40 In providing the mixtures, it is preferable to use the pure active ingredients IA or IB and IIA or IIB, with which, depending on requirements, further active ingredients against pests (for example insects, arachnids or nematodes) or harmful fungi or else 45 herbicidal or growth-regulating active ingredients or fertilizers may be mixed. 0050/45055 289867 21 The mixtures of the compounds IA or l"1 and IIA or IIB and simultaneous joint or separate use of the compounds IA or IB and IIA or IA or IB and IIB are distinguished by an excellent action against a broad spectrum of, in particular, phytopathogenic fun-5 gi. Some of them have systemic activity (ie. when used for plant protection, they can be absorbed by the treated plant without loss of activity and may be transported in the plant) and can therefore also be used as foliage fungicides and soil fungicides.
They are particularly important for controlling a large number of fungi in various crops, such as cotton, vegetable plants (for example cucumbers, beans and cucurbitaceae), barley, grass, oats, coffee, corn, fruit plants, rice, rye, soybean, grapevines, wheat, ornamentals and sugar cane, and a large number of seeds.
They are particularly suitable for controlling the following phytopathogenic fungi: Erysiphe graminis (powdery mildew) on cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbitaceae, Podosphaera leucotricha on apples, Puccinia 20 species on cereals, Rhizoctonia species on cotton and lawns, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinera (gray mold) on strawberries and grapevines, Cercospora arachidicola on peanuts, Pseudocerco-25 sporella herpotrichoides on wheat and barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Plasmopara viticola on grapevines, Alternaria species on vegetables and fruit and Fusarium and Verticillium species.
They can also be used in material protection (for example wood preservation), for example against Paecilomyces variotii.
The compounds IA or IB and IIA or IA or IB and IIB can be applied simultaneously together or separately or in succession, the order 35 in the case of separate application generally having no effect on the success of control.
The compounds IA or IB and IIA are usually used in a weight ratio of from 5:10 to 1:50, preferably from 2:1 to 1:20, in particular 40 from 1:1 to 1:10 (I:IIA).
The compounds IA or IB and IIB are usually used in a weight ratio of from 10:1 to 1:10, preferably from 5:1 to 1:5, in particular from 2:1 to 1:2 (I:IIB). 0050/45055 289867 22 The application rates of the novel mixtures are from 0.015 to 10, preferably from 0.1 to 7, in particular from 0.2 to 3, kg/ha, depending on the type of effect desired.
The application rates of the compounds IA and IB are from 0.005 to 3, preferably from 0.02 to 2, in particular from 0.05 to 1, kg/ha.
The application rates of the compounds IIA are in general from 10 0.05 to 10, preferably from 0.1 to 5, in particular from 0.2 to 2, kg/ha.
The application rates of the compounds IIB are in general from 0.01 to 5, preferably from 0.1 to 2, in particular from 0.2 to 15 1, kg/ha.
In the seed treatment, the application rates of the mixture ar3 in general from 0.001 to 0.1, preferably from 0.002 to 0.05, in particular from 0.005 to 0.5 [sic], g/kg of seed.
If phytopathogenic fungi are to be controlled, the joint or separated application of the compounds IA or IB and IIA or IA or IB and IIB or of the mixtures of the compounds IA or IB and IIA or IA or IB and IIB is effected by spraying or dusting the seeds, 25 the plants or the soils before or after sowing of the plants or before or after germination of the plants.
The novel fungicidal synergistic mixtures or the compounds IA or IB and IIA or IA or IB and IIB can be formulated, for example, in 30 the form of directly sprayable solutions, powders and suspensions or in the form of highly concentrated agueous, oily or other suspensions, dispersions, emulsions, oil dispersions, pastes, dusting agents, broadcasting agents or granules and can be applied by spraying, nebulizing, dusting, broadcasting or pouring. The ap-35 plication form is dependent on the intended use; it should in any case ensure very fine and uniform distribution of the novel mixture .
The formulations are prepared in a manner known per se, for exam-40 pie by adding solvents and/or carriers. Usually, inert additives, such as emulsifiers or dispersants, are mixed with the formulations .
Suitable surfactants are the alkali metal, alkaline earth metal 45 and ammonium salts of aromatic sulfonic acids, for example lig-ninsulfonic, phenolsulfonic, naphthalenesulfonic and dibutylnaph-thalenesulfonic acid, and of fatty acids, alkylsulfonates, i 0050/45055 289867 23 alkyl-arylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols or fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, con-5 densates of naphthalene or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxy-lated isooctyl-, octyl- or nonylphenol, alkylphenol [sic] poly-glycol ether, tributylphenyl polyglycol ether, alkylaryl polyeth-er alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide 10 condensates, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxypropylene, lauryl alkyl polyglycol ether acetal, sorbitol esters, ligninsulfite waste liquors or methylcellulose.
Powders, broadcasting and dusting agents can be prepared by mix-15 ing or milling compounds IA or IB and IIA or IA or IB and IIB or the mixtures of the compounds IA or IB and IIA or IA or IB and IIB together with a solid carrier.
Granules (for example coated, impregnated or homogeneous gran-20 ules) are usually prepared by binding the active ingredient or the active ingredients to a solid carrier.
The fillers or solid carriers used are, for example, mineral earths, such as silica gel, silicas, silicates, talc, kaolin, 25 limestone, lime, chalk, bole, loess, clay, dolomite, kieselguhr, calcium sulfate, magnesium sulfate, magnesium oxide, milled plastics and fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and vegetable products, such as grain flour, bark meal, wood meal and nutshell meal, cellulos-30 ic powders or other solid carriers.
The formulations contain in general from 0.1 to 95, preferably from 0.5 to 90, % by weight of one of the compounds IA or IB, IIA or IIB or of the mixture of the compounds IA or IB and IIA or IA 35 or IB and IIB.
The active ingredients are used in a purity of from 90 to 100%, preferably from 95 to 100% (according to 1H-NMR or HPLC spectrum). 40 The compounds IA or IB, IIA and IIB or the mixtures or the corresponding formulations are applied by treating harmful fungi, their habitat or the materials, plants, seeds, soils, surfaces or spaces to be protected from fungal attack with a fungicidal amount of the mixture or of the compounds IA or IB and IIA or IA 45 or IB and IIB in the case of separate application. The treatment may be effected before or after infestation by the harmful fungi. 0050/45055 289867 24 The synergistic action of the novel mixtures can be demonstrated by the following experiments: Laboratory experiments: Effect of the novel mixtures on mycelium growth: Agar plates which contained the active ingredient were inoculated with mycelia of the fungi. The growth of the fungi was determined 10 after from 1 to 4 weeks, depending on the type of fungus, by comparison of the fungal colonies of an untreated control and the treated plates [diameter (cm) of the fungal colony is stated].
Harmful fungus Control X.8A-7 [200 ppm] IXA.l [100 ppm] I.8A-7 [200 ppm] IXA.l [100 ppm] Alternaria solani 8.5 7 8.5 3.6 Botrytis cinerea 8.5 8.5 8.5 6 Choanephora cucurbitarum 8.5 8.5 8.5 6.7 Cladosporium herbarum 4.5 0.7 3.1 0 Cylindrocarpon mali 4.2 1 3.7 0.6 Drechslera sigmoiduro 8.5 1.5 8.5 1.1 Drechslera teres 8.5 6.5 8.5 .4 Fusarium oxysporum 8 4 6.7 2.6 Gloeosporium fructigenum 8 3.4 7.8 2.7 Guignardia citricarpa 6 0.9 6.3 0 Monilinia spec. 6.3 .2 .7 0 Penicillium digitatum .7 3.1 .4 0 Penicillium expansum .5 3.8 3.7 Phomopsis lorgicola 8.5 3.5 7.1 2 Phytophthora cactorum 7.7 4.5 4.3 2.6 40 Pseudocercosporella herpotrichoides 4.4 1.8 4 0.3 Pyricularia oryzae 7.5 2.6 6.8 2.1 Phythium ultimun 8.5 8.5 6.3 .8 Rhizopus stolonifer 8.5 7.7 8.5 .5 45 Sclerotinia sclerotiorum 8.5 8.5 8.5 4.2 Sclerotium rolfsii 8.5 2.7 6.8 2.1 0050/45055 289867 :25 Harmful fungus Control i.8a-7 [200 ppm] iia. 1 [100 ppm] i.8a-7 [200 ppm] iia. 1 [100 ppm] Septoria nodorum . 6 3.5 4.8 2.7 Thielviopsis basicola 6.8 3.5 2.5 0.9 Venturia inaequalis 2.9 1.5 1.5 0 Verticilium dahliae 3.2 0.4 2.2 0 Spore germination test: Suspensions of fungal spores (Botrytis cinerea, 105 spores/ml) in microtiter plates were incubated for 24 hours at 18°C after the 15 addition of test solution. Thereafter, the germination was evaluated under a microscope by estimating the growth in comparison with untreated controls. The evaluation was based on the following rating: 0 plurality of spores not germinated (very good action) (+) spores germinated for the most part (< 5% mycelium growth) + > 5% to < 50% mycelium growth ++ > 50% to < 80% mycelium growth +-!•+ > 80% to < 100% mycelium growth (no action) 3£ 40 45 0050/45055 40 26 289867 45 I.2A-1 [ppm] IIB.5 [ppm] Evaluation - +++ - +++ - +++ - +++ - 50 ++ - 100 ++ +++ +++ ++ 50 + 100 + - - +++ I.2A-1 [ppm] IIA.1 [ppm] Evaluation - + - +++ - 50 +++ - 100 +++ ( + ) 50 ( + ) 100 0 - - +++ I.2A-1 [ppm] IIA.2 [ppm] Evaluation - + - +++ - 50 +++ - 100 ++ ( + ) 50 ( + ) 100 ( + ) - - +++ 0050/4i'055 289 27 I.2A-1 [ppm] IIA.3 [ppm] Evaluation - + - +++ - 50 +++ - 100 +++ + 50 ( + ) 100 0 - - +++ I.2A-1 [ppm] IIA.4 [ppm] Evaluation - + - +++ - 50 +++ - 100 ++ + 50 ( + ) 100 ( + ) - - +++ 40 I.2A-1 [ppm] IIA.5 [ppm] Evaluation - + - +++ - 50 +++ - 100 ++ + 50 + 100 ( + ) - - +++ 45 0050/45055 289867 28 I.2A-1 [ppm] IIA.6 [ppm] Evaluation - + - +++ - 50 +++ - 100 +++ + 50 + 100 + - - +++ I.2A-1 [ppm] IIA.7 [ppm] Evaluation - + - +++ - 50 +++ - 100 ++ ( + ) 50 0 100 0 - - +++ I.2A-1 [ppm] IIA.8 [ppm] Evaluation - + - +++ - 50 +++ - 100 +->• ( + ) 50 0 100 0 - - +++ Greenhouse experiments: The active ingredients were formulated as a 20 % strength emulsion in a mixture of 70 % by weight of cyclohexanone, 20 % by weight of Nekanil® LN (Lutensol® AP6, wetting agent having an emulsifying and dispersing action and based on ethoxylated alkylphenols) and 10 % by weight of Emulphor® EL (Emulan® EL, 0050/45055 28 9 86 29 emulsifier based on ethoxylated fatty alcohols) and were diluted with water to give the desired concentration.
Action against Botrytis cinerea (gray mold) Capsicum seedlings (Neusiedler Ideal Elite variety) having 4-5 leaves were sprayed to run-off with the active ingredient formulation. After the formulation had dried off, the plants were sprayed with a conidia suspension of the fungus Botrytis cinerea 10 and kept for 5 days at 22-24°C and high humidity. The evaluation was carried out visually.
I.2A-1 [ppm] IIA.l [ppm] Infestation [%] 250 - 18 125 - 8 63 - - 250 250 250 6 125 250 2 63 250 7 - - 45 Action against Botrytis cinerea (gray mold) Disks of green peppers were sprayed to run-off with the active 30 ingredient formulation. After the formulation had dried off, the disks were sprayed with a spore suspension of Botrytis cinerea (1.7x10s spores per ml of a 2 % strength biomalt solution) and kept for 4 days at 18°C and high humidity. The evaluation was carried out visually.
I.2A—1 [ppm] IIA.l [ppm] Infestation [%] 250 - 4 125 - 55 63 250 90 250 250 6 125 250 40 45 58 9 86 I.2A—1 [ppm] IIA.l [ppm] Infestation [%] 63 250 12 - - 95 I.2A-1 [ppm] IIB.5 [ppm] Infestation [%] 250 - 4 125 - 55 63 125 70 - 63 90 - 31 90 250 250 6 125 250 63 250 12 250 63 3 125 63 63 63 3 - - 95 Action against Puccinia recondita (wheat brown rust) Leaves of wheat seedlings (Kanzler variety) were dusted with spores of brown rust (Puccinia recondita). The plants thus treated were incubated for 24 hours at 20-22°C and 90-95 % relative humidity and then treated with the aqueous active ingredient formulation. After a further 8 days at 20-22°C and 65-70 % rela-35 tive humidity, the extent of fungal development was determined. The evaluation was carried out visually. 45

Claims (9)

0050/45055 31 289867 10 I.2A-1 [ppm] IIB.5 [ppm] Infestation [%] 250 - 15 125 - 20 63 - 25 - 125 30 - 63 40 - 31 30 250 250 1 125 250 3 63 250 5 250 63 5 125 63 5 63 63 15 - - 60 15 20 X.2A-1 [ppm] IIA.l [ppm] Infestation [ %] 250 - 4 125 - 55 63 - 50 - 250 90 250 250 6 125 250 10 63 250 12 - - 95 40 45 i 5 10 15 20 25 30 35 40 45 0050/45055 PCT/EP 95/02744 289867
1. A method for controlling harmful fungi, wherein the fungi, their habitat or the materials, plants, seed, soil, surfaces or spaces to be protected from fungal attack are treated jointly or separately at the same time or in succession with an active ingredient I of the formula IA or IB IA IB used [sic] where R' is -C[C02CH3]=CH0CH3, -C[C02CH3]=NOCH3, -C[CONHCH3]=NOCH3, -C[C02CH3]=CHCH3, -C[CO2CH3]=CHCH2CH3, -C[COCH3]=NOCH3, -C[C0CH2CH3]=N0CH3, -N(0CH3)-C02CH3, -N(CH3)-C02CH3 or -N(CH2CH3)-C02CH3, R" is a C-organic radical, which is bonded directly or.via an oxy, marcapto [sic], amino or alkylamino group, or together with a group X and the ring Q or T to which they are bonded, an unsubstituted or substituted bicyclic, partially or completely unsaturated system which, in addition to carbon ring members, may contain hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, Rx is -0C[C02CH3]=CH0CH3, -0C[C02CH3]=CHCH3, -0C[C02CH3]=CHCH2CH3, -SC[C02CH3]=CB0CH3, -SC[C02CH3]=CHCH3, -SC[C02CH3]=CHCH2CH3, -N(CH3)C[C02CH3]=CHOCH3, -N(CR3 )C[C02CH3 ] =N0CH3, -CH2C[C02CH3]=CH0CH3, -CH2C[C02CH3]=N0CH3 or -CH2C [CONHCH3]=N0CH3, Ri' is oxygen, sulfur, =CH- Oder =N~, n is 0, 1, 2 or 3, and the radicals X may be different when n is > 1, V 1 • x AMENDED SHEET f V ' IPEA / EP 5 10 15 20 25 30 35 40 45 0050/45055 PCT/EP 95/02744 33 X is cyano, nitro, halogen, Ci-C4-al [sic], Ci-C4~alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio or, where n is > 1, a C3-C5~alkylene, C3-C5-alkenylene, oxy-C2~C4- alkylene, oxy-Ci-C3-alkylene'oxy, oxy-C2_C4-alkenylene, oxy-C2~C4-alkenyleneoxy or butadienediyl group bonded to two adjacent carbon atoms of the phenyl ring, where these chains in turn may carry from one to three of the following radicals: halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci~C4-haloalkoxy or Ci-C4-alkylthio, Y is =C— or —N—, Q is phenyl, pyrrolyl, thienyl, furyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, triazolyl, pyridinyl, 2-pyridonyl, pyrimidinyl or triazinyl and T is phenyl, oxazolyl, thiazolyl, thiadiazolyl, oxadi-azolyl, pyridinyl, py::imidinyl or triazinyl, and a synergistic amount of a) an active ingredient of the formula IIA II HA R1 C NR2 OR3 where R1 is hydrogen, ci~Cio~alkyl, C2-Cio~alkenyl or C3-Cio-alkynyl, C3-C8-cycloalkyl or C4-Cs-cycloalkenyl, aryl, hetaryl, heterocyclyl, arylcarbonyl, het-arylcarbonyl, where the radicals may be partially or completely halogenated and/or may carry from one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, Ci-C6-alkyl, Ci-C6~haloalkyl, Ci~C6-alkyl-sulfonyl, Ci-C6-alkylsulfoxyl, Ci-Cg-alkoxy, Cx-Cg-haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci-C6~alkylthio, Ci-C6~alkylamino, ai-Cx-Cg-alkylamino, Ci-Cg-alkylaminocarbonyl, AMENDED SHEET IPEA / EP ' ; - "V, • r - 0050/45055 PCT/EP 95/02744 34 di-Ci-C6-alkylaminocarbonyl, ^cT-CfpalkTT- aminothiocarbonyl, di-Ci-Cg-alkylaminothio-carbonyl, C2-C6_alkenyl, C2-Cg-alkenyloxy or Ci'Cg-5 alkylcarbonyl, where these groups may he partially or completely halogenated, c3-c6~cycloalkyl, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy or hetarylthio, where these groups may foe par-10 tially or completely halogenated and/or may carry from one to three of the follov/ing radicals: cyano, nitro, hydroxyl, Ci~C4-alkyl, C!-C4-haloalkyl, Cr "J4-alkoxy, Ci-C4-haloalkoxy or C1-C4-alkylthio, 15 - C (^NOR1) -Ax-R11 where Ri,Ri;i- independently of one another a-^e each hydrogen or Ci-C6-alkyl, A is oxygen, sulfur, amino or alkyl- airtino and 20 x is 0 or 1, and R2 and R3 independently of one another are each hydrogen» Ci-Cg-alkyl or aryl 25 or a synergistic amount of b) an active ingredient of the formula 115 0 II IIB 30 Ra C NR13 Rc where Ra is phenyl, furyl, dihydropyranyl, oxathiinyl, ox^thiinyl dioxide, pyridyl, pyrazolyl or thiazolyl, where these 35 radicals may carry from one to three of the foll<2win9 substituents: halogen, Ci~C4-alkyl, Ci-C4-haloalkyi> C!-C4-alkoxy, Ci-C4-haloalkoxy or Ci~C4-alkylthio? Rb is hydrogen, Ci~C4-alkyl or Ci~C4-alkoxy; 40 Rc is phenyl or cyclohexyl, where these rings may partially or completely halogenated and/or may c<5-rrY from one to three of the following radicals: C1-C4-alk".yl/ C!-C4-haloalkyl, Ci-C.- alkoxy, Ci-C4- haloal.'.oxy Or 45 Ci~C4-alkylthio. AMENDED SHEET \ r , IPEA / EP ' \ v 0050/45055 PCT/E? 95/02744 10 20 289867 35
2. A synergistic mixture suitable for controlling harmful fungi and containing a solid or liquid carrier, an active ingredient of the formula I as claimed in claim 1/ and a synergistic amount of an active ingredient of the formula IIA as claimed in claim 1.
3. A synergistic mixture suitable for controlling harmful fungi and containing a solid or liquid carrier, an active ingredient of the formula I as claimed in claim 1, and a synergistic amount of an active ingredient of the formula IIB as claimed in claim 1.
4. Use or a compound IA or IB as claimed in claim 1 for the preparation of an agent suitable for controlling harmful 15 fungi, as claimed in claim 2 or 3. • .. ; "f- .
Use ox a compound IIA as claimed in claim 1 for.the. preparation of an agent suitable for controlling harmful; fungi, as claimed in claim 2. A '
6. Use of a compound IIB as claimed in claim 1 fox.-.thej prepaxa—
' - J.'. ■ «■*.*"• •* tion of an agent suitable for controlling harmful?-fungi p'f as -/ claimed in claim 4 . 25 7 . A method as claimed in claim 1, wherein an active*. Ingredient'?-^-:- ^ of the formula IA as claimed in claim 1 is used f or^iim^it*--.'^.-.-;-- _ ing the respiration at the cytochrome complex III. -V
A method as claimed in claim 1, wherein an active ingredient-5-.--^-.;'- " t./l. • V of the formula IB as claimed in claim 1 is used for inhibit-^ ing the respiration at the cytochrome complex III. _ .
9. An agent for carrying out the method as claimed in claim 1, which is conditioned in two parts, one part containing a com-35 pound of the formula la or lb in a solid or liquid carrier and the other part containing a compound of the formula Ila or lib as claimed in claim 1 in a solid or liquid carrier. 40 END OF CLAIMS 45 AMENDED SHEET IPEA / EP
NZ289867A 1994-07-21 1995-07-13 Fungicidal preparation and method using active compounds inhibiting respiration at the cytochrome complex iii NZ289867A (en)

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