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WO2007101547A2 - Combinaisons synergiques de principes actifs - Google Patents

Combinaisons synergiques de principes actifs Download PDF

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Publication number
WO2007101547A2
WO2007101547A2 PCT/EP2007/001466 EP2007001466W WO2007101547A2 WO 2007101547 A2 WO2007101547 A2 WO 2007101547A2 EP 2007001466 W EP2007001466 W EP 2007001466W WO 2007101547 A2 WO2007101547 A2 WO 2007101547A2
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WO
WIPO (PCT)
Prior art keywords
methyl
phenyl
trifluoromethyl
group
chloro
Prior art date
Application number
PCT/EP2007/001466
Other languages
German (de)
English (en)
Other versions
WO2007101547A3 (fr
Inventor
Rüdiger Fischer
Hans-Ludwig Elbe
Ralf Dunkel
Ulrike Wachendorff-Neumann
Anne Suty-Heinze
Peter Dahmen
Heike Hungenberg
Wolfgang Thielert
Bernd Springer
Original Assignee
Bayer Cropscience Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Cropscience Ag filed Critical Bayer Cropscience Ag
Publication of WO2007101547A2 publication Critical patent/WO2007101547A2/fr
Publication of WO2007101547A3 publication Critical patent/WO2007101547A3/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides

Definitions

  • the present invention relates to novel drug combinations which consist of a known phthalamide on the one hand and known fungicidal active compounds on the other hand and are very well suited for controlling undesirable pests such as insects and unwanted phytopathogenic fungi.
  • substituted halogenopyridines have fungicidal properties (compare DE-A1-196 46 407, EP-B-712 396).
  • Hal is chlorine, bromine or iodine
  • a 2 is NH or O
  • a 3 is N or CH
  • R 11 is in each case optionally monosubstituted or disubstituted by identical or different chlorine, cyano, methyl or trifluoromethyl-substituted phenyl, phenoxy or pyridinyl, or for 1- (4-chlorophenyl) -pyrazol-3-yl or for 1,2-propanedione bis (O-methyloxime) -1-yl,
  • R 12 is hydrogen or fluorine
  • Q is hydrogen or SH
  • n 0 or 1
  • R 13 is hydrogen, fluorine, chlorine, phenyl or 4-chlorophenoxy
  • R 14 is hydrogen or chlorine
  • R 15 and R 17 together then represent -CH 2 -CH 2 -CH [CH (CH 3 ) 2 ] - or -CH 2 -CH 2 -C (CH 3 ) 2 -,
  • a 5 is C or Si (silicon),
  • R 15 is hydrogen, hydroxy or cyano
  • R 16 represents 1-cyclopropylethyl, 1-chlorocyclopropyl, dC 4 alkyl, C, -C 6 hydroxyalkyl, C 1 -C 4 - alkylcarbonyl, Ci-C2 haloalkoxy-Ci-C 2 alkyl, trimethylsilyl-C r C 2 alkyl, monofluorophenyl, or phenyl,
  • R 15 and R 16 also together represent -Q-CH 2 -CH (R 18 ) -O-, -O-CH 2 -CH (R 18 ) -CH 2 -, or -O-CH- (2-chlorophenyl) - stand,
  • R 18 is hydrogen, C 1 -C 4 alkyl or bromine
  • R 19 is hydrogen or methyl
  • X is 2-chloro-3-pyridinyl; 1-methylpyrazol-4-yl which is substituted in the 3-position by methyl or byn-fluoromethyl and in the 5-position by hydrogen or chlorine, for 4-ethyl-2-ethylamino -l, 3-thiazol-5-yl, for 1-methyl-cyclohexyl, for 2,2-dichloro-l-ethyl-3-methyl-cyclopropyl, for 2-fluoro-2-propyl, 3,4- Dichloroisothiazol-5-yl, 5,6-dihydro-2-methyl-1,4-oxathim-3-yl, 4-methyl-1,2,3-thiadiazol-5-yl, 4,5-dimethyl 2-trimethylsilyl-thiophen-3-yl, 1-methylpyrrole
  • 3-yl which is substituted in the 4-position by methyl or T ⁇ fluormethyl and in the 5-position by hydrogen or chlorine, or represents phenyl which is monosubstituted to trisubstituted by identical or different chlorine, methyl or T ⁇ fluormethyl .
  • Y is substituted for a direct bond, optionally substituted by chlorine, cyano or oxo C 1 - C 6 alkanediyl (alkylene), C 2 -C 6 alkenediyl (alkenylene), or thiophenediyl, for hydrogen, Ci-C 6 -alkyl or the group
  • R 20 represents hydrogen, chlorine, cyano, C r C 6 -alkyl, by optionally mono- or disubstituted by identical or different chlorine or di (Ci-C 3 -alkyl) aminocarbonyl-substituted phenyl,
  • R 21 is hydrogen, chlorine or isopropoxy
  • R 22 is hydrogen, chlorine, hydroxyl, methyl, trifluoromethyl or di (C 1 -C 3 -alkyl) aminocarbonyl,
  • R 2Ü and R 21 also together represent * -CH (CH 3 ) -CH 2 -C (CH 3 ) 2 - or * -CH (CH 3 ) -O-
  • R 23 is benzyl, furyl or methoxymethyl
  • R 24 is methyl, cyclopropyl or 1-propynyl
  • R 25 and R 26 are each hydrogen or together are -O-CF 2 -O-,
  • R 27 is hydrogen, C 1 -C 4 -alkylaminocarbonyl or 3,5-dimethylisoxazol-4-ylsulfonyl,
  • R 28 is chloro, methoxycarbonylamino, chlorophenyl, furyl or thiazolyl
  • R 29 is n- or iso-propyl
  • R 30 is di (C 1 -C 2 -alkyl) aminoC 2 -C 4 -alkyl or diethoxyphenyl, wherein also salts of these compounds are included;
  • R and R independently of one another represent hydrogen or methyl
  • R 33 is C r C 4 alkyl (preferably C 12 -C, 4 alkyl), C 5 -C, 2 cycloalkyl (preferably C 10 -C 12 -Cycloal- alkyl), phenyl-Ci-C 4 alkyl which may be substituted in the phenyl moiety by halogen or C 1 -C 4 -alkyl, or by acrylyl which is substituted by chlorophenyl and dimethoxyphenyl; Group (16): Pyrroles of General Formula (XI)
  • R 34 is chlorine or cyano
  • R 35 is chlorine or nitro
  • R 36 is chlorine
  • R 35 and R 36 furthermore together represent -0-CF 2 -O-;
  • R 37 is phenyl, phenyl, 2-naphthyl, 1,2,3,4-tetrahydronaphthyl or indanyl unsubstituted or substituted by fluorine, chlorine, bromine, methyl or ethyl;
  • a 7 represents a direct bond or -O-
  • R 38 is hydrogen or C 1 -C 4 -alkyl
  • R 39 is C, -C 6 alkyl
  • R 40 is C, -C 6 alkyl or C 2 -C 6 alkenyl
  • R 41 is C 1 -C 6 -alkyl
  • R 40 and R 41 also together are C 4 -C 5 -alkanediyl (alkylene) which is monosubstituted or disubstituted by C 1 -C 6 -alkyl,
  • R 42 is bromine or chlorine
  • R 43 and R 47 independently of one another represent hydrogen, fluorine, chlorine or methyl
  • R 44 and R 46 independently of one another represent hydrogen or fluorine
  • R 45 is hydrogen, fluorine or methyl, Group (23): iodochromones of the general formula (XV)
  • R 4 is C 1 -C 6 -alkyl
  • R is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl;
  • R is hydrogen or fluorine
  • R 52 is hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl
  • Het stands for one of the following residues Hetl to Het7:
  • R 53 is iodine, methyl, difluoromethyl or trifluoromethyl
  • R 54 represents hydrogen, fluorine, chlorine or methyl, R is methyl, difluoromethyl or trifluoromethyl,
  • R is chlorine, bromine, iodine, methyl, difluoromethyl or trifluoromethyl
  • R 57 is methyl or trifluoromethyl.
  • the fungicidal action of the active ingredient combinations according to the invention is substantially higher than the sum of the effects of the individual active ingredients. So there is an unpredictable, true synergistic effect and not just an effect supplement.
  • insecticidal activity of the active compound combinations according to the invention is likewise substantially higher than the sum of the effects of the individual active compounds. So there is an unpredictable, true synergistic effect and not just an effect supplement.
  • the formula (I) comprises the following preferred mixing partners:
  • the formula (E) comprises the following preferred mixing partners of group (2):
  • the formula (ET) comprises the following preferred mixing partners of group (3):
  • the formula (IV) comprises the following preferred mixing partners of group (4):
  • Preferred mixing partners of group (5) are
  • the formula (V) comprises the following preferred mixing partners of group (6):
  • Penthiopyrad (known from EP-A 0 737 682) of the formula
  • Preferred mixing partners of group (7) are
  • Zinc ammoniate ethylenebis (dithiocarbamate) - poly (ethylenethiuram disulf ⁇ de)
  • the formula (VI) comprises the following preferred mixing partners of group (8):
  • the formula (VE) comprises the following preferred mixing partners of group (9):
  • the formula (VDI) comprises the following preferred mixing partners of group (10):
  • the formula (IX) comprises the following preferred mixing partners of group (11):
  • Preferred mixing partners of group (14) are:
  • the formula (X) comprises the following preferred mixing partners of group (15):
  • the formula (XI) comprises the following preferred mixing partners of group (16):
  • the formula (XS) comprises the following preferred mixing partners of group (18), which are known from WO 96/23793 and may each be present as E or Z isomers. Compounds of the formula (XS) can therefore be present as a mixture of different isomers or else in the form of a single isomer. Preference is given to compounds of the formula (XS) in the form of their E isomer:
  • Metrafenone (known from EP-A 0 897 904) of the formula
  • Ferimzone (known from EP-A 0 019 450) of the formula
  • Preferred mixing partners of group (20) are:
  • Preferred mixing partners of group (21) are:
  • Preferred mixing partners of the group (22) are:
  • Preferred mixing partners of group (24) are:
  • the compound (6-7) carpropamid has three asymmetric substituted carbon atoms.
  • the compound (6-7) may therefore be present as a mixture of different isomers or in the form of a single component. Particularly preferred are the compounds
  • (2-6) (2E) -2- (methoxyimino) -N-methyl-2- ⁇ 2 - [( ⁇ ) - ( ⁇ 1- [3- (trifluoromethyl) phenyl] ethoxy ⁇ imino) methyl] phenyl ⁇ ethanamide
  • (2-8) 5-methoxy-2-methyl-4- (2- ⁇ [( ⁇ (1E)) - 1 - [3- (trifluoromethyl) phenyl] ethylidene ⁇ - amino) oxy] methyl ⁇ phenyl) -2,4-dihydro-3H-l, 2,4-triazol-3-one
  • the following active ingredients are particularly preferred:
  • Preferred embodiments of the invention for treating seed are mixtures comprising (Ia) and fluoxastrobin (2-2) and / or trifloxystrobin (2-4) and / or prothioconazoles (3-15) and / or tebuconazoles (3-17) and / or ipconazole (3-18) and / or triticonazole (3-20) and / or triadimenol (3-22) and / or carpropamide (6-7) and / or N- [2- (1,3-dimethylbutyl ) phenyl] -5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide (6-18) and / or N- ⁇ 2- [3-chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl ⁇ -2- (trifluoromethyl) benzamide (6-25) and / or thiram (7-5) and / or metalaxyl (8-3) and / or metala
  • Highlighted embodiments of the invention for treating seed are furthermore mixtures comprising (Ib) and fluoxastrobin (2-2) and / or trifloxystrobin (2-4) and / or prothioconazoles (3-15) and / or tebuconazoles (3-17) and / or ipconazole (3-18) and / or triticonazole (3-20) and / or triadimenol (3-22) and / or carpropamide (6-7) and / or ⁇ - [2- (1,3-dimethylbutyl) phenyl] -5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide (6-18) and / or N- ⁇ 2- [3-chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl ⁇ -2- (trifluoromethyl) benzamide (6-25) and / or thiram (7-5) and / or metalaxyl (8-3) and / or
  • Preferred embodiments of the invention for treating seed are furthermore mixtures comprising (Ic) and fluoxastrobin (2-2) and / or trifloxystrobin (2-4) and / or prothioconazoles (3-15) and / or tebuconazoles (3-17) and / or ipconazole (3-18) and / or triticonazole (3-20) and / or triadimenol (3-22) and / or carpropamide (6-7) and / or ⁇ - [2- (1,3-dimethylbutyl) phenyl] -5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide (6-18) and / or N- ⁇ 2- [3-chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl ⁇ -2- (trifluoromethyl) benzamide (6-25) and / or thiram (7-5) and / or metalaxyl (8-3) and / or metal
  • the active compound combinations according to the invention contain, in addition to an active compound of the formula (I) from group 1, at least one active compound of the compounds of groups (2) to (24). You may also contain other fungicidal Zumischkomponenten. If the active ingredients in the active compound combinations according to the invention are present in certain weight ratios, the synergistic effect is particularly pronounced. However, the weight ratios of the active ingredients in the drug combinations can be varied within a relatively wide range.
  • the combinations according to the invention comprise active compounds of the formula (I) and a mixed partner from one of the groups 2 to 24 in the mixing ratios exemplified in the table below.
  • the mixing ratios are based on weight ratios.
  • the ratio is to be understood as the active ingredient of the formula (I): Mischpartner
  • Group (2) Strobilurins 100: 1 to 1 2000 50 1 to 1 1000
  • Group (3) Triazoles 100: 1 to 1 2000 50 1 to 1 1000
  • Group (6) carboxamides without (6-6) 100: 1 to 1 2000 50 1 to 1 1000
  • Group (9) Anilino-pyrimidines 500: 1 to 1 10 250 1 to 1 1
  • Group (11) Carbamate 500: 1 to 1 10 250 1 to 1 1
  • Dithianone 500 1 to 1 10 250 1 to 1 1
  • Metrafenone 125 1 to 1 2000 50 1 to 1 1000
  • the mixing ratio should be such that a synergistic mixture is obtained.
  • the mixing ratios between the compound of formula (I) and a compound of any one of groups (2) to (24) may also vary between the individual compounds of a group.
  • the active compound combinations according to the invention have very good fungicidal properties and can be used for controlling phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc.
  • the active compound combinations according to the invention are particularly suitable for controlling Phytophthora infestans, Plasmopara viticola and Botrytis cinerea.
  • the active compound combinations according to the invention have a strong microbicidal action and can be used for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.
  • Fungicides can be used for the control of Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Blumeria species such as Blumeria graminis
  • Podosphaera species such as Podosphaera leucotricha
  • Sphaerotheca species such as Sphaerotheca fuliginea
  • Uncinula species such as Uncinula necator
  • Gymnosporangium species such as Gymnosporangium sabinae
  • Hemileia species such as Hemileia vastatrix
  • Phakopsora species such as Phakopsora pachyrhizi and Phakopsora meibomiae
  • Puccinia species such as Puccinia recondita
  • Uromyces species such as Uromyces appendiculatus
  • Bremia species such as Bremia lactucae
  • Peronospora species such as Peronospora pisi or P. brassicae;
  • Phytophthora species such as Phytophthora infestans
  • Plasmopara species such as Plasmopara viticola
  • Pseudoperonospora species such as Pseudoperonospora humuli or
  • Pythium species such as Pythium ultimum
  • Alternaria species such as Alternaria solani;
  • Cercospora species such as Cercospora beticola
  • Cladiosporum species such as Cladiosporium cucumerinum
  • Cochliobolus species such as Cochliobolus sativus
  • Colletotrichum species such as Colletotrichum lindemuthanium
  • Cycloconium species such as cycloconium oleaginum
  • Diaporthe species such as Diaporthe citri;
  • Elsinoe species such as Elsinoe fawcettii
  • Gloeosporium species such as, for example, Gloeosporium laeticolor
  • Glomerella species such as Glomerella cingulata
  • Guignardia species such as Guignardia bidwelli
  • Leptosphaeria species such as Leptosphaeria maculans
  • Magnaporthe species such as Magnaporthe grisea
  • Mycosphaerella species such as Mycosphaerelle graminicola
  • Phaeosphaeria species such as Phaeosphaeria nodorum
  • Pyrenophora species such as, for example, Pyrenophora teres
  • Ramularia species such as Ramularia collo-cygni
  • Rhynchosporium species such as Rhynchosporium secalis
  • Septoria species such as Septoria apii
  • Typhula species such as Typhula incarnata
  • Venturia species such as Venturia inaequalis
  • Corticium species such as Corticium graminearum
  • Fusarium species such as Fusarium oxysporum
  • Gaeumannomyces species such as Gaeumannomyces graminis
  • Rhizoctonia species such as Rhizoctonia solani
  • Tapesia species such as Tapesia acuformis
  • Thielaviopsis species such as Thielaviopsis basicola
  • Ear and panicle diseases caused by e.g.
  • Alternaria species such as Alternaria spp .
  • Aspergillus species such as Aspergillus flavus
  • Cladosporium species such as Cladosporium spp .
  • Claviceps species such as Claviceps purpurea; Fusarium species such as Fusarium culmorum;
  • Gibberella species such as Gibberella zeae
  • Monographella species such as Monographella nivalis
  • Sphacelotheca species such as Sphacelotheca reiliana
  • Tilletia species such as Tilletia caries
  • Urocystis species such as Urocystis occulta
  • Ustilago species such as Ustilago nuda
  • Aspergillus species such as Aspergillus flavus
  • Botrytis species such as Botrytis cinerea
  • Penicillium species such as Penicillium expansum
  • Sclerotinia species such as Sclerotinia sclerotiorum
  • Verticilium species such as Verticilium alboatrum
  • Fusarium species such as Fusarium culmorum
  • Phytophthora species such as Phytophthora cactorum
  • Pythium species such as Pythium ultimum
  • Rhizoctonia species such as Rhizoctonia solani
  • Sclerotium species such as Sclerotium rolfsü
  • Nectria species such as Nectria galligena
  • Monilinia species such as Monilinia laxa
  • Taphrina species such as Taphrina deformans
  • Esca species such as Phaemoniella clamydospora
  • Botrytis species such as Botrytis cinerea
  • Rhizoctonia species such as Rhizoctonia solani
  • Xanthomonas species such as Xanthomonas campestris pv. Oryzae;
  • Pseudomonas species such as Pseudomonas syringae pv. Lachrymans;
  • Erwinia species such as Erwinia amylovora
  • the following diseases of soybean beans can be controlled:
  • Alternaria leaf spot (Alternaria spec. Atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. Truncatum), Brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)) , Dactuliophora leaf spot (Dactuliophora glycines), Downy Mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), Frogeye leaf spot (Cercospora sojina), Leptosphaerulina Leaf Spot (Leptosphaerulina trifolii), Phyllostica leaf spot (Phyllosticta sojaecola), Powdery Mildew (Phyllosticta sojaecola) Micros
  • Black Root Red (Calonectria crotalariae), Charcoal Red (Macrophomina phaseolina), Fusarium Blight or Wiit, Root Red, and Pod and Collar Red (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus Root Red (Mycoleptodiscus terrestris), Neocosmospora (Neocosmopspora vasinfecta), Pod and Star Blight (Diaporthe phaseolorum), Star Canker (Diaporthe phaseolorum var.
  • Phytophthora red (Phytophthora megasperma), Brown Stem Red (Phialophora gregata), Pythium Red (Pythium aphanidermatum, Pythium irregular, Pythium Debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Red, Stem Decay, and Damping Off (Rhizoctonia solani), Sclerotinia Stem Decay (Sclerotinia sclerotiorum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Red (Thielaviopsis basicola).
  • the good plant tolerance of the active compound combinations in the concentrations necessary for controlling plant diseases allows treatment of whole plants (above-ground parts of plants and roots), of planting and seed, and of the soil.
  • the active compound combinations according to the invention can be used for foliar application or as a mordant.
  • the good plant tolerance of the usable active ingredients in the necessary concentrations for controlling plant diseases allows treatment of the seed.
  • the active compounds according to the invention can thus be used as mordants.
  • methods for treating seed should also include the intrinsic fungicidal properties of transgenic plants in order to achieve optimum protection of the seed and the germinating plant with a minimum of pesticide use.
  • the present invention therefore more particularly relates to a method of protecting seeds and germinating plants from the infestation of phytopathogenic fungi by treating the seed with an agent according to the invention.
  • the invention also relates to the use of the seed treatment agents of the invention for protecting the seed and the germinating plant from phytopathogenic fungi.
  • the invention relates to seed which has been treated with an agent according to the invention for protection against phytopathogenic fungi.
  • One of the advantages of the present invention is that because of the particular systemic properties of the compositions of the invention, treatment of the seed with these agents not only protects the seed itself, but also the resulting plants after emergence from phytopathogenic fungi. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
  • mixtures according to the invention can also be used in particular in the case of transgenic seed.
  • compositions according to the invention are suitable for the protection of seeds of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture.
  • these are seeds of cereals (such as wheat, barley, rye, millet and oats),
  • cereals such as wheat, barley, rye and oats
  • corn and rice are particularly important.
  • the agent according to the invention is applied to the seed alone or in a suitable formulation.
  • the seed is in a suitable formulation.
  • the seed is in a suitable formulation.
  • Flasks, shells, stems, shell, wool or pulp was freed.
  • seeds can be used that have been harvested, cleaned and up to a moisture content of below
  • Drying e.g. treated with water and then dried again.
  • the agents according to the invention can be applied directly, ie without containing further components and without being diluted.
  • suitable formulations and methods for seed treatment are known to those skilled in the art and are described e.g. in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430 A, US 5,876,739 A, US 2003/0176428 A1, WO 2002/080675 A1, WO 2002/028186 A2.
  • the active compound combinations according to the invention are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.
  • the active compound combinations according to the invention also have a strong tonic effect in plants. They are therefore suitable for mobilizing plant-own defenses against attack by unwanted microorganisms.
  • plant-strengthening (resistance-inducing) substances are to be understood as meaning those substances which are capable of stimulating the defense system of plants in such a way that the treated plants exhibit extensive resistance to these microorganisms with subsequent inoculation with undesired microorganisms.
  • Undesirable microorganisms in the present case are phytopathogenic fungi, bacteria and viruses.
  • the substances according to the invention can therefore be used to protect plants within a certain period of time after the treatment against the infestation by the said pathogens.
  • the period within which protection is provided generally extends from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the active ingredients.
  • the good plant compatibility of the active compound combinations in the concentrations necessary for controlling plant diseases allows a treatment of aboveground plant parts, of plant and seed, and the soil.
  • the active compound combinations according to the invention can be used to combat cereal diseases, such as, for example, with particularly good results. against Puccinia species and diseases in wine, fruit and vegetable crops, such as against Botrytis, Venturia or Alternaria species.
  • the active compound combinations according to the invention are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.
  • the active compound combinations according to the invention can also be used in certain concentrations and application rates as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of other active ingredients.
  • plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights.
  • Plant parts are to be understood as meaning all aboveground and subterranean parts and organs of the plants, such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the active ingredient combinations is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, eg by dipping, spraying, evaporating, atomizing, spreading, spreading and propagating material, in particular in the case of seeds single or multi-layer coating.
  • the active ingredient combinations can be prepared before the treatment by mixing the individual active ingredients.
  • the treatment is carried out successively by using first a phthalamide of the group (1) followed by the treatment with an active ingredient of the groups (2) to (24).
  • the active compound combinations according to the invention can be used to protect industrial materials against infestation and destruction by undesired microorganisms.
  • Technical materials as used herein mean non-living materials that have been prepared for use in the art.
  • technical materials to be protected from microbial alteration or destruction by the active compounds of the invention may be adhesives, glues, paper and board, textiles, leather, wood, paints and plastics, coolants and other materials that may be infested or degraded by microorganisms .
  • materials to be protected are also parts of production plants, such as cooling water circuits, called, which can be affected by the proliferation of microorganisms.
  • technical materials which may be mentioned are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer fluids, particularly preferably wood.
  • microorganisms that can cause degradation or a change in the technical materials, for example, bacteria, fungi, yeasts, algae and mucus organisms may be mentioned.
  • the active compounds according to the invention preferably act against fungi, in particular molds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • microorganisms of the following genera There may be mentioned, for example, microorganisms of the following genera:
  • Alternaria such as Alternaria tenuis
  • Aspergillus such as Aspergillus niger
  • Chaetomium such as Chaetomium globosum, Coniophora, like Coniophora puetana,
  • Lentinus like Lentinus tigrinus
  • Penicillium such as Penicillium glaucum
  • Polyporus such as Polyporus versicolor
  • Aureobasidium such as Aureobasidium pullulans
  • Sclerophoma such as Sclerophoma pityophila
  • Trichoderma like Trichoderma viride
  • Escherichia like Escherichia coli
  • Pseudomonas such as Pseudomonas aeruginosa
  • Staphylococcus such as Staphylococcus aureus.
  • the active compound combinations according to the invention also have very good antifungal effects. They have a very broad antimycotic spectrum of activity, in particular against dermatophytes and yeasts, mold and diphasic fungi (for example against Candida species such as Candida albicans, Candida glabrata) as well as Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, microsporon species such as Microsporon canis and audouinii.
  • Candida species such as Candida albicans, Candida glabrata
  • Epidermophyton floccosum Aspergillus species such as Aspergillus niger and Aspergillus fumigatus
  • Trichophyton species such as Trichophyton mentagrophytes
  • microsporon species such as Microsporon canis and audouinii.
  • the list of these fungi is by no means a limitation
  • the active compound combinations can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules.
  • the application is done in the usual way, e.g. by pouring, spraying, spraying, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient itself into the soil. It can also be the seed of the plants to be treated.
  • the application rates can be varied within a relatively wide range, depending on the mode of administration.
  • the application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
  • the application rates of active ingredient are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • the listed plants can be treated particularly advantageously according to the invention with the active ingredient mixtures.
  • the preferred ranges given above for the active compounds or mixtures also apply to the treatment of these plants. Particularly emphasized is the plant treatment with the compounds or mixtures specifically mentioned in the present text.
  • the active compound combinations according to the invention are also suitable for controlling animal pests, preferably arthropods and nematodes, in particular nematodes and insects, which occur in agriculture, animal health, in forests, in the protection of stored products and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • animal pests preferably arthropods and nematodes, in particular nematodes and insects, which occur in agriculture, animal health, in forests, in the protection of stored products and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include:
  • Chilopoda e.g. Geophilus carpophagus, Scutigera spp.
  • Symphyla e.g. Scutigerella immaculata.
  • Thysanura e.g. Lepisma saccharina.
  • Orthoptera e.g. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
  • Phthiraptera for example, Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp. From the order of Thysanoptera eg Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.
  • Heteroptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
  • Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis Spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria me
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp.
  • arachnids e.g. Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.
  • Chorioptes spp. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp.
  • the plant parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.
  • the active ingredient combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, foams, dusts, pastes, soluble powders, granules, aerosols, suspension emulsions Concentrates, active substance impregnated natural and synthetic substances, ultra-fine encapsulations in polymeric materials and in shell materials for seeds, as well as ULV-KaIt and warm mist formulations.
  • formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Suitable solid carriers are: For example, ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic minerals, such as finely divided silica, alumina and silicates, as solid carriers for granules in question: eg broken and fractionated natural rocks such Calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydro
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids may be used in the formulations.
  • Other additives may be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
  • the active compound combinations according to the invention can be present in commercial formulations and in the formulations prepared from these formulations in admixture with other active ingredients, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • the insecticides include, for example, phosphoric acid esters, carbamates, carboxylic esters, chlorinated hydrocarbons, phenylureas, microorganism-produced substances and the like.
  • the active compound combinations according to the invention may also be present when used as insecticides in their commercial formulations as well as in the formulations prepared from these formulations in admixture with synergists.
  • Synergists are compounds, through which the effect of the active ingredients is increased, without the added synergist itself must be active.
  • the active substance content of the application forms prepared from the commercial formulations can vary within wide ranges.
  • the active ingredient concentration of the use forms may be from 0.0000001 to 95% by weight of active ingredient, preferably between 0.0001 and 1% by weight.
  • the application is done in a custom forms adapted to the application forms.
  • the drug combinations When used against hygiene and storage pests, the drug combinations are characterized by an excellent Residual Sign on wood and clay and by a good alkali stability on limed substrates.
  • the active compound combinations according to the invention not only act against plant, hygiene and storage pests, but also in the veterinary sector against animal parasites such as ticks, leather ticks, mange mites, runny mites, flies (stinging and licking), parasitic fly larvae, lice, Hair pieces, featherlings and fleas.
  • animal parasites such as ticks, leather ticks, mange mites, runny mites, flies (stinging and licking), parasitic fly larvae, lice, Hair pieces, featherlings and fleas.
  • parasites include:
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
  • Trimenopon spp. Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.
  • Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp , Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp.,
  • Morellia spp. Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,
  • siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
  • heteropterid e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
  • Actinedida Prostigmata
  • Acaridida e.g. Acarapis spp., Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp , Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Rnemidocoptes spp., Cytodites spp., Laminosioptes spp.
  • the active compound combinations according to the invention are also suitable for controlling arthropods which are farm animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, caged birds, aquarium fish and so-called experimental animals, such. Hamsters, guinea pigs, rats and mice.
  • arthropods are farm animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, caged birds, aquarium fish and so-called experimental animals, such. Hamsters, guinea pigs, rats and mice.
  • enteral administration in the form of, for example, tablets, capsules, infusions, Drenchen, granules, pastes, BoIi, the feed-through process, suppositories
  • parenteral administration such as by Injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants
  • nasal application by dermal application in the form of, for example, dipping or bathing (dipping), spraying (spray), pouring (pour-on and spot-on), washing , powdering and with the aid of active ingredient-containing shaped bodies, such as collars, ear tags, tail marks, limb bands, holsters, marking devices, etc.
  • the active ingredient combinations When used for livestock, poultry, pets, etc., the active ingredient combinations may be used as formulations (for example, powders, emulsions, flowables) containing the active ingredients in an amount of 1 to 80% by weight, directly or after 100 to 10,000 dilution or use as a chemical bath.
  • formulations for example, powders, emulsions, flowables
  • insects which destroy industrial materials.
  • insects are mentioned:
  • Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.
  • Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
  • Non-living materials such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.
  • the material to be protected from insect attack is wood and woodworking products.
  • Wood and woodworking products which can be protected by the composition or mixtures according to the invention are to be understood by way of example: lumber, wooden beams, railway sleepers, bridge parts, boat jetties, wooden vehicles, crates, pallets, containers, telephone poles, wooden cladding, wooden windows and doors , Plywood, chipboard, carpentry or wood products that are commonly used in building or joinery.
  • the active compound combinations can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
  • the formulations mentioned can be prepared in a manner known per se, for example by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersing and / or binding or fixing agent, water repellent, optionally siccatives and UV stabilizers and optionally Dyes and pigments and other processing aids.
  • the insecticidal compositions or concentrates used for the protection of wood and wood-based materials contain the active compound according to the invention in a concentration of from 0.0001 to 95% by weight, in particular from 0.001 to 60% by weight.
  • the amount of agents or concentrates used depends on the nature and occurrence of the insects and on the medium.
  • the optimal amount used can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active ingredient, based on the material to be protected.
  • the solvent and / or diluent used is an organic-chemical solvent or solvent mixture and / or an oily or oily high-volatile organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agent.
  • organic-chemical solvents are preferably oily or oily solvents having an evaporation number above 35 and a flash point above 30 0 C, preferably above 45 0 C used.
  • water-insoluble, oily and oily solvents corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene are used.
  • Mineral oils having a boiling range of 170 to 220 0 C, white spirit having a boiling range of 170 to 220 0 C., spindle oil with a boiling range of 250 to 350 0 C, petroleum and aromatics with a boiling range of 160 to 280 0 C, oil of turpentine and Like. For use.
  • liquid aliphatic hydrocarbons having a boiling range from 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons having a boiling range from 180 to 220 ° C. and / or spindle oil and / or monochloronaphthalene, preferably ⁇ -monochloronaphthalene, are used ,
  • the organic non-volatile oily or oily solvents having an evaporation number above 35 and a flash point above 30 0 C, preferably above 45 ° C, can be partially replaced by light or medium volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flash point above 30 0 C, preferably above 45 ° C, and that the mixture in this solvent mixture is soluble or emulsifiable.
  • a part of the organic-chemical solvent or solvent mixture or an aliphatic polar organic-chemical solvent or solvent mixture is replaced.
  • aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups are used, for example glycol ethers, esters or the like.
  • organic-chemical binders are the water-dilutable and / or soluble or dispersible or emulsifiable synthetic resins and / or binding drying oils used in the organic-chemical solvents used, in particular binders consisting of or containing an acrylate resin, a vinyl resin, eg Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or or synthetic resin used.
  • binders consisting of or containing an acrylate resin, a vinyl resin, eg Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene coumarone resin
  • the synthetic resin used as the binder may be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water repellents, odor correctors and inhibitors or corrosion inhibitors and the like can be used.
  • At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably present as the organic-chemical binder in the middle or in the concentrate.
  • Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
  • the mentioned binder can be completely or partially replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. Preferably, they replace 0.01 to 30% of the binder (based on 100% of the binder used).
  • the plasticizers are derived from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric esters such as tributyl phosphate, adipic acid esters such as di (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerol ethers or higher molecular weight glycol ethers, glycerol esters and p-toluenesulfonic acid ester.
  • phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate
  • phosphoric esters such as tributyl phosphate
  • adipic acid esters such as di (2-ethylhexyl) adipate
  • stearates such as butyl
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
  • water is also suitable as the solvent or diluent, if appropriate in admixture with one or more of the abovementioned organochemical solvents or diluents, emulsifiers and dispersants.
  • wood protection is provided by large scale impregnation methods, e.g. Vacuum, double vacuum or printing process achieved.
  • the active compound combinations according to the invention can be used to protect against fouling of objects, in particular of hulls, sieves, nets, structures, quays and signal systems, which come into contact with seawater or brackish water.
  • sessile oligochaetes such as limeworm worms, shells and species of the group Ledamorpha (barnacles), such as various Lepas and scalpelum species, or species of the group Balanomorpha (barnacles), such as Baianus or Pollicipes species
  • barnacles such as various Lepas and scalpelum species
  • Balanomorpha such as Baianus or Pollicipes species
  • Ectocarpus sp. and Ceramium sp. is particularly the fouling by sessile Entomostraken groups, which are summarized under the name Cirripedia (cirripeds), particular importance.
  • the use of heavy metals e.g. in bis (trialkyltin) sulfides, tri-n-butyltin laurate, tri-w-butyltin chloride, copper (T) oxide, triethyltin chloride, tri-n-butyl (2-phenyl-4-chlorophenoxy) -tin, tributyltin oxide, molybdenum disulfide, Antimony oxide, polymeric butyl titanate, phenyl (bispyridine) bismuth chloride, tri-n-butyltin fluoride, manganese ethylene bis-thiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bis-thiocarbamate, zinc and copper salts of 2-pyridinethiol-1-oxide, bisdimethyldithiocarbamoylzinc ethylene bisthiocarbamate, zinc oxide, copper Q ethylene. bisdithioc
  • the ready-to-use antifouling paints may optionally contain other active substances, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
  • Suitable combination partners for the antifouling agents according to the invention are preferably: Algicides such as 2-fer ⁇ -butylamino-4-cyclopropylamino-6-methylthio-l, 3,5-triazine, dichlorophene, diuron, endothal, fentin acetate, isoproturon, methabenzothiazuron, oxyfluorfen, quinoclamine and terbutryn;
  • Algicides such as 2-fer ⁇ -butylamino-4-cyclopropylamino-6-methylthio-l, 3,5-triazine, dichlorophene, diuron, endothal, fentin acetate, isoproturon, methabenzothiazuron, oxyfluorfen, quinoclamine and terbutryn;
  • Fungicides such as benzo [6] thiophenecarboxylic acid cyclohexylamide-S, S-dioxide, dichlofluanid, fluoro-folpet, 3-iodo-2-propynyl-butylcarbamate, tolylfluanid and azoles, e.g. Azaconazole, Cyproconazole, Epoxyconazole, Hexaconazole, Metconazole, Propiconazole and Tebuconazole;
  • Molluscicides such as fentin acetate, metaldehyde, methiocarb, niclosamide, thiodicarb and trimetharbarb;
  • antifouling agents such as 4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatrylsulfone, 2- (N, N-dimethylthiocarbamoylthio) -5-nitro thiazyl, potassium, copper, sodium and zinc salts of 2-pyridinethiol-1-oxide, pyridine-triphenylborane, tetrabutyldistannoxane, 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine, 2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiouram disulfide and 2,4,6-Trichlo ⁇ henylmaleinimid.
  • the antifouling agents used contain the active compound combinations according to the invention in a concentration of 0.001 to 50 wt .-%, in particular from 0.01 to 20 wt .-%.
  • the antifouling agents of the invention further contain the usual ingredients, e.g. in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.
  • Antifouling paints contain, in addition to the algicidal, fungicidal, molluscicidal and insecticidal active compounds according to the invention, in particular binders.
  • Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, especially in an aqueous system, vinyl chloride / vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene / styrene / acrylonitrile Rubbers, drying oils, such as linseed oil, rosin esters or modified hard resins in combination with tar or bitumen, asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.
  • paints also contain inorganic pigments, organic pigments or dyes which are preferably insoluble in seawater.
  • paints may contain materials such as rosin to allow for controlled release of the active ingredients.
  • the paints may further contain plasticizers, rheology modifiers, and other conventional ingredients. Also in soap Polishing antifouling systems, the compounds of the invention or the above mixtures can be incorporated.
  • insects in particular insects, arachnids and mites, which are used in enclosed spaces, such as, for example, apartments, factory halls, offices, vehicle cabins and the like. occurrence. They can be used to control these pests in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:
  • Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
  • Opiliones e.g. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
  • Zygentoma e.g. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
  • Diptera e.g. Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys Calcitrans, Tipula paludosa.
  • Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
  • Ctenocephalides canis Ctenocephalides felis
  • Pul ex irritans Tunga penetrans
  • Xenopsylla cheopis e.g. Ctenocephalides canis, Ctenocephalides felis, Pul ex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • Heteroptera e.g. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
  • Application is in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-less or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in straw baits or bait stations.
  • Pump and atomizer sprays misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-less or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in straw baits or bait stations.
  • plants and parts of plants can be treated.
  • plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights.
  • Under plant parts all above-ground and subterranean parts and organs of the plants such as shoot, leaf, flower and root are understood, by way of example, leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds and roots, tubers and rhizomes.
  • the plant parts also include crops as well as vegetative and generative propagation material, for example cuttings, tubers, rhiomes, offshoots and seeds.
  • plants and their parts can be treated.
  • wild-type or plant species obtained by conventional biological breeding methods such as crossing or protoplast fusion
  • plant cultivars and their parts are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the term “parts” or “parts of plants” or “plant parts” has been explained above.
  • the treatment according to the invention may also result in superadditive ("synergistic") effects.
  • superadditive for example, reduced application rates and / or extensions of the activity spectrum and / or a Enhancement of the effect of the substances and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salt content, increased flowering efficiency, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the actual expected effects.
  • the preferred plants or plant varieties to be treated according to the invention for transgenic (genetically engineered) plants include all plants which have obtained genetic material by the genetic engineering modification which gives these plants particularly advantageous valuable properties ("traits") Examples of such properties are better Plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or soil salt content, increased flowering efficiency, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, as against insects, mites, phytopathogenic fungi, bacteria and / or viruses and increased tolerance of the plants to certain herbicidal active substances.
  • transgenic plants include the important crops such as cereals (wheat, rice), corn, soy, potato, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soy, potato, cotton and oilseed rape.
  • Traits which are particularly emphasized are the increased defense of the plants against insects by toxins which are formed in the plants, in particular those which are produced by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), CryIA (b), Cry ⁇ A (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and combinations thereof) are produced in the plants (hereinafter, 3t plants ").
  • Traits which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example "PAT” gene).
  • the genes conferring the desired properties (“traits") may also be present in combinations with one another in the transgenic plants.
  • “Bt plants” are maize varieties, cotton varieties, soybean varieties and potato varieties sold under the trade names YIELD GARD® (eg Corn, cotton, soy), KnockOut® (eg corn), StarLink® (eg corn), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato).
  • herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, cotton, soya), Liberty Link® (tolerance to phosphinotricin, eg rapeseed), IMI® (tolerance to Lmdazolinone) and STS® (tolerance to sulfonylureas eg corn).
  • Herbicide-resistant (conventionally grown on herbicide tolerance) plants are also the varieties marketed under the name Clearfield® (eg corn) mentioned. Of course, these statements also apply to future or future marketed plant varieties with these or future developed genetic traits.
  • the plants listed can be treated particularly advantageously according to the invention with the erfmdungsge- proper drug mixtures.
  • the preferred ranges given above for the mixtures also apply to the treatment of these plants.
  • Particularly emphasized is the plant treatment with the mixtures specifically mentioned in the present text.
  • the good insecticidal and fungicidal action of the active compound combinations according to the invention is evident from the examples below. While the individual active ingredients have weaknesses in their effect, the combinations show an effect that goes beyond a simple sum of effects. A synergistic effect is always present in the case of insecticides and fungicides if the insecticidal or fungicidal action of the active substance combinations is greater than the sum of the effects of the individually applied active substances.
  • X means the degree of killing or efficiency, expressed in% of the untreated control, when using the active compound A at a rate of application of mppm or g / ha,
  • Y means the degree of killing or efficiency, expressed in% of the untreated control, when using the active ingredient B in an application rate of nppm or g / ha, and
  • E is the degree of kill or efficiency expressed as% of untreated control
  • the degree of kill or efficiency is determined in%. It means 0% a degree of kill or efficiency equal to that of the control, while a kill rate of 100% means that all animals are dead and an efficiency of 100% means that no infestation is observed.
  • the effect of the combination is over-additive, i. there is a synergistic effect.
  • the actual observed efficiency must be greater than the expected efficiency value (E) calculated from the above formula.
  • Example A The invention is illustrated by the following examples. However, the invention is not limited to the examples.
  • Example A The invention is illustrated by the following examples. However, the invention is not limited to the examples.
  • the microtest is performed in microtiter plates with Potato Dextrose Broth (PDB) as a liquid test medium.
  • PDB Potato Dextrose Broth
  • the application of the active ingredients is carried out as a technical a.i., dissolved in acetone.
  • a spore suspension of Penicillium brevicaule is used for inoculation.
  • 0% means an efficiency which corresponds to the growth in the controls, while an efficiency of 100% means that no fungal growth is observed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Cotton leaves which are heavily infested with the cotton aphid (Aphis gossypii) are treated by being dipped into the preparation of active compound of the desired concentration.
  • the defrost is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • the determined kill values are calculated according to the Colby formula.

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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)

Abstract

L'invention concerne de nouvelles combinaisons de principes actifs qui sont constituées d'un phtalamide de formule (I), dans laquelle Hal représente chlore, brome ou iode et * représente un atome de carbone en configuration R ou S, de préférence en configuration S, ainsi que des groupes de principes actifs (1) à (24) présentés dans la description. Ces combinaisons de principes actifs présentent d'excellentes propriétés insecticides et fongicides.
PCT/EP2007/001466 2006-03-06 2007-02-21 Combinaisons synergiques de principes actifs WO2007101547A2 (fr)

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DE102006010202 2006-03-06
DE102006010202.9 2006-03-06
DE102006037120A DE102006037120A1 (de) 2006-03-06 2006-08-09 Synergistische Wirkstoffkombinationen
DE102006037120.8 2006-08-09

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CL (1) CL2007000571A1 (fr)
DE (1) DE102006037120A1 (fr)
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WO2008077925A1 (fr) * 2006-12-22 2008-07-03 Bayer Cropscience Ag Composition pesticide comprenant du propamocarbe-fosétylate et une substance active insecticide
WO2008077930A2 (fr) * 2006-12-22 2008-07-03 Bayer Cropscience Ag Composition pesticide comprenant du fosétyl-aluminium et une substance active insecticide
WO2008077922A3 (fr) * 2006-12-22 2008-09-18 Bayer Cropscience Ag Composition pesticide contenant de la fénamidone et un composé insecticide
CN101755795A (zh) * 2009-11-17 2010-06-30 陕西汤普森生物科技有限公司 一种含氟铃脲和氟虫双酰胺的增效杀虫组合物
US20100227900A1 (en) * 2009-02-03 2010-09-09 Bayer Cropscience Ag Use of Sulphur-Containing Heteroaromatic Acid Analogues as Bactericides
EP2239331A1 (fr) * 2009-04-07 2010-10-13 Bayer CropScience AG Procédé pour améliorer l'utilisation du potentiel de production dans des plantes transgéniques
US8216971B2 (en) 2006-12-22 2012-07-10 Bayer Intellectual Property Gmbh Pesticide composition comprising propamocarb-hydrochloride and an insecticide active substance
CN103068236A (zh) * 2010-06-30 2013-04-24 拜耳知识产权有限责任公司 包含氟唑菌苯胺的协同活性成分结合物
WO2014170354A1 (fr) * 2013-04-19 2014-10-23 Bayer Cropscience Ag Combinaisons synergiques insecticides et/ou fongicides de dérivés d'acide diamide phtalique et d'un autre ingrédient actif
JP2014530182A (ja) * 2011-09-16 2014-11-17 バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー 植物収量を向上させるためのアシルスルホンアミド類の使用
CN105307493A (zh) * 2013-03-05 2016-02-03 拜耳作物科学股份公司 酰基磺酰胺用于提高植物产量的用途
WO2021064252A1 (fr) 2019-10-05 2021-04-08 JEUNEN, Carlo Synergiste de pesticides sx-pyr
US12114660B2 (en) 2014-12-30 2024-10-15 Corteva Agriscience Llc Picolinamide compounds with fungicidal activity

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WO2008122396A2 (fr) * 2007-04-04 2008-10-16 Syngenta Participations Ag Procédé d'amélioration de croissance de plante
EP2481284A3 (fr) * 2011-01-27 2012-10-17 Basf Se Mélanges de pesticides
TWI774761B (zh) * 2017-05-02 2022-08-21 美商科迪華農業科技有限責任公司 用於穀物中的真菌防治之協同性混合物
TWI774760B (zh) * 2017-05-02 2022-08-21 美商科迪華農業科技有限責任公司 用於蔬菜中的真菌防治之協同性混合物

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EP1380209A1 (fr) * 2001-04-17 2004-01-14 Nihon Nohyaku Co., Ltd. Composition d'agents pesticides et procede d'utilisation
EP1782689A1 (fr) * 2004-08-23 2007-05-09 Nihon Nohyaku Co., Ltd. Dérivé optiquement actif de phtalimide, insecticide pour l'agriculture ou l'horticulture et procédé d'utilisation de celui-ci
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EP2255640A2 (fr) 2006-12-22 2010-12-01 Bayer CropScience AG Composition pesticide comprenant du propamocarbe-fosétylate et une substance active insecticide
EP2245938A1 (fr) 2006-12-22 2010-11-03 Bayer CropScience AG Composition pesticide comprenant du fosétyl-aluminium et une substance active insecticide
WO2008077922A3 (fr) * 2006-12-22 2008-09-18 Bayer Cropscience Ag Composition pesticide contenant de la fénamidone et un composé insecticide
WO2008077925A1 (fr) * 2006-12-22 2008-07-03 Bayer Cropscience Ag Composition pesticide comprenant du propamocarbe-fosétylate et une substance active insecticide
EA022351B1 (ru) * 2006-12-22 2015-12-30 Байер Кропсайенс Аг Пестицидная композиция, содержащая пропамокарб-фосетилат и инсектицидно активное вещество
EP2258195A2 (fr) 2006-12-22 2010-12-08 Bayer CropScience AG Composition pesticide comprenant du propamocarbe-fosétylate et une substance active insecticide
EA022383B1 (ru) * 2006-12-22 2015-12-30 Байер Кропсайенс Аг Пестицидная композиция, содержащая пропамокарб-гидрохлорид и инсектицидно активное вещество
EP2258193A2 (fr) 2006-12-22 2010-12-08 Bayer CropScience AG Composition pesticide comprenant du propamocarbe-fosétylate et une substance active insecticide
EP2245937A1 (fr) 2006-12-22 2010-11-03 Bayer CropScience AG Composition pesticide comprenant du fosétyl-aluminium et une substance active insecticide
EP2250902A1 (fr) 2006-12-22 2010-11-17 Bayer CropScience AG Composition pesticide comprenant du fosétyl-aluminium et une substance active insecticide
EP2250900A1 (fr) 2006-12-22 2010-11-17 Bayer CropScience AG Composition pesticide comprenant du fosétyl-aluminium et une substance active insecticide
EP2250901A2 (fr) 2006-12-22 2010-11-17 Bayer CropScience AG Composition pesticide comprenant du fosétyl-aluminium et une substance active insecticide
EP2250899A2 (fr) 2006-12-22 2010-11-17 Bayer CropScience AG Composition pesticide comprenant du fosétyl-aluminium et une substance active insecticide
EP2250903A1 (fr) 2006-12-22 2010-11-17 Bayer CropScience AG Composition pesticide comprenant du fosétyl-aluminium et une substance active insecticide
EP2253209A2 (fr) 2006-12-22 2010-11-24 Bayer CropScience AG Composition pesticide comprenant du fosétyl-aluminium et une substance active insecticide
EP2255643A2 (fr) 2006-12-22 2010-12-01 Bayer CropScience Aktiengesellschaft Composition pesticide comprenant du propamocarbe-fosétylate et une substance active insecticide
EP2255642A2 (fr) 2006-12-22 2010-12-01 Bayer CropScience AG Composition pesticide comprenant du propamocarbe-fosétylate et une substance active insecticide
EP2255638A2 (fr) 2006-12-22 2010-12-01 Bayer CropScience AG Composition pesticide comprenant du propamocarbe-fosétylate et une substance active insecticide
EP2255641A2 (fr) 2006-12-22 2010-12-01 Bayer CropScience AG Composition pesticide comprenant du propamocarbe-fosétylate et une substance active insecticide
EP2255639A2 (fr) 2006-12-22 2010-12-01 Bayer CropScience AG Composition pesticide comprenant du propamocarbe-fosétylate et une substance active insecticide
WO2008077930A3 (fr) * 2006-12-22 2008-10-02 Bayer Cropscience Ag Composition pesticide comprenant du fosétyl-aluminium et une substance active insecticide
WO2008077930A2 (fr) * 2006-12-22 2008-07-03 Bayer Cropscience Ag Composition pesticide comprenant du fosétyl-aluminium et une substance active insecticide
US9161541B2 (en) 2006-12-22 2015-10-20 Bayer Intellectual Property Gmbh Pesticide composition comprising propamocarb-hydrochloride and an insecticide active substance
EP2255641A3 (fr) * 2006-12-22 2011-02-16 Bayer CropScience AG Composition pesticide comprenant du propamocarbe-fosétylate et une substance active insecticide
EA016313B1 (ru) * 2006-12-22 2012-04-30 Байер Кропсайенс Аг Пестицидная композиция, содержащая пропамокарбфосетилат и инсектицидно активное вещество
US8216971B2 (en) 2006-12-22 2012-07-10 Bayer Intellectual Property Gmbh Pesticide composition comprising propamocarb-hydrochloride and an insecticide active substance
US8236830B2 (en) 2006-12-22 2012-08-07 Bayer Cropscience Ag Pesticide composition comprising propamocarb-fosetylate and an insecticidally active substance
EA017006B1 (ru) * 2006-12-22 2012-09-28 Байер Кропсайенс Аг Пестицидная композиция, содержащая фенамидон и инсектицидное соединение
US8288426B2 (en) 2006-12-22 2012-10-16 Bayer Cropscience Ag Pesticidal composition comprising fenamidone and an insecticide compound
US8969392B2 (en) 2006-12-22 2015-03-03 Bayer Cropscience Ag Pesticide composition comprising propamocarb-fosetylate and an insecticidally active substance
US20100227900A1 (en) * 2009-02-03 2010-09-09 Bayer Cropscience Ag Use of Sulphur-Containing Heteroaromatic Acid Analogues as Bactericides
EP2239331A1 (fr) * 2009-04-07 2010-10-13 Bayer CropScience AG Procédé pour améliorer l'utilisation du potentiel de production dans des plantes transgéniques
CN101755795A (zh) * 2009-11-17 2010-06-30 陕西汤普森生物科技有限公司 一种含氟铃脲和氟虫双酰胺的增效杀虫组合物
CN103068236A (zh) * 2010-06-30 2013-04-24 拜耳知识产权有限责任公司 包含氟唑菌苯胺的协同活性成分结合物
CN103068236B (zh) * 2010-06-30 2015-07-15 拜耳知识产权有限责任公司 包含氟唑菌苯胺的协同活性成分结合物
JP2014530182A (ja) * 2011-09-16 2014-11-17 バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー 植物収量を向上させるためのアシルスルホンアミド類の使用
CN105307493A (zh) * 2013-03-05 2016-02-03 拜耳作物科学股份公司 酰基磺酰胺用于提高植物产量的用途
WO2014170354A1 (fr) * 2013-04-19 2014-10-23 Bayer Cropscience Ag Combinaisons synergiques insecticides et/ou fongicides de dérivés d'acide diamide phtalique et d'un autre ingrédient actif
US12114660B2 (en) 2014-12-30 2024-10-15 Corteva Agriscience Llc Picolinamide compounds with fungicidal activity
WO2021064252A1 (fr) 2019-10-05 2021-04-08 JEUNEN, Carlo Synergiste de pesticides sx-pyr
BE1027622A1 (fr) 2019-10-05 2021-04-28 Denis Mbonimpa Synergiste de pesticides sx-pyr

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AR059760A1 (es) 2008-04-30
TW200810691A (en) 2008-03-01
DE102006037120A1 (de) 2007-09-13
CL2007000571A1 (es) 2008-02-01

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