WO2014170354A1 - Insecticidal and/or fungicidal synergistic combinations of phthaldiamide derivatives and a further active ingredient - Google Patents

Insecticidal and/or fungicidal synergistic combinations of phthaldiamide derivatives and a further active ingredient Download PDF

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Publication number
WO2014170354A1
WO2014170354A1 PCT/EP2014/057687 EP2014057687W WO2014170354A1 WO 2014170354 A1 WO2014170354 A1 WO 2014170354A1 EP 2014057687 W EP2014057687 W EP 2014057687W WO 2014170354 A1 WO2014170354 A1 WO 2014170354A1
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methyl
group
alkyl
formula
phenyl
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PCT/EP2014/057687
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French (fr)
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Koen Van Den Eynde
Wolfgang Thielert
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Bayer Cropscience Ag
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Publication of WO2014170354A1 publication Critical patent/WO2014170354A1/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
    • A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/30—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N37/34—Nitriles

Definitions

  • the present invention relates to novel active compound combinations comprising firstly a known compound of the formula (I) and secondly at least one known fungicidally active compound, which novel active compound combinations are highly suitable for controlling unwanted animal pests such as insects and unwanted phytopathogenic fungi.
  • phthalic acid amides (Ryanodine receptor inhibitors class) have insecticidal activity (see, e.g., EP 0 919 542, W0 2004/018410 or W0 2010/012442). Cyano group containing phthalic acid amide-based compounds and their preparation are further disclosed in WO 2012/034472.
  • a first aspect refers to an active compound combination comprising at least one compound of the formula (I)
  • A represents individually halogen, cyano, nitro, hydroxyl, amino, Ci-Cs alkyl group, substituted Ci-Cs alkyl group having at least one substituent elected from the group consisting of halogen, hydroxy, cyano, nitro, amino, halo C1-C3 alkyl group, C1-C3 alkoxy group, halo C1-C3 alkoxy group, C1-C3 alkylthio group, halo C1-C3 alkylthio group, C1-C3 alkylsulfinyl group, halo C1-C3 alkylsulfinyl group, C1-C3 alkylsulfonyl group, halo C1-C3 alkylsulfonyl group and C1-C3 alkylthio, C1-C3 alkyl group; further, an arbitrary saturated carbon atom in said optionally substituted Ci-Cs alkyl group; n represents 0, 1 , 2,
  • P2 represents hydrogen, halogen, cyano Ci-Cs alkyl or Ci-Cs haloalkyl;
  • R3 represents O or S;
  • R represents O or S;
  • X represents a Ci-Cs alkyl group or a substituted Ci-Cs alkyl group having at least one substituent selected from the group consisting of halogen, hydroxy, cyano, nitro, amino, halo C1-C3 alkyl group, C1-C3 alkoxy group, halo C1-C3 alkoxy group; and at least one active compound selected from Groups (2) to (24) described herein.
  • One embodiment refers to said active compound combination wherein compound of formula (I) is compound (1-5).
  • Another aspect refers to the use of an active compound combination according to the invention for controlling animal pests.
  • Another aspect refers to a method for controlling animal pests, characterized in that an active compound combination according ot the invention is allowed to act on animal pests and/or their habitat and/or seed.
  • One embodiment refers to said method characterized in that an active compound of the formula I and one active compound selected from Groups (2) to (24) as described herein are allowed to act simultaneously on seed.
  • Another aspect refers to a process for preparing insecticidal and acaricidal compositions, characterized in that an active compound combination according to the invention is mixed with extenders and/or surfactants.
  • Another aspect refers to a seed treated with an active compound combination according to the invention.
  • Yet another aspect refers to a seed wherein a compound of formula (I) as described herein and a compound selected from compounds (II- 1), ( ⁇ -2), ( ⁇ -3), or (II-4) as described herein are present in one or different layers on the seed, a coating or as a further layer or further layers in addition to a coating.
  • Ri represents hydrogen, halogen, cyano Ci-Cs alkyl or Ci-Cs haloalkyl
  • R2 represents hydrogen, halogen, cyano Ci-Cs alkyl or Ci-Cs haloalkyl
  • R3 represents O or S
  • R represents O or S
  • X represents a Ci-Cs alkyl group or a substituted Ci-Cs alkyl group having at least one substituent selected from the group consisting of halogen, hydroxy, cyano, nitro, amino, halo C1-C3 alkyl group, C1-C3 alkoxy group, halo C1-C3 alkoxy group; and at least one active compound selected from Groups (2) to (24) below:
  • A represents NH or O
  • a 3 represents N or CH
  • L represents one of the groups
  • R 11 represents phenyl, phenoxy or pyridinyl, each of which is optionally mono- or disubstituted by identical or different substituents from the group consisting of chlorine, cyano, methyl and trifluoromethyl, or represents l-(4-chlorophenyl)pyrazol-3-yl or represents 1 ,2-propanedione-bis(0-methyloxime)- 1 -yl, R 12 represents hydrogen or fluorine;
  • R 13 represents hydrogen, fluorine, chlorine, phenyl or 4-chlorophenoxy
  • R 14 represents hydrogen or chlorine
  • a 5 represents C or Si (silicon)
  • R 15 represents hydrogen, hydroxyl or cyano
  • R 16 represents 1 -cyclopropylethyl, 1 -chlorocyclopropyl, Ci-C i-alkyl, Ci-Ce- hydroxyalkyl, Ci-C i-alkylcarbonyl, Ci-C2-haloalkoxy-Ci-C2-alkyl, trimethylsilyl-Ci-C2- alkyl, monofluorophenyl or phenyl,
  • R 15 and R 16 furthermore together represent -0-CH 2 -CH(R 18 )-0-, -0-CH 2 -CH(R 18 )-CH 2 -, or -0-CH-(2-chlorophenyl)-,
  • R 18 represents hydrogen, Ci-C i-alkyl or bromine;
  • X represents 2-chloro-3-pyridinyl, represents 1 -methylpyrazol-4-yl which is substituted in the 3-position by methyl or trifluoromethyl and in the 5-position by hydrogen or chlorine, represents 4-ethyl-2-ethylamino- l ,3-thiazol-5-yl, represents 1 - methylcyclohexyl, represents 2,2-dichloro-l -ethyl-3-methylcyclopropyl, represents 2- fluoro-2-propyl, 3,4-dichloroisothiazol-5-yl, 5,6-dihydro-2-methyl-l ,4-oxathiin-3-yl, 4- methyl-l ,2,3-thiadiazol-5-yl, 4,5-dimethyl-2-trimethylsilylthiophen-3-yl, 1 -methylpyrrol- 3-yl which is substituted in the 4-position by methyl or trifluoromethyl and in the 5-position by hydrogen or chlorine, or represents phen
  • Y represents a direct bond
  • Ci-C6-alkanediyl (alkyl) which is optionally substituted by chlorine, cyano or oxo
  • Z represents hydrogen, Ci-C6-alkyl or the group in which
  • a 6 represents CH or N
  • R 20 represents hydrogen, chlorine, cyano, Ci-Ce-alkyl, phenyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of chlorine and di(Ci-C3-alkyl)aminocarbonyl,
  • R 21 represents hydrogen, chlorine or isopropoxy
  • R 22 represents hydrogen, chlorine, hydroxyl, methyl, trifluoromethyl or di(G-C 3 - alkyl)aminocarbonyl,
  • R 20 and R 21 furthermore together represent *-CH(CH 3 )-CH 2 -C(CH 3 )2- or *-CH(CH 3 )-0-C(CH 3 ) 2 - where the bond marked with * is attached to R 20 ;
  • R 23 represents benzyl, furyl or methoxymethyl;
  • R 24 represents methyl, cyclopropyl or 1 -propynyl;
  • R 25 and R 26 each represent hydrogen or together represent -O-CF2-O-,
  • R 27 represents hydrogen, Ci-C4-alkylaminocarbonyl or represents dimethylisoxazol-4-ylsulphonyl,
  • R 28 represents chlorine, methoxycarbonylamino, chlorophenyl, furyl or thiazolyl;
  • Group (11) Carbamates of the general formula (IX) in which
  • R 29 represents n- or isopropyl
  • R 30 represents di(Ci-C2-alkyl)amino-C2-C4-alkyl or diethoxyphenyl, salts of these compounds also being included;
  • Group (12):Dicarboximides selected from
  • R 31 and R 32 independently of one another represent hydrogen or methyl
  • R 33 represents Ci-Cw-alkyl (preferably Ci2-Ci4-alkyl), Cs-Cn-cycloalkyl (preferably Cio-Ci2-cycloalkyl), phenyl-Ci-C4-alkyl, which may be substituted in the phenyl moiety by halogen or C i-C4-alkyl or represents acrylyl which is substituted by chlorophenyl and dimethoxyphenyl;
  • R 34 represents chlorine or cyano
  • R 35 represents chlorine or nitro
  • R 36 represents chlorine
  • R 3' and R 36 furthermore together represent -O-CF2-O-;
  • R 37 represents unsubstituted or fluorine-, chlorine-, bromine-, methyl- or ethyl- substituted phenyl, 2-naphthyl, 1 ,2,3,4-tetrahydronaphthyl or indanyl; l
  • a 7 represents a direct bond or -0-
  • R 38 represents hydrogen or Ci-C i-alkyl
  • R 39 represents Ci-C6-alkyl
  • R 40 represents Ci-C6-alkyl or C2-C6-alkenyl
  • R 41 represents Ci-C6-alkyl
  • R 40 and R 41 furthermore together represent C t-Cs-alkanediyl (alkyl) which is mono- or disubstituted by G-Ce-alkyl,
  • R 42 represents 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 represents hydrogen, fluorine or methyl
  • R 48 represents Ci-C6-alkyl
  • R 49 represents Ci-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl;
  • R 50 represents hydrogen or fluorine
  • R 52 represents hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl
  • Het represents one of the radicals Hetl to Het7 below:
  • R represents iodine, methyl, difluoromethyl or trifluoromethyl
  • R 54 represents hydrogen, fluorine, chlorine or methyl
  • R 55 represents methyl, difluoromethyl or trifluoromethyl
  • R 56 represents chlorine, bromine, iodine, methyl, difluoromethyl or trifluoromethyl
  • R 57 represents methyl or trifluoromethyl.
  • alkyl represents straight-chain or branched aliphatic hydrocarbons having 1 to 8, preferably 1 to 6, more preferably 1 to 3, carbon atoms. Suitable alkyl groups are, for example, methyl, ethyl, ⁇ -propyl, z ' -propyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl. The alkyl group may be unsubstituted or is substituted by at least one of the substituents mentioned here.
  • halogen or "Hal” represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine.
  • haloalkyl represents alkyl groups having up to 8 carbon atoms in which at least one hydrogen atom has been replaced by a halogen.
  • Suitable haloalkyl groups are, for example, CH 2 F, CHF 2 , CF 3 , CF 2 C1, CFC1 2 , CC1 3 , CF 2 Br, CF 2 CF 3 , CFHCF 3 , CH 2 CF 3 , CH 2 CH 2 F, CH 2 CHF 2 , CFC1CF 3 , CC1 2 CF 3 , CF 2 CH 3 , CF 2 CH 2 F, CF 2 CHF 2 , CF 2 CF 2 C1, CF 2 CF 2 Br, CFHCH 3 , CFHCHF 2 , CHFCF 3 , CHFCF 2 C1, CHFCF 2 Br, CFC1CF 3 , CC1 2 CF 3 , CF 2 CF 2 CF 3 , CH 2 CH 2 F, CH 2
  • the formula (III) embraces the following preferred mixing partners of group (3): (3-1) azaconazole (known from DE-A 25 51 560) of the formula
  • bromuconazole (known from EP-A 0 258 161) of the formula
  • the formula (IV) embraces the following preferred mixing partners of group (4): dichlofluanid (known from DE-A 11 93 498) of the formula
  • Preferred mixing partners of group (5) are newspaper ⁇
  • the formula (V) embraces the following preferred mixing partners of group (6): (6-1) 2-chloro-N-(l,l,3-trimethylindan-4-yl)nicotinamide (known from EP-A 0 256 503) of the formula
  • furametpyr (known from EP-A 0 315 502) of the formula
  • metiram (known from DE-A 10 76 434) having the IUPAC name zinc ammoniate ethylenebis(dithiocarbamate)-poly(ethylenethiuram disulphide) propineb (known from GB 935 981) of the formula
  • the formula (VI) embraces the following preferred mixing partners of group (8): (8-1) benalaxyl (known from DE-A 29 03 612) of the formula
  • furalaxyl (known from DE-A 25 13 732) of the formula
  • the formula (VII) embraces the following preferred mixing partners of group (9): (9-1) cyprodinil (known from EP-A 0 310 550) of the formula
  • the formula (IX) embraces the following preferred mixing partners of group (11): (11-1) diethofencarb (known from EP-A 0 078 663) of the formula
  • Preferred mixing partners of group (17) are (17-1) fosetyl-Al (known from DE-A 24 56 627) of the formula phosphonic acid (known chemical) of the formula
  • the formula (XII) embraces the following preferred mixing partners of group (18) which are known from WO 96/23793 and can in each case be present as E or Z isomers. Accordingly, compounds of the formula (XII) can 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 (XII) in the form of their E isomer: compound 2-(2,3-dihydro-lH-inden-5-yl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-
  • metrafenone (known from EP-A 0 897 904) of the formula
  • Preferred mixing partners of group (22) are (22-1) 5-chloro-N-[("7S)-2,2,2-trifluoro-l-methylethyl]-6-(2,4,6-trifluorophenyl)[l,2,4]triazolo- [l,5-a]pyrimidine-7-amine (known from US 5,986,135) of the formula
  • Preferred mixing partners of group (23) are (23-1) 2-butoxy-6-iodo-3-propylbenzopyran-4-one (known from WO 03/014103) of the formula
  • Compound (6-7), carpropamid, has three asymmetrically substituted carbon atoms. Accordingly, compound (6-7) can be present as a mixture of different isomers or else in the form of a single component. Particular preference is given to the compounds
  • Hal represents F, CI, I or Br
  • X' represents Ci-Ce alkyl or substituted Ci-Ce alkyl having at least one substituent selected from the group consisting of halogen, hydroxy, cyano, nitro, amino, halo C1-C3 alkyl group, preferably a Ci-C6cyanoalkyl;
  • A' represents C1-C3 alkyl, C1-C3 haloalkyl, halogen, preferably methyl, halomethyl, ethyl or haloethyl, more preferably methyl or ethyl;
  • n represents 0, 1, 2, 3 or 4, preferably 0, 1 or 2, more preferably 1.
  • a composition comprises at least one compound of the general formula (I) selected from the group consisting of compound (1-2), (1-3), (1-4) or (1-5):
  • a compound of formula (I) is selected from the group consisting of compound (1-2) or compound (1-5).
  • the compound of formula (I) is compound (1-5).
  • Particularly preferred active compounds of groups (2) to (24) are the following active compounds:
  • active compounds of the groups (2) to (24) are the following active compounds: (2-2) fluoxastrobin
  • Especially preferred mixing partners are the following active compounds:
  • Active compound of group I Active compound of groups 2 to 24
  • Embodiments of the invention which are emphasized for the treatment of seed are mixtures comprising a compound selected from the group (I) consisting of compound (1-2), (1-3), (1 -4) and (1-5) and a compound selected from the group consisting of fluoxastrobin (2-2) and/or trifloxystrobin (2-4) and/or prothioconazole (3-15) and/or tebuconazole (3-17) and/or ipconazole (3-18) and/or triticonazole (3-20) and/or triadimenol (3-22) and/or carpropamid (6-7) and/or N-[2- ( 1 ,3 -dimethylbutyl)phenyl] -5 -fluoro- 1 ,3 -dimethyl- 1 H-pyrazole-4-carboxamide (6-18) and/ or thiram (7-5) and/or metalaxyl (8-3) and/or metalaxyl-M (8-4) and/or N-( ⁇ 4-
  • Embodiments of the invention which are emphasized for the treatment of seed are furthermore mixtures comprising a compound selected from the group (I) consisting of compound (1-2), (1-3), (1-4) and (1-5) and a compound selected from the group consisting of fluoxastrobin (2- 2) and/or trifloxystrobin (2-4) and/or prothioconazole (3-15) and/or tebuconazole (3-17) and/or ipconazole (3-18) and/or triticonazole (3-20) and/or triadimenol (3-22) and/or carpropamid (6-7) and/or N-[2-(l,3-dimethylbutyl)phenyl]-5-fluoro-l,3-dimethyl-lH-pyrazole-4-carboxamide (6-18) and/or thiram (7-5) and/or metalaxyl (8-3) and/or metalaxyl-M (8-4) and/or N-( ⁇ 4- [(cyclopropyl)
  • the active compound combinations according to the invention comprise at least one active compound from the compounds of groups (2) to (24). In addition, they may also comprise further fungicidally active additives.
  • the synergistic effect is particularly pronounced when the active compounds in the active compound combinations according to the invention are present in certain weight ratios.
  • the weight ratios of the active compounds in the active compound combinations can be varied within a relatively wide range.
  • the combinations according to the invention comprise an active compound of the formula (I) and one of the active compounds of group (2) to (24) in the following preferred and particularly preferred mixing ratios:
  • More preferred mixing ratio 40: 1 to 1 :40
  • mixing ratios are, e.g. 20: 1 to 1 :20, 15: 1 to 1 : 15, 10: 1 to 1 : 10, 5: 1 to 1 :5, 3: 1 to 1 :3, 2: 1 to 1 :2 or combinations thereof such as 20:1 to 1 :5 or 5: 1 to 1 :3.
  • a combination according to the invention is characterized in that compound (I) is compound (1-5) and an active compound of group (2) to (24) is selected from the group consisting of Metalaxyl (8-3), Cyproconazole (3-6), Fludioxonil (16-2), and Propamocarb-hydrochloride (11-3).
  • preferred mixing ratios for a combination of compound (1-5) and Metalaxyl (8-3) are 2: 1 to 1 : 100, more preferably 1 : 1 to 1 : 100.
  • preferred mixing ratios for a combination of compound (1-5) and Cyproconazole (3-6) are 1 : 1 to 1 :15, more preferably 1 :4 to 1 : 12.
  • Further preferred mixing ratios for a combination of compound (1-5) and Fludioxonil (16- 2) are 2: 1 to 1 :200, more preferably 1,25:1 to 1 :170.
  • Further preferred mixing ratios for a combination of compound (1-5) and Propamocarb- hydrochloride (11-3) are 1 : 1 to 1 :200, more preferably 4: 1 to 1 :170.
  • the mixing ratios are based on weight ratios. The ratio is to be understood as meaning active compound of the formula (I) : active compound of any one of groups (2) to (24).
  • the active compound combinations according to the invention in combination with good plant tolerance and favourable toxicity to warm-blooded animals and being tolerated well by the environment, are suitable for protecting plants and plant organs, for increasing the harvest yields, for improving the quality of the harvested material and for controlling animal pests, in particular insects, arachnids, helminths, nematodes and molluscs, which are encountered in agriculture, in horticulture, in animal husbandry, in forests, in gardens and leisure facilities, in the protection of stored products and of materials, and in the hygiene sector. They may be preferably employed as plant protection agents. They are active against normally sensitive and resistant species and against all or some stages of development.
  • pests include pests: from the order of the Anoplura (Phthiraptera), from the class of the Arachnida, from the class of the Bivalva, from the order of the Chilopoda, from the order of the Coleoptera, from the order of the Collembola, from the order of the Dermaptera, from the order of the Diplopoda, from the order of the Diptera, from the class of the Gastropoda, from the class of the helminths, it is furthermore possible to control protozoa, from the order of the Heteroptera, from the order of the Homoptera, from the order of the Hymenoptera, from the order of the Isopoda, from the order of the Isoptera, from the order of the Lepidoptera, from the order of the Orthoptera, from the order of the Siphonaptera, from the order of the Symphyla, from the order of the Thysanoptera, from the order of the Thysan
  • the active compound combinations according to the invention can, at certain concentrations or application rates, also be used as herbicides, safeners, growth regulators or agents to improve plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including agents against viroids) or as agents against MLO (Mycoplasma- like organisms) and RLO (Rickettsia- like organisms). If appropriate, they can also be employed as intermediates or precursors for the synthesis of other active compounds.
  • plants and plant parts can be treated in accordance with the invention.
  • Plants are to be understood as meaning in the present context 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 plant breeding and optimization methods or by rn
  • Plant parts are to be understood as meaning all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, stems, flowers, fruit bodies, fruits and seeds and also roots, tubers and rhizomes.
  • the plant parts also include harvested material, and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • Treatment according to the invention of the plants and plant parts with the active compound combinations is carried out directly or by allowing the compounds to act on the surroundings, habitat or storage space by the customary treatment methods, for example by immersion, spraying, evaporation, fogging, scattering, painting on, injection and, in the case of propagation material, in particular in the case of seeds, also by applying one or more coats.
  • the active compound combinations according to the invention are particularly suitable for treating seed.
  • the combinations according to the invention mentioned above as preferred or particularly preferred may be mentioned as being preferred.
  • This phase is particularly critical since the roots and shoots of the growing plant are particularly sensitive and even minor damage can lead to the death of the whole plant. Protecting the seed and the germinating plant by the use of suitable compositions is therefore of particularly great interest.
  • the present invention relates in particular also to a method for protecting seed and germinating plants against attack by pests which comprises treating the seed with an active compound combination according to the invention.
  • the method according to the invention for friendship comprises joining the seed with an active compound combination according to the invention.
  • - 61 - protecting seed and germinating plants against attack by pests comprises a method wherein the seed is treated simultaneously with an active compound of the formula I and one of the active compounds of group (2) to (24).
  • the invention also comprises a method wherein the seed is treated at different times with an active compound of the formula I and one of the active compounds of group (2) to (24).
  • the invention also relates to the use of the active compound combinations according to the invention for treating seed for protecting the seed and the plant emerging therefrom against pests.
  • the invention relates to seed treated with an active compound combination according to the invention for protection against pests.
  • the invention also relates to seed treated simultaneously with an active compound of the formula I and one of the active compounds of group (2) to (24).
  • the invention furthermore relates to seed treated at different times with an active compound of the formula I and one of the active compounds of group (2) to (24).
  • the individual active compounds of the composition according to the invention may be present in different layers on the seed.
  • the layers comprising an active compound of the formula I and one of the active compounds of group (2) to (24) may optionally be separated by an intermediate layer.
  • the invention also relates to seed where an active compound of the formula I and one of the active compounds of group (2) to (24) are applied as component of a coating or as a further layer or further layers in addition to a coating.
  • One of the advantages of the present invention is that the particular systemic properties of the active compound combinations according to the invention mean that treatment of the seed with these active compound combinations not only protects the seed itself, but also the resulting plants after emergence, from pests. In this manner, the immediate treatment of the crop at the time of sowing or shortly thereafter can be dispensed with.
  • a further advantage is the synergistically increased insecticidal activity of the active compound combinations according to the invention in comparison with the insecticidal individual active compound, which exceeds the expected activity of the two active compounds when applied individually. Also advantageous is the synergistically increased fungicidal activity of the active compound combinations according to the invention in comparison with the fungicidal individual active compound, which exceeds the expected activity of the active compound when applied individually. This makes possible an optimization of the amount of active compounds employed.
  • the active compound combinations according to the invention can be employed also in particular in transgenic seed, the plants arising from this seed being capable of expressing a protein directed against pests.
  • certain pests can be controlled merely by the expression of the, for example, insecticidal protein, and additionally be protected by the active compound combinations according to the invention against damage.
  • the active compound combinations according to the invention are suitable for protecting seed of any plant variety as already mentioned above which is employed in agriculture, in the greenhouse, in forests or in horticulture.
  • this takes the form of seed of maize, peanut, canola, oilseed rape, poppy, soya beans, cotton, beet (for example sugar beet and fodder beet), rice, sorghum and millet, wheat, barley, oats, rye, sunflower, tobacco, potatoes or vegetables (for example tomatoes, cabbage plants).
  • the active compound combinations according to the invention are likewise suitable for treating the seed of fruit plants and vegetables as already mentioned above.
  • transgenic seed with an active compound combination according to the invention is also of particular importance.
  • the heterologous genes in transgenic seed may be derived from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly suitable for the treatment of transgenic seed which comprises at least one heterologous gene originating from Bacillus sp. and whose gene product shows activity against the European corn borer and/or the corn root worm. It is particularly preferably a heterologous gene derived from Bacillus thuringiensis .
  • the active compound combination according to the invention is applied to the seed either alone or in a suitable formulation.
  • the seed is treated in a state which is stable enough to avoid damage during treatment.
  • the seed may be treated at any point in time between harvest and sowing.
  • the seed usually used has been separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits.
  • the active compound combinations can be converted to the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, granules for broadcasting, suspension-emulsion concentrates, natural materials impregnated with active compound, synthetic materials impregnated with active compound, fertilizers and microencapsulations in polymeric substances.
  • customary formulations such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, granules for broadcasting, suspension-emulsion concentrates, natural materials impregnated with active compound, synthetic materials impregnated with active compound, fertilizers and microencapsulations in polymeric substances.
  • These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants and/or foam-formers.
  • extenders that is liquid solvents and/or solid carriers
  • surfactants that is emulsifiers and/or dispersants and/or foam-formers.
  • the formulations are prepared either in suitable plants or else before or during the application.
  • auxiliaries are substances which are suitable for imparting to the composition itself and/or to preparations derived therefrom (for example spray liquors, seed dressings) particular properties such as certain technical properties and/or also particular biological properties.
  • suitable auxiliaries are: extenders, solvents and carriers.
  • Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, for example from the classes of the aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, if appropriate, may also be substituted, etherified and/or esterified), the ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly)ethers, the unsubstituted and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulphones and sulphoxides (such as dimethyl sulphoxide).
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • the alcohols and polyols
  • suitable liquid solvents are: 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, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and also their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl sulphoxide, and also water.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclo
  • 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 ground synthetic minerals, such as finely divided silica, alumina and silicates;
  • suitable solid carriers for granules are: for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic meals, and granules of organic material such as paper, sawdust, coconut shells, maize cobs and tobacco stalks;
  • suitable emulsifiers and/or foam-formers are: for example, nonionic and anionic emulsifiers, such as polyoxy ethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates,
  • oligo- or polymers for example those derived from vinylic monomers, from acrylic acid, from EO and/or PO alone or in combination with, for example, (poly)alcohols or (poly)amines. It is also possible to employ lignin and its sulphonic acid derivatives, unmodified and modified celluloses, aromatic and/or aliphatic sulphonic acids and their adducts with formaldehyde.
  • Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations.
  • colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs
  • trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • perfumes mineral or vegetable, optionally modified oils, waxes and nutrients (including trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Stabilizers such as low-temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve chemical and/or physical stability may also be present.
  • the formulations generally comprise between 0.01 and 98% by weight of active compound, preferably between 0.5 and 90%.
  • the active compound combinations according to the invention in commercially available formulations and in the use forms prepared from these formulations, can be present in a mixture with other active compounds such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators or herbicides.
  • active compounds such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators or herbicides.
  • the insecticides include, for example, phosphoric esters, carbamates, carboxylic esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, and the like.
  • the active compound combinations according to the invention can furthermore be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with synergistic agents.
  • Synergistic agents are compounds which increase the action of the active compounds, without it being necessary for the synergistic agent added to be active itself.
  • the active compound content of the use forms prepared from the commercially available formulations can vary within wide limits.
  • the active compound concentration of the use forms can be from 0.00000001 to 95% by weight of active compound, preferably between 0.00001 and 1% by weight.
  • plants of the plant cultivars which are in each case commercially available or in use are treated according to the invention.
  • Plant cultivars are to be understood as meaning plants having novel properties ("traits") which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, bio- or genotypes.
  • the treatment according to the invention may also result in superadditive (“synergistic") effects.
  • superadditive for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity 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 drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products are possible, which exceed the effects which were actually to be expected.
  • the plants listed can be treated in a particularly advantageous manner with the active compound combinations according to the invention.
  • the preferred ranges stated above for the active compound combinations also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the active compound combinations specifically mentioned in the present text. - 66 -
  • the active compound combinations according to the invention act not only against plant, hygiene and stored product pests, but also in the veterinary medicine sector against animal parasites (ecto- and endoparasites), such as hard ticks, soft ticks, mange mites, leaf mites, flies (biting and licking), parasitic fly larvae, lice, hair lice, feather lice and fleas.
  • animal parasites ecto- and endoparasites
  • ecto- and endoparasites such as hard ticks, soft ticks, mange mites, leaf mites, flies (biting and licking), parasitic fly larvae, lice, hair lice, feather lice and fleas.
  • These parasites include: [0095] From the order of the Anoplurida, from the order of the Mallophagida and the suborders Amblycerina and Ischnocerina, from the order of the Diptera and the suborders Nematocerina and Brachycerina, from the order of the Siphonaptrida, from the order of the Heteropterida, from the order of the Blattarida, from the subclass of the Acari (Acarina) and the orders of the Meta- and Mesostigmata, from the order of the Actinedida (Prostigmata) and Acaridida (Astigmata).
  • the active compound combinations according to the invention are also suitable for controlling arthropods which infest agricultural productive livestock, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese and bees, other pets, such as, for example, dogs, cats, caged birds and aquarium fish, and also so-called test animals, such as, for example, hamsters, guinea pigs, rats and mice.
  • arthropods cases of death and reduction in productivity (for meat, milk, wool, hides, eggs, honey etc.) should be diminished, so that more economic and easier animal husbandry is possible by use of the active compound combinations according to the invention.
  • the active compound combinations according to the invention are used in the veterinary sector and in animal husbandry in a known manner by enteral administration in the form of, for example, tablets, capsules, potions, drenches, granules, pastes, boluses, the feed-through process and suppositories, by parenteral administration, such as, for example, by injection (intramuscular, subcutaneous, intravenous, intraperitoneal and the like), implants, by nasal administration, by dermal use in the form, for example, of dipping or bathing, spraying, pouring on and spotting on, washing and powdering, and also with the aid of moulded articles containing the active compounds, such as collars, ear marks, tail marks, limb bands, halters, marking devices and the like.
  • enteral administration in the form of, for example, tablets, capsules, potions, drenches, granules, pastes, boluses, the feed-through process and suppositories
  • parenteral administration such
  • the active compound combinations can be used as formulations (for example powders, emulsions, free-flowing compositions), which comprise the active compounds in an amount of 1 to 80% by weight, directly or after 100 to 10 000-fold dilution, or they can be used as a chemical bath.
  • formulations for example powders, emulsions, free-flowing compositions
  • the active compounds in an amount of 1 to 80% by weight, directly or after 100 to 10 000-fold dilution, or they can be used as a chemical bath.
  • insects may be mentioned as examples and as preferred - but without any limitation: Beetles, Hymenopterons, Termites, Bristletails.
  • Industrial materials in the present connection are to be understood as meaning non-living materials, such as, preferably, plastics, adhesives, sizes, papers and cardboards, leather, wood and processed wood products and coating compositions.
  • the ready-to-use compositions may, if appropriate, comprise further insecticides and, if appropriate, one or more fungicides.
  • the active compound combinations according to the invention can likewise be employed for protecting objects which come into contact with seawater or brackish water, in particular hulls, screens, nets, buildings, moorings and signalling systems, against fouling.
  • active compound combinations according to the invention may be employed as antifouling agents.
  • the active compound combinations are also suitable for controlling animal pests, in particular insects, arachnids and mites, which are found in enclosed spaces such as, for example, dwellings, factory halls, offices, vehicle cabins and the like. They can be employed alone or in combination with other active compounds and auxiliaries in domestic insecticide products for controlling these pests. They are active against sensitive and resistant species and against all developmental stages. These pests include:
  • a synergistic effect in insecticides and acaricides is always present when the activity of the active compound combinations exceeds the total of the activities of the active compounds when applied individually.
  • X is the kill rate, expressed in % of the untreated control, when active compound A is applied at an application rate of m g/ha or at a concentration of m ppm,
  • Y is the kill rate, expressed in % of the untreated control, when active compound B is applied at an application rate of n g/ha or at a concentration of n ppm and
  • E is the kill rate, expressed in % of the untreated control, when active compounds A and B is applied at application rates of m and n g/ha or at a concentration of m and n ppm, then
  • the actual kill rate is greater than calculated, the kill of the combination is superadditive, i.e. there is a synergistic effect.
  • the actual observed kill rate has to be greater than the value for the expected kill rate (E) calculated from the formula given above.
  • Emulsifier 0.5 parts by weight alkylarylpolyglycolether
  • Maize (Zea perennial insect) leaf sections are sprayed with a preparation of the active ingredient of the desired concentration. Once dry, the leaf sections are infested with fall armyworm larvae (Spodoptera frugiperda).
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and is diluted with water, containing an emulgator concentration of 1 OOOppm, to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water. Ammonium salt and/or penetration enhancer in a dosage of 1 OOOppm are added to the desired concentration if necessary.
  • Cabbage leaves (Brassica oleraced) are treated by being sprayed with the preparation of the active compound of the desired concentration and are infested with mustard beetle larvae ⁇ Phaedon cochleariae).

Abstract

The present invention relates to novel active compound combinations comprising at least one known compound of the formula (I) in which X, R1 to R4, A, n, Y, and m are as defined in the description, and at least one compound selected from the active compound groups (2) to (24) listed in the description have very good insecticidal and fungicidal properties.

Description

INSECTICIDAL AND/OR FUNGICIDAL SYNERGISTIC COMBINATIONS OF PHTHALDIAMIDE DERIVATIVES AND A FURTHER ACTIVE INGREDIENT
[0001] The present invention relates to novel active compound combinations comprising firstly a known compound of the formula (I) and secondly at least one known fungicidally active compound, which novel active compound combinations are highly suitable for controlling unwanted animal pests such as insects and unwanted phytopathogenic fungi.
Background
[0002] It is known that phthalic acid amides (Ryanodine receptor inhibitors class) have insecticidal activity (see, e.g., EP 0 919 542, W0 2004/018410 or W0 2010/012442). Cyano group containing phthalic acid amide-based compounds and their preparation are further disclosed in WO 2012/034472.
Summary
[0003] A first aspect refers to an active compound combination comprising at least one compound of the formula (I)
Figure imgf000002_0001
wherein
A represents individually halogen, cyano, nitro, hydroxyl, amino, Ci-Cs alkyl group, substituted Ci-Cs alkyl group having at least one substituent elected from the group consisting of halogen, hydroxy, cyano, nitro, amino, halo C1-C3 alkyl group, C1-C3 alkoxy group, halo C1-C3 alkoxy group, C1-C3 alkylthio group, halo C1-C3 alkylthio group, C1-C3 alkylsulfinyl group, halo C1-C3 alkylsulfinyl group, C1-C3 alkylsulfonyl group, halo C1-C3 alkylsulfonyl group and C1-C3 alkylthio, C1-C3 alkyl group; further, an arbitrary saturated carbon atom in said optionally substituted Ci-Cs alkyl group; n represents 0, 1 , 2, 3 or 4, preferably 0, 1 or 2; represents hydrogen, halogen, cyano Ci-Cs alkyl or Ci-Cs haloalkyl;
P2 represents hydrogen, halogen, cyano Ci-Cs alkyl or Ci-Cs haloalkyl; R3 represents O or S; R represents O or S;
Y represents individually hydrogen, halogen, cyano, nitro, Ci-Ce alkyl group, halo Ci-Ce alkyl group, C2-C6 alkenyl group, halo C2-C6 alkenyl group, C2-C6 alkynyl group, halo C2-C6 alkynyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, Ci-Ce alkoxy group, halo Ci- e alkoxy group, Ci-Ce alkylthio group, halo Ci-Ce alkylthio group, Ci-Ce alkylsulfinyl group, halo Ci-Ce alkylsulfinyl group, Ci-Ce alkylsulfonyl group, or halo Ci-Ce alkylsulfonyl group; m represents 0, 1 , 2, 3, or 4;
X represents a Ci-Cs alkyl group or a substituted Ci-Cs alkyl group having at least one substituent selected from the group consisting of halogen, hydroxy, cyano, nitro, amino, halo C1-C3 alkyl group, C1-C3 alkoxy group, halo C1-C3 alkoxy group; and at least one active compound selected from Groups (2) to (24) described herein.
One embodiment refers to said active compound combination wherein compound of formula (I) is compound (1-5). [0004] Another aspect refers to the use of an active compound combination according to the invention for controlling animal pests.
[0005] Another aspect refers to a method for controlling animal pests, characterized in that an active compound combination according ot the invention is allowed to act on animal pests and/or their habitat and/or seed. [0006] One embodiment refers to said method characterized in that an active compound of the formula I and one active compound selected from Groups (2) to (24) as described herein are allowed to act simultaneously on seed.
[0007] Another aspect refers to a process for preparing insecticidal and acaricidal compositions, characterized in that an active compound combination according to the invention is mixed with extenders and/or surfactants.
[0008] Further aspects refer to the use of an active compound combination according to the invention for treating seed or for treating transgenic plants or, more specifically, for treating seed of transgenic plants.
[0009] Another aspect refers to a seed treated with an active compound combination according to the invention. [0010] Yet another aspect refers to a seed wherein a compound of formula (I) as described herein and a compound selected from compounds (II- 1), (Π-2), (Π-3), or (II-4) as described herein are present in one or different layers on the seed, a coating or as a further layer or further layers in addition to a coating. Detailed description
[001 1 ] It has now been found that active compound combinations of at least one compound of the formula (I)
Figure imgf000004_0001
wherein A represents individually halogen, cyano, nitro, hydroxyl, amino, Ci-Cs alkyl group, substituted Ci-Cs alkyl group having at least one substituent elected from the group consisting of halogen, hydroxy, cyano, nitro, amino, halo C1-C3 alkyl group, C1-C3 alkoxy group, halo C1-C3 alkoxy group, C1-C3 alkylthio group, halo C1-C3 alkylthio group, C1-C3 alkylsulfinyl group, halo C1-C3 alkylsulfinyl group, C1-C3 alkylsulfonyl group, halo C1-C3 alkylsulfonyl group and C1-C3 alkylthio, C1-C3 alkyl group; further, an arbitrary saturated carbon atom in said optionally substituted Ci-Cs alkyl group; n represents 0, 1 , 2, 3 or 4, preferably 0, 1 or 2;
Ri represents hydrogen, halogen, cyano Ci-Cs alkyl or Ci-Cs haloalkyl; R2 represents hydrogen, halogen, cyano Ci-Cs alkyl or Ci-Cs haloalkyl; R3 represents O or S; R represents O or S;
Y represents individually hydrogen, halogen, cyano, nitro, Ci-Ce alkyl group, halo Ci-Ce alkyl group, C2-C6 alkenyl group, halo C2-C6 alkenyl group, C2-C6 alkynyl group, halo C2-C6 alkynyl group, C3-C6 cycloalkyl group, halo C3-C6 cycloalkyl group, Ci-Ce alkoxy group, halo Ci- e alkoxy group, Ci-Ce alkylthio group, halo Ci-Ce alkylthio group, Ci-Ce alkylsulfinyl group, halo Ci-Ce alkylsulfinyl group, Ci-Ce alkylsulfonyl group, or halo Ci-Ce alkylsulfonyl group; m represents 0, 1 , 2, 3, or 4;
X represents a Ci-Cs alkyl group or a substituted Ci-Cs alkyl group having at least one substituent selected from the group consisting of halogen, hydroxy, cyano, nitro, amino, halo C1-C3 alkyl group, C1-C3 alkoxy group, halo C1-C3 alkoxy group; and at least one active compound selected from Groups (2) to (24) below:
Group (2) Strobilurins of the general formula (II)
Figure imgf000005_0001
A represents NH or O, A3 represents N or CH, L represents one of the groups
Figure imgf000005_0002
where the bond marked with an asterisk (*) is attached to the phenyl ring,
R11 represents phenyl, phenoxy or pyridinyl, each of which is optionally mono- or disubstituted by identical or different substituents from the group consisting of chlorine, cyano, methyl and trifluoromethyl, or represents l-(4-chlorophenyl)pyrazol-3-yl or represents 1 ,2-propanedione-bis(0-methyloxime)- 1 -yl, R12 represents hydrogen or fluorine; Group (3) Triazoles of the general formula (III)
Figure imgf000006_0001
in which represents hydrogen or SH, represents 0 or 1 ,
R13 represents hydrogen, fluorine, chlorine, phenyl or 4-chlorophenoxy, R14 represents hydrogen or chlorine,
A represents a direct bond, -CH2-, -(0¾)2-, -0-, represents *-CH2-CHR17- or *- CH=CR17-, where the bond marked with * is attached to the phenyl ring, in which case R15 and R17 together represent -CH2-CH2-CH[CH(CH3)2]- or -CH2-CH2-C(CH3)2-,
A5 represents C or Si (silicon),
A4 further represents -N(R17)- and A5 furthermore together with R15 and R16 represents the group C=N-R18, in which case R17 and R18 together represent the group
Figure imgf000006_0002
, where the bond marked with * is attached to R17, R15 represents hydrogen, hydroxyl or cyano,
R16 represents 1 -cyclopropylethyl, 1 -chlorocyclopropyl, Ci-C i-alkyl, Ci-Ce- hydroxyalkyl, Ci-C i-alkylcarbonyl, Ci-C2-haloalkoxy-Ci-C2-alkyl, trimethylsilyl-Ci-C2- alkyl, monofluorophenyl or phenyl,
R15 and R16 furthermore together represent -0-CH2-CH(R18)-0-, -0-CH2-CH(R18)-CH2-, or -0-CH-(2-chlorophenyl)-,
R18 represents hydrogen, Ci-C i-alkyl or bromine; Group (4) Sulphenamides of the general formula (IV)
Figure imgf000007_0001
in which R represents hydrogen or methyl; Group (5) Valinamides selected from (5-1) iprovalicarb
(5-2) N1-[2-(4- {[3-(4-chlorophenyl)-2-propynyl]oxy} -3-methoxyphenyl)ethyl]-N2 (methylsulphonyl)-D-valinamide
(5-3) benthiavalicarb
Group (6) Carboxamides of the general formula (V)
Figure imgf000007_0002
in which
X represents 2-chloro-3-pyridinyl, represents 1 -methylpyrazol-4-yl which is substituted in the 3-position by methyl or trifluoromethyl and in the 5-position by hydrogen or chlorine, represents 4-ethyl-2-ethylamino- l ,3-thiazol-5-yl, represents 1 - methylcyclohexyl, represents 2,2-dichloro-l -ethyl-3-methylcyclopropyl, represents 2- fluoro-2-propyl, 3,4-dichloroisothiazol-5-yl, 5,6-dihydro-2-methyl-l ,4-oxathiin-3-yl, 4- methyl-l ,2,3-thiadiazol-5-yl, 4,5-dimethyl-2-trimethylsilylthiophen-3-yl, 1 -methylpyrrol- 3-yl which is substituted in the 4-position by methyl or trifluoromethyl and in the 5-position by hydrogen or chlorine, or represents phenyl which is mono- to trisubstituted by identical or different substituents from the group consisting of chlorine, methyl and trifluoromethyl,
Y represents a direct bond, Ci-C6-alkanediyl (alkyl) which is optionally substituted by chlorine, cyano or oxo, represents C2-C6-alkenediyl (alkenylene) or thiophenediyl,
Z represents hydrogen, Ci-C6-alkyl or the group in which
Figure imgf000008_0001
A6 represents CH or N,
R20 represents hydrogen, chlorine, cyano, Ci-Ce-alkyl, phenyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of chlorine and di(Ci-C3-alkyl)aminocarbonyl,
R21 represents hydrogen, chlorine or isopropoxy,
R22 represents hydrogen, chlorine, hydroxyl, methyl, trifluoromethyl or di(G-C3- alkyl)aminocarbonyl,
R20 and R21 furthermore together represent *-CH(CH3)-CH2-C(CH3)2- or *-CH(CH3)-0-C(CH3)2- where the bond marked with * is attached to R20;
Group (7) Dithiocarbamates selected from
(7-1 mancozeb
(7-2 maneb
(7-3 metiram
(7-4 propineb
(7-5 thiram
(7-6 zineb
(7-7) ziram
Group (8) Acylalanines of the general formula (VI)
Figure imgf000008_0002
in which * marks a carbon atom in the R or the S configuration, preferably in the S configuration,
R23 represents benzyl, furyl or methoxymethyl; Group (9): Anilinopyrimidines of the general formula (VII)
Figure imgf000009_0001
in which
R24 represents methyl, cyclopropyl or 1 -propynyl; Group (10):Benzimidazoles of the general formula (VIII)
Figure imgf000009_0002
in which
R25 and R26 each represent hydrogen or together represent -O-CF2-O-,
R27 represents hydrogen, Ci-C4-alkylaminocarbonyl or represents dimethylisoxazol-4-ylsulphonyl,
R28 represents chlorine, methoxycarbonylamino, chlorophenyl, furyl or thiazolyl; Group (11): Carbamates of the general formula (IX)
Figure imgf000009_0003
in which
R29 represents n- or isopropyl,
R30 represents di(Ci-C2-alkyl)amino-C2-C4-alkyl or diethoxyphenyl, salts of these compounds also being included; Group (12):Dicarboximides selected from
(12-1) captafol
(12-2) captan
(12-3) folpet
(12-4) iprodione
(12-5) procymidone
(12-6) vinclozolin
Group (13):Guanidines selected from
(13-1) dodine
(13-2) guazatine
(13-3) iminoctadine triacetate
(13-4) iminoctadine tris(albesilate)
Group (14): Imidazoles selected from
(14-1) cyazofamid
(14-2) prochloraz
(14-3) triazoxide
(14-4) pefurazoate
Group (15):Morpholines of the general formula (X)
Figure imgf000010_0001
in which R31 and R32 independently of one another represent hydrogen or methyl,
R33 represents Ci-Cw-alkyl (preferably Ci2-Ci4-alkyl), Cs-Cn-cycloalkyl (preferably Cio-Ci2-cycloalkyl), phenyl-Ci-C4-alkyl, which may be substituted in the phenyl moiety by halogen or C i-C4-alkyl or represents acrylyl which is substituted by chlorophenyl and dimethoxyphenyl;
Group (16): Pyrroles of the general formula (XI)
Figure imgf000011_0001
in which
R34 represents chlorine or cyano, R35 represents chlorine or nitro, R36 represents chlorine,
R3' and R36 furthermore together represent -O-CF2-O-; Group (17):(Thio)phosphonates selected from (17-1) fosetyl-Al, (17-2) phosphonic acid, (17-3) tolclophos-methyl; Group (18):Phenylethanamides of the general formula (XII)
Figure imgf000011_0002
in which
R37 represents unsubstituted or fluorine-, chlorine-, bromine-, methyl- or ethyl- substituted phenyl, 2-naphthyl, 1 ,2,3,4-tetrahydronaphthyl or indanyl; l
Group (19): Fungicides selected from
(19-1) acibenzolar-S-methyl
(19-2) chlorothalonil
(19-3) cymoxanil
(19-4) edifenphos
(19-5) famoxadone
(19-6) fluazinam
(19-7) copper oxychloride
(19-8) copper hydroxide
(19-9) oxadixyl
(19-10) spiroxamine
(19-11) dithianon
(19-12) metrafenone
(19-14) 2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one (19-15) probenazole
(19-16) isoprothiolane
(19-17) kasugamycin
(19-18) phthalide
(19-19) ferimzone
(19-20) tricyclazole
(19-21) cyprosulfamide
(19-22) mandipropamid
(19-23) quinoxyfen (known from EP-A 326 330) of the formula „
- 12 -
Figure imgf000013_0001
(19-24) proquinazid (known from WO 94/26722) of the formula
Figure imgf000013_0002
Group (20): (Thio)urea derivatives selected from
(20-1) pencycuron
(20-2) thiophanate-methyl
(20-3) thiophanate- ethyl
Group (21): Amides of the general formula (XIII)
Figure imgf000013_0003
in which
A7 represents a direct bond or -0-,
A8 represents -C(=0)NH- or -NHC(=0)-,
R38 represents hydrogen or Ci-C i-alkyl,
R39 represents Ci-C6-alkyl;
Group (22):Triazolopyrimidines of the general formula (XIV) ,„
Figure imgf000014_0001
in which
R40 represents Ci-C6-alkyl or C2-C6-alkenyl, R41 represents Ci-C6-alkyl,
R40 and R41 furthermore together represent C t-Cs-alkanediyl (alkyl) which is mono- or disubstituted by G-Ce-alkyl,
R42 represents bromine or chlorine,
R43 and R47 independently of one another represent hydrogen, fluorine, chlorine or methyl, R44 and R46 independently of one another represent hydrogen or fluorine, R45 represents hydrogen, fluorine or methyl, Group (23): Iodochromones of the general formula (XV)
Figure imgf000014_0002
in which
R48 represents Ci-C6-alkyl,
R49 represents Ci-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl; Group (24): Biphenylcarboxamides of the general formula (XVI) Λ
- 14 -
Figure imgf000015_0001
in which
R50 represents hydrogen or fluorine,
R51 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, trifluoromethoxy, -CH=N-OMe or -C(Me)=N-OMe,
R52 represents hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl, Het represents one of the radicals Hetl to Het7 below:
Figure imgf000015_0002
Hetl Het2 Het3 Het4 Het5 Het6 Het7
R represents iodine, methyl, difluoromethyl or trifluoromethyl, R54 represents hydrogen, fluorine, chlorine or methyl, R55 represents methyl, difluoromethyl or trifluoromethyl,
R56 represents chlorine, bromine, iodine, methyl, difluoromethyl or trifluoromethyl, R57 represents methyl or trifluoromethyl. have very good insecticidal and fungicidal properties.
[0012] According to the invention, "alkyl" represents straight-chain or branched aliphatic hydrocarbons having 1 to 8, preferably 1 to 6, more preferably 1 to 3, carbon atoms. Suitable alkyl groups are, for example, methyl, ethyl, ^-propyl, z'-propyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl. The alkyl group may be unsubstituted or is substituted by at least one of the substituents mentioned here. [0013] According to the invention, "halogen" or "Hal" represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine.
[0014] According to the invention, "haloalkyl" represents alkyl groups having up to 8 carbon atoms in which at least one hydrogen atom has been replaced by a halogen. Suitable haloalkyl groups are, for example, CH2F, CHF2, CF3, CF2C1, CFC12, CC13, CF2Br, CF2CF3, CFHCF3, CH2CF3, CH2CH2F, CH2CHF2, CFC1CF3, CC12CF3, CF2CH3, CF2CH2F, CF2CHF2, CF2CF2C1, CF2CF2Br, CFHCH3, CFHCHF2, CHFCF3, CHFCF2C1, CHFCF2Br, CFC1CF3, CC12CF3, CF2CF2CF3, CH2CH2CH2F, CH2CHFCH3, CH2CF2CF3, CF2CH2CF3, CF2CF2CH3, CHFCF2CF3, CF2CHFCF3, CF2CF2CHF2, CF2CF2CH2F, CF2CF2CF2C1, CF2CF2CF2Br, 1,2,2,2-tetrafluoro-l- (trifluoromethyl)ethyl, 2,2,2-trifluoro-l-(trifluoromethyl)ethyl, pentafluoroethyl, 1- (difluoromethyl)- 1 ,2,2,2-tetrafluoroethyl, 2-bromo- 1 ,2,2-trifluoro- 1 -(trifluoromethyl)ethyl, 1 - (difluoromethyl)-2,2,2-trifluoroethyl. The haloalkyl group may be unsubstituted or is substituted by at least one of the substituents mentioned here.
[0015] Surprisingly, the fungicidal action of the active compound combinations according to the invention is considerably better than the sum of the activities of the individual active compounds. Thus, an unforeseeable true synergistic effect is present, and not just an addition of actions.
[0016] Surprisingly, the insecticidal action of the active compound combinations according to the invention is considerably better than the sum of the activities of the individual active compounds. Thus, an unforeseeable true synergistic effect is present, and not just an addition of actions. [0017] The formula (II) embraces the following preferred mixing partners of group (2):
(2-1) azoxystrobin (known from EP-A 0 382 375) of the formula
Figure imgf000016_0001
fluoxastrobin (known from DE-A 196 02 095) of the formula
Figure imgf000016_0002
(2-3) (2£')-2-(2- {[6-(3-chloro-2-methylphenoxy)-5-fluoro-4-pyrimidinyl]oxy}phenyl)-2-
(methoxyimino)-N-methylethanamide (known from DE-A 196 46 407, EP-B 0 712 396) of the formula
Figure imgf000017_0001
(2-4) trifloxystrobin (known from EP-A 0 460 575) of the formula
Figure imgf000017_0002
(2-5) (2£')-2-(methoxyimino)-N-methyl-2-(2- {[( {(l£')-l -[3-(trifluoromethyl)phenyl]ethylidene} - amino)oxy]methyl}phenyl)ethanamide (known from EP-A 0 569 384) of the formula
Figure imgf000017_0003
(2-6) (2£')-2-(methoxyimino)-N-methyl-2- {2-[(£')-( { l -[3-
(trifluoromethyl)phenyl)ethoxy}imino)methyl]phenyl} ethanamide (known from EP-A 0 596 254) of the formula
Figure imgf000017_0004
orysastrobin (known from DE-A 195 39 324) of the formula
Figure imgf000018_0001
5-methoxy-2-methyl-4-(2- {[( {(l£')-l-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]- methyl}phenyl)-2,4-dihydro-3H-l,2,4-triazol-3-one (known from WO 98/23155) of the formula
Figure imgf000018_0002
kresoxim-methyl (known from EP-A 0 253 213) of the formula
Figure imgf000018_0003
(2-10) dimoxystrobin (known from EP-A 0 398 692) of the formula
Figure imgf000018_0004
(2-1 1) picoxystrobin (known from EP-A 0 278 595) of the fomiula
- I f
(2-12) pyraclostrobin (known from DE-A 44 23 612) of the formula
Figure imgf000019_0001
(2-13) metominostrobin (known from EP-A 0 398 692) of the formula
Figure imgf000019_0002
[0018] The formula (III) embraces the following preferred mixing partners of group (3): (3-1) azaconazole (known from DE-A 25 51 560) of the formula
Figure imgf000019_0003
etaconazole (known from DE-A 25 51 560) of the formula
Figure imgf000019_0004
(3-3) propiconazole (known from DE-A 25 51 560) of the formula
Figure imgf000020_0001
difenoconazole (known from EP-A 0 1 12 284) of the formula
Figure imgf000020_0002
bromuconazole (known from EP-A 0 258 161) of the formula
Figure imgf000020_0003
cyproconazole (known from DE-A 34 06 993) of the formula
Figure imgf000020_0004
hexaconazole (known from DE-A 30 42 303) of the formula
Figure imgf000020_0005
(3-8) penconazole (known from DE-A 27 35 872) of the formula
Figure imgf000021_0001
myclobutanil (known from EP-A 0 145 294) of the formula
Figure imgf000021_0002
(3-10) tetraconazole (known from EP-A 0 234 242) of the formula
Figure imgf000021_0003
(3-11) flutriafol (known from EP-A 0 015 756) of the formula
Figure imgf000021_0004
(3-12) epoxiconazole (known from EP-A 0 196 038) of the formula
Figure imgf000021_0005
(3-13) flusilazole (known from EP-A 0 068 813) of the formula
Figure imgf000022_0001
(3-14) simeconazole (known from EP-A 0 537 957) of the formula
Figure imgf000022_0002
(3-15) prothioconazole (known from WO 96/16048) of the formula
Figure imgf000022_0003
(3-16) fenbuconazole (known from DE-A 37 21 786) of the formula
Figure imgf000022_0004
(3-17) tebuconazole (known from EP-A 0 040 345) of the formula
Figure imgf000022_0005
(3-18) ipconazole (known from EP-A 0 329 397) of the formula „„
- 22 -
Figure imgf000023_0001
(3-19) metconazole (known from EP-A 0 329 397) of the formula
Figure imgf000023_0002
(3-20) triticonazole (known from EP-A 0 378 953) of the formula
Figure imgf000023_0003
(3-21) bitertanol (known from DE-A 23 24 010) of the formula
Figure imgf000023_0004
(3-22) triadimenol (known from DE-A 23 24 010) of the formula
Figure imgf000023_0005
(3-23) triadimefon (known from DE-A 22 01 063) of the formula
Figure imgf000024_0001
(3-24) fluquinconazole (known from EP-A 0 183 458) of the formula
Figure imgf000024_0002
(3-25) quinconazole (known from EP-A 0 183 458) of the formula
Figure imgf000024_0003
[0019] The formula (IV) embraces the following preferred mixing partners of group (4): dichlofluanid (known from DE-A 11 93 498) of the formula
Figure imgf000024_0004
tolylfluanid (known from DE-A 11 93 498) of the formula
Figure imgf000024_0005
[0020] Preferred mixing partners of group (5) are „ Λ
- 24 -
(5-1) iprovalicarb (known from DE-A 40 26 966) of the formula
Figure imgf000025_0001
benthiavalicarb (known from WO 96/04252) of the formula
Figure imgf000025_0002
[0021] The formula (V) embraces the following preferred mixing partners of group (6): (6-1) 2-chloro-N-(l,l,3-trimethylindan-4-yl)nicotinamide (known from EP-A 0 256 503) of the formula
Figure imgf000025_0003
boscalid (known from DE-A 195 31 813) of the formula
Figure imgf000025_0004
furametpyr (known from EP-A 0 315 502) of the formula
Figure imgf000025_0005
(6-4) N-(3-p-tolylthiophen-2-yl)-l-methyl-3-trifluoromethyl-lH-pyrazole-4-carboxamide (known from EP-A 0 737 682) of the formula
Figure imgf000026_0001
ethaboxam (known from EP-A 0 639 574) of the formula
Figure imgf000026_0002
(6-6) fenhexamid (known from EP-A 0 339 418) of the formula
Figure imgf000026_0003
carpropamid (known from EP-A 0 341 475) of the formula
Figure imgf000026_0004
(6-8) 2-chloro-4-(2-fluoro-2-methylpropionylamino)-N,N-dimethylbenzamide
(known from EP-A 0 600 629) of the formula
Figure imgf000026_0005
(6-9) fluopicolid (known from WO 99/42447) of the formula
Figure imgf000027_0001
(6-10) zoxamide (known from EP-A 0 604 019) of the fonnula
Figure imgf000027_0002
(6-12) carboxin (known from US 3,249,499) of the formula
Figure imgf000027_0003
(6-13) tiadinil (known from US 6,616,054) of the formula
Figure imgf000027_0004
(6-14) penthiopyrad (known from EP-A 0 737 682) of the formula
Figure imgf000027_0005
(6-15) silthiofam (known from WO 96/18631 ) of the fonnula
Figure imgf000027_0006
(6-16) N-[2-(l ,3-dimethylbutyl)phenyl]-l-methyl-4-(trifluoiOmethyl)-lH-pynole-3-carboxamide (known from WO 02/38542) of the formula
Figure imgf000028_0001
(6-17) flutolanil (known from DE- A 27 31 522) of the formula
Figure imgf000028_0002
(6-18) N-[2-(l,3-dimethylbutyl)phenyl]-5-fluoro-l,3-dimethyl-lH-pyrazole-4-carboxamide
(known from EP-A 1 414 803) of the formula
Figure imgf000028_0003
(6-20) N-[2-(l,3-dimethylbutyl)phenyl]-2-(trifluoromethyl)benzamide (known from EP-A 1 519 913) of the formula
Figure imgf000028_0004
(6-21) N-[2-(l,3-dimethylbutyl)phenyl]-2-iodobenzamide (known from EP-A 1 519 913) of the formula
Figure imgf000029_0001
(6-22) N-(4'-chloro-3'-fluorobiphenyl-2-yl)-4-(difluoromethyl)-2-methyl-l,3-thiazole-5- carboxamide (known from EP-A 1 404 407) of the formula
Figure imgf000029_0002
(6-24) N-(3',4'-dichlorobiphenyl-2-yl)-2-methyl-4-(trifluoromethyl)-l,3-thiazole-5-carboxamide (known from EP-A 1 474 406) of the formula
Figure imgf000030_0001
[0022] Preferred mixing partners of group (7) are
(7-1) mancozeb (known from DE-A 12 34 704) having the IUPAC name manganese ethylenebis(dithiocarbamate) (polymeric) complex with zinc salt (7-2) maneb (known from US 2,504,404) of the formula
Figure imgf000030_0002
metiram (known from DE-A 10 76 434) having the IUPAC name zinc ammoniate ethylenebis(dithiocarbamate)-poly(ethylenethiuram disulphide) propineb (known from GB 935 981) of the formula
Figure imgf000030_0003
thiram (known from US 1,972,961) of the formula
Figure imgf000030_0004
(7-6) zineb (known from DE-A 10 81 446) of the formula
Figure imgf000031_0001
ziram (known from US 2,588,428) of the formula
Figure imgf000031_0002
[0023] The formula (VI) embraces the following preferred mixing partners of group (8): (8-1) benalaxyl (known from DE-A 29 03 612) of the formula
Figure imgf000031_0003
furalaxyl (known from DE-A 25 13 732) of the formula
Figure imgf000031_0004
(8-3) metalaxyl (known from DE-A 25 15 091 ) of the formula
Figure imgf000031_0005
(8-4) metalaxyl-M (known from WO 96/01559) of the formula _
Figure imgf000032_0001
benalaxyl-M of the formula
Figure imgf000032_0002
[0024] The formula (VII) embraces the following preferred mixing partners of group (9): (9-1) cyprodinil (known from EP-A 0 310 550) of the formula
Figure imgf000032_0003
(9-2) mepanipyrim (known from EP-A 0 270 111) of the formula
Figure imgf000032_0004
pyrimethanil (known from DD 151 404) of the formula
Figure imgf000032_0005
[0025] The formula (VIII) embraces the following preferred mixing partners of group (10):
(10-1) 6-chloro-5-[(3,5-dimethylisoxazol-4-yl)sulphonyl]-2,2-difluoro-5H-[l,3]dioxolo[4,5-f]- benzimidazole (known from WO 97/06171) of the formula
Figure imgf000033_0001
(10-2) benomyl (known from US 3,631,176) of the formula
Figure imgf000033_0002
(10-3) carbendazim (known from US 3,010,968) of the formula
Figure imgf000033_0003
chlorfenazole of the formula
Figure imgf000033_0004
(10-5) fuberidazole (known from DE-A 12 09 799) of the formula
Figure imgf000033_0005
(10-6) thiabendazole (known from US 3,206,468) of the formula
Figure imgf000033_0006
[0026] The formula (IX) embraces the following preferred mixing partners of group (11): (11-1) diethofencarb (known from EP-A 0 078 663) of the formula
Figure imgf000034_0001
(11-2) propamocarb (known from US 3,513 ,241 ) of the formula
Figure imgf000034_0002
(11-3) propamocarb-hydrochloride (known from US 3,513,241) of the formula
Figure imgf000034_0003
(11-4) propamocarb-fosetyl of the formula
Figure imgf000034_0004
[0027] Preferred mixing partners of group (12) are
(12-1) captafol (known from US 3,178,447) of the formula
Figure imgf000034_0005
(12-2) captan (known from US 2,553,770) of the formula
Figure imgf000034_0006
(12-3) folpet (known from US 2,553,770) of the formula
Figure imgf000035_0001
(12-4) iprodione (known from DE-A 21 49 923) of the formula
Figure imgf000035_0002
(12-5) procymidone (known from DE-A 20 12 656) of the formula
Figure imgf000035_0003
(12-6) vinclozolin (known from DE-A 22 07 576) of the formula
Figure imgf000035_0004
[0028] Preferred mixing partners of group (13) are
(13-1) dodine (known from GB 11 03 989) of the formula
Figure imgf000035_0005
(13-2) guazatine (known from GB 11 14 155)
(13-3) iminoctadine triacetate (known from EP-A 0 155 509) of the formula
Figure imgf000036_0001
[0029] Preferred mixing partners of group (14) are
(14-1) cyazofamid (known from EP-A 0 298 196) of the formula
Figure imgf000036_0002
(14-2) prochloraz (known from DE-A 24 29 523) of the formula
Figure imgf000036_0003
(14-3) triazoxide (known from DE-A 28 02 488) of the formula
Figure imgf000036_0004
(14-4) pefurazoate (known from EP-A 0 248 086) of the formula
Figure imgf000036_0005
[0030] The formula (X) embraces the following preferred mixing partners of group (15):
(15-1) aldimorph (known from DD 140 041) of the formula
Figure imgf000037_0001
(15-2) tridemorph (known from GB 988 630) of the formula
Figure imgf000037_0002
(15-3) dodemorph (known from DE-A 25 432 79) of the formula
Figure imgf000037_0003
(15-4) fenpropimorph (known from DE-A 26 56 747) of the formula
Figure imgf000037_0004
(15-5) dimethomorph (known from EP-A 0 219 756) of the formula
Figure imgf000037_0005
(15-6) flumorph (known from EP-A 0 860 438) of the formula
Figure imgf000038_0001
[0031] The formula (XI) embraces the following preferred mixing partners of group (16):
(16-1) fenpiclonil (known from EP-A 0 236 272) of the formula
Figure imgf000038_0002
(16-2) fludioxonil (known from EP-A 0 206 999) of the formula
Figure imgf000038_0003
(16-3) pyrrolnitrin (known from JP 65-25876) of the formula
Figure imgf000038_0004
[0032] Preferred mixing partners of group (17) are (17-1) fosetyl-Al (known from DE-A 24 56 627) of the formula
Figure imgf000039_0001
phosphonic acid (known chemical) of the formula
HO^H^OH (17-3) tolclofos-methyl (known from DE-A 25 01 040) of the formula
Figure imgf000039_0002
[0033] The formula (XII) embraces the following preferred mixing partners of group (18) which are known from WO 96/23793 and can in each case be present as E or Z isomers. Accordingly, compounds of the formula (XII) can 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 (XII) in the form of their E isomer: compound 2-(2,3-dihydro-lH-inden-5-yl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-
(methoxyimino)acetamide of the formula
Figure imgf000039_0003
(18-2) the compound N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(methoxyimino)-2-(5,6,7,8-tetrahydro- naphthalen-2-yl)acetamide of the formula
Figure imgf000039_0004
the compound 2-(4-chlorophenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(methoxyimino) acetamide of the formula
Figure imgf000040_0001
(18-4) the compound 2-(4-bromophenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(methoxyimino)- acetamide of the formula
Figure imgf000040_0002
the compound 2-(4-methylphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(methoxyimino) acetamide of the formula
Figure imgf000040_0003
(18-6) the compound 2-(4-ethylphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(methoxyimino)- acetamide of the formula
Figure imgf000040_0004
[0034] Preferred mixing partners of group (19) are
(19-1) acibenzolar-S-methyl (known from EP-A 0 313 512) of the formula
Figure imgf000040_0005
(19-2) chlorothalonil (known from US 3,290,353) of the formula
Figure imgf000041_0001
(19-3) cymoxanil (known from DE-A 23 12 956) of the formula
Figure imgf000041_0002
(19-4) edifenphos (known from DE-A 14 93 736) of the formula
Figure imgf000041_0003
(19-5) famoxadone (known from EP-A 0 393 911) of the formula
Figure imgf000041_0004
(19-6) fluazinam (known from EP-A 0 031 257) of the formula
Figure imgf000041_0005
(19-7) copper oxychloride
(19-9) oxadixyl (known from DE-A 30 30 026) of the formula
Figure imgf000042_0001
(19-10) spiroxamine (known from DE-A 37 35 555) of the fomiula
Figure imgf000042_0002
dithianon (known from JP-A 44-29464) of the formula
Figure imgf000042_0003
metrafenone (known from EP-A 0 897 904) of the formula
Figure imgf000042_0004
(19-13) 2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)one (known from WO 99/14202) of the formula
Figure imgf000042_0005
(19-14) probenazole (known from US 3,629,428) of the formula
Figure imgf000042_0006
(19-15) isoprothiolane (known from US 3,856,814) of the formula
Figure imgf000043_0001
(19-17) phthalide (known from JP-A 57-55844) of the formula
Figure imgf000043_0002
ferimzone (known from EP-A 0 019 450) of the formula
Figure imgf000043_0003
(19-19) tricyclazole (known from DE-A 22 50 077) of the formula
Figure imgf000043_0004
(19-20) cyprosulfamide of the formula
Figure imgf000044_0001
(19-21) mandipropamid (known from WO 01/87822) of the formula
Figure imgf000044_0002
[0035] Preferred mixing partners of group (20) are
(20-1) pencycuron (known from DE-A 27 32 257) of the formula
Figure imgf000044_0003
(20-2) thiophanate-methyl (known from DE-A 18 06 123) of the formula
Figure imgf000044_0004
(20-3) thiophanate- ethyl (known from DE-A 18 06 123) of the formula
Figure imgf000044_0005
[0036] Preferred mixing partners of group (21) are
(21-1) fenoxanil (known from EP-A 0 262 393) of the formula
Figure imgf000045_0001
(21-2) diclocymet (known from JP-A 7-206608) of the formula
Figure imgf000045_0002
[0037] Preferred mixing partners of group (22) are (22-1) 5-chloro-N-[("7S)-2,2,2-trifluoro-l-methylethyl]-6-(2,4,6-trifluorophenyl)[l,2,4]triazolo- [l,5-a]pyrimidine-7-amine (known from US 5,986,135) of the formula
Figure imgf000045_0003
(22-2) 5-chloro-N-[("7R -l,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[l,2,4]triazolo[l,5-a]- pyrimidine-7-amine (known from WO 02/38565) of the formula
Figure imgf000045_0004
(22-3) 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(4-methylpiperidin-l-yl)[l,2,4]triazolo[l,5-a] pyrimidine (known from US 5,593,996) of the formula
Figure imgf000045_0005
(22-4) 5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-methylpiperidin-l-yl)[l,2,4]triazolo[l,5-a] pyrimidine (known from DE-A 101 24 208) of the formula
Figure imgf000046_0001
[0038] Preferred mixing partners of group (23) are (23-1) 2-butoxy-6-iodo-3-propylbenzopyran-4-one (known from WO 03/014103) of the formula
Figure imgf000046_0002
(23-2) 2-ethoxy-6-iodo-3-propylbenzopyran-4-one (known from WO 03/014103) of the formula
Figure imgf000046_0003
(23-3) 6-iodo-2-propoxy-3-propylbenzopyran-4-one (known from WO 03/014103) of the formula
Figure imgf000046_0004
(23-4) 2-but-2-ynyloxy-6-iodo-3-propylbenzopyran-4-one (known from WO 03/014103) of the formula
Figure imgf000046_0005
(23-5) 6-iodo-2-(l -methylbutoxy)-3-propylbenzopyran-4-one (known from WO 03/014103) of the formula
Figure imgf000047_0001
(23-6) 2-but-3-enyloxy-6-iodobenzopyran-4-one (known from WO 03/014103) of the formula
Figure imgf000047_0002
(23-7) 3-butyl-6-iodo-2-isopropoxybenzopyran-4-one (known from WO 03/014103)
formula
Figure imgf000047_0003
[0039] Preferred mixing partners of group (24) are
(24- 1 ) N-(3',4'-dichloro-5-fluoro- 1 , 1 '-biphenyl-2-yl)-3-(difluoromethyl)- 1 -methyl- lH-pyrazole carboxamide (known from WO 03/070705) of the formula
Figure imgf000047_0004
(24-2) 3 -(difluoromethyl)-N- {3 '-fluoro-4'- [(£ (methoxyimino)methyl] -1,1 '-biphenyl-2-yl} - 1 - methyl-lH-pyrazole-4-carboxamide (known from WO 02/08197) of the formula
Figure imgf000048_0001
(24-3) 3-(trifluoromethyl)-N- {3'-fluoro-4'-[(£)-(methoxyimino)methyl]-l,l'-biphenyl-2-yl} -l- methyl-lH-pyrazole-4-carboxamide (known from WO 02/08197) of the formula
Figure imgf000048_0002
(24-4) N-(3',4'-dichloro- 1 , 1 '-biphenyl-2-yl)-5-fluoro- 1 ,3-dimethyl- lH-pyrazole-4-carboxamide (known from WO 00/14701) of the formula
Figure imgf000048_0003
(24-5) N-(4'-chloro-3'-fluoro-l,r-biphenyl-2-yl)-2-methyl-4-(trifluoromethyl)-l,3-thiazole-5- carboxamide (known from WO 03/066609) of the formula
Figure imgf000048_0004
(24-6) N-(4'-chloro-l, -biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-l,3-thiazole-5-carboxamide (known from WO 03/066610) of the formula
Figure imgf000049_0001
(24-7) N-(4'-bromo-l, -biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-l,3-thiazole-5-carboxamide (known from WO 03/066610) of the formula
Figure imgf000049_0002
(24-8) 4-(difluoromethyl)-2-methyl-N-[4'-(trifluoromethyl)-l,l'-biphenyl-2-yl]-l,3-thiazole-5- carboxamide (known from WO 03/066610) of the formula
Figure imgf000049_0003
[0040] Compound (6-7), carpropamid, has three asymmetrically substituted carbon atoms. Accordingly, compound (6-7) can be present as a mixture of different isomers or else in the form of a single component. Particular preference is given to the compounds
(lS,3R)-2,2-dichloro-N-[(lR)-l-(4-chlorophenyl)ethyl]-l-ethyl-3-methylcyclopropanecarboxamide of the formula
Figure imgf000049_0004
(lR,3S)-2,2-dichloro-N-[(lR)-l-(4-chlorophenyl)ethyl]-l-ethyl-3-methylcyclopropanecarboxamide of the formula
Figure imgf000050_0001
[0041 ] In a preferred embodiment of the present invention, the compounds of the general formula (I) is represented by compounds of formula (1-1):
Figure imgf000050_0002
wherein
Hal represents F, CI, I or Br; and
X' represents Ci-Ce alkyl or substituted Ci-Ce alkyl having at least one substituent selected from the group consisting of halogen, hydroxy, cyano, nitro, amino, halo C1-C3 alkyl group, preferably a Ci-C6cyanoalkyl; A' represents C1-C3 alkyl, C1-C3 haloalkyl, halogen, preferably methyl, halomethyl, ethyl or haloethyl, more preferably methyl or ethyl; n represents 0, 1, 2, 3 or 4, preferably 0, 1 or 2, more preferably 1.
[0042] In a more preferred embodiment of the present invention, a composition comprises at least one compound of the general formula (I) selected from the group consisting of compound (1-2), (1-3), (1-4) or (1-5):
Figure imgf000050_0003
(1-2)
Figure imgf000051_0001
Figure imgf000051_0002
Figure imgf000051_0003
[0043] Even more preferably, a compound of formula (I) is selected from the group consisting of compound (1-2) or compound (1-5).
[0044] In one preferred embodiment, the compound of formula (I) is compound (1-5).
[0045] Particularly preferred active compounds of groups (2) to (24) are the following active compounds:
(2-1) azoxystrobin
(2-2) fluoxastrobin
(2-3) (2£')-2-(2- {[6-(3-chloro-2-methylphenoxy)-5-fluoro-4-pyrimidinyl]oxy}phenyl)-2-
(methoxyimino)-N-methylethanamide
(2-4) trifloxystrobin
(2-5) (2£)-2-(methoxyimino)-N-methyl-2-(2- {[( {(l£)-l -[3-(trifluoromethyl)- phenyl]ethylidene} amino)oxy]methyl}phenyl)ethanamide
(2-6) (2£)-2-(methoxyimino)-N-methyl-2- {2- [(£)-( { 1 - [3 -(trifluoromethyl)phenyl] - ethoxy} imino)methyl]phenyl} ethanamide (2-8) 5-methoxy-2-methyl-4-(2- {[( {(l£)-l-[3-(trifluoromethyl)phenyl]ethylidene}- amino)oxy]methyl}phenyl)-2,4-dihydro-3H- 1 ,2,4-triazol-3-one
2-9) kresoxim-methyl
2-10) dimoxysti-obin
2-11) picoxystrobin
2- 12) pyraclostrobin
2- 13) metominostrobin
3- 3) propiconazole
3-4) difenoconazole
3-6) cyproconazole
3-7) hexaconazole
3-8) penconazole
3-9) myclobutanil
3-10) tetraconazole
3-12) epoxiconazole
3-13) flusilazole
3-15) prothioconazole
3-16) fenbuconazole
3-17) tebuconazole
3-18) ipconazole
3-19) metconazole
3-20) triticonazole
3-21) bitertanol
3-22) triadimenol
3-23) triadimefon
3- 24) fluquinconazole
4- 1) dichlofluanid
4- 2) tolylfluanid
5- 1) iprovalicarb
5- 3) benthiavalicarb
6- 2) boscalid
6-5) ethaboxam
6-6) fenhexamid
6-7) carpropamid
8) 2-chloiO-4-[(2-fluoro-2-methylpropanoyl)amino]-N,N-dimethylbenzamide
6-9) fluopicolid
6-10) zoxamide 6-11) 3,4-dichloro-N-(2-cyanophenyl)isothiazole-5-carboxamide
6-14) penthiopyrad
6- 16) N-[2-(l ,3-dimethylbutyl)phenyl]- 1 -methyl-4-(trifluoromethyl)- lH-pyrrole-3-carboxamide
6-17) flutolanil
6-18) N-[2-(l,3-dimethylbutyl)phenyl]-5-fluoro-l,3-dimethyl-lH-pyrazole-4-carboxamide
7-1 mancozeb
7-2 maneb
7-4 propineb
7-5 thiram
7- 6 zineb
8- 1 benalaxyl
8-2 furalaxyl
8-3 metalaxyl
8- 4 metalaxyl-M
5 benalaxyl-M
9- 1 cyprodinil
9-2 mepanipyrim
9- 3 pyrimethanil
10- 6-chloro-5-[(3,5-dimethylisoxazol-4-yl)sulphonyl]-2,2-difluoro-5H-[l ,3]dioxolo[4,5-fl- benzimidazole
10- : carbendazim
1 1- diethofencarb
1 1 - : propamocarb
1 1 - : propamocarb-hydrochloride
11- propamocarb-fosetyl
12- : captan
12-: folpet
12- iprodione
12- procymidone
13- dodine
13- guazatine
13- iminoctadine triacetate
14- cyazofamid
14- prochloraz
14- triazoxide
15- fenpropimorph
15- dimethomorph (15-6) flumorph
(16-2) fludioxonil
(17-1) fosetyl-Al
(17-2) phosphonic acid
(17-3) tolclofos-methyl
(19-1) acibenzolar-S-methyl
(19-2) chlorothalonil
(19-3) cymoxanil
(19-5) famoxadone
(19-6) fluazinam
(19-7) copper oxychloride
(19-9) oxadixyl
(19-10) spiroxamine
(19-21) cyprosulfamide
(19-22) mandipropamid
(20-1) pencycuron
(20-2) thiophanate-methyl
(22-1) 5-chloro-N-[^S 2,2,2-trifluoro-l-methylethyl]-6-(2,4,6-trifluorophenyl)[l,2,4]- triazolo[l ,5-a]pyrimidine-7-amine
(22-2) 5-chloro-N-[(7R l,2-dimemylpropyl]-6-(2,4,6-trifluorophenyl)[l,2,4]triazolo[l,5-a]- pyrimidine-7-amine
(22-4) 5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-methylpiperidin-l-yl)[l,2,4-triazolo[l,5- ajpyrimidine
(23-1) 2-butoxy-6-iodo-3-propylbenzopyran-4-one
(23-2) 2-ethoxy-6-iodo-3-propylbenzopyran-4-one
(23-3) 6-iodo-2-propoxy-3-propylbenzopyran-4-one
(24- 1 ) N-(3',4'-dichloro-5-fluoro- 1 , 1 '-biphenyl-2-yl)-3-(difluoromethyl)- 1 -methyl- lH-pyrazole-4- carboxamide
(24-3) 3-(trifluoromethyl)-N- {3'-fluoro-4'-[(£')-(methoxyimino)methyl]-l,l'-biphenyl-2-yl} -l- methyl-lH-pyrazole-4-carboxamide
(24-7) N-(4'-bromo-l, -biphenyl-2-yl)-4-(difluoromethyl)-2-methyl-l,3-thiazole-5-carboxamide.
[0046] Very particularly preferred active compounds of the groups (2) to (24) are the following active compounds: (2-2) fluoxastrobin
(2-3) (2£')-2-(2- {[6-(3-chloro-2-methylphenoxy)-5-fluoro-4-pyrimidinyl]oxy}phenyl)-2- (methoxyimino)-N-methylethanamide (2-4) trifloxystrobin
(3-15) prothioconazole
(3-17) tebuconazole
(3-18) ipconazole
(3-20) triticonazole
(3-21) bitertanol
(3-22) triadimenol
(3-24) fluquinconazole
(4-1) dichlofluanid
(4-2) tolylfluanid
(5-1) iprovalicarb
(6-6) fenhexamid
(6-7) carpropamid
(6-9) fluopicolid
(6-14) penthiopyrad
(6-17) flutolanil
(6-18) N-[2-(l,3-dimethylbutyl)phenyl]-5-fluoro-l,3-dimethyl-lH-pyrazole-4-carboxamide
(7-4) propineb
(7-5) thiram
(8-3) metalaxyl
(8-4) metalaxyl-M
(8-5) benalaxyl-M
(9-3) pyrimethanil
(10-3) carbendazim
(11-4) propamocarb-fosetyl
(12-4) iprodione
(14-2) prochloraz
(14-3) triazoxide
(16-2) fludioxonil
(17-3) tolclofos-methyl
(19-10) spiroxamine
(19-21) cyprosulfamide
(19-22) mandipropamid
(20- 1 ) pencycuron
(22-4) 5-chloiO-6-(2,4,6-trifluorophenyl)-7-(4-methylpiperidin-l-yl)[l ,2,4]triazolo[l ,5-a]- pyrimidine (24- 1 ) N-(3',4'-dichloro-5-fluoro- 1 , 1 '-biphenyl-2-yl)-3-(difluoromethyl)- 1 -methyl- lH-pyrazole-4- carboxamide.
[0047] Especially preferred mixing partners are the following active compounds:
(2-2) fluoxastrobin
(2-4) trifloxystrobin
(3-15) prothioconazole
(3-17) tebuconazole
(3-18) ipconazole
(3-20) triticonazole
(3-22) triadimenol
(6-7) carpropamid
(6-18) N-[2-(l,3-dimethylbutyl)phenyl]-5-fluoro-l,3-dimethyl-lH-pyrazole-4-carboxamide
(7-5) thiram
(8-3) metalaxyl
(8-4) metalaxyl-M
(19-21) cyprosulfamide
(20-1) pencycuron
(24- 1 ) N-(3',4'-dichloro-5-fluoro- 1 , 1 '-biphenyl-2-yl)-3-(difluoromethyl)- 1 -methyl- lH-pyrazole- 4-carboxamide.
[0048] Active compound combinations which are to be emphasized are listed in the table below.
Active compound of group I Active compound of groups 2 to 24
(1-2) (2-2) fluoxastrobin
(1-2) (2-4) trifloxystrobin
(1-2) (3-15) prothioconazole
(1-2) (3-17) tebuconazole
(1-2) (3-18) ipconazole
(1-2) (3-20) triticonazole
(1-2) (3-22) triadimenol
(1-2) (6-7) carpropamid
(1-2) (6-18) N-[2-(l,3-dimethylbutyl)phenyl]-5-fluoro-l,3-dimethyl- 1 H-pyrazole-4-carboxamide
(1-2) (7-5) thiram
(1-2) (8-3) metalaxyl Active compound of group I Active compound of groups 2 to 24
(1-2) (8-4) metalaxyl-M
(1-2) (19-21) cyprosulfamide
(1-2) (20-1) pencycuron
(1-2) (24- 1 ) N-(3 ',4'-dichloro-5-fluoro- 1 , 1 '-biphenyl-2-yl)-3 -
(difluoromethyl)- 1 -methyl- lH-pyrazole-4-carboxamide
(1-2) (2-2) fluoxastrobin
(1-2) (2-4) trifloxystrobin
(1-2) (3-15) prothioconazole
(1-2) (3-17) tebuconazole
(1-2) (3-18) ipconazole
(1-2) (3-20) triticonazole
(1-2) (3-22) triadimenol
(1-2) (6-7) carpropamid
(1-2) (6-18) N-[2-(l,3-dimethylbutyl)phenyl]-5-fluoro-l,3-dimethyl- 1 H-pyrazole-4-carboxamide
(1-2) (7-5) thiram
(1-2) (8-3) metalaxyl
(1-2) (8-4) metalaxyl-M
(1-2) (19-21) cyprosulfamide
(1-2) (20-1) pencycuron
(1-2) (24- 1 ) N-(3 ',4'-dichloro-5-fluoro- 1 , 1 '-biphenyl-2-yl)-3 -
(difluoromethyl)- 1 -methyl- lH-pyrazole-4-carboxamide
(1-5) (2-2) fluoxastrobin
(1-5) (2-4) trifloxystrobin
(1-5) (3-15) prothioconazole
(1-5) (3-17) tebuconazole
(1-5) (3-18) ipconazole
(1-5) (3-20) triticonazole
(1-5) (3-22) triadimenol
(1-5) (6-7) carpropamid
(1-5) (6-18) N-[2-(l,3-dimethylbutyl)phenyl]-5-fluoro-l,3-dimethyl- 1 H-pyrazole-4-carboxamide
(1-5) (7-5) thiram
(1-5) (8-3) metalaxyl
(1-5) (8-4) metalaxyl-M Active compound of group I Active compound of groups 2 to 24
(1-5) (19-21) cyprosulfamide
(1-5) (20-1) pencycuron
(1-5) (24- 1 ) N-(3 ',4'-dichloro-5-fluoro- 1 , 1 '-biphenyl-2-yl)-3 -
(difluoromethyl)- 1 -methyl- lH-pyrazole-4-carboxamide
(1-5) (2-2) fluoxastrobin
(1-5) (2-4) trifloxystrobin
(1-5) (3-15) prothioconazole
(1-5) (3-17) tebuconazole
(1-5) (3-18) ipconazole
(1-5) (3-20) triticonazole
(1-5) (3-22) triadimenol
(1-5) (6-7) carpropamid
(1-5) (6-18) N-[2-(l,3-dimethylbutyl)phenyl]-5-fluoro-l,3-dimethyl- 1 H-pyrazole-4-carboxamide
(1-5) (7-5) thiram
(1-5) (8-3) metalaxyl
(1-5) (8-4) metalaxyl-M
(1-5) (16-2) Fludioxonil
(1-5) (19-21) cyprosulfamide
(1-5) (20-1) pencycuron
(1-5) (24- 1 ) N-(3 ',4'-dichloro-5-fluoro- 1 , 1 '-biphenyl-2-yl)-3 -
(difluoromethyl)- 1 -methyl- lH-pyrazole-4-carboxamide
[0049] Embodiments of the invention which are emphasized for the treatment of seed are mixtures comprising a compound selected from the group (I) consisting of compound (1-2), (1-3), (1 -4) and (1-5) and a compound selected from the group consisting of fluoxastrobin (2-2) and/or trifloxystrobin (2-4) and/or prothioconazole (3-15) and/or tebuconazole (3-17) and/or ipconazole (3-18) and/or triticonazole (3-20) and/or triadimenol (3-22) and/or carpropamid (6-7) and/or N-[2- ( 1 ,3 -dimethylbutyl)phenyl] -5 -fluoro- 1 ,3 -dimethyl- 1 H-pyrazole-4-carboxamide (6-18) and/ or thiram (7-5) and/or metalaxyl (8-3) and/or metalaxyl-M (8-4) and/or N-({4- [(cyclopropylamino)carbonyl]phenyl}sulphonyl)-2-methoxybenzamide (19-21) and/or pencycuron (20-1) and/or N-(3',4'-dichloro-5-fluoro-l,l'-biphenyl-2-yl)-3-(difluoromethyl)-l -methyl-lH- pyrazole-4-carboxamide (24-1).
[0050] Embodiments of the invention which are emphasized for the treatment of seed are furthermore mixtures comprising a compound selected from the group (I) consisting of compound (1-2), (1-3), (1-4) and (1-5) and a compound selected from the group consisting of fluoxastrobin (2- 2) and/or trifloxystrobin (2-4) and/or prothioconazole (3-15) and/or tebuconazole (3-17) and/or ipconazole (3-18) and/or triticonazole (3-20) and/or triadimenol (3-22) and/or carpropamid (6-7) and/or N-[2-(l,3-dimethylbutyl)phenyl]-5-fluoro-l,3-dimethyl-lH-pyrazole-4-carboxamide (6-18) and/or thiram (7-5) and/or metalaxyl (8-3) and/or metalaxyl-M (8-4) and/or N-({4- [(cyclopropylamino)carbonyl]phenyl}sulphonyl)-2-methoxybenzamide (19-21) and/or pencycuron (20- 1 ) and/or N-(3',4'-dichloro-5-fluoro- 1 , 1 '-biphenyl-2-yl)-3 -(difluoromethyl)- 1 -methyl- 1H- pyrazole-4-carboxamide (24-1).
[0051] In addition to an active compound of the formula (I), the active compound combinations according to the invention comprise at least one active compound from the compounds of groups (2) to (24). In addition, they may also comprise further fungicidally active additives.
[0052] The synergistic effect is particularly pronounced when the active compounds in the active compound combinations according to the invention are present in certain weight ratios. However, the weight ratios of the active compounds in the active compound combinations can be varied within a relatively wide range. In general, the combinations according to the invention comprise an active compound of the formula (I) and one of the active compounds of group (2) to (24) in the following preferred and particularly preferred mixing ratios:
Preferred mixing ratio : 125:1 to 1 :125
More preferred mixing ratio: 40: 1 to 1 :40 Particularly preferred mixing ratio: 25: 1 to 1 :25
[0053] In the range of 25: 1 to 1 :25, mixing ratios are, e.g. 20: 1 to 1 :20, 15: 1 to 1 : 15, 10: 1 to 1 : 10, 5: 1 to 1 :5, 3: 1 to 1 :3, 2: 1 to 1 :2 or combinations thereof such as 20:1 to 1 :5 or 5: 1 to 1 :3.
[0054] In one preferred embodiment, a combination according to the invention is characterized in that compound (I) is compound (1-5) and an active compound of group (2) to (24) is selected from the group consisting of Metalaxyl (8-3), Cyproconazole (3-6), Fludioxonil (16-2), and Propamocarb-hydrochloride (11-3).
[0055] For example, preferred mixing ratios for a combination of compound (1-5) and Metalaxyl (8-3) are 2: 1 to 1 : 100, more preferably 1 : 1 to 1 : 100.
[0056] For example, preferred mixing ratios for a combination of compound (1-5) and Cyproconazole (3-6) are 1 : 1 to 1 :15, more preferably 1 :4 to 1 : 12. [0057] Further preferred mixing ratios for a combination of compound (1-5) and Fludioxonil (16- 2) are 2: 1 to 1 :200, more preferably 1,25:1 to 1 :170.
[0058] Further preferred mixing ratios for a combination of compound (1-5) and Propamocarb- hydrochloride (11-3) are 1 : 1 to 1 :200, more preferably 4: 1 to 1 :170. [0059] The mixing ratios are based on weight ratios. The ratio is to be understood as meaning active compound of the formula (I) : active compound of any one of groups (2) to (24).
[0060] The active compound combinations according to the invention, in combination with good plant tolerance and favourable toxicity to warm-blooded animals and being tolerated well by the environment, are suitable for protecting plants and plant organs, for increasing the harvest yields, for improving the quality of the harvested material and for controlling animal pests, in particular insects, arachnids, helminths, nematodes and molluscs, which are encountered in agriculture, in horticulture, in animal husbandry, in forests, in gardens and leisure facilities, in the protection of stored products and of materials, and in the hygiene sector. They may be preferably employed as plant protection agents. They are active against normally sensitive and resistant species and against all or some stages of development. The abovementioned pests include pests: from the order of the Anoplura (Phthiraptera), from the class of the Arachnida, from the class of the Bivalva, from the order of the Chilopoda, from the order of the Coleoptera, from the order of the Collembola, from the order of the Dermaptera, from the order of the Diplopoda, from the order of the Diptera, from the class of the Gastropoda, from the class of the helminths, it is furthermore possible to control protozoa, from the order of the Heteroptera, from the order of the Homoptera, from the order of the Hymenoptera, from the order of the Isopoda, from the order of the Isoptera, from the order of the Lepidoptera, from the order of the Orthoptera, from the order of the Siphonaptera, from the order of the Symphyla, from the order of the Thysanoptera, from the order of the Thysanura, phytoparasitic nematodes. [0061] If appropriate, the active compound combinations according to the invention can, at certain concentrations or application rates, also be used as herbicides, safeners, growth regulators or agents to improve plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including agents against viroids) or as agents against MLO (Mycoplasma- like organisms) and RLO (Rickettsia- like organisms). If appropriate, they can also be employed as intermediates or precursors for the synthesis of other active compounds.
[0062] All plants and plant parts can be treated in accordance with the invention. Plants are to be understood as meaning in the present context 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 plant breeding and optimization methods or by rn
- 60 - biotechnological and genetic engineering methods or by combinations of these methods, including the transgenic plants and including the plant cultivars protectable or not protectable by plant breeders' rights. Plant parts are to be understood as meaning all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, stems, flowers, fruit bodies, fruits and seeds and also roots, tubers and rhizomes. The plant parts also include harvested material, and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
[0063] Treatment according to the invention of the plants and plant parts with the active compound combinations is carried out directly or by allowing the compounds to act on the surroundings, habitat or storage space by the customary treatment methods, for example by immersion, spraying, evaporation, fogging, scattering, painting on, injection and, in the case of propagation material, in particular in the case of seeds, also by applying one or more coats.
[0064] The active compound combinations according to the invention are particularly suitable for treating seed. Here, the combinations according to the invention mentioned above as preferred or particularly preferred may be mentioned as being preferred. Thus, a large part of the damage to crop plants which is caused by pests occurs as early as when the seed is attacked during storage and after the seed is introduced into the soil, and during and immediately after germination of the plants. This phase is particularly critical since the roots and shoots of the growing plant are particularly sensitive and even minor damage can lead to the death of the whole plant. Protecting the seed and the germinating plant by the use of suitable compositions is therefore of particularly great interest.
[0065] The control of pests by treating the seeds of plants has been known for a long time and is the subject of continuous improvements. However, the treatment of seed entails a series of problems which cannot always be solved in a satisfactory manner. Thus, it is desirable to develop methods for protecting the seed and the germinating plant which dispense with the additional application of crop protection agents after sowing or after the emergence of the plants. It is furthermore desirable to optimize the amount of active compound employed in such a way as to provide maximum protection for the seed and the germinating plant from attack by pests, but without damaging the plant itself by the active compound employed. In particular, methods for the treatment of seed should also take into consideration the intrinsic insecticidal properties of transgenic plants in order to achieve optimum protection of the seed and also the germinating plant with a minimum of crop protection agents being employed.
[0066] Accordingly, the present invention relates in particular also to a method for protecting seed and germinating plants against attack by pests which comprises treating the seed with an active compound combination according to the invention. The method according to the invention for „
- 61 - protecting seed and germinating plants against attack by pests comprises a method wherein the seed is treated simultaneously with an active compound of the formula I and one of the active compounds of group (2) to (24). The invention also comprises a method wherein the seed is treated at different times with an active compound of the formula I and one of the active compounds of group (2) to (24). The invention also relates to the use of the active compound combinations according to the invention for treating seed for protecting the seed and the plant emerging therefrom against pests. Furthermore, the invention relates to seed treated with an active compound combination according to the invention for protection against pests. The invention also relates to seed treated simultaneously with an active compound of the formula I and one of the active compounds of group (2) to (24). The invention furthermore relates to seed treated at different times with an active compound of the formula I and one of the active compounds of group (2) to (24). In the case of seed treated at different times with an active compound of the formula I and one of the active compounds of group (2) to (24), the individual active compounds of the composition according to the invention, may be present in different layers on the seed. Here, the layers comprising an active compound of the formula I and one of the active compounds of group (2) to (24) may optionally be separated by an intermediate layer. The invention also relates to seed where an active compound of the formula I and one of the active compounds of group (2) to (24) are applied as component of a coating or as a further layer or further layers in addition to a coating.
[0067] One of the advantages of the present invention is that the particular systemic properties of the active compound combinations according to the invention mean that treatment of the seed with these active compound combinations not only protects the seed itself, but also the resulting plants after emergence, from pests. In this manner, the immediate treatment of the crop at the time of sowing or shortly thereafter can be dispensed with.
[0068] A further advantage is the synergistically increased insecticidal activity of the active compound combinations according to the invention in comparison with the insecticidal individual active compound, which exceeds the expected activity of the two active compounds when applied individually. Also advantageous is the synergistically increased fungicidal activity of the active compound combinations according to the invention in comparison with the fungicidal individual active compound, which exceeds the expected activity of the active compound when applied individually. This makes possible an optimization of the amount of active compounds employed.
[0069] It is likewise to be considered as advantageous that the active compound combinations according to the invention can be employed also in particular in transgenic seed, the plants arising from this seed being capable of expressing a protein directed against pests. By treating such seed with the active compound combinations according to the invention, certain pests can be controlled merely by the expression of the, for example, insecticidal protein, and additionally be protected by the active compound combinations according to the invention against damage. _
- 62 -
[0070] The active compound combinations according to the invention are suitable for protecting seed of any plant variety as already mentioned above which is employed in agriculture, in the greenhouse, in forests or in horticulture. In particular, this takes the form of seed of maize, peanut, canola, oilseed rape, poppy, soya beans, cotton, beet (for example sugar beet and fodder beet), rice, sorghum and millet, wheat, barley, oats, rye, sunflower, tobacco, potatoes or vegetables (for example tomatoes, cabbage plants). The active compound combinations according to the invention are likewise suitable for treating the seed of fruit plants and vegetables as already mentioned above. The treatment of the seed of maize, soya beans, cotton, wheat and canola or oilseed rape is of particular importance. [0071] As already mentioned above, the treatment of transgenic seed with an active compound combination according to the invention is also of particular importance. This takes the form of seed of plants which, as a rule, comprise at least one heterologous gene which governs the expression of a polypeptide with in particular insecticidal properties. In this context, the heterologous genes in transgenic seed may be derived from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly suitable for the treatment of transgenic seed which comprises at least one heterologous gene originating from Bacillus sp. and whose gene product shows activity against the European corn borer and/or the corn root worm. It is particularly preferably a heterologous gene derived from Bacillus thuringiensis . [0072] In the context of the present invention, the active compound combination according to the invention is applied to the seed either alone or in a suitable formulation. Preferably, the seed is treated in a state which is stable enough to avoid damage during treatment. In general, the seed may be treated at any point in time between harvest and sowing. The seed usually used has been separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits. [0073] When treating the seed, care must generally be taken that the amount of the active compound combination according to the invention applied to the seed and/or the amount of further additives is chosen in such a way that the germination of the seed is not adversely affected, or that the resulting plant is not damaged. This must be borne in mind in particular in the case of active compounds which may have phytotoxic effects at certain application rates. [0074] The active compound combinations can be converted to the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, granules for broadcasting, suspension-emulsion concentrates, natural materials impregnated with active compound, synthetic materials impregnated with active compound, fertilizers and microencapsulations in polymeric substances. _
- 63 -
[0075] These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants and/or foam-formers. The formulations are prepared either in suitable plants or else before or during the application. [0076] Suitable for use as auxiliaries are substances which are suitable for imparting to the composition itself and/or to preparations derived therefrom (for example spray liquors, seed dressings) particular properties such as certain technical properties and/or also particular biological properties. Typical suitable auxiliaries are: extenders, solvents and carriers.
[0077] Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, for example from the classes of the aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, if appropriate, may also be substituted, etherified and/or esterified), the ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly)ethers, the unsubstituted and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulphones and sulphoxides (such as dimethyl sulphoxide).
[0078] If the extender used is water, it is also possible to employ, for example, organic solvents as auxiliary solvents. Essentially, suitable liquid solvents are: 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, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and also their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl sulphoxide, and also water.
[0079] 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 ground synthetic minerals, such as finely divided silica, alumina and silicates; suitable solid carriers for granules are: for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic meals, and granules of organic material such as paper, sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam-formers are: for example, nonionic and anionic emulsifiers, such as polyoxy ethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and also protein hydrolysates; suitable dispersants are nonionic and/or ionic substances, for example from the classes of the alcohol-POE and/or -POP ethers, acid and/or POP-POE esters, alkyl aryl and/or POP- POE ethers, fat- and/or POP-POE adducts, POE- and/or POP-polyol derivatives, POE- and/or POP-sorbitan- or -sugar adducts, alkyl or aryl sulphates, alkyl- or arylsulphonates and alkyl or aryl phosphates or the „ Λ
- 64 - corresponding PO-ether adducts. Furthermore, suitable oligo- or polymers, for example those derived from vinylic monomers, from acrylic acid, from EO and/or PO alone or in combination with, for example, (poly)alcohols or (poly)amines. It is also possible to employ lignin and its sulphonic acid derivatives, unmodified and modified celluloses, aromatic and/or aliphatic sulphonic acids and their adducts with formaldehyde.
[0080] Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. [0081] It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
[0082] Other possible additives are perfumes, mineral or vegetable, optionally modified oils, waxes and nutrients (including trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
[0083] Stabilizers, such as low-temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve chemical and/or physical stability may also be present.
[0084] The formulations generally comprise between 0.01 and 98% by weight of active compound, preferably between 0.5 and 90%.
[0085] The active compound combinations according to the invention, in commercially available formulations and in the use forms prepared from these formulations, can be present in a mixture with other active compounds such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators or herbicides. The insecticides include, for example, phosphoric esters, carbamates, carboxylic esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, and the like.
[0086] A mixture with other known active compounds, such as herbicides, or with fertilizers and growth regulators is also possible.
[0087] When used as insecticides, the active compound combinations according to the invention can furthermore be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with synergistic agents. Synergistic agents are compounds which increase the action of the active compounds, without it being necessary for the synergistic agent added to be active itself.
[0088] The active compound content of the use forms prepared from the commercially available formulations can vary within wide limits. The active compound concentration of the use forms can be from 0.00000001 to 95% by weight of active compound, preferably between 0.00001 and 1% by weight.
[0089] Application is in a manner appropriate for the use forms.
[0090] As already mentioned above, it is possible to treat all plants and their parts according to the invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The terms "parts", "parts of plants" and "plant parts" have been explained above.
[0091] Particularly preferably, plants of the plant cultivars which are in each case commercially available or in use are treated according to the invention. Plant cultivars are to be understood as meaning plants having novel properties ("traits") which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, bio- or genotypes.
[0092] Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive ("synergistic") effects. Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity 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 drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products are possible, which exceed the effects which were actually to be expected.
[0093] The plants listed can be treated in a particularly advantageous manner with the active compound combinations according to the invention. The preferred ranges stated above for the active compound combinations also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the active compound combinations specifically mentioned in the present text. - 66 -
[0094] The active compound combinations according to the invention act not only against plant, hygiene and stored product pests, but also in the veterinary medicine sector against animal parasites (ecto- and endoparasites), such as hard ticks, soft ticks, mange mites, leaf mites, flies (biting and licking), parasitic fly larvae, lice, hair lice, feather lice and fleas. These parasites include: [0095] From the order of the Anoplurida, from the order of the Mallophagida and the suborders Amblycerina and Ischnocerina, from the order of the Diptera and the suborders Nematocerina and Brachycerina, from the order of the Siphonapterida, from the order of the Heteropterida, from the order of the Blattarida, from the subclass of the Acari (Acarina) and the orders of the Meta- and Mesostigmata, from the order of the Actinedida (Prostigmata) and Acaridida (Astigmata). [0096] The active compound combinations according to the invention are also suitable for controlling arthropods which infest agricultural productive livestock, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese and bees, other pets, such as, for example, dogs, cats, caged birds and aquarium fish, and also so-called test animals, such as, for example, hamsters, guinea pigs, rats and mice. By controlling these arthropods, cases of death and reduction in productivity (for meat, milk, wool, hides, eggs, honey etc.) should be diminished, so that more economic and easier animal husbandry is possible by use of the active compound combinations according to the invention.
[0097] The active compound combinations according to the invention are used in the veterinary sector and in animal husbandry in a known manner by enteral administration in the form of, for example, tablets, capsules, potions, drenches, granules, pastes, boluses, the feed-through process and suppositories, by parenteral administration, such as, for example, by injection (intramuscular, subcutaneous, intravenous, intraperitoneal and the like), implants, by nasal administration, by dermal use in the form, for example, of dipping or bathing, spraying, pouring on and spotting on, washing and powdering, and also with the aid of moulded articles containing the active compounds, such as collars, ear marks, tail marks, limb bands, halters, marking devices and the like.
[0098] When used for cattle, poultry, pets and the like, the active compound combinations can be used as formulations (for example powders, emulsions, free-flowing compositions), which comprise the active compounds in an amount of 1 to 80% by weight, directly or after 100 to 10 000-fold dilution, or they can be used as a chemical bath.
[0099] It has furthermore been found that the active compound combinations according to the invention have a strong insecticidal action against insects which destroy industrial materials.
[0100] The following insects may be mentioned as examples and as preferred - but without any limitation: Beetles, Hymenopterons, Termites, Bristletails. „
- 67 -
[0101] Industrial materials in the present connection are to be understood as meaning non-living materials, such as, preferably, plastics, adhesives, sizes, papers and cardboards, leather, wood and processed wood products and coating compositions.
[0102] The ready-to-use compositions may, if appropriate, comprise further insecticides and, if appropriate, one or more fungicides.
[0103] With respect to possible additional additives, reference may be made to the insecticides and fungicides mentioned above.
[0104] The active compound combinations according to the invention can likewise be employed for protecting objects which come into contact with seawater or brackish water, in particular hulls, screens, nets, buildings, moorings and signalling systems, against fouling.
[0105] Furthermore, the active compound combinations according to the invention, alone or in combinations with other active compounds, may be employed as antifouling agents.
[0106] In domestic, hygiene and stored-product protection, the active compound combinations are also suitable for controlling animal pests, in particular insects, arachnids and mites, which are found in enclosed spaces such as, for example, dwellings, factory halls, offices, vehicle cabins and the like. They can be employed alone or in combination with other active compounds and auxiliaries in domestic insecticide products for controlling these pests. They are active against sensitive and resistant species and against all developmental stages. These pests include:
[0107] From the order of the Scorpionidea, Acarina, Araneae, Opiliones, Isopoda, Diplopoda, Chilopoda, Zygentoma, Blattaria, Saltatoria, Dermaptera, Isoptera, Psocoptera, Coleoptera, Diptera, Lepidoptera, Siphonaptera, Hymenoptera, Anoplura, Heteroptera.
[0108] In the field of household insecticides, they are used alone or in combination with other suitable active compounds, such as phosphoric esters, carbamates, pyrethroids, neonicotinoids, growth regulators or active compounds from other known classes of insecticides. [0109] They are used in aerosols, pressure- free spray products, for example pump and atomizer sprays, automatic fogging systems, foggers, foams, gels, evaporator products with evaporator tablets made of cellulose or polymer, liquid evaporators, gel and membrane evaporators, propeller- driven evaporators, energy- free, or passive, evaporation systems, moth papers, moth bags and moth gels, as granules or dusts, in baits for spreading or in bait stations. [0110] The good insecticidal and acaricidal activity of the active compound combinations according to the invention is illustrated by the examples below. Whereas the individual active compounds show weaknesses in their activity, the combinations show an activity which exceeds a simple addition of activities.
[0111] A synergistic effect in insecticides and acaricides is always present when the activity of the active compound combinations exceeds the total of the activities of the active compounds when applied individually.
[0112] The expected activity for a given combination of two active compounds can be calculated according to S.R. Colby, Weeds 15 (1967), 20-22 as follows:
If
X is the kill rate, expressed in % of the untreated control, when active compound A is applied at an application rate of m g/ha or at a concentration of m ppm,
Y is the kill rate, expressed in % of the untreated control, when active compound B is applied at an application rate of n g/ha or at a concentration of n ppm and
E is the kill rate, expressed in % of the untreated control, when active compounds A and B is applied at application rates of m and n g/ha or at a concentration of m and n ppm, then
X Y
E=X + Y- 1 00
[0113] If the actual kill rate is greater than calculated, the kill of the combination is superadditive, i.e. there is a synergistic effect. In this case, the actual observed kill rate has to be greater than the value for the expected kill rate (E) calculated from the formula given above.
Example A
Spodoptera frugiperda - spray test
Solvent: 78.0 parts by weight acetone
1.5 parts by weight dimethylformamide
Emulsifier: 0.5 parts by weight alkylarylpolyglycolether
[0114] To produce a suitable preparation of the active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and emulsifier, and the concentrate is diluted with emulsifier- containing water to the desired concentration.
[0115] Maize (Zea mais) leaf sections are sprayed with a preparation of the active ingredient of the desired concentration. Once dry, the leaf sections are infested with fall armyworm larvae (Spodoptera frugiperda).
[0116] After the specified period of time, mortality in % is determined. 100% means all caterpillars have been killed and 0% means none of the caterpillars have been killed. The mortality values determined thus are recalculated using the Colby-formula (see sheet 1).
[0117] According to the present application in this test e.g. the following combinations show a synergistic effect in comparison to the single compounds:
Table A: Spodoptera frugiperda - spray test
Figure imgf000071_0001
obs. = observed insecticidal efficacy, ** cal. = efficacy calculated with Colby-formula
Example B
Phaedon cochleariae - spray test
Solvent: 7 parts by weight of dimethylformamide
Emulsifier: alkylaryl polyglycol ether
[0118] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and is diluted with water, containing an emulgator concentration of 1 OOOppm, to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water. Ammonium salt and/or penetration enhancer in a dosage of 1 OOOppm are added to the desired concentration if necessary.
[0119] Cabbage leaves (Brassica oleraced) are treated by being sprayed with the preparation of the active compound of the desired concentration and are infested with mustard beetle larvae {Phaedon cochleariae).
[0120] After the specified period of time mortality in % is determined. 100 % means all the beetle larvae have been killed and 0 % means none of the beetle larvae have been killed. The mortality values determined thus are recalculated using the Colby-formula (see sheet 1).
[0121] According to the present application in this test e.g. the following combinations show a synergistic effect in comparison to the single compounds:
Table B-l; Phaedon cochleariae - spray test
Figure imgf000073_0001
obs. = observed insecticidal efficacy, ** cal. = efficacy calculated with Colby-formula

Claims

Patent claims:
1. Active compound combinations comprising at least one compound of the formula (1-1)
Figure imgf000074_0001
wherein
Hal represents F, CI, I or Br; and
X' represents Ci-Ce alkyl or substituted Ci-Ce alkyl having at least one substituent selected from the group consisting of halogen, hydroxy, cyano, nitro, amino, halo C1-C3 alkyl group, preferably Ci-Cehaloalkyl;
A' represents C1-C3 alkyl, C1-C3 haloalkyl, halogen; n represents 0, 1, 2, 3 or 4, preferably 0, 1 or 2; and at least one active compound selected from groups (2) to (24) below:
Group (2) Strobilurins of the general formula (II)
Figure imgf000074_0002
in which
A represents one of the groups
Figure imgf000074_0003
2
A" represents NH represents N or CH, represents one of the
Figure imgf000075_0001
where the bond marked with an asterisk (*) is attached to the phenyl ring, represents phenyl, phenoxy or pyridinyl, each of which is optionally mono- or disubstituted by identical or different substituents from the group consisting of chlorine, cyano, methyl and trifluoromethyl, or represents 1 -(4-chlorophenyl)- pyrazol-3-yl or represents l,2-propanedione-bis(0-methyloxime)-l-yl, represents hydrogen or fluorine;
Group (3) Triazoles of the general formula (III)
Figure imgf000075_0002
in which
Q represents hydrogen or SH, m represents 0 or 1 ,
R13 represents hydrogen, fluorine, chlorine, phenyl or 4-chlorophenoxy, R14 represents hydrogen or chlorine,
A4 represents a direct bond, -CH2-, -(CH2)2-, -0-, represents *-CH2-CHR17- CH=CR17-, where the bond marked with * is attached to the phenyl ring, in case
R15 and R17 together represent -CH2-CH2-CH[CH(CH3)2]- or -CH2-CH2-C(CH3)2-, A5 represents C or Si (silicon),
A4 further represents -N(R17)- and A5 furthermore together with R15 and R16 represents the group C=N-R18, in which case R17 and R18 together represent the group
, where the bond marked with * is attached to R ,
Figure imgf000076_0001
represents hydrogen, hydroxyl or cyano, represents 1 -cyclopropylethyl, 1 -chlorocyclopropyl, Ci-C i-alkyl, Ci-Ce- hydroxyalkyl, Ci-C i-alkylcarbonyl, Ci-C2-haloalkoxy-Ci-C2-alkyl, trimethylsilyl- Ci-C2-alkyl, monofluorophenyl or phenyl, and R16 furthermore together represent -0-CH2-CH(R18)-0-, -0-CH2-CH(R18)-CH2-, or -0-CH-(2-chlorophenyl)-, represents hydrogen, Ci-C4-alkyl or bromine;
Group (4) Sulphenamides of the general formula (IV)
Figure imgf000076_0002
in which R represents hydrogen or methyl;
Group (5) Valinamides selected from
(5-1) iprovalicarb
(5-2) N1-[2-(4- {[3-(4-chlorophenyl)-2-propynyl]oxy} -3-methoxyphenyl)ethyl]-N2- (methylsulphonyl)-D-valinamide
(5-3) benthiavalicarb Group (6) Carboxamides of the general formula (V)
Figure imgf000077_0001
in which
X represents 2-chloro-3-pyridinyl, represents 1 -methylpyrazol-4-yl which is substituted in the 3-position by methyl or trifluoromethyl and in the 5-position by hydrogen or chlorine, represents 4-ethyl-2-ethylamino-l ,3-thiazol-5-yl, represents 1 -methyl-cyclohexyl, represents 2,2-dichloro-l -ethyl-3-methylcyclopropyl, represents 2-fluoro-2-propyl, 3,4-dichloroisothiazol-5-yl, 5,6-dihydro-2-methyl- 1 ,4-oxathiin-3-yl, 4-methyl-l ,2,3-thiadiazol-5-yl, 4,5-dimethyl-2- trimethylsilylthiophen-3-yl, l -methylpyrrol-3-yl which is substituted in the 4-position by methyl or trifluoromethyl and in the 5-position by hydrogen or chlorine, or represents phenyl which is mono- to trisubstituted by identical or different substituents from the group consisting of chlorine, methyl or trifluoromethyl,
Y represents a direct bond, Ci-C6-alkanediyl (alkyl) which is optionally substituted by chlorine, cyano or oxo, represents C2-C6-alkenediyl (alkenylene) or thiophenediyl, represents hydrogen, Ci-C6-alkyl or the group
Figure imgf000077_0002
represents CH or N,
R20 represents hydrogen, chlorine, cyano, Ci-C6-alkyl, phenyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of chlorine and di(Ci-C3-alkyl)aminocarbonyl,
R represents hydrogen, chlorine or isopropoxy, represents hydrogen, chlorine, hydroxyl, methyl, trifluoromethyl or di(Ci-C3- alkyl)aminocarbonyl, and R furthermore together represent *-CH(CH3)-CH2-C(CH3)2- *-CH(CH3)-0-C(CH3)2- where the bond marked with * is attached to R20;
Group (7) Dithiocarbamates selected from
(7-1 mancozeb
(7-2 maneb
(7-3 metiram
(7-4 propineb
(7-5 thiram
(7-6 zineb
(7-7 ziram
Group (8) Acylalanines of the general formula (VI)
Figure imgf000078_0001
in which marks a carbon atom in the R or the S configuration, preferably in the configuration,
R represents benzyl, furyl or methoxymethyl;
Group (9): Anilinopyrimidines of the general formula (VII)
Figure imgf000078_0002
in which
R24 represents methyl, cyclopropyl or 1 -propynyl; Group (10): Benzimidazoles of the general formula (VIII)
Figure imgf000079_0001
in which
R25 and R26 each represent hydrogen or together represent -O-CF2-O-, R27 represents hydrogen, Ci-C4-alkylaminocarbonyl or represents dimethylisoxazol-4-ylsulphonyl,
R28 represents chlorine, methoxycarbonylamino, chlorophenyl, furyl or thiazolyl;
Group (11): Carbamates of the general formula (IX)
Figure imgf000079_0002
in which
R29 represents n- or isopropyl,
R30 represents di(Ci-C2-alkyl)amino-C2-C4-alkyl or diethoxyphenyl, salts of these compounds also being included; Group (12): Dicarboximides selected from
(12-1) captafol
(12-2) captan
(12-3) folpet
(12-4) iprodione
(12-5) procymidone
(12-6) vinclozolin
Group (13): Guanidines selected from
(13-1) dodine (13-2) guazatine
(13-3) iminoctadine triacetate
(13-4) iminoctadine tris(albesilate)
Group (14): Imidazoles selected from
(14-1) cyazofamid
(14-2) prochloraz
(14-3) triazoxide
(14-4) pefurazoate
Group (15): Morpholines of the general formula (X)
Figure imgf000080_0001
in which
R31 and R32 independently of one another represent hydrogen or methyl,
R33 represents Ci-Ci4-alkyl (preferably Ci2-Ci4-alkyl), Cs-Cn-cycloalkyl (preferably Cio-Ci2-cycloalkyl), phenyl-Ci-C4-alkyl, which may be substituted in the phenyl moiety by halogen or Ci-C4-alkyl or represents acrylyl which is substituted by chlorophenyl and dimethoxyphenyl;
Group (16): Pyrroles of the general formula (XI)
Figure imgf000080_0002
in which R34 represents chlorine or cyano,
R35 represents chlorine or nitro, R36 represents chlorine, R35 and R36 furthermore together represent -O-CF2-O-;
Group (17): (Thio)phosphonates selected from
(17-1) fosetyl-Al
(17-2) phosphonic acid,
(17-3) tolclophos-methyl;
Group ( 18): Phenylethanamides of the general formula (XII)
Figure imgf000081_0001
in which
R37 represents unsubstituted or fluorine-, chlorine-, bromine-, methyl- or substituted phenyl, 2-naphthyl, 1 ,2,3,4-tetrahydronaphthyl or indanyl;
Group ( 19): Fungicides selected from
(19-1) acibenzolar-S-methyl
(19-2) chlorothalonil
(19-3) cymoxanil
(19-4) edifenphos
(19-5) famoxadone
(19-6) fluazinam
(19-7) copper oxychloride
(19-8) copper hydroxide
(19-9) oxadixyl
(19-10) spiroxamine
(19-l l) dithianon
(19-12) metrafenone
(19-14) 2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one
(19-15) probenazole
(19-16) isoprothiolane
(19-17) kasugamycin
(19-18) phthalide
(19-19) ferimzone (19-20) tricyclazole
(19-21) cyprosulfamide
(19-22) mandipropamid
Group (20): (Thio)urea derivatives selected from
(20-1) pencycuron
(20-2) thiophanate-methyl
(20-3) thiophanate- ethyl
Group (21): Amides of the general formula (XIII)
Figure imgf000082_0001
in which
A7 represents a direct bond or -0-,
A8 represents -C(=0)NH- or -NHC(=0)-,
R38 represents hydrogen or Ci-C i-alkyl,
R39 represents Ci-C6-alkyl; Group (22): Triazolopyrimidines of the general formula (XIV)
Figure imgf000082_0002
in which
R40 represents Ci-C6-alkyl or C2-C6-alkenyl,
R41 represents Ci-C6-alkyl, R40 and R41 furthermore together represent C4-Cs-alkanediyl (alkyl) which is mono- or disubstituted by Ci-C6-alkyl, R42 represents bromine or chlorine,
R43 and R47 independently of one another represent hydrogen, fluorine, chlorine or methyl, R44 and R46 independently of one another represent hydrogen or fluorine, R45 represents hydrogen, fluorine or methyl,
Group (23): Iodochromones of the general formula (XV)
Figure imgf000083_0001
in which
R48 represents Ci-C6-alkyl,
R49 represents Ci-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl; Group (24): Biphenylcarboxamides of the general formula (XVI)
Figure imgf000083_0002
in which
R50 represents hydrogen or fluorine,
R51 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, trifluoromethoxy, -CH=N-OMe or -C(Me)=N-OMe,
R52 represents hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl,
Het represents one of the radicals Hetl to Het7 below:
Figure imgf000084_0001
R53 represents iodine, methyl, difluoromethyl or trifluoromethyl, R54
represents hydrogen, fluorine, chlorine or methyl, R55 represents methyl, difluoromethyl or trifluoromethyl,
R56 represents chlorine, bromine, iodine, methyl, difluoromethyl or trifluoromethyl, R57 represents methyl or trifluoromethyl.
Composition according to Claim 1 , comprising the compound of the formula (1-1) and at least one of the compounds from the list below
azoxystrobin
fluoxastrobin
(2£')-2-(2- {[6-(3-chloro-2-methylphenoxy)-5-fluoro-4-pyrimidinyl]oxy}phenyl)-2- (methoxyimino)-N-methylethanamide
trifloxystrobin
(2£)-2-(methoxyimino)-N-methyl-2-(2- {[( {(l£)-l -[3-(trifluoromethyl)- phenyl]ethylidene} amino)oxy]methyl}phenyl)ethanamide
(2£')-2-(methoxyimino)-N-methyl-2- {2-[(E)-( { 1 -[3-(trifluoromethyl)phenyl]- ethoxy} imino)methyl]phenyl} ethanamide
orysastrobin
5-methoxy-2-methyl-4-(2- {[( {(l£')-l -[3-(trifluoromethyl)phenyl]ethylidene} - amino)oxy]methyl}phenyl)-2,4-dihydro-3H-l ,2,4-triazol-3-one
kresoxim-methyl
dimoxystrobin
picoxystrobin
pyraclostrobin metominostrobin
azaconazole
etaconazole
propiconazole
- difenoconazole
bromuconazole
cyproconazole
hexaconazole
penconazole
- myclobutanil
tetraconazole
flutriafol
epoxiconazole
flusilazole
- simeconazole
prothioconazole
fenbuconazole
tebuconazole
ipconazole
- metconazole
triticonazole
bitertanol
triadimenol
triadimefon
- fluquinconazole
quinconazole
dichlofluanid
tolylfluanid
iprovalicarb
- benthiavalicarb
2-chloro-N-(l ,l,3-trimethylindan-4-yl)nicotinamide
boscalid
furametpyr
N-(3 -p-tolylthiophen-2-yl)- 1 -methyl-3 -trifluoromethyl- 1 H-pyrazole-4- carboxamide
ethaboxam
fenhexamid carpropamid
2-chloro-4-(2-fluoro-2-methylpropionylamino)-N,N-dimethylbenzamide fluopicolid
zoxamide
- 3,4-dichloro-N-(2-cyanophenyl)isothiazole-5-carboxamide
carboxin
tiadinil
penthiopyrad
silthiofam
- N-[2-(l,3-dimethylbutyl)phenyl]-l-methyl-4-(trifluoromethyl)-lH-pyrrole-3- carboxamide
flutolanil
N-[2-(l ,3-dimethylbutyl)phenyl]-5-fluoro- 1 ,3-dimethyl-l H-pyrazole-4-carboxamide N- {2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl} -2-(trifluoromethyl)benzamide - mancozeb having the IUPAC name manganese ethylenebis(dithiocarbamate)
(polymeric) complex with zinc salt
maneb
metiram having the IUPAC name zinc ammoniate ethylenebis(dithiocarbamate)- poly(ethylenethiuram disulphide)
- propineb
thiram
zineb
ziram
benalaxyl
- furalaxyl
metalaxyl
metalaxyl-M
benalaxyl-M
cyprodinil
- mepanipyrim
pyrimethanil
6-chloro-5-[(3,5-dimethylisoxazol-4-yl)sulphonyl]-2,2-difluoro-5H-
[l,3]dioxolo[4,5-f]benzimidazole
benomyl
- carbendazim
chlorfenazole
fuberidazole thiabendazole
diethofencarb
propamocarb
propamocarb-hydrochloride
propamocarb-fosetyl
captafol
captan
folpet
iprodione
procymidone
vinclozolin
dodine
guazatine
iminoctadine triacetate
cyazofamid
prochloraz
triazoxide
pefurazoate
aldimorph
tridemorph
dodemorph
fenpropimorph
dimethomorph
fenpiclonil
fludioxonil
pyrrolnitrin
fosetyl-Al
phosphonic acid
tolclofos-methyl
2-(2,3-dihydro-lH-inden-5-yl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2- (methoxyimino)acetamide
N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(methoxyimino)-2-(5,6,7,8-tetrahydro- naphthalen-2-yl)acetamide
2-(4-chlorophenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(methoxyimino)acetamide
2-(4-bromophenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-
(methoxyimino)acetamide 2-(4-methylphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(methoxyimino)- acetamide
2-(4-ethylphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(methoxyimino)acetamide acibenzolar-S-methyl
chlorothalonil
cymoxanil
edifenphos
famoxadone
fluazinam
copper oxychloride
oxadixyl
spiroxamine
dithianon
metrafenone
2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one
probenazole
isoprothiolane
kasugamycin
phthalide
ferimzone
tricyclazole
N-({4-[(cyclopropylamino)carbonyl]phenyl}sulphonyl)-2-methoxybenzamide
2-(4-chlorophenyl)-N- {2-[3-methoxy-4-(prop-2-yn-l -yloxy)phenyl] ethyl} -2-(prop-
2-yn- 1 -yloxy) acetamide
pencycuron
thiophanate-methyl
thiophanate- ethyl
fenoxanil
diclocymet
5-chloro-N-[(7S 2,2,2-trifluoro-l-methylethyl]-6-(2,4,6-trifluoro- phenyl)[l ,2,4]triazolo[l ,5-a]pyrimidine-7-amine
5-chloro-N-[(^ Rj-l,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[l,2,4]triazolo- [1 ,5-a]pyrimidine-7-amine
5-chloro-6-(2-chloro-6-fluorophenyl)-7-(4-methylpiperidin-l-yl)[l,2,4]triazolo- [l,5-a]pyrimidine
5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-methylpiperidin-l-yl)[l,2,4]triazolo- [l,5-a]pyrimidine 2-butoxy-6-iodo-3-propylbenzopyran-4-one
2-ethoxy-6-iodo-3-propylbenzopyran-4-one
6-iodo-2-propoxy-3-propylbenzopyran-4-one
2-but-2-ynyloxy-6-iodo-3-propylbenzopyran-4-one
- 6-iodo-2-(l -methylbutoxy)-3-propylbenzopyran-4-one
2- but-3-enyloxy-6-iodobenzopyran-4-one
3- butyl-6-iodo-2-isopropoxybenzopyran-4-one
N-(3',4'-dichloro-5-fluoro- 1 , 1 '-biphenyl-2-yl)-3-(difluoromethyl)- 1 -methyl- 1H- pyrazole-4-carboxamide
- 3-(difluoromethyl)-N- {3'-fluoro-4'-[(£')-(methoxyimino)methyl]-l , 1 '-biphenyl-2- yl} - 1 -methyl- lH-pyrazole-4-carboxamide
3- (trifluoromethyl)-N- {3'-fluoro-4'-[(£)-(methoxyirnino)methyl]-l, -biphenyl-2- yl} - 1 -methyl- lH-pyrazole-4-carboxamide
N-(3',4'-dichloro- 1 , 1 '-biphenyl-2-yl)-5-fluoro- 1 ,3-dimethyl- lH-pyrazole-4- carboxamide
N-(4'-chloro-3'-fiuoro- 1 , 1 '-biphenyl-2-yl)-2-methyl-4-(trifluoromethyl)- 1,3- thiazole-5-carboxamide
N-(4'-chloro- 1 , 1 '-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl- 1 ,3-thiazole-5- carboxamide
- N-(4'-bromo- 1 , 1 '-biphenyl-2-yl)-4-(difluoromethyl)-2-methyl- 1 ,3-thiazole-5- carboxamide
4- (difluoromethyl)-2-methyl-N- [4'-(trifluoromethyl)- 1 , 1 '-biphenyl-2-yl] -1,3- thiazole-5-carboxamide.
3. Use of active compound combinations as defined in Claim 1 or Claim 2 for controlling animal pests.
4. Method for controlling animal pests, characterized in that active compound combinations as defined in Claim 1 or Claim 2 are allowed to act on animal pests and/or their habitat and/or seed.
Method according to Claim 4, characterized in that an active compound of the formula (I- 1) and one of the active compounds of group (2) to (24) are allowed to act simultaneously on seed.
6. Method according to Claim 4, characterized in that an active compound of the formula I and one of the active compounds of group (2) to (24) are allowed to act at different times on seed.
7. Process for preparing insecticidal and acaricidal compositions, characterized in that active compound combinations as defined in Claim 1 or Claim 2 are mixed with extenders and/or surfactants.
8 Use of an active compound combination according to Claim 1 or Claim 2 for treating seed.
9. Use of active compound combinations according to Claim 1 or Claim 2 for treating transgenic plants.
10. Use of active compound combinations according to Claim 1 or Claim 2 for treating seed of transgenic plants.
11. Seed treated with an active compound combination according to Claim 1 or Claim 2.
12. Seed according to Claim 11 which has been treated simultaneously with an active compound of the formula I and one of the active compounds of group (2) to (24).
13. Seed wherein a compound of formula (1-1) according to claim 1 and an active compound of group (2) to (24) according to claim 1 are present in one or different layers on the seed, a coating or as a further layer or further layers in addition to a coating.
PCT/EP2014/057687 2013-04-19 2014-04-16 Insecticidal and/or fungicidal synergistic combinations of phthaldiamide derivatives and a further active ingredient WO2014170354A1 (en)

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EP13164451.0 2013-04-19

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0919542A2 (en) * 1997-11-25 1999-06-02 Nihon Nohyaku Co., Ltd. Phthalic acid diamide derivatives, agricultural and horticultural insecticides, and a method for application of the insecticides
WO2004080181A1 (en) * 2003-03-13 2004-09-23 Bayer Cropscience Aktiengesellschaft Synergistic active substance combinations
WO2007101547A2 (en) * 2006-03-06 2007-09-13 Bayer Cropscience Ag Synergistic combinations of active ingredients
WO2012034472A1 (en) * 2010-09-13 2012-03-22 中化蓝天集团有限公司 Cyano benzenedicarboxamide compounds, preparing methods and as agricultural insecticides uses thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0919542A2 (en) * 1997-11-25 1999-06-02 Nihon Nohyaku Co., Ltd. Phthalic acid diamide derivatives, agricultural and horticultural insecticides, and a method for application of the insecticides
WO2004080181A1 (en) * 2003-03-13 2004-09-23 Bayer Cropscience Aktiengesellschaft Synergistic active substance combinations
WO2007101547A2 (en) * 2006-03-06 2007-09-13 Bayer Cropscience Ag Synergistic combinations of active ingredients
WO2012034472A1 (en) * 2010-09-13 2012-03-22 中化蓝天集团有限公司 Cyano benzenedicarboxamide compounds, preparing methods and as agricultural insecticides uses thereof

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