Patent Application
20100222218
The present invention relates to the use of heterocyclic carboxylic acid derivatives of the formula (I) below
in which the symbols have the meanings given in the description, or to their agrochemically active salts or to mixtures of these compounds and/or their agrochemically active salts with other active compounds for controlling animal pests and/or phytopathogenic harmful fungi, to methods and compositions for controlling animal pests and/or phytopathogenic harmful fungi in and/or on plants or in and/or on seed of plants, to processes for preparing such compositions and to treated seed.
The present invention furthermore relates to heterocyclic carboxylic acid derivatives of the formula (I), to processes for their preparation and to their use for controlling pests in agriculture, horticulture and forestry, in the protection of materials and also in the domestic and hygiene field.
The present invention also relates to enhancing the activity of crop protection compositions comprising insecticidal heterocyclic carboxylic acid derivatives of the formula (I) by addition of ammonium or phosphonium salts and, if appropriate, penetrants, to the corresponding compositions, to processes for their preparation and to their use in crop protection, in particular as insecticides and/or acaricides.
It is already known that certain pyrazolopyrimidine derivatives have fungicidal properties, see, for example, WO 04/000844, WO 05/082907 and WO 06/087120. Furthermore, it is already known that certain pyrazolopyrimidine derivatives have insecticidal properties, see, for example, WO 04/000844.
However, since the environmental and economic requirements imposed on modern-day pesticides are continually increasing, with regard, for example, to the spectrum of action, toxicity, selectivity, application rate, formation of residues, and favourable preparability, and since, furthermore, there may be problems, for example, with resistances, a constant task is to develop novel pesticides which in some areas at least have advantages over their known counterparts.
This invention now provides novel heterocyclic carboxylic acid derivatives of the formula (I)
in which the symbols have the following meaning:
or represents a bond,
where the dashed bonds may be single bonds, double bonds or aromatic bonds;
Heterocyclic carboxylic acid derivatives of the formula (I) according to the invention and their agrochemically active salts are highly suitable for use as pesticides, in particular for controlling animal pests, such as insects, parasites of the sub-class of the Acari (Acarina) (such as mites, spider mites and/or ticks) and/or nematodes. The compounds according to the invention mentioned above show in particular strong insecticidal and/or acaricidal and/or nematicidal activity and can be used both in crop protection, in the domestic and hygiene field and in the protection of materials.
The compounds of the formula (I) may be present either in pure form or as mixtures of various possible isomeric forms, in particular of stereoisomers,such as E and Z, threo and erythro, and also optical isomers, such as R and S isomers or atropisomers, and, if appropriate, also of tautomers. The invention comprises both the pure isomers and mixtures thereof.
If appropriate, the compounds of the formula (I) may be present in various polymorphic forms or as mixtures of differing polymorphic forms. Both the pure polymorphs and the polymorph mixtures are provided by the invention and can be used according to the invention.
Depending on the nature of the substituents defined above, the compounds of the formula (I) have acidic or basic properties and may form salts, if appropriate also inner salts. If the compounds of the formula (I) carry hydroxyl groups, carboxyl groups or other groups which induce acidic properties, these compounds can be converted with bases into salts. Suitable bases are, for example, hydroxides, carbonates, bicarbonates of the alkali metals and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, furthermore ammonia, primary, secondary and tertiary amines having (C1-C4)-alkyl radicals, mono-, di- and trialkanolamines of (C1-C4)-alkanols, choline and also chlorocholine. If the compounds of the formula (I) carry amino groups, alkylamino groups or other groups which induce basic properties, these compounds can be converted with acids into salts. Suitable acids are, for example, mineral acids, such as hydrochloric acid, sulphuric acid and phosphoric acid, organic acids, such as acetic acid or oxalic acid, and acidic salts, such as NaHSO4 and KHSO4. The salts obtainable in this manner also have insecticidal properties.
The formula (I) provides a general definition of the compounds according to the invention, i.e. the heterocyclic carboxylic acid derivatives.
Accordingly, the present invention relates to
in which
or represents a bond,
where the dashed bonds may be single bonds, double bonds or aromatic bonds;
Hereinbelow, preferred substituents, fragments or ranges of the radicals listed in the formulae mentioned above and below are illustrated for a preferred embodiment of the present invention:
or represents a bond,
where the dashed bonds may be single bonds, double bonds or aromatic bonds;
halogen, cyano, nitro, amino, hydroxyl, formyl, carboxy, carboxyalkyl, carbamoyl, thiocarbamoyl;
in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms;
in each case straight-chain or branched alkenyl, alkynyl, alkynyloxy or alkenyloxy having in each case 2 to 6 carbon atoms;
in each case straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulphinyl or haloalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
in each case straight-chain or branched haloalkenyl or haloalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;
in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties;
cycloalkyl having 3 to 8 carbon atoms which is optionally mono- or disubstituted by fluorine, chlorine, C1-C3-alkyl or C1-C3-alkoxy;
2,3- or 3,4-attached 1,3-propanediyl, 1,4-butanediyl, methylenedioxy (—O—CH2—O—) or 1,2-ethylenedioxy (—O—CH2—CH2—O—), where these radicals may be mono- or polysubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms and haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms; or
The formula (I) provides a general definition of the compounds according to the invention. Hereinbelow, particularly preferred substituents, fragments or ranges of the radicals listed in the formulae mentioned above and below are illustrated for a particularly preferred embodiment of the present invention:
or represents a bond,
where the dashed bonds may be single bonds, double bonds or aromatic bonds;
The formula (I) provides a general definition of the compounds according to the invention. Hereinbelow, very particularly preferred substituents, fragments or ranges of the radicals listed in the formulae mentioned above and below are illustrated for a very particularly preferred embodiment of the present invention; very particular preference is given here to the compounds of the formulae (I-1) to (I-3) which correspond to the formula (I), where the symbols A, B1, B2, B3 and B4 have the following very particularly preferred meanings:
For formula (I-1),
for formula (I-2)
and B3 is a bond;
for formula (I-3),
and B3 is a bond;
The other symbols in the formulae (I-1) to (I-3) have the very particularly preferred meanings below:
The formula (I) provides a general definition of the compounds according to the invention. Hereinbelow, especially very particularly preferred substituents, fragments or ranges of the radicals listed in the formulae mentioned above and below are illustrated for an especially very particularly preferred embodiment of the present invention; special very particular preference is given here to the compounds of the formula (I-3) which correspond to the formula (I), where the symbols A, B1, B2, B3 and B4 have the following especially very particularly preferred meanings:
For formula (I-3),
and B3 is a bond.
The other symbols in the formula (I-3) have the especially very particularly preferred meanings below:
The general or preferred radical definitions or illustrations listed above can be combined with one another as desired, i.e. including combinations between the respective ranges and preferred ranges. They apply to the end products and, correspondingly, to precursors and intermediates.
Preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being preferred (preferable).
Particular preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred.
Very particular preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being very particularly preferred.
Special particular preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being especially particularly preferred.
Special very particular preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being especially very particularly preferred.
Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, can in each case be straight-chain or branched as far as this is possible, including in combination with heteroatoms, such as, for example, in alkoxy.
Unless indicated otherwise, optionally substituted radicals may be mono- or polysubstituted, where in the case of polysubstitution the substituents can be identical or different.
In the literature it has already been described how the action of various active compounds can be boosted by addition of ammonium salts. The salts in question, however, are detersive salts (for example WO 95/017817) or salts which have relatively long alkyl substituents and/or aryl substituents and which have a permeabilizing action or which increase the active compound's solubility (for example EP-A 0 453 086, EP-A 0 664 081, FR-A 2 600 494, U.S. Pat. No. 4,844,734, U.S. Pat. No. 5,462,912, U.S. Pat. No. 5,538,937, US-A 03/0224939, US-A 05/0009880, US-A 05/0096386). Moreover, the prior art describes the action only for particular active compounds and/or particular applications of the corresponding compositions. In other cases, they are salts of sulphonic acids where the acids for their part have paralysing action on the insects (U.S. Pat. No. 2,842,476). A boost of action by ammonium sulphate, for example, is described by way of example for the herbicides glyphosate and phosphinothricin (U.S. Pat. No. 6,645,914, EP-A2 0 036 106). However, this prior art neither discloses nor suggests a corresponding action for insecticides.
The use of ammonium sulphate as formulating assistant has also been described for certain active compounds and applications (WO 92/16108), but its purpose therein is to stabilize the formulation, not to boost the action.
It has now been found, entirely surprisingly, that the action of insecticides and/or acaricides from the class of the heterocyclic carboxylic acid derivatives (I) can be boosted significantly through the addition of ammonium salts or phosphonium salts to the application solution or through the incorporation of these salts into a formulation comprising heterocyclic carboxylic acid derivatives (I). The present invention therefore provides for the use of ammonium salts or phosphonium salts for boosting the action of crop protection compositions which comprise as their active compound insecticidal and/or acaricidal heterocyclic carboxylic acid derivatives (I). The invention likewise provides compositions which comprise insecticidal and/or acaricidal heterocyclic carboxylic acid derivatives (I) and action-boosting ammonium salts or phosphonium salts, including not only formulated active compounds but also ready-to-use compositions (spray liquors). The invention further provides, finally, for the use of these compositions for controlling harmful insects and/or spider mites.
Ammonium salts and phosphonium salts which inventively boost the activity of crop protection compositions comprising heterocyclic carboxylic acid derivatives (I) are defined by formula (II)
in which
The ammonium salts and phosphonium salts of the formula (II) can be used in a broad concentration range to boost the activity of crop protection compositions comprising heterocyclic carboxylic acid derivatives (I). In general the ammonium salts or phosphonium salts are used in the ready-to-use crop protection composition in a concentration of 0.5 to 80 mmol/l, preferably 0.75 to 37.5 mmol/1, more preferably 1.5 to 25 mmol/l. In the case of a formulated product the ammonium salt and/or phosphonium salt concentration in the formulation is chosen such that it is within these stated general, preferred or particularly preferred ranges after the formulation has been diluted to the desired active-ingredient concentration. The concentration of the salt in the formulation is typically 1%-50% by weight.
In one preferred embodiment of the invention the activity is boosted by adding to the crop protection compositions not only an ammonium salt and/or phosphonium salt but also, additionally, a penetrant. It is considered entirely surprising that even in these cases an even greater boost to activity is observed. The present invention therefore likewise provides for the use of a combination of penetrant and ammonium salts and/or phosphonium salts to boost the activity of crop protection compositions which comprise insecticidal and/or acaricidal heterocyclic carboxylic acid derivatives (I) as active compound. The invention likewise provides compositions which comprise insecticidal and/or acaricidal heterocyclic carboxylic acid derivatives (I), penetrants and ammonium salts and/or phosphonium salts, including specifically not only formulated active compounds but also ready-to-use compositions (spray liquors). The invention additionally provides, finally, for the use of these compositions for controlling harmful insects.
Suitable penetrants in the present context include all those substances which are typically used to enhance the penetration of active agrochemical compounds into plants. Penetrants are defined in this context by their ability to penetrate from the aqueous spray liquor and/or from the spray coating into the cuticle of the plant and thereby to increase the mobility of active compounds in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used in order to determine this property.
Examples of suitable penetrants include alkanol alkoxylates. Penetrants of the invention are alkanol alkoxylates of the formula
R—O—(-AO)v—R′ (III)
in which
One preferred group of penetrants are alkanol alkoxylates of the formula
R—O—(-EO—)n—R′ (III-a)
in which
A further preferred group of penetrants are alkanol alkoxylates of the formula
R—O—(-EO—)p—(—PO—)q—R′ (III-b)
in which
A further preferred group of penetrants are alkanol alkoxylates of the formula
R—O—(—PO—)r-(EO—)s—R′ (III-c)
in which
A further preferred group of penetrants are alkanol alkoxylates of the formula
R—O—(-EO—)p—(—BO—)q—R′ (III-d)
in which
A further preferred group of penetrants are alkanol alkoxylates of the formula
R—O—(—BO—)4—(-EO—)s—R′ (III-e)
in which
A further preferred group of penetrants are alkanol alkoxylates of the formula
CH3—(CH2)t—CH2—O—(—CH2—CH2—O—)u—R′ (III-f)
in which
In the formulae indicated above,
R preferably represents butyl, isobutyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-octyl, isooctyl, 2-ethylhexyl, nonyl, isononyl, decyl, n-dodecyl, isododecyl, lauryl, myristyl, isotridecyl, trimethylnonyl, palmityl, stearyl or eicosyl.
As an example of an alkanol alkoxylate of the formula (III-c) mention may be made of 2-ethylhexyl alkoxylate of the formula
in which
and the numbers 8 and 6 represent average values.
As an example of an alkanol alkoxylate of the formula (III-d) mention may be made of the formula
CH3—(CH2)10—O—(-EO—)6—(—BO—)2—CH3 (III-d-1)
in welcher
and the numbers 10, 6 and 2 represent average values.
Particularly preferred alkanol alkoxylates of the formula (III-f) are compounds of this formula in which
Mention may be made with very particular preference of alkanol alkoxylate of the formula (III-f-1)
CH3—(CH2)t—CH2—O—(—CH2—CH2—O—)u—H (III-f-1)
in which
A general definition of the alkanol alkoxylates is given by the formulae above. These substances are mixtures of compounds of the stated type with different chain lengths. The indices therefore have average values which may also deviate from whole numbers.
The alkanol alkoxylates of the formulae stated are known and in some cases are available commercially or can be prepared by known methods (cf. WO 98/35 553, WO 00/35 278 and EP-A 0 681 865).
Suitable penetrants also include, for example, substances which promote the availability of the compounds of the formula (I) in the spray coating. These include, for example, mineral or vegetable oils. Suitable oils are all mineral or vegetable oils—modified or otherwise—which can typically be used in agrochemical compositions. Mention may be made by way of example of sunflower oil, rapeseed oil, olive oil, castor oil, colza oil, maize seed oil, cotton seed oil and soybean oil, or the esters of said oils. Preference is given to rapeseed oil, sunflower oil and their methyl or ethyl esters.
The concentration of penetrant in the compositions according to invention can be varied within a wide range. In the case of a formulated crop protection composition it is in general 1% to 95%, preferably 1% to 55%, more preferably 15%-40% by weight. In the ready-to-use compositions (spray liquors) the concentrations are generally between 0.1 and 10 g/l, preferably between 0.5 and 5 g/l.
Crop protection compositions according to invention may also comprise further components, examples being surfactants and/or dispersing assistants or emulsifiers.
Suitable nonionic surfactants and/or dispersing assistants include all substances of this type that can typically be used in agrochemical compositions. Preferably mention may be made of polyethylene oxide-polypropylene oxide block copolymers, polyethylene glycol ethers of linear alcohols, reaction products of fatty acids with ethylene oxide and/or propylene oxide, and also polyvinyl alcohol, polyvinylpyrrolidone, copolymers of polyvinyl alcohol and polyvinylpyrrolidone, and copolymers of (meth)acrylic acid and (meth)acrylic esters, and additionally alkyl ethoxylates and alkylaryl ethoxylates, which optionally may be phosphated and optionally may be neutralized with bases, mention being made, by way of example, of sorbitol ethoxylates, and, as well, polyoxyalkylenamine derivatives.
Suitable anionic surfactants include all substances of this type that can typically be used in agrochemical compositions. Preference is given to alkali metal salts and alkaline earth metal salts of alkylsulphonic acids or alkylarylsulphonic acids.
A further preferred group of anionic surfactants and/or dispersing assistants are the following salts that are of low solubility in plant oil: salts of polystyrenesulphonic acids, salts of polyvinylsulphonic acids, salts of naphthalenesulphonic acid-formaldehyde condensation products, salts of condensation products of naphthalenesulphonic acid, phenolsulphonic acid and formaldehyde, and salts of lignosulphonic acid.
Suitable additives which may be included in the formulations according to invention are emulsifiers, foam inhibitors, preservatives, antioxidants, colorants and inert filling materials.
Preferred emulsifiers are ethoxylated nonylphenols, reaction products of alkylphenols with ethylene oxide and/or propylene oxide, ethoxylated arylalkylphenols, and also ethoxylated and propoxylated arylalkylphenols, and also sulphated or phosphated arylalkyl ethoxylates and/or arylalkyl ethoxypropoxylates, mention being made by way of example of sorbitan derivatives, such as polyethylene oxide-sorbitan fatty acid esters, and sorbitan fatty acid esters.
The active compounds 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:
From the order of the Anoplura (Phthiraptera), for example, Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.
From the class of the Arachnida, for example, Acarus siro, Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici.
From the class of the Bivalva, for example, Dreissena spp.
From the order of the Chilopoda, for example, Geophilus spp., Scutigera spp.
From the order of the Coleoptera, for example, Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp., Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus, Bruchus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica, Curculio spp., Cryptorhynchus lapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinus cubae, Gibbium psylloides, heteronychus arator, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosterna consanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Popillia japonica, Premnotrypes spp., Psylliodes chrysocephala, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Sternechus spp., Symphyletes spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp.
From the order of the Collembola, for example, Onychiurus armatus.
From the order of the Dermaptera, for example, Forficula auricularia.
From the order of the Diplopoda, for example, Blaniulus guttulatus.
From the order of the Diptera, for example, Aedes spp., Anopheles spp., Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata, Chrysomyia spp., Cochliomyia spp., Cordylobia anthropophaga, Culex spp., Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila spp., Fannia spp., Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza spp., Lucilia spp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp., Tabanus spp., Tannia spp., Tipula paludosa, Wohlfahrtia spp.
From the class of the Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.
From the class of the helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp., Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti.
It is furthermore possible to control protozoa, such as Eimeria.
From the order of the heteroptera, for example, Anasa tristis, Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Psallus seriatus, Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.
From the order of the Homoptera, for example, Acyrthosipon spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis spp., Doralis spp., Drosicha spp., Dysaphis spp., Dysmicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes vaporariorum, Trioza spp., Typhlocyba spp., Unaspis spp., Viteus vitifolii.
From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
From the order of the Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber.
From the order of the Isoptera, for example, Reticulitermes spp., Odontotermes spp.
From the order of the Lepidoptera, for example, Acronicta major, Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana, Capua reticulana, Carpocapsa pomonella, Cheimatobia brumata, Chilo spp., Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp., Earias insulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp., Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella, Laphygma spp., Lithocolletis blancardella, Lithophane antennata, Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestra brassicae, Mocis repanda, Mythimna separata, Oria spp., Oulema oryzae, Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella, Pieris spp., Plutella xylostella, Prodenia spp., Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp.
From the order of the Orthoptera, for example, Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.
From the order of the Siphonaptera, for example, Ceratophyllus spp., Xenopsylla cheopis.
From the order of the Symphyla, for example, Scutigerella immaculata.
From the order of the Thysanoptera, for example, Baliothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.
From the order of the Thysanura, for example, Lepisma saccharina.
The phytoparasitic nematodes include, for example, Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp.
The compounds of the formula (I) according to the invention are distinguished in particular by strong activity against insects, parasites from the subclass of the Acari (Acarina) (such as mites, spider mites and/or ticks) and/or nematodes.
If appropriate, the compounds 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.
The active compounds 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.
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.
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.
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).
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.
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 polyoxyethylene 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, alkylaryl 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 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.
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.
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.
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.
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 according to the invention can be used in its commercially available formulations and in the use forms, prepared from these formulations, as a mixture with other active compounds, such as insecticides, attractants, sterilizing agents, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides, safeners, fertilizers or semiochemicals.
Particularly. favourable mixing partners are, for example, the following components:
Fungicides:
Inhibitors of nucleic acid synthesis
benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazol, mefenoxam, metalaxyl, metalaxyl-M, ofurace, oxadixyl, oxolinic acid
Inhibitors of mitosis and cell division
benomyl, carbendazim, diethofencarb, ethaboxam, fuberidazole, pencycuron, thiabendazole, thiophanate-methyl, zoxamide
Inhibitors of respiratory chain complex I
diflumetorim
Inhibitors of respiratory chain complex II
boscalid, carboxin, fenfuram, flutolanil, furametpyr, furmecyclox, mepronil, oxycarboxin, penthiopyrad, thifluzamide
Inhibitors of respiratory chain complex III
azoxystrobin, cyazofamid, dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, pyraclostrobin, picoxystrobin, trifloxystrobin
Decouplers
dinocap, fluazinam
Inhibitors of ATP production
fentin acetate, fentin chloride, fentin hydroxide, silthiofam
Inhibitors of amino acid biosynthesis and protein biosynthesis
andoprim, blasticidiN—S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil
Inhibitors of signal transduction
fenpiclonil, fludioxonil, quinoxyfen
Inhibitors of lipid and membrane synthesis
chlozolinate, iprodione, procymidone, vinclozolin
ampropylfos, potassium-ampropylfos, edifenphos, etridiazole, iprobenfos (IBP), isoprothiolane, pyrazophos
tolclofos-methyl, biphenyl
iodocarb, propamocarb, propamocarb hydrochloride, propamocarb-fosetylate
Inhibitors of ergosterol biosynthesis
fenhexamid,
azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenarimol, fenbuconazole, fluquinconazole, flurprimidole, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imazalil, imazalil sulphate, imibenconazole, ipconazole, metconazole, myclobutanil, nuarimol, oxpoconazole, paclobutrazole, penconazole, pefurazoate, prochloraz, propiconazole, prothioconazole, pyrifenox, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triforine, triticonazole, uniconazole, voriconazole, viniconazole,
aldimorph, dodemorph, dodemorph acetate, fenpropidin, fenpropimorph, spiroxamine, tridemorph,
naftifine, pyributicarb, terbinafine
Inhibitors of cell wall synthesis
benthiavalicarb, bialaphos, dimethomorph, flumorph, iprovalicarb, mandipropamid, polyoxins, polyoxorim, validamycin A
Inhibitors of melanin biosynthesis
capropamid, diclocymet, fenoxanil, phthalide, pyroquilon, tricyclazole
Resistance Inductors
acibenzolar-S-methyl, probenazole, tiadinil
Multisite
captafol, captan, chlorothalonil, copper salts such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulphate, copper oxide, oxine-copper and Bordeaux mixture, dichlofluanid, dithianon, dodine, dodine free base, ferbam, folpet, fluorofolpet, guazatine, guazatine acetate, iminoctadine, iminoctadine albesilate, iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, metiram zinc, propineb, sulphur and sulphur preparations containing calcium polysulphide, thiram, tolylfluanid, zineb, ziram
Further Fungicides
amibromdol, benthiazole, bethoxazin, capsimycin, carvone, chinomethionat, chloropicrin, cufraneb, cyflufenamid, cymoxanil, dazomet, debacarb, diclomezine, dichlorophen, dicloran, difenzoquat, difenzoquat metilsulphate, diphenylamine, ferimzone, flumetover, flusulfamide, fluopicolide, fluoroimide, fosetyl-aluminium, fosetyl-calcium, fosetyl-sodium, hexachlorobenzene, 8-hydroxy-quinoline sulphate, irumamycin, methasulfocarb, metrafenone, methyl isothiocyanate, mildiomycin, natamycin, nickel dimethyl dithiocarbamate, nitrothal-isopropyl, octhilinone, oxamocarb, oxyfenthiin, pentachlorophenol and salts, 2-phenylphenol and salts, piperalin, propanosine-sodium, proquinazid, pyribencarb, pyrrolnitrin, quintozene, tecloftalam, tecnazene, triazoxide, trichlamide, valiphenal, zarilamid,
Bactericides:
bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.
Insecticides/Acaricides/Nematicides:
Acetylcholine esterase (AChE) inhibitors
Carbamates,
for example alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, cloethocarb, dimetilan, ethiofencarb, fenobucarb, fenothiocarb, formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, triazamate
Organophosphates,
for example acephate, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos (-methyl/-ethyl), coumaphos, cyanofenphos, cyanophos, chlorfenvinphos, demeton-S-methyl, demeton-S-methylsulphone, dialifos, diazinon, dichlofenthion, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, dioxabenzofos, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosmethilan, fosthiazate, heptenophos, iodofenphos, iprobenfos, isazofos, isofenphos, isopropyl O-salicylate, isoxathion, malathion, mecarbam, methacrifos, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion (-methyl/-ethyl), phenthoate, phorate, phosalone, phosmet, phosphamidon, phosphocarb, phoxim, pirimiphos (-methyl/-ethyl), profenofos, propaphos, propetamphos, prothiofos, prothoate, pyraclofos, pyridaphenthion, pyridathion, quinalphos, sebufos, sulfotep, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon, vamidothion
Sodium channel modulators/voltage-dependent sodium channel blockers
Pyrethroids,
for example acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, deltamethrin, empenthrin (1R-isomer), esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenpyrithrin, fenvalerate, flubrocythrinate, flucythrinate, flufenprox, flumethrin, fluvalinate, fubfenprox, gamma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin, metofluthrin, permethrin (cis-, trans-), phenothrin (1R-trans-isomer), prallethrin, profluthrin, protrifenbute, pyresmethrin, resmethrin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin, terallethrin, tetramethrin (IR isomer), tralomethrin, transfluthrin, ZXI 8901, pyrethrins (pyrethrum)
DDT
oxadiazines,
for example indoxacarb
semicarbazones,
for example metaflumizone (BAS3201)
Acetylcholine receptor agonists/antagonists
chloronicotinyls,
for example acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam
nicotine, bensultap, cartap
Acetylcholine receptor modulators
spinosyns,
for example spinosad
GABA-controlled chloride channel antagonists
organochlorines,
for example camphechlor, chlordane, endosulphan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor
fiproles,
for example acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, vaniliprole
Chloride channel activators
mectins,
for example abamectin, emamectin, emamectin-benzoate, ivermectin, lepimectin, milbemycin
Juvenile hormone mimetics,
for example diofenolan, epofenonane, fenoxycarb, hydroprene, kinoprene, methoprene, pyriproxifen, triprene
Ecdysone agonists/disruptors
diacylhydrazines,
for example chromafenozide, halofenozide, methoxyfenozide, tebufenozide
Chitin biosynthesis inhibitors
benzoylureas,
for example bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron
buprofezin
cyromazine
Oxidative phosphorylation inhibitors, ATP disruptors
diafenthiuron
organotin compounds,
for example azocyclotin, cyhexatin, fenbutatin-oxide
Oxidative phosphorylation decouplers acting by interrupting the H-proton gradient
pyrroles,
for example chlorfenapyr
dinitrophenols,
for example binapacyrl, dinobuton, dinocap, DNOC, meptyldinocap
Site-I electron transport inhibitors
METIs,
for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad
hydramethylnon
dicofol
Site-II electron transport inhibitors
cyenopyrafen, cyflumetofen, rotenone
Site-III electron transport inhibitors
Acequinocyl, fluacrypyrim
Microbial disruptors of the insect gut membrane
Bacillus thuringiensis strains
Lipid synthesis inhibitors
tetronic acids,
for example spirodiclofen, spiromesifen,
tetramic acids,
for example spirotetramat, cis-3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1-azaspiro[4.5]dec-3-en-2-one
Carboxamides,
for example flonicamid
Octopaminergic agonists,
for example amitraz
Inhibitors of magnesium-stimulated ATPase,
propargite
nereistoxin analogues,
for example thiocyclam hydrogen oxalate, thiosultap-sodium
Ryanodine receptor agonists,
benzenedicarboxamides,
for example flubendiamide
anthranilamides,
for example Rynaxypyr (3-bromo-N-{4-chloro-2-methyl-6-[(methylamino)carbonyl]phenyl}-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide)
Biologicals, hormones or pheromones
azadirachtin, Bacillus spec., Beauveria spec., Codlemone, Metarrhizium spec., Paecilomyces spec., Thuringiensin, Verticillium spec.
Active compounds with unknown or unspecific mechanisms of action
A mixture with other known active compounds, such as herbicides, fertilizers, growth regulators, safeners, semiochemicals, or else with agents for improving the plant properties, is also possible.
When used as insecticides, the active compounds 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.
When used as insecticides, the active compounds 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 inhibitors which reduce degradation of the active compound after use in the environment of the plant, on the surface of parts of plants or in plant tissues.
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.
The compounds are employed in a customary manner appropriate for the use forms.
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 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, seeds, 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 compounds 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, watering, 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.
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.
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.
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.
The preferred transgenic plants or plant cultivars (obtained by genetic engineering) which are to be treated according to the invention include all plants which, by virtue of the genetic modification, received genetic material which imparts particular advantageous, useful traits to these plants. Examples of such traits are 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. Further and particularly emphasized examples of such traits are a better defence of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or viruses, and also increased tolerance of the plants to certain herbicidally active compounds. Examples of transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes, sugar beet, tomatoes, peas and other vegetable varieties, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton, tobacco, rice, canola and oilseed rape. Traits that are emphasized are in particular increased defence of the plants against insects, arachnids, nematodes and slugs and snails by virtue of toxins formed in the plants, in particular those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (referred to hereinbelow as “Bt plants”). Traits that are also particularly emphasized are the increased defence of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits that are furthermore particularly emphasized are the increased tolerance of plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate or phosphinotricin (for example the “PAT” gene). The genes which impart the desired traits in question can also be present in combination with one another in the transgenic plants. Examples of “Bt plants” which may be mentioned are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), KnockOut® (for example maize), StarLinkφ (for example maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned are maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soya bean), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, for example maize). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant cultivars having these genetic traits or genetic traits still to be developed, which plant cultivars will be developed and/or marketed in the future.
The plants listed can be treated according to the invention in a particularly advantageous manner with the compounds of the general formula I and/or the active compound mixtures according to the invention. The preferred ranges stated above for the active compounds or mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds or mixtures specifically mentioned in the present text.
The active compounds 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:
From the order of the Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
From the order of the Mallophagida and the suborders Amblycerina and Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.
From the order of the Diptera and the suborders Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.
From the order of the Siphonapterida, for example, Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
From the order of the heteropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
From the order of the Blattarida, for example, Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp.
From the subclass of the Acari (Acarina) and the orders of the Meta- and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp.
From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata), for example, Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
The active compounds of the formula (I) 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 reductions 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 compounds according to the invention.
The active compounds 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 compound, such as collars, ear marks, tail marks, limb bands, halters, marking devices and the like.
When used for cattle, poultry, pets and the like, the active compounds of the formula (I) 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 10000-fold dilution, or they can be used as a chemical bath.
It has furthermore been found that the compounds according to the invention also have a strong insecticidal action against insects which destroy industrial materials.
The following insects may be mentioned as examples and as preferred—but without any limitation:
Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus;
Hymenopterons, such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;
Termites, such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus;
Bristletails, such as Lepisma saccharina.
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.
With respect to possible additional additives, reference may be made to the insecticides and fungicides mentioned above.
The compounds according to the invention can likewise be employed for protecting objects which come into contact with saltwater or brackish water, in particular hulls, screens, nets, buildings, moorings and signalling systems, against fouling.
Furthermore, the compounds according to the invention, alone or in combinations with other active compounds, may be employed as antifouling agents.
In domestic, hygiene and stored-product protection, the active compounds 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:
From the order of the Scorpionidea, for example, Buthus occitanus.
From the order of the Acarina, for example, Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Omithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
From the order of the Araneae, for example, Aviculariidae, Araneidae.
From the order of the Opiliones, for example, Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
From the order of the Isopoda, for example, Oniscus asellus, Porcellio scaber.
From the order of the Diplopoda, for example, Blaniulus guttulatus, Polydesmus spp.
From the order of the Chilopoda, for example, Geophilus spp.
From the order of the Zygentoma, for example, Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
From the order of the Blattaria, for example, Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.
From the order of the Saltatoria, for example, Acheta domesticus.
From the order of the Dermaptera, for example, Forficula auricularia.
From the order of the Isoptera, for example, Kalotermes spp., Reticulitermes spp.
From the order of the Psocoptera, for example, Lepinatus spp., Liposcelis spp. From the order of the Coleoptera, for example, Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.
From the order of the Diptera, for example, Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa.
From the order of the Lepidoptera, for example, Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
From the order of the Siphonaptera, for example, Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
From the order of the Hymenoptera, for example, Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
From the order of the Anoplura, for example, Pediculus humanus capitis, Pediculus humanus corporis, Pemphigus spp., Phylloera vastatrix, Phthirus pubis.
From the order of the heteroptera, for example, Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
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.
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.
The compounds of the formula I-3 listed in the table below are known from WO 05/056556, WO 05/082907 and the international patent application having the application number PCT/EP 2006/001064, or they can be prepared by the processes described therein.
Phaedon test (spray treatment)
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvents and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
Discs of chinese cabbage leaves (Brassica pekinensis) are sprayed with an active compound preparation of the desired concentration and, after drying, populated with larvae of the mustard beetle (Phaedon cochleariae).
After the desired period of time, the effect in % is determined. 100% means that all beetle larvae have been killed, 0% means that none of the beetle larvae have been killed.
In this test, for example, the following compounds of the preparation examples show, at an application rate of 500 g/ha, an efficacy of ≧80%: I-3-1, I-3-3, I-3-4, I-3-5, I-3-6, I-3-7, I-3-9, I-3-10, I-3-11, I-3-12, I-3-13, I-3-14, I-3-15, I-3-16, I-3-17, I-3-19, I-3-21, I-3-22, I-3-25, I-3-26, I-3-27, I-3-28, I-3-29, I-3-30, I-3-31, I-3-32, I-3-35, I-3-37, I-3-38, I-3-39, I-3-42, I-3-47, I-3-48, I-3-49, I-3-50, I-3-52, I-3-53, I-3-54, I-3-55, I-3-56, I-3-57, I-3-58, I-3-59, I-3-60, I-3-61, I-3-62, I-3-63, I-3-64, I-3-65, I-3-66, I-3-67, I-3-68, I-3-70, I-3-71, I-3-72, I-3-73, I-3-74, I-3-75, I-3-76, I-3-77, I-3-78, I-3-79, I-3-80, I-3-81, I-3-82, I-3-83, I-3-85, I-3-86, I-3-87, I-3-88, I-3-89, I-3-90, I-3-91, I-3-92, I-3-93, I-3-94, I-3-95, I-3-96, I-3-98, I-3-99, I-3-101, I-3-102, I-3-104, I-3-109, I-3-110, I-3-111, I-3-112, I-3-113, I-3-114, I-3-115, I-3-116, I-3-117, I-3-118, I-3-119, I-3-120, I-3-121, I-3-122, I-3-123, I-3-124, I-3-125, I-3-127, I-3-128, I-3-129, I-3-131, I-3-132, I-3-133, I-3-135, I-3-136, I-3-137, I-3-138, I-3-139, I-3-140, I-3-141, I-3-142, I-3-144, I-3-145, I-3-146, I3-147, I-3-148, I-3-149, I-3-150, I-3-152, I-3-154, I-3-155, I-3-156, I-3-157, I-3-158, I-3-159, I-3-160, I-3-161, I-3-163, I-3-164, I-3-165, I-3-166, I-3-167, I-3-168, I-3-169, I-3-170, I-3-172, I-3-173, I-3-174, I-3-175, I-3-176, I-3-177, I-3-179, I-3-180, I-3-181, I-3-182, I-3-183, I-3-184, I-3-185, I-3-186, I-3-187, I-3-188, I-3-189, I-3-190, I-3-191, I-3-192, I-3-193, I-3-194, I-3-195, I-3-196, I-3-197, I-3-198, I-3-199, I-3-200, I-3-201, I-3-202, I-3-203, I-3-204, I-3-205, I-3-206, I-3-207, I-3-208, I-3-209, I-3-210, I-3-211, I-3-212, I-3-213, I-3-214, I-3-215, I-3-216, I-3-217, I-3-218, I-3-219, I-3-220, I-3-221, I-3-222, I-3-223, I-3-224, I-3-225, I-3-226, I-3-227, I-3-228, I-3-229, I-3-230, I-3-231, I-3-232, I-3-233, I-3-234, I-3-235, I-3-236, I-3-237, I-3-238, I-3-239, I-3-240, I-3-241, I-3-242, I-3-243, I-3-244, I-3-245, I-3-246, I-3-247, I-3-248, I-3-249, I-3-251, I-3-252, I-3-253, I-3-254, I-3-255, I-3-256, I-3-257, I-3-258, I-3-259, I-3-260, I-263, I-3-264, I-3-265, I-3-266, I-3-267, I-3-268, I-3-269, I-3-270, I-3-272, I-3-273, I-3-274, I-3-275, I-3-276, I-3-277, I-3-278, I-3-279, I-3-280, I-3-281, I-3-282, I-3-283, I-3-284, I-3-285, I-3-286, I-3-287, I-3-288, I-3-289, I-3-290, I-3-291, I-3-292, I-3-293, I-3-294, I-3-294, I-3-295, I-3-296, I-3-297, I-3-298, I-3-299, I-3-300, I-3-301, I-3-302, I-3-303, I-3-304, I-3-305, I-3-307, I-3-308, I-3-309, I-3-310, I-3-313, I-3-314, I-3-315, I-3-316, I-3-317, I-3-318, I-3-319, I-3-320, I-3-321, I-3-322, I-3-323, I-3-324, I-3-325, I-3-326, I-3-327, I-3-328, I-3-329, I-3-330, I-3-331, I-3-332, I-3-333, I-3-335, I-3-336, I-3-337, I-3-338, I-3-339, I-3-340, I-3-342, I-3-343, I-3-344, I-3-345, I-3-346, I-3-348, I-3-349, I-3-359, I-3-360, I-3-361, I-3-362, I-3-363, I-3-364, I-3-365, I-3-366, I-3-367, I-3-368, I-3-369, I-3-370, I-3-371, I-3-372, I-3-373, I-3-374, I-3-375, I-3-376, I-3-377, I-3-378, I-3-379, I-3-380, I-3-381, I-3-382, I-3-383, I-3-384, I-3-385, I-3-386, I-3-387, I-3-388, I-3-389, I-3-390, I-3-391, I-3-392, I-3-393, I-3-394, I-3-395, I-3-396, I-3-397, I-3-398, I-3-399, I-3-401, I-402, I-3-403, I-3-404, I-3-406, I-3-407, I-3-408, I-3-409-I-3-410.
Myzus test (spray treatment)
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
Discs of chinese cabbage leaves (Brassica pekinensis) which are infested by all stages of the green peach aphid (Myzus persicae) are sprayed with an active compound preparation of the desired concentration.
After the desired period of time, the effect in % is determined. 100% means that all aphids have been killed; 0% means that none of the aphids have been killed.
In this test, for example, the following compounds of the preparation examples show, at an application rate of 500 g/ha, an efficacy of ≧80%: I-3-5, I-3-6, I-3-7, I-3-8, I-3-9, I-3-11, I-3-13, I-3-16, I-3-31, I-3-32, I-3-35, I-3-43, I-3-72, I-3-84, I-3-87, I-3-124, I-3-184, I-3-201, I-3-260, I-3-268, I-3-323, I-3-349, I-3-378, I-3-379, I-3-384, I-3-385, I-3-386, I-3-389, I-3-390, I-3-395, I-3-408, I-3-409, I-3-410.
Spodoptera frugiperda test (spray treatment)
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
Discs of maize leaves (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, populated with caterpillars of the armyworm (Spodoptera frugiperda).
After the desired period of time, the effect in % is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed.
In this test, for example, the following compounds of the preparation examples show, at an application rate of 500 g/ha, an efficacy of >80%: I-3-1, I-3-5, I-3-6, I-3-8, I-3-9,1-3-10, I-3-11, I-3-12, I-3-13, I-3-14, I-3-15, I-3-16, I-3-17, I-3-21, I-3-23, I-3-24, I-3-25, I-3-27, I-3-28, I-3-30, I-3-31, I-3-32, I-3-33, I-3-35, I-3-36, I-3-37, I-3-38, I-3-45, I-3-46, I-3-47, I-3-48, I-3-49, I-3-50, I-3-51, I-3-58, I-3-59, I-3-60, I-3-61, I-3-62, I-3-64, I-3-66, I-3-67, I-3-68, I-3-71, I-3-72, I-3-76, I-3-79, I-3-81, I-3-84, I-3-86, I-3-87, I-3-88, I-3-89, I-3-91, I-3-92, I-3-94, I-3-96, I-3-101, I-3-102, I-3-109, I-3-112, I-3-113, I-3-114, I-3-115, I-3-116, I-3-117, I-3-118, I-3-119, I-3-121, I-3-122, I-3-123, I-3-124, I-3-125, I-3-127, I-3-128, I-3-129, I-3-140, I-3-141, I-3-142, I-3-143, I-3-144, I-3-145, I-3-146, I-3-147, I-3-149, I-3-150, I-3-152, I-3-154, I-3-155, I-3-156, I-3-157, I-3-158, I-3-159, I-3-160, I-3-161, I-3-164, I-3-165, I-3-174, I-3-176, I-3-181, I-3-182, I-3-183, I-3-186, I-3-187, I-3-188, I-3-191, I-3-192, I-3-193, I-3-198, I-3-202, I-3-203, I-3-205, I-3-206, I-3-207, I-3-214, I-3-215, I-3-216, I-3-217, I-3-218, I-3-220, I-3-221, I-3-224, I-3-225, I-3-236, I-3-242, I-3-245, I-3-246, I-3-247, I-3-248, I-3-249, I-3-250, I-3-251, I-3-254, I-3-255, I-3-256, I-3-257, I-3-259, I-3-260, I-3-262, I-3-263, I-3-280, I-3-281, I-3-287, I-3-298, I-3-299, I-3-300, I-3-302, I-3-304, I-3-306, I-3-308, I-3-309, I-3-312, I-3-317, I-3-318, I-3-319, I-3-320, I-3-322, I-3-325, I-3-327, I-3-328, I-3-329, I-3-330, I-3-331, I-3-334, I-3-336, I-3-337, I-3-341, I-3-342, I-3-346, I-3-347, I-3-348, I-3-349, I-3-361, I-3-365, I-3-370, I-3-371, I-3-372, I-3-378, I-3-381, I-3-382, I-3-397, I-3-400, I-3-401, I-3-402, I-3-404, I-3-408, I-3-409.
Tetranychus test, OP-resistant (spray treatment)
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
Discs of bean leaves (Phaseolus vulgaris) infested by all stages of the greenhouse red spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.
After the desired period of time, the effect in % is determined. 100% means that all spider mites have been killed; 0% means that none of the spider mites have been killed.
In this test, for example, the following compounds of the preparation examples show, at an application rate of 100 g/ha, an efficacy of ≧80%: I-3-58, I-3-76, I-3-315, I-3-316, I-3-318, I-3-329, I-3-330, I-3-346, I-3-348.
In this test, for example, the following compounds of the preparation examples show, at an application rate of 500 g/ha, an efficacy of ≧80%: I-3-6, I-3-11, I-3-14, I-3-17, I-3-27, I-3-38, I-3-68, I-3-79, I-3-81, I-3-92, I-3-125, I-3-246, I-3-248, I-3-251, I-3-260, I-3-262, I-3-283, I-3-301, I-3-302, I-3-309, I-3-388, I-3-389, I-3-320, I-3-334, I-3-337, I-3-340, I-3-348, I-3-359, I-3-362, I-3-365, I-3-382, I-3-401, I-3-407, I-3-410.
Lucilia cuprina test
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of water, and the concentrate is diluted with water to the desired concentration.
Vessels containing horse meat which had been treated with the preparation of active compound of the desired concentration are populated with Lucilia cuprina larvae.
After the desired period of time, the kill in % is determined. 100% means that all larvae have been killed; 0% means that none of the larvae have been killed.
In this test, for example, the following compounds of the preparation examples show, at a test concentration of 100 ppm, an efficacy of ≧80%: I-3-1, I-3-6, I-3-7, I-3-8, I-3-9, I-3-10, I-3-11, I-3-12, I-3-13, I-3-14, I-3-15, I-3-16, I-3-17, I-3-18, I-3-19, I-3-21, I-3-22, I-3-23, I-3-24, I-3-25, I-3-26, I-3-27, I-3-28, I-3-30, I-3-31, I-3-32, I-3-33, I-3-35, I-3-36, I-3-37, I-3-38, I-3-63, I-3-67, I-3-76, I-3-127, I-3-129, I-3-149, I-3-188, I-3-205, I-3-214, I-3-225, I-3-246, I-3-248, I-3-251, I-3-260, I-3-323, I-3-339, I-3-345, I-3-346, I-3-378, I-3-379, I-3-381, I-3-382, I-3-384, I-3-385, I-3-386, I-3-387, I-3-389, I-3-390, I-3-392, I-3-408, I-3-409.
Boophilus microplus test
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with solvent to the desired concentration.
The solution of active compound is injected into the abdomen (Boophilus microplus), the animals are transferred into dishes and stored in a climatized room.
After the desired period of time, the effect in % is determined. 100% means that none of the ticks has laid any fertile eggs.
In this test, for example, the following compounds show, at an application rate of 20 μg/animal, an effect of ≧80%: I-3-1, I-3-4, I-3-11, I-3-12, I-3-17, I-3-18, I-3-27, I-3-28, I-3-31, I-3-33, I-3-35, I-3-36, I-3-37, I-3-38, I-3-46, I-3-58, I-3-67, I-3-74, I-3-76, I-3-88, I-3-92, I-3-114, I-3-119, I-3-122, I-3-123, I-3-127, I-3-128, I-3-129, I-3-147, I-3-149, I-3-159, I-3-172, I-3-176, I-3-185, I-3-187, I-3-188, I-3-202, I-3-205, I-3-214, I-3-225, I-3-227, I-3-228, I-3-229, I-3-231, I-3-246, I-3-248, I-3-251, I-3-259, I-3-260, I-3-302, I-3-312, I-3-326, I-3-328, I-3-337, I-3-339, I-3-346, I-3-378, I-3-381, I-3-382, I-3-389.
Musca domestica test
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of water, and the concentrate is diluted with water to the desired concentration.
Vessels containing a sponge treated with the active compound preparation of the desired concentration are populated with (Musca domestica) adults.
After the desired period of time, the kill in % is determined. 100% means that all flies have been killed; 0% means that none of the flies have been killed.
In this test, for example, the following compound of the preparation examples shows, at a test concentration of 100 ppm, an efficacy of ≧80%: I-3-16.
Meloidogne test (MELGIN spray treatment)
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of water, and the concentrate is diluted with water to the desired concentration.
Vessels are filled with sand, solution of active compound, Meloidogyne incognita egg/larvae suspension and lettuce seeds. The lettuce seeds germinate and the plants develop. On the roots, galls are formed.
After the desired period of time, the nematicidal effect is determined in % by the gall formation. 100% means that no galls were found; 0% means that the number of galls on the treated plants corresponds to that of the untreated control.
In this test, for example, the following compounds of the preparation examples show, at a concentration of 20 ppm, an efficacy of ≧80%: I-3-7, I-3-41, I-3-42, I-3-46, I-3-59, I-3-61, I-3-64, I-3-65, I-3-66, I-3-70, I-3-71, I-3-78, I-3-80, I-3-82, I-3-96, I-3-101, I-3-115, I-3-116, I-3-117, I-3-118, I-3-120, I-3-127, I-3-131, I-3-133, I-3-135, I-3-136, I-3-137, I-3-138, I-3-163, I-3-164, I-3-166, I-3-198, I-3-200, I-3-262, I-3-298, I-3-311,1-3-321, I-3-331, I-3-334, I-3-369, I-3-407.
In this test, for example, the following compounds of the preparation examples show, at a concentration of 8 ppm, an efficacy of ≧80%: I-3-10, I-3-19, I-3-21, I-3-24.
In this test, for example, the following compounds of the preparation examples show, at a concentration of 4 ppm, an efficacy of ≧80%: I-3-1, I-3-29, I-3-30, I-3-99, I-3-193, I-3-194, I-3-227, I-3-230, I-3-275.
Nilaparvata lugens test (NILALU hydroponic treatment)
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
The preparation of active compound is pipetted into water. The stated concentration refers to the amount of active compound per volume unit of water (mg/l=ppm). The water is then infected with the brown planthopper (Nilaparvata lugens).
After the desired period of time, the effect in % is determined. 100% means that all planthoppers have been killed; 0% means that none of the planthoppers have been killed.
In this test, for example, the following compound of the preparation examples shows, at a concentration of 500 ppm, an efficacy of ≧80%: I-3-52.
Heliothis virescens test (HELIVI spray treatment)
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
Soya bean leaves (Glycine max.) are sprayed with an active compound preparation of the desired concentration and, after they have dried, populated with eggs of the tobacco budworm (Heliothis virescens).
After the desired period of time, the effect in % is determined. 100% means that all eggs have been killed; 0% means that none of the eggs have been killed.
In this test, for example, the following compound of the preparation examples shows, at a concentration of 500 ppm, an efficacy of ≧80%: I-3-50.
Activity increase by ammonium/phosphonium salts in combination with penetrants
Myzus persicae test
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration. If the addition of ammonium salts or ammonium salts and penetrants is required, these are in each case added in a concentration of 1000 ppm after dilution to the finished solution of the preparation.
Bell pepper plants (Capsicum annuum) which are heavily infested by the green peach aphid (Myzus persicaei) are treated by being sprayed with the active compound preparation at the desired concentration.
After the desired period of time, the kill in % is determined. 100% means that all animals have been killed; 0% means that none of the animals have been killed.
In this test, for example, the following compound of the preparation examples shows good efficacy: see table
Activity increase by ammonium/phosphonium salts in combination with penetrants
Aphis gossypii test
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration. If the addition of ammonium salts or ammonium salts and penetrants is required, these are in each case added in a concentration of 1000 ppm after dilution to the finished solution of the preparation.
Cotton plants (Gossypium hirsutum) which are heavily infested by the cotton aphid (Aphis gossypii) are treated by being sprayed to runoff point with the active compound preparation at the desired concentration.
After the desired period of time, the kill in % is determined. 100% means that all aphids have been killed; 0% means that none of the aphids have been killed.
In this test, for example, the following compound of the preparation examples shows good efficacy: see table
| Number | Date | Country | Kind |
|---|---|---|---|
| 10 2006 038 617.5 | Aug 2006 | DE | national |
| 10 2006 039 255.8 | Aug 2006 | DE | national |
| Filing Document | Filing Date | Country | Kind | 371c Date |
|---|---|---|---|---|
| PCT/EP07/05251 | 6/14/2007 | WO | 00 | 4/23/2009 |
