Title of Invention

"OPTICALLY ACTIVE PHTHALAMIDES OF THE FORMULA (I)''

Abstract Optically active phthalamides of the formula (I) A represents hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxy-C- C4-alkyl, CI-C6-alkylthio-C1-C4-alkyl, C1-C6-alkylsulfinyl-C1-C4-alkyl, (C1-C6-alkyl)-carbamoyl, q represents 0,1 or 2, R1    represents hydrogen or C1-C6-alkyl, R2    represents hydrogen or C1-C6-alkyl, Z represents CY4 E1    represents hydrogen or bromine, E2    represents hydrogen or fluorine, X1, X2, X3, X4 independently represent hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, nitro, cyano, C1-C6-alkylsulfonyloxy, C1-C6-haloalkylsulfonyIoxy, phenylsulfonyl-oxy, C1-C6-alkylthio-C1-C6-a!kyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfo-nyl-C1-C6-alkyl, C1-C6-alkylsulfonylamino, bis(C1-C6-alkylsulfonyl)amino or C1-C6-alkylcarbonyloxy, Y1, Y2, Y3, Y4 independently represent hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio or cyano.
Full Text Optically active phthalamides
The present invention relates to novel optically active phthalamides, to a plurality of processes for
their preparation and to their use as active compounds, hi particular their use as pesticides.
It is already known that numerous phthalamides have insecticidal properties (cf. EP-A 0919542,
EP-A 1 006 107). The activity of these compounds is good; however, it is sometimes unsatisfactory.
This invention now provides novel optically active phthalamides of the formula (I)
in which
A represents hydrogen, Ci-Ce-alkyl, C3-C6-alkenyl, Cs-Cg-alkynyl, C]-C6-alkoxy-CrC4-alkyl,
CpCe-aDcylthio-Ci-Cralkyl, CrCtf-alkylsulfinyl-CrQ-alkyl, (Ci-Ce-alkyl^arbamoyl,
q represents 0,1 or 2,
R1 represents hydrogen or C]-C6-alkyl,
R2 represents hydrogen or d -C6-alkyl,
Z represents CY4 or N,
E1 represents hydrogen or bromine,
E2 represents hydrogen or fluorine,
X1, X2, X3, X4 independently represent hydrogen, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, nitro, cyano,
Ci-Cs-alkylsulfonyloxy, Ci-Cg-haloallcylsulfonyloxy, phenylsulfonyloxy, Cj-Cfi-alkylthio-C)-
C6-alkyl, CrC6-alkylsulfrnyl-Ci-C6-alkyl, Ci-Cs-alkylsulfonyl-Ci-Cs-alkyl,
nylamino, bis(C]-C6-alkylsulfonyl)amino or Ci-Cs-alkylcarbonyloxy,
Y1, Y2, Y3, Y4 independently represent hydrogen, halogen, CpQ-alkyl, Ci-Cfi-haloalkyl,
alkoxy, Ci-C6-haloalkoxy, CpCe-alkylthio, Ci-C6-haloalkylthio or cyano.
In cases where R1 represents Ci-Ce-alkyl, R2 represents hydrogen and in cases where R2 represents
Ci-C6-alkyl R1 represents hydrogen.
Depending on the type and number of substituents, the compounds of the formula (I) may, if
appropriate, be present as geometrical and/or optical isomers or regioisomers or isomer mixtures
thereof of varying composition. What is claimed by the invention are both the pure isomers and the
isomer mixtures.
Furthermore, it has been found that optically active phthalamides of the formula (I) can be prepared
according to the following Scheme 1:
Scheme 1. Process for the preparation of optically active phthalamides of the formula (I)
Finally, it has been found that the compounds of the formula (1) according to the invention have very
good insecticidal properties and can be used both in crop protection and in the protection of materials
for controlling unwanted pests, such as insects, arachnids and mites.
The formula (I) provides a general definition of the compounds according to the invention. Preferred
substituents and ranges of the radicals given in the formulae mentioned above and below are
illustrated below.
A preferably represents hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, the
isomeric pentyls, the isomeric hexyls, allyl, butenyl, pentenyl, hexenyl, propargyl, butynyl,
pentyhyl, hexynyl, Ci-Cralkoxy-CrCalkyl, Cj-C4-alkylthio-C]-C2-alkyl, CrC4-
alkylsulfinyl-Ci-C2-alkyl, (CrC4-aIkyI)carbamoyl.
A particularly preferably represents hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or
tert-butyl, ally], butenyl, propargyl, butynyl, C]-C4-alkoxy-CrC2-alkyl (such as e.g. methoxymethyl,
methoxyethyl, ethoxymethyl, ethoxyethyl, n- or isopropoxymethyl), Ci-C4-alkylthio-
Ci-C2-alkyl (such as e.g. methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl,
n- or isopropylthiomethyl), CrC4-alkylsulflnyl-Ci-C2-alkyl (such as e.g. methylsulfinylmethyl,
methylsulfinylethyl, ethylsulfmylmethyl, ethylsulfmylethyl, n- or
isopropylsulfinylmethyl).
A very particularly preferably represents methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tertbutyl,
allyl, butenyl, propargyl, butynyl.
A especially preferably represents methyl, ethyl, n- or isopropyl.
q preferably represents 0.
q furthermore preferably represents 1.
q furthermore preferably represents 2.
R1 preferably represents hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl.
R1 particularly preferably represents hydrogen, methyl, ethyl, isopropyl or tert-butyl.
R1 very particularly preferably represents hydrogen.
R2 preferably represents hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl.
R2 particularly preferably represents hydrogen, methyl, ethyl, isopropyl or tert-butyl.
Rz yery particularly preferably represents hydrogen.
Z preferably represents CY4.
Z furthermore preferably represents N.
E1 preferably represents hydrogen.
E1 furthermore preferably represents bromine.
E2 preferably represents hydrogen.
E2 furthermore preferably represents fluorine,
X1, X2, X3, X4 independently preferably represent hydrogen, fluorine, chlorine, bromine, iodine, Cj-
Q-alkyl, Cj-C4-haloalkyl, nitro, cyano, Ci-C4-alkylsulfonyloxy, Ci-C4-haloalkylsulfonyloxy,
phenylsulfonyloxy, C]-C4-alkylthio-Ci-C4-alkyl, C]-C4-alkylsulfinyl-Ci-C4-alkyl, d-C4-alkylsulfonyl-
Cj-C4-alkyl, C]-C4-alkylsulfonylamino, bis(Cj-C4-alkylsulfonyl)amino or Cj-C4-
alkylcarbonyloxy.
X1, X2, X3, X4 independently particularly preferably represent hydrogen, fluorine, chlorine, bromine,
iodine, Ci-C4-alkyl (such as e.g. methyl, ethyl, n- or isopropyl, n-, iso, sec- or tert-butyl), Ci-
C4-haloalkyl (such as e.g. trifluoromethyl, trifluoroethyl, trichloromethyl), nitro, cyano, Ci-
C4-alkylsulfonyloxy (such as e.g. methylsulfonyloxy, ethylsiilfonyloxy, n- or isopropylsulfonyloxy,
n-, iso-, sec- or tert-butylsulfonyloxy), Ci-C4-haloalkylsulfonyloxy,
X1 very particularly preferably represents fluorine, chlorine, bromine, iodine, Cj-C4-alkylsulfonyloxy
(such as e.g. methylsulfonyloxy, ethylsulfonyloxy, n- or isopropylsulfonyloxy).
X2, X3, X4 independently very particularly preferably represent hydrogen.
Y1, Y2, Y3, Y4 independently preferably represent hydrogen, fluorine, chlorine, bromine, iodine, C|-
C4-alkyl, CrC4-haloalkyl, Ci-C4-alkoxy, CrC4-haloalkoxy, Ci-C4-alkylthio, CrC4-haloalkylthio
or cyano.
Y1, Y2, Y3, Y4 independently particularly preferably represent hydrogen, fluorine, chlorine, bromine,
iodine, Ci-C4-alkyl (such as e.g. methyl, ethyl, n- or isopropyl, n-, iso, sec- or tert-butyl), d-
C4-haloalkyl (such as e.g. trifluoromethyl, trifluoroethyl, trichloromethyl), C]-C4-alkoxy
(such as e.g. methoxy, ethoxy, n- or isopropoxy, n-, iso, sec- or tert-butoxy), Ci-C4-haloalkoxy
(such as e.g. trifluoromethoxy, trifluoroethoxy, trichloromethoxy).
Y1 very particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl.
Y2, Y3, Y4 independently very particularly preferably represent hydrogen.
In cases where R1 is methyl, ethyl, n- .or isopropyl, n-, iso-, sec- or tert-butyl, R2 represents hydrogen.
In cases where R2 is methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, R1 represents hydrogen.
Preference is furthermore given to compounds of the formula (I) in which R1 and R2 each represent
hydrogen.
Preference is furthermore given to compounds of the formula (I) in which X2, X3 and X4 each
represent hydrogen.
Preference is furthermore given to compounds of the formula (I) in which Y2, Y3 and Y4 each
represent hydrogen.
Saturated hydrocarbon radicals, such as alkyl, 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.
Halogen-substituted radicals, for example haloalkyl, are mono- or polysubstituted, up to the
maximum number of substituents possible. In the case of polyhalogenation, the halogen atoms can be
identical or different. Here, halogen represents fluorine, chlorine, bromine or iodine, in particular
fluorine, chlorine or bromine.
Preference, particular preference and very particular preference is given to compounds carrying the
substituents mentioned under preferred, particularly preferred and very particularly preferred,
respectively.
Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, can in each case be straightchain
or branched as far as this is possible - including in combination with heteroatoms, such as, for
example, in alkoxy.
Optionally substituted radicals may be mono- or polysubstituted, where in the case of
polysubstitution the substituents may be identical or different.
However, the general or preferred radical definitions or illustrations given above can also be
combined with one another as desired, i.e. between the respective ranges and preferred ranges. They
apply to the end products and, correspondingly, to the precursors and intermediates.
The preparation of the optically active phthalamides of the formula (I) according to the invention is
depicted in Scheme 1. Reaction conditions for the single reaction steps are identical to the reactions
described in EP-A 0 919 542 and EP-A 1 006 107 (cf. also the preparation examples below).
Compounds of the formula (I) may be obtained furthermore by synthesis of the racemic analogues
which racemates are subsequently resolved by customary methods, such as, for example, by
chromatography of the corresponding racemates on a chiral stationary phase. In this manner, it is
possible to resolve both the racemic end products or racemic intermediates into the two enantiomers.
Compounds of the formula (II) (cf. Scheme 1)
The compounds of formula (HI) may be obtained according to processes described in EP-A 1 418 169
and EP-A 1418 163.
Compounds of formula (IV) are either commercially available or can be prepared according to
JP 2001335571.
Compounds of formula (V) can be obtained by the process described in US 6,639,109.
The active compounds 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 and nematodes, which are encountered in agriculture, in forests, in
gardens and leisure facilities, in the protection of stored products and of materials, and in the hygiene
sector, and have good plant tolerance and favourable toxicity to warm-blooded animals and are
tolerated well by the environment. They may be preferably employed as plant protection agents. They
are active against normally sensitive and resistance species and against all or some stages of
development. The abovementioned pests include:
From the order of the bopoda, for example, Oniscus asellus, Armadillidium vulgare and Porcellio
scaber.
From the order of the Diplopoda, for example, Blaniulus guttulatus.
From the order of the Chilopoda, for example, Geopnilus carpophagus and Scutigera spp.
From the order of the Symphyla, for example, Scutigerella immaculata.
From the order of the Thysanura, for example, Lepisma saccharina.
From the order of the Collembola, for example, Onychiurus armatus.
From the order of the Orthoptera, for example, Acheta domesticus, Gryllotalpa spp., Locusta
migratoria migratorioides, Melanoplus spp. and Schistocerca gregaria.
From the order of the Blattaria, for example, Blatta orientalis, Periplaneta americana, Leuoophaea
maderae, Blattella gennanica.
From the order of the Deimaptera, for example, Forficula auricularia.
From the order of the Isoptera, for example, Reticulitermes spp.
From the order of the Phthiraptera, for example, Pediculus humanus corporis, Haematopinus spp.,
Linognathus spp., Trichodectes spp. and Damalinia spp.
From the order of the Thysanoptera, for example, Hercinothrips femoralis, Thrips tabaci, Thrips palmi
and Frankliniella occidental.
From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma
quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.
From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes
vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi,
Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum
avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus,
Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens,
Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.
From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius,
Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella,
Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis
citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Mamestra brassicae,
Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chile spp.,
Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella,
Hofinannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fiimiferana, Clysia
ambiguella, Homona magnanhna, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae.
From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica,
Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa
decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis,
Atomaria spp., Ory2aephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus,
Cosmopolites sordidus, Ceuthorrhynchus assimih's, Hypera postica, Dermestes spp., Trogoderma spp.,
Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus bololeucus,
Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha
melolontha, Amphimallon solstitialis, Costelytra zealandica and Lissorhoptrus oryzophilus.
From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp.,
Monomorium pharaonis and Vespa spp.
From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila
melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp.,
Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp.,
Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami,
Ceratitis capftata, Dacus oleae, Tipula paludosa, Hylemyia spp. and Liriomyza spp.
From the order of the Siphonaptera, for example, Xenopsylla oheopis and Ceratophyllus spp.
From the class of the Arachnida, for example, Scorpio maurus, Latrodectus mactans, Acarus siro,
Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora,
Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,
Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus
spp., Hemitarsonemus spp., Brevipalpus spp.
The phytoparasitic nematodes include, for example, Pratylenchus spp., Radopholus simflis,
Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp.,
Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.
The compounds of the formula (I) according to the invention have in particular excellent activity
against caterpillars and beetle larvae.
If appropriate, the compounds according to the invention can, at certain concentrations or application
rates, also be used as herbicides or microbicides, for example as fungicides, antimycotics and
bactericides. If appropriate, they can also be employed as intermediates or precursors for the synthesis
of other active compounds.
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, environment or storage
space by the customary treatment methods, for example by immersion, spraying, evaporation,
fogging, scattering, painting on and, in the case of propagation material, in particular in the case of
seeds, also by applying one or more coats.
The active compounds can be converted to the customary formulations, such as solutions, emulsions,
wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspensionemulsion
concentrates, natural and synthetic materials impregnated with active compound 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.
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 or 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 butane! 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 dimethylformamide and dimethyl sulphoxide, and also
water.
As solid carriers there are suitable:
for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz,
attapulgfte, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly
disperse silica, alumina and silicates; as solid carriers for granules there are suitable: 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 sawdust,
coconut shells, maize cobs and tobacco stalks; as emulsifiers and/or foam-formers there are suitable:
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 hydrorysates; as dispersants there are suitable: for example
lignosulphite waste liquors and methylcellulose.
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. Other additives can be mineral and vegetable oils.
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.
The fonnulations generally comprise between 0.1 and 95% 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 fonnulations, as a mixture with other active
compounds, such as insecticides, attractants, sterilizing agents, bactericides, acaricides, nematicides,
fungicides, growth-regulating substances or herbicides. The insecticides include, for example,
phosphoric acid esters, carbamates, carboxylates, chlorinated hydrocarbons, phenylureas and
substances produced by microorganisms, inter alia.
Particularly favourable mixing components are, for example, the following compounds:
Fungicides:
2-phenylphenol; 8-hydroxyquinoline sulfate; acibenzolar-S-methyl; aldimorph; amidoflumet; ampropylfos;
ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin; benalaxyl; benalaxyl-
M; benodanil; benomyl; benthiavalicarb-isopropyl; benzamacril; benzamacril-isobutyl; bilanafos; binapacryl;
biphenyl; bitertanol; blasticidin-S; boscalid; bromuconazole; bupirimate; buthiobate; butylamine;
calcium polysulfide; capsimycin; captafbl; captan; carbendazim; carboxin; carpropamid; carvone;
chinomethionat; chlobenthiazone; chlorfenazole; chloroneb; chlorothalonil; chlozolinate; clozylacon;
cyazofamid; cyflufenamid; cymoxanil; cyproconazole; cyprodinil; cyprofuram; Dagger G; debacarb;
dichlofluanid; dichlone; dichlorophen; diclocymet; diclomezine; dicloran; diethofencarb; difenoconazole;
diflumetorim; dimethirimol; dimethomorph; dimoxystrobin; diniconazole; diniconazole-M;
dinocap; diphenylamine; dipyrithione; ditalimfos; dithianon; dodiiie; drazoxolon; edifenphos; epoxiconazole;
ethaboxam; ethirimol; etridiazole; famoxadone; fenamidone; fenapanil; fenarimol; fenbuconazole;
fenfuram; fenhexamid; fenitropan; fenoxanil; fenpiclonil; fenpropidin; fenpropimorph; ferbani;
fluazinam; flubenzimine; fludioxonil; flumetover; flumorph; fluoromide; fluoxastrobin; fluquinconazole;
flurprimidol; flusilazole; flusulfamide; flutolanil; flutriafol; folpet; fosetyl-Al; fosetyl-sodium;
fuberidazole; furalaxyl; furametpyr; furcarbanil; furmecyclox; guazatine; hexachlorobenzene; hexaconazole;
hymexazol; imazalil; imibenconazole; iminoctadine triacetate; iminoctadine tris(albesilate);
iodocarb; ipconazole; iprobenfos; iprodione; iprovalicarb; irumamycin; isoprothiolane; isovaledione;
kasugamycin; kresoxim-methyl; mancozeb; maneb; meferimzone; mepanipyrim; mepronil; metalaxyl;
metalaxyl-M; metconazole; methasulfocarb; methfuroxam; metiram; metominostrobin; metsulfovax;
mildiomycin; myclobutanil; myclozolin; natamycin; nicobifen; nitrothal-isopropyl; noviflumuron; nuarimol;
ofiirace; orysastrobin; oxadixyl; oxolinic acid; oxpoconazole; oxycarboxin; oxyfenthiin; paclobutrazol;
pefurazoate; penconazole; pencycuron; phosdiphen; phthalide; picoxystrobin; piperalin; polyoxins;
polyoxorim; probenazole; prochloraz; procymidone; propamocarb; propanosine-sodium; propiconazole;
propineb; proquinazid; prothioconazole; pyracloslrobin; pyrazophos; pyrifenox; pyrimethanil;
pyroquilon; pyroxyfur, pyrrohitrine; quinconazole; quinoxyfen; quintozene; simeconazole; spiroxamine;
sult\ir; tebuconazole; tecloflalam; tecnazene; tetcyclacis; tetraconazole; thiabendazole; thicyofen;
thifluzamide; miophanate-methyl; thiram; tioxymid; tolclofos-methyl; tolylfluanid; triadimefon; triadimenol;
triazbvrtil; triazoxide; tricyclamide; tricyclazole; tridemorph; trifloxystrobin; triflumizole; triforine;
triticonazcle; uniconazole; validamycin A; vinclozolin; zineb; ziram; zoxamide; (2S)-N-[2-[4-
[[3-(4-chJorophenyl)-2-propynyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(memykulfbnyl)amino]-
butanamide; l-(l-naphthalenyl}-lH-pyrrol-2,5-dione; 2,3,5,6-tetrachloro-4-(methylsulfonyl)-pyridine;
2-amino-4-metby]-N-phenyl-5-miazolecarboxamide; 2-chloro-N-(2J-dihydro-l,l,3-trimethyl-lH-inden-
4-yl)-3-pyridinecarboxamide; S^^-trichloro-pyridinedicarbonitrile; actinovate; cis-l-(4-chlorophenyl)-
2-(lH-l,2,4-ttiazol-l-yl)-cycloheptanol; methyl l-(2,3-dihydro-2s2-dimethyI-lH-inden-1-yl)-
lH-imidazole-5-carboxylate; mono potassium carbonate; N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide;
N-bvrtyl-8-(ljl-dimethyIethyl)-l-oxaspiro[4.5]decan-3-amine; sodium tetrathiocarbonate;
and copper salts and preparations, such as Bordeaux mixture; copper hydroxide; copper naphthenate;
copper oxychloride; copper sulphate; cufraneb; copper oxide; mancopper; oxine-copper.
Bactericides:
bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone,
furancarboxylic acid, oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphate and
oflier copper preparations.
1.1 Carbamates (e.g. alanycarb, aldicarb, aldoxycarb, allyxycarb, arninocarb, azamethiphos, bendiocarb,
benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosuUan,
chloetiiocarb, coumaphos, cyanofenphos, cyanophos, dimetilan, ethiofencarb, fenobucarb, fenothiocarb,
formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl,
pirimicarb, promecarb, propoxur, miodicarb, thiofanox, triazamate, trimethacarb, XMC, xyrylcarb)
1.2 Organophosphates (e.g. acephate, azamefliiphos, azinphos (-methyl, -ethyl), bromophos-ethyl,
bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chlorethoxyfos, chlorfenvinphos,
chlormephos, chlorpyrifos (-methylAethyl), coumaphos, cyanofenphos, cyanophos, chlorfenvinphos,
demeton-s-methyl, demeton-s-methylsulphon, dialifos, diazinon, dichlofenthion, dichlorvos/ddvp, dicrotophos,
dimethoate, dimethylvinphos, dioxabenzofos, disulfoton, epn, ethion, ethoprophos, etrimfos,
famphur, fenamiphos, fenhrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosmethilan,
fosthiazate, heptenophos, iodofenphos, iprobenfos, isazofos, isofenphos, isopropyl o-salicylate,
isoxathion, malathion, mecarbam, methacrifos, methamidophos, memidathion, mevinphos, monocrotophos,
naled, omethoate, oxydemeton-methyl, parathion (-methyl/-ethyl), phenthoate, phorate,
phosalone, phosmet, phosphamidon, phosphocarb, phoxim, pirimiphos (-methylAethyl), profenofos,
propaphos, propetamphos, prothiofos, prothoate, pyraclofos, pyridaphenthion, pyridathion, quinalphos,
sebufos, sulfotep, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazopfaos,
triclorfon, vamidothion)
2, Sodium channel modulators /voltage dependant sodium channel blockers
2.1 Pyrethroids (e.g. acrinatiirin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin,
bioallethrin-s-cyclopentyl-isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, ciscypermefhrin,
cia-resmethrin, cis-pennethrin, clocythrin, cycloprothrin, oyfluthrin, cyhalothrin, cypermethrin
(alpha-, beta-, theta-, zeta-), oyphenothrin, DDT, deltamethrin, empenthrin (IR-isomer), esfenvalerate,
etofenprox, fenfluthrin, fenpropathrin, fenpyrithrin, fenvalerate, flubrocythrinate, fhicyflirinate,
flufenprox, flumethrin, fluvalinate, fubfenprox, gamma-cyhalothrin, imiprothrin, kadethrin, lambdacyhalotiirin,
rnetofluthrin, permethrin (cis-, trans-), phenothrin (IR-trans isomer), prallethrin, profluthrin,
protrifenbute, pyresmethrin, resmethrin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin, terallethrin,
tetramethrin (IR-isomer), tralomethrin, transfluthrin, ZXI8901, pyrethrins (pyrethrum))
2.2 Oxadiazine (e.g. indoxacarb)
3, Acetylcholme receptor agorrists/-antagomsts
3.1 Chloronicotinyls/neonicotinoids (e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram,
nithiazine, thiacloprid, thiamethoxam)
3.2 nicotine, bensultap, cartap
4, Acetylcholme receptor modulators
4.1 Spinosyns (e.g. spinosad)
5, GABA gated chloride channel antagonists
5.1 Cyclodiene organochJorines (e.g. campheohlor, chlordane, endosulfan, gamma-HCH, HCH,
heptachlor, lindane, methoxychlor
5.2 Fiproles (e.g. acetoprole, ethiprole, fipronil, vaniliprole)
6, Chloride channel activators
6.1 Mectins (e.g. abamectin, avermectin, emamectin, emamectin-benzoate, ivermectin, milbemectin,
milbemycin)
7, Juvenile hormone mimics
(e.g. diofenolan, epofenonane, fenoxycarb, hydroprene, kinoprene, methoprene, pyriproxifen, triprene)
-13-
8. Ecdysone agonists/disrupters
8,1 Diacylhydrazines (e.g. chromafenozide, halofenozide, methoxyfenozide, tebufenozide)
9. Inhibitors ofchitin biosynthesis
9.1 Benzoylureas (e.g. bistrifluron, chlofluazuron, diflubenzuron, fhiazuron, flucycloxuron, flufenoxuron,
hexaflumuron, lufenuron, novahjron, noviflumuron, penfluron, teflubenzuron, triflumuron)
9.2 buprofbziiJ
9.3 cyromazine
10. Inhibitors of oxidativephosphory lotion, ATP-disrvptors
10.1 diafenthiuron
10.2 Organotins (e.g. azocyclotin, cyhexatin, fenbutatin-oxide)
11. Decoupler ofoxidatrvephoshorylation by diruption of Hproton gradient
11.1 Pyrroles (e.g, chlorfenapyr)
11.2 Dinitrophenoles (e.g. binapacyr], dinobuton, dinocap, DNOC)
12. Site I electron transport inhibitors
12.1 METI's (e.g. fenazaqujn, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad)
12.2 hydramethylnone
12.3 dicofol
73. Site II electron transport inhibitors
13.1 rotenone
14. Site III electron transport inhibitors
14.1 acequinocyl, fluacrypyrim
15. Microbial disrupters of insect midgut membranes
Bacillus thuringiensis strains
16. Inhibitors of lipid synthesis
16.1 Tetronic acid insecticides (e.g. spirodiclofen, spiromesifen)
16.2 Tetramic acid insecticides [e.g. 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-l-azaspiro[4.5]dec-3-
en-4-yl ethyl carbonate (alias: carbonic acid, 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-l-azaspiro-
[4.5]dec-3-en-4-yl ethyl ester, CAS-Reg.-No.: 382608-10-8) and carbonic acid, cis-3-(2,5-dimethylphenyl)-
8-methoxy-2-oxo-l-azaspiro[4.5]dec-3-en-4-yl ethyl ester (CAS-Reg.-No.: 203313-25-1)]
17. Carboxamides
(e.g. flonicamid)
18. Octopaminergic agonists
(e.g. amitraz)
19. Inhibitors ofmagnesiwn stimulatedATPase
(e.g. propargite)
20. Phthalamides
(e.g. Ntl.
fluoroinethyl)ethyl]phenyl]-l-benzenedicarboxamide (CAS-Reg.-No.: 272451-65-7, flubendiamide))
21. Nereistoxin analogues
(e.g. thiocyclam hydrogen oxalate, thiosultap-sodium)
22. Biologica, hormones or pheromones
(e.g. azadirachtin, Bacillus spec., Beauveria spec., codlemone, Metarrhizium spec., PaecUomyces
spec., thuringiensin, Verticillium spec.)
23. Compounds of unknown or non-specific mode of action
23.1 Fumigants (e.g. aluminium phosphide, methyl bromide, sulfuryl fluoride)
23.2 Selective feeding Mockers (e.g. cryolite, flonicamid, pymetrozine)
23.3 Mite growth inhibitors (e.g. clofentezine, etoxazole, hexythiazox)
23.4 amidoflumet, benclothiaz, benzoximate, bifenazate, bromopropylate, buprofezin, chinomethionat,
chlordimeform, chlorobenzilate, chloropicrin, clothiazoben, cycloprene, cyfhimetofen, dicyclanil,
fenoxacrim, fentrifanil, flubenzimine, flufenerim, flutenzin, gossyplure, hydramethylnone,
japonilure, metoxadiazone, petroleum, piperonyl butoxide, potassium oleate, pyrafluprole, pyridalyl,
pyriprole, sulfluramid, tetradifon, tetrasul, triarathene, verbutin
further the compound 3-methyl-phenyl-propylcarbamate (Tsumacide Z), th& compound 3-(5-chloro-
3-pyridinyl)-8-(2,2}2-trifluoroethylo isomer (CAS-Reg.-Nr. 185984-60-5) (cf. WO 96/37494, WO
98/25923), and preparations comprising insecticidal active plant extracts, nematodes, fungi or viruses.
A mixture with other known active compounds, such as herbicides, fertilizers, growth regulators,
safeners and/or semiochemicals 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 vicinity 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
0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight.
The compounds are employed in a customary manner appropriate for the use forms.
When used against hygiene pests and pests of stored products, the active compound is distinguished
by an excellent residual action on wood and clay as well as a good stability to alkali on limed
substrates.
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, if
appropriate in combination with conventional methods (Genetically Modified Organisms), and parts
thereof are treated. The term "parts" or "parts of plants" or "plant parts" has been explained above.
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 certain 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 superaddiiive
("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 to 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, better 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 transgenic plants or plant cultivars (i.e. those obtained by genetic engineering) which are preferably
to be treated according to the invention include all plants which, in the genetic modification, received
genetic material which imparted particularly 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, better quality and/or a higher nutritional value of the
harvested products, better storage stability and/or processabiliry 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, 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 and
oilseed rape. Traits that are emphasized are in particular increased defence of the plants against insects,
arachnids, nematodes and worms by 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), CryllA, CrymA, CryIHB2, Cry9c, Cry2Ab, Cry3Bb and CryBF and also combinations
thereof) (hereinbelow referred to as "Bt plants"). Traits that are also particularly emphasized are the
increased defence of the plants against fungi, bacteria and viruses by systemic acquired resistance
(SAR), systemin, phytoalexius, elicitors and resistance genes and correspondingly expressed proteins
and toxins. Traits that are furthermore particularly emphasized are the increased tolerance of the 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), StarLink® (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), BVU® (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 plants 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 (ectoparasites), 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., Linogaathus spp., Pediculus spp.,
Phtirus spp. and Solenopotes spp.
From the order of the Mallophagida and the suborders Amblycerina and Ischnocerina, for example,
Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Wemeckiella spp., Lepikentron spp.,
Damalina spp., Trichodectes spp. and 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. and Melophagus spp.
From the order of the Siphonapterida, for example Pulex spp., Ctenocephalides spp., Xenopsylla spp.
and Ceratophyllus spp.
From the order of the Heteropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp. and
PanstrOngylus spp.
From the order of the Blattarida, for example Blatta orientalis, Periplaneta americana, Blattella
germanica and Supella spp.
From the subclass of the Acaria (Acarida) and the orders of the Meta- and Mesostigmata, for
example, Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophihis
spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp,, Rhipicephalus spp., Dermanyssus spp.,
Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroa spp.
From the order of the Actinedida (Prostigmata) und 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., Rnemidocoptes spp., Cytodites spp. and Laminosioptes spp.
They have, for example, excellent activity against the development stages of ticks, such as, for
example, Boophilus microplus, and against parasitic flies, such as, for example, Lucilia cuprina and
against fleas, such as, for example, Ctenocephalides felis.
The active compounds of the formula (T) 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 compounds
according to the invention.
The active compounds according to the invention are used hi the veterinary sector in a known manner
by entera] 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 10 000-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 a 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 minutes;
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 cards, leather, wood and processed wood
products and coating compositions.
Wood and processed wood products are materials to be protected, especially preferably, from insect
infestation.
Wood and processed wood products which can be protected by the agents according to the invention
or mixtures comprising these are to be understood as meaning, for example:
Building timber, wooden beams, railway sleepers, bridge components, boat jetties, wooden vehicles,
boxes, pallets, containers, telegraph poles, wood panelling, wooden windows and doors, plywood,
chipboard, joinery or wooden products which are used quite generally in house-building or in
buildingjoinery.
The active compounds can be used as such, in the form of concentrates or in generally customary
formulations, such as powders, granules, solutions, suspensions, emulsions or pastes.
The formulations mentioned can be prepared in a manner known per se, for example by mixing the
active compounds with at least one solvent or diluent, emulsifier, dispersing agent and/or binder or
fixing agent, a water repellent, if appropriate siccatives and UV stabilizers and if appropriate
dyestuffs and pigments, and also other processing auxiliaries.
The insecticidal compositions or concentrates used for the preservation of wood and wood-derived
timber products comprise the active compound according to the invention in a concentration of
0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
The amount of the compositions or concentrates employed depends on the nature and occurrence of
the insects and on the medium. The optimum amount employed can be determined for the use in each
case by a series of tests. In general, however, it is sufficient to employ 0.0001 to 20% by weight,
preferably 0.001 to 10% by weight, of the active compound, based on the material to be preserved.
Solvents and/or diluents which are used are an organic chemical solvent or solvent mixture and/or an
oily or oil-like organic chemical solvent or solvent mixture of low volatDity and/or a polar organic
chemical solvent or solvent mixture and/or water, and if appropriate an emulsifier and/or wetting
agent.
Organic chemical solvents which are preferably used are oily or oil-like solvents having an
evaporation number above 35 and a flashpoint above 30°C, preferably above 45°C. Substances which
are used as such oily or oil-like water-insoluble solvents of low volatility are appropriate mineral oils
or aromatic fractions thereof, or solvent mixtures containing mineral oils, preferably white spirit,
petroleum and/or alkylbenzene.
Mineral oils having a boiling range from 170 to 220°C, white spirit having a boiling range from 170
to 220°C, spindle oil having a boiling range from 250 to 3.50°C, petroleum and aromatics having a
boiling range from 160 to 280°C, turpentine oil and the like, are advantageously employed.
In a preferred embodiment, liquid aliphatic hydrocarbons having a boiling range from 180 to 210°C
or high-boiling mixtures of aromatic and aliphatic hydrocarbons having a boiling range from 180 to
220°C and/or spindle oil and/or monochloronaphthalene, preferably a-monochloronaphthalene, are
used.
The organic oily or oil-like solvents of low volatility which have an evaporation number above 35
and a flashpoint above 30°C, preferably above 45°C, can be replaced in part by organic chemical
solvents of high or medium volatility, provided that the solvent mixture likewise has an evaporation
number above 35 and a flashpoint above 30°C, preferably above 45°C, and that the
insecticide/fungicide mixture is soluble or emulsifiable in this solvent mixture.
According to a preferred embodiment, some of the organic chemical solvent or solvent mixture is
replaced by an aliphatic polar organic chemical solvent or solvent mixture. Aliphatic organic
chemical solvents containing hydroxyl and/or ester and/or ether groups, such as, for example, glycol
ethers, esters or the like, are preferably used.
Organic chemical binders which are used in the context of the present invention are the synthetic
resins and/or binding drying oils which are known per se, are water-dilutable and/or are soluble or
dispersible or emulsifiable in the organic chemical solvents employed, hi particular binders consisting
of or comprising an acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin,
polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin,
phenolic resin, hydrocarbon resin, such as indene-cumarone resin, silicone resin, drying vegetable oils
and/or drying oils and/or physically drying binders based on a natural and/or synthetic resin.
The synthetic resin used as the binder can be employed in the form of an emulsion, dispersion or
solution. Bitumen or bituminous substances can also be used as binders in an amount of up to 10% by
weight. DyestuSs, pigments, water-repelling agents, odour correctants and inhibitors or anticorrosive
agents and the like which are known per se can additionally be employed.
It is preferred according to the invention for the composition or concentrate to comprise, as the
organic chemical binder, at least one alkyd resin or modified alkyd resin and/or a drying vegetable
oil. Alkyd resins having an oil content of more than 45% by weight, preferably 50 to 68% by weight,
are preferably used according to the invention.
All or some of the binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer
(mixture). These additives are intended to prevent evaporation of the active compounds and
crystallization or precipitation. They preferabry replace 0.01 to 30% of the binder (based on 100% of
the binder employed).
The plasticizers originate from the chemical classes of phthalic acid esters, such as dibutyl, dioctyl or
benzyl butyl phthalate, phosphoric acid esters, such as tributyl phosphate, adipic acid esters, such as
di-(2-ethylhexyl) adipate, stearates, such as butyl stearate or amyl stearate, oleates, such as butyl
oleate, glycerol ethers or higher molecular weight glycol ethers, glycerol esters and ptoluenesulphonic
acid esters.
Fixing agents are based chemically on polyvinyl alky] ethers, such as, for example, polyvinyl methyl
ether or ketones, such as benzophenone or ethylenebenzophenone.
Possible solvents or diluents are, in particular, also water, if appropriate as a mixture with one or
more of the abovementioned organic chemical solvents or diluents, emulsifiers and dispersing agents.
Particularly effective preservation of wood is achieved by impregnation processes on a large
industrial scale, for example vacuum, double vacuum or pressure processes.
The ready-to-use compositions can also comprise other insecticides, if appropriate, and also one or
more fungicides, if appropriate.
Possible additional mixing partners are, preferably, the insecticides and fungicides mentioned in
WO 94/29 268. The compounds mentioned hi this document are an explicit constituent of the present
application.
Especially preferred mixing partners which may be mentioned are insecticides, such as chlorpyriphos,
phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid,
M-25, flufenoxuron, hexaflumuron, transfluthrin, thiacloprid, methoxyfenozide, triflumuron,
clothianidin, spinosad, tefluthrin, '
and also fungicides, such as epoxyconazole, hexaconazole, azaconazo'le, propiconazole,
tebuconazole, cyproconazole, metconazole, imazalil, dichlorfluanid, tolylfluanid, 3-iodo-2-propinylbutyl
carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one.
The compounds according to the invention can at the same time be employed for protecting objects
which come into contact with saltwater or brackish water, such as hulls, screens, nets, buildings,
moorings and signalling systems, against fouling.
Fouling by sessile Oligochaeta, such as Serpulidae, and by shells and species from the Ledamorpha
group (goose barnacles), such as various Lepas and Scalpellum species, or by species from the
Balanomorpha group (acorn barnacles), such as Balanus or Pollicipes species, increases the fractional
drag of ships and, as a consequence, leads to a marked increase in operational costs owing to higher
energy consumption and additionally frequent residence in the dry dock.
Apart from fouling by algae, for example Ectocarpus sp. and Ceramium sp., fouling by sessile
Entomostraka groups, which come under the generic term Cirripedia (cirriped crustaceans), is of
particular importance.
Surprisingly, it has now been found that the compounds according to the invention, alone or in
combination with other active compounds, have an outstanding antifouling action.
Using the compounds according to the invention, alone or in combination with other active
compounds, allows the use of heavy metals such as, for example, in bis(trialkyltin) sulphides, tri-Hbutyltin
laurate, tri-tt-butyltin chloride, copper(I) oxide, triethyltin chloride, tri-«-butyl(2-phenyl-4-
chlorophenoxy)tin, tributyltin oxide, molybdenum disulphide, antimony oxide, polymeric butyl
titanate, phenyl-(bispyridine)-bismtrfh chloride, tri-n-butyltin fluoride, manganese
ethylenebisthiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisthiocarbamate, zinc salts
and copper salts of 2-pyridinethiol 1-oxide, bisdimethyldithiocarbamoylzinc ethylenebisthiocarbamate,
zinc oxide, copper(I) ethylene-bisdithiocarbamate, copper thiocyanate, copper
naphthenate and tributyltin halides to be dispensed with, or the concentration of these compounds to
be substantially reduced.
If appropriate, the ready-to-use antifouling paints can additionally comprise other active compounds,
preferably algicides, fungicides, herbicides, molluscicides, or other antifouling active compounds.
Preferably suitable components in combinations with the antifouling compositions according to the
invention are:
algicides such as 2-ter/-butylamino-4-cyclopropylammo-6-merhylthio-l,335-triazine, dichlorophen,
diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen, quinociamine and terbutryn;
fungicides such as benzo[6]thiophenecarboxylic acid cyclohexylamide S,S-dioxide, dichlofluanid,
fluorfolpet, 3-iodo-2-propinyl butylcarbamate, tolylfluanid and azoles such as azaconazole, oyproconazole,
epoxyconazole, hexaconazole, metconazole, propiconazole and tebuconazole; molluscicides such
as fentin acetate, metaldehyde, methiocarb, niclosamid, thiodicarb and trimethacarb; or conventional
antifouling active compounds such as 4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatryl
sulphone, 2-(K,N-dhnethylthiocarbamoylthio)-5-nitrothia2yl, potassium, copper, sodium and zinc salts
of 2-pyridinethiol 1-oxide, pyridine-triphenylborane, tetrabutyldistannoxane, 2,3,5,6-tetrachloro-4-
(methylsulphonyl)-pyridine, 2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulphide and
2,4,6-trichlorophenyhnaleiimide.
The antifouling compositions used comprise the active compound according to the invention of the
compositions according to the invention in a concentration of 0.001 to 50% by weight, in particular
0.01 to 20% by weight
Moreover, the antifouling compositions according to the invention comprise the customary
components such as, for example, those described in Ungerer, Chem, Ind, 1985, 37, 730-732 and
Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.
Besides the algicidal, fungicidal, molluscicidal active compounds and insecticidal active compounds
according to the invention, antifouling paints comprise, in particular, binders.
Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a
solvent system, acrylic resins in a solvent system, in particular in an aqueous system, vinyl
chloride/vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic
solvent systems, butadiene/styrene/acrylonitrile rubbers, drying oils such as linseed oil, resin esters or
modified hardened resins in combination with tar or bitumens, asphalt and epoxy compounds, small
amounts of chlorine rubber, chlorinated polypropylene and vinyl resins.
If appropriate, paints also comprise inorganic pigments, organic pigments or colorants which are
preferably insoluble in salt water. Paints may furthermore comprise materials such as colophonium to
alkw controlled release of the active compounds. Furthermore, the paints may comprise plasticizers,
modifiers which affect the rheological properties and other conventional constituents. The
compounds according to the invention or the abovementioned mixtures may also be incorporated into
self-polishing antifouling systems.
The active compounds according to the invention are also suitable for controlling animal pests, in
particular bisects, 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 spp.,
Dermanyssus gallinae, Glyciphagus domesticus, Oraithodorus moubat, Rhipicephalus sanguineus,
Trombicula atfreddugesi, 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, Gebphilus 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 Coleptera, for example, Anthrenus spp., Attagenus spp., Dermestes spp.,
Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizoperiha 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 caloitrans, 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, Tonga 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 oapitis, Pediculus humanus
corporis, 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 acid esters, carbamates, pyrethroids, growth regulators or active
compounds from other known classes of insecticides.
They are used as 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 mom gels, as
granules or dusts, in baits for spreading or in bah stations.
The preparation and use of the substances according to the invention are illustrated by the examples
below.
rreparauun
Example 1
Synthesis of 4-(l-difluororaethyl-2-trifluoro-ethyi)-2-methyl-phenylamine
Step 1: 4-(l-Dijluoromethyl-l, 2,2,2-tetrqfluoro-ethyl)-2-methyl-phenylamiw
14.0 g (41.66 mraol) 4-[l-(bromo-difluoro-methyl)-l)232-tetrafluoro-ethyl]-2-methyl-phenylamine
was solved in 250 ml toluene, 0.68 g (4.17 mmol) a,a'-azo-bis-isobutyronitrile and 18.2 g (62.49
mmol) tributyl-stannane were added and the mixture was refluxed for 30 minutes. The solvent was
removed under reduced pressure and the residue solved in te/t-butyl-methyl ether. A concentrated
solution of potassium fluoride was added and the mixture was stirred for 2 hours. The organic layer
was separated, washed with a saturated sodium chloride solution, dried with sodium sulphate and
concentrated in vacuo. The crude residue was further purified by column chromatography with
dichloromethane as solvent to obtain the product as a yellow oil.
Yield: 7.8 g (69.2 %)
HPLC:logP(pH 2.3) = 2.74
Step2:4-(l-Difluoromethyl-2,2,2-trifluoro-ethyl)-2-methyl-phenylamine
3.1 g (12.05 mmol) 4-(l-difluoromethyl-l,2,232-tetrafluoro-ethyl)-2-methyl-phenylamine was added
under argon to a mixture of 0.547 g (14.47 mmol) sodium borohydride hi 10 ml dimethyl sulphoxide
and stirred at 50°C for 30 minutes. Water was added and the mixture was extracted twice with tertbulyl-
methyl ether. The combined organic layers were washed with water and a saturated sodium
chloride solution, dried with sodium sulphate and the solvent was removed in vacuo to obtain a
yellow oil.
Yield: 1.2 g (41.6%)
HPLC:logP(pH 2.3) = 2.02
gynthesis of JV1-f4-(2-bromo-1.2t2-trifluoro-l-trifluorometfavl-ethvr)-2-methyl-phenvIl-3-iodo-
JVV2-methanesulfonYl-fSVl-methvl-etfavn-phthalamSde
H3C
Step J: 3-Iodo-N-(l-methyl-2-methylsidfanyl-ethyl)-phthalamic acid
34.73 g (126.74 mmol) 3-iodo-phthalic acid anhydride was solved in N,N-dimethyl-acetamide and at
10°C a solution of 16.0 g (152.10 mmol) (S>l-methyl-2-methylsulfanyl-ethylamine in N,Ndimethyl-
acetamide was added over 60 minutes. The mixture was stirred for further 60 minutes, a
solution of 16.5g (164.76 mmol) sodium hydroxide in water was added over 70 minutes and stirred
for 12 hours. The solvent was removed under reduced pressure and the residue diluted with water.
tert-Butyl-methyl ether was added to the solution and the mixture was acidified with hydrochloric
acid until pH = 1-2, The organic layer was separated, washed with water and a saturated sodium
chloride solution and dried with sodium sulphate. After removing of the solvent in vacuo the product
was obtained in form of an orange oil which crystallizes within a few hours.
Yield: 22.3 g (46.4 %)
Mp.: 132-134°C
Step 2: 4-Iodo-3-{(S)-l-methyl-2-mettylsiilfanyl-ethylimiru3]-3H-isobenz
15.1 g (38.82 mmol) 3-iodo-N-[(S)-l-methyl-2-methylsulfanyl-ethyI]-phthalamic acid was solved in
dichloromethane and 6.02 g (71.67 mmol) sodium hydrogen carbonate in water was added at 40°C
and at the same temperature 5.64 g ( 59.73 mmol) methyl chloroformate over 15 minutes. The mixture
was stirred at 50°C for 1 hour and diluted with water. The organic layer was separated and extracted
two times with dichloromethane. The combined organic phases were washed with water, dried
with sodium sulphate and the solvent was removed in vacuo. The yellow oil crystallizes within a few
hours.
Yield: 10.5 g (69.4%)
HPLC:logP(pH 2.3) = 3.87
[(S)-l-methyl-2-methylsulfanyl-ethyl]-phthalamide (Compound 9 in Table 1)
845.9 mg (2.52 mmol) 4-[l-(bromo-difluoro-methyl)-l,2-tetrafluoro-ethyl]-2-methyl-phenylamine
was solved in dichloroethane, catalytic amounts of concentrated hydrochloric acid were added
and the mixture was heated to 55°C. At this temperature a solution of l.Og (2.77 mmol) 4-iodo-3-
[(S)-l-methyl-2-methylsulfanyl-e1hylimino]-3H-isobenzofuran-l-one was added and the mixture was
stirred for 30 minutes at 65°C. The solvent was removed in vacuo and the crude residue was further
purified by column chromatography with dichloromethane as solvent to obtain a white solid.
methanesulfmyl-(S)-l -methyl-ethyl] -phthalamide (Compound 65 in Table 1)
200.0 mg (0.287 mmol) -brorno-ltrifluoro-l-trifluorornethyl-ethyO-rnethyl-phenyy-Siodo-
JV2-[(S)-l-methyl-2-methylsulfanyl-ethyl]-phthalamide was dissolved in dichloroethane and
2.64 mg (0.057 mmol) formic acid and 39.03 mg (0.344 mmol) hydrogen peroxide were added at
60°C. The mixture was stirred at 60°C for 30 minutes. At 50°C 15 ml of a sodium hydrogen sulfite
solution (10 %) were added and the mixture stirred for 10 minutes. The organic layer was separated,
dried with sodium sulphate and the solvent removed under reduced pressure. The crude product was
further purified by column chromatography with ethylacetate/tert-buryJ-methyl-ether/methanol
(80: 15:5) as solvent.
Yield: 150 mg (73.3%)
Mp.: 120°C
Step 5: -[4-(2-Bromo-l,2,2-trifluoro-l^Mfluoromethyl-ethyl)-2-methyl-phenyl]-3-iod
thanesulfonyl-(S)-l-methyl-ethylJ-phthalamide (Compound 19 in Table 1)
400.0 mg (0.574 mmol) //-[4-(2-Bromo-l,2,2-trifluoro-l-trifluoromethyl-ethyl)-2-rnethyl-phenyl]-3-
iodo-A^-[2-methanesulf5nyl-(S)-l-methyl-ethyl]-phthalamide was dissolved in dichloroethane and
26.4 mg (0.574 mmol) formic acid, 11. 25 rag (0.115 mmol) sulphuric acid and 126.6 mg
(1.434 mmol) hydrogen peroxide were added at 60°C. The mixture was stirred at 60°C for 30
minutes. At 50"C 15 ml of a sodium hydrogen sulphite solution (10 %) were added and stirred for 10
minutes. The organic layer was separated, dried with sodium sulphate and the solvent removed under
reduced pressure. The crude product was former purified by column chromatography with
cyclohexan/ethylacetate 2:1,
Yield: 270 mg (62.0%)
Mp.: 128°C
Diabrotica balteata test (larvae in soil)
Critical concentration test/soil insects - treatment of transgenic plants
Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alky laryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed
with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is
diluted with water to the desired concentration.
The preparation of active compound is poured onto the soil. Here, the concentration of active
compound in the preparation is virtually irrelevant, only the amount by weight of active compound
per volume unit of soil, which is stated hi ppm (mg/1), matters. The soil is filled into 0,251 pots and
these are allowed to stand at 20°C.
Immediately after preparation, 5 pre-germinated maize corns of the cultivar YIELD GUARD (trade
mark of Monsanto Comp., USA) are placed into each pot. After 2 days, the test insects in question are
placed into the treated soil. After a further 7 days, the efficacy of the active compound is determined
by counting the maize plants that have emerged (1 plant = 20% efficacy).
(Table Removed) Example L
Heliothis virescens test (treatment of transgenic plants)
Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
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 stated amount of emulsifier, and the concentrate is diluted
with water to the desired concentration.
Soybean shoots (Glycine max) of the cultivar Roundup Ready (trade mark of Monsanto Comp. USA)
are treated by being dipped into the preparation of active compound of the desired concentration and
are populated with the tobacco bollworm Heliothis virescens while the leaves are still moist
After the desired period of time, the kill in % is determined. 100% means that all caterpillars have
been killed; 0% means that none of the caterpillars have been killed.




WE CLAIM:
1. Optically active phthalamides of the formula (I)
(Formula Removed)
A represents hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl,C1-C6-alkoxy-C1-
C4-alkyl, C1-C6-alkylthio-C1-C4-alkyl, C1-C6-alky1sulfinyl-C1-C4-alkyl, (C1-C6-alkyl)-carbamoyl,
q represents 0,1 or 2,
R1 represents hydrogen or C1-C6-alkyl,
R2 represents hydrogen or C1-C6-alkyl,
Z represents CY4
E1 represents hydrogen or bromine,
E2 represents hydrogen or fluorine,
X1, X2, X3, X4 independently represent hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, nitro, cyano, C1-C6-alkylsulfonyloxy, C1-C6-haloalkylsulfonyloxy, phenylsulfonyl-oxy, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfo-nyl-C1-C6-alkyl, C1-C6-alkylsulfonylamino, bis(C1-C6-aIkylsulfonyl)amino or C1-C6-alkylcarbonyloxy,
Y1, Y2, Y3, Y4 independently represent hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio or cyano.
2. Optically active phthalamides of the formula (I) as claimed in claim 1, in which
A represents hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, the
isomeric pentyls, the isomeric hexyls, ailyl, butenyl, pentenyl, hexenyl, propargyl,
butynyl, pentynyl, hexynyl, C1-C4-alkoxy-C1-C2-alkyl, C1-C4-alkylthio-C1-C2-alkyl,
C1-C4-alkylsulfinyl-C1-C2-alkyl, (C1-C4-alkyl)carbamoyl,
q represents 0, 1 or 2,
R1 represents hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl,
R2 represents hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl,
Z represents CY4
E1 represents hydrogen or bromine

E2 represents hydrogen or fluorine,
X1, X2, X3, X4 independently represent hydrogen, fluorine, chlorine, bromine, iodine, C1-C4-alkyl, C1-C4-haloalkyl, nitro, cyano, C1-C4-alkylsulfonyloxy, C1-C4-haloalkylsulfo-nyloxy, phenylsulfonyloxy, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkylsulfinyl-C1-C4-alkyl, C1-C4-alkylsulfonyl-C1-C4-aIkyl, C1-C4-alkylsulfonylamino, bis(C1-C4-alkyl-suIfonyl)amino or C1-C4-alkylcarbonyloxy,
Y1, Y2, Y3, Y4 independently represent hydrogen, fluorine, chlorine, bromine, iodine, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-halo-alkylthio or cyano.
3. Compounds of formula (I) as claimed in claim 1 as and when used as pesticides by mixing compound of formula (I) with extenders and/or surfactants.

Documents:

1434-DELNP-2007-Abstract-(09-09-2011).pdf

1434-delnp-2007-abstract.pdf

1434-DELNP-2007-Claims-(09-09-2011).pdf

1434-delnp-2007-claims.pdf

1434-DELNP-2007-Correspondence Others-(09-09-2011).pdf

1434-DELNP-2007-Correspondence-Others.pdf

1434-delnp-2007-description (complete).pdf

1434-DELNP-2007-Form-1-(09-09-2011).pdf

1434-delnp-2007-form-1.pdf

1434-DELNP-2007-Form-2-(09-09-2011).pdf

1434-delnp-2007-form-2.pdf

1434-DELNP-2007-Form-3-(09-09-2011).pdf

1434-DELNP-2007-Form-3.pdf

1434-delnp-2007-form-5.pdf

1434-DELNP-2007-GPA-(09-09-2011).pdf

1434-delnp-2007-gpa.pdf

1434-delnp-2007-pct-101.pdf

1434-delnp-2007-pct-210.pdf

1434-delnp-2007-pct-notification.pdf

1434-DELNP-2007-Petition-137-(09-09-2011).pdf

abstract.jpg


Patent Number 251118
Indian Patent Application Number 1434/DELNP/2007
PG Journal Number 09/2012
Publication Date 02-Mar-2012
Grant Date 24-Feb-2012
Date of Filing 22-Feb-2007
Name of Patentee BAYER CROPSCIENCE AG
Applicant Address ALFRED-NOBEL-STR. 50, 40789 MONHEIM, GERMANY
Inventors:
# Inventor's Name Inventor's Address
1 CHRISTIAN FUNKE ROTHENBERG 75 A, 42799 LEICHLINGEN, GERMANY
2 OLGA MALSAM VOR DEM KLOSTERHOF 19, 51503 ROSRATH, GERMANY
3 PETER LOSEL LOHRSTR. 90 A,51371 LEVERKUSEN-HITDORF, GERMANY
4 ULRICH GORGENS FESTER STRASSE 37, 40882 RATINGEN, GERMANY
5 CHRISTIAN ARNOLD PASTOR-LOH-STR.42,LANGENFELD 40764, GERMANY
6 MASANORI TOHNISHI 1040-1-408, FUKUDA, SAKAI, OSAKA,599-8123, JAPAN
7 MINORU YAMAGUCHI SOUTH-TOWER 405, 1-6, KITANODA, SAKAI, OSAKA 586-0022, JAPAN
8 HIROTO HARAYAMA 5-6-305, HONDA-CHO, KAWACHI-NAGANO, OSAKA,586-0037, JAPAN
9 SHINSUKE FUJIOKA 474-1-103, UWAHARA-CHO,KAWACHI-NAGANO,OSAKA 586-0037,JAPAN
10 RUDIGER FISCHER ZU DEN FUSSFALLEN 23, 50259 PULHEIM, GERMANY
PCT International Classification Number C07C 317/26
PCT International Application Number PCT/EP2005/009018
PCT International Filing date 2005-08-20
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 04020618.7 2004-08-31 EUROPEAN UNION