Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
2001-04-18
2002-10-29
Clardy, S. Mark (Department: 1616)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C504S292000, C514S336000, C514S451000
Reexamination Certificate
active
06472350
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to the use of certain 3-phenyl-pyrones as pesticides, fungicides and herbicides.
BACKGROUND OF THE INVENTION
Numerous oxymethoxy-3-phenyl-pyrone derivatives having pesticidal, fungicidal and herbicidal properties have already been disclosed (cf. WO 97-19 941). The activity of these substances is good; however, at low application rates or at certain indications, it sometimes leaves something to be desired.
Furthermore, 3-(2-methyl-4-fluoro-phenyl)-4-hydroxy-5-methyl-6-(pyrid-2-yl)-pyrone and 3-(2-methyl-4-chloro-phenyl)-4-hydroxy-5-methyl-6-(4-fluoro-phenyl)-pyrone have already been described as intermediates (cf. WO 97-19 941). However, biological properties of these substances have hitherto not been mentioned.
It has now been found that the 3-phenyl-pyrones of the formula
in which
x represents pyrid-2-yl and
Y represents fluorine,
or
x represents 4-fluoro-phenyl and
Y represents chlorine,
are highly suitable for use as pesticides, fungicides and herbicides.
Surprisingly, the 3-phenyl-pyrones to be used according to the invention have a considerably better pesticidal, fungicidal and herbicidal activity than the constitutionally most similar prior-art active compounds of the same direction of action.
SUMMARY OF THE INVENTION
3-(2-methyl4-fluoro-phenyl)4-hydroxy-5-methyl-6-(pyrid-2-yl)-pyrone and 2-(2-methyl4-chloro-phenyl)4-hydroxy-5-methyl-6-(4-fluoro-phenyl)-pyrone are suitable for use as pesticides, fungicides and herbicides.
The 3-phenyl-pyrones of the formula (I) to be used according to the invention can be depicted by the formula
The broken line is meant to indicate that these substances can be present in the two tautomeric forms
The 3-phenyl-pyrones to be used according to the invention can either be present as mixtures of compounds of the formula (I) and (Ia), or else in the form of pure isomers. Mixtures of compounds of the formulae (I) and (Ia) can be separated by physical means, for example by chromatographic methods.
For reasons of clarity, hereinbelow only one of the possible isomers is shown in each case. This does not exclude that the compounds, if appropriate, may be present in the form of the isomer mixtures or in the other isomeric form in question. Specifically, the formula (I) relates to the 3-phenyl-pyrones of the formulae
The 3-phenyl-pyrones of the formula (I) have already been disclosed (cf. WO 97-19 941). They can be prepared by reacting carbonyl compounds of the formula
in which
X is as defined above,
with ketene derivatives of the formula
in which
Y is as defined above and
Hal represents chlorine or bromine,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.
Suitable diluents for carrying out the above process are all customary organic solvents which are inert towards the reactants. Preference is given to using hydrocarbons, such as o-dichlorobenzene, tetraline, toluene and xylene, furthermore ethers, such as dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, moreover polar solvents, such as dimethyl sulphoxide, sulpholane, dimethylformamide or N-methylpyrrolidone.
Suitable acid acceptors for carrying out the above process are all customary acid binders. Preference is given to using tertiary amines, such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN), Huinig base or N,N-dimethylaniline.
When carrying out the above process, the reaction temperatures can be varied within a relatively wide range. The process is expediently carried out at temperatures between 0° C. and 250° C., preferably between 50° C. and 220° C.
The above process is preferably carried out under atmospheric pressure.
When carrying out the above process, generally an equimolar amount of ketene derivative of the formula (III) and, if appropriate, an equimolar amount of acid acceptor are employed per mole of carbonyl compound of the formula (II). However, it is also possible to use a relatively large excess (up to 5 mol) of one or the other component.
The 3-phenyl-pyrones of the formula (I) to be used according to the invention have very good pesticidal activity and are very well tolerated by crop plants.
The active compounds are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which are encountered in agriculture, in forests, in the protection of stored products and of materials, and in the hygiene sector. 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 Isopoda, 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,
Geophilus carpophagus
, Scutigera spec.
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,
Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus
, Gryllotalpa spp.,
Locusta migratoria migratorioides, Melanoplus differentialis
and
Schistocerca gregaria.
From the order of the Dermaptera, for example,
Forficula auricularia.
From the order of the Isoptera, for example, Reticulitermes spp.
From the order of the Anoplura, for example,
Phylloxera vastatrix
, Pemphigus spp.,
Pediculus humanus corporis
, Haematopinus spp. and Linognathus spp.
From the order of the Mallophaga, for example, Trichodectes spp. and Damalinea spp.
From the order of the Thysanoptera, for example,
Frankliniella occidentalis, Hercinothrips femoralis, Thrips palmi
and
Thrips tabaci.
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, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae
, Myzus spp.,
Phorodon humuli, Rhopalosiphum padi
, Empoasca spp.,
Euscelis bilobatus, Nephotettix cincticeps, Lecanium comi, 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 maculipennis, Malacosoma neustria, Euproctis chrysorrhoea
, Lymantria spp.
Bucculatrix thurberiella, Phyllocnistis citrella
, Agrotis spp., Euxoa spp., Feltia spp.,
Earias insulana
, Heliothis spp.,
Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia litura
, Spodoptera spp.,
Trichoplusia ni, Carpocapsa pomonella
, Pieris spp., Chilo spp.,
Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima
and
Tortrix viridana.
From the order of the Coleoptera, for example,
Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae
, Diabrotica spp.,
Psylliodes chrysocephala, Epilachna varivestis
, Atomaria spp.,
Oryzaephilus surinamensis
, Anthonomus spp., Sitophilus spp.,
Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica
, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp.,
Meligethes aeneus
, Ptinus spp.,
Niptus hololeucus, Gibbium psylloides
, Tribolium spp.,
Tenebrio molitor
, Agriotes spp., Conoderus spp.,
Melolontha melolontha, Amphimallon solstitialis
and
Erdelen Christoph
Fischer Reiner
Lieb Folker
Ruther Michael
Bayer Aktiengesellschaft
Clardy S. Mark
Gil Joseph C.
Mrozinski, Jr. John E.
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