• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    The present invention relates to novel tetrahydropyrimidine derivatives of general formula (I), their preparation and their use as pesticides: In this formula, A is the group (Ia) - (CH 2) m-COXR 1 and (Ib) , ≪ / RTI > Het is a heteroatomic ring containing 1, 2, 3 or 4 nitrogen atoms and / or one or two oxygen or sulfur atoms and the number of ring heteroatoms is 1, 2, 3 or 4 and is halogen, cyano , Nitro, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, alkynyl, alkoxy, halogenoalkoxy, alkenyloxy, halogenoalkenyloxy, alkynyloxy, alkylthio, halogenoalkylthio, alkenyl Alkylthio, arylthio, arylthio, haloalkylthio, arylthio, arylthio, arylthio, arylthio, arylthio, arylthio, arylthio, arylthio, arylthio Or a 5-or 6-membered heterocyclic group optionally substituted by one or more substituents selected from the group consisting of amino, aralkyl, formylamino, alkylcarbonylamino, formyl, carbamoyl, alkylcarbonyl and alkoxycarbonyl, R 1 represents hydrogen, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, optionally substituted aralkyl or optionally substituted 5- or 6-membered heterocyclylalkyl, R < 2 > represents optionally substituted alkyl or aralkyl, X represents oxygen, or group -NH- or -N-alkyl-, m represents an integer of 1 to 20, n represents an integer of 0 to 2, However, A represents a group (Ia) Het has Lt; / RTI > R 1 represents hydrogen or ethyl, X represents oxygen, m represents 1 or 2, Compounds in which n represents 0 are excluded.
    公开号:KR19990087152A
    申请号:KR1019980706545
    申请日:1997-02-19
    公开日:1999-12-15
    发明作者:요하네스 카넬라코풀러스；데트레프 볼베버；크리스토프 에르델렌
    申请人:빌프리더 하이더；바이엘 악티엔게젤샤프트；
    IPC主号:
    专利说明:

    Tetrahydropyrimidine derivative
    Especially 6-substituted 6,7-dihydro-8-nitro- (5H) -1- (2- chloropyridin-5-yl-methyl or 2-chloro-1,3-thiazol- ) -Imidazolidino- [2,3-f] -pyrimidines are known to have insecticidal properties (see, for example, EP-A-0 247 477) . However, the activity and action spectrum of these compounds are not always completely satisfactory, especially at low application rates and concentrations.
    The present invention relates to novel tetrahydropyrimidine derivatives, processes for their preparation and their use for the rescue of animal pests.
    The present invention provides novel tetrahydropyrimidine derivatives of general formula (I)

    In this formula,
    A is the group (Ia) - (CH 2) m-COXR 1 and (Ib) , ≪ / RTI >
    Het is a heteroatomic ring containing 1, 2, 3 or 4 nitrogen atoms and / or one or two oxygen or sulfur atoms and the number of ring heteroatoms is 1, 2, 3 or 4 and is halogen, cyano , Nitro, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, alkynyl, alkoxy, halogenoalkoxy, alkenyloxy, halogenoalkenyloxy, alkynyloxy, alkylthio, halogenoalkylthio, alkenyl Alkylthio, arylthio, arylthio, haloalkylthio, arylthio, arylthio, arylthio, arylthio, arylthio, arylthio, arylthio, arylthio, arylthio Or a 5-or 6-membered heterocyclic group optionally substituted by one or more substituents selected from the group consisting of amino, aralkyl, formylamino, alkylcarbonylamino, formyl, carbamoyl, alkylcarbonyl and alkoxycarbonyl,
    R 1 represents hydrogen, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, optionally substituted aralkyl or optionally substituted 5- or 6-membered heterocyclylalkyl,
    R < 2 > represents optionally substituted alkyl or aralkyl,
    X represents oxygen, or group -NH- or -N-alkyl-,
    m represents an integer of 1 to 20,
    n represents an integer of 0 to 2,
    However,
    A represents a group (Ia)
    Het has Lt; / RTI >
    R 1 represents hydrogen or ethyl,
    X represents oxygen,
    m represents 1 or 2,
    Compounds of formula (I) in which n represents 0 are excluded.
    Also, the tetrahydropyrimidine derivative of general formula (I)
    a) dissolving a nitromethylene derivative of the formula (II) in the presence of at least twice the molar amount of formaldehyde, if appropriate in the presence of an acid catalyst and, if appropriate, in the presence of a diluent and if appropriate in the presence of a base, With an amine of formula (IIIa) or (IIIb)
    b) the nitropyrimidine derivative of general formula (IV) is obtained by reacting it with a compound of general formula (V) in the presence of a base and, if appropriate, in the presence of a diluent:

    H 2 N- (CH 2 ) m -CO-X R 1 (IIIa)


    Het-CH 2 -L (V)
    In this formula,
    Het, n, R 1, R 2, X, m, A and n are as defined above,
    L is an anionic leaving group.
    Finally, the novel tetrahydropyrimidine derivatives of the general formula (I) have excellent biological properties and are suitable for the protection of animal pests, in particular for protection of agriculture, forestry, stored products and materials and for insect, spider and nematodes encountered in the field of veterinary medicine , ≪ / RTI >
    The general formula (I) provides a general definition of the tetrahydropyrimidine derivatives according to the invention.
    Preferred substituents or ranges of radicals listed in the above and in the general formulas mentioned below are exemplified:
    Het is preferably selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, nitro, C 1 -C 4 -alkyl (which is optionally substituted by fluorine and / or chlorine), C 2 -C 4 -alkenyl fluorine and / or by chlorine is optionally substituted), C 2 -C 4 - alkynyl, C 1 -C 4 - alkoxy (which is optionally substituted by fluorine and / or chlorine), C 3 -C 4 - alkenyl (Which is optionally substituted by fluorine and / or chlorine), C 3 -C 4 -alkynyloxy, C 1 -C 4 -alkylthio which is optionally substituted by fluorine and / or chlorine, C 3 - C 1 -C 4 -alkynylthio, which is optionally substituted by fluorine and / or chlorine, C 3 -C 4 -alkynylthio, C 1 -C 4 -alkylsulfinyl, which is optionally substituted by fluorine and / or chlorine, C 1 -C 4 -alkylsulfonyl which is optionally substituted by fluorine and / or chlorine, amino, C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) -amino , Phenyl, phenoxy, phenylthio, phenyla No, benzyl, formylamino, C 1 -C 4 - into carbonyl-alkyl, amino-carbonyl, formyl, carbamoyl, C 1 -C 4 -alkyl-carbonyl and / or C 1 -C 4 - alkoxy Thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3- or 1,2,4-triazolyl optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of hydrogen, Oxazolyl, isoxazolyl, 1,2,4- or 1,3,4-oxadiazolyl, thiazolyl, isothiazolyl, 1,2,3-, 1,2,4-, 1,2,5 - or a 5- or 6-membered group selected from the group consisting of 1,3,4-thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl and pyrazinyl.
    R 1 is preferably hydrogen, C 1 -C 12 -alkyl, C 1 -C 6 -halogenoalkyl, C 2 -C 6 -alkenyl, or C 2 -C 6 -halogenoalkenyl, or one 5 to the same or by different substituents optionally substituted phenyl -C 1 -C 4 - represents alkyl, suitable phenyl substituents are halogen, cyano, nitro, C 1 -C 4 - alkyl, C 1 -C 4 - alkoxy , C 1 -C 4 -alkylthio, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -halogenoalkoxy, C 1 -C 4 -halogenoalkylthio, C 1 -C 4 -alkoxycarbonyl , amino, C 1 -C 4 - alkylaminocarbonyl or di - (C 1 -C 4 - alkyl) -amino, or;
    5-or 6-membered heterocyclyl-C 1 -C 4 -alkyl optionally substituted by one to three identical or different substituents, each of which is optionally substituted by fluorine, chlorine, bromine, iodine, cyano, Nitro, C 1 -C 4 -alkyl which is optionally substituted by fluorine and / or chlorine, C 2 -C 4 -alkenyl which is optionally substituted by fluorine and / or chlorine, C 2 -C 4 - alkynyl, C 1 -C 4 - alkoxy (which is optionally substituted by fluorine and / or chlorine), C 3 -C 4 - alkenyloxy (which is optionally substituted by fluorine and / or chlorine), C 3 -C 4 - alkynyloxy, C 1 -C 4 - alkylthio (which is optionally substituted by fluorine and / or chlorine), C 3 -C 4 - alkenyl, alkylthio (which is optionally substituted by fluorine and / or chlorine, is), C 3 -C 4 - alkynyl, thio, C 1 -C 4 - alkylsulfinyl (which is optionally substituted by fluorine and / or chlorine), C 1 -C 4 - alkylsulfonyl (which is fluorine and / In addition Is optionally substituted by chlorine, amino, C 1 -C 4 -alkylamino, di- (C 1 -C 4 -alkyl) -amino, phenyl, phenoxy, phenylthio, phenylamino, benzyl, formylamino Identical or different, selected from the group consisting of C 1 -C 4 -alkyl, carbonylamino, formyl, carbamoyl, C 1 -C 4 -alkyl-carbonyl and / or C 1 -C 4 -alkoxy-carbonyl or Thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3- or 1,2,4-triazolyl, oxazolyl, isoxazolyl, 1, 2- or 4-thiazolyl optionally mono- to trisubstituted by different substituents, 2,4- or 1,3,4-oxadiazolyl, thiazolyl, isothiazolyl, 1,2,3-, 1,2,4-, 1,2,5- or 1,3,4-thia Is selected from the group consisting of pyridyl, pyridazinyl, pyrimidinyl and pyrazinyl.
    R 2 preferably represents C 1 -C 8 -alkyl or optionally substituted benzyl.
    X preferably represents oxygen, or a group -NH- or -N- (C 1 -C 8 -alkyl) -.
    and m is preferably an integer of 1 to 12.
    n is preferably a number of 0 or 1.
    At the same time
    A represents a group (Ia)
    Het has Lt; / RTI >
    R 1 represents hydrogen or ethyl,
    X represents oxygen,
    m represents 1 or 2,
    Compounds of formula (I) in which n represents 0 are excluded.
    Het is particularly preferably each independently selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, nitro, C 1 -C 2 -alkyl which is optionally substituted by fluorine and / or chlorine, C 1 -C 2 -alkoxy (Which is optionally substituted by fluorine and / or chlorine), C 1 -C 2 -alkylthio which is optionally substituted by fluorine and / or chlorine and C 1 -C 2 -alkylsulfonyl which is fluorine and / or chlorine Which is optionally mono- to trisubstituted by the same or different substituents selected from the group consisting of lower alkyl, lower alkoxy, lower alkoxy, lower alkoxy, lower alkoxy, lower alkoxy, , Or a 5- or 6-membered heterocyclic group selected from the group consisting of 1,2,5-thiadiazolyl, pyridyl, pyrazinyl and pyrimidinyl.
    R 1 is particularly preferably hydrogen, C 1 -C 8 -alkyl, C 1 -C 4 -halogenoalkyl, C 2 -C 4 -alkenyl, or C 2 -C 4 -halogenoalkenyl, or 1 Phenyl-C 1 -C 2 -alkyl optionally substituted by one to three identical or different substituents selected from fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, Trifluoromethyl, trifluoromethoxy, and trifluoromethylthio; or R < 3 > 5-or 6-membered heterocycle-C 1 -C 2 -alkyl optionally substituted by one to three identical or different substituents, each heterocyclic group is optionally substituted with one or more substituents independently selected from the group consisting of fluorine, chlorine, bromine, cyano, C 1 -C 2 -alkyl which is optionally substituted by fluorine and / or chlorine, C 1 -C 2 -alkoxy which is optionally substituted by fluorine and / or chlorine, C 1 -C 2 -alkylthio (Which is optionally substituted by fluorine and / or chlorine), or C 1 -C 2 -alkylsulfonyl which is optionally substituted by fluorine and / or chlorine, 1,2,4 Thiazolyl, isoxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrazinyl and pyrimidinyl.
    R 2 is particularly preferably C 1 -C 4 -alkyl or halogen (chlorine, fluorine, bromine), C 1 -C 4 -alkyl, C 1 -C 2 -alkoxy, C 1 -C 2 -alkylthio, C 1 -C 2 -halogenoalkyl, C 1 -C 2 -halogenoalkoxy, C 1 -C 2 -halogenoalkylthio, nitro or cyano.
    X is particularly preferably oxygen, or the group -NH-, -N (CH 3) - or -N (C 2 H 5) - represents a.
    and m is particularly preferably an integer of 1 to 10.
    n is particularly preferably a number of 0 or 1.
    At the same time
    A represents a group (Ia)
    Het has Lt; / RTI >
    R 1 represents hydrogen or ethyl,
    X represents oxygen,
    m represents 1 or 2,
    Compounds in which n is 0 are excluded.
    Het very particularly preferably represents pyridyl or thiazolyl optionally substituted by one or two identical or different substituents each selected from the group consisting of fluorine, chlorine and bromine.
    R 1 very particularly preferably denotes hydrogen, C 1 -C 8 -alkyl or benzyl optionally substituted by one or two identical or different substituents, suitable substituents being fluorine, chlorine, bromine, cyano, nitro, Methyl, ethyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio; Are each pyridylmethyl or thiazolylmethyl optionally substituted by one or two identical or different substituents selected from the group consisting of fluorine, chlorine and bromine.
    R 2 very particularly preferably represents C 1 -C 4 -alkyl or benzyl.
    X very particularly preferably represents an oxygen or -NH- group.
    m is very particularly preferably an integer of 1 to 8,
    n is very particularly preferably a number of 0 or 1.
    At the same time
    A represents a group (Ia)
    Het has Lt; / RTI >
    R 1 represents hydrogen or ethyl,
    X represents oxygen,
    m represents 1 or 2,
    Compounds in which n is 0 are excluded.
    The above-mentioned general or preferred definitions or examples of radicals apply to the final product and accordingly to the starting materials and intermediates. These radical definitions can be combined with each other as desired, i.e. a combination between the respective preferred ranges is also possible.
    Preferred according to the invention are those compounds of general formula (I) which contain a combination of the definitions given above as being preferred.
    Particularly preferred according to the invention are particularly preferred compounds of formula (I) containing a combination of the definitions given above.
    Very particularly preferred according to the invention are the compounds of formula (I) which contain a combination of the definitions given above very particularly preferably.
    In the radical definitions given above and below, hydrocarbon radicals such as alkyl or alkenyl are also associated in each case with heteroatoms, such as alkoxy or alkylthio, which are as straight or branched as possible.
    Preferred compounds according to the invention are the compounds of the formulas (Ic) to (If)




    In this formula,
    Het < 1 > represents optionally substituted pyridyl,
    Het < 2 > represents an optionally substituted thiazolyl,
    A is as defined in the definition of the present invention.
    Preferred compounds according to the invention are also the substance groups of the general formulas (Ia-1), (Ib-1), (Ic-1) and (Id-1)




    In this formula,
    A is generally preferred, particularly preferred and very particularly preferred as defined above.
    For example, the method (a) according to the present invention can be carried out in the presence of a catalyst such as 3- (2-chloropyridin-5-yl-methyl) -2-nitromethylene-imidazolidine, methylglycinate hydrochloride and 2 mol of formaldehyde, , The reaction scheme can be illustrated by the following scheme: < RTI ID = 0.0 >

    For example, 6,7-dihydro-6-methoxycarbonylmethyl-8-nitro- (5H) -imidazolidino- [2,3- f] -pyrimidine and 2-chloro- If methyl-pyridine is used to carry out the process (b) according to the invention, the reaction process can be illustrated by the following scheme

    The nitromethylene derivatives of the general formula (II) used as starting materials according to the invention are known (see for example EP-A 0 163 855, EP-A 0 192 060, EP-A 0 247 477, EP- A 0 316 843 and EP-A 0 316 845) and / or can be prepared by known methods (cf.
    If the nitromethylene derivative is used in the form of a hydrohalide, its hydrochloride is preferred.
    The amines of the formulas (III-a) and (III-b) which are also used as starting materials in the process (a) according to the invention are generally known compounds of organic chemistry and / or can be obtained by conventional methods.
    No nitropyrimidine derivatives of the general formula (IV) used as starting materials in the process (b) according to the present invention are disclosed. These are obtained by reacting a nitromethylene derivative of general formula (IIa) (cf. for example EP-A 0 247 477) with an amine of general formula (III-a) or (III-b) can do:

    In this formula,
    n is as defined above.
    Compounds further used as starting materials in process (b) according to the invention are generally defined by the general formula (V). L preferably represents chlorine, bromine, iodine, acetoxy, tosyl or mesyl. Compounds of general formula (V) are generally known materials of organic chemistry.
    The process (a) according to the invention is preferably carried out using a diluent. Suitable diluents are water and organic solvents which are inert in the reaction. These are preferably aliphatic and aromatic compounds and optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzene, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, Chlorobenzene and o-dichlorobenzene, ethers such as diethyl ether and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, alcohols such as methanol, ethanol, n-propanol and n- Isopropanol. Preferably a mixture of alcohol and water is used.
    The process (a) according to the process is carried out, if appropriate, in the presence of an acidic, non-oxidizing catalyst. Hydrohalic acids such as hydrochloric acid and hydrobromic acid, phosphoric acid and lower carboxylic acids such as acetic acid and propionic acid are particularly useful.
    The reaction temperature of process (a) according to the invention can vary over a relatively wide range. Generally, the process is carried out at a temperature of -20 ° C and + 120 ° C, preferably 0 ° C to + 80 ° C.
    The process (a) according to the invention is generally carried out under atmospheric pressure. However, it is also possible to carry out under pressure or reduced pressure.
    In carrying out the process (a) according to the invention, from 1 to 1.5 mol, preferably from 1 to 1.2 mol, of an amine of the general formula (III) and from 2 to 4 mol, preferably from 2 to 3 mol, of formaldehyde Is used per 1 mole of the nitromethylene derivative of the general formula (II).
    The amine of general formula (III) can be used as an aqueous solution if appropriate. If gaseous amines of the general formula (III) are used, they can be passed through a mixture of a diluent, a compound of the general formula (II) and formaldehyde. In the process according to the invention, formaldehyde is used as an aqueous solution. The reaction is generally carried out in a suitable diluent and the reaction mixture is stirred for several hours at the temperature required in each case. The post-treatment in the process according to the invention is carried out in the usual way in each case.
    The process (b) according to the invention is preferably carried out using a diluent. Suitable diluents are substantially all inert organic solvents. These are in particular aliphatic and aromatic compounds, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzene, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, And o-dichlorobenzene, ethers such as diethyl ether and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl ketone or methyl isopropyl ketone Or methyl isobutyl ketone, esters such as methyl acetate or ethyl acetate, nitriles such as acetonitrile or propionitrile, amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone, and Also, dimethyl sulfoxide, tetramethylene sulfone or hexa Butyl phosphine is porik tree amide.
    Suitable bases in methods (a) and (b) according to the present invention are all acid binders commonly used in such reactions. Preferred are alkali metal hydrides and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride or calcium hydride, alkali metal or alkaline earth metal hydroxides, such as lithium hydroxide Sodium hydroxide, potassium hydroxide or calcium hydroxide, alkali metal carbonates or hydrogencarbonates or alkali metal carbonates or hydrogencarbonates such as sodium carbonate or hydrogencarbonate or potassium carbonate or hydrogencarbonate or calcium Carbonates, alkali metal acetates such as sodium acetate or potassium acetate, alkali metal alkoxides such as sodium tert-butoxide or potassium tert- And also basic nitrogen compounds such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine, N, N Dimethylbenzylamine, N, N-dimethyl-aniline, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6- Methyl- pyridine, 1,5-diazabicyclo [4.3.0] -non-5-ene (DBN), 1,8-diazabicyclo- [5.4.0 ] Undec-7-ene (DBU) or 1,4-diazabicyclo- [2.2.2] -octane (DABCO).
    The reaction temperature in process (b) according to the invention can vary over a relatively wide range. In general, the reaction is carried out at a temperature of from 0 캜 to 100 캜, preferably from 10 캜 to 80 캜.
    The process (b) according to the invention is generally carried out at atmospheric pressure. However, it is also possible to carry out under pressure increasing and pressure reducing.
    The starting materials required to carry out process (b) according to the invention are generally used in approximately equimolar amounts. However, it is also possible to use relatively high amounts of one of the two components used in each case. The reaction is generally carried out in the presence of an acid acceptor in a suitable diluent and the reaction mixture is stirred for several hours at the temperature required in each case. The post-treatment is carried out in a conventional manner.
    The active compounds are suitable for the remediation of insects, arachnids and nematodes encountered in the protection and sanitary areas of animal pests, in particular agriculture, forestry, storage products and materials, and have good plant tolerance and low toxicity to warm-blooded animals . They can preferably be used as crop protection agents. The active compound is active for all or some stages of species and metamorphism that are normally sensitive or resistant. The above-mentioned pests include the following:
    Isopoda, for example Oniscus asellus, Armadillidium vulgare, and Porcellio scaber.
    Diplopoda neck, for example Blaniulus guttulatus.
    Chilopoda necks, for example Geophilus carpophagus and Scutigera spec.
    A neck of Symphyla, for example Scutigerella immaculata.
    Thysanura neck, for example Lepisma saccharina.
    Collembola neck, for example Onychiurus armatus.
    Such as Orthoptera sp., Such as Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, But are not limited to, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistoser < RTI ID = 0.0 > Schistocerca gregaria.
    Dermaptera neck, for example Forficula auricularia.
    Isoptera, for example, Reticulitermes spp.
    Anoplura, for example Pediculus humanus corporis, Haematopinus spp. And Linognathus spp., Can be used for the treatment of the disease.
    Mallophaga necks, for example Trichodectes spp. And Damalinea spp.
    Thysanoptera species, for example, Hercinothrips femoralis and Thrips tabaci.
    Heteroptera spp., For example Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rodney < RTI ID = 0.0 > Rhodnius prolixus and Triatoma spp.
    For example, a species of Homoptera such as Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundin, Such as Hyalopterus arundinis, Phylloxera vastrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon spp. humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, ), Saisetia olera (Saissetia ol eae), Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudo koji, Pseudococcus spp. And Psylla spp.
    Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, For example, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp. , Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Echinochloa spp. Such as Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodoptera exigua, Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo sp. Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pelionella, For example, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, and Tortrix viridana.
    Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, and the like. , Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., And the like. Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthomonas spp., Pseudomonas spp. Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchu sp. s assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp. ), Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides (Gibbium psylloides, ), Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis and Costelytra zealandica.
    Hymenopera sp., For example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp. Vespa spp.).
    Diptera spp., For example Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Muscat spp. Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp. , Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., And the like. Such as Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomia ahiossiami Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, and Tipula paludosa.
    Siphonaptera, for example, Xenopsylla cheopis and Ceratophyllus spp.
    Arachnida spp., For example Scorpio maurus, Latrodectus mactans.
    Acarina necks, such as Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophis ribis, Such as 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., And Tetranychus spp.).
    Plant parasitic nematodes include, but are not limited to, Pratylenchus spp., Radopholus similis, Ditylenchus dipsasi, Tylenchulus semipenetrans, Heterodera spp. Such as Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp. (Xiphinema spp.), And Trichodorus spp.
    The active compounds of the general formula (I) of the present invention have particularly excellent pesticidal activity.
    These include, in particular, plant-damaging insects, for example, larvae of the order Phaedon cochlaeriae, insects of the Plutella maculipennis, insects of the green rice cicada (Nephotettix cinctriceps) and owl moth Spodoptera frugiperda), or peach leaf aphids (Myzus percicae).
    The active compounds may be in the form of solutions, emulsions, hydratable powders, suspensions, powders, powders, pastes, soluble powders, granules, suspensions, emulsion concentrates, natural and synthetic materials impregnated with active compounds, It can be converted into a conventional preparation.
    These formulations are prepared in a known manner, for example by mixing the active compounds with extenders, i. E. Liquid solvents and / or solid carriers, optionally using surfactants, i.e. emulsifiers and / or dispersants and / or foam- .
    When water is used as an extender, for example, an organic solvent can also be used as an auxiliary solvent. As liquid solvents there may be mentioned aromatic compounds such as xylene, toluene or alkylnaphthalene, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride, cyclohexane or paraffins such as mineral oil fractions, mineral oils and vegetable oils Alcohols such as aliphatic hydrocarbons, butanol or glycols and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl formamide and dimethyl sulfoxide, Do.
    Solid carriers include, for example, ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly disperse silicas, alumina and silicates Is appropriate. Solid carriers for granules include, for example, granulated and classified natural rocks such as calcite, marble, pumice, hemastone and dolomite, and synthetic granules of inorganic and organic powders, and organics such as sawdust, coconut shells, cornstalks and tobacco stalks. Granules of the material are suitable. Emulsifiers and / or foam-formers include, for example, nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers such as alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl Sulfonates and protein hydrolysis products are suitable. As the dispersing agent, for example, lignin-sulfite waste liquid and methyl cellulose are suitable.
    Natural and synthetic polymers in the form of powders, granules or emulsions such as, for example, carboxymethylcellulose, gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids such as cephalin and lecithin, and synthetic phosphatides, . As other additives, mineral oil and vegetable oil may be used.
    Inorganic pigments such as iron oxide, titanium oxide and prussian blue and coloring agents such as organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes and micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc May be used.
    The preparations generally contain from 0.1 to 95% by weight, preferably from 0.5 to 90% by weight, of the active compound.
    The active compounds according to the present invention may be formulated into commercially available preparations as a mixture with other active compounds such as insecticides, attractants, sterilizing agents, fungicides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides, And may be in the form of use made from the preparation. Pesticides include in particular, for example, phosphates, carbamates, carboxylates, chlorinated hydrocarbons, phenylureas and substances produced by microorganisms and the like.
    Examples of components which are particularly advantageous for the mixtures are:
    Fungicide:
    2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-1,3-thiazole-5-carboxyanilide; 2,6-dichloro-N- (4-trifluoromethylbenzyl) -benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) -acetamide; 8-hydroxyquinoline sulfate; Methyl (E) -2- {2- [6- (2-cyanophenoxy) -pyrimidin-4-yloxy] -phenyl} -3-methoxyacrylate; Methyl (E) -methoximino [alpha - (o-tolyloxy) -o-tolyl] acetate; But are not limited to, 2-phenylphenol (OPP), aldimorph, amipropos, anilazine, azaconazole, benzalacyl, benodanil, benomyl, binaparyl, biphenyl, bitterthanol, But are not limited to, bromomonasol, bupyrimate, butothiobate, calcium polysulfide, captapol, mercaptans, carbendazim, carboxyne, quinomethionate, chlornev, chloropicrin, chlorothalonil, czulolinate, But are not limited to, cymoxanil, cyprocannazole, cyprofuran, dichlorophen, diclobutrazole, diclofenanide, dichloromethane, dichlororan, diethophenecarb, diphenococonazole, dimethyimol, dimethomorph , Dinonocazole, dinocap, diphenylamine, dipyrithione, ditaliphose, dithianone, dodine, Draisonolone, ediphenose, epoxiconazole, ethidimol, etidiazole, Naphthol, naphthol, naphthol, phenol, phenanthroline, phenclodonyl, phenpropidine, But are not limited to, thiourea, tartrate, pentyne hydroxide, per night, perimin, fluorine, fluoride, fluorimide, But are not limited to, aluminum, phthalide, fueridazole, furalacox, furmacrox, guazatine, hexachlorobenzene, hexaconazole, Copper iodide, copper chloride, oxycarbide and Bordeaux mixture, mancofer, mancozebe, iodine, copper, copper, , Mannob, mephanipyrim, mepronil, methacalpocarb, metconazole, metasulfocarb, metoproxam, methiram, metsulfoxane, Michaelobutanyl, nickel dimethyldithiocarbamate, Isopropyl, norarimol, opulac, oxadic But are not limited to, polyvinylpyrrolidone, polyvinylpyrrolidone, polyvinylpyrrolidone, polyvinylpyrrolidone, polyvinylpyrrolidone, polyvinylpyrrolidone, polyvinylpyrrolidone, polyvinylpyrrolidone, polyvinylpyrrolidone, Pyrimethanil, pyroquilon, quintogen (PCNB), sulfur and sulfur preparations, tebuconazole, teclophthalam, tetracycline, Thiophene-methyl, thiam, tolclofos-methyl, tolyl fl uanide, triadimefon, triadimenol, triazide, triclamide, Triacylglycerol, triacylglycerol, triacylglycerol, triacylglycerol, triacylglycerol, triacylglycerol, triacylglycerol, triacylglycerol,
    Live bacterial agent:
    Hydroxypentyl, nickel dimethyldithiocarbamate, carzymycin, octylrionone, furancarboxylic acid, oxytetracycline, provenazole, streptomycin, teclophthalimide, copper sulfate and other copper formulations.
    Pesticides / acaricides / nematocides:
    Azamycin, Azamycin, Azamycin, Abamectin, AC 303 630, Acetate, Acrinatrine, Allanicab, Aldicarb, Alphametriene, Amitraz, Abermectin, AZ 60541, Azadirachtin, Cyclotin, Bacillus thuringiensis, Bendiocarb, Bupulacarb, Benlett, Beta-Siflutrin, Bifenthrin, BPMC, Bropfenprox, Bromophor A, Bupencab, Bupropezin, Carboplatin, carbofenone, carbosulfan, carotene, CGA 157419, CGA 184699, chloetocarb, chlorethoxyphosphorus, chlorphenvinphosphorus, chlorofluorescent, chloromethylphosphoric acid, The present invention relates to the use of a compound of formula (I) or a pharmaceutically acceptable salt thereof as an active ingredient in the manufacture of a medicament for the treatment and / or prevention of cancer, including, but not limited to, corticosteroids, Margine, deltamethrin, demethon-M, demethon-S, demethon-S-methyl, Diethionone, dithionone, dichlopenthone, dichlorobos, dicliphorus, dichotorousus, diethion, diplubenzuron, dimethoate, dimethylbinphosphine, dioxathione, But are not limited to, but are not limited to, but are not limited to, but are not limited to, but are not limited to, camptothecin, camptothecin, camptothecin, camptothecin, camptothecin, camptothecin, camptothecin, camptothecin camptothecin, camptothecin camptothecin, camptothecin camptothecin camptothecin camptothecin camptothecin camptothecin camptothecin camptothecin camptothecin camptothecin , Phenoxycarb, fenproparin, fenpyrad, penicloximate, fention, fenvalerate, fipronil, furosine, flucyclovsulone, flucentrinate, flupenoxolone, flupenprox , Fluorovanate, phonophos, formothion, postazite, puibenpuprox, furathiocarb, HCH, heptenophores, hexaflumuron, hecityas, imidacloprid, , Isopenpose, isoprocarb, isoxathion, ibex But are not limited to, tin, lambda-cyhalothrin, rufenuron, malathion, mecharbam, mebinfos, mesulfenp, methaldheid, methacryphos, methamidopos, methidathion, methiocarb, Niacin, oximetol, oxydemethine M, oxydepropos, parathion A, parathion M, permethrin, pentaerythritol, palmitic acid, Epitope, phorate, phosphatron, phosphat, phosphamidone, pyrazole, pyrimicab, pyrimifos M, pyrimifos A, propenophos, promecab, propafos, propoxur, , Protioate, pimetrozine, pyraclucose, pyridapention, pyrresethrin, pyrretrum, pyridaben, pyrimidifene, pyridopropoxyphene, quinazoline, RH 5992, salitione, But are not limited to, thiophene, opene, sulfotep, sulfopropyl, tebufenozide, Threonine, thionine, thionine, threonine, threonine, threonine, threonine, threonine, threonine, threonine, threonine, threonine, threonine, threonine, threonine, Aratene, triazopos, triazuron, trichlorfon, triflumuron, trimetabic, vimidothion, XMC, xylicarb, YI 5301/5302, zetamethrin.
    Mixtures of other known active compounds, such as herbicides or fertilizers and growth regulators, are also possible.
    The active compounds according to the invention may also be present in the form of their commercially available formulations as a mixture with a synergist and the use forms prepared therefrom. The synergist is a compound that increases the action of the active compound without the added synergist itself needing to be activated.
    The active compound content of the active form prepared from a commercially available preparation can be varied within a considerable range. The concentration of the active compound of the type used is 0.0000001 to 95% by weight, preferably 0.0001 to 1% by weight.
    The compound is used in a conventional manner suitable for the type of use.
    When used in pests of hygiene pests and stored products, the active compounds according to the invention exhibit excellent residual activity against wood and clay and exhibit excellent stability to alkali on the lime surface.
    The active compounds according to the invention are suitable for the treatment of animal parasites (eg parasites), such as ixodid ticks, argacid ticks, scabs (scabs), as well as pests of plants, mites, trombiculid mites, flies (biting and licking), parasitic fly larvae, ducks, hairy ducks, birds and fleas. These parasites include the following:
    Such as Haematopinus spp., Linognathus spp., Pediculus spp., Pthirus spp., Soleil spp. Solenopotes spp.
    For example, Mallophagida neck and Amblycerina and Ischnocerina subsp., Such as Trimenopon spp., Menopon spp., Trinoton spp. ), Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp. Felicola spp.
    Diptera and Nematocerina and Brachycerina subspecies such as Aedes spp., Anopheles spp., Culex spp. (For example, Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp. Crysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Filipomia spp. Such as Staphylococcus spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp. , Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomia spp. Chrysomyia spp.), Such as Wohlfartia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobos spp. Hyppobosca spp., Lipoptana spp., Melophagus spp.
    Siphonaptera sp., Such as Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp., And the like.
    Heteroptera spp., For example, Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
    Blattaridae, for example Blatta orientalis, Periplaneta americana, Blatta germanica, Supella spp., And the like.
    Acarina, Acarida, and Meta- and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otabius spp. , Ixodes spp., Amblyomma spp., Boophilus spp., Dermancentor spp., Haemaphysalis spp., And the like. ), Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Pseudomonas spp. ), Sternostoma spp., And Varroa spp.
    Actinidia (Prostigmata) neck and Acaridida (Astigmata) neck, such as Acarapis spp., Cheyletiella spp. , Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Trombicula spp. ), Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., And the like. ), Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Pseudomonas spp. ), Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp., And the like. ).
    The active compounds of the general formula (I) according to the invention are also suitable for use in agricultural livestock such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, It is suitable for rescuing pets such as dogs, cats, birds in cages and tuna fish, and also arthropods attacking so-called laboratory animals such as hamsters, guinea pigs, rats and mice. The relief of arthropods leads to a reduction in mortality and reduced yields (for example in the production of meat, milk, wool, leather, eggs and honey), so that by using the active compounds according to the invention, Is possible.
    The active compound according to the present invention can be administered orally in the form of tablets, capsules, solutions, powders, granules, pastes or lozenges in the veterinary field by parenteral administration, For example, by intramuscular, subcutaneous, intravenous, intraperitoneal, and the like, by means of injection, by injection (intramuscular, subcutaneous, intravenous and intraperitoneal) And in the form of a molded article containing the active compound, for example in the form of a necklace, an ear tag, a tail tag, a leg band, a sling or a display device, etc., in a manner known percutaneously.
    When administered to animals, poultry, pets, etc., the active compound of the formula (I) is administered directly or as a formulation containing from 1 to 80% by weight of active compound (for example as a powder, emulsion, To 10,000 times dilution, or it can be used as a chemical bath.
    In addition, it has been found that the compounds of formula (I) according to the invention have potent insecticidal activity against insects that destroy industrial materials.
    The following insects are mentioned as preferred examples and are not intended to limit the invention:
    Beetles, for example, Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, For example, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, and the like. But are not limited to, Minthes rugicollis, Xyleborus species, Tryptodendron species, Apate monachus, Bostrychus capucins, Heterobos tricus brunneu (Heterobostrychus brunnes), sinok Ceylon (Synoxylon) species, Dino de Luz minu tooth (Dinoderus minutus)
    Dermapterans, for example, Sirex jubencus, Urocerus gigas, Urocerus gigas taignus, Urocerus gigas, augur)
    Termites such as, for example, Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, , Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coffea, and the like. Coptotermes formosanus (Coptotermes formosanus)
    Bristletails, for example, Lepisma saccharina.
    Industrial materials in this context are understood to mean inanimate materials, such as, for example, synthetic materials, adhesives, sizes, paper and board, leather, wood and wood products, and paints.
    Materials that are particularly desirable to be protected from insect attack are wood and wood products.
    Wood and wood products that can be protected by the compositions according to the invention or mixtures containing such compositions are, for example, building timbers, wood beams, railway sleepers, bridge components, floats, wood vehicles, , Box, pallet, container, telephone pole, wood sign, window or door made of wood, plywood, chip board, connector, or wood product commonly used in house construction or furniture.
    The active compounds can be used, for example, in the form of concentrates or conventional customary preparations such as powders, granules, solutions, suspensions, emulsions or pastes.
    The mentioned preparations can be prepared in a manner known per se, for example by mixing the active compound with one or more solvents or diluents, emulsifiers, dispersants and / or binders or fixing agents, water repellents, if appropriate drying agents and UV stabilizers and, if appropriate, ≪ / RTI > and other processing aids.
    The insecticidal compositions or concentrates used for the protection of wood or wood materials contain the active compounds according to the invention in concentrations of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
    The amount of composition or concentrate used will depend on the frequency and medium of insects and insects. The optimum dose can be determined by a series of tests in each case. However, it is generally sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the substance to be protected.
    The solvent and / or diluent used may be an organic chemical solvent or solvent mixture and / or an oily or oil-type nonvolatile organic chemical solvent or solvent mixture and / or a polar organic chemical solvent mixture or solvent mixture and / Emulsifiers and / or wetting agents.
    Organic chemical solvents which are preferably used are oil-in-water or oil-type solvents having an evaporation number of 35 or more and flash points of 30 DEG C or more, preferably 45 DEG C or more. The materials used as oily or oil-based solvents of this type are non-volatile and water-insoluble oily or oil-like solvents are those which contain suitable mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / Benzene,
    Materials which can be advantageously used are mineral oils with a boiling range from 170 to 220 占 폚, white spirits with a boiling range from 170 to 220 占 폚, spindle oil with a boiling range from 250 to 350 占 폚, boiling ranges from 160 to 280 占Or an aromatic compound, terpentine essence, and the like.
    In a preferred embodiment, liquid aliphatic hydrocarbons having a boiling range of 180 to 210 DEG C or high-boiling mixtures of aromatic and aliphatic hydrocarbons having a boiling range of 180 to 220 DEG C and / or spindle oil and / or monochloronaphthalene, Alpha -monochloronaphthalene is used.
    Organic nonvolatile oily or oil type solvents having an evaporation index of 35 or higher and a flash point of 30 캜 or higher, preferably 45 캜 or higher, are preferred because the solvent mixture also has an evaporation index of 35 or higher and a flash point of at least 30 캜, If the pesticide / fungicide mixture is soluble or parasitic to the mixed solvent, it can be replaced with an organic chemical solvent that is partially highly volatile or has an intermediate volatility.
    In a preferred embodiment, some of the organic chemical solvent or solvent mixture is replaced with a polar aliphatic organic chemical solvent or solvent mixture. The materials preferably used are aliphatic organic and chemical solvents with hydroxyl and / or ester and / or ether groups, such as glycol ethers, esters and the like.
    Organic chemical binders within the scope of the present invention include those which are known per se and which can be diluted with water and / or can be dissolved or dispersed or emulsified in an organic chemical solvent which is used, and / or synthetic resins, in particular acrylate resins, vinyl Resins such as polyvinyl acetate, polyester resins, polycondensation or addition resins, polyurethane resins, alkyd resins or modified alkyd resins, phenol resins, hydrocarbon resins such as indane / coumarone resins , Silicone resins, dry vegetable oils and / or dry oils and / or physical dry binders based on natural and / or synthetic resins.
    The artificial resins used as binders can be used in the form of emulsions, dispersions or solutions. Less than 10% of a bituminous or bituminous material can also be used as the binder. In addition, colorants, pigments, water repellents, aromatic substances and inhibitors or corrosion inhibitors known per se can also be used.
    The compositions or concentrates according to the invention preferably contain at least one alkyd resin or modified alkyd resin and / or dried vegetable oil as the organic chemical binder. Preferably used in accordance with the present invention is an alkyd resin having an oil content of at least 45 wt%, preferably 50 to 68 wt%.
    All or a portion of the binders mentioned above may be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization, crystallization or precipitation of the active compound. They preferably replace 0.01 to 30% (based on 100% of the binder used) of the binder.
    The plasticizers may be selected from the group consisting of phthalic acid esters such as dibutyl phthalate, dioctyl phthalate or benzyl butyl phthalate, phosphoric esters such as tributyl phosphate, adipic esters such as di- (2-ethylhexyl) Adipates, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerol ethers or relatively high molecular weight glycol ethers, glycerol esters and p-toluenesulfonic esters .
    The fixing agent is chemically based on polyvinyl alkyl ethers, such as polyvinyl methyl ether, or a ketone, for example, benzophenone or ethylene benzophenone.
    As solvents and diluents, water is particularly suitable as a mixture with the aforementioned organic chemical solvents or diluents, emulsifiers and dispersants as appropriate.
    Particularly effective protection of the wood is achieved by means of large scale industrial impregnation methods, for example vacuum, double vacuum or pressurized methods.
    If appropriate, the immediate-use composition may additionally contain further pesticides and, if appropriate, one or more further fungicides.
    A further suitable component which can be admixed is preferably an insecticide or fungicide mentioned in WO 94/29 268. The compounds mentioned in the above references are expressly incorporated by reference in this application.
    Very particularly preferred ingredients which can be admixed are insecticides such as chlorpyrifos, zirconia, silafluoropine, alpha methaline, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, And fungicides such as fenoxyluron, hexaflumuron and triflumuron and fungicides such as epoxiconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, ciproconazole, metconazole, imazalil , Dichlorofluanid, tolyl fluoride, 3-iodo-2-propynyl butyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octyl isothiazoline- 3-on.
    The preparation and use of the active compounds according to the invention can be seen from the following examples.
    Manufacturing Example
    Example 1

    (Method a)
    5.0 g (19.6 mmol) of 3- (2-chloropyridin-5-yl-methyl) -2-nitro-methylene- imidazolidine with 3.0 ml of methyl glycinate hydrochloride with 3.6 ml of 37% strength formaldehyde solution (23.9 mmol) and 3.3 ml of triethylamine were dissolved in 30 ml of ethanol and heated under reflux for 5 hours.
    The reaction mixture was cooled and the solvent was evaporated under reduced pressure to concentrate. The residue was stirred with water, filtered off under suction and dried.
    Methyl-6-methoxycarbonyl-methyl-8-nitro (5H) -imidazolidino- [2, 3-f] -pyrimidine. ≪ / RTI >
    Example 2

    (Method b)
    To a solution of 6,7-dihydro-6-ethoxycarbonyl-methyl-8- (5H) -imidazolidino- [2,3- f] -pyrimidine (Example IV-1) in 20 ml acetonitrile 1.5 g (5.86 mmol) was treated with 1.6 g of potassium carbonate and 1.0 g (6.0 mmol) of 2-chloro-5-chloromethylthiazole. The reaction mixture was stirred at 40 < 0 > C for 6 hours. The insoluble material was then filtered and the solution was evaporated to dryness. The residue was purified by column chromatography.
    6-ethoxycarbonyl-methyl-8-nitro- (5H) -imidazolidino- [2-chlorothiazol-5-yl- 2,3-f] -pyrimidine. ≪ / RTI >
    Preparation of starting material

    2.0 g (20.2 mmol) of 2-nitromethylene-imidazolidine in 30 ml of ethanol are mixed with 2.8 g (20.1 mmol) of ethylglycinate hydrochloride, 2.7 ml of triethylamine and 4 ml of a 37% strength aqueous formaldehyde solution Were mixed and heated under reflux for 10 hours. The reaction mixture was cooled and the solvent was distilled and concentrated. The residue was partitioned between water and diethyl ether and the organic phase was separated, dried over sodium sulfate and concentrated.
    2.0 g of 6,7-dihydro-6-ethoxycarbonylmethyl-8-nitro- (5H) -imidazolidino- [2,3-f] -pyrimidine with a melting point of 155-158 deg.
    Following the procedure of Examples 1 and 2 and according to the general manufacturing instructions, the compounds of the general formula (I) listed in Table 1 below were obtained:
    Table 1

    (Table 1 continued)

    (Table 1 continued)

    *) Lg. P = logarithm of the partition coefficient P of the substance between the solvent octanol and water, determined experimentally by reversed-phase HPLC.
    Compounds of general formula I
    A is .

    The starting material of the general formula (IV) listed in the following Table 2 was obtained by the method of Example 2 and according to the general manufacturing instructions:
    Table 2

    Use Example
    In the following examples, the following compounds were used as reference compounds:

    (All compounds are disclosed in EP-A 0 247 477)
    Example A
    Paeon larvae test
    Solvent: Dimethylformamide 7 parts by weight
    Emulsifier: alkylaryl polyglycol ether 1 part by weight
    1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of the emulsifying agent and the concentrate is diluted with water to the desired concentration to prepare a suitable preparation of the active compound.
    Cabbage leaves (Brasica oleracea) were treated by immersion in the active compound preparation at the desired concentration and infected with mustard beetle (Paedoncolearia) larvae while the leaves were wet.
    After a certain period of time,% remission rate was determined. 100% means all beetle larvae have been killed; 0% means that the beetle larvae were not killed at all.
    In this test, for example, the compounds of Preparative Examples 1, 3, 4, 7, 9, 10, 11, 12, 14, 19, 20, 22 and 23, at an exemplary active compound concentration of 0.001% (A), (B), (C) and (E) show no action and show only a remission rate of 30% and only 40% of the compounds And showed a relief rate of only 20%.
    Example B
    Flutella test
    Solvent: Dimethylformamide 7 parts by weight
    Emulsifier: alkylaryl polyglycol ether 1 part by weight
    1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of the emulsifying agent and the concentrate is diluted with water to the desired concentration to prepare a suitable preparation of the active compound.
    Cabbage leaves (Brasica oleracea) were treated by immersion in the active compound preparation at the desired concentration and infected with cabbage moth (Plutella maculipennis) caterpillars while the leaves were wet.
    After a certain period of time,% remission rate was determined. 100% means that all caterpillars have been killed; 0% means that the caterpillar has not been killed at all.
    In this test, for example, the compounds of Preparative Examples 1, 6, 8, 9, 10, 11, 12, 13, 14, 15, 17, 19, 21 and 22, at an exemplary active compound concentration of 0.01% After 3 days in each case, 100% remission was achieved, while the known compound (E) showed no activity.
    Example C
    Spodoptera frugiperda test
    Solvent: Dimethylformamide 7 parts by weight
    Emulsifier: alkylaryl polyglycol ether 1 part by weight
    1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of the emulsifying agent and the concentrate is diluted with water to the desired concentration to prepare a suitable preparation of the active compound.
    The cabbage leaves (Brasica oleracea) were treated by immersion in the active compound preparation at the desired concentration and infected with the oolitmot (Spodoptera frugiperda) caterpillars while the leaves were wet.
    After a certain period of time,% remission rate was determined. 100% means that all caterpillars have been killed; 0% means that the caterpillar has not been killed at all.
    In this test, the compounds of Preparative Examples 8, 9, 10, 11, 12, 14, 15, 19 and 20, at an exemplary active compound concentration of 0.001%, after 3 days in each case, had a 100% (B), (C) and (G) showed only a 30% rescue rate. The compounds (A), (D) and (F)
    Example D
    Nephotettix test
    Solvent: Dimethylformamide 7 parts by weight
    Emulsifier: alkylaryl polyglycol ether 1 part by weight
    1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of the emulsifying agent and the concentrate is diluted with water to the desired concentration to prepare a suitable preparation of the active compound.
    Rice seedlings (Oryzae sativa) were treated by immersion in the active compound preparation at the desired concentration and infested with larvae of green rice leaf hopper (Nephotettix cincticeps) while the seedling was damp.
    After a certain period of time,% remission rate was determined. 100% means that all endmills have been killed; 0% means that the endoptera was not killed at all.
    In this test, the compounds of Preparative Examples 6, 7, 8, 9, 10, 14, 15, 16, 17 and 18, at an exemplary active compound concentration of 0.0001%, after 6 days in each case, , While the known compound (E) showed only a 20% rescue rate.
    Example E
    Myzus Exam
    Solvent: Dimethylformamide 7 parts by weight
    Emulsifier: alkylaryl polyglycol ether 1 part by weight
    1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of the emulsifying agent and the concentrate is diluted with water to the desired concentration to prepare a suitable preparation of the active compound.
    Vicia faba infested with peach louse aphid (Myzus percicae) was treated by immersion in the active compound preparation at the desired concentration and placed in a plastic dish.
    After a certain period of time,% remission rate was determined. 100% means that all peach aphids have been killed; 0% means that the peach aphid did not die at all.
    In this test, the compounds of the following preparation examples were used at an exemplary active compound concentration of 0.001%, 1 = 99%, 4 = 80%, 6 and 16 = 90%, 15 = 98% and 20 = 100%, while the known compounds (E) and (F) showed only 10% and no action at all.
    权利要求:
    Claims (9)
    [1" claim-type="Currently amended] The tetrahydropyrimidine derivative of general formula (I)

    In this formula,
    A is the group (Ia) - (CH 2) m-COXR 1 and (Ib) , ≪ / RTI >
    Het is a heteroatomic ring containing 1, 2, 3 or 4 nitrogen atoms and / or one or two oxygen or sulfur atoms and the number of ring heteroatoms is 1, 2, 3 or 4 and is halogen, cyano , Nitro, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, alkynyl, alkoxy, halogenoalkoxy, alkenyloxy, halogenoalkenyloxy, alkynyloxy, alkylthio, halogenoalkylthio, alkenyl Alkylthio, arylthio, arylthio, haloalkylthio, arylthio, arylthio, arylthio, arylthio, arylthio, arylthio, arylthio, arylthio, arylthio Or a 5-or 6-membered heterocyclic group optionally substituted by one or more substituents selected from the group consisting of amino, aralkyl, formylamino, alkylcarbonylamino, formyl, carbamoyl, alkylcarbonyl and alkoxycarbonyl,
    R 1 represents hydrogen, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, optionally substituted aralkyl or optionally substituted 5- or 6-membered heterocyclylalkyl,
    R < 2 > represents optionally substituted alkyl or aralkyl,
    X represents oxygen or a group -NH- or -N-alkyl-,
    m represents an integer of 1 to 20,
    n represents an integer of 0 to 2,
    However,
    A represents a group (Ia)
    Het has Lt; / RTI >
    R 1 represents hydrogen or ethyl,
    X represents oxygen,
    m represents 1 or 2,
    Compounds in which n represents 0 are excluded.
    [2" claim-type="Currently amended] a) dissolving a nitromethylene derivative of the formula (II) in the presence of at least twice the molar amount of formaldehyde, if appropriate in the presence of an acid catalyst and, if appropriate, in the presence of a diluent and if appropriate in the presence of a base, With an amine of formula (IIIa) or (IIIb)
    b) reacting the nitropyrimidine derivative of general formula (IV) with a compound of general formula (V) in the presence of a base and if appropriate in the presence of a diluent, with a compound of general formula (I) Preparation of tetrahydropyrimidine derivatives:


    H 2 N- (CH 2 ) m -CO-X R 1 (IIIa)


    Het-CH 2 -L (V)
    In this formula,
    A is the group (Ia) - (CH 2) m-COXR 1 and (Ib) , ≪ / RTI >
    Het is a heteroatomic ring containing 1, 2, 3 or 4 nitrogen atoms and / or one or two oxygen or sulfur atoms and the number of ring heteroatoms is 1, 2, 3 or 4 and is halogen, cyano , Nitro, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, alkynyl, alkoxy, halogenoalkoxy, alkenyloxy, halogenoalkenyloxy, alkynyloxy, alkylthio, halogenoalkylthio, alkenyl Alkylthio, arylthio, arylthio, haloalkylthio, arylthio, arylthio, arylthio, arylthio, arylthio, arylthio, arylthio, arylthio, arylthio Or a 5-or 6-membered heterocyclic group optionally substituted by one or more substituents selected from the group consisting of amino, aralkyl, formylamino, alkylcarbonylamino, formyl, carbamoyl, alkylcarbonyl and alkoxycarbonyl,
    R 1 represents hydrogen, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, optionally substituted aralkyl or optionally substituted 5- or 6-membered heterocyclylalkyl,
    R < 2 > represents optionally substituted alkyl or aralkyl,
    X represents oxygen, or group -NH- or -N-alkyl-,
    m represents an integer of 1 to 20,
    n represents an integer of 0 to 2,
    However,
    A represents a group (Ia)
    Het has Lt; / RTI >
    R 1 represents hydrogen or ethyl,
    X represents oxygen,
    m represents 1 or 2,
    Compounds in which n represents 0 are excluded,
    L is an anionic leaving group.
    [3" claim-type="Currently amended] The nitropyrimidine derivative of general formula (IV):

    In this formula,
    A is the group (Ia) - (CH 2) m-COXR 1 and (Ib) , ≪ / RTI >
    R 1 represents hydrogen, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, optionally substituted aralkyl or optionally substituted 5- or 6-membered heterocyclylalkyl,
    R < 2 > represents optionally substituted alkyl or aralkyl,
    X represents oxygen or a group -NH- or -N-alkyl-,
    m represents an integer of 1 to 20,
    n represents an integer of 0 to 2;
    [4" claim-type="Currently amended] The nitromethylene derivatives of the general formula (IIa) are reacted in the presence of at least twice the molar amount of formaldehyde, if appropriate in the presence of an acid catalyst and if appropriate in the presence of a diluent and if appropriate in the presence of a base, (IV) according to claim 3, characterized in that it is reacted with an amine of formula (IIIa) or (IIIb): < EMI ID =

    H 2 N- (CH 2 ) m -CO-X R 1 (IIIa)

    In this formula,
    n represents an integer of 0 to 2,
    R 1 , R 2 , X and m are as defined in claim 3.
    [5" claim-type="Currently amended] A pesticide characterized in that it comprises at least one tetrahydropyrimidine of the general formula (I) according to claim 1.
    [6" claim-type="Currently amended] Use of a tetrahydropyrimidine of general formula (I) according to claim 1 for pest control.
    [7" claim-type="Currently amended] Characterized in that the tetrahydropyrimidines of general formula (I) according to claim 1 are acting on pests and / or their habitats.
    [8" claim-type="Currently amended] Characterized in that the tetrahydropyrimidine of the general formula (I) according to claim 1 is mixed with an extender and / or a surfactant.
    [9" claim-type="Currently amended] Use of a tetrahydropyrimidine of general formula (I) according to claim 1 for the preparation of pesticides.
    类似技术:
    公开号 | 公开日 | 专利标题
    EP0773920B1|2000-01-26|2-|cyclopentane-1,3-dione derivatives
    US7122506B2|2006-10-17|Cyclic imines as pesticides
    ES2248846T3|2006-03-16|Cyclic cetoenols substituted by phenyl.
    US6133296A|2000-10-17|Substituted pyridyl keto enols
    JP3847335B2|2006-11-22|2-Arylcyclopentane-1,3-dione derivatives
    ES2296316T3|2008-04-16|Substituted phenylcetolenols and its use as pesticides.
    JP4422891B2|2010-02-24|Use of spirocyclic phenylketo-enols as pesticides and herbicides
    EP0915846B1|2003-04-23|2- and 2,5-substituted phenylketoenols
    US6251833B1|2001-06-26|2-arylcyclopentan-1,3-diones
    JP4404478B2|2010-01-27|Novel substituted phenylketoenol
    KR100556636B1|2006-05-25|Synergistic insecticide mixtures
    US5977029A|1999-11-02|3-aryl-5-halogen-pyrone derivatives as pest control agents
    US6569810B1|2003-05-27|Cyclopentane-1,3-dione derivatives
    US6051723A|2000-04-18|3-aryl-tetronic acid derivatives
    US20070112035A1|2007-05-17|Substituted oxyarenes
    EP1383751B1|2007-01-17|Novel azoles having an insecticidal action
    JP4434317B2|2010-03-17|3-thiocarbamoylpyrazole derivatives as pest control agents
    DE10024934A1|2001-11-22|Pesticidal agent contains synergistic mixture of 3-aryl-4-hydroxy-2-oxo-pyrroline derivative and nicotinergic acetylcholine receptor agonist or antagonist
    US6576771B1|2003-06-10|Oxymethoxy-3-aryl-pyrone derivatives
    EP0296453B1|1997-08-13|Nitrosubstituted heterocyclic compounds
    KR20070033980A|2007-03-27|Azinil imidazoazine and azinyl carboxamide
    EP1359803B1|2007-12-19|Synergistic pesticide mixtures for the control of animal pests
    CA2225756C|2008-09-09|Substituted cyanophenyl uracils
    EP1077938B1|2005-04-13|2-|-3,4-dihydro-2h-pyrrol derivatives
    ES2215199T3|2004-10-01|5-aminoisotiazoles acilated with insecticide effect, intermediate products and procedures for obtaining it.
    同族专利:
    公开号 | 公开日
    DE19651429A1|1997-09-11|
    KR100492505B1|2006-03-28|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    法律状态:
    1996-03-04|Priority to DE19608243
    1996-03-04|Priority to DE19608243.9
    1996-12-11|Priority to DE19651429.0
    1996-12-11|Priority to DE1996151429
    1997-02-19|Application filed by 빌프리더 하이더, 바이엘 악티엔게젤샤프트
    1999-12-15|Publication of KR19990087152A
    2006-03-28|Application granted
    2006-03-28|Publication of KR100492505B1
    优先权:
    申请号 | 申请日 | 专利标题
    DE19608243|1996-03-04|
    DE19608243.9|1996-03-04|
    DE19651429.0|1996-12-11|
    DE1996151429|DE19651429A1|1996-03-04|1996-12-11|Tetrahydropyrimidine derivatives|
    [返回顶部]