KR100492505B1 - Tetrahydropyrimidine derivatives - Google Patents

Abstract

The present invention relates to novel tetrahydropyrimidine derivatives of general formula (I), methods for their preparation and their use as pesticides:

Where

A is a group (Ia)-(CH ₂ ) m-COXR ¹ and (Ib) Represents one of

Het is a hetero atom reduction containing 1, 2, 3 or 4 nitrogen atoms and / or one or two oxygen or sulfur atoms, the number of ring hetero atoms being 1, 2, 3 or 4, halogen, cyano , Nitro, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, alkynyl, alkoxy, halogenoalkoxy, alkenyloxy, halogenoalkenyloxy, alkynyloxy, alkylthio, halogenoalkylthio, alkenyl Thio, halogenoalkenylthio, alkynylthio, alkylsulfinyl, halogenoalkylsulfinyl, alkylsulfonyl, halogenoalkylsulfonyl, amino, alkylamino, dialkylamino, aryl, aryloxy, arylthio, aryl A 5- or 6-membered heterocyclic group optionally substituted by amino, aralkyl, formylamino, alkylcarbonylamino, formyl, carbamoyl, alkylcarbonyl and / or 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 from 1 to 20,

n represents an integer of 0 to 2,

However, at the same time

A represents group (Ia),

Het Indicates

R ¹ represents hydrogen or ethyl,

X represents oxygen,

m represents 1 or 2,

Compounds in which n represents 0 are excluded.

Description

Tetrahydropyrimidine derivatives

The present invention relates to novel tetrahydropyrimidine derivatives, their preparation and their use for controlling animal pests thereof.

Especially 6-substituted 6,7-dihydro-8-nitro- (5H) -1- (2-chloropyridin-5-yl-methyl or 2-chloro-1,3-thiazol-5-yl-methyl Certain bicyclic pyrimidine derivatives, such as) -imidazolidino- [2,3-f] -pyrimidine, are already known to have pesticidal properties (see eg EP-A-0 247 477). . However, the activity and spectrum of action of these compounds are not always completely satisfactory, especially at low application rates and concentrations.

The present invention provides novel tetrahydropyrimidine derivatives of general formula (I):

Where

A is a group (Ia)-(CH ₂ ) m-COXR ¹ and (Ib) Represents one of

Het is a hetero atom reduction containing 1, 2, 3 or 4 nitrogen atoms and / or one or two oxygen or sulfur atoms, the number of ring hetero atoms being 1, 2, 3 or 4, halogen, cyano , Nitro, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, alkynyl, alkoxy, halogenoalkoxy, alkenyloxy, halogenoalkenyloxy, alkynyloxy, alkylthio, halogenoalkylthio, alkenyl Thio, halogenoalkenylthio, alkynylthio, alkylsulfinyl, halogenoalkylsulfinyl, alkylsulfonyl, halogenoalkylsulfonyl, amino, alkylamino, dialkylamino, aryl, aryloxy, arylthio, aryl A 5- or 6-membered heterocyclic group optionally substituted by amino, aralkyl, formylamino, alkylcarbonylamino, formyl, carbamoyl, alkylcarbonyl and / or 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 from 1 to 20,

n represents an integer of 0 to 2,

However, at the same time

A represents group (Ia),

Het Indicates

R ¹ represents hydrogen or ethyl,

X represents oxygen,

m represents 1 or 2,

The compound of general formula (I) in which n represents 0 is excluded.

In addition, tetrahydropyrimidine derivatives of general formula (I)

a) The nitromethylene derivative of formula (II) is optionally in the form of a hydrohalide, optionally 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 React with an amine of formula (IIIa) or (IIIb), or

b) it was found that the nitropyrimidine derivatives of general formula (IV) are obtained by reaction with a compound of general formula (V) in the presence of a base and, where appropriate, in the presence of a diluent:

H ₂ N- (CH ₂ ) _m -CO-XR ¹ (IIIa)

Het-CH ₂ -L (V)

Where

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 general formula (I) have excellent biological properties and control insects, spiders and nematodes encountered in animal pests, particularly agriculture, forestry, protection of stored products and materials, and veterinary medicine. Has been found to be particularly suitable.

Formula (I) provides a general definition of tetrahydropyrimidine derivatives according to the present invention.

Preferred substituents or ranges of the radicals listed in the general formulas mentioned above and below are illustrated:

Het is preferably 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 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 -alkenyl Oxy (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 -alkenylthio (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 Furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3- or 1,2,4-triazolyl, optionally mono- or polysubstituted by the same or different substituents selected from the group consisting of Oxazolyl, isoxazolyl, 1,2,4- or 1,3,4-oxadiazolyl, thiazolyl, isothiazolyl, 1,2,3-, 1,2,4-, 1,2,5 Or 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 1 To phenyl-C ₁ -C ₄ -alkyl optionally substituted by 5 identical or different substituents, suitable phenyl substituents being 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 -alkylamino or di- (C ₁ -C ₄ -alkyl) -amino;

5- or 6-membered heterocycle-C ₁ -C ₄ -alkyl optionally substituted by one to three identical or different substituents, wherein the heterocyclic groups are 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 -alkenylthio, 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 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 The same or 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 Furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3- or 1,2,4-triazolyl, oxazolyl, isoxazolyl, optionally substituted one to three 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 It is selected from the group consisting of diazolyl, pyridyl, pyridazinyl, pyrimidinyl and pyrazinyl.

R ² preferably denotes C ₁ -C ₈ -alkyl or optionally substituted benzyl.

X preferably represents oxygen or a group -NH- or -N- (C ₁ -C ₈ -alkyl)-.

m preferably represents an integer of 1 to 12.

n preferably represents a number of zero or one.

At the same time

A represents group (Ia),

Het Indicates

R ¹ represents hydrogen or ethyl,

X represents oxygen,

m represents 1 or 2,

The compound of general formula (I) in which n represents 0 is excluded.

Het is particularly preferably 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 Pyrazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, optionally mono- to trisubstituted by the same or different substituents selected from the group consisting of: , 5-, 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 three to three identical or different substituents, suitable phenyl substituents being fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, methylthio, Trifluoromethyl, trifluoromethoxy and trifluoromethylthio; 5- or 6-membered heterocycle-C ₁ -C ₂ -alkyl optionally substituted by one to three identical or different substituents, each heterocyclic group being fluorine, chlorine, bromine, 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), or pyrazolyl, 1,2,4- optionally substituted by C ₁ -C ₂ -alkylsulfonyl, which is optionally substituted by fluorine and / or chlorine Triazolyl, oxazolyl, 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 - halogenoalkyl alkoxy, C ₁ -C ₂ - halogenoalkyl alkylthio, it refers to a benzyl optionally substituted with nitro or cyano.

X particularly preferably represents oxygen or a group -NH-, -N (CH ₃ )-or -N (C ₂ H ₅ )-.

m especially preferably represents the integer of 1-10.

n particularly preferably represents a number of zero or one.

At the same time

A represents group Ia,

Het Indicates

R ¹ represents hydrogen or ethyl,

X represents oxygen,

m represents 1 or 2,

Compounds in which n represents 0 are excluded.

Het very particularly preferably represents pyridyl or thiazolyl optionally substituted by one or two identical or different substituents selected from the group consisting of fluorine, chlorine and bromine, respectively.

R ¹ very particularly preferably represents 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; Pyridylmethyl or thiazolylmethyl optionally substituted by one or two identical or different substituents each 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 very particularly preferably represents an integer from 1 to 8.

n very particularly preferably represents a number of zero or one.

At the same time

A represents group Ia,

Het Indicates

R ¹ represents hydrogen or ethyl,

X represents oxygen,

m represents 1 or 2,

Compounds in which n represents 0 are excluded.

The above mentioned general or preferred definitions or examples of radicals apply to the final product and therefore to the starting materials and intermediates correspondingly. These radical definitions can be combined with one another as desired, ie combinations between the respective preferred ranges are also possible.

Preferred according to the invention are compounds of formula (I) which contain as a preferred combination of the definitions given above.

Especially preferred according to the invention are compounds of general formula (I) which contain a combination of the definitions given above as being particularly preferred.

Very particular preference according to the invention is very particular preference to compounds of formula (I) which contain a combination of the definitions given above.

In the radical definitions given above and below, hydrocarbon radicals such as alkyl or alkenyl are also as straight or branched as possible in each case with respect to heteroatoms such as alkoxy or alkylthio.

Preferred compounds according to the invention are substances of the general formulas (Ic) to (If):

Where

Het ¹ represents optionally substituted pyridyl,

Het ² represents optionally substituted thiazolyl,

A is as defined in the definition of the present invention.

Preferred compounds according to the invention are also substance groups of the general formulas (Ia-1), (Ib-1), (Ic-1) and (Id-1):

Where

A is generally preferred, particularly preferred and very particularly preferred as defined above.

For example, 3- (2-chloropyridin-5-yl-methyl) -2-nitromethylene-imidazolidine, methyl glycinate hydrochloride and 2 moles of formaldehyde according to the invention (a) If used to perform the reaction scheme can be illustrated by the following scheme:

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

Nitromethylene derivatives of the general formula (II) used as starting materials in process (a) 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 (see the published European application referred to).

If nitromethylene derivatives are used in the form of hydrohalides, their hydrochlorides are preferred.

The amines of formulas (III-a) and (III-b), which are also used as starting materials in 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 general formula (IV) used as starting materials in the process (b) according to the invention are disclosed. These are obtained by reacting a nitromethylene derivative of formula (IIa) (see eg EP-A 0 247 477) with an amine of formula (III-a) or (III-b) using method (a). can do:

Where

n is as defined above.

Compounds additionally used as starting materials in the 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 substances in organic chemistry.

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. They are preferably aliphatic and aromatic compounds, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, 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 Isopropanol. Preferably a mixture of alcohol and water is used.

Process (a) according to the process is carried out in the presence of an acidic non-oxidation catalyst, if appropriate. Particularly useful are hydrogen halides such as hydrochloric acid and hydrobromic acid, phosphoric acid and lower carboxylic acids such as acetic acid and propionic acid.

The reaction temperature of process (a) according to the invention can vary over a relatively wide range. In general, the process is carried out at temperatures of -20 ° C and + 120 ° C, preferably 0 ° C to + 80 ° C.

Process (a) according to the invention is generally carried out at atmospheric pressure. However, it is also possible to carry out under elevated or reduced pressure.

When carrying out process (a) according to the invention, 1 to 1.5 moles, preferably 1 to 1.2 moles of amine of formula (III) and 2 to 4 moles, preferably 2 to 3 moles of formaldehyde It is used per mol of nitromethylene derivatives of general formula (II).

The amines of general formula (III) can be used as aqueous solutions if appropriate. If gaseous amines of the general formula (III) are used, these compounds can be passed through a mixture of diluents, compounds of the general formula (II) and formaldehyde. In the process according to the invention, formaldehyde is used in aqueous solution. The reaction is generally carried out in a suitable diluent and the reaction mixture is stirred for several hours at the required temperature in each case. The post-treatment in the process according to the invention is carried out in the usual way in each case.

Process (b) according to the invention is preferably carried out using a diluent. Suitable diluents are virtually all inert organic solvents. They are especially aliphatic and aromatic compounds, optionally halogenated hydrocarbons, for example pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene 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, ester, for example methyl acetate or ethyl acetate, nitrile, for example acetonitrile or propionitrile, amide, for example dimethylformamide, dimethylacetamide and N-methylpyrrolidone, and Dimethylsulfoxide, tetramethylene sulfone or hexa Butyl phosphine is porik tree amide.

Suitable bases in processes (a) and (b) according to the invention are all acid binders conventionally employed 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 hydroxide or alkaline earth metal hydroxides, for example lithium hydroxide Sodium hydroxide, potassium hydroxide or calcium hydroxide, alkali metal carbonate or hydrogen carbonate or alkali metal carbonate or hydrogen carbonate, for example sodium carbonate or hydrogen carbonate or potassium carbonate or hydrogen carbonate or calcium Carbonates, alkali metal acetates, for example sodium acetate or potassium acetate, alkali metal alkoxides, for example sodium tert-butoxide or potassium tert-butoxide Ids, 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-dimethyl-, 2-ethyl-, 4 -Ethyl- and 5-ethyl-2-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).

In the process (b) according to the invention the reaction temperature can vary over a relatively wide range. In general, the reaction is carried out at a temperature of 0 ° C to 100 ° C, preferably 10 ° C to 80 ° C.

Process (b) according to the invention is generally carried out at atmospheric pressure. However, it is also possible to carry out under elevated and reduced pressure.

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 a relatively excessive amount 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 required temperature in each case. Post-treatment is carried out in a conventional manner.

The active compounds of animal pests, in particular an agricultural, forestry, the storage product, and insects, spiders animals (Arachnids) and suitable for use in relief of the nematode, and low toxicity to the preferred plant tolerance and a warm-blooded animal that is encountered in the protective and hygienic areas of the material Have These can preferably be used as crop protection agents. The active compound is active against all or some stages of moderately sensitive or resistant species and metamorphosis. The pests mentioned above include:

Isopoda neck, for example Oniscus asellus , Armadillidium vulgare and Porcellio scaber .

Millipedes (Diplopoda) tree, for example Blast niul loose obtain Tula tooth (Blaniulus guttulatus).

The genus Chilopoda , for example Geophilus carpophagus and Scutigera spec .

From the order of Symphyla , for example Scutigerella immaculata .

Thysanura , for example Lepisma saccharina .

Collembola neck, for example Onychiurus armatus .

Orthoptera , for example Blatta orientalis , Periplaneta americana , Leucophaea maderae , Blattella germanica , Ah keta also scalpel Tea Syracuse (Acheta domesticus), talpa species grill (Gryllotalpa spp.), Roku star US Gras Trattoria US Gras Tori cucumber death (Locusta migratoria migratorioides), melanocyte platforms Ruth Depeche Lenti Alice (Melanoplus differentialis) and the rest Stowe Sergio Cagregaria ( Schistocerca gregaria ).

Dermaptera , for example Forficula auricularia .

Termite Isoptera , for example Reticulitermes spp .

Anoplura , for example Pediculus humanus corporis , Haematopinus spp . And Linognathus spp .

Mallophaga , for example Trichodectes spp . And Damalinea spp .

Thysanoptera order, for example Hercinothrips femoralis and Thrips tabaci .

From the order of Heteroptera , for example Eurygaster spp ., Dysdercus intermedius , Piesma quadrata , Cimex lectularius , Rodney Rhodnius prolixus and Triatoma spp .

Cicadas (Homoptera) neck, for the example Alessio right des Brassica (Aleurodes brassicae), bemi cyano other Bridge (Bemisia tabaci), the tree Valley right des bar Fora Rio room (Trialeurodes vaporariorum), Apis notice blood (Aphis gossypii), the breather Vico Rhine Brassica (Brevicoryne brassicae), the creep Tommy juice Leavis (Cryptomyzus ribis), Apis wave bar (Aphis fabae), Apis breech (Aphis pomi), Erie O Soma Raney gerum (Eriosoma lanigerum), hyaluronic rope Teruel's Arun Dinis ( Hyalopterus arundinis ), Phylloxera vastatrix , Pemphigus spp ., Macrosiphum avenae , Myzus spp ., Phorodon Humulley humuli , Rhopalosiphum padi , Empoasca spp ., Eucelis bilobatus, Nephotettix cincticeps , Lecanium corni ), The poinsettia Ole Ah between (Saissetia oleae), Lao del Parks Austria Tel Ruth (Laodelphax striatellus), Neela Parque Bata Lou Regensburg (Nilaparvata lugens), Oh sludge de Ella Augusta is T (Aonidiella aurantii), Oh Speedy ohtuseu Aspidiotus hederae , Pseudococcus spp . And Psylla spp .

Lepidoptera neck, for example Pectinophora gossypiella , Bupalus piniarius , Cheimatobia brumata , Lithocolletis blancardella , Hyponomeuta padella , Plutella maculipennis , Malacosoma neustria , Euproctis chrysorrhoea , Lymantria spp . ), part Kula matrix Tour Barry Ella (Bucculatrix thurberiella), Philo greatest seutiseu sheet mozzarella (Phyllocnistis citrella), Agrobacterium-Tees species (Agrotis spp.), six pediatric species (Euxoa spp.), Pell Tia species (Feltia spp.), Arias on the Peninsula or (Earias insulana), Heliothis species (Heliothis spp.), Spodoptera guar (Spodoptera exigua), Mame Strahan on brassica (Mamestra brassicae), propanol leasing platform ramme (Panolis flammea), Spodoptera Li Natura (Spodoptera litura), Spodoptera species (Spodoptera spp.), Tricot flu cyano Needle (Trichoplusia ni), car reportage CAP sanding Monella.All (Carpocapsa pomonella), the blood EPO species (Pieris spp .), Chilo spp ., Pyrausta nubilalis , Ephestia kuehniella , Galleria mellonella , Tineola bisselliella , Tinea pellionella , Hofmannophila pseudospretella , Cacoecia podana , Capua reticulana , Coristoneura pumiferana Choristoneura fumiferana ), Clysia ambiguella , Homona magnanima and Tortrix viridana .

Coleoptera (e.g., Anobium punctatum ), Rhizopertha dominica , Bruchidius obtectus , Acanthoscelides obtectus , Hylotrupes bajulus , Agelastica alni , Leptinotarsa decemlineata , Phaedon cochleariae , Diabrotica spp. .), Psylliodes chrysocephala , Epilachna varivestis , Atomaria spp ., Oryzaephilus surinamensis , Antoninomus species (Anthonomus spp.), Citrus peel loose species (Sitophilus spp.), cut out ot kusu sulka tooth (Otiorrhynchus sulcatus), poly Cosmo test sorbitan di Douce (Cosmopolites sordidus), establish Torin Scotland know Millie's (Ceuthorrhynchus assimilis), Hebrews Blow Force Galactica (Hypera postica), no scalpel test species (Dermestes spp.), Tree logo Dumaguete species (Trogoderma spp.), No trail pandanus species (Anthrenus spp.), Oh ride Attagenus spp ., Lyctus spp ., Meligethes aeneus , Ptinus spp ., Niptus hololeucus , Gibiumuf Gibbium psylloides , Tribolium spp ., Tenebrio molitor , Agriotes spp ., Conoderus spp ., Melonta Melonta ( Melolontha melolontha ), Amphimallon solstitialis and Costelytra zealandica .

Hymenopera species, for example Diprion spp ., Hoplocampa spp ., Lasius spp ., Monomorium pharaonis and Vespa species Vespa spp .).

Diptera , for example Aedes spp ., Anopheles spp ., Culex spp ., Drosophila melanogaster , Musca species. 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 ., Pegomia hisosiami ( Pegomyia hyoscyami ), Ceratitis capitata , Dacus oleae and Tipula paludosa ( Tipula paludosa ).

From the order of Siphonaptera , for example Xenopsylla cheopis and Ceratophyllus spp .

Arachnida , for example Scorpio maurus , Latrodectus mactans .

Mite ( Acarina ), for example Acarus siro , Argas spp ., Ornithodoros spp ., Dermanyssus gallinae , Eriopis libis ( 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 plastic ethylene kusu species (Pratylenchus spp.), Any pole loose during mm's (Radopholus similis), di-ethylene kusu deep deviation (Ditylenchus dipsasi), butyl renkul loose semi-phenethyl trans (Tylenchulus semipenetrans), heteroaryl Temple species ( Heterodera spp .), Globodera spp ., Meloidogyne spp ., Apelenchoides spp ., Longidorus spp ., Xypinene species ( Xiphinema spp .) And Trichodorus spp .

The active compounds of formula (I) of the present invention have particularly excellent pesticide activity.

They are especially plant-damaging insects, such as mustard beetles ( Phaedon cochlaeriae ), caterpillars of Plutella maculipennis , green rice cicada ( Nephotettix cinctriceps ) and oult moths . ( owlet moth ) ( Spodoptera frugiperda ), or peach leaf aphids ( Myzus percicae ) can be successfully used to control.

Active compounds include solutions, emulsions, hydrating powders, suspensions, powders, powders, pastes, soluble powders, granules, suspension emulsion concentrates, natural and synthetic substances impregnated with the active compounds, and microcapsules in polymeric materials. It may be converted to a conventional formulation.

These formulations are prepared by known methods, for example by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, optionally using surfactants, ie emulsifiers and / or dispersants and / or foam-forming agents. .

When water is used as the extender, for example an organic solvent can also be used as an auxiliary solvent. Liquid solvents are mainly aromatic compounds such as xylene, toluene or alkylnaphthalene, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride, cyclohexane or paraffins, for example mineral oil fractions, mineral oils and vegetable oils. Alcohols such as aliphatic hydrocarbons, butanol or glycol and ethers and esters thereof, as well as strong polar solvents such as ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, dimethylformamide and dimethyl sulfoxide, are suitable 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 dispersed silica, alumina and silicates. This is suitable. Solid carriers for granulation include, for example, pulverized and classified natural rocks such as calcite, marble, pumice, calcite and dolomite, and synthetic granules of inorganic and organic powders, and organic such as sawdust, coconut husk, corncobs and tobacco stems. Granules of material are suitable. Emulsifiers and / or foam-forming agents include, for example, nonionic and anionic emulsifiers, for example polyoxyethylene fatty alcohol ethers such as polyoxyethylene fatty acid esters, alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, aryls Sulfonates and proteolytic products are suitable. Suitable dispersants are, for example, lignin-sulfite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose, gum arabic, polyvinyl alcohol and polyvinyl acetate, powders, natural and synthetic polymers in granular or latex form, and natural phospholipids such as cephalin and lecithin, and synthetic phospholipids may be used in the formulation. Can be. As other additives, mineral oil and vegetable oil may be used.

Inorganic pigments such as iron oxide, titanium oxide and prussian blue, and colorants such as alizarin dyes, azo dyes and organic dyes such as metal phthalocyanine dyes and micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc You can also use

The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight of active compound.

The active compounds according to the invention are preparations commercially available as a mixture with other active compounds such as insecticides, attractants, sterilizers, bactericides, acaricides, nematicides, fungicides, growth-modulating substances or herbicides and these It may be present in the form of use prepared from the formulation. Pesticides include, for example, phosphates, carbamates, carboxylates, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and the like.

Examples of particularly advantageous components for the mixture are as follows:

         Fungicides:

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-1,3-thiazole-5-carboxanilide; 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; 2-phenylphenol (OPP), Aldimorph, Ampropyl Force, Aniazine, Azaconazole, Benalacyl, Benodanil, Benomil, Binapacryl, Biphenyl, Vitertanol, Blastisidin-S, Bromuconazole, burimate, butiobate, calcium polysulfide, captapol, captan, carbendazim, carboxycin, quinomethionate, chloroneb, chloropicrine, chlorothalonil, clozolinate, cupraneb, Cymoxanyl, cyproconazole, cyprofuram, dichlorophene, diclobutrazole, diclofloanide, diclomezin, dichloran, dietofencarb, difenokazole, dimethymolol, dimethomorph , Diconazole, dinocap, diphenylamine, dipyrithione, ditalimfoss, dithianon, dodine, drazoxolone, edifene force, epoxyconazole, etirimole, ethriazole, phenarimol, fenbuco Nazol, fenfuram, phenytropane, fenpiclonyl, fenpropidine, fenpropormoff, fentin ah Tate, fentin hydroxide, ferbam, perimzone, fluazinam, fludioxonil, fluoromid, fluquinconazole, flusilazole, flusulfamid, flutoranyl, flutriafol, polpet, pocetyl- Aluminum, phthalide, fuberidazole, furalacsil, purmecyclox, guazin, hexachlorobenzene, hexaconazole, hymexazole, imazaryl, imibenconazole, iminooctadine, ifprobenfos (IBP) , Isprodione, isoprothiolane, kasugamycin, copper preparations such as copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, auxin-copper and Bordeaux mixtures, mancopers, mancozebs , Maneb, mepanipyrim, mepronyl, metallaxyl, metconazole, metasulfocarb, metfuroxam, metiram, metsulfobox, michaelrobutanyl, nickel dimethyldithiocarbamate, nitrotal Isopropyl, Noari Mall, Opuras, Oxadik Yarn, oxamocarb, oxycarboxycin, pepurazoate, fenconazole, penicuron, phosphodiphene, phthalide, fimaricin, piperaline, polycarbamate, polyoxin, probenazole, prochloraz, pro Simidone, propamocarb, propiconazole, propineb, pyrazophos, pyriphenox, pyrimethanyl, pyroquilon, quintogen (PCNB), sulfur and sulfur preparations, tebuconazole, teclophthalam, Tecnazen, tetraconazole, thibendazole, thiathiophene, thiophanate-methyl, thiram, tollclofos-methyl, tolylufluoride, triadimefon, triadimenol, triazoxide, trichlamide, Tricyclazole, tridemorph, triflumizol, tripolin, triticazole, validamycin A, vinclozoline, geneb, zelam.

        Salbacterase:

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octylinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, teclophthalam, copper sulfate and other copper agents.

        Pesticides / Acaricides / Nematicides:

Abamectin, AC 303 630, Acetate, Acrinatrin, Alanicab, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Ajinfoss A, Ajinfoss M, Azo Cyclotin, Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Beta-Cyflulutin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Bupropezin, Butocacarsim , Butylpyridaben, kadusafos, carbaryl, carbofuran, carbophenocion, carbosulphan, cartop, CGA 157419, CGA 184699, chloretocarb, chlorethoxyphosphate, chlorfenbinfos, chlorfluazuron, chlorme Force, Chlorpyriphos, Chlorpyriphos M, Cis-Resmethrin, Closightin, Clofentezin, Cyanophosph, Cycloprotrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cylo Margin, Deltamethrin, Demetone-M, Demetone-S, Demetone-S-methyl, Dia Pentiuron, diazinon, diclopention, dichlorboth, diclifoss, dicrotophos, diethione, diflubenzuron, dimethatoate, dimethylbinfoss, dioxation, disulfotone, ediffenfoss, emma Mectin, Espenvalate, Ethiophenecarb, Ethion, Etofenprox, Etoprophos, Etrifoam, Phenamifoss, Penazaquine, Penbutatin, Phenytrothion, Phenobucarb, Phenothiocarb , Phenoxycarb, phenpropartin, fenpyrad, fenpyroximate, pention, fenvalrate, fipronil, fluazinam, flucycloxanthone, flucitalinate, flufenoxuron, flufenprox , Fluvalinate, phonophos, formitol, phosphthiazate, fufenfenx, furathiocarb, HCH, heptenophos, hexaflumuron, hexiax, imidacloprid, isprobenfos, isazofoss , Isopenfoss, isoprocarb, isoxation, ibemec Tin, lambda-cyhalothrin, lufenuron, malathion, mecarbam, mebinfos, mesulfenfos, metaldehyde, metacryphos, metamidophos, methidathione, methiocarb, methamyl, methol Carb, Milvemectin, Monoclotophos, Moxidecin, Naled, NC 184, NI 25, Nitenpyram, Ometoate, Oxamyl, Oxidemetone M, Oxidepropos, Parathion A, Parathion M, Permethrin, Pento Eight, Forate, Posalone, Posmet, Phosphomidone, Bombide, Pyrimicarb, Pyrimiphos M, Pyrimiphos A, Propenophos, Promecarb, Propaphos, Propoxur, Prothiophos , Protoate, pymetrozine, pyraclophos, pyridapention, pyresmethrin, pyrethrum, pyridaben, pyrimidipene, pyripropoxyphene, quinalforce, RH 5992, salityon, cebufoss, silaflu Offen, sulfopep, sulfprofos, tebufenozide, tebufenpyrad, tebupyrimifos, Flubenzuron, tefluthrin, temefos, terbam, terbufos, tetrachlorbinfos, thiaphenox, thiodicarb, thiophanox, thiometone, thionazine, turingiencin, tralomethrin, tri Aratene, triazofoss, triazuron, trichlorphone, triflumuron, trimetacarb, tamidothion, XMC, xylylcarb, YI 5301/5302, zetamethrin.

Other known active compounds, for example herbicides or mixtures with fertilizers and growth regulators, are also possible.

The active compounds according to the invention may also be present in admixture with synergists in their commercially available formulations and in the use forms prepared from these formulations. Synergists are compounds that increase the action of the active compound without the need for the synergist added itself to be activated.

The active compound content of the use forms prepared from commercially available formulations can vary within considerable ranges. The concentration of the active compound of the use form 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 use form.

When used in hygienic pests and pests of stored products, the active compounds according to the invention show excellent residual activity against wood and clay and excellent stability against alkalis on lime surfaces.

The active compounds according to the invention are not only pests of plants, sanitary and stored agricultural products, but also animal parasites (external parasites), for example, ixodid ticks, argacid ticks, scabies mites mites, trombiculid mites, flies (biting or licking), parasitic fly larvae, veterinary medicines for teeth, hairy teeth, birds teeth and fleas. These parasites include:

Anoplurida , for example Haematopinus spp ., Linognathus spp ., Pediculus spp ., Pthirus spp ., Sole Novotes spp .

Hairs (Mallophagida) neck and arm assembly Serena (Amblycerina) and yiseukeu furnace Serena (Ischnocerina) suborder, such as tree Agate phone species (Trimenopon spp.), Agate phone species (Menopon spp.), Trinoton spp (teurino tone species. ), Bovicola spp ., Werneckiella spp ., Lepikentron spp ., Damalina spp ., Trichodectes spp ., Felicola spp .

Diptera and Nematocerina and Brachycerina subfamily, for example Aedes spp ., Anopheles spp ., Culex spp ., simul Solarium species (Simulium spp.), Yushi water Solarium species (Eusimulium spp.), play bottoming mousse species (Phlebotomus spp.), Lucho Mia species (Lutzomyia spp.), Cooley Koh des species (Culicoides spp.), chestnut Thorpe Crysops spp ., Hybomitra spp ., Atylotus spp ., Tabanus spp ., Haematopota spp ., Filippomia spp . Philipomyia spp .), Braula spp ., Musca spp ., Hydrotaea spp ., Stomoxys spp ., Haematobia spp . , Morellia spp ., Fannia spp ., Glossina spp ., Calliphora spp ., Lucil species ia spp .), Chrysomyia spp ., Wohlfartia spp ., Sarcophaga spp ., Oestrus spp ., Hypoderma spp . ), Gasterophilus spp ., Hyppobosca spp ., Lipoptana spp ., Melophagus spp .

Siphonapterida , for example Pulex spp ., Ctenocephalides spp ., Xenopsylla spp ., Ceratophyllus spp .

From the order of Heteropterida , for example Cimex spp ., Triatoma spp ., Rhodnius spp ., Panstrongylus spp .

Blattarida , for example Blatta orientalis , Periplaneta americana , Blatta germanica , Supella spp .

Mites; (. Ornithodorus spp) (Acarina Acarida) subclass and meta-and meso stigmasterol other (Meta and Mesostigmata) tree, for example, are the gas species (. Argas spp), ornithine Todo loose species, Ota Flavian species Otabius (spp .), ikso des species (Ixodes spp.), cancer Bulletin Mama species (Amblyomma spp.), bupil loose species (Boophilus spp.), der town centaur species (Dermancentor spp.), under the town killed less species (Haemaphysalis spp. ), Hyalomma spp ., Rhipicephalus spp ., Dermanyssus spp ., Raillietia spp ., Pneumonyssus spp . , Sternostoma spp ., Varroa spp .

Arc tine Dida (Actinedida) (Pro stigmasterol other (Prostigmata)) neck and Akari Dida (Acaridida) (O stigmasterol other (Astigmata)) tree, for example aka lapis species (Acarapis spp.), Cheil retina Cheyletiella (Ella species spp .), Ornithocheyletia spp ., Myobia spp ., Psorergates spp ., Demodex spp ., Trombicula spp . ), Listrophorus spp ., Acarus spp ., Tyrophagus spp ., Caloglyphus spp ., Hypodectes spp . ), Pterolichus spp ., Psoroptes spp ., Chorioptes spp ., Otodectes spp ., Sarcoptes spp . ), Notoedres spp ., Knemidocoptes spp ., Cytodites spp ., Laminosioptes spp .

The active compounds of general formula (I) according to the invention can also be used for farming livestock such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese and bees, and others. It is suitable for controlling pets such as arthropods that attack dogs, cats, birds in fish cages and fish tanks, and also so-called laboratory animals such as hamsters, guinea pigs, rats and mice. Controlling arthropods reduces deaths and yield reduction (for example in the production of meat, milk, wool, hides, eggs, honey), thus making the management of animals more economical and easier by using the active compounds according to the invention. Is possible.

The active compounds according to the invention are administered in the veterinary field in the form of tablets, capsules, solutions, potions, granules, pastes, cyclic agents, by intestinal administration, by means of mixing the drug into feeds and by suppositories, for example parenteral administration, eg For example by injection (intramuscular, subcutaneous, intravenous and intraperitoneal, etc.), in the form of insertions, by intranasal administration, for example in the form of dipping or dipping, spraying, swelling and dropping, washing and misting And in the form of shaped articles containing the active compounds, for example in the form of necklaces, ear tags, tail marks, leg bands, tethers or indicators, etc., in a known manner by transdermal administration.

When administered to livestock, poultry, pets, etc., the active compound of general formula (I) is directly or 100 as a preparation containing 1 to 80% by weight of the active compound (e.g. powders, emulsions, flowables). It can be used diluted to 10,000 times, or can be used as a chemical bath.

It has also been found that the compounds of general formula (I) according to the invention have potent pesticidal activity against insects which destroy industrial materials.

The following insects are mentioned as preferred examples and do not limit the invention:

Beetles, for example Hylotrupes bajulus , C hlorophorus 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 capu cins ), Heterobostrychus brunnes , Synoxylon spec . species, Dinoderus minutus

Der Marv Terrance (Dermapterans), for example, when Rex juben kusu (Sirex jubencus), right three loose exhaust gas (Urocerus gigas), right three loose exhaust gas tie the Taunus (Urocerus gigas taignus), right three loose brother rolls (Urocerus augur )

Termites , for example, Kalotermes flavicollis , Cryptotermes brevis , Heterotermes indicola , Reticulitermes flavipes , Reticulitermes santonensis , Reticulitermes lucifugus , Mastotermes darwiniensis , Zootermopsis nevadensis , Coff Coptotermes formosanus

Bristletails , for example Lepisma saccharina .

Industrial materials in this regard are understood in the sense of non-living materials, for example synthetic materials, adhesives, sizes, paper and board, leather, wood and wood products, and paints.

Materials which should be particularly preferably protected from attack of insects are wood and wood products.

Wood and wood products that can be protected by the compositions according to the invention or by mixtures containing such compositions are, for example, construction timber, wooden beams, railway sleepers, bridge components, byzantine bridges, wooden vehicles. Is understood to mean a box, pallet, container, telephone pole, wooden sign, window or door made of wood, plywood, chipboard, connector, or wood products commonly used in house construction or furniture.

The active compounds can be used, for example, in the form of concentrates or common conventional agents, for example powders, granules, solutions, suspensions, emulsions or pastes.

The mentioned formulations can be prepared by methods known per se, for example, the active compound by one or more solvents or diluents, emulsifiers, dispersants and / or binders or fixatives, waterproofing agents, drying agents and UV stabilizers, if appropriate, and coloring agents and pigments, if appropriate. And other processing aids.

The pesticidal compositions or concentrates used for protecting 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 that is used depends on the insect and the frequency and medium of the insect. Optimal use can be determined in each case by a series of tests. In general, however, it is sufficient to use from 0.0001 to 20% by weight, preferably 0.001 to 10% by weight of active compound, based on the material to be protected.

Solvents and / or diluents used are organic chemical solvents or solvent mixtures and / or oily or oil-type nonvolatile organic chemical solvents or solvent mixtures and / or polar organic chemical solvent mixtures or solvent mixtures and / or water and, if appropriate Emulsifiers and / or wetting agents.

Organic chemical solvents preferably used are oily or oily solvents having an evaporation number of at least 35 and a flash point of at least 30 ° C, preferably at least 45 ° C. Non-volatile, water-insoluble oily or oily solvents of this type are suitable mineral oils or their aromatic fractions, or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkyl. Benzene,

Materials that can be advantageously used are mineral oils having a boiling range of 170 to 220 ° C., white spirits having a boiling range of 170 to 220 ° C., spindle oils having a boiling range of 250 to 350 ° C., boiling ranges of 160 to 280 ° C. Petroleum or aromatic compounds, terpentine essences, and the like.

In a preferred embodiment, liquid aliphatic hydrocarbons having a boiling range of 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons having a boiling range of 180 to 220 ° C., and / or spindle oil and / or monochloronaphthalene, preferably Preferably α-monochloronaphthalene is used.

Organic non-volatile oily or oily solvents having an evaporation index of at least 35 and a flash point of at least 30 ° C., preferably at least 45 ° C., have solvent solvents also having an evaporation index of at least 35 and a flash point of at least 30 ° C., preferably at least 45 ° C. And if the pesticide / fungicide mixture is soluble or emulsifiable in this mixed solvent, it may be partially replaced with an organic solvent of high or medium volatility.

In a preferred embodiment, some of the organic chemical solvents or solvent mixtures are replaced with polar aliphatic organic chemical solvents or solvent mixtures. Materials which are preferably used are aliphatic organic chemical solvents with hydroxyl and / or ester and / or ether groups, for example glycol ethers, esters and the like.

Organic chemical binders used within the scope of the present invention are known per se and can be diluted with water and / or can be dissolved or dispersed or emulsified in the organic chemical solvent used, and / or synthetic resins, in particular acrylate resins. , Vinyl resins such as polyvinyl acetate, polyester resins, polycondensation or thickening resins, polyurethane resins, alkyd resins or modified alkyd resins, phenolic resins, hydrocarbon resins such as indene / coumarone Binders are used which consist of or contain a resin, silicone resin, dry vegetable oil and / or a physical dry binder based on dry oil and / or natural and / or synthetic resin.

Artificial resins used as binders can be used in the form of emulsions, dispersions or solutions. Up to 10% by weight bitumen or bituminous material may also be used as the binder. In addition, colorants, pigments, waterproofing agents, aromatic substances and inhibitors or corrosion inhibitors known per se can also be used.

The composition or concentrate according to the invention preferably contains at least one alkyd resin or modified alkyd resin and / or dry vegetable oil as an organic chemical binder. Preferably used according to the invention are alkyd resins having an oil content of at least 45% by weight, preferably 50 to 68% by weight.

All or some of the binders mentioned above may be replaced with fixatives (mixtures) or plasticizers (mixtures). These additives are intended to prevent volatilization, crystallization or precipitation formation of the active compound. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).

Plasticizers are phthalic acid esters such as dibutyl phthalate, dioctyl phthalate, or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid 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 acid esters Selected from the category.

The fixative is chemically based on polyvinyl alkyl ethers such as polyvinyl methyl ether, or ketones such as benzophenone or ethylenebenzophenone.

As solvents and diluents, water is particularly suitable, if appropriate, as a mixture with the abovementioned organic chemical solvents or diluents, emulsifiers and dispersants.

Particularly effective protection of wood is achieved by large scale industrial impregnation methods, for example vacuum, double vacuum or pressurized methods.

If suitable, the ready-to-use composition may further contain other pesticides and, if appropriate, one or more fungicides.

Further suitable components which can be mixed are preferably the pesticides or fungicides mentioned in WO 94/29 268. The compounds mentioned in this document are expressly incorporated by reference in this application.

Very particularly preferred components which can be mixed are insecticides, for example chlorpyriphos, bombardment, silafluorine, alphamethrin, cyfluthrin, cipermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flu Phenoxalone, hexaflumuron and triflumuron, and fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, ciproconazole, metconazole, imazaryl , Dichlorfluanid, tolylufluoride, 3-iodo-2-propynylbutyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazoline- 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 3.6 ml of 37% strength formaldehyde solution, 3.0 g of methyl glycinate hydrochloride (23.9 mmol) and 3.3 ml of triethylamine were dissolved in 30 ml of ethanol and heated at reflux for 5 hours.

The reaction mixture was cooled down and concentrated by evaporation of the solvent under reduced pressure. The residue was stirred with water and filtered off to dryness.

6,7-dihydro-1- (2-chloropyridin-5-yl-methyl) -6-methoxycarbonyl-methyl-8-nitro (5H) -imidazolidino- [2, at a melting point of 168 ° C. 8.9 g of 3-f] -pyrimidine were obtained.

Example 2

(Method b)

Of 6,7-dihydro-6-ethoxycarbonyl-methyl-8- (5H) -imidazolidino- [2,3-f] -pyrimidine (Example IV-1) in 20 ml of acetonitrile 1.5 g (5.86 mmol) were treated with 1.6 g potassium carbonate and 1.0 g (6.0 mmol) of 2-chloro-5-chloromethylthiazole. The reaction mixture was stirred at 40 ° C. for 6 hours. The insoluble material was then filtered off and the solution was evaporated to dryness. The residue was purified by column chromatography.

6,7-dihydro-1- (2-chlorothiazol-5-yl-methyl) -6-ethoxycarbonyl-methyl-8-nitro- (5H) -imidazolidino- [ 1.48 g of 2,3-f] -pyrimidine were obtained.

Preparation of Starting Material

2.0 g (20.2 mmol) of 2-nitromethylene-imidazolidine in 30 ml of ethanol together with 2.8 g (20.1 mmol) of ethylglycinate hydrochloride, 2.7 ml of triethylamine and 4 ml of 37% strength aqueous formaldehyde solution Mix and heat under reflux for 10 hours. The reaction mixture was cooled down and the solvent was concentrated by distillation. The residue was partitioned between water and diethyl ether and the organic phase was separated and dried over sodium sulfate and concentrated.

2.0 g of 6,7-dihydro-6-ethoxycarbonylmethyl-8-nitro- (5H) -imidazolidino- [2,3-f] -pyrimidine at a melting point of 155-158 ° C. was obtained.

According to the method of Examples 1 and 2 and according to general preparation instructions, the compounds of formula (I) listed in Table 1 below were obtained:

Table 1

(Continued Table 1)

(Continued Table 1)

^*) Lg. P = logarithm of partition coefficient P of material between solvent octanol and water, determined experimentally by reversed phase HPLC.

Compound of general formula (I)

A is Indicates.

Starting materials of the general formula (IV) listed in Table 2 below were obtained by the method of Example 2 and according to general preparation instructions:

TABLE 2

Example of use

In the following use examples, the compounds listed below were used as reference compounds:

(All compounds are disclosed in EP-A 0 247 477)

Example A

Phaedon Larva Test

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Cabbage leaves ( Brasica oleracea ) were treated by dipping into active compound formulations of the desired concentration and infected with mustard beetle larvae ( Peadon cocleariae ) while the leaves were damp.

After a certain period of time, the percent rescued was determined. 100% means that all the beetle larvae have been killed; 0% means that the beetle larva is not killed at all.

In this test, for example, the compounds of Preparation Examples 1, 3, 4, 7, 9, 10, 11, 12, 14, 19, 20, 22 and 23 are in each case at an exemplary active compound concentration of 0.001% After 3 days at 100%, the known compounds (A), (B), (C) and (E) exhibited no action but only 30% and only 40%. The salvage rate was shown and only 20% of the salvage rate was shown.

Example B

Flutella test

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Cabbage leaves ( Brasica oleracea ) were treated by immersion in the active compound formulation of the desired concentration and infected with cabbage moth ( Plutella maculipennis ) caterpillars while the leaves were moist.

After a certain period of time, the percent rescued was determined. 100% means that all caterpillars have been killed; 0% means that the caterpillar was not killed at all.

In this test, for example, the compounds of Preparation Examples 1, 6, 8, 9, 10, 11, 12, 13, 14, 15, 17, 19, 21 and 22 have an exemplary active compound concentration of 0.01%, After 3 days in each case, a 100% rescue rate was shown, while the known compound (E) had no action.

Example C

Spodoptera frugiperda test

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Cabbage leaves ( Brasica oleracea ) were treated by dipping into active compound formulations of the desired concentration, and infected with Oult's moth ( Spodoftera prujiferda ) caterpillars while the leaves were moist.

After a certain period of time, the percent rescued 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 Preparation Examples 8, 9, 10, 11, 12, 14, 15, 19 and 20 resulted in a 100% remedy after 3 days in each case at exemplary active compound concentrations of 0.001%. On the other hand, the known compounds (A), (D) and (F) did not show action, and (B), (C) and (G) showed only 30% rescue rate.

Example D

Nephotettix Exam

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Rice seedlings ( Oryzae sativa ) were treated by immersion in the active compound preparation at the desired concentration and infected with the larvae of the green rice leaf hopper ( Nephotettix cincticeps ) while the seedlings were moistened.

After a certain period of time, the percent rescued was determined. 100% means that all cicadas have been killed; 0% means that the tarnabis did not die at all.

In this test, compounds of Preparation Examples 6, 7, 8, 9, 10, 14, 15, 16, 17 and 18 were 100% rescued after 6 days in each case, at exemplary active compound concentrations of 0.0001% While the known compound (E) showed a rescue rate of only 20%.

Example E

Myzus Exam

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Vicia faba infected with Peach aphid ( Myzus percicae ) was treated by dipping into active compound formulation of the desired concentration and placed in a plastic dish.

After a certain period of time, the percent rescued was determined. 100% means that all peach aphids have been killed; 0% means that peach aphids are not killed at all.

In this test, the compounds of the following preparation examples were subjected to 1 = 99%, 4 = 80%, 6 and 16 = 90%, 15 = 98% and 20 after 1 day in each case at an exemplary active compound concentration of 0.001% While a rescue rate of = 100% was shown, known compounds (E) and (F) showed only 10% and no action, respectively.

Claims (12)

Tetrahydropyrimidine Derivatives of Formula (I): Where A is a group (Ia)-(CH ₂ ) m-COXR ¹ and (Ib) Represents one of Het represents pyridyl or thiazolyl mono- or di-substituted or unsubstituted by the same or different substituents selected from the group consisting of fluorine, chlorine and bromine, respectively, R ¹ represents benzyl mono- or di-substituted or unsubstituted by the same or different substituents selected from the group consisting of fluorine, chlorine, bromine and cyano, R ² represents C ₁ -C ₄ -alkyl or benzyl, X represents oxygen or the group -NH-, m represents an integer of 1 to 8, n represents the integer of 0 or 1. a) reacting the nitromethylene derivative of formula (II) with an amine of formula (IIIa) or (IIIb) in the presence of 2 to 4 times the molar amount of formaldehyde, or b) Preparation of a tetrahydropyrimidine derivative of formula (I) according to claim 1 characterized in that the nitropyrimidine derivative of formula (IV) is reacted with a compound of formula (V) in the presence of a base. Way: H ₂ N- (CH ₂ ) _m -CO-XR ¹ (IIIa) Het-CH ₂ -L (V) Where A is a group (Ia)-(CH ₂ ) m-COXR ¹ and (Ib) Represents one of Het represents pyridyl or thiazolyl mono- or di-substituted or unsubstituted by the same or different substituents selected from the group consisting of fluorine, chlorine and bromine, respectively, R ¹ represents benzyl mono- or di-substituted or unsubstituted by the same or different substituents selected from the group consisting of fluorine, chlorine, bromine and cyano, R ² represents C ₁ -C ₄ -alkyl or benzyl, X represents oxygen or the group -NH-, m represents an integer of 1 to 8, n represents an integer of 0 or 1, L is an anionic leaving group. Nitropyrimidine Derivatives of Formula (IV): Where A is a group (Ia)-(CH ₂ ) m-COXR ¹ and (Ib) Represents one of R ¹ represents benzyl mono- or di-substituted or unsubstituted by the same or different substituents selected from the group consisting of fluorine, chlorine, bromine and cyano, R ² represents C ₁ -C ₄ -alkyl or benzyl, X represents oxygen or the group -NH-, m represents an integer of 1 to 8, n represents the integer of 0 or 1. Formula (IV) according to claim 3, characterized in that the nitromethylene derivative of formula (IIa) is reacted with an amine of formula (IIIa) or (IIIb) in the presence of two to four times the amount of formaldehyde. Process for the preparation of nitropyrimidine derivatives of: H ₂ N- (CH ₂ ) _m -CO-XR ¹ (IIIa) Where n represents an integer of 0 or 1, R ¹ , R ² , X and m are as defined in claim 3. A pesticide, characterized in that it comprises tetrahydropyrimidine of general formula (I) according to claim 1. A pest control method according to claim 1, wherein the tetrahydropyrimidine of the general formula (I) acts on the pest or its habitat. A method for producing a pesticide, characterized in that the tetrahydropyrimidine of the general formula (I) according to claim 1 is mixed with an extender, a surfactant or an extender and a surfactant. The method of claim 2, wherein step a) is reacted in the presence of at least one substance selected from the group consisting of acid catalyst, diluent and base. The process of claim 2 wherein step a) is characterized in that the amine of formula (IIIa) or (IIIb) is in the form of a hydrohalide. The method of claim 2 wherein step b) is reacted in the presence of a diluent. The method of claim 4, wherein the reaction is carried out in the presence of at least one substance selected from the group consisting of an acid catalyst, a diluent and a base. The method of claim 4 wherein the amine of formula (IIIa) or (IIIb) is in the form of a hydrohalide.