DE3326509A1 - Substituted furazanes - Google Patents

Abstract

The invention relates to substituted furazanes of the formula (I) <IMAGE> in which R and R1 are identical or different and represent optionally substituted aromatic or heteroaromatic radicals, R<2> represents hydrogen, an OH or COOH group, or optionally substituted radicals from the series comprising alkyl, alkoxy, cycloalkyl, cycloalkenyl, alkoxycarbonyl, alkoxythiocarbonyl, alkylsulphonyl arylsulphonyl or aralkyl, Y represents oxygen, an S(O)m, -CR<3>R<4>, CO or -NR<5> group, in which m represents the numbers 0, 1 or 2, R<3>, R<4> and R<5> are identical or different and represent hydrogen or alkyl, n represents the numbers 0 or 1 and X represents oxygen or sulphur, which can be used as pesticides, in particular as acaricides and insecticides.

Description

Substituted furazans

The invention relates to substituted furazans, processes for their Manufacture and their use as pesticides, especially as Insecticides and acaricides.

It is not yet known that substituted furazans can be used as pesticides can be used, so far it is only known that certain heterocycles such as 3-phenyl-2-phenylimino-4,5-bis (trfluoromethylimino) thiazolidine, insecticides Have properties (see e.g. DE-AS 2 062 348).

It has now been found that the substituted furazans of the formula (I) in which R and R¹ are the same or different and represent optionally substituted aromatic or heteroaromatic radicals, R2 represents hydrogen, an OH or COOH group or optionally substituted radicals from the group consisting of alkyl, alkoxy, cycloalkyl, cycloalkenyl, alkoxycarbonyl, alkoxythiocarbonyl, Alkylsulfonyl, arylsulfonyl or aralkyl, Y stands for oxygen, an S (O) m ~, -CR3R4-, CO- or -NR5 grouping, in which m stands for the numbers 0, 1 or 2, R3 equals R4 and R5 or are different and stand for hydrogen or alkyl, n stands for the numbers 0 or 1 and X stands for oxygen or sulfur, can be used as pesticides, in particular as acaricides and insecticides.

The new substituted furazans of the formula (Ia) have also been found, in which R and R1 are the same or different and represent optionally substituted aromatic or heteroaromatic radicals, R2 represents hydrogen, an OH or COOH group, or optionally substituted radicals from the group consisting of alkyl, alkoxy, cycloalkyl, cycloalkenyl, alkoxycarbonyl, alkoxythiocarbonyl , Alkylsulfonyl, arylsulfonyl or aralkyl, Y stands for oxygen, an S (O), - r -CR R -, CO or NR5 group, in which m stands for the numbers 0, 1 or 2, R3, R4 and R5 are identical or different and stand for hydrogen or alkyl, n stands for the numbers 0 or 1 and X stands for oxygen or sulfur, where when R stands for phenyl, R1 stands for phenyl, R2 stands for hydrogen and X stands for oxygen or sulfur , in these cases n stands for the number 1, or when n stands for the number 0, R stands for 4-bromophenyl, R1 stands for 4-chlorophenyl and R2 stands for hydrogen, in this case X stands for sulfur.

It has also been found that the new substituted furazans of the formula (Ia) are obtained by a) 3-amino-1,2,5-oxadiazoles of the formula (II) in which Y, R and n have the meanings given above for formula Ia, with iso (thio) cyanates of the formula (III) R NCX (III) in which R1 and X have the meanings given above for formula Ia, optionally in the presence of Converts catalysts and, if appropriate, in the presence of diluents, or b) 3-iso (thio) cyanato-1,2,5-oxadiazoles of the formula (IV), in which X, Y, R and n have the meanings given above for formula Ia, with amines of the formula (V), NHR1R2 (V) in which R1 and R2 have the meanings given above for formula Ia, optionally in the presence of catalysts and optionally reacted in the presence of diluents.

The optionally substituted alkyl R2 is straight-chain or branched alkyl having 1 to 12, preferably 1 to 6, in particular 1 to 4 carbon atoms.

Examples are optionally substituted methyl, ethyl, n-propyl ' i-propyl, n-butyl, i-butyl, sec-butyl and tert. -Butyl called.

The optionally substituted alkoxy R2 is straight-chain or branched alkoxy having 1 to 12, preferably 1 to 6, in particular 1 to 4 carbon atoms.

Examples are optionally substituted methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, sec-butoxy and tert-butoxy called.

Cycloalkyl is optionally substituted cycloalkyl R2 preferably 3 to 8, in particular 3, 5 or 6 carbon atoms. Be exemplary optionally substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or Called cycloheptyl.

An optionally substituted cycloalkenyl R2 is preferably Cycloalkenyl with 5 or 6 carbon atoms and or 2 double bonds. Exemplary are optionally substituted cyclohexenyl, cyclopentenyl, cyclohexadienyl and called cyclopentadienyl.

Optionally substituted alkoxycarbonyl or alkoxythiocarbonyl R2 in the alkyl part preferably contain 1 to 4 carbon atoms, in particular 1 to 2 carbon atoms, it being possible for the alkyl part to be straight-chain or branched. Examples are optionally substituted methoxy, ethoxy, n-propoxy and Called i-propoxycarbonyl or -thiocarbonyl.

The optionally substituted alkylsulfonyl R2 is straight-chain or branched alkylsulfonyl having preferably 1 to 6, in particular 1 to 4 carbon atoms in the alkyl part. Examples are optionally substituted methyl, ethyl, called n-propyl-, i-propyl-, n-butyl-, i-butyl-, sec-butyl- and tert-butylsulfonyl.

Optionally substituted aralkyl R2 is Aralkyl substituted in the aryl part and / or alkyl part with preferably 6 or 10, in particular 6 carbon atoms in the aryl part and preferably 1 to 4 in particular 1 or 2 carbon atoms in the alkyl part, the alkyl part being straight-chain or branched can be.

Optionally substituted benzyl or phenylethyl are exemplary called.

Optionally substituted arylsulfonyl R2 preferably contains 6 or 10 carbon atoms in the aryl part, with optionally substituted naphthylsulfonyl and phenylsulfonyl, preferably phenylsulfonyl, may be mentioned.

R2 is preferably hydrogen.

Optionally contain substituted aromatic radicals R and R1 preferably 6 or 10 carbon atoms in the aryl part. Examples may be substituted phenyl or naphthyl, especially phenyl, called.

As optionally substituted heteroaromatic radicals R and R1 are 5-, 6- or 7-membered, preferably 5- or 6-membered rings with preferably 1 to 3, in particular 1 or 2, identical or different heteroatoms. As heteroatoms are oxygen, sulfur and / or nitrogen. Examples may be substituted furyl, thiophenyl, pyrazolyl, imidazolyl, pyrrolyl, 1,2,4- and 1,2,3-triazolyl, 1,2,3-, 1,2,4- and 1,3,5-triazinyl, pyrimidinyl, pyridinyl, oxazolyl, isoxazolyl, Thiazolyl and isothiazolyl, especially pyridinyl and pyrimidinyl mentioned.

4 5 The alkyl radicals R3, R and R are identical or different and can be straight-chain or branched. Preferential they contain 1 up to 8, especially 1 to 4 carbon atoms. Examples are methyl, ethyl, n- and i-propyl and n-, sec-, iso- and tert-butyl called.

Preferably R and R¹ are optionally substituted phenyl.

The substituted radicals mentioned in the definition of R, R¹ and R² can be one or more, preferably 1 to 3, in particular 1 or 2 identical or carry different substituents. Examples of substituents for R, R1 and R2 are listed: halogen, preferably fluorine, chlorine, bromine and iodine, especially fluorine, Chlorine and bromine; Alkyl with preferably 1 to 4, in particular 1 or 2 carbon atoms, such as methyl, ethyl, n- and i-propyl, n-, i-, sec- and tert-butyl; Alkoxy with preferably 1 to 4, especially 1 or 2 carbon atoms, such as methoxy, ethoxy, n- and i-propoxy, n-, i-, sec- and tert-butoxy; Alkylthio with preferably 1 to 4, especially 1 or 2 carbon atoms, such as methylthio, ethylthio, n- and i-propylthio, n-, i-, sec- and tert-butylthio; Cyano and / or nitro.

The radicals R and R1 can also be used as substituents by way of example are mentioned: haloalkyl, haloalkoxy and haloalkylthio with preferably in each case 1 to 4, in particular 1 or 2 carbon atoms and preferably 1 to 5, in particular 1 to 3 halogen atoms, the halogen atoms being identical or different divorced are and as halogen atoms, preferably fluorine, chlorine and / or bromine, in particular Fluorine and / or chlorine, such as trifluoromethyl, trifluoromethoxy, trifluoromethylthio, Chlorotrifluoroethoxy, tetrafluoroethoxy, trifluoroethoxy, difluorotrichloroethoxy, dichlorodifluoroethoxy, Hexafluoro-n-propoxy, chlorodifluoromethoxy and chlorodifluoromethylthio; and / or where applicable halogen-substituted C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-alkoxycarbonyl-C1 -C2-alkyl and C1-C4-alkoxycarbonyl-C1-C4-alkylthio; and / or possibly by Fluorine, chlorine and / or methyl substituted C1-C3-alkylene radical, which is 1 or 2 Contains oxygen atoms, and / or optionally by halogen, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, halogen-C1-C2-alkyl, halogen-C1-C2-alkoxy, halogen-C1 -C2-alkylthio, C1-C4-alkoxy-C1-C2-alkyl, C1-C4-alkylthio-C1-C2-alkyl and / or C1-C4-alkoxycarbonyl or a C1-C3-alkylene radical which is interrupted by 1 or 2 oxygen atoms is and optionally one or more times by fluorine, chlorine and / or methyl may be substituted, substituted phenoxy; and / or optionally by halogen, C1-C4-alkyl, halo-C1-C2-alkoxy and halo-C1-C2-alkyl substituted pyridin-2-yloxy; and / or optionally by C1-C4-alkyl, C3-C6-cycloalkyl, halogen-C1-C4-alkyl and phenyl, which can optionally be substituted one to three times by C1-C2-alkyl, C1-C2-alkoxy, C1 -C, -alkoxy, -C2-alkylthio, halo- gen-C1-C2-alkyl, halogen-C1-C2-alkoxy, Halogen-C1-C2-alkylthio, fluorine, chlorine and / or bromine can be substituted, substituted Pyrimidin-5-yloxy.

Halogen means (unless otherwise stated) fluorine, chlorine, bromine and / or Iodine, preferably fluorine, chlorine and / or bromine.

When n is 0, this means that R is directly on the oxadiazole ring is bound.

X preferably stands for oxygen and the index n for the number 0.

The new compounds of the formula (Ia) have properties which allow their use as pesticides, in particular draw they are characterized by an excellent insecticidal and acaricidal effectiveness. To the They also show some fungicidal action, in particular against Pyricularia oryzae and Pellicularia sasakii in rice.

The new substituted furazans of the formula (Ia) are preferred in which R and R1 are identical or different and optionally for substituted aryl with 6 to 1-0 carbon atoms or for one optionally substituted 5- to 7-membered heterocyclic aromatic ring with 1 to 3 identical or different heteroatoms, where the heteroatoms are oxygen, Are sulfur and / or nitrogen, R2 is hydrogen, an OH or COOH group or for optionally by halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, Cyano and / or nitro-substituted radical from the series alkyl or alkoxy, each with 1 to 6 carbon atoms in the alkyl part, cycloalkyl with 3 to 6 carbon atoms, Cycloalkenyl with 3 to 6 carbon atoms and 1 or 2 double bonds, alkoxycarbonyl and alkoxythiocarbonyl each having 1 to 6 carbon atoms in the alkyl part, alkylenesulfonyl with 1 to 6 carbon atoms in the alkyl part, arylsulfonyl with 6 to 10 carbon atoms in the aryl part and aralkyl with 6 to 10 carbon atoms in the aryl part and 1 to 2 Carbon atoms in the alkyl part.

Y stands for oxygen, an S (O), -, -CR R -, CO or NR5 group, in which m stands for the numbers 0, 1 or 2 and R3, R4 and R5 are identical or different are and represents hydrogen or alkyl having 1 to 6 carbon atoms, n represents the Numbers 0 or 1 and X is oxygen or sulfur, where when R is Is phenyl, R1 is phenyl, R2 is hydrogen, and X is oxygen or sulfur, in these cases n is the number 1, or when n is the Number 0 stands, R stands for 4-bromophenyl, R1 stands for 4-chlorophenyl, and R stands for hydrogen stands, in this case X stands for sulfur.

The new substituted furazans of the formula are particularly preferred (Ia), in which R is optionally represented by halogen, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, halo-C1-C4-alkyl, halo-C1-C4-alkoxy, halo-C1-C4 -Alkylthio, halogen-C1-C4-alkylcarbonyl, C1-C4-alkylcarbonyl, halogen-C1-C4 -alkoxycarbonyl, C1-C4-alkoxycarbonyl, C1-C4-alkoxycarbonyl-C1-C2-alkyl and / or C1-C4-alkoxycarbonyl-C1-C4-alkylthio substituted radicals from the series phenyl, pyridinyl, pyrimidinyl, 1,2,3-, 1,2,4- and 1,3,5-triazinyl, R1 represents radicals from the series phenyl, pyridyl, pyrimidinyl, 1,2,3-, 1,2,4- and 1,3,5-triazinyl, which may be substituted by Residues from the series halogen, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, Halo-C1-C4-alkyl, halo-C1-C4-alkoxy, halo-C1-C4-alkylthio, halo-C1 -C4-alkylcarbonyl, C1-C4-alkylcarbonyl, halogen-C1 -C4 -alkoxycarbonyl, C1-C4-alkoxycarbonyl-C1-C2-alkyl, C1-C4-alkoxycarbonyl-C1-C 4-alkylthio, and / or an optionally by fluorine, Chlorine and / or methyl substituted C1-C3-alkylene radical which has 1 or 2 oxygen atoms contains, and / or a phenoxy radical, which in turn is replaced by halogen, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, halogen-C1-C4-alkyl, halogen-C1-C4-alkoxy, Halogen-C1-C4-alkylthio, C1-C4-alkoxy-C1-C2-alkyl, C1-C4-alkylthio-C 'C2' C1-C4-alkoxycarbonyl and / or 1 2-alkyl, C -C one optionally by fluorine, chlorine and / or methyl substituted C1-C 3 -alkylene radical which contains 1 or 2 oxygen atoms substituted can be, and / or a pyridin-2-yloxy radical, which in turn is replaced by halogen, C1-C4-alkyl, halogen-C1-C2-alkoxy and / or halogen-C1-C2-alkyl can be substituted can, and / or a pyrimidin-5-yloxy radical, which in turn is replaced by C1-C2-alkyl, C1-C2-alkoxy, C1-C2-alkylthio, halo-C1-C2-alkyl, halo-C1-C2-alkoxy, halo-C1 -C2-alkylthio, fluorine, chlorine and / or bromine can be substituted, R2 for hydrogen, an OH or COOH group or optionally by fluorine, chlorine, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-alkylthio, cyano and / or nitro-substituted radicals from the Series C1-C4-alkyl, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl with 1 or 2 double bonds, C1-C4-alkoxycarbonyl, C1 -C4-alkoxythiocarbonyl, C1 -C4-alkylsulfonyl, Phenylsulfonyl, benzyl and phenylethyl, Y stands for oxygen, an S (O), r -CR³R4-, CO or NR5 group in which m stands for the numbers 0, 1 or 2, R3r R4 and R5 stand for hydrogen or C1-C4-alkyl, n stands for the numbers 0 or 1 and X stands for oxygen or sulfur, where if R for phenyl R1 is phenyl, R2 is hydrogen, and X is oxygen or Is sulfur, in these cases n is the number 1, or when n is the number 0 is, R is 4-bromophenyl, R1 is 4-chlorophenyl, and R2 is hydrogen stands, in this case X stands for sulfur.

The new substituted furazans are very particularly preferred of the formula (Ia), in which R represents radicals from the series phenyl, pyridin-2-yl, pyrimidin-2-yl, 1,2,4-triazin-2-yl and 113,5-triazin-2-yl, which can be substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, ethoxy, methylthio, Trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methylcarbonyl, methoxycarbonyl, Ethoxycarbonyl, n-butoxycarbonyl, tert. -Butoxycarbonyl, methoxycarbonylmethyl, Ethoxycarbonylmethyl, methoxycarbonylmethylthio and / or ethoxycarbonylmethylthio, R1 stands for phenyl, which can be substituted by radicals from the series fluorine, Chlorine, bromine, nitro, cyano, methoxy, ethoxy, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, methylthio, ethylthio, trifluoromethyl, trifluoromethoxy, Difluoromethyl, difluoroethyl, pentafluoroethyl, difluoromethoxy, chlorodifluoromethoxy, Chlorotrifluoroethoxy, tetrafluoroethoxy, dichlorodifluoroethoxy difluorotrichloroethoxy, Hexafluoropropoxy, trifluoromethylthio, difluoromethylthio, chlorodifluoromethylthio, Chlorotrifluoroethylthio, hexafluoropropylthio, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, sec. -Butoxycarbonyl, tert-butoxycarbonyl, Trifluoroethoxycarbonyl, methylcarbonyl, methoxycarbonylmethyl, methoxycarbonylethyl, Ethoxycarbonylmethyl, difluoromethylenedioxy, ethylenedioxy, chlorotrifluoroethylenedioxy, Difluoroethylenedioxy, methylenedioxy, trifluoroethylenedioxy, difluoromethyleneoxydifluoromethyleneoxy, Tetrafluoroethylene dioxy, 2-methyl-1,1,2-trifluoroethylene dioxy, 2,2-dimethylethyleneoxy and / or a phenoxy radical, which in turn is optionally replaced by chlorine, bromine, nitro, Cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, Methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, sec.-butoxy, tert.-butoxy, Trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoroethyl, pentafluoroethyl, difluoromethoxy, Chlorodifluoromethoxy chlorotrifluoroethoxy, Tetrafluoroethoxy, dichlorodifluoroethoxy, Difluorotrichloroethoxy, hexafluoropropoxy, trifluoromethylthio, difluoromethylthio, Chlorodifluoromethylthio, chlorotrifluoroethylthio, hexafluoropropylthio, methoxymethyl, Ethoxymethyl, methylthiomethyl, ethylthiomethyl methoxycarbonyl ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, difluoromethylenedioxy, ethylenedioxy, chlorotrifluoroethylenedioxy, Difluoroethylene dioxy, methylenedioxy, trifluoroethylene dioxy, difluoromethylene oxydifluoromethyleneoxy Tetrafluoroethylene dioxy, 2-methyl-11, 2-trifluoroethylene dioxy and / or 2,2-dimethylethyleneoxy is substituted, and / or a pyridin-2-yloxy radical, which in turn is optionally substituted by chlorine, bromine, methyl, trifluoromethyl and / or trifluoromethoxy is, and / or a pyrimidin-5-yl-oxy radical, which in turn optionally by methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, Chlorine and / or bromine is substituted, R2 represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl or sec-butyl, Y stands for oxygen, an S (O) m-, CR³R4, CO or NR5 group, in which m is 0, 1 or 2, R3, R4 and R5 stand for hydrogen or methyl, n stands for the numbers 0 or 1 and X stands for oxygen or sulfur, where when R is phenyl, R1 represents phenyl, R2 represents hydrogen, and X represents oxygen or sulfur stands, in these cases n stands for the number 1, or if n stands for the number 0, R stands for 4-bromophenyl, R1 stands for 4-chlorophenyl, and R2 stands for hydrogen, in this case X stands for sulfur.

Of particular interest are those compounds of the formula (Ia), in which R for optionally by fluorine, chlorine, bromine, cyano, nitro, methyl, Methoxy and / or methylthio-substituted phenyl, R1 is a phenyl radical stands, which optionally by chlorine, bromine, nitro, cyano, methoxy, methylthio, Methyl, Trifluoromethyl, trifluoromethoxy, trifluoromethylthio, difluoromethoxy, chlorodifluoromethoxy Chlorotrifluoroethoxy, tetrafluoroethoxy, dichlorodifluoroethoxy, difluorotrichloroethoxy, Hexafluoro-npropoxy, difluoromethylthio, chlorodifluoromethylthio, chlorotrifluoroethylthio, Hexafluorpropylthio, ethoxycarbonyl, n-propoxycarbonyl, n-butoxycarbonyl, tert. Butoxycarbonyl, difluoromethylenedioxy, chlorotrifluoroethylenedioxy, difluoroethylenedioxy, Trifluoroethylene dioxy, tetrafluoroethylene dioxy, difluoromethylene oxydifluoromethyleneoxy, 2,2-dimethyl-ethyleneoxy and / or a phenoxy radical, which in turn may be by chlorine, bromine, nitro, cyano, methyl, tert-butyl, methoxy, ethoxy, n-propoxy, i-propoxy, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methoxymethyl, methylthiomethyl, Ethoxymethyl, ethylthiomethyl and / or 2,2-dimethylethyleneoxy is substituted, and / or a pyridin-2-yloxy radical, which in turn is replaced by chlorine, methyl, methoxy, Trifluoromethyl and / or trifluoromethoxy can be substituted, R² for hydrogen or methyl, Y is oxygen, an S (O), r CR³ R4, CO or NR5 group stands in which m stands for 0, 1 or 2, R3, R4 and R5 for hydrogen or methyl stand, n stands for the numbers 0 or 1 and X stands for oxygen or sulfur, whereby when R is phenyl, R1 is phenyl, R2 is hydrogen and X is Is oxygen or sulfur, in these cases n is the number 1, or if n stands for the number 0, R stands for 4-bromophenyl, R1 stands for 4-chlorophenyl, and R stands for hydrogen, in this case X stands for sulfur.

Those compounds of the formula are of very particular interest (Ia), in which R for optionally by fluorine, chlorine, bromine, cyano, nitro, methyl, Methoxy and / or methylthio-substituted phenyl, R1 is a phenyl radical stands, which is optionally substituted by chlorine, trifluoromethyl, trifluoromethylthio, Trifluoromethoxy, difluorodichloro- ethoxy, chlorotrifluoroethoxy, tetrafluoroethoxy, Difluorotrichloroethoxy and / or a phenoxy radical, which in turn may be by chlorine, nitro, cyano, methoxy, ethoxy, n-propoxy, i-propoxy, methyl, trifluoromethyl, Trifluoromethoxy, trifluoromethylthio, methoxymethyl, methylthiomethyl, ethylthiomethyl and / or 2,2-dimethyl-ethyleneoxy is substituted, and / or a pyridin-2-yloxy radical, which in turn, optionally by chlorine, trifluoromethyl and / or trifluoromethoxy is substituted, R2 is hydrogen, n is the number 0 and X is oxygen stands, where when R stands for phenyl, R1 stands for phenyl, and R2 stands for hydrogen stands, in this case n stands for the number 1, or when R stands for 4-bromophenyl, R1 represents 4-chlorophenyl, and R2 represents hydrogen, in this Case X is sulfur.

If, according to process variant (a), 3-amino-4-phenyl-1,2,5-oxadiazole and 4- (4-chlorophenoxy) phenyl isocyanate are used as starting materials, the course of the reaction can be represented by the following equation: If, according to process variant (b), 4- (4-chlorophenyl) -3-isocyanato-1,2,5-oxadiazole and 4- (4-trifluoromethylphenoxy) aniline are used as starting materials, the course of the reaction can be represented by the following equation: The 3-amino-1,2,5-oxadiazoles of the formula (II) to be used as starting materials are known and / or can be prepared by processes and methods known from the literature (cf. J. Prakt. Chem. 315, 4, page 791 - 795 (1973)). The amino group can be converted into the isocyanate or iso-thio-cyanate group by conventional methods, e.g. by reaction with phosgene or thiophosgene in diluents such as toluene and / or pyridine, at a temperature between -200C to + 500C ( see.

Manufacturing example). The compounds of formula (in) based on this Ways are obtained are new.

The present invention includes the new compounds of the formula (1V), in which R, Y, n and X have the meanings given above for formula I.

The compounds of the formulas (III) and (V) are known and / or are not known can be produced by processes and methods known from the literature (cf. DE-OS 2 748 636, DE-OS 3 033 512 and EP 0 057 888).

The diluents used in the process according to the invention are (variants (a) and (b)) practically all inert organic solvents in question. These include in particular aliphatic and aromatic, optionally halogenated hydrocarbons, such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, Xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl and dibutyl ethers, glycol dimethyl ether and Diglycol dimethyl ether, tetrahydrofuran. And dioxane, ketones such as acetone, methyl ethyl, Methyl isopropyl and methyl isobutyl ketone, esters such as methyl acetate and ethyl acetate, Nitriles such as acetonitrile and propionitrile, amides such as dimethylacetamide and N-methyl-pyrrolidone, and tetramethylene sulfone.

Process variants can be used as catalysts for the reaction (a) and (b) preferably tertiary amines, such as triethylamine and 1,4-diazabicyclo / 2, 2, 27-octane, as well as organic tin compounds such as dibutyltin dilaurate are used will.

The reaction temperature can vary within a relatively wide range will. In general, process variant a) is used between 20 and 1800C, preferably between 40 and 1200C and in process variant b) between 20 and 200 ° C., preferably between 60 and 1900 ° C. The process variants according to the invention are generally carried out at normal pressure.

To carry out the process variants according to the invention the starting materials are usually used in approximately equimolar amounts. An excess one or the other reaction component brings no significant advantages.

The reaction products are worked up by customary methods, e.g. by sucking off the precipitated product or by removing unwanted ones By-products from the reaction mixture. The melting point is used for characterization.

The active ingredients are suitable and cheaper if they are well tolerated by plants Warm-blooded toxicity for the control of animal pests, especially insects, Arachnids and nematodes, which are used in agriculture, in forests, in storage and material protection as well as in the hygiene sector. You are against normal sensitive and resistant species as well as against all or individual stages of development effective. The pests mentioned above include: From the order of the Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio schaber From the order of Diplopoda e.g. Blaniulus guttulatus.

From the order of the Chilopoda, e.g. Geophilus carpophagus and Scutigera spec.

From the order of the Symphyla, e.g. Scutigerella immaculata.

From the order of the Thysanura e.g. Lepisma saccharina.

From the order of the Collembola, e.g. Onychiurus armatus.

From the order of the Orthoptera, e.g. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.

From the order of the Dermaptera, e.g. Forficula auricularia.

From the order of the Isoptera, e.g. Reticulitermes spp ..

From the order of the Anoplura e.g. Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp.r Linognathus spp.

From the order of the Mallophaga, for example Trichodectes spp., Damalinea spp.

From the order of the Thysanoptera, e.g. Hercinothrips femoralis, Thrips tabaci.

From the order of the Heteroptera, e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

From the order of the Homoptera, e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humulir, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. Psylla spp.

From the order of the Lepidoptera, e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp. Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.

From the order of the 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, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.

From the order of the Hymenoptera, for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp. Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.

From the order of the Siphonaptera, e.g. Xenopsylla cheopis, Ceratophyllus spp ..

From the order of the Arachnida, e.g. Scorpio maurus, Latrodectus mactans.

From the order of the Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp. r Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp.r Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..

The active ingredients can be converted into the usual formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granulates, aerosols, Active ingredient-impregnated natural and synthetic materials, fine encapsulation in polymers Substances and in coating compounds for seeds, also in formulations with fuel charges, such as smoking cartridges, cans, coils and the like, as well as ULV cold and warm smoke formulations.

These formulations are prepared in a known manner, for example by Mixing the active ingredients with extenders, i.e. liquid solvents, under Liquefied gases and / or solid carriers under pressure, possibly using surface-active agents, i.e. emulsifiers and / or dispersants and / or foam-generating agents. In the case of using water as an extender For example, organic solvents can also be used as auxiliary solvents. The following liquid solvents are essentially: aromatics, such as xylene, Toluene, or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic Hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic Hydrocarbons, such as cyclohexane or paraffins, e.g. petroleum fractions, alcohols, such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, Methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, as well as water; with liquefied gaseous extenders or carriers are meant liquids which are at normal temperature and are gaseous under normal pressure, e.g. aerosol propellants such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide; come as solid carriers in question: e.g. natural rock flour, such as kaolins, clays, talc, chalk, Quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, such as finely divided silica, aluminum oxide and silicates; as solid carriers for granulates are possible: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules made from inorganic and organic flours as well as granules made of organic material such as sawdust, coconut shells, Corn on the cob and tobacco gel; as an emulsifier and / or foam generator Agents are possible: e.g. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, Polyoxyethylene fatty alcohol ethers, e.g. alkylaryl polyglycol ethers, alkyl sulfonates, Alkyl sulfates, aryl sulfonates and protein hydrolysates; come as a dispersant in question: e.g. lignin sulphite waste liquors and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-like polymers are used such as gum arabic, polyvinyl alcohol, polyvinyl acetate.

Dyes such as inorganic pigments, e.g.

Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as Alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight Active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used in their commercially available formulations and in the use forms prepared from these formulations as a mixture with other active ingredients such as insecticides, attractants, sterilants, acaricides, nematicides, Fungicides, growth regulators or herbicides are present. To the insecticides include, for example, phosphoric acid esters, car- bamate, carboxylic acid ester, chlorinated hydrocarbons, phenylureas, produced by microorganisms Substances, etc.

The active ingredients according to the invention can also be used in their commercially available form Formulations and in the use forms prepared from these formulations present in a mixture with synergists. Synergists are connections through which the effect of the active ingredients is increased without the added synergist itself must be actively effective.

The active ingredient content of the prepared from the commercially available formulations Application forms can vary within wide ranges. The active ingredient concentration the use forms can contain from 0.0000001 to 95% by weight of active ingredient, preferably are between 0.0001 and 1% by weight.

They are used in a customary manner adapted to the use forms Way.

When used against hygiene and storage pests stand out the active ingredients through an excellent residual effect on wood and clay as well as through good alkali stability on limed substrates.

The active compounds according to the invention are also suitable for combating Insects, mites, ticks, etc. in the field of animal husbandry and cattle breeding, whereby better results by controlling the pests, e.g.

higher milk yield, higher weight, nicer Animal fur, longer life, etc. can be achieved.

The active ingredients according to the invention are applied to these Areas in a known manner, such as by external application in the form, for example of immersion (dipping), spraying (spaying), pour-on and spot-on -and of powdering.

The biological effectiveness of the compounds according to the invention should are explained using the following examples.

Example A Laphygma test Solvent: 3 parts by weight of dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether Active ingredient preparation is mixed 1 part by weight of active ingredient with the specified Amount of solvent and the specified amount of emulsifier and dilutes the concentrate with water to the desired concentration.

Cabbage leaves (Brassica oleracea) are dipped in the active ingredient preparation of the desired concentration and treated with caterpillars of the owl moth (Laphygma frugiperda) occupied as long as the leaves are still moist.

After the desired time, the destruction is determined in%. Thereby means 100% that all caterpillars have been killed; 0% means that none of the caterpillars have been killed became.

In this test, for example, at a concentration of 0.1%, for example the compound of preparation example (5) had a kill of 100 after 7 days %.

Example B Test with Lucilia cuprina resistant larvae emulsifier: 35 Parts by weight of ethylene glycol monomethyl ether 35 parts by weight of nonylphenol polyglycol ether To produce an appropriate preparation of the active ingredient, mix three parts by weight Active ingredient with seven parts by weight of the above mixture and diluted the concentrate thus obtained with water to the desired concentration in each case.

About 20 Lucilia cuprina res. -Larvae are placed in a test tube, which contains approx. 1 cm3 horse meat and 0.5 ml of the active ingredient preparation. To The degree of destruction is determined for 24 hours.

This test showed, for example, at a concentration of 3,000 ppm For example, the compound of preparation example (8) had a kill of 100 %.

Example C Eisterility and Developmental Inhibition Test with Tetranychus urticae (common spider mite) Solvent: 3 parts by weight of dimethylformamide emulsifier : 1 part by weight of alkylaryl polyglycol ether To make a Appropriate active ingredient preparation, 1 part by weight of active ingredient is mixed with the specified amount of solvent and the specified amount of emulsifier and diluted the concentrate with water to the desired concentrations.

The leaves of a bean plant (Phaseolus vulgaris) are dipped into the appropriately concentrated active ingredient preparation. After the active ingredient has dried on For preparation, the leaves are populated with female spider mites for about 16 hours to lay their eggs (approx. 50 eggs / repetition), The sum of the sterile and / or killed eggs and of the killed larvae, nymphs and dormant stages of a generation based on the The number of eggs laid gives the kill in t. 100% means that all Animals have been killed; 0% means that none of the animals have been killed.

In this test, for example, at an active ingredient concentration of 0.02% of the following compounds of Preparation Examples (1), (2), (5), (10), (33), (34), (35) and (38) kill 100% after 12 days.

Example D Developmental inhibition test with Tetranychus urticae (common spider mite) Solvent: 3 parts by weight of dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether To the To prepare an appropriate preparation of the active ingredient, mix 1 part by weight Active ingredient with the specified amount of solvent and the specified amount of emulsifier and dilute the concentrate with water to the desired concentrations.

The leaves of the bean plant (Phaseolus vulgaris), which are approx. 50 eggs of the common spider mite are occupied, one dips into the appropriately concentrated one Active ingredient preparation. The sum of the killed eggs, larvae, nymphs and resting stages one generation based on the number of eggs used gives the kill in%. 100% means that all animals have been killed; 0% means that there are no animals were killed.

In this test, for example, at an active ingredient concentration of 0.02% of the following compounds of Preparation Examples (1), (2), (5), (10), (33), (34), (35) and (38) kill 100% after 12 days.

The preparation of the compounds according to the invention is to be illustrated by the following preparation examples: Example 1: (Process variant a) 3.23 g (0.02 mol) of 3-amino-4-phenyl-1,2,5-oxadiazole are stirred in 100 ml of dry toluene at 60.degree. 4.92 g (0.02 mol) of 4- (4-chlorophenoxy) phenyl isocyanate and a drop of dibutyltin dilaurate are then added, and the mixture is refluxed for 5 hours. After cooling to 200 ° C., the product which has crystallized out is separated off, washed with toluene and dried.

6.8 g (83.5% of theory) N- / 4- (4-chlorophenoxy) -pheny7-N 'are obtained -4-phenyl-1,2,5-oxadiazol-3-yl) urea, melting point 1950C.

Example 2: (Process variant b) 2.53 g (0.01 mol) 4- (4-trifluoromethylphenoxy) aniline are dissolved in 60 ml of dry toluene at 60 "C. After adding 2.2 g (0.01 mol) 3- Isocyanato-4- (4-chlorophenyl) -1,2,5-oxadiazole in 10 ml of dry toluene is stirred for 30 minutes at 80 ° C. and most of the solvent is then distilled off.

3.6 g (76% of theory) of N-E4- (4-trifluoromethylphenoxy) are obtained -phen'yl7-N - / 4- (4-chlorophenyl) -1,2,5-oxadiazol-3-yl) urea of melting point 2080C.

The compounds of the formula (Ib) listed in Table 1 below are prepared analogously to Example 1 or 2 or process variant (a) or (b): Table 1: Example R6 R7 melting point Just. if 3 CL tFCl 226 4 CL OCF3 176 5 Clo CFCF3 186 6 ClO OSCF3 211 CL 7 Cl CF3 196 CL 8 Clo tOCF2-CHFCl 195 CL 9 Clo doCF2-CHF2 201 CL CL 10 CL tOtCF3 216 Cl Table 1 - continued Ex. R6 R7 Melting point No. R 0C CL 11 O tCF3 211 12 ClO oOOCl 219 13 d oo <3C l 205 CL 14 Cld oOOCl 206 / CF3 15 D 0 191 16 / CF3 16 217 Cl CF3 17 O 04 199 CF3 18 ClO 04 181 CF3 19 D DOOCl 202 20 O - oCF2-CHF2 199 21 CL OOCF2-CHF2 227 Table 1 - continued Ex. R6 R7 Melting point No. OC 22 k «O 0CF2 ~ CHFz 208 CL 23 b O 0CF2-ccl3 225 Cl Cl 24 (½c) oCF2-CHCL2 239 25 Cl O o 0CF2-Ccl3 256 CL 26 Cl o 4 OC F2-CHCl2 194 CL 27 O ~ d OCFz ~ CHCl2 207 28 CLZ G o ° ~ O 195 CH2-S-C2H5 29 Cl OO 0 9 199 OC3H7-iso 30 Cl oo O 9 190 0t H3C CH3 Table 1 - continued Ex. R6 R7 Melting point No. OC 31 Cl- 0 213 32 C lo 4 L 224 33 D 201 34 O 0 9 C l 196-197 CL 35 O oOOCF3 203 36 O OOOOCH3 202 37 D 192 37 H3C CH3 38 CL oOoOC F3 197 39 H3Ce OOCF2CHCl2 228-229 40 H3CO OOoCF3 182 Table 1 - continued No. R6 R7 melting point No. R6 OC 41 CL oo OQ CF3 206 Cl 42 Cl <O ob b Cl 249 43 CL 0CL 238 CL 44 CO - ((Cl O o O o CN 247 45 CL Ir i)> O \ (-NOz 229 46 H3CO o O SCF3 170 Starting products of the formula (IV): Example (IV-1) At 0OC to 50C, 50 g of phosgene are gassed into 400 ml of dry toluene. A solution of 58.7 g (0.3 mol) 3-amino-4- (4-chlorophenyl) -1,2,5-oxadiazole and 52.2 g (0 , 66 mol) of pyridine in 400 ml of toluene was added dropwise and the mixture was stirred at 30 ° C. for 2 hours. The precipitated salts are filtered off with suction with exclusion of moisture, the filtrate is concentrated and the residue is distilled in vacuo.

30.5 g (54.5% of theory) of 4- (4-chlorophenyl) -3-isocyanato-1,2,5-oxadiazole are obtained from boiling point bp2 .: 108 "C to 1120C.

The other compounds of the formula are obtained analogously to Example (IV-1) (IV) such as: 3-isocyanato-4-phenyl-1,2,5-oxadiazole (IV-2) of boiling point 850C.

Claims (10)

Claims Substituted furazans of the formula (Ia) in which R and R1 are the same or different and represent optionally substituted aromatic or heteroaromatic radicals, R2 represents hydrogen, an OH or COOH group, or optionally substituted radicals from the group consisting of alkyl, alkoxy, cycloalkyl, cycloalkenyl, alkoxycarbonyl, alkoxythiocarbonyl , Alkylsulfonyl, arylsulfonyl or aralkyl, Y stands for oxygen, an S (O) m -CR3R4 -, CO or NR5 group, in which m stands for the numbers 0, 1 or 2, R3, R4 and G5 are the same or are different and stand for hydrogen or alkyl, n stands for the numbers 0 or 1 and X stands for oxygen or sulfur, where when R stands for phenyl, 1 stands for phenyl, R2 R stands for hydrogen and X stands for oxygen or sulfur, in these cases n stands for the number 1, or when n stands for the number 0, R stands for 4-bromophenyl, R1 stands for 4-chlorophenyl and R2 stands for hydrogen, in this case X stands for sulfur. 2. Substituted furazans of the formula (Ia) according to claim 1, in which R and R1 are identical or different and represent optionally substituted aryl with 6 to 10 carbon atoms or for an optionally substituted 5- to 7-membered heterocyclic aromatic ring with 1 to 3 identical or different Heteroatoms, where the heteroatoms are oxygen, sulfur and / or nitrogen stand, R2 stands for hydrogen, an OH or COOH group or for optionally by halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, cyano and / or nitro-substituted radicals from the series alkyl or alkoxy, each with 1 to 6 carbon atoms in the alkyl part, cycloalkyl with 3 to 6 carbon atoms, Cycloalkenyl with 3 to 6 carbon atoms and 1 or 2 double bonds, alkoxycarbonyl and alkoxythiocarbonyl each having 1 to 6 carbon atoms in the alkyl part, alkylsulfonyl with 1 to 6 carbon atoms in the alkyl part, arylsulfonyl with 6 to 10 carbon atoms in the aryl part and aralkyl with 6 to 10 carbon atoms in the aryl part and 1 to 2 carbon atoms in the alkyl part, represents oxygen, an S (O), -CR³R4 -, CO-5 or NR group stands in which m stands for the numbers 0, 1 or 2 and 4 5 R3, R4 and R5 are the same or are different and represent hydrogen or alkyl having 1 to 6 carbon atoms stands, n stands for the numbers 0 or 1 and X stands for oxygen or sulfur, where if R c is phenyl, R¹ is phenyl, R² is hydrogen stands, and X stands for oxygen or sulfur, in these cases n stands for the number 1 or when n is the number 0, R is 4-bromophenyl, R1 is 4-chlorophenyl R2 stands for hydrogen, in this case X stands for sulfur. 3. Substituted furazans of the formula (Ia) according to claim 1, in which R. for optionally by halogen, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, Halo-C1-C 4-alkyl, halo-C1-C 4-alkoxy, halo-C1-C 4-alkylthio, halo-C1 -C4-alkylcarbonyl, C1 -C4-alkylcarbonyl, halogen-C1 -C4-alkoxycarbonyl, C1-C4-alkoxycarbonyl, C1-C4-alkoxycarbonyl-C1-C2-alkyl and / or C1-C4-alkoxycarbonyl-C1-C4-alkylthio substituted radicals from the series phenyl, pyridinyl, pyrimidinyl, 1,2,3-, 1,2,4- and 1,3,5-triazinyl, R¹ represents radicals from the series phenyl, pyridyl, pyrimidinyl, 1,2,3-, 1,2,4- and 1,3,5-triazinyl, which may be substituted by Residues from the series halogen, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, Halogen-C1-C4-alkyl, halogen-C1-C4-alkoxy, halogen-C1-C4-alkylthio, halogen-C1-C4-alkylcarbonyl, C1-C4-alkylcarbonyl, halogen-CI -C4-alkoxycarbonyl, CI -C4-alkoxycarbonyl-C1 -C2-alkyl, C1-C4-alkoxycarbonyl-C1-C 4-alkylthio, and / or an optionally by fluorine, Chlorine and / or methyl substituted C1-C3-alkylene radical which has 1 or 2 oxygen atoms contains, and / or a phenoxy radical, which in turn is replaced by halogen, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, halogen-C1-C4-alkyl, halogen-C1-C4-alkoxy, Halogen-C1-C4-alkylthio, C1-C4-alkoxy-C1-C2-alkyl, C1-C4-alkylthio-C1-C2-alkyl, C1-C4-alkoxycarbonyl and / or an optionally by fluorine, chlorine and / or methyl-substituted C1-C3-alkylene radical which has 1 or 2 oxygen atoms contains, may be substituted, and / or a pyridin-2-yloxy radical, which in turn substituted by halogen, C1-C4-alkyl, halogen-C1-C2-alkoxy and / or halogen-C1-C2-alkyl can be, and / or a pyrimidin-5-yloxy radical, which in turn is replaced by C1-C2-alkyl, C1-C2-alkoxy, C1-C2-alkylthio, halo-C1-C 2-alkyl, halo-C1-C2-alkoxy, halo-C1-C 2-alkylthio, fluorine, chlorine and / or bromine can be substituted, R2 for hydrogen, an OH or COOH group or optionally by fluorine, chlorine, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-alkylthio, cyano and / or nitro-substituted radicals from the Series C1-C4-alkyl, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl with 1 or 2 double bonds, C1-C4-alkoxycarbonyl, C1 -C4-alkoxythiocarbonyl, C1 -C4-alkylsulfonyl, Phenylsulfonyl, benzyl and phenylethyl, Y stands for oxygen, an S (O), - r -CR3R4-, CO or NR5 grouping, in which m stands for the numbers 0, 1 or 2, R3, R4 and R5 stand for hydrogen or C1-C4-alkyl, n stands for the numbers 0 or 1 and X stands for oxygen or sulfur, where when R is phenyl R1 is phenyl, R2 is hydrogen, and X is oxygen or Is sulfur, in these cases n is the number 1, or when n is the number 0 is, R is 4-bromophenyl, R1 is 4-chlorophenyl, and R2 is hydrogen stands, in this case X stands for sulfur. 4. Substituted furazans of the formula (Ia) according to claim 1, in which R for radicals from the series phenyl, pyridin-2-yl, pyrimidin-2-yl, 1,2,4-triazin-2-yl and -1,3,5-triazin-2-yl, which can be substituted by fluorine, chlorine, Bromine, cyano, nitro, methyl, ethyl, methoxy, ethoxy, methylthio, trifluoromethyl, Trifluoromethoxy, trifluoromethylthio, Methylcarbonyl, methoxycarbonyl, Ethoxycarbonyl, n-butoxycarbonyl, tert-butoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, Methoxycarbonylmethylthio and / or ethoxycarbonylmethylthio, R1 is phenyl, which can be substituted by radicals from the series fluorine, chlorine, bromine, nitro, Cyano, methoxy, ethoxy, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, methylthio, ethylthio, trifluoromethyl, trifluoromethoxy, difluoromethyl, Difluoroethyl, pentafluoroethyl, difluoromethoxy, chlorodifluoromethoxy, chlorotrifluoroethoxy, Tetrafluoroethoxy, dichlorodifluoroethoxy, difluorotrichloroethoxy, hexafluoropropoxy, Trifluoromethylthio, difluoromethylthio, chlorodifluoromethylthio, chlorotrifluoroethylthio, Hexafluoropropylthio, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, trifluoroethoxycarbonyl, Methylcarbonyl, methoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylmethyl, Difluoromethylenedioxy, ethylenedioxy, chlorotrifluoroethylenedioxy, difluoroethylenedioxy, Methylenedioxy, trifluoroethylene dioxy, difluoromethylene oxydifluoromethyleneoxy, tetrafluoroethylene dioxy, 2-methyl-1,1,2-trifluoroethylene dioxy, 2,2-dimethylethyleneoxy and / or a phenoxy radical, who in turn optionally by chlorine, bromine, nitro, cyano, Methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, methoxy, Ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, sec.-butoxy, tert.-butoxy, trifluoromethyl, Trifluoromethoxy, difluoromethyl, difluoroethyl, pentafluoroethyl, difluoromethoxy, chlorodifluoromethoxy, Chlorotrifluoroethoxy, tetrafluoroethoxy, dichlorodifluoroethoxy, difluorotrichloroethoxy, Hexafluoropropoxy, trifluoromethylthio, difluoromethylthio, chlorodifluoromethylthio, Chlorotrifluoroethylthio, hexafluoropropylthio, methoxymethyl, ethoxymethyl, methylthiomethyl, Ethylthiomethyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl, -n-butoxycarbonyl, i-butoxycarbonyl, sec-butoxycarbonyl, tert. -Butoxycarbonyl, difluoromethylenedioxy, Ethylenedioxy, chlorotrifluoroethylenedioxy, difluoroethylenedioxy, methylenedioxy, trifluoroethylenedioxyl Difluoromethyleneoxydifluoromethyleneoxy, tetrafluoroethylene dioxy, 2-methyl-1,1,2-trifluoroethylene dioxy and / or 2,2-dimethyl-ethyleneoxy is substituted, and / or a pyridin-2-yloxy radical, which in turn, optionally by chlorine, bromine, methyl, trifluoromethyl and / or Trifluoromethoxy is substituted, and / or a pyrimidin-5-yl-oxy radical, which in turn, optionally by methyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, Trifluoromethylthio, chlorine and / or bromine is substituted, R for Hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl or sec-butyl Y stands for oxygen, an S (O) m, CR3R4, CO or NR5 group, in which m stands for 0, 1 or 2, R3, R4 and R5 stand for hydrogen or methyl, n stands for the numbers 0 or 1 and X stands for oxygen or sulfur, where when R is phenyl, R1 is phenyl, R2 is hydrogen and X is Is oxygen or sulfur, in these cases n is the number 1, or if n stands for the number 0, R stands for 4-bromophenyl, R1 stands for 4-chlorophenyl, and R2 stands for hydrogen, in this case X stands for sulfur. 5. Process for the preparation of the new substituted furazans of the formula (Ia) in which R and R¹ are identical or different and represent optionally substituted aromatic or heteroaromatic radicals, R2 represents hydrogen, an OH or COOH group, or optionally substituted radicals from the group consisting of alkyl, alkoxy, cycloalkyl, cycloalkenyl, alkoxycarbonyl, alkoxythiocarbonyl , Alkylsulphonyl, arylsulphonyl or aralkyl, Y stands for oxygen, an S (O), '-CR3R4 -, CO or NR5 group, in which m stands for the numbers 0, 1 or 2, R3, R4 and R5 are the same or are different and stand for hydrogen or alkyl, n stands for the numbers 0 or 1 and X stands for oxygen or sulfur, where when R stands for phenyl, R1 stands for phenyl, R2 stands for hydrogen and X stands for oxygen or sulfur, in these cases n stands for the number 1, or when n stands for the number 0, R stands for 4-bromophenyl, R1 stands for 4-chlorophenyl and R2 stands for hydrogen, in this case X stands for sulfur, characterized in that one a) 3-amino 1,2,5-oxadiazoles of the formula (II) in which Y, R and n have the meanings given above for formula Ia, with iso (thio) cyanates of the formula (III) R1NCX (III) in which R1 and X have the meanings given above for formula Ia, optionally in the presence of catalysts and optionally reacts in the presence of diluents, or b) 3-iso (thio) cyanato-1,2,5-oxadlazole of the formula (IV), in which X, Y, R and n have the meanings given above for formula Ia, with amines of the formula (V), NHR (V) in which R1 and R2 have the meanings given above for formula Ia, optionally in the presence of catalysts and optionally reacted in the presence of diluents. 6. Pesticides, characterized in that they contain at least one substituted furazan of the formula (I) in which R and R1 are identical or different and stand for optionally substituted aromatic or heteroaromatic radicals, R2 for hydrogen, an OH or COOH group or for optionally substituted radicals from the series alkyl, alkoxy, cycloalkyl, cycloalkenyl, alkoxycarbonyl, alkoxythiocarbonyl, Alkylsulfonyl, arylsulfonyl or aralkyl, Y stands for oxygen, an S (O), 'r -CR3R4 -, CO- or -NR5 group, in which m stands for the numbers 0, 1 or 2, R3, R4 and R5 are identical or different and stand for hydrogen or alkyl, n stands for the numbers 0 or 1 and X stands for oxygen or sulfur. 7. Use of compounds of formula (I) according to claim 6 for Control of pests, especially insects and acarids. 8. A method for combating pests, characterized in that that one compounds of the formula (I) according to claim 6 on the pests, preferably Insects and acarids, or their habitat. 9. Process for the manufacture of pesticides, thereby characterized in that compounds of the formula (I) according to Claim 6 with extenders and / or mixed surfactants. 10. Compounds of the formula (IV) in which R stands for an optionally substituted aromatic or heteroaromatic radical, Y stands for oxygen, an S (O) m, CR³R4, CO or 5 WR5 group, in which m stands for the numbers 0, 1 or 2, R³, R4 and R5 are identical or different and stand for hydrogen or alkyl, n stands for the numbers 0 or 1 and X stands for oxygen or sulfur.