MXPA98000761A - 1-fenil-5-anilinotetrazo - Google Patents

Abstract

The present invention relates to the novel 1-phenyl-5-anilinotetrazoles of the formula (I) (See Formula) wherein R 1, R 2, R 3, R 4, m and n have the meanings given in the specification, the processes for their preparation, and its use as microbicides, insecticides and / or herbicides

Description

1 -FENIL-5 -ANILINOTETRAZÓLES DESCRIPTION OF THE INVENTION The present invention relates to the novel 1-phenyl-5-anilinotetrazoles, the processes for their preparation and the use thereof as microbicides, insecticides and / or herbicides. Certain 1-phenyl-4-anilinotetrazoles are described in Collection of Czechoslovak Chemical Communications (1992), 57 (5), 1065-71; Synthetic Communications (1990), 20 (2), 217-26; Synthesis (1987), (9), 823-4; Monatschefte fuer Chemie (1983), 114 (1), 65-70; Journal of Organic Chemistry (1980), 45 (25), 5136-6; ibid. 1977), 42 (23), 3709-13; Journal of Chemical Society, Perkin Transaction 1 (1977), (11), 1241-3; Chem. Zvesti (1979), 33 (4), 521-7; and similar. However, this prior art literature does not describe its uses as agricultural chemicals. The new 1-phenyl-5-anilinotetrazoles of the formula (I) have now been found REF: 26728 wherein R "is hydrogen, halogen, cyano, nitro, alkyl 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms or haloalkylthio of 1 to 4 carbon atoms, R ~ is cyano, nitro, haloalkyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, haloalkyl sulphonyl of 1 to 4 carbon atoms, (alkoxy of 1 to 4 carbon atoms) - carbonyl, aminocarbonyl or inotiocarbonyl, R; is halogen, haloalkyl of 1 to 4 carbon atoms or haloalkoxy of 1 to 4 carbon atoms, R 'is hydrogen, cyano, alkyl of 1 to 4 carbon atoms, (alkyl of 1 to 4 carbon atoms) - carbonyl, (alkoxy of 1 to 4 carbon atoms) - carbonyl, alkylsulfonyl of 1 to 4 carbon atoms , (C 1 -C 4 alkoxy) (C 1 -C 4 alkyl) - carbonyl, phenoxycarbonyl, which may be substituted by nitro or pyridylcarbonyl, which may be substituted by halogen, n is 1, 2 or 3, and when n represents 2 or 3, two or three of R1 may be the same or different, and m is 1 or 2, and when m represents 2, two of R3 may be the same or different. The novel 1- phenyi-5-anilino tetrazoles of the formula (I), according to the invention, can be obtained when a) in the case where R4 is hydrogen the compounds of, the formula (II) R n where R- and n are as defined above, and X is halogen or methylsul fonyl, they are reacted with the compounds of the formula (III) (III wherein R ~, Rs and are as defined above, in the presence of a diluent, and, if appropriate, in the presence of an acidic bonding agent, or b) in the case where R4 is alkyl of 1 to 4 carbon atoms or (alkoxy of 1 to 4 carbon atoms) -carbonyl: the compounds of the formula (IV) (IV) wherein R1, R ~, R ", m and n are as defined above, and R1 is alkyl of 1 to 4 carbon atoms or (C1-C4 alkoxy) -carbonyl, are reacted with sodium azide, in the presence of a diluent, or c) in the case where R 4 is hydrogen: the compounds of the formula (Ib) (Ib) wherein R ", R-, R ', n and m are as defined above, R is alkyl of 1 to 4 carbon atoms or optionally phenyl substituted with nitro, are hydrolyzed in the presence of a diluent, and, if appropriate, in the presence of a base, or d) in the case where R 4 are the radicals co or are defined for R 4 above, with the exception of hydrogen and alkyl of 1 to 4 carbon atoms: The compounds of the formula (Ia) the! wherein R1, R ~, RJ, n and m are as defined above, they are reacted with the compounds of the formula (V) R -Y: v) where R are the radicals as defined for the R "above, with the exception of hydrogen and alkyl of 1 to 4 carbon atoms, and Y is halogen, in the presence of a diluent, and, if appropriate, in the presence of an acid-binding agent, oe) in the case where R 4 is (C 1-4 alkyl) -carbonyl or (C 1-4 alkoxy) - (C 1-4 alkyl) -carbonyl: the above-mentioned compounds of the formula ) are reacted with the compounds of the formula (VI) : v? where R; it is alkyl of 1 to 4 carbon atoms or (alkoxy of 1 to 4 carbon atoms) - (alkyl of 1 to 4 carbon aromos), optionally in the presence of a diluent and in the presence of an acid catalyst.

The 1-phenyl-5-anilinotetrazoles of the formula (I) according to the invention show insecticidal action and / or fungicidal action and / or herbicidal action. Surprisingly, the l-phenyl-5-anilinotetrazoles of the formula (I) according to the invention have a high insecticidal activity, fungicidal activity and / or herbicidal activity. In this specification, the halogen in the terms "halogen", "haloalkyl" and "haloalkoxy" represents fluorine, chlorine, bromine or iodine, preferably is fluorine, chlorine or bro. The "alkyl" may be straight or branched chain and includes, for example, methyl, ethyl, propyl, isopropyl, n-, iso-, sec- or tert-butyl, and the like. The "alkoxy" may be straight or branched chain and includes, for example, methoxy, ethoxy, propoxy, isopropoxy, n-, iso-, sec- or tert-butoxy, and the like.

The "haloalkyl" can be straight or branched chain and includes, for example, trifluoromethyl, 2, 2, 2-trifluoroethyl, chloroethyl, and the like. The "haloalkoxy" may be straight or branched chain and includes, for example, trifluoromethoxy, 2,2,2-trifluoroethoxy, and the like. The "haloalkylthio" can be straight or branched chain and includes, for example, trifluoro ethylthio, 2,2,2-trifluoroethylthio, and the like. The "alkylsulfonyl" may be straight or branched chain and includes, for example, methylsulfonyl, ethylsul fonyl, propylsulfonyl, isopropylsulfonyl, and the like. The "haloalkylsulfonyl" may be straight or branched chain and includes, for example, t-fluoromethyl sulphonyl, 2,2,2-trifimethyl-ethyl-fonyl, and the like. Among the 1-phenyl-5-anilinotetrazoles of the formula (I), the preferred compounds are those in which R "is hydrogen, halogen, cyano, nitro, alkyl of 1 to 3 carbon atoms, fluoroalkyl of 1 to 3 atoms of carbon, fluoroalkoxy of 1 to 3 carbon atoms or fluoroalkylthio of 1 to 3 carbon atoms, R "is cyano, nitro, haloalkyl of 1 to 3 carbon atoms, alkylsulfonyl of 1 to 3 carbon atoms, haloalkylsul fonyl of 1 to 3 carbon atoms, (alkoxy of 1 to 3 carbon atom) - carbonyl, aminocarbonyl or aminothiocarbonyl. R; is halogen, fluoroalkyl of 1 to 3 carbon atoms, fluoroalkoxy of 1 to 3 carbon atoms, R 4 is hydrogen, cyano, alkyl of 1 to 3 carbon atoms, (alkyl of 1 to 3 carbon atoms) - carbonyl, (alkoxy of 1 to 3 carbon atoms) - carbonyl, alkylsulfonyl of 1 to 3 carbon atoms, (alkoxy of 1 to 2 carbon atoms) - (alkyl of 1 to 2 carbon atoms) -carbonyl, phenoxycarbonyl optionally nitro- substituted or optionally chloro-substituted pyridylcarbonium, n is 1 or 2, and when n represents 2, two of R may be the same or different, and m is 1 or 2, and when m represents 2, two of R ~ may be the same or different . The very particularly preferred 1-phenyl-5-anilinotetrazoles of the formula (I) are those wherein: R - 'is hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, trifluoromethyl, trifluoroethoxy or trifluoromethyl thio, R "is cyano, nitro, trifluoromethyl, methylsulfonyl, ethylsul fonyl, trifluoromethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, aminocarbonyl or aminothiocarboni R "is fluorine, chlorine, bromine, trifluoromethyl or trifluoromethoxy. R '! it is hydrogen, cyano, methyl, methylcarbonyl ,. methoxycarbonyl, ethoxycarbonyl, methylsulfonyl, methoxymethylcarbonyl, phenoxycarbonyl, 4-nitrophenoxycarbonyl or 2,6-dichloro-4-pyridylcarbonyl, n is 1 or 2, and when n represents 2, two of R1 may be the same or different, and m is 1 or 2, when m represents 2, two of RJ can be the same or different.

Specific examples of the l-phenyl-5-anilino tetrazoles of the formula (I) according to the invention, which may be mentioned, are the compounds shown in Table 1 described below.

In the aforementioned process (a), for example, if 5-chloro-1-phenyltetrazole and 4-amino-3-trifluoro-cetylbenzonitrile are used as starting materials, the course of the reaction can be represented by the following equation: In the above-mentioned process (b), for example, if N '- (4-fluoro-phenyl) -N- (4-cyano-2,5-di-fluoro-phenyl) -N-methyl-1-c is used As for amidine and sodium azide as initial materials, the course of the reaction can be represented by the following equation: In the aforementioned process (c), if hydrolysis is, for example, l- (4-trifluoromethylphenyl) -5- (2-chloro-4-trifluoromethyl-N-methoxycarbonyl-anilino) tetrazole, the course of the reaction may be to be represented by the following equation: In the above-mentioned process (-d), if for example l- (4-trifluoromethyl-phenyl) -5- (4-cyano-2,5-difluoroaniiino) tetrazole and methanesulfonyl chloride are used as starting materials, the The course of the reaction can be represented by the following equation: In the above-mentioned process (e), if for example l- (4-trifluoromethoxyphenyl) -5- (4-cyano-2, 5-difluoroanilino) -tetrazole and acetic anhydride are used as starting materials, the course of The reaction can be represented by the following equation: N = N In process (a), the starting materials of formula (II) mean the compounds based on the above definition of R1, n and X, preferably substituents based on the above-preferred definitions of R1 and n, and X preferably represents chlorine or bromine. The compounds of the formula (II) used as starting materials include: 5-chloro-1-phenyltetrazole, 5-chloro-1- (4-chloro-phenyl) tetrazole, 5-chloro-1- (4-chlorophenyl) tetrazole, -chloro-l- (4-bromo-phenyl-1) tetrazole, 5-chloro-l- (4-trifluoromethyl-phenyl) -tetrazole, 5-chloro-l- (4-trifluoromethoxy-l-phenyl) -tetrazole, 5-chloro-l- (3 -chloro-4- trifluoromet i Ifenil) tetrazole, 5-met i lsul fonyl-1- (3-fluorophenyl) tetrazole, and illars. The compounds of the formula (II) are described, as well as the processes of their preparation, in the Japanese Patent Publication Kokai Sho No. 56-86175, the German Patent DE-A-1251327 and the British Patent GB-A-1128025 , or they can be synthesized in a similar way to those described in these references.

In the process (a) of the present invention, the starting materials of the formula (III) mean the compounds based on the above definitions of Rz, R1 and m, preferably substituents based on the above preferred definitions of Rd RJ and m. The compounds of the formula (III) used as starting material are well known in the field of organic chemistry and examples thereof include, for example, 4-amino-3-trifluoromethyl-3-benzonyl, 4-amino-2, 5 -di fluo obenzoni trilo, 2-chloro-4-trifluorornethyl-añil ina, 2-chloro-4-tri fluoromet i lsul fonilanilina, 2-chloro-4-metilsulfonilanilina, and the like. In the process (b) according to the invention, the starting materials of the formula (IV) mean the compounds based on R1, R ~, R ~, m, n and R ", preferably substituents based on the above preferred definitions of R1 , R ~, R m, and R: 'preferably represent alkyl of 1 to 3 carbon atoms or (C 1 -C 3 alkoxy) -carbonyl.

In process (b), examples of the compounds of formula (IV) used as starting material include: N '- (4-fluorophenyl) -N- (4-cyano-2,5-difluorophenyl) -N-methylchloroformamidine , N '- (4-trifluoromethyl-phenyl) -N- (4-cyano-2,5-difluorophenyl) -N-methylchloro-formamidine, N' - (4-trifluoromethyl-phenyl) -N- (2-chloro-4-) trifluoromethylphenyl) -N-methyl-chloroformamidine, and the like. The compounds of the formula (IV) can be produced, for example, by the processes described in the Journal of Organic Chemistry, (1977), 42 (23), 3709-3713 and the like, and can be synthesized, for example, by the next method.

The compounds of the formula (VII (VII where R ~ and n are as defined above, they are reacted with the compounds of the formula X (viir wherein R :, R ?, m and R5 are as defined above, in the presence of a diluent, and, if appropriate, in the presence of an acid-binding agent. The compounds of the formula (VII) and (VIII) are compounds well known in the field of organic chemistry. In the process (c) according to the invention, the starting materials of the formula (Ib) mean the compounds based on the above definitions of R1, R ~, R ', R ", m and n, preferably substituents based on the definitions Preferred priors of R ~, R ~ ', R', m and R, and R "preferably represents alkyl of 1 to 3 carbon atoms, phenyl or 4-nitrophenyl The compounds of the formula (Ib) used as the starting material are the compounds according to the invention, which can be synthesized by process (b) above.Specific examples thereof include: 1- (4-fluorophenyl) -5- (2-chloro-4-trifluoromethyl-N -methoxycarboni lamini flax) tetrazole, 1- (4-trifluoromethylphenyl) -5- (2-chloro-4-t-fluoromorph-1-N-metoxicarbonyl-anilino) tetrazole, 1- (4-trifluoromethyl-toxin 1) -5- (2-chloro-4-tri-fluoromethyl-N-methoxycarbonyl-anilino) tetrazole and the like. In the processes (d) and (e) according to the invention, the starting materials of the formula (la) mean the compounds based on the definitions of R1, R ", R ', myn, preferably substituents based on the preferred definitions The compounds of the formula (Ia) used as initial material are compounds according to the invention, which can be synthesized by the above processes (a) or (c).

Specific examples of the compounds of the formula (la) include: 1- (4-trifluoromethyl-phenyl) -5- (4-cyano-2,5-difluoromethylanilino) tetrazole, 1- (4-trifluoromethoxy phenyl) - 5- (4-cyano-2, 5-difluoromethylanilino) tetrazole, and the like.

In the processes (d) according to the invention, the starting materials of the formula (V) mean the compounds based on the above definitions of R and Y, R 'preferably represents cyano, (alkyl of 1 to 3 carbon atoms) -carbonyl, (C1-C3-alkoxy) -carbonyl, alkylsulfonyl of 1 to 3 carbon atoms, phenoxycarbonyl which may be substituted with nitro, or pyridylcarbonyl which may be substituted with chloro. And it preferably represents chlorine or bromine. The compounds of formula (V) used as starting materials are well known in the field of organic chemistry, and examples thereof include acetyl chloride, propionyl chloride, methoxyacetyl chloride, methyl chloroformate, ethyl chloroformate, cyanogen bromide, methanesulfonyl chloride, and the like.

In the process (e) according to the invention, the starting materials of the formula (VI) mean the compounds based on the above definitions of Rr, which preferably represents alkyl of 1 to 3 carbon atoms or (alkoxy of 1 to 2) carbon atoms) - (alkyl of 1 to 2 carbon atoms). The compounds of the formula (VI) used as the starting material are well known in the field of organic chemistry and examples thereof include acetic anhydride. The reaction of the above process (a) can be carried out in an appropriate diluent. Examples of suitable diluents are aliphatic, alicyclic or aromatic hydrocarbons (which may be optionally chlorinated) such as pentane, hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1 / 2-dichloroethane, chlorobenzene and dichlorobenzene; ethers such as diethyl ether, methyl ethyl ether, diisopropyl ether, dibutyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF) and diethylene glycol dimethyl ether (DGM); ketones such as acetone, me ti 1-et i 1 -ketone (MEK), methyl-isopropyl-ketone and methyl-isobutyl ketone (MIBK), nitriles such as acetonitrile, propionitrile and acrylonitrile; esters such as ethyl acetate and amyl acetate; acid amides such as dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone and hexamethylphosphoric triamide (HMPA); sulfones and sulfoxides such as dimethyl sulfoxide (DMSO) and sulfolane; etc. The reaction of process (a) can be carried out in the presence of an acid coupling agent. Examples of suitable acid coupling agents are inorganic bases, for example, hydroxides, carbonates and bicarbonates of alkali metals or alkaline earth metals and alkoxides such as sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, lithium hydroxide. , sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium tert-butoxide and potassium tert-butoxide; inorganic alkali metal amides, such as lithium amide, sodium amide and potassium amide; organic bases, for example, alcoholates, tertiary amines, dialkylaminoani 1 -asas and pyridines, such as t-ethylamine, 1, 1, 4, 4- and rametilet-lendiamine (TMEDA), N, N-dimethylaniline, N, N-diethylaniline, pyridine, 4-dimethylaminopyridine (DMAP), 1,4-diazabicyclo [2, 2, 2] octane (DABCO) and 1,8-diazabicyclo [5,, 0] undec-7-ene (BOD), organic lithium compounds , such as ethyl lithium, n-butyllithium, sec-butyllithium, tert-butyllithium, phenyllithium, dimethyl-copper-lithium, lithium diisopropylamide, lithium cyclohexyl isopropylamide, lithium dicycloexylamide, n-butyl- lithium-DABCO, n-butyl-lithium-DBU and n-butyl-lithium-TMEDA. The reaction of process (a) can be conducted at a temperature within a substantially wide range, but it is generally possible to employ a reaction temperature of about -20 to about 100 ° C, preferably about -5 to about 80 ° C. . In addition, the reaction should preferably be conducted under normal pressure, but this may optionally be operated under elevated or reduced pressure. To carry out process (a) for example, one mole of the compound of the formula (II) can be reacted with 1 to 1.1 molar amounts of the compound of the formula (III) in a diluent such as tetrahydrofuran, in the presence of an acid binding agent, to thereby obtain the desired compound. The reaction of the above process (b) can be carried out in an appropriate diluent. Examples of suitable diluents are water; aliphatic, alicyclic or aromatic hydrocarbons(which may optionally be chlorinated) such as pentane, hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene and dichlorobenzene; ethers such as ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF), and diethylene glycol dimethyl ether (DGM); ketones such as acetone, methyl ethyl ketone (MEK), methyl isopropyl ketone and methylisobutyl ketone (MIBK); nitriles such as acetonitrile, propionitrile and acrylonitrile; alcohols such as methanol, ethanol, isopropanol, butanol and ethylene glycol; esters such as ethyl acetate and amyl acetate; acid amides such as dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone and hexamethylphosphoric triamide (HMPA); sulfones and sulfoxides such as dimethyl sulfoxide (DMSO) and sulfolane; etc . The reaction of process (b) can be conducted at a temperature within a substantially wide range, but it is generally possible to employ a reaction temperature of from about 0 to about 120 ° C, preferably about 20 to about 100 ° C. In addition, the reaction should preferably be conducted under normal reaction, but this may optionally be operated under elevated or reduced pressure. To carry out process (b), for example, 1 mole of the compound of the formula (IV) can be reacted with 1 to 1.5 molar amounts of sodium azide in a diluent such as a mixed solvent of acetone and water, to obtain with this the desired compound. The reaction of process (c) above can be carried out in an appropriate diluent. Preferred examples of suitable diluents are water or alcohols such as methanol, ethanol, isopropanol, butanol and ethylene glycol. However, other diluents may also be used and examples thereof are aliphatic, alicyclic or aromatic hydrocarbons (which may be optionally chlorinated) such as pentane, hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene and dichlorobenzene; ethers such as diethyl ether, methyl ethyl ether, diisopropyl ether, dibutyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF) and diethylene glycol dimethyl ether (DGM); ketones such as acetone, methyl-ethyl ketone (MEK), methyl-isopropyl ketone and methyl-isobutyl-ketone (MIBK); nitriles such as acetonitrile, propionitrile and acrylonitrile; esters such as ethyl acetate and amyl acetate; acid amides such as dimethylformamide (DMF), dimethylacetamide (DMA), N-met i Ipyrrolidone, 1,3-dimethyl-2-imidazolidinone and triamide hexamethyl phosphoric acid (HMPA); sulfones and sulfoxides such as dimethyl sulfoxide (DMSO) and sulfolane; etc. The reaction of process (c) can be carried out preferably in the presence of an inorganic base. Examples of inorganic bases are hydroxides, carbonates and bicarbonates of alkali metals and alkaline earth metals, such as sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide. The reaction of process (c) can be conducted at a temperature within a substantially wide range, but it is generally possible to employ a reaction temperature of from about 0 to about 150 ° C, preferably about 20 to about 100 ° C. In addition, the reaction should preferably be conducted under normal pressure, but this may optionally be operated under elevated or reduced pressure. To carry out process (c), for example, 1 mole of the compound of the formula (Ib) can be reacted with 1 to 3 molar amounts of a base in a diluent such as methanol, to obtain with this the desired compound. The reaction of process (d) above can be carried out in an appropriate diluent. Examples of suitable diluents are aliphatic, alicyclic or aromatic hydrocarbons (which may be optionally chlorinated) such as pentane, hexane, cyclohexane, petroleum ether, iigroin, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane, chlorobenzene and dichlorobenzene; ethers such as diethyl ether, methyl ethyl ether, diisopropyl ether, dibutyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF) and diethylene glycol dimethyl ether (DGM); ketones such as acetone, methyl ethyl ketone (MEK), methyl isopropyl ketone and methyl isobutyl ketone (MIBK); nitriles such as acetonitrile, propionitrile and acrylonitrile; esters such as ethyl acetate and amyl acetate; acid amides such as dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone and tria-ida hexamethylphosphoric acid (HMPA); sulfones and suiphoxides such as dimethyl sulfoxide (DMSO) and sulfolane; etc. The reaction of process (d) can be carried out in the presence of an acid-binding agent. Examples of suitable acid binding agents are inorganic bases, for example, hydroxides, carbonates and bicarbonates of alkali metals or alkaline earth metals, such as sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate, hydroxide lithium, sodium hydroxide, potassium hydroxide and calcium hydroxide; inorganic alkali metal amides, such as lithium amide, sodium amide and potassium amide; metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride; organic bases, for example alkoxides, tertiary amines, dialkylaminoanilines and pyridines, such as sodium tert-butoxide, potassium tert-butoxide, triethylamine, 1,1,4,4-tetramethylethylenediamine (TMEDA), N, N-dimethylaniline, N , N-diet ilaniline, pyridine, 4-dimeti laminopyridine (DxMAP), 1,4-diazabicyclo [2.2, 2] octane (DABCO) and 1,8-diazabicyclo [5, 4, 0] undec-7-ene (DBU); organic lithium compounds, such as methyl lithium, n-butyllithium, sec-butyllithium, t-butyl-lithium, phenyllithium, dimethyl-copper-lithium, lithium diisopropylamide, lithium cyclohexyl isopropylamide, dicyclohexylamide lithium, n-butyl-lithium-DABCO, n-butyl-lithium-DBU and n-butyl-lithium-TMEDA. The reaction of process (d) can be conducted at a temperature within a substantially wide range, but it is generally possible to employ a reaction temperature of from about 0 to about 120 ° C, preferably from about 10 to about 100 ° C. In addition, the reaction should preferably be conducted under normal pressure, but this may optionally be operated under elevated or reduced pressure. To carry out process (d), for example, 1 mole of the compound of the formula (la) can be reacted with 1 a, 1.5 molar amounts of the compound of the formula (V) in a diluent such as tetrahydrofuran, in presence of an acid binding agent to obtain the target compound therewith. The reaction of process (e) above can be carried out without a diluent or in an appropriate diluent. Examples of suitable diluents are aliphatic, alicyclic or aromatic hydrocarbons (which may be optionally chlorinated) such as pentane, hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane, chlorobenzene and dichlorobenzene; ethers such as ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF) and diethylene glycol dimethyl ether (DGM); ketones such as acetone, methyl-et-il-ketone (MEK), methyl-isopropyl-ketone and met-il-isobutyl-ketone (MIBK); nitriles such as acetonitrile, propionitrile and acrylonitrile; alcohols such as methanol, ethanol, isepropane, butanol and ethylene glycol; esters such as ethyl acetate and amyl acetate; acid amides such as dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone, 1,3-diethyl-2-imidazolidinone and triamide hexamethyl phosphoric acid (HMPA); sulfones and sulfoxides such as dimethyl sulfoxide (DMSO) and sulfolane; etc. The reaction of the process (e) can be carried out in the presence of an acid catalyst. Examples of suitable acid catalysts are mineral acids such hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid, sodium acid sulfite; organic acids such as formic acid, acetic acid, trifluoroacetic acid, propionic acid, methansulfonic acid, benzenesulfonic acid, p-toluensulonic acid; organic salts of hydrochloric acid amines such as the pyridine-hydrochloric acid salt, tr-ylamine-hydrochloric acid salt; etc. The reaction of process (e) can be conducted at a temperature within a substantially wide range, but it is generally possible to employ a reaction temperature of from about 0 to about 150 ° C, preferably from about 20 to about 120 ° C. In addition, the reaction should preferably be conducted under normal pressure, but this may optionally be operated under elevated or reduced pressure. To carry out the process (e), for example, an excessive amount of the compound of the formula (VI), which can also act as a solvent, can be reacted with the compound of the formula (la) in the presence of an acid catalyst to obtain the desired compound therewith. The 1-phene-1-5-inotetrazole of the formula (I) according to the invention show powerful microbicidal action, insecticidal action and / or herbicidal action. In addition, the l-phenyl-5-anilinotetrazoles of the formula (I) according to the invention do not show phytotoxicity against cultivated plants. In this way, they can be used as microbicides, insecticides and / or herbicides. The 1-phenyl-5-anilinotetrazoles of the formula (I) according to the invention show a powerful microbicidal action, and can be used in practice to combat unwanted microorganisms. The 1-phenyl-5-anilinotetrazole of the formula (I) are suitable for use as plant protection agents. Fungicidal agents in the protection of plants are used to combat Plasmodioforomycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Asco icetos, Basidiomycetes and Deuteromycetes. Bactericidal agents are used in plant protection to combat Pseudomonoadaceae, Rhixobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae. Some causative organisms of fungal and mycotic diseases included under the aforementioned headings are mentioned below as non-limiting agents: the Xanthomonas species, such as, for example, Xanthomonas campestris pv. oryzae; the Pseudomonas species, such as, for example, Pseudomonas syringae pv. lachrymans; the Erwinia species, such as, for example, Erwinia amylovora; Pythium species, such as, for example, Pythium ultimum; the Phytophtora species, such as, for example, Phytophtora infestants; the species Pseudoperonospora, such as, for example, Pseudoperonospora cubensis; the Plasmopara species, such as, for example, Plasmopara viticola; the Peronospora species, such as, for example, Peronospora pisior pv. brassicae; the Erysiphe species, such as, for example, Erysiphe graminis; the species Sphaerotheca, such as, for example, Sphaerotheca fuliginea; the Podosphaera species, such as, for example, Podosphaera leucotricha; the Venturia species, such as, for example, Venturia inaequalis; Pyrenophora species, such as, for example, Pyrenophora teresor pv. grass; (conical shape: Drechslera, Synonym: Helminthosporium); the species Cochliobolus, such as, for example, Cochliobolus sativus; the Uromyces species, such as, for example, Uromyces appendiculatus; the species Puccinia, such as, for example, Uromyces appendiculatus; the species Puccinia, such as, for example, Puccinia recondita; the Tiletia species, such as, for example, Tilletia caries; the Ustilago species, such as, for example, Ustilago nudaor, Ustilago avenae; the species Pellicularía, such as, for example, Pellicularia sasakii; the species Pyricularia, such as, for example, Pyricularia oryzae; the Fusarium species, such as, for example, Fusarium culmoru; the species Botryti s, such as, for example, Botryzis cinerea; the species Septoria, such as, for example, Septoria nodorum; the species Leptosphaeria, tai as, for example, Leptosphaeria nodorum; the Cercospora species, such as, for example, Cercospora canescens; the species Alternarla, such as, for example, Alternarla brassicae; the species Pseudocercosporella, such as, for example, Pseudo fence sporella herpotrichoides. The good tolerance, by the plants, of the 1-phenyl-5-anilinot etrazoles of the formula (I), at the concentrations required to combat plant diseases, allows the treatment of the parts of the plants above the ground , of the vegetative propagation material and the seeds, and of the soil. The 1-phenyl-5-anilinotetrazoles of the formula (I) have a favorable level of toxicity for warm-blooded animals, and can be used to combat arthropod pests especially insects, which are found in agriculture, in reforestation , in the protection of stored products and materials, and in the field of hygiene. These are active against the normally sensitive and resistant species, and against all or some stages of development.

The aforementioned pests include: from the Isopoda class, for example, Oniscus Asellus, Armad i.l I? Dium vulgaraand and Porcellio saa ± > er; from the class of the Diplopoda, for example, Blaniulus gut tul a tus; of the Chilopoda class, for example, Geophilus carpophagus, and Scutigera spec.; from the class of the Symphyla, for example, Scutigerella immacul ta; of the order of the Thysanura, for example, Lepisma saccharina; of the order of the Collembola, for example, Onychiurus arma tus; of the order of the Orthoptera, for example, Blatta orientali s, Periplaneta americana, Leucophaea maderae, Germanic Blattella, Acheta domesticus r Gryllotalpa spp. , Locusta migratoria, migratorioides r Melanoplus differentialis and Schistocerca gregaria; of the order of the Dermápteros, for example, Auricular Fungi; of the order of the Isoptera, for example, Reticulitermes spp.; of the order of the Anoplura, for example, Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haeraatopinus spp. , and Linognathus spp.; of the order of the Mallophaga, for example, Trichodectes spp. and Damalinea spp.; of the order of the Thysanoptera, for example, Hercinothrips femoralis and Thrips tabaci; of the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma guadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp .; from the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporarioru, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotetix cincticeps, Lecanium ate, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudoccccus spp., and Psylla spp .; of the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hiponomeuta padella, Plutella macullipennis, Malacosoma neustria, Euproctis chysorrhea, Lymantria spp. , Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mames r brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia podana, Capua reticulana, Choristoneura fu iferana, Clysia ambiguella, Homona magnánima and Tortrix viridana; of the order of the Coleoptera, for example, Anobium punctatum, Rhyzopertha dominica, Acanthoscelides obtectus, Acanthoscelides obtectus, Hylotrupes baj lus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes cnrysocephala, 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., Ccnoderus spp., Melolontha melolontha, Amphimallon solstitialis and Costelytra zealandica; from the order of Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaoinis and Vespa spp .; from the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chyrsomya spp., Cuterebra spp., Gastrophilus spp. , Hyppobosca spp., Stomoxys spp., Cestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomya hyoscyami, Ceratitis capitata, Dacus oleae and Typula paludosa. Some of the 1-phenyl-5-anilinotetrazoles of the formula (I) according to the invention can be used as defoliators, desiccants, agents for destroying broadleaf plants and, especially, as weed removers. By weeds, in the broadest sense, we mean all the plants that develop in the places where they are not desired. If the substances according to the invention act as total or selective herbicides, they depend essentially on the amount used.

The active compounds according to the invention can be used, for example, in relation to the following plants: Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chemopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon ,. Emex, Datura, Viola, Galeopsis, Papaver and Centaurea. Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linu, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita. Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Oats, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum , Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera. Cultures of Monocotiledóneas of the sorts: Oryza, Zea, Triticum, Hordeum, Oats, Sécale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and All ium. However, the use of the l-phenyl-5-anilinotetrazoles of the formula (I) according to the invention is in no way restricted to these genera, but also extends in the same way to other plants. The 1-phenyl-5-anilinotetrazoles of the formula (I) are suitable, depending on the concentration, for the total control of the weeds, for example, in the industrial land and on railway tracks, and on the tracks and land with or without tree planting. Likewise, the l-phenyl-5-anilino tet rats of the formula (I) can be used to fight weeds in perennial crops, for example, in reforestations, decorative tree plantations, orchards, vineyards, citrus orchards, orchards. nuts, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantations and hop fields, and for selective weed control in annual crops. The 1-phenyl-5-ani-lyotetrazoles of the formula (I) can be converted to customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, foams, pastes, granules, tablets, aerosols, synthetic and natural materials impregnated with the active compound, very thin capsules in polymeric substances, coating compositions for use on the seeds, and formulations used with the ignition equipment, such as fumigation cartridges, fumigation cans and fumigation coils, as well as cold fog of ULV and hot mist formulations. These formulations can be produced in a known manner, for example, by mixing the 1-phenyl-5-anilino tetrazoles of the formula (I) with extenders, i.e. liquid or gaseous liquified diluents or carriers, or solids, optionally with the use of surface active agents, ie, emulsifying agents and / or dispersing agents and / or foaming agents. In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. Suitable diluents or liquid solvent carriers are aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, chlorinated aliphatic hydrocarbons or chlorinated aromatics, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins. , for example mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, as well as water. By diluents or liquefied gaseous carriers, means liquids that could be gaseous at normal temperature and under normal pressure, for example, aerosol propellants, such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide. As solid carriers that can be used there are crushed natural minerals, such as kaolins, clays, talc, chalk, quartz, atapulguite, montmorillonite or diatomaceous earth, and crushed synthetic minerals, such as highly disperse silicic acid, alumina and silicates. As solid carriers for granules, natural ground and fractionated rocks such as calcite, marble, pumice, sepiolite and dolomite can be used, as well as synthetic granules of inorganic and organic foods, and granules of organic material such as sawdust, coconut shells, cobs of corn and tobacco stalks. As emulsifying and / or foaming agents, nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkyl aryl polyglycol ethers, alkyl sulfonates, can be used. alkyl sulfates, aryl sulfonates as well as albumin hydrolysis products. Dispersing agents include, for example, waste liquor of lignin sulfite and mecellulose. Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or networks, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulation. It is possible to use dyes such as inorganic pigments, for example iron oxide, titanium oxide and Prussian blue, and organic pigments such as alizarin pigments, azo pigments or metallic phthalocyanine pigments, and trace nutrients, such as iron salts , manganese, boron, copper, cobalt, molybdenum and zinc. The formulations in general contain 0. 1 to 95 weight percent of the active compound, preferably 0.5 to 90 weight percent. The 1-phenyl-5-anilinotetrazoles of the formula (I) according to the invention can be present in their commercially available formulations, and in the forms of use prepared with these formulations, as a mixture with other active compounds, such as insecticides, attractants, sterilizers, acaricides, nematicides, fungicides, regulatory substances, growth or herbicides. Mixable insecticides include, for example, organic phosphate, carbamates, carboxylates, chlorinated hydrocarbons and insecticidal substances produced by microorganisms. When the 1-phenyl-5-anilinotetrazoles of the formula (I) are mixed with herbicides, the following known herbicides can be exemplified. for the control of weeds in cereal crops, 4-amino-6- (1,1-dimethylethyl) -3-ethylthio-l, 2,4-triazin-5 (4H) -one, 1-amino-6-ethylthio -3- (2,2-dimethyl thiolpropyl) -l, 3,5-triazin-2,4 (lH, 3H) -dione, N- (2-benzothiazolyl) -N, N'-dimethylurea, etc. for the control of weeds in the cultivation of Saccharum officinarum: 4-amino-3-methyl-1-6-phene 1-1, 2,4-triazine-5 (4H) -one, etc. for the control of weeds in the Glycine culture: 4-amino-6- (1,1-dimethylethyl) -3-methylthio-1,2,4-riazin-5 (4H) -one, etc.

The 1-phenyl-5-anilinotetrazoles of the formula (I) according to the invention can also be present as a mixture with synergists. Synergistic agents are compounds that increase the action of the active compounds, without it being necessary for the added synergistic agent to be active on its own. The content of the l-phenyl-5-anilino tetrazoles of the formula (I) according to the invention in its commercially available form of use can be varied within wide limits, for example within the range of 0.0000001 to 100% in weight, preferably between 0.00001 and 1% by weight. The 1-phenyl-5-anilinotetrazoles of the formula (I) according to the invention can be used against pests, in a manner customary for the forms of use. To combat hygiene pests and stored grain pests, the 1-phenyl-5-anilinotetrazoles of the formula (I) according to the invention are extremely excellent in alkali stability on limestone substances and in the residual action on wood and soil. When the 1- phenyl-5-anilino tet rats of the formula (I) according to the invention are used as herbicides, they can be applied at any stage of pre-emergence or post-emergence of the plants. Also, these can be incorporated into the soil before planting. The amount of application of the l-phenyl-5-anilinotetrazoles of the formula (I) can be varied within a substantial range, and varies basically depending on the desired properties of the effect. But when the l-phenyl-5-anyl inotetrazoles of the formula (I) are used as herbicides, the amount of application as the 1-phenyl-5-anilinotetrazoles of the formula (I) can be exemplified, for example, by approximately 0.001 kg / ha up to approximately 5 kg / ha, preferably from approximately 0.1 kg / ha up to approximately 2 kg / ha. Thus, the following Examples illustrate the invention, but these should not be considered as limiting the scope of the invention.

Synthesis Example 1 4-Amino-3-trifluoromethyl-benzonitrile (0.9 g) was added to a solution of tetrahydrofuran (25 ml) of sodium hydride (0.5 g, 60% in oil) at room temperature. The mixture is stirred at room temperature for approximately 10 minutes until the generation of hydrogen gas ceased. Subsequently, 5-chloro-l-phenyltetrazole (0.9 g) was added thereto and the mixture was stirred for 2 hours. The reaction solution was drained in 100 ml of ice water and the organic layer was distilled under reduced pressure. Activated carbon was added to the aqueous layer and the aqueous layer was filtered. Subsequently, the pH of the filtrate was adjusted to 2 -3 with concentrated hydrochloric acid. The precipitated crystals were cast by filtration and washed with water and n-hexane to obtain l-phenyl-5- (4-cyano-2-trifluoromethylanilino) -tetrazole (1.5 g). Melting point: 154-156 ° C Synthesis Example 2 4-Methylamino-2,5-difluorobenzonitrile was added to a solution of tetrahydrofuran (25 ml) of sodium hydride (0.4 g, 60% in oil). Until the generation of hydrogen gas ceased, stirring was continued while remaining at 0 to 5 ° C for about 10 minutes. Subsequently, 4-fluorophenyl-isocyanide dichloride was added thereto and stirring was continued at room temperature for 3 hours. After activated carbon was added to the reaction solution, the solution was filtered and the filtrate was distilled under reduced pressure. Subsequently, the resulting residue was dissolved in acetone (30 ml). An aqueous solution (6 ml) of sodium azide (0.6 g) was added thereto and the mixture was heated under reflux for 3 hours. After the completion of the reaction, water (80 ml) was added thereto and then the organic solvent was distilled under reduced pressure. The precipitated crystals were collected by filtration and washed with water and in n-hexane to obtain 1- (4-fluorophenyl) -5- (4-cyano-2,5-difluoro-N-met il-anilino) tetrazole (2.3 g). Melting point: 162.5 ° C Synthesis Example 3 Methyl-N- (2-chloro-4-trifluoromethylphenyl) carbamate (2.0 g) was added to a solution of tetrahydrofuran (25 ml) of sodium hydride (0.4 g, 60% in oil) at 0 to 5 ° C. Until the generation of hydrogen ceased, stirring was continued while remaining at 0-5 ° C for about 10 minutes. Subsequently, 4-trifluoromethylphenyl-isocyanide dichloride (1.9 g) was added thereto and stirring was continued at room temperature for 3 hours. Activated carbon was added to the reaction solution, the solution was filtered and then the filtrate was distilled under reduced pressure. The resulting residue was dissolved in acetone (30 ml). An aqueous solution (7 ml) of sodium azide (0.65 g) was added thereto and the mixture was heated under reflux for 3 hours. After completion of the reaction, water (80 ml) was added thereto, and extracted with dichloromethane. After drying over anhydrous sodium sulfate, dichloromethane was distilled off under reduced pressure. The resulting residue was dissolved in ethanol (15 ml) and then hexane (30 ml) was added thereto. The precipitated crystals were collected by filtration and washed with a mixed solution of ethanol: hexane (1: 2) to obtain l- (4-trif luoromethylphenyl) -5- (2-chloro-4-trifluoromethyl-N-ethoxycarbonyl-anilino) tetrazole (1.8 g). Melting point: 111-112 ° C Synthesis Example 4 A mixed solution of l- (4-trifluoromethylphenyl) -5- (2-chloro-4-trifluoromethyl-N-methoxycarbonyl-anilino) tetrazole (1.2 g), methanol (15 ml) and potassium hydroxide ( 0.4 g) was stirred at room temperature for 3 hours. After completion of the reaction, hydrochloric acid (5%, 80 ml) was added thereto. The precipitated crystals were collected by filtration and washed with water to obtain 1- (4-trifluoromethyl-phenyl) -5- (2-chloro-4-trifluoromethylanilino) tetrazole (1.0 g). Melting point: 115.5-116.5 ° C.

Example of Synthesis 5 1- (4-trifluoromethylphenyl) -5- (4-cyano-2,5-difluorophenylamino) tetrazole (1.5 g) was added to a solution of tetrahydrofuran (25 ml) of sodium hydride (0.2 g, 60% in oil) at room temperature. Stirring was continued at room temperature for approximately 5 minutes until the generation of hydrogen gas ceased. Subsequently, methanesulfonyl chloride (0.5 g) was added thereto and stirring was continued at room temperature for approximately 24 hours. After completion of the reaction, the solvent was distilled under reduced pressure. Water was added to the resulting residue, which was extracted twice with ethyl acetate. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was dissolved in hot ethanol. After cooling, the precipitated crystals were collected by filtration and washed successively with cold ethanol and n-hexane to obtain 1- (4-trifluoromethylphenyl) -5- (4-cyano-2,5-difluoro-N-methylsul fonil-anilino) -tetrazole (1 g). Melting point: 129.5-130.5 ° C Synthesis Example 6 A mixed solution of acetic anhydride (15 ml), 1- (4-trifluoromethoxy phenyl) -5- (4-cyano-2,5-difluoroanilino) tetrazole (1.5 g) and concentrated sulfuric acid (1 ml) was stirred at 70 -80 ° C for 1 hour. Subsequently, the unreacted acetic anhydride was distilled under reduced pressure, the residue was washed with water and n-hexane to obtain l- (4-trifluoromethoxyphenyl) -5- (4-cyano-2,5-di-fluoro-N-acetylanilino) ) tetrazole (1.55 g). Boiling point: 108-110.5 ° C Table 1 below shows the compounds obtained in the same manner as described in Synthesis Examples 1 to 6, together with the compounds obtained in the Synthesis Examples 1 to 6 above.

Table 1 Compound RLn R- R3m R "No. of fusion point (° C) or refractive index (n20D) 2 4-F 4-CN 2, 5-F2 CH 162.5 3 4-CF3 4-CN 2-Cl COOCH3 111- 112 4 4-CF3 4-CF3 2-Cl H 115.5-116.5 4-CF3 4-CN 2, 5-F2 SO2CH3 129.5-130.5 6 4-OCF3 4-CN 2, 5-F2 COCH3 108-110.-5 7 H 4-CN 2, 5-F2 H 171-172.5 8 2-Cl 4-CN 2, 5-F2 H 165-167-5 9 4-OCF3 4-CN 2, 5-F H 165-167.5 3-CN 4-CN 2, 5-F2 H 196-197 11 3-F 4-CN 2, 5-F2 H 172-175.5 12 4-F 4-CN 2, 5-F: H 165-167 13 2-F 4-CN 2, 5-F H 174-177 14 3-CF3 4-CN 2, 5-F_H 195.5-199.5 3-C1-4- 4-CN 2 f 5 -FH 136-136-5 OCF3 16 4-CF3 4-CN 2, 5-FH 171-172 7 3-CF3-4- 4-CN 2, 5- F: H 210-211 Cl 3 2-CF < 4-CN 2, 5-F_H 184.5-186.5 Table 1 (continued) Compound R'n R- R3m R "No. of fusion point (° C) or refractive index (n- ° D) 19 2, 4-Cl: 4-CN 2,5-F2 H 182-186.5 20 4- Cl 4-CN 2,5-F 2 H 185-188 21 3, 4-Cl: 4-CN 2,5-F 2 H 216-217-5 (decomposes) 22 2, 3-Cl 2 4-CN 2,5-F H 141-144.5 23 4-Br 4-CN 2,5-F 2 H 185-190 24 H * 4-CN 2,5-F 2 SO 2 CH 3 127.5-130 26 4-OCF3 4-CN 2,5-F2 SO2CH3 93-94.5 27 4-CF3 4-CN 2,5-F2 COCH3 110-111 29 4-F 4-CN 2,5-F 2 COCH 3 117.5-121.5 30 4-OCF, 4-CN 2-CF 3 H 137-138 31 4-F 4-CN 2-CF, H 149.5-151 Table 1 (continued ) Compound R1n R- R3m R4 point No. fusion (° C) or refractive index (n ¿D) 32 3-CF3 4-CN 2-CF3 H 176.5-178.5 33 3-C1-4- 4-CN 2-CF3 H 170-171 34 4-CF 3 4-CN 2-CF 3 H 152-152. 3-CF3-4- 4-CN 2-CF3 H 200-204.5 Cl 36 4-Cl 4-CN 2-CF3 H 159.5-162.5 37 3, 4-Cl: 4-CN 2-CF3 H 175-176.5 38 2,3-Cl 2 4-CN 2-CF5 H 142-147 39 4-Br 4-CN 2-CF3 H 168-171.5 40 2, 6-Cl: 4-CN 2-CF3 H 1.4720 41 3-C1-4- 4-CN 2-CF3 H 172-174 CF3 (decomposes) 43 3-F 4-CN 2-CF3 H 149-151 44 H 4-CN 2,5-F2 COOCH3 113.5-115 45 3-CN 4-CF3 2,6-Cl2 H 173-177 46 4-F 4-CF3 2,6-Cl2 H 167-169 47 4-OCF, 4-CF3 2,6-Cl: H 128-132 Table 1 (continued) Compound R n R R3m R4 point No. fusion (° C) or refractive index (n 0D) 48 4-OCF3 4-CN 2, 5-F2 COOC2H5 87-88.5 49 H 4-CN 2, 5-F COCH2OCH3 85-88.5 50 4-OCF3 4-CF3 2-C1- H 121-124 6-Br 51 H 4-CN 2,5-F2 CH3 132-132.5 52 3-CF3 4-CF3 2, 6- H 187-188 Cl2 (decomposes) 53 4 -NO; 4-CN 2, 5-F2 H 178.180.5 54 3-C1-4- 4-CF3 2, 6- H 148-152 OCF3 Cl2 55 4-CF3 4-CF3 2, 6- H 139.5-140 Cl: 56 3-CF3-4- 4-CF3 2, 6 - H 132-136 Cl Cl. 57 4-OCF 3 2-CN 3-FH 153-155.5 58 4-CF3 2-CN 3-F H 145.5-146.5 59 4-OCF3 2-CN 5-F H 138.5-140.5 Table 1 (continued) Compound R "n R" R3m R4 point No. fusion (° c) or refractive index (n 0D) 143.5-146.5 60 4-OCF3 4-CN 2, 5-F I ~ QG 129. 5-131.5 61 4-OCF3 4-CN 2,5-F2 X Q) 62 4-CF3 2-CN 5-F H 217-218 63 4-CF ^ 2-CN 5-C1 H 141-142 64 4-CFj 4-CN 2, 6- H 191.5-193 Cl2 (decomposes) 65 4-CF3 4-CF3 2-C1- H 192-193 6-Br 66 4-CF3 4-CN 2, 5-F2 COOCH3 148.5-149.5 67 3-CF3-4- 4-CF3 2-C1- H 162-163 Cl 6-Br 68 4-OCF 3 4-CN 2, 5-F 2 CH 3 111.5-112.5 69 4-OCF3 4-CN 2-F H 201.5-202.5 (decomposes) 70 4-CF3 4-CN 2-F H3 119-124 71 4-CF3 2-CN 3-F H 215-216 72 4-CF3 4-CN 2-Cl H 209-209.5 73 4-OCF3 4-CN 2-Cl H 183-186 Table 1 (continued) Compound R'n R R3m R "No. of fusion point (° C) or refractive index (n10D) 74 4-Cl 4-CN 2,5-F 2 CH 3 148-149.5 75 4-OCF 3 4-CN 2,5-F 2 CN 155-157 76 4-Cl 4-CF 3 2, 6- H 156-160 Cl 2 77 3, 4-Cl: 4- CF3 2.5-F2 CH3 150.5-152 78 2.3-Cl: 4-CN 2.5-F2 CH3 148.5-149.5 79 3.4-Cl_ 4-CF3 2, 6- H 151-155 Cl. 3, 4-Cl. 4-CN 2-Cl. H 230-232.5 (decomposes) 3-C1-4- 4-CN 2-CF3 H 148.5-152 CH3 82 4-CF3 4-CN 3-C1 H 207-210.5 (decomposes) 83 3-C1-4- 4-CN 3-C1 H 199-201.5 OCF3 (decomposes) Table 1 (continued) Compound R: n R2 R3m R4 point No. fusion (° C) or refractive index (n D) 84 4-Br 4-CN 2,5-F2 CH3 166-166.5 85 3-C1-4- 4-CN 2-Cl H 204.5-207.5 CF3 (decomposes) 86 2-CH3-4- 4-CN 2-CF3 H 153-155.5 Cl 87 2-Cl 4-CN 3-C1 H 219-223 (decomposes) 88 4-CH3 4-CN 2-CI3 H 109.5-112 89 3-CH3-4- 4-CN 2-CF3 H 101.5-104 Br 90 2-C1-5- 4-CN 2-CF3 H CF-, 91 3-C1-4- 4-CF3 2-F-6 - H 117-121 CF3 Cl 92 4-CF3 4-CF3 2-F-6- H 127.5-130 Cl 93 4-C1-4- 4-CF3 2-F-6- H 86.5-87.5 OCF-, Cl 94 4-CF, 2-CN 3-Cl H 192-195 Table 1 (continued) Compound RLn R2 R3m R4 point No. fusion (° C) 0 refractive index (n £ CD) 95 4-Cl 4-CN 2-F H 193-194 96 4-Br 4-CN 2-F H 182-186 97 4-Cl 2-CN 3-F H 173.5-174 (decomposes) 98 4-Br 2-CN 3-F H 99 4-Br 4-CF ^. 2-Cl H 103.5-104.5 100 3-F 4-CN 2-CF3 H 139.5-142.5 101 4-CFí 4-CN 2-Cl CH3 112-114 102 4-CF5 4-CN 2-OCF3 H 120-123.5 103 4-Cl 4-SO_CF3 2-Cl H 181.5-186.5 (decomposes) 104 4-Br 4-SO2CF3 2-Cl H 176-180 105 4-CF3 4-SO.CF3 2-Cl H 159-162 106 4-F 4-SOICFI 2-Cl H 148-151 Table 1 (continued) Compound R ~ n R- RJm R point No fusion (° c) or refractive index 111 4-Cl 4-SO CF 3 2-Cl H 112 4-Br 4-SO 2 C 2 H 5 2-Cl H-113 4-Cl 4 -SOrCH 3 2,5-F 2 H-114 4-CF 3 4 -NO: 2-Cl H - 115 4-CF3 4-SO: CH 2 -Cl CH 3 - 116 4-CF 3 4-CN 2.5-F 2 C HS - 117 4-CF 3 4-CN 2-CF 3 CH 3 - 113 3, 4-F: 4-CN 2,5-F2 CH3 123-125 119 4-CF3 2-CF3 4-Cl H 97-98 120 4-CF3 2-CF3 4-Cl COOCH3 115-119 121 4-CF3 2-CFj 4-Br H 107-109 122 4-CF3 2-CF3 4-Br COOCH3 115-117 123 4-Cl 4-CN 2-OCF3 H 134-135 124 4-SCF3 4-CN 2-CF3 H 157-158 125 4-SCF3 4-CN 2-Cl H 153-156 126 4-Cl 2-CN 4-CF3 H 149-153 127 4-SCF3 4-CN 2.5-F: H 157 128 4-Cl 4-CF 3 2.5- H 150.5-156-5 Cl; Table 1 (continued) Compound RLn R- R3m R ^ No. of fusion point (° C) or refractive index (n: D) 129 4-Cl 4-CFj 2,5-F2 COOCH3 1.5259 130 4-Cl 4- CF3 2.5-F2 H Cl: 132 3-C1-4- 4-CN 3 -FH 152-157 CH 3 134 4-CF 3 4-NO; 2-Cl H 135 4-CF, 4-COOCH 3 2-Cl H 136 4-CF 3 2 -COOCH 3 4-Cl H 137 4-Cl 4 -NO: 2-Cl H 133 4-Br 4 -COOCH 3 2-Cl H 139 4-Cl 4-CONH 2 2-Cl H 140 4-CF 3 4-CSNH: 2, 5-F: H 141 4-Cl 4-CSNH .. 2, 5-F: H 142 4-CF 3 4- 2, 5-F: H COOC; Hs 143 4-Cl 4- 2, 5-F: H COOC "H = Table 1 (continued) Compound R" n R¿ R3m R4 point Fusion No. (° C) or refractive index (n2? D) 144 4-Cl 4-NO: 2-FH 145 4-CF3 4-N0r 2-Cl CH3 146 4-Cl 4 -COOCH3 2-Cl CH 147 4-CF3 2-COOCH3 4-Cl CH3 148 4-Cl 4 -COOCH3 2.5-F: CH3 149 4-Cl 4 -COOCH3 2.5-F2 H 150 4-OCF3 4-NO: 2-Cl H 151 H 4 -COOCH3 2-Cl H 152 4-CF3 4-COOCH3 2-FH Examples of Use Example 1 Fungicide Test (Antimicrobial Activity on culture medium) Test Procedure In this test, the pathogenic microorganisms shown below were used: Pathogenic filamentous fungi for plants: Pyricularia oryzae, Botrytis cinerea, Sclerotinia sclerotiorum, Pathogenic bacteria for plants: Xanthomonas campestris pv. oryzae Pathogenic bacteria for animals: Staphylococcus aureus. A culture medium of potato / glucose agar was used for the preculture and the filamentous fungi test, and a semisynthetic potato culture medium was used for the preculture and the bacteria test. Each test compound dissolved in a small amount of methanol was suspended in distilled water and added to each medium at a concentration of 10 ppm. Fifteen ml of each medium to which the compound had been added were emptied into a Petri dish (diameter: 9 cm) and solidified. Subsequently, each test organism was grown on it. For the filamentous fungi, the precultured mycelial cluster was cut with a hole cutter (diameter: 4 mm) and the bunch or cut cluster was placed on a test medium for the culture. For bacteria, a small amount of the cells was inoculated into a medium with a platinum loop for stretch mark culture. After 7 days of cultivation for Pyricularia oryzae and after 2 days for the other pathogenic microorganisms, the diameter of the mycelial cluster (filamentous fungi) or the degree of cell growth (bacteria) was measured to obtain a percentage inhibition of growth on the medium .

Results Ninety-nine% or more of the antimicrobial activities were shown, respectively, by Compounds Nos. 9, 11, 12, 14, 16, 20, 23, 27 and 36 of the invention for Pyricularia oryzae; by Compounds Nos. 9, 11, 12, 14, 16, 20, 23, 27, 36 and 39 of the invention for Botrytis cinerea; for Compounds Nos. 9, 16, 20, 23 and 36 of the invention for Sclerotinia sclerotiorum; for Compounds Nos. 9, 16, 20, 23, 27, 36 and 39 of the invention for Xanthomonas campestris pv. oryzae; and for Compounds Nos. 9, 16, 20, 23, 36 and 39 of the invention for Staphyl ococcus a ureus.

Example 2 of Fungicide Test (Petri dish test for gray molds) Preparation of Wettable Powder Active compound: 30 to 40 parts by weight Carrier: a mixture of diatomaceous earth and kaolin (1: 5), 55 to 65 parts by weight Emulsifier: polyoxyethylene alkyl phenyl ether, 5 parts by weight The above-stated amounts of the active compound, the carrier and the emulsifier were pulverized and mixed to prepare the wettable powder, and the powder was diluted with water at each prescribed concentration of the active compound.

Test Procedure Approximately three beans or beans were planted (culture: serene) in a vinyl plastic pot (diameter: 7 c) and placed in a greenhouse at 15-25 ° C. To the small seedlings that reached a primary leaf stage, each test compound was applied, which had been diluted to a prescribed concentration as mentioned above, in the amount of 25 ml by three pots. The mycelial clusters of Bo tryti s cinerea that had been cultivated beforehand were cut, along with the medium, with a hole cutter to produce a cluster disk for 'inoculation. After 1 day from the application, the disc of the tuft or cluster was inoculated in the treated plants and kept in a humidity-temperature chamber of 20 ° C. After 4 days from the inoculation, the proportion of appearance in each mixture was classified and evaluated according to the following criteria to calculate a proportion of control. The results are shown by the average evaluation of three pots.

Apparition Ratio Dotted or Spotted Area Proportion (% or 0 0.5 less than 2 I 2 to less than 5 • - 5 to less than 10 Proportion of Appearance Dotted or Spotted Area Proportion (% 3 10 to less than 20 4 20 to less than 40 5 40 or more Control ratio (%) - (l-. {Proportion of occurrence in the treated area proportion of occurrence in the untreated area.}.) X 100 Results Compounds Nos. 9, 16, 20, 23 and 28 of the invention showed 95% or greater proportion of control at the concentration of 250 ppm.

R "Example 1 of Insecticide Test (Test against larvae Spodop tera l i tura Preparation of test solutions Solvent: 3 parts by weight of xylol Emulsifier: 1 part by weight of polyoxyethylene alkyl phenyl ether To produce a suitable preparation of the active compound, 1 part by weight of the active compound was mixed with the set amount of solvent containing the stated amount of the emulsifier, and the mixture was diluted with water to a prescribed concentration.

Test procedure Cabbage leaves (Ba ssi ca ol erácea) were immersed in the aqueous solution of the active compound at the prescribed concentration. After air drying of the solution, the treated leaves of cabbage were placed in a Petri dish (diameter: 9 c), and ten of the larvae in third stage of pupa of common nocturnal caterpillars (Spodop t era lit ura) were released. The box was then placed in an incubation chamber at 25 ° C. After 7 days, the number of dead larvae was examined to calculate mortality in%. The tests were successfully conducted twice and the mortality in or is shown in its average.

Results Compounds Nos. 1 to 5, 7 to 24, 26 to 39, 41 to 52, 60, 63, 65 to 67, 69 to 75, 77 to 31, 86, 88 to 106, 118 to 130 of the invention showed 100 % mortality at the 1000 ppm concentration.

Example 2 of Insecticide Test (Test against larvae of Aul acophora femorali s) Test Procedure Cucumber leaves were immersed in the aqueous solution of the active compound at the prescribed concentration. After air drying of the solution, the treated cucumber leaves were placed in a Petri dish (diameter: 9 cm), and ten of the larvae were released on. second stage of pupa leaf beetle chrysalis (Aul acophora femoral i s). The box was then placed er. an incubation chamber at 25 ° C. After 7 days, the number of larvae was examined to calculate mortality in%. The tests were successfully conducted twice and the destruction in% is shown in its average.

Resul ados Compounds Nos. 1 to 5, 7 to 40, 41 to 44, 47 to 49, 51, 60 to 62, 66, 69 to 75, 77, 78, 81, 83 to 90, 93 to 106, 118 to 130 of the invention showed 100% mortality at the concentration of 1000 ppm.

Test Example 1 Herbicide (Effect of herbicide test against weeds in rice fields) Preparation of formulations of the active ingredients carrier: acetone 5 parts by weight emulsifier: one part by weight of benzyloxy polyglycol ether The formulations of the active ingredients are obtained by mixing one part by weight of the active compounds and the above amounts of the carrier and the emulsifier. The prescribed amount of the formulation is diluted with water to prepare a test formulation.

Test Procedure In the greenhouse, of every 3 rice seedlings (crop: Níh onbare) of leaf stage 2.5 (15 cm high) they were transplanted in two places to 1/2000 in large pots (25 x 25 x 9 cm) filled with rice field. Subsequently, seeds of small flower, monochoria, broadleaf weeds (common false pimpernel, Indian tooth, long-stemmed aquatic grass, Ammanni a mul ti fl ora Roxb., Dopa tri um j unce um Hami lt, etc.) were sown. .) and rush were planted, and water on the ground at a depth of approximately 2-3 cm. Each prescribed amount of the active compound formulation prepared in a manner similar to those in the above preparation method was applied to the surface of the water 7 days after transplanting the rice plant. The herbicidal effect and the degree of phytotoxicity against the harvest plants was examined on the day after 3 weeks of treatment. During the test period the water depth of 3 cm was maintained. The herbicidal effect was rated as 100% in the case of complete death and 0% in the case where no herbicidal effect was observed, or in the case where phytotoxicity was not observed.

Results In this test, for example, Compounds Nos. 5, 6, 9, 11, 12, 16, 26, 27, 48 and 66 of the invention showed 90% or more of the herbicidal grade against the small flower, monochoria, weeds of broadleaf and reed by applying 0.5 kg / ha of the amount of the active compound.

Test Example 2 Herbicide (Pre-emergency soil treatment test centers plowed field weeds) Test Procedure In the greenhouse, seeds of PcZygom m bl u ei Mei ssn and Amaran th us li vídus were planted each in the topsoil of the plowed earth soil filled in a 120-acre pot with soil cover, and each prescribed amount of The test formulation prepared in a manner similar to those in Test Example 1 Herbicide was spread evenly over the topsoil in the test pot.The degree of herbicidal effect was examined after 4 weeks of the dispersion.

Results In this test, for example, Compounds Nos. 5, 6, 16, 27, 28, 48 and 66 of the invention showed 100% of the grade or proportion of the herbicide against Polygon um bl umei Mei ssn and Amaran th us li vi dus per application of 0.5 kg / ha of the amount of the active compound.

Test Example 3 Herbicide (Post-emergence foliage treatment test centers plowed field weeds) Test Procedure In the greenhouse, seeds of Polygon um bl umei Mei ssn and Amaran thus li vi dus were planted each in a 20 cm pot "filled with plowed soil and covered with soil." After 10 days from sowing and covering the soil (when the weeds were in the foliage stage 2 on average), spread evenly over the foliage part of the plants tested in the test pot, each prescribed amount of the formulation prepared in a similar way to that in Example 1 of herbicidal test.After 3 weeks from the dissemination, the degree of herbicidal effect was examined.

Results In this test, Compounds Nos. 5, 28, 48 and 66 of the invention showed 90% or more of the herbicidal grade against Polygon um bl umei Mei ssn and Amaran th us li vi dus per application of 0.5 kg / ha of the amount of the active compound.

Formulation 1 (granules Water (25 parts) is added to a mixture of Compound No. 3 of the invention (10 parts), bentonite (montmorillonite) (30 parts), talc (58 parts) and salt of lignin sulfonate (2 parts) with good kneading, and formed into 10-40 mesh granules using an extrusion type granulator followed by drying at 40-50 ° C to give granules. ^ d ^ - ° ^ § Formulation 2 (granules) A clay mineral (95 parts) having a particle size distribution within the range of 0.2-2 mm, is introduced into a rotary mixer and Compound No. 1 of the invention (5 parts) is sprayed therein with diluents Liquids under rotation to uniformly wet, followed by drying at 40-50 ° C, giving granules.

Formulation 3 (emulsion) An emulsion is obtained by mixing Compound No. 3 of the invention (30 parts), xylene (5 parts), polyoxyethylene alkylphenol ether (8 parts) and calcium alkylbenzenesulfonate (7 parts) with stirring.

Formulation example 4 (wettable powder) A wettable powder is prepared by mixing Compound No. 5 of the invention (15 parts), a mixture (1: 5) (80 parts) of White Charcoal fine powder of non-crystalline silicon oxide, hydrated) and clay in powder, sodium alkylbenzene sulfonate (2 parts) and a condensate of sodium alkylnaphthalene-suifcnate and formaldehyde (3 parts) in a powdery state.

Formulation Example 5 (wettable granules) Wettable granules are prepared by thoroughly mixing the compound No. 2 of the invention (20 parts), sodium lignin sulfonate (30 parts), bentcnite (15 parts) and diatomaceous earth powder, calcined (35 parts), followed by the addition of water and extrusion through a 0.3 mm mesh and drying.

It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention is that which is clear from the present description of the invention.

Having described the invention as above, the content of the following is claimed as property:

Claims (1)

1. ? is cyano, nitro, haloalkyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, haloalkylsulfonyl of 1 to 4 carbon atoms, (alkoxy of 1 to 4 carbon atoms) - carbonyl, aminocarbonyl or aminothiocarboni the, R 'is halogen, haloalkyl of 1 to 4 carbon atoms or haloalkoxy of 1 to 4 carbon atoms, R 'is hydrogen, cyano, alkyl of 1 to 4 carbon atoms, (alkyl of 1 to 4 carbon atoms) - carbonyl, (alkoxy of 1 to 4 carbon atoms) - carbonyl, alkylsulfonyl of 1 to 4 carbon atoms , (C 1 -C 4 alkoxy) (C 1 -C 4 alkyl) - carbonyl, phenoxycarbonyl, which may be substituted by nitro or pyridylcarbonyl, which may be substituted by halogen, n is 1, 2 or 3, and when n represents 2 or 3, two or three of R ~ may be the same or different, and m is 1 or 2, and when m represents 2, two of R 'may be the same or different. THE; 1-phenyl-5-anilinotetrazoles of . _i .. _ in accordance with the claim '_ ct ra; er? zaaos because it is hydrogen, halogen, cyano, nitro, alkyl 1 to 3 carbon atoms, fluoroalkyl of 1 to 3 carbon atoms, fluoroalkoxy of 1 to 3 carbon atoms or fluoroalkyl thio of 1 to 3 carbon atoms, R is cyano, nitro, haloalkyl of 1 to 3 carbon atoms, alkylsulfonyl of 1 to 3 carbon atoms, haloalkylsul fonyl of 1 to 3 carbon atoms, (alkoxy of 1 to 3 carbon atom) -carboxyl, aminocarbonyl or aminothiocarbonyl. R is halogen, fluoroalkyl of 1 to 3 carbon atoms, fluoroalkoxy of 1 to 3 carbon atoms, R is hydrogen, cyano, alkyl of 1 to 3 carbon atoms, (alkyl of ia 3 carbon atoms) - carbenyl, (alkoxy of 1 to 3 carbon atoms) - carconyl, alkylsulfonyl of 1 to 3 carbon atoms, ( C 1 -C 2 -alkoxy) -C 1 -C 2 -alkyl) -carbonyl, optionally nitro-substituted or optionally chloro-substituted pyridylcarbonium, n is 1 or 2, and when n represents 2, two of R "may be the same or different, and m is 1 c 2, and when m represents 2, two of R" may be the same or different. 3. The l-phenyl-5-anilinotetrazoles of the formula (I) according to claim 1, characterized in that R is hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, trifluoromethyl, tri-fluoroethoxy or trifluoromethythio, R "is cyano Nitro, trifluoromethyl, methylsulphonyl, ethylsul fonyl, tri-f luoromet ilsul fonyl, methoxycarbonyl, ethoxycarbonyl, aminocarbonyl or inotiocarbonyl R is fluorine, chlorine, bromine, trifluoromethyl or trifluoromethoxy R is hydrogen, cyano, methyl, Tilcarbonyl, methoxycarbonyl, ethoxycarbonyl, methylsulphonyl, ethoxymethylcarbonium, phenoxycarbonyl, 4-nor rhenoxycarbonyl or 2,6-dichloro-4-pyridylcarbonyl, n is 1 or 2, when n represents 2, two of R ~ can be equal or different, and.: is 1 or 2, when m represents 2, two of R "may be the same or different. 4. A process for the preparation of 1-phenyl-o-aniimotetrazoles of the formula (I), (I) characterized because? is hydrogen, halogen, cyano, nitro, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, haloalkoxy of 1 to 4 carbon atoms or haloalkylthio of 1 to 4 carbon atoms,? is cyano, nitro, haloalkyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, haioalky-suifonyl of 1 to 4 carbon atoms, (alkoxy of 1 to 4 carbon atoms) -carbonium, aminocarbonyl or aminothiocarbonium , or T - no > a _ or a? q \ a atoms or haloalkoxy of 1 a; p? carbon, Geno, cyano, alkyl of 1 to 4 atoms of ono, (alkyl of 1 to 4 carbon atoms) -: nyl, (alkoxy of 1 to 4 carbon atoms' -carbonium, alkyl Isul for.io from 1 to 4 carbon atoms, (atoxy of 1 to 4 carbon atoms) (alkyl of 1 to 4 carbon atoms) -carbonyl, phenoxycarboni, which may be substituted by nitro or pyridylcareonyl, which may be substituted by halogen, is i, 2 or 3, and when n represents 2 or 3, two or three of R can be the same or different, and is 1 or 2, and when m represents 2, two of R ~ are the same or different .- a; eei case d of R is hydrogen: the compounds of the formula R n They are defined above, and they are useful. where R ", R and m are as defined above, c essence oe; nte, y, si: S ac:? - sarU! í, acid link, in the case where R 'is alkyl of 1 to 4 carbon atoms or (acycxy of 1 to 4 atoms? • c p o f -c rbo ilo > moues =; * toror, mr. a4, e a where R, R, R, m and n are as defined an e io mind, and?. is alkyl of 1 to 4 carbon atoms or (akoxy of I to 4 carbon atoms) -carbonyl, 3e react with sodium azide, in the presence of a diluent, c) in the case where R "is hydrogen: the compounds of the formula - O and R n s orco: se aeti R is alkyl of 1 to 4 carbon atoms or optionally substituted with nitro, sor. hydrolysates in the presence of a diluent, and, if ropiado, the presence of a base, or d) in the case where R "are the radicals corro are defined for R" above, with the exception of The compounds of the formula .to; O Leiinen nar with the compounds of the formula: ÍV) and R's are radicals as defined for the P above, with the exception of hydrogen and alkyl of 1 to 4 carbon atoms, and Y is halogen, preferably chlorine or bromine, in the presence of an inert solvent, and, if appropriate, in the presence of a linking agent. acid, in the case where R "is (alkyl of 1 .roo: ar 'a.cox: ae: to ocno) of a? i - this = previously mentioned d ^, T - ar: on l formula is alkyl of 1 to 4 atoms of carbon or xi of 1 to 4 carbon atoms) - (alkyl of 1 to 4 carbon atoms), and orespc! of solvents And i i is iprop: .ado, Resistance of an acid catalyst 5. The insecticidal compositions, characterized perch, contain at least one I-phenyl-5-aniinotetrazole of the formula (I) according to claim 1. 6. The microbicidal compositions which are terized because they contain at least one 1-phenol-5-tetrahydrate of the formula 1) according to claim 1. 7. The characterized herbicidal compositions contain at least one 1-phenyl-5-anilinotetrazole formula (I) according to the claim A process to fight insects ne characterized because the l-phenyl5 - -: O Le.:; izeies of the formula (l) are of indication 1. 9. S I process to combat non-microorganisms; , characterized in that the l-pheni-5-azoles of the formula (I) are in accordance with claim 1. 10. The process for combating unwanted weeds, characterized in that the l-phenyi-5-anilinotetrazoies of the formula (I) are in accordance with claim 1. II. The use of the 1-phenyl-5-anilinotetrazoles, the formula (I) according to claim characterized in that they are to combat cra; no ladcs 12. The use of the 1-phenyl-5-anilinotetrazcles .a formula (I) according to the claim, characterized in that they are to combat insects not 13. The use of the 1-fenii-5-anilinotetrazcles 3. formula (?) According to claim a -.-. Etherized because they are for combating weeds not eaaas. 14. The process for the preparation of the chemistry of agricultural chemistry, characterized in that 1-phenol-5-anmotetrazoles of the formula (I) according to claim 1, are mixed with exfenscres and / or active agents of surface. R E SUBMIT THE INVENTION This invention refers to the new • o-an: .ofeofrazóles of the formula (I): where R ', R ", R", R ", m, and n have the meanings;": rded in the specification, the processes for preparation, and their use as microbicides, -aicotines, and / or herbicides.