Title of Invention	"INSECTICIDAL PHTHALAMIDE DERIVATIVES"
Abstract	Phthalamide derivatives represented by the formula wherein X represents hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, nitro, cyano, C1-C6-alkyl-sulfonyloxy, C1-C6-haloalkylsulfonyloxy, phenylsulfonyloxy, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkylsulfinyl-C1- C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6- alkylsulfonylamino, bis(C1-C6-alkylsulfonyl) amino or C1-C6-alkoxycarbonyl, n    represents 1, 2, 3 or 4, Y represents hydrogen, halogen, C1-C6alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, or cyano, m    represents 1, 2, 3 or 4.

Title of Invention

"INSECTICIDAL PHTHALAMIDE DERIVATIVES"

Abstract

Phthalamide derivatives represented by the formula wherein X represents hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, nitro, cyano, C1-C6-alkyl-sulfonyloxy, C1-C6-haloalkylsulfonyloxy, phenylsulfonyloxy, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkylsulfinyl-C1- C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6- alkylsulfonylamino, bis(C1-C6-alkylsulfonyl) amino or C1-C6-alkoxycarbonyl, n    represents 1, 2, 3 or 4, Y represents hydrogen, halogen, C1-C6alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, or cyano, m    represents 1, 2, 3 or 4.

Full Text	The present invention relates to novel phthalamide derivatives, to processes for their preparation and to their use as insecticides. ; Cenam phthalamide derivatives showing an action as insecticide are already known (cf. EP-A 0 919 542, WO 01/00575, JP-A 2001-64268, EP-A 1 006 107, JP-A 2003-40864, WO 01/21576 and WO 03/11028). Further, it is already knov/n that certain phthalamide derivatives show an action as pharmaceutical (cf. EP-A 0 119 428). The conventional phthalamide derivatives, however, axe not fully satisfactory in terms of effects as insecticide. There have now been found novel phthalamide derivatives of the following formula (I) (Formula Removed) wherein X represents hydrogen, halogen, C1-C6~alkyl, C1-C6-haloalkyl, nitro, cyano, C1-C6-alkyl- sulfonyioxy, C1-C6-haloalkylsulfonyloxy, phenylsulfonyloxy, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-alkylsulfonylamino, bis(C1-C6-alkylsulfonyl)amino or C1-C6-alkylcarbonyloxy, n represents 1, 2, 3 or 4, Y represents hydrogen, halogen, C1-C6alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-aikylthio. C1-C6baloalkylthio or cyano, rn represents 1, 2, 3 or 4, R represents C1-C6-alkyl, C1-C8-alkyl which is mono- or poly-substituted by substituents se- lected from the group consisting of cyano, nitro, C1-C6-alkylarimosulfonyl, NrN-di(C1-C6-alkyl)aminosulfonyl, C1-C6-alkyIsulfonylamino, N-C1-C6-alkylsulfonyl-N-C1-C6-alkylamino, C1-C6-alkyl-carbonylamino, halo-C1-C6-alkyl, N-C1-C6-alkyl-carbonyl-N-C1-C6-alkylamino, C1-C6alkyl-thiocarbonylamino, N-C1-C6-alkylthiocarbonyl-N-C1-C6-alkylamino, C1-C6alk-oxy-imino-C1-C6alkyl, C1-C6-alkyl-aminocarboriyl, N,N-di(C1-C6-aIkyl)-aminocarbonyI, C1-C6 -alkyl-aminthiocarbonyl, N,N-di(C1-C6-alkyl)-aminothiocarbonylJ C1-C6-alkoxy-carbo-nyiammo, C1-C6-aIkoxycarbonyl-C1-C6-alkylamino. C1-C6-alkylamino-carbonyloxy'. N,N- alkyl)aminosulfonyl, C1-C6-aIkylsulfonylamino, NrC1-C6-alkylsulfonyl-N-C1-C6-alkylamino, C1-C6-alkyl-carbonylamino, halo-C1-C6-alkyl, N-C1-C6-alkyl-carbonyl-N-C1-C6-alkylamino, C1-C6-allcyl-thiocarbonylamino, N-C1-C6-alkylthiocarbonyl-N-C1-C6-älkylarnino, C1-C6-alk-oxyimino-C1-C6-alkyl, C1-C6-alkyl-aminocarbonyl5 N5N-di(C1-C6-alkyl)-aminocaTbonyl, C1-C6-alkyl-aminotliiocarbonyl, N,N-di(C1-C6-alkyl)-aminothiocarbonyl, C1-C6-alkoxy-carbo-nylamino, C1-C6-aIkoxy-carbonyl-C1-C6-alkylamino, C1-C6-alkylarnino-carbonyloxy, di(C1-C6-alkyl)amino-carbonyloxy, C1-C6-alkoxy-thiocarbonylamino, C1-C6-aIkoxy-thiocar-bonyl-C1-C6-alkylarniao, C1-C6-alkylammo-thiocarbonyloxy, N,N-di(C1-C6-alkyl)-amino-thiocarbonyloxy, ' C1-C6-allcylthdo-carbonylanaiao, C1-C6-alkylthio-carbonyl-C1-C6-alkyl-amino, C1-C6-aIkylamino-carbonylthio, N,N-di(C1-C6-alkyl)amino-carbonylthio, C1-C6-alkyl-thio-thiocarbonylamino, C1-C6-alkylthio-thiocarbonyl-C1-C6-alkylamino, C1-C6-alkylarnino-thiocarbonylthio, N,N-di(C1-C6-alkyl)amino-tbiocarbonylthio, C3-C6-cycloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-allcylsulfmyl-C1-C6-al]kyl and C1-C6-alkylsulfonyl-C1-C6-aIkyl, or represents C3-C8-cycloalkyl which may be substituted by substituents selected from the group consisting of C1-C4-alkyl, C1-C4-alkyItliio or C1-C2-allcyltMo-C1-C2-aUcylJ R2 represents hydrogen or C1-C6-alkyl, R3 represents hydrogen or C1-C6-alkyl, A1 represents straight chain or branched chain C1-C6-aIkylene, C1-C8-haloalkylene, C2-C8-alke-nylene, C2-C8-haloalkenylene, C2-C8-alkynylene, C2-C8 -haloalkynylene, C1-C8-alkylene-amino, C1-C6-alkylene(C1-C6-alkylamino), C1-C8-alkyleneoxy or C1-C8-alkylenethio, r represents O or l, A2 represents straight chain or branched chain C1-C8-alkylene, C1-C8-haloalkylene, C2-C8-alke-nylene, C2-C8-haloalkenyleneJ C2-C8-alkynylene or C2-C8-haloalkynylene, s represents O or l, Q represents a 5- or 6-membered heterocyclic group containing l to 4 hetero atoms selected from O to 4 nitrogen atom, O to l oxygen atom, and O to l sulphur atom, however not containing an oxygen atom and a sulphur" atom at the same titne, and said heterocyclic group may have one to three (Figure Removed), one to three (Figure Removed), one (Figure Removed)or one as ring constituent, and said heterocyclic group may be optionally substituted with at least one or more substituents selected from the below-mentioned group of substituents W1 wherein said substituents may be identical or different, W1 represents halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-allcylsulfinyl3 C1-C6-alkylsulfonyl, C1-C6-haloalkyl, C1-C6-haloalkoxy, C1-C6-haloalkyltiiio, C1-C6-haloalkylsulfunyl, C1-C6-haloalkylsulfonyl, C3-C6-cycloalkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkylsul-fmyl-C1-C6-alkyl C1-C6-alkylsulfonyl-C1-C6-alkyl, E represents phenyl, biphenyl, naphthyl, pyridyl, pyridazidnyl, pyrimidinyl, pyrazmyl, thienyl, furyl or pyrrolyl, wherein said group is optionally mono- or poly-substituted by substituents selected from the group W2 wherein said substituents may be identical or different, W2 represents halogen, nitro, C1-C6-alkyl, C1-C-alkoxy, C1-C-alkylthio, C1-C6-alkylsulfinyl, Q-Cs-alkylsulfonyl, C1-C6-haloallcyl, C1-C6-haloalkoxy, C1-C6-haloalkylthio, C1-C6-haloalkyl-sulfinyl, C1-C6-haloalkylsulfonyl, C3-C6-cycloalkyl, C1-C6-alkylthio-C1-C6alkyl, C1-C6-al- kylsulfinyl-C1-C6-alkyl or C1-C6alkylsulfonyl-C1-C6-alkyl, or represents C1-C6-alkylene, C3-C6-haloalkylene, oxy-C2-C4-aliylene, oxy-C2-C4-haloalkylene, C2-C4-alkyleneoxy, C2-C4-haloalkyleneoxy, C1-C3-alkylenedioxy or C1-C3-haloalkylenedioxy, in case that W2 are two adjacent substituents. Depending, if appropriate, on the type and number of substituents, the compounds of the formula (I) can be present as geometncal and/or optical isomers, regioisomers and/or configurational isomers or isomer mixtures thereof of varying composition. What is claimed by the invention are both the pure isomers and the isomer mixtures. The compounds of the formula (I) of the present invention can be obtained, for example, by the following preparation processes (a), (b), (c), (d), (e) and (f): Preparation process (a): in case that R2 in the formula (I) represents hydrogen. A process of reacting compounds of the formula (II) (Figure Removed)wherein R1, X and n have the same definition as aforementioned, with compounds of the formula (IH) (Figure Removed)wherein R3, Y, m, A1, r, Q, A2, s and E liave Üie same definition as aforementioned., in the presence of inert solvents. Preparation process (b): in case that R3 in the formula (I) represents hydrogen atom. A process of reacting compounds of the formula (TV) .0 (Figure Removed)wherein X, n, Y, m, A1, r, Q, A2, s and E have the same definition as •aforementioned, with compounds of the formula (V) R1 (Figure Removed)wherein R1 and R2 have the same definition as aforementioned, in the presence of inert solvents, and if appropnate, in the presence of a base. Preparation process (c): A process of reacting a compound represented by the formula (VT) (Figure Removed)wherein X, n, R1 and R2 have the same definition as aforementioned, with the compounds of the-formula (IH), (Figure Removed)wherein R3, Y, m, A1, r, Q, A2, s and E have Ihe same definition as aforementioned, in the presence of inert solvents. Preparation process (d): in case that R3 in the formula (I) represents hydrogen atom. A process of reacting compounds of the formula (VE) (Figure Removed)wherein X, n, Y, m, A1, r, Q, A2, s and E have the same definition as aforementioned, with the compounds of the formula (V), (Figure Removed)wherein R] and R2 have the same definition as aforementioned, in the presence of inert solvents. Preparation process (e): A process of reacting a compounds of the formula (VHT) (Figure Removed) wherein X, n, R3, Y, m, A1, r, Q, A2, s and E have the same definition as aforementioned, with the compounds of the formula (V), (Figure Removed)wherein R1 and R2 have the same definition as aforementioned, in the presence of inert solvents. Preparation process (f): in case that R1 in the formula (I) represents C1-C6-alkylsulfmyl-C1-C6-alkyl or C1-C6-alkylsulfonyl-CrC5-aIkyl. A process of reacting compounds of the formula (Ii) (Figure Removed)wherein Rlf represents C1-C6-alkylmio-Ci-O6-alkvl, and X, n, R2, R3, Y, m, A1, r, Q, A2, s and E have the same definition as aforementioned, with an oxidizing agent in the presence of inert solvents. According to the present invention, Üie phthalamide derivatives of the aforementioned formula (I) show strong insecticidal action. The formula (I) provides a general definition of the phthalamide derivatives according to the invention. Preferred substituents or ranges of radicals listed in the formulae mentioned above and below are illustrated below: X preferably represents hydrogen, halogen, C1-C4-alkyl, C1-C4haloalkyl, nitro, cyano, C1-C4-aücylsulfonyloxy, C1-C4-haloalkylsulfonyloxy, phenylsulfonyloxy, alkyl, C1-C4-alkylsulfmyl-C1-C4-alkylJ C1-C4-alkylsulfonyl-C1-C4-alkyl, C1-C4-alkylsulfonyl-amino, bis(C1-C4-alkylsulfonyl)amino or C1-C4-alkylcarbonyloxy. X particularlv preferably represents hydrogen, fluorine, chlorine, bromine, iodine, rnethyl, ethyl, n- or iso-propyl, n-, see-, iso- or tert-buryl, trifluoromethyl, difluoromethyl, dichloro- fluoromethyl, trichloromethyl, nitro, cyano, methylsulfonyloxy, ethylsulfonyloxy, trifluoro- methylsulfonyloxy, phenylsulfonyloxy, methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylüiioethyl, me&ylsulfinylmethyl, methylsulfinylethyl, ethylsulftnylmethyl, ethyl- • sulfinylethyl, memylsulfonyhnethyl, methylsulfonylethyl, ethylsulfonylmethyl, ethylsulfo- nylethyl, methylsulfonylamino, ethylsulfonylamino, di(methylsulfonyl)amino, di(ethylsulfo- nyl)amino, methylcarborryloxy or ethylcarbonyloxy. X very particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, tert-buryl, trifluoromethyl, nitro, cyano, methylsulfonyloxy, ethylsulfonyloxy, trifluoro-methylsulfonyloxy, phenylsulfonyloxy, methylsulfonylamino, di(methylsulfonyl)amino or methylcarbonyloxy. n preferably represents l, 2 or 4. n particularlv preferably represents 1. n furthermore, particularlv preferablv represents 2. • n furthermore, particularly preferablv represents 4. Y preferably represents hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-aIkyltnio, C1-C4-haloalkylthio or cyano. Y particularlv preferablv represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n- or iso-propyl, n-, see-, iso- or tert-butyl, trifluoromethyl, difluoromethyl, dichlorofluoromethyl, trichloromethyl, methoxy, ethoxy, n- or iso-propoxy, n-, see-, iso- or tert-butoxy, trifluoromethoxy, methylthio, ethylthio, n- or iso-propylthio, n-, see-, iso- or tert-butylthio, trifluoromethylthio or cyano. Y very particularly preferably represents hydrogen, chlorine, methyl, trifluoromethyl, methoxy or trifluoromethoxy. m preferably represents l or 2. m particularlv preferablv represents 1. m furthermore, particularlv preferablv represents 2. R1 preferably represents C1-C6-alkyl, C1-C6-aIkyl which is mono- or poly-sübstituted by substi-tuents selected from the group consisting of cyano, nitro, C1-C4-aUcylammosulfonyl, N,N-di(C1-C4-alkyl)aminosulfonyl, C1-C4-alkylsulfonylamino, kylamino, C1-C4-alkyl-carbonylarnino, halo-C1-C4-alkyl, N-C1-C4-alkyl-carbonyl-N-C1-C4-alkylamino, C1-C4-alkyl-tMocarbonylamino, N-C1-C4-alkylfhiocafbonyl-N-C1-C4-alkyl-amino, C1-C4-alkoxyimino-C1-C4-alkyl, C1-C4-alkyl-ainmocarbonyl3 N,N-di(C1-C4-alkyl)-aminocarbonyl, C1-C4-alkyl-ainniothiocarbonyl3 N-di(C1-C4-alkyl)-aminothiocarbonyl, C1-C4-alkoxy-carbonylamino3 C1-C4-alkoxy-carbonyl-C1-C4-alkylamino, C1-C4-alkylaraino-car-bonyloxy, N,N-di(C1-C4-alkyl)araino-cärbonyloxy3 C1-C4-alkoxy-fhiocarbonylamino) C1-C4-alkoxy-tlxiocarbonyI-C1-C4-alkylamino3 C]-C/)-alkylamino-thiocarbonyloxy, N,N-di(C1-C4-alkyl)aniino-thiocarbonyloxy, C1-C4-aIkylthio-carbonylaminoJ C1-C4alkyltliio-carbonyl-C1-C4-alkylamino, C1-C4-alkylaniino-carbonylthio) N,N-di(C1-C4-alkyl)arnino-carbonyl C1-C4-alkylthio-thiocarbonylamino3 C1-C4-allcylthio-1;hiocarbonyl-C1-C4-alkylaniino3 C1-C4-al-kylamino-thiocarbonylthio, N,N-di(C! -C4-alkyl)amiQO-fhiocarbonylthio3 C3-C6-cycloaIkyl3 C1-C4-alkoxy-C1-C4-alkyl, C1-C4-allcylthio-C1-C4-alkyI3 C1-C4-alkylsulfinyl-C1-C4-alkyl and C1-C4-alkylsulfonyl-C1-C4-alkyl3 or represents C3-C6-cycloalkyl which may be substituted by C1-C2-alkyl3 C1-C2-alkylthio or C1-C2-alkyltfaio-C1-C2-alkyl. R1 particulariv preferablv represents methyl, ethyl, n- or iso-propyl, n-3 see-, iso- or tert-butyl, n-pentyl, 1-methylbutyl, 1-ethylpropyl, n-hexyl3 1,3-dimethylbutyl; methyl, ethyl, n- or iso-propyl, n-, see-, iso- or tert-butyl, each of which is mono- or poly-substituted by substituents selected from the group consisting of c}'ano, nitro, methylarninosulfonyl., ethylaminosulfonyl, • N,N-di(methyl)arninosulfonyl, N,N-di(ethyl)aminosulfonylJ methylsulfonylamino, ethylsul-fonylamino, N-methylsuUbnyl-N-methylamino, N-ethjdsulfonyl-N-methylamino, N-methyl-sulfonyl-N-ethylamino, N-ethylsulfonyl-N-ethylamino, methyl-carbonylamino, ethyl-cafbo-nylamino, trifluoromethyl, pentafluoroeth}'!, N-methyl-carbonyl-N-methylamino, methyl-thiocarbonylamino, ethyl-thiocarbonylamino, N-methylthiocarbonyl-N-methylamino, meth-oxyimino-methyl, methoxyimino-ethyl, eüaoxyimino-methyl., ethoxjdmino-ethyl, methyl-aminocarbonyl, ethyl-aminocarbonyl, N,N-di(methyl)-aminocarbonyl, N,N-di(ethyl)-amino-carbonyl, methyl-arnmothiocarbonyl, ethyl-aminothiocarbonyl, N3N-di(methyl)-aminotiiio-carbonyl, N,N-di(ethyl)-aminotliiocarboriyl., methoxy-carbonylarnino, ethoxy-carbonylamino, methoxy-carbonyl-methylamino, eüioxy-carbonyl-methylamino, methoxy-carbonyl-ethyl-amino, ethoxy-carbonyl-ethylamino, methylamino-carbonyloxy, etiiylamino-carbonyloxy, N,N-di(methyl)amino-carbonyloxy, N,N-di(ethyl)amino-carbonyloxy, methoxy-thiocarbo-nylamino, ethoxy-thiocarbonylamino, methoxy-thiocarbonyl-methylamino, methoxy-thiocar-bonyl-ethylamino, ethoxy-thiocarbonyl-methylamino, ethoxy-thiocarbonyl-ethylamino, me-thylamino-tiiiocarbonyloxy, ethylamino-thiocarbonyloxy, N,N-di(methyl)amiao-thiocarbo-nyloxy, N,N-di(ethyl)amino-thiocarbonyloxy, methylthio-carbonylamino, ethylthio-carbonyl-amino, methylthio-carbonyl-methylamino, ethylthio-carbonyl-methylamino, methylthio-car-bonyl-ethylamino, ethylthio-carbonyl-ethylamino, methylamino-carbonylthio, ethylamino-carbonylthio, N,N-di(methyl)amino-carbonylthio, N,N-di(ethyl)amino-carbonylthio., methyl- thio-thiocarbonylamino., ethylthio-thiocarbonylamiao, methylüiio-tliiocarbonylrmethylamino, ethylfhio-tlTiocarbonyl-methylamino, methylthio-thiocarbonyl-ethylainino, ethylthio-thiocar-bonyl-ethylarnino, methylamino-thiocarbonylthio, ethylamino-fhiocarbonylthio, N,N-di(me-thyl)amino-thiocarbonyithio, N,N-di(methyl)aimno-ti:tiocarbonylthio, cyclopropyl, cyclopen-tyl, cyclohexyl, metiioxy-methyl, ethoxy-methyl, methoxy-ethyl, ethoxy-ethyl, methyltbio-methyl, ethylthio-methyl, methylthio-ethyl, ethylthio-ethyl, methylsulfinyl-methyl, ethylsulfi-nyl-methyl, methylsulfinyl-ethyl, ethylsulfinyl-ethyl, methylsulfonyl-methyl, ethylsulfonyl-methyl, methylsulfonyl-ethyl, and ethylsulfonyl-ethyl; or represents cyclopropyl, cyclopen-tyl, cyclohexyl., each of which may be substituted by substituents selected from the group consistmg of methyl, ethyl, methylthio, ethylthio, methylthiomethyl, ethylthiomethyl, methylthioethyl and ethyltbioethyl. R1 very particularly preferably represents methyl, ethyl, n- or iso-propyl, n- or sec-buryl, n-pentyl, 1-methylbutyl, 1-ethylpropyl, 1,3-dimethylbutyl; methyl, ethyl, n- or iso-propyl, n-, see-, iso- or tert-butyl, each of which is mono- or poly-substituted by substituents selected from the group consisting of cyano, methylaminosulfonyl., ethylaminosulfonyl, N,N-di- (meth}'l)aminosulfonyl, N,N-di(ethyl)aminosulfonyls N-methylsulfonyl-N-methylammo, me-thyl-carbonylamino, trifluoromethyl, pentafliaoroethyl, methoxyimino-methyl, methoxy-imino-ethyl, ethoxyimino-methyl, ethoxyimino-ethyl, methyl-aminocarbonyl, ethyl-amino-carbonyl, N5N-di(methyl)-aminocarbonyl, N,N-di(ethyl)-aminocarbonyl, methyl-aminothio-carbonyl, ethyl-aminothiocarbonyl, N,N-di(rn.ethyl)-aminothiocarbonyl5 N,N-di(ethyl)-ami-nothiocarbonyl, methoxy-carbonylamino, methylarnino-carbonyloxy, ethylamino-carbonyl-oxy, N,N-di(methyl)arnino-carbonyloxy, N,N-di(ethyl)amino-carbonyloxy, methylamino-thiocarbonyloxy, N,N-di(methyl)amino-thiocarbonyloxy, metitylammo-carbonylthio, ethyl-amino-carbonylüiio, methylaniino-thiocarbonylthio, eüiylamino-tliiocarbonylthio, cyclohexyl, methoxy-methyl, ethoxy-methyl3 methylthio-methyl, methylsulfinyl-methyl and methylsulfonyl-methyl; or cyclopropyl, cyclopenlyl, cyclohexyl, each of which may be substituted by substituents selected from the group consisting of methyl, methylthio and metliyl-thiomethyl. R2 preferably represents hydrogen or C1-C4-alkyl. R2 particularlv preferablv represents hydrogen, methyl or ethyl. R2 yery particularly preferably represents hydrogen or ethyl. R3 preferably represents hydrogen or C1-C4-alkyl. R3 particularlv preferablv represents hydrogen, methyl, ethyl, n- or iso-propyl. R3 very particularly preferably represents hydrogen, methyl, ethyl or iso-propyl. A1 preferably represents straigbt chain or branched chain C1-C6-alkylene, C1-C6-haloalkylene, C2-C6-alkenylene, C2-C6-haloalkenylene, C2-C6-alkynylene3 C2-C6-haloalkynylene., C1-C6-al-kylene-amino, C1-C6-altylene(C1-C4-alkylamino), C1-C6-alkyleneoxy or C1-C6-alkylenethio. A1 particularlv oreferablv represents -CH2-, -(CH2)2-3 -(CH2)3-, -CH(CH3)-3 -OCH2-, -CH20.-, -O(CH2)2-, -(CH2)2O-3 -SCH2-3 -CH2S-3 -S(CH2)2- or-(CH2)2S-. A1 very particularly preferably represents -CH2-, -(CH2)2-3 -CH(CH3)-, -OCH2-, -O(CH2)2- or -CH2S-. r preferably represents 0. r furthermore preferably represents l. A2 preferably represents straight chain or branched chain C1-C6-alkylene, C1-C6-haloaIkylene5 C2-C6-alkenylene, C1-C-haloalkenylene, C2-C6-aIkynylene or C2-C6-haloall Tiylene. A2 tiarticularlv preferablv represents -CH2-, -(CH2)2-3 -(CH2)3-3 -CH(CH3)-3 -CH2-CH=CH-. s preferably represents 0. s furthermore. preferably represents 1. Q preferably represents pyridinylene, pyridazinylene, pyrirnidinylene, pyrazinylene, each of which is optionally mono- or poly-substituted by substituents selected frorn group W1 wherein said substituents may be identical or different, or further represents the below-mentioned groups; (Figure Removed) (Avherein the bond märked with * connects with A1 and the bond märked with # connects with A2, or the bond märked with # connects with A1 and the bond märked with * connects withA2) Q particularlv preferablv represents Q15, Q17, Q22, Q23, Q29, Q34, Q35, Q45, Q4S, Q50, Q55, Q56, Q58, Q59, Q60, Q61, Q62, Q63, Q64, Q66 and Q69. Q very particularly preferably represents Q15. Q furthermore very particularly preferably represents Q17. Q furthermore very particularly preferably represents Q22. Q furthermore very particularly preferably represents Q23. Q furthermore very particularly preferably represents Q29. Q furthermore very particularly preferably represents Q34. Q furthermore very particularly preferably represents Q35. Q furthermore very particularly preferably represents Q45. Q furthermore very particularly preferably represents Q48. Q furthermore very particularly preferably represents Q50. Q- furthermore very particularly preferably represents Q55. Q furthermore very parücularly preferably represents Q56. Q furthermore very particularly preferably represents Q5 8. Q furthermore very particularly preferably represents Q59. Q furthermore very particularly preferably represents Q60. Q furthermore very particularly preferably represents Q61. Q furthermore very particularly preferably represents Q62. Q furthermore very particularly preferably represents Q63. Q furthermore very particularly preferably represents Q64. Q furthermore very particularly preferably represents Q66. Q furthermore very particularly preferably represents Q69. W1 preferably represents halogen, C1-C4-alkyl, C1-C4-alkoxy5 C1-C4-alleylthio, C1-C4-alkylsulfrnyl, C1-C4-alkylsulfonyl, C1-C4-haloalkyl, C1-C4-haloaIkoxy, C1-C4haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C3-C6-cycloalkyl, C1-C4-alkylthio-C1-C4- alkyl, C1-C4-alkylsulfinyl-C1-C4-alkyl, C1-C4-alkylsulfonyl-C1-C4-alb>d. W1 particularlv preferablv represents methyl, ethyl, methoxy, methylthio, memylsulfmyl or methylsulfonyl. W1 very particularly preferably represents methyl. E preferably represents phenyl, biphenyl, naphthyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, thienyl, furyl or p)Trolyl, wherein said group is optionally mono- or poly-substituted by sub-stituents selected from the group W2 wherein said substituents may be identical or different. E particularlv preferablv represents phenyl, biphenyl, 3-pyridyl, 2-thienyl, 2-furyl or 2-pyrrolyl, wherein said group is optionally mono- to tetra-substituted by substituents selected from the group W2 wherein said substituents may be identical or different. E very particularly preferably represents phenyl, biphenyl, 3-pyridyl or 2-thienyl, wherein said group is optionally mono- to tetra-substituted by substituents selected from the group W2 wherein said substituents may be identical or different. W2 preferably represents halogen, nitro, C1-C4-alkyl, C1-C4alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloallcyl, C1-C4haloalkoxy, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloaUcylsulfonyl, C3-C6-cycloalkyl, C1-C4alkylthio-C1-C4 alkyl, C1-C4-alkylsulfinyl-C1-C4-allcyl or C1-C4-allcylsulfonyl-C1-C4-allcyl, or represents C3-C5-alkylene, C3-C5-haloalkylene, oxy-C2-C4-alkylene, oxy-C2-C4-haloallcylene, C2-C4-alky-leneoxy, C2-C4-haloalkyleneoxy, C1-C3-alkylenedioxy or C1-C3-haloaIkylenedioxy, in case W2 are two adjacent substituents. W2 particularlv preferablv represents fluorine, chlorine, bromine, nitro, methyl., ethyl, n- or iso-propyl, n-, see-, iso- or tert-butyl, methoxy, ethoxy, n- or iso-propoxy, n-, see-, iso- or tert-butoxy, trifluoromethoxy, diiluorometlloxy, methylthio, ethylthio, n- or iso-propylthio, n-, see-, iso- or tert-butylthio, trifiuoromethyl, difluoromethyl, dichlorofiuoromethyl, trichloro-methyl, trifluoromethoxy, difluoroniethoxy, trifluoromethylthio, or represents -OCF2O, -0(CF2)2O-, -OCHFCF20-, -OCF2CHFO-, in case W2 are two adjacent substituents. - W2 very particularly preferably represents fluorine, chlorine, bromine, nitro, methyl, ethyl, iso-propyl, methoxy, trifluorornethoxy, difluoromethoxy, methylthio, trifluoromethylthio, or represents -OCF2O~, -O(CF2)2O-, -OCHFCF20-, -OCF2CHFO-, in case W2 are two adjacent substituents. W3 represents hydrogen or has the same definition as the aforementioned W1, W3 preferably represents hydrogen, rnethyl, trifluoromethyl or methylthio. p represents O, l or 2. - P preferably represents 0. p furthermore preferably represents 1. q represents O, l, 2 or 3. q preferably represents 0. q furthermore preferably represents l. Compounds of formula (T), in which r is O and s is O are preferred. Compounds of formula (I), in which r is l and s is l are preferred. Compounds of formula 00, in which r is l and s is O are particularly preferred. Compounds of formula (I), in which R2 and R3 are both hydrogen are preferred. Compounds of formula (T), in which n is l and X is located in 3-position are preferred. Compounds of formula (I), in which X is iodine are preferred. Compounds of formula (T), in which Y is methyl are preferred. Compounds of formula (T), in which A1 is -CH2- are preferred. Compounds of formula (I), in which E is mono- to tetra-substituted phenyl, where the substituents are selected firom the group W2, are preferred. Compounds of formula (T), in which Q is Q66 are preferred. The general or preferred radical definitions or illustrations h'sted above apply both to the end products and, correspondingly, to the starting materials and intermediates. These radical definitions can be combined with one another as desired, i.e. including combinations between the respective preferred ranges. Preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being preferred. Particular preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred. Very particular preference according to the invention is given to the compounds of the formula (T) which contain a combination of the meanings listed above as being very particularly preferred, In the radical defmitions given above and below, carbon radicals, such as alkyl, are in each case straight-chain or branched as far as this is possible - including in combination with hetero atoms such as alkoxy. The aforementioned preparation process (a) can be illustrated by the following reaction scheme in case, for example, that 3-(l,l-dirnethyl-2- memylthioemylimino)-4-iodo-3H-isobenzofuran-l-one and l-(4-amino-3-methylbenzyl)- 4-(4-trifiuoromethylphenyl)-l,4-dihydrotetrazol-5-one are used as startingmaterials. (Figure Removed)The aforementioned preparation process (b) can be illustrated by the following reaction scheme in case, for example, that 2-{2-methyl-4-[5-oxo-4-(4-trifluorometh.ylphenyl)-4,5-dihydrotetrazol-l-yl-methyl]phenyl}isoindole-l.,3-dione and sec-butylamine are used as starting materials. (Figure Removed)The aforementioned preparation process (c) can be illustrated by the following reaction scheme in case, for example, that N-(l-methyl-propyl)phthalamic acid and i-(4-amino-3-metrrylbenzyl)-4-(4-trifiuoromethylphenyl)-l,4-dihydrotetra2ol-5-one are used as starting materials. (Figure Removed)The aforementioned preparation process (d) can be.illustrated by the following reaction scheme in case, for example, that l-[4-(3-oxo-3H-isobenzoflu:an-l-ylideneamino)-3-rnetliyl-benzyl]-4-(4-tri-fluoromethyl-phen3'l)-l,4-dihydrotetrazol-5-one and sec-butylarnine are used as starting materials. P The aforementioned preparation process (e) can be illustrated by the following reaction scheme in case, for example, thatN-{2-methyl-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-4,5rdihydro-tetrazol-l-yl-methyl]-phenyl}-phthalamic acid and sec-butylamine are used as starting materials. OH The aforementioned preparation process (f) can be Illustrated by the following reaction scheme in case, for example, that N2-(l3l-dimethyl-2-methylthioethyl)-3-iodo-N1-[2-methyl-4-(5-oxo-4-(4-tri-iluorometlaylphenyl)-4,5-dihydro-tetrazol-l-ylmet:hyl)-phenyl]-phthalamide and m-chloroperbenzoic acid are used as starting materials. (Figure Removed)The compounds of the formula (ü), starting material in the above-mentioned preparation process (a), are per se known compounds and can be easily prepared according to the process described in, for example, EP-A O 919 542, EP-A l 006 107. As specific examples of the compounds of the formula (ü) used as starting material in the preparation process (a) there can be mentioned the following: 3-isopropylimino-3H-isobenzofuran-1-one, 4-fiuoro-3-isopropyliirrmo-3H-isobenzofuran-l-one, 4-cbloro-3-isopropylimino-3H-isobenzofuran-l-oiie3 4-bromo-3-isopropylimino-3H-isobenzofuran-1 -one, 4-iodo-3-isopröpyliaiino-SH-isobenzoiuran-1-one3 3-isopropylirnino-4-nitro-3H-isobenzožuran-1 -one, 3-isopropylimmo-5-nitro-3H-isobenzofuran-l-one, 3-(l -methyl-2-methylsiilfanyl-etb.ylimino)-3H-isobenzofuran-1 -one, 4-fluoro-3-(l-methyl-2-meth}'lsulfanyl-ethylimino)-3H-isobenzofuran-l-one, 4-chloro-3 -(l -methyl-2-methylsulfanyl-ethylimino)-3H-isobenzofuran-1 -one, 4-bromo-3-(l-methyl-2-methylsulfanyl-ethyliiriino)-3H-isobenzofln:an-l-one, 4-iodo-3-(l -methyl-2-methylsulfanyl-ethylimino)-3H-isobenzoiuran-1 -one, 3 -(l -met3iyl-2-methylsulfanyl-ethylimino)-4-nitro-3H-isobenzoiuran-1 -one, 3-(l, l -dime1±iyI-2-meth)dsulfanyl-ethylimino)-3H-isobenzofuran-1 -one, 3-( l, l -dimethyl-2-methylsulfanyl-ethylirnino)-4-fluoro-3H-isobenzofuran-1 -one, 4-chloro-3-( l, l -dimethyl-2-methylsulfanyl-e1hyliniino)-3H-isobenzofaran-1 -one, 4-bromo-3 -(1,1 -dimethyl-2-methylsulfanyl-ethylimino)-3H-isobenzofuran-1 -one, 3-( l, l -methyl-methithylsulfanyl-ethyliminol-iodo-SH-isobenzofuran-1 -one, 3-(l,l-dÜTiethyl-2-methylsulfanyl-et3b.ylijnino)-4-rdtro-3H-isoben2ofiiran-l-one3 3-( l, l -dimethyl-2-methylsulfanyl-ethyliinmo)-4-methyl-3H-isobenzofuran-1 -one, 3-(l,l-methyl-2-methylsidfanyl-ethylmino)-5-methyl-3H-isobenzofuran-l-one, 4,7-dicKloro-3-(l,l-dimethyl-2-methylsulfanyl-eÜiyliriiino)-3H-isobenzofuran-l-one, 5,6-dichloro-3 -(1,1 -dimethyl-2-methylsulfanyl-ethylirnino)-3H-isobenzofuran-1 -one, 4,5,6,7-te1racbJoro-3-(l,l-dimethyl-2-me1hylsdfanyl-aylimino)-3H-isobenzofuran- l-one, 3-isopropylinoino-l-oxo-l,3-dihydro-isobensoiui'an-4--ylmethanesulfonate, 3 -(l -methyl-2-methylsulfanyl-etliyliniino-1 -oxo-1,3 -dihydro-isobenzofiiran-4-yl methanesulfonate, 3 -(l, l -dimethyl-2-methylsulfanyl-etliylimino-1 -oxo-1,3 -dihydro-isobenzofuran-4-yl methanesulfonate. The compounds of the formula (UI), starting material in the above-mentioned preparation process (a), include novel compounds not mentioned in the existing literatui"e as a part. Their corresponding anilines can be obtained, for example, by a catalytic hydrogen reduction, a well-known process in the field of organic chemistry, by reduciag compounds of the formula (Figure Removed)wherein Y, m, A1, r, Q, A2, s and E have the same definitions as aforementioned with hydrogen in the presence of a catalytic reduction catalyst, for example, palladium carbon, Raney nickel, platinum oxide. Compounds of the formula (HT), in which R3 corresponds alkyl, can be obtained by formylating the amino group of the anilines, further alkylating and then de-formylating. Moreover, compounds of the formula (UI), in which R3 corresponds alkyl, can also be obtained by preparing a Schiff base complex by a reaction of the anilines obtained by the reduction of compounds of the formula (DQ and a ketone or an aldehyde and then by catalytically reducing it. The compounds of the above-mentioned formula (IX) are, as will be described later in detail, novel compounds. As specific examples of the compounds of the formula (IH) there can be mentioned, for example, l -(4-amino-3-methyl-benzyl)- IH-pyrazole, l -(4-amino-3-methyl-benzyl)-3-methyl- IH-pyrazole, l -(4-arnino-3-methyl-benzyl)-4-methyl- IH-pyrazole., l-(4-amino-3-methyl-benzyl)-4,5-dichloro-lH-imidazole., l-(4-amino-3-methyl-benzyl)-lH-l,2,3-triazole, l -(4-amino-3-methyl-benzyl)- 1H-1,2,4-triazole, l-(4-amino-3-methyl-benzyl)-lH-tetrazole, l-(4-amino-3-methyl-benzyl)-5-methyl-lH-tetrazole, l-(4-amino-3-methyl-benz)4)-5-(2-chloro-phenyl)-lH-tetrazole3 l-(4-ammo-3-me1iyl-benzyl)-5-(3-trifluoromethyl-phenyl)-lH-tetrazole, l-(4-amino-3-methyl-benzyl)-5-(4-trifluoromethyl-phenyl)-lH-tetrazole, l-(4-amino-3-methyl-benzyl)-5-(3,5-bis-trifluoromethyl-phenyl)-lH-tetrazole, l-(4-amino-3-methyl-benzyl)-5-(3-trifluoromethoxy-phenyl)-lH-tetrazole., l-(4-arnino-3-methyl-berrzyl)-3-(4-1rifluoromethyl-phenyl)-iniidazolydin-2-one, l-(4-amino-3-methyl-benzyl)-3-(4-trifluoromethyl-phenyl)-l,3-dihydro-iinidazol-2-one, !-(4-amino-3-m.etliyl-beiTzyl)-3-(4-1rifluoromethyl-phenyl)-irnidazolydin-2,4-dione3 l-(4-ammo-3-methyl-benzyl)-3-(4-trifluoromemyl-phenyl)-irnidazolydin-2,435-trione, l-(4-aniino-3-methyl-benzyl)-3-(4-triflüoromethyl-phenyl)-lH-pyrazole] . 4-(4-amino-3-methyl-benzyl)-2-(2-fluoro-phenyl)-2,4-dihydro-l,2,4-triazol-3-one, 4-(4-ammo-3-methyl-benzyl)-2-(2-chloro-phenyl)-2,4-dihydro-l52,4-triazol-3-one, 4-(4-amino-3-methyl-benzyl)-2-(2-trifluororüethyl-phenyl)-2,4-diliydro-1,2,4-triazol-3 -one, 4-(4-amino-3-methyl-benzyl)-2-(3-fluoro-phenyl)-2,4-dihydro-l,2,4-triazol-3-one, 4-(4-amino-3-methyl-benzyl)-2-(3 -chloro-phenyl)-2,4-dihydro-1,2,4-triazol-3 -one, 4-(4-ammo-3-metiyl-benzyl)-2-(3-trifluoromethyl-phenyl)-2,4-dihydro-l,2,4-triazol-3-one 2-(4-fluoro-phenyl)-4-(4-amino-3-methyl-benzyl)-2,4-dihydro-l32,4-triazol-3-one3 . 4-(4-amino-3-methyl-benzyl)-2-(4-chIoro-phenyl)-2,4-diliydro-l.,2.,4-triazol-3-oneJ-4-(4-amino-3 -methyl-benzyl)-2-(4-trifluorometh.yl-phenyl)-2,4-dihydro-1,2,4-triazol-3 -one, 4-(4-ammo-3-methyl-benzyl)-2-(3,4-bis-trifluoromethyl-phenyl)-2,4-dihydro-l,2,4-triazol-3-one, • 4-(4-amino-3-methyl-benzyl)-2-(3,5-bis-tri£luoromethyl-phenyl)-2,4-dihydro-l,2,4-triazol-3-oneJ 4-(4-ainino-3-methyl-beil)-5-trifluoromethyl-2-(4-Mfluoromethyl-phenyl)-2;4-dihydro-l3234 triazol-3-one, 2-(4-amino-3-methyl-benzyl)-4-(2-chloro-phenyl)-234-dihydro-l,234-triazoi-3-one3 2-(4-arnino-3-methyl-benzyl)-4-(4-trifl 2-(4-airidno-3-methyl-benzyl)-5-methyl-4-(4-trifluoromethyj-phenyl)-234-dihyd2-(4-amino-3-methyl-benzyl)-4-(2-cUoro-phenyl)-5-methylsulfanyl-2J4-dihydro-lf2,4-triazol-3-one3 2-(4-amino-3-methyl-benzyl)-5-methylsulfanyl-4-(4-trifluoromethyl-phenyl)-234-dihydro-l32,4-triazol-3-one, l-(4-amiao-3-methyl-benzyl)-4-methyl-l34-dihydro-tetrazol-5-one3 l -(4-amino-3 -methyl-benzyl)-4-ethyl-134-dihydro-tetrazol-5-one, l-(4-amino-3-methyl-benzyl)-4-propyl-l34-dihydro-tetrazol-5-one3 l -(4-amino-3-methyl-benzyl)-4-isobu1yl-1,4-düiydro-tetrazol-5-one3 l -(4-amino-3-methyl-benzyl)-4-(232,2-trifluoro-ethyl)-134-dihydro-tetrazoI-5-one3 l-(4-amino-3-methyl-benzyl)-4-(4,434-trifluoro-butyl)-l,4-düiydro-tetrazol-5-one3 l-(4-ämino-3-methyl-benzyl)-4-(33333-trichloro-2-methyl-propyl)-l34-dihydro-tetrazol-5-one3 l-(4-arnino-3-metihiyl-benzyl)-4-cyclopropyl-l34-dihydro-tetrazol-5-one3 l -(4-amino-3 -methyl-benzyl)-4-cyclohexyl-1,4-düiydro-tetrazol-5-one5 l-(4-amino-3-methyl-benzyl)-4-phenyl-l34-dihydro-tetrazol-5-one3 l -(4-amino-3-methyl-benzyl)-4-(2-fluoro-phenyl)-1,4-diliydro-tetrazol-5-one, l -(4-amino-benzyl)-4-(2-chloro-phenyl)-134-dihydro-tetrazol-5-one, l-(4-amino-3-methyl-benzyl)-4-(2-chloro-phenyl)-l34-dihydro-tetrazol-5-one3 l-[l-(4-amino-3-methyl-phenyl)-ethyl]-4-(2-chloro-pb.enyl)-l34-dib.ydro-tetrazol-5-one, l -(4-amino-3-metliyl-benzyl)-4-(2-methyl-phenyl)-134-dihydro-tetrazol-5-one, l -(4-amino-3-meth.yl-benzyl)-4-(2-methoxy-phenyl)-1,4-dihydro-tetrazol-5-one3 l -(4-amino-3-methyl-benzyl)-4-(2-trifluoroinetiiyl-phenyl)-134-dihydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyl)-4-(2-trifluoromethoxy-phenyl)-l34-dib.ydro-tetrazol-5-one., l-(4-amino-3-methyl-benzyl)-4-(3-fluoro-phenyl)-l34-dihydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyI)-4-(3-chloro-phenyl)-l34-dihydro-tetrazol-5-one3 l -(4-amino-3-methyl-benzyl)-4-(3 -methyl-phenyl)-134-dihydro-tetrazol-5-one., l-(4-amino-benzyl)-4-(3-trifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one3 l -(4-amino-3-methyl-benzyl)-4-(3 -trifluoromethyl-phenyl)-134-dihydro-tetrazol-5-one., l-(4-amino-3-meth.yl-benzyl)-4-(3-difluorometlioxy-phenyl)-l34-dihydro-tetrazol-5-one., l-(4-amino-3-methyl-benzyl)-4-(3-1iifluoromethoxy-phenyl)-l]4-diliydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyl)-4-(4-fluoro-phenyl)-l34-dihydro-tetrazol-5-one, l-(4-amino-3-methyl-benzyl)-4-(4-chloro-phenyl)-l,4-dihydro-tetrazol-5-one3 l -(4-amino-3 -methyl-benzyl)-4-(4-bromo-phenyl)-1,4-dihydro-tetrazol-5 -one, l-(4-amino-3-meth}4-benzyl)-4-(4-methyl-phenyl)-lJ4-dihydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyl)-4-(4-isopropyl-phenyl)-l;4-dihydro-tetrazol-5-one3 l-(4-amino-benzyl4)-4-(4-trifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one3 l-(4-amino-2-chloro-benzyl)-4-(4-trifluorornethyl-phenyl)-l34-dthydro-tetrazol-5-one3 „ l-(4-amino-3-cliloro-benz3'l)-4-(4-1rifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one, l-(4-amino-3-methyl-benzyl)-4-(4-trifluoromethyl-phenyl)-lJ4-dihydro-tetrazol-5-one3 l -(4-atnino-3 -methyl-benzyl)-4-(4-difluoromethoxy-pb.enyl)-134-dihydro-tetrazol-5 -one, l-(4-aniino-3-methyl-beii254)-4-(4-trifluoromethoxy-phenyl)-l,4-dihydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyl)-4-(4-trifluorome1žiylsulfanyl-phenyl)-l34-dihydro-tetrazol-5-one3 l-(4-amino-3-me1hyl-benzyl)-4-(4'-trifluoroinethyl-biphenyl-4-yl)-l34-dihydro-tetrazol-5-one3 l-(4-amino-3-me1žiyl-benzyl)-4-(3,5'-bis-trifluoromethyl-biphenyl-4-yl)-l34-dib.ydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyl)-4-(4-bromo-2-fluoro-phenyl)-l.,4-dihydro-tetrazol-5-one3 !-(4-amiiio-3-methyl-benzyl)-4-(2-fluoro-3-1rifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one., l -(4-amino-3-methyl-benzyl)-4-(3-bromo-4-trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one3 l-(4-amino-3-meth.yl-benzjd)-4-(3-chloro-4-trifluoromethoxy-phenyl)-lJ4-dihydro-tetrazol-5-one3 l-(4-ainino-3-methyl-benzyl-4-(4-fluoro-3-trifluoromethyl-phenyl)-l,4-dihydro-tetrazol- !-(4-amino-3-methyl-beri2yl)-4-(2-fluoro-5-trifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-oneJ l -(4-ammo-3-methyl-benzyl)-4-(4-chloro-3-trifluorometliyl-phenyl)-1,4-dihydro-tetrazol-5-orie, l-(4-amino-3-methyl-benzyl)-4-(334-dicliloro-phenyl)-l34-diliydro-tetrazol-5-one., l -(4-amino-3-meth.yl-benzyl)-4-(3,4-bis-trifluoromethyl-phenyl)-1,4-düiydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyl)-4-(3-fluoro-5-trifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyl)-4-(335-dicHoro-phenyl)-l)4-dili)'dro-tetrazol-5-one3 l -(4-amino-3-methyl-benzyl)-4-(3,5-dimethoxy-phenyl)-1,4-dihydro-tetrazol-5-one3 l-(4-armno-2-chloro-benzyl)-4-(3,5-bis-trifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one, l-(4-amino-3-chloro-benzyl)-4-(335-bis-trifluorometh)d'-phenyl)-l34-dihydro-tetrazol-5-one, l-(4-amino-3-methyl-benzyl)-4-(335-bis-trifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one3 l -(4-amino-2-methoxy-benzyl)-4-(3,5-bis-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5 -one, l-(4-amino-3-methoxy-benzyl)-4-(335-bis-trifluoromethyl-phenyl)-l,4-dihydro-tetrazol-5-one, l -(4-amino-3,5 -dimethyl-benzyl)-4-(3,5-bis-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one, l-[l-(4-ammo-3-meihyl-phenyl)-eÜiyl]-4- l-(4-amino-3-methyl-benzyl)-4-(3-chloro-2-methoxy-5-inethyl-phenyl)-l,4-dihydro-tetrazol-5-one, l-(4-amino-3-methyl-benzyl)-4-(2,2-difluoro-benzo[l.,3]dioxol-5-yl)-l,4-dihydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyl)-4-(2,2333-tetrafluoro-2,3-dihydro-benzo[l)4]dioxin-6-yl)-l.,4-diliydro-tetrazol-5-one, l-(4-ammo-3-me%l-benzyl)-4-(2,233-1rifluoro-2)3-dihydro-benzo[l)4]cHoxin-6-yl)-l34-dihydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyl)-4-(2,33-trifluoro-2,3-dihydro-benzo[l54]dioxin-6-yl)-l,4-dihydro-tetrazol-5-one, l-(4-amino-3-methyl-benzyl)-4-(22,33337-pentafluoro-233-dihydro-benzo[l,4]dioxin-6-yl)-l34- dihydro-tetrazol-5-one, l -(4-amino-3 -methyl-benzyl)-4-(3,5 -dichloro-2,6-diethyl-phenyl)-134-dihydro-tetrazol-5-one3 l-(4-amino-3-methyI-benzyl)-4-benzyl-l)4-dihydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyl)-4-(4-fluoro-benzyl)-l34-dihydro-tetrazol-5-one., l -(4-amino-3 -methyl-benzyl)-4-(4-chloro-phenyl)-1,4-dihydro-tetrazol-5-one3 l-(4-anüno-3-methyl-benzyl)-4-(4-trifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one, l-(4-amino-3-rnethyl-benzyl)-4-[l-(2-fluoro-phenyl)ethyl]-l,4-dihydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyl)-4-[l-(2-chloro-phenyl)ethyl]-l34-dihydro-tetrazol-5-one, l-(4-amino-3-methyl-benzyl)-4-[l-(2-trifluoromethyl-phenyl)-ethylJ-l,4-dihydro-tetrazol-5-one; l-(4-aniino-3-methyl-benzyl)-4-l-[l-(3-fluoro-phenyl)-ethyl]-l34-dihydro-tetrazol-5-one) l-(4-amino-3-methyl-benzyl)-4-[l-(3-chloro-phenyl)-ethyl]-l34-dihydro-tetrazol-5-one3 l -(4-amino-3-mefhyl-benzyl)-4- [ l -(3 -frifluoromethyl-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one, l-(4-amino-3-methyl-benzyl)-4-[l-(4-fluoro-phenyl)-ethyl]-l,4-dihydro-tetrazol-5-one, l-(4-amino-3-met:hyl-benzyl)-4-[l-(4-chloro-phenyl)-ethyl]-l34-dihydro-tetrazol-5-oneJ l-(4-amino-3-methyl-benq4)-4-[l-(4-1rifluorometh}'l-phen3'l)-ethyl]-l,4-dihydro-tetrasol- l-(4-amino-3-methyl-benzyl)-4-[l-(234-difluoro-phenyl)-eÜiyl]-l,4-dihydro-tetrazol-5-one3 l -(4-amino-3-methyl-benzyl)-4-[l -(2,4-dichloro-phenyl)-ethyl]-134-dib.ydro-tetrazol-5-one, l -(4-amino-3 -methyl-benzyl)-4- [ l -(3,4-diflu6ro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one. The compounds of the formula (JV), staiting materials in the above-mentioned preparation process (b), are novel ones and can be easily obtained according to the process described in JP-A 61- 246161, for example, by reacting a compound represented by the formula- (Figure Removed)wherein X and n have the same definition as aforementioned, with the compounds of the aforementioned formula (TS) (Figure Removed) in which R represents a hydrogen atom and Y, m, A1, r, Q, A2, s and E have the same definitions as aforementioned. The reaction can be conducted in an adequate diluent. As examples of the diluent used in that case there can be mentioned aliphatic, alicyclic and aromatic hydrocarbons (may be optionally chlori-nated), for example, pentane, hexane, cyclohexane, petroleum ether, hgroine, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, di-chlorobenzene; ethers, for example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tefrahydrofuran (THF), diethylene glycol dimethyl ether (DGM); esters, for example, ethyl acetate, amyl acetate; acid amides, for example, dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone, l,3-dimethyl-2-imidazolidinone, hexamethyl phosphoric triamide (HMPA); acids, for example, acetic acid. The reaction can be conducted in a substantially wide range of temperature. It can be conducted at the temperatures in a range of generally room temperature to. about 200°C, preferably room temperature to 150°C. Although said reaction is conducted desirably under normal pressure, it can be operated also under elevated pressure or under reduced pressure. In conducting the reaction, the aimed compounds can be obtained, for example, by reacting equimolar amount or a litile excess amount of the compounds of the formula (EH) to l mole of the compounds of the formula (X) in a diluent, for example, acetic acid. Many of the compounds of the above-mentioned formula (X) are known (available on the marker) compounds and as their specific examples there can be mentioned, phthalic anhydride, 3-fluorophthalic anhydride, 3-chlorophthalic anhydride, 3-bromophthalic anhydride, 3-iodophthalic anhydride, 3-methylphthalic anhydride, 3-nitrophthalic anhydride, 3,6-difluorophthalic anhydride, 3,6-dichlorophthalic anhydride, 4,5-dichlorophthalic anhydride, 3,4,5,6-tetrafluorophthalic anhydride, 3,4,5,6-tetrachlorophthalic anhydride, 3-methanesulfonyloxyphthalic anhydride. Among the above-mentioned examples, 3-methanesulfonyloxyphthalic anhydride can be easily obtained from 3-hydroxyphthalic anhydride and methanesulfonyl chloride according to the process described in Tetrahedron Lett., 1988, 29, 5595-5598. Similarly the compounds of the aforementioned formula (JU), in which R3 represents a hydrogen atom, starting materials for the compounds of the formula (IV), can be easily obtained, as described in the aforementioned preparation process (a), by a catalytic hydrogen reduction of the compounds represented by the aforementioned formula (IX) häving a nitro group in place of an amino group, corresponding to the amino group (R3 ='H) in the formula (UI). The catalytic hydrogen reduction can be conducted in an adequate diluent and as examples of the diluent used in that case there can be mentioned ethers, for example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, tetrahydrofuran (THF); alcohols, for example, methanol, etha-nol, isopropanol, butanol, ethylene glycol, and as catalytic reduction catalyst there can be mentioned palladium carbon, Raney nickel, platinum oxide. It can be conducted at the temperatures generally between about O to about 100°C, preferably room temperature to about 80°C. Said reaction can be operated under normal pressure to elevated pressure. For example, an objective compound of the formula (UI), in which R3 represents hydrogen, can be obtained by hydrogenation of l mole of the nitro compound in a diluent, for example, ethanol in the presence of 0.1-10 % (w/w) palladium carbon. Moreover, the compounds of the formula (IH), in which R3 represents hydrogen, can also be obtained by a reaction with a metal ete. instead of a catalytic hydrogen reduction. As a process using a metal ete. there can be mentioned, for example, a process of treating iron powder in acetic acid, a process of reacting zinc dust under the neutral condition (Organic Syntheses Collective Vol. E, p. 447), a process of reacting stannic chloride under an acidic condition (Organic Syntheses Collective Vol. H, p. 254), a process of reacting titanium trichloride under the neutral condition, ete. As specific examples of the compounds of the formula (III), in which R3 represents a hydrogen atom, there can be mentioned, for example, l-(4-amino-3-methyl-benzyl)-lH-pyrazole, l-(4-amino-3-rnethyl-benzyl)-3-methyl-lH-pyrazole, l-(4-amino-3-methyl-benzyl)-4-methyl-lH-pyrazole, l-(4-amino-3-niethyl-benzyl)-4,5-dichloro-lH-imidazole, l-(4-amino-3-methyl-benzyl)-lH-l,253-triazole, l -(4-amino-3-methyl-benzyl)- IH-1,2,4-triazole, l-(4-amino-3-methyl-benzyl)-lH-tetrazole, . l-(4-arnino-3-rnethyl-benz3'l)-5-methyl-lH-te1razoleJ l-(4-amino-3-methyl-benzyl)-5-(2-chloro-phenyl)-lH-tetrazole, l -(4-amino-3 -methyl-benzyl)-5 -(3-trifluoromethyl-phenyl)- IH-tetrazole, % l-(4-amino-3-rnethyl-benzyl)-5-(4-trifluorornethyl-phenyl)-lH-tetrazole., l-(4-arm'no-3-]jiethyl-benzyl)-5-(3,5-bis-trifluoromethyl-phenyl)-lH-tetrazole, l -(4-amino-3 -meth)d-benzyl)-5 -(3 -trifluoromethoxy-phenyl)-1 H-tetrazole, l-(4-arrmo-3-methyl-benzyl)-3-(4-trifluoromethyl-phenyl)-imidazolydm-2-oneJ l-(4-ammo-3-methyl-benzyl)-3-(4-1rifluorome1hyl-phenyl)-l,3-dihydro- l -(4-amino-3 -methyl-benzyl)-3 -(4-trifluoromethyl-phenyl)-irtiidazolydin-2,4-dione, !-(4-arrmo-3-me1hyl-benzyl)-3-(4-1iifluorometia}d-phen34)-imidazolydm-2,4J5-1rione., l-(4-amino-3-rnethyl-benzyl)-3-(4-trifluoromethyl-phenyl)-lH-pyrazole, 4-(4-amino-3 -methyl-benzyl)-2-(2-fluoro-phenyl)-2.,4-dihydro-1,2,4-triazol-3 -one, 4-(4-amino-3-methyl-benzyl)-2-(2-chloro-phenyl)-2,4-dihydro-l,2J4-triazol-3-oneJ 4-(4-amino-3-niethyl-benzyl)-2-(2-1rifluoromethyl-phenyl)-234-dihydro-l,2,4-triazol-3-one, 4-(4-arniiio-3-methyl-benzyl)-2-(3-fluoro-phenyl)-2,4-dihydro-l,2,4-triazol-3-one, 4-(4-amino-3-methyl-benzyl)-2-(3-chloro-phenyl)-2,4-diliydro-l,2J4-triazol-3-one,- 4-(4-amino-3-memyl-beri2yl)-2-(3-trifluorometliyl-phenyl)-2,4-düiydro-l,2,4-tiiazol-3-oneJ 2-(4-fluoro-phenyl)-4-(4-amino-3-methyl-benzyl)-2,4-dihydro-l,2,4-triazol-3-one, 4-(4-anTino-3-rnethyl-benzyl)-2-(4-chloro-phenyl)-2,4-dihydro-l,2.,4-triazol-3-one, 4-(4-anoino-3-methyl-benzyl)-2-(4-1rifiuoromethyl-phenyl)-234-dihydro-l,2,4-triazol-3-one, 4-(4-amino-3 -methyl-benzyl)-2-(3,4-bis-trifluoromethyl-phenyl)-234-dihydro-1,234-triazol-3 -one, 4-(4-ammo-3-methyl-beri2yl)-2-(335-bis-trifluoromethyl-phenyl)-2,4-dmydro-l,2J4-1iiazol-3-on 4-(4-amrno-3-methyl-benzyl)-5-1rifluorome triazol-3-one., 2-(4-ammo-3-rnethyl-benzyl)-4-(2-chloro-phenyl)-2J4-dihydro-l,2,4-triazol-3-oiie3 2-(4-aiimo-3-methyl-benzyl-4- 2-(4-amino-3-me1hyl4)enzyl)-5-methyl-4-(4-tr 2-(4-amino-3 -methyl-benzyl)-4-(2-chloro-phenyl)-5 -methylsulfanyl-234-dihydro-132,4-triazol-3-one3 2-(4-amino-3-methyl-benzyl-5-methylsulfanyl-4 triazol-3-one, l-(4-amino-3-methyl-beri2yl)-4-methyl-lJ4-dihydro-tetrazol-5-oneJ l -(4-amino-3-methyl-benzyl)-4-ethyl-1,4-dihydro-tetrazol-S-one, l -(4-amino-3-methyl-benzyl)-4-propyl-1,4-dihydro-tetrazol-5-one, l -(4-amino-3-methyl-benzyl)-4-isobutyl-1,4-dihydro-tetrazol-5 -one, l -(4-amino-3-methyl-benzyl)-4-(2,2,2-trifluoro-ethyl)-134-dihydro-tetrazol-5-one3 l-(4-amino-3-methyl-benz3'l)-4-(4J4,4-trifluoro-butyl)-lJ4-diliydro-tetrazol-5-one, l-(4-amino-3-methyl-benzyl)-4-(3,3,3-trich]oro-2-methyl-propyl)-l)4-dihydro-tetrazol-5-one, l -(4-amino-3-methyl-benzyl)-4-cyclopropyl-1,4-dihydro-tetrazol-S-one.," l -(4-amino-3-methyl-benzyl)-4-cyclohexyl-1,4-dihydro-tetrazol-5-one, l -(4-amino-3-methyl-benzyl)-4-phenyl-1,4-dihydro-tetrazoI-5-one,, l-(4-amino-3-methyl-benzyl)-4-(2-fluoro-phenyl)-l,4-dihydro-tetrazol-5-onea l -(4-amino-benzyl)-4-(2-cMoro-phenyl)-1,4-dihydro-tetrazol-5-one., l -(4-aminp-3-methyl-benzyl)-4-(2-chloro-phenyl)-1-dihydro-tetrazol-S-one, l-[l-(4-ariiino-3-methyl-phenyl)-ethyl]-4-(2-cliloro-phenyl)-lJ4-dihydro-tetrazol-5-one3 l-(4-anaino-3-methyl-benzyl)-4-(2-methyl-phenyl)-l,4-dihydro-tetrazol-5-one., l-(4-amino-3-methyl-berizyl)-4-(2-methoxy-phenyl)-l34-dihydro-tetrazol-5-one3 l -(4-amino-3-methyl-benzyl)-4-(2-trifluorome1;hyl-phenyl)-1,4-dihydro-tetrazol-5-one., l-(4-amino-3-methyl-benzyl)-4-(2-1rifluoromethoxy-phenyl)-l34-diliydro-tetrazol-5- one, l-(4-amino-3-metliyI-benzyl)-4-(3-fluoro-phenyl)-l34-diliydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyl)-4-(3-chloro-phenyl)-l34-dihydro-tetrazol-5-one, l-(4-amino-3-meth3d-benzyl)-4-(3-methyl-phenyl)-l34-dihydro-tetrazol-5-one3 l-(4-aniino-benzyl)-4-(3-trifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyl)-4-(3-trifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyl)-4-(3-difluoromethoxy-phenyl)-l34-dihydro-tetrazol-5-one3 l -(4-amino-3 -methyl-benzyl)-4-(3 -trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5- one, l-(4-amino-3-methyl-benzyl)-4-(4-fiuoro-phenyl)-l34-dihydro-tetrazol-5-one3 l-(4-aniino-3-methyl-benzyl)-4-(4-cMoro-phenyl)-l,4-dihydro-tetrazol-5-one, l-(4-amino-3-methyl-benzyl)-4-(4-bromo-phenyl)-l34-dihydro-tetrazol-5-one3 l -(4-amino-3 -methyl-benzyl)-4-(4-methyl-phenyl)-1,4-dihy dro-tetrazol-5-one, l -(4-amino-3-methyl-benzyl)-4-(4-isopropyl-phenyl)-1,4-dihydro-tetrazoI-5-one3 l -(4-amino-benzyl)-4-(4-trifluoromethyl-phenyl)-134-dih.ydro-tetrazol-5-one3 l -(4-amino-2-chloro-benzyl)-4-(4-trifluoromethyl-phenyl)-134-dihydro-tetrazol-5-one3 l -(4-amino-3-chloro-benzyl)-4-(4-trifl'uorornethyl-phenyl)-1,4-dihydro-tetrazol-5-one, l -(4-amino-3-methyl-berizyl)-4-(4-trifluoromethyl-phenyl)-1 ,4-dihydro-tetrazol-5-one., l-(4-amino-3-methyl-benzy1)-4-(4-difluoromethoxy-phenyl)-l,4-dihydro-tetrazol-5-oneJ l-(4-amino-3-methyl-benzyl)-4-(4-trifluoromethoxy-phenyl)-lJ4-dihydro-tetrazol-5- one, l -(4-amino-3-methyl-benzyl)-4-(4-trifLuoromethylsulfanyl-phenyl)-1 34-dihydro-tetrazol-5-one3 l -(4-amino-3-methyl-benzyl)-4-(4' -trifluoromethyl-biphenyl-4-yl)-134-dihydro-tetrazol-5-one, l -(4-aminq-3-methyl-benzyl)-4-(3' ,5 '-bis-trifluoromethyl-biphenyl-4-yl)-1,4-dihydro-tetrazol-5-one, l -(4-amino-3-methyl-benzyl)-4-(4-bromo-2-fluoro-phenyl)-1 ,4-dihydro-tetrazol-5-one3 l -(4-amino-3-methyl-benzyl)-4-(2-fluoro-3 -trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one; l-(4-amino-3-methyl-benzyl)-4-(3-bromo-4-trifluoromethoxy-phenyl)-l,4-dihydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyl) -(3-cUoro-4-trifluorome1hoxy-phenyl)-l,4-dihydro-tetrazol-5-on l-(4-amino-3-methyl-benzyl) -(4-fluoro-3-trifluoromethyl-phenyl)-lJ4-dih.ydro-tetrazol-5-one5 l-(4-amino-3-methyl-benzyl)-4-(2-fluoro-5-trifluoromethyl-phenyl)-l)4-dihydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyl)-4-(4-chloro-3-1rifluoromethyl-phenyl)-l,4-dihydro-tetrazol-5-one) l-(4-aniino-3-methyl-beaxzyl)-4-(3,4-dichloro-phenyl)-l,4-diliydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyl)-4-(3,4-bis-l-(4-amino-3-methyl-benzyl)-4-(3-fluoro-5-trifluoromethyl-phenyl)-l,4-dihydro-te1razol-5-one3 l -(4-amino-3 -methyl-benzyl)-4-(3 35-dichlorõ-phenyl)-134-dihydro-tetrazol-5 -one, l-(4-amino-3-methyl-benzyl)-4-(335-diriiethoxy-pb.enyl)-l34-dihydro-tetrazol-5-one3 l-(4-amino-2-cUoro-benzyl)-4-(3,5-bis-trifluoromethyl-phenyl)-l.,4-dihydro-tetrazol-5-one3 l-(4-amino-3-cKloro-benzyl)-4-(335-bis-1iifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one3 l -(4-amino-3 -methyl-benzyl)-4-(3,5-bis-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one, !-(4-animo-2-me1hoxy-benzyl)-4-(3,5-bis-trifluoromethyl-phenyl)-l34-dih)'dro-tetrazol-5-one3 l -(4-amino-3-methoxy-benz)4)-4-(3,5-bis-trifluoromethyl-phenyl)-1 -dihydro-tetrazol-S-one, l -(4-amino-3,5-dimethyI-benzyl)-4-(3,5-bis-triiluoromethyl-phenyl)-1 -dihydro-tetrazol-S-one, l -[ l -(4-amino-3-methyl-phenyl)-ethyl]-4-(3,5-bis-trifluoromethyl-phenyl)-1 -dihydro-tetrazol-S-one, l-(4-amino-3-me&yl-benzyl)-4-(3-cbJoro-2-me.thoxy-5-niethyl-phenyl)-lJ4-dihydro-tetrazol-5-one5 l-(4-amino-3-methyl-bejQzyl)-4-(2,2-difluoro-benzo[lJ3]dioxol-5-yl)-l,4-dihydro-tetrazol-5-one, l -(4-amino-3-methyl-benzyl)-4-(2,2,3?3-tetrafluoro-2,3-dihydro-benzo[l ,4]dioxin-6-yl)-1,4-dihydro- tetrazol-5-one, l-(4-ainino-3-methyl-benzyl)-4-(2,2J3-1rifluoro-2)3-dihydro-benzo[l,4]dioxin-6-yl)-l)4-dihydro- tetrazol-5-one, l -(4-amino-3-naethyl-benzyl)-4-(2,3,3-trifluoro-2)3-dihydro-benzo[l ,4]dioxin-6-yl)-1,4-dihydro- tetrazol-5-one, l-(4-amino-3-methyl-benzyl)-4-(232]3,3,7-pentafluoro-233-diliydro-benzo[l34]dioxin-6-yl)-l34- dihydro-tetrazol-5-one, l -(4-amino-3 -methyl-benzyl)-4-(3,5 -dichloro-2,6-diethyl-phenyl)-1,4-dib.ydro-tetrazol-5-one, 1 -(4-amino-3 -methyl-benzyl)-4-benzyl- 1 ,4-dihydro-tetrazol-5-one, l -(4-amino-3 -mefhyl-benzyl)-4-(4-fluoro-benzyl)- 1 ,4-dihydro-tetrazol-5-one, l -(4-amino-3-methyl-benzyl)-4-(4-chloro-phenyl)- 1 ,4-dihydro-tetrazol-5-one, l-(4-amino-3-methyl-benzyl)-4-(4-trifluoromethyl-phenyl)-l,4-dihydro-tetrazol-5-one, l-(4-amino-3-methyl-benzyl)-4-[l-(2-fluoro-phenyl)efhyl]-l)4-dihydro-tetrazol-5-one) l -(4-amino-3-methyl-benzyl)-4-[l -(2-chloro-phenyl)-ethyl]- 1 ,4-dihydro-tetrazol-5-one, l-(4-amino-3-methyl-benzyl-[l-(2-trifluoromethyl-phenyl)-ethyl]-l,4-dihydro-tetrazol-5-one) l-(4-amino-3-methyl-benzyl)-4--l-[l-(3-fluoro-phenyl)-ethyl]-l)4-dihydro-tet:azol-5-oneJ l-(4-amino-3-methyl-benzyl)-4-[l-(3-cbloro-phenyl)-ethyl]-l.,4-diliydrõ-tetrazol-5-one, l-(4-arnmo-3-memyl-benzyl)-4-[l-(3-trifl l-(4-ainirLO-3-methyl-berizyl)-4-[l-(4-£Iuoro-pheny])-e1iiyl]-l,4-dihydro-tetrazol-5-oneJ l -(4-amino-3-methyl-benzyl)-4- [ l -(4-chloro-phenyl)-ethylj- 1 ,4-dihy dro-tetrazol-5-one, l -(4-amino-3-methyl-benzyl)-4-[ l -(4-trifluoromethyl-phenyl)-ethyl]-l ,4-dihydro-tetrazol-5-one, l -(4-ammo-3-methyl-benzyl)-4-[ l -(2,4-difluoro-phenyl)-ethyl]- 1 ,4-dihydro-tetrazol-5-one, l-(4-amino-3-methyl-benzyl)-4-[l-(2)4-dichloro-phenyl)-ethyl]-l,4-dihydro-tetrazol-5-one, l-(4-aminb-3-methyl-benzyl)-4-[l-(3;4-difluoro-phenyl)--ethyl]-l.,4-dih3'dro-tetrazol-5-one. The compounds of the above-mentioned formula (IX) are novel compoxinds and can be obtained, for example, by reacting compounds of the formula (Figure Removed)wherein Y, m, A1 and r have me same defmition as aforementioned and M represents chloro, bromo or methylsulfonyloxy, and compounds of the formula wherein Q, A2, s and E have tlae same definition as aforementioned. The compounds of the above-mentioned formula (XI) are compounds well knov m in the field of organic chemistry (cf. Chem. Abstr. 1963, 55, 3444e; Bull Soe. Chim. Fr. 1934, 539-545; J. Chem. Res. Mmiprint, 1987, 8, 2133-2139; J. Chem. Soe. B 1967, 1154-1158; J, Chem. Soe. 1961, 221-222; J. Amer. Chem. Soe. 1989, 111, 5880-5886). Specifically there can be mentioned as examples 4-nitrobenzyl chloride, (available on the market) 4-bromobenzyl chloride, (available on the market) 2-chloro-4-mtrobenzyl chloride, 2-methyl-4-nitrobenzyl chloride, 2-memoxy-4-nitrobenzyl chloride, 3-chloro-4-nitrobenzyl chloride, 3-memyl-4~nitrobenzyl chloride, 3-methoxy-4-nitrobenzyl chloride, 4-nitrobenzyl methanesulfonate, 2-cUoro-4-mtrobeiizyl methanesulfonate, 2-methyl-4-nitrobenzyl methanesulfonate, 2-methoxy-4-nitrobenzyl methanesulfonate, 3-chloro'-4-nitrobenzyl methanesulfonate, 3 -methyl-4-nitrobenzyl methanesulfonate, 3-methoxy-4-nitrobenzyl methanesulfonate, l -(3-chloro-4-nitxo-phenyl)-ethyl methanesulfonate, l -(3-methyl-4-nitro-phenyl)-ethyl methanesulfonate, l-(3-methoxy-4-nitro-phenyl)-ethyl methanesulfonate. The nitro-substituted benzoic acids and their esters, starting materials for the compounds of the formula (XI) are kno\vn from the literature (cf., for example, Chem. Ber. 1919, 52, 1083; Bull. Soe. Chim. Fr. 1962,2255-2261; Tetrahedron 1985, 115-118; Chem. Pharm. Bull, 1993, 41, 894-906). The compounds of the above-mentioned formula (Xn) include known compounds and as their specific examples there can be mentioned, IH-pyrrole, 3 -methyl- IH-pyrrole, 2,5-dimethyl-lH-pyrrole, IH-pyrazole, 3 -methyl-1 H-pyrazole, 4-methyl- IH-pyrazole, 4-chloro-lH-pyrazole, 3,5-dimethyl-lH-pyrazole, IH-imidazole, 4-methyl- IH-imidazole, 4,5-dichlqro-lH-imidazole, lH-[lA3]-triazole, lH-[l,2,4]-triazole, IH-tetrazole, 5-metyl-lH-tetrazole, 5 -phenyl- IH-tetrazole, 5-(2-chloro-plien)'l)- IH-tetrazole, 5-(4-chloro-phenyl)- IH-tetrazole, 5-(3-trifluoromethyl-phenyl)-lH-tetrazole3 5-(4-trifluoromethyl-phenyl)-lH-tetrazole, 5-(3,5-bis-trifluoromethyl-phenyl)- IH-tetrazole, 5-(3-trifluoromethoxy-phenyl)-lH-tetrazole, succinimide., l-(4-trifluoromethyl-phenyl)-imidazolidin-2-one l -(4-trifluoromethyl-phenyl)-1,3 -dihydro-imidazol-2-one, 3-(4-trifluoromethyl-phenyl)-imidazolidin-2,4-dione 2-(2-chloro-phenyl)-2,4-dihydro-[l32,4]triazol-3-ohe, 2-(2-trifluoromethyl-phenyl)-2,4-dihydro-[ l ,2,4]triazol-3-one, 2-(3-fluoro-pheayl)-2,4-dihydro-[l,2,4]tri-azol-3-one, 2-(3-chloro-phenyl)-2,4-dihydro-[l,2,4]triazol-3-one, 2-(3-trifluoromethyl-phenyl)-2,4-dihydro-[l,2J4]triazol-3-one, 'v* 2-(4-fluoro-phenyl)-2,4-dihydro-[l,2,4]triazol-3-one, 2-(4-chloro-phenyl)-2)4-dih}'dro-[l)2,4]triazol-3-one, 2-(4-trifluoromethyl-phenyl)-254-dihydro-[l,2,4]triazol-3-oiie3 2-(3,4-bis-trifIuoromeäiyl-phenyl)-2.,4-dihydro-[l,234]triazol-3-one, 2-(3,5-bis-trifluoromethyl-phenyl)-2,4-dihydro-[ l ,234]triazol-3-one, 5-trifluoromethyl-2-(4-trifluorometh.yl-phenyl)-234-dihydro-[l3234]triazol-3-one, 4-(2-chIoro-phenyl)-2,4-dihydro-[l3234]triazol-3-one3 4-(4-trifluoromethyl-phenyl)-234-dih.ydro-[ l ,234]triazol-3 -one, 5-methyl-4-(4-trifluoromethyl-phenyl)-234-düiydro- [ l ,234Jtriazol-3 -one, 4-(2-chloro-phenyl)-5-methylsulfanyl-2,4-dihydro-[l3234]triazol-3-one, 5-meth}'lsulfanyl-4-(4-trifluoromethyl-phenyl)-2)4-dihydro-[l32,4]triazol-3-one3 l -methyl-134-dihydi-o-tetrazol-5-one3 l -ethyl-1,4-dihydro-tetrazol-S-one, l-propyl-l,4-dihydro-tetrazol-5-one, l-isobutyl-l34-dihydro-tetrazol-5-one, l -(2,2,2-trifluoro-eÜiyl)-134-dihydro-tetrazol-5-oiae; l -(4,4,4-trifluoro-butyl)-1 dihydro-tetrazol-S-one, l-(3,3,3-trichloro-2-methyl-propyl)-134-dihydro-tetrazol-5-one3 l -cyclopropyl-1,4-düiydro-tetrazol-5-one, l-cyclohexyl-l34-dihydro-tetrazol-5-one3 l-phenyl-l34-dihydro-tetrazol-5-one3 l-(2-fluoro-phenyl)-l34-dihydro-tetrazol-5-one3 1 -(2-chloro-phenyl)-l ,4-dihydro-tetrazol-5-one, l -(2-methyl-phenyl)-1,4-dihydro-tetrazol-5 -one, l -(2-methoxy-phenyl)-1 ,4-dihydro-tetrazol-5-one, l-(2-trifluoromethyl-phenyl)-l,4-dihy(iro-tetrazol-5-one, l-(2-trifluoromethoxy-phenyl)-lJ4-dihydro-tetrazol-5-one, . l -(3 -fluoro-phenyl)-1,4-dihydro-tetrazol-5 -one, l -(3 -cliloro-phenyl)-1,4-dihydro-tetrazol-5-one, l-(3 -methyl-phenyl)-1,4-dihydro-tetrazol-5 -one, l -(3 -trifluoromethyl-phenyl)-1.,4-dihy dro-tetrazol-5 -one, l-(3-difluorometiioxy-phenyl)-l54-dihydro-tetrazol-5-one, l -(3 -trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one, l -(4-fluoro-phenyl)-1,4-dihydro-tetrazol-5 -one, l-(4-chloro-phenyl)-l,4-dihydro-tetrazol-5-one, l-(4-bromo-phenyl)-l,4~dihydro-tetrazol-5-one, l-(4-methyl-phenyl)-l,4-diliydro-tetra2ol-5-one, l-(4-isopropyl-phenyl)-l,4-düiydro-tetrazol-5-one, l -(4-trifluorometii)'l-phenyl)-1,4-diliydro-tetrazol-5 -one, l-(4-difluorometho7cy-phenyl)-l,4-dihydro-tetrazol-5-one3 l-(4-trifluoromethoxy-phenyl)-l,4-dihydro-tetrazol-5-one, l -(4-trifluorometiaylsulfanyl-phenyl)-1,4-dihy dro-tetrazol-5 -one, l -(4' -trifluoromethyl-biphenyl-4-yl)-1,4-dihydro-tetrazol-5-one, l -(3' ,5' -bis-trifluoromethyl-biphenyl-4-yl)-1,4-dihydro-tetra2ol-5-one, l -(4-bromo-2-iluoro-phenyl)-1,4-düiydro-tetrazol-5-one, l -(2-fluoro-3 -trifluorometh}'l-phenyl)-1,4-dih.ydro-tetrazol-5-one, l-(3-bromo-4-trifluoromethoxy-phenyl)-l,4-dihydro-tetrazol-5-one, l-(3-chloro-4-trifluoromet:hoxy-phenyl)-l,4-dihydro-te1razol-5-one, l -(4-fluoro-3-trifluoromefhyl-phenyl)-1,4-dihydro-tetrazol-5-one, l-(2-fiuoro-5-trifluoroniethyl-phenyl)-l,4-dihydro-tetrazol-5-one, l -(4-chloro-3 -trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one, l -(3 54-dichloro-phenyl)-1,4-dihydro-tetrazol-5-one, l -(3,4-dichloro-phenyl)-1,4-dihydro-tetrazol-5-one, l-(3,4-bis-trifluoromethyl-phenyl)-l,4-dih.ydro-tetrazol-5-one, l-(3-fluoro-5-trifluoromethyl-phenyl)-l,4-dihydro-tetrazol-5-one, l-(3,5-dicrjloro-phenyl)-l54-dihydro-tetrazol-5-one) (SjS-dimethoxy-pheny -l -dihydro-tetrazol-S-one, l-(3,5-bis-trifluoromethyl-phenyl)-l,4-dihydro-tetrazol-5-one5 l -(3 -chloro-2-methoxy-5 -methyl-phenyl)-1,4-dihydro-tetrazol-5-one, l-(2,2-difluoro-benzo[l,3]dioxol-5-yl)-l,4-dihydro-tetrazol-5-one, l -(2,2,3,3-tetrafluoro-2,3 -dihydro-benzo[ l ,4] dioxin-6-yl)-1,4-düiy dro-tetrazol-5-one, l-(2,2,3-trifluoro-233-dihydro-benzo[l,4]dioxin-6-yl)-l,4-dihydro-tetrazol-5-one, l -(2,3,3 -trifluoro-2,3 -dihydro-benzo[ l ,4] dioxin-6-yl)-1,4-dürydro-tetrazol-5 -one, l-(232,3,3}7-pentafluoro-2,3-dihydro-benzo[l,4]dioxin-6-yl)-l34-dihydro-tetrazol-5-one, l-(3,5-dichloro-2,6-diethyl-phenyl)-l,4-dihydro-tetrazol-5-one, l -thiophen-2-yl-1,4-dihydro-tetrazol-5 -one, l -benzyl-134-dürydro-tetrazol-5-one, l-(4-fluoro-benzyl)-1,4-dihydro-tetrazol-5-one, l-(4-chloro-benzyl)-l,4-dihydro-tetrazol-5-one, l -(4-trifluoromethyl-benzyl)-1,4-dihydro-tetrazol-5 -one, l -[ l -(2-fluoro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one, l - [ l -(2-chloro-phenyl)-ethyl] -1,4-dihydro-tetrazol-5-one, l -[ l -(2-trifluoromethyl-phenyl)-ethyl]-1,4-dihydro-tetrazol-5 -one, l -[ l -(3-fluoro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one, l -[ l -(3-chloro-phenyl)-ethyl]-1,4-dihy dro-tetrazol-5-one, l -[l -(3-trifluoromethyl-phenyl)-ethyI]-134-dihydro-tetrazol-5-one, l -[ l -(4-fluoro-phenyl)-ethyl] -1,4-dihydro-tetrazol-5-one, l -[ l -(4-chloro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one, l-[l-(4-trifluoromethyl-phenyl)-ethyl]-l,4-dihydro-tetrazol-5-one, l -[ l -(2,4-difluoro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one, l-[l-(234-dichloro-phenyl)-eth}fl]-l34-dihydro-tetrazol-5-one, l-[ l -(334-difluoro-phen}'l)-ethyl]-134-dihydro-tetrazol-5-one. Furthermore, there can be provided from the processes described in the literature, for example, l-(4-trifluoromethylphenyl)imidazolidin-2,4,5-trione from 4-trifluoromethylphenylurea (cf. J. Cliem. Soe. Perkin Trans. 2, 1977, 934, according to the process described in Chem. Ber. 1907, 40, 3737), there can be provided 3-(4-trifluorornethylphenyl)-lH-pyrazole from 4-trifluoromethylacetophenone, available on the market (cf. Synthesis 2001, 55-62), and further there can be provided 2-phenyl-2,4-dihydro-l,2,4-triazol-3-one and 2-(2-fluorophenyl)-234-dihydro-l32,4-triazol-3-one (cf. J. Prakt. Chem. 1907, 75, 131), and furthermore, there can be provided l-mono-(or di-)(trüluoromethyl)-phenyl-l34-dihydro-tetrazol-5-one by a reaction of mono-(or di-)(trifluoromethyl)phenyl isocyanate and known trimethylsüyl azide (cf. EP-A O 146 279, Chem. Plwrm. Bull, 1996,44, 314-327). The process to prepare the compounds of the above-mentioned formula (DQ can be conducted in an adequate diluent. As examples of the diluent used in that case there can be mentioned aliphatic, alicyclic and aromatic hydrocarbons (may be optionally chlorinated), for example, pentane, hexane, cyclohexane, petroleum ether, ligroine, benzene, toluene, xylene, dichloromethane; ethers, for example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF), dieüiylene glycol dimethyl ether (DGM); ketones, for example, acetone, methyl ethyl ketone (MEK), methyl isopropyl ketone, methyl isobutyl ketone (MEBK); niüiles, for example., acetonitrile, propionitrile, acrylonitrile; esters, for example, ethyl acetate, amyl acetate; acid amides, for example, dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone, l,3-dimethyl-2-imidazolidinone, hexamethyl phosphoric triamide (HMPA). The reaction can be conducted in the presence of an acid binder and as such an acid binder there can be mentioned, as inorganic base, hydrides, hydroxides, carbonates, bicarbonates, ete. of alkali metals and alkaline earth metals, for example, sodium hydride, lithium hydride, sodium hydrogen carbonate, potassiuni hydrogen carbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide; inorganic alkali metal amides, for example, lithium amide, sodium amide, potassium amide; as organic base, alcoholates, tertiary amines, dialkylaminoanilines and pyridines., for example, triethylamine, 1,1,4,4-tetramethylethylenediamine (TMEDA), N,N-dimethylaniline, N,N-diethylaniline, pyridine, 4-dimethylaminopyridine (DMAP), l34-diazabicyclo[2.2.2]octane (DABCO) and l,S-diazabicyclo[5.4.0]undec-7-ene (DBU). The reaction can also be conducted by a process using a phase-transfer catalyst. As examples of the diluent used in that case there can be mentioned water; aliphatic, alicyclic and aromatic hydrocarbons (may be optionally chlorinated), for example, pentane, hexane, cyclohexane, petroleum ether, ligroine, bensene, toluene, xylene; ethers, for example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF), diethylene glycol dimethyl ether (DGM). As examples of phase-transfer catalyst there can be mentioned, quaternary ions, for example, tetra-merhylammonium bromide, tetrapropylammonium brornide, tetrabutylammonium bromide, tetrabu-tylammonium bissulfate, tetrabutylammonium iodide, trioctylmethylammonium chloride, benzyl-triethylammoniuni bromide, butylpyridinium bromide, heptylpyridinium bromide, benzyltri-etiiylammonium chloride; crown ethers, for example, dibenzo-18-crown-6, dicyclohexyl-lS-crown-6, 18-crown-6; cryptands, for example, [2.2.2]-cryptate, [2.1.1]-cryptate, [2.2.1]-cryptate, [2.2.B]-cryptate, [202O2S]-cryptate, [3.2.2]-cryptate. The reaction can be conducted in a substantially wide range of temperature. It can be conducted at the temperatures in a range of generally about 0°C to about 200°C, preferably room temperature to about 150°C. Although said reaction is conducted desirably under normal pressure, it can be operated also under elevated pressure or under reduced pressure. In conducting Üie reaction, the aimed compounds can be obtained, for example, by reacting l mole amount to a little excess amount of a compound of the formula QÖI) to l mole of the compounds of the formula (XT) in a diluent, for example, DMF, in the presence ofpotassium carbonate. As specific examples of the compounds of the aforementioned formula (IX), obtained according to the above-mentioned process, there can be mentioned, for example, l-(4-nitro-benzyl)- IH-pyrrole, l-(3-memyl-4-nitro-benzyl)-lH-pyrazole, 3-methyl-l-(3-meth}'l-4-nitro-benzyl)-lH-pyrazole, 4-methyl-1 -(3-methyl-4-nitro-benzyl)- IH-pyrazole, 4,5 -dichloro-1 -(3 -methyl-4-nitro-benzyl)- IH-imidazole, l-(3-methyl-4-nitro-benzyl)-lH-l ,2,3-triazole, l-(3-methyl-4-nitro-benzyl)-lH-l,2,4-triazole, l -(3 -methyl-4-nitro-benzyl)-1 H-tetrazole, 5-methyl-1 -(3 -methyl-4-nitro-benzyl)- IH-tetrazole, 5-(2-chloro-phenyl)-l-(3-methyl-4-nitro-benzyl)-lH-tetrazole, 5-(3-trifluoromethyl-phenyl)-l-(3-methyl-4-nitro-benzyl)-lH-tetrazole, 5-(4-1rifluorometfryl-phenyl)-1 -(3-methyl-4-nitro-benzyl)- IH-tetrazole, 5-(3,5-bis-trifluoromethyl-phenyl)-l-(3-meÜa}d-4-nitro-benzyl)-lH-tetrazole; 5-(3-trifluoromethoxy-phenyl)-l-(3-rnethyl-4-nitro-benzyl)-lH-tetrazole, l-(3-methyl-4-mtro-berjzyl)-3-(4-trifluoromethyl-phenyl)-irnidazolidin-2-one5 l -(3 -methyl-4-iütro-benzyl)-3 -(4-trifluorometüyl-phenyl)-1,3-dihydro-imidazol-2-one, l -(3 -methyl-4-nitro-benzyl)-3 -(4-triflu.oromethyl-phenyl)-imidazolidin-2,4-dione, l-(3-mefhyl-4-nitro-benzyl)-3-(4-1rifluoromemyl-phenyl)-irrddazolidin-2,4,5-trione, l-(3-niethyl-4-nitro-benzyl)-3-(4-trifluoromethyl-phenyl)-lH-pyrazole, 2-(2-fluoro-phenyl)-4-(3-methyl-4-nitro-benz3'l)-2,4-dihydro-l,2,4-triazol-3-one, 2-(2-chloro-phenyl)-4-(3-methyl-4-nitro-benzyl)-2,4-dihydro-l,2,4-triazol-3-one, 4-(3-methyl-4-nitro-benzyl)-2-(2-tiifluoromethyl-phenyl)-2)4-dihydro-l,2;4-triazol-3-one) 2-(3 -fluoro-phenyl)-4-(3 -meth}'l-4-nitro-benzyl)-2,4-dihy dro-1,2,4-triazol-3 -one, 2-(3-chloro-phenyl)-4-(3-methyl-4-nitro-benzyl)-2,4-dihydro-l,2,4-triazol-3-one, 4-(3-methyl-4-nitro-benzyl)-2-(3-trifluorometl-iyl-phenyl)-2,4-düaydro-l,2,4-triazol-3-one, 2-(4-fluoro-phenyl)-4-(3-metliyl-4-nitro-benzyl)-2,4-dihydro-l,2,4-triazol-3-one, 2-(4-chloro-phenyl)-4-(3 -methyl-4-nitro-benzyl)-2,4-dihydro-1,2,4-triazol-3 -one, 4-(3-memyW-nitro-benzyl)-2-(4-trifluoromethyl-phenyl)-2,4-dihydro-l,2,4-triazol-3-one, 2-(3,4-bis-trifluoromethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-2,4-dihydro-l,2,4-triazol-3-one, 2-(3,5-bis-trifluoromethyl-phenyl)-4-(3 -methyl-4-nitro-benz3'l)-2,4-dihydro-1,2,4-triazol-3 -one, 4-(3-meftyl-4-nitro-benzyl)-5-1rifiuoromethy 3-one, 4-(2-cUoro-phenyl)-2-(3-methyl-4-ni1ro-benzyl)-234-dihydro-l,2,4-tiiazol-3-one3 2-(3-methyl-4-ni1io-benzyl)-4-(4-1iifluoromethyl-phenyl)-2,4-dihydro-l,2,4-triazol-3-oneJ 5-methyl-2-(3-methyl-4-iiitro-benzyl)-4-(4-ti 4-(2-cMoro-phenyl)-2-(3-methyl-4-mtrö-benzyl)-5-methylsulfäml-2)4-dihydro-l,234 2-(3-methyl-4-nitro-beoo2yl)-5-methylsulf 3-one, l-meftyl-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one, l-ethyl-4-(3-methyl-4-nitro-benzyl)-l)4-dihydro-tetrazol-5-one, l -propyl-4-(3 -methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5 -one, l -isobutyl-4-(3 -methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-S-one, l -(3-methyl-4-nitro-benzyl)-4-(2J2,2-trifluoro-ethyl)-1,4-dihydro~tetrazol-5-one, l-(3-methyl-4-nitro-benzyl)-4-(41434-trifluoro-butyl)-l34-dibydro-tetrazol-5-oneJ l-(3-methyl-4-ni1xo-benzyl)-4-(333,3-trichloro-2-mefhyl-propyl)-l,4-dihydro-tetrazol-5-one., l -cycldpropyl-4-(3-methyl-4-nitro-benzyl)-134-dihydro-tetrazol-5-one, l-cyclohexyl -fS-methyM-nitro-benzyl-l-dihydro-tetrazol-S-one., l-(3-methyl-4-nitro-benzyl)-4-phenyl-l34-dihydro-tetrazol-5-one, l-(2-fluoro-phenyl)-4-(3-methyl-4-nitro-benzyl)-l,4-dih.ydro-tetrazol-5-one3 l-(2-chloro-phenyl)-4-(4-nitro-benzyl)-l,4-dih.ydro-tetrazol-5-one3 l-(2-chloro-phenyl)-4-(3-methyl-4-mtro-benzyl)-l,4-dihydro-tetrazol-5-one3 l-(2-chloro-phenyl)-4-[l-(3-methyl-4-nitro-phenyl)-ethyl]-lJ4-dihydro-tetrazol-5-one, l -(3-methyl-4-nitro-benzyl)-4-(2-methyl-phenyl)-1,4-dihydro-tetrazol-5 -one, l-(3-methyl-4-nitro-benzyl)-4-(2-methoxy-phenyl)-l34-dihydro-tetrazol-5-one, l-(3-methyl-4-nitro-benzyl)-4-(2-trifluoromethyl-phenyl)-l,4-dihydro-tetrazol-5-one3 l-(3-methyl-4-nitro-benzyl)-4-(2-trifluoromethoxy-phenyl)-l,4-dihydro-tetrazol-5-one, l-(3-fluoro-phenyl)-4-(3-methyl-4-nitro-benzyl)-l,4-dihydro-tetrazol-5-one3 l-(3-chloro-phen.yl)-4-(3-methyl-4-riitro-benzyl)-l34-dih.ydro-tetrazol-5-one3 l-(3-methyl-4-nitro-benzyl)-4-(3-methyl-phenyl)-l34-dihydro-tetrazol-5-one3 l-(4-nitro-benzyl)-4-(3-trifluoromethyl-phenyl)-l34-dihydro-tetra2ol-5-one; l-(3-methyl-4-nitro-benzyl)-4-(3-trifluoromethyl-phenyl)-l ,4-dihydro-tetrazol-S-one, . l-(3-difluoromethoxy-phenyl)-4-(3-met;hyl-4-nitro-benzyl)-l,4-dihydro-tetrazol-5-one3 l-(3-methyl-4-nitro-benzyl)-4-(3-trifluoromethoxy-pb.enyl)-l34-diliydro-tetrazol-5-one3 l-(4-fluoro-phenyl)-4-(3-methyl-4-nitro-benzyl)-l34-dihydro-tetrazol-5-one, l-(4-chloro-phenyl)-4-(3-methyl-4-nitro-benzyl)-l34-dihydro-tetrazol-5-one3 l-(4-bromo-phenyl)-4-(3 -methyl-4-nitro-benzyl)-134-dib.ydro-tetrazol-5-one3 l-(3-methyl-4-nitro-benzyl)-4-(4-methyl-phenyl)-l34-düiydro-tetrazol-5-one, l-(4-isopropyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-l34-dLhydro-tetrazol-5-one3 l-(4-nitro-benzyl)-4-(4-trifluoromethyl-phenyl)-l.,4-dihydro-tetrazol-5-one3 l -(2-cMoro-4-nitro-benzyl)-4-(4-trifluoromethyl-phenyl)- 1 34-dihydro-tetrazol-5-one, l-(3-cliloro-4-m1ro-benzyl)-4-(4-trifluoromethyl-phenyl)-l,4-düiydro-tetrazol-5-one) l-(3-methyl-4-nitro-benzyl)-4-(4-trifliioroinefhyl-phenyl)-l,4-dihydro-tetrazol-5-oneJ l -(4-difluoromethoxy-phenyl)-4-(3-methyl-4-nitro-benzyl)- 1 ,4-düiydro-tetrazol-5-one, l-(3-mettiyl-4-nitro-berizyl)-4-(4-trifluoromethoxy-phenyl)-l)4-düiydro-tetrazol-5-oneJ !-(3-methyl-4-nitro-benzyl)-4-(4-trifluoromethylsulfanü-phenyl)-l,4-düiydro-tetrazol-5-oneJ !-(3-me1hyl-4-ni1io-benzyl)-4-(4'-trifluoromethyl-biphenyl-4-yl)-l)4-dihydro-tetrazol-5-one) l -(3 ' ,5 ' -bis-trifluoromethyl-biphenyl-4-yl)-4-(3 -meÜ-iyl-4-nitro-benzyl)- 1 ,4-dihydro-tetrazol-5-one, l -(4-bromo-2-fluoro-phenyl)-4-(3 -methyl-4-nitro-benzyl)- 1 ,4-dihydro-tetrazol-5-one, l -(2-fluoro-3 -trifluoromethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)- 1 54-dihydro-tetrazol-5-one, -% l -(3-bromo-4-trifluoromethoxy-phenyl)-4-(3-methyl-4-nitro-benzyl)- 1 ,4-dihydro-tetrazol-5-one, l -(3-chloro-4-trifluoromethoxy-phenyl)-4-(3-methyl-4-mtro-benzyl)- 1 34-dihydro-tetrazol-5-one., l-(4-fluoro-3-üifluoromethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-lJ4-dihydro-tetrazol-5-one, l-(2-fluoro-5-1rifluoromethyl-phenyl)-4-(3-methyl-4-iiitro-benzyl)-lJ4-dihydro-tetrazol-5-one, l -(4-chloro-3-trifluoromethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)- 1 34-düi)'dro-tetrazol-5-one,, l-(3,4-bis-trifluoromethyl-phenyI)-4-(3-methyl-4-iiitro-benzyl)-l,4-dihydro-tetrazol-5-one, l-(3-fluoro-5-trifluoromethyl-phenyl)-4-(3-methyl-4-mtro-benzyl)-l,4-dihydro-tetrazol-5-one; l-(3,5-dichloro-phenyl)-4-(3-methyl-4-nitro-benzyl)-l,4-dihydro-tetrazol-5-one., l-(3,5-dimethoxy-phenyl)-4-(3-methyl-4-nitro-benzyl)-l)4-dihydro-tetrazol-5-one, l-(3,5-bis-trifluoromethyl-phenyl)-4-(2-ch]oro-4-nitro-benzyl)-l,4-dihydro-tetrazol-5-one, l-(335-bis-trifluoromethyl-phenyl)-4-(3-ch]oro-4-nitro-benzyl)-l,4-dihydro-tetrazol-5-one; l-(3J5-bis-trifluoromethyl-phenyl) -(3-methyl-4-nitro-benzyl)-l,4-dihydro-tetrazol-5-one) l-(3,5-bis-trifluoromethyl-phenyl)-4-(2-methoxy-4-nitro-benzyl)-l,4-diliydro-tetrazol-5-one, l-(3,5-bis-1rifluoromethyl-phenyl)-4-(3-methoxy-4-nitro-benzyl)-l;4-dihydro-tetrazol-5-one, l-(3,5-bis-trifluoromethyl-phenyl)-4-(3.,5-dirnethyl-4-nitro-benzyl)-l,4-dihydro-tetrazol-5-one) l-(3J5-bis-trifluoromethyl-phenyl)-4-[l-(3-methyl-4-nitro-phenyl)-ethyl]-l,4-dihydro-tetrazol-5-one, l -(3-chloro-2-methoxy-5-meÜi3'l-phenyl)-4-(3 -methyl-4-nitro-benz)'l)- 1 -dihj o-tetrazol-S-one, l-(2,2-difluoro-benzo[l,3]dioxol-5-yl)-4-(3-methyl-4-nitro-benzyl)-l,4-dihydro-tetrazol-5-oneJ l-(3-methyl-4-nitro-benzyl)-4-(2,23J3-tetrafluoro-2;3-dihydro-benzo[l,4]dioxin-6-yl)-l34-dihydro- tetrazol-5-one, l -(3 -methyl-4-nitro-benzyl)-4-(2,2,3 -trifluoro-2,3 -dihydro-benzo[ l ,4] dioxin-6-yl)- 1 ,4-dihydro- tetrazol-5-one, l -(3 -methyl-4-nitro-benzyl)-4-(2,3 ,3 -trifluoro jS-dihydro-benzo [ l ,4] dioxin-6-yl)-l ,4-dihydro- tetrazol-5-one, l-(3-methyl-4-nitro-benzyl)-4-(232)333J7-pentafluoro-253-dihydro-benzo[l)4]dioxin-6-yl)-lJ4- düiydro-tetrazol-5-one, l-(3,5-dichloro-236-diethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-l,4-dihydro-tetrazol-5-one, l -benzyl-4-(3 -methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5 -one, l -(4-fluoro-benzyl)-4-(3 -methyl-4-nitro-benzyl)-134-dibydro-tetrazol-5-one, l -(4-chloro-benz)'l)-4-(3-methyl-4-nitro-benzyl)-1 34-dihydro-tetrazol-5-one, l -(3-methyl-4-nitro-benzyl)-4-(4-trifluoromethyl-benzyl)-1,4-dihydro-tetra2ol-5-one, l -[ l -(2-fluoro-phenyl)-ethyl]-4-(3-methyl-4-nitro-benzyl)-134-dihydro-tetrazol-5-one, l-[l-(2-cliloro-phenyl)-ethyl]-4-(3-methyl-4-nitro-benzyl)-l,4-dihydro-telTazol-5-oneJ l-(3-methyl-4-nitro-benzyl)-4-[l-(2-1rifluoromethyl-phenyl)-eÜiyl]-lJ4-dihydro-tetrazol-5-one, l-[l-(3-fluoro-phenyl)-ethyl]-4-(3-methyl-4-nitro-benzyl)-l)4-dihydro-tetrazol-5-one) l - [ l -(3-chloro-phenyl)-ethyl]-4-(3 -methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5 -one: l-(3-metliyl-4-nitro-benzyl)-4-[l-(3-trifluoromeÜayl-phenyl)-ethyl]-lJ4-dihydro-tetrazol-5-oneJ l-[l-(4-fluoro-pb.enyl)-ethyl]-4-(3-methyl-4-nitro-benzyl)-l,4-dihydro-tetrazol-5-one, l -[ l -(4-chloro-phenyl)-ethyl]-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one, l-(3-me(hyl-4-nitro-benz}d)-4-[l-(4-trifluoromethyl-phenyl)-ethyl]-l,4-dihydro-tetrazol-5-one, l - [ l -(2,4-difluoro-phenyl)-ethyl]-4-(3-methyl-4-nitro-benzyl)-1 -dihydro-tetrazol-S-one, l - [ l -(2,4-dichloro-phenyl)-ethyl]-4-(3 -methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one, l-[l-(3)4-difluoro-phenyl)-ethyl]-4-(3-meÜi}'l-4-nitro-benzyl)-l34-dihydro-tetrazol-5-one. And as specific examples of the compounds of the formula (TV), starting materials in the preparation process (b), there can be mentioned, for example, 2-{2-meth}d-4-[5-oxo-4-(2-cMoro-phenyl)-435-dmydro-tetrazol-l-ylmethyl]-phenyl}-isoindol-l,13- dione-, 4-fluoro-2- {2-methyM-[5-oxo-4-(2-chloro-phenyl)-435-diliydro-tetrazol-1 -ylmethyl]-phenyl} - isoindol-1,3-dione, 4-chloro-2-{2-methyl-4-[5-oxo-4-(2-chloro-phenyl)-435-dihydro-tetrazol-l-ylmethyl]-phenyl}- isoindol-1,3-dione, 4-bromo-2- {2-methyl-4-[5-oxo-4-(2-chloro-phenyl)-4,5-dihydro-tetrazol-1 -ylmethylj-phenyl}- isoindol-1,3-dione, 4-iodo-2- {2-methyl-4-[5 -oxo-4-(2-chloro-phen}'l)-4,5-dihydro-tetrazol-1 -ylmethyl] -phenyl} -isoindol- 1,3-dione, 4,7-dichloro-2-{2-methyl-4-[5-oxo-4-(2-chioro-phenyl)-435-dihydro-tetrazol-l-ylmet:hyl]-phenyl}- isoindol-1,3-dione, 5,6-dicUoro-2-{2-me1hyl-4-[5-oxo-4-(2-cliloro-phenyl)-4,5-dih}'dro-tetrazol-l-ylmethyl]-phenyl}- isoindol-l33-dione, 4-nitro-2-{2-methyl-4-[5-oxo-4-(2-chloro-phenyl)-4,5-dihydro-tetrazol-l-ylmethyl]-phenyl}- isoindol-1,3 -dione, 4-methyl-2-{2-methyl-4-[5-oxo-4-(2-chloro-phen34)-4,5-dihydro-tetrazol-l-ylmethyl]-phen)4}- isoindol-1,3-dione, 2- (2-methyl-4-[5 -oxo-4-(4-trifluoroinethyl-phenyl)-4,5-dihydro-tetrazol-1 -yknethyl] -phenyl} - isoindol-1,3-dione, 4-fluoro-2-{2-me&yl-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-435-dihydro-tetrazol-l-yImethyl]- phenyl}-isoindol-1,3-dione, 4-cUoro-2-{2-methyl-4-[5-oxo-4-(4-trifluoromeftyl-phenyl)-4,5-dihydro-tetrazol-l-ylmethyl]- phenyl} -isoindol-1,3-dione, 4-bromo-2-{2-methyI-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-l-ylniet;hyl]- phenyl}-isoindol-1,3-dione, 4-iodo-2-{2-me1±Lyl-4-[5-oxo-4-(4-trifluorome1hyl-phenyl)-4,5-dih)'dro-tetrazol-l-ylmethyl]-phenyl}- isoindol-1,3-dione, 4,7-dichloro-2- {2-methyl-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1 -ylmethyl]- phenyl}-isoindol-1,3-dione, 5,6-dicMoro-2-{2-methyl-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-l-ylmethyl]- phenyl}-isoindol-1,3-dione, 4-ni1ro-2-{2-methyl-4-[5-oxo-4-(4-trifluoromet;hyl-phen}'l)-4,5-dihydro-tetrazol-l-ylmethyl]- phenyl}-isoindol-1,3-dione, 4-me1iyl-2-{2-methyl-4-[5HDxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydTO-tetrazol-l-ylmel:hyl]- phenyl} -isoindol-1,3-dione, 2-{2-methyl-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-l-ylmethyl]-phenyl}- isoindol-l,3-dione., 4-fluoro-2-{2-meth}4-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phenyl)-4,5-dihydro-tetra2ol-l-ylmeth3'l]- phenyl} -isoindol-1,3-dione, 4-cMoro-2-{2-methyl-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phen)'l)-4,5-dihydro-tetrazol-l-ylmethyl]- phenyl}-isoindol-1,3-dione, 4-bromo-2-{2-methyl-4-[5-oxo-4-(3,5-bis-tri'fluorome1:hyl-phen}d)-4,5-diliydro-tetrazol-l-ylmethyl]- phenyl} -isoindol-1,3-dione, 4-iodo-2-{2-methyl-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-l-yknethyl]- phenyl}-isoindol-1,3-dione, 4,7-dichloro-2- {2-methyl-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phenyl)-4,5 -dihydro-tetrazol-1 - ylmethylj-phenyl} -isoindol-1,3-dione, 5,6-dichloro-2-{2-methyl-4-[5-oxo-4-(3,5-bis-trifl.uoromethyl-phenyl)-4,5-dihydro-tetrazol-l- ylmethylj-phenyl} -isoindol-1,3-dione, 4-nitro-2-{2-methyl-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-l-ylmethylj- phenyl} -isoindol-1,3 -dione, 4-metyl-2-{2-methyl-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phenyl)-4,5-dih)'dro-tetrazol-l-ylniethyl]- phenyl} -isoindol-1,3-dione. The compounds of the formula (V), starting materials in the preparation process (b), are either well-known compounds in the field of organic chemistry or can be synthesižed according to the process described in DE-A 20 45 905, WO 01/23350 ete. As their specific examples there can be mentioned ethylamine, diethylamine, n-propylamine, isopropylamine, n-butylamine, sec-butylamine, isobutyl-amine, t-butylamine, t-amylamine, cyclopropylamine, cyclopentylamine, cyclohexylamine, 3-methyl-cyclohexylamine, 2-(methylthio)-ethylamine, 2-(ethyltMo)-emylamine, l-methyl-2-(methylthio)-ethylamine, l,l-dimethyl-2-(methylthio)-ethylamine, ete. Compounds of the formula (VI), starting materials in the preparation process (c), include known compounds or can be easily' obtained according to the process described in EP-A 0919 542, EP-A l 006 107 ete. and as their specific examples there can be mentioned, N-isopropyl-phthalamic acid, 3 -fiuoro-N-isopropyl-phthalamic acid, 3 -chloro-N-isopropyl-phthalamic acid, 3 -bromo-N-isopropyl-phthalamic acid, 3-iodo-N-isopropyl-phthalamic acid, N-isopropyl-3-nitro-phthalamic acid, . N-(l -methyl-2-methylsulfanil-ethyl)-phthalamic acid, 3-fiuoro-N-(l -methyl-2-methylsulfanil-ethyl)-phthalamic acid, 3-chloro-N-(l-methyl-2-methylsulfanil-ethyl)-phthalamic acid, 3-bromo-N-( l -methyl-2-metliylsulfanil-ethyl)-phtiialamic acid, 3-iodo-N-( l -methyl-2-methylsulfanil-ethyl)-phthalamic acid, N-(l-memyl-2-memylsulfanil-eth.yl)-3-nitro-phthalamic acid, N-( l, l -dimethyl-2-methylsulfanil-ethyl)-phthalamic acid, N-(l,l-dimethyl-2-methylsulfanü-ethyl)-3-fluoro-phthalamic acid, 3-chloro-N-( l, l -dimethyl-2-methylsulfanil-ethyl)-phthalamic acid, 3-bromo-N-(l,l-dimethyl-2-methylsulfanil-ethyl)-phthalamic acid, N-( l, l -dimethyl-2-methylsulfanil-ethyl)-3 -iodo-phthalamic acid, N-( l, l -dimethyl-2-methylsulfanil-ethyl)-3 -nitro-phthalamic acid, N-isopropyl-3 -methanesulfonyloxy-phthalamic acid, N-( l -memyl-2-methylsulfanil-ethyl)-3-methanesulfonyloxy-phthalamic acid, N-( l, l -dimethyl-2-methylsulfanil-ethyl)-3 -methanesulfonyloxy-phthalamic acid. The compounds of the above-mentioned formula (VT) can be easily obtained generally by reacting phthalic anhydrides of the formula (Figure Removed) wherein X and n have the same definition as aforementioned, and amines of the formula (Figure Removed)wherein R1 and R2 have the same definition as aforementioned. The above-mentioned compounds of the formula (XIH) and the cpmpounds of the formula (XIV) are all well-known in the field of organic chemistry and specifically there can be mentioned the following as examples. As examples of the compounds of the formula (XEET) there can be mentioned, phthalic anhydride, 3-fluorophthalic anhydride, 3-chlorophthalic anhydride., 3-bromophmalic anhydride, 3-iodophthalic anliydride, 3-methylphthalic anhydride, 3-nitrophthalic anhydride., 3,6-di-fluorophthalic anhydride, 3,6-dichlorophthalic anhydride, 4,5-dichlorophthalic anhydride, 3,4,5,6-tetrafluorophthalic anhydride, 3,4,5,6-tetrachlprophthalic anhydride, 3-methanesulfonyloxyphtlialic anhydride. As examples of the compounds of the formula (XIV) there can be mentioned, ethylamine, n-propylamine, isopropylamine, n-butylamine, sec-butylamine, isobutylamine, t-butyl- amine, t-amylamine, cyclopropylamine, cyclopentylamine, cyclohexylamine, 2-(metli3'lthio)-ethyl- amine, 2-(ethylthio)-ethylamine, l-methyl-2-(methyltlTio)-ethylamine, l,l-dimethyl-2-(methylthio)- ethylamine. These amines can be easily obtained also by the process described in DE-A 20 45 905, WO 01/23350. The reaction for synthesizing the compounds of the formula (VT) can be conducted according to the process described Org. Chem. 1981,46,175 ete. Such a reaction can be conducted in an adequate diluent and as examples of the diluent used in that case there can be mentioned aliphatic, alicyclic and aromatic hydrocarbons (may be optionally chlori-nated), for example, pentane, hexane, cyclohexane, petroleum ether, ligroine, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, dichlorobenzene; ethers, for example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF), dietiiylene glycol dimethyl ether (DGM); ketones, for example, acetone, methyl ethyl ketone (MEK), methyl isopropyl ketone, methyl isobutyl ketone (MffiK), ete.; nitriles, for example, acetonitrile, propionitrile, acrylonitrile; esters, for example, ethyl acetate, amyl acetate. The preparation process (e) can be conducted in the presence of a base and as such a base there can be mentioned tertiary amines, dialkylaminoanilines and pyridines, for example., triethylamine, 1,1,4,4-tetramethyleÜiylenediamine (TMEDA), N,N-dime1hylaniline, N,N-diethylaniline, pyridine, 4-dimethylaminopyridine (DMAP), l,4-diazabicyclo[2.2.2]octane (DABCO) and 1,8-diazabi-cyclo[5.4.0]undec-7-ene (DBU), ete. The reaction can be conducted in a substantially wide range of temperature. It can be conducted at the temperatures in a range of generally about -70°C to about 100°C, preferably about 50°C to about - V 80°C. Although said reaction is conducted desirably under normal pressure, it can be operated also under elevated pressure or under reduced pressure. In conducting the reaction., the aimed compounds can be obtained, for example, by reacting l mole amount to 4 mole amount of the compounds of the formula (XIV) to l mole of the compounds of the formula (Xm) in a düuent, for example, acetonitrile. The compounds of the formula (VII), starting materials in the preparation process (d), are novel compounds and can be easily obtained, for example, by reacting a compound represented by the formula (VHI-a) (Figure Removed)wherein X, n, A1, r, Q, A2, s and E have the same definition as aforementioned., in the presence of a condensing agent (cf. e.g. J. Med. Chem. 1967,10, 982). The compounds of the above-mentioned formula (VHI-a) are also novel compounds and can be easily obtained by reacting phthalic anhydrides of the aforementioned formula (X) and the compounds of the aforementioned formula (DI), in which R3 is a hydrogen atom. The above-mentioned reaction of a compound of the formula (VIE-a) and a compound of the formula (KT), in which R3 is a hydrogen atom, can be conducted in an adequate diluent and as examples of the diluent used in that case there can be mentioned aliphatic, alicyclic and aromatic hydrocarbons (may be optionally chlorinated), for example, pentane, hexane, cyclohexane, petroleum ether, ligroine, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, dichlorobenzene; ethers, for example, ethyJ ether, methy] ethyl ether, isopropyi etnsr, buryl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (TH#), dierh,vl» The reaction can be conducted in the presence of ,a base and as such a base there can be mentioned tertiary amines, dialkykia-incaniH. c-s mid pyriüines, for example, trieüaylamine, 1,1,4,4-tetramethyl-ethylenediamine (TMEDA), N,N-dimethylaniline, N,N-diethylaniline, pyridine, 4-dimethylami-nopyridine (DMAP), l,4-diazabicyclo[2.2.2]octane (DABCO) and l,S-diazabicyclo[5.4.0]undec-7-ene(DBU). The reaction can be conducted in a substantially wide range of temperature. It can be conducted at the temperatees in a range of generally about -70°C to about 100°C, preferably about -50°C to about 80°C. Although said reaction is conducted desirably under nomial pressure, it can be operated also under elevated pressure or under reduced pressure. In conducting the reaction, the aimed compounds can be obtained, for example, by reacting l mole amount to 4 mole amount of the compounds of the formula (ffl), in which R3 is a hydrogen atom, to l mole of the compounds of the formula (X) in a diluent, for example, acetonitrile. As specific examples of the compounds of the above-mentioned formula (Vm-a), there can be mentioned, for example, N. {4-[4-(2-chloro-phenyl)-5-oxo-4,5-dihydro-tetrazol-1 -yknethyl]-2-methyl-phenyl} -6-iodo- phthalamic acid, 6-iodo-N-{2-memyl-4-[5-oxo-4-(2-1rifluoromemyl-phenyl)-4,5-dihydro4etrazol-l-yh3iethyl]- phenyl}-phfhalamic acid, N-{4-[4-(4-fluoro-phenyl)-5-oxo-4,5-düiydro-te1razol-l-ylmeth.yl]-2-methyl-phenyl}-6-iodo-phthalamic acid, N-{4-[4-(4-cHoro-phenyl)-5-oxo-435-dihydro-tetrazol-l-ykQeihyl]-2-methyl-phenyl}-6-iodo-.phthalamic acid, 6-iodo-N-{2-methyl-4-[5-oxo-4-(4-trifluorometliyl-phenyl)-4,5-düiydro-tetrazol-l-ylmethyl]-phenyl} -phthalamic acid, ete. examples of the compounds of the ahove-mentioned formula (VII), there can be aihy dro-tetrazol-5 -one, !-(4-chloro-phenyl)-4-[4-(4-iodo-3-oxo-3H-isobenzofuran-l-ylideneainino)-3-me1hyl-beiizyl]-l34- dihydro-tetrazol-5-one, \? l -[4-(4-iodo-3 -oxo-3H-isobenzofuran- 1 -ylideneamino)-3 -methyl-benzyl]-4-(4-trifluoromethyl- phenyl)-l,4-dihydro-tetrazol-5-one., ete. The compounds of the formula (V), also starting materials in the preparation process (d), have been described in the aforementioned preparation process (b). The compounds of the formula O'7!!!)» starting materials in the preparation process (e), are compounds and can be easily obtained, as described 'in the aforementioned preparation process (d), generally by reacting phthalic anhydrides of the aforementioned formula (X) with the compounds of the aforementioned formula (TÜ). The reaction is the same as already described in the aforementioned preparation process (d). As specific examples of the compounds of the formula (VUI) there can be mentioned, N-{4-[4-(2-chloro-phenyl)-5-oxo-4,5-dihydro-tetrazol-l-yknethyl]-2-methyl-phenyl}-N-methyl-6-iodo-phthalamic acid, 6-iodo-N-{2-methyl-4-[5-oxo-4-(2-trifluoromethyl-phenyl)-4,5-dmydro-tetrazol-l-y]methyl]-phenyl} -N-methyl-phthalamic acid, N-{4-[4-(4-fluoro-phenyl)-5-oxo-4,5-dmydro-tetrazol-l-ylmethyl]-2-methyl-phenyl}-N-methyl-6-iodo-phthalamic acid, N-{4-[4-(4H3Horo-phenyl)-5-oxo-4,5-dihydro-terrazol-l-ylrnethyl]-2-methyl-phenyl}-N-methyl-6-iodo-phthalamic acid, 6-iodo-N-{2-methyl-4-[5-oxo-4-(4-trifluoromemyl-phenyl)-455-dihyoro-te1razol-l-ylmethyl]-N-methyl-phenyl}-phthalamic acid. The compounds of the formula (V), also starting materials in the preparation process (e), are identical with those in the aforementioned preparation processes (b) and (d). As another preparation process for the compounds of the aforementioned formula (VIU), the common starting materials in the preparation process (d) and preparation process (e), in which X and Y represent other groups than bromo or iodo, compounds of the formula (Figure Removed)wherein n, R3, m, A1, r, Q, A2, s and E have the same definition as aforementioned, and X1 and Y1 each has a definition of the aforementioned X and Y but excluding bromo and iodo, is reacted with a metal reagent, for example, butyl lithium, and then reacted with carbon dioxide to obtain the compounds of the corresponding formula (VTD) (however, X and Y do not represent bromo or iodo). The compounds of the above-mentioned formula (XV) are novel compounds and can be easily obtained generally by reacting a benzoic acid halide represented by the formula (Figure Removed)wherein X1 and n have the same definition as aforementioned, and Hai represents a halogen atom, with the compounds of the aforementioned formula (DI) (Figure Removed)wherein R3, Y, m, A1, r, Q, A2, s and E have the same definition as aforementioned. The compounds of the above-mentioned formula (XVI) are well-known compounds in the field of organic chemistry and there can be mentioned specifically, benzoyl chloride, 3-fluorobenzoyl chloride, 3-chlorobenzoyl chloride, 3-methylbenzoyl chloride, 3-nitrobenzoyl chloride. The reaction to prepare the compounds of the above-mentioned formula (XV) can be conducted in an adequate diluent and as examples of tlie diluent used in that case there can be mentioned aliphatic, alicyclic and aromatic hydrocarbons (may be optionally chlorinated), for example, pentane, hexane, cyclohexane, petroleum ether, ligroine, benzene, toluene, xylene, -dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, dichlorobenzene; ethers, for example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF),- diethylene glycol dimethyl ether (DGM); esters, for example, ethyl acetate, amyl acetate. The reaction can be conducted in the presence of an acid binder and as such an acid binder there can be mentioned, as inorganic base, hydroxides, carbonates, bicarbonates, ete. of alkali metals and alkaline earth metals, for example, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate., potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide; as organic base, alcoholates, tertiary amines, dialkylaminoanilines and pyridines, .for example, triethylamine, 1,1,4,4-teträmethylethylenediamine (TMEDA), N,N-dimethylaniline, N5N-diethylaniline, pyridine, 4-dimethylaminopyridine (DMAP), l,4-diazabicyclo[2.2.2]octane CDABCO) and l,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The reaction can be conducted in a substantially wide range of temperature. It can be conducted at the temperatures in a range of generally about-20 to about 150°C, preferably about 0°C to about 100°C. Although said reaction is conducted desirably under normal pressure, it can be operated also under elevated pressure or under reduced pressure. In conducting the reaction, the aimed compounds can be obtained, for example, by reacting l mole amount to a little excess amount of the compounds of the formula (DI) to l mole of the compounds of the formula (XVI) in a diluent, for example, 1,2-dichloroethane, in the presence of triethylamine. The compounds of the formula (Ii), starting materials in the preparation process (f), are the compounds included in the aforementioned formula (I) of the present invention. By oxidizing C1-C6-allcylthio-C1-C6-alkyl, the definition of RIf in the formula (If), compounds of the formula (I) corresponding to C1-C6-alkylsulfüiyl-C1-C6-alkyl or Ci-Cä-alkylsulfonyl-C1-C6-alkyl canbe obtained. The compounds of the formula (If) can be prepared by the aforementioned preparation processes (a), (b),(c),(d)and/or(e). As specific examples of the compounds of the formula (If) there can be mentioned, for example, 3-iodo-N2-(l-methyl-2-methylsulfanyl 4,5-dihydro-triazol-l-ylmethyl]-phenyl}-phtiialamide, phenyl)-4,5-dihydro-triazol- 1 -ylmethylj-phenyl} -phthalamide, 3-iodo-N2-(l-methyl-2-methylsulfanyl-ethyl)-N1-{2-me%l-4-[5-oxo-4-(4-1rifluoromethyl-phenyl)-4,5-dmydro-triazol-l -ylmethyl]-phenyl} -phthalamide, N2-(l,l-dimethyl-2-methylsulfanyl-ethyl)-3-iodo-N1-{2-methyl-4-[5-oxo-4-(4-trifluoromethyl-phenyl) -4.,5-dihydro-triazol- 1 -ylmethyl] -phenyl} -phthalamide, N1-{4-[4-(3]5-bis-tiifluoromemyl-phenyl)-5-oxo-4,5-dihydro-triazol-l-ylmethyl]-2-methyl-phenyl}-3-iodo-N2-(l-methyl-2-methylsulfanyl-eÜayl)-phthalamide, NI-{4-[4-(3,5-bis-trifluoromemyl-phenyl)-5-oxo-4,5-dihydro-1xiazol-l-ylme1hyl]-2-methyl-phenyl}-N2-(l , l -dimethyl-2-methylsulfanyl-ethyl)- 3-iodo-phthalamide, ete. The reaction of the aforementioned preparation process (a) can be conducted by using adequate diluents, singly or mixed, and as examples of the diluents used in that case there can be mentioned water; aliphatic, alicyclic and aromatic hydrocarbons (may be optionally chlorinated), for example., pentane, hexane, cyclohexane, petroleum ether, ligroine, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, dichlorobenzene; ethers, for example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, ditnethoxyethane (DME), tetrahydrofuran (THF), diethylene glycol dimethyl ether (DGM); nitriles, for example, . acetonitrile, propionitrile, acrylonitrile; esters, for example, ethyl acetate, amyl acetate. The preparation process (a) can be conducted in the presence of an acid catalyst and as examples of such an acid catalyst there can be mentioned mineral acids, for example, hydrochloric acid, sulfuric acid, organic acids, for example, acetic acid, trifluoroacetic acid, propionic acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid. The preparation process (a) can be conducted in a substantially wide range of temperature. It can be conducted at the temperatees in a range of generally about -20°C to about 100°C, preferably about 0°CtoaboutlOO°C. Although said reaction is conducted desirably ünder normal pressure, it can be operated also under elevated pressure or under reduced pressure. In conducting the preparation process (a), the aimed compounds can be obtained, for example, by reacting l mole amount to a little excess amount of the compounds of the formula (IH) to l mole of the compounds of the formula (ü) in a diluent, for example, 1,2-dichloröethane, in the presence of 0.01-0.1 mole aniount of p-toluenesulfonic acid. The preparation process (b) can be conducted in the presence of a base such as tertiary amines, dialkylaminoanilines and pyridines, for example, Iriethylamine, 1,1,4,4-telramethylethylenediarnine (TMEDA), N,N-dimethylaniline, N,N-diethylaniline, pyridine, 4-drmethylaminopyridine (DMAP), l,4-diazabicyclo[2.2.2]octane (DABCO) and l,8-diazabicyclo[5.4.0]undec-7-ene (DBU), ete. ' The preparation process (b) can be conducted in a substantially wide range of temperature. It can be conducted at the temperatures in a range of generally about -20°C to about 150°C, preferably room temperature to about 100°C. Although said reaction is conducted desirably under normal pressure, it can be operated also under elevated pressure or under reduced pressure. In conducting the preparation process (b), the aimed compounds can be obtained, for example, by reactmg l mole amount to 25 mole amount of the compounds of the formula (V) to l mole of the compounds of the formula (IV). The aforementioned preparation processes (c), (d) and (e) can be conducted under the similar conditions as for the above-mentioned preparation process (a). The reaction of the aforementioned preparation process (f) can be conducted in an adequate diluent and as examples of the diluents used in that case there can be mentioned aliphatic, alicyclic and aro-matic hydrocarbons (ma}' be optionally chlorinated), for example, benzene, toluene, xylene, dichloro-methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, dichlorobenzene; alcohols, for example, methanol, ethanol, isopropanol, butanol, acids: formic acid, acetic acid. As oxidizing agent to be used there can be mentioned, for example, metachloroperbenzoic acid, peracetic acid, potassium metaperiodate, potassium hydrogen persulfate (oxone), hydrogen peroxide. The preparation process (i) can be conducted in a substantially wide range of temperature. It can be conducted at the temperatures in a range of generally about —50°C to about 150°C, preferably about — 10°CtoaboutlOO°C. Although said reaction is conducted desirably under normal pressure, it can be operated also under elevated pressure or under reduced pressure. In conducting the preparation process (f), the aimed compounds can be obtained, for example, by reactrng l mole amount to 5 mole amount of an oxidizing agent to l mole of the compounds of the formula (Ii) in a diluent, for example, dichloromethane. The reaction of the preparation process (f) can be conducted according to the process described in, for example, Jildcen Kagaku Kohza (Lectures of experimental chemistry), compiled by the Chemical Society of Japan, 4 ed., Vol. 24, page 350 (1992) published by Maruzen or ibid., page 365. The compounds of the formula (I) of the present invention show strong insecticidal action. They can, therefore, be used. as insecticidal agents. And the active compounds of the formula (I) of the present invention exhibit exact controlling effect against harrnful insects without phytotoxicity against cultured plants. The compounds of the present invention can be used for controlling a wide variety of pests, for example, harmful sucldng insects, biting insects and other plant-parasitic pests, stored grain pests, hygienic pests, ete. and applied for their exterrhination. As examples of such pests there can be mentioned the following pests: As insects, there can be mentioned coleoptera pests, for example, Callosobruchus Chinensis, Sitophilus zeamais, Tribolium castaneum, Epilachna vigintioctomaculata, Agriotes fuscicollis, Anomala rufocuprea, Leptinotarsa decemlineata, Diabrotica spp., Manochamus alternatus, Lissorhoptrus oryzophüus, Lyctus bruneus; Lepidoptera pests, for example, Lymantna dispar, Malacosoma neustria,- Pieris rapae, Spodoptera h'tura, Mamestra brassicae, Chilo suppressalis, Pyrausta nubilalis, Ephestia cautella, Adoxophyes orana, Carpocapsa pomonella, Agrotis fucosa, Galleria mellonella, Plutella maculipennis., Heliothis virescens, Phyllocnistis citrella; Hemiptera pestc, for e?;ample, Nephotettix cincticeps, Nilaparvata lugens, Pseudococcus comstocki, Unaspis yanonensis, Myzus percicae, Aphis pomi, Aphis gossypii, Rhopalosiphum pseudobrassicas, Stephanitis nashi, Nazara spp., Cimex lectularius, Trialeurodes vaporariorum, Psylla spp.; Orthoptera pests, for example, Blat&lla germanica, Periplaneta americana, Gryllotalpa qfriccaia, Locusta migi-atoria migrqtoriodes; Homoptera pests, for example, Reticulitermes speratiis, Coptotermesformosanus; Diptera pests, for example, Musca domestica, Aedes aegypti, Hylemia platura, Culex pipieiis, Anopheles slnensis, Culex fritaeniorhynchus. Moreover, as mites there can be mentioned, for example, Tetranychus telcains, Tetranychus urticae, Panonyclms citri, Aculops pelekassi, Tarsonemits spp. Furthermore, as nematodes there can be mentioned, for example, Meloidogyne incognita, Bursaphelenchus lignicolus Mamiya et Kiyohara, Aphelenchoides basseyi, Heterodera glycines, Pratylenchus spp. In addition, in the field of veterinary medicine, the novel compounds of the present invention can be effectively used against various harmful animal-parasitic pests (endoparasites and ectoparasites), for example, insects and helminthes. As examples of such anirnal-parasitic pests there can be mentioned the following pests: As insects there can be mentioned, for example, Gastrophilus spp., Stomoxys spp., Trichodectes spp., Rhodnius spp., Ctenocephalides canis. As mites there can be mentioned, for example, Ornithodoros spp., hodes spp., Boophilus spp. In the present invention substances häving insecticidal action against pests, which indude all of them, are in some cases called as insecticides. The active compounds of the present invention can be made into customary formulation forms, when they are used as insecticides. As formulation fonns there can be mentioned, for example, sohitions, emulsions, wettable powders, water dispersible granules, suspensions, powders, foaming agents, pastes, tablets, granules, aerosols, active compound-impregnated natural and synthetic substances, rnicrocapsules, seed coating agents, formulations used with buming equipment (as burning equipment, for example, fumigation and smoking cartridges, cans, coils, ete.), ULV [cold mist, warm mist], ete. These formulations can be prepared according to per se known methods, for example, by mixing the active compounds with extenders, namely liquid düuents; liquefied gas diluents; solid diluents or carriers, and optionally by using surface-active agents, namely emulsifiers and/or dispersants and/or foam-forming agents. In case that water is used as extender, for example, organic solvents can be used also as auxiliary solvents. As liquid diluents or carriers there can be mentioned, for example, aromatic hydrocarbons (for example, xylene, toluene, alkylnaphthalene ete.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (for example, clllorobenzenes, ethylene chlorides, methylene chloride, ete,), aliphatic hydrocarbons [for example, cyclohexane ete. or paraffins (for example, mineral oil fractions ete.)], alcohols (for example, butanol, glycols and their ethers, esters, ete.), ketones (for' example., acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, ete.), strongly polar solvents (for example, dimethylformamide, dimethyl sulfoxide, ete.), and water. Liquefied gas diluents or carriers are substances that are gases at nonnal temperature and pressure and there can be mentioned, for example, aerosol propellants such as butane, propane, nitrogen gas, carbon dioxide, halogenated hydrocarbons. As solid diluents there can be mentioned, for example, ground natural minerals (for example, kaolin, clay, taie, chalk, quartz, attapulgite, montmorillonite, diatomaceous earth, ete.), ground synthetic minerals (for example, highly dispersed süicic acid, alumina, silicates, ete.). As solid carriers for granules there can be mentioned, for example, crushed and fractionated rocks (for example, -calcite, marble, pumice, sepiolite, dolomite, ete.) synthetic granules of inorganic and organic meals, partides of organic materials (for example, saw dust, coconut shells, maize cobs, tobacco stalks, ete.) ete. As emulsifiers and/or foam-forming agents there can be mentioned, for example, noniomc and anionic emulsifiers [for example, polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (for example, alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates, ete.)], albumin hydrolysis products, ete. Dispersants include, for example, lignin sulfite waste liquor and methyl cellulose. Tacldfiers can also be used in formulations (powders, granules, eraulsifiable concentrates). As said taclafiers there can be mentioned, for example, carboxymethyl cellulose, natural and synthetic polymers (for example, gum Arabic, polyvinyl alcohol, polyvinyl acetate, ete.). Colorants can also be used. As said colorants there can be mentioned, for example, inorganic pigments (for example, iron oxide, titanium oxide, Prussian Blue, ete,), organic dyestuffs such as alizarin d)'estuffs, azo dyestuffs or rnetal phthalocyanine dyestuffs, and further traces nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. Said formulations can contain the aforementioned active components of the amount in the range of generally 0.1-95 % by weight, preferably 0.5-90 % by weight. The active compounds of Üae formula (I) of the present invention can exist also as a mixed agent with other active compounds, for example, insecticides, poisonous baits, bactericides, miticides, nematicides, fungicides, growth regulators or herbicides in the form of their commercially usefül formulations or in tlie application forms prepared from such formulations. Here, as the above-mentioned insecticides, there can be mentioned, for example, organophosphorous agents, carbamate agents, carboxylate type chemicals, chlorinated hydrocarbon type chemicals, insecticidal substances produced by microbes, ete. Further, the active compounds of the formula (I) of the present invention can exist also as a mixed agent with a synergist and such formulations and application forms can be mentioned as commercially useful. Said synergist itself must not be active, but is a compound that enhances the action of the active compound. The content of the active compounds of the formula (T) of the present invention in a commercially useful application form can be varied in a wide range. The concentration of the active compounds of the formula (I) of the present invention at the time of application can be, for example, in the range of 0.0000001-100 % by weight, preferably in the range of 0.00001-1 %by weight. The compounds of the formula (I) of the present invention can be used by usual methods suitable to the application forms. In case of application against hygienic pests and stored grain pests the active compounds of the present invention have a good stability against alkali on a calcific substance and further show an excellent residual effectiveness in wood and soil. Then the present invention will be described more specifically by examples. The present invention, however, should not be restricted only to them in any way. Examples Synthesis Example l (Figure Removed)3-(l,l-Dimethyl-2-meAylthioetiiyliinino)-4-iodo-3H-isoBenzofuran-l-öne (0.94g) and l-(4-amino-3-memylbenzyl)-4-(4-trifluoromethylphenyl)-l,4-dihydrotetrazol-5-one (0.87 g) were dissolved in dichloromethane (10 ml), to which p-toluenesulfonic acid monohydrate (0.01 g) was added, and the mixture was stirred at room temperature for 3 hours. After finishing the reaction, water was added to the mixture and the organic layer was separated'and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography to obtain N2-(l,l-dimethyl-2-methyltiiioethyl)-3-iodo-NI-[2-methyl-4-(5-oxo-4-(4-trifluoromethylphenyl)-435-dihydrotetrazol-l-ykaethyl)phenyl]phthalarnide (0.6 g, mp. 83-87°C). Synthesis Example 2 (Figure Removed)NI-{4-[4-(3,5-bis-trifluoromethylphenyl)-5-oxo-4,5-dihydrotetrazol-l-ylrneÜiyl]-2-methyl-phenyl}-N2-(l,l-dimeäiyl-2-methyltlTioethyl)-3-iodo-phthalamide (0.5 g) was dissolved in dichloromethane, to which m-chloroperbenzoic acid (0.18 g) was added, and the mixture was stirred at room temperature for 5 hours. After finishing the reaction the mixture was washed successively with aqueous solution of sodium thiosulfate, saturated aqueous sohition of sodium hydrogen earbonate and saturated aqueous solution of sodium chloride and dried with anhydrous magnesium sulfate. After the solvent was distilled off, the obtained residue was purified by silica gel column chromatography to obtain N1-{4-[4-(3)5-bis-trifluoromemylphenyl)-5-oxo-435-dihydrotetrazol-l-ylmethyl]-2-methyl-phenyl}-3-iodo-N2-(2-methanesdfmyl-l3l-dimethylethyl)phthalamide (0.1 g, mp. 165-171°C). Synthesis Example 3 (Figure Removed)N2-(14-Dimethyl-2-methylthioethyl)-3-iodo- dihydrotetrazol-l-ylmethyl)phenyl]phthalamide (0.4 g) was dissolved in dichloromethane, to which m-chloroperbenzoic acid (0.24 g) was added, and the mixture was stirred at room temperature for 5 hours. After finishing the reaction the mixture was washed successively with aqueous solution of sodium thiosulfate, saturated aqueous solution of sodium hydrogen cafbonate and saturated aqueous solution of sodium chloride and dried with anhydrous magnesium sulfate. After the solvent was distilled off, the obtained residue was purified by silica gel column chromatography to obtain 3-iodo-N2-(2-methanesulfonyl-1, l -dimethylethyH-N1- {2-methyl-4-[5-oxo-4-(4-trifluoromethylphenyl)-4)5-dihydrotetrazol-l-yknethyl]phenyl}phthalamide (O.ldfg, mp. 108-112°C). Synthesis Example 4 (Figure Removed)2-{2-Methyl-4-[5-oxo-4-(4-1rifluoromethylphenyl)-4,5-dihydrote1razol-l-ylmethyl]phenyl}isomdol-1,3-dione (0.25 g) was dissolved in sec-butylamine (5 ml) and the mixture was stirred at room temperature for 5 hours. After finishing the reaction, the solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography to obtain the öbjected N-sec-but5d-N-{2-methyl-4-[5-oxo-4-(4-trifluoromethylphenyl)-4,5-dihydrotetrazol-l- yl-methyl]phenyl}phthalamide (0.2 g, mp. 217-218°C). Examples of the compounds of the formula (T) of the present invention obtained in the simüar manner to the Synthesis Examples l to 4 and the compounds of the formula (!) obtained easily by the preparation processes (a) to (f) are shown in the Table l to Table 4, together with the compounds obtained in the above-mentioned Synthesis Examples l to 4. In all tables the abbreviations mean Ph = phenyl, Me = methyl, Et = ethyl, n-Pr = n-propyl, i-Pr = iso-propyl. Tablel(r = Q. s =) (Figure Removed) (Table Removed)Q represents the following structures: (Figure Removed) (wherein the bond märked with * connects with A1 and the bond märked with # connects with A2) Table2(i=l,s=0) Q represents the following structures: (Table Removed) Q represents the following structures: (Figure Removed) (wherein the bond märked with * connects with A1 and the bond märked with # connects with A2) (Table Removed)Table 4(i=l. s=l) Q represents the following structures: O (Table Removed) Synthesis Example 5 (Starting Materjal Synthesis) (Figure Removed)To an ethanol solution (100 mL) of l-(3-mefeyl-4-nitrobenzyl)-4-(4-trifluoromethylphenyl)-l,4-dihydrotetrazol-5-one (9.4Sg) 10% palladium carbon (0.25g) was ädded and the mixture was stirred under hydrogen atmosphere at room temperature for 6 hours. After finishing tiie reaction, palladium carbon was filtered off and the solvent was distilled off under reduced pressure to obtain l-(4-amino-3-methyl-benzyl)-4-(4-trifluoromethyl-phenyl)-l,4-dihydrotetrazol-5-one (8.1 1 g, mp. 210-21 1 °C). Synthesis Example 6 (Starting Material Synthesis) (Figure Removed)In a similar manner as Synthesis Example 5, by using l-(3-niethyl-4-mtro-benzyl)-4-(3~trifluoro-methylphenyl)- 1 ,4-dihydrotetrazbl-5-one, l -(4-arnino-3-methyl-benz3'l)-4-(3-trifluoromethyl-phe-nyl)-l,4-dihydrotetrazol-5-one was obtained (mp. 89-94°C). Synthesis Example 7 (Starting Material Syntfaesis) (Figure Removed)In a similar manner as Synthesis Example 5, by using l-(3,5-bis-trifIuoromethyl-phenyl)-4-(3-me-thyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one, l -(4-amino-3 -methyl-benzyl)-4-(3,5-bis-trifiuoro-methyl-phenyl)-l,4-dihydro-tetrazol-5-one was obtained (mp. 129-130°C). Synthesis Example 8 (Starting Material Synthesis) (Figure Removed)3-Methyl-4-nitrobenzyl chloride (1.6 g), l-(4-trifluoromethylphenyl)-l,4-dihydrotetrazol-5-one (2.0 g) and potassium carbonate (1.4 g) w.ere stirred in DMF (50 ml) at room temperature for 5 hours. After finishing the reaction, water (100 ml) was added and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride (100 ml) and dried with magnesium sulfate. After the solvent was distilled off, the obtained residue was purified by silica .gel column chromatography to obtairi l-(3-methyl-4-iütrobenzyl)-4-(4-tri-fluoromethylphenyl)-l,4-dihydrotetrazol-5-one [2.6 g, 'H-NMR (CDC13, ppm) ; 2.6 (3H, s), 5.3 (2H, s), 7.4-8.3 (7H, m)]. Synthesis Example 9 (Starüng Materjal Synthesis) (Figure Removed)In a similar manner as Synthesis Example 8, by usingi-(3-trifluoromethyl-phenyl)-l,4-düiydro-te1ra-zol-5-one, l-(3-methyl-4-nitro-benzyl)-4-(3-trifluoromethyl-phenyl)-l34-dihydrotetrazol-5-one was obtained ['H-NMR (CDC13, ppm) ; 2.6 (3H, s), 5.2 (2H, s), 7.3-8.2 (7H, m)]. Synthesis Example 10 (Starting Materjal Synthesis) (Figure Removed)In a similar manner as Synthesis Example 8, by using l-(3,5-bis-trifluoromemyl-phenyl)-l,4-dilrydro-tetrazol-5-one in place of l-(4-trifluoromethyl-phenyl)-l,4-dihydro-tetrazol-5-one, l-(3,5-bis-trifluoromethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-l,4-dihydro-teti-azol-5-one was obtained [:H-NMR (CDC13, ppm); 2.6 (3H, s), 5.2 (2H, s), 7.2-8.0 (4H, m), 8.5 (2H, bs)j. Synthesis Example 11 (Starting Materjal Synthesis) (Figure Removed)3,5-Bis(trifluoromethyl) phenyl isocyanate (10.20 g) and trimethylsilyl azide (9.36 g) were stirred at 120-130°C for 10 hours. After the reaction mixture was brought to the room temperature, excess of trimethylsilyl azide was distilled off under reduced pressure and the obtained erude crystals were washed with petroleum ether to obtain l-(3,5-bis-trifluoromethyl-phenyl)-l,4-dihydro-tetrazol-5-one (11.05g,mp. 145-147°C). Synthesis Example 12 (Starting Materjal Synthesis) (Figure Removed)Phthalic anhydride (1.0 g) and l-(4-amino-3-methylbenz}4)-4-(4-trifluoromethylphenyl)-l,4-dihydro-tetrazol-5-one (2.4 g) were refluxed in 60ml of acetic acid for 3 hours. After finishing the reaction the solvent was distilled off under reduced pressure to obtain the objected 2-{2-methyl-4-[5-oxo-4-(4-trifluoromethylphenyl)-4,5-dihydrotetrazol-l-yhnethyl]phenyl}isoindol-l,3-dione [3.0g, ]H NMR (DMSO-do, ppm); 2.1 (3H, s), 5.2 (2H, s), 7.3-8.2 (HH,"m)]. Synthesis Example 13 (Starting Materjal Synthesis) (Figure Removed) l-(3-Methyl-4-nitrobenzyl)-3-(4-trifluoromethylphenyl)urea (1.0 g) was dissolved in 20 ml of dichloromethane, to which 5 ml of dichloromethane solution of oxalyl chloride (0.49 g) was added at room temperature, and the mixture was stirred for 8 hours. After the solvent was distilled off under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain the objected !-(3-me1hyl-4-ni1robenzyl)-3-(4-irifluoromemylphenyl)imidazolidin-2,4)5-trione [l.lg, 'H NMR (CDC13, ppm); 2.6 (3H, s), 4.9 (2H, s), 7.3-8.0 (7H, m)]. Synthesis Example 14 (Starting Material Synthesis) Methyl solutiou (5 ml) of 3-methyl-4-nitrobenzaldehyde (0.9 g) was added to a methanol suspen-sion (5 ml) of glycrne ethyl ester acetate (1.1 g) and sodium cyanotrihydroborate (0.53 g) at 0°C. After stirring the mixture at room temperatuure for 10 hours, 2N hydrochloric acid (10 ml) and ethyl acetate (10 ml) were added thereto. After removing the organic layer, IN aqueous solution of sodium hydroxide .(30 ml) was,added to the aqueous layer and extracted with ethyl acetate. After washing the organic layer with a saturated aqueous solution of sodium chloride (20 ml), it was dried with anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain the objected ethyl (3-metbyl-4-nitrobenzylamino)acetate [0.9 g, 'H NMR (CDC13, ppm) ; 1.2 (3H, t), 2.6 (3H, s), 3.4 (2H, s), 3.9 (2H3 s), 4.2 (2H, q), 4.8 (2H, s), 7.2-8.1 (3H, m)]. Synthesis Example 15 (Starting Material Synthesis) (Figure Removed)4-(trifluoromethyl)phenylisocyanate (0.83 g) was addedto a diethyl ether solution (50 ml) of ethyl (3-methyl-4-nitrobenzylamino)acetate (0.9 g) and the mixture was stirred vigorously at room tempe-rature for 7 hours. By filtering the crystals a erude product ethyl [l-(3-methyl-4-nitrobenzyl)-3-(4-trifluoromethylphenyl)ureido]acetate (0.8 g) was obtained and used in the next reaction without purification. Synthesis Example 16 (Starting Material Synthesis) (Figure Removed)Acetic acid solution (lO ml) of ethyl [l-(3-methyl-4-nitrobenzyl)-3-(4-trifluoromethylphenyl)-ureidojacetate (0.5 g) and concentrated hydrochloric acid (3 ml) was refluxed for 5 hours. After adding water (50 ml) the mixture was extracted with ethyl acetate. After washing the organic layer with water and a saturated aqueous solution of sodium chloride, it was dried with anhydrous magnesium sulfate. After the solvent was distüled off under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain the objected l-(3-methyl-4-nitrobenzyl)-3-(4-trifluoromethylphenyl)imidazolidin-2,4-dione [0.3 g, 'H NMR (CDC13, ppm) ; 2.7 (3H, s), 4.0 (2H, s), 4.8 (2H, s), 7.2-8.2 (7H, m)]. Synthesis Example 17 (Starting Material Synthesis) (Figure Removed)4-Chloromethyl-2-methyl-l-mtrobenzene (1.9 g), aminoacetaldehyde dimethyl acetal (6.3 g) and potassium carbonate (6.2 g) were mixed in acetonitrile (200 ml) and the mixture was refluxed for 20 hours. After adding water the mixture was extracted with ethyl acetate. After washing the organic layer with a saturated aqueous solution of sodium clüoiide, it was dried with anhydrous magnesium sulfate. After the solvent was distüled off under reduced pressure., the obtained residue was purified by silica gel column chromatography to obtain the objected (2J2-dimethoxyeÜiyl)-3-(methyl-4- ni1robenzyl)amine [2.5g, 'H NMR (CDC13, ppm) ; 2.6 (3H, s), 2.8 (2H, d), 3.5 (6H, s), 3.9 (2H, s), 4.6 (IH, m), 7.2-8.l (4H, m)]. Synthesis Example 18 (Starting Materjal Synthesis) (Figure Removed) (232-Dimemoxye%l)-3-(methyl-4-nitrobenzyl)arnine (1.2 g) was dissolved in ether (50 ml), to which 4-(trifluoromethyl)phenyl- isocyanate (l .3 g) was added at room temperature, and the mixture was stirred vigorously for l hours. After finishing the reaction, water was added to tiie mixture and it was extracted with ethyl acetate. After drying the organic layer with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain a erude product l-(2,2-dimethoxyethyl)-l-(3-methyl-4-nitrobenzyl)-3-(4-(trifluoromethyIphenyL)urea (1.8 g), which was used in the next reaction without purification. Synthesis Example 19 (Starting Materjal Synthesis) (Figure Removed)l-(2,2-Dimethoxyettiyl)-l-(3-me1iiyl-4-nitrobenzyl)-3-(4-(trifluorornethylphenyl)urea (1.8 g) was dissolved in THF (5 ml), to which 50 % aqueous solution of trifluoroacetic acid (20 ml), and the mixture was stirred at room temperature. After finishing the reaction and adding water, the mixture was extracted with ethyl acetate. After washing the organic layer with water and a saturated aqueous solution of sodium chloride, it was dried with anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain the objected l-(3-methyl-4-nitrobenzyl)-3-(4-(trifluoromethylphenyl)-l,3-dihydroimidazol-2-one [1.2 g, 'H NMR (CDC13, ppm) ; 2.6 (3H, s), 4.9 (2H, s), 6.4 (IH, d), 6.7 (IH, d), 7.2-8.1 (7H, m)]. Biological Test Example 1: Test against larva of Spodoptera litura Preparation of test agent: Solvent: Dimethylformamide 3 parts by weight Emulsifier. Polyoxyethylene alkyl phenyl ether 1 part by weight hi order to make an appropriate formulation of an active compound, 1 part by weight of the active compound was mixed with the above-mentioned amount of solvent containing the above-mentioned amount of emulsifier and the mixture was diluted with water to a prescribed concentration. Test method: Leaves of sweet potato were soaked in the test "agent diluted to a prescribed concentration with water, dried in the air and put in a dish of 9 cm diameter. 10 larvae of Spodoptera litwa at the third instar were placed on the leaves and kept in a room at the constant temperature of 25°C. After 2 and 4 days further leaves of sweet potato were added and after 7 days the number of dead larvae was counted and the rate of death was calculated. In this test the results of 2 dishes at 1 section were averaged. Test results: As specific examples the compounds of the compound no. 2-7, 2-35,2-67, 2-71, 2-72, 2-96, 2-140, 2-141, 2-142, 2-147, 2-173, 2-176, 2-181, 2-182, 2-270, 2-2S3, 2-293, 2-323, 2-333 and 2-337 showed 100% of rate of death at 20 ppm concentration of effective component. Biological Test Example 2: Test against larva of Cnaphalocrocis medinalis Guenee ■ Test method: Rice seedlings (cultivar: Tamanishiki) of 4-5 leaf stage, planted in a vinyl pot (9 cm diameter) were sprayed with the diluted aqueous solution of the prescribed concentration of the active compound prepared in the same manner as in the above mentioned Biological Test Example 1. After drying, top 1/3 part of the leaves of the plants was cut and put into a Petri-dish (9 cm diameter), in which a piece of filter paper (9 cm diameter) was laid and moistened. Five larvae of Cnaphalocrocis medinalis at the second instar were released in the Petri-dish and the dish was placed in a room at the constant temperature of 25°C. After 2 and 4 days, another 1/3 part of the plant leaves was cut and added to the dish. After seven days, the number of dead larvae was counted and the rate of death was calculated. In this test the results of 2 dishes at 1 treatment were averaged. Test results: As specific examples the compounds of the compound no. 2-12, 2-17, 2-50, 2-54, 2-140, 2-141, 2-154, 2-172, 2-173,2-234,2-248,2-253, 2-256,2-310, 2-333, 2-337, 4-8,4-15 and 4-16 showed 100% of rate of death at 20 ppm concentration of effective component Formulation Example l (Granule) To a mixture of 10 parts of the compound of the present invention (No. 2-7), 30 parts of bentonite (montmorillonite), 58 parts of taie and 2 parts of ligninsulfonate salt, 25 parts of water are added, well kneaded, made into granules of 10-40 mesh by an extrusion granulator and dried at 40-50°C to obtain granules. Fomiulation Example 2 (Granules) 95 Parts of clay mineral partides häving partide diameter distribution in the range of 0.2-2 mm are put in a rotary mixer. While rotating it, 5 parts of the compound of the present invention (No. 2-173) are sprayed together with a liquid diluent, wetted uniformly and dried at 40-50°C to obtain granules. Formulation Example 3 (Emulsifiable Concentrate) 30 Parts of the compound of the present invention (No. 2-140), 55 parts of xylene, 8 parts of polyoxy-ethylene alkyl phenyl ether and 7 parts of calcium alkylbenzenesulfonate are mixed and stirred to obtain an emulsifiable concentrate. Formulation Example4 (Wettable Powder) 15 Parts of the compound of the present rnvention (No. 2-333), 80 parts of a mixture of white carbon (hydrous amorphous silicon oxide fine powders) and powder clay (1:5), 2 parts of sodium alkylbenzenesulfonate and 3 parts of sodium alkyhiaphthalenesulfonate-formalin-condensate are crushed and mixed to make a wettable powder. Formulation Example 5 (Water Dispersible Granule) 20 Parts of the compound of the present invention (No. 2-337), 30 parts of sodium ligninsulfonate, 15 parts of bentonite and 35 parts of calcined diatornaceous earth powder are well mixed, added with water, extruded with 0.3mm screen and dried to obtain water dispersible granules. WE CLAIM: 1. Phthalamide derivatives represented by the formula (Formula Removed) wherein X represents hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, nitro, cyano, C1-C6-alkyl-sulfonyloxy, C1-C6-haloalkylsulfonyloxy, phenylsulfonyloxy, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkylsulfinyl-C1- C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6- alkylsulfonylamino, bis(C1-C6-alkylsulfonyl)amino or C1-C6-alkoxycarbonyl, n represents 1, 2, 3 or 4, Y represents hydrogen, halogen, C1-C6alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, or cyano, m represents 1, 2, 3 or 4, R1 represents C1-C6-alkyl or C1-C6-alkyl which is mono- or poly- substituted by substituents selected from the group consisting of cyano, nitro, C1-C6-alkylaminosulfonyl, N,N-di(C1-C6- alkyl)aminosulfonyl, C1-C6-alkylsulfonylamino, N-C1-C6-alkylsulfonyl- N-C1-C6-alkylamino, C1-C6-alkyl-carbonylamino, halo-C1-C6-alkyl, N- C1-C6-alkyl-carbonyl-N-C1-C6-alkylamino, C1-C6-alkyl- thiocarbonylamino, N-C1-C6-alkylthiocarbonyl-N-C1- C6-alkylamino, C1-C6-alkoxyimino-C1-C6-alkyl, C1-C6-alkyl-aminocarbonyl, N,N-di(C1-C6-alkyl)-aminocarbonyl, C1-C6-alkyl-aminothiocarbonyl, N,N-di(C1-C6-alkyl)-aminothiocarbonyl, C1-C6-alkoxy-carbonylamino, C1-C6- alkoxy-carbonyl-C1-C6-alkylamino, C1-C6-alkylamino-carbonyloxy, N,N-di(C1-C6-alkyl)amino-carbonyloxy, C1-C6-alkoxy- thiocarbonylamino, C1-C6-alkoxy-thiocarbonyl-C1-C6-alkylamino, C1- C6-alkylamino-thiocarbonyloxy, N,N-di(C1-C6-alkyl)-amino- thiocarbonyloxy, C1-C6-alkylthio-carbonylamino, C1-C6-alkylthio- carbonyl-C1-C6-alkylamino, C1-C6- alkylamino-carbonylthio, N,N- di(C1-C6-alkyl)amino-carbonylthio, C1-C6-alkylthio-thiocarbonylamino, C1-C6-alkylthio-thiocarbonyl-C1-C6-alkylamino, C1-C6-alkylamino- thiocarbonylthio, N,N-di(C1-C6-alkyl)amino-thiocarbonylthio, C3-C6-cycloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylthio-C1-C6-alkyl, Ci-C6-alkylsulfinyl-C1-C6-alkyl and C1-C6-alkylsulfonyl-C1-C6-alkyl, or C3-C8-cycloalkyl which may be substituted by substituents selected from the group consisting of C1-C4-alkyl, C1-C4-alkylthio or C1-C2-alkylthio-Ci-C2-alkyl, R2 represents hydrogen or C1-C6-alkyl, R3 represents hydrogen or C1-C6-alkyl, A1 represents straight chain or branched chain C1-C6-alkylene, r represents 1, A2 represents straight chain or branched chain C1-C6-alkylen, C1-C6-haloalkylene C2-C8-alkenylene, C2-C8-haloalkenylene, C2-C8-alkynylene or C2-C8-haloalkynylene, s represents 0, Q represents a heterocyclic group selected from (Formula Removed) W1 represents halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloallkyl, C1-C6-haloalkoxy, C1-C6-haloalkylthio, C1-C6-haloalkylsulfinyl, C1-C6-haloalkylsulfonyl, C3-C6-cycloalkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1 -C-6-alkylsulfonyl-C1 -C6-alkyl, W3 represents hydrogen or has the same definition as the aforementioned W1, E represents phenyl, biphenyl, naphthyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, thienyl, furyl or pyrrolyl, wherein said group may be optionally substituted with one or more substituents selected from the below-mentioned group of substituents W2 wherein said substituents may be identical or different, W2 represents halogen, nitro, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkyl, C1-C6-haloalkoxy, C1-C6-haloalkylthio, C1-C6-haloalkylsulfinyl, C1-C6-haloalkylsulfonyl, C3-C6-cycloalkyl, C1-C6-alkylthio-C1 -C6-alkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl or C1-C6-alkylsulfonyl-C1-C6-alkyl, or represents C3-C5-alkylene, C3-C5-haloalkyylene, oxy-C2-C4-alkylene, oxy-C2-C4-haloalkylene, C2-C4-alkyleneoxy, C2-C4-haloalkylenoxy, C1-C3-alkylenedioxy or C1-C3-haloalkylenedioxy, in case that W2 are two adjacent substituents, and P represents 0, 1, or 2. 2. Process for the preparation of the compounds of the formula (I) as claim in claim 1, comprising (a) in case that R2 represents hydrogen, the step of reacting compounds of the formula (II) (Formula Removed) wherein R1, X and n have the same definition as mentioned in claim 1, with compounds of the formula (III) (Formula Removed) wherein R3, Y, m, A1, r, Q, A2, s and E have the same definition as mentioned in claim 1, in the presence of inert solvents. 3. Insecticidal compositions comprising at least one compound of the formula (I) as claimed in claim 1 in an amount of 0.1-95% by weight along with extenders.

Full Text

The present invention relates to novel phthalamide derivatives, to processes for their preparation and
to their use as insecticides. ;
Cenam phthalamide derivatives showing an action as insecticide are already known (cf. EP-A 0 919 542, WO 01/00575, JP-A 2001-64268, EP-A 1 006 107, JP-A 2003-40864, WO 01/21576 and WO 03/11028). Further, it is already knov/n that certain phthalamide derivatives show an action as pharmaceutical (cf. EP-A 0 119 428).
The conventional phthalamide derivatives, however, axe not fully satisfactory in terms of effects as insecticide.
There have now been found novel phthalamide derivatives of the following formula (I)
(Formula Removed)
wherein
X represents hydrogen, halogen, C1-C6~alkyl, C1-C6-haloalkyl, nitro, cyano, C1-C6-alkyl-
sulfonyioxy, C1-C6-haloalkylsulfonyloxy, phenylsulfonyloxy, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-alkylsulfonylamino, bis(C1-C6-alkylsulfonyl)amino or C1-C6-alkylcarbonyloxy,
n represents 1, 2, 3 or 4,
Y represents hydrogen, halogen, C1-C6alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy,
C1-C6-aikylthio. C1-C6baloalkylthio or cyano,
rn represents 1, 2, 3 or 4,
R represents C1-C6-alkyl, C1-C8-alkyl which is mono- or poly-substituted by substituents se-
lected from the group consisting of cyano, nitro, C1-C6-alkylarimosulfonyl, NrN-di(C1-C6-alkyl)aminosulfonyl, C1-C6-alkyIsulfonylamino, N-C1-C6-alkylsulfonyl-N-C1-C6-alkylamino, C1-C6-alkyl-carbonylamino, halo-C1-C6-alkyl, N-C1-C6-alkyl-carbonyl-N-C1-C6-alkylamino, C1-C6alkyl-thiocarbonylamino, N-C1-C6-alkylthiocarbonyl-N-C1-C6-alkylamino, C1-C6alk-oxy-imino-C1-C6alkyl, C1-C6-alkyl-aminocarboriyl, N,N-di(C1-C6-aIkyl)-aminocarbonyI, C1-C6 -alkyl-aminthiocarbonyl, N,N-di(C1-C6-alkyl)-aminothiocarbonylJ C1-C6-alkoxy-carbo-nyiammo, C1-C6-aIkoxycarbonyl-C1-C6-alkylamino. C1-C6-alkylamino-carbonyloxy'. N,N-
alkyl)aminosulfonyl, C1-C6-aIkylsulfonylamino, NrC1-C6-alkylsulfonyl-N-C1-C6-alkylamino, C1-C6-alkyl-carbonylamino, halo-C1-C6-alkyl, N-C1-C6-alkyl-carbonyl-N-C1-C6-alkylamino, C1-C6-allcyl-thiocarbonylamino, N-C1-C6-alkylthiocarbonyl-N-C1-C6-älkylarnino, C1-C6-alk-oxyimino-C1-C6-alkyl, C1-C6-alkyl-aminocarbonyl5 N5N-di(C1-C6-alkyl)-aminocaTbonyl, C1-C6-alkyl-aminotliiocarbonyl, N,N-di(C1-C6-alkyl)-aminothiocarbonyl, C1-C6-alkoxy-carbo-nylamino, C1-C6-aIkoxy-carbonyl-C1-C6-alkylamino, C1-C6-alkylarnino-carbonyloxy,

di(C1-C6-alkyl)amino-carbonyloxy, C1-C6-alkoxy-thiocarbonylamino, C1-C6-aIkoxy-thiocar-bonyl-C1-C6-alkylarniao, C1-C6-alkylammo-thiocarbonyloxy, N,N-di(C1-C6-alkyl)-amino-thiocarbonyloxy, ' C1-C6-allcylthdo-carbonylanaiao, C1-C6-alkylthio-carbonyl-C1-C6-alkyl-amino, C1-C6-aIkylamino-carbonylthio, N,N-di(C1-C6-alkyl)amino-carbonylthio, C1-C6-alkyl-thio-thiocarbonylamino, C1-C6-alkylthio-thiocarbonyl-C1-C6-alkylamino, C1-C6-alkylarnino-thiocarbonylthio, N,N-di(C1-C6-alkyl)amino-tbiocarbonylthio, C3-C6-cycloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-allcylsulfmyl-C1-C6-al]kyl and C1-C6-alkylsulfonyl-C1-C6-aIkyl, or represents C3-C8-cycloalkyl which may be substituted by substituents selected from the group consisting of C1-C4-alkyl, C1-C4-alkyItliio or C1-C2-allcyltMo-C1-C2-aUcylJ
R2 represents hydrogen or C1-C6-alkyl,
R3 represents hydrogen or C1-C6-alkyl,
A1 represents straight chain or branched chain C1-C6-aIkylene, C1-C8-haloalkylene, C2-C8-alke-nylene, C2-C8-haloalkenylene, C2-C8-alkynylene, C2-C8 -haloalkynylene, C1-C8-alkylene-amino, C1-C6-alkylene(C1-C6-alkylamino), C1-C8-alkyleneoxy or C1-C8-alkylenethio,
r represents O or l,
A2 represents straight chain or branched chain C1-C8-alkylene, C1-C8-haloalkylene, C2-C8-alke-nylene, C2-C8-haloalkenyleneJ C2-C8-alkynylene or C2-C8-haloalkynylene,
s represents O or l,
Q represents a 5- or 6-membered heterocyclic group containing l to 4 hetero atoms selected from O to 4 nitrogen atom, O to l oxygen atom, and O to l sulphur atom, however not containing an oxygen atom and a sulphur" atom at the same titne, and said heterocyclic group
may have one to three (Figure Removed), one to three (Figure Removed), one
(Figure Removed)or one
as ring constituent, and said heterocyclic group may be optionally substituted with at least one or more substituents selected from the below-mentioned group of substituents W1 wherein said substituents may be identical or different,
W1 represents halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-allcylsulfinyl3 C1-C6-alkylsulfonyl, C1-C6-haloalkyl, C1-C6-haloalkoxy, C1-C6-haloalkyltiiio, C1-C6-haloalkylsulfunyl, C1-C6-haloalkylsulfonyl, C3-C6-cycloalkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkylsul-fmyl-C1-C6-alkyl C1-C6-alkylsulfonyl-C1-C6-alkyl,
E represents phenyl, biphenyl, naphthyl, pyridyl, pyridazidnyl, pyrimidinyl, pyrazmyl, thienyl, furyl or pyrrolyl, wherein said group is optionally mono- or poly-substituted by substituents selected from the group W2 wherein said substituents may be identical or different,
W2 represents halogen, nitro, C1-C6-alkyl, C1-C-alkoxy, C1-C-alkylthio, C1-C6-alkylsulfinyl, Q-Cs-alkylsulfonyl, C1-C6-haloallcyl, C1-C6-haloalkoxy, C1-C6-haloalkylthio, C1-C6-haloalkyl-sulfinyl, C1-C6-haloalkylsulfonyl, C3-C6-cycloalkyl, C1-C6-alkylthio-C1-C6alkyl, C1-C6-al-

kylsulfinyl-C1-C6-alkyl or C1-C6alkylsulfonyl-C1-C6-alkyl, or represents C1-C6-alkylene, C3-C6-haloalkylene, oxy-C2-C4-aliylene, oxy-C2-C4-haloalkylene, C2-C4-alkyleneoxy, C2-C4-haloalkyleneoxy, C1-C3-alkylenedioxy or C1-C3-haloalkylenedioxy, in case that W2 are two adjacent substituents.
Depending, if appropriate, on the type and number of substituents, the compounds of the formula (I) can be present as geometncal and/or optical isomers, regioisomers and/or configurational isomers or isomer mixtures thereof of varying composition. What is claimed by the invention are both the pure isomers and the isomer mixtures.
The compounds of the formula (I) of the present invention can be obtained, for example, by the following preparation processes (a), (b), (c), (d), (e) and (f):
Preparation process (a): in case that R2 in the formula (I) represents hydrogen. A process of reacting compounds of the formula (II)
(Figure Removed)wherein R1, X and n have the same definition as aforementioned, with compounds of the formula (IH)
(Figure Removed)wherein R3, Y, m, A1, r, Q, A2, s and E liave Üie same definition as aforementioned., in the presence of inert solvents.
Preparation process (b): in case that R3 in the formula (I) represents hydrogen atom. A process of reacting compounds of the formula (TV) .0
(Figure Removed)wherein X, n, Y, m, A1, r, Q, A2, s and E have the same definition as •aforementioned, with compounds of the formula (V) R1
(Figure Removed)wherein R1 and R2 have the same definition as aforementioned,
in the presence of inert solvents, and if appropnate, in the presence of a base.
Preparation process (c):
A process of reacting a compound represented by the formula (VT)

(Figure Removed)wherein X, n, R1 and R2 have the same definition as aforementioned, with the compounds of the-formula (IH),

(Figure Removed)wherein R3, Y, m, A1, r, Q, A2, s and E have Ihe same definition as aforementioned, in the presence of inert solvents.
Preparation process (d): in case that R3 in the formula (I) represents hydrogen atom. A process of reacting compounds of the formula (VE)
(Figure Removed)wherein X, n, Y, m, A1, r, Q, A2, s and E have the same definition as aforementioned, with the compounds of the formula (V),
(Figure Removed)wherein R] and R2 have the same definition as aforementioned, in the presence of inert solvents.
Preparation process (e):
A process of reacting a compounds of the formula (VHT)

(Figure Removed)

wherein X, n, R3, Y, m, A1, r, Q, A2, s and E have the same definition as aforementioned, with the compounds of the formula (V),
(Figure Removed)wherein R1 and R2 have the same definition as aforementioned, in the presence of inert solvents.
Preparation process (f): in case that R1 in the formula (I) represents C1-C6-alkylsulfmyl-C1-C6-alkyl or C1-C6-alkylsulfonyl-CrC5-aIkyl. A process of reacting compounds of the formula (Ii)

(Figure Removed)wherein Rlf represents C1-C6-alkylmio-Ci-O6-alkvl, and
X, n, R2, R3, Y, m, A1, r, Q, A2, s and E have the same definition as aforementioned,
with an oxidizing agent in the presence of inert solvents.
According to the present invention, Üie phthalamide derivatives of the aforementioned formula (I) show strong insecticidal action.
The formula (I) provides a general definition of the phthalamide derivatives according to the invention.
Preferred substituents or ranges of radicals listed in the formulae mentioned above and below are illustrated below:
X preferably represents hydrogen, halogen, C1-C4-alkyl, C1-C4haloalkyl, nitro, cyano, C1-C4-aücylsulfonyloxy, C1-C4-haloalkylsulfonyloxy, phenylsulfonyloxy,

alkyl, C1-C4-alkylsulfmyl-C1-C4-alkylJ C1-C4-alkylsulfonyl-C1-C4-alkyl, C1-C4-alkylsulfonyl-amino, bis(C1-C4-alkylsulfonyl)amino or C1-C4-alkylcarbonyloxy.
X particularlv preferably represents hydrogen, fluorine, chlorine, bromine, iodine, rnethyl,
ethyl, n- or iso-propyl, n-, see-, iso- or tert-buryl, trifluoromethyl, difluoromethyl, dichloro-
fluoromethyl, trichloromethyl, nitro, cyano, methylsulfonyloxy, ethylsulfonyloxy, trifluoro-
methylsulfonyloxy, phenylsulfonyloxy, methylthiomethyl, methylthioethyl, ethylthiomethyl,
ethylüiioethyl, me&ylsulfinylmethyl, methylsulfinylethyl, ethylsulftnylmethyl, ethyl-
• sulfinylethyl, memylsulfonyhnethyl, methylsulfonylethyl, ethylsulfonylmethyl, ethylsulfo-
nylethyl, methylsulfonylamino, ethylsulfonylamino, di(methylsulfonyl)amino, di(ethylsulfo-
nyl)amino, methylcarborryloxy or ethylcarbonyloxy.
X very particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, tert-buryl, trifluoromethyl, nitro, cyano, methylsulfonyloxy, ethylsulfonyloxy, trifluoro-methylsulfonyloxy, phenylsulfonyloxy, methylsulfonylamino, di(methylsulfonyl)amino or methylcarbonyloxy.

n preferably represents l, 2 or 4.
n particularlv preferably represents 1.
n furthermore, particularlv preferablv represents 2. •
n furthermore, particularly preferablv represents 4.
Y preferably represents hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-aIkyltnio, C1-C4-haloalkylthio or cyano.
Y particularlv preferablv represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n- or iso-propyl, n-, see-, iso- or tert-butyl, trifluoromethyl, difluoromethyl, dichlorofluoromethyl, trichloromethyl, methoxy, ethoxy, n- or iso-propoxy, n-, see-, iso- or tert-butoxy, trifluoromethoxy, methylthio, ethylthio, n- or iso-propylthio, n-, see-, iso- or tert-butylthio, trifluoromethylthio or cyano.
Y very particularly preferably represents hydrogen, chlorine, methyl, trifluoromethyl, methoxy or trifluoromethoxy.
m preferably represents l or 2.
m particularlv preferablv represents 1.
m furthermore, particularlv preferablv represents 2.
R1 preferably represents C1-C6-alkyl, C1-C6-aIkyl which is mono- or poly-sübstituted by substi-tuents selected from the group consisting of cyano, nitro, C1-C4-aUcylammosulfonyl, N,N-di(C1-C4-alkyl)aminosulfonyl, C1-C4-alkylsulfonylamino,

kylamino, C1-C4-alkyl-carbonylarnino, halo-C1-C4-alkyl, N-C1-C4-alkyl-carbonyl-N-C1-C4-alkylamino, C1-C4-alkyl-tMocarbonylamino, N-C1-C4-alkylfhiocafbonyl-N-C1-C4-alkyl-amino, C1-C4-alkoxyimino-C1-C4-alkyl, C1-C4-alkyl-ainmocarbonyl3 N,N-di(C1-C4-alkyl)-aminocarbonyl, C1-C4-alkyl-ainniothiocarbonyl3 N-di(C1-C4-alkyl)-aminothiocarbonyl, C1-C4-alkoxy-carbonylamino3 C1-C4-alkoxy-carbonyl-C1-C4-alkylamino, C1-C4-alkylaraino-car-bonyloxy, N,N-di(C1-C4-alkyl)araino-cärbonyloxy3 C1-C4-alkoxy-fhiocarbonylamino) C1-C4-alkoxy-tlxiocarbonyI-C1-C4-alkylamino3 C]-C/)-alkylamino-thiocarbonyloxy, N,N-di(C1-C4-alkyl)aniino-thiocarbonyloxy, C1-C4-aIkylthio-carbonylaminoJ C1-C4alkyltliio-carbonyl-C1-C4-alkylamino, C1-C4-alkylaniino-carbonylthio) N,N-di(C1-C4-alkyl)arnino-carbonyl C1-C4-alkylthio-thiocarbonylamino3 C1-C4-allcylthio-1;hiocarbonyl-C1-C4-alkylaniino3 C1-C4-al-kylamino-thiocarbonylthio, N,N-di(C! -C4-alkyl)amiQO-fhiocarbonylthio3 C3-C6-cycloaIkyl3 C1-C4-alkoxy-C1-C4-alkyl, C1-C4-allcylthio-C1-C4-alkyI3 C1-C4-alkylsulfinyl-C1-C4-alkyl and C1-C4-alkylsulfonyl-C1-C4-alkyl3 or represents C3-C6-cycloalkyl which may be substituted by C1-C2-alkyl3 C1-C2-alkylthio or C1-C2-alkyltfaio-C1-C2-alkyl.
R1 particulariv preferablv represents methyl, ethyl, n- or iso-propyl, n-3 see-, iso- or tert-butyl, n-pentyl, 1-methylbutyl, 1-ethylpropyl, n-hexyl3 1,3-dimethylbutyl; methyl, ethyl, n- or iso-propyl, n-, see-, iso- or tert-butyl, each of which is mono- or poly-substituted by substituents selected from the group consisting of c}'ano, nitro, methylarninosulfonyl., ethylaminosulfonyl, • N,N-di(methyl)arninosulfonyl, N,N-di(ethyl)aminosulfonylJ methylsulfonylamino, ethylsul-fonylamino, N-methylsuUbnyl-N-methylamino, N-ethjdsulfonyl-N-methylamino, N-methyl-sulfonyl-N-ethylamino, N-ethylsulfonyl-N-ethylamino, methyl-carbonylamino, ethyl-cafbo-nylamino, trifluoromethyl, pentafluoroeth}'!, N-methyl-carbonyl-N-methylamino, methyl-thiocarbonylamino, ethyl-thiocarbonylamino, N-methylthiocarbonyl-N-methylamino, meth-oxyimino-methyl, methoxyimino-ethyl, eüaoxyimino-methyl., ethoxjdmino-ethyl, methyl-aminocarbonyl, ethyl-aminocarbonyl, N,N-di(methyl)-aminocarbonyl, N,N-di(ethyl)-amino-carbonyl, methyl-arnmothiocarbonyl, ethyl-aminothiocarbonyl, N3N-di(methyl)-aminotiiio-carbonyl, N,N-di(ethyl)-aminotliiocarboriyl., methoxy-carbonylarnino, ethoxy-carbonylamino, methoxy-carbonyl-methylamino, eüioxy-carbonyl-methylamino, methoxy-carbonyl-ethyl-amino, ethoxy-carbonyl-ethylamino, methylamino-carbonyloxy, etiiylamino-carbonyloxy, N,N-di(methyl)amino-carbonyloxy, N,N-di(ethyl)amino-carbonyloxy, methoxy-thiocarbo-nylamino, ethoxy-thiocarbonylamino, methoxy-thiocarbonyl-methylamino, methoxy-thiocar-bonyl-ethylamino, ethoxy-thiocarbonyl-methylamino, ethoxy-thiocarbonyl-ethylamino, me-thylamino-tiiiocarbonyloxy, ethylamino-thiocarbonyloxy, N,N-di(methyl)amiao-thiocarbo-nyloxy, N,N-di(ethyl)amino-thiocarbonyloxy, methylthio-carbonylamino, ethylthio-carbonyl-amino, methylthio-carbonyl-methylamino, ethylthio-carbonyl-methylamino, methylthio-car-bonyl-ethylamino, ethylthio-carbonyl-ethylamino, methylamino-carbonylthio, ethylamino-carbonylthio, N,N-di(methyl)amino-carbonylthio, N,N-di(ethyl)amino-carbonylthio., methyl-

thio-thiocarbonylamino., ethylthio-thiocarbonylamiao, methylüiio-tliiocarbonylrmethylamino, ethylfhio-tlTiocarbonyl-methylamino, methylthio-thiocarbonyl-ethylainino, ethylthio-thiocar-bonyl-ethylarnino, methylamino-thiocarbonylthio, ethylamino-fhiocarbonylthio, N,N-di(me-thyl)amino-thiocarbonyithio, N,N-di(methyl)aimno-ti:tiocarbonylthio, cyclopropyl, cyclopen-tyl, cyclohexyl, metiioxy-methyl, ethoxy-methyl, methoxy-ethyl, ethoxy-ethyl, methyltbio-methyl, ethylthio-methyl, methylthio-ethyl, ethylthio-ethyl, methylsulfinyl-methyl, ethylsulfi-nyl-methyl, methylsulfinyl-ethyl, ethylsulfinyl-ethyl, methylsulfonyl-methyl, ethylsulfonyl-methyl, methylsulfonyl-ethyl, and ethylsulfonyl-ethyl; or represents cyclopropyl, cyclopen-tyl, cyclohexyl., each of which may be substituted by substituents selected from the group consistmg of methyl, ethyl, methylthio, ethylthio, methylthiomethyl, ethylthiomethyl, methylthioethyl and ethyltbioethyl.
R1 very particularly preferably represents methyl, ethyl, n- or iso-propyl, n- or sec-buryl, n-pentyl, 1-methylbutyl, 1-ethylpropyl, 1,3-dimethylbutyl; methyl, ethyl, n- or iso-propyl, n-, see-, iso- or tert-butyl, each of which is mono- or poly-substituted by substituents selected from the group consisting of cyano, methylaminosulfonyl., ethylaminosulfonyl, N,N-di-
(meth}'l)aminosulfonyl, N,N-di(ethyl)aminosulfonyls N-methylsulfonyl-N-methylammo, me-thyl-carbonylamino, trifluoromethyl, pentafliaoroethyl, methoxyimino-methyl, methoxy-imino-ethyl, ethoxyimino-methyl, ethoxyimino-ethyl, methyl-aminocarbonyl, ethyl-amino-carbonyl, N5N-di(methyl)-aminocarbonyl, N,N-di(ethyl)-aminocarbonyl, methyl-aminothio-carbonyl, ethyl-aminothiocarbonyl, N,N-di(rn.ethyl)-aminothiocarbonyl5 N,N-di(ethyl)-ami-nothiocarbonyl, methoxy-carbonylamino, methylarnino-carbonyloxy, ethylamino-carbonyl-oxy, N,N-di(methyl)arnino-carbonyloxy, N,N-di(ethyl)amino-carbonyloxy, methylamino-thiocarbonyloxy, N,N-di(methyl)amino-thiocarbonyloxy, metitylammo-carbonylthio, ethyl-amino-carbonylüiio, methylaniino-thiocarbonylthio, eüiylamino-tliiocarbonylthio, cyclohexyl, methoxy-methyl, ethoxy-methyl3 methylthio-methyl, methylsulfinyl-methyl and methylsulfonyl-methyl; or cyclopropyl, cyclopenlyl, cyclohexyl, each of which may be substituted by substituents selected from the group consisting of methyl, methylthio and metliyl-thiomethyl.
R2 preferably represents hydrogen or C1-C4-alkyl.
R2 particularlv preferablv represents hydrogen, methyl or ethyl.
R2 yery particularly preferably represents hydrogen or ethyl.
R3 preferably represents hydrogen or C1-C4-alkyl.
R3 particularlv preferablv represents hydrogen, methyl, ethyl, n- or iso-propyl.
R3 very particularly preferably represents hydrogen, methyl, ethyl or iso-propyl.

A1 preferably represents straigbt chain or branched chain C1-C6-alkylene, C1-C6-haloalkylene, C2-C6-alkenylene, C2-C6-haloalkenylene, C2-C6-alkynylene3 C2-C6-haloalkynylene., C1-C6-al-kylene-amino, C1-C6-altylene(C1-C4-alkylamino), C1-C6-alkyleneoxy or C1-C6-alkylenethio.
A1 particularlv oreferablv represents -CH2-, -(CH2)2-3 -(CH2)3-, -CH(CH3)-3 -OCH2-, -CH20.-, -O(CH2)2-, -(CH2)2O-3 -SCH2-3 -CH2S-3 -S(CH2)2- or-(CH2)2S-.
A1 very particularly preferably represents -CH2-, -(CH2)2-3 -CH(CH3)-, -OCH2-, -O(CH2)2- or -CH2S-.
r preferably represents 0.
r furthermore preferably represents l.
A2 preferably represents straight chain or branched chain C1-C6-alkylene, C1-C6-haloaIkylene5
C2-C6-alkenylene, C1-C-haloalkenylene, C2-C6-aIkynylene or C2-C6-haloall Tiylene. A2 tiarticularlv preferablv represents -CH2-, -(CH2)2-3 -(CH2)3-3 -CH(CH3)-3 -CH2-CH=CH-.
s preferably represents 0.
s furthermore. preferably represents 1.
Q preferably represents pyridinylene, pyridazinylene, pyrirnidinylene, pyrazinylene, each of which is optionally mono- or poly-substituted by substituents selected frorn group W1 wherein said substituents may be identical or different, or further represents the below-mentioned groups;
(Figure Removed) (Avherein the bond märked with * connects with A1 and the bond märked with # connects
with A2, or the bond märked with # connects with A1 and the bond märked with * connects
withA2) Q particularlv preferablv represents Q15, Q17, Q22, Q23, Q29, Q34, Q35, Q45, Q4S, Q50,
Q55, Q56, Q58, Q59, Q60, Q61, Q62, Q63, Q64, Q66 and Q69. Q very particularly preferably represents Q15. Q furthermore very particularly preferably represents Q17. Q furthermore very particularly preferably represents Q22. Q furthermore very particularly preferably represents Q23. Q furthermore very particularly preferably represents Q29. Q furthermore very particularly preferably represents Q34. Q furthermore very particularly preferably represents Q35. Q furthermore very particularly preferably represents Q45. Q furthermore very particularly preferably represents Q48. Q furthermore very particularly preferably represents Q50.

Q- furthermore very particularly preferably represents Q55.
Q furthermore very parücularly preferably represents Q56.
Q furthermore very particularly preferably represents Q5 8.
Q furthermore very particularly preferably represents Q59.
Q furthermore very particularly preferably represents Q60.
Q furthermore very particularly preferably represents Q61.
Q furthermore very particularly preferably represents Q62.
Q furthermore very particularly preferably represents Q63.
Q furthermore very particularly preferably represents Q64.
Q furthermore very particularly preferably represents Q66.
Q furthermore very particularly preferably represents Q69.
W1 preferably represents halogen, C1-C4-alkyl, C1-C4-alkoxy5 C1-C4-alleylthio, C1-C4-alkylsulfrnyl, C1-C4-alkylsulfonyl, C1-C4-haloalkyl, C1-C4-haloaIkoxy, C1-C4haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloalkylsulfonyl, C3-C6-cycloalkyl, C1-C4-alkylthio-C1-C4-
alkyl, C1-C4-alkylsulfinyl-C1-C4-alkyl, C1-C4-alkylsulfonyl-C1-C4-alb>d. W1 particularlv preferablv represents methyl, ethyl, methoxy, methylthio, memylsulfmyl or
methylsulfonyl. W1 very particularly preferably represents methyl.
E preferably represents phenyl, biphenyl, naphthyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, thienyl, furyl or p)Trolyl, wherein said group is optionally mono- or poly-substituted by sub-stituents selected from the group W2 wherein said substituents may be identical or different.
E particularlv preferablv represents phenyl, biphenyl, 3-pyridyl, 2-thienyl, 2-furyl or 2-pyrrolyl,
wherein said group is optionally mono- to tetra-substituted by substituents selected from the group W2 wherein said substituents may be identical or different.
E very particularly preferably represents phenyl, biphenyl, 3-pyridyl or 2-thienyl, wherein said
group is optionally mono- to tetra-substituted by substituents selected from the group W2 wherein said substituents may be identical or different.
W2 preferably represents halogen, nitro, C1-C4-alkyl, C1-C4alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloallcyl, C1-C4haloalkoxy, C1-C4-haloalkylthio, C1-C4-haloalkylsulfinyl, C1-C4-haloaUcylsulfonyl, C3-C6-cycloalkyl, C1-C4alkylthio-C1-C4 alkyl, C1-C4-alkylsulfinyl-C1-C4-allcyl or C1-C4-allcylsulfonyl-C1-C4-allcyl, or represents C3-C5-alkylene, C3-C5-haloalkylene, oxy-C2-C4-alkylene, oxy-C2-C4-haloallcylene, C2-C4-alky-leneoxy, C2-C4-haloalkyleneoxy, C1-C3-alkylenedioxy or C1-C3-haloaIkylenedioxy, in case W2 are two adjacent substituents.

W2 particularlv preferablv represents fluorine, chlorine, bromine, nitro, methyl., ethyl, n- or iso-propyl, n-, see-, iso- or tert-butyl, methoxy, ethoxy, n- or iso-propoxy, n-, see-, iso- or tert-butoxy, trifluoromethoxy, diiluorometlloxy, methylthio, ethylthio, n- or iso-propylthio, n-, see-, iso- or tert-butylthio, trifiuoromethyl, difluoromethyl, dichlorofiuoromethyl, trichloro-methyl, trifluoromethoxy, difluoroniethoxy, trifluoromethylthio, or represents -OCF2O, -0(CF2)2O-, -OCHFCF20-, -OCF2CHFO-, in case W2 are two adjacent substituents. - W2 very particularly preferably represents fluorine, chlorine, bromine, nitro, methyl, ethyl, iso-propyl, methoxy, trifluorornethoxy, difluoromethoxy, methylthio, trifluoromethylthio, or represents -OCF2O~, -O(CF2)2O-, -OCHFCF20-, -OCF2CHFO-, in case W2 are two adjacent substituents.
W3 represents hydrogen or has the same definition as the aforementioned W1, W3 preferably represents hydrogen, rnethyl, trifluoromethyl or methylthio.
p represents O, l or 2. -
P preferably represents 0.
p furthermore preferably represents 1.
q represents O, l, 2 or 3.
q preferably represents 0.
q furthermore preferably represents l.
Compounds of formula (T), in which r is O and s is O are preferred.
Compounds of formula (I), in which r is l and s is l are preferred.
Compounds of formula 00, in which r is l and s is O are particularly preferred.
Compounds of formula (I), in which R2 and R3 are both hydrogen are preferred.
Compounds of formula (T), in which n is l and X is located in 3-position are preferred.
Compounds of formula (I), in which X is iodine are preferred.
Compounds of formula (T), in which Y is methyl are preferred.
Compounds of formula (T), in which A1 is -CH2- are preferred.
Compounds of formula (I), in which E is mono- to tetra-substituted phenyl, where the substituents are
selected firom the group W2, are preferred.
Compounds of formula (T), in which Q is Q66 are preferred.
The general or preferred radical definitions or illustrations h'sted above apply both to the end products and, correspondingly, to the starting materials and intermediates. These radical definitions can be

combined with one another as desired, i.e. including combinations between the respective preferred ranges.
Preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being preferred.
Particular preference according to the invention is given to the compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred.
Very particular preference according to the invention is given to the compounds of the formula (T) which contain a combination of the meanings listed above as being very particularly preferred,
In the radical defmitions given above and below, carbon radicals, such as alkyl, are in each case straight-chain or branched as far as this is possible - including in combination with hetero atoms such as alkoxy.
The aforementioned preparation process (a) can be illustrated by the following reaction scheme in
case, for example, that 3-(l,l-dirnethyl-2- memylthioemylimino)-4-iodo-3H-isobenzofuran-l-one and
l-(4-amino-3-methylbenzyl)- 4-(4-trifiuoromethylphenyl)-l,4-dihydrotetrazol-5-one are used as
startingmaterials.
(Figure Removed)The aforementioned preparation process (b) can be illustrated by the following reaction scheme in case, for example, that 2-{2-methyl-4-[5-oxo-4-(4-trifluorometh.ylphenyl)-4,5-dihydrotetrazol-l-yl-methyl]phenyl}isoindole-l.,3-dione and sec-butylamine are used as starting materials.
(Figure Removed)The aforementioned preparation process (c) can be illustrated by the following reaction scheme in case, for example, that N-(l-methyl-propyl)phthalamic acid and i-(4-amino-3-metrrylbenzyl)-4-(4-trifiuoromethylphenyl)-l,4-dihydrotetra2ol-5-one are used as starting materials. (Figure Removed)The aforementioned preparation process (d) can be.illustrated by the following reaction scheme in case, for example, that l-[4-(3-oxo-3H-isobenzoflu:an-l-ylideneamino)-3-rnetliyl-benzyl]-4-(4-tri-fluoromethyl-phen3'l)-l,4-dihydrotetrazol-5-one and sec-butylarnine are used as starting materials. P
The aforementioned preparation process (e) can be illustrated by the following reaction scheme in case, for example, thatN-{2-methyl-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-4,5rdihydro-tetrazol-l-yl-methyl]-phenyl}-phthalamic acid and sec-butylamine are used as starting materials. OH

The aforementioned preparation process (f) can be Illustrated by the following reaction scheme in case, for example, that N2-(l3l-dimethyl-2-methylthioethyl)-3-iodo-N1-[2-methyl-4-(5-oxo-4-(4-tri-iluorometlaylphenyl)-4,5-dihydro-tetrazol-l-ylmet:hyl)-phenyl]-phthalamide and m-chloroperbenzoic acid are used as starting materials.
(Figure Removed)The compounds of the formula (ü), starting material in the above-mentioned preparation process (a), are per se known compounds and can be easily prepared according to the process described in, for example, EP-A O 919 542, EP-A l 006 107.
As specific examples of the compounds of the formula (ü) used as starting material in the preparation process (a) there can be mentioned the following: 3-isopropylimino-3H-isobenzofuran-1-one,
4-fiuoro-3-isopropyliirrmo-3H-isobenzofuran-l-one,
4-cbloro-3-isopropylimino-3H-isobenzofuran-l-oiie3
4-bromo-3-isopropylimino-3H-isobenzofuran-1 -one,
4-iodo-3-isopröpyliaiino-SH-isobenzoiuran-1-one3
3-isopropylirnino-4-nitro-3H-isobenzožuran-1 -one,
3-isopropylimmo-5-nitro-3H-isobenzofuran-l-one,
3-(l -methyl-2-methylsiilfanyl-etb.ylimino)-3H-isobenzofuran-1 -one,
4-fluoro-3-(l-methyl-2-meth}'lsulfanyl-ethylimino)-3H-isobenzofuran-l-one,
4-chloro-3 -(l -methyl-2-methylsulfanyl-ethylimino)-3H-isobenzofuran-1 -one,
4-bromo-3-(l-methyl-2-methylsulfanyl-ethyliiriino)-3H-isobenzofln:an-l-one,
4-iodo-3-(l -methyl-2-methylsulfanyl-ethylimino)-3H-isobenzoiuran-1 -one,
3 -(l -met3iyl-2-methylsulfanyl-ethylimino)-4-nitro-3H-isobenzoiuran-1 -one,
3-(l, l -dime1±iyI-2-meth)dsulfanyl-ethylimino)-3H-isobenzofuran-1 -one,
3-( l, l -dimethyl-2-methylsulfanyl-ethylirnino)-4-fluoro-3H-isobenzofuran-1 -one,
4-chloro-3-( l, l -dimethyl-2-methylsulfanyl-e1hyliniino)-3H-isobenzofaran-1 -one,
4-bromo-3 -(1,1 -dimethyl-2-methylsulfanyl-ethylimino)-3H-isobenzofuran-1 -one,
3-( l, l -methyl-methithylsulfanyl-ethyliminol-iodo-SH-isobenzofuran-1 -one,
3-(l,l-dÜTiethyl-2-methylsulfanyl-et3b.ylijnino)-4-rdtro-3H-isoben2ofiiran-l-one3
3-( l, l -dimethyl-2-methylsulfanyl-ethyliinmo)-4-methyl-3H-isobenzofuran-1 -one,
3-(l,l-methyl-2-methylsidfanyl-ethylmino)-5-methyl-3H-isobenzofuran-l-one,
4,7-dicKloro-3-(l,l-dimethyl-2-methylsulfanyl-eÜiyliriiino)-3H-isobenzofuran-l-one,
5,6-dichloro-3 -(1,1 -dimethyl-2-methylsulfanyl-ethylirnino)-3H-isobenzofuran-1 -one,
4,5,6,7-te1racbJoro-3-(l,l-dimethyl-2-me1hylsdfanyl-aylimino)-3H-isobenzofuran- l-one,
3-isopropylinoino-l-oxo-l,3-dihydro-isobensoiui'an-4--ylmethanesulfonate,
3 -(l -methyl-2-methylsulfanyl-etliyliniino-1 -oxo-1,3 -dihydro-isobenzofiiran-4-yl methanesulfonate,
3 -(l, l -dimethyl-2-methylsulfanyl-etliylimino-1 -oxo-1,3 -dihydro-isobenzofuran-4-yl
methanesulfonate.
The compounds of the formula (UI), starting material in the above-mentioned preparation process (a), include novel compounds not mentioned in the existing literatui"e as a part.
Their corresponding anilines can be obtained, for example, by a catalytic hydrogen reduction, a well-known process in the field of organic chemistry, by reduciag compounds of the formula
(Figure Removed)wherein Y, m, A1, r, Q, A2, s and E have the same definitions as aforementioned
with hydrogen in the presence of a catalytic reduction catalyst, for example, palladium carbon, Raney nickel, platinum oxide.
Compounds of the formula (HT), in which R3 corresponds alkyl, can be obtained by formylating the amino group of the anilines, further alkylating and then de-formylating. Moreover, compounds of the formula (UI), in which R3 corresponds alkyl, can also be obtained by preparing a Schiff base complex by a reaction of the anilines obtained by the reduction of compounds of the formula (DQ and a ketone or an aldehyde and then by catalytically reducing it.
The compounds of the above-mentioned formula (IX) are, as will be described later in detail, novel compounds.
As specific examples of the compounds of the formula (IH) there can be mentioned, for example,
l -(4-amino-3-methyl-benzyl)- IH-pyrazole,
l -(4-amino-3-methyl-benzyl)-3-methyl- IH-pyrazole,
l -(4-arnino-3-methyl-benzyl)-4-methyl- IH-pyrazole.,
l-(4-amino-3-methyl-benzyl)-4,5-dichloro-lH-imidazole.,
l-(4-amino-3-methyl-benzyl)-lH-l,2,3-triazole,
l -(4-amino-3-methyl-benzyl)- 1H-1,2,4-triazole,
l-(4-amino-3-methyl-benzyl)-lH-tetrazole,
l-(4-amino-3-methyl-benzyl)-5-methyl-lH-tetrazole,
l-(4-amino-3-methyl-benz)4)-5-(2-chloro-phenyl)-lH-tetrazole3
l-(4-ammo-3-me1iyl-benzyl)-5-(3-trifluoromethyl-phenyl)-lH-tetrazole,
l-(4-amino-3-methyl-benzyl)-5-(4-trifluoromethyl-phenyl)-lH-tetrazole,
l-(4-amino-3-methyl-benzyl)-5-(3,5-bis-trifluoromethyl-phenyl)-lH-tetrazole,
l-(4-amino-3-methyl-benzyl)-5-(3-trifluoromethoxy-phenyl)-lH-tetrazole.,
l-(4-arnino-3-methyl-berrzyl)-3-(4-1rifluoromethyl-phenyl)-iniidazolydin-2-one,
l-(4-amino-3-methyl-benzyl)-3-(4-trifluoromethyl-phenyl)-l,3-dihydro-iinidazol-2-one,
!-(4-amino-3-m.etliyl-beiTzyl)-3-(4-1rifluoromethyl-phenyl)-irnidazolydin-2,4-dione3
l-(4-ammo-3-methyl-benzyl)-3-(4-trifluoromemyl-phenyl)-irnidazolydin-2,435-trione,
l-(4-aniino-3-methyl-benzyl)-3-(4-triflüoromethyl-phenyl)-lH-pyrazole] .
4-(4-amino-3-methyl-benzyl)-2-(2-fluoro-phenyl)-2,4-dihydro-l,2,4-triazol-3-one,
4-(4-ammo-3-methyl-benzyl)-2-(2-chloro-phenyl)-2,4-dihydro-l52,4-triazol-3-one,
4-(4-amino-3-methyl-benzyl)-2-(2-trifluororüethyl-phenyl)-2,4-diliydro-1,2,4-triazol-3 -one,
4-(4-amino-3-methyl-benzyl)-2-(3-fluoro-phenyl)-2,4-dihydro-l,2,4-triazol-3-one,
4-(4-amino-3-methyl-benzyl)-2-(3 -chloro-phenyl)-2,4-dihydro-1,2,4-triazol-3 -one,
4-(4-ammo-3-metiyl-benzyl)-2-(3-trifluoromethyl-phenyl)-2,4-dihydro-l,2,4-triazol-3-one
2-(4-fluoro-phenyl)-4-(4-amino-3-methyl-benzyl)-2,4-dihydro-l32,4-triazol-3-one3 . 4-(4-amino-3-methyl-benzyl)-2-(4-chIoro-phenyl)-2,4-diliydro-l.,2.,4-triazol-3-oneJ-4-(4-amino-3 -methyl-benzyl)-2-(4-trifluorometh.yl-phenyl)-2,4-dihydro-1,2,4-triazol-3 -one, 4-(4-ammo-3-methyl-benzyl)-2-(3,4-bis-trifluoromethyl-phenyl)-2,4-dihydro-l,2,4-triazol-3-one, • 4-(4-amino-3-methyl-benzyl)-2-(3,5-bis-tri£luoromethyl-phenyl)-2,4-dihydro-l,2,4-triazol-3-oneJ 4-(4-ainino-3-methyl-beil)-5-trifluoromethyl-2-(4-Mfluoromethyl-phenyl)-2;4-dihydro-l3234 triazol-3-one,
2-(4-amino-3-methyl-benzyl)-4-(2-chloro-phenyl)-234-dihydro-l,234-triazoi-3-one3 2-(4-arnino-3-methyl-benzyl)-4-(4-trifl
2-(4-airidno-3-methyl-benzyl)-5-methyl-4-(4-trifluoromethyj-phenyl)-234-dihyd2-(4-amino-3-methyl-benzyl)-4-(2-cUoro-phenyl)-5-methylsulfanyl-2J4-dihydro-lf2,4-triazol-3-one3 2-(4-amino-3-methyl-benzyl)-5-methylsulfanyl-4-(4-trifluoromethyl-phenyl)-234-dihydro-l32,4-triazol-3-one,
l-(4-amiao-3-methyl-benzyl)-4-methyl-l34-dihydro-tetrazol-5-one3 l -(4-amino-3 -methyl-benzyl)-4-ethyl-134-dihydro-tetrazol-5-one, l-(4-amino-3-methyl-benzyl)-4-propyl-l34-dihydro-tetrazol-5-one3 l -(4-amino-3-methyl-benzyl)-4-isobu1yl-1,4-düiydro-tetrazol-5-one3 l -(4-amino-3-methyl-benzyl)-4-(232,2-trifluoro-ethyl)-134-dihydro-tetrazoI-5-one3 l-(4-amino-3-methyl-benzyl)-4-(4,434-trifluoro-butyl)-l,4-düiydro-tetrazol-5-one3 l-(4-ämino-3-methyl-benzyl)-4-(33333-trichloro-2-methyl-propyl)-l34-dihydro-tetrazol-5-one3 l-(4-arnino-3-metihiyl-benzyl)-4-cyclopropyl-l34-dihydro-tetrazol-5-one3 l -(4-amino-3 -methyl-benzyl)-4-cyclohexyl-1,4-düiydro-tetrazol-5-one5 l-(4-amino-3-methyl-benzyl)-4-phenyl-l34-dihydro-tetrazol-5-one3 l -(4-amino-3-methyl-benzyl)-4-(2-fluoro-phenyl)-1,4-diliydro-tetrazol-5-one, l -(4-amino-benzyl)-4-(2-chloro-phenyl)-134-dihydro-tetrazol-5-one, l-(4-amino-3-methyl-benzyl)-4-(2-chloro-phenyl)-l34-dihydro-tetrazol-5-one3 l-[l-(4-amino-3-methyl-phenyl)-ethyl]-4-(2-chloro-pb.enyl)-l34-dib.ydro-tetrazol-5-one, l -(4-amino-3-metliyl-benzyl)-4-(2-methyl-phenyl)-134-dihydro-tetrazol-5-one, l -(4-amino-3-meth.yl-benzyl)-4-(2-methoxy-phenyl)-1,4-dihydro-tetrazol-5-one3 l -(4-amino-3-methyl-benzyl)-4-(2-trifluoroinetiiyl-phenyl)-134-dihydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyl)-4-(2-trifluoromethoxy-phenyl)-l34-dib.ydro-tetrazol-5-one., l-(4-amino-3-methyl-benzyl)-4-(3-fluoro-phenyl)-l34-dihydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyI)-4-(3-chloro-phenyl)-l34-dihydro-tetrazol-5-one3 l -(4-amino-3-methyl-benzyl)-4-(3 -methyl-phenyl)-134-dihydro-tetrazol-5-one., l-(4-amino-benzyl)-4-(3-trifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one3 l -(4-amino-3-methyl-benzyl)-4-(3 -trifluoromethyl-phenyl)-134-dihydro-tetrazol-5-one., l-(4-amino-3-meth.yl-benzyl)-4-(3-difluorometlioxy-phenyl)-l34-dihydro-tetrazol-5-one.,

l-(4-amino-3-methyl-benzyl)-4-(3-1iifluoromethoxy-phenyl)-l]4-diliydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyl)-4-(4-fluoro-phenyl)-l34-dihydro-tetrazol-5-one, l-(4-amino-3-methyl-benzyl)-4-(4-chloro-phenyl)-l,4-dihydro-tetrazol-5-one3 l -(4-amino-3 -methyl-benzyl)-4-(4-bromo-phenyl)-1,4-dihydro-tetrazol-5 -one, l-(4-amino-3-meth}4-benzyl)-4-(4-methyl-phenyl)-lJ4-dihydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyl)-4-(4-isopropyl-phenyl)-l;4-dihydro-tetrazol-5-one3 l-(4-amino-benzyl4)-4-(4-trifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one3 l-(4-amino-2-chloro-benzyl)-4-(4-trifluorornethyl-phenyl)-l34-dthydro-tetrazol-5-one3 „ l-(4-amino-3-cliloro-benz3'l)-4-(4-1rifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one, l-(4-amino-3-methyl-benzyl)-4-(4-trifluoromethyl-phenyl)-lJ4-dihydro-tetrazol-5-one3 l -(4-atnino-3 -methyl-benzyl)-4-(4-difluoromethoxy-pb.enyl)-134-dihydro-tetrazol-5 -one, l-(4-aniino-3-methyl-beii254)-4-(4-trifluoromethoxy-phenyl)-l,4-dihydro-tetrazol-5-one3 l-(4-amino-3-methyl-benzyl)-4-(4-trifluorome1žiylsulfanyl-phenyl)-l34-dihydro-tetrazol-5-one3 l-(4-amino-3-me1hyl-benzyl)-4-(4'-trifluoroinethyl-biphenyl-4-yl)-l34-dihydro-tetrazol-5-one3
l-(4-amino-3-me1žiyl-benzyl)-4-(3,5'-bis-trifluoromethyl-biphenyl-4-yl)-l34-dib.ydro-tetrazol-5-one3
l-(4-amino-3-methyl-benzyl)-4-(4-bromo-2-fluoro-phenyl)-l.,4-dihydro-tetrazol-5-one3
!-(4-amiiio-3-methyl-benzyl)-4-(2-fluoro-3-1rifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one.,
l -(4-amino-3-methyl-benzyl)-4-(3-bromo-4-trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one3
l-(4-amino-3-meth.yl-benzjd)-4-(3-chloro-4-trifluoromethoxy-phenyl)-lJ4-dihydro-tetrazol-5-one3
l-(4-ainino-3-methyl-benzyl-4-(4-fluoro-3-trifluoromethyl-phenyl)-l,4-dihydro-tetrazol-
!-(4-amino-3-methyl-beri2yl)-4-(2-fluoro-5-trifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-oneJ
l -(4-ammo-3-methyl-benzyl)-4-(4-chloro-3-trifluorometliyl-phenyl)-1,4-dihydro-tetrazol-5-orie,
l-(4-amino-3-methyl-benzyl)-4-(334-dicliloro-phenyl)-l34-diliydro-tetrazol-5-one.,
l -(4-amino-3-meth.yl-benzyl)-4-(3,4-bis-trifluoromethyl-phenyl)-1,4-düiydro-tetrazol-5-one3
l-(4-amino-3-methyl-benzyl)-4-(3-fluoro-5-trifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one3
l-(4-amino-3-methyl-benzyl)-4-(335-dicHoro-phenyl)-l)4-dili)'dro-tetrazol-5-one3
l -(4-amino-3-methyl-benzyl)-4-(3,5-dimethoxy-phenyl)-1,4-dihydro-tetrazol-5-one3
l-(4-armno-2-chloro-benzyl)-4-(3,5-bis-trifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one,
l-(4-amino-3-chloro-benzyl)-4-(335-bis-trifluorometh)d'-phenyl)-l34-dihydro-tetrazol-5-one,
l-(4-amino-3-methyl-benzyl)-4-(335-bis-trifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one3
l -(4-amino-2-methoxy-benzyl)-4-(3,5-bis-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5 -one,
l-(4-amino-3-methoxy-benzyl)-4-(335-bis-trifluoromethyl-phenyl)-l,4-dihydro-tetrazol-5-one,
l -(4-amino-3,5 -dimethyl-benzyl)-4-(3,5-bis-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,
l-[l-(4-ammo-3-meihyl-phenyl)-eÜiyl]-4-
l-(4-amino-3-methyl-benzyl)-4-(3-chloro-2-methoxy-5-inethyl-phenyl)-l,4-dihydro-tetrazol-5-one,
l-(4-amino-3-methyl-benzyl)-4-(2,2-difluoro-benzo[l.,3]dioxol-5-yl)-l,4-dihydro-tetrazol-5-one3

l-(4-amino-3-methyl-benzyl)-4-(2,2333-tetrafluoro-2,3-dihydro-benzo[l)4]dioxin-6-yl)-l.,4-diliydro-tetrazol-5-one,
l-(4-ammo-3-me%l-benzyl)-4-(2,233-1rifluoro-2)3-dihydro-benzo[l)4]cHoxin-6-yl)-l34-dihydro-tetrazol-5-one3
l-(4-amino-3-methyl-benzyl)-4-(2,33-trifluoro-2,3-dihydro-benzo[l54]dioxin-6-yl)-l,4-dihydro-tetrazol-5-one,
l-(4-amino-3-methyl-benzyl)-4-(22,33337-pentafluoro-233-dihydro-benzo[l,4]dioxin-6-yl)-l34-
dihydro-tetrazol-5-one,
l -(4-amino-3 -methyl-benzyl)-4-(3,5 -dichloro-2,6-diethyl-phenyl)-134-dihydro-tetrazol-5-one3
l-(4-amino-3-methyI-benzyl)-4-benzyl-l)4-dihydro-tetrazol-5-one3
l-(4-amino-3-methyl-benzyl)-4-(4-fluoro-benzyl)-l34-dihydro-tetrazol-5-one.,
l -(4-amino-3 -methyl-benzyl)-4-(4-chloro-phenyl)-1,4-dihydro-tetrazol-5-one3
l-(4-anüno-3-methyl-benzyl)-4-(4-trifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one,
l-(4-amino-3-rnethyl-benzyl)-4-[l-(2-fluoro-phenyl)ethyl]-l,4-dihydro-tetrazol-5-one3
l-(4-amino-3-methyl-benzyl)-4-[l-(2-chloro-phenyl)ethyl]-l34-dihydro-tetrazol-5-one,
l-(4-amino-3-methyl-benzyl)-4-[l-(2-trifluoromethyl-phenyl)-ethylJ-l,4-dihydro-tetrazol-5-one;
l-(4-aniino-3-methyl-benzyl)-4-l-[l-(3-fluoro-phenyl)-ethyl]-l34-dihydro-tetrazol-5-one)
l-(4-amino-3-methyl-benzyl)-4-[l-(3-chloro-phenyl)-ethyl]-l34-dihydro-tetrazol-5-one3
l -(4-amino-3-mefhyl-benzyl)-4- [ l -(3 -frifluoromethyl-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,
l-(4-amino-3-methyl-benzyl)-4-[l-(4-fluoro-phenyl)-ethyl]-l,4-dihydro-tetrazol-5-one,
l-(4-amino-3-met:hyl-benzyl)-4-[l-(4-chloro-phenyl)-ethyl]-l34-dihydro-tetrazol-5-oneJ
l-(4-amino-3-methyl-benq4)-4-[l-(4-1rifluorometh}'l-phen3'l)-ethyl]-l,4-dihydro-tetrasol-
l-(4-amino-3-methyl-benzyl)-4-[l-(234-difluoro-phenyl)-eÜiyl]-l,4-dihydro-tetrazol-5-one3
l -(4-amino-3-methyl-benzyl)-4-[l -(2,4-dichloro-phenyl)-ethyl]-134-dib.ydro-tetrazol-5-one,
l -(4-amino-3 -methyl-benzyl)-4- [ l -(3,4-diflu6ro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one.
The compounds of the formula (JV), staiting materials in the above-mentioned preparation process (b), are novel ones and can be easily obtained according to the process described in JP-A 61- 246161, for example,
by reacting a compound represented by the formula-
(Figure Removed)wherein X and n have the same definition as aforementioned, with the compounds of the aforementioned formula (TS)

(Figure Removed)

in which R represents a hydrogen atom and Y, m, A1, r, Q, A2, s and E have the same definitions as aforementioned.
The reaction can be conducted in an adequate diluent. As examples of the diluent used in that case there can be mentioned aliphatic, alicyclic and aromatic hydrocarbons (may be optionally chlori-nated), for example, pentane, hexane, cyclohexane, petroleum ether, hgroine, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, di-chlorobenzene; ethers, for example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tefrahydrofuran (THF), diethylene glycol dimethyl ether (DGM); esters, for example, ethyl acetate, amyl acetate; acid amides, for example, dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone, l,3-dimethyl-2-imidazolidinone,
hexamethyl phosphoric triamide (HMPA); acids, for example, acetic acid.
The reaction can be conducted in a substantially wide range of temperature. It can be conducted at the temperatures in a range of generally room temperature to. about 200°C, preferably room temperature to 150°C.
Although said reaction is conducted desirably under normal pressure, it can be operated also under elevated pressure or under reduced pressure.
In conducting the reaction, the aimed compounds can be obtained, for example, by reacting equimolar amount or a litile excess amount of the compounds of the formula (EH) to l mole of the compounds of the formula (X) in a diluent, for example, acetic acid.
Many of the compounds of the above-mentioned formula (X) are known (available on the marker)
compounds and as their specific examples there can be mentioned,
phthalic anhydride,
3-fluorophthalic anhydride,
3-chlorophthalic anhydride,
3-bromophthalic anhydride,
3-iodophthalic anhydride,
3-methylphthalic anhydride,
3-nitrophthalic anhydride,
3,6-difluorophthalic anhydride,

3,6-dichlorophthalic anhydride, 4,5-dichlorophthalic anhydride, 3,4,5,6-tetrafluorophthalic anhydride, 3,4,5,6-tetrachlorophthalic anhydride, 3-methanesulfonyloxyphthalic anhydride.
Among the above-mentioned examples, 3-methanesulfonyloxyphthalic anhydride can be easily obtained from 3-hydroxyphthalic anhydride and methanesulfonyl chloride according to the process described in Tetrahedron Lett., 1988, 29, 5595-5598.
Similarly the compounds of the aforementioned formula (JU), in which R3 represents a hydrogen atom, starting materials for the compounds of the formula (IV), can be easily obtained, as described in the aforementioned preparation process (a), by a catalytic hydrogen reduction of the compounds represented by the aforementioned formula (IX) häving a nitro group in place of an amino group, corresponding to the amino group (R3 ='H) in the formula (UI).
The catalytic hydrogen reduction can be conducted in an adequate diluent and as examples of the diluent used in that case there can be mentioned ethers, for example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, tetrahydrofuran (THF); alcohols, for example, methanol, etha-nol, isopropanol, butanol, ethylene glycol, and as catalytic reduction catalyst there can be mentioned palladium carbon, Raney nickel, platinum oxide.
It can be conducted at the temperatures generally between about O to about 100°C, preferably room temperature to about 80°C.
Said reaction can be operated under normal pressure to elevated pressure.
For example, an objective compound of the formula (UI), in which R3 represents hydrogen, can be obtained by hydrogenation of l mole of the nitro compound in a diluent, for example, ethanol in the presence of 0.1-10 % (w/w) palladium carbon.
Moreover, the compounds of the formula (IH), in which R3 represents hydrogen, can also be obtained by a reaction with a metal ete. instead of a catalytic hydrogen reduction.
As a process using a metal ete. there can be mentioned, for example, a process of treating iron powder in acetic acid, a process of reacting zinc dust under the neutral condition (Organic Syntheses Collective Vol. E, p. 447), a process of reacting stannic chloride under an acidic condition (Organic

Syntheses Collective Vol. H, p. 254), a process of reacting titanium trichloride under the neutral condition, ete.
As specific examples of the compounds of the formula (III), in which R3 represents a hydrogen atom,
there can be mentioned, for example,
l-(4-amino-3-methyl-benzyl)-lH-pyrazole,
l-(4-amino-3-rnethyl-benzyl)-3-methyl-lH-pyrazole,
l-(4-amino-3-methyl-benzyl)-4-methyl-lH-pyrazole,
l-(4-amino-3-niethyl-benzyl)-4,5-dichloro-lH-imidazole,
l-(4-amino-3-methyl-benzyl)-lH-l,253-triazole,
l -(4-amino-3-methyl-benzyl)- IH-1,2,4-triazole,
l-(4-amino-3-methyl-benzyl)-lH-tetrazole, .
l-(4-arnino-3-rnethyl-benz3'l)-5-methyl-lH-te1razoleJ
l-(4-amino-3-methyl-benzyl)-5-(2-chloro-phenyl)-lH-tetrazole,
l -(4-amino-3 -methyl-benzyl)-5 -(3-trifluoromethyl-phenyl)- IH-tetrazole,
% l-(4-amino-3-rnethyl-benzyl)-5-(4-trifluorornethyl-phenyl)-lH-tetrazole.,
l-(4-arm'no-3-]jiethyl-benzyl)-5-(3,5-bis-trifluoromethyl-phenyl)-lH-tetrazole,
l -(4-amino-3 -meth)d-benzyl)-5 -(3 -trifluoromethoxy-phenyl)-1 H-tetrazole,
l-(4-arrmo-3-methyl-benzyl)-3-(4-trifluoromethyl-phenyl)-imidazolydm-2-oneJ
l-(4-ammo-3-methyl-benzyl)-3-(4-1rifluorome1hyl-phenyl)-l,3-dihydro-
l -(4-amino-3 -methyl-benzyl)-3 -(4-trifluoromethyl-phenyl)-irtiidazolydin-2,4-dione,
!-(4-arrmo-3-me1hyl-benzyl)-3-(4-1iifluorometia}d-phen34)-imidazolydm-2,4J5-1rione.,
l-(4-amino-3-rnethyl-benzyl)-3-(4-trifluoromethyl-phenyl)-lH-pyrazole,
4-(4-amino-3 -methyl-benzyl)-2-(2-fluoro-phenyl)-2.,4-dihydro-1,2,4-triazol-3 -one,
4-(4-amino-3-methyl-benzyl)-2-(2-chloro-phenyl)-2,4-dihydro-l,2J4-triazol-3-oneJ
4-(4-amino-3-niethyl-benzyl)-2-(2-1rifluoromethyl-phenyl)-234-dihydro-l,2,4-triazol-3-one,
4-(4-arniiio-3-methyl-benzyl)-2-(3-fluoro-phenyl)-2,4-dihydro-l,2,4-triazol-3-one,
4-(4-amino-3-methyl-benzyl)-2-(3-chloro-phenyl)-2,4-diliydro-l,2J4-triazol-3-one,-
4-(4-amino-3-memyl-beri2yl)-2-(3-trifluorometliyl-phenyl)-2,4-düiydro-l,2,4-tiiazol-3-oneJ
2-(4-fluoro-phenyl)-4-(4-amino-3-methyl-benzyl)-2,4-dihydro-l,2,4-triazol-3-one,
4-(4-anTino-3-rnethyl-benzyl)-2-(4-chloro-phenyl)-2,4-dihydro-l,2.,4-triazol-3-one,
4-(4-anoino-3-methyl-benzyl)-2-(4-1rifiuoromethyl-phenyl)-234-dihydro-l,2,4-triazol-3-one,
4-(4-amino-3 -methyl-benzyl)-2-(3,4-bis-trifluoromethyl-phenyl)-234-dihydro-1,234-triazol-3 -one,
4-(4-ammo-3-methyl-beri2yl)-2-(335-bis-trifluoromethyl-phenyl)-2,4-dmydro-l,2J4-1iiazol-3-on
4-(4-amrno-3-methyl-benzyl)-5-1rifluorome
triazol-3-one.,
2-(4-ammo-3-rnethyl-benzyl)-4-(2-chloro-phenyl)-2J4-dihydro-l,2,4-triazol-3-oiie3

2-(4-aiimo-3-methyl-benzyl-4-
2-(4-amino-3-me1hyl4)enzyl)-5-methyl-4-(4-tr
2-(4-amino-3 -methyl-benzyl)-4-(2-chloro-phenyl)-5 -methylsulfanyl-234-dihydro-132,4-triazol-3-one3
2-(4-amino-3-methyl-benzyl-5-methylsulfanyl-4
triazol-3-one,
l-(4-amino-3-methyl-beri2yl)-4-methyl-lJ4-dihydro-tetrazol-5-oneJ
l -(4-amino-3-methyl-benzyl)-4-ethyl-1,4-dihydro-tetrazol-S-one,
l -(4-amino-3-methyl-benzyl)-4-propyl-1,4-dihydro-tetrazol-5-one,
l -(4-amino-3-methyl-benzyl)-4-isobutyl-1,4-dihydro-tetrazol-5 -one,
l -(4-amino-3-methyl-benzyl)-4-(2,2,2-trifluoro-ethyl)-134-dihydro-tetrazol-5-one3
l-(4-amino-3-methyl-benz3'l)-4-(4J4,4-trifluoro-butyl)-lJ4-diliydro-tetrazol-5-one,
l-(4-amino-3-methyl-benzyl)-4-(3,3,3-trich]oro-2-methyl-propyl)-l)4-dihydro-tetrazol-5-one,
l -(4-amino-3-methyl-benzyl)-4-cyclopropyl-1,4-dihydro-tetrazol-S-one.,"
l -(4-amino-3-methyl-benzyl)-4-cyclohexyl-1,4-dihydro-tetrazol-5-one,
l -(4-amino-3-methyl-benzyl)-4-phenyl-1,4-dihydro-tetrazoI-5-one,,
l-(4-amino-3-methyl-benzyl)-4-(2-fluoro-phenyl)-l,4-dihydro-tetrazol-5-onea
l -(4-amino-benzyl)-4-(2-cMoro-phenyl)-1,4-dihydro-tetrazol-5-one.,
l -(4-aminp-3-methyl-benzyl)-4-(2-chloro-phenyl)-1-dihydro-tetrazol-S-one,
l-[l-(4-ariiino-3-methyl-phenyl)-ethyl]-4-(2-cliloro-phenyl)-lJ4-dihydro-tetrazol-5-one3
l-(4-anaino-3-methyl-benzyl)-4-(2-methyl-phenyl)-l,4-dihydro-tetrazol-5-one.,
l-(4-amino-3-methyl-berizyl)-4-(2-methoxy-phenyl)-l34-dihydro-tetrazol-5-one3
l -(4-amino-3-methyl-benzyl)-4-(2-trifluorome1;hyl-phenyl)-1,4-dihydro-tetrazol-5-one.,
l-(4-amino-3-methyl-benzyl)-4-(2-1rifluoromethoxy-phenyl)-l34-diliydro-tetrazol-5- one,
l-(4-amino-3-metliyI-benzyl)-4-(3-fluoro-phenyl)-l34-diliydro-tetrazol-5-one3
l-(4-amino-3-methyl-benzyl)-4-(3-chloro-phenyl)-l34-dihydro-tetrazol-5-one,
l-(4-amino-3-meth3d-benzyl)-4-(3-methyl-phenyl)-l34-dihydro-tetrazol-5-one3
l-(4-aniino-benzyl)-4-(3-trifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one3
l-(4-amino-3-methyl-benzyl)-4-(3-trifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one3
l-(4-amino-3-methyl-benzyl)-4-(3-difluoromethoxy-phenyl)-l34-dihydro-tetrazol-5-one3
l -(4-amino-3 -methyl-benzyl)-4-(3 -trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5- one,
l-(4-amino-3-methyl-benzyl)-4-(4-fiuoro-phenyl)-l34-dihydro-tetrazol-5-one3
l-(4-aniino-3-methyl-benzyl)-4-(4-cMoro-phenyl)-l,4-dihydro-tetrazol-5-one,
l-(4-amino-3-methyl-benzyl)-4-(4-bromo-phenyl)-l34-dihydro-tetrazol-5-one3
l -(4-amino-3 -methyl-benzyl)-4-(4-methyl-phenyl)-1,4-dihy dro-tetrazol-5-one,
l -(4-amino-3-methyl-benzyl)-4-(4-isopropyl-phenyl)-1,4-dihydro-tetrazoI-5-one3
l -(4-amino-benzyl)-4-(4-trifluoromethyl-phenyl)-134-dih.ydro-tetrazol-5-one3
l -(4-amino-2-chloro-benzyl)-4-(4-trifluoromethyl-phenyl)-134-dihydro-tetrazol-5-one3

l -(4-amino-3-chloro-benzyl)-4-(4-trifl'uorornethyl-phenyl)-1,4-dihydro-tetrazol-5-one,
l -(4-amino-3-methyl-berizyl)-4-(4-trifluoromethyl-phenyl)-1 ,4-dihydro-tetrazol-5-one.,
l-(4-amino-3-methyl-benzy1)-4-(4-difluoromethoxy-phenyl)-l,4-dihydro-tetrazol-5-oneJ
l-(4-amino-3-methyl-benzyl)-4-(4-trifluoromethoxy-phenyl)-lJ4-dihydro-tetrazol-5- one,
l -(4-amino-3-methyl-benzyl)-4-(4-trifLuoromethylsulfanyl-phenyl)-1 34-dihydro-tetrazol-5-one3
l -(4-amino-3-methyl-benzyl)-4-(4' -trifluoromethyl-biphenyl-4-yl)-134-dihydro-tetrazol-5-one,
l -(4-aminq-3-methyl-benzyl)-4-(3' ,5 '-bis-trifluoromethyl-biphenyl-4-yl)-1,4-dihydro-tetrazol-5-one,
l -(4-amino-3-methyl-benzyl)-4-(4-bromo-2-fluoro-phenyl)-1 ,4-dihydro-tetrazol-5-one3
l -(4-amino-3-methyl-benzyl)-4-(2-fluoro-3 -trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one;
l-(4-amino-3-methyl-benzyl)-4-(3-bromo-4-trifluoromethoxy-phenyl)-l,4-dihydro-tetrazol-5-one3
l-(4-amino-3-methyl-benzyl) -(3-cUoro-4-trifluorome1hoxy-phenyl)-l,4-dihydro-tetrazol-5-on
l-(4-amino-3-methyl-benzyl) -(4-fluoro-3-trifluoromethyl-phenyl)-lJ4-dih.ydro-tetrazol-5-one5
l-(4-amino-3-methyl-benzyl)-4-(2-fluoro-5-trifluoromethyl-phenyl)-l)4-dihydro-tetrazol-5-one3
l-(4-amino-3-methyl-benzyl)-4-(4-chloro-3-1rifluoromethyl-phenyl)-l,4-dihydro-tetrazol-5-one)
l-(4-aniino-3-methyl-beaxzyl)-4-(3,4-dichloro-phenyl)-l,4-diliydro-tetrazol-5-one3
l-(4-amino-3-methyl-benzyl)-4-(3,4-bis-l-(4-amino-3-methyl-benzyl)-4-(3-fluoro-5-trifluoromethyl-phenyl)-l,4-dihydro-te1razol-5-one3
l -(4-amino-3 -methyl-benzyl)-4-(3 35-dichlorõ-phenyl)-134-dihydro-tetrazol-5 -one,
l-(4-amino-3-methyl-benzyl)-4-(335-diriiethoxy-pb.enyl)-l34-dihydro-tetrazol-5-one3
l-(4-amino-2-cUoro-benzyl)-4-(3,5-bis-trifluoromethyl-phenyl)-l.,4-dihydro-tetrazol-5-one3
l-(4-amino-3-cKloro-benzyl)-4-(335-bis-1iifluoromethyl-phenyl)-l34-dihydro-tetrazol-5-one3
l -(4-amino-3 -methyl-benzyl)-4-(3,5-bis-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,
!-(4-animo-2-me1hoxy-benzyl)-4-(3,5-bis-trifluoromethyl-phenyl)-l34-dih)'dro-tetrazol-5-one3
l -(4-amino-3-methoxy-benz)4)-4-(3,5-bis-trifluoromethyl-phenyl)-1 -dihydro-tetrazol-S-one,
l -(4-amino-3,5-dimethyI-benzyl)-4-(3,5-bis-triiluoromethyl-phenyl)-1 -dihydro-tetrazol-S-one,
l -[ l -(4-amino-3-methyl-phenyl)-ethyl]-4-(3,5-bis-trifluoromethyl-phenyl)-1 -dihydro-tetrazol-S-one,
l-(4-amino-3-me&yl-benzyl)-4-(3-cbJoro-2-me.thoxy-5-niethyl-phenyl)-lJ4-dihydro-tetrazol-5-one5
l-(4-amino-3-methyl-bejQzyl)-4-(2,2-difluoro-benzo[lJ3]dioxol-5-yl)-l,4-dihydro-tetrazol-5-one,
l -(4-amino-3-methyl-benzyl)-4-(2,2,3?3-tetrafluoro-2,3-dihydro-benzo[l ,4]dioxin-6-yl)-1,4-dihydro-
tetrazol-5-one,
l-(4-ainino-3-methyl-benzyl)-4-(2,2J3-1rifluoro-2)3-dihydro-benzo[l,4]dioxin-6-yl)-l)4-dihydro-
tetrazol-5-one,
l -(4-amino-3-naethyl-benzyl)-4-(2,3,3-trifluoro-2)3-dihydro-benzo[l ,4]dioxin-6-yl)-1,4-dihydro-
tetrazol-5-one,
l-(4-amino-3-methyl-benzyl)-4-(232]3,3,7-pentafluoro-233-diliydro-benzo[l34]dioxin-6-yl)-l34-
dihydro-tetrazol-5-one,
l -(4-amino-3 -methyl-benzyl)-4-(3,5 -dichloro-2,6-diethyl-phenyl)-1,4-dib.ydro-tetrazol-5-one,

1 -(4-amino-3 -methyl-benzyl)-4-benzyl- 1 ,4-dihydro-tetrazol-5-one,
l -(4-amino-3 -mefhyl-benzyl)-4-(4-fluoro-benzyl)- 1 ,4-dihydro-tetrazol-5-one,
l -(4-amino-3-methyl-benzyl)-4-(4-chloro-phenyl)- 1 ,4-dihydro-tetrazol-5-one,
l-(4-amino-3-methyl-benzyl)-4-(4-trifluoromethyl-phenyl)-l,4-dihydro-tetrazol-5-one,
l-(4-amino-3-methyl-benzyl)-4-[l-(2-fluoro-phenyl)efhyl]-l)4-dihydro-tetrazol-5-one)
l -(4-amino-3-methyl-benzyl)-4-[l -(2-chloro-phenyl)-ethyl]- 1 ,4-dihydro-tetrazol-5-one,
l-(4-amino-3-methyl-benzyl-[l-(2-trifluoromethyl-phenyl)-ethyl]-l,4-dihydro-tetrazol-5-one)
l-(4-amino-3-methyl-benzyl)-4--l-[l-(3-fluoro-phenyl)-ethyl]-l)4-dihydro-tet:azol-5-oneJ
l-(4-amino-3-methyl-benzyl)-4-[l-(3-cbloro-phenyl)-ethyl]-l.,4-diliydrõ-tetrazol-5-one,
l-(4-arnmo-3-memyl-benzyl)-4-[l-(3-trifl
l-(4-ainirLO-3-methyl-berizyl)-4-[l-(4-£Iuoro-pheny])-e1iiyl]-l,4-dihydro-tetrazol-5-oneJ
l -(4-amino-3-methyl-benzyl)-4- [ l -(4-chloro-phenyl)-ethylj- 1 ,4-dihy dro-tetrazol-5-one,
l -(4-amino-3-methyl-benzyl)-4-[ l -(4-trifluoromethyl-phenyl)-ethyl]-l ,4-dihydro-tetrazol-5-one,
l -(4-ammo-3-methyl-benzyl)-4-[ l -(2,4-difluoro-phenyl)-ethyl]- 1 ,4-dihydro-tetrazol-5-one,
l-(4-amino-3-methyl-benzyl)-4-[l-(2)4-dichloro-phenyl)-ethyl]-l,4-dihydro-tetrazol-5-one,
l-(4-aminb-3-methyl-benzyl)-4-[l-(3;4-difluoro-phenyl)--ethyl]-l.,4-dih3'dro-tetrazol-5-one.
The compounds of the above-mentioned formula (IX) are novel compoxinds and can be obtained, for example, by reacting compounds of the formula
(Figure Removed)wherein Y, m, A1 and r have me same defmition as aforementioned and M represents chloro, bromo or methylsulfonyloxy, and compounds of the formula
wherein Q, A2, s and E have tlae same definition as aforementioned.
The compounds of the above-mentioned formula (XI) are compounds well knov m in the field of organic chemistry (cf. Chem. Abstr. 1963, 55, 3444e; Bull Soe. Chim. Fr. 1934, 539-545; J. Chem. Res. Mmiprint, 1987, 8, 2133-2139; J. Chem. Soe. B 1967, 1154-1158; J, Chem. Soe. 1961, 221-222; J. Amer. Chem. Soe. 1989, 111, 5880-5886). Specifically there can be mentioned as examples 4-nitrobenzyl chloride, (available on the market) 4-bromobenzyl chloride, (available on the market) 2-chloro-4-mtrobenzyl chloride, 2-methyl-4-nitrobenzyl chloride,

2-memoxy-4-nitrobenzyl chloride, 3-chloro-4-nitrobenzyl chloride, 3-memyl-4~nitrobenzyl chloride, 3-methoxy-4-nitrobenzyl chloride, 4-nitrobenzyl methanesulfonate, 2-cUoro-4-mtrobeiizyl methanesulfonate, 2-methyl-4-nitrobenzyl methanesulfonate, 2-methoxy-4-nitrobenzyl methanesulfonate, 3-chloro'-4-nitrobenzyl methanesulfonate, 3 -methyl-4-nitrobenzyl methanesulfonate, 3-methoxy-4-nitrobenzyl methanesulfonate, l -(3-chloro-4-nitxo-phenyl)-ethyl methanesulfonate, l -(3-methyl-4-nitro-phenyl)-ethyl methanesulfonate, l-(3-methoxy-4-nitro-phenyl)-ethyl methanesulfonate.
The nitro-substituted benzoic acids and their esters, starting materials for the compounds of the formula (XI) are kno\vn from the literature (cf., for example, Chem. Ber. 1919, 52, 1083; Bull. Soe. Chim. Fr. 1962,2255-2261; Tetrahedron 1985, 115-118; Chem. Pharm. Bull, 1993, 41, 894-906).
The compounds of the above-mentioned formula (Xn) include known compounds and as their
specific examples there can be mentioned,
IH-pyrrole,
3 -methyl- IH-pyrrole,
2,5-dimethyl-lH-pyrrole,
IH-pyrazole,
3 -methyl-1 H-pyrazole,
4-methyl- IH-pyrazole,
4-chloro-lH-pyrazole,
3,5-dimethyl-lH-pyrazole,
IH-imidazole,
4-methyl- IH-imidazole,
4,5-dichlqro-lH-imidazole,
lH-[lA3]-triazole,
lH-[l,2,4]-triazole,
IH-tetrazole,
5-metyl-lH-tetrazole,
5 -phenyl- IH-tetrazole,

5-(2-chloro-plien)'l)- IH-tetrazole,
5-(4-chloro-phenyl)- IH-tetrazole,
5-(3-trifluoromethyl-phenyl)-lH-tetrazole3
5-(4-trifluoromethyl-phenyl)-lH-tetrazole,
5-(3,5-bis-trifluoromethyl-phenyl)- IH-tetrazole,
5-(3-trifluoromethoxy-phenyl)-lH-tetrazole,
succinimide.,
l-(4-trifluoromethyl-phenyl)-imidazolidin-2-one
l -(4-trifluoromethyl-phenyl)-1,3 -dihydro-imidazol-2-one,
3-(4-trifluoromethyl-phenyl)-imidazolidin-2,4-dione
2-(2-chloro-phenyl)-2,4-dihydro-[l32,4]triazol-3-ohe,
2-(2-trifluoromethyl-phenyl)-2,4-dihydro-[ l ,2,4]triazol-3-one,
2-(3-fluoro-pheayl)-2,4-dihydro-[l,2,4]tri-azol-3-one,
2-(3-chloro-phenyl)-2,4-dihydro-[l,2,4]triazol-3-one,
2-(3-trifluoromethyl-phenyl)-2,4-dihydro-[l,2J4]triazol-3-one,
'v*
2-(4-fluoro-phenyl)-2,4-dihydro-[l,2,4]triazol-3-one,
2-(4-chloro-phenyl)-2)4-dih}'dro-[l)2,4]triazol-3-one,
2-(4-trifluoromethyl-phenyl)-254-dihydro-[l,2,4]triazol-3-oiie3
2-(3,4-bis-trifIuoromeäiyl-phenyl)-2.,4-dihydro-[l,234]triazol-3-one,
2-(3,5-bis-trifluoromethyl-phenyl)-2,4-dihydro-[ l ,234]triazol-3-one,
5-trifluoromethyl-2-(4-trifluorometh.yl-phenyl)-234-dihydro-[l3234]triazol-3-one,
4-(2-chIoro-phenyl)-2,4-dihydro-[l3234]triazol-3-one3
4-(4-trifluoromethyl-phenyl)-234-dih.ydro-[ l ,234]triazol-3 -one,
5-methyl-4-(4-trifluoromethyl-phenyl)-234-düiydro- [ l ,234Jtriazol-3 -one,
4-(2-chloro-phenyl)-5-methylsulfanyl-2,4-dihydro-[l3234]triazol-3-one,
5-meth}'lsulfanyl-4-(4-trifluoromethyl-phenyl)-2)4-dihydro-[l32,4]triazol-3-one3
l -methyl-134-dihydi-o-tetrazol-5-one3
l -ethyl-1,4-dihydro-tetrazol-S-one,
l-propyl-l,4-dihydro-tetrazol-5-one,
l-isobutyl-l34-dihydro-tetrazol-5-one,
l -(2,2,2-trifluoro-eÜiyl)-134-dihydro-tetrazol-5-oiae;
l -(4,4,4-trifluoro-butyl)-1 dihydro-tetrazol-S-one,
l-(3,3,3-trichloro-2-methyl-propyl)-134-dihydro-tetrazol-5-one3
l -cyclopropyl-1,4-düiydro-tetrazol-5-one,
l-cyclohexyl-l34-dihydro-tetrazol-5-one3
l-phenyl-l34-dihydro-tetrazol-5-one3
l-(2-fluoro-phenyl)-l34-dihydro-tetrazol-5-one3

1 -(2-chloro-phenyl)-l ,4-dihydro-tetrazol-5-one,
l -(2-methyl-phenyl)-1,4-dihydro-tetrazol-5 -one,
l -(2-methoxy-phenyl)-1 ,4-dihydro-tetrazol-5-one,
l-(2-trifluoromethyl-phenyl)-l,4-dihy(iro-tetrazol-5-one,
l-(2-trifluoromethoxy-phenyl)-lJ4-dihydro-tetrazol-5-one, .
l -(3 -fluoro-phenyl)-1,4-dihydro-tetrazol-5 -one,
l -(3 -cliloro-phenyl)-1,4-dihydro-tetrazol-5-one,
l-(3 -methyl-phenyl)-1,4-dihydro-tetrazol-5 -one,
l -(3 -trifluoromethyl-phenyl)-1.,4-dihy dro-tetrazol-5 -one,
l-(3-difluorometiioxy-phenyl)-l54-dihydro-tetrazol-5-one,
l -(3 -trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,
l -(4-fluoro-phenyl)-1,4-dihydro-tetrazol-5 -one,
l-(4-chloro-phenyl)-l,4-dihydro-tetrazol-5-one,
l-(4-bromo-phenyl)-l,4~dihydro-tetrazol-5-one,
l-(4-methyl-phenyl)-l,4-diliydro-tetra2ol-5-one,
l-(4-isopropyl-phenyl)-l,4-düiydro-tetrazol-5-one,
l -(4-trifluorometii)'l-phenyl)-1,4-diliydro-tetrazol-5 -one,
l-(4-difluorometho7cy-phenyl)-l,4-dihydro-tetrazol-5-one3
l-(4-trifluoromethoxy-phenyl)-l,4-dihydro-tetrazol-5-one,
l -(4-trifluorometiaylsulfanyl-phenyl)-1,4-dihy dro-tetrazol-5 -one,
l -(4' -trifluoromethyl-biphenyl-4-yl)-1,4-dihydro-tetrazol-5-one,
l -(3' ,5' -bis-trifluoromethyl-biphenyl-4-yl)-1,4-dihydro-tetra2ol-5-one,
l -(4-bromo-2-iluoro-phenyl)-1,4-düiydro-tetrazol-5-one,
l -(2-fluoro-3 -trifluorometh}'l-phenyl)-1,4-dih.ydro-tetrazol-5-one,
l-(3-bromo-4-trifluoromethoxy-phenyl)-l,4-dihydro-tetrazol-5-one,
l-(3-chloro-4-trifluoromet:hoxy-phenyl)-l,4-dihydro-te1razol-5-one,
l -(4-fluoro-3-trifluoromefhyl-phenyl)-1,4-dihydro-tetrazol-5-one,
l-(2-fiuoro-5-trifluoroniethyl-phenyl)-l,4-dihydro-tetrazol-5-one,
l -(4-chloro-3 -trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,
l -(3 54-dichloro-phenyl)-1,4-dihydro-tetrazol-5-one,
l -(3,4-dichloro-phenyl)-1,4-dihydro-tetrazol-5-one,
l-(3,4-bis-trifluoromethyl-phenyl)-l,4-dih.ydro-tetrazol-5-one,
l-(3-fluoro-5-trifluoromethyl-phenyl)-l,4-dihydro-tetrazol-5-one,
l-(3,5-dicrjloro-phenyl)-l54-dihydro-tetrazol-5-one)
(SjS-dimethoxy-pheny -l -dihydro-tetrazol-S-one,
l-(3,5-bis-trifluoromethyl-phenyl)-l,4-dihydro-tetrazol-5-one5
l -(3 -chloro-2-methoxy-5 -methyl-phenyl)-1,4-dihydro-tetrazol-5-one,

l-(2,2-difluoro-benzo[l,3]dioxol-5-yl)-l,4-dihydro-tetrazol-5-one,
l -(2,2,3,3-tetrafluoro-2,3 -dihydro-benzo[ l ,4] dioxin-6-yl)-1,4-düiy dro-tetrazol-5-one,
l-(2,2,3-trifluoro-233-dihydro-benzo[l,4]dioxin-6-yl)-l,4-dihydro-tetrazol-5-one,
l -(2,3,3 -trifluoro-2,3 -dihydro-benzo[ l ,4] dioxin-6-yl)-1,4-dürydro-tetrazol-5 -one,
l-(232,3,3}7-pentafluoro-2,3-dihydro-benzo[l,4]dioxin-6-yl)-l34-dihydro-tetrazol-5-one,
l-(3,5-dichloro-2,6-diethyl-phenyl)-l,4-dihydro-tetrazol-5-one,
l -thiophen-2-yl-1,4-dihydro-tetrazol-5 -one,
l -benzyl-134-dürydro-tetrazol-5-one,
l-(4-fluoro-benzyl)-1,4-dihydro-tetrazol-5-one,
l-(4-chloro-benzyl)-l,4-dihydro-tetrazol-5-one,
l -(4-trifluoromethyl-benzyl)-1,4-dihydro-tetrazol-5 -one,
l -[ l -(2-fluoro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,
l - [ l -(2-chloro-phenyl)-ethyl] -1,4-dihydro-tetrazol-5-one,
l -[ l -(2-trifluoromethyl-phenyl)-ethyl]-1,4-dihydro-tetrazol-5 -one,
l -[ l -(3-fluoro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,
l -[ l -(3-chloro-phenyl)-ethyl]-1,4-dihy dro-tetrazol-5-one,
l -[l -(3-trifluoromethyl-phenyl)-ethyI]-134-dihydro-tetrazol-5-one,
l -[ l -(4-fluoro-phenyl)-ethyl] -1,4-dihydro-tetrazol-5-one,
l -[ l -(4-chloro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,
l-[l-(4-trifluoromethyl-phenyl)-ethyl]-l,4-dihydro-tetrazol-5-one,
l -[ l -(2,4-difluoro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,
l-[l-(234-dichloro-phenyl)-eth}fl]-l34-dihydro-tetrazol-5-one,
l-[ l -(334-difluoro-phen}'l)-ethyl]-134-dihydro-tetrazol-5-one.
Furthermore, there can be provided from the processes described in the literature, for example, l-(4-trifluoromethylphenyl)imidazolidin-2,4,5-trione from 4-trifluoromethylphenylurea (cf. J. Cliem. Soe. Perkin Trans. 2, 1977, 934, according to the process described in Chem. Ber. 1907, 40, 3737), there can be provided 3-(4-trifluorornethylphenyl)-lH-pyrazole from 4-trifluoromethylacetophenone, available on the market (cf. Synthesis 2001, 55-62), and further there can be provided 2-phenyl-2,4-dihydro-l,2,4-triazol-3-one and 2-(2-fluorophenyl)-234-dihydro-l32,4-triazol-3-one (cf. J. Prakt. Chem. 1907, 75, 131), and furthermore, there can be provided l-mono-(or di-)(trüluoromethyl)-phenyl-l34-dihydro-tetrazol-5-one by a reaction of mono-(or di-)(trifluoromethyl)phenyl isocyanate and known trimethylsüyl azide (cf. EP-A O 146 279, Chem. Plwrm. Bull, 1996,44, 314-327).
The process to prepare the compounds of the above-mentioned formula (DQ can be conducted in an adequate diluent. As examples of the diluent used in that case there can be mentioned aliphatic, alicyclic and aromatic hydrocarbons (may be optionally chlorinated), for example, pentane, hexane,

cyclohexane, petroleum ether, ligroine, benzene, toluene, xylene, dichloromethane; ethers, for example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF), dieüiylene glycol dimethyl ether (DGM); ketones, for example, acetone, methyl ethyl ketone (MEK), methyl isopropyl ketone, methyl isobutyl ketone (MEBK); niüiles, for example., acetonitrile, propionitrile, acrylonitrile; esters, for example, ethyl acetate, amyl acetate; acid amides, for example, dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone, l,3-dimethyl-2-imidazolidinone, hexamethyl phosphoric triamide (HMPA).
The reaction can be conducted in the presence of an acid binder and as such an acid binder there can be mentioned, as inorganic base, hydrides, hydroxides, carbonates, bicarbonates, ete. of alkali metals and alkaline earth metals, for example, sodium hydride, lithium hydride, sodium hydrogen carbonate, potassiuni hydrogen carbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide; inorganic alkali metal amides, for example, lithium amide, sodium amide, potassium amide; as organic base, alcoholates, tertiary amines,
dialkylaminoanilines and pyridines., for example, triethylamine, 1,1,4,4-tetramethylethylenediamine
(TMEDA), N,N-dimethylaniline, N,N-diethylaniline, pyridine, 4-dimethylaminopyridine (DMAP), l34-diazabicyclo[2.2.2]octane (DABCO) and l,S-diazabicyclo[5.4.0]undec-7-ene (DBU).
The reaction can also be conducted by a process using a phase-transfer catalyst. As examples of the diluent used in that case there can be mentioned water; aliphatic, alicyclic and aromatic hydrocarbons (may be optionally chlorinated), for example, pentane, hexane, cyclohexane, petroleum ether, ligroine, bensene, toluene, xylene; ethers, for example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF), diethylene glycol dimethyl ether (DGM).
As examples of phase-transfer catalyst there can be mentioned, quaternary ions, for example, tetra-merhylammonium bromide, tetrapropylammonium brornide, tetrabutylammonium bromide, tetrabu-tylammonium bissulfate, tetrabutylammonium iodide, trioctylmethylammonium chloride, benzyl-triethylammoniuni bromide, butylpyridinium bromide, heptylpyridinium bromide, benzyltri-etiiylammonium chloride; crown ethers, for example, dibenzo-18-crown-6, dicyclohexyl-lS-crown-6, 18-crown-6; cryptands, for example, [2.2.2]-cryptate, [2.1.1]-cryptate, [2.2.1]-cryptate, [2.2.B]-cryptate, [202O2S]-cryptate, [3.2.2]-cryptate.
The reaction can be conducted in a substantially wide range of temperature. It can be conducted at the temperatures in a range of generally about 0°C to about 200°C, preferably room temperature to about 150°C. Although said reaction is conducted desirably under normal pressure, it can be operated also under elevated pressure or under reduced pressure.

In conducting Üie reaction, the aimed compounds can be obtained, for example, by reacting l mole amount to a little excess amount of a compound of the formula QÖI) to l mole of the compounds of the formula (XT) in a diluent, for example, DMF, in the presence ofpotassium carbonate.
As specific examples of the compounds of the aforementioned formula (IX), obtained according to
the above-mentioned process, there can be mentioned, for example, l-(4-nitro-benzyl)- IH-pyrrole, l-(3-memyl-4-nitro-benzyl)-lH-pyrazole,
3-methyl-l-(3-meth}'l-4-nitro-benzyl)-lH-pyrazole,
4-methyl-1 -(3-methyl-4-nitro-benzyl)- IH-pyrazole,
4,5 -dichloro-1 -(3 -methyl-4-nitro-benzyl)- IH-imidazole,
l-(3-methyl-4-nitro-benzyl)-lH-l ,2,3-triazole,
l-(3-methyl-4-nitro-benzyl)-lH-l,2,4-triazole,
l -(3 -methyl-4-nitro-benzyl)-1 H-tetrazole,
5-methyl-1 -(3 -methyl-4-nitro-benzyl)- IH-tetrazole,
5-(2-chloro-phenyl)-l-(3-methyl-4-nitro-benzyl)-lH-tetrazole,
5-(3-trifluoromethyl-phenyl)-l-(3-methyl-4-nitro-benzyl)-lH-tetrazole,
5-(4-1rifluorometfryl-phenyl)-1 -(3-methyl-4-nitro-benzyl)- IH-tetrazole,
5-(3,5-bis-trifluoromethyl-phenyl)-l-(3-meÜa}d-4-nitro-benzyl)-lH-tetrazole;
5-(3-trifluoromethoxy-phenyl)-l-(3-rnethyl-4-nitro-benzyl)-lH-tetrazole,
l-(3-methyl-4-mtro-berjzyl)-3-(4-trifluoromethyl-phenyl)-irnidazolidin-2-one5
l -(3 -methyl-4-iütro-benzyl)-3 -(4-trifluorometüyl-phenyl)-1,3-dihydro-imidazol-2-one,
l -(3 -methyl-4-nitro-benzyl)-3 -(4-triflu.oromethyl-phenyl)-imidazolidin-2,4-dione,
l-(3-mefhyl-4-nitro-benzyl)-3-(4-1rifluoromemyl-phenyl)-irrddazolidin-2,4,5-trione,
l-(3-niethyl-4-nitro-benzyl)-3-(4-trifluoromethyl-phenyl)-lH-pyrazole,
2-(2-fluoro-phenyl)-4-(3-methyl-4-nitro-benz3'l)-2,4-dihydro-l,2,4-triazol-3-one,
2-(2-chloro-phenyl)-4-(3-methyl-4-nitro-benzyl)-2,4-dihydro-l,2,4-triazol-3-one,
4-(3-methyl-4-nitro-benzyl)-2-(2-tiifluoromethyl-phenyl)-2)4-dihydro-l,2;4-triazol-3-one)
2-(3 -fluoro-phenyl)-4-(3 -meth}'l-4-nitro-benzyl)-2,4-dihy dro-1,2,4-triazol-3 -one,
2-(3-chloro-phenyl)-4-(3-methyl-4-nitro-benzyl)-2,4-dihydro-l,2,4-triazol-3-one,
4-(3-methyl-4-nitro-benzyl)-2-(3-trifluorometl-iyl-phenyl)-2,4-düaydro-l,2,4-triazol-3-one,
2-(4-fluoro-phenyl)-4-(3-metliyl-4-nitro-benzyl)-2,4-dihydro-l,2,4-triazol-3-one,
2-(4-chloro-phenyl)-4-(3 -methyl-4-nitro-benzyl)-2,4-dihydro-1,2,4-triazol-3 -one,
4-(3-memyW-nitro-benzyl)-2-(4-trifluoromethyl-phenyl)-2,4-dihydro-l,2,4-triazol-3-one,
2-(3,4-bis-trifluoromethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-2,4-dihydro-l,2,4-triazol-3-one,
2-(3,5-bis-trifluoromethyl-phenyl)-4-(3 -methyl-4-nitro-benz3'l)-2,4-dihydro-1,2,4-triazol-3 -one,
4-(3-meftyl-4-nitro-benzyl)-5-1rifiuoromethy

3-one,
4-(2-cUoro-phenyl)-2-(3-methyl-4-ni1ro-benzyl)-234-dihydro-l,2,4-tiiazol-3-one3
2-(3-methyl-4-ni1io-benzyl)-4-(4-1iifluoromethyl-phenyl)-2,4-dihydro-l,2,4-triazol-3-oneJ
5-methyl-2-(3-methyl-4-iiitro-benzyl)-4-(4-ti
4-(2-cMoro-phenyl)-2-(3-methyl-4-mtrö-benzyl)-5-methylsulfäml-2)4-dihydro-l,234
2-(3-methyl-4-nitro-beoo2yl)-5-methylsulf
3-one,
l-meftyl-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,
l-ethyl-4-(3-methyl-4-nitro-benzyl)-l)4-dihydro-tetrazol-5-one,
l -propyl-4-(3 -methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5 -one,
l -isobutyl-4-(3 -methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-S-one,
l -(3-methyl-4-nitro-benzyl)-4-(2J2,2-trifluoro-ethyl)-1,4-dihydro~tetrazol-5-one,
l-(3-methyl-4-nitro-benzyl)-4-(41434-trifluoro-butyl)-l34-dibydro-tetrazol-5-oneJ
l-(3-methyl-4-ni1xo-benzyl)-4-(333,3-trichloro-2-mefhyl-propyl)-l,4-dihydro-tetrazol-5-one.,
l -cycldpropyl-4-(3-methyl-4-nitro-benzyl)-134-dihydro-tetrazol-5-one,
l-cyclohexyl -fS-methyM-nitro-benzyl-l-dihydro-tetrazol-S-one.,
l-(3-methyl-4-nitro-benzyl)-4-phenyl-l34-dihydro-tetrazol-5-one,
l-(2-fluoro-phenyl)-4-(3-methyl-4-nitro-benzyl)-l,4-dih.ydro-tetrazol-5-one3
l-(2-chloro-phenyl)-4-(4-nitro-benzyl)-l,4-dih.ydro-tetrazol-5-one3
l-(2-chloro-phenyl)-4-(3-methyl-4-mtro-benzyl)-l,4-dihydro-tetrazol-5-one3
l-(2-chloro-phenyl)-4-[l-(3-methyl-4-nitro-phenyl)-ethyl]-lJ4-dihydro-tetrazol-5-one,
l -(3-methyl-4-nitro-benzyl)-4-(2-methyl-phenyl)-1,4-dihydro-tetrazol-5 -one,
l-(3-methyl-4-nitro-benzyl)-4-(2-methoxy-phenyl)-l34-dihydro-tetrazol-5-one,
l-(3-methyl-4-nitro-benzyl)-4-(2-trifluoromethyl-phenyl)-l,4-dihydro-tetrazol-5-one3
l-(3-methyl-4-nitro-benzyl)-4-(2-trifluoromethoxy-phenyl)-l,4-dihydro-tetrazol-5-one,
l-(3-fluoro-phenyl)-4-(3-methyl-4-nitro-benzyl)-l,4-dihydro-tetrazol-5-one3
l-(3-chloro-phen.yl)-4-(3-methyl-4-riitro-benzyl)-l34-dih.ydro-tetrazol-5-one3
l-(3-methyl-4-nitro-benzyl)-4-(3-methyl-phenyl)-l34-dihydro-tetrazol-5-one3
l-(4-nitro-benzyl)-4-(3-trifluoromethyl-phenyl)-l34-dihydro-tetra2ol-5-one;
l-(3-methyl-4-nitro-benzyl)-4-(3-trifluoromethyl-phenyl)-l ,4-dihydro-tetrazol-S-one, .
l-(3-difluoromethoxy-phenyl)-4-(3-met;hyl-4-nitro-benzyl)-l,4-dihydro-tetrazol-5-one3
l-(3-methyl-4-nitro-benzyl)-4-(3-trifluoromethoxy-pb.enyl)-l34-diliydro-tetrazol-5-one3
l-(4-fluoro-phenyl)-4-(3-methyl-4-nitro-benzyl)-l34-dihydro-tetrazol-5-one,
l-(4-chloro-phenyl)-4-(3-methyl-4-nitro-benzyl)-l34-dihydro-tetrazol-5-one3
l-(4-bromo-phenyl)-4-(3 -methyl-4-nitro-benzyl)-134-dib.ydro-tetrazol-5-one3
l-(3-methyl-4-nitro-benzyl)-4-(4-methyl-phenyl)-l34-düiydro-tetrazol-5-one,
l-(4-isopropyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-l34-dLhydro-tetrazol-5-one3

l-(4-nitro-benzyl)-4-(4-trifluoromethyl-phenyl)-l.,4-dihydro-tetrazol-5-one3
l -(2-cMoro-4-nitro-benzyl)-4-(4-trifluoromethyl-phenyl)- 1 34-dihydro-tetrazol-5-one,
l-(3-cliloro-4-m1ro-benzyl)-4-(4-trifluoromethyl-phenyl)-l,4-düiydro-tetrazol-5-one)
l-(3-methyl-4-nitro-benzyl)-4-(4-trifliioroinefhyl-phenyl)-l,4-dihydro-tetrazol-5-oneJ
l -(4-difluoromethoxy-phenyl)-4-(3-methyl-4-nitro-benzyl)- 1 ,4-düiydro-tetrazol-5-one,
l-(3-mettiyl-4-nitro-berizyl)-4-(4-trifluoromethoxy-phenyl)-l)4-düiydro-tetrazol-5-oneJ
!-(3-methyl-4-nitro-benzyl)-4-(4-trifluoromethylsulfanü-phenyl)-l,4-düiydro-tetrazol-5-oneJ
!-(3-me1hyl-4-ni1io-benzyl)-4-(4'-trifluoromethyl-biphenyl-4-yl)-l)4-dihydro-tetrazol-5-one)
l -(3 ' ,5 ' -bis-trifluoromethyl-biphenyl-4-yl)-4-(3 -meÜ-iyl-4-nitro-benzyl)- 1 ,4-dihydro-tetrazol-5-one,
l -(4-bromo-2-fluoro-phenyl)-4-(3 -methyl-4-nitro-benzyl)- 1 ,4-dihydro-tetrazol-5-one,
l -(2-fluoro-3 -trifluoromethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)- 1 54-dihydro-tetrazol-5-one,
-%
l -(3-bromo-4-trifluoromethoxy-phenyl)-4-(3-methyl-4-nitro-benzyl)- 1 ,4-dihydro-tetrazol-5-one, l -(3-chloro-4-trifluoromethoxy-phenyl)-4-(3-methyl-4-mtro-benzyl)- 1 34-dihydro-tetrazol-5-one., l-(4-fluoro-3-üifluoromethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-lJ4-dihydro-tetrazol-5-one, l-(2-fluoro-5-1rifluoromethyl-phenyl)-4-(3-methyl-4-iiitro-benzyl)-lJ4-dihydro-tetrazol-5-one, l -(4-chloro-3-trifluoromethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)- 1 34-düi)'dro-tetrazol-5-one,,
l-(3,4-bis-trifluoromethyl-phenyI)-4-(3-methyl-4-iiitro-benzyl)-l,4-dihydro-tetrazol-5-one,
l-(3-fluoro-5-trifluoromethyl-phenyl)-4-(3-methyl-4-mtro-benzyl)-l,4-dihydro-tetrazol-5-one;
l-(3,5-dichloro-phenyl)-4-(3-methyl-4-nitro-benzyl)-l,4-dihydro-tetrazol-5-one.,
l-(3,5-dimethoxy-phenyl)-4-(3-methyl-4-nitro-benzyl)-l)4-dihydro-tetrazol-5-one,
l-(3,5-bis-trifluoromethyl-phenyl)-4-(2-ch]oro-4-nitro-benzyl)-l,4-dihydro-tetrazol-5-one,
l-(335-bis-trifluoromethyl-phenyl)-4-(3-ch]oro-4-nitro-benzyl)-l,4-dihydro-tetrazol-5-one;
l-(3J5-bis-trifluoromethyl-phenyl) -(3-methyl-4-nitro-benzyl)-l,4-dihydro-tetrazol-5-one)
l-(3,5-bis-trifluoromethyl-phenyl)-4-(2-methoxy-4-nitro-benzyl)-l,4-diliydro-tetrazol-5-one,
l-(3,5-bis-1rifluoromethyl-phenyl)-4-(3-methoxy-4-nitro-benzyl)-l;4-dihydro-tetrazol-5-one,
l-(3,5-bis-trifluoromethyl-phenyl)-4-(3.,5-dirnethyl-4-nitro-benzyl)-l,4-dihydro-tetrazol-5-one)
l-(3J5-bis-trifluoromethyl-phenyl)-4-[l-(3-methyl-4-nitro-phenyl)-ethyl]-l,4-dihydro-tetrazol-5-one,
l -(3-chloro-2-methoxy-5-meÜi3'l-phenyl)-4-(3 -methyl-4-nitro-benz)'l)- 1 -dihj o-tetrazol-S-one,
l-(2,2-difluoro-benzo[l,3]dioxol-5-yl)-4-(3-methyl-4-nitro-benzyl)-l,4-dihydro-tetrazol-5-oneJ
l-(3-methyl-4-nitro-benzyl)-4-(2,23J3-tetrafluoro-2;3-dihydro-benzo[l,4]dioxin-6-yl)-l34-dihydro-
tetrazol-5-one,
l -(3 -methyl-4-nitro-benzyl)-4-(2,2,3 -trifluoro-2,3 -dihydro-benzo[ l ,4] dioxin-6-yl)- 1 ,4-dihydro-
tetrazol-5-one,
l -(3 -methyl-4-nitro-benzyl)-4-(2,3 ,3 -trifluoro jS-dihydro-benzo [ l ,4] dioxin-6-yl)-l ,4-dihydro-
tetrazol-5-one,
l-(3-methyl-4-nitro-benzyl)-4-(232)333J7-pentafluoro-253-dihydro-benzo[l)4]dioxin-6-yl)-lJ4-

düiydro-tetrazol-5-one,
l-(3,5-dichloro-236-diethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-l,4-dihydro-tetrazol-5-one,
l -benzyl-4-(3 -methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5 -one,
l -(4-fluoro-benzyl)-4-(3 -methyl-4-nitro-benzyl)-134-dibydro-tetrazol-5-one,
l -(4-chloro-benz)'l)-4-(3-methyl-4-nitro-benzyl)-1 34-dihydro-tetrazol-5-one,
l -(3-methyl-4-nitro-benzyl)-4-(4-trifluoromethyl-benzyl)-1,4-dihydro-tetra2ol-5-one,
l -[ l -(2-fluoro-phenyl)-ethyl]-4-(3-methyl-4-nitro-benzyl)-134-dihydro-tetrazol-5-one,
l-[l-(2-cliloro-phenyl)-ethyl]-4-(3-methyl-4-nitro-benzyl)-l,4-dihydro-telTazol-5-oneJ
l-(3-methyl-4-nitro-benzyl)-4-[l-(2-1rifluoromethyl-phenyl)-eÜiyl]-lJ4-dihydro-tetrazol-5-one,
l-[l-(3-fluoro-phenyl)-ethyl]-4-(3-methyl-4-nitro-benzyl)-l)4-dihydro-tetrazol-5-one)
l - [ l -(3-chloro-phenyl)-ethyl]-4-(3 -methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5 -one:
l-(3-metliyl-4-nitro-benzyl)-4-[l-(3-trifluoromeÜayl-phenyl)-ethyl]-lJ4-dihydro-tetrazol-5-oneJ
l-[l-(4-fluoro-pb.enyl)-ethyl]-4-(3-methyl-4-nitro-benzyl)-l,4-dihydro-tetrazol-5-one,
l -[ l -(4-chloro-phenyl)-ethyl]-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,
l-(3-me(hyl-4-nitro-benz}d)-4-[l-(4-trifluoromethyl-phenyl)-ethyl]-l,4-dihydro-tetrazol-5-one,
l - [ l -(2,4-difluoro-phenyl)-ethyl]-4-(3-methyl-4-nitro-benzyl)-1 -dihydro-tetrazol-S-one,
l - [ l -(2,4-dichloro-phenyl)-ethyl]-4-(3 -methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,
l-[l-(3)4-difluoro-phenyl)-ethyl]-4-(3-meÜi}'l-4-nitro-benzyl)-l34-dihydro-tetrazol-5-one.
And as specific examples of the compounds of the formula (TV), starting materials in the preparation
process (b), there can be mentioned, for example,
2-{2-meth}d-4-[5-oxo-4-(2-cMoro-phenyl)-435-dmydro-tetrazol-l-ylmethyl]-phenyl}-isoindol-l,13-
dione-,
4-fluoro-2- {2-methyM-[5-oxo-4-(2-chloro-phenyl)-435-diliydro-tetrazol-1 -ylmethyl]-phenyl} -
isoindol-1,3-dione,
4-chloro-2-{2-methyl-4-[5-oxo-4-(2-chloro-phenyl)-435-dihydro-tetrazol-l-ylmethyl]-phenyl}-
isoindol-1,3-dione,
4-bromo-2- {2-methyl-4-[5-oxo-4-(2-chloro-phenyl)-4,5-dihydro-tetrazol-1 -ylmethylj-phenyl}-
isoindol-1,3-dione,
4-iodo-2- {2-methyl-4-[5 -oxo-4-(2-chloro-phen}'l)-4,5-dihydro-tetrazol-1 -ylmethyl] -phenyl} -isoindol-
1,3-dione,
4,7-dichloro-2-{2-methyl-4-[5-oxo-4-(2-chioro-phenyl)-435-dihydro-tetrazol-l-ylmet:hyl]-phenyl}-
isoindol-1,3-dione,
5,6-dicUoro-2-{2-me1hyl-4-[5-oxo-4-(2-cliloro-phenyl)-4,5-dih}'dro-tetrazol-l-ylmethyl]-phenyl}-
isoindol-l33-dione,
4-nitro-2-{2-methyl-4-[5-oxo-4-(2-chloro-phenyl)-4,5-dihydro-tetrazol-l-ylmethyl]-phenyl}-
isoindol-1,3 -dione,

4-methyl-2-{2-methyl-4-[5-oxo-4-(2-chloro-phen34)-4,5-dihydro-tetrazol-l-ylmethyl]-phen)4}-
isoindol-1,3-dione,
2- (2-methyl-4-[5 -oxo-4-(4-trifluoroinethyl-phenyl)-4,5-dihydro-tetrazol-1 -yknethyl] -phenyl} -
isoindol-1,3-dione,
4-fluoro-2-{2-me&yl-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-435-dihydro-tetrazol-l-yImethyl]-
phenyl}-isoindol-1,3-dione,
4-cUoro-2-{2-methyl-4-[5-oxo-4-(4-trifluoromeftyl-phenyl)-4,5-dihydro-tetrazol-l-ylmethyl]-
phenyl} -isoindol-1,3-dione,
4-bromo-2-{2-methyI-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-l-ylniet;hyl]-
phenyl}-isoindol-1,3-dione,
4-iodo-2-{2-me1±Lyl-4-[5-oxo-4-(4-trifluorome1hyl-phenyl)-4,5-dih)'dro-tetrazol-l-ylmethyl]-phenyl}-
isoindol-1,3-dione,
4,7-dichloro-2- {2-methyl-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1 -ylmethyl]-
phenyl}-isoindol-1,3-dione,
5,6-dicMoro-2-{2-methyl-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-l-ylmethyl]-
phenyl}-isoindol-1,3-dione,
4-ni1ro-2-{2-methyl-4-[5-oxo-4-(4-trifluoromet;hyl-phen}'l)-4,5-dihydro-tetrazol-l-ylmethyl]-
phenyl}-isoindol-1,3-dione,
4-me1iyl-2-{2-methyl-4-[5HDxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydTO-tetrazol-l-ylmel:hyl]-
phenyl} -isoindol-1,3-dione,
2-{2-methyl-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-l-ylmethyl]-phenyl}-
isoindol-l,3-dione.,
4-fluoro-2-{2-meth}4-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phenyl)-4,5-dihydro-tetra2ol-l-ylmeth3'l]-
phenyl} -isoindol-1,3-dione,
4-cMoro-2-{2-methyl-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phen)'l)-4,5-dihydro-tetrazol-l-ylmethyl]-
phenyl}-isoindol-1,3-dione,
4-bromo-2-{2-methyl-4-[5-oxo-4-(3,5-bis-tri'fluorome1:hyl-phen}d)-4,5-diliydro-tetrazol-l-ylmethyl]-
phenyl} -isoindol-1,3-dione,
4-iodo-2-{2-methyl-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-l-yknethyl]-
phenyl}-isoindol-1,3-dione,
4,7-dichloro-2- {2-methyl-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phenyl)-4,5 -dihydro-tetrazol-1 -
ylmethylj-phenyl} -isoindol-1,3-dione,
5,6-dichloro-2-{2-methyl-4-[5-oxo-4-(3,5-bis-trifl.uoromethyl-phenyl)-4,5-dihydro-tetrazol-l-
ylmethylj-phenyl} -isoindol-1,3-dione,
4-nitro-2-{2-methyl-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-l-ylmethylj-
phenyl} -isoindol-1,3 -dione,
4-metyl-2-{2-methyl-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phenyl)-4,5-dih)'dro-tetrazol-l-ylniethyl]-

phenyl} -isoindol-1,3-dione.
The compounds of the formula (V), starting materials in the preparation process (b), are either well-known compounds in the field of organic chemistry or can be synthesižed according to the process described in DE-A 20 45 905, WO 01/23350 ete. As their specific examples there can be mentioned ethylamine, diethylamine, n-propylamine, isopropylamine, n-butylamine, sec-butylamine, isobutyl-amine, t-butylamine, t-amylamine, cyclopropylamine, cyclopentylamine, cyclohexylamine, 3-methyl-cyclohexylamine, 2-(methylthio)-ethylamine, 2-(ethyltMo)-emylamine, l-methyl-2-(methylthio)-ethylamine, l,l-dimethyl-2-(methylthio)-ethylamine, ete.
Compounds of the formula (VI), starting materials in the preparation process (c), include known
compounds or can be easily' obtained according to the process described in EP-A 0919 542, EP-A
l 006 107 ete. and as their specific examples there can be mentioned,
N-isopropyl-phthalamic acid,
3 -fiuoro-N-isopropyl-phthalamic acid,
3 -chloro-N-isopropyl-phthalamic acid,
3 -bromo-N-isopropyl-phthalamic acid,
3-iodo-N-isopropyl-phthalamic acid,
N-isopropyl-3-nitro-phthalamic acid, .
N-(l -methyl-2-methylsulfanil-ethyl)-phthalamic acid,
3-fiuoro-N-(l -methyl-2-methylsulfanil-ethyl)-phthalamic acid,
3-chloro-N-(l-methyl-2-methylsulfanil-ethyl)-phthalamic acid,
3-bromo-N-( l -methyl-2-metliylsulfanil-ethyl)-phtiialamic acid,
3-iodo-N-( l -methyl-2-methylsulfanil-ethyl)-phthalamic acid,
N-(l-memyl-2-memylsulfanil-eth.yl)-3-nitro-phthalamic acid,
N-( l, l -dimethyl-2-methylsulfanil-ethyl)-phthalamic acid,
N-(l,l-dimethyl-2-methylsulfanü-ethyl)-3-fluoro-phthalamic acid,
3-chloro-N-( l, l -dimethyl-2-methylsulfanil-ethyl)-phthalamic acid,
3-bromo-N-(l,l-dimethyl-2-methylsulfanil-ethyl)-phthalamic acid,
N-( l, l -dimethyl-2-methylsulfanil-ethyl)-3 -iodo-phthalamic acid,
N-( l, l -dimethyl-2-methylsulfanil-ethyl)-3 -nitro-phthalamic acid,
N-isopropyl-3 -methanesulfonyloxy-phthalamic acid,
N-( l -memyl-2-methylsulfanil-ethyl)-3-methanesulfonyloxy-phthalamic acid,
N-( l, l -dimethyl-2-methylsulfanil-ethyl)-3 -methanesulfonyloxy-phthalamic acid.
The compounds of the above-mentioned formula (VT) can be easily obtained generally by reacting phthalic anhydrides of the formula

(Figure Removed) wherein X and n have the same definition as aforementioned,
and amines of the formula
(Figure Removed)wherein R1 and R2 have the same definition as aforementioned.
The above-mentioned compounds of the formula (XIH) and the cpmpounds of the formula (XIV) are all well-known in the field of organic chemistry and specifically there can be mentioned the following as examples.
As examples of the compounds of the formula (XEET) there can be mentioned, phthalic anhydride, 3-fluorophthalic anhydride, 3-chlorophthalic anhydride., 3-bromophmalic anhydride, 3-iodophthalic anliydride, 3-methylphthalic anhydride, 3-nitrophthalic anhydride., 3,6-di-fluorophthalic anhydride, 3,6-dichlorophthalic anhydride, 4,5-dichlorophthalic anhydride, 3,4,5,6-tetrafluorophthalic anhydride, 3,4,5,6-tetrachlprophthalic anhydride, 3-methanesulfonyloxyphtlialic anhydride.
As examples of the compounds of the formula (XIV) there can be mentioned,
ethylamine, n-propylamine, isopropylamine, n-butylamine, sec-butylamine, isobutylamine, t-butyl-
amine, t-amylamine, cyclopropylamine, cyclopentylamine, cyclohexylamine, 2-(metli3'lthio)-ethyl-
amine, 2-(ethylthio)-ethylamine, l-methyl-2-(methyltlTio)-ethylamine, l,l-dimethyl-2-(methylthio)-
ethylamine.
These amines can be easily obtained also by the process described in DE-A 20 45 905, WO 01/23350.
The reaction for synthesizing the compounds of the formula (VT) can be conducted according to the process described Org. Chem. 1981,46,175 ete.
Such a reaction can be conducted in an adequate diluent and as examples of the diluent used in that case there can be mentioned aliphatic, alicyclic and aromatic hydrocarbons (may be optionally chlori-nated), for example, pentane, hexane, cyclohexane, petroleum ether, ligroine, benzene, toluene,
xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, dichlorobenzene; ethers, for example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF), dietiiylene glycol dimethyl ether (DGM); ketones, for example, acetone, methyl ethyl ketone (MEK), methyl isopropyl ketone, methyl isobutyl ketone (MffiK), ete.; nitriles, for example, acetonitrile, propionitrile, acrylonitrile; esters, for example, ethyl acetate, amyl acetate.
The preparation process (e) can be conducted in the presence of a base and as such a base there can be mentioned tertiary amines, dialkylaminoanilines and pyridines, for example., triethylamine, 1,1,4,4-tetramethyleÜiylenediamine (TMEDA), N,N-dime1hylaniline, N,N-diethylaniline, pyridine, 4-dimethylaminopyridine (DMAP), l,4-diazabicyclo[2.2.2]octane (DABCO) and 1,8-diazabi-cyclo[5.4.0]undec-7-ene (DBU), ete.
The reaction can be conducted in a substantially wide range of temperature. It can be conducted at the temperatures in a range of generally about -70°C to about 100°C, preferably about 50°C to about
- V
80°C. Although said reaction is conducted desirably under normal pressure, it can be operated also under elevated pressure or under reduced pressure.
In conducting the reaction., the aimed compounds can be obtained, for example, by reacting l mole amount to 4 mole amount of the compounds of the formula (XIV) to l mole of the compounds of the formula (Xm) in a düuent, for example, acetonitrile.
The compounds of the formula (VII), starting materials in the preparation process (d), are novel compounds and can be easily obtained, for example, by reacting a compound represented by the formula (VHI-a)
(Figure Removed)wherein X, n, A1, r, Q, A2, s and E have the same definition as aforementioned., in the presence of a condensing agent (cf. e.g. J. Med. Chem. 1967,10, 982).
The compounds of the above-mentioned formula (VHI-a) are also novel compounds and can be easily obtained by reacting phthalic anhydrides of the aforementioned formula (X) and the compounds of the aforementioned formula (DI), in which R3 is a hydrogen atom.

The above-mentioned reaction of a compound of the formula (VIE-a) and a compound of the formula (KT), in which R3 is a hydrogen atom, can be conducted in an adequate diluent and as examples of the diluent used in that case there can be mentioned aliphatic, alicyclic and aromatic hydrocarbons (may be optionally chlorinated), for example, pentane, hexane, cyclohexane, petroleum ether, ligroine, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, dichlorobenzene; ethers, for example, ethyJ ether, methy] ethyl ether, isopropyi etnsr, buryl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (TH#), dierh,vl*» The reaction can be conducted in the presence of ,a base and as such a base there can be mentioned tertiary amines, dialkykia-incaniH. c-s mid pyriüines, for example, trieüaylamine, 1,1,4,4-tetramethyl-ethylenediamine (TMEDA), N,N-dimethylaniline, N,N-diethylaniline, pyridine, 4-dimethylami-nopyridine (DMAP), l,4-diazabicyclo[2.2.2]octane (DABCO) and l,S-diazabicyclo[5.4.0]undec-7-ene(DBU).
The reaction can be conducted in a substantially wide range of temperature. It can be conducted at the temperatees in a range of generally about -70°C to about 100°C, preferably about -50°C to about 80°C.
Although said reaction is conducted desirably under nomial pressure, it can be operated also under elevated pressure or under reduced pressure.
In conducting the reaction, the aimed compounds can be obtained, for example, by reacting l mole amount to 4 mole amount of the compounds of the formula (ffl), in which R3 is a hydrogen atom, to l mole of the compounds of the formula (X) in a diluent, for example, acetonitrile.
As specific examples of the compounds of the above-mentioned formula (Vm-a), there can be
mentioned, for example,
N. {4-[4-(2-chloro-phenyl)-5-oxo-4,5-dihydro-tetrazol-1 -yknethyl]-2-methyl-phenyl} -6-iodo-
phthalamic acid, 6-iodo-N-{2-memyl-4-[5-oxo-4-(2-1rifluoromemyl-phenyl)-4,5-dihydro4etrazol-l-yh3iethyl]-
phenyl}-phfhalamic acid,
N-{4-[4-(4-fluoro-phenyl)-5-oxo-4,5-düiydro-te1razol-l-ylmeth.yl]-2-methyl-phenyl}-6-iodo-phthalamic acid,

N-{4-[4-(4-cHoro-phenyl)-5-oxo-435-dihydro-tetrazol-l-ykQeihyl]-2-methyl-phenyl}-6-iodo-.phthalamic acid,
6-iodo-N-{2-methyl-4-[5-oxo-4-(4-trifluorometliyl-phenyl)-4,5-düiydro-tetrazol-l-ylmethyl]-phenyl} -phthalamic acid, ete.
examples of the compounds of the ahove-mentioned formula (VII), there can be
aihy dro-tetrazol-5 -one, !-(4-chloro-phenyl)-4-[4-(4-iodo-3-oxo-3H-isobenzofuran-l-ylideneainino)-3-me1hyl-beiizyl]-l34-
dihydro-tetrazol-5-one,
\? l -[4-(4-iodo-3 -oxo-3H-isobenzofuran- 1 -ylideneamino)-3 -methyl-benzyl]-4-(4-trifluoromethyl-
phenyl)-l,4-dihydro-tetrazol-5-one., ete.
The compounds of the formula (V), also starting materials in the preparation process (d), have been described in the aforementioned preparation process (b).
The compounds of the formula O'7!!!)» starting materials in the preparation process (e), are compounds and can be easily obtained, as described 'in the aforementioned preparation process (d), generally by reacting phthalic anhydrides of the aforementioned formula (X) with the compounds of the aforementioned formula (TÜ).
The reaction is the same as already described in the aforementioned preparation process (d).
As specific examples of the compounds of the formula (VUI) there can be mentioned, N-{4-[4-(2-chloro-phenyl)-5-oxo-4,5-dihydro-tetrazol-l-yknethyl]-2-methyl-phenyl}-N-methyl-6-iodo-phthalamic acid,
6-iodo-N-{2-methyl-4-[5-oxo-4-(2-trifluoromethyl-phenyl)-4,5-dmydro-tetrazol-l-y]methyl]-phenyl} -N-methyl-phthalamic acid,
N-{4-[4-(4-fluoro-phenyl)-5-oxo-4,5-dmydro-tetrazol-l-ylmethyl]-2-methyl-phenyl}-N-methyl-6-iodo-phthalamic acid,
N-{4-[4-(4H3Horo-phenyl)-5-oxo-4,5-dihydro-terrazol-l-ylrnethyl]-2-methyl-phenyl}-N-methyl-6-iodo-phthalamic acid,
6-iodo-N-{2-methyl-4-[5-oxo-4-(4-trifluoromemyl-phenyl)-455-dihyoro-te1razol-l-ylmethyl]-N-methyl-phenyl}-phthalamic acid.
The compounds of the formula (V), also starting materials in the preparation process (e), are identical with those in the aforementioned preparation processes (b) and (d).
As another preparation process for the compounds of the aforementioned formula (VIU), the common starting materials in the preparation process (d) and preparation process (e), in which X and Y represent other groups than bromo or iodo, compounds of the formula
(Figure Removed)wherein n, R3, m, A1, r, Q, A2, s and E have the same definition as aforementioned, and
X1 and Y1 each has a definition of the aforementioned X and Y but excluding bromo and iodo,
is reacted with a metal reagent, for example, butyl lithium, and then reacted with carbon dioxide to
obtain the compounds of the corresponding formula (VTD) (however, X and Y do not represent
bromo or iodo).
The compounds of the above-mentioned formula (XV) are novel compounds and can be easily obtained generally by reacting a benzoic acid halide represented by the formula
(Figure Removed)wherein X1 and n have the same definition as aforementioned, and Hai represents a halogen atom, with the compounds of the aforementioned formula (DI)
(Figure Removed)wherein R3, Y, m, A1, r, Q, A2, s and E have the same definition as aforementioned.
The compounds of the above-mentioned formula (XVI) are well-known compounds in the field of organic chemistry and there can be mentioned specifically,
benzoyl chloride, 3-fluorobenzoyl chloride, 3-chlorobenzoyl chloride, 3-methylbenzoyl chloride, 3-nitrobenzoyl chloride.
The reaction to prepare the compounds of the above-mentioned formula (XV) can be conducted in an adequate diluent and as examples of tlie diluent used in that case there can be mentioned aliphatic, alicyclic and aromatic hydrocarbons (may be optionally chlorinated), for example, pentane, hexane, cyclohexane, petroleum ether, ligroine, benzene, toluene, xylene, -dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, dichlorobenzene; ethers, for example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF),- diethylene glycol dimethyl ether (DGM); esters, for example, ethyl acetate, amyl acetate.
The reaction can be conducted in the presence of an acid binder and as such an acid binder there can be mentioned, as inorganic base, hydroxides, carbonates, bicarbonates, ete. of alkali metals and alkaline earth metals, for example, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate., potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide; as organic base, alcoholates, tertiary amines, dialkylaminoanilines and pyridines, .for example, triethylamine, 1,1,4,4-teträmethylethylenediamine (TMEDA), N,N-dimethylaniline, N5N-diethylaniline, pyridine, 4-dimethylaminopyridine (DMAP), l,4-diazabicyclo[2.2.2]octane CDABCO) and l,8-diazabicyclo[5.4.0]undec-7-ene (DBU).
The reaction can be conducted in a substantially wide range of temperature. It can be conducted at the temperatures in a range of generally about-20 to about 150°C, preferably about 0°C to about 100°C.
Although said reaction is conducted desirably under normal pressure, it can be operated also under elevated pressure or under reduced pressure.
In conducting the reaction, the aimed compounds can be obtained, for example, by reacting l mole amount to a little excess amount of the compounds of the formula (DI) to l mole of the compounds of the formula (XVI) in a diluent, for example, 1,2-dichloroethane, in the presence of triethylamine.
The compounds of the formula (Ii), starting materials in the preparation process (f), are the compounds included in the aforementioned formula (I) of the present invention. By oxidizing C1-C6-allcylthio-C1-C6-alkyl, the definition of RIf in the formula (If), compounds of the formula (I) corresponding to C1-C6-alkylsulfüiyl-C1-C6-alkyl or Ci-Cä-alkylsulfonyl-C1-C6-alkyl canbe obtained.
The compounds of the formula (If) can be prepared by the aforementioned preparation processes (a), (b),(c),(d)and/or(e).
As specific examples of the compounds of the formula (If) there can be mentioned, for example,
3-iodo-N2-(l-methyl-2-methylsulfanyl 4,5-dihydro-triazol-l-ylmethyl]-phenyl}-phtiialamide,
phenyl)-4,5-dihydro-triazol- 1 -ylmethylj-phenyl} -phthalamide,
3-iodo-N2-(l-methyl-2-methylsulfanyl-ethyl)-N1-{2-me%l-4-[5-oxo-4-(4-1rifluoromethyl-phenyl)-4,5-dmydro-triazol-l -ylmethyl]-phenyl} -phthalamide,
N2-(l,l-dimethyl-2-methylsulfanyl-ethyl)-3-iodo-N1-{2-methyl-4-[5-oxo-4-(4-trifluoromethyl-phenyl) -4.,5-dihydro-triazol- 1 -ylmethyl] -phenyl} -phthalamide,
N1-{4-[4-(3]5-bis-tiifluoromemyl-phenyl)-5-oxo-4,5-dihydro-triazol-l-ylmethyl]-2-methyl-phenyl}-3-iodo-N2-(l-methyl-2-methylsulfanyl-eÜayl)-phthalamide,
NI-{4-[4-(3,5-bis-trifluoromemyl-phenyl)-5-oxo-4,5-dihydro-1xiazol-l-ylme1hyl]-2-methyl-phenyl}-N2-(l , l -dimethyl-2-methylsulfanyl-ethyl)- 3-iodo-phthalamide, ete.
The reaction of the aforementioned preparation process (a) can be conducted by using adequate diluents, singly or mixed, and as examples of the diluents used in that case there can be mentioned water; aliphatic, alicyclic and aromatic hydrocarbons (may be optionally chlorinated), for example., pentane, hexane, cyclohexane, petroleum ether, ligroine, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, dichlorobenzene; ethers, for example, ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane, ditnethoxyethane (DME), tetrahydrofuran (THF), diethylene glycol dimethyl ether (DGM); nitriles, for example, . acetonitrile, propionitrile, acrylonitrile; esters, for example, ethyl acetate, amyl acetate.
The preparation process (a) can be conducted in the presence of an acid catalyst and as examples of such an acid catalyst there can be mentioned mineral acids, for example, hydrochloric acid, sulfuric acid, organic acids, for example, acetic acid, trifluoroacetic acid, propionic acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid.
The preparation process (a) can be conducted in a substantially wide range of temperature. It can be conducted at the temperatees in a range of generally about -20°C to about 100°C, preferably about 0°CtoaboutlOO°C.
Although said reaction is conducted desirably ünder normal pressure, it can be operated also under elevated pressure or under reduced pressure.
In conducting the preparation process (a), the aimed compounds can be obtained, for example, by reacting l mole amount to a little excess amount of the compounds of the formula (IH) to l mole of
the compounds of the formula (ü) in a diluent, for example, 1,2-dichloröethane, in the presence of 0.01-0.1 mole aniount of p-toluenesulfonic acid.
The preparation process (b) can be conducted in the presence of a base such as tertiary amines, dialkylaminoanilines and pyridines, for example, Iriethylamine, 1,1,4,4-telramethylethylenediarnine (TMEDA), N,N-dimethylaniline, N,N-diethylaniline, pyridine, 4-drmethylaminopyridine (DMAP), l,4-diazabicyclo[2.2.2]octane (DABCO) and l,8-diazabicyclo[5.4.0]undec-7-ene (DBU), ete. '
The preparation process (b) can be conducted in a substantially wide range of temperature. It can be conducted at the temperatures in a range of generally about -20°C to about 150°C, preferably room temperature to about 100°C. Although said reaction is conducted desirably under normal pressure, it can be operated also under elevated pressure or under reduced pressure.
In conducting the preparation process (b), the aimed compounds can be obtained, for example, by reactmg l mole amount to 25 mole amount of the compounds of the formula (V) to l mole of the compounds of the formula (IV).
The aforementioned preparation processes (c), (d) and (e) can be conducted under the similar conditions as for the above-mentioned preparation process (a).
The reaction of the aforementioned preparation process (f) can be conducted in an adequate diluent and as examples of the diluents used in that case there can be mentioned aliphatic, alicyclic and aro-matic hydrocarbons (ma}' be optionally chlorinated), for example, benzene, toluene, xylene, dichloro-methane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, dichlorobenzene; alcohols, for example, methanol, ethanol, isopropanol, butanol, acids: formic acid, acetic acid.
As oxidizing agent to be used there can be mentioned, for example, metachloroperbenzoic acid, peracetic acid, potassium metaperiodate, potassium hydrogen persulfate (oxone), hydrogen peroxide.
The preparation process (i) can be conducted in a substantially wide range of temperature. It can be
conducted at the temperatures in a range of generally about —50°C to about 150°C, preferably about —
10°CtoaboutlOO°C.
Although said reaction is conducted desirably under normal pressure, it can be operated also under
elevated pressure or under reduced pressure.
In conducting the preparation process (f), the aimed compounds can be obtained, for example, by reactrng l mole amount to 5 mole amount of an oxidizing agent to l mole of the compounds of the formula (Ii) in a diluent, for example, dichloromethane.
The reaction of the preparation process (f) can be conducted according to the process described in, for example, Jildcen Kagaku Kohza (Lectures of experimental chemistry), compiled by the Chemical Society of Japan, 4* ed., Vol. 24, page 350 (1992) published by Maruzen or ibid., page 365.
The compounds of the formula (I) of the present invention show strong insecticidal action. They can, therefore, be used. as insecticidal agents. And the active compounds of the formula (I) of the present invention exhibit exact controlling effect against harrnful insects without phytotoxicity against cultured plants. The compounds of the present invention can be used for controlling a wide variety of pests, for example, harmful sucldng insects, biting insects and other plant-parasitic pests, stored grain pests, hygienic pests, ete. and applied for their exterrhination.
As examples of such pests there can be mentioned the following pests:
As insects, there can be mentioned coleoptera pests, for example, Callosobruchus Chinensis,
Sitophilus zeamais, Tribolium castaneum, Epilachna vigintioctomaculata, Agriotes fuscicollis,
Anomala rufocuprea, Leptinotarsa decemlineata, Diabrotica spp., Manochamus alternatus,
Lissorhoptrus oryzophüus, Lyctus bruneus;
Lepidoptera pests, for example, Lymantna dispar, Malacosoma neustria,- Pieris rapae, Spodoptera
h'tura, Mamestra brassicae, Chilo suppressalis, Pyrausta nubilalis, Ephestia cautella, Adoxophyes
orana, Carpocapsa pomonella, Agrotis fucosa, Galleria mellonella, Plutella maculipennis., Heliothis
virescens, Phyllocnistis citrella;
Hemiptera pestc, for e?;ample, Nephotettix cincticeps, Nilaparvata lugens, Pseudococcus comstocki,
Unaspis yanonensis, Myzus percicae, Aphis pomi, Aphis gossypii, Rhopalosiphum pseudobrassicas,
Stephanitis nashi, Nazara spp., Cimex lectularius, Trialeurodes vaporariorum, Psylla spp.;
Orthoptera pests, for example, Blat&lla germanica, Periplaneta americana, Gryllotalpa qfriccaia,
Locusta migi-atoria migrqtoriodes;
Homoptera pests, for example, Reticulitermes speratiis, Coptotermesformosanus;
Diptera pests, for example, Musca domestica, Aedes aegypti, Hylemia platura, Culex pipieiis,
Anopheles slnensis, Culex fritaeniorhynchus.
Moreover, as mites there can be mentioned, for example, Tetranychus telcains, Tetranychus urticae,
Panonyclms citri, Aculops pelekassi, Tarsonemits spp.
Furthermore, as nematodes there can be mentioned, for example, Meloidogyne incognita,
Bursaphelenchus lignicolus Mamiya et Kiyohara, Aphelenchoides basseyi, Heterodera glycines,
Pratylenchus spp.
In addition, in the field of veterinary medicine, the novel compounds of the present invention can be effectively used against various harmful animal-parasitic pests (endoparasites and ectoparasites), for
example, insects and helminthes. As examples of such anirnal-parasitic pests there can be mentioned the following pests:
As insects there can be mentioned, for example, Gastrophilus spp., Stomoxys spp., Trichodectes spp.,
Rhodnius spp., Ctenocephalides canis.
As mites there can be mentioned, for example, Ornithodoros spp., hodes spp., Boophilus spp.
In the present invention substances häving insecticidal action against pests, which indude all of them, are in some cases called as insecticides.
The active compounds of the present invention can be made into customary formulation forms, when they are used as insecticides. As formulation fonns there can be mentioned, for example, sohitions, emulsions, wettable powders, water dispersible granules, suspensions, powders, foaming agents, pastes, tablets, granules, aerosols, active compound-impregnated natural and synthetic substances, rnicrocapsules, seed coating agents, formulations used with buming equipment (as burning equipment, for example, fumigation and smoking cartridges, cans, coils, ete.), ULV [cold mist, warm mist], ete.
These formulations can be prepared according to per se known methods, for example, by mixing the active compounds with extenders, namely liquid düuents; liquefied gas diluents; solid diluents or carriers, and optionally by using surface-active agents, namely emulsifiers and/or dispersants and/or foam-forming agents.
In case that water is used as extender, for example, organic solvents can be used also as auxiliary solvents.
As liquid diluents or carriers there can be mentioned, for example, aromatic hydrocarbons (for example, xylene, toluene, alkylnaphthalene ete.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (for example, clllorobenzenes, ethylene chlorides, methylene chloride, ete,), aliphatic hydrocarbons [for example, cyclohexane ete. or paraffins (for example, mineral oil fractions ete.)], alcohols (for example, butanol, glycols and their ethers, esters, ete.), ketones (for' example., acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, ete.), strongly polar solvents (for example, dimethylformamide, dimethyl sulfoxide, ete.), and water.
Liquefied gas diluents or carriers are substances that are gases at nonnal temperature and pressure and there can be mentioned, for example, aerosol propellants such as butane, propane, nitrogen gas, carbon dioxide, halogenated hydrocarbons.
As solid diluents there can be mentioned, for example, ground natural minerals (for example, kaolin, clay, taie, chalk, quartz, attapulgite, montmorillonite, diatomaceous earth, ete.), ground synthetic minerals (for example, highly dispersed süicic acid, alumina, silicates, ete.).
As solid carriers for granules there can be mentioned, for example, crushed and fractionated rocks (for example, -calcite, marble, pumice, sepiolite, dolomite, ete.) synthetic granules of inorganic and organic meals, partides of organic materials (for example, saw dust, coconut shells, maize cobs, tobacco stalks, ete.) ete.
As emulsifiers and/or foam-forming agents there can be mentioned, for example, noniomc and anionic emulsifiers [for example, polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (for example, alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates, ete.)], albumin hydrolysis products, ete.
Dispersants include, for example, lignin sulfite waste liquor and methyl cellulose.
Tacldfiers can also be used in formulations (powders, granules, eraulsifiable concentrates). As said taclafiers there can be mentioned, for example, carboxymethyl cellulose, natural and synthetic polymers (for example, gum Arabic, polyvinyl alcohol, polyvinyl acetate, ete.).
Colorants can also be used. As said colorants there can be mentioned, for example, inorganic pigments (for example, iron oxide, titanium oxide, Prussian Blue, ete,), organic dyestuffs such as alizarin d)'estuffs, azo dyestuffs or rnetal phthalocyanine dyestuffs, and further traces nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
Said formulations can contain the aforementioned active components of the amount in the range of generally 0.1-95 % by weight, preferably 0.5-90 % by weight.
The active compounds of Üae formula (I) of the present invention can exist also as a mixed agent with other active compounds, for example, insecticides, poisonous baits, bactericides, miticides, nematicides, fungicides, growth regulators or herbicides in the form of their commercially usefül formulations or in tlie application forms prepared from such formulations. Here, as the above-mentioned insecticides, there can be mentioned, for example, organophosphorous agents, carbamate agents, carboxylate type chemicals, chlorinated hydrocarbon type chemicals, insecticidal substances produced by microbes, ete.
Further, the active compounds of the formula (I) of the present invention can exist also as a mixed agent with a synergist and such formulations and application forms can be mentioned as commercially useful. Said synergist itself must not be active, but is a compound that enhances the action of the active compound.
The content of the active compounds of the formula (T) of the present invention in a commercially useful application form can be varied in a wide range.
The concentration of the active compounds of the formula (I) of the present invention at the time of application can be, for example, in the range of 0.0000001-100 % by weight, preferably in the range of 0.00001-1 %by weight.
The compounds of the formula (I) of the present invention can be used by usual methods suitable to the application forms.
In case of application against hygienic pests and stored grain pests the active compounds of the present invention have a good stability against alkali on a calcific substance and further show an excellent residual effectiveness in wood and soil.
Then the present invention will be described more specifically by examples. The present invention, however, should not be restricted only to them in any way.
Examples
Synthesis Example l

(Figure Removed)3-(l,l-Dimethyl-2-meAylthioetiiyliinino)-4-iodo-3H-isoBenzofuran-l-öne (0.94g) and l-(4-amino-3-memylbenzyl)-4-(4-trifluoromethylphenyl)-l,4-dihydrotetrazol-5-one (0.87 g) were dissolved in dichloromethane (10 ml), to which p-toluenesulfonic acid monohydrate (0.01 g) was added, and the mixture was stirred at room temperature for 3 hours. After finishing the reaction, water was added to the mixture and the organic layer was separated'and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography to obtain N2-(l,l-dimethyl-2-methyltiiioethyl)-3-iodo-NI-[2-methyl-4-(5-oxo-4-(4-trifluoromethylphenyl)-435-dihydrotetrazol-l-ykaethyl)phenyl]phthalarnide (0.6 g, mp. 83-87°C).
Synthesis Example 2

(Figure Removed)NI-{4-[4-(3,5-bis-trifluoromethylphenyl)-5-oxo-4,5-dihydrotetrazol-l-ylrneÜiyl]-2-methyl-phenyl}-N2-(l,l-dimeäiyl-2-methyltlTioethyl)-3-iodo-phthalamide (0.5 g) was dissolved in dichloromethane, to which m-chloroperbenzoic acid (0.18 g) was added, and the mixture was stirred at room temperature for 5 hours. After finishing the reaction the mixture was washed successively with aqueous solution of sodium thiosulfate, saturated aqueous sohition of sodium hydrogen earbonate and saturated aqueous solution of sodium chloride and dried with anhydrous magnesium sulfate. After the solvent was distilled off, the obtained residue was purified by silica gel column chromatography to obtain N1-{4-[4-(3)5-bis-trifluoromemylphenyl)-5-oxo-435-dihydrotetrazol-l-ylmethyl]-2-methyl-phenyl}-3-iodo-N2-(2-methanesdfmyl-l3l-dimethylethyl)phthalamide (0.1 g, mp. 165-171°C).

Synthesis Example 3

(Figure Removed)N2-(14-Dimethyl-2-methylthioethyl)-3-iodo-
dihydrotetrazol-l-ylmethyl)phenyl]phthalamide (0.4 g) was dissolved in dichloromethane, to which m-chloroperbenzoic acid (0.24 g) was added, and the mixture was stirred at room temperature for 5 hours. After finishing the reaction the mixture was washed successively with aqueous solution of sodium thiosulfate, saturated aqueous solution of sodium hydrogen cafbonate and saturated aqueous solution of sodium chloride and dried with anhydrous magnesium sulfate. After the solvent was distilled off, the obtained residue was purified by silica gel column chromatography to obtain 3-iodo-N2-(2-methanesulfonyl-1, l -dimethylethyH-N1- {2-methyl-4-[5-oxo-4-(4-trifluoromethylphenyl)-4)5-dihydrotetrazol-l-yknethyl]phenyl}phthalamide (O.ldfg, mp. 108-112°C).
Synthesis Example 4
(Figure Removed)2-{2-Methyl-4-[5-oxo-4-(4-1rifluoromethylphenyl)-4,5-dihydrote1razol-l-ylmethyl]phenyl}isomdol-1,3-dione (0.25 g) was dissolved in sec-butylamine (5 ml) and the mixture was stirred at room temperature for 5 hours. After finishing the reaction, the solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography to obtain the öbjected N-sec-but5d-N-{2-methyl-4-[5-oxo-4-(4-trifluoromethylphenyl)-4,5-dihydrotetrazol-l- yl-methyl]phenyl}phthalamide (0.2 g, mp. 217-218°C).
Examples of the compounds of the formula (T) of the present invention obtained in the simüar manner to the Synthesis Examples l to 4 and the compounds of the formula (!) obtained easily by the preparation processes (a) to (f) are shown in the Table l to Table 4, together with the compounds obtained in the above-mentioned Synthesis Examples l to 4.
In all tables the abbreviations mean
Ph = phenyl, Me = methyl, Et = ethyl, n-Pr = n-propyl, i-Pr = iso-propyl.
Tablel(r = Q. s =)
(Figure Removed)
(Table Removed)Q represents the following structures:
(Figure Removed) (wherein the bond märked with * connects with A1 and the bond märked with # connects with A2)
Table2(i=l,s=0)

Q represents the following structures:
(Table Removed)
Q represents the following structures:
(Figure Removed) (wherein the bond märked with * connects with A1 and the bond märked with # connects with A2)
(Table Removed)Table 4(i=l. s=l)
Q represents the following structures: O

(Table Removed)
Synthesis Example 5 (Starting Materjal Synthesis)
(Figure Removed)To an ethanol solution (100 mL) of l-(3-mefeyl-4-nitrobenzyl)-4-(4-trifluoromethylphenyl)-l,4-dihydrotetrazol-5-one (9.4Sg) 10% palladium carbon (0.25g) was ädded and the mixture was stirred under hydrogen atmosphere at room temperature for 6 hours. After finishing tiie reaction, palladium carbon was filtered off and the solvent was distilled off under reduced pressure to obtain l-(4-amino-3-methyl-benzyl)-4-(4-trifluoromethyl-phenyl)-l,4-dihydrotetrazol-5-one (8.1 1 g, mp. 210-21 1 °C).
Synthesis Example 6 (Starting Material Synthesis)

(Figure Removed)In a similar manner as Synthesis Example 5, by using l-(3-niethyl-4-mtro-benzyl)-4-(3~trifluoro-methylphenyl)- 1 ,4-dihydrotetrazbl-5-one, l -(4-arnino-3-methyl-benz3'l)-4-(3-trifluoromethyl-phe-nyl)-l,4-dihydrotetrazol-5-one was obtained (mp. 89-94°C).
Synthesis Example 7 (Starting Material Syntfaesis)

(Figure Removed)In a similar manner as Synthesis Example 5, by using l-(3,5-bis-trifIuoromethyl-phenyl)-4-(3-me-thyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one, l -(4-amino-3 -methyl-benzyl)-4-(3,5-bis-trifiuoro-methyl-phenyl)-l,4-dihydro-tetrazol-5-one was obtained (mp. 129-130°C).
Synthesis Example 8 (Starting Material Synthesis)
(Figure Removed)3-Methyl-4-nitrobenzyl chloride (1.6 g), l-(4-trifluoromethylphenyl)-l,4-dihydrotetrazol-5-one (2.0 g) and potassium carbonate (1.4 g) w.ere stirred in DMF (50 ml) at room temperature for 5 hours.

After finishing the reaction, water (100 ml) was added and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride (100 ml) and dried with magnesium sulfate. After the solvent was distilled off, the obtained residue was purified by silica .gel column chromatography to obtairi l-(3-methyl-4-iütrobenzyl)-4-(4-tri-fluoromethylphenyl)-l,4-dihydrotetrazol-5-one [2.6 g, 'H-NMR (CDC13, ppm) ; 2.6 (3H, s), 5.3 (2H, s), 7.4-8.3 (7H, m)].
Synthesis Example 9 (Starüng Materjal Synthesis)
(Figure Removed)In a similar manner as Synthesis Example 8, by usingi-(3-trifluoromethyl-phenyl)-l,4-düiydro-te1ra-zol-5-one, l-(3-methyl-4-nitro-benzyl)-4-(3-trifluoromethyl-phenyl)-l34-dihydrotetrazol-5-one was
obtained ['H-NMR (CDC13, ppm) ; 2.6 (3H, s), 5.2 (2H, s), 7.3-8.2 (7H, m)].
Synthesis Example 10 (Starting Materjal Synthesis)
(Figure Removed)In a similar manner as Synthesis Example 8, by using l-(3,5-bis-trifluoromemyl-phenyl)-l,4-dilrydro-tetrazol-5-one in place of l-(4-trifluoromethyl-phenyl)-l,4-dihydro-tetrazol-5-one, l-(3,5-bis-trifluoromethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-l,4-dihydro-teti-azol-5-one was obtained [:H-NMR (CDC13, ppm); 2.6 (3H, s), 5.2 (2H, s), 7.2-8.0 (4H, m), 8.5 (2H, bs)j.
Synthesis Example 11 (Starting Materjal Synthesis)
(Figure Removed)3,5-Bis(trifluoromethyl) phenyl isocyanate (10.20 g) and trimethylsilyl azide (9.36 g) were stirred at 120-130°C for 10 hours. After the reaction mixture was brought to the room temperature, excess of trimethylsilyl azide was distilled off under reduced pressure and the obtained erude crystals were washed with petroleum ether to obtain l-(3,5-bis-trifluoromethyl-phenyl)-l,4-dihydro-tetrazol-5-one (11.05g,mp. 145-147°C).
Synthesis Example 12 (Starting Materjal Synthesis)
(Figure Removed)Phthalic anhydride (1.0 g) and l-(4-amino-3-methylbenz}4)-4-(4-trifluoromethylphenyl)-l,4-dihydro-tetrazol-5-one (2.4 g) were refluxed in 60ml of acetic acid for 3 hours. After finishing the reaction the solvent was distilled off under reduced pressure to obtain the objected 2-{2-methyl-4-[5-oxo-4-(4-trifluoromethylphenyl)-4,5-dihydrotetrazol-l-yhnethyl]phenyl}isoindol-l,3-dione [3.0g, ]H NMR (DMSO-do, ppm); 2.1 (3H, s), 5.2 (2H, s), 7.3-8.2 (HH,"m)].
Synthesis Example 13 (Starting Materjal Synthesis)
(Figure Removed)
l-(3-Methyl-4-nitrobenzyl)-3-(4-trifluoromethylphenyl)urea (1.0 g) was dissolved in 20 ml of dichloromethane, to which 5 ml of dichloromethane solution of oxalyl chloride (0.49 g) was added at room temperature, and the mixture was stirred for 8 hours. After the solvent was distilled off under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain the objected !-(3-me1hyl-4-ni1robenzyl)-3-(4-irifluoromemylphenyl)imidazolidin-2,4)5-trione [l.lg, 'H NMR (CDC13, ppm); 2.6 (3H, s), 4.9 (2H, s), 7.3-8.0 (7H, m)].
Synthesis Example 14 (Starting Material Synthesis)

Methyl solutiou (5 ml) of 3-methyl-4-nitrobenzaldehyde (0.9 g) was added to a methanol suspen-sion (5 ml) of glycrne ethyl ester acetate (1.1 g) and sodium cyanotrihydroborate (0.53 g) at 0°C. After stirring the mixture at room temperatuure for 10 hours, 2N hydrochloric acid (10 ml) and ethyl acetate (10 ml) were added thereto. After removing the organic layer, IN aqueous solution of sodium hydroxide .(30 ml) was,added to the aqueous layer and extracted with ethyl acetate. After washing the organic layer with a saturated aqueous solution of sodium chloride (20 ml), it was dried with anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain the objected ethyl (3-metbyl-4-nitrobenzylamino)acetate [0.9 g, 'H NMR (CDC13, ppm) ; 1.2 (3H, t), 2.6 (3H, s), 3.4 (2H, s), 3.9 (2H3 s), 4.2 (2H, q), 4.8 (2H, s), 7.2-8.1 (3H, m)].

Synthesis Example 15 (Starting Material Synthesis)

(Figure Removed)4-(trifluoromethyl)phenylisocyanate (0.83 g) was addedto a diethyl ether solution (50 ml) of ethyl (3-methyl-4-nitrobenzylamino)acetate (0.9 g) and the mixture was stirred vigorously at room tempe-rature for 7 hours. By filtering the crystals a erude product ethyl [l-(3-methyl-4-nitrobenzyl)-3-(4-trifluoromethylphenyl)ureido]acetate (0.8 g) was obtained and used in the next reaction without purification.
Synthesis Example 16 (Starting Material Synthesis)
(Figure Removed)Acetic acid solution (lO ml) of ethyl [l-(3-methyl-4-nitrobenzyl)-3-(4-trifluoromethylphenyl)-ureidojacetate (0.5 g) and concentrated hydrochloric acid (3 ml) was refluxed for 5 hours. After adding water (50 ml) the mixture was extracted with ethyl acetate. After washing the organic layer with water and a saturated aqueous solution of sodium chloride, it was dried with anhydrous magnesium sulfate. After the solvent was distüled off under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain the objected l-(3-methyl-4-nitrobenzyl)-3-(4-trifluoromethylphenyl)imidazolidin-2,4-dione [0.3 g, 'H NMR (CDC13, ppm) ; 2.7 (3H, s), 4.0 (2H, s), 4.8 (2H, s), 7.2-8.2 (7H, m)].
Synthesis Example 17 (Starting Material Synthesis)
(Figure Removed)4-Chloromethyl-2-methyl-l-mtrobenzene (1.9 g), aminoacetaldehyde dimethyl acetal (6.3 g) and potassium carbonate (6.2 g) were mixed in acetonitrile (200 ml) and the mixture was refluxed for 20 hours. After adding water the mixture was extracted with ethyl acetate. After washing the organic layer with a saturated aqueous solution of sodium clüoiide, it was dried with anhydrous magnesium sulfate. After the solvent was distüled off under reduced pressure., the obtained residue was purified by silica gel column chromatography to obtain the objected (2J2-dimethoxyeÜiyl)-3-(methyl-4-

ni1robenzyl)amine [2.5g, 'H NMR (CDC13, ppm) ; 2.6 (3H, s), 2.8 (2H, d), 3.5 (6H, s), 3.9 (2H, s), 4.6 (IH, m), 7.2-8.l (4H, m)].
Synthesis Example 18 (Starting Materjal Synthesis)

(Figure Removed) (232-Dimemoxye%l)-3-(methyl-4-nitrobenzyl)arnine (1.2 g) was dissolved in ether (50 ml), to which 4-(trifluoromethyl)phenyl- isocyanate (l .3 g) was added at room temperature, and the mixture was stirred vigorously for l hours. After finishing the reaction, water was added to tiie mixture and it was extracted with ethyl acetate. After drying the organic layer with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain a erude product l-(2,2-dimethoxyethyl)-l-(3-methyl-4-nitrobenzyl)-3-(4-(trifluoromethyIphenyL)urea (1.8 g), which was used in the next reaction without purification.
Synthesis Example 19 (Starting Materjal Synthesis)
(Figure Removed)l-(2,2-Dimethoxyettiyl)-l-(3-me1iiyl-4-nitrobenzyl)-3-(4-(trifluorornethylphenyl)urea (1.8 g) was dissolved in THF (5 ml), to which 50 % aqueous solution of trifluoroacetic acid (20 ml), and the mixture was stirred at room temperature. After finishing the reaction and adding water, the mixture was extracted with ethyl acetate. After washing the organic layer with water and a saturated aqueous solution of sodium chloride, it was dried with anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain the objected l-(3-methyl-4-nitrobenzyl)-3-(4-(trifluoromethylphenyl)-l,3-dihydroimidazol-2-one [1.2 g, 'H NMR (CDC13, ppm) ; 2.6 (3H, s), 4.9 (2H, s), 6.4 (IH, d), 6.7 (IH, d), 7.2-8.1 (7H, m)].

Biological Test Example 1: Test against larva of Spodoptera litura
Preparation of test agent:
Solvent: Dimethylformamide 3 parts by weight
Emulsifier. Polyoxyethylene alkyl phenyl ether 1 part by weight
hi order to make an appropriate formulation of an active compound, 1 part by weight of the active compound was mixed with the above-mentioned amount of solvent containing the above-mentioned amount of emulsifier and the mixture was diluted with water to a prescribed concentration.
Test method:
Leaves of sweet potato were soaked in the test "agent diluted to a prescribed concentration with water, dried in the air and put in a dish of 9 cm diameter. 10 larvae of Spodoptera litwa at the third instar were placed on the leaves and kept in a room at the constant temperature of 25°C. After 2 and 4 days further leaves of sweet potato were added and after 7 days the number of dead larvae was counted and the rate of death was calculated.
In this test the results of 2 dishes at 1 section were averaged.
Test results:
As specific examples the compounds of the compound no. 2-7, 2-35,2-67, 2-71, 2-72, 2-96, 2-140, 2-141, 2-142, 2-147, 2-173, 2-176, 2-181, 2-182, 2-270, 2-2S3, 2-293, 2-323, 2-333 and 2-337 showed 100% of rate of death at 20 ppm concentration of effective component.
Biological Test Example 2: Test against larva of Cnaphalocrocis medinalis Guenee
■ Test method:
Rice seedlings (cultivar: Tamanishiki) of 4-5 leaf stage, planted in a vinyl pot (9 cm diameter) were sprayed with the diluted aqueous solution of the prescribed concentration of the active compound prepared in the same manner as in the above mentioned Biological Test Example 1. After drying, top 1/3 part of the leaves of the plants was cut and put into a Petri-dish (9 cm diameter), in which a piece of filter paper (9 cm diameter) was laid and moistened. Five larvae of Cnaphalocrocis medinalis at the second instar were released in the Petri-dish and the dish was placed in a room at the constant temperature of 25°C. After 2 and 4 days, another 1/3 part of the plant leaves was cut and added to the dish. After seven days, the number of dead larvae was counted and the rate of death was calculated. In this test the results of 2 dishes at 1 treatment were averaged. Test results:

As specific examples the compounds of the compound no. 2-12, 2-17, 2-50, 2-54, 2-140, 2-141, 2-154, 2-172, 2-173,2-234,2-248,2-253, 2-256,2-310, 2-333, 2-337, 4-8,4-15 and 4-16 showed 100% of rate of death at 20 ppm concentration of effective component
Formulation Example l (Granule)
To a mixture of 10 parts of the compound of the present invention (No. 2-7), 30 parts of bentonite (montmorillonite), 58 parts of taie and 2 parts of ligninsulfonate salt, 25 parts of water are added, well kneaded, made into granules of 10-40 mesh by an extrusion granulator and dried at 40-50°C to obtain granules.
Fomiulation Example 2 (Granules)
95 Parts of clay mineral partides häving partide diameter distribution in the range of 0.2-2 mm are
put in a rotary mixer. While rotating it, 5 parts of the compound of the present invention (No. 2-173)
are sprayed together with a liquid diluent, wetted uniformly and dried at 40-50°C to obtain granules.
Formulation Example 3 (Emulsifiable Concentrate)
30 Parts of the compound of the present invention (No. 2-140), 55 parts of xylene, 8 parts of polyoxy-ethylene alkyl phenyl ether and 7 parts of calcium alkylbenzenesulfonate are mixed and stirred to obtain an emulsifiable concentrate.
Formulation Example4 (Wettable Powder)
15 Parts of the compound of the present rnvention (No. 2-333), 80 parts of a mixture of white carbon (hydrous amorphous silicon oxide fine powders) and powder clay (1:5), 2 parts of sodium alkylbenzenesulfonate and 3 parts of sodium alkyhiaphthalenesulfonate-formalin-condensate are crushed and mixed to make a wettable powder.
Formulation Example 5 (Water Dispersible Granule)
20 Parts of the compound of the present invention (No. 2-337), 30 parts of sodium ligninsulfonate, 15 parts of bentonite and 35 parts of calcined diatornaceous earth powder are well mixed, added with water, extruded with 0.3mm screen and dried to obtain water dispersible granules.

WE CLAIM:
1. Phthalamide derivatives represented by the formula
(Formula Removed)
wherein
X represents hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, nitro,
cyano, C1-C6-alkyl-sulfonyloxy, C1-C6-haloalkylsulfonyloxy,
phenylsulfonyloxy, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkylsulfinyl-C1-
C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C6-
alkylsulfonylamino, bis(C1-C6-alkylsulfonyl)amino or C1-C6-alkoxycarbonyl,
n represents 1, 2, 3 or 4,
Y represents hydrogen, halogen, C1-C6alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, or cyano,
m represents 1, 2, 3 or 4,
R1 represents C1-C6-alkyl or C1-C6-alkyl which is mono- or poly-
substituted by substituents selected from the group consisting of
cyano, nitro, C1-C6-alkylaminosulfonyl, N,N-di(C1-C6-
alkyl)aminosulfonyl, C1-C6-alkylsulfonylamino, N-C1-C6-alkylsulfonyl-
N-C1-C6-alkylamino, C1-C6-alkyl-carbonylamino, halo-C1-C6-alkyl, N-
C1-C6-alkyl-carbonyl-N-C1-C6-alkylamino, C1-C6-alkyl-
thiocarbonylamino, N-C1-C6-alkylthiocarbonyl-N-C1- C6-alkylamino, C1-C6-alkoxyimino-C1-C6-alkyl, C1-C6-alkyl-aminocarbonyl, N,N-di(C1-C6-alkyl)-aminocarbonyl, C1-C6-alkyl-aminothiocarbonyl, N,N-di(C1-C6-alkyl)-aminothiocarbonyl, C1-C6-alkoxy-carbonylamino, C1-C6-
alkoxy-carbonyl-C1-C6-alkylamino, C1-C6-alkylamino-carbonyloxy,
N,N-di(C1-C6-alkyl)amino-carbonyloxy, C1-C6-alkoxy-
thiocarbonylamino, C1-C6-alkoxy-thiocarbonyl-C1-C6-alkylamino, C1-
C6-alkylamino-thiocarbonyloxy, N,N-di(C1-C6-alkyl)-amino-
thiocarbonyloxy, C1-C6-alkylthio-carbonylamino, C1-C6-alkylthio-
carbonyl-C1-C6-alkylamino, C1-C6- alkylamino-carbonylthio, N,N-
di(C1-C6-alkyl)amino-carbonylthio, C1-C6-alkylthio-thiocarbonylamino,
C1-C6-alkylthio-thiocarbonyl-C1-C6-alkylamino, C1-C6-alkylamino-
thiocarbonylthio, N,N-di(C1-C6-alkyl)amino-thiocarbonylthio, C3-C6-cycloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylthio-C1-C6-alkyl, Ci-C6-alkylsulfinyl-C1-C6-alkyl and C1-C6-alkylsulfonyl-C1-C6-alkyl, or C3-C8-cycloalkyl which may be substituted by substituents selected from the group consisting of C1-C4-alkyl, C1-C4-alkylthio or C1-C2-alkylthio-Ci-C2-alkyl,
R2 represents hydrogen or C1-C6-alkyl,
R3 represents hydrogen or C1-C6-alkyl,
A1 represents straight chain or branched chain C1-C6-alkylene,
r represents 1,
A2 represents straight chain or branched chain C1-C6-alkylen, C1-C6-haloalkylene C2-C8-alkenylene, C2-C8-haloalkenylene, C2-C8-alkynylene or C2-C8-haloalkynylene,
s represents 0,
Q represents a heterocyclic group selected from
(Formula Removed)
W1 represents halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloallkyl, C1-C6-haloalkoxy, C1-C6-haloalkylthio, C1-C6-haloalkylsulfinyl, C1-C6-haloalkylsulfonyl,
C3-C6-cycloalkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1 -C-6-alkylsulfonyl-C1 -C6-alkyl,
W3 represents hydrogen or has the same definition as the aforementioned W1,
E represents phenyl, biphenyl, naphthyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, thienyl, furyl or pyrrolyl, wherein said group may be optionally substituted with one or more substituents selected from the below-mentioned group of substituents W2 wherein said substituents may be identical or different,
W2 represents halogen, nitro, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkyl, C1-C6-haloalkoxy, C1-C6-haloalkylthio, C1-C6-haloalkylsulfinyl, C1-C6-haloalkylsulfonyl, C3-C6-cycloalkyl, C1-C6-alkylthio-C1 -C6-alkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl or C1-C6-alkylsulfonyl-C1-C6-alkyl, or represents C3-C5-alkylene, C3-C5-haloalkyylene, oxy-C2-C4-alkylene, oxy-C2-C4-haloalkylene, C2-C4-alkyleneoxy, C2-C4-haloalkylenoxy, C1-C3-alkylenedioxy or C1-C3-haloalkylenedioxy, in case that W2 are two adjacent substituents, and
P represents 0, 1, or 2.
2. Process for the preparation of the compounds of the formula (I) as claim in claim 1, comprising
(a) in case that R2 represents hydrogen, the step of reacting compounds of the formula (II)
(Formula Removed)
wherein R1, X and n have the same definition as mentioned in claim 1, with compounds of the formula (III)
(Formula Removed)
wherein R3, Y, m, A1, r, Q, A2, s and E have the same definition as mentioned in claim 1, in the presence of inert solvents.
3. Insecticidal compositions comprising at least one compound of the formula (I) as claimed in claim 1 in an amount of 0.1-95% by weight along with extenders.

Documents:

3942-DELNP-2005-Abstract-(19-01-2009).pdf

3942-delnp-2005-abstract.pdf

3942-DELNP-2005-Claims-(16-04-2009).pdf

3942-DELNP-2005-Claims-(19-01-2009).pdf

3942-delnp-2005-claims.pdf

3942-delnp-2005-complete specification (granted).pdf

3942-DELNP-2005-Correspondence-Others-(16-04-2009).pdf

3942-DELNP-2005-Correspondence-Others-(19-01-2009).pdf

3942-delnp-2005-correspondence-others.pdf

3942-DELNP-2005-Description (Complete)-(16-04-2009).pdf

3942-DELNP-2005-Description (Complete)-(19-01-2009).pdf

3942-delnp-2005-description (complete).pdf

3942-delnp-2005-form-1.pdf

3942-delnp-2005-form-18.pdf

3942-delnp-2005-form-2.pdf

3942-delnp-2005-form-3.pdf

3942-delnp-2005-form-5.pdf

3942-DELNP-2005-GPA-(19-01-2009).pdf

3942-delnp-2005-gpa.pdf

3942-DELNP-2005-Others-Document-(16-04-2009).pdf

3942-delnp-2005-pct-101.pdf

3942-delnp-2005-pct-210.pdf

3942-delnp-2005-pct-306.pdf

3942-delnp-2005-pct-409.pdf

3942-DELNP-2005-Petition-137-(19-01-2009).pdf

3942-DELNP-2005-Petition-138-(19-01-2009).pdf

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Patent Number

234226

Indian Patent Application Number

3942/DELNP/2005

PG Journal Number

31/2009

Publication Date

31-Jul-2009

Grant Date

12-May-2009

Date of Filing

02-Sep-2005

Name of Patentee

BAYER CROPSCIENCE AG

Applicant Address

ALFRED-NOBEL-STR.50, 40789 MONHEIM,GERMANY.

Inventors:

#	Inventor's Name	Inventor's Address
1	KATSUAKI WADA	5-12-15,NAKAKUKI, OYAMA-SHI,TOCHIGI 323-0806, JAPAN.
2	TAKUYA GOMIBUCHI	1-2-5,NINOMIYA,TSUKUBA-SHI,IBARAKI 305-0051,JAPAN.
3	YASUSHI YONETA	1-10-3, DOTE, KAZO-SHI, SAITAMA 347-0056,JAPAN.
4	YUICHI OTSU	1-5-7,EKIMINAMI-CHO, OYAMA-SHI, TOCHIGI 323-0822, JAPAN.
5	KATSUHIKO SHIBUYA	6-14-4,MIDORI, MINAMIKAWACHI-MACHI, KAWACHI-GUN,TOCHIGI 329-0433, JAPAN.
6	HANAKO MATSUO	908-1, YUKI, OAZA, YUKI-SHI, IBARAKI, 307-0001, JAPAN.
7	RUDIGER FISCHER	ZU DEN FUSSFALLEN 23, 50259 PULHEIM,GERMANY.

PCT International Classification Number

CO7D 257/04

PCT International Application Number

PCT/EP2004/002024

PCT International Filing date

2004-03-01

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	2003-70274	2003-03-14	Japan