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"Azinylimidazoazine And Azinylcarboxamides"

Abstract: Azinyl imidazoazines of formula (I), in which the symbols have the meanings (1) indicated in the description, are disclosed, as well as their salts and N oxides, processes for producing the same and new intermediate products. The use of the compounds of formula I and of the intermediate products for combating animal pests and undesirable micro-organisms is also disclosed.

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Patent Information

Application #
Filing Date
10 November 2006
Publication Number
35/2007
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
remfry-sagar@remfry.com
Parent Application

Applicants

BAYER CROPSCIENCE
ALFRED-NOBEL-STR 50,40789 MONHEIM,GERMANY

Inventors

1. HANS-GEORG SCHWARZ
HEINENBUSCH 19 E, 40764 LANGENFELD,GERMANY
2. JENS FRACKENPOHL
FURSTENBERGER STR 1, 40322 FRANKFURT,GERMANY
3. ACHIM HENSE
IM HAINDELL 85, 65843 SULZBACH,GERMANY
4. PETER LOSEL
LOHRSTR 90 A, 51371 LEVEDKUSEN,GERMANY
5. OLGA MALSAM
VOR DEM KLOSTERHOF 19, 51503 ROSRATH,GERMANY
6. KARL-HEINZ KUCK
PASTOR-LOH-STR, 30 A,40764 LANGENFELD,GERMANY
7. GERHARD KRAUTSRUNK
ROBERT-KOCH-STR 34 A, 40789 MONHEIM,GERMANY
8. CHRISTIAN ARNOLD
PASTOR-LOH-STR 42, 40764 LANGENFELD,GERMANY

Specification

Azinylimidazoazines and Azinylcarboxamides The invention concerns azinylimidazoazines and their derivatives, methods for their preparation and use as plant protection agents, in particular for the control of zoopests and plant diseases. The invention also concerns azinylcarboxamide intermediates for the preparation of anzinylimidazoazines and the use of these compounds as plant protection agents, in particular for the control of zoopests and plant diseases. Certain azinyltriazoles, azinyloxadiazoles and azinyloxadiazinones and their possible use as pest control agents, in particular as insecticides, are already known from the (patent) literature (cf. EP-A 185256, WO 01/14373, WO 02/12229). Further azinylcarboxamides with insecticidal activity are known from JP-07010841, JP-07025853 and WO-02/022583. Since the ecological and economic demands placed on modern plant protection agents are constantly increasing, particularly in respect of toxicity, selectivity, amount applied, residue formation and ease of manufacture, and since problems with, for example, resistance can occur, there is an ongoing demand to develop new plant protection agents which exhibit advantages over known agents, at least in subareas. It has now been found that new azinylimidazoazines of structure (I) and their salts and N oxides, Figure Removed where in structure (I) A1, A2, A3, A4 and A5 are the same or different and in each case stand for N (nitrogen) or the group C-R, whereby, however, the imidazoazine bicycle contains in every case 2 to 5 N atoms, and in no case are more than two N atoms next to each other, and whereby R in the group C-R in the individual cases can have in each case the same or different meanings in accordance with the following definition, R stands in each case for H (hydrogen), nitro, amino, cyano, halogen, or for in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino or dialkylamino, or optionally two neighbouring R groups together stand for alkanediy! or, together with the azine group to which they are connected, form a benzene ring, R.1 stands for (Ci-C4-)haloalkyl, and X stands for H (hydrogen), nitro, formyl, hydroximinomethyl (-CH=N-OH), aminoimino- methyl (-CHXN-NH2), amino, cyano, halogen, or in each case for optionally substituted COOH, aminocarbonyl (-CO-NH2), alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkoximinomethyl (-CH=N-O-Alkyl), alkylaminoiminomethyl (-CH=N-NH-alkyl), dialkylaminoiminomethyl, cycloalkylalkoxyiminomethyl, benzyloxyiminomethyl, akenyloxyiminomethyl, arylsulphonylaminoiminomethyl, alkylcarbonyloxyiminomethyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, aminocarbonyl, hydroxycarbonyl alkylaminocarbonyl, alkenylaminocarbonyl, alkynylaminocarbonyl, dialkylamino, dialkylaminocarbonyl, alkylcarbonylaminocarbonyl, N-alkyl-alkylcarbonylaminocarbonyl, alkoxycarbonylaminocarbonyl, N-alkyl-alkoxycarbonylaminocarbonyl, alkyl- aminocarbonylaminocarbonyl, N-alkyl-N-alkylaminocarbonylaminocarbonyl, alkenyl, alkenyloxy, alkenylamino, alkenyloximinomethyl, alkynyl, alkynyloxy, alkynylamino, cyctoalkyl, cycloalkyloxy, cycloalkylalkoximinomethyl, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylamino, aryl, aryloxy, arylthio, arylamino, arylaminoiminomethyl, arylalkyl, arylethynyl, arylalkoxy, arylalkylthio, atylalkylamino, arylalkylaminoirninomethyl, arylalkoxyiminomethyl, arylsulphonylaminoiminomethyl, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, heterocyclylalkyl, heterocyclylalkynyl, heterocyclylalkoxy, heterocyclylalkylthio or heterocyclylalkylamino. Preferred substituents or preferred ranges of the residues present in the formula shown above and listed below are defined in the following. A1, A2, A3, A4 and A5 are the same or different and stand in each case preferably for N (nitrogen) or the group C-R, whereby, however, the imidazoazine bicycle contains 2 to 5 nitrogen atoms and in no case are more than two N atoms next to each other and were R in the group C-R in the individual cases can in each case have the same or different meanings in accordance with the following definitions. R stands in each case for preferably H (hydrogen), nitro, amino, cyano, halogen, or for alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino or dialkylamino with in each case 1 to 6 carbon atoms in the alkyl group, in each case optionally substituted by cyano, halogen or Ci-C4-alkoxy, or optionally two neighbouring R groups together stand for alkanediyl with 3 to 5 carbon atoms, or optionally two neighbouring R groups, together with the azine group to which they are connected, form a benzene ring. R1 stands preferably for CF3, CH F2 or CF2C1. X stands preferably for H (hydrogen), hydroxycarbonyl (COOH), nitro, formyl, hydroximinomethyl (-CH=N-OH), aminoiminomethyl (-CH=N-NH2), amino, cyano, halogen, for alkyl with 1 to 6 carbon atoms, optionally substituted by cyano, hydroxy, halogen, CrC4-alkoxy, Ci-C4-alkylamino, di(CrC4-alkyl)-aminocarbonyloxy, CrC4- alkylcarbonyloxy, benzylarnino, dibenzylamino, pyrrolidinyl, piperidinyl (which is optionally substituted by CrC4-haloalkyl), morpholinyl (which is optionally substituted by CrC4-alkyl) piperazinyl, N-methylpiperazinyl or di(CrC4-alkyl)-amino, for aminocarbonyl optionally substituted by benzyloxycarbonyl or N,O-di(CrC4- alkyl)hydroxylaminocarbonyl, for alkylcarbonyl, alkoxy, alkoxycarbonyl, alkoximino- methyl (-CH=N-O-alkyl), alkylaminoiminomethyl (-CH=N-NH-alkyl), dialkylaminoimino- methyl, benzyloxyiminomethyl, C2-C5-alkenyloxyiminomethyl, phenylsulphonylaminoiminomethyl, alkylcarbonyloxyiminomethyl, alkylthio, alkyl- sulphinyl, alkylsulphonyl, alkylamino, alkylaminocarbonyl, dialkylamino, dialkylamino- carbonyl, alkylcarbonylaminocarbonyl, N-alkyl-alkylcarbonylaminocarbonyl, alkoxy- carbonylaminocarbonyl, N-alkyl-alkoxycarbonylaminocarbonyl, alkylaminocarbonylaminocarbonyl or N-alkyl-N-alkylaminocarbonylaminocarbonyl with in each case 1 to 6 carbon atoms in the alkyl groups, in each case optionally substituted by cyano, hydroxy, halogen, Ci-C4-alkoxy, Ci-C4-alkoxycarbonyl, benzyloxycarbonyl orN,O-dialkylhydroxylaminocarbonyl, for alkenyl, alkenyloxy, alkenylamino, alkenylaminocarbonyl, alkenyloximinomethyl, alkynyl, alkynyloxy, alkynylaminocarbonyl or alkynylamino with in each case 2 to 8 carbon atoms in the alkenyl or alkynyl groups, optionally substituted by cyano, hydroxy, CpCe-alkoxy, phenyl (which itself is optionally substituted by nitro, amino, hydroxy, cyano, carbamoyl, thiocarbamoyl, halogen, Ci-C4-alkyl, C1-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulphinyl, d-Q-haloalkylsulphinyl, Ci-C4-alkylsulphonyl, Ci-C4-haloalkylsulphonyl, Ci-C4-alkylamino, di(Ci-C4-alkyl)-amino, di(Ci-C4-alkyl)aminocarbonyl, di(Ci-C4-alkyl)aminosulphonyl), phenoxy, heterocyclyl (with in each case up to 8 carbon atoms and at least one heteroatom from the series N (nitrogen), O (oxygen), S (sulphur) and optionally with a group CO, CS, SO or SO2 as component of the heterocycle, which itself is optionally substituted by halogen or CrC4-alkyl), CrC4-alkoxycarbonyl, benzyloxycarbonyl, N,O-di(Ci-C4-alkyl)aminocarbonyl, trialkylsilyl or halogen, for cycloalkyl, cycloalkyloxy, cycloalkylalkoximinomethyl, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy or cycloalkylalkylamino with in each case 3 to 6 carbon atoms in the cycloalky group and optionally with 1 to 4 carbon atoms in the alkyl parts, in each case optionally substituted by cyano, halogen, CrC4-alkyl or CrC4-haloalkyl, for aryl, aryloxy, arylthio, arylamino, arylaminoiminomethyl, arylalkyl, arylethynyl, aryl-alkoxy, arylalkylthio, arylalkylamino, arylalkylaminoiminomethyl, arylalkoxyiminomethyl or arylsulphonylaminoiminomethyl with in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, in each case optionally substituted by nitro, amino, hydroxy, cyano, carbamoyl, thiocarbamoyl, halogen, CrC4- alkyl, Ci-C4-haloalkyl, CrC4-alkoxy, C,-C4-haloalkoxy, CrC4-alkylthio, C,-C4-haloalkyI- thio, CrC4-alkylsulphinyl, CrC4-halogenalkylsulphinyl, Ci-C4-alkylsulphonyl, Ci-C4- haloalkylsulphonyl, CrC4-alkylamino, di(Ci-C4-alkyl)-amino, di(d-C4- alkyl)aminocarbonyl, di(Ci-C4-alkyl)-amino-sulphonyl, phenoxy or phenyl, or for heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, heterocyclylalkyl, heterocyclylalkynyl, heterocyclylalkoxy, heterocyclylalkylthio or heterocyclylalkylamino with in each case up to 8 carbon carbon atoms and at least one heteroaton from the series N (nitrogen), O (oxygen), S (sulphur) and optionally also a group CO, CS, SO or SOa as component of the heterocycle as well as optionally up to 4 carbon atoms in the alkyl or alkynyl part, optionally substituted by in each case nitro, amino, hydroxy, cyano, carbamoyl, thiocarbamoyl, halogen, Ci-C4-alkyl, CrC4-haloalkyl, CrC4-alkoxy, CrC4-halooalkoxy, C,-C4-alkylthio, C,-C4-alkylthio-CrC4-alkyl, CrC4-haloalkylthio, CrC4-alkylsulphinyl, Ci-C4-halogenalkylsulphinyl, CrC4-alkylsulphonyl, Ci-C4-halogenalkyl-sulphonyl, CrC4-alkylamino, di(Ci-C4-alkyl)amino, di(Ci-C4-alkyl)aminocarbonyl, di(Ci-C4-alkyl)aminosulphonyl, benzyl, thienylsulphonylmethyl, piperidinomethyl or phenyl, or for 2,4-dioxaspiro[5,5]undec-8-en-3-yl or 2,4-dioxaspiro[5.5]undecan-3-yl A1, A2, A3, A4 and A5 are the same or different and in each case stand more preferably for N (nitrogen) or the group C-R, whereby the imidazoazine bicycle contains 2 to 4 N atoms and whereby R in the group C-R in the individual case can have in each case the same or different meanings in accordance with the following definition. R stands more preferably for H (hydrogen), nitro, amino, cyano, fluorine, chlorine, bromine, iodine or for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, in each case optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, or optionally two neighbouring R groups together stand for propane-1,3-diyl, butane-1,3-diyl, butane-1,4-diyl, pentane-1,3-diyl, pentane-l,4-diyl or pentane-l,5-diyl, or optionally two neighbouring R groups, together with the azine group to which they are connected, form a benzene ring. R! stands more preferably for CF3. X stands more preferably for H (hydrogen), hydroxycarbonyl (COOH), for aminocarbonyl optionally substituted by benzyloxycarbonyl, N.O-dimethylhydroxylaminocarbonyl, N,O- diethylhydroxylaminocarbonyl, N-methyl-O-ethylhydroxylaminocarbonyl or N-ethyl-O- methylhydroxylaminocarbonyl, for nitro, formyl, hydroximinomethyl (-CHMN-OH), aminoiminomethyl (-CH=N-NH2), amino, cyano, fluorine, chlorine, bromine, iodine, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s-, t- or neo-pentyl in each case optionally substituted by cyano, hydroxy, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, benzyloxy, methylamino, ethylamino, n- or i-propyl- amino, n-, i-, s- or t-burylamino, dimethylaminocarbonyloxy, diethylaminocarbonyloxy, methylcarbonyloxy, ethylcarbonyloxy, benzylamino, dibenzylamino, dimethylamino, diethylamino or dipropylamino, for methyl substituted by the group NR'R" (whereby R'R" together with the nitrogen atom stands for pyrrolidine, piperidine, 4- trifluoromethylpiperidine, 3-trifluoromethylpiperidine, fluoromethylpiperidine, morpholine, dimethylmorpholine, piperazine or N-methylpiperazine), for acetyl, propionyl, n- or i-buryroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methoximinomethyl, ethoximinomethyl, methylaminoiminomethyl, ethylarmnoiminomethyl, n- or i-propyl- aminoiminomethyl, dimethylaminoiminomethyl, cyclohexylmethoxyiminomethyl, cycloentylmethoxyiminomethyl, cyclopropylmethoxyiminomethyl, benzyloxyiminomethyl, chlorobenzyloxyiminomethyl, ethylcarbonyloxyiminomethyl, methylcarbonyloxyiminomethyl, allyloxyiminomethyl, phenylsulphonylaminoiminomethyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t- butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethyl- sulphonyl, n~ or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, diethylamino, di-n-propylamino, di-i-propylamino, dimethylamino- carbonyl, diethylaminocarbonyl, acetylaminocarbonyl, propionylaminocarbonyl, n- or i- butyroylaminocarbonyl, N-methyl-acetylaminocarbonyl, N-methyl-propionyl- aminocarbonyl, methoxycarbonylaminocarbonyl, ethoxycarbonylaminocarbonyl, n- or i- propoxycarbonylaminocarbonyl, N-methyl-methoxycarbonylammocarbonyl, N- methylethoxycarbonylaminocarbonyl, methylaminocarbonylaminocarbonyl, ethylammocarbonylaminocarbonyl, n- or i-propylamtno-carbonylaminocarbonyl, N-methylmethylaminocarbonylaminocarbonyl, N-methyl-ethylaminocarbonylamino, N,O-dimethylhydroxylaminocarbonyl, N,O-diethylhydroxylaminocarbonyl, N-methyl-O-ethylhydroxylaminocarbonyl, N-ethyl-O-methylhydroxylaminocarbonyl, in each case optionally substituted by cyano, hydroxy, fluorine, chlorine, bromine, methoxy, ethoxy, n-or i-propoxy, n-, i-, s- or t-butoxy, for ethenyl, propenyl, butenyl, pentenyl, hexenyl, propenyloxy, butenyloxy, pentenyloxy, propenylamino, butenylamino, pentenylamino, allyloximinomethyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, propynyloxy, butynyloxy, pentynyloxy, propynylaminocarbonyl, butynylaminocarbonyl or pentynyl- aminocarbonyl, in each case optionally substituted by cyano, hydroxy, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, phenyl (which itself is optionally substituted by Ci-C4- alkyl, CpQ-alkoxy, halogen, Ci-Q haloalkyl), phenoxy, heterocyclyl (selected from furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, pyrazolyl, pyrazolinyl, oxazolyl, oxazolinyl, isoxazolyl, isoxazolinyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrrolidinyl, morpholinyl, piperazinyl or pyrimidinyl, which are optionally substituted by halogen or Ci-C4-alkyl), trialkylsilyl, ethoxycarbonyl, methoxycarbonyl, fluorine, chlorine or bromine, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclo- propyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino, cyclobutyl- amino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethoximinomethyl, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexyl- methylamino optionally substituted by cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl or trichloromethyl, for phenyl, naphthyl, phenoxy, naphthyloxy, phenylthio, naphthylthio, phenylamino, naphthylamino, phenylaminoiminomethyl, benzyl, phenylethyl, phenylpropyl, phenylethynyl, phenyl- methoxy, phenylethoxy, phenylpropoxy, phenylmethylthio, phenylmethylamino, phenyl- ethylamino, phenylmethylaminoiminomethyl, phenylmethoxyiminomethyl or phenylsulphonylaminoiminomethyl, in each case optionally substituted by nitro, amino, hydroxy, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, trifluoroethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, trifluoromethylsulphinyl, methylsulphonyl, ethylsulphonyl, trifluoromethylsulphonyl, methylamino, ethylamino, n-or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethylamino-carbonyl, diethylaminocarbonyl, dimethylaminosulphonyl, diethylaminosulphonyl, phenoxy or phenyl, for heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, heterocyclylmethyl, heterocyclylethynyl, heterocyclylmethoxy, heterocyclylmethylthio or heterocyclylmethylamino, in each case optionally substituted by nitro, amino, hydroxy, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, trifluoroethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylthiomethyl, ethylthiomethyl, difluoromethylthio, trifluoromethyjthio, chlorodifluoromethylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, trifluoromethylsulphinyl, methylsulphonyl, ethylsulphonyl, trifluoromethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminosulphonyl, diethylaminosulphonyl, thienylsulphonylmethyl, piperidinomethyl, benzyl or phenyl, whereby heterocyclyl in each case stands especially for furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, pyrazolyl, pyrazolinyl, oxazolyl, oxazolinyl, isoxazolyl, isoxazolinyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, dioxolanyl, dioxanyl, pyridinyl, piperidinyl, morpholinyl, pyrimidinyl or piperazinyl or for 2,4-dioxaspiro[5.5]undec-8-en-3-yl, 2,4-dioxaspiro[5.5]undecan-3-yl. A1, A2, A3, A4 and A5 are the same or different and in each case stand most preferably for N (nitrogen) or the group C-R, wherein, however, the imidazoazine bicycle contains 2 or 3 N atoms and R in the group C-R in the individual cases can have each time the same or different meanings in accordance with the following definition. R stands in each case most preferably for H (hydrogen), nitro, amino, cyano, fluorine, chlorine, bromine, iodine, or for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, in each case optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, or optionally two neighbouring R groups together stand for propane-1,3-diyl, butane-1,3-diyl, butane-1,4-diyl, pentane-1,3-diyl, pentane-l,4-diyl or pentane-l,5-diyl, or optionally two neighbouring R groups ,together with the azine group to which they are connected, form a benzene ring. R1 stands most preferably for CF3- X stands most preferably for H (hydrogen), hydroxycarbonyl (COOH), for aminocarbonyl optionally substituted by benzyloxycarbonyl, N,O-dimethylhydroxylaminocarbonyl, N,O-diethylhydroxylaminocarbonyl, N-methyl-O-ethylhydroxylaminocarbonyl or N-ethyl-O- methylhydroxylaminocarbonyl, for nitro, formyl, hydroxyiminomethyl, aminoimino- methyl, amino, cyano, fluorine, chlorine, bromine, iodine, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, in each case optionally substituted by cyano, hydroxy, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylcarbonyloxy, ethylcarbonyloxy, dimethylaminocarbonyloxy, methylamino, ethylamino, dimethylamino, diethylamino, dipropylamino, benzylamino or dibenzylamino, for methyl substituted by the group-NR'R" (where R'R" together with the nitrogen stands for pyrrolidine, piperidine, 4-trifluoromethylpiperidine, 3-trifluoromethylpiperidine, fluoromethylpiperidine, morpholine, dimethylmorpholine, piperazine or N-methylpiperazine), acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methoximinomethyl, ethoximinomethyl, cyclopropylmethoxyiminomethyl, benzyloxyiminomethyl, chlorbenzyloxyiminomethyl, methylcarbonyloxyiminomethyl, allyloxyiminomethyl, phenylsulphonylaminoiminomethyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethyl-sulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s-or t-butylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, diethylamino, dimethylaminocarbonyl, acetylaminocarbonyl, propionyl-aminocarbonyl, n- or i-butyroylaminocarbonyl, N-methyl-acetylaminocarbonyl, N-methylpropionylaminocarbonyl, methoxycarbonylaminocarbonyl, ethoxy carbonyl-arninocarbonyl, n- or i-propoxycarbonylaminocarbonyl, N-methy I-methoxycarbonylaminocarbonyl, N-methylethoxycarbonylaminocarbonyl, in each case optionally substituted by cyano, hydroxy, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylcarbonyloxy, ethylcarbonyloxy, dimethylaminocarbonyloxy, methylamino, ethylamino, dimethylamino, diethylamino, dipropylamino, benzylamino or dibenzylamino, for methylaminocarbonylaminocarbonyl, ethylaminocarbonylaminocarbonyl, n- or i-propylaminocarbonylaminocarbonyl, N-methylmethylaminocarbonylaminocarbonyl, N-methylethylaminocarbonylaminocarbonyl, N,O-dimethylhydroxylaminocarbonyl, N,O-diethylhydroxylaminocarbonyl, N-methyl-O-ethylhydroxylaminocarbonyl, N-ethyl-O-methylhydroxylaminocarbonyl), in each case optionally substituted by cyano, for ethenyl, propenyl, butenyl, pentenyl, propenyloxy, butenyloxy, pentenyloxy, propenylamino, butenylamino, pentenylamino, allyloximinomethyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, propynyloxy, butynyloxy, pentynyloxy, propynylaminocarbonyl, butynylaminocarbonyl or pentynylaminocarbonyl in each case optionally substituted by cyano, hydroxy, methoxy, ethoxy, n- or i-propoxy, pyridyl (which is optionally substituted by halogen), thienyl, thiazolyl (which itself is optionally substituted by methyl or ethyl), trialkylsilyl, phenyl (which itself is optionally substituted by methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, bromine, iodine, or trifluoromethyl), phenoxy, methoxycarbonyl, ethoxycarbonyl, fluorine, chlorine or bromine, for cyclopropyl, cyclo-pentyl, cyclohexyl, cyclopropyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclopentylmethyl, cyclohexyl-methyl, cyclopropylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropyl-methylamino, cyclopentylmethylamino or cyclohexylmethylamino, in each case optionally substituted by cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl or trifluoromethyl, for dioxolan-2-yl, l,3-dioxan-2-yl, oxazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, phenyl, phenoxy, phenylthio, phenylamino, benzyl, phenylethyl, phenyl-ethynyl, phenylmethoxy, phenylethoxy, phenylmethylthio, phenylmethylamino or phenyl-ethylamino, in each case optionally substituted by nitro, amino, hydroxy, cyano, carbamoyl, thio-carbamoyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, trichloromethyl, fluorodichloromethyl, chloro-difluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, tri-fluoroethoxy, methylthio, ethylthio, n- or i-propylthio, methylthiomethyl, difluoromethyl-thio, trifluoromethylthio, chlorodifluoromethylthio, methylsulphinyl, ethylsulphinyl, tri-fluoromethylsulphinyl, methylsulphonyl, ethylsulphonyl, trifluoromethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, dimethylaminocarbonyl, dimethylaminosulphonyl, phenoxy, thienylsulphonylmethyl, piperidinomethyl, benzyl or phenyl, or for 2,4-dioxaspiro[5.5]undec-8-en-3-yl, 2,4-dioxaspiro[5.5]undecan-3-yl or phenylethylamino. Preferred are compounds of structure (I) in which the group R1 is in the ortho or para position relative to the nitrogen of the pyridine ring, more preferably in the para position. A most particularly preferred group are compounds of the structure (IA) Figure Removed whereby in the structure (IA) R and X have the aforementioned meanings and preferences or R which may be the same or different, and in each case stands most preferably for H (hydrogen), nitro, amino, cyano, fluorine, chlorine, bromine, iodine, or for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethyl-amino, n- or i-propylamino, dimethylamino or diethylamino, in each case optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, or in each case two neighbouring R groups together optionally stand for propane-l,3-diyl, butane-1,3-diyl, butane- 1,4-diyl, pentane-l,3-diyl, pentane-l,4-diyl or pentane-l,5-diyl, or in each case optionally two neighbouring R groups, together with the neighbouring azine group to which they are connected, form a benzene ring, where in all cases a maximum two R groups are different to H (hydrogen), and stands most preferably for H (hydrogen), nitro, formyl, hydroximinomethyl, amino, cyano, fluorine, chlorine, bromine, iodine, for methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methoximinomethyl, ethoximinomethyl, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, diethylamino, dimethylaminocarbonyl, acetyl-amino, propionylamino, n- or i-butyroylamino, N-methylacetylamino, N-methylpropionyl-amino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, N-methylmethoxycarbonylamino, N-methylethoxycarbonylamino, methylaminocarbonyl-arnino, ethylaminocarbonylamino, n- or i-propylamino-carbonylamino, N-methylmethylaminocarbonylamino, N-methyl-ethylaminocarbonylamino, in each case optionally cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, for ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino or butynylamino, in each case optionally substituted by cyano, fluorine, chlorine or bromine, for cyclopropyl, cyclo-pentyl, cyclohexyl, cyclopropyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclopentylmethyl, cyclohexyl-methyl, cyclopropylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropyl-methylamino, cyclopentylmethylamino or cyclohexylmethylamino, in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl or trifluoromethyl, for phenyl, phenoxy, phenylthio, phenylamino, benzyl, phenylethyl, phenyl-ethynyl, phenylmethoxy, phenylethoxy, phenylmethylthio, phenylmethylamino, phenyl-ethylamino or phenylethylamino, in each case optionally substituted by nitro, amino, hydroxy, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, trichloromethyl, fluorodichloro-methyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, tri-fluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, di-chloroethoxy, trifluoroethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methylsulphinyl, ethylsulphinyl, trifluoromethylsulphtnyl, methylsulphonyl, ethylsulphonyl, trifluoromethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, dimethylaminocarbonyl, dimethylaminosulphonyl or phenyl. A further most preferred group are the compounds of structure (IB), Figure Removed whereby in the structure (IB) R and X have the aforementioned meanings and preferences or R which may be the same or different, stands most preferably for H (hydrogen), nitro, amino, cyano, fluorine, chlorine, bromine, iodine or for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino in each case optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, or in each case two neighbouring R groups optionally stand for propane-1,3-diyl, butane-l,3-diyl, butane-1,4-diyl, pentane-l,3-diyl, pentane-l,4-diyl or pentane-l,5-diyl, or optionally in each case two neighbouring R groups, together with the azine group to which they are connected, form a benzene ring, whereby in all cases a maximum of two R groups are different from H (hydrogen), and X stands most preferably for H (hydrogen), nitro, formyl, hydroximinomethyl, amino, cyano, fluorine, chlorine, bromine, iodine, for methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methoximinomethyl, ethoximinomethyl, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, diethylamino, dimethylaminocarbonyl, acetyl-amino, propionylamino, n- or i-butyroylamino, N-methylacetylamino, N-methylpropionyl-amino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, N-methylmethoxycarbonylam ino, N-methylethoxycarbonylamino, methylaminocarbonyl- amino, methylaminocarbonylamino, n- or i-propylaminocarbonylamino, N-methylmethylaminocarbonylamino, N-methylethylaminocarbonylamino, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, for ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino or butynylamino, in each case optionally substituted by cyano, fluorine, chlorine or bromine, for cyclopropyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropyl-amino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclopentylmethyl, cyclohexylrnethyl, cyclopropylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl or trifluoromethyl, for phenyl, phenoxy, phenylthio, phenylamino, benzyl, phenyl-ethyl, phenylethynyl, phenylmethoxy, phenylethoxy, phenylmethylthio, phenylmethyl-amino, phenylethylamino or phenylethylamino in each case optionally substituted by nitro, amino, hydroxy, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, trichloromethyl, fiuorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, trifluoroethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methylsulphinyl, ethylsulphinyl, trifluoromethylsulphinyl, methylsulphonyl, ethylsulphonyl, trifluoromethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, dimethylaminocarbonyl, dimethylaminosulphonyl or phenyl. Particularly emphasised are also compounds with the following preferred residue combinations: A1, A2, A', A4 and A5 are the same or different and in each case stand preferably for N (nitrogen) or the group C-R, whereby, however, the imidazoazine bicycle contains 2 to 5 N atoms and in no case are more than two N atoms next to each other, and R in the group C-R in the individual cases can have in each case the same or different meanings in accordance with the following definitions. R stands in each case preferably for H (hydrogen), nitro, amino, cyano, halogen, or for alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino or dialkylamino with in each case 1 to 6 carbon atoms in the alkyl groups and in each case optionally substituted by cyano, halogen or CrC4-alkoxy, or optionally two neighbouring R groups together stand for alkanediyl with 3 to 5 carbon atoms, or optionally two neighbouring R groups, together with the azine group to which they are connected, form a benzene ring. R1 stands preferably for CF3, CH ?2 or CF2C1. X staands preferably for H (hydrogen), nitro, formyl, hydroximinomethyl (-CH=N-OH), aminoiminomethyl (-CH=N-NH2), amino, cyano, NCO (isocyanato), NCS (isothio-cyanato), halogen, for alkyl with 1 to 6 carbon atoms, optionally substituted by cyano, hydroxy, halogen, Ci-C4-alkoxy, Ci-C4-alkylamino or di(C|-C4-alkyl)-amino, for alkyl-carbonyl, alkoxy, alkoxycarbonyl, alkoximinomethyl (-CH=N-O-alkyl), alkylaminoimino-methyl (-CH=N-NH-alkyl), dialkylaminoiminomethyl, alkylthio, alkylsulphinyl, alkyl-sulphonyl, alkylamino, alkylaminocarbonyl, dialkylamino, dialkylaminocarbonyl, alkyl-carbonylamino, N-alkyl-alkylcarbonylamino, alkoxycarbonylamino, N-alkyl-alkoxy-carbonylamino, alkylaminocarbonylamino or N-alkyl-N-alkylaminocarbonylamino with each case 1 to 6 carbon atoms in the alkyl groups, in each case optionally substituted cyano, hydroxy, halogen or CrC4-alkoxy, for alkenyl, alkenyloxy, alkenylamino, alkenyl-oximinomethyl, alkynyl, alkynyloxy or alkynylamino with in each case 2 to 6 carbon atoms in the alkenyl or alkynyl groups, in each case optionally substituted by cyano, hydroxy, phenoxy or halogen, for cycloalkyl, cycloalkyloxy, cycloalkylalkoximinomethyl, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy or cycloalkylalkylamino with in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl parts, in each case optionally substituted by cyano, halogen, CrC4-alkyl or CrC4-haloalkyl, for aryl, aryloxy, arylthio, arylamino, arylaminoiminomethyl, arylalkyl, aryl-ethynyl, arylalkoxy, arylalkylthio, arylalkylamino, arylalkylaminoiminomethyl, arylalkoxy-iminomethyl or arylsulphonylaminoiminomethyl with in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, in each case substituted by nitro, amino, hydroxy, cyano, carbamoyl, thiocarbamoyl, halogen, Ci-C4-alkyl, Ct-C4-halogenalkyl, CrC4-alkoxy, CrC4-halogenalkoxy, Ci-C4-alkylthio, C^C^haloalkylthio, Ci-C4-alkylsulphinyl, Ci-C4-halogalkylsulphinyl, CrC4-alkylsulphonyl, Ci-C4-haloalkyl-sulphonyl, Ci-C4-alkylamino, di(Ci-C4-alkyl)-amino, di(Ci-C4-alkyl)aminocarbonyl, di(Cr C4-alkyl)aminosulphonyl or phenyl, or for heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, heterocyclylalkyl, heterocyclylalkynyl, heterocyclylalkoxy, heterocyclylalkylthio or heterocyclylalkylamino with in each case up to 8 carbon atoms and at least one heteroatom from the series N (nitrogen), O (oxygen), S (sulphur) and optionally also a group CO, CS, SO or SO2 as component of the heterocycle as well as up to 4 carbon atoms in the alkyl part or alkynyl part, in each case optionally substituted by nitro, amino, hydroxy, cyano, carbamoyl, thio-carbamoyl, halogen, Ci-C4-alkyl, CrC4-haloalkyl, CrC4-alkoxy, CrC4-haloalkoxy, CrC4-alkylthio, CrC4-haIoalkylthio, C,-C4-alkylsulphinyl, CrC4-halogenalkylsulphinyl, C]-C4-alkylsulphonyl, C|-C4-haloalkyl-sulphonyl, C|-C4-alkylamino, di(CrC4-alkyl)amino, di(Ci-C4-alkyl)amino-carbonyl, di(Cr C

Documents

Application Documents

# Name Date
1 6662-delnp-2006-form-18 (08-05-2008).pdf 2008-05-08
1 6662-DELNP-2006.pdf 2016-06-30
2 6662-delnp-2006-correspondence-others (08-05-2008).pdf 2008-05-08
2 6662-delnp-2006-abstract.pdf 2011-08-21
3 abstract.jpg 2011-08-21
3 6662-delnp-2006-claims.pdf 2011-08-21
4 6662-delnp-2006-pct-search report.pdf 2011-08-21
4 6662-delnp-2006-correspondence-others.pdf 2011-08-21
5 6662-delnp-2006-pct-304.pdf 2011-08-21
5 6662-delnp-2006-description (complete).pdf 2011-08-21
6 6662-delnp-2006-gpa.pdf 2011-08-21
6 6662-delnp-2006-form-1.pdf 2011-08-21
7 6662-delnp-2006-form-5.pdf 2011-08-21
7 6662-delnp-2006-form-2.pdf 2011-08-21
8 6662-delnp-2006-form-3.pdf 2011-08-21
9 6662-delnp-2006-form-5.pdf 2011-08-21
9 6662-delnp-2006-form-2.pdf 2011-08-21
10 6662-delnp-2006-form-1.pdf 2011-08-21
10 6662-delnp-2006-gpa.pdf 2011-08-21
11 6662-delnp-2006-pct-304.pdf 2011-08-21
11 6662-delnp-2006-description (complete).pdf 2011-08-21
12 6662-delnp-2006-pct-search report.pdf 2011-08-21
12 6662-delnp-2006-correspondence-others.pdf 2011-08-21
13 abstract.jpg 2011-08-21
13 6662-delnp-2006-claims.pdf 2011-08-21
14 6662-delnp-2006-correspondence-others (08-05-2008).pdf 2008-05-08
14 6662-delnp-2006-abstract.pdf 2011-08-21
15 6662-DELNP-2006.pdf 2016-06-30
15 6662-delnp-2006-form-18 (08-05-2008).pdf 2008-05-08