Use of Strobilurin Type Compounds for Combating Phytopathogenic Fungi Resistant to QO Inhibitors

Abstract

The present invention relates to the use of strobilurine type compounds of formula I and the N-oxides and the salts thereof for combating phytopathogenic fungi containing a mutation in the mitochondrial cytochrome b gene conferring resistance to Qo inhibitors, and to methods for combating such fungi. The invention also relates to novel compounds, processes for preparing these compounds, to compositions comprising at least one such compound, to plant health applications, and to seeds coated with at least one such compound.

1 . (canceled) 
     
     
         2 . A compound of formula (I) 
       
         
           
           
               
               
           
         
         wherein: 
         R 1 , R 2  independently of each other are selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl and C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, wherein the groups R 1  and R 2  are cis-oriented, and
 wherein the aliphatic moieties of R 1  and/or R 2  may carry 1, 2, 3 or up to the maximum number of identical or different groups R a  which independently of one another are selected from: 
 R a  is selected from the group consisting of CN, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl and C 1 -C 4 -haloalkoxy; 
 
         Y is a direct bond or a divalent group selected from the group consisting of —OCH 2 —, —CH 2 —, —CH 2 CH 2 —, —C(Z)═N—O—CH 2 —, —CHZ—C(Z)═N—O—CH 2 —, —O—N═C(Z)—C(Z)═N—O—CH 2 —, —C(═O)—C(Z)═N—O—CH 2 — and —C(═N—O—Z)—C(Z)═N—O—CH 2 —, where the bond depicted on the left side of the divalent group Y is attached to R 3 , and the bond depicted on the right side is attached to the carbon atom being substituted by R 2 , and
 Z, which may be the same or different to any other Z, is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; 
 
         R 3  is selected from pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, 1,2,4-triazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl or 1,2,4-thia¬diazolyl;
 wherein the cyclic groups R 3  may carry 1, 2, 3, 4 or up to the maximum possible number of identical or different groups R b  which independently of one another are selected from the group consisting of: 
 R b , which may be the same or different to any other R b , is selected from the group consisting of amino, halogen, hydroxyl, oxo, nitro, CN, carboxyl, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C1-C4-haloalkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 1 -C 6 -alkoxyimino-C 1 -C 4 -alkyl, C 2 -C 6 -alkenyloxyimino-C1-C4-alkyl, C 2 -C 6 -alkynyloxyimino-C 1 -C 4 -alkyl, C 1 -C 4 -alkylamino, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkylcarbonyloxy, phenyl, naphthyl and a 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocyclyl which, in addition to carbon atoms, contains one to four heteroatoms selected from the group consisting of N, O and S as ring members; and wherein the aforementioned phenyl and heterocyclyl groups R b  are attached via a direct bond, an oxygen or sulfur atom;
 and 
 two radicals R b  that are bound to adjacent ring member atoms of the cyclic group R 3  may form together with said ring member atoms a fused 5-, 6- or 7-membered saturated, partially unsaturated or aromatic cycle, which may be a carbocycle or heterocycle, wherein the ring member atoms of the fused heterocycle include besides carbon atoms 1, 2, 3 or 4 heteroatoms selected from the group consisting of N, O and S, and 
 where the aliphatic or cyclic groups R b  for their part may carry 1, 2, 3 or up to the maximum possible number of identical or different groups R c : 
 R c , which may be the same or different to any other R c , is selected from the group consisting of halogen, hydroxyl, nitro, CN, carboxyl, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 8 -alkynyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 6 -alkoxyimino-C 1 -C 4 -alkyl, C 2 -C 6 -alkenyloxyimino-C 1 -C 4 -alkyl, C 2 -C 6 -alkynyloxyimino-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxyimino-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxyimino-, C 2 -C 6 -alkenyloxyimino-, C 2 -C 6 -alkynyloxyimino-, C 2 -C 6 -haloalkenyloxyimino-, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, phenyl and a 5-membered saturated, partially unsaturated or aromatic heterocyclyl which, in addition to carbon atoms, contains one to three heteroatoms selected from the group consisting of N, O and S as ring members; wherein the aforementioned cyclic groups R c  are attached via a direct bond, an oxygen or sulfur atom and where the aliphatic or cyclic groups R c  for their part may carry 1, 2, 3 or up to the maximum possible number of identical or different groups R d : 
 R d , which may be the same or different to any other R d , is selected from the group consisting of halogen, C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl; 
 
 or 
 
         R 3  is —CR A ═N—O—R B , wherein
 R A  is selected from the group consisting of amino, hydroxyl, C 1 -C 4 -alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 1 -C 4 -alkoxyimino-C 1 -C 4 -alkyl, C 1 -C 4 -alkylamino, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkylcarbonyloxy, phenyl, phenyl-C 1 -C 4 -alkyl, naphthyl and a 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocyclyl which, in addition to carbon atoms, contains one to four heteroatoms from the group consisting of O, N and S as ring members; and wherein the aforementioned cyclic R A  are attached via a direct bond, an oxygen or sulfur atom; 
 R B  is selected from the group consisting of C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 4 -alkoxyimino-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, phenyl, phenyl-C 1 -C 4 -alkyl, naphthyl and a 3- to 10-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocyclyl which, in addition to carbon atoms, contains one to four heteroatoms from the group consisting of O, N and S as ring members;
 where the aliphatic or cyclic groups R A  and/or R B  for their part may carry 1, 2, 3 or up to the maximum possible number of identical or different groups R e : 
 R e , which may be the same or different to any other R e , is selected from the group consisting of halogen, hydroxyl, nitro, CN, carboxyl, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 8 -alkynyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
 
 
         R 4  is a monovalent group selected from formulae R4-1 to R4-7 
       
       
         
           
           
               
               
           
         
         
           wherein the jagged line defines the point of attachment, and where 
           X is a divalent group O or NH, 
           R 5  is selected from the group consisting of C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy and C 3 -C 6 -cycloalkyl, 
           R 6  is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; 
         
       
       and the N-oxides and the agriculturally acceptable salts thereof, except for (2E,3Z)-2-(ethylidene)-5-phenyl-3-pentenoic acid methyl ester (CAS-No. 681026-20-0). 
     
     
         3 . The compound of  claim 2 , wherein R 1  is selected from the group consisting of hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -chloroalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl and C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl. 
     
     
         4 . The compound of  claim 3 , wherein R 1  is methyl or ethyl. 
     
     
         5 . The compound of  claim 2 , wherein R 2  is hydrogen. 
     
     
         6 . The compound of  claim 2 , wherein Y is selected from the group consisting of —OCH 2 —, —CH 2 CH 2 —, —C(CH 3 )═N—O—CH 2 —, —O—N═C(CH 3 )—C(CH 3 )═N—O—CH 2 — and —C(═N—O—CH 3 )—C(CH 3 )═N—O—CH 2 —. 
     
     
         7 . The compound of  claim 1 , wherein R b  is phenyl, wherein said phenyl is optionally substituted by 1, 2, 3 or up to the maximum possible number of identical or different groups R c , which may be the same or different to any other R c , wherein R c  is selected from the group consisting of halogen, C 1 -C 4 -alkyl, C2-C4-alkenyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxyimino-C 1 -C 4 -alkyl, phenyl and a 5-membered saturated, partially unsaturated or aromatic heterocyclyl which, in addition to carbon atoms, contains one to three heteroatoms selected from the group consisting of N, O and S as ring members; and wherein the aforementioned heterocyclyl groups R c  are attached via a direct bond, an oxygen or sulfur atom and for their part may carry 1, 2, 3 or up to the maximum possible number of identical or different groups R d . 
     
     
         8 . The compound of  claim 2 , wherein R 4  is selected from the group consisting of —C(═NOCH 3 )—CONHCH 3 , —C(═NOCH 3 )—COOCH 3 , —C(═CHOCH 3 )COOCH 3 , —C(═CHOCH 3 )—CONHCH 3 , —N(OCH 3 )—COOCH 3 , —N(CH 3 )—COOCH 3  and —N(CH 2 CH 3 )—COOCH 3 . 
     
     
         9 . The compound of  claim 2 , wherein R 3  is 
       
         
           
           
               
               
           
         
       
       wherein # indicates the point of attachment to the linker moiety Y;
 wherein the phenyl may carry 1, 2, 3 or up to the maximum possible number of identical or different groups R c , which may be the same or different to any other R c , is halogen. 
 
     
     
         10 . An agrochemical composition comprising an auxiliary and at least one compound of formula I, as defined in  claim 2 , an N-oxide or an agriculturally acceptable salt thereof. 
     
     
         11 . The composition of  claim 10  comprising at least one further active substance. 
     
     
         12 . The composition of  claim 11 , wherein the further active substance is selected from the classes A) to O):
 A) Respiration inhibitors
 Inhibitors of complex III at Q o  site selected from azoxystrobin, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, fenaminstrobin, fenoxystrobin/flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, 2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic acid methyl ester and 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl-acetamide, pyribencarb, triclopyricarb/chlorodincarb, famoxadone, and fenamidone; 
 inhibitors of complex III at Q i  site selected from cyazofamid, amisulbrom, [(3 S,6 S, 7R, 8R)-8-benzyl-3-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate, [(3S,6S,7R,8R)-8-benzyl-3-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate, [(3S,6S,7R,8R)-8-benzyl-3-[(3-isobutoxycarbonyloxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate, [(3 S,6S,7R,8R)-8-benzyl-3-[[3-(1,3-benzodioxol-5-ylmethoxy)-4-methoxy-pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate, and (3S,6S,7R,8R)-3-[[(3-hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]-6-methyl-4,9-dioxo-8-(phenylmethyl)-1,5-dioxonan-7-yl 2-methylpropanoate; 
 inhibitors of complex II selected from: benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, N-(4′-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N-(2-(1,3,3-trimethyl-butyl)-phenyl)-1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide, 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(difluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, and 1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide; 
 other respiration inhibitors selected from diflumetorim, (5,8-difluoroquinazolin-4-yl)-{2-[2-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl}-amine, binapacryl, dinobuton, dinocap, fluazinam, ferimzone, fentin salts, ametoctradin, and silthiofam; 
   B) Sterol biosynthesis inhibitors
 C14 demethylase inhibitors selected from azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1-[rel-(2S; 3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-5-thiocyanato-1H-[1,2,4]triazole, 2-[rel-(2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-2H-[1,2,4]triazole-3-thiol, imazalil, pefurazoate, prochloraz, triflumizol, fenarimol, nuarimol, pyrifenox, and triforine; 
 Delta14-reductase inhibitors selected from aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph, fenpropidin, piperalin, and spiroxamine; 
 Inhibitors of 3-keto reductase selected from fenhexamid; 
   C) Nucleic acid synthesis inhibitors
 phenylamides or acyl amino acid fungicides selected from benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M, ofurace, and oxadixyl; 
 other nucleic acid synthesis inhibitors selected from hymexazole, octhilinone, oxolinic acid, bupirimate, 5-fluorocytosine, 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine, and 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine; 
   D) Inhibitors of cell division and cytoskeleton
 benzimidazole and thiophanate tubulin inhibitors selected from benomyl, carbendazim, fuberidazole, thiabendazole, and thiophanate-methyl; 
 triazolopyrimidines selected from 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine; 
 other cell division inhibitors selected from diethofencarb, ethaboxam, pencycuron, fluopicolide, zoxamide, metrafenone, and pyriofenone; 
   E) Inhibitors of amino acid and protein synthesis
 methionine synthesis inhibitors selected from cyprodinil, mepanipyrim, and pyrimethanil; 
 protein synthesis inhibitors selected from blasticidin-S, kasugamycin, kasugamycin hydrochloride-hydrate, mildiomycin, streptomycin, oxytetracyclin, polyoxine, and validamycin A; 
   F) Signal transduction inhibitors
 MAP/histidine kinase inhibitors selected from fluoroimid, iprodione, procymidone, vinclozolin, fenpiclonil, and fludioxonil; 
 G protein inhibitors selected from quinoxyfen; 
   G) Lipid and membrane synthesis inhibitors
 Phospholipid biosynthesis inhibitors selected from edifenphos, iprobenfos, pyrazophos, and isoprothiolane; 
 lipid peroxidation inhibitors selected from dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb, and etridiazole; 
 phospholipid biosynthesis and cell wall deposition inhibitors selected from: dimethomorph, flumorph, mandipropamid, pyrimorph, benthiavalicarb, iprovalicarb, valifenalate and N-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2-yl), and carbamic acid-(4-fluorophenyl) ester; 
 compounds affecting cell membrane permeability and fatty acids selected from propamocarb and propamocarb-hydrochlorid; 
 fatty acid amide hydrolase inhibitor selected from 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone; 
   H) Inhibitors with Multi-site Action
 inorganic active substances selected from Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur; 
 thio- and dithiocarbamates selected from ferbam, mancozeb, maneb, metam, metiram, propineb, thiram, zineb, and ziram; 
 organochlorine compounds selected from anilazine, chlorothalonil, captafol, captan, folpet, dichlofluanid, dichlorophen, flusulfamide, hexachlorobenzene, pentachlorphenole and its salts, phthalide, tolylfluanid, and N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methyl-benzenesulfonamide; 
 guanidines and other inhibitors with multi-site action selected from guanidine, dodine, dodine free base, guazatine, guazatine-acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate), dithianon, and 2,6-dimethyl-1H,5H[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetraone; 
   I) Cell wall synthesis inhibitors
 inhibitors of glucan synthesis selected from: validamycin and polyoxin B; 
 melanin synthesis inhibitors selected from pyroquilon, tricyclazole, carpropamid, dicyclomet, and fenoxanil; 
   J) Plant defence inducers selected from:
 acibenzolar-S-methyl, probenazole, isotianil, tiadinil, prohexadione-calcium; phosphonates: fosetyl, fosetyl-aluminum, and phosphorous acid and its salts; 
   K) Active substances with unknown mode of actions selected from:
 bronopol, chinomethionat, cyflufenamid, cymoxanil, dazomet, debacarb, diclomezine, difenzoquat, difenzoquat-methylsulfate, diphenylamin, fenpyrazamine, flumetover, flusulfamide, flutianil, methasulfocarb, nitrapyrin, nitrothal-isopropyl, oxathiapiprolin, oxin-copper, proquinazid, tebufloquin, tecloftalam, triazoxide, 2-butoxy-6-iodo-3-propylchromen-4-one, N-(cyclopropylmethoxyimino-(6-difluoromethoxy-2,3-difluoro-phenyl)-methyl)-2-phenyl acetamide, N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine, N′-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine, N′-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine, N′-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine, methoxy-acetic acid 6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester, 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine, 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine, N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide, 5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzoimidazole, and 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxyphenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide; 
   L) Antifungal biocontrol agents and plant bioactivators selected from:
   Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus pumilus, Bacillus subtilis, Bacillus subtilis  var.  amyloliquefaciens  FZB24,  Candida oleophila  I-82,  Candida saitoana, Chitosan, Clonostachys rosea  f.  catenulata, Coniothyrium minitans, Cryphonectria parasitica, Cryptococcus albidus, Fusarium oxysporum, Metschnikowia fructicola, Microdochium dimerum, Phlebiopsis gigantea, Pseudozyma flocculosa, Pythium oligandrum  DV74,  Reynoutria sachlinensis, Talaromyces flavus  V117b,  Trichoderma  asperellum SKT-1 , T. atroviride  LC52,  T. harzianum  T-22,  T. harzianum  TH 35,  T. harzianum  T-39,  T. harzianum  and  T. viride, T. harzianum  ICC012 and  T. viride  ICC080,  T. polysporum  and  T. harzianum, T. stromaticum, T. virens  GL-21,  T. viride, T. viride  TV1, and  Ulocladium oudemansii  HRU3; 
   M) Growth regulators selected from:
 abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat chloride, choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat chloride, naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione-calcium, prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate, 2,3,5-tri-iodobenzoic acid, and trinexapac-ethyl and uniconazole; 
   N) Herbicides
 acetamides selected from acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamid, pretilachlor, propachlor, and thenylchlor; 
 amino acid derivatives selected from bilanafos, glyphosate, glufosinate, and sulfosate; 
 aryloxyphenoxypropionates selected from clodinafop, cyhalofop-butyl, fenoxaprop, fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop, and quizalofop-P-tefuryl; 
 Bipyridyls selected from diquat and paraquat; 
 (thio)carbamates selected from asulam, butylate, carbetamide, desmedipham, dimepiperate, eptam, esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb, pyributicarb, thiobencarb, and triallate; 
 cyclohexanediones selected from butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, and tralkoxydim; 
 dinitroanilines selected from benfluralin, ethalfluralin, oryzalin, pendimethalin, prodiamine, and trifluralin; 
 diphenyl ethers selected from acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, and oxyfluorfen; 
 hydroxybenzonitriles selected from bomoxynil, dichlobenil, and ioxynil; 
 imidazolinones selected from imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, and imazethapyr; 
 phenoxy acetic acids selected from clomeprop, 2,4-dichlorophenoxyacetic acid, 2,4-DB, dichlorprop, MCPA, MCPA-thioethyl, MCPB, and Mecoprop; 
 pyrazines selected from chloridazon, flufenpyr-ethyl, fluthiacet, norflurazon, and pyridate; 
 pyridines selected from aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, picloram, picolinafen, and thiazopyr; 
 sulfonyl ureas selected from amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, mesosulfuron, metazosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, and 1-((2-chloro-6-propyl-imidazo[1,2-b]pyridazin-3-yl)sulfonyl)-3-(4,6-dimethoxy-pyrimidin-2-yl)urea; 
 triazines selected from ametryn, atrazine, cyanazine, dimethametryn, ethiozin, hexazinone, metamitron, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, and triaziflam; 
 ureas selected from chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron, methabenzthiazuron, and tebuthiuron; 
 other acetolactate synthase inhibitors selected from: bispyribac-sodium, cloransulam-methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, ortho-sulfamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyroxasulfone, and pyroxsulam; 
 other herbicides selected from amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin, bencarbazone, benfluresate, benzofenap, bentazone, benzobicyclon, bicyclopyrone, bromacil, bromobutide, butafenacil, butamifos, cafenstrole, carfentrazone, cinidon-ethyl, chlorthal, cinmethylin, clomazone, cumyluron, cyprosulfamide, dicamba, difenzoquat, diflufenzopyr,  Drechslera monoceras , endothal, ethofumesate, etobenzanid, fenoxasulfone, fentrazamide, flumiclorac-pentyl, flumioxazin, flupoxam, flurochloridone, flurtamone, indanofan, isoxaben, isoxaflutole, lenacil, propanil, propyzamide, quinclorac, quinmerac, mesotrione, methyl arsonic acid, naptalam, oxadiargyl, oxadiazon, oxaziclomefone, pentoxazone, pinoxaden, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazoxyfen, pyrazolynate, quinoclamine, saflufenacil, sulcotrione, sulfentrazone, terbacil, tefuryltrione, tembotrione, thiencarbazone, topramezone, (3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-phenoxy]-pyridin-2-yloxy)-acetic acid ethyl ester, 6-amino-5-chloro-2-cyclopropyl-pyrimidine-4-carboxylic acid methyl ester, 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-pyridazin-4-ol, 4-amino-3-chloro-6-(4-chloro-phenyl)-5-fluoro-pyridine-2-carboxylic acid, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid methyl ester, and 4-amino-3-chloro-6-(4-chloro-3-dimethylamino-2-fluoro-phenyl)-pyridine-2-carboxylic acid methyl ester; 
   O) Insecticides
 organo(thio)phosphates selected from acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos, trichlorfon; 
 carbamates selected from: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, and triazamate; 
 pyrethroids selected from: allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalothrin, permethrin, prallethrin, pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, and dimefluthrin; 
 insect growth regulators selected from a) chitin synthesis inhibitors selected from benzoylureas: chlorfluazuron, cyramazin, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, and clofentazine; b) ecdysone antagonists selected from halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, methoprene, and fenoxycarb; and d) lipid biosynthesis inhibitors selected from spirodiclofen, spiromesifen, and spirotetramat; 
 nicotinic receptor agonists/antagonists compounds selected from clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, and 1-(2-chloro-thiazol-5-ylmethyl)-2-nitrimino-3,5-dimethyl-[1,3,5]triazinane; 
 GABA antagonist compounds selected from endosulfan, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole, and 5-amino-1-(2,6-dichloro-4-methylphenyl)-4-sulfinamoyl-1H-pyrazole-3-carbothioic acid amide; 
 macrocyclic lactone insecticides selected from abamectin, emamectin, milbemectin, lepimectin, spinosad, and spinetoram; 
 mitochondrial electron transport inhibitor I acaricides selected from fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, and flufenerim; 
 METI II and III compounds selected from acequinocyl, fluacyprim, and hydramethylnon; 
 Uncouplers selected from chlorfenapyr; 
 oxidative phosphorylation inhibitors selected from cyhexatin, diafenthiuron, fenbutatin oxide, and propargite; 
 moulting disruptor compound selected from cryomazine; 
 mixed function oxidase inhibitor selected from piperonyl butoxide; 
 sodium channel blockers selected from indoxacarb and metaflumizone; 
 other insecticides selected from benclothiaz, bifenazate, cartap, flonicamid, pyridalyl, pymetrozine, sulfur, thiocyclam, flubendiamide, chlorantraniliprole, cyazypyr, cyenopyrafen, flupyrazofos, cyflumetofen, amidoflumet, imicyafos, bistrifluron, and pyrifluquinazon. 
   
     
     
         13 . The composition of  claim 10 , wherein R 1  in the compound of formula I is selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -chloroalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl and C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl. 
     
     
         14 . The composition of  claim 10 , wherein R 1  in the compound of formula I is methyl or ethyl. 
     
     
         15 . The composition of  claim 10 , wherein R 2  in the compound of formula I is hydrogen. 
     
     
         16 . A method for combating phytopathogenic fungi containing a mutation in the mitochondrial cytochrome b gene conferring resistance to Qo inhibitors, wherein the mutation is G143A, comprising applying a pesticidally effective amount of compound of formula (I) according to  claim 2 . 
     
     
         17 . The method of  claim 16 , wherein the phytopathogenic fungi are selected from the group consisting of  Alternaria alternata, Blumeria graminis, Pyricularia oryzae, Septoria tritici, Mycosphaerella fijiensis, Venturia inaequalis, Pyrenophora teres, Pyrenophora tritici - repentis  and  Plasmopara viticola.    
     
     
         18 . The method of  claim 17 , wherein the phytopathogenic fungus is  Septoria tritici.    
     
     
         19 . The method of  claim 16 , comprising:
 treating the phytopathogenic fungi or the materials, plants, the soil or seeds that are at risk of being diseased from phytopathogenic fungi with an effective amount of at least one compound of formula I, or a composition comprising it thereof.   
     
     
         20 . The method of  claim 19 , comprising:
 a) identifying the phytopathogenic fungi, or the materials, plants, the soil or seeds that are at risk of being diseased from phytopathogenic fungi, and   
       treating said fungi or the materials, plants, the soil or seeds with an effective amount of at least one compound of formula I, or a composition comprising it thereof. 
     
     
         21 : Agrochemical compositions wherein said compositions comprise an auxiliary and at least one compound of formula (I):
 wherein:   R 1  and R 2  together with the two carbon atoms linking them form a phenyl ring and   R 4  is 4-methyl-1,4-dihydro-tetrazol-5-one-1 yl, and
 wherein the abovementioned phenyl ring may carry 1, 2, 3 or up to the maximum number of identical or different groups R a  which independently of one another are selected from: 
   R a  CN, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl and C 1 -C 4 -haloalkoxy;   Y is a direct bond or a divalent group selected from —CH 2 —, —CH 2 CH 2 —, —C(Z)═N—O—CH 2 —, —CHZ—C(Z)═N—O—CH 2 —, —O—N═C(Z)—C(Z)═N—O—CH 2 —, —C(═O)—C(Z)═N—O—CH 2 — and —C(═N—O—Z)—C(Z)═N—O—CH 2 —,   where the bond depicted on the left side of the divalent group Y is attached to R 3 , and the bond depicted on the right side is attached to the carbon atom being substituted by R 2 , and   Z which may be the same or different to any other Z, is hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;   R 3  is   
       
         
           
           
               
               
           
         
         wherein # indicates the point of attachment to the linker moiety Y; 
         wherein the phenyl may carry 1, 2, 3 or up to the maximum possible number of identical or different groups R c , which may be the same or different to any other R c , is halogen 
         or an N-oxide or an agriculturally acceptable salt thereof, 
         and at least one further active substance selected from the classes A) and B): 
         A) Respiration inhibitors
 Inhibitors of complex III at Q o  site: coumethoxystrobin, coumoxystrobin, enestroburin, fenaminstrobin, fenoxystrobin/flufenoxystrobin, fluoxastrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, 2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic acid methyl ester and 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl-acetamide; 
 inhibitors of complex II: benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, N-(4′-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, N-(2-(1,3,3-trimethyl-butyl)-phenyl)-1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide, 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(difluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide; 
 other respiration inhibitors: diflumetorim, (5,8-difluoroquinazolin-4-yl)-{2-[2-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl}-amine; nitrophenyl derivates: binapacryl, dinobuton, dinocap, fluazinam; ferimzone; organometal compounds: fentin salts; ametoctradin; and silthiofam; and 
 
         B) Sterol biosynthesis inhibitors (SBI fungicides)
 C14 demethylase inhibitors: prothioconazole, simeconazole, 1-[rel-(2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-5-thiocyanato-1H-[1,2,4]triazole, 2-[rel-(2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-2H-[1,2,4]triazole-3-thiol. 
 
       
     
     
         21 : The agrochemical compositions of  claim 20 , wherein the further active substance is pyraclostrobin. 
     
     
         22 : The agrochemical compositions of  claim 20 , wherein the further active substance is selected from benzovindiflupyr, bixafen, boscalid, fluopyram, fluxapyroxad, isopyrazam, penflufen, penthiopyrad, sedaxane; ametoctradin and fluazinam. 
     
     
         23 : The agrochemical compositions of  claim 8 , wherein the further active substance is prothioconazole. 
     
     
         24 : The agrochemical compositions of  claim 20 , which comprise one compound of formula I as component 1) and one further active substance as component 2) and wherein the weight ratio of component 1) and component 2) is in the range of 1:20 to 20:1.