WO2008046856A2 - Compositions fongicides - Google Patents

Compositions fongicides Download PDF

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WO2008046856A2
WO2008046856A2 PCT/EP2007/061083 EP2007061083W WO2008046856A2 WO 2008046856 A2 WO2008046856 A2 WO 2008046856A2 EP 2007061083 W EP2007061083 W EP 2007061083W WO 2008046856 A2 WO2008046856 A2 WO 2008046856A2
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alkyl
methyl
formula
compounds
chloro
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PCT/EP2007/061083
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German (de)
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WO2008046856A3 (fr
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Reinhard Stierl
Bernd Müller
Jens Renner
Sarah Ulmschneider
Marianna Vrettou
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Basf Se
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to fungicidal compositions containing as active components
  • R 1 is -hydrogen, halogen, cyano, nitro, Ci-C8-alkyl, d-Cs-haloalkyl, d-Cs-H yd roxya I ky I, C 1 -Cs-Al koxy-C 1 -C 8 -a I ky I, C2-C8 AI ke ny I oxy-C 1 -C 8 -a I ky I, C2-C8-alkynyloxy-Ci-C 8 alkyl, C 3 -C 8 cycloalkyloxy-C 8 alkyl, Ci-C 8 - alkoxyalkyloxy-C 8 alkyl, benzyloxy-Ci-C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 - haloalkenyl, C 2 -C 8 -Al kinyl, C3-C8-haloalkynyl, Ci-C8-alkoxy
  • W 1 is S, O, NH, N-OH or N-OW 2 , where W 2 is C 1 -C 8 -alkyl or C 6 -C 14 -aryl-C 1 -C 8 -alkyl, where W 2 is one, two, may contain three or four identical or different groups R a ;
  • W 3 is hydrogen or C 1 -C 8 -alkyl
  • W 4 is C 1 -C 8 -alkyl, phenyl or phenylamino
  • W 5 is hydrogen, C 1 -C 6 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 3 -C 8 -cycloalkyl, benzyl, where W 5 is one, two, three or four identical or different Groups R a may contain;
  • W 6 , W 7 , W 8 are each independently:
  • W 6 is C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl, C 6 -C 4 -aryl, C 6 -C 4 -alkyl -Aryl-C 1 -C 8 -alkyl;
  • W 7 is hydrogen or one of the radicals mentioned at W 6 ;
  • two radicals W 7 or a radical W 7 and a radical W 6 can also together form a saturated or partially unsaturated cycle having 3, 4, 5 or 6 carbon atoms, the 1 or 2 further hetero atoms selected from nitrogen, sulfur and oxygen may contain;
  • W 8 is hydrogen, a cation, C 1 -C 8 -alkyl, C 2 -C 8 -alkynyl, C 2 -C 8 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl or C 6 -Ci4-aryl-Ci-C 8 alkyl;
  • W 6 , W 7 , W 8 or a cycle formed from W 7 or W 7 and W 6 may each independently contain one, two, three or four identical or different groups R a ;
  • R a means:
  • R a is halogen, cyano, nitro, hydroxy, carboxyl, Ci-C 8 alkyl, Ci-C 8 -HaIo- genalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 -Al kinyl, C 3 -C 8 - haloalkynyl, C4-Cio-alkadienyl, C 8 alkoxy, Ci-C 8 -Halogenalk- oxy, C 2 -C 8 alkenyloxy, C 2 -C 8 haloalkenyloxy, C 2 -C 8 alkynyloxy,
  • n 0, 1 or 2;
  • A, A ', A "independently of one another hydrogen, Ci-C 8 alkyl, C 2 -C 8 alkene yl, C 2 -C 8 -alkyl kinyl, C 3 -C 8 cycloalkyl, C 3 -C 8 Cycloalkenyl, phenyl, where the organic radicals may be partially or fully halogenated and / or monosubstituted or polysubstituted by nitro, cyanoato, cyano, C 1 -C 4 -alkoxy, and A and A may also be used together with the atoms to which they are attached represent a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group consisting of O, N and S.
  • R a may in turn carry one, two or three identical or different groups R b :
  • R b is halogen, cyano, nitro, hydroxy, mercapto, Ci-C 8 alkyl, C 2 -C 8 alkene yl, C 2 -C 8 -alkyl kinyl, d-do-alkadienyl, C 3 -C 8 - cycloalkyl, C 3 -C 8 -CyCIo- alkenyl, Cs-do-bicycloalkyl, C 8 alkoxy, C 2 -C 8 alkenyloxy, C 2 -C 8 - alkynyloxy, C 3 -C 8 cycloalkoxy, C 3 -C 8 -cycloalkenyloxy, Aminothiocar- carbonyl, d-Cs-alkyl-carbonyloxy, d-Cs-alkylaminothiocarbonyl, di-Ci- C 8 -alkylaminothiocarbonyl, C 8 alkylthio, Ci-
  • R 2 is hydrogen, halogen, cyano, Ci-C 8 alkyl, Ci-C8-haloalkyl, Ci-C 8 -AIk- oxy, Ci-C8-haloalkoxy, Ci-C8 alkylthio, Ci-C 8 - alkylsulfinyl, Ci-C 8 alkyl sulfonyl, C3-C8 cycloalkyl, C3-C8 halocycloalkyl; wherein R 2 may contain one, two, three or four identical or different groups R a
  • X is hydrogen, halogen, hydroxy, cyano, N (A ') A, C 8 alkoxy, Ci-C 8 genalkoxy -HaIo-, Ci-C8 alkylthio, Ci-C8-alkylsulfinyl, Ci-C 8 alkylsulfonyl, Ci-C 8 - alkyl, Ci-C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 -
  • Y is a five, six, seven, eight, nine or ten membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms selected from the group consisting of oxygen, nitrogen and
  • Phenyl which is unsubstituted or substituted by one, two, three, four or five identical or different substituents L;
  • L is halogen, cyano, nitro, hydroxy, cyanato (OCN), C 8 alkyl, C 8 - haloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 -Alkynyl, C 3 -C 8 -
  • a 1 is hydrogen, hydroxy, C 1 -C 8 -alkyl, C 1 -C 5 -haloalkyl, amino,
  • a 2 A 1 wherein one of said groups or NR 5 R 6, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 -alkyl kinyl, C 3 -C 8 haloalkynyl, d-
  • R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 independently of one another are hydrogen, C 1 -C 8 -alkyl, C 1 -C 5 -haloalkyl, C 2 -C 8 -alkynyl, C 2 -C 8 - haloalkenyl, C 2 -C 8 -alkyl kinyl, C3-C8-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8-halocycloalkyl, C3-Cs-cycloalkenyl or C3-C mean 8 halocycloalkenyl .
  • R 8 and R 9 , R 10 and R 11 and / or R 12 and R 13 may also together with the nitrogen atom to which they are attached form a four-, five- or six-membered saturated or partially unsaturated ring which is unsubstituted or is substituted with one, two, three or four identical or different substituents R a ;
  • L can carry one, two, three or four identical or different groups R L ;
  • R L is halogen, cyano, C 1 -C 8 -alkoxy, C 2 -C 8 -alkenyloxy, C 2 -C 5 -alkenyloxy, C 1 -C 8 -cycloalkyl, C 1 -C 8 -cycloalkenyl, C 1 -C 8 -cycloalkyloxy, C 3 -C 8 - cycloalkenyloxy, Ci-Cs-alkoximino, C 2 -C 8 -Alkenyloxyimino, C 2 -C 8 -Alkin- yloxyimino, Ci-C 8 -Alkoximino-C 8 alkyl, C 2 -C 8 -Alkenyloximino Ci- -C 8 alkyl, C 2 -C 8 alkynyloximino-Ci-C 8 alkyl;
  • R 4 is hydrogen, hydroxy or one of the meanings given for R 3 ;
  • R 3 and R 4 may also together with the nitrogen atom to which they are attached form a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two or three further heteroatoms from the group O, N and S as ring members may contain; in which
  • R 3 and / or R 4 or a heterocycle formed from R 3 and R 4 may carry one, two, three or four identical or different groups R a and / or two substituents bound to adjacent ring atoms for d-
  • Azoles selected from bitertanol, bromuconazole, cyproconazole, difenocynazole, diniconazole, enilconazole, epoxiconazole, fluquinconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole,
  • Carboxylic acid amides selected from carboxin, benalaxyl, benodanil, boscalid, fenfuram, fenhexamide, flutolanil, furametpyr, mepronil, metaldaxyl, mefenoxam, ofurace, oxadixyl, oxycarboxin, penthiopyrad, thifluzamide, tiadinil, 3,4-dichloro N- (2-cyanophenyl) -isothiazole-5-carboxylic acid amide, dimethomorph, flumorph, flumetover, fluopicolide (picobenzamide), zoxamide, carpropamide, diclocymet, mandipropamide, N- (2- (4- [3- (4-chloro - phenyl) -prop-2-ynyloxy] -3-methoxy-phenyl) -ethyl) -2-methanesulfony
  • X is hydrogen or fluorine
  • R 1 is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;
  • R 2 is hydrogen or halogen;
  • R 3, R 4 and R 5 are independently hydrogen, cyano, nitro, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C 4 - haloalkoxy, Ci-C4- Alkylthio or C 1 -C 4 haloalkyl;
  • Heterocyclic compounds selected from fluazinam, pyrifenox,
  • E 1 is C 3 -Ci2 alkyl, C 2 -C 2 -alkenyl, C 5 -C 2 -alkoxyalkyl, C 3 -C 6 cycloalkyl,
  • Haloalkyl C 3 -C 8 cycloalkyl, C 2 -Cio-alkenyl, C 2 -Cio-alkynyl, -C 6 - alkoxy, Ci-Ce-alkylthio, alkoxy-CRCE CRCE-alkyl, and NR A R B; in which
  • R A , R B independently of one another are hydrogen or C 1 -C 6 -alkyl; where the cyclic groups in E 1 and / or R a may carry one, two, three identical or different groups R b , which are selected independently of one another from: R b is halogen, cyano, hydroxyl, mercapto, nitro, NR A R B , Ci-Cio-alkyl,
  • E 3 is hydrogen, halogen, cyano, NR A R B , hydroxyl, mercapto, CrC 6 -
  • A is CH or N
  • Carbamates selected from Mancozeb, Maneb, Metam, Metiram, Ferbam, Propineb, Thiram, Zineb, Ziram, Diethofencarb, Iprovalicarb, Flubenthiavalicarb, Propamocarb, N- (1- (1 - (4-cyanophenyl) ethanesulfonyl-but - 2-yl) carbamic acid (4-fluorophenyl) ester, 3- (4-chloro-phenyl-3- (2-isopropoxycarbonylamino-3-methyl-butyrylamino-propanoic acid methyl ester of the formula VII
  • F) Other fungicides selected from guanidine, dodin, iminoctadine, iminoctadin triacetate, guazatine, guazatine acetate, antibiotics: kasugamycin, streptomycin, polyoxin, validamycin A, nitrophenyl derivatives: binapacryl, dinocap, dinobutone, sulfur-containing heterocyclyl compounds: dithionon, isoprothiolane, organometallic compounds : Fentin Salts, Organophosphorus Compounds: Edifenphos, Iprobenfos, Fosetyl, Fosetyl Aluminum, Phosphoric Acid and Their Salts, Pyrazophos, Tolclofosmethyl, Organochlorine Compounds: Chlorothalonil, Dichlofluanid, Flusulfamide, Hexachlorobenzene, Phthalide, Pencycuron, Quintozene, Thiophanate
  • Methyl, tolylfluanid, Inorganic agents Bordeaux broth, copper acetate, copper hydroxide, copper oxychloride, basic copper sulphate, sulfur, others: cyflufenamide, cymoxanil, dimethirimol, ethirimol, furalaxyl, metrafenone, spiroxamine, iminoctadine tris (albesilat), casagicycin hydrochloride hydrate, dichlorophen, pentachlorophenol and its
  • the invention relates to a method for controlling harmful fungi with a composition of at least one compound I and at least one of the active compounds II, the use of the compound (s) I with active ingredient (s) II for the preparation of such compositions and agents and seeds containing them Contain compositions.
  • the object of the present invention was to provide possibilities whereby an improved action against harmful fungi, in particular for certain indications, with a reduced total amount of applied active substances, can be achieved.
  • compositions of the compounds I and the active compounds II defined above were found. It has also been found that it is possible to combat harmful fungi more effectively in the simultaneous, joint or separate application of at least one compound I and of at least one of the active compounds II or the compound (s) I and at least one of the active compounds II with the individual compounds alone (synergistic compositions).
  • the compounds of the formula I used as component 1), their preparation and their action against harmful fungi are generally known from the literature (WO 02/48151, WO 04/000844, WO 05/000851, WO 05/056555, WO 05/056556, WO 05/056557, WO 05/056558, WO 05/056559, WO 05/082907). These compounds are known for controlling harmful fungi.
  • the active compounds II mentioned above as component 2), their preparation and their action against harmful fungi are generally known (cf., for example, http://www.hclrss.demon.co.uk/index.html); they are mostly commercially available:
  • Benalaxyl methyl N- (phenylacetyl) -N- (2,6-xylyl) -DL-alaninate (DE 29 03 612); Metalaxyl, methyl N- (methoxyacetyl) -N- (2,6-xylyl) -DL-alaninate (GB 15 00 581);
  • alkyl also includes octyl, decyl, tetradecyl and hexadecyl having a cis / trans ratio of 1: 1 [CAS RN 91315-15-0];
  • Dodemorph 4-cyclododecyl-2,6-dimethylmorpholine (DE-A 1198125); Fenpropimorph, (RS) -cis-4- [3- (4-tert-butylphenyl) -2-methylpropyl] -2,6-dimethylmorpholine (DE-A 27 52 096);
  • Guazatine composition of the reaction products obtained from the amidation of technical lminodi (octamethylene) diamine containing various guanidines and polyamines [CAS RN 108173-90-6];
  • Tridemorph, 2,6-dimethyl-4-tridecylmorpholine (DE-A 1 164 152);
  • Mepanipyrim (4-methyl-6-prop-1-ynyl-pymidin-2-yl) -phenylamine (EP-A 224 339); Cyprodinil, (4-cyclopropyl-6-methyl-pyridin-2-yl) -phenylamine (EP-A 310550);
  • Difenoconazole 1 - ⁇ 2- [2-chloro-4- (4-chlorophenoxy) phenyl] -4-methyl- [1,3-dioxolan-2-ylmethyl ⁇ -1 H- [1,2,4] triazole ( GB-A 2 098 607); Diniconazole, ( ⁇ E) - ⁇ - [(2,4-dichlorophenyl) methylene] - ⁇ - (1, 1-dimethylethyl) -1H-1, 2,4-triazole-1-ethanol (Noyaku Kagaku, 1983, Vol 8, p. 575);
  • Ipconazole 2 - [(4-chlorophenyl) methyl] -5- (1-methylethyl) -1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol (EP-A 267,778); Metconazole, 5- (4-chlorobenzyl) -2,2-dimethyl-1 - [1, 2,4] triazole-1-ylmethylcyclopentanol
  • Penconazole 1- [2- (2,4-dichlorophenyl) pentyl] -1 H- [1,2,4] triazole (Pesticide Manual, 12th Edition 2000, p. 712);
  • Triflumizole (4-chloro-2-trifluoromethylphenyl) - (2-propoxy-1 - [1, 2,4] triazole-1-yl-ethylidene) -amine (JP-A 79/1 19 462);
  • Ferbam iron (3+) dimethyldithiocarbamate (US 1,972,961); Nabam, disodium ethylenebis (dithiocarbamate) (US 2,317,765);
  • Metiram zinc ammonium ethylenebis (dithiocarbamate) (US 3,248,400); Propineb, zinc propylene bis (dithiocarbamate) polymer (BE 611 960);
  • Carbendazim (1 H-benzimidazol-2-yl) -carbamic acid methyl ester (US 3,657,443); Carboxin, 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide (US 3,249,499);
  • Cyazofamide 4-chloro-2-cyano-N, N-dimethyl-5- (4-methylphenyl) -1H-imidazole-1-sulfonamid CAS RN 120116-88-3]; Dazomet, 3,5-dimethyl-1,3,5-thiadiazinan-2-thione (Bull Soc Soc. Chim. Fr. Vol. 15, p.891
  • Furametpyr 5-chloro-N- (1,3-dihydro-1,1,3-trimethyl-4-isobenzofuranyl) -1,3-dimethyl-1H-pyrazole-4-carboxamide [CAS RN 123572-88-3 ]; Isoprothiolane, diisopropyl-1,3-dithiolan-2-ylidene malonate (Proc. Insectic, Fungic, Conf.
  • Tricyclazole 5-methyl-1,2,4-triazolo [3,4-b] [1,3] benzothiazole [CAS RN 41814-78-2];
  • Ethylhexyl and 1-propylpentyl is (US 2,526,660);
  • Nitrothal isopropyl, diisopropyl 5-nitroisophthalate Proc. Br. Insectic. Fungic. Conf.
  • Carpropamide 2,2-dichloro-N- [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methylcyclopropane carboxamide [CAS RN 104030-54-8]; Chlorothalonil, 2,4,5,6-tetrachloroisophthalonitrile (US 3,290,353);
  • Fosetyl Fosetyl Aluminum, Ethyl Phosphonate (FR 22 54 276); Iprovalicarb, [(1S) -2-methyl-1- (1-p-tolyl-ethylcarbamoyl) -propyl] -carbamic acid isopropyl ester (EP-A 472 996);
  • Penthiopyrad (RS) -N- [2- (1, 3-dimethylbutyl) -3-thienyl] -1-methyl-3- (trifluoromethyl) -1H-pyrazole-4-carboxamide (JP 10/130268); Propamocarb, 3- (dimethylamino) propylcarbaminklareisopropylester (DE-A 15 67 169);
  • Azoxystrobin 2- ⁇ 2- [6- (2-Cyano-1-vinyl-penta-1,3-dienyloxy) -pyrimidin-4-yloxy] -phenyl ⁇ -3-methoxy-acrylic acid methyl ester (EP-A 382 375) ;
  • Picoxystrobin 3-methoxy-2- [2- (6-trifluoromethyl-pyridin-2-yloxymethyl) -phenyl] -acrylic acid methyl ester (EP-A 278 595); Pyraclostrobin, N- ⁇ 2- [1- (4-chlorophenyl) -1H-pyrazol-3-yloxymethyl] phenyl ⁇ (N-methoxy) carbamic acid methyl ester (WO 96/01256);
  • Trifloxystrobin (E) -methoxyimino- ⁇ (E) - ⁇ - [1- ( ⁇ , ⁇ , ⁇ -trifluoro-m-tolyl) ethylideneaminooxy] -o-tolyl ⁇ -acetic acid methyl ester (EP-A 460 575); 2- [ortho- (2,5-dimethylphenyl-oxymethylene) phenyl] -3-methoxy-methyl acrylate
  • the 1-methyl-pyrazol-4-ylcarboxanilide of the formula III are known from the literature (see, for example, EP-A 545 099, EP-A 589 301, WO 99/09013, WO 2003/70705 and WO 2006/087343), and can produced by the methods described therein.
  • azolopyrimidin-7-ylamines of the formula VI their preparation and their action against harmful fungi are generally known from the literature (EP-A 71 792, EP-A 141 317, WO 03/009687, WO 05/087771, WO 05/087772 WO 05/087773; WO 2005/087772; WO 2006/087325; WO 2006/092428).
  • the compounds of the formula I can have one or more centers of chirality and are then present as enantiomer or diastereomer mixtures.
  • the invention relates to both fungicidal compositions containing the pure enantiomers or diastereomers or rotamers and mixtures thereof.
  • Suitable compounds of formula I also include all possible stereoisomers (cis / trans isomers) and mixtures thereof.
  • the compounds I used in the compositions according to the invention can be present in various crystal modifications, such compositions also being the subject of the present invention.
  • suitable agriculturally acceptable salts are, in particular, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the pesticidal action of the compounds used according to the invention.
  • the ions of the alkali metals preferably sodium or potassium, the alkaline earth metals, preferably calcium, magnesium or barium, the transition metals, preferably manganese, copper, zinc or iron, or the ammonium ion, the desired one to four (Ci-C4 ) -Alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri- (C 1 -C 4) -alkylsulfonium and sulfoxonium ions, preferably tri (Ci -C4) -alkylsulfoxonium, into consideration.
  • the alkali metals preferably sodium or potassium
  • the alkaline earth metals preferably calcium, magnesium or barium
  • the transition metals preferably manganes
  • Anions of advantageously usable acid addition salts are, for example, chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of (C 1 -C 4) -alkanoic acids, preferably formate , Acetate, propionate and butyrate. They can be formed by reaction of the compounds I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • Substituentenmaschine stand in composite groups.
  • the meaning (C n -C m) indicates the particular possible number of carbon atoms in the respective substituent or substituent part:
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyl and the alkyl moieties of composite groups such as alkylamino: saturated, straight-chain or branched hydrocarbon radicals having preferably 1 to 2, 4, 6, 8 or 10 carbon atoms, for example Ci-C ⁇ -alkyl such as methyl, ethyl, propyl, 1-methylethyl , Butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1 -Dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl , 2,3-dimethylbutyl, 3,3
  • the alkyl groups are substituted at least once or completely by a particular halogen atom, preferably fluoro, chloro or bromo. In a further embodiment, the alkyl groups are partially or completely halogenated by various halogen atoms; for mixed halogen substitutions, the combination of chlorine and fluorine is preferred.
  • (C 1 -C 4) -haloalkyl more preferably (C 1 -C 2) -haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1,1,1-trifluoroprop-2-yl;
  • Hydroxyalkyl Alkyl as mentioned above, wherein one or more hydrogen atoms are replaced by hydroxy (OH) groups.
  • Alkenyl and the alkenyl moieties in assembled groups such as alkenyloxy: unsaturated, straight-chain or branched hydrocarbon radicals preferably having 2 to 4, 2 to 6, 2 to 8 or 2 to 10 carbon atoms and one or two, preferably one, double bonds in any position.
  • alkenyl groups are C 2 -C 6 alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl 1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1 -butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl , 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl,
  • Alkadienyl unsaturated, straight-chain or branched hydrocarbon radicals having preferably 4 to 6, 4 to 8 or 4 to 10 carbon atoms and two double bonds in any position;
  • Alkynyl and the alkynyl moieties in compounded groups straight-chain or branched hydrocarbon groups having preferably 2 to 4, 2 to 6, 2 to 8 or 2 to 10 carbon atoms and one or two, preferably one, triple bonds in any position, e.g.
  • C 2 -C 6 -alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4- Pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2- propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl 3-pentynyl, 2-methyl-4-p
  • Haloalkynyl alkynyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;
  • Cycloalkyl and the cycloalkyl moieties in combined groups mono- or bicyclic, preferably monocyclic, saturated hydrocarbon groups having in particular 3 to 6, 3 to 8, 3 to 10 or 3 to 12 carbon ring members, e.g. C3-C6 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl;
  • Halogencycloalkyl cycloalkyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine;
  • Cycloalkenyl monocyclic, monounsaturated hydrocarbon groups having preferably 3 to 12, 3 to 10, 3 to 8 or 4 to 6, in particular 5 to 6 carbon ring members, such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, Cyclohexene-3-yl, cyclohexene-4-yl and the like;
  • Halocycloalkenyl cycloalkenyl as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms as described above under haloalkyl, in particular fluorine, chlorine or bromine; Alkoxy: for an oxygen-bonded alkyl group as defined above, preferably having 1 to 8, more preferably 2 to 6 carbon atoms.
  • Examples of preferred alkoxy groups are: methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy; and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3 Methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1, 2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;
  • Haloalkoxy alkoxy, as defined above, wherein in these groups the hydrogen atoms are partially or completely replaced by halogen atoms, as described above under haloalkyl, in particular fluorine, chlorine or bromine.
  • haloalkoxy radicals are OCH 2 F, OCHF 2 , OCF 3 , OCH 2 Cl, OCHCl 2 , OCCl 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2 , 2-Difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC 2 F 5 , 2-fluoro
  • Alkenyloxy Alkenyl as defined above, which is bonded via an oxygen atom. Preferred are (C 2 -C 8) alkenyloxy, more preferably (C 3 -C 6) alkenyloxy;
  • Alkylene divalent linear chains of CH 2 groups. Preference is given to (C 1 -C 6) -alkylene, more preferably (C 2 -C 4) -alkylene, and furthermore it may be preferred to use (C 1 -C 3 ) -alkylene groups.
  • Examples of preferred alkylene radicals are CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 (CHz) 2 CH 2 , CH 2 (CH 2 ) 3 CH 2 and CH 2 (CH 2 ) 4 CH 2 ;
  • Oxyalkylene Alkylene, as defined above, preferably having 2 to 4 CH 2 groups, wherein a valence is bonded to the skeleton via an oxygen atom.
  • Examples of preferred oxyalkylene radicals are OCH 2 , OCH 2 CH 2 , OCH 2 CH 2 CH 2 and OCH 2 (CH 2 ) 2 CH 2 ;
  • Oxyalkylenoxy Alkylene, as defined above, preferably having 1 to 3 CH 2 groups, wherein both valences are bonded to the skeleton via an oxygen atom.
  • Examples of preferred oxyalkyleneoxy radicals are OCH 2 O, OCH 2 CH 2 O and OCH 2 CH 2 CH 2 O;
  • Alkylthio alkyl as defined above attached via an S atom;
  • Alkylsulfinyl alkyl as defined above which is bonded through an SO group
  • Alkylsulfonyl alkyl as defined above attached via an S (O) 2 group;
  • the respective heterocycle may be attached via a carbon atom or via a nitrogen atom, if present. It may be preferred according to the invention that the respective heterocycle is bonded via carbon, on the other hand it may also be preferred that the heterocycle is bonded via nitrogen.
  • the heterocycle means in particular:
  • 5-membered heteroaryl containing one, two, three or four nitrogen atoms or one, two or three nitrogen atoms and / or a sulfur or oxygen atom which may be attached via C or N; or
  • 6-membered heteroaryl containing one, two, three or four, preferably one, two or three, nitrogen atoms which may be attached via C or N;
  • 5-membered heteroaryl containing one, two, three or four nitrogen atoms or one, two or three nitrogen atoms and / or a sulfur or oxygen atom, which heteroaryl may be attached via C or N, if present: 5-membered heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and / or one sulfur or oxygen atom as ring members, eg Furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (1,2,3-; 1,2,4-triazolyl), tetrazolyl, oxazolyl, isoxazolyl, 1,3,4-oxadiazolyl, thiazolyl, isothiazolyl and thiadiazolyl, in particular 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl,
  • 6-membered heteroaryl containing one, two, three or four, preferably one, two or three nitrogen atoms, wherein the heteroaryl can be attached via C or N, if present: 6-membered heteroaryl groups which, in addition to carbon atoms, have one to four or may contain one to three nitrogen atoms as ring members, eg Pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1, 2,3-triazinyl, 1, 2,4-triazinyl, 1, 3,5-triazinyl, especially 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4 Pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1, 3,5-triazin-2-yl and 1, 2,4-triazin-3-yl.
  • 6-membered heteroaryl groups which, in addition to carbon atoms
  • Aryl aromatic hydrocarbon cycles, in particular having 6 to 14, preferably 6 to 10 carbon atoms. Phenyl (C 6 H 5 -) are preferred according to the rule and naphthyl (C 0 H 7 -).
  • R 1 is not hydrogen
  • R 1 is halogen, cyano, nitro, Ci-C ⁇ alkyl, Ci-C8-haloalkyl, Ci-C8-hydroxyalkyl, d-Cs-alkoxy-d-Cs-alkyl, C2-C 8 alkenyloxy-Ci-C8 alkyl, C2-C8-alkynyloxy-Ci-C 8 alkyl, C 3 -C 8 cycloalkyloxy-Ci-C 8 - alkyl, Ci-C 8 -Alkoxyalkyloxy-C 8 -alkyl, benzyloxy-Ci-C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 - haloalkenyl, C 2 -C 8 -alkyl kinyl, C3-C8-haloalkynyl, Ci-C 8 - alkoxy, Ci-C 8 -Halogenalk-
  • R 1 is C 1 -C 8 -alkoxyimino-C 1 -C 8 -alkyl, where the alkyl radical may be substituted by R a .
  • W 4 here means phenylamino, which may be mono- to trisubstituted by identical or different substituents chosen from Ci-C4 -alkyl, Ci-C 4 alkoxy, halogen, nitro and / or Ci-C 4 haloalkyl having 1 to 5 halogen atoms.
  • W 3 is hydrogen, methyl or ethyl and W 4 is C 1 -C 2 -alkyl, where any of the alkyl radicals may be substituted by methoxy, ethoxy, methylcarbonyl, ethylcarbonyl, methoxycarbonyl or ethoxycarbonyl.
  • W 4 is phenyl, which may be monosubstituted to trisubstituted by identical or different methyl, ethyl, methoxy, ethoxy, fluoro, chloro, bromo, nitro and / or trifluoromethyl, or W 4 is phenylamino, which is simple may be substituted by three or more identical or different by methyl, ethyl, methoxy, ethoxy, fluorine, chlorine, bromine, nitro and / or trifluoromethyl.
  • W represents Ci-C6 haloalkyl 5, C 2 -C 6 alkenyl, C 2 -CE kinyl Al, Cs-C ⁇ cycloalkyl or benzyl, in particular C 4 d- haloalkyl, C3-Cs-alkenyl, C3 C5-Al kinyl, cyclopropyl, cyclopentyl, cyclohexyl or benzyl, preferably CF3, CCI3, AIIyI, propargyl, cyclopropyl or benzyl.
  • R 1 is CONW 6 W 7 , CONW 7 -N (W 7 ) 2 , CO-NW 7 -OW 7 , COOW 8 , C (S) OW 7 , C (O) SW 7 , C (S) SW 7 , SW 7 , SOW 7 , SO 2 W 7 , SO 3 W 7 , SON (W 7 ) 2 , SO 2 N (W 7 ) 2 , P (O) (OW 7 ) 2 , NW 7 OW 7, B (OW 7) 2, - (CW 7 2) o- 6 7 -NW 2 or - (CW 2 7) 0 - 6. -NW -NW 7 7 2; where W 6 , W 7 , W 8 are each independently:
  • Ci-Cio-alkyl C 2 -Cio-alkenyl, C 2 -Cio-alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, C 6 -Ci4-aryl, C 6 -C 4 -Aryl-C 1 -C 8 -alkyl;
  • W 7 is hydrogen or one of the radicals mentioned at W 6 ; two radicals W 7 or a radical W 7 and a radical W 6 may also together form a saturated or partially unsaturated radical. form saturated cycle having 3, 4, 5 or 6 carbon atoms, which may contain 1 or 2 further heteroatoms selected from nitrogen, sulfur and oxygen;
  • W 8 is hydrogen, a cation, Ci -C 8 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkyl kinyl, C 3 -C 8 cycloalkyl, Cs-Cs-cycloalkenyl, or C 6 - Ci4-aryl-Ci-C 8 alkyl;
  • W 6 , W 7 , W 8 or a cycle formed from W 7 or W 7 and W 6 may each independently contain one, two, three or four identical or different groups R a .
  • R 1 is CONW 6 W 7 .
  • R 1 is cyano, fluorine, chlorine, bromine, iodine, nitro, formyl, C 1 -C 6 -haloalkyl having one to nine halogen atoms independently selected from fluorine, chlorine and bromine, C 1 -C 4 -alkyl, C 2 C6-alkenyl, C 2 -C -alkenyl substituted by carboxy, methoxycarbonyl or ethoxycarbonyl, C 2 -C 6 -alkynyl, preferably C 2 -C -alkenyl, C 2 -C -alkenyl substituted by carboxy, methoxycarbonyl or ethoxycarbonyl , preferably C 2 -C -alkenyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -cycloalkyl,
  • R 1 is cyano, fluorine, chlorine, bromine, iodine, nitro, formyl, C 1 -C 4 -haloalkyl having one to nine halogen atoms selected independently from fluorine, chlorine and bromine, C 1 -C 4 -alkyl, Cs-C ⁇ -cycloalkyl, thiocarbamoyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -hydroximinoalkyl or C 1 -C 4 -alkoxyimino-C 1 -C 4 -alkyl.
  • R 1 is cyano, fluorine, chlorine, bromine, iodine, nitro, formyl, trifluoromethyl, difluoromethyl, methoxycarbonyl, methylcarbonyl, ethylcarbonyl, hydroximinomethyl, methoximinomethyl, thiocarbamoyl, methyl, ethyl, cyclopropyl, methylthio , Methylsulfinyl, methylsulfonyl, methylaminocar- bonyl, hydroxymethyl, hydroxyeth-1-yl, methoxymethyl, ethoxymethyl or 1-methoxy-ethyl.
  • R 1 is cyano, fluorine, chlorine, bromine, iodine, formyl, trifluoromethyl, methoxycarbonyl, methylcarbonyl, hydroximinomethyl, methoximinomethyl, thiocarbamoyl, nitro, methyl, ethyl or cyclopropyl.
  • Particular embodiments of R 1 are in particular cyano, fluorine, chlorine, bromine, iodine, nitro, formyl, methyl, cyclopropyl, thiocarbamoyl and methoximinomethyl.
  • R 1 represents -C (W 9 ) (W 10 ) OW 11 , where W 9 , W 10 , W 11 mean:
  • W 9, W 10, W 11 are independently hydrogen, Ci-C 8 alkyl, Ci-C8-haloalkyl, d-C ⁇ -alkoxyalkyl, C 2 -C 8 alkenyl, C 2 -C 8 -alkyl kinyl, C C 3 -C 8 cycloalkyl, benzyl; W 9 , W 10 , W 11 may each independently contain one, two, three or four identical or different groups R a , wherein R a is as herein defined or preferably defined;
  • W 10 and OW 11 may also together form a group # -O- (CH 2 ) p -O- #, wherein p is 1, 2, 3, 4 or 5 and the alkylene chain contains one, two or three substituents R a may be as defined herein, wherein R a is particularly independently selected from methyl, ethyl, hydroxy, methoxy, ethoxy, hydroxymethyl, methoxymethyl and ethoxymethyl.
  • W 9, W 10, W 11 are independently hydrogen, -C 4 -alkyl, Ci-C 4 haloalkyl, C 3 -C 6 cycloalkyl, Ci-C 2 alkoxy-d- C 4 alkyl C 2 -C 5 alkenyl, C 2 -C 5 alkynyl or benzyl; or W 10 and OW 11 together form # -O-CH 2 -CH 2 -O- #, wherein the alkylene chain may contain one or two substituents R a , wherein R a is independently selected from methyl, ethyl, hydroxy, methoxy , Ethoxy, hydroxymethyl, methoxymethyl and ethoxymethyl.
  • W 9 , W 10 , W 11 independently of one another are hydrogen, methyl, ethyl, propyl, methoxymethyl, methoxyethyl, C 3 -C 4 -alkenyl, C 3 -C 4 -alkynyl or benzyl; or W 10 and OW 11 together form # -O-CH 2 -CH 2 -O- #, wherein the alkylene chain may contain one or two substituents R a , wherein R a is independently selected from methyl, ethyl, hydroxy, methoxy, ethoxy , Hydroxymethyl, methoxymethyl and ethoxymethyl.
  • R 1 is C 2 -C 8 alkenyl or C 2 -C 8 alkynyl, which may contain one, two, three or four identical or different groups R a .
  • R 1 means optionally substituted by R a C2-C6 alkenyl or C2-C6-alkynyl, preferably C2-C4-alkenyl, the carbonyl by carboxyl, Mehoxycar-, ethoxycarbonyl, formyl or halogen, or C2-C4 alkynyl which is substituted by carboxyl, mehoxycarbonyl, ethoxycarbonyl, formyl or halogen.
  • R 1 is saturated, partially unsaturated or aromatic 5- or ⁇ -membered heterocyclyl which may contain one, two, three or four identical or different groups R a .
  • R 1 stands for:
  • B, D, E, G, L are independently CW 12 , CW 12 W 13 , N, NW 12 , O or S, provided that at least one symbol is N, O or S and O is not adjacent and wherein V is C, CW 12 or N and W 12 and W 13 independently of one another are W 7 , halogen, NW 7 2, OH, SW 7 or OW 7 .
  • W 6 is preferably, in the above embodiments denotes Ci-Cio-alkyl, C 2 -Cio-alkenyl, C 2 -Cio-alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, phenyl-Ci-Cio - alkyl, wherein W 6 is unsubstituted or partially or completely halogenated and / or optionally carries one to three radicals from the group R a , or W 6 is Ci-Cio-haloalkyl, optionally one to three radicals from the group R a and wherein R a is preferably independently selected from cyano, nitro, hydroxy, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, d
  • W 7 in the abovementioned embodiments is preferably hydrogen, W 6 or two radicals W 7 or a radical W 7 and a radical W 6 together form a cycle having 3 to 6 carbon atoms which is saturated or partially unsaturated and is unsubstituted or or two further heteroatoms selected from N, S and O, wherein O atoms may not be adjacent.
  • W 8 in the abovementioned embodiments is preferably hydrogen, an alkali or alkaline earth metal cation, Cu cation, NH 4 + , mono (C 1 -C 10) alkylammonium, di (C 1 -C 10) alkylammonium, tri (C 1 -C 10) -alkylammonium, Tetra (Ci-Cio) alkylammonium, wherein the alkyl substituents of the ammonium ions can optionally be substituted by aryl or hydroxy, cholinium, C2-Cio-alkenyl, C2-Cio-alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkenyl wherein W 8 is unsubstituted or partially or fully halogenated and / or optionally carries one to three radicals from the group R a , or W 8 is Ci-Cio-halo genalkyl, the optionally one to three
  • R 1 represents # -CONW 6 W 7 , # -CONW 7 -N (W 7 ) 2 , # -CO-NW 7 -OW 7 , # -COOW 8 , # -C (S) OW 7 , # -C (O) SW 7 , # -SW 7 , # -SOW 7 , # -SO 2 W 7 , # -SO 3 W 7 , # -SON (W 7 ) 2 , # -P (O ) (OW 7 ) 2 , B (OW 7 ) 2 , pyrrolyl, imidazolinyl, pyrazolyl, 1, 3,4-triazolyl, thiazolyl, 1, 3, 4-oxadiazolyl, 1, 3,4-thiadiazolyl, oxazolyl, Tetrazolyl, oxadiazinyl, 4H- [1,2,4] oxadiazin-3-yl, dioxazinyl, dioxazinyl
  • W 6 in the abovementioned embodiments is preferably selected from C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 1 -C 6 -cycloalkyl, benzyl, CONW 7 OW 7 , COOW 8 , carboxy-d-d-alkyl and CN.
  • W 7 in the abovementioned embodiments is preferably selected from hydrogen and W 6 , or two radicals W 7 or a radical W 7 and a radical W 6 together form a cycle, as defined above.
  • W 8 in the abovementioned embodiments is preferably selected from among hydrogen, Na + , K + , 1 ⁇ 2Ca 2+ , 1 ⁇ 2Mg 2+ , Cu + , NH 4 + , [NH (CH 3 ) S] + , [N (CH 3 ) 4 ] + , [HN (C 2 H 5 ) 3 ] + , [N (C 2 H 5 ) 4 ] + , [H 2 N (iC 3 H 7 ) 2 ] + , [H 3 NCH 2 Ph] + , [(H 3 C) NCH 2 Ph] + , [H 2 N (benzyl) 2 ] + , [H 3 N (benzyl)] + optionally in whole or in part by F and / or Cl, CONW 6 W 7 ,
  • R 1 means according to another embodiment # -CONW 6 W 7 , # -CONW 7 "N (W 7 ) 2 , # -CO-NW 7 -OW 7 , # -C00W 8 , # -SW 7 , # -SOW 7 , -SO 2 W 7 , # -SO 3 W 7 , # -SON (W 7 ) 2 , # - P (O) (OW 7 ) 2 , 1 H-pyrrolyl, 1 H-imidazolyl, 1, 3, 4-oxadiazolyl, 1H-pyrazolyl-1H-1, 3,4-triazolyl, tetrazolyl, oxadiazinyl, 4H- [1, 2,4] oxadiazin-3-yl, dioxazinyl, 5,6-dihydro- [1, 4,2] -dioxyzine-3-yl, pyridyl, where the heterocyclic radicals are optionally substituted by one or more radicals independently
  • W 6 is C 1 -C 8 -alkyl, C 3 -C 6 -alkenyl, C 1 -C 8 -cycloalkyl, benzyl, carboxy-C 1 -C 4 -alkyl;
  • W 7 is hydrogen or W 6 or or two radicals W 7 or a radical W 7 and a radical W 6 together form a cycle, as defined above;
  • R 1 is selected from CO-NH-CH 3 , CON (CH 2 ) 2 , CONH (IC 3 H 7 ), CO-morpholin-1-yl, COOH, COO-propen-3-yl, COO-benzyl, COOCH 2 CH 2 OCH 3 , SO 3 H, SO 2 CH 3 , COO-K + , COO-Na + , CONCH 3 OCH 3 , COOCH (CH 3 ) COOCH 3 , COOCH 2 CH 2 OCH 2 CH 2 OCH 3 , COOCH 2 CH 2 OCH 3 , COOCH 2 COOCH 3 , COOC 2 H 5 , COOCH 2 CF 3 , CONHCH (CH 3 ) COOCH 3 , CONHCH 2 COOCH 3 , (R) COOCH (CH 3 ) CONHCH 3 , COOCH 2 CH 2 OCH 2 CH 2 OCH 3 COOCH 2 CONCH 3 OCH 3 , 2-pyridyl,
  • R 1 is selected from CO-NH-CH 3 , CON (CH 2 ) 2 , CONH (IC 3 H 7 ), CO-morpholin-1-yl, COOH, COO-propen-3-yl, COO-benzyl, COOCH 2 CH 2 OCHS, SO 3 H, SO 2 CH 3 , COO K + , COO "Na + , COOCH 2 CH 2 OCHS, COOCH 2 COOCHS, COOC 2 H 5 , CONHCH 2 COOCHS, 2-pyridyl , 3-CH 3 -1, 2,4-triazol-5-yl, CONCH 3 OCH 3 , CONH (CH 2 ) 2 OCH 3 , CONHCH 2 CN, COOPhenyl, CONHC (CH 3 ) 2 -C ⁇ CH , CONHOH, COO-NH 4 + , 1, 3,4-oxathiazol-2-one-5-yl, 5-aminothiadiazol-2-y
  • R 1 is selected from CO-NH-CH 3 , CON (CH 3 ) 2 , CONH (iC 3 H 7 ), COOH, COO-benzyl, COOCH 2 CH 2 OCH 3 , SO 3 H , SO 2 CH 3 , COO K + , COO-Na + , COOC 2 H 5 , 2-pyridyl, 3-CH 3 -1, 2,4-triazol-5-yl, CONCH 3 OCH 3 , COOPhenyl, CONHOH, COO-NH 4 + , 1, 3,4-oxathiazol-2-one-5-yl, 5-aminothiadiazol-2-yl, CONHCH 2 CH 2 OH, NH 2 , oxadiazin-3-yl, oxazol-2-yl , SO 2 NCH (CH 2 ) 2 , COOH-C 3 H 7 , CONHOH, COO-propen-3-yl, NO 2 , CONHCH 2 CO
  • the other substituents according to formula I preferably have the meanings described herein as preferred, in particular compositions which as component 1) at least one compound selected from the compounds of the formulas Ia.1, La.2, Ia.3, La.4, Ia.5, Ia.6, Ia.7, Ia.8, Ia.9, Ia.10, Ia.1 1, Ia.12, Ia.13 and Ia.14, object of this invention, wherein the substituents Y and Z have the meanings and combinations of meanings as given for the compounds in Tables 1 to 257, and R 1 has one of the meanings of the embodiments just described.
  • R 1 is hydrogen, fluorine, chlorine or bromine, in particular hydrogen.
  • R 1 is cyano
  • R 2 is cyano, fluorine, chlorine, bromine, iodine, nitro, formyl, C 1 -C 4 -haloalkyl having 1 to 9 halogen atoms, independently selected from fluorine, chlorine and bromine, C 1 -C 4 -alkyl, C 3-C6-cycloalkyl, thiocarbamoyl, -C 4 - alkoxycarbonyl, Ci-C4-alkylcarbonyl, hydroxyimino-Ci-C4-alkyl or Ci -C 4 -alkyl koxyimino- Ci-C 4 alkyl.
  • R 2 is hydrogen. In another embodiment, R 2 is cyano.
  • R 1 and R 2 each represent are each hydrogen, cyano, halogen or Ci-C 4 -AlkVl, and in one embodiment both mean hydrogen.
  • R 1 is CN and R 2 is hydrogen.
  • X in the compounds of the formula I is halogen, cyano, -C 4 -alkoxy, CrC 4 - haloalkoxy, Ci-C4-alkyl or Ci-C 4 haloalkyl.
  • X denotes C 1 -C 4 -alkyl, in particular methyl, ethyl, isopropyl or n-propyl. According to a specific embodiment, X is methyl.
  • X is C 1 -C 4 -haloalkyl, in particular halomethyl, such as, for example, fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorofluoromethyl, dichlorofluoromethyl or chlorodifluoromethyl.
  • halomethyl such as, for example, fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorofluoromethyl, dichlorofluoromethyl or chlorodifluoromethyl.
  • X is C 2 -C 6 -alkenyl or C 2 -C 6 -haloalkenyl, preferably C 2 -C 4 -alkenyl or C 2 -C 4 -haloalkenyl.
  • X is halogen, in particular chlorine or fluorine, especially chlorine.
  • X is C 1 -C 4 -alkoxy, in particular methoxy or ethoxy. Furthermore, X is preferably C 1 -C 4 -haloalkoxy.
  • X is cyano
  • Y when Y is a heteroaromatic or aromatic radical, Y contains at least one substituent L which is preferably ortho to the point of attachment to the skeleton of the compounds of the formula I.
  • each L is independently:
  • Ci-Cs-alkylcarbonyl Ci-Cs-alkylthiocarbonyl
  • L is C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl, more preferably C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, in particular methyl or ethyl, more preferably methyl.
  • L when it is bonded to a ring nitrogen of Y, is particularly preferably C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, -COO (C 1 -C 4 ), -CONH 2 or -CSNH 2 , in particular methyl, ethyl, isopropyl, cyclopropyl or -COOCH 3.
  • L is attached to a ring carbon of Y and unless otherwise specified, L is preferably each independently:
  • Ci-Cs-alkylcarbonyl Ci-Cs-alkylthiocarbonyl
  • Y may contain one to four, one to three, or one or two identical or different substituents L. According to one embodiment, Y contains the same substituents L. Y preferably contains one or two substituents L, more preferably one or two identical substituents L. Furthermore, Y preferably has two identical substituents L.
  • Y is a five, six, seven, eight, nine or ten membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms selected from the group consisting of oxygen, Nitrogen and sulfur, wherein the heterocycle is unsubstituted or substituted by one, two, three or four identical or different substituents L.
  • the heterocycle is attached via carbon to the backbone of the compounds of formula I.
  • the heterocycle is bonded to the skeleton of the compounds of the formula I via nitrogen. This also applies to the further embodiments of this embodiment of the invention described below.
  • the heterocycle contains at least one nitrogen atom as ring member.
  • Y is a saturated, fully unsaturated, fully or partially unsaturated or aromatic heterocyclyl containing one, two or three heteroatoms from the group consisting of oxygen, nitrogen and sulfur, wherein the Heterocycle is unsubstituted or substituted by one or two identical or different substituents L, which are preferably independently selected from halogen, hydroxy, mercapto, cyano, nitro, carboxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkyl, C 1 -C 4 - AIkOXy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio and C 3 -C 6 -cycloalkyl.
  • substituents L are preferably independently selected from halogen, hydroxy, mercapto, cyano, nitro, carboxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkyl, C 1 -C 4 - AIkOXy, Ci-
  • Y is an unsubstituted or substituted five-, six-, seven-, eight-, nine- or ten-membered saturated or partially unsaturated heterocycle containing one, two or three heteroatoms from the group O, N and S as
  • Y preferably contains an unsubstituted or substituted five-, six- or seven-membered saturated or partially unsaturated heterocycle which contains one, two or three nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms
  • the heterocycle contains one or two nitrogen atoms.
  • Partially unsaturated means that the heterocycle does not form an aromatic system, wherein the heterocycle preferably contains one or two double bonds.
  • Y represents N-piperidinyl or N-morpholinyl which are unsubstituted or substituted by one, two, three or four substituents L independently selected from fluoro, chloro, bromo, cyano, nitro, hydroxy, mercapto, methyl , Ethyl, methoxy, methylthio, hydroximinomethyl, hydroxyminoethyl, methoximinomethyl, methoxyiminoethyl and trifluoromethyl.
  • the invention relates to compositions containing as component 1) at least one compound I in which Y is an optionally substituted by L aromatic heterocycle, preferably a five- or six-membered aromatic heterocycle.
  • Y contains at least one ring nitrogen atom. It may be preferred that the binding site of Y to the skeleton of the formula I is in the ortho-position to the at least one nitrogen atom.
  • the heteroaryl (Y) has at least one substituent which is in the ortho position to the point of attachment to the skeleton of the formula I to which Y is bonded. It may be particularly preferred if the ortho-L is fluorine, chlorine, (Ci-C2) -alkyl, such as Methyl or ethyl, Ci-C2-fluoroalkyl such as trifluoroalkyl or Ci-C2-alkoxy such as methoxy.
  • Y is a 5-membered heteroaryl radical containing at least one nitrogen atom as ring member and optionally one or two further heteroatoms as ring members selected from O, S and N, which is unsubstituted or substituted by one, two or three Substituents L.
  • these are pyrrolyl, pyrazolyl, imidazolyl, 1, 2,3-triazolyl, 1, 2,4-triazolyl, oxazolyl, thiazolyl, isoxazolyl and isothiazolyl, which are unsubstituted or carry 1, 2 or 3 substituents L. can.
  • Y is preferably thiazolyl, imidazolyl, pyrazolyl, 1,2,4-triazolyl or 1,2,3-triazolyl, in particular pyrazol-1-yl, which are unsubstituted or carry one, two or three identical or different substituents L.
  • Y is thienyl.
  • Y is N-tetrazolyl, N-pyrazolyl, N-imidazolyl, N-1, 2,4-triazolyl or N-pyrrolyl which are unsubstituted or substituted by one, two, three or four substituents L. independently selected from fluorine, chlorine, bromine, cyano, nitro, hydroxy, mercapto, methyl, ethyl, methoxy, methylthio, hydroxyiminomethyl, hydroximinoethyl, methoximinomethyl, methoxyiminoethyl and trifluoromethyl.
  • thiazol-4-yl thiazol-2-yl, thiazol-5-yl, each of which is unsubstituted or containing one, two or three identical or different substituents independently selected from fluoro, chloro, bromo, cyano, nitro, Methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroxyiminoethyl, methoxyiminomethyl, methoxyimi- noethyl and trifluoromethyl; specific examples of this embodiment of the invention are 2-methylthiazol-4-yl, 2-methyl-5-bromothiazol-4-yl, 2-methyl-5-chlorothiazol-4-yl, 2,5-dichlorothiazol-4-yl;
  • 2-thienyl, 3-thienyl each of which is unsubstituted or containing one, two or three identical or different substituents independently selected from fluoro, chloro, bromo, cyano, nitro, methyl, ethyl, methoxy, methylthio, hydroximi- nomethyl, hydroxyiminoethyl, methoxyiminomethyl, methoxyiminoethyl and trifluoromethyl; specific examples of this embodiment of the invention are 5-methylthiophen-2-yl, 5-chlorothiophen-2-yl, 5-bromothiophen-2-yl, 3,5-dichlorothiophen-2-yl, 3,4,5-trichlorothiophene 2-yl, 5-bromothiophen-2-yl, 2-methylthiophen-3-yl, 2,5-dichlorothiophen-3-yl, 2,4,5-trichlorothiophen-3-yl and 2,5-dibromothiophene-3
  • Y is thiazolyl, imidazolyl, pyrazolyl, 1, 2,4-triazolyl or 1, 2,3-triazolyl and especially pyrazol-1-yl, where the abovementioned radicals are unsubstituted or 1, 2 or Have 3 substituents L.
  • Y is in particular one of the radicals Het-1 to Het-31 given below:
  • L 1 , L 2 , and L 3 are independently hydrogen or have one of the meanings given for L.
  • the radicals L 1 , L 2 and L 3 are independently selected from hydrogen, halogen, nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, especially C 1 -C 2 -fluoroalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -alkoxycarbonyl.
  • L 1 , L 2 and L 3 are independently selected from hydrogen, nitro, cyano, fluoro, chloro, bromo, methyl, ethyl, isopropyl, trifluoromethyl, fluoromethyl, methoxy and methoxycarbonyl.
  • Het-1 examples are 3,5-dimethylpyrazol-1-yl, 3,5-diisopropylpyrazol-1-yl, 3-methyl-5-isopropyl-pyrazol-1-yl, 3-isopropyl-5-methyl-pyrazole 1 -yl, 3-ethyl-5-methyl-pyrazol-1-yl, 3,4,5-trimethyl-pyrazol-1-yl, 3-chloro-pyrazol-1-yl, 3-methyl-pyrazole-1 yl, 3-methyl-4-chloro-pyrazol-1-yl, 3-trifluoromethylpyrazol-1-yl, 3-trifluoromethyl-5-methoxypyrazol-1-yl, 3-trifluoromethyl-5-methyl-pyrazole 1-yl, 3-methyl-5-methoxypyrazol-1-yl, 3,5-dichloro-4-methyl-pyrazol-1-yl, 3,5-dimethyl-4-chloro-pyrazol-1-yl, 3, 5-Ditrifluoromethyl
  • Het-2 are 1, 3-dimethylpyrazol-5-yl and 1-methyl-3-trifluoromethylpyrazol-5-yl.
  • Het-3 are 1, 5-dimethylpyrazol-3-yl and 1-methyl-5-methoxypyrazol-3-yl.
  • Het-4 examples include 1, 3-dimethylpyrazol-4-yl, 1, 5-dimethylpyrazol-4-yl, 1, 3,5-trimethylpyrazol-4-yl, 1-methyl-3-trifluoromethylpyrazol-4-yl and 1-methyl-5-trifluoromethylpyrazol-4-yl.
  • Het-5 are 1-methylpyrrol-2-yl, 1, 4-dimethylpyrrol-2-yl, 1-methyl-5-chloropyrrol-2-yl and 1-methyl-3,5- dichloropyrrole-2-yl.
  • Het-6 are 1, 4-dimethylpyrazol-3-yl and 1-methylpyrazol-3-yl.
  • Het-7 examples include thiazol-4-yl, 2-methylthiazol-4-yl, 2-methyl-5-bromothiazol-4-yl, 2-methyl-5-chlorothiazol-4-yl and 2,5-dichloro-thiazol-4-yl.
  • Het-8 is thiazol-2-yl.
  • Het-9 is thiazol-5-yl.
  • Het-10 examples include 3-methyl-isothiazol-4-yl and 3-methyl-5-chloro-isothiazol-4-yl.
  • An example of Het-1 1 is isothiazol-3-yl.
  • het-12 is isothiazol-5-yl.
  • het-13 examples include isoxazol-4-yl, 3,5-dimethylisoxazol-4-yl, 3-methylisoxazole and 3-chloro-isoxazol-4-yl,
  • Het-14 is isoxazol-3-yl.
  • Het-15 is isoxazol-5-yl.
  • Het-16 examples include oxazol-4-yl, 2-methyl-oxazol-4-yl and 2,5-dimethyloxazol-4-yl,
  • Het-17 is oxazol-2-yl.
  • het-18 is oxazol-5-yl.
  • Het-19 examples include 4,5-dichloro-imidazol-1-yl and 4,5-dimethyl-imidazol-1-yl.
  • Het-20 is 1-methyl-imidazol-4-yl.
  • Het-21 is 1-methylimidazol-2-yl.
  • Het-22 is 1-methylimidazol-5-yl.
  • Examples of het-23 include 3-chloro-1, 2,4-triazol-1-yl, 3-fluoro-1, 2,4-triazol-1-yl, 3-bromo-1, 2,4-triazole 1 -yl, 3-trifluoromethyl-1, 2,4-triazol-1-yl, 3,5-dimethyl-1,2,4-triazol-1-yl, 3,5-dichloro-1, 2,4- triazol-1-yl, 3,5-dibromo-1, 2,4-triazol-1-yl, 3,5-difluoro-1, 2,4-triazol-1-yl and 3,5-ditrifluoromethyl-1, 2,4-triazol-1-yl.
  • Het-24 examples include 4,5-dimethyl-1,2,3-triazol-1-yl, 4,5-dichloro-1,2,3-triazol-1-yl, 4,5-dibromo-1, 2,3-triazol-1-yl, 4,5-difluoro-1,2,3-triazol-1-yl, 4,5-ditrifluoromethyl-1,2,3-triazol-1-yl, 5-methyl 1, 2,3-triazol-1-yl, 5-chloro-1, 2,3-triazol-1-yl, 5-fluoro-1, 2,3-triazol-1-yl, 5-bromo-1, 2,3-triazol-1-yl, 5-trifluoromethyl-1,2,3-triazol-1-yl.
  • Het-25 is 1,2,3-triazol-2-yl.
  • Het-26 is 1-methyl-1,2,4-triazol-5-yl.
  • Het-27 is 1-methyl-1,2,3-triazol-5-yl.
  • Het-28 is 2-methyl-1,2,3-triazol-4-yl.
  • Het-29 is 1-methyl-1,2,4-triazol-3-yl.
  • Het-30 is 1-methyl-1,2,3-triazol-4-yl.
  • Het-31 is 2-methyl-1,2,3-triazol-5-yl.
  • Y is thienyl which is unsubstituted or has 1, 2 or 3 substituents L. Accordingly, Y represents one of the following residues Het-32 or Het-33, in which # denotes the attachment site and L 1 , L 2 , and L 3 independently of one another have the meanings given above for the formulas Het-1 to Het-31.
  • Het-32 examples are 2-thienyl, 5-methylthiophene-2-yl, 5-chlorothiophene-2-yl, 5-bromothiophene-2-yl, 3,5-dichlorothiophene-2-yl, 3,4,5- Trichlorothiophen-2-yl and 5-bromothiophen-2-yl.
  • Het-33 examples are 3-thienyl, 2-methylthiophen-3-yl, 2,5-dichlorothiophene-3-yl, 2,4,5-trichloro-thiophen-3-yl and 2,5-dibromothiophene-3 yl.
  • a further embodiment of the invention relates to compounds of the formula I in which Y is 1, 2,3-triazolyl or 1,2,4-triazolyl, where Y may have two identical or different substituents L.
  • Preferred embodiments of this Y are 3,5-dimethyl-1, 2,4-triazol-1-yl, 3,5-dichloro-1, 2,4-triazol-1-yl, 3,5-dibromo-1, 2,4-triazol-1-yl, 3,5-difluoro-1, 2,4-triazol-1-yl, 3,5-di- (trifluoromethyl) -1, 2,4-triazol-1-yl, 3-methyl-1, 2,4-triazol-1-yl, 3-chloro-1, 2,4-triazol-1-yl, 3-fluoro-1, 2,4-triazol-1-yl, 3 bromo-1, 2,4-triazol-1-yl, 3-trifluoromethyl-1,2,4-triazol-1-yl, 4,5-dimethyl-1,2,3-triazol-1-yl, 4, 5-dichloro-1,2,3-triazol-1-yl, 4,5-dibromo-1,2,3-triazol-1-y
  • Y is a five-membered nitrogen-containing heteroaromatic ring selected from pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl and isothiazolyl, wherein Y is unsubstituted or substituted with one, two, three or four same or different Substituents L.
  • Y here is unsubstituted or substituted pyrrolidinyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl or isothiazolyl.
  • Y is optionally substituted pyrrolyl, preferably via a ring carbon bonded to the backbone of formula I pyrrolyl, so 2-, or 3-pyrrolyl, more preferably 2-pyrrolyl.
  • the pyrrolyl radical has one, two, three or four substituents L.
  • Y is optionally substituted pyrazolyl, such as 1-, 3-, 4- or 5-pyrazolyl. Particularly preferred is Y 1-pyrazolyl or 4-pyrazolyl, more preferably 1-pyrazolyl.
  • the pyrazolyl radical preferably has one, two or three substituents L.
  • Y is optionally substituted imidazolyl, ie 1-, 2-, or 4-imidazolyl, more preferably 1- or 2-imidazolyl.
  • the imidazolyl radical has one, two or three substituents L.
  • # means in each case the point of attachment of the respective Y to the skeleton of the compounds of the formula I in each case independently of one another have the meanings given herein for L.
  • Y is pyrazolyl
  • a substitution pattern is selected from A-7, A-8, A-10, A-11, A-13, A-14, A-15, A-16 and A-19.
  • a substitution pattern is selected from A-21, A-22, A-23, A-24, A-25, A-26, A-27, A-28, A-29 and A-30. specifically selected from A-22, A-23, A-24, A-25 and A-27, A-28, and A-29.
  • Y is oxazolyl
  • a substitution pattern selected from A-36 and A-37 is particularly preferable.
  • a substitution pattern selected from A-39, A-40 and A-41 is particularly preferable.
  • Y is isothiazolyl
  • a substitution pattern selected from A-46 and A-47 is particularly preferable.
  • Y are: 1-methylpyrrol-2-yl, 1, 4-dimethylpyrrol-2-yl, 1-methyl-5-chloropyrrol-2-yl, 1-methyl-3,5-dichloropyrrol-2-yl, 3-methyl-5-isopropylpyrazol-1-yl, 3,5-dimethylpyrazol-1-yl, 3-isopropyl-5-methylpyrazol-1-yl, 3-ethyl-5-methylpyrazol-1-yl, 3 Methyl 5-methoxypyrazol-1-yl, 3,4,5-trimethylpyrazol-1-yl, 3,5-dimethyl-4-chloropyrazol-1-yl, 3-chloropyrazol-1-yl, 3,4-dichloro 5-trichloromethylpyrazol-1-yl, 3
  • Y is a five-membered heteroaryl group containing two nitrogen atoms as ring members, which is selected from 1, 2,3-thiadiazolyl, 1, 2,4-thiadiazolyl, 1, 3,4-thiadiazolyl, 1, 2 , 5-thiadiazolyl, 1, 2,4-oxadiazolyl, 1, 3,4-oxadiazolyl and 1, 2,5-oxadiazolyl, wherein Y may be unsubstituted or substituted with one or two L, wherein L is as defined above, or is preferably defined.
  • Y Special meanings for such Y are: 1, 3,4-thiadiazol-2-yl, 5-methyl- [1, 3,4] -thiadiazol-2-yl, 5-chloro- [1, 3,4] thiadiazol-2-yl, 5-bromo [1, 3,4] thiadiazol-2-yl, 1, 2,3-thiadiazol-4-yl, 5-methyl- [1,2,3] -thiadiazol-4-yl, 5-chloro [1,2,3] thiadiazol-4-yl, 5-bromo [1,2,3] thiadiazol-4-yl, 1,2,3-thiadiazole 5-yl, 4-methyl- [1,2,3] thiadiazol-5-yl, 4-chloro [1,2,3] thiadiazol-5-yl, 4-bromo [1, 2, 3] -thiadiazol-5-yl, 1, 2,4-thiadiazol-5-yl, 3-methyl [1, 2,4] thiadiazol-5-yl, 3-chloro [1, 2,4] thiadiazol-5-y
  • Y is a 6-membered heteroaryl radical containing one, two or three nitrogen atoms as ring members, which is unsubstituted or substituted by one, two or three substituents L.
  • substituents L include pyridinyl, pyrimidinyl, pyrazinyl , Pyridazinyl and triazinyl, in particular pyridinyl, pyrimidinyl and pyrazinyl, which are each unsubstituted or substituted by one, two, three or four independently selected L.
  • preference is given to compounds of the formula I in which Y is pyridinyl which, if appropriate, contains two, three or four substituents L.
  • Y is 2-pyridinyl, 3-pyridinyl or 4-pyridinyl, which is unsubstituted or contains one or two substituents L.
  • Y is furthermore preferably pyrimidinyl, in particular 2- or 4-pyrimidinyl, which is unsubstituted or contains one, two or three substituents L.
  • Y is furthermore preferably 2-pyrazinyl or 4-pyridazinyl which is unsubstituted or contains one, two or three substituents L.
  • Y 1, 3,5-triazinyl, which is unsubstituted or contains one, two or three substituents L.
  • substituents independently selected from fluoro, chloro, bromo, cyano, nitro, methyl, ethyl, methoxy, Methylthio, hydroximinomethyl, hydroxyiminoethyl, methoxyiminomethyl, methoxyiminoethyl and trifluoromethyl;
  • Specific examples of this embodiment of the invention are 3-fluoropyridin-2-yl, 3-chloropyridin-2-yl, 3-bromo
  • a further preferred embodiment of the invention relates to compounds of the formula I in which Y is 3-pyridazinyl which optionally has 1, 2 or 3 substituents L.
  • a further preferred embodiment of the invention relates to compounds of the formula I in which Y is 1,3,5-triazinyl which optionally has 1 or 2 substituents L.
  • L 1 , L 2 , L 3 and L 4 independently of one another are hydrogen or have one of the meanings given for L.
  • the radicals L 1 , L 2 , L 3 and L 4 are independently selected from hydrogen, halogen, nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, especially C 1 -C 2 -fluoroalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -alkoxycarbonyl.
  • L 1 , L 2 , L 3 and L 4 are independently selected from hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, isopropyl, trifluoromethyl, fluoromethyl, methoxy and methoxycarbonyl.
  • Het-34 examples are 2-pyridyl, 3-fluoro-pyridin-2-yl, 3-chloro-pyridin-2-yl, 3-bromo-2-pyridin-2-yl, 3-trifluoromethyl-pyridine-2-yl yl, 3-methylpyridin-2-yl, 3-ethyl-pyridin-2-yl 3,5-difluoropyridin-2-yl, 3,5-dichloro-pyridin-2-yl, 3,5-dibromo -pyridin-2-yl, 3-fluoro-5-trifluoromethyl-pyridin-2-yl, 3,5-dimethyl-pyridin-2-yl, 5-nitro-pyridin-2-yl, 5-cyano-pyridine-2 -yl, 5-methoxycarbonylpyridin-2-yl, 5-trifluoromethylpyridin-2-yl, 5-methylpyridin-2-yl, 4-methylpyridin-2-yl, and 6-methylpyridine 2-yl
  • Het-35 examples are 3-pyridyl, 2-chloro-pyridin-3-yl, 2-bromo-pyridin-2-yl, 2-methyl-pyridin-3-yl, 2,4-dichloro-pyridine-3 yl, 2,4-dibromopyridin-3-yl, 2,4-dimethyl-pyridin-3-yl, 2,4,6-trichloropyridin-3-yl, 2,4,6-tribromopyridin-3-yl, 2,4,6-trimethylpyridin-3-yl and 2,4-dichloro-6-methylpyridin-3-yl.
  • Het-36 examples include 4-pyridyl, 3-chloro-pyridin-4-yl, 3-bromo-pyridin-4-yl, 3-methyl-pyridin-4-yl, 3,5-dichloro-pyridine-4 yl, 3,5-dibromo-pyridin-4-yl and 3,5-dimethyl-pyridin-4-yl
  • Het-37 examples include 5-chloropyrimidin-4-yl, 5-fluoropyrimidin-4-yl, 5-fluoro-6-chloropyrimidin-4-yl, 2-methyl-6-trifluoromethyl-pyrimidin-4-yl, 2, 5-Dimethyl-6-trifluoromethyl-pyrimidin-4-yl, 5-methyl-6-trifluoromethyl-pyrimidin-4-yl, 6-trifluoromethyl-pyrimidin-4-yl, 2-methyl-5-fluoro-pyrimidine-4 yl, 2-methyl-5-chloro-pyrimidin-4-yl, 5-chloro-6-methyl-pyrimidin-4-yl, 5-chloro-6-ethyl-pyrimidin-4-yl, 5-chloro-6 isopropyl-pyrimidin-4-yl, 5-bromo-6-methyl-pyrimidin-4-yl, 5-fluoro-6-methyl-pyrimidin-4-yl, 5-fluoro-6-fluoromethyl-pyrimidin-4-y
  • het-38 examples include 4-methyl-pyrimidin-5-yl, 4,6-dimethyl-pyrimidin-5-yl, 2,4,6-trimethyl-pyrimidin-5-yl and 4-trifluoromethyl-6-methyl-pyrimidine 5-yl.
  • Het-39 examples include 4,6-dimethylpyrimidin-2-yl, 4,5,6-trimethylpyrimidin-2-yl, 4,6-ditrifluoromethyl-pyrimidin-2-yl and 4,6-dimethyl-5-chloro pyrimidin-2-yl.
  • Y is phenyl which is unsubstituted or substituted by one, two, three, four or five identical or different substituents L.
  • the phenyl group When the phenyl group is substituted, it preferably has one, two, three or four substituents L on, which can be the same or different.
  • L in each case independently has one of the meanings indicated above or given as being preferred for L.
  • Y is a substituted phenyl group A, wherein # is the point of attachment to the pyrazolopyrimidine skeleton and L 1 is fluorine, chlorine, CH 3 or CF 3 ;
  • L 2 , L 4 are independently hydrogen, fluorine or methoxy;
  • L 3 is hydrogen, fluorine, chlorine, CN, CH 3 , OCH 3 , NH 2 , NHCH 3 , N (CH 2 ) 2 , C (O) NH 2 ,
  • L 5 is hydrogen, fluorine, chlorine or CH 3 .
  • Y is one of the following substituents: 2-fluoro-6-chlorophenyl, 2,6-difluorophenyl, 2,6-dichlorophenyl, 2-fluoro-6-methylphenyl, 2,4, 6-trifluorophenyl, 2,6-difluoro-4-methoxyphenyl, 2-chloro-4-methoxyphenyl, pentafluorophenyl, 2-methyl-4-fluorophenyl, 2-trifluoromethylphenyl, 2-methoxy-6-fluorophenyl, 2-chlorophenyl, 2-fluorophenyl, 2,4-difluorophenyl, 2-fluoro-4-chlorophenyl, 2-chloro-4-fluorophenyl, 2-chloro-5-fluorophenyl, 2,3-difluorophenyl, 2,5-difluorophenyl, 2,3, 4-trifluorophenyl, 2-fluoro-6-chloroph
  • Y is phenyl which is unsubstituted or substituted with one, two or three substituents L independently selected from fluoro, chloro, bromo, cyano, nitro, formyl, methyl, ethyl, n -propyl, i -propyl, n Butyl, i-butyl, s-butyl, t-butyl, allyl, propargyl, methoxy, ethoxy, n-propoxy, i-propoxy, methylthio, ethylthio, n-propylthio, i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl , Ethylsulfonyl, allyloxy, propargyloxy, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluo
  • Y is phenyl which contains one, two or three substituents in the 2, 4 and / or 6-position which are independent are selected from the L recited herein as preferred, especially independently selected from fluoro and chloro.
  • Y is 2,4-, 2,5- or 2,6-disubstituted phenyl, 2-substituted phenyl or 2,4,6-trisubstituted phenyl, having substituents L which are independently selected from the group Fluorine, chlorine, bromine, cyano, nitro, OH, mercapto, methyl, ethyl, methoxy, methylthio, hydroxyiminomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl, carboxy and carboxymethyl.
  • Y is 2-trifluoromethylphenyl, 2-chloro-5-nitrophenyl or 2-chloro-4-methoxyphenyl.
  • L is preferably each independently selected from the preferred meanings given herein for L, and it may further be preferred that L is selected from halo, nitro, cyano, Ci-C 4 -AlkVl, d-C4 haloalkyl, in particular Ci-C2-fluoroalkyl, -C 4 -alkoxy, d-C4-alkoxycarbonyl, alkylaminocarbonyl, Ci-C4-alkylaminocarbonyl and di-Ci-C4-alkylaminocarbonyl, more preferably selected from nitro, cyano, fluorine, chlorine , Bromine, methyl, ethyl, isopropyl, trifluoromethyl, fluoromethyl, methoxy, methoxycarbonyl and aminocarbonyl.
  • Preferred L in the ortho position are fluorine, chlorine, bromine, C 1 -C 4 -alkyl, in particular methyl or ethyl, C 1 -C 2 -fluoroalkyl, such as trifluoromethyl, and C 1 -C 4 -alkoxy, in particular methoxy or ethoxy.
  • Y is C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 3 -C 10 -cycloalkyl or C 3 -C 10 -cycloalkenyl, where these radicals are one, two, three or four identical or different group R a and / or two substituents bonded to the same or adjacent atoms or ring atoms may be C 1 -C 6 -alkylene, oxy-C 2 -C 4 -alkylene or oxy-C 1 -C 3 -alkyleneoxy as defined herein.
  • Y is a C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl or C 2 -C 10 -alkynyl group which may each carry one, two, three or four identical or different groups R a .
  • such a group is represented by a five-, six-, seven-, eight-, nine- or ten-membered saturated, in particular five- or six-membered, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms - me from the group O, N and S, substituted.
  • Y is C 1 -C 10 -alkyl, preferably C 1 -C 6 -alkyl, in particular C 1 -C 4 -alkyl.
  • Y may each carry one, two, three or four identical or different groups R a , wherein R a is as defined herein and is preferably each independently selected from: halo, cyano, nitro, hydroxy, C 1 -C 6 -alkyl, d-Ce haloalkyl, C 3 -C 6 cycloalkyl, Ci-C 6 alkoxy, Ci-C 6 haloalkoxy, Ci-C 6 -
  • Ci-C 6 haloalkylthio Ci-C 6 alkylsulfinyl, Ci-C 6 haloalkylsulfinyl, Ci-C 6 - alkylsulfonyl, Ci-C 6 haloalkylsulfonyl, Ci-C 6 -alkylamino, di-Ci-C 6 Alkylamino, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyl, C 2 -C 6 -alkynyloxy and oxy-C 1 -C 4 -alkylenoxy.
  • R a is selected from halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C 4 alkoxy, Ci-C 4 - haloalkoxy, C 3 - C 6 cycloalkyl, C3-C6 halocycloalkyl, and -Si (Ci-C 6 alkyl).
  • Y is C 1 -C 10 -haloalkyl, preferably C 1 -C 6 -haloalkyl, in particular C 1 -C 4 -haloalkyl, which in each case contains one to five halogen atoms selected from fluorine, chlorine and bromine.
  • Y is an optionally substituted phenyl-Ci-Cio-alkyl group.
  • Another embodiment of alkyl groups in the Y position is the group Vd: where # denotes the bond to the pyrazolopyrimidine skeleton.
  • V in the group Vd is, for example, hydrogen; Halogen, such as fluorine, chlorine, bromine; C 1 -C 4 -alkyl, such as CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH (CHs) 2 ; C 1 -C 4 -haloalkyl, such as CH 2 Cl, CH 2 F, CH 2 Br, CHCH 2 , CHF 2 , CCI 3 , CF 3 , CH 2 CH 2 Cl, CH 2 CH 2 F, CH 2 CH 2 Br, CH 2 CHCl 2 , CH 2 CHF 2 , CH 2 CCI 3 , CH 2 CF 3 , CCI 2 CCI 3 , CF 2 CF 3 , CH 2 CH 2 CH 2 Cl, CH 2 CH 2 CH 2 F, CH 2 CH 2 CH 2 Br, CH 2 CH 2 CHF 2 , CH 2 CH 2 CHCl 2 , CF 2 CF 2 CF 3 , CH 2 CH 2 CH 2 Cl, CH 2 CH 2 CH 2 F, CH 2 CH 2 CH 2
  • CH 2 CH 2 CHBr 2 CH 2 CH 2 CCI 3 , CH 2 CH 2 CF 3 , CCI 2 CCI 2 CCI 3 , CF 2 CF 2 CF 3 , CH (CH 3 ) CH 2 Cl, CH (CH 3 ) CH 2 F, CH (CH 3 ) CH 2 Br; C 1 -C 4 -alkoxy, such as OCH 3 ; hydroxy; cyano; substituted C 1 -C 4 -alkyl, such as CH 2 OH, CH 2 CN, CH 2 OCH 3 , CH (CN) 2 , CH 2 CH 2 OCH 3 , CH 2 CH 2 CN, CH 2 CH (CN) 2 , CH 2 CH 2 OH, CH 2 CH 2 CH 2 OCH 3 , CH 2 CH 2 CH 2 OH, CH 2 CH 2 CH 2 CN, CH 2 CH 2 CH (CN) 2 .
  • V 2 in the group Vd is, for example, hydrogen or methyl, in particular hydrogen.
  • V 3 in the group Vd is, for example, C 3 -C 6 -alkyl, such as CH (CH 3 ) 2 ,
  • CH 2 CH 2 CH 2 CH 2 CH 3 CH (CH 3) CH 2 CH 3, CH 2 CH (CHs) 2, C (CHs) 3, CH 2 CH 2 CH 2 CH 3, CH (CH) CH 2 CH 2 CH 3 , CH 2 CH (CHs) CH 2 CH 3 , CH 2 CH 2 CH (CHS) 2 , CH (CH 3 ) CH (CHS) 2 , CH 2 CH 2 CH 2 CH 2 CHS, CH (CH 3 ) CH 2 CH 2 CH 2 CHS, CH 2 CH (CH 3 ) CH 2 CH 2 CHS, CH 2 CH (CH 3 ) CH 2 CHS, CH (CH 3 ) CH (CHS) CH 2 CH 3 , CH 2 CH (CH 2 CHS) 2 ; C 3 -C 4 -haloalkyl such as CH (CH 3 ) 2 CHCl 2 , CH (CH 3 ) CHF 2 , CH (CH 3 ) CHBr 2 , CH (CH 3 ) CCI 3 ,
  • Y is methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, s-butyl, tert-butyl, chloromethyl, trifluoromethyl or trifluoroisopropyl.
  • Y is not unsubstituted alkyl or CF 3 , in another embodiment Y is neither R a substituted nor unsubstituted alkyl.
  • Y is (C 2 -Cio) alkenyl, preferably (C 2 - Ce) alkenyl, in particular C 2 -C 4 -alkenyl.
  • Y may each carry one, two, three or four identical or different groups R a , wherein R a is as defined herein and is preferably each independently selected from: halogen, cyano, nitro, hydroxy, d Ce-alkyl, d-Ce-haloalkyl, C 3 -C 6 cycloalkyl, Ci-C 6 alkoxy, Ci-C 6 haloalkoxy, Ci-C 6 alkylthio, d-Ce-haloalkylthio, Ci-C 6 - alkylsulfinyl, Ci-C 6 haloalkylsulfinyl, Ci-C ⁇ alkylsulfonyl, Ci-C ⁇ -haloalkylsulfonyl, Ci-C ⁇ alkylamin
  • R a is selected from: halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 4 -alkyl, C6-cycloalkyl, Cs-C ⁇ -halocycloalkyl and -Si (Ci-C6-alkyl) 3.
  • YC is 2 -Cio-haloalkenyl, C 2 -C 6 haloalkenyl preferably, especially C3-C4-haloalkenyl, each containing from one to five, in particular one to three halogen atoms selected from fluorine, chlorine and bromine.
  • Preferred embodiments for alkenyl groups in position Y are the groups V.a
  • V 1 is hydrogen, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-cyanoalkyl,
  • V 1 C 1 -C 4 -hydroxyalkyl I; V 3 , V 4 C5-C8-alkyl or one of the groups mentioned at V 1 mean.
  • V 1 and V 2 independently represent, for example, hydrogen; Halogen, such as fluorine, chlorine, bromine; C 1 -C 4 -alkyl, such as CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH (CH 3 ) 2 ; C 1 -C 4 -haloalkyl, such as CH 2 Cl, CH 2 F, CH 2 Br, CHCH 2 , CHF 2 , CCI 3 , CF 3 , CH 2 CH 2 Cl, CH 2 CH 2 F, CH 2 CH 2 Br, CH 2 CHCl 2 , CH 2 CHF 2 , CH 2 CHBr 2 , CH 2 CCI 3 , CH 2 CF 3 , CCI 2 CCI 3 , CF 2 CF 3 , CH 2 CH 2 CH 2 Cl, CH 2 CH 2 CH 2 F, CH 2 CH 2 CH 2 Br, CH 2 CH 2 CHF 2 , CH 2 CH 2 CHCl 2 , CF 2 CF 2 CF 3 , CH 2 CH 2 CH 2 Cl, CH 2 CH 2 CH
  • V 3 and V 4 independently of one another are, for example, C 4 -C 6 -alkyl, such as CH 2 CH 2 CH 2 CH 3 , CH (CH 3 ) CH 2 CH 3 , CH 2 CH (CHs) 2 , C (CH) 3 , CH 2 CH 2 CH 2 CH 3 , CH (CH 3 ) CH 2 CH 2 CH 3 , CH 2 CH (CH 3 ) CH 2 CH 3 , CH 2 CH 2 CH (CHS) 2 , CH (CH 3 ) CH ( CHS) 2 , CH 2 CH 2 CH 2 CH 2 CHS, CH (CH 3 ) CH 2 CH 2 CH 2 CHS, CH 2 CH (CH 3 ) CH 2 CH 2 CHS, CH 2 CH (CH 3 ) CH 2 CH 2 CHS, CH 2 CH 2 CH (CH 3 ) CH 2 CHS, CH (CH 3 ) CH (CHS) CH 2 CH 3 , CH 2 CH (CH 2 CHS) 2 or one of the groups mentioned above at V.
  • Y represents allyl, but-2-en-1-
  • Y is (C 2 -C 10) -alkynyl, preferably (C 2 -C 6) -alkynyl.
  • Y may each carry one, two, three or four identical or different groups R a , wherein R a is as defined herein and is preferably each independently selected from: halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, Cr C4-alkoxy-Ci-C 4 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 -halocycloalkyl, Ci-C 4 -alkoxy -C 4 - haloalkoxy and -Si (Ci-C6 alkyl) 3 ,
  • a preferred embodiment for alkynyl groups in the Y position is the group V.c:
  • V 1 and V 2 independently of one another in the group Vc represent, for example, hydrogen, halogen, such as fluorine, chlorine, bromine; C 1 -C 4 -alkyl, such as CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH (CHs) 2 ; Halomethyl such as CH 2 Cl, CH 2 F, CH 2 Br, CHCH 2 , CHF 2 , CCI 3 , CF 3 ; CrC 4 alkoxy, such as OCH 3 ; hydroxy; cyano; substituted CrC 2 alkyl such as CH 2 OH, CH 2 CN, CH 2 OCH 3 , CH (CN) 2 , CH 2 CH 2 OCH 3 , CH 2 CH 2 CN, CH 2 CH (CN) 2 , CH 2 CH 2 OH.
  • halogen such as fluorine, chlorine, bromine
  • C 1 -C 4 -alkyl such as CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH (CHs) 2
  • V 3 in the group Vc is, for example, branched C 4 -C 6 -alkyl, such as CH (CH 3 ) CH 2 CH 3 , CH 2 CH (CH 2 ) 2 , C (CH 3 ) 3 , CH (CH 3 ) CH 2 CH 2 CHs, CH 2 CH (CH 3 ) CH 2 CH 3 , CH 2 CH 2 CH (CHs) 2 , CH (CH 3 ) CH (CHs) 2 , CH (CH 3 ) CH 2 CH 2 CHS, CH 2 CH (CH 3 ) CH 2 CH 2 CHS, CH 2 CH 2 CH (CH 3 ) CH 2 CHS, CH (CH 3 ) CH (CHS) CH 2 CH 3 , CH 2 CH (CH 2 CHs) 2 or one of above mentioned groups at V 1 .
  • Y is optionally substituted by R a , as defined herein, substituted C 3 -Cio-cycloalkyl, preferably optionally substituted Cs-Cs-cycloalkyl, in particular C 3 -C 7 -cycloalkyl.
  • Y may here in each case carry one, two, three or four identical or different groups R a , where R a is as defined herein and is preferably each independently selected from: halogen, cyano, nitro, hydroxy, C 1 -C 6 -alkyl, -haloalkyl, C 3 -C 6 cycloalkyl, -C 6 alkoxy, -C 6 - haloalkoxy, -C 6 -alkylthio, -C 6 haloalkylthio, CRCE alkylsulfinyl, CrC 6 - haloalkylsulfinyl, d-Ce-alkylsulfonyl, haloalkylsulfonyl CRCE , -C 6 alkylamino, di-CrC 6 alkylamino, C 2 -C 6 -alkenyl -alkyl, C 2 -C 6 alkenyloxy, C 2
  • R a is selected here from: halogen, cyano, -C 4 -alkyl, -C 4 haloalkyl, Ci-C4-alkoxy-CrC 4 alkyl, -C 4 alkoxy, -C 4 - haloalkoxy, C 3 -C 6 - Cycloalkyl, Cs-C 6 halocycloalkyl and -Si (C 1 -C 6 -alkyl) 3 .
  • Y is Cs-Cs-halocycloalkyl, preferred Example, C 3 -C6-Halogencycloalkyl, each containing one to three halogen atoms independently selected from fluorine, chlorine and bromine.
  • Y is C 3 -C 8 -cycloalkyl which is substituted by one, two or three methyl groups, preferably C 3 -C 6 -cycloalkyl.
  • V 1 in group Ve represents, for example, hydrogen or methyl
  • V 2 and V 3 in group Ve independently of one another denote, for example, hydrogen; cyano; Halogen, such as chlorine or bromine; C 1 -C 3 -alkyl, such as CH 3, CH 2 CH 3; CrC 3 - alkoxy, such as OCH 3 ; Halomethyl such as CH 2 Cl, CH 2 F, CH 2 Br, CHCH 2 , CHF 2 , CCI 3 , CF 3 .
  • V 2 and V 3 are the same.
  • V and V 2 in the groups Vf, Vg and Vh are preferably hydrogen.
  • Y is cyclopropyl, cyclopentyl, 2-methylcyclopentyl, cyclohexyl, 2-methylcyclohexyl or 2,2-dichlorocyclopropyl.
  • Y is an unsubstituted or substituted by R a, as defined above, substituted C3-Cio-cycloalkenyl, preferably C 3 - Cs-cycloalkenyl, in particular C5-C7-cycloalkenyl group.
  • Y may in each case carry one, two, three or four identical or different groups R a , where R a is as defined herein and is preferably each independently selected from halogen, cyano, nitro, hydroxy, C 1 -C 6 -alkyl, d-Ce-haloalkyl, C 3 -C 6 cycloalkyl, Ci-C 6 alkoxy, -C 6 - haloalkoxy, Ci-C 6 alkylthio, Ci-C 6 haloalkylthio, Ci-C 6 alkylsulfinyl, CrC 6 - haloalkylsulfinyl, Ci-C 6 alkylsulfonyl, Ci-C 6 haloalkylsulfonyl, Ci-C 6 -alkylamino, di-Ci-C 6 -alkylamino, C 2 -C 6 -alkenyl, C 2 -C 6 alkenyloxy, C -A
  • R a is selected here from: halogen, cyano, Ci-C 4 alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy, CrC 4 - haloalkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, and -Si (Ci-C 6 alkyl) 3, especially halogen and Ci-C 4 alkyl.
  • Y C3-C means 6 halocycloalkenyl, containing one, two or three halogen atoms independently selected from fluorine, chlorine and bromine.
  • Y by one, two or three methyl groups substituted Cs-Cs-cycloalkenyl, preferably C3-C 6 -alkenyl means -Cycloal.
  • the cycloalkenyl group preferably has one or two double bonds.
  • substituent Y examples are cyclopent-1-en-1-yl, cyclohex-1-en-1-yl, which may be substituted according to the invention by R a , as defined above.
  • Y is cyclopentylbenzene, 2-methylcyclopentenyl, 2-chlorocyclopentenyl, cyclohexenyl, 2-methylcyclohexenyl, 2-chlorocyclohexenyl or dichlorocyclohexenyl.
  • Z is NR 3 R 4 .
  • R 3 represents Ci -Ce-Al kyl, halo-dC 8 alkyl, C 2 -C 8 -alkenyl -alkyl, C 2 -C 8 haloalkenyl, C 2 -C 8 -alkyl kinyl, C 3 -C 8 haloalkynyl, C 3 -C 8 - cycloalkyl, C 3 -C 8 halocycloalkyl, C 3 -C 8 cycloalkyl-Ci-C 8 alkyl, C 6 -C 4 aryl, C 6 - Ci 4 - aryl-Ci-C 8 alkyl, five- or six-membered heteroaryl or five- or six-membered heteroaryl-Ci-C 8 alkyl.
  • R 4 is hydrogen, amino, C 1 -C 8 -alkylamino, di-C 1 -C 8 -alkylamino or one of the groups mentioned in R 3 .
  • the alkyl, alkenyl, alkynyl and cycloalkyl groups in R 3 and / or R 4 may in turn carry one, two or three identical or different groups R a , wherein R a is independently selected from halogen, cyano, C 1 -C 8 Alkoxy, C 1 -C 8 -alkyl, d- C 1 -haloalkoxy, C 1 -C 8 -alkylcarbonyl, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -alkylthio, tri-C 1 -C 6 -alkylsilyl, C 1 -C 8 -alkylamino and C 1 -C -alkylamino.
  • R 3 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -haloalkenyl, C 3 -C 8 -cycloalkyl, C 1 -C 5 -halocycloalkyl or C 3 -C 8 -cycloalkyl-C 1 -C 8 -alkyl.
  • R 4 is hydrogen, or one of the groups mentioned in R 3 .
  • Z is a group selected from ( ⁇ ) NHCH (CH 3 ) CH (CHS) 2 , (R) NHCH (CH 3 ) CH (CHS) 2 , (S) NHCH (CH 3 ) CH (CHS) 2 , ( ⁇ ) NHCH (CH 3 ) C (CHS) 3 , (R) NHCH (CH 3 ) C (CH 3 ) 3 , (S) NHCH (CH 3 ) C (CHS) 3 , ( ⁇ ) NHCH (CH 2 S) CH 2 CH 3 , (R) NHCH (CH 2 S) CH 2 CH 3 , (S) NHCH (CH 2 S) CH 2 CH 3 , ( ⁇ ) NHCH (CH 2 S) CH 2 CF 3 , (R) NHCH (CHS) CH 2 CF 3 and (S) NHCH (CHS) CH 2 CF 3 .
  • neither R 3 nor R 4 is hydrogen, where R 3 and R 4 are preferably selected independently of one another from C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 C6-haloalkenyl, Cs-C ⁇ cycloalkyl, and C 3 -C 6 halo-cycloalkyl, especially selected from Ci-C 6 alkyl, and Ci-C 6 haloalkyl.
  • R 3 is as previously defined or preferably defined and R 4 is hydrogen.
  • R a is in each case as defined above and preferably in each case independently halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy.
  • R 3 is straight-chain or branched, unsubstituted or substituted C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C 2 -C 5 -alkenyl, C 2 -C -alkynyl, C 1 -C 8 -cycloalkyl, unsubstituted or substituted phenyl or naphthyl or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S.
  • R a when attached to R 3 and / or R 4 is independently halogen, cyano, nitro, carboxyl, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 2 -C 5 -alkyl kenyl, C 2 -Cs -haloalkenyl, C 2 -Cs-alkynyl, Cs-Cs-haloalkynyl, C 1 -C 10 -alkadienyl, C 5 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, Cs-Cs-cyclo- alkenyl, Cs-Cio-bicycloalkyl, C 1 -C 8 -alkylaminothiocarbonyl, di-C 1 -C 8 -alkylaminothio-carbonyl, C 1 -C 6 -alkylene, -C (OO) -A
  • R 3 is in particular Ci -C 6 -alkyl, C 2 -C 6 -alkenyl -alkyl, C 2 -C 6 -alkyl kinyl, C 3 -C 6 -cycloalkyl, these radicals being 1, 2, 3, 4 or 5-fold may be substituted by halogen, Ci-C 6 alkyl or CrC 6 - haloalkyl.
  • component 1) As component 1)
  • Z 1 is hydrogen, fluorine or C 1 -C 4 -fluoroalkyl
  • Z 2 is hydrogen or fluorine, or Z 1 and Z 2 together form a double bond
  • q is 0 or 1;
  • R 14 is hydrogen or methyl. According to a specific embodiment of this embodiment, R 4 is hydrogen.
  • R 4 in the compounds of the formula I is hydrogen and R 3 is C 3 -C 6 -cycloalkyl which may be substituted by C 1 -C 4 -alkyl.
  • R 3 has one of the following meanings:
  • R 3 is C 1 -C 6 -haloalkyl (having one to five identical or different halogen atoms) or C 1 -C 6 -alkyl which has one to five halogen, cyano, hydroxyl, C 1 -C 4 -alkoxy, C 5 -C 6 -alkyl radicals.
  • R 3 is C 2 -C 8 haloalkenyl (having one to three same or different halogen atoms) or C 2 -C 8 alkenyl which is one to three halo, cyano, hydroxy, C 1 -C 4 alkoxy, C 3 -C 6 cycloalkyl -, SH, Ci-C4-alkylthio, amino, Ci-C4-alkylamino and / or di-Ci-C4-alkylamino groups can carry; or
  • R 3 is Cs-Cs haloalkynyl (having one to three same or different halogen atoms) or C 2 -C 8 alkynyl which is one to three halo, cyano, hydroxy, C 1 -C 4 alkoxy, Cs-C ⁇ cycloalkyl -, SH, Ci-C4-alkylthio, amino, Ci-C4-alkylamino and / or di-Ci-C4-alkylamino groups can carry; or
  • R 3 is C3-C8-halocycloalkyl (with one to three same or different halogen atoms), or Cs-Cs-cycloalkyl which may carry from one to three halogen and / or C1-C4 alkyl groups; or
  • R 3 is a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one, two, three or four heteroatoms from the group O, N and S, which is unsubstituted or substituted by one to four halogen, d-C 4- alkyl, cyano, nitro, hydroxy, C 3 -C 6 -cycloalkyl, Ci-C 4 -alkoxy and / or SH groups.
  • R 4 in these cases hydrogen, according to another embodiment, Ci-C ⁇ -alkyl.
  • R 3 and R 4 together with the nitrogen atom to which they are attached form a five- or six-membered saturated or partially unsaturated heterocycle containing one or two further heteroatoms from the group O, N and S as ring members may contain, wherein the heterocycle may carry one, two or three identical or different groups R a , as defined above.
  • each R a is independently selected from halo, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy.
  • R a is independently selected from d-Cs-alkyl and d-Cs-haloalkyl.
  • R 3 and R 4 together with the nitrogen atom to which they are attached form an unsubstituted or substituted by one, two or three identical or different fluorine, methyl and / or trifluoromethyl groups pyrrolidinyl, piperidinyl , Morpholinyl, thio morpholinyl, piperazinyl, 3,6-dihydro-1 (2H) pyridinyl or teterahydro-1 (2H) -pyridazinyl ring.
  • R 3 and R 4 together form -N (R ') (CH 2) 4, where zero, one, two or three hydrogen atoms are replaced by identical or different groups R ", where R" is independently Rmony is selected from methyl, ethyl, fluoro, chloro and trifluoromethyl, and wherein R 'is hydrogen or methyl; or R 3 and R 4 together form -NH (CH 2) 3, where zero, one, two or three hydrogen atoms are replaced by identical or different groups R '', where R '''is independently selected from methyl, ethyl, fluoro, Chlorine and trifluoromethyl.
  • R 3 and R 4 together with the nitrogen atom to which they are attached form a piperidinyl, morpholinyl or thiomorpholinyl ring which is optionally substituted by one, two or three identical or different groups R a , especially a piperidinyl ring.
  • the heterocycle formed is unsubstituted or substituted by one, two or three R a , wherein each R a is independently selected from halo, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl.
  • R 3 and R 4 together with the nitrogen atom to which they are attached are a 4-methylpiperidine ring, a 4-trifluoromethylpiperidine ring, a morpholine ring or a 3,4-dimethylpiperidine ring and especially a 4-methylpiperidine ring or form a 3,4-dimethylpiperidine ring.
  • R 3 and R 4 together with the nitrogen atom to which they are attached form a 5- or 6-membered heteroaryl which may be unsubstituted or substituted, preferably by 1, 2 or 3 groups R a .
  • the group NR 3 R 4 then forms a pyrazole ring which is optionally substituted in the manner described above and especially by 1 or 2 of the following radicals: halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, in particular by 2 methyl groups or two Trifluoromethyl groups in the 3,5-position.
  • compositions according to the invention contain at least one compound of the formula 1-1.1, as shown below.
  • compositions according to the invention contain at least one compound of the formula 1-1.2, as shown below.
  • compositions according to the invention comprise at least one compound of the formula I.2.1, as shown below. According to a further embodiment of the compositions according to the invention, these contain at least one compound of the formula I.2.2, as shown below.
  • compositions according to the invention comprise at least one compound of the formula 1-3.1, as shown below.
  • compositions according to the invention contain at least one compound of the formula I-3.2, as shown below.
  • compositions according to the invention comprise at least one compound of the formula 1-4.1, as shown below.
  • compositions according to the invention contain at least one compound of the formula I-4.2, as shown below.
  • compositions according to the invention contain at least one compound of the formula 1-5.1, as shown below.
  • compositions according to the invention comprise at least one compound of the formula I-5.2, as shown below.
  • the compounds I compiled in Tables 1 to 257 below are preferably used in the compositions according to the invention. Regardless of the combination in which they are mentioned, the groups mentioned in the tables for a substituent also individually represent a particularly preferred embodiment of the relevant substituent for a compound of the formula I.
  • Combination of Z and R 1 for a compound corresponds in each case to one row of Table B.
  • Combination of Z and R 1 for a compound corresponds in each case to one row of Table B.
  • Table 65 Compounds of the formula Ia.1, la.2, la.3, la.4, la.5, la.6, la.7, la.8, la.9, la.10, Ia.1 1,
  • Combination of Z and R 1 for a compound corresponds in each case to one row of Table B.
  • Table 82 Compounds of the formula Ia.1, La.2, La.3, La.4, Ia.5, La.6, La.7, La.8, La.9, Ia.10, Ia.11,
  • Combination of Z and R 1 for a compound corresponds in each case to one row of Table B.
  • Combination of Z and R 1 for a compound corresponds in each case to one row of Table B.
  • Combination of Z and R 1 for a compound corresponds in each case to one row of Table B.
  • Combination of Z and R 1 for a compound corresponds in each case to one row of Table B.
  • Combination of Z and R 1 for a compound corresponds in each case to one row of Table B.
  • Table 140 Compounds of the formulas Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1,
  • Table 141 Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1,
  • Combination of Z and R 1 for a compound corresponds in each case to one row of Table B.
  • Table 152 Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1,
  • Combination of Z and R 1 for a compound corresponds in each case to one row of Table B.
  • Combination of Z and R 1 for a compound corresponds in each case to one row of Table B.
  • Table 170 Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1,
  • Table 171 Compounds of the formula Ia.1, la.2, la.3, la.4, la.5, la.6, la.7, la.8, la.9, la.10, la.1 1,
  • Table 180 Compounds of the formula Ia.1, la.2, la.3, la.4, la.5, la.6, la.7, la.8, la.9, la.10, Ia.1 1,
  • Table 181 Compounds of the formula Ia.1, la.2, la.3, la.4, la.5, la.6, la.7, la.8, la.9, la.10, Ia.1 1,
  • Z and R 1 for a compound corresponds in each case to one row of Table B.
  • Table 201 Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1,
  • Table 205 Compounds of the formula Ia.1, La.2, La.3, La.4, La.5, La.6, La.7, Ia.8, Ia.9, Ia.10, Ia.1 1,
  • Combination of Z and R 1 for a compound corresponds in each case to one row of Table B.

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Abstract

L'invention concerne des compositions fongicides pour la lutte contre les champignons nuisibles phytopathogènes, comprenant, en quantité synergique, au moins un composé de formule (I) et au moins une substance active II sélectionnée dans les groupes (A) à (F), comme défini dans les revendications ou encore la description.
PCT/EP2007/061083 2006-10-18 2007-10-17 Compositions fongicides WO2008046856A2 (fr)

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* Cited by examiner, † Cited by third party
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CN103444736A (zh) * 2013-09-29 2013-12-18 江苏省绿盾植保农药实验有限公司 一种含有多抗霉素和苯酰菌胺的杀菌剂组合物
CN103798249A (zh) * 2014-02-24 2014-05-21 姚卫平 一种预防和治疗水稻穗颈瘟病的田间桶混增效药肥及其喷施方法
CN106259358A (zh) * 2016-08-18 2017-01-04 江西禾益化工股份有限公司 一种含有二氰蒽醌的复配杀菌组合物
US10800782B2 (en) 2016-08-31 2020-10-13 Agios Pharmaceutical, Inc. Inhibitors of cellular metabolic processes
CN114751910A (zh) * 2022-05-17 2022-07-15 重庆文理学院 一种可诱导细胞巨泡式死亡的化合物及其制备方法和应用

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004000844A1 (fr) * 2002-05-29 2003-12-31 Bayer Cropscience Aktiengesellschaft Pyrazolopyrimidines
WO2004106341A1 (fr) * 2003-06-03 2004-12-09 Basf Aktiengesellschaft Pyrazolopyrimidines substituees, procedes pour leur production, leur utilisation pour lutter contre des champignons nuisibles, et agents contenant lesdites pyrazolopyrimidines
WO2005000851A1 (fr) * 2003-06-27 2005-01-06 Bayer Cropscience Aktiengesellschaft Pyrazolopyrimidines
WO2005056555A1 (fr) * 2003-12-10 2005-06-23 Bayer Cropscience Aktiengesellschaft Pyrazolopyrimidines
WO2005056556A1 (fr) * 2003-12-10 2005-06-23 Bayer Cropscience Aktiengesellschaft Pyrazolopyrimidines
WO2005056558A1 (fr) * 2003-12-10 2005-06-23 Bayer Cropscience Aktiengesellschaft Pyrazolopyrimidines utilisees comme agents fongicides
WO2005082907A2 (fr) * 2004-02-20 2005-09-09 Bayer Cropscience Ag Pyrazolopyrimidines
WO2007012598A1 (fr) * 2005-07-27 2007-02-01 Basf Aktiengesellschaft Melanges fongicides a base d'azolopyrimidinylamines
WO2007101859A1 (fr) * 2006-03-07 2007-09-13 Basf Se Pyrazolopyrimidines substituées, procédés de production associés et leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004000844A1 (fr) * 2002-05-29 2003-12-31 Bayer Cropscience Aktiengesellschaft Pyrazolopyrimidines
WO2004106341A1 (fr) * 2003-06-03 2004-12-09 Basf Aktiengesellschaft Pyrazolopyrimidines substituees, procedes pour leur production, leur utilisation pour lutter contre des champignons nuisibles, et agents contenant lesdites pyrazolopyrimidines
WO2005000851A1 (fr) * 2003-06-27 2005-01-06 Bayer Cropscience Aktiengesellschaft Pyrazolopyrimidines
WO2005056555A1 (fr) * 2003-12-10 2005-06-23 Bayer Cropscience Aktiengesellschaft Pyrazolopyrimidines
WO2005056556A1 (fr) * 2003-12-10 2005-06-23 Bayer Cropscience Aktiengesellschaft Pyrazolopyrimidines
WO2005056558A1 (fr) * 2003-12-10 2005-06-23 Bayer Cropscience Aktiengesellschaft Pyrazolopyrimidines utilisees comme agents fongicides
WO2005082907A2 (fr) * 2004-02-20 2005-09-09 Bayer Cropscience Ag Pyrazolopyrimidines
WO2007012598A1 (fr) * 2005-07-27 2007-02-01 Basf Aktiengesellschaft Melanges fongicides a base d'azolopyrimidinylamines
WO2007101859A1 (fr) * 2006-03-07 2007-09-13 Basf Se Pyrazolopyrimidines substituées, procédés de production associés et leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant

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CN103444736B (zh) * 2013-09-29 2016-02-10 江苏省绿盾植保农药实验有限公司 一种含有多抗霉素和苯酰菌胺的杀菌剂组合物
CN103798249A (zh) * 2014-02-24 2014-05-21 姚卫平 一种预防和治疗水稻穗颈瘟病的田间桶混增效药肥及其喷施方法
CN106259358A (zh) * 2016-08-18 2017-01-04 江西禾益化工股份有限公司 一种含有二氰蒽醌的复配杀菌组合物
US10800782B2 (en) 2016-08-31 2020-10-13 Agios Pharmaceutical, Inc. Inhibitors of cellular metabolic processes
US11325914B1 (en) 2016-08-31 2022-05-10 Servier Pharmaceuticals Llc Inhibitors of cellular metabolic processes
USRE49934E1 (en) 2016-08-31 2024-04-23 Servier Pharmaceuticals Llc Inhibitors of cellular metabolic processes
CN114751910A (zh) * 2022-05-17 2022-07-15 重庆文理学院 一种可诱导细胞巨泡式死亡的化合物及其制备方法和应用
CN114751910B (zh) * 2022-05-17 2023-02-24 重庆文理学院 一种可诱导细胞巨泡式死亡的化合物及其制备方法和应用

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