EP1791427A1 - (hetero)cyclylcarboxamide zur bekämpfung von schadpilzen - Google Patents
(hetero)cyclylcarboxamide zur bekämpfung von schadpilzenInfo
- Publication number
- EP1791427A1 EP1791427A1 EP05777428A EP05777428A EP1791427A1 EP 1791427 A1 EP1791427 A1 EP 1791427A1 EP 05777428 A EP05777428 A EP 05777428A EP 05777428 A EP05777428 A EP 05777428A EP 1791427 A1 EP1791427 A1 EP 1791427A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- phenyl
- alkyl
- halogen
- hydrogen
- alkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 125000005842 heteroatom Chemical group 0.000 title claims abstract description 27
- 244000053095 fungal pathogen Species 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 71
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 24
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- -1 C 2 -C 6 haloalkynyl Chemical group 0.000 claims description 393
- 229910052736 halogen Inorganic materials 0.000 claims description 84
- 229910052739 hydrogen Inorganic materials 0.000 claims description 84
- 239000001257 hydrogen Substances 0.000 claims description 82
- 150000002367 halogens Chemical class 0.000 claims description 64
- 150000002431 hydrogen Chemical class 0.000 claims description 56
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 41
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 33
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 22
- 241000233866 Fungi Species 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 229910052727 yttrium Inorganic materials 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 2
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 2
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000005347 halocycloalkyl group Chemical group 0.000 claims 1
- 244000000004 fungal plant pathogen Species 0.000 abstract description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 138
- 150000003254 radicals Chemical class 0.000 description 50
- 241000196324 Embryophyta Species 0.000 description 44
- 239000000460 chlorine Substances 0.000 description 31
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 30
- 229910052801 chlorine Inorganic materials 0.000 description 30
- 239000011737 fluorine Substances 0.000 description 28
- 229910052731 fluorine Inorganic materials 0.000 description 28
- 125000005843 halogen group Chemical group 0.000 description 25
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 24
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 24
- 229910052794 bromium Inorganic materials 0.000 description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 24
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 23
- 239000004480 active ingredient Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 206010061217 Infestation Diseases 0.000 description 17
- 239000000417 fungicide Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000013543 active substance Substances 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 241000209140 Triticum Species 0.000 description 8
- 235000021307 Triticum Nutrition 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 239000007900 aqueous suspension Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 125000001153 fluoro group Chemical group F* 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 230000000855 fungicidal effect Effects 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000004463 2,4-dimethyl-thiazol-5-yl group Chemical group CC=1SC(=C(N1)C)* 0.000 description 5
- 241001281803 Plasmopara viticola Species 0.000 description 5
- 239000004359 castor oil Substances 0.000 description 5
- 235000019438 castor oil Nutrition 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 239000006072 paste Substances 0.000 description 5
- 230000003032 phytopathogenic effect Effects 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 235000013311 vegetables Nutrition 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 4
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- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 150000003217 pyrazoles Chemical class 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
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- 239000000126 substance Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 239000004215 Carbon black (E152) Substances 0.000 description 3
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000005537 sulfoxonium group Chemical group 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- DKGYESBFCGKOJC-UHFFFAOYSA-N thiophen-3-amine Chemical class NC=1C=CSC=1 DKGYESBFCGKOJC-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical class CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000005500 uronium group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
- C07D231/40—Acylated on said nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Definitions
- the present invention relates to a method for controlling harmful fungi, i. Fungi which damage plants, and which are also referred to below as phytopathogenic fungi or phytopathogenic fungi.
- the invention additionally relates to the novel (hetero) cyclylcarboxamides and their salts, to the plant protection products containing them and to their use for controlling harmful fungi.
- Fungicidally active heterocyclylcarboxamides of biphenylamines have been described in numerous publications, e.g. in EP-A 545099, EP-A 589301, EP-A 591699, WO 97/08148, WO 00/09482, WO 01/42223, WO 01/49665, JP 2001/302505, WO 02/059086, WO 02/064562 WO 03/066609, WO 03/069995 and WO 03/070705.
- JP 08092223 describes fungicidally active heterocyclylcarboxanilides which carry a heteroaromatic radical on the phenyl ring.
- WO 00/09482 discloses trifluoromethylpyrrolecarboxamides of 3-aminothiophenes.
- WO 94/08999 describes herbicidally active 1- (1-H-pyrazol-3-yl) pyrazoles which may have an aminocarbonylphenyl radical in the 5-position.
- WO 2005/023761 describes benzoic acid amides of 1-phenylpyrazole amines, which, due to their action as cytokine inhibitors, are suitable for the treatment of inflammatory diseases.
- the present invention therefore relates to a method for controlling plant-pathogenic fungi, wherein the harmful fungi, their habitat or the plants, areas, materials or spaces to be kept free of them with a fungicidally effective amount of at least one (hetero) cyclylcarboxamids of the following defined general formula I and / or at least one agriculturally acceptable salt thereof.
- Radicals R b which are selected from halogen, nitro, CN, C r C 4 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C r C 4 alkoxy, -C 4 haloalkyl, Cs-Ce-halocycloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, and -C 4 -haloalkoxy; Y oxygen or sulfur;
- R 1 is H, OH, C r C 4 alkyl, C 3 -C 6 cycloalkyl, -C 4 alkoxy, -C 4 haloalkyl,
- R 2 , R 3 independently of one another are hydrogen, halogen, nitro, CN, C 1 -C 4 -alkyl,
- R 4 is halogen, nitro, CN, C r C 4 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 4 -alkyl keny I, C 2 -C kinyl 4 -alkyl, C 1 -C 4 -alkoxy, dC ⁇ haloalkyl, C 3 -C 6 -halocycloalkyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -haloalkynyl or dC 4 -haloalkoxy;
- R 5 is hydrogen, halogen, nitro, CN, OH, C r C 6 alkyl, C 3 -C 6 cycloalkyl,
- NR 9 R 10 -C (O) NR 9 R 10 , -C (S) NR 9 R 10 , phenyl or phenyl-C 1 -C 4 -alkyl, where the phenyl ring in the two last-mentioned radicals is optionally 1, 2, 3 or 4 may have the radicals mentioned under R 4 , wherein
- R 6 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl,
- R 7 C r C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl,
- -C 6 haloalkyl Cs-Ce-halocycloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, phenyl, phenyl-CrC 4 alkyl, phenyl-d -C 4 -haloalkyl, phenyl-C 2 - C 4 alkenyl, phenyl C 2 -C 4 haloalkenyl, phenyl C 2 -C 4 alkynyl,
- Phenyl-C 2 -C 4 -haloalkynyl where phenyl and the phenyl group in phenyl-C r C 4 -alkyl, phenyl-C r C 4 -haloalkyl, phenyl-C 2 -C 4 -alkenyl, phenyl-C 2 -C 4 -haloalkenyl, phenyl-C 2 -C 4 -alkynyl and phenyl-C 2 -C 4 -haloalkynyl may be unsubstituted or may carry one, two or three radicals R b ;
- R 8 is hydrogen, OH, C r C 4 alkyl, C r C 4 alkoxy, C 2 -C 4 alkenyl, C 2 -C kinyl 4 -alkyl, C 2 -C 4 alkenyloxy, C 2 -C 4 Alkynyloxy, C 1 -C 4
- R 9, R 10 denote independently hydrogen, C r C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 -alkynyl, where the hydrogen atoms in these groups may be substituted partially or completely by halogen,
- radicals R 4 and R 5 attached to adjacent carbon atoms may also stand for an alkylene chain having 3 to 5 members, in which 1 or 2 non-adjacent CH 2 groups may also be replaced by oxygen or sulfur and in which part or all of the hydrogens may be replaced by halogen;
- Ar is phenyl, naphthyl or a 5- or 6-membered heteroaromatic radical having 1, 2 or 3, among N, O, and S selected heteroatoms as ring members, which may optionally also carry a fused benzene ring,
- n 0, 1, 2, 3 or 4;
- the present invention also relates to the use of the (hetero) cyclylcarboxamides of the general formula I and their agriculturally useful salts as fungicides and crop protection agents containing them.
- Hetero cyclylcarboxamides of general formula I are known in part, e.g. from WO 94/08999, WO 2005/023761, US Pat. No. 6,548,512 and WO 98/28269, or are described in other documents as intermediates in the preparation of pharmaceutical active substances.
- the present invention also relates to (hetero) cyclylcarboxamide the general formula I and their agriculturally useful salts, wherein the Variables n, Y, Ar, R 1 , R 2 , R 3 , R 4 and R 5 have the meanings given here and A is an at least monounsaturated 5- or 6-membered heterocycle having 1, 2 or 3, under N, O, S 1 S (OO) and S (OO) 2 selected heteroatoms as ring members, which may be unsubstituted or may contain 1, 2 or 3 of the radicals R a as defined herein, excluding (hetero) cyclylcarboxamides of general formula I, wherein A is 1-phenylpyrazol-5-yl, 1-phenyl-3-methylpyrazol-5-yl, 1, 3-dimethyl-4-chloropyrazol-5-yl, 5-nitropyrazol-3-yl , 1-ethyl-3-methyl-4-nitropyrazol-5-yl, 5-methyl-4-nitropyra
- the invention further provides (hetero) cyclylcarboxamides of the general formula I ',
- R a1 represents C C_rAlkyl, Ci-C 4 alkoxy, C r C 4 haloalkyl, C r C 4 -haloalkoxy or halogen;
- R a2 represents hydrogen, halogen, nitro, CN, C r C 4 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl or Ci-C 4 alkoxy, wherein through the last 5 groups
- Halogen may be substituted
- R c is selected from hydrogen, halogen, nitro, CN, C 1 -C 4 -alkyl,
- 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 the pure enantiomers or diastereomers and mixtures thereof.
- Suitable compounds of the formula I also include all possible stereoisomers (cis / trans isomers) and mixtures thereof.
- Agriculturally useful salts are, above all, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the fungicidal activity of the compounds I.
- the cations used are in particular the ions of the alkali metals, preferably sodium and potassium, the alkaline earth metals, preferably calcium, magnesium and barium, and the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion, if desired, one to may carry four C 1 -C 4 -alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably Tn (C 1 -C 4 -alkyl) sulfonium and sulfoxonium
- Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of CrC 4 alkanoic acids, preferably formate, acetate, Propionate and butyrate. They can be formed by reaction of I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
- C n -C 1n indicates the particular possible number of carbon atoms in the respective substituent or substituent part. All carbon chains, ie all alkyl, haloalkyl, phenylalkyl, alkenyl, haloalkenyl, phenylalkenyl, alkynyl, haloalkynyl and phenylalkynyl parts can be straight-chain or branched.
- Halogenated substituents preferably carry one to five identical or different halogen atoms. The meaning halogen in each case represents fluorine, chlorine, bromine or iodine.
- C r C 4 -haloalkylthio etc .: for a C 1 -C 4 -alkyl radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, eg CH 2 F, CHF 2 , CF 3 , CH 2 CI, CH (CI) 2 , C (CI) 3 , chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2 Trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,
- C 1 -C 4 -alkyl is a C 1 -C 4 -alkyl radical as mentioned above, or is, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n Hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl,
- d-C ⁇ -haloalkyl for a dC 8 -alkyl radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for example, for one of the radicals mentioned under Ci-C 4 -haloalkyl or for
- 5-fluoro-1-pentyl 5-chloro-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5-trichloro-pentyl, undecafluoropentyl, 6-fluoro-1-hexyl, 6-chloro-1-hexyl, 6-bromo-1-hexyl, 6-iodo-1-hexyl, 6,6,6-trichloro-1-hexyl or dodecafluorohexyl;
- C 2 -C 4 -alkenyl unsaturated, straight-chain or branched hydrocarbon radical having 2 to 4 carbon atoms and a double bond in any position, for example ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butene-1 -yl, "1-buten-2-yl, 1-buten-3-yl, 2-buten-1-yl, 1-methyl-prop-1 -en-1-yl, 2-methyl-prop-1 - en-1 -yl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop-2-en-1-yl; C 2 -C 6 alkenyl for C 2 -C 4 alkenyl as mentioned above and z.
- n -penten-1-yl, n -penten-2-yl, n -penten-3-yl, n -penten-4-yl 1-methylbut-1-en-1-yl, 2-methyl-1-butene-1-yl, 3-methylbut-1-yn-1-yl, 1-methyl-but-2-yn-1-yl, 2-methyl-but-2-yl en-1 -yl, 3-methyl-but-2-en-1-yl, 1-methyl-but-3-en-1-yl, 2-methyl-but-3-en-1-yl, 3 Methyl-but-3-en-1-yl,
- C 2 -C 4 -haloalkenyl for unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4 carbon atoms and a double bond in any position (as mentioned above), wherein in these groups the hydrogen atoms partially or completely against halogen atoms as above especially fluorine, chlorine and bromine, are replaced, eg 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-trichloroallyl, 2,3-dichlorobut-2-one.
- C 2 -C 6 -haloalkenyl for C 2 -C 6 -alkenyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example for the radicals mentioned at C 2 -C 4 -haloalkenyl ;
- C 2 -C 6 -alkynyl for straight-chain or branched hydrocarbon groups having 2 to 6 carbon atoms and a triple bond in any position, for example ethynyl, prop-1-yn-1-yl, prop-2-yn-1-yl, n But-1-yn-1-yl, n-but-1-yn-3-yl, n-but-1-yn-4-yl, n-but-2-yn-1-yl, n-pent 1-yn-1-yl, n -pent-1-yn-3-yl, n -pent-1-yn-4-yl, n -pent-1-yn-5-yl, n-pent-2 in 1 -yl, n -pent-2-yn-4-yl, n -pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methyl-but 1-in-4-yl, n-hex-1-y
- C 2 -C 4 -haloalkynyl for unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4 carbon atoms and a triple bond in any position (as mentioned above), wherein in these groups the hydrogen atoms are partially or completely substituted by halogen atoms as above called, in particular fluorine, chlorine and bromine, may be replaced, eg
- C 2 -C 6 -haloalkynyl for C 2 -C 6 -alkynyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example for at
- C 1 -C 4 -alkoxy for OCH 3 , OC 2 H 5 , OCH 2 -C 2 H 5 , OCH (CH 3 ) 2 , n-butoxy, OCH (CHg) -C 2 H 5 , OCH 2 -CH (CHg) 2 or OC (CH 3) 3;
- Ci-C 4 -haloalkoxy a dC 4 alkoxy as mentioned above which is partially or fully substituted by, iodine of fluorine, chlorine, bromine and / or substituted, al ⁇ for example OCH 2 F, OCHF 2, OCF 3, OCH 2 CI, OCH (CI) 2 , OC (CI) 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-fluoropropoxy, 3-fluoropropoxy, 2 , 2-Difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH 2 -C 2 F 5, OCF 2 -C 2 F 5, 1 - (CH 2 F) -2-f luorethoxy, 1 - (CH 2 Cl) -2-chloroethoxy,
- C 3 -C 6 -cycloalkyl for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
- C 3 -C 6 -cycloalkyl which is optionally monosubstituted or polysubstituted by halogen: a C 3 -C 6 -cycloalkyl radical as mentioned above which is unsubstituted or partially or completely substituted by fluorine, chlorine, bromine and / or iodine is, so z.
- a C 3 -C 6 -cycloalkyl radical as mentioned above which is unsubstituted or partially or completely substituted by fluorine, chlorine, bromine and / or iodine is, so z.
- I-chlorocyclopropyl 1-fluorocyclopropyl, 2-chlorocyclopropyl, 2-fluorocyclopropyl, 4-chlorocyclohexyl, 4-bromocyclohexyl;
- Phenyl-C 1 -C 4 -alkyl for C 1 -C 4 -alkyl which is substituted by phenyl, for example benzyl, 1- or 2-phenylethyl, 1-, 2- or 3-phenylpropyl, it being possible for the phenyl part to be unsubstituted or 1, 2 or 3 radicals R b , where R b is selected from halogen, nitro, CN, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 4 -alkenyl,
- Phenyl-CrC 4 -haloalkyl for -C 4 haloalkyl, which is ated substitution by phenyl, where the phenyl moiety may be unsubstituted or may have 1, 2 or 3 radicals R b wear, wherein R b is selected from halogen, nitro, CN , C r C 4 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl and C 1 -C 4 -alkoxy, where the 5 last-named groups zu ⁇ by halogen may be substituted;
- Phenyl-C 2 -C 4 -alkenyl for C 2 -C 4 -alkenyl which is substituted by phenyl, for example for 1- or 2-phenylethenyl, 1-phenylprop-2-en-1-yl, 3-phenyl 1-propen-1-yl, 3-phenyl-2-propen-1-yl, 4-phenyl-1-buten-1-yl or 4-phenyl-2-buten-1-yl; wherein the phenyl moiety may be unsubstituted or may carry 1, 2 or 3 R b radicals, wherein R b is selected from halogen, nitro, CN, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 2 C 4 alkenyl, C 2 -C 4 alkynyl and C 1 -C 4 -alkoxy, the last 5 mentioned
- Groups may be substituted by halogen
- Phenyl-C 2 -C 4 -haloalkenyl for C 2 -C 4 -haloalkenyl which is substituted by phenyl, where the phenyl moiety may be unsubstituted or may carry 1, 2 or 3 radicals R b , where R b is selected from halogen , Nitro, CN,
- Phenyl-C 2 -C 4 -alkynyl for C 2 -C 4 -alkynyl which is substituted by phenyl, for example 1-phenyl-2-propyn-1-yl, 3-phenyl-1-propyn-1-yl , 3-phenyl-2-propyn-1-yl,
- Phenyl-C 2 -C 4 -haloalkynyl C 2 -C 4 haloalkynyl which is substituted by phenyl, where the phenyl moiety may be unsubstituted or may have 1, 2 or 3 radicals R b wear, wherein R b is selected from halogen , nitro, CN, Ci-C 4 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 4 -alkyl keny I, C 2 -C 4 alkynyl and C r C 4 -alkoxy, where the 5 last-mentioned Groups may be substituted by halogen;
- aromatic 5-membered radicals for example furyl, such as 2-furyl and 3-furyl, thienyl, such as 2-thienyl and 3-thienyl, pyrrolyl, such as 2-pyrrolyl and 3-pyrrolyl, isoxazolyl and 3-isoxazolyl, isoxazolyl and 5-isoxazolyl, isothiazolyl such as 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, pyrazolyl such as 3-pyrazolyl, 4-pyrazolyl and 5-pyrazolyl, oxazolyl such as 2-oxazolyl, 4-oxazolyl and 5-oxazolyl, thiazolyl
- 2-thiazolyl, 4-thiazolyl and 5-thiazolyl imidazolyl such as 2-imidazolyl and 4-imidazolyl, oxadiazolyl such as 1, 2,4-oxadiazol-3-yl, 1, 2,4-oxadiazol-5-yl and 1, 3,4-oxadiazol-2-yl, thiadiazolyl such as 1, 2,4-thiadiazol-3-yl, 1, 2,4-thiadiazol-5-yl and 1, 3,4-thiadiazol-2-yl, triazolyl as 1, 2,4-triazol-1-yl, 1, 2,4-triazol-3-yl and 1, 2,4-triazol-4-yl, 6-membered aromatic radicals, for example pyridinyl as
- X, X 1 are each independently N or CR C , wherein R c is H or has the meanings given for R b .
- R c is hydrogen
- R a4 is hydrogen, C r C 4 alkyl, -C 4 haloalkyl,
- CrC is 4 haloalkyl or phenyl which may be unsubstituted or 1, 2 or 3 radicals
- R b may carry wherein R a4 C r C 4 alkyl or C r C denotes in particular hydrogen, 4 haloalkyl;
- R a1 is hydrogen, dC 4 alkyl, C 1 -C 4 -alkoxy, dC 4 haloalkyl,
- C r C 4 haloalkoxy or halogen more preferably hydrogen, halogen, Ci-C 2 alkyl, C 1 -C 2 -alkoxy, C r C 2 fluoroalkoxy or C r C 2 fluoroalkyl;
- R a2 is hydrogen, halogen, nitro, CN 1 C r C 4 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 -alkoxy, wherein the last 5 groups may be substituted by halo gen; and
- R a3 is hydrogen, halogen, nitro, CN, C r C 4 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 -alkoxy, wherein the last 5 groups are may be substituted, particularly preferably hydrogen, fluorine, chlorine or C 1 -C 4 -AlkVl.
- R a1 is hydrogen, halogen, in particular fluorine or chlorine, C r C 4 -alkyl or dC 4 -haloalkyl. In particular, R a1 is different from hydrogen. More preferably, R a1 is halo, trifluoromethyl or methyl;
- R a2 is hydrogen
- R a3 is halogen, in particular fluorine or chlorine, or methyl.
- W preferably represents a group NR a4 , in which R a4 has the meanings mentioned above and in particular the meanings given as being preferred.
- R c is preferably hydrogen.
- X in formulas A-2, A-3 and A-4 is N.
- X in formula A-1 is especially CH.
- X.sup.1 is in particular N.
- radicals A-1 are in particular:
- R a1 , R a2 and R 0 have the abovementioned and in particular the preferred Be ⁇ interpretations.
- radicals A-2 are in particular:
- R a1 , R a3 , R a4 and R c have the abovementioned and in particular the preferred meanings.
- radicals A-3 are in particular:
- R a1 , R a3 and R 0 have the abovementioned and in particular the preferred Be ⁇ interpretations.
- radicals A-4 are in particular:
- R a1 , R a3 and R c have the abovementioned and in particular the preferred Be ⁇ interpretations.
- A-5 are in particular:
- A-6 are in particular:
- R a1 , R a2 and R c have the abovementioned and in particular the preferred Be ⁇ interpretations.
- radicals A examples include 2-chlorophenyl, 2-trifluoromethyl-phenyl, 2-difluoromethyl-phenyl, 2-methyl-phenyl, 2-chloro-pyridin-3-yl, 2-trifluoromethyl-pyridin-3-yl, 2 Difluoromethylpyridin-3-yl, 2-methylpyridin-3-yl,
- 2-trifluoromethyl-thiophen-3-yl 5-methyl-2-trifluoromethyl-thiophen-3-yl, 2-methyl-thiophen-3-yl, 2,5-dimethyl-thiophen-3-yl, 3-trifluoromethyl- thiophen-2-yl, 3-methyl-thiophen-2-yl, 3,5-dimethyl-thiophen-2-yl, 5-methyl-3-trifluoromethyl-thiophen-2-yl, 2-trifluoromethyl-furan-3 yl, 5-Methyl-2-trifluoromethyl-furan-3-yl, 2-methyl-furan-3-yl, 2,5-dimethyl-furan-3-yl, ⁇ -methyl- ⁇ , -dihydro-ti ⁇ oxathiin -S-yl ⁇ -methyl- ⁇ . ⁇ -dihydro ⁇ H-thiopyran-S-yl.
- A particularly preferably represents a radical A-1a, A-2a or A-3a,
- R a1 , R a2 , R a3 and R a4 have the abovementioned meanings and in particular the preferred meanings.
- Radicals A-1 a with R a1 are preferably hydrogen, halogen, C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy, C 1 -C 2 -fluoroalkoxy or C 1 -C 2 -fluoroalkyl; in particular hydrogen, chlorine, bromine, fluorine, methyl, ethyl, methoxy, trifluoromethyl, difluoromethyl, trifluoromethoxy or difluoromethoxy, most preferably fluorine, bromine, chlorine, methyl or trifluoromethyl, and especially chlorine; with R a2 is hydrogen, halogen, nitro, CN, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 4 -alkynyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy, where the last-mentioned groups can be substituted by halogen,
- radicals A-2a with: R a1 is hydrogen, halogen, C 1 -C 2 -alkyl,
- R a3 is hydrogen, halogen, nitro, CN, C r C 4 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 -alkoxy, where the last five groups can be substituted by halogen, preferably hydrogen, halogen and C 1 -C 4 -alkyl, in particular halogen, hydrogen; and especially hydrogen; and R a4 is hydrogen, -C 4 alkyl,
- R a1 is hydrogen, halogen, -C 2 alkyl, C 1 -C 2 -alkoxy, -C 2 fluoroalkoxy or -C 2 fluoroalkyl, in particular hydrogen, chlorine, bromine, fluorine, methyl, ethyl , Methoxy, trifluoromethyl, difluoromethyl, trifluoromethoxy or difluoromethoxy, most preferably fluorine, bromine, chlorine, methyl or trifluoromethyl, especially trifluoromethyl;
- R a3 is hydrogen, halogen, nitro, CN, -C 4 alkyl, C 3 C 6 cycloalkyl, C 2 -C 4 - alkenyl, C 2 -C 4 alkynyl, C r C 4 -alkoxy, where the 5 last groups which may be substituted by halogen, preferably hydrogen, halogen or C 1 -C 4 -alkyl, in particular hydrogen, methyl
- R 1 is hydrogen, OH, C 1 -C 4 -alkyl, in particular H, OH or methyl and particularly preferably hydrogen;
- R 2 is hydrogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, nitro, cyano or halogen; particularly preferably hydrogen, methyl, ethyl, CF 3 , nitro, cyano or halogen;
- R 3 is hydrogen, C 1 -C 4 -alkyl, Ci-C 4 haloalkyl, nitro, cyano or halogen; particularly preferably hydrogen, methyl, ethyl, CF 3 , nitro, cyano or halogen;
- R 4 is C r C 4 alkyl, C r C 4 alkoxy, -C 4 haloalkyl, C r C 4 haloalkoxy, nitro, Cya ⁇ no or halogen; more preferably -C 4 alkyl, C r C 4 alkoxy, nitro, cyano or halogen, and especially methyl, methoxy, fluorine, chlorine, bromine, nitro or Cya ⁇ no;
- n is 0 or 1, more preferably 0;
- R 5 is hydrogen, halogen, CN, NO 2 , NH 2 , C (O) NH 2 , C (S) NH 2 , C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, C 1 -C 6 -haloalkyl, C r C 4 alkoxy, -C 4 -haloalkoxy, C 3 -C 6 cycloalkyl, Cs-C ⁇ -halocycloalkyl, Ci -C kylcarbonyl 4 -alkyl, C r C 4 alkoxycarbonyl, -C 4 alkylamino, di-C 1 -C 4 alkylamino, C r C 4 alkylthio,
- Ar phenyl, a six-membered heteroaromatic compound having 1 or 2 nitrogen atoms, such as 2-, 3- or 4-pyridinyl, 2-, 4- or 5-pyrimidinyl, 2- or 3-pyrazinyl or 3- or 4-pyridazinyl or a five-membered heteroaromatic with a nitrogen atom and optionally another heteroatom selected from O, S and N, such as 3-, 4- or 5-pyrazolyl, 2-, 4- or 5-imidazolyl, 2-, 4- or 5-oxazolyl, 3-, 4 - or 5-isoxazolyl, 2-, 4- or 5-thiazolyl, 3-, 4- or 5-isothiazolyl, 2- or 3-furyl, 2- or 3-thienyl, or 2- or 3-pyrrolyl.
- Ar is phenyl, 2-, 3- or 4-pyridinyl, 2-, 4- or 5-pyrimidinyl and especially phenyl.
- R b , R 6 , R 7 , R 8 , R 9 and R 10 preferably have the following meanings:
- R b is halogen, nitro, CN, C r C 4 alkyl, especially methyl, C 1 -C 4 -alkoxy, especially methoxy,
- R 6 is hydrogen, -C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 cycloalkyl,
- R 7 C r C 6 alkyl, -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 4- alkynyl, C 3 -C 4 -haloalkynyl, phenyl-dC 2 -alkyl or phenyl, where phenyl may be unsubstituted in the two last-mentioned radicals or one or two halogen groups, especially fluorine or
- R 8 is hydrogen, OH, dC 4 alkyl or C r C 4 alkoxy; R 9 , R 10 independently of one another are H or C 1 -C 4 -alkyl.
- R a1 has the abovementioned, in particular the preferred meanings and is especially methyl, trifluoromethyl, chlorine, bromine or fluorine; R a2 has the meanings given above and is especially hydrogen;
- R a1 has the abovementioned meanings, in particular the preferred meanings, and is especially methyl, fluorine, chlorine, bromine or trifluoromethyl; R a3 has the abovementioned, in particular the preferred, meanings and is especially hydrogen;
- R a1 has the abovementioned meanings, in particular the preferred meanings, and especially methyl, fluorine, chlorine, Bromine or trifluoromethyl
- R a3 has the abovementioned meanings, in particular the preferred meanings, and is especially hydrogen
- R a1 has the abovementioned meanings, in particular the preferred meanings, and is especially methyl, fluorine, chlorine, bromine or trifluoromethyl;
- R a3 has the abovementioned, in particular the preferred, meanings and is especially hydrogen or methyl;
- R a1 has the abovementioned, in particular the preferred meanings and is especially methyl, fluorine, chlorine, bromine or trifluoromethyl; R a3 has the abovementioned, in particular the preferred, meanings and is especially hydrogen or methyl;
- R a1 has the abovementioned, in particular the preferred meanings and is especially methyl, fluorine, chlorine, bromine or trifluoromethyl
- R a3 has the abovementioned, in particular the preferred, meanings and is especially hydrogen or methyl;
- R a1 has the abovementioned, in particular the preferred meanings and especially for methyl, fluorine, chlorine, bromine or Trifluoromethyl
- R a3 has the abovementioned, in particular the preferred, meanings and is especially hydrogen or methyl
- R a2 has the meanings given above and is especially hydrogen;
- R a1 has the abovementioned meanings, in particular the preferred meanings, and especially represents methyl, fluorine, chlorine, bromine or trifluoromethyl.
- R 3 , R 4 , R 5 and n have the abovementioned meanings, and especially those in which:
- A is a radical A-1, A-2, A-3, A-4, A-5 or A-6, in particular A-1 a, A-2a or A-3a, and especially a radical which is selected from 2-chloropyridin-3-yl, 2-trifluoromethylpyridin-3-yl,
- R 3 is selected from H, methyl, trifluoromethyl, CN, NO 2 and halogen, especially H and trifluoromethyl;
- R 5 is hydrogen, halogen, CN, NO 2, NH 2, C (O) NH 2, C (S) NH 2, C r C 6 alkyl, C 2 -C 6 alkenyl, C r C 6 haloalkyl, dC 4 alkoxy, -C 4 -haloalkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, -C 4 alkylcarbonyl, -C 4 alkoxycarbonyl, C r C 4 alkylamino, di-C r C 4 - alkylamino, C 1 -C 4 -alkylthio,
- Table 7 Compounds of the general formulas IA and IB in which A is 1-methyl-3-difluoromethyl-5-fluoropyrazol-4-yl and R 3 , R 5 and (R 4 ) n for each individual compound correspond in each case to one row of Table A. ,
- the compounds of the general formulas IC, ID, IE, IF and IG are also suitable with regard to their use as fungicides and active compounds for combating pests,
- R 2 and R 3 have the abovementioned meanings and, among these, in particular those in which:
- A is a radical A-1, A-2, A-3, A-4, A-5 or A-6, in particular A-1a, A-2a or A-3a, and especially a radical selected is under
- 2-methyl-4-trifluoromethylthiazol-5-yl 2-methyl-4-difluoromethylthiazol-5-yl, 2,4-dimethylthiazol-5-yl, 2-methyl-5-trifluoromethylthiazol-4-yl, 2.5- Dimethylthiazol-4-yl, 2-methyl-4-trifluoromethyloxazol-5-yl, 2-trifluoromethylthiophen-3-yl, 5-methyl-2-trifluoromethylthiophen-3-yl, 3-trifluoromethylthiophene-2-yl and 2.5- dimethylfuran-3-yl;
- R 2 is H or CN
- R 3 is selected from H, methyl, trifluoromethyl, CN, NO 2 and halogen. Examples of these are the individual compounds of the formulas IC, ID, IE, IF and IG compiled in the following Tables 20 to 38, in which the variables R 2 and R 3 each have the meanings indicated in a row of Table B and the variable A is the has the meaning given in the respective table.
- Table 22 Compounds of the general formulas IC, ID, IE, IF and IG, in which A is 1-methyl-3-trifluoromethylpyrazol-4-yl and R 2 and R 3 for each individual compound correspond in each case to one row of Table B.
- R 2 and R 3 are each
- Table 29 Compounds of the general formulas IC, ID, IE, IF and IG, in which A is 2-methyl-4-trifluoromethylthiazol-5-yl and R 2 and R 3 for each individual compound correspond in each case to one row of Table B.
- the compounds of the formula I according to the invention can be prepared analogously to processes known per se from the prior art, for example according to Scheme 1 by reacting activated (heterocyclyl) carboxylic acid derivatives II with a 5-amino-1-arylpyrazole of the formula III [Houben-Weyl: "Methods of organ. Chemistry ", Georg Thieme Verlag, Stuttgart, New York 1985, Volume E5, pp. 941-1045.].
- Activated carboxylic acid derivatives II are, for example, halides, active esters, anhydrides, azides, for example chlorides, fluorides, bromides, para- Nitrophenyl esters, pentafluorophenyl esters, N-hydroxysuccinimide esters, hydroxybenzotriazole-1-yl esters
- the radicals A, Y, R 1 , R 2 , R 3 , R 4 , R 5 and n have the abovementioned meanings and esp ⁇ especially the meanings mentioned as preferred on and X is halogen, N 3 , a radical derived from an active ester, for example, para-nitrophenyloxy, pentafluorophenyloxy, Succinimidyloxy, benzotriazole-1-yxyxy or the radical of an aliphatic carboxylic acid such as Formyloxy, acetyloxy etc.
- the active compounds I can also be prepared, for example, by reaction of the acids IV with a 5-amino-1-arylpyrazole of the formula III in the presence of a coupling reagent according to Scheme 2.
- a coupling reagent according to Scheme 2.
- the radicals A, Y, R 1 , R 2 , R 3 , R 4 , R 5 and n have the abovementioned meanings and in particular the meanings mentioned as being preferred.
- Suitable coupling reagents are, for example:
- Carbodiimide-based coupling reagents e.g. N, N'-dicyclohexylcarbodiimide [J.C. Sheehan, G.P. Hess, J. Am. Chem. Soc. 1955, 77, 1067], N- (3-dimethylaminopropyl) -N'-ethyl-carbodiimide; Coupling reagents which form mixed anhydrides with carbonic esters, e.g. 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline [B. Belleau, G. Malek, J. Amer. Chem. Soc. 1968, 90, 1651.],
- Uronium-based coupling reagents or guanidinium N-oxide structure e.g. N, N, N ', N'-tetramethyl-O- (1H-benzotriazole-1-yl) -uronium hexafluorophosphate [R. Knorr, A. Trzeciak, W. Bannwarth, D. Gillessen, Tetrahedron Lett.
- Coupling reagents which form acid chlorides e.g. Phosphoric acid bis (2-oxo-oxazolidide) chloride [J. Diago-Mesequer, Synthesis 1980, 547.].
- reaction conditions required for this purpose are known to the person skilled in the art, for example from J. March, Advanced Organic Synthesis.
- the (heterocyclyl) carboxylic acids IV can be prepared by processes known from the literature and from these the (heterocyclyl) carboxylic acid derivatives II can be prepared by processes known from the literature [for example EP 0589313, EP 915868, US 4,877,441].
- the 5-amino-1-arylpyrazoles of the formula III are known or can be prepared, for example, according to the process shown in Scheme 4.
- the radicals R 2 , R 3 , R 4 , R 5 and n have the abovementioned meanings and in particular the meanings mentioned as being preferred.
- the 1-arylhydrazines of the formula V and the 2,3-dichloropropionitriles of the formula VI are known from the literature or can be prepared by processes known from the literature.
- V (V) (VI) (III)
- VI (III)
- the reaction of V with VI can be carried out analogously to processes known from the literature, as described, for example, by Dorn et al. ( J. Prakt. Chem. 321, (1979), p. 93).
- the compounds I are suitable as fungicides. They are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. Some of them are systemically active and can be used in plant protection as foliar and soil fungicides.
- Botrytis cinerea (gray mold) on strawberries, vegetables, ornamental plants and vines
- the compounds I are also suitable for controlling harmful fungi such as Pecilomyces variotii in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
- harmful fungi such as Pecilomyces variotii in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
- the compounds I are applied by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidal treated effective amount of the active ingredients.
- the application can be done both before and after the infection of the materials, plants or seeds by the fungi.
- the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90 wt .-% of active ingredient.
- the application rates in the application in crop protection depending on the nature of the desired effect between 0.01 and 2.0 kg of active ingredient per ha.
- the application rate of active ingredient depends on the type of application and the desired effect. Usual application rates in material protection are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of material treated.
- the compounds I can be converted into the usual formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
- the application form depends on the respective purpose; It should in any case ensure a fine and uniform distribution of the compound according to the invention.
- the formulations are prepared in a known manner, e.g. by stretching the active compound with solvents and / or excipients, if desired using emulsifiers and dispersants, in the case of water as diluent also other organic solvents as auxiliary solvents verwen ⁇ can be used.
- Suitable auxiliaries are essentially solvents such as aromatics (eg xylene), chlorinated aromatics (eg chlorobenzenes), paraffins (eg petroleum fractions), alcohols (eg methanol, butanol), ketones (eg cyclohexanone), Amines (eg, ethanolamine, dimethylformamide) and water; Carriers such as ground natural minerals (e.g., kaolins, clays, talc, chalk) and ground synthetic minerals (e.g., fumed silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates, and aryl sulfonates) and dispersants such as lignin-sulfite liquors and methyl cellulose.
- aromatics eg xylene
- chlorinated aromatics eg chlorobenzenes
- paraffins eg petroleum
- the surface-active substances are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali metal and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ether, condensation products of sulfonated naphthalene and Naphthalene derivatives with formal dehyd, condensation products of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated Isooctylphe- nol, octylphenol, nonylphenol, alkylphenol polyg
- mineral oil fractions of medium to high boiling point such as kerosine or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strong polar solvents, e.g. Dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, into consideration.
- mineral oil fractions of medium to high boiling point such as kerosine or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Benzene, tolu
- Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
- Granules e.g. Coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers.
- Solid carriers are e.g. Mineral earths, such as silica gel, silicas, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as eg Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as cereal flour, bark, wood and nutshell flour, cellulosic powder and other solid carriers.
- Mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, do
- the formulations generally contain between 0.01 and 95 wt .-%, preferably between 0.1 and 90 wt .-% of the active ingredient.
- the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
- V. 80 parts by weight of a compound of the invention are well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powdered silica gel and milled in a hammer mill (active substance content 80% by weight).
- IX 10 parts by weight of the compound of the invention in 63 parts by weight of cyclohexanone, 27 parts by weight of dispersant (for example, a mixture of 50 parts by weight of the adduct of 7 moles of ethylene oxide with 1 mole of isooctylphenol and 50 parts by weight of Adduct of 40 mol ethylene oxide with 1 molar castor oil).
- dispersant for example, a mixture of 50 parts by weight of the adduct of 7 moles of ethylene oxide with 1 mole of isooctylphenol and 50 parts by weight of Adduct of 40 mol ethylene oxide with 1 molar castor oil.
- the stock solution is then diluted to the desired concentration by dispensing into water, e.g. to a concentration in the range of 1 to 100 ppm.
- the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, litter, granules by spraying, misting, dusting, scattering or pouring.
- the forms of application depend entirely on the intended use; In any case, they should ensure as far as possible the finest distribution of the active compounds according to the invention.
- Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powders, oil dispersions) by addition of water.
- emulsions, pastes or oil dispersions the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetter, tackifier, dispersant or emulsifier.
- the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. Generally they are between 0.0001 and 10%. Frequently, even small amounts of active compound of compound I in the ready-to-use preparation are sufficient, e.g. 2 to 200 ppm. Likewise, ready-to-use preparations with active compound concentrations in the range of 0.01 to 1% are preferred.
- the active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
- UUV ultra-low-volume
- oils of various types, herbicides, fungicides, other pesticides, bactericides, possibly also just immediately before use are added.
- These funds can be used to finance the In accordance with the means in a weight ratio of 1: 10 to 10: 1 are added.
- the agents according to the invention may also be present in the form of application as fungicides together with other active substances, which may be e.g. with herbicides, insecticides, growth regulators, fungicides or with fertilizers.
- active substances which may be e.g. with herbicides, insecticides, growth regulators, fungicides or with fertilizers.
- Sulfur, dithiocarbamates and their derivatives such as ferridimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylene bisdithiocarbamate, manganese-zinc-ethylenediamine-bis-dithiocarbamate, tetramethylthiuram disulfides, ammonia complex of zinc (N, N-ethylene-bis-dithiocarbamate) , Ammonia complex of zinc (N, N'-propylene-bis-dithiocarbamate), zinc (N, N'-propylene-bis-dithiocarbamate), N, N'-polypropylene-bis (thiocarbamoyl) disulfide;
- Nitroderivatives such as dinitro (1-methylheptyl) -phenylcrotonate, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenyl-isopropylcarbonate, 5-nitro- isophthalate di-isopropyl;
- Heterocyclic substances such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6- (o-chloroanilino) -s-triazine, 0,0-diethyl-phthalimidophosphonothioate,
- Piperazine-1 4-diylbis-1 - (2,2,2-trichloroethyl) -formamide, 1- (3,4-dichloroanilino) -1-formylamino-2,2,2-trichloroethane, 2,6-dimethyl N-tridecyl-morpholine or its salts, 2,6-dimethyl-N-cycIododecyl-morpholine or its salts, N- [3- (p-tert-butylphenyl) -2-methylpropyl] -cis-2,6 -dimethyl-morpholine 1
- Strobilurins such as methyl E-methoxyimino [ ⁇ - (o-tolyloxy) o-tolyl] acetate, methyl E-2- ⁇ 2- [6- (2-cyanophenoxy) -pyrimidin-4-yloxy] -phenyl ⁇ -3-methoxyacrylate, methyl-E-methoxyimino [ ⁇ - (2-phenoxyphenyl)] - acetamide, methyl-E-methoxyimino [ ⁇ - (2,5-dimethylphenoxy) -o-tolyl] - acetamide,
- Anilinopyrimidines such as N- (4,6-dimethylpyrimidin-2-yl) -aniline, N- [4-methyl-6- (1-propynyl) -pyrimidin-2-yl] -aniline, N- [4-methyl- 6-cyclopropyl-pyrimidin-2-yl] -aniline, • phenylpyrroles such as 4- (2,2-difluoro-1,3-benzodioxol-4-yl) -pyrrole-3-carbonitrile,
- Cinnamic acid amides such as 3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) -acrylic acid morpholide,
- fungicides such as dodecylguanidine acetate, 3- [3- (3,5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl] glutarimide, hexachlorobenzene, DL-methyl-N- (2,6-dimethyl-phenyl) N-furoyl (2) alaninate,
- the active compounds were prepared as stock solution with 0.25% by weight of active compound in acetone or dimethyl sulfoxide (DMSO). To this solution was added 1% by weight of emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) and diluted with water according to the desired concentration.
- DMSO dimethyl sulfoxide
- the active compounds were prepared as a stock solution with 25 mg of active compound which was admixed with a mixture of acetone and / or DMSO and the emulsifier Uniperol® EL in a volume ratio of solvent to emulsifier of 99 to 1 ad 10 ml was filled up. Subsequently, it was filled up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the drug concentration given below.
- Leaves of pot fry were sprayed to drip point with aqueous suspension in the concentration of active compound given below.
- the undersurfaces of the leaves were inoculated with an aqueous sporangia suspension of Plasmopara viticola.
- the vines were first set up for 48 hours in a water vapor-saturated chamber at 24 0 C and then for 5 days in a greenhouse at temperatures between 20 and 30 0 C. After this time, the plants were again placed in a humid chamber for 16 hours to accelerate the sporangiopathic outbreak. Then the extent of infestation on the undersides of the leaves was visually determined.
- Example 3 the plants treated with 250 ppm of the active compound from Example 3, Example 4, Example 5, Example 6, Example 21, Example 23 or Example 30 of Table C showed a maximum of 10% infestation, while the untreated plants were 90 % were falling.
- Leaves of potted plants of the "golden queen" variety were sprayed to drip point with an aqueous suspension in the concentration of active compound specified below.
- the leaves were infected with an aqueous spore suspension of Altemaria solani in 2% biomalt solution having a density of 0.17 ⁇ 10 6 spores / ml.
- the plants were placed in a water vapor-saturated chamber at temperatures between 20 and 22 ° C. After 5 days, the disease on the untreated, but infected control plants had developed so strongly that the infestation could be determined visually in%.
- Leaves of pot vines were sprayed to drip point with aqueous suspension in the active ingredient concentration given below.
- the plants were placed in the greenhouse for 7 days after the spray coating had dried on. Thereafter, the undersurfaces of the leaves were inoculated with an aqueous sporangia suspension of Plasmopara viticola. Thereafter, the vines were first for 48 hours in a water vapor-saturated chamber at 24 0 C and then for 5 days in
- Paprika leaves of the cultivar "Neusiedler Ideal Elite" were, after 2 to 3 leaves had developed well, with an aqueous suspension in the below
- Leaves of potted wheat seedlings of the variety "Chancellor” were sprayed to drip point with aqueous suspension in the active ingredient concentration given below. Twenty-four hours after the spray coating had dried on, the leaves were dusted with the spores of wheat powdery mildew (Erysiphe graminis forma specialis tritici). Subsequently, the plants were placed in a greenhouse at temperatures between 20 and 24 0 C and 60 to 90% relative humidity. After 7 days, the extent of fungal attack was determined visually by the infestation of the leaf area.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004043046 | 2004-09-06 | ||
PCT/EP2005/009534 WO2006027198A1 (de) | 2004-09-06 | 2005-09-05 | (hetero)cyclylcarboxamide zur bekämpfung von schadpilzen |
Publications (1)
Publication Number | Publication Date |
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EP1791427A1 true EP1791427A1 (de) | 2007-06-06 |
Family
ID=35219274
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP05777428A Withdrawn EP1791427A1 (de) | 2004-09-06 | 2005-09-05 | (hetero)cyclylcarboxamide zur bekämpfung von schadpilzen |
Country Status (11)
Country | Link |
---|---|
US (1) | US20070275981A1 (zh) |
EP (1) | EP1791427A1 (zh) |
JP (1) | JP2008512358A (zh) |
CN (1) | CN101052301A (zh) |
AR (1) | AR050726A1 (zh) |
BR (1) | BRPI0514950A (zh) |
IL (1) | IL181418A0 (zh) |
PE (1) | PE20060502A1 (zh) |
TW (1) | TW200621152A (zh) |
UY (1) | UY29103A1 (zh) |
WO (1) | WO2006027198A1 (zh) |
Families Citing this family (4)
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CN101821239B (zh) | 2007-10-18 | 2014-01-01 | 组合化学工业株式会社 | 3-烷氧基-1-苯基吡唑衍生物及有害生物防除剂 |
AU2012326246B2 (en) | 2011-10-18 | 2015-09-17 | Fmc Corporation | Stable formulations containing fumed aluminum oxide |
AR102315A1 (es) * | 2014-04-02 | 2017-02-22 | Bayer Cropscience Ag | Derivados de pirazolil-nicotin(tio)amida sustituidos y su uso como fungicidas |
CN106699732A (zh) * | 2016-11-18 | 2017-05-24 | 安徽农业大学 | 一种吡唑烟酰胺类化合物的制备及其作为杀菌剂的应用 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0059169B1 (de) * | 1981-02-20 | 1984-03-28 | GRETAG Aktiengesellschaft | Vorrichtung zur Vorbereitung von Filmabschnitten mit Hinblick auf deren Durchlauf durch einen Kopierautomaten |
DE3609542A1 (de) * | 1986-03-21 | 1987-10-01 | Bayer Ag | 5-acylamino-pyrazol-derivate |
CA2081935C (en) * | 1991-11-22 | 2004-05-25 | Karl Eicken | Anilide derivatives and their use for combating botrytis |
DE4231517A1 (de) * | 1992-09-21 | 1994-03-24 | Basf Ag | Carbonsäureanilide, Verfahren zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen |
PL174304B1 (pl) * | 1992-10-12 | 1998-07-31 | Schering Ag | Podstawione pochodne pirazolu |
DE19632910C2 (de) * | 1996-08-16 | 2002-07-25 | Brose Fahrzeugteile | Verfahren zum berührungslosen Anfahren der unteren Anschlagsposition einer fremdkraftbetätigten Fensterscheibe eines Kraftfahrzeugs |
US6548512B1 (en) * | 1996-12-23 | 2003-04-15 | Bristol-Myers Squibb Pharma Company | Nitrogen containing heteroaromatics as factor Xa inhibitors |
DE19838708A1 (de) * | 1998-08-26 | 2000-03-02 | Bayer Ag | Verwendung von 5-Amino-pyrazol-Derivaten zur Bekämpfung von Mikroorganismen |
FR2803296B1 (fr) * | 1999-12-30 | 2002-02-15 | Rhodia Polyamide Intermediates | Procede de purification de lactames |
GB0101996D0 (en) * | 2001-01-25 | 2001-03-14 | Syngenta Participations Ag | Organtic compounds |
DE10107118A1 (de) * | 2001-02-14 | 2002-08-29 | Merck Patent Gmbh | Verfahren zur Herstellung von Bis(trifluormethyl)imido-Salzen |
DE10204390A1 (de) * | 2002-02-04 | 2003-08-14 | Bayer Cropscience Ag | Disubstituierte Thiazolylcarboxanilide |
DE10215292A1 (de) * | 2002-02-19 | 2003-08-28 | Bayer Cropscience Ag | Disubstitutierte Pyrazolylcarbocanilide |
US7186862B2 (en) * | 2002-02-23 | 2007-03-06 | Bayer Cropscience Ag | Microbicidal agents on the basis of biphenylbenzamide derivatives |
-
2005
- 2005-09-05 WO PCT/EP2005/009534 patent/WO2006027198A1/de active Application Filing
- 2005-09-05 EP EP05777428A patent/EP1791427A1/de not_active Withdrawn
- 2005-09-05 BR BRPI0514950-9A patent/BRPI0514950A/pt not_active IP Right Cessation
- 2005-09-05 PE PE2005001017A patent/PE20060502A1/es not_active Application Discontinuation
- 2005-09-05 JP JP2007528793A patent/JP2008512358A/ja not_active Withdrawn
- 2005-09-05 US US11/661,922 patent/US20070275981A1/en not_active Abandoned
- 2005-09-05 TW TW094130242A patent/TW200621152A/zh unknown
- 2005-09-05 AR ARP050103714A patent/AR050726A1/es unknown
- 2005-09-05 CN CNA200580037416XA patent/CN101052301A/zh active Pending
- 2005-09-06 UY UY29103A patent/UY29103A1/es unknown
-
2007
- 2007-02-19 IL IL181418A patent/IL181418A0/en unknown
Non-Patent Citations (1)
Title |
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See references of WO2006027198A1 * |
Also Published As
Publication number | Publication date |
---|---|
JP2008512358A (ja) | 2008-04-24 |
UY29103A1 (es) | 2006-04-28 |
AR050726A1 (es) | 2006-11-15 |
CN101052301A (zh) | 2007-10-10 |
IL181418A0 (en) | 2007-07-04 |
TW200621152A (en) | 2006-07-01 |
US20070275981A1 (en) | 2007-11-29 |
BRPI0514950A (pt) | 2008-07-01 |
PE20060502A1 (es) | 2006-07-18 |
WO2006027198A1 (de) | 2006-03-16 |
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