WO2003059065A1 - Ceto-enols cycliques substitues par un biphenyle - Google Patents
Ceto-enols cycliques substitues par un biphenyle Download PDFInfo
- Publication number
- WO2003059065A1 WO2003059065A1 PCT/EP2003/000026 EP0300026W WO03059065A1 WO 2003059065 A1 WO2003059065 A1 WO 2003059065A1 EP 0300026 W EP0300026 W EP 0300026W WO 03059065 A1 WO03059065 A1 WO 03059065A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- alkoxy
- optionally
- substituted
- methyl
- Prior art date
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title description 4
- 230000000855 fungicidal effect Effects 0.000 title description 4
- 125000004122 cyclic group Chemical group 0.000 title description 3
- 235000010290 biphenyl Nutrition 0.000 title description 2
- 239000004305 biphenyl Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 239000001257 hydrogen Substances 0.000 claims description 134
- 229910052739 hydrogen Inorganic materials 0.000 claims description 134
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 90
- 150000002431 hydrogen Chemical class 0.000 claims description 86
- 229910052760 oxygen Inorganic materials 0.000 claims description 84
- 229910052731 fluorine Inorganic materials 0.000 claims description 83
- 239000011737 fluorine Substances 0.000 claims description 83
- 229910052736 halogen Inorganic materials 0.000 claims description 83
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 82
- 239000001301 oxygen Substances 0.000 claims description 82
- 239000000460 chlorine Chemical group 0.000 claims description 81
- 229910052801 chlorine Inorganic materials 0.000 claims description 81
- 150000002367 halogens Chemical group 0.000 claims description 80
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 78
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 78
- 229910052717 sulfur Inorganic materials 0.000 claims description 78
- 239000011593 sulfur Substances 0.000 claims description 78
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
- -1 polyalkoxyalkyl Chemical group 0.000 claims description 69
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 49
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 49
- 125000001153 fluoro group Chemical group F* 0.000 claims description 45
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 44
- 229910052794 bromium Inorganic materials 0.000 claims description 44
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 44
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 43
- 229910052799 carbon Inorganic materials 0.000 claims description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 38
- 150000001721 carbon Chemical group 0.000 claims description 38
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 31
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 27
- 229920006395 saturated elastomer Chemical group 0.000 claims description 27
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 16
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 15
- 241000233866 Fungi Species 0.000 claims description 15
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 11
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
- 125000006413 ring segment Chemical group 0.000 claims description 10
- 229910052721 tungsten Inorganic materials 0.000 claims description 10
- 229910052727 yttrium Inorganic materials 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 229910021645 metal ion Inorganic materials 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- SQQWBSBBCSFQGC-JLHYYAGUSA-N ubiquinone-2 Chemical group COC1=C(OC)C(=O)C(C\C=C(/C)CCC=C(C)C)=C(C)C1=O SQQWBSBBCSFQGC-JLHYYAGUSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 101000652482 Homo sapiens TBC1 domain family member 8 Proteins 0.000 claims description 4
- 102100030302 TBC1 domain family member 8 Human genes 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 2
- 125000005108 alkenylthio group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims description 2
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical group COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000000417 fungicide Substances 0.000 abstract description 7
- 241000196324 Embryophyta Species 0.000 description 74
- 239000000203 mixture Substances 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 0 Cc1c(C(C(*(C2(*)*)O)=O)=C2OC(C*)=C)c(*)cc(*)c1N Chemical compound Cc1c(C(C(*(C2(*)*)O)=O)=C2OC(C*)=C)c(*)cc(*)c1N 0.000 description 15
- 238000012360 testing method Methods 0.000 description 14
- 239000003995 emulsifying agent Substances 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 230000001965 increasing effect Effects 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 244000005700 microbiome Species 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 230000001681 protective effect Effects 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 229920000742 Cotton Polymers 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 244000299507 Gossypium hirsutum Species 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 240000008042 Zea mays Species 0.000 description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
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- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
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- 229920000151 polyglycol Polymers 0.000 description 5
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- 230000009261 transgenic effect Effects 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
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- 125000002541 furyl group Chemical group 0.000 description 4
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- 125000003226 pyrazolyl group Chemical group 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
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- 125000000335 thiazolyl group Chemical group 0.000 description 4
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- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 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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- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
Definitions
- the present invention relates to known biphenyl-substituted cyclic ketoenols and their use as fungicides.
- biphenyl-substituted ketoenols have herbicidal, acaricidal and insecticidal properties: WO 99/48 869. Surprisingly, fungicidal properties have now also been found for the compounds described in WO 99/48869.
- X represents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, nitro or cyano
- Z represents optionally substituted aryl
- W and Y independently of one another represent hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, nitro or cyano, CKE for one of the groups
- halogen alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated, optionally substituted cycloalkyl, in which at least one ring atom is optionally replaced by a heteroatom, or in each case optionally by halogen, alkyl, haloalkyl, alkoxy, Halogenoalkoxy, cyano or nitro substituted aryl, arylalkyl or hetaryl,
- B represents hydrogen or alkyl, or A and B together with the carbon atom to which they are attached represent a saturated or unsaturated, optionally containing at least one heteroatom unsubstituted or substituted cycle,
- D represents hydrogen or an optionally substituted radical from the series
- a and D together with the atoms to which they are attached represent a saturated or unsaturated and optionally at least one heteroatom-containing cycle which is unsubstituted or substituted in the A, D part, or
- a and Q 1 together represent in each case alkanediyl or alkenediyl optionally substituted by optionally substituted alkyl, hydroxy, alkoxy, alkylthio, cycloalkyl, benzyloxy or aryl, or
- Q 1 represents hydrogen or alkyl
- OQ 4 > Q 5 and d 6 independently of one another represent hydrogen or alkyl
- Q 3 represents hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl, optionally substituted cycloalkyl (in which a methylene group is optionally replaced by oxygen or sulfur) or optionally substituted phenyl, or
- Q 3 and Q 4 together with the carbon atom to which they are attached represent a saturated or unsaturated, optionally a heteroatom-containing unsubstituted or substituted cycle, for hydrogen (a) or for one of the groups
- E represents a metal ion equivalent or an ammonium ion
- L represents oxygen or sulfur
- M oxygen or sulfur
- Rl for alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or cycloalkyl optionally substituted by halogen, alkyl or alkoxy, which may be interrupted by at least one heteroatom, in each case optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
- R2 represents in each case optionally substituted by halogen, alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or in each case optionally substituted cycloalkyl, phenyl or benzyl, ⁇ , R ⁇ and R ⁇ independently of one another each optionally by
- R6 and R ⁇ independently of one another for hydrogen, in each case optionally substituted by halogen alkyl, cycloalkyl, alkenyl, alkoxy,
- Alkoxyalkyl for optionally substituted phenyl, for optionally substituted benzyl, or together with the N atom to which they are attached, for an optionally substituted cycle interrupted by oxygen or sulfur.
- the compounds of the formula (I) can be present in different compositions as geometric and / or optical isomers or isomer mixtures, which can optionally be separated in a customary manner. Both the use of the pure isomers and that of the isomer mixtures as fungicides and compositions comprising them are the subject of the present invention. For the sake of simplicity, however, the following always refers to compounds of the formula (I), although both the pure compounds and, if appropriate, mixtures with different proportions of isomeric compounds are meant.
- A, B, D, G, Q 1 , Q 2 , Q 3 , Q 4 , Q 5 , Q 6 , W, X, Y and Z have the meaning given above.
- A, B, D, E, L, M, W, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given above.
- A, B, E, L, M, W, X, Y, Z, R 1 , R 2 , R 3 , R R5, R6 and R 7 have the meaning given above.
- the compounds of the formula (1-4) can exist in the two isomeric forms of the formulas (I-4-A) and (I-4-B),
- the compounds of the formulas (1-4-A) and (I-4-B) can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulas (I-4-A) and (I-4-B) can optionally be separated by physical methods, for example by chromatographic methods. For reasons of better clarity, only one of the possible isomers is listed below. This does not exclude that the compounds may optionally be in the form of the isomer mixtures or in the other isomeric form.
- A, B, Q ⁇ Q 2 , E, L, M, W, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R5, R6 and R 7 have the meanings given above.
- the compounds of the formula (1-5) can be present in the two isomeric forms of the formulas (I-5-A) or (I-5-B), which is indicated by the dashed line in the Formula (1-5) to be expressed:
- the compounds of the formulas (1-5 -A) or (1-5 -B) can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulas (I-5-A) and (I-5-B) can optionally be separated by physical methods, for example by chromatographic methods.
- A, B, E, L, M, Q 3 , Q 4 , Q 5 , Q 6 , W, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R5, R6 and R 7 die have the meanings given above.
- X preferably represents halogen, C ⁇ -C ⁇ - alkyl, Ci-COE-haloalkyl, C j -Cg- alkoxy, Ci-Cg-halogenoalkoxy, nitro or cyano,
- V 1 is preferably hydrogen, halogen, C r C 1 - alkyl, C r C 6 - alkoxy, C r C 6 alkylthio, C r C 6 -Alkylsulf ⁇ nyl, C r C 6 alkylsulfonyl, C r C 4 -halogen - alkyl, C ⁇ -C4-haloalkoxy, nitro, cyano or in each case optionally mono- or polysubstituted by halogen, C Cg-alkyl, C Cg-alkoxy, C1-C4 haloalkyl, C j -C haloalkoxy, nitro or cyano, phenyl, Phenoxy, phenoxy-C 1 -C 4 -alkyl, phenyl-C 1 -C 4 -alkoxy, phenylthio-C 1 -C 4 -alkyl or phenyl-C 1 -
- V 2 and V 3 are preferably each independently hydrogen, halogen, CJ-Cg alkyl, C j -Cg- alkoxy, C j -C 4 haloalkyl or haloalkoxy O j,
- W and Y are preferably independently of one another hydrogen, halogen, Cj-Cg-alkyl, C j- Cg-haloalkyl, C Cg-alkoxy, C j - -haloalkoxy, nitro or cyano,
- CKE preferably stands for one of the groups
- B preferably represents hydrogen or C ⁇ -C - alkyl
- A, B and the carbon atom to which they are attached preferably represent saturated C3-C j o-cycloalkyl or unsaturated C 5 -C ⁇ 0 cycloalkyl, in which optionally one ring member is replaced by oxygen or sulfur and which is optionally monosubstituted or disubstituted by C ⁇ -Cg-alkyl, C3-C10-cycloalkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy, Ci-Cg-alkylthio, halogen or phenyl are substituted or
- A, B and the carbon atom to which they are attached are preferably C3-C ⁇ -cycloalkyl, which is obtained by means of an alkylene diyl or optionally containing one or two oxygen and / or sulfur atoms which are not directly adjacent, or by an alkylenedioxyl or by an Alkylenedithioyl group is substituted, which forms a further five- to eight-membered ring with the carbon atom to which it is attached or
- A, B and the carbon atom to which they are attached are preferably C3-
- Cg-cycloalkyl or C5-Cg-cycloalkenyl in which two substituents together with the carbon atoms to which they are attached, for C2-C6-alkanediyl, C2 which are optionally substituted by C -C6-alkyl, Ci-Cg-alkoxy or halogen -C6-alkenediyl or C4-Cg-alkanedienediyl, in which a methylene group is optionally replaced by oxygen or sulfur, D preferably represents hydrogen, in each case optionally substituted by halogen -CC 2 -alkyl, C3-Cg-alkenyl, C3-Cg-alkynyl, C ⁇ -C ⁇ ) -alkoxy-C2-Cg-alkyl, poly-C ⁇ -Cg-alkoxy- C 2 -CG-alkyl, C ⁇ -C ⁇ 0 -alkylthio-C 2 -CG-alkyl, optionally substituted by
- Haloalkyl substituted C3-Cg-cycloalkyl in which a ring member is optionally replaced by oxygen or sulfur or in each case optionally by halogen, Cj-Cß-alkyl, Cj-Cg-haloalkyl, Cj-Cg-alkoxy, Ci-Cg-haloalkoxy, cyano or nitro substituted phenyl, hetaryl with 5 or 6 ring atoms (for example furanyl, imidazolyl, pyridyl, thiazolyl,
- a and D together preferably represent in each case optionally substituted C3-Cg-alkanediyl or C3-Cg-alkenediyl, in which a methylene group is optionally replaced by oxygen or sulfur and where the following are possible substituents: in each case Cj-Cg- which is optionally substituted by halogen Alkyl, C ⁇ -Cg alkoxy or another
- a and Q 1 together preferably represent in each case optionally one to three times, identical or different by halogen, by in each case optionally mono- to trisubstituted by identical or different halogen-substituted C ⁇ -Cio-alkyl or Cj-Cg-alkoxy-substituted C3-C6 alkanediyl or C4-COE-alkenediyl, also optionally substituted j by a C ⁇ alkanediyl group or by an oxygen atom is bridged or
- Q! preferably represents hydrogen or C 1 -C 4 alkyl
- Q 2 > O ⁇ Q 5 and Q 6 independently of one another preferably represent hydrogen or C r C 4 alkyl
- Q 3 preferably represents hydrogen, C r C 6 -alkyl, C r C 6 -alkoxy-C r C2-alkyl, C 1 -C 6 -alkylthio-C 1 -C 2 -alkyl, phenyl, optionally by C r C 4 - alkyl or C1-C4-alkoxy substituted C -Cg-cycloalkyl, in which a methylene group is optionally replaced by oxygen or sulfur or optionally by halogen, CJ-C4-alkyl, C1-C4-alkoxy, C j ⁇ -haloalkyl, C C2-haloalkoxy, cyano or nitro substituted phenyl or
- Q 3 and Q 4 together with the carbon atom to which they are attached, preferably represent a C3-C7 ring, optionally substituted by C1-C4-alkyl, C1-C4-alkoxy or C1-C2-haloalkyl, in which one Ring member is replaced by oxygen or sulfur,
- G preferably represents hydrogen (a) or one of the groups
- E represents a metal ion equivalent or an ammonium ion
- L represents oxygen or sulfur
- M oxygen or sulfur
- phenyl optionally substituted by halogen, cyano, nitro, Cj-Cg-alkyl, Cj-Cg-alkoxy, Ci-Cg-haloalkyl, Cj-Cg-haloalkoxy, Cj-Cg-alkylthio or C ⁇ - Cg-alkylsulfonyl,
- phenyl optionally substituted by halogen, nitro, cyano, Cj-Cg-alkyl, Ci-Cg-alkoxy, Cj-Cg-haloalkyl or Cj-Cg-haloalkoxy
- hetaryl optionally substituted by halogen or C 1 -C 6 -alkyl (for example pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl),
- phenoxy-Ci-Cg-alkyl optionally substituted by halogen or Cj-Cg-alkyl or for 5- or 6-membered hetaryloxy-Cj-Cg-alkyl optionally substituted by halogen, amino or Cj-Cg-alkyl (for example pyridyloxy-C ⁇ -C 6 -alkyl, pyrimidyloxy-C ⁇ -C 6 -alkyl or thiazolyloxy-C ⁇ - C 6 alkyl),
- R 2 preferably represents in each case optionally substituted by halogen C ⁇ -
- C20-alkyl C2-C20-alkenyl, -C-Cg-alkoxy-C2-Cg-alkyl, poly-Ci-Cg-alk-oxy-C2-Cg-alkyl,
- C3-Cg-cycloalkyl which is optionally substituted by halogen, Ci-Cg-alkyl or Cj-Cg-alkoxy or
- R 3 preferably represents optionally substituted by halogen Cj-Cg-alkyl or in each case optionally substituted by halogen, C ⁇ -Cg-alkyl, Ci-Cg-alkoxy, C ⁇ -C4-haloalkyl, C ⁇ -C4-haloalkoxy, cyano or nitro Phenyl or benzyl,
- R4 and R5 preferably independently of one another each represent optionally substituted by halogen C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino, di- (C 1 -C 6 -alkyl) amino, Cj-Cg-alkylthio, C2-Cg-alkenylthio, C3-C -cycloalkylthio or for each optionally by halogen, nitro, cyano, C1-C4- alkoxy, C ⁇ -C4-haloalkoxy, C ⁇ -C4-alkylthio, C1-C4-
- R "and R 7 are, independently of one another, preferably hydrogen, for each Ci-Cg-alkyl optionally substituted by halogen, C3-Cg-cycloalkyl, Ci-Cg-alkoxy, C3-Cg-alkenyl, -C-Cg-alkoxy- C ⁇ -Cg-alkyl, for counter phenyl optionally substituted by halogen, Ci-Cg-haloalkyl, C ⁇ -Cg-alkyl or Cj-Cg-alkoxy, benzyl optionally substituted by halogen, Cj-Cg-alkyl, Cj-Cg -haloalkyl or Cj-Cg-alkoxy or together to which they are bound to the nitrogen atom is substituted for a optionally substituted by C j ⁇ alkyl C3-Cg-alkylene radical in which optionally one carbon atom is replaced by oxygen or sulfur.
- halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
- X particularly preferably represents fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C1-C4-alkoxy, C 1 -C 4 -haloalkyl, Oj ⁇ -haloalkoxy, nitro or cyano,
- Z particularly preferably represents a radical
- V 1 particularly preferably represents hydrogen, fluorine, chlorine, bromine, C Cg-alkyl, Nitro, cyano or in each case optionally once or twice by fluorine, chlorine, bromine, -C 4 -alkyl, C j -C -alkoxy, C ] -C 2 -haloalkyl, Ci ⁇ -haloalkoxy,
- V 2 and V 3 are particularly preferably independently of one another hydrogen
- CKE particularly preferably stands for one of the groups
- B particularly preferably represents hydrogen or C j -C - alkyl or A, B and the carbon atom to which they are attached are particularly preferably saturated C -C -cycloalkyl, in which a ring member is optionally replaced by oxygen or sulfur and which is optionally mono- or disubstituted by Cj-Cg-alkyl, trifluoromethyl or Cj- Cg-alkoxy is substituted or
- A, B and the carbon atom to which they are bonded are particularly preferably C5-Cg-cycloalkyl or C5-Cg-cycloalkenyl, in which two substituents together with the carbon atoms to which they are bonded are each optionally Methyl, methoxy, fluorine, chlorine or bromine substituted C2-C4-alkanediyl, C2-C4-alkenediyl, in which a methylene group is optionally replaced by oxygen or sulfur or butadiene diyl
- D particularly preferably represents hydrogen, in each case optionally mono- to trisubstituted by fluorine or chlorine-substituted Cj-Cg-alkyl, C3 ⁇ Cg-alkenyl, Ci -C4-alkoxy-C2-C3-alkyl or -C-C4-alkylthio-C2- C3-alkyl, for optionally mono- to disubstituted by fluorine, chlorine, C1-C4-alkyl, C j - C4-alkoxy or -C-C2-haloalkyl, C3-C7-cycloalkyl, in which a methylene group is optionally replaced by oxygen or sulfur .
- a and D together particularly preferably represent optionally substituted C3-C5-alkanediyl in which a methylene group is substituted by oxygen or
- Sulfur can be replaced, methyl or methoxy being suitable as substituents or A and D (in the case of the compounds of the formula (II)) together with the atoms to which they are bonded represent one of the groups AD-1 to AD-10:
- a and Q 1 together are particularly preferably each C 1 -C 4 -alkyl or C C2-alkoxy which is optionally mono- to trisubstituted by fluorine or C3-C4-alkanediyl or C3-C 4 -alkenediyl or
- Q 1 particularly preferably represents hydrogen
- Q 2 particularly preferably represents hydrogen
- Q 4 , Q 5 and Q 6 are particularly preferably independently of one another hydrogen, methyl or ethyl
- Q 3 particularly preferably represents hydrogen, C1-C 4 - alkyl, C ⁇ -C4-alkoxy-C ⁇ -
- Q 3 and Q 4 particularly preferably together with the carbon atom to which they are attached, represent a saturated C5-C6- ing which is optionally simply substituted by methyl, methoxy or trifluoromethyl and in which a ring member is optionally replaced by oxygen or sulfur,
- G particularly preferably represents hydrogen (a) or one of the groups
- E represents a metal ion equivalent or an ammonium ion
- L represents oxygen or sulfur
- M represents oxygen or sulfur
- Rl particularly preferably represents C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 2 -alkyl which is optionally monosubstituted to trisubstituted by fluorine or chlorine or optionally C3 to C7 cycloalkyl which is monosubstituted or disubstituted by fluorine, chlorine, C 1 -C 5 -alkyl or C 1 -C 5 -alkoxy and in which one or two ring members which are not directly adjacent are replaced by oxygen and / or sulfur,
- phenyl-C4-C4-alkyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, C1-C4-alkyl, Cj-C4-alkoxy, C-C3-haloalkyl or C1-C3-haloalkoxy,
- R 2 particularly preferably represents in each case optionally mono- to trisubstituted by fluorine-substituted C 1 -C 12 -alkyl, C2-C 2 -alkenyl, C 1 -C 4 -alkoxy-C2-C3-alkyl or poly-C 1 -C 4 -alkoxy-C2 -C3 alkyl,
- C3-C7-cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, C1-C4-alkyl or C1-C4-alkoxy or
- R 3 particularly preferably represents Ci to Cg alkyl which is optionally three to five times substituted by fluorine or in each case optionally single to phenyl substituted twice by fluorine, chlorine, bromine, C1-C4-alkyl, C ⁇ -C alkoxy, C1-C3-haloalkyl, C ⁇ -C3-haloalkoxy, cyano or nitro,
- R and R5 are particularly preferably independently of one another Ci-Cg-alkyl, Cj-Cg-alkoxy, Ci-Cg-alkylamino, di- (-C -Cg-alkyl) amino, Ci -Cg-alkylthio, C3-C4- Alkenylthio, C3-Cg-Cycloalkylthio or for each optionally single to double by fluorine, chlorine, bromine, nitro, cyano, C ⁇ - C3- alkoxy, C ⁇ -C3-haloalkoxy, C ⁇ -C3-alkylthio, C ⁇ -C3-haloalkyl- thio, -C-C3-alkyl or C1-C3 -haloalkyl-substituted phenyl, phenoxy or phenylthio,
- R ° and R 7 independently of one another particularly preferably represent hydrogen, Ci-Cg-alkyl, C3-Cg-cycloalkyl, Ci-Cg-alkoxy, C3-Cg-alkenyl, Cj-Cg-alkoxy-Cj-Cg-alkyl, for phenyl optionally monosubstituted or disubstituted by fluorine, chlorine, bromine, C j -C 3 haloalkyl, C 1 -C 4 -alkyl or C1-C4 alkoxy, for monosubstituted or disubstituted by fluorine, chlorine, bromine, C1-C 4 - Alkyl, C1-C3-haloalkyl or C1-C4-alkoxy-substituted benzyl, or together with the nitrogen atom to which they are attached for a C4-C5-alkyl radical which is optionally substituted by methyl or ethyl, in which,
- halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
- X very particularly preferably represents chlorine, methyl, ethyl, n-propyl, iso-
- Z very particularly preferably represents a radical
- V 1 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso- Propoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano,
- V 2 very particularly preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy,
- W and Y very particularly preferably independently of one another represent hydrogen
- CKE very particularly preferably stands for one of the groups
- B very particularly preferably represents hydrogen, methyl or ethyl or A
- B and the carbon atom to which they are attached very particularly preferably represent saturated C 3 -C 7 -cycloalkyl, in which a ring member is optionally replaced by oxygen or sulfur and which, if appropriate, is substituted once or twice by methyl, ethyl, n Propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, trifluoromethyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy or tert .-Butoxy is substituted or
- A, B and the carbon atom to which they are attached very particularly preferably represent C5-C6-cycloalkyl or Cs-Cg-cycloalkenyl, in which two substituents together with the carbon atoms to which they are attached represent C2-C4-alkanediyl or C 2 -C 4 -alkenediyl, where in each case one methylene group is optionally replaced by oxygen or sulfur or are butadiene diyl,
- D very particularly preferably represents hydrogen, Cj-Cg-alkyl, C3-C4-alkenyl, C ⁇ -C3-alkoxy-C2-alkyl, C ⁇ -C3-alkylthio-C2-alkyl or C3-Cg-cycloalkyl, in which optionally a methylene group is replaced by oxygen or sulfur, or
- a and D together very particularly preferably represent C3-C4-alkanediyl, in which a carbon atom is optionally replaced by sulfur or
- a and D in the case of the compounds of the formula (II) together with the atoms to which they are attached very particularly preferably stand for one of the following groups AD:
- a and Q 1 together very particularly preferably represent C3-C4-alkanediyl or butenediyl or optionally substituted by methyl or methoxy
- Q 1 very particularly preferably represents hydrogen
- Q 2 very particularly preferably represents hydrogen
- Q 4 , Q 5 and Q 6 very particularly preferably independently of one another represent hydrogen, methyl or ethyl
- Q 3 very particularly preferably represents hydrogen, methyl, ethyl, propyl, n-butyl, phenyl or C3-Cg-cycloalkyl, in which a methylene group is optionally replaced by oxygen or sulfur or
- Q 3 and Q 4 very particularly preferably, together with the carbon to which they are attached, represent a saturated C 5 -C 6 ring which is optionally monosubstituted by methyl or methoxy and in which a ring member is optionally replaced by oxygen or sulfur,
- G very particularly preferably represents hydrogen (a) or one of the groups ° L 4 "'0 *' * '(C, / S0 ⁇ R3 (d) . ⁇ / ⁇ E),
- E represents a metal ion equivalent or an ammonium ion
- L represents oxygen or sulfur
- M oxygen or sulfur
- Rl very particularly preferably represents in each case optionally mono- to trisubstituted by fluorine or chlorine-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C - C 2 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 2 -alkylthio-C 1 -C 2 alkyl or optionally for C3-Cg-cycloalkyl which is simply substituted by fluorine, chlorine, methyl, ethyl, n-propyl, i-propyl or methoxy and in which one or two ring members which are not directly adjacent are optionally replaced by oxygen and / or sulfur,
- R 2 very particularly preferably represents C 1 -C 6 -alkyl, C2-Cg-alkenyl, C 1 -C 4 -alkoxy-C2-alkyl or poly-C 1 -C 4 -alkoxy-C2-alkyl,
- C3-Cg-cycloalkyl or for phenyl or benzyl which is optionally mono- to disubstituted by fluorine, chlorine, cyano, nitro, methyl, tert-butyl, methoxy, trifluoromethyl or trifluoromethoxy,
- R 3 very particularly preferably represents methyl, ethyl, n-propyl, isopropyl which is optionally trisubstituted by fluorine or in each case phenyl which is substituted by fluorine, chlorine, bromine, methyl, tert-butyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro .
- R and R ⁇ very particularly preferably independently of one another for C1-C4-alkyl, Cj-C4-alkoxy, C ⁇ ⁇ C4-alkylamino, di- (C ⁇ -C4-alkyl) amino, C1-C4-alkyl- or for each optionally phenyl, phenoxy or phenylthio substituted once or twice by fluorine, chlorine, bromine, nitro, cyano, methoxy, methyl, trifluoromethyl, trifluoromethoxy,
- R6 and R 7 independently of one another very particularly preferably represent hydrogen, for C 1 -C 4 -alkyl, C3-Cg-cycloalkyl, C 1 -C 4 -alkoxy, C3-C 4 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl , for phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, trifluoromethyl, methyl or methoxy, or together with the nitrogen atom to which they are attached for a C5-Cg-alkylene radical in which a methylene group is optionally replaced by oxygen or sulfur ,
- X particularly preferably represents chlorine, methyl or methoxy
- Z very particularly preferably represents a radical V 1 particularly preferably represents hydrogen, fluorine, chlorine, methyl, tert-butyl, methoxy, trifluoromethyl, trifluoromethoxy or nitro,
- V 2 particularly preferably represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl
- W and Y are particularly preferably, independently of one another, hydrogen or methyl
- CKE very particularly preferably stands for one of the groups
- B particularly preferably represents hydrogen or methyl
- A, B and the carbon atom to which they are attached are particularly preferably saturated C3-C7-cycloalkyl, in which a ring member is optionally replaced by oxygen and which is optionally mono- or disubstituted by methyl, ethyl, n-propyl, isopropyl, tert .
- -Butyl, methoxy, ethoxy, n-propoxy, n-butoxy or iso-butoxy is substituted or
- A, B and the carbon atom to which they are attached are particularly preferably C5-C6-cycloalkyl, where two substituents together with the carbon atoms to which they are attached are C 3 -C 4 -alkenediyl,
- D particularly preferably represents hydrogen
- Q 1 particularly preferably represents hydrogen
- Q 2 particularly preferably represents hydrogen
- Q 4 , Q 5 and Q 6 are particularly preferably independently of one another hydrogen, methyl or ethyl
- Q 3 particularly preferably represents hydrogen, methyl, ethyl, propyl, n-butyl,
- Q 3 and Q 4 particularly preferably together with the carbon to which they are attached represent a saturated Cs-Cg ring which is optionally monosubstituted by methyl or methoxy,
- G particularly preferably represents hydrogen (a) or one of the groups in which
- M represents oxygen or sulfur
- Rl particularly preferably represents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 2 -alkylthio-C 1 -C 2 -alkyl or, if appropriate, simply by fluorine, chlorine , Methyl or methoxy substituted C3-Cg-cycloalkyl,
- phenyl optionally substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy,
- R 2 particularly preferably represents Ci-Cg-alkyl, C2-Cg-alkenyl or C1-C4-alkoxy-C2-alkyl,
- W stands for hydrogen or methyl
- X stands for methyl, methoxy or chlorine
- Y stands for hydrogen or methyl
- A stands for methyl, i-propyl, s-butyl or cyclopropyl;
- A stands for hydrogen or methyl, if Het stands for group (5),
- A, B and the carbon atom to which they are attached are highlighted for saturated C3-C7-cycloalkyl, in which a ring member is optionally through
- Oxygen is replaced and which one or two if necessary by
- Q 3 stands for hydrogen, methyl, ethyl, n-butyl or phenyl
- Q 4 stands for hydrogen or methyl
- Q 3 and Q 4 are highlighted together with the carbon atom to which they are attached for a saturated Cs-Cg ring, Q 5 stands for hydrogen,
- G stands for hydrogen (a) or for one of the groups
- R 1 stands for C 1 -C 4 -alkyl or C 1 -C 2 alkoxy-C 1 -C 2 -alkyl
- R 2 stands for C 1 -C 4 -alkyl or phenyl.
- Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl can also be used in connection with heteroatoms, e.g. in alkoxy, where possible, be straight-chain or branched.
- optionally substituted radicals can be mono- or polysubstituted, and in the case of multiple substitutions the substituents can be the same or different.
- Cyclohexyl 1.18 (s, 3H, CH 3 cyclohexyl); 2.02 (s, 3H, Ar-CH3); 2.21 (s, 3H, Ar-CH3); 2.41 (d, IH, CH 2 CO); 2.47 (d, IH, CH 2 CO); 2.67 (s, 2H, CH 2 CO); 4.08 (q, 2H, CH 2 CH 3 ); 6.72 (s, IH, Ar-H); 7.17 (s, IH, Ar-H); 7.29 (d, 2H, Ar-H); 7.50 (d, 2H, Ar-H) ppm.
- Eluents for determination in the acidic range 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile.
- the calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive alkanones).
- the lambda max values were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
- the substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.
- Fungicides can be used to control Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and
- Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
- Some pathogens of fungal and bacterial are exemplary but not limiting
- Xanthomonas species such as, for example, Xanthomonas campestris pv. Oryzae
- Pseudomonas species such as, for example, Pseudomonas syringae pv. Lachrymans
- Erwinia species such as, for example, Erwinia amylovora;
- Pythium species such as, for example, Pythium ultimum
- Phytophthora species such as, for example, Phytophthora infestans
- Pseudoperonospora species such as, for example, Pseudoperonospora humuli or
- Plasmopara species such as, for example, Plasmopara viticola
- Bremia species such as, for example, Bremia lactucae
- Peronospora species such as, for example, Peronospora pisi or P. brassicae;
- Erysiphe species such as, for example, Erysiphe graminis
- Sphaerotheca species such as, for example, Sphaerotheca Sportsiginea;
- Podosphaera species such as, for example, Podosphaera leucotricha
- Venturia species such as, for example, Venturia inaequalis
- Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
- Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
- Cochliobolus species such as, for example, Cochliobolus sativus
- Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
- Uromyces species such as, for example, Uromyces appendiculatus
- Puccinia species such as, for example, Puccinia recondita
- Sclerotinia species such as, for example, Sclerotinia sclerotiorum
- Tilletia species such as, for example, Tilletia caries
- Ustilago species such as, for example, Ustilago nuda or Ustilago avenae;
- Pellicularia species such as, for example, Pellicularia sasakii;
- Pyricularia species such as, for example, Pyricularia oryzae
- Fusarium species such as, for example, Fusarium culmorum
- Botrytis species such as, for example, Botrytis cinerea
- Septoria species such as, for example, Septoria nodorum
- Leptosphaeria species such as, for example, Leptosphaeria nodorum
- Cercospora species such as, for example, Cercospora canescens
- Alternaria species such as, for example, Alternaria brassicae;
- Pseudocercosporella species such as, for example, Pseudocercosporella herpotrichoides.
- the active compounds according to the invention also have a very good strengthening effect in plants. They are therefore suitable for mobilizing the plant's own defenses against attack by unwanted microorganisms.
- plant-strengthening (resistance-inducing) substances are to be understood as those substances which are able to stimulate the defense system of plants in such a way that the treated plants largely undergo subsequent inocolation with undesirable microorganisms
- Undesired microorganisms are to be understood in the present case as phytopathogenic fungi, bacteria and viruses.
- the substances according to the invention can therefore be used to remove plants within a certain period of time
- the period within which protection is brought about generally extends from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active compounds.
- the active compounds according to the invention can be used with particularly good success to combat diseases in wine, fruit and vegetable cultivation, such as, for example, against Venturia or Podosphaera species.
- the active compounds according to the invention are also suitable for increasing the crop yield.
- the active compounds according to the invention can also be used as herbicides, for influencing plant growth, and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of further active compounds.
- Plants and parts of plants can be treated with the active compounds according to the invention.
- Plants are understood here to mean all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants).
- Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic ones
- Plants and including plant varieties that can or cannot be protected by plant breeders' rights Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as sprout, leaf, flower and root, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
- the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
- the treatment of the plants and parts of plants with the active compounds according to the invention takes place directly or by acting on their environment, habitat or Storage space according to the usual treatment methods, for example by dipping, spraying, evaporating, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by means of single-layer or multi-layer coating.
- the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
- technical materials are to be understood as non-living materials that have been prepared for use in technology.
- technical materials which are to be protected from microbial change or destruction by active substances according to the invention can be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which are attacked or decomposed by microorganisms can be.
- adhesives glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which are attacked or decomposed by microorganisms can be.
- Materials are also parts of production systems, such as cooling water circuits, that can be affected by the proliferation of microorganisms.
- technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer liquids, particularly preferably wood.
- Bacteria, fungi, yeasts, algae and slime organisms may be mentioned as microorganisms which can cause degradation or a change in the technical materials.
- the active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
- microorganisms of the following genera may be mentioned:
- Alternaria such as Alternaria tenuis, Aspergillus, such as Aspergillus niger,
- Chaetomium like Chaetomium globosum
- Coniophora such as Coniophora puetana
- Lentinus such as Lentinus tigrinus
- Penicillium such as Penicillium glaucum
- Polyporus such as Polyporus versicolor
- Aureobasidium such as Aureobasidium pullulans
- Sclerophoma such as Sclerophoma pityophila
- Trichoderma like Trichoderma viride
- Escherichia such as Escherichia coli
- Pseudomonas such as Pseudomonas aeruginosa
- Staphylococcus such as Staphylococcus aureus.
- the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV -Cold and warm mist formulations.
- These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and or dispersants and / or foam-generating agents.
- organic solvents can, for example, also be used as auxiliary solvents.
- auxiliary solvents include aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions,
- Alcohols such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water.
- Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and pressure, e.g. aerosol
- Propellants such as halogenated hydrocarbons, butane, propane, nitrogen and carbon dioxide.
- Possible solid carriers are: e.g. natural rock meals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock meals, such as highly disperse silica, aluminum oxide and silicates.
- the following are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems.
- Possible emulsifiers and / or foaming agents are: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
- Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
- Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phosphohpides, such as cephalins and lecithins, and synthetic phosphohpides.
- Other additives can be mineral and vegetable oils.
- Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
- the formulations generally contain between 0.1 and 95 percent by weight
- Active ingredient preferably between 0.5 and 90%.
- the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the spectrum of activity or to prevent the development of resistance.
- fungicides bactericides
- acaricides nematicides or insecticides
- synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
- Famoxadon Fenapanil, Fenarimol, Fenbuconazol, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimo ⁇ h, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flu ⁇ rimidol, Flusrimidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,
- Imazalil Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione, Iprovalicarb,
- Kasugamycin, Kresoxim-methyl, copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture, Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
- Oxadixyl Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
- Paclobutrazole pefurazoate, penconazole, pencycuron, phosdiphen, picoxystrobin, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidone,
- Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetcyclacis, tetraconazole, thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram, dioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutichl, triazoxid, triazoxid, triazoxide, triazoxide
- Tridemo ⁇ h Trifloxystrobin, triflumizole, triforin, triticonazole,
- N-formyl-N-hydroxy-DL-alanine sodium salt O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate,
- Cadusafos Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron,
- Chlormephos Chlo ⁇ yrifos, Chlo ⁇ yrifos M, Chlovaporthrin, Chromafenozide, Cis- Resmethrin, Cispermethrin, Clocythrin, Cloethocarb, Clofentezine, Clothianidine, Cyanophos, Cycloprene, Cycloprothrin, Cyfluthrin, Cyhalothrinomethine, Cyatin
- Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
- Paecilomyces fumosoroseus Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propargite, Propoxur, Prothiofos, Prothrohrinos, Pothrohrinos, Pothrohrine, Pothrohrinate , Pyridaben, pyridathione,
- the compounds of formula (I) according to the invention also have very good antifungal effects. They have a very broad spectrum of antimycotic effects, especially against dermatophytes and shoots, mold and diphasic fungi (e.g. against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as
- the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to use the active compounds
- the application rates can be varied within a relatively wide range, depending on the type of application.
- the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
- the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and
- the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
- plants and their parts can be treated with active substances according to the invention.
- plant species and plant cultivars and their parts occurring wildly or obtained by conventional organic breeding methods, such as crossing or protoplast fusion are treated.
- transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetic modified organisms) and their parts are treated.
- the term "parts” or “parts of plants” or “plant parts” was explained above.
- Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
- plant varieties are plants with new properties ("traits"), which have been grown by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, breeds, bio and genotypes.
- the treatment according to the invention can also cause superadditive ("synergistic") effects. For example, reduced application rates and / or widening of the activity spectrum and / or an increase in the action of the substances and agents which can be used according to the invention, better plant growth, are increased
- transgenic plants or plant cultivars to be treated according to the invention include all plants which, through the genetic engineering modification, have received genetic material which contains them
- traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher crop yields, higher quality and / or higher
- Nutritional value of the crop products higher shelf life and / or workability of the crop products. Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients.
- the important ones are examples of transgenic plants Cultivated plants such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pumice, citrus fruits and grapes) are mentioned, with corn, soybeans, potatoes, cotton and rapeseed being particularly emphasized.
- the properties (“traits”) are particularly emphasized of the plants' increased defense against insects by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), CryIA (b ), Cry ⁇ A (c), CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
- the properties (“traits”) also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
- the properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas,
- Glyphosate or phosphinotricin e.g. "PAT” gene.
- the genes imparting the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
- “Bt plants” are corn varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YIELD GARD® (e.g. corn, cotton, soybeans), KnockOut®
- herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties that are sold under the trade names Roundup Ready® (tolerance against glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance against
- Phosphinotricin such as rapeseed
- IMI® tolerance against imidazolinones
- STS® tolerance against sulfonylureas such as maize
- the herbicide-resistant plants include the varieties sold under the name Clearfield® (eg maize). Of course, these statements also apply to future developed or future plant varieties with these or future-developed genetic traits.
- the plants listed can be treated particularly advantageously with the compounds of the general formula (I) according to the invention.
- the preferred ranges given above for the active ingredients also apply to the treatment of these plants.
- Plant treatment with the compounds specifically listed in the present text should be particularly emphasized.
- dimethylacetamide emulsifier 1.0 part by weight of alkyl aryl polyglycol ether
- active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
- Apple scab pathogen Venturia inaequalis and then remain in an incubation cabin for 1 day at approx. 20 ° C and 100% relative humidity.
- the plants are then placed in the greenhouse at approx. 21 ° C. and a relative humidity of approx. 90%.
- Botrytis test (bean) / protective
- dimethylacetamide emulsifier 1.0 part by weight of alkyl aryl polyglycol ether
- active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
- the inoculated plants are placed in a darkened chamber at approx. 20 ° C and 100% relative humidity.
- Botrytis test (bean) / protective
- the medium was previously treated with a suitable concentration of spores or
- Mycelium of the fungus to be tested is offset.
- the resulting concentrations of the active ingredient are 0.1, 1, 10 and 100 ppm.
- the resulting concentration of the emulsifier is 300 ppm.
- the plates are then incubated for 3-5 days on a shaker at a temperature of 22 ° C. until sufficient growth can be determined in the untreated control.
- the evaluation is carried out photometrically at a wavelength of 620 nm
- Measured data of the various concentrations are used to calculate the dose of active ingredient which leads to a 50% inhibition of fungal growth compared to the untreated control (ED 50 ).
- Emulsifier 1 part by weight of alkylaryl polyglycol ether
- active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
- Temperature of about 20 ° C and a relative humidity of about 80% set up to promote the development of mildew pustules.
- Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
- Solvent 50 parts by weight of N, N-dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
- active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the concentrate is diluted to the desired concentration with water and the stated amount of emulsifier.
- Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
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- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2003206693A AU2003206693A1 (en) | 2002-01-15 | 2003-01-03 | Fungicidal biphenyl substituted cyclic ketoenols |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2002101239 DE10201239A1 (de) | 2002-01-15 | 2002-01-15 | Fungizide biphenylsubstituierte cyclische Ketoenole |
DE10201239.3 | 2002-01-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2003059065A1 true WO2003059065A1 (fr) | 2003-07-24 |
Family
ID=7712156
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2003/000026 WO2003059065A1 (fr) | 2002-01-15 | 2003-01-03 | Ceto-enols cycliques substitues par un biphenyle |
Country Status (3)
Country | Link |
---|---|
AU (1) | AU2003206693A1 (fr) |
DE (1) | DE10201239A1 (fr) |
WO (1) | WO2003059065A1 (fr) |
Cited By (23)
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WO2008067910A1 (fr) * | 2006-12-04 | 2008-06-12 | Bayer Cropscience Ag | Dérivés d'acide tétramique cis-alcoxyspirocycliques substitués par le biphényle |
WO2008067911A1 (fr) * | 2006-12-04 | 2008-06-12 | Bayer Cropscience Ag | Cétoénols spirocycliques substitués par le biphényle |
EP2071952A1 (fr) | 2007-12-21 | 2009-06-24 | Bayer CropScience AG | Utilisation de dérivés d'acide tétramique pour lutter contre les phytopathogènes par une application par irrigation ou au goutte-à-goutte |
JP2009538844A (ja) * | 2006-06-02 | 2009-11-12 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | アルコキシアルキル置換環状ケトエノール |
EP2127522A1 (fr) * | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Combinaisons de principes actifs presentant des propriétés insecticides et acaricides |
WO2010081686A1 (fr) * | 2009-01-19 | 2010-07-22 | Bayer Cropscience Ag | 1,3-diones bicycliques et leur utilisation comme insecticides, acaricides et/ou fongicides |
WO2010127797A3 (fr) * | 2009-05-06 | 2011-04-14 | Bayer Cropscience Ag | Composés de cyclopentanedione et leur utilisation comme insecticides, acaricides et/ou fongicides |
WO2010081688A3 (fr) * | 2009-01-19 | 2011-05-05 | Bayer Cropscience Ag | 4-phényl-pyrane-3,5-diones, 4-phényl-thiopyrane-3,5-diones et cyclohexanetriones et leur utilisation comme insecticides, acaricides et/ou fongicides |
WO2011098440A2 (fr) | 2010-02-10 | 2011-08-18 | Bayer Cropscience Ag | Cétoénols cyliques à substitution biphényle |
JP2012515190A (ja) * | 2009-01-19 | 2012-07-05 | シンジェンタ リミテッド | シクロペンタジオン由来の除草剤 |
WO2012101047A1 (fr) | 2011-01-25 | 2012-08-02 | Bayer Cropscience Ag | Procédé de production de dérivés de la 1-h-pyrrolidine-2,4-dione |
WO2012110518A1 (fr) | 2011-02-17 | 2012-08-23 | Bayer Pharma Aktiengesellschaft | 3-(biphenyl-3-yl)-8,8-difluoro-4-hydroxy-l-azaspiro[4.5]déc-3-en-2-one substitués utilisés à des fins thérapeutiques |
WO2012116960A1 (fr) | 2011-03-01 | 2012-09-07 | Bayer Cropscience Ag | 2-acyloxy-pyrrolin-4-ones |
WO2012165648A1 (fr) | 2011-05-30 | 2012-12-06 | Sumitomo Chemical Company, Limited | Composés cyclohexanones et herbicides les comprenant |
WO2013020888A1 (fr) | 2011-08-05 | 2013-02-14 | Bayer Intellectual Property Gmbh | Utilisation de dérivés d'acide tétramique pour la lutte contre les pathogènes par application foliaire |
US8389443B2 (en) | 2008-12-02 | 2013-03-05 | Bayer Cropscience Ag | Geminal alkoxy/alkylspirocyclic substituted tetramate derivatives |
US8435549B2 (en) | 2007-09-25 | 2013-05-07 | Bayer Cropscience Ag | Halogen alkoxy spirocyclic tetramic and tetronic acid derivatives |
US8518985B2 (en) | 2009-03-11 | 2013-08-27 | Bayer Cropscience Ag | Haloalkylmethyleneoxyphenyl-substituted ketoenols |
JP2014504624A (ja) * | 2011-02-06 | 2014-02-24 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 処置用の(5s,8s)−3−(4’−クロロ−3’−フルオロ−4−メチルビフェニル−3−イル)−4−ヒドロキシ−8−メトキシ−1−アザスピロ[4.5]デカ−3−エン−2−オン(化合物A) |
JP2014040436A (ja) * | 2003-08-14 | 2014-03-06 | Bayer Cropscience Ag | 4−ビフェニル置換ピラゾリジン−3,5−ジオン誘導体 |
WO2014084410A1 (fr) | 2012-11-30 | 2014-06-05 | Sumitomo Chemical Company, Limited | Composés cyclohexanones et herbicides les comprenant |
US8846946B2 (en) | 2008-12-02 | 2014-09-30 | Bayer Cropscience Ag | Germinal alkoxy/alkylspirocyclic substituted tetramate derivatives |
US8859466B2 (en) | 2007-08-02 | 2014-10-14 | Bayer Cropscience Ag | Oxaspirocyclic spiro-substituted tetramic acid and tetronic acid derivatives |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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WO1999048869A1 (fr) * | 1998-03-26 | 1999-09-30 | Bayer Aktiengesellschaft | Cetoenols cycliques a substitution arylphenyle |
JP2001026578A (ja) * | 1999-05-11 | 2001-01-30 | Sankyo Co Ltd | N−置換ジヒドロピロール誘導体 |
WO2001009092A1 (fr) * | 1999-07-30 | 2001-02-08 | Bayer Aktiengesellschaft | Ceto-enols cycliques a substitution biphenyle comme produits antiparasites |
-
2002
- 2002-01-15 DE DE2002101239 patent/DE10201239A1/de not_active Withdrawn
-
2003
- 2003-01-03 WO PCT/EP2003/000026 patent/WO2003059065A1/fr not_active Application Discontinuation
- 2003-01-03 AU AU2003206693A patent/AU2003206693A1/en not_active Abandoned
Patent Citations (3)
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WO1999048869A1 (fr) * | 1998-03-26 | 1999-09-30 | Bayer Aktiengesellschaft | Cetoenols cycliques a substitution arylphenyle |
JP2001026578A (ja) * | 1999-05-11 | 2001-01-30 | Sankyo Co Ltd | N−置換ジヒドロピロール誘導体 |
WO2001009092A1 (fr) * | 1999-07-30 | 2001-02-08 | Bayer Aktiengesellschaft | Ceto-enols cycliques a substitution biphenyle comme produits antiparasites |
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PATENT ABSTRACTS OF JAPAN vol. 2000, no. 16 8 May 2001 (2001-05-08) * |
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JP2009538844A (ja) * | 2006-06-02 | 2009-11-12 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | アルコキシアルキル置換環状ケトエノール |
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AU2007327961B2 (en) * | 2006-12-04 | 2013-08-22 | Bayer Intellectual Property Gmbh | Biphenyl-substituted spirocyclic ketoenols |
WO2008067910A1 (fr) * | 2006-12-04 | 2008-06-12 | Bayer Cropscience Ag | Dérivés d'acide tétramique cis-alcoxyspirocycliques substitués par le biphényle |
JP2010511642A (ja) * | 2006-12-04 | 2010-04-15 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | シス−アルコキシスピロ環式ビフェニル置換されたテトラミン酸誘導体 |
JP2010511643A (ja) * | 2006-12-04 | 2010-04-15 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | ビフェニル置換されたスピロ環式ケトエノール |
US8993782B2 (en) * | 2006-12-04 | 2015-03-31 | Bayer Cropscience Ag | Cis-alkoxyspirocyclic biphenyl-substituted tetramic acid derivatives |
KR101571752B1 (ko) | 2006-12-04 | 2015-11-25 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 비페닐-치환된 스피로사이클릭 케토에놀 |
US9000189B2 (en) | 2006-12-04 | 2015-04-07 | Bayer Cropscience Ag | Biphenyl-substituted spirocyclic ketoenols |
US20110130284A1 (en) * | 2006-12-04 | 2011-06-02 | Bayer Cropscience Ag | Cis-alkoxyspirocyclic biphenyl-substituted tetramic acid derivatives |
US8859466B2 (en) | 2007-08-02 | 2014-10-14 | Bayer Cropscience Ag | Oxaspirocyclic spiro-substituted tetramic acid and tetronic acid derivatives |
US8435549B2 (en) | 2007-09-25 | 2013-05-07 | Bayer Cropscience Ag | Halogen alkoxy spirocyclic tetramic and tetronic acid derivatives |
EP2071952A1 (fr) | 2007-12-21 | 2009-06-24 | Bayer CropScience AG | Utilisation de dérivés d'acide tétramique pour lutter contre les phytopathogènes par une application par irrigation ou au goutte-à-goutte |
WO2009146793A3 (fr) * | 2008-05-29 | 2010-05-14 | Bayer Cropscience Ag | Combinaisons de principes actifs à propriétés insecticides et acaricides |
EP2127522A1 (fr) * | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Combinaisons de principes actifs presentant des propriétés insecticides et acaricides |
US8389443B2 (en) | 2008-12-02 | 2013-03-05 | Bayer Cropscience Ag | Geminal alkoxy/alkylspirocyclic substituted tetramate derivatives |
US8846946B2 (en) | 2008-12-02 | 2014-09-30 | Bayer Cropscience Ag | Germinal alkoxy/alkylspirocyclic substituted tetramate derivatives |
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US9204640B2 (en) | 2011-03-01 | 2015-12-08 | Bayer Intellectual Property Gmbh | 2-acyloxy-pyrrolin-4-ones |
US9101140B2 (en) | 2011-05-30 | 2015-08-11 | Sumitomo Chemical Company, Limited | Cyclohexanone compounds and herbicides comprising the same |
WO2012165648A1 (fr) | 2011-05-30 | 2012-12-06 | Sumitomo Chemical Company, Limited | Composés cyclohexanones et herbicides les comprenant |
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WO2014084410A1 (fr) | 2012-11-30 | 2014-06-05 | Sumitomo Chemical Company, Limited | Composés cyclohexanones et herbicides les comprenant |
Also Published As
Publication number | Publication date |
---|---|
DE10201239A1 (de) | 2003-07-24 |
AU2003206693A1 (en) | 2003-07-30 |
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