SK79996A3 - Aryl acetic acid derivatives, preparation method thereof and their use as fungicides - Google Patents

Aryl acetic acid derivatives, preparation method thereof and their use as fungicides Download PDF

Info

Publication number: SK79996A3
Authority: SK; Slovakia
Prior art keywords: group; optionally; carbon atoms; substituted; butyl
Prior art date: 1993-12-22

Application number

SK799-96A

Other languages

English (en)

Slovak (sk)

Inventor

Gerd Kleefeld

Ralf Tiemann

Peter Gerdes

Ulrich Heinemann

Heinz-Wilhelm Dehne

Stefan Dutzmann

Klaus Stenzel

Original Assignee

Bayer Ag

Priority date (The priority date 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 date listed.)

1993-12-22

Filing date

1994-12-09

Publication date

1997-03-05

1994-12-09 Application filed by Bayer Ag filed Critical Bayer Ag

1997-03-05 Publication of SK79996A3 publication Critical patent/SK79996A3/sk

Links

-1 Aryl acetic acid derivatives Chemical class 0.000 title claims abstract description 186
239000000417 fungicide Substances 0.000 title claims abstract description 8
238000002360 preparation method Methods 0.000 title claims description 26
238000000034 method Methods 0.000 claims abstract description 27
238000004519 manufacturing process Methods 0.000 claims abstract description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 62
150000001875 compounds Chemical class 0.000 claims description 46
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
239000011737 fluorine Substances 0.000 claims description 33
229910052731 fluorine Inorganic materials 0.000 claims description 33
239000000460 chlorine Substances 0.000 claims description 32
229910052801 chlorine Inorganic materials 0.000 claims description 30
229910052736 halogen Inorganic materials 0.000 claims description 30
125000004430 oxygen atom Chemical group O* 0.000 claims description 30
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 29
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 27
125000001449 isopropyl group Chemical class [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 27
125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 claims description 27
150000002367 halogens Chemical group 0.000 claims description 26
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 25
125000001113 thiadiazolyl group Chemical group 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 24
229910052717 sulfur Inorganic materials 0.000 claims description 22
125000001188 haloalkyl group Chemical group 0.000 claims description 20
125000005843 halogen group Chemical group 0.000 claims description 20
125000004434 sulfur atom Chemical group 0.000 claims description 20
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 18
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
125000004093 cyano group Chemical group *C#N 0.000 claims description 17
229910052794 bromium Inorganic materials 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 16
229910052757 nitrogen Inorganic materials 0.000 claims description 16
125000001153 fluoro group Chemical group F* 0.000 claims description 15
125000002098 pyridazinyl group Chemical group 0.000 claims description 15
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([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
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
125000000335 thiazolyl group Chemical group 0.000 claims description 13
125000004414 alkyl thio group Chemical group 0.000 claims description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
125000003282 alkyl amino group Chemical group 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
125000004663 dialkyl amino group Chemical group 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 11
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
125000003373 pyrazinyl group Chemical group 0.000 claims description 8
125000000547 substituted alkyl group Chemical group 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
239000003153 chemical reaction reagent Substances 0.000 claims description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 6
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
125000002541 furyl group Chemical group 0.000 claims description 6
125000001072 heteroaryl group Chemical group 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 5
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
125000004438 haloalkoxy group Chemical group 0.000 claims description 5
125000001786 isothiazolyl group Chemical group 0.000 claims description 5
125000000842 isoxazolyl group Chemical group 0.000 claims description 5
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
125000003302 alkenyloxy group Chemical group 0.000 claims description 4
125000004666 alkoxyiminoalkyl group Chemical group 0.000 claims description 4
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 4
125000000262 haloalkenyl group Chemical group 0.000 claims description 4
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 4
125000005549 heteroarylene group Chemical group 0.000 claims description 4
125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
125000002971 oxazolyl group Chemical group 0.000 claims description 4
125000004306 triazinyl group Chemical group 0.000 claims description 4
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 4
150000001350 alkyl halides Chemical class 0.000 claims description 3
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 3
125000004995 haloalkylthio group Chemical group 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 3
125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 2
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000000033 alkoxyamino group Chemical group 0.000 claims description 2
125000005277 alkyl imino group Chemical group 0.000 claims description 2
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
125000005133 alkynyloxy group Chemical group 0.000 claims description 2
125000000732 arylene group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
230000000855 fungicidal effect Effects 0.000 claims description 2
125000005291 haloalkenyloxy group Chemical group 0.000 claims description 2
125000005700 haloalkyleneoxy group Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
239000012433 hydrogen halide Substances 0.000 claims description 2
229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
125000004957 naphthylene group Chemical group 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Chemical group 0.000 claims description 2
125000000109 phenylethoxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])O* 0.000 claims description 2
125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
125000005650 substituted phenylene group Chemical group 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
208000031888 Mycoses Diseases 0.000 claims 2
125000003226 pyrazolyl group Chemical group 0.000 claims 2
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
241000233866 Fungi Species 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 claims 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
239000000945 filler Substances 0.000 claims 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
125000003258 trimethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
241000196324 Embryophyta Species 0.000 description 22
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
239000003995 emulsifying agent Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 13
239000007858 starting material Substances 0.000 description 11
239000004480 active ingredient Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
125000005605 benzo group Chemical group 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
230000001681 protective effect Effects 0.000 description 8
238000005507 spraying Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000002877 alkyl aryl group Chemical group 0.000 description 6
238000011081 inoculation Methods 0.000 description 6
229920000151 polyglycol Polymers 0.000 description 6
239000010695 polyglycol Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000000725 suspension Substances 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
240000005979 Hordeum vulgare Species 0.000 description 5
235000007340 Hordeum vulgare Nutrition 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
238000011156 evaluation Methods 0.000 description 5
239000008187 granular material Substances 0.000 description 5
VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
241000228453 Pyrenophora Species 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
239000013543 active substance Substances 0.000 description 4
239000000969 carrier Substances 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000000126 substance Substances 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
241000221787 Erysiphe Species 0.000 description 3
239000004606 Fillers/Extenders Substances 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000896242 Podosphaera Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
241000579741 Sphaerotheca <fungi> Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
241000317942 Venturia <ichneumonid wasp> Species 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
239000000975 dye Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
239000007788 liquid Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
235000011181 potassium carbonates Nutrition 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000011435 rock Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000002689 soil Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
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WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 2
241000895523 Blumeria graminis f. sp. hordei Species 0.000 description 2
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241000228437 Cochliobolus Species 0.000 description 2
241000371644 Curvularia ravenelii Species 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
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CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
241000228452 Venturia inaequalis Species 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
235000021016 apples Nutrition 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
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238000004440 column chromatography Methods 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000012973 diazabicyclooctane Substances 0.000 description 2
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239000004408 titanium dioxide Substances 0.000 description 1
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Classifications

- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
- 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
- A01N37/44—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 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/50—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 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/52—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
- 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/32—Oxygen atoms
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Environmental Sciences (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Agronomy & Crop Science (AREA)
Zoology (AREA)
Pest Control & Pesticides (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Pyridine Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SK799-96A 1993-12-22 1994-12-09 Aryl acetic acid derivatives, preparation method thereof and their use as fungicides SK79996A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE4343829		1993-12-22
DE4424788A DE4424788A1 (de)	1993-12-22	1994-07-14	Arylessigsäurederivate
PCT/EP1994/004103 WO1995017376A1 (de)	1993-12-22	1994-12-09	Arylessigsäurederivate und ihre verwendung als fungizide

Publications (1)

Publication Number	Publication Date
SK79996A3 true SK79996A3 (en)	1997-03-05

Family

ID=25932345

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK799-96A SK79996A3 (en)	1993-12-22	1994-12-09	Aryl acetic acid derivatives, preparation method thereof and their use as fungicides

Country Status (19)

Country	Link
EP (1)	EP0736001B1 (cs)
JP (1)	JPH09507218A (cs)
CN (1)	CN1055461C (cs)
AT (1)	ATE181056T1 (cs)
AU (1)	AU1313295A (cs)
BG (1)	BG100661A (cs)
BR (1)	BR9408392A (cs)
CZ (1)	CZ176196A3 (cs)
DE (2)	DE4424788A1 (cs)
ES (1)	ES2132609T3 (cs)
HU (1)	HUT74123A (cs)
IL (1)	IL112020A0 (cs)
MY (1)	MY131693A (cs)
PL (1)	PL315141A1 (cs)
SK (1)	SK79996A3 (cs)
TR (1)	TR28332A (cs)
TW (1)	TW316222B (cs)
WO (1)	WO1995017376A1 (cs)
ZA (1)	ZA9410181B (cs)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5583249A (en) *	1994-08-19	1996-12-10	Ciba-Geigy Corporation	Pesticides
US5710314A (en) *	1994-09-30	1998-01-20	Novartis Corporation	Microbicides
DE19525969A1 (de) *	1995-07-17	1997-01-23	Bayer Ag	Etherderivate
HUP9900736A2 (hu) *	1995-10-18	1999-06-28	Bayer Ag.	Fluor-metoxi-akrilsav-származékok és kártevőirtó szerként történő alkalmazásuk
DE19611653A1 (de) *	1995-10-18	1997-04-24	Bayer Ag	Fluormethoxyacrylsäurederivate
IN183755B (cs) *	1996-05-28	2000-04-01	Sumitomo Chemical Co
DE19642530A1 (de) *	1996-10-15	1998-04-16	Bayer Ag	Halogenalkoximinoessigsäureamide
DE19723195A1 (de) *	1997-06-03	1998-12-10	Bayer Ag	Fluormethoximinoverbindungen
UA73307C2 (uk)	1999-08-05	2005-07-15	Куміаі Кемікал Індастрі Ко., Лтд.	Похідна карбамату і фунгіцид сільськогосподарського/садівницького призначення
EP1244633A1 (de)	1999-12-22	2002-10-02	Bayer Aktiengesellschaft	Pyrazolylbenzyletherderivate die eine fluormethoxyimino gruppe besitzen und ihre verwendung als schädlingsbekämpfungsmittel
WO2002062759A1 (en) *	2001-02-02	2002-08-15	Kumiai Chemical Industry Co., Ltd.	Iminooxymethylpyridine compound and agricultural or horticultural bactericide
WO2005081954A2 (en)	2004-02-25	2005-09-09	Wyeth	Inhibitors of protein tyrosine phosphatase 1b
AR081626A1 (es)	2010-04-23	2012-10-10	Cytokinetics Inc	Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos
AR081331A1 (es)	2010-04-23	2012-08-08	Cytokinetics Inc	Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos
US9133123B2 (en)	2010-04-23	2015-09-15	Cytokinetics, Inc.	Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use
US8759380B2 (en)	2011-04-22	2014-06-24	Cytokinetics, Inc.	Certain heterocycles, compositions thereof, and methods for their use
CN106431977B (zh) *	2015-08-12	2018-11-02	沈阳中化农药化工研发有限公司	一种不饱和肟醚类化合物及其用途
CN115215761A (zh) *	2021-04-15	2022-10-21	湖南大学	二苯肟醚衍生物及其作为杀菌剂和杀虫剂的用途

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Publication number	Priority date	Publication date	Assignee	Title
DE3917352A1 (de) *	1989-05-27	1990-11-29	Basf Ag	Neue oximether und diese enthaltende fungizide

1994
- 1994-07-14 DE DE4424788A patent/DE4424788A1/de not_active Withdrawn
- 1994-11-21 TW TW083110791A patent/TW316222B/zh active
- 1994-12-09 CN CN94194636A patent/CN1055461C/zh not_active Expired - Fee Related
- 1994-12-09 HU HU9601694A patent/HUT74123A/hu unknown
- 1994-12-09 DE DE59408399T patent/DE59408399D1/de not_active Expired - Fee Related
- 1994-12-09 BR BR9408392A patent/BR9408392A/pt not_active Application Discontinuation
- 1994-12-09 WO PCT/EP1994/004103 patent/WO1995017376A1/de not_active Ceased
- 1994-12-09 AT AT95904446T patent/ATE181056T1/de not_active IP Right Cessation
- 1994-12-09 CZ CZ961761A patent/CZ176196A3/cs unknown
- 1994-12-09 PL PL94315141A patent/PL315141A1/xx unknown
- 1994-12-09 SK SK799-96A patent/SK79996A3/sk unknown
- 1994-12-09 EP EP95904446A patent/EP0736001B1/de not_active Expired - Lifetime
- 1994-12-09 ES ES95904446T patent/ES2132609T3/es not_active Expired - Lifetime
- 1994-12-09 JP JP7517137A patent/JPH09507218A/ja not_active Ceased
- 1994-12-09 AU AU13132/95A patent/AU1313295A/en not_active Abandoned
- 1994-12-13 MY MYPI94003329A patent/MY131693A/en unknown
- 1994-12-15 TR TR01303/94A patent/TR28332A/xx unknown
- 1994-12-19 IL IL11202094A patent/IL112020A0/xx unknown
- 1994-12-21 ZA ZA9410181A patent/ZA9410181B/xx unknown
1996
- 1996-06-17 BG BG100661A patent/BG100661A/xx unknown

Also Published As

Publication number	Publication date
DE59408399D1 (de)	1999-07-15
PL315141A1 (en)	1996-10-14
BR9408392A (pt)	1997-08-19
TW316222B (cs)	1997-09-21
MY131693A (en)	2007-08-30
EP0736001A1 (de)	1996-10-09
TR28332A (tr)	1996-05-06
CN1139426A (zh)	1997-01-01
WO1995017376A1 (de)	1995-06-29
AU1313295A (en)	1995-07-10
IL112020A0 (en)	1995-03-15
ZA9410181B (en)	1995-08-25
DE4424788A1 (de)	1995-06-29
ATE181056T1 (de)	1999-06-15
EP0736001B1 (de)	1999-06-09
HUT74123A (en)	1996-11-28
CZ176196A3 (en)	1997-03-12
JPH09507218A (ja)	1997-07-22
CN1055461C (zh)	2000-08-16
ES2132609T3 (es)	1999-08-16
BG100661A (en)	1997-02-28

Publication	Publication Date	Title
SK79996A3 (en)	1997-03-05	Aryl acetic acid derivatives, preparation method thereof and their use as fungicides
EA011928B1 (ru)	2009-06-30	Замещённые гетероароилом фенилаланин-амиды
EP0628540B1 (de)	1999-01-20	2-Oximino-2-phenyl-acetamide
JPH05112541A (ja)	1993-05-07	トリアジニル置換アクリル酸エステル
EP0584625B1 (de)	1997-03-26	Pyridyloxy-acrylsäureester
EP0384211B1 (de)	1994-09-07	Substituierte Acrylsäureester
JPH11500103A (ja)	1999-01-06	置換されたカルボン酸アミド及びその殺菌・殺カビ剤としての使用
SK282154B6 (sk)	2001-11-06	Derivát iminooxymetylénanilidu, spôsob jeho prípravy, medziprodukty na jeho prípravu a prostriedok na ničenie škodcov s jeho obsahom
AU686304B2 (en)	1998-02-05	Phenylthio acetic acid derivatives, process and intermediateproducts for their production and agents containing them
US5420160A (en)	1995-05-30	1-alkoxyhexatriene-2-carboxylates
KR100297332B1 (ko)	2001-10-24	해충구제제로서의피리딜-1,2,4-티아디아졸
US5369124A (en)	1994-11-29	Substituted thiophenecarboxamides
JPH0578335A (ja)	1993-03-30	三置換１，２，４−トリアジン−３，５−ジオン及び新規中間体
JP3535556B2 (ja)	2004-06-07	シクロアルキルカルボキシアニリド
US4849435A (en)	1989-07-18	Fungicidal 1-aminomethyl-3-aryl-4-cyano-pyrroles
JPH10505075A (ja)	1998-05-19	イミジン酸誘導体及びその有害生物防除剤としての使用
JPH01249753A (ja)	1989-10-05	複素環で置換されたアクリル酸エステル
JP3162530B2 (ja)	2001-05-08	置換されたピリジルピリミジン
KR19990023015A (ko)	1999-03-25	카복실산 아미드 유도체 및 농약으로서의 그의 용도
RU2167853C2 (ru)	2001-05-27	Амиды алкоксиминоуксусной кислоты, фунгицидное средство на их основе и способ борьбы с грибковыми заболеваниями растений
CA2057293A1 (en)	1992-06-13	Substituted pyrimidylamide oximes
HU202367B (en)	1991-03-28	Fungicide and bactericide compositions containing pyrimidine derivative as active components and process for producing new pyrimidine derivatives
DE4328385A1 (de)	1995-03-02	2-Oximino-2-pyridyl-essigsäurederivate
US4742070A (en)	1988-05-03	Arylsulphonyl-pyridinealdoxime derivatives, useful as fungicides
US4766136A (en)	1988-08-23	Phenylsulphonyl-pyridine aldoximes as fungicides