DE69906170T2 - Ungesättigte Oxim-Ether und ihre Verwendung als Fungizide oder Insectizide - Google Patents
Ungesättigte Oxim-Ether und ihre Verwendung als Fungizide oder InsectizideInfo
- Publication number
- DE69906170T2 DE69906170T2 DE69906170T DE69906170T DE69906170T2 DE 69906170 T2 DE69906170 T2 DE 69906170T2 DE 69906170 T DE69906170 T DE 69906170T DE 69906170 T DE69906170 T DE 69906170T DE 69906170 T2 DE69906170 T2 DE 69906170T2
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- methyl
- chlorophenyl
- compound
- compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- -1 oxime ethers Chemical class 0.000 title claims description 69
- 239000000417 fungicide Substances 0.000 title description 15
- 239000002917 insecticide Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 113
- 239000000203 mixture Substances 0.000 claims description 76
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 230000000855 fungicidal effect Effects 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 241000238631 Hexapoda Species 0.000 claims description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 6
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 5
- 241000233866 Fungi Species 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000004970 halomethyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 230000003032 phytopathogenic effect Effects 0.000 claims 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical group C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 101100311330 Schizosaccharomyces pombe (strain 972 / ATCC 24843) uap56 gene Proteins 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 101150018444 sub2 gene Proteins 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 73
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 65
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Substances [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 241000196324 Embryophyta Species 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 32
- 150000002923 oximes Chemical class 0.000 description 31
- 235000019439 ethyl acetate Nutrition 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
- 201000010099 disease Diseases 0.000 description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 19
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 240000008067 Cucumis sativus Species 0.000 description 16
- 239000000725 suspension Substances 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 13
- 241000209140 Triticum Species 0.000 description 13
- 235000021307 Triticum Nutrition 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- WTDHULULXKLSOZ-UHFFFAOYSA-N hydroxylamine hydrochloride Substances Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 10
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 238000005507 spraying Methods 0.000 description 10
- 241000221785 Erysiphales Species 0.000 description 9
- 150000002576 ketones Chemical class 0.000 description 9
- 239000012043 crude product Substances 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- 229920001817 Agar Polymers 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 241000607479 Yersinia pestis Species 0.000 description 7
- 239000008272 agar Substances 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 7
- 230000002538 fungal effect Effects 0.000 description 7
- 230000000749 insecticidal effect Effects 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 6
- 240000007594 Oryza sativa Species 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 230000003902 lesion Effects 0.000 description 6
- YOUBYEFJHQOASU-UHFFFAOYSA-N n-[4-(4-chlorophenyl)but-3-en-2-ylidene]hydroxylamine Chemical compound ON=C(C)C=CC1=CC=C(Cl)C=C1 YOUBYEFJHQOASU-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 239000000575 pesticide Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 240000005979 Hordeum vulgare Species 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 241000233679 Peronosporaceae Species 0.000 description 4
- 241000256248 Spodoptera Species 0.000 description 4
- 240000006365 Vitis vinifera Species 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- MGUDGDSNHPKOLL-DHZHZOJOSA-N methyl (e)-2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoate Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1CBr MGUDGDSNHPKOLL-DHZHZOJOSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- 241000239290 Araneae Species 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 241000462639 Epilachna varivestis Species 0.000 description 3
- 240000003768 Solanum lycopersicum Species 0.000 description 3
- 240000006677 Vicia faba Species 0.000 description 3
- 241000219094 Vitaceae Species 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 235000021021 grapes Nutrition 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 239000002054 inoculum Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical group ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 3
- 238000003359 percent control normalization Methods 0.000 description 3
- 239000001965 potato dextrose agar Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229960001866 silicon dioxide Drugs 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- FBHJUBAMBPQURB-GXDHUFHOSA-N (2e)-2-[2-(bromomethyl)phenyl]-2-methoxyimino-n-methylacetamide Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1CBr FBHJUBAMBPQURB-GXDHUFHOSA-N 0.000 description 2
- FHDSETHROOWFCQ-VOTSOKGWSA-N (e)-4-(2-chlorophenyl)but-3-en-2-one Chemical compound CC(=O)\C=C\C1=CC=CC=C1Cl FHDSETHROOWFCQ-VOTSOKGWSA-N 0.000 description 2
- WIFIQCQDQCBMCM-AATRIKPKSA-N (e)-4-[3-(trifluoromethyl)phenyl]but-3-en-2-one Chemical compound CC(=O)\C=C\C1=CC=CC(C(F)(F)F)=C1 WIFIQCQDQCBMCM-AATRIKPKSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- IXOKEPVAYTWJGM-UHFFFAOYSA-N 4-(4-fluorophenyl)but-3-en-2-one Chemical compound CC(=O)C=CC1=CC=C(F)C=C1 IXOKEPVAYTWJGM-UHFFFAOYSA-N 0.000 description 2
- 244000105624 Arachis hypogaea Species 0.000 description 2
- 241001465180 Botrytis Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 235000009849 Cucumis sativus Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 244000070406 Malus silvestris Species 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 241000736122 Parastagonospora nodorum Species 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 241000233622 Phytophthora infestans Species 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241001361634 Rhizoctonia Species 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 235000010749 Vicia faba Nutrition 0.000 description 2
- 235000002098 Vicia faba var. major Nutrition 0.000 description 2
- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 238000007098 aminolysis reaction Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 238000000889 atomisation Methods 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000004464 cereal grain Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000007799 cork Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- JYIMWRSJCRRYNK-UHFFFAOYSA-N dialuminum;disodium;oxygen(2-);silicon(4+);hydrate Chemical compound O.[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Na+].[Na+].[Al+3].[Al+3].[Si+4] JYIMWRSJCRRYNK-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 231100000162 fungitoxic Toxicity 0.000 description 2
- 230000002464 fungitoxic effect Effects 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- LDPXOYHMGOQPIV-UHFFFAOYSA-N methyl 2-[2-(bromomethyl)phenyl]-2-methoxyiminoacetate Chemical compound CON=C(C(=O)OC)C1=CC=CC=C1CBr LDPXOYHMGOQPIV-UHFFFAOYSA-N 0.000 description 2
- YCINJZQUXAFTQD-UHFFFAOYSA-N methyl 2-methoxyimino-2-(2-methylphenyl)acetate Chemical compound CON=C(C(=O)OC)C1=CC=CC=C1C YCINJZQUXAFTQD-UHFFFAOYSA-N 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 239000003595 mist Substances 0.000 description 2
- DYFFBPZIESJFJI-UHFFFAOYSA-N n-[4-(2-chlorophenyl)but-3-en-2-ylidene]hydroxylamine Chemical compound ON=C(C)C=CC1=CC=CC=C1Cl DYFFBPZIESJFJI-UHFFFAOYSA-N 0.000 description 2
- APCBJCFILSRMRW-UHFFFAOYSA-N n-[4-(4-fluorophenyl)but-3-en-2-ylidene]hydroxylamine Chemical compound ON=C(C)C=CC1=CC=C(F)C=C1 APCBJCFILSRMRW-UHFFFAOYSA-N 0.000 description 2
- MYXCASUCULWASL-UHFFFAOYSA-N n-[4-[3-(trifluoromethyl)phenyl]but-3-en-2-ylidene]hydroxylamine Chemical compound ON=C(C)C=CC1=CC=CC(C(F)(F)F)=C1 MYXCASUCULWASL-UHFFFAOYSA-N 0.000 description 2
- AMZORBZSQRUXNC-UHFFFAOYSA-N o-Tolyl acetate Chemical compound CC(=O)OC1=CC=CC=C1C AMZORBZSQRUXNC-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 235000020232 peanut Nutrition 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 231100000167 toxic agent Toxicity 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
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- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007164 v-8 juice agar Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
-
- 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
- A01N37/36—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
-
- 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
-
- 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
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- C07C251/60—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Furan Compounds (AREA)
Claims (10)
1. Verbindung der Formel:
worin
X N oder CH ist; Y O, S oder NR&sub6; ist;
A Wasserstoff, Halogen, Cyano, (C&sub1;-C&sub1;&sub2;)Alkyl oder (C&sub1;-C&sub1;&sub2;)Alkoxy ist;
R&sub1; und R&sub6; unabhängig Wasserstoff oder (C&sub1;-C&sub4;)Alkyl sind;
R&sub2; Wasserstoff, (C&sub1;-C&sub1;&sub2;)Alkyl, Halo(C&sub1;-C&sub1;&sub2;)Alkyl, (C&sub3;-C&sub7;)Cycloalkyl, (C&sub2;-
C&sub8;)-Alkenyl, Halo(C&sub2;-C&sub8;)Alkenyl, (C&sub2;-C&sub8;)Alkinyl, Halo(C&sub2;-C&sub8;)Alkinyl, Aryl
oder Aralkyl ist;
worin die oben genannten (C&sub1;-C&sub4;)Alkyl-, (C&sub1;-C&sub1;&sub2;)Alkyl-, (C&sub2;-C&sub8;)Alkenyl, (C&sub2;-
C&sub8;)Alkinyl- und (C&sub2;-C&sub8;)Cycloalkyl-Gruppen optional substituiert sein
können mit bis zu drei Substituenten, ausgewählt aus der Gruppe,
bestehend aus Nitro, Halomethyl, (C&sub1;-C&sub4;)Alkoxycarbonyl und Cyano und
worin der Ausdruck Alkyl sowohl verzweigte als auch geradkettige
Alkylkgruppen mit von 1 bis 12 Kohlenstoffatomen umfasst, und der
Ausdruck Alkenyl eine ethylenisch ungesättigte Kohlenwasserstoffgruppe,
gerad- oder verzweigtkettig, mit einer Kettenlänge von 2 bis 8
Kohlenstoffatomen und 1 oder 2 ethylenischen Bindungen betrifft, der
Ausdruck Alkinyl eine ungesättigte Kohlenwasserstoffgruppe, gerad- oder
verzweigtkettig, mit einer Kettenlänge von 2 bis 12 Kohlenstoffatomen und
1 oder 2 acetylenischen Bindungen betrifft, und der Ausdruck Arylphenyl
oder Naphthyl umfasst, welche substituiert sein können mit bis zu drei
Substituenten, unabhängig ausgewählt aus der Gruppe, bestehend aus
Halogen, Cyano, Trihalomethyl, Phenyl, Phenoxy, (C&sub1;-C&sub3;)Alkyl, (C&sub1;-
C&sub4;)Alkylthio, (C&sub1;-C&sub4;)Alkylsulfoxid und Halo(C&sub1;-C&sub4;)Alkyl und worin der
Ausdruck Aralkyl verwendet wird, um eine Gruppe zu beschreiben, worin
die Alkylkette von 1 bis 10 Kohlenstoffatomen aufweist und verzweigt oder
geradkettig sein kann;
R&sub2; Wasserstoff ist;
R&sub4; Phenyl ist, das substituiert ist mit bis zu drei Substituenten, unabhängig
ausgewählt aus der Gruppe, bestehend aus Halogen, Trihalomethyl und
Halo(C&sub1;-C&sub4;)Alkyl, und R&sub5; Wasserstoff ist, und Enantiomere, Stereoisomere
und landwirtschaftlich verträgliche Salze davon.
2. Verbindung nach Anspruch 1, X CH ist, Y O ist, R&sub2; (C&sub1;-C&sub1;&sub2;)Alkyl ist.
3. Verbindung nach Anspruch 2, worin R&sub4; ausgewählt ist aus der Gruppe,
bestehend aus 2-Chlorphenyl, 2-Fluorphenyl, 2-Trifluormethylphenyl, 3-
Chlorphenyl, 3-Fluorphenyl, 3-Trifluormethylphenyl, 4-Chlorphenyl, 4-
Fluorphenyl, 4-Trifluormethylphenyl und 2,4-Dichlorphenyl.
4. Verbindung nach Anspruch 1, worin X N ist, Y O oder NH ist, R&sub2; (C&sub1;-C&sub1;&sub2;)-
Alkyl ist.
5. Verbindung nach Anspruch 4, worin R&sub4; ausgewählt ist aus der Gruppe,
bestehend aus 2-Chlorphenyl, 2-Fluorphenyl, 2-Trifluormethylphenyl, 3-
Chlorphenyl, 3-Fluorphenyl, 3-Trifluormethylphenyl, 4-Chlorphenyl, 4-
Fluorphenyl, 4-Trifluormethylphenyl und 2,4-Dichlorphenyl.
6. Verbindung nach Anspruch 1, worin die Verbindung Methyl-3-methoxy-2-
[2-((((1-methyl-3-(2'-chlorphenyl)-2-
propenyliden)amino)oxy)methyl)phenyl]propenoat ist.
7. Verbindung nach Anspruch 1, worin die Verbindung
Methyl-3-methoxy-2-
[2-((((1-methyl-3-(4'chlorphenyl)-2-
propenyliden)amino)oxy)methyl)phenyl]propenoat ist.
8. Fungizide Zusammensetzung zum Bekämpfen phytopathogener Pilze,
umfassend einen landwirtschaftlich verträglichen Träger und die
Verbindung von Anspruch 1, worin das Verhältnis der Verbindung zu dem
Träger zwischen 99 : 1 und 1 : 4 ist.
9. Verfahren zum Bekämpfen phytopathogener Pilze, umfassend das
Anwenden der Verbindung nach Anspruch 1 in einer Menge von 0,005 bis
50 Kilogramm pro Hektar auf den Ort, an welchem eine Bekämpfung
gewünscht ist.
10. Verfahren zum Bekämpfen von Insekten, umfassend das Anwenden einer
Menge von 0,0005 bis 10 Kilogramm pro Hektar der Verbindung nach
Anspruch 1 auf den Lebensraum der Insekten.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN98113756A CN1062711C (zh) | 1998-02-10 | 1998-02-10 | 不饱和肟醚类杀虫、杀真菌剂 |
US10601398P | 1998-10-28 | 1998-10-28 |
Publications (2)
Publication Number | Publication Date |
---|---|
DE69906170D1 DE69906170D1 (de) | 2003-04-30 |
DE69906170T2 true DE69906170T2 (de) | 2003-10-23 |
Family
ID=25744701
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE69906170T Expired - Lifetime DE69906170T2 (de) | 1998-02-10 | 1999-01-26 | Ungesättigte Oxim-Ether und ihre Verwendung als Fungizide oder Insectizide |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0936213B1 (de) |
JP (1) | JPH11315057A (de) |
KR (1) | KR19990046320A (de) |
AU (1) | AU1544899A (de) |
BR (1) | BR9900561A (de) |
DE (1) | DE69906170T2 (de) |
Families Citing this family (43)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6303818B1 (en) * | 2000-08-08 | 2001-10-16 | Dow Agrosciences Llc | Unsaturated oxime ethers and their use as fungicides |
KR100379761B1 (ko) * | 2000-11-23 | 2003-04-11 | 한국화학연구원 | 옥심기를 측쇄로 하는 신규의 프로페노익 에스테르 및아미드 유도체, 이의 제조방법 그리고 이를 함유하는살균제 조성물 |
CN1293046C (zh) * | 2003-08-12 | 2007-01-03 | 沈阳化工研究院 | 具有杀真菌、杀虫活性的不饱和肟醚类化合物 |
US7601673B2 (en) | 2004-04-30 | 2009-10-13 | Basf Aktiengesellschaft | Fungicidal mixtures |
GB0418047D0 (en) | 2004-08-12 | 2004-09-15 | Syngenta Participations Ag | Fungicidal compositions |
GB0422401D0 (en) | 2004-10-08 | 2004-11-10 | Syngenta Participations Ag | Fungicidal compositions |
PE20060801A1 (es) * | 2004-12-23 | 2006-10-03 | Basf Ag | Mezclas fungicidas |
BRPI0519234A2 (pt) * | 2004-12-23 | 2009-01-06 | Basf Ag | misturas fungicidas para combater fungos nocivos fitopatogÊnicos, agente, processo para combater fungos nocivos fitopatogÊnicos, sementes, e, uso dos compostos |
CA2590364A1 (en) * | 2004-12-23 | 2006-07-06 | Basf Aktiengesellschaft | Fungicidal mixtures |
JP2008525348A (ja) * | 2004-12-23 | 2008-07-17 | ビーエーエスエフ ソシエタス・ヨーロピア | 殺菌剤混合物 |
WO2006069701A1 (de) * | 2004-12-23 | 2006-07-06 | Basf Aktiengesellschaft | Fungizide mischungen enthaltend enestroburin und mindestens einen wirkstoff der gruppe der azole |
WO2006069698A1 (de) * | 2004-12-23 | 2006-07-06 | Basf Aktiengesellschaft | Fungizide mischungen |
WO2006125637A1 (en) * | 2005-05-25 | 2006-11-30 | Basf Aktiengesellschaft | O-(phenyl/heterocyclyl)methyl oxime ether compounds for combating animal pests |
JP5101496B2 (ja) | 2005-06-09 | 2012-12-19 | バイエル・クロップサイエンス・アーゲー | 活性物質の組み合わせ |
DE102005026482A1 (de) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Wirkstoffkombinationen |
US7807714B2 (en) | 2006-02-09 | 2010-10-05 | Syngenta Crop Protection, Inc. | Fungicidal compositions |
NZ589395A (en) | 2007-04-25 | 2011-04-29 | Syngenta Participations Ag | Fungicidal compositions containing cyprodinil and a benzonobornene amide derivative useful for controlling diseases on plants caused by phytopathogens |
US8349877B2 (en) | 2007-09-26 | 2013-01-08 | Basf Se | Ternary fungicidal compositions comprising boscalid and chlorothalonil |
WO2011026796A1 (en) | 2009-09-01 | 2011-03-10 | Basf Se | Synergistic fungicidal mixtures comprising lactylates and method for combating phytopathogenic fungi |
CN102741233A (zh) | 2010-02-04 | 2012-10-17 | 先正达参股股份有限公司 | 哒嗪衍生物,制备它们的方法以及它们作为杀真菌剂的用途 |
EP2539338A1 (de) | 2010-02-24 | 2013-01-02 | Syngenta Participations AG | Neue mikrobizide |
CN103153958A (zh) | 2010-07-02 | 2013-06-12 | 先正达参股股份有限公司 | 新颖的杀微生物的二肟醚衍生物 |
CN102308799A (zh) * | 2010-07-02 | 2012-01-11 | 海利尔药业集团股份有限公司 | 一种含有烯肟菌酯和溴菌腈的杀菌组合物 |
TW201211005A (en) | 2010-07-29 | 2012-03-16 | Syngenta Participations Ag | Novel microbiocidal dioxime ether derivatives |
AR083112A1 (es) | 2010-10-01 | 2013-01-30 | Syngenta Participations Ag | Metodo para controlar enfermedades fitopatogenas y composiciones fungicidas utiles para dicho control |
WO2012066122A1 (en) | 2010-11-18 | 2012-05-24 | Syngenta Participations Ag | 2 - (pyridin- 2 -yl) -quinazoline derivatives and their use as microbicides |
WO2012069652A2 (en) | 2010-11-26 | 2012-05-31 | Syngenta Participations Ag | Fungicide mixtures |
EP2481284A3 (de) | 2011-01-27 | 2012-10-17 | Basf Se | Pestizidgemische |
JP6049684B2 (ja) | 2011-03-23 | 2016-12-21 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | イミダゾリウム基を含むポリマーのイオン性化合物を含有する組成物 |
CN102204552A (zh) * | 2011-04-09 | 2011-10-05 | 陕西汤普森生物科技有限公司 | 一种含烯肟菌酯与抗生素类化合物的杀菌组合物 |
JP5997931B2 (ja) * | 2011-05-25 | 2016-09-28 | 石原産業株式会社 | 農園芸用殺菌剤組成物及び植物病害の防除方法 |
WO2013011010A1 (en) | 2011-07-19 | 2013-01-24 | Syngenta Participations Ag | Fungizide mixtures |
AR087609A1 (es) | 2011-08-23 | 2014-04-03 | Syngenta Participations Ag | Microbiocidas |
US20150257383A1 (en) | 2012-10-12 | 2015-09-17 | Basf Se | Method for combating phytopathogenic harmful microbes on cultivated plants or plant propagation material |
CN105050406B (zh) | 2012-12-20 | 2017-09-15 | 巴斯夫农业公司 | 包含三唑化合物的组合物 |
EP2783569A1 (de) | 2013-03-28 | 2014-10-01 | Basf Se | Zusammensetzungen mit einer Triazol-Verbindung |
EP2835052A1 (de) | 2013-08-07 | 2015-02-11 | Basf Se | Fungizide Mischungen mit Pyrimidinfungiziden |
CN105722833A (zh) | 2013-09-16 | 2016-06-29 | 巴斯夫欧洲公司 | 杀真菌的嘧啶化合物 |
WO2015036059A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
WO2015119099A1 (ja) * | 2014-02-05 | 2015-08-13 | 日本曹達株式会社 | ピリジン化合物およびその用途 |
CN106132202B (zh) | 2014-03-20 | 2021-12-31 | 三井化学Agro株式会社 | 植物病害防除组合物及应用该组合物以防除植物病害的方法 |
EP2979549A1 (de) | 2014-07-31 | 2016-02-03 | Basf Se | Verfahren zur verbesserung der gesundheit einer pflanze |
EP3209818B1 (de) | 2014-10-24 | 2019-12-11 | Basf Se | Organische pestizid-teilchen |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0506149B1 (de) * | 1988-11-21 | 1998-08-12 | Zeneca Limited | Zwischenverbindungen zur Herstellung von Fungiziden |
KR100187541B1 (ko) * | 1988-12-29 | 1999-06-01 | 쟝-자크 오가이; 롤란트 보러 | 알디미노-또는 케티미노-옥시-오르토-톨릴아크릴산의 메틸 에스테르,이의 제조방법 및 이를 함유하는 살진균제 |
PH11991042549B1 (de) * | 1990-06-05 | 2000-12-04 | ||
ES2120100T3 (es) * | 1990-06-27 | 1998-10-16 | Basf Ag | O-bencil-oximeteres y agentes protectores de las plantas que contienen estos compuestos. |
WO1992013830A1 (en) * | 1991-01-30 | 1992-08-20 | Zeneca Limited | Fungicides |
CH686307A5 (de) * | 1991-04-19 | 1996-02-29 | Ciba Geigy Ag | Oximether des 3-Methoxy-2-(o-tolyl)acrylsouremethylesters, Verfahren zu ihrer Herstellung und fungizide Mittel, die diese als Wirkstoffe enthalten. |
-
1999
- 1999-01-26 DE DE69906170T patent/DE69906170T2/de not_active Expired - Lifetime
- 1999-01-26 EP EP99300573A patent/EP0936213B1/de not_active Expired - Lifetime
- 1999-02-05 AU AU15448/99A patent/AU1544899A/en not_active Abandoned
- 1999-02-09 BR BR9900561-1A patent/BR9900561A/pt not_active Application Discontinuation
- 1999-02-10 KR KR1019990004554A patent/KR19990046320A/ko not_active Application Discontinuation
- 1999-02-10 JP JP11032340A patent/JPH11315057A/ja not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
DE69906170D1 (de) | 2003-04-30 |
AU1544899A (en) | 1999-08-26 |
BR9900561A (pt) | 2000-05-16 |
KR19990046320A (ko) | 1999-07-05 |
EP0936213B1 (de) | 2003-03-26 |
EP0936213A1 (de) | 1999-08-18 |
JPH11315057A (ja) | 1999-11-16 |
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