SK20295A3 - O-benzyl oxime ether derivatives and their use as recticides and their use - Google Patents
O-benzyl oxime ether derivatives and their use as recticides and their use Download PDFInfo
- Publication number
- SK20295A3 SK20295A3 SK202-95A SK20295A SK20295A3 SK 20295 A3 SK20295 A3 SK 20295A3 SK 20295 A SK20295 A SK 20295A SK 20295 A3 SK20295 A3 SK 20295A3
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- Slovakia
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- carbon atoms
- phenyl
- alkyl
- alkoxy
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- -1 O-benzyl oxime ether derivatives Chemical class 0.000 title claims abstract description 454
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 161
- 239000000203 mixture Substances 0.000 claims abstract description 64
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 62
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 26
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 19
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 13
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 9
- 239000011593 sulfur Chemical group 0.000 claims abstract description 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 8
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 150000001721 carbon Chemical group 0.000 claims abstract description 4
- 244000005700 microbiome Species 0.000 claims abstract description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 81
- 125000000217 alkyl group Chemical group 0.000 claims description 73
- 239000004480 active ingredient Substances 0.000 claims description 42
- 125000003545 alkoxy group Chemical group 0.000 claims description 41
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 206010061217 Infestation Diseases 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 14
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 14
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 239000000460 chlorine Chemical group 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- 239000004094 surface-active agent Substances 0.000 claims description 9
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 8
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 229910052801 chlorine Chemical group 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 150000002825 nitriles Chemical class 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 7
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 7
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 6
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000005605 benzo group Chemical group 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
- 150000001409 amidines Chemical class 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 4
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- QTAAKTRBARVAQY-UHFFFAOYSA-N 3,6-dihydro-2h-1,4-thiazine Chemical group C1CN=CCS1 QTAAKTRBARVAQY-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- RLECCBFNWDXKPK-UHFFFAOYSA-N bis(trimethylsilyl)sulfide Chemical compound C[Si](C)(C)S[Si](C)(C)C RLECCBFNWDXKPK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 2
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims description 2
- 230000000361 pesticidal effect Effects 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
- 230000001902 propagating effect Effects 0.000 claims description 2
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 claims description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims 2
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 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 claims 1
- USVZHTBPMMSRHY-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-chlorophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Cl USVZHTBPMMSRHY-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 1
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 1
- 125000000262 haloalkenyl group Chemical group 0.000 claims 1
- 125000000232 haloalkynyl group Chemical group 0.000 claims 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 83
- 150000002431 hydrogen Chemical group 0.000 abstract 6
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 abstract 4
- BGCPLWWYPZAURQ-UHFFFAOYSA-N 5-[[5-chloro-2-(2,2,6,6-tetramethylmorpholin-4-yl)pyrimidin-4-yl]amino]-3-(3-hydroxy-3-methylbutyl)-1-methylbenzimidazol-2-one Chemical group ClC=1C(=NC(=NC=1)N1CC(OC(C1)(C)C)(C)C)NC1=CC2=C(N(C(N2CCC(C)(C)O)=O)C)C=C1 BGCPLWWYPZAURQ-UHFFFAOYSA-N 0.000 abstract 1
- 229910007161 Si(CH3)3 Inorganic materials 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 70
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- 238000001819 mass spectrum Methods 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 239000002585 base Substances 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 239000007921 spray Substances 0.000 description 26
- 239000000725 suspension Substances 0.000 description 24
- 239000003921 oil Substances 0.000 description 23
- 235000019198 oils Nutrition 0.000 description 23
- 230000002538 fungal effect Effects 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 239000002689 soil Substances 0.000 description 19
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 239000000126 substance Substances 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 241000233866 Fungi Species 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 240000007594 Oryza sativa Species 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
- 239000013543 active substance Substances 0.000 description 11
- 208000015181 infectious disease Diseases 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 230000001681 protective effect Effects 0.000 description 9
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 8
- 241000209140 Triticum Species 0.000 description 8
- 235000013339 cereals Nutrition 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000004949 mass spectrometry Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 6
- 240000005979 Hordeum vulgare Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 230000003032 phytopathogenic effect Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 230000009885 systemic effect Effects 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 239000004563 wettable powder Substances 0.000 description 6
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 5
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 5
- 239000005995 Aluminium silicate Substances 0.000 description 5
- 235000011430 Malus pumila Nutrition 0.000 description 5
- 244000070406 Malus silvestris Species 0.000 description 5
- 235000015103 Malus silvestris Nutrition 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 235000012211 aluminium silicate Nutrition 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 238000011534 incubation Methods 0.000 description 5
- 230000003902 lesion Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 4
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 4
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 235000007238 Secale cereale Nutrition 0.000 description 4
- 244000082988 Secale cereale Species 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 240000003768 Solanum lycopersicum Species 0.000 description 4
- 235000021536 Sugar beet Nutrition 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 150000003556 thioamides Chemical class 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- AICIYIDUYNFPRY-UHFFFAOYSA-N 1,3-dihydro-2H-imidazol-2-one Chemical compound O=C1NC=CN1 AICIYIDUYNFPRY-UHFFFAOYSA-N 0.000 description 3
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 3
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 3
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- FHYUCVWDMABHHH-UHFFFAOYSA-N toluene;1,2-xylene Chemical compound CC1=CC=CC=C1.CC1=CC=CC=C1C FHYUCVWDMABHHH-UHFFFAOYSA-N 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- FUWRUKKMVOFCBV-UHFFFAOYSA-L trisodium;carbonate Chemical compound [Na+].[Na+].[Na+].[O-]C([O-])=O FUWRUKKMVOFCBV-UHFFFAOYSA-L 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 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
- 235000020234 walnut Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 241000228158 x Triticosecale Species 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic 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
- 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
- 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
- A01N37/52—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 groups, e.g. carboxylic acid amidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/62—Carboxylic acid nitriles containing cyano groups and oxygen atoms being part of oxyimino groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/04—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines without replacement of the other oxygen atom of the carboxyl group, e.g. imino-ethers
- C07C257/06—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines without replacement of the other oxygen atom of the carboxyl group, e.g. imino-ethers having carbon atoms of imino-carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms, or to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/14—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/10—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
- C07C259/14—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
- C07C259/20—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines with at least one nitrogen atom of hydroxamidine groups bound to another nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/62—Compounds containing any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylcarbamates
- C07C271/64—Y being a hydrogen or a carbon atom, e.g. benzoylcarbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/40—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C327/44—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/58—Derivatives of thiocarboxylic acids, the doubly-bound oxygen atoms being replaced by nitrogen atoms, e.g. imino-thio ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
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- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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CH151693 | 1993-05-18 | ||
PCT/EP1994/001457 WO1994026700A1 (en) | 1993-05-18 | 1994-05-06 | O-benzyl oxime ether derivatives and their use as pesticides |
Publications (1)
Publication Number | Publication Date |
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SK20295A3 true SK20295A3 (en) | 1995-07-11 |
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ID=4212273
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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SK202-95A SK20295A3 (en) | 1993-05-18 | 1994-05-06 | O-benzyl oxime ether derivatives and their use as recticides and their use |
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US (2) | US6211240B1 (cs) |
EP (1) | EP0651737B1 (cs) |
JP (1) | JP3704649B2 (cs) |
KR (1) | KR950702524A (cs) |
CN (1) | CN1109686A (cs) |
AT (1) | ATE168993T1 (cs) |
AU (1) | AU685464B2 (cs) |
BR (1) | BR9405370A (cs) |
CA (1) | CA2138166A1 (cs) |
CZ (1) | CZ41195A3 (cs) |
DE (1) | DE69412033T2 (cs) |
DK (1) | DK0651737T3 (cs) |
ES (1) | ES2119202T3 (cs) |
GR (1) | GR3027578T3 (cs) |
HU (1) | HUT69038A (cs) |
IL (1) | IL109660A0 (cs) |
LT (1) | LT3262B (cs) |
NO (1) | NO950168L (cs) |
NZ (1) | NZ267074A (cs) |
PL (1) | PL175820B1 (cs) |
RO (1) | RO111188B1 (cs) |
RU (1) | RU95105988A (cs) |
SG (1) | SG44594A1 (cs) |
SK (1) | SK20295A3 (cs) |
TW (1) | TW299310B (cs) |
WO (1) | WO1994026700A1 (cs) |
Families Citing this family (31)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0656352A1 (de) * | 1993-12-03 | 1995-06-07 | BASF Aktiengesellschaft | Thioimidate als Mittel gegen tierische Schädlinge und Schadpilze |
EP0741694B1 (de) * | 1994-02-04 | 2003-04-02 | Basf Aktiengesellschaft | Phenylessigsäurederivate, verfahren und zwischenprodukte zu ihrer herstellung und sie enthaltende mittel |
EP0779884B1 (de) | 1994-09-09 | 2000-05-03 | Bayer Ag | Imidsäurederivate und ihre verwendung als schädlingsbekämpfungsmittel |
US5977182A (en) * | 1994-11-17 | 1999-11-02 | Novartis Finance Corporation | O-benzyl oxime ether derivatives and their use as pesticides |
IL115894A0 (en) * | 1994-12-08 | 1996-01-31 | Du Pont | Organosilanes and organogermanes and their use |
MX9705726A (es) * | 1995-01-30 | 1997-11-29 | Bayer Ag | Amidas del acido alcoximinoacetico. |
KR100420658B1 (ko) * | 1995-01-30 | 2004-07-23 | 바이엘 악티엔게젤샤프트 | 알콕스이미노아세트산아미드 |
AU6354896A (en) * | 1995-06-21 | 1997-01-22 | Ciba-Geigy Ag | Thioamides s-oxides for use as pesticides |
DE19540388A1 (de) | 1995-10-30 | 1997-05-07 | Hoechst Ag | Neuartige Glycomimetika als Selektin-Antagonisten und entzündungshemmend wirkende Arzneimittel |
WO1997047592A1 (en) * | 1996-06-12 | 1997-12-18 | Novartis Ag | Pesticides |
DE59707658D1 (de) | 1996-07-22 | 2002-08-08 | Bayer Ag | Glyoxylsäure-derivate |
TR199700975A2 (xx) * | 1996-09-27 | 1998-04-21 | Novartis Ag | Salg�n hastal�k ila�lar� (pepticides). |
AU6811698A (en) * | 1996-10-23 | 1998-05-15 | Novartis Ag | Pesticides |
CN1099408C (zh) * | 1998-10-07 | 2003-01-22 | 湖南化工研究院 | 杀生物的肟醚类化合物 |
US6350381B2 (en) * | 1998-10-27 | 2002-02-26 | Kinder Morgan Energy Partners, L.P. | Biodegradation of ethers using fatty acid enhanced microbes |
EP1125931A1 (en) * | 2000-02-17 | 2001-08-22 | Hunan Research Institute of Chemical Industry | Biocidal alkyl-substituted-(hetero)aryl-ketoxime-O-ethers and the production method thereof |
WO2008143969A1 (en) * | 2007-05-18 | 2008-11-27 | Valent Biosciences Corporation | Oil formulations and methods of use |
CN102911093B (zh) * | 2012-10-25 | 2014-08-13 | 湖南化工研究院 | 一种硫氟肟醚的制备方法 |
US20180141897A1 (en) | 2014-12-08 | 2018-05-24 | The Research Foundation For The State University Of New York | Anti-fungals targeting the synthesis of fungal shingolipids |
US10544092B2 (en) | 2015-12-25 | 2020-01-28 | Shenyang Sinochem Agrochemicals R&D Co., Ltd. | Malononitrile oxime ether compound and use thereof |
WO2018232298A1 (en) | 2017-06-16 | 2018-12-20 | The Research Foundation For The State University Of New York | Anti-fungals compounds targeting the synthesis of fungal sphingolipids |
CN112189665B (zh) * | 2019-07-08 | 2022-03-22 | 沈阳中化农药化工研发有限公司 | 一种杀真菌细菌组合物和应用 |
CN112189660B (zh) * | 2019-07-08 | 2022-03-08 | 沈阳中化农药化工研发有限公司 | 杀真菌、细菌组合物及其应用 |
CN112189669B (zh) * | 2019-07-08 | 2022-03-08 | 沈阳中化农药化工研发有限公司 | 杀真菌、细菌组合物和应用 |
CN112189663B (zh) * | 2019-07-08 | 2022-03-22 | 沈阳中化农药化工研发有限公司 | 一种杀真菌、细菌组合物和应用 |
WO2021004195A1 (zh) * | 2019-07-08 | 2021-01-14 | 沈阳中化农药化工研发有限公司 | 杀真菌、细菌组合物及应用 |
CN112189661B (zh) * | 2019-07-08 | 2022-03-29 | 沈阳中化农药化工研发有限公司 | 杀真菌、细菌组合物及应用 |
CN112189662B (zh) * | 2019-07-08 | 2022-03-08 | 沈阳中化农药化工研发有限公司 | 杀真菌、细菌组合物及其应用 |
CN112189668B (zh) * | 2019-07-08 | 2022-03-08 | 沈阳中化农药化工研发有限公司 | 一种杀真菌、细菌组合物及应用 |
CN114532346B (zh) * | 2020-11-19 | 2023-07-07 | 沈阳中化农药化工研发有限公司 | 一种杀真菌、细菌组合物及应用 |
CN115124481A (zh) * | 2022-07-08 | 2022-09-30 | 中国农业大学 | 一种丙二腈肟醚类化合物及其制备方法与应用 |
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DE3817280A1 (de) | 1988-05-20 | 1989-11-30 | Asea Brown Boveri | Spulenwicklung |
AU623864B2 (en) | 1988-08-29 | 1992-05-28 | Applied Microbiology, Inc | Method of treating mastitis and other staphylococcal infections |
ATE169616T1 (de) * | 1988-11-21 | 1998-08-15 | Zeneca Ltd | Zwischenverbindungen zur herstellung von fungiziden |
DK0629609T3 (da) * | 1989-05-17 | 1996-12-23 | Shionogi & Co | Fremgangsmåde til fremstilling af alkoxyiminoacetamidderivater og et mellemprodukt dertil |
DE3938140A1 (de) | 1989-11-16 | 1991-08-08 | Beiersdorf Ag | Desodorierende kosmetische mittel |
ES2110421T5 (es) * | 1990-06-27 | 2004-12-01 | Basf Aktiengesellschaft | O-bencil-oximeteres y los agentes protectores de las plantas que contienen estos compuestos. |
JPH06504538A (ja) * | 1991-01-30 | 1994-05-26 | ゼネカ・リミテッド | 殺菌剤 |
DE4103695A1 (de) | 1991-02-07 | 1992-08-13 | Basf Ag | Oximether und diese enthaltende fungizide |
JP3188286B2 (ja) * | 1991-08-20 | 2001-07-16 | 塩野義製薬株式会社 | フェニルメトキシイミノ化合物およびそれを用いる農業用殺菌剤 |
JPH05201946A (ja) * | 1992-01-27 | 1993-08-10 | Mitsubishi Kasei Corp | メトキシイミノ酢酸誘導体およびこれを有効成分とする農園芸用殺菌剤 |
JPH05294948A (ja) * | 1992-04-18 | 1993-11-09 | Nippon Nohyaku Co Ltd | N−(置換ベンジルオキシ)イミン誘導体及びその製造方法並びに農園芸用殺菌剤 |
IL107690A (en) | 1992-12-14 | 1997-09-30 | Basf Ag | 2, a-DISUBSTITUTED BENZENEACETOTHIOAMIDES, THEIR PREPARATION AND THEIR USE AS PESTICIDES AND FUNGICIDES |
-
1994
- 1994-05-04 TW TW083104019A patent/TW299310B/zh active
- 1994-05-06 DK DK94917585T patent/DK0651737T3/da active
- 1994-05-06 AT AT94917585T patent/ATE168993T1/de not_active IP Right Cessation
- 1994-05-06 RU RU95105988/04A patent/RU95105988A/ru unknown
- 1994-05-06 KR KR1019950700209A patent/KR950702524A/ko not_active Application Discontinuation
- 1994-05-06 WO PCT/EP1994/001457 patent/WO1994026700A1/en not_active Application Discontinuation
- 1994-05-06 SK SK202-95A patent/SK20295A3/sk unknown
- 1994-05-06 HU HU9403522A patent/HUT69038A/hu unknown
- 1994-05-06 DE DE69412033T patent/DE69412033T2/de not_active Expired - Fee Related
- 1994-05-06 PL PL94307090A patent/PL175820B1/pl unknown
- 1994-05-06 AU AU69254/94A patent/AU685464B2/en not_active Ceased
- 1994-05-06 CN CN94190293A patent/CN1109686A/zh active Pending
- 1994-05-06 SG SG1996003428A patent/SG44594A1/en unknown
- 1994-05-06 EP EP94917585A patent/EP0651737B1/en not_active Expired - Lifetime
- 1994-05-06 JP JP52491794A patent/JP3704649B2/ja not_active Expired - Fee Related
- 1994-05-06 RO RO95-00051A patent/RO111188B1/ro unknown
- 1994-05-06 NZ NZ267074A patent/NZ267074A/en unknown
- 1994-05-06 ES ES94917585T patent/ES2119202T3/es not_active Expired - Lifetime
- 1994-05-06 CA CA002138166A patent/CA2138166A1/en not_active Abandoned
- 1994-05-06 CZ CZ95411A patent/CZ41195A3/cs unknown
- 1994-05-06 BR BR9405370-7A patent/BR9405370A/pt not_active Application Discontinuation
- 1994-05-11 LT LTIP1932A patent/LT3262B/lt not_active IP Right Cessation
- 1994-05-17 IL IL10966094A patent/IL109660A0/xx unknown
-
1995
- 1995-01-17 NO NO950168A patent/NO950168L/no unknown
-
1996
- 1996-10-29 US US08/739,388 patent/US6211240B1/en not_active Expired - Fee Related
-
1998
- 1998-08-04 GR GR980401764T patent/GR3027578T3/el unknown
-
2000
- 2000-09-27 US US09/671,562 patent/US6342633B1/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
EP0651737A1 (en) | 1995-05-10 |
CZ41195A3 (en) | 1995-10-18 |
BR9405370A (pt) | 1999-11-03 |
EP0651737B1 (en) | 1998-07-29 |
NO950168D0 (no) | 1995-01-17 |
CA2138166A1 (en) | 1994-11-24 |
RU95105988A (ru) | 1996-10-27 |
NO950168L (no) | 1995-03-17 |
DK0651737T3 (da) | 1999-04-26 |
IL109660A0 (en) | 1994-08-26 |
KR950702524A (ko) | 1995-07-29 |
WO1994026700A1 (en) | 1994-11-24 |
RO111188B1 (ro) | 1996-07-30 |
LT3262B (en) | 1995-05-25 |
SG44594A1 (en) | 1997-12-19 |
HUT69038A (en) | 1995-08-28 |
LTIP1932A (en) | 1994-11-25 |
AU6925494A (en) | 1994-12-12 |
TW299310B (cs) | 1997-03-01 |
NZ267074A (en) | 1997-01-29 |
CN1109686A (zh) | 1995-10-04 |
US6211240B1 (en) | 2001-04-03 |
JPH07509491A (ja) | 1995-10-19 |
DE69412033D1 (de) | 1998-09-03 |
GR3027578T3 (en) | 1998-11-30 |
ATE168993T1 (de) | 1998-08-15 |
DE69412033T2 (de) | 1999-01-07 |
PL307090A1 (en) | 1995-05-02 |
PL175820B1 (pl) | 1999-02-26 |
HU9403522D0 (en) | 1995-03-28 |
US6342633B1 (en) | 2002-01-29 |
AU685464B2 (en) | 1998-01-22 |
JP3704649B2 (ja) | 2005-10-12 |
ES2119202T3 (es) | 1998-10-01 |
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