SK88096A3 - Pesticidal compounds, preparation method thereof and intermediate products at this method and pesticidal agents containing them - Google Patents
Pesticidal compounds, preparation method thereof and intermediate products at this method and pesticidal agents containing them Download PDFInfo
- Publication number
- SK88096A3 SK88096A3 SK880-96A SK88096A SK88096A3 SK 88096 A3 SK88096 A3 SK 88096A3 SK 88096 A SK88096 A SK 88096A SK 88096 A3 SK88096 A3 SK 88096A3
- Authority
- SK
- Slovakia
- Prior art keywords
- group
- alkyl
- carbon atoms
- formula
- unsubstituted
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 188
- 238000002360 preparation method Methods 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 26
- 230000000361 pesticidal effect Effects 0.000 title abstract description 6
- 239000013067 intermediate product Substances 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 137
- 125000005843 halogen group Chemical group 0.000 claims abstract description 120
- -1 halo-C1-C4alkyl Chemical group 0.000 claims abstract description 119
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 103
- 239000000203 mixture Substances 0.000 claims abstract description 88
- 150000002367 halogens Chemical class 0.000 claims abstract description 81
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 76
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 63
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 55
- 239000004480 active ingredient Substances 0.000 claims abstract description 52
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 44
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 37
- 125000001424 substituent group Chemical group 0.000 claims abstract description 31
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 24
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 20
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 18
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 17
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 16
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 16
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 16
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 16
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 15
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 15
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 185
- 125000000217 alkyl group Chemical group 0.000 claims description 119
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 112
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 105
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 84
- 125000001188 haloalkyl group Chemical group 0.000 claims description 37
- 125000004970 halomethyl group Chemical group 0.000 claims description 37
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 17
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 16
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 239000001301 oxygen Chemical group 0.000 claims description 15
- 241000233866 Fungi Species 0.000 claims description 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
- 239000011593 sulfur Chemical group 0.000 claims description 14
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 11
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 10
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 8
- 241000238876 Acari Species 0.000 claims description 7
- 125000005038 alkynylalkyl group Chemical group 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 241000238631 Hexapoda Species 0.000 claims description 6
- 125000004946 alkenylalkyl group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- 230000003032 phytopathogenic effect Effects 0.000 claims description 6
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 5
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 5
- 150000002923 oximes Chemical class 0.000 claims description 5
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 5
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 244000005700 microbiome Species 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
- 239000003444 phase transfer catalyst Substances 0.000 claims description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 claims description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 2
- 125000002785 azepinyl group Chemical group 0.000 claims description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
- 239000012022 methylating agents Substances 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 150000003852 triazoles Chemical group 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 1
- DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 claims 1
- 229930194542 Keto Natural products 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 150000002085 enols Chemical class 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 abstract description 10
- 241000607479 Yersinia pestis Species 0.000 abstract description 6
- 230000000895 acaricidal effect Effects 0.000 abstract description 5
- 230000003641 microbiacidal effect Effects 0.000 abstract description 4
- 238000003898 horticulture Methods 0.000 abstract description 3
- 239000002917 insecticide Substances 0.000 abstract description 3
- 239000000642 acaricide Substances 0.000 abstract description 2
- 229940124561 microbicide Drugs 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 76
- 241000196324 Embryophyta Species 0.000 description 72
- 239000003921 oil Substances 0.000 description 57
- 235000019198 oils Nutrition 0.000 description 57
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000007921 spray Substances 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 239000000725 suspension Substances 0.000 description 24
- 238000012360 testing method Methods 0.000 description 23
- 230000002538 fungal effect Effects 0.000 description 21
- 239000002689 soil Substances 0.000 description 20
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- 229920005989 resin Polymers 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 206010061217 Infestation Diseases 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 14
- 240000007594 Oryza sativa Species 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- 238000011081 inoculation Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 9
- 230000001681 protective effect Effects 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 241000209140 Triticum Species 0.000 description 8
- 239000013543 active substance Substances 0.000 description 8
- 235000013339 cereals Nutrition 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 235000007164 Oryza sativa Nutrition 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 125000001841 imino group Chemical group [H]N=* 0.000 description 7
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 235000009566 rice Nutrition 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 6
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 6
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 240000005979 Hordeum vulgare Species 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 235000012211 aluminium silicate Nutrition 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 235000013399 edible fruits Nutrition 0.000 description 6
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 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 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 230000009885 systemic effect Effects 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- 239000013078 crystal Substances 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 238000011534 incubation Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 238000009331 sowing Methods 0.000 description 5
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
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- 240000003768 Solanum lycopersicum Species 0.000 description 4
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- 239000002585 base Substances 0.000 description 4
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- 239000000969 carrier Substances 0.000 description 4
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- 238000000576 coating method Methods 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
- 238000011156 evaluation Methods 0.000 description 4
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- 229910052740 iodine Inorganic materials 0.000 description 4
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- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 3
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 3
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 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 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 description 3
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- 241000335053 Beta vulgaris Species 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
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- 241000257303 Hymenoptera Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 240000006365 Vitis vinifera Species 0.000 description 3
- 235000014787 Vitis vinifera Nutrition 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
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- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
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- 239000002798 polar solvent Substances 0.000 description 1
- 229920001155 polypropylene Chemical class 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- MEGPURSNXMUDAE-RLMOJYMMSA-N scopoline Chemical compound C([C@H](O1)C2)[C@@H]3N(C)[C@H]2[C@H]1[C@H]3O MEGPURSNXMUDAE-RLMOJYMMSA-N 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
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- 238000002791 soaking Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
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- 150000003536 tetrazoles Chemical class 0.000 description 1
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- 239000002562 thickening agent Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
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- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
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- 150000003672 ureas Chemical class 0.000 description 1
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Classifications
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- 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
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
- C07D213/77—Hydrazine radicals
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- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
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- C—CHEMISTRY; METALLURGY
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
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- C07C251/76—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
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- C07C251/78—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
- C07C251/80—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/61—Carboxylic acid nitriles containing cyano groups and nitrogen atoms being part of imino groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
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- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
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- C—CHEMISTRY; METALLURGY
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- 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
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- C—CHEMISTRY; METALLURGY
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- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
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- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
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- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- 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
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1294 | 1994-01-05 | ||
CH211794 | 1994-07-01 | ||
PCT/EP1994/004318 WO1995018789A1 (en) | 1994-01-05 | 1994-12-27 | Pesticides |
US08/526,859 US5756426A (en) | 1994-01-05 | 1995-09-11 | Phenyl acetic acid derivatives as pesticides |
Publications (1)
Publication Number | Publication Date |
---|---|
SK88096A3 true SK88096A3 (en) | 1996-12-04 |
Family
ID=27171714
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK880-96A SK88096A3 (en) | 1994-01-05 | 1994-12-27 | Pesticidal compounds, preparation method thereof and intermediate products at this method and pesticidal agents containing them |
Country Status (15)
Country | Link |
---|---|
US (3) | US5756426A (ru) |
EP (1) | EP0738260B2 (ru) |
CN (1) | CN1152007C (ru) |
AP (1) | AP654A (ru) |
AU (1) | AU690190B2 (ru) |
CA (1) | CA2179418C (ru) |
CZ (1) | CZ291625B6 (ru) |
FI (1) | FI962712A (ru) |
HU (1) | HU219157B (ru) |
IL (1) | IL112227A (ru) |
LV (1) | LV11684B (ru) |
MD (1) | MD1315C2 (ru) |
NO (1) | NO307045B1 (ru) |
SK (1) | SK88096A3 (ru) |
WO (1) | WO1995018789A1 (ru) |
Families Citing this family (69)
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ATE195509T1 (de) | 1994-02-04 | 2000-09-15 | Basf Ag | Phenylessigsäurederivate, verfahren und zwischenprodukte zu ihrer herstellung und sie enthaltende mittel |
WO1995021154A2 (de) * | 1994-02-04 | 1995-08-10 | Basf Aktiengesellschaft | Phenylessigsäurederivate, verfahren und zwischenprodukte zu ihrer herstellung und sie enthaltende mittel |
CH689228A5 (de) * | 1994-10-07 | 1998-12-31 | Novartis Ag | Oximether, sowie diese enthaltende Pflanzenschutzmittel. |
MX9703616A (es) * | 1994-11-17 | 1997-08-30 | Novartis Ag | Derivados de eter de oxima o-bencilica y su uso como pesticidas. |
US5929279A (en) * | 1995-04-08 | 1999-07-27 | Basf Aktiengesellschaft | Preparation of Bisoximes |
US6057352A (en) * | 1995-05-17 | 2000-05-02 | E. I. Du Pont De Nemours And Company | Fungicidal cyclic amides |
CN1068596C (zh) * | 1995-06-22 | 2001-07-18 | 诺瓦提斯公司 | 农药用的三-肟基杂环化合物 |
SK598A3 (en) * | 1995-07-04 | 1998-06-03 | Novartis Ag | Triazoline and isoxazoline bis-oxime derivatives and their use as pesticides |
EP0842144B1 (de) * | 1995-07-27 | 2001-10-31 | Basf Aktiengesellschaft | Phenylessigsäurederivate, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung als schädlingsbekämpfungsmittel und fungizide |
DE19528651A1 (de) * | 1995-08-04 | 1997-02-06 | Basf Ag | Hydroximsäurederivate, Verfahren zu ihrer Herstellung und sie enthaltende Mittel |
ATE374188T1 (de) * | 1995-08-15 | 2007-10-15 | Bayer Cropscience Ag | Pestizide indazol-derivate |
CZ34498A3 (cs) * | 1995-08-17 | 1998-06-17 | Basf Aktiengesellschaft | Fungicidní směs |
US5939454A (en) * | 1995-08-17 | 1999-08-17 | Basf Akdtiengesellschaft | Fungicidal mixtures of an oxime ether carboxylic acit amide with a dithiocarbamate |
DE59603362D1 (de) * | 1995-08-17 | 1999-11-18 | Basf Ag | Fungizide mischungen eines oximethercarbonsäureamids mit fenarimol |
WO1997006679A1 (de) * | 1995-08-17 | 1997-02-27 | Basf Aktiengesellschaft | Fungizide mischungen |
JPH11511145A (ja) * | 1995-08-17 | 1999-09-28 | ビーエーエスエフ アクチェンゲゼルシャフト | 殺菌剤混合物 |
JPH11511143A (ja) * | 1995-08-17 | 1999-09-28 | ビーエーエスエフ アクチェンゲゼルシャフト | 殺菌剤混合物 |
AR004012A1 (es) | 1995-10-10 | 1998-09-30 | Basf Ag | Derivados de acido fenilacetico, procedimientos para su obtencion, su uso para preparar composiciones para combatir animales u hongos nocivos, lascomposiciones asi obtenidas y los procedimientos de aplicacion de dichas composiciones. |
DE19539324A1 (de) * | 1995-10-23 | 1997-04-24 | Basf Ag | Phenylessigsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung und sie enthaltende Mittel |
DE19540361A1 (de) * | 1995-10-30 | 1997-05-07 | Basf Ag | Phenylessigsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schadpilzen und tierischen Schädlingen |
JPH11514632A (ja) * | 1995-11-02 | 1999-12-14 | ビーエーエスエフ アクチェンゲゼルシャフト | ピリジル酢酸誘導体、その製造方法ならびに製造用中間体、及びその用途 |
DE19540989A1 (de) * | 1995-11-03 | 1997-05-07 | Basf Ag | Pyridylessigsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung und sie enthaltende Mittel |
DE19542629A1 (de) * | 1995-11-15 | 1997-05-22 | Basf Ag | Azinooximether, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schadpilzen und tierischen Schädlingen |
DE19545094A1 (de) * | 1995-12-04 | 1997-06-05 | Basf Ag | Phenylessigsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung und sie enthaltende Mittel |
NZ323666A (ru) * | 1995-12-07 | 2000-01-28 | Novartis Ag | |
IL124451A0 (en) * | 1995-12-07 | 1998-12-06 | Novartis Ag | Process for the preparation of pesticides |
DE19548783A1 (de) * | 1995-12-27 | 1997-07-03 | Basf Ag | Cyaniminooximether, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schadpilzen und tierischen Schädlingen |
EP0782982B1 (de) * | 1996-01-03 | 2000-05-17 | Novartis AG | Verfahren zur Herstellung o-Chlor-Methyl-Phenylglyoxylsäure-Derivaten |
AU2178697A (en) * | 1996-04-11 | 1997-10-29 | Shionogi & Co., Ltd. | Alpha-alkoxyiminobenzyl derivatives and agricultural chemicals containing them as active ingredients |
EP0912499B1 (en) * | 1996-06-12 | 2001-12-12 | Bayer Aktiengesellschaft | Pesticides |
US5973001A (en) * | 1996-08-05 | 1999-10-26 | Basf Aktiengesellshcaft | Fungicidal mixtures of an oxime ether carboxylic acid amide with cymoxanil |
WO1998028262A1 (en) * | 1996-12-20 | 1998-07-02 | Novartis Ag | O-benzyl oxime ether derivatives as pecticides |
DE19708940A1 (de) | 1997-03-05 | 1998-09-10 | Basf Ag | Hydroximsäurehalogenide, Verfahren zur ihrer Herstellung und ihre Verwendung |
AR015821A1 (es) * | 1997-05-27 | 2001-05-30 | Bayer Ag | Compuestos organicos |
AU8210298A (en) * | 1997-05-27 | 1998-12-30 | Novartis Ag | O-benzyl oxime ethers and their use as pesticides |
CO5050364A1 (es) | 1997-05-28 | 2001-06-27 | Basf Ag | Metodo para controlar hongos nocivos |
WO1998053692A1 (de) | 1997-05-30 | 1998-12-03 | Basf Aktiengesellschaft | Fungizide mischungen |
IL132932A0 (en) | 1997-06-04 | 2001-03-19 | Basf Ag | Fungicidal mixtures |
GB9718366D0 (en) | 1997-08-29 | 1997-11-05 | Ciba Geigy Ag | Novel combinations |
EP1077953A2 (de) * | 1998-05-14 | 2001-02-28 | Basf Aktiengesellschaft | Bisoximetherderivate, zwischenprodukte und verwendung zur bekämpfung von schadpilzen und tierischen schädlingen |
US6313344B1 (en) | 1998-05-27 | 2001-11-06 | Bayer Aktiengesellschaft | Organic compounds |
ES2241327T3 (es) | 1998-09-22 | 2005-10-16 | Bayer Cropscience Ag | Compuestos pesticidas de bis-oxima. |
GB9820582D0 (en) * | 1998-09-22 | 1998-11-11 | Novartis Ag | Organic compounds |
CN1326436A (zh) * | 1998-11-20 | 2001-12-12 | 巴斯福股份公司 | 制备链烯基取代二肟醚衍生物的方法 |
GB9827163D0 (en) | 1998-12-10 | 1999-02-03 | Novartis Ag | Organic compounds |
JP2002531540A (ja) * | 1998-12-10 | 2002-09-24 | バイエル アクチェンゲゼルシャフト | ストロビルリン中間体の製造方法 |
AU1007400A (en) * | 1999-01-27 | 2000-08-03 | Dow Agrosciences Llc | Aryl and heteroarylcyclopropyl oxime ethers and their use as fungicides and insecticides |
GB9908530D0 (en) | 1999-04-14 | 1999-06-09 | Novartis Ag | Organic compounds |
AU2362401A (en) * | 1999-12-06 | 2001-06-18 | Bayer Aktiengesellschaft | N-phenylcarbamates having a microbicide, insecticide and acaricide effect |
JP4658432B2 (ja) | 1999-12-07 | 2011-03-23 | ビーエーエスエフ ソシエタス・ヨーロピア | o−クロロメチルベンゾイルクロリドの製造方法 |
ES2213670T3 (es) * | 2000-01-21 | 2004-09-01 | Dow Agrosciences Llc | Aril y heteroarilciclopropiloxima-eteres y sus usos como fungicidas e insecticidas. |
US6313339B1 (en) | 2000-02-17 | 2001-11-06 | Ronald Ross, Jr. | Aryl and heteroarylcylopropyl oxime ethers and their use as fungicides and insecticides |
KR100422883B1 (ko) * | 2001-03-26 | 2004-03-12 | 학교법인고려중앙학원 | 항균물질 페닐아세틱 에시드 및 소디움 페닐아세테이트을유효성분으로 하는 고추역병 방제용 살균제 조성물 |
DE10209145A1 (de) * | 2002-03-01 | 2003-09-04 | Bayer Cropscience Ag | Halogenbenzole |
ES2309392T3 (es) | 2002-11-12 | 2008-12-16 | Basf Se | Procedimiento para el aumento del rendimiento en leguminosas resistentes a los glifosatos. |
US7161026B1 (en) | 2005-07-08 | 2007-01-09 | Property Development Corporation International, Ltd, Inc. | Method of preparation of methyl-benzyl-ketone |
DE602006012716D1 (de) * | 2005-10-28 | 2010-04-15 | Basf Se | Verfahren zur induktion von resistenz gegen schadpilze |
EP1998614A2 (en) * | 2006-03-10 | 2008-12-10 | Basf Se | Method for improving the tolerance of plants to chilling temperatures and/or frost |
JP2009529565A (ja) * | 2006-03-14 | 2009-08-20 | ビーエーエスエフ ソシエタス・ヨーロピア | 細菌症に対する植物の耐性を誘導する方法 |
ES2610030T3 (es) | 2006-03-24 | 2017-04-25 | Basf Se | Método para combatir la enfermedad de la yesca |
EP2392662A3 (en) | 2007-04-23 | 2012-03-14 | Basf Se | Plant productivity enhancement by combining chemical agents with transgenic modifications |
US20120321587A1 (en) * | 2009-07-09 | 2012-12-20 | Elias Rosen | Compositions and methods of use pertaining to insecticide |
CN102469791A (zh) | 2009-07-28 | 2012-05-23 | 巴斯夫欧洲公司 | 用于增加多年生植物的贮藏组织中游离氨基酸水平的方法 |
JP2013505910A (ja) | 2009-09-25 | 2013-02-21 | ビーエーエスエフ ソシエタス・ヨーロピア | 植物の雌花の発育不全を減少させる方法 |
US20130085066A1 (en) * | 2010-05-31 | 2013-04-04 | Basf Se | Method for Increasing the Health of a Plant |
EP3047731A1 (en) | 2015-01-21 | 2016-07-27 | Basf Se | Method for combating soybean rust comprising treating soybean with (2E)-2-[3-substituted-2 [[(E)-[(2E)-2-alkoxyimino-1-methyl-2-phenyl-ethylidene]amino]oxymethyl]phenyl]-2-methoxy-imino-N-methyl-acetamides |
AR115870A1 (es) | 2018-07-31 | 2021-03-10 | Sumitomo Chemical Co | MÉTODO PARA CONTROLAR EL HONGO DE LA ROYA DE LA SOJA QUE TIENE RESISTENCIA AL INHIBIDOR DE SITIO Qₒ |
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DE2621102A1 (de) * | 1976-05-10 | 1977-11-24 | Schering Ag | Propan-1,2-diondioxime, schaedlingsbekaempfungsmittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung |
DE3039269A1 (de) * | 1980-10-17 | 1982-05-19 | Bayer Ag, 5090 Leverkusen | Hydroxamsaeureester, verfahren zu ihrer herstellung, ihre verwendung in schaedlingsbekaempfungsmitteln und zwischenprodukte dafuer |
ES2054025T5 (es) * | 1988-11-21 | 1998-02-16 | Zeneca Ltd | Fungicidas. |
HUT52421A (en) * | 1988-12-23 | 1990-07-28 | Janos Puglits | Control gear for automatic operating the clutch of motor vehicles |
AU4639089A (en) * | 1988-12-29 | 1990-08-01 | Ciba-Geigy Ag | Methyl esters of aldimino- or ketimino-oxy-ortho-tolylacrylic acid, manufacturing process and fungicides containing them |
US5104872A (en) * | 1989-08-22 | 1992-04-14 | Nihon Hohyaku Co., Ltd. | N-(substituted benzyloxy) imine derivatives and method of use thereof |
PH11991042549B1 (ru) * | 1990-06-05 | 2000-12-04 | ||
DK0463488T4 (da) * | 1990-06-27 | 2004-05-10 | Basf Ag | 0-benzyloximethere og plantebeskyttelsesmidler indeholdende disse forbindelser |
GB9018408D0 (en) * | 1990-08-22 | 1990-10-03 | Ici Plc | Fungicides |
DK0569384T4 (da) * | 1991-01-30 | 2000-12-04 | Zeneca Ltd | Fungicider |
NZ242290A (en) * | 1991-04-15 | 1994-12-22 | Zeneca Ltd | Pyridyl and pyrimidinyl substituted oxime-o-benzyl ether derivatives; preparatory processes, fungicidal compositions and an intermediate |
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. |
EP0738260B2 (en) * | 1994-01-05 | 2006-12-13 | Bayer CropScience AG | Pesticides |
ATE195509T1 (de) * | 1994-02-04 | 2000-09-15 | Basf Ag | Phenylessigsäurederivate, verfahren und zwischenprodukte zu ihrer herstellung und sie enthaltende mittel |
WO1995021154A2 (de) * | 1994-02-04 | 1995-08-10 | Basf Aktiengesellschaft | Phenylessigsäurederivate, verfahren und zwischenprodukte zu ihrer herstellung und sie enthaltende mittel |
SK283068B6 (sk) * | 1994-06-10 | 2003-02-04 | Basf Aktiengesellschaft | Spôsob prípravy derivátu metylamidu alfa-metoxyiminokarboxylovej kyseliny a medziprodukty na ich prípravu |
-
1994
- 1994-12-27 EP EP95905110A patent/EP0738260B2/en not_active Expired - Lifetime
- 1994-12-27 CZ CZ19961990A patent/CZ291625B6/cs not_active IP Right Cessation
- 1994-12-27 WO PCT/EP1994/004318 patent/WO1995018789A1/en active IP Right Grant
- 1994-12-27 HU HU9601839A patent/HU219157B/hu not_active IP Right Cessation
- 1994-12-27 CN CNB941947785A patent/CN1152007C/zh not_active Expired - Fee Related
- 1994-12-27 AU AU13851/95A patent/AU690190B2/en not_active Ceased
- 1994-12-27 CA CA002179418A patent/CA2179418C/en not_active Expired - Fee Related
- 1994-12-27 MD MD96-0291A patent/MD1315C2/ru unknown
- 1994-12-27 SK SK880-96A patent/SK88096A3/sk unknown
- 1994-12-27 AP APAP/P/1996/000820A patent/AP654A/en active
-
1995
- 1995-01-03 IL IL11222795A patent/IL112227A/xx not_active IP Right Cessation
- 1995-09-11 US US08/526,859 patent/US5756426A/en not_active Expired - Lifetime
-
1996
- 1996-07-01 FI FI962712A patent/FI962712A/fi unknown
- 1996-07-04 NO NO962823A patent/NO307045B1/no not_active IP Right Cessation
- 1996-07-24 LV LVP-96-314A patent/LV11684B/en unknown
-
1997
- 1997-11-12 US US08/968,143 patent/US5981585A/en not_active Expired - Fee Related
-
1999
- 1999-06-22 US US09/338,236 patent/US6313166B1/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
NO962823D0 (no) | 1996-07-04 |
CN1141032A (zh) | 1997-01-22 |
HU9601839D0 (en) | 1996-10-28 |
US5981585A (en) | 1999-11-09 |
CN1152007C (zh) | 2004-06-02 |
HU219157B (hu) | 2001-02-28 |
EP0738260A1 (en) | 1996-10-23 |
AP9600820A0 (en) | 1996-07-31 |
FI962712A (fi) | 1996-08-16 |
EP0738260B2 (en) | 2006-12-13 |
LV11684B (en) | 1997-06-20 |
AU1385195A (en) | 1995-08-01 |
MD1315C2 (ru) | 2000-06-30 |
AU690190B2 (en) | 1998-04-23 |
CA2179418C (en) | 2004-06-22 |
US5756426A (en) | 1998-05-26 |
MD960291A (en) | 1997-10-31 |
HUT74980A (en) | 1997-03-28 |
IL112227A0 (en) | 1995-03-30 |
FI962712A0 (fi) | 1996-07-01 |
EP0738260B1 (en) | 2001-08-29 |
CZ199096A3 (en) | 1996-10-16 |
CA2179418A1 (en) | 1995-07-13 |
MD1315B1 (en) | 1999-09-30 |
WO1995018789A1 (en) | 1995-07-13 |
NO307045B1 (no) | 2000-01-31 |
US6313166B1 (en) | 2001-11-06 |
LV11684A (lv) | 1997-02-20 |
CZ291625B6 (cs) | 2003-04-16 |
IL112227A (en) | 1999-11-30 |
AP654A (en) | 1998-07-31 |
NO962823L (no) | 1996-07-04 |
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