RU2174981C2 - Производные нафтохинона, инсектицидноакарицидная и/или фунгицидная композиция, способ борьбы с грибками, и/или насекомыми, и/или акаридами - Google Patents
Производные нафтохинона, инсектицидноакарицидная и/или фунгицидная композиция, способ борьбы с грибками, и/или насекомыми, и/или акаридами Download PDFInfo
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- RU2174981C2 RU2174981C2 RU98102154/04A RU98102154A RU2174981C2 RU 2174981 C2 RU2174981 C2 RU 2174981C2 RU 98102154/04 A RU98102154/04 A RU 98102154/04A RU 98102154 A RU98102154 A RU 98102154A RU 2174981 C2 RU2174981 C2 RU 2174981C2
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- alkyl
- silicon atom
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- 239000000203 mixture Substances 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 29
- 241000238631 Hexapoda Species 0.000 title claims abstract description 16
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 13
- 241000233866 Fungi Species 0.000 title claims abstract description 8
- 229930192627 Naphthoquinone Natural products 0.000 title claims abstract description 8
- 150000002791 naphthoquinones Chemical class 0.000 title claims abstract description 7
- 239000000417 fungicide Substances 0.000 title abstract description 7
- 239000000642 acaricide Substances 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 103
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 39
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 8
- 230000000895 acaricidal effect Effects 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- 239000002917 insecticide Substances 0.000 claims abstract description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract description 3
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000004429 atom Chemical group 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 230000000749 insecticidal effect Effects 0.000 claims description 3
- 230000000694 effects Effects 0.000 abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 73
- 239000000243 solution Substances 0.000 description 51
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- -1 4- (trimethylsilyl) cyclohexyl group Chemical group 0.000 description 25
- 238000002360 preparation method Methods 0.000 description 25
- 239000002904 solvent Substances 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 19
- 238000012360 testing method Methods 0.000 description 19
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 125000005843 halogen group Chemical group 0.000 description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 241001124076 Aphididae Species 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 244000045947 parasite Species 0.000 description 9
- 230000000361 pesticidal effect Effects 0.000 description 9
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 8
- 241000238876 Acari Species 0.000 description 7
- 229920001817 Agar Polymers 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 125000000547 substituted alkyl group Chemical group 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 241000258937 Hemiptera Species 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000008272 agar Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 125000001188 haloalkyl group Chemical group 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 5
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 125000004438 haloalkoxy group Chemical group 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VALIZEALBKQSTK-UHFFFAOYSA-N (1,4-dioxonaphthalen-2-yl) benzoate Chemical compound C=1C(=O)C2=CC=CC=C2C(=O)C=1OC(=O)C1=CC=CC=C1 VALIZEALBKQSTK-UHFFFAOYSA-N 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- DKARGJVZDRZMHK-UHFFFAOYSA-N C1=CC=C2C(=O)C(CCCCCCCCC[Si](C)(C)C)=C(O)C(=O)C2=C1 Chemical compound C1=CC=C2C(=O)C(CCCCCCCCC[Si](C)(C)C)=C(O)C(=O)C2=C1 DKARGJVZDRZMHK-UHFFFAOYSA-N 0.000 description 4
- RXCDXHNXBBLGIO-UHFFFAOYSA-N C1=CC=C2C(=O)C(CC[Si](C)(C)C)=C(O)C(=O)C2=C1 Chemical compound C1=CC=C2C(=O)C(CC[Si](C)(C)C)=C(O)C(=O)C2=C1 RXCDXHNXBBLGIO-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 241000255925 Diptera Species 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- VUJXYXATYOHEQJ-UHFFFAOYSA-N [1,4-dioxo-3-(2-trimethylsilylethyl)naphthalen-2-yl] benzoate Chemical compound O=C1C2=CC=CC=C2C(=O)C(CC[Si](C)(C)C)=C1OC(=O)C1=CC=CC=C1 VUJXYXATYOHEQJ-UHFFFAOYSA-N 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 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 description 4
- FRASJONUBLZVQX-UHFFFAOYSA-N naphthoquinone group Chemical group C1(C=CC(C2=CC=CC=C12)=O)=O FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- OPKFWRVRCVCMJH-UHFFFAOYSA-N 6-methylnaphthalene-1,4-dione Chemical compound O=C1C=CC(=O)C2=CC(C)=CC=C21 OPKFWRVRCVCMJH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000254173 Coleoptera Species 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000813090 Rhizoctonia solani Species 0.000 description 3
- HEJMMSVGUGXBRA-UHFFFAOYSA-N [1,4-dioxo-3-(2-trimethylsilylethyl)naphthalen-2-yl] acetate Chemical compound C1=CC=C2C(=O)C(OC(=O)C)=C(CC[Si](C)(C)C)C(=O)C2=C1 HEJMMSVGUGXBRA-UHFFFAOYSA-N 0.000 description 3
- 125000003302 alkenyloxy group Chemical group 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000005133 alkynyloxy group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004177 carbon cycle Methods 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000004465 cycloalkenyloxy group Chemical group 0.000 description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 125000005415 substituted alkoxy group Chemical group 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 2
- 229940005561 1,4-benzoquinone Drugs 0.000 description 2
- BXXWFOGWXLJPPA-UHFFFAOYSA-N 2,3-dibromobutane Chemical compound CC(Br)C(C)Br BXXWFOGWXLJPPA-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- QMMDUTMJSOUXCV-UHFFFAOYSA-N 2-(ethoxymethoxy)-3-(9-trimethylsilylnonyl)naphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(OCOCC)=C(CCCCCCCCC[Si](C)(C)C)C(=O)C2=C1 QMMDUTMJSOUXCV-UHFFFAOYSA-N 0.000 description 2
- 241000228245 Aspergillus niger Species 0.000 description 2
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 2
- 235000000536 Brassica rapa subsp pekinensis Nutrition 0.000 description 2
- 241000499436 Brassica rapa subsp. pekinensis Species 0.000 description 2
- GTBYUBMMSBUTSV-UHFFFAOYSA-N C1=CC=C2C(=O)C(C=CC[Si](C)(C)C)=C(O)C(=O)C2=C1 Chemical compound C1=CC=C2C(=O)C(C=CC[Si](C)(C)C)=C(O)C(=O)C2=C1 GTBYUBMMSBUTSV-UHFFFAOYSA-N 0.000 description 2
- ZKPVFBHFQZTKIS-UHFFFAOYSA-N C1=CC=C2C(=O)C(CCCCCCCC[Si](C)(C)CC)=C(O)C(=O)C2=C1 Chemical compound C1=CC=C2C(=O)C(CCCCCCCC[Si](C)(C)CC)=C(O)C(=O)C2=C1 ZKPVFBHFQZTKIS-UHFFFAOYSA-N 0.000 description 2
- YKUUENWXCHOHRZ-UHFFFAOYSA-N C1=CC=C2C(=O)C(CCCCC[Si](C)(C)C)=C(O)C(=O)C2=C1 Chemical compound C1=CC=C2C(=O)C(CCCCC[Si](C)(C)C)=C(O)C(=O)C2=C1 YKUUENWXCHOHRZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920006358 Fluon Polymers 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 241001330975 Magnaporthe oryzae Species 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- 241000257226 Muscidae Species 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 241001608567 Phaedon cochleariae Species 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 241001454294 Tetranychus Species 0.000 description 2
- ACOOKSMODFIBIR-UHFFFAOYSA-N [1,4-dioxo-3-(9-trimethylsilylnonyl)naphthalen-2-yl] acetate Chemical compound C1=CC=C2C(=O)C(OC(=O)C)=C(CCCCCCCCC[Si](C)(C)C)C(=O)C2=C1 ACOOKSMODFIBIR-UHFFFAOYSA-N 0.000 description 2
- AGIMOMGYWZCZDF-UHFFFAOYSA-N [1,4-dioxo-3-(9-trimethylsilylnonyl)naphthalen-2-yl] propanoate Chemical compound C1=CC=C2C(=O)C(OC(=O)CC)=C(CCCCCCCCC[Si](C)(C)C)C(=O)C2=C1 AGIMOMGYWZCZDF-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000005082 alkoxyalkenyl group Chemical group 0.000 description 2
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- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000000262 haloalkenyl group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000002035 hexane extract Substances 0.000 description 2
- 238000003898 horticulture Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- CSFWPUWCSPOLJW-UHFFFAOYSA-N lawsone Chemical compound C1=CC=C2C(=O)C(O)=CC(=O)C2=C1 CSFWPUWCSPOLJW-UHFFFAOYSA-N 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
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- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
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- 229910001961 silver nitrate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
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Images
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9513550.5 | 1995-07-04 | ||
| GBGB9513550.5A GB9513550D0 (en) | 1995-07-04 | 1995-07-04 | Pesticidal compounds |
| US60/001,103 | 1995-07-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU98102154A RU98102154A (ru) | 1999-12-20 |
| RU2174981C2 true RU2174981C2 (ru) | 2001-10-20 |
Family
ID=10777070
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU98102154/04A RU2174981C2 (ru) | 1995-07-04 | 1996-07-04 | Производные нафтохинона, инсектицидноакарицидная и/или фунгицидная композиция, способ борьбы с грибками, и/или насекомыми, и/или акаридами |
Country Status (5)
| Country | Link |
|---|---|
| AR (1) | AR003965A1 (enrdf_load_stackoverflow) |
| GB (1) | GB9513550D0 (enrdf_load_stackoverflow) |
| IN (1) | IN185299B (enrdf_load_stackoverflow) |
| RU (1) | RU2174981C2 (enrdf_load_stackoverflow) |
| ZA (1) | ZA965684B (enrdf_load_stackoverflow) |
-
1995
- 1995-07-04 GB GBGB9513550.5A patent/GB9513550D0/en active Pending
-
1996
- 1996-07-04 IN IN1478DE1996 patent/IN185299B/en unknown
- 1996-07-04 ZA ZA9605684A patent/ZA965684B/xx unknown
- 1996-07-04 RU RU98102154/04A patent/RU2174981C2/ru not_active IP Right Cessation
- 1996-07-04 AR ARP960103445A patent/AR003965A1/es not_active Application Discontinuation
Non-Patent Citations (1)
| Title |
|---|
| HENTON D.R. et al - 7. Org. Chem. v 45, N 17, 1980. 3422 - 3433. BALZER B.L. et al - 7. Am. Chem. Soc, v 144, N 22, 1992, 8735 - 8736. * |
Also Published As
| Publication number | Publication date |
|---|---|
| GB9513550D0 (en) | 1995-09-06 |
| AR003965A1 (es) | 1998-09-30 |
| IN185299B (enrdf_load_stackoverflow) | 2000-12-23 |
| ZA965684B (en) | 1998-01-05 |
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